1-Benzoylace­naphthyl­ene-1-spiro-3′-pyrrolizidine-2′-spiro-3′′-1H-indole-2,2′′(1H,3′′H)-dione

The title compound, C₃₂H₂₃ClN₂O₃, crystallizes in the centrosymmetric space group P2₁/n with one mol­ecule in the asymmetric unit. The pyrrolidine rings of the pyrrolizidine moiety adopt envelope conformations. The structure is stabilized by intramolecular C—H...O interactions. The packing is stabilized by N—H...O intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.160
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.00
PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max  Not Given .          ?
PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given .          ?

Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.188
            Value of mu given      =     0.186
CHEMW01_ALERT_1_C  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.99 <> 1.01
            Calculated formula weight =   518.9983
            Formula weight given      =   506.9600
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           506.96
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   32.00  384.35
           H         1.01   23.00   23.18
           N        14.01    2.00   28.01
           O        16.00    3.00   48.00
           Cl       35.45    1.00   35.45
           Calculated formula weight              519.00
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.02
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               5829
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         6155
           Completeness (_total/calc)             94.70%
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     506.96
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C33

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 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, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-Benzoyl-acenaphthylene-1-spiro-3'-pyrrolizidine-2'-spiro-3''- 1H-indole-2,2''(1H,3''H)-dione

Crystal data

C32H23ClN2O3	F(000) = 1056
Mr = 506.96	Dx = 1.324 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5085 (9) Å	Cell parameters from 5762 reflections
b = 9.5986 (8) Å	θ = 2.3–27.8°
c = 23.0306 (18) Å	µ = 0.19 mm^−1
β = 91.232 (1)°	T = 293 K
V = 2543.5 (4) Å^3	Block, colourless
Z = 4	0.21 × 0.20 × 0.20 mm

Data collection

CCD Aread Detector diffractometer	4365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 28.0°, θmin = 1.8°
ω scans	h = −14→15
15033 measured reflections	k = −12→9
5829 independent reflections	l = −29→30

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0961P)^2 + 0.4518P] where P = (Fo^2 + 2Fc^2)/3
5829 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.49 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
Cl1	0.58467 (8)	0.47853 (7)	0.07672 (3)	0.0923 (3)
N1	0.31891 (12)	0.73861 (14)	0.42971 (5)	0.0399 (3)
C2	0.25572 (13)	0.64243 (17)	0.39191 (6)	0.0364 (3)
C3	0.34992 (13)	0.60414 (18)	0.34645 (6)	0.0405 (4)
C4	0.40642 (16)	0.7502 (2)	0.33614 (7)	0.0479 (4)
H4	0.3550	0.8050	0.3105	0.057*
C5	0.40748 (18)	0.8151 (2)	0.39675 (8)	0.0517 (5)
H5	0.4839	0.8001	0.4152	0.062*
C6	0.29528 (15)	0.5359 (2)	0.29125 (7)	0.0487 (4)
N7	0.34923 (15)	0.41263 (19)	0.28397 (6)	0.0574 (4)
H7	0.3334	0.3565	0.2558	0.069*
C8	0.43361 (16)	0.3856 (2)	0.32709 (7)	0.0484 (4)
C9	0.5062 (2)	0.2719 (2)	0.33298 (9)	0.0625 (5)
H9	0.5054	0.2005	0.3057	0.075*
C10	0.58038 (19)	0.2683 (2)	0.38110 (10)	0.0629 (5)
H10	0.6298	0.1925	0.3864	0.075*
C11	0.58259 (16)	0.3743 (2)	0.42131 (9)	0.0574 (5)
H11	0.6323	0.3685	0.4536	0.069*
C12	0.51142 (15)	0.4897 (2)	0.41408 (8)	0.0495 (4)
H12	0.5143	0.5622	0.4408	0.059*
C13	0.43603 (14)	0.49544 (18)	0.36659 (7)	0.0421 (4)
C14	0.52682 (18)	0.7432 (3)	0.30967 (8)	0.0625 (6)
C15	0.53889 (16)	0.6809 (2)	0.25089 (8)	0.0541 (5)
C16	0.63972 (19)	0.6086 (3)	0.23878 (10)	0.0725 (7)
H16	0.6988	0.6030	0.2669	0.087*
C17	0.6539 (2)	0.5448 (3)	0.18571 (11)	0.0755 (7)
H17	0.7213	0.4952	0.1781	0.091*
C18	0.5673 (2)	0.5560 (2)	0.14462 (9)	0.0608 (5)
C19	0.46770 (19)	0.6280 (2)	0.15453 (8)	0.0574 (5)
H19	0.4101	0.6348	0.1257	0.069*
C20	0.45310 (17)	0.6908 (2)	0.20794 (8)	0.0535 (5)
H20	0.3853	0.7400	0.2151	0.064*
C21	0.20194 (13)	0.52053 (16)	0.42374 (6)	0.0349 (3)
C22	0.24517 (15)	0.43008 (18)	0.46471 (7)	0.0412 (4)
H22	0.3229	0.4343	0.4765	0.049*
C23	0.16986 (17)	0.33006 (18)	0.48882 (7)	0.0467 (4)
H23	0.1994	0.2699	0.5171	0.056*
C24	0.05621 (17)	0.31819 (18)	0.47237 (8)	0.0486 (4)
H24	0.0100	0.2500	0.4889	0.058*
C25	0.00842 (15)	0.40937 (18)	0.43021 (7)	0.0445 (4)
C26	−0.10712 (17)	0.4139 (2)	0.40866 (9)	0.0588 (5)
H26	−0.1599	0.3469	0.4206	0.071*
C27	−0.14292 (18)	0.5149 (3)	0.37063 (11)	0.0683 (6)
H27	−0.2200	0.5152	0.3577	0.082*
C28	−0.06787 (17)	0.6184 (2)	0.35024 (9)	0.0594 (5)
H28	−0.0946	0.6874	0.3249	0.071*
C29	0.04601 (15)	0.61456 (19)	0.36881 (7)	0.0440 (4)
C30	0.08329 (14)	0.51003 (16)	0.40771 (6)	0.0379 (3)
C31	0.14544 (15)	0.70743 (19)	0.35959 (6)	0.0431 (4)
C32	0.3748 (3)	0.9681 (2)	0.40221 (11)	0.0796 (7)
H32A	0.3199	0.9958	0.3718	0.096*
H32B	0.4429	1.0275	0.4008	0.096*
C33	0.3198 (3)	0.9727 (2)	0.46178 (12)	0.0816 (8)
H33A	0.3788	0.9765	0.4925	0.098*
H33B	0.2689	1.0527	0.4652	0.098*
C34	0.25176 (18)	0.83813 (19)	0.46427 (8)	0.0510 (4)
H34A	0.2455	0.8061	0.5040	0.061*
H34B	0.1742	0.8503	0.4477	0.061*
O35	0.21838 (12)	0.5840 (2)	0.26043 (5)	0.0671 (4)
O36	0.61161 (15)	0.7849 (3)	0.33588 (8)	0.1074 (8)
O37	0.14390 (12)	0.81920 (15)	0.33534 (6)	0.0581 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1321 (7)	0.0769 (4)	0.0695 (4)	−0.0004 (4)	0.0374 (4)	−0.0141 (3)
N1	0.0430 (7)	0.0427 (7)	0.0341 (6)	−0.0055 (6)	0.0050 (5)	−0.0011 (5)
C2	0.0347 (8)	0.0441 (8)	0.0304 (6)	−0.0017 (6)	0.0025 (6)	0.0021 (6)
C3	0.0345 (8)	0.0580 (10)	0.0291 (7)	−0.0076 (7)	0.0028 (6)	−0.0034 (6)
C4	0.0441 (9)	0.0619 (11)	0.0378 (8)	−0.0130 (8)	0.0060 (7)	0.0019 (7)
C5	0.0532 (11)	0.0577 (11)	0.0445 (9)	−0.0192 (9)	0.0081 (8)	−0.0022 (8)
C6	0.0411 (9)	0.0762 (13)	0.0290 (7)	−0.0136 (9)	0.0044 (7)	−0.0056 (7)
N7	0.0639 (10)	0.0707 (11)	0.0374 (7)	−0.0161 (9)	0.0000 (7)	−0.0179 (7)
C8	0.0478 (10)	0.0571 (11)	0.0407 (8)	−0.0123 (8)	0.0083 (7)	−0.0108 (7)
C9	0.0711 (13)	0.0545 (12)	0.0625 (11)	−0.0066 (10)	0.0139 (10)	−0.0173 (9)
C10	0.0510 (11)	0.0589 (12)	0.0792 (14)	0.0047 (9)	0.0080 (10)	−0.0032 (10)
C11	0.0361 (9)	0.0709 (13)	0.0650 (11)	0.0021 (9)	−0.0041 (8)	−0.0073 (10)
C12	0.0365 (9)	0.0641 (11)	0.0479 (9)	0.0000 (8)	−0.0004 (7)	−0.0145 (8)
C13	0.0324 (8)	0.0559 (10)	0.0381 (8)	−0.0066 (7)	0.0067 (6)	−0.0090 (7)
C14	0.0497 (11)	0.0931 (16)	0.0450 (9)	−0.0254 (11)	0.0092 (8)	0.0010 (10)
C15	0.0450 (10)	0.0741 (13)	0.0439 (9)	−0.0107 (9)	0.0128 (8)	0.0087 (8)
C16	0.0490 (12)	0.109 (2)	0.0596 (12)	0.0017 (12)	0.0059 (10)	0.0112 (12)
C17	0.0645 (14)	0.0874 (17)	0.0755 (15)	0.0128 (12)	0.0221 (12)	0.0052 (13)
C18	0.0769 (14)	0.0553 (11)	0.0510 (10)	−0.0055 (10)	0.0224 (10)	0.0059 (8)
C19	0.0628 (12)	0.0695 (13)	0.0403 (9)	−0.0056 (10)	0.0096 (8)	0.0096 (8)
C20	0.0494 (10)	0.0688 (12)	0.0430 (9)	−0.0008 (9)	0.0129 (8)	0.0099 (8)
C21	0.0346 (8)	0.0405 (8)	0.0298 (6)	0.0001 (6)	0.0042 (6)	−0.0018 (6)
C22	0.0425 (9)	0.0446 (9)	0.0364 (7)	0.0015 (7)	−0.0006 (6)	0.0012 (6)
C23	0.0589 (11)	0.0393 (9)	0.0419 (8)	0.0037 (8)	0.0041 (8)	0.0055 (7)
C24	0.0556 (11)	0.0399 (9)	0.0506 (9)	−0.0072 (8)	0.0110 (8)	0.0014 (7)
C25	0.0421 (9)	0.0459 (9)	0.0460 (8)	−0.0057 (7)	0.0092 (7)	−0.0057 (7)
C26	0.0413 (10)	0.0681 (13)	0.0672 (12)	−0.0121 (9)	0.0057 (9)	0.0003 (10)
C27	0.0338 (10)	0.0941 (17)	0.0767 (14)	−0.0067 (10)	−0.0083 (10)	0.0053 (12)
C28	0.0440 (10)	0.0776 (14)	0.0562 (10)	0.0042 (9)	−0.0084 (8)	0.0115 (10)
C29	0.0376 (9)	0.0563 (10)	0.0381 (7)	0.0013 (7)	0.0005 (6)	0.0039 (7)
C30	0.0356 (8)	0.0437 (8)	0.0343 (7)	0.0008 (6)	0.0033 (6)	−0.0030 (6)
C31	0.0435 (9)	0.0537 (10)	0.0323 (7)	0.0024 (7)	0.0029 (6)	0.0080 (7)
C32	0.113 (2)	0.0510 (12)	0.0757 (14)	−0.0271 (13)	0.0254 (14)	−0.0013 (10)
C33	0.116 (2)	0.0512 (12)	0.0790 (15)	−0.0122 (13)	0.0249 (14)	−0.0133 (11)
C34	0.0607 (12)	0.0465 (10)	0.0459 (9)	0.0034 (8)	0.0081 (8)	−0.0041 (7)
O35	0.0501 (8)	0.1151 (13)	0.0358 (6)	−0.0034 (8)	−0.0069 (6)	−0.0060 (7)
O36	0.0606 (10)	0.195 (2)	0.0676 (10)	−0.0584 (13)	0.0156 (8)	−0.0300 (12)
O37	0.0631 (9)	0.0611 (8)	0.0503 (7)	0.0028 (6)	0.0018 (6)	0.0228 (6)

Geometric parameters (Å, º)

Cl1—C18	1.747 (2)	C16—H16	0.9300
N1—C2	1.453 (2)	C17—C18	1.364 (3)
N1—C34	1.473 (2)	C17—H17	0.9300
N1—C5	1.479 (2)	C18—C19	1.362 (3)
C2—C21	1.520 (2)	C19—C20	1.383 (3)
C2—C3	1.567 (2)	C19—H19	0.9300
C2—C31	1.585 (2)	C20—H20	0.9300
C3—C13	1.505 (2)	C21—C22	1.368 (2)
C3—C6	1.551 (2)	C21—C30	1.410 (2)
C3—C4	1.566 (2)	C22—C23	1.415 (2)
C4—C14	1.527 (3)	C22—H22	0.9300
C4—C5	1.528 (2)	C23—C24	1.359 (3)
C4—H4	0.9800	C23—H23	0.9300
C5—C32	1.522 (3)	C24—C25	1.410 (3)
C5—H5	0.9800	C24—H24	0.9300
C6—O35	1.214 (2)	C25—C30	1.401 (2)
C6—N7	1.348 (3)	C25—C26	1.410 (3)
N7—C8	1.398 (2)	C26—C27	1.364 (3)
N7—H7	0.8600	C26—H26	0.9300
C8—C9	1.380 (3)	C27—C28	1.404 (3)
C8—C13	1.392 (2)	C27—H27	0.9300
C9—C10	1.385 (3)	C28—C29	1.370 (3)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.376 (3)	C29—C30	1.406 (2)
C10—H10	0.9300	C29—C31	1.470 (2)
C11—C12	1.385 (3)	C31—O37	1.210 (2)
C11—H11	0.9300	C32—C33	1.524 (3)
C12—C13	1.383 (3)	C32—H32A	0.9700
C12—H12	0.9300	C32—H32B	0.9700
C14—O36	1.205 (2)	C33—C34	1.512 (3)
C14—C15	1.489 (3)	C33—H33A	0.9700
C15—C16	1.386 (3)	C33—H33B	0.9700
C15—C20	1.386 (3)	C34—H34A	0.9700
C16—C17	1.380 (3)	C34—H34B	0.9700
C2—N1—C34	118.3 (1)	C16—C17—H17	120.6
C2—N1—C5	110.4 (1)	C19—C18—C17	121.9 (2)
C34—N1—C5	109.3 (1)	C19—C18—Cl1	118.61 (18)
N1—C2—C21	113.82 (12)	C17—C18—Cl1	119.44 (18)
N1—C2—C3	101.82 (12)	C18—C19—C20	119.3 (2)
C21—C2—C3	115.89 (13)	C18—C19—H19	120.4
N1—C2—C31	114.61 (13)	C20—C19—H19	120.4
C21—C2—C31	101.49 (12)	C19—C20—C15	120.43 (19)
C3—C2—C31	109.70 (12)	C19—C20—H20	119.8
C13—C3—C6	102.26 (14)	C15—C20—H20	119.8
C13—C3—C4	113.24 (14)	C22—C21—C30	118.09 (14)
C6—C3—C4	114.60 (13)	C22—C21—C2	132.50 (15)
C13—C3—C2	114.65 (12)	C30—C21—C2	109.32 (13)
C6—C3—C2	111.87 (13)	C21—C22—C23	118.98 (16)
C4—C3—C2	100.77 (13)	C21—C22—H22	120.5
C14—C4—C5	113.15 (15)	C23—C22—H22	120.5
C14—C4—C3	113.86 (17)	C24—C23—C22	122.80 (16)
C5—C4—C3	102.79 (13)	C24—C23—H23	118.6
C14—C4—H4	108.9	C22—C23—H23	118.6
C5—C4—H4	108.9	C23—C24—C25	119.92 (16)
C3—C4—H4	108.9	C23—C24—H24	120.0
N1—C5—C32	105.20 (16)	C25—C24—H24	120.0
N1—C5—C4	105.95 (14)	C30—C25—C26	115.54 (17)
C32—C5—C4	118.12 (18)	C30—C25—C24	116.67 (16)
N1—C5—H5	109.1	C26—C25—C24	127.77 (17)
C32—C5—H5	109.1	C27—C26—C25	121.16 (18)
C4—C5—H5	109.1	C27—C26—H26	119.4
O35—C6—N7	126.40 (17)	C25—C26—H26	119.4
O35—C6—C3	126.58 (19)	C26—C27—C28	122.56 (18)
N7—C6—C3	107.02 (15)	C26—C27—H27	118.7
C6—N7—C8	112.9 (1)	C28—C27—H27	118.7
C6—N7—H7	123.6	C29—C28—C27	117.89 (18)
C8—N7—H7	123.6	C29—C28—H28	121.1
C9—C8—C13	122.1 (2)	C27—C28—H28	121.1
C9—C8—N7	128.78 (17)	C28—C29—C30	119.65 (17)
C13—C8—N7	109.12 (17)	C28—C29—C31	132.93 (17)
C8—C9—C10	117.4 (2)	C30—C29—C31	107.27 (14)
C8—C9—H9	121.3	C25—C30—C29	123.10 (16)
C10—C9—H9	121.3	C25—C30—C21	123.50 (15)
C11—C10—C9	121.5 (2)	C29—C30—C21	113.35 (14)
C11—C10—H10	119.2	O37—C31—C29	126.94 (16)
C9—C10—H10	119.2	O37—C31—C2	124.72 (16)
C10—C11—C12	120.5 (2)	C29—C31—C2	108.15 (13)
C10—C11—H11	119.7	C5—C32—C33	102.16 (18)
C12—C11—H11	119.7	C5—C32—H32A	111.3
C13—C12—C11	119.1 (2)	C33—C32—H32A	111.3
C13—C12—H12	120.4	C5—C32—H32B	111.3
C11—C12—H12	120.4	C33—C32—H32B	111.3
C12—C13—C8	119.33 (17)	H32A—C32—H32B	109.2
C12—C13—C3	132.02 (15)	C34—C33—C32	103.57 (18)
C8—C13—C3	108.64 (15)	C34—C33—H33A	111.0
O36—C14—C15	119.90 (19)	C32—C33—H33A	111.0
O36—C14—C4	121.16 (18)	C34—C33—H33B	111.0
C15—C14—C4	118.93 (16)	C32—C33—H33B	111.0
C16—C15—C20	118.52 (19)	H33A—C33—H33B	109.0
C16—C15—C14	118.62 (19)	N1—C34—C33	104.80 (16)
C20—C15—C14	122.85 (18)	N1—C34—H34A	110.8
C17—C16—C15	121.1 (2)	C33—C34—H34A	110.8
C17—C16—H16	119.5	N1—C34—H34B	110.8
C15—C16—H16	119.5	C33—C34—H34B	110.8
C18—C17—C16	118.7 (2)	H34A—C34—H34B	108.9
C18—C17—H17	120.6
C34—N1—C2—C21	−77.33 (18)	O36—C14—C15—C16	32.1 (3)
C5—N1—C2—C21	155.66 (14)	C4—C14—C15—C16	−146.6 (2)
C34—N1—C2—C3	157.22 (14)	O36—C14—C15—C20	−148.6 (3)
C5—N1—C2—C3	30.22 (17)	C4—C14—C15—C20	32.7 (3)
C34—N1—C2—C31	38.89 (18)	C20—C15—C16—C17	−1.5 (3)
C5—N1—C2—C31	−88.12 (16)	C14—C15—C16—C17	177.8 (2)
N1—C2—C3—C13	80.47 (15)	C15—C16—C17—C18	1.1 (4)
C21—C2—C3—C13	−43.60 (18)	C16—C17—C18—C19	0.0 (4)
C31—C2—C3—C13	−157.74 (14)	C16—C17—C18—Cl1	178.90 (19)
N1—C2—C3—C6	−163.68 (14)	C17—C18—C19—C20	−0.6 (3)
C21—C2—C3—C6	72.25 (18)	Cl1—C18—C19—C20	−179.49 (15)
C31—C2—C3—C6	−41.89 (19)	C18—C19—C20—C15	0.1 (3)
N1—C2—C3—C4	−41.48 (14)	C16—C15—C20—C19	0.9 (3)
C21—C2—C3—C4	−165.55 (13)	C14—C15—C20—C19	−178.39 (19)
C31—C2—C3—C4	80.31 (15)	N1—C2—C21—C22	−47.8 (2)
C13—C3—C4—C14	37.80 (19)	C3—C2—C21—C22	69.7 (2)
C6—C3—C4—C14	−78.99 (19)	C31—C2—C21—C22	−171.50 (16)
C2—C3—C4—C14	160.74 (14)	N1—C2—C21—C30	128.53 (14)
C13—C3—C4—C5	−84.96 (16)	C3—C2—C21—C30	−113.88 (14)
C6—C3—C4—C5	158.25 (15)	C31—C2—C21—C30	4.87 (15)
C2—C3—C4—C5	37.98 (16)	C30—C21—C22—C23	0.4 (2)
C2—N1—C5—C32	119.82 (18)	C2—C21—C22—C23	176.50 (15)
C34—N1—C5—C32	−12.0 (2)	C21—C22—C23—C24	1.1 (3)
C2—N1—C5—C4	−6.0 (2)	C22—C23—C24—C25	−1.0 (3)
C34—N1—C5—C4	−137.86 (16)	C23—C24—C25—C30	−0.5 (2)
C14—C4—C5—N1	−144.13 (17)	C23—C24—C25—C26	−178.92 (19)
C3—C4—C5—N1	−20.89 (19)	C30—C25—C26—C27	−3.1 (3)
C14—C4—C5—C32	98.4 (2)	C24—C25—C26—C27	175.3 (2)
C3—C4—C5—C32	−138.40 (19)	C25—C26—C27—C28	0.7 (4)
C13—C3—C6—O35	178.22 (17)	C26—C27—C28—C29	1.4 (4)
C4—C3—C6—O35	−58.9 (2)	C27—C28—C29—C30	−0.9 (3)
C2—C3—C6—O35	55.1 (2)	C27—C28—C29—C31	−176.0 (2)
C13—C3—C6—N7	−1.67 (16)	C26—C25—C30—C29	3.6 (2)
C4—C3—C6—N7	121.26 (16)	C24—C25—C30—C29	−175.00 (15)
C2—C3—C6—N7	−124.84 (15)	C26—C25—C30—C21	−179.36 (16)
O35—C6—N7—C8	−179.43 (17)	C24—C25—C30—C21	2.0 (2)
C3—C6—N7—C8	0.46 (19)	C28—C29—C30—C25	−1.7 (3)
C6—N7—C8—C9	−178.98 (18)	C31—C29—C30—C25	174.57 (15)
C6—N7—C8—C13	1.1 (2)	C28—C29—C30—C21	−178.97 (16)
C13—C8—C9—C10	1.9 (3)	C31—C29—C30—C21	−2.74 (19)
N7—C8—C9—C10	−178.04 (18)	C22—C21—C30—C25	−2.0 (2)
C8—C9—C10—C11	−0.5 (3)	C2—C21—C30—C25	−178.95 (14)
C9—C10—C11—C12	−1.2 (3)	C22—C21—C30—C29	175.32 (14)
C10—C11—C12—C13	1.5 (3)	C2—C21—C30—C29	−1.65 (18)
C11—C12—C13—C8	−0.2 (3)	C28—C29—C31—O37	6.2 (3)
C11—C12—C13—C3	−179.46 (17)	C30—C29—C31—O37	−169.34 (17)
C9—C8—C13—C12	−1.5 (3)	C28—C29—C31—C2	−178.67 (19)
N7—C8—C13—C12	178.39 (16)	C30—C29—C31—C2	5.81 (18)
C9—C8—C13—C3	177.88 (16)	N1—C2—C31—O37	45.7 (2)
N7—C8—C13—C3	−2.18 (19)	C21—C2—C31—O37	168.84 (16)
C6—C3—C13—C12	−178.36 (18)	C3—C2—C31—O37	−68.1 (2)
C4—C3—C13—C12	57.8 (2)	N1—C2—C31—C29	−129.57 (14)
C2—C3—C13—C12	−57.1 (2)	C21—C2—C31—C29	−6.45 (16)
C6—C3—C13—C8	2.31 (16)	C3—C2—C31—C29	116.65 (14)
C4—C3—C13—C8	−121.53 (15)	N1—C5—C32—C33	31.2 (2)
C2—C3—C13—C8	123.59 (15)	C4—C5—C32—C33	149.1 (2)
C5—C4—C14—O36	0.6 (3)	C5—C32—C33—C34	−38.7 (3)
C3—C4—C14—O36	−116.3 (3)	C2—N1—C34—C33	−139.96 (17)
C5—C4—C14—C15	179.34 (18)	C5—N1—C34—C33	−12.4 (2)
C3—C4—C14—C15	62.4 (2)	C32—C33—C34—N1	31.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O37	0.98	2.51	3.093 (2)	118
C5—H5···O36	0.98	2.37	2.777 (3)	104
N7—H7···O37^i	0.86	2.15	2.893 (2)	144

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.