N'-[(E)-4-Chloro-benzyl-idene]-2-(4-isobutyl-phen-yl)propanohydrazide.

The asymmetric unit of title compound, C(20)H(23)ClN(2)O, consists of two crystallographically independent mol-ecules (A and B) in which the orientations of the 4-isobutyl-phenyl units are different. The isobutyl group of mol-ecule B is disordered over two positions with occupancies of 0.850 (5) and 0.150 (5). The dihedral angle between the two benzene rings is 88.70 (9)° in mol-ecule A and 89.38 (9)° in mol-ecule B. The independent mol-ecules are linked together into chains along [100] by N-H⋯O and C-H⋯O hydrogen bonds, and by C-H⋯π inter-actions. In the chain, N-H⋯O and C-H⋯O hydrogen bonds generate R(2) (1)(6) ring motifs. In addition, C-H⋯N hydrogen bonds are observed. The presence of pseudosymmetry in the structure suggests the higher symmetry space group Pbca but attempts to refine the structure in this space group resulted in high R (0.119) and wR (0.296) values.

Related literature

For general background and biological applications of hydrazone compounds, see: Kawail et al. (2005 ▶); Klasser & Epstein, (2005 ▶); Sridhar & Perumal (2003 ▶); Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy, (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the crystal structure of the bromo analogue, see: Fun et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H23ClN2O

M = 342.85

Orthorhombic,

a = 9.1405 (1) Å

b = 11.9260 (2) Å

c = 33.3487 (5) Å

V = 3635.33 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.56 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.887, T max = 0.967

26510 measured reflections

10652 independent reflections

8888 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.02

10652 reflections

453 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 4712 Friedel pairs

Flack parameter: 0.10 (5)

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/S1600536809015906/ci2793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015906/ci2793Isup2.hkl

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

C20H23ClN2O	F(000) = 1456
Mr = 342.85	Dx = 1.253 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7618 reflections
a = 9.1405 (1) Å	θ = 2.4–30.0°
b = 11.9260 (2) Å	µ = 0.22 mm−1
c = 33.3487 (5) Å	T = 100 K
V = 3635.33 (9) Å3	Block, colourless
Z = 8	0.56 × 0.18 × 0.15 mm

Bruker SMART APEXII CCD area-detector diffractometer	10652 independent reflections
Radiation source: fine-focus sealed tube	8888 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 30.1°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.887, Tmax = 0.967	k = −13→16
26510 measured reflections	l = −46→46

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.6608P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
10652 reflections	Δρmax = 0.28 e Å−3
453 parameters	Δρmin = −0.25 e Å−3
0 restraints	Absolute structure: Flack (1983), 4712 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (5)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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	Occ. (<1)
Cl1A	0.85958 (7)	−0.01289 (4)	0.079925 (15)	0.03026 (12)
O1A	0.87919 (14)	0.49658 (12)	0.27831 (4)	0.0223 (3)
N1A	0.72753 (18)	0.36296 (13)	0.22621 (5)	0.0175 (3)
N2A	0.66284 (18)	0.44256 (13)	0.25054 (4)	0.0172 (3)
H1NA	0.5699	0.4534	0.2493	0.021*
C1A	0.8193 (2)	0.16989 (16)	0.17979 (5)	0.0191 (4)
H1AA	0.8688	0.1789	0.2039	0.023*
C2A	0.8699 (2)	0.09272 (16)	0.15182 (6)	0.0215 (4)
H2AA	0.9526	0.0497	0.1571	0.026*
C3A	0.7946 (2)	0.08102 (16)	0.11585 (6)	0.0215 (4)
C4A	0.6700 (2)	0.14204 (16)	0.10760 (6)	0.0227 (4)
H4AA	0.6206	0.1324	0.0835	0.027*
C5A	0.6195 (2)	0.21807 (16)	0.13586 (6)	0.0207 (4)
H5AA	0.5346	0.2587	0.1307	0.025*
C6A	0.6943 (2)	0.23433 (16)	0.17187 (5)	0.0181 (4)
C7A	0.6421 (2)	0.32052 (15)	0.19980 (5)	0.0184 (4)
H7AA	0.5456	0.3447	0.1983	0.022*
C8A	0.7450 (2)	0.50325 (15)	0.27615 (5)	0.0164 (4)
C9A	0.6584 (2)	0.58104 (15)	0.30371 (5)	0.0161 (3)
H9AA	0.5618	0.5933	0.2917	0.019*
C10A	0.6374 (2)	0.51916 (15)	0.34336 (5)	0.0173 (3)
C11A	0.5317 (2)	0.43554 (16)	0.34657 (6)	0.0186 (4)
H11A	0.4730	0.4188	0.3246	0.022*
C12A	0.5130 (2)	0.37699 (16)	0.38200 (6)	0.0207 (4)
H12A	0.4411	0.3219	0.3834	0.025*
C13A	0.5986 (2)	0.39827 (16)	0.41551 (5)	0.0204 (4)
C14A	0.7039 (2)	0.48227 (17)	0.41241 (6)	0.0233 (4)
H14A	0.7624	0.4987	0.4345	0.028*
C15A	0.7232 (2)	0.54207 (16)	0.37695 (5)	0.0212 (4)
H15A	0.7941	0.5979	0.3756	0.025*
C16A	0.5822 (2)	0.32870 (16)	0.45308 (6)	0.0247 (4)
H16A	0.4792	0.3226	0.4597	0.030*
H16B	0.6305	0.3668	0.4751	0.030*
C17A	0.6470 (2)	0.21025 (16)	0.44874 (6)	0.0235 (4)
H17A	0.5996	0.1738	0.4258	0.028*
C18A	0.8110 (2)	0.21425 (19)	0.44058 (7)	0.0314 (5)
H18A	0.8470	0.1395	0.4364	0.047*
H18B	0.8602	0.2472	0.4631	0.047*
H18C	0.8292	0.2586	0.4171	0.047*
C19A	0.6155 (3)	0.14012 (19)	0.48615 (6)	0.0357 (5)
H19A	0.6571	0.0668	0.4830	0.053*
H19B	0.5116	0.1337	0.4898	0.053*
H19C	0.6579	0.1759	0.5092	0.053*
C20A	0.7355 (2)	0.69465 (16)	0.30705 (6)	0.0203 (4)
H20A	0.6858	0.7403	0.3265	0.030*
H20B	0.7338	0.7315	0.2815	0.030*
H20C	0.8350	0.6834	0.3153	0.030*
Cl1B	0.35621 (6)	−0.01924 (4)	0.418134 (16)	0.03065 (12)
O1B	0.38166 (14)	0.50246 (12)	0.22302 (4)	0.0224 (3)
N1B	0.23212 (17)	0.37147 (13)	0.27639 (5)	0.0183 (3)
N2B	0.16586 (18)	0.44848 (14)	0.25107 (4)	0.0189 (3)
H1NB	0.0729	0.4590	0.2523	0.023*
C1B	0.3149 (2)	0.17172 (17)	0.32054 (6)	0.0210 (4)
H1BA	0.3605	0.1792	0.2958	0.025*
C2B	0.3619 (2)	0.09038 (16)	0.34692 (6)	0.0214 (4)
H2BA	0.4372	0.0419	0.3398	0.026*
C3B	0.2958 (2)	0.08155 (16)	0.38423 (6)	0.0217 (4)
C4B	0.1802 (2)	0.15040 (17)	0.39501 (6)	0.0235 (4)
H4BA	0.1361	0.1433	0.4200	0.028*
C5B	0.1313 (2)	0.22994 (16)	0.36785 (6)	0.0207 (4)
H5BA	0.0522	0.2753	0.3745	0.025*
C6B	0.1994 (2)	0.24292 (15)	0.33062 (5)	0.0178 (4)
C7B	0.1467 (2)	0.33044 (16)	0.30332 (5)	0.0192 (4)
H7BA	0.0511	0.3564	0.3055	0.023*
C8B	0.2472 (2)	0.50689 (16)	0.22453 (5)	0.0177 (4)
C9B	0.1567 (2)	0.57335 (16)	0.19427 (5)	0.0184 (4)
H9BA	0.0596	0.5875	0.2057	0.022*
C10B	0.1401 (2)	0.49807 (15)	0.15762 (5)	0.0166 (3)
C11B	0.0116 (2)	0.43596 (16)	0.15239 (6)	0.0204 (4)
H11B	−0.0652	0.4442	0.1704	0.025*
C12B	−0.0020 (2)	0.36179 (16)	0.12028 (6)	0.0201 (4)
H12B	−0.0889	0.3223	0.1170	0.024*
C13B	0.1114 (2)	0.34555 (15)	0.09307 (5)	0.0189 (4)
C14B	0.2380 (2)	0.40909 (17)	0.09833 (6)	0.0221 (4)
H14B	0.3150	0.4009	0.0803	0.027*
C15B	0.2516 (2)	0.48440 (17)	0.12987 (5)	0.0221 (4)
H15B	0.3369	0.5263	0.1324	0.026*
C16B	0.0976 (2)	0.26297 (16)	0.05913 (5)	0.0225 (4)
H16C	0.0608	0.1938	0.0698	0.027*	0.850 (5)
H16D	0.1935	0.2485	0.0486	0.027*	0.850 (5)
H16E	0.0156	0.2152	0.0647	0.027*	0.150 (5)
H16F	0.1835	0.2167	0.0593	0.027*	0.150 (5)
C17B	−0.0010 (3)	0.2988 (2)	0.02462 (7)	0.0242 (6)	0.850 (5)
H17B	−0.1012	0.3044	0.0348	0.029*	0.850 (5)
C18B	0.0013 (3)	0.2096 (3)	−0.00823 (9)	0.0302 (7)	0.850 (5)
H18D	−0.0631	0.2315	−0.0296	0.045*	0.850 (5)
H18E	−0.0307	0.1392	0.0027	0.045*	0.850 (5)
H18F	0.0990	0.2018	−0.0184	0.045*	0.850 (5)
C19B	0.0411 (5)	0.4117 (2)	0.00756 (8)	0.0498 (10)	0.850 (5)
H19D	0.0312	0.4681	0.0279	0.075*	0.850 (5)
H19E	−0.0219	0.4295	−0.0146	0.075*	0.850 (5)
H19F	0.1407	0.4093	−0.0015	0.075*	0.850 (5)
C17C	0.0720 (16)	0.3086 (10)	0.0176 (4)	0.014 (2)*	0.150 (5)
H17C	0.1601	0.3497	0.0095	0.017*	0.150 (5)
C18C	0.0557 (15)	0.2076 (14)	−0.0106 (5)	0.014 (2)*	0.15
H18G	0.1379	0.1583	−0.0073	0.021*	0.150 (5)
H18H	0.0518	0.2332	−0.0379	0.021*	0.150 (5)
H18I	−0.0328	0.1680	−0.0043	0.021*	0.150 (5)
C19C	−0.0562 (16)	0.3885 (12)	0.0151 (4)	0.023 (3)*	0.150 (5)
H19G	−0.0360	0.4539	0.0309	0.035*	0.150 (5)
H19H	−0.1425	0.3522	0.0251	0.035*	0.150 (5)
H19I	−0.0714	0.4101	−0.0123	0.035*	0.150 (5)
C20B	0.2306 (2)	0.68628 (17)	0.18538 (6)	0.0234 (4)
H20D	0.2272	0.7327	0.2089	0.035*
H20E	0.1802	0.7230	0.1638	0.035*
H20F	0.3307	0.6738	0.1779	0.035*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0455 (3)	0.0200 (2)	0.0253 (2)	−0.0009 (2)	0.0077 (2)	−0.0070 (2)
O1A	0.0167 (6)	0.0280 (7)	0.0221 (7)	0.0015 (6)	−0.0005 (5)	−0.0034 (6)
N1A	0.0202 (7)	0.0167 (7)	0.0157 (7)	0.0004 (6)	0.0024 (6)	−0.0009 (6)
N2A	0.0159 (8)	0.0183 (8)	0.0173 (7)	0.0035 (6)	−0.0023 (6)	−0.0022 (6)
C1A	0.0247 (10)	0.0162 (9)	0.0163 (9)	−0.0019 (8)	−0.0005 (8)	0.0012 (7)
C2A	0.0259 (10)	0.0167 (9)	0.0219 (9)	0.0005 (8)	0.0050 (8)	0.0019 (7)
C3A	0.0316 (10)	0.0146 (9)	0.0183 (9)	−0.0041 (8)	0.0048 (8)	−0.0033 (8)
C4A	0.0300 (10)	0.0201 (10)	0.0179 (9)	−0.0050 (8)	−0.0008 (8)	−0.0021 (8)
C5A	0.0222 (10)	0.0190 (9)	0.0211 (9)	−0.0042 (8)	−0.0002 (8)	0.0009 (7)
C6A	0.0209 (10)	0.0168 (9)	0.0167 (8)	−0.0033 (7)	0.0015 (7)	0.0017 (7)
C7A	0.0190 (8)	0.0182 (9)	0.0181 (8)	−0.0018 (8)	0.0001 (7)	0.0011 (7)
C8A	0.0188 (9)	0.0162 (9)	0.0143 (8)	0.0017 (7)	−0.0011 (7)	0.0016 (7)
C9A	0.0171 (8)	0.0167 (8)	0.0146 (8)	0.0022 (7)	−0.0001 (7)	0.0007 (7)
C10A	0.0193 (8)	0.0153 (8)	0.0171 (8)	0.0028 (7)	−0.0001 (7)	−0.0008 (7)
C11A	0.0188 (9)	0.0174 (9)	0.0197 (9)	0.0013 (7)	−0.0020 (7)	−0.0021 (7)
C12A	0.0201 (9)	0.0160 (9)	0.0259 (10)	−0.0024 (7)	0.0032 (8)	−0.0016 (8)
C13A	0.0272 (9)	0.0166 (9)	0.0175 (8)	0.0009 (7)	0.0051 (7)	0.0006 (7)
C14A	0.0286 (10)	0.0252 (10)	0.0161 (8)	−0.0054 (8)	−0.0029 (7)	−0.0001 (7)
C15A	0.0235 (9)	0.0208 (9)	0.0193 (9)	−0.0073 (8)	−0.0002 (7)	−0.0004 (7)
C16A	0.0336 (10)	0.0217 (9)	0.0189 (9)	0.0003 (8)	0.0056 (8)	0.0010 (8)
C17A	0.0304 (10)	0.0198 (9)	0.0203 (9)	0.0000 (8)	0.0009 (8)	0.0018 (7)
C18A	0.0295 (11)	0.0303 (11)	0.0344 (11)	0.0014 (9)	−0.0031 (9)	0.0033 (9)
C19A	0.0532 (14)	0.0260 (11)	0.0278 (11)	0.0021 (10)	0.0060 (10)	0.0099 (9)
C20A	0.0242 (9)	0.0162 (9)	0.0205 (9)	0.0001 (7)	0.0007 (7)	0.0021 (7)
Cl1B	0.0338 (3)	0.0233 (2)	0.0348 (3)	0.0022 (2)	−0.0057 (2)	0.0096 (2)
O1B	0.0165 (6)	0.0305 (8)	0.0202 (6)	0.0027 (6)	−0.0005 (5)	0.0010 (6)
N1B	0.0198 (8)	0.0185 (8)	0.0164 (7)	0.0032 (6)	−0.0025 (6)	−0.0019 (6)
N2B	0.0157 (8)	0.0225 (9)	0.0186 (8)	0.0040 (7)	−0.0030 (6)	0.0008 (6)
C1B	0.0202 (9)	0.0222 (10)	0.0207 (9)	0.0012 (8)	−0.0011 (8)	−0.0035 (8)
C2B	0.0200 (9)	0.0164 (9)	0.0279 (10)	0.0009 (8)	−0.0007 (8)	−0.0032 (8)
C3B	0.0226 (9)	0.0162 (9)	0.0262 (10)	−0.0016 (8)	−0.0058 (8)	0.0020 (8)
C4B	0.0255 (10)	0.0238 (10)	0.0213 (9)	−0.0026 (8)	0.0000 (8)	0.0005 (8)
C5B	0.0188 (9)	0.0187 (9)	0.0245 (9)	0.0019 (8)	0.0019 (8)	−0.0006 (7)
C6B	0.0173 (9)	0.0167 (9)	0.0194 (9)	0.0003 (7)	−0.0032 (7)	0.0000 (7)
C7B	0.0176 (8)	0.0195 (9)	0.0206 (9)	0.0036 (8)	−0.0024 (8)	−0.0019 (7)
C8B	0.0193 (9)	0.0188 (9)	0.0150 (8)	0.0004 (8)	−0.0013 (7)	−0.0045 (7)
C9B	0.0169 (8)	0.0196 (9)	0.0187 (8)	0.0016 (8)	−0.0021 (7)	−0.0001 (7)
C10B	0.0189 (8)	0.0173 (9)	0.0138 (7)	0.0013 (7)	−0.0022 (7)	0.0021 (7)
C11B	0.0182 (9)	0.0234 (10)	0.0196 (9)	−0.0026 (8)	−0.0001 (7)	0.0011 (8)
C12B	0.0208 (9)	0.0185 (9)	0.0210 (9)	−0.0063 (7)	−0.0015 (7)	0.0018 (7)
C13B	0.0232 (9)	0.0166 (8)	0.0171 (8)	0.0013 (7)	−0.0040 (7)	0.0012 (7)
C14B	0.0202 (8)	0.0282 (10)	0.0181 (9)	0.0001 (8)	0.0010 (7)	−0.0026 (8)
C15B	0.0177 (8)	0.0285 (10)	0.0201 (9)	−0.0043 (8)	−0.0012 (7)	−0.0011 (8)
C16B	0.0272 (9)	0.0192 (9)	0.0211 (9)	0.0010 (8)	−0.0054 (7)	−0.0023 (7)
C17B	0.0253 (14)	0.0268 (13)	0.0203 (11)	0.0026 (10)	−0.0055 (10)	−0.0049 (9)
C18B	0.0330 (15)	0.0326 (15)	0.0251 (13)	−0.0039 (14)	−0.0069 (13)	−0.0105 (11)
C19B	0.101 (3)	0.0250 (14)	0.0231 (13)	0.0006 (17)	−0.0188 (17)	−0.0003 (11)
C20B	0.0252 (10)	0.0195 (9)	0.0255 (10)	−0.0006 (8)	−0.0045 (8)	−0.0016 (8)

Cl1A—C3A	1.744 (2)	C1B—C2B	1.378 (3)
O1A—C8A	1.231 (2)	C1B—C6B	1.395 (3)
N1A—C7A	1.281 (2)	C1B—H1BA	0.93
N1A—N2A	1.382 (2)	C2B—C3B	1.387 (3)
N2A—C8A	1.348 (2)	C2B—H2BA	0.93
N2A—H1NA	0.86	C3B—C4B	1.386 (3)
C1A—C2A	1.390 (3)	C4B—C5B	1.386 (3)
C1A—C6A	1.402 (3)	C4B—H4BA	0.93
C1A—H1AA	0.93	C5B—C6B	1.397 (3)
C2A—C3A	1.390 (3)	C5B—H5BA	0.93
C2A—H2AA	0.93	C6B—C7B	1.467 (3)
C3A—C4A	1.379 (3)	C7B—H7BA	0.93
C4A—C5A	1.387 (3)	C8B—C9B	1.527 (3)
C4A—H4AA	0.93	C9B—C10B	1.524 (2)
C5A—C6A	1.396 (3)	C9B—C20B	1.536 (3)
C5A—H5AA	0.93	C9B—H9BA	0.98
C6A—C7A	1.467 (3)	C10B—C15B	1.386 (3)
C7A—H7AA	0.93	C10B—C11B	1.400 (3)
C8A—C9A	1.527 (2)	C11B—C12B	1.394 (3)
C9A—C10A	1.526 (2)	C11B—H11B	0.93
C9A—C20A	1.531 (3)	C12B—C13B	1.392 (3)
C9A—H9AA	0.98	C12B—H12B	0.93
C10A—C11A	1.393 (3)	C13B—C14B	1.394 (3)
C10A—C15A	1.394 (2)	C13B—C16B	1.506 (2)
C11A—C12A	1.383 (3)	C14B—C15B	1.389 (3)
C11A—H11A	0.93	C14B—H14B	0.93
C12A—C13A	1.387 (3)	C15B—H15B	0.93
C12A—H12A	0.93	C16B—C17C	1.507 (12)
C13A—C14A	1.393 (3)	C16B—C17B	1.523 (3)
C13A—C16A	1.510 (2)	C16B—H16C	0.96
C14A—C15A	1.392 (3)	C16B—H16D	0.96
C14A—H14A	0.93	C16B—H16E	0.96
C15A—H15A	0.93	C16B—H16F	0.96
C16A—C17A	1.539 (3)	C17B—C19B	1.511 (4)
C16A—H16A	0.97	C17B—C18B	1.528 (3)
C16A—H16B	0.97	C17B—H17B	0.98
C17A—C18A	1.524 (3)	C18B—H18D	0.96
C17A—C19A	1.529 (3)	C18B—H18E	0.96
C17A—H17A	0.98	C18B—H18F	0.96
C18A—H18A	0.96	C19B—H19D	0.96
C18A—H18B	0.96	C19B—H19E	0.96
C18A—H18C	0.96	C19B—H19F	0.96
C19A—H19A	0.96	C17C—C19C	1.513 (19)
C19A—H19B	0.96	C17C—C18C	1.535 (19)
C19A—H19C	0.96	C17C—H17C	0.98
C20A—H20A	0.96	C18C—H18G	0.96
C20A—H20B	0.96	C18C—H18H	0.96
C20A—H20C	0.96	C18C—H18I	0.96
Cl1B—C3B	1.740 (2)	C19C—H19G	0.96
O1B—C8B	1.231 (2)	C19C—H19H	0.96
N1B—C7B	1.287 (2)	C19C—H19I	0.96
N1B—N2B	1.387 (2)	C20B—H20D	0.96
N2B—C8B	1.350 (2)	C20B—H20E	0.96
N2B—H1NB	0.86	C20B—H20F	0.96
C7A—N1A—N2A	114.48 (16)	C1B—C2B—H2BA	120.3
C8A—N2A—N1A	120.17 (15)	C3B—C2B—H2BA	120.3
C8A—N2A—H1NA	119.9	C4B—C3B—C2B	121.32 (18)
N1A—N2A—H1NA	119.9	C4B—C3B—Cl1B	118.85 (16)
C2A—C1A—C6A	120.52 (18)	C2B—C3B—Cl1B	119.82 (15)
C2A—C1A—H1AA	119.7	C5B—C4B—C3B	118.79 (18)
C6A—C1A—H1AA	119.7	C5B—C4B—H4BA	120.6
C1A—C2A—C3A	118.74 (19)	C3B—C4B—H4BA	120.6
C1A—C2A—H2AA	120.6	C4B—C5B—C6B	120.88 (18)
C3A—C2A—H2AA	120.6	C4B—C5B—H5BA	119.6
C4A—C3A—C2A	121.88 (18)	C6B—C5B—H5BA	119.6
C4A—C3A—Cl1A	118.90 (15)	C1B—C6B—C5B	118.92 (17)
C2A—C3A—Cl1A	119.22 (16)	C1B—C6B—C7B	122.13 (17)
C3A—C4A—C5A	118.98 (18)	C5B—C6B—C7B	118.95 (17)
C3A—C4A—H4AA	120.5	N1B—C7B—C6B	120.31 (18)
C5A—C4A—H4AA	120.5	N1B—C7B—H7BA	119.8
C4A—C5A—C6A	120.82 (19)	C6B—C7B—H7BA	119.8
C4A—C5A—H5AA	119.6	O1B—C8B—N2B	123.68 (18)
C6A—C5A—H5AA	119.6	O1B—C8B—C9B	122.43 (17)
C5A—C6A—C1A	119.03 (18)	N2B—C8B—C9B	113.76 (16)
C5A—C6A—C7A	118.98 (18)	C10B—C9B—C8B	106.14 (15)
C1A—C6A—C7A	121.98 (17)	C10B—C9B—C20B	113.93 (15)
N1A—C7A—C6A	121.01 (18)	C8B—C9B—C20B	110.15 (15)
N1A—C7A—H7AA	119.5	C10B—C9B—H9BA	108.8
C6A—C7A—H7AA	119.5	C8B—C9B—H9BA	108.8
O1A—C8A—N2A	123.87 (17)	C20B—C9B—H9BA	108.8
O1A—C8A—C9A	121.34 (17)	C15B—C10B—C11B	118.13 (17)
N2A—C8A—C9A	114.77 (15)	C15B—C10B—C9B	122.11 (17)
C10A—C9A—C8A	107.03 (14)	C11B—C10B—C9B	119.69 (17)
C10A—C9A—C20A	115.01 (15)	C12B—C11B—C10B	120.44 (18)
C8A—C9A—C20A	110.07 (15)	C12B—C11B—H11B	119.8
C10A—C9A—H9AA	108.2	C10B—C11B—H11B	119.8
C8A—C9A—H9AA	108.2	C13B—C12B—C11B	121.48 (18)
C20A—C9A—H9AA	108.2	C13B—C12B—H12B	119.3
C11A—C10A—C15A	117.96 (17)	C11B—C12B—H12B	119.3
C11A—C10A—C9A	119.99 (16)	C12B—C13B—C14B	117.44 (17)
C15A—C10A—C9A	122.04 (17)	C12B—C13B—C16B	121.24 (17)
C12A—C11A—C10A	120.86 (18)	C14B—C13B—C16B	121.32 (17)
C12A—C11A—H11A	119.6	C15B—C14B—C13B	121.42 (17)
C10A—C11A—H11A	119.6	C15B—C14B—H14B	119.3
C11A—C12A—C13A	121.73 (18)	C13B—C14B—H14B	119.3
C11A—C12A—H12A	119.1	C10B—C15B—C14B	121.04 (17)
C13A—C12A—H12A	119.1	C10B—C15B—H15B	119.5
C12A—C13A—C14A	117.48 (17)	C14B—C15B—H15B	119.5
C12A—C13A—C16A	120.79 (17)	C13B—C16B—C17C	117.9 (5)
C14A—C13A—C16A	121.67 (17)	C13B—C16B—C17B	115.73 (16)
C15A—C14A—C13A	121.26 (17)	C13B—C16B—H16C	108.2
C15A—C14A—H14A	119.4	C17C—C16B—H16C	126.7
C13A—C14A—H14A	119.4	C17B—C16B—H16C	108.4
C14A—C15A—C10A	120.71 (17)	C13B—C16B—H16D	108.4
C14A—C15A—H15A	119.6	C17B—C16B—H16D	108.3
C10A—C15A—H15A	119.6	H16C—C16B—H16D	107.5
C13A—C16A—C17A	112.86 (15)	C13B—C16B—H16E	107.9
C13A—C16A—H16A	109.0	C17C—C16B—H16E	105.8
C17A—C16A—H16A	109.0	H16D—C16B—H16E	132.7
C13A—C16A—H16B	109.0	C13B—C16B—H16F	107.7
C17A—C16A—H16B	109.0	C17C—C16B—H16F	109.8
H16A—C16A—H16B	107.8	C17B—C16B—H16F	130.5
C18A—C17A—C19A	110.38 (18)	H16E—C16B—H16F	107.3
C18A—C17A—C16A	111.51 (17)	C19B—C17B—C16B	112.6 (2)
C19A—C17A—C16A	110.67 (16)	C19B—C17B—C18B	110.3 (2)
C18A—C17A—H17A	108.1	C16B—C17B—C18B	109.8 (2)
C19A—C17A—H17A	108.1	C19B—C17B—H17B	108.0
C16A—C17A—H17A	108.1	C16B—C17B—H17B	108.0
C17A—C18A—H18A	109.5	C18B—C17B—H17B	108.0
C17A—C18A—H18B	109.5	C16B—C17C—C19C	113.4 (10)
H18A—C18A—H18B	109.5	C16B—C17C—C18C	107.2 (10)
C17A—C18A—H18C	109.5	C19C—C17C—C18C	112.7 (11)
H18A—C18A—H18C	109.5	C16B—C17C—H17C	107.8
H18B—C18A—H18C	109.5	C19C—C17C—H17C	107.8
C17A—C19A—H19A	109.5	C18C—C17C—H17C	107.8
C17A—C19A—H19B	109.5	C17C—C18C—H18G	109.5
H19A—C19A—H19B	109.5	C17C—C18C—H18H	109.5
C17A—C19A—H19C	109.5	H18G—C18C—H18H	109.5
H19A—C19A—H19C	109.5	C17C—C18C—H18I	109.5
H19B—C19A—H19C	109.5	H18G—C18C—H18I	109.5
C9A—C20A—H20A	109.5	H18H—C18C—H18I	109.5
C9A—C20A—H20B	109.5	C17C—C19C—H19G	109.5
H20A—C20A—H20B	109.5	C17C—C19C—H19H	109.5
C9A—C20A—H20C	109.5	H19G—C19C—H19H	109.5
H20A—C20A—H20C	109.5	C17C—C19C—H19I	109.5
H20B—C20A—H20C	109.5	H19G—C19C—H19I	109.5
C7B—N1B—N2B	114.31 (16)	H19H—C19C—H19I	109.5
C8B—N2B—N1B	120.03 (16)	C9B—C20B—H20D	109.5
C8B—N2B—H1NB	120.0	C9B—C20B—H20E	109.5
N1B—N2B—H1NB	120.0	H20D—C20B—H20E	109.5
C2B—C1B—C6B	120.68 (18)	C9B—C20B—H20F	109.5
C2B—C1B—H1BA	119.7	H20D—C20B—H20F	109.5
C6B—C1B—H1BA	119.7	H20E—C20B—H20F	109.5
C1B—C2B—C3B	119.36 (18)
C7A—N1A—N2A—C8A	−171.84 (16)	C2B—C3B—C4B—C5B	−0.6 (3)
C6A—C1A—C2A—C3A	0.2 (3)	Cl1B—C3B—C4B—C5B	−179.42 (16)
C1A—C2A—C3A—C4A	−1.3 (3)	C3B—C4B—C5B—C6B	−1.7 (3)
C1A—C2A—C3A—Cl1A	178.34 (15)	C2B—C1B—C6B—C5B	−0.5 (3)
C2A—C3A—C4A—C5A	0.7 (3)	C2B—C1B—C6B—C7B	179.92 (18)
Cl1A—C3A—C4A—C5A	−178.97 (15)	C4B—C5B—C6B—C1B	2.2 (3)
C3A—C4A—C5A—C6A	1.0 (3)	C4B—C5B—C6B—C7B	−178.22 (18)
C4A—C5A—C6A—C1A	−2.1 (3)	N2B—N1B—C7B—C6B	176.26 (16)
C4A—C5A—C6A—C7A	176.25 (17)	C1B—C6B—C7B—N1B	−24.7 (3)
C2A—C1A—C6A—C5A	1.4 (3)	C5B—C6B—C7B—N1B	155.66 (18)
C2A—C1A—C6A—C7A	−176.85 (18)	N1B—N2B—C8B—O1B	−5.5 (3)
N2A—N1A—C7A—C6A	−179.59 (16)	N1B—N2B—C8B—C9B	170.38 (15)
C5A—C6A—C7A—N1A	−158.07 (18)	O1B—C8B—C9B—C10B	82.4 (2)
C1A—C6A—C7A—N1A	20.2 (3)	N2B—C8B—C9B—C10B	−93.60 (18)
N1A—N2A—C8A—O1A	3.6 (3)	O1B—C8B—C9B—C20B	−41.4 (2)
N1A—N2A—C8A—C9A	−175.07 (15)	N2B—C8B—C9B—C20B	142.63 (17)
O1A—C8A—C9A—C10A	−82.3 (2)	C8B—C9B—C10B—C15B	−78.2 (2)
N2A—C8A—C9A—C10A	96.38 (18)	C20B—C9B—C10B—C11B	−140.01 (18)
O1A—C8A—C9A—C20A	43.3 (2)	C20B—C9B—C10B—C15B	43.2 (2)
N2A—C8A—C9A—C20A	−137.99 (16)	C8B—C9B—C10B—C11B	98.61 (19)
C8A—C9A—C10A—C11A	−77.7 (2)	C15B—C10B—C11B—C12B	0.7 (3)
C20A—C9A—C10A—C11A	159.65 (17)	C9B—C10B—C11B—C12B	−176.29 (17)
C8A—C9A—C10A—C15A	101.1 (2)	C10B—C11B—C12B—C13B	1.2 (3)
C20A—C9A—C10A—C15A	−21.5 (3)	C11B—C12B—C13B—C14B	−2.1 (3)
C15A—C10A—C11A—C12A	−0.2 (3)	C11B—C12B—C13B—C16B	178.27 (17)
C9A—C10A—C11A—C12A	178.72 (17)	C12B—C13B—C14B—C15B	1.1 (3)
C10A—C11A—C12A—C13A	−0.5 (3)	C16B—C13B—C14B—C15B	−179.27 (18)
C11A—C12A—C13A—C14A	0.8 (3)	C11B—C10B—C15B—C14B	−1.7 (3)
C11A—C12A—C13A—C16A	−176.36 (18)	C9B—C10B—C15B—C14B	175.23 (17)
C12A—C13A—C14A—C15A	−0.5 (3)	C13B—C14B—C15B—C10B	0.8 (3)
C16A—C13A—C14A—C15A	176.63 (18)	C12B—C13B—C16B—C17C	104.7 (7)
C13A—C14A—C15A—C10A	−0.1 (3)	C14B—C13B—C16B—C17C	−75.0 (7)
C11A—C10A—C15A—C14A	0.5 (3)	C12B—C13B—C16B—C17B	74.0 (3)
C9A—C10A—C15A—C14A	−178.40 (18)	C14B—C13B—C16B—C17B	−105.7 (2)
C12A—C13A—C16A—C17A	73.5 (2)	C13B—C16B—C17B—C19B	54.1 (3)
C14A—C13A—C16A—C17A	−103.5 (2)	C17C—C16B—C17B—C19B	−47.5 (10)
C13A—C16A—C17A—C18A	61.8 (2)	C13B—C16B—C17B—C18B	177.4 (2)
C13A—C16A—C17A—C19A	−174.92 (18)	C17C—C16B—C17B—C18B	75.9 (10)
C7B—N1B—N2B—C8B	172.53 (17)	C13B—C16B—C17C—C19C	−52.6 (12)
C6B—C1B—C2B—C3B	−1.7 (3)	C17B—C16B—C17C—C19C	39.9 (10)
C1B—C2B—C3B—C4B	2.2 (3)	C13B—C16B—C17C—C18C	−177.6 (7)
C1B—C2B—C3B—Cl1B	−178.93 (15)	C17B—C16B—C17C—C18C	−85.1 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···O1B	0.86	2.02	2.821 (2)	155
C7A—H7AA···O1B	0.93	2.54	3.313 (2)	140
C12A—H12A···Cg1	0.93	2.75	3.632 (2)	159
N2B—H1NB···O1Ai	0.86	2.02	2.832 (2)	157
C7B—H7BA···O1Ai	0.93	2.47	3.256 (2)	143
C12B—H12B···Cg2i	0.93	2.65	3.462 (2)	146
C20A—H20B···N1Bii	0.96	2.57	3.504 (3)	164

Table 1

Selected torsion angles (°)

C20A—C9A—C10A—C11A	159.65 (17)
C20A—C9A—C10A—C15A	−21.5 (3)
C20B—C9B—C10B—C11B	−140.01 (18)
C20B—C9B—C10B—C15B	43.2 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯O1B	0.86	2.02	2.821 (2)	155
C7A—H7AA⋯O1B	0.93	2.54	3.313 (2)	140
C12A—H12A⋯Cg1	0.93	2.75	3.632 (2)	159
N2B—H1NB⋯O1Ai	0.86	2.02	2.832 (2)	157
C7B—H7BA⋯O1Ai	0.93	2.47	3.256 (2)	143
C12B—H12B⋯Cg2i	0.93	2.65	3.462 (2)	146
C20A—H20B⋯N1Bii	0.96	2.57	3.504 (3)	164

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C1B–C6B and C1A–C6A rings, respectively.