1-(2-Chloro-acet-yl)-3-methyl-2,6-diphenyl-piperidin-4-one.

The asymmetric unit of the title compound, C(20)H(20)ClNO(2), contains two crystallographically independent mol-ecules of similar geometry. The piperidine ring adopts a distorted boat conformation in both mol-ecules, in which the N atom assumes an almost planar configuration.

Related literature

For the crystal structure of 3,5-dimethyl-bis­(2-methoxy­phen­yl)piperidin-4-one, see: Parthiban et al. (2008 ▶).

Experimental

Crystal data

C20H20ClNO2

M = 341.82

Monoclinic,

a = 31.026 (6) Å

b = 12.417 (2) Å

c = 9.3209 (17) Å

β = 101.423 (4)°

V = 3519.8 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 290 K

0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.956

14797 measured reflections

7013 independent reflections

4933 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.094

S = 1.05

7013 reflections

435 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 3002 Friedel pairs

Flack parameter: 0.04 (5)

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045358/ci2956sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045358/ci2956Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H20ClNO2	F(000) = 1440
Mr = 341.82	Dx = 1.290 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1325 reflections
a = 31.026 (6) Å	θ = 3.0–20.7°
b = 12.417 (2) Å	µ = 0.23 mm−1
c = 9.3209 (17) Å	T = 290 K
β = 101.423 (4)°	Block, colourless
V = 3519.8 (11) Å3	0.25 × 0.23 × 0.20 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	7013 independent reflections
Radiation source: fine-focus sealed tube	4933 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→40
Tmin = 0.945, Tmax = 0.956	k = −16→16
14797 measured reflections	l = −11→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0334P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
7013 reflections	Δρmax = 0.31 e Å−3
435 parameters	Δρmin = −0.13 e Å−3
2 restraints	Absolute structure: Flack (1983), 3002 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (5)

	x	y	z	Uiso*/Ueq
Cl1	0.50000 (3)	0.64105 (6)	0.50836 (9)	0.0634 (2)
Cl2	0.41803 (3)	0.49823 (7)	0.15694 (9)	0.0608 (2)
O1	0.63439 (8)	0.1780 (2)	0.3091 (3)	0.0758 (7)
O2	0.57673 (8)	0.53213 (18)	0.6705 (3)	0.0685 (7)
O3	0.22780 (8)	0.6049 (2)	0.4959 (3)	0.0728 (7)
O4	0.32828 (7)	0.55176 (18)	0.0346 (2)	0.0622 (6)
N1	0.57108 (8)	0.3715 (2)	0.5510 (2)	0.0430 (6)
N2	0.30973 (8)	0.64746 (17)	0.2214 (2)	0.0405 (6)
C1	0.61735 (10)	0.2246 (3)	0.3972 (3)	0.0510 (8)
C2	0.63947 (11)	0.3156 (3)	0.4873 (4)	0.0598 (9)
H2A	0.6395	0.3782	0.4251	0.072*
H2B	0.6698	0.2961	0.5258	0.072*
C3	0.61746 (10)	0.3449 (3)	0.6139 (3)	0.0501 (8)
H3	0.6313	0.4118	0.6560	0.060*
C4	0.54533 (10)	0.2968 (2)	0.4414 (3)	0.0422 (7)
H4	0.5391	0.3344	0.3471	0.051*
C5	0.57193 (10)	0.1944 (2)	0.4222 (3)	0.0470 (8)
H5	0.5761	0.1545	0.5146	0.056*
C6	0.62226 (10)	0.2644 (3)	0.7379 (3)	0.0472 (8)
C7	0.64743 (11)	0.1717 (3)	0.7463 (4)	0.0602 (9)
H7	0.6631	0.1574	0.6730	0.072*
C8	0.64984 (12)	0.1004 (3)	0.8605 (4)	0.0675 (10)
H8	0.6670	0.0388	0.8640	0.081*
C9	0.62698 (13)	0.1204 (3)	0.9686 (4)	0.0695 (10)
H9	0.6279	0.0713	1.0446	0.083*
C10	0.60264 (12)	0.2128 (3)	0.9652 (4)	0.0698 (11)
H10	0.5875	0.2274	1.0397	0.084*
C11	0.60076 (11)	0.2835 (3)	0.8510 (3)	0.0598 (9)
H11	0.5844	0.3464	0.8501	0.072*
C12	0.50134 (10)	0.2664 (2)	0.4800 (3)	0.0443 (7)
C13	0.49875 (13)	0.2290 (3)	0.6171 (4)	0.0621 (10)
H13	0.5242	0.2204	0.6880	0.074*
C14	0.45792 (15)	0.2039 (3)	0.6495 (4)	0.0744 (12)
H14	0.4562	0.1790	0.7423	0.089*
C15	0.42043 (14)	0.2160 (3)	0.5452 (5)	0.0713 (11)
H15	0.3932	0.1996	0.5672	0.086*
C16	0.42293 (12)	0.2519 (3)	0.4098 (5)	0.0649 (9)
H16	0.3974	0.2601	0.3392	0.078*
C17	0.46276 (10)	0.2760 (2)	0.3765 (4)	0.0524 (8)
H17	0.4640	0.2993	0.2826	0.063*
C18	0.55669 (10)	0.4715 (2)	0.5775 (4)	0.0480 (8)
C19	0.51356 (11)	0.5052 (2)	0.4795 (4)	0.0570 (9)
H19A	0.4902	0.4589	0.4985	0.068*
H19B	0.5158	0.4958	0.3780	0.068*
C20	0.54732 (12)	0.1207 (3)	0.3038 (4)	0.0682 (10)
H20A	0.5666	0.0647	0.2840	0.102*
H20B	0.5371	0.1616	0.2163	0.102*
H20C	0.5226	0.0893	0.3363	0.102*
C21	0.32251 (10)	0.6907 (2)	0.3728 (3)	0.0411 (7)
H21	0.3375	0.6327	0.4347	0.049*
C22	0.28172 (11)	0.7229 (3)	0.4345 (3)	0.0492 (8)
H22	0.2696	0.7884	0.3833	0.059*
C23	0.24657 (10)	0.6372 (3)	0.4037 (4)	0.0510 (8)
C24	0.23644 (11)	0.5946 (3)	0.2506 (3)	0.0520 (8)
H24A	0.2054	0.6053	0.2109	0.062*
H24B	0.2420	0.5177	0.2534	0.062*
C25	0.26308 (10)	0.6470 (2)	0.1472 (3)	0.0446 (7)
H25	0.2611	0.5977	0.0641	0.054*
C26	0.24783 (10)	0.7553 (2)	0.0823 (3)	0.0470 (8)
C27	0.21257 (12)	0.8110 (3)	0.1142 (4)	0.0613 (9)
H27	0.1970	0.7822	0.1806	0.074*
C28	0.20001 (14)	0.9089 (3)	0.0493 (4)	0.0825 (12)
H28	0.1762	0.9455	0.0730	0.099*
C29	0.22233 (16)	0.9526 (3)	−0.0500 (5)	0.0910 (14)
H29	0.2141	1.0192	−0.0923	0.109*
C30	0.25681 (15)	0.8972 (4)	−0.0860 (4)	0.0827 (12)
H30	0.2719	0.9256	−0.1543	0.099*
C31	0.26915 (12)	0.7997 (3)	−0.0212 (4)	0.0644 (10)
H31	0.2924	0.7624	−0.0474	0.077*
C32	0.35415 (10)	0.7850 (2)	0.3844 (3)	0.0427 (7)
C33	0.39264 (11)	0.7851 (3)	0.4903 (3)	0.0525 (8)
H33	0.3992	0.7256	0.5513	0.063*
C34	0.42113 (12)	0.8708 (3)	0.5068 (4)	0.0656 (10)
H34	0.4466	0.8688	0.5787	0.079*
C35	0.41234 (14)	0.9586 (3)	0.4187 (5)	0.0741 (12)
H35	0.4318	1.0164	0.4298	0.089*
C36	0.37464 (15)	0.9612 (3)	0.3134 (5)	0.0749 (11)
H36	0.3686	1.0211	0.2528	0.090*
C37	0.34551 (13)	0.8754 (2)	0.2963 (4)	0.0597 (9)
H37	0.3199	0.8785	0.2249	0.072*
C38	0.33837 (10)	0.5885 (2)	0.1586 (3)	0.0439 (7)
C39	0.38335 (10)	0.5695 (3)	0.2533 (3)	0.0506 (8)
H39A	0.3802	0.5288	0.3395	0.061*
H39B	0.3967	0.6382	0.2856	0.061*
C40	0.29396 (13)	0.7496 (4)	0.5967 (4)	0.0788 (12)
H40A	0.3109	0.6916	0.6477	0.118*
H40B	0.2677	0.7594	0.6349	0.118*
H40C	0.3110	0.8146	0.6098	0.118*

	U11	U22	U33	U12	U13	U23
Cl1	0.0701 (6)	0.0429 (4)	0.0813 (6)	0.0046 (4)	0.0246 (5)	0.0002 (4)
Cl2	0.0606 (5)	0.0579 (5)	0.0667 (5)	0.0203 (4)	0.0193 (4)	−0.0063 (4)
O1	0.0668 (16)	0.109 (2)	0.0558 (15)	0.0238 (15)	0.0222 (13)	−0.0105 (14)
O2	0.0717 (17)	0.0582 (14)	0.0703 (16)	−0.0018 (12)	0.0007 (14)	−0.0201 (13)
O3	0.0627 (17)	0.100 (2)	0.0621 (16)	−0.0086 (14)	0.0277 (14)	0.0125 (14)
O4	0.0593 (15)	0.0758 (15)	0.0515 (15)	0.0092 (12)	0.0109 (12)	−0.0225 (13)
N1	0.0408 (15)	0.0484 (15)	0.0405 (15)	0.0006 (12)	0.0094 (12)	−0.0013 (11)
N2	0.0452 (15)	0.0410 (13)	0.0375 (15)	0.0034 (12)	0.0134 (13)	−0.0056 (11)
C1	0.050 (2)	0.068 (2)	0.0367 (18)	0.0147 (17)	0.0124 (16)	0.0043 (16)
C2	0.049 (2)	0.075 (2)	0.060 (2)	0.0018 (17)	0.0217 (18)	0.0043 (18)
C3	0.0388 (19)	0.0572 (19)	0.055 (2)	−0.0025 (15)	0.0105 (16)	−0.0061 (16)
C4	0.0461 (18)	0.0433 (17)	0.0394 (18)	0.0002 (14)	0.0137 (15)	0.0031 (13)
C5	0.050 (2)	0.0525 (18)	0.0387 (18)	0.0098 (15)	0.0086 (15)	−0.0024 (14)
C6	0.0353 (17)	0.061 (2)	0.0430 (19)	0.0040 (15)	0.0025 (15)	−0.0085 (15)
C7	0.054 (2)	0.076 (2)	0.050 (2)	0.0153 (18)	0.0106 (17)	−0.0104 (18)
C8	0.069 (3)	0.069 (2)	0.060 (2)	0.019 (2)	0.002 (2)	−0.005 (2)
C9	0.065 (3)	0.083 (3)	0.055 (2)	0.006 (2)	−0.003 (2)	0.014 (2)
C10	0.056 (2)	0.108 (3)	0.046 (2)	0.019 (2)	0.0111 (18)	0.009 (2)
C11	0.056 (2)	0.076 (2)	0.047 (2)	0.0232 (18)	0.0069 (17)	−0.0036 (18)
C12	0.0487 (19)	0.0378 (15)	0.049 (2)	−0.0010 (14)	0.0154 (17)	−0.0046 (14)
C13	0.069 (3)	0.072 (2)	0.047 (2)	−0.0169 (19)	0.0184 (19)	0.0010 (18)
C14	0.099 (3)	0.080 (3)	0.053 (2)	−0.034 (2)	0.037 (3)	−0.011 (2)
C15	0.069 (3)	0.065 (2)	0.091 (3)	−0.024 (2)	0.044 (3)	−0.027 (2)
C16	0.051 (2)	0.0567 (19)	0.088 (3)	−0.0036 (17)	0.018 (2)	−0.013 (2)
C17	0.049 (2)	0.0485 (18)	0.061 (2)	0.0009 (15)	0.0143 (19)	0.0016 (16)
C18	0.051 (2)	0.0435 (18)	0.053 (2)	−0.0006 (15)	0.0169 (17)	0.0006 (15)
C19	0.061 (2)	0.0439 (17)	0.068 (2)	0.0047 (15)	0.0152 (19)	−0.0038 (16)
C20	0.075 (3)	0.063 (2)	0.066 (2)	0.0087 (19)	0.013 (2)	−0.0142 (19)
C21	0.0509 (19)	0.0379 (15)	0.0357 (17)	0.0038 (14)	0.0117 (14)	0.0004 (13)
C22	0.055 (2)	0.0528 (19)	0.0436 (19)	0.0015 (16)	0.0183 (16)	−0.0069 (15)
C23	0.0430 (19)	0.058 (2)	0.055 (2)	0.0062 (16)	0.0172 (17)	0.0040 (17)
C24	0.049 (2)	0.0507 (18)	0.058 (2)	−0.0066 (15)	0.0133 (17)	−0.0029 (16)
C25	0.0441 (19)	0.0495 (18)	0.0411 (18)	−0.0006 (14)	0.0105 (15)	−0.0066 (15)
C26	0.049 (2)	0.0549 (18)	0.0374 (18)	0.0057 (15)	0.0101 (15)	−0.0041 (14)
C27	0.056 (2)	0.074 (2)	0.057 (2)	0.0151 (18)	0.0185 (18)	0.0047 (19)
C28	0.090 (3)	0.081 (3)	0.080 (3)	0.041 (2)	0.025 (2)	0.004 (2)
C29	0.125 (4)	0.069 (3)	0.080 (3)	0.035 (3)	0.023 (3)	0.020 (2)
C30	0.103 (3)	0.088 (3)	0.064 (3)	0.015 (3)	0.033 (2)	0.022 (2)
C31	0.070 (2)	0.072 (2)	0.056 (2)	0.0188 (19)	0.0251 (19)	0.0126 (19)
C32	0.054 (2)	0.0362 (16)	0.0416 (18)	0.0032 (14)	0.0196 (16)	−0.0060 (13)
C33	0.058 (2)	0.0447 (19)	0.055 (2)	0.0006 (16)	0.0115 (18)	−0.0064 (15)
C34	0.059 (2)	0.057 (2)	0.079 (3)	−0.0010 (18)	0.009 (2)	−0.021 (2)
C35	0.071 (3)	0.050 (2)	0.108 (3)	−0.015 (2)	0.034 (3)	−0.027 (2)
C36	0.093 (3)	0.042 (2)	0.097 (3)	−0.002 (2)	0.034 (3)	0.009 (2)
C37	0.069 (2)	0.0425 (18)	0.069 (2)	0.0015 (17)	0.0165 (19)	0.0029 (17)
C38	0.047 (2)	0.0411 (16)	0.0456 (19)	0.0016 (14)	0.0133 (16)	−0.0030 (15)
C39	0.055 (2)	0.0508 (19)	0.0492 (19)	0.0109 (15)	0.0166 (17)	−0.0045 (15)
C40	0.077 (3)	0.106 (3)	0.059 (2)	−0.009 (2)	0.029 (2)	−0.026 (2)

Cl1—C19	1.771 (3)	C18—C19	1.522 (4)
Cl2—C39	1.769 (3)	C19—H19A	0.97
O1—C1	1.208 (3)	C19—H19B	0.97
O2—C18	1.221 (4)	C20—H20A	0.96
O3—C23	1.198 (3)	C20—H20B	0.96
O4—C38	1.224 (3)	C20—H20C	0.96
N1—C18	1.360 (4)	C21—C32	1.518 (4)
N1—C3	1.480 (4)	C21—C22	1.543 (4)
N1—C4	1.489 (4)	C21—H21	0.98
N2—C38	1.368 (3)	C22—C23	1.510 (4)
N2—C25	1.475 (4)	C22—C40	1.521 (4)
N2—C21	1.489 (3)	C22—H22	0.98
C1—C2	1.491 (5)	C23—C24	1.496 (4)
C1—C5	1.520 (4)	C24—C25	1.534 (4)
C2—C3	1.520 (4)	C24—H24A	0.97
C2—H2A	0.97	C24—H24B	0.97
C2—H2B	0.97	C25—C26	1.511 (4)
C3—C6	1.513 (4)	C25—H25	0.98
C3—H3	0.98	C26—C27	1.376 (4)
C4—C12	1.526 (4)	C26—C31	1.387 (4)
C4—C5	1.546 (4)	C27—C28	1.379 (5)
C4—H4	0.98	C27—H27	0.93
C5—C20	1.517 (4)	C28—C29	1.373 (6)
C5—H5	0.98	C28—H28	0.93
C6—C11	1.375 (4)	C29—C30	1.368 (5)
C6—C7	1.384 (4)	C29—H29	0.93
C7—C8	1.375 (5)	C30—C31	1.373 (5)
C7—H7	0.93	C30—H30	0.93
C8—C9	1.365 (5)	C31—H31	0.93
C8—H8	0.93	C32—C37	1.385 (4)
C9—C10	1.371 (5)	C32—C33	1.390 (4)
C9—H9	0.93	C33—C34	1.373 (4)
C10—C11	1.372 (5)	C33—H33	0.93
C10—H10	0.93	C34—C35	1.360 (5)
C11—H11	0.93	C34—H34	0.93
C12—C13	1.377 (4)	C35—C36	1.370 (5)
C12—C17	1.386 (4)	C35—H35	0.93
C13—C14	1.394 (5)	C36—C37	1.386 (5)
C13—H13	0.93	C36—H36	0.93
C14—C15	1.369 (5)	C37—H37	0.93
C14—H14	0.93	C38—C39	1.515 (4)
C15—C16	1.354 (5)	C39—H39A	0.97
C15—H15	0.93	C39—H39B	0.97
C16—C17	1.366 (5)	C40—H40A	0.96
C16—H16	0.93	C40—H40B	0.96
C17—H17	0.93	C40—H40C	0.96
C18—N1—C3	117.4 (3)	C5—C20—H20C	109.5
C18—N1—C4	122.9 (2)	H20A—C20—H20C	109.5
C3—N1—C4	118.7 (2)	H20B—C20—H20C	109.5
C38—N2—C25	117.2 (2)	N2—C21—C32	113.1 (2)
C38—N2—C21	121.6 (2)	N2—C21—C22	111.3 (2)
C25—N2—C21	119.9 (2)	C32—C21—C22	109.9 (2)
O1—C1—C2	122.1 (3)	N2—C21—H21	107.4
O1—C1—C5	122.0 (3)	C32—C21—H21	107.4
C2—C1—C5	116.0 (3)	C22—C21—H21	107.4
C1—C2—C3	113.0 (3)	C23—C22—C40	111.8 (3)
C1—C2—H2A	109.0	C23—C22—C21	111.2 (2)
C3—C2—H2A	109.0	C40—C22—C21	111.4 (3)
C1—C2—H2B	109.0	C23—C22—H22	107.4
C3—C2—H2B	109.0	C40—C22—H22	107.4
H2A—C2—H2B	107.8	C21—C22—H22	107.4
N1—C3—C6	113.0 (3)	O3—C23—C24	121.7 (3)
N1—C3—C2	107.3 (3)	O3—C23—C22	122.3 (3)
C6—C3—C2	116.3 (3)	C24—C23—C22	116.0 (3)
N1—C3—H3	106.6	C23—C24—C25	114.3 (3)
C6—C3—H3	106.6	C23—C24—H24A	108.7
C2—C3—H3	106.6	C25—C24—H24A	108.7
N1—C4—C12	112.0 (2)	C23—C24—H24B	108.7
N1—C4—C5	111.4 (2)	C25—C24—H24B	108.7
C12—C4—C5	110.3 (2)	H24A—C24—H24B	107.6
N1—C4—H4	107.6	N2—C25—C26	112.6 (2)
C12—C4—H4	107.6	N2—C25—C24	107.9 (2)
C5—C4—H4	107.6	C26—C25—C24	117.7 (3)
C20—C5—C1	112.7 (3)	N2—C25—H25	105.9
C20—C5—C4	112.1 (3)	C26—C25—H25	105.9
C1—C5—C4	110.3 (2)	C24—C25—H25	105.9
C20—C5—H5	107.1	C27—C26—C31	117.4 (3)
C1—C5—H5	107.1	C27—C26—C25	124.0 (3)
C4—C5—H5	107.1	C31—C26—C25	118.5 (3)
C11—C6—C7	117.0 (3)	C26—C27—C28	121.1 (3)
C11—C6—C3	118.8 (3)	C26—C27—H27	119.5
C7—C6—C3	124.2 (3)	C28—C27—H27	119.5
C8—C7—C6	121.5 (3)	C29—C28—C27	120.5 (4)
C8—C7—H7	119.2	C29—C28—H28	119.7
C6—C7—H7	119.2	C27—C28—H28	119.7
C9—C8—C7	119.9 (3)	C30—C29—C28	119.3 (4)
C9—C8—H8	120.0	C30—C29—H29	120.3
C7—C8—H8	120.0	C28—C29—H29	120.3
C8—C9—C10	119.9 (4)	C29—C30—C31	119.9 (4)
C8—C9—H9	120.0	C29—C30—H30	120.0
C10—C9—H9	120.0	C31—C30—H30	120.0
C9—C10—C11	119.5 (3)	C30—C31—C26	121.8 (3)
C9—C10—H10	120.2	C30—C31—H31	119.1
C11—C10—H10	120.2	C26—C31—H31	119.1
C10—C11—C6	122.1 (3)	C37—C32—C33	117.3 (3)
C10—C11—H11	118.9	C37—C32—C21	122.4 (3)
C6—C11—H11	118.9	C33—C32—C21	120.2 (3)
C13—C12—C17	118.3 (3)	C34—C33—C32	121.6 (3)
C13—C12—C4	121.4 (3)	C34—C33—H33	119.2
C17—C12—C4	120.3 (3)	C32—C33—H33	119.2
C12—C13—C14	119.9 (4)	C35—C34—C33	120.4 (4)
C12—C13—H13	120.0	C35—C34—H34	119.8
C14—C13—H13	120.0	C33—C34—H34	119.8
C15—C14—C13	120.1 (3)	C34—C35—C36	119.5 (3)
C15—C14—H14	119.9	C34—C35—H35	120.3
C13—C14—H14	119.9	C36—C35—H35	120.3
C16—C15—C14	120.0 (4)	C35—C36—C37	120.6 (4)
C16—C15—H15	120.0	C35—C36—H36	119.7
C14—C15—H15	120.0	C37—C36—H36	119.7
C15—C16—C17	120.4 (4)	C32—C37—C36	120.6 (4)
C15—C16—H16	119.8	C32—C37—H37	119.7
C17—C16—H16	119.8	C36—C37—H37	119.7
C16—C17—C12	121.2 (3)	O4—C38—N2	122.5 (3)
C16—C17—H17	119.4	O4—C38—C39	121.7 (3)
C12—C17—H17	119.4	N2—C38—C39	115.8 (3)
O2—C18—N1	123.6 (3)	C38—C39—Cl2	111.4 (2)
O2—C18—C19	121.4 (3)	C38—C39—H39A	109.3
N1—C18—C19	115.1 (3)	Cl2—C39—H39A	109.3
C18—C19—Cl1	112.2 (2)	C38—C39—H39B	109.3
C18—C19—H19A	109.2	Cl2—C39—H39B	109.3
Cl1—C19—H19A	109.2	H39A—C39—H39B	108.0
C18—C19—H19B	109.2	C22—C40—H40A	109.5
Cl1—C19—H19B	109.2	C22—C40—H40B	109.5
H19A—C19—H19B	107.9	H40A—C40—H40B	109.5
C5—C20—H20A	109.5	C22—C40—H40C	109.5
C5—C20—H20B	109.5	H40A—C40—H40C	109.5
H20A—C20—H20B	109.5	H40B—C40—H40C	109.5
O1—C1—C2—C3	−166.7 (3)	C38—N2—C21—C32	73.0 (3)
C5—C1—C2—C3	13.7 (4)	C25—N2—C21—C32	−120.2 (3)
C18—N1—C3—C6	109.4 (3)	C38—N2—C21—C22	−162.7 (2)
C4—N1—C3—C6	−81.7 (3)	C25—N2—C21—C22	4.1 (3)
C18—N1—C3—C2	−121.1 (3)	N2—C21—C22—C23	45.2 (3)
C4—N1—C3—C2	47.8 (3)	C32—C21—C22—C23	171.3 (3)
C1—C2—C3—N1	−57.4 (3)	N2—C21—C22—C40	170.7 (3)
C1—C2—C3—C6	70.2 (4)	C32—C21—C22—C40	−63.2 (3)
C18—N1—C4—C12	−62.3 (3)	C40—C22—C23—O3	7.8 (5)
C3—N1—C4—C12	129.4 (3)	C21—C22—C23—O3	133.1 (3)
C18—N1—C4—C5	173.6 (3)	C40—C22—C23—C24	−172.2 (3)
C3—N1—C4—C5	5.3 (3)	C21—C22—C23—C24	−46.9 (4)
O1—C1—C5—C20	−13.2 (4)	O3—C23—C24—C25	178.8 (3)
C2—C1—C5—C20	166.4 (3)	C22—C23—C24—C25	−1.2 (4)
O1—C1—C5—C4	−139.4 (3)	C38—N2—C25—C26	−111.9 (3)
C2—C1—C5—C4	40.2 (4)	C21—N2—C25—C26	80.7 (3)
N1—C4—C5—C20	−176.3 (3)	C38—N2—C25—C24	116.5 (3)
C12—C4—C5—C20	58.6 (3)	C21—N2—C25—C24	−50.8 (3)
N1—C4—C5—C1	−49.8 (3)	C23—C24—C25—N2	48.3 (3)
C12—C4—C5—C1	−174.9 (2)	C23—C24—C25—C26	−80.4 (4)
N1—C3—C6—C11	−51.3 (4)	N2—C25—C26—C27	−124.2 (3)
C2—C3—C6—C11	−176.0 (3)	C24—C25—C26—C27	2.3 (4)
N1—C3—C6—C7	129.2 (3)	N2—C25—C26—C31	59.0 (4)
C2—C3—C6—C7	4.5 (4)	C24—C25—C26—C31	−174.5 (3)
C11—C6—C7—C8	1.8 (5)	C31—C26—C27—C28	−2.2 (5)
C3—C6—C7—C8	−178.7 (3)	C25—C26—C27—C28	−179.0 (3)
C6—C7—C8—C9	0.2 (5)	C26—C27—C28—C29	0.5 (6)
C7—C8—C9—C10	−1.8 (5)	C27—C28—C29—C30	1.1 (7)
C8—C9—C10—C11	1.4 (6)	C28—C29—C30—C31	−1.0 (7)
C9—C10—C11—C6	0.7 (6)	C29—C30—C31—C26	−0.7 (6)
C7—C6—C11—C10	−2.2 (5)	C27—C26—C31—C30	2.3 (5)
C3—C6—C11—C10	178.3 (3)	C25—C26—C31—C30	179.3 (3)
N1—C4—C12—C13	−50.8 (4)	N2—C21—C32—C37	53.2 (4)
C5—C4—C12—C13	74.0 (3)	C22—C21—C32—C37	−71.8 (4)
N1—C4—C12—C17	129.3 (3)	N2—C21—C32—C33	−129.5 (3)
C5—C4—C12—C17	−105.9 (3)	C22—C21—C32—C33	105.5 (3)
C17—C12—C13—C14	−1.3 (5)	C37—C32—C33—C34	−0.3 (4)
C4—C12—C13—C14	178.8 (3)	C21—C32—C33—C34	−177.7 (3)
C12—C13—C14—C15	0.3 (5)	C32—C33—C34—C35	−0.2 (5)
C13—C14—C15—C16	0.3 (5)	C33—C34—C35—C36	0.3 (5)
C14—C15—C16—C17	0.1 (5)	C34—C35—C36—C37	0.1 (6)
C15—C16—C17—C12	−1.1 (5)	C33—C32—C37—C36	0.7 (5)
C13—C12—C17—C16	1.8 (4)	C21—C32—C37—C36	178.0 (3)
C4—C12—C17—C16	−178.3 (3)	C35—C36—C37—C32	−0.6 (6)
C3—N1—C18—O2	−14.2 (4)	C25—N2—C38—O4	12.3 (4)
C4—N1—C18—O2	177.4 (3)	C21—N2—C38—O4	179.5 (3)
C3—N1—C18—C19	164.4 (3)	C25—N2—C38—C39	−166.5 (2)
C4—N1—C18—C19	−4.0 (4)	C21—N2—C38—C39	0.6 (4)
O2—C18—C19—Cl1	4.6 (4)	O4—C38—C39—Cl2	4.0 (4)
N1—C18—C19—Cl1	−174.0 (2)	N2—C38—C39—Cl2	−177.1 (2)