2-Chloro-N-(4-chloro-3-iodo-phen-yl)-4-(methyl-sulfon-yl)benzamide.

In the title compound, C(14)H(10)Cl(2)INO(3)S, the dihedral angle between the benzene rings is 52.13 (10)°. In the crystal, the components are linked by pairs of N-H⋯O(sulfon-yl) hydrogen bonds into centrosymmetric dimers.

Related literature

For background to benzamides, see: Castanedo et al. (2010 ▶); Tremblay et al. (2010 ▶); Mahindroo et al. (2010 ▶). For the preparation of the title compound, see: Robarge et al. (2009 ▶).

Experimental

Crystal data

C14H10Cl2INO3S

M = 470.09

Triclinic,

a = 8.8694 (6) Å

b = 10.3837 (8) Å

c = 10.4288 (5) Å

α = 103.862 (5)°

β = 96.452 (5)°

γ = 114.949 (7)°

V = 820.25 (9) Å3

Z = 2

Mo Kα radiation

μ = 2.41 mm−1

T = 290 K

0.30 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.887, T max = 1.000

6770 measured reflections

3323 independent reflections

2957 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.067

S = 1.07

3323 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053633/tk5034sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053633/tk5034Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053633/tk5034Isup3.cml

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

C14H10Cl2INO3S	Z = 2
Mr = 470.09	F(000) = 456
Triclinic, P1	Dx = 1.903 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 8.8694 (6) Å	Cell parameters from 2872 reflections
b = 10.3837 (8) Å	θ = 2.9–26.3°
c = 10.4288 (5) Å	µ = 2.41 mm−1
α = 103.862 (5)°	T = 290 K
β = 96.452 (5)°	Block, colourless
γ = 114.949 (7)°	0.30 × 0.30 × 0.25 mm
V = 820.25 (9) Å3

Oxford Diffraction Xcalibur Eos diffractometer	3323 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2957 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −12→12
Tmin = 0.887, Tmax = 1.000	l = −12→13
6770 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0257P)2 + 0.4057P] where P = (Fo2 + 2Fc2)/3
3323 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

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
I1	0.61447 (3)	0.68561 (3)	0.77089 (2)	0.04648 (9)
Cl1	0.29725 (14)	0.32782 (12)	0.59427 (9)	0.0627 (3)
Cl2	0.29306 (15)	0.99624 (11)	1.34350 (10)	0.0603 (3)
S2	0.11153 (10)	0.80692 (9)	1.76536 (8)	0.03759 (19)
O1	0.4697 (3)	0.8156 (3)	1.2278 (2)	0.0620 (8)
O2	0.0367 (3)	0.6656 (3)	1.7893 (2)	0.0536 (7)
O3	0.0121 (4)	0.8840 (4)	1.7587 (3)	0.0676 (8)
N1	0.2439 (3)	0.5816 (3)	1.1495 (2)	0.0344 (6)
H1	0.1576	0.5214	1.1721	0.041*
C1	0.4083 (4)	0.5502 (4)	0.8367 (3)	0.0328 (7)
C2	0.2898 (4)	0.4068 (4)	0.7585 (3)	0.0390 (8)
C3	0.1603 (4)	0.3219 (4)	0.8106 (3)	0.0478 (9)
H3	0.0821	0.2240	0.7588	0.057*
C4	0.1467 (4)	0.3817 (4)	0.9391 (3)	0.0412 (8)
H4	0.0578	0.3246	0.9729	0.049*
C5	0.2643 (4)	0.5261 (3)	1.0182 (3)	0.0303 (6)
C6	0.3978 (4)	0.6101 (3)	0.9675 (3)	0.0326 (7)
H6	0.4798	0.7061	1.0210	0.039*
C7	0.3431 (4)	0.7173 (4)	1.2433 (3)	0.0370 (7)
C8	0.2843 (4)	0.7407 (3)	1.3728 (3)	0.0315 (7)
C9	0.2612 (4)	0.8646 (3)	1.4266 (3)	0.0346 (7)
C10	0.2081 (4)	0.8860 (3)	1.5459 (3)	0.0346 (7)
H10	0.1917	0.9691	1.5806	0.042*
C11	0.1800 (3)	0.7808 (3)	1.6127 (3)	0.0307 (6)
C12	0.2046 (4)	0.6571 (3)	1.5633 (3)	0.0332 (7)
H12	0.1865	0.5880	1.6099	0.040*
C13	0.2566 (4)	0.6382 (4)	1.4433 (3)	0.0336 (7)
H13	0.2734	0.5553	1.4090	0.040*
C14	0.3027 (5)	0.9225 (5)	1.8925 (3)	0.0601 (11)
H14A	0.2762	0.9474	1.9789	0.090*
H14B	0.3667	1.0126	1.8717	0.090*
H14C	0.3697	0.8705	1.8963	0.090*

	U11	U22	U33	U12	U13	U23
I1	0.05672 (15)	0.05233 (16)	0.04928 (15)	0.02995 (12)	0.03477 (12)	0.02942 (12)
Cl1	0.0823 (7)	0.0685 (7)	0.0327 (4)	0.0349 (6)	0.0224 (5)	0.0051 (4)
Cl2	0.0951 (7)	0.0446 (5)	0.0564 (5)	0.0341 (5)	0.0333 (5)	0.0322 (4)
S2	0.0338 (4)	0.0384 (4)	0.0326 (4)	0.0090 (3)	0.0162 (3)	0.0088 (3)
O1	0.0644 (16)	0.0378 (14)	0.0517 (15)	−0.0044 (13)	0.0346 (13)	0.0034 (12)
O2	0.0539 (14)	0.0436 (15)	0.0454 (13)	0.0031 (12)	0.0266 (12)	0.0140 (11)
O3	0.0703 (18)	0.094 (2)	0.0684 (18)	0.0555 (18)	0.0411 (15)	0.0315 (16)
N1	0.0369 (13)	0.0297 (14)	0.0319 (13)	0.0082 (11)	0.0193 (11)	0.0108 (11)
C1	0.0395 (16)	0.0390 (18)	0.0308 (15)	0.0225 (14)	0.0159 (13)	0.0181 (14)
C2	0.0490 (18)	0.048 (2)	0.0240 (15)	0.0270 (17)	0.0120 (14)	0.0086 (14)
C3	0.0491 (19)	0.040 (2)	0.0351 (18)	0.0103 (17)	0.0068 (15)	0.0020 (15)
C4	0.0386 (16)	0.0398 (19)	0.0350 (17)	0.0075 (15)	0.0120 (14)	0.0134 (14)
C5	0.0358 (15)	0.0330 (16)	0.0258 (14)	0.0157 (13)	0.0129 (12)	0.0134 (12)
C6	0.0356 (15)	0.0292 (16)	0.0325 (15)	0.0128 (13)	0.0116 (13)	0.0117 (13)
C7	0.0403 (17)	0.0300 (17)	0.0345 (16)	0.0089 (14)	0.0156 (14)	0.0107 (14)
C8	0.0283 (14)	0.0296 (16)	0.0300 (15)	0.0065 (13)	0.0098 (12)	0.0104 (13)
C9	0.0421 (16)	0.0282 (16)	0.0324 (15)	0.0126 (14)	0.0123 (14)	0.0135 (13)
C10	0.0367 (16)	0.0297 (16)	0.0345 (16)	0.0132 (14)	0.0105 (13)	0.0083 (13)
C11	0.0267 (13)	0.0341 (17)	0.0260 (14)	0.0092 (13)	0.0078 (12)	0.0092 (12)
C12	0.0357 (15)	0.0314 (17)	0.0337 (15)	0.0135 (13)	0.0122 (13)	0.0147 (13)
C13	0.0390 (16)	0.0320 (17)	0.0332 (16)	0.0178 (14)	0.0142 (13)	0.0112 (13)
C14	0.056 (2)	0.051 (2)	0.0362 (19)	−0.0018 (19)	0.0054 (17)	0.0050 (17)

I1—C1	2.090 (3)	C4—C5	1.382 (4)
Cl1—C2	1.735 (3)	C5—C6	1.391 (4)
Cl2—C9	1.731 (3)	C6—H6	0.9300
S2—O2	1.431 (3)	C7—C8	1.504 (4)
S2—O3	1.426 (3)	C8—C9	1.384 (4)
S2—C11	1.769 (3)	C8—C13	1.388 (4)
S2—C14	1.757 (4)	C9—C10	1.381 (4)
O1—C7	1.218 (4)	C10—H10	0.9300
N1—H1	0.8600	C10—C11	1.383 (4)
N1—C5	1.416 (4)	C11—C12	1.380 (4)
N1—C7	1.348 (4)	C12—H12	0.9300
C1—C2	1.375 (5)	C12—C13	1.381 (4)
C1—C6	1.388 (4)	C13—H13	0.9300
C2—C3	1.381 (5)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C3—C4	1.378 (4)	C14—H14C	0.9600
C4—H4	0.9300
O2—S2—C11	107.98 (15)	O1—C7—N1	124.5 (3)
O2—S2—C14	106.74 (19)	O1—C7—C8	121.2 (3)
O3—S2—O2	118.76 (18)	N1—C7—C8	114.3 (2)
O3—S2—C11	108.53 (16)	C9—C8—C7	121.8 (3)
O3—S2—C14	109.7 (2)	C9—C8—C13	118.5 (3)
C14—S2—C11	104.21 (16)	C13—C8—C7	119.7 (3)
C5—N1—H1	116.0	C8—C9—Cl2	120.7 (2)
C7—N1—H1	116.0	C10—C9—Cl2	117.7 (3)
C7—N1—C5	128.0 (2)	C10—C9—C8	121.6 (3)
C2—C1—I1	123.1 (2)	C9—C10—H10	120.8
C2—C1—C6	120.3 (3)	C9—C10—C11	118.4 (3)
C6—C1—I1	116.6 (2)	C11—C10—H10	120.8
C1—C2—Cl1	121.8 (2)	C10—C11—S2	118.7 (2)
C1—C2—C3	119.8 (3)	C12—C11—S2	119.6 (2)
C3—C2—Cl1	118.3 (3)	C12—C11—C10	121.7 (3)
C2—C3—H3	119.9	C11—C12—H12	120.7
C4—C3—C2	120.3 (3)	C11—C12—C13	118.6 (3)
C4—C3—H3	119.9	C13—C12—H12	120.7
C3—C4—H4	119.8	C8—C13—H13	119.4
C3—C4—C5	120.4 (3)	C12—C13—C8	121.3 (3)
C5—C4—H4	119.8	C12—C13—H13	119.4
C4—C5—N1	117.9 (3)	S2—C14—H14A	109.5
C4—C5—C6	119.4 (3)	S2—C14—H14B	109.5
C6—C5—N1	122.7 (3)	S2—C14—H14C	109.5
C1—C6—C5	119.8 (3)	H14A—C14—H14B	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
C5—C6—H6	120.1	H14B—C14—H14C	109.5
I1—C1—C2—Cl1	−2.5 (4)	C4—C5—C6—C1	2.2 (5)
I1—C1—C2—C3	177.7 (3)	C5—N1—C7—O1	0.1 (6)
I1—C1—C6—C5	−179.8 (2)	C5—N1—C7—C8	179.6 (3)
Cl1—C2—C3—C4	−178.1 (3)	C6—C1—C2—Cl1	179.6 (2)
Cl2—C9—C10—C11	179.2 (2)	C6—C1—C2—C3	−0.2 (5)
S2—C11—C12—C13	179.4 (2)	C7—N1—C5—C4	179.5 (3)
O1—C7—C8—C9	51.1 (5)	C7—N1—C5—C6	0.2 (5)
O1—C7—C8—C13	−127.0 (4)	C7—C8—C9—Cl2	2.0 (4)
O2—S2—C11—C10	160.6 (2)	C7—C8—C9—C10	−179.6 (3)
O2—S2—C11—C12	−19.6 (3)	C7—C8—C13—C12	179.2 (3)
O3—S2—C11—C10	30.7 (3)	C8—C9—C10—C11	0.8 (5)
O3—S2—C11—C12	−149.6 (3)	C9—C8—C13—C12	1.0 (4)
N1—C5—C6—C1	−178.5 (3)	C9—C10—C11—S2	−179.9 (2)
N1—C7—C8—C9	−128.4 (3)	C9—C10—C11—C12	0.4 (4)
N1—C7—C8—C13	53.5 (4)	C10—C11—C12—C13	−0.8 (4)
C1—C2—C3—C4	1.8 (6)	C11—C12—C13—C8	0.1 (4)
C2—C1—C6—C5	−1.7 (5)	C13—C8—C9—Cl2	−179.8 (2)
C2—C3—C4—C5	−1.3 (6)	C13—C8—C9—C10	−1.5 (4)
C3—C4—C5—N1	−180.0 (3)	C14—S2—C11—C10	−86.2 (3)
C3—C4—C5—C6	−0.7 (5)	C14—S2—C11—C12	93.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.15	2.991 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.15	2.991 (3)	167

Symmetry code: (i) .