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In the crystal structure of the title compound, C12H10Cl2N2O2S, there are two independent mol­ecules in the asymmetric unit. Hydrogen bonds between NH2 and SO2 groups link molecules into layers, which inter­act with each other only by van der Waals forces

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047398/sg2084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047398/sg2084Isup2.hkl
Contains datablock I

CCDC reference: 630456

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.029
  • wR factor = 0.080
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O2 .. 3.02 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H22A .. O21 .. 2.94 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C12 H10 Cl2 N2 O2 S
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (reference?); software used to prepare material for publication: CIFTAB (reference?).

4-Amino-N-(2,3-dichlorophenyl)benzenesulfonamide top
Crystal data top
C12H10Cl2N2O2SF(000) = 648
Mr = 317.18Dx = 1.568 Mg m3
Triclinic, P1Melting point: 454.3(2) K
a = 7.4700 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.613 (1) ÅCell parameters from 35 reflections
c = 14.548 (1) Åθ = 5–12°
α = 110.91 (1)°µ = 0.64 mm1
β = 90.51 (1)°T = 200 K
γ = 102.42 (1)°Prism, colourless
V = 1343.6 (2) Å30.4 × 0.2 × 0.2 mm
Z = 4
Data collection top
Siemens P4
diffractometer
Rint = 0.011
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.8°
Graphite monochromatorh = 18
ω–2θ scansk = 1514
5502 measured reflectionsl = 1717
4499 independent reflections3 standard reflections every 2 reflections
4325 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0359P)2 + 0.8502P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
4499 reflectionsΔρmax = 0.31 e Å3
362 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0131 (8)
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
xyzUiso*/Ueq
S10.08868 (6)0.17279 (3)0.30762 (3)0.02018 (12)
Cl10.35142 (6)0.35743 (4)0.37594 (4)0.03067 (13)
Cl20.26169 (7)0.60192 (4)0.39889 (4)0.04035 (15)
O10.02185 (18)0.07327 (10)0.30945 (9)0.0259 (3)
O20.27445 (17)0.20842 (11)0.35291 (9)0.0263 (3)
N10.0283 (2)0.26300 (13)0.36202 (11)0.0229 (3)
N20.1022 (2)0.12808 (13)0.11187 (11)0.0254 (3)
C10.0953 (2)0.16562 (14)0.18517 (12)0.0204 (4)
C20.0697 (2)0.12792 (14)0.12399 (13)0.0225 (4)
H20.18090.11140.14960.027*
C30.0672 (2)0.11534 (14)0.02583 (13)0.0225 (4)
H30.17700.09040.01470.027*
C40.1003 (3)0.13999 (14)0.01325 (13)0.0212 (4)
C50.2642 (2)0.18018 (15)0.04933 (13)0.0246 (4)
H50.37530.19880.02450.030*
C60.2616 (2)0.19229 (15)0.14784 (13)0.0250 (4)
H60.37090.21820.18890.030*
C70.0135 (2)0.37062 (14)0.36564 (12)0.0215 (4)
C80.1280 (2)0.42513 (15)0.37484 (12)0.0222 (4)
C90.0885 (3)0.53259 (15)0.38279 (13)0.0252 (4)
C100.0889 (3)0.58607 (16)0.37850 (14)0.0292 (4)
H100.11430.65760.38290.035*
C110.2270 (3)0.53155 (16)0.36767 (15)0.0311 (4)
H110.34660.56670.36400.037*
C120.1919 (3)0.42551 (16)0.36219 (14)0.0281 (4)
H120.28800.39070.35620.034*
S210.34092 (6)0.16528 (4)0.19697 (3)0.02337 (13)
Cl210.22476 (7)0.35848 (4)0.15513 (4)0.03547 (14)
Cl220.29998 (7)0.60365 (4)0.13093 (4)0.04141 (15)
O210.30338 (19)0.06822 (11)0.19214 (10)0.0313 (3)
O220.50393 (18)0.19703 (12)0.15791 (10)0.0324 (3)
N210.1609 (2)0.26069 (13)0.13586 (11)0.0242 (3)
N220.3854 (2)0.11132 (14)0.61912 (12)0.0276 (4)
C210.3486 (2)0.15571 (14)0.32033 (13)0.0223 (4)
C220.2263 (3)0.10562 (16)0.38138 (14)0.0272 (4)
H220.13690.08200.35560.033*
C230.2383 (3)0.09120 (15)0.48017 (14)0.0274 (4)
H230.15590.05830.52090.033*
C240.3736 (2)0.12579 (14)0.51956 (13)0.0222 (4)
C250.4928 (3)0.17778 (15)0.45735 (14)0.0264 (4)
H250.58100.20270.48270.032*
C260.4809 (3)0.19254 (15)0.35830 (13)0.0257 (4)
H260.56110.22700.31710.031*
C270.1299 (3)0.36903 (15)0.13061 (12)0.0235 (4)
C280.0471 (3)0.42434 (15)0.13695 (13)0.0241 (4)
C290.0795 (3)0.53256 (15)0.12685 (13)0.0272 (4)
C300.0619 (3)0.58495 (17)0.11441 (15)0.0337 (5)
H300.03970.65660.10950.040*
C310.2365 (3)0.52976 (17)0.10936 (16)0.0370 (5)
H310.33290.56450.10140.044*
C320.2711 (3)0.42338 (17)0.11590 (15)0.0321 (4)
H320.38950.38800.11040.039*
H10.131 (3)0.2370 (19)0.3681 (17)0.035*
H2A0.019 (3)0.075 (2)0.1514 (17)0.035*
H2B0.209 (3)0.1316 (19)0.1340 (17)0.035*
H210.070 (3)0.2365 (19)0.1320 (17)0.035*
H22A0.483 (3)0.1184 (19)0.6416 (17)0.035*
H22B0.337 (3)0.062 (2)0.6560 (17)0.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0216 (2)0.0209 (2)0.0187 (2)0.00647 (18)0.00095 (16)0.00723 (17)
Cl10.0174 (2)0.0302 (3)0.0442 (3)0.00384 (19)0.00067 (18)0.0145 (2)
Cl20.0344 (3)0.0317 (3)0.0575 (3)0.0164 (2)0.0006 (2)0.0147 (2)
O10.0320 (7)0.0224 (7)0.0251 (6)0.0071 (6)0.0046 (5)0.0106 (5)
O20.0230 (7)0.0314 (7)0.0252 (6)0.0088 (6)0.0021 (5)0.0099 (5)
N10.0203 (8)0.0210 (8)0.0262 (8)0.0041 (6)0.0043 (6)0.0077 (6)
N20.0288 (8)0.0242 (9)0.0212 (8)0.0036 (7)0.0024 (7)0.0076 (6)
C10.0248 (9)0.0186 (9)0.0188 (8)0.0064 (7)0.0020 (7)0.0074 (7)
C20.0204 (9)0.0216 (9)0.0259 (9)0.0043 (7)0.0025 (7)0.0095 (7)
C30.0228 (9)0.0184 (9)0.0247 (9)0.0021 (7)0.0034 (7)0.0079 (7)
C40.0282 (9)0.0134 (8)0.0225 (8)0.0054 (7)0.0012 (7)0.0071 (7)
C50.0205 (9)0.0257 (10)0.0270 (9)0.0038 (7)0.0051 (7)0.0098 (8)
C60.0197 (9)0.0274 (10)0.0248 (9)0.0032 (8)0.0022 (7)0.0075 (7)
C70.0229 (9)0.0216 (9)0.0182 (8)0.0042 (7)0.0001 (7)0.0058 (7)
C80.0182 (8)0.0239 (10)0.0212 (8)0.0019 (7)0.0013 (6)0.0061 (7)
C90.0262 (9)0.0243 (10)0.0247 (9)0.0091 (8)0.0025 (7)0.0066 (7)
C100.0317 (10)0.0217 (10)0.0304 (10)0.0019 (8)0.0026 (8)0.0077 (8)
C110.0219 (9)0.0276 (11)0.0401 (11)0.0015 (8)0.0011 (8)0.0123 (9)
C120.0211 (9)0.0275 (11)0.0347 (10)0.0076 (8)0.0030 (8)0.0093 (8)
S210.0210 (2)0.0257 (3)0.0222 (2)0.00013 (18)0.00040 (17)0.01065 (18)
Cl210.0251 (2)0.0304 (3)0.0545 (3)0.0101 (2)0.0102 (2)0.0177 (2)
Cl220.0361 (3)0.0308 (3)0.0547 (3)0.0023 (2)0.0015 (2)0.0186 (2)
O210.0357 (8)0.0270 (7)0.0308 (7)0.0017 (6)0.0052 (6)0.0153 (6)
O220.0220 (7)0.0434 (9)0.0303 (7)0.0027 (6)0.0054 (5)0.0145 (6)
N210.0210 (8)0.0233 (9)0.0273 (8)0.0037 (7)0.0040 (6)0.0091 (6)
N220.0281 (9)0.0302 (9)0.0244 (8)0.0044 (7)0.0007 (7)0.0112 (7)
C210.0218 (9)0.0222 (9)0.0226 (9)0.0014 (7)0.0014 (7)0.0099 (7)
C220.0241 (9)0.0320 (11)0.0289 (10)0.0083 (8)0.0007 (7)0.0142 (8)
C230.0274 (10)0.0289 (11)0.0285 (9)0.0094 (8)0.0064 (8)0.0118 (8)
C240.0218 (9)0.0182 (9)0.0244 (9)0.0027 (7)0.0015 (7)0.0094 (7)
C250.0233 (9)0.0276 (10)0.0295 (10)0.0057 (8)0.0031 (7)0.0120 (8)
C260.0244 (9)0.0247 (10)0.0273 (9)0.0069 (8)0.0017 (7)0.0081 (8)
C270.0254 (9)0.0235 (10)0.0192 (8)0.0043 (8)0.0028 (7)0.0060 (7)
C280.0247 (9)0.0248 (10)0.0228 (9)0.0084 (8)0.0000 (7)0.0071 (7)
C290.0296 (10)0.0237 (10)0.0254 (9)0.0015 (8)0.0031 (7)0.0082 (8)
C300.0414 (12)0.0239 (11)0.0341 (11)0.0088 (9)0.0048 (9)0.0080 (8)
C310.0350 (11)0.0320 (12)0.0450 (12)0.0167 (9)0.0035 (9)0.0105 (9)
C320.0234 (10)0.0327 (11)0.0383 (11)0.0073 (8)0.0018 (8)0.0105 (9)
Geometric parameters (Å, º) top
S1—O21.4357 (13)S21—O211.4335 (14)
S1—O11.4363 (14)S21—O221.4338 (14)
S1—N11.6363 (16)S21—N211.6400 (16)
S1—C11.7507 (17)S21—C211.7519 (17)
Cl1—C81.7276 (18)Cl21—C281.7274 (18)
Cl2—C91.7299 (18)Cl22—C291.735 (2)
N1—C71.412 (2)N21—C271.417 (2)
N1—H10.79 (2)N21—H210.82 (2)
N2—C41.386 (2)N22—C241.390 (2)
N2—H2A0.86 (3)N22—H22A0.83 (3)
N2—H2B0.86 (2)N22—H22B0.84 (2)
C1—C61.389 (3)C21—C261.391 (3)
C1—C21.399 (2)C21—C221.392 (3)
C2—C31.377 (2)C22—C231.379 (3)
C2—H20.9300C22—H220.9300
C3—C41.403 (3)C23—C241.400 (3)
C3—H30.9300C23—H230.9300
C4—C51.401 (3)C24—C251.393 (3)
C5—C61.384 (3)C25—C261.381 (3)
C5—H50.9300C25—H250.9300
C6—H60.9300C26—H260.9300
C7—C121.391 (3)C27—C321.391 (3)
C7—C81.398 (3)C27—C281.395 (3)
C8—C91.390 (3)C28—C291.394 (3)
C9—C101.381 (3)C29—C301.376 (3)
C10—C111.375 (3)C30—C311.375 (3)
C10—H100.9300C30—H300.9300
C11—C121.383 (3)C31—C321.383 (3)
C11—H110.9300C31—H310.9300
C12—H120.9300C32—H320.9300
O2—S1—O1118.26 (8)O21—S21—O22118.74 (9)
O2—S1—N1109.94 (8)O21—S21—N21104.51 (8)
O1—S1—N1104.31 (8)O22—S21—N21108.70 (8)
O2—S1—C1107.97 (8)O21—S21—C21108.99 (8)
O1—S1—C1109.34 (8)O22—S21—C21107.39 (8)
N1—S1—C1106.43 (8)N21—S21—C21108.11 (8)
C7—N1—S1124.90 (13)C27—N21—S21123.94 (13)
C7—N1—H1118.1 (17)C27—N21—H21117.8 (16)
S1—N1—H1113.1 (17)S21—N21—H21112.2 (16)
C4—N2—H2A115.0 (15)C24—N22—H22A115.9 (16)
C4—N2—H2B115.2 (15)C24—N22—H22B115.4 (16)
H2A—N2—H2B113 (2)H22A—N22—H22B117 (2)
C6—C1—C2120.33 (16)C26—C21—C22120.27 (16)
C6—C1—S1120.87 (14)C26—C21—S21120.62 (14)
C2—C1—S1118.75 (13)C22—C21—S21119.03 (14)
C3—C2—C1119.93 (16)C23—C22—C21119.78 (17)
C3—C2—H2120.0C23—C22—H22120.1
C1—C2—H2120.0C21—C22—H22120.1
C2—C3—C4120.29 (16)C22—C23—C24120.37 (17)
C2—C3—H3119.9C22—C23—H23119.8
C4—C3—H3119.9C24—C23—H23119.8
N2—C4—C5120.61 (17)N22—C24—C25120.32 (17)
N2—C4—C3120.13 (16)N22—C24—C23120.32 (17)
C5—C4—C3119.22 (16)C25—C24—C23119.33 (16)
C6—C5—C4120.44 (16)C26—C25—C24120.39 (17)
C6—C5—H5119.8C26—C25—H25119.8
C4—C5—H5119.8C24—C25—H25119.8
C5—C6—C1119.76 (16)C25—C26—C21119.83 (17)
C5—C6—H6120.1C25—C26—H26120.1
C1—C6—H6120.1C21—C26—H26120.1
C12—C7—C8118.48 (17)C32—C27—C28118.77 (17)
C12—C7—N1122.30 (16)C32—C27—N21121.48 (17)
C8—C7—N1119.21 (16)C28—C27—N21119.72 (16)
C9—C8—C7120.09 (16)C29—C28—C27119.76 (17)
C9—C8—Cl1120.64 (14)C29—C28—Cl21120.66 (15)
C7—C8—Cl1119.28 (14)C27—C28—Cl21119.58 (14)
C10—C9—C8120.93 (17)C30—C29—C28121.01 (18)
C10—C9—Cl2118.80 (15)C30—C29—Cl22118.63 (15)
C8—C9—Cl2120.27 (14)C28—C29—Cl22120.36 (15)
C11—C10—C9118.76 (18)C31—C30—C29119.00 (19)
C11—C10—H10120.6C31—C30—H30120.5
C9—C10—H10120.6C29—C30—H30120.5
C10—C11—C12121.35 (18)C30—C31—C32121.10 (19)
C10—C11—H11119.3C30—C31—H31119.5
C12—C11—H11119.3C32—C31—H31119.5
C11—C12—C7120.36 (18)C31—C32—C27120.31 (19)
C11—C12—H12119.8C31—C32—H32119.8
C7—C12—H12119.8C27—C32—H32119.8
O2—S1—N1—C761.42 (16)O21—S21—N21—C27173.03 (15)
O1—S1—N1—C7170.83 (14)O22—S21—N21—C2759.24 (17)
C1—S1—N1—C755.27 (16)C21—S21—N21—C2757.04 (17)
O2—S1—C1—C60.04 (18)O21—S21—C21—C26139.32 (15)
O1—S1—C1—C6129.93 (15)O22—S21—C21—C269.49 (18)
N1—S1—C1—C6117.95 (16)N21—S21—C21—C26107.64 (16)
O2—S1—C1—C2177.19 (13)O21—S21—C21—C2237.43 (17)
O1—S1—C1—C247.30 (16)O22—S21—C21—C22167.26 (15)
N1—S1—C1—C264.82 (16)N21—S21—C21—C2275.61 (17)
C6—C1—C2—C31.1 (3)C26—C21—C22—C230.9 (3)
S1—C1—C2—C3176.11 (13)S21—C21—C22—C23175.85 (15)
C1—C2—C3—C40.1 (3)C21—C22—C23—C240.6 (3)
C2—C3—C4—N2179.46 (16)C22—C23—C24—N22179.93 (17)
C2—C3—C4—C51.7 (3)C22—C23—C24—C251.9 (3)
N2—C4—C5—C6179.78 (17)N22—C24—C25—C26179.78 (17)
C3—C4—C5—C62.0 (3)C23—C24—C25—C261.7 (3)
C4—C5—C6—C10.8 (3)C24—C25—C26—C210.3 (3)
C2—C1—C6—C50.8 (3)C22—C21—C26—C251.1 (3)
S1—C1—C6—C5176.38 (14)S21—C21—C26—C25175.65 (14)
S1—N1—C7—C1228.1 (2)S21—N21—C27—C3243.0 (2)
S1—N1—C7—C8153.10 (14)S21—N21—C27—C28139.22 (15)
C12—C7—C8—C91.6 (3)C32—C27—C28—C291.1 (3)
N1—C7—C8—C9177.24 (16)N21—C27—C28—C29176.81 (16)
C12—C7—C8—Cl1178.28 (13)C32—C27—C28—Cl21179.96 (14)
N1—C7—C8—Cl12.9 (2)N21—C27—C28—Cl212.1 (2)
C7—C8—C9—C102.1 (3)C27—C28—C29—C302.5 (3)
Cl1—C8—C9—C10177.72 (14)Cl21—C28—C29—C30178.63 (15)
C7—C8—C9—Cl2177.55 (13)C27—C28—C29—Cl22178.12 (14)
Cl1—C8—C9—Cl22.6 (2)Cl21—C28—C29—Cl220.8 (2)
C8—C9—C10—C111.0 (3)C28—C29—C30—C311.7 (3)
Cl2—C9—C10—C11178.73 (15)Cl22—C29—C30—C31178.87 (16)
C9—C10—C11—C120.7 (3)C29—C30—C31—C320.4 (3)
C10—C11—C12—C71.3 (3)C30—C31—C32—C271.8 (3)
C8—C7—C12—C110.1 (3)C28—C27—C32—C311.0 (3)
N1—C7—C12—C11178.87 (17)N21—C27—C32—C31178.88 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N22i0.79 (2)2.33 (3)3.083 (2)160 (2)
N2—H2a···O1ii0.86 (3)2.47 (2)3.126 (2)134 (2)
N2—H2a···O21ii0.86 (3)2.45 (2)3.066 (2)130 (2)
N2—H2b···O22iii0.86 (2)2.22 (3)3.047 (2)161 (2)
N21—H21···N2ii0.82 (2)2.25 (3)3.034 (2)160 (2)
N22—H22a···O2iv0.83 (2)2.41 (3)3.190 (2)156 (2)
N22—H22a···O21iv0.83 (2)2.94 (2)3.401 (2)117 (2)
N22—H22b···O1i0.84 (2)2.40 (2)2.999 (2)129 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z; (iii) x+1, y, z; (iv) x+1, y, z+1.
 

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