1-(2,5-Di­chloro­phenyl)-3-methyl-5-phenyl-1H-pyrazole

The title compound, C₁₆H₁₂Cl₂N₂, crystallizes in the centrosymmetric space group P2₁/c. Two independent but chemically identical mol­ecules comprise the asymmetric unit and in each of these the pyrazole ring is planar.

S1. Comment

Pyrazoles are one of the important classes of biologically active compounds. Pyrazole derivatives exhibit parasiticidal properties (Bristol-Meyers, 1973) and have been studied as potential antimalarial agents (Gein Stein et al., 1970). Pyrazolo[3,4-b]quinolines are known to exhibit bactericidal activity (Fraghaly et al., 1989). The present work was undertaken to explore the possible application of pyrazole analogues as antitubercular agents. In this respect, we have synthesized a series of pyrazoles and evaluated them for antitubercular activity against Mycobacterium tuberculosis H37R_v. The title compound, (I), was prepared by condensation of 2,5-dichlorophenylhydrazine with benzoylacetone in methanol in the presence of a catalytic amount of acetic acid. The structure of the product was confirmed by NMR spectroscopy. To confirm further the position of attachment of the methyl and phenyl groups on the pyrazole ring, and to obtain more detailed structural information on the conformation of the molecule in the crystalline state, its X-ray structure determination has been carried out and the results are presented here. \sch

The crystal of (I) contains two molecules (A and B) in the asymmetric unit. Fig. 1 shows a displacement ellipsoid plot of the labelled asymmetric unit, and selected geometric parameters are presented in Table 1. A pairwise comparison between these two molecules shows no significant differences in bond lengths or angles. Pairwise comparisons of torsion angles, however, do show some differences between the molecules: C9A—N1A—C1A—C2A and N1A—C9A—C10A—C15A are −67.9 (2) and −45.2 (2)°, respectively, while C9B—N1B—C1B—C2B and N1B—C9B—C10B—C15B are −79.6 (2) and −37.6 (3)°, respectively.

The pyrazole moiety in both molecules is nearly planar, with overall root-mean square deviations (r.m.s.d.) for the ring atoms of 0.005 (1) Å for either molecule. It has been reported (Krishna et al., 1999) that the N—N bond length in the pyrazoline ring varies over a wide range, from 1.234 (8) to 1.385 (4) Å, where the length depends on the substituents bonded to the N atoms. Accordingly, the length of the adjacent C═N bond ranges from 1.288 (4) to 1.461 (8) Å. These differences are caused by a varying degree of conjugation in the π-electron portion of the pyrazoline ring, which is sensitive to the nature of the substituent(s) bonded to the atoms of the π system. The N1—N2 bond length of 1.3674 (19) Å found in (I) further extends this range, approximating the length of a pure single bond (1.41 Å; Burke-Laing & Laing, 1976). There is an extended conjugation between the π-electron system of the pyrazole ring and the phenyl group, which is evident from the bond lengths N2═C7, C7—C8, C8═C9 and C9—C10.

The mode of packing of (I) along the c direction is illustrated in Fig. 2. In addition to weak C—H···π interactions, van der Waals forces contribute to the stabilization of the crystal structure.

In Table 2, Cg1 is the centroid of ring N1A/N2A/C7A/C8A/C9A and Cg2 is the centroid of ring C10B/C11B/C12B/C13B/C14B/C15B.

S2. Experimental

A mixture of 2,5-dichlorophenylhydrazine (0.354 g, 2 mmol) and benzoylacetone (0.324 g, 2 mmol) was dissolved in methanol (10 ml). To this reaction mixture were added 2 drops of acetic acid and the solution was refluxed for 5 h. After completion of the reaction, the solvent was removed and the resultant solid was crystallized from methanol to afford colourless crystals of (I) suitable for X-ray analysis. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m.): 2.39 (s, 3H), 6.36 (s, 1H), 7.17–7.20(m, 2H), 7.26–7.29 (m, 3H), 7.32 (t, 2H), 7.49 (q, 1H); ¹³C NMR (CDCl₃, δ, p.p.m.): 14.0, 106.7, 127.8, 128.5, 128.6, 130.1,130.2, 130.3, 130.7, 131.2, 133.1, 139.2, 145.8, 150.5.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELX97 and local procedures.

Figures

	Fig. 1. A view of the two independent molecules, A and B, of the asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The crystal packing of (I), viewed along the c axis. H atoms have been omitted for clarity.

1-(2,5-Dichlorophenyl)-3-methyl-5-phenyl-1H-pyrazole

Crystal data

C16H12Cl2N2	F(000) = 1248
Mr = 303.18	Dx = 1.415 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6703 reflections
a = 17.3805 (3) Å	θ = 1.0–27.5°
b = 14.8094 (2) Å	µ = 0.45 mm^−1
c = 11.0596 (2) Å	T = 90 K
β = 90.7798 (6)°	Block, colourless
V = 2846.42 (8) Å^3	0.35 × 0.30 × 0.20 mm
Z = 8

Data collection

Nonius KappaCCD area-detector diffractometer	6525 independent reflections
Radiation source: fine-focus sealed tube	5003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 1.8°
ω scans at fixed χ = 55°	h = −22→22
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −19→19
Tmin = 0.860, Tmax = 0.916	l = −14→14
12695 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.7814P] where P = (Fo^2 + 2Fc^2)/3
6525 reflections	(Δ/σ)max = 0.023
363 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1A	0.71772 (2)	0.53228 (3)	1.01650 (4)	0.02567 (12)
Cl2A	0.92616 (2)	0.44584 (3)	0.57817 (4)	0.02186 (11)
N1A	0.87453 (8)	0.44677 (9)	1.03205 (12)	0.0137 (3)
N2A	0.87236 (8)	0.35850 (9)	1.06812 (12)	0.0154 (3)
C1A	0.84813 (9)	0.47009 (11)	0.91341 (14)	0.0142 (3)
C2A	0.77733 (9)	0.51242 (12)	0.89532 (15)	0.0168 (4)
C3A	0.75376 (10)	0.53754 (12)	0.77965 (15)	0.0193 (4)
H3A	0.7061	0.5680	0.7677	0.023*
C4A	0.79978 (10)	0.51813 (11)	0.68176 (15)	0.0174 (4)
H4A	0.7842	0.5356	0.6025	0.021*
C5A	0.86878 (9)	0.47295 (11)	0.70059 (14)	0.0157 (4)
C6A	0.89382 (9)	0.44930 (11)	0.81590 (14)	0.0145 (3)
H6A	0.9416	0.4193	0.8277	0.017*
C7A	0.89462 (9)	0.36065 (12)	1.18418 (15)	0.0158 (4)
C8A	0.90990 (9)	0.44938 (11)	1.22229 (15)	0.0160 (4)
H8A	0.9265	0.4680	1.3006	0.019*
C9A	0.89597 (9)	0.50390 (11)	1.12380 (14)	0.0138 (3)
C10A	0.90110 (9)	0.60254 (11)	1.10936 (15)	0.0153 (4)
C11A	0.87167 (10)	0.65860 (12)	1.19976 (15)	0.0182 (4)
H11A	0.8485	0.6326	1.2688	0.022*
C12A	0.87612 (10)	0.75151 (12)	1.18915 (16)	0.0215 (4)
H12A	0.8556	0.7890	1.2505	0.026*
C13A	0.91047 (10)	0.79011 (12)	1.08899 (16)	0.0212 (4)
H13A	0.9131	0.8539	1.0816	0.025*
C14A	0.94082 (10)	0.73544 (12)	0.99997 (16)	0.0193 (4)
H14A	0.9649	0.7619	0.9320	0.023*
C15A	0.93618 (9)	0.64225 (12)	1.00977 (15)	0.0170 (4)
H15A	0.9570	0.6052	0.9483	0.020*
C16A	0.89976 (10)	0.27504 (12)	1.25520 (16)	0.0211 (4)
H16A	0.8646	0.2302	1.2199	0.032*
H16B	0.8855	0.2868	1.3392	0.032*
H16C	0.9526	0.2519	1.2531	0.032*
Cl1B	0.57659 (3)	0.26629 (3)	0.81813 (4)	0.02524 (12)
Cl2B	0.75106 (2)	0.41782 (3)	0.37447 (4)	0.02083 (11)
N1B	0.54446 (8)	0.44421 (9)	0.69696 (12)	0.0153 (3)
N2B	0.56845 (8)	0.50777 (10)	0.77941 (12)	0.0181 (3)
C1B	0.60265 (9)	0.38969 (11)	0.64284 (14)	0.0148 (3)
C2B	0.62370 (9)	0.30691 (12)	0.69258 (15)	0.0175 (4)
C3B	0.68325 (10)	0.25756 (12)	0.64287 (16)	0.0210 (4)
H3B	0.6971	0.2008	0.6766	0.025*
C4B	0.72266 (10)	0.29064 (12)	0.54425 (15)	0.0198 (4)
H4B	0.7636	0.2571	0.5100	0.024*
C5B	0.70117 (9)	0.37362 (12)	0.49646 (14)	0.0159 (4)
C6B	0.64193 (9)	0.42320 (12)	0.54480 (15)	0.0159 (4)
H6B	0.6282	0.4800	0.5109	0.019*
C7B	0.50387 (10)	0.54259 (11)	0.82317 (15)	0.0177 (4)
C8B	0.43901 (10)	0.50147 (12)	0.77012 (15)	0.0178 (4)
H8B	0.3867	0.5149	0.7861	0.021*
C9B	0.46593 (9)	0.43790 (11)	0.69046 (15)	0.0159 (4)
C10B	0.42184 (9)	0.37738 (11)	0.61003 (15)	0.0159 (4)
C11B	0.35116 (10)	0.34483 (12)	0.64968 (16)	0.0214 (4)
H11B	0.3355	0.3570	0.7300	0.026*
C12B	0.30357 (10)	0.29495 (13)	0.57359 (17)	0.0255 (4)
H12B	0.2557	0.2731	0.6019	0.031*
C13B	0.32573 (10)	0.27692 (13)	0.45610 (17)	0.0239 (4)
H13B	0.2928	0.2433	0.4036	0.029*
C14B	0.39586 (10)	0.30796 (12)	0.41559 (16)	0.0202 (4)
H14B	0.4113	0.2950	0.3354	0.024*
C15B	0.44385 (10)	0.35802 (11)	0.49154 (15)	0.0174 (4)
H15B	0.4919	0.3792	0.4629	0.021*
C16B	0.50760 (11)	0.61498 (13)	0.91728 (16)	0.0230 (4)
H16D	0.5580	0.6134	0.9580	0.034*
H16E	0.4671	0.6050	0.9767	0.034*
H16F	0.5001	0.6740	0.8788	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0178 (2)	0.0395 (3)	0.0198 (2)	0.00419 (19)	0.00437 (17)	−0.00346 (19)
Cl2A	0.0249 (2)	0.0270 (3)	0.0137 (2)	0.00008 (18)	0.00391 (17)	−0.00172 (17)
N1A	0.0170 (7)	0.0121 (7)	0.0121 (7)	−0.0007 (6)	0.0002 (5)	0.0002 (5)
N2A	0.0167 (7)	0.0121 (7)	0.0175 (7)	−0.0015 (6)	0.0023 (6)	0.0020 (6)
C1A	0.0177 (8)	0.0121 (8)	0.0127 (8)	−0.0046 (7)	−0.0017 (6)	−0.0005 (6)
C2A	0.0157 (8)	0.0194 (9)	0.0154 (8)	−0.0026 (7)	0.0026 (7)	−0.0022 (7)
C3A	0.0154 (9)	0.0210 (9)	0.0214 (9)	−0.0003 (7)	−0.0035 (7)	−0.0001 (7)
C4A	0.0190 (9)	0.0174 (9)	0.0158 (8)	−0.0037 (7)	−0.0033 (7)	0.0014 (7)
C5A	0.0183 (9)	0.0154 (9)	0.0133 (8)	−0.0047 (7)	0.0025 (7)	−0.0019 (7)
C6A	0.0154 (8)	0.0113 (8)	0.0168 (8)	−0.0017 (7)	−0.0010 (7)	−0.0015 (7)
C7A	0.0136 (8)	0.0174 (9)	0.0165 (8)	0.0001 (7)	0.0044 (7)	0.0007 (7)
C8A	0.0166 (8)	0.0185 (9)	0.0129 (8)	−0.0008 (7)	0.0018 (7)	0.0001 (7)
C9A	0.0129 (8)	0.0151 (9)	0.0135 (8)	−0.0004 (6)	0.0025 (6)	−0.0013 (7)
C10A	0.0142 (8)	0.0158 (9)	0.0158 (8)	−0.0008 (7)	−0.0024 (7)	−0.0004 (7)
C11A	0.0187 (9)	0.0212 (10)	0.0146 (8)	−0.0016 (7)	0.0013 (7)	−0.0020 (7)
C12A	0.0226 (9)	0.0201 (10)	0.0217 (9)	0.0035 (7)	0.0016 (7)	−0.0060 (7)
C13A	0.0236 (9)	0.0129 (9)	0.0272 (10)	0.0003 (7)	−0.0026 (8)	−0.0007 (7)
C14A	0.0213 (9)	0.0189 (9)	0.0177 (9)	−0.0020 (7)	0.0002 (7)	0.0019 (7)
C15A	0.0176 (9)	0.0181 (9)	0.0153 (8)	0.0000 (7)	−0.0003 (7)	−0.0027 (7)
C16A	0.0239 (9)	0.0187 (9)	0.0208 (9)	0.0011 (7)	0.0011 (7)	0.0047 (7)
Cl1B	0.0283 (2)	0.0262 (3)	0.0214 (2)	0.00247 (19)	0.00524 (18)	0.00758 (19)
Cl2B	0.0186 (2)	0.0256 (2)	0.0184 (2)	0.00023 (17)	0.00494 (17)	−0.00070 (17)
N1B	0.0142 (7)	0.0172 (8)	0.0146 (7)	0.0011 (6)	0.0011 (6)	−0.0017 (6)
N2B	0.0217 (8)	0.0174 (8)	0.0151 (7)	0.0000 (6)	0.0006 (6)	−0.0036 (6)
C1B	0.0118 (8)	0.0167 (9)	0.0159 (8)	0.0010 (7)	−0.0010 (6)	−0.0044 (7)
C2B	0.0161 (9)	0.0202 (9)	0.0163 (9)	−0.0016 (7)	0.0007 (7)	0.0008 (7)
C3B	0.0220 (9)	0.0181 (9)	0.0230 (10)	0.0058 (7)	−0.0006 (7)	0.0023 (7)
C4B	0.0165 (9)	0.0215 (10)	0.0212 (9)	0.0052 (7)	0.0000 (7)	−0.0038 (7)
C5B	0.0140 (8)	0.0198 (9)	0.0140 (8)	−0.0012 (7)	0.0008 (6)	−0.0026 (7)
C6B	0.0151 (8)	0.0152 (9)	0.0175 (9)	0.0013 (7)	−0.0018 (7)	−0.0008 (7)
C7B	0.0225 (9)	0.0173 (9)	0.0133 (8)	0.0036 (7)	0.0019 (7)	0.0009 (7)
C8B	0.0165 (8)	0.0209 (9)	0.0160 (9)	0.0032 (7)	0.0035 (7)	0.0020 (7)
C9B	0.0156 (8)	0.0169 (9)	0.0152 (8)	0.0009 (7)	0.0017 (7)	0.0034 (7)
C10B	0.0155 (8)	0.0135 (9)	0.0185 (9)	0.0035 (7)	−0.0015 (7)	0.0020 (7)
C11B	0.0202 (9)	0.0230 (10)	0.0211 (9)	0.0001 (7)	0.0033 (7)	0.0009 (8)
C12B	0.0166 (9)	0.0289 (11)	0.0312 (11)	−0.0046 (8)	0.0048 (8)	0.0001 (8)
C13B	0.0198 (9)	0.0231 (10)	0.0286 (10)	−0.0016 (8)	−0.0033 (8)	−0.0058 (8)
C14B	0.0220 (9)	0.0204 (10)	0.0182 (9)	0.0031 (7)	−0.0004 (7)	−0.0038 (7)
C15B	0.0167 (9)	0.0165 (9)	0.0188 (9)	0.0027 (7)	0.0014 (7)	0.0015 (7)
C16B	0.0255 (10)	0.0246 (10)	0.0189 (9)	0.0045 (8)	0.0002 (7)	−0.0047 (8)

Geometric parameters (Å, º)

Cl1A—C2A	1.7303 (17)	Cl1B—C2B	1.7295 (17)
Cl2A—C5A	1.7394 (17)	Cl2B—C5B	1.7413 (17)
N1A—N2A	1.3674 (19)	N1B—C9B	1.369 (2)
N1A—C9A	1.369 (2)	N1B—N2B	1.3716 (19)
N1A—C1A	1.426 (2)	N1B—C1B	1.432 (2)
N2A—C7A	1.336 (2)	N2B—C7B	1.332 (2)
C1A—C6A	1.383 (2)	C1B—C6B	1.381 (2)
C1A—C2A	1.393 (2)	C1B—C2B	1.391 (2)
C2A—C3A	1.389 (2)	C2B—C3B	1.387 (2)
C3A—C4A	1.385 (2)	C3B—C4B	1.385 (2)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.387 (2)	C4B—C5B	1.387 (2)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.387 (2)	C5B—C6B	1.378 (2)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.404 (2)	C7B—C8B	1.403 (2)
C7A—C16A	1.493 (2)	C7B—C16B	1.495 (2)
C8A—C9A	1.375 (2)	C8B—C9B	1.376 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.472 (2)	C9B—C10B	1.471 (2)
C10A—C15A	1.396 (2)	C10B—C11B	1.396 (2)
C10A—C11A	1.402 (2)	C10B—C15B	1.400 (2)
C11A—C12A	1.383 (2)	C11B—C12B	1.385 (2)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.389 (2)	C12B—C13B	1.386 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.385 (2)	C13B—C14B	1.383 (2)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.387 (2)	C14B—C15B	1.390 (2)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16B	0.9800	C16B—H16E	0.9800
C16A—H16C	0.9800	C16B—H16F	0.9800
N2A—N1A—C9A	112.51 (13)	C9B—N1B—N2B	112.06 (13)
N2A—N1A—C1A	119.34 (13)	N2B—N1B—C1B	117.06 (13)
C9A—N1A—C1A	127.81 (14)	C9B—N1B—C1B	130.47 (14)
C7A—N2A—N1A	104.40 (13)	C7B—N2B—N1B	104.90 (13)
C6A—C1A—C2A	120.25 (15)	C6B—C1B—C2B	119.80 (15)
C6A—C1A—N1A	118.85 (14)	C6B—C1B—N1B	119.02 (15)
C2A—C1A—N1A	120.89 (15)	C2B—C1B—N1B	121.02 (15)
C3A—C2A—C1A	120.11 (16)	C3B—C2B—C1B	120.10 (16)
C3A—C2A—Cl1A	119.72 (13)	C3B—C2B—Cl1B	119.94 (14)
C1A—C2A—Cl1A	120.16 (13)	C1B—C2B—Cl1B	119.95 (13)
C4A—C3A—C2A	119.89 (16)	C4B—C3B—C2B	120.37 (16)
C4A—C3A—H3A	120.1	C4B—C3B—H3B	119.8
C2A—C3A—H3A	120.1	C2B—C3B—H3B	119.8
C3A—C4A—C5A	119.36 (15)	C3B—C4B—C5B	118.68 (16)
C3A—C4A—H4A	120.3	C3B—C4B—H4B	120.7
C5A—C4A—H4A	120.3	C5B—C4B—H4B	120.7
C6A—C5A—C4A	121.33 (15)	C6B—C5B—C4B	121.52 (16)
C6A—C5A—Cl2A	118.78 (13)	C6B—C5B—Cl2B	118.86 (13)
C4A—C5A—Cl2A	119.89 (13)	C4B—C5B—Cl2B	119.61 (13)
C1A—C6A—C5A	118.98 (15)	C5B—C6B—C1B	119.53 (16)
C1A—C6A—H6A	120.5	C5B—C6B—H6B	120.2
C5A—C6A—H6A	120.5	C1B—C6B—H6B	120.2
N2A—C7A—C8A	111.21 (15)	N2B—C7B—C8B	110.87 (15)
N2A—C7A—C16A	119.97 (15)	N2B—C7B—C16B	120.11 (15)
C8A—C7A—C16A	128.82 (15)	C8B—C7B—C16B	129.01 (16)
C9A—C8A—C7A	106.34 (15)	C9B—C8B—C7B	106.66 (15)
C9A—C8A—H8A	126.8	C9B—C8B—H8B	126.7
C7A—C8A—H8A	126.8	C7B—C8B—H8B	126.7
N1A—C9A—C8A	105.52 (14)	N1B—C9B—C8B	105.50 (15)
N1A—C9A—C10A	123.30 (14)	N1B—C9B—C10B	125.74 (15)
C8A—C9A—C10A	131.18 (15)	C8B—C9B—C10B	128.71 (15)
C15A—C10A—C11A	118.73 (15)	C11B—C10B—C15B	118.44 (15)
C15A—C10A—C9A	122.09 (15)	C11B—C10B—C9B	118.29 (15)
C11A—C10A—C9A	119.15 (15)	C15B—C10B—C9B	122.98 (15)
C12A—C11A—C10A	120.49 (16)	C12B—C11B—C10B	120.93 (17)
C12A—C11A—H11A	119.8	C12B—C11B—H11B	119.5
C10A—C11A—H11A	119.8	C10B—C11B—H11B	119.5
C11A—C12A—C13A	120.15 (16)	C11B—C12B—C13B	120.06 (17)
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.0
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.0
C14A—C13A—C12A	119.91 (16)	C14B—C13B—C12B	119.80 (17)
C14A—C13A—H13A	120.0	C14B—C13B—H13B	120.1
C12A—C13A—H13A	120.0	C12B—C13B—H13B	120.1
C13A—C14A—C15A	120.21 (16)	C13B—C14B—C15B	120.39 (17)
C13A—C14A—H14A	119.9	C13B—C14B—H14B	119.8
C15A—C14A—H14A	119.9	C15B—C14B—H14B	119.8
C14A—C15A—C10A	120.49 (16)	C14B—C15B—C10B	120.38 (16)
C14A—C15A—H15A	119.8	C14B—C15B—H15B	119.8
C10A—C15A—H15A	119.8	C10B—C15B—H15B	119.8
C7A—C16A—H16A	109.5	C7B—C16B—H16D	109.5
C7A—C16A—H16B	109.5	C7B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C7A—C16A—H16C	109.5	C7B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C9A—N1A—N2A—C7A	−1.36 (17)	C9B—N1B—N2B—C7B	−1.10 (18)
C1A—N1A—N2A—C7A	−175.21 (14)	C1B—N1B—N2B—C7B	−174.56 (14)
N2A—N1A—C1A—C6A	−74.55 (19)	C9B—N1B—C1B—C6B	104.9 (2)
C9A—N1A—C1A—C6A	112.65 (19)	N2B—N1B—C1B—C6B	−83.03 (18)
N2A—N1A—C1A—C2A	104.93 (18)	C9B—N1B—C1B—C2B	−79.6 (2)
C9A—N1A—C1A—C2A	−67.9 (2)	N2B—N1B—C1B—C2B	92.37 (19)
C6A—C1A—C2A—C3A	−2.8 (2)	C6B—C1B—C2B—C3B	−0.9 (2)
N1A—C1A—C2A—C3A	177.71 (15)	N1B—C1B—C2B—C3B	−176.26 (15)
C6A—C1A—C2A—Cl1A	176.13 (13)	C6B—C1B—C2B—Cl1B	178.04 (12)
N1A—C1A—C2A—Cl1A	−3.3 (2)	N1B—C1B—C2B—Cl1B	2.7 (2)
C1A—C2A—C3A—C4A	1.8 (3)	C1B—C2B—C3B—C4B	0.6 (3)
Cl1A—C2A—C3A—C4A	−177.12 (13)	Cl1B—C2B—C3B—C4B	−178.31 (13)
C2A—C3A—C4A—C5A	0.6 (3)	C2B—C3B—C4B—C5B	−0.2 (3)
C3A—C4A—C5A—C6A	−2.1 (3)	C3B—C4B—C5B—C6B	0.0 (2)
C3A—C4A—C5A—Cl2A	178.55 (13)	C3B—C4B—C5B—Cl2B	178.68 (13)
C2A—C1A—C6A—C5A	1.3 (2)	C4B—C5B—C6B—C1B	−0.2 (2)
N1A—C1A—C6A—C5A	−179.17 (14)	Cl2B—C5B—C6B—C1B	−178.95 (12)
C4A—C5A—C6A—C1A	1.1 (2)	C2B—C1B—C6B—C5B	0.7 (2)
Cl2A—C5A—C6A—C1A	−179.51 (12)	N1B—C1B—C6B—C5B	176.16 (14)
N1A—N2A—C7A—C8A	0.74 (18)	N1B—N2B—C7B—C8B	0.42 (18)
N1A—N2A—C7A—C16A	−179.71 (14)	N1B—N2B—C7B—C16B	179.77 (15)
N2A—C7A—C8A—C9A	0.10 (19)	N2B—C7B—C8B—C9B	0.4 (2)
C16A—C7A—C8A—C9A	−179.40 (16)	C16B—C7B—C8B—C9B	−178.90 (17)
N2A—N1A—C9A—C8A	1.44 (18)	N2B—N1B—C9B—C8B	1.34 (19)
C1A—N1A—C9A—C8A	174.65 (15)	C1B—N1B—C9B—C8B	173.68 (16)
N2A—N1A—C9A—C10A	−178.60 (14)	N2B—N1B—C9B—C10B	179.09 (15)
C1A—N1A—C9A—C10A	−5.4 (3)	C1B—N1B—C9B—C10B	−8.6 (3)
C7A—C8A—C9A—N1A	−0.90 (18)	C7B—C8B—C9B—N1B	−1.01 (18)
C7A—C8A—C9A—C10A	179.15 (16)	C7B—C8B—C9B—C10B	−178.67 (16)
N1A—C9A—C10A—C15A	−45.2 (2)	N1B—C9B—C10B—C11B	148.79 (17)
C8A—C9A—C10A—C15A	134.72 (19)	C8B—C9B—C10B—C11B	−34.0 (3)
N1A—C9A—C10A—C11A	136.45 (16)	N1B—C9B—C10B—C15B	−37.6 (3)
C8A—C9A—C10A—C11A	−43.6 (3)	C8B—C9B—C10B—C15B	139.66 (19)
C15A—C10A—C11A—C12A	1.2 (2)	C15B—C10B—C11B—C12B	−0.4 (3)
C9A—C10A—C11A—C12A	179.55 (15)	C9B—C10B—C11B—C12B	173.58 (16)
C10A—C11A—C12A—C13A	−0.5 (3)	C10B—C11B—C12B—C13B	−0.2 (3)
C11A—C12A—C13A—C14A	−0.5 (3)	C11B—C12B—C13B—C14B	0.8 (3)
C12A—C13A—C14A—C15A	0.8 (3)	C12B—C13B—C14B—C15B	−0.8 (3)
C13A—C14A—C15A—C10A	−0.1 (2)	C13B—C14B—C15B—C10B	0.2 (3)
C11A—C10A—C15A—C14A	−0.8 (2)	C11B—C10B—C15B—C14B	0.4 (2)
C9A—C10A—C15A—C14A	−179.17 (15)	C9B—C10B—C15B—C14B	−173.27 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···N2B	0.95	2.56	3.251 (2)	130
C13A—H13A···Cl2A^i	0.95	2.97	3.9219 (18)	176
C15A—H15A···C1AG^ii	0.95	2.84	3.5387 (17)	132
C3B—H3B···Cl2B^iii	0.95	2.95	3.8228 (18)	154
C4B—H4B···N2A^iv	0.95	2.62	3.420 (2)	142
C6B—H6B···C3BG^v	0.95	2.90	3.8110 (17)	160
C8B—H8B···Cl1A^vi	0.95	2.94	3.6625 (18)	134
C16B—H16F···Cl1B^vii	0.98	2.88	3.7199 (19)	144

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, −y+1, −z+2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y+1, −z+2; (vii) −x+1, y+1/2, −z+3/2.