1-Chloro-methyl-sulfinyl-2-nitro-benzene.

In the title compound, C(7)H(6)ClNO(3)S, the nitro group forms a dihedral angle of 2.7 (4)° with the benzene ring. The bond-angle sum at the S atom is 303.7°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming layers lying parallel to (-101).

Related literature

For the biological and pharmacological activity of sulfoxides, see, for example: Melzig et al. (2009 ▶); Huang et al. (2010 ▶). For related structures, see: Yan (2010 ▶); Kobayashi et al. (2003 ▶).

Experimental

Crystal data

C7H6ClNO3S

M = 219.65

Monoclinic,

a = 12.2394 (5) Å

b = 5.5009 (2) Å

c = 14.5537 (11) Å

β = 116.631 (4)°

V = 875.92 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 180 K

0.23 × 0.20 × 0.18 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.900, T max = 1.000

10209 measured reflections

2172 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.071

S = 1.05

2172 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043553/hb6974sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043553/hb6974Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043553/hb6974Isup3.cml

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

C7H6ClNO3S	F(000) = 448
Mr = 219.65	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6334 reflections
a = 12.2394 (5) Å	θ = 3.3–29.2°
b = 5.5009 (2) Å	µ = 0.65 mm−1
c = 14.5537 (11) Å	T = 180 K
β = 116.631 (4)°	Block, orange
V = 875.92 (9) Å3	0.23 × 0.20 × 0.18 mm
Z = 4

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	2172 independent reflections
Graphite monochromator	1799 reflections with I > 2σ(I)
Detector resolution: 16.1978 pixels mm-1	Rint = 0.024
ω scans	θmax = 29.2°, θmin = 3.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −16→15
Tmin = 0.900, Tmax = 1.000	k = −7→7
10209 measured reflections	l = −19→19

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.1537P] where P = (Fo2 + 2Fc2)/3
2172 reflections	(Δ/σ)max = 0.002
118 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. Absorption correction: Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent, 2011)

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	1.06418 (4)	0.73513 (8)	0.59930 (3)	0.03956 (13)
S1	0.81710 (3)	0.81595 (6)	0.57165 (3)	0.02049 (10)
O1	0.85724 (9)	1.04534 (18)	0.63222 (8)	0.0286 (2)
O11	0.71137 (9)	0.42553 (19)	0.45234 (7)	0.0271 (2)
O12	0.58622 (10)	0.15605 (19)	0.45752 (8)	0.0312 (3)
N1	0.65255 (10)	0.3330 (2)	0.49290 (9)	0.0204 (2)
C1	0.73727 (13)	0.7493 (3)	0.71720 (11)	0.0256 (3)
H1	0.7829	0.8934	0.7453	0.031*
C2	0.67575 (14)	0.6385 (3)	0.76600 (11)	0.0298 (3)
H2	0.6802	0.7065	0.8276	0.036*
C3	0.60801 (13)	0.4300 (3)	0.72587 (11)	0.0290 (3)
H3	0.5672	0.354	0.7604	0.035*
C4	0.59970 (12)	0.3319 (3)	0.63530 (11)	0.0238 (3)
H4	0.5518	0.1908	0.6063	0.029*
C5	0.66235 (12)	0.4428 (2)	0.58775 (10)	0.0186 (3)
C6	0.73266 (11)	0.6514 (2)	0.62775 (10)	0.0188 (3)
C7	0.94884 (12)	0.6136 (3)	0.62770 (11)	0.0231 (3)
H7A	0.9786	0.6027	0.703	0.028*
H7B	0.926	0.4484	0.5982	0.028*

	U11	U22	U33	U12	U13	U23
Cl1	0.0267 (2)	0.0429 (3)	0.0519 (3)	−0.00401 (16)	0.02018 (18)	0.00852 (19)
S1	0.02044 (17)	0.01600 (17)	0.02053 (17)	−0.00089 (12)	0.00517 (13)	0.00213 (13)
O1	0.0302 (5)	0.0156 (5)	0.0326 (5)	−0.0035 (4)	0.0074 (5)	−0.0018 (4)
O11	0.0317 (5)	0.0286 (6)	0.0247 (5)	−0.0052 (4)	0.0161 (4)	−0.0025 (4)
O12	0.0313 (6)	0.0277 (6)	0.0311 (6)	−0.0120 (4)	0.0109 (5)	−0.0111 (5)
N1	0.0192 (5)	0.0183 (6)	0.0205 (5)	0.0001 (4)	0.0061 (5)	−0.0008 (4)
C1	0.0237 (7)	0.0241 (7)	0.0235 (7)	0.0014 (6)	0.0057 (6)	−0.0049 (6)
C2	0.0300 (8)	0.0382 (9)	0.0207 (7)	0.0071 (6)	0.0110 (6)	−0.0023 (6)
C3	0.0263 (7)	0.0370 (9)	0.0270 (7)	0.0044 (6)	0.0148 (6)	0.0079 (7)
C4	0.0210 (7)	0.0228 (7)	0.0271 (7)	0.0004 (5)	0.0103 (6)	0.0032 (6)
C5	0.0171 (6)	0.0184 (6)	0.0178 (6)	0.0033 (5)	0.0054 (5)	0.0006 (5)
C6	0.0177 (6)	0.0171 (6)	0.0192 (6)	0.0033 (5)	0.0061 (5)	0.0022 (5)
C7	0.0191 (6)	0.0206 (6)	0.0279 (7)	0.0001 (5)	0.0091 (5)	0.0043 (6)

Cl1—C7	1.7703 (14)	C2—C3	1.382 (2)
S1—O1	1.4908 (10)	C2—H2	0.95
S1—C6	1.8196 (14)	C3—C4	1.385 (2)
S1—C7	1.8236 (14)	C3—H3	0.95
O11—N1	1.2276 (15)	C4—C5	1.3837 (19)
O12—N1	1.2234 (15)	C4—H4	0.95
N1—C5	1.4618 (17)	C5—C6	1.3953 (18)
C1—C2	1.386 (2)	C7—H7A	0.99
C1—C6	1.3865 (19)	C7—H7B	0.99
C1—H1	0.95
O1—S1—C6	104.99 (6)	C5—C4—C3	118.91 (13)
O1—S1—C7	105.15 (6)	C5—C4—H4	120.5
C6—S1—C7	93.53 (6)	C3—C4—H4	120.5
O12—N1—O11	123.31 (12)	C4—C5—C6	122.02 (12)
O12—N1—C5	118.97 (11)	C4—C5—N1	117.44 (12)
O11—N1—C5	117.72 (11)	C6—C5—N1	120.53 (12)
C2—C1—C6	120.49 (14)	C1—C6—C5	117.97 (13)
C2—C1—H1	119.8	C1—C6—S1	115.84 (11)
C6—C1—H1	119.8	C5—C6—S1	126.16 (10)
C3—C2—C1	120.60 (13)	Cl1—C7—S1	107.62 (7)
C3—C2—H2	119.7	Cl1—C7—H7A	110.2
C1—C2—H2	119.7	S1—C7—H7A	110.2
C2—C3—C4	119.97 (13)	Cl1—C7—H7B	110.2
C2—C3—H3	120	S1—C7—H7B	110.2
C4—C3—H3	120	H7A—C7—H7B	108.5
C6—C1—C2—C3	−0.6 (2)	C4—C5—C6—C1	−0.9 (2)
C1—C2—C3—C4	−0.9 (2)	N1—C5—C6—C1	179.16 (12)
C2—C3—C4—C5	1.5 (2)	C4—C5—C6—S1	−179.03 (10)
C3—C4—C5—C6	−0.6 (2)	N1—C5—C6—S1	1.02 (18)
C3—C4—C5—N1	179.38 (12)	O1—S1—C6—C1	−8.09 (12)
O12—N1—C5—C4	3.01 (18)	C7—S1—C6—C1	98.62 (11)
O11—N1—C5—C4	−177.48 (12)	O1—S1—C6—C5	170.09 (11)
O12—N1—C5—C6	−177.04 (12)	C7—S1—C6—C5	−83.20 (12)
O11—N1—C5—C6	2.47 (18)	O1—S1—C7—Cl1	−67.86 (9)
C2—C1—C6—C5	1.4 (2)	C6—S1—C7—Cl1	−174.44 (8)
C2—C1—C6—S1	179.78 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O12i	0.95	2.44	3.384 (2)	173
C7—H7A···O1ii	0.99	2.36	3.2478 (18)	149
C7—H7B···O1iii	0.99	2.50	3.332 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O12i	0.95	2.44	3.384 (2)	173
C7—H7A⋯O1ii	0.99	2.36	3.2478 (18)	149
C7—H7B⋯O1iii	0.99	2.50	3.332 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) .