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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2450.
Published online 2009 September 12. doi:  10.1107/S1600536809036083
PMCID: PMC2970355

4-{2-[(5-Bromo-2-hydroxy­benzyl­idene)amino]eth­yl}benzene­sulfonamide

Abstract

In the title compound, C15H15BrN2O3S, the dihedral angle between the benzene rings is 6.1 (2)° and an intra­molecular O—H(...)N hydrogen bond helps to establish the conformation. In the crystal structure, the mol­ecules are linked by way of N—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For related structures, see: Chohan et al. (2008 [triangle], 2009 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o2450-scheme1.jpg

Experimental

Crystal data

  • C15H15BrN2O3S
  • M r = 383.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2450-efi1.jpg
  • a = 50.544 (6) Å
  • b = 6.3146 (10) Å
  • c = 4.8625 (5) Å
  • V = 1551.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.80 mm−1
  • T = 296 K
  • 0.28 × 0.14 × 0.12 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.633, T max = 0.714
  • 8263 measured reflections
  • 2844 independent reflections
  • 2523 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.100
  • S = 1.12
  • 2844 reflections
  • 213 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.79 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1212 Friedel pairs
  • Flack parameter: 0.050 (15)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036083/hb5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036083/hb5091Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HAS greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042-160410-PS2-117).

supplementary crystallographic information

Comment

As part of our ongoing studies of sulfonamide derivatives (Chohan et al. 2009), we now report the preparation and crystal structure of title compound (I), (Fig. 1).

The crystal structure of (II) 4-{2-[(5-chloro-2 hydroxybenzylidene)amino]ethyl} -benzenesulfonamide (Chohan et al., 2008) has been reported which differs from (I) due to chloro substitution instead of bromo.

In (I), the benzene rings A (C1–C6) of 5-bromosalicylaldehyde and B (C10–C15) of sulfanilamide moiety are oriented at a dihedral angle of 6.1 (3)° whereas its value as observed in (II) is 23.95 (18)°. The Br1 and S1 atoms are at a distance of -0.024 (7) and -0.167 (6) Å from the mean square planes of rings A and B, respectively. There exist two intramolecular H-bondings (Table 1, Fig. 1) forming S(5) and S(6) ring motifs (Bernstein et al., 1995). Two intermolecular H-bondings (Table 1, Fig. 2) link the molecules in infinite one dimensional polymeric network extending along the c axis.

Experimental

An ethanol solution (20 ml) of 4-(2-aminoethyl) benzene sulfonamide (0.4005 g, 2 mmol) was added to an ethanol solution (10 ml) of 5-bromosalicylaldehyde (0.402 g, 2 mmol). The reaction mixture was refluxed for 3 h. The colour of the solution gradually changed from colourless to greenish yellow. The solution was cooled to room temperature, filtered and the volume was reduced to about one-third on the rotary evaporator. The resulting mixture was allowed to stand for 10 days, after which bright yellow needles of (I) were obtained.

Refinement

The coordinates of H atoms of NH2 group were refined. The other H atoms were positioned geometrically with O—H = 0.82, C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, N, O), where x = 1.2 for all H atoms.

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown by small circles of arbitrary radii. The dotted line indicate the intramolecular H-bond.
Fig. 2.
The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains.

Crystal data

C15H15BrN2O3SF(000) = 776
Mr = 383.26Dx = 1.640 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2932 reflections
a = 50.544 (6) Åθ = 2.4–28.3°
b = 6.3146 (10) ŵ = 2.80 mm1
c = 4.8625 (5) ÅT = 296 K
V = 1551.9 (3) Å3Needle, yellow
Z = 40.28 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer2844 independent reflections
Radiation source: fine-focus sealed tube2523 reflections with I > 2σ(I)
graphiteRint = 0.035
Detector resolution: 7.80 pixels mm-1θmax = 25.5°, θmin = 2.4°
ω scansh = −52→60
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −7→6
Tmin = 0.633, Tmax = 0.714l = −5→5
8263 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100w = 1/[σ2(Fo2) + 2.7358P] where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
2844 reflectionsΔρmax = 0.41 e Å3
213 parametersΔρmin = −0.79 e Å3
1 restraintAbsolute structure: Flack (1983), 1212 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.050 (15)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.24179 (1)0.37198 (12)1.16449 (17)0.0633 (2)
S10.03204 (2)−0.2434 (2)−0.5033 (3)0.0276 (3)
O10.15029 (7)0.8114 (6)0.6129 (10)0.0543 (16)
O20.04542 (7)−0.4313 (6)−0.5921 (8)0.0460 (12)
O30.02060 (7)−0.1032 (6)−0.7008 (7)0.0398 (11)
N10.14244 (8)0.4653 (8)0.3341 (10)0.0420 (16)
N20.00760 (8)−0.3200 (7)−0.3108 (12)0.0367 (14)
C10.17777 (8)0.5013 (8)0.6554 (13)0.0330 (14)
C20.17084 (9)0.7071 (9)0.7344 (10)0.0360 (17)
C30.18524 (10)0.8111 (9)0.9375 (12)0.0437 (19)
C40.20599 (10)0.7116 (9)1.0649 (10)0.0403 (19)
C50.21316 (9)0.5108 (9)0.9871 (12)0.0373 (16)
C60.19906 (10)0.4058 (9)0.7859 (11)0.0397 (17)
C70.16276 (10)0.3869 (9)0.4471 (11)0.0390 (17)
C80.12783 (10)0.3344 (9)0.1349 (13)0.0463 (19)
C90.10328 (11)0.2403 (10)0.2692 (11)0.0450 (19)
C100.08639 (10)0.1205 (9)0.0700 (9)0.0330 (16)
C110.09253 (10)−0.0829 (9)−0.0103 (12)0.0420 (19)
C120.07651 (10)−0.1935 (8)−0.1920 (12)0.0380 (17)
C130.05431 (8)−0.0959 (7)−0.2953 (9)0.0263 (16)
C140.04792 (10)0.1065 (8)−0.2252 (10)0.0323 (17)
C150.06412 (10)0.2172 (9)−0.0426 (12)0.0403 (17)
H1O0.142590.731000.507320.0815*
H2A−0.0025 (11)−0.224 (8)−0.292 (14)0.0439*
H2B0.0123 (10)−0.405 (9)−0.181 (13)0.0439*
H30.180770.948750.986950.0522*
H40.215220.780301.204230.0481*
H60.203920.268840.737030.042 (16)*
H70.168280.252070.395640.06 (2)*
H8A0.139160.221250.068780.0554*
H8B0.122680.42041−0.021470.0554*
H9A0.108680.145940.416240.0540*
H9B0.092910.353590.350060.0540*
H110.10770−0.147230.058520.06 (2)*
H120.08071−0.33135−0.243120.030 (14)*
H140.032910.17034−0.298200.040 (14)*
H150.060030.356230.004080.030 (13)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0515 (3)0.0879 (5)0.0505 (3)0.0203 (3)−0.0093 (4)−0.0043 (4)
S10.0311 (6)0.0282 (6)0.0234 (5)−0.0029 (5)0.0027 (5)−0.0059 (5)
O10.045 (2)0.047 (3)0.071 (3)0.0065 (19)−0.013 (2)−0.008 (2)
O20.047 (2)0.036 (2)0.055 (2)0.0026 (18)0.0051 (19)−0.0254 (19)
O30.047 (2)0.042 (2)0.0305 (18)−0.0067 (19)−0.0041 (16)0.0036 (17)
N10.030 (2)0.052 (3)0.044 (3)−0.010 (2)−0.001 (2)−0.009 (2)
N20.040 (2)0.036 (3)0.034 (2)−0.0072 (19)0.005 (3)0.002 (2)
C10.028 (2)0.034 (3)0.037 (2)−0.007 (2)0.010 (3)−0.009 (3)
C20.028 (3)0.037 (3)0.043 (3)−0.004 (2)0.008 (2)−0.005 (2)
C30.042 (3)0.036 (3)0.053 (4)−0.002 (2)−0.002 (3)−0.008 (3)
C40.040 (3)0.046 (4)0.035 (3)−0.011 (3)0.004 (2)−0.009 (2)
C50.025 (2)0.052 (3)0.035 (3)0.003 (2)0.008 (2)0.003 (3)
C60.038 (3)0.037 (3)0.044 (3)−0.003 (3)0.008 (2)−0.008 (3)
C70.036 (3)0.040 (3)0.041 (3)−0.006 (2)0.007 (2)−0.008 (3)
C80.042 (3)0.057 (4)0.040 (3)−0.013 (3)−0.011 (3)−0.011 (3)
C90.046 (3)0.051 (4)0.038 (3)−0.013 (3)−0.005 (2)−0.007 (3)
C100.031 (2)0.041 (3)0.027 (3)−0.015 (2)0.0053 (19)−0.004 (2)
C110.034 (3)0.047 (4)0.045 (3)0.003 (2)−0.010 (3)−0.004 (3)
C120.042 (3)0.025 (3)0.047 (3)0.004 (2)−0.007 (3)−0.009 (3)
C130.031 (2)0.028 (3)0.020 (3)−0.0034 (19)0.004 (2)−0.003 (2)
C140.030 (3)0.028 (3)0.039 (3)−0.002 (2)−0.002 (2)−0.002 (2)
C150.045 (3)0.034 (3)0.042 (3)−0.004 (2)0.005 (3)−0.011 (3)

Geometric parameters (Å, °)

Br1—C51.899 (5)C9—C101.496 (8)
S1—O21.432 (4)C10—C151.393 (7)
S1—O31.428 (4)C10—C111.378 (8)
S1—N21.624 (5)C11—C121.387 (8)
S1—C131.777 (4)C12—C131.375 (7)
O1—C21.364 (6)C13—C141.362 (7)
O1—H1O0.8200C14—C151.396 (7)
N1—C71.266 (7)C3—H30.9300
N1—C81.472 (8)C4—H40.9300
N2—H2A0.80 (5)C6—H60.9300
N2—H2B0.86 (6)C7—H70.9300
C1—C71.457 (8)C8—H8A0.9700
C1—C21.400 (8)C8—H8B0.9700
C1—C61.387 (7)C9—H9A0.9700
C2—C31.392 (7)C9—H9B0.9700
C3—C41.371 (7)C11—H110.9300
C4—C51.372 (8)C12—H120.9300
C5—C61.380 (8)C14—H140.9300
C8—C91.523 (8)C15—H150.9300
Br1···C6i3.720 (5)C7···C5vi3.479 (7)
Br1···C4ii3.433 (5)C8···C1vi3.594 (8)
Br1···C5ii3.584 (5)C13···O3i3.356 (6)
Br1···H4iii3.1700C14···O3i3.188 (6)
O1···N12.602 (6)C15···O2x3.259 (7)
O2···C15iv3.259 (7)C15···O3i3.420 (7)
O3···N2v3.076 (6)C7···H1O2.4200
O3···C14vi3.188 (6)C11···H8A3.0600
O3···C15vi3.420 (7)H1O···N11.8800
O3···C13vi3.356 (6)H1O···C72.4200
O2···H122.5400H2A···O3vii2.30 (5)
O2···H15iv2.4900H2B···N2xi2.70 (6)
O2···H9Biv2.7700H4···Br1xii3.1700
O3···H142.6800H6···H72.4500
O3···H2Av2.30 (5)H7···H62.4500
O3···H14v2.7800H7···H8A2.1700
N1···O12.602 (6)H8A···C113.0600
N2···O3vii3.076 (6)H8A···H72.1700
N1···H1O1.8800H9A···H112.5400
N2···H2Bviii2.70 (6)H9B···O2x2.7700
C1···C4vi3.470 (8)H9B···H152.3600
C1···C8i3.594 (8)H11···H9A2.5400
C4···C1i3.470 (8)H12···O22.5400
C4···C7i3.526 (8)H12···H15xiii2.5400
C4···Br1ix3.433 (5)H14···O32.6800
C5···C7i3.479 (7)H14···O3vii2.7800
C5···Br1ix3.584 (5)H15···O2x2.4900
C6···Br1vi3.720 (5)H15···H9B2.3600
C7···C4vi3.526 (8)H15···H12xiv2.5400
O2—S1—O3120.1 (2)S1—C13—C12119.3 (4)
O2—S1—N2106.6 (2)C12—C13—C14121.5 (4)
O2—S1—C13107.9 (2)S1—C13—C14119.0 (3)
O3—S1—N2105.3 (2)C13—C14—C15119.4 (5)
O3—S1—C13108.3 (2)C10—C15—C14120.3 (5)
N2—S1—C13108.1 (2)C2—C3—H3120.00
C2—O1—H1O109.00C4—C3—H3120.00
C7—N1—C8118.2 (5)C3—C4—H4120.00
S1—N2—H2A109 (4)C5—C4—H4120.00
S1—N2—H2B114 (3)C1—C6—H6119.00
H2A—N2—H2B124 (6)C5—C6—H6119.00
C2—C1—C7121.4 (4)N1—C7—H7119.00
C6—C1—C7120.4 (5)C1—C7—H7119.00
C2—C1—C6118.2 (5)N1—C8—H8A110.00
O1—C2—C1121.3 (5)N1—C8—H8B110.00
O1—C2—C3118.5 (5)C9—C8—H8A110.00
C1—C2—C3120.1 (5)C9—C8—H8B110.00
C2—C3—C4120.3 (5)H8A—C8—H8B108.00
C3—C4—C5120.1 (5)C8—C9—H9A109.00
Br1—C5—C4120.2 (4)C8—C9—H9B109.00
Br1—C5—C6119.6 (4)C10—C9—H9A109.00
C4—C5—C6120.2 (5)C10—C9—H9B109.00
C1—C6—C5121.1 (5)H9A—C9—H9B108.00
N1—C7—C1122.0 (5)C10—C11—H11119.00
N1—C8—C9110.2 (5)C12—C11—H11119.00
C8—C9—C10112.6 (4)C11—C12—H12121.00
C9—C10—C15119.6 (5)C13—C12—H12121.00
C11—C10—C15118.6 (5)C13—C14—H14120.00
C9—C10—C11121.8 (5)C15—C14—H14120.00
C10—C11—C12121.2 (5)C10—C15—H15120.00
C11—C12—C13118.9 (5)C14—C15—H15120.00
O2—S1—C13—C12−16.3 (5)C2—C3—C4—C51.9 (8)
O2—S1—C13—C14168.7 (4)C3—C4—C5—Br1−179.7 (4)
O3—S1—C13—C12−147.7 (4)C3—C4—C5—C6−1.9 (8)
O3—S1—C13—C1437.2 (4)Br1—C5—C6—C1178.9 (4)
N2—S1—C13—C1298.7 (4)C4—C5—C6—C11.1 (8)
N2—S1—C13—C14−76.4 (4)N1—C8—C9—C10175.1 (5)
C8—N1—C7—C1−177.3 (5)C8—C9—C10—C1179.5 (7)
C7—N1—C8—C9101.1 (6)C8—C9—C10—C15−99.3 (6)
C6—C1—C2—O1179.3 (5)C9—C10—C11—C12179.0 (5)
C6—C1—C2—C30.4 (8)C15—C10—C11—C12−2.2 (8)
C7—C1—C2—O1−2.2 (8)C9—C10—C15—C14−179.0 (5)
C7—C1—C2—C3178.8 (5)C11—C10—C15—C142.3 (8)
C2—C1—C6—C5−0.4 (8)C10—C11—C12—C130.8 (8)
C7—C1—C6—C5−178.8 (5)C11—C12—C13—S1−174.3 (4)
C2—C1—C7—N1−2.0 (8)C11—C12—C13—C140.6 (8)
C6—C1—C7—N1176.4 (5)S1—C13—C14—C15174.4 (4)
O1—C2—C3—C4179.9 (5)C12—C13—C14—C15−0.5 (7)
C1—C2—C3—C4−1.2 (8)C13—C14—C15—C10−1.0 (8)

Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y−1/2, z+1/2; (iii) −x+1/2, y−1/2, z−1/2; (iv) x, y−1, z−1; (v) −x, −y, z−1/2; (vi) x, y, z−1; (vii) −x, −y, z+1/2; (viii) −x, −y−1, z−1/2; (ix) −x+1/2, y+1/2, z−1/2; (x) x, y+1, z+1; (xi) −x, −y−1, z+1/2; (xii) −x+1/2, y+1/2, z+1/2; (xiii) x, y−1, z; (xiv) x, y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.821.882.602 (6)147
N2—H2A···O3vii0.80 (5)2.30 (5)3.076 (6)163 (5)
C15—H15···O2x0.932.493.259 (7)140

Symmetry codes: (vii) −x, −y, z+1/2; (x) x, y+1, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5091).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chohan, Z. H., Shad, H. A. & Tahir, M. N. (2009). Acta Cryst. E65, o2426. [PMC free article] [PubMed]
  • Chohan, Z. H., Shad, H. A., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o725. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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