


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810011669/ci5070sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810011669/ci5070Isup2.hkl |
CCDC reference: 777934
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.058
- wR factor = 0.161
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 -- C22 .. 5.42 su PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 5 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 37 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 26
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The solution of m-xylene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 273 K. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dimethylbenzenesulfonylchloride was treated with a stoichiometric amount of 2,3-dimethylaniline and boiled for 10 min. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid 2,4-dimethyl-N- (2,3-dimethylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.
H atoms of the NH groups were located in a difference map and their positional parameters were refined [N–H = 0.79 (3)–0.83 (3) Å]. The other H atoms were positioned with idealized geometry using a riding model with C–H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
As part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a,b,c), in the present work, the structure of 2,4-dimethyl-N-(2,3-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit contains two independent molecules. Both molecules are bent at the N-atoms with C—SO2—NH—C torsion angles of 70.1 (2) and -66.0 (2)°, compared to the values of 53.9 (2)° in 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (II) (Gowda et al., 2009c), 71.0 (2)° in N-(2,3-dimethylphenyl)benzenesulfonamide (III) (Gowda et al., 2009a), and 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (IV) (Gowda et al., 2009b).
The sulfonyl and anilino benzene rings in the two molecules of (I) are tilted relative to each other by 41.5 (1) and 43.8 (1)° in (I), compared to the values of 82.1 (1)° in (II), 64.8 (1)° in (III), and 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of (IV), The remaining bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).
In the crystal structure, pairs of intermolecular N—H···O hydrogen bonds (Table 1) link the independent molecules to form dimers as shown in Fig. 1 and Fig.2.
For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009a,b,c). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (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).
C16H19NO2S | Z = 4 |
Mr = 289.38 | F(000) = 616 |
Triclinic, P1 | Dx = 1.270 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3643 (7) Å | Cell parameters from 3007 reflections |
b = 10.975 (1) Å | θ = 2.5–28.0° |
c = 16.996 (2) Å | µ = 0.22 mm−1 |
α = 83.034 (9)° | T = 299 K |
β = 80.100 (7)° | Prism, yellow |
γ = 81.796 (9)° | 0.34 × 0.30 × 0.20 mm |
V = 1513.7 (3) Å3 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 6136 independent reflections |
Radiation source: fine-focus sealed tube | 4196 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Rotation method data acquisition using ω and φ scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −10→10 |
Tmin = 0.931, Tmax = 0.958 | k = −13→13 |
11164 measured reflections | l = −21→21 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0699P)2 + 0.9151P] where P = (Fo2 + 2Fc2)/3 |
6136 reflections | (Δ/σ)max = 0.002 |
375 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C16H19NO2S | γ = 81.796 (9)° |
Mr = 289.38 | V = 1513.7 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.3643 (7) Å | Mo Kα radiation |
b = 10.975 (1) Å | µ = 0.22 mm−1 |
c = 16.996 (2) Å | T = 299 K |
α = 83.034 (9)° | 0.34 × 0.30 × 0.20 mm |
β = 80.100 (7)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 6136 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 4196 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.958 | Rint = 0.016 |
11164 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.66 e Å−3 |
6136 reflections | Δρmin = −0.41 e Å−3 |
375 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
C1 | 0.7579 (3) | 0.1917 (2) | 0.30498 (15) | 0.0439 (6) | |
C2 | 0.8079 (3) | 0.0826 (2) | 0.35144 (17) | 0.0487 (6) | |
C3 | 0.6896 (4) | 0.0046 (3) | 0.38031 (18) | 0.0559 (7) | |
H3 | 0.7200 | −0.0685 | 0.4110 | 0.067* | |
C4 | 0.5295 (4) | 0.0283 (3) | 0.36652 (18) | 0.0548 (7) | |
C5 | 0.4848 (4) | 0.1366 (3) | 0.32071 (19) | 0.0582 (8) | |
H5 | 0.3781 | 0.1550 | 0.3101 | 0.070* | |
C6 | 0.5965 (3) | 0.2167 (3) | 0.29087 (18) | 0.0532 (7) | |
H6 | 0.5642 | 0.2895 | 0.2605 | 0.064* | |
C7 | 0.9403 (3) | 0.3704 (2) | 0.40309 (15) | 0.0405 (6) | |
C8 | 1.1020 (3) | 0.3881 (2) | 0.40397 (16) | 0.0431 (6) | |
C9 | 1.1659 (4) | 0.3549 (3) | 0.47568 (18) | 0.0532 (7) | |
C10 | 1.0649 (5) | 0.3099 (3) | 0.54282 (18) | 0.0649 (9) | |
H10 | 1.1067 | 0.2888 | 0.5906 | 0.078* | |
C11 | 0.9048 (5) | 0.2950 (3) | 0.54161 (19) | 0.0664 (9) | |
H11 | 0.8397 | 0.2652 | 0.5880 | 0.080* | |
C12 | 0.8422 (4) | 0.3247 (3) | 0.47111 (18) | 0.0545 (7) | |
H12 | 0.7346 | 0.3142 | 0.4692 | 0.065* | |
C13 | 0.9783 (4) | 0.0452 (3) | 0.3710 (2) | 0.0703 (9) | |
H13A | 1.0148 | 0.1136 | 0.3902 | 0.084* | |
H13B | 1.0510 | 0.0220 | 0.3235 | 0.084* | |
H13C | 0.9778 | −0.0236 | 0.4116 | 0.084* | |
C14 | 0.4087 (4) | −0.0607 (3) | 0.4010 (2) | 0.0770 (10) | |
H14A | 0.4628 | −0.1313 | 0.4293 | 0.092* | |
H14B | 0.3640 | −0.0869 | 0.3584 | 0.092* | |
H14C | 0.3221 | −0.0206 | 0.4374 | 0.092* | |
C15 | 1.2017 (4) | 0.4467 (3) | 0.33078 (19) | 0.0594 (8) | |
H15A | 1.1299 | 0.4970 | 0.2980 | 0.071* | |
H15B | 1.2662 | 0.3833 | 0.3007 | 0.071* | |
H15C | 1.2725 | 0.4973 | 0.3469 | 0.071* | |
C16 | 1.3387 (4) | 0.3701 (4) | 0.4809 (2) | 0.0815 (11) | |
H16A | 1.3584 | 0.4534 | 0.4616 | 0.098* | |
H16B | 1.4123 | 0.3136 | 0.4486 | 0.098* | |
H16C | 1.3563 | 0.3531 | 0.5357 | 0.098* | |
N1 | 0.8735 (3) | 0.4042 (2) | 0.32974 (14) | 0.0487 (6) | |
H1N | 0.783 (4) | 0.447 (3) | 0.3348 (18) | 0.058* | |
O1 | 0.8196 (3) | 0.37379 (19) | 0.19753 (12) | 0.0638 (6) | |
O2 | 1.0524 (2) | 0.24770 (19) | 0.25134 (12) | 0.0596 (5) | |
S1 | 0.88758 (9) | 0.30509 (6) | 0.26408 (4) | 0.0484 (2) | |
C17 | 0.6666 (3) | 0.7822 (2) | 0.21219 (16) | 0.0459 (6) | |
C18 | 0.6232 (3) | 0.8894 (2) | 0.16309 (18) | 0.0503 (7) | |
C19 | 0.7455 (4) | 0.9638 (3) | 0.1334 (2) | 0.0621 (8) | |
H19 | 0.7199 | 1.0352 | 0.1002 | 0.075* | |
C20 | 0.9028 (4) | 0.9375 (3) | 0.1505 (2) | 0.0621 (8) | |
C21 | 0.9409 (4) | 0.8305 (3) | 0.1997 (2) | 0.0644 (9) | |
H21 | 1.0461 | 0.8107 | 0.2122 | 0.077* | |
C22 | 0.8243 (4) | 0.7539 (3) | 0.22987 (18) | 0.0552 (7) | |
H22 | 0.8512 | 0.6821 | 0.2625 | 0.066* | |
C23 | 0.4896 (3) | 0.6176 (2) | 0.10779 (15) | 0.0403 (6) | |
C24 | 0.6025 (3) | 0.6394 (2) | 0.03794 (16) | 0.0427 (6) | |
C25 | 0.5393 (4) | 0.6793 (2) | −0.03382 (17) | 0.0523 (7) | |
C26 | 0.3736 (4) | 0.6952 (3) | −0.0335 (2) | 0.0615 (8) | |
H26 | 0.3337 | 0.7213 | −0.0813 | 0.074* | |
C27 | 0.2650 (4) | 0.6736 (3) | 0.0354 (2) | 0.0628 (8) | |
H27 | 0.1531 | 0.6862 | 0.0342 | 0.075* | |
C28 | 0.3231 (3) | 0.6332 (3) | 0.10660 (18) | 0.0526 (7) | |
H28 | 0.2506 | 0.6166 | 0.1534 | 0.063* | |
C29 | 0.4565 (4) | 0.9307 (3) | 0.1406 (2) | 0.0710 (10) | |
H29A | 0.3803 | 0.9503 | 0.1878 | 0.085* | |
H29B | 0.4219 | 0.8656 | 0.1172 | 0.085* | |
H29C | 0.4609 | 1.0028 | 0.1026 | 0.085* | |
C30 | 1.0290 (5) | 1.0232 (4) | 0.1153 (3) | 0.0918 (12) | |
H30A | 1.0768 | 1.0470 | 0.1577 | 0.110* | |
H30B | 0.9775 | 1.0955 | 0.0875 | 0.110* | |
H30C | 1.1128 | 0.9813 | 0.0784 | 0.110* | |
C31 | 0.7824 (3) | 0.6221 (3) | 0.03934 (18) | 0.0588 (8) | |
H31A | 0.8049 | 0.5729 | 0.0878 | 0.071* | |
H31B | 0.8197 | 0.7014 | 0.0373 | 0.071* | |
H31C | 0.8382 | 0.5810 | −0.0062 | 0.071* | |
C32 | 0.6546 (5) | 0.7030 (3) | −0.11119 (19) | 0.0778 (10) | |
H32A | 0.7213 | 0.6273 | −0.1243 | 0.093* | |
H32B | 0.7232 | 0.7631 | −0.1049 | 0.093* | |
H32C | 0.5925 | 0.7337 | −0.1536 | 0.093* | |
N2 | 0.5434 (3) | 0.5754 (2) | 0.18338 (14) | 0.0469 (5) | |
H2N | 0.627 (4) | 0.532 (3) | 0.1814 (18) | 0.056* | |
O3 | 0.5930 (3) | 0.59831 (19) | 0.31781 (12) | 0.0651 (6) | |
O4 | 0.3674 (2) | 0.73252 (18) | 0.26308 (12) | 0.0575 (5) | |
S2 | 0.53042 (9) | 0.67152 (6) | 0.25099 (4) | 0.0487 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0468 (15) | 0.0455 (14) | 0.0409 (15) | 0.0010 (11) | −0.0121 (11) | −0.0104 (12) |
C2 | 0.0506 (16) | 0.0447 (14) | 0.0516 (16) | 0.0046 (12) | −0.0169 (13) | −0.0076 (12) |
C3 | 0.0653 (19) | 0.0428 (15) | 0.0594 (19) | −0.0036 (13) | −0.0149 (15) | −0.0011 (13) |
C4 | 0.0581 (18) | 0.0546 (16) | 0.0546 (18) | −0.0077 (14) | −0.0093 (14) | −0.0154 (14) |
C5 | 0.0461 (16) | 0.0651 (18) | 0.066 (2) | −0.0035 (14) | −0.0159 (14) | −0.0128 (16) |
C6 | 0.0520 (16) | 0.0534 (16) | 0.0555 (18) | 0.0040 (13) | −0.0212 (13) | −0.0045 (13) |
C7 | 0.0483 (15) | 0.0314 (12) | 0.0427 (14) | −0.0057 (10) | −0.0086 (11) | −0.0037 (10) |
C8 | 0.0499 (15) | 0.0370 (13) | 0.0423 (15) | −0.0060 (11) | −0.0057 (11) | −0.0051 (11) |
C9 | 0.0568 (17) | 0.0502 (15) | 0.0555 (18) | 0.0025 (13) | −0.0174 (14) | −0.0156 (14) |
C10 | 0.100 (3) | 0.0516 (17) | 0.0416 (17) | 0.0086 (17) | −0.0207 (17) | −0.0049 (14) |
C11 | 0.096 (3) | 0.0519 (17) | 0.0432 (18) | −0.0120 (17) | 0.0093 (16) | 0.0029 (14) |
C12 | 0.0590 (18) | 0.0488 (15) | 0.0526 (18) | −0.0138 (13) | 0.0055 (13) | −0.0047 (13) |
C13 | 0.061 (2) | 0.0565 (18) | 0.094 (3) | 0.0012 (15) | −0.0319 (18) | 0.0124 (17) |
C14 | 0.073 (2) | 0.077 (2) | 0.086 (3) | −0.0253 (18) | −0.0081 (19) | −0.010 (2) |
C15 | 0.0515 (17) | 0.0656 (18) | 0.0616 (19) | −0.0195 (14) | −0.0001 (14) | −0.0060 (15) |
C16 | 0.065 (2) | 0.099 (3) | 0.089 (3) | 0.0086 (19) | −0.0332 (19) | −0.036 (2) |
N1 | 0.0485 (13) | 0.0439 (12) | 0.0538 (14) | 0.0008 (10) | −0.0144 (11) | −0.0041 (11) |
O1 | 0.0778 (14) | 0.0661 (13) | 0.0476 (12) | −0.0039 (11) | −0.0223 (10) | 0.0064 (10) |
O2 | 0.0529 (12) | 0.0671 (13) | 0.0570 (13) | −0.0047 (10) | −0.0030 (9) | −0.0103 (10) |
S1 | 0.0531 (4) | 0.0499 (4) | 0.0421 (4) | −0.0027 (3) | −0.0118 (3) | −0.0021 (3) |
C17 | 0.0507 (16) | 0.0436 (14) | 0.0448 (15) | −0.0017 (12) | −0.0113 (12) | −0.0093 (12) |
C18 | 0.0495 (16) | 0.0418 (14) | 0.0612 (18) | −0.0015 (12) | −0.0141 (13) | −0.0090 (13) |
C19 | 0.064 (2) | 0.0461 (16) | 0.078 (2) | −0.0048 (14) | −0.0169 (16) | −0.0052 (15) |
C20 | 0.0514 (18) | 0.0637 (19) | 0.075 (2) | −0.0111 (14) | −0.0056 (15) | −0.0245 (17) |
C21 | 0.0495 (17) | 0.074 (2) | 0.075 (2) | 0.0061 (15) | −0.0213 (16) | −0.0271 (18) |
C22 | 0.0545 (17) | 0.0564 (17) | 0.0567 (18) | 0.0027 (14) | −0.0185 (14) | −0.0110 (14) |
C23 | 0.0491 (15) | 0.0332 (12) | 0.0379 (14) | −0.0036 (10) | −0.0058 (11) | −0.0042 (10) |
C24 | 0.0499 (15) | 0.0365 (12) | 0.0429 (15) | −0.0088 (11) | −0.0066 (11) | −0.0058 (11) |
C25 | 0.073 (2) | 0.0433 (14) | 0.0434 (16) | −0.0117 (13) | −0.0124 (14) | −0.0041 (12) |
C26 | 0.080 (2) | 0.0523 (17) | 0.058 (2) | −0.0022 (15) | −0.0328 (17) | −0.0041 (14) |
C27 | 0.0535 (18) | 0.0624 (19) | 0.079 (2) | −0.0035 (14) | −0.0242 (17) | −0.0161 (17) |
C28 | 0.0459 (16) | 0.0538 (16) | 0.0580 (18) | −0.0101 (12) | −0.0029 (13) | −0.0086 (14) |
C29 | 0.0588 (19) | 0.0538 (18) | 0.100 (3) | −0.0028 (15) | −0.0298 (18) | 0.0126 (18) |
C30 | 0.067 (2) | 0.090 (3) | 0.124 (4) | −0.025 (2) | −0.008 (2) | −0.024 (2) |
C31 | 0.0499 (17) | 0.0703 (19) | 0.0556 (18) | −0.0144 (14) | 0.0005 (13) | −0.0076 (15) |
C32 | 0.109 (3) | 0.077 (2) | 0.0454 (19) | −0.022 (2) | −0.0035 (18) | 0.0044 (17) |
N2 | 0.0525 (14) | 0.0437 (12) | 0.0413 (13) | −0.0003 (10) | −0.0061 (11) | −0.0001 (10) |
O3 | 0.0854 (15) | 0.0675 (13) | 0.0381 (11) | 0.0013 (11) | −0.0128 (10) | 0.0030 (10) |
O4 | 0.0536 (12) | 0.0617 (12) | 0.0523 (12) | −0.0006 (9) | 0.0027 (9) | −0.0089 (10) |
S2 | 0.0574 (4) | 0.0501 (4) | 0.0362 (4) | −0.0020 (3) | −0.0062 (3) | −0.0025 (3) |
C1—C6 | 1.395 (4) | C17—C22 | 1.386 (4) |
C1—C2 | 1.405 (4) | C17—C18 | 1.399 (4) |
C1—S1 | 1.768 (3) | C17—S2 | 1.775 (3) |
C2—C3 | 1.387 (4) | C18—C19 | 1.389 (4) |
C2—C13 | 1.508 (4) | C18—C29 | 1.501 (4) |
C3—C4 | 1.382 (4) | C19—C20 | 1.379 (4) |
C3—H3 | 0.93 | C19—H19 | 0.93 |
C4—C5 | 1.381 (4) | C20—C21 | 1.388 (4) |
C4—C14 | 1.502 (4) | C20—C30 | 1.512 (5) |
C5—C6 | 1.366 (4) | C21—C22 | 1.371 (4) |
C5—H5 | 0.93 | C21—H21 | 0.93 |
C6—H6 | 0.93 | C22—H22 | 0.93 |
C7—C12 | 1.383 (4) | C23—C28 | 1.382 (4) |
C7—C8 | 1.397 (3) | C23—C24 | 1.403 (4) |
C7—N1 | 1.440 (3) | C23—N2 | 1.437 (3) |
C8—C9 | 1.402 (4) | C24—C25 | 1.409 (4) |
C8—C15 | 1.503 (4) | C24—C31 | 1.493 (4) |
C9—C10 | 1.382 (4) | C25—C26 | 1.372 (4) |
C9—C16 | 1.497 (4) | C25—C32 | 1.509 (4) |
C10—C11 | 1.376 (5) | C26—C27 | 1.371 (5) |
C10—H10 | 0.93 | C26—H26 | 0.93 |
C11—C12 | 1.374 (4) | C27—C28 | 1.381 (4) |
C11—H11 | 0.93 | C27—H27 | 0.93 |
C12—H12 | 0.93 | C28—H28 | 0.93 |
C13—H13A | 0.96 | C29—H29A | 0.96 |
C13—H13B | 0.96 | C29—H29B | 0.96 |
C13—H13C | 0.96 | C29—H29C | 0.96 |
C14—H14A | 0.96 | C30—H30A | 0.96 |
C14—H14B | 0.96 | C30—H30B | 0.96 |
C14—H14C | 0.96 | C30—H30C | 0.96 |
C15—H15A | 0.96 | C31—H31A | 0.96 |
C15—H15B | 0.96 | C31—H31B | 0.96 |
C15—H15C | 0.96 | C31—H31C | 0.96 |
C16—H16A | 0.96 | C32—H32A | 0.96 |
C16—H16B | 0.96 | C32—H32B | 0.96 |
C16—H16C | 0.96 | C32—H32C | 0.96 |
N1—S1 | 1.630 (2) | N2—S2 | 1.632 (2) |
N1—H1N | 0.83 (3) | N2—H2N | 0.79 (3) |
O1—S1 | 1.436 (2) | O3—S2 | 1.439 (2) |
O2—S1 | 1.424 (2) | O4—S2 | 1.423 (2) |
C6—C1—C2 | 119.8 (3) | C22—C17—C18 | 120.8 (3) |
C6—C1—S1 | 116.4 (2) | C22—C17—S2 | 116.1 (2) |
C2—C1—S1 | 123.8 (2) | C18—C17—S2 | 123.0 (2) |
C3—C2—C1 | 116.4 (2) | C19—C18—C17 | 116.6 (3) |
C3—C2—C13 | 118.8 (3) | C19—C18—C29 | 117.8 (3) |
C1—C2—C13 | 124.8 (3) | C17—C18—C29 | 125.7 (3) |
C4—C3—C2 | 124.3 (3) | C20—C19—C18 | 123.6 (3) |
C4—C3—H3 | 117.9 | C20—C19—H19 | 118.2 |
C2—C3—H3 | 117.9 | C18—C19—H19 | 118.2 |
C5—C4—C3 | 117.7 (3) | C19—C20—C21 | 118.1 (3) |
C5—C4—C14 | 121.5 (3) | C19—C20—C30 | 120.2 (3) |
C3—C4—C14 | 120.8 (3) | C21—C20—C30 | 121.7 (3) |
C6—C5—C4 | 120.3 (3) | C22—C21—C20 | 120.3 (3) |
C6—C5—H5 | 119.8 | C22—C21—H21 | 119.8 |
C4—C5—H5 | 119.8 | C20—C21—H21 | 119.8 |
C5—C6—C1 | 121.5 (3) | C21—C22—C17 | 120.7 (3) |
C5—C6—H6 | 119.3 | C21—C22—H22 | 119.7 |
C1—C6—H6 | 119.3 | C17—C22—H22 | 119.7 |
C12—C7—C8 | 121.8 (3) | C28—C23—C24 | 121.7 (2) |
C12—C7—N1 | 119.5 (2) | C28—C23—N2 | 117.3 (2) |
C8—C7—N1 | 118.7 (2) | C24—C23—N2 | 120.9 (2) |
C7—C8—C9 | 118.3 (2) | C23—C24—C25 | 117.3 (2) |
C7—C8—C15 | 120.5 (2) | C23—C24—C31 | 121.6 (2) |
C9—C8—C15 | 121.1 (3) | C25—C24—C31 | 121.1 (3) |
C10—C9—C8 | 118.7 (3) | C26—C25—C24 | 120.0 (3) |
C10—C9—C16 | 120.1 (3) | C26—C25—C32 | 120.1 (3) |
C8—C9—C16 | 121.2 (3) | C24—C25—C32 | 119.8 (3) |
C11—C10—C9 | 122.5 (3) | C25—C26—C27 | 121.9 (3) |
C11—C10—H10 | 118.8 | C25—C26—H26 | 119.1 |
C9—C10—H10 | 118.8 | C27—C26—H26 | 119.1 |
C12—C11—C10 | 119.2 (3) | C26—C27—C28 | 119.5 (3) |
C12—C11—H11 | 120.4 | C26—C27—H27 | 120.2 |
C10—C11—H11 | 120.4 | C28—C27—H27 | 120.2 |
C11—C12—C7 | 119.5 (3) | C27—C28—C23 | 119.6 (3) |
C11—C12—H12 | 120.2 | C27—C28—H28 | 120.2 |
C7—C12—H12 | 120.2 | C23—C28—H28 | 120.2 |
C2—C13—H13A | 109.5 | C18—C29—H29A | 109.5 |
C2—C13—H13B | 109.5 | C18—C29—H29B | 109.5 |
H13A—C13—H13B | 109.5 | H29A—C29—H29B | 109.5 |
C2—C13—H13C | 109.5 | C18—C29—H29C | 109.5 |
H13A—C13—H13C | 109.5 | H29A—C29—H29C | 109.5 |
H13B—C13—H13C | 109.5 | H29B—C29—H29C | 109.5 |
C4—C14—H14A | 109.5 | C20—C30—H30A | 109.5 |
C4—C14—H14B | 109.5 | C20—C30—H30B | 109.5 |
H14A—C14—H14B | 109.5 | H30A—C30—H30B | 109.5 |
C4—C14—H14C | 109.5 | C20—C30—H30C | 109.5 |
H14A—C14—H14C | 109.5 | H30A—C30—H30C | 109.5 |
H14B—C14—H14C | 109.5 | H30B—C30—H30C | 109.5 |
C8—C15—H15A | 109.5 | C24—C31—H31A | 109.5 |
C8—C15—H15B | 109.5 | C24—C31—H31B | 109.5 |
H15A—C15—H15B | 109.5 | H31A—C31—H31B | 109.5 |
C8—C15—H15C | 109.5 | C24—C31—H31C | 109.5 |
H15A—C15—H15C | 109.5 | H31A—C31—H31C | 109.5 |
H15B—C15—H15C | 109.5 | H31B—C31—H31C | 109.5 |
C9—C16—H16A | 109.5 | C25—C32—H32A | 109.5 |
C9—C16—H16B | 109.5 | C25—C32—H32B | 109.5 |
H16A—C16—H16B | 109.5 | H32A—C32—H32B | 109.5 |
C9—C16—H16C | 109.5 | C25—C32—H32C | 109.5 |
H16A—C16—H16C | 109.5 | H32A—C32—H32C | 109.5 |
H16B—C16—H16C | 109.5 | H32B—C32—H32C | 109.5 |
C7—N1—S1 | 121.05 (17) | C23—N2—S2 | 120.16 (17) |
C7—N1—H1N | 115 (2) | C23—N2—H2N | 116 (2) |
S1—N1—H1N | 112 (2) | S2—N2—H2N | 110 (2) |
O2—S1—O1 | 119.10 (13) | O4—S2—O3 | 118.80 (13) |
O2—S1—N1 | 107.81 (12) | O4—S2—N2 | 108.11 (12) |
O1—S1—N1 | 105.08 (12) | O3—S2—N2 | 104.97 (12) |
O2—S1—C1 | 109.11 (12) | O4—S2—C17 | 109.21 (12) |
O1—S1—C1 | 107.12 (13) | O3—S2—C17 | 107.64 (13) |
N1—S1—C1 | 108.16 (12) | N2—S2—C17 | 107.58 (12) |
C6—C1—C2—C3 | 0.5 (4) | C22—C17—C18—C19 | 0.3 (4) |
S1—C1—C2—C3 | 178.7 (2) | S2—C17—C18—C19 | −176.3 (2) |
C6—C1—C2—C13 | −179.9 (3) | C22—C17—C18—C29 | −179.1 (3) |
S1—C1—C2—C13 | −1.8 (4) | S2—C17—C18—C29 | 4.2 (4) |
C1—C2—C3—C4 | −0.4 (4) | C17—C18—C19—C20 | −0.6 (5) |
C13—C2—C3—C4 | −180.0 (3) | C29—C18—C19—C20 | 178.9 (3) |
C2—C3—C4—C5 | 0.3 (4) | C18—C19—C20—C21 | 0.3 (5) |
C2—C3—C4—C14 | −179.2 (3) | C18—C19—C20—C30 | 179.7 (3) |
C3—C4—C5—C6 | −0.3 (4) | C19—C20—C21—C22 | 0.1 (5) |
C14—C4—C5—C6 | 179.2 (3) | C30—C20—C21—C22 | −179.2 (3) |
C4—C5—C6—C1 | 0.5 (4) | C20—C21—C22—C17 | −0.4 (5) |
C2—C1—C6—C5 | −0.6 (4) | C18—C17—C22—C21 | 0.1 (4) |
S1—C1—C6—C5 | −178.9 (2) | S2—C17—C22—C21 | 177.0 (2) |
C12—C7—C8—C9 | 1.9 (4) | C28—C23—C24—C25 | 0.6 (4) |
N1—C7—C8—C9 | 180.0 (2) | N2—C23—C24—C25 | 179.3 (2) |
C12—C7—C8—C15 | −175.4 (2) | C28—C23—C24—C31 | −179.8 (2) |
N1—C7—C8—C15 | 2.7 (4) | N2—C23—C24—C31 | −1.2 (4) |
C7—C8—C9—C10 | −2.0 (4) | C23—C24—C25—C26 | −0.1 (4) |
C15—C8—C9—C10 | 175.2 (3) | C31—C24—C25—C26 | −179.6 (3) |
C7—C8—C9—C16 | 179.4 (3) | C23—C24—C25—C32 | −179.3 (3) |
C15—C8—C9—C16 | −3.4 (4) | C31—C24—C25—C32 | 1.1 (4) |
C8—C9—C10—C11 | 0.9 (4) | C24—C25—C26—C27 | 0.2 (4) |
C16—C9—C10—C11 | 179.4 (3) | C32—C25—C26—C27 | 179.5 (3) |
C9—C10—C11—C12 | 0.6 (5) | C25—C26—C27—C28 | −0.9 (5) |
C10—C11—C12—C7 | −0.8 (4) | C26—C27—C28—C23 | 1.4 (4) |
C8—C7—C12—C11 | −0.4 (4) | C24—C23—C28—C27 | −1.3 (4) |
N1—C7—C12—C11 | −178.5 (2) | N2—C23—C28—C27 | 180.0 (2) |
C12—C7—N1—S1 | −91.8 (3) | C28—C23—N2—S2 | −77.9 (3) |
C8—C7—N1—S1 | 90.0 (3) | C24—C23—N2—S2 | 103.4 (2) |
C7—N1—S1—O2 | −47.8 (2) | C23—N2—S2—O4 | 51.8 (2) |
C7—N1—S1—O1 | −175.8 (2) | C23—N2—S2—O3 | 179.5 (2) |
C7—N1—S1—C1 | 70.1 (2) | C23—N2—S2—C17 | −66.0 (2) |
C6—C1—S1—O2 | −154.2 (2) | C22—C17—S2—O4 | 152.1 (2) |
C2—C1—S1—O2 | 27.5 (3) | C18—C17—S2—O4 | −31.1 (3) |
C6—C1—S1—O1 | −24.0 (2) | C22—C17—S2—O3 | 21.9 (2) |
C2—C1—S1—O1 | 157.7 (2) | C18—C17—S2—O3 | −161.3 (2) |
C6—C1—S1—N1 | 88.8 (2) | C22—C17—S2—N2 | −90.8 (2) |
C2—C1—S1—N1 | −89.5 (2) | C18—C17—S2—N2 | 86.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.83 (3) | 2.15 (3) | 2.952 (3) | 161 (3) |
N2—H2N···O1 | 0.79 (3) | 2.22 (3) | 2.982 (3) | 164 (3) |
Experimental details
Crystal data | |
Chemical formula | C16H19NO2S |
Mr | 289.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 299 |
a, b, c (Å) | 8.3643 (7), 10.975 (1), 16.996 (2) |
α, β, γ (°) | 83.034 (9), 80.100 (7), 81.796 (9) |
V (Å3) | 1513.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.34 × 0.30 × 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 | 0.931, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11164, 6136, 4196 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.161, 1.03 |
No. of reflections | 6136 |
No. of parameters | 375 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.66, −0.41 |
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···O3 | 0.83 (3) | 2.15 (3) | 2.952 (3) | 161 (3) |
N2—H2N···O1 | 0.79 (3) | 2.22 (3) | 2.982 (3) | 164 (3) |
As part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a,b,c), in the present work, the structure of 2,4-dimethyl-N-(2,3-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit contains two independent molecules. Both molecules are bent at the N-atoms with C—SO2—NH—C torsion angles of 70.1 (2) and -66.0 (2)°, compared to the values of 53.9 (2)° in 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (II) (Gowda et al., 2009c), 71.0 (2)° in N-(2,3-dimethylphenyl)benzenesulfonamide (III) (Gowda et al., 2009a), and 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (IV) (Gowda et al., 2009b).
The sulfonyl and anilino benzene rings in the two molecules of (I) are tilted relative to each other by 41.5 (1) and 43.8 (1)° in (I), compared to the values of 82.1 (1)° in (II), 64.8 (1)° in (III), and 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of (IV), The remaining bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).
In the crystal structure, pairs of intermolecular N—H···O hydrogen bonds (Table 1) link the independent molecules to form dimers as shown in Fig. 1 and Fig.2.