(E)-1-(4-Chloro-phen-yl)-3-[4-(diethyl-amino)phen-yl]prop-2-en-1-one.

The asymmetric unit of the title chalcone derivative, C(19)H(20)ClNO, contains two independent mol-ecules, which differ in the conformations of the ethyl groups in the diethyl-amino substituents. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into ribbons propogating in [010]. The crystal packing also exhibits weak C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Fun et al. (2009 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Svetlichny et al. (2007 ▶); Xu et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C19H20ClNO

M = 313.81

Monoclinic,

a = 17.2073 (2) Å

b = 11.9467 (1) Å

c = 15.7996 (2) Å

β = 97.268 (1)°

V = 3221.84 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.33 × 0.23 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.925, T max = 0.977

47596 measured reflections

9400 independent reflections

6241 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.122

S = 1.10

9400 reflections

401 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054683/cv2675sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054683/cv2675Isup2.hkl

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

C19H20ClNO	F(000) = 1328
Mr = 313.81	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Melting point = 374–375 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.2073 (2) Å	Cell parameters from 9400 reflections
b = 11.9467 (1) Å	θ = 1.9–30.0°
c = 15.7996 (2) Å	µ = 0.24 mm−1
β = 97.268 (1)°	T = 100 K
V = 3221.84 (6) Å3	Block, yellow
Z = 8	0.33 × 0.23 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	9400 independent reflections
Radiation source: sealed tube	6241 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→24
Tmin = 0.925, Tmax = 0.977	k = −12→16
47596 measured reflections	l = −21→22

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.7024P] where P = (Fo2 + 2Fc2)/3
9400 reflections	(Δ/σ)max = 0.001
401 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1A	1.33545 (2)	0.22869 (4)	0.37652 (3)	0.02632 (11)
O1A	1.00783 (6)	−0.07143 (9)	0.29241 (7)	0.0250 (3)
N1A	0.62274 (7)	0.22634 (11)	−0.01499 (8)	0.0220 (3)
C1A	1.11964 (9)	0.17759 (13)	0.25803 (10)	0.0203 (3)
H1AA	1.0859	0.2119	0.2151	0.024*
C2A	1.19351 (9)	0.22284 (13)	0.28205 (10)	0.0209 (3)
H2AA	1.2099	0.2857	0.2544	0.025*
C3A	1.24235 (9)	0.17306 (13)	0.34767 (10)	0.0193 (3)
C4A	1.21866 (9)	0.07958 (13)	0.38999 (10)	0.0216 (3)
H4AA	1.2513	0.0484	0.4353	0.026*
C5A	1.14600 (9)	0.03364 (13)	0.36369 (10)	0.0208 (3)
H5AA	1.1305	−0.0304	0.3906	0.025*
C6A	1.09523 (9)	0.08156 (13)	0.29733 (10)	0.0186 (3)
C7A	1.01754 (9)	0.02632 (13)	0.27110 (10)	0.0185 (3)
C8A	0.95504 (9)	0.09153 (13)	0.22182 (10)	0.0197 (3)
H8AA	0.9640	0.1659	0.2086	0.024*
C9A	0.88478 (9)	0.04481 (13)	0.19551 (9)	0.0193 (3)
H9AA	0.8786	−0.0291	0.2118	0.023*
C10A	0.81767 (9)	0.09526 (13)	0.14509 (10)	0.0190 (3)
C11A	0.81717 (9)	0.20500 (13)	0.11330 (10)	0.0208 (3)
H11A	0.8611	0.2498	0.1272	0.025*
C12A	0.75375 (9)	0.24823 (13)	0.06228 (10)	0.0215 (4)
H12A	0.7560	0.3214	0.0427	0.026*
C13A	0.68503 (9)	0.18439 (13)	0.03865 (10)	0.0194 (3)
C14A	0.68454 (9)	0.07499 (13)	0.07266 (10)	0.0220 (4)
H14A	0.6400	0.0308	0.0606	0.026*
C15A	0.74903 (9)	0.03261 (13)	0.12349 (10)	0.0207 (3)
H15A	0.7469	−0.0401	0.1441	0.025*
C16A	0.62152 (9)	0.34250 (13)	−0.04343 (10)	0.0236 (4)
H16A	0.5841	0.3495	−0.0945	0.028*
H16B	0.6728	0.3615	−0.0586	0.028*
C17A	0.60016 (10)	0.42641 (14)	0.02253 (11)	0.0268 (4)
H17A	0.6049	0.5011	0.0013	0.040*
H17B	0.6349	0.4173	0.0746	0.040*
H17C	0.5472	0.4137	0.0333	0.040*
C18A	0.55139 (9)	0.16108 (14)	−0.03719 (10)	0.0231 (4)
H18A	0.5658	0.0839	−0.0462	0.028*
H18B	0.5244	0.1890	−0.0906	0.028*
C19A	0.49514 (10)	0.16418 (15)	0.02990 (11)	0.0290 (4)
H19A	0.4499	0.1194	0.0112	0.043*
H19B	0.4792	0.2400	0.0380	0.043*
H19C	0.5209	0.1351	0.0828	0.043*
Cl1B	0.16956 (2)	0.81186 (4)	0.18284 (3)	0.03390 (13)
O1B	0.51160 (6)	1.07982 (9)	0.24066 (8)	0.0283 (3)
N1B	0.90996 (7)	0.73741 (11)	0.47926 (8)	0.0193 (3)
C1B	0.40036 (9)	0.82319 (13)	0.25395 (10)	0.0209 (3)
H1BA	0.4401	0.7729	0.2726	0.025*
C2B	0.32374 (9)	0.78546 (14)	0.23590 (10)	0.0227 (4)
H2BA	0.3121	0.7102	0.2425	0.027*
C3B	0.26505 (9)	0.86039 (14)	0.20805 (10)	0.0221 (4)
C4B	0.28072 (9)	0.97338 (14)	0.19930 (10)	0.0250 (4)
H4BA	0.2405	1.0234	0.1816	0.030*
C5B	0.35717 (9)	1.01030 (13)	0.21739 (10)	0.0217 (3)
H5BA	0.3682	1.0859	0.2115	0.026*
C6B	0.41803 (9)	0.93639 (13)	0.24428 (9)	0.0176 (3)
C7B	0.49926 (9)	0.98249 (13)	0.26100 (10)	0.0189 (3)
C8B	0.56250 (9)	0.91209 (13)	0.30276 (10)	0.0207 (3)
H8BA	0.5512	0.8404	0.3206	0.025*
C9B	0.63645 (9)	0.94976 (13)	0.31555 (9)	0.0187 (3)
H9BA	0.6447	1.0201	0.2932	0.022*
C10B	0.70517 (9)	0.89533 (13)	0.35960 (10)	0.0180 (3)
C11B	0.70277 (9)	0.79079 (13)	0.39960 (10)	0.0200 (3)
H11B	0.6547	0.7551	0.3992	0.024*
C12B	0.76888 (9)	0.73904 (13)	0.43942 (10)	0.0196 (3)
H12B	0.7645	0.6699	0.4655	0.023*
C13B	0.84368 (9)	0.78947 (13)	0.44136 (9)	0.0173 (3)
C14B	0.84647 (9)	0.89580 (13)	0.40271 (10)	0.0186 (3)
H14B	0.8943	0.9322	0.4034	0.022*
C15B	0.77899 (9)	0.94644 (13)	0.36396 (10)	0.0189 (3)
H15B	0.7826	1.0170	0.3399	0.023*
C16B	0.98874 (9)	0.77527 (13)	0.46801 (10)	0.0198 (3)
H16C	0.9861	0.8185	0.4157	0.024*
H16D	1.0215	0.7104	0.4619	0.024*
C17B	1.02667 (9)	0.84630 (14)	0.54171 (11)	0.0251 (4)
H17D	1.0795	0.8637	0.5329	0.038*
H17E	1.0269	0.8056	0.5941	0.038*
H17F	0.9975	0.9144	0.5446	0.038*
C18B	0.90602 (9)	0.63347 (13)	0.52717 (10)	0.0209 (3)
H18C	0.8606	0.6359	0.5578	0.025*
H18D	0.9523	0.6276	0.5689	0.025*
C19B	0.90064 (10)	0.53012 (14)	0.47043 (11)	0.0259 (4)
H19D	0.9030	0.4641	0.5053	0.039*
H19E	0.9435	0.5298	0.4370	0.039*
H19F	0.8520	0.5312	0.4332	0.039*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0194 (2)	0.0273 (2)	0.0314 (2)	−0.00409 (16)	−0.00011 (16)	0.00009 (18)
O1A	0.0213 (6)	0.0216 (6)	0.0316 (7)	−0.0014 (5)	0.0018 (5)	0.0073 (5)
N1A	0.0195 (7)	0.0215 (7)	0.0240 (7)	0.0001 (6)	−0.0012 (6)	0.0034 (6)
C1A	0.0200 (8)	0.0212 (9)	0.0196 (8)	0.0020 (7)	0.0013 (6)	0.0031 (7)
C2A	0.0223 (8)	0.0182 (8)	0.0228 (8)	−0.0009 (7)	0.0049 (7)	0.0011 (7)
C3A	0.0166 (7)	0.0190 (9)	0.0221 (8)	−0.0004 (6)	0.0016 (6)	−0.0023 (7)
C4A	0.0209 (8)	0.0204 (9)	0.0227 (8)	0.0043 (7)	−0.0001 (7)	0.0013 (7)
C5A	0.0219 (8)	0.0165 (8)	0.0241 (8)	0.0017 (6)	0.0039 (7)	0.0035 (7)
C6A	0.0198 (8)	0.0173 (8)	0.0192 (8)	0.0016 (6)	0.0040 (6)	0.0000 (6)
C7A	0.0189 (8)	0.0200 (9)	0.0173 (8)	0.0004 (6)	0.0048 (6)	0.0003 (6)
C8A	0.0205 (8)	0.0175 (8)	0.0214 (8)	0.0006 (6)	0.0035 (6)	0.0017 (6)
C9A	0.0218 (8)	0.0185 (8)	0.0185 (8)	0.0012 (6)	0.0053 (6)	0.0000 (6)
C10A	0.0193 (8)	0.0185 (9)	0.0193 (8)	0.0009 (6)	0.0033 (6)	−0.0008 (6)
C11A	0.0171 (8)	0.0203 (9)	0.0251 (8)	−0.0018 (6)	0.0034 (6)	−0.0019 (7)
C12A	0.0213 (8)	0.0166 (9)	0.0271 (9)	0.0009 (6)	0.0054 (7)	0.0030 (7)
C13A	0.0194 (8)	0.0199 (9)	0.0191 (8)	0.0008 (6)	0.0031 (6)	−0.0003 (6)
C14A	0.0205 (8)	0.0188 (9)	0.0258 (9)	−0.0027 (7)	0.0003 (7)	−0.0009 (7)
C15A	0.0229 (8)	0.0154 (8)	0.0231 (8)	−0.0007 (6)	0.0010 (7)	0.0007 (6)
C16A	0.0236 (8)	0.0234 (9)	0.0230 (8)	0.0002 (7)	−0.0007 (7)	0.0072 (7)
C17A	0.0237 (9)	0.0243 (10)	0.0328 (10)	−0.0003 (7)	0.0046 (7)	0.0045 (7)
C18A	0.0226 (8)	0.0231 (9)	0.0219 (8)	−0.0012 (7)	−0.0039 (7)	−0.0011 (7)
C19A	0.0265 (9)	0.0285 (10)	0.0317 (10)	−0.0065 (8)	0.0029 (8)	−0.0009 (8)
Cl1B	0.0241 (2)	0.0341 (3)	0.0408 (3)	−0.00895 (18)	−0.00643 (19)	0.0077 (2)
O1B	0.0260 (6)	0.0199 (7)	0.0384 (7)	−0.0013 (5)	0.0015 (5)	0.0073 (5)
N1B	0.0173 (7)	0.0173 (7)	0.0232 (7)	−0.0002 (5)	0.0016 (5)	0.0041 (5)
C1B	0.0232 (8)	0.0174 (9)	0.0222 (8)	0.0044 (7)	0.0032 (7)	0.0003 (7)
C2B	0.0281 (9)	0.0155 (8)	0.0243 (8)	−0.0030 (7)	0.0022 (7)	−0.0006 (7)
C3B	0.0204 (8)	0.0231 (9)	0.0222 (8)	−0.0033 (7)	0.0002 (7)	0.0008 (7)
C4B	0.0239 (9)	0.0219 (9)	0.0281 (9)	0.0042 (7)	−0.0014 (7)	0.0018 (7)
C5B	0.0251 (9)	0.0147 (8)	0.0247 (9)	−0.0005 (7)	0.0005 (7)	0.0000 (7)
C6B	0.0207 (8)	0.0170 (8)	0.0153 (7)	0.0013 (6)	0.0027 (6)	−0.0012 (6)
C7B	0.0213 (8)	0.0178 (9)	0.0178 (8)	0.0004 (6)	0.0029 (6)	0.0002 (6)
C8B	0.0226 (8)	0.0164 (8)	0.0229 (8)	0.0008 (6)	0.0025 (7)	0.0029 (7)
C9B	0.0217 (8)	0.0160 (8)	0.0191 (8)	0.0017 (6)	0.0049 (6)	−0.0015 (6)
C10B	0.0189 (8)	0.0163 (8)	0.0194 (8)	0.0014 (6)	0.0050 (6)	−0.0017 (6)
C11B	0.0170 (8)	0.0198 (9)	0.0242 (8)	−0.0012 (6)	0.0063 (6)	−0.0025 (7)
C12B	0.0215 (8)	0.0151 (8)	0.0225 (8)	−0.0005 (6)	0.0045 (6)	0.0006 (6)
C13B	0.0188 (8)	0.0166 (8)	0.0166 (7)	0.0004 (6)	0.0028 (6)	−0.0021 (6)
C14B	0.0176 (8)	0.0174 (8)	0.0209 (8)	−0.0032 (6)	0.0030 (6)	−0.0024 (6)
C15B	0.0229 (8)	0.0143 (8)	0.0202 (8)	0.0008 (6)	0.0054 (6)	−0.0011 (6)
C16B	0.0172 (8)	0.0197 (8)	0.0229 (8)	0.0010 (6)	0.0036 (6)	0.0013 (7)
C17B	0.0201 (8)	0.0257 (9)	0.0288 (9)	−0.0012 (7)	0.0002 (7)	−0.0004 (7)
C18B	0.0199 (8)	0.0207 (9)	0.0218 (8)	0.0003 (7)	0.0010 (6)	0.0041 (7)
C19B	0.0254 (9)	0.0198 (9)	0.0314 (9)	0.0011 (7)	−0.0007 (7)	0.0020 (7)

Cl1A—C3A	1.7411 (15)	Cl1B—C3B	1.7405 (16)
O1A—C7A	1.2326 (18)	O1B—C7B	1.2320 (18)
N1A—C13A	1.3741 (19)	N1B—C13B	1.3687 (19)
N1A—C16A	1.458 (2)	N1B—C18B	1.460 (2)
N1A—C18A	1.459 (2)	N1B—C16B	1.4610 (19)
C1A—C2A	1.389 (2)	C1B—C2B	1.388 (2)
C1A—C6A	1.394 (2)	C1B—C6B	1.399 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.384 (2)	C2B—C3B	1.379 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.389 (2)	C3B—C4B	1.387 (2)
C4A—C5A	1.381 (2)	C4B—C5B	1.383 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.399 (2)	C5B—C6B	1.394 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.501 (2)	C6B—C7B	1.495 (2)
C7A—C8A	1.469 (2)	C7B—C8B	1.465 (2)
C8A—C9A	1.349 (2)	C8B—C9B	1.341 (2)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.449 (2)	C9B—C10B	1.448 (2)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C15A	1.404 (2)	C10B—C11B	1.403 (2)
C10A—C11A	1.404 (2)	C10B—C15B	1.403 (2)
C11A—C12A	1.373 (2)	C11B—C12B	1.375 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.417 (2)	C12B—C13B	1.418 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.414 (2)	C13B—C14B	1.413 (2)
C14A—C15A	1.381 (2)	C14B—C15B	1.382 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.524 (2)	C16B—C17B	1.520 (2)
C16A—H16A	0.9700	C16B—H16C	0.9700
C16A—H16B	0.9700	C16B—H16D	0.9700
C17A—H17A	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17C	0.9600	C17B—H17F	0.9600
C18A—C19A	1.524 (2)	C18B—C19B	1.522 (2)
C18A—H18A	0.9700	C18B—H18C	0.9700
C18A—H18B	0.9700	C18B—H18D	0.9700
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C13A—N1A—C16A	121.13 (13)	C13B—N1B—C18B	121.49 (12)
C13A—N1A—C18A	121.34 (13)	C13B—N1B—C16B	122.73 (13)
C16A—N1A—C18A	117.10 (12)	C18B—N1B—C16B	115.52 (12)
C2A—C1A—C6A	121.02 (14)	C2B—C1B—C6B	120.35 (14)
C2A—C1A—H1AA	119.5	C2B—C1B—H1BA	119.8
C6A—C1A—H1AA	119.5	C6B—C1B—H1BA	119.8
C3A—C2A—C1A	119.04 (15)	C3B—C2B—C1B	119.53 (15)
C3A—C2A—H2AA	120.5	C3B—C2B—H2BA	120.2
C1A—C2A—H2AA	120.5	C1B—C2B—H2BA	120.2
C2A—C3A—C4A	121.26 (14)	C2B—C3B—C4B	121.31 (15)
C2A—C3A—Cl1A	118.93 (12)	C2B—C3B—Cl1B	119.26 (13)
C4A—C3A—Cl1A	119.81 (12)	C4B—C3B—Cl1B	119.42 (12)
C5A—C4A—C3A	118.98 (15)	C5B—C4B—C3B	118.81 (15)
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.6
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.6
C4A—C5A—C6A	121.24 (15)	C4B—C5B—C6B	121.27 (15)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.4
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.4
C1A—C6A—C5A	118.40 (14)	C5B—C6B—C1B	118.71 (14)
C1A—C6A—C7A	123.13 (14)	C5B—C6B—C7B	118.04 (14)
C5A—C6A—C7A	118.47 (14)	C1B—C6B—C7B	123.26 (14)
O1A—C7A—C8A	122.12 (14)	O1B—C7B—C8B	121.12 (14)
O1A—C7A—C6A	119.20 (14)	O1B—C7B—C6B	119.33 (14)
C8A—C7A—C6A	118.68 (14)	C8B—C7B—C6B	119.54 (14)
C9A—C8A—C7A	120.77 (15)	C9B—C8B—C7B	120.80 (15)
C9A—C8A—H8AA	119.6	C9B—C8B—H8BA	119.6
C7A—C8A—H8AA	119.6	C7B—C8B—H8BA	119.6
C8A—C9A—C10A	128.20 (15)	C8B—C9B—C10B	128.56 (15)
C8A—C9A—H9AA	115.9	C8B—C9B—H9BA	115.7
C10A—C9A—H9AA	115.9	C10B—C9B—H9BA	115.7
C15A—C10A—C11A	116.37 (14)	C11B—C10B—C15B	116.32 (14)
C15A—C10A—C9A	119.98 (14)	C11B—C10B—C9B	123.19 (14)
C11A—C10A—C9A	123.63 (14)	C15B—C10B—C9B	120.48 (14)
C12A—C11A—C10A	122.00 (14)	C12B—C11B—C10B	122.45 (14)
C12A—C11A—H11A	119.0	C12B—C11B—H11B	118.8
C10A—C11A—H11A	119.0	C10B—C11B—H11B	118.8
C11A—C12A—C13A	121.81 (15)	C11B—C12B—C13B	121.00 (14)
C11A—C12A—H12A	119.1	C11B—C12B—H12B	119.5
C13A—C12A—H12A	119.1	C13B—C12B—H12B	119.5
N1A—C13A—C14A	122.01 (14)	N1B—C13B—C14B	121.71 (14)
N1A—C13A—C12A	121.73 (14)	N1B—C13B—C12B	121.35 (14)
C14A—C13A—C12A	116.25 (14)	C14B—C13B—C12B	116.93 (14)
C15A—C14A—C13A	121.14 (14)	C15B—C14B—C13B	120.84 (14)
C15A—C14A—H14A	119.4	C15B—C14B—H14B	119.6
C13A—C14A—H14A	119.4	C13B—C14B—H14B	119.6
C14A—C15A—C10A	122.38 (15)	C14B—C15B—C10B	122.41 (14)
C14A—C15A—H15A	118.8	C14B—C15B—H15B	118.8
C10A—C15A—H15A	118.8	C10B—C15B—H15B	118.8
N1A—C16A—C17A	114.24 (13)	N1B—C16B—C17B	113.25 (13)
N1A—C16A—H16A	108.7	N1B—C16B—H16C	108.9
C17A—C16A—H16A	108.7	C17B—C16B—H16C	108.9
N1A—C16A—H16B	108.7	N1B—C16B—H16D	108.9
C17A—C16A—H16B	108.7	C17B—C16B—H16D	108.9
H16A—C16A—H16B	107.6	H16C—C16B—H16D	107.7
C16A—C17A—H17A	109.5	C16B—C17B—H17D	109.5
C16A—C17A—H17B	109.5	C16B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C16A—C17A—H17C	109.5	C16B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
N1A—C18A—C19A	114.14 (13)	N1B—C18B—C19B	112.83 (13)
N1A—C18A—H18A	108.7	N1B—C18B—H18C	109.0
C19A—C18A—H18A	108.7	C19B—C18B—H18C	109.0
N1A—C18A—H18B	108.7	N1B—C18B—H18D	109.0
C19A—C18A—H18B	108.7	C19B—C18B—H18D	109.0
H18A—C18A—H18B	107.6	H18C—C18B—H18D	107.8
C18A—C19A—H19A	109.5	C18B—C19B—H19D	109.5
C18A—C19A—H19B	109.5	C18B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C18A—C19A—H19C	109.5	C18B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C6A—C1A—C2A—C3A	−1.8 (2)	C6B—C1B—C2B—C3B	0.2 (2)
C1A—C2A—C3A—C4A	−0.4 (2)	C1B—C2B—C3B—C4B	−1.3 (2)
C1A—C2A—C3A—Cl1A	179.03 (12)	C1B—C2B—C3B—Cl1B	178.31 (12)
C2A—C3A—C4A—C5A	2.3 (2)	C2B—C3B—C4B—C5B	1.3 (2)
Cl1A—C3A—C4A—C5A	−177.11 (12)	Cl1B—C3B—C4B—C5B	−178.31 (12)
C3A—C4A—C5A—C6A	−2.0 (2)	C3B—C4B—C5B—C6B	−0.2 (2)
C2A—C1A—C6A—C5A	2.1 (2)	C4B—C5B—C6B—C1B	−0.9 (2)
C2A—C1A—C6A—C7A	−177.12 (14)	C4B—C5B—C6B—C7B	178.88 (14)
C4A—C5A—C6A—C1A	−0.1 (2)	C2B—C1B—C6B—C5B	0.9 (2)
C4A—C5A—C6A—C7A	179.12 (14)	C2B—C1B—C6B—C7B	−178.86 (14)
C1A—C6A—C7A—O1A	161.56 (15)	C5B—C6B—C7B—O1B	−9.0 (2)
C5A—C6A—C7A—O1A	−17.6 (2)	C1B—C6B—C7B—O1B	170.70 (15)
C1A—C6A—C7A—C8A	−19.4 (2)	C5B—C6B—C7B—C8B	169.77 (14)
C5A—C6A—C7A—C8A	161.42 (14)	C1B—C6B—C7B—C8B	−10.5 (2)
O1A—C7A—C8A—C9A	−2.2 (2)	O1B—C7B—C8B—C9B	−3.8 (2)
C6A—C7A—C8A—C9A	178.77 (14)	C6B—C7B—C8B—C9B	177.38 (14)
C7A—C8A—C9A—C10A	−178.39 (14)	C7B—C8B—C9B—C10B	176.11 (14)
C8A—C9A—C10A—C15A	179.71 (15)	C8B—C9B—C10B—C11B	−2.2 (3)
C8A—C9A—C10A—C11A	1.6 (3)	C8B—C9B—C10B—C15B	177.64 (15)
C15A—C10A—C11A—C12A	−1.4 (2)	C15B—C10B—C11B—C12B	−1.5 (2)
C9A—C10A—C11A—C12A	176.80 (15)	C9B—C10B—C11B—C12B	178.41 (14)
C10A—C11A—C12A—C13A	−0.1 (2)	C10B—C11B—C12B—C13B	−0.4 (2)
C16A—N1A—C13A—C14A	174.59 (14)	C18B—N1B—C13B—C14B	173.21 (14)
C18A—N1A—C13A—C14A	2.3 (2)	C16B—N1B—C13B—C14B	−12.8 (2)
C16A—N1A—C13A—C12A	−6.0 (2)	C18B—N1B—C13B—C12B	−6.6 (2)
C18A—N1A—C13A—C12A	−178.37 (14)	C16B—N1B—C13B—C12B	167.43 (14)
C11A—C12A—C13A—N1A	−177.54 (14)	C11B—C12B—C13B—N1B	−178.57 (14)
C11A—C12A—C13A—C14A	1.9 (2)	C11B—C12B—C13B—C14B	1.6 (2)
N1A—C13A—C14A—C15A	177.16 (15)	N1B—C13B—C14B—C15B	179.29 (14)
C12A—C13A—C14A—C15A	−2.2 (2)	C12B—C13B—C14B—C15B	−0.9 (2)
C13A—C14A—C15A—C10A	0.8 (2)	C13B—C14B—C15B—C10B	−1.0 (2)
C11A—C10A—C15A—C14A	1.0 (2)	C11B—C10B—C15B—C14B	2.2 (2)
C9A—C10A—C15A—C14A	−177.26 (14)	C9B—C10B—C15B—C14B	−177.68 (14)
C13A—N1A—C16A—C17A	−78.38 (18)	C13B—N1B—C16B—C17B	99.04 (17)
C18A—N1A—C16A—C17A	94.27 (16)	C18B—N1B—C16B—C17B	−86.63 (16)
C13A—N1A—C18A—C19A	81.27 (18)	C13B—N1B—C18B—C19B	84.38 (17)
C16A—N1A—C18A—C19A	−91.36 (17)	C16B—N1B—C18B—C19B	−90.03 (16)

Cg1 is the centroid of the C10B–C15B ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1BA···O1Bi	0.93	2.47	3.2746 (19)	145
C16B—H16C···O1Aii	0.97	2.42	3.3749 (19)	168
C2A—H2AA···Cg1iii	0.93	2.60	3.3377 (17)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10B–C15B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1B—H1BA⋯O1Bi	0.93	2.47	3.2746 (19)	145
C16B—H16C⋯O1Aii	0.97	2.42	3.3749 (19)	168
C2A—H2AA⋯Cg1iii	0.93	2.60	3.3377 (17)	137

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