Crystal structure of 2,4-bis-(2-chloro-phen-yl)-7-tert-pent-yl-3-aza-bicyclo[3.3.1]nonan-9-one.

The title compound, C25H29Cl2NO, which is a chloro analog of 2,4-bis-(2-bromo-phen-yl)-7-(tert-pent-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one [Park, Ramkumar & Parthiban (2012). Acta Cryst. E68, o2946], exists in a twin-chair conformation with an equatorial orientation of the 2-chloro-phenyl groups. The tert-pentyl group on the cyclo-hexa-none adopts an exocyclic equatorial position and is disordered between two orientations in a ratio 0.520 (8):0.480 (8). The crystal packing shows no directional contacts beyond van der Waals contacts.

Related literature

For the synthesis, stereochemistry and biological activity of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Park et al. (2011 ▶, 2012a ▶). For a related crystal structure, see: Park et al. (2012b ▶). For the conformation of functionalized 3-aza­bicycles, see: Parthiban et al. (2010 ▶); Park et al. (2012c ▶); Padegimas & Kovacic (1972 ▶).

Experimental

Crystal data

C25H29Cl2NO

M = 430.39

Triclinic,

a = 7.6006 (3) Å

b = 10.6240 (5) Å

c = 15.1124 (7) Å

α = 106.116 (2)°

β = 99.996 (2)°

γ = 98.266 (2)°

V = 1130.54 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.928, T max = 0.955

13160 measured reflections

3789 independent reflections

2944 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.03

3789 reflections

313 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681402176X/cv5472sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402176X/cv5472Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681402176X/cv5472Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S160053681402176X/cv5472fig1.tif

View of the title mol­ecule showing the atomic numbering and 30% probability displacement ellipsoids. For clarity, only major component of the disordered group is shown.

CCDC reference: 1027325

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H29Cl2NO	V = 1130.54 (9) Å3
Mr = 430.39	Z = 2
Triclinic, P1	F(000) = 456
a = 7.6006 (3) Å	Dx = 1.264 Mg m−3
b = 10.6240 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.1124 (7) Å	µ = 0.30 mm−1
α = 106.116 (2)°	T = 298 K
β = 99.996 (2)°	Block, colourless
γ = 98.266 (2)°	0.25 × 0.20 × 0.15 mm

Bruker APEXII area-detector diffractometer	2944 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.020
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 25.0°, θmin = 2.0°
Tmin = 0.928, Tmax = 0.955	h = −9→6
13160 measured reflections	k = −12→12
3789 independent reflections	l = −17→17

Refinement on F2	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.5471P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.041
3789 reflections	Δρmax = 0.36 e Å−3
313 parameters	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.3313 (3)	0.57407 (19)	0.12669 (15)	0.0406 (5)
H1	0.2254	0.5266	0.0749	0.049*
C2	0.2630 (3)	0.6552 (2)	0.21189 (16)	0.0442 (5)
H2	0.1886	0.7138	0.1906	0.053*
C3	0.4123 (3)	0.7409 (2)	0.29862 (15)	0.0468 (5)
H3A	0.4952	0.8002	0.2787	0.056*
H3B	0.3556	0.7964	0.3432	0.056*
C4	0.5240 (3)	0.6624 (2)	0.35002 (16)	0.0466 (5)
H4	0.6008	0.6236	0.3083	0.056*
C5	0.3990 (3)	0.5446 (2)	0.36240 (16)	0.0486 (6)
H5A	0.3413	0.5789	0.4140	0.058*
H5B	0.4737	0.4851	0.3804	0.058*
C6	0.2491 (3)	0.4627 (2)	0.27445 (16)	0.0471 (5)
H6	0.1661	0.3997	0.2925	0.057*
C7	0.3167 (3)	0.38288 (19)	0.18868 (15)	0.0428 (5)
H7	0.2097	0.3330	0.1382	0.051*
C8	0.1434 (3)	0.5563 (2)	0.24180 (16)	0.0488 (6)
C9	0.4562 (3)	0.66577 (19)	0.09259 (14)	0.0380 (5)
C10	0.6447 (3)	0.6856 (2)	0.12042 (16)	0.0465 (5)
H10	0.6951	0.6381	0.1580	0.056*
C11	0.7590 (3)	0.7744 (2)	0.09362 (18)	0.0562 (6)
H11	0.8847	0.7862	0.1138	0.067*
C12	0.6891 (4)	0.8452 (2)	0.03757 (17)	0.0573 (6)
H12	0.7669	0.9052	0.0201	0.069*
C13	0.5037 (3)	0.8269 (2)	0.00741 (15)	0.0494 (6)
H13	0.4550	0.8737	−0.0312	0.059*
C14	0.3896 (3)	0.7384 (2)	0.03483 (14)	0.0419 (5)
C15	0.4261 (3)	0.28405 (19)	0.21254 (15)	0.0425 (5)
C16	0.3442 (3)	0.1555 (2)	0.20782 (16)	0.0488 (6)
C17	0.4439 (4)	0.0637 (2)	0.22588 (19)	0.0623 (7)
H17	0.3849	−0.0216	0.2213	0.075*
C18	0.6297 (4)	0.0981 (3)	0.2506 (2)	0.0695 (8)
H18	0.6979	0.0362	0.2625	0.083*
C19	0.7157 (4)	0.2251 (3)	0.2577 (2)	0.0665 (7)
H19	0.8423	0.2494	0.2755	0.080*
C20	0.6147 (3)	0.3163 (2)	0.23847 (17)	0.0532 (6)
H20	0.6748	0.4013	0.2430	0.064*
C21	0.647 (3)	0.7469 (17)	0.4380 (15)	0.072 (6)	0.520 (8)
C22	0.753 (3)	0.8725 (19)	0.4286 (14)	0.124 (8)	0.520 (8)
H22A	0.7762	0.8544	0.3663	0.186*	0.520 (8)
H22B	0.8667	0.9015	0.4745	0.186*	0.520 (8)
H22C	0.6831	0.9416	0.4389	0.186*	0.520 (8)
C23	0.565 (3)	0.805 (3)	0.5161 (11)	0.105 (7)	0.520 (8)
H23A	0.6564	0.8702	0.5660	0.157*	0.520 (8)
H23B	0.5143	0.7356	0.5393	0.157*	0.520 (8)
H23C	0.4701	0.8471	0.4944	0.157*	0.520 (8)
C24	0.777 (3)	0.668 (2)	0.4817 (17)	0.171 (5)	0.520 (8)
H24A	0.7085	0.6296	0.5198	0.205*	0.520 (8)
H24B	0.7801	0.5927	0.4283	0.205*	0.520 (8)
C25	0.9450 (13)	0.7029 (12)	0.5319 (9)	0.171 (5)	0.520 (8)
H25A	1.0225	0.7434	0.4993	0.256*	0.520 (8)
H25B	0.9861	0.6252	0.5413	0.256*	0.520 (8)
H25C	0.9494	0.7659	0.5922	0.256*	0.520 (8)
C21A	0.665 (4)	0.754 (2)	0.4492 (15)	0.076 (6)	0.480 (8)
C22A	0.799 (2)	0.6604 (15)	0.4763 (10)	0.142 (8)	0.480 (8)
H22D	0.8658	0.7005	0.5407	0.212*	0.480 (8)
H22E	0.8830	0.6503	0.4353	0.212*	0.480 (8)
H22F	0.7287	0.5741	0.4692	0.212*	0.480 (8)
C23A	0.544 (4)	0.820 (3)	0.5231 (16)	0.136 (10)	0.480 (8)
H23D	0.4741	0.8750	0.4969	0.204*	0.480 (8)
H23E	0.6245	0.8743	0.5820	0.204*	0.480 (8)
H23F	0.4636	0.7503	0.5335	0.204*	0.480 (8)
C24A	0.784 (3)	0.8687 (16)	0.4277 (14)	0.084 (5)	0.480 (8)
H24C	0.7014	0.9185	0.4028	0.101*	0.480 (8)
H24D	0.8568	0.9285	0.4879	0.101*	0.480 (8)
C25A	0.8920 (15)	0.8455 (10)	0.3726 (7)	0.128 (4)	0.480 (8)
H25D	0.9835	0.8035	0.3980	0.192*	0.480 (8)
H25E	0.9496	0.9282	0.3664	0.192*	0.480 (8)
H25F	0.8247	0.7873	0.3116	0.192*	0.480 (8)
Cl2	0.10719 (9)	0.10441 (6)	0.17580 (6)	0.0745 (2)
Cl1	0.15563 (9)	0.72003 (8)	−0.00583 (5)	0.0713 (2)
N1	0.4263 (2)	0.47552 (17)	0.15359 (13)	0.0433 (4)
O1	−0.0167 (2)	0.55371 (18)	0.24000 (15)	0.0717 (5)
H1N	0.461 (3)	0.428 (2)	0.1038 (17)	0.054 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0404 (11)	0.0351 (10)	0.0469 (12)	0.0060 (9)	0.0096 (9)	0.0147 (9)
C2	0.0461 (12)	0.0391 (11)	0.0580 (13)	0.0172 (10)	0.0191 (10)	0.0231 (10)
C3	0.0616 (14)	0.0324 (10)	0.0516 (13)	0.0109 (10)	0.0202 (11)	0.0157 (10)
C4	0.0573 (14)	0.0387 (11)	0.0478 (13)	0.0085 (10)	0.0142 (11)	0.0192 (10)
C5	0.0654 (15)	0.0404 (11)	0.0503 (13)	0.0143 (11)	0.0229 (11)	0.0224 (10)
C6	0.0508 (13)	0.0365 (11)	0.0656 (14)	0.0079 (10)	0.0296 (11)	0.0245 (10)
C7	0.0455 (12)	0.0306 (10)	0.0536 (13)	0.0040 (9)	0.0142 (10)	0.0151 (9)
C8	0.0461 (14)	0.0454 (12)	0.0600 (14)	0.0121 (10)	0.0226 (11)	0.0168 (11)
C9	0.0432 (12)	0.0318 (10)	0.0406 (11)	0.0083 (9)	0.0120 (9)	0.0119 (9)
C10	0.0440 (13)	0.0477 (12)	0.0535 (13)	0.0115 (10)	0.0130 (10)	0.0226 (10)
C11	0.0452 (13)	0.0586 (14)	0.0659 (15)	0.0032 (11)	0.0173 (12)	0.0217 (13)
C12	0.0693 (17)	0.0440 (12)	0.0609 (15)	−0.0005 (12)	0.0261 (13)	0.0192 (11)
C13	0.0719 (17)	0.0372 (11)	0.0455 (12)	0.0144 (11)	0.0191 (12)	0.0176 (10)
C14	0.0481 (12)	0.0381 (11)	0.0405 (11)	0.0124 (9)	0.0105 (9)	0.0117 (9)
C15	0.0519 (13)	0.0318 (10)	0.0481 (12)	0.0084 (9)	0.0195 (10)	0.0141 (9)
C16	0.0623 (14)	0.0350 (11)	0.0536 (13)	0.0080 (10)	0.0231 (11)	0.0160 (10)
C17	0.092 (2)	0.0373 (12)	0.0723 (17)	0.0202 (13)	0.0353 (15)	0.0262 (12)
C18	0.090 (2)	0.0608 (16)	0.0817 (19)	0.0423 (16)	0.0340 (16)	0.0373 (14)
C19	0.0578 (16)	0.0714 (17)	0.0844 (19)	0.0266 (14)	0.0247 (14)	0.0345 (15)
C20	0.0545 (15)	0.0424 (12)	0.0703 (16)	0.0131 (11)	0.0219 (12)	0.0231 (11)
C21	0.088 (9)	0.066 (9)	0.071 (9)	0.014 (8)	−0.001 (6)	0.048 (8)
C22	0.109 (12)	0.121 (12)	0.091 (10)	−0.032 (8)	−0.022 (8)	0.006 (8)
C23	0.157 (13)	0.077 (7)	0.044 (7)	0.004 (9)	−0.017 (9)	−0.004 (6)
C24	0.107 (6)	0.190 (8)	0.238 (11)	0.020 (6)	−0.016 (6)	0.142 (8)
C25	0.107 (6)	0.190 (8)	0.238 (11)	0.020 (6)	−0.016 (6)	0.142 (8)
C21A	0.088 (10)	0.059 (8)	0.044 (6)	−0.039 (7)	−0.007 (6)	0.001 (5)
C22A	0.150 (12)	0.108 (7)	0.114 (7)	−0.078 (8)	−0.109 (8)	0.088 (6)
C23A	0.219 (19)	0.100 (14)	0.074 (9)	−0.004 (12)	0.078 (11)	−0.003 (8)
C24A	0.073 (7)	0.076 (8)	0.111 (11)	−0.020 (5)	0.004 (6)	0.069 (8)
C25A	0.135 (9)	0.100 (6)	0.122 (8)	0.002 (6)	0.007 (7)	0.015 (6)
Cl2	0.0669 (4)	0.0464 (3)	0.1071 (6)	−0.0064 (3)	0.0240 (4)	0.0251 (3)
Cl1	0.0531 (4)	0.0934 (5)	0.0785 (5)	0.0225 (4)	0.0065 (3)	0.0456 (4)
N1	0.0528 (11)	0.0326 (9)	0.0536 (11)	0.0125 (8)	0.0256 (9)	0.0176 (8)
O1	0.0477 (10)	0.0753 (12)	0.1089 (15)	0.0197 (9)	0.0349 (10)	0.0412 (11)

C1—N1	1.461 (3)	C17—C18	1.364 (4)
C1—C9	1.516 (3)	C17—H17	0.9300
C1—C2	1.554 (3)	C18—C19	1.378 (4)
C1—H1	0.9800	C18—H18	0.9300
C2—C8	1.505 (3)	C19—C20	1.380 (3)
C2—C3	1.536 (3)	C19—H19	0.9300
C2—H2	0.9800	C20—H20	0.9300
C3—C4	1.534 (3)	C21—C23	1.46 (3)
C3—H3A	0.9700	C21—C22	1.51 (3)
C3—H3B	0.9700	C21—C24	1.56 (3)
C4—C21	1.454 (19)	C22—H22A	0.9600
C4—C5	1.535 (3)	C22—H22B	0.9600
C4—C21A	1.636 (19)	C22—H22C	0.9600
C4—H4	0.9800	C23—H23A	0.9600
C5—C6	1.539 (3)	C23—H23B	0.9600
C5—H5A	0.9700	C23—H23C	0.9600
C5—H5B	0.9700	C24—C25	1.309 (18)
C6—C8	1.497 (3)	C24—H24A	0.9700
C6—C7	1.552 (3)	C24—H24B	0.9700
C6—H6	0.9800	C25—H25A	0.9600
C7—N1	1.467 (3)	C25—H25B	0.9600
C7—C15	1.511 (3)	C25—H25C	0.9600
C7—H7	0.9800	C21A—C24A	1.55 (3)
C8—O1	1.209 (3)	C21A—C22A	1.61 (3)
C9—C10	1.388 (3)	C21A—C23A	1.64 (4)
C9—C14	1.395 (3)	C22A—H22D	0.9600
C10—C11	1.381 (3)	C22A—H22E	0.9600
C10—H10	0.9300	C22A—H22F	0.9600
C11—C12	1.370 (4)	C23A—H23D	0.9600
C11—H11	0.9300	C23A—H23E	0.9600
C12—C13	1.371 (3)	C23A—H23F	0.9600
C12—H12	0.9300	C24A—C25A	1.27 (3)
C13—C14	1.384 (3)	C24A—H24C	0.9700
C13—H13	0.9300	C24A—H24D	0.9700
C14—Cl1	1.742 (2)	C25A—H25D	0.9600
C15—C20	1.384 (3)	C25A—H25E	0.9600
C15—C16	1.394 (3)	C25A—H25F	0.9600
C16—C17	1.374 (3)	N1—H1N	0.89 (2)
C16—Cl2	1.745 (2)
N1—C1—C9	110.16 (16)	C16—C17—H17	120.1
N1—C1—C2	109.81 (17)	C17—C18—C19	119.6 (2)
C9—C1—C2	111.03 (16)	C17—C18—H18	120.2
N1—C1—H1	108.6	C19—C18—H18	120.2
C9—C1—H1	108.6	C18—C19—C20	120.3 (3)
C2—C1—H1	108.6	C18—C19—H19	119.9
C8—C2—C3	108.14 (18)	C20—C19—H19	119.9
C8—C2—C1	107.25 (16)	C19—C20—C15	121.5 (2)
C3—C2—C1	115.74 (18)	C19—C20—H20	119.3
C8—C2—H2	108.5	C15—C20—H20	119.3
C3—C2—H2	108.5	C4—C21—C23	117.1 (18)
C1—C2—H2	108.5	C4—C21—C22	113.0 (14)
C4—C3—C2	115.32 (17)	C23—C21—C22	100.3 (18)
C4—C3—H3A	108.4	C4—C21—C24	111.8 (14)
C2—C3—H3A	108.4	C23—C21—C24	102.4 (18)
C4—C3—H3B	108.4	C22—C21—C24	111 (2)
C2—C3—H3B	108.4	C21—C22—H22A	109.4
H3A—C3—H3B	107.5	C21—C22—H22B	109.5
C21—C4—C3	113.1 (6)	H22A—C22—H22B	109.5
C21—C4—C5	112.9 (9)	C21—C22—H22C	109.5
C3—C4—C5	110.78 (19)	H22A—C22—H22C	109.5
C3—C4—C21A	114.5 (8)	H22B—C22—H22C	109.5
C5—C4—C21A	112.2 (9)	C21—C23—H23A	109.5
C21—C4—H4	106.5	C21—C23—H23B	109.5
C3—C4—H4	106.5	H23A—C23—H23B	109.5
C5—C4—H4	106.5	C21—C23—H23C	109.4
C4—C5—C6	115.05 (18)	H23A—C23—H23C	109.5
C4—C5—H5A	108.5	H23B—C23—H23C	109.5
C6—C5—H5A	108.5	C25—C24—C21	132.5 (17)
C4—C5—H5B	108.5	C25—C24—H24A	103.9
C6—C5—H5B	108.5	C21—C24—H24A	103.9
H5A—C5—H5B	107.5	C25—C24—H24B	104.4
C8—C6—C5	108.55 (17)	C21—C24—H24B	104.3
C8—C6—C7	107.09 (18)	H24A—C24—H24B	105.5
C5—C6—C7	115.73 (18)	C24—C25—H25A	109.3
C8—C6—H6	108.4	C24—C25—H25B	109.3
C5—C6—H6	108.4	H25A—C25—H25B	109.5
C7—C6—H6	108.4	C24—C25—H25C	109.8
N1—C7—C15	109.85 (17)	H25A—C25—H25C	109.5
N1—C7—C6	109.86 (16)	H25B—C25—H25C	109.5
C15—C7—C6	112.34 (18)	C24A—C21A—C22A	106 (2)
N1—C7—H7	108.2	C24A—C21A—C4	107.5 (15)
C15—C7—H7	108.2	C22A—C21A—C4	105.6 (13)
C6—C7—H7	108.2	C24A—C21A—C23A	108.6 (19)
O1—C8—C6	124.7 (2)	C22A—C21A—C23A	120.0 (18)
O1—C8—C2	124.2 (2)	C4—C21A—C23A	108.1 (18)
C6—C8—C2	111.14 (18)	C21A—C22A—H22D	109.6
C10—C9—C14	116.29 (18)	C21A—C22A—H22E	109.3
C10—C9—C1	121.34 (18)	H22D—C22A—H22E	109.5
C14—C9—C1	122.33 (18)	C21A—C22A—H22F	109.5
C11—C10—C9	121.6 (2)	H22D—C22A—H22F	109.5
C11—C10—H10	119.2	H22E—C22A—H22F	109.5
C9—C10—H10	119.2	C21A—C23A—H23D	109.5
C12—C11—C10	120.7 (2)	C21A—C23A—H23E	109.5
C12—C11—H11	119.7	H23D—C23A—H23E	109.5
C10—C11—H11	119.7	C21A—C23A—H23F	109.4
C11—C12—C13	119.5 (2)	H23D—C23A—H23F	109.5
C11—C12—H12	120.2	H23E—C23A—H23F	109.5
C13—C12—H12	120.2	C25A—C24A—C21A	121.8 (19)
C12—C13—C14	119.6 (2)	C25A—C24A—H24C	106.9
C12—C13—H13	120.2	C21A—C24A—H24C	106.9
C14—C13—H13	120.2	C25A—C24A—H24D	106.9
C13—C14—C9	122.3 (2)	C21A—C24A—H24D	106.9
C13—C14—Cl1	117.25 (17)	H24C—C24A—H24D	106.7
C9—C14—Cl1	120.43 (16)	C24A—C25A—H25D	109.5
C20—C15—C16	116.5 (2)	C24A—C25A—H25E	109.5
C20—C15—C7	121.22 (18)	H25D—C25A—H25E	109.5
C16—C15—C7	122.3 (2)	C24A—C25A—H25F	109.5
C17—C16—C15	122.3 (2)	H25D—C25A—H25F	109.5
C17—C16—Cl2	117.35 (18)	H25E—C25A—H25F	109.5
C15—C16—Cl2	120.29 (18)	C1—N1—C7	114.20 (16)
C18—C17—C16	119.8 (2)	C1—N1—H1N	108.7 (16)
C18—C17—H17	120.1	C7—N1—H1N	108.5 (15)
N1—C1—C2—C8	−56.9 (2)	C6—C7—C15—C20	−95.7 (2)
C9—C1—C2—C8	−179.01 (17)	N1—C7—C15—C16	−151.6 (2)
N1—C1—C2—C3	63.8 (2)	C6—C7—C15—C16	85.8 (2)
C9—C1—C2—C3	−58.2 (2)	C20—C15—C16—C17	−1.3 (3)
C8—C2—C3—C4	53.9 (2)	C7—C15—C16—C17	177.4 (2)
C1—C2—C3—C4	−66.4 (2)	C20—C15—C16—Cl2	−179.97 (17)
C2—C3—C4—C21	−172.6 (12)	C7—C15—C16—Cl2	−1.3 (3)
C2—C3—C4—C5	−44.7 (2)	C15—C16—C17—C18	0.8 (4)
C2—C3—C4—C21A	−172.9 (11)	Cl2—C16—C17—C18	179.6 (2)
C21—C4—C5—C6	172.3 (9)	C16—C17—C18—C19	0.4 (4)
C3—C4—C5—C6	44.4 (2)	C17—C18—C19—C20	−1.1 (4)
C21A—C4—C5—C6	173.7 (10)	C18—C19—C20—C15	0.6 (4)
C4—C5—C6—C8	−53.6 (2)	C16—C15—C20—C19	0.6 (3)
C4—C5—C6—C7	66.8 (2)	C7—C15—C20—C19	−178.1 (2)
C8—C6—C7—N1	57.4 (2)	C3—C4—C21—C23	70.0 (17)
C5—C6—C7—N1	−63.8 (2)	C5—C4—C21—C23	−56.8 (16)
C8—C6—C7—C15	−179.99 (17)	C21A—C4—C21—C23	−120 (81)
C5—C6—C7—C15	58.8 (2)	C3—C4—C21—C22	−46 (2)
C5—C6—C8—O1	−116.6 (3)	C5—C4—C21—C22	−172.5 (16)
C7—C6—C8—O1	117.7 (2)	C21A—C4—C21—C22	125 (82)
C5—C6—C8—C2	63.0 (2)	C3—C4—C21—C24	−172.4 (14)
C7—C6—C8—C2	−62.6 (2)	C5—C4—C21—C24	61 (2)
C3—C2—C8—O1	116.6 (3)	C21A—C4—C21—C24	−2 (79)
C1—C2—C8—O1	−117.9 (2)	C4—C21—C24—C25	148 (3)
C3—C2—C8—C6	−63.0 (2)	C23—C21—C24—C25	−86 (3)
C1—C2—C8—C6	62.4 (2)	C22—C21—C24—C25	20 (4)
N1—C1—C9—C10	−23.9 (3)	C21—C4—C21A—C24A	−63 (79)
C2—C1—C9—C10	97.9 (2)	C3—C4—C21A—C24A	−53 (2)
N1—C1—C9—C14	158.49 (18)	C5—C4—C21A—C24A	179.7 (14)
C2—C1—C9—C14	−79.6 (2)	C21—C4—C21A—C22A	−176 (100)
C14—C9—C10—C11	1.2 (3)	C3—C4—C21A—C22A	−166.3 (11)
C1—C9—C10—C11	−176.5 (2)	C5—C4—C21A—C22A	66.3 (17)
C9—C10—C11—C12	−0.6 (4)	C21—C4—C21A—C23A	54 (80)
C10—C11—C12—C13	−0.4 (4)	C3—C4—C21A—C23A	64.1 (18)
C11—C12—C13—C14	0.7 (3)	C5—C4—C21A—C23A	−63.3 (17)
C12—C13—C14—C9	−0.1 (3)	C22A—C21A—C24A—C25A	49 (2)
C12—C13—C14—Cl1	179.93 (17)	C4—C21A—C24A—C25A	−64 (2)
C10—C9—C14—C13	−0.8 (3)	C23A—C21A—C24A—C25A	179.7 (17)
C1—C9—C14—C13	176.83 (18)	C9—C1—N1—C7	179.34 (17)
C10—C9—C14—Cl1	179.14 (15)	C2—C1—N1—C7	56.8 (2)
C1—C9—C14—Cl1	−3.2 (3)	C15—C7—N1—C1	178.90 (17)
N1—C7—C15—C20	27.0 (3)	C6—C7—N1—C1	−57.0 (2)