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Acta Crystallogr Sect E Struct Rep Online. 2012 February 1; 68(Pt 2): o473–o474.
Published online 2012 January 21. doi:  10.1107/S1600536812001432
PMCID: PMC3275224
Copyright © Yusufzai et al. 2012
3β-Acet­oxy-5α-cholestan-6-one 2-cyano­acetyl­hydrazone
Samina Khan Yusufzai,a Hasnah Osman,a‡ Othman Sulaiman,b Suhana Arshad,c and Ibrahim Abdul Razakc*§
aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
bSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki/at/usm.my
‡Additional correspondence email: ohasnah@usm.my.
§Thomson Reuters ResearcherID: A-5599-2009.
Received November 30, 2011; Accepted January 12, 2012.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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Abstract
The asymmetric unit of the title compound, C32H51N3O3, consists of two crystallographically independent mol­ecules, A and B; the 2-methyl­pentane group of mol­ecule A and the propane group of mol­ecule B are each disordered over two sets of sites, with refined site-occupancies of 0.825 (5):0.175 (5) and 0.630 (18):0.370 (18), respectively. In both mol­ecules, the three cyclo­hexane rings in the steroid fused ring systems adopt chair conformations while the cyclo­pentane rings adopt envelope and twist conformations in mol­ecules A and B, respectively. In the crystal, N—H(...)O and C—H(...)O hydrogen bonds link the two independent mol­ecules together, generating R 2 1(7) and R 2 2(8) ring motifs.
For the biological activity of steroidal derivatives, see: Khan & Yusuf (2009 [triangle]); Drach et al. (2000 [triangle]); Gupta et al. (1995 [triangle]); Ahmed & Boruah (1996 [triangle]); Short & Long (1969 [triangle]); Khan et al. (2007 [triangle]); Doorenbos & Wu (1968 [triangle]); Banday et al. (2010 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Khan et al. (2011 [triangle]); Ketuly et al. (2011 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).
An external file that holds a picture, illustration, etc. Object name is e-68-0o473-scheme1.jpg Object name is e-68-0o473-scheme1.jpg
Crystal data
  • C32H51N3O3
  • M r = 525.76
  • Monoclinic, An external file that holds a picture, illustration, etc. Object name is e-68-0o473-efi1.jpg
  • a = 17.1691 (2) Å
  • b = 9.6694 (1) Å
  • c = 19.1447 (3) Å
  • β = 109.171 (1)°
  • V = 3002.04 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 K
  • 0.32 × 0.18 × 0.09 mm
Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.977, T max = 0.994
  • 40102 measured reflections
  • 9291 independent reflections
  • 6778 reflections with I > 2σ(I)
  • R int = 0.081
Refinement
  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.117
  • S = 1.01
  • 9291 reflections
  • 752 parameters
  • 48 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.26 e Å−3
Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001432/is5021sup1.cif
Click here to view.(76K, cif)
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001432/is5021Isup2.hkl
Click here to view.(454K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the FRGS grant (203/PKIMIA/6711179) and the Research University grant No.1001/PFIZIK/811151 to conduct this work. SKY also thanks USM for providing Graduate Assistance financial support.
supplementary crystallographic information
Comment
A literature survey reveals that steroids are compounds of biological origin and play an important role in biological systems. During the last decade the major efforts of the chemists were directed towards the modification in the structure of steroids in order to enhance their biologically activity (Khan & Yusuf, 2009; Drach et al., 2000). Many of these steroidal derivatives, were found to possess antimicrobial, anti-cancer, anti-inflammatory, anti-tuberculosis, hypotensive, anti-convulsant and diuretic activities (Gupta et al., 1995; Ahmed & Boruah, 1996; Short & Long, 1969; Khan et al., 2007; Doorenbos & Wu, 1968; Banday et al., 2010). In the present work, we have synthesized a new compound, 3β-acetoxy-5α-cholestan-6-one-cyanoacetohydrazone which corresponds to the molecular formula C32H51N3O3. Synthesis of other derivatives of steroidal cyanoacetohydrazone and their biological activities are under progress.
The asymmetric unit of the title compound consists of two crystallographically independent molecules A and B (Fig. 1). The 2-methylpentane group of molecule A and the propane group of molecule B are disordered with refined site-occupancies of 0.825 (5): 0.175 (5) and 0.630 (18): 0.370 (18), respectively. For each molecules, the three cyclohexane rings in the steroid fused ring system adopt a chair conformation [Molecule A (C1A–C3A/C8A/C9A/C17A):(C3A–C8A): (C9A–C12A/C16A/C17A); Q= 0.545 (3):0.562 (3):0.569 (3) Å, Θ= 161.2 (3): 178.7 (3):176.4 (3)° and Φ= 21.3 (9):232 (10):24 (4)°; Molecule B (C1B–C3B/C8B/C9B/C17B):(C3B–C8B):(C9B–C12B/C16B/C17B); Q= 0.597 (3): 0.590 (3):0.593 (3) Å, Θ= 167.1 (3):172.9 (3):175.2 (3)° and Φ= 311.6 (12):294 (2):102 (3)°]. On the other hand, the cyclopentane ring of the steroid fused ring system in both molecules adopts a different ring conformation (Cremer & Pople, 1975). The cyclopentane (C12A–C16A) ring of molecule A is in an envelope conformation with puckering parameters Q= 0.469 (3) Å and [var phi]= 351.6 (4)° with atom C12A at the flap. Meanwhile, molecule B is in a twist conformation where the cyclopentane (C12B–C16B) ring is twisted about C16B–C12B bonds, with puckering parameters Q= 0.464 (3) Å and [var phi]= 350.2 (4)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Khan et al., 2011; Ketuly et al., 2011).
The crystal packing is shown in Fig. 2. Molecule A and B are interconnected via N2A—H1NA···O3B, N2B—H1NB···O3A and C1A—H1AB···O3B intermolecular hydrogen bonds (Table 1), generating R12(7) and R22(8) ring motifs (Bernstein et al., 1995).
Experimental
To a solution of steroidal ketone, 3β-acetoxy-5α-cholestan-6-one, (5 mmol) in absolute ethanol (10 ml) was added cyanoacetichydrazide (10 mmol) followed by few drops of triethylamine. The reaction mixture was refluxed for 24 h. The progress of reaction was monitored by thin layer chromatography. After completion of the reaction, reaction mixture was concentrated under reduce pressure. The obtained solid, was extracted with ether and ethereal layer was washed with water, NaHCO3 solution (5%) and dried over anhydrous sodium sulfate. The solvent was evaporated and the product was recrystallized from ethanol resulting in shiny crystals.
Refinement
The propane group of molecule A was disordered over two positions with refined site-occupancies of 0.825 (5):0.175 (5). The minor disordered components were refined isotropically. For molecule B, the 2-methylpentane group was disordered over two positions with refined site-occupancies of 0.630 (18):0.370 (18). N-bound H atoms was located from the difference map and refined freely, [N—H = 0.85 (3) and 0.88 (3) Å]. The remaining H atoms were positioned geometrically [C—H = 0.96–0.98 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. Since there are not sufficient anomalous dispersion to determine the absolute configuration, 8296 Friedel pairs were merged for the final refinement. The same Uij parameter was used for atoms pair C30X/C31X. Similarity and rigid bond restraints was also used in the final refinement.
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. All disordered components are shown.
Fig. 2.
Fig. 2.
The crystal packing of the title compound. Only major disordered components is shown.
Crystal data
C32H51N3O3F(000) = 1152
Mr = 525.76Dx = 1.163 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5129 reflections
a = 17.1691 (2) Åθ = 2.9–30.1°
b = 9.6694 (1) ŵ = 0.07 mm−1
c = 19.1447 (3) ÅT = 100 K
β = 109.171 (1)°Plate, colourless
V = 3002.04 (7) Å30.32 × 0.18 × 0.09 mm
Z = 4
Data collection
Bruker SMART APEXII CCD area-detector diffractometer9291 independent reflections
Radiation source: fine-focus sealed tube6778 reflections with I > 2σ(I)
graphiteRint = 0.081
[var phi] and ω scansθmax = 30.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −24→24
Tmin = 0.977, Tmax = 0.994k = −13→13
40102 measured reflectionsl = −26→26
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0539P)2 + 0.0496P] where P = (Fo2 + 2Fc2)/3
9291 reflections(Δ/σ)max = 0.001
752 parametersΔρmax = 0.27 e Å−3
48 restraintsΔρmin = −0.26 e Å−3
Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/UeqOcc. (<1)
O1A0.57377 (11)0.8338 (2)0.71592 (11)0.0267 (5)
O2A0.56068 (14)1.0550 (3)0.67883 (13)0.0452 (6)
O3A0.90699 (10)0.7992 (2)0.49807 (10)0.0247 (4)
N1A0.83483 (12)0.7956 (2)0.64950 (11)0.0172 (4)
N2A0.88885 (13)0.7881 (2)0.60893 (12)0.0181 (4)
N3A0.72058 (15)0.6629 (3)0.37315 (14)0.0329 (6)
C1A0.95621 (14)0.7990 (3)0.76523 (14)0.0209 (6)
H1AA0.97590.89370.77260.025*
H1AB0.98570.75230.73660.025*
C2A0.86589 (14)0.8009 (3)0.72046 (14)0.0164 (5)
C3A0.80581 (15)0.8246 (3)0.76226 (13)0.0175 (5)
H3AA0.81480.92010.78010.021*
C4A0.71486 (15)0.8168 (3)0.71406 (15)0.0212 (5)
H4AA0.70470.87940.67240.025*
H4AB0.70180.72370.69490.025*
C5A0.66004 (15)0.8559 (3)0.75950 (15)0.0230 (6)
H5AA0.66870.95340.77400.028*
C6A0.67590 (15)0.7673 (3)0.82741 (15)0.0270 (6)
H6AA0.66000.67260.81270.032*
H6AB0.64260.80000.85630.032*
C7A0.76765 (15)0.7717 (3)0.87501 (14)0.0241 (6)
H7AA0.78090.86420.89500.029*
H7AB0.77650.70870.91630.029*
C8A0.82676 (15)0.7330 (3)0.83276 (14)0.0167 (5)
C9A0.91689 (14)0.7667 (3)0.88116 (13)0.0156 (5)
H9AA0.91970.86750.88670.019*
C10A0.94319 (15)0.7075 (3)0.95982 (13)0.0197 (5)
H10A0.93760.60760.95700.024*
H10B0.90650.74250.98490.024*
C11A1.03259 (14)0.7448 (3)1.00555 (14)0.0201 (5)
H11A1.03660.84381.01390.024*
H11B1.04700.69951.05330.024*
C12A1.09402 (15)0.7013 (3)0.96700 (13)0.0169 (5)
C13A1.18305 (14)0.7622 (3)0.99766 (14)0.0192 (5)
H13A1.17770.86071.00730.023*
C14A1.21409 (15)0.7522 (3)0.93005 (13)0.0195 (5)
H14A1.24680.83290.92790.023*
H14B1.24790.67040.93390.023*
C15A1.13686 (14)0.7442 (3)0.85991 (14)0.0198 (5)
H15A1.13840.81500.82450.024*
H15B1.13250.65420.83660.024*
C16A1.06532 (14)0.7688 (3)0.88967 (13)0.0166 (5)
H16A1.06390.86860.89800.020*
C17A0.97830 (14)0.7285 (3)0.84107 (13)0.0165 (5)
H17A0.97660.62810.83370.020*
C18A0.85976 (14)0.7953 (3)0.53426 (14)0.0183 (5)
C19A0.76648 (15)0.8000 (3)0.49751 (14)0.0213 (5)
H19A0.74000.75930.53030.026*
H19B0.74860.89540.48860.026*
C20A0.74160 (16)0.7241 (3)0.42715 (15)0.0229 (6)
C21A0.53096 (18)0.9421 (4)0.67993 (17)0.0306 (7)
C22A0.44342 (17)0.9025 (4)0.63900 (18)0.0406 (8)
H22A0.41090.98450.62330.061*
H22B0.42180.84960.67100.061*
H22C0.44140.84800.59650.061*
C23A0.81746 (17)0.5795 (3)0.81186 (16)0.0235 (6)
H23A0.83940.52430.85560.035*
H23B0.84700.56000.77820.035*
H23C0.76010.55810.78860.035*
C24A1.09831 (16)0.5431 (3)0.96309 (15)0.0220 (6)
H24A1.04680.50820.93070.033*
H24B1.10900.50491.01160.033*
H24C1.14180.51730.94450.033*
C25A1.21170 (17)0.6917 (3)1.13305 (14)0.0248 (6)
H25A1.16820.62441.12230.037*
H25B1.19060.78041.14050.037*
H25C1.25530.66501.17700.037*
C26A1.24532 (16)0.7000 (3)1.06800 (14)0.0242 (6)
H26B1.25950.60641.05660.029*0.825 (5)
H26C1.24490.60241.05410.029*0.175 (5)
C27A1.3267 (2)0.7912 (5)1.0919 (2)0.0233 (8)0.825 (5)
H27A1.34230.81061.04860.028*0.825 (5)
H27B1.31520.87881.11130.028*0.825 (5)
C28A1.3991 (2)0.7212 (4)1.1505 (2)0.0314 (9)0.825 (5)
H28A1.38280.70071.19330.038*0.825 (5)
H28B1.41040.63381.13070.038*0.825 (5)
C29A1.4787 (2)0.8059 (4)1.1757 (2)0.0314 (9)0.825 (5)
H29A1.52090.75111.21100.038*0.825 (5)
H29B1.49650.82151.13330.038*0.825 (5)
C30A1.47384 (19)0.9447 (4)1.2109 (2)0.0253 (8)0.825 (5)
H30A1.43891.00631.17270.030*0.825 (5)
C31A1.4363 (3)0.9328 (5)1.2731 (3)0.0296 (10)0.825 (5)
H31A1.38000.90341.25290.044*0.825 (5)
H31B1.43861.02111.29660.044*0.825 (5)
H31C1.46690.86631.30890.044*0.825 (5)
C32A1.5599 (2)1.0087 (5)1.2413 (3)0.0410 (11)0.825 (5)
H32A1.58371.01491.20250.062*0.825 (5)
H32B1.59420.95181.28050.062*0.825 (5)
H32C1.55591.09961.26000.062*0.825 (5)
C27X1.3244 (12)0.728 (2)1.0891 (12)0.025 (5)*0.175 (5)
H27C1.34610.70831.04930.030*0.175 (5)
H27D1.35380.67161.13130.030*0.175 (5)
C28X1.3364 (11)0.880 (2)1.1096 (11)0.032 (4)*0.175 (5)
H28C1.30940.90061.14560.038*0.175 (5)
H28D1.31040.93551.06590.038*0.175 (5)
C29X1.4293 (9)0.9195 (18)1.1422 (9)0.028 (4)*0.175 (5)
H29C1.45680.88901.10800.033*0.175 (5)
H29F1.43351.01941.14530.033*0.175 (5)
C30X1.4744 (9)0.860 (2)1.2173 (11)0.036 (4)*0.175 (5)
H30B1.45660.76581.22280.043*0.175 (5)
C31X1.4547 (17)0.961 (3)1.2710 (16)0.036 (4)*0.175 (5)
H31D1.49030.94301.32040.054*0.175 (5)
H31E1.39830.95001.26850.054*0.175 (5)
H31F1.46321.05451.25760.054*0.175 (5)
C32X1.5679 (10)0.870 (3)1.2335 (13)0.052 (6)*0.175 (5)
H32D1.58250.82151.19580.077*0.175 (5)
H32E1.59590.82851.28070.077*0.175 (5)
H32F1.58380.96501.23420.077*0.175 (5)
O1B1.40344 (10)0.9093 (2)0.44593 (10)0.0257 (4)
O2B1.39603 (14)1.1422 (3)0.44671 (13)0.0406 (6)
O3B1.06940 (10)0.8041 (2)0.66162 (10)0.0235 (4)
N1B1.13933 (12)0.8916 (2)0.51634 (12)0.0179 (4)
N2B1.08365 (13)0.8767 (2)0.55456 (12)0.0191 (5)
N3B1.27080 (15)0.6266 (3)0.60085 (14)0.0314 (6)
C1B1.02418 (14)0.9475 (3)0.39848 (14)0.0174 (5)
H1BA1.02081.03640.37420.021*
H1BB0.98830.95000.42840.021*
C2B1.11173 (14)0.9215 (3)0.44725 (14)0.0160 (5)
C3B1.17228 (14)0.9097 (3)0.40589 (13)0.0156 (5)
H3BA1.16240.98820.37170.019*
C4B1.26343 (14)0.9150 (3)0.45409 (14)0.0194 (5)
H4BA1.27531.00160.48100.023*
H4BB1.27590.83970.48960.023*
C5B1.31564 (14)0.9021 (3)0.40366 (14)0.0200 (5)
H5BA1.30140.97690.36710.024*
C6B1.30073 (15)0.7643 (3)0.36409 (15)0.0220 (6)
H6BA1.31360.68960.39990.026*
H6BB1.33600.75550.33380.026*
C7B1.20998 (14)0.7558 (3)0.31530 (14)0.0188 (5)
H7BA1.20020.66640.29100.023*
H7BB1.19950.82600.27710.023*
C8B1.14854 (14)0.7754 (3)0.35791 (13)0.0161 (5)
C9B1.06048 (14)0.7990 (3)0.30241 (13)0.0167 (5)
H9BA1.06390.88090.27340.020*
C10B1.02858 (15)0.6814 (3)0.24687 (14)0.0215 (6)
H10C1.02360.59830.27350.026*
H10D1.06870.66320.22220.026*
C11B0.94502 (15)0.7126 (3)0.18838 (14)0.0207 (5)
H11C0.92670.63180.15730.025*
H11D0.95150.78790.15730.025*
C12B0.87914 (14)0.7520 (3)0.22299 (13)0.0170 (5)
C13B0.80126 (15)0.8260 (3)0.17172 (14)0.0184 (5)
H13B0.82060.89450.14340.022*
C14B0.76889 (16)0.9089 (3)0.22640 (15)0.0239 (6)
H14C0.74880.99890.20590.029*
H14D0.72410.85940.23570.029*
C15B0.84253 (15)0.9252 (3)0.29900 (14)0.0207 (5)
H15C0.85061.02140.31410.025*
H15D0.83410.87120.33860.025*
C16B0.91555 (15)0.8707 (3)0.27870 (14)0.0165 (5)
H16B0.93010.94450.25010.020*
C17B0.99553 (14)0.8327 (3)0.33988 (13)0.0161 (5)
H17B0.98560.74870.36440.019*
C18B1.11377 (15)0.8330 (3)0.62498 (14)0.0190 (5)
C19B1.20771 (15)0.8238 (3)0.65905 (14)0.0224 (6)
H19C1.23170.91180.65270.027*
H19D1.22220.80660.71170.027*
C20B1.24303 (15)0.7139 (3)0.62561 (15)0.0227 (6)
C21B1.43596 (18)1.0379 (4)0.46018 (16)0.0311 (7)
C22B1.52840 (17)1.0310 (5)0.49423 (19)0.0457 (9)
H22D1.54611.09190.53610.069*
H22E1.55341.05870.45840.069*
H22F1.54460.93800.50990.069*
C23B1.15183 (16)0.6469 (3)0.40651 (15)0.0205 (5)
H23D1.14800.56480.37740.031*
H23E1.10660.64960.42550.031*
H23F1.20290.64630.44690.031*
C24B0.85473 (16)0.6264 (3)0.26037 (15)0.0223 (6)
H24D0.83160.55610.22400.033*
H24E0.81470.65400.28280.033*
H24F0.90270.59060.29770.033*
C25B0.76610 (17)0.6444 (3)0.06897 (16)0.0282 (6)
H25D0.72110.59760.03330.042*
H25E0.80190.57760.10090.042*
H25F0.79640.69650.04380.042*
C26B0.73254 (15)0.7424 (3)0.11504 (14)0.0207 (5)
H26A0.70430.68680.14220.025*
C27B0.66974 (17)0.8419 (3)0.06442 (15)0.0275 (6)
H27E0.65010.90300.09520.033*
H27F0.69810.89870.03860.033*
C28B0.59475 (16)0.7767 (3)0.00684 (15)0.0266 (6)
H28E0.61350.7164−0.02490.032*
H28F0.56550.72030.03200.032*
C29B0.5358 (2)0.8828 (4)−0.04063 (18)0.0420 (8)
H29D0.56790.9517−0.05610.050*
H29E0.50850.9294−0.01020.050*
C30B0.46996 (18)0.8271 (4)−0.10934 (17)0.0366 (8)
H30C0.49620.7974−0.14520.044*0.630 (18)
H30D0.49580.7573−0.13170.044*0.370 (18)
C31B0.4227 (4)0.7039 (9)−0.0914 (5)0.0376 (18)0.630 (18)
H31G0.45820.6246−0.07920.056*0.630 (18)
H31H0.37540.6834−0.13370.056*0.630 (18)
H31I0.40500.7272−0.05020.056*0.630 (18)
C32B0.4050 (5)0.9398 (7)−0.1451 (5)0.047 (2)0.630 (18)
H32G0.37180.9566−0.11420.071*0.630 (18)
H32H0.37040.9090−0.19290.071*0.630 (18)
H32I0.43251.0237−0.15040.071*0.630 (18)
C31Y0.4060 (8)0.757 (2)−0.0858 (9)0.058 (4)0.370 (18)
H31J0.42930.6769−0.05710.087*0.370 (18)
H31K0.36110.7298−0.12870.087*0.370 (18)
H31L0.38610.8195−0.05650.087*0.370 (18)
C32Y0.4369 (10)0.9435 (11)−0.1666 (6)0.046 (3)0.370 (18)
H32J0.48120.9801−0.18110.069*0.370 (18)
H32K0.41391.0158−0.14500.069*0.370 (18)
H32L0.39500.9070−0.20920.069*0.370 (18)
H1NA0.9409 (19)0.794 (4)0.6297 (18)0.033 (9)*
H1NB1.0301 (17)0.870 (3)0.5324 (15)0.021 (8)*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O1A0.0151 (8)0.0312 (12)0.0318 (11)−0.0025 (8)0.0047 (8)−0.0029 (9)
O2A0.0431 (13)0.0400 (15)0.0440 (14)−0.0065 (11)0.0025 (12)0.0057 (12)
O3A0.0203 (9)0.0361 (12)0.0181 (9)−0.0048 (9)0.0068 (8)−0.0006 (9)
N1A0.0180 (10)0.0165 (11)0.0186 (10)−0.0001 (9)0.0080 (9)0.0010 (9)
N2A0.0147 (10)0.0229 (12)0.0162 (10)0.0020 (9)0.0044 (9)0.0021 (9)
N3A0.0277 (13)0.0465 (17)0.0246 (13)−0.0109 (12)0.0087 (11)−0.0060 (12)
C1A0.0172 (11)0.0268 (15)0.0193 (12)−0.0016 (11)0.0067 (10)0.0043 (12)
C2A0.0177 (11)0.0134 (12)0.0197 (12)−0.0006 (10)0.0083 (10)0.0004 (10)
C3A0.0197 (12)0.0169 (13)0.0173 (12)−0.0024 (10)0.0079 (10)−0.0029 (10)
C4A0.0182 (11)0.0226 (14)0.0236 (13)−0.0022 (11)0.0082 (11)−0.0015 (12)
C5A0.0152 (11)0.0277 (15)0.0261 (14)−0.0041 (11)0.0066 (11)−0.0044 (12)
C6A0.0181 (12)0.0397 (18)0.0266 (14)−0.0045 (12)0.0121 (11)−0.0047 (13)
C7A0.0195 (12)0.0360 (17)0.0182 (12)−0.0028 (12)0.0080 (11)−0.0022 (12)
C8A0.0172 (11)0.0188 (13)0.0154 (11)−0.0013 (10)0.0071 (10)−0.0018 (10)
C9A0.0182 (11)0.0141 (13)0.0155 (11)−0.0010 (10)0.0066 (10)0.0008 (10)
C10A0.0199 (12)0.0248 (14)0.0167 (12)−0.0004 (11)0.0089 (10)0.0019 (11)
C11A0.0212 (12)0.0220 (14)0.0174 (12)0.0036 (11)0.0069 (10)0.0002 (11)
C12A0.0205 (12)0.0190 (13)0.0129 (11)0.0012 (10)0.0080 (10)0.0000 (10)
C13A0.0169 (11)0.0231 (14)0.0164 (12)0.0026 (10)0.0039 (10)−0.0004 (11)
C14A0.0197 (12)0.0229 (14)0.0170 (12)0.0025 (10)0.0075 (10)0.0019 (11)
C15A0.0186 (12)0.0249 (14)0.0178 (12)−0.0010 (11)0.0085 (10)0.0024 (11)
C16A0.0157 (11)0.0171 (13)0.0173 (12)−0.0006 (10)0.0058 (10)0.0004 (10)
C17A0.0201 (12)0.0154 (13)0.0152 (11)0.0005 (10)0.0075 (10)0.0021 (10)
C18A0.0168 (11)0.0181 (13)0.0187 (12)−0.0032 (10)0.0041 (10)0.0000 (11)
C19A0.0178 (11)0.0285 (15)0.0158 (12)−0.0018 (11)0.0030 (10)−0.0011 (12)
C20A0.0205 (12)0.0287 (16)0.0199 (13)−0.0048 (11)0.0073 (11)0.0012 (12)
C21A0.0272 (15)0.0384 (19)0.0252 (15)−0.0001 (14)0.0071 (13)0.0005 (14)
C22A0.0245 (14)0.055 (2)0.0349 (17)−0.0022 (15)0.0001 (14)0.0073 (17)
C23A0.0253 (13)0.0203 (14)0.0234 (14)−0.0062 (11)0.0059 (12)0.0012 (11)
C24A0.0249 (13)0.0212 (14)0.0212 (13)0.0027 (11)0.0091 (11)0.0048 (11)
C25A0.0260 (13)0.0307 (16)0.0165 (12)0.0054 (12)0.0055 (11)−0.0010 (12)
C26A0.0251 (13)0.0298 (15)0.0168 (12)0.0075 (12)0.0056 (11)0.0006 (12)
C27A0.0205 (16)0.027 (3)0.0222 (18)0.0008 (16)0.0065 (13)−0.0025 (18)
C28A0.0248 (17)0.033 (2)0.0283 (18)0.0029 (15)−0.0024 (15)−0.0046 (17)
C29A0.0191 (15)0.043 (2)0.0286 (18)0.0039 (16)0.0026 (14)−0.0092 (18)
C30A0.0147 (15)0.030 (2)0.0276 (19)−0.0003 (14)0.0027 (14)0.0022 (16)
C31A0.033 (2)0.036 (3)0.0245 (19)−0.0042 (19)0.0158 (18)−0.0008 (18)
C32A0.0228 (19)0.045 (3)0.050 (3)−0.0071 (17)0.0039 (19)−0.006 (2)
O1B0.0156 (8)0.0364 (12)0.0234 (10)−0.0023 (8)0.0040 (8)−0.0004 (9)
O2B0.0367 (12)0.0372 (14)0.0402 (13)−0.0090 (11)0.0021 (10)0.0019 (12)
O3B0.0203 (9)0.0351 (11)0.0161 (9)−0.0058 (8)0.0073 (7)0.0002 (9)
N1B0.0170 (10)0.0216 (12)0.0166 (10)−0.0003 (9)0.0078 (9)−0.0024 (9)
N2B0.0143 (10)0.0299 (13)0.0140 (10)0.0007 (9)0.0059 (9)−0.0004 (9)
N3B0.0278 (13)0.0344 (15)0.0303 (13)0.0050 (11)0.0072 (11)0.0059 (12)
C1B0.0175 (12)0.0191 (13)0.0168 (12)0.0024 (10)0.0073 (10)−0.0013 (11)
C2B0.0139 (11)0.0148 (13)0.0181 (12)−0.0003 (10)0.0037 (10)−0.0018 (10)
C3B0.0166 (11)0.0168 (13)0.0137 (11)0.0013 (10)0.0052 (10)0.0019 (10)
C4B0.0194 (12)0.0218 (14)0.0177 (12)−0.0009 (11)0.0069 (10)0.0003 (11)
C5B0.0147 (11)0.0268 (15)0.0180 (12)0.0014 (11)0.0045 (10)0.0023 (11)
C6B0.0186 (12)0.0290 (15)0.0201 (12)0.0024 (11)0.0087 (10)−0.0009 (12)
C7B0.0187 (11)0.0215 (14)0.0174 (12)0.0033 (10)0.0077 (10)0.0001 (11)
C8B0.0173 (11)0.0173 (13)0.0144 (11)0.0020 (10)0.0060 (10)0.0002 (10)
C9B0.0179 (11)0.0166 (13)0.0163 (11)0.0027 (10)0.0066 (10)0.0011 (10)
C10B0.0207 (13)0.0241 (15)0.0203 (13)0.0013 (11)0.0078 (11)−0.0034 (11)
C11B0.0213 (12)0.0245 (14)0.0166 (12)−0.0007 (11)0.0066 (10)−0.0045 (11)
C12B0.0173 (11)0.0186 (13)0.0151 (11)0.0010 (10)0.0055 (10)0.0013 (10)
C13B0.0177 (11)0.0205 (14)0.0162 (12)−0.0009 (10)0.0043 (10)0.0026 (11)
C14B0.0216 (12)0.0268 (15)0.0224 (13)0.0016 (11)0.0058 (11)−0.0019 (12)
C15B0.0198 (12)0.0230 (14)0.0176 (12)0.0022 (11)0.0039 (10)−0.0034 (11)
C16B0.0174 (11)0.0175 (13)0.0151 (11)0.0019 (10)0.0062 (10)0.0020 (10)
C17B0.0172 (11)0.0159 (13)0.0152 (11)−0.0007 (10)0.0051 (10)0.0007 (10)
C18B0.0178 (11)0.0217 (14)0.0179 (12)−0.0033 (10)0.0065 (10)−0.0028 (11)
C19B0.0176 (12)0.0314 (16)0.0169 (12)−0.0016 (11)0.0039 (10)0.0000 (12)
C20B0.0161 (12)0.0283 (16)0.0226 (13)−0.0009 (11)0.0048 (11)0.0060 (12)
C21B0.0245 (14)0.045 (2)0.0233 (15)−0.0070 (14)0.0071 (12)0.0002 (15)
C22B0.0243 (15)0.072 (3)0.0375 (19)−0.0131 (17)0.0057 (15)−0.0032 (19)
C23B0.0226 (13)0.0163 (13)0.0207 (13)0.0013 (11)0.0045 (11)−0.0005 (11)
C24B0.0252 (13)0.0209 (14)0.0193 (13)−0.0020 (11)0.0052 (11)0.0027 (11)
C25B0.0274 (14)0.0322 (17)0.0218 (14)−0.0024 (13)0.0037 (12)−0.0058 (13)
C26B0.0212 (12)0.0223 (14)0.0172 (12)−0.0040 (11)0.0042 (10)−0.0005 (11)
C27B0.0247 (13)0.0301 (16)0.0227 (14)−0.0006 (12)0.0009 (12)−0.0001 (13)
C28B0.0222 (13)0.0321 (17)0.0206 (13)−0.0045 (12)0.0005 (11)−0.0001 (13)
C29B0.0386 (17)0.043 (2)0.0295 (17)0.0080 (16)−0.0087 (14)−0.0026 (16)
C30B0.0268 (14)0.048 (2)0.0270 (15)0.0015 (14)−0.0016 (13)−0.0019 (15)
C31B0.011 (3)0.055 (4)0.043 (4)0.000 (3)0.003 (2)−0.005 (3)
C32B0.029 (3)0.047 (3)0.048 (4)0.001 (3)−0.010 (3)0.004 (3)
C31Y0.019 (5)0.121 (11)0.037 (5)0.010 (6)0.015 (4)0.007 (7)
C32Y0.029 (6)0.071 (6)0.025 (5)0.010 (5)−0.009 (4)−0.007 (4)
Geometric parameters (Å, °)
O1A—C21A1.334 (4)C31X—H31E0.9600
O1A—C5A1.457 (3)C31X—H31F0.9600
O2A—C21A1.209 (4)C32X—H32D0.9600
O3A—C18A1.228 (3)C32X—H32E0.9600
N1A—C2A1.287 (3)C32X—H32F0.9600
N1A—N2A1.394 (3)O1B—C21B1.353 (4)
N2A—C18A1.352 (3)O1B—C5B1.460 (3)
N2A—H1NA0.85 (3)O2B—C21B1.199 (4)
N3A—C20A1.143 (3)O3B—C18B1.225 (3)
C1A—C2A1.506 (3)N1B—C2B1.283 (3)
C1A—C17A1.534 (3)N1B—N2B1.389 (3)
C1A—H1AA0.9700N2B—C18B1.344 (3)
C1A—H1AB0.9700N2B—H1NB0.88 (3)
C2A—C3A1.516 (3)N3B—C20B1.147 (4)
C3A—C4A1.533 (3)C1B—C2B1.508 (3)
C3A—C8A1.554 (4)C1B—C17B1.540 (4)
C3A—H3AA0.9800C1B—H1BA0.9700
C4A—C5A1.524 (3)C1B—H1BB0.9700
C4A—H4AA0.9700C2B—C3B1.504 (3)
C4A—H4AB0.9700C3B—C4B1.534 (3)
C5A—C6A1.506 (4)C3B—C8B1.566 (4)
C5A—H5AA0.9800C3B—H3BA0.9800
C6A—C7A1.540 (3)C4B—C5B1.523 (3)
C6A—H6AA0.9700C4B—H4BA0.9700
C6A—H6AB0.9700C4B—H4BB0.9700
C7A—C8A1.537 (3)C5B—C6B1.512 (4)
C7A—H7AA0.9700C5B—H5BA0.9800
C7A—H7AB0.9700C6B—C7B1.533 (3)
C8A—C23A1.532 (4)C6B—H6BA0.9700
C8A—C9A1.555 (3)C6B—H6BB0.9700
C9A—C10A1.534 (3)C7B—C8B1.543 (3)
C9A—C17A1.539 (3)C7B—H7BA0.9700
C9A—H9AA0.9800C7B—H7BB0.9700
C10A—C11A1.539 (3)C8B—C23B1.542 (4)
C10A—H10A0.9700C8B—C9B1.553 (3)
C10A—H10B0.9700C9B—C10B1.530 (4)
C11A—C12A1.531 (3)C9B—C17B1.546 (3)
C11A—H11A0.9700C9B—H9BA0.9800
C11A—H11B0.9700C10B—C11B1.532 (4)
C12A—C24A1.534 (4)C10B—H10C0.9700
C12A—C16A1.543 (3)C10B—H10D0.9700
C12A—C13A1.562 (3)C11B—C12B1.535 (3)
C13A—C26A1.540 (4)C11B—H11C0.9700
C13A—C14A1.556 (3)C11B—H11D0.9700
C13A—H13A0.9800C12B—C24B1.536 (4)
C14A—C15A1.548 (3)C12B—C13B1.550 (3)
C14A—H14A0.9700C12B—C16B1.552 (4)
C14A—H14B0.9700C13B—C26B1.544 (3)
C15A—C16A1.533 (3)C13B—C14B1.558 (4)
C15A—H15A0.9700C13B—H13B0.9800
C15A—H15B0.9700C14B—C15B1.550 (4)
C16A—C17A1.529 (3)C14B—H14C0.9700
C16A—H16A0.9800C14B—H14D0.9700
C17A—H17A0.9800C15B—C16B1.523 (3)
C18A—C19A1.524 (3)C15B—H15C0.9700
C19A—C20A1.469 (4)C15B—H15D0.9700
C19A—H19A0.9700C16B—C17B1.529 (3)
C19A—H19B0.9700C16B—H16B0.9800
C21A—C22A1.499 (4)C17B—H17B0.9800
C22A—H22A0.9600C18B—C19B1.531 (3)
C22A—H22B0.9600C19B—C20B1.470 (4)
C22A—H22C0.9600C19B—H19C0.9700
C23A—H23A0.9600C19B—H19D0.9700
C23A—H23B0.9600C21B—C22B1.506 (4)
C23A—H23C0.9600C22B—H22D0.9600
C24A—H24A0.9600C22B—H22E0.9600
C24A—H24B0.9600C22B—H22F0.9600
C24A—H24C0.9600C23B—H23D0.9600
C25A—C26A1.537 (4)C23B—H23E0.9600
C25A—H25A0.9600C23B—H23F0.9600
C25A—H25B0.9600C24B—H24D0.9600
C25A—H25C0.9600C24B—H24E0.9600
C26A—C27X1.31 (2)C24B—H24F0.9600
C26A—C27A1.587 (5)C25B—C26B1.530 (4)
C26A—H26B0.9800C25B—H25D0.9600
C26A—H26C0.9800C25B—H25E0.9600
C27A—C28A1.532 (5)C25B—H25F0.9600
C27A—H27A0.9700C26B—C27B1.530 (4)
C27A—H27B0.9700C26B—H26A0.9800
C28A—C29A1.530 (5)C27B—C28B1.529 (4)
C28A—H28A0.9700C27B—H27E0.9700
C28A—H28B0.9700C27B—H27F0.9700
C29A—C30A1.516 (6)C28B—C29B1.516 (4)
C29A—H29A0.9700C28B—H28E0.9700
C29A—H29B0.9700C28B—H28F0.9700
C30A—C32A1.530 (5)C29B—C30B1.524 (4)
C30A—C31A1.534 (5)C29B—H29D0.9700
C30A—H30A0.9800C29B—H29E0.9700
C31A—H31A0.9600C30B—C31Y1.480 (8)
C31A—H31B0.9600C30B—C31B1.542 (8)
C31A—H31C0.9600C30B—C32Y1.543 (8)
C32A—H32A0.9600C30B—C32B1.549 (7)
C32A—H32B0.9600C30B—H30C0.9800
C32A—H32C0.9600C30B—H30D0.9800
C27X—C28X1.52 (3)C31B—H31G0.9600
C27X—H27C0.9700C31B—H31H0.9600
C27X—H27D0.9700C31B—H31I0.9600
C28X—C29X1.56 (2)C32B—H32G0.9600
C28X—H28C0.9700C32B—H32H0.9600
C28X—H28D0.9700C32B—H32I0.9600
C29X—C30X1.50 (3)C31Y—H31J0.9600
C29X—H29C0.9700C31Y—H31K0.9600
C29X—H29F0.9700C31Y—H31L0.9600
C30X—C32X1.534 (10)C32Y—H32J0.9600
C30X—C31X1.535 (10)C32Y—H32K0.9600
C30X—H30B0.9800C32Y—H32L0.9600
C31X—H31D0.9600
C21A—O1A—C5A117.7 (2)C30X—C31X—H31F109.5
C2A—N1A—N2A118.00 (19)H31D—C31X—H31F109.5
C18A—N2A—N1A120.3 (2)H31E—C31X—H31F109.5
C18A—N2A—H1NA117 (2)C30X—C32X—H32D109.5
N1A—N2A—H1NA122 (2)C30X—C32X—H32E109.5
C2A—C1A—C17A115.6 (2)H32D—C32X—H32E109.5
C2A—C1A—H1AA108.4C30X—C32X—H32F109.5
C17A—C1A—H1AA108.4H32D—C32X—H32F109.5
C2A—C1A—H1AB108.4H32E—C32X—H32F109.5
C17A—C1A—H1AB108.4C21B—O1B—C5B116.0 (2)
H1AA—C1A—H1AB107.4C2B—N1B—N2B118.8 (2)
N1A—C2A—C1A126.3 (2)C18B—N2B—N1B117.2 (2)
N1A—C2A—C3A116.4 (2)C18B—N2B—H1NB117.1 (19)
C1A—C2A—C3A117.0 (2)N1B—N2B—H1NB123.1 (18)
C2A—C3A—C4A114.2 (2)C2B—C1B—C17B110.2 (2)
C2A—C3A—C8A111.7 (2)C2B—C1B—H1BA109.6
C4A—C3A—C8A113.2 (2)C17B—C1B—H1BA109.6
C2A—C3A—H3AA105.6C2B—C1B—H1BB109.6
C4A—C3A—H3AA105.6C17B—C1B—H1BB109.6
C8A—C3A—H3AA105.6H1BA—C1B—H1BB108.1
C5A—C4A—C3A110.0 (2)N1B—C2B—C3B116.1 (2)
C5A—C4A—H4AA109.7N1B—C2B—C1B129.2 (2)
C3A—C4A—H4AA109.7C3B—C2B—C1B114.1 (2)
C5A—C4A—H4AB109.7C2B—C3B—C4B115.2 (2)
C3A—C4A—H4AB109.7C2B—C3B—C8B106.25 (19)
H4AA—C4A—H4AB108.2C4B—C3B—C8B113.4 (2)
O1A—C5A—C6A105.8 (2)C2B—C3B—H3BA107.2
O1A—C5A—C4A109.8 (2)C4B—C3B—H3BA107.2
C6A—C5A—C4A112.4 (2)C8B—C3B—H3BA107.2
O1A—C5A—H5AA109.6C5B—C4B—C3B108.2 (2)
C6A—C5A—H5AA109.6C5B—C4B—H4BA110.1
C4A—C5A—H5AA109.6C3B—C4B—H4BA110.1
C5A—C6A—C7A110.8 (2)C5B—C4B—H4BB110.1
C5A—C6A—H6AA109.5C3B—C4B—H4BB110.1
C7A—C6A—H6AA109.5H4BA—C4B—H4BB108.4
C5A—C6A—H6AB109.5O1B—C5B—C6B107.1 (2)
C7A—C6A—H6AB109.5O1B—C5B—C4B111.1 (2)
H6AA—C6A—H6AB108.1C6B—C5B—C4B110.6 (2)
C8A—C7A—C6A113.9 (2)O1B—C5B—H5BA109.3
C8A—C7A—H7AA108.8C6B—C5B—H5BA109.3
C6A—C7A—H7AA108.8C4B—C5B—H5BA109.3
C8A—C7A—H7AB108.8C5B—C6B—C7B108.9 (2)
C6A—C7A—H7AB108.8C5B—C6B—H6BA109.9
H7AA—C7A—H7AB107.7C7B—C6B—H6BA109.9
C23A—C8A—C7A110.1 (2)C5B—C6B—H6BB109.9
C23A—C8A—C3A110.5 (2)C7B—C6B—H6BB109.9
C7A—C8A—C3A108.3 (2)H6BA—C6B—H6BB108.3
C23A—C8A—C9A110.9 (2)C6B—C7B—C8B113.9 (2)
C7A—C8A—C9A109.6 (2)C6B—C7B—H7BA108.8
C3A—C8A—C9A107.42 (19)C8B—C7B—H7BA108.8
C10A—C9A—C17A111.78 (19)C6B—C7B—H7BB108.8
C10A—C9A—C8A114.92 (19)C8B—C7B—H7BB108.8
C17A—C9A—C8A111.30 (19)H7BA—C7B—H7BB107.7
C10A—C9A—H9AA106.0C23B—C8B—C7B108.9 (2)
C17A—C9A—H9AA106.0C23B—C8B—C9B111.5 (2)
C8A—C9A—H9AA106.0C7B—C8B—C9B109.72 (19)
C9A—C10A—C11A112.8 (2)C23B—C8B—C3B111.31 (19)
C9A—C10A—H10A109.0C7B—C8B—C3B108.70 (19)
C11A—C10A—H10A109.0C9B—C8B—C3B106.66 (19)
C9A—C10A—H10B109.0C10B—C9B—C17B109.3 (2)
C11A—C10A—H10B109.0C10B—C9B—C8B114.3 (2)
H10A—C10A—H10B107.8C17B—C9B—C8B113.71 (19)
C12A—C11A—C10A112.2 (2)C10B—C9B—H9BA106.3
C12A—C11A—H11A109.2C17B—C9B—H9BA106.3
C10A—C11A—H11A109.2C8B—C9B—H9BA106.3
C12A—C11A—H11B109.2C9B—C10B—C11B113.4 (2)
C10A—C11A—H11B109.2C9B—C10B—H10C108.9
H11A—C11A—H11B107.9C11B—C10B—H10C108.9
C11A—C12A—C24A110.4 (2)C9B—C10B—H10D108.9
C11A—C12A—C16A107.0 (2)C11B—C10B—H10D108.9
C24A—C12A—C16A112.3 (2)H10C—C10B—H10D107.7
C11A—C12A—C13A117.3 (2)C10B—C11B—C12B112.3 (2)
C24A—C12A—C13A109.7 (2)C10B—C11B—H11C109.1
C16A—C12A—C13A99.55 (19)C12B—C11B—H11C109.1
C26A—C13A—C14A112.0 (2)C10B—C11B—H11D109.1
C26A—C13A—C12A119.6 (2)C12B—C11B—H11D109.1
C14A—C13A—C12A102.96 (19)H11C—C11B—H11D107.9
C26A—C13A—H13A107.2C11B—C12B—C24B110.9 (2)
C14A—C13A—H13A107.2C11B—C12B—C13B116.5 (2)
C12A—C13A—H13A107.2C24B—C12B—C13B110.5 (2)
C15A—C14A—C13A107.14 (18)C11B—C12B—C16B107.02 (19)
C15A—C14A—H14A110.3C24B—C12B—C16B112.0 (2)
C13A—C14A—H14A110.3C13B—C12B—C16B99.36 (19)
C15A—C14A—H14B110.3C26B—C13B—C12B120.3 (2)
C13A—C14A—H14B110.3C26B—C13B—C14B112.5 (2)
H14A—C14A—H14B108.5C12B—C13B—C14B103.64 (19)
C16A—C15A—C14A103.45 (19)C26B—C13B—H13B106.5
C16A—C15A—H15A111.1C12B—C13B—H13B106.5
C14A—C15A—H15A111.1C14B—C13B—H13B106.5
C16A—C15A—H15B111.1C15B—C14B—C13B106.8 (2)
C14A—C15A—H15B111.1C15B—C14B—H14C110.4
H15A—C15A—H15B109.0C13B—C14B—H14C110.4
C17A—C16A—C15A118.5 (2)C15B—C14B—H14D110.4
C17A—C16A—C12A114.6 (2)C13B—C14B—H14D110.4
C15A—C16A—C12A104.39 (19)H14C—C14B—H14D108.6
C17A—C16A—H16A106.2C16B—C15B—C14B103.5 (2)
C15A—C16A—H16A106.2C16B—C15B—H15C111.1
C12A—C16A—H16A106.2C14B—C15B—H15C111.1
C16A—C17A—C1A110.6 (2)C16B—C15B—H15D111.1
C16A—C17A—C9A109.15 (19)C14B—C15B—H15D111.1
C1A—C17A—C9A111.6 (2)H15C—C15B—H15D109.0
C16A—C17A—H17A108.5C15B—C16B—C17B119.7 (2)
C1A—C17A—H17A108.5C15B—C16B—C12B104.58 (19)
C9A—C17A—H17A108.5C17B—C16B—C12B114.0 (2)
O3A—C18A—N2A121.0 (2)C15B—C16B—H16B105.9
O3A—C18A—C19A121.8 (2)C17B—C16B—H16B105.9
N2A—C18A—C19A117.2 (2)C12B—C16B—H16B105.9
C20A—C19A—C18A110.7 (2)C16B—C17B—C1B112.1 (2)
C20A—C19A—H19A109.5C16B—C17B—C9B107.37 (19)
C18A—C19A—H19A109.5C1B—C17B—C9B112.54 (19)
C20A—C19A—H19B109.5C16B—C17B—H17B108.2
C18A—C19A—H19B109.5C1B—C17B—H17B108.2
H19A—C19A—H19B108.1C9B—C17B—H17B108.2
N3A—C20A—C19A177.9 (3)O3B—C18B—N2B122.6 (2)
O2A—C21A—O1A123.7 (3)O3B—C18B—C19B120.6 (2)
O2A—C21A—C22A125.3 (3)N2B—C18B—C19B116.7 (2)
O1A—C21A—C22A111.0 (3)C20B—C19B—C18B112.6 (2)
C21A—C22A—H22A109.5C20B—C19B—H19C109.1
C21A—C22A—H22B109.5C18B—C19B—H19C109.1
H22A—C22A—H22B109.5C20B—C19B—H19D109.1
C21A—C22A—H22C109.5C18B—C19B—H19D109.1
H22A—C22A—H22C109.5H19C—C19B—H19D107.8
H22B—C22A—H22C109.5N3B—C20B—C19B178.5 (3)
C8A—C23A—H23A109.5O2B—C21B—O1B124.1 (3)
C8A—C23A—H23B109.5O2B—C21B—C22B125.3 (3)
H23A—C23A—H23B109.5O1B—C21B—C22B110.7 (3)
C8A—C23A—H23C109.5C21B—C22B—H22D109.5
H23A—C23A—H23C109.5C21B—C22B—H22E109.5
H23B—C23A—H23C109.5H22D—C22B—H22E109.5
C12A—C24A—H24A109.5C21B—C22B—H22F109.5
C12A—C24A—H24B109.5H22D—C22B—H22F109.5
H24A—C24A—H24B109.5H22E—C22B—H22F109.5
C12A—C24A—H24C109.5C8B—C23B—H23D109.5
H24A—C24A—H24C109.5C8B—C23B—H23E109.5
H24B—C24A—H24C109.5H23D—C23B—H23E109.5
C26A—C25A—H25A109.5C8B—C23B—H23F109.5
C26A—C25A—H25B109.5H23D—C23B—H23F109.5
H25A—C25A—H25B109.5H23E—C23B—H23F109.5
C26A—C25A—H25C109.5C12B—C24B—H24D109.5
H25A—C25A—H25C109.5C12B—C24B—H24E109.5
H25B—C25A—H25C109.5H24D—C24B—H24E109.5
C27X—C26A—C25A112.8 (9)C12B—C24B—H24F109.5
C27X—C26A—C13A122.6 (10)H24D—C24B—H24F109.5
C25A—C26A—C13A113.1 (2)H24E—C24B—H24F109.5
C25A—C26A—C27A108.9 (2)C26B—C25B—H25D109.5
C13A—C26A—C27A109.1 (3)C26B—C25B—H25E109.5
C27X—C26A—H26B87.3H25D—C25B—H25E109.5
C25A—C26A—H26B108.5C26B—C25B—H25F109.5
C13A—C26A—H26B108.5H25D—C25B—H25F109.5
C27A—C26A—H26B108.5H25E—C25B—H25F109.5
C27X—C26A—H26C101.4C25B—C26B—C27B110.2 (2)
C25A—C26A—H26C101.4C25B—C26B—C13B112.6 (2)
C13A—C26A—H26C101.4C27B—C26B—C13B109.4 (2)
C27A—C26A—H26C122.7C25B—C26B—H26A108.2
C28A—C27A—C26A113.1 (3)C27B—C26B—H26A108.2
C28A—C27A—H27A109.0C13B—C26B—H26A108.2
C26A—C27A—H27A109.0C28B—C27B—C26B116.6 (2)
C28A—C27A—H27B109.0C28B—C27B—H27E108.1
C26A—C27A—H27B109.0C26B—C27B—H27E108.1
H27A—C27A—H27B107.8C28B—C27B—H27F108.1
C29A—C28A—C27A114.9 (3)C26B—C27B—H27F108.1
C29A—C28A—H28A108.5H27E—C27B—H27F107.3
C27A—C28A—H28A108.5C29B—C28B—C27B113.0 (3)
C29A—C28A—H28B108.5C29B—C28B—H28E109.0
C27A—C28A—H28B108.5C27B—C28B—H28E109.0
H28A—C28A—H28B107.5C29B—C28B—H28F109.0
C30A—C29A—C28A116.2 (3)C27B—C28B—H28F109.0
C30A—C29A—H29A108.2H28E—C28B—H28F107.8
C28A—C29A—H29A108.2C28B—C29B—C30B116.0 (3)
C30A—C29A—H29B108.2C28B—C29B—H29D108.3
C28A—C29A—H29B108.2C30B—C29B—H29D108.3
H29A—C29A—H29B107.4C28B—C29B—H29E108.3
C29A—C30A—C32A109.9 (3)C30B—C29B—H29E108.3
C29A—C30A—C31A112.1 (4)H29D—C29B—H29E107.4
C32A—C30A—C31A109.5 (3)C31Y—C30B—C29B108.3 (7)
C29A—C30A—H30A108.4C29B—C30B—C31B112.1 (4)
C32A—C30A—H30A108.4C31Y—C30B—C32Y114.4 (7)
C31A—C30A—H30A108.4C29B—C30B—C32Y110.5 (5)
C26A—C27X—C28X108.6 (16)C29B—C30B—C32B110.8 (4)
C26A—C27X—H27C110.0C31B—C30B—C32B106.6 (4)
C28X—C27X—H27C110.0C29B—C30B—H30C109.1
C26A—C27X—H27D110.0C31B—C30B—H30C109.1
C28X—C27X—H27D110.0C32B—C30B—H30C109.1
H27C—C27X—H27D108.4C31Y—C30B—H30D107.8
C27X—C28X—C29X112.0 (16)C29B—C30B—H30D107.8
C27X—C28X—H28C109.2C32Y—C30B—H30D107.8
C29X—C28X—H28C109.2C30B—C31B—H31G109.5
C27X—C28X—H28D109.2C30B—C31B—H31H109.5
C29X—C28X—H28D109.2C30B—C31B—H31I109.5
H28C—C28X—H28D107.9C30B—C32B—H32G109.5
C30X—C29X—C28X115.4 (14)C30B—C32B—H32H109.5
C30X—C29X—H29C108.4C30B—C32B—H32I109.5
C28X—C29X—H29C108.4C30B—C31Y—H31J109.5
C30X—C29X—H29F108.4C30B—C31Y—H31K109.5
C28X—C29X—H29F108.4H31J—C31Y—H31K109.5
H29C—C29X—H29F107.5C30B—C31Y—H31L109.5
C29X—C30X—C32X110.3 (17)H31J—C31Y—H31L109.5
C29X—C30X—C31X103.9 (19)H31K—C31Y—H31L109.5
C32X—C30X—C31X105.8 (18)C30B—C32Y—H32J109.5
C29X—C30X—H30B112.1C30B—C32Y—H32K109.5
C32X—C30X—H30B112.1H32J—C32Y—H32K109.5
C31X—C30X—H30B112.1C30B—C32Y—H32L109.5
C30X—C31X—H31D109.5H32J—C32Y—H32L109.5
C30X—C31X—H31E109.5H32K—C32Y—H32L109.5
H31D—C31X—H31E109.5
C2A—N1A—N2A—C18A−173.8 (2)C26A—C27X—C28X—C29X174.8 (14)
N2A—N1A—C2A—C1A−0.4 (4)C27X—C28X—C29X—C30X−69 (2)
N2A—N1A—C2A—C3A173.6 (2)C28X—C29X—C30X—C32X163.5 (17)
C17A—C1A—C2A—N1A−147.5 (3)C28X—C29X—C30X—C31X−83 (2)
C17A—C1A—C2A—C3A38.5 (3)C2B—N1B—N2B—C18B174.0 (2)
N1A—C2A—C3A—C4A8.8 (3)N2B—N1B—C2B—C3B−168.8 (2)
C1A—C2A—C3A—C4A−176.6 (2)N2B—N1B—C2B—C1B1.5 (4)
N1A—C2A—C3A—C8A138.9 (2)C17B—C1B—C2B—N1B−113.6 (3)
C1A—C2A—C3A—C8A−46.5 (3)C17B—C1B—C2B—C3B56.9 (3)
C2A—C3A—C4A—C5A−174.4 (2)N1B—C2B—C3B—C4B−20.9 (3)
C8A—C3A—C4A—C5A56.3 (3)C1B—C2B—C3B—C4B167.3 (2)
C21A—O1A—C5A—C6A142.9 (2)N1B—C2B—C3B—C8B105.6 (2)
C21A—O1A—C5A—C4A−95.6 (3)C1B—C2B—C3B—C8B−66.2 (3)
C3A—C4A—C5A—O1A−173.8 (2)C2B—C3B—C4B—C5B−179.9 (2)
C3A—C4A—C5A—C6A−56.3 (3)C8B—C3B—C4B—C5B57.4 (3)
O1A—C5A—C6A—C7A175.0 (2)C21B—O1B—C5B—C6B154.0 (2)
C4A—C5A—C6A—C7A55.2 (3)C21B—O1B—C5B—C4B−85.2 (3)
C5A—C6A—C7A—C8A−54.5 (3)C3B—C4B—C5B—O1B178.8 (2)
C6A—C7A—C8A—C23A−68.2 (3)C3B—C4B—C5B—C6B−62.4 (3)
C6A—C7A—C8A—C3A52.7 (3)O1B—C5B—C6B—C7B−176.7 (2)
C6A—C7A—C8A—C9A169.6 (2)C4B—C5B—C6B—C7B62.1 (3)
C2A—C3A—C8A—C23A−63.9 (3)C5B—C6B—C7B—C8B−56.9 (3)
C4A—C3A—C8A—C23A66.7 (3)C6B—C7B—C8B—C23B−70.8 (3)
C2A—C3A—C8A—C7A175.4 (2)C6B—C7B—C8B—C9B166.9 (2)
C4A—C3A—C8A—C7A−54.0 (3)C6B—C7B—C8B—C3B50.6 (3)
C2A—C3A—C8A—C9A57.2 (3)C2B—C3B—C8B—C23B−58.8 (2)
C4A—C3A—C8A—C9A−172.2 (2)C4B—C3B—C8B—C23B68.8 (3)
C23A—C8A—C9A—C10A−70.4 (3)C2B—C3B—C8B—C7B−178.74 (19)
C7A—C8A—C9A—C10A51.3 (3)C4B—C3B—C8B—C7B−51.2 (3)
C3A—C8A—C9A—C10A168.7 (2)C2B—C3B—C8B—C9B63.0 (2)
C23A—C8A—C9A—C17A57.9 (3)C4B—C3B—C8B—C9B−169.40 (19)
C7A—C8A—C9A—C17A179.6 (2)C23B—C8B—C9B—C10B−62.1 (3)
C3A—C8A—C9A—C17A−63.0 (3)C7B—C8B—C9B—C10B58.6 (3)
C17A—C9A—C10A—C11A52.4 (3)C3B—C8B—C9B—C10B176.2 (2)
C8A—C9A—C10A—C11A−179.5 (2)C23B—C8B—C9B—C17B64.4 (3)
C9A—C10A—C11A—C12A−55.0 (3)C7B—C8B—C9B—C17B−174.9 (2)
C10A—C11A—C12A—C24A−67.1 (3)C3B—C8B—C9B—C17B−57.3 (3)
C10A—C11A—C12A—C16A55.5 (3)C17B—C9B—C10B—C11B56.4 (3)
C10A—C11A—C12A—C13A166.2 (2)C8B—C9B—C10B—C11B−174.8 (2)
C11A—C12A—C13A—C26A78.7 (3)C9B—C10B—C11B—C12B−54.9 (3)
C24A—C12A—C13A—C26A−48.4 (3)C10B—C11B—C12B—C24B−69.8 (3)
C16A—C12A—C13A—C26A−166.4 (2)C10B—C11B—C12B—C13B162.7 (2)
C11A—C12A—C13A—C14A−156.4 (2)C10B—C11B—C12B—C16B52.7 (3)
C24A—C12A—C13A—C14A76.6 (2)C11B—C12B—C13B—C26B78.3 (3)
C16A—C12A—C13A—C14A−41.5 (2)C24B—C12B—C13B—C26B−49.5 (3)
C26A—C13A—C14A—C15A151.6 (2)C16B—C12B—C13B—C26B−167.3 (2)
C12A—C13A—C14A—C15A21.8 (3)C11B—C12B—C13B—C14B−155.0 (2)
C13A—C14A—C15A—C16A7.0 (3)C24B—C12B—C13B—C14B77.3 (2)
C14A—C15A—C16A—C17A−162.9 (2)C16B—C12B—C13B—C14B−40.6 (2)
C14A—C15A—C16A—C12A−34.0 (3)C26B—C13B—C14B—C15B152.4 (2)
C11A—C12A—C16A—C17A−58.9 (3)C12B—C13B—C14B—C15B20.9 (3)
C24A—C12A—C16A—C17A62.4 (3)C13B—C14B—C15B—C16B8.1 (3)
C13A—C12A—C16A—C17A178.5 (2)C14B—C15B—C16B—C17B−163.6 (2)
C11A—C12A—C16A—C15A169.9 (2)C14B—C15B—C16B—C12B−34.4 (3)
C24A—C12A—C16A—C15A−68.8 (3)C11B—C12B—C16B—C15B168.6 (2)
C13A—C12A—C16A—C15A47.3 (2)C24B—C12B—C16B—C15B−69.6 (3)
C15A—C16A—C17A—C1A−55.1 (3)C13B—C12B—C16B—C15B47.1 (2)
C12A—C16A—C17A—C1A−179.1 (2)C11B—C12B—C16B—C17B−58.9 (3)
C15A—C16A—C17A—C9A−178.2 (2)C24B—C12B—C16B—C17B62.9 (3)
C12A—C16A—C17A—C9A57.7 (3)C13B—C12B—C16B—C17B179.58 (19)
C2A—C1A—C17A—C16A−163.5 (2)C15B—C16B—C17B—C1B−48.9 (3)
C2A—C1A—C17A—C9A−41.8 (3)C12B—C16B—C17B—C1B−173.71 (19)
C10A—C9A—C17A—C16A−52.2 (3)C15B—C16B—C17B—C9B−173.0 (2)
C8A—C9A—C17A—C16A177.8 (2)C12B—C16B—C17B—C9B62.2 (3)
C10A—C9A—C17A—C1A−174.7 (2)C2B—C1B—C17B—C16B−166.9 (2)
C8A—C9A—C17A—C1A55.3 (3)C2B—C1B—C17B—C9B−45.7 (3)
N1A—N2A—C18A—O3A174.5 (2)C10B—C9B—C17B—C16B−57.9 (3)
N1A—N2A—C18A—C19A−4.8 (4)C8B—C9B—C17B—C16B173.0 (2)
O3A—C18A—C19A—C20A36.2 (4)C10B—C9B—C17B—C1B178.3 (2)
N2A—C18A—C19A—C20A−144.5 (3)C8B—C9B—C17B—C1B49.2 (3)
C5A—O1A—C21A—O2A3.5 (4)N1B—N2B—C18B—O3B−173.1 (2)
C5A—O1A—C21A—C22A−179.1 (2)N1B—N2B—C18B—C19B8.4 (3)
C14A—C13A—C26A—C27X46.7 (12)O3B—C18B—C19B—C20B113.1 (3)
C12A—C13A—C26A—C27X167.2 (12)N2B—C18B—C19B—C20B−68.3 (3)
C14A—C13A—C26A—C25A−172.7 (2)C5B—O1B—C21B—O2B7.5 (4)
C12A—C13A—C26A—C25A−52.2 (3)C5B—O1B—C21B—C22B−171.9 (2)
C14A—C13A—C26A—C27A65.9 (3)C12B—C13B—C26B—C25B−48.8 (3)
C12A—C13A—C26A—C27A−173.6 (2)C14B—C13B—C26B—C25B−171.4 (2)
C27X—C26A—C27A—C28A−35 (3)C12B—C13B—C26B—C27B−171.7 (2)
C25A—C26A—C27A—C28A69.0 (4)C14B—C13B—C26B—C27B65.7 (3)
C13A—C26A—C27A—C28A−167.2 (3)C25B—C26B—C27B—C28B58.5 (3)
C26A—C27A—C28A—C29A−179.5 (3)C13B—C26B—C27B—C28B−177.2 (2)
C27A—C28A—C29A—C30A60.4 (5)C26B—C27B—C28B—C29B179.8 (3)
C28A—C29A—C30A—C32A173.3 (3)C27B—C28B—C29B—C30B167.3 (3)
C28A—C29A—C30A—C31A51.3 (4)C28B—C29B—C30B—C31Y75.6 (10)
C25A—C26A—C27X—C28X−74.9 (16)C28B—C29B—C30B—C31B51.0 (5)
C13A—C26A—C27X—C28X65.8 (17)C28B—C29B—C30B—C32Y−158.5 (8)
C27A—C26A—C27X—C28X9.2 (16)C28B—C29B—C30B—C32B170.0 (6)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O3B0.85 (3)2.09 (3)2.932 (3)170 (3)
N2B—H1NB···O3A0.88 (3)2.11 (3)2.963 (3)163 (3)
C1A—H1AB···O3B0.972.393.201 (3)140
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5021).
References
  • Ahmed, S. & Boruah, R. C. (1996). Tetrahedron Lett. 37, 8231–8232.
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Banday, A. H., Mir, B. P., Lone, I. H., Suri, K. A. & Sampath Kumar, H. M. (2010). Steroids, 75, 805–809. [PubMed]
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  • Bruker (2009). SADABS, APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  • Doorenbos, N. J. & Wu, M. T. (1968). J. Med. Chem. 11, 158–159. [PubMed]
  • Drach, S. V., Litvinovskaya, R. P. & Kripach, V. A. (2000). Chem. Hetrocyclic Compd, 36, 233–255.
  • Gupta, A. K., Jadav, K. M., Patro, B., Ila, H. & Junjappa, H. (1995). Synthesis, pp. 841–844.
  • Ketuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o773–o774. [PMC free article] [PubMed]
  • Khan, S. A., Saleem, K. & Khan, Z. (2007). Eur. J. Med. Chem. 42, 103–108. [PubMed]
  • Khan, M. S., Sulaiman, O., Hashim, R., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o1368. [PMC free article] [PubMed]
  • Khan, S. A. & Yusuf, M. (2009). Eur. J. Med. Chem. 44, 2597–2600. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Short, F. W. & Long, L. U. (1969). J. Heterocycl. Chem. 5, 707–710.
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
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