5-(2-Chloro­phenyl)-7,7-dimethyl-10-(4-methyl­phenyl)-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione dimethyl­formamide solvate

Jiang, H.; Wang, X.-S.; Zhang, M.-M.; Yao, C.-S.; Tu, S.-J.

doi:10.1107/S1600536806046952

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5-(2-Chlorophenyl)-7,7-dimethyl-10-(4-methylphenyl)-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione dimethylformamide solvate

H. Jiang, X.-S. Wang, M.-M. Zhang, C.-S. Yao and S.-J. Tu

The title compound, C₃₁H₂₆ClNO₂·C₃H₇NO, was synthesized by the reaction of 2-chlorobenzaldehyde, 5,5-dimethyl-3-(4-methylanilino)cyclohex-2-enone and 1,3-indenedione in an ionic liquid medium. The 1,4-dihydropyridine ring adopts a boat conformation, while the cyclohexenone ring adopts an envelope conformation. In the crystal structure, C—H

O hydrogen bonds link the indeno[1,2-b]quinoline molecules and the dimethylformamide solvent molecules to form a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046952/sj2146sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046952/sj2146Isup2.hkl Contains datablock I

CCDC reference: 609556

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.004 Å
R factor = 0.062
wR factor = 0.158
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.688     0.974
            Tmin(prime) and Tmax expected:      0.886     0.974
            RR(prime) =      0.776
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.31

   0 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

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

5-(2-Chlorophenyl)-7,7-dimethyl-10-(4-methylphenyl)-7,8-dihydro-5H- indeno[1,2-b]quinoline-9,11(6H,10H)-dione dimethylformamide solvate top

Crystal data top

C₃₁H₂₆ClNO₂·C₃H₇NO	Z = 2
M_r = 553.07	F(000) = 584
Triclinic, P1	D_x = 1.315 Mg m⁻³
Hall symbol: -P 1	Melting point = 536–538 K
a = 10.872 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 11.655 (2) Å	Cell parameters from 5152 reflections
c = 11.689 (2) Å	θ = 3.0–25.3°
α = 92.100 (4)°	µ = 0.18 mm⁻¹
β = 99.730 (4)°	T = 153 K
γ = 106.147 (4)°	Block, red
V = 1396.8 (4) Å³	0.68 × 0.23 × 0.15 mm

Data collection top

Rigaku Mercury diffractometer	5071 independent reflections
Radiation source: fine-focus sealed tube	4222 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.0°
ω scans	h = −13→13
Absorption correction: multi-scan (Jacobson, 1998)	k = −12→14
T_min = 0.688, T_max = 0.974	l = −14→14
13755 measured reflections

Refinement top

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0722P)² + 1.2467P] where P = (F_o² + 2F_c²)/3
5071 reflections	(Δ/σ)_max < 0.001
367 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

Experimental. Elemental analysis, calculated: C 73.83, H 6.01, N 5.06%; found: C 73.89, H 5.90, N 5.01%. Spectroscopic analysis: ¹H NMR (DMSO-d₆, δ, p.p.m.): 0.83 (s, 3H, CH₃), 0.93 (s, 3H, CH₃), 2.00 (d, J = 16.8 Hz, 2H, 2CH), 2.24 (d, J = 16.4 Hz, 1H, CH), 2.36 (d, J = 17.6 Hz, 1H, CH), 2.50 (s, 3H, CH₃), 2.74 (s, 3H, CH₃), 2.89 (s, 3H, CH₃), 5.18 (d, J = 7.6 Hz, 1H, ArH), 5.24 (s, 1H, CH), 6.98–7.03 (m, 1H, ArH), 7.13–7.20 (m, 3H, ArH), 7.25–7.32 (m, 2H, ArH), 7.49–7.58 (m, 5H, ArH), 7.96 (s, 1H, CHO); IR (Medium?, ν, cm^-1): 3059 (ArH), 2957, 2933, 2857 (C—H), 1673, 1644 (C═ O), 1590, 1558, 1511, 1456, 1439 (benzene ring).

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.93127 (7)	0.33089 (7)	0.46385 (6)	0.0358 (2)
O1	0.64581 (18)	0.23371 (18)	0.59852 (17)	0.0334 (5)
O2	0.83587 (17)	0.56520 (17)	0.29727 (18)	0.0322 (5)
O3	0.2632 (3)	1.0365 (2)	0.0912 (2)	0.0625 (8)
N1	0.3900 (2)	0.38083 (19)	0.30245 (19)	0.0234 (5)
N2	0.1258 (3)	0.8918 (2)	0.1689 (2)	0.0365 (6)
C1	0.4059 (2)	0.3141 (2)	0.3997 (2)	0.0227 (6)
C2	0.5245 (2)	0.3047 (2)	0.4479 (2)	0.0222 (6)
C3	0.6471 (2)	0.3554 (2)	0.3987 (2)	0.0227 (6)
H3	0.7205	0.3960	0.4640	0.027*
C4	0.6215 (2)	0.4466 (2)	0.3173 (2)	0.0224 (6)
C5	0.5000 (2)	0.4502 (2)	0.2691 (2)	0.0218 (5)
C6	0.5387 (3)	0.2415 (2)	0.5540 (2)	0.0237 (6)
C7	0.4204 (3)	0.1914 (2)	0.6075 (2)	0.0269 (6)
H7A	0.4157	0.2525	0.6663	0.032*
H7B	0.4309	0.1209	0.6485	0.032*
C8	0.2922 (3)	0.1537 (2)	0.5198 (2)	0.0257 (6)
C9	0.2847 (3)	0.2586 (2)	0.4465 (2)	0.0260 (6)
H9A	0.2106	0.2300	0.3803	0.031*
H9B	0.2663	0.3212	0.4948	0.031*
C10	0.2867 (3)	0.0432 (3)	0.4422 (3)	0.0403 (7)
H10A	0.3590	0.0626	0.3994	0.061*
H10B	0.2038	0.0184	0.3868	0.061*
H10C	0.2940	−0.0224	0.4906	0.061*
C11	0.1758 (3)	0.1252 (3)	0.5824 (3)	0.0327 (7)
H11A	0.1790	0.0587	0.6306	0.049*
H11B	0.0946	0.1027	0.5247	0.049*
H11C	0.1794	0.1961	0.6321	0.049*
C12	0.7169 (2)	0.5381 (2)	0.2706 (2)	0.0230 (6)
C13	0.6401 (2)	0.5963 (2)	0.1849 (2)	0.0223 (6)
C14	0.6831 (3)	0.6895 (2)	0.1196 (2)	0.0273 (6)
H14	0.7737	0.7252	0.1227	0.033*
C15	0.5904 (3)	0.7306 (3)	0.0482 (2)	0.0306 (6)
H15	0.6176	0.7957	0.0029	0.037*
C16	0.4598 (3)	0.6765 (3)	0.0438 (3)	0.0329 (7)
H16	0.3977	0.7044	−0.0060	0.039*
C17	0.4156 (3)	0.5814 (2)	0.1107 (2)	0.0287 (6)
H17	0.3250	0.5449	0.1065	0.034*
C18	0.5066 (2)	0.5424 (2)	0.1825 (2)	0.0226 (5)
C19	0.6853 (3)	0.2587 (2)	0.3328 (2)	0.0245 (6)
C20	0.8103 (3)	0.2455 (2)	0.3522 (2)	0.0279 (6)
C21	0.8433 (3)	0.1634 (3)	0.2831 (3)	0.0352 (7)
H21	0.9296	0.1568	0.2972	0.042*
C22	0.7516 (3)	0.0916 (3)	0.1944 (3)	0.0385 (7)
H22	0.7747	0.0366	0.1463	0.046*
C23	0.6248 (3)	0.1000 (3)	0.1756 (3)	0.0365 (7)
H23	0.5603	0.0490	0.1160	0.044*
C24	0.5928 (3)	0.1826 (2)	0.2438 (2)	0.0295 (6)
H24	0.5060	0.1879	0.2300	0.035*
C25	0.2614 (2)	0.3835 (2)	0.2466 (2)	0.0210 (5)
C26	0.2064 (2)	0.4663 (2)	0.2876 (2)	0.0235 (6)
H26	0.2524	0.5219	0.3526	0.028*
C27	0.0833 (3)	0.4677 (2)	0.2331 (2)	0.0256 (6)
H27	0.0449	0.5241	0.2617	0.031*
C28	0.0154 (2)	0.3881 (2)	0.1377 (2)	0.0251 (6)
C29	0.0727 (3)	0.3048 (2)	0.0989 (2)	0.0266 (6)
H29	0.0269	0.2492	0.0339	0.032*
C30	0.1951 (2)	0.3011 (2)	0.1528 (2)	0.0234 (6)
H30	0.2327	0.2431	0.1260	0.028*
C31	−0.1181 (3)	0.3900 (3)	0.0782 (3)	0.0352 (7)
H31A	−0.1830	0.3488	0.1231	0.053*
H31B	−0.1382	0.3492	−0.0004	0.053*
H31C	−0.1200	0.4733	0.0731	0.053*
C32	0.2359 (4)	0.9391 (3)	0.1391 (3)	0.0496 (9)
H32	0.3009	0.8987	0.1539	0.059*
C33	0.0236 (4)	0.9551 (3)	0.1574 (3)	0.0505 (9)
H33A	0.0596	1.0366	0.1361	0.076*
H33B	−0.0059	0.9591	0.2318	0.076*
H33C	−0.0503	0.9115	0.0968	0.076*
C34	0.0943 (3)	0.7840 (3)	0.2262 (3)	0.0408 (8)
H34A	0.1684	0.7506	0.2362	0.061*
H34B	0.0179	0.7257	0.1789	0.061*
H34C	0.0750	0.8019	0.3027	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0233 (4)	0.0461 (5)	0.0382 (4)	0.0104 (3)	0.0047 (3)	0.0101 (3)
O1	0.0262 (11)	0.0430 (12)	0.0324 (11)	0.0129 (9)	0.0029 (9)	0.0110 (9)
O2	0.0177 (10)	0.0342 (11)	0.0446 (12)	0.0054 (8)	0.0082 (8)	0.0082 (9)
O3	0.0813 (19)	0.0345 (13)	0.0727 (18)	−0.0023 (13)	0.0478 (15)	0.0109 (12)
N1	0.0166 (11)	0.0275 (12)	0.0249 (11)	0.0031 (9)	0.0045 (9)	0.0091 (9)
N2	0.0425 (15)	0.0283 (13)	0.0308 (13)	−0.0017 (11)	0.0038 (11)	0.0080 (10)
C1	0.0228 (13)	0.0229 (13)	0.0213 (13)	0.0040 (10)	0.0052 (11)	0.0030 (10)
C2	0.0201 (13)	0.0245 (13)	0.0215 (13)	0.0051 (10)	0.0045 (10)	0.0022 (10)
C3	0.0168 (12)	0.0270 (14)	0.0231 (13)	0.0050 (10)	0.0027 (10)	0.0027 (10)
C4	0.0186 (13)	0.0220 (13)	0.0260 (14)	0.0044 (10)	0.0048 (11)	0.0001 (10)
C5	0.0200 (13)	0.0225 (13)	0.0220 (13)	0.0037 (10)	0.0061 (10)	0.0011 (10)
C6	0.0263 (14)	0.0231 (13)	0.0210 (13)	0.0069 (11)	0.0035 (11)	−0.0014 (10)
C7	0.0299 (15)	0.0292 (15)	0.0215 (13)	0.0070 (12)	0.0062 (11)	0.0067 (11)
C8	0.0263 (14)	0.0235 (14)	0.0255 (14)	0.0035 (11)	0.0055 (11)	0.0049 (11)
C9	0.0214 (13)	0.0287 (14)	0.0278 (14)	0.0045 (11)	0.0073 (11)	0.0112 (11)
C10	0.0449 (18)	0.0300 (16)	0.0417 (18)	0.0027 (14)	0.0112 (15)	−0.0043 (13)
C11	0.0311 (15)	0.0328 (16)	0.0330 (16)	0.0035 (13)	0.0107 (13)	0.0111 (12)
C12	0.0207 (14)	0.0238 (13)	0.0255 (14)	0.0056 (11)	0.0085 (11)	0.0000 (10)
C13	0.0218 (13)	0.0211 (13)	0.0247 (13)	0.0050 (10)	0.0080 (11)	0.0018 (10)
C14	0.0240 (14)	0.0267 (14)	0.0306 (15)	0.0030 (11)	0.0110 (12)	0.0024 (11)
C15	0.0324 (15)	0.0308 (15)	0.0295 (15)	0.0059 (12)	0.0120 (12)	0.0110 (12)
C16	0.0275 (15)	0.0359 (16)	0.0359 (16)	0.0081 (13)	0.0068 (13)	0.0150 (13)
C17	0.0203 (13)	0.0318 (15)	0.0330 (15)	0.0041 (11)	0.0063 (12)	0.0094 (12)
C18	0.0215 (13)	0.0219 (13)	0.0242 (13)	0.0044 (10)	0.0072 (11)	0.0012 (10)
C19	0.0262 (14)	0.0281 (14)	0.0222 (13)	0.0097 (11)	0.0082 (11)	0.0097 (11)
C20	0.0304 (15)	0.0291 (15)	0.0276 (14)	0.0104 (12)	0.0096 (12)	0.0129 (11)
C21	0.0397 (17)	0.0378 (17)	0.0411 (17)	0.0223 (14)	0.0214 (14)	0.0179 (14)
C22	0.058 (2)	0.0336 (17)	0.0371 (17)	0.0245 (15)	0.0251 (16)	0.0115 (13)
C23	0.0497 (19)	0.0315 (16)	0.0294 (15)	0.0123 (14)	0.0092 (14)	0.0048 (12)
C24	0.0326 (15)	0.0292 (15)	0.0293 (15)	0.0110 (12)	0.0093 (12)	0.0054 (12)
C25	0.0154 (12)	0.0234 (13)	0.0234 (13)	0.0024 (10)	0.0052 (10)	0.0095 (10)
C26	0.0231 (13)	0.0226 (13)	0.0226 (13)	0.0026 (11)	0.0052 (11)	0.0015 (10)
C27	0.0269 (14)	0.0243 (14)	0.0303 (15)	0.0097 (11)	0.0129 (12)	0.0089 (11)
C28	0.0226 (13)	0.0283 (14)	0.0262 (14)	0.0066 (11)	0.0088 (11)	0.0123 (11)
C29	0.0259 (14)	0.0290 (15)	0.0213 (13)	0.0026 (11)	0.0032 (11)	0.0026 (11)
C30	0.0233 (13)	0.0238 (14)	0.0255 (14)	0.0077 (11)	0.0091 (11)	0.0049 (11)
C31	0.0242 (15)	0.0481 (18)	0.0356 (16)	0.0130 (13)	0.0052 (12)	0.0145 (14)
C32	0.050 (2)	0.049 (2)	0.046 (2)	0.0066 (17)	0.0124 (17)	−0.0034 (16)
C33	0.050 (2)	0.046 (2)	0.059 (2)	0.0168 (17)	0.0156 (18)	0.0071 (17)
C34	0.0344 (17)	0.0408 (18)	0.0375 (17)	−0.0019 (14)	0.0000 (14)	0.0118 (14)

Geometric parameters (Å, º) top

Cl1—C20	1.738 (3)	C14—H14	0.9500
O1—C6	1.222 (3)	C15—C16	1.375 (4)
O2—C12	1.224 (3)	C15—H15	0.9500
O3—C32	1.267 (4)	C16—C17	1.402 (4)
N1—C5	1.371 (3)	C16—H16	0.9500
N1—C1	1.414 (3)	C17—C18	1.374 (4)
N1—C25	1.449 (3)	C17—H17	0.9500
N2—C32	1.283 (4)	C19—C20	1.392 (4)
N2—C34	1.429 (4)	C19—C24	1.401 (4)
N2—C33	1.487 (4)	C20—C21	1.389 (4)
C1—C2	1.354 (4)	C21—C22	1.376 (5)
C1—C9	1.500 (4)	C21—H21	0.9500
C2—C6	1.472 (4)	C22—C23	1.389 (4)
C2—C3	1.517 (3)	C22—H22	0.9500
C3—C4	1.505 (4)	C23—C24	1.381 (4)
C3—C19	1.529 (4)	C23—H23	0.9500
C3—H3	1.0000	C24—H24	0.9500
C4—C5	1.358 (4)	C25—C26	1.380 (4)
C4—C12	1.459 (4)	C25—C30	1.384 (4)
C5—C18	1.499 (4)	C26—C27	1.386 (4)
C6—C7	1.507 (4)	C26—H26	0.9500
C7—C8	1.526 (4)	C27—C28	1.383 (4)
C7—H7A	0.9900	C27—H27	0.9500
C7—H7B	0.9900	C28—C29	1.391 (4)
C8—C11	1.530 (4)	C28—C31	1.507 (4)
C8—C10	1.531 (4)	C29—C30	1.386 (4)
C8—C9	1.531 (4)	C29—H29	0.9500
C9—H9A	0.9900	C30—H30	0.9500
C9—H9B	0.9900	C31—H31A	0.9800
C10—H10A	0.9800	C31—H31B	0.9800
C10—H10B	0.9800	C31—H31C	0.9800
C10—H10C	0.9800	C32—H32	0.9500
C11—H11A	0.9800	C33—H33A	0.9800
C11—H11B	0.9800	C33—H33B	0.9800
C11—H11C	0.9800	C33—H33C	0.9800
C12—C13	1.498 (4)	C34—H34A	0.9800
C13—C14	1.372 (4)	C34—H34B	0.9800
C13—C18	1.406 (4)	C34—H34C	0.9800
C14—C15	1.398 (4)

C5—N1—C1	118.0 (2)	C14—C15—H15	120.1
C5—N1—C25	121.3 (2)	C15—C16—C17	121.8 (3)
C1—N1—C25	120.6 (2)	C15—C16—H16	119.1
C32—N2—C34	125.0 (3)	C17—C16—H16	119.1
C32—N2—C33	120.8 (3)	C18—C17—C16	118.4 (2)
C34—N2—C33	113.9 (3)	C18—C17—H17	120.8
C2—C1—N1	121.1 (2)	C16—C17—H17	120.8
C2—C1—C9	123.0 (2)	C17—C18—C13	119.6 (2)
N1—C1—C9	115.8 (2)	C17—C18—C5	134.6 (2)
C1—C2—C6	119.6 (2)	C13—C18—C5	105.8 (2)
C1—C2—C3	123.8 (2)	C20—C19—C24	117.3 (2)
C6—C2—C3	116.6 (2)	C20—C19—C3	123.4 (2)
C4—C3—C2	107.5 (2)	C24—C19—C3	119.2 (2)
C4—C3—C19	109.5 (2)	C21—C20—C19	121.3 (3)
C2—C3—C19	112.5 (2)	C21—C20—Cl1	117.3 (2)
C4—C3—H3	109.1	C19—C20—Cl1	121.4 (2)
C2—C3—H3	109.1	C22—C21—C20	120.3 (3)
C19—C3—H3	109.1	C22—C21—H21	119.9
C5—C4—C12	108.8 (2)	C20—C21—H21	119.9
C5—C4—C3	123.4 (2)	C21—C22—C23	119.7 (3)
C12—C4—C3	127.6 (2)	C21—C22—H22	120.2
C4—C5—N1	122.5 (2)	C23—C22—H22	120.2
C4—C5—C18	110.7 (2)	C24—C23—C22	119.8 (3)
N1—C5—C18	126.8 (2)	C24—C23—H23	120.1
O1—C6—C2	119.9 (2)	C22—C23—H23	120.1
O1—C6—C7	121.4 (2)	C23—C24—C19	121.6 (3)
C2—C6—C7	118.7 (2)	C23—C24—H24	119.2
C6—C7—C8	114.1 (2)	C19—C24—H24	119.2
C6—C7—H7A	108.7	C26—C25—C30	121.0 (2)
C8—C7—H7A	108.7	C26—C25—N1	120.1 (2)
C6—C7—H7B	108.7	C30—C25—N1	118.8 (2)
C8—C7—H7B	108.7	C25—C26—C27	119.4 (2)
H7A—C7—H7B	107.6	C25—C26—H26	120.3
C7—C8—C11	110.8 (2)	C27—C26—H26	120.3
C7—C8—C10	109.6 (2)	C28—C27—C26	121.1 (2)
C11—C8—C10	109.5 (2)	C28—C27—H27	119.5
C7—C8—C9	108.4 (2)	C26—C27—H27	119.5
C11—C8—C9	108.0 (2)	C27—C28—C29	118.3 (2)
C10—C8—C9	110.6 (2)	C27—C28—C31	121.0 (3)
C1—C9—C8	114.4 (2)	C29—C28—C31	120.7 (3)
C1—C9—H9A	108.7	C30—C29—C28	121.6 (2)
C8—C9—H9A	108.7	C30—C29—H29	119.2
C1—C9—H9B	108.7	C28—C29—H29	119.2
C8—C9—H9B	108.7	C25—C30—C29	118.6 (2)
H9A—C9—H9B	107.6	C25—C30—H30	120.7
C8—C10—H10A	109.5	C29—C30—H30	120.7
C8—C10—H10B	109.5	C28—C31—H31A	109.5
H10A—C10—H10B	109.5	C28—C31—H31B	109.5
C8—C10—H10C	109.5	H31A—C31—H31B	109.5
H10A—C10—H10C	109.5	C28—C31—H31C	109.5
H10B—C10—H10C	109.5	H31A—C31—H31C	109.5
C8—C11—H11A	109.5	H31B—C31—H31C	109.5
C8—C11—H11B	109.5	O3—C32—N2	124.0 (4)
H11A—C11—H11B	109.5	O3—C32—H32	118.0
C8—C11—H11C	109.5	N2—C32—H32	118.0
H11A—C11—H11C	109.5	N2—C33—H33A	109.5
H11B—C11—H11C	109.5	N2—C33—H33B	109.5
O2—C12—C4	127.7 (2)	H33A—C33—H33B	109.5
O2—C12—C13	126.2 (2)	N2—C33—H33C	109.5
C4—C12—C13	106.1 (2)	H33A—C33—H33C	109.5
C14—C13—C18	122.0 (2)	H33B—C33—H33C	109.5
C14—C13—C12	129.4 (2)	N2—C34—H34A	109.5
C18—C13—C12	108.6 (2)	N2—C34—H34B	109.5
C13—C14—C15	118.3 (2)	H34A—C34—H34B	109.5
C13—C14—H14	120.8	N2—C34—H34C	109.5
C15—C14—H14	120.8	H34A—C34—H34C	109.5
C16—C15—C14	119.9 (3)	H34B—C34—H34C	109.5
C16—C15—H15	120.1

C5—N1—C1—C2	−9.5 (4)	C18—C13—C14—C15	−0.4 (4)
C25—N1—C1—C2	175.7 (2)	C12—C13—C14—C15	−177.7 (3)
C5—N1—C1—C9	168.8 (2)	C13—C14—C15—C16	−0.9 (4)
C25—N1—C1—C9	−5.9 (3)	C14—C15—C16—C17	1.0 (4)
N1—C1—C2—C6	175.8 (2)	C15—C16—C17—C18	0.2 (4)
C9—C1—C2—C6	−2.4 (4)	C16—C17—C18—C13	−1.5 (4)
N1—C1—C2—C3	−4.6 (4)	C16—C17—C18—C5	176.7 (3)
C9—C1—C2—C3	177.2 (2)	C14—C13—C18—C17	1.6 (4)
C1—C2—C3—C4	17.9 (3)	C12—C13—C18—C17	179.4 (2)
C6—C2—C3—C4	−162.5 (2)	C14—C13—C18—C5	−177.0 (2)
C1—C2—C3—C19	−102.7 (3)	C12—C13—C18—C5	0.7 (3)
C6—C2—C3—C19	76.9 (3)	C4—C5—C18—C17	179.7 (3)
C2—C3—C4—C5	−20.0 (3)	N1—C5—C18—C17	−3.2 (5)
C19—C3—C4—C5	102.5 (3)	C4—C5—C18—C13	−1.9 (3)
C2—C3—C4—C12	164.5 (2)	N1—C5—C18—C13	175.2 (2)
C19—C3—C4—C12	−73.0 (3)	C4—C3—C19—C20	110.3 (3)
C12—C4—C5—N1	−175.0 (2)	C2—C3—C19—C20	−130.2 (3)
C3—C4—C5—N1	8.8 (4)	C4—C3—C19—C24	−66.3 (3)
C12—C4—C5—C18	2.3 (3)	C2—C3—C19—C24	53.2 (3)
C3—C4—C5—C18	−173.9 (2)	C24—C19—C20—C21	2.5 (4)
C1—N1—C5—C4	7.5 (4)	C3—C19—C20—C21	−174.2 (2)
C25—N1—C5—C4	−177.8 (2)	C24—C19—C20—Cl1	−177.5 (2)
C1—N1—C5—C18	−169.3 (2)	C3—C19—C20—Cl1	5.9 (4)
C25—N1—C5—C18	5.4 (4)	C19—C20—C21—C22	−1.0 (4)
C1—C2—C6—O1	−179.3 (2)	Cl1—C20—C21—C22	178.9 (2)
C3—C2—C6—O1	1.0 (4)	C20—C21—C22—C23	−1.3 (4)
C1—C2—C6—C7	−1.4 (4)	C21—C22—C23—C24	1.9 (4)
C3—C2—C6—C7	179.0 (2)	C22—C23—C24—C19	−0.3 (4)
O1—C6—C7—C8	−152.1 (2)	C20—C19—C24—C23	−1.8 (4)
C2—C6—C7—C8	30.0 (3)	C3—C19—C24—C23	175.0 (2)
C6—C7—C8—C11	−169.9 (2)	C5—N1—C25—C26	−88.0 (3)
C6—C7—C8—C10	69.2 (3)	C1—N1—C25—C26	86.5 (3)
C6—C7—C8—C9	−51.6 (3)	C5—N1—C25—C30	92.5 (3)
C2—C1—C9—C8	−22.4 (4)	C1—N1—C25—C30	−92.9 (3)
N1—C1—C9—C8	159.3 (2)	C30—C25—C26—C27	−0.7 (4)
C7—C8—C9—C1	47.8 (3)	N1—C25—C26—C27	179.9 (2)
C11—C8—C9—C1	167.8 (2)	C25—C26—C27—C28	−0.6 (4)
C10—C8—C9—C1	−72.4 (3)	C26—C27—C28—C29	1.2 (4)
C5—C4—C12—O2	176.5 (3)	C26—C27—C28—C31	−179.8 (2)
C3—C4—C12—O2	−7.4 (4)	C27—C28—C29—C30	−0.6 (4)
C5—C4—C12—C13	−1.8 (3)	C31—C28—C29—C30	−179.6 (2)
C3—C4—C12—C13	174.3 (2)	C26—C25—C30—C29	1.3 (4)
O2—C12—C13—C14	−0.2 (4)	N1—C25—C30—C29	−179.3 (2)
C4—C12—C13—C14	178.1 (3)	C28—C29—C30—C25	−0.7 (4)
O2—C12—C13—C18	−177.8 (3)	C34—N2—C32—O3	−178.0 (3)
C4—C12—C13—C18	0.6 (3)	C33—N2—C32—O3	−5.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C34—H34A···O1ⁱ	0.98	2.51	3.259 (4)	133
C30—H30···O3ⁱⁱ	0.95	2.55	3.444 (4)	157
C15—H15···O3ⁱⁱⁱ	0.95	2.44	3.371 (4)	167

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

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