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ISSN: 2056-9890

N-[(4-Chloro­phen­yl)sulfon­yl]acetamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, St. Joseph Engineering College, Vamanjoor, Mangalore 575 028, Karnataka, India
*Correspondence e-mail: hkfun@usm.my

(Received 26 July 2012; accepted 27 July 2012; online 4 August 2012)

The asymmetric unit of the title compound, C8H8ClNO3S, consists of two crystallographically independent mol­ecules (A and B). The dihedral angles between the benzene ring and amide C—C(=O)—NH– plane are 87.6 (3) (mol­ecule A) and 86.0 (3)° (mol­ecule B). In the crystal, the independent mol­ecules are alternately linked by N—H⋯O hydrogen bonds into an infinite chain along the b axis. Short inter­molecular Cl⋯Cl contacts [3.2882 (5) and 3.2812 (5) Å] are also observed.

Related literature

For a related structure, see: Fun et al. (2012[Fun, H.-K., Chia, T. S., Hegde, P., Jyothi, K. & D'Souza, P. R. (2012). Acta Cryst. E68, o2025.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8ClNO3S

  • Mr = 233.66

  • Monoclinic, P 2/c

  • a = 12.1801 (6) Å

  • b = 9.2529 (4) Å

  • c = 17.6769 (8) Å

  • β = 101.979 (1)°

  • V = 1948.83 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.59 mm−1

  • T = 100 K

  • 0.36 × 0.14 × 0.14 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.819, Tmax = 0.923

  • 45479 measured reflections

  • 7130 independent reflections

  • 5439 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.090

  • S = 1.04

  • 7130 reflections

  • 263 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1B—H1NB⋯O3Ai 0.871 (15) 1.939 (15) 2.7980 (10) 168.6 (13)
N1A—H1NA⋯O3Bii 0.865 (15) 1.939 (15) 2.7952 (10) 170.0 (13)
Symmetry codes: (i) x+1, y+1, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In continuation to our reports on the biological activity of sulfonamide containing compounds (Fun et al., 2012), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules (A and B). The C O and N—H bonds in the amide planes [C7A/O3A/N1A/H1NA and C7B/O3B/N1B/H1NB; maximum deviations = 0.043 (5) Å at atom N1A and 0.047 (5) Å at atom H1NB] are trans to each other. The benzene ring (C1–C6) forms a dihedral angle of 87.6 (3)° with the amide plane in molecule A, whereas the corresponding angle is 86.0 (3)° in molecule B. The bond lengths and angles are comparable to those found in a related structure (Fun et al., 2012). In the crystal (Fig. 2), molecules are linked by intermolecular N1B—H1NB···O3A and N1A—H1NA···O3B hydrogen bonds (Table 1) into an infinite chain along the b axis. Short intermolecular Cl1A···Cl1A [3.2882 (5) Å; 1 - x, 1 - y, 1 - z] and Cl1B···Cl1B [3.2812 (5) Å; 1 - x, y, -1/2 - z] are also observed.

Related literature top

For a related structure, see: Fun et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a vigorously stirred mixture of 4-chlorobenzenesulphonamide and silica sulfuric acid, acid chloride or acid anhydride was added at RT. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added and the solid catalyst was removed by filtration. The filtrate was washed with water, dried and evaporated. The crude product was purified by recrystallization from an ethanol solution to yield colourless single crystals of the title compound.

Refinement top

The N-bound H atoms were located in a difference Fourier map and refined freely [N1A—H1NA = 0.865 (14) Å and N1B—H1NB = 0.871 (14) Å]. The remaining H atoms were positioned geometrically (C—H = 0.95 and 0.98 Å) and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl group. Four outliers, (204), (100), (348) and (233), were omitted in the final refinement.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the c axis. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.
N-[(4-Chlorophenyl)sulfonyl]acetamide top
Crystal data top
C8H8ClNO3SF(000) = 960
Mr = 233.66Dx = 1.593 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 9840 reflections
a = 12.1801 (6) Åθ = 2.5–32.6°
b = 9.2529 (4) ŵ = 0.59 mm1
c = 17.6769 (8) ÅT = 100 K
β = 101.979 (1)°Block, colourless
V = 1948.83 (16) Å30.36 × 0.14 × 0.14 mm
Z = 8
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
7130 independent reflections
Radiation source: fine-focus sealed tube5439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 32.7°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1818
Tmin = 0.819, Tmax = 0.923k = 1413
45479 measured reflectionsl = 2626
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0436P)2 + 0.5704P]
where P = (Fo2 + 2Fc2)/3
7130 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C8H8ClNO3SV = 1948.83 (16) Å3
Mr = 233.66Z = 8
Monoclinic, P2/cMo Kα radiation
a = 12.1801 (6) ŵ = 0.59 mm1
b = 9.2529 (4) ÅT = 100 K
c = 17.6769 (8) Å0.36 × 0.14 × 0.14 mm
β = 101.979 (1)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
7130 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5439 reflections with I > 2σ(I)
Tmin = 0.819, Tmax = 0.923Rint = 0.033
45479 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.48 e Å3
7130 reflectionsΔρmin = 0.52 e Å3
263 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1A0.47973 (2)0.51064 (3)0.405269 (18)0.02673 (7)
S1A0.170782 (19)0.51977 (2)0.076741 (14)0.01367 (6)
O1A0.19060 (6)0.64897 (8)0.03653 (4)0.02048 (14)
O2A0.17384 (6)0.38233 (8)0.04030 (4)0.01910 (14)
O3A0.03482 (6)0.33069 (7)0.15483 (4)0.01845 (14)
N1A0.04580 (7)0.54746 (8)0.09688 (5)0.01463 (14)
C1A0.29561 (8)0.64713 (10)0.20474 (6)0.01909 (18)
H1AA0.27120.73620.18020.023*
C2A0.36445 (8)0.64567 (11)0.27788 (6)0.02079 (19)
H2AA0.38790.73350.30420.025*
C3A0.39837 (8)0.51313 (11)0.31194 (6)0.01803 (19)
C4A0.36704 (8)0.38278 (11)0.27505 (6)0.01842 (18)
H4AA0.39260.29390.29940.022*
C5A0.29771 (7)0.38417 (10)0.20193 (6)0.01646 (17)
H5AA0.27450.29620.17570.020*
C6A0.26276 (8)0.51635 (9)0.16772 (6)0.01437 (17)
C7A0.00697 (7)0.44855 (9)0.13606 (5)0.01418 (16)
C8A0.11629 (9)0.49932 (10)0.15322 (7)0.01856 (19)
H8AA0.14110.43140.18880.028*
H8AB0.17290.50440.10500.028*
H8AC0.10620.59530.17710.028*
Cl1B0.52074 (2)0.97797 (3)0.155284 (17)0.02637 (7)
S1B0.82941 (2)1.00993 (2)0.172976 (15)0.01367 (6)
O1B0.80290 (6)1.13770 (8)0.21146 (4)0.01954 (14)
O2B0.83407 (6)0.87333 (8)0.21118 (4)0.01972 (14)
O3B0.97057 (6)0.83316 (7)0.09436 (4)0.01887 (14)
N1B0.95264 (7)1.04795 (8)0.15212 (5)0.01459 (14)
C1B0.69388 (8)1.12533 (10)0.04604 (6)0.01691 (17)
H1BA0.71121.21570.07120.020*
C2B0.62534 (8)1.11904 (10)0.02700 (6)0.01873 (18)
H2BA0.59501.20480.05260.022*
C3B0.60174 (8)0.98501 (11)0.06205 (6)0.01785 (18)
C4B0.64282 (8)0.85698 (11)0.02594 (6)0.01874 (18)
H4BA0.62410.76670.05080.022*
C5B0.71197 (8)0.86331 (10)0.04738 (6)0.01664 (17)
H5BA0.74150.77730.07320.020*
C6B0.73726 (8)0.99763 (9)0.08230 (6)0.01408 (17)
C7B1.00893 (7)0.95272 (9)0.11338 (5)0.01431 (16)
C8B1.11652 (8)1.00994 (10)0.09647 (7)0.01848 (19)
H8BA1.14750.93960.06510.028*
H8BB1.17041.02640.14520.028*
H8BC1.10191.10120.06810.028*
H1NB0.9739 (11)1.1378 (16)0.1584 (8)0.025 (3)*
H1NA0.0217 (11)0.6354 (16)0.0901 (8)0.026 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.02335 (13)0.03545 (14)0.01876 (15)0.00052 (9)0.00167 (10)0.00159 (9)
S1A0.01605 (11)0.01243 (10)0.01325 (12)0.00092 (7)0.00468 (8)0.00067 (7)
O1A0.0248 (3)0.0179 (3)0.0203 (4)0.0010 (3)0.0084 (3)0.0060 (3)
O2A0.0240 (3)0.0163 (3)0.0169 (3)0.0032 (2)0.0043 (3)0.0037 (2)
O3A0.0202 (3)0.0117 (3)0.0232 (4)0.0001 (2)0.0038 (3)0.0033 (2)
N1A0.0165 (3)0.0101 (3)0.0179 (4)0.0015 (2)0.0050 (3)0.0020 (3)
C1A0.0213 (4)0.0135 (4)0.0215 (5)0.0011 (3)0.0024 (4)0.0019 (3)
C2A0.0220 (4)0.0175 (4)0.0219 (5)0.0002 (3)0.0022 (4)0.0048 (3)
C3A0.0146 (4)0.0225 (4)0.0165 (5)0.0007 (3)0.0024 (4)0.0009 (3)
C4A0.0175 (4)0.0177 (4)0.0196 (5)0.0004 (3)0.0027 (3)0.0028 (3)
C5A0.0166 (4)0.0135 (4)0.0190 (4)0.0004 (3)0.0029 (3)0.0010 (3)
C6A0.0148 (4)0.0132 (4)0.0154 (5)0.0002 (3)0.0040 (3)0.0007 (3)
C7A0.0156 (4)0.0129 (4)0.0137 (4)0.0015 (3)0.0023 (3)0.0001 (3)
C8A0.0176 (4)0.0199 (4)0.0196 (5)0.0018 (3)0.0071 (4)0.0023 (3)
Cl1B0.02278 (12)0.03587 (14)0.01794 (14)0.00114 (9)0.00155 (10)0.00122 (9)
S1B0.01612 (11)0.01213 (9)0.01342 (12)0.00106 (7)0.00458 (9)0.00113 (7)
O1B0.0222 (3)0.0182 (3)0.0193 (4)0.0006 (2)0.0067 (3)0.0061 (3)
O2B0.0251 (3)0.0159 (3)0.0181 (3)0.0030 (2)0.0044 (3)0.0039 (2)
O3B0.0216 (3)0.0118 (3)0.0227 (4)0.0011 (2)0.0033 (3)0.0030 (2)
N1B0.0169 (3)0.0099 (3)0.0179 (4)0.0010 (2)0.0055 (3)0.0013 (3)
C1B0.0198 (4)0.0125 (4)0.0187 (4)0.0007 (3)0.0047 (3)0.0005 (3)
C2B0.0192 (4)0.0173 (4)0.0193 (5)0.0000 (3)0.0032 (3)0.0028 (3)
C3B0.0143 (4)0.0227 (4)0.0162 (5)0.0008 (3)0.0024 (4)0.0006 (3)
C4B0.0174 (4)0.0177 (4)0.0203 (5)0.0007 (3)0.0019 (3)0.0051 (3)
C5B0.0167 (4)0.0127 (4)0.0200 (5)0.0001 (3)0.0027 (3)0.0022 (3)
C6B0.0148 (4)0.0125 (4)0.0157 (5)0.0008 (3)0.0048 (4)0.0010 (3)
C7B0.0160 (4)0.0126 (4)0.0140 (4)0.0022 (3)0.0022 (3)0.0004 (3)
C8B0.0172 (4)0.0192 (4)0.0204 (5)0.0004 (3)0.0071 (4)0.0006 (3)
Geometric parameters (Å, º) top
Cl1A—C3A1.7394 (11)Cl1B—C3B1.7375 (11)
S1A—O2A1.4295 (7)S1B—O2B1.4286 (7)
S1A—O1A1.4366 (7)S1B—O1B1.4339 (7)
S1A—N1A1.6537 (8)S1B—N1B1.6559 (8)
S1A—C6A1.7591 (11)S1B—C6B1.7593 (11)
O3A—C7A1.2200 (11)O3B—C7B1.2206 (11)
N1A—C7A1.3839 (11)N1B—C7B1.3823 (11)
N1A—H1NA0.865 (14)N1B—H1NB0.871 (14)
C1A—C2A1.3873 (15)C1B—C2B1.3855 (14)
C1A—C6A1.3943 (13)C1B—C6B1.3949 (13)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—C3A1.3907 (14)C2B—C3B1.3895 (14)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.3864 (14)C3B—C4B1.3887 (14)
C4A—C5A1.3897 (14)C4B—C5B1.3925 (14)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.3913 (13)C5B—C6B1.3934 (12)
C5A—H5AA0.9500C5B—H5BA0.9500
C7A—C8A1.5012 (13)C7B—C8B1.4998 (13)
C8A—H8AA0.9800C8B—H8BA0.9800
C8A—H8AB0.9800C8B—H8BB0.9800
C8A—H8AC0.9800C8B—H8BC0.9800
O2A—S1A—O1A119.64 (5)O2B—S1B—O1B119.73 (5)
O2A—S1A—N1A110.25 (4)O2B—S1B—N1B110.14 (4)
O1A—S1A—N1A103.55 (4)O1B—S1B—N1B103.54 (4)
O2A—S1A—C6A108.95 (4)O2B—S1B—C6B109.19 (4)
O1A—S1A—C6A109.08 (4)O1B—S1B—C6B108.77 (4)
N1A—S1A—C6A104.24 (4)N1B—S1B—C6B104.31 (4)
C7A—N1A—S1A123.31 (6)C7B—N1B—S1B122.73 (6)
C7A—N1A—H1NA120.8 (9)C7B—N1B—H1NB120.4 (9)
S1A—N1A—H1NA114.7 (9)S1B—N1B—H1NB115.7 (9)
C2A—C1A—C6A119.21 (9)C2B—C1B—C6B119.35 (9)
C2A—C1A—H1AA120.4C2B—C1B—H1BA120.3
C6A—C1A—H1AA120.4C6B—C1B—H1BA120.3
C1A—C2A—C3A118.68 (9)C1B—C2B—C3B118.81 (9)
C1A—C2A—H2AA120.7C1B—C2B—H2BA120.6
C3A—C2A—H2AA120.7C3B—C2B—H2BA120.6
C4A—C3A—C2A122.38 (10)C4B—C3B—C2B122.34 (10)
C4A—C3A—Cl1A118.79 (8)C4B—C3B—Cl1B118.92 (8)
C2A—C3A—Cl1A118.81 (8)C2B—C3B—Cl1B118.73 (8)
C3A—C4A—C5A118.96 (9)C3B—C4B—C5B118.85 (9)
C3A—C4A—H4AA120.5C3B—C4B—H4BA120.6
C5A—C4A—H4AA120.5C5B—C4B—H4BA120.6
C4A—C5A—C6A118.98 (9)C4B—C5B—C6B119.03 (9)
C4A—C5A—H5AA120.5C4B—C5B—H5BA120.5
C6A—C5A—H5AA120.5C6B—C5B—H5BA120.5
C5A—C6A—C1A121.79 (9)C5B—C6B—C1B121.61 (9)
C5A—C6A—S1A119.51 (7)C5B—C6B—S1B120.13 (7)
C1A—C6A—S1A118.67 (7)C1B—C6B—S1B118.23 (7)
O3A—C7A—N1A121.09 (8)O3B—C7B—N1B120.88 (8)
O3A—C7A—C8A124.21 (8)O3B—C7B—C8B124.43 (8)
N1A—C7A—C8A114.69 (8)N1B—C7B—C8B114.68 (8)
C7A—C8A—H8AA109.5C7B—C8B—H8BA109.5
C7A—C8A—H8AB109.5C7B—C8B—H8BB109.5
H8AA—C8A—H8AB109.5H8BA—C8B—H8BB109.5
C7A—C8A—H8AC109.5C7B—C8B—H8BC109.5
H8AA—C8A—H8AC109.5H8BA—C8B—H8BC109.5
H8AB—C8A—H8AC109.5H8BB—C8B—H8BC109.5
O2A—S1A—N1A—C7A50.89 (9)O2B—S1B—N1B—C7B51.56 (9)
O1A—S1A—N1A—C7A179.98 (8)O1B—S1B—N1B—C7B179.27 (8)
C6A—S1A—N1A—C7A65.90 (8)C6B—S1B—N1B—C7B65.50 (8)
C6A—C1A—C2A—C3A0.07 (15)C6B—C1B—C2B—C3B0.04 (14)
C1A—C2A—C3A—C4A0.83 (16)C1B—C2B—C3B—C4B1.14 (16)
C1A—C2A—C3A—Cl1A177.29 (8)C1B—C2B—C3B—Cl1B177.27 (7)
C2A—C3A—C4A—C5A1.11 (16)C2B—C3B—C4B—C5B1.32 (16)
Cl1A—C3A—C4A—C5A177.02 (7)Cl1B—C3B—C4B—C5B177.08 (8)
C3A—C4A—C5A—C6A0.60 (15)C3B—C4B—C5B—C6B0.32 (15)
C4A—C5A—C6A—C1A0.14 (15)C4B—C5B—C6B—C1B0.83 (15)
C4A—C5A—C6A—S1A177.64 (7)C4B—C5B—C6B—S1B177.14 (7)
C2A—C1A—C6A—C5A0.41 (15)C2B—C1B—C6B—C5B1.02 (15)
C2A—C1A—C6A—S1A177.39 (8)C2B—C1B—C6B—S1B176.99 (7)
O2A—S1A—C6A—C5A18.56 (9)O2B—S1B—C6B—C5B21.27 (9)
O1A—S1A—C6A—C5A150.79 (8)O1B—S1B—C6B—C5B153.56 (8)
N1A—S1A—C6A—C5A99.12 (8)N1B—S1B—C6B—C5B96.44 (8)
O2A—S1A—C6A—C1A163.58 (8)O2B—S1B—C6B—C1B160.70 (8)
O1A—S1A—C6A—C1A31.36 (9)O1B—S1B—C6B—C1B28.41 (9)
N1A—S1A—C6A—C1A78.73 (8)N1B—S1B—C6B—C1B81.59 (8)
S1A—N1A—C7A—O3A3.57 (13)S1B—N1B—C7B—O3B1.87 (13)
S1A—N1A—C7A—C8A175.90 (7)S1B—N1B—C7B—C8B177.08 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1NB···O3Ai0.871 (15)1.939 (15)2.7980 (10)168.6 (13)
N1A—H1NA···O3Bii0.865 (15)1.939 (15)2.7952 (10)170.0 (13)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC8H8ClNO3S
Mr233.66
Crystal system, space groupMonoclinic, P2/c
Temperature (K)100
a, b, c (Å)12.1801 (6), 9.2529 (4), 17.6769 (8)
β (°) 101.979 (1)
V3)1948.83 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.36 × 0.14 × 0.14
Data collection
DiffractometerBruker APEX DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.819, 0.923
No. of measured, independent and
observed [I > 2σ(I)] reflections
45479, 7130, 5439
Rint0.033
(sin θ/λ)max1)0.759
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.090, 1.04
No. of reflections7130
No. of parameters263
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.48, 0.52

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1NB···O3Ai0.871 (15)1.939 (15)2.7980 (10)168.6 (13)
N1A—H1NA···O3Bii0.865 (15)1.939 (15)2.7952 (10)170.0 (13)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors are grateful to the Visvesvaraya Technological University, Jnana Sangama, Belgaum, for financial support through research project grant No. VTU/Aca./2010–11/A-9/11330 Dtd. 07–12–2010.

References

First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals
First citationFun, H.-K., Chia, T. S., Hegde, P., Jyothi, K. & D'Souza, P. R. (2012). Acta Cryst. E68, o2025.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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