Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808005606/fj2100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536808005606/fj2100Isup2.hkl |
CCDC reference: 684462
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.148
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT352_ALERT_3_C Short N-H Bond (0.87A) N2 - H2 ... 0.71 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C18
Alert level G RADNT01_ALERT_1_G Extra text has been found in the _diffrn_radiation_type field. Radiation given as MoK\a radiation Radiation identified as Mo K\a
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Sulfamethazine (0.5566 g, 2 mmol) in ethanol (15 ml) was reacted with ethanolic (10 ml) solution of 5-chlorosalicylaldehyde (0.3131 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 10 days crystals of the title compound were obtained.
The coordinates of the hydroxy and amide H-atoms were freely refined. Other H-atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl carbons respectively. The Uiso(H) = xUeq(C, N, O), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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 (Farrugia, 1999) and PLATON (Spek, 2003).
C19H17ClN4O3S | Dx = 1.440 Mg m−3 |
Mr = 416.88 | Melting point: 497 K |
Orthorhombic, Pbca | Mo Kα radiation radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2797 reflections |
a = 11.7332 (7) Å | θ = 1.7–28.3° |
b = 13.8506 (6) Å | µ = 0.34 mm−1 |
c = 23.6635 (14) Å | T = 296 K |
V = 3845.6 (4) Å3 | Prismatic, red |
Z = 8 | 0.22 × 0.18 × 0.14 mm |
F(000) = 1728 |
Bruker Kappa APEXII CCD diffractometer | 4787 independent reflections |
Radiation source: fine-focus sealed tube | 2797 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 7.40 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −17→18 |
Tmin = 0.940, Tmax = 0.958 | l = −31→30 |
21114 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0488P)2 + 2.8076P] where P = (Fo2 + 2Fc2)/3 |
2797 reflections | (Δ/σ)max < 0.001 |
259 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C19H17ClN4O3S | V = 3845.6 (4) Å3 |
Mr = 416.88 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.7332 (7) Å | µ = 0.34 mm−1 |
b = 13.8506 (6) Å | T = 296 K |
c = 23.6635 (14) Å | 0.22 × 0.18 × 0.14 mm |
Bruker Kappa APEXII CCD diffractometer | 4787 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2797 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.958 | Rint = 0.043 |
21114 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.32 e Å−3 |
2797 reflections | Δρmin = −0.28 e Å−3 |
259 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 | ||
Cl1 | 1.17644 (10) | −0.26287 (7) | −0.12764 (5) | 0.0872 (3) | |
S1 | 0.40720 (6) | 0.12989 (5) | 0.10363 (3) | 0.04261 (19) | |
O1 | 0.9575 (2) | 0.11270 (16) | −0.10024 (12) | 0.0767 (8) | |
H1 | 0.902 (4) | 0.105 (3) | −0.0865 (19) | 0.092* | |
O2 | 0.34086 (18) | 0.19106 (14) | 0.06787 (9) | 0.0566 (6) | |
O3 | 0.35672 (17) | 0.04443 (14) | 0.12555 (9) | 0.0533 (5) | |
N1 | 0.82013 (19) | 0.03779 (16) | −0.03019 (10) | 0.0449 (6) | |
N2 | 0.4449 (2) | 0.20143 (17) | 0.15497 (11) | 0.0484 (6) | |
H2 | 0.442 (3) | 0.252 (2) | 0.1502 (14) | 0.058* | |
N3 | 0.5377 (2) | 0.25140 (17) | 0.23450 (10) | 0.0504 (6) | |
N4 | 0.5464 (2) | 0.08644 (17) | 0.20508 (10) | 0.0494 (6) | |
C1 | 0.9660 (2) | −0.05366 (19) | −0.07463 (12) | 0.0438 (6) | |
C2 | 1.0209 (3) | −0.1429 (2) | −0.08168 (13) | 0.0535 (8) | |
H2A | 0.9970 | −0.1960 | −0.0608 | 0.064* | |
C3 | 1.1091 (3) | −0.1523 (2) | −0.11879 (14) | 0.0546 (8) | |
C4 | 1.1463 (3) | −0.0739 (2) | −0.14968 (16) | 0.0685 (10) | |
H4A | 1.2067 | −0.0811 | −0.1748 | 0.082* | |
C5 | 1.0950 (3) | 0.0147 (2) | −0.14375 (16) | 0.0703 (10) | |
H5 | 1.1202 | 0.0668 | −0.1651 | 0.084* | |
C6 | 1.0057 (3) | 0.0265 (2) | −0.10596 (14) | 0.0543 (8) | |
C7 | 0.8701 (2) | −0.0437 (2) | −0.03688 (12) | 0.0479 (7) | |
H7 | 0.8442 | −0.0973 | −0.0171 | 0.058* | |
C8 | 0.7233 (2) | 0.05312 (19) | 0.00426 (11) | 0.0412 (6) | |
C9 | 0.6811 (3) | 0.1460 (2) | 0.00458 (14) | 0.0565 (8) | |
H9 | 0.7170 | 0.1935 | −0.0168 | 0.068* | |
C10 | 0.5868 (3) | 0.1695 (2) | 0.03601 (14) | 0.0561 (8) | |
H10 | 0.5597 | 0.2325 | 0.0364 | 0.067* | |
C11 | 0.5325 (2) | 0.09899 (18) | 0.06706 (11) | 0.0390 (6) | |
C12 | 0.5748 (2) | 0.00607 (19) | 0.06810 (12) | 0.0448 (7) | |
H12 | 0.5395 | −0.0409 | 0.0901 | 0.054* | |
C13 | 0.6696 (2) | −0.01695 (19) | 0.03636 (12) | 0.0479 (7) | |
H13 | 0.6976 | −0.0798 | 0.0365 | 0.057* | |
C14 | 0.5142 (2) | 0.1773 (2) | 0.20062 (11) | 0.0432 (6) | |
C15 | 0.6017 (3) | 0.2304 (2) | 0.27940 (13) | 0.0577 (8) | |
C16 | 0.6394 (3) | 0.1374 (3) | 0.28828 (14) | 0.0631 (9) | |
H16 | 0.6841 | 0.1229 | 0.3196 | 0.076* | |
C17 | 0.6107 (3) | 0.0666 (2) | 0.25061 (14) | 0.0552 (8) | |
C18 | 0.6497 (3) | −0.0362 (3) | 0.25674 (17) | 0.0825 (12) | |
H18A | 0.6198 | −0.0741 | 0.2262 | 0.124* | |
H18B | 0.6227 | −0.0618 | 0.2920 | 0.124* | |
H18C | 0.7314 | −0.0385 | 0.2560 | 0.124* | |
C19 | 0.6268 (4) | 0.3114 (3) | 0.31925 (16) | 0.0894 (13) | |
H19A | 0.5930 | 0.3698 | 0.3053 | 0.134* | |
H19B | 0.7078 | 0.3198 | 0.3223 | 0.134* | |
H19C | 0.5958 | 0.2966 | 0.3558 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0896 (8) | 0.0611 (5) | 0.1110 (9) | 0.0210 (5) | 0.0139 (6) | −0.0059 (5) |
S1 | 0.0421 (4) | 0.0436 (4) | 0.0421 (4) | 0.0046 (3) | −0.0031 (3) | 0.0001 (3) |
O1 | 0.0854 (19) | 0.0453 (12) | 0.099 (2) | 0.0069 (12) | 0.0452 (16) | 0.0174 (12) |
O2 | 0.0549 (13) | 0.0587 (12) | 0.0562 (13) | 0.0154 (10) | −0.0166 (10) | 0.0013 (10) |
O3 | 0.0474 (12) | 0.0526 (11) | 0.0601 (13) | −0.0030 (9) | 0.0087 (10) | 0.0007 (10) |
N1 | 0.0447 (13) | 0.0476 (13) | 0.0424 (14) | −0.0036 (11) | 0.0031 (11) | −0.0003 (10) |
N2 | 0.0594 (16) | 0.0417 (12) | 0.0442 (14) | 0.0095 (12) | −0.0076 (12) | −0.0026 (11) |
N3 | 0.0539 (15) | 0.0534 (14) | 0.0440 (14) | −0.0051 (12) | −0.0003 (12) | −0.0005 (11) |
N4 | 0.0525 (15) | 0.0515 (14) | 0.0442 (14) | 0.0134 (11) | −0.0001 (11) | 0.0037 (11) |
C1 | 0.0435 (16) | 0.0447 (14) | 0.0433 (16) | −0.0046 (12) | −0.0021 (13) | −0.0001 (12) |
C2 | 0.060 (2) | 0.0440 (15) | 0.0562 (19) | −0.0030 (14) | 0.0014 (15) | 0.0036 (14) |
C3 | 0.0499 (18) | 0.0502 (16) | 0.064 (2) | 0.0036 (14) | 0.0001 (15) | −0.0047 (14) |
C4 | 0.056 (2) | 0.068 (2) | 0.081 (3) | 0.0001 (17) | 0.0257 (18) | −0.0003 (19) |
C5 | 0.068 (2) | 0.0556 (19) | 0.087 (3) | −0.0026 (17) | 0.030 (2) | 0.0141 (18) |
C6 | 0.0564 (19) | 0.0460 (16) | 0.060 (2) | −0.0028 (14) | 0.0102 (16) | 0.0026 (14) |
C7 | 0.0500 (17) | 0.0491 (15) | 0.0447 (16) | −0.0117 (13) | −0.0008 (14) | 0.0043 (13) |
C8 | 0.0442 (15) | 0.0434 (14) | 0.0360 (14) | −0.0049 (12) | 0.0003 (12) | −0.0006 (12) |
C9 | 0.063 (2) | 0.0436 (16) | 0.063 (2) | −0.0043 (14) | 0.0172 (16) | 0.0136 (14) |
C10 | 0.065 (2) | 0.0387 (14) | 0.064 (2) | 0.0033 (14) | 0.0120 (17) | 0.0105 (14) |
C11 | 0.0428 (15) | 0.0409 (13) | 0.0334 (14) | −0.0002 (11) | −0.0030 (11) | 0.0017 (11) |
C12 | 0.0522 (17) | 0.0375 (14) | 0.0446 (16) | −0.0021 (12) | 0.0090 (13) | 0.0071 (12) |
C13 | 0.0533 (18) | 0.0386 (14) | 0.0517 (18) | 0.0031 (12) | 0.0073 (14) | 0.0044 (13) |
C14 | 0.0405 (15) | 0.0512 (16) | 0.0378 (15) | 0.0043 (13) | 0.0040 (12) | 0.0023 (12) |
C15 | 0.0516 (19) | 0.076 (2) | 0.0454 (18) | −0.0206 (16) | −0.0016 (15) | 0.0042 (16) |
C16 | 0.0472 (18) | 0.093 (2) | 0.0489 (19) | −0.0113 (17) | −0.0124 (15) | 0.0199 (18) |
C17 | 0.0459 (17) | 0.0693 (19) | 0.0504 (18) | 0.0065 (15) | 0.0032 (14) | 0.0173 (16) |
C18 | 0.081 (3) | 0.081 (2) | 0.086 (3) | 0.026 (2) | −0.007 (2) | 0.027 (2) |
C19 | 0.105 (3) | 0.096 (3) | 0.068 (2) | −0.046 (3) | −0.019 (2) | −0.004 (2) |
Cl1—C3 | 1.736 (3) | C5—H5 | 0.9300 |
S1—O3 | 1.422 (2) | C7—H7 | 0.9300 |
S1—O2 | 1.4282 (19) | C8—C9 | 1.379 (4) |
S1—N2 | 1.629 (3) | C8—C13 | 1.384 (4) |
S1—C11 | 1.759 (3) | C9—C10 | 1.371 (4) |
O1—C6 | 1.328 (4) | C9—H9 | 0.9300 |
O1—H1 | 0.74 (4) | C10—C11 | 1.378 (4) |
N1—C7 | 1.282 (4) | C10—H10 | 0.9300 |
N1—C8 | 1.414 (3) | C11—C12 | 1.379 (3) |
N2—C14 | 1.393 (4) | C12—C13 | 1.380 (4) |
N2—H2 | 0.71 (3) | C12—H12 | 0.9300 |
N3—C14 | 1.332 (3) | C13—H13 | 0.9300 |
N3—C15 | 1.333 (4) | C15—C16 | 1.378 (5) |
N4—C14 | 1.318 (3) | C15—C19 | 1.495 (5) |
N4—C17 | 1.343 (4) | C16—C17 | 1.368 (5) |
C1—C2 | 1.404 (4) | C16—H16 | 0.9300 |
C1—C6 | 1.414 (4) | C17—C18 | 1.503 (4) |
C1—C7 | 1.443 (4) | C18—H18A | 0.9600 |
C2—C3 | 1.363 (4) | C18—H18B | 0.9600 |
C2—H2A | 0.9300 | C18—H18C | 0.9600 |
C3—C4 | 1.380 (4) | C19—H19A | 0.9600 |
C4—C5 | 1.373 (4) | C19—H19B | 0.9600 |
C4—H4A | 0.9300 | C19—H19C | 0.9600 |
C5—C6 | 1.388 (4) | ||
O3—S1—O2 | 118.89 (13) | C10—C9—H9 | 119.6 |
O3—S1—N2 | 110.33 (13) | C8—C9—H9 | 119.6 |
O2—S1—N2 | 103.22 (12) | C9—C10—C11 | 119.6 (3) |
O3—S1—C11 | 108.98 (12) | C9—C10—H10 | 120.2 |
O2—S1—C11 | 107.97 (13) | C11—C10—H10 | 120.2 |
N2—S1—C11 | 106.75 (13) | C10—C11—C12 | 120.3 (3) |
C6—O1—H1 | 107 (3) | C10—C11—S1 | 118.5 (2) |
C7—N1—C8 | 124.8 (2) | C12—C11—S1 | 121.3 (2) |
C14—N2—S1 | 126.2 (2) | C11—C12—C13 | 119.7 (2) |
C14—N2—H2 | 113 (3) | C11—C12—H12 | 120.1 |
S1—N2—H2 | 118 (3) | C13—C12—H12 | 120.1 |
C14—N3—C15 | 115.3 (3) | C12—C13—C8 | 120.2 (3) |
C14—N4—C17 | 114.9 (3) | C12—C13—H13 | 119.9 |
C2—C1—C6 | 118.5 (3) | C8—C13—H13 | 119.9 |
C2—C1—C7 | 121.1 (3) | N4—C14—N3 | 128.9 (3) |
C6—C1—C7 | 120.4 (3) | N4—C14—N2 | 117.3 (3) |
C3—C2—C1 | 120.6 (3) | N3—C14—N2 | 113.8 (2) |
C3—C2—H2A | 119.7 | N3—C15—C16 | 120.5 (3) |
C1—C2—H2A | 119.7 | N3—C15—C19 | 116.7 (3) |
C2—C3—C4 | 120.4 (3) | C16—C15—C19 | 122.8 (3) |
C2—C3—Cl1 | 120.5 (2) | C17—C16—C15 | 119.4 (3) |
C4—C3—Cl1 | 119.1 (3) | C17—C16—H16 | 120.3 |
C5—C4—C3 | 120.7 (3) | C15—C16—H16 | 120.3 |
C5—C4—H4A | 119.7 | N4—C17—C16 | 120.9 (3) |
C3—C4—H4A | 119.7 | N4—C17—C18 | 116.3 (3) |
C4—C5—C6 | 120.1 (3) | C16—C17—C18 | 122.8 (3) |
C4—C5—H5 | 119.9 | C17—C18—H18A | 109.5 |
C6—C5—H5 | 119.9 | C17—C18—H18B | 109.5 |
O1—C6—C5 | 119.5 (3) | H18A—C18—H18B | 109.5 |
O1—C6—C1 | 120.8 (3) | C17—C18—H18C | 109.5 |
C5—C6—C1 | 119.6 (3) | H18A—C18—H18C | 109.5 |
N1—C7—C1 | 121.2 (3) | H18B—C18—H18C | 109.5 |
N1—C7—H7 | 119.4 | C15—C19—H19A | 109.5 |
C1—C7—H7 | 119.4 | C15—C19—H19B | 109.5 |
C9—C8—C13 | 119.2 (3) | H19A—C19—H19B | 109.5 |
C9—C8—N1 | 115.6 (2) | C15—C19—H19C | 109.5 |
C13—C8—N1 | 125.2 (2) | H19A—C19—H19C | 109.5 |
C10—C9—C8 | 120.9 (3) | H19B—C19—H19C | 109.5 |
O3—S1—N2—C14 | 54.0 (3) | O3—S1—C11—C10 | 171.4 (2) |
O2—S1—N2—C14 | −178.0 (3) | O2—S1—C11—C10 | 41.0 (3) |
C11—S1—N2—C14 | −64.3 (3) | N2—S1—C11—C10 | −69.4 (3) |
C6—C1—C2—C3 | −1.3 (4) | O3—S1—C11—C12 | −7.1 (3) |
C7—C1—C2—C3 | 177.9 (3) | O2—S1—C11—C12 | −137.5 (2) |
C1—C2—C3—C4 | 0.6 (5) | N2—S1—C11—C12 | 112.0 (2) |
C1—C2—C3—Cl1 | −179.7 (2) | C10—C11—C12—C13 | −2.2 (4) |
C2—C3—C4—C5 | −0.3 (6) | S1—C11—C12—C13 | 176.3 (2) |
Cl1—C3—C4—C5 | −180.0 (3) | C11—C12—C13—C8 | 1.0 (4) |
C3—C4—C5—C6 | 0.7 (6) | C9—C8—C13—C12 | 0.2 (4) |
C4—C5—C6—O1 | 179.4 (4) | N1—C8—C13—C12 | −179.4 (3) |
C4—C5—C6—C1 | −1.5 (6) | C17—N4—C14—N3 | 0.9 (4) |
C2—C1—C6—O1 | −179.1 (3) | C17—N4—C14—N2 | −178.4 (3) |
C7—C1—C6—O1 | 1.7 (5) | C15—N3—C14—N4 | −0.9 (4) |
C2—C1—C6—C5 | 1.8 (5) | C15—N3—C14—N2 | 178.4 (3) |
C7—C1—C6—C5 | −177.4 (3) | S1—N2—C14—N4 | −4.9 (4) |
C8—N1—C7—C1 | 177.5 (2) | S1—N2—C14—N3 | 175.7 (2) |
C2—C1—C7—N1 | 179.7 (3) | C14—N3—C15—C16 | 0.4 (4) |
C6—C1—C7—N1 | −1.1 (4) | C14—N3—C15—C19 | −178.2 (3) |
C7—N1—C8—C9 | −178.6 (3) | N3—C15—C16—C17 | −0.1 (5) |
C7—N1—C8—C13 | 1.1 (4) | C19—C15—C16—C17 | 178.4 (3) |
C13—C8—C9—C10 | −0.2 (5) | C14—N4—C17—C16 | −0.5 (4) |
N1—C8—C9—C10 | 179.4 (3) | C14—N4—C17—C18 | −179.5 (3) |
C8—C9—C10—C11 | −0.9 (5) | C15—C16—C17—N4 | 0.2 (5) |
C9—C10—C11—C12 | 2.2 (5) | C15—C16—C17—C18 | 179.1 (3) |
C9—C10—C11—S1 | −176.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.73 (5) | 1.90 (4) | 2.534 (3) | 146 (5) |
N2—H2···O1i | 0.71 (3) | 2.22 (3) | 2.886 (3) | 156 (3) |
C9—H9···O2ii | 0.93 | 2.48 | 3.398 (4) | 171 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H17ClN4O3S |
Mr | 416.88 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 11.7332 (7), 13.8506 (6), 23.6635 (14) |
V (Å3) | 3845.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.22 × 0.18 × 0.14 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.940, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21114, 4787, 2797 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.148, 1.05 |
No. of reflections | 2797 |
No. of parameters | 259 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.28 |
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 (Farrugia, 1999) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.73 (5) | 1.90 (4) | 2.534 (3) | 146 (5) |
N2—H2···O1i | 0.71 (3) | 2.22 (3) | 2.886 (3) | 156 (3) |
C9—H9···O2ii | 0.93 | 2.48 | 3.398 (4) | 171 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, −z. |
Sulfonamides have widely been recognized for their wide variety of pharmacological activities such as antibacterial, antitumor, anti-carbonic anhydrase, diuretic, hypoglycaemic, antithyroid and protease inhibitory activity. Sulfonamides have also been used clinically as antimalarial agents (Zareef et al., 2007), particularly sulfadiazine and sulfadoxine. Due to their significant pharmacology applications and widespread use in medicine, these compounds have also gained attention in bio-inorganic and metal-based (Chohan et al., 2007) drug chemistry. In continuation to the preparation of schiff base ligands with various sulfa drugs and halogen substituated aldehydes (Shad et al., 2008), we report herein the structure of the title compound.
The title compound (I), is a Schiff base ligand containing sulfamethazine and 5-chlorosalicylaldehyde. The crystal structure (Basak et al., 1983) of (II) sulfamethazine:[4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide] have been reported. The search in Cambridge Crystallographic Data Center showed that no crystal structure of 5-chlorosalicylaldehyde as an individual moiety is reported. Few structures containing the later have been reported such as 5-chlorosalicylaldehyde salicylhydrazone (Yang, 2006). The mutual effect of sulfamethazine and the 5-chlorosalicylaldehyde in solid form is observed by enlarging the bond lengths N1—C8 [1.414 (3) Å], S1—C11 [1.759 (3) Å] compared to 1.367 (3)° and 1.746 (3) Å respectively as reported in (II). The bond distances in the 4,6-dimethyl-2-pyrimidinyl moiety of sulfamethazine remained same whithin experimental errors. The observed bond angles C11—S1—N2 and S1—N2—C14 have values of 106.75 (13)°, 126.2 (2)° in comparison to 108.2 (1)° and 128.0 (2)° respectively. The torsion angle C11—S1—N2—C14: -64.3 (3)° in the title compound compared to 83.0 (3)° shows that the 4,6-dimethyl-2-pyrimidinyl moiety becomes almost in trans position. The observed change in 5-chlorosalicylaldehyde moiety, is mainly of bond distances C6—O1 [1.328 (4) Å] and Cl1—C5 [1.736 (3) Å], whereas these values are 1.347 (5) Å and 1.746 (4) Å as reported in 5-chlorosalicylaldehyde salicylhydrazone. The coordinates of H-atoms attached to O1 and N2 were refined. The rings A(C14/N3/C15/C16/C17/N4), B(C1/C2/C3/C4/C5/C6) and C(C8/C9/C10/C11/C12/C13), make dihedral angles A/B[78.95 (8)°], A/C[83.50 (8)°] and B/C[4.57 (19)°] respectively. The sulfonyl group (O2/S1/O3) have a dihedral angle of 56.36 (11)° with ring (B) and with ring (A), it is 54.25 (14)°. An intramolecular H-bond of O—H···N type complete six-membered ring, as shown in Fig 1. The two intermolecular H-bonds of C—H···O and N—H···O form a ten membered ring by sharing a six membered ring due to intramolecular H-bond as in Fig 2. The detail of H-bonds is given in Table 1.