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The title compound, C12H10Cl2N2O2S, was crystallized from a water–ethanol mixture. The dihedral angle between the two benzene rings is 64.86 (11)°. N—H...O and N—H...N hydrogen bonds between the NH2 and SO2 groups link mol­ecules into layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008744/sj2228sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008744/sj2228Isup2.hkl
Contains datablock I

CCDC reference: 640498

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.105
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Author Response: Due to not so good quality of the single crystal. For this compound it is very difficult to prepare the single crystals.

PLAT736_ALERT_1_A H...A   Calc     2.40(4), Rep    2.394(4) ......       9.90 su-Ra
              H1   -N2      1.555   4.565
PLAT736_ALERT_1_A H...A   Calc     2.33(4), Rep    2.331(4) ......       9.90 su-Ra
              H2A  -O1      1.555   4.566
PLAT736_ALERT_1_A H...A   Calc     2.32(4), Rep    2.317(4) ......       9.90 su-Ra
              H2B  -O2      1.555   4.556

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 2149 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2367 Completeness (_total/calc) 90.79% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O2 .. 3.17 Ang.
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2149 From the CIF: _diffrn_reflns_limit_ max hkl 15. 1. 17. From the CIF: _diffrn_reflns_limit_ min hkl -1. -6. -17. TEST1: Expected hkl limits for theta max Calculated maximum hkl 15. 8. 17. Calculated minimum hkl -15. -8. -17. PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
4 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 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: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

4-Amino-N-(2,5-dichlorophenyl)benzenesulfonamide top
Crystal data top
C12H10Cl2N2O2SF(000) = 648
Mr = 317.18Dx = 1.565 Mg m3
Monoclinic, P21/cMelting point: 445.9 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.848 (2) ÅCell parameters from 35 reflections
b = 7.262 (1) Åθ = 5–12°
c = 14.993 (2) ŵ = 0.64 mm1
β = 105.72 (1)°T = 293 K
V = 1346.4 (3) Å3Prism, colourless
Z = 40.27 × 0.18 × 0.13 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.028
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.8°
Graphite monochromatorh = 115
ω–2θ scansk = 61
2895 measured reflectionsl = 1717
2149 independent reflections3 standard reflections every 2 reflections
1527 reflections with I > 2σ(I) intensity decay: none
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.3454P]
where P = (Fo2 + 2Fc2)/3
2149 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.42 e Å3
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
S0.84308 (6)0.05717 (12)0.66931 (5)0.0341 (2)
Cl10.66308 (7)0.41651 (13)0.66620 (7)0.0559 (3)
Cl20.40148 (7)0.31261 (15)0.59089 (7)0.0652 (3)
O10.93778 (16)0.0139 (3)0.64738 (16)0.0455 (6)
O20.81610 (18)0.2471 (3)0.65326 (15)0.0432 (6)
N10.7434 (2)0.0642 (4)0.60458 (18)0.0347 (7)
N20.8767 (2)0.1040 (5)1.06307 (19)0.0427 (8)
C10.8508 (2)0.0105 (4)0.7855 (2)0.0316 (7)
C20.8898 (2)0.1593 (5)0.8230 (2)0.0374 (8)
H20.90980.24810.78610.045*
C30.8986 (2)0.1953 (5)0.9150 (2)0.0368 (8)
H30.92500.30870.94010.044*
C40.8684 (2)0.0644 (5)0.9707 (2)0.0339 (8)
C50.8277 (3)0.1034 (5)0.9319 (2)0.0406 (8)
H50.80590.19120.96820.049*
C60.8194 (3)0.1407 (5)0.8400 (2)0.0401 (8)
H60.79250.25370.81480.048*
C70.6379 (2)0.0563 (5)0.6189 (2)0.0338 (8)
C80.5909 (3)0.2121 (5)0.6451 (2)0.0412 (8)
C90.4859 (3)0.2068 (6)0.6533 (2)0.0509 (10)
H90.45440.31250.66950.061*
C100.4290 (3)0.0461 (6)0.6373 (2)0.0516 (10)
H100.35870.04220.64300.062*
C110.4750 (3)0.1098 (5)0.6129 (2)0.0450 (9)
C120.5799 (2)0.1063 (5)0.6020 (2)0.0375 (8)
H120.60990.21150.58370.045*
H2A0.923 (3)0.186 (5)1.090 (2)0.045*
H2B0.871 (3)0.012 (5)1.093 (2)0.045*
H10.761 (3)0.162 (5)0.596 (2)0.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0313 (4)0.0355 (6)0.0366 (4)0.0029 (4)0.0111 (3)0.0001 (4)
Cl10.0540 (6)0.0468 (6)0.0710 (6)0.0018 (5)0.0242 (5)0.0135 (5)
Cl20.0433 (5)0.0667 (8)0.0766 (7)0.0188 (5)0.0008 (5)0.0164 (5)
O10.0333 (12)0.0534 (16)0.0559 (14)0.0036 (11)0.0224 (11)0.0061 (12)
O20.0518 (14)0.0301 (15)0.0499 (14)0.0014 (11)0.0177 (11)0.0057 (11)
N10.0325 (14)0.0361 (18)0.0363 (14)0.0006 (13)0.0105 (11)0.0051 (13)
N20.0421 (17)0.047 (2)0.0397 (17)0.0003 (15)0.0118 (13)0.0007 (14)
C10.0274 (15)0.032 (2)0.0350 (16)0.0022 (14)0.0077 (13)0.0010 (14)
C20.0383 (18)0.035 (2)0.0377 (18)0.0035 (16)0.0089 (14)0.0042 (15)
C30.0367 (17)0.031 (2)0.0391 (18)0.0021 (15)0.0047 (14)0.0041 (15)
C40.0238 (15)0.043 (2)0.0342 (16)0.0068 (15)0.0071 (13)0.0030 (15)
C50.0421 (18)0.043 (2)0.0389 (18)0.0060 (17)0.0144 (15)0.0043 (16)
C60.0419 (19)0.033 (2)0.0446 (19)0.0070 (16)0.0105 (15)0.0019 (15)
C70.0291 (16)0.041 (2)0.0296 (15)0.0007 (16)0.0050 (13)0.0054 (15)
C80.0394 (19)0.047 (2)0.0388 (19)0.0024 (17)0.0131 (15)0.0013 (16)
C90.041 (2)0.061 (3)0.056 (2)0.007 (2)0.0220 (17)0.0002 (19)
C100.0329 (18)0.074 (3)0.051 (2)0.001 (2)0.0157 (16)0.010 (2)
C110.0348 (18)0.053 (3)0.0412 (19)0.0081 (18)0.0007 (15)0.0140 (17)
C120.0315 (17)0.042 (2)0.0358 (17)0.0023 (16)0.0040 (13)0.0070 (15)
Geometric parameters (Å, º) top
S—O21.427 (2)C3—C41.388 (4)
S—O11.439 (2)C3—H30.9300
S—N11.639 (3)C4—C51.390 (5)
S—C11.751 (3)C5—C61.380 (4)
Cl1—C81.733 (4)C5—H50.9300
Cl2—C111.732 (4)C6—H60.9300
N1—C71.430 (4)C7—C121.382 (5)
N1—H10.77 (4)C7—C81.388 (4)
N2—C41.390 (4)C8—C91.389 (5)
N2—H2A0.86 (4)C9—C101.363 (5)
N2—H2B0.82 (4)C9—H90.9300
C1—C61.379 (4)C10—C111.372 (5)
C1—C21.391 (5)C10—H100.9300
C2—C31.379 (4)C11—C121.400 (4)
C2—H20.9300C12—H120.9300
O2—S—O1119.35 (14)C6—C5—C4120.5 (3)
O2—S—N1107.74 (15)C6—C5—H5119.7
O1—S—N1104.21 (14)C4—C5—H5119.7
O2—S—C1107.49 (14)C1—C6—C5120.1 (3)
O1—S—C1109.51 (14)C1—C6—H6120.0
N1—S—C1108.05 (14)C5—C6—H6120.0
C7—N1—S120.7 (2)C12—C7—C8119.6 (3)
C7—N1—H1114 (3)C12—C7—N1119.5 (3)
S—N1—H1112 (3)C8—C7—N1120.8 (3)
C4—N2—H2A118 (2)C7—C8—C9120.7 (3)
C4—N2—H2B112 (3)C7—C8—Cl1119.9 (2)
H2A—N2—H2B118 (4)C9—C8—Cl1119.5 (3)
C6—C1—C2120.0 (3)C10—C9—C8119.7 (4)
C6—C1—S120.7 (2)C10—C9—H9120.2
C2—C1—S119.4 (2)C8—C9—H9120.2
C3—C2—C1119.7 (3)C9—C10—C11120.3 (3)
C3—C2—H2120.1C9—C10—H10119.9
C1—C2—H2120.1C11—C10—H10119.9
C2—C3—C4120.7 (3)C10—C11—C12120.9 (3)
C2—C3—H3119.6C10—C11—Cl2120.0 (3)
C4—C3—H3119.6C12—C11—Cl2119.0 (3)
C3—C4—C5119.0 (3)C7—C12—C11118.8 (3)
C3—C4—N2119.9 (3)C7—C12—H12120.6
C5—C4—N2121.1 (3)C11—C12—H12120.6
O2—S—N1—C763.5 (3)S—C1—C6—C5178.8 (2)
O1—S—N1—C7168.8 (3)C4—C5—C6—C10.5 (5)
C1—S—N1—C752.4 (3)S—N1—C7—C1265.9 (3)
O2—S—C1—C67.9 (3)S—N1—C7—C8117.4 (3)
O1—S—C1—C6139.0 (3)C12—C7—C8—C90.9 (5)
N1—S—C1—C6108.1 (3)N1—C7—C8—C9175.9 (3)
O2—S—C1—C2171.6 (2)C12—C7—C8—Cl1179.9 (2)
O1—S—C1—C240.6 (3)N1—C7—C8—Cl13.1 (4)
N1—S—C1—C272.4 (3)C7—C8—C9—C101.4 (5)
C6—C1—C2—C31.2 (5)Cl1—C8—C9—C10179.6 (3)
S—C1—C2—C3178.4 (2)C8—C9—C10—C110.3 (5)
C1—C2—C3—C40.3 (5)C9—C10—C11—C121.4 (5)
C2—C3—C4—C50.9 (5)C9—C10—C11—Cl2178.9 (3)
C2—C3—C4—N2179.3 (3)C8—C7—C12—C110.8 (4)
C3—C4—C5—C61.3 (5)N1—C7—C12—C11177.5 (3)
N2—C4—C5—C6179.7 (3)C10—C11—C12—C71.9 (5)
C2—C1—C6—C50.7 (5)Cl2—C11—C12—C7179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.74 (4)2.394 (4)3.116 (4)157 (4)
N2—H2a···O1ii0.86 (4)2.33 (1)3.062 (4)143 (3)
N2—H2b···O2iii0.82 (4)2.32 (1)3.118 (4)166 (3)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z+1/2.
 

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