2-Chloro-N-(2,3-dichloro-phen-yl)benzamide.

Two independent mol-ecules comprise the asymmetric unit in the title compound, C(13)H(8)Cl(3)NO, each with the amide N-H and C=O bonds trans to each other. The mol-ecules are linked into chains through inter-molecular 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 = 300.55

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.104

S = 1.14

3936 reflections

326 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: (Flack, 1983 ▶), 365 Friedel pairs

Flack parameter: 0.12 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018679/tk2277sup1.cif

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

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

C13H8Cl3NO	F000 = 608
Mr = 300.55	Dx = 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 = 2.6–27.5º
b = 7.8307 (6) Å	µ = 0.69 mm−1
c = 14.407 (2) Å	T = 299 (2) K
β = 111.52 (1)º	Thick plate, colourless
V = 1292.0 (2) Å3	0.75 × 0.75 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3936 independent reflections
Radiation source: fine-focus sealed tube	3430 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.014
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.6º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −15→13
Tmin = 0.624, Tmax = 0.885	k = −9→9
5882 measured reflections	l = −15→18

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(Fo2) + (0.0715P)2 + 0.0104P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104	(Δ/σ)max = 0.003
S = 1.14	Δρmax = 0.29 e Å−3
3936 reflections	Δρmin = −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	Flack parameter: 0.12 (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
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*

	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)

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)

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

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) .