organic compounds
N-(3,5-Dimethylphenyl)-2-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
The 14H14N2O4S, consists of two crystallographically independent molecules. The molecules are twisted at the S—N bonds with C—S—N—C torsion angles of 44.2 (3) and −49.3 (3)°. The dihedral angles between the benzene rings in the two molecules are 71.53 (7) and 72.11 (7)°. The amide H atoms exhibit bifurcated intra- and intermolecular hydrogen bonds; the intramolecular N—H⋯O(N) hydrogen bonds generate S(7) motifs. In the crystal, the independent molecules are separately connected through the intermolecular N—H⋯O(S) hydrogen bonds, generating a C(4) motif and a helical chain along the b axis for one molecule and an R22(8) motif and an inversion dimer for the other. The crystal studied was a pseudo-merohedral twin with (-100/0-10/001), the refined ratio of the twin domains being 0.7876 (12):0.2124 (12).
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 et al. (2001),
Experimental
Crystal data
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Refinement
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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
https://doi.org/10.1107/S1600536812036926/is5184sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036926/is5184Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812036926/is5184Isup3.cml
The title compound was prepared by treating 2-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)-2-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 brown single crystals of the title compound suitable for X-ray diffraction studies were grown in an 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 and the methyl C—H = 0.96 Å. The positions of amino H atoms were refined with the N—H distance restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2Ueq(C-aromatic, N) and 1.5Ueq (C-methyl). Rigid-bond restraints (DELU) were applied for atom paris of C18/C19, N2/C2, O3/N2 and N4/C16. The crystal was refined with the
(-1 0 0/0 -1 0/0 0 1).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
of N-(3,5-dimethylphenyl)-2-nitrobenzenesulfonamide has been determined.The ═O bonds, similar to that observed in N-(3-methylphenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). Further, the conformation of the N—H bond in the —SO2—NH— segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The molecules are twisted at the S—N bonds with C1—S1—N1—C7 and C15—S2—N3—C21 torsion angles of 44.2 (3) and -49.3 (3)°, respectively, compared to the value of 46.97 (16)° in (I). The dihedral angles between the sulfonyl and the anilino rings in the two molecules are 71.53 (7) and 72.11 (7)°, compared to the value of 73.64 (7)° in (I). In each molecule the amide H atom shows an intramolecular hydrogen bond (N1—H1N···O1 and N3—H3N···O7; Table 1) with the O atom of the ortho-nitro group in the sulfonyl benzene ring, generating an S(7) motif (Adsmond et al., 2001). In the crystal, the amide H atoms show intermolecular hydrogen bonds with the sulfonyl oxygen atoms of the other molecule; the N1—H1N···O1i hydrogen bond (symmetry code in Table 1) generates a C(4) motif and a helical chain along the b axis, while the N3—H3N···O6ii hydrogen bond (symmetry code in Table 1) an R22(8) motif and an inversion dimer. A part of the is shown in Fig. 2.
of the title compound consists of two crystallographically independent molecules (Fig. 1). The conformation of the N—C bond in the —SO2—NH—C segment has gauche torsions with respect to the SFor 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 et al. (2001),
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 = 1.402 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2953 reflections |
a = 16.561 (1) Å | θ = 2.5–27.9° |
b = 8.1611 (6) Å | µ = 0.24 mm−1 |
c = 21.476 (2) Å | T = 293 K |
β = 90.056 (7)° | Prism, brown |
V = 2902.6 (4) Å3 | 0.48 × 0.40 × 0.20 mm |
Z = 8 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 5929 independent reflections |
Radiation source: fine-focus sealed tube | 4004 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −20→20 |
Tmin = 0.894, Tmax = 0.954 | k = −10→5 |
12941 measured reflections | l = −19→26 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0703P)2] where P = (Fo2 + 2Fc2)/3 |
5929 reflections | (Δ/σ)max = 0.006 |
390 parameters | Δρmax = 0.32 e Å−3 |
6 restraints | Δρmin = −0.29 e Å−3 |
C14H14N2O4S | V = 2902.6 (4) Å3 |
Mr = 306.33 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.561 (1) Å | µ = 0.24 mm−1 |
b = 8.1611 (6) Å | T = 293 K |
c = 21.476 (2) Å | 0.48 × 0.40 × 0.20 mm |
β = 90.056 (7)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 5929 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 4004 reflections with I > 2σ(I) |
Tmin = 0.894, Tmax = 0.954 | Rint = 0.030 |
12941 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 6 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.32 e Å−3 |
5929 reflections | Δρmin = −0.29 e Å−3 |
390 parameters |
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 | 0.10145 (4) | 0.28567 (9) | 0.27572 (3) | 0.0436 (2) | |
O1 | 0.09244 (13) | 0.4509 (3) | 0.25622 (10) | 0.0612 (6) | |
O2 | 0.13065 (14) | 0.1683 (3) | 0.23195 (10) | 0.0648 (6) | |
O3 | 0.11511 (16) | −0.0493 (3) | 0.33802 (14) | 0.0830 (8) | |
O4 | 0.23948 (19) | −0.1115 (4) | 0.34483 (18) | 0.1090 (11) | |
N1 | 0.01449 (14) | 0.2232 (3) | 0.30039 (11) | 0.0451 (6) | |
H1N | 0.0052 (18) | 0.127 (2) | 0.2925 (14) | 0.054* | |
N2 | 0.18483 (18) | −0.0130 (3) | 0.34824 (13) | 0.0597 (7) | |
C1 | 0.16894 (15) | 0.2911 (3) | 0.34040 (13) | 0.0390 (6) | |
C2 | 0.20431 (17) | 0.1548 (4) | 0.36690 (13) | 0.0459 (7) | |
C3 | 0.26122 (18) | 0.1709 (5) | 0.41434 (16) | 0.0614 (9) | |
H3 | 0.2854 | 0.0785 | 0.4315 | 0.074* | |
C4 | 0.2813 (2) | 0.3250 (6) | 0.43555 (16) | 0.0657 (10) | |
H4 | 0.3182 | 0.3364 | 0.4680 | 0.079* | |
C5 | 0.24775 (18) | 0.4600 (5) | 0.40949 (17) | 0.0634 (10) | |
H5 | 0.2625 | 0.5635 | 0.4236 | 0.076* | |
C6 | 0.19187 (17) | 0.4449 (4) | 0.36223 (14) | 0.0513 (8) | |
H6 | 0.1692 | 0.5384 | 0.3447 | 0.062* | |
C7 | −0.02146 (14) | 0.2819 (3) | 0.35635 (13) | 0.0374 (6) | |
C8 | −0.02904 (17) | 0.4483 (4) | 0.36658 (14) | 0.0454 (7) | |
H8 | −0.0092 | 0.5225 | 0.3375 | 0.054* | |
C9 | −0.06662 (18) | 0.5047 (4) | 0.42075 (16) | 0.0542 (8) | |
C10 | −0.0970 (2) | 0.3898 (4) | 0.46210 (15) | 0.0592 (9) | |
H10 | −0.1228 | 0.4262 | 0.4980 | 0.071* | |
C11 | −0.09039 (19) | 0.2245 (4) | 0.45202 (15) | 0.0538 (8) | |
C12 | −0.05146 (17) | 0.1705 (4) | 0.39875 (14) | 0.0467 (7) | |
H12 | −0.0455 | 0.0588 | 0.3915 | 0.056* | |
C13 | −0.0759 (2) | 0.6871 (4) | 0.4317 (2) | 0.0811 (12) | |
H13A | −0.0327 | 0.7445 | 0.4114 | 0.122* | |
H13B | −0.0741 | 0.7091 | 0.4756 | 0.122* | |
H13C | −0.1267 | 0.7233 | 0.4151 | 0.122* | |
C14 | −0.1251 (3) | 0.1020 (5) | 0.49760 (18) | 0.0875 (13) | |
H14A | −0.0820 | 0.0517 | 0.5206 | 0.131* | |
H14B | −0.1545 | 0.0194 | 0.4753 | 0.131* | |
H14C | −0.1608 | 0.1572 | 0.5258 | 0.131* | |
S2 | 0.40323 (4) | 0.72449 (9) | 0.02986 (3) | 0.04244 (19) | |
O5 | 0.39955 (14) | 0.8897 (2) | 0.01021 (10) | 0.0578 (6) | |
O6 | 0.38793 (14) | 0.5967 (3) | −0.01392 (9) | 0.0610 (6) | |
O7 | 0.40738 (16) | 0.3814 (3) | 0.09201 (14) | 0.0767 (7) | |
O8 | 0.28562 (16) | 0.2925 (3) | 0.08814 (15) | 0.0886 (9) | |
N3 | 0.49231 (14) | 0.6879 (3) | 0.05761 (11) | 0.0437 (6) | |
H3N | 0.5007 (18) | 0.588 (2) | 0.0555 (14) | 0.052* | |
N4 | 0.33469 (18) | 0.4009 (3) | 0.09653 (12) | 0.0542 (6) | |
C15 | 0.33333 (15) | 0.7097 (3) | 0.09236 (13) | 0.0386 (6) | |
C16 | 0.30457 (16) | 0.5622 (4) | 0.11719 (13) | 0.0439 (7) | |
C17 | 0.24623 (18) | 0.5593 (5) | 0.16329 (15) | 0.0552 (8) | |
H17 | 0.2266 | 0.4602 | 0.1784 | 0.066* | |
C18 | 0.21766 (18) | 0.7054 (5) | 0.18641 (17) | 0.0616 (9) | |
H18 | 0.1798 | 0.7049 | 0.2183 | 0.074* | |
C19 | 0.24443 (18) | 0.8513 (5) | 0.16295 (16) | 0.0593 (8) | |
H19 | 0.2243 | 0.9492 | 0.1787 | 0.071* | |
C20 | 0.30193 (17) | 0.8538 (4) | 0.11534 (14) | 0.0489 (8) | |
H20 | 0.3191 | 0.9535 | 0.0991 | 0.059* | |
C21 | 0.52374 (15) | 0.7656 (3) | 0.11202 (12) | 0.0343 (6) | |
C22 | 0.55543 (16) | 0.6691 (4) | 0.15836 (14) | 0.0431 (7) | |
H22 | 0.5518 | 0.5557 | 0.1551 | 0.052* | |
C23 | 0.59271 (17) | 0.7376 (4) | 0.20976 (14) | 0.0457 (7) | |
C24 | 0.59616 (17) | 0.9071 (4) | 0.21341 (14) | 0.0486 (7) | |
H24 | 0.6207 | 0.9549 | 0.2479 | 0.058* | |
C25 | 0.56453 (16) | 1.0072 (4) | 0.16781 (15) | 0.0452 (7) | |
C26 | 0.52802 (16) | 0.9346 (4) | 0.11635 (13) | 0.0418 (7) | |
H26 | 0.5065 | 0.9996 | 0.0849 | 0.050* | |
C27 | 0.6301 (2) | 0.6305 (4) | 0.25904 (16) | 0.0674 (10) | |
H27A | 0.6015 | 0.5284 | 0.2611 | 0.101* | |
H27B | 0.6271 | 0.6847 | 0.2986 | 0.101* | |
H27C | 0.6856 | 0.6101 | 0.2488 | 0.101* | |
C28 | 0.5723 (2) | 1.1911 (4) | 0.17188 (19) | 0.0668 (10) | |
H28A | 0.5320 | 1.2333 | 0.1996 | 0.100* | |
H28B | 0.5650 | 1.2380 | 0.1313 | 0.100* | |
H28C | 0.6250 | 1.2189 | 0.1873 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0409 (4) | 0.0553 (5) | 0.0346 (4) | −0.0001 (3) | −0.0008 (3) | 0.0018 (3) |
O1 | 0.0596 (13) | 0.0618 (14) | 0.0622 (14) | −0.0008 (11) | 0.0025 (11) | 0.0275 (12) |
O2 | 0.0650 (14) | 0.0870 (17) | 0.0424 (12) | 0.0065 (12) | 0.0043 (11) | −0.0184 (12) |
O3 | 0.0751 (14) | 0.0599 (15) | 0.114 (2) | −0.0024 (13) | −0.0071 (16) | −0.0043 (15) |
O4 | 0.096 (2) | 0.0755 (19) | 0.156 (3) | 0.0428 (17) | 0.013 (2) | 0.0038 (19) |
N1 | 0.0412 (13) | 0.0502 (15) | 0.0438 (14) | −0.0084 (12) | −0.0014 (11) | −0.0094 (13) |
N2 | 0.0642 (14) | 0.0532 (13) | 0.0617 (17) | 0.0132 (13) | 0.0073 (14) | 0.0081 (13) |
C1 | 0.0330 (14) | 0.0462 (17) | 0.0378 (14) | 0.0001 (13) | 0.0039 (12) | 0.0016 (14) |
C2 | 0.0381 (15) | 0.0598 (15) | 0.0399 (15) | 0.0035 (13) | 0.0060 (13) | 0.0067 (14) |
C3 | 0.0425 (18) | 0.092 (3) | 0.0492 (19) | 0.0106 (18) | 0.0040 (15) | 0.019 (2) |
C4 | 0.0446 (18) | 0.109 (3) | 0.0433 (18) | −0.014 (2) | −0.0004 (15) | −0.004 (2) |
C5 | 0.0468 (19) | 0.085 (3) | 0.058 (2) | −0.0163 (18) | 0.0061 (17) | −0.020 (2) |
C6 | 0.0425 (16) | 0.058 (2) | 0.0534 (18) | −0.0078 (15) | 0.0032 (14) | −0.0068 (16) |
C7 | 0.0261 (13) | 0.0455 (17) | 0.0407 (15) | 0.0015 (12) | −0.0052 (11) | −0.0030 (13) |
C8 | 0.0401 (16) | 0.0463 (19) | 0.0497 (17) | −0.0005 (13) | −0.0039 (14) | 0.0021 (14) |
C9 | 0.0513 (18) | 0.0493 (19) | 0.062 (2) | 0.0106 (15) | −0.0108 (16) | −0.0082 (17) |
C10 | 0.058 (2) | 0.072 (2) | 0.0484 (18) | 0.0116 (18) | 0.0051 (17) | −0.0093 (17) |
C11 | 0.0498 (18) | 0.067 (2) | 0.0446 (17) | 0.0013 (17) | 0.0011 (15) | 0.0028 (16) |
C12 | 0.0428 (16) | 0.0439 (18) | 0.0535 (18) | −0.0011 (13) | −0.0032 (14) | 0.0026 (15) |
C13 | 0.088 (3) | 0.062 (3) | 0.093 (3) | 0.020 (2) | −0.008 (2) | −0.017 (2) |
C14 | 0.097 (3) | 0.099 (3) | 0.067 (2) | −0.014 (2) | 0.020 (2) | 0.020 (2) |
S2 | 0.0462 (4) | 0.0507 (4) | 0.0305 (3) | −0.0034 (4) | −0.0045 (3) | 0.0018 (3) |
O5 | 0.0634 (14) | 0.0569 (13) | 0.0531 (12) | −0.0055 (11) | −0.0033 (11) | 0.0177 (10) |
O6 | 0.0708 (15) | 0.0708 (15) | 0.0413 (11) | −0.0095 (12) | −0.0052 (11) | −0.0146 (11) |
O7 | 0.0674 (16) | 0.0550 (15) | 0.108 (2) | 0.0121 (12) | 0.0070 (15) | 0.0038 (14) |
O8 | 0.0862 (19) | 0.0584 (16) | 0.121 (2) | −0.0242 (14) | 0.0008 (18) | −0.0154 (16) |
N3 | 0.0415 (13) | 0.0444 (15) | 0.0452 (14) | 0.0019 (12) | 0.0028 (11) | −0.0079 (12) |
N4 | 0.0623 (17) | 0.0468 (14) | 0.0534 (16) | −0.0029 (13) | −0.0035 (14) | 0.0078 (12) |
C15 | 0.0324 (14) | 0.0463 (17) | 0.0369 (15) | −0.0008 (13) | −0.0066 (12) | −0.0018 (13) |
C16 | 0.0399 (15) | 0.0520 (16) | 0.0397 (16) | −0.0037 (13) | −0.0073 (13) | 0.0024 (13) |
C17 | 0.0470 (18) | 0.068 (2) | 0.0505 (19) | −0.0107 (16) | 0.0006 (15) | 0.0065 (17) |
C18 | 0.0378 (16) | 0.094 (2) | 0.0528 (19) | −0.0051 (17) | 0.0027 (15) | −0.0098 (18) |
C19 | 0.0414 (17) | 0.0705 (19) | 0.066 (2) | 0.0048 (14) | −0.0040 (16) | −0.0244 (17) |
C20 | 0.0416 (16) | 0.0505 (19) | 0.0546 (18) | −0.0029 (14) | −0.0067 (15) | −0.0046 (15) |
C21 | 0.0290 (13) | 0.0364 (16) | 0.0376 (14) | −0.0023 (11) | 0.0051 (11) | 0.0011 (12) |
C22 | 0.0425 (16) | 0.0376 (16) | 0.0494 (17) | −0.0002 (12) | 0.0025 (13) | −0.0015 (14) |
C23 | 0.0410 (15) | 0.0537 (19) | 0.0424 (16) | 0.0004 (14) | −0.0013 (14) | 0.0041 (14) |
C24 | 0.0442 (16) | 0.0553 (19) | 0.0464 (17) | −0.0043 (14) | −0.0043 (14) | −0.0058 (15) |
C25 | 0.0410 (16) | 0.0407 (17) | 0.0540 (18) | −0.0055 (13) | 0.0034 (14) | −0.0028 (14) |
C26 | 0.0359 (14) | 0.0437 (18) | 0.0458 (16) | −0.0021 (12) | 0.0015 (13) | 0.0070 (14) |
C27 | 0.071 (2) | 0.073 (2) | 0.058 (2) | 0.0065 (19) | −0.0150 (18) | 0.0135 (18) |
C28 | 0.072 (2) | 0.046 (2) | 0.083 (3) | −0.0094 (16) | −0.002 (2) | −0.0081 (18) |
S1—O1 | 1.420 (2) | S2—O5 | 1.414 (2) |
S1—O2 | 1.427 (2) | S2—O6 | 1.427 (2) |
S1—N1 | 1.617 (2) | S2—N3 | 1.618 (2) |
S1—C1 | 1.783 (3) | S2—C15 | 1.777 (3) |
O3—N2 | 1.212 (3) | O7—N4 | 1.218 (3) |
O4—N2 | 1.213 (3) | O8—N4 | 1.215 (3) |
N1—C7 | 1.425 (3) | N3—C21 | 1.427 (3) |
N1—H1N | 0.819 (17) | N3—H3N | 0.832 (17) |
N2—C2 | 1.463 (4) | N4—C16 | 1.476 (4) |
C1—C2 | 1.379 (4) | C15—C20 | 1.378 (4) |
C1—C6 | 1.392 (4) | C15—C16 | 1.401 (4) |
C2—C3 | 1.393 (4) | C16—C17 | 1.384 (4) |
C3—C4 | 1.378 (5) | C17—C18 | 1.375 (5) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.355 (5) | C18—C19 | 1.367 (5) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.378 (4) | C19—C20 | 1.398 (5) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C12 | 1.380 (4) | C21—C22 | 1.373 (4) |
C7—C8 | 1.381 (4) | C21—C26 | 1.384 (4) |
C8—C9 | 1.398 (4) | C22—C23 | 1.382 (4) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.386 (5) | C23—C24 | 1.386 (4) |
C9—C13 | 1.515 (4) | C23—C27 | 1.506 (4) |
C10—C11 | 1.370 (5) | C24—C25 | 1.378 (4) |
C10—H10 | 0.9300 | C24—H24 | 0.9300 |
C11—C12 | 1.386 (4) | C25—C26 | 1.392 (4) |
C11—C14 | 1.513 (5) | C25—C28 | 1.509 (4) |
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 |
O1—S1—O2 | 118.60 (14) | O5—S2—O6 | 119.54 (13) |
O1—S1—N1 | 107.63 (13) | O5—S2—N3 | 108.96 (13) |
O2—S1—N1 | 107.85 (14) | O6—S2—N3 | 105.60 (13) |
O1—S1—C1 | 105.78 (13) | O5—S2—C15 | 105.19 (13) |
O2—S1—C1 | 108.50 (13) | O6—S2—C15 | 109.43 (13) |
N1—S1—C1 | 108.08 (12) | N3—S2—C15 | 107.66 (12) |
C7—N1—S1 | 122.89 (19) | C21—N3—S2 | 123.45 (19) |
C7—N1—H1N | 115 (2) | C21—N3—H3N | 115 (2) |
S1—N1—H1N | 114 (2) | S2—N3—H3N | 108 (2) |
O3—N2—O4 | 122.5 (3) | O8—N4—O7 | 123.6 (3) |
O3—N2—C2 | 119.2 (3) | O8—N4—C16 | 117.9 (3) |
O4—N2—C2 | 118.2 (3) | O7—N4—C16 | 118.3 (3) |
C2—C1—C6 | 118.2 (3) | C20—C15—C16 | 118.0 (3) |
C2—C1—S1 | 124.6 (2) | C20—C15—S2 | 117.3 (2) |
C6—C1—S1 | 117.1 (2) | C16—C15—S2 | 124.6 (2) |
C1—C2—C3 | 120.8 (3) | C17—C16—C15 | 121.6 (3) |
C1—C2—N2 | 123.2 (3) | C17—C16—N4 | 115.9 (3) |
C3—C2—N2 | 115.9 (3) | C15—C16—N4 | 122.5 (3) |
C4—C3—C2 | 119.4 (3) | C18—C17—C16 | 119.0 (3) |
C4—C3—H3 | 120.3 | C18—C17—H17 | 120.5 |
C2—C3—H3 | 120.3 | C16—C17—H17 | 120.5 |
C5—C4—C3 | 120.4 (3) | C19—C18—C17 | 120.7 (3) |
C5—C4—H4 | 119.8 | C19—C18—H18 | 119.7 |
C3—C4—H4 | 119.8 | C17—C18—H18 | 119.7 |
C4—C5—C6 | 120.4 (3) | C18—C19—C20 | 120.3 (3) |
C4—C5—H5 | 119.8 | C18—C19—H19 | 119.9 |
C6—C5—H5 | 119.8 | C20—C19—H19 | 119.9 |
C5—C6—C1 | 120.8 (3) | C15—C20—C19 | 120.5 (3) |
C5—C6—H6 | 119.6 | C15—C20—H20 | 119.8 |
C1—C6—H6 | 119.6 | C19—C20—H20 | 119.8 |
C12—C7—C8 | 120.7 (3) | C22—C21—C26 | 120.2 (3) |
C12—C7—N1 | 119.1 (3) | C22—C21—N3 | 118.5 (2) |
C8—C7—N1 | 120.2 (3) | C26—C21—N3 | 121.1 (2) |
C7—C8—C9 | 119.8 (3) | C21—C22—C23 | 121.1 (3) |
C7—C8—H8 | 120.1 | C21—C22—H22 | 119.4 |
C9—C8—H8 | 120.1 | C23—C22—H22 | 119.4 |
C10—C9—C8 | 118.2 (3) | C22—C23—C24 | 117.8 (3) |
C10—C9—C13 | 121.9 (3) | C22—C23—C27 | 120.6 (3) |
C8—C9—C13 | 119.9 (3) | C24—C23—C27 | 121.5 (3) |
C11—C10—C9 | 122.4 (3) | C25—C24—C23 | 122.4 (3) |
C11—C10—H10 | 118.8 | C25—C24—H24 | 118.8 |
C9—C10—H10 | 118.8 | C23—C24—H24 | 118.8 |
C10—C11—C12 | 118.7 (3) | C24—C25—C26 | 118.5 (3) |
C10—C11—C14 | 121.2 (3) | C24—C25—C28 | 121.0 (3) |
C12—C11—C14 | 120.1 (3) | C26—C25—C28 | 120.4 (3) |
C7—C12—C11 | 120.2 (3) | C21—C26—C25 | 120.0 (3) |
C7—C12—H12 | 119.9 | C21—C26—H26 | 120.0 |
C11—C12—H12 | 119.9 | C25—C26—H26 | 120.0 |
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 |
O1—S1—N1—C7 | −69.6 (2) | O5—S2—N3—C21 | 64.2 (3) |
O2—S1—N1—C7 | 161.4 (2) | O6—S2—N3—C21 | −166.2 (2) |
C1—S1—N1—C7 | 44.2 (3) | C15—S2—N3—C21 | −49.3 (3) |
O1—S1—C1—C2 | −168.8 (2) | O5—S2—C15—C20 | −10.3 (2) |
O2—S1—C1—C2 | −40.6 (3) | O6—S2—C15—C20 | −139.9 (2) |
N1—S1—C1—C2 | 76.1 (3) | N3—S2—C15—C20 | 105.8 (2) |
O1—S1—C1—C6 | 6.1 (3) | O5—S2—C15—C16 | 165.8 (2) |
O2—S1—C1—C6 | 134.3 (2) | O6—S2—C15—C16 | 36.2 (3) |
N1—S1—C1—C6 | −109.0 (2) | N3—S2—C15—C16 | −78.1 (2) |
C6—C1—C2—C3 | 0.2 (4) | C20—C15—C16—C17 | 0.2 (4) |
S1—C1—C2—C3 | 175.0 (2) | S2—C15—C16—C17 | −175.8 (2) |
C6—C1—C2—N2 | 179.6 (3) | C20—C15—C16—N4 | −179.3 (2) |
S1—C1—C2—N2 | −5.6 (4) | S2—C15—C16—N4 | 4.7 (4) |
O3—N2—C2—C1 | −41.2 (4) | O8—N4—C16—C17 | 43.4 (4) |
O4—N2—C2—C1 | 140.3 (3) | O7—N4—C16—C17 | −132.8 (3) |
O3—N2—C2—C3 | 138.3 (3) | O8—N4—C16—C15 | −137.1 (3) |
O4—N2—C2—C3 | −40.3 (4) | O7—N4—C16—C15 | 46.7 (4) |
C1—C2—C3—C4 | 1.0 (4) | C15—C16—C17—C18 | −1.9 (4) |
N2—C2—C3—C4 | −178.4 (3) | N4—C16—C17—C18 | 177.6 (3) |
C2—C3—C4—C5 | −1.7 (5) | C16—C17—C18—C19 | 2.1 (5) |
C3—C4—C5—C6 | 1.3 (5) | C17—C18—C19—C20 | −0.6 (5) |
C4—C5—C6—C1 | 0.0 (5) | C16—C15—C20—C19 | 1.4 (4) |
C2—C1—C6—C5 | −0.7 (4) | S2—C15—C20—C19 | 177.7 (2) |
S1—C1—C6—C5 | −175.9 (2) | C18—C19—C20—C15 | −1.2 (5) |
S1—N1—C7—C12 | −131.0 (2) | S2—N3—C21—C22 | 128.6 (2) |
S1—N1—C7—C8 | 51.7 (3) | S2—N3—C21—C26 | −56.2 (3) |
C12—C7—C8—C9 | 0.7 (4) | C26—C21—C22—C23 | −0.6 (4) |
N1—C7—C8—C9 | 178.0 (2) | N3—C21—C22—C23 | 174.6 (2) |
C7—C8—C9—C10 | −1.5 (4) | C21—C22—C23—C24 | 0.8 (4) |
C7—C8—C9—C13 | −179.3 (3) | C21—C22—C23—C27 | −177.6 (3) |
C8—C9—C10—C11 | 0.9 (5) | C22—C23—C24—C25 | −0.5 (4) |
C13—C9—C10—C11 | 178.7 (3) | C27—C23—C24—C25 | 177.9 (3) |
C9—C10—C11—C12 | 0.4 (5) | C23—C24—C25—C26 | −0.1 (4) |
C9—C10—C11—C14 | −179.2 (3) | C23—C24—C25—C28 | −177.4 (3) |
C8—C7—C12—C11 | 0.6 (4) | C22—C21—C26—C25 | 0.0 (4) |
N1—C7—C12—C11 | −176.7 (2) | N3—C21—C26—C25 | −175.1 (2) |
C10—C11—C12—C7 | −1.2 (4) | C24—C25—C26—C21 | 0.3 (4) |
C14—C11—C12—C7 | 178.4 (3) | C28—C25—C26—C21 | 177.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.82 (2) | 2.40 (2) | 3.089 (3) | 142 (3) |
N1—H1N···O3 | 0.82 (2) | 2.52 (3) | 2.893 (4) | 109 (2) |
N3—H3N···O7 | 0.83 (2) | 2.42 (3) | 2.963 (3) | 124 (3) |
N3—H3N···O6ii | 0.83 (2) | 2.54 (2) | 3.195 (3) | 136 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O4S |
Mr | 306.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.561 (1), 8.1611 (6), 21.476 (2) |
β (°) | 90.056 (7) |
V (Å3) | 2902.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.48 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.894, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12941, 5929, 4004 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.123, 1.00 |
No. of reflections | 5929 |
No. of parameters | 390 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.29 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.819 (17) | 2.40 (2) | 3.089 (3) | 142 (3) |
N1—H1N···O3 | 0.819 (17) | 2.52 (3) | 2.893 (4) | 109 (2) |
N3—H3N···O7 | 0.832 (17) | 2.42 (3) | 2.963 (3) | 124 (3) |
N3—H3N···O6ii | 0.832 (17) | 2.54 (2) | 3.195 (3) | 136 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z. |
Acknowledgements
UC thanks Mangalore University for 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
Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
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Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160. CSD CrossRef IUCr Journals Google Scholar
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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)-2-nitrobenzenesulfonamide has been determined.
The asymmetric unit of the title compound consists of two crystallographically independent molecules (Fig. 1). The conformation of the N—C bond in the —SO2—NH—C segment has gauche torsions with respect to the S═O bonds, similar to that observed in N-(3-methylphenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). Further, the conformation of the N—H bond in the —SO2—NH— segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The molecules are twisted at the S—N bonds with C1—S1—N1—C7 and C15—S2—N3—C21 torsion angles of 44.2 (3) and -49.3 (3)°, respectively, compared to the value of 46.97 (16)° in (I). The dihedral angles between the sulfonyl and the anilino rings in the two molecules are 71.53 (7) and 72.11 (7)°, compared to the value of 73.64 (7)° in (I). In each molecule the amide H atom shows an intramolecular hydrogen bond (N1—H1N···O1 and N3—H3N···O7; Table 1) with the O atom of the ortho-nitro group in the sulfonyl benzene ring, generating an S(7) motif (Adsmond et al., 2001). In the crystal, the amide H atoms show intermolecular hydrogen bonds with the sulfonyl oxygen atoms of the other molecule; the N1—H1N···O1i hydrogen bond (symmetry code in Table 1) generates a C(4) motif and a helical chain along the b axis, while the N3—H3N···O6ii hydrogen bond (symmetry code in Table 1) an R22(8) motif and an inversion dimer. A part of the crystal structure is shown in Fig. 2.