1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-methyl-2',3',5',6',7',7a'-octa-hydro-1'H-dispiro-[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione.

In the title compound C38H32N4O3, one pyrrolidine ring adopts an envelope conformation with the N atom as the flap while other pyrrolidine ring adopts an twisted conformation. The pyrrolizine ring forms dihedral angles of 79.24 (5) and 77.57 (5)° with the chromene and indole rings, respectively. The carbonyl O atoms deviate from the least-square planes through the chromene and indole rings by 0.0113 (12) and 0.0247 (12) Å, respectively. In the crystal, non-classical C-H⋯O inter-actions link the mol-ecules, generating an C(9) chain along the b-axis direction.

Related literature

For the biological activity of pyrazole derivatives, see: Mahajan et al. (1991 ▶); Baraldi et al. (1998 ▶); Katayama & Oshiyama (1997 ▶); Chen & Li (1998 ▶). For a related structure, see: Fun et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C38H32N4O3

M = 592.68

Triclinic,

a = 10.8240 (3) Å

b = 10.8382 (3) Å

c = 13.9127 (4) Å

α = 70.290 (1)°

β = 88.946 (2)°

γ = 73.578 (1)°

V = 1468.47 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.975, T max = 0.983

35301 measured reflections

9340 independent reflections

5865 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.166

S = 1.06

9340 reflections

406 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002043/rk2391sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002043/rk2391Isup2.hkl

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

C38H32N4O3	Z = 2
Mr = 592.68	F(000) = 624
Triclinic, P1	Dx = 1.340 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8240 (3) Å	Cell parameters from 9340 reflections
b = 10.8382 (3) Å	θ = 2.1–31.2°
c = 13.9127 (4) Å	µ = 0.09 mm−1
α = 70.290 (1)°	T = 295 K
β = 88.946 (2)°	Block, colourless
γ = 73.578 (1)°	0.30 × 0.25 × 0.20 mm
V = 1468.47 (7) Å3

Bruker Kappa APEXII CCD diffractometer	9340 independent reflections
Radiation source: fine-focus sealed tube	5865 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 31.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.975, Tmax = 0.983	k = −15→15
35301 measured reflections	l = −20→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0793P)2 + 0.1729P] where P = (Fo2 + 2Fc2)/3
9340 reflections	(Δ/σ)max < 0.001
406 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	1.20015 (16)	0.45544 (16)	0.12448 (12)	0.0447 (4)
H1	1.1229	0.5038	0.1421	0.054*
C2	1.3123 (2)	0.4889 (2)	0.13459 (15)	0.0582 (5)
H2	1.3102	0.5594	0.1589	0.070*
C3	1.4264 (2)	0.4182 (2)	0.10881 (18)	0.0723 (6)
H3	1.5022	0.4389	0.1174	0.087*
C4	1.42844 (19)	0.3164 (2)	0.07008 (19)	0.0758 (6)
H4	1.5054	0.2702	0.0507	0.091*
C5	1.31727 (17)	0.28249 (19)	0.05992 (15)	0.0543 (4)
H5	1.3197	0.2134	0.0338	0.065*
C6	1.20183 (14)	0.35058 (14)	0.08829 (11)	0.0365 (3)
C7	1.08498 (13)	0.30861 (14)	0.08134 (11)	0.0335 (3)
C8	0.90446 (14)	0.17479 (14)	−0.03996 (11)	0.0372 (3)
C9	0.94126 (19)	0.19600 (19)	−0.13752 (13)	0.0521 (4)
H9	1.0018	0.2431	−0.1609	0.063*
C10	0.8874 (2)	0.1466 (2)	−0.20098 (16)	0.0649 (5)
H10	0.9118	0.1614	−0.2674	0.078*
C11	0.7992 (2)	0.0766 (2)	−0.16741 (17)	0.0626 (5)
H11	0.7643	0.0429	−0.2103	0.075*
C12	0.76284 (19)	0.05675 (19)	−0.07089 (16)	0.0587 (5)
H12	0.7018	0.0101	−0.0482	0.070*
C13	0.81477 (17)	0.10454 (17)	−0.00578 (14)	0.0489 (4)
H13	0.7896	0.0896	0.0605	0.059*
C14	0.91574 (14)	0.23330 (15)	0.11587 (11)	0.0380 (3)
H14	0.8460	0.2064	0.1464	0.046*
C15	0.99309 (13)	0.28870 (14)	0.15423 (11)	0.0338 (3)
C16	0.98987 (13)	0.30356 (13)	0.25733 (10)	0.0319 (3)
H16	1.0618	0.3383	0.2658	0.038*
C17	1.01160 (14)	0.16187 (14)	0.34315 (11)	0.0374 (3)
H17	0.9760	0.1025	0.3194	0.045*
C18	1.15159 (16)	0.08961 (18)	0.38548 (13)	0.0510 (4)
H18A	1.1669	−0.0088	0.4150	0.061*
H18B	1.2098	0.1090	0.3323	0.061*
C19	1.16913 (18)	0.1481 (2)	0.46624 (16)	0.0677 (6)
H19A	1.2281	0.0789	0.5229	0.081*
H19B	1.2041	0.2248	0.4380	0.081*
C20	1.03935 (16)	0.1942 (2)	0.50153 (13)	0.0508 (4)
H20A	1.0344	0.1345	0.5705	0.061*
H20B	1.0223	0.2870	0.5015	0.061*
C21	0.82823 (13)	0.30387 (14)	0.38591 (10)	0.0322 (3)
C22	0.76483 (14)	0.36324 (14)	0.46523 (11)	0.0347 (3)
C23	0.79918 (15)	0.43927 (16)	0.51647 (11)	0.0407 (3)
H23	0.8702	0.4719	0.4990	0.049*
C24	0.72698 (17)	0.46666 (18)	0.59423 (12)	0.0474 (4)
H24	0.7498	0.5180	0.6288	0.057*
C25	0.62210 (17)	0.41859 (19)	0.62049 (13)	0.0529 (4)
H25	0.5754	0.4368	0.6734	0.063*
C26	0.58482 (16)	0.34373 (19)	0.56975 (13)	0.0502 (4)
H26	0.5133	0.3119	0.5873	0.060*
C28	0.53123 (18)	0.1847 (2)	0.43800 (18)	0.0645 (5)
H27A	0.4777	0.2036	0.4901	0.097*
H27B	0.5660	0.0874	0.4550	0.097*
H27C	0.4805	0.2233	0.3733	0.097*
C29	0.72848 (14)	0.23509 (14)	0.36510 (11)	0.0368 (3)
C30	0.86386 (13)	0.39982 (13)	0.28047 (10)	0.0294 (3)
C31	0.89175 (14)	0.52146 (14)	0.29848 (10)	0.0341 (3)
C32	0.78405 (15)	0.64959 (14)	0.27149 (11)	0.0378 (3)
C33	0.7986 (2)	0.76442 (17)	0.28913 (14)	0.0514 (4)
H32	0.8775	0.7606	0.3172	0.062*
C34	0.6973 (2)	0.88303 (19)	0.26547 (16)	0.0662 (6)
H33	0.7080	0.9590	0.2773	0.079*
C35	0.5800 (2)	0.88894 (19)	0.22412 (17)	0.0663 (5)
H34	0.5120	0.9694	0.2080	0.080*
C36	0.56248 (19)	0.77743 (18)	0.20650 (15)	0.0551 (4)
H35	0.4831	0.7819	0.1789	0.066*
C37	0.66482 (15)	0.65802 (15)	0.23050 (12)	0.0396 (3)
C38	0.75803 (14)	0.45991 (14)	0.19302 (11)	0.0352 (3)
H37A	0.7906	0.5106	0.1314	0.042*
H37B	0.7363	0.3856	0.1802	0.042*
N1	0.94466 (12)	0.18845 (12)	0.42931 (9)	0.0362 (3)
C27	0.65651 (14)	0.31774 (15)	0.49263 (11)	0.0384 (3)
N3	0.63590 (12)	0.24491 (13)	0.43134 (10)	0.0424 (3)
N4	0.95794 (12)	0.22443 (12)	0.02610 (9)	0.0359 (3)
N5	1.06305 (12)	0.27041 (12)	0.00305 (9)	0.0372 (3)
O1	0.64346 (10)	0.54909 (10)	0.21348 (8)	0.0419 (3)
O2	0.99610 (11)	0.51308 (12)	0.33489 (9)	0.0505 (3)
O3	0.73360 (11)	0.17644 (12)	0.30382 (9)	0.0491 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0454 (9)	0.0474 (8)	0.0443 (9)	−0.0211 (7)	0.0063 (7)	−0.0136 (7)
C2	0.0624 (12)	0.0633 (11)	0.0570 (11)	−0.0352 (9)	0.0015 (9)	−0.0170 (9)
C3	0.0483 (11)	0.0859 (15)	0.0876 (16)	−0.0369 (11)	−0.0011 (10)	−0.0214 (12)
C4	0.0356 (10)	0.0840 (15)	0.1056 (18)	−0.0183 (10)	0.0170 (10)	−0.0299 (13)
C5	0.0407 (9)	0.0576 (10)	0.0662 (12)	−0.0152 (8)	0.0131 (8)	−0.0233 (9)
C6	0.0354 (7)	0.0395 (7)	0.0319 (7)	−0.0149 (6)	0.0040 (6)	−0.0059 (6)
C7	0.0336 (7)	0.0340 (6)	0.0315 (7)	−0.0102 (5)	0.0043 (5)	−0.0094 (5)
C8	0.0376 (8)	0.0343 (7)	0.0388 (8)	−0.0065 (6)	−0.0005 (6)	−0.0147 (6)
C9	0.0602 (11)	0.0633 (10)	0.0443 (9)	−0.0247 (9)	0.0102 (8)	−0.0278 (8)
C10	0.0746 (14)	0.0794 (13)	0.0519 (11)	−0.0200 (11)	0.0041 (10)	−0.0388 (10)
C11	0.0603 (12)	0.0649 (11)	0.0723 (13)	−0.0111 (9)	−0.0119 (10)	−0.0410 (10)
C12	0.0560 (11)	0.0580 (10)	0.0727 (13)	−0.0235 (9)	−0.0015 (9)	−0.0300 (10)
C13	0.0513 (10)	0.0517 (9)	0.0503 (10)	−0.0212 (8)	0.0037 (8)	−0.0209 (8)
C14	0.0378 (8)	0.0451 (8)	0.0369 (8)	−0.0175 (6)	0.0097 (6)	−0.0175 (6)
C15	0.0335 (7)	0.0363 (7)	0.0324 (7)	−0.0112 (5)	0.0047 (5)	−0.0121 (5)
C16	0.0298 (7)	0.0378 (7)	0.0308 (7)	−0.0131 (5)	0.0043 (5)	−0.0125 (5)
C17	0.0396 (8)	0.0373 (7)	0.0332 (7)	−0.0105 (6)	0.0049 (6)	−0.0102 (6)
C18	0.0431 (9)	0.0510 (9)	0.0440 (9)	0.0003 (7)	0.0036 (7)	−0.0093 (7)
C19	0.0425 (10)	0.0907 (15)	0.0651 (13)	−0.0051 (10)	−0.0079 (9)	−0.0323 (11)
C20	0.0420 (9)	0.0666 (10)	0.0425 (9)	−0.0129 (8)	−0.0028 (7)	−0.0194 (8)
C21	0.0319 (7)	0.0362 (6)	0.0319 (7)	−0.0157 (5)	0.0054 (5)	−0.0115 (5)
C22	0.0335 (7)	0.0408 (7)	0.0304 (7)	−0.0140 (6)	0.0072 (5)	−0.0109 (6)
C23	0.0402 (8)	0.0508 (8)	0.0359 (8)	−0.0182 (7)	0.0062 (6)	−0.0172 (7)
C24	0.0468 (9)	0.0586 (9)	0.0398 (8)	−0.0131 (7)	0.0049 (7)	−0.0229 (7)
C25	0.0457 (9)	0.0708 (11)	0.0418 (9)	−0.0125 (8)	0.0141 (7)	−0.0235 (8)
C26	0.0375 (8)	0.0648 (10)	0.0470 (9)	−0.0184 (7)	0.0146 (7)	−0.0156 (8)
C28	0.0468 (10)	0.0686 (12)	0.0983 (16)	−0.0378 (9)	0.0225 (10)	−0.0377 (11)
C29	0.0372 (8)	0.0363 (7)	0.0389 (8)	−0.0172 (6)	0.0054 (6)	−0.0102 (6)
C30	0.0294 (6)	0.0337 (6)	0.0285 (6)	−0.0139 (5)	0.0031 (5)	−0.0110 (5)
C31	0.0369 (7)	0.0426 (7)	0.0304 (7)	−0.0215 (6)	0.0078 (6)	−0.0140 (6)
C32	0.0470 (9)	0.0370 (7)	0.0350 (7)	−0.0196 (6)	0.0121 (6)	−0.0140 (6)
C33	0.0688 (12)	0.0483 (9)	0.0525 (10)	−0.0307 (8)	0.0178 (9)	−0.0259 (8)
C34	0.0953 (17)	0.0428 (9)	0.0710 (13)	−0.0274 (10)	0.0283 (12)	−0.0281 (9)
C35	0.0771 (15)	0.0425 (9)	0.0727 (13)	−0.0060 (9)	0.0175 (11)	−0.0218 (9)
C36	0.0497 (10)	0.0483 (9)	0.0594 (11)	−0.0049 (7)	0.0085 (8)	−0.0166 (8)
C37	0.0438 (8)	0.0382 (7)	0.0377 (8)	−0.0134 (6)	0.0097 (6)	−0.0134 (6)
C38	0.0348 (7)	0.0377 (7)	0.0344 (7)	−0.0112 (6)	0.0011 (6)	−0.0135 (6)
N1	0.0357 (6)	0.0400 (6)	0.0302 (6)	−0.0121 (5)	0.0037 (5)	−0.0081 (5)
C27	0.0336 (7)	0.0423 (7)	0.0378 (8)	−0.0137 (6)	0.0059 (6)	−0.0102 (6)
N3	0.0360 (7)	0.0476 (7)	0.0512 (8)	−0.0237 (6)	0.0116 (6)	−0.0176 (6)
N4	0.0362 (6)	0.0417 (6)	0.0339 (6)	−0.0146 (5)	0.0054 (5)	−0.0159 (5)
N5	0.0361 (6)	0.0444 (6)	0.0343 (6)	−0.0156 (5)	0.0079 (5)	−0.0150 (5)
O1	0.0319 (5)	0.0426 (5)	0.0525 (6)	−0.0097 (4)	0.0006 (5)	−0.0188 (5)
O2	0.0417 (6)	0.0613 (7)	0.0626 (8)	−0.0254 (5)	0.0011 (5)	−0.0304 (6)
O3	0.0546 (7)	0.0542 (6)	0.0554 (7)	−0.0307 (6)	0.0112 (6)	−0.0284 (6)

C1—C2	1.383 (2)	C20—H20A	0.9700
C1—C6	1.385 (2)	C20—H20B	0.9700
C1—H1	0.9300	C21—N1	1.4645 (18)
C2—C3	1.369 (3)	C21—C22	1.518 (2)
C2—H2	0.9300	C21—C29	1.5548 (19)
C3—C4	1.377 (3)	C21—C30	1.5998 (18)
C3—H3	0.9300	C22—C23	1.380 (2)
C4—C5	1.376 (3)	C22—C27	1.395 (2)
C4—H4	0.9300	C23—C24	1.387 (2)
C5—C6	1.385 (2)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.373 (2)
C6—C7	1.475 (2)	C24—H24	0.9300
C7—N5	1.3354 (18)	C25—C26	1.379 (3)
C7—C15	1.4146 (19)	C25—H25	0.9300
C8—C9	1.369 (2)	C26—C27	1.372 (2)
C8—C13	1.380 (2)	C26—H26	0.9300
C8—N4	1.4137 (18)	C28—N3	1.446 (2)
C9—C10	1.385 (2)	C28—H27A	0.9600
C9—H9	0.9300	C28—H27B	0.9600
C10—C11	1.364 (3)	C28—H27C	0.9600
C10—H10	0.9300	C29—O3	1.2157 (18)
C11—C12	1.356 (3)	C29—N3	1.3553 (19)
C11—H11	0.9300	C30—C38	1.5204 (19)
C12—C13	1.380 (2)	C30—C31	1.5305 (18)
C12—H12	0.9300	C31—O2	1.2136 (17)
C13—H13	0.9300	C31—C32	1.476 (2)
C14—N4	1.3465 (18)	C32—C37	1.387 (2)
C14—C15	1.365 (2)	C32—C33	1.397 (2)
C14—H14	0.9300	C33—C34	1.376 (3)
C15—C16	1.4952 (19)	C33—H32	0.9300
C16—C17	1.5519 (19)	C34—C35	1.380 (3)
C16—C30	1.5678 (18)	C34—H33	0.9300
C16—H16	0.9800	C35—C36	1.374 (3)
C17—N1	1.4587 (19)	C35—H34	0.9300
C17—C18	1.519 (2)	C36—C37	1.387 (2)
C17—H17	0.9800	C36—H35	0.9300
C18—C19	1.502 (3)	C37—O1	1.3595 (17)
C18—H18A	0.9700	C38—O1	1.4311 (17)
C18—H18B	0.9700	C38—H37A	0.9700
C19—C20	1.486 (3)	C38—H37B	0.9700
C19—H19A	0.9700	C27—N3	1.400 (2)
C19—H19B	0.9700	N4—N5	1.3582 (16)
C20—N1	1.476 (2)
C2—C1—C6	120.59 (17)	N1—C21—C29	103.59 (11)
C2—C1—H1	119.7	C22—C21—C29	101.45 (11)
C6—C1—H1	119.7	N1—C21—C30	106.50 (11)
C3—C2—C1	120.08 (18)	C22—C21—C30	121.01 (11)
C3—C2—H2	120.0	C29—C21—C30	110.50 (11)
C1—C2—H2	120.0	C23—C22—C27	118.57 (13)
C2—C3—C4	119.79 (18)	C23—C22—C21	133.02 (13)
C2—C3—H3	120.1	C27—C22—C21	108.19 (12)
C4—C3—H3	120.1	C22—C23—C24	119.54 (14)
C5—C4—C3	120.40 (19)	C22—C23—H23	120.2
C5—C4—H4	119.8	C24—C23—H23	120.2
C3—C4—H4	119.8	C25—C24—C23	120.49 (16)
C4—C5—C6	120.44 (18)	C25—C24—H24	119.8
C4—C5—H5	119.8	C23—C24—H24	119.8
C6—C5—H5	119.8	C24—C25—C26	121.14 (15)
C5—C6—C1	118.64 (14)	C24—C25—H25	119.4
C5—C6—C7	119.68 (14)	C26—C25—H25	119.4
C1—C6—C7	121.67 (14)	C27—C26—C25	117.91 (15)
N5—C7—C15	111.59 (12)	C27—C26—H26	121.0
N5—C7—C6	119.80 (13)	C25—C26—H26	121.0
C15—C7—C6	128.29 (13)	N3—C28—H27A	109.5
C9—C8—C13	119.92 (15)	N3—C28—H27B	109.5
C9—C8—N4	120.33 (14)	H27A—C28—H27B	109.5
C13—C8—N4	119.74 (14)	N3—C28—H27C	109.5
C8—C9—C10	119.34 (18)	H27A—C28—H27C	109.5
C8—C9—H9	120.3	H27B—C28—H27C	109.5
C10—C9—H9	120.3	O3—C29—N3	124.73 (14)
C11—C10—C9	120.95 (19)	O3—C29—C21	126.96 (13)
C11—C10—H10	119.5	N3—C29—C21	108.23 (12)
C9—C10—H10	119.5	C38—C30—C31	106.51 (11)
C12—C11—C10	119.30 (17)	C38—C30—C16	112.90 (11)
C12—C11—H11	120.4	C31—C30—C16	110.79 (11)
C10—C11—H11	120.4	C38—C30—C21	115.00 (11)
C11—C12—C13	121.15 (18)	C31—C30—C21	108.62 (10)
C11—C12—H12	119.4	C16—C30—C21	103.01 (10)
C13—C12—H12	119.4	O2—C31—C32	121.27 (13)
C12—C13—C8	119.34 (17)	O2—C31—C30	122.10 (13)
C12—C13—H13	120.3	C32—C31—C30	116.62 (12)
C8—C13—H13	120.3	C37—C32—C33	118.30 (15)
N4—C14—C15	108.14 (13)	C37—C32—C31	120.90 (13)
N4—C14—H14	125.9	C33—C32—C31	120.78 (15)
C15—C14—H14	125.9	C34—C33—C32	120.66 (19)
C14—C15—C7	104.05 (12)	C34—C33—H32	119.7
C14—C15—C16	126.24 (13)	C32—C33—H32	119.7
C7—C15—C16	129.14 (13)	C33—C34—C35	119.85 (17)
C15—C16—C17	110.44 (11)	C33—C34—H33	120.1
C15—C16—C30	117.73 (11)	C35—C34—H33	120.1
C17—C16—C30	105.55 (10)	C36—C35—C34	120.85 (18)
C15—C16—H16	107.6	C36—C35—H34	119.6
C17—C16—H16	107.6	C34—C35—H34	119.6
C30—C16—H16	107.6	C35—C36—C37	119.11 (19)
N1—C17—C18	104.84 (12)	C35—C36—H35	120.4
N1—C17—C16	106.34 (11)	C37—C36—H35	120.4
C18—C17—C16	114.24 (13)	O1—C37—C32	121.25 (13)
N1—C17—H17	110.4	O1—C37—C36	117.52 (15)
C18—C17—H17	110.4	C32—C37—C36	121.23 (15)
C16—C17—H17	110.4	O1—C38—C30	113.00 (11)
C19—C18—C17	103.82 (13)	O1—C38—H37A	109.0
C19—C18—H18A	111.0	C30—C38—H37A	109.0
C17—C18—H18A	111.0	O1—C38—H37B	109.0
C19—C18—H18B	111.0	C30—C38—H37B	109.0
C17—C18—H18B	111.0	H37A—C38—H37B	107.8
H18A—C18—H18B	109.0	C17—N1—C21	106.82 (11)
C20—C19—C18	106.76 (15)	C17—N1—C20	108.47 (12)
C20—C19—H19A	110.4	C21—N1—C20	120.70 (12)
C18—C19—H19A	110.4	C26—C27—C22	122.34 (15)
C20—C19—H19B	110.4	C26—C27—N3	127.43 (14)
C18—C19—H19B	110.4	C22—C27—N3	110.23 (13)
H19A—C19—H19B	108.6	C29—N3—C27	111.44 (12)
N1—C20—C19	106.76 (14)	C29—N3—C28	123.50 (14)
N1—C20—H20A	110.4	C27—N3—C28	125.06 (14)
C19—C20—H20A	110.4	C14—N4—N5	111.74 (11)
N1—C20—H20B	110.4	C14—N4—C8	126.92 (12)
C19—C20—H20B	110.4	N5—N4—C8	121.34 (12)
H20A—C20—H20B	108.6	C7—N5—N4	104.48 (11)
N1—C21—C22	112.43 (11)	C37—O1—C38	112.91 (11)
C6—C1—C2—C3	0.0 (3)	N1—C21—C30—C16	16.80 (13)
C1—C2—C3—C4	1.8 (3)	C22—C21—C30—C16	146.76 (12)
C2—C3—C4—C5	−1.9 (4)	C29—C21—C30—C16	−95.07 (12)
C3—C4—C5—C6	0.2 (3)	C38—C30—C31—O2	−153.47 (14)
C4—C5—C6—C1	1.6 (3)	C16—C30—C31—O2	−30.33 (18)
C4—C5—C6—C7	−177.19 (17)	C21—C30—C31—O2	82.13 (16)
C2—C1—C6—C5	−1.7 (2)	C38—C30—C31—C32	27.90 (16)
C2—C1—C6—C7	177.10 (15)	C16—C30—C31—C32	151.04 (12)
C5—C6—C7—N5	−37.9 (2)	C21—C30—C31—C32	−96.50 (13)
C1—C6—C7—N5	143.31 (14)	O2—C31—C32—C37	−179.59 (14)
C5—C6—C7—C15	134.98 (17)	C30—C31—C32—C37	−0.94 (19)
C1—C6—C7—C15	−43.8 (2)	O2—C31—C32—C33	−1.3 (2)
C13—C8—C9—C10	0.1 (3)	C30—C31—C32—C33	177.34 (13)
N4—C8—C9—C10	−179.90 (16)	C37—C32—C33—C34	−0.6 (2)
C8—C9—C10—C11	−0.4 (3)	C31—C32—C33—C34	−178.92 (16)
C9—C10—C11—C12	0.8 (3)	C32—C33—C34—C35	0.2 (3)
C10—C11—C12—C13	−0.8 (3)	C33—C34—C35—C36	0.3 (3)
C11—C12—C13—C8	0.5 (3)	C34—C35—C36—C37	−0.3 (3)
C9—C8—C13—C12	−0.2 (2)	C33—C32—C37—O1	−178.60 (13)
N4—C8—C13—C12	179.84 (15)	C31—C32—C37—O1	−0.3 (2)
N4—C14—C15—C7	−1.22 (15)	C33—C32—C37—C36	0.6 (2)
N4—C14—C15—C16	−173.21 (13)	C31—C32—C37—C36	178.93 (14)
N5—C7—C15—C14	1.20 (16)	C35—C36—C37—O1	179.05 (16)
C6—C7—C15—C14	−172.17 (14)	C35—C36—C37—C32	−0.2 (3)
N5—C7—C15—C16	172.87 (13)	C31—C30—C38—O1	−57.50 (14)
C6—C7—C15—C16	−0.5 (2)	C16—C30—C38—O1	−179.31 (10)
C14—C15—C16—C17	57.39 (18)	C21—C30—C38—O1	62.87 (15)
C7—C15—C16—C17	−112.57 (15)	C18—C17—N1—C21	156.51 (12)
C14—C15—C16—C30	−63.88 (18)	C16—C17—N1—C21	35.16 (14)
C7—C15—C16—C30	126.16 (15)	C18—C17—N1—C20	24.96 (16)
C15—C16—C17—N1	−151.63 (12)	C16—C17—N1—C20	−96.39 (14)
C30—C16—C17—N1	−23.37 (14)	C22—C21—N1—C17	−167.23 (11)
C15—C16—C17—C18	93.24 (15)	C29—C21—N1—C17	84.06 (13)
C30—C16—C17—C18	−138.51 (13)	C30—C21—N1—C17	−32.52 (13)
N1—C17—C18—C19	−30.83 (17)	C22—C21—N1—C20	−42.87 (17)
C16—C17—C18—C19	85.18 (17)	C29—C21—N1—C20	−151.58 (13)
C17—C18—C19—C20	25.5 (2)	C30—C21—N1—C20	91.84 (14)
C18—C19—C20—N1	−10.8 (2)	C19—C20—N1—C17	−9.05 (19)
N1—C21—C22—C23	71.02 (19)	C19—C20—N1—C21	−132.63 (16)
C29—C21—C22—C23	−178.92 (15)	C25—C26—C27—C22	0.5 (2)
C30—C21—C22—C23	−56.3 (2)	C25—C26—C27—N3	−179.74 (15)
N1—C21—C22—C27	−103.33 (14)	C23—C22—C27—C26	−1.3 (2)
C29—C21—C22—C27	6.73 (14)	C21—C22—C27—C26	174.04 (14)
C30—C21—C22—C27	129.33 (13)	C23—C22—C27—N3	178.97 (13)
C27—C22—C23—C24	0.9 (2)	C21—C22—C27—N3	−5.73 (16)
C21—C22—C23—C24	−172.97 (15)	O3—C29—N3—C27	179.58 (14)
C22—C23—C24—C25	0.1 (2)	C21—C29—N3—C27	2.63 (16)
C23—C24—C25—C26	−0.8 (3)	O3—C29—N3—C28	0.7 (3)
C24—C25—C26—C27	0.5 (3)	C21—C29—N3—C28	−176.27 (15)
N1—C21—C29—O3	−65.80 (18)	C26—C27—N3—C29	−177.82 (16)
C22—C21—C29—O3	177.48 (15)	C22—C27—N3—C29	1.94 (18)
C30—C21—C29—O3	47.92 (19)	C26—C27—N3—C28	1.1 (3)
N1—C21—C29—N3	111.05 (13)	C22—C27—N3—C28	−179.19 (16)
C22—C21—C29—N3	−5.66 (14)	C15—C14—N4—N5	0.90 (16)
C30—C21—C29—N3	−135.22 (12)	C15—C14—N4—C8	−179.04 (13)
C15—C16—C30—C38	2.92 (16)	C9—C8—N4—C14	167.31 (15)
C17—C16—C30—C38	−120.84 (12)	C13—C8—N4—C14	−12.7 (2)
C15—C16—C30—C31	−116.44 (13)	C9—C8—N4—N5	−12.6 (2)
C17—C16—C30—C31	119.80 (12)	C13—C8—N4—N5	167.32 (13)
C15—C16—C30—C21	127.57 (12)	C15—C7—N5—N4	−0.67 (15)
C17—C16—C30—C21	3.80 (13)	C6—C7—N5—N4	173.33 (12)
N1—C21—C30—C38	140.06 (11)	C14—N4—N5—C7	−0.13 (15)
C22—C21—C30—C38	−89.97 (15)	C8—N4—N5—C7	179.82 (12)
C29—C21—C30—C38	28.19 (16)	C32—C37—O1—C38	−28.68 (19)
N1—C21—C30—C31	−100.74 (12)	C36—C37—O1—C38	152.08 (14)
C22—C21—C30—C31	29.23 (16)	C30—C38—O1—C37	59.83 (15)
C29—C21—C30—C31	147.40 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C34—H33···O3i	0.93	2.59	3.523 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C34—H33⋯O3i	0.93	2.59	3.523 (3)	178

Symmetry code: (i) .