5′′-Benzyl­idene-1′-methyl-4′-phenyl­indole-3-spiro-2′-pyrrolidine-3′-spiro-3′′-piperidine-2(3H),4′′-dione

In the title compound, C₃₀H₂₉N₃O₂, the dihedral angle between the rings in the indole moiety is 3.3 (1)°. The piperidinone ring adopts a half-chair conformation. The dihedral angle between the pyrrolidine ring and the ox­indole moiety is 77.2 (1)°. The packing is stabilized by an N—H...O hydrogen bond and intermolecular C—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.148
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.97

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5''-Benzylidene-1'-methyl-4'-phenylindole-3-spiro-2'-pyrrolidine-3'-spiro-3''- piperidine-2(3H),4''-dione

Crystal data

C30H29N3O2	F(000) = 984
Mr = 463.56	Dx = 1.222 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.6889 (7) Å	Cell parameters from 2146 reflections
b = 18.9025 (12) Å	θ = 2.4–20.4°
c = 12.5270 (8) Å	µ = 0.08 mm^−1
β = 95.283 (1)°	T = 293 K
V = 2520.3 (3) Å^3	Block, colourless
Z = 4	0.21 × 0.20 × 0.20 mm

Data collection

CCD Area Detector diffractometer	3798 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.0°, θmin = 2.0°
ω scans	h = −14→13
15727 measured reflections	k = −21→24
5738 independent reflections	l = −13→16

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0826P)^2] where P = (Fo^2 + 2Fc^2)/3
5738 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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
N1	0.48578 (12)	0.05034 (8)	0.13101 (11)	0.0415 (4)
H1	0.4284	0.0308	0.0882	0.050*
C2	0.46189 (15)	0.09039 (9)	0.22118 (13)	0.0380 (4)
C3	0.34809 (16)	0.10568 (10)	0.25845 (15)	0.0489 (5)
H3	0.2729	0.0920	0.2209	0.059*
C4	0.35009 (19)	0.14222 (12)	0.35403 (17)	0.0609 (6)
H4	0.2744	0.1538	0.3807	0.073*
C5	0.46088 (19)	0.16194 (12)	0.41093 (17)	0.0588 (5)
H5	0.4592	0.1860	0.4756	0.071*
C6	0.57489 (17)	0.14610 (10)	0.37227 (14)	0.0468 (4)
H6	0.6500	0.1587	0.4110	0.056*
C7	0.57542 (15)	0.11133 (9)	0.27529 (13)	0.0364 (4)
C8	0.68287 (14)	0.08674 (9)	0.21422 (13)	0.0364 (4)
C9	0.61006 (15)	0.04616 (9)	0.11963 (13)	0.0394 (4)
N10	0.76906 (13)	0.04031 (8)	0.27999 (11)	0.0429 (4)
C11	0.88892 (15)	0.04145 (10)	0.23388 (15)	0.0468 (5)
H11A	0.8848	0.0156	0.1667	0.056*
H11B	0.9556	0.0219	0.2829	0.056*
C12	0.90743 (14)	0.11982 (9)	0.21664 (13)	0.0387 (4)
H12	0.9259	0.1410	0.2877	0.046*
C13	0.77340 (14)	0.14584 (9)	0.17336 (13)	0.0348 (4)
C14	1.01211 (15)	0.14221 (10)	0.15007 (14)	0.0408 (4)
C15	1.06749 (17)	0.20810 (10)	0.16772 (16)	0.0511 (5)
H15	1.0402	0.2373	0.2207	0.061*
C16	1.1621 (2)	0.23136 (12)	0.10851 (18)	0.0613 (6)
H16	1.1973	0.2759	0.1214	0.074*
C17	1.2040 (2)	0.18905 (14)	0.03097 (18)	0.0648 (6)
H17	1.2679	0.2046	−0.0089	0.078*
C18	1.15167 (18)	0.12389 (13)	0.01214 (16)	0.0622 (6)
H18	1.1801	0.0950	−0.0406	0.075*
C19	1.05615 (17)	0.10046 (11)	0.07138 (15)	0.0525 (5)
H19	1.0213	0.0559	0.0578	0.063*
C20	0.75705 (14)	0.15373 (9)	0.05112 (13)	0.0395 (4)
H20A	0.8101	0.1916	0.0289	0.047*
H20B	0.7810	0.1102	0.0173	0.047*
N21	0.62564 (12)	0.16966 (8)	0.01937 (10)	0.0394 (3)
C22	0.59718 (17)	0.24224 (9)	0.04656 (14)	0.0430 (4)
H22A	0.5074	0.2501	0.0329	0.052*
H22B	0.6393	0.2740	0.0007	0.052*
C23	0.63742 (15)	0.25949 (9)	0.16199 (13)	0.0377 (4)
C24	0.74271 (15)	0.21831 (9)	0.21959 (13)	0.0370 (4)
C25	0.58269 (16)	0.30882 (9)	0.21864 (14)	0.0422 (4)
H25	0.6146	0.3130	0.2900	0.051*
C26	0.47978 (16)	0.35719 (9)	0.18434 (14)	0.0419 (4)
C27	0.4547 (2)	0.38209 (10)	0.08044 (16)	0.0568 (5)
H27	0.5054	0.3678	0.0279	0.068*
C28	0.3560 (2)	0.42775 (12)	0.05358 (19)	0.0702 (7)
H28	0.3397	0.4431	−0.0169	0.084*
C29	0.2820 (2)	0.45048 (12)	0.1303 (2)	0.0746 (7)
H29	0.2148	0.4807	0.1119	0.089*
C30	0.3074 (2)	0.42850 (12)	0.2343 (2)	0.0700 (6)
H30	0.2588	0.4449	0.2870	0.084*
C31	0.40445 (19)	0.38222 (11)	0.26091 (17)	0.0561 (5)
H31	0.4201	0.3673	0.3316	0.067*
O32	0.65823 (11)	0.01101 (7)	0.05185 (10)	0.0491 (3)
C33	0.71957 (19)	−0.02955 (11)	0.30353 (18)	0.0598 (5)
H33A	0.6405	−0.0243	0.3334	0.090*
H33B	0.7779	−0.0535	0.3540	0.090*
H33C	0.7078	−0.0567	0.2386	0.090*
C34	0.58851 (19)	0.15563 (11)	−0.09321 (15)	0.0557 (5)
H34A	0.6088	0.1076	−0.1096	0.084*
H34B	0.6326	0.1872	−0.1367	0.084*
H34C	0.4997	0.1628	−0.1076	0.084*
O35	0.80183 (11)	0.24174 (7)	0.29905 (10)	0.0513 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0339 (7)	0.0455 (9)	0.0435 (8)	−0.0055 (6)	−0.0051 (6)	−0.0087 (6)
C2	0.0374 (9)	0.0363 (9)	0.0396 (9)	−0.0018 (7)	−0.0006 (7)	−0.0006 (7)
C3	0.0352 (9)	0.0580 (12)	0.0529 (12)	−0.0006 (8)	0.0020 (8)	0.0008 (9)
C4	0.0475 (11)	0.0761 (15)	0.0611 (14)	0.0052 (10)	0.0158 (10)	−0.0062 (11)
C5	0.0589 (12)	0.0695 (14)	0.0494 (12)	0.0011 (10)	0.0118 (10)	−0.0147 (10)
C6	0.0441 (10)	0.0542 (12)	0.0415 (10)	−0.0017 (8)	0.0012 (8)	−0.0078 (8)
C7	0.0359 (8)	0.0361 (9)	0.0369 (9)	0.0011 (7)	0.0017 (7)	−0.0010 (7)
C8	0.0339 (8)	0.0371 (9)	0.0369 (9)	0.0019 (7)	−0.0034 (7)	−0.0046 (7)
C9	0.0388 (9)	0.0359 (9)	0.0423 (10)	0.0004 (7)	−0.0036 (7)	−0.0050 (7)
N10	0.0373 (8)	0.0427 (8)	0.0473 (9)	0.0037 (6)	−0.0034 (6)	0.0033 (6)
C11	0.0367 (9)	0.0487 (11)	0.0530 (11)	0.0097 (8)	−0.0059 (8)	−0.0030 (8)
C12	0.0316 (8)	0.0455 (10)	0.0379 (9)	0.0038 (7)	−0.0035 (7)	−0.0072 (7)
C13	0.0285 (8)	0.0394 (9)	0.0358 (9)	0.0020 (6)	−0.0013 (7)	−0.0057 (7)
C14	0.0287 (8)	0.0516 (11)	0.0404 (10)	0.0046 (7)	−0.0055 (7)	−0.0063 (8)
C15	0.0428 (10)	0.0535 (12)	0.0558 (12)	0.0000 (9)	−0.0009 (9)	−0.0082 (9)
C16	0.0529 (12)	0.0614 (14)	0.0687 (15)	−0.0084 (10)	0.0012 (11)	0.0082 (11)
C17	0.0481 (12)	0.0900 (18)	0.0566 (13)	0.0012 (12)	0.0059 (10)	0.0177 (12)
C18	0.0501 (12)	0.0885 (17)	0.0485 (12)	0.0131 (11)	0.0079 (9)	−0.0079 (11)
C19	0.0446 (10)	0.0599 (13)	0.0521 (12)	0.0034 (9)	−0.0001 (9)	−0.0126 (9)
C20	0.0359 (9)	0.0438 (10)	0.0384 (10)	0.0035 (7)	0.0019 (7)	−0.0053 (7)
N21	0.0373 (7)	0.0440 (8)	0.0355 (8)	0.0049 (6)	−0.0041 (6)	−0.0056 (6)
C22	0.0405 (9)	0.0437 (10)	0.0439 (10)	0.0058 (8)	0.0001 (8)	0.0021 (8)
C23	0.0355 (9)	0.0358 (9)	0.0411 (10)	−0.0006 (7)	0.0003 (7)	−0.0015 (7)
C24	0.0343 (8)	0.0397 (9)	0.0370 (9)	−0.0023 (7)	0.0029 (7)	−0.0047 (7)
C25	0.0459 (10)	0.0397 (10)	0.0407 (10)	0.0013 (8)	0.0019 (8)	−0.0016 (7)
C26	0.0433 (9)	0.0354 (9)	0.0468 (11)	0.0023 (7)	0.0030 (8)	−0.0034 (7)
C27	0.0709 (13)	0.0492 (12)	0.0499 (12)	0.0147 (10)	0.0031 (10)	−0.0035 (9)
C28	0.0878 (17)	0.0568 (14)	0.0620 (14)	0.0223 (12)	−0.0141 (12)	−0.0028 (10)
C29	0.0609 (14)	0.0572 (14)	0.104 (2)	0.0205 (11)	−0.0031 (13)	0.0000 (13)
C30	0.0627 (14)	0.0599 (14)	0.0912 (18)	0.0163 (11)	0.0279 (13)	0.0057 (12)
C31	0.0625 (12)	0.0487 (12)	0.0595 (13)	0.0098 (10)	0.0177 (10)	0.0064 (9)
O32	0.0460 (7)	0.0500 (8)	0.0502 (8)	0.0043 (6)	−0.0023 (6)	−0.0203 (6)
C33	0.0576 (12)	0.0484 (12)	0.0720 (14)	0.0025 (9)	−0.0015 (10)	0.0122 (10)
C34	0.0598 (12)	0.0637 (13)	0.0411 (11)	0.0111 (10)	−0.0092 (9)	−0.0073 (9)
O35	0.0450 (7)	0.0541 (8)	0.0520 (8)	0.0059 (6)	−0.0097 (6)	−0.0190 (6)

Geometric parameters (Å, º)

N1—C9	1.351 (2)	C17—H17	0.9300
N1—C2	1.403 (2)	C18—C19	1.389 (3)
N1—H1	0.8600	C18—H18	0.9300
C2—C3	1.373 (2)	C19—H19	0.9300
C2—C7	1.392 (2)	C20—N21	1.4557 (19)
C3—C4	1.381 (3)	C20—H20A	0.9700
C3—H3	0.9300	C20—H20B	0.9700
C4—C5	1.376 (3)	N21—C22	1.453 (2)
C4—H4	0.9300	N21—C34	1.454 (2)
C5—C6	1.385 (3)	C22—C23	1.506 (2)
C5—H5	0.9300	C22—H22A	0.9700
C6—C7	1.382 (2)	C22—H22B	0.9700
C6—H6	0.9300	C23—C25	1.339 (2)
C7—C8	1.511 (2)	C23—C24	1.498 (2)
C8—N10	1.469 (2)	C24—O35	1.2126 (19)
C8—C9	1.558 (2)	C25—C26	1.464 (2)
C8—C13	1.593 (2)	C25—H25	0.9300
C9—O32	1.2280 (19)	C26—C27	1.387 (3)
N10—C11	1.453 (2)	C26—C31	1.391 (3)
N10—C33	1.463 (2)	C27—C28	1.381 (3)
C11—C12	1.513 (2)	C27—H27	0.9300
C11—H11A	0.9700	C28—C29	1.368 (3)
C11—H11B	0.9700	C28—H28	0.9300
C12—C14	1.516 (2)	C29—C30	1.371 (3)
C12—C13	1.564 (2)	C29—H29	0.9300
C12—H12	0.9800	C30—C31	1.374 (3)
C13—C20	1.532 (2)	C30—H30	0.9300
C13—C24	1.534 (2)	C31—H31	0.9300
C14—C19	1.379 (2)	C33—H33A	0.9600
C14—C15	1.388 (2)	C33—H33B	0.9600
C15—C16	1.380 (3)	C33—H33C	0.9600
C15—H15	0.9300	C34—H34A	0.9600
C16—C17	1.365 (3)	C34—H34B	0.9600
C16—H16	0.9300	C34—H34C	0.9600
C17—C18	1.364 (3)
C9—N1—C2	111.7 (1)	C16—C17—H17	120.1
C9—N1—H1	124.1	C17—C18—C19	120.4 (2)
C2—N1—H1	124.1	C17—C18—H18	119.8
C3—C2—C7	122.31 (16)	C19—C18—H18	119.8
C3—C2—N1	128.32 (15)	C14—C19—C18	121.0 (2)
C7—C2—N1	109.30 (14)	C14—C19—H19	119.5
C2—C3—C4	117.17 (17)	C18—C19—H19	119.5
C2—C3—H3	121.4	N21—C20—C13	108.15 (13)
C4—C3—H3	121.4	N21—C20—H20A	110.1
C5—C4—C3	121.91 (18)	C13—C20—H20A	110.1
C5—C4—H4	119.0	N21—C20—H20B	110.1
C3—C4—H4	119.0	C13—C20—H20B	110.1
C4—C5—C6	120.21 (19)	H20A—C20—H20B	108.4
C4—C5—H5	119.9	C22—N21—C34	110.82 (13)
C6—C5—H5	119.9	C22—N21—C20	110.42 (13)
C7—C6—C5	119.03 (17)	C34—N21—C20	113.43 (14)
C7—C6—H6	120.5	N21—C22—C23	112.47 (13)
C5—C6—H6	120.5	N21—C22—H22A	109.1
C6—C7—C2	119.31 (15)	C23—C22—H22A	109.1
C6—C7—C8	131.03 (15)	N21—C22—H22B	109.1
C2—C7—C8	109.59 (14)	C23—C22—H22B	109.1
N10—C8—C7	111.51 (13)	H22A—C22—H22B	107.8
N10—C8—C9	112.07 (13)	C25—C23—C24	116.89 (15)
C7—C8—C9	100.76 (12)	C25—C23—C22	124.05 (15)
N10—C8—C13	103.36 (12)	C24—C23—C22	119.05 (14)
C7—C8—C13	117.37 (13)	O35—C24—C23	121.16 (15)
C9—C8—C13	112.12 (13)	O35—C24—C13	121.49 (15)
O32—C9—N1	125.69 (15)	C23—C24—C13	117.35 (13)
O32—C9—C8	125.47 (14)	C23—C25—C26	129.24 (16)
N1—C9—C8	108.54 (14)	C23—C25—H25	115.4
C11—N10—C33	116.2 (2)	C26—C25—H25	115.4
C11—N10—C8	107.4 (1)	C27—C26—C31	117.24 (17)
C33—N10—C8	115.6 (1)	C27—C26—C25	124.21 (16)
N10—C11—C12	101.72 (13)	C31—C26—C25	118.50 (16)
N10—C11—H11A	111.4	C28—C27—C26	121.20 (19)
C12—C11—H11A	111.4	C28—C27—H27	119.4
N10—C11—H11B	111.4	C26—C27—H27	119.4
C12—C11—H11B	111.4	C29—C28—C27	120.2 (2)
H11A—C11—H11B	109.3	C29—C28—H28	119.9
C11—C12—C14	117.70 (14)	C27—C28—H28	119.9
C11—C12—C13	103.29 (13)	C28—C29—C30	119.7 (2)
C14—C12—C13	114.87 (13)	C28—C29—H29	120.1
C11—C12—H12	106.8	C30—C29—H29	120.1
C14—C12—H12	106.8	C29—C30—C31	120.1 (2)
C13—C12—H12	106.8	C29—C30—H30	119.9
C20—C13—C24	106.35 (13)	C31—C30—H30	119.9
C20—C13—C12	113.18 (13)	C30—C31—C26	121.4 (2)
C24—C13—C12	111.77 (12)	C30—C31—H31	119.3
C20—C13—C8	111.88 (12)	C26—C31—H31	119.3
C24—C13—C8	110.33 (13)	N10—C33—H33A	109.5
C12—C13—C8	103.43 (12)	N10—C33—H33B	109.5
C19—C14—C15	117.31 (17)	H33A—C33—H33B	109.5
C19—C14—C12	123.45 (17)	N10—C33—H33C	109.5
C15—C14—C12	119.24 (15)	H33A—C33—H33C	109.5
C16—C15—C14	121.54 (19)	H33B—C33—H33C	109.5
C16—C15—H15	119.2	N21—C34—H34A	109.5
C14—C15—H15	119.2	N21—C34—H34B	109.5
C17—C16—C15	120.0 (2)	H34A—C34—H34B	109.5
C17—C16—H16	120.0	N21—C34—H34C	109.5
C15—C16—H16	120.0	H34A—C34—H34C	109.5
C18—C17—C16	119.7 (2)	H34B—C34—H34C	109.5
C18—C17—H17	120.1
C9—N1—C2—C3	−179.57 (18)	C9—C8—C13—C24	124.06 (14)
C9—N1—C2—C7	−2.7 (2)	N10—C8—C13—C12	4.63 (15)
C7—C2—C3—C4	−1.0 (3)	C7—C8—C13—C12	127.80 (13)
N1—C2—C3—C4	175.45 (18)	C9—C8—C13—C12	−116.27 (13)
C2—C3—C4—C5	−0.8 (3)	C11—C12—C14—C19	27.2 (2)
C3—C4—C5—C6	0.8 (3)	C13—C12—C14—C19	−94.7 (2)
C4—C5—C6—C7	1.0 (3)	C11—C12—C14—C15	−153.02 (16)
C5—C6—C7—C2	−2.8 (3)	C13—C12—C14—C15	85.01 (19)
C5—C6—C7—C8	−179.31 (18)	C19—C14—C15—C16	0.5 (3)
C3—C2—C7—C6	2.8 (3)	C12—C14—C15—C16	−179.23 (16)
N1—C2—C7—C6	−174.22 (15)	C14—C15—C16—C17	−0.5 (3)
C3—C2—C7—C8	−179.93 (16)	C15—C16—C17—C18	0.2 (3)
N1—C2—C7—C8	3.01 (19)	C16—C17—C18—C19	0.0 (3)
C6—C7—C8—N10	55.6 (2)	C15—C14—C19—C18	−0.3 (3)
C2—C7—C8—N10	−121.19 (15)	C12—C14—C19—C18	179.45 (16)
C6—C7—C8—C9	174.70 (18)	C17—C18—C19—C14	0.0 (3)
C2—C7—C8—C9	−2.11 (17)	C24—C13—C20—N21	−63.73 (16)
C6—C7—C8—C13	−63.3 (2)	C12—C13—C20—N21	173.18 (13)
C2—C7—C8—C13	119.89 (15)	C8—C13—C20—N21	56.81 (17)
C2—N1—C9—O32	175.26 (17)	C13—C20—N21—C22	74.10 (17)
C2—N1—C9—C8	1.29 (19)	C13—C20—N21—C34	−160.82 (15)
N10—C8—C9—O32	−54.8 (2)	C34—N21—C22—C23	−178.47 (15)
C7—C8—C9—O32	−173.49 (17)	C20—N21—C22—C23	−51.93 (19)
C13—C8—C9—O32	60.9 (2)	N21—C22—C23—C25	−152.55 (17)
N10—C8—C9—N1	119.16 (15)	N21—C22—C23—C24	25.7 (2)
C7—C8—C9—N1	0.50 (17)	C25—C23—C24—O35	−22.8 (2)
C13—C8—C9—N1	−125.12 (14)	C22—C23—C24—O35	158.76 (16)
C7—C8—N10—C11	−158.55 (13)	C25—C23—C24—C13	157.76 (15)
C9—C8—N10—C11	89.34 (16)	C22—C23—C24—C13	−20.6 (2)
C13—C8—N10—C11	−31.58 (16)	C20—C13—C24—O35	−141.51 (16)
C7—C8—N10—C33	69.85 (19)	C12—C13—C24—O35	−17.5 (2)
C9—C8—N10—C33	−42.3 (2)	C8—C13—C24—O35	96.96 (18)
C13—C8—N10—C33	−163.18 (14)	C20—C13—C24—C23	37.87 (18)
C33—N10—C11—C12	177.85 (14)	C12—C13—C24—C23	161.85 (14)
C8—N10—C11—C12	46.58 (16)	C8—C13—C24—C23	−83.65 (17)
N10—C11—C12—C14	−168.91 (13)	C24—C23—C25—C26	179.34 (16)
N10—C11—C12—C13	−41.18 (16)	C22—C23—C25—C26	−2.4 (3)
C11—C12—C13—C20	−99.21 (16)	C23—C25—C26—C27	−28.9 (3)
C14—C12—C13—C20	30.27 (19)	C23—C25—C26—C31	153.63 (19)
C11—C12—C13—C24	140.74 (14)	C31—C26—C27—C28	−2.4 (3)
C14—C12—C13—C24	−89.77 (17)	C25—C26—C27—C28	−179.94 (19)
C11—C12—C13—C8	22.05 (16)	C26—C27—C28—C29	1.3 (3)
C14—C12—C13—C8	151.54 (14)	C27—C28—C29—C30	0.9 (4)
N10—C8—C13—C20	126.76 (13)	C28—C29—C30—C31	−1.9 (4)
C7—C8—C13—C20	−110.06 (15)	C29—C30—C31—C26	0.7 (3)
C9—C8—C13—C20	5.87 (17)	C27—C26—C31—C30	1.4 (3)
N10—C8—C13—C24	−115.05 (13)	C25—C26—C31—C30	179.10 (19)
C7—C8—C13—C24	8.12 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O35	0.98	2.33	2.804 (2)	109
C20—H20B···O32	0.97	2.35	2.898 (2)	115
C25—H25···O35	0.93	2.41	2.770 (2)	103
N1—H1···O32^i	0.86	2.06	2.883 (2)	159
C28—H28···N10^ii	0.93	2.61	3.520 (3)	168

Symmetry codes: (i) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2.