organic compounds
N-(3,5-Dimethylphenyl)-4-nitrobenzenesulfonamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
There are two independent molecules in the 14H14N2O4S, in which the dihedral angles between the benzene rings are 56.22 (15) and 58.16 (14)°. In the crystal, N—H⋯Onitro hydrogen bonds link the molecules into zigzag chains running along the a-axis direction.
of the title compound, CRelated literature
For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012) and of N-chloroarylsulfonamides, see: Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond & Grant (2001).
Experimental
Crystal data
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812047502/bt6865sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047502/bt6865Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047502/bt6865Isup3.cml
The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with 3,5-dimethylaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid, N-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.
Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.
H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å, methyl C—H = 0.96 Å. The amino H atoms were freely refined with the N—H distance restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq(C-aromatic, N) or 1.5 Ueq(C-methyl).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008.C14H14N2O4S | F(000) = 1280 |
Mr = 306.33 | Dx = 1.408 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1548 reflections |
a = 14.708 (1) Å | θ = 2.6–27.9° |
b = 7.9410 (7) Å | µ = 0.24 mm−1 |
c = 24.741 (2) Å | T = 293 K |
V = 2889.7 (4) Å3 | Prism, colourless |
Z = 8 | 0.38 × 0.30 × 0.24 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 3714 independent reflections |
Radiation source: fine-focus sealed tube | 2624 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Rotation method data acquisition using ω scans | θmax = 25.4°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −17→6 |
Tmin = 0.914, Tmax = 0.944 | k = −9→7 |
6693 measured reflections | l = −16→29 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0295P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.18 e Å−3 |
3714 reflections | Δρmin = −0.18 e Å−3 |
390 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0037 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1005 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.04 (8) |
C14H14N2O4S | V = 2889.7 (4) Å3 |
Mr = 306.33 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.708 (1) Å | µ = 0.24 mm−1 |
b = 7.9410 (7) Å | T = 293 K |
c = 24.741 (2) Å | 0.38 × 0.30 × 0.24 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 3714 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2624 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.944 | Rint = 0.030 |
6693 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | Δρmax = 0.18 e Å−3 |
S = 1.00 | Δρmin = −0.18 e Å−3 |
3714 reflections | Absolute structure: Flack (1983), 1005 Friedel pairs |
390 parameters | Absolute structure parameter: 0.04 (8) |
3 restraints |
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.20029 (7) | 0.68335 (15) | 0.47849 (4) | 0.0495 (3) | |
O1 | 0.2499 (2) | 0.8380 (4) | 0.48316 (13) | 0.0631 (9) | |
O2 | 0.1473 (2) | 0.6216 (4) | 0.52234 (12) | 0.0710 (10) | |
O3 | 0.4490 (3) | 0.0058 (6) | 0.42894 (19) | 0.1052 (15) | |
O4 | 0.5359 (3) | 0.1925 (6) | 0.3950 (2) | 0.1156 (17) | |
N1 | 0.1295 (2) | 0.7027 (5) | 0.42794 (16) | 0.0476 (9) | |
H1N | 0.094 (2) | 0.618 (3) | 0.4263 (16) | 0.057* | |
N2 | 0.4666 (3) | 0.1511 (6) | 0.41830 (18) | 0.0681 (13) | |
C1 | 0.2802 (2) | 0.5258 (5) | 0.46126 (14) | 0.0381 (9) | |
C2 | 0.2595 (3) | 0.3583 (5) | 0.47151 (17) | 0.0517 (11) | |
H2 | 0.2046 | 0.3295 | 0.4877 | 0.062* | |
C3 | 0.3211 (3) | 0.2352 (5) | 0.4575 (2) | 0.0550 (16) | |
H3 | 0.3089 | 0.1223 | 0.4643 | 0.066* | |
C4 | 0.4008 (3) | 0.2829 (6) | 0.43324 (19) | 0.0481 (12) | |
C5 | 0.4228 (3) | 0.4459 (6) | 0.42402 (17) | 0.0541 (12) | |
H5 | 0.4784 | 0.4739 | 0.4085 | 0.065* | |
C6 | 0.3614 (3) | 0.5702 (5) | 0.43812 (16) | 0.0483 (11) | |
H6 | 0.3751 | 0.6829 | 0.4320 | 0.058* | |
C7 | 0.1582 (3) | 0.7666 (5) | 0.3761 (2) | 0.0422 (12) | |
C8 | 0.1593 (3) | 0.6614 (6) | 0.33197 (19) | 0.0492 (11) | |
H8 | 0.1446 | 0.5483 | 0.3364 | 0.059* | |
C9 | 0.1817 (3) | 0.7198 (7) | 0.2813 (2) | 0.0553 (14) | |
C10 | 0.2049 (3) | 0.8896 (7) | 0.2769 (2) | 0.0626 (13) | |
H10 | 0.2208 | 0.9325 | 0.2432 | 0.075* | |
C11 | 0.2050 (3) | 0.9959 (6) | 0.3212 (2) | 0.0601 (13) | |
C12 | 0.1793 (3) | 0.9334 (5) | 0.37078 (18) | 0.0504 (11) | |
H12 | 0.1763 | 1.0045 | 0.4006 | 0.060* | |
C13 | 0.1821 (3) | 0.6099 (7) | 0.2319 (2) | 0.0839 (17) | |
H13A | 0.1218 | 0.6037 | 0.2173 | 0.126* | |
H13B | 0.2024 | 0.4989 | 0.2415 | 0.126* | |
H13C | 0.2225 | 0.6568 | 0.2054 | 0.126* | |
C14 | 0.2293 (4) | 1.1823 (6) | 0.3147 (3) | 0.103 (2) | |
H14A | 0.2189 | 1.2162 | 0.2779 | 0.155* | |
H14B | 0.2921 | 1.1990 | 0.3237 | 0.155* | |
H14C | 0.1920 | 1.2487 | 0.3384 | 0.155* | |
S2 | −0.03497 (7) | 0.80910 (15) | 0.05640 (5) | 0.0475 (3) | |
O5 | 0.01620 (19) | 0.6581 (3) | 0.05262 (13) | 0.0618 (8) | |
O6 | −0.0860 (2) | 0.8702 (4) | 0.01140 (12) | 0.0664 (9) | |
O7 | 0.2958 (3) | 1.3138 (6) | 0.1386 (2) | 0.1138 (18) | |
O8 | 0.2121 (3) | 1.4949 (5) | 0.09994 (16) | 0.0838 (11) | |
N3 | −0.1086 (2) | 0.7845 (4) | 0.10462 (16) | 0.0446 (10) | |
H3N | −0.142 (2) | 0.871 (3) | 0.1028 (15) | 0.054* | |
N4 | 0.2285 (3) | 1.3523 (6) | 0.11394 (18) | 0.0665 (12) | |
C15 | 0.0414 (2) | 0.9711 (5) | 0.07551 (14) | 0.0387 (10) | |
C16 | 0.1215 (3) | 0.9299 (5) | 0.10135 (17) | 0.0530 (11) | |
H16 | 0.1338 | 0.8183 | 0.1101 | 0.064* | |
C17 | 0.1833 (3) | 1.0543 (6) | 0.1142 (2) | 0.0571 (13) | |
H17 | 0.2379 | 1.0285 | 0.1313 | 0.069* | |
C18 | 0.1616 (3) | 1.2180 (6) | 0.1009 (2) | 0.0440 (12) | |
C19 | 0.0830 (3) | 1.2609 (5) | 0.0751 (2) | 0.0486 (14) | |
H19 | 0.0707 | 1.3723 | 0.0661 | 0.058* | |
C20 | 0.0221 (2) | 1.1340 (5) | 0.06260 (17) | 0.0478 (11) | |
H20 | −0.0323 | 1.1600 | 0.0453 | 0.057* | |
C21 | −0.0857 (3) | 0.7124 (5) | 0.1559 (2) | 0.0389 (11) | |
C22 | −0.0684 (3) | 0.5420 (5) | 0.16021 (18) | 0.0468 (11) | |
H22 | −0.0689 | 0.4750 | 0.1294 | 0.056* | |
C23 | −0.0504 (2) | 0.4699 (5) | 0.2103 (2) | 0.0481 (11) | |
C24 | −0.0518 (3) | 0.5743 (6) | 0.2550 (2) | 0.0538 (12) | |
H24 | −0.0418 | 0.5267 | 0.2889 | 0.065* | |
C25 | −0.0673 (3) | 0.7446 (5) | 0.2521 (2) | 0.0483 (14) | |
C26 | −0.0837 (3) | 0.8133 (6) | 0.2017 (2) | 0.0505 (11) | |
H26 | −0.0935 | 0.9285 | 0.1984 | 0.061* | |
C27 | −0.0307 (4) | 0.2842 (5) | 0.2156 (2) | 0.0811 (17) | |
H27A | −0.0110 | 0.2407 | 0.1814 | 0.122* | |
H27B | −0.0849 | 0.2264 | 0.2268 | 0.122* | |
H27C | 0.0162 | 0.2674 | 0.2421 | 0.122* | |
C28 | −0.0679 (3) | 0.8542 (7) | 0.30165 (19) | 0.0821 (16) | |
H28A | −0.0105 | 0.9109 | 0.3048 | 0.123* | |
H28B | −0.0778 | 0.7856 | 0.3331 | 0.123* | |
H28C | −0.1157 | 0.9359 | 0.2987 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0542 (6) | 0.0496 (8) | 0.0446 (7) | 0.0110 (6) | 0.0033 (6) | −0.0041 (7) |
O1 | 0.074 (2) | 0.0460 (19) | 0.069 (2) | 0.0071 (18) | −0.0228 (18) | −0.0130 (19) |
O2 | 0.077 (2) | 0.086 (2) | 0.0502 (19) | 0.0283 (19) | 0.0294 (17) | 0.0126 (18) |
O3 | 0.102 (3) | 0.062 (2) | 0.151 (4) | 0.034 (3) | 0.006 (3) | −0.027 (3) |
O4 | 0.077 (3) | 0.117 (3) | 0.153 (5) | 0.029 (3) | 0.042 (3) | −0.034 (3) |
N1 | 0.037 (2) | 0.046 (2) | 0.060 (3) | −0.0075 (18) | 0.0004 (18) | 0.003 (2) |
N2 | 0.065 (3) | 0.067 (3) | 0.072 (3) | 0.019 (3) | −0.007 (2) | −0.022 (3) |
C1 | 0.042 (2) | 0.036 (2) | 0.036 (2) | 0.003 (2) | 0.0014 (18) | 0.0015 (19) |
C2 | 0.044 (2) | 0.047 (3) | 0.064 (3) | 0.000 (2) | 0.005 (2) | 0.005 (2) |
C3 | 0.054 (3) | 0.034 (3) | 0.078 (5) | 0.002 (2) | −0.008 (3) | 0.000 (2) |
C4 | 0.047 (3) | 0.052 (3) | 0.046 (3) | 0.018 (3) | 0.000 (2) | −0.011 (2) |
C5 | 0.049 (3) | 0.059 (3) | 0.054 (3) | −0.003 (3) | 0.010 (2) | 0.007 (3) |
C6 | 0.054 (3) | 0.041 (3) | 0.050 (3) | −0.004 (2) | 0.004 (2) | 0.008 (2) |
C7 | 0.033 (2) | 0.044 (3) | 0.050 (3) | 0.006 (2) | −0.001 (2) | 0.002 (2) |
C8 | 0.040 (2) | 0.048 (3) | 0.059 (3) | −0.001 (2) | −0.001 (2) | −0.002 (3) |
C9 | 0.050 (3) | 0.065 (3) | 0.051 (4) | −0.001 (3) | −0.002 (3) | −0.006 (3) |
C10 | 0.066 (3) | 0.072 (4) | 0.050 (3) | −0.001 (3) | 0.004 (2) | 0.012 (3) |
C11 | 0.066 (3) | 0.051 (3) | 0.063 (3) | 0.000 (2) | −0.005 (3) | 0.013 (3) |
C12 | 0.054 (3) | 0.044 (3) | 0.053 (3) | 0.000 (2) | −0.009 (2) | −0.008 (2) |
C13 | 0.076 (3) | 0.107 (4) | 0.069 (4) | −0.007 (3) | 0.011 (3) | −0.026 (3) |
C14 | 0.145 (5) | 0.058 (3) | 0.107 (5) | −0.010 (4) | 0.005 (4) | 0.026 (4) |
S2 | 0.0512 (6) | 0.0443 (7) | 0.0471 (7) | −0.0100 (6) | 0.0015 (6) | −0.0028 (7) |
O5 | 0.070 (2) | 0.0401 (17) | 0.075 (2) | −0.0035 (16) | 0.0198 (18) | −0.0141 (18) |
O6 | 0.073 (2) | 0.078 (2) | 0.0489 (19) | −0.0261 (18) | −0.0172 (16) | 0.0081 (18) |
O7 | 0.074 (3) | 0.095 (3) | 0.173 (5) | −0.004 (3) | −0.053 (3) | −0.046 (3) |
O8 | 0.099 (3) | 0.058 (2) | 0.094 (3) | −0.029 (2) | 0.007 (2) | −0.014 (2) |
N3 | 0.039 (2) | 0.041 (2) | 0.054 (3) | 0.0005 (17) | 0.0038 (18) | 0.003 (2) |
N4 | 0.057 (3) | 0.070 (3) | 0.073 (3) | −0.013 (3) | 0.005 (2) | −0.036 (3) |
C15 | 0.038 (2) | 0.036 (2) | 0.042 (2) | 0.002 (2) | −0.0009 (19) | −0.0019 (19) |
C16 | 0.056 (3) | 0.047 (3) | 0.056 (3) | 0.006 (2) | −0.008 (2) | 0.009 (2) |
C17 | 0.042 (3) | 0.063 (3) | 0.066 (3) | −0.003 (3) | −0.018 (2) | −0.011 (3) |
C18 | 0.036 (2) | 0.043 (3) | 0.053 (3) | −0.004 (2) | 0.005 (2) | −0.019 (2) |
C19 | 0.051 (3) | 0.036 (3) | 0.059 (4) | 0.005 (2) | 0.004 (2) | −0.004 (2) |
C20 | 0.039 (2) | 0.044 (2) | 0.061 (3) | 0.005 (2) | −0.009 (2) | −0.002 (2) |
C21 | 0.032 (2) | 0.040 (3) | 0.045 (3) | −0.002 (2) | 0.0048 (19) | −0.003 (3) |
C22 | 0.046 (2) | 0.037 (3) | 0.057 (3) | −0.006 (2) | 0.003 (2) | −0.008 (2) |
C23 | 0.052 (3) | 0.031 (2) | 0.062 (3) | −0.005 (2) | −0.001 (2) | 0.003 (2) |
C24 | 0.049 (3) | 0.064 (3) | 0.048 (3) | −0.005 (2) | −0.002 (2) | 0.011 (3) |
C25 | 0.044 (3) | 0.049 (3) | 0.051 (4) | 0.001 (2) | −0.003 (3) | −0.009 (2) |
C26 | 0.042 (2) | 0.039 (3) | 0.070 (4) | −0.004 (2) | 0.004 (2) | −0.008 (3) |
C27 | 0.108 (4) | 0.051 (3) | 0.084 (4) | 0.006 (3) | −0.017 (3) | 0.007 (3) |
C28 | 0.086 (4) | 0.101 (4) | 0.059 (4) | 0.017 (3) | −0.001 (3) | −0.029 (3) |
S1—O2 | 1.423 (3) | S2—O5 | 1.419 (3) |
S1—O1 | 1.433 (3) | S2—O6 | 1.428 (3) |
S1—N1 | 1.634 (4) | S2—N3 | 1.623 (4) |
S1—C1 | 1.769 (4) | S2—C15 | 1.772 (4) |
O3—N2 | 1.211 (5) | O7—N4 | 1.203 (5) |
O4—N2 | 1.216 (5) | O8—N4 | 1.208 (5) |
N1—C7 | 1.442 (6) | N3—C21 | 1.433 (6) |
N1—H1N | 0.849 (18) | N3—H3N | 0.843 (18) |
N2—C4 | 1.473 (6) | N4—C18 | 1.486 (6) |
C1—C6 | 1.371 (5) | C15—C20 | 1.363 (5) |
C1—C2 | 1.388 (5) | C15—C16 | 1.379 (5) |
C2—C3 | 1.378 (6) | C16—C17 | 1.380 (6) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.369 (7) | C17—C18 | 1.378 (6) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.354 (5) | C18—C19 | 1.364 (6) |
C5—C6 | 1.382 (5) | C19—C20 | 1.383 (5) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C12 | 1.366 (5) | C21—C22 | 1.380 (5) |
C7—C8 | 1.376 (6) | C21—C26 | 1.387 (6) |
C8—C9 | 1.376 (7) | C22—C23 | 1.391 (5) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.395 (6) | C23—C24 | 1.382 (6) |
C9—C13 | 1.502 (7) | C23—C27 | 1.509 (5) |
C10—C11 | 1.383 (6) | C24—C25 | 1.373 (5) |
C10—H10 | 0.9300 | C24—H24 | 0.9300 |
C11—C12 | 1.376 (6) | C25—C26 | 1.382 (7) |
C11—C14 | 1.532 (6) | C25—C28 | 1.504 (7) |
C12—H12 | 0.9300 | C26—H26 | 0.9300 |
C13—H13A | 0.9600 | C27—H27A | 0.9600 |
C13—H13B | 0.9600 | C27—H27B | 0.9600 |
C13—H13C | 0.9600 | C27—H27C | 0.9600 |
C14—H14A | 0.9600 | C28—H28A | 0.9600 |
C14—H14B | 0.9600 | C28—H28B | 0.9600 |
C14—H14C | 0.9600 | C28—H28C | 0.9600 |
O2—S1—O1 | 120.9 (2) | O5—S2—O6 | 121.0 (2) |
O2—S1—N1 | 105.49 (19) | O5—S2—N3 | 107.50 (19) |
O1—S1—N1 | 107.79 (19) | O6—S2—N3 | 105.3 (2) |
O2—S1—C1 | 107.69 (18) | O5—S2—C15 | 107.14 (17) |
O1—S1—C1 | 106.67 (18) | O6—S2—C15 | 107.14 (17) |
N1—S1—C1 | 107.78 (19) | N3—S2—C15 | 108.30 (19) |
C7—N1—S1 | 121.8 (3) | C21—N3—S2 | 122.8 (3) |
C7—N1—H1N | 115 (3) | C21—N3—H3N | 121 (3) |
S1—N1—H1N | 110 (3) | S2—N3—H3N | 104 (3) |
O3—N2—O4 | 122.6 (5) | O7—N4—O8 | 123.2 (5) |
O3—N2—C4 | 118.8 (5) | O7—N4—C18 | 118.2 (5) |
O4—N2—C4 | 118.6 (5) | O8—N4—C18 | 118.6 (5) |
C6—C1—C2 | 120.9 (4) | C20—C15—C16 | 120.8 (4) |
C6—C1—S1 | 119.9 (3) | C20—C15—S2 | 119.6 (3) |
C2—C1—S1 | 119.2 (3) | C16—C15—S2 | 119.5 (3) |
C3—C2—C1 | 119.3 (4) | C15—C16—C17 | 119.9 (4) |
C3—C2—H2 | 120.3 | C15—C16—H16 | 120.0 |
C1—C2—H2 | 120.3 | C17—C16—H16 | 120.0 |
C4—C3—C2 | 118.5 (4) | C18—C17—C16 | 117.9 (4) |
C4—C3—H3 | 120.8 | C18—C17—H17 | 121.0 |
C2—C3—H3 | 120.8 | C16—C17—H17 | 121.0 |
C5—C4—C3 | 122.9 (4) | C19—C18—C17 | 122.9 (4) |
C5—C4—N2 | 118.6 (4) | C19—C18—N4 | 118.9 (4) |
C3—C4—N2 | 118.4 (5) | C17—C18—N4 | 118.2 (4) |
C4—C5—C6 | 118.9 (4) | C18—C19—C20 | 118.2 (4) |
C4—C5—H5 | 120.5 | C18—C19—H19 | 120.9 |
C6—C5—H5 | 120.5 | C20—C19—H19 | 120.9 |
C1—C6—C5 | 119.4 (4) | C15—C20—C19 | 120.2 (4) |
C1—C6—H6 | 120.3 | C15—C20—H20 | 119.9 |
C5—C6—H6 | 120.3 | C19—C20—H20 | 119.9 |
C12—C7—C8 | 120.6 (5) | C22—C21—C26 | 120.0 (5) |
C12—C7—N1 | 119.6 (5) | C22—C21—N3 | 120.2 (4) |
C8—C7—N1 | 119.7 (4) | C26—C21—N3 | 119.8 (4) |
C7—C8—C9 | 121.4 (5) | C21—C22—C23 | 120.5 (4) |
C7—C8—H8 | 119.3 | C21—C22—H22 | 119.8 |
C9—C8—H8 | 119.3 | C23—C22—H22 | 119.8 |
C8—C9—C10 | 117.1 (5) | C24—C23—C22 | 117.6 (4) |
C8—C9—C13 | 123.1 (5) | C24—C23—C27 | 121.3 (5) |
C10—C9—C13 | 119.8 (5) | C22—C23—C27 | 121.1 (4) |
C11—C10—C9 | 121.9 (5) | C25—C24—C23 | 123.4 (5) |
C11—C10—H10 | 119.0 | C25—C24—H24 | 118.3 |
C9—C10—H10 | 119.0 | C23—C24—H24 | 118.3 |
C12—C11—C10 | 119.1 (4) | C24—C25—C26 | 117.8 (5) |
C12—C11—C14 | 120.4 (5) | C24—C25—C28 | 121.8 (5) |
C10—C11—C14 | 120.5 (5) | C26—C25—C28 | 120.4 (4) |
C7—C12—C11 | 119.9 (5) | C25—C26—C21 | 120.8 (4) |
C7—C12—H12 | 120.1 | C25—C26—H26 | 119.6 |
C11—C12—H12 | 120.1 | C21—C26—H26 | 119.6 |
C9—C13—H13A | 109.5 | C23—C27—H27A | 109.5 |
C9—C13—H13B | 109.5 | C23—C27—H27B | 109.5 |
H13A—C13—H13B | 109.5 | H27A—C27—H27B | 109.5 |
C9—C13—H13C | 109.5 | C23—C27—H27C | 109.5 |
H13A—C13—H13C | 109.5 | H27A—C27—H27C | 109.5 |
H13B—C13—H13C | 109.5 | H27B—C27—H27C | 109.5 |
C11—C14—H14A | 109.5 | C25—C28—H28A | 109.5 |
C11—C14—H14B | 109.5 | C25—C28—H28B | 109.5 |
H14A—C14—H14B | 109.5 | H28A—C28—H28B | 109.5 |
C11—C14—H14C | 109.5 | C25—C28—H28C | 109.5 |
H14A—C14—H14C | 109.5 | H28A—C28—H28C | 109.5 |
H14B—C14—H14C | 109.5 | H28B—C28—H28C | 109.5 |
O2—S1—N1—C7 | 178.5 (3) | O5—S2—N3—C21 | 44.9 (4) |
O1—S1—N1—C7 | 48.1 (4) | O6—S2—N3—C21 | 175.1 (3) |
C1—S1—N1—C7 | −66.7 (4) | C15—S2—N3—C21 | −70.6 (4) |
O2—S1—C1—C6 | −152.5 (3) | O5—S2—C15—C20 | 154.9 (3) |
O1—S1—C1—C6 | −21.4 (4) | O6—S2—C15—C20 | 23.6 (4) |
N1—S1—C1—C6 | 94.1 (3) | N3—S2—C15—C20 | −89.4 (3) |
O2—S1—C1—C2 | 27.4 (4) | O5—S2—C15—C16 | −22.5 (4) |
O1—S1—C1—C2 | 158.5 (3) | O6—S2—C15—C16 | −153.7 (3) |
N1—S1—C1—C2 | −85.9 (3) | N3—S2—C15—C16 | 93.2 (3) |
C6—C1—C2—C3 | −0.9 (6) | C20—C15—C16—C17 | −0.3 (6) |
S1—C1—C2—C3 | 179.2 (3) | S2—C15—C16—C17 | 177.1 (3) |
C1—C2—C3—C4 | −0.7 (7) | C15—C16—C17—C18 | 0.7 (7) |
C2—C3—C4—C5 | 2.2 (7) | C16—C17—C18—C19 | −1.1 (7) |
C2—C3—C4—N2 | 180.0 (4) | C16—C17—C18—N4 | −179.1 (4) |
O3—N2—C4—C5 | 176.4 (5) | O7—N4—C18—C19 | 177.1 (5) |
O4—N2—C4—C5 | −4.7 (7) | O8—N4—C18—C19 | −1.9 (6) |
O3—N2—C4—C3 | −1.5 (7) | O7—N4—C18—C17 | −4.9 (7) |
O4—N2—C4—C3 | 177.4 (5) | O8—N4—C18—C17 | 176.2 (5) |
C3—C4—C5—C6 | −2.0 (7) | C17—C18—C19—C20 | 1.1 (7) |
N2—C4—C5—C6 | −179.8 (4) | N4—C18—C19—C20 | 179.1 (4) |
C2—C1—C6—C5 | 1.1 (6) | C16—C15—C20—C19 | 0.3 (6) |
S1—C1—C6—C5 | −179.0 (3) | S2—C15—C20—C19 | −177.1 (3) |
C4—C5—C6—C1 | 0.3 (6) | C18—C19—C20—C15 | −0.7 (6) |
S1—N1—C7—C12 | −71.1 (5) | S2—N3—C21—C22 | −72.3 (5) |
S1—N1—C7—C8 | 112.5 (4) | S2—N3—C21—C26 | 109.8 (4) |
C12—C7—C8—C9 | 0.2 (6) | C26—C21—C22—C23 | 1.0 (6) |
N1—C7—C8—C9 | 176.6 (4) | N3—C21—C22—C23 | −176.9 (3) |
C7—C8—C9—C10 | 1.2 (6) | C21—C22—C23—C24 | 0.9 (5) |
C7—C8—C9—C13 | −178.9 (4) | C21—C22—C23—C27 | −179.5 (4) |
C8—C9—C10—C11 | −0.4 (7) | C22—C23—C24—C25 | −2.0 (6) |
C13—C9—C10—C11 | 179.6 (4) | C27—C23—C24—C25 | 178.4 (4) |
C9—C10—C11—C12 | −1.6 (7) | C23—C24—C25—C26 | 1.1 (7) |
C9—C10—C11—C14 | −179.0 (5) | C23—C24—C25—C28 | −179.7 (4) |
C8—C7—C12—C11 | −2.3 (6) | C24—C25—C26—C21 | 0.9 (6) |
N1—C7—C12—C11 | −178.7 (3) | C28—C25—C26—C21 | −178.3 (4) |
C10—C11—C12—C7 | 3.0 (6) | C22—C21—C26—C25 | −1.9 (6) |
C14—C11—C12—C7 | −179.7 (4) | N3—C21—C26—C25 | 176.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.85 (2) | 2.35 (2) | 3.129 (5) | 152 (3) |
N3—H3N···O8ii | 0.84 (2) | 2.40 (2) | 3.168 (5) | 152 (3) |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x−1/2, −y+5/2, z. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O4S |
Mr | 306.33 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 14.708 (1), 7.9410 (7), 24.741 (2) |
V (Å3) | 2889.7 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.38 × 0.30 × 0.24 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.914, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6693, 3714, 2624 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.074, 1.00 |
No. of reflections | 3714 |
No. of parameters | 390 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Absolute structure | Flack (1983), 1005 Friedel pairs |
Absolute structure parameter | 0.04 (8) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.849 (18) | 2.35 (2) | 3.129 (5) | 152 (3) |
N3—H3N···O8ii | 0.843 (18) | 2.40 (2) | 3.168 (5) | 152 (3) |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x−1/2, −y+5/2, z. |
Acknowledgements
UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda & Weiss, 1994; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012) and N-chloroarylsulfonamides (Shetty & Gowda, 2004),in the present work, the crystal structure of N-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide (I) has been determined (Fig. 1).
The asymmetric unit of the structure of (I) contains two crystallographically independent molecules, similar to that observed in N-(3,5-dimethylphenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012). The molecules are twisted at the S—N bonds with the torsional angles of -66.67 (38) and -70.56 (39)°, compared to the values of 44.24 (26) and -49.34 (25)° in (II).
The dihedral angles between the sulfonyl and the anilino rings in the two molecules are 56.22 (15)° and 58.16 (14)°, compared to the values of 71.53 (7)° and 72.11 (7)° in (II).
The amide H-atom showed bifurcated intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring, generating S(7) motifs and the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating C(4) motifs (Adsmond et al., 2001).
In the crystal, the intermolecular N–H···O (N) hydrogen bonds (Table 1) link the molecules into zigzag chains running along the a axis. Part of the crystal structure is shown in Fig. 2.