1-(2,2-Di-chloro-acet-yl)-3-ethyl-2,6-di-phenyl-piperidin-4-one.

The asymmetric unit of the title compound, C21H21Cl2NO2, contains two independent mol-ecules that show similar geometrical features. The piperidine ring adopts a distorted boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring are oriented at angles of 65.4 (1) [64.7 (2)°] and 89.2 (1)° [86.3 (2)°] with respect to the least-squares plane of the piperidine ring. In the crystal, adjacent mol-ecules are linked by a network of C-H⋯O inter-actions, forming a C(6) chain along the c-axis direction.

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009 ▶); Nalanishi et al. (1974 ▶); Michael (2001 ▶); Pinder (1992 ▶); Rubiralta et al. (1991 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C21H21Cl2NO2

M = 390.29

Monoclinic,

a = 17.4615 (13) Å

b = 19.0291 (15) Å

c = 11.9501 (9) Å

β = 91.825 (5)°

V = 3968.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.928, T max = 0.940

36640 measured reflections

9905 independent reflections

5029 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.175

S = 1.00

9905 reflections

471 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010957/ng5321sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010957/ng5321Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010957/ng5321Isup3.cml

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

C21H21Cl2NO2	F(000) = 1632
Mr = 390.29	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5029 reflections
a = 17.4615 (13) Å	θ = 1.2–28.5°
b = 19.0291 (15) Å	µ = 0.34 mm−1
c = 11.9501 (9) Å	T = 293 K
β = 91.825 (5)°	Block, yellow
V = 3968.7 (5) Å3	0.22 × 0.20 × 0.18 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	9905 independent reflections
Radiation source: fine-focus sealed tube	5029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω and φ scans	θmax = 28.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −23→22
Tmin = 0.928, Tmax = 0.940	k = −25→25
36640 measured reflections	l = −15→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0716P)2 + 1.3041P] where P = (Fo2 + 2Fc2)/3
9905 reflections	(Δ/σ)max = 0.001
471 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.44 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.

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.

	x	y	z	Uiso*/Ueq
C2'	0.75368 (14)	0.67575 (13)	0.9369 (2)	0.0483 (6)
H2'	0.7482	0.7032	1.0055	0.058*
C2	0.56922 (13)	0.31595 (12)	0.33385 (18)	0.0395 (5)
H2	0.5610	0.2915	0.2623	0.047*
C3'	0.70448 (15)	0.71253 (14)	0.8467 (2)	0.0547 (7)
H3'	0.6505	0.7058	0.8638	0.066*
C3	0.53120 (14)	0.27084 (12)	0.42207 (19)	0.0426 (5)
H3	0.4757	0.2722	0.4077	0.051*
C4	0.54816 (14)	0.30054 (12)	0.5380 (2)	0.0445 (6)
C4'	0.71760 (15)	0.68289 (14)	0.7315 (2)	0.0548 (7)
C5	0.61719 (14)	0.34645 (13)	0.54913 (19)	0.0465 (6)
H5A	0.6365	0.3437	0.6260	0.056*
H5B	0.6011	0.3946	0.5357	0.056*
C5'	0.78880 (14)	0.64026 (15)	0.7192 (2)	0.0522 (6)
H5'1	0.8029	0.6420	0.6414	0.063*
H5'2	0.7770	0.5917	0.7365	0.063*
C6'	0.85851 (14)	0.66251 (13)	0.79195 (18)	0.0448 (6)
H6'	0.8805	0.7044	0.7577	0.054*
C6	0.68376 (13)	0.33050 (12)	0.47226 (18)	0.0407 (5)
H6	0.7091	0.2875	0.4992	0.049*
C7	0.74120 (14)	0.39014 (13)	0.48152 (19)	0.0445 (6)
C7'	0.91814 (14)	0.60476 (14)	0.7896 (2)	0.0500 (6)
C8	0.80352 (18)	0.38388 (17)	0.5544 (2)	0.0701 (8)
H8	0.8120	0.3418	0.5924	0.084*
C8'	0.97601 (17)	0.60923 (18)	0.7143 (3)	0.0732 (9)
H8'	0.9792	0.6486	0.6687	0.088*
C9'	1.0291 (2)	0.5564 (3)	0.7056 (4)	0.1019 (14)
H9'	1.0679	0.5602	0.6543	0.122*
C9	0.8536 (2)	0.4392 (2)	0.5716 (3)	0.0848 (10)
H9	0.8952	0.4341	0.6216	0.102*
C10'	1.0252 (2)	0.4985 (3)	0.7719 (4)	0.1046 (15)
H10'	1.0611	0.4627	0.7657	0.126*
C10	0.84274 (19)	0.50106 (19)	0.5162 (3)	0.0758 (9)
H10	0.8761	0.5386	0.5289	0.091*
C11	0.7828 (2)	0.50713 (17)	0.4426 (3)	0.0823 (10)
H11	0.7758	0.5488	0.4029	0.099*
C11'	0.9687 (3)	0.4928 (2)	0.8474 (3)	0.1001 (13)
H11'	0.9662	0.4534	0.8932	0.120*
C12	0.73198 (18)	0.45266 (15)	0.4252 (3)	0.0693 (8)
H12	0.6908	0.4583	0.3747	0.083*
C12'	0.9150 (2)	0.54601 (17)	0.8556 (3)	0.0777 (9)
H12'	0.8762	0.5418	0.9067	0.093*
C13'	0.73454 (14)	0.60042 (14)	0.9668 (2)	0.0508 (6)
C13	0.53655 (14)	0.38928 (12)	0.31778 (19)	0.0432 (5)
C14'	0.77351 (17)	0.56980 (16)	1.0579 (2)	0.0634 (7)
H14'	0.8075	0.5970	1.1008	0.076*
C14	0.57078 (15)	0.43437 (14)	0.2430 (2)	0.0542 (6)
H14	0.6127	0.4189	0.2037	0.065*
C15	0.54368 (19)	0.50191 (15)	0.2260 (2)	0.0667 (8)
H15	0.5677	0.5317	0.1764	0.080*
C15'	0.76317 (19)	0.50055 (18)	1.0861 (3)	0.0743 (9)
H15'	0.7903	0.4814	1.1471	0.089*
C16	0.48117 (19)	0.52479 (16)	0.2825 (3)	0.0698 (8)
H16	0.4634	0.5705	0.2725	0.084*
C16'	0.7127 (2)	0.45959 (18)	1.0242 (3)	0.0764 (9)
H16'	0.7064	0.4123	1.0413	0.092*
C17	0.44518 (18)	0.48050 (15)	0.3530 (3)	0.0685 (8)
H17	0.4017	0.4957	0.3889	0.082*
C17'	0.6718 (2)	0.48940 (19)	0.9369 (3)	0.0831 (10)
H17'	0.6366	0.4623	0.8958	0.100*
C18	0.47247 (15)	0.41297 (14)	0.3722 (2)	0.0539 (6)
H18	0.4478	0.3835	0.4217	0.065*
C18'	0.68197 (17)	0.55937 (17)	0.9089 (3)	0.0673 (8)
H18'	0.6529	0.5788	0.8501	0.081*
C19'	0.72176 (19)	0.79250 (16)	0.8463 (3)	0.0743 (9)
H19A	0.7229	0.8093	0.9230	0.089*
H19B	0.7724	0.7997	0.8171	0.089*
C19	0.55729 (16)	0.19375 (13)	0.4187 (2)	0.0510 (6)
H19C	0.5588	0.1785	0.3414	0.061*
H19D	0.6088	0.1902	0.4511	0.061*
C20	0.50454 (18)	0.14531 (14)	0.4820 (2)	0.0640 (7)
H20A	0.5051	0.1585	0.5595	0.096*
H20B	0.5219	0.0977	0.4754	0.096*
H20C	0.4533	0.1491	0.4509	0.096*
C20'	0.6652 (2)	0.83623 (19)	0.7787 (3)	0.0905 (11)
H20D	0.6618	0.8189	0.7033	0.136*
H20E	0.6820	0.8843	0.7783	0.136*
H20F	0.6158	0.8334	0.8114	0.136*
C21'	0.88364 (15)	0.71449 (14)	0.9815 (2)	0.0545 (7)
C21	0.69852 (14)	0.29727 (13)	0.2715 (2)	0.0438 (5)
C22	0.78180 (14)	0.27937 (15)	0.3034 (2)	0.0562 (7)
H22	0.7985	0.3075	0.3685	0.067*
C22'	0.96346 (16)	0.73251 (16)	0.9400 (2)	0.0627 (8)
H22'	0.9753	0.7022	0.8765	0.075*
N1'	0.83558 (11)	0.68196 (10)	0.90685 (16)	0.0430 (5)
N1	0.65366 (11)	0.31767 (9)	0.35573 (15)	0.0389 (4)
O1'	0.67356 (12)	0.69236 (13)	0.65272 (18)	0.0795 (6)
O1	0.50727 (11)	0.28989 (10)	0.61640 (15)	0.0603 (5)
O2'	0.86636 (12)	0.73129 (13)	1.07511 (17)	0.0803 (7)
O2	0.67618 (10)	0.29028 (10)	0.17464 (14)	0.0577 (5)
Cl1'	0.96162 (6)	0.82083 (5)	0.89659 (10)	0.1063 (4)
Cl1	0.84132 (5)	0.29718 (5)	0.19055 (8)	0.0855 (3)
Cl2	0.78382 (5)	0.18921 (4)	0.33926 (7)	0.0781 (3)
Cl2'	1.03240 (5)	0.72012 (6)	1.04814 (9)	0.0994 (3)

	U11	U22	U33	U12	U13	U23
C2'	0.0476 (14)	0.0536 (16)	0.0442 (13)	0.0010 (11)	0.0076 (10)	−0.0025 (11)
C2	0.0465 (13)	0.0371 (13)	0.0346 (12)	0.0006 (10)	−0.0015 (9)	−0.0047 (9)
C3'	0.0462 (15)	0.0575 (17)	0.0607 (16)	0.0018 (12)	0.0056 (11)	0.0051 (13)
C3	0.0484 (14)	0.0377 (13)	0.0417 (13)	0.0022 (10)	0.0023 (10)	−0.0017 (10)
C4	0.0542 (15)	0.0382 (13)	0.0413 (13)	0.0127 (11)	0.0064 (10)	0.0001 (10)
C4'	0.0475 (15)	0.0567 (17)	0.0596 (17)	−0.0098 (12)	−0.0053 (12)	0.0081 (13)
C5	0.0628 (16)	0.0429 (14)	0.0339 (12)	0.0063 (12)	0.0014 (10)	−0.0066 (10)
C5'	0.0570 (16)	0.0575 (17)	0.0418 (13)	−0.0030 (13)	−0.0023 (11)	−0.0031 (12)
C6'	0.0501 (14)	0.0471 (14)	0.0373 (12)	−0.0030 (11)	0.0040 (10)	−0.0006 (10)
C6	0.0519 (14)	0.0365 (13)	0.0332 (11)	0.0030 (10)	−0.0033 (9)	−0.0020 (9)
C7	0.0543 (15)	0.0436 (14)	0.0354 (12)	−0.0001 (11)	−0.0020 (10)	−0.0084 (10)
C7'	0.0510 (15)	0.0590 (17)	0.0399 (13)	0.0004 (12)	0.0005 (10)	−0.0086 (12)
C8	0.083 (2)	0.070 (2)	0.0563 (17)	−0.0106 (17)	−0.0196 (15)	0.0026 (15)
C8'	0.0600 (18)	0.082 (2)	0.078 (2)	−0.0036 (16)	0.0163 (15)	−0.0175 (17)
C9'	0.065 (2)	0.121 (4)	0.122 (3)	0.008 (2)	0.020 (2)	−0.052 (3)
C9	0.082 (2)	0.102 (3)	0.069 (2)	−0.023 (2)	−0.0250 (17)	−0.013 (2)
C10'	0.080 (3)	0.107 (3)	0.124 (4)	0.041 (2)	−0.029 (2)	−0.057 (3)
C10	0.075 (2)	0.065 (2)	0.087 (2)	−0.0167 (17)	0.0042 (18)	−0.0323 (19)
C11	0.085 (2)	0.0466 (18)	0.114 (3)	−0.0094 (17)	−0.013 (2)	0.0011 (18)
C11'	0.129 (3)	0.083 (3)	0.088 (3)	0.046 (3)	−0.010 (2)	−0.007 (2)
C12	0.070 (2)	0.0474 (17)	0.089 (2)	−0.0043 (14)	−0.0236 (16)	0.0057 (15)
C12'	0.098 (2)	0.073 (2)	0.0621 (19)	0.0297 (19)	0.0124 (16)	0.0063 (16)
C13'	0.0490 (15)	0.0573 (16)	0.0468 (14)	−0.0031 (12)	0.0101 (11)	0.0041 (12)
C13	0.0514 (14)	0.0401 (13)	0.0374 (12)	0.0008 (11)	−0.0079 (10)	−0.0011 (10)
C14'	0.0730 (19)	0.068 (2)	0.0495 (16)	−0.0082 (15)	0.0004 (13)	0.0079 (14)
C14	0.0627 (17)	0.0513 (16)	0.0481 (14)	0.0032 (13)	−0.0053 (12)	0.0071 (12)
C15	0.088 (2)	0.0491 (17)	0.0618 (18)	−0.0020 (16)	−0.0123 (16)	0.0153 (14)
C15'	0.084 (2)	0.079 (2)	0.0598 (18)	−0.0006 (18)	0.0047 (16)	0.0254 (17)
C16	0.094 (2)	0.0417 (16)	0.072 (2)	0.0169 (16)	−0.0134 (17)	0.0017 (15)
C16'	0.087 (2)	0.066 (2)	0.077 (2)	−0.0142 (18)	0.0154 (18)	0.0180 (17)
C17	0.080 (2)	0.0495 (17)	0.076 (2)	0.0179 (15)	−0.0008 (16)	−0.0094 (15)
C17'	0.090 (2)	0.076 (2)	0.083 (2)	−0.0334 (19)	−0.0022 (19)	0.0125 (19)
C18	0.0626 (17)	0.0456 (15)	0.0536 (15)	0.0053 (13)	0.0018 (12)	−0.0013 (12)
C18'	0.0635 (18)	0.072 (2)	0.0665 (18)	−0.0177 (16)	−0.0031 (14)	0.0155 (16)
C19'	0.078 (2)	0.0592 (19)	0.085 (2)	0.0062 (16)	−0.0018 (17)	0.0047 (17)
C19	0.0650 (17)	0.0385 (14)	0.0496 (15)	0.0041 (12)	0.0052 (12)	−0.0018 (11)
C20	0.083 (2)	0.0454 (16)	0.0637 (18)	−0.0069 (14)	0.0018 (14)	0.0047 (14)
C20'	0.077 (2)	0.076 (2)	0.119 (3)	0.0138 (18)	0.008 (2)	0.030 (2)
C21'	0.0580 (16)	0.0532 (16)	0.0520 (15)	0.0002 (13)	−0.0031 (12)	−0.0140 (13)
C21	0.0490 (14)	0.0409 (13)	0.0417 (13)	−0.0037 (11)	0.0041 (10)	−0.0083 (10)
C22	0.0491 (15)	0.0607 (18)	0.0590 (16)	−0.0012 (13)	0.0048 (12)	−0.0228 (13)
C22'	0.0569 (17)	0.0647 (19)	0.0661 (18)	−0.0093 (14)	−0.0053 (13)	−0.0183 (14)
N1'	0.0466 (11)	0.0438 (12)	0.0388 (10)	−0.0011 (9)	0.0040 (8)	−0.0037 (9)
N1	0.0469 (11)	0.0368 (11)	0.0329 (10)	0.0015 (8)	−0.0019 (8)	−0.0050 (8)
O1'	0.0639 (13)	0.1041 (18)	0.0690 (14)	0.0004 (12)	−0.0230 (10)	0.0063 (12)
O1	0.0666 (12)	0.0679 (13)	0.0472 (10)	0.0088 (9)	0.0160 (9)	0.0014 (9)
O2'	0.0758 (14)	0.1051 (18)	0.0600 (13)	−0.0062 (12)	0.0022 (10)	−0.0376 (12)
O2	0.0613 (11)	0.0755 (13)	0.0363 (10)	−0.0051 (9)	0.0038 (8)	−0.0140 (9)
Cl1'	0.1115 (8)	0.0779 (6)	0.1289 (9)	−0.0250 (5)	−0.0043 (6)	0.0173 (6)
Cl1	0.0628 (5)	0.0953 (6)	0.1002 (6)	−0.0129 (4)	0.0303 (4)	−0.0139 (5)
Cl2	0.0760 (5)	0.0715 (5)	0.0868 (6)	0.0192 (4)	0.0013 (4)	0.0032 (4)
Cl2'	0.0690 (6)	0.1191 (8)	0.1083 (7)	−0.0001 (5)	−0.0281 (5)	−0.0051 (6)

C2'—N1'	1.490 (3)	C11'—H11'	0.9300
C2'—C13'	1.517 (4)	C12—H12	0.9300
C2'—C3'	1.527 (4)	C12'—H12'	0.9300
C2'—H2'	0.9800	C13'—C18'	1.375 (4)
C2—N1	1.489 (3)	C13'—C14'	1.393 (4)
C2—C13	1.517 (3)	C13—C18	1.387 (3)
C2—C3	1.528 (3)	C13—C14	1.388 (3)
C2—H2	0.9800	C14'—C15'	1.374 (4)
C3'—C4'	1.512 (4)	C14'—H14'	0.9300
C3'—C19'	1.551 (4)	C14—C15	1.382 (4)
C3'—H3'	0.9800	C14—H14	0.9300
C3—C4	1.516 (3)	C15—C16	1.372 (4)
C3—C19	1.537 (3)	C15—H15	0.9300
C3—H3	0.9800	C15'—C16'	1.376 (5)
C4—O1	1.213 (3)	C15'—H15'	0.9300
C4—C5	1.491 (4)	C16—C17	1.360 (4)
C4'—O1'	1.210 (3)	C16—H16	0.9300
C4'—C5'	1.496 (4)	C16'—C17'	1.368 (5)
C5—C6	1.535 (3)	C16'—H16'	0.9300
C5—H5A	0.9700	C17—C18	1.387 (4)
C5—H5B	0.9700	C17—H17	0.9300
C5'—C6'	1.533 (3)	C17'—C18'	1.386 (4)
C5'—H5'1	0.9700	C17'—H17'	0.9300
C5'—H5'2	0.9700	C18—H18	0.9300
C6'—N1'	1.489 (3)	C18'—H18'	0.9300
C6'—C7'	1.515 (4)	C19'—C20'	1.506 (4)
C6'—H6'	0.9800	C19'—H19A	0.9700
C6—N1	1.493 (3)	C19'—H19B	0.9700
C6—C7	1.516 (3)	C19—C20	1.521 (4)
C6—H6	0.9800	C19—H19C	0.9700
C7—C12	1.374 (4)	C19—H19D	0.9700
C7—C8	1.377 (4)	C20—H20A	0.9600
C7'—C12'	1.370 (4)	C20—H20B	0.9600
C7'—C8'	1.377 (4)	C20—H20C	0.9600
C8—C9	1.379 (4)	C20'—H20D	0.9600
C8—H8	0.9300	C20'—H20E	0.9600
C8'—C9'	1.375 (5)	C20'—H20F	0.9600
C8'—H8'	0.9300	C21'—O2'	1.210 (3)
C9'—C10'	1.360 (6)	C21'—N1'	1.355 (3)
C9'—H9'	0.9300	C21'—C22'	1.533 (4)
C9—C10	1.362 (5)	C21—O2	1.217 (3)
C9—H9	0.9300	C21—N1	1.352 (3)
C10'—C11'	1.362 (6)	C21—C22	1.530 (4)
C10'—H10'	0.9300	C22—Cl1	1.762 (3)
C10—C11	1.350 (5)	C22—Cl2	1.768 (3)
C10—H10	0.9300	C22—H22	0.9800
C11—C12	1.376 (4)	C22'—Cl2'	1.753 (3)
C11—H11	0.9300	C22'—Cl1'	1.759 (3)
C11'—C12'	1.387 (5)	C22'—H22'	0.9800
N1'—C2'—C13'	110.6 (2)	C7'—C12'—C11'	121.0 (3)
N1'—C2'—C3'	108.43 (19)	C7'—C12'—H12'	119.5
C13'—C2'—C3'	118.4 (2)	C11'—C12'—H12'	119.5
N1'—C2'—H2'	106.2	C18'—C13'—C14'	117.2 (3)
C13'—C2'—H2'	106.2	C18'—C13'—C2'	124.5 (2)
C3'—C2'—H2'	106.2	C14'—C13'—C2'	118.3 (2)
N1—C2—C13	111.60 (18)	C18—C13—C14	118.1 (2)
N1—C2—C3	109.92 (18)	C18—C13—C2	123.0 (2)
C13—C2—C3	115.73 (19)	C14—C13—C2	118.8 (2)
N1—C2—H2	106.3	C15'—C14'—C13'	121.9 (3)
C13—C2—H2	106.3	C15'—C14'—H14'	119.0
C3—C2—H2	106.3	C13'—C14'—H14'	119.0
C4'—C3'—C2'	112.0 (2)	C15—C14—C13	121.1 (3)
C4'—C3'—C19'	109.2 (2)	C15—C14—H14	119.4
C2'—C3'—C19'	110.3 (2)	C13—C14—H14	119.4
C4'—C3'—H3'	108.5	C16—C15—C14	119.8 (3)
C2'—C3'—H3'	108.5	C16—C15—H15	120.1
C19'—C3'—H3'	108.5	C14—C15—H15	120.1
C4—C3—C2	110.14 (19)	C14'—C15'—C16'	119.9 (3)
C4—C3—C19	109.3 (2)	C14'—C15'—H15'	120.1
C2—C3—C19	112.50 (19)	C16'—C15'—H15'	120.1
C4—C3—H3	108.3	C17—C16—C15	119.9 (3)
C2—C3—H3	108.3	C17—C16—H16	120.0
C19—C3—H3	108.3	C15—C16—H16	120.0
O1—C4—C5	121.5 (2)	C17'—C16'—C15'	119.0 (3)
O1—C4—C3	122.7 (2)	C17'—C16'—H16'	120.5
C5—C4—C3	115.7 (2)	C15'—C16'—H16'	120.5
O1'—C4'—C5'	121.0 (3)	C16—C17—C18	120.9 (3)
O1'—C4'—C3'	122.8 (3)	C16—C17—H17	119.6
C5'—C4'—C3'	116.2 (2)	C18—C17—H17	119.6
C4—C5—C6	117.13 (19)	C16'—C17'—C18'	121.0 (3)
C4—C5—H5A	108.0	C16'—C17'—H17'	119.5
C6—C5—H5A	108.0	C18'—C17'—H17'	119.5
C4—C5—H5B	108.0	C17—C18—C13	120.1 (3)
C6—C5—H5B	108.0	C17—C18—H18	120.0
H5A—C5—H5B	107.3	C13—C18—H18	120.0
C4'—C5'—C6'	116.3 (2)	C13'—C18'—C17'	120.8 (3)
C4'—C5'—H5'1	108.2	C13'—C18'—H18'	119.6
C6'—C5'—H5'1	108.2	C17'—C18'—H18'	119.6
C4'—C5'—H5'2	108.2	C20'—C19'—C3'	114.8 (3)
C6'—C5'—H5'2	108.2	C20'—C19'—H19A	108.6
H5'1—C5'—H5'2	107.4	C3'—C19'—H19A	108.6
N1'—C6'—C7'	113.72 (19)	C20'—C19'—H19B	108.6
N1'—C6'—C5'	111.07 (19)	C3'—C19'—H19B	108.6
C7'—C6'—C5'	108.9 (2)	H19A—C19'—H19B	107.5
N1'—C6'—H6'	107.7	C20—C19—C3	112.4 (2)
C7'—C6'—H6'	107.7	C20—C19—H19C	109.1
C5'—C6'—H6'	107.7	C3—C19—H19C	109.1
N1—C6—C7	113.76 (18)	C20—C19—H19D	109.1
N1—C6—C5	109.86 (19)	C3—C19—H19D	109.1
C7—C6—C5	108.67 (18)	H19C—C19—H19D	107.9
N1—C6—H6	108.1	C19—C20—H20A	109.5
C7—C6—H6	108.1	C19—C20—H20B	109.5
C5—C6—H6	108.1	H20A—C20—H20B	109.5
C12—C7—C8	117.5 (3)	C19—C20—H20C	109.5
C12—C7—C6	123.1 (2)	H20A—C20—H20C	109.5
C8—C7—C6	119.3 (2)	H20B—C20—H20C	109.5
C12'—C7'—C8'	118.1 (3)	C19'—C20'—H20D	109.5
C12'—C7'—C6'	122.8 (2)	C19'—C20'—H20E	109.5
C8'—C7'—C6'	119.1 (3)	H20D—C20'—H20E	109.5
C7—C8—C9	120.9 (3)	C19'—C20'—H20F	109.5
C7—C8—H8	119.6	H20D—C20'—H20F	109.5
C9—C8—H8	119.6	H20E—C20'—H20F	109.5
C9'—C8'—C7'	121.0 (4)	O2'—C21'—N1'	124.2 (3)
C9'—C8'—H8'	119.5	O2'—C21'—C22'	119.7 (2)
C7'—C8'—H8'	119.5	N1'—C21'—C22'	116.1 (2)
C10'—C9'—C8'	120.1 (4)	O2—C21—N1	124.3 (2)
C10'—C9'—H9'	119.9	O2—C21—C22	119.1 (2)
C8'—C9'—H9'	119.9	N1—C21—C22	116.5 (2)
C10—C9—C8	120.6 (3)	C21—C22—Cl1	110.20 (19)
C10—C9—H9	119.7	C21—C22—Cl2	106.73 (17)
C8—C9—H9	119.7	Cl1—C22—Cl2	111.37 (14)
C9'—C10'—C11'	120.1 (4)	C21—C22—H22	109.5
C9'—C10'—H10'	120.0	Cl1—C22—H22	109.5
C11'—C10'—H10'	120.0	Cl2—C22—H22	109.5
C11—C10—C9	118.9 (3)	C21'—C22'—Cl2'	110.0 (2)
C11—C10—H10	120.5	C21'—C22'—Cl1'	107.5 (2)
C9—C10—H10	120.5	Cl2'—C22'—Cl1'	110.59 (15)
C10—C11—C12	121.1 (3)	C21'—C22'—H22'	109.6
C10—C11—H11	119.5	Cl2'—C22'—H22'	109.6
C12—C11—H11	119.5	Cl1'—C22'—H22'	109.6
C10'—C11'—C12'	119.7 (4)	C21'—N1'—C6'	122.8 (2)
C10'—C11'—H11'	120.2	C21'—N1'—C2'	117.16 (19)
C12'—C11'—H11'	120.2	C6'—N1'—C2'	119.39 (19)
C7—C12—C11	120.9 (3)	C21—N1—C2	117.17 (18)
C7—C12—H12	119.5	C21—N1—C6	123.13 (19)
C11—C12—H12	119.5	C2—N1—C6	118.98 (17)
N1'—C2'—C3'—C4'	56.8 (3)	N1—C2—C13—C14	50.1 (3)
C13'—C2'—C3'—C4'	−70.3 (3)	C3—C2—C13—C14	176.8 (2)
N1'—C2'—C3'—C19'	−65.0 (3)	C18'—C13'—C14'—C15'	3.1 (4)
C13'—C2'—C3'—C19'	168.0 (2)	C2'—C13'—C14'—C15'	−175.8 (3)
N1—C2—C3—C4	59.4 (2)	C18—C13—C14—C15	2.3 (4)
C13—C2—C3—C4	−68.1 (3)	C2—C13—C14—C15	−179.5 (2)
N1—C2—C3—C19	−62.8 (2)	C13—C14—C15—C16	−1.0 (4)
C13—C2—C3—C19	169.7 (2)	C13'—C14'—C15'—C16'	−0.5 (5)
C2—C3—C4—O1	155.8 (2)	C14—C15—C16—C17	−1.4 (5)
C19—C3—C4—O1	−80.2 (3)	C14'—C15'—C16'—C17'	−1.9 (5)
C2—C3—C4—C5	−21.9 (3)	C15—C16—C17—C18	2.5 (5)
C19—C3—C4—C5	102.1 (2)	C15'—C16'—C17'—C18'	1.5 (5)
C2'—C3'—C4'—O1'	162.7 (3)	C16—C17—C18—C13	−1.1 (4)
C19'—C3'—C4'—O1'	−74.9 (3)	C14—C13—C18—C17	−1.3 (4)
C2'—C3'—C4'—C5'	−17.0 (3)	C2—C13—C18—C17	−179.5 (2)
C19'—C3'—C4'—C5'	105.4 (3)	C14'—C13'—C18'—C17'	−3.5 (4)
O1—C4—C5—C6	151.5 (2)	C2'—C13'—C18'—C17'	175.4 (3)
C3—C4—C5—C6	−30.8 (3)	C16'—C17'—C18'—C13'	1.2 (5)
O1'—C4'—C5'—C6'	147.2 (3)	C4'—C3'—C19'—C20'	69.2 (3)
C3'—C4'—C5'—C6'	−33.1 (3)	C2'—C3'—C19'—C20'	−167.4 (3)
C4'—C5'—C6'—N1'	40.9 (3)	C4—C3—C19—C20	73.3 (3)
C4'—C5'—C6'—C7'	166.8 (2)	C2—C3—C19—C20	−164.0 (2)
C4—C5—C6—N1	44.8 (3)	O2—C21—C22—Cl1	31.9 (3)
C4—C5—C6—C7	169.9 (2)	N1—C21—C22—Cl1	−150.47 (18)
N1—C6—C7—C12	42.3 (3)	O2—C21—C22—Cl2	−89.1 (3)
C5—C6—C7—C12	−80.4 (3)	N1—C21—C22—Cl2	88.5 (2)
N1—C6—C7—C8	−141.7 (2)	O2'—C21'—C22'—Cl2'	39.6 (3)
C5—C6—C7—C8	95.6 (3)	N1'—C21'—C22'—Cl2'	−142.5 (2)
N1'—C6'—C7'—C12'	43.1 (4)	O2'—C21'—C22'—Cl1'	−80.9 (3)
C5'—C6'—C7'—C12'	−81.3 (3)	N1'—C21'—C22'—Cl1'	97.0 (2)
N1'—C6'—C7'—C8'	−140.4 (2)	O2'—C21'—N1'—C6'	179.5 (3)
C5'—C6'—C7'—C8'	95.2 (3)	C22'—C21'—N1'—C6'	1.7 (4)
C12—C7—C8—C9	1.4 (4)	O2'—C21'—N1'—C2'	8.8 (4)
C6—C7—C8—C9	−174.8 (3)	C22'—C21'—N1'—C2'	−169.0 (2)
C12'—C7'—C8'—C9'	−0.1 (5)	C7'—C6'—N1'—C21'	68.2 (3)
C6'—C7'—C8'—C9'	−176.8 (3)	C5'—C6'—N1'—C21'	−168.6 (2)
C7'—C8'—C9'—C10'	0.0 (6)	C7'—C6'—N1'—C2'	−121.3 (2)
C7—C8—C9—C10	−0.5 (5)	C5'—C6'—N1'—C2'	1.9 (3)
C8'—C9'—C10'—C11'	−0.2 (6)	C13'—C2'—N1'—C21'	−107.6 (2)
C8—C9—C10—C11	−1.1 (5)	C3'—C2'—N1'—C21'	121.0 (2)
C9—C10—C11—C12	1.7 (6)	C13'—C2'—N1'—C6'	81.4 (3)
C9'—C10'—C11'—C12'	0.5 (6)	C3'—C2'—N1'—C6'	−50.1 (3)
C8—C7—C12—C11	−0.9 (5)	O2—C21—N1—C2	14.1 (3)
C6—C7—C12—C11	175.2 (3)	C22—C21—N1—C2	−163.3 (2)
C10—C11—C12—C7	−0.7 (5)	O2—C21—N1—C6	−175.7 (2)
C8'—C7'—C12'—C11'	0.4 (5)	C22—C21—N1—C6	6.8 (3)
C6'—C7'—C12'—C11'	177.0 (3)	C13—C2—N1—C21	−105.9 (2)
C10'—C11'—C12'—C7'	−0.6 (6)	C3—C2—N1—C21	124.3 (2)
N1'—C2'—C13'—C18'	−117.4 (3)	C13—C2—N1—C6	83.6 (2)
C3'—C2'—C13'—C18'	8.6 (4)	C3—C2—N1—C6	−46.2 (2)
N1'—C2'—C13'—C14'	61.4 (3)	C7—C6—N1—C21	63.0 (3)
C3'—C2'—C13'—C14'	−172.6 (2)	C5—C6—N1—C21	−175.0 (2)
N1—C2—C13—C18	−131.7 (2)	C7—C6—N1—C2	−127.1 (2)
C3—C2—C13—C18	−5.0 (3)	C5—C6—N1—C2	−5.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.98	2.49	3.435 (3)	161
C20′—H20F···O1ii	0.96	2.48	3.415 (4)	164
C6′—H6′···O2′iii	0.98	2.51	3.292 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.98	2.49	3.435 (3)	161
C20′—H20F⋯O1ii	0.96	2.48	3.415 (4)	164
C6′—H6′⋯O2′iii	0.98	2.51	3.292 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) .