1''-Benzyl-1'-methyl-4'-(naphthalen-1-yl)naphthalene-2-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-1,2''-dione.

In the title compound, C(38)H(32)N(2)O(2), the pyrrolidine ring adopts an envelope conformation, whereas the cyclo-hexa-none ring in the tetra-hydro-naphthalene fused-ring system adopts a half-chair conformation. The benzyl ring is oriented at an angle of 67.1 (1)° with respect to the naphthyl ring system. Four intra-molecular C-H⋯O close contacts and C-H⋯π inter-action are observed. In the crystal, mol-ecules associate via C-H⋯O hydrogen bonds, forming a C(12) chain motif along the ac plane.

Related literature

For general background to pyrrolidine derivatives, see: Mendoza et al. (2011 ▶); Morais et al. (2009 ▶); Pettersson et al. (2011 ▶); Shi et al. (2011 ▶). For a related structure, see: Selvanayagam et al. (2011 ▶). For the superposition of related structures, see: Gans & Shalloway (2001 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C38H32N2O2

M = 548.66

Monoclinic,

a = 12.6084 (6) Å

b = 14.3751 (7) Å

c = 17.4021 (9) Å

β = 110.057 (1)°

V = 2962.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

7081 measured reflections

7081 independent reflections

4812 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.149

S = 1.06

7081 reflections

380 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021908/ng5180sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021908/ng5180Isup2.hkl

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

C38H32N2O2	F(000) = 1160
Mr = 548.66	Dx = 1.230 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19526 reflections
a = 12.6084 (6) Å	θ = 2.4–28.3°
b = 14.3751 (7) Å	µ = 0.08 mm−1
c = 17.4021 (9) Å	T = 292 K
β = 110.057 (1)°	Block, colourless
V = 2962.8 (3) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 28.0°, θmin = 1.7°
ω scans	h = −16→15
7081 measured reflections	k = 0→18
7081 independent reflections	l = 0→22

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.6156P] where P = (Fo2 + 2Fc2)/3
7081 reflections	(Δ/σ)max < 0.001
380 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.14 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 > 2sigma(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	0.66021 (11)	0.12013 (10)	0.16760 (9)	0.0662 (4)
O2	0.93723 (11)	0.40608 (9)	0.17479 (8)	0.0626 (4)
N1	0.90128 (12)	0.19586 (10)	0.24061 (8)	0.0493 (4)
N2	0.73609 (12)	0.08330 (10)	0.06975 (9)	0.0515 (4)
C1	0.82372 (13)	0.20914 (12)	0.15647 (10)	0.0438 (4)
C2	0.77474 (14)	0.31053 (12)	0.15932 (10)	0.0440 (4)
C3	0.79927 (15)	0.32572 (12)	0.25429 (10)	0.0483 (4)
H3	0.8622	0.3698	0.2731	0.058*
C4	0.84428 (17)	0.23271 (13)	0.29382 (11)	0.0579 (5)
H4A	0.8965	0.2410	0.3492	0.069*
H4B	0.7833	0.1922	0.2949	0.069*
C5	0.72848 (14)	0.13465 (12)	0.13340 (11)	0.0478 (4)
C6	0.82563 (15)	0.11410 (13)	0.04566 (10)	0.0500 (4)
C7	0.8606 (2)	0.07633 (15)	−0.01446 (12)	0.0656 (6)
H7	0.8223	0.0270	−0.0467	0.079*
C8	0.9545 (2)	0.11472 (18)	−0.02475 (14)	0.0774 (7)
H8	0.9791	0.0918	−0.0658	0.093*
C9	1.0130 (2)	0.18583 (18)	0.02375 (15)	0.0766 (7)
H9	1.0775	0.2093	0.0161	0.092*
C10	0.97681 (16)	0.22356 (15)	0.08476 (13)	0.0617 (5)
H10	1.0168	0.2716	0.1179	0.074*
C11	0.88083 (14)	0.18802 (12)	0.09463 (11)	0.0467 (4)
C12	0.64951 (14)	0.32215 (14)	0.10675 (11)	0.0537 (5)
H12A	0.6056	0.2749	0.1221	0.064*
H12B	0.6235	0.3824	0.1180	0.064*
C13	0.62867 (17)	0.31449 (15)	0.01543 (12)	0.0623 (5)
H13A	0.6496	0.2528	0.0031	0.075*
H13B	0.5490	0.3233	−0.0149	0.075*
C14	0.69571 (18)	0.38566 (14)	−0.01072 (12)	0.0599 (5)
C15	0.6569 (2)	0.42401 (19)	−0.08921 (14)	0.0832 (7)
H15	0.5878	0.4050	−0.1263	0.100*
C16	0.7195 (3)	0.4893 (2)	−0.11224 (16)	0.1014 (9)
H16	0.6921	0.5144	−0.1647	0.122*
C17	0.8221 (3)	0.51820 (19)	−0.05876 (17)	0.0964 (8)
H17	0.8643	0.5621	−0.0750	0.116*
C18	0.8620 (2)	0.48169 (15)	0.01912 (14)	0.0729 (6)
H18	0.9314	0.5012	0.0555	0.087*
C19	0.79923 (17)	0.41576 (13)	0.04390 (11)	0.0549 (5)
C20	0.84519 (15)	0.38003 (12)	0.12938 (11)	0.0478 (4)
C21	0.70292 (15)	0.36805 (13)	0.27567 (10)	0.0517 (4)
C22	0.69140 (15)	0.46686 (14)	0.27729 (10)	0.0518 (4)
C23	0.77083 (18)	0.52959 (14)	0.26515 (12)	0.0609 (5)
H23	0.8326	0.5062	0.2537	0.073*
C24	0.7590 (2)	0.62308 (16)	0.26981 (15)	0.0765 (6)
H24	0.8134	0.6626	0.2628	0.092*
C25	0.6657 (3)	0.66048 (18)	0.28506 (16)	0.0879 (8)
H25	0.6581	0.7246	0.2879	0.106*
C26	0.5871 (2)	0.60358 (19)	0.29565 (15)	0.0805 (7)
H26	0.5245	0.6292	0.3045	0.097*
C27	0.59733 (16)	0.50575 (16)	0.29370 (11)	0.0614 (5)
C28	0.51909 (18)	0.4461 (2)	0.30987 (13)	0.0741 (6)
H28	0.4570	0.4710	0.3199	0.089*
C29	0.53320 (19)	0.3533 (2)	0.31101 (14)	0.0767 (7)
H29	0.4823	0.3147	0.3237	0.092*
C30	0.62455 (18)	0.31407 (16)	0.29314 (13)	0.0679 (6)
H30	0.6318	0.2497	0.2932	0.082*
C31	0.94324 (17)	0.10143 (13)	0.26161 (12)	0.0614 (5)
H31A	0.8823	0.0617	0.2622	0.092*
H31B	1.0009	0.1013	0.3147	0.092*
H31C	0.9741	0.0791	0.2218	0.092*
C32	0.65854 (17)	0.00833 (14)	0.03219 (13)	0.0641 (5)
H32A	0.6339	0.0158	−0.0267	0.077*
H32B	0.5924	0.0144	0.0483	0.077*
C33	0.70527 (15)	−0.08882 (13)	0.05326 (11)	0.0532 (4)
C34	0.64882 (19)	−0.16142 (15)	0.00444 (14)	0.0710 (6)
H34	0.5845	−0.1495	−0.0406	0.085*
C35	0.6867 (2)	−0.25106 (17)	0.02169 (16)	0.0816 (7)
H35	0.6479	−0.2993	−0.0118	0.098*
C36	0.7813 (2)	−0.27023 (16)	0.08771 (16)	0.0784 (7)
H36	0.8065	−0.3312	0.0991	0.094*
C37	0.83818 (19)	−0.19893 (16)	0.13677 (14)	0.0720 (6)
H37	0.9024	−0.2113	0.1817	0.086*
C38	0.80016 (17)	−0.10885 (14)	0.11940 (13)	0.0629 (5)
H38	0.8393	−0.0607	0.1530	0.076*

	U11	U22	U33	U12	U13	U23
O1	0.0568 (8)	0.0683 (9)	0.0841 (10)	−0.0130 (7)	0.0380 (8)	−0.0036 (7)
O2	0.0576 (8)	0.0656 (9)	0.0608 (8)	−0.0172 (7)	0.0154 (7)	−0.0010 (7)
N1	0.0483 (8)	0.0490 (9)	0.0456 (8)	0.0023 (7)	0.0097 (7)	0.0001 (7)
N2	0.0499 (8)	0.0495 (9)	0.0508 (8)	−0.0032 (7)	0.0117 (7)	−0.0047 (7)
C1	0.0390 (9)	0.0460 (10)	0.0470 (9)	−0.0018 (7)	0.0155 (7)	−0.0007 (7)
C2	0.0414 (9)	0.0457 (10)	0.0443 (9)	−0.0004 (7)	0.0141 (7)	−0.0012 (7)
C3	0.0493 (10)	0.0500 (10)	0.0453 (9)	−0.0027 (8)	0.0160 (8)	−0.0040 (8)
C4	0.0690 (12)	0.0570 (12)	0.0454 (10)	0.0044 (10)	0.0167 (9)	0.0002 (9)
C5	0.0423 (9)	0.0468 (10)	0.0527 (10)	0.0004 (8)	0.0140 (8)	0.0012 (8)
C6	0.0523 (10)	0.0520 (11)	0.0436 (9)	0.0109 (9)	0.0140 (8)	0.0058 (8)
C7	0.0815 (15)	0.0681 (13)	0.0490 (11)	0.0195 (11)	0.0246 (11)	0.0034 (9)
C8	0.0981 (18)	0.0828 (17)	0.0657 (14)	0.0330 (15)	0.0466 (14)	0.0160 (13)
C9	0.0690 (14)	0.0885 (17)	0.0916 (17)	0.0188 (13)	0.0526 (13)	0.0307 (14)
C10	0.0527 (11)	0.0637 (13)	0.0761 (13)	0.0049 (9)	0.0317 (10)	0.0120 (10)
C11	0.0443 (9)	0.0488 (10)	0.0492 (9)	0.0069 (8)	0.0187 (8)	0.0056 (8)
C12	0.0433 (9)	0.0569 (11)	0.0580 (11)	0.0025 (8)	0.0134 (8)	−0.0015 (9)
C13	0.0527 (11)	0.0684 (13)	0.0542 (11)	0.0060 (10)	0.0033 (9)	−0.0027 (10)
C14	0.0675 (12)	0.0586 (12)	0.0504 (11)	0.0119 (10)	0.0160 (10)	−0.0013 (9)
C15	0.0942 (17)	0.0917 (18)	0.0537 (13)	0.0162 (14)	0.0124 (12)	0.0073 (12)
C16	0.135 (3)	0.105 (2)	0.0610 (15)	0.0160 (19)	0.0290 (17)	0.0285 (15)
C17	0.131 (2)	0.0851 (18)	0.0820 (18)	−0.0011 (17)	0.0482 (18)	0.0265 (15)
C18	0.0921 (16)	0.0630 (13)	0.0680 (13)	−0.0038 (12)	0.0330 (12)	0.0080 (11)
C19	0.0675 (12)	0.0478 (10)	0.0519 (10)	0.0057 (9)	0.0239 (10)	0.0016 (8)
C20	0.0507 (10)	0.0421 (9)	0.0504 (10)	0.0001 (8)	0.0169 (8)	−0.0024 (8)
C21	0.0510 (10)	0.0605 (12)	0.0443 (9)	−0.0029 (9)	0.0171 (8)	−0.0057 (8)
C22	0.0532 (10)	0.0608 (12)	0.0390 (9)	0.0068 (9)	0.0128 (8)	0.0000 (8)
C23	0.0669 (12)	0.0585 (12)	0.0603 (12)	0.0074 (10)	0.0257 (10)	0.0012 (9)
C24	0.0913 (17)	0.0583 (14)	0.0811 (15)	0.0064 (12)	0.0308 (13)	0.0062 (11)
C25	0.103 (2)	0.0639 (15)	0.0899 (18)	0.0290 (15)	0.0238 (15)	0.0018 (13)
C26	0.0754 (15)	0.0865 (18)	0.0754 (15)	0.0311 (14)	0.0203 (13)	−0.0077 (13)
C27	0.0520 (11)	0.0837 (15)	0.0439 (10)	0.0148 (10)	0.0106 (8)	−0.0056 (10)
C28	0.0530 (12)	0.111 (2)	0.0603 (13)	0.0049 (13)	0.0225 (10)	−0.0180 (13)
C29	0.0623 (13)	0.104 (2)	0.0727 (14)	−0.0181 (13)	0.0348 (12)	−0.0180 (13)
C30	0.0674 (13)	0.0735 (14)	0.0693 (13)	−0.0117 (11)	0.0315 (11)	−0.0112 (11)
C31	0.0615 (12)	0.0543 (12)	0.0606 (12)	0.0076 (9)	0.0108 (10)	0.0055 (9)
C32	0.0551 (11)	0.0584 (12)	0.0620 (12)	−0.0054 (9)	−0.0014 (9)	−0.0089 (9)
C33	0.0514 (10)	0.0530 (11)	0.0536 (10)	−0.0078 (9)	0.0157 (9)	−0.0054 (9)
C34	0.0669 (13)	0.0632 (14)	0.0726 (14)	−0.0075 (11)	0.0108 (11)	−0.0107 (11)
C35	0.0861 (17)	0.0606 (14)	0.0941 (17)	−0.0160 (13)	0.0257 (15)	−0.0181 (13)
C36	0.0867 (17)	0.0550 (13)	0.0996 (18)	0.0026 (12)	0.0399 (15)	0.0072 (12)
C37	0.0688 (14)	0.0680 (14)	0.0741 (14)	0.0012 (11)	0.0180 (11)	0.0129 (12)
C38	0.0624 (12)	0.0567 (12)	0.0615 (12)	−0.0075 (10)	0.0107 (10)	−0.0039 (10)

O1—C5	1.221 (2)	C17—C18	1.378 (3)
O2—C20	1.218 (2)	C17—H17	0.9300
N1—C4	1.453 (2)	C18—C19	1.394 (3)
N1—C31	1.457 (2)	C18—H18	0.9300
N1—C1	1.468 (2)	C19—C20	1.490 (3)
N2—C5	1.362 (2)	C21—C30	1.370 (3)
N2—C6	1.404 (2)	C21—C22	1.429 (3)
N2—C32	1.451 (2)	C22—C23	1.416 (3)
C1—C11	1.517 (2)	C22—C27	1.426 (3)
C1—C5	1.555 (2)	C23—C24	1.358 (3)
C1—C2	1.590 (2)	C23—H23	0.9300
C2—C12	1.539 (2)	C24—C25	1.398 (3)
C2—C20	1.541 (2)	C24—H24	0.9300
C2—C3	1.589 (2)	C25—C26	1.346 (4)
C3—C21	1.515 (2)	C25—H25	0.9300
C3—C4	1.522 (3)	C26—C27	1.414 (3)
C3—H3	0.9800	C26—H26	0.9300
C4—H4A	0.9700	C27—C28	1.407 (3)
C4—H4B	0.9700	C28—C29	1.345 (3)
C6—C7	1.379 (3)	C28—H28	0.9300
C6—C11	1.390 (3)	C29—C30	1.409 (3)
C7—C8	1.372 (3)	C29—H29	0.9300
C7—H7	0.9300	C30—H30	0.9300
C8—C9	1.369 (3)	C31—H31A	0.9600
C8—H8	0.9300	C31—H31B	0.9600
C9—C10	1.401 (3)	C31—H31C	0.9600
C9—H9	0.9300	C32—C33	1.511 (3)
C10—C11	1.378 (2)	C32—H32A	0.9700
C10—H10	0.9300	C32—H32B	0.9700
C12—C13	1.523 (3)	C33—C38	1.376 (3)
C12—H12A	0.9700	C33—C34	1.379 (3)
C12—H12B	0.9700	C34—C35	1.371 (3)
C13—C14	1.494 (3)	C34—H34	0.9300
C13—H13A	0.9700	C35—C36	1.370 (3)
C13—H13B	0.9700	C35—H35	0.9300
C14—C19	1.394 (3)	C36—C37	1.369 (3)
C14—C15	1.397 (3)	C36—H36	0.9300
C15—C16	1.372 (4)	C37—C38	1.378 (3)
C15—H15	0.9300	C37—H37	0.9300
C16—C17	1.373 (4)	C38—H38	0.9300
C16—H16	0.9300
C4—N1—C31	113.34 (15)	C16—C17—C18	119.5 (3)
C4—N1—C1	106.40 (13)	C16—C17—H17	120.2
C31—N1—C1	115.58 (14)	C18—C17—H17	120.2
C5—N2—C6	111.11 (14)	C17—C18—C19	120.6 (2)
C5—N2—C32	122.98 (16)	C17—C18—H18	119.7
C6—N2—C32	125.90 (16)	C19—C18—H18	119.7
N1—C1—C11	111.45 (13)	C18—C19—C14	119.87 (19)
N1—C1—C5	111.05 (13)	C18—C19—C20	118.38 (18)
C11—C1—C5	101.04 (13)	C14—C19—C20	121.75 (17)
N1—C1—C2	102.78 (13)	O2—C20—C19	119.97 (17)
C11—C1—C2	119.30 (14)	O2—C20—C2	120.77 (16)
C5—C1—C2	111.43 (13)	C19—C20—C2	119.26 (15)
C12—C2—C20	108.76 (14)	C30—C21—C22	118.20 (18)
C12—C2—C3	113.42 (14)	C30—C21—C3	121.82 (18)
C20—C2—C3	109.47 (13)	C22—C21—C3	119.98 (16)
C12—C2—C1	114.28 (14)	C23—C22—C27	117.36 (18)
C20—C2—C1	107.98 (13)	C23—C22—C21	123.22 (17)
C3—C2—C1	102.66 (13)	C27—C22—C21	119.40 (18)
C21—C3—C4	116.62 (15)	C24—C23—C22	121.6 (2)
C21—C3—C2	115.11 (14)	C24—C23—H23	119.2
C4—C3—C2	105.01 (14)	C22—C23—H23	119.2
C21—C3—H3	106.5	C23—C24—C25	120.6 (2)
C4—C3—H3	106.5	C23—C24—H24	119.7
C2—C3—H3	106.5	C25—C24—H24	119.7
N1—C4—C3	102.79 (14)	C26—C25—C24	120.0 (2)
N1—C4—H4A	111.2	C26—C25—H25	120.0
C3—C4—H4A	111.2	C24—C25—H25	120.0
N1—C4—H4B	111.2	C25—C26—C27	121.5 (2)
C3—C4—H4B	111.2	C25—C26—H26	119.2
H4A—C4—H4B	109.1	C27—C26—H26	119.2
O1—C5—N2	124.20 (16)	C28—C27—C26	121.7 (2)
O1—C5—C1	127.08 (16)	C28—C27—C22	119.3 (2)
N2—C5—C1	108.64 (15)	C26—C27—C22	119.0 (2)
C7—C6—C11	122.88 (18)	C29—C28—C27	120.6 (2)
C7—C6—N2	127.01 (18)	C29—C28—H28	119.7
C11—C6—N2	110.04 (15)	C27—C28—H28	119.7
C8—C7—C6	117.1 (2)	C28—C29—C30	120.5 (2)
C8—C7—H7	121.4	C28—C29—H29	119.8
C6—C7—H7	121.4	C30—C29—H29	119.8
C7—C8—C9	121.8 (2)	C21—C30—C29	121.9 (2)
C7—C8—H8	119.1	C21—C30—H30	119.0
C9—C8—H8	119.1	C29—C30—H30	119.0
C8—C9—C10	120.6 (2)	N1—C31—H31A	109.5
C8—C9—H9	119.7	N1—C31—H31B	109.5
C10—C9—H9	119.7	H31A—C31—H31B	109.5
C11—C10—C9	118.7 (2)	N1—C31—H31C	109.5
C11—C10—H10	120.7	H31A—C31—H31C	109.5
C9—C10—H10	120.7	H31B—C31—H31C	109.5
C10—C11—C6	118.91 (17)	N2—C32—C33	115.50 (15)
C10—C11—C1	131.72 (17)	N2—C32—H32A	108.4
C6—C11—C1	109.17 (15)	C33—C32—H32A	108.4
C13—C12—C2	112.77 (15)	N2—C32—H32B	108.4
C13—C12—H12A	109.0	C33—C32—H32B	108.4
C2—C12—H12A	109.0	H32A—C32—H32B	107.5
C13—C12—H12B	109.0	C38—C33—C34	118.27 (19)
C2—C12—H12B	109.0	C38—C33—C32	123.44 (17)
H12A—C12—H12B	107.8	C34—C33—C32	118.29 (17)
C14—C13—C12	110.80 (16)	C35—C34—C33	120.6 (2)
C14—C13—H13A	109.5	C35—C34—H34	119.7
C12—C13—H13A	109.5	C33—C34—H34	119.7
C14—C13—H13B	109.5	C36—C35—C34	120.7 (2)
C12—C13—H13B	109.5	C36—C35—H35	119.7
H13A—C13—H13B	108.1	C34—C35—H35	119.7
C19—C14—C15	118.5 (2)	C37—C36—C35	119.4 (2)
C19—C14—C13	120.00 (17)	C37—C36—H36	120.3
C15—C14—C13	121.5 (2)	C35—C36—H36	120.3
C16—C15—C14	120.8 (2)	C36—C37—C38	119.9 (2)
C16—C15—H15	119.6	C36—C37—H37	120.1
C14—C15—H15	119.6	C38—C37—H37	120.1
C15—C16—C17	120.8 (2)	C33—C38—C37	121.15 (19)
C15—C16—H16	119.6	C33—C38—H38	119.4
C17—C16—H16	119.6	C37—C38—H38	119.4
C4—N1—C1—C11	170.62 (14)	C12—C13—C14—C19	30.5 (2)
C31—N1—C1—C11	−62.61 (19)	C12—C13—C14—C15	−149.0 (2)
C4—N1—C1—C5	−77.56 (16)	C19—C14—C15—C16	0.4 (3)
C31—N1—C1—C5	49.21 (19)	C13—C14—C15—C16	180.0 (2)
C4—N1—C1—C2	41.70 (16)	C14—C15—C16—C17	0.3 (4)
C31—N1—C1—C2	168.47 (14)	C15—C16—C17—C18	−0.6 (4)
N1—C1—C2—C12	−143.34 (14)	C16—C17—C18—C19	0.1 (4)
C11—C1—C2—C12	92.80 (18)	C17—C18—C19—C14	0.7 (3)
C5—C1—C2—C12	−24.3 (2)	C17—C18—C19—C20	−178.7 (2)
N1—C1—C2—C20	95.51 (15)	C15—C14—C19—C18	−0.9 (3)
C11—C1—C2—C20	−28.35 (19)	C13—C14—C19—C18	179.53 (19)
C5—C1—C2—C20	−145.49 (14)	C15—C14—C19—C20	178.45 (18)
N1—C1—C2—C3	−20.09 (15)	C13—C14—C19—C20	−1.1 (3)
C11—C1—C2—C3	−143.95 (14)	C18—C19—C20—O2	−2.5 (3)
C5—C1—C2—C3	98.91 (15)	C14—C19—C20—O2	178.12 (18)
C12—C2—C3—C21	−12.2 (2)	C18—C19—C20—C2	177.21 (17)
C20—C2—C3—C21	109.49 (17)	C14—C19—C20—C2	−2.2 (3)
C1—C2—C3—C21	−136.00 (15)	C12—C2—C20—O2	156.02 (17)
C12—C2—C3—C4	117.47 (16)	C3—C2—C20—O2	31.6 (2)
C20—C2—C3—C4	−120.87 (15)	C1—C2—C20—O2	−79.4 (2)
C1—C2—C3—C4	−6.35 (17)	C12—C2—C20—C19	−23.7 (2)
C31—N1—C4—C3	−174.48 (14)	C3—C2—C20—C19	−148.10 (15)
C1—N1—C4—C3	−46.38 (17)	C1—C2—C20—C19	100.85 (17)
C21—C3—C4—N1	159.66 (15)	C4—C3—C21—C30	−31.4 (2)
C2—C3—C4—N1	30.92 (17)	C2—C3—C21—C30	92.3 (2)
C6—N2—C5—O1	−177.45 (17)	C4—C3—C21—C22	149.21 (17)
C32—N2—C5—O1	3.8 (3)	C2—C3—C21—C22	−87.09 (19)
C6—N2—C5—C1	−0.32 (19)	C30—C21—C22—C23	176.09 (18)
C32—N2—C5—C1	−179.08 (15)	C3—C21—C22—C23	−4.5 (3)
N1—C1—C5—O1	58.9 (2)	C30—C21—C22—C27	−2.4 (3)
C11—C1—C5—O1	177.17 (17)	C3—C21—C22—C27	177.04 (15)
C2—C1—C5—O1	−55.1 (2)	C27—C22—C23—C24	0.7 (3)
N1—C1—C5—N2	−118.17 (15)	C21—C22—C23—C24	−177.78 (19)
C11—C1—C5—N2	0.15 (17)	C22—C23—C24—C25	−1.5 (3)
C2—C1—C5—N2	127.90 (15)	C23—C24—C25—C26	0.3 (4)
C5—N2—C6—C7	177.43 (18)	C24—C25—C26—C27	1.5 (4)
C32—N2—C6—C7	−3.9 (3)	C25—C26—C27—C28	175.9 (2)
C5—N2—C6—C11	0.4 (2)	C25—C26—C27—C22	−2.2 (3)
C32—N2—C6—C11	179.10 (16)	C23—C22—C27—C28	−177.11 (17)
C11—C6—C7—C8	0.2 (3)	C21—C22—C27—C28	1.5 (3)
N2—C6—C7—C8	−176.48 (18)	C23—C22—C27—C26	1.0 (3)
C6—C7—C8—C9	1.6 (3)	C21—C22—C27—C26	179.63 (18)
C7—C8—C9—C10	−1.6 (3)	C26—C27—C28—C29	−177.2 (2)
C8—C9—C10—C11	−0.4 (3)	C22—C27—C28—C29	0.9 (3)
C9—C10—C11—C6	2.1 (3)	C27—C28—C29—C30	−2.3 (3)
C9—C10—C11—C1	176.24 (18)	C22—C21—C30—C29	1.1 (3)
C7—C6—C11—C10	−2.1 (3)	C3—C21—C30—C29	−178.35 (18)
N2—C6—C11—C10	175.08 (16)	C28—C29—C30—C21	1.3 (3)
C7—C6—C11—C1	−177.46 (16)	C5—N2—C32—C33	−105.3 (2)
N2—C6—C11—C1	−0.28 (19)	C6—N2—C32—C33	76.1 (2)
N1—C1—C11—C10	−56.4 (2)	N2—C32—C33—C38	17.9 (3)
C5—C1—C11—C10	−174.47 (19)	N2—C32—C33—C34	−163.17 (19)
C2—C1—C11—C10	63.1 (3)	C38—C33—C34—C35	0.0 (3)
N1—C1—C11—C6	118.11 (15)	C32—C33—C34—C35	−179.0 (2)
C5—C1—C11—C6	0.08 (17)	C33—C34—C35—C36	0.0 (4)
C2—C1—C11—C6	−122.36 (16)	C34—C35—C36—C37	0.0 (4)
C20—C2—C12—C13	53.7 (2)	C35—C36—C37—C38	0.0 (4)
C3—C2—C12—C13	175.74 (15)	C34—C33—C38—C37	−0.1 (3)
C1—C2—C12—C13	−67.0 (2)	C32—C33—C38—C37	178.8 (2)
C2—C12—C13—C14	−58.2 (2)	C36—C37—C38—C33	0.1 (3)

Cg is the centroid of the N2/C5/C1/C11/C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1i	0.93	2.54	3.399 (3)	154
C3—H3···O2	0.98	2.28	2.815 (2)	113
C4—H4B···O1	0.97	2.46	3.055 (2)	120
C10—H10···O2	0.93	2.53	3.182 (3)	127
C12—H12A···O1	0.97	2.38	3.078 (2)	128
C13—H13A···Cg	0.97	2.56	3.238 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2/C5/C1/C11/C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O1i	0.93	2.54	3.399 (3)	154
C3—H3⋯O2	0.98	2.28	2.815 (2)	113
C4—H4B⋯O1	0.97	2.46	3.055 (2)	120
C10—H10⋯O2	0.93	2.53	3.182 (3)	127
C12—H12A⋯O1	0.97	2.38	3.078 (2)	128
C13—H13A⋯Cg	0.97	2.56	3.238 (2)	127

Symmetry code: (i) .