4-Allyl-2-[1-(5-allyl-2-hydr­oxy-3-meth­oxy­benz­yl)-1H-benzimidazol-2-yl]-6-methoxy­phenol pyridine solvate

The title compound, C₂₈H₂₈N₂O₄·C₅H₅N, crystallizes with two mol­ecules in the asymmetric unit. In both mol­ecules, the benzimidazole ring system is essentially planar and forms dihedral angles of 85.35 (5) and 50.51 (5)° with the two benzene rings in one mol­ecule, and 82.93 (5) and 51.30 (5)° in the other mol­ecule. The hydr­oxy groups are coplanar with the attached benzene rings, whereas the meth­oxy groups are slightly twisted away from the planes of the attached benzene rings. O—H...O intra­molecular hydrogen bonds involving the hydr­oxy and meth­oxy groups generate S(6) ring motifs. In the crystal structure, mol­ecules are linked into chains along the [110] direction by O—H...N and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.143
• Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The synthesis of benzimidazoles has received much attention owing to their various biological activities such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), anti-HIV (Barreca et al., 2003), and anticancer (Demirayak et al., 2002). Recently, we reported the crystal structures of 2-(benzimidazol-2-yl)-6-methoxyphenol (Eltayeb et al., 2007a) and 2-(2-methoxynaphthalen-1-yl)-1-[(2-methoxynaphthalen-1-yl)methyl]-1H- benzimidazole (Eltayeb et al., 2007b). The title compound was synthesized as an extension of our investigations of benzimidazole derivatives. We report here the crystal structure of the title compound.

The title compound crystalizes with two molecules of the benzimidazole derivative [A and B] and two molecules of pyridine in the asymmetric unit. In both A and B, the benzimidazole ring system is essentially planar. The benzimidazole ring system makes dihedral angles of 85.35 (5)° and 50.51 (5)°, respectively, with the C1–C6 and C15—C20 benzene rings in molecule A, and 82.93 (5)° and 51.30 (5)°, respectively, in molecule B. The hydroxyl groups are coplanar with the attached benzene rings, whereas the methoxy groups are slightly twisted away from the mean plane of the attached benzene rings, as indicated by the C25–O2–C2–C3 [4.29 (18)° in molecule A and 2.11 (18)° in molecule B] and C24–O4–C17–C18 [6.52 (19)° in molecule A and 12.40 (19) ° in molecule B] torsion angles. The orientation of the allyl groups with respect to the attached benzene rings can be described by the torsion angle C3–C4–C26–C27 of 104.09 (15)° in molecule A [-81.78 (16)° in molecule B] and C18–C19–C21–C22 torsion angle of 168.38 (12)° in molecule A [171.79 (12)° in molecule B]. Bond lengths and angles in both molecules are in normal ranges (Allen et al., 1987) and are comparable to those in related structures (Eltayeb et al., 2007a; 2007b).

There are two O—H···O intramolecular hydrogen bonds involving the two hydroxyl and the two methoxyl groups [O1A—H1OA···O2A and O3A—H3OA···O4A in molecule A, and O1B—H1OB···O2B and O3B—H3OB···O4B in molecule B] (Table 1) which generate S(6) ring motifs. In addition, C—H···O intramolecular hydrogen bonds are also observed.

The crystal structure is stabilized by intermolecular O—H···N and C—H···O hydrogen bonds, which link the molecules into chains along the [1 1 0] direction (Fig. 2). The structure is further stabilized by intermolecular C—H···π interactions (Table 1), involving the N1A/C13A/C8A/N2A/C14A (centroid Cg1), C8A–C13A (centroid Cg2) and N3B/C29B—C33B (centroid Cg3) rings.

Related literature

For biological activities of benzimidazoles, see: Barreca et al. (2003); Demirayak et al. (2002); Minoura et al. (2004); Pawar et al. (2004); Tomei et al. (2003). For related structures, see: Eltayeb et al. (2007a,b). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

S2. Experimental

The title compound was synthesized by adding 5-allyl-2-hydroxy-3-methoxybenzaldehyde (0.216 g, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 0.5 h. Then zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at room temperature for 2 h. The orange precipitate obtained was washed with about 5 ml e thanol, dried, and then washed with copious amounts of diethyl ether. Pale-yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of the pyridine solution at room temperature after four weeks.

S3. Refinement

Hydroxyl H atoms were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with and C—H distances in the range 0.93–0.97 Å. The U_iso values were constrained to be 1.5U_eq of the carrier atom for methyl H atoms and 1.2U_eq for the remaining H atoms. A rotating group model was used for the methyl groups.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures

	Fig. 1. The asymmetric unit of the title compound, showing 80% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Part of the crystal packing of the title compound, viewed approximately along the c axis. Hydrogen bonds are shown as dashed lines.

4-Allyl-2-[1-(5-allyl-2-hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]- 6-methoxyphenol pyridine solvate

Crystal data

C28H28N2O4·C5H5N	Z = 4
Mr = 535.62	F(000) = 1136
Triclinic, P1	Dx = 1.288 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5355 (1) Å	Cell parameters from 16031 reflections
b = 17.3405 (3) Å	θ = 1.2–30.0°
c = 17.8604 (3) Å	µ = 0.09 mm^−1
α = 92.840 (1)°	T = 100 K
β = 105.372 (1)°	Block, pale yellow
γ = 102.523 (1)°	0.40 × 0.27 × 0.23 mm
V = 2761.80 (8) Å^3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	16031 independent reflections
Radiation source: fine-focus sealed tube	11052 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.2°
ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→24
Tmin = 0.967, Tmax = 0.980	l = −25→25
44895 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 0.0718P] where P = (Fo^2 + 2Fc^2)/3
16031 reflections	(Δ/σ)max = 0.001
741 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. The low-temparture 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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.69329 (11)	0.40199 (6)	0.28400 (6)	0.0198 (2)
H1OA	0.746 (2)	0.4550 (12)	0.2942 (11)	0.059 (6)*
O2A	0.61443 (10)	0.51795 (5)	0.35805 (5)	0.0193 (2)
O3A	0.42381 (10)	0.13523 (6)	0.09510 (5)	0.0183 (2)
H3OA	0.423 (2)	0.1324 (11)	0.0430 (11)	0.049 (6)*
O4A	0.19547 (11)	0.14126 (6)	−0.02821 (5)	0.0218 (2)
N1A	0.37505 (12)	0.04523 (6)	0.28948 (6)	0.0144 (2)
N2A	0.50051 (12)	0.16685 (6)	0.27712 (6)	0.0133 (2)
C1A	0.56764 (14)	0.38543 (7)	0.30790 (7)	0.0142 (3)
C2A	0.52048 (14)	0.44352 (7)	0.34607 (7)	0.0154 (3)
C3A	0.38987 (15)	0.42383 (8)	0.36832 (7)	0.0170 (3)
H3A	0.3594	0.4628	0.3934	0.020*
C4A	0.30335 (15)	0.34527 (8)	0.35323 (8)	0.0175 (3)
C5A	0.35165 (15)	0.28816 (8)	0.31613 (7)	0.0167 (3)
H5A	0.2948	0.2360	0.3060	0.020*
C6A	0.48255 (14)	0.30686 (7)	0.29373 (7)	0.0134 (2)
C7A	0.53506 (15)	0.24556 (7)	0.25165 (7)	0.0147 (3)
H7A	0.4881	0.2421	0.1959	0.018*
H7B	0.6425	0.2630	0.2605	0.018*
C8A	0.58195 (14)	0.14521 (7)	0.34609 (7)	0.0138 (3)
C9A	0.71464 (15)	0.18474 (8)	0.40171 (8)	0.0183 (3)
H9A	0.7651	0.2359	0.3974	0.022*
C10A	0.76712 (15)	0.14376 (8)	0.46368 (8)	0.0203 (3)
H10A	0.8553	0.1680	0.5020	0.024*
C11A	0.69072 (15)	0.06663 (8)	0.47024 (8)	0.0205 (3)
H11A	0.7298	0.0408	0.5125	0.025*
C12A	0.55826 (15)	0.02824 (8)	0.41505 (7)	0.0179 (3)
H12A	0.5078	−0.0228	0.4195	0.021*
C13A	0.50319 (14)	0.06894 (7)	0.35252 (7)	0.0148 (3)
C14A	0.37763 (14)	0.10462 (7)	0.24591 (7)	0.0132 (2)
C15A	0.25636 (14)	0.10407 (7)	0.17408 (7)	0.0142 (3)
C16A	0.28195 (14)	0.12015 (7)	0.10242 (7)	0.0151 (3)
C17A	0.15828 (15)	0.12027 (8)	0.03814 (7)	0.0169 (3)
C18A	0.01458 (15)	0.09840 (8)	0.04422 (8)	0.0183 (3)
H18A	−0.0658	0.0972	0.0008	0.022*
C19A	−0.01247 (14)	0.07781 (8)	0.11501 (8)	0.0168 (3)
C20A	0.10845 (14)	0.08213 (7)	0.17913 (7)	0.0159 (3)
H20A	0.0919	0.0703	0.2267	0.019*
C21A	−0.17410 (15)	0.05094 (8)	0.11641 (8)	0.0200 (3)
H21A	−0.2180	0.0966	0.1110	0.024*
H21B	−0.2277	0.0127	0.0709	0.024*
C22A	−0.20089 (15)	0.01432 (8)	0.18715 (8)	0.0201 (3)
H22A	−0.1487	−0.0234	0.2061	0.024*
C23A	−0.29377 (16)	0.03243 (9)	0.22407 (8)	0.0247 (3)
H23A	−0.3475	0.0700	0.2065	0.030*
H23B	−0.3058	0.0077	0.2677	0.030*
C24A	0.07727 (17)	0.14857 (9)	−0.09374 (8)	0.0255 (3)
H24A	0.1181	0.1666	−0.1352	0.038*
H24B	0.0264	0.1862	−0.0788	0.038*
H24C	0.0078	0.0978	−0.1112	0.038*
C25A	0.58045 (18)	0.57919 (8)	0.40139 (8)	0.0248 (3)
H25A	0.6582	0.6269	0.4093	0.037*
H25B	0.5735	0.5628	0.4511	0.037*
H25C	0.4867	0.5891	0.3729	0.037*
C26A	0.15495 (15)	0.32332 (9)	0.37223 (8)	0.0220 (3)
H26A	0.1489	0.2751	0.3977	0.026*
H26B	0.1484	0.3655	0.4080	0.026*
C27A	0.02750 (16)	0.31078 (9)	0.29955 (9)	0.0264 (3)
H27A	0.0083	0.3554	0.2758	0.032*
C28A	−0.05956 (17)	0.24102 (9)	0.26674 (9)	0.0303 (4)
H28A	−0.0436	0.1951	0.2889	0.036*
H28B	−0.1371	0.2376	0.2214	0.036*
O1B	1.19577 (11)	0.90182 (6)	0.29353 (6)	0.0203 (2)
H1OB	1.235 (2)	0.9548 (13)	0.2989 (12)	0.068 (7)*
O2B	1.09294 (10)	1.01306 (5)	0.36193 (5)	0.0193 (2)
O3B	0.96691 (10)	0.64026 (6)	0.10956 (5)	0.0199 (2)
H3OB	0.986 (2)	0.6472 (12)	0.0579 (12)	0.070 (7)*
O4B	0.75469 (11)	0.64354 (6)	−0.02223 (5)	0.0232 (2)
N1B	0.88956 (12)	0.54180 (6)	0.29220 (6)	0.0146 (2)
N2B	1.02152 (12)	0.66375 (6)	0.28601 (6)	0.0142 (2)
C1B	1.06728 (14)	0.88114 (7)	0.31508 (7)	0.0147 (3)
C2B	1.00811 (15)	0.93630 (7)	0.34968 (7)	0.0156 (3)
C3B	0.87434 (15)	0.91182 (8)	0.36796 (7)	0.0168 (3)
H3B	0.8367	0.9487	0.3913	0.020*
C4B	0.79479 (14)	0.83190 (8)	0.35160 (7)	0.0162 (3)
C5B	0.85647 (15)	0.77762 (8)	0.31965 (7)	0.0163 (3)
H5B	0.8064	0.7242	0.3101	0.020*
C6B	0.99201 (14)	0.80129 (7)	0.30143 (7)	0.0147 (3)
C7B	1.05948 (15)	0.74390 (7)	0.26440 (8)	0.0166 (3)
H7C	1.0246	0.7422	0.2080	0.020*
H7D	1.1676	0.7633	0.2801	0.020*
C8B	1.09676 (14)	0.63925 (8)	0.35443 (7)	0.0148 (3)
C9B	1.22821 (15)	0.67600 (8)	0.41216 (8)	0.0195 (3)
H9B	1.2819	0.7270	0.4099	0.023*
C10B	1.27469 (16)	0.63259 (9)	0.47308 (8)	0.0227 (3)
H10B	1.3622	0.6548	0.5126	0.027*
C11B	1.19300 (16)	0.55598 (9)	0.47661 (8)	0.0216 (3)
H11B	1.2273	0.5286	0.5185	0.026*
C12B	1.06213 (15)	0.51991 (8)	0.41906 (7)	0.0185 (3)
H12B	1.0086	0.4689	0.4216	0.022*
C13B	1.01378 (14)	0.56272 (7)	0.35738 (7)	0.0147 (3)
C14B	0.89811 (14)	0.60316 (7)	0.25106 (7)	0.0136 (3)
C15B	0.78385 (14)	0.60625 (7)	0.17782 (7)	0.0147 (3)
C16B	0.82149 (14)	0.62438 (7)	0.10954 (7)	0.0154 (3)
C17B	0.70587 (15)	0.62437 (8)	0.04144 (7)	0.0177 (3)
C18B	0.55764 (15)	0.60432 (8)	0.04185 (8)	0.0190 (3)
H18B	0.4825	0.6038	−0.0038	0.023*
C19B	0.51918 (15)	0.58466 (8)	0.11046 (8)	0.0179 (3)
C20B	0.63284 (14)	0.58603 (7)	0.17762 (7)	0.0160 (3)
H15B	0.6090	0.5733	0.2234	0.019*
C21B	0.35492 (15)	0.56373 (9)	0.10803 (8)	0.0225 (3)
H21C	0.3162	0.6108	0.0992	0.027*
H21D	0.3009	0.5241	0.0637	0.027*
C22B	0.32253 (15)	0.53259 (9)	0.17998 (8)	0.0237 (3)
H22B	0.3570	0.4883	0.1966	0.028*
C23B	0.24884 (18)	0.56352 (11)	0.22121 (9)	0.0354 (4)
H23C	0.2128	0.6078	0.2063	0.042*
H23D	0.2326	0.5412	0.2654	0.042*
C24B	0.64838 (17)	0.65859 (9)	−0.08925 (8)	0.0263 (3)
H24D	0.6974	0.6746	−0.1284	0.039*
H24E	0.6054	0.7002	−0.0748	0.039*
H24F	0.5707	0.6111	−0.1097	0.039*
C25B	1.03920 (16)	1.07091 (8)	0.39887 (8)	0.0224 (3)
H25D	1.1056	1.1223	0.4037	0.034*
H25E	1.0352	1.0573	0.4498	0.034*
H25F	0.9408	1.0720	0.3679	0.034*
C26B	0.64624 (15)	0.80558 (8)	0.36944 (8)	0.0193 (3)
H26C	0.5897	0.8457	0.3563	0.023*
H26D	0.5897	0.7567	0.3364	0.023*
C27B	0.66083 (15)	0.79207 (8)	0.45316 (8)	0.0202 (3)
H27B	0.7281	0.7625	0.4759	0.024*
C28B	0.58663 (17)	0.81850 (9)	0.49721 (9)	0.0271 (3)
H28C	0.5183	0.8483	0.4768	0.033*
H28D	0.6025	0.8073	0.5488	0.033*
N3A	0.92807 (13)	0.34672 (7)	0.01349 (7)	0.0224 (3)
C29A	0.96230 (16)	0.41376 (9)	0.06201 (8)	0.0238 (3)
H29A	1.0380	0.4557	0.0576	0.029*
C30A	0.89068 (16)	0.42350 (9)	0.11814 (8)	0.0248 (3)
H30A	0.9178	0.4709	0.1509	0.030*
C31A	0.77808 (16)	0.36174 (9)	0.12486 (8)	0.0255 (3)
H31A	0.7272	0.3668	0.1619	0.031*
C32A	0.74217 (16)	0.29227 (9)	0.07563 (8)	0.0251 (3)
H32A	0.6672	0.2495	0.0792	0.030*
C33A	0.81932 (16)	0.28732 (9)	0.02099 (8)	0.0233 (3)
H33A	0.7943	0.2403	−0.0122	0.028*
N3B	0.49267 (13)	0.13148 (7)	0.95301 (6)	0.0205 (3)
C29B	0.57110 (15)	0.08262 (8)	0.93302 (8)	0.0215 (3)
H29B	0.5889	0.0420	0.9636	0.026*
C30B	0.62726 (16)	0.08964 (9)	0.86879 (8)	0.0239 (3)
H30B	0.6816	0.0546	0.8570	0.029*
C31B	0.60102 (16)	0.14943 (9)	0.82286 (8)	0.0260 (3)
H31B	0.6380	0.1557	0.7797	0.031*
C32B	0.51883 (17)	0.19984 (9)	0.84209 (8)	0.0259 (3)
H32B	0.4986	0.2404	0.8119	0.031*
C33B	0.46716 (16)	0.18877 (8)	0.90711 (8)	0.0222 (3)
H33B	0.4118	0.2229	0.9197	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0206 (5)	0.0133 (5)	0.0267 (5)	−0.0003 (4)	0.0126 (4)	−0.0001 (4)
O2A	0.0236 (5)	0.0117 (5)	0.0224 (5)	0.0019 (4)	0.0085 (4)	−0.0017 (4)
O3A	0.0159 (5)	0.0238 (5)	0.0162 (5)	0.0035 (4)	0.0072 (4)	0.0022 (4)
O4A	0.0209 (5)	0.0316 (6)	0.0138 (4)	0.0071 (4)	0.0052 (4)	0.0070 (4)
N1A	0.0151 (6)	0.0130 (5)	0.0151 (5)	0.0028 (4)	0.0048 (4)	0.0020 (4)
N2A	0.0133 (5)	0.0114 (5)	0.0148 (5)	0.0017 (4)	0.0042 (4)	0.0012 (4)
C1A	0.0152 (6)	0.0146 (6)	0.0133 (6)	0.0041 (5)	0.0039 (5)	0.0034 (5)
C2A	0.0184 (7)	0.0122 (6)	0.0138 (6)	0.0027 (5)	0.0027 (5)	0.0009 (5)
C3A	0.0213 (7)	0.0157 (7)	0.0158 (6)	0.0079 (5)	0.0056 (5)	0.0009 (5)
C4A	0.0175 (7)	0.0186 (7)	0.0177 (6)	0.0057 (5)	0.0061 (5)	0.0026 (5)
C5A	0.0171 (7)	0.0137 (6)	0.0189 (6)	0.0027 (5)	0.0051 (5)	0.0029 (5)
C6A	0.0145 (6)	0.0138 (6)	0.0117 (6)	0.0041 (5)	0.0027 (5)	0.0015 (5)
C7A	0.0175 (7)	0.0108 (6)	0.0169 (6)	0.0024 (5)	0.0072 (5)	0.0027 (5)
C8A	0.0141 (6)	0.0158 (6)	0.0132 (6)	0.0046 (5)	0.0059 (5)	0.0026 (5)
C9A	0.0166 (7)	0.0177 (7)	0.0194 (6)	0.0019 (5)	0.0059 (5)	−0.0019 (5)
C10A	0.0148 (7)	0.0279 (8)	0.0165 (6)	0.0060 (5)	0.0015 (5)	−0.0015 (6)
C11A	0.0223 (7)	0.0267 (8)	0.0159 (6)	0.0121 (6)	0.0054 (6)	0.0058 (6)
C12A	0.0206 (7)	0.0188 (7)	0.0171 (6)	0.0070 (5)	0.0077 (6)	0.0054 (5)
C13A	0.0156 (7)	0.0153 (6)	0.0149 (6)	0.0043 (5)	0.0066 (5)	−0.0005 (5)
C14A	0.0133 (6)	0.0121 (6)	0.0150 (6)	0.0026 (5)	0.0060 (5)	0.0000 (5)
C15A	0.0148 (6)	0.0124 (6)	0.0146 (6)	0.0032 (5)	0.0030 (5)	0.0019 (5)
C16A	0.0152 (7)	0.0140 (6)	0.0164 (6)	0.0032 (5)	0.0052 (5)	0.0020 (5)
C17A	0.0202 (7)	0.0174 (7)	0.0138 (6)	0.0058 (5)	0.0049 (5)	0.0029 (5)
C18A	0.0167 (7)	0.0223 (7)	0.0151 (6)	0.0054 (5)	0.0026 (5)	0.0030 (5)
C19A	0.0148 (7)	0.0179 (7)	0.0175 (6)	0.0050 (5)	0.0034 (5)	0.0020 (5)
C20A	0.0177 (7)	0.0156 (6)	0.0147 (6)	0.0042 (5)	0.0052 (5)	0.0021 (5)
C21A	0.0144 (7)	0.0253 (8)	0.0192 (7)	0.0044 (5)	0.0035 (5)	0.0012 (6)
C22A	0.0148 (7)	0.0231 (7)	0.0199 (7)	0.0025 (5)	0.0024 (5)	0.0013 (6)
C23A	0.0203 (8)	0.0319 (8)	0.0213 (7)	0.0042 (6)	0.0065 (6)	0.0016 (6)
C24A	0.0269 (8)	0.0359 (9)	0.0157 (6)	0.0121 (6)	0.0047 (6)	0.0086 (6)
C25A	0.0363 (9)	0.0145 (7)	0.0240 (7)	0.0068 (6)	0.0093 (7)	−0.0020 (6)
C26A	0.0210 (7)	0.0219 (7)	0.0273 (7)	0.0063 (5)	0.0127 (6)	0.0030 (6)
C27A	0.0203 (8)	0.0278 (8)	0.0370 (8)	0.0111 (6)	0.0120 (7)	0.0142 (7)
C28A	0.0236 (8)	0.0332 (9)	0.0347 (9)	0.0090 (6)	0.0065 (7)	0.0088 (7)
O1B	0.0199 (5)	0.0129 (5)	0.0303 (5)	0.0007 (4)	0.0132 (4)	0.0021 (4)
O2B	0.0225 (5)	0.0115 (5)	0.0241 (5)	0.0028 (4)	0.0084 (4)	−0.0013 (4)
O3B	0.0178 (5)	0.0268 (5)	0.0167 (5)	0.0053 (4)	0.0074 (4)	0.0031 (4)
O4B	0.0240 (6)	0.0339 (6)	0.0149 (5)	0.0106 (4)	0.0067 (4)	0.0084 (4)
N1B	0.0154 (6)	0.0145 (5)	0.0134 (5)	0.0028 (4)	0.0038 (4)	0.0012 (4)
N2B	0.0153 (6)	0.0113 (5)	0.0154 (5)	0.0024 (4)	0.0044 (4)	0.0008 (4)
C1B	0.0153 (6)	0.0148 (6)	0.0141 (6)	0.0033 (5)	0.0044 (5)	0.0018 (5)
C2B	0.0185 (7)	0.0128 (6)	0.0139 (6)	0.0029 (5)	0.0027 (5)	0.0013 (5)
C3B	0.0204 (7)	0.0173 (7)	0.0141 (6)	0.0072 (5)	0.0051 (5)	0.0010 (5)
C4B	0.0156 (7)	0.0187 (7)	0.0144 (6)	0.0041 (5)	0.0041 (5)	0.0024 (5)
C5B	0.0180 (7)	0.0127 (6)	0.0171 (6)	0.0008 (5)	0.0054 (5)	0.0018 (5)
C6B	0.0164 (7)	0.0138 (6)	0.0137 (6)	0.0034 (5)	0.0043 (5)	0.0011 (5)
C7B	0.0190 (7)	0.0119 (6)	0.0202 (6)	0.0025 (5)	0.0084 (5)	0.0035 (5)
C8B	0.0156 (7)	0.0156 (6)	0.0143 (6)	0.0036 (5)	0.0062 (5)	0.0006 (5)
C9B	0.0178 (7)	0.0191 (7)	0.0195 (7)	0.0014 (5)	0.0049 (6)	−0.0020 (5)
C10B	0.0183 (7)	0.0289 (8)	0.0173 (7)	0.0046 (6)	0.0007 (6)	−0.0031 (6)
C11B	0.0233 (8)	0.0279 (8)	0.0160 (6)	0.0117 (6)	0.0044 (6)	0.0054 (6)
C12B	0.0216 (7)	0.0190 (7)	0.0171 (6)	0.0065 (5)	0.0073 (6)	0.0055 (5)
C13B	0.0148 (6)	0.0154 (6)	0.0147 (6)	0.0040 (5)	0.0056 (5)	0.0000 (5)
C14B	0.0143 (6)	0.0119 (6)	0.0152 (6)	0.0028 (5)	0.0059 (5)	0.0002 (5)
C15B	0.0160 (7)	0.0118 (6)	0.0156 (6)	0.0035 (5)	0.0034 (5)	0.0004 (5)
C16B	0.0160 (7)	0.0147 (6)	0.0166 (6)	0.0047 (5)	0.0056 (5)	0.0019 (5)
C17B	0.0224 (7)	0.0184 (7)	0.0139 (6)	0.0073 (5)	0.0053 (5)	0.0035 (5)
C18B	0.0181 (7)	0.0211 (7)	0.0169 (6)	0.0070 (5)	0.0017 (5)	0.0025 (5)
C19B	0.0175 (7)	0.0171 (7)	0.0185 (6)	0.0052 (5)	0.0034 (5)	0.0013 (5)
C20B	0.0177 (7)	0.0149 (6)	0.0163 (6)	0.0038 (5)	0.0061 (5)	0.0026 (5)
C21B	0.0160 (7)	0.0277 (8)	0.0218 (7)	0.0054 (5)	0.0021 (6)	0.0017 (6)
C22B	0.0156 (7)	0.0303 (8)	0.0238 (7)	0.0049 (6)	0.0039 (6)	0.0017 (6)
C23B	0.0277 (9)	0.0536 (11)	0.0290 (8)	0.0180 (8)	0.0086 (7)	0.0032 (8)
C24B	0.0300 (9)	0.0364 (9)	0.0156 (7)	0.0147 (7)	0.0055 (6)	0.0087 (6)
C25B	0.0290 (8)	0.0160 (7)	0.0219 (7)	0.0073 (6)	0.0058 (6)	−0.0027 (6)
C26B	0.0158 (7)	0.0228 (7)	0.0186 (6)	0.0031 (5)	0.0051 (5)	0.0009 (5)
C27B	0.0199 (7)	0.0184 (7)	0.0218 (7)	0.0031 (5)	0.0064 (6)	0.0020 (6)
C28B	0.0276 (8)	0.0297 (8)	0.0247 (7)	0.0035 (6)	0.0111 (7)	0.0023 (6)
N3A	0.0174 (6)	0.0311 (7)	0.0174 (6)	0.0037 (5)	0.0048 (5)	0.0013 (5)
C29A	0.0217 (8)	0.0229 (8)	0.0230 (7)	−0.0008 (6)	0.0050 (6)	0.0029 (6)
C30A	0.0249 (8)	0.0237 (8)	0.0230 (7)	0.0071 (6)	0.0024 (6)	−0.0040 (6)
C31A	0.0216 (8)	0.0393 (9)	0.0178 (7)	0.0092 (6)	0.0079 (6)	0.0012 (6)
C32A	0.0197 (8)	0.0282 (8)	0.0245 (7)	−0.0016 (6)	0.0072 (6)	0.0036 (6)
C33A	0.0205 (7)	0.0248 (8)	0.0212 (7)	0.0026 (6)	0.0034 (6)	−0.0015 (6)
N3B	0.0172 (6)	0.0249 (7)	0.0176 (6)	0.0021 (5)	0.0045 (5)	0.0004 (5)
C29B	0.0168 (7)	0.0219 (7)	0.0213 (7)	0.0016 (5)	0.0006 (6)	0.0012 (6)
C30B	0.0179 (7)	0.0259 (8)	0.0254 (7)	0.0043 (6)	0.0046 (6)	−0.0074 (6)
C31B	0.0227 (8)	0.0351 (9)	0.0180 (7)	−0.0005 (6)	0.0086 (6)	−0.0017 (6)
C32B	0.0252 (8)	0.0288 (8)	0.0228 (7)	0.0048 (6)	0.0059 (6)	0.0065 (6)
C33B	0.0219 (7)	0.0228 (7)	0.0226 (7)	0.0058 (6)	0.0072 (6)	0.0009 (6)

Geometric parameters (Å, º)

O1A—C1A	1.3544 (15)	N2B—C8B	1.3811 (16)
O1A—H1OA	0.93 (2)	N2B—C7B	1.4562 (15)
O2A—C2A	1.3724 (15)	C1B—C6B	1.3909 (17)
O2A—C25A	1.4258 (16)	C1B—C2B	1.4055 (18)
O3A—C16A	1.3635 (15)	C2B—C3B	1.3833 (18)
O3A—H3OA	0.929 (19)	C3B—C4B	1.4029 (18)
O4A—C17A	1.3684 (15)	C3B—H3B	0.93
O4A—C24A	1.4260 (16)	C4B—C5B	1.3864 (18)
N1A—C14A	1.3211 (16)	C4B—C26B	1.5132 (18)
N1A—C13A	1.3917 (16)	C5B—C6B	1.3968 (17)
N2A—C14A	1.3761 (15)	C5B—H5B	0.93
N2A—C8A	1.3878 (16)	C6B—C7B	1.5099 (18)
N2A—C7A	1.4575 (15)	C7B—H7C	0.97
C1A—C6A	1.3987 (17)	C7B—H7D	0.97
C1A—C2A	1.4044 (18)	C8B—C9B	1.3942 (18)
C2A—C3A	1.3845 (18)	C8B—C13B	1.4013 (17)
C3A—C4A	1.4026 (18)	C9B—C10B	1.3846 (19)
C3A—H3A	0.93	C9B—H9B	0.93
C4A—C5A	1.3880 (18)	C10B—C11B	1.400 (2)
C4A—C26A	1.5153 (18)	C10B—H10B	0.93
C5A—C6A	1.3875 (17)	C11B—C12B	1.3866 (19)
C5A—H5A	0.93	C11B—H11B	0.93
C6A—C7A	1.5156 (17)	C12B—C13B	1.3919 (18)
C7A—H7A	0.97	C12B—H12B	0.93
C7A—H7B	0.97	C14B—C15B	1.4757 (17)
C8A—C9A	1.3956 (18)	C15B—C16B	1.3914 (17)
C8A—C13A	1.3988 (17)	C15B—C20B	1.4052 (18)
C9A—C10A	1.3854 (19)	C16B—C17B	1.4085 (18)
C9A—H9A	0.93	C17B—C18B	1.3826 (19)
C10A—C11A	1.4040 (19)	C18B—C19B	1.4062 (18)
C10A—H10A	0.93	C18B—H18B	0.93
C11A—C12A	1.3857 (19)	C19B—C20B	1.3823 (18)
C11A—H11A	0.93	C19B—C21B	1.5175 (19)
C12A—C13A	1.3961 (18)	C20B—H15B	0.93
C12A—H12A	0.93	C21B—C22B	1.4983 (19)
C14A—C15A	1.4802 (17)	C21B—H21C	0.97
C15A—C16A	1.3952 (17)	C21B—H21D	0.97
C15A—C20A	1.4072 (18)	C22B—C23B	1.312 (2)
C16A—C17A	1.4114 (18)	C22B—H22B	0.93
C17A—C18A	1.3750 (18)	C23B—H23C	0.93
C18A—C19A	1.4037 (18)	C23B—H23D	0.93
C18A—H18A	0.93	C24B—H24D	0.96
C19A—C20A	1.3785 (18)	C24B—H24E	0.96
C19A—C21A	1.5176 (18)	C24B—H24F	0.96
C20A—H20A	0.93	C25B—H25D	0.96
C21A—C22A	1.4984 (18)	C25B—H25E	0.96
C21A—H21A	0.97	C25B—H25F	0.96
C21A—H21B	0.97	C26B—C27B	1.4996 (18)
C22A—C23A	1.3143 (19)	C26B—H26C	0.97
C22A—H22A	0.93	C26B—H26D	0.97
C23A—H23A	0.93	C27B—C28B	1.3151 (19)
C23A—H23B	0.93	C27B—H27B	0.93
C24A—H24A	0.96	C28B—H28C	0.93
C24A—H24B	0.96	C28B—H28D	0.93
C24A—H24C	0.96	N3A—C33A	1.3336 (17)
C25A—H25A	0.96	N3A—C29A	1.3397 (18)
C25A—H25B	0.96	C29A—C30A	1.377 (2)
C25A—H25C	0.96	C29A—H29A	0.93
C26A—C27A	1.493 (2)	C30A—C31A	1.377 (2)
C26A—H26A	0.97	C30A—H30A	0.93
C26A—H26B	0.97	C31A—C32A	1.378 (2)
C27A—C28A	1.316 (2)	C31A—H31A	0.93
C27A—H27A	0.93	C32A—C33A	1.3786 (19)
C28A—H28A	0.93	C32A—H32A	0.93
C28A—H28B	0.93	C33A—H33A	0.93
O1B—C1B	1.3606 (15)	N3B—C29B	1.3383 (18)
O1B—H1OB	0.90 (2)	N3B—C33B	1.3408 (18)
O2B—C2B	1.3727 (15)	C29B—C30B	1.389 (2)
O2B—C25B	1.4285 (16)	C29B—H29B	0.93
O3B—C16B	1.3538 (15)	C30B—C31B	1.378 (2)
O3B—H3OB	0.99 (2)	C30B—H30B	0.93
O4B—C17B	1.3679 (15)	C31B—C32B	1.381 (2)
O4B—C24B	1.4252 (16)	C31B—H31B	0.93
N1B—C14B	1.3229 (16)	C32B—C33B	1.3830 (19)
N1B—C13B	1.3895 (16)	C32B—H32B	0.93
N2B—C14B	1.3740 (15)	C33B—H33B	0.93
C1A—O1A—H1OA	114.9 (12)	C4B—C3B—H3B	119.7
C2A—O2A—C25A	117.52 (10)	C5B—C4B—C3B	118.40 (12)
C16A—O3A—H3OA	111.5 (12)	C5B—C4B—C26B	120.93 (12)
C17A—O4A—C24A	117.37 (10)	C3B—C4B—C26B	120.67 (12)
C14A—N1A—C13A	105.60 (10)	C4B—C5B—C6B	121.56 (12)
C14A—N2A—C8A	106.81 (10)	C4B—C5B—H5B	119.2
C14A—N2A—C7A	128.94 (11)	C6B—C5B—H5B	119.2
C8A—N2A—C7A	123.80 (10)	C1B—C6B—C5B	119.63 (12)
O1A—C1A—C6A	117.93 (11)	C1B—C6B—C7B	117.63 (11)
O1A—C1A—C2A	122.79 (11)	C5B—C6B—C7B	122.70 (11)
C6A—C1A—C2A	119.28 (12)	N2B—C7B—C6B	112.87 (10)
O2A—C2A—C3A	125.45 (12)	N2B—C7B—H7C	109.0
O2A—C2A—C1A	113.95 (11)	C6B—C7B—H7C	109.0
C3A—C2A—C1A	120.60 (12)	N2B—C7B—H7D	109.0
C2A—C3A—C4A	120.20 (12)	C6B—C7B—H7D	109.0
C2A—C3A—H3A	119.9	H7C—C7B—H7D	107.8
C4A—C3A—H3A	119.9	N2B—C8B—C9B	131.90 (12)
C5A—C4A—C3A	118.76 (12)	N2B—C8B—C13B	105.64 (11)
C5A—C4A—C26A	119.99 (12)	C9B—C8B—C13B	122.45 (12)
C3A—C4A—C26A	121.15 (12)	C10B—C9B—C8B	116.54 (13)
C6A—C5A—C4A	121.75 (12)	C10B—C9B—H9B	121.7
C6A—C5A—H5A	119.1	C8B—C9B—H9B	121.7
C4A—C5A—H5A	119.1	C9B—C10B—C11B	121.57 (13)
C5A—C6A—C1A	119.40 (12)	C9B—C10B—H10B	119.2
C5A—C6A—C7A	122.38 (11)	C11B—C10B—H10B	119.2
C1A—C6A—C7A	118.18 (11)	C12B—C11B—C10B	121.54 (13)
N2A—C7A—C6A	113.00 (10)	C12B—C11B—H11B	119.2
N2A—C7A—H7A	109.0	C10B—C11B—H11B	119.2
C6A—C7A—H7A	109.0	C11B—C12B—C13B	117.64 (12)
N2A—C7A—H7B	109.0	C11B—C12B—H12B	121.2
C6A—C7A—H7B	109.0	C13B—C12B—H12B	121.2
H7A—C7A—H7B	107.8	N1B—C13B—C12B	130.21 (12)
N2A—C8A—C9A	131.98 (12)	N1B—C13B—C8B	109.53 (11)
N2A—C8A—C13A	105.56 (11)	C12B—C13B—C8B	120.25 (12)
C9A—C8A—C13A	122.46 (12)	N1B—C14B—N2B	112.18 (11)
C10A—C9A—C8A	116.43 (12)	N1B—C14B—C15B	123.12 (11)
C10A—C9A—H9A	121.8	N2B—C14B—C15B	124.66 (11)
C8A—C9A—H9A	121.8	C16B—C15B—C20B	120.20 (12)
C9A—C10A—C11A	121.77 (13)	C16B—C15B—C14B	121.96 (11)
C9A—C10A—H10A	119.1	C20B—C15B—C14B	117.76 (11)
C11A—C10A—H10A	119.1	O3B—C16B—C15B	119.68 (11)
C12A—C11A—C10A	121.31 (12)	O3B—C16B—C17B	121.62 (11)
C12A—C11A—H11A	119.3	C15B—C16B—C17B	118.70 (12)
C10A—C11A—H11A	119.3	O4B—C17B—C18B	125.26 (12)
C11A—C12A—C13A	117.66 (12)	O4B—C17B—C16B	114.11 (11)
C11A—C12A—H12A	121.2	C18B—C17B—C16B	120.61 (12)
C13A—C12A—H12A	121.2	C17B—C18B—C19B	120.78 (12)
N1A—C13A—C12A	129.94 (12)	C17B—C18B—H18B	119.6
N1A—C13A—C8A	109.70 (11)	C19B—C18B—H18B	119.6
C12A—C13A—C8A	120.35 (12)	C20B—C19B—C18B	118.57 (12)
N1A—C14A—N2A	112.31 (11)	C20B—C19B—C21B	122.68 (12)
N1A—C14A—C15A	122.58 (11)	C18B—C19B—C21B	118.75 (12)
N2A—C14A—C15A	125.03 (11)	C19B—C20B—C15B	121.11 (12)
C16A—C15A—C20A	119.61 (12)	C19B—C20B—H15B	119.4
C16A—C15A—C14A	123.35 (11)	C15B—C20B—H15B	119.4
C20A—C15A—C14A	116.96 (11)	C22B—C21B—C19B	115.21 (11)
O3A—C16A—C15A	120.33 (11)	C22B—C21B—H21C	108.5
O3A—C16A—C17A	121.05 (11)	C19B—C21B—H21C	108.5
C15A—C16A—C17A	118.62 (12)	C22B—C21B—H21D	108.5
O4A—C17A—C18A	125.04 (12)	C19B—C21B—H21D	108.5
O4A—C17A—C16A	114.28 (11)	H21C—C21B—H21D	107.5
C18A—C17A—C16A	120.65 (12)	C23B—C22B—C21B	124.46 (15)
C17A—C18A—C19A	120.90 (12)	C23B—C22B—H22B	117.8
C17A—C18A—H18A	119.6	C21B—C22B—H22B	117.8
C19A—C18A—H18A	119.6	C22B—C23B—H23C	120.0
C20A—C19A—C18A	118.54 (12)	C22B—C23B—H23D	120.0
C20A—C19A—C21A	123.52 (12)	H23C—C23B—H23D	120.0
C18A—C19A—C21A	117.93 (11)	O4B—C24B—H24D	109.5
C19A—C20A—C15A	121.43 (12)	O4B—C24B—H24E	109.5
C19A—C20A—H20A	119.3	H24D—C24B—H24E	109.5
C15A—C20A—H20A	119.3	O4B—C24B—H24F	109.5
C22A—C21A—C19A	116.96 (11)	H24D—C24B—H24F	109.5
C22A—C21A—H21A	108.1	H24E—C24B—H24F	109.5
C19A—C21A—H21A	108.1	O2B—C25B—H25D	109.5
C22A—C21A—H21B	108.1	O2B—C25B—H25E	109.5
C19A—C21A—H21B	108.1	H25D—C25B—H25E	109.5
H21A—C21A—H21B	107.3	O2B—C25B—H25F	109.5
C23A—C22A—C21A	123.88 (14)	H25D—C25B—H25F	109.5
C23A—C22A—H22A	118.1	H25E—C25B—H25F	109.5
C21A—C22A—H22A	118.1	C27B—C26B—C4B	113.79 (11)
C22A—C23A—H23A	120.0	C27B—C26B—H26C	108.8
C22A—C23A—H23B	120.0	C4B—C26B—H26C	108.8
H23A—C23A—H23B	120.0	C27B—C26B—H26D	108.8
O4A—C24A—H24A	109.5	C4B—C26B—H26D	108.8
O4A—C24A—H24B	109.5	H26C—C26B—H26D	107.7
H24A—C24A—H24B	109.5	C28B—C27B—C26B	125.58 (14)
O4A—C24A—H24C	109.5	C28B—C27B—H27B	117.2
H24A—C24A—H24C	109.5	C26B—C27B—H27B	117.2
H24B—C24A—H24C	109.5	C27B—C28B—H28C	120.0
O2A—C25A—H25A	109.5	C27B—C28B—H28D	120.0
O2A—C25A—H25B	109.5	H28C—C28B—H28D	120.0
H25A—C25A—H25B	109.5	C33A—N3A—C29A	117.41 (12)
O2A—C25A—H25C	109.5	N3A—C29A—C30A	123.10 (13)
H25A—C25A—H25C	109.5	N3A—C29A—H29A	118.4
H25B—C25A—H25C	109.5	C30A—C29A—H29A	118.4
C27A—C26A—C4A	110.61 (11)	C29A—C30A—C31A	118.78 (13)
C27A—C26A—H26A	109.5	C29A—C30A—H30A	120.6
C4A—C26A—H26A	109.5	C31A—C30A—H30A	120.6
C27A—C26A—H26B	109.5	C30A—C31A—C32A	118.77 (13)
C4A—C26A—H26B	109.5	C30A—C31A—H31A	120.6
H26A—C26A—H26B	108.1	C32A—C31A—H31A	120.6
C28A—C27A—C26A	124.60 (14)	C31A—C32A—C33A	118.84 (13)
C28A—C27A—H27A	117.7	C31A—C32A—H32A	120.6
C26A—C27A—H27A	117.7	C33A—C32A—H32A	120.6
C27A—C28A—H28A	120.0	N3A—C33A—C32A	123.10 (13)
C27A—C28A—H28B	120.0	N3A—C33A—H33A	118.5
H28A—C28A—H28B	120.0	C32A—C33A—H33A	118.5
C1B—O1B—H1OB	114.2 (14)	C29B—N3B—C33B	116.99 (12)
C2B—O2B—C25B	116.37 (10)	N3B—C29B—C30B	123.19 (14)
C16B—O3B—H3OB	115.7 (12)	N3B—C29B—H29B	118.4
C17B—O4B—C24B	117.47 (11)	C30B—C29B—H29B	118.4
C14B—N1B—C13B	105.63 (10)	C31B—C30B—C29B	118.87 (14)
C14B—N2B—C8B	107.01 (10)	C31B—C30B—H30B	120.6
C14B—N2B—C7B	128.51 (11)	C29B—C30B—H30B	120.6
C8B—N2B—C7B	123.89 (10)	C30B—C31B—C32B	118.73 (13)
O1B—C1B—C6B	117.52 (11)	C30B—C31B—H31B	120.6
O1B—C1B—C2B	123.21 (11)	C32B—C31B—H31B	120.6
C6B—C1B—C2B	119.26 (12)	C31B—C32B—C33B	118.71 (14)
O2B—C2B—C3B	125.24 (12)	C31B—C32B—H32B	120.6
O2B—C2B—C1B	114.37 (11)	C33B—C32B—H32B	120.6
C3B—C2B—C1B	120.38 (12)	N3B—C33B—C32B	123.51 (14)
C2B—C3B—C4B	120.69 (12)	N3B—C33B—H33B	118.2
C2B—C3B—H3B	119.7	C32B—C33B—H33B	118.2
C25A—O2A—C2A—C3A	4.29 (18)	O2B—C2B—C3B—C4B	178.77 (12)
C25A—O2A—C2A—C1A	−175.63 (11)	C1B—C2B—C3B—C4B	−0.66 (19)
O1A—C1A—C2A—O2A	−1.06 (17)	C2B—C3B—C4B—C5B	2.58 (19)
C6A—C1A—C2A—O2A	178.78 (11)	C2B—C3B—C4B—C26B	−178.20 (12)
O1A—C1A—C2A—C3A	179.02 (12)	C3B—C4B—C5B—C6B	−2.08 (19)
C6A—C1A—C2A—C3A	−1.14 (19)	C26B—C4B—C5B—C6B	178.70 (12)
O2A—C2A—C3A—C4A	−179.61 (12)	O1B—C1B—C6B—C5B	−177.44 (11)
C1A—C2A—C3A—C4A	0.30 (19)	C2B—C1B—C6B—C5B	2.29 (19)
C2A—C3A—C4A—C5A	0.31 (19)	O1B—C1B—C6B—C7B	0.45 (17)
C2A—C3A—C4A—C26A	−175.97 (12)	C2B—C1B—C6B—C7B	−179.81 (11)
C3A—C4A—C5A—C6A	−0.06 (19)	C4B—C5B—C6B—C1B	−0.35 (19)
C26A—C4A—C5A—C6A	176.26 (12)	C4B—C5B—C6B—C7B	−178.13 (12)
C4A—C5A—C6A—C1A	−0.78 (19)	C14B—N2B—C7B—C6B	87.21 (15)
C4A—C5A—C6A—C7A	−178.67 (12)	C8B—N2B—C7B—C6B	−82.87 (15)
O1A—C1A—C6A—C5A	−178.78 (11)	C1B—C6B—C7B—N2B	151.99 (11)
C2A—C1A—C6A—C5A	1.37 (18)	C5B—C6B—C7B—N2B	−30.18 (17)
O1A—C1A—C6A—C7A	−0.81 (17)	C14B—N2B—C8B—C9B	179.48 (14)
C2A—C1A—C6A—C7A	179.34 (11)	C7B—N2B—C8B—C9B	−8.6 (2)
C14A—N2A—C7A—C6A	93.27 (15)	C14B—N2B—C8B—C13B	0.48 (13)
C8A—N2A—C7A—C6A	−78.04 (15)	C7B—N2B—C8B—C13B	172.37 (11)
C5A—C6A—C7A—N2A	−35.08 (17)	N2B—C8B—C9B—C10B	−178.23 (13)
C1A—C6A—C7A—N2A	147.02 (11)	C13B—C8B—C9B—C10B	0.6 (2)
C14A—N2A—C8A—C9A	−179.57 (14)	C8B—C9B—C10B—C11B	−0.4 (2)
C7A—N2A—C8A—C9A	−6.6 (2)	C9B—C10B—C11B—C12B	0.3 (2)
C14A—N2A—C8A—C13A	0.75 (13)	C10B—C11B—C12B—C13B	−0.3 (2)
C7A—N2A—C8A—C13A	173.69 (11)	C14B—N1B—C13B—C12B	−178.45 (13)
N2A—C8A—C9A—C10A	−178.39 (13)	C14B—N1B—C13B—C8B	0.57 (14)
C13A—C8A—C9A—C10A	1.25 (19)	C11B—C12B—C13B—N1B	179.37 (13)
C8A—C9A—C10A—C11A	−0.1 (2)	C11B—C12B—C13B—C8B	0.44 (19)
C9A—C10A—C11A—C12A	−0.5 (2)	N2B—C8B—C13B—N1B	−0.66 (14)
C10A—C11A—C12A—C13A	0.0 (2)	C9B—C8B—C13B—N1B	−179.78 (12)
C14A—N1A—C13A—C12A	−177.93 (13)	N2B—C8B—C13B—C12B	178.48 (11)
C14A—N1A—C13A—C8A	0.91 (14)	C9B—C8B—C13B—C12B	−0.6 (2)
C11A—C12A—C13A—N1A	179.82 (13)	C13B—N1B—C14B—N2B	−0.27 (14)
C11A—C12A—C13A—C8A	1.09 (19)	C13B—N1B—C14B—C15B	−177.99 (11)
N2A—C8A—C13A—N1A	−1.03 (14)	C8B—N2B—C14B—N1B	−0.14 (14)
C9A—C8A—C13A—N1A	179.24 (12)	C7B—N2B—C14B—N1B	−171.53 (11)
N2A—C8A—C13A—C12A	177.93 (11)	C8B—N2B—C14B—C15B	177.54 (11)
C9A—C8A—C13A—C12A	−1.79 (19)	C7B—N2B—C14B—C15B	6.1 (2)
C13A—N1A—C14A—N2A	−0.43 (14)	N1B—C14B—C15B—C16B	−128.32 (14)
C13A—N1A—C14A—C15A	−177.57 (11)	N2B—C14B—C15B—C16B	54.24 (18)
C8A—N2A—C14A—N1A	−0.21 (14)	N1B—C14B—C15B—C20B	48.37 (17)
C7A—N2A—C14A—N1A	−172.67 (11)	N2B—C14B—C15B—C20B	−129.07 (13)
C8A—N2A—C14A—C15A	176.86 (11)	C20B—C15B—C16B—O3B	−177.02 (11)
C7A—N2A—C14A—C15A	4.4 (2)	C14B—C15B—C16B—O3B	−0.41 (19)
N1A—C14A—C15A—C16A	−129.32 (14)	C20B—C15B—C16B—C17B	1.92 (19)
N2A—C14A—C15A—C16A	53.91 (18)	C14B—C15B—C16B—C17B	178.53 (12)
N1A—C14A—C15A—C20A	47.43 (17)	C24B—O4B—C17B—C18B	12.40 (19)
N2A—C14A—C15A—C20A	−129.35 (13)	C24B—O4B—C17B—C16B	−169.18 (12)
C20A—C15A—C16A—O3A	−174.71 (11)	O3B—C16B—C17B—O4B	−1.57 (18)
C14A—C15A—C16A—O3A	1.95 (19)	C15B—C16B—C17B—O4B	179.51 (11)
C20A—C15A—C16A—C17A	5.15 (19)	O3B—C16B—C17B—C18B	176.93 (12)
C14A—C15A—C16A—C17A	−178.18 (12)	C15B—C16B—C17B—C18B	−1.99 (19)
C24A—O4A—C17A—C18A	6.52 (19)	O4B—C17B—C18B—C19B	179.27 (13)
C24A—O4A—C17A—C16A	−175.33 (11)	C16B—C17B—C18B—C19B	0.9 (2)
O3A—C16A—C17A—O4A	−3.82 (18)	C17B—C18B—C19B—C20B	0.2 (2)
C15A—C16A—C17A—O4A	176.31 (11)	C17B—C18B—C19B—C21B	179.51 (12)
O3A—C16A—C17A—C18A	174.42 (12)	C18B—C19B—C20B—C15B	−0.25 (19)
C15A—C16A—C17A—C18A	−5.44 (19)	C21B—C19B—C20B—C15B	−179.54 (12)
O4A—C17A—C18A—C19A	180.00 (12)	C16B—C15B—C20B—C19B	−0.83 (19)
C16A—C17A—C18A—C19A	2.0 (2)	C14B—C15B—C20B—C19B	−177.58 (12)
C17A—C18A—C19A—C20A	1.8 (2)	C20B—C19B—C21B—C22B	−8.9 (2)
C17A—C18A—C19A—C21A	−177.46 (12)	C18B—C19B—C21B—C22B	171.79 (12)
C18A—C19A—C20A—C15A	−2.07 (19)	C19B—C21B—C22B—C23B	124.11 (16)
C21A—C19A—C20A—C15A	177.17 (12)	C5B—C4B—C26B—C27B	97.42 (15)
C16A—C15A—C20A—C19A	−1.46 (19)	C3B—C4B—C26B—C27B	−81.78 (16)
C14A—C15A—C20A—C19A	−178.33 (12)	C4B—C26B—C27B—C28B	133.17 (15)
C20A—C19A—C21A—C22A	−10.9 (2)	C33A—N3A—C29A—C30A	−0.1 (2)
C18A—C19A—C21A—C22A	168.38 (12)	N3A—C29A—C30A—C31A	−0.2 (2)
C19A—C21A—C22A—C23A	134.61 (14)	C29A—C30A—C31A—C32A	0.6 (2)
C5A—C4A—C26A—C27A	−72.15 (16)	C30A—C31A—C32A—C33A	−0.6 (2)
C3A—C4A—C26A—C27A	104.09 (15)	C29A—N3A—C33A—C32A	0.1 (2)
C4A—C26A—C27A—C28A	107.50 (16)	C31A—C32A—C33A—N3A	0.2 (2)
C25B—O2B—C2B—C3B	2.11 (18)	C33B—N3B—C29B—C30B	0.9 (2)
C25B—O2B—C2B—C1B	−178.42 (11)	N3B—C29B—C30B—C31B	−0.3 (2)
O1B—C1B—C2B—O2B	−1.58 (18)	C29B—C30B—C31B—C32B	−0.5 (2)
C6B—C1B—C2B—O2B	178.70 (11)	C30B—C31B—C32B—C33B	0.6 (2)
O1B—C1B—C2B—C3B	177.92 (12)	C29B—N3B—C33B—C32B	−0.8 (2)
C6B—C1B—C2B—C3B	−1.80 (19)	C31B—C32B—C33B—N3B	0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O2A	0.93 (2)	2.30 (2)	2.6977 (14)	105 (1)
O1A—H1OA···N1B	0.93 (2)	1.81 (2)	2.6932 (15)	157 (2)
O3A—H3OA···O4A	0.93 (2)	2.25 (2)	2.6798 (13)	108 (2)
O3A—H3OA···N3B^i	0.93 (2)	1.90 (2)	2.7859 (14)	160 (2)
O1B—H1OB···O2B	0.90 (2)	2.33 (2)	2.7197 (14)	106 (2)
O1B—H1OB···N1A^ii	0.90 (2)	1.87 (2)	2.7114 (15)	153 (2)
O3B—H3OB···O4B	0.99 (2)	2.27 (2)	2.6789 (13)	103 (1)
O3B—H3OB···N3A^iii	0.99 (2)	1.68 (2)	2.6461 (15)	161 (2)
C7A—H7A···O3A	0.97	2.38	3.1017 (15)	131
C7A—H7B···O1A	0.97	2.35	2.7525 (16)	104
C7B—H7C···O3B	0.97	2.30	3.0302 (16)	132
C7B—H7D···O1B	0.97	2.35	2.7231 (16)	102
C11B—H11B···O2A^iv	0.93	2.59	3.5010 (17)	165
C31A—H31A···O1A	0.93	2.36	3.2382 (18)	158
C23A—H23A···Cg1^v	0.93	2.90	3.3950 (17)	115
C28B—H28C···Cg2^vi	0.93	2.99	3.4562 (18)	113
C33A—H33A···Cg3^i	0.93	2.74	3.4888 (16)	139

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