PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2011 July 1; 67(Pt 7): o1772.
Published online 2011 June 22. doi:  10.1107/S1600536811023294
PMCID: PMC3152030

Ethyl 1-[2-(morpholin-4-yl)eth­yl]-2-[4-(morpholin-4-yl)phen­yl]-1H-1,3-benzimidazole-5-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C26H32N4O4, consists of two independent mol­ecules. In both mol­ecules, the eth­oxy groups are each disordered over two sets of sites with occupancies of 0.695 (4):0.305 (4) and 0.877 (2):0.123 (2). The dihedral angles between the benzimidazole ring system and the adjacent benzene ring in the two mol­ecules are 41.41 (5) and 31.46 (5)°. In the crystal, mol­ecules are linked by C—H(...)O and C—H(...)N inter­actions.

Related literature

For biological activity of benzimidazole derivatives, see: Vijaya et al. (2009 [triangle]); Haugwitz (1982 [triangle]); Hisano (1982 [triangle]). For the 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-67-o1772-scheme1.jpg

Experimental

Crystal data

  • C26H32N4O4
  • M r = 464.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-67-o1772-efi1.jpg
  • a = 10.3595 (3) Å
  • b = 20.6870 (6) Å
  • c = 23.7904 (7) Å
  • β = 112.839 (2)°
  • V = 4698.7 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.50 × 0.27 × 0.14 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.957, T max = 0.987
  • 100050 measured reflections
  • 20532 independent reflections
  • 13488 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.154
  • S = 1.02
  • 20532 reflections
  • 667 parameters
  • 78 restraints
  • H-atom parameters constrained
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.34 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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023294/is2728sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023294/is2728Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023294/is2728Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors wish to express their thanks to Universiti Sains Malaysia (USM), Penang, Malaysia, for providing research facilities. HKF also thanks USM for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

The benzimidazole nucleus is an important heterocyclic ring because of its synthetic utility and broad range of pharmacological activities. Benzimidazole derivatives exhibit different pharmacological effects, including antifungal. In recent years, attention has increasingly been given to the synthesis of benzimidazole derivatives as a source of new antimicrobial agents (Vijaya et al., 2009). Recent observations suggest that substituted benzimidazoles and heterocyclic, which are the structural isosters of nucleotides owing to the fused heterocyclic nuclei in their structures that allow them to interact easily with the biopolymers, possess potential activity with lower toxicities in the chemotherapeutic approach in man (Haugwitz, 1982; Hisano, 1982).

In the asymmetric unit (Fig. 1) of the title compound there are two molecules. In both molecules, the ethoxy group were disordered over two position with the refined occupancies of 0.695:0.305 and 0.877:0.123, respectively, for the molecules A and B. The benzimidazole (N1/N2/C1–C7) ring in both molecules is planar with the maximum deviation of 0.0129 (12) from atom C5A and -0.0246 (12) from atom C2B. It makes dihedral angles of 41.41 (5)° and 31.46 (5)° with the adjacent benzene ring, respectively, for molecule A and B. All the four morpholine rings, O2A/N3A/C23A–C26A, O3A/N4A/C14A–C17A, O2B/N3B/C23B–C26B and O3B/N4B/C14B–C17B, adopt chair conformations with [Q = 0.5722 (13)Å, θ = 1.51 (13)° & [var phi] = 127 (5)°], [Q = 0.5411 (12)Å, θ = 8.99 (12)° & [var phi] = 354.4 (9)], [Q = 0.5787 (12)Å, θ = 177.48 (12)° & [var phi] = 58 (3)] and [Q = 0.5389 (14)Å, θ = 170.19 (14)° & [var phi] = 182.8 (10)°], respectively.

In the crystal structure, molecules A and B are linked by C25B—H25C···N3A hydrogen bond. The molecules are further linked by C14B—H14D···O4Ai, C17B—H17C···O3Aiii, C23B—H23D···O2Aiv and C24B—H24D···N1Bv hydrogen bonds (Table 1) to form layers that are connected by a C16B—H16C···O1Bii interaction (Fig. 2).

Experimental

Ethlyl-3-amino-4-(morpholinoethylamino) benzoate (0.01 mol) and sodium metabisulfite adduct of 4-morpholino benzaldehyde (0.01 mol) were dissolved in DMF. The reaction mixture was refluxed at 130 °C for 4 hrs. After completion, the reaction mixture was diluted in ethyl acetate (20 mL) and washed with water (20 mL). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate.

Refinement

The ethoxy group was disordered over two position with the refined occupancies of 0.695 (4):0.305 (4) and 0.877 (2):0.123 (2). The same Uij parameters were applied to the C19Y/C19B pair. Similarity restraints were used on the disordered part of the molecular structure. All H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

Crystal data

C26H32N4O4F(000) = 1984
Mr = 464.56Dx = 1.313 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9803 reflections
a = 10.3595 (3) Åθ = 3.0–34.4°
b = 20.6870 (6) ŵ = 0.09 mm1
c = 23.7904 (7) ÅT = 100 K
β = 112.839 (2)°Block, colourless
V = 4698.7 (2) Å30.50 × 0.27 × 0.14 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer20532 independent reflections
Radiation source: fine-focus sealed tube13488 reflections with I > 2σ(I)
graphiteRint = 0.042
[var phi] and ω scansθmax = 34.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −16→16
Tmin = 0.957, Tmax = 0.987k = −33→33
100050 measured reflectionsl = −38→38

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) = 0.154H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.072P)2 + 0.8073P] where P = (Fo2 + 2Fc2)/3
20532 reflections(Δ/σ)max = 0.001
667 parametersΔρmax = 0.45 e Å3
78 restraintsΔρmin = −0.34 e Å3

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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
O1A0.2415 (2)0.93334 (9)0.95927 (9)0.0270 (4)0.695 (4)
C19A0.2018 (2)0.94515 (10)1.01053 (9)0.0299 (5)0.695 (4)
H19A0.13070.97991.00020.036*0.695 (4)
H19B0.28470.95921.04640.036*0.695 (4)
C20A0.1435 (3)0.88436 (12)1.02530 (10)0.0355 (5)0.695 (4)
H20A0.11150.89271.05830.053*0.695 (4)
H20B0.21640.85101.03820.053*0.695 (4)
H20C0.06440.86950.98910.053*0.695 (4)
O1X0.2849 (6)0.9144 (2)0.9683 (2)0.0293 (9)0.305 (4)
C19X0.2621 (6)0.9137 (3)1.0258 (2)0.0365 (13)0.305 (4)
H19C0.29340.87201.04700.044*0.305 (4)
H19D0.31650.94881.05300.044*0.305 (4)
C20X0.1115 (6)0.9230 (4)1.0108 (3)0.0565 (19)0.305 (4)
H20D0.09320.92051.04820.085*0.305 (4)
H20E0.05830.88910.98240.085*0.305 (4)
H20F0.08260.96540.99180.085*0.305 (4)
O4A0.32655 (15)1.03045 (5)0.97339 (5)0.0584 (4)
C18A0.30702 (15)0.98036 (6)0.94559 (6)0.0340 (3)
O2A0.65322 (9)0.72303 (4)0.62040 (4)0.03086 (19)
O3A0.88432 (10)1.22442 (4)0.54127 (4)0.02935 (19)
N1A0.50149 (10)1.05538 (4)0.79633 (4)0.02112 (18)
N2A0.44017 (10)0.96405 (4)0.74025 (4)0.01775 (16)
N3A0.53247 (10)0.81363 (4)0.67653 (4)0.01855 (17)
N4A0.70676 (10)1.15637 (4)0.58792 (4)0.01836 (16)
C1A0.43668 (12)1.01324 (5)0.82253 (5)0.01989 (19)
C2A0.40671 (13)1.02074 (5)0.87442 (5)0.0235 (2)
H2AA0.43181.05910.89810.028*
C3A0.33901 (13)0.97032 (5)0.89054 (5)0.0240 (2)
C4A0.29955 (12)0.91355 (5)0.85502 (5)0.0234 (2)
H4AA0.25340.88000.86720.028*
C5A0.32675 (12)0.90580 (5)0.80282 (5)0.0218 (2)
H5AA0.29850.86810.77830.026*
C6A0.39752 (11)0.95603 (5)0.78793 (5)0.01851 (19)
C7A0.50214 (11)1.02455 (5)0.74764 (5)0.01805 (18)
C8A0.55510 (11)1.05466 (5)0.70493 (5)0.01805 (18)
C9A0.63634 (11)1.02339 (5)0.67810 (5)0.01807 (18)
H9AA0.65620.97860.68560.022*
C10A0.68876 (11)1.05649 (5)0.64056 (5)0.01800 (18)
H10A0.74511.03410.62360.022*
C11A0.65970 (11)1.12262 (4)0.62729 (5)0.01684 (18)
C12A0.57768 (11)1.15376 (5)0.65446 (5)0.01919 (19)
H12A0.55631.19840.64660.023*
C13A0.52778 (11)1.12075 (5)0.69227 (5)0.01935 (19)
H13A0.47351.14330.71020.023*
C14A0.80102 (12)1.12200 (5)0.56573 (5)0.0222 (2)
H14A0.75761.08050.54720.027*
H14B0.88971.11220.60050.027*
C15A0.83236 (15)1.16150 (5)0.51881 (6)0.0281 (2)
H15A0.90261.13850.50760.034*
H15B0.74581.16590.48160.034*
C16A0.78096 (13)1.25783 (5)0.55526 (5)0.0243 (2)
H16A0.69411.26110.51800.029*
H16B0.81421.30220.56890.029*
C17A0.74900 (13)1.22394 (5)0.60451 (5)0.0247 (2)
H17A0.83301.22490.64310.030*
H17B0.67271.24710.61130.030*
C21A0.42635 (11)0.91451 (5)0.69454 (5)0.01818 (19)
H21A0.43710.93440.65880.022*
H21B0.33210.89470.68070.022*
C22A0.53814 (12)0.86238 (5)0.72165 (5)0.01854 (19)
H22A0.63190.88280.73760.022*
H22B0.52420.84130.75620.022*
C23A0.59041 (14)0.75174 (5)0.70504 (5)0.0257 (2)
H23A0.53840.73630.72970.031*
H23B0.68980.75750.73260.031*
C24A0.57951 (14)0.70230 (5)0.65659 (6)0.0309 (3)
H24A0.61860.66060.67630.037*
H24B0.47970.69540.63010.037*
C25A0.59904 (16)0.78334 (6)0.59223 (6)0.0337 (3)
H25A0.50010.77770.56410.040*
H25B0.65260.79770.56790.040*
C26A0.60758 (14)0.83473 (5)0.63877 (5)0.0261 (2)
H26A0.70690.84310.66500.031*
H26B0.56600.87550.61760.031*
O1B−0.19358 (12)0.57969 (4)0.96297 (5)0.0219 (2)0.877 (2)
C19B−0.22170 (16)0.57394 (7)1.01799 (6)0.0227 (3)0.877 (2)
H19E−0.18610.61281.04360.027*0.877 (2)
H19F−0.17150.53581.04160.027*0.877 (2)
C20B−0.37591 (16)0.56685 (7)1.00312 (7)0.0288 (3)0.877 (2)
H20G−0.39150.56141.04090.043*0.877 (2)
H20H−0.41170.52890.97700.043*0.877 (2)
H20I−0.42510.60560.98170.043*0.877 (2)
O1Y−0.2819 (8)0.5744 (3)0.9371 (3)0.0205 (16)0.123 (2)
C19Y−0.3365 (11)0.5667 (4)0.9848 (4)0.0227 (3)0.123 (2)
H19G−0.38430.52430.97990.027*0.123 (2)
H19H−0.40640.60090.98060.027*0.123 (2)
C20Y−0.2242 (17)0.5704 (6)1.0454 (6)0.055 (4)0.123 (2)
H20J−0.26420.56721.07650.082*0.123 (2)
H20K−0.17490.61161.04980.082*0.123 (2)
H20L−0.15840.53471.05060.082*0.123 (2)
O2B0.11661 (9)0.81572 (4)0.64074 (4)0.02732 (18)
O3B0.39165 (11)0.26192 (4)0.53919 (4)0.0364 (2)
O4B−0.19219 (12)0.47120 (4)0.95706 (4)0.0388 (2)
N1B0.00759 (10)0.44467 (4)0.78758 (4)0.01896 (17)
N2B−0.03377 (9)0.53852 (4)0.73501 (4)0.01702 (16)
N3B0.07264 (9)0.68721 (4)0.67357 (4)0.01652 (16)
N4B0.22233 (10)0.33681 (4)0.58525 (4)0.02010 (17)
C1B−0.05338 (11)0.48833 (5)0.81388 (5)0.01751 (18)
C2B−0.09119 (11)0.48028 (5)0.86352 (5)0.01917 (19)
H2BA−0.07850.44000.88420.023*
C3B−0.14824 (12)0.53308 (5)0.88195 (5)0.01954 (19)
C4B−0.17133 (12)0.59237 (5)0.85032 (5)0.0200 (2)
H4BA−0.21000.62760.86410.024*
C5B−0.13871 (11)0.60035 (5)0.79940 (5)0.01915 (19)
H5BA−0.15630.63990.77740.023*
C6B−0.07888 (11)0.54750 (5)0.78206 (5)0.01699 (18)
C7B0.01755 (11)0.47587 (4)0.74094 (5)0.01714 (18)
C8B0.07101 (11)0.44370 (4)0.69932 (5)0.01733 (18)
C9B0.14730 (12)0.47348 (5)0.66935 (5)0.01917 (19)
H9BA0.16390.51870.67400.023*
C10B0.19928 (12)0.43860 (5)0.63303 (5)0.0198 (2)
H10B0.25230.46030.61390.024*
C11B0.17522 (11)0.37157 (4)0.62379 (5)0.01771 (18)
C12B0.10018 (11)0.34142 (5)0.65489 (5)0.0200 (2)
H12B0.08350.29620.65050.024*
C13B0.05040 (11)0.37662 (5)0.69163 (5)0.01927 (19)
H13B0.00090.35490.71230.023*
C14B0.33434 (16)0.36593 (5)0.57065 (6)0.0337 (3)
H14C0.42110.36780.60810.040*
H14D0.30790.41080.55620.040*
C15B0.3625 (2)0.32821 (6)0.52222 (7)0.0430 (4)
H15C0.27980.33100.48320.052*
H15D0.44330.34750.51590.052*
C16B0.27266 (15)0.23460 (6)0.54554 (6)0.0325 (3)
H16C0.28980.18800.55510.039*
H16D0.19110.23840.50630.039*
C17B0.23841 (14)0.26695 (5)0.59500 (5)0.0253 (2)
H17C0.15050.24860.59540.030*
H17D0.31430.25820.63520.030*
C18B−0.18227 (14)0.52350 (5)0.93653 (5)0.0261 (2)
C21B−0.04038 (11)0.58836 (4)0.69036 (5)0.01778 (18)
H21C−0.12750.61380.68020.021*
H21D−0.04280.56760.65250.021*
C22B0.08605 (11)0.63358 (4)0.71524 (5)0.01756 (18)
H22C0.09420.65070.75530.021*
H22D0.17240.60900.72130.021*
C23B0.00437 (12)0.74301 (5)0.68820 (5)0.01995 (19)
H23C0.06180.75850.72980.024*
H23D−0.08840.73000.68730.024*
C24B−0.01374 (12)0.79682 (5)0.64282 (5)0.0234 (2)
H24C−0.07770.78230.60180.028*
H24D−0.05720.83460.65420.028*
C25B0.18245 (13)0.76127 (5)0.62602 (6)0.0254 (2)
H25C0.27310.77470.62490.030*
H25D0.12240.74490.58510.030*
C26B0.20698 (11)0.70785 (5)0.67282 (5)0.0210 (2)
H26C0.25380.67080.66240.025*
H26D0.26860.72380.71370.025*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0384 (11)0.0220 (8)0.0295 (8)0.0021 (6)0.0229 (8)0.0008 (6)
C19A0.0407 (12)0.0294 (9)0.0318 (9)0.0027 (8)0.0273 (9)0.0008 (7)
C20A0.0469 (13)0.0392 (11)0.0286 (10)−0.0097 (10)0.0236 (9)−0.0034 (8)
O1X0.043 (3)0.026 (2)0.0276 (18)−0.0087 (16)0.0228 (19)−0.0077 (15)
C19X0.045 (3)0.033 (2)0.036 (2)−0.001 (2)0.021 (2)−0.0047 (18)
C20X0.045 (3)0.078 (5)0.044 (3)−0.007 (3)0.014 (3)−0.022 (3)
O4A0.1043 (11)0.0402 (6)0.0580 (7)−0.0108 (6)0.0614 (8)−0.0178 (5)
C18A0.0456 (8)0.0327 (6)0.0333 (7)−0.0052 (6)0.0258 (6)−0.0059 (5)
O2A0.0288 (5)0.0295 (4)0.0368 (5)0.0026 (4)0.0156 (4)−0.0117 (4)
O3A0.0365 (5)0.0203 (4)0.0390 (5)−0.0063 (3)0.0232 (4)−0.0033 (3)
N1A0.0272 (5)0.0151 (4)0.0225 (4)−0.0002 (3)0.0111 (4)−0.0016 (3)
N2A0.0210 (4)0.0145 (3)0.0193 (4)−0.0011 (3)0.0097 (3)−0.0026 (3)
N3A0.0215 (4)0.0151 (3)0.0216 (4)−0.0006 (3)0.0111 (4)−0.0024 (3)
N4A0.0221 (4)0.0127 (3)0.0217 (4)−0.0011 (3)0.0101 (4)−0.0010 (3)
C1A0.0247 (5)0.0151 (4)0.0210 (5)0.0009 (4)0.0102 (4)−0.0014 (3)
C2A0.0316 (6)0.0183 (4)0.0230 (5)0.0003 (4)0.0135 (5)−0.0040 (4)
C3A0.0288 (6)0.0235 (5)0.0238 (5)0.0018 (4)0.0146 (5)−0.0015 (4)
C4A0.0256 (6)0.0222 (5)0.0261 (5)−0.0028 (4)0.0140 (5)−0.0013 (4)
C5A0.0241 (5)0.0195 (4)0.0244 (5)−0.0030 (4)0.0121 (4)−0.0035 (4)
C6A0.0206 (5)0.0161 (4)0.0198 (5)0.0009 (4)0.0089 (4)−0.0017 (3)
C7A0.0206 (5)0.0140 (4)0.0203 (5)0.0005 (3)0.0086 (4)−0.0007 (3)
C8A0.0196 (5)0.0143 (4)0.0197 (5)−0.0005 (3)0.0071 (4)−0.0011 (3)
C9A0.0207 (5)0.0126 (4)0.0205 (5)0.0004 (3)0.0075 (4)−0.0006 (3)
C10A0.0198 (5)0.0143 (4)0.0205 (5)0.0006 (3)0.0085 (4)−0.0017 (3)
C11A0.0177 (5)0.0135 (4)0.0183 (4)−0.0007 (3)0.0059 (4)−0.0008 (3)
C12A0.0205 (5)0.0128 (4)0.0246 (5)0.0019 (3)0.0092 (4)0.0006 (3)
C13A0.0200 (5)0.0145 (4)0.0241 (5)0.0009 (4)0.0092 (4)−0.0018 (3)
C14A0.0275 (6)0.0173 (4)0.0258 (5)0.0011 (4)0.0145 (5)−0.0007 (4)
C15A0.0422 (7)0.0185 (4)0.0314 (6)−0.0037 (5)0.0229 (6)−0.0010 (4)
C16A0.0300 (6)0.0167 (4)0.0274 (5)−0.0036 (4)0.0124 (5)−0.0013 (4)
C17A0.0342 (6)0.0143 (4)0.0297 (6)−0.0053 (4)0.0167 (5)−0.0038 (4)
C21A0.0208 (5)0.0156 (4)0.0188 (5)−0.0014 (4)0.0083 (4)−0.0040 (3)
C22A0.0232 (5)0.0155 (4)0.0179 (4)0.0012 (4)0.0090 (4)−0.0015 (3)
C23A0.0340 (6)0.0153 (4)0.0316 (6)0.0028 (4)0.0166 (5)0.0009 (4)
C24A0.0316 (7)0.0191 (5)0.0438 (7)−0.0012 (4)0.0168 (6)−0.0087 (5)
C25A0.0414 (8)0.0364 (6)0.0279 (6)0.0055 (6)0.0186 (6)−0.0062 (5)
C26A0.0347 (7)0.0237 (5)0.0270 (6)−0.0007 (5)0.0197 (5)−0.0013 (4)
O1B0.0306 (6)0.0160 (4)0.0227 (5)0.0003 (4)0.0144 (5)−0.0005 (3)
C19B0.0305 (7)0.0211 (5)0.0170 (6)0.0020 (5)0.0097 (5)−0.0001 (5)
C20B0.0313 (8)0.0348 (7)0.0234 (7)0.0024 (6)0.0139 (6)0.0008 (5)
O1Y0.022 (4)0.021 (3)0.023 (3)0.004 (3)0.015 (3)0.002 (2)
C19Y0.0305 (7)0.0211 (5)0.0170 (6)0.0020 (5)0.0097 (5)−0.0001 (5)
C20Y0.087 (12)0.027 (6)0.061 (10)−0.015 (6)0.041 (10)−0.009 (7)
O2B0.0342 (5)0.0143 (3)0.0374 (5)−0.0017 (3)0.0182 (4)0.0026 (3)
O3B0.0621 (7)0.0212 (4)0.0414 (5)0.0092 (4)0.0370 (5)0.0028 (4)
O4B0.0762 (8)0.0163 (4)0.0424 (5)0.0007 (4)0.0433 (6)0.0019 (3)
N1B0.0234 (5)0.0133 (3)0.0228 (4)−0.0002 (3)0.0119 (4)0.0011 (3)
N2B0.0207 (4)0.0127 (3)0.0193 (4)−0.0002 (3)0.0095 (3)0.0011 (3)
N3B0.0187 (4)0.0117 (3)0.0209 (4)0.0008 (3)0.0096 (3)0.0019 (3)
N4B0.0262 (5)0.0143 (3)0.0201 (4)0.0020 (3)0.0093 (4)−0.0020 (3)
C1B0.0196 (5)0.0128 (4)0.0212 (5)−0.0010 (3)0.0091 (4)0.0007 (3)
C2B0.0234 (5)0.0131 (4)0.0232 (5)−0.0014 (4)0.0114 (4)0.0010 (3)
C3B0.0247 (5)0.0143 (4)0.0224 (5)−0.0013 (4)0.0123 (4)0.0001 (3)
C4B0.0230 (5)0.0153 (4)0.0241 (5)0.0015 (4)0.0119 (4)0.0010 (3)
C5B0.0223 (5)0.0139 (4)0.0227 (5)0.0016 (4)0.0103 (4)0.0024 (3)
C6B0.0184 (5)0.0149 (4)0.0185 (4)−0.0013 (3)0.0080 (4)0.0002 (3)
C7B0.0193 (5)0.0126 (4)0.0206 (5)−0.0014 (3)0.0089 (4)−0.0003 (3)
C8B0.0196 (5)0.0129 (4)0.0206 (5)−0.0009 (3)0.0089 (4)−0.0010 (3)
C9B0.0252 (5)0.0124 (4)0.0227 (5)−0.0020 (4)0.0124 (4)−0.0017 (3)
C10B0.0273 (6)0.0135 (4)0.0219 (5)−0.0011 (4)0.0132 (4)−0.0006 (3)
C11B0.0206 (5)0.0137 (4)0.0177 (4)0.0014 (3)0.0062 (4)−0.0012 (3)
C12B0.0226 (5)0.0120 (4)0.0253 (5)−0.0013 (4)0.0093 (4)−0.0014 (3)
C13B0.0217 (5)0.0126 (4)0.0252 (5)−0.0011 (3)0.0110 (4)0.0002 (3)
C14B0.0572 (9)0.0205 (5)0.0409 (7)−0.0025 (5)0.0381 (7)−0.0042 (5)
C15B0.0853 (12)0.0207 (5)0.0445 (8)0.0091 (6)0.0486 (9)0.0035 (5)
C16B0.0480 (8)0.0197 (5)0.0316 (6)0.0025 (5)0.0174 (6)−0.0071 (4)
C17B0.0346 (6)0.0143 (4)0.0314 (6)0.0005 (4)0.0177 (5)−0.0035 (4)
C18B0.0393 (7)0.0170 (4)0.0294 (6)0.0015 (4)0.0213 (5)0.0005 (4)
C21B0.0208 (5)0.0135 (4)0.0190 (5)−0.0005 (3)0.0078 (4)0.0027 (3)
C22B0.0193 (5)0.0135 (4)0.0192 (5)0.0001 (3)0.0067 (4)0.0021 (3)
C23B0.0230 (5)0.0148 (4)0.0241 (5)0.0029 (4)0.0114 (4)0.0013 (3)
C24B0.0264 (6)0.0152 (4)0.0284 (5)0.0031 (4)0.0105 (5)0.0028 (4)
C25B0.0307 (6)0.0194 (4)0.0318 (6)−0.0014 (4)0.0185 (5)0.0031 (4)
C26B0.0203 (5)0.0178 (4)0.0263 (5)−0.0007 (4)0.0108 (4)0.0008 (4)

Geometric parameters (Å, °)

O1A—C18A1.298 (2)O1B—C18B1.3484 (13)
O1A—C19A1.451 (2)O1B—C19B1.4520 (16)
C19A—C20A1.495 (3)C19B—C20B1.503 (2)
C19A—H19A0.9900C19B—H19E0.9900
C19A—H19B0.9900C19B—H19F0.9900
C20A—H20A0.9800C20B—H20G0.9800
C20A—H20B0.9800C20B—H20H0.9800
C20A—H20C0.9800C20B—H20I0.9800
O1X—C19X1.475 (6)O1Y—C19Y1.459 (10)
O1X—C18A1.517 (5)O1Y—C18B1.478 (6)
C19X—C20X1.473 (8)C19Y—C20Y1.461 (14)
C19X—H19C0.9900C19Y—H19G0.9900
C19X—H19D0.9900C19Y—H19H0.9900
C20X—H20D0.9800C20Y—H20J0.9800
C20X—H20E0.9800C20Y—H20K0.9800
C20X—H20F0.9800C20Y—H20L0.9800
O4A—C18A1.2033 (15)O2B—C24B1.4251 (14)
C18A—C3A1.4852 (16)O2B—C25B1.4290 (14)
O2A—C24A1.4208 (16)O3B—C16B1.4164 (17)
O2A—C25A1.4243 (16)O3B—C15B1.4283 (14)
O3A—C16A1.4181 (14)O4B—C18B1.2077 (13)
O3A—C15A1.4305 (14)N1B—C7B1.3220 (13)
N1A—C7A1.3247 (13)N1B—C1B1.3830 (13)
N1A—C1A1.3872 (14)N2B—C6B1.3827 (13)
N2A—C6A1.3780 (13)N2B—C7B1.3871 (12)
N2A—C7A1.3862 (13)N2B—C21B1.4627 (12)
N2A—C21A1.4602 (12)N3B—C22B1.4583 (12)
N3A—C22A1.4575 (12)N3B—C26B1.4624 (13)
N3A—C23A1.4641 (14)N3B—C23B1.4645 (13)
N3A—C26A1.4648 (14)N4B—C11B1.3942 (13)
N4A—C11A1.3988 (13)N4B—C17B1.4629 (13)
N4A—C14A1.4622 (13)N4B—C14B1.4637 (15)
N4A—C17A1.4721 (13)C1B—C2B1.3910 (14)
C1A—C2A1.3936 (14)C1B—C6B1.4093 (13)
C1A—C6A1.4083 (14)C2B—C3B1.3912 (14)
C2A—C3A1.3911 (16)C2B—H2BA0.9500
C2A—H2AA0.9500C3B—C4B1.4101 (14)
C3A—C4A1.4113 (15)C3B—C18B1.4849 (15)
C4A—C5A1.3854 (15)C4B—C5B1.3880 (14)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.3943 (14)C5B—C6B1.3959 (14)
C5A—H5AA0.9500C5B—H5BA0.9500
C7A—C8A1.4676 (14)C7B—C8B1.4682 (14)
C8A—C9A1.3969 (14)C8B—C9B1.3965 (14)
C8A—C13A1.4051 (14)C8B—C13B1.4050 (13)
C9A—C10A1.3922 (14)C9B—C10B1.3852 (14)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.4099 (13)C10B—C11B1.4108 (13)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.4077 (14)C11B—C12B1.4096 (14)
C12A—C13A1.3796 (14)C12B—C13B1.3822 (14)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.5167 (15)C14B—C15B1.5106 (16)
C14A—H14A0.9900C14B—H14C0.9900
C14A—H14B0.9900C14B—H14D0.9900
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
C16A—C17A1.5084 (15)C16B—C17B1.5108 (16)
C16A—H16A0.9900C16B—H16C0.9900
C16A—H16B0.9900C16B—H16D0.9900
C17A—H17A0.9900C17B—H17C0.9900
C17A—H17B0.9900C17B—H17D0.9900
C21A—C22A1.5298 (14)C21B—C22B1.5294 (14)
C21A—H21A0.9900C21B—H21C0.9900
C21A—H21B0.9900C21B—H21D0.9900
C22A—H22A0.9900C22B—H22C0.9900
C22A—H22B0.9900C22B—H22D0.9900
C23A—C24A1.5120 (16)C23B—C24B1.5108 (14)
C23A—H23A0.9900C23B—H23C0.9900
C23A—H23B0.9900C23B—H23D0.9900
C24A—H24A0.9900C24B—H24C0.9900
C24A—H24B0.9900C24B—H24D0.9900
C25A—C26A1.5125 (16)C25B—C26B1.5185 (15)
C25A—H25A0.9900C25B—H25C0.9900
C25A—H25B0.9900C25B—H25D0.9900
C26A—H26A0.9900C26B—H26C0.9900
C26A—H26B0.9900C26B—H26D0.9900
C18A—O1A—C19A115.53 (16)C18B—O1B—C19B115.73 (9)
O1A—C19A—C20A109.17 (16)O1B—C19B—C20B111.26 (13)
O1A—C19A—H19A109.8O1B—C19B—H19E109.4
C20A—C19A—H19A109.8C20B—C19B—H19E109.4
O1A—C19A—H19B109.8O1B—C19B—H19F109.4
C20A—C19A—H19B109.8C20B—C19B—H19F109.4
H19A—C19A—H19B108.3H19E—C19B—H19F108.0
C19X—O1X—C18A116.1 (3)C19Y—O1Y—C18B114.4 (6)
C20X—C19X—O1X108.0 (4)O1Y—C19Y—C20Y111.1 (11)
C20X—C19X—H19C110.1O1Y—C19Y—H19G109.4
O1X—C19X—H19C110.1C20Y—C19Y—H19G109.4
C20X—C19X—H19D110.1O1Y—C19Y—H19H109.4
O1X—C19X—H19D110.1C20Y—C19Y—H19H109.4
H19C—C19X—H19D108.4H19G—C19Y—H19H108.0
C19X—C20X—H20D109.5C19Y—C20Y—H20J109.5
C19X—C20X—H20E109.5C19Y—C20Y—H20K109.5
H20D—C20X—H20E109.5H20J—C20Y—H20K109.5
C19X—C20X—H20F109.5C19Y—C20Y—H20L109.5
H20D—C20X—H20F109.5H20J—C20Y—H20L109.5
H20E—C20X—H20F109.5H20K—C20Y—H20L109.5
O4A—C18A—O1A120.02 (14)C24B—O2B—C25B109.94 (8)
O4A—C18A—C3A123.89 (12)C16B—O3B—C15B108.41 (11)
O1A—C18A—C3A115.71 (13)C7B—N1B—C1B105.01 (8)
O4A—C18A—O1X126.49 (19)C6B—N2B—C7B106.24 (8)
C3A—C18A—O1X107.76 (18)C6B—N2B—C21B123.92 (8)
C24A—O2A—C25A110.06 (9)C7B—N2B—C21B129.83 (8)
C16A—O3A—C15A108.79 (9)C22B—N3B—C26B112.98 (8)
C7A—N1A—C1A104.94 (8)C22B—N3B—C23B111.44 (8)
C6A—N2A—C7A106.55 (8)C26B—N3B—C23B108.81 (8)
C6A—N2A—C21A123.95 (8)C11B—N4B—C17B116.91 (9)
C7A—N2A—C21A129.41 (8)C11B—N4B—C14B117.12 (8)
C22A—N3A—C23A111.83 (8)C17B—N4B—C14B113.09 (9)
C22A—N3A—C26A111.49 (8)N1B—C1B—C2B129.38 (9)
C23A—N3A—C26A108.96 (9)N1B—C1B—C6B110.34 (9)
C11A—N4A—C14A117.01 (8)C2B—C1B—C6B120.27 (9)
C11A—N4A—C17A116.04 (8)C1B—C2B—C3B117.89 (9)
C14A—N4A—C17A112.82 (9)C1B—C2B—H2BA121.1
N1A—C1A—C2A129.88 (9)C3B—C2B—H2BA121.1
N1A—C1A—C6A110.21 (9)C2B—C3B—C4B121.30 (9)
C2A—C1A—C6A119.91 (10)C2B—C3B—C18B116.41 (9)
C3A—C2A—C1A118.05 (10)C4B—C3B—C18B122.28 (9)
C3A—C2A—H2AA121.0C5B—C4B—C3B121.39 (9)
C1A—C2A—H2AA121.0C5B—C4B—H4BA119.3
C2A—C3A—C4A121.25 (10)C3B—C4B—H4BA119.3
C2A—C3A—C18A116.56 (10)C4B—C5B—C6B116.83 (9)
C4A—C3A—C18A122.16 (10)C4B—C5B—H5BA121.6
C5A—C4A—C3A121.37 (10)C6B—C5B—H5BA121.6
C5A—C4A—H4AA119.3N2B—C6B—C5B132.29 (9)
C3A—C4A—H4AA119.3N2B—C6B—C1B105.45 (8)
C4A—C5A—C6A116.83 (10)C5B—C6B—C1B122.26 (9)
C4A—C5A—H5AA121.6N1B—C7B—N2B112.95 (9)
C6A—C5A—H5AA121.6N1B—C7B—C8B121.16 (9)
N2A—C6A—C5A131.84 (9)N2B—C7B—C8B125.80 (9)
N2A—C6A—C1A105.57 (9)C9B—C8B—C13B117.17 (9)
C5A—C6A—C1A122.57 (9)C9B—C8B—C7B125.50 (9)
N1A—C7A—N2A112.74 (9)C13B—C8B—C7B117.23 (9)
N1A—C7A—C8A122.08 (9)C10B—C9B—C8B121.53 (9)
N2A—C7A—C8A125.06 (9)C10B—C9B—H9BA119.2
C9A—C8A—C13A117.35 (9)C8B—C9B—H9BA119.2
C9A—C8A—C7A124.98 (9)C9B—C10B—C11B121.41 (9)
C13A—C8A—C7A117.60 (9)C9B—C10B—H10B119.3
C10A—C9A—C8A121.31 (9)C11B—C10B—H10B119.3
C10A—C9A—H9AA119.3N4B—C11B—C12B121.47 (9)
C8A—C9A—H9AA119.3N4B—C11B—C10B121.57 (9)
C9A—C10A—C11A121.22 (9)C12B—C11B—C10B116.95 (9)
C9A—C10A—H10A119.4C13B—C12B—C11B121.06 (9)
C11A—C10A—H10A119.4C13B—C12B—H12B119.5
N4A—C11A—C12A120.55 (8)C11B—C12B—H12B119.5
N4A—C11A—C10A122.32 (9)C12B—C13B—C8B121.84 (9)
C12A—C11A—C10A117.11 (9)C12B—C13B—H13B119.1
C13A—C12A—C11A121.23 (9)C8B—C13B—H13B119.1
C13A—C12A—H12A119.4N4B—C14B—C15B111.95 (11)
C11A—C12A—H12A119.4N4B—C14B—H14C109.2
C12A—C13A—C8A121.76 (9)C15B—C14B—H14C109.2
C12A—C13A—H13A119.1N4B—C14B—H14D109.2
C8A—C13A—H13A119.1C15B—C14B—H14D109.2
N4A—C14A—C15A111.56 (9)H14C—C14B—H14D107.9
N4A—C14A—H14A109.3O3B—C15B—C14B111.26 (10)
C15A—C14A—H14A109.3O3B—C15B—H15C109.4
N4A—C14A—H14B109.3C14B—C15B—H15C109.4
C15A—C14A—H14B109.3O3B—C15B—H15D109.4
H14A—C14A—H14B108.0C14B—C15B—H15D109.4
O3A—C15A—C14A111.86 (9)H15C—C15B—H15D108.0
O3A—C15A—H15A109.2O3B—C16B—C17B112.55 (10)
C14A—C15A—H15A109.2O3B—C16B—H16C109.1
O3A—C15A—H15B109.2C17B—C16B—H16C109.1
C14A—C15A—H15B109.2O3B—C16B—H16D109.1
H15A—C15A—H15B107.9C17B—C16B—H16D109.1
O3A—C16A—C17A111.67 (9)H16C—C16B—H16D107.8
O3A—C16A—H16A109.3N4B—C17B—C16B111.15 (9)
C17A—C16A—H16A109.3N4B—C17B—H17C109.4
O3A—C16A—H16B109.3C16B—C17B—H17C109.4
C17A—C16A—H16B109.3N4B—C17B—H17D109.4
H16A—C16A—H16B107.9C16B—C17B—H17D109.4
N4A—C17A—C16A111.41 (9)H17C—C17B—H17D108.0
N4A—C17A—H17A109.3O4B—C18B—O1B123.17 (10)
C16A—C17A—H17A109.3O4B—C18B—O1Y117.7 (3)
N4A—C17A—H17B109.3O4B—C18B—C3B124.04 (10)
C16A—C17A—H17B109.3O1B—C18B—C3B112.70 (9)
H17A—C17A—H17B108.0O1Y—C18B—C3B108.5 (2)
N2A—C21A—C22A109.96 (8)N2B—C21B—C22B110.99 (8)
N2A—C21A—H21A109.7N2B—C21B—H21C109.4
C22A—C21A—H21A109.7C22B—C21B—H21C109.4
N2A—C21A—H21B109.7N2B—C21B—H21D109.4
C22A—C21A—H21B109.7C22B—C21B—H21D109.4
H21A—C21A—H21B108.2H21C—C21B—H21D108.0
N3A—C22A—C21A111.70 (8)N3B—C22B—C21B111.15 (8)
N3A—C22A—H22A109.3N3B—C22B—H22C109.4
C21A—C22A—H22A109.3C21B—C22B—H22C109.4
N3A—C22A—H22B109.3N3B—C22B—H22D109.4
C21A—C22A—H22B109.3C21B—C22B—H22D109.4
H22A—C22A—H22B107.9H22C—C22B—H22D108.0
N3A—C23A—C24A110.02 (10)N3B—C23B—C24B110.39 (8)
N3A—C23A—H23A109.7N3B—C23B—H23C109.6
C24A—C23A—H23A109.7C24B—C23B—H23C109.6
N3A—C23A—H23B109.7N3B—C23B—H23D109.6
C24A—C23A—H23B109.7C24B—C23B—H23D109.6
H23A—C23A—H23B108.2H23C—C23B—H23D108.1
O2A—C24A—C23A111.05 (9)O2B—C24B—C23B111.75 (9)
O2A—C24A—H24A109.4O2B—C24B—H24C109.3
C23A—C24A—H24A109.4C23B—C24B—H24C109.3
O2A—C24A—H24B109.4O2B—C24B—H24D109.3
C23A—C24A—H24B109.4C23B—C24B—H24D109.3
H24A—C24A—H24B108.0H24C—C24B—H24D107.9
O2A—C25A—C26A111.77 (10)O2B—C25B—C26B110.73 (9)
O2A—C25A—H25A109.3O2B—C25B—H25C109.5
C26A—C25A—H25A109.3C26B—C25B—H25C109.5
O2A—C25A—H25B109.3O2B—C25B—H25D109.5
C26A—C25A—H25B109.3C26B—C25B—H25D109.5
H25A—C25A—H25B107.9H25C—C25B—H25D108.1
N3A—C26A—C25A110.20 (10)N3B—C26B—C25B109.40 (9)
N3A—C26A—H26A109.6N3B—C26B—H26C109.8
C25A—C26A—H26A109.6C25B—C26B—H26C109.8
N3A—C26A—H26B109.6N3B—C26B—H26D109.8
C25A—C26A—H26B109.6C25B—C26B—H26D109.8
H26A—C26A—H26B108.1H26C—C26B—H26D108.2
C18A—O1A—C19A—C20A−173.2 (2)C18B—O1B—C19B—C20B−84.92 (15)
C18A—O1X—C19X—C20X86.8 (6)C18B—O1Y—C19Y—C20Y62.4 (10)
C19A—O1A—C18A—O4A−2.7 (3)C7B—N1B—C1B—C2B178.19 (11)
C19A—O1A—C18A—C3A−175.87 (15)C7B—N1B—C1B—C6B−0.64 (12)
C19A—O1A—C18A—O1X111.3 (7)N1B—C1B—C2B—C3B178.37 (11)
C19X—O1X—C18A—O4A10.8 (5)C6B—C1B—C2B—C3B−2.90 (16)
C19X—O1X—C18A—O1A−69.1 (6)C1B—C2B—C3B—C4B1.96 (17)
C19X—O1X—C18A—C3A175.6 (3)C1B—C2B—C3B—C18B−177.72 (10)
C7A—N1A—C1A—C2A−179.42 (12)C2B—C3B—C4B—C5B0.30 (17)
C7A—N1A—C1A—C6A−0.30 (12)C18B—C3B—C4B—C5B179.96 (11)
N1A—C1A—C2A—C3A179.53 (11)C3B—C4B—C5B—C6B−1.57 (16)
C6A—C1A—C2A—C3A0.48 (17)C7B—N2B—C6B—C5B179.54 (11)
C1A—C2A—C3A—C4A−1.01 (18)C21B—N2B—C6B—C5B0.53 (18)
C1A—C2A—C3A—C18A−179.19 (11)C7B—N2B—C6B—C1B−0.75 (11)
O4A—C18A—C3A—C2A5.8 (2)C21B—N2B—C6B—C1B−179.76 (9)
O1A—C18A—C3A—C2A178.74 (15)C4B—C5B—C6B—N2B−179.73 (11)
O1X—C18A—C3A—C2A−159.5 (2)C4B—C5B—C6B—C1B0.60 (16)
O4A—C18A—C3A—C4A−172.36 (15)N1B—C1B—C6B—N2B0.88 (12)
O1A—C18A—C3A—C4A0.6 (2)C2B—C1B—C6B—N2B−178.08 (10)
O1X—C18A—C3A—C4A22.3 (3)N1B—C1B—C6B—C5B−179.37 (10)
C2A—C3A—C4A—C5A0.06 (18)C2B—C1B—C6B—C5B1.67 (16)
C18A—C3A—C4A—C5A178.14 (12)C1B—N1B—C7B—N2B0.16 (12)
C3A—C4A—C5A—C6A1.39 (17)C1B—N1B—C7B—C8B−176.65 (9)
C7A—N2A—C6A—C5A178.15 (12)C6B—N2B—C7B—N1B0.39 (12)
C21A—N2A—C6A—C5A−5.01 (18)C21B—N2B—C7B—N1B179.32 (10)
C7A—N2A—C6A—C1A−0.03 (11)C6B—N2B—C7B—C8B177.01 (10)
C21A—N2A—C6A—C1A176.80 (9)C21B—N2B—C7B—C8B−4.05 (17)
C4A—C5A—C6A—N2A−179.86 (11)N1B—C7B—C8B—C9B−147.51 (11)
C4A—C5A—C6A—C1A−1.94 (17)N2B—C7B—C8B—C9B36.12 (17)
N1A—C1A—C6A—N2A0.21 (12)N1B—C7B—C8B—C13B28.76 (15)
C2A—C1A—C6A—N2A179.42 (10)N2B—C7B—C8B—C13B−147.61 (11)
N1A—C1A—C6A—C5A−178.19 (10)C13B—C8B—C9B—C10B0.67 (16)
C2A—C1A—C6A—C5A1.03 (17)C7B—C8B—C9B—C10B176.94 (10)
C1A—N1A—C7A—N2A0.28 (12)C8B—C9B—C10B—C11B1.19 (17)
C1A—N1A—C7A—C8A176.39 (10)C17B—N4B—C11B—C12B−22.10 (15)
C6A—N2A—C7A—N1A−0.16 (12)C14B—N4B—C11B—C12B−161.06 (11)
C21A—N2A—C7A—N1A−176.76 (10)C17B—N4B—C11B—C10B158.50 (11)
C6A—N2A—C7A—C8A−176.13 (10)C14B—N4B—C11B—C10B19.54 (15)
C21A—N2A—C7A—C8A7.27 (17)C9B—C10B—C11B—N4B177.27 (10)
N1A—C7A—C8A—C9A139.33 (11)C9B—C10B—C11B—C12B−2.15 (16)
N2A—C7A—C8A—C9A−45.05 (16)N4B—C11B—C12B—C13B−178.12 (10)
N1A—C7A—C8A—C13A−37.46 (15)C10B—C11B—C12B—C13B1.30 (16)
N2A—C7A—C8A—C13A138.16 (11)C11B—C12B—C13B—C8B0.53 (17)
C13A—C8A—C9A—C10A0.33 (16)C9B—C8B—C13B—C12B−1.52 (16)
C7A—C8A—C9A—C10A−176.47 (10)C7B—C8B—C13B—C12B−178.11 (10)
C8A—C9A—C10A—C11A−1.16 (16)C11B—N4B—C14B—C15B−172.34 (11)
C14A—N4A—C11A—C12A174.99 (10)C17B—N4B—C14B—C15B47.20 (15)
C17A—N4A—C11A—C12A37.80 (14)C16B—O3B—C15B—C14B61.40 (16)
C14A—N4A—C11A—C10A−6.41 (15)N4B—C14B—C15B—O3B−54.87 (18)
C17A—N4A—C11A—C10A−143.60 (11)C15B—O3B—C16B—C17B−61.80 (14)
C9A—C10A—C11A—N4A−177.58 (10)C11B—N4B—C17B—C16B173.03 (10)
C9A—C10A—C11A—C12A1.07 (15)C14B—N4B—C17B—C16B−46.42 (14)
N4A—C11A—C12A—C13A178.48 (10)O3B—C16B—C17B—N4B54.58 (14)
C10A—C11A—C12A—C13A−0.19 (16)C19B—O1B—C18B—O4B−1.2 (2)
C11A—C12A—C13A—C8A−0.63 (17)C19B—O1B—C18B—O1Y91.5 (4)
C9A—C8A—C13A—C12A0.56 (16)C19B—O1B—C18B—C3B−177.84 (11)
C7A—C8A—C13A—C12A177.60 (10)C19Y—O1Y—C18B—O4B26.3 (8)
C11A—N4A—C14A—C15A174.35 (9)C19Y—O1Y—C18B—O1B−83.0 (7)
C17A—N4A—C14A—C15A−47.14 (13)C19Y—O1Y—C18B—C3B173.6 (6)
C16A—O3A—C15A—C14A−60.93 (13)C2B—C3B—C18B—O4B−16.55 (19)
N4A—C14A—C15A—O3A54.02 (14)C4B—C3B—C18B—O4B163.78 (13)
C15A—O3A—C16A—C17A61.79 (12)C2B—C3B—C18B—O1B160.06 (11)
C11A—N4A—C17A—C16A−173.12 (9)C4B—C3B—C18B—O1B−19.62 (17)
C14A—N4A—C17A—C16A47.94 (13)C2B—C3B—C18B—O1Y−161.3 (3)
O3A—C16A—C17A—N4A−55.71 (13)C4B—C3B—C18B—O1Y19.0 (4)
C6A—N2A—C21A—C22A−75.87 (12)C6B—N2B—C21B—C22B83.50 (12)
C7A—N2A—C21A—C22A100.20 (12)C7B—N2B—C21B—C22B−95.26 (12)
C23A—N3A—C22A—C21A−154.95 (9)C26B—N3B—C22B—C21B−145.67 (9)
C26A—N3A—C22A—C21A82.78 (11)C23B—N3B—C22B—C21B91.46 (10)
N2A—C21A—C22A—N3A−177.11 (8)N2B—C21B—C22B—N3B−174.05 (8)
C22A—N3A—C23A—C24A178.76 (9)C22B—N3B—C23B—C24B−177.62 (9)
C26A—N3A—C23A—C24A−57.54 (12)C26B—N3B—C23B—C24B57.15 (11)
C25A—O2A—C24A—C23A−58.52 (13)C25B—O2B—C24B—C23B57.38 (12)
N3A—C23A—C24A—O2A59.31 (14)N3B—C23B—C24B—O2B−57.12 (12)
C24A—O2A—C25A—C26A57.69 (14)C24B—O2B—C25B—C26B−58.85 (12)
C22A—N3A—C26A—C25A−179.66 (10)C22B—N3B—C26B—C25B177.08 (8)
C23A—N3A—C26A—C25A56.43 (13)C23B—N3B—C26B—C25B−58.59 (11)
O2A—C25A—C26A—N3A−57.24 (14)O2B—C25B—C26B—N3B60.28 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14B—H14D···O4Ai0.992.393.1322 (17)132
C16B—H16C···O1Bii0.992.423.2944 (15)147
C17B—H17C···O3Aiii0.992.603.4963 (18)151
C23B—H23D···O2Aiv0.992.533.3839 (16)144
C24B—H24D···N1Bv0.992.613.4668 (14)145
C25B—H25C···N3A0.992.613.5189 (18)153

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y−1/2, −z+3/2; (iii) x−1, y−1, z; (iv) x−1, y, z; (v) −x, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2728).

References

  • Bruker (2009). APEX2, SAINT and SADABSBruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Haugwitz, R. D. (1982). J. Med. Chem. 25, 969–974. [PubMed]
  • Hisano, T. (1982). Chem. Pharm. Bull. 30, 2996–3004.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Vijaya, B. R., Rajeev, K. S., Varadaraj, B. G. & Gautham, G. S. (2009). Asian J. Res. Chem. 2, 162–167.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography