organic compounds
4-[(5-Bromo-2-hydroxybenzylidene)amino]-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]phenolate [0.61 (7)/0.39 (7)]
aDepartment of Chemistry, Bahauddin Zakariya University, Multan-60800, Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
The title compound, 0.61C19H17BrN4O3S·0.39C19H17BrN4O3S, is a Schiff base derived from 5-bromosalicylaldehyde and 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide(sulfamethazine) and is isostructural with its chloro analogue. The geometry of the title molecule points to the enol (OH—C=C—C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intramolecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O−—C=C—C=NH+) form in the crystal. of the occupancies of these H atoms gave a 0.61 (7):0.39 (7) ratio of the enolic and zwitterionic forms. The two benzene rings within the molecule are nearly coplanar and the central benzene ring forms a dihedral angle of 84.1 (1)° with the pyrimidine fragment. An intermolecular N—H⋯O hydrogen bond links molecules into chains extended along the a axis and a C—H⋯O link is also present. The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7).
Related literature
For the crystal structures of similar sulphonamides, see: Chohan et al. (2008a,b); Shad et al. (2008); Tahir et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); 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, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON.
Supporting information
10.1107/S1600536808041214/gk2160sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808041214/gk2160Isup2.hkl
Sulfamethazine (0.5566 g, 2 mmol) in ethanol (15 ml) was reacted with ethanolic (10 ml) solution of 5-bromosalicylaldehyde (0.4020 g, 2 mmol). The mixture was refluxed for 3 h. The colour of the solution gradually changed from colourless to orange-red. The solution was then cooled to room temperature, filtered and volume reduced to about one-third on rotary evaporator. After 12 days crystals of the title compound were obtained.
The positions of H-atoms attached to O1 and N1 were determined from the difference Fourier synthesis and in the
these atoms were constrained to ride on their parent atoms. Their occupancy factors were allowed to refine with the the sum of the occupancy factors constrained to 1.00. Remaining H-atoms were positioned geometrically, with C—H = 0.93-0.96 Å. The Uiso(H) = xUeq(C, N, O), where x = 1.5 for methyl H, H1N, H1O and x = 1.2 for all other H atoms. The H-atoms of one of the methyl groups are disordered over two sites with occupancy ratio of 72:28.Data collection: APEX2 (Bruker, 2007); cell
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, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)..0.61C19H17BrN4O3S·0.39C19H17BrN4O3S | Dx = 1.579 Mg m−3 |
Mr = 461.34 | Melting point: 497 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3428 reflections |
a = 11.7919 (9) Å | θ = 2.4–25.0° |
b = 13.9965 (8) Å | µ = 2.26 mm−1 |
c = 23.5117 (17) Å | T = 296 K |
V = 3880.5 (5) Å3 | Prismatic, red |
Z = 8 | 0.20 × 0.16 × 0.14 mm |
F(000) = 1872 |
Bruker KAPPA APEXII CCD diffractometer | 3428 independent reflections |
Radiation source: fine-focus sealed tube | 1961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
Detector resolution: 7.9 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −16→16 |
Tmin = 0.650, Tmax = 0.725 | l = −27→26 |
19597 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.057P)2 + 2.1678P] where P = (Fo2 + 2Fc2)/3 |
3428 reflections | (Δ/σ)max = 0.001 |
257 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
0.61C19H17BrN4O3S·0.39C19H17BrN4O3S | V = 3880.5 (5) Å3 |
Mr = 461.34 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.7919 (9) Å | µ = 2.26 mm−1 |
b = 13.9965 (8) Å | T = 296 K |
c = 23.5117 (17) Å | 0.20 × 0.16 × 0.14 mm |
Bruker KAPPA APEXII CCD diffractometer | 3428 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1961 reflections with I > 2σ(I) |
Tmin = 0.650, Tmax = 0.725 | Rint = 0.081 |
19597 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.35 e Å−3 |
3428 reflections | Δρmin = −0.65 e Å−3 |
257 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 | Occ. (<1) | |
Br1 | 1.18229 (5) | 0.76268 (4) | 0.36991 (3) | 0.0824 (3) | |
S1 | 0.40502 (9) | 0.37094 (8) | 0.60341 (5) | 0.0417 (3) | |
O1 | 0.9535 (3) | 0.3837 (2) | 0.39965 (16) | 0.0716 (11) | |
H1O | 0.9124 | 0.3692 | 0.4287 | 0.086* | 0.61 (7) |
N1 | 0.8172 (3) | 0.4593 (3) | 0.46953 (16) | 0.0426 (9) | |
H1N | 0.8601 | 0.3968 | 0.4558 | 0.051* | 0.39 (7) |
O2 | 0.3377 (3) | 0.3110 (2) | 0.56749 (13) | 0.0560 (9) | |
O3 | 0.3565 (2) | 0.4558 (2) | 0.62541 (13) | 0.0511 (8) | |
N2 | 0.4430 (3) | 0.2997 (2) | 0.65478 (15) | 0.0452 (10) | |
H2N | 0.4177 | 0.2421 | 0.6535 | 0.068* | |
N3 | 0.5374 (3) | 0.2497 (3) | 0.73414 (17) | 0.0472 (10) | |
N4 | 0.5447 (3) | 0.4138 (2) | 0.70529 (16) | 0.0458 (9) | |
C1 | 0.9643 (4) | 0.5482 (3) | 0.42496 (19) | 0.0440 (11) | |
C2 | 1.0200 (4) | 0.6363 (3) | 0.4176 (2) | 0.0493 (12) | |
H2 | 0.9966 | 0.6894 | 0.4383 | 0.059* | |
C3 | 1.1079 (4) | 0.6443 (3) | 0.3803 (2) | 0.0538 (13) | |
C4 | 1.1447 (4) | 0.5657 (4) | 0.3499 (2) | 0.0661 (15) | |
H4 | 1.2054 | 0.5716 | 0.3249 | 0.079* | |
C5 | 1.0922 (4) | 0.4790 (4) | 0.3565 (2) | 0.0685 (16) | |
H5 | 1.1168 | 0.4269 | 0.3352 | 0.082* | |
C6 | 1.0036 (4) | 0.4677 (3) | 0.3942 (2) | 0.0532 (13) | |
C7 | 0.8679 (4) | 0.5393 (3) | 0.46274 (19) | 0.0450 (11) | |
H7 | 0.8424 | 0.5927 | 0.4824 | 0.054* | |
C8 | 0.7198 (3) | 0.4440 (3) | 0.50347 (18) | 0.0375 (10) | |
C9 | 0.6759 (4) | 0.3538 (3) | 0.5027 (2) | 0.0538 (13) | |
H9 | 0.7107 | 0.3067 | 0.4809 | 0.065* | |
C10 | 0.5808 (4) | 0.3317 (3) | 0.5338 (2) | 0.0548 (13) | |
H10 | 0.5514 | 0.2701 | 0.5329 | 0.066* | |
C11 | 0.5290 (3) | 0.4005 (3) | 0.56628 (17) | 0.0359 (10) | |
C12 | 0.5738 (4) | 0.4917 (3) | 0.56843 (19) | 0.0430 (11) | |
H12 | 0.5405 | 0.5382 | 0.5912 | 0.052* | |
C13 | 0.6683 (4) | 0.5127 (3) | 0.5365 (2) | 0.0457 (12) | |
H13 | 0.6979 | 0.5743 | 0.5372 | 0.055* | |
C14 | 0.5124 (3) | 0.3231 (3) | 0.70054 (19) | 0.0417 (11) | |
C15 | 0.6020 (4) | 0.2704 (3) | 0.7790 (2) | 0.0523 (13) | |
C16 | 0.6396 (4) | 0.3624 (4) | 0.7881 (2) | 0.0579 (13) | |
H16 | 0.6850 | 0.3764 | 0.8193 | 0.069* | |
C17 | 0.6095 (4) | 0.4328 (3) | 0.7507 (2) | 0.0501 (12) | |
C18 | 0.6482 (5) | 0.5342 (4) | 0.7575 (3) | 0.0784 (17) | |
H18A | 0.6846 | 0.5550 | 0.7231 | 0.118* | |
H18B | 0.7009 | 0.5382 | 0.7885 | 0.118* | |
H18C | 0.5840 | 0.5743 | 0.7652 | 0.118* | |
C19 | 0.6307 (5) | 0.1897 (4) | 0.8188 (2) | 0.0797 (18) | |
H19A | 0.5973 | 0.1316 | 0.8050 | 0.120* | 0.72 (7) |
H19B | 0.6015 | 0.2036 | 0.8560 | 0.120* | 0.72 (7) |
H19C | 0.7115 | 0.1824 | 0.8208 | 0.120* | 0.72 (7) |
H19D | 0.6762 | 0.2134 | 0.8495 | 0.120* | 0.28 (7) |
H19E | 0.6720 | 0.1414 | 0.7985 | 0.120* | 0.28 (7) |
H19F | 0.5620 | 0.1626 | 0.8337 | 0.120* | 0.28 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0841 (5) | 0.0587 (4) | 0.1044 (6) | −0.0198 (3) | 0.0112 (4) | 0.0058 (3) |
S1 | 0.0396 (6) | 0.0417 (6) | 0.0437 (7) | −0.0038 (5) | −0.0033 (5) | 0.0005 (6) |
O1 | 0.086 (3) | 0.0396 (19) | 0.089 (3) | −0.0101 (18) | 0.039 (2) | −0.0107 (19) |
N1 | 0.044 (2) | 0.043 (2) | 0.041 (2) | 0.0041 (18) | 0.0030 (19) | 0.0006 (18) |
O2 | 0.053 (2) | 0.060 (2) | 0.056 (2) | −0.0146 (16) | −0.0152 (17) | −0.0017 (17) |
O3 | 0.0480 (18) | 0.0495 (19) | 0.056 (2) | 0.0038 (15) | 0.0073 (16) | −0.0015 (16) |
N2 | 0.055 (2) | 0.039 (2) | 0.042 (2) | −0.0141 (18) | −0.010 (2) | 0.0017 (18) |
N3 | 0.047 (2) | 0.051 (2) | 0.043 (3) | 0.0018 (18) | −0.003 (2) | 0.000 (2) |
N4 | 0.050 (2) | 0.046 (2) | 0.042 (3) | −0.0097 (18) | 0.001 (2) | −0.0051 (19) |
C1 | 0.042 (3) | 0.049 (3) | 0.041 (3) | 0.005 (2) | −0.006 (2) | 0.000 (2) |
C2 | 0.056 (3) | 0.038 (3) | 0.054 (3) | 0.002 (2) | −0.003 (3) | −0.003 (2) |
C3 | 0.043 (3) | 0.052 (3) | 0.066 (4) | −0.003 (2) | 0.002 (3) | 0.006 (3) |
C4 | 0.053 (3) | 0.060 (3) | 0.086 (4) | 0.002 (3) | 0.028 (3) | −0.002 (3) |
C5 | 0.063 (3) | 0.052 (3) | 0.091 (5) | 0.001 (3) | 0.031 (3) | −0.010 (3) |
C6 | 0.056 (3) | 0.041 (3) | 0.063 (4) | 0.003 (2) | 0.008 (3) | −0.003 (3) |
C7 | 0.051 (3) | 0.041 (3) | 0.044 (3) | 0.010 (2) | 0.000 (2) | −0.002 (2) |
C8 | 0.037 (2) | 0.043 (3) | 0.033 (3) | 0.004 (2) | 0.002 (2) | 0.001 (2) |
C9 | 0.060 (3) | 0.044 (3) | 0.058 (3) | 0.002 (2) | 0.016 (3) | −0.013 (2) |
C10 | 0.059 (3) | 0.038 (3) | 0.067 (4) | −0.006 (2) | 0.011 (3) | −0.011 (2) |
C11 | 0.040 (2) | 0.034 (2) | 0.034 (3) | 0.0019 (19) | −0.004 (2) | −0.0028 (19) |
C12 | 0.050 (3) | 0.039 (3) | 0.040 (3) | 0.005 (2) | 0.008 (2) | −0.007 (2) |
C13 | 0.050 (3) | 0.035 (2) | 0.052 (3) | −0.004 (2) | 0.006 (2) | −0.006 (2) |
C14 | 0.041 (3) | 0.048 (3) | 0.036 (3) | −0.002 (2) | 0.004 (2) | −0.001 (2) |
C15 | 0.054 (3) | 0.057 (3) | 0.046 (3) | 0.016 (3) | 0.007 (3) | −0.003 (3) |
C16 | 0.046 (3) | 0.082 (4) | 0.046 (3) | 0.008 (3) | −0.009 (2) | −0.016 (3) |
C17 | 0.043 (3) | 0.061 (3) | 0.046 (3) | −0.005 (2) | 0.005 (2) | −0.012 (3) |
C18 | 0.085 (4) | 0.070 (4) | 0.081 (5) | −0.031 (3) | −0.002 (3) | −0.020 (3) |
C19 | 0.095 (4) | 0.083 (4) | 0.061 (4) | 0.035 (3) | −0.016 (3) | 0.002 (3) |
Br1—C3 | 1.890 (5) | C7—H7 | 0.9300 |
S1—O3 | 1.416 (3) | C8—C9 | 1.365 (6) |
S1—O2 | 1.431 (3) | C8—C13 | 1.378 (6) |
S1—N2 | 1.629 (4) | C9—C10 | 1.374 (6) |
S1—C11 | 1.753 (4) | C9—H9 | 0.9300 |
O1—C6 | 1.322 (5) | C10—C11 | 1.372 (6) |
O1—H1O | 0.8621 | C10—H10 | 0.9300 |
N1—C7 | 1.279 (5) | C11—C12 | 1.381 (5) |
N1—C8 | 1.414 (5) | C12—C13 | 1.375 (6) |
N1—H1N | 1.0611 | C12—H12 | 0.9300 |
N2—C14 | 1.391 (5) | C13—H13 | 0.9300 |
N2—H2N | 0.8600 | C15—C16 | 1.378 (6) |
N3—C14 | 1.329 (5) | C15—C19 | 1.506 (7) |
N3—C15 | 1.332 (6) | C16—C17 | 1.368 (6) |
N4—C14 | 1.330 (5) | C16—H16 | 0.9300 |
N4—C17 | 1.339 (6) | C17—C18 | 1.499 (6) |
C1—C2 | 1.408 (6) | C18—H18A | 0.9600 |
C1—C6 | 1.416 (6) | C18—H18B | 0.9600 |
C1—C7 | 1.448 (6) | C18—H18C | 0.9600 |
C2—C3 | 1.362 (6) | C19—H19A | 0.9600 |
C2—H2 | 0.9300 | C19—H19B | 0.9600 |
C3—C4 | 1.382 (7) | C19—H19C | 0.9600 |
C4—C5 | 1.371 (6) | C19—H19D | 0.9600 |
C4—H4 | 0.9300 | C19—H19E | 0.9600 |
C5—C6 | 1.380 (7) | C19—H19F | 0.9600 |
C5—H5 | 0.9300 | ||
O3—S1—O2 | 118.9 (2) | C11—C10—C9 | 120.1 (4) |
O3—S1—N2 | 110.7 (2) | C11—C10—H10 | 120.0 |
O2—S1—N2 | 103.37 (18) | C9—C10—H10 | 120.0 |
O3—S1—C11 | 108.73 (19) | C10—C11—C12 | 119.9 (4) |
O2—S1—C11 | 107.90 (19) | C10—C11—S1 | 118.8 (3) |
N2—S1—C11 | 106.54 (18) | C12—C11—S1 | 121.3 (3) |
C6—O1—H1O | 122.5 | C13—C12—C11 | 119.2 (4) |
C7—N1—C8 | 125.7 (4) | C13—C12—H12 | 120.4 |
C7—N1—H1N | 117.4 | C11—C12—H12 | 120.4 |
C8—N1—H1N | 115.7 | C12—C13—C8 | 121.0 (4) |
C14—N2—S1 | 126.3 (3) | C12—C13—H13 | 119.5 |
C14—N2—H2N | 116.9 | C8—C13—H13 | 119.5 |
S1—N2—H2N | 116.9 | N3—C14—N4 | 128.6 (4) |
C14—N3—C15 | 115.4 (4) | N3—C14—N2 | 114.1 (4) |
C14—N4—C17 | 114.8 (4) | N4—C14—N2 | 117.2 (4) |
C2—C1—C6 | 118.8 (4) | N3—C15—C16 | 120.7 (5) |
C2—C1—C7 | 121.1 (4) | N3—C15—C19 | 117.2 (5) |
C6—C1—C7 | 120.1 (4) | C16—C15—C19 | 122.2 (5) |
C3—C2—C1 | 120.4 (4) | C17—C16—C15 | 119.3 (5) |
C3—C2—H2 | 119.8 | C17—C16—H16 | 120.3 |
C1—C2—H2 | 119.8 | C15—C16—H16 | 120.3 |
C2—C3—C4 | 120.4 (4) | N4—C17—C16 | 121.1 (4) |
C2—C3—Br1 | 120.6 (4) | N4—C17—C18 | 116.6 (5) |
C4—C3—Br1 | 119.0 (4) | C16—C17—C18 | 122.3 (5) |
C5—C4—C3 | 120.3 (5) | C17—C18—H18A | 109.5 |
C5—C4—H4 | 119.8 | C17—C18—H18B | 109.5 |
C3—C4—H4 | 119.8 | H18A—C18—H18B | 109.5 |
C4—C5—C6 | 121.1 (5) | C17—C18—H18C | 109.5 |
C4—C5—H5 | 119.5 | H18A—C18—H18C | 109.5 |
C6—C5—H5 | 119.5 | H18B—C18—H18C | 109.5 |
O1—C6—C5 | 120.2 (4) | C15—C19—H19A | 109.5 |
O1—C6—C1 | 120.8 (4) | C15—C19—H19B | 109.5 |
C5—C6—C1 | 119.0 (4) | H19A—C19—H19B | 109.5 |
N1—C7—C1 | 121.3 (4) | C15—C19—H19C | 109.5 |
N1—C7—H7 | 119.4 | H19A—C19—H19C | 109.5 |
C1—C7—H7 | 119.4 | H19B—C19—H19C | 109.5 |
C9—C8—C13 | 119.1 (4) | C15—C19—H19D | 109.5 |
C9—C8—N1 | 116.2 (4) | C15—C19—H19E | 109.5 |
C13—C8—N1 | 124.7 (4) | H19D—C19—H19E | 109.5 |
C8—C9—C10 | 120.7 (4) | C15—C19—H19F | 109.5 |
C8—C9—H9 | 119.6 | H19D—C19—H19F | 109.5 |
C10—C9—H9 | 119.6 | H19E—C19—H19F | 109.5 |
O3—S1—N2—C14 | −53.3 (4) | O3—S1—C11—C10 | −169.9 (4) |
O2—S1—N2—C14 | 178.3 (4) | O2—S1—C11—C10 | −39.7 (4) |
C11—S1—N2—C14 | 64.7 (4) | N2—S1—C11—C10 | 70.8 (4) |
C6—C1—C2—C3 | 1.9 (7) | O3—S1—C11—C12 | 9.0 (4) |
C7—C1—C2—C3 | −177.5 (4) | O2—S1—C11—C12 | 139.2 (3) |
C1—C2—C3—C4 | −1.1 (7) | N2—S1—C11—C12 | −110.4 (4) |
C1—C2—C3—Br1 | 179.6 (3) | C10—C11—C12—C13 | 1.9 (7) |
C2—C3—C4—C5 | 0.8 (8) | S1—C11—C12—C13 | −177.0 (3) |
Br1—C3—C4—C5 | −179.9 (4) | C11—C12—C13—C8 | −1.3 (7) |
C3—C4—C5—C6 | −1.4 (9) | C9—C8—C13—C12 | −0.1 (7) |
C4—C5—C6—O1 | 179.4 (5) | N1—C8—C13—C12 | −179.8 (4) |
C4—C5—C6—C1 | 2.2 (8) | C15—N3—C14—N4 | 1.1 (7) |
C2—C1—C6—O1 | −179.6 (4) | C15—N3—C14—N2 | −178.7 (4) |
C7—C1—C6—O1 | −0.2 (7) | C17—N4—C14—N3 | −1.1 (7) |
C2—C1—C6—C5 | −2.4 (7) | C17—N4—C14—N2 | 178.7 (4) |
C7—C1—C6—C5 | 177.0 (5) | S1—N2—C14—N3 | −175.0 (3) |
C8—N1—C7—C1 | −177.3 (4) | S1—N2—C14—N4 | 5.2 (6) |
C2—C1—C7—N1 | 180.0 (4) | C14—N3—C15—C16 | −0.7 (6) |
C6—C1—C7—N1 | 0.6 (7) | C14—N3—C15—C19 | 179.0 (4) |
C7—N1—C8—C9 | 177.0 (4) | N3—C15—C16—C17 | 0.4 (7) |
C7—N1—C8—C13 | −3.2 (7) | C19—C15—C16—C17 | −179.3 (5) |
C13—C8—C9—C10 | 0.8 (7) | C14—N4—C17—C16 | 0.7 (6) |
N1—C8—C9—C10 | −179.4 (4) | C14—N4—C17—C18 | 179.7 (4) |
C8—C9—C10—C11 | −0.3 (7) | C15—C16—C17—N4 | −0.4 (7) |
C9—C10—C11—C12 | −1.1 (7) | C15—C16—C17—C18 | −179.4 (5) |
C9—C10—C11—S1 | 177.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 1.06 | 1.73 | 2.530 (5) | 129 |
O1—H1O···N1 | 0.86 | 1.94 | 2.530 (5) | 124 |
N2—H2N···O1i | 0.86 | 2.20 | 2.871 (4) | 135 |
C9—H9···O2ii | 0.93 | 2.50 | 3.417 (5) | 169 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | 0.61C19H17BrN4O3S·0.39C19H17BrN4O3S |
Mr | 461.34 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 11.7919 (9), 13.9965 (8), 23.5117 (17) |
V (Å3) | 3880.5 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.26 |
Crystal size (mm) | 0.20 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker KAPPA APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.650, 0.725 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19597, 3428, 1961 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.131, 1.00 |
No. of reflections | 3428 |
No. of parameters | 257 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.65 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)..
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 1.06 | 1.73 | 2.530 (5) | 129 |
O1—H1O···N1 | 0.86 | 1.94 | 2.530 (5) | 124 |
N2—H2N···O1i | 0.86 | 2.20 | 2.871 (4) | 135 |
C9—H9···O2ii | 0.93 | 2.50 | 3.417 (5) | 169 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+1/2, −z+1. |
Acknowledgements
The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.
References
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT . Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a result of vital pharmacological effects of sulfonamide and their derivatives, there is a rising attention in synthesizing and biotesting of these derivatives. In the vision of the versatile biological chemistry of sulfonamides, we have synthesized and recently published the crystal structures of several compounds from this group (Chohan et al., 2008a, 2008b; Shad et al., 2008; Tahir et al., 2008). In the same continuation, we herein report the structure of the title compound.
The title compound (I) (Fig. 1) was prepared from sulfamethazine and 5-bromosalicylaldehyde. The crystal of the title compound is isostructural with 4-(5-chloro-2-hydroxybenzylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (II) (Chohan et al., 2008b). In the crystal two tautomers, enolic and zwitterionic, with an approximate ratio of 3:2 coexists, as shown by the refinement of H atom occupancies from the N-H and O-H groups.
We shall restrict discussion to comparison of the bond geometry between (I) and (II). The longest bond in the molecule is C3—Br1, having bond distance 1.890 (5) Å. The bond distances in (I), S1—N2 [1.629 (4) Å] and S1—C11 [1.753 (4) Å] remain equal within experimental errors with those observed in (II). The range of S—O [1.416 (3)–1.431 (3) Å] bond lengths is increased compared to 1.422 (2)–1.4282 (19) Å in (II). The bond angles around the S1-atom are slightly changed. The geometry of intramolecular as well as intermolecular H-bonding is given in Table 1 and shown in Fig 2.