The crystal structure of the title compound, C12H10ClNO2S, has been determined. The molecules of the substance form chains with adjacent molecules by means of hydrogen bonds, which create infinite helicoids along the b axis. The hydrogen-bond network can be described by the graph-set as C(4) (infinite chain with four atoms in the repeat pattern).
Supporting information
CCDC reference: 296651
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.127
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.47 Deg.
| Author Response: ...At collecting procedure of the data it was chosen the angle
providing 10 reflections per one improved parameter
(H- atoms have been excluded for exception of H-atom at the N-atom).
|
Alert level B
THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5604
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.47 Deg.
Alert level C
ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
Absorption corrections should be applied.
Tmin and Tmax expected: 0.805 0.955
RT(exp) = 1.186
PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.19
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
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... O2A
H1 O2A
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... O2A
N1 O2A
PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... O2A
N1 H1 O2A
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 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
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
The chemical synthesis of the title compound has been performed in analogy to procedures described previously (Crosley et al., 1940; Anderson et al., 1942; Gutsche et al., 1974) by reaction of a substituted aromatic amine (here chloroaniline) with benzenesulfonyl chloride in dry pyridine, followed by precipitation of the end product by pouring the reaction mixture into water and by acidification to pH 5. Generally the compounds have been recrystallized from ethanol/water. The N-(4-chlorophenyl)benzenesulfonamide single crystals were grown from water–ethanol solution by saturation through vapor phase.
Data collection: CAD-4-PC Software (Enraf–Nonius, 1989); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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-(4-Chlorophenyl)benzenesulfonamide
top
Crystal data top
C12H10ClNO2S | Dx = 1.428 Mg m−3 |
Mr = 267.72 | Mo Kα radiation, λ = 0.71070 Å |
Orthorhombic, Pbca | Cell parameters from 35 reflections |
a = 10.840 (2) Å | θ = 5–12° |
b = 9.740 (1) Å | µ = 0.46 mm−1 |
c = 23.596 (3) Å | T = 293 K |
V = 2491.3 (6) Å3 | Prism, colourless |
Z = 8 | 0.5 × 0.4 × 0.1 mm |
F(000) = 1104 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 23.5°, θmin = 1.7° |
Graphite monochromator | h = 0→12 |
ω–2θ scans | k = 0→10 |
1838 measured reflections | l = −26→0 |
1838 independent reflections | 3 standard reflections every 120 min |
1568 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.075P)2 + 2.965P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
1838 reflections | Δρmax = 0.41 e Å−3 |
158 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0094 (9) |
Crystal data top
C12H10ClNO2S | V = 2491.3 (6) Å3 |
Mr = 267.72 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.840 (2) Å | µ = 0.46 mm−1 |
b = 9.740 (1) Å | T = 293 K |
c = 23.596 (3) Å | 0.5 × 0.4 × 0.1 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
1838 measured reflections | θmax = 23.5° |
1838 independent reflections | 3 standard reflections every 120 min |
1568 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.41 e Å−3 |
1838 reflections | Δρmin = −0.34 e Å−3 |
158 parameters | |
Special details top
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 | x | y | z | Uiso*/Ueq | |
S | 0.22728 (7) | 0.21069 (8) | 0.38748 (4) | 0.0437 (3) | |
Cl | −0.37869 (8) | 0.04409 (11) | 0.44136 (5) | 0.0684 (4) | |
O1 | 0.3562 (2) | 0.1825 (3) | 0.38751 (11) | 0.0600 (7) | |
O2 | 0.1843 (2) | 0.3418 (2) | 0.40588 (11) | 0.0582 (7) | |
N1 | 0.1653 (3) | 0.0940 (3) | 0.42721 (12) | 0.0433 (7) | |
H1 | 0.201 (3) | 0.024 (4) | 0.4223 (16) | 0.052* | |
C1 | 0.1696 (3) | 0.1876 (4) | 0.31852 (15) | 0.0496 (9) | |
C2 | 0.2243 (4) | 0.0920 (5) | 0.28367 (18) | 0.0738 (12) | |
H2 | 0.2903 | 0.0394 | 0.2964 | 0.089* | |
C3 | 0.1784 (5) | 0.0753 (7) | 0.2286 (2) | 0.1036 (18) | |
H3 | 0.2141 | 0.0107 | 0.2046 | 0.124* | |
C4 | 0.0822 (6) | 0.1528 (7) | 0.2098 (2) | 0.1030 (18) | |
H4 | 0.0536 | 0.1435 | 0.1728 | 0.124* | |
C5 | 0.0279 (5) | 0.2450 (6) | 0.2461 (2) | 0.0983 (17) | |
H5 | −0.0401 | 0.2952 | 0.2340 | 0.118* | |
C6 | 0.0716 (4) | 0.2638 (5) | 0.29876 (18) | 0.0710 (12) | |
H6 | 0.0353 | 0.3291 | 0.3222 | 0.085* | |
C7 | 0.0330 (3) | 0.0819 (3) | 0.43086 (12) | 0.0384 (7) | |
C8 | −0.0256 (3) | −0.0288 (3) | 0.40637 (14) | 0.0458 (8) | |
H8 | 0.0204 | −0.0952 | 0.3875 | 0.055* | |
C9 | −0.1523 (3) | −0.0415 (3) | 0.40982 (15) | 0.0487 (9) | |
H9 | −0.1923 | −0.1164 | 0.3937 | 0.058* | |
C10 | −0.2183 (3) | 0.0586 (3) | 0.43754 (14) | 0.0448 (8) | |
C11 | −0.1614 (3) | 0.1686 (3) | 0.46195 (14) | 0.0483 (8) | |
H11 | −0.2076 | 0.2352 | 0.4805 | 0.058* | |
C12 | −0.0346 (3) | 0.1803 (3) | 0.45892 (14) | 0.0459 (8) | |
H12 | 0.0050 | 0.2544 | 0.4758 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0384 (5) | 0.0411 (5) | 0.0515 (5) | −0.0064 (3) | −0.0042 (4) | −0.0013 (4) |
Cl | 0.0405 (5) | 0.0753 (7) | 0.0893 (8) | 0.0013 (4) | 0.0105 (5) | 0.0012 (5) |
O1 | 0.0347 (12) | 0.0656 (16) | 0.0795 (17) | −0.0081 (11) | −0.0067 (12) | −0.0020 (14) |
O2 | 0.0591 (15) | 0.0365 (13) | 0.0790 (17) | −0.0069 (11) | −0.0015 (13) | −0.0081 (12) |
N1 | 0.0391 (15) | 0.0406 (16) | 0.0502 (16) | 0.0050 (12) | −0.0043 (12) | 0.0020 (13) |
C1 | 0.0432 (19) | 0.050 (2) | 0.055 (2) | −0.0118 (16) | −0.0021 (16) | 0.0038 (16) |
C2 | 0.071 (3) | 0.088 (3) | 0.062 (2) | 0.003 (2) | −0.005 (2) | −0.019 (2) |
C3 | 0.104 (4) | 0.135 (5) | 0.071 (3) | −0.010 (4) | 0.010 (3) | −0.037 (3) |
C4 | 0.102 (4) | 0.144 (5) | 0.063 (3) | −0.022 (4) | −0.024 (3) | 0.000 (3) |
C5 | 0.092 (4) | 0.114 (4) | 0.089 (3) | 0.000 (3) | −0.041 (3) | 0.021 (3) |
C6 | 0.063 (3) | 0.074 (3) | 0.076 (3) | 0.004 (2) | −0.018 (2) | 0.008 (2) |
C7 | 0.0405 (17) | 0.0354 (16) | 0.0394 (16) | 0.0021 (14) | −0.0026 (14) | 0.0072 (13) |
C8 | 0.0449 (19) | 0.0392 (18) | 0.0532 (19) | 0.0044 (15) | 0.0044 (16) | −0.0056 (15) |
C9 | 0.0461 (19) | 0.0417 (19) | 0.058 (2) | −0.0047 (15) | 0.0020 (17) | −0.0049 (16) |
C10 | 0.0404 (19) | 0.0497 (19) | 0.0444 (17) | 0.0026 (15) | 0.0044 (14) | 0.0089 (15) |
C11 | 0.050 (2) | 0.045 (2) | 0.0492 (18) | 0.0087 (16) | 0.0091 (16) | 0.0017 (16) |
C12 | 0.0505 (19) | 0.0394 (18) | 0.0477 (18) | 0.0012 (16) | 0.0000 (16) | −0.0003 (14) |
Geometric parameters (Å, º) top
S—O1 | 1.425 (3) | C4—H4 | 0.9300 |
S—O2 | 1.427 (2) | C5—C6 | 1.343 (6) |
S—N1 | 1.619 (3) | C5—H5 | 0.9300 |
S—C1 | 1.758 (4) | C6—H6 | 0.9300 |
Cl—C10 | 1.747 (3) | C7—C12 | 1.375 (4) |
N1—C7 | 1.442 (4) | C7—C8 | 1.378 (4) |
N1—H1 | 0.80 (4) | C8—C9 | 1.382 (5) |
C1—C6 | 1.377 (5) | C8—H8 | 0.9300 |
C1—C2 | 1.377 (5) | C9—C10 | 1.375 (5) |
C2—C3 | 1.402 (7) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—C11 | 1.364 (5) |
C3—C4 | 1.362 (8) | C11—C12 | 1.381 (5) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.374 (8) | C12—H12 | 0.9300 |
| | | |
O1—S—O2 | 119.49 (15) | C4—C5—H5 | 119.5 |
O1—S—N1 | 105.76 (15) | C5—C6—C1 | 120.8 (5) |
O2—S—N1 | 108.46 (16) | C5—C6—H6 | 119.6 |
O1—S—C1 | 108.95 (17) | C1—C6—H6 | 119.6 |
O2—S—C1 | 106.26 (17) | C12—C7—C8 | 120.1 (3) |
N1—S—C1 | 107.39 (15) | C12—C7—N1 | 120.1 (3) |
C7—N1—S | 120.3 (2) | C8—C7—N1 | 119.8 (3) |
C7—N1—H1 | 115 (3) | C7—C8—C9 | 120.2 (3) |
S—N1—H1 | 108 (3) | C7—C8—H8 | 119.9 |
C6—C1—C2 | 119.6 (4) | C9—C8—H8 | 119.9 |
C6—C1—S | 121.3 (3) | C10—C9—C8 | 118.8 (3) |
C2—C1—S | 119.1 (3) | C10—C9—H9 | 120.6 |
C1—C2—C3 | 118.7 (5) | C8—C9—H9 | 120.6 |
C1—C2—H2 | 120.7 | C11—C10—C9 | 121.5 (3) |
C3—C2—H2 | 120.7 | C11—C10—Cl | 119.5 (3) |
C4—C3—C2 | 120.6 (5) | C9—C10—Cl | 119.0 (3) |
C4—C3—H3 | 119.7 | C10—C11—C12 | 119.6 (3) |
C2—C3—H3 | 119.7 | C10—C11—H11 | 120.2 |
C3—C4—C5 | 119.2 (5) | C12—C11—H11 | 120.2 |
C3—C4—H4 | 120.4 | C7—C12—C11 | 119.8 (3) |
C5—C4—H4 | 120.4 | C7—C12—H12 | 120.1 |
C6—C5—C4 | 121.0 (5) | C11—C12—H12 | 120.1 |
C6—C5—H5 | 119.5 | | |
| | | |
O1—S—N1—C7 | −172.3 (2) | C2—C1—C6—C5 | 0.7 (7) |
O2—S—N1—C7 | 58.4 (3) | S—C1—C6—C5 | −179.7 (4) |
C1—S—N1—C7 | −56.1 (3) | S—N1—C7—C12 | −71.1 (4) |
O1—S—C1—C6 | −148.9 (3) | S—N1—C7—C8 | 109.2 (3) |
O2—S—C1—C6 | −18.9 (4) | C12—C7—C8—C9 | 0.1 (5) |
N1—S—C1—C6 | 97.0 (3) | N1—C7—C8—C9 | 179.8 (3) |
O1—S—C1—C2 | 30.7 (4) | C7—C8—C9—C10 | 0.6 (5) |
O2—S—C1—C2 | 160.7 (3) | C8—C9—C10—C11 | −0.6 (5) |
N1—S—C1—C2 | −83.4 (3) | C8—C9—C10—Cl | 179.3 (3) |
C6—C1—C2—C3 | 0.3 (7) | C9—C10—C11—C12 | 0.0 (5) |
S—C1—C2—C3 | −179.4 (4) | Cl—C10—C11—C12 | −179.9 (3) |
C1—C2—C3—C4 | 0.4 (8) | C8—C7—C12—C11 | −0.7 (5) |
C2—C3—C4—C5 | −1.9 (9) | N1—C7—C12—C11 | 179.6 (3) |
C3—C4—C5—C6 | 2.9 (9) | C10—C11—C12—C7 | 0.7 (5) |
C4—C5—C6—C1 | −2.3 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2Ai | 0.78 (3) | 2.21 (3) | 2.993 (4) | 175 (4) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Experimental details
Crystal data |
Chemical formula | C12H10ClNO2S |
Mr | 267.72 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 10.840 (2), 9.740 (1), 23.596 (3) |
V (Å3) | 2491.3 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.46 |
Crystal size (mm) | 0.5 × 0.4 × 0.1 |
|
Data collection |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1838, 1838, 1568 |
Rint | 0.000 |
θmax (°) | 23.5 |
(sin θ/λ)max (Å−1) | 0.560 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.127, 1.15 |
No. of reflections | 1838 |
No. of parameters | 158 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.34 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2Ai | 0.78 (3) | 2.212 (34) | 2.993 (4) | 175 (4) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Sulfanyls and sulfonamides are drugs used for the treatment of infections, some fungi and certain protozoa. Other therapeutic applications of the compounds are as diuretic and hypoglycaemic agents. On the other hand, the compounds are very interesting from a fundamental point of view, for studying the relationship between van der Waals interactions and hydrogen-bond topology forming a crystal lattice architecture.
A view of the N-(4-chlorophenyl)benzenesulfonamide molecule, (I), with the atomic numbering is presented in Fig. 1. The conformational state of the molecule in the crystal structure can be characterized in the following way. The torsion angle O1—S—C1—C2, which characterizes the arrangement between the SO2 group and the phenyl motif Ph1 (C1–C6), is 30.7 (4) Å. The phenyl fragments are rotated relative to each other by 54.39 (15)°. The torsion angle N1—S—C1—C2, which describes the position of the NH group relative to the Ph1 fragment, is −83.4 (3)°, whereas the torsion angle S—N1—C7—C12, which characterizes the location of the SO2 group with respect to the Ph2 (C7–C12) ring, is −71.1 (4)°.
One molecule of the outlined crystal structure has two equivalent hydrogen bonds: N1—H1···O2i and O2···(H1—N1)i. The values of the hydrogen-bond geometric parameters are summarized in Table 1.
The molecular packing architecture is shown in Fig. 2. The molecules of (I) form chains with adjacent molecules by means of the hydrogen bonds described above. The hydrogen bonds create infinite helicoids along the OY axis. The hydrogen-bond network can be described by the graph-set assignment introduced by Etter (1990) as C4 (infinite chain with four involved atoms). The chains form a complex layer structure which can be characterized as follows. The layer includes two types of chains which are situated in such a way that the periphery consists of the chlorophenyl motifs whereas the inside part consists of the unsubstituted phenyl rings. The chlorophenyl fragments of adjacent layers are approximately parallel and interact with each other only by van der Waals forces. The unsubstituted phenyl rings also interact with each other by van der Waals forces, but because of the non-coplanar arrangement the energy of these interactions is lower than the analogous one for the chlorophenyl fragments. These conclusions are confirmed by our data received from sublimation experiments and will be published in the near future.