1'-Methyl-4'-(1-naphth-yl)-1'',2'',3'',4''-tetra-hydro-indane-2-spiro-2'-pyrrolidine-3'-spiro-2''-naphthalene-1,3,1''-trione.

In the title compound, C(32)H(25)NO(3), 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 indanedione unit is oriented at an angle of 58.9 (1)° with respect to the naphthyl ring system. Three intra-molecular C-H⋯O close contacts and an intra-molecular C-H⋯π inter-action are observed. In the crystal, mol-ecules associate via C-H⋯O hydrogen bonds, forming a helical chain with a C(10) motif along the b axis.

Related literature

For general background to pyrrolidine derivatives, see: Bello et al. (2010 ▶); Pettersson et al. (2011 ▶). For related structures, see: Abdul Ajees et al. (2002 ▶); Selvanayagam et al. (2005 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C32H25NO3

M = 471.53

Orthorhombic,

a = 10.8442 (9) Å

b = 11.431 (1) Å

c = 19.2701 (16) Å

V = 2388.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

28122 measured reflections

3233 independent reflections

2941 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.10

3233 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 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/S1600536811004880/ng5116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004880/ng5116Isup2.hkl

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

C32H25NO3	F(000) = 992
Mr = 471.53	Dx = 1.311 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18128 reflections
a = 10.8442 (9) Å	θ = 2.2–27.7°
b = 11.431 (1) Å	µ = 0.08 mm−1
c = 19.2701 (16) Å	T = 292 K
V = 2388.7 (3) Å3	Block, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Bruker SMART APEX CCD area-detector diffractometer	2941 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 28.0°, θmin = 2.1°
ω scans	h = −14→14
28122 measured reflections	k = −15→14
3233 independent reflections	l = −24→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0796P)2 + 0.0432P] where P = (Fo2 + 2Fc2)/3
3233 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.16 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	0.39079 (16)	0.65842 (13)	0.26515 (8)	0.0626 (4)
O2	0.27742 (18)	1.00671 (13)	0.15142 (9)	0.0670 (4)
O3	0.19107 (14)	0.83352 (13)	0.03036 (7)	0.0548 (4)
N1	0.42985 (14)	0.79880 (14)	0.13310 (8)	0.0437 (3)
C1	0.32344 (15)	0.80317 (14)	0.17897 (8)	0.0373 (3)
C2	0.22397 (15)	0.73033 (13)	0.13771 (8)	0.0344 (3)
C3	0.30573 (15)	0.64431 (14)	0.09301 (8)	0.0379 (3)
H3	0.2908	0.6644	0.0443	0.045*
C4	0.43936 (17)	0.67881 (18)	0.10855 (11)	0.0500 (4)
H4A	0.4747	0.6285	0.1439	0.060*
H4B	0.4897	0.6743	0.0670	0.060*
C5	0.34951 (17)	0.75451 (17)	0.25266 (9)	0.0453 (4)
C6	0.32235 (18)	0.8468 (2)	0.30327 (9)	0.0526 (5)
C7	0.3266 (2)	0.8410 (3)	0.37595 (11)	0.0731 (7)
H7	0.3516	0.7735	0.3989	0.088*
C8	0.2919 (3)	0.9403 (4)	0.41183 (14)	0.0961 (12)
H8	0.2931	0.9388	0.4601	0.115*
C9	0.2557 (3)	1.0410 (4)	0.37891 (19)	0.0943 (11)
H9	0.2323	1.1056	0.4051	0.113*
C10	0.2536 (2)	1.0476 (2)	0.30753 (15)	0.0730 (7)
H10	0.2307	1.1161	0.2849	0.088*
C11	0.28692 (19)	0.94840 (19)	0.27055 (11)	0.0530 (5)
C12	0.29105 (18)	0.93236 (16)	0.19442 (10)	0.0463 (4)
C13	0.12866 (17)	0.66910 (15)	0.18410 (9)	0.0412 (4)
H13A	0.0767	0.6198	0.1554	0.049*
H13B	0.1716	0.6188	0.2166	0.049*
C14	0.04745 (18)	0.75315 (19)	0.22442 (9)	0.0474 (4)
H14A	−0.0166	0.7092	0.2480	0.057*
H14B	0.0968	0.7921	0.2595	0.057*
C15	−0.01132 (16)	0.84350 (17)	0.17879 (9)	0.0451 (4)
C16	−0.1179 (2)	0.90178 (19)	0.19927 (13)	0.0607 (6)
H16	−0.1524	0.8854	0.2424	0.073*
C17	−0.17298 (18)	0.9832 (2)	0.15681 (15)	0.0664 (6)
H17	−0.2446	1.0208	0.1713	0.080*
C18	−0.1227 (2)	1.0096 (2)	0.09295 (15)	0.0639 (6)
H18	−0.1602	1.0648	0.0644	0.077*
C19	−0.01693 (18)	0.95372 (18)	0.07168 (11)	0.0517 (4)
H19	0.0173	0.9716	0.0287	0.062*
C20	0.03943 (16)	0.87038 (16)	0.11414 (9)	0.0417 (4)
C21	0.15470 (15)	0.81437 (15)	0.08854 (8)	0.0379 (3)
C22	0.27640 (16)	0.51479 (15)	0.10044 (9)	0.0392 (3)
C23	0.17262 (16)	0.46728 (15)	0.06386 (8)	0.0394 (3)
C24	0.09433 (18)	0.53423 (18)	0.02056 (10)	0.0481 (4)
H24	0.1111	0.6134	0.0144	0.058*
C25	−0.0049 (2)	0.4864 (2)	−0.01248 (12)	0.0605 (5)
H25	−0.0552	0.5332	−0.0400	0.073*
C26	−0.0314 (2)	0.3677 (2)	−0.00510 (14)	0.0702 (6)
H26	−0.0985	0.3352	−0.0281	0.084*
C27	0.0406 (2)	0.3001 (2)	0.03549 (13)	0.0656 (6)
H27	0.0218	0.2211	0.0401	0.079*
C28	0.1443 (2)	0.34598 (15)	0.07131 (10)	0.0480 (4)
C29	0.2201 (2)	0.27509 (17)	0.11260 (11)	0.0577 (5)
H29	0.2024	0.1958	0.1169	0.069*
C30	0.3187 (2)	0.32053 (19)	0.14624 (12)	0.0600 (5)
H30	0.3686	0.2725	0.1732	0.072*
C31	0.34582 (19)	0.44138 (18)	0.14031 (10)	0.0509 (4)
H31	0.4130	0.4716	0.1644	0.061*
C32	0.54458 (19)	0.8442 (2)	0.16095 (12)	0.0592 (5)
H32A	0.5318	0.9224	0.1777	0.089*
H32B	0.6061	0.8450	0.1251	0.089*
H32C	0.5718	0.7954	0.1985	0.089*

	U11	U22	U33	U12	U13	U23
O1	0.0718 (9)	0.0584 (8)	0.0577 (8)	0.0018 (8)	−0.0114 (7)	0.0189 (7)
O2	0.0855 (12)	0.0406 (7)	0.0750 (10)	0.0010 (8)	−0.0074 (9)	0.0104 (7)
O3	0.0616 (8)	0.0629 (8)	0.0400 (6)	0.0169 (7)	0.0096 (6)	0.0150 (6)
N1	0.0374 (7)	0.0486 (8)	0.0451 (7)	−0.0078 (6)	0.0025 (6)	0.0002 (7)
C1	0.0399 (8)	0.0374 (8)	0.0346 (7)	−0.0028 (7)	−0.0015 (6)	0.0035 (6)
C2	0.0358 (7)	0.0346 (7)	0.0327 (7)	−0.0020 (6)	0.0013 (6)	0.0028 (6)
C3	0.0376 (8)	0.0387 (8)	0.0373 (7)	0.0012 (6)	0.0013 (6)	−0.0007 (6)
C4	0.0375 (8)	0.0540 (10)	0.0584 (10)	−0.0019 (8)	0.0070 (8)	−0.0072 (9)
C5	0.0437 (9)	0.0532 (10)	0.0391 (8)	−0.0092 (8)	−0.0046 (7)	0.0081 (7)
C6	0.0436 (9)	0.0732 (13)	0.0409 (8)	−0.0159 (9)	−0.0009 (7)	−0.0064 (9)
C7	0.0628 (13)	0.115 (2)	0.0416 (9)	−0.0265 (14)	−0.0014 (9)	−0.0075 (12)
C8	0.0746 (17)	0.162 (3)	0.0520 (13)	−0.036 (2)	0.0115 (13)	−0.0458 (19)
C9	0.0712 (17)	0.124 (3)	0.0873 (19)	−0.0207 (19)	0.0137 (15)	−0.062 (2)
C10	0.0568 (12)	0.0728 (14)	0.0895 (17)	−0.0096 (12)	0.0046 (12)	−0.0365 (14)
C11	0.0445 (9)	0.0590 (11)	0.0554 (10)	−0.0092 (9)	0.0025 (8)	−0.0154 (9)
C12	0.0448 (9)	0.0405 (8)	0.0535 (9)	−0.0047 (8)	−0.0013 (8)	−0.0034 (8)
C13	0.0425 (8)	0.0435 (8)	0.0377 (7)	−0.0075 (7)	0.0048 (7)	0.0055 (7)
C14	0.0445 (8)	0.0577 (10)	0.0399 (8)	−0.0105 (8)	0.0119 (7)	−0.0032 (8)
C15	0.0366 (8)	0.0483 (9)	0.0505 (9)	−0.0072 (7)	0.0051 (7)	−0.0137 (8)
C16	0.0459 (10)	0.0619 (12)	0.0744 (14)	−0.0072 (9)	0.0156 (10)	−0.0261 (11)
C17	0.0381 (9)	0.0605 (12)	0.1007 (17)	0.0060 (9)	0.0001 (11)	−0.0292 (13)
C18	0.0488 (10)	0.0517 (11)	0.0913 (17)	0.0112 (9)	−0.0177 (11)	−0.0161 (11)
C19	0.0484 (10)	0.0489 (10)	0.0577 (10)	0.0064 (8)	−0.0114 (8)	−0.0061 (9)
C20	0.0362 (8)	0.0430 (8)	0.0459 (8)	0.0014 (7)	−0.0026 (7)	−0.0069 (7)
C21	0.0363 (7)	0.0403 (8)	0.0370 (7)	0.0020 (7)	0.0021 (6)	0.0024 (6)
C22	0.0406 (8)	0.0386 (8)	0.0383 (7)	0.0046 (7)	0.0025 (7)	−0.0006 (6)
C23	0.0432 (8)	0.0371 (8)	0.0379 (7)	0.0018 (7)	0.0034 (7)	−0.0026 (6)
C24	0.0519 (10)	0.0474 (9)	0.0449 (9)	−0.0006 (8)	−0.0057 (8)	0.0011 (7)
C25	0.0532 (11)	0.0731 (14)	0.0551 (11)	−0.0015 (11)	−0.0117 (9)	−0.0020 (11)
C26	0.0621 (13)	0.0746 (15)	0.0740 (15)	−0.0168 (12)	−0.0070 (11)	−0.0181 (13)
C27	0.0706 (14)	0.0475 (10)	0.0789 (14)	−0.0110 (11)	0.0082 (12)	−0.0151 (11)
C28	0.0580 (11)	0.0361 (8)	0.0501 (9)	0.0004 (8)	0.0097 (8)	−0.0059 (7)
C29	0.0759 (14)	0.0347 (8)	0.0625 (11)	0.0090 (9)	0.0135 (11)	0.0012 (8)
C30	0.0762 (14)	0.0471 (10)	0.0566 (11)	0.0250 (10)	0.0023 (11)	0.0087 (9)
C31	0.0531 (10)	0.0507 (10)	0.0488 (10)	0.0124 (9)	−0.0060 (8)	−0.0002 (8)
C32	0.0446 (9)	0.0717 (13)	0.0613 (11)	−0.0167 (10)	−0.0039 (9)	0.0028 (11)

O1—C5	1.210 (3)	C14—H14B	0.9700
O2—C12	1.196 (2)	C15—C16	1.391 (3)
O3—C21	1.208 (2)	C15—C20	1.396 (3)
N1—C32	1.451 (2)	C16—C17	1.376 (4)
N1—C1	1.454 (2)	C16—H16	0.9300
N1—C4	1.455 (3)	C17—C18	1.379 (4)
C1—C12	1.547 (2)	C17—H17	0.9300
C1—C5	1.551 (2)	C18—C19	1.376 (3)
C1—C2	1.578 (2)	C18—H18	0.9300
C2—C13	1.535 (2)	C19—C20	1.397 (3)
C2—C21	1.544 (2)	C19—H19	0.9300
C2—C3	1.580 (2)	C20—C21	1.489 (2)
C3—C22	1.521 (2)	C22—C31	1.364 (3)
C3—C4	1.531 (2)	C22—C23	1.435 (2)
C3—H3	0.9800	C23—C24	1.415 (3)
C4—H4A	0.9700	C23—C28	1.428 (2)
C4—H4B	0.9700	C24—C25	1.365 (3)
C5—C6	1.466 (3)	C24—H24	0.9300
C6—C11	1.376 (3)	C25—C26	1.394 (4)
C6—C7	1.403 (3)	C25—H25	0.9300
C7—C8	1.381 (5)	C26—C27	1.348 (4)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.372 (5)	C27—C28	1.419 (3)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.378 (5)	C28—C29	1.402 (3)
C9—H9	0.9300	C29—C30	1.354 (3)
C10—C11	1.387 (3)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.417 (3)
C11—C12	1.479 (3)	C30—H30	0.9300
C13—C14	1.517 (3)	C31—H31	0.9300
C13—H13A	0.9700	C32—H32A	0.9600
C13—H13B	0.9700	C32—H32B	0.9600
C14—C15	1.499 (3)	C32—H32C	0.9600
C14—H14A	0.9700
C32—N1—C1	116.31 (15)	C15—C14—H14B	109.1
C32—N1—C4	113.40 (16)	C13—C14—H14B	109.1
C1—N1—C4	106.64 (14)	H14A—C14—H14B	107.8
N1—C1—C12	109.27 (14)	C16—C15—C20	118.4 (2)
N1—C1—C5	113.54 (14)	C16—C15—C14	121.12 (18)
C12—C1—C5	101.98 (14)	C20—C15—C14	120.50 (16)
N1—C1—C2	102.60 (12)	C17—C16—C15	121.1 (2)
C12—C1—C2	116.46 (14)	C17—C16—H16	119.5
C5—C1—C2	113.37 (13)	C15—C16—H16	119.5
C13—C2—C21	108.26 (13)	C16—C17—C18	120.4 (2)
C13—C2—C1	114.05 (12)	C16—C17—H17	119.8
C21—C2—C1	108.27 (12)	C18—C17—H17	119.8
C13—C2—C3	114.30 (13)	C19—C18—C17	119.6 (2)
C21—C2—C3	109.00 (12)	C19—C18—H18	120.2
C1—C2—C3	102.69 (12)	C17—C18—H18	120.2
C22—C3—C4	115.47 (15)	C18—C19—C20	120.5 (2)
C22—C3—C2	115.93 (13)	C18—C19—H19	119.8
C4—C3—C2	105.32 (13)	C20—C19—H19	119.8
C22—C3—H3	106.5	C15—C20—C19	120.02 (17)
C4—C3—H3	106.5	C15—C20—C21	122.15 (17)
C2—C3—H3	106.5	C19—C20—C21	117.83 (16)
N1—C4—C3	103.85 (14)	O3—C21—C20	120.24 (16)
N1—C4—H4A	111.0	O3—C21—C2	121.55 (15)
C3—C4—H4A	111.0	C20—C21—C2	118.21 (14)
N1—C4—H4B	111.0	C31—C22—C23	118.48 (17)
C3—C4—H4B	111.0	C31—C22—C3	122.43 (17)
H4A—C4—H4B	109.0	C23—C22—C3	119.09 (15)
O1—C5—C6	126.50 (17)	C24—C23—C28	117.09 (17)
O1—C5—C1	125.10 (17)	C24—C23—C22	123.75 (16)
C6—C5—C1	108.31 (16)	C28—C23—C22	119.15 (16)
C11—C6—C7	120.4 (2)	C25—C24—C23	122.1 (2)
C11—C6—C5	111.01 (16)	C25—C24—H24	118.9
C7—C6—C5	128.6 (2)	C23—C24—H24	118.9
C8—C7—C6	116.9 (3)	C24—C25—C26	120.3 (2)
C8—C7—H7	121.5	C24—C25—H25	119.9
C6—C7—H7	121.5	C26—C25—H25	119.9
C9—C8—C7	122.4 (3)	C27—C26—C25	119.9 (2)
C9—C8—H8	118.8	C27—C26—H26	120.1
C7—C8—H8	118.8	C25—C26—H26	120.1
C8—C9—C10	120.8 (3)	C26—C27—C28	121.9 (2)
C8—C9—H9	119.6	C26—C27—H27	119.0
C10—C9—H9	119.6	C28—C27—H27	119.0
C9—C10—C11	117.7 (3)	C29—C28—C27	121.79 (19)
C9—C10—H10	121.2	C29—C28—C23	119.48 (19)
C11—C10—H10	121.2	C27—C28—C23	118.72 (19)
C6—C11—C10	121.8 (2)	C30—C29—C28	120.87 (18)
C6—C11—C12	109.95 (17)	C30—C29—H29	119.6
C10—C11—C12	128.2 (2)	C28—C29—H29	119.6
O2—C12—C11	126.53 (19)	C29—C30—C31	119.94 (19)
O2—C12—C1	124.96 (17)	C29—C30—H30	120.0
C11—C12—C1	108.43 (16)	C31—C30—H30	120.0
C14—C13—C2	113.59 (14)	C22—C31—C30	122.0 (2)
C14—C13—H13A	108.8	C22—C31—H31	119.0
C2—C13—H13A	108.8	C30—C31—H31	119.0
C14—C13—H13B	108.8	N1—C32—H32A	109.5
C2—C13—H13B	108.8	N1—C32—H32B	109.5
H13A—C13—H13B	107.7	H32A—C32—H32B	109.5
C15—C14—C13	112.50 (14)	N1—C32—H32C	109.5
C15—C14—H14A	109.1	H32A—C32—H32C	109.5
C13—C14—H14A	109.1	H32B—C32—H32C	109.5
C32—N1—C1—C12	64.5 (2)	C5—C1—C12—C11	−5.58 (18)
C4—N1—C1—C12	−167.92 (15)	C2—C1—C12—C11	118.38 (16)
C32—N1—C1—C5	−48.6 (2)	C21—C2—C13—C14	−55.95 (19)
C4—N1—C1—C5	78.99 (18)	C1—C2—C13—C14	64.64 (19)
C32—N1—C1—C2	−171.34 (16)	C3—C2—C13—C14	−177.63 (14)
C4—N1—C1—C2	−43.74 (17)	C2—C13—C14—C15	51.9 (2)
N1—C1—C2—C13	151.52 (14)	C13—C14—C15—C16	157.93 (17)
C12—C1—C2—C13	−89.21 (17)	C13—C14—C15—C20	−21.5 (2)
C5—C1—C2—C13	28.67 (19)	C20—C15—C16—C17	0.6 (3)
N1—C1—C2—C21	−87.90 (15)	C14—C15—C16—C17	−178.84 (18)
C12—C1—C2—C21	31.37 (18)	C15—C16—C17—C18	−0.6 (3)
C5—C1—C2—C21	149.25 (14)	C16—C17—C18—C19	0.1 (3)
N1—C1—C2—C3	27.30 (15)	C17—C18—C19—C20	0.3 (3)
C12—C1—C2—C3	146.57 (14)	C16—C15—C20—C19	−0.2 (3)
C5—C1—C2—C3	−95.55 (15)	C14—C15—C20—C19	179.24 (17)
C13—C2—C3—C22	1.7 (2)	C16—C15—C20—C21	178.65 (16)
C21—C2—C3—C22	−119.53 (15)	C14—C15—C20—C21	−1.9 (3)
C1—C2—C3—C22	125.80 (14)	C18—C19—C20—C15	−0.2 (3)
C13—C2—C3—C4	−127.23 (16)	C18—C19—C20—C21	−179.14 (17)
C21—C2—C3—C4	111.49 (16)	C15—C20—C21—O3	174.69 (18)
C1—C2—C3—C4	−3.18 (16)	C19—C20—C21—O3	−6.4 (3)
C32—N1—C4—C3	171.27 (16)	C15—C20—C21—C2	−4.2 (2)
C1—N1—C4—C3	41.97 (18)	C19—C20—C21—C2	174.68 (16)
C22—C3—C4—N1	−151.38 (14)	C13—C2—C21—O3	−146.97 (17)
C2—C3—C4—N1	−22.13 (18)	C1—C2—C21—O3	88.92 (19)
N1—C1—C5—O1	−54.7 (2)	C3—C2—C21—O3	−22.1 (2)
C12—C1—C5—O1	−172.11 (18)	C13—C2—C21—C20	31.93 (19)
C2—C1—C5—O1	61.9 (2)	C1—C2—C21—C20	−92.19 (16)
N1—C1—C5—C6	122.12 (16)	C3—C2—C21—C20	156.82 (14)
C12—C1—C5—C6	4.71 (18)	C4—C3—C22—C31	22.4 (2)
C2—C1—C5—C6	−121.30 (15)	C2—C3—C22—C31	−101.47 (19)
O1—C5—C6—C11	174.55 (19)	C4—C3—C22—C23	−157.10 (15)
C1—C5—C6—C11	−2.2 (2)	C2—C3—C22—C23	79.05 (19)
O1—C5—C6—C7	−6.6 (3)	C31—C22—C23—C24	−179.52 (17)
C1—C5—C6—C7	176.6 (2)	C3—C22—C23—C24	0.0 (3)
C11—C6—C7—C8	1.1 (3)	C31—C22—C23—C28	1.1 (2)
C5—C6—C7—C8	−177.6 (2)	C3—C22—C23—C28	−179.40 (15)
C6—C7—C8—C9	−0.6 (4)	C28—C23—C24—C25	0.6 (3)
C7—C8—C9—C10	−0.6 (5)	C22—C23—C24—C25	−178.80 (18)
C8—C9—C10—C11	1.3 (4)	C23—C24—C25—C26	−0.9 (3)
C7—C6—C11—C10	−0.5 (3)	C24—C25—C26—C27	0.8 (4)
C5—C6—C11—C10	178.48 (18)	C25—C26—C27—C28	−0.3 (4)
C7—C6—C11—C12	179.53 (19)	C26—C27—C28—C29	−179.0 (2)
C5—C6—C11—C12	−1.5 (2)	C26—C27—C28—C23	−0.1 (3)
C9—C10—C11—C6	−0.7 (4)	C24—C23—C28—C29	178.86 (18)
C9—C10—C11—C12	179.3 (2)	C22—C23—C28—C29	−1.7 (3)
C6—C11—C12—O2	−172.2 (2)	C24—C23—C28—C27	−0.1 (3)
C10—C11—C12—O2	7.8 (4)	C22—C23—C28—C27	179.34 (17)
C6—C11—C12—C1	4.7 (2)	C27—C28—C29—C30	179.9 (2)
C10—C11—C12—C1	−175.3 (2)	C23—C28—C29—C30	0.9 (3)
N1—C1—C12—O2	50.9 (2)	C28—C29—C30—C31	0.4 (3)
C5—C1—C12—O2	171.4 (2)	C23—C22—C31—C30	0.3 (3)
C2—C1—C12—O2	−64.7 (2)	C3—C22—C31—C30	−179.19 (18)
N1—C1—C12—C11	−126.03 (16)	C29—C30—C31—C22	−1.1 (3)

Cg1 is centroid of the C1/C5/C6/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.98	2.23	2.772 (2)	114
C4—H4A···O1	0.97	2.53	3.072 (3)	115
C13—H13B···O1	0.97	2.59	3.246 (3)	125
C29—H29···O2i	0.93	2.40	3.218 (2)	146
C17—H17···O1ii	0.93	2.55	3.442 (3)	163
C14—H14B···Cg1	0.97	2.51	3.146 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is centroid of the C1/C5/C6/C11/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3	0.98	2.23	2.772 (2)	114
C4—H4A⋯O1	0.97	2.53	3.072 (3)	115
C13—H13B⋯O1	0.97	2.59	3.246 (3)	125
C29—H29⋯O2i	0.93	2.40	3.218 (2)	146
C17—H17⋯O1ii	0.93	2.55	3.442 (3)	163
C14—H14B⋯Cg1	0.97	2.51	3.146 (2)	123

Symmetry codes: (i) ; (ii) .