(Z)-3β-(2-Chloro-anilino)-17(20)-pregnene.

In the pregnene fragment of the title compound, C27H38ClN, the three six-membered rings exhibit chair conformations and the five-membered ring has a distorted envelope form with the fused C atom not bearing a methyl group as the flap atom. The amino group is involved in the formation of an intra-molecular N-H⋯Cl hydrogen bond. The crystal packing exhibits no short inter-molecular contacts.

Related literature

For applications of pregnene-type steroidal alkaloid derivatives, see: Hua et al. (2005 ▶); Hunter & Priest (2006 ▶). For the crystal structure of the related compound (Z)-3α-(1,3-dioxoisoindolin-2-yl)-17 (20)-pregnene, see: Qi et al. (2011 ▶).

Experimental

Crystal data

C27H38ClN

M = 412.03

Monoclinic,

a = 7.281 (1) Å

b = 17.467 (2) Å

c = 9.1310 (12) Å

β = 106.447 (7)°

V = 1113.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 113 K

0.26 × 0.24 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.953, T max = 0.967

14303 measured reflections

5276 independent reflections

4089 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.066

S = 0.97

5276 reflections

269 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 2537 Friedel pairs

Flack parameter: 0.02 (3)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007290/cv5384sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007290/cv5384Isup2.hkl

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

C27H38ClN	F(000) = 448
Mr = 412.03	Dx = 1.229 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4165 reflections
a = 7.281 (1) Å	θ = 1.2–27.9°
b = 17.467 (2) Å	µ = 0.19 mm−1
c = 9.1310 (12) Å	T = 113 K
β = 106.447 (7)°	Prism, colourless
V = 1113.7 (2) Å3	0.26 × 0.24 × 0.18 mm
Z = 2

Rigaku Saturn724 CCD diffractometer	5276 independent reflections
Radiation source: rotating anode	4089 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.038
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −22→22
Tmin = 0.953, Tmax = 0.967	l = −11→11
14303 measured reflections

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0299P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
5276 reflections	Δρmax = 0.18 e Å−3
269 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 2537 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (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
Cl1	0.65026 (5)	0.47549 (2)	0.27405 (4)	0.02681 (9)
N1	0.72923 (18)	0.63876 (7)	0.23132 (14)	0.0219 (3)
C1	0.4738 (2)	0.83125 (8)	0.15203 (16)	0.0184 (3)
H1A	0.3408	0.8434	0.1515	0.022*
H1B	0.4885	0.8457	0.0511	0.022*
C1'	0.86537 (19)	0.59002 (8)	0.20670 (15)	0.0179 (3)
C2	0.50533 (19)	0.74475 (8)	0.17404 (17)	0.0193 (3)
H2A	0.4214	0.7179	0.0843	0.023*
H2B	0.4669	0.7286	0.2650	0.023*
C2'	0.84853 (19)	0.51050 (8)	0.22294 (15)	0.0188 (3)
C3	0.7134 (2)	0.72010 (8)	0.19420 (16)	0.0194 (3)
H3	0.7421	0.7272	0.0943	0.023*
C3'	0.9773 (2)	0.45928 (8)	0.19481 (17)	0.0235 (3)
H3'	0.9593	0.4060	0.2064	0.028*
C4	0.8522 (2)	0.76977 (8)	0.31296 (16)	0.0193 (3)
H4A	0.8370	0.7586	0.4152	0.023*
H4B	0.9852	0.7567	0.3149	0.023*
C4'	1.1333 (2)	0.48461 (9)	0.14969 (15)	0.0260 (3)
H4'	1.2228	0.4493	0.1302	0.031*
C5	0.81801 (19)	0.85484 (8)	0.27867 (16)	0.0168 (3)
H5	0.8293	0.8631	0.1732	0.020*
C5'	1.1556 (2)	0.56290 (9)	0.13369 (16)	0.0253 (3)
H5'	1.2617	0.5813	0.1029	0.030*
C6	0.97282 (19)	0.90405 (8)	0.38521 (17)	0.0213 (3)
H6A	0.9690	0.8966	0.4918	0.026*
H6B	1.1002	0.8874	0.3786	0.026*
C6'	1.0254 (2)	0.61462 (8)	0.16199 (16)	0.0218 (3)
H6'	1.0446	0.6679	0.1510	0.026*
C7	0.94543 (18)	0.98860 (8)	0.34445 (16)	0.0203 (3)
H7A	0.9652	0.9971	0.2428	0.024*
H7B	1.0425	1.0189	0.4200	0.024*
C8	0.74540 (18)	1.01621 (7)	0.34212 (16)	0.0156 (3)
H8	0.7312	1.0116	0.4476	0.019*
C9	0.58989 (18)	0.96592 (8)	0.23272 (15)	0.0147 (3)
H9	0.6120	0.9703	0.1298	0.018*
C10	0.61220 (18)	0.87966 (8)	0.27571 (15)	0.0151 (3)
C11	0.38697 (19)	0.99738 (7)	0.21507 (16)	0.0197 (3)
H11A	0.2953	0.9688	0.1323	0.024*
H11B	0.3527	0.9875	0.3108	0.024*
C12	0.36389 (19)	1.08327 (8)	0.17908 (17)	0.0192 (3)
H12A	0.3758	1.0925	0.0752	0.023*
H12B	0.2344	1.0998	0.1805	0.023*
C13	0.51445 (19)	1.13112 (7)	0.29440 (15)	0.0151 (3)
C14	0.71243 (18)	1.09903 (8)	0.29169 (16)	0.0157 (3)
H14	0.7130	1.1001	0.1823	0.019*
C15	0.85384 (19)	1.16029 (8)	0.37215 (16)	0.0213 (3)
H15A	0.9781	1.1549	0.3491	0.026*
H15B	0.8754	1.1586	0.4841	0.026*
C16	0.7503 (2)	1.23417 (8)	0.30321 (18)	0.0241 (3)
H16A	0.7832	1.2766	0.3780	0.029*
H16B	0.7870	1.2491	0.2107	0.029*
C17	0.5354 (2)	1.21616 (8)	0.26260 (15)	0.0171 (3)
C18	0.4833 (2)	1.12587 (8)	0.45464 (16)	0.0217 (3)
H18A	0.5895	1.1512	0.5293	0.026*
H18B	0.4779	1.0720	0.4829	0.026*
H18C	0.3626	1.1511	0.4534	0.026*
C19	0.57245 (19)	0.86552 (8)	0.43077 (15)	0.0199 (3)
H19A	0.5888	0.8110	0.4565	0.024*
H19B	0.4410	0.8810	0.4242	0.024*
H19C	0.6623	0.8956	0.5101	0.024*
C20	0.4035 (2)	1.27000 (8)	0.22004 (15)	0.0198 (3)
H20	0.4507	1.3198	0.2092	0.024*
C21	0.18870 (19)	1.26393 (8)	0.18609 (17)	0.0228 (3)
H21A	0.1510	1.2099	0.1759	0.027*
H21B	0.1274	1.2909	0.0906	0.027*
H21C	0.1483	1.2871	0.2697	0.027*
H10	0.635 (3)	0.6182 (12)	0.259 (2)	0.059 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02351 (18)	0.01886 (16)	0.0400 (2)	−0.00103 (17)	0.01213 (15)	−0.00106 (17)
N1	0.0254 (7)	0.0144 (6)	0.0291 (7)	0.0032 (5)	0.0132 (6)	0.0030 (5)
C1	0.0165 (7)	0.0165 (7)	0.0206 (8)	0.0016 (6)	0.0030 (6)	0.0003 (6)
C1'	0.0200 (7)	0.0189 (7)	0.0130 (7)	0.0026 (6)	0.0020 (5)	−0.0013 (6)
C2	0.0190 (7)	0.0168 (7)	0.0206 (8)	0.0010 (6)	0.0032 (6)	0.0004 (6)
C2'	0.0175 (7)	0.0200 (7)	0.0180 (7)	−0.0008 (6)	0.0037 (6)	−0.0003 (6)
C3	0.0234 (7)	0.0140 (7)	0.0211 (8)	0.0022 (6)	0.0070 (6)	0.0027 (6)
C3'	0.0263 (8)	0.0176 (8)	0.0239 (8)	0.0050 (6)	0.0026 (6)	−0.0016 (6)
C4	0.0181 (7)	0.0168 (7)	0.0235 (8)	0.0047 (6)	0.0066 (6)	0.0019 (6)
C4'	0.0240 (7)	0.0274 (9)	0.0268 (8)	0.0092 (7)	0.0076 (6)	−0.0013 (7)
C5	0.0152 (7)	0.0182 (7)	0.0176 (7)	0.0025 (5)	0.0056 (6)	0.0010 (6)
C5'	0.0223 (8)	0.0320 (9)	0.0232 (8)	0.0016 (6)	0.0088 (6)	−0.0020 (6)
C6	0.0131 (7)	0.0214 (8)	0.0277 (8)	0.0029 (6)	0.0030 (6)	0.0004 (6)
C6'	0.0240 (8)	0.0175 (8)	0.0241 (8)	0.0002 (6)	0.0069 (6)	0.0015 (6)
C7	0.0130 (6)	0.0196 (9)	0.0265 (8)	0.0002 (5)	0.0029 (6)	0.0003 (6)
C8	0.0129 (7)	0.0156 (7)	0.0177 (7)	0.0003 (5)	0.0033 (5)	−0.0009 (5)
C9	0.0141 (6)	0.0152 (7)	0.0146 (7)	0.0014 (6)	0.0039 (5)	0.0003 (5)
C10	0.0123 (6)	0.0161 (7)	0.0165 (7)	0.0007 (5)	0.0033 (5)	0.0006 (6)
C11	0.0136 (7)	0.0165 (8)	0.0260 (8)	−0.0003 (5)	0.0008 (6)	−0.0006 (6)
C12	0.0140 (7)	0.0159 (7)	0.0253 (8)	0.0012 (5)	0.0018 (6)	−0.0010 (6)
C13	0.0147 (7)	0.0144 (7)	0.0159 (7)	0.0009 (5)	0.0039 (5)	0.0009 (5)
C14	0.0139 (7)	0.0186 (7)	0.0154 (7)	−0.0006 (6)	0.0054 (5)	0.0014 (5)
C15	0.0150 (7)	0.0203 (8)	0.0282 (8)	−0.0018 (6)	0.0052 (6)	−0.0004 (6)
C16	0.0188 (8)	0.0202 (8)	0.0313 (9)	−0.0017 (6)	0.0036 (6)	0.0007 (6)
C17	0.0198 (7)	0.0168 (7)	0.0143 (7)	−0.0019 (6)	0.0043 (6)	−0.0032 (6)
C18	0.0231 (7)	0.0209 (7)	0.0239 (8)	0.0033 (6)	0.0114 (6)	0.0004 (6)
C19	0.0187 (7)	0.0203 (7)	0.0222 (8)	0.0029 (6)	0.0081 (6)	0.0022 (6)
C20	0.0236 (7)	0.0164 (7)	0.0207 (7)	−0.0002 (6)	0.0083 (6)	−0.0006 (6)
C21	0.0249 (8)	0.0184 (8)	0.0266 (8)	0.0032 (6)	0.0099 (6)	−0.0002 (6)

Cl1—C2'	1.7485 (14)	C8—C9	1.5527 (18)
N1—C1'	1.3726 (18)	C8—H8	1.0000
N1—C3	1.4576 (17)	C9—C11	1.5414 (17)
N1—H10	0.875 (19)	C9—C10	1.554 (2)
C1—C2	1.5329 (18)	C9—H9	1.0000
C1—C10	1.5367 (18)	C10—C19	1.5432 (18)
C1—H1A	0.9900	C11—C12	1.5349 (18)
C1—H1B	0.9900	C11—H11A	0.9900
C1'—C2'	1.4060 (19)	C11—H11B	0.9900
C1'—C6'	1.4064 (19)	C12—C13	1.5347 (19)
C2—C3	1.5350 (18)	C12—H12A	0.9900
C2—H2A	0.9900	C12—H12B	0.9900
C2—H2B	0.9900	C13—C17	1.5295 (19)
C2'—C3'	1.3715 (18)	C13—C18	1.5456 (18)
C3—C4	1.5263 (19)	C13—C14	1.5533 (18)
C3—H3	1.0000	C14—C15	1.5219 (19)
C3'—C4'	1.386 (2)	C14—H14	1.0000
C3'—H3'	0.9500	C15—C16	1.537 (2)
C4—C5	1.5244 (19)	C15—H15A	0.9900
C4—H4A	0.9900	C15—H15B	0.9900
C4—H4B	0.9900	C16—C17	1.5355 (19)
C4'—C5'	1.390 (2)	C16—H16A	0.9900
C4'—H4'	0.9500	C16—H16B	0.9900
C5—C6	1.5280 (19)	C17—C20	1.3215 (19)
C5—C10	1.5528 (18)	C18—H18A	0.9800
C5—H5	1.0000	C18—H18B	0.9800
C5'—C6'	1.386 (2)	C18—H18C	0.9800
C5'—H5'	0.9500	C19—H19A	0.9800
C6—C7	1.5222 (19)	C19—H19B	0.9800
C6—H6A	0.9900	C19—H19C	0.9800
C6—H6B	0.9900	C20—C21	1.5092 (19)
C6'—H6'	0.9500	C20—H20	0.9500
C7—C8	1.5286 (18)	C21—H21A	0.9800
C7—H7A	0.9900	C21—H21B	0.9800
C7—H7B	0.9900	C21—H21C	0.9800
C8—C14	1.5166 (18)
C1'—N1—C3	125.43 (13)	C8—C9—C10	112.39 (10)
C1'—N1—H10	117.1 (14)	C11—C9—H9	106.2
C3—N1—H10	116.8 (14)	C8—C9—H9	106.2
C2—C1—C10	113.79 (11)	C10—C9—H9	106.2
C2—C1—H1A	108.8	C1—C10—C19	109.39 (11)
C10—C1—H1A	108.8	C1—C10—C5	106.74 (11)
C2—C1—H1B	108.8	C19—C10—C5	111.72 (10)
C10—C1—H1B	108.8	C1—C10—C9	110.37 (10)
H1A—C1—H1B	107.7	C19—C10—C9	110.70 (11)
N1—C1'—C2'	120.46 (13)	C5—C10—C9	107.84 (10)
N1—C1'—C6'	123.65 (13)	C12—C11—C9	114.48 (11)
C2'—C1'—C6'	115.88 (12)	C12—C11—H11A	108.6
C1—C2—C3	113.46 (11)	C9—C11—H11A	108.6
C1—C2—H2A	108.9	C12—C11—H11B	108.6
C3—C2—H2A	108.9	C9—C11—H11B	108.6
C1—C2—H2B	108.9	H11A—C11—H11B	107.6
C3—C2—H2B	108.9	C13—C12—C11	111.82 (11)
H2A—C2—H2B	107.7	C13—C12—H12A	109.3
C3'—C2'—C1'	122.68 (13)	C11—C12—H12A	109.3
C3'—C2'—Cl1	118.79 (11)	C13—C12—H12B	109.3
C1'—C2'—Cl1	118.48 (10)	C11—C12—H12B	109.3
N1—C3—C4	113.32 (11)	H12A—C12—H12B	107.9
N1—C3—C2	108.16 (11)	C17—C13—C12	119.26 (12)
C4—C3—C2	111.01 (11)	C17—C13—C18	106.65 (11)
N1—C3—H3	108.1	C12—C13—C18	110.45 (12)
C4—C3—H3	108.1	C17—C13—C14	101.81 (11)
C2—C3—H3	108.1	C12—C13—C14	106.17 (11)
C2'—C3'—C4'	120.58 (13)	C18—C13—C14	112.30 (11)
C2'—C3'—H3'	119.7	C8—C14—C15	119.79 (11)
C4'—C3'—H3'	119.7	C8—C14—C13	114.02 (11)
C5—C4—C3	111.79 (11)	C15—C14—C13	104.05 (11)
C5—C4—H4A	109.3	C8—C14—H14	106.0
C3—C4—H4A	109.3	C15—C14—H14	106.0
C5—C4—H4B	109.3	C13—C14—H14	106.0
C3—C4—H4B	109.3	C14—C15—C16	101.91 (11)
H4A—C4—H4B	107.9	C14—C15—H15A	111.4
C3'—C4'—C5'	118.37 (14)	C16—C15—H15A	111.4
C3'—C4'—H4'	120.8	C14—C15—H15B	111.4
C5'—C4'—H4'	120.8	C16—C15—H15B	111.4
C4—C5—C6	111.68 (11)	H15A—C15—H15B	109.3
C4—C5—C10	112.12 (11)	C17—C16—C15	105.97 (11)
C6—C5—C10	112.85 (11)	C17—C16—H16A	110.5
C4—C5—H5	106.6	C15—C16—H16A	110.5
C6—C5—H5	106.6	C17—C16—H16B	110.5
C10—C5—H5	106.6	C15—C16—H16B	110.5
C6'—C5'—C4'	121.03 (14)	H16A—C16—H16B	108.7
C6'—C5'—H5'	119.5	C20—C17—C13	130.08 (13)
C4'—C5'—H5'	119.5	C20—C17—C16	122.11 (13)
C7—C6—C5	111.61 (11)	C13—C17—C16	107.61 (11)
C7—C6—H6A	109.3	C13—C18—H18A	109.5
C5—C6—H6A	109.3	C13—C18—H18B	109.5
C7—C6—H6B	109.3	H18A—C18—H18B	109.5
C5—C6—H6B	109.3	C13—C18—H18C	109.5
H6A—C6—H6B	108.0	H18A—C18—H18C	109.5
C5'—C6'—C1'	121.45 (14)	H18B—C18—H18C	109.5
C5'—C6'—H6'	119.3	C10—C19—H19A	109.5
C1'—C6'—H6'	119.3	C10—C19—H19B	109.5
C6—C7—C8	111.58 (11)	H19A—C19—H19B	109.5
C6—C7—H7A	109.3	C10—C19—H19C	109.5
C8—C7—H7A	109.3	H19A—C19—H19C	109.5
C6—C7—H7B	109.3	H19B—C19—H19C	109.5
C8—C7—H7B	109.3	C17—C20—C21	129.41 (13)
H7A—C7—H7B	108.0	C17—C20—H20	115.3
C14—C8—C7	111.92 (11)	C21—C20—H20	115.3
C14—C8—C9	108.69 (11)	C20—C21—H21A	109.5
C7—C8—C9	110.42 (11)	C20—C21—H21B	109.5
C14—C8—H8	108.6	H21A—C21—H21B	109.5
C7—C8—H8	108.6	C20—C21—H21C	109.5
C9—C8—H8	108.6	H21A—C21—H21C	109.5
C11—C9—C8	111.62 (11)	H21B—C21—H21C	109.5
C11—C9—C10	113.61 (10)
C3—N1—C1'—C2'	−169.28 (13)	C4—C5—C10—C9	−177.45 (11)
C3—N1—C1'—C6'	9.5 (2)	C6—C5—C10—C9	55.39 (14)
C10—C1—C2—C3	−52.24 (16)	C11—C9—C10—C1	59.98 (14)
N1—C1'—C2'—C3'	177.82 (13)	C8—C9—C10—C1	−172.07 (10)
C6'—C1'—C2'—C3'	−1.1 (2)	C11—C9—C10—C19	−61.28 (13)
N1—C1'—C2'—Cl1	0.32 (18)	C8—C9—C10—C19	66.67 (13)
C6'—C1'—C2'—Cl1	−178.57 (10)	C11—C9—C10—C5	176.22 (11)
C1'—N1—C3—C4	−80.43 (17)	C8—C9—C10—C5	−55.83 (13)
C1'—N1—C3—C2	156.05 (13)	C8—C9—C11—C12	49.27 (15)
C1—C2—C3—N1	173.59 (11)	C10—C9—C11—C12	177.62 (11)
C1—C2—C3—C4	48.69 (16)	C9—C11—C12—C13	−52.96 (16)
C1'—C2'—C3'—C4'	0.6 (2)	C11—C12—C13—C17	170.00 (11)
Cl1—C2'—C3'—C4'	178.12 (11)	C11—C12—C13—C18	−65.98 (15)
N1—C3—C4—C5	−174.30 (11)	C11—C12—C13—C14	56.00 (15)
C2—C3—C4—C5	−52.36 (16)	C7—C8—C14—C15	−53.21 (16)
C2'—C3'—C4'—C5'	−0.1 (2)	C9—C8—C14—C15	−175.43 (11)
C3—C4—C5—C6	−172.62 (11)	C7—C8—C14—C13	−177.36 (11)
C3—C4—C5—C10	59.60 (15)	C9—C8—C14—C13	60.42 (14)
C3'—C4'—C5'—C6'	0.0 (2)	C17—C13—C14—C8	171.90 (11)
C4—C5—C6—C7	176.45 (11)	C12—C13—C14—C8	−62.61 (14)
C10—C5—C6—C7	−56.16 (15)	C18—C13—C14—C8	58.19 (15)
C4'—C5'—C6'—C1'	−0.5 (2)	C17—C13—C14—C15	39.67 (13)
N1—C1'—C6'—C5'	−177.85 (13)	C12—C13—C14—C15	165.16 (11)
C2'—C1'—C6'—C5'	1.0 (2)	C18—C13—C14—C15	−74.04 (14)
C5—C6—C7—C8	55.07 (16)	C8—C14—C15—C16	−171.63 (12)
C6—C7—C8—C14	−176.32 (11)	C13—C14—C15—C16	−42.82 (13)
C6—C7—C8—C9	−55.10 (15)	C14—C15—C16—C17	29.17 (15)
C14—C8—C9—C11	−50.99 (14)	C12—C13—C17—C20	47.9 (2)
C7—C8—C9—C11	−174.11 (11)	C18—C13—C17—C20	−77.94 (18)
C14—C8—C9—C10	−179.98 (10)	C14—C13—C17—C20	164.22 (14)
C7—C8—C9—C10	56.89 (14)	C12—C13—C17—C16	−137.25 (13)
C2—C1—C10—C19	−65.95 (15)	C18—C13—C17—C16	96.90 (13)
C2—C1—C10—C5	55.09 (14)	C14—C13—C17—C16	−20.94 (14)
C2—C1—C10—C9	172.02 (11)	C15—C16—C17—C20	170.51 (13)
C4—C5—C10—C1	−58.86 (13)	C15—C16—C17—C13	−4.83 (16)
C6—C5—C10—C1	173.99 (11)	C13—C17—C20—C21	−1.4 (2)
C4—C5—C10—C19	60.68 (15)	C16—C17—C20—C21	−175.62 (14)
C6—C5—C10—C19	−66.48 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···Cl1	0.875 (19)	2.50 (2)	2.9569 (13)	113.5 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H10⋯Cl1	0.875 (19)	2.50 (2)	2.9569 (13)	113.5 (16)