1-{[(Cyclo-hexyl-oxy)carbon-yl]-oxy}ethyl 3-{[2'-(2-ethyl-2H-tetra-zol-5-yl)biphenyl-4-yl]meth-yl}-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxyl-ate.

In the title compound, C(33)H(34)N(6)O(6), the dihydro-benzimidazol-2-one ring system is essentially planar (r.m.s. deviation = 0.021 Å). The cyclo-hexane ring adopts a chair conformation. In the 5-(biphenyl-2-yl)-2H-tetra-zole fragment, the tetra-zole ring is twisted away from the attached benzene ring by 35.73 (11)° and the two benzene rings form a dihedral angle of 68.00 (9)°. An intra-molecular C-H⋯O inter-action is observed. In the crystal, the mol-ecules are linked into a zigzag chain running along the b axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For applications of tetra­zole derivatives in coordination chemistry, medicinal chemistry and materials science, see: Dunica et al. (1991 ▶); Wittenberger & Donner (1993 ▶); Xiong et al. (2002 ▶); Xue et al. (2002 ▶). For metal-organic coordination compounds with tetra­zole ligands, see: Hu et al. (2007 ▶); Lü (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C33H34N6O6

M = 610.66

Monoclinic,

a = 16.3770 (7) Å

b = 8.5928 (4) Å

c = 43.7733 (19) Å

β = 91.150 (1)°

V = 6158.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.19 × 0.14 × 0.08 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.984, T max = 0.993

34307 measured reflections

7255 independent reflections

5559 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.143

S = 0.99

7255 reflections

412 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011049/ci5048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011049/ci5048Isup2.hkl

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

C33H34N6O6	F(000) = 2576
Mr = 610.66	Dx = 1.317 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3564 reflections
a = 16.3770 (7) Å	θ = 0.9–25.0°
b = 8.5928 (4) Å	µ = 0.09 mm−1
c = 43.7733 (19) Å	T = 293 K
β = 91.150 (1)°	Plate, colourless
V = 6158.7 (5) Å3	0.19 × 0.14 × 0.08 mm
Z = 8

Bruker Kappa APEXII area-detector diffractometer	7255 independent reflections
Radiation source: fine-focus sealed tube	5559 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −21→20
Tmin = 0.984, Tmax = 0.993	k = −11→11
34307 measured reflections	l = −56→57

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0675P)2 + 3.4615P] where P = (Fo2 + 2Fc2)/3
7255 reflections	(Δ/σ)max = 0.017
412 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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 > 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.

	x	y	z	Uiso*/Ueq
O1	−0.10538 (9)	0.40762 (15)	0.08077 (3)	0.0628 (3)
O2	−0.08267 (10)	0.24202 (17)	0.11988 (3)	0.0791 (4)
O3	−0.14741 (9)	0.47031 (16)	0.12506 (3)	0.0666 (4)
O4	−0.09830 (8)	0.58427 (14)	0.16718 (3)	0.0574 (3)
O5	−0.05644 (7)	0.45285 (14)	0.20880 (3)	0.0568 (3)
O6	0.24689 (8)	0.63668 (14)	0.25144 (3)	0.0567 (3)
C1	0.01658 (15)	0.3068 (4)	0.05704 (6)	0.1087 (10)
H1A	0.0403	0.2760	0.0766	0.130*
H1B	0.0329	0.4132	0.0530	0.130*
C2	0.04851 (15)	0.2007 (5)	0.03206 (7)	0.1128 (11)
H2A	0.1073	0.2125	0.0308	0.135*
H2B	0.0371	0.0932	0.0372	0.135*
C3	0.00998 (16)	0.2383 (3)	0.00197 (6)	0.0852 (7)
H3A	0.0286	0.1648	−0.0132	0.102*
H3B	0.0266	0.3417	−0.0043	0.102*
C4	−0.08144 (16)	0.2316 (3)	0.00346 (5)	0.0871 (7)
H4A	−0.0982	0.1255	0.0075	0.105*
H4B	−0.1050	0.2623	−0.0161	0.105*
C5	−0.11349 (14)	0.3378 (3)	0.02823 (5)	0.0725 (6)
H5A	−0.1020	0.4453	0.0231	0.087*
H5B	−0.1722	0.3258	0.0296	0.087*
C6	−0.07367 (11)	0.2981 (2)	0.05837 (4)	0.0570 (4)
H6	−0.0895	0.1923	0.0641	0.068*
C7	−0.10780 (11)	0.3606 (2)	0.10939 (4)	0.0528 (4)
C8	−0.14875 (11)	0.4568 (2)	0.15726 (4)	0.0564 (4)
H8	−0.1261	0.3569	0.1641	0.068*
C9	−0.23394 (14)	0.4783 (3)	0.16790 (5)	0.0839 (7)
H9A	−0.2553	0.5749	0.1601	0.126*
H9B	−0.2340	0.4800	0.1898	0.126*
H9C	−0.2674	0.3939	0.1606	0.126*
C10	−0.05646 (9)	0.56936 (19)	0.19372 (3)	0.0443 (3)
C11	−0.01429 (9)	0.71732 (18)	0.20158 (3)	0.0444 (3)
C12	−0.05366 (11)	0.8580 (2)	0.19443 (4)	0.0552 (4)
H12	−0.1034	0.8546	0.1838	0.066*
C13	−0.02180 (12)	1.0009 (2)	0.20246 (5)	0.0621 (5)
H13	−0.0505	1.0911	0.1975	0.074*
C14	0.05270 (12)	1.0113 (2)	0.21790 (4)	0.0572 (4)
H14	0.0748	1.1072	0.2234	0.069*
C15	0.09259 (10)	0.87500 (18)	0.22476 (4)	0.0452 (4)
N16	0.16694 (9)	0.85162 (16)	0.23946 (3)	0.0479 (3)
H16	0.1995 (13)	0.923 (2)	0.2449 (5)	0.064 (6)*
C17	0.18479 (10)	0.69756 (18)	0.24083 (3)	0.0444 (3)
N18	0.11883 (8)	0.62020 (14)	0.22739 (3)	0.0408 (3)
C19	0.06123 (9)	0.72809 (17)	0.21703 (3)	0.0401 (3)
C20	0.12542 (10)	0.45543 (17)	0.21919 (3)	0.0429 (3)
H20A	0.0729	0.4053	0.2217	0.052*
H20B	0.1646	0.4051	0.2328	0.052*
C21	0.15208 (9)	0.43559 (17)	0.18655 (4)	0.0424 (3)
C22	0.22015 (11)	0.5131 (2)	0.17578 (4)	0.0556 (4)
H22	0.2508	0.5756	0.1890	0.067*
C23	0.24300 (11)	0.4989 (2)	0.14583 (4)	0.0569 (4)
H23	0.2884	0.5532	0.1391	0.068*
C24	0.19952 (10)	0.40521 (19)	0.12553 (4)	0.0484 (4)
C25	0.13343 (12)	0.3242 (2)	0.13648 (4)	0.0572 (4)
H25	0.1046	0.2574	0.1235	0.069*
C26	0.10931 (11)	0.3405 (2)	0.16638 (4)	0.0538 (4)
H26	0.0637	0.2868	0.1730	0.065*
C27	0.22306 (10)	0.3941 (2)	0.09282 (4)	0.0502 (4)
C28	0.25473 (13)	0.2562 (2)	0.08167 (5)	0.0660 (5)
H28	0.2580	0.1695	0.0944	0.079*
C29	0.28138 (14)	0.2456 (3)	0.05206 (5)	0.0750 (6)
H29	0.3026	0.1522	0.0450	0.090*
C30	0.27686 (13)	0.3714 (3)	0.03306 (5)	0.0713 (6)
H30	0.2963	0.3645	0.0133	0.086*
C31	0.24339 (12)	0.5087 (2)	0.04329 (4)	0.0619 (5)
H31	0.2391	0.5936	0.0302	0.074*
C32	0.21603 (10)	0.5215 (2)	0.07304 (4)	0.0503 (4)
C33	0.17652 (10)	0.6676 (2)	0.08233 (4)	0.0518 (4)
N34	0.19874 (13)	0.8085 (2)	0.07278 (5)	0.0880 (6)
N35	0.14788 (13)	0.9081 (2)	0.08502 (6)	0.0919 (6)
N36	0.09842 (10)	0.82671 (19)	0.10133 (4)	0.0671 (4)
N37	0.11305 (11)	0.67617 (19)	0.10042 (4)	0.0722 (5)
C38	0.03020 (16)	0.8941 (3)	0.11829 (7)	0.0923 (8)
H38A	0.0323	0.8566	0.1392	0.111*
H38B	0.0356	1.0065	0.1187	0.111*
C39	−0.04796 (16)	0.8525 (3)	0.10426 (9)	0.1114 (10)
H39A	−0.0501	0.8894	0.0836	0.167*
H39B	−0.0912	0.8992	0.1155	0.167*
H39C	−0.0541	0.7414	0.1044	0.167*

	U11	U22	U33	U12	U13	U23
O1	0.0817 (9)	0.0544 (7)	0.0523 (7)	0.0067 (6)	0.0012 (6)	−0.0039 (6)
O2	0.1041 (11)	0.0636 (9)	0.0700 (9)	0.0226 (8)	0.0118 (8)	0.0078 (7)
O3	0.0888 (9)	0.0646 (8)	0.0459 (7)	0.0217 (7)	−0.0104 (6)	−0.0073 (6)
O4	0.0671 (8)	0.0548 (7)	0.0496 (7)	−0.0036 (6)	−0.0145 (6)	0.0028 (5)
O5	0.0632 (7)	0.0562 (7)	0.0505 (7)	−0.0091 (6)	−0.0077 (5)	0.0100 (6)
O6	0.0564 (7)	0.0507 (7)	0.0624 (7)	0.0044 (5)	−0.0168 (6)	−0.0005 (5)
C1	0.0600 (13)	0.180 (3)	0.0852 (17)	−0.0025 (16)	−0.0065 (12)	−0.0433 (19)
C2	0.0604 (14)	0.180 (3)	0.099 (2)	0.0255 (17)	0.0073 (13)	−0.036 (2)
C3	0.0959 (17)	0.0853 (16)	0.0755 (14)	0.0040 (13)	0.0323 (13)	−0.0007 (12)
C4	0.0925 (17)	0.1098 (19)	0.0588 (12)	0.0266 (14)	−0.0034 (11)	−0.0175 (12)
C5	0.0751 (13)	0.0808 (14)	0.0617 (12)	0.0164 (11)	0.0018 (10)	−0.0073 (10)
C6	0.0629 (11)	0.0526 (10)	0.0558 (10)	0.0027 (8)	0.0068 (8)	−0.0049 (8)
C7	0.0524 (9)	0.0496 (9)	0.0561 (10)	−0.0003 (8)	−0.0036 (8)	−0.0041 (8)
C8	0.0665 (11)	0.0564 (10)	0.0459 (9)	−0.0010 (8)	−0.0097 (8)	−0.0012 (8)
C9	0.0662 (13)	0.1121 (19)	0.0734 (14)	−0.0081 (13)	0.0012 (11)	−0.0025 (13)
C10	0.0421 (8)	0.0518 (9)	0.0390 (8)	0.0031 (7)	0.0011 (6)	0.0004 (7)
C11	0.0456 (8)	0.0462 (8)	0.0414 (8)	0.0030 (7)	0.0014 (6)	0.0023 (6)
C12	0.0525 (9)	0.0562 (10)	0.0565 (10)	0.0106 (8)	−0.0068 (8)	0.0040 (8)
C13	0.0672 (11)	0.0462 (9)	0.0726 (12)	0.0147 (8)	−0.0048 (9)	0.0080 (9)
C14	0.0693 (11)	0.0377 (8)	0.0644 (11)	0.0019 (8)	−0.0012 (9)	0.0035 (7)
C15	0.0501 (9)	0.0419 (8)	0.0438 (8)	−0.0007 (7)	0.0024 (7)	0.0034 (6)
N16	0.0503 (8)	0.0408 (7)	0.0525 (8)	−0.0040 (6)	−0.0022 (6)	−0.0014 (6)
C17	0.0500 (9)	0.0433 (8)	0.0399 (8)	0.0002 (7)	−0.0016 (6)	0.0012 (6)
N18	0.0466 (7)	0.0368 (6)	0.0390 (6)	0.0014 (5)	−0.0020 (5)	0.0026 (5)
C19	0.0457 (8)	0.0378 (7)	0.0368 (7)	0.0024 (6)	0.0033 (6)	0.0038 (6)
C20	0.0504 (8)	0.0340 (7)	0.0442 (8)	0.0024 (6)	−0.0052 (6)	0.0053 (6)
C21	0.0459 (8)	0.0346 (7)	0.0465 (8)	0.0050 (6)	−0.0045 (6)	0.0020 (6)
C22	0.0500 (9)	0.0607 (10)	0.0560 (10)	−0.0081 (8)	0.0003 (7)	−0.0154 (8)
C23	0.0474 (9)	0.0639 (11)	0.0599 (10)	−0.0083 (8)	0.0076 (8)	−0.0100 (9)
C24	0.0525 (9)	0.0432 (8)	0.0494 (9)	0.0071 (7)	−0.0006 (7)	−0.0021 (7)
C25	0.0700 (11)	0.0511 (10)	0.0503 (9)	−0.0139 (8)	−0.0077 (8)	−0.0038 (8)
C26	0.0619 (10)	0.0481 (9)	0.0513 (9)	−0.0131 (8)	−0.0023 (8)	0.0039 (7)
C27	0.0464 (8)	0.0534 (9)	0.0505 (9)	0.0043 (7)	−0.0017 (7)	−0.0078 (7)
C28	0.0738 (13)	0.0592 (11)	0.0649 (12)	0.0169 (10)	−0.0017 (10)	−0.0096 (9)
C29	0.0766 (13)	0.0744 (14)	0.0741 (14)	0.0201 (11)	0.0048 (11)	−0.0262 (11)
C30	0.0681 (12)	0.0905 (16)	0.0557 (11)	0.0045 (11)	0.0111 (9)	−0.0228 (11)
C31	0.0618 (11)	0.0720 (12)	0.0522 (10)	0.0010 (9)	0.0062 (8)	−0.0037 (9)
C32	0.0446 (8)	0.0547 (10)	0.0515 (9)	0.0012 (7)	0.0023 (7)	−0.0065 (7)
C33	0.0516 (9)	0.0529 (9)	0.0508 (9)	0.0010 (8)	0.0027 (7)	−0.0009 (7)
N34	0.0871 (13)	0.0578 (10)	0.1206 (17)	−0.0016 (10)	0.0389 (12)	0.0022 (11)
N35	0.0909 (14)	0.0528 (10)	0.1329 (19)	0.0002 (10)	0.0299 (13)	−0.0023 (11)
N36	0.0632 (9)	0.0525 (9)	0.0861 (12)	0.0072 (8)	0.0118 (8)	−0.0043 (8)
N37	0.0714 (10)	0.0525 (9)	0.0935 (13)	0.0126 (8)	0.0265 (9)	0.0053 (8)
C38	0.0877 (17)	0.0716 (14)	0.118 (2)	0.0227 (13)	0.0237 (15)	−0.0142 (14)
C39	0.0715 (16)	0.0864 (18)	0.177 (3)	0.0111 (14)	0.0266 (18)	−0.0051 (19)

O1—C7	1.318 (2)	N16—C17	1.357 (2)
O1—C6	1.462 (2)	N16—H16	0.85 (2)
O2—C7	1.188 (2)	C17—N18	1.389 (2)
O3—C7	1.341 (2)	N18—C19	1.3919 (19)
O3—C8	1.415 (2)	N18—C20	1.4652 (19)
O4—C10	1.3432 (18)	C20—C21	1.512 (2)
O4—C8	1.434 (2)	C20—H20A	0.97
O5—C10	1.1992 (19)	C20—H20B	0.97
O6—C17	1.2265 (19)	C21—C26	1.383 (2)
C1—C6	1.482 (3)	C21—C22	1.389 (2)
C1—C2	1.524 (4)	C22—C23	1.376 (2)
C1—H1A	0.97	C22—H22	0.93
C1—H1B	0.97	C23—C24	1.385 (2)
C2—C3	1.485 (4)	C23—H23	0.93
C2—H2A	0.97	C24—C25	1.381 (2)
C2—H2B	0.97	C24—C27	1.494 (2)
C3—C4	1.501 (4)	C25—C26	1.382 (3)
C3—H3A	0.97	C25—H25	0.93
C3—H3B	0.97	C26—H26	0.93
C4—C5	1.519 (3)	C27—C28	1.386 (2)
C4—H4A	0.97	C27—C32	1.399 (2)
C4—H4B	0.97	C28—C29	1.379 (3)
C5—C6	1.499 (3)	C28—H28	0.93
C5—H5A	0.97	C29—C30	1.365 (3)
C5—H5B	0.97	C29—H29	0.93
C6—H6	0.98	C30—C31	1.380 (3)
C8—C9	1.491 (3)	C30—H30	0.93
C8—H8	0.98	C31—C32	1.390 (2)
C9—H9A	0.96	C31—H31	0.93
C9—H9B	0.96	C32—C33	1.473 (2)
C9—H9C	0.96	C33—N37	1.321 (2)
C10—C11	1.484 (2)	C33—N34	1.334 (2)
C11—C19	1.401 (2)	N34—N35	1.316 (3)
C11—C12	1.402 (2)	N35—N36	1.296 (3)
C12—C13	1.377 (3)	N36—N37	1.316 (2)
C12—H12	0.93	N36—C38	1.472 (3)
C13—C14	1.386 (3)	C38—C39	1.453 (4)
C13—H13	0.93	C38—H38A	0.97
C14—C15	1.372 (2)	C38—H38B	0.97
C14—H14	0.93	C39—H39A	0.96
C15—N16	1.381 (2)	C39—H39B	0.96
C15—C19	1.402 (2)	C39—H39C	0.96
C7—O1—C6	117.26 (14)	C15—N16—H16	124.8 (14)
C7—O3—C8	117.98 (14)	O6—C17—N16	127.52 (15)
C10—O4—C8	118.04 (13)	O6—C17—N18	126.02 (14)
C6—C1—C2	110.8 (2)	N16—C17—N18	106.46 (13)
C6—C1—H1A	109.5	C17—N18—C19	109.60 (12)
C2—C1—H1A	109.5	C17—N18—C20	120.38 (13)
C6—C1—H1B	109.5	C19—N18—C20	128.06 (12)
C2—C1—H1B	109.5	N18—C19—C11	134.37 (14)
H1A—C1—H1B	108.1	N18—C19—C15	106.18 (13)
C3—C2—C1	111.2 (3)	C11—C19—C15	119.45 (14)
C3—C2—H2A	109.4	N18—C20—C21	111.38 (12)
C1—C2—H2A	109.4	N18—C20—H20A	109.4
C3—C2—H2B	109.4	C21—C20—H20A	109.4
C1—C2—H2B	109.4	N18—C20—H20B	109.4
H2A—C2—H2B	108.0	C21—C20—H20B	109.4
C2—C3—C4	111.1 (2)	H20A—C20—H20B	108.0
C2—C3—H3A	109.4	C26—C21—C22	117.78 (15)
C4—C3—H3A	109.4	C26—C21—C20	121.18 (14)
C2—C3—H3B	109.4	C22—C21—C20	121.04 (14)
C4—C3—H3B	109.4	C23—C22—C21	121.10 (16)
H3A—C3—H3B	108.0	C23—C22—H22	119.4
C3—C4—C5	111.6 (2)	C21—C22—H22	119.4
C3—C4—H4A	109.3	C22—C23—C24	121.07 (16)
C5—C4—H4A	109.3	C22—C23—H23	119.5
C3—C4—H4B	109.3	C24—C23—H23	119.5
C5—C4—H4B	109.3	C25—C24—C23	117.84 (16)
H4A—C4—H4B	108.0	C25—C24—C27	121.32 (15)
C6—C5—C4	109.95 (18)	C23—C24—C27	120.84 (16)
C6—C5—H5A	109.7	C24—C25—C26	121.24 (16)
C4—C5—H5A	109.7	C24—C25—H25	119.4
C6—C5—H5B	109.7	C26—C25—H25	119.4
C4—C5—H5B	109.7	C21—C26—C25	120.92 (16)
H5A—C5—H5B	108.2	C21—C26—H26	119.5
O1—C6—C1	111.23 (17)	C25—C26—H26	119.5
O1—C6—C5	106.85 (15)	C28—C27—C32	118.54 (17)
C1—C6—C5	111.75 (19)	C28—C27—C24	119.85 (16)
O1—C6—H6	109.0	C32—C27—C24	121.59 (15)
C1—C6—H6	109.0	C29—C28—C27	121.0 (2)
C5—C6—H6	109.0	C29—C28—H28	119.5
O2—C7—O1	127.88 (17)	C27—C28—H28	119.5
O2—C7—O3	124.95 (17)	C30—C29—C28	120.42 (19)
O1—C7—O3	107.13 (15)	C30—C29—H29	119.8
O3—C8—O4	102.64 (14)	C28—C29—H29	119.8
O3—C8—C9	109.53 (16)	C29—C30—C31	119.77 (19)
O4—C8—C9	110.35 (17)	C29—C30—H30	120.1
O3—C8—H8	111.3	C31—C30—H30	120.1
O4—C8—H8	111.3	C30—C31—C32	120.61 (19)
C9—C8—H8	111.3	C30—C31—H31	119.7
C8—C9—H9A	109.5	C32—C31—H31	119.7
C8—C9—H9B	109.5	C31—C32—C27	119.62 (16)
H9A—C9—H9B	109.5	C31—C32—C33	118.51 (17)
C8—C9—H9C	109.5	C27—C32—C33	121.80 (15)
H9A—C9—H9C	109.5	N37—C33—N34	111.09 (16)
H9B—C9—H9C	109.5	N37—C33—C32	124.63 (16)
O5—C10—O4	123.38 (15)	N34—C33—C32	124.25 (17)
O5—C10—C11	126.35 (14)	N35—N34—C33	106.52 (18)
O4—C10—C11	110.23 (13)	N36—N35—N34	106.30 (17)
C19—C11—C12	116.65 (15)	N35—N36—N37	113.45 (16)
C19—C11—C10	124.81 (14)	N35—N36—C38	123.69 (18)
C12—C11—C10	118.48 (14)	N37—N36—C38	122.82 (18)
C13—C12—C11	122.79 (16)	N36—N37—C33	102.65 (16)
C13—C12—H12	118.6	C39—C38—N36	111.2 (2)
C11—C12—H12	118.6	C39—C38—H38A	109.4
C12—C13—C14	120.48 (16)	N36—C38—H38A	109.4
C12—C13—H13	119.8	C39—C38—H38B	109.4
C14—C13—H13	119.8	N36—C38—H38B	109.4
C15—C14—C13	117.54 (16)	H38A—C38—H38B	108.0
C15—C14—H14	121.2	C38—C39—H39A	109.5
C13—C14—H14	121.2	C38—C39—H39B	109.5
C14—C15—N16	129.65 (15)	H39A—C39—H39B	109.5
C14—C15—C19	123.08 (15)	C38—C39—H39C	109.5
N16—C15—C19	107.27 (13)	H39A—C39—H39C	109.5
C17—N16—C15	110.47 (14)	H39B—C39—H39C	109.5
C17—N16—H16	124.4 (14)
C6—C1—C2—C3	55.9 (4)	N16—C15—C19—N18	−0.28 (17)
C1—C2—C3—C4	−55.3 (4)	C14—C15—C19—C11	0.0 (2)
C2—C3—C4—C5	55.8 (3)	N16—C15—C19—C11	−179.68 (14)
C3—C4—C5—C6	−55.5 (3)	C17—N18—C20—C21	−92.35 (16)
C7—O1—C6—C1	−85.6 (2)	C19—N18—C20—C21	70.00 (19)
C7—O1—C6—C5	152.22 (17)	N18—C20—C21—C26	−128.84 (15)
C2—C1—C6—O1	−176.0 (2)	N18—C20—C21—C22	50.8 (2)
C2—C1—C6—C5	−56.6 (3)	C26—C21—C22—C23	1.7 (3)
C4—C5—C6—O1	178.24 (19)	C20—C21—C22—C23	−177.95 (16)
C4—C5—C6—C1	56.4 (3)	C21—C22—C23—C24	−0.9 (3)
C6—O1—C7—O2	5.0 (3)	C22—C23—C24—C25	−1.2 (3)
C6—O1—C7—O3	−172.79 (15)	C22—C23—C24—C27	178.11 (17)
C8—O3—C7—O2	10.3 (3)	C23—C24—C25—C26	2.5 (3)
C8—O3—C7—O1	−171.84 (15)	C27—C24—C25—C26	−176.77 (16)
C7—O3—C8—O4	110.92 (17)	C22—C21—C26—C25	−0.3 (3)
C7—O3—C8—C9	−131.85 (19)	C20—C21—C26—C25	179.28 (15)
C10—O4—C8—O3	−150.40 (14)	C24—C25—C26—C21	−1.8 (3)
C10—O4—C8—C9	92.95 (19)	C25—C24—C27—C28	−68.9 (2)
C8—O4—C10—O5	3.3 (2)	C23—C24—C27—C28	111.8 (2)
C8—O4—C10—C11	−174.68 (14)	C25—C24—C27—C32	112.8 (2)
O5—C10—C11—C19	35.4 (3)	C23—C24—C27—C32	−66.5 (2)
O4—C10—C11—C19	−146.73 (15)	C32—C27—C28—C29	2.2 (3)
O5—C10—C11—C12	−141.61 (18)	C24—C27—C28—C29	−176.16 (18)
O4—C10—C11—C12	36.3 (2)	C27—C28—C29—C30	−0.2 (3)
C19—C11—C12—C13	−1.3 (3)	C28—C29—C30—C31	−1.7 (3)
C10—C11—C12—C13	175.95 (17)	C29—C30—C31—C32	1.6 (3)
C11—C12—C13—C14	0.9 (3)	C30—C31—C32—C27	0.4 (3)
C12—C13—C14—C15	−0.1 (3)	C30—C31—C32—C33	−176.57 (17)
C13—C14—C15—N16	179.23 (17)	C28—C27—C32—C31	−2.3 (3)
C13—C14—C15—C19	−0.4 (3)	C24—C27—C32—C31	176.01 (16)
C14—C15—N16—C17	−178.38 (18)	C28—C27—C32—C33	174.63 (16)
C19—C15—N16—C17	1.28 (18)	C24—C27—C32—C33	−7.1 (2)
C15—N16—C17—O6	177.55 (16)	C31—C32—C33—N37	141.6 (2)
C15—N16—C17—N18	−1.74 (17)	C27—C32—C33—N37	−35.3 (3)
O6—C17—N18—C19	−177.75 (15)	C31—C32—C33—N34	−36.2 (3)
N16—C17—N18—C19	1.55 (17)	C27—C32—C33—N34	146.8 (2)
O6—C17—N18—C20	−12.4 (2)	N37—C33—N34—N35	−0.3 (3)
N16—C17—N18—C20	166.86 (13)	C32—C33—N34—N35	177.82 (19)
C17—N18—C19—C11	178.49 (16)	C33—N34—N35—N36	0.5 (3)
C20—N18—C19—C11	14.6 (3)	N34—N35—N36—N37	−0.6 (3)
C17—N18—C19—C15	−0.78 (16)	N34—N35—N36—C38	−178.2 (2)
C20—N18—C19—C15	−164.66 (14)	N35—N36—N37—C33	0.5 (3)
C12—C11—C19—N18	−178.42 (16)	C38—N36—N37—C33	178.1 (2)
C10—C11—C19—N18	4.6 (3)	N34—C33—N37—N36	−0.1 (2)
C12—C11—C19—C15	0.8 (2)	C32—C33—N37—N36	−178.19 (17)
C10—C11—C19—C15	−176.23 (14)	N35—N36—C38—C39	109.2 (3)
C14—C15—C19—N18	179.41 (16)	N37—N36—C38—C39	−68.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16···O6i	0.85 (2)	2.04 (2)	2.8508 (19)	161 (2)
C20—H20A···O5	0.97	2.22	3.004 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N16—H16⋯O6i	0.85 (2)	2.04 (2)	2.8508 (19)	161 (2)
C20—H20A⋯O5	0.97	2.22	3.004 (2)	137

Symmetry code: (i) .