1-Benzyl-3,5-bis-(4-chloro-benzyl-idene)piperidin-4-one.

The title compound, C(26)H(21)Cl(2)NO, crystallizes with two symmetry-independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the central heterocyclic ring adopts a sofa conformation. The dihedral angles between the planar part of this central heterocyclic ring [maximum deviations of 0.011 (1) and 0.036 (1) Å in mol-ecules A and B, respectively] and the two almost planar [maximum deviations of 0.020 (1) and 0.008 (1) Å in A and 0.007 (1) and 0.011 (1) in B] side-chain fragments that include the aromatic ring and bridging atoms are 20.1 (1) and 31.2 (1)° in mol-ecule A, and 26.4 (1) and 19.6 (1)° in mol-ecule B. The dihedral angles between the planar part of the heterocyclic ring and the benzyl substituent are 79.7 (1) and 53.2 (1)° in mol-ecules A and B, respectively. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the two independent mol-ecules into dimers.

Related literature

For non-linear optical organic compounds with two-photon absorption properties and potential biophotonic materials, see: Nesterov et al. (2003 ▶, 2007 ▶); Sarkisov et al. (2005 ▶). For the biological importance of 4-piperidone, see: Jia et al. (1988 ▶); Dimmock et al. (2001 ▶). For the synthesis of the title compound, see: Dimmock et al. (2001 ▶). For related structures, see: Nesterov et al. (2003 ▶, 2007 ▶, 2011 ▶). For details concerning weak hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For van der Waals radii, see: Rowland & Taylor (1996 ▶).

Experimental

Crystal data

C26H21Cl2NO

M = 434.34

Triclinic,

a = 12.504 (2) Å

b = 13.414 (4) Å

c = 14.763 (2) Å

α = 102.736 (3)°

β = 111.676 (2)°

γ = 104.066 (3)°

V = 2095.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.25 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.922, T max = 0.962

24542 measured reflections

8251 independent reflections

7049 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.02

8251 reflections

541 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018587/fl2348sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018587/fl2348Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018587/fl2348Isup3.cml

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

C26H21Cl2NO	Z = 4
Mr = 434.34	F(000) = 904
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.504 (2) Å	Cell parameters from 2357 reflections
b = 13.414 (4) Å	θ = 2.4–25.4°
c = 14.763 (2) Å	µ = 0.33 mm−1
α = 102.736 (3)°	T = 100 K
β = 111.676 (2)°	Plate, yellow
γ = 104.066 (3)°	0.25 × 0.20 × 0.12 mm
V = 2095.7 (8) Å3

Bruker SMART APEXII CCD diffractometer	8251 independent reflections
Radiation source: fine-focus sealed tube	7049 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.922, Tmax = 0.962	k = −16→16
24542 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.057P)2 + 1.110P] where P = (Fo2 + 2Fc2)/3
8251 reflections	(Δ/σ)max = 0.001
541 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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	0.01606 (5)	0.78507 (4)	0.69670 (4)	0.03870 (13)
Cl2A	0.65255 (5)	0.12893 (5)	0.08931 (4)	0.03854 (13)
O1A	0.35806 (13)	0.34345 (11)	0.51320 (10)	0.0336 (3)
N1A	0.24037 (13)	0.45157 (12)	0.27541 (11)	0.0214 (3)
C1A	0.20424 (16)	0.49694 (15)	0.19088 (13)	0.0235 (4)
H1AA	0.2213	0.4597	0.1348	0.028*
H1AB	0.2548	0.5758	0.2178	0.028*
C2A	0.24894 (16)	0.52293 (14)	0.37107 (13)	0.0225 (4)
H2AA	0.1714	0.5376	0.3558	0.027*
H2AB	0.3172	0.5937	0.3974	0.027*
C3A	0.27142 (16)	0.46956 (14)	0.45281 (13)	0.0225 (4)
C4A	0.33892 (16)	0.39154 (14)	0.44991 (13)	0.0237 (4)
C5A	0.38468 (15)	0.37528 (14)	0.36967 (13)	0.0226 (4)
C6A	0.35812 (16)	0.43693 (15)	0.29532 (13)	0.0230 (4)
H6AA	0.4249	0.5093	0.3251	0.028*
H6AB	0.3550	0.3959	0.2293	0.028*
C7A	0.23584 (16)	0.48474 (15)	0.52962 (13)	0.0243 (4)
H7AA	0.2517	0.4389	0.5698	0.029*
C8A	0.17781 (16)	0.55822 (15)	0.56197 (13)	0.0242 (4)
C9A	0.12682 (16)	0.53599 (16)	0.62905 (13)	0.0273 (4)
H9AA	0.1272	0.4722	0.6470	0.033*
C10A	0.07631 (16)	0.60382 (16)	0.66965 (14)	0.0279 (4)
H10A	0.0426	0.5874	0.7150	0.033*
C11A	0.07585 (17)	0.69624 (16)	0.64286 (14)	0.0283 (4)
C12A	0.12458 (17)	0.72161 (15)	0.57642 (14)	0.0287 (4)
H12A	0.1224	0.7849	0.5581	0.034*
C13A	0.17646 (17)	0.65334 (15)	0.53720 (13)	0.0265 (4)
H13A	0.2115	0.6712	0.4931	0.032*
C14A	0.44035 (15)	0.30143 (15)	0.36640 (13)	0.0238 (4)
H14A	0.4473	0.2674	0.4173	0.029*
C15A	0.49216 (15)	0.26528 (15)	0.29595 (13)	0.0235 (4)
C16A	0.49531 (16)	0.15947 (15)	0.27926 (14)	0.0256 (4)
H16A	0.4647	0.1160	0.3133	0.031*
C17A	0.54175 (17)	0.11651 (16)	0.21450 (15)	0.0285 (4)
H17A	0.5406	0.0436	0.2023	0.034*
C18A	0.59003 (16)	0.18160 (16)	0.16772 (14)	0.0271 (4)
C19A	0.59069 (16)	0.28780 (15)	0.18407 (14)	0.0269 (4)
H19A	0.6250	0.3321	0.1524	0.032*
C20A	0.54096 (16)	0.32860 (15)	0.24702 (13)	0.0250 (4)
H20A	0.5399	0.4007	0.2572	0.030*
C21A	0.06923 (16)	0.48300 (14)	0.14668 (12)	0.0212 (3)
C22A	0.03196 (17)	0.57277 (14)	0.14847 (14)	0.0265 (4)
H22A	0.0921	0.6446	0.1806	0.032*
C23A	−0.09251 (18)	0.55824 (15)	0.10361 (14)	0.0300 (4)
H23A	−0.1169	0.6201	0.1046	0.036*
C24A	−0.18115 (17)	0.45380 (15)	0.05750 (14)	0.0275 (4)
H24A	−0.2662	0.4438	0.0266	0.033*
C25A	−0.14470 (17)	0.36398 (15)	0.05688 (13)	0.0257 (4)
H25A	−0.2051	0.2923	0.0263	0.031*
C26A	−0.02083 (17)	0.37834 (14)	0.10062 (13)	0.0240 (4)
H26A	0.0032	0.3163	0.0993	0.029*
Cl1B	0.95734 (5)	−0.23822 (4)	0.32282 (4)	0.03777 (13)
Cl2B	0.37099 (5)	0.37742 (4)	0.99889 (4)	0.03390 (13)
O1B	0.56754 (19)	0.16150 (17)	0.50449 (12)	0.0619 (6)
N1B	0.80808 (13)	0.13829 (11)	0.75624 (11)	0.0214 (3)
C1B	0.90276 (16)	0.13447 (14)	0.85070 (13)	0.0231 (4)
H1BA	0.9251	0.2006	0.9096	0.028*
H1BB	0.9775	0.1383	0.8406	0.028*
C2B	0.77495 (16)	0.04704 (14)	0.66319 (13)	0.0218 (3)
H2BA	0.7250	−0.0217	0.6647	0.026*
H2BB	0.8506	0.0382	0.6615	0.026*
C3B	0.70258 (17)	0.06941 (14)	0.56795 (13)	0.0244 (4)
C4B	0.62426 (19)	0.13581 (17)	0.57702 (15)	0.0321 (4)
C5B	0.61373 (16)	0.16622 (14)	0.67621 (13)	0.0236 (4)
C6B	0.69847 (16)	0.14481 (14)	0.76757 (13)	0.0221 (4)
H6BA	0.7233	0.2045	0.8326	0.026*
H6BB	0.6544	0.0753	0.7718	0.026*
C7B	0.70371 (17)	0.03605 (15)	0.47530 (14)	0.0259 (4)
H7BA	0.6560	0.0600	0.4238	0.031*
C8B	0.76759 (16)	−0.03161 (14)	0.44228 (13)	0.0242 (4)
C9B	0.79157 (17)	−0.02325 (15)	0.35788 (14)	0.0260 (4)
H9BA	0.7661	0.0258	0.3247	0.031*
C10B	0.85128 (18)	−0.08460 (15)	0.32190 (14)	0.0288 (4)
H10B	0.8684	−0.0767	0.2658	0.035*
C11B	0.88558 (17)	−0.15780 (15)	0.36921 (14)	0.0274 (4)
C12B	0.86061 (17)	−0.17053 (15)	0.45097 (14)	0.0273 (4)
H12B	0.8835	−0.2218	0.4820	0.033*
C13B	0.80220 (17)	−0.10792 (14)	0.48681 (13)	0.0254 (4)
H13B	0.7851	−0.1167	0.5427	0.030*
C14B	0.52956 (16)	0.21299 (14)	0.67633 (13)	0.0241 (4)
H14B	0.4869	0.2238	0.6133	0.029*
C15B	0.49337 (15)	0.24968 (14)	0.75771 (13)	0.0216 (3)
C16B	0.43215 (16)	0.32462 (14)	0.74851 (14)	0.0235 (4)
H16B	0.4161	0.3487	0.6906	0.028*
C17B	0.39458 (16)	0.36416 (15)	0.82178 (14)	0.0256 (4)
H17B	0.3554	0.4164	0.8154	0.031*
C18B	0.41504 (16)	0.32627 (15)	0.90467 (13)	0.0235 (4)
C19B	0.47058 (16)	0.24907 (15)	0.91413 (13)	0.0245 (4)
H19B	0.4811	0.2217	0.9697	0.029*
C20B	0.51062 (16)	0.21212 (14)	0.84192 (13)	0.0234 (4)
H20B	0.5505	0.1604	0.8494	0.028*
C21B	0.86682 (15)	0.03449 (14)	0.88084 (13)	0.0223 (4)
C22B	0.88113 (16)	−0.06166 (15)	0.83723 (14)	0.0265 (4)
H22B	0.9155	−0.0639	0.7895	0.032*
C23B	0.84610 (18)	−0.15432 (16)	0.86226 (15)	0.0324 (4)
H23B	0.8552	−0.2196	0.8310	0.039*
C24B	0.79766 (18)	−0.15083 (17)	0.93324 (16)	0.0360 (5)
H24B	0.7741	−0.2137	0.9511	0.043*
C25B	0.78367 (18)	−0.05629 (18)	0.97777 (16)	0.0344 (4)
H25B	0.7504	−0.0542	1.0262	0.041*
C26B	0.81808 (17)	0.03602 (16)	0.95213 (14)	0.0278 (4)
H26B	0.8083	0.1009	0.9835	0.033*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0431 (3)	0.0438 (3)	0.0363 (3)	0.0205 (2)	0.0243 (2)	0.0098 (2)
Cl2A	0.0449 (3)	0.0511 (3)	0.0420 (3)	0.0289 (2)	0.0311 (2)	0.0227 (2)
O1A	0.0478 (8)	0.0417 (8)	0.0285 (7)	0.0268 (7)	0.0218 (6)	0.0227 (6)
N1A	0.0245 (7)	0.0260 (7)	0.0169 (7)	0.0114 (6)	0.0089 (6)	0.0108 (6)
C1A	0.0262 (9)	0.0290 (9)	0.0191 (8)	0.0118 (7)	0.0101 (7)	0.0129 (7)
C2A	0.0246 (9)	0.0240 (9)	0.0195 (8)	0.0090 (7)	0.0095 (7)	0.0084 (7)
C3A	0.0226 (8)	0.0219 (8)	0.0186 (8)	0.0054 (7)	0.0065 (7)	0.0066 (7)
C4A	0.0256 (9)	0.0253 (9)	0.0179 (8)	0.0078 (7)	0.0075 (7)	0.0085 (7)
C5A	0.0211 (8)	0.0254 (9)	0.0200 (8)	0.0080 (7)	0.0071 (7)	0.0095 (7)
C6A	0.0223 (8)	0.0289 (9)	0.0208 (8)	0.0099 (7)	0.0100 (7)	0.0124 (7)
C7A	0.0236 (9)	0.0270 (9)	0.0193 (8)	0.0068 (7)	0.0072 (7)	0.0095 (7)
C8A	0.0219 (8)	0.0273 (9)	0.0158 (8)	0.0050 (7)	0.0053 (7)	0.0031 (7)
C9A	0.0249 (9)	0.0310 (10)	0.0195 (8)	0.0045 (8)	0.0065 (7)	0.0088 (7)
C10A	0.0244 (9)	0.0356 (10)	0.0201 (9)	0.0066 (8)	0.0101 (7)	0.0075 (8)
C11A	0.0246 (9)	0.0324 (10)	0.0224 (9)	0.0081 (8)	0.0100 (7)	0.0023 (8)
C12A	0.0305 (10)	0.0265 (9)	0.0254 (9)	0.0076 (8)	0.0114 (8)	0.0070 (7)
C13A	0.0298 (9)	0.0279 (9)	0.0198 (8)	0.0064 (8)	0.0119 (7)	0.0073 (7)
C14A	0.0211 (8)	0.0292 (9)	0.0213 (8)	0.0077 (7)	0.0086 (7)	0.0122 (7)
C15A	0.0183 (8)	0.0300 (9)	0.0204 (8)	0.0097 (7)	0.0051 (7)	0.0105 (7)
C16A	0.0241 (9)	0.0319 (10)	0.0244 (9)	0.0119 (8)	0.0111 (7)	0.0135 (8)
C17A	0.0298 (10)	0.0304 (10)	0.0312 (10)	0.0148 (8)	0.0152 (8)	0.0139 (8)
C18A	0.0219 (9)	0.0399 (11)	0.0249 (9)	0.0153 (8)	0.0122 (7)	0.0134 (8)
C19A	0.0208 (9)	0.0337 (10)	0.0263 (9)	0.0081 (7)	0.0086 (7)	0.0159 (8)
C20A	0.0209 (8)	0.0280 (9)	0.0227 (9)	0.0081 (7)	0.0060 (7)	0.0099 (7)
C21A	0.0271 (9)	0.0259 (9)	0.0132 (7)	0.0113 (7)	0.0091 (7)	0.0090 (7)
C22A	0.0307 (10)	0.0207 (9)	0.0252 (9)	0.0081 (7)	0.0094 (8)	0.0091 (7)
C23A	0.0363 (10)	0.0264 (9)	0.0298 (10)	0.0183 (8)	0.0128 (8)	0.0097 (8)
C24A	0.0260 (9)	0.0333 (10)	0.0245 (9)	0.0141 (8)	0.0106 (7)	0.0098 (8)
C25A	0.0289 (9)	0.0238 (9)	0.0211 (9)	0.0072 (7)	0.0098 (7)	0.0066 (7)
C26A	0.0333 (10)	0.0214 (8)	0.0192 (8)	0.0134 (7)	0.0111 (7)	0.0075 (7)
Cl1B	0.0470 (3)	0.0375 (3)	0.0438 (3)	0.0213 (2)	0.0317 (2)	0.0141 (2)
Cl2B	0.0409 (3)	0.0470 (3)	0.0327 (3)	0.0277 (2)	0.0248 (2)	0.0200 (2)
O1B	0.0977 (14)	0.1087 (15)	0.0391 (9)	0.0861 (13)	0.0465 (10)	0.0507 (10)
N1B	0.0246 (7)	0.0225 (7)	0.0189 (7)	0.0097 (6)	0.0109 (6)	0.0070 (6)
C1B	0.0229 (8)	0.0234 (9)	0.0210 (8)	0.0080 (7)	0.0089 (7)	0.0060 (7)
C2B	0.0238 (8)	0.0214 (8)	0.0206 (8)	0.0084 (7)	0.0106 (7)	0.0065 (7)
C3B	0.0293 (9)	0.0253 (9)	0.0224 (9)	0.0111 (7)	0.0129 (7)	0.0111 (7)
C4B	0.0419 (11)	0.0417 (11)	0.0281 (10)	0.0248 (9)	0.0209 (9)	0.0197 (9)
C5B	0.0280 (9)	0.0244 (9)	0.0221 (9)	0.0104 (7)	0.0128 (7)	0.0105 (7)
C6B	0.0265 (9)	0.0239 (9)	0.0202 (8)	0.0114 (7)	0.0126 (7)	0.0091 (7)
C7B	0.0285 (9)	0.0281 (9)	0.0231 (9)	0.0107 (8)	0.0119 (8)	0.0109 (7)
C8B	0.0250 (9)	0.0241 (9)	0.0195 (8)	0.0061 (7)	0.0095 (7)	0.0046 (7)
C9B	0.0311 (10)	0.0251 (9)	0.0222 (9)	0.0086 (8)	0.0131 (8)	0.0086 (7)
C10B	0.0338 (10)	0.0287 (9)	0.0246 (9)	0.0062 (8)	0.0178 (8)	0.0075 (8)
C11B	0.0272 (9)	0.0255 (9)	0.0284 (9)	0.0074 (7)	0.0155 (8)	0.0040 (7)
C12B	0.0306 (10)	0.0246 (9)	0.0245 (9)	0.0086 (8)	0.0119 (8)	0.0066 (7)
C13B	0.0297 (9)	0.0259 (9)	0.0197 (8)	0.0076 (7)	0.0125 (7)	0.0065 (7)
C14B	0.0276 (9)	0.0263 (9)	0.0212 (8)	0.0108 (7)	0.0107 (7)	0.0120 (7)
C15B	0.0186 (8)	0.0230 (8)	0.0210 (8)	0.0056 (7)	0.0073 (7)	0.0084 (7)
C16B	0.0227 (8)	0.0288 (9)	0.0240 (9)	0.0103 (7)	0.0113 (7)	0.0154 (7)
C17B	0.0237 (9)	0.0288 (9)	0.0303 (9)	0.0145 (7)	0.0126 (8)	0.0143 (8)
C18B	0.0223 (8)	0.0284 (9)	0.0230 (9)	0.0101 (7)	0.0126 (7)	0.0091 (7)
C19B	0.0271 (9)	0.0292 (9)	0.0214 (9)	0.0121 (8)	0.0113 (7)	0.0130 (7)
C20B	0.0262 (9)	0.0245 (9)	0.0229 (9)	0.0122 (7)	0.0110 (7)	0.0110 (7)
C21B	0.0183 (8)	0.0251 (9)	0.0200 (8)	0.0084 (7)	0.0049 (7)	0.0071 (7)
C22B	0.0255 (9)	0.0302 (10)	0.0243 (9)	0.0142 (8)	0.0091 (7)	0.0095 (8)
C23B	0.0295 (10)	0.0264 (10)	0.0329 (10)	0.0136 (8)	0.0035 (8)	0.0093 (8)
C24B	0.0273 (10)	0.0338 (11)	0.0412 (12)	0.0067 (8)	0.0061 (9)	0.0235 (9)
C25B	0.0297 (10)	0.0465 (12)	0.0328 (10)	0.0136 (9)	0.0154 (9)	0.0212 (9)
C26B	0.0283 (9)	0.0334 (10)	0.0253 (9)	0.0148 (8)	0.0122 (8)	0.0119 (8)

Cl1A—C11A	1.7507 (19)	Cl1B—C11B	1.7427 (19)
Cl2A—C18A	1.7398 (18)	Cl2B—C18B	1.7430 (18)
O1A—C4A	1.234 (2)	O1B—C4B	1.220 (2)
N1A—C6A	1.462 (2)	N1B—C6B	1.461 (2)
N1A—C2A	1.471 (2)	N1B—C2B	1.466 (2)
N1A—C1A	1.478 (2)	N1B—C1B	1.480 (2)
C1A—C21A	1.513 (2)	C1B—C21B	1.522 (2)
C1A—H1AA	0.9900	C1B—H1BA	0.9900
C1A—H1AB	0.9900	C1B—H1BB	0.9900
C2A—C3A	1.509 (2)	C2B—C3B	1.505 (2)
C2A—H2AA	0.9900	C2B—H2BA	0.9900
C2A—H2AB	0.9900	C2B—H2BB	0.9900
C3A—C7A	1.357 (2)	C3B—C7B	1.349 (2)
C3A—C4A	1.499 (2)	C3B—C4B	1.496 (3)
C4A—O1A	1.234 (2)	C4B—O1B	1.220 (2)
C4A—C5A	1.492 (2)	C4B—C5B	1.494 (2)
C5A—C14A	1.344 (3)	C5B—C14B	1.350 (2)
C5A—C6A	1.505 (2)	C5B—C6B	1.512 (2)
C6A—H6AA	0.9900	C6B—H6BA	0.9900
C6A—H6AB	0.9900	C6B—H6BB	0.9900
C7A—C8A	1.457 (3)	C7B—C8B	1.464 (3)
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C13A	1.405 (3)	C8B—C13B	1.403 (3)
C8A—C9A	1.407 (3)	C8B—C9B	1.406 (2)
C9A—C10A	1.380 (3)	C9B—C10B	1.384 (3)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.382 (3)	C10B—C11B	1.386 (3)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.392 (3)	C11B—C12B	1.388 (3)
C12A—C13A	1.388 (3)	C12B—C13B	1.381 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.471 (2)	C14B—C15B	1.463 (2)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.399 (3)	C15B—C16B	1.404 (2)
C15A—C20A	1.400 (3)	C15B—C20B	1.406 (2)
C16A—C17A	1.383 (3)	C16B—C17B	1.384 (2)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.386 (3)	C17B—C18B	1.388 (2)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.389 (3)	C18B—C19B	1.384 (3)
C19A—C20A	1.385 (3)	C19B—C20B	1.384 (2)
C19A—H19A	0.9500	C19B—H19B	0.9500
C20A—H20A	0.9500	C20B—H20B	0.9500
C21A—C22A	1.391 (2)	C21B—C22B	1.393 (3)
C21A—C26A	1.395 (2)	C21B—C26B	1.396 (2)
C22A—C23A	1.390 (3)	C22B—C23B	1.390 (3)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—C24A	1.386 (3)	C23B—C24B	1.389 (3)
C23A—H23A	0.9500	C23B—H23B	0.9500
C24A—C25A	1.387 (3)	C24B—C25B	1.377 (3)
C24A—H24A	0.9500	C24B—H24B	0.9500
C25A—C26A	1.384 (3)	C25B—C26B	1.389 (3)
C25A—H25A	0.9500	C25B—H25B	0.9500
C26A—H26A	0.9500	C26B—H26B	0.9500
C6A—N1A—C2A	109.92 (13)	C6B—N1B—C2B	110.96 (13)
C6A—N1A—C1A	110.49 (13)	C6B—N1B—C1B	112.52 (13)
C2A—N1A—C1A	111.03 (13)	C2B—N1B—C1B	112.25 (13)
N1A—C1A—C21A	112.10 (14)	N1B—C1B—C21B	116.12 (14)
N1A—C1A—H1AA	109.2	N1B—C1B—H1BA	108.3
C21A—C1A—H1AA	109.2	C21B—C1B—H1BA	108.3
N1A—C1A—H1AB	109.2	N1B—C1B—H1BB	108.3
C21A—C1A—H1AB	109.2	C21B—C1B—H1BB	108.3
H1AA—C1A—H1AB	107.9	H1BA—C1B—H1BB	107.4
N1A—C2A—C3A	110.47 (14)	N1B—C2B—C3B	109.53 (14)
N1A—C2A—H2AA	109.6	N1B—C2B—H2BA	109.8
C3A—C2A—H2AA	109.6	C3B—C2B—H2BA	109.8
N1A—C2A—H2AB	109.6	N1B—C2B—H2BB	109.8
C3A—C2A—H2AB	109.6	C3B—C2B—H2BB	109.8
H2AA—C2A—H2AB	108.1	H2BA—C2B—H2BB	108.2
C7A—C3A—C4A	115.94 (16)	C7B—C3B—C4B	117.08 (16)
C7A—C3A—C2A	126.30 (16)	C7B—C3B—C2B	125.51 (16)
C4A—C3A—C2A	117.76 (15)	C4B—C3B—C2B	117.40 (15)
O1A—C4A—C5A	120.82 (16)	O1B—C4B—C5B	120.89 (18)
O1A—C4A—C5A	120.82 (16)	O1B—C4B—C5B	120.89 (18)
O1A—C4A—C3A	120.99 (16)	O1B—C4B—C3B	121.05 (17)
O1A—C4A—C3A	120.99 (16)	O1B—C4B—C3B	121.05 (17)
C5A—C4A—C3A	118.17 (15)	C5B—C4B—C3B	118.02 (16)
C14A—C5A—C4A	116.67 (16)	C14B—C5B—C4B	116.11 (16)
C14A—C5A—C6A	125.41 (16)	C14B—C5B—C6B	125.67 (16)
C4A—C5A—C6A	117.80 (15)	C4B—C5B—C6B	118.20 (15)
N1A—C6A—C5A	110.04 (14)	N1B—C6B—C5B	110.34 (14)
N1A—C6A—H6AA	109.7	N1B—C6B—H6BA	109.6
C5A—C6A—H6AA	109.7	C5B—C6B—H6BA	109.6
N1A—C6A—H6AB	109.7	N1B—C6B—H6BB	109.6
C5A—C6A—H6AB	109.7	C5B—C6B—H6BB	109.6
H6AA—C6A—H6AB	108.2	H6BA—C6B—H6BB	108.1
C3A—C7A—C8A	131.99 (17)	C3B—C7B—C8B	129.59 (17)
C3A—C7A—H7AA	114.0	C3B—C7B—H7BA	115.2
C8A—C7A—H7AA	114.0	C8B—C7B—H7BA	115.2
C13A—C8A—C9A	117.67 (17)	C13B—C8B—C9B	117.56 (16)
C13A—C8A—C7A	125.01 (16)	C13B—C8B—C7B	124.16 (16)
C9A—C8A—C7A	117.16 (17)	C9B—C8B—C7B	118.23 (16)
C10A—C9A—C8A	122.13 (18)	C10B—C9B—C8B	121.70 (17)
C10A—C9A—H9AA	118.9	C10B—C9B—H9BA	119.1
C8A—C9A—H9AA	118.9	C8B—C9B—H9BA	119.1
C9A—C10A—C11A	118.51 (17)	C9B—C10B—C11B	118.80 (17)
C9A—C10A—H10A	120.7	C9B—C10B—H10B	120.6
C11A—C10A—H10A	120.7	C11B—C10B—H10B	120.6
C10A—C11A—C12A	121.59 (17)	C10B—C11B—C12B	121.21 (17)
C10A—C11A—Cl1A	118.99 (14)	C10B—C11B—Cl1B	119.43 (14)
C12A—C11A—Cl1A	119.40 (15)	C12B—C11B—Cl1B	119.33 (15)
C13A—C12A—C11A	119.25 (18)	C13B—C12B—C11B	119.37 (17)
C13A—C12A—H12A	120.4	C13B—C12B—H12B	120.3
C11A—C12A—H12A	120.4	C11B—C12B—H12B	120.3
C12A—C13A—C8A	120.83 (17)	C12B—C13B—C8B	121.32 (17)
C12A—C13A—H13A	119.6	C12B—C13B—H13B	119.3
C8A—C13A—H13A	119.6	C8B—C13B—H13B	119.3
C5A—C14A—C15A	129.81 (16)	C5B—C14B—C15B	130.51 (16)
C5A—C14A—H14A	115.1	C5B—C14B—H14B	114.7
C15A—C14A—H14A	115.1	C15B—C14B—H14B	114.7
C16A—C15A—C20A	117.86 (17)	C16B—C15B—C20B	117.61 (16)
C16A—C15A—C14A	116.56 (16)	C16B—C15B—C14B	117.40 (15)
C20A—C15A—C14A	125.56 (17)	C20B—C15B—C14B	124.93 (16)
C17A—C16A—C15A	121.75 (17)	C17B—C16B—C15B	121.57 (16)
C17A—C16A—H16A	119.1	C17B—C16B—H16B	119.2
C15A—C16A—H16A	119.1	C15B—C16B—H16B	119.2
C16A—C17A—C18A	118.90 (18)	C16B—C17B—C18B	118.99 (16)
C16A—C17A—H17A	120.5	C16B—C17B—H17B	120.5
C18A—C17A—H17A	120.5	C18B—C17B—H17B	120.5
C17A—C18A—C19A	120.95 (17)	C19B—C18B—C17B	121.11 (16)
C17A—C18A—Cl2A	118.89 (15)	C19B—C18B—Cl2B	119.42 (14)
C19A—C18A—Cl2A	120.16 (14)	C17B—C18B—Cl2B	119.47 (14)
C20A—C19A—C18A	119.41 (16)	C20B—C19B—C18B	119.43 (16)
C20A—C19A—H19A	120.3	C20B—C19B—H19B	120.3
C18A—C19A—H19A	120.3	C18B—C19B—H19B	120.3
C19A—C20A—C15A	121.08 (17)	C19B—C20B—C15B	121.20 (16)
C19A—C20A—H20A	119.5	C19B—C20B—H20B	119.4
C15A—C20A—H20A	119.5	C15B—C20B—H20B	119.4
C22A—C21A—C26A	118.64 (16)	C22B—C21B—C26B	118.14 (17)
C22A—C21A—C1A	121.36 (16)	C22B—C21B—C1B	120.62 (16)
C26A—C21A—C1A	119.98 (15)	C26B—C21B—C1B	121.24 (16)
C23A—C22A—C21A	120.60 (17)	C23B—C22B—C21B	121.22 (18)
C23A—C22A—H22A	119.7	C23B—C22B—H22B	119.4
C21A—C22A—H22A	119.7	C21B—C22B—H22B	119.4
C24A—C23A—C22A	120.22 (17)	C24B—C23B—C22B	119.57 (18)
C24A—C23A—H23A	119.9	C24B—C23B—H23B	120.2
C22A—C23A—H23A	119.9	C22B—C23B—H23B	120.2
C23A—C24A—C25A	119.49 (17)	C25B—C24B—C23B	120.06 (18)
C23A—C24A—H24A	120.3	C25B—C24B—H24B	120.0
C25A—C24A—H24A	120.3	C23B—C24B—H24B	120.0
C26A—C25A—C24A	120.30 (17)	C24B—C25B—C26B	120.25 (19)
C26A—C25A—H25A	119.9	C24B—C25B—H25B	119.9
C24A—C25A—H25A	119.8	C26B—C25B—H25B	119.9
C25A—C26A—C21A	120.73 (16)	C25B—C26B—C21B	120.76 (18)
C25A—C26A—H26A	119.6	C25B—C26B—H26B	119.6
C21A—C26A—H26A	119.6	C21B—C26B—H26B	119.6
C6A—N1A—C1A—C21A	163.42 (14)	C6B—N1B—C1B—C21B	64.13 (19)
C2A—N1A—C1A—C21A	−74.36 (18)	C2B—N1B—C1B—C21B	−61.88 (19)
C6A—N1A—C2A—C3A	−63.95 (17)	C6B—N1B—C2B—C3B	66.43 (17)
C1A—N1A—C2A—C3A	173.49 (14)	C1B—N1B—C2B—C3B	−166.71 (14)
N1A—C2A—C3A—C7A	−151.02 (17)	N1B—C2B—C3B—C7B	148.23 (18)
N1A—C2A—C3A—C4A	28.7 (2)	N1B—C2B—C3B—C4B	−30.7 (2)
O1A—O1A—C4A—C5A	0.0 (3)	O1B—O1B—C4B—C5B	0.0 (2)
O1A—O1A—C4A—C3A	0.0 (3)	O1B—O1B—C4B—C3B	0.0 (3)
C7A—C3A—C4A—O1A	1.2 (3)	C7B—C3B—C4B—O1B	−2.5 (3)
C2A—C3A—C4A—O1A	−178.50 (16)	C2B—C3B—C4B—O1B	176.6 (2)
C7A—C3A—C4A—O1A	1.2 (3)	C7B—C3B—C4B—O1B	−2.5 (3)
C2A—C3A—C4A—O1A	−178.50 (16)	C2B—C3B—C4B—O1B	176.6 (2)
C7A—C3A—C4A—C5A	−177.55 (15)	C7B—C3B—C4B—C5B	175.28 (17)
C2A—C3A—C4A—C5A	2.7 (2)	C2B—C3B—C4B—C5B	−5.7 (3)
O1A—C4A—C5A—C14A	3.9 (3)	O1B—C4B—C5B—C14B	6.4 (3)
O1A—C4A—C5A—C14A	3.9 (3)	O1B—C4B—C5B—C14B	6.4 (3)
C3A—C4A—C5A—C14A	−177.34 (15)	C3B—C4B—C5B—C14B	−171.31 (17)
O1A—C4A—C5A—C6A	−179.84 (16)	O1B—C4B—C5B—C6B	−172.3 (2)
O1A—C4A—C5A—C6A	−179.84 (16)	O1B—C4B—C5B—C6B	−172.3 (2)
C3A—C4A—C5A—C6A	−1.1 (2)	C3B—C4B—C5B—C6B	9.9 (3)
C2A—N1A—C6A—C5A	65.66 (18)	C2B—N1B—C6B—C5B	−62.09 (18)
C1A—N1A—C6A—C5A	−171.47 (14)	C1B—N1B—C6B—C5B	171.20 (14)
C14A—C5A—C6A—N1A	143.83 (17)	C14B—C5B—C6B—N1B	−155.89 (17)
C4A—C5A—C6A—N1A	−32.1 (2)	C4B—C5B—C6B—N1B	22.7 (2)
C4A—C3A—C7A—C8A	174.85 (17)	C4B—C3B—C7B—C8B	−178.06 (18)
C2A—C3A—C7A—C8A	−5.5 (3)	C2B—C3B—C7B—C8B	3.0 (3)
C3A—C7A—C8A—C13A	−19.2 (3)	C3B—C7B—C8B—C13B	25.4 (3)
C3A—C7A—C8A—C9A	165.48 (18)	C3B—C7B—C8B—C9B	−157.34 (19)
C13A—C8A—C9A—C10A	0.3 (3)	C13B—C8B—C9B—C10B	−2.4 (3)
C7A—C8A—C9A—C10A	175.98 (16)	C7B—C8B—C9B—C10B	−179.87 (17)
C8A—C9A—C10A—C11A	0.2 (3)	C8B—C9B—C10B—C11B	1.5 (3)
C9A—C10A—C11A—C12A	0.1 (3)	C9B—C10B—C11B—C12B	0.3 (3)
C9A—C10A—C11A—Cl1A	−178.20 (14)	C9B—C10B—C11B—Cl1B	178.39 (14)
C10A—C11A—C12A—C13A	−0.9 (3)	C10B—C11B—C12B—C13B	−1.0 (3)
Cl1A—C11A—C12A—C13A	177.40 (14)	Cl1B—C11B—C12B—C13B	−179.10 (14)
C11A—C12A—C13A—C8A	1.4 (3)	C11B—C12B—C13B—C8B	0.0 (3)
C9A—C8A—C13A—C12A	−1.1 (3)	C9B—C8B—C13B—C12B	1.7 (3)
C7A—C8A—C13A—C12A	−176.41 (17)	C7B—C8B—C13B—C12B	178.97 (17)
C4A—C5A—C14A—C15A	178.45 (16)	C4B—C5B—C14B—C15B	178.23 (18)
C6A—C5A—C14A—C15A	2.5 (3)	C6B—C5B—C14B—C15B	−3.1 (3)
C5A—C14A—C15A—C16A	−153.04 (19)	C5B—C14B—C15B—C16B	160.85 (19)
C5A—C14A—C15A—C20A	28.7 (3)	C5B—C14B—C15B—C20B	−22.0 (3)
C20A—C15A—C16A—C17A	−1.7 (3)	C20B—C15B—C16B—C17B	2.8 (3)
C14A—C15A—C16A—C17A	179.90 (16)	C14B—C15B—C16B—C17B	−179.86 (16)
C15A—C16A—C17A—C18A	2.1 (3)	C15B—C16B—C17B—C18B	−1.8 (3)
C16A—C17A—C18A—C19A	−0.8 (3)	C16B—C17B—C18B—C19B	−0.8 (3)
C16A—C17A—C18A—Cl2A	178.13 (14)	C16B—C17B—C18B—Cl2B	178.72 (14)
C17A—C18A—C19A—C20A	−0.8 (3)	C17B—C18B—C19B—C20B	2.5 (3)
Cl2A—C18A—C19A—C20A	−179.76 (13)	Cl2B—C18B—C19B—C20B	−177.08 (14)
C18A—C19A—C20A—C15A	1.2 (3)	C18B—C19B—C20B—C15B	−1.5 (3)
C16A—C15A—C20A—C19A	0.0 (3)	C16B—C15B—C20B—C19B	−1.1 (3)
C14A—C15A—C20A—C19A	178.24 (16)	C14B—C15B—C20B—C19B	−178.24 (17)
N1A—C1A—C21A—C22A	120.53 (17)	N1B—C1B—C21B—C22B	85.3 (2)
N1A—C1A—C21A—C26A	−61.1 (2)	N1B—C1B—C21B—C26B	−94.30 (19)
C26A—C21A—C22A—C23A	−1.1 (3)	C26B—C21B—C22B—C23B	1.1 (3)
C1A—C21A—C22A—C23A	177.27 (16)	C1B—C21B—C22B—C23B	−178.52 (16)
C21A—C22A—C23A—C24A	0.7 (3)	C21B—C22B—C23B—C24B	−1.0 (3)
C22A—C23A—C24A—C25A	0.3 (3)	C22B—C23B—C24B—C25B	0.5 (3)
C23A—C24A—C25A—C26A	−0.9 (3)	C23B—C24B—C25B—C26B	−0.1 (3)
C24A—C25A—C26A—C21A	0.5 (3)	C24B—C25B—C26B—C21B	0.2 (3)
C22A—C21A—C26A—C25A	0.5 (2)	C22B—C21B—C26B—C25B	−0.7 (3)
C1A—C21A—C26A—C25A	−177.93 (16)	C1B—C21B—C26B—C25B	178.92 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16B—H16B···O1A	0.95	2.42	3.334 (2)	160
C14A—H14A···O1B	0.95	2.52	3.309 (2)	141
C16A—H16A···O1B	0.95	2.48	3.099 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16B—H16B⋯O1A	0.95	2.42	3.334 (2)	160
C14A—H14A⋯O1B	0.95	2.52	3.309 (2)	141
C16A—H16A⋯O1B	0.95	2.48	3.099 (2)	122