2,6-Dichloro-N-phenyl­benzamide

Liu, H.; Xu, N.; Yang, B.; Wang, W.; Han, P.

doi:10.1107/S1600536811019222

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1738

doi:10.1107/S1600536811019222

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2,6-Dichloro-N-phenylbenzamide

Hui Liu,^a Ning Xu,^b Bo Yang,^a Wei Wang ^a and Ping-fang Han ^a ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Environment, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: hpf@njut.com

(Received 28 April 2011; accepted 20 May 2011; online 18 June 2011)

There are two independent molecules in the asymmetric unit of the title compound, C₁₃H₉Cl₂NO, in which the dihedral angles between the phenyl and dichlorophenyl rings have significantly different values [48.5 (3) and 65.1 (3)°]. In the crystal, the molecules are linked via intermolecular N—H⋯O hydrogen bonds into chains running parallel to the c axis.

Related literature

For the synthesis, see: Houlihan et al. (1981 ). For standard bond lengths, see: Allen et al. (1987 ). For related structures, see: Cockroft et al. (2007 ).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.11
Monoclinic, P 2₁ /c
a = 12.378 (3) Å
b = 11.657 (2) Å
c = 17.525 (4) Å
β = 91.43 (3)°
V = 2527.9 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.866, T_max = 0.952
4807 measured reflections
4586 independent reflections
2154 reflections with I > 2σ(I)
R_int = 0.029
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.168
S = 1.00
4586 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.09	2.927 (5)	163
N2—H2B⋯O1ⁱⁱ	0.86	1.99	2.830 (5)	165
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019222/pv2414sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019222/pv2414Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019222/pv2414Isup3.cml

checkCIF report

Comment top

In the title compound (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). There are two independent molecules in an asymmetric unit. The dihedral angle between phenyl (C1–C6) and dichlorophenyl (C8–C13) rings in one molecule is 48.5 (3)° compared to 65.1 (3)° in the other molecule. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains running parallel to the c-axis (Fig. 2). The structure is further stabilized by intramolecular interactions of the type C—H···O (Table 1).

Related literature top

For the synthesis, see: Houlihan et al. (1981). For standard bond lengths, see: Allen et al. (1987). For related structures, see: Cockroft et al. (2007).

Experimental top

The title compound was prepared by following a reported procedure (Houlihan et al., 1981). A mixture of aniline (2.8 g, 0.03 mol), 2,6-dichlorobenzoyl chloride (6.3 g, 0.03 mol), and 6 ml triethylamine in 50 ml anhydrous tetrahydrofuran was stirred and refluxed for 8 h and then allowed to stand at room temperature. The resulting solid was filtered off and washed with water (2× 30 ml), dried over sodium sulfate (yield: 7.2 g, 90%). The title compound was purified by crystallizing from ethanol yielding crystals suitable for X-ray diffraction analysis.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. The intermolecular hydrogen bonds are shown as dashed lines; H-atoms not involved in H-bonding have been excluded for clarity.

2,6-Dichloro-N-phenylbenzamide top

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 1088
M_r = 266.11	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.378 (3) Å	θ = 9–13°
b = 11.657 (2) Å	µ = 0.50 mm⁻¹
c = 17.525 (4) Å	T = 293 K
β = 91.43 (3)°	Block, colourless
V = 2527.9 (9) Å³	0.30 × 0.10 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	2154 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.3°, θ_min = 1.7°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
T_min = 0.866, T_max = 0.952	l = −21→21
4807 measured reflections	3 standard reflections every 200 reflections
4586 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
4586 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₃H₉Cl₂NO	V = 2527.9 (9) Å³
M_r = 266.11	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.378 (3) Å	µ = 0.50 mm⁻¹
b = 11.657 (2) Å	T = 293 K
c = 17.525 (4) Å	0.30 × 0.10 × 0.10 mm
β = 91.43 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2154 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.029
T_min = 0.866, T_max = 0.952	3 standard reflections every 200 reflections
4807 measured reflections	intensity decay: 1%
4586 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.00	Δρ_max = 0.24 e Å⁻³
4586 reflections	Δρ_min = −0.36 e Å⁻³
307 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.97924 (12)	0.86429 (16)	−0.00070 (10)	0.1283 (6)
N1	1.2544 (2)	0.8856 (3)	0.00933 (17)	0.0602 (9)
H1A	1.2464	0.8846	0.0579	0.072*
O1	1.2151 (2)	0.7888 (3)	−0.10032 (14)	0.0815 (9)
C1	1.3839 (4)	0.9621 (4)	−0.0806 (3)	0.0815 (13)
H1B	1.3899	0.8905	−0.1035	0.098*
Cl2	1.31603 (18)	0.57910 (17)	0.01462 (10)	0.1680 (9)
C2	1.4429 (4)	1.0533 (5)	−0.1066 (3)	0.0895 (15)
H2A	1.4888	1.0421	−0.1471	0.107*
C3	1.4363 (4)	1.1573 (5)	−0.0756 (3)	0.0950 (16)
H3A	1.4769	1.2179	−0.0942	0.114*
C4	1.3676 (5)	1.1736 (4)	−0.0149 (3)	0.1019 (17)
H4A	1.3620	1.2457	0.0075	0.122*
C5	1.3076 (4)	1.0833 (4)	0.0123 (3)	0.0827 (13)
H5A	1.2615	1.0945	0.0528	0.099*
C6	1.3161 (3)	0.9770 (4)	−0.0205 (2)	0.0566 (10)
C7	1.2075 (3)	0.8004 (3)	−0.0308 (2)	0.0564 (10)
C8	1.1439 (4)	0.7168 (4)	0.0145 (2)	0.0638 (11)
C9	1.1858 (5)	0.6147 (5)	0.0379 (3)	0.1027 (19)
C10	1.1226 (9)	0.5356 (7)	0.0811 (4)	0.147 (3)
H10A	1.1506	0.4658	0.0981	0.177*
C11	1.0196 (9)	0.5681 (8)	0.0959 (5)	0.164 (5)
H11A	0.9770	0.5185	0.1238	0.197*
C12	0.9770 (6)	0.6660 (7)	0.0728 (3)	0.129 (2)
H12A	0.9061	0.6841	0.0843	0.155*
C13	1.0376 (5)	0.7408 (4)	0.0320 (2)	0.0881 (15)
Cl3	0.66623 (13)	0.16121 (13)	0.29111 (9)	0.1217 (6)
Cl4	0.69136 (12)	0.58215 (11)	0.17119 (8)	0.1060 (5)
O2	0.7863 (2)	0.4326 (3)	0.32969 (15)	0.0806 (9)
N2	0.8572 (2)	0.3470 (3)	0.22519 (16)	0.0549 (8)
H2B	0.8389	0.3164	0.1821	0.066*
C14	1.0337 (3)	0.2715 (4)	0.2072 (2)	0.0687 (11)
H14A	1.0021	0.2178	0.1743	0.082*
C15	1.1440 (4)	0.2708 (4)	0.2186 (3)	0.0863 (14)
H15A	1.1866	0.2176	0.1935	0.104*
C16	1.1907 (4)	0.3504 (5)	0.2678 (3)	0.0919 (15)
H16A	1.2651	0.3510	0.2762	0.110*
C17	1.1277 (4)	0.4273 (5)	0.3037 (3)	0.0875 (15)
H17A	1.1596	0.4807	0.3366	0.105*
C18	1.0159 (4)	0.4280 (4)	0.2922 (2)	0.0740 (12)
H18A	0.9735	0.4811	0.3174	0.089*
C19	0.9687 (3)	0.3490 (3)	0.2431 (2)	0.0562 (10)
C20	0.7758 (3)	0.3869 (3)	0.2669 (2)	0.0579 (10)
C21	0.6667 (3)	0.3711 (4)	0.2297 (2)	0.0549 (10)
C22	0.6084 (4)	0.2723 (4)	0.2402 (2)	0.0726 (12)
C23	0.5063 (5)	0.2590 (5)	0.2082 (3)	0.0966 (17)
H23A	0.4684	0.1911	0.2154	0.116*
C24	0.4610 (4)	0.3457 (7)	0.1659 (3)	0.109 (2)
H24A	0.3915	0.3377	0.1452	0.131*
C25	0.5177 (4)	0.4442 (6)	0.1540 (3)	0.0988 (18)
H25A	0.4874	0.5027	0.1244	0.119*
C26	0.6198 (4)	0.4571 (4)	0.1857 (2)	0.0722 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1012 (11)	0.1715 (16)	0.1128 (12)	0.0422 (11)	0.0185 (9)	0.0025 (11)
N1	0.071 (2)	0.075 (2)	0.0347 (16)	−0.0089 (19)	0.0004 (15)	−0.0037 (16)
O1	0.096 (2)	0.110 (2)	0.0395 (16)	−0.0249 (19)	0.0091 (14)	−0.0131 (16)
C1	0.086 (3)	0.092 (4)	0.067 (3)	−0.003 (3)	0.011 (3)	−0.003 (3)
Cl2	0.227 (2)	0.1771 (17)	0.0973 (12)	0.1220 (17)	−0.0434 (12)	−0.0265 (11)
C2	0.082 (3)	0.112 (4)	0.076 (3)	−0.012 (3)	0.016 (3)	0.022 (3)
C3	0.103 (4)	0.099 (4)	0.082 (4)	−0.024 (4)	−0.009 (3)	0.028 (3)
C4	0.134 (5)	0.073 (4)	0.098 (4)	−0.017 (4)	−0.005 (4)	−0.008 (3)
C5	0.100 (4)	0.079 (3)	0.069 (3)	−0.011 (3)	0.005 (3)	−0.005 (3)
C6	0.058 (2)	0.069 (3)	0.043 (2)	−0.006 (2)	−0.0025 (19)	0.006 (2)
C7	0.065 (3)	0.064 (3)	0.041 (2)	0.000 (2)	−0.0014 (19)	−0.004 (2)
C8	0.094 (3)	0.058 (3)	0.039 (2)	−0.012 (3)	−0.001 (2)	0.000 (2)
C9	0.177 (6)	0.077 (4)	0.053 (3)	0.011 (4)	−0.020 (3)	0.000 (3)
C10	0.277 (11)	0.083 (5)	0.080 (5)	−0.002 (7)	−0.042 (6)	0.012 (4)
C11	0.269 (13)	0.133 (8)	0.091 (5)	−0.096 (9)	−0.009 (7)	0.028 (5)
C12	0.142 (6)	0.162 (7)	0.084 (4)	−0.058 (6)	0.031 (4)	−0.007 (4)
C13	0.108 (4)	0.109 (4)	0.048 (3)	−0.043 (3)	0.014 (3)	−0.002 (3)
Cl3	0.1448 (13)	0.1094 (11)	0.1111 (11)	−0.0318 (10)	0.0069 (9)	0.0454 (9)
Cl4	0.1334 (12)	0.0765 (9)	0.1080 (10)	0.0172 (8)	−0.0024 (9)	0.0099 (8)
O2	0.092 (2)	0.109 (2)	0.0412 (15)	−0.0032 (19)	0.0053 (14)	−0.0202 (16)
N2	0.056 (2)	0.067 (2)	0.0414 (17)	0.0034 (17)	−0.0032 (15)	−0.0082 (15)
C14	0.067 (3)	0.063 (3)	0.076 (3)	0.003 (2)	−0.005 (2)	−0.009 (2)
C15	0.061 (3)	0.103 (4)	0.095 (4)	0.014 (3)	0.000 (3)	−0.006 (3)
C16	0.067 (3)	0.113 (4)	0.095 (4)	0.000 (3)	−0.010 (3)	0.005 (3)
C17	0.079 (4)	0.103 (4)	0.080 (3)	−0.016 (3)	−0.023 (3)	−0.007 (3)
C18	0.072 (3)	0.081 (3)	0.069 (3)	−0.002 (3)	−0.010 (2)	−0.011 (2)
C19	0.063 (3)	0.060 (3)	0.045 (2)	−0.003 (2)	−0.0066 (19)	0.0000 (19)
C20	0.068 (3)	0.066 (3)	0.039 (2)	0.001 (2)	0.008 (2)	0.000 (2)
C21	0.055 (2)	0.068 (3)	0.042 (2)	0.007 (2)	0.0118 (18)	−0.006 (2)
C22	0.068 (3)	0.091 (4)	0.059 (3)	−0.005 (3)	0.015 (2)	−0.006 (3)
C23	0.074 (4)	0.130 (5)	0.088 (4)	−0.020 (4)	0.032 (3)	−0.027 (4)
C24	0.049 (3)	0.182 (7)	0.097 (4)	0.011 (4)	0.000 (3)	−0.047 (5)
C25	0.069 (4)	0.143 (6)	0.083 (4)	0.039 (4)	−0.008 (3)	−0.021 (4)
C26	0.066 (3)	0.088 (3)	0.062 (3)	0.021 (3)	0.006 (2)	−0.011 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.704 (6)	Cl3—C22	1.719 (5)
N1—C7	1.341 (4)	Cl4—C26	1.728 (5)
N1—C6	1.418 (5)	O2—C20	1.226 (4)
N1—H1A	0.8600	N2—C20	1.343 (4)
O1—C7	1.232 (4)	N2—C19	1.409 (4)
C1—C2	1.374 (6)	N2—H2B	0.8600
C1—C6	1.374 (5)	C14—C19	1.373 (5)
C1—H1B	0.9300	C14—C15	1.375 (5)
Cl2—C9	1.723 (7)	C14—H14A	0.9300
C2—C3	1.331 (7)	C15—C16	1.384 (6)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.393 (7)	C16—C17	1.354 (6)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.380 (6)	C17—C18	1.393 (6)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.371 (6)	C18—C19	1.380 (5)
C5—H5A	0.9300	C18—H18A	0.9300
C7—C8	1.494 (5)	C20—C21	1.496 (5)
C8—C9	1.358 (6)	C21—C22	1.374 (5)
C8—C13	1.387 (6)	C21—C26	1.383 (5)
C9—C10	1.437 (10)	C22—C23	1.378 (6)
C10—C11	1.361 (11)	C23—C24	1.367 (7)
C10—H10A	0.9300	C23—H23A	0.9300
C11—C12	1.317 (10)	C24—C25	1.365 (8)
C11—H11A	0.9300	C24—H24A	0.9300
C12—C13	1.365 (7)	C25—C26	1.375 (6)
C12—H12A	0.9300	C25—H25A	0.9300

C7—N1—C6	126.4 (3)	C20—N2—C19	128.2 (3)
C7—N1—H1A	116.8	C20—N2—H2B	115.9
C6—N1—H1A	116.8	C19—N2—H2B	115.9
C2—C1—C6	119.8 (5)	C19—C14—C15	121.9 (4)
C2—C1—H1B	120.1	C19—C14—H14A	119.0
C6—C1—H1B	120.1	C15—C14—H14A	119.0
C3—C2—C1	122.1 (5)	C14—C15—C16	118.9 (5)
C3—C2—H2A	119.0	C14—C15—H15A	120.5
C1—C2—H2A	119.0	C16—C15—H15A	120.5
C2—C3—C4	118.7 (5)	C17—C16—C15	119.9 (5)
C2—C3—H3A	120.6	C17—C16—H16A	120.1
C4—C3—H3A	120.6	C15—C16—H16A	120.1
C5—C4—C3	120.3 (5)	C16—C17—C18	121.2 (5)
C5—C4—H4A	119.9	C16—C17—H17A	119.4
C3—C4—H4A	119.9	C18—C17—H17A	119.4
C6—C5—C4	119.8 (5)	C19—C18—C17	119.3 (4)
C6—C5—H5A	120.1	C19—C18—H18A	120.4
C4—C5—H5A	120.1	C17—C18—H18A	120.4
C5—C6—C1	119.4 (4)	C14—C19—C18	118.8 (4)
C5—C6—N1	118.5 (4)	C14—C19—N2	118.0 (3)
C1—C6—N1	122.1 (4)	C18—C19—N2	123.2 (4)
O1—C7—N1	123.9 (4)	O2—C20—N2	125.1 (4)
O1—C7—C8	120.6 (4)	O2—C20—C21	121.3 (4)
N1—C7—C8	115.6 (3)	N2—C20—C21	113.7 (3)
C9—C8—C13	117.9 (5)	C22—C21—C26	117.9 (4)
C9—C8—C7	122.0 (5)	C22—C21—C20	121.1 (4)
C13—C8—C7	120.1 (4)	C26—C21—C20	121.0 (4)
C8—C9—C10	120.8 (7)	C21—C22—C23	121.3 (5)
C8—C9—Cl2	119.5 (5)	C21—C22—Cl3	119.2 (4)
C10—C9—Cl2	119.7 (6)	C23—C22—Cl3	119.4 (5)
C11—C10—C9	116.5 (8)	C24—C23—C22	119.8 (5)
C11—C10—H10A	121.7	C24—C23—H23A	120.1
C9—C10—H10A	121.7	C22—C23—H23A	120.1
C12—C11—C10	123.6 (10)	C25—C24—C23	119.9 (5)
C12—C11—H11A	118.2	C25—C24—H24A	120.0
C10—C11—H11A	118.2	C23—C24—H24A	120.0
C11—C12—C13	119.6 (8)	C24—C25—C26	120.1 (6)
C11—C12—H12A	120.2	C24—C25—H25A	119.9
C13—C12—H12A	120.2	C26—C25—H25A	119.9
C12—C13—C8	121.6 (6)	C25—C26—C21	121.0 (5)
C12—C13—Cl1	118.8 (5)	C25—C26—Cl4	120.1 (4)
C8—C13—Cl1	119.5 (4)	C21—C26—Cl4	118.9 (4)

C6—C1—C2—C3	−0.3 (8)	C19—C14—C15—C16	0.2 (7)
C1—C2—C3—C4	0.1 (8)	C14—C15—C16—C17	−0.1 (8)
C2—C3—C4—C5	0.0 (8)	C15—C16—C17—C18	0.2 (8)
C3—C4—C5—C6	0.2 (8)	C16—C17—C18—C19	−0.3 (7)
C4—C5—C6—C1	−0.5 (7)	C15—C14—C19—C18	−0.4 (6)
C4—C5—C6—N1	179.2 (4)	C15—C14—C19—N2	176.9 (4)
C2—C1—C6—C5	0.5 (7)	C17—C18—C19—C14	0.4 (6)
C2—C1—C6—N1	−179.2 (4)	C17—C18—C19—N2	−176.8 (4)
C7—N1—C6—C5	143.6 (4)	C20—N2—C19—C14	158.0 (4)
C7—N1—C6—C1	−36.8 (6)	C20—N2—C19—C18	−24.8 (6)
C6—N1—C7—O1	2.4 (6)	C19—N2—C20—O2	−0.4 (6)
C6—N1—C7—C8	−178.1 (4)	C19—N2—C20—C21	179.5 (4)
O1—C7—C8—C9	81.7 (5)	O2—C20—C21—C22	−91.6 (5)
N1—C7—C8—C9	−97.9 (5)	N2—C20—C21—C22	88.5 (4)
O1—C7—C8—C13	−96.4 (5)	O2—C20—C21—C26	86.2 (5)
N1—C7—C8—C13	84.1 (5)	N2—C20—C21—C26	−93.7 (4)
C13—C8—C9—C10	−1.6 (7)	C26—C21—C22—C23	−0.2 (6)
C7—C8—C9—C10	−179.7 (5)	C20—C21—C22—C23	177.7 (4)
C13—C8—C9—Cl2	177.8 (3)	C26—C21—C22—Cl3	177.3 (3)
C7—C8—C9—Cl2	−0.3 (6)	C20—C21—C22—Cl3	−4.9 (5)
C8—C9—C10—C11	0.9 (10)	C21—C22—C23—C24	−0.8 (7)
Cl2—C9—C10—C11	−178.5 (6)	Cl3—C22—C23—C24	−178.2 (4)
C9—C10—C11—C12	0.0 (13)	C22—C23—C24—C25	1.4 (8)
C10—C11—C12—C13	−0.2 (13)	C23—C24—C25—C26	−1.2 (8)
C11—C12—C13—C8	−0.6 (9)	C24—C25—C26—C21	0.2 (7)
C11—C12—C13—Cl1	177.3 (6)	C24—C25—C26—Cl4	−179.6 (4)
C9—C8—C13—C12	1.5 (7)	C22—C21—C26—C25	0.5 (6)
C7—C8—C13—C12	179.6 (4)	C20—C21—C26—C25	−177.4 (4)
C9—C8—C13—Cl1	−176.4 (3)	C22—C21—C26—Cl4	−179.8 (3)
C7—C8—C13—Cl1	1.7 (5)	C20—C21—C26—Cl4	2.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.09	2.927 (5)	163
N2—H2B···O1ⁱⁱ	0.86	1.99	2.830 (5)	165
C1—H1B···O1	0.93	2.46	2.920 (7)	110
C18—H18A···O2	0.93	2.41	2.937 (6)	116

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.378 (3), 11.657 (2), 17.525 (4)
β (°)	91.43 (3)
V (Å³)	2527.9 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.866, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	4807, 4586, 2154
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.168, 1.00
No. of reflections	4586
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.36

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.09	2.927 (5)	163
N2—H2B···O1ⁱⁱ	0.86	1.99	2.830 (5)	165
C1—H1B···O1	0.93	2.46	2.920 (7)	110
C18—H18A···O2	0.93	2.41	2.937 (6)	116

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z.

Acknowledgements

The authors thank Bonian Liu from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

References

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