1',1''-Dimethyl-4'-(naphthalen-1-yl)-1,2,3,4-tetra-hydro-naphthalene-2-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-1,2''-dione.

In the title compound, C(32)H(28)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 oxindole ring system is oriented at an angle of 48.2 (1)° with respect to the naphthyl ring system. An intra-molecular C-H⋯O close contact is observed. In the crystal, mol-ecules associate via two C-H⋯O hydrogen bonds, forming R(2) (2)(14) and R(2) (2)(10) dimers.

Related literature

For general background to pyrrolidine derivatives, see: Obniska et al. (2003 ▶); Peddi et al. (2004 ▶); Kaminski & Obniska (2008 ▶); Stylianakis et al. (2003 ▶). For related structures, see: Selvanayagam et al. (2011 ▶); Gans & Shalloway (2001 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C32H28N2O2

M = 472.56

Monoclinic,

a = 8.7529 (8) Å

b = 18.0411 (16) Å

c = 15.4489 (13) Å

β = 98.181 (2)°

V = 2414.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

27968 measured reflections

5745 independent reflections

4389 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.141

S = 1.04

5745 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.18 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 datablocks I, global. DOI: 10.1107/S1600536811007124/ng5125sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007124/ng5125Isup2.hkl

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

C32H28N2O2	F(000) = 1000
Mr = 472.56	Dx = 1.300 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17402 reflections
a = 8.7529 (8) Å	θ = 2.3–27.8°
b = 18.0411 (16) Å	µ = 0.08 mm−1
c = 15.4489 (13) Å	T = 292 K
β = 98.181 (2)°	Block, colourless
V = 2414.7 (4) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 28.0°, θmin = 1.8°
ω scans	h = −11→11
27968 measured reflections	k = −23→23
5745 independent 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) = 0.141	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.5875P] where P = (Fo2 + 2Fc2)/3
5745 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.18 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	0.19542 (14)	0.03811 (7)	0.02474 (7)	0.0503 (3)
O2	0.51135 (15)	0.18921 (7)	0.29060 (8)	0.0526 (3)
N1	0.17919 (14)	0.13236 (7)	0.18988 (8)	0.0394 (3)
N2	0.20315 (16)	−0.04854 (7)	0.13326 (9)	0.0447 (3)
C1	0.28805 (16)	0.07193 (8)	0.17953 (9)	0.0352 (3)
C2	0.43644 (16)	0.11610 (8)	0.16072 (9)	0.0341 (3)
C3	0.36697 (17)	0.19082 (8)	0.11804 (10)	0.0375 (3)
H3	0.4055	0.2308	0.1583	0.045*
C4	0.19270 (19)	0.18552 (9)	0.12043 (11)	0.0440 (4)
H4A	0.1507	0.2333	0.1336	0.053*
H4B	0.1390	0.1680	0.0649	0.053*
C5	0.22581 (17)	0.02033 (9)	0.10128 (10)	0.0393 (3)
C6	0.24558 (18)	−0.05153 (9)	0.22415 (11)	0.0410 (4)
C7	0.2350 (2)	−0.11139 (10)	0.27874 (13)	0.0528 (4)
H7	0.2003	−0.1573	0.2567	0.063*
C8	0.2781 (2)	−0.10037 (11)	0.36793 (13)	0.0558 (5)
H8	0.2723	−0.1397	0.4063	0.067*
C9	0.3292 (2)	−0.03231 (10)	0.40053 (12)	0.0517 (4)
H9	0.3571	−0.0261	0.4605	0.062*
C10	0.33951 (19)	0.02735 (9)	0.34430 (10)	0.0436 (4)
H10	0.3735	0.0733	0.3665	0.052*
C11	0.29901 (17)	0.01766 (8)	0.25571 (10)	0.0377 (3)
C12	0.53834 (18)	0.07288 (9)	0.10482 (10)	0.0386 (3)
H12A	0.4776	0.0604	0.0492	0.046*
H12B	0.6227	0.1044	0.0930	0.046*
C13	0.60428 (18)	0.00205 (9)	0.14878 (10)	0.0431 (4)
H13A	0.5209	−0.0326	0.1530	0.052*
H13B	0.6743	−0.0206	0.1132	0.052*
C14	0.68899 (17)	0.01682 (9)	0.23853 (10)	0.0417 (4)
C15	0.8018 (2)	−0.03200 (11)	0.27723 (13)	0.0542 (4)
H15	0.8222	−0.0751	0.2480	0.065*
C16	0.8835 (2)	−0.01708 (13)	0.35840 (14)	0.0660 (6)
H16	0.9577	−0.0505	0.3836	0.079*
C17	0.8563 (2)	0.04692 (13)	0.40262 (12)	0.0637 (5)
H17	0.9136	0.0571	0.4567	0.076*
C18	0.7440 (2)	0.09559 (11)	0.36647 (11)	0.0524 (4)
H18	0.7249	0.1385	0.3965	0.063*
C19	0.65839 (17)	0.08082 (9)	0.28461 (10)	0.0401 (4)
C20	0.53440 (17)	0.13366 (9)	0.24958 (10)	0.0382 (3)
C21	0.41452 (18)	0.21033 (9)	0.03005 (10)	0.0406 (4)
C22	0.55816 (19)	0.24838 (8)	0.02709 (11)	0.0427 (4)
C23	0.6600 (2)	0.26977 (10)	0.10265 (12)	0.0518 (4)
H23	0.6329	0.2604	0.1577	0.062*
C24	0.7977 (2)	0.30391 (12)	0.09610 (16)	0.0671 (6)
H24	0.8623	0.3179	0.1465	0.080*
C25	0.8418 (3)	0.31796 (13)	0.01394 (18)	0.0758 (7)
H25	0.9361	0.3405	0.0100	0.091*
C26	0.7475 (3)	0.29878 (12)	−0.05961 (16)	0.0697 (6)
H26	0.7779	0.3087	−0.1137	0.084*
C27	0.6039 (2)	0.26398 (9)	−0.05623 (12)	0.0514 (4)
C28	0.5078 (3)	0.24300 (11)	−0.13333 (12)	0.0621 (5)
H28	0.5378	0.2531	−0.1875	0.075*
C29	0.3724 (3)	0.20835 (11)	−0.12918 (12)	0.0635 (5)
H29	0.3092	0.1952	−0.1804	0.076*
C30	0.3263 (2)	0.19202 (10)	−0.04740 (12)	0.0531 (4)
H30	0.2327	0.1680	−0.0461	0.064*
C31	0.02001 (18)	0.10912 (10)	0.19308 (12)	0.0496 (4)
H31A	−0.0432	0.1520	0.1976	0.074*
H31B	0.0168	0.0777	0.2430	0.074*
H31C	−0.0180	0.0823	0.1407	0.074*
C32	0.1366 (3)	−0.10906 (10)	0.07871 (14)	0.0646 (6)
H32A	0.0785	−0.0895	0.0263	0.097*
H32B	0.0696	−0.1375	0.1100	0.097*
H32C	0.2176	−0.1403	0.0637	0.097*

	U11	U22	U33	U12	U13	U23
O1	0.0545 (7)	0.0563 (7)	0.0389 (6)	−0.0025 (6)	0.0017 (5)	−0.0018 (5)
O2	0.0589 (8)	0.0525 (7)	0.0462 (7)	0.0012 (6)	0.0059 (6)	−0.0133 (5)
N1	0.0365 (7)	0.0373 (7)	0.0465 (7)	0.0007 (5)	0.0127 (6)	0.0009 (6)
N2	0.0472 (8)	0.0365 (7)	0.0483 (8)	−0.0041 (6)	−0.0007 (6)	−0.0035 (6)
C1	0.0357 (7)	0.0356 (8)	0.0349 (7)	−0.0018 (6)	0.0076 (6)	−0.0006 (6)
C2	0.0347 (7)	0.0349 (7)	0.0336 (7)	−0.0014 (6)	0.0078 (6)	0.0007 (6)
C3	0.0393 (8)	0.0339 (7)	0.0398 (8)	−0.0011 (6)	0.0074 (6)	0.0011 (6)
C4	0.0404 (8)	0.0389 (8)	0.0540 (10)	0.0030 (7)	0.0109 (7)	0.0065 (7)
C5	0.0349 (7)	0.0417 (8)	0.0414 (8)	0.0003 (6)	0.0055 (6)	−0.0030 (6)
C6	0.0383 (8)	0.0369 (8)	0.0477 (9)	0.0009 (6)	0.0060 (7)	0.0013 (7)
C7	0.0543 (10)	0.0360 (9)	0.0670 (12)	−0.0017 (7)	0.0053 (9)	0.0053 (8)
C8	0.0585 (11)	0.0490 (10)	0.0606 (11)	0.0035 (8)	0.0110 (9)	0.0193 (9)
C9	0.0549 (10)	0.0589 (11)	0.0424 (9)	0.0032 (8)	0.0101 (8)	0.0100 (8)
C10	0.0478 (9)	0.0441 (9)	0.0407 (8)	−0.0018 (7)	0.0127 (7)	−0.0006 (7)
C11	0.0358 (7)	0.0373 (8)	0.0412 (8)	−0.0002 (6)	0.0098 (6)	0.0032 (6)
C12	0.0403 (8)	0.0439 (8)	0.0330 (7)	0.0014 (7)	0.0096 (6)	−0.0012 (6)
C13	0.0420 (8)	0.0433 (9)	0.0455 (9)	0.0052 (7)	0.0112 (7)	−0.0032 (7)
C14	0.0347 (7)	0.0479 (9)	0.0440 (8)	−0.0020 (7)	0.0103 (6)	0.0086 (7)
C15	0.0466 (9)	0.0540 (11)	0.0623 (11)	0.0049 (8)	0.0088 (8)	0.0130 (9)
C16	0.0513 (11)	0.0806 (15)	0.0640 (13)	0.0110 (10)	0.0009 (9)	0.0251 (11)
C17	0.0533 (11)	0.0942 (16)	0.0406 (9)	−0.0003 (10)	−0.0035 (8)	0.0144 (10)
C18	0.0491 (10)	0.0690 (12)	0.0391 (9)	−0.0066 (9)	0.0060 (7)	0.0030 (8)
C19	0.0352 (8)	0.0506 (9)	0.0352 (8)	−0.0050 (7)	0.0076 (6)	0.0051 (7)
C20	0.0379 (8)	0.0431 (8)	0.0351 (8)	−0.0056 (6)	0.0105 (6)	−0.0010 (6)
C21	0.0448 (9)	0.0344 (8)	0.0432 (8)	0.0011 (6)	0.0084 (7)	0.0069 (6)
C22	0.0469 (9)	0.0325 (8)	0.0506 (9)	0.0018 (7)	0.0134 (7)	0.0079 (7)
C23	0.0502 (10)	0.0502 (10)	0.0562 (10)	−0.0067 (8)	0.0115 (8)	0.0060 (8)
C24	0.0557 (12)	0.0652 (13)	0.0798 (14)	−0.0152 (10)	0.0076 (10)	0.0036 (11)
C25	0.0618 (13)	0.0721 (14)	0.0978 (18)	−0.0219 (11)	0.0264 (13)	0.0141 (13)
C26	0.0814 (15)	0.0554 (12)	0.0805 (15)	−0.0124 (11)	0.0400 (13)	0.0132 (11)
C27	0.0641 (11)	0.0369 (9)	0.0573 (11)	0.0010 (8)	0.0227 (9)	0.0107 (7)
C28	0.0898 (15)	0.0540 (11)	0.0460 (10)	0.0008 (10)	0.0212 (10)	0.0144 (8)
C29	0.0851 (15)	0.0614 (12)	0.0419 (10)	−0.0082 (11)	0.0014 (9)	0.0077 (9)
C30	0.0572 (11)	0.0540 (10)	0.0474 (10)	−0.0074 (8)	0.0049 (8)	0.0083 (8)
C31	0.0378 (8)	0.0542 (10)	0.0597 (11)	−0.0030 (7)	0.0165 (8)	0.0017 (8)
C32	0.0726 (13)	0.0447 (10)	0.0697 (13)	−0.0067 (9)	−0.0137 (10)	−0.0104 (9)

O1—C5	1.2175 (19)	C14—C15	1.393 (2)
O2—C20	1.2179 (19)	C14—C19	1.402 (2)
N1—C4	1.456 (2)	C15—C16	1.379 (3)
N1—C31	1.4626 (19)	C15—H15	0.9300
N1—C1	1.4715 (19)	C16—C17	1.379 (3)
N2—C5	1.362 (2)	C16—H16	0.9300
N2—C6	1.401 (2)	C17—C18	1.376 (3)
N2—C32	1.450 (2)	C17—H17	0.9300
C1—C11	1.523 (2)	C18—C19	1.401 (2)
C1—C5	1.561 (2)	C18—H18	0.9300
C1—C2	1.585 (2)	C19—C20	1.487 (2)
C2—C12	1.539 (2)	C21—C30	1.369 (2)
C2—C20	1.544 (2)	C21—C22	1.439 (2)
C2—C3	1.584 (2)	C22—C23	1.418 (2)
C3—C21	1.519 (2)	C22—C27	1.429 (2)
C3—C4	1.534 (2)	C23—C24	1.370 (3)
C3—H3	0.9800	C23—H23	0.9300
C4—H4A	0.9700	C24—C25	1.401 (3)
C4—H4B	0.9700	C24—H24	0.9300
C6—C7	1.381 (2)	C25—C26	1.351 (3)
C6—C11	1.396 (2)	C25—H25	0.9300
C7—C8	1.390 (3)	C26—C27	1.413 (3)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.378 (3)	C27—C28	1.409 (3)
C8—H8	0.9300	C28—C29	1.349 (3)
C9—C10	1.394 (2)	C28—H28	0.9300
C9—H9	0.9300	C29—C30	1.411 (3)
C10—C11	1.375 (2)	C29—H29	0.9300
C10—H10	0.9300	C30—H30	0.9300
C12—C13	1.522 (2)	C31—H31A	0.9600
C12—H12A	0.9700	C31—H31B	0.9600
C12—H12B	0.9700	C31—H31C	0.9600
C13—C14	1.500 (2)	C32—H32A	0.9600
C13—H13A	0.9700	C32—H32B	0.9600
C13—H13B	0.9700	C32—H32C	0.9600
C4—N1—C31	113.04 (13)	C15—C14—C19	118.54 (16)
C4—N1—C1	106.63 (11)	C15—C14—C13	120.75 (16)
C31—N1—C1	115.21 (13)	C19—C14—C13	120.70 (14)
C5—N2—C6	111.54 (13)	C16—C15—C14	120.73 (19)
C5—N2—C32	122.92 (15)	C16—C15—H15	119.6
C6—N2—C32	125.49 (15)	C14—C15—H15	119.6
N1—C1—C11	111.27 (12)	C15—C16—C17	120.67 (18)
N1—C1—C5	111.46 (12)	C15—C16—H16	119.7
C11—C1—C5	101.04 (12)	C17—C16—H16	119.7
N1—C1—C2	101.98 (11)	C18—C17—C16	119.80 (18)
C11—C1—C2	120.09 (12)	C18—C17—H17	120.1
C5—C1—C2	111.26 (11)	C16—C17—H17	120.1
C12—C2—C20	108.06 (12)	C17—C18—C19	120.30 (19)
C12—C2—C3	114.61 (12)	C17—C18—H18	119.8
C20—C2—C3	109.09 (12)	C19—C18—H18	119.8
C12—C2—C1	113.80 (12)	C18—C19—C14	119.92 (16)
C20—C2—C1	107.81 (11)	C18—C19—C20	118.39 (15)
C3—C2—C1	103.18 (11)	C14—C19—C20	121.69 (14)
C21—C3—C4	115.86 (13)	O2—C20—C19	120.29 (14)
C21—C3—C2	115.60 (12)	O2—C20—C2	121.28 (14)
C4—C3—C2	105.14 (12)	C19—C20—C2	118.42 (13)
C21—C3—H3	106.5	C30—C21—C22	118.29 (15)
C4—C3—H3	106.5	C30—C21—C3	122.29 (15)
C2—C3—H3	106.5	C22—C21—C3	119.42 (14)
N1—C4—C3	104.12 (12)	C23—C22—C27	117.62 (16)
N1—C4—H4A	110.9	C23—C22—C21	123.62 (15)
C3—C4—H4A	110.9	C27—C22—C21	118.73 (16)
N1—C4—H4B	110.9	C24—C23—C22	121.23 (18)
C3—C4—H4B	110.9	C24—C23—H23	119.4
H4A—C4—H4B	109.0	C22—C23—H23	119.4
O1—C5—N2	124.73 (15)	C23—C24—C25	120.4 (2)
O1—C5—C1	126.79 (14)	C23—C24—H24	119.8
N2—C5—C1	108.42 (13)	C25—C24—H24	119.8
C7—C6—C11	122.27 (16)	C26—C25—C24	120.1 (2)
C7—C6—N2	127.64 (15)	C26—C25—H25	119.9
C11—C6—N2	110.07 (13)	C24—C25—H25	119.9
C6—C7—C8	117.45 (16)	C25—C26—C27	121.5 (2)
C6—C7—H7	121.3	C25—C26—H26	119.2
C8—C7—H7	121.3	C27—C26—H26	119.2
C9—C8—C7	121.21 (16)	C28—C27—C26	121.06 (18)
C9—C8—H8	119.4	C28—C27—C22	119.87 (17)
C7—C8—H8	119.4	C26—C27—C22	119.06 (19)
C8—C9—C10	120.45 (17)	C29—C28—C27	120.49 (17)
C8—C9—H9	119.8	C29—C28—H28	119.8
C10—C9—H9	119.8	C27—C28—H28	119.8
C11—C10—C9	119.44 (16)	C28—C29—C30	120.26 (19)
C11—C10—H10	120.3	C28—C29—H29	119.9
C9—C10—H10	120.3	C30—C29—H29	119.9
C10—C11—C6	119.16 (15)	C21—C30—C29	122.34 (18)
C10—C11—C1	131.76 (14)	C21—C30—H30	118.8
C6—C11—C1	108.89 (13)	C29—C30—H30	118.8
C13—C12—C2	112.84 (12)	N1—C31—H31A	109.5
C13—C12—H12A	109.0	N1—C31—H31B	109.5
C2—C12—H12A	109.0	H31A—C31—H31B	109.5
C13—C12—H12B	109.0	N1—C31—H31C	109.5
C2—C12—H12B	109.0	H31A—C31—H31C	109.5
H12A—C12—H12B	107.8	H31B—C31—H31C	109.5
C14—C13—C12	111.68 (13)	N2—C32—H32A	109.5
C14—C13—H13A	109.3	N2—C32—H32B	109.5
C12—C13—H13A	109.3	H32A—C32—H32B	109.5
C14—C13—H13B	109.3	N2—C32—H32C	109.5
C12—C13—H13B	109.3	H32A—C32—H32C	109.5
H13A—C13—H13B	107.9	H32B—C32—H32C	109.5
C4—N1—C1—C11	172.75 (12)	C5—C1—C11—C6	−1.96 (15)
C31—N1—C1—C11	−60.95 (17)	C2—C1—C11—C6	−124.64 (14)
C4—N1—C1—C5	−75.29 (15)	C20—C2—C12—C13	57.40 (16)
C31—N1—C1—C5	51.01 (17)	C3—C2—C12—C13	179.26 (12)
C4—N1—C1—C2	43.50 (14)	C1—C2—C12—C13	−62.30 (17)
C31—N1—C1—C2	169.80 (12)	C2—C12—C13—C14	−54.08 (17)
N1—C1—C2—C12	−151.75 (12)	C12—C13—C14—C15	−156.85 (15)
C11—C1—C2—C12	84.77 (16)	C12—C13—C14—C19	21.9 (2)
C5—C1—C2—C12	−32.81 (17)	C19—C14—C15—C16	−1.1 (3)
N1—C1—C2—C20	88.40 (13)	C13—C14—C15—C16	177.67 (17)
C11—C1—C2—C20	−35.07 (17)	C14—C15—C16—C17	−0.7 (3)
C5—C1—C2—C20	−152.65 (12)	C15—C16—C17—C18	1.6 (3)
N1—C1—C2—C3	−26.95 (13)	C16—C17—C18—C19	−0.7 (3)
C11—C1—C2—C3	−150.43 (13)	C17—C18—C19—C14	−1.1 (2)
C5—C1—C2—C3	91.99 (13)	C17—C18—C19—C20	177.82 (16)
C12—C2—C3—C21	−1.88 (18)	C15—C14—C19—C18	2.0 (2)
C20—C2—C3—C21	119.41 (14)	C13—C14—C19—C18	−176.80 (14)
C1—C2—C3—C21	−126.16 (13)	C15—C14—C19—C20	−176.92 (14)
C12—C2—C3—C4	127.22 (14)	C13—C14—C19—C20	4.3 (2)
C20—C2—C3—C4	−111.49 (13)	C18—C19—C20—O2	1.8 (2)
C1—C2—C3—C4	2.94 (15)	C14—C19—C20—O2	−179.27 (14)
C31—N1—C4—C3	−169.85 (13)	C18—C19—C20—C2	−178.04 (13)
C1—N1—C4—C3	−42.26 (16)	C14—C19—C20—C2	0.9 (2)
C21—C3—C4—N1	151.51 (13)	C12—C2—C20—O2	149.50 (14)
C2—C3—C4—N1	22.57 (16)	C3—C2—C20—O2	24.30 (19)
C6—N2—C5—O1	−178.51 (15)	C1—C2—C20—O2	−87.09 (17)
C32—N2—C5—O1	−1.1 (3)	C12—C2—C20—C19	−30.67 (17)
C6—N2—C5—C1	−1.40 (17)	C3—C2—C20—C19	−155.87 (13)
C32—N2—C5—C1	176.01 (15)	C1—C2—C20—C19	92.74 (15)
N1—C1—C5—O1	60.76 (19)	C4—C3—C21—C30	−28.9 (2)
C11—C1—C5—O1	179.05 (15)	C2—C3—C21—C30	94.74 (19)
C2—C1—C5—O1	−52.3 (2)	C4—C3—C21—C22	152.08 (14)
N1—C1—C5—N2	−116.28 (14)	C2—C3—C21—C22	−84.27 (18)
C11—C1—C5—N2	2.01 (15)	C30—C21—C22—C23	−179.50 (16)
C2—C1—C5—N2	130.63 (13)	C3—C21—C22—C23	−0.4 (2)
C5—N2—C6—C7	178.27 (17)	C30—C21—C22—C27	−1.3 (2)
C32—N2—C6—C7	1.0 (3)	C3—C21—C22—C27	177.77 (14)
C5—N2—C6—C11	0.08 (18)	C27—C22—C23—C24	−0.2 (3)
C32—N2—C6—C11	−177.24 (16)	C21—C22—C23—C24	178.00 (18)
C11—C6—C7—C8	0.8 (3)	C22—C23—C24—C25	−0.6 (3)
N2—C6—C7—C8	−177.22 (16)	C23—C24—C25—C26	0.9 (4)
C6—C7—C8—C9	0.1 (3)	C24—C25—C26—C27	−0.4 (4)
C7—C8—C9—C10	−0.3 (3)	C25—C26—C27—C28	−178.8 (2)
C8—C9—C10—C11	−0.4 (3)	C25—C26—C27—C22	−0.4 (3)
C9—C10—C11—C6	1.2 (2)	C23—C22—C27—C28	179.18 (16)
C9—C10—C11—C1	175.58 (15)	C21—C22—C27—C28	0.9 (2)
C7—C6—C11—C10	−1.4 (2)	C23—C22—C27—C26	0.7 (3)
N2—C6—C11—C10	176.88 (14)	C21—C22—C27—C26	−177.61 (16)
C7—C6—C11—C1	−177.00 (15)	C26—C27—C28—C29	178.6 (2)
N2—C6—C11—C1	1.31 (17)	C22—C27—C28—C29	0.1 (3)
N1—C1—C11—C10	−58.3 (2)	C27—C28—C29—C30	−0.7 (3)
C5—C1—C11—C10	−176.78 (16)	C22—C21—C30—C29	0.8 (3)
C2—C1—C11—C10	60.5 (2)	C3—C21—C30—C29	−178.26 (17)
N1—C1—C11—C6	116.47 (14)	C28—C29—C30—C21	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.98	2.25	2.783 (2)	113
C4—H4B···O1	0.97	2.49	3.045 (2)	116
C12—H12A···O1	0.97	2.48	3.143 (2)	126
C32—H32A···O1	0.96	2.52	2.852 (2)	100
C13—H13B···O1i	0.97	2.58	3.482 (2)	156
C32—H32A···O1ii	0.96	2.59	3.364 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1	0.97	2.48	3.143 (2)	126
C13—H13B⋯O1i	0.97	2.58	3.482 (2)	156
C32—H32A⋯O1ii	0.96	2.59	3.364 (2)	138

Symmetry codes: (i) ; (ii) .