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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048987/rz2093sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048987/rz2093Isup2.hkl
Contains datablock I

CCDC reference: 630230

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

Computing details top

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 top
Crystal data top
C7H6ClNO4SZ = 2
Mr = 235.65F(000) = 240
Triclinic, P1Dx = 1.718 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9754 (11) ÅCell parameters from 1520 reflections
b = 8.2311 (13) Åθ = 2.7–24.9°
c = 8.7890 (14) ŵ = 0.63 mm1
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) Å3
Data collection top
Bruker APEX area-detector
diffractometer
1651 independent reflections
Radiation source: fine-focus sealed tube1566 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
φ and ω scansθmax = 25.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 88
Tmin = 0.833, Tmax = 0.916k = 99
3381 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0493P)2 + 0.2421P]
where P = (Fo2 + 2Fc2)/3
1651 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl11.41149 (9)0.82911 (8)0.49187 (7)0.0480 (2)
S10.62527 (8)0.71208 (7)0.86507 (6)0.03577 (18)
O10.4489 (2)0.8799 (2)0.8790 (2)0.0490 (4)
O20.6174 (3)0.5657 (2)0.7831 (2)0.0497 (4)
O30.9672 (3)1.1725 (2)0.8778 (2)0.0611 (5)
O41.1422 (3)1.1632 (2)0.6476 (2)0.0623 (5)
N11.0534 (3)1.1006 (2)0.7483 (2)0.0399 (5)
C10.8551 (3)0.7433 (3)0.7706 (2)0.0307 (4)
C20.8730 (3)0.9012 (3)0.7978 (2)0.0322 (5)
H20.77110.98700.87070.039*
C31.0447 (3)0.9295 (3)0.7148 (2)0.0308 (4)
C41.1978 (3)0.8021 (3)0.6045 (2)0.0327 (5)
C51.1800 (4)0.6422 (3)0.5844 (3)0.0387 (5)
H51.28390.55410.51430.046*
C61.0101 (3)0.6124 (3)0.6671 (3)0.0362 (5)
H60.99980.50450.65340.043*
C70.6707 (5)0.6511 (4)1.0508 (3)0.0563 (7)
H7A0.69430.74201.10200.085*
H7B0.79340.54211.04240.085*
H7C0.54920.63571.10990.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0409 (3)0.0535 (4)0.0499 (4)0.0263 (3)0.0077 (3)0.0030 (3)
S10.0351 (3)0.0426 (3)0.0369 (3)0.0253 (3)0.0020 (2)0.0004 (2)
O10.0328 (8)0.0543 (10)0.0574 (11)0.0182 (8)0.0001 (7)0.0059 (8)
O20.0556 (10)0.0533 (10)0.0531 (10)0.0394 (9)0.0005 (8)0.0063 (8)
O30.0725 (13)0.0460 (10)0.0672 (13)0.0340 (10)0.0059 (10)0.0173 (9)
O40.0698 (12)0.0421 (10)0.0788 (13)0.0351 (9)0.0052 (10)0.0097 (9)
N10.0367 (10)0.0298 (9)0.0560 (12)0.0174 (8)0.0065 (9)0.0027 (9)
C10.0311 (10)0.0317 (10)0.0324 (10)0.0169 (9)0.0035 (8)0.0026 (8)
C20.0297 (10)0.0300 (10)0.0360 (11)0.0127 (8)0.0016 (8)0.0018 (8)
C30.0319 (10)0.0275 (10)0.0359 (11)0.0147 (8)0.0070 (8)0.0037 (8)
C40.0289 (10)0.0378 (11)0.0326 (11)0.0158 (9)0.0029 (8)0.0045 (9)
C50.0355 (11)0.0351 (11)0.0420 (12)0.0144 (9)0.0023 (9)0.0070 (9)
C60.0396 (12)0.0295 (11)0.0421 (12)0.0179 (9)0.0048 (9)0.0008 (9)
C70.0653 (17)0.0808 (19)0.0421 (14)0.0497 (16)0.0101 (12)0.0165 (13)
Geometric parameters (Å, º) top
Cl1—C41.719 (2)C2—C31.382 (3)
S1—O11.4347 (18)C2—H20.9300
S1—O21.4358 (17)C3—C41.395 (3)
S1—C71.751 (3)C4—C51.386 (3)
S1—C11.774 (2)C5—C61.377 (3)
O3—N11.221 (3)C5—H50.9300
O4—N11.211 (3)C6—H60.9300
N1—C31.469 (3)C7—H7A0.9600
C1—C61.380 (3)C7—H7B0.9600
C1—C21.381 (3)C7—H7C0.9600
O1—S1—O2118.60 (11)C4—C3—N1122.74 (18)
O1—S1—C7108.83 (13)C5—C4—C3118.65 (19)
O2—S1—C7108.71 (13)C5—C4—Cl1117.23 (16)
O1—S1—C1107.51 (10)C3—C4—Cl1124.12 (17)
O2—S1—C1107.25 (10)C6—C5—C4120.7 (2)
C7—S1—C1105.12 (11)C6—C5—H5119.7
O4—N1—O3123.74 (19)C4—C5—H5119.7
O4—N1—C3119.2 (2)C5—C6—C1119.76 (19)
O3—N1—C3117.09 (18)C5—C6—H6120.1
C6—C1—C2120.85 (19)C1—C6—H6120.1
C6—C1—S1119.76 (15)S1—C7—H7A109.5
C2—C1—S1119.36 (16)S1—C7—H7B109.5
C1—C2—C3118.92 (19)H7A—C7—H7B109.5
C1—C2—H2120.5S1—C7—H7C109.5
C3—C2—H2120.5H7A—C7—H7C109.5
C2—C3—C4121.04 (19)H7B—C7—H7C109.5
C2—C3—N1116.21 (18)
O1—S1—C1—C6143.50 (18)O4—N1—C3—C427.3 (3)
O2—S1—C1—C614.9 (2)O3—N1—C3—C4153.4 (2)
C7—S1—C1—C6100.7 (2)C2—C3—C4—C52.9 (3)
O1—S1—C1—C234.3 (2)N1—C3—C4—C5177.93 (19)
O2—S1—C1—C2162.85 (17)C2—C3—C4—Cl1177.86 (16)
C7—S1—C1—C281.6 (2)N1—C3—C4—Cl11.3 (3)
C6—C1—C2—C32.7 (3)C3—C4—C5—C62.6 (3)
S1—C1—C2—C3175.10 (15)Cl1—C4—C5—C6178.17 (18)
C1—C2—C3—C40.4 (3)C4—C5—C6—C10.3 (4)
C1—C2—C3—N1179.54 (18)C2—C1—C6—C53.0 (3)
O4—N1—C3—C2151.9 (2)S1—C1—C6—C5174.72 (17)
O3—N1—C3—C227.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O20.932.552.909 (3)103
C2—H2···O1i0.932.433.309 (2)159
C6—H6···O4ii0.932.593.442 (3)153
C7—H7C···O2iii0.962.463.316 (4)149
Symmetry codes: (i) x+1, y+2, z+2; (ii) x, y1, z; (iii) x+1, y+1, z+2.
 

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