(E)-2-[(2,4-Dichloro-phen-yl)imino-methyl]-6-methyl-phenol.

The title compound, C(14)H(11)Cl(2)NO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. There are two mol-ecules in the asymmetric unit. Head-to-tail π-π inter-actions [centroid-to-centroid distances of 3.682 (2), 3.708 (2), 3.904 (2) and 3.910 (2) Å] between adjacent mol-ecules produce two symmetry-independent infinite chains running along the b axis.

Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For Schiff base tautomerism, see: Şahin et al. (2005 ▶); Hadjoudis et al. (1987 ▶). For the structure of a similar compound, see: Karataş et al. (2005 ▶). For the classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H11Cl2NO

M = 280.14

Monoclinic,

a = 19.981 (2) Å

b = 7.1473 (6) Å

c = 20.057 (4) Å

β = 114.913 (11)°

V = 2597.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.45 × 0.21 × 0.11 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.903, T max = 0.953

30840 measured reflections

5370 independent reflections

3188 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 0.88

5370 reflections

334 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.40 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009684/ya2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009684/ya2087Isup2.hkl

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

C14H11Cl2NO	F(000) = 1152
Mr = 280.14	Dx = 1.433 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24378 reflections
a = 19.981 (2) Å	θ = 1.9–27.8°
b = 7.1473 (6) Å	µ = 0.48 mm−1
c = 20.057 (4) Å	T = 296 K
β = 114.913 (11)°	Prism, yellow
V = 2597.8 (7) Å3	0.45 × 0.21 × 0.11 mm
Z = 8

Stoe IPDSII diffractometer	5370 independent reflections
Radiation source: fine-focus sealed tube	3188 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.9°
ω scans	h = −25→25
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.903, Tmax = 0.953	l = −25→25
30840 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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0615P)2] where P = (Fo2 + 2Fc2)/3
S = 0.88	(Δ/σ)max = 0.002
5370 reflections	Δρmax = 0.40 e Å−3
334 parameters	Δρmin = −0.40 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (5)

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
C1A	0.03154 (13)	0.4396 (4)	0.67838 (15)	0.0634 (6)
C1B	0.81914 (17)	0.2780 (3)	0.96769 (12)	0.0640 (7)
C2A	0.05942 (13)	0.3951 (4)	0.62832 (13)	0.0621 (6)
H2A	0.0279	0.3652	0.5801	0.075*
C2B	0.74914 (17)	0.2265 (4)	0.92203 (13)	0.0683 (7)
H2B	0.7163	0.1896	0.9413	0.082*
C3A	0.13455 (12)	0.3954 (3)	0.65054 (11)	0.0527 (5)
C3B	0.72734 (15)	0.2291 (3)	0.84732 (12)	0.0620 (6)
H3B	0.6795	0.1937	0.8163	0.074*
C4A	0.18332 (11)	0.4388 (3)	0.72239 (11)	0.0475 (5)
C4B	0.77533 (13)	0.2836 (3)	0.81725 (11)	0.0508 (5)
C5A	0.15257 (13)	0.4858 (3)	0.77090 (12)	0.0573 (6)
H5A	0.1836	0.5182	0.8190	0.069*
C5B	0.84670 (13)	0.3341 (3)	0.86513 (11)	0.0537 (6)
C6A	0.07801 (14)	0.4855 (4)	0.74967 (14)	0.0651 (7)
H6A	0.0588	0.5162	0.7832	0.078*
C6B	0.86936 (15)	0.3331 (4)	0.94063 (11)	0.0620 (6)
H6B	0.9170	0.3684	0.9723	0.074*
C7A	0.30675 (12)	0.4072 (3)	0.80567 (11)	0.0482 (5)
H7A	0.2903	0.3737	0.8411	0.058*
C7B	0.69131 (13)	0.3133 (3)	0.69404 (11)	0.0518 (5)
H7B	0.6559	0.3458	0.7107	0.062*
C8A	0.38465 (11)	0.4160 (3)	0.82605 (10)	0.0463 (5)
C8B	0.67009 (12)	0.3030 (3)	0.61578 (11)	0.0487 (5)
C9A	0.41332 (12)	0.4551 (3)	0.77458 (10)	0.0471 (5)
C9B	0.72176 (12)	0.2636 (3)	0.58774 (10)	0.0482 (5)
C10A	0.48888 (12)	0.4609 (3)	0.79476 (12)	0.0562 (6)
C10B	0.70102 (14)	0.2580 (3)	0.51193 (12)	0.0579 (6)
C11A	0.53546 (13)	0.4309 (4)	0.86787 (14)	0.0659 (7)
H11A	0.5862	0.4369	0.8826	0.079*
C11B	0.62790 (16)	0.2882 (4)	0.46609 (12)	0.0696 (7)
H11B	0.6131	0.2834	0.4155	0.084*
C12A	0.50878 (14)	0.3922 (4)	0.91977 (13)	0.0710 (7)
H12A	0.5414	0.3723	0.9686	0.085*
C12B	0.57587 (15)	0.3253 (4)	0.49248 (13)	0.0733 (7)
H12B	0.5268	0.3445	0.4600	0.088*
C13A	0.43479 (13)	0.3833 (4)	0.89929 (11)	0.0607 (6)
H13A	0.4171	0.3552	0.9342	0.073*
C13B	0.59656 (13)	0.3339 (4)	0.56658 (13)	0.0629 (6)
H13B	0.5616	0.3605	0.5845	0.076*
C14A	0.51781 (15)	0.4976 (5)	0.73832 (16)	0.0848 (9)
H10A	0.5484	0.6073	0.7518	0.127*
H10B	0.4772	0.5167	0.6913	0.127*
H10C	0.5464	0.3923	0.7357	0.127*
C14B	0.75762 (17)	0.2210 (4)	0.48301 (14)	0.0827 (9)
H10D	0.7347	0.2258	0.4303	0.124*
H10E	0.7788	0.0994	0.4987	0.124*
H10F	0.7957	0.3141	0.5015	0.124*
N1A	0.25916 (9)	0.4438 (2)	0.74044 (9)	0.0467 (4)
N1B	0.75702 (11)	0.2794 (3)	0.74117 (9)	0.0504 (4)
O1A	0.36837 (9)	0.4854 (3)	0.70326 (8)	0.0620 (5)
H1A	0.3248 (10)	0.476 (4)	0.6980 (15)	0.083 (9)*
O1B	0.79332 (9)	0.2323 (3)	0.63215 (9)	0.0611 (4)
H1B	0.7955 (17)	0.240 (4)	0.6727 (11)	0.093 (10)*
Cl1A	−0.06295 (4)	0.43590 (12)	0.65100 (5)	0.0885 (3)
Cl1B	0.84855 (5)	0.26781 (11)	1.06241 (3)	0.0916 (3)
Cl2A	0.17044 (4)	0.33856 (12)	0.58800 (3)	0.0787 (2)
Cl2B	0.90870 (3)	0.40133 (11)	0.82999 (3)	0.0724 (2)

	U11	U22	U33	U12	U13	U23
C1A	0.0444 (13)	0.0550 (16)	0.0929 (18)	0.0012 (12)	0.0309 (13)	0.0058 (13)
C1B	0.102 (2)	0.0526 (15)	0.0446 (11)	0.0191 (15)	0.0379 (14)	0.0065 (11)
C2A	0.0472 (13)	0.0630 (17)	0.0672 (14)	−0.0081 (12)	0.0154 (11)	0.0032 (12)
C2B	0.098 (2)	0.0608 (17)	0.0586 (13)	0.0009 (15)	0.0457 (15)	0.0054 (12)
C3A	0.0484 (13)	0.0558 (14)	0.0540 (12)	−0.0056 (11)	0.0217 (10)	0.0024 (10)
C3B	0.0789 (17)	0.0586 (15)	0.0553 (12)	0.0000 (13)	0.0350 (13)	0.0058 (11)
C4A	0.0431 (11)	0.0440 (13)	0.0557 (12)	0.0006 (10)	0.0210 (10)	0.0038 (10)
C4B	0.0681 (15)	0.0443 (13)	0.0428 (10)	0.0102 (11)	0.0259 (11)	0.0030 (9)
C5A	0.0538 (14)	0.0601 (15)	0.0620 (13)	0.0029 (12)	0.0284 (11)	−0.0021 (11)
C5B	0.0669 (15)	0.0527 (14)	0.0456 (11)	0.0156 (12)	0.0279 (11)	0.0027 (10)
C6A	0.0586 (15)	0.0636 (17)	0.0840 (17)	0.0035 (13)	0.0407 (14)	−0.0023 (13)
C6B	0.0773 (17)	0.0599 (15)	0.0432 (11)	0.0171 (14)	0.0199 (11)	−0.0011 (10)
C7A	0.0519 (13)	0.0489 (14)	0.0484 (11)	−0.0002 (11)	0.0258 (10)	−0.0014 (9)
C7B	0.0592 (14)	0.0500 (14)	0.0518 (12)	0.0047 (11)	0.0289 (11)	0.0034 (10)
C8A	0.0452 (12)	0.0481 (13)	0.0428 (10)	0.0003 (10)	0.0158 (9)	−0.0047 (9)
C8B	0.0510 (13)	0.0481 (13)	0.0454 (10)	−0.0025 (11)	0.0188 (10)	0.0024 (9)
C9A	0.0450 (12)	0.0519 (14)	0.0423 (10)	−0.0005 (10)	0.0165 (9)	−0.0078 (9)
C9B	0.0488 (12)	0.0496 (13)	0.0435 (10)	−0.0090 (11)	0.0166 (10)	−0.0012 (9)
C10A	0.0468 (13)	0.0602 (16)	0.0618 (13)	−0.0023 (12)	0.0230 (11)	−0.0112 (11)
C10B	0.0729 (16)	0.0553 (15)	0.0465 (11)	−0.0142 (13)	0.0262 (11)	−0.0025 (10)
C11A	0.0419 (13)	0.0701 (18)	0.0743 (16)	0.0005 (12)	0.0134 (12)	−0.0159 (13)
C11B	0.0843 (19)	0.0688 (18)	0.0425 (11)	−0.0127 (15)	0.0139 (13)	0.0004 (11)
C12A	0.0587 (16)	0.083 (2)	0.0504 (13)	0.0082 (15)	0.0027 (12)	−0.0024 (12)
C12B	0.0631 (16)	0.0766 (19)	0.0566 (14)	0.0003 (15)	0.0020 (13)	0.0070 (13)
C13A	0.0575 (15)	0.0734 (17)	0.0441 (11)	0.0071 (13)	0.0145 (11)	0.0024 (11)
C13B	0.0550 (15)	0.0663 (17)	0.0640 (14)	0.0043 (13)	0.0217 (12)	0.0043 (12)
C14A	0.0615 (17)	0.115 (3)	0.0924 (19)	−0.0119 (17)	0.0470 (15)	−0.0137 (18)
C14B	0.098 (2)	0.103 (2)	0.0605 (14)	−0.0235 (19)	0.0466 (15)	−0.0126 (15)
N1A	0.0412 (9)	0.0507 (11)	0.0474 (9)	−0.0005 (9)	0.0179 (8)	−0.0015 (8)
N1B	0.0604 (12)	0.0514 (11)	0.0403 (8)	0.0030 (10)	0.0220 (9)	0.0018 (8)
O1A	0.0509 (10)	0.0930 (13)	0.0418 (8)	−0.0039 (9)	0.0190 (7)	0.0000 (8)
O1B	0.0493 (9)	0.0849 (13)	0.0507 (9)	−0.0049 (9)	0.0226 (8)	−0.0047 (8)
Cl1A	0.0454 (3)	0.0874 (6)	0.1318 (6)	−0.0008 (4)	0.0364 (4)	0.0067 (5)
Cl1B	0.1469 (7)	0.0863 (5)	0.0449 (3)	0.0213 (5)	0.0437 (4)	0.0063 (3)
Cl2A	0.0639 (4)	0.1209 (6)	0.0530 (3)	−0.0176 (4)	0.0263 (3)	−0.0127 (3)
Cl2B	0.0588 (4)	0.1028 (6)	0.0590 (3)	0.0109 (4)	0.0281 (3)	0.0000 (3)

C1A—C2A	1.375 (3)	C8A—C9A	1.404 (3)
C1A—C6A	1.377 (4)	C8A—C13A	1.406 (3)
C1A—Cl1A	1.730 (2)	C8B—C9B	1.397 (3)
C1B—C2B	1.361 (4)	C8B—C13B	1.400 (3)
C1B—C6B	1.384 (4)	C9A—O1A	1.348 (2)
C1B—Cl1B	1.738 (2)	C9A—C10A	1.389 (3)
C2A—C3A	1.374 (3)	C9B—O1B	1.347 (3)
C2A—H2A	0.9300	C9B—C10B	1.398 (3)
C2B—C3B	1.373 (3)	C10A—C11A	1.383 (3)
C2B—H2B	0.9300	C10A—C14A	1.495 (3)
C3A—C4A	1.393 (3)	C10B—C11B	1.377 (4)
C3A—Cl2A	1.735 (2)	C10B—C14B	1.496 (4)
C3B—C4B	1.387 (3)	C11A—C12A	1.383 (4)
C3B—H3B	0.9300	C11A—H11A	0.9300
C4A—C5A	1.393 (3)	C11B—C12B	1.377 (4)
C4A—N1A	1.402 (3)	C11B—H11B	0.9300
C4B—C5B	1.390 (3)	C12A—C13A	1.359 (3)
C4B—N1B	1.412 (2)	C12A—H12A	0.9300
C5A—C6A	1.366 (3)	C12B—C13B	1.366 (3)
C5A—H5A	0.9300	C12B—H12B	0.9300
C5B—C6B	1.386 (3)	C13A—H13A	0.9300
C5B—Cl2B	1.731 (2)	C13B—H13B	0.9300
C6A—H6A	0.9300	C14A—H10A	0.9600
C6B—H6B	0.9300	C14A—H10B	0.9600
C7A—N1A	1.279 (3)	C14A—H10C	0.9600
C7A—C8A	1.435 (3)	C14B—H10D	0.9600
C7A—H7A	0.9300	C14B—H10E	0.9600
C7B—N1B	1.277 (3)	C14B—H10F	0.9600
C7B—C8B	1.445 (3)	O1A—H1A	0.834 (17)
C7B—H7B	0.9300	O1B—H1B	0.798 (17)
C2A—C1A—C6A	120.7 (2)	C13B—C8B—C7B	119.9 (2)
C2A—C1A—Cl1A	119.2 (2)	O1A—C9A—C10A	117.44 (18)
C6A—C1A—Cl1A	120.1 (2)	O1A—C9A—C8A	121.10 (19)
C2B—C1B—C6B	121.5 (2)	C10A—C9A—C8A	121.45 (19)
C2B—C1B—Cl1B	120.2 (2)	O1B—C9B—C8B	121.73 (18)
C6B—C1B—Cl1B	118.3 (2)	O1B—C9B—C10B	117.4 (2)
C3A—C2A—C1A	119.1 (2)	C8B—C9B—C10B	120.9 (2)
C3A—C2A—H2A	120.5	C11A—C10A—C9A	117.9 (2)
C1A—C2A—H2A	120.5	C11A—C10A—C14A	121.9 (2)
C1B—C2B—C3B	119.6 (2)	C9A—C10A—C14A	120.3 (2)
C1B—C2B—H2B	120.2	C11B—C10B—C9B	117.8 (2)
C3B—C2B—H2B	120.2	C11B—C10B—C14B	122.1 (2)
C2A—C3A—C4A	121.9 (2)	C9B—C10B—C14B	120.0 (2)
C2A—C3A—Cl2A	119.54 (18)	C12A—C11A—C10A	121.9 (2)
C4A—C3A—Cl2A	118.56 (17)	C12A—C11A—H11A	119.0
C2B—C3B—C4B	121.3 (3)	C10A—C11A—H11A	119.0
C2B—C3B—H3B	119.4	C10B—C11B—C12B	122.3 (2)
C4B—C3B—H3B	119.4	C10B—C11B—H11B	118.9
C3A—C4A—C5A	117.0 (2)	C12B—C11B—H11B	118.9
C3A—C4A—N1A	118.80 (18)	C13A—C12A—C11A	119.8 (2)
C5A—C4A—N1A	124.06 (19)	C13A—C12A—H12A	120.1
C3B—C4B—C5B	117.95 (19)	C11A—C12A—H12A	120.1
C3B—C4B—N1B	123.5 (2)	C13B—C12B—C11B	119.7 (2)
C5B—C4B—N1B	118.40 (19)	C13B—C12B—H12B	120.1
C6A—C5A—C4A	121.7 (2)	C11B—C12B—H12B	120.1
C6A—C5A—H5A	119.1	C12A—C13A—C8A	120.9 (2)
C4A—C5A—H5A	119.1	C12A—C13A—H13A	119.5
C6B—C5B—C4B	121.4 (2)	C8A—C13A—H13A	119.5
C6B—C5B—Cl2B	119.1 (2)	C12B—C13B—C8B	120.4 (2)
C4B—C5B—Cl2B	119.51 (15)	C12B—C13B—H13B	119.8
C5A—C6A—C1A	119.6 (2)	C8B—C13B—H13B	119.8
C5A—C6A—H6A	120.2	C10A—C14A—H10A	109.5
C1A—C6A—H6A	120.2	C10A—C14A—H10B	109.5
C1B—C6B—C5B	118.2 (2)	H10A—C14A—H10B	109.5
C1B—C6B—H6B	120.9	C10A—C14A—H10C	109.5
C5B—C6B—H6B	120.9	H10A—C14A—H10C	109.5
N1A—C7A—C8A	122.16 (18)	H10B—C14A—H10C	109.5
N1A—C7A—H7A	118.9	C10B—C14B—H10D	109.5
C8A—C7A—H7A	118.9	C10B—C14B—H10E	109.5
N1B—C7B—C8B	122.3 (2)	H10D—C14B—H10E	109.5
N1B—C7B—H7B	118.9	C10B—C14B—H10F	109.5
C8B—C7B—H7B	118.9	H10D—C14B—H10F	109.5
C9A—C8A—C13A	118.0 (2)	H10E—C14B—H10F	109.5
C9A—C8A—C7A	121.95 (18)	C7A—N1A—C4A	121.04 (17)
C13A—C8A—C7A	120.03 (19)	C7B—N1B—C4B	120.91 (19)
C9B—C8B—C13B	118.83 (19)	C9A—O1A—H1A	108.4 (19)
C9B—C8B—C7B	121.29 (19)	C9B—O1B—H1B	104 (2)
C6A—C1A—C2A—C3A	0.6 (4)	C13A—C8A—C9A—C10A	0.2 (3)
Cl1A—C1A—C2A—C3A	−179.00 (19)	C7A—C8A—C9A—C10A	−179.2 (2)
C6B—C1B—C2B—C3B	−0.1 (4)	C13B—C8B—C9B—O1B	−179.9 (2)
Cl1B—C1B—C2B—C3B	−177.81 (19)	C7B—C8B—C9B—O1B	0.5 (3)
C1A—C2A—C3A—C4A	0.2 (4)	C13B—C8B—C9B—C10B	1.1 (3)
C1A—C2A—C3A—Cl2A	179.75 (19)	C7B—C8B—C9B—C10B	−178.5 (2)
C1B—C2B—C3B—C4B	−0.1 (4)	O1A—C9A—C10A—C11A	179.7 (2)
C2A—C3A—C4A—C5A	−1.2 (3)	C8A—C9A—C10A—C11A	−1.4 (3)
Cl2A—C3A—C4A—C5A	179.29 (18)	O1A—C9A—C10A—C14A	−0.7 (3)
C2A—C3A—C4A—N1A	−177.4 (2)	C8A—C9A—C10A—C14A	178.3 (2)
Cl2A—C3A—C4A—N1A	3.1 (3)	O1B—C9B—C10B—C11B	179.5 (2)
C2B—C3B—C4B—C5B	0.6 (3)	C8B—C9B—C10B—C11B	−1.5 (3)
C2B—C3B—C4B—N1B	176.5 (2)	O1B—C9B—C10B—C14B	−0.8 (3)
C3A—C4A—C5A—C6A	1.4 (4)	C8B—C9B—C10B—C14B	178.2 (2)
N1A—C4A—C5A—C6A	177.4 (2)	C9A—C10A—C11A—C12A	1.3 (4)
C3B—C4B—C5B—C6B	−0.9 (3)	C14A—C10A—C11A—C12A	−178.3 (3)
N1B—C4B—C5B—C6B	−177.1 (2)	C9B—C10B—C11B—C12B	0.8 (4)
C3B—C4B—C5B—Cl2B	179.49 (18)	C14B—C10B—C11B—C12B	−178.9 (3)
N1B—C4B—C5B—Cl2B	3.3 (3)	C10A—C11A—C12A—C13A	−0.1 (4)
C4A—C5A—C6A—C1A	−0.7 (4)	C10B—C11B—C12B—C13B	0.3 (4)
C2A—C1A—C6A—C5A	−0.4 (4)	C11A—C12A—C13A—C8A	−1.1 (4)
Cl1A—C1A—C6A—C5A	179.2 (2)	C9A—C8A—C13A—C12A	1.0 (4)
C2B—C1B—C6B—C5B	−0.2 (4)	C7A—C8A—C13A—C12A	−179.6 (2)
Cl1B—C1B—C6B—C5B	177.52 (18)	C11B—C12B—C13B—C8B	−0.8 (4)
C4B—C5B—C6B—C1B	0.7 (3)	C9B—C8B—C13B—C12B	0.1 (4)
Cl2B—C5B—C6B—C1B	−179.66 (18)	C7B—C8B—C13B—C12B	179.7 (2)
N1A—C7A—C8A—C9A	−3.7 (3)	C8A—C7A—N1A—C4A	−178.4 (2)
N1A—C7A—C8A—C13A	176.9 (2)	C3A—C4A—N1A—C7A	−151.4 (2)
N1B—C7B—C8B—C9B	−3.1 (4)	C5A—C4A—N1A—C7A	32.7 (3)
N1B—C7B—C8B—C13B	177.3 (2)	C8B—C7B—N1B—C4B	−177.5 (2)
C13A—C8A—C9A—O1A	179.1 (2)	C3B—C4B—N1B—C7B	34.1 (3)
C7A—C8A—C9A—O1A	−0.3 (3)	C5B—C4B—N1B—C7B	−150.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1A	0.83 (2)	1.86 (2)	2.603 (2)	149 (3)
O1B—H1B···N1B	0.80 (2)	1.86 (2)	2.599 (2)	155 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯N1A	0.834 (17)	1.86 (2)	2.603 (2)	149 (3)
O1B—H1B⋯N1B	0.798 (17)	1.86 (2)	2.599 (2)	155 (3)