1-(4-Chloro­benz­yl)-6,6-dimethyl-2-phenyl-1,5,6,7-tetra­hydro-4H-indol-4-one

In the title compound, C₂₃H₂₂ClNO, there are two independent mol­ecules showing similar conformations, the tetra­hydro­indole ring system being approximately planar except for the dimethyl-substituted C atom. Mol­ecules are linked via C—H...O, C—H...π and C—H...Cl inter­actions, forming a sheet-like structure.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.088
• wR factor = 0.200
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C36
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  CL2     ..       2.86 Ang.

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

1-(4-Chlorobenzyl)-6,6-dimethyl-2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one

Crystal data

C23H22ClNO	Z = 4
Mr = 363.87	F(000) = 768
Triclinic, P1	Dx = 1.251 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7761 (14) Å	Cell parameters from 636 reflections
b = 13.0082 (19) Å	θ = 1.4–26.4°
c = 15.832 (2) Å	µ = 0.21 mm^−1
α = 75.900 (3)°	T = 290 K
β = 87.872 (3)°	Plates, colorless
γ = 81.639 (3)°	0.21 × 0.06 × 0.02 mm
V = 1931.9 (5) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	7488 independent reflections
Radiation source: fine-focus sealed tube	3904 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.946, Tmax = 0.996	k = −16→15
15035 measured reflections	l = −19→19

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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0861P)^2] where P = (Fo^2 + 2Fc^2)/3
7488 reflections	(Δ/σ)max < 0.001
473 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.27 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	1.20395 (14)	0.43988 (10)	0.07239 (10)	0.0978 (5)
Cl2	0.27981 (17)	0.66894 (12)	0.86128 (12)	0.1207 (6)
N1	0.7614 (3)	0.8794 (2)	0.10571 (18)	0.0419 (7)
N2	0.7329 (3)	0.4188 (2)	0.62132 (17)	0.0420 (8)
O1	0.6821 (4)	1.1688 (2)	−0.12549 (19)	0.0963 (12)
O2	0.8360 (3)	0.6398 (2)	0.36300 (18)	0.0705 (9)
C1	0.8024 (4)	0.9679 (3)	0.1282 (2)	0.0469 (10)
C2	0.7758 (4)	1.0526 (3)	0.0592 (2)	0.0552 (11)
C3	0.6753 (5)	1.0740 (3)	−0.0948 (3)	0.0620 (12)
C4	0.6154 (5)	1.0083 (3)	−0.1470 (3)	0.0652 (12)
C5	0.6720 (4)	0.8888 (3)	−0.1249 (2)	0.0546 (11)
C6	0.6574 (4)	0.8414 (3)	−0.0268 (2)	0.0492 (10)
C7	0.7111 (4)	0.9106 (3)	0.0231 (2)	0.0447 (9)
C8	0.7180 (4)	1.0184 (3)	−0.0080 (2)	0.0503 (10)
C9	0.7665 (4)	0.7720 (3)	0.1616 (2)	0.0471 (10)
C10	0.8776 (4)	0.6906 (3)	0.1376 (2)	0.0413 (9)
C11	0.8711 (5)	0.5833 (3)	0.1716 (2)	0.0566 (11)
C12	0.9717 (5)	0.5067 (3)	0.1513 (3)	0.0648 (13)
C13	1.0789 (5)	0.5374 (3)	0.0980 (3)	0.0603 (12)
C14	1.0890 (5)	0.6430 (3)	0.0653 (3)	0.0639 (12)
C15	0.9877 (4)	0.7196 (3)	0.0847 (3)	0.0555 (11)
C16	0.8666 (4)	0.9620 (3)	0.2125 (2)	0.0473 (10)
C17	0.8136 (5)	1.0342 (3)	0.2611 (3)	0.0647 (12)
C18	0.8784 (5)	1.0357 (4)	0.3372 (3)	0.0756 (14)
C19	0.9947 (5)	0.9661 (4)	0.3660 (3)	0.0724 (14)
C20	1.0476 (5)	0.8944 (4)	0.3188 (3)	0.0749 (14)
C21	0.9842 (5)	0.8915 (3)	0.2434 (3)	0.0645 (12)
C22	0.5888 (5)	0.8311 (4)	−0.1751 (3)	0.0811 (15)
C23	0.8242 (5)	0.8717 (3)	−0.1513 (3)	0.0716 (13)
C24	0.6837 (4)	0.3824 (3)	0.5535 (2)	0.0431 (9)
C25	0.7171 (4)	0.4492 (3)	0.4779 (2)	0.0483 (10)
C26	0.8428 (4)	0.6182 (3)	0.4426 (3)	0.0503 (10)
C27	0.9162 (4)	0.6825 (3)	0.4888 (2)	0.0564 (11)
C28	0.8679 (4)	0.6836 (3)	0.5821 (2)	0.0520 (10)
C29	0.8646 (4)	0.5681 (3)	0.6364 (2)	0.0468 (10)
C30	0.7953 (4)	0.5070 (3)	0.5864 (2)	0.0420 (9)
C31	0.7859 (4)	0.5281 (3)	0.4980 (2)	0.0427 (9)
C32	0.7097 (4)	0.3798 (3)	0.7138 (2)	0.0461 (10)
C33	0.5937 (4)	0.4487 (3)	0.7494 (2)	0.0438 (9)
C34	0.5587 (5)	0.4211 (3)	0.8365 (3)	0.0601 (11)
C35	0.4616 (5)	0.4878 (4)	0.8718 (3)	0.0740 (14)
C36	0.3998 (5)	0.5823 (4)	0.8183 (4)	0.0698 (13)
C37	0.4289 (5)	0.6093 (4)	0.7319 (3)	0.0672 (12)
C38	0.5255 (4)	0.5420 (3)	0.6977 (3)	0.0566 (11)
C39	0.6191 (4)	0.2838 (3)	0.5678 (2)	0.0449 (10)
C40	0.6722 (4)	0.2059 (3)	0.5247 (3)	0.0571 (11)
C41	0.6184 (5)	0.1121 (4)	0.5367 (3)	0.0671 (13)
C42	0.5105 (5)	0.0919 (3)	0.5931 (3)	0.0665 (13)
C43	0.4539 (5)	0.1690 (4)	0.6351 (3)	0.0658 (12)
C44	0.5073 (4)	0.2636 (3)	0.6225 (3)	0.0571 (11)
C45	0.9699 (5)	0.7351 (4)	0.6246 (3)	0.0783 (14)
C46	0.7236 (5)	0.7492 (3)	0.5801 (3)	0.0705 (13)
H2	0.7926	1.1219	0.0564	0.066*
H4A	0.6324	1.0379	−0.2082	0.078*
H4B	0.5160	1.0159	−0.1383	0.078*
H6A	0.5609	0.8364	−0.0124	0.059*
H6B	0.7088	0.7699	−0.0111	0.059*
H9A	0.6775	0.7481	0.1595	0.057*
H9B	0.7813	0.7750	0.2212	0.057*
H11	0.7986	0.5623	0.2083	0.068*
H12	0.9663	0.4344	0.1739	0.078*
H14	1.1636	0.6634	0.0302	0.077*
H15	0.9938	0.7918	0.0618	0.067*
H17	0.7340	1.0819	0.2425	0.078*
H18	0.8421	1.0848	0.3690	0.091*
H19	1.0376	0.9673	0.4171	0.087*
H20	1.1273	0.8469	0.3378	0.090*
H21	1.0210	0.8414	0.2126	0.077*
H22A	0.4953	0.8342	−0.1541	0.122*
H22B	0.6300	0.7577	−0.1664	0.122*
H22C	0.5893	0.8655	−0.2360	0.122*
H23A	0.8331	0.9010	−0.2128	0.107*
H23B	0.8579	0.7964	−0.1378	0.107*
H23C	0.8772	0.9068	−0.1200	0.107*
H25	0.6978	0.4439	0.4222	0.058*
H27A	0.9058	0.7559	0.4543	0.068*
H27B	1.0140	0.6551	0.4905	0.068*
H29A	0.9582	0.5330	0.6506	0.056*
H29B	0.8151	0.5695	0.6904	0.056*
H32A	0.7944	0.3772	0.7449	0.055*
H32B	0.6877	0.3073	0.7247	0.055*
H34	0.6006	0.3571	0.8718	0.072*
H35	0.4385	0.4692	0.9306	0.089*
H37	0.3844	0.6721	0.6963	0.081*
H38	0.5453	0.5599	0.6385	0.068*
H40	0.7461	0.2177	0.4866	0.068*
H41	0.6554	0.0616	0.5064	0.080*
H42	0.4761	0.0270	0.6029	0.080*
H43	0.3790	0.1569	0.6723	0.079*
H44	0.4675	0.3151	0.6512	0.069*
H45A	1.0601	0.6940	0.6267	0.117*
H45B	0.9395	0.7368	0.6827	0.117*
H45C	0.9738	0.8069	0.5910	0.117*
H46A	0.7275	0.8216	0.5481	0.106*
H46B	0.6933	0.7487	0.6386	0.106*
H46C	0.6598	0.7183	0.5524	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.075 (3)	0.038 (2)	0.054 (2)	−0.011 (2)	−0.007 (2)	−0.004 (2)
C12	0.095 (4)	0.032 (2)	0.066 (3)	−0.006 (3)	−0.020 (3)	−0.006 (2)
N1	0.052 (2)	0.0342 (18)	0.0377 (17)	−0.0029 (15)	0.0026 (15)	−0.0071 (14)
N2	0.051 (2)	0.0402 (18)	0.0340 (17)	−0.0035 (16)	−0.0041 (14)	−0.0094 (14)
O1	0.165 (4)	0.0394 (19)	0.070 (2)	−0.001 (2)	−0.010 (2)	0.0075 (16)
O2	0.093 (2)	0.071 (2)	0.0431 (17)	−0.0137 (17)	0.0111 (15)	−0.0059 (14)
C1	0.052 (3)	0.035 (2)	0.054 (2)	−0.0035 (19)	0.003 (2)	−0.0134 (19)
C2	0.074 (3)	0.029 (2)	0.059 (3)	−0.004 (2)	0.004 (2)	−0.007 (2)
C3	0.082 (3)	0.038 (3)	0.057 (3)	0.009 (2)	0.009 (2)	−0.005 (2)
C4	0.079 (3)	0.056 (3)	0.051 (3)	0.013 (2)	−0.010 (2)	−0.005 (2)
C5	0.060 (3)	0.054 (3)	0.046 (2)	0.004 (2)	0.000 (2)	−0.013 (2)
C6	0.051 (2)	0.044 (2)	0.051 (2)	−0.0027 (19)	−0.0019 (19)	−0.0106 (18)
C7	0.047 (2)	0.037 (2)	0.047 (2)	0.0003 (18)	0.0062 (19)	−0.0099 (18)
C8	0.066 (3)	0.035 (2)	0.046 (2)	0.001 (2)	0.000 (2)	−0.0075 (18)
C9	0.060 (3)	0.038 (2)	0.043 (2)	−0.014 (2)	0.0057 (19)	−0.0049 (18)
C10	0.056 (3)	0.033 (2)	0.034 (2)	−0.0069 (19)	−0.0057 (19)	−0.0041 (16)
Cl1	0.0971 (10)	0.0620 (8)	0.1355 (12)	0.0245 (7)	−0.0159 (9)	−0.0447 (8)
Cl2	0.1243 (13)	0.0881 (11)	0.1679 (15)	−0.0251 (9)	0.0709 (11)	−0.0705 (11)
C13	0.068 (3)	0.046 (3)	0.069 (3)	0.005 (2)	−0.017 (3)	−0.022 (2)
C14	0.065 (3)	0.054 (3)	0.068 (3)	0.000 (2)	0.008 (2)	−0.014 (2)
C15	0.071 (3)	0.032 (2)	0.058 (3)	−0.005 (2)	0.006 (2)	−0.0040 (19)
C16	0.052 (3)	0.036 (2)	0.056 (2)	−0.013 (2)	0.007 (2)	−0.0117 (19)
C17	0.064 (3)	0.062 (3)	0.076 (3)	−0.009 (2)	−0.001 (2)	−0.031 (2)
C18	0.091 (4)	0.074 (3)	0.078 (3)	−0.028 (3)	0.005 (3)	−0.042 (3)
C19	0.088 (4)	0.073 (3)	0.061 (3)	−0.027 (3)	−0.013 (3)	−0.013 (3)
C20	0.091 (4)	0.062 (3)	0.069 (3)	−0.005 (3)	−0.019 (3)	−0.011 (3)
C21	0.078 (3)	0.051 (3)	0.065 (3)	−0.003 (2)	−0.005 (3)	−0.017 (2)
C22	0.101 (4)	0.074 (3)	0.069 (3)	0.004 (3)	−0.026 (3)	−0.023 (3)
C23	0.081 (4)	0.065 (3)	0.065 (3)	−0.001 (3)	0.021 (3)	−0.017 (2)
C24	0.046 (2)	0.046 (2)	0.038 (2)	−0.0035 (19)	−0.0037 (18)	−0.0137 (18)
C25	0.055 (3)	0.057 (3)	0.035 (2)	−0.001 (2)	−0.0077 (19)	−0.0195 (19)
C26	0.055 (3)	0.050 (3)	0.042 (2)	0.002 (2)	0.005 (2)	−0.011 (2)
C27	0.065 (3)	0.046 (2)	0.057 (3)	−0.009 (2)	0.002 (2)	−0.009 (2)
C28	0.063 (3)	0.040 (2)	0.056 (2)	−0.010 (2)	−0.001 (2)	−0.0158 (19)
C29	0.052 (2)	0.048 (2)	0.044 (2)	−0.0068 (19)	−0.0018 (19)	−0.0172 (18)
C30	0.050 (2)	0.034 (2)	0.042 (2)	−0.0040 (19)	0.0003 (18)	−0.0105 (17)
C31	0.049 (2)	0.041 (2)	0.037 (2)	−0.0012 (19)	−0.0024 (18)	−0.0110 (17)
C32	0.054 (3)	0.043 (2)	0.040 (2)	−0.0062 (19)	−0.0055 (19)	−0.0066 (17)
C33	0.050 (2)	0.049 (2)	0.038 (2)	−0.017 (2)	−0.0008 (19)	−0.0152 (19)
C34	0.077 (3)	0.055 (3)	0.050 (3)	−0.014 (2)	0.005 (2)	−0.014 (2)
C35	0.098 (4)	0.077 (4)	0.056 (3)	−0.030 (3)	0.027 (3)	−0.028 (3)
C36	0.069 (3)	0.060 (3)	0.096 (4)	−0.024 (3)	0.028 (3)	−0.044 (3)
C37	0.059 (3)	0.055 (3)	0.087 (4)	−0.006 (2)	0.010 (3)	−0.018 (3)
C38	0.054 (3)	0.061 (3)	0.051 (2)	−0.002 (2)	0.001 (2)	−0.010 (2)
C44	0.059 (3)	0.060 (3)	0.057 (3)	−0.008 (2)	0.000 (2)	−0.023 (2)
C39	0.042 (2)	0.050 (2)	0.044 (2)	−0.004 (2)	−0.0084 (19)	−0.0147 (19)
C40	0.056 (3)	0.063 (3)	0.062 (3)	−0.012 (2)	−0.002 (2)	−0.031 (2)
C41	0.071 (3)	0.059 (3)	0.083 (3)	−0.009 (3)	−0.004 (3)	−0.039 (3)
C42	0.081 (4)	0.051 (3)	0.073 (3)	−0.021 (3)	−0.016 (3)	−0.014 (2)
C43	0.070 (3)	0.072 (3)	0.062 (3)	−0.030 (3)	0.005 (2)	−0.016 (2)
C45	0.096 (4)	0.070 (3)	0.081 (3)	−0.036 (3)	0.000 (3)	−0.027 (3)
C46	0.086 (4)	0.049 (3)	0.074 (3)	0.005 (3)	0.003 (3)	−0.019 (2)

Geometric parameters (Å, º)

C40—C41	1.366 (5)	C5—C4	1.532 (5)
C40—C39	1.386 (5)	C5—C22	1.540 (5)
C40—H40	0.9300	C2—H2	0.9300
C33—C34	1.380 (5)	C3—C4	1.510 (6)
C33—C38	1.382 (5)	C38—C37	1.380 (5)
C33—C32	1.520 (5)	C38—H38	0.9300
C9—C10	1.510 (5)	C25—H25	0.9300
C9—H9A	0.9700	C28—C46	1.536 (5)
C9—H9B	0.9700	C28—C45	1.537 (5)
Cl1—C13	1.741 (4)	C44—C43	1.374 (5)
Cl2—C36	1.743 (4)	C44—H44	0.9300
N1—C1	1.398 (4)	C14—C13	1.361 (6)
N1—C7	1.360 (4)	C14—H14	0.9300
N1—C9	1.455 (4)	C17—C18	1.389 (6)
N2—C24	1.400 (4)	C17—H17	0.9300
N2—C30	1.365 (4)	C11—C12	1.382 (6)
N2—C32	1.450 (4)	C11—H11	0.9300
O1—C3	1.221 (4)	C34—C35	1.387 (6)
O2—C26	1.224 (4)	C34—H34	0.9300
C10—C15	1.377 (5)	C41—C42	1.370 (6)
C10—C11	1.378 (5)	C41—H41	0.9300
C30—C31	1.362 (5)	C12—C13	1.364 (6)
C30—C29	1.490 (5)	C12—H12	0.9300
C31—C25	1.408 (5)	C37—C36	1.357 (6)
C31—C26	1.452 (5)	C37—H37	0.9300
C7—C8	1.379 (5)	C36—C35	1.381 (6)
C7—C6	1.492 (5)	C4—H4A	0.9700
C39—C44	1.385 (5)	C4—H4B	0.9700
C39—C24	1.476 (5)	C18—C19	1.364 (6)
C6—C5	1.534 (5)	C18—H18	0.9300
C6—H6A	0.9700	C42—C43	1.375 (6)
C6—H6B	0.9700	C42—H42	0.9300
C8—C2	1.414 (5)	C43—H43	0.9300
C8—C3	1.434 (5)	C21—C20	1.376 (6)
C24—C25	1.358 (5)	C21—H21	0.9300
C29—C28	1.542 (5)	C35—H35	0.9300
C29—H29A	0.9700	C22—H22A	0.9600
C29—H29B	0.9700	C22—H22B	0.9600
C32—H32A	0.9700	C22—H22C	0.9600
C32—H32B	0.9700	C46—H46A	0.9600
C16—C21	1.385 (5)	C46—H46B	0.9600
C16—C17	1.386 (5)	C46—H46C	0.9600
C16—C1	1.477 (5)	C45—H45A	0.9600
C1—C2	1.352 (5)	C45—H45B	0.9600
C27—C26	1.504 (5)	C45—H45C	0.9600
C27—C28	1.537 (5)	C20—C19	1.366 (6)
C27—H27A	0.9700	C20—H20	0.9300
C27—H27B	0.9700	C23—H23A	0.9600
C15—C14	1.382 (5)	C23—H23B	0.9600
C15—H15	0.9300	C23—H23C	0.9600
C5—C23	1.531 (6)	C19—H19	0.9300
C41—C40—C39	121.6 (4)	C24—C25—C31	108.5 (3)
C41—C40—H40	119.2	C24—C25—H25	125.8
C39—C40—H40	119.2	C31—C25—H25	125.8
C34—C33—C38	118.3 (4)	C46—C28—C27	109.8 (3)
C34—C33—C32	119.9 (4)	C46—C28—C45	109.1 (3)
C38—C33—C32	121.7 (3)	C27—C28—C45	109.2 (3)
N1—C9—C10	114.3 (3)	C46—C28—C29	110.1 (3)
N1—C9—H9A	108.7	C27—C28—C29	110.0 (3)
C10—C9—H9A	108.7	C45—C28—C29	108.7 (3)
N1—C9—H9B	108.7	C43—C44—C39	121.2 (4)
C10—C9—H9B	108.7	C43—C44—H44	119.4
H9A—C9—H9B	107.6	C39—C44—H44	119.4
C30—N2—C24	108.8 (3)	C13—C14—C15	119.5 (4)
C30—N2—C32	123.7 (3)	C13—C14—H14	120.3
C24—N2—C32	127.1 (3)	C15—C14—H14	120.3
C7—N1—C1	108.8 (3)	C16—C17—C18	120.5 (4)
C7—N1—C9	124.9 (3)	C16—C17—H17	119.8
C1—N1—C9	126.3 (3)	C18—C17—H17	119.8
C15—C10—C11	118.6 (4)	C10—C11—C12	120.4 (4)
C15—C10—C9	122.4 (3)	C10—C11—H11	119.8
C11—C10—C9	119.0 (4)	C12—C11—H11	119.8
C31—C30—N2	108.3 (3)	C33—C34—C35	120.7 (4)
C31—C30—C29	125.9 (3)	C33—C34—H34	119.6
N2—C30—C29	125.8 (3)	C35—C34—H34	119.6
C30—C31—C25	107.6 (3)	C40—C41—C42	120.5 (4)
C30—C31—C26	121.1 (3)	C40—C41—H41	119.8
C25—C31—C26	131.4 (3)	C42—C41—H41	119.8
N1—C7—C8	108.5 (3)	C13—C12—C11	119.9 (4)
N1—C7—C6	126.6 (3)	C13—C12—H12	120.1
C8—C7—C6	124.9 (3)	C11—C12—H12	120.1
C44—C39—C40	117.2 (4)	C36—C37—C38	118.9 (4)
C44—C39—C24	123.8 (3)	C36—C37—H37	120.6
C40—C39—C24	119.0 (4)	C38—C37—H37	120.6
C7—C6—C5	110.0 (3)	C37—C36—C35	121.5 (4)
C7—C6—H6A	109.7	C37—C36—Cl2	118.6 (4)
C5—C6—H6A	109.7	C35—C36—Cl2	119.9 (4)
C7—C6—H6B	109.7	C3—C4—C5	115.5 (3)
C5—C6—H6B	109.7	C3—C4—H4A	108.4
H6A—C6—H6B	108.2	C5—C4—H4A	108.4
C7—C8—C2	106.7 (3)	C3—C4—H4B	108.4
C7—C8—C3	121.5 (4)	C5—C4—H4B	108.4
C2—C8—C3	131.8 (4)	H4A—C4—H4B	107.5
C25—C24—N2	106.9 (3)	C14—C13—C12	120.7 (4)
C25—C24—C39	129.7 (3)	C14—C13—Cl1	120.0 (4)
N2—C24—C39	123.2 (3)	C12—C13—Cl1	119.3 (4)
C30—C29—C28	110.1 (3)	C19—C18—C17	120.8 (4)
C30—C29—H29A	109.6	C19—C18—H18	119.6
C28—C29—H29A	109.6	C17—C18—H18	119.6
C30—C29—H29B	109.6	C41—C42—C43	119.0 (4)
C28—C29—H29B	109.6	C41—C42—H42	120.5
H29A—C29—H29B	108.1	C43—C42—H42	120.5
N2—C32—C33	113.1 (3)	C44—C43—C42	120.5 (4)
N2—C32—H32A	109.0	C44—C43—H43	119.8
C33—C32—H32A	109.0	C42—C43—H43	119.8
N2—C32—H32B	109.0	C20—C21—C16	121.1 (4)
C33—C32—H32B	109.0	C20—C21—H21	119.4
H32A—C32—H32B	107.8	C16—C21—H21	119.4
C21—C16—C17	117.7 (4)	C36—C35—C34	118.9 (4)
C21—C16—C1	122.8 (3)	C36—C35—H35	120.6
C17—C16—C1	119.4 (4)	C34—C35—H35	120.6
C2—C1—N1	107.4 (3)	C5—C22—H22A	109.5
C2—C1—C16	129.2 (3)	C5—C22—H22B	109.5
N1—C1—C16	123.3 (3)	H22A—C22—H22B	109.5
C26—C27—C28	116.4 (3)	C5—C22—H22C	109.5
C26—C27—H27A	108.2	H22A—C22—H22C	109.5
C28—C27—H27A	108.2	H22B—C22—H22C	109.5
C26—C27—H27B	108.2	C28—C46—H46A	109.5
C28—C27—H27B	108.2	C28—C46—H46B	109.5
H27A—C27—H27B	107.3	H46A—C46—H46B	109.5
O2—C26—C31	122.9 (4)	C28—C46—H46C	109.5
O2—C26—C27	121.3 (4)	H46A—C46—H46C	109.5
C31—C26—C27	115.8 (3)	H46B—C46—H46C	109.5
C10—C15—C14	120.9 (4)	C28—C45—H45A	109.5
C10—C15—H15	119.5	C28—C45—H45B	109.5
C14—C15—H15	119.5	H45A—C45—H45B	109.5
C23—C5—C4	110.4 (4)	C28—C45—H45C	109.5
C23—C5—C6	109.6 (3)	H45A—C45—H45C	109.5
C4—C5—C6	109.7 (3)	H45B—C45—H45C	109.5
C23—C5—C22	108.8 (3)	C19—C20—C21	120.7 (5)
C4—C5—C22	109.1 (3)	C19—C20—H20	119.7
C6—C5—C22	109.1 (3)	C21—C20—H20	119.7
C1—C2—C8	108.7 (3)	C5—C23—H23A	109.5
C1—C2—H2	125.7	C5—C23—H23B	109.5
C8—C2—H2	125.7	H23A—C23—H23B	109.5
O1—C3—C8	123.7 (4)	C5—C23—H23C	109.5
O1—C3—C4	120.8 (4)	H23A—C23—H23C	109.5
C8—C3—C4	115.5 (4)	H23B—C23—H23C	109.5
C37—C38—C33	121.6 (4)	C18—C19—C20	119.2 (4)
C37—C38—H38	119.2	C18—C19—H19	120.4
C33—C38—H38	119.2	C20—C19—H19	120.4
C10—C9—N1—C7	74.5 (4)	C11—C12—C13—C14	0.8 (6)
C10—C9—N1—C1	−107.8 (4)	C11—C12—C13—Cl1	−179.5 (3)
N1—C9—C10—C15	17.3 (5)	C16—C17—C18—C19	−0.4 (7)
N1—C9—C10—C11	−164.4 (3)	C40—C41—C42—C43	2.3 (6)
C1—N1—C7—C8	−0.5 (4)	C39—C44—C43—C42	−0.3 (6)
C9—N1—C7—C8	177.6 (3)	C41—C42—C43—C44	−1.8 (6)
C1—N1—C7—C6	179.4 (3)	C17—C16—C21—C20	−1.1 (6)
C9—N1—C7—C6	−2.6 (6)	C1—C16—C21—C20	174.6 (4)
C41—C40—C39—C44	−1.3 (6)	C37—C36—C35—C34	2.1 (7)
C41—C40—C39—C24	178.7 (3)	Cl2—C36—C35—C34	−178.8 (3)
N1—C7—C6—C5	−154.6 (3)	C33—C34—C35—C36	0.3 (6)
C8—C7—C6—C5	25.2 (5)	C16—C21—C20—C19	0.9 (7)
N1—C7—C8—C2	0.3 (4)	C17—C18—C19—C20	0.2 (7)
C6—C7—C8—C2	−179.6 (3)	C21—C20—C19—C18	−0.4 (7)
N1—C7—C8—C3	178.4 (4)	C24—N2—C30—C31	0.5 (4)
C6—C7—C8—C3	−1.5 (6)	C32—N2—C30—C31	−173.0 (3)
C7—N1—C1—C2	0.4 (4)	C24—N2—C30—C29	−178.2 (3)
C9—N1—C1—C2	−177.6 (3)	C32—N2—C30—C29	8.3 (5)
C7—N1—C1—C16	−177.8 (3)	N2—C30—C31—C25	−0.8 (4)
C9—N1—C1—C16	4.2 (5)	C29—C30—C31—C25	177.8 (3)
C11—C10—C15—C14	0.6 (5)	N2—C30—C31—C26	179.7 (3)
C9—C10—C15—C14	178.8 (3)	C29—C30—C31—C26	−1.7 (6)
C7—C6—C5—C23	73.0 (4)	C30—N2—C24—C25	0.1 (4)
C7—C6—C5—C4	−48.4 (4)	C32—N2—C24—C25	173.3 (3)
C7—C6—C5—C22	−168.0 (3)	C30—N2—C24—C39	175.6 (3)
N1—C1—C2—C8	−0.3 (4)	C32—N2—C24—C39	−11.1 (5)
C16—C1—C2—C8	177.9 (4)	C44—C39—C24—C25	−130.8 (4)
C7—C8—C2—C1	0.0 (5)	C40—C39—C24—C25	49.3 (6)
C3—C8—C2—C1	−177.8 (4)	C44—C39—C24—N2	54.7 (5)
C7—C8—C3—O1	−178.6 (4)	C40—C39—C24—N2	−125.2 (4)
C2—C8—C3—O1	−1.1 (8)	C31—C30—C29—C28	25.1 (5)
C7—C8—C3—C4	3.4 (6)	N2—C30—C29—C28	−156.5 (3)
C2—C8—C3—C4	−179.1 (4)	C30—N2—C32—C33	73.9 (4)
C10—C15—C14—C13	0.8 (6)	C24—N2—C32—C33	−98.4 (4)
C21—C16—C17—C18	0.9 (6)	C34—C33—C32—N2	179.5 (3)
C1—C16—C17—C18	−175.0 (4)	C38—C33—C32—N2	−3.6 (5)
C15—C10—C11—C12	−1.3 (5)	C30—C31—C26—O2	−179.8 (4)
C9—C10—C11—C12	−179.6 (3)	C25—C31—C26—O2	0.8 (6)
C38—C33—C34—C35	−2.7 (6)	C30—C31—C26—C27	2.3 (5)
C32—C33—C34—C35	174.3 (4)	C25—C31—C26—C27	−177.0 (4)
C39—C40—C41—C42	−0.7 (6)	C28—C27—C26—O2	154.1 (4)
C10—C11—C12—C13	0.7 (6)	C28—C27—C26—C31	−27.9 (5)
C33—C38—C37—C36	−0.5 (6)	C34—C33—C38—C37	2.8 (6)
C38—C37—C36—C35	−2.0 (7)	C32—C33—C38—C37	−174.2 (3)
C38—C37—C36—Cl2	178.9 (3)	N2—C24—C25—C31	−0.6 (4)
O1—C3—C4—C5	151.6 (4)	C39—C24—C25—C31	−175.7 (4)
C8—C3—C4—C5	−30.4 (6)	C30—C31—C25—C24	0.9 (4)
C23—C5—C4—C3	−67.3 (5)	C26—C31—C25—C24	−179.7 (4)
C6—C5—C4—C3	53.6 (5)	C26—C27—C28—C46	−70.6 (4)
C22—C5—C4—C3	173.2 (4)	C26—C27—C28—C45	169.9 (3)
C21—C16—C1—C2	−122.8 (5)	C26—C27—C28—C29	50.7 (5)
C17—C16—C1—C2	52.9 (6)	C30—C29—C28—C46	74.6 (4)
C21—C16—C1—N1	55.1 (5)	C30—C29—C28—C27	−46.6 (4)
C17—C16—C1—N1	−129.2 (4)	C30—C29—C28—C45	−166.0 (3)
C15—C14—C13—C12	−1.5 (6)	C40—C39—C44—C43	1.8 (6)
C15—C14—C13—Cl1	178.7 (3)	C24—C39—C44—C43	−178.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2	0.97	2.51	3.276 (4)	136
C34—H34···O1^i	0.93	2.45	3.245 (5)	143
C4—H4B···Cg1^ii	0.97	2.86	3.804 (5)	163
C27—H27B···Cg2^iii	0.97	2.73	3.653 (4)	159
C38—H38···Cg2	0.93	2.75	3.409 (5)	128
C14—H14···Cl2^iv	0.93	2.86	3.637 (5)	143

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