2′-(p-Methoxy­benzoyl)-1′,2,2′,3,5′,6′,7′,7a′-octa­hydro-1H-indan-2-spiro-3′-(3′H-pyrrolizine)-1′-spiro-3′′-1H-indoline-1,2′′,3-trione

The pyrrolidine ring of the title compound, C₃₀H₂₄N₂O₅, adopts a half-chair conformation. The structure is stabilized by C—H...O intramolecular interactions and the packing of the mol­ecules is stabilized by C—H...O and N—H...O intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.139
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as multi-scan
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           27.99
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               5528
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5828
           Completeness (_total/calc)             94.85%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C33

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2'-(p-Methoxybenzoyl)-1',2,2',3,5',6',7',7a'-octahydro-1H-indan-2-spiro-3'- (3'H-pyrrolizine)-1'-spiro-3''-1H-indoline-1,2'',3-trione

Crystal data

C30H24N2O5	F(000) = 1032
Mr = 492.51	Dx = 1.352 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3592 reflections
a = 11.4931 (8) Å	θ = 2.3–26°
b = 13.6374 (9) Å	µ = 0.09 mm^−1
c = 15.5377 (10) Å	T = 293 K
β = 96.351 (1)°	Prisms, yellow
V = 2420.4 (3) Å^3	0.23 × 0.20 × 0.17 mm
Z = 4

Data collection

CCD Area Detector diffractometer	5528 independent reflections
Radiation source: fine-focus sealed tube	3764 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan	h = −14→14
Tmin = 0.979, Tmax = 0.984	k = −17→17
14548 measured reflections	l = −20→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0798P)^2 + 0.041P] where P = (Fo^2 + 2Fc^2)/3
5528 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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
N1	0.34651 (13)	0.45085 (11)	−0.02912 (10)	0.0450 (4)
H1	0.3818	0.5029	−0.0438	0.054*
C2	0.39982 (15)	0.37685 (12)	0.01661 (10)	0.0354 (4)
O3	0.50239 (10)	0.37660 (9)	0.04859 (8)	0.0421 (3)
C4	0.31036 (14)	0.29370 (12)	0.02195 (10)	0.0343 (4)
C5	0.19908 (14)	0.34145 (13)	−0.01848 (10)	0.0368 (4)
C6	0.08488 (16)	0.30866 (14)	−0.03079 (12)	0.0468 (5)
H6	0.0652	0.2473	−0.0107	0.056*
C7	−0.00001 (17)	0.36872 (16)	−0.07364 (14)	0.0588 (6)
H7	−0.0774	0.3477	−0.0817	0.071*
C8	0.02888 (19)	0.45914 (17)	−0.10443 (14)	0.0636 (6)
H8	−0.0293	0.4984	−0.1330	0.076*
C9	0.14330 (19)	0.49249 (16)	−0.09349 (13)	0.0584 (5)
H9	0.1631	0.5532	−0.1149	0.070*
C10	0.22643 (16)	0.43324 (13)	−0.05017 (11)	0.0425 (4)
C11	0.31411 (14)	0.25104 (11)	0.11563 (10)	0.0316 (4)
H11	0.3877	0.2742	0.1469	0.038*
C12	0.21902 (14)	0.27534 (12)	0.17327 (11)	0.0359 (4)
O13	0.15552 (13)	0.20928 (10)	0.19249 (10)	0.0604 (4)
C14	0.21215 (13)	0.37325 (11)	0.21284 (10)	0.0332 (4)
C15	0.28086 (15)	0.45256 (13)	0.19315 (12)	0.0421 (4)
H15	0.3320	0.4455	0.1512	0.051*
C16	0.27441 (16)	0.54110 (13)	0.23467 (12)	0.0457 (4)
H16	0.3194	0.5937	0.2196	0.055*
C17	0.20125 (14)	0.55203 (12)	0.29868 (11)	0.0380 (4)
C18	0.13261 (16)	0.47423 (13)	0.31983 (11)	0.0429 (4)
H18	0.0831	0.4811	0.3629	0.051*
C19	0.13832 (15)	0.38662 (13)	0.27653 (11)	0.0411 (4)
H19	0.0912	0.3348	0.2905	0.049*
C20	0.32788 (14)	0.13979 (11)	0.10581 (10)	0.0329 (4)
C21	0.21731 (14)	0.07491 (12)	0.08790 (11)	0.0360 (4)
O22	0.13732 (11)	0.08654 (9)	0.03124 (8)	0.0484 (3)
C23	0.23388 (15)	−0.01185 (12)	0.14532 (11)	0.0376 (4)
C24	0.16536 (17)	−0.09573 (13)	0.14597 (12)	0.0469 (5)
H24	0.0973	−0.1028	0.1081	0.056*
C25	0.2021 (2)	−0.16837 (14)	0.20501 (14)	0.0564 (5)
H25	0.1576	−0.2252	0.2070	0.068*
C26	0.3031 (2)	−0.15828 (15)	0.26099 (14)	0.0583 (6)
H26	0.3263	−0.2090	0.2991	0.070*
C27	0.37036 (18)	−0.07499 (14)	0.26171 (12)	0.0498 (5)
H27	0.4376	−0.0679	0.3004	0.060*
C28	0.33427 (15)	−0.00196 (12)	0.20270 (11)	0.0381 (4)
C29	0.39017 (15)	0.09307 (12)	0.18893 (11)	0.0370 (4)
O30	0.46823 (11)	0.13134 (9)	0.23561 (8)	0.0508 (3)
N31	0.39098 (12)	0.12556 (10)	0.03008 (9)	0.0372 (3)
C32	0.51955 (15)	0.13827 (14)	0.04253 (12)	0.0462 (5)
H32A	0.5585	0.0773	0.0605	0.055*
H32B	0.5421	0.1884	0.0854	0.055*
C33	0.54875 (19)	0.1692 (2)	−0.04613 (15)	0.0671 (6)
H33A	0.5759	0.1134	−0.0770	0.081*
H33B	0.6098	0.2187	−0.0408	0.081*
C34	0.43745 (18)	0.21049 (15)	−0.09419 (12)	0.0519 (5)
H34A	0.4156	0.1740	−0.1471	0.062*
H34B	0.4479	0.2788	−0.1088	0.062*
C35	0.34382 (15)	0.19991 (12)	−0.03212 (11)	0.0386 (4)
H35	0.2723	0.1742	−0.0645	0.046*
O36	0.20315 (12)	0.64125 (9)	0.33735 (9)	0.0537 (4)
C37	0.1288 (2)	0.65794 (18)	0.40243 (16)	0.0761 (7)
H37A	0.1393	0.7238	0.4237	0.114*
H37B	0.1477	0.6126	0.4492	0.114*
H37C	0.0488	0.6487	0.3787	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0444 (9)	0.0412 (8)	0.0488 (9)	−0.0065 (7)	0.0024 (7)	0.0145 (7)
C2	0.0377 (9)	0.0396 (9)	0.0291 (9)	−0.0039 (7)	0.0046 (7)	0.0014 (7)
O3	0.0357 (7)	0.0460 (7)	0.0434 (7)	−0.0077 (5)	−0.0009 (5)	0.0029 (5)
C4	0.0328 (8)	0.0374 (9)	0.0320 (9)	−0.0033 (7)	0.0000 (7)	0.0012 (7)
C5	0.0350 (9)	0.0433 (10)	0.0310 (9)	−0.0006 (7)	−0.0009 (7)	0.0035 (7)
C6	0.0398 (10)	0.0505 (11)	0.0480 (11)	−0.0027 (8)	−0.0045 (8)	0.0040 (8)
C7	0.0387 (11)	0.0724 (15)	0.0617 (14)	0.0015 (10)	−0.0110 (9)	0.0063 (11)
C8	0.0519 (12)	0.0739 (15)	0.0613 (14)	0.0150 (11)	−0.0104 (10)	0.0178 (11)
C9	0.0603 (13)	0.0548 (12)	0.0581 (13)	0.0057 (10)	−0.0020 (10)	0.0231 (10)
C10	0.0427 (10)	0.0480 (10)	0.0363 (10)	−0.0004 (8)	0.0019 (8)	0.0090 (8)
C11	0.0317 (8)	0.0321 (8)	0.0301 (8)	−0.0010 (7)	−0.0008 (6)	0.0020 (6)
C12	0.0354 (9)	0.0375 (9)	0.0344 (9)	−0.0012 (7)	0.0025 (7)	0.0039 (7)
O13	0.0691 (9)	0.0436 (8)	0.0750 (10)	−0.0146 (7)	0.0365 (8)	−0.0077 (7)
C14	0.0299 (8)	0.0361 (9)	0.0328 (9)	0.0031 (7)	0.0001 (7)	0.0030 (7)
C15	0.0386 (9)	0.0427 (10)	0.0475 (11)	−0.0019 (8)	0.0163 (8)	−0.0030 (8)
C16	0.0446 (10)	0.0382 (10)	0.0566 (12)	−0.0074 (8)	0.0163 (9)	−0.0021 (8)
C17	0.0374 (9)	0.0363 (9)	0.0400 (10)	0.0033 (7)	0.0032 (7)	−0.0007 (7)
C18	0.0459 (10)	0.0444 (10)	0.0409 (10)	0.0010 (8)	0.0162 (8)	0.0010 (8)
C19	0.0439 (10)	0.0399 (10)	0.0410 (10)	−0.0033 (8)	0.0113 (8)	0.0050 (7)
C20	0.0340 (8)	0.0326 (8)	0.0314 (9)	−0.0004 (7)	0.0004 (7)	−0.0013 (6)
C21	0.0360 (9)	0.0350 (9)	0.0373 (9)	0.0016 (7)	0.0053 (7)	−0.0048 (7)
O22	0.0438 (7)	0.0473 (7)	0.0508 (8)	−0.0050 (6)	−0.0092 (6)	0.0029 (6)
C23	0.0427 (9)	0.0358 (9)	0.0359 (9)	0.0025 (7)	0.0116 (7)	−0.0013 (7)
C24	0.0497 (11)	0.0401 (10)	0.0527 (12)	−0.0025 (8)	0.0143 (9)	−0.0027 (8)
C25	0.0717 (14)	0.0383 (10)	0.0625 (14)	−0.0058 (10)	0.0217 (11)	0.0047 (9)
C26	0.0769 (15)	0.0450 (11)	0.0550 (13)	0.0085 (10)	0.0155 (11)	0.0150 (9)
C27	0.0611 (12)	0.0469 (11)	0.0414 (11)	0.0073 (9)	0.0056 (9)	0.0085 (8)
C28	0.0448 (10)	0.0374 (9)	0.0328 (9)	0.0052 (7)	0.0076 (7)	−0.0001 (7)
C29	0.0388 (9)	0.0385 (9)	0.0336 (9)	0.0075 (7)	0.0029 (7)	−0.0019 (7)
O30	0.0517 (8)	0.0494 (8)	0.0468 (8)	−0.0001 (6)	−0.0141 (6)	−0.0031 (6)
N31	0.0382 (8)	0.0392 (8)	0.0340 (8)	0.0025 (6)	0.0034 (6)	−0.0030 (6)
C32	0.0373 (10)	0.0506 (11)	0.0509 (12)	0.0064 (8)	0.0062 (8)	−0.0044 (8)
C33	0.0545 (13)	0.0885 (17)	0.0619 (14)	0.0093 (12)	0.0224 (11)	0.0015 (12)
C34	0.0619 (13)	0.0592 (12)	0.0365 (10)	−0.0023 (10)	0.0133 (9)	−0.0058 (9)
C35	0.0425 (10)	0.0408 (10)	0.0315 (9)	−0.0030 (7)	−0.0003 (7)	−0.0020 (7)
O36	0.0604 (9)	0.0410 (7)	0.0630 (9)	−0.0026 (6)	0.0217 (7)	−0.0120 (6)
C37	0.0943 (19)	0.0598 (14)	0.0815 (17)	0.0012 (13)	0.0424 (15)	−0.0217 (12)

Geometric parameters (Å, º)

N1—C2	1.342 (2)	C20—N31	1.462 (2)
N1—C10	1.403 (2)	C20—C29	1.543 (2)
N1—H1	0.8600	C20—C21	1.548 (2)
C2—O3	1.228 (2)	C21—O22	1.211 (2)
C2—C4	1.539 (2)	C21—C23	1.481 (2)
C4—C5	1.509 (2)	C23—C28	1.385 (2)
C4—C11	1.564 (2)	C23—C24	1.389 (2)
C4—C35	1.600 (2)	C24—C25	1.384 (3)
C5—C6	1.380 (2)	C24—H24	0.9300
C5—C10	1.394 (2)	C25—C26	1.379 (3)
C6—H6	0.9300	C25—H25	0.9300
C7—C6	1.386 (3)	C26—C27	1.373 (3)
C7—H7	0.9300	C26—H26	0.9300
C8—C7	1.377 (3)	C27—C28	1.386 (2)
C8—H8	0.9300	C27—H27	0.9300
C9—C8	1.384 (3)	C28—C29	1.473 (2)
C9—H9	0.9300	C29—O30	1.208 (2)
C10—C9	1.370 (3)	N31—C35	1.463 (2)
C11—C12	1.524 (2)	N31—C32	1.479 (2)
C11—C20	1.535 (2)	C32—C33	1.514 (3)
C11—H11	0.9800	C32—H32A	0.9700
C12—O13	1.217 (2)	C32—H32B	0.9700
C12—C14	1.476 (2)	C33—C34	1.516 (3)
C14—C19	1.385 (2)	C33—H33A	0.9700
C14—C15	1.393 (2)	C33—H33B	0.9700
C15—C16	1.375 (2)	C34—C35	1.529 (2)
C15—H15	0.9300	C34—H34A	0.9700
C16—C17	1.380 (2)	C34—H34B	0.9700
C16—H16	0.9300	C35—H35	0.9800
C17—O36	1.356 (2)	O36—C37	1.413 (2)
C17—C18	1.383 (2)	C37—H37A	0.9600
C18—C19	1.376 (2)	C37—H37B	0.9600
C18—H18	0.9300	C37—H37C	0.9600
C19—H19	0.9300
C2—N1—C10	112.0 (1)	C11—C20—C21	119.42 (13)
C2—N1—H1	124.0	C29—C20—C21	102.12 (13)
C10—N1—H1	124.0	O22—C21—C23	125.4 (2)
O3—C2—N1	125.31 (15)	O22—C21—C20	126.7 (2)
O3—C2—C4	126.4 (2)	C23—C21—C20	107.45 (14)
N1—C2—C4	108.3 (1)	C28—C23—C24	120.54 (16)
C5—C4—C2	101.55 (13)	C28—C23—C21	110.64 (15)
C5—C4—C11	118.88 (13)	C24—C23—C21	128.81 (17)
C2—C4—C11	112.00 (13)	C25—C24—C23	117.56 (19)
C5—C4—C35	111.60 (13)	C25—C24—H24	121.2
C2—C4—C35	111.09 (13)	C23—C24—H24	121.2
C11—C4—C35	101.99 (12)	C26—C25—C24	121.36 (19)
C6—C5—C10	119.36 (16)	C26—C25—H25	119.3
C6—C5—C4	131.87 (16)	C24—C25—H25	119.3
C10—C5—C4	108.71 (15)	C27—C26—C25	121.45 (19)
C5—C6—C7	118.89 (18)	C27—C26—H26	119.3
C5—C6—H6	120.6	C25—C26—H26	119.3
C7—C6—H6	120.6	C26—C27—C28	117.53 (19)
C8—C7—C6	120.81 (19)	C26—C27—H27	121.2
C8—C7—H7	119.6	C28—C27—H27	121.2
C6—C7—H7	119.6	C23—C28—C27	121.54 (17)
C7—C8—C9	120.93 (18)	C23—C28—C29	109.76 (14)
C7—C8—H8	119.5	C27—C28—C29	128.70 (17)
C9—C8—H8	119.5	O30—C29—C28	126.9 (2)
C10—C9—C8	117.91 (19)	O30—C29—C20	124.7 (2)
C10—C9—H9	121.0	C28—C29—C20	108.39 (14)
C8—C9—H9	121.0	C20—N31—C35	105.0 (1)
C9—C10—C5	122.08 (18)	C20—N31—C32	117.2 (1)
C9—C10—N1	128.9 (2)	C35—N31—C32	107.27 (13)
C5—C10—N1	109.01 (15)	N31—C32—C33	103.5 (2)
C12—C11—C20	111.22 (13)	N31—C32—H32A	111.1
C12—C11—C4	121.22 (13)	C33—C32—H32A	111.1
C20—C11—C4	105.53 (12)	N31—C32—H32B	111.1
C12—C11—H11	105.9	C33—C32—H32B	111.1
C20—C11—H11	105.9	H32A—C32—H32B	109.0
C4—C11—H11	105.9	C32—C33—C34	106.96 (15)
O13—C12—C14	120.4 (2)	C32—C33—H33A	110.3
O13—C12—C11	118.1 (2)	C34—C33—H33A	110.3
C14—C12—C11	121.09 (14)	C32—C33—H33B	110.3
C19—C14—C15	117.50 (15)	C34—C33—H33B	110.3
C19—C14—C12	118.81 (15)	H33A—C33—H33B	108.6
C15—C14—C12	123.59 (15)	C33—C34—C35	105.58 (16)
C16—C15—C14	121.17 (16)	C33—C34—H34A	110.6
C16—C15—H15	119.4	C35—C34—H34A	110.6
C14—C15—H15	119.4	C33—C34—H34B	110.6
C15—C16—C17	120.13 (16)	C35—C34—H34B	110.6
C15—C16—H16	119.9	H34A—C34—H34B	108.8
C17—C16—H16	119.9	N31—C35—C34	104.3 (1)
O36—C17—C16	115.8 (2)	N31—C35—C4	107.5 (1)
O36—C17—C18	124.4 (2)	C34—C35—C4	118.84 (14)
C16—C17—C18	119.84 (16)	N31—C35—H35	108.6
C19—C18—C17	119.36 (16)	C34—C35—H35	108.6
C19—C18—H18	120.3	C4—C35—H35	108.6
C17—C18—H18	120.3	C17—O36—C37	118.7 (2)
C18—C19—C14	121.98 (16)	O36—C37—H37A	109.5
C18—C19—H19	119.0	O36—C37—H37B	109.5
C14—C19—H19	119.0	H37A—C37—H37B	109.5
N31—C20—C11	106.09 (13)	O36—C37—H37C	109.5
N31—C20—C29	113.2 (1)	H37A—C37—H37C	109.5
C11—C20—C29	111.61 (13)	H37B—C37—H37C	109.5
N31—C20—C21	104.5 (1)
C10—N1—C2—O3	−174.39 (16)	C4—C11—C20—C21	−88.38 (16)
C10—N1—C2—C4	5.41 (19)	N31—C20—C21—O22	−66.2 (2)
O3—C2—C4—C5	173.03 (16)	C11—C20—C21—O22	52.1 (2)
N1—C2—C4—C5	−6.76 (17)	C29—C20—C21—O22	175.68 (16)
O3—C2—C4—C11	45.1 (2)	N31—C20—C21—C23	106.45 (14)
N1—C2—C4—C11	−134.66 (14)	C11—C20—C21—C23	−135.25 (14)
O3—C2—C4—C35	−68.2 (2)	C29—C20—C21—C23	−11.64 (16)
N1—C2—C4—C35	112.02 (15)	O22—C21—C23—C28	179.77 (16)
C2—C4—C5—C6	−177.01 (18)	C20—C21—C23—C28	6.97 (18)
C11—C4—C5—C6	−53.7 (3)	O22—C21—C23—C24	1.0 (3)
C35—C4—C5—C6	64.6 (2)	C20—C21—C23—C24	−171.84 (17)
C2—C4—C5—C10	5.87 (18)	C28—C23—C24—C25	−0.7 (3)
C11—C4—C5—C10	129.18 (16)	C21—C23—C24—C25	178.01 (17)
C35—C4—C5—C10	−112.55 (16)	C23—C24—C25—C26	−0.3 (3)
C6—C5—C10—C9	−0.1 (3)	C24—C25—C26—C27	1.3 (3)
C4—C5—C10—C9	177.49 (18)	C25—C26—C27—C28	−1.3 (3)
C6—C5—C10—N1	179.31 (16)	C24—C23—C28—C27	0.6 (3)
C4—C5—C10—N1	−3.1 (2)	C21—C23—C28—C27	−178.28 (15)
C2—N1—C10—C9	177.8 (2)	C24—C23—C28—C29	−179.77 (15)
C2—N1—C10—C5	−1.5 (2)	C21—C23—C28—C29	1.31 (19)
C5—C10—C9—C8	0.8 (3)	C26—C27—C28—C23	0.4 (3)
N1—C10—C9—C8	−178.4 (2)	C26—C27—C28—C29	−179.13 (18)
C10—C9—C8—C7	−0.8 (3)	C23—C28—C29—O30	168.03 (17)
C9—C8—C7—C6	0.0 (4)	C27—C28—C29—O30	−12.4 (3)
C10—C5—C6—C7	−0.7 (3)	C23—C28—C29—C20	−9.14 (18)
C4—C5—C6—C7	−177.61 (18)	C27—C28—C29—C20	170.42 (17)
C8—C7—C6—C5	0.8 (3)	N31—C20—C29—O30	83.6 (2)
C5—C4—C11—C12	−13.1 (2)	C11—C20—C29—O30	−36.0 (2)
C2—C4—C11—C12	104.92 (16)	C21—C20—C29—O30	−164.72 (16)
C35—C4—C11—C12	−136.24 (15)	N31—C20—C29—C28	−99.18 (15)
C5—C4—C11—C20	114.35 (15)	C11—C20—C29—C28	141.23 (13)
C2—C4—C11—C20	−127.66 (14)	C21—C20—C29—C28	12.52 (16)
C35—C4—C11—C20	−8.81 (15)	C11—C20—N31—C35	−38.52 (15)
C20—C11—C12—O13	−11.1 (2)	C29—C20—N31—C35	−161.22 (13)
C4—C11—C12—O13	113.75 (18)	C21—C20—N31—C35	88.52 (14)
C20—C11—C12—C14	162.14 (14)	C11—C20—N31—C32	80.38 (17)
C4—C11—C12—C14	−73.0 (2)	C29—C20—N31—C32	−42.32 (19)
O13—C12—C14—C19	4.5 (2)	C21—C20—N31—C32	−152.58 (14)
C11—C12—C14—C19	−168.55 (15)	C20—N31—C32—C33	−152.71 (16)
O13—C12—C14—C15	−179.13 (17)	C35—N31—C32—C33	−35.03 (19)
C11—C12—C14—C15	7.8 (2)	N31—C32—C33—C34	21.6 (2)
C19—C14—C15—C16	−0.8 (3)	C32—C33—C34—C35	−1.4 (2)
C12—C14—C15—C16	−177.21 (16)	C20—N31—C35—C34	159.65 (13)
C14—C15—C16—C17	1.7 (3)	C32—N31—C35—C34	34.30 (17)
C15—C16—C17—O36	178.37 (16)	C20—N31—C35—C4	32.63 (16)
C15—C16—C17—C18	−1.3 (3)	C32—N31—C35—C4	−92.72 (15)
O36—C17—C18—C19	−179.61 (16)	C33—C34—C35—N31	−19.6 (2)
C16—C17—C18—C19	0.0 (3)	C33—C34—C35—C4	100.03 (19)
C17—C18—C19—C14	0.9 (3)	C5—C4—C35—N31	−141.98 (14)
C15—C14—C19—C18	−0.5 (3)	C2—C4—C35—N31	105.47 (15)
C12—C14—C19—C18	176.09 (16)	C11—C4—C35—N31	−14.02 (16)
C12—C11—C20—N31	162.32 (13)	C5—C4—C35—C34	100.06 (18)
C4—C11—C20—N31	29.09 (15)	C2—C4—C35—C34	−12.5 (2)
C12—C11—C20—C29	−74.00 (17)	C11—C4—C35—C34	−131.98 (16)
C4—C11—C20—C29	152.76 (13)	C16—C17—O36—C37	178.91 (19)
C12—C11—C20—C21	44.86 (19)	C18—C17—O36—C37	−1.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.86	2.12	2.960 (2)	165
C6—H6···O22	0.93	2.41	3.215 (2)	145
C11—H11···O3	0.98	2.54	3.033 (2)	111
C11—H11···O30	0.98	2.50	2.924 (2)	106
C16—H16···O30	0.93	2.52	3.190 (2)	130
C26—H26···O36	0.93	2.59	3.241 (2)	127
C27—H27···O3	0.93	2.49	3.211 (2)	134
C35—H35···O22	0.98	2.56	3.084 (2)	113

Symmetry code: (i) −x+1, −y+1, −z.