Literature DB >> 21522988

N-(4-Meth-oxy-phen-yl)benzene-sulfonamide.

Saba Ibrahim, M Nawaz Tahir, Nadeem Iqbal, Durre Shahwar, Muhammad Asam Raza.   

Abstract

In the title compound, C(13)H(13)NO(3)S, the benzene ring of the benzene-sulfonamide moiety is disordered with an occupancy ratio of 0.56 (3):0.44 (3), the disorder components being twisted at and angle of 21 (1)° to each other. The meth-oxy-benzene group is roughly planar (r.m.s. deviation = 0.0144 Å) and the amide N atom is displaced from this plane by 0.090 (6) Å. The dihedral angles between the meth-oxy-benzene group and the major and minor occupancy components of the disordered benzene ring are 54.6 (4) and 62.9 (5)°, respectively. In the crystal, infinite polymeric chains are formed along [100] due to inter-molecular N-H⋯O hydrogen bonding. Weak C-H⋯π inter-actions are also present in the crystal.

Entities:  

Year:  2011        PMID： 21522988      PMCID： PMC3051711          DOI： 10.1107/S1600536811000365

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Kato et al. (2006 ▶); Perlovich et al. (2009 ▶).

Experimental

Crystal data

C13H13NO3S M = 263.30 Orthorhombic, a = 5.3094 (5) Å b = 8.5309 (10) Å c = 27.925 (3) Å V = 1264.8 (2) Å3 Z = 4 Mo Kα radiation μ = 0.26 mm−1 T = 296 K 0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.961, T max = 0.970 7272 measured reflections 2457 independent reflections 1503 reflections with I > 2σ(I) R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.061 wR(F 2) = 0.131 S = 1.02 2457 reflections 138 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.41 e Å−3 Δρmin = −0.28 e Å−3 Absolute structure: Flack (1983 ▶), 961 Friedel pairs Flack parameter: 0.09 (16) Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000365/bq2272sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000365/bq2272Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H13NO3SF(000) = 552
Mr = 263.30Dx = 1.383 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1503 reflections
a = 5.3094 (5) Åθ = 2.5–25.2°
b = 8.5309 (10) ŵ = 0.26 mm−1
c = 27.925 (3) ÅT = 296 K
V = 1264.8 (2) Å3Needle, white
Z = 40.30 × 0.14 × 0.12 mm
Bruker Kappa APEXII CCD diffractometer2457 independent reflections
Radiation source: fine-focus sealed tube1503 reflections with I > 2σ(I)
graphiteRint = 0.060
Detector resolution: 8.00 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = −4→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −9→10
Tmin = 0.961, Tmax = 0.970l = −32→31
7272 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131w = 1/[σ2(Fo2) + (0.0506P)2 + 0.2719P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2457 reflectionsΔρmax = 0.41 e Å−3
138 parametersΔρmin = −0.28 e Å−3
1 restraintAbsolute structure: Flack (1983), 961 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.09 (16)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/UeqOcc. (<1)
S10.5888 (2)1.17782 (15)0.14716 (4)0.0434 (4)
O10.6723 (6)1.2938 (4)0.18015 (10)0.0615 (14)
O20.3371 (4)1.1850 (4)0.12785 (9)0.0549 (13)
O30.7036 (6)0.8660 (4)−0.07098 (11)0.0570 (12)
N10.7813 (6)1.1858 (5)0.10190 (12)0.0427 (14)
C1A0.6261 (14)0.9927 (7)0.1750 (2)0.0500 (19)0.56 (3)
C2A0.7618 (19)0.9727 (8)0.2171 (3)0.0500 (19)0.56 (3)
C3A0.786 (2)0.8243 (10)0.2371 (2)0.0500 (19)0.56 (3)
C4A0.6743 (17)0.6959 (8)0.2150 (2)0.0500 (19)0.56 (3)
C5A0.5386 (12)0.7159 (8)0.1729 (3)0.0500 (19)0.56 (3)
C6A0.5145 (17)0.8643 (9)0.1529 (3)0.0500 (19)0.56 (3)
C70.7490 (7)1.0996 (5)0.05846 (15)0.0353 (16)
C80.5531 (8)1.1329 (5)0.02810 (14)0.0403 (16)
C90.5314 (8)1.0566 (5)−0.01519 (16)0.0413 (17)
C100.7056 (8)0.9465 (6)−0.02856 (16)0.0407 (17)
C110.9050 (9)0.9139 (5)0.00183 (17)0.0490 (17)
C120.9241 (9)0.9870 (6)0.04544 (16)0.0473 (16)
C130.4974 (11)0.8934 (7)−0.10251 (17)0.075 (3)
C3B0.879 (3)0.8430 (11)0.2267 (4)0.054 (3)0.44 (3)
C4B0.726 (2)0.7133 (10)0.2186 (3)0.054 (3)0.44 (3)
C5B0.5220 (14)0.7245 (11)0.1876 (6)0.054 (3)0.44 (3)
C6B0.4708 (16)0.8655 (12)0.1646 (5)0.054 (3)0.44 (3)
C2B0.827 (3)0.9840 (9)0.2037 (5)0.054 (3)0.44 (3)
C1B0.6235 (18)0.9952 (10)0.1726 (3)0.054 (3)0.44 (3)
H6A0.423690.877690.124700.0601*0.56 (3)
H5A0.463900.629980.158120.0601*0.56 (3)
H111.027140.84188−0.007420.0589*
H121.054440.961010.066230.0569*
H13A0.342170.88310−0.085170.1122*
H13B0.501470.81823−0.128090.1122*
H13C0.509670.99726−0.115520.1122*
H80.433981.207590.036800.0480*
H90.397671.08001−0.035470.0494*
H10.930 (4)1.197 (5)0.1105 (13)0.0514*
H2A0.836521.058630.231890.0601*0.56 (3)
H3A0.876720.810920.265320.0601*0.56 (3)
H4A0.690410.596600.228430.0601*0.56 (3)
H2B0.929551.070750.209040.0646*0.44 (3)
H3B1.015050.835490.247420.0646*0.44 (3)
H4B0.760210.618990.234000.0646*0.44 (3)
H5B0.419880.637750.182210.0646*0.44 (3)
H6B0.334380.873010.143840.0646*0.44 (3)
U11U22U33U12U13U23
S10.0335 (6)0.0474 (8)0.0494 (7)0.0026 (6)−0.0036 (5)−0.0007 (7)
O10.060 (2)0.060 (3)0.0646 (19)−0.0021 (18)−0.0064 (16)−0.022 (2)
O20.0254 (16)0.075 (3)0.0642 (18)0.0085 (17)−0.0046 (13)0.004 (2)
O30.056 (2)0.057 (2)0.058 (2)0.0110 (17)0.0010 (17)−0.0093 (18)
N10.0250 (19)0.054 (3)0.049 (2)−0.005 (2)−0.0056 (17)0.005 (2)
C1A0.042 (3)0.056 (4)0.052 (3)−0.004 (2)−0.001 (2)0.014 (2)
C2A0.042 (3)0.056 (4)0.052 (3)−0.004 (2)−0.001 (2)0.014 (2)
C3A0.042 (3)0.056 (4)0.052 (3)−0.004 (2)−0.001 (2)0.014 (2)
C4A0.042 (3)0.056 (4)0.052 (3)−0.004 (2)−0.001 (2)0.014 (2)
C5A0.042 (3)0.056 (4)0.052 (3)−0.004 (2)−0.001 (2)0.014 (2)
C6A0.042 (3)0.056 (4)0.052 (3)−0.004 (2)−0.001 (2)0.014 (2)
C70.025 (2)0.034 (3)0.047 (3)−0.0053 (19)0.005 (2)0.004 (2)
C80.026 (2)0.046 (3)0.049 (3)0.007 (2)−0.003 (2)0.007 (2)
C90.036 (3)0.041 (3)0.047 (3)0.006 (2)−0.003 (2)0.007 (2)
C100.033 (3)0.037 (3)0.052 (3)−0.004 (2)0.002 (2)0.003 (2)
C110.035 (3)0.041 (3)0.071 (3)0.006 (2)0.000 (3)0.005 (3)
C120.028 (2)0.053 (3)0.061 (3)0.003 (2)−0.006 (2)0.010 (3)
C130.088 (5)0.081 (5)0.055 (3)0.018 (3)−0.017 (3)−0.017 (3)
C3B0.055 (4)0.055 (5)0.052 (4)−0.021 (3)−0.010 (3)0.010 (3)
C4B0.055 (4)0.055 (5)0.052 (4)−0.021 (3)−0.010 (3)0.010 (3)
C5B0.055 (4)0.055 (5)0.052 (4)−0.021 (3)−0.010 (3)0.010 (3)
C6B0.055 (4)0.055 (5)0.052 (4)−0.021 (3)−0.010 (3)0.010 (3)
C2B0.055 (4)0.055 (5)0.052 (4)−0.021 (3)−0.010 (3)0.010 (3)
C1B0.055 (4)0.055 (5)0.052 (4)−0.021 (3)−0.010 (3)0.010 (3)
S1—O11.423 (3)C7—C121.385 (6)
S1—O21.442 (2)C8—C91.378 (6)
S1—N11.627 (3)C9—C101.370 (6)
S1—C1A1.771 (6)C10—C111.385 (6)
S1—C1B1.722 (9)C11—C121.372 (7)
O3—C101.369 (6)C2A—H2A0.9300
O3—C131.424 (6)C2B—H2B0.9300
N1—C71.429 (6)C3A—H3A0.9300
N1—H10.83 (2)C3B—H3B0.9300
C1A—C6A1.390 (10)C4A—H4A0.9300
C1A—C2A1.389 (11)C4B—H4B0.9300
C1B—C2B1.390 (18)C5A—H5A0.9300
C1B—C6B1.390 (13)C5B—H5B0.9300
C2A—C3A1.390 (11)C6A—H6A0.9300
C2B—C3B1.391 (14)C6B—H6B0.9300
C3A—C4A1.390 (11)C8—H80.9300
C3B—C4B1.391 (15)C9—H90.9300
C4A—C5A1.389 (10)C11—H110.9300
C4B—C5B1.390 (15)C12—H120.9300
C5A—C6A1.390 (11)C13—H13B0.9600
C5B—C6B1.390 (16)C13—H13C0.9600
C7—C81.372 (6)C13—H13A0.9600
S1···H83.2000C9···H8viii3.0000
O1···C3Ai3.366 (9)C10···H11vi2.8200
O2···C83.045 (5)C11···H11vi2.9700
O2···N1ii3.039 (4)C13···H5Av2.9300
O1···H4Aiii2.9200C13···H92.5100
O1···H2B2.4800H1···O2vii2.22 (2)
O1···H3Aiv2.8400H1···H122.4500
O1···H3Biv2.6400H2A···O12.6200
O1···H2A2.6200H2B···O12.4800
O2···H1ii2.22 (2)H2B···H4Biv2.3300
O2···H6A2.6600H2B···C4Biv2.9800
O2···H82.6000H2B···H3Biv2.5800
O2···H6B2.7000H3A···O1xi2.8400
O3···H5Av2.8000H3B···O1xi2.6400
O3···H6Av2.8200H3B···H2Bxi2.5800
O3···H12vi2.9000H4A···O1xii2.9200
N1···O2vii3.039 (4)H4A···C2Aix3.0300
N1···H9viii2.8000H4B···C2Bxi3.0300
C2A···C4Ai3.547 (12)H4B···H2Bxi2.3300
C3A···O1ix3.366 (9)H5A···O3vi2.8000
C3B···C6Bvii3.594 (18)H5A···C13vi2.9300
C4A···C2Aix3.547 (12)H6A···O3vi2.8200
C5A···C13v3.266 (9)H6A···O22.6600
C6A···C73.540 (9)H6B···H13Bvi2.4500
C6B···C3Bii3.594 (18)H6B···O22.7000
C7···C9viii3.509 (6)H8···S13.2000
C7···C6A3.540 (9)H8···O22.6000
C8···C12ii3.597 (6)H8···C8x3.0400
C8···O23.045 (5)H8···C9x3.0000
C9···C7x3.509 (6)H9···C132.5100
C9···C11ii3.573 (6)H9···H13A2.2000
C10···C11vi3.544 (7)H9···H13C2.4200
C11···C10v3.544 (7)H9···N1x2.8000
C11···C9vii3.573 (6)H9···C7x2.9200
C12···C8vii3.597 (6)H9···C8x3.0600
C13···C5Avi3.266 (9)H11···C11v2.9700
C2A···H4Ai3.0300H11···C10v2.8200
C2B···H4Biv3.0300H12···O3v2.9000
C4A···H13Bv2.9900H12···H12.4500
C4B···H13Bv2.9300H13A···C92.6500
C4B···H2Bxi2.9800H13A···C5Avi3.0500
C5A···H13Av3.0500H13A···H92.2000
C5A···H13Bv2.7700H13B···C4Avi2.9900
C5B···H13Bv3.0600H13B···C6Avi3.1000
C6A···H13Bv3.1000H13B···C4Bvi2.9300
C7···H9viii2.9200H13B···C5Bvi3.0600
C8···H8viii3.0400H13B···H6Bv2.4500
C8···H9viii3.0600H13B···C5Avi2.7700
C9···H13C2.8500H13C···C92.8500
C9···H13A2.6500H13C···H92.4200
O1—S1—O2120.1 (2)C10—C11—C12120.6 (4)
O1—S1—N1106.2 (2)C7—C12—C11119.9 (4)
O1—S1—C1A107.5 (2)C1A—C2A—H2A120.00
O1—S1—C1B109.2 (3)C3A—C2A—H2A120.00
O2—S1—N1106.85 (17)C1B—C2B—H2B120.00
O2—S1—C1A107.8 (3)C3B—C2B—H2B120.00
O2—S1—C1B107.0 (3)C4A—C3A—H3A120.00
N1—S1—C1A107.9 (3)C2A—C3A—H3A120.00
N1—S1—C1B106.9 (3)C4B—C3B—H3B120.00
C10—O3—C13117.3 (4)C2B—C3B—H3B120.00
S1—N1—C7124.2 (3)C3A—C4A—H4A120.00
S1—N1—H1112 (2)C5A—C4A—H4A120.00
C7—N1—H1115 (3)C5B—C4B—H4B120.00
S1—C1A—C2A122.6 (5)C3B—C4B—H4B120.00
S1—C1A—C6A117.4 (5)C6A—C5A—H5A120.00
C2A—C1A—C6A120.0 (6)C4A—C5A—H5A120.00
S1—C1B—C2B113.8 (7)C4B—C5B—H5B120.00
C2B—C1B—C6B120.0 (8)C6B—C5B—H5B120.00
S1—C1B—C6B126.3 (8)C1A—C6A—H6A120.00
C1A—C2A—C3A120.0 (7)C5A—C6A—H6A120.00
C1B—C2B—C3B120.2 (11)C5B—C6B—H6B120.00
C2A—C3A—C4A120.0 (7)C1B—C6B—H6B120.00
C2B—C3B—C4B119.8 (12)C9—C8—H8120.00
C3A—C4A—C5A120.0 (6)C7—C8—H8120.00
C3B—C4B—C5B120.1 (9)C8—C9—H9120.00
C4A—C5A—C6A120.0 (7)C10—C9—H9120.00
C4B—C5B—C6B120.0 (8)C12—C11—H11120.00
C1A—C6A—C5A120.0 (7)C10—C11—H11120.00
C1B—C6B—C5B120.0 (10)C11—C12—H12120.00
N1—C7—C12119.9 (4)C7—C12—H12120.00
N1—C7—C8120.6 (4)O3—C13—H13C109.00
C8—C7—C12119.4 (4)O3—C13—H13B109.00
C7—C8—C9120.5 (4)H13B—C13—H13C109.00
C8—C9—C10120.4 (4)H13A—C13—H13B109.00
O3—C10—C11115.8 (4)H13A—C13—H13C109.00
O3—C10—C9125.1 (4)O3—C13—H13A109.00
C9—C10—C11119.1 (4)
O1—S1—N1—C7−173.2 (3)C2A—C1A—C6A—C5A0.0 (12)
O2—S1—N1—C7−43.9 (4)C1A—C2A—C3A—C4A−0.1 (14)
C1A—S1—N1—C771.8 (4)C2A—C3A—C4A—C5A0.0 (13)
O1—S1—C1A—C2A−11.8 (7)C3A—C4A—C5A—C6A0.0 (12)
O1—S1—C1A—C6A168.6 (6)C4A—C5A—C6A—C1A0.0 (12)
O2—S1—C1A—C2A−142.6 (7)N1—C7—C8—C9175.8 (4)
O2—S1—C1A—C6A37.8 (6)C12—C7—C8—C9−0.7 (6)
N1—S1—C1A—C2A102.3 (7)N1—C7—C12—C11−174.4 (4)
N1—S1—C1A—C6A−77.3 (6)C8—C7—C12—C112.2 (7)
C13—O3—C10—C9−3.3 (7)C7—C8—C9—C10−0.1 (7)
C13—O3—C10—C11178.3 (4)C8—C9—C10—O3−178.9 (4)
S1—N1—C7—C867.4 (5)C8—C9—C10—C11−0.6 (7)
S1—N1—C7—C12−116.2 (4)O3—C10—C11—C12−179.4 (4)
S1—C1A—C2A—C3A−179.6 (7)C9—C10—C11—C122.1 (7)
C6A—C1A—C2A—C3A0.0 (13)C10—C11—C12—C7−2.9 (7)
S1—C1A—C6A—C5A179.6 (6)
Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C7–C12 and C1B–C6B rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O2vii0.83 (2)2.22 (2)3.039 (4)170 (4)
C8—H8···Cg2x0.932.933.613 (5)132
C13—H13B···Cg1vi0.962.983.766 (6)140
C13—H13B···Cg3vi0.962.963.763 (7)143
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C7–C12 and C1B–C6B rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O2i0.83 (2)2.22 (2)3.039 (4)170 (4)
C8—H8⋯Cg2ii0.932.933.613 (5)132
C13—H13B⋯Cg1iii0.962.983.766 (6)140
C13—H13B⋯Cg3iii0.962.963.763 (7)143

Symmetry codes: (i) ; (ii) ; (iii) .

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  4 in total
  1 in total

1.  N,N'-Dibenzyl-N,N'-dimethyl-N''-(methyl-sulfon-yl)phospho-ric triamide.

Authors:  Mehrdad Pourayoubi; Sepideh Sadeghi Seraji; Giuseppe Bruno; Hadi Amiri Rudbari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-07
  1 in total

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