Crystal structure of 1-[2-(2,6-di-chloro-phen-yl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol.

The central imidazole ring of the title compound, C24H20Cl2N2O, is twisted with respect to with the planes of the 2,6-di-chloro-benzene and two phenyl rings, making dihedral angles of 74.06 (18), 28.52 (17) and 67.65 (18)°, respectively. The phenyl ring not adjacent to the N-bonded 2-hy-droxy-propyl group shows the greatest twist, presumably to minimize steric inter-actions. In the crystal, mol-ecules are linked by O-H⋯N and C-H⋯O hydrogen-bond contacts into chains along the a-axis direction. The series of parallel chains form a two-dimensional sheet approximately parallel to the bc diagonal. In addition, C-H⋯π inter-actions are observed between the sheets. The atoms of the 2-hy-droxy-propyl group and the N atom of the 1H-imidazole ring to which it is bonded are disordered over two sets of sites, with an occupancy ratio of 0.722 (5):0.278 (5). The structure was refined as an inversion twin.

Related literature

For similar structures and background to the biological properties of imidazole derivatives, see: Mohamed et al. (2012 ▸, 2013a ▸,b ▸); Akkurt et al. (2013 ▸); Jasinski et al. (2015 ▸).

Experimental

Crystal data

C24H20Cl2N2O

M = 423.32

Orthorhombic,

a = 12.1468 (4) Å

b = 8.4194 (2) Å

c = 20.9636 (7) Å

V = 2143.92 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.86 mm−1

T = 173 K

0.48 × 0.44 × 0.26 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.541, T max = 1.000

16532 measured reflections

4076 independent reflections

3888 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.05

4076 reflections

278 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: refined as an inversion twin

Absolute structure parameter: 0.068 (18)

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006763/sj5450sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006763/sj5450Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006763/sj5450Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006763/sj5450fig1.tif

Perspective view of the title mol­ecule with 30% probability displacement ellipsoids. Only the major disorder component is shown.

Click here for additional data file.

b . DOI: 10.1107/S2056989015006763/sj5450fig2.tif

The mol­ecular packing of the title compound viewed along the b axis. H atoms not involved in the hydrogen bonding (dashed lines) have been omitted for clarity. Only the major disorder component is shown.

CCDC reference: 1057878

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H20Cl2N2O	F(000) = 880
Mr = 423.32	Dx = 1.311 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 7461 reflections
a = 12.1468 (4) Å	θ = 4.2–71.3°
b = 8.4194 (2) Å	µ = 2.86 mm−1
c = 20.9636 (7) Å	T = 173 K
V = 2143.92 (11) Å3	Irregular blocks, colourless
Z = 4	0.48 × 0.44 × 0.26 mm

Agilent Eos Gemini diffractometer	4076 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 16.0416 pixels mm-1	θmax = 71.5°, θmin = 4.2°
ω scans	h = −14→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −10→10
Tmin = 0.541, Tmax = 1.000	l = −25→25
16532 measured reflections

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.7142P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.26 e Å−3
4076 reflections	Δρmin = −0.18 e Å−3
278 parameters	Absolute structure: Refined as an inversion twin.
15 restraints	Absolute structure parameter: 0.068 (18)

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. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0230 (2)	0.8162 (4)	0.64803 (16)	0.0295 (6)
C2	−0.0445 (3)	0.8711 (4)	0.55579 (15)	0.0277 (6)
C3	0.0249 (2)	0.9942 (4)	0.57117 (15)	0.0268 (6)
C4A	0.141 (2)	1.064 (11)	0.667 (5)	0.030 (3)	0.278 (5)
H4A1	0.1256	1.0518	0.7132	0.036*	0.278 (5)
H4A2	0.1251	1.1758	0.6553	0.036*	0.278 (5)
C5A	0.2606 (16)	1.0292 (18)	0.6547 (8)	0.0314 (11)	0.278 (5)
H5A	0.2762	1.0391	0.6080	0.038*	0.278 (5)
C6A	0.3335 (15)	1.144 (3)	0.6916 (10)	0.057 (2)	0.278 (5)
H6A1	0.3217	1.2524	0.6758	0.086*	0.278 (5)
H6A2	0.4109	1.1148	0.6858	0.086*	0.278 (5)
H6A3	0.3148	1.1395	0.7370	0.086*	0.278 (5)
N1A	0.0677 (2)	0.9581 (3)	0.63059 (12)	0.0271 (5)	0.278 (5)
O1A	0.2788 (7)	0.8724 (11)	0.6741 (4)	0.0378 (7)	0.278 (5)
H1A	0.3136	0.8178	0.6509	0.057*	0.278 (5)
C4B	0.1417 (10)	1.055 (4)	0.6701 (19)	0.030 (3)	0.722 (5)
H4B1	0.1098	1.0639	0.7134	0.036*	0.722 (5)
H4B2	0.1450	1.1634	0.6518	0.036*	0.722 (5)
C5B	0.2591 (5)	0.9909 (7)	0.6759 (3)	0.0314 (11)	0.722 (5)
H5B	0.2570	0.8779	0.6905	0.038*	0.722 (5)
C6B	0.3226 (5)	1.0906 (10)	0.7239 (4)	0.057 (2)	0.722 (5)
H6B1	0.3215	1.2022	0.7105	0.086*	0.722 (5)
H6B2	0.3989	1.0533	0.7261	0.086*	0.722 (5)
H6B3	0.2882	1.0807	0.7660	0.086*	0.722 (5)
N1B	0.0677 (2)	0.9581 (3)	0.63059 (12)	0.0271 (5)	0.722 (5)
O1B	0.3065 (3)	0.9989 (4)	0.61501 (16)	0.0378 (7)	0.722 (5)
H1B	0.3568	0.9308	0.6120	0.057*	0.722 (5)
C7	0.0459 (3)	0.7343 (4)	0.70923 (16)	0.0314 (7)
C8	0.0008 (3)	0.7834 (4)	0.76676 (18)	0.0380 (7)
C9	0.0182 (3)	0.7043 (5)	0.82364 (19)	0.0491 (9)
H9	−0.0131	0.7426	0.8622	0.059*
C10	0.0821 (4)	0.5684 (5)	0.8233 (2)	0.0505 (10)
H10	0.0943	0.5120	0.8619	0.061*
C11	0.1281 (3)	0.5144 (4)	0.7672 (2)	0.0417 (8)
H11	0.1719	0.4210	0.7672	0.050*
C12	0.1104 (3)	0.5963 (4)	0.71118 (16)	0.0341 (7)
C13	−0.1113 (3)	0.8452 (3)	0.49796 (15)	0.0277 (6)
C14	−0.2071 (3)	0.7556 (4)	0.50122 (18)	0.0333 (7)
H14	−0.2307	0.7153	0.5413	0.040*
C15	−0.2688 (3)	0.7238 (4)	0.44710 (19)	0.0383 (8)
H15	−0.3336	0.6612	0.4505	0.046*
C16	−0.2374 (3)	0.7820 (5)	0.38861 (18)	0.0437 (8)
H16	−0.2798	0.7596	0.3516	0.052*
C17	−0.1426 (3)	0.8741 (5)	0.38446 (18)	0.0438 (9)
H17	−0.1207	0.9164	0.3444	0.053*
C18	−0.0797 (3)	0.9048 (4)	0.43837 (16)	0.0351 (7)
H18	−0.0146	0.9667	0.4348	0.042*
C19	0.0444 (3)	1.1482 (4)	0.53852 (15)	0.0287 (6)
C20	−0.0426 (3)	1.2530 (4)	0.53319 (17)	0.0352 (7)
H20	−0.1120	1.2261	0.5510	0.042*
C21	−0.0295 (3)	1.3975 (4)	0.50194 (19)	0.0428 (8)
H21	−0.0895	1.4694	0.4987	0.051*
C22	0.0711 (4)	1.4357 (4)	0.47581 (19)	0.0447 (9)
H22	0.0800	1.5338	0.4540	0.054*
C23	0.1579 (3)	1.3342 (5)	0.4809 (2)	0.0479 (10)
H23	0.2272	1.3625	0.4632	0.057*
C24	0.1457 (3)	1.1879 (4)	0.51228 (18)	0.0395 (8)
H24	0.2061	1.1167	0.5155	0.047*
N2	−0.0448 (2)	0.7612 (3)	0.60455 (13)	0.0300 (6)
Cl1	−0.08462 (8)	0.95060 (12)	0.76765 (5)	0.0517 (3)
Cl2	0.16981 (8)	0.52689 (10)	0.64134 (5)	0.0454 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0281 (15)	0.0269 (14)	0.0334 (15)	−0.0003 (11)	−0.0003 (13)	0.0026 (13)
C2	0.0268 (15)	0.0253 (14)	0.0310 (15)	0.0017 (11)	0.0014 (12)	0.0036 (12)
C3	0.0260 (15)	0.0231 (13)	0.0312 (15)	0.0015 (11)	0.0009 (12)	0.0017 (11)
C4A	0.0314 (17)	0.028 (4)	0.031 (4)	−0.0008 (14)	−0.0007 (14)	−0.005 (4)
C5A	0.037 (2)	0.030 (3)	0.027 (3)	0.003 (2)	−0.003 (3)	−0.004 (2)
C6A	0.037 (3)	0.078 (5)	0.056 (4)	0.011 (3)	−0.012 (3)	−0.034 (4)
N1A	0.0272 (13)	0.0249 (12)	0.0291 (14)	−0.0018 (10)	−0.0007 (10)	−0.0006 (9)
O1A	0.0399 (17)	0.0390 (18)	0.0345 (16)	0.0115 (13)	0.0053 (14)	0.0003 (13)
C4B	0.0314 (17)	0.028 (4)	0.031 (4)	−0.0008 (14)	−0.0007 (14)	−0.005 (4)
C5B	0.037 (2)	0.030 (3)	0.027 (3)	0.003 (2)	−0.003 (3)	−0.004 (2)
C6B	0.037 (3)	0.078 (5)	0.056 (4)	0.011 (3)	−0.012 (3)	−0.034 (4)
N1B	0.0272 (13)	0.0249 (12)	0.0291 (14)	−0.0018 (10)	−0.0007 (10)	−0.0006 (9)
O1B	0.0399 (17)	0.0390 (18)	0.0345 (16)	0.0115 (13)	0.0053 (14)	0.0003 (13)
C7	0.0302 (16)	0.0327 (16)	0.0313 (15)	−0.0045 (13)	−0.0005 (12)	0.0063 (13)
C8	0.0334 (17)	0.0409 (18)	0.0397 (17)	0.0031 (14)	0.0004 (15)	0.0058 (15)
C9	0.055 (2)	0.061 (2)	0.0318 (17)	0.004 (2)	0.0061 (17)	0.0057 (17)
C10	0.058 (2)	0.057 (2)	0.036 (2)	0.002 (2)	−0.0035 (17)	0.0211 (18)
C11	0.0415 (19)	0.0391 (18)	0.0446 (19)	0.0017 (15)	−0.0024 (17)	0.0121 (16)
C12	0.0340 (17)	0.0329 (16)	0.0355 (18)	−0.0038 (14)	0.0000 (14)	0.0046 (14)
C13	0.0290 (15)	0.0204 (13)	0.0339 (16)	0.0038 (11)	−0.0016 (12)	−0.0001 (12)
C14	0.0337 (17)	0.0268 (15)	0.0393 (17)	0.0011 (13)	−0.0016 (14)	0.0041 (13)
C15	0.0308 (16)	0.0301 (17)	0.054 (2)	−0.0025 (14)	−0.0097 (15)	0.0002 (15)
C16	0.047 (2)	0.0452 (19)	0.0389 (19)	0.0057 (16)	−0.0130 (16)	−0.0091 (15)
C17	0.048 (2)	0.053 (2)	0.0306 (18)	0.0016 (17)	−0.0005 (15)	−0.0008 (16)
C18	0.0340 (18)	0.0373 (17)	0.0339 (17)	0.0003 (14)	0.0011 (13)	0.0025 (14)
C19	0.0353 (17)	0.0216 (14)	0.0292 (15)	−0.0027 (12)	−0.0020 (12)	−0.0003 (12)
C20	0.0369 (18)	0.0308 (16)	0.0378 (17)	0.0030 (13)	0.0021 (15)	0.0044 (13)
C21	0.056 (2)	0.0255 (16)	0.047 (2)	0.0066 (15)	−0.0072 (17)	0.0030 (15)
C22	0.062 (3)	0.0271 (17)	0.045 (2)	−0.0137 (16)	−0.0128 (17)	0.0107 (15)
C23	0.041 (2)	0.050 (2)	0.053 (2)	−0.0220 (18)	−0.0037 (17)	0.0169 (18)
C24	0.0332 (18)	0.0364 (18)	0.049 (2)	−0.0033 (14)	−0.0011 (15)	0.0087 (16)
N2	0.0269 (13)	0.0278 (13)	0.0353 (14)	−0.0028 (10)	−0.0018 (11)	0.0046 (11)
Cl1	0.0463 (5)	0.0579 (5)	0.0509 (5)	0.0193 (4)	0.0084 (4)	0.0049 (4)
Cl2	0.0586 (5)	0.0359 (4)	0.0416 (4)	0.0092 (4)	0.0054 (4)	0.0020 (4)

C1—N2	1.313 (4)	C8—C9	1.382 (5)
C1—N1A	1.362 (4)	C8—Cl1	1.749 (4)
C1—C7	1.483 (4)	C9—C10	1.382 (6)
C2—C3	1.374 (4)	C9—H9	0.9500
C2—N2	1.379 (4)	C10—C11	1.378 (6)
C2—C13	1.475 (4)	C10—H10	0.9500
C3—N1A	1.384 (4)	C11—C12	1.379 (5)
C3—C19	1.485 (4)	C11—H11	0.9500
C4A—N1A	1.47 (3)	C12—Cl2	1.734 (4)
C4A—C5A	1.51 (3)	C13—C14	1.388 (5)
C4A—H4A1	0.9900	C13—C18	1.400 (5)
C4A—H4A2	0.9900	C14—C15	1.386 (5)
C5A—O1A	1.399 (15)	C14—H14	0.9500
C5A—C6A	1.52 (2)	C15—C16	1.374 (6)
C5A—H5A	1.0000	C15—H15	0.9500
C6A—H6A1	0.9800	C16—C17	1.391 (6)
C6A—H6A2	0.9800	C16—H16	0.9500
C6A—H6A3	0.9800	C17—C18	1.388 (5)
O1A—H1A	0.7924	C17—H17	0.9500
C4B—C5B	1.530 (17)	C18—H18	0.9500
C4B—H4B1	0.9900	C19—C20	1.381 (5)
C4B—H4B2	0.9900	C19—C24	1.388 (5)
C5B—O1B	1.401 (6)	C20—C21	1.391 (5)
C5B—C6B	1.521 (7)	C20—H20	0.9500
C5B—H5B	1.0000	C21—C22	1.377 (6)
C6B—H6B1	0.9800	C21—H21	0.9500
C6B—H6B2	0.9800	C22—C23	1.362 (6)
C6B—H6B3	0.9800	C22—H22	0.9500
O1B—H1B	0.8400	C23—C24	1.404 (5)
C7—C8	1.388 (5)	C23—H23	0.9500
C7—C12	1.402 (5)	C24—H24	0.9500
N2—C1—N1A	111.9 (3)	C9—C8—Cl1	118.0 (3)
N2—C1—C7	123.7 (3)	C7—C8—Cl1	118.9 (3)
N1A—C1—C7	124.4 (3)	C8—C9—C10	118.7 (4)
C3—C2—N2	109.5 (3)	C8—C9—H9	120.7
C3—C2—C13	130.0 (3)	C10—C9—H9	120.7
N2—C2—C13	120.5 (3)	C11—C10—C9	120.3 (3)
C2—C3—N1A	106.0 (3)	C11—C10—H10	119.8
C2—C3—C19	130.4 (3)	C9—C10—H10	119.8
N1A—C3—C19	123.2 (3)	C10—C11—C12	119.9 (3)
N1A—C4A—C5A	112 (2)	C10—C11—H11	120.1
N1A—C4A—H4A1	109.2	C12—C11—H11	120.1
C5A—C4A—H4A1	109.2	C11—C12—C7	121.8 (3)
N1A—C4A—H4A2	109.2	C11—C12—Cl2	119.1 (3)
C5A—C4A—H4A2	109.2	C7—C12—Cl2	119.2 (2)
H4A1—C4A—H4A2	107.9	C14—C13—C18	117.9 (3)
O1A—C5A—C4A	107 (5)	C14—C13—C2	120.1 (3)
O1A—C5A—C6A	111.1 (14)	C18—C13—C2	122.0 (3)
C4A—C5A—C6A	110.4 (17)	C15—C14—C13	121.2 (3)
O1A—C5A—H5A	109.6	C15—C14—H14	119.4
C4A—C5A—H5A	109.6	C13—C14—H14	119.4
C6A—C5A—H5A	109.6	C16—C15—C14	120.7 (3)
C5A—C6A—H6A1	109.5	C16—C15—H15	119.6
C5A—C6A—H6A2	109.5	C14—C15—H15	119.6
H6A1—C6A—H6A2	109.5	C15—C16—C17	119.0 (3)
C5A—C6A—H6A3	109.5	C15—C16—H16	120.5
H6A1—C6A—H6A3	109.5	C17—C16—H16	120.5
H6A2—C6A—H6A3	109.5	C18—C17—C16	120.6 (3)
C1—N1A—C3	106.5 (3)	C18—C17—H17	119.7
C1—N1A—C4A	129 (5)	C16—C17—H17	119.7
C3—N1A—C4A	124 (5)	C17—C18—C13	120.6 (3)
C5A—O1A—H1A	116.9	C17—C18—H18	119.7
C5B—C4B—H4B1	108.6	C13—C18—H18	119.7
C5B—C4B—H4B2	108.6	C20—C19—C24	119.5 (3)
H4B1—C4B—H4B2	107.6	C20—C19—C3	118.2 (3)
O1B—C5B—C6B	111.6 (5)	C24—C19—C3	122.3 (3)
O1B—C5B—C4B	107.1 (17)	C19—C20—C21	120.6 (3)
C6B—C5B—C4B	109.3 (6)	C19—C20—H20	119.7
O1B—C5B—H5B	109.6	C21—C20—H20	119.7
C6B—C5B—H5B	109.6	C22—C21—C20	119.6 (3)
C4B—C5B—H5B	109.6	C22—C21—H21	120.2
C5B—C6B—H6B1	109.5	C20—C21—H21	120.2
C5B—C6B—H6B2	109.5	C23—C22—C21	120.6 (3)
H6B1—C6B—H6B2	109.5	C23—C22—H22	119.7
C5B—C6B—H6B3	109.5	C21—C22—H22	119.7
H6B1—C6B—H6B3	109.5	C22—C23—C24	120.3 (4)
H6B2—C6B—H6B3	109.5	C22—C23—H23	119.8
C5B—O1B—H1B	109.5	C24—C23—H23	119.8
C8—C7—C12	116.2 (3)	C19—C24—C23	119.4 (3)
C8—C7—C1	122.6 (3)	C19—C24—H24	120.3
C12—C7—C1	121.0 (3)	C23—C24—H24	120.3
C9—C8—C7	123.1 (3)	C1—N2—C2	106.0 (3)
N2—C2—C3—N1A	0.0 (3)	C1—C7—C12—C11	−176.8 (3)
C13—C2—C3—N1A	−179.2 (3)	C8—C7—C12—Cl2	180.0 (3)
N2—C2—C3—C19	−172.4 (3)	C1—C7—C12—Cl2	3.4 (4)
C13—C2—C3—C19	8.4 (6)	C3—C2—C13—C14	−152.9 (3)
N1A—C4A—C5A—O1A	−61 (9)	N2—C2—C13—C14	28.0 (4)
N1A—C4A—C5A—C6A	178 (6)	C3—C2—C13—C18	28.9 (5)
N2—C1—N1A—C3	−0.4 (4)	N2—C2—C13—C18	−150.2 (3)
C7—C1—N1A—C3	−179.3 (3)	C18—C13—C14—C15	0.9 (5)
N2—C1—N1A—C4A	175.3 (18)	C2—C13—C14—C15	−177.3 (3)
C7—C1—N1A—C4A	−3.6 (19)	C13—C14—C15—C16	−0.7 (5)
C2—C3—N1A—C1	0.2 (3)	C14—C15—C16—C17	−0.3 (6)
C19—C3—N1A—C1	173.3 (3)	C15—C16—C17—C18	1.0 (6)
C2—C3—N1A—C4A	−175.8 (18)	C16—C17—C18—C13	−0.8 (6)
C19—C3—N1A—C4A	−2.7 (19)	C14—C13—C18—C17	−0.2 (5)
C5A—C4A—N1A—C1	92 (8)	C2—C13—C18—C17	178.0 (3)
C5A—C4A—N1A—C3	−93 (8)	C2—C3—C19—C20	62.2 (5)
N2—C1—C7—C8	−103.3 (4)	N1A—C3—C19—C20	−109.1 (4)
N1A—C1—C7—C8	75.4 (5)	C2—C3—C19—C24	−116.4 (4)
N2—C1—C7—C12	73.1 (4)	N1A—C3—C19—C24	72.3 (4)
N1A—C1—C7—C12	−108.2 (4)	C24—C19—C20—C21	−0.1 (5)
C12—C7—C8—C9	0.9 (5)	C3—C19—C20—C21	−178.7 (3)
C1—C7—C8—C9	177.4 (3)	C19—C20—C21—C22	0.4 (6)
C12—C7—C8—Cl1	−177.8 (3)	C20—C21—C22—C23	−0.8 (6)
C1—C7—C8—Cl1	−1.2 (5)	C21—C22—C23—C24	0.8 (6)
C7—C8—C9—C10	−1.1 (6)	C20—C19—C24—C23	0.2 (5)
Cl1—C8—C9—C10	177.6 (3)	C3—C19—C24—C23	178.7 (3)
C8—C9—C10—C11	0.6 (6)	C22—C23—C24—C19	−0.5 (6)
C9—C10—C11—C12	0.0 (6)	N1A—C1—N2—C2	0.4 (4)
C10—C11—C12—C7	−0.2 (6)	C7—C1—N2—C2	179.3 (3)
C10—C11—C12—Cl2	179.6 (3)	C3—C2—N2—C1	−0.2 (4)
C8—C7—C12—C11	−0.2 (5)	C13—C2—N2—C1	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···N2i	0.84	2.02	2.8468 (1)	170
C4B—H4B1···Cl1	0.99	2.79	3.5382 (1)	133
C14—H14···O1Bii	0.95	2.42	3.2107 (1)	141
C6B—H6B2···Cg3iii	0.98	2.78	3.6798 (1)	154

Table 1

Hydrogen-bond geometry (, )

Cg3 is the centroid of the C7C12 benzene ring.

DHA	DH	HA	D A	DHA
O1BH1BN2i	0.84	2.02	2.8468(1)	170
C14H14O1B ii	0.95	2.42	3.2107(1)	141
C6BH6B2Cg3iii	0.98	2.78	3.6798(1)	154

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