3-Chloro-N-(3-chloro­phen­yl)benzamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808012099

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o949

doi:10.1107/S1600536808012099

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3-Chloro-N-(3-chlorophenyl)benzamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 22 April 2008; accepted 25 April 2008; online 30 April 2008)

In the crystal structure of the title compound, C₁₃H₉Cl₂NO, the N—H and C=O bonds are anti to each other in the two independent molecules. In one molecule, the N—H bond is syn to the meta-chloro group of the attached ring; it is anti in the other molecule. This relationship is also observed between the C=O bond and the meta-chloro substituent of its attached ring. The amide –NHCO– group makes dihedral angles of 31.5 (4) and 34.7 (3)° with the aniline rings; it makes dihedral angles of 37.4 (3) and 37.2 (3)° with the benzoyl rings. The two rings are nearly coplanar, with dihedral angles of 9.1 (2) and 7.3 (3)° in the two independent molecules. Adjacent molecules are linked into infinite chains through N—H⋯O hydrogen bonds.

Related literature

For background literature, see: Gowda et al. (2003 , 2007 , 2008 ).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.11
Monoclinic, P 2₁
a = 8.577 (1) Å
b = 13.551 (1) Å
c = 10.357 (1) Å
β = 93.04 (1)°
V = 1202.1 (2) Å³
Z = 4
Cu Kα radiation
μ = 4.70 mm⁻¹
T = 296 (2) K
0.60 × 0.28 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.265, T_max = 0.341
3088 measured reflections
2249 independent reflections
2165 reflections with I > 2˘I)
R_int = 0.022
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.131
S = 1.10
2249 reflections
308 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ), no Friedel pairs
Flack parameter: 0.07 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2ⁱ	0.86	2.05	2.877 (4)	162
N2—H2n⋯O1	0.86	2.06	2.884 (5)	161
Symmetry code: (i) x+1, y, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012099/ng2449sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012099/ng2449Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the structures of N-aromatic amides,in the present work, the structure of 3-Chloro-N-(3-chlorophenyl)- benzamide(N3CP3CBA) has been determined(Gowda et al., 2003; 2007, 2008). In the structure of N3CP3CBA (Fig. 1),the conformations of the N—H and C=O bonds are anti to each other. The asymmetric unit of the structure contains two molecules. In one of the molecules, the conformation of the N—H bond is syn to the meta-chloro group in the aniline ring and anti to each other in the other molecule. Similar conformations were observed between the C=O bond and meta-chloro substituent in the benzoyl ring. This is in contrast to the single molecule observed in the asymmetric unit of 2-chloro-N-(2-Chlorophenyl)-benzamide (N2CP2CBA) and syn conformation of the N—H bond to the ortho-chloro substituent in the aniline ring and the C=O bond to the ortho-chloro substituent in the benzoyl ring (Gowda et al., 2007). The bond parameters in N3CP3CBA are similar to those in N-(3-chlorophenyl)-benzamide, N2CP2CBA and other benzanilides (Gowda et al., 2003; 2008). The amide group,-NHCO– makes the dihedral angles of 31.5 (4), 37.4 (3)° (molecule 1) and 34.7 (3), 37.2 (3)° (molecule 2) with the aniline and benzoyl rings, respectively, while those between the benzoyl and aniline rings are 9.1 (2)° and 7.3 (3)° in the molecules 1 and 2, respectively. The packing diagram of N3CP3CBA molecules showing the hydrogen bonds N1—H1N···O2 and N2—H2N···O1 (Table 1) involved in the formation of molecular chains is given in Fig. 2.

Related literature top

For background literature, see: Gowda et al. (2003, 2007, 2008).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines..

3-Chloro-N-(3-chlorophenyl)benzamide top

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 544
M_r = 266.11	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 8.577 (1) Å	θ = 6.5–27.0°
b = 13.551 (1) Å	µ = 4.70 mm⁻¹
c = 10.357 (1) Å	T = 296 K
β = 93.04 (1)°	Thick needle, colourless
V = 1202.1 (2) Å³	0.60 × 0.28 × 0.23 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2165 reflections with I > 2˘I)
Radiation source: medium-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 67.0°, θ_min = 4.3°
ω–2θ scans	h = −10→3
Absorption correction: ψ scan (North et al., 1968)	k = −16→0
T_min = 0.265, T_max = 0.341	l = −12→12
3088 measured reflections	3 standard reflections every 120 min
2249 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0835P)² + 0.4755P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.131	(Δ/σ)_max = 0.010
S = 1.10	Δρ_max = 0.37 e Å⁻³
2249 reflections	Δρ_min = −0.50 e Å⁻³
308 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0062 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: No Flack (1983), no Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.07 (2)

Crystal data top

C₁₃H₉Cl₂NO	V = 1202.1 (2) Å³
M_r = 266.11	Z = 4
Monoclinic, P2₁	Cu Kα radiation
a = 8.577 (1) Å	µ = 4.70 mm⁻¹
b = 13.551 (1) Å	T = 296 K
c = 10.357 (1) Å	0.60 × 0.28 × 0.23 mm
β = 93.04 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2165 reflections with I > 2˘I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.022
T_min = 0.265, T_max = 0.341	3 standard reflections every 120 min
3088 measured reflections	intensity decay: none
2249 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.131	Δρ_max = 0.37 e Å⁻³
S = 1.10	Δρ_min = −0.50 e Å⁻³
2249 reflections	Absolute structure: No Flack (1983), no Friedel pairs
308 parameters	Absolute structure parameter: 0.07 (2)
1 restraint

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	0.32030 (17)	−0.00289 (12)	−0.13075 (14)	0.0740 (5)
Cl2	1.14912 (18)	0.14458 (13)	0.63527 (15)	0.0799 (5)
O1	0.5608 (3)	0.1667 (2)	0.2587 (3)	0.0503 (8)
N1	0.7425 (4)	0.0481 (3)	0.2308 (4)	0.0460 (8)
H1N	0.8369	0.0308	0.2520	0.055*
C1	0.6552 (5)	−0.0173 (3)	0.1482 (4)	0.0431 (10)
C2	0.5418 (5)	0.0182 (4)	0.0581 (4)	0.0456 (10)
H2	0.5206	0.0853	0.0511	0.055*
C3	0.4622 (5)	−0.0494 (4)	−0.0200 (4)	0.0445 (10)
C4	0.4926 (6)	−0.1489 (4)	−0.0152 (5)	0.0515 (11)
H4	0.4385	−0.1926	−0.0703	0.062*
C5	0.6063 (6)	−0.1817 (4)	0.0742 (4)	0.0535 (11)
H5	0.6279	−0.2489	0.0807	0.064*
C6	0.6879 (5)	−0.1163 (4)	0.1537 (4)	0.0488 (10)
H6	0.7660	−0.1394	0.2117	0.059*
C7	0.6948 (4)	0.1331 (3)	0.2792 (4)	0.0422 (9)
C8	0.8119 (4)	0.1892 (4)	0.3622 (4)	0.0393 (9)
C9	0.9189 (5)	0.1425 (4)	0.4483 (4)	0.0441 (9)
H9	0.9228	0.0741	0.4541	0.053*
C10	1.0191 (5)	0.2006 (4)	0.5251 (4)	0.0459 (10)
C11	1.0193 (6)	0.3013 (4)	0.5145 (5)	0.0485 (10)
H11	1.0898	0.3389	0.5649	0.058*
C12	0.9142 (5)	0.3464 (4)	0.4286 (5)	0.0496 (11)
H12	0.9139	0.4148	0.4208	0.060*
C13	0.8099 (5)	0.2910 (4)	0.3546 (4)	0.0456 (10)
H13	0.7371	0.3222	0.2987	0.055*
Cl3	0.1457 (2)	0.46405 (11)	0.18206 (16)	0.0753 (4)
Cl4	0.39972 (18)	−0.34554 (10)	0.31885 (16)	0.0731 (4)
O2	0.0590 (3)	−0.0229 (2)	0.2416 (3)	0.0517 (8)
N2	0.2432 (4)	0.0962 (3)	0.2377 (4)	0.0485 (9)
H2N	0.3378	0.1108	0.2621	0.058*
C14	0.1548 (5)	0.1709 (3)	0.1702 (4)	0.0428 (10)
C15	0.1861 (5)	0.2671 (4)	0.2042 (4)	0.0465 (10)
H15	0.2607	0.2819	0.2697	0.056*
C16	0.1049 (6)	0.3412 (4)	0.1395 (5)	0.0502 (11)
C17	−0.0064 (6)	0.3217 (4)	0.0413 (5)	0.0576 (12)
H17	−0.0604	0.3727	−0.0011	0.069*
C18	−0.0353 (6)	0.2251 (4)	0.0079 (5)	0.0604 (13)
H18	−0.1089	0.2106	−0.0585	0.072*
C19	0.0435 (6)	0.1493 (4)	0.0719 (4)	0.0532 (10)
H19	0.0222	0.0841	0.0493	0.064*
C20	0.1947 (5)	0.0069 (3)	0.2667 (4)	0.0433 (9)
C21	0.3143 (5)	−0.0594 (3)	0.3333 (4)	0.0425 (9)
C22	0.3057 (5)	−0.1578 (4)	0.3017 (4)	0.0425 (10)
H22	0.2313	−0.1802	0.2400	0.051*
C23	0.4090 (5)	−0.2227 (3)	0.3627 (4)	0.0464 (10)
C24	0.5166 (5)	−0.1926 (4)	0.4561 (5)	0.0518 (11)
H24	0.5846	−0.2378	0.4966	0.062*
C25	0.5229 (6)	−0.0953 (4)	0.4891 (5)	0.0560 (12)
H25	0.5951	−0.0742	0.5535	0.067*
C26	0.4227 (5)	−0.0268 (4)	0.4277 (4)	0.0477 (10)
H26	0.4286	0.0397	0.4498	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0702 (8)	0.0747 (9)	0.0728 (8)	−0.0055 (7)	−0.0370 (6)	0.0012 (7)
Cl2	0.0704 (8)	0.0792 (10)	0.0852 (10)	−0.0037 (8)	−0.0431 (7)	0.0120 (8)
O1	0.0270 (13)	0.052 (2)	0.0705 (19)	0.0027 (12)	−0.0092 (12)	−0.0101 (15)
N1	0.0294 (16)	0.051 (2)	0.056 (2)	0.0007 (15)	−0.0091 (14)	−0.0052 (18)
C1	0.0343 (19)	0.048 (3)	0.046 (2)	−0.0029 (18)	0.0001 (16)	−0.0051 (19)
C2	0.042 (2)	0.045 (2)	0.049 (2)	−0.0022 (18)	−0.0042 (17)	−0.0010 (19)
C3	0.034 (2)	0.056 (3)	0.042 (2)	−0.0049 (19)	−0.0059 (17)	−0.004 (2)
C4	0.047 (2)	0.059 (3)	0.048 (2)	−0.011 (2)	−0.0056 (19)	−0.009 (2)
C5	0.060 (3)	0.046 (3)	0.055 (3)	0.003 (2)	0.003 (2)	−0.006 (2)
C6	0.042 (2)	0.061 (3)	0.042 (2)	0.000 (2)	−0.0042 (17)	−0.001 (2)
C7	0.0293 (18)	0.050 (3)	0.047 (2)	−0.0013 (18)	−0.0030 (15)	0.0009 (19)
C8	0.0307 (18)	0.048 (2)	0.0391 (19)	−0.0065 (17)	−0.0021 (15)	−0.0006 (17)
C9	0.041 (2)	0.042 (2)	0.048 (2)	−0.0057 (19)	−0.0043 (17)	0.0012 (19)
C10	0.037 (2)	0.057 (3)	0.043 (2)	0.0004 (19)	−0.0072 (16)	0.002 (2)
C11	0.047 (2)	0.052 (3)	0.047 (2)	−0.010 (2)	−0.0028 (18)	−0.011 (2)
C12	0.049 (3)	0.041 (2)	0.058 (3)	−0.0035 (19)	0.003 (2)	−0.006 (2)
C13	0.039 (2)	0.049 (3)	0.049 (2)	0.0023 (18)	0.0013 (17)	0.002 (2)
Cl3	0.0863 (10)	0.0465 (7)	0.0935 (10)	0.0010 (7)	0.0074 (8)	0.0058 (7)
Cl4	0.0804 (8)	0.0452 (7)	0.0932 (10)	0.0119 (6)	0.0009 (7)	−0.0068 (7)
O2	0.0252 (13)	0.0485 (18)	0.080 (2)	−0.0024 (13)	−0.0067 (12)	0.0044 (16)
N2	0.0358 (19)	0.047 (2)	0.062 (2)	0.0023 (16)	−0.0041 (16)	0.0028 (19)
C14	0.0340 (19)	0.049 (3)	0.046 (2)	0.0101 (17)	0.0044 (16)	0.0074 (19)
C15	0.040 (2)	0.049 (3)	0.051 (2)	0.0023 (19)	0.0038 (18)	0.0041 (19)
C16	0.049 (2)	0.044 (3)	0.059 (3)	0.0066 (19)	0.009 (2)	0.005 (2)
C17	0.051 (3)	0.062 (3)	0.059 (3)	0.015 (2)	−0.004 (2)	0.015 (2)
C18	0.053 (3)	0.066 (3)	0.060 (3)	0.007 (2)	−0.015 (2)	0.008 (3)
C19	0.060 (3)	0.049 (2)	0.049 (2)	0.004 (2)	−0.0058 (19)	0.002 (2)
C20	0.038 (2)	0.044 (2)	0.048 (2)	0.0064 (18)	−0.0026 (16)	−0.0033 (19)
C21	0.039 (2)	0.045 (2)	0.043 (2)	0.0084 (18)	0.0011 (16)	0.0008 (18)
C22	0.0335 (19)	0.052 (3)	0.041 (2)	0.0070 (18)	−0.0013 (16)	−0.0019 (18)
C23	0.046 (2)	0.042 (2)	0.051 (2)	0.0043 (19)	0.0058 (18)	0.0039 (19)
C24	0.044 (2)	0.051 (3)	0.060 (3)	0.012 (2)	−0.005 (2)	0.012 (2)
C25	0.047 (3)	0.066 (3)	0.054 (2)	−0.004 (2)	−0.013 (2)	0.004 (2)
C26	0.050 (2)	0.040 (2)	0.052 (2)	0.002 (2)	−0.0029 (18)	0.000 (2)

Geometric parameters (Å, º) top

Cl1—C3	1.745 (4)	Cl3—C16	1.753 (5)
Cl2—C10	1.729 (4)	Cl4—C23	1.726 (5)
O1—C7	1.244 (5)	O2—C20	1.246 (5)
N1—C7	1.330 (6)	N2—C20	1.319 (6)
N1—C1	1.418 (5)	N2—C14	1.425 (5)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.370 (7)	C14—C15	1.373 (7)
C1—C2	1.397 (6)	C14—C19	1.390 (6)
C2—C3	1.379 (6)	C15—C16	1.376 (7)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.373 (7)	C16—C17	1.383 (7)
C4—C5	1.383 (7)	C17—C18	1.373 (8)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.376 (7)	C18—C19	1.380 (7)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.493 (6)	C20—C21	1.503 (6)
C8—C13	1.382 (6)	C21—C22	1.374 (6)
C8—C9	1.397 (6)	C21—C26	1.386 (6)
C9—C10	1.385 (6)	C22—C23	1.378 (6)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.369 (7)	C23—C24	1.363 (7)
C11—C12	1.375 (7)	C24—C25	1.364 (8)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.372 (6)	C25—C26	1.395 (7)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300

C7—N1—C1	127.3 (4)	C20—N2—C14	126.6 (4)
C7—N1—H1N	116.3	C20—N2—H2N	116.7
C1—N1—H1N	116.3	C14—N2—H2N	116.7
C6—C1—C2	119.9 (4)	C15—C14—C19	120.3 (4)
C6—C1—N1	119.1 (4)	C15—C14—N2	117.2 (4)
C2—C1—N1	121.0 (4)	C19—C14—N2	122.5 (4)
C3—C2—C1	117.9 (4)	C14—C15—C16	118.8 (4)
C3—C2—H2	121.0	C14—C15—H15	120.6
C1—C2—H2	121.0	C16—C15—H15	120.6
C4—C3—C2	122.9 (5)	C15—C16—C17	122.0 (5)
C4—C3—Cl1	120.2 (4)	C15—C16—Cl3	118.8 (4)
C2—C3—Cl1	116.9 (4)	C17—C16—Cl3	119.2 (4)
C3—C4—C5	117.8 (4)	C18—C17—C16	118.4 (5)
C3—C4—H4	121.1	C18—C17—H17	120.8
C5—C4—H4	121.1	C16—C17—H17	120.8
C6—C5—C4	120.7 (5)	C17—C18—C19	120.8 (5)
C6—C5—H5	119.6	C17—C18—H18	119.6
C4—C5—H5	119.6	C19—C18—H18	119.6
C1—C6—C5	120.6 (4)	C18—C19—C14	119.7 (5)
C1—C6—H6	119.7	C18—C19—H19	120.2
C5—C6—H6	119.7	C14—C19—H19	120.2
O1—C7—N1	123.5 (4)	O2—C20—N2	123.5 (4)
O1—C7—C8	120.0 (4)	O2—C20—C21	120.6 (4)
N1—C7—C8	116.5 (4)	N2—C20—C21	115.9 (4)
C13—C8—C9	119.6 (4)	C22—C21—C26	120.2 (4)
C13—C8—C7	118.0 (4)	C22—C21—C20	116.3 (4)
C9—C8—C7	122.4 (4)	C26—C21—C20	123.3 (4)
C10—C9—C8	118.4 (4)	C21—C22—C23	119.0 (4)
C10—C9—H9	120.8	C21—C22—H22	120.5
C8—C9—H9	120.8	C23—C22—H22	120.5
C11—C10—C9	121.6 (4)	C24—C23—C22	121.9 (5)
C11—C10—Cl2	119.2 (4)	C24—C23—Cl4	119.7 (4)
C9—C10—Cl2	119.2 (4)	C22—C23—Cl4	118.4 (4)
C10—C11—C12	119.4 (5)	C25—C24—C23	118.9 (4)
C10—C11—H11	120.3	C25—C24—H24	120.5
C12—C11—H11	120.3	C23—C24—H24	120.5
C13—C12—C11	120.3 (5)	C24—C25—C26	120.9 (5)
C13—C12—H12	119.9	C24—C25—H25	119.5
C11—C12—H12	119.9	C26—C25—H25	119.5
C12—C13—C8	120.6 (4)	C21—C26—C25	118.9 (5)
C12—C13—H13	119.7	C21—C26—H26	120.5
C8—C13—H13	119.7	C25—C26—H26	120.5

C7—N1—C1—C6	−150.4 (5)	C20—N2—C14—C15	147.2 (5)
C7—N1—C1—C2	32.5 (7)	C20—N2—C14—C19	−34.2 (7)
C6—C1—C2—C3	2.2 (6)	C19—C14—C15—C16	0.3 (6)
N1—C1—C2—C3	179.4 (4)	N2—C14—C15—C16	178.9 (4)
C1—C2—C3—C4	−1.8 (7)	C14—C15—C16—C17	−0.3 (7)
C1—C2—C3—Cl1	179.6 (3)	C14—C15—C16—Cl3	−179.6 (3)
C2—C3—C4—C5	1.3 (7)	C15—C16—C17—C18	−0.3 (8)
Cl1—C3—C4—C5	179.9 (4)	Cl3—C16—C17—C18	179.1 (4)
C3—C4—C5—C6	−1.2 (7)	C16—C17—C18—C19	0.8 (8)
C2—C1—C6—C5	−2.3 (7)	C17—C18—C19—C14	−0.8 (8)
N1—C1—C6—C5	−179.5 (4)	C15—C14—C19—C18	0.2 (7)
C4—C5—C6—C1	1.7 (7)	N2—C14—C19—C18	−178.3 (4)
C1—N1—C7—O1	1.2 (7)	C14—N2—C20—O2	−2.7 (7)
C1—N1—C7—C8	−178.8 (4)	C14—N2—C20—C21	177.2 (4)
O1—C7—C8—C13	−36.2 (6)	O2—C20—C21—C22	35.5 (6)
N1—C7—C8—C13	143.8 (4)	N2—C20—C21—C22	−144.4 (4)
O1—C7—C8—C9	142.1 (4)	O2—C20—C21—C26	−140.5 (4)
N1—C7—C8—C9	−37.9 (6)	N2—C20—C21—C26	39.5 (6)
C13—C8—C9—C10	0.8 (6)	C26—C21—C22—C23	−1.7 (6)
C7—C8—C9—C10	−177.5 (4)	C20—C21—C22—C23	−177.9 (4)
C8—C9—C10—C11	−2.6 (7)	C21—C22—C23—C24	1.9 (7)
C8—C9—C10—Cl2	178.4 (3)	C21—C22—C23—Cl4	−178.4 (3)
C9—C10—C11—C12	2.1 (8)	C22—C23—C24—C25	−0.6 (7)
Cl2—C10—C11—C12	−178.8 (4)	Cl4—C23—C24—C25	179.7 (4)
C10—C11—C12—C13	0.2 (7)	C23—C24—C25—C26	−0.8 (8)
C11—C12—C13—C8	−2.0 (7)	C22—C21—C26—C25	0.3 (6)
C9—C8—C13—C12	1.5 (7)	C20—C21—C26—C25	176.3 (4)
C7—C8—C13—C12	179.8 (4)	C24—C25—C26—C21	0.9 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2ⁱ	0.86	2.05	2.877 (4)	162
N2—H2n···O1	0.86	2.06	2.884 (5)	161

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.577 (1), 13.551 (1), 10.357 (1)
β (°)	93.04 (1)
V (Å³)	1202.1 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.70
Crystal size (mm)	0.60 × 0.28 × 0.23

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.265, 0.341
No. of measured, independent and observed [I > 2˘I)] reflections	3088, 2249, 2165
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.131, 1.10
No. of reflections	2249
No. of parameters	308
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.50
Absolute structure	No Flack (1983), no Friedel pairs
Absolute structure parameter	0.07 (2)

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2ⁱ	0.86	2.05	2.877 (4)	161.7
N2—H2n···O1	0.86	2.06	2.884 (5)	160.5

Symmetry code: (i) x+1, y, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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