7,7'-(3,3'-Dibenzyl-3H,3'H-4,4'-bi-1,2,3-triazole-5,5'-di-yl)bis-(4-methyl-2H-chromen-2-one).

The title compound, a bis-5,5'-triazole, C(38)H(28)N(6)O(4), was observed as a side-product from the Sharpless-Meldal click reaction of the corresponding coumarin alkyne and benzyl-azide. Although the compound was present as a minor component, it crystallized in preference to the major product. The two triazole rings are almost orthogonal to each other [dihedral angle = 83.8 (1)°]. However the 4 and 4' coumarin systems are close to coplanar with their respective triazole rings [23.6 (1) and 15.1 (1)°]. Each of the benzene rings packs approximately face-to-face with the opposing coumarin ring systems, with inter-planar angles of 7.7 (1) and 25.3 (1)° and distances of 3.567 (2) and 3.929 (2) Å between the respective centroids of the opposing rings.

Related literature

Similar 5,5′-bis­triazole structures have been described previously by Angell & Burgess (2007 ▶). For the synthesis of related alkyne-modified coumarins, see: Sivakumar et al. (2004 ▶); Zhou & Fahrni (2004 ▶).

Experimental

Crystal data

C38H28N6O4

M = 632.66

Monoclinic,

a = 12.4328 (17) Å

b = 17.565 (2) Å

c = 14.456 (2) Å

β = 94.573 (3)°

V = 3147.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 193 (2) K

0.36 × 0.19 × 0.06 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.969, T max = 0.995

21410 measured reflections

5703 independent reflections

3222 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.114

S = 1.00

5703 reflections

435 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028250/fb2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028250/fb2110Isup2.hkl

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

C38H28N6O4	F(000) = 1320
Mr = 632.66	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2863 reflections
a = 12.4328 (17) Å	θ = 2.3–20.4°
b = 17.565 (2) Å	µ = 0.09 mm−1
c = 14.456 (2) Å	T = 193 K
β = 94.573 (3)°	Plate, colourless
V = 3147.0 (7) Å3	0.36 × 0.19 × 0.06 mm
Z = 4

Bruker PLATFORM diffractometer/SMART 1000 CCD area-detector	5703 independent reflections
Radiation source: fine-focus sealed tube	3222 reflections with I > 2σ(I)
graphite	Rint = 0.074
Detector resolution: 8.192 pixels mm-1	θmax = 25.3°, θmin = 1.6°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −21→21
Tmin = 0.969, Tmax = 0.995	l = −17→17
21410 measured reflections

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.7089P] where P = (Fo2 + 2Fc2)/3
5703 reflections	(Δ/σ)max < 0.001
435 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3
110 constraints

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.

	x	y	z	Uiso*/Ueq
O1	−0.04554 (13)	0.38038 (9)	0.61080 (10)	0.0487 (4)
O2	−0.11506 (15)	0.35827 (9)	0.74362 (12)	0.0611 (5)
O3	0.40923 (16)	0.24278 (11)	0.23341 (13)	0.0765 (6)
O4	0.5627 (2)	0.20011 (15)	0.29991 (18)	0.1143 (9)
N1	0.22902 (15)	0.49591 (11)	0.24171 (13)	0.0435 (5)
N2	0.27468 (17)	0.50775 (12)	0.32747 (14)	0.0529 (6)
N3	0.21771 (16)	0.47016 (11)	0.38566 (13)	0.0493 (5)
N4	−0.01392 (15)	0.46189 (10)	0.12514 (12)	0.0399 (5)
N5	−0.05450 (16)	0.42958 (11)	0.04549 (13)	0.0460 (5)
N6	0.00981 (16)	0.37304 (11)	0.02675 (13)	0.0441 (5)
C1	−0.1166 (2)	0.34162 (14)	0.66209 (18)	0.0479 (6)
C2	−0.18458 (19)	0.28631 (13)	0.61442 (17)	0.0471 (6)
H2	−0.2375	0.2616	0.6476	0.056*
C3	−0.17758 (19)	0.26742 (13)	0.52525 (17)	0.0431 (6)
C4	−0.09753 (18)	0.30559 (12)	0.47449 (15)	0.0389 (6)
C5	−0.0778 (2)	0.28938 (13)	0.38278 (16)	0.0466 (6)
H5	−0.1172	0.2498	0.3507	0.056*
C6	−0.00257 (19)	0.32950 (13)	0.33810 (16)	0.0455 (6)
H6	0.0097	0.3171	0.2759	0.055*
C7	0.05606 (18)	0.38843 (12)	0.38319 (15)	0.0381 (6)
C8	0.03910 (18)	0.40452 (12)	0.47489 (15)	0.0407 (6)
H8	0.0785	0.4440	0.5071	0.049*
C9	−0.03566 (18)	0.36255 (13)	0.51869 (15)	0.0392 (6)
C10	−0.2493 (2)	0.20886 (15)	0.47772 (18)	0.0610 (8)
H10A	−0.2972	0.1877	0.5219	0.073*
H10B	−0.2052	0.1680	0.4543	0.073*
H10C	−0.2927	0.2324	0.4258	0.073*
C11	0.13516 (18)	0.43373 (12)	0.33611 (15)	0.0392 (6)
C12	0.14149 (18)	0.44964 (12)	0.24347 (15)	0.0368 (5)
C13	0.27160 (19)	0.53422 (14)	0.16239 (16)	0.0487 (7)
H13A	0.3156	0.5784	0.1852	0.058*
H13B	0.2105	0.5539	0.1211	0.058*
C14	0.33957 (19)	0.48340 (14)	0.10704 (18)	0.0476 (6)
C15	0.3150 (2)	0.47500 (15)	0.01346 (18)	0.0556 (7)
H15	0.2546	0.5013	−0.0155	0.067*
C16	0.3761 (2)	0.42923 (18)	−0.0396 (2)	0.0715 (9)
H16	0.3577	0.4244	−0.1044	0.086*
C17	0.4629 (3)	0.39096 (18)	0.0011 (3)	0.0779 (10)
H17	0.5043	0.3586	−0.0349	0.094*
C18	0.4899 (2)	0.3996 (2)	0.0946 (3)	0.0861 (10)
H18	0.5512	0.3738	0.1228	0.103*
C19	0.4289 (2)	0.44567 (18)	0.1482 (2)	0.0715 (9)
H19	0.4482	0.4513	0.2128	0.086*
C21	0.5019 (3)	0.19979 (19)	0.2306 (3)	0.0810 (10)
C22	0.5171 (2)	0.16063 (18)	0.1459 (3)	0.0800 (10)
H22	0.5796	0.1299	0.1431	0.096*
C23	0.4479 (2)	0.16503 (17)	0.0704 (2)	0.0717 (9)
C24	0.3521 (2)	0.21249 (15)	0.07429 (19)	0.0562 (7)
C25	0.2752 (2)	0.22437 (16)	0.0006 (2)	0.0631 (8)
H25	0.2817	0.1980	−0.0561	0.076*
C26	0.1900 (2)	0.27323 (14)	0.00755 (18)	0.0528 (7)
H26	0.1389	0.2806	−0.0441	0.063*
C27	0.17829 (19)	0.31216 (13)	0.09072 (16)	0.0431 (6)
C28	0.2519 (2)	0.29845 (14)	0.16581 (17)	0.0512 (7)
H28	0.2434	0.3224	0.2237	0.061*
C29	0.3372 (2)	0.25008 (15)	0.15623 (19)	0.0537 (7)
C30	0.4669 (3)	0.1241 (2)	−0.0173 (2)	0.1060 (13)
H30A	0.5311	0.0919	−0.0072	0.127*
H30B	0.4779	0.1613	−0.0663	0.127*
H30C	0.4042	0.0924	−0.0361	0.127*
C31	0.09201 (18)	0.36899 (13)	0.09483 (15)	0.0382 (6)
C32	0.07816 (17)	0.42608 (12)	0.15855 (15)	0.0364 (5)
C33	−0.07212 (19)	0.52408 (13)	0.16521 (17)	0.0481 (6)
H33A	−0.1075	0.5553	0.1145	0.058*
H33B	−0.0200	0.5570	0.2018	0.058*
C34	−0.1562 (2)	0.49688 (16)	0.22682 (16)	0.0492 (7)
C35	−0.1863 (3)	0.5442 (2)	0.2960 (2)	0.0877 (11)
H35	−0.1547	0.5933	0.3036	0.105*
C36	−0.2617 (3)	0.5209 (3)	0.3541 (3)	0.1298 (18)
H36	−0.2814	0.5536	0.4022	0.156*
C37	−0.3088 (3)	0.4506 (3)	0.3432 (3)	0.1210 (17)
H37	−0.3612	0.4349	0.3837	0.145*
C38	−0.2809 (3)	0.4032 (2)	0.2748 (2)	0.0917 (11)
H38	−0.3137	0.3546	0.2667	0.110*
C39	−0.2042 (2)	0.42693 (18)	0.2171 (2)	0.0676 (8)
H39	−0.1842	0.3938	0.1694	0.081*

	U11	U22	U33	U12	U13	U23
O1	0.0625 (12)	0.0467 (10)	0.0383 (10)	−0.0123 (9)	0.0128 (9)	−0.0055 (8)
O2	0.0865 (14)	0.0564 (11)	0.0424 (11)	−0.0080 (10)	0.0177 (10)	−0.0004 (9)
O3	0.0629 (13)	0.0901 (15)	0.0732 (14)	0.0306 (11)	−0.0150 (11)	−0.0122 (11)
O4	0.0845 (18)	0.139 (2)	0.112 (2)	0.0492 (16)	−0.0406 (16)	−0.0220 (16)
N1	0.0425 (12)	0.0502 (12)	0.0374 (12)	−0.0082 (10)	0.0017 (10)	0.0042 (10)
N2	0.0550 (14)	0.0602 (14)	0.0424 (13)	−0.0147 (11)	−0.0027 (11)	0.0027 (11)
N3	0.0523 (13)	0.0551 (13)	0.0399 (12)	−0.0127 (11)	0.0001 (11)	0.0015 (10)
N4	0.0404 (12)	0.0449 (12)	0.0346 (11)	0.0009 (10)	0.0040 (9)	−0.0021 (9)
N5	0.0431 (12)	0.0550 (13)	0.0394 (12)	0.0023 (11)	0.0005 (10)	−0.0043 (10)
N6	0.0412 (12)	0.0510 (13)	0.0402 (12)	0.0007 (10)	0.0041 (10)	−0.0037 (10)
C1	0.0574 (17)	0.0426 (15)	0.0453 (16)	0.0012 (13)	0.0138 (14)	0.0065 (13)
C2	0.0447 (15)	0.0447 (15)	0.0531 (17)	−0.0056 (12)	0.0114 (13)	0.0038 (13)
C3	0.0409 (15)	0.0391 (14)	0.0489 (16)	−0.0003 (11)	0.0011 (13)	0.0037 (12)
C4	0.0406 (14)	0.0353 (13)	0.0404 (15)	−0.0026 (11)	0.0015 (12)	0.0006 (11)
C5	0.0547 (17)	0.0436 (14)	0.0410 (15)	−0.0109 (13)	−0.0008 (13)	−0.0043 (12)
C6	0.0561 (16)	0.0476 (15)	0.0330 (14)	−0.0081 (13)	0.0046 (12)	−0.0033 (12)
C7	0.0397 (14)	0.0379 (14)	0.0363 (14)	0.0004 (11)	0.0012 (11)	0.0023 (11)
C8	0.0479 (15)	0.0370 (13)	0.0372 (14)	−0.0084 (11)	0.0026 (12)	−0.0043 (11)
C9	0.0446 (15)	0.0386 (14)	0.0345 (14)	0.0011 (12)	0.0041 (12)	−0.0010 (11)
C10	0.0523 (17)	0.0643 (18)	0.0657 (19)	−0.0200 (14)	0.0005 (14)	0.0008 (15)
C11	0.0421 (14)	0.0406 (14)	0.0344 (14)	−0.0030 (11)	0.0007 (12)	−0.0031 (11)
C12	0.0360 (14)	0.0363 (13)	0.0381 (14)	−0.0015 (11)	0.0036 (11)	0.0005 (11)
C13	0.0465 (15)	0.0547 (16)	0.0452 (15)	−0.0101 (13)	0.0066 (12)	0.0112 (12)
C14	0.0345 (14)	0.0573 (17)	0.0516 (17)	−0.0077 (12)	0.0069 (13)	0.0111 (13)
C15	0.0486 (17)	0.0635 (18)	0.0550 (18)	−0.0015 (14)	0.0052 (14)	0.0027 (14)
C16	0.065 (2)	0.085 (2)	0.066 (2)	−0.0007 (18)	0.0158 (17)	−0.0099 (17)
C17	0.063 (2)	0.078 (2)	0.098 (3)	0.0030 (18)	0.038 (2)	0.003 (2)
C18	0.050 (2)	0.105 (3)	0.105 (3)	0.0202 (18)	0.020 (2)	0.028 (2)
C19	0.0469 (18)	0.102 (2)	0.066 (2)	0.0033 (17)	0.0075 (16)	0.0221 (18)
C21	0.056 (2)	0.090 (2)	0.094 (3)	0.0247 (18)	−0.015 (2)	−0.013 (2)
C22	0.0467 (19)	0.085 (2)	0.107 (3)	0.0192 (17)	0.002 (2)	−0.019 (2)
C23	0.0444 (18)	0.078 (2)	0.093 (2)	0.0118 (16)	0.0065 (18)	−0.0228 (18)
C24	0.0391 (16)	0.0618 (18)	0.0676 (19)	0.0048 (13)	0.0034 (15)	−0.0201 (15)
C25	0.0468 (17)	0.078 (2)	0.0645 (19)	0.0038 (15)	0.0040 (15)	−0.0303 (16)
C26	0.0409 (16)	0.0644 (18)	0.0525 (16)	0.0019 (13)	0.0008 (13)	−0.0155 (14)
C27	0.0366 (14)	0.0470 (15)	0.0465 (16)	−0.0010 (12)	0.0077 (12)	−0.0043 (12)
C28	0.0515 (17)	0.0579 (17)	0.0440 (16)	0.0123 (14)	0.0022 (13)	−0.0056 (13)
C29	0.0421 (16)	0.0593 (17)	0.0580 (17)	0.0070 (14)	−0.0062 (14)	−0.0075 (14)
C30	0.067 (2)	0.133 (3)	0.119 (3)	0.039 (2)	0.010 (2)	−0.050 (3)
C31	0.0336 (13)	0.0461 (14)	0.0349 (13)	−0.0026 (11)	0.0030 (12)	0.0006 (11)
C32	0.0331 (13)	0.0413 (14)	0.0348 (13)	−0.0030 (11)	0.0035 (11)	0.0029 (11)
C33	0.0495 (16)	0.0463 (15)	0.0480 (15)	0.0070 (12)	−0.0002 (13)	−0.0058 (12)
C34	0.0443 (15)	0.0636 (18)	0.0394 (15)	0.0143 (14)	0.0004 (12)	0.0009 (13)
C35	0.064 (2)	0.127 (3)	0.074 (2)	0.009 (2)	0.0146 (18)	−0.041 (2)
C36	0.081 (3)	0.230 (6)	0.082 (3)	0.004 (3)	0.032 (2)	−0.061 (3)
C37	0.073 (3)	0.220 (6)	0.075 (3)	−0.006 (3)	0.037 (2)	0.009 (3)
C38	0.071 (2)	0.123 (3)	0.085 (3)	0.004 (2)	0.029 (2)	0.025 (2)
C39	0.065 (2)	0.074 (2)	0.067 (2)	0.0103 (17)	0.0268 (16)	0.0103 (16)

O1—C1	1.378 (3)	C15—H15	0.9500
O1—C9	1.383 (2)	C16—C17	1.364 (4)
O2—C1	1.213 (3)	C16—H16	0.9500
O3—C29	1.380 (3)	C17—C18	1.374 (4)
O3—C21	1.381 (3)	C17—H17	0.9500
O4—C21	1.206 (3)	C18—C19	1.388 (4)
N1—N2	1.338 (2)	C18—H18	0.9500
N1—C12	1.360 (3)	C19—H19	0.9500
N1—C13	1.465 (3)	C21—C22	1.431 (4)
N2—N3	1.319 (2)	C22—C23	1.337 (4)
N3—C11	1.363 (3)	C22—H22	0.9500
N4—N5	1.345 (2)	C23—C24	1.459 (4)
N4—C32	1.361 (3)	C23—C30	1.493 (4)
N4—C33	1.456 (3)	C24—C29	1.381 (3)
N5—N6	1.317 (2)	C24—C25	1.390 (3)
N6—C31	1.363 (3)	C25—C26	1.374 (3)
C1—C2	1.428 (3)	C25—H25	0.9500
C2—C3	1.341 (3)	C26—C27	1.401 (3)
C2—H2	0.9500	C26—H26	0.9500
C3—C4	1.447 (3)	C27—C28	1.384 (3)
C3—C10	1.493 (3)	C27—C31	1.470 (3)
C4—C9	1.387 (3)	C28—C29	1.375 (3)
C4—C5	1.397 (3)	C28—H28	0.9500
C5—C6	1.373 (3)	C30—H30A	0.9800
C5—H5	0.9500	C30—H30B	0.9800
C6—C7	1.397 (3)	C30—H30C	0.9800
C6—H6	0.9500	C31—C32	1.382 (3)
C7—C8	1.388 (3)	C33—C34	1.504 (3)
C7—C11	1.473 (3)	C33—H33A	0.9900
C8—C9	1.379 (3)	C33—H33B	0.9900
C8—H8	0.9500	C34—C39	1.368 (4)
C10—H10A	0.9800	C34—C35	1.376 (4)
C10—H10B	0.9800	C35—C36	1.370 (5)
C10—H10C	0.9800	C35—H35	0.9500
C11—C12	1.376 (3)	C36—C37	1.371 (6)
C12—C32	1.464 (3)	C36—H36	0.9500
C13—C14	1.503 (3)	C37—C38	1.359 (5)
C13—H13A	0.9900	C37—H37	0.9500
C13—H13B	0.9900	C38—C39	1.381 (4)
C14—C15	1.371 (3)	C38—H38	0.9500
C14—C19	1.387 (4)	C39—H39	0.9500
C15—C16	1.380 (4)
C1—O1—C9	121.08 (19)	C17—C18—C19	120.8 (3)
C29—O3—C21	121.1 (2)	C17—C18—H18	119.6
N2—N1—C12	110.89 (18)	C19—C18—H18	119.6
N2—N1—C13	120.06 (19)	C14—C19—C18	119.6 (3)
C12—N1—C13	129.0 (2)	C14—C19—H19	120.2
N3—N2—N1	107.66 (18)	C18—C19—H19	120.2
N2—N3—C11	108.65 (18)	O4—C21—O3	116.3 (3)
N5—N4—C32	110.87 (18)	O4—C21—C22	126.7 (3)
N5—N4—C33	119.52 (19)	O3—C21—C22	117.1 (3)
C32—N4—C33	129.53 (19)	C23—C22—C21	123.4 (3)
N6—N5—N4	107.57 (18)	C23—C22—H22	118.3
N5—N6—C31	108.87 (18)	C21—C22—H22	118.3
O2—C1—O1	116.3 (2)	C22—C23—C24	118.4 (3)
O2—C1—C2	126.6 (2)	C22—C23—C30	122.1 (3)
O1—C1—C2	117.2 (2)	C24—C23—C30	119.5 (3)
C3—C2—C1	123.4 (2)	C29—C24—C25	117.1 (2)
C3—C2—H2	118.3	C29—C24—C23	118.2 (3)
C1—C2—H2	118.3	C25—C24—C23	124.8 (3)
C2—C3—C4	118.2 (2)	C26—C25—C24	121.7 (2)
C2—C3—C10	122.1 (2)	C26—C25—H25	119.2
C4—C3—C10	119.7 (2)	C24—C25—H25	119.2
C9—C4—C5	116.8 (2)	C25—C26—C27	120.1 (2)
C9—C4—C3	118.6 (2)	C25—C26—H26	119.9
C5—C4—C3	124.5 (2)	C27—C26—H26	120.0
C6—C5—C4	121.3 (2)	C28—C27—C26	118.8 (2)
C6—C5—H5	119.3	C28—C27—C31	121.7 (2)
C4—C5—H5	119.3	C26—C27—C31	119.5 (2)
C5—C6—C7	120.7 (2)	C29—C28—C27	119.7 (2)
C5—C6—H6	119.7	C29—C28—H28	120.1
C7—C6—H6	119.7	C27—C28—H28	120.1
C8—C7—C6	118.9 (2)	C28—C29—O3	115.6 (2)
C8—C7—C11	119.3 (2)	C28—C29—C24	122.6 (2)
C6—C7—C11	121.8 (2)	O3—C29—C24	121.8 (2)
C9—C8—C7	119.3 (2)	C23—C30—H30A	109.5
C9—C8—H8	120.4	C23—C30—H30B	109.5
C7—C8—H8	120.4	H30A—C30—H30B	109.5
C8—C9—O1	115.8 (2)	C23—C30—H30C	109.5
C8—C9—C4	122.9 (2)	H30A—C30—H30C	109.5
O1—C9—C4	121.2 (2)	H30B—C30—H30C	109.5
C3—C10—H10A	109.5	N6—C31—C32	108.5 (2)
C3—C10—H10B	109.5	N6—C31—C27	120.9 (2)
H10A—C10—H10B	109.5	C32—C31—C27	130.5 (2)
C3—C10—H10C	109.5	N4—C32—C31	104.18 (19)
H10A—C10—H10C	109.5	N4—C32—C12	123.2 (2)
H10B—C10—H10C	109.5	C31—C32—C12	132.6 (2)
N3—C11—C12	108.5 (2)	N4—C33—C34	112.85 (19)
N3—C11—C7	120.9 (2)	N4—C33—H33A	109.0
C12—C11—C7	130.6 (2)	C34—C33—H33A	109.0
N1—C12—C11	104.33 (19)	N4—C33—H33B	109.0
N1—C12—C32	122.06 (19)	C34—C33—H33B	109.0
C11—C12—C32	133.6 (2)	H33A—C33—H33B	107.8
N1—C13—C14	113.43 (19)	C39—C34—C35	118.4 (3)
N1—C13—H13A	108.9	C39—C34—C33	122.8 (2)
C14—C13—H13A	108.9	C35—C34—C33	118.7 (3)
N1—C13—H13B	108.9	C36—C35—C34	120.2 (4)
C14—C13—H13B	108.9	C36—C35—H35	119.9
H13A—C13—H13B	107.7	C34—C35—H35	119.9
C15—C14—C19	118.7 (3)	C35—C36—C37	120.5 (4)
C15—C14—C13	119.9 (2)	C35—C36—H36	119.8
C19—C14—C13	121.4 (2)	C37—C36—H36	119.8
C14—C15—C16	121.5 (3)	C38—C37—C36	120.2 (4)
C14—C15—H15	119.3	C38—C37—H37	119.9
C16—C15—H15	119.3	C36—C37—H37	119.9
C17—C16—C15	119.9 (3)	C37—C38—C39	119.0 (4)
C17—C16—H16	120.0	C37—C38—H38	120.5
C15—C16—H16	120.0	C39—C38—H38	120.5
C16—C17—C18	119.5 (3)	C34—C39—C38	121.7 (3)
C16—C17—H17	120.3	C34—C39—H39	119.2
C18—C17—H17	120.3	C38—C39—H39	119.2
C12—N1—N2—N3	−0.4 (3)	C17—C18—C19—C14	0.0 (5)
C13—N1—N2—N3	176.64 (19)	C29—O3—C21—O4	176.2 (3)
N1—N2—N3—C11	0.3 (3)	C29—O3—C21—C22	−2.8 (4)
C32—N4—N5—N6	0.2 (2)	O4—C21—C22—C23	−177.5 (4)
C33—N4—N5—N6	−176.94 (18)	O3—C21—C22—C23	1.4 (5)
N4—N5—N6—C31	0.1 (2)	C21—C22—C23—C24	0.3 (5)
C9—O1—C1—O2	175.8 (2)	C21—C22—C23—C30	179.2 (3)
C9—O1—C1—C2	−4.3 (3)	C22—C23—C24—C29	−0.5 (4)
O2—C1—C2—C3	−175.8 (3)	C30—C23—C24—C29	−179.5 (3)
O1—C1—C2—C3	4.3 (4)	C22—C23—C24—C25	177.9 (3)
C1—C2—C3—C4	−0.5 (4)	C30—C23—C24—C25	−1.1 (5)
C1—C2—C3—C10	179.5 (2)	C29—C24—C25—C26	2.1 (4)
C2—C3—C4—C9	−3.3 (3)	C23—C24—C25—C26	−176.3 (3)
C10—C3—C4—C9	176.7 (2)	C24—C25—C26—C27	−0.5 (4)
C2—C3—C4—C5	177.0 (2)	C25—C26—C27—C28	−2.1 (4)
C10—C3—C4—C5	−3.0 (4)	C25—C26—C27—C31	174.9 (2)
C9—C4—C5—C6	−1.6 (3)	C26—C27—C28—C29	3.1 (4)
C3—C4—C5—C6	178.1 (2)	C31—C27—C28—C29	−173.9 (2)
C4—C5—C6—C7	−0.5 (4)	C27—C28—C29—O3	177.0 (2)
C5—C6—C7—C8	1.7 (3)	C27—C28—C29—C24	−1.5 (4)
C5—C6—C7—C11	−178.3 (2)	C21—O3—C29—C28	−175.8 (3)
C6—C7—C8—C9	−0.6 (3)	C21—O3—C29—C24	2.7 (4)
C11—C7—C8—C9	179.4 (2)	C25—C24—C29—C28	−1.1 (4)
C7—C8—C9—O1	178.1 (2)	C23—C24—C29—C28	177.4 (3)
C7—C8—C9—C4	−1.7 (3)	C25—C24—C29—O3	−179.4 (2)
C1—O1—C9—C8	−179.2 (2)	C23—C24—C29—O3	−1.0 (4)
C1—O1—C9—C4	0.6 (3)	N5—N6—C31—C32	−0.3 (2)
C5—C4—C9—C8	2.8 (3)	N5—N6—C31—C27	−178.29 (19)
C3—C4—C9—C8	−177.0 (2)	C28—C27—C31—N6	−168.9 (2)
C5—C4—C9—O1	−176.9 (2)	C26—C27—C31—N6	14.2 (3)
C3—C4—C9—O1	3.3 (3)	C28—C27—C31—C32	13.6 (4)
N2—N3—C11—C12	−0.1 (3)	C26—C27—C31—C32	−163.3 (2)
N2—N3—C11—C7	−178.5 (2)	N5—N4—C32—C31	−0.4 (2)
C8—C7—C11—N3	24.2 (3)	C33—N4—C32—C31	176.4 (2)
C6—C7—C11—N3	−155.8 (2)	N5—N4—C32—C12	178.81 (19)
C8—C7—C11—C12	−153.9 (2)	C33—N4—C32—C12	−4.4 (3)
C6—C7—C11—C12	26.2 (4)	N6—C31—C32—N4	0.4 (2)
N2—N1—C12—C11	0.3 (2)	C27—C31—C32—N4	178.1 (2)
C13—N1—C12—C11	−176.4 (2)	N6—C31—C32—C12	−178.6 (2)
N2—N1—C12—C32	−178.5 (2)	C27—C31—C32—C12	−0.9 (4)
C13—N1—C12—C32	4.8 (3)	N1—C12—C32—N4	−96.3 (3)
N3—C11—C12—N1	−0.2 (2)	C11—C12—C32—N4	85.2 (3)
C7—C11—C12—N1	178.1 (2)	N1—C12—C32—C31	82.6 (3)
N3—C11—C12—C32	178.5 (2)	C11—C12—C32—C31	−95.9 (3)
C7—C11—C12—C32	−3.3 (4)	N5—N4—C33—C34	86.5 (2)
N2—N1—C13—C14	102.5 (2)	C32—N4—C33—C34	−90.0 (3)
C12—N1—C13—C14	−81.1 (3)	N4—C33—C34—C39	−25.5 (3)
N1—C13—C14—C15	125.2 (2)	N4—C33—C34—C35	154.5 (2)
N1—C13—C14—C19	−56.2 (3)	C39—C34—C35—C36	0.8 (5)
C19—C14—C15—C16	1.0 (4)	C33—C34—C35—C36	−179.2 (3)
C13—C14—C15—C16	179.5 (2)	C34—C35—C36—C37	−0.8 (6)
C14—C15—C16—C17	0.2 (4)	C35—C36—C37—C38	0.2 (7)
C15—C16—C17—C18	−1.3 (5)	C36—C37—C38—C39	0.4 (6)
C16—C17—C18—C19	1.2 (5)	C35—C34—C39—C38	−0.2 (4)
C15—C14—C19—C18	−1.1 (4)	C33—C34—C39—C38	179.8 (3)
C13—C14—C19—C18	−179.6 (2)	C37—C38—C39—C34	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.45	3.292 (3)	148.
C33—H33B···O2ii	0.99	2.33	3.307 (3)	168.
C10—H10C···O4iii	0.98	2.52	3.337 (4)	141.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.45	3.292 (3)	148
C33—H33B⋯O2ii	0.99	2.33	3.307 (3)	168
C10—H10C⋯O4iii	0.98	2.52	3.337 (4)	141

Symmetry codes: (i) ; (ii) ; (iii) .