1-(2-Hy-droxy-eth-yl)-1'-methyl-4'-(naph-thal-en-1-yl)-1'',2'',3'',4''-tetra-hydro-dispiro-[indoline-3,2'-pyrrolidine-3',2''-naphthalene]-2,1''-dione.

In the title compound, C(33)H(30)N(2)O(3), the pyrrolidine ring adopts an envelope conformation in which the H atom attached the an ortho-C atom deviates from the plane, whereas the cyclo-hexa-none ring in the tetra-hydro-naphthalene fused-ring system adopts a sofa conformation. The oxindoline ring system is almost perpendicular with respect to the mean plane of the pyrrolidine ring, with a dihedral angle of 89.0 (1)°. Five intra-molecular C-H⋯O close contacts are observed. In the crystal, mol-ecules associate via O-H⋯O hydrogen bonds, forming R(2) (2)(14) dimers. In addition, there are weak C-H⋯π inter-actions.

Related literature

For general background to pyrrolidine derivatives, see: Sundar et al. (2011 ▶); Crooks & Sommerville (1982 ▶); Stylianakis et al. (2003 ▶). For a related structure, see: Selvanayagam, Ravikumar et al. (2011 ▶); Selvanayagam, Sridhar et al. (2011 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C33H30N2O3

M = 502.59

Monoclinic,

a = 12.0236 (18) Å

b = 14.054 (2) Å

c = 15.950 (2) Å

β = 107.796 (2)°

V = 2566.2 (7) 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

29561 measured reflections

6100 independent reflections

4956 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.02

6100 reflections

345 parameters

H-atom parameters constrained

Δρmax = 0.27 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 datablock(s) I, global. DOI: 10.1107/S1600536812006617/bt5819sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006617/bt5819Isup2.hkl

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

C33H30N2O3	F(000) = 1064
Mr = 502.59	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18685 reflections
a = 12.0236 (18) Å	θ = 2.2–27.8°
b = 14.054 (2) Å	µ = 0.08 mm−1
c = 15.950 (2) Å	T = 292 K
β = 107.796 (2)°	Block, colourless
V = 2566.2 (7) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4956 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 28.0°, θmin = 1.8°
ω scans	h = −15→15
29561 measured reflections	k = −18→18
6100 independent reflections	l = −21→20

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0763P)2 + 0.3393P] where P = (Fo2 + 2Fc2)/3
6100 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.27 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
N1	0.10384 (8)	0.22419 (7)	0.19534 (6)	0.0402 (2)
N2	0.00850 (9)	−0.00310 (7)	0.19134 (7)	0.0459 (2)
O1	0.30700 (9)	0.24467 (6)	0.39617 (6)	0.0558 (2)
O2	0.11658 (9)	0.03889 (7)	0.10210 (6)	0.0555 (2)
O3	−0.19054 (11)	0.03227 (8)	0.03809 (7)	0.0652 (3)
H3	−0.1606	0.0206	−0.0006	0.098*
C1	0.19263 (10)	0.24133 (9)	0.15200 (8)	0.0434 (3)
H1A	0.1927	0.3073	0.1341	0.052*
H1B	0.1812	0.2007	0.1009	0.052*
C2	0.30466 (10)	0.21616 (8)	0.22418 (7)	0.0399 (2)
H2	0.3234	0.2710	0.2640	0.048*
C3	0.26925 (9)	0.13307 (7)	0.27700 (7)	0.0365 (2)
C4	0.13143 (10)	0.13071 (8)	0.23768 (7)	0.0369 (2)
C5	−0.01552 (11)	0.23600 (10)	0.13839 (9)	0.0523 (3)
H5A	−0.0279	0.3010	0.1194	0.078*
H5B	−0.0689	0.2195	0.1702	0.078*
H5C	−0.0286	0.1953	0.0880	0.078*
C6	0.41155 (11)	0.19724 (9)	0.19625 (8)	0.0449 (3)
C7	0.40481 (14)	0.14455 (11)	0.12339 (10)	0.0597 (4)
H7	0.3324	0.1218	0.0894	0.072*
C8	0.50454 (17)	0.12346 (14)	0.09794 (12)	0.0758 (5)
H8	0.4970	0.0891	0.0467	0.091*
C9	0.61114 (15)	0.15324 (14)	0.14808 (13)	0.0746 (5)
H9	0.6767	0.1379	0.1315	0.090*
C10	0.62429 (12)	0.20652 (11)	0.22432 (11)	0.0603 (4)
C11	0.73543 (14)	0.23652 (14)	0.27924 (15)	0.0771 (5)
H11	0.8019	0.2193	0.2646	0.093*
C12	0.74729 (15)	0.28936 (15)	0.35201 (15)	0.0834 (6)
H12	0.8212	0.3078	0.3870	0.100*
C13	0.65024 (15)	0.31585 (13)	0.37427 (13)	0.0769 (5)
H13	0.6588	0.3537	0.4237	0.092*
C14	0.54088 (13)	0.28741 (10)	0.32481 (10)	0.0588 (4)
H14	0.4766	0.3055	0.3419	0.071*
C15	0.52372 (11)	0.23149 (9)	0.24881 (9)	0.0480 (3)
C16	0.30264 (10)	0.16184 (8)	0.37488 (7)	0.0397 (2)
C17	0.32705 (10)	0.08631 (9)	0.44286 (7)	0.0412 (3)
C18	0.35333 (11)	0.11383 (10)	0.53084 (8)	0.0496 (3)
H18	0.3584	0.1781	0.5453	0.060*
C19	0.37171 (13)	0.04706 (12)	0.59598 (9)	0.0601 (4)
H19	0.3896	0.0658	0.6545	0.072*
C20	0.36361 (13)	−0.04786 (12)	0.57435 (10)	0.0643 (4)
H20	0.3742	−0.0934	0.6184	0.077*
C21	0.34002 (13)	−0.07620 (10)	0.48835 (10)	0.0574 (3)
H21	0.3363	−0.1407	0.4749	0.069*
C22	0.32156 (10)	−0.00945 (9)	0.42105 (8)	0.0445 (3)
C23	0.29843 (12)	−0.03946 (8)	0.32751 (9)	0.0494 (3)
H23A	0.2166	−0.0560	0.3029	0.059*
H23B	0.3442	−0.0958	0.3256	0.059*
C24	0.32839 (11)	0.03774 (8)	0.27179 (8)	0.0433 (3)
H24A	0.3053	0.0168	0.2109	0.052*
H24B	0.4124	0.0469	0.2907	0.052*
C25	0.06134 (10)	0.10957 (8)	0.29967 (7)	0.0388 (2)
C26	0.05570 (11)	0.15438 (9)	0.37485 (8)	0.0462 (3)
H26	0.0992	0.2090	0.3950	0.055*
C27	−0.01597 (13)	0.11681 (11)	0.42021 (9)	0.0578 (4)
H27	−0.0198	0.1463	0.4715	0.069*
C28	−0.08122 (13)	0.03680 (13)	0.39040 (10)	0.0634 (4)
H28	−0.1276	0.0121	0.4224	0.076*
C29	−0.07937 (12)	−0.00782 (11)	0.31387 (9)	0.0574 (3)
H29	−0.1248	−0.0614	0.2929	0.069*
C30	−0.00761 (10)	0.03006 (8)	0.26956 (8)	0.0435 (3)
C31	0.08823 (10)	0.05013 (8)	0.16833 (8)	0.0420 (3)
C32	−0.05995 (13)	−0.07827 (10)	0.13719 (10)	0.0569 (3)
H32A	−0.0609	−0.1330	0.1740	0.068*
H32B	−0.0230	−0.0974	0.0936	0.068*
C33	−0.18359 (13)	−0.04818 (11)	0.09099 (10)	0.0604 (4)
H33A	−0.2245	−0.1003	0.0547	0.072*
H33B	−0.2227	−0.0349	0.1347	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0400 (5)	0.0397 (5)	0.0409 (5)	0.0025 (4)	0.0125 (4)	0.0074 (4)
N2	0.0489 (6)	0.0408 (5)	0.0435 (5)	−0.0068 (4)	0.0073 (4)	−0.0023 (4)
O1	0.0814 (7)	0.0387 (5)	0.0462 (5)	−0.0043 (4)	0.0181 (5)	−0.0082 (4)
O2	0.0625 (6)	0.0640 (6)	0.0414 (5)	−0.0040 (4)	0.0178 (4)	−0.0132 (4)
O3	0.0724 (7)	0.0672 (6)	0.0546 (6)	0.0100 (5)	0.0171 (5)	0.0018 (5)
C1	0.0446 (6)	0.0444 (6)	0.0425 (6)	0.0008 (5)	0.0152 (5)	0.0075 (5)
C2	0.0406 (6)	0.0385 (6)	0.0409 (6)	−0.0016 (4)	0.0131 (5)	0.0007 (4)
C3	0.0405 (6)	0.0340 (5)	0.0346 (5)	0.0005 (4)	0.0106 (4)	−0.0017 (4)
C4	0.0413 (6)	0.0353 (5)	0.0341 (5)	−0.0008 (4)	0.0113 (4)	0.0003 (4)
C5	0.0432 (7)	0.0575 (8)	0.0532 (7)	0.0032 (5)	0.0103 (5)	0.0145 (6)
C6	0.0449 (6)	0.0457 (6)	0.0461 (6)	0.0018 (5)	0.0170 (5)	0.0061 (5)
C7	0.0603 (8)	0.0694 (9)	0.0528 (7)	0.0048 (7)	0.0223 (6)	−0.0030 (6)
C8	0.0860 (12)	0.0850 (12)	0.0696 (10)	0.0159 (9)	0.0435 (9)	−0.0009 (9)
C9	0.0644 (10)	0.0850 (11)	0.0888 (12)	0.0199 (8)	0.0447 (9)	0.0227 (10)
C10	0.0489 (7)	0.0606 (8)	0.0762 (10)	0.0076 (6)	0.0264 (7)	0.0291 (7)
C11	0.0430 (8)	0.0840 (12)	0.1049 (14)	0.0056 (7)	0.0236 (8)	0.0441 (11)
C12	0.0495 (9)	0.0860 (13)	0.1007 (15)	−0.0155 (8)	0.0022 (9)	0.0262 (11)
C13	0.0629 (10)	0.0701 (10)	0.0830 (11)	−0.0189 (8)	0.0007 (8)	0.0044 (9)
C14	0.0500 (7)	0.0546 (8)	0.0660 (9)	−0.0086 (6)	0.0090 (6)	0.0026 (6)
C15	0.0430 (6)	0.0447 (6)	0.0568 (7)	0.0013 (5)	0.0159 (5)	0.0167 (5)
C16	0.0415 (6)	0.0378 (6)	0.0387 (5)	−0.0004 (4)	0.0104 (4)	−0.0034 (4)
C17	0.0386 (6)	0.0454 (6)	0.0377 (5)	0.0024 (5)	0.0088 (4)	0.0012 (5)
C18	0.0482 (7)	0.0594 (8)	0.0405 (6)	0.0038 (6)	0.0125 (5)	−0.0024 (5)
C19	0.0564 (8)	0.0838 (11)	0.0390 (6)	0.0105 (7)	0.0133 (6)	0.0085 (6)
C20	0.0606 (9)	0.0761 (10)	0.0555 (8)	0.0123 (7)	0.0167 (7)	0.0265 (7)
C21	0.0583 (8)	0.0502 (7)	0.0614 (8)	0.0060 (6)	0.0149 (6)	0.0141 (6)
C22	0.0409 (6)	0.0430 (6)	0.0469 (6)	0.0035 (5)	0.0093 (5)	0.0056 (5)
C23	0.0580 (7)	0.0339 (6)	0.0504 (7)	0.0049 (5)	0.0080 (6)	−0.0015 (5)
C24	0.0481 (6)	0.0388 (6)	0.0409 (6)	0.0058 (5)	0.0104 (5)	−0.0050 (4)
C25	0.0412 (6)	0.0378 (5)	0.0373 (5)	0.0030 (4)	0.0119 (4)	0.0058 (4)
C26	0.0499 (7)	0.0474 (6)	0.0417 (6)	0.0076 (5)	0.0147 (5)	0.0030 (5)
C27	0.0603 (8)	0.0749 (10)	0.0432 (7)	0.0141 (7)	0.0234 (6)	0.0107 (6)
C28	0.0541 (8)	0.0854 (11)	0.0550 (8)	0.0013 (7)	0.0229 (6)	0.0247 (7)
C29	0.0529 (7)	0.0608 (8)	0.0564 (8)	−0.0097 (6)	0.0134 (6)	0.0168 (6)
C30	0.0434 (6)	0.0431 (6)	0.0414 (6)	−0.0001 (5)	0.0092 (5)	0.0085 (5)
C31	0.0429 (6)	0.0414 (6)	0.0386 (6)	−0.0001 (5)	0.0079 (5)	−0.0026 (4)
C32	0.0621 (8)	0.0406 (7)	0.0592 (8)	−0.0100 (6)	0.0053 (6)	−0.0056 (6)
C33	0.0583 (8)	0.0640 (9)	0.0517 (7)	−0.0152 (6)	0.0063 (6)	−0.0021 (6)

N1—C5	1.4545 (16)	C12—H12	0.9300
N1—C1	1.4582 (15)	C13—C14	1.370 (2)
N1—C4	1.4681 (14)	C13—H13	0.9300
N2—C31	1.3522 (16)	C14—C15	1.406 (2)
N2—C30	1.3996 (16)	C14—H14	0.9300
N2—C32	1.4508 (16)	C16—C17	1.4812 (16)
O1—C16	1.2091 (14)	C17—C22	1.3865 (17)
O2—C31	1.2154 (15)	C17—C18	1.3957 (16)
O3—C33	1.3979 (18)	C18—C19	1.3669 (19)
O3—H3	0.8200	C18—H18	0.9300
C1—C2	1.5222 (16)	C19—C20	1.374 (2)
C1—H1A	0.9700	C19—H19	0.9300
C1—H1B	0.9700	C20—C21	1.372 (2)
C2—C6	1.5069 (17)	C20—H20	0.9300
C2—C3	1.5729 (15)	C21—C22	1.3914 (18)
C2—H2	0.9800	C21—H21	0.9300
C3—C24	1.5308 (15)	C22—C23	1.4926 (18)
C3—C16	1.5423 (15)	C23—C24	1.5142 (18)
C3—C4	1.5828 (16)	C23—H23A	0.9700
C4—C25	1.5118 (15)	C23—H23B	0.9700
C4—C31	1.5572 (15)	C24—H24A	0.9700
C5—H5A	0.9600	C24—H24B	0.9700
C5—H5B	0.9600	C25—C26	1.3743 (17)
C5—H5C	0.9600	C25—C30	1.3868 (17)
C6—C7	1.3593 (19)	C26—C27	1.3876 (19)
C6—C15	1.4361 (18)	C26—H26	0.9300
C7—C8	1.410 (2)	C27—C28	1.370 (2)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.353 (3)	C28—C29	1.378 (2)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.395 (3)	C29—C30	1.3784 (18)
C9—H9	0.9300	C29—H29	0.9300
C10—C11	1.420 (2)	C32—C33	1.504 (2)
C10—C15	1.4236 (19)	C32—H32A	0.9700
C11—C12	1.348 (3)	C32—H32B	0.9700
C11—H11	0.9300	C33—H33A	0.9700
C12—C13	1.371 (3)	C33—H33B	0.9700
C5—N1—C1	114.25 (9)	O1—C16—C17	120.16 (10)
C5—N1—C4	115.50 (9)	O1—C16—C3	120.81 (10)
C1—N1—C4	105.70 (9)	C17—C16—C3	119.02 (9)
C31—N2—C30	111.13 (10)	C22—C17—C18	120.00 (11)
C31—N2—C32	124.16 (11)	C22—C17—C16	121.90 (10)
C30—N2—C32	124.42 (11)	C18—C17—C16	118.09 (11)
C33—O3—H3	109.5	C19—C18—C17	120.55 (13)
N1—C1—C2	102.12 (9)	C19—C18—H18	119.7
N1—C1—H1A	111.3	C17—C18—H18	119.7
C2—C1—H1A	111.3	C18—C19—C20	119.55 (13)
N1—C1—H1B	111.3	C18—C19—H19	120.2
C2—C1—H1B	111.3	C20—C19—H19	120.2
H1A—C1—H1B	109.2	C21—C20—C19	120.66 (13)
C6—C2—C1	117.06 (10)	C21—C20—H20	119.7
C6—C2—C3	114.98 (9)	C19—C20—H20	119.7
C1—C2—C3	104.82 (9)	C20—C21—C22	120.73 (14)
C6—C2—H2	106.4	C20—C21—H21	119.6
C1—C2—H2	106.4	C22—C21—H21	119.6
C3—C2—H2	106.4	C17—C22—C21	118.48 (12)
C24—C3—C16	107.63 (9)	C17—C22—C23	120.34 (11)
C24—C3—C2	114.47 (9)	C21—C22—C23	121.17 (12)
C16—C3—C2	108.55 (9)	C22—C23—C24	112.28 (10)
C24—C3—C4	114.06 (9)	C22—C23—H23A	109.1
C16—C3—C4	108.89 (9)	C24—C23—H23A	109.1
C2—C3—C4	103.02 (8)	C22—C23—H23B	109.1
N1—C4—C25	112.58 (9)	C24—C23—H23B	109.1
N1—C4—C31	110.16 (9)	H23A—C23—H23B	107.9
C25—C4—C31	100.96 (9)	C23—C24—C3	113.42 (10)
N1—C4—C3	103.03 (8)	C23—C24—H24A	108.9
C25—C4—C3	118.06 (9)	C3—C24—H24A	108.9
C31—C4—C3	112.22 (9)	C23—C24—H24B	108.9
N1—C5—H5A	109.5	C3—C24—H24B	108.9
N1—C5—H5B	109.5	H24A—C24—H24B	107.7
H5A—C5—H5B	109.5	C26—C25—C30	119.19 (11)
N1—C5—H5C	109.5	C26—C25—C4	131.81 (11)
H5A—C5—H5C	109.5	C30—C25—C4	109.00 (10)
H5B—C5—H5C	109.5	C25—C26—C27	118.99 (13)
C7—C6—C15	118.79 (12)	C25—C26—H26	120.5
C7—C6—C2	121.02 (12)	C27—C26—H26	120.5
C15—C6—C2	120.13 (11)	C28—C27—C26	120.81 (13)
C6—C7—C8	121.79 (15)	C28—C27—H27	119.6
C6—C7—H7	119.1	C26—C27—H27	119.6
C8—C7—H7	119.1	C27—C28—C29	121.20 (13)
C9—C8—C7	120.01 (16)	C27—C28—H28	119.4
C9—C8—H8	120.0	C29—C28—H28	119.4
C7—C8—H8	120.0	C30—C29—C28	117.41 (13)
C8—C9—C10	121.04 (14)	C30—C29—H29	121.3
C8—C9—H9	119.5	C28—C29—H29	121.3
C10—C9—H9	119.5	C29—C30—C25	122.36 (12)
C9—C10—C11	122.12 (15)	C29—C30—N2	127.39 (12)
C9—C10—C15	119.47 (14)	C25—C30—N2	110.25 (10)
C11—C10—C15	118.41 (17)	O2—C31—N2	125.07 (11)
C12—C11—C10	121.79 (16)	O2—C31—C4	126.21 (11)
C12—C11—H11	119.1	N2—C31—C4	108.64 (10)
C10—C11—H11	119.1	N2—C32—C33	112.50 (12)
C11—C12—C13	119.87 (16)	N2—C32—H32A	109.1
C11—C12—H12	120.1	C33—C32—H32A	109.1
C13—C12—H12	120.1	N2—C32—H32B	109.1
C12—C13—C14	120.98 (19)	C33—C32—H32B	109.1
C12—C13—H13	119.5	H32A—C32—H32B	107.8
C14—C13—H13	119.5	O3—C33—C32	113.01 (12)
C13—C14—C15	121.44 (16)	O3—C33—H33A	109.0
C13—C14—H14	119.3	C32—C33—H33A	109.0
C15—C14—H14	119.3	O3—C33—H33B	109.0
C14—C15—C10	117.47 (13)	C32—C33—H33B	109.0
C14—C15—C6	123.69 (12)	H33A—C33—H33B	107.8
C10—C15—C6	118.82 (13)
C5—N1—C1—C2	−175.59 (10)	O1—C16—C17—C22	179.21 (12)
C4—N1—C1—C2	−47.49 (11)	C3—C16—C17—C22	0.48 (16)
N1—C1—C2—C6	162.32 (10)	O1—C16—C17—C18	0.81 (17)
N1—C1—C2—C3	33.58 (11)	C3—C16—C17—C18	−177.92 (10)
C6—C2—C3—C24	−14.77 (14)	C22—C17—C18—C19	−1.21 (19)
C1—C2—C3—C24	115.21 (10)	C16—C17—C18—C19	177.22 (12)
C6—C2—C3—C16	105.48 (11)	C17—C18—C19—C20	−0.3 (2)
C1—C2—C3—C16	−124.54 (10)	C18—C19—C20—C21	1.6 (2)
C6—C2—C3—C4	−139.17 (10)	C19—C20—C21—C22	−1.3 (2)
C1—C2—C3—C4	−9.19 (11)	C18—C17—C22—C21	1.49 (18)
C5—N1—C4—C25	−63.23 (13)	C16—C17—C22—C21	−176.88 (11)
C1—N1—C4—C25	169.41 (9)	C18—C17—C22—C23	−177.44 (11)
C5—N1—C4—C31	48.61 (13)	C16—C17—C22—C23	4.19 (18)
C1—N1—C4—C31	−78.75 (11)	C20—C21—C22—C17	−0.3 (2)
C5—N1—C4—C3	168.51 (10)	C20—C21—C22—C23	178.64 (13)
C1—N1—C4—C3	41.16 (10)	C17—C22—C23—C24	21.81 (17)
C24—C3—C4—N1	−142.90 (9)	C21—C22—C23—C24	−157.09 (12)
C16—C3—C4—N1	96.87 (10)	C22—C23—C24—C3	−53.54 (14)
C2—C3—C4—N1	−18.23 (10)	C16—C3—C24—C23	55.80 (13)
C24—C3—C4—C25	92.34 (12)	C2—C3—C24—C23	176.56 (10)
C16—C3—C4—C25	−27.88 (13)	C4—C3—C24—C23	−65.12 (13)
C2—C3—C4—C25	−142.98 (9)	N1—C4—C25—C26	−61.43 (16)
C24—C3—C4—C31	−24.43 (13)	C31—C4—C25—C26	−178.86 (12)
C16—C3—C4—C31	−144.66 (9)	C3—C4—C25—C26	58.47 (16)
C2—C3—C4—C31	100.24 (10)	N1—C4—C25—C30	117.98 (10)
C1—C2—C6—C7	−42.55 (17)	C31—C4—C25—C30	0.55 (11)
C3—C2—C6—C7	81.16 (15)	C3—C4—C25—C30	−122.12 (10)
C1—C2—C6—C15	140.16 (12)	C30—C25—C26—C27	2.18 (17)
C3—C2—C6—C15	−96.14 (13)	C4—C25—C26—C27	−178.46 (12)
C15—C6—C7—C8	−0.5 (2)	C25—C26—C27—C28	−0.6 (2)
C2—C6—C7—C8	−177.84 (14)	C26—C27—C28—C29	−1.2 (2)
C6—C7—C8—C9	2.2 (3)	C27—C28—C29—C30	1.3 (2)
C7—C8—C9—C10	−1.3 (3)	C28—C29—C30—C25	0.3 (2)
C8—C9—C10—C11	178.36 (16)	C28—C29—C30—N2	179.84 (13)
C8—C9—C10—C15	−1.2 (2)	C26—C25—C30—C29	−2.08 (18)
C9—C10—C11—C12	178.86 (16)	C4—C25—C30—C29	178.42 (11)
C15—C10—C11—C12	−1.6 (2)	C26—C25—C30—N2	178.34 (10)
C10—C11—C12—C13	−0.3 (3)	C4—C25—C30—N2	−1.16 (13)
C11—C12—C13—C14	1.7 (3)	C31—N2—C30—C29	−178.19 (13)
C12—C13—C14—C15	−1.1 (3)	C32—N2—C30—C29	7.8 (2)
C13—C14—C15—C10	−0.9 (2)	C31—N2—C30—C25	1.36 (14)
C13—C14—C15—C6	177.94 (14)	C32—N2—C30—C25	−172.66 (11)
C9—C10—C15—C14	−178.30 (13)	C30—N2—C31—O2	−177.80 (12)
C11—C10—C15—C14	2.11 (19)	C32—N2—C31—O2	−3.8 (2)
C9—C10—C15—C6	2.82 (19)	C30—N2—C31—C4	−0.96 (13)
C11—C10—C15—C6	−176.76 (12)	C32—N2—C31—C4	173.07 (11)
C7—C6—C15—C14	179.24 (13)	N1—C4—C31—O2	57.84 (15)
C2—C6—C15—C14	−3.40 (18)	C25—C4—C31—O2	177.03 (12)
C7—C6—C15—C10	−1.96 (18)	C3—C4—C31—O2	−56.34 (15)
C2—C6—C15—C10	175.39 (11)	N1—C4—C31—N2	−118.95 (10)
C24—C3—C16—O1	151.83 (12)	C25—C4—C31—N2	0.25 (11)
C2—C3—C16—O1	27.41 (15)	C3—C4—C31—N2	126.88 (10)
C4—C3—C16—O1	−84.06 (13)	C31—N2—C32—C33	−103.09 (15)
C24—C3—C16—C17	−29.45 (13)	C30—N2—C32—C33	70.17 (16)
C2—C3—C16—C17	−153.87 (10)	N2—C32—C33—O3	57.18 (17)
C4—C3—C16—C17	94.66 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1	0.93	2.54	3.198 (2)	128
C24—H24A···O2	0.97	2.42	3.098 (2)	127
C14—H14···O1	0.93	2.59	3.394 (2)	145
C2—H2···O1	0.98	2.21	2.764 (2)	115
C1—H1B···O2	0.97	2.40	3.020 (2)	121
O3—H3···O2i	0.82	2.03	2.830 (1)	164
C20—H20···Cg1ii	0.93	2.71	3.603 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O1	0.93	2.54	3.198 (2)	128
C24—H24A⋯O2	0.97	2.42	3.098 (2)	127
C14—H14⋯O1	0.93	2.59	3.394 (2)	145
C2—H2⋯O1	0.98	2.21	2.764 (2)	115
C1—H1B⋯O2	0.97	2.40	3.020 (2)	121
O3—H3⋯O2i	0.82	2.03	2.830 (1)	164
C20—H20⋯Cg1ii	0.93	2.71	3.603 (2)	161

Symmetry codes: (i) ; (ii) .