5-Benzoyl-1-cyclo­hexyl-3-(m-nitro­phenyl)-2-phenyl­pyrrolidine-spiro-4,2′-(6′-methoxy-1′-tetralone)

In the title mol­ecule, C₃₉H₃₈N₂O₅, the pyrrolidine ring is in an envelope conformation and the cyclo­hexyl ring adopts a chair conformation. The cyclo­hexanone ring in the tetralone moiety adopts a sofa conformation. The molecular packing in the crystal is stabilized by C—H...π interactions in addition to van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.068
• wR factor = 0.182
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: PARST (Nardelli, 1995) and PLATON (Spek, 1990).

(ar4m)

Crystal data

C39H38N2O5	Z = 2
Mr = 614.71	F(000) = 652
Triclinic, P1	Dx = 1.239 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.2284 (1) Å	Cell parameters from 3239 reflections
b = 12.6346 (4) Å	θ = 2.7–28.4°
c = 12.9056 (3) Å	µ = 0.08 mm^−1
α = 102.453 (2)°	T = 293 K
β = 96.412 (2)°	Slab, yellow
γ = 109.775 (1)°	0.40 × 0.20 × 0.14 mm
V = 1648.05 (7) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	2873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
Detector resolution: 8.33 pixels mm^-1	h = −13→12
ω scans	k = −14→15
9073 measured reflections	l = −15→14
5638 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.182	w = 1/[σ^2(Fo^2) + (0.0773P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max = 0.001
5638 reflections	Δρmax = 0.23 e Å^−3
416 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

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
O1	0.7376 (2)	0.1864 (2)	0.28030 (18)	0.0523 (7)
O2	0.4593 (2)	0.4448 (2)	0.27962 (19)	0.0497 (7)
O3	0.6057 (2)	0.0545 (2)	0.70635 (19)	0.0549 (7)
O4	0.8704 (3)	0.9219 (2)	0.4015 (3)	0.0830 (10)
O5	0.6819 (3)	0.7928 (2)	0.3711 (3)	0.0913 (11)
N1	0.5388 (2)	0.2654 (2)	0.14556 (19)	0.0362 (7)
N2	0.7978 (3)	0.8215 (3)	0.3806 (2)	0.0514 (8)
C1	0.6451 (3)	0.3722 (3)	0.1489 (2)	0.0394 (8)
H1	0.6130	0.4352	0.1483	0.047*
C2	0.7337 (3)	0.3989 (3)	0.2588 (2)	0.0366 (8)
H2	0.7937	0.3590	0.2443	0.044*
C3	0.6468 (3)	0.3339 (3)	0.3302 (2)	0.0329 (8)
C4	0.5091 (3)	0.2726 (3)	0.2545 (2)	0.0343 (8)
H4	0.4683	0.1936	0.2623	0.041*
C5	0.6870 (3)	0.2319 (3)	0.3463 (2)	0.0344 (8)
C6	0.6615 (3)	0.1885 (3)	0.4414 (2)	0.0310 (7)
C7	0.6939 (3)	0.0937 (3)	0.4546 (3)	0.0371 (8)
H7	0.7291	0.0588	0.4017	0.045*
C8	0.6755 (3)	0.0512 (3)	0.5425 (3)	0.0424 (9)
H8	0.6974	−0.0121	0.5489	0.051*
C9	0.6232 (3)	0.1034 (3)	0.6232 (3)	0.0412 (9)
C10	0.5923 (3)	0.1986 (3)	0.6123 (3)	0.0375 (8)
H10	0.5596	0.2346	0.6665	0.045*
C11	0.6092 (3)	0.2410 (3)	0.5222 (2)	0.0326 (8)
C12	0.5740 (3)	0.3429 (3)	0.5106 (3)	0.0398 (8)
H12A	0.5867	0.3945	0.5819	0.048*
H12B	0.4833	0.3148	0.4772	0.048*
C13	0.6542 (3)	0.4112 (3)	0.4426 (2)	0.0379 (8)
H13A	0.7435	0.4477	0.4807	0.045*
H13B	0.6241	0.4728	0.4334	0.045*
C14	0.5360 (4)	0.0945 (4)	0.7822 (3)	0.0643 (12)
H14A	0.5301	0.0534	0.8370	0.096*
H14B	0.4507	0.0801	0.7451	0.096*
H14C	0.5805	0.1767	0.8152	0.096*
C15	0.8174 (3)	0.5271 (3)	0.3077 (3)	0.0380 (8)
C16	0.7673 (3)	0.6145 (3)	0.3225 (2)	0.0372 (8)
H16	0.6788	0.5959	0.3045	0.045*
C17	0.8509 (3)	0.7294 (3)	0.3644 (3)	0.0383 (8)
C18	0.9820 (3)	0.7624 (3)	0.3925 (3)	0.0538 (10)
H18	1.0357	0.8406	0.4207	0.065*
C19	1.0313 (3)	0.6758 (3)	0.3773 (3)	0.0646 (12)
H19	1.1201	0.6954	0.3951	0.077*
C20	0.9501 (3)	0.5593 (3)	0.3357 (3)	0.0566 (10)
H20	0.9854	0.5019	0.3264	0.068*
C21	0.7152 (3)	0.3568 (3)	0.0559 (3)	0.0508 (10)
C22	0.7393 (5)	0.4332 (4)	−0.0071 (4)	0.0860 (15)
H22	0.7070	0.4926	0.0029	0.103*
C23	0.8132 (7)	0.4216 (6)	−0.0872 (5)	0.123 (2)
H23	0.8281	0.4726	−0.1309	0.148*
C24	0.8625 (6)	0.3372 (7)	−0.1009 (5)	0.114 (2)
H24	0.9133	0.3318	−0.1525	0.137*
C25	0.8389 (5)	0.2603 (5)	−0.0405 (4)	0.0894 (16)
H25	0.8714	0.2011	−0.0518	0.107*
C26	0.7659 (4)	0.2697 (4)	0.0386 (3)	0.0638 (12)
H26	0.7507	0.2170	0.0805	0.077*
C27	0.4212 (3)	0.3417 (3)	0.2797 (3)	0.0377 (8)
C28	0.2875 (3)	0.2811 (3)	0.2944 (3)	0.0408 (8)
C29	0.2465 (3)	0.1741 (3)	0.3161 (3)	0.0523 (10)
H29	0.3046	0.1371	0.3232	0.063*
C30	0.1209 (4)	0.1200 (4)	0.3277 (3)	0.0645 (12)
H30	0.0951	0.0477	0.3426	0.077*
C31	0.0357 (4)	0.1740 (4)	0.3169 (4)	0.0806 (14)
H31	−0.0486	0.1386	0.3252	0.097*
C32	0.0728 (4)	0.2794 (5)	0.2939 (5)	0.1016 (19)
H32	0.0130	0.3142	0.2841	0.122*
C33	0.1993 (4)	0.3346 (4)	0.2854 (4)	0.0778 (14)
H33	0.2253	0.4083	0.2734	0.093*
C34	0.4344 (3)	0.2157 (3)	0.0484 (3)	0.0450 (9)
H34	0.4770	0.2026	−0.0128	0.054*
C35	0.3634 (4)	0.2942 (3)	0.0235 (3)	0.0664 (12)
H35A	0.3179	0.3099	0.0811	0.080*
H35B	0.4255	0.3681	0.0206	0.080*
C36	0.2671 (5)	0.2359 (4)	−0.0844 (4)	0.0886 (16)
H36A	0.2212	0.2860	−0.0973	0.106*
H36B	0.3135	0.2261	−0.1425	0.106*
C37	0.1725 (5)	0.1201 (4)	−0.0851 (4)	0.0870 (15)
H37A	0.1146	0.0843	−0.1553	0.104*
H37B	0.1212	0.1303	−0.0308	0.104*
C38	0.2409 (4)	0.0407 (4)	−0.0618 (3)	0.0713 (13)
H38A	0.2843	0.0235	−0.1205	0.086*
H38B	0.1778	−0.0324	−0.0583	0.086*
C39	0.3401 (4)	0.0969 (3)	0.0451 (3)	0.0592 (11)
H39A	0.2952	0.1040	0.1047	0.071*
H39B	0.3870	0.0466	0.0544	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0681 (17)	0.0586 (16)	0.0495 (15)	0.0436 (14)	0.0263 (13)	0.0137 (12)
O2	0.0451 (15)	0.0411 (15)	0.0661 (17)	0.0221 (12)	0.0117 (12)	0.0109 (13)
O3	0.0654 (18)	0.0645 (17)	0.0468 (15)	0.0322 (14)	0.0149 (13)	0.0244 (13)
O4	0.062 (2)	0.0354 (16)	0.146 (3)	0.0154 (15)	0.0224 (18)	0.0186 (17)
O5	0.0426 (19)	0.0581 (18)	0.166 (3)	0.0250 (15)	0.0149 (18)	0.0082 (19)
N1	0.0339 (16)	0.0380 (16)	0.0323 (15)	0.0118 (13)	0.0029 (12)	0.0053 (12)
N2	0.042 (2)	0.042 (2)	0.070 (2)	0.0163 (16)	0.0116 (16)	0.0128 (16)
C1	0.044 (2)	0.0362 (19)	0.0392 (19)	0.0171 (16)	0.0069 (16)	0.0096 (15)
C2	0.0323 (19)	0.0346 (18)	0.0438 (19)	0.0141 (15)	0.0104 (15)	0.0080 (15)
C3	0.0325 (18)	0.0322 (17)	0.0358 (18)	0.0174 (14)	0.0058 (14)	0.0049 (14)
C4	0.0312 (18)	0.0328 (18)	0.0380 (18)	0.0142 (14)	0.0058 (14)	0.0047 (15)
C5	0.0269 (17)	0.0365 (18)	0.0380 (19)	0.0151 (15)	0.0015 (14)	0.0033 (15)
C6	0.0247 (17)	0.0283 (17)	0.0360 (18)	0.0104 (14)	−0.0025 (13)	0.0043 (14)
C7	0.0303 (19)	0.0398 (19)	0.040 (2)	0.0141 (15)	0.0062 (14)	0.0079 (16)
C8	0.039 (2)	0.041 (2)	0.051 (2)	0.0207 (17)	0.0046 (16)	0.0130 (18)
C9	0.035 (2)	0.046 (2)	0.040 (2)	0.0101 (17)	−0.0002 (15)	0.0174 (17)
C10	0.0302 (19)	0.044 (2)	0.0364 (19)	0.0133 (16)	0.0029 (14)	0.0086 (16)
C11	0.0232 (17)	0.0332 (18)	0.0372 (19)	0.0104 (14)	−0.0018 (14)	0.0050 (15)
C12	0.039 (2)	0.044 (2)	0.0360 (18)	0.0206 (16)	0.0065 (15)	0.0014 (16)
C13	0.040 (2)	0.0311 (18)	0.0407 (19)	0.0166 (15)	0.0038 (15)	0.0025 (15)
C14	0.078 (3)	0.074 (3)	0.050 (2)	0.034 (2)	0.021 (2)	0.023 (2)
C15	0.0323 (19)	0.0361 (19)	0.0422 (19)	0.0109 (15)	0.0044 (15)	0.0083 (16)
C16	0.0251 (17)	0.0380 (19)	0.046 (2)	0.0104 (15)	0.0053 (14)	0.0094 (16)
C17	0.0319 (19)	0.0363 (19)	0.047 (2)	0.0147 (16)	0.0090 (15)	0.0082 (16)
C18	0.035 (2)	0.043 (2)	0.071 (3)	0.0083 (18)	−0.0005 (18)	0.0057 (19)
C19	0.025 (2)	0.053 (2)	0.101 (3)	0.0101 (19)	0.001 (2)	0.003 (2)
C20	0.031 (2)	0.052 (2)	0.083 (3)	0.0214 (18)	0.0032 (19)	0.006 (2)
C21	0.051 (2)	0.046 (2)	0.043 (2)	0.0047 (19)	0.0046 (17)	0.0099 (18)
C22	0.118 (4)	0.064 (3)	0.077 (3)	0.025 (3)	0.029 (3)	0.030 (3)
C23	0.166 (7)	0.111 (5)	0.096 (4)	0.025 (5)	0.073 (4)	0.055 (4)
C24	0.117 (5)	0.133 (6)	0.082 (4)	0.026 (4)	0.057 (4)	0.027 (4)
C25	0.086 (4)	0.118 (4)	0.070 (3)	0.046 (3)	0.037 (3)	0.013 (3)
C26	0.069 (3)	0.075 (3)	0.052 (2)	0.032 (2)	0.026 (2)	0.011 (2)
C27	0.037 (2)	0.036 (2)	0.0380 (19)	0.0154 (16)	0.0003 (15)	0.0060 (16)
C28	0.0320 (19)	0.044 (2)	0.047 (2)	0.0181 (16)	0.0072 (15)	0.0058 (17)
C29	0.038 (2)	0.067 (3)	0.061 (2)	0.0239 (19)	0.0130 (18)	0.028 (2)
C30	0.046 (3)	0.073 (3)	0.078 (3)	0.018 (2)	0.020 (2)	0.029 (2)
C31	0.047 (3)	0.080 (3)	0.114 (4)	0.025 (2)	0.033 (3)	0.013 (3)
C32	0.043 (3)	0.077 (3)	0.195 (6)	0.037 (3)	0.031 (3)	0.030 (4)
C33	0.046 (3)	0.052 (3)	0.136 (4)	0.026 (2)	0.018 (3)	0.016 (3)
C34	0.048 (2)	0.046 (2)	0.038 (2)	0.0210 (18)	−0.0014 (16)	0.0068 (16)
C35	0.072 (3)	0.059 (3)	0.059 (3)	0.029 (2)	−0.020 (2)	0.007 (2)
C36	0.099 (4)	0.078 (3)	0.072 (3)	0.041 (3)	−0.036 (3)	0.001 (3)
C37	0.071 (3)	0.087 (4)	0.076 (3)	0.025 (3)	−0.029 (2)	−0.003 (3)
C38	0.062 (3)	0.057 (3)	0.067 (3)	0.011 (2)	−0.014 (2)	−0.004 (2)
C39	0.053 (2)	0.044 (2)	0.065 (3)	0.0106 (19)	−0.0076 (19)	0.0036 (19)

Geometric parameters (Å, º)

O1—C5	1.224 (3)	C18—C19	1.372 (5)
O2—C27	1.226 (4)	C18—H18	0.93
O3—C9	1.351 (4)	C19—C20	1.389 (5)
O3—C14	1.432 (4)	C19—H19	0.93
O4—N2	1.204 (3)	C20—H20	0.93
O5—N2	1.212 (4)	C21—C22	1.371 (5)
N1—C1	1.456 (4)	C21—C26	1.389 (5)
N1—C4	1.472 (4)	C22—C23	1.409 (7)
N1—C34	1.475 (4)	C22—H22	0.93
N2—C17	1.464 (4)	C23—C24	1.348 (8)
C1—C21	1.521 (5)	C23—H23	0.93
C1—C2	1.538 (5)	C24—C25	1.349 (7)
C1—H1	0.98	C24—H24	0.93
C2—C15	1.516 (4)	C25—C26	1.389 (5)
C2—C3	1.570 (4)	C25—H25	0.93
C2—H2	0.98	C26—H26	0.93
C3—C13	1.540 (4)	C27—C28	1.492 (4)
C3—C5	1.547 (4)	C28—C29	1.374 (5)
C3—C4	1.571 (4)	C28—C33	1.382 (5)
C4—C27	1.542 (4)	C29—C30	1.384 (5)
C4—H4	0.98	C29—H29	0.93
C5—C6	1.467 (4)	C30—C31	1.361 (6)
C6—C7	1.401 (4)	C30—H30	0.93
C6—C11	1.405 (4)	C31—C32	1.363 (6)
C7—C8	1.363 (4)	C31—H31	0.93
C7—H7	0.93	C32—C33	1.385 (6)
C8—C9	1.402 (5)	C32—H32	0.93
C8—H8	0.93	C33—H33	0.93
C9—C10	1.389 (5)	C34—C39	1.505 (5)
C10—C11	1.387 (4)	C34—C35	1.528 (5)
C10—H10	0.93	C34—H34	0.98
C11—C12	1.500 (4)	C35—C36	1.528 (5)
C12—C13	1.517 (4)	C35—H35A	0.97
C12—H12A	0.97	C35—H35B	0.97
C12—H12B	0.97	C36—C37	1.486 (6)
C13—H13A	0.97	C36—H36A	0.97
C13—H13B	0.97	C36—H36B	0.97
C14—H14A	0.96	C37—C38	1.511 (6)
C14—H14B	0.96	C37—H37A	0.97
C14—H14C	0.96	C37—H37B	0.97
C15—C20	1.386 (4)	C38—C39	1.532 (5)
C15—C16	1.388 (4)	C38—H38A	0.97
C16—C17	1.382 (4)	C38—H38B	0.97
C16—H16	0.93	C39—H39A	0.97
C17—C18	1.368 (4)	C39—H39B	0.97
C9—O3—C14	117.4 (3)	C18—C19—C20	120.7 (3)
C1—N1—C4	108.9 (2)	C18—C19—H19	119.6
C1—N1—C34	116.8 (3)	C20—C19—H19	119.6
C4—N1—C34	120.8 (2)	C15—C20—C19	121.1 (3)
O4—N2—O5	122.8 (3)	C15—C20—H20	119.4
O4—N2—C17	119.0 (3)	C19—C20—H20	119.4
O5—N2—C17	118.2 (3)	C22—C21—C26	118.2 (4)
N1—C1—C21	112.6 (3)	C22—C21—C1	121.4 (4)
N1—C1—C2	103.0 (2)	C26—C21—C1	120.2 (3)
C21—C1—C2	111.4 (3)	C21—C22—C23	119.9 (5)
N1—C1—H1	109.9	C21—C22—H22	120.0
C21—C1—H1	109.9	C23—C22—H22	120.0
C2—C1—H1	109.9	C24—C23—C22	120.4 (6)
C15—C2—C1	114.4 (3)	C24—C23—H23	119.8
C15—C2—C3	117.8 (2)	C22—C23—H23	119.8
C1—C2—C3	106.4 (2)	C23—C24—C25	120.6 (5)
C15—C2—H2	105.8	C23—C24—H24	119.7
C1—C2—H2	105.8	C25—C24—H24	119.7
C3—C2—H2	105.8	C24—C25—C26	120.0 (5)
C13—C3—C5	108.4 (2)	C24—C25—H25	120.0
C13—C3—C2	114.7 (2)	C26—C25—H25	120.0
C5—C3—C2	108.7 (2)	C25—C26—C21	120.9 (5)
C13—C3—C4	116.0 (2)	C25—C26—H26	119.6
C5—C3—C4	104.5 (2)	C21—C26—H26	119.6
C2—C3—C4	103.9 (2)	O2—C27—C28	120.6 (3)
N1—C4—C27	113.2 (3)	O2—C27—C4	119.0 (3)
N1—C4—C3	102.7 (2)	C28—C27—C4	120.2 (3)
C27—C4—C3	112.2 (2)	C29—C28—C33	117.9 (3)
N1—C4—H4	109.5	C29—C28—C27	123.5 (3)
C27—C4—H4	109.5	C33—C28—C27	118.6 (3)
C3—C4—H4	109.5	C28—C29—C30	121.7 (4)
O1—C5—C6	120.0 (3)	C28—C29—H29	119.1
O1—C5—C3	121.0 (3)	C30—C29—H29	119.1
C6—C5—C3	119.0 (3)	C31—C30—C29	119.1 (4)
C7—C6—C11	118.4 (3)	C31—C30—H30	120.4
C7—C6—C5	119.3 (3)	C29—C30—H30	120.4
C11—C6—C5	122.3 (3)	C30—C31—C32	120.6 (4)
C8—C7—C6	122.0 (3)	C30—C31—H31	119.7
C8—C7—H7	119.0	C32—C31—H31	119.7
C6—C7—H7	119.0	C31—C32—C33	120.0 (4)
C7—C8—C9	119.7 (3)	C31—C32—H32	120.0
C7—C8—H8	120.2	C33—C32—H32	120.0
C9—C8—H8	120.2	C28—C33—C32	120.6 (4)
O3—C9—C10	125.0 (3)	C28—C33—H33	119.7
O3—C9—C8	115.8 (3)	C32—C33—H33	119.7
C10—C9—C8	119.1 (3)	N1—C34—C39	112.5 (3)
C11—C10—C9	121.4 (3)	N1—C34—C35	116.6 (3)
C11—C10—H10	119.3	C39—C34—C35	110.8 (3)
C9—C10—H10	119.3	N1—C34—H34	105.3
C10—C11—C6	119.4 (3)	C39—C34—H34	105.3
C10—C11—C12	121.0 (3)	C35—C34—H34	105.3
C6—C11—C12	119.7 (3)	C36—C35—C34	110.8 (3)
C11—C12—C13	112.1 (3)	C36—C35—H35A	109.5
C11—C12—H12A	109.2	C34—C35—H35A	109.5
C13—C12—H12A	109.2	C36—C35—H35B	109.5
C11—C12—H12B	109.2	C34—C35—H35B	109.5
C13—C12—H12B	109.2	H35A—C35—H35B	108.1
H12A—C12—H12B	107.9	C37—C36—C35	111.5 (4)
C12—C13—C3	112.6 (2)	C37—C36—H36A	109.3
C12—C13—H13A	109.1	C35—C36—H36A	109.3
C3—C13—H13A	109.1	C37—C36—H36B	109.3
C12—C13—H13B	109.1	C35—C36—H36B	109.3
C3—C13—H13B	109.1	H36A—C36—H36B	108.0
H13A—C13—H13B	107.8	C36—C37—C38	110.8 (4)
O3—C14—H14A	109.5	C36—C37—H37A	109.5
O3—C14—H14B	109.5	C38—C37—H37A	109.5
H14A—C14—H14B	109.5	C36—C37—H37B	109.5
O3—C14—H14C	109.5	C38—C37—H37B	109.5
H14A—C14—H14C	109.5	H37A—C37—H37B	108.1
H14B—C14—H14C	109.5	C37—C38—C39	111.4 (3)
C20—C15—C16	118.2 (3)	C37—C38—H38A	109.3
C20—C15—C2	118.9 (3)	C39—C38—H38A	109.3
C16—C15—C2	122.8 (3)	C37—C38—H38B	109.3
C17—C16—C15	119.0 (3)	C39—C38—H38B	109.3
C17—C16—H16	120.5	H38A—C38—H38B	108.0
C15—C16—H16	120.5	C34—C39—C38	112.0 (3)
C18—C17—C16	123.3 (3)	C34—C39—H39A	109.2
C18—C17—N2	117.7 (3)	C38—C39—H39A	109.2
C16—C17—N2	119.0 (3)	C34—C39—H39B	109.2
C17—C18—C19	117.5 (3)	C38—C39—H39B	109.2
C17—C18—H18	121.2	H39A—C39—H39B	107.9
C19—C18—H18	121.2
C4—N1—C1—C21	158.7 (3)	C1—C2—C15—C16	53.0 (4)
C34—N1—C1—C21	−60.1 (4)	C3—C2—C15—C16	−73.2 (4)
C4—N1—C1—C2	38.6 (3)	C20—C15—C16—C17	0.0 (5)
C34—N1—C1—C2	179.8 (3)	C2—C15—C16—C17	−177.9 (3)
N1—C1—C2—C15	−153.8 (2)	C15—C16—C17—C18	0.0 (5)
C21—C1—C2—C15	85.2 (3)	C15—C16—C17—N2	−179.6 (3)
N1—C1—C2—C3	−22.0 (3)	O4—N2—C17—C18	11.3 (5)
C21—C1—C2—C3	−142.9 (3)	O5—N2—C17—C18	−169.5 (3)
C15—C2—C3—C13	1.9 (4)	O4—N2—C17—C16	−169.0 (3)
C1—C2—C3—C13	−128.0 (3)	O5—N2—C17—C16	10.2 (5)
C15—C2—C3—C5	−119.5 (3)	C16—C17—C18—C19	0.3 (5)
C1—C2—C3—C5	110.5 (3)	N2—C17—C18—C19	179.9 (3)
C15—C2—C3—C4	129.6 (3)	C17—C18—C19—C20	−0.4 (6)
C1—C2—C3—C4	−0.4 (3)	C16—C15—C20—C19	−0.1 (5)
C1—N1—C4—C27	82.5 (3)	C2—C15—C20—C19	177.8 (4)
C34—N1—C4—C27	−56.9 (4)	C18—C19—C20—C15	0.4 (6)
C1—N1—C4—C3	−38.8 (3)	N1—C1—C21—C22	130.1 (4)
C34—N1—C4—C3	−178.1 (3)	C2—C1—C21—C22	−114.8 (4)
C13—C3—C4—N1	149.1 (3)	N1—C1—C21—C26	−55.3 (4)
C5—C3—C4—N1	−91.6 (3)	C2—C1—C21—C26	59.9 (4)
C2—C3—C4—N1	22.3 (3)	C26—C21—C22—C23	0.3 (7)
C13—C3—C4—C27	27.3 (4)	C1—C21—C22—C23	175.1 (4)
C5—C3—C4—C27	146.5 (3)	C21—C22—C23—C24	−1.3 (9)
C2—C3—C4—C27	−99.6 (3)	C22—C23—C24—C25	1.9 (10)
C13—C3—C5—O1	−151.0 (3)	C23—C24—C25—C26	−1.7 (9)
C2—C3—C5—O1	−25.8 (4)	C24—C25—C26—C21	0.7 (7)
C4—C3—C5—O1	84.7 (3)	C22—C21—C26—C25	0.0 (6)
C13—C3—C5—C6	30.1 (4)	C1—C21—C26—C25	−174.9 (4)
C2—C3—C5—C6	155.3 (3)	N1—C4—C27—O2	−61.3 (4)
C4—C3—C5—C6	−94.3 (3)	C3—C4—C27—O2	54.4 (4)
O1—C5—C6—C7	−1.0 (4)	N1—C4—C27—C28	113.5 (3)
C3—C5—C6—C7	178.0 (3)	C3—C4—C27—C28	−130.8 (3)
O1—C5—C6—C11	176.9 (3)	O2—C27—C28—C29	−167.0 (3)
C3—C5—C6—C11	−4.1 (4)	C4—C27—C28—C29	18.3 (5)
C11—C6—C7—C8	0.4 (4)	O2—C27—C28—C33	13.3 (5)
C5—C6—C7—C8	178.4 (3)	C4—C27—C28—C33	−161.4 (3)
C6—C7—C8—C9	−0.4 (5)	C33—C28—C29—C30	0.6 (5)
C14—O3—C9—C10	7.9 (5)	C27—C28—C29—C30	−179.1 (3)
C14—O3—C9—C8	−171.4 (3)	C28—C29—C30—C31	0.3 (6)
C7—C8—C9—O3	178.7 (3)	C29—C30—C31—C32	0.6 (7)
C7—C8—C9—C10	−0.6 (5)	C30—C31—C32—C33	−2.4 (8)
O3—C9—C10—C11	−177.7 (3)	C29—C28—C33—C32	−2.4 (6)
C8—C9—C10—C11	1.5 (5)	C27—C28—C33—C32	177.3 (4)
C9—C10—C11—C6	−1.5 (4)	C31—C32—C33—C28	3.3 (8)
C9—C10—C11—C12	179.3 (3)	C1—N1—C34—C39	171.4 (3)
C7—C6—C11—C10	0.5 (4)	C4—N1—C34—C39	−52.3 (4)
C5—C6—C11—C10	−177.4 (3)	C1—N1—C34—C35	−58.9 (4)
C7—C6—C11—C12	179.8 (3)	C4—N1—C34—C35	77.4 (4)
C5—C6—C11—C12	1.8 (4)	N1—C34—C35—C36	174.7 (3)
C10—C11—C12—C13	152.3 (3)	C39—C34—C35—C36	−54.8 (5)
C6—C11—C12—C13	−26.9 (4)	C34—C35—C36—C37	57.1 (6)
C11—C12—C13—C3	55.0 (4)	C35—C36—C37—C38	−57.3 (5)
C5—C3—C13—C12	−55.3 (3)	C36—C37—C38—C39	55.5 (5)
C2—C3—C13—C12	−177.0 (3)	N1—C34—C39—C38	−173.7 (3)
C4—C3—C13—C12	61.8 (4)	C35—C34—C39—C38	53.7 (4)
C1—C2—C15—C20	−124.9 (3)	C37—C38—C39—C34	−54.2 (5)
C3—C2—C15—C20	109.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2	0.97	2.43	3.063 (4)	122
C16—H16···O2	0.93	2.49	3.303 (4)	146
C14—H14C···Cg(A)^i	0.96	2.83	3.653 (5)	144
C19—H19···Cg(B)^ii	0.93	2.65	3.488 (4)	151

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