2-Chloro-N-(2,3-dichloro­phen­yl)benzamide

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

doi:10.1107/S1600536808018679

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1342

doi:10.1107/S1600536808018679

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2-Chloro-N-(2,3-dichlorophenyl)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 16 June 2008; accepted 20 June 2008; online 25 June 2008)

Two independent molecules comprise the asymmetric unit in the title compound, C₁₃H₈Cl₃NO, each with the amide N—H and C=O bonds trans to each other. The molecules are linked into chains through intermolecular N—H⋯O and N—H⋯Cl hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₃H₈Cl₃NO
M_r = 300.55
Monoclinic, P c
a = 12.310 (1) Å
b = 7.8307 (6) Å
c = 14.407 (2) Å
β = 111.52 (1)°
V = 1292.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 299 (2) K
0.75 × 0.75 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.624, T_max = 0.885
5882 measured reflections
3936 independent reflections
3430 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.104
S = 1.14
3936 reflections
326 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: (Flack, 1983 ), 365 Friedel pairs
Flack parameter: 0.12 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86	2.16	2.850 (3)	137
N1—H1N⋯Cl3	0.86	2.64	3.114 (3)	116
N2—H2N⋯O1ⁱ	0.86	2.05	2.896 (3)	167
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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/S1600536808018679/tk2277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018679/tk2277Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(2,3-dichlorophenyl)- benzamide (I, N23DCP2CBA) has been determined to explore the effect of substituents on the structures of benzanilides (Gowda et al., 2003; 2007; 2008). The amide N—H and C=O bonds in each of the two molecules comprising the crystallographic asymmetric unit are trans to each other (Fig. 1), similar to that observed in 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003), 2-chloro-N-(2-chlorophenyl)-benzamide (N2CP2CBA) (Gowda et al., 2007), and 2-chloro-N-(3-chlorophenyl)-benzamide (N3CP2CBA) (Gowda et al., 2008). In one of the molecules, the conformation of the N—H bond is syn to both the ortho and meta-chloro groups in the aniline ring and of the C=O bond group is also syn to the ortho-chloro group in the benzoyl ring. By contrast, the conformations of these bonds in the second independent molecule are intermediate between syn and anti to the respective groups. The above conformations are in contrast to the syn conformations of both the amide N—H and C=O bonds, with respect to the ortho-chloro groups in the benzoyl and aniline rings, respectively, observed in N2CP2CBA (Gowda et al., 2007). Further, in N3CP2CBA, the conformation of the C=O bond is syn to the ortho-chloro group of the benzoyl ring, while the N—H bond is anti to the meta-chloro group of the aniline ring (Gowda et al., 2008). The –NHCO– group makes the dihedral angles of 42.24 (14)° (molecule 1), 48.89 (12)° (molecule 2), and 35.31 (19)° (molecule 1), 41.88 (13)° (molecule 2) with the benzoyl and aniline rings, respectively. The benzoyl and aniline rings form the dihedral angles of 12.30 (10)° (molecule 1) and 7.25 (9)°) (molecule 2). In the crystal structure of (I), the molecules are linked by intermolecular N—H···O and N—H···Cl hydrogen bonds (Table 1) forming chains running along the a axis, as shown in Fig. 2.

Related literature top

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

Experimental top

Compound (I) was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was confirmed by melting point, and IR and NMR spectra. Single crystals were obtained from an ethanolic solution of (I)

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (I) showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2-Chloro-N-(2,3-dichlorophenyl)benzamide top

Crystal data top

C₁₃H₈Cl₃NO	F(000) = 608
M_r = 300.55	D_x = 1.545 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 3409 reflections
a = 12.310 (1) Å	θ = 2.6–27.5°
b = 7.8307 (6) Å	µ = 0.69 mm⁻¹
c = 14.407 (2) Å	T = 299 K
β = 111.52 (1)°	Thick plate, colourless
V = 1292.0 (2) Å³	0.75 × 0.75 × 0.18 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3936 independent reflections
Radiation source: fine-focus sealed tube	3430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −15→13
T_min = 0.624, T_max = 0.885	k = −9→9
5882 measured reflections	l = −15→18

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0715P)² + 0.0104P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.104	(Δ/σ)_max = 0.003
S = 1.14	Δρ_max = 0.29 e Å⁻³
3936 reflections	Δρ_min = −0.28 e Å⁻³
326 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0118 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: (Flack, 1983), 365 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.12 (5)

Crystal data top

C₁₃H₈Cl₃NO	V = 1292.0 (2) Å³
M_r = 300.55	Z = 4
Monoclinic, Pc	Mo Kα radiation
a = 12.310 (1) Å	µ = 0.69 mm⁻¹
b = 7.8307 (6) Å	T = 299 K
c = 14.407 (2) Å	0.75 × 0.75 × 0.18 mm
β = 111.52 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3936 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3430 reflections with I > 2σ(I)
T_min = 0.624, T_max = 0.885	R_int = 0.014
5882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.104	Δρ_max = 0.29 e Å⁻³
S = 1.14	Δρ_min = −0.28 e Å⁻³
3936 reflections	Absolute structure: (Flack, 1983), 365 Friedel pairs
326 parameters	Absolute structure parameter: 0.12 (5)
2 restraints

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	0.80355 (8)	−0.16289 (10)	0.22458 (7)	0.0542 (2)
Cl2	0.53668 (10)	−0.25096 (14)	0.12596 (9)	0.0739 (3)
Cl3	1.08381 (10)	0.01157 (12)	0.38808 (9)	0.0745 (3)
O1	0.8488 (2)	0.4258 (3)	0.36026 (18)	0.0537 (6)
N1	0.8566 (2)	0.2051 (3)	0.26179 (19)	0.0411 (6)
H1N	0.9028	0.1426	0.2437	0.049*
C1	0.7362 (3)	0.1682 (4)	0.2183 (2)	0.0359 (6)
C2	0.7006 (3)	−0.0018 (4)	0.1965 (2)	0.0420 (7)
C3	0.5819 (3)	−0.0414 (5)	0.1521 (3)	0.0493 (8)
C4	0.4996 (3)	0.0858 (5)	0.1303 (3)	0.0566 (9)
H4	0.4206	0.0589	0.1018	0.068*
C5	0.5342 (4)	0.2543 (5)	0.1510 (3)	0.0597 (10)
H5	0.4783	0.3403	0.1357	0.072*
C6	0.6515 (3)	0.2954 (5)	0.1941 (3)	0.0498 (8)
H6	0.6738	0.4091	0.2071	0.060*
C7	0.9063 (3)	0.3294 (4)	0.3292 (2)	0.0388 (7)
C8	1.0362 (3)	0.3540 (4)	0.3601 (2)	0.0379 (7)
C9	1.1208 (3)	0.2248 (5)	0.3829 (3)	0.0478 (8)
C10	1.2384 (4)	0.2639 (6)	0.4080 (3)	0.0613 (10)
H10	1.2936	0.1769	0.4226	0.074*
C11	1.2727 (3)	0.4310 (6)	0.4112 (3)	0.0629 (10)
H11	1.3513	0.4569	0.4276	0.076*
C12	1.1924 (4)	0.5604 (5)	0.3904 (3)	0.0576 (9)
H12	1.2164	0.6735	0.3931	0.069*
C13	1.0746 (3)	0.5220 (4)	0.3654 (3)	0.0455 (7)
H13	1.0206	0.6104	0.3519	0.055*
Cl4	0.61868 (9)	0.43793 (11)	−0.06792 (10)	0.0700 (3)
Cl5	0.41892 (8)	0.16238 (16)	−0.14120 (9)	0.0747 (3)
Cl6	1.22481 (9)	0.23655 (14)	0.13296 (10)	0.0727 (3)
O2	0.9822 (2)	0.1549 (3)	0.13253 (16)	0.0436 (5)
N2	0.8590 (2)	0.2974 (3)	−0.00345 (19)	0.0400 (6)
H2N	0.8503	0.3882	−0.0390	0.048*
C14	0.7697 (3)	0.1737 (4)	−0.0342 (2)	0.0351 (6)
C15	0.6526 (3)	0.2227 (4)	−0.0670 (2)	0.0412 (7)
C16	0.5648 (3)	0.1028 (4)	−0.0983 (2)	0.0422 (7)
C17	0.5907 (3)	−0.0713 (5)	−0.0947 (3)	0.0485 (8)
H17	0.5314	−0.1525	−0.1133	0.058*
C18	0.7064 (3)	−0.1199 (4)	−0.0630 (3)	0.0471 (8)
H18	0.7250	−0.2351	−0.0618	0.056*
C19	0.7949 (3)	−0.0002 (4)	−0.0329 (2)	0.0413 (7)
H19	0.8723	−0.0359	−0.0115	0.050*
C20	0.9589 (3)	0.2819 (4)	0.0796 (2)	0.0347 (6)
C21	1.0337 (3)	0.4382 (4)	0.1036 (2)	0.0364 (6)
C22	1.1550 (3)	0.4300 (4)	0.1294 (2)	0.0432 (7)
C23	1.2224 (3)	0.5764 (6)	0.1521 (3)	0.0598 (9)
H23	1.3026	0.5697	0.1680	0.072*
C24	1.1699 (4)	0.7327 (5)	0.1510 (3)	0.0635 (11)
H24	1.2149	0.8316	0.1656	0.076*
C25	1.0513 (4)	0.7428 (5)	0.1285 (3)	0.0604 (10)
H25	1.0168	0.8479	0.1297	0.072*
C26	0.9839 (3)	0.5976 (4)	0.1043 (2)	0.0464 (8)
H26	0.9037	0.6060	0.0882	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0515 (5)	0.0378 (4)	0.0674 (5)	0.0092 (4)	0.0148 (4)	−0.0055 (4)
Cl2	0.0619 (7)	0.0521 (5)	0.0969 (8)	−0.0162 (5)	0.0164 (6)	−0.0149 (5)
Cl3	0.0614 (6)	0.0395 (5)	0.1037 (8)	0.0091 (5)	0.0080 (6)	0.0133 (5)
O1	0.0443 (14)	0.0479 (13)	0.0663 (14)	0.0016 (11)	0.0173 (11)	−0.0199 (12)
N1	0.0360 (14)	0.0392 (13)	0.0486 (14)	0.0038 (11)	0.0162 (11)	−0.0078 (11)
C1	0.0353 (15)	0.0343 (15)	0.0375 (15)	0.0061 (12)	0.0127 (12)	−0.0007 (12)
C2	0.0448 (17)	0.0418 (17)	0.0389 (16)	0.0093 (15)	0.0149 (13)	−0.0026 (13)
C3	0.0467 (19)	0.0471 (18)	0.0511 (19)	−0.0055 (16)	0.0147 (15)	−0.0106 (15)
C4	0.0379 (19)	0.060 (2)	0.064 (2)	−0.0022 (17)	0.0095 (15)	−0.0069 (18)
C5	0.043 (2)	0.053 (2)	0.074 (3)	0.0176 (17)	0.0104 (17)	−0.0041 (18)
C6	0.050 (2)	0.0376 (17)	0.055 (2)	0.0071 (15)	0.0115 (15)	−0.0063 (15)
C7	0.0414 (17)	0.0326 (15)	0.0438 (16)	0.0041 (13)	0.0172 (13)	0.0011 (13)
C8	0.0400 (17)	0.0393 (16)	0.0336 (14)	0.0029 (13)	0.0128 (12)	0.0023 (12)
C9	0.0426 (19)	0.0434 (18)	0.0506 (18)	0.0012 (15)	0.0090 (14)	0.0056 (14)
C10	0.044 (2)	0.068 (2)	0.064 (2)	0.0131 (18)	0.0096 (16)	0.0015 (19)
C11	0.042 (2)	0.073 (3)	0.071 (2)	−0.007 (2)	0.0159 (17)	0.003 (2)
C12	0.054 (2)	0.055 (2)	0.065 (2)	−0.0116 (18)	0.0231 (17)	0.0018 (18)
C13	0.0457 (19)	0.0384 (16)	0.0527 (19)	−0.0038 (15)	0.0185 (15)	0.0002 (14)
Cl4	0.0492 (5)	0.0352 (4)	0.1229 (9)	0.0110 (4)	0.0283 (5)	0.0141 (5)
Cl5	0.0330 (4)	0.0743 (7)	0.1059 (8)	0.0019 (5)	0.0126 (4)	0.0079 (6)
Cl6	0.0455 (5)	0.0593 (6)	0.1157 (9)	0.0121 (5)	0.0322 (5)	−0.0116 (6)
O2	0.0459 (13)	0.0357 (11)	0.0453 (11)	0.0033 (10)	0.0119 (9)	0.0058 (9)
N2	0.0359 (14)	0.0321 (12)	0.0449 (14)	0.0007 (11)	0.0065 (11)	0.0086 (10)
C14	0.0328 (15)	0.0351 (15)	0.0367 (14)	−0.0006 (12)	0.0119 (11)	0.0055 (12)
C15	0.0423 (18)	0.0341 (16)	0.0485 (17)	0.0067 (14)	0.0184 (14)	0.0075 (13)
C16	0.0329 (16)	0.0432 (17)	0.0510 (18)	−0.0021 (13)	0.0161 (14)	0.0028 (14)
C17	0.047 (2)	0.0457 (18)	0.0525 (19)	−0.0114 (16)	0.0185 (15)	−0.0047 (15)
C18	0.054 (2)	0.0301 (15)	0.0572 (19)	0.0024 (14)	0.0201 (16)	−0.0038 (14)
C19	0.0352 (16)	0.0394 (16)	0.0454 (17)	0.0053 (14)	0.0101 (13)	0.0010 (13)
C20	0.0359 (16)	0.0339 (14)	0.0383 (15)	0.0072 (13)	0.0184 (12)	0.0006 (12)
C21	0.0363 (16)	0.0335 (15)	0.0374 (15)	0.0019 (13)	0.0111 (12)	−0.0031 (12)
C22	0.0395 (18)	0.0407 (17)	0.0472 (17)	0.0038 (14)	0.0133 (13)	−0.0028 (14)
C23	0.043 (2)	0.067 (2)	0.060 (2)	−0.0104 (19)	0.0078 (16)	−0.0007 (19)
C24	0.077 (3)	0.0399 (19)	0.054 (2)	−0.0137 (19)	−0.0003 (19)	0.0006 (15)
C25	0.074 (3)	0.0357 (17)	0.0509 (19)	0.0061 (18)	−0.0013 (17)	−0.0010 (14)
C26	0.0487 (19)	0.0397 (16)	0.0413 (17)	0.0060 (15)	0.0052 (14)	0.0001 (14)

Geometric parameters (Å, º) top

Cl1—C2	1.728 (3)	Cl4—C15	1.735 (3)
Cl2—C3	1.730 (4)	Cl5—C16	1.735 (3)
Cl3—C9	1.739 (4)	Cl6—C22	1.733 (3)
O1—C7	1.226 (4)	O2—C20	1.222 (4)
N1—C7	1.353 (4)	N2—C20	1.371 (4)
N1—C1	1.411 (4)	N2—C14	1.409 (4)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.391 (5)	C14—C19	1.395 (4)
C1—C2	1.401 (4)	C14—C15	1.396 (4)
C2—C3	1.397 (5)	C15—C16	1.377 (5)
C3—C4	1.373 (5)	C16—C17	1.397 (5)
C4—C5	1.384 (6)	C17—C18	1.380 (5)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.384 (6)	C18—C19	1.381 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.507 (5)	C20—C21	1.493 (4)
C8—C13	1.390 (5)	C21—C26	1.393 (4)
C8—C9	1.402 (5)	C21—C22	1.402 (4)
C9—C10	1.392 (6)	C22—C23	1.382 (5)
C10—C11	1.371 (6)	C23—C24	1.382 (6)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.370 (6)	C24—C25	1.376 (7)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.392 (5)	C25—C26	1.375 (5)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300

C7—N1—C1	126.2 (3)	C20—N2—C14	124.1 (3)
C7—N1—H1N	116.9	C20—N2—H2N	118.0
C1—N1—H1N	116.9	C14—N2—H2N	118.0
C6—C1—C2	118.7 (3)	C19—C14—C15	118.0 (3)
C6—C1—N1	122.2 (3)	C19—C14—N2	121.5 (3)
C2—C1—N1	119.1 (3)	C15—C14—N2	120.5 (3)
C3—C2—C1	120.2 (3)	C16—C15—C14	120.8 (3)
C3—C2—Cl1	119.9 (3)	C16—C15—Cl4	120.1 (3)
C1—C2—Cl1	119.9 (3)	C14—C15—Cl4	119.0 (3)
C4—C3—C2	120.3 (3)	C15—C16—C17	120.8 (3)
C4—C3—Cl2	119.1 (3)	C15—C16—Cl5	121.3 (3)
C2—C3—Cl2	120.6 (3)	C17—C16—Cl5	117.9 (3)
C3—C4—C5	119.9 (3)	C18—C17—C16	118.4 (3)
C3—C4—H4	120.0	C18—C17—H17	120.8
C5—C4—H4	120.0	C16—C17—H17	120.8
C6—C5—C4	120.4 (4)	C17—C18—C19	121.1 (3)
C6—C5—H5	119.8	C17—C18—H18	119.4
C4—C5—H5	119.8	C19—C18—H18	119.4
C5—C6—C1	120.6 (4)	C18—C19—C14	120.8 (3)
C5—C6—H6	119.7	C18—C19—H19	119.6
C1—C6—H6	119.7	C14—C19—H19	119.6
O1—C7—N1	122.3 (3)	O2—C20—N2	123.1 (3)
O1—C7—C8	120.4 (3)	O2—C20—C21	122.6 (3)
N1—C7—C8	117.1 (3)	N2—C20—C21	114.2 (2)
C13—C8—C9	117.5 (3)	C26—C21—C22	117.9 (3)
C13—C8—C7	116.1 (3)	C26—C21—C20	120.0 (3)
C9—C8—C7	126.4 (3)	C22—C21—C20	122.0 (3)
C10—C9—C8	121.0 (3)	C23—C22—C21	120.9 (3)
C10—C9—Cl3	117.6 (3)	C23—C22—Cl6	118.0 (3)
C8—C9—Cl3	121.3 (3)	C21—C22—Cl6	121.1 (3)
C11—C10—C9	119.8 (4)	C22—C23—C24	119.7 (4)
C11—C10—H10	120.1	C22—C23—H23	120.2
C9—C10—H10	120.1	C24—C23—H23	120.2
C12—C11—C10	120.7 (4)	C25—C24—C23	120.3 (4)
C12—C11—H11	119.6	C25—C24—H24	119.9
C10—C11—H11	119.6	C23—C24—H24	119.9
C11—C12—C13	119.7 (4)	C26—C25—C24	120.1 (4)
C11—C12—H12	120.1	C26—C25—H25	119.9
C13—C12—H12	120.1	C24—C25—H25	119.9
C8—C13—C12	121.3 (3)	C25—C26—C21	121.1 (3)
C8—C13—H13	119.4	C25—C26—H26	119.5
C12—C13—H13	119.4	C21—C26—H26	119.5

C7—N1—C1—C6	36.2 (5)	C20—N2—C14—C19	−43.2 (4)
C7—N1—C1—C2	−145.3 (3)	C20—N2—C14—C15	136.7 (3)
C6—C1—C2—C3	−0.5 (5)	C19—C14—C15—C16	−0.8 (4)
N1—C1—C2—C3	−179.1 (3)	N2—C14—C15—C16	179.2 (3)
C6—C1—C2—Cl1	179.5 (3)	C19—C14—C15—Cl4	179.2 (2)
N1—C1—C2—Cl1	0.8 (4)	N2—C14—C15—Cl4	−0.7 (4)
C1—C2—C3—C4	−0.6 (5)	C14—C15—C16—C17	2.3 (5)
Cl1—C2—C3—C4	179.5 (3)	Cl4—C15—C16—C17	−177.8 (3)
C1—C2—C3—Cl2	−179.4 (3)	C14—C15—C16—Cl5	−178.9 (2)
Cl1—C2—C3—Cl2	0.7 (4)	Cl4—C15—C16—Cl5	1.1 (4)
C2—C3—C4—C5	1.0 (6)	C15—C16—C17—C18	−2.6 (5)
Cl2—C3—C4—C5	179.9 (3)	Cl5—C16—C17—C18	178.5 (3)
C3—C4—C5—C6	−0.5 (6)	C16—C17—C18—C19	1.6 (5)
C4—C5—C6—C1	−0.6 (6)	C17—C18—C19—C14	−0.3 (5)
C2—C1—C6—C5	1.0 (5)	C15—C14—C19—C18	−0.1 (5)
N1—C1—C6—C5	179.6 (3)	N2—C14—C19—C18	179.8 (3)
C1—N1—C7—O1	0.1 (5)	C14—N2—C20—O2	3.4 (5)
C1—N1—C7—C8	−175.7 (3)	C14—N2—C20—C21	−173.0 (3)
O1—C7—C8—C13	−39.9 (4)	O2—C20—C21—C26	−128.9 (3)
N1—C7—C8—C13	135.9 (3)	N2—C20—C21—C26	47.5 (4)
O1—C7—C8—C9	140.8 (3)	O2—C20—C21—C22	48.7 (4)
N1—C7—C8—C9	−43.4 (4)	N2—C20—C21—C22	−134.9 (3)
C13—C8—C9—C10	−1.1 (5)	C26—C21—C22—C23	−1.8 (5)
C7—C8—C9—C10	178.2 (3)	C20—C21—C22—C23	−179.4 (3)
C13—C8—C9—Cl3	175.0 (2)	C26—C21—C22—Cl6	178.6 (2)
C7—C8—C9—Cl3	−5.7 (5)	C20—C21—C22—Cl6	1.0 (4)
C8—C9—C10—C11	0.3 (6)	C21—C22—C23—C24	1.1 (5)
Cl3—C9—C10—C11	−175.8 (3)	Cl6—C22—C23—C24	−179.3 (3)
C9—C10—C11—C12	0.4 (6)	C22—C23—C24—C25	0.6 (6)
C10—C11—C12—C13	−0.3 (6)	C23—C24—C25—C26	−1.7 (6)
C9—C8—C13—C12	1.2 (5)	C24—C25—C26—C21	1.0 (6)
C7—C8—C13—C12	−178.2 (3)	C22—C21—C26—C25	0.7 (5)
C11—C12—C13—C8	−0.5 (6)	C20—C21—C26—C25	178.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.16	2.850 (3)	137
N1—H1N···Cl3	0.86	2.64	3.114 (3)	116
N2—H2N···O1ⁱ	0.86	2.05	2.896 (3)	167

Symmetry code: (i) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₈Cl₃NO
M_r	300.55
Crystal system, space group	Monoclinic, Pc
Temperature (K)	299
a, b, c (Å)	12.310 (1), 7.8307 (6), 14.407 (2)
β (°)	111.52 (1)
V (Å³)	1292.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.75 × 0.75 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.624, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	5882, 3936, 3430
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.104, 1.14
No. of reflections	3936
No. of parameters	326
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28
Absolute structure	(Flack, 1983), 365 Friedel pairs
Absolute structure parameter	0.12 (5)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), 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···O2	0.86	2.16	2.850 (3)	137
N1—H1N···Cl3	0.86	2.64	3.114 (3)	116
N2—H2N···O1ⁱ	0.86	2.05	2.896 (3)	167

Symmetry code: (i) x, −y+1, z−1/2.

Acknowledgements

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

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2007). Acta Cryst. E63, o3789. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar