N-(2,3-Dichloro­phen­yl)benzene­sulfonamide

In the crystal structure of the title compound, C₁₂H₉Cl₂NO₂S, the dihedral angle between the two benzene rings is 54.8 (2)°. Inter­molecular N—H...O hydrogen bonds lead to infinite helices along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.049
• wR factor = 0.103
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.87

Author Response: Due to not so good quality of the single crystal. For this compound it is very difficult to prepare the single crystals.

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full          25.00
           From the CIF: _reflns_number_total               2022
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2319
           Completeness (_total/calc)             87.19%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.87

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N1     -   H1     ...       0.76 Ang.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 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
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1989); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

N-(2,3-Dichlorophenyl)benzenesulfonamide

Crystal data

C12H9Cl2NO2S	Dx = 1.524 Mg m^−3
Mr = 302.16	Melting point: 387.2 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.466 (1) Å	Cell parameters from 35 reflections
b = 9.805 (1) Å	θ = 5–12°
c = 15.876 (2) Å	µ = 0.64 mm^−1
β = 92.10 (1)°	T = 293 K
V = 1317.0 (3) Å^3	Prism, colourless
Z = 4	0.28 × 0.2 × 0.11 mm
F(000) = 616

Data collection

Bruker P4 diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.4°
Graphite monochromator	h = −10→1
ω–2θ scans	k = −11→1
2824 measured reflections	l = −18→18
2022 independent reflections	3 standard reflections every 120 min
1152 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.034P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
2022 reflections	Δρmax = 0.24 e Å^−3
167 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (9)

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
S1	0.91244 (13)	0.08296 (11)	0.71431 (7)	0.0469 (3)
Cl1	0.75548 (16)	−0.18271 (12)	0.89767 (8)	0.0736 (5)
Cl2	0.64362 (16)	−0.07756 (15)	1.07167 (8)	0.0865 (5)
O1	1.0071 (3)	0.0155 (3)	0.65482 (17)	0.0593 (9)
O2	0.9226 (4)	0.2272 (3)	0.72520 (17)	0.0602 (9)
N1	0.9593 (5)	0.0148 (3)	0.8059 (2)	0.0490 (10)
H1	0.974 (5)	−0.061 (4)	0.801 (2)	0.054*
C1	0.7129 (5)	0.0437 (4)	0.6901 (2)	0.0440 (11)
C2	0.6772 (6)	−0.0515 (5)	0.6292 (3)	0.0705 (14)
H2	0.7573	−0.0955	0.6013	0.085*
C3	0.5197 (7)	−0.0815 (5)	0.6097 (4)	0.0964 (19)
H3	0.4938	−0.1437	0.5672	0.116*
C4	0.4032 (7)	−0.0197 (7)	0.6528 (4)	0.096 (2)
H4	0.2981	−0.0428	0.6411	0.116*
C5	0.4392 (7)	0.0756 (7)	0.7127 (3)	0.0825 (18)
H5	0.3586	0.1188	0.7407	0.099*
C6	0.5953 (6)	0.1086 (5)	0.7323 (3)	0.0666 (14)
H6	0.6202	0.1737	0.7733	0.080*
C7	0.8956 (5)	0.0629 (4)	0.8824 (2)	0.0401 (10)
C8	0.8043 (5)	−0.0214 (4)	0.9315 (3)	0.0458 (11)
C9	0.7513 (5)	0.0268 (5)	1.0073 (3)	0.0553 (13)
C10	0.7851 (6)	0.1582 (6)	1.0338 (3)	0.0667 (14)
H10	0.7487	0.1898	1.0848	0.080*
C11	0.8722 (6)	0.2411 (5)	0.9847 (3)	0.0665 (14)
H11	0.8935	0.3302	1.0016	0.080*
C12	0.9294 (5)	0.1931 (4)	0.9094 (3)	0.0535 (12)
H12	0.9911	0.2496	0.8769	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0495 (7)	0.0397 (6)	0.0519 (7)	−0.0021 (6)	0.0057 (6)	0.0044 (6)
Cl1	0.0902 (10)	0.0505 (7)	0.0807 (9)	−0.0211 (7)	0.0110 (8)	−0.0053 (7)
Cl2	0.0807 (10)	0.1118 (12)	0.0680 (8)	−0.0080 (10)	0.0158 (7)	0.0204 (9)
O1	0.0559 (19)	0.066 (2)	0.0576 (18)	0.0005 (17)	0.0228 (17)	−0.0032 (16)
O2	0.082 (2)	0.0384 (17)	0.0604 (19)	−0.0101 (17)	0.0032 (17)	0.0082 (14)
N1	0.053 (2)	0.037 (2)	0.056 (2)	0.006 (2)	−0.005 (2)	0.001 (2)
C1	0.045 (3)	0.044 (3)	0.043 (3)	0.007 (2)	0.002 (2)	0.011 (2)
C2	0.052 (3)	0.060 (3)	0.099 (4)	0.007 (3)	−0.007 (3)	−0.014 (3)
C3	0.067 (4)	0.071 (4)	0.149 (5)	0.001 (4)	−0.033 (4)	−0.018 (4)
C4	0.047 (4)	0.109 (5)	0.133 (6)	−0.001 (4)	−0.003 (4)	0.036 (5)
C5	0.057 (4)	0.124 (5)	0.067 (4)	0.035 (4)	0.013 (3)	0.024 (4)
C6	0.061 (3)	0.090 (4)	0.049 (3)	0.022 (3)	0.006 (3)	0.007 (3)
C7	0.045 (2)	0.032 (2)	0.043 (2)	0.003 (2)	−0.007 (2)	0.000 (2)
C8	0.047 (3)	0.043 (2)	0.047 (3)	−0.002 (2)	−0.009 (2)	0.001 (2)
C9	0.056 (3)	0.063 (3)	0.047 (3)	0.000 (3)	−0.004 (3)	0.006 (2)
C10	0.076 (4)	0.077 (4)	0.046 (3)	0.013 (3)	−0.010 (3)	−0.016 (3)
C11	0.092 (4)	0.046 (3)	0.060 (3)	0.003 (3)	−0.009 (3)	−0.009 (3)
C12	0.057 (3)	0.044 (3)	0.059 (3)	−0.004 (2)	−0.010 (3)	0.005 (2)

Geometric parameters (Å, º)

S1—O1	1.424 (3)	C4—C5	1.360 (7)
S1—O2	1.427 (3)	C4—H4	0.9300
S1—N1	1.636 (4)	C5—C6	1.384 (6)
S1—C1	1.761 (4)	C5—H5	0.9300
Cl1—C8	1.716 (4)	C6—H6	0.9300
Cl2—C9	1.729 (5)	C7—C12	1.373 (5)
N1—C7	1.427 (5)	C7—C8	1.390 (5)
N1—H1	0.76 (4)	C8—C9	1.383 (5)
C1—C2	1.369 (5)	C9—C10	1.382 (6)
C1—C6	1.377 (6)	C10—C11	1.362 (6)
C2—C3	1.389 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.388 (6)
C3—C4	1.363 (7)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
O1—S1—O2	120.53 (19)	C6—C5—H5	119.8
O1—S1—N1	106.02 (19)	C1—C6—C5	119.0 (5)
O2—S1—N1	106.58 (18)	C1—C6—H6	120.5
O1—S1—C1	108.19 (19)	C5—C6—H6	120.5
O2—S1—C1	107.2 (2)	C12—C7—C8	119.5 (4)
N1—S1—C1	107.70 (19)	C12—C7—N1	119.4 (4)
C7—N1—S1	122.4 (3)	C8—C7—N1	121.1 (4)
C7—N1—H1	119 (3)	C9—C8—C7	119.3 (4)
S1—N1—H1	110 (3)	C9—C8—Cl1	120.4 (4)
C2—C1—C6	120.9 (4)	C7—C8—Cl1	120.3 (3)
C2—C1—S1	119.2 (3)	C10—C9—C8	120.9 (4)
C6—C1—S1	119.9 (4)	C10—C9—Cl2	118.7 (4)
C1—C2—C3	119.2 (5)	C8—C9—Cl2	120.5 (4)
C1—C2—H2	120.4	C11—C10—C9	119.5 (4)
C3—C2—H2	120.4	C11—C10—H10	120.3
C4—C3—C2	120.0 (5)	C9—C10—H10	120.3
C4—C3—H3	120.0	C10—C11—C12	120.3 (4)
C2—C3—H3	120.0	C10—C11—H11	119.9
C5—C4—C3	120.6 (6)	C12—C11—H11	119.9
C5—C4—H4	119.7	C7—C12—C11	120.5 (4)
C3—C4—H4	119.7	C7—C12—H12	119.7
C4—C5—C6	120.4 (5)	C11—C12—H12	119.7
C4—C5—H5	119.8
O1—S1—N1—C7	175.8 (3)	S1—N1—C7—C12	−63.8 (5)
O2—S1—N1—C7	46.2 (4)	S1—N1—C7—C8	118.4 (4)
C1—S1—N1—C7	−68.6 (4)	C12—C7—C8—C9	−1.0 (6)
O1—S1—C1—C2	7.4 (4)	N1—C7—C8—C9	176.8 (4)
O2—S1—C1—C2	138.8 (3)	C12—C7—C8—Cl1	178.0 (3)
N1—S1—C1—C2	−106.8 (3)	N1—C7—C8—Cl1	−4.2 (5)
O1—S1—C1—C6	−172.6 (3)	C7—C8—C9—C10	1.3 (6)
O2—S1—C1—C6	−41.2 (4)	Cl1—C8—C9—C10	−177.7 (3)
N1—S1—C1—C6	73.2 (4)	C7—C8—C9—Cl2	−177.6 (3)
C6—C1—C2—C3	0.5 (7)	Cl1—C8—C9—Cl2	3.4 (5)
S1—C1—C2—C3	−179.4 (4)	C8—C9—C10—C11	−0.2 (7)
C1—C2—C3—C4	−2.1 (8)	Cl2—C9—C10—C11	178.8 (4)
C2—C3—C4—C5	2.7 (9)	C9—C10—C11—C12	−1.3 (7)
C3—C4—C5—C6	−1.6 (9)	C8—C7—C12—C11	−0.5 (6)
C2—C1—C6—C5	0.5 (6)	N1—C7—C12—C11	−178.3 (4)
S1—C1—C6—C5	−179.5 (3)	C10—C11—C12—C7	1.7 (7)
C4—C5—C6—C1	0.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.76 (4)	2.30 (4)	3.039 (4)	166 (4)

Symmetry code: (i) −x+2, y−1/2, −z+3/2.