N-(2-Chloro­phen­yl)benzene­sulfonamide

In the crystal structure of the title compound, C₁₂H₁₀ClNO₂S, mol­ecules form chains via hydrogen bonds, which create infinite helices along the c axis. The hydrogen-bond network can be described by graph set C(4) (an infinite chain with four atoms in the repeat pattern).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.100
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       5.33 su
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C5     -   H5     ...       0.83 Ang.
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N1     -   H1     ...       0.74 Ang.

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

   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CELDIM in CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW in SHELXL97; software used to prepare material for publication: CIFTAB in SHELXL97.

N-(2-Chlorophenyl)benzenesulfonamide

Crystal data

C12H10ClNO2S	F(000) = 552
Mr = 267.72	Dx = 1.487 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 14.821 (3) Å	Cell parameters from 26 reflections
b = 9.656 (2) Å	θ = 5–10°
c = 8.365 (2) Å	µ = 0.48 mm^−1
β = 92.46 (3)°	T = 293 K
V = 1196.0 (4) Å^3	Prism, colourless
Z = 4	0.4 × 0.3 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.027
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.4°
Graphite monochromator	h = −17→17
ω–2θ scans	k = 0→11
2262 measured reflections	l = 0→9
2108 independent reflections	3 standard reflections every 120 min
1727 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0669P)^2 + 0.0406P] where P = (Fo^2 + 2Fc^2)/3
2108 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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
S	0.78658 (3)	0.06254 (4)	0.40936 (5)	0.03269 (17)
Cl	0.59519 (4)	−0.20847 (6)	0.23017 (8)	0.0639 (2)
O1	0.85365 (9)	−0.00117 (15)	0.51171 (15)	0.0446 (3)
O2	0.77374 (9)	0.20887 (13)	0.41317 (16)	0.0445 (3)
N1	0.69062 (10)	−0.00742 (17)	0.45428 (18)	0.0357 (4)
C1	0.80792 (12)	0.01758 (19)	0.2098 (2)	0.0337 (4)
C2	0.87507 (16)	−0.0759 (2)	0.1800 (2)	0.0477 (5)
C3	0.8922 (2)	−0.1097 (3)	0.0239 (3)	0.0621 (6)
C4	0.84126 (19)	−0.0531 (3)	−0.1008 (3)	0.0584 (6)
C5	0.77488 (17)	0.0398 (3)	−0.0706 (3)	0.0558 (6)
C6	0.75731 (15)	0.0777 (2)	0.0849 (2)	0.0452 (5)
C7	0.60828 (12)	0.03916 (18)	0.3793 (2)	0.0341 (4)
C8	0.55762 (13)	−0.0441 (2)	0.2742 (2)	0.0402 (4)
C9	0.47735 (15)	0.0028 (3)	0.2046 (3)	0.0519 (5)
C10	0.44732 (15)	0.1329 (3)	0.2367 (3)	0.0581 (6)
C11	0.49725 (16)	0.2170 (3)	0.3394 (3)	0.0563 (6)
C12	0.57632 (14)	0.1699 (2)	0.4119 (3)	0.0455 (5)
H1	0.6943 (14)	−0.082 (2)	0.476 (2)	0.030 (5)*
H2	0.9127 (19)	−0.106 (3)	0.275 (3)	0.070 (8)*
H3	0.9419 (19)	−0.167 (3)	0.008 (3)	0.073 (8)*
H4	0.8514 (18)	−0.079 (3)	−0.200 (3)	0.065 (7)*
H5	0.747 (2)	0.077 (3)	−0.148 (3)	0.072 (8)*
H6	0.7160 (15)	0.140 (2)	0.103 (3)	0.041 (6)*
H9	0.446 (2)	−0.057 (3)	0.138 (3)	0.081 (9)*
H10	0.3944 (19)	0.158 (3)	0.199 (3)	0.068 (8)*
H11	0.4815 (18)	0.300 (3)	0.363 (3)	0.063 (7)*
H12	0.6093 (16)	0.224 (2)	0.490 (3)	0.051 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0357 (3)	0.0326 (3)	0.0296 (3)	−0.00266 (16)	−0.00082 (17)	−0.00145 (16)
Cl	0.0652 (4)	0.0470 (3)	0.0780 (4)	0.0054 (2)	−0.0154 (3)	−0.0219 (3)
O1	0.0446 (7)	0.0554 (9)	0.0331 (7)	0.0026 (6)	−0.0063 (5)	0.0004 (6)
O2	0.0475 (8)	0.0323 (7)	0.0539 (8)	−0.0067 (6)	0.0039 (6)	−0.0066 (6)
N1	0.0418 (9)	0.0297 (8)	0.0356 (8)	−0.0003 (7)	0.0032 (6)	0.0050 (7)
C1	0.0380 (10)	0.0345 (9)	0.0284 (9)	−0.0067 (7)	0.0005 (7)	0.0025 (7)
C2	0.0587 (13)	0.0482 (11)	0.0365 (10)	0.0123 (9)	0.0052 (9)	0.0026 (8)
C3	0.0822 (18)	0.0615 (15)	0.0438 (12)	0.0172 (13)	0.0156 (11)	−0.0021 (10)
C4	0.0786 (17)	0.0638 (15)	0.0336 (11)	−0.0059 (12)	0.0123 (11)	−0.0009 (10)
C5	0.0634 (14)	0.0710 (16)	0.0323 (11)	−0.0109 (11)	−0.0072 (10)	0.0157 (10)
C6	0.0444 (12)	0.0520 (12)	0.0391 (10)	0.0019 (9)	0.0002 (8)	0.0104 (9)
C7	0.0350 (9)	0.0347 (9)	0.0333 (9)	−0.0012 (7)	0.0082 (7)	0.0034 (7)
C8	0.0408 (10)	0.0415 (10)	0.0387 (10)	0.0003 (8)	0.0049 (8)	−0.0009 (8)
C9	0.0419 (11)	0.0647 (14)	0.0487 (12)	0.0014 (10)	−0.0038 (9)	−0.0011 (10)
C10	0.0411 (12)	0.0742 (16)	0.0591 (14)	0.0148 (11)	0.0047 (10)	0.0140 (12)
C11	0.0495 (12)	0.0466 (12)	0.0742 (15)	0.0151 (10)	0.0191 (11)	0.0069 (11)
C12	0.0435 (11)	0.0415 (11)	0.0525 (12)	0.0000 (9)	0.0128 (9)	−0.0050 (9)

Geometric parameters (Å, º)

S—O1	1.4236 (14)	C4—H4	0.89 (3)
S—O2	1.4262 (14)	C5—C6	1.387 (3)
S—N1	1.6328 (16)	C5—H5	0.83 (3)
S—C1	1.7666 (18)	C6—H6	0.88 (2)
Cl—C8	1.727 (2)	C7—C12	1.380 (3)
N1—C7	1.421 (2)	C7—C8	1.388 (3)
N1—H1	0.75 (2)	C8—C9	1.378 (3)
C1—C2	1.374 (3)	C9—C10	1.364 (3)
C1—C6	1.387 (3)	C9—H9	0.92 (3)
C2—C3	1.380 (3)	C10—C11	1.375 (4)
C2—H2	1.00 (3)	C10—H10	0.87 (3)
C3—C4	1.374 (4)	C11—C12	1.374 (3)
C3—H3	0.94 (3)	C11—H11	0.86 (3)
C4—C5	1.363 (4)	C12—H12	0.96 (2)
O1—S—O2	120.34 (8)	C6—C5—H5	121 (2)
O1—S—N1	105.98 (9)	C5—C6—C1	118.6 (2)
O2—S—N1	106.65 (8)	C5—C6—H6	120.1 (14)
O1—S—C1	108.26 (9)	C1—C6—H6	121.2 (14)
O2—S—C1	107.10 (8)	C12—C7—C8	118.29 (18)
N1—S—C1	107.99 (8)	C12—C7—N1	119.88 (17)
C7—N1—S	120.50 (13)	C8—C7—N1	121.82 (17)
C7—N1—H1	117.8 (16)	C9—C8—C7	120.74 (19)
S—N1—H1	113.7 (16)	C9—C8—Cl	119.47 (17)
C2—C1—C6	120.73 (18)	C7—C8—Cl	119.79 (15)
C2—C1—S	119.54 (14)	C10—C9—C8	120.2 (2)
C6—C1—S	119.73 (15)	C10—C9—H9	122 (2)
C1—C2—C3	119.4 (2)	C8—C9—H9	117.4 (19)
C1—C2—H2	115.6 (16)	C9—C10—C11	119.7 (2)
C3—C2—H2	124.6 (16)	C9—C10—H10	118.8 (19)
C4—C3—C2	120.5 (2)	C11—C10—H10	121.2 (19)
C4—C3—H3	122.4 (17)	C12—C11—C10	120.4 (2)
C2—C3—H3	117.0 (17)	C12—C11—H11	116.3 (17)
C5—C4—C3	119.9 (2)	C10—C11—H11	123.2 (17)
C5—C4—H4	120.7 (18)	C11—C12—C7	120.6 (2)
C3—C4—H4	119.4 (18)	C11—C12—H12	121.5 (14)
C4—C5—C6	120.9 (2)	C7—C12—H12	117.8 (14)
C4—C5—H5	118 (2)
O1—S—N1—C7	176.44 (13)	C2—C1—C6—C5	1.1 (3)
O2—S—N1—C7	47.10 (15)	S—C1—C6—C5	−179.47 (16)
C1—S—N1—C7	−67.72 (15)	S—N1—C7—C12	−68.3 (2)
O1—S—C1—C2	5.83 (19)	S—N1—C7—C8	112.41 (17)
O2—S—C1—C2	136.98 (16)	C12—C7—C8—C9	−0.2 (3)
N1—S—C1—C2	−108.50 (17)	N1—C7—C8—C9	179.15 (18)
O1—S—C1—C6	−173.63 (15)	C12—C7—C8—Cl	180.00 (14)
O2—S—C1—C6	−42.48 (17)	N1—C7—C8—Cl	−0.7 (2)
N1—S—C1—C6	72.04 (17)	C7—C8—C9—C10	0.9 (3)
C6—C1—C2—C3	0.1 (3)	Cl—C8—C9—C10	−179.22 (17)
S—C1—C2—C3	−179.32 (19)	C8—C9—C10—C11	−0.3 (3)
C1—C2—C3—C4	−1.6 (4)	C9—C10—C11—C12	−1.1 (3)
C2—C3—C4—C5	1.7 (4)	C10—C11—C12—C7	1.9 (3)
C3—C4—C5—C6	−0.5 (4)	C8—C7—C12—C11	−1.3 (3)
C4—C5—C6—C1	−0.9 (3)	N1—C7—C12—C11	179.42 (18)