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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 10| October 2009| Page o2426
doi:10.1107/S1600536809036010

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

Zahid H. Chohan,a Hazoor A. Shada and M. Nawaz Tahirb*

aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 6 September 2009; accepted 6 September 2009; online 9 September 2009)

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[Chohan, Z. H., Shad, H. A. & Tahir, M. N. (2009). Acta Cryst. E65, o57.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11BrN2O3S

  • Mr = 355.21

  • Monoclinic, P 21

  • 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[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.482, Tmax = 0.587

  • 3181 measured reflections

  • 1653 independent reflections

  • 1458 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 279 Friedal pairs

  • Flack parameter: 0.025 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.86 2.583 (7) 146
N2—H21⋯O3i 0.73 (8) 2.26 (7) 2.950 (7) 160 (8)
N2—H22⋯O2ii 0.92 (7) 2.58 (8) 3.325 (7) 139 (6)
C9—H9⋯O2iii 0.93 2.57 3.386 (7) 146
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) x, y+1, z; (iii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036010/hb5090sup1.cif

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

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. The partial packing of (I) showing how molecules form polymeric chains extending along the crystallographic b axis and ring motifs exist.
4-[(E)-(5-Bromo-2-hydroxyphenyl)methylideneamino]benzenesulfonamide top
Crystal data top
C13H11BrN2O3SF(000) = 356
Mr = 355.21Dx = 1.821 Mg m−3
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 mm−1
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 top
Bruker Kappa APEXII CCD
diffractometer		1653 independent reflections
Radiation source: fine-focus sealed tube1458 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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) = 0.087 w = 1/[σ2(Fo2) + (0.0554P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
1653 reflectionsΔρmax = 0.71 e Å−3
188 parametersΔρmin = −1.13 e Å−3
1 restraintAbsolute structure: Flack (1983), 279 Friedal pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.025 (16)
Crystal data top
C13H11BrN2O3SV = 647.8 (3) Å3
Mr = 355.21Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.1224 (15) ŵ = 3.34 mm−1
b = 4.5263 (13) ÅT = 100 K
c = 23.445 (9) Å0.22 × 0.20 × 0.16 mm
β = 94.44 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		1653 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1458 reflections with I > 2σ(I)
Tmin = 0.482, Tmax = 0.587Rint = 0.042
3181 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087Δρmax = 0.71 e Å−3
S = 1.00Δρmin = −1.13 e Å−3
1653 reflectionsAbsolute structure: Flack (1983), 279 Friedal pairs
188 parametersAbsolute structure parameter: 0.025 (16)
1 restraint
Special details top

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) top
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC13H11BrN2O3S
Mr355.21
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)6.1224 (15), 4.5263 (13), 23.445 (9)
β (°) 94.44 (2)
V (Å3)647.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)3.34
Crystal size (mm)0.22 × 0.20 × 0.16
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.482, 0.587
No. of measured, independent and
observed [I > 2σ(I)] reflections		3181, 1653, 1458
Rint0.042
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.087, 1.00
No. of reflections1653
No. of parameters188
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.71, −1.13
Absolute structureFlack (1983), 279 Friedal pairs
Absolute structure parameter0.025 (16)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
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.
 

Acknowledgements

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).

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 10| October 2009| Page o2426
doi:10.1107/S1600536809036010
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