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The title compound, C
12H
10Cl
2N
2O
2S, 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 NH
2 and SO
2 groups link molecules into layers.
Supporting information
CCDC reference: 640498
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C12H10Cl2N2O2S | F(000) = 648 |
Mr = 317.18 | Dx = 1.565 Mg m−3 |
Monoclinic, P21/c | Melting point: 445.9 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.848 (2) Å | Cell parameters from 35 reflections |
b = 7.262 (1) Å | θ = 5–12° |
c = 14.993 (2) Å | µ = 0.64 mm−1 |
β = 105.72 (1)° | T = 293 K |
V = 1346.4 (3) Å3 | Prism, colourless |
Z = 4 | 0.27 × 0.18 × 0.13 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.028 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.8° |
Graphite monochromator | h = −1→15 |
ω–2θ scans | k = −6→1 |
2895 measured reflections | l = −17→17 |
2149 independent reflections | 3 standard reflections every 2 reflections |
1527 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H 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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
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 | 0.84308 (6) | −0.05717 (12) | 0.66931 (5) | 0.0341 (2) | |
Cl1 | 0.66308 (7) | 0.41651 (13) | 0.66620 (7) | 0.0559 (3) | |
Cl2 | 0.40148 (7) | −0.31261 (15) | 0.59089 (7) | 0.0652 (3) | |
O1 | 0.93778 (16) | 0.0139 (3) | 0.64738 (16) | 0.0455 (6) | |
O2 | 0.81610 (18) | −0.2471 (3) | 0.65326 (15) | 0.0432 (6) | |
N1 | 0.7434 (2) | 0.0642 (4) | 0.60458 (18) | 0.0347 (7) | |
N2 | 0.8767 (2) | 0.1040 (5) | 1.06307 (19) | 0.0427 (8) | |
C1 | 0.8508 (2) | −0.0105 (4) | 0.7855 (2) | 0.0316 (7) | |
C2 | 0.8898 (2) | 0.1593 (5) | 0.8230 (2) | 0.0374 (8) | |
H2 | 0.9098 | 0.2481 | 0.7861 | 0.045* | |
C3 | 0.8986 (2) | 0.1953 (5) | 0.9150 (2) | 0.0368 (8) | |
H3 | 0.9250 | 0.3087 | 0.9401 | 0.044* | |
C4 | 0.8684 (2) | 0.0644 (5) | 0.9707 (2) | 0.0339 (8) | |
C5 | 0.8277 (3) | −0.1034 (5) | 0.9319 (2) | 0.0406 (8) | |
H5 | 0.8059 | −0.1912 | 0.9682 | 0.049* | |
C6 | 0.8194 (3) | −0.1407 (5) | 0.8400 (2) | 0.0401 (8) | |
H6 | 0.7925 | −0.2537 | 0.8148 | 0.048* | |
C7 | 0.6379 (2) | 0.0563 (5) | 0.6189 (2) | 0.0338 (8) | |
C8 | 0.5909 (3) | 0.2121 (5) | 0.6451 (2) | 0.0412 (8) | |
C9 | 0.4859 (3) | 0.2068 (6) | 0.6533 (2) | 0.0509 (10) | |
H9 | 0.4544 | 0.3125 | 0.6695 | 0.061* | |
C10 | 0.4290 (3) | 0.0461 (6) | 0.6373 (2) | 0.0516 (10) | |
H10 | 0.3587 | 0.0422 | 0.6430 | 0.062* | |
C11 | 0.4750 (3) | −0.1098 (5) | 0.6129 (2) | 0.0450 (9) | |
C12 | 0.5799 (2) | −0.1063 (5) | 0.6020 (2) | 0.0375 (8) | |
H12 | 0.6099 | −0.2115 | 0.5837 | 0.045* | |
H2A | 0.923 (3) | 0.186 (5) | 1.090 (2) | 0.045* | |
H2B | 0.871 (3) | 0.012 (5) | 1.093 (2) | 0.045* | |
H1 | 0.761 (3) | 0.162 (5) | 0.596 (2) | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0313 (4) | 0.0355 (6) | 0.0366 (4) | 0.0029 (4) | 0.0111 (3) | 0.0001 (4) |
Cl1 | 0.0540 (6) | 0.0468 (6) | 0.0710 (6) | −0.0018 (5) | 0.0242 (5) | −0.0135 (5) |
Cl2 | 0.0433 (5) | 0.0667 (8) | 0.0766 (7) | −0.0188 (5) | 0.0008 (5) | 0.0164 (5) |
O1 | 0.0333 (12) | 0.0534 (16) | 0.0559 (14) | 0.0036 (11) | 0.0224 (11) | 0.0061 (12) |
O2 | 0.0518 (14) | 0.0301 (15) | 0.0499 (14) | 0.0014 (11) | 0.0177 (11) | −0.0057 (11) |
N1 | 0.0325 (14) | 0.0361 (18) | 0.0363 (14) | 0.0006 (13) | 0.0105 (11) | 0.0051 (13) |
N2 | 0.0421 (17) | 0.047 (2) | 0.0397 (17) | 0.0003 (15) | 0.0118 (13) | 0.0007 (14) |
C1 | 0.0274 (15) | 0.032 (2) | 0.0350 (16) | −0.0022 (14) | 0.0077 (13) | 0.0010 (14) |
C2 | 0.0383 (18) | 0.035 (2) | 0.0377 (18) | −0.0035 (16) | 0.0089 (14) | 0.0042 (15) |
C3 | 0.0367 (17) | 0.031 (2) | 0.0391 (18) | −0.0021 (15) | 0.0047 (14) | −0.0041 (15) |
C4 | 0.0238 (15) | 0.043 (2) | 0.0342 (16) | 0.0068 (15) | 0.0071 (13) | 0.0030 (15) |
C5 | 0.0421 (18) | 0.043 (2) | 0.0389 (18) | −0.0060 (17) | 0.0144 (15) | 0.0043 (16) |
C6 | 0.0419 (19) | 0.033 (2) | 0.0446 (19) | −0.0070 (16) | 0.0105 (15) | −0.0019 (15) |
C7 | 0.0291 (16) | 0.041 (2) | 0.0296 (15) | −0.0007 (16) | 0.0050 (13) | 0.0054 (15) |
C8 | 0.0394 (19) | 0.047 (2) | 0.0388 (19) | 0.0024 (17) | 0.0131 (15) | 0.0013 (16) |
C9 | 0.041 (2) | 0.061 (3) | 0.056 (2) | 0.007 (2) | 0.0220 (17) | −0.0002 (19) |
C10 | 0.0329 (18) | 0.074 (3) | 0.051 (2) | 0.001 (2) | 0.0157 (16) | 0.010 (2) |
C11 | 0.0348 (18) | 0.053 (3) | 0.0412 (19) | −0.0081 (18) | 0.0007 (15) | 0.0140 (17) |
C12 | 0.0315 (17) | 0.042 (2) | 0.0358 (17) | 0.0023 (16) | 0.0040 (13) | 0.0070 (15) |
Geometric parameters (Å, º) top
S—O2 | 1.427 (2) | C3—C4 | 1.388 (4) |
S—O1 | 1.439 (2) | C3—H3 | 0.9300 |
S—N1 | 1.639 (3) | C4—C5 | 1.390 (5) |
S—C1 | 1.751 (3) | C5—C6 | 1.380 (4) |
Cl1—C8 | 1.733 (4) | C5—H5 | 0.9300 |
Cl2—C11 | 1.732 (4) | C6—H6 | 0.9300 |
N1—C7 | 1.430 (4) | C7—C12 | 1.382 (5) |
N1—H1 | 0.77 (4) | C7—C8 | 1.388 (4) |
N2—C4 | 1.390 (4) | C8—C9 | 1.389 (5) |
N2—H2A | 0.86 (4) | C9—C10 | 1.363 (5) |
N2—H2B | 0.82 (4) | C9—H9 | 0.9300 |
C1—C6 | 1.379 (4) | C10—C11 | 1.372 (5) |
C1—C2 | 1.391 (5) | C10—H10 | 0.9300 |
C2—C3 | 1.379 (4) | C11—C12 | 1.400 (4) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
| | | |
O2—S—O1 | 119.35 (14) | C6—C5—C4 | 120.5 (3) |
O2—S—N1 | 107.74 (15) | C6—C5—H5 | 119.7 |
O1—S—N1 | 104.21 (14) | C4—C5—H5 | 119.7 |
O2—S—C1 | 107.49 (14) | C1—C6—C5 | 120.1 (3) |
O1—S—C1 | 109.51 (14) | C1—C6—H6 | 120.0 |
N1—S—C1 | 108.05 (14) | C5—C6—H6 | 120.0 |
C7—N1—S | 120.7 (2) | C12—C7—C8 | 119.6 (3) |
C7—N1—H1 | 114 (3) | C12—C7—N1 | 119.5 (3) |
S—N1—H1 | 112 (3) | C8—C7—N1 | 120.8 (3) |
C4—N2—H2A | 118 (2) | C7—C8—C9 | 120.7 (3) |
C4—N2—H2B | 112 (3) | C7—C8—Cl1 | 119.9 (2) |
H2A—N2—H2B | 118 (4) | C9—C8—Cl1 | 119.5 (3) |
C6—C1—C2 | 120.0 (3) | C10—C9—C8 | 119.7 (4) |
C6—C1—S | 120.7 (2) | C10—C9—H9 | 120.2 |
C2—C1—S | 119.4 (2) | C8—C9—H9 | 120.2 |
C3—C2—C1 | 119.7 (3) | C9—C10—C11 | 120.3 (3) |
C3—C2—H2 | 120.1 | C9—C10—H10 | 119.9 |
C1—C2—H2 | 120.1 | C11—C10—H10 | 119.9 |
C2—C3—C4 | 120.7 (3) | C10—C11—C12 | 120.9 (3) |
C2—C3—H3 | 119.6 | C10—C11—Cl2 | 120.0 (3) |
C4—C3—H3 | 119.6 | C12—C11—Cl2 | 119.0 (3) |
C3—C4—C5 | 119.0 (3) | C7—C12—C11 | 118.8 (3) |
C3—C4—N2 | 119.9 (3) | C7—C12—H12 | 120.6 |
C5—C4—N2 | 121.1 (3) | C11—C12—H12 | 120.6 |
| | | |
O2—S—N1—C7 | 63.5 (3) | S—C1—C6—C5 | 178.8 (2) |
O1—S—N1—C7 | −168.8 (3) | C4—C5—C6—C1 | −0.5 (5) |
C1—S—N1—C7 | −52.4 (3) | S—N1—C7—C12 | −65.9 (3) |
O2—S—C1—C6 | −7.9 (3) | S—N1—C7—C8 | 117.4 (3) |
O1—S—C1—C6 | −139.0 (3) | C12—C7—C8—C9 | −0.9 (5) |
N1—S—C1—C6 | 108.1 (3) | N1—C7—C8—C9 | 175.9 (3) |
O2—S—C1—C2 | 171.6 (2) | C12—C7—C8—Cl1 | −179.9 (2) |
O1—S—C1—C2 | 40.6 (3) | N1—C7—C8—Cl1 | −3.1 (4) |
N1—S—C1—C2 | −72.4 (3) | C7—C8—C9—C10 | 1.4 (5) |
C6—C1—C2—C3 | 1.2 (5) | Cl1—C8—C9—C10 | −179.6 (3) |
S—C1—C2—C3 | −178.4 (2) | C8—C9—C10—C11 | −0.3 (5) |
C1—C2—C3—C4 | −0.3 (5) | C9—C10—C11—C12 | −1.4 (5) |
C2—C3—C4—C5 | −0.9 (5) | C9—C10—C11—Cl2 | −178.9 (3) |
C2—C3—C4—N2 | −179.3 (3) | C8—C7—C12—C11 | −0.8 (4) |
C3—C4—C5—C6 | 1.3 (5) | N1—C7—C12—C11 | −177.5 (3) |
N2—C4—C5—C6 | 179.7 (3) | C10—C11—C12—C7 | 1.9 (5) |
C2—C1—C6—C5 | −0.7 (5) | Cl2—C11—C12—C7 | 179.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.74 (4) | 2.394 (4) | 3.116 (4) | 157 (4) |
N2—H2a···O1ii | 0.86 (4) | 2.33 (1) | 3.062 (4) | 143 (3) |
N2—H2b···O2iii | 0.82 (4) | 2.32 (1) | 3.118 (4) | 166 (3) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y−1/2, z+1/2. |
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