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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2426.
Published online 2009 September 9. doi:  10.1107/S1600536809036010
PMCID: PMC2970392

4-[(E)-(5-Bromo-2-hydroxy­phen­yl)methyl­ideneamino]benzene­sulfonamide

Abstract

In the title compound, C13H11ClN2O3S, the dihedral angle between the benzene rings is 12.26 (33)° and an intra­molecular O—H(...)N hydrogen bond helps to establish the conformation. In the crystal, N—H(...)O and C—H(...)O inter­actions link the mol­ecules.

Related literature

For a related structure and background discussion, see: Chohan et al. (2009 [triangle]). For graph-set theory, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o2426-scheme1.jpg

Experimental

Crystal data

  • C13H11BrN2O3S
  • M r = 355.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2426-efi1.jpg
  • a = 6.1224 (15) Å
  • b = 4.5263 (13) Å
  • c = 23.445 (9) Å
  • β = 94.44 (2)°
  • V = 647.8 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.34 mm−1
  • T = 100 K
  • 0.22 × 0.20 × 0.16 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.482, T max = 0.587
  • 3181 measured reflections
  • 1653 independent reflections
  • 1458 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.087
  • S = 1.00
  • 1653 reflections
  • 188 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.71 e Å−3
  • Δρmin = −1.13 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 279 Friedal pairs
  • Flack parameter: 0.025 (16)

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/S1600536809036010/hb5090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036010/hb5090Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

As part of our ongoing studies of sulfonamides, we now report the structure of the title compound, (I). The crystal structure of (II) 4-{[(E)-(5-chloro-2-hydroxyphenyl) methylidene]amino}benzenesulfonamide (Chohan et al., 2009) 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 (C8—C13) of sulfanilamide are oriented at a dihedral angle of 12.03 (36)°. The Br1 and S1 atoms are at a distance of -0.016 (8) and -0.159 (9) A° from the mean square planes of rings A and B, respectively. There exist two intramolecular H-bonds (Table 1, Fig. 1) forming S(5) and S(6) ring motifs (Bernstein et al., 1995). Three intermolecular H-bondings (Table 1) link the molecules in polymeric nature extending along the b axis (Fig. 2) and forming R33(10) and R21(8) ring motifs.

Experimental

Sulfanilamide (0.344 g, 2 mmol) in ethanol (20 ml) was mixed with 5-bromosalicylaldehyde (0.402 g, 2 mmol) in ethanol (10 ml). The resultant mixture was refluxed for 4 h by monitoring through TLC. During refluxing the solution turned from colorless to orange yellow. After completion of reaction, it was cooled to room temperature, filtered and volume reduced to about one-third using rotary evaporator. It was then allowed to stand for 7 days at room temperature. After which a crystallized product was formed that was filtered, washed with ethanol (2 × 5 ml), dried and recrystallized in a mixture of methanol and ethanol (1:1) to afford shiny orange yellow prisms of (I).

Refinement

The coordinates of H-atoms of the NH2 group were refined. The other H-atoms were positioned geometrically with O—H = 0.82, C—H = 0.93 Å for aromatic 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 radius. The dotted line indicate the intramolecular H-bond.
Fig. 2.
The partial packing of (I) showing how molecules form polymeric chains extending along the crystallographic b axis and ring motifs exist.

Crystal data

C13H11BrN2O3SF(000) = 356
Mr = 355.21Dx = 1.821 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1653 reflections
a = 6.1224 (15) Åθ = 3.3–25.5°
b = 4.5263 (13) ŵ = 3.34 mm1
c = 23.445 (9) ÅT = 100 K
β = 94.44 (2)°Prismatic, yellow
V = 647.8 (3) Å30.22 × 0.20 × 0.16 mm
Z = 2

Data collection

Bruker Kappa APEXII CCD diffractometer1653 independent reflections
Radiation source: fine-focus sealed tube1458 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 7.80 pixels mm-1θmax = 25.5°, θmin = 3.3°
ω scansh = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −2→5
Tmin = 0.482, Tmax = 0.587l = −28→28
3181 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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
1653 reflectionsΔρmax = 0.71 e Å3
188 parametersΔρmin = −1.13 e Å3
1 restraintAbsolute structure: Flack (1983), 279 Friedal pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.025 (16)

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
Br10.22142 (8)1.43584 (16)0.03133 (2)0.0184 (2)
S10.2382 (2)−0.1521 (3)0.42877 (6)0.0131 (4)
O10.8682 (5)0.9320 (15)0.21201 (14)0.0184 (11)
O20.0460 (7)−0.3040 (10)0.40583 (17)0.0175 (12)
O30.4146 (6)−0.3217 (10)0.45633 (17)0.0148 (12)
N10.5538 (8)0.6166 (11)0.2472 (2)0.0141 (16)
N20.1639 (9)0.0737 (13)0.4770 (2)0.0166 (17)
C10.5019 (8)0.947 (2)0.16824 (19)0.0124 (14)
C20.7192 (9)1.0429 (15)0.1723 (2)0.0134 (16)
C30.7829 (9)1.2590 (14)0.1347 (2)0.0148 (17)
C40.6381 (9)1.3763 (12)0.0932 (2)0.0143 (19)
C50.4222 (9)1.2702 (14)0.0883 (2)0.0120 (17)
C60.3552 (10)1.0646 (14)0.1257 (2)0.0149 (17)
C70.4239 (9)0.7346 (14)0.2085 (2)0.0134 (17)
C80.4747 (8)0.4182 (18)0.2878 (2)0.0114 (14)
C90.6126 (9)0.3535 (13)0.3358 (2)0.0147 (19)
C100.5457 (10)0.1737 (14)0.3780 (3)0.0155 (17)
C110.3363 (9)0.0532 (14)0.3724 (2)0.0135 (17)
C120.1995 (9)0.1113 (13)0.3242 (2)0.0134 (17)
C130.2664 (9)0.2936 (14)0.2818 (2)0.0145 (17)
H10.812780.796860.229190.0218*
H30.927111.325190.137720.0176*
H40.682121.523080.068790.0172*
H60.210071.002070.122770.0178*
H70.276230.683910.206070.0155*
H90.752930.433450.339400.0177*
H100.639360.132500.410160.0182*
H120.060760.026600.320240.0159*
H130.173120.333140.249530.0172*
H210.258 (12)0.139 (18)0.493 (3)0.0197*
H220.062 (11)0.200 (17)0.460 (3)0.0197*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0216 (3)0.0200 (3)0.0131 (3)0.0009 (4)−0.0012 (2)0.0024 (3)
S10.0143 (7)0.0109 (8)0.0142 (7)−0.0014 (6)0.0010 (5)0.0006 (5)
O10.0173 (18)0.019 (2)0.0186 (18)−0.009 (3)0.0003 (14)0.010 (3)
O20.017 (2)0.017 (2)0.018 (2)−0.006 (2)−0.0015 (17)0.0027 (19)
O30.014 (2)0.013 (2)0.017 (2)0.0027 (18)−0.0014 (17)0.0053 (17)
N10.013 (2)0.013 (3)0.017 (3)−0.002 (2)0.005 (2)−0.001 (2)
N20.018 (3)0.010 (3)0.022 (3)−0.001 (3)0.003 (2)−0.001 (2)
C10.015 (2)0.010 (3)0.013 (2)0.005 (4)0.0056 (19)−0.006 (4)
C20.017 (3)0.018 (3)0.005 (2)−0.001 (3)0.000 (2)−0.003 (2)
C30.011 (3)0.011 (3)0.023 (3)−0.002 (3)0.006 (2)0.004 (3)
C40.020 (3)0.008 (4)0.016 (3)−0.005 (3)0.009 (2)0.001 (2)
C50.016 (3)0.010 (3)0.010 (3)0.005 (3)0.002 (2)−0.006 (2)
C60.015 (3)0.015 (3)0.015 (3)−0.001 (3)0.003 (2)−0.004 (3)
C70.013 (3)0.008 (3)0.020 (3)−0.004 (3)0.007 (2)−0.002 (3)
C80.017 (2)0.004 (3)0.014 (2)0.002 (3)0.006 (2)0.001 (3)
C90.009 (3)0.010 (4)0.025 (3)−0.002 (2)0.001 (2)−0.002 (2)
C100.017 (3)0.016 (3)0.013 (3)0.001 (3)−0.002 (2)0.003 (3)
C110.017 (3)0.008 (3)0.016 (3)0.001 (3)0.005 (2)0.001 (2)
C120.012 (3)0.014 (3)0.014 (3)−0.004 (3)0.000 (2)−0.001 (3)
C130.016 (3)0.013 (3)0.014 (3)0.002 (3)−0.002 (2)−0.002 (3)

Geometric parameters (Å, °)

Br1—C51.898 (5)C4—C51.403 (8)
S1—O21.431 (5)C5—C61.363 (8)
S1—O31.437 (4)C8—C131.392 (8)
S1—N21.616 (5)C8—C91.385 (7)
S1—C111.759 (6)C9—C101.368 (9)
O1—C21.349 (7)C10—C111.390 (8)
O1—H10.8200C11—C121.379 (7)
N1—C81.421 (8)C12—C131.378 (8)
N1—C71.276 (7)C3—H30.9300
N2—H210.73 (8)C4—H40.9300
N2—H220.92 (7)C6—H60.9300
C1—C71.454 (9)C7—H70.9300
C1—C61.395 (8)C9—H90.9300
C1—C21.396 (8)C10—H100.9300
C2—C31.393 (8)C12—H120.9300
C3—C41.372 (7)C13—H130.9300
O2—S1—O3118.7 (3)C9—C8—C13119.5 (5)
O2—S1—N2107.4 (3)N1—C8—C9117.4 (5)
O2—S1—C11106.9 (3)C8—C9—C10121.0 (5)
O3—S1—N2105.4 (3)C9—C10—C11119.4 (6)
O3—S1—C11109.4 (3)S1—C11—C10120.2 (4)
N2—S1—C11108.8 (3)C10—C11—C12120.0 (5)
C2—O1—H1109.00S1—C11—C12119.7 (4)
C7—N1—C8121.0 (5)C11—C12—C13120.6 (5)
S1—N2—H22108 (5)C8—C13—C12119.4 (5)
S1—N2—H21111 (6)C2—C3—H3119.00
H21—N2—H22117 (8)C4—C3—H3119.00
C2—C1—C6119.2 (6)C3—C4—H4121.00
C2—C1—C7121.4 (5)C5—C4—H4121.00
C6—C1—C7119.4 (5)C1—C6—H6120.00
O1—C2—C1121.4 (5)C5—C6—H6120.00
C1—C2—C3119.2 (5)N1—C7—H7119.00
O1—C2—C3119.4 (5)C1—C7—H7119.00
C2—C3—C4121.6 (5)C8—C9—H9119.00
C3—C4—C5118.6 (5)C10—C9—H9119.00
C4—C5—C6120.6 (5)C9—C10—H10120.00
Br1—C5—C4118.5 (4)C11—C10—H10120.00
Br1—C5—C6120.8 (4)C11—C12—H12120.00
C1—C6—C5120.7 (6)C13—C12—H12120.00
N1—C7—C1121.4 (5)C8—C13—H13120.00
N1—C8—C13123.1 (5)C12—C13—H13120.00
O2—S1—C11—C10−166.2 (5)O1—C2—C3—C4179.3 (5)
O2—S1—C11—C1218.2 (6)C1—C2—C3—C4−1.1 (9)
O3—S1—C11—C10−36.6 (6)C2—C3—C4—C5−1.2 (8)
O3—S1—C11—C12147.9 (5)C3—C4—C5—Br1179.4 (4)
N2—S1—C11—C1078.1 (6)C3—C4—C5—C63.0 (8)
N2—S1—C11—C12−97.5 (5)Br1—C5—C6—C1−178.8 (5)
C8—N1—C7—C1177.5 (6)C4—C5—C6—C1−2.5 (9)
C7—N1—C8—C9−165.3 (6)N1—C8—C9—C10177.4 (6)
C7—N1—C8—C1313.4 (10)C13—C8—C9—C10−1.3 (10)
C6—C1—C2—O1−178.8 (6)N1—C8—C13—C12−177.7 (6)
C6—C1—C2—C31.6 (10)C9—C8—C13—C121.0 (9)
C7—C1—C2—O13.2 (10)C8—C9—C10—C110.3 (9)
C7—C1—C2—C3−176.4 (6)C9—C10—C11—S1−174.5 (5)
C2—C1—C6—C50.2 (10)C9—C10—C11—C121.1 (9)
C7—C1—C6—C5178.2 (6)S1—C11—C12—C13174.2 (5)
C2—C1—C7—N1−3.7 (10)C10—C11—C12—C13−1.4 (9)
C6—C1—C7—N1178.3 (6)C11—C12—C13—C80.4 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.583 (7)146
N2—H21···O3i0.73 (8)2.26 (7)2.950 (7)160 (8)
N2—H22···O2ii0.92 (7)2.58 (8)3.325 (7)139 (6)
C9—H9···O2iii0.932.573.386 (7)146

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5090).

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, o57. [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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