4-Chloro-3-nitro­phenyl methyl sulfone

In the title compound, C₇H₆ClNO₄S, the average S—C and S=O bond lengths are 1.762 (3) and 1.4352 (18) Å, respectively. In the crystal packing, the mol­ecules are linked by inter­molecular C—H...O hydrogen bonds to form layers parallel to the (101) plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O4      ..       3.15 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

4-Chloro-3-nitrophenyl methyl sulfone

Crystal data

C7H6ClNO4S	Z = 2
Mr = 235.65	F(000) = 240
Triclinic, P1	Dx = 1.718 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9754 (11) Å	Cell parameters from 1520 reflections
b = 8.2311 (13) Å	θ = 2.7–24.9°
c = 8.7890 (14) Å	µ = 0.63 mm^−1
α = 89.296 (2)°	T = 298 K
β = 79.266 (2)°	Block, colourless
γ = 67.020 (2)°	0.34 × 0.15 × 0.14 mm
V = 455.43 (12) Å^3

Data collection

Bruker APEX area-detector diffractometer	1651 independent reflections
Radiation source: fine-focus sealed tube	1566 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.833, Tmax = 0.916	k = −9→9
3381 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.2421P] where P = (Fo^2 + 2Fc^2)/3
1651 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, p.p.m.): δ 8.46 (m, 1H), 8.08–8.11 (m, 1H), 7.83 (d, 1H), 3.14 (s, 3H).

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.41149 (9)	0.82911 (8)	0.49187 (7)	0.0480 (2)
S1	0.62527 (8)	0.71208 (7)	0.86507 (6)	0.03577 (18)
O1	0.4489 (2)	0.8799 (2)	0.8790 (2)	0.0490 (4)
O2	0.6174 (3)	0.5657 (2)	0.7831 (2)	0.0497 (4)
O3	0.9672 (3)	1.1725 (2)	0.8778 (2)	0.0611 (5)
O4	1.1422 (3)	1.1632 (2)	0.6476 (2)	0.0623 (5)
N1	1.0534 (3)	1.1006 (2)	0.7483 (2)	0.0399 (5)
C1	0.8551 (3)	0.7433 (3)	0.7706 (2)	0.0307 (4)
C2	0.8730 (3)	0.9012 (3)	0.7978 (2)	0.0322 (5)
H2	0.7711	0.9870	0.8707	0.039*
C3	1.0447 (3)	0.9295 (3)	0.7148 (2)	0.0308 (4)
C4	1.1978 (3)	0.8021 (3)	0.6045 (2)	0.0327 (5)
C5	1.1800 (4)	0.6422 (3)	0.5844 (3)	0.0387 (5)
H5	1.2839	0.5541	0.5143	0.046*
C6	1.0101 (3)	0.6124 (3)	0.6671 (3)	0.0362 (5)
H6	0.9998	0.5045	0.6534	0.043*
C7	0.6707 (5)	0.6511 (4)	1.0508 (3)	0.0563 (7)
H7A	0.6943	0.7420	1.1020	0.085*
H7B	0.7934	0.5421	1.0424	0.085*
H7C	0.5492	0.6357	1.1099	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0409 (3)	0.0535 (4)	0.0499 (4)	−0.0263 (3)	0.0077 (3)	0.0030 (3)
S1	0.0351 (3)	0.0426 (3)	0.0369 (3)	−0.0253 (3)	−0.0020 (2)	−0.0004 (2)
O1	0.0328 (8)	0.0543 (10)	0.0574 (11)	−0.0182 (8)	0.0001 (7)	−0.0059 (8)
O2	0.0556 (10)	0.0533 (10)	0.0531 (10)	−0.0394 (9)	−0.0005 (8)	−0.0063 (8)
O3	0.0725 (13)	0.0460 (10)	0.0672 (13)	−0.0340 (10)	0.0059 (10)	−0.0173 (9)
O4	0.0698 (12)	0.0421 (10)	0.0788 (13)	−0.0351 (9)	0.0052 (10)	0.0097 (9)
N1	0.0367 (10)	0.0298 (9)	0.0560 (12)	−0.0174 (8)	−0.0065 (9)	0.0027 (9)
C1	0.0311 (10)	0.0317 (10)	0.0324 (10)	−0.0169 (9)	−0.0035 (8)	0.0026 (8)
C2	0.0297 (10)	0.0300 (10)	0.0360 (11)	−0.0127 (8)	−0.0016 (8)	−0.0018 (8)
C3	0.0319 (10)	0.0275 (10)	0.0359 (11)	−0.0147 (8)	−0.0070 (8)	0.0037 (8)
C4	0.0289 (10)	0.0378 (11)	0.0326 (11)	−0.0158 (9)	−0.0029 (8)	0.0045 (9)
C5	0.0355 (11)	0.0351 (11)	0.0420 (12)	−0.0144 (9)	0.0023 (9)	−0.0070 (9)
C6	0.0396 (12)	0.0295 (11)	0.0421 (12)	−0.0179 (9)	−0.0048 (9)	−0.0008 (9)
C7	0.0653 (17)	0.0808 (19)	0.0421 (14)	−0.0497 (16)	−0.0101 (12)	0.0165 (13)

Geometric parameters (Å, º)

Cl1—C4	1.719 (2)	C2—C3	1.382 (3)
S1—O1	1.4347 (18)	C2—H2	0.9300
S1—O2	1.4358 (17)	C3—C4	1.395 (3)
S1—C7	1.751 (3)	C4—C5	1.386 (3)
S1—C1	1.774 (2)	C5—C6	1.377 (3)
O3—N1	1.221 (3)	C5—H5	0.9300
O4—N1	1.211 (3)	C6—H6	0.9300
N1—C3	1.469 (3)	C7—H7A	0.9600
C1—C6	1.380 (3)	C7—H7B	0.9600
C1—C2	1.381 (3)	C7—H7C	0.9600
O1—S1—O2	118.60 (11)	C4—C3—N1	122.74 (18)
O1—S1—C7	108.83 (13)	C5—C4—C3	118.65 (19)
O2—S1—C7	108.71 (13)	C5—C4—Cl1	117.23 (16)
O1—S1—C1	107.51 (10)	C3—C4—Cl1	124.12 (17)
O2—S1—C1	107.25 (10)	C6—C5—C4	120.7 (2)
C7—S1—C1	105.12 (11)	C6—C5—H5	119.7
O4—N1—O3	123.74 (19)	C4—C5—H5	119.7
O4—N1—C3	119.2 (2)	C5—C6—C1	119.76 (19)
O3—N1—C3	117.09 (18)	C5—C6—H6	120.1
C6—C1—C2	120.85 (19)	C1—C6—H6	120.1
C6—C1—S1	119.76 (15)	S1—C7—H7A	109.5
C2—C1—S1	119.36 (16)	S1—C7—H7B	109.5
C1—C2—C3	118.92 (19)	H7A—C7—H7B	109.5
C1—C2—H2	120.5	S1—C7—H7C	109.5
C3—C2—H2	120.5	H7A—C7—H7C	109.5
C2—C3—C4	121.04 (19)	H7B—C7—H7C	109.5
C2—C3—N1	116.21 (18)
O1—S1—C1—C6	−143.50 (18)	O4—N1—C3—C4	27.3 (3)
O2—S1—C1—C6	−14.9 (2)	O3—N1—C3—C4	−153.4 (2)
C7—S1—C1—C6	100.7 (2)	C2—C3—C4—C5	−2.9 (3)
O1—S1—C1—C2	34.3 (2)	N1—C3—C4—C5	177.93 (19)
O2—S1—C1—C2	162.85 (17)	C2—C3—C4—Cl1	177.86 (16)
C7—S1—C1—C2	−81.6 (2)	N1—C3—C4—Cl1	−1.3 (3)
C6—C1—C2—C3	2.7 (3)	C3—C4—C5—C6	2.6 (3)
S1—C1—C2—C3	−175.10 (15)	Cl1—C4—C5—C6	−178.17 (18)
C1—C2—C3—C4	0.4 (3)	C4—C5—C6—C1	0.3 (4)
C1—C2—C3—N1	179.54 (18)	C2—C1—C6—C5	−3.0 (3)
O4—N1—C3—C2	−151.9 (2)	S1—C1—C6—C5	174.72 (17)
O3—N1—C3—C2	27.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.55	2.909 (3)	103
C2—H2···O1^i	0.93	2.43	3.309 (2)	159
C6—H6···O4^ii	0.93	2.59	3.442 (3)	153
C7—H7C···O2^iii	0.96	2.46	3.316 (4)	149

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+2.