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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o66–o67.
Published online 2008 December 10. doi:  10.1107/S1600536808039081
PMCID: PMC2967978

4-[(5-Hydr­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)phenyl­meth­yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol hemisolvate

Abstract

The asymmetric unit of the title compound, C27H24N4O2·0.5C2H6O, comprises two crystallographically independent mol­ecules (A and B) with slightly different conformations, and one ethanol mol­ecule of crystallization. Intra­molecular C—H(...)O and O—H(...)O hydrogen bonds generate six- and eight-membered rings, producing S(6) and S(8) ring motifs, respectively. In mol­ecule A, one of the benzene rings is disordered over two positions, with site-occupancy factors of 0.542 (11) and 0.458 (11). The dihedral angles between the central benzene ring and the two outer benzene rings are 73.88 (9) and 82.6 (2)/88.9 (2)° in mol­ecule A, and 80.81 (8) and 79.38 (8)° in mol­ecule B. In the crystal structure, mol­ecules form infinite one-dimensional chains in the (101) plane. The crystal structure is stabilized by inter­molecular O—H(...)N, N—H(...)N, N—H(...)O and C—H(...)O hydrogen bonds, weak C—H(...)π and π–π [centroid–centroid = 3.5496 (1) Å] inter­actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For details of the biological activity of pyrazole derivatives, see: Burger & Iorio (1979 [triangle], 1980 [triangle]); Kalluraya & Ramesh (2001 [triangle]); Holla et al. (1994 [triangle]); Windholz (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00o66-scheme1.jpg

Experimental

Crystal data

  • C27H24N4O2·0.5C2H6O
  • M r = 459.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o66-efi1.jpg
  • a = 8.3767 (2) Å
  • b = 13.9498 (3) Å
  • c = 20.4797 (4) Å
  • α = 101.074 (1)°
  • β = 93.723 (1)°
  • γ = 93.579 (1)°
  • V = 2336.74 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100.0 (1) K
  • 0.38 × 0.26 × 0.17 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.960, T max = 0.986
  • 41677 measured reflections
  • 13462 independent reflections
  • 9482 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.161
  • S = 1.03
  • 13462 reflections
  • 632 parameters
  • 42 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); 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, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039081/sj2553sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039081/sj2553Isup2.hkl

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

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Pyrazole derivatives are reported to possess varied biological activities such as anti-inflammatory (Windholz 2003), analgesic (Windholz 2003), hypoglysemic, seditive (Burger et al., 1979), hypnotic (Burger et al., 1980), antifungal and antibacterial (Kalluraya et al., 2001) activities. Propenones are also found to show good antibacterial activity (Holla et al. 1994). Prompted by these observations, we planned to synthesize propenones containing pyrazole moiety and we report here the structure of the title compound, I, Fig. 1.

The bond lengths (Allen et al., 1987) and angles in the title compound have normal values. The asymmetric unit of the title compound, is composed of two crystallographically independent molecules (A and B) with slightly different conformations and one ethanol molecule of crystallization. Intramolecular C—H···O and O—H···O hydrogen bonds generate six- and eight-membered rings, producing S(6) and S(8) ring motifs (Bernstein et al. 1995), respectively. In molecule A, one of the benzene rings is disordered over two positions with the site-occupancy factors 0.542 (11)/0.458 (11). The dihedral angles between the central benzene ring and the two outer benzene rings are 73.88 (9) and 82.6 (2)/88.9 (2)° in molecule A; and 80.81 (8) and 79.38 (8)° in molecule B, respectively. In the crystal structure, molecules are linked into infinite 1-dimensional chains in the (101)-plane (Fig. 2). The crystal structure is stabilized by intermolecular O—H···N, N—H···N, N—H···O, and C—H···O hydrogen bonds, weak C—H···π (Table 1, Cg1 and Cg2 are the centroids of the C11A–C16A and C20C–C25C benzene rings respectively) and π-π interactions [Cg3···Cg4 = 3.5496 (10) Å; symmetry code: -1 + x,-1 + y, z; Cg3 and Cg4 are the centroids of the C1A–C6A and N1B/N2B/C7B–C9B benzene rings respectively].

Experimental

The title compound was prepared by the direct fusion of 1-phenyl- 3-methyl 5-pyrazolone (0.1 mole) with benzaldehyde (0.1 mole) at 413 K for 3 h. The reaction mixture was cooled to room temperature and stirred with methanol using a glass rod. The mixture was then filtered to obtain a solid product. Single crystals suitable for X-ray analysis were obtained by recrystallization from ethanol under slow evaporation (m.p. 351–353 K).

Refinement

N-bonded H atoms were located from the difference Fourier map and freely refined. H atoms of the hydroxy groups were positioned with freely rotating O—H bonds and constrained with a fixed distance of 0.82 Å. Other hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied to the methyl hydrogen atoms. One of the benzene rings in molecule A is disordered over two positions with site-occupancy factors 0.542 (11)/0.458 (11). The disorder was modeled based on a rigid bond model and the C atoms refined isotropically.

Figures

Fig. 1.
The molecular structure of (I) with atom labels and 40% probability ellipsoids for non-H atoms. For clarity, only the hydrogen atoms involved in the hydrogen bonding and the hydrogen of the ethanol molecule are shown. Intramolecular interactions are shown ...
Fig. 2.
The crystal packing of the major disorder component of (I), showing the infinite 1-dimensional chains along (1 0 1). Intermolecular interactions are shown as dashed lines.

Crystal data

C27H24N4O2·0.5C2H6OZ = 4
Mr = 459.54F(000) = 972
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Melting point: 352 K
a = 8.3767 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.9498 (3) ÅCell parameters from 8872 reflections
c = 20.4797 (4) Åθ = 2.5–31.5°
α = 101.074 (1)°µ = 0.09 mm1
β = 93.723 (1)°T = 100 K
γ = 93.579 (1)°Block, yellow
V = 2336.74 (9) Å30.38 × 0.26 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer13462 independent reflections
Radiation source: fine-focus sealed tube9482 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −11→11
Tmin = 0.960, Tmax = 0.986k = −19→19
41677 measured reflectionsl = −26→28

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0833P)2 + 0.5342P] where P = (Fo2 + 2Fc2)/3
13462 reflections(Δ/σ)max < 0.001
632 parametersΔρmax = 0.40 e Å3
42 restraintsΔρmin = −0.43 e Å3

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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)
O1A0.04693 (14)0.06678 (8)0.31199 (5)0.0191 (2)
O2A0.06851 (15)0.10931 (9)0.44047 (6)0.0228 (3)
H2OA0.05340.09420.39970.034*
N1A0.15609 (16)0.11331 (10)0.22035 (6)0.0160 (3)
N2A0.21144 (16)0.20043 (10)0.20320 (7)0.0164 (3)
N3A0.30731 (16)0.31761 (10)0.52500 (7)0.0186 (3)
N4A0.24860 (16)0.22036 (10)0.51385 (7)0.0173 (3)
C20A0.3120 (10)0.1609 (6)0.5553 (5)0.021 (2)*0.542 (11)
C21A0.3284 (6)0.0608 (3)0.5268 (2)0.0232 (10)*0.542 (11)
H21A0.29840.03690.48180.028*0.542 (11)
C22A0.3892 (7)−0.0009 (3)0.5663 (2)0.0322 (11)*0.542 (11)
H22A0.3934−0.06700.54800.039*0.542 (11)
C23A0.4433 (7)0.0336 (4)0.6317 (3)0.0304 (13)*0.542 (11)
H23A0.4779−0.00890.65860.036*0.542 (11)
C24A0.4451 (8)0.1300 (4)0.6562 (3)0.0352 (16)*0.542 (11)
H24A0.48840.15520.69950.042*0.542 (11)
C25A0.3826 (7)0.1931 (4)0.6171 (3)0.0305 (16)*0.542 (11)
H25A0.39030.26000.63470.037*0.542 (11)
C20C0.3025 (11)0.1530 (7)0.5557 (5)0.016 (2)*0.458 (11)
C21C0.2784 (8)0.0544 (4)0.5377 (3)0.0301 (13)*0.458 (11)
H21C0.22260.02620.49710.036*0.458 (11)
C22C0.3367 (8)−0.0048 (3)0.5795 (3)0.0282 (13)*0.458 (11)
H22C0.3235−0.07260.56630.034*0.458 (11)
C23C0.4148 (7)0.0373 (4)0.6411 (3)0.0186 (11)*0.458 (11)
H23C0.4637−0.00130.66760.022*0.458 (11)
C24C0.4187 (7)0.1381 (4)0.6624 (3)0.0146 (11)*0.458 (11)
H24C0.46450.16600.70490.018*0.458 (11)
C25C0.3572 (7)0.1980 (4)0.6228 (3)0.0134 (12)*0.458 (11)
H25C0.35140.26460.63870.016*0.458 (11)
C1A0.25204 (19)−0.05002 (12)0.20784 (9)0.0205 (3)
H1AA0.2910−0.03620.25250.025*
C2A0.2680 (2)−0.14120 (13)0.16831 (10)0.0252 (4)
H2AA0.3177−0.18860.18680.030*
C3A0.2111 (2)−0.16232 (13)0.10179 (9)0.0247 (4)
H3AA0.2225−0.22350.07570.030*
C4A0.1370 (2)−0.09156 (13)0.07439 (9)0.0259 (4)
H4AA0.0992−0.10530.02960.031*
C5A0.1188 (2)−0.00035 (13)0.11323 (8)0.0218 (3)
H5AA0.06790.04670.09480.026*
C6A0.17717 (18)0.02021 (12)0.17991 (8)0.0159 (3)
C7A0.09891 (18)0.13337 (12)0.28245 (7)0.0150 (3)
C8A0.11043 (17)0.23705 (11)0.30291 (7)0.0142 (3)
C9A0.17638 (18)0.27454 (12)0.25245 (8)0.0156 (3)
C10A0.04788 (18)0.29225 (12)0.36615 (7)0.0147 (3)
H10A0.06380.36190.36430.018*
C11A−0.13429 (18)0.27032 (11)0.36632 (8)0.0150 (3)
C12A−0.23042 (19)0.24023 (13)0.30674 (8)0.0200 (3)
H12A−0.18300.23030.26640.024*
C13A−0.3961 (2)0.22486 (14)0.30669 (9)0.0242 (4)
H13A−0.45830.20410.26660.029*
C14A−0.4685 (2)0.24037 (14)0.36616 (9)0.0253 (4)
H14A−0.57920.23010.36630.030*
C15A−0.3747 (2)0.27133 (15)0.42537 (9)0.0258 (4)
H15A−0.42310.28270.46540.031*
C16A−0.2086 (2)0.28570 (13)0.42591 (8)0.0209 (3)
H16A−0.14710.30570.46630.025*
C17A0.14073 (18)0.28029 (12)0.42951 (7)0.0153 (3)
C18A0.24186 (18)0.35227 (12)0.47389 (8)0.0170 (3)
C19A0.14672 (19)0.19775 (12)0.45748 (8)0.0168 (3)
C26A0.2124 (2)0.37793 (13)0.24580 (9)0.0249 (4)
H26A0.27910.37950.20960.037*
H26B0.26730.41430.28650.037*
H26C0.11400.40670.23710.037*
C27A0.2781 (2)0.45637 (13)0.46862 (9)0.0262 (4)
H27A0.33840.49080.50860.039*
H27B0.17950.48650.46290.039*
H27C0.33970.45880.43100.039*
O2B0.93942 (14)0.63369 (8)0.04138 (6)0.0179 (2)
H2OB0.92720.64400.08150.027*
O1B0.91354 (13)0.66225 (8)0.16426 (5)0.0182 (2)
N4B0.90424 (15)0.71344 (10)−0.04759 (6)0.0150 (3)
N3B0.81223 (16)0.78239 (10)−0.06849 (7)0.0170 (3)
N2B0.88285 (17)0.89755 (11)0.25148 (7)0.0190 (3)
N1B0.94837 (16)0.80809 (10)0.24321 (7)0.0173 (3)
C1B1.1437 (2)0.70528 (14)0.28164 (9)0.0243 (4)
H1BA1.14680.67100.23810.029*
C2B1.2358 (2)0.68007 (16)0.33339 (9)0.0314 (4)
H2BA1.30020.62780.32470.038*
C3B1.2329 (2)0.73225 (17)0.39840 (9)0.0339 (5)
H3BA1.29540.71490.43290.041*
C4B1.1377 (2)0.80951 (16)0.41180 (9)0.0306 (4)
H4BA1.13670.84440.45530.037*
C5B1.0431 (2)0.83566 (14)0.36065 (8)0.0233 (4)
H5BA0.97850.88770.36960.028*
C6B1.04641 (19)0.78271 (13)0.29578 (8)0.0196 (3)
C7B0.87984 (18)0.74959 (12)0.18494 (8)0.0157 (3)
C8B0.76814 (18)0.80655 (11)0.15665 (7)0.0147 (3)
C9B0.77990 (19)0.89732 (12)0.19769 (8)0.0172 (3)
C10B0.65481 (18)0.76875 (11)0.09613 (7)0.0142 (3)
H10B0.58280.82090.09360.017*
C11B0.54597 (17)0.67919 (11)0.10342 (8)0.0137 (3)
C12B0.45406 (19)0.62474 (12)0.04803 (8)0.0186 (3)
H12B0.46460.64040.00630.022*
C13B0.3471 (2)0.54760 (13)0.05414 (9)0.0227 (3)
H13B0.28580.51250.01670.027*
C14B0.3314 (2)0.52257 (13)0.11590 (9)0.0217 (3)
H14B0.26030.47040.11990.026*
C15B0.42219 (19)0.57569 (12)0.17175 (8)0.0190 (3)
H15B0.41230.55910.21320.023*
C16B0.52806 (18)0.65393 (12)0.16558 (8)0.0163 (3)
H16B0.58760.68980.20320.020*
C17B0.73824 (18)0.75532 (11)0.03188 (8)0.0142 (3)
C18B0.71295 (19)0.80612 (12)−0.02041 (8)0.0160 (3)
C19B0.86207 (18)0.69663 (11)0.01323 (7)0.0140 (3)
C20B1.04430 (18)0.68613 (12)−0.08021 (7)0.0154 (3)
C21B1.09192 (19)0.59116 (12)−0.08653 (8)0.0183 (3)
H21B1.03160.5441−0.07010.022*
C22B1.2306 (2)0.56752 (13)−0.11770 (8)0.0216 (3)
H22B1.26330.5043−0.12200.026*
C23B1.3209 (2)0.63729 (13)−0.14245 (8)0.0221 (3)
H23B1.41390.6208−0.16310.027*
C24B1.2724 (2)0.73159 (13)−0.13640 (8)0.0211 (3)
H24B1.33270.7783−0.15310.025*
C25B1.13422 (19)0.75638 (12)−0.10552 (8)0.0190 (3)
H25B1.10150.8196−0.10170.023*
C26B0.7042 (2)0.98896 (12)0.19062 (9)0.0231 (4)
H26D0.70491.03100.23370.035*
H26E0.59550.97300.17190.035*
H26F0.76331.02190.16170.035*
C27B0.5924 (2)0.87954 (13)−0.02620 (9)0.0232 (4)
H27D0.59400.8972−0.06920.035*
H27E0.61850.93690.00800.035*
H27F0.48730.8516−0.02110.035*
C280.8096 (3)0.54578 (19)0.31209 (13)0.0480 (6)
H28A0.88870.50140.29700.072*
H28B0.85530.59380.34980.072*
H28C0.77540.57800.27680.072*
C290.6683 (3)0.48982 (15)0.33204 (10)0.0331 (4)
H29A0.62450.44040.29400.040*
H29B0.70430.45630.36700.040*
O30.54565 (15)0.54997 (10)0.35503 (7)0.0291 (3)
H30.58030.58970.38860.044*
H2NA0.208 (3)0.2048 (18)0.1585 (13)0.048 (7)*
H2NB0.944 (3)0.9543 (17)0.2753 (11)0.035 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0252 (6)0.0155 (6)0.0156 (5)−0.0042 (5)0.0035 (5)0.0021 (4)
O2A0.0316 (7)0.0195 (6)0.0155 (5)−0.0062 (5)−0.0026 (5)0.0028 (5)
N1A0.0195 (6)0.0140 (6)0.0144 (6)0.0000 (5)0.0034 (5)0.0020 (5)
N2A0.0203 (6)0.0152 (7)0.0145 (6)0.0016 (5)0.0046 (5)0.0035 (5)
N3A0.0175 (6)0.0184 (7)0.0180 (6)−0.0009 (5)−0.0008 (5)0.0005 (5)
N4A0.0181 (6)0.0175 (7)0.0152 (6)0.0011 (5)−0.0005 (5)0.0011 (5)
C1A0.0178 (7)0.0225 (9)0.0215 (8)0.0052 (7)0.0031 (6)0.0037 (7)
C2A0.0239 (8)0.0207 (9)0.0336 (10)0.0092 (7)0.0087 (7)0.0073 (7)
C3A0.0228 (8)0.0182 (9)0.0319 (9)0.0005 (7)0.0112 (7)−0.0011 (7)
C4A0.0301 (9)0.0243 (9)0.0203 (8)0.0011 (8)0.0024 (7)−0.0029 (7)
C5A0.0259 (8)0.0190 (8)0.0202 (8)0.0044 (7)0.0007 (7)0.0028 (7)
C6A0.0150 (7)0.0153 (8)0.0169 (7)0.0017 (6)0.0044 (6)0.0005 (6)
C7A0.0125 (6)0.0186 (8)0.0132 (7)0.0001 (6)0.0007 (5)0.0015 (6)
C8A0.0116 (6)0.0163 (8)0.0140 (7)−0.0004 (6)0.0008 (5)0.0018 (6)
C9A0.0145 (7)0.0175 (8)0.0146 (7)0.0018 (6)0.0004 (6)0.0024 (6)
C10A0.0149 (7)0.0146 (7)0.0140 (7)0.0003 (6)0.0023 (6)0.0012 (6)
C11A0.0140 (7)0.0150 (7)0.0163 (7)0.0032 (6)0.0013 (6)0.0029 (6)
C12A0.0173 (7)0.0241 (9)0.0172 (7)0.0036 (7)0.0013 (6)−0.0001 (6)
C13A0.0159 (7)0.0292 (10)0.0252 (9)0.0031 (7)−0.0030 (7)0.0004 (7)
C14A0.0134 (7)0.0343 (10)0.0304 (9)0.0041 (7)0.0031 (7)0.0103 (8)
C15A0.0172 (8)0.0416 (11)0.0222 (8)0.0082 (8)0.0068 (7)0.0119 (8)
C16A0.0177 (7)0.0298 (9)0.0164 (7)0.0057 (7)0.0024 (6)0.0057 (7)
C17A0.0143 (7)0.0178 (8)0.0127 (7)0.0009 (6)0.0023 (6)0.0003 (6)
C18A0.0144 (7)0.0197 (8)0.0152 (7)0.0006 (6)0.0011 (6)−0.0008 (6)
C19A0.0175 (7)0.0182 (8)0.0132 (7)−0.0004 (6)0.0017 (6)−0.0002 (6)
C26A0.0349 (10)0.0205 (9)0.0203 (8)−0.0006 (7)0.0078 (7)0.0051 (7)
C27A0.0297 (9)0.0231 (9)0.0232 (8)−0.0042 (7)−0.0053 (7)0.0024 (7)
O2B0.0235 (6)0.0172 (6)0.0145 (5)0.0064 (5)0.0033 (5)0.0046 (4)
O1B0.0213 (6)0.0160 (6)0.0165 (5)0.0032 (5)−0.0001 (4)0.0013 (4)
N4B0.0165 (6)0.0145 (6)0.0146 (6)0.0041 (5)0.0031 (5)0.0030 (5)
N3B0.0188 (6)0.0170 (7)0.0163 (6)0.0050 (5)0.0023 (5)0.0048 (5)
N2B0.0200 (7)0.0140 (7)0.0202 (7)−0.0016 (5)0.0006 (6)−0.0026 (5)
N1B0.0176 (6)0.0163 (7)0.0160 (6)−0.0006 (5)−0.0005 (5)−0.0008 (5)
C1B0.0206 (8)0.0336 (10)0.0181 (8)0.0023 (7)0.0009 (6)0.0038 (7)
C2B0.0243 (9)0.0463 (12)0.0251 (9)0.0097 (9)0.0001 (7)0.0089 (9)
C3B0.0262 (9)0.0558 (14)0.0207 (9)0.0038 (9)−0.0029 (7)0.0116 (9)
C4B0.0295 (9)0.0453 (12)0.0144 (8)−0.0051 (9)0.0007 (7)0.0020 (8)
C5B0.0227 (8)0.0281 (9)0.0172 (8)−0.0033 (7)0.0026 (7)0.0010 (7)
C6B0.0158 (7)0.0265 (9)0.0158 (7)−0.0043 (6)0.0001 (6)0.0049 (7)
C7B0.0163 (7)0.0164 (8)0.0133 (7)−0.0023 (6)0.0025 (6)0.0005 (6)
C8B0.0157 (7)0.0147 (7)0.0130 (7)−0.0008 (6)0.0027 (6)0.0009 (6)
C9B0.0157 (7)0.0177 (8)0.0176 (7)−0.0009 (6)0.0050 (6)0.0018 (6)
C10B0.0147 (7)0.0141 (7)0.0139 (7)0.0022 (6)0.0024 (6)0.0016 (6)
C11B0.0116 (6)0.0128 (7)0.0164 (7)0.0023 (6)0.0025 (5)0.0010 (6)
C12B0.0198 (7)0.0189 (8)0.0165 (7)−0.0008 (6)−0.0003 (6)0.0037 (6)
C13B0.0201 (8)0.0226 (9)0.0231 (8)−0.0047 (7)−0.0045 (7)0.0026 (7)
C14B0.0176 (7)0.0195 (9)0.0282 (9)−0.0039 (6)0.0003 (7)0.0072 (7)
C15B0.0184 (7)0.0205 (8)0.0190 (8)0.0022 (6)0.0042 (6)0.0053 (6)
C16B0.0160 (7)0.0168 (8)0.0154 (7)0.0021 (6)0.0020 (6)0.0010 (6)
C17B0.0134 (6)0.0131 (7)0.0158 (7)0.0002 (6)0.0008 (6)0.0025 (6)
C18B0.0165 (7)0.0151 (8)0.0160 (7)0.0007 (6)0.0007 (6)0.0025 (6)
C19B0.0153 (7)0.0124 (7)0.0134 (7)−0.0011 (6)0.0011 (6)0.0009 (6)
C20B0.0157 (7)0.0177 (8)0.0120 (7)0.0021 (6)0.0006 (6)0.0009 (6)
C21B0.0193 (7)0.0160 (8)0.0185 (7)0.0009 (6)0.0015 (6)0.0006 (6)
C22B0.0212 (8)0.0220 (9)0.0220 (8)0.0075 (7)0.0036 (7)0.0024 (7)
C23B0.0190 (8)0.0286 (9)0.0186 (8)0.0050 (7)0.0036 (6)0.0024 (7)
C24B0.0192 (8)0.0255 (9)0.0197 (8)0.0007 (7)0.0032 (6)0.0072 (7)
C25B0.0199 (7)0.0174 (8)0.0198 (8)0.0026 (6)0.0017 (6)0.0036 (6)
C26B0.0252 (8)0.0162 (8)0.0262 (9)0.0015 (7)0.0026 (7)−0.0006 (7)
C27B0.0229 (8)0.0281 (9)0.0216 (8)0.0107 (7)0.0034 (7)0.0088 (7)
C280.0409 (12)0.0560 (16)0.0466 (13)0.0062 (11)0.0164 (11)0.0035 (12)
C290.0431 (11)0.0272 (10)0.0292 (10)0.0105 (9)0.0053 (9)0.0025 (8)
O30.0254 (6)0.0281 (7)0.0295 (7)0.0029 (6)−0.0028 (5)−0.0038 (6)

Geometric parameters (Å, °)

O1A—C7A1.2720 (19)C27A—H27B0.9600
O2A—C19A1.333 (2)C27A—H27C0.9600
O2A—H2OA0.8200O2B—C19B1.3191 (18)
N1A—C7A1.3727 (19)O2B—H2OB0.8200
N1A—N2A1.3892 (18)O1B—C7B1.2664 (19)
N1A—C6A1.428 (2)N4B—C19B1.3749 (19)
N2A—C9A1.359 (2)N4B—N3B1.3821 (17)
N2A—H2NA0.93 (3)N4B—C20B1.4240 (19)
N3A—C18A1.335 (2)N3B—C18B1.3366 (19)
N3A—N4A1.3848 (19)N2B—C9B1.354 (2)
N4A—C19A1.363 (2)N2B—N1B1.3798 (19)
N4A—C20A1.400 (9)N2B—H2NB0.95 (2)
N4A—C20C1.461 (10)N1B—C7B1.378 (2)
C20A—C25A1.344 (11)N1B—C6B1.424 (2)
C20A—C21A1.424 (9)C1B—C2B1.383 (2)
C21A—C22A1.386 (5)C1B—C6B1.391 (2)
C21A—H21A0.9300C1B—H1BA0.9300
C22A—C23A1.371 (6)C2B—C3B1.392 (3)
C22A—H22A0.9300C2B—H2BA0.9300
C23A—C24A1.339 (8)C3B—C4B1.376 (3)
C23A—H23A0.9300C3B—H3BA0.9300
C24A—C25A1.401 (8)C4B—C5B1.391 (3)
C24A—H24A0.9300C4B—H4BA0.9300
C25A—H25A0.9300C5B—C6B1.394 (2)
C20C—C21C1.353 (10)C5B—H5BA0.9300
C20C—C25C1.428 (11)C7B—C8B1.429 (2)
C21C—C22C1.386 (6)C8B—C9B1.373 (2)
C21C—H21C0.9300C8B—C10B1.500 (2)
C22C—C23C1.387 (7)C9B—C26B1.489 (2)
C22C—H22C0.9300C10B—C17B1.515 (2)
C23C—C24C1.388 (7)C10B—C11B1.537 (2)
C23C—H23C0.9300C10B—H10B0.9800
C24C—C25C1.372 (7)C11B—C12B1.392 (2)
C24C—H24C0.9300C11B—C16B1.399 (2)
C25C—H25C0.9300C12B—C13B1.386 (2)
C1A—C6A1.388 (2)C12B—H12B0.9300
C1A—C2A1.390 (2)C13B—C14B1.387 (2)
C1A—H1AA0.9300C13B—H13B0.9300
C2A—C3A1.384 (3)C14B—C15B1.388 (2)
C2A—H2AA0.9300C14B—H14B0.9300
C3A—C4A1.385 (3)C15B—C16B1.393 (2)
C3A—H3AA0.9300C15B—H15B0.9300
C4A—C5A1.388 (2)C16B—H16B0.9300
C4A—H4AA0.9300C17B—C19B1.389 (2)
C5A—C6A1.390 (2)C17B—C18B1.405 (2)
C5A—H5AA0.9300C18B—C27B1.498 (2)
C7A—C8A1.422 (2)C20B—C21B1.392 (2)
C8A—C9A1.376 (2)C20B—C25B1.396 (2)
C8A—C10A1.517 (2)C21B—C22B1.389 (2)
C9A—C26A1.489 (2)C21B—H21B0.9300
C10A—C17A1.512 (2)C22B—C23B1.387 (2)
C10A—C11A1.538 (2)C22B—H22B0.9300
C10A—H10A0.9800C23B—C24B1.386 (2)
C11A—C16A1.392 (2)C23B—H23B0.9300
C11A—C12A1.395 (2)C24B—C25B1.386 (2)
C12A—C13A1.391 (2)C24B—H24B0.9300
C12A—H12A0.9300C25B—H25B0.9300
C13A—C14A1.381 (2)C26B—H26D0.9600
C13A—H13A0.9300C26B—H26E0.9600
C14A—C15A1.381 (3)C26B—H26F0.9600
C14A—H14A0.9300C27B—H27D0.9600
C15A—C16A1.392 (2)C27B—H27E0.9600
C15A—H15A0.9300C27B—H27F0.9600
C16A—H16A0.9300C28—C291.499 (3)
C17A—C19A1.383 (2)C28—H28A0.9600
C17A—C18A1.412 (2)C28—H28B0.9600
C18A—C27A1.491 (2)C28—H28C0.9600
C26A—H26A0.9600C29—O31.414 (2)
C26A—H26B0.9600C29—H29A0.9700
C26A—H26C0.9600C29—H29B0.9700
C27A—H27A0.9600O3—H30.8200
C19A—O2A—H2OA109.5H27A—C27A—H27B109.5
C7A—N1A—N2A109.22 (13)C18A—C27A—H27C109.5
C7A—N1A—C6A128.56 (13)H27A—C27A—H27C109.5
N2A—N1A—C6A121.86 (12)H27B—C27A—H27C109.5
C9A—N2A—N1A107.11 (12)C19B—O2B—H2OB109.5
C9A—N2A—H2NA123.4 (15)C19B—N4B—N3B110.75 (12)
N1A—N2A—H2NA119.1 (15)C19B—N4B—C20B127.71 (13)
C18A—N3A—N4A104.78 (13)N3B—N4B—C20B119.94 (12)
C19A—N4A—N3A110.62 (13)C18B—N3B—N4B104.91 (12)
C19A—N4A—C20A131.0 (4)C9B—N2B—N1B108.23 (13)
N3A—N4A—C20A118.0 (4)C9B—N2B—H2NB123.5 (13)
C19A—N4A—C20C126.9 (4)N1B—N2B—H2NB119.7 (13)
N3A—N4A—C20C122.3 (4)C7B—N1B—N2B108.79 (13)
C20A—N4A—C20C4.7 (7)C7B—N1B—C6B129.47 (14)
C25A—C20A—N4A125.2 (7)N2B—N1B—C6B120.72 (13)
C25A—C20A—C21A115.9 (7)C2B—C1B—C6B118.92 (17)
N4A—C20A—C21A118.0 (7)C2B—C1B—H1BA120.5
C22A—C21A—C20A119.9 (5)C6B—C1B—H1BA120.5
C22A—C21A—H21A120.1C1B—C2B—C3B120.51 (18)
C20A—C21A—H21A120.1C1B—C2B—H2BA119.7
C23A—C22A—C21A121.3 (4)C3B—C2B—H2BA119.7
C23A—C22A—H22A119.4C4B—C3B—C2B120.17 (18)
C21A—C22A—H22A119.4C4B—C3B—H3BA119.9
C24A—C23A—C22A118.5 (5)C2B—C3B—H3BA119.9
C24A—C23A—H23A120.7C3B—C4B—C5B120.34 (17)
C22A—C23A—H23A120.7C3B—C4B—H4BA119.8
C23A—C24A—C25A120.7 (5)C5B—C4B—H4BA119.8
C23A—C24A—H24A119.6C4B—C5B—C6B119.04 (17)
C25A—C24A—H24A119.6C4B—C5B—H5BA120.5
C20A—C25A—C24A122.6 (6)C6B—C5B—H5BA120.5
C20A—C25A—H25A118.7C1B—C6B—C5B121.02 (16)
C24A—C25A—H25A118.7C1B—C6B—N1B119.51 (15)
C21C—C20C—C25C120.5 (7)C5B—C6B—N1B119.47 (15)
C21C—C20C—N4A123.6 (7)O1B—C7B—N1B123.73 (14)
C25C—C20C—N4A115.0 (7)O1B—C7B—C8B129.79 (15)
C20C—C21C—C22C120.2 (6)N1B—C7B—C8B106.47 (13)
C20C—C21C—H21C119.9C9B—C8B—C7B106.70 (14)
C22C—C21C—H21C119.9C9B—C8B—C10B128.39 (14)
C21C—C22C—C23C119.9 (4)C7B—C8B—C10B124.80 (14)
C21C—C22C—H22C120.1N2B—C9B—C8B109.63 (14)
C23C—C22C—H22C120.1N2B—C9B—C26B119.35 (15)
C22C—C23C—C24C118.8 (4)C8B—C9B—C26B131.00 (15)
C22C—C23C—H23C120.6C8B—C10B—C17B112.66 (12)
C24C—C23C—H23C120.6C8B—C10B—C11B112.68 (12)
C25C—C24C—C23C122.1 (5)C17B—C10B—C11B114.10 (13)
C25C—C24C—H24C119.0C8B—C10B—H10B105.5
C23C—C24C—H24C119.0C17B—C10B—H10B105.5
C24C—C25C—C20C116.8 (6)C11B—C10B—H10B105.5
C24C—C25C—H25C121.6C12B—C11B—C16B118.29 (14)
C20C—C25C—H25C121.6C12B—C11B—C10B119.94 (13)
C6A—C1A—C2A119.20 (16)C16B—C11B—C10B121.63 (14)
C6A—C1A—H1AA120.4C13B—C12B—C11B121.02 (15)
C2A—C1A—H1AA120.4C13B—C12B—H12B119.5
C3A—C2A—C1A120.86 (16)C11B—C12B—H12B119.5
C3A—C2A—H2AA119.6C12B—C13B—C14B120.23 (16)
C1A—C2A—H2AA119.6C12B—C13B—H13B119.9
C2A—C3A—C4A119.44 (16)C14B—C13B—H13B119.9
C2A—C3A—H3AA120.3C13B—C14B—C15B119.71 (15)
C4A—C3A—H3AA120.3C13B—C14B—H14B120.1
C3A—C4A—C5A120.51 (17)C15B—C14B—H14B120.1
C3A—C4A—H4AA119.7C14B—C15B—C16B119.92 (15)
C5A—C4A—H4AA119.7C14B—C15B—H15B120.0
C4A—C5A—C6A119.54 (16)C16B—C15B—H15B120.0
C4A—C5A—H5AA120.2C15B—C16B—C11B120.82 (15)
C6A—C5A—H5AA120.2C15B—C16B—H16B119.6
C1A—C6A—C5A120.44 (15)C11B—C16B—H16B119.6
C1A—C6A—N1A119.82 (14)C19B—C17B—C18B104.75 (13)
C5A—C6A—N1A119.71 (14)C19B—C17B—C10B128.64 (13)
O1A—C7A—N1A122.85 (14)C18B—C17B—C10B126.48 (13)
O1A—C7A—C8A130.41 (14)N3B—C18B—C17B112.30 (13)
N1A—C7A—C8A106.74 (13)N3B—C18B—C27B120.25 (13)
C9A—C8A—C7A106.64 (13)C17B—C18B—C27B127.45 (14)
C9A—C8A—C10A128.32 (14)O2B—C19B—N4B119.10 (13)
C7A—C8A—C10A124.87 (13)O2B—C19B—C17B133.62 (14)
N2A—C9A—C8A110.07 (14)N4B—C19B—C17B107.27 (13)
N2A—C9A—C26A119.53 (13)C21B—C20B—C25B120.29 (14)
C8A—C9A—C26A130.39 (14)C21B—C20B—N4B120.75 (14)
C17A—C10A—C8A113.93 (12)C25B—C20B—N4B118.96 (14)
C17A—C10A—C11A113.52 (12)C22B—C21B—C20B119.19 (15)
C8A—C10A—C11A111.00 (13)C22B—C21B—H21B120.4
C17A—C10A—H10A105.9C20B—C21B—H21B120.4
C8A—C10A—H10A105.9C23B—C22B—C21B120.69 (16)
C11A—C10A—H10A105.9C23B—C22B—H22B119.7
C16A—C11A—C12A118.28 (14)C21B—C22B—H22B119.7
C16A—C11A—C10A120.60 (14)C24B—C23B—C22B119.87 (15)
C12A—C11A—C10A121.01 (13)C24B—C23B—H23B120.1
C13A—C12A—C11A121.06 (15)C22B—C23B—H23B120.1
C13A—C12A—H12A119.5C25B—C24B—C23B120.19 (15)
C11A—C12A—H12A119.5C25B—C24B—H24B119.9
C14A—C13A—C12A120.13 (16)C23B—C24B—H24B119.9
C14A—C13A—H13A119.9C24B—C25B—C20B119.77 (15)
C12A—C13A—H13A119.9C24B—C25B—H25B120.1
C15A—C14A—C13A119.30 (15)C20B—C25B—H25B120.1
C15A—C14A—H14A120.4C9B—C26B—H26D109.5
C13A—C14A—H14A120.4C9B—C26B—H26E109.5
C14A—C15A—C16A120.93 (16)H26D—C26B—H26E109.5
C14A—C15A—H15A119.5C9B—C26B—H26F109.5
C16A—C15A—H15A119.5H26D—C26B—H26F109.5
C15A—C16A—C11A120.29 (16)H26E—C26B—H26F109.5
C15A—C16A—H16A119.9C18B—C27B—H27D109.5
C11A—C16A—H16A119.9C18B—C27B—H27E109.5
C19A—C17A—C18A104.20 (14)H27D—C27B—H27E109.5
C19A—C17A—C10A128.55 (15)C18B—C27B—H27F109.5
C18A—C17A—C10A127.25 (14)H27D—C27B—H27F109.5
N3A—C18A—C17A112.25 (14)H27E—C27B—H27F109.5
N3A—C18A—C27A120.42 (15)C29—C28—H28A109.5
C17A—C18A—C27A127.33 (15)C29—C28—H28B109.5
O2A—C19A—N4A119.99 (14)H28A—C28—H28B109.5
O2A—C19A—C17A131.81 (15)C29—C28—H28C109.5
N4A—C19A—C17A108.11 (14)H28A—C28—H28C109.5
C9A—C26A—H26A109.5H28B—C28—H28C109.5
C9A—C26A—H26B109.5O3—C29—C28113.16 (18)
H26A—C26A—H26B109.5O3—C29—H29A108.9
C9A—C26A—H26C109.5C28—C29—H29A108.9
H26A—C26A—H26C109.5O3—C29—H29B108.9
H26B—C26A—H26C109.5C28—C29—H29B108.9
C18A—C27A—H27A109.5H29A—C29—H29B107.8
C18A—C27A—H27B109.5C29—O3—H3109.5
C7A—N1A—N2A—C9A−4.81 (17)C20A—N4A—C19A—O2A12.2 (5)
C6A—N1A—N2A—C9A−178.43 (14)C20C—N4A—C19A—O2A9.1 (5)
C18A—N3A—N4A—C19A−1.23 (16)N3A—N4A—C19A—C17A1.69 (17)
C18A—N3A—N4A—C20A172.3 (4)C20A—N4A—C19A—C17A−170.8 (5)
C18A—N3A—N4A—C20C174.5 (4)C20C—N4A—C19A—C17A−173.8 (5)
C19A—N4A—C20A—C25A−164.5 (5)C18A—C17A—C19A—O2A175.16 (16)
N3A—N4A—C20A—C25A23.5 (9)C10A—C17A—C19A—O2A−4.7 (3)
C20C—N4A—C20A—C25A−133 (9)C18A—C17A—C19A—N4A−1.39 (16)
C19A—N4A—C20A—C21A26.8 (9)C10A—C17A—C19A—N4A178.70 (14)
N3A—N4A—C20A—C21A−145.2 (5)C19B—N4B—N3B—C18B−0.79 (17)
C20C—N4A—C20A—C21A58 (9)C20B—N4B—N3B—C18B−167.49 (14)
C25A—C20A—C21A—C22A10.8 (9)C9B—N2B—N1B—C7B−2.77 (17)
N4A—C20A—C21A—C22A−179.4 (5)C9B—N2B—N1B—C6B−172.31 (13)
C20A—C21A—C22A—C23A−3.9 (7)C6B—C1B—C2B—C3B−0.9 (3)
C21A—C22A—C23A—C24A−3.9 (7)C1B—C2B—C3B—C4B0.1 (3)
C22A—C23A—C24A—C25A4.5 (8)C2B—C3B—C4B—C5B0.4 (3)
N4A—C20A—C25A—C24A−179.5 (6)C3B—C4B—C5B—C6B−0.2 (3)
C21A—C20A—C25A—C24A−10.5 (10)C2B—C1B—C6B—C5B1.2 (3)
C23A—C24A—C25A—C20A3.1 (9)C2B—C1B—C6B—N1B−178.64 (16)
C19A—N4A—C20C—C21C11.4 (10)C4B—C5B—C6B—C1B−0.6 (3)
N3A—N4A—C20C—C21C−163.6 (6)C4B—C5B—C6B—N1B179.18 (16)
C20A—N4A—C20C—C21C−139 (9)C7B—N1B—C6B—C1B29.4 (2)
C19A—N4A—C20C—C25C−157.5 (4)N2B—N1B—C6B—C1B−163.45 (15)
N3A—N4A—C20C—C25C27.5 (8)C7B—N1B—C6B—C5B−150.41 (16)
C20A—N4A—C20C—C25C52 (9)N2B—N1B—C6B—C5B16.7 (2)
C25C—C20C—C21C—C22C−13.2 (11)N2B—N1B—C7B—O1B−178.76 (14)
N4A—C20C—C21C—C22C178.4 (6)C6B—N1B—C7B—O1B−10.4 (2)
C20C—C21C—C22C—C23C2.4 (9)N2B—N1B—C7B—C8B0.17 (16)
C21C—C22C—C23C—C24C6.4 (8)C6B—N1B—C7B—C8B168.50 (14)
C22C—C23C—C24C—C25C−4.4 (8)O1B—C7B—C8B—C9B−178.72 (15)
C23C—C24C—C25C—C20C−5.9 (8)N1B—C7B—C8B—C9B2.43 (16)
C21C—C20C—C25C—C24C14.9 (11)O1B—C7B—C8B—C10B4.9 (2)
N4A—C20C—C25C—C24C−175.8 (5)N1B—C7B—C8B—C10B−173.96 (13)
C6A—C1A—C2A—C3A0.3 (3)N1B—N2B—C9B—C8B4.39 (17)
C1A—C2A—C3A—C4A−0.1 (3)N1B—N2B—C9B—C26B−174.06 (13)
C2A—C3A—C4A—C5A−0.4 (3)C7B—C8B—C9B—N2B−4.22 (17)
C3A—C4A—C5A—C6A0.7 (3)C10B—C8B—C9B—N2B171.99 (14)
C2A—C1A—C6A—C5A0.0 (2)C7B—C8B—C9B—C26B173.99 (16)
C2A—C1A—C6A—N1A178.35 (14)C10B—C8B—C9B—C26B−9.8 (3)
C4A—C5A—C6A—C1A−0.6 (2)C9B—C8B—C10B—C17B109.83 (17)
C4A—C5A—C6A—N1A−178.87 (15)C7B—C8B—C10B—C17B−74.59 (18)
C7A—N1A—C6A—C1A−47.2 (2)C9B—C8B—C10B—C11B−119.33 (17)
N2A—N1A—C6A—C1A125.08 (16)C7B—C8B—C10B—C11B56.26 (18)
C7A—N1A—C6A—C5A131.11 (17)C8B—C10B—C11B—C12B−168.74 (13)
N2A—N1A—C6A—C5A−56.6 (2)C17B—C10B—C11B—C12B−38.62 (19)
N2A—N1A—C7A—O1A−176.91 (14)C8B—C10B—C11B—C16B15.51 (19)
C6A—N1A—C7A—O1A−3.8 (3)C17B—C10B—C11B—C16B145.62 (14)
N2A—N1A—C7A—C8A3.49 (17)C16B—C11B—C12B—C13B0.2 (2)
C6A—N1A—C7A—C8A176.56 (14)C10B—C11B—C12B—C13B−175.73 (14)
O1A—C7A—C8A—C9A179.56 (16)C11B—C12B—C13B—C14B−0.8 (3)
N1A—C7A—C8A—C9A−0.87 (17)C12B—C13B—C14B—C15B0.6 (3)
O1A—C7A—C8A—C10A−4.8 (3)C13B—C14B—C15B—C16B0.2 (2)
N1A—C7A—C8A—C10A174.72 (14)C14B—C15B—C16B—C11B−0.8 (2)
N1A—N2A—C9A—C8A4.26 (17)C12B—C11B—C16B—C15B0.6 (2)
N1A—N2A—C9A—C26A−176.17 (14)C10B—C11B—C16B—C15B176.46 (14)
C7A—C8A—C9A—N2A−2.12 (17)C8B—C10B—C17B—C19B59.2 (2)
C10A—C8A—C9A—N2A−177.52 (14)C11B—C10B—C17B—C19B−70.9 (2)
C7A—C8A—C9A—C26A178.36 (17)C8B—C10B—C17B—C18B−115.95 (17)
C10A—C8A—C9A—C26A3.0 (3)C11B—C10B—C17B—C18B113.92 (17)
C9A—C8A—C10A—C17A−115.97 (17)N4B—N3B—C18B—C17B0.58 (18)
C7A—C8A—C10A—C17A69.41 (19)N4B—N3B—C18B—C27B−179.46 (14)
C9A—C8A—C10A—C11A114.39 (17)C19B—C17B—C18B—N3B−0.16 (19)
C7A—C8A—C10A—C11A−60.23 (19)C10B—C17B—C18B—N3B175.94 (15)
C17A—C10A—C11A—C16A29.1 (2)C19B—C17B—C18B—C27B179.87 (16)
C8A—C10A—C11A—C16A158.99 (14)C10B—C17B—C18B—C27B−4.0 (3)
C17A—C10A—C11A—C12A−154.73 (15)N3B—N4B—C19B—O2B−179.02 (13)
C8A—C10A—C11A—C12A−24.9 (2)C20B—N4B—C19B—O2B−13.6 (2)
C16A—C11A—C12A—C13A−0.7 (2)N3B—N4B—C19B—C17B0.71 (18)
C10A—C11A—C12A—C13A−176.92 (15)C20B—N4B—C19B—C17B166.11 (15)
C11A—C12A—C13A—C14A0.7 (3)C18B—C17B—C19B—O2B179.34 (17)
C12A—C13A—C14A—C15A0.1 (3)C10B—C17B—C19B—O2B3.4 (3)
C13A—C14A—C15A—C16A−0.9 (3)C18B—C17B—C19B—N4B−0.33 (17)
C14A—C15A—C16A—C11A0.9 (3)C10B—C17B—C19B—N4B−176.32 (15)
C12A—C11A—C16A—C15A−0.1 (2)C19B—N4B—C20B—C21B48.7 (2)
C10A—C11A—C16A—C15A176.12 (16)N3B—N4B—C20B—C21B−147.13 (15)
C8A—C10A—C17A—C19A−69.5 (2)C19B—N4B—C20B—C25B−130.94 (17)
C11A—C10A—C17A—C19A58.8 (2)N3B—N4B—C20B—C25B33.3 (2)
C8A—C10A—C17A—C18A110.58 (17)C25B—C20B—C21B—C22B0.6 (2)
C11A—C10A—C17A—C18A−121.05 (16)N4B—C20B—C21B—C22B−178.97 (15)
N4A—N3A—C18A—C17A0.32 (17)C20B—C21B—C22B—C23B−0.1 (3)
N4A—N3A—C18A—C27A−179.89 (14)C21B—C22B—C23B—C24B−0.3 (3)
C19A—C17A—C18A—N3A0.66 (17)C22B—C23B—C24B—C25B0.2 (3)
C10A—C17A—C18A—N3A−179.42 (14)C23B—C24B—C25B—C20B0.3 (3)
C19A—C17A—C18A—C27A−179.11 (16)C21B—C20B—C25B—C24B−0.7 (2)
C10A—C17A—C18A—C27A0.8 (3)N4B—C20B—C25B—C24B178.90 (15)
N3A—N4A—C19A—O2A−175.35 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O1A0.821.762.5755 (16)173
O3—H3···N3Ai0.822.112.923 (2)173
O2B—H2OB···O1B0.821.682.4970 (16)176
N2A—H2NA···N3Bii0.93 (3)1.88 (3)2.810 (2)176 (2)
N2B—H2NB···O1Aiii0.95 (2)1.75 (2)2.6922 (19)173 (2)
C1B—H1BA···O1B0.932.372.925 (2)118
C2B—H2BA···O3iv0.932.483.313 (2)149
C21A—H21A···O2A0.932.412.910 (5)114
C5B—H5BA···Cg1i0.932.893.595 (3)134
C29—H29B···Cg2iv0.972.803.492 (2)129

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2553).

References

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