1′-(4-Methoxy­benzoyl)­acenaphthene-1-spiro-3′-pyrrolizidine-2′-spiro-3′′-1H-indole-2,2′′(1H,3′′H)-dione

The N—C and C—C bond distances in the pyrrolizidine moiety of the title compound, C₃₃H₂₆N₂O₄, are slightly longer than the normal values. This is due to the steric forces caused by bulky substituents on the pyrrolizidine ring system. The acenaphthene ketone O atom is −0.214 (3) Å from the acenaphthene plane, while the indole ketone O atom is displaced by only 0.004 (3) Å from the indole plane. The molecular structure is stabilized by intramolecular C—H...O interactions. The crystal packing is stabilized by C—H...O intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.085
• wR factor = 0.196
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.59 Ratio

Alert level C
WEIGH01_ALERT_1_C  Extra text has been found in the
            _refine_ls_weighting_scheme field. This should be in the
            _refine_ls_weighting_details field.
            Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.2551
            Weighting scheme identified as calc
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.67
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       5.64 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C33
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT420_ALERT_2_C D-H Without Acceptor       N7     -   H7     ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C33 H26 N2 O4

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 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: 'ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1'-(4-Methoxybenzoyl)acenaphthene-1-spiro-3'-pyrrolizidine-2'-spiro-3''- 1H-indole-2,2''(1H,3''H)-dione

Crystal data

C33H26N2O4	Z = 2
Mr = 514.56	F(000) = 540
Triclinic, P1	Dx = 1.326 Mg m^−3
a = 10.2215 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6228 (12) Å	Cell parameters from 1062 reflections
c = 12.3584 (13) Å	θ = 2.7–21.0°
α = 104.178 (2)°	µ = 0.09 mm^−1
β = 97.238 (2)°	T = 293 K
γ = 91.499 (2)°	Block, colorless
V = 1288.4 (2) Å^3	0.21 × 0.20 × 0.20 mm

Data collection

CCD Area Detector diffractometer	3011 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.0°, θmin = 1.7°
ω scans	h = −12→11
7866 measured reflections	k = −13→13
5149 independent reflections	l = −16→12

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.09	Calculated w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.2551P] where P = (Fo^2 + 2Fc^2)/3
5149 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.17 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	0.4041 (2)	0.7406 (3)	−0.1519 (2)	0.0392 (7)
C2	0.2854 (3)	0.7508 (3)	−0.0965 (3)	0.0340 (8)
C3	0.1858 (3)	0.7971 (3)	−0.1841 (2)	0.0315 (7)
C4	0.2159 (3)	0.7032 (3)	−0.2958 (3)	0.0387 (8)
H4	0.1758	0.6165	−0.3019	0.046*
C5	0.3663 (3)	0.6984 (3)	−0.2761 (3)	0.0438 (9)
H5	0.4062	0.7609	−0.3107	0.053*
C6	0.0436 (3)	0.7895 (3)	−0.1557 (3)	0.0373 (8)
N7	0.0020 (3)	0.9115 (3)	−0.1332 (2)	0.0463 (8)
H7	−0.0740	0.9311	−0.1130	0.056*
C8	0.0965 (3)	1.0030 (3)	−0.1464 (3)	0.0402 (8)
C9	0.0893 (4)	1.1353 (4)	−0.1291 (3)	0.0580 (11)
H9	0.0146	1.1764	−0.1061	0.070*
C10	0.1966 (5)	1.2050 (4)	−0.1470 (3)	0.0638 (12)
H10	0.1940	1.2945	−0.1366	0.077*
C11	0.3068 (4)	1.1446 (4)	−0.1797 (3)	0.0577 (11)
H11	0.3784	1.1938	−0.1905	0.069*
C12	0.3131 (4)	1.0113 (3)	−0.1971 (3)	0.0471 (9)
H12	0.3878	0.9706	−0.2204	0.057*
C13	0.2070 (3)	0.9399 (3)	−0.1791 (3)	0.0335 (7)
C14	0.1615 (4)	0.7491 (4)	−0.3995 (3)	0.0450 (9)
C15	0.0162 (4)	0.7375 (4)	−0.4342 (3)	0.0479 (9)
C16	−0.0657 (4)	0.6459 (4)	−0.4074 (3)	0.0609 (11)
H16	−0.0281	0.5863	−0.3706	0.073*
C17	−0.1995 (4)	0.6416 (5)	−0.4338 (4)	0.0706 (12)
H17	−0.2521	0.5781	−0.4171	0.085*
C18	−0.2556 (4)	0.7303 (5)	−0.4845 (4)	0.0659 (12)
C19	−0.1803 (5)	0.8189 (5)	−0.5185 (3)	0.0712 (13)
H19	−0.2197	0.8758	−0.5575	0.085*
C20	−0.0404 (4)	0.8213 (4)	−0.4926 (3)	0.0651 (12)
H20	0.0128	0.8797	−0.5153	0.078*
C21	0.2999 (3)	0.8380 (3)	0.0227 (3)	0.0349 (8)
C22	0.3448 (3)	0.9648 (3)	0.0680 (3)	0.0438 (9)
H22	0.3789	1.0130	0.0234	0.053*
C23	0.3388 (3)	1.0218 (4)	0.1830 (3)	0.0550 (11)
H23	0.3678	1.1086	0.2129	0.066*
C24	0.2915 (4)	0.9534 (4)	0.2520 (3)	0.0579 (11)
H24	0.2897	0.9940	0.3275	0.069*
C25	0.2457 (3)	0.8218 (4)	0.2094 (3)	0.0488 (9)
C26	0.1907 (4)	0.7378 (5)	0.2670 (3)	0.0618 (12)
H26	0.1848	0.7678	0.3434	0.074*
C27	0.1461 (4)	0.6130 (5)	0.2121 (4)	0.0677 (12)
H27	0.1086	0.5609	0.2520	0.081*
C28	0.1551 (4)	0.5612 (4)	0.0973 (3)	0.0557 (10)
H28	0.1262	0.4756	0.0616	0.067*
C29	0.2076 (3)	0.6402 (3)	0.0399 (3)	0.0413 (8)
C30	0.2523 (3)	0.7687 (3)	0.0949 (3)	0.0380 (8)
C31	0.2310 (3)	0.6172 (3)	−0.0779 (3)	0.0415 (8)
C32	0.5080 (4)	0.6581 (4)	−0.1174 (3)	0.0591 (11)
H32A	0.4741	0.6024	−0.0744	0.071*
H32B	0.5833	0.7113	−0.0718	0.071*
C33	0.5467 (5)	0.5778 (5)	−0.2265 (4)	0.0911 (17)
H33A	0.5706	0.4923	−0.2190	0.109*
H33B	0.6212	0.6203	−0.2476	0.109*
C34	0.4257 (4)	0.5671 (4)	−0.3140 (3)	0.0650 (12)
H34A	0.3646	0.4961	−0.3130	0.078*
H34B	0.4501	0.5546	−0.3891	0.078*
O35	−0.0179 (2)	0.6926 (2)	−0.1497 (2)	0.0548 (7)
O36	0.2189 (3)	0.5149 (2)	−0.1491 (2)	0.0658 (8)
O37	0.2346 (3)	0.7980 (3)	−0.4494 (2)	0.0735 (9)
O38	−0.3931 (3)	0.7256 (3)	−0.4995 (3)	0.0940 (11)
C39	−0.4594 (5)	0.8074 (6)	−0.5559 (5)	0.113 (2)
H39A	−0.5529	0.7924	−0.5583	0.170*
H39B	−0.4379	0.7904	−0.6313	0.170*
H39C	−0.4337	0.8962	−0.5172	0.170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0360 (15)	0.0451 (16)	0.0352 (15)	0.0109 (12)	0.0035 (12)	0.0075 (12)
C2	0.0378 (18)	0.0281 (16)	0.0371 (18)	0.0045 (13)	0.0053 (15)	0.0100 (14)
C3	0.0327 (17)	0.0311 (17)	0.0322 (17)	0.0037 (13)	0.0070 (14)	0.0092 (13)
C4	0.0387 (19)	0.0405 (19)	0.0357 (19)	0.0042 (15)	0.0076 (15)	0.0056 (15)
C5	0.044 (2)	0.050 (2)	0.038 (2)	0.0115 (16)	0.0078 (16)	0.0093 (16)
C6	0.0391 (19)	0.040 (2)	0.0314 (18)	−0.0037 (16)	0.0054 (15)	0.0078 (15)
N7	0.0342 (16)	0.0470 (18)	0.0580 (19)	0.0088 (13)	0.0153 (14)	0.0084 (14)
C8	0.0375 (19)	0.0387 (19)	0.046 (2)	0.0041 (15)	0.0058 (16)	0.0129 (16)
C9	0.062 (3)	0.044 (2)	0.070 (3)	0.024 (2)	0.010 (2)	0.0142 (19)
C10	0.087 (3)	0.034 (2)	0.074 (3)	0.003 (2)	0.006 (2)	0.024 (2)
C11	0.067 (3)	0.045 (2)	0.065 (3)	−0.012 (2)	0.010 (2)	0.024 (2)
C12	0.048 (2)	0.050 (2)	0.050 (2)	0.0044 (18)	0.0134 (17)	0.0224 (18)
C13	0.0367 (18)	0.0366 (18)	0.0305 (17)	0.0046 (14)	0.0055 (14)	0.0141 (14)
C14	0.047 (2)	0.060 (2)	0.0294 (19)	0.0106 (18)	0.0098 (17)	0.0099 (17)
C15	0.050 (2)	0.057 (2)	0.033 (2)	0.0065 (19)	0.0038 (16)	0.0046 (17)
C16	0.052 (2)	0.074 (3)	0.051 (2)	−0.005 (2)	−0.0069 (19)	0.012 (2)
C17	0.060 (3)	0.078 (3)	0.070 (3)	−0.005 (2)	0.000 (2)	0.017 (2)
C18	0.050 (3)	0.078 (3)	0.060 (3)	0.005 (2)	0.006 (2)	−0.002 (2)
C19	0.072 (3)	0.085 (3)	0.054 (3)	0.029 (3)	−0.006 (2)	0.016 (2)
C20	0.061 (3)	0.081 (3)	0.060 (3)	0.021 (2)	0.012 (2)	0.028 (2)
C21	0.0327 (17)	0.0355 (18)	0.0360 (18)	0.0034 (14)	0.0033 (14)	0.0085 (15)
C22	0.0392 (19)	0.043 (2)	0.047 (2)	−0.0022 (15)	0.0077 (16)	0.0056 (16)
C23	0.046 (2)	0.050 (2)	0.055 (3)	0.0001 (18)	0.0041 (19)	−0.011 (2)
C24	0.049 (2)	0.082 (3)	0.033 (2)	0.007 (2)	0.0051 (18)	−0.005 (2)
C25	0.040 (2)	0.070 (3)	0.037 (2)	0.0057 (18)	0.0041 (16)	0.0140 (19)
C26	0.058 (3)	0.102 (4)	0.035 (2)	0.011 (2)	0.0101 (19)	0.033 (2)
C27	0.062 (3)	0.084 (3)	0.073 (3)	−0.004 (2)	0.011 (2)	0.050 (3)
C28	0.057 (2)	0.054 (2)	0.063 (3)	−0.0008 (19)	−0.001 (2)	0.032 (2)
C29	0.043 (2)	0.040 (2)	0.046 (2)	−0.0006 (16)	0.0006 (16)	0.0233 (17)
C30	0.0304 (17)	0.047 (2)	0.0392 (19)	0.0060 (15)	0.0030 (15)	0.0161 (16)
C31	0.050 (2)	0.0281 (18)	0.045 (2)	0.0016 (15)	−0.0020 (16)	0.0104 (16)
C32	0.052 (2)	0.065 (3)	0.059 (3)	0.0220 (19)	0.0006 (19)	0.015 (2)
C33	0.084 (3)	0.096 (4)	0.078 (3)	0.054 (3)	0.000 (3)	−0.007 (3)
C34	0.061 (3)	0.072 (3)	0.052 (2)	0.027 (2)	0.004 (2)	−0.003 (2)
O35	0.0536 (16)	0.0537 (16)	0.0576 (17)	−0.0146 (13)	0.0129 (13)	0.0141 (13)
O36	0.108 (2)	0.0271 (13)	0.0595 (18)	−0.0044 (14)	0.0059 (16)	0.0094 (12)
O37	0.0546 (17)	0.131 (3)	0.0481 (17)	0.0014 (17)	0.0128 (14)	0.0447 (18)
O38	0.060 (2)	0.116 (3)	0.099 (3)	0.0102 (19)	0.0011 (18)	0.018 (2)
C39	0.084 (4)	0.146 (5)	0.105 (5)	0.050 (4)	−0.012 (3)	0.030 (4)

Geometric parameters (Å, º)

N1—C2	1.461 (4)	C18—C19	1.376 (6)
N1—C32	1.482 (4)	C18—O38	1.392 (5)
N1—C5	1.487 (4)	C19—C20	1.424 (6)
C2—C21	1.522 (4)	C19—H19	0.9300
C2—C3	1.568 (4)	C20—H20	0.9300
C2—C31	1.589 (4)	C21—C22	1.368 (4)
C3—C13	1.511 (4)	C21—C30	1.411 (5)
C3—C6	1.543 (4)	C22—C23	1.412 (5)
C3—C4	1.563 (4)	C22—H22	0.9300
C4—C14	1.527 (5)	C23—C24	1.370 (5)
C4—C5	1.530 (4)	C23—H23	0.9300
C4—H4	0.9800	C24—C25	1.412 (5)
C5—C34	1.525 (4)	C24—H24	0.9300
C5—H5	0.9800	C25—C30	1.400 (5)
C6—O35	1.214 (4)	C25—C26	1.416 (5)
C6—N7	1.350 (4)	C26—C27	1.369 (6)
N7—C8	1.404 (4)	C26—H26	0.9300
N7—H7	0.8600	C27—C28	1.406 (6)
C8—C9	1.375 (5)	C27—H27	0.9300
C8—C13	1.383 (4)	C28—C29	1.364 (5)
C9—C10	1.377 (5)	C28—H28	0.9300
C9—H9	0.9300	C29—C30	1.402 (4)
C10—C11	1.368 (5)	C29—C31	1.467 (5)
C10—H10	0.9300	C31—O36	1.212 (4)
C11—C12	1.384 (5)	C32—C33	1.514 (5)
C11—H11	0.9300	C32—H32A	0.9700
C12—C13	1.379 (4)	C32—H32B	0.9700
C12—H12	0.9300	C33—C34	1.519 (5)
C14—O37	1.208 (4)	C33—H33A	0.9700
C14—C15	1.486 (5)	C33—H33B	0.9700
C15—C20	1.372 (5)	C34—H34A	0.9700
C15—C16	1.394 (5)	C34—H34B	0.9700
C16—C17	1.363 (5)	O38—C39	1.381 (6)
C16—H16	0.9300	C39—H39A	0.9600
C17—C18	1.355 (6)	C39—H39B	0.9600
C17—H17	0.9300	C39—H39C	0.9600
C2—N1—C32	117.9 (3)	C19—C18—O38	122.7 (5)
C2—N1—C5	109.7 (2)	C18—C19—C20	118.2 (4)
C32—N1—C5	109.2 (2)	C18—C19—H19	120.9
N1—C2—C21	116.0 (2)	C20—C19—H19	120.9
N1—C2—C3	100.9 (2)	C15—C20—C19	120.1 (4)
C21—C2—C3	114.5 (2)	C15—C20—H20	119.9
N1—C2—C31	114.1 (2)	C19—C20—H20	119.9
C21—C2—C31	101.5 (2)	C22—C21—C30	117.8 (3)
C3—C2—C31	110.2 (2)	C22—C21—C2	132.8 (3)
C13—C3—C6	102.0 (2)	C30—C21—C2	109.4 (3)
C13—C3—C4	114.4 (3)	C21—C22—C23	119.4 (3)
C6—C3—C4	117.0 (2)	C21—C22—H22	120.3
C13—C3—C2	113.1 (2)	C23—C22—H22	120.3
C6—C3—C2	110.8 (3)	C24—C23—C22	122.1 (3)
C4—C3—C2	100.0 (2)	C24—C23—H23	119.0
C14—C4—C5	115.1 (3)	C22—C23—H23	119.0
C14—C4—C3	112.1 (3)	C23—C24—C25	120.6 (3)
C5—C4—C3	102.8 (2)	C23—C24—H24	119.7
C14—C4—H4	108.9	C25—C24—H24	119.7
C5—C4—H4	108.9	C30—C25—C24	115.8 (4)
C3—C4—H4	108.9	C30—C25—C26	115.9 (3)
N1—C5—C34	106.0 (3)	C24—C25—C26	128.3 (4)
N1—C5—C4	105.6 (2)	C27—C26—C25	121.1 (4)
C34—C5—C4	118.0 (3)	C27—C26—H26	119.4
N1—C5—H5	109.0	C25—C26—H26	119.4
C34—C5—H5	109.0	C26—C27—C28	122.0 (4)
C4—C5—H5	109.0	C26—C27—H27	119.0
O35—C6—N7	126.0 (3)	C28—C27—H27	119.0
O35—C6—C3	126.5 (3)	C29—C28—C27	118.0 (4)
N7—C6—C3	107.4 (3)	C29—C28—H28	121.0
C6—N7—C8	112.5 (3)	C27—C28—H28	121.0
C6—N7—H7	123.8	C28—C29—C30	120.5 (3)
C8—N7—H7	123.8	C28—C29—C31	131.7 (3)
C9—C8—C13	122.3 (3)	C30—C29—C31	107.8 (3)
C9—C8—N7	128.6 (3)	C25—C30—C29	122.5 (3)
C13—C8—N7	109.1 (3)	C25—C30—C21	124.3 (3)
C8—C9—C10	117.7 (3)	C29—C30—C21	113.2 (3)
C8—C9—H9	121.2	O36—C31—C29	127.7 (3)
C10—C9—H9	121.2	O36—C31—C2	124.3 (3)
C11—C10—C9	121.1 (3)	C29—C31—C2	107.9 (3)
C11—C10—H10	119.4	N1—C32—C33	105.1 (3)
C9—C10—H10	119.4	N1—C32—H32A	110.7
C10—C11—C12	120.8 (4)	C33—C32—H32A	110.7
C10—C11—H11	119.6	N1—C32—H32B	110.7
C12—C11—H11	119.6	C33—C32—H32B	110.7
C13—C12—C11	119.0 (3)	H32A—C32—H32B	108.8
C13—C12—H12	120.5	C32—C33—C34	105.6 (3)
C11—C12—H12	120.5	C32—C33—H33A	110.6
C12—C13—C8	119.2 (3)	C34—C33—H33A	110.6
C12—C13—C3	131.9 (3)	C32—C33—H33B	110.6
C8—C13—C3	108.9 (3)	C34—C33—H33B	110.6
O37—C14—C15	121.0 (3)	H33A—C33—H33B	108.7
O37—C14—C4	120.6 (3)	C33—C34—C5	102.5 (3)
C15—C14—C4	118.3 (3)	C33—C34—H34A	111.3
C20—C15—C16	118.5 (4)	C5—C34—H34A	111.3
C20—C15—C14	119.3 (4)	C33—C34—H34B	111.3
C16—C15—C14	122.2 (4)	C5—C34—H34B	111.3
C17—C16—C15	121.5 (4)	H34A—C34—H34B	109.2
C17—C16—H16	119.2	C39—O38—C18	120.0 (5)
C15—C16—H16	119.2	O38—C39—H39A	109.5
C18—C17—C16	119.7 (5)	O38—C39—H39B	109.5
C18—C17—H17	120.1	H39A—C39—H39B	109.5
C16—C17—H17	120.1	O38—C39—H39C	109.5
C17—C18—C19	121.6 (4)	H39A—C39—H39C	109.5
C17—C18—O38	115.8 (5)	H39B—C39—H39C	109.5
C32—N1—C2—C21	76.1 (4)	C4—C14—C15—C20	153.2 (3)
C5—N1—C2—C21	−158.1 (3)	O37—C14—C15—C16	157.3 (4)
C32—N1—C2—C3	−159.5 (3)	C4—C14—C15—C16	−25.4 (5)
C5—N1—C2—C3	−33.8 (3)	C20—C15—C16—C17	−2.6 (5)
C32—N1—C2—C31	−41.3 (4)	C14—C15—C16—C17	175.9 (3)
C5—N1—C2—C31	84.4 (3)	C15—C16—C17—C18	−1.9 (6)
N1—C2—C3—C13	−77.4 (3)	C16—C17—C18—C19	5.3 (6)
C21—C2—C3—C13	48.0 (4)	C16—C17—C18—O38	−174.7 (3)
C31—C2—C3—C13	161.7 (2)	C17—C18—C19—C20	−4.1 (6)
N1—C2—C3—C6	168.8 (2)	O38—C18—C19—C20	175.9 (3)
C21—C2—C3—C6	−65.8 (3)	C16—C15—C20—C19	3.8 (5)
C31—C2—C3—C6	47.9 (3)	C14—C15—C20—C19	−174.8 (3)
N1—C2—C3—C4	44.7 (3)	C18—C19—C20—C15	−0.6 (6)
C21—C2—C3—C4	170.1 (3)	N1—C2—C21—C22	53.9 (5)
C31—C2—C3—C4	−76.2 (3)	C3—C2—C21—C22	−63.1 (4)
C13—C3—C4—C14	−42.9 (4)	C31—C2—C21—C22	178.2 (3)
C6—C3—C4—C14	76.3 (4)	N1—C2—C21—C30	−128.2 (3)
C2—C3—C4—C14	−164.1 (3)	C3—C2—C21—C30	114.8 (3)
C13—C3—C4—C5	81.3 (3)	C31—C2—C21—C30	−3.9 (3)
C6—C3—C4—C5	−159.5 (3)	C30—C21—C22—C23	−1.6 (4)
C2—C3—C4—C5	−39.9 (3)	C2—C21—C22—C23	176.2 (3)
C2—N1—C5—C34	−117.3 (3)	C21—C22—C23—C24	1.3 (5)
C32—N1—C5—C34	13.3 (4)	C22—C23—C24—C25	−0.5 (6)
C2—N1—C5—C4	8.6 (3)	C23—C24—C25—C30	0.1 (5)
C32—N1—C5—C4	139.2 (3)	C23—C24—C25—C26	−178.1 (4)
C14—C4—C5—N1	142.7 (3)	C30—C25—C26—C27	−0.7 (5)
C3—C4—C5—N1	20.6 (3)	C24—C25—C26—C27	177.5 (4)
C14—C4—C5—C34	−99.1 (4)	C25—C26—C27—C28	1.5 (6)
C3—C4—C5—C34	138.7 (3)	C26—C27—C28—C29	−1.4 (6)
C13—C3—C6—O35	179.9 (3)	C27—C28—C29—C30	0.7 (5)
C4—C3—C6—O35	54.3 (4)	C27—C28—C29—C31	179.8 (3)
C2—C3—C6—O35	−59.5 (4)	C24—C25—C30—C29	−178.5 (3)
C13—C3—C6—N7	−3.1 (3)	C26—C25—C30—C29	−0.1 (5)
C4—C3—C6—N7	−128.7 (3)	C24—C25—C30—C21	−0.5 (5)
C2—C3—C6—N7	117.5 (3)	C26—C25—C30—C21	178.0 (3)
O35—C6—N7—C8	179.1 (3)	C28—C29—C30—C25	0.0 (5)
C3—C6—N7—C8	2.1 (4)	C31—C29—C30—C25	−179.3 (3)
C6—N7—C8—C9	−178.8 (4)	C28—C29—C30—C21	−178.2 (3)
C6—N7—C8—C13	−0.1 (4)	C31—C29—C30—C21	2.5 (4)
C13—C8—C9—C10	0.9 (6)	C22—C21—C30—C25	1.2 (5)
N7—C8—C9—C10	179.5 (3)	C2—C21—C30—C25	−177.1 (3)
C8—C9—C10—C11	−0.6 (6)	C22—C21—C30—C29	179.4 (3)
C9—C10—C11—C12	0.7 (6)	C2—C21—C30—C29	1.2 (4)
C10—C11—C12—C13	−1.0 (6)	C28—C29—C31—O36	−7.7 (6)
C11—C12—C13—C8	1.2 (5)	C30—C29—C31—O36	171.5 (3)
C11—C12—C13—C3	−176.2 (3)	C28—C29—C31—C2	175.9 (3)
C9—C8—C13—C12	−1.1 (5)	C30—C29—C31—C2	−4.9 (3)
N7—C8—C13—C12	−180.0 (3)	N1—C2—C31—O36	−45.7 (4)
C9—C8—C13—C3	176.8 (3)	C21—C2—C31—O36	−171.3 (3)
N7—C8—C13—C3	−2.1 (4)	C3—C2—C31—O36	67.0 (4)
C6—C3—C13—C12	−179.3 (3)	N1—C2—C31—C29	130.8 (3)
C4—C3—C13—C12	−52.0 (4)	C21—C2—C31—C29	5.3 (3)
C2—C3—C13—C12	61.7 (4)	C3—C2—C31—C29	−116.5 (3)
C6—C3—C13—C8	3.1 (3)	C2—N1—C32—C33	134.3 (3)
C4—C3—C13—C8	130.4 (3)	C5—N1—C32—C33	8.3 (4)
C2—C3—C13—C8	−115.9 (3)	N1—C32—C33—C34	−26.8 (5)
C5—C4—C14—O37	−11.8 (5)	C32—C33—C34—C5	34.4 (5)
C3—C4—C14—O37	105.2 (4)	N1—C5—C34—C33	−29.0 (4)
C5—C4—C14—C15	170.9 (3)	C4—C5—C34—C33	−146.9 (4)
C3—C4—C14—C15	−72.1 (4)	C17—C18—O38—C39	−176.5 (4)
O37—C14—C15—C20	−24.1 (5)	C19—C18—O38—C39	3.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O36	0.98	2.40	3.009 (4)	120
C5—H5···O37	0.98	2.40	2.824 (4)	105
C10—H10···O36^i	0.93	2.39	3.301 (5)	165
C26—H26···O37^ii	0.93	2.49	3.375 (5)	159

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