In the molecule of the title compound, C
13H
12N
2O
4S, the two benzene ring planes are nearly orthogonal to one another [dihedral angle = 86.1 (1)°]. The C—N—S—C torsion angle in the central part of the molecule is 65.85 (13)°. The molecular packing is stabilized by intermolecular N—H

O interactions.
Supporting information
CCDC reference: 294006
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.120
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997,); software used to prepare material for publication: SHELXTL.
4-Methyl-
N-(4-nitrophenyl)benzenesulfonamide
top
Crystal data top
C13H12N2O4S | F(000) = 608 |
Mr = 292.31 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 12625 reflections |
a = 13.800 (3) Å | θ = 3.0–27.5° |
b = 8.2320 (16) Å | µ = 0.26 mm−1 |
c = 11.959 (2) Å | T = 293 K |
β = 103.36 (3)° | Block, light-yellow |
V = 1321.8 (5) Å3 | 0.59 × 0.45 × 0.31 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID IP area-detector diffractometer | 3031 independent reflections |
Radiation source: rotating anode | 2669 reflections with I > 2˘I) |
Graphite monochromator | Rint = 0.031 |
oscillation scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995) | h = −17→17 |
Tmin = 0.861, Tmax = 0.924 | k = −10→10 |
12625 measured reflections | l = −15→15 |
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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0789P)2 + 0.2786P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.043 |
3031 reflections | Δρmax = 0.38 e Å−3 |
182 parameters | Δρmin = −0.36 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: 0.055 (4) |
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 | |
S1 | 0.26167 (3) | 0.17491 (4) | 0.73381 (3) | 0.03660 (15) | |
N1 | 0.08112 (9) | −0.48378 (15) | 0.41140 (11) | 0.0402 (3) | |
N2 | 0.16868 (9) | 0.11925 (15) | 0.62936 (11) | 0.0395 (3) | |
H2A | 0.1237 | 0.1912 | 0.6043 | 0.047* | |
C1 | 0.11026 (10) | −0.32824 (16) | 0.46813 (12) | 0.0337 (3) | |
C2 | 0.15781 (12) | −0.32639 (17) | 0.58264 (13) | 0.0399 (3) | |
H2B | 0.1747 | −0.4231 | 0.6226 | 0.048* | |
C3 | 0.18020 (12) | −0.17852 (17) | 0.63765 (13) | 0.0402 (3) | |
H3A | 0.2121 | −0.1751 | 0.7152 | 0.048* | |
C4 | 0.15471 (9) | −0.03484 (16) | 0.57623 (12) | 0.0327 (3) | |
C5 | 0.10883 (10) | −0.03991 (17) | 0.45969 (12) | 0.0378 (3) | |
H5A | 0.0938 | 0.0562 | 0.4185 | 0.045* | |
C6 | 0.08566 (11) | −0.18695 (17) | 0.40523 (12) | 0.0373 (3) | |
H6A | 0.0541 | −0.1913 | 0.3277 | 0.045* | |
C7 | 0.36819 (10) | 0.17138 (16) | 0.67652 (12) | 0.0350 (3) | |
C8 | 0.44914 (12) | 0.07699 (19) | 0.72637 (14) | 0.0458 (4) | |
H8A | 0.4469 | 0.0104 | 0.7885 | 0.055* | |
C9 | 0.53378 (13) | 0.0824 (2) | 0.68300 (16) | 0.0534 (4) | |
H9A | 0.5888 | 0.0200 | 0.7174 | 0.064* | |
C10 | 0.53818 (12) | 0.1784 (2) | 0.58966 (15) | 0.0480 (4) | |
C11 | 0.45459 (13) | 0.2703 (2) | 0.53965 (15) | 0.0520 (4) | |
H11A | 0.4559 | 0.3342 | 0.4759 | 0.062* | |
C12 | 0.37032 (11) | 0.2686 (2) | 0.58227 (14) | 0.0459 (4) | |
H12A | 0.3155 | 0.3318 | 0.5485 | 0.055* | |
C13 | 0.63014 (15) | 0.1834 (3) | 0.5431 (2) | 0.0725 (7) | |
H13A | 0.6197 | 0.2557 | 0.4785 | 0.109* | |
H13B | 0.6443 | 0.0764 | 0.5193 | 0.109* | |
H13C | 0.6853 | 0.2213 | 0.6018 | 0.109* | |
O1 | 0.03448 (11) | −0.48393 (16) | 0.31199 (11) | 0.0632 (4) | |
O2 | 0.10269 (10) | −0.60871 (14) | 0.46682 (11) | 0.0581 (3) | |
O3 | 0.23991 (9) | 0.34005 (14) | 0.75585 (11) | 0.0511 (3) | |
O4 | 0.27479 (9) | 0.05744 (14) | 0.82372 (9) | 0.0481 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0394 (2) | 0.0365 (2) | 0.0334 (2) | −0.00241 (12) | 0.00712 (15) | −0.00557 (12) |
N1 | 0.0406 (6) | 0.0372 (6) | 0.0433 (7) | −0.0028 (5) | 0.0104 (5) | −0.0040 (5) |
N2 | 0.0376 (6) | 0.0326 (6) | 0.0442 (7) | 0.0021 (5) | 0.0009 (5) | −0.0015 (5) |
C1 | 0.0317 (6) | 0.0340 (7) | 0.0353 (7) | −0.0013 (5) | 0.0074 (5) | −0.0012 (5) |
C2 | 0.0476 (8) | 0.0328 (7) | 0.0365 (7) | −0.0001 (5) | 0.0036 (6) | 0.0065 (5) |
C3 | 0.0474 (8) | 0.0384 (7) | 0.0301 (7) | −0.0015 (6) | −0.0007 (6) | 0.0029 (5) |
C4 | 0.0288 (6) | 0.0336 (6) | 0.0348 (7) | −0.0014 (5) | 0.0053 (5) | −0.0002 (5) |
C5 | 0.0406 (7) | 0.0343 (7) | 0.0356 (7) | 0.0044 (5) | 0.0030 (5) | 0.0062 (5) |
C6 | 0.0384 (7) | 0.0413 (7) | 0.0293 (7) | 0.0024 (5) | 0.0015 (5) | 0.0019 (5) |
C7 | 0.0371 (7) | 0.0356 (7) | 0.0303 (7) | −0.0001 (5) | 0.0035 (5) | −0.0038 (5) |
C8 | 0.0491 (8) | 0.0444 (8) | 0.0418 (8) | 0.0092 (7) | 0.0063 (6) | 0.0045 (6) |
C9 | 0.0436 (8) | 0.0546 (9) | 0.0591 (10) | 0.0140 (7) | 0.0056 (7) | −0.0032 (8) |
C10 | 0.0412 (8) | 0.0541 (9) | 0.0500 (9) | −0.0069 (6) | 0.0129 (7) | −0.0193 (7) |
C11 | 0.0516 (9) | 0.0640 (10) | 0.0411 (8) | −0.0057 (8) | 0.0119 (7) | 0.0065 (7) |
C12 | 0.0410 (7) | 0.0538 (9) | 0.0405 (8) | 0.0046 (7) | 0.0044 (6) | 0.0094 (7) |
C13 | 0.0526 (11) | 0.0904 (16) | 0.0821 (15) | −0.0167 (10) | 0.0310 (10) | −0.0326 (12) |
O1 | 0.0801 (9) | 0.0537 (7) | 0.0462 (7) | −0.0084 (6) | −0.0048 (6) | −0.0125 (5) |
O2 | 0.0773 (8) | 0.0338 (6) | 0.0617 (8) | −0.0023 (5) | 0.0133 (6) | 0.0024 (5) |
O3 | 0.0550 (7) | 0.0417 (7) | 0.0577 (7) | −0.0005 (5) | 0.0155 (6) | −0.0159 (5) |
O4 | 0.0560 (6) | 0.0548 (7) | 0.0318 (5) | −0.0083 (5) | 0.0066 (4) | 0.0014 (5) |
Geometric parameters (Å, º) top
S1—O4 | 1.4262 (11) | C5—H5A | 0.9300 |
S1—O3 | 1.4298 (12) | C6—H6A | 0.9300 |
S1—N2 | 1.6360 (13) | C7—C8 | 1.378 (2) |
S1—C7 | 1.7597 (15) | C7—C12 | 1.388 (2) |
N1—O1 | 1.2141 (18) | C8—C9 | 1.384 (2) |
N1—O2 | 1.2224 (17) | C8—H8A | 0.9300 |
N1—C1 | 1.4613 (17) | C9—C10 | 1.380 (3) |
N2—C4 | 1.4118 (17) | C9—H9A | 0.9300 |
N2—H2A | 0.8600 | C10—C11 | 1.393 (3) |
C1—C2 | 1.375 (2) | C10—C13 | 1.500 (2) |
C1—C6 | 1.3842 (19) | C11—C12 | 1.373 (2) |
C2—C3 | 1.384 (2) | C11—H11A | 0.9300 |
C2—H2B | 0.9300 | C12—H12A | 0.9300 |
C3—C4 | 1.3938 (19) | C13—H13A | 0.9600 |
C3—H3A | 0.9300 | C13—H13B | 0.9600 |
C4—C5 | 1.392 (2) | C13—H13C | 0.9600 |
C5—C6 | 1.377 (2) | | |
| | | |
O4—S1—O3 | 120.08 (7) | C5—C6—C1 | 118.73 (13) |
O4—S1—N2 | 109.04 (7) | C5—C6—H6A | 120.6 |
O3—S1—N2 | 104.24 (7) | C1—C6—H6A | 120.6 |
O4—S1—C7 | 108.08 (7) | C8—C7—C12 | 120.61 (14) |
O3—S1—C7 | 108.50 (7) | C8—C7—S1 | 120.50 (12) |
N2—S1—C7 | 106.06 (7) | C12—C7—S1 | 118.87 (11) |
O1—N1—O2 | 122.52 (13) | C7—C8—C9 | 119.33 (15) |
O1—N1—C1 | 118.83 (13) | C7—C8—H8A | 120.3 |
O2—N1—C1 | 118.62 (12) | C9—C8—H8A | 120.3 |
C4—N2—S1 | 126.64 (10) | C10—C9—C8 | 121.33 (15) |
C4—N2—H2A | 116.7 | C10—C9—H9A | 119.3 |
S1—N2—H2A | 116.7 | C8—C9—H9A | 119.3 |
C2—C1—C6 | 122.18 (13) | C9—C10—C11 | 118.11 (15) |
C2—C1—N1 | 119.27 (12) | C9—C10—C13 | 120.99 (18) |
C6—C1—N1 | 118.51 (13) | C11—C10—C13 | 120.90 (18) |
C1—C2—C3 | 119.07 (13) | C12—C11—C10 | 121.56 (16) |
C1—C2—H2B | 120.5 | C12—C11—H11A | 119.2 |
C3—C2—H2B | 120.5 | C10—C11—H11A | 119.2 |
C2—C3—C4 | 119.63 (14) | C11—C12—C7 | 119.04 (15) |
C2—C3—H3A | 120.2 | C11—C12—H12A | 120.5 |
C4—C3—H3A | 120.2 | C7—C12—H12A | 120.5 |
C5—C4—C3 | 120.21 (13) | C10—C13—H13A | 109.5 |
C5—C4—N2 | 117.44 (12) | C10—C13—H13B | 109.5 |
C3—C4—N2 | 122.25 (13) | H13A—C13—H13B | 109.5 |
C6—C5—C4 | 120.15 (13) | C10—C13—H13C | 109.5 |
C6—C5—H5A | 119.9 | H13A—C13—H13C | 109.5 |
C4—C5—H5A | 119.9 | H13B—C13—H13C | 109.5 |
| | | |
O4—S1—N2—C4 | −50.32 (14) | N1—C1—C6—C5 | 177.02 (12) |
O3—S1—N2—C4 | −179.71 (12) | O4—S1—C7—C8 | −5.81 (14) |
C7—S1—N2—C4 | 65.85 (13) | O3—S1—C7—C8 | 125.89 (13) |
O1—N1—C1—C2 | 176.11 (15) | N2—S1—C7—C8 | −122.62 (13) |
O2—N1—C1—C2 | −2.2 (2) | O4—S1—C7—C12 | 175.94 (12) |
O1—N1—C1—C6 | −1.6 (2) | O3—S1—C7—C12 | −52.36 (14) |
O2—N1—C1—C6 | −179.93 (13) | N2—S1—C7—C12 | 59.12 (13) |
C6—C1—C2—C3 | 1.3 (2) | C12—C7—C8—C9 | 1.3 (2) |
N1—C1—C2—C3 | −176.35 (13) | S1—C7—C8—C9 | −176.93 (12) |
C1—C2—C3—C4 | −0.3 (2) | C7—C8—C9—C10 | −1.1 (3) |
C2—C3—C4—C5 | −1.3 (2) | C8—C9—C10—C11 | −0.1 (3) |
C2—C3—C4—N2 | 175.09 (14) | C8—C9—C10—C13 | −179.94 (16) |
S1—N2—C4—C5 | −146.39 (12) | C9—C10—C11—C12 | 1.1 (3) |
S1—N2—C4—C3 | 37.13 (19) | C13—C10—C11—C12 | −179.10 (17) |
C3—C4—C5—C6 | 2.0 (2) | C10—C11—C12—C7 | −0.8 (3) |
N2—C4—C5—C6 | −174.60 (13) | C8—C7—C12—C11 | −0.4 (2) |
C4—C5—C6—C1 | −1.0 (2) | S1—C7—C12—C11 | 177.89 (13) |
C2—C1—C6—C5 | −0.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.30 | 2.9672 (18) | 135 |
Symmetry code: (i) x, y+1, z. |