Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010705281X/gd3153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010705281X/gd3153Isup2.hkl |
CCDC reference: 672544
An anhydrous ethanol solution (50 ml) of 4-chloro-2-formyl-6-methoxyphenyl 4-methylbenzenesulfonate (3.41 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of isonicotinohydrazide (1.37 g, 10 mmol) and the mixture was stirred at 350 K for 3 h under N2, giving a white precipitate. The product was isolated, recrystallized from ethanol, and then dried in a vacuum to give pure compound (I) in 72% yield. Colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a solution of ethanol and acetic acid (80:20 v/v).
H atoms were included in calculated positions and refined using a riding-model approximation [constrained C—H and N—H bond lengths and Uiso(H) parameters: 0.93 Å and 1.2Ueq(C) for Csp2 H atoms; 0.96 Å and 1.5Ueq(C) for methyl H atoms; 0.82 Å and 1.5Ueq(O) for the hydroxy H atom; 0.86 Å and 1.2Ueq(N) for the imine H atom]. Please check treatment of Uiso(H) for NH; this has an s.u. value and is not 1.2Ueq.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C21H18ClN3O5S·C2H4O2 | F(000) = 1080 |
Mr = 519.96 | Dx = 1.416 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2260 reflections |
a = 14.886 (3) Å | θ = 2.2–19.8° |
b = 23.190 (4) Å | µ = 0.29 mm−1 |
c = 7.0638 (14) Å | T = 294 K |
V = 2438.5 (8) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.20 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4793 independent reflections |
Radiation source: fine-focus sealed tube | 2849 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→18 |
Tmin = 0.912, Tmax = 0.955 | k = −28→28 |
13425 measured reflections | l = −8→8 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0334P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.20 e Å−3 |
4793 reflections | Δρmin = −0.20 e Å−3 |
322 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0027 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2080 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (7) |
C21H18ClN3O5S·C2H4O2 | V = 2438.5 (8) Å3 |
Mr = 519.96 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.886 (3) Å | µ = 0.29 mm−1 |
b = 23.190 (4) Å | T = 294 K |
c = 7.0638 (14) Å | 0.26 × 0.20 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4793 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2849 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.955 | Rint = 0.069 |
13425 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.092 | Δρmax = 0.20 e Å−3 |
S = 0.97 | Δρmin = −0.20 e Å−3 |
4793 reflections | Absolute structure: Flack (1983), 2080 Friedel pairs |
322 parameters | Absolute structure parameter: −0.01 (7) |
1 restraint |
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 > 2σ(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 | ||
N11 | 1.33949 (17) | 0.46505 (14) | 0.7920 (5) | 0.0550 (9) | |
C12 | 1.3086 (2) | 0.51545 (17) | 0.7335 (6) | 0.0525 (11) | |
H12 | 1.3505 | 0.5428 | 0.6947 | 0.063* | |
C13 | 1.2188 (2) | 0.53074 (14) | 0.7255 (6) | 0.0459 (10) | |
H13 | 1.2012 | 0.5670 | 0.6836 | 0.055* | |
C14 | 1.15569 (18) | 0.49012 (14) | 0.7822 (5) | 0.0365 (8) | |
C15 | 1.1866 (2) | 0.43721 (14) | 0.8455 (5) | 0.0446 (10) | |
H15 | 1.1466 | 0.4089 | 0.8854 | 0.053* | |
C16 | 1.2780 (2) | 0.42734 (16) | 0.8483 (6) | 0.0531 (11) | |
H16 | 1.2978 | 0.3918 | 0.8927 | 0.064* | |
C17 | 1.05883 (19) | 0.50592 (15) | 0.7789 (6) | 0.0394 (8) | |
O17 | 1.03472 (14) | 0.55587 (9) | 0.8076 (4) | 0.0530 (7) | |
N17 | 1.00106 (16) | 0.46234 (12) | 0.7474 (5) | 0.0414 (7) | |
H17 | 1.0205 | 0.4285 | 0.7187 | 0.050* | |
N27 | 0.91027 (15) | 0.47280 (11) | 0.7619 (5) | 0.0411 (7) | |
C27 | 0.8587 (2) | 0.43109 (14) | 0.7159 (5) | 0.0398 (9) | |
H27 | 0.8832 | 0.3964 | 0.6742 | 0.048* | |
C21 | 0.76158 (19) | 0.43778 (13) | 0.7286 (5) | 0.0347 (8) | |
C22 | 0.7222 (2) | 0.49220 (13) | 0.7489 (5) | 0.0386 (8) | |
H22 | 0.7581 | 0.5250 | 0.7548 | 0.046* | |
C23 | 0.6301 (2) | 0.49711 (13) | 0.7604 (6) | 0.0420 (9) | |
Cl1 | 0.58199 (6) | 0.56505 (4) | 0.78214 (17) | 0.0626 (3) | |
C24 | 0.5741 (2) | 0.45001 (13) | 0.7525 (6) | 0.0429 (9) | |
H24 | 0.5121 | 0.4545 | 0.7607 | 0.051* | |
C25 | 0.6115 (2) | 0.39588 (14) | 0.7322 (5) | 0.0373 (9) | |
C26 | 0.70505 (19) | 0.39018 (13) | 0.7225 (5) | 0.0367 (9) | |
O25 | 0.56453 (13) | 0.34591 (9) | 0.7199 (4) | 0.0514 (7) | |
C25A | 0.4709 (2) | 0.34770 (14) | 0.7663 (7) | 0.0623 (11) | |
H25A | 0.4632 | 0.3655 | 0.8880 | 0.093* | |
H25B | 0.4474 | 0.3092 | 0.7697 | 0.093* | |
H25C | 0.4393 | 0.3697 | 0.6723 | 0.093* | |
O26 | 0.74011 (13) | 0.33444 (9) | 0.6966 (3) | 0.0420 (6) | |
S1 | 0.77402 (6) | 0.29942 (4) | 0.87993 (16) | 0.0496 (3) | |
O1 | 0.81179 (15) | 0.24898 (9) | 0.7992 (5) | 0.0708 (9) | |
O2 | 0.82839 (15) | 0.33729 (10) | 0.9892 (4) | 0.0582 (8) | |
C31 | 0.6772 (2) | 0.28251 (14) | 1.0071 (6) | 0.0448 (10) | |
C32 | 0.6561 (3) | 0.31365 (16) | 1.1667 (6) | 0.0609 (11) | |
H32 | 0.6927 | 0.3439 | 1.2059 | 0.073* | |
C33 | 0.5802 (3) | 0.29948 (17) | 1.2677 (7) | 0.0725 (13) | |
H33 | 0.5661 | 0.3206 | 1.3757 | 0.087* | |
C34 | 0.5242 (3) | 0.25491 (18) | 1.2137 (7) | 0.0620 (11) | |
C35 | 0.5469 (3) | 0.22472 (17) | 1.0517 (7) | 0.0606 (12) | |
H35 | 0.5098 | 0.1949 | 1.0115 | 0.073* | |
C36 | 0.6225 (2) | 0.23737 (15) | 0.9482 (6) | 0.0521 (11) | |
H36 | 0.6368 | 0.2161 | 0.8407 | 0.063* | |
C37 | 0.4414 (3) | 0.2396 (2) | 1.3262 (8) | 0.0946 (16) | |
H37A | 0.4222 | 0.2014 | 1.2933 | 0.142* | |
H37B | 0.3943 | 0.2665 | 1.2979 | 0.142* | |
H37C | 0.4550 | 0.2411 | 1.4590 | 0.142* | |
C41 | 0.8649 (3) | 0.64038 (16) | 0.9429 (7) | 0.0504 (11) | |
O41 | 0.87442 (16) | 0.60544 (11) | 0.7997 (4) | 0.0619 (8) | |
H41 | 0.9248 | 0.5912 | 0.8022 | 0.093* | |
O42 | 0.91765 (18) | 0.64319 (11) | 1.0741 (4) | 0.0610 (8) | |
C42 | 0.7810 (3) | 0.67561 (18) | 0.9299 (7) | 0.0738 (14) | |
H42A | 0.7332 | 0.6562 | 0.9952 | 0.111* | |
H42B | 0.7649 | 0.6806 | 0.7994 | 0.111* | |
H42C | 0.7910 | 0.7126 | 0.9870 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0361 (18) | 0.065 (2) | 0.064 (2) | 0.0033 (17) | 0.0011 (17) | 0.001 (2) |
C12 | 0.035 (2) | 0.068 (3) | 0.055 (3) | −0.013 (2) | 0.008 (2) | 0.000 (2) |
C13 | 0.033 (2) | 0.048 (2) | 0.057 (3) | 0.0005 (16) | 0.0049 (19) | −0.001 (2) |
C14 | 0.0269 (17) | 0.047 (2) | 0.036 (2) | 0.0015 (15) | 0.0016 (18) | −0.0045 (19) |
C15 | 0.035 (2) | 0.047 (2) | 0.052 (3) | −0.0006 (16) | −0.0012 (17) | 0.002 (2) |
C16 | 0.041 (2) | 0.056 (2) | 0.062 (3) | 0.0068 (19) | −0.006 (2) | −0.001 (2) |
C17 | 0.0302 (19) | 0.049 (2) | 0.039 (2) | −0.0013 (17) | 0.0006 (19) | 0.000 (2) |
O17 | 0.0395 (13) | 0.0407 (13) | 0.079 (2) | 0.0048 (11) | 0.0003 (13) | −0.0090 (14) |
N17 | 0.0226 (15) | 0.0413 (16) | 0.060 (2) | 0.0017 (13) | 0.0024 (15) | −0.0047 (17) |
N27 | 0.0202 (15) | 0.0489 (17) | 0.054 (2) | 0.0026 (12) | 0.0026 (14) | −0.0033 (17) |
C27 | 0.0297 (19) | 0.045 (2) | 0.044 (3) | 0.0050 (16) | 0.0042 (16) | −0.0028 (19) |
C21 | 0.0243 (17) | 0.0426 (19) | 0.037 (2) | 0.0027 (15) | 0.0000 (15) | −0.0015 (19) |
C22 | 0.0361 (19) | 0.0390 (19) | 0.041 (2) | −0.0034 (15) | −0.0006 (17) | 0.0026 (18) |
C23 | 0.0301 (18) | 0.046 (2) | 0.050 (3) | 0.0090 (15) | 0.0008 (18) | 0.003 (2) |
Cl1 | 0.0496 (6) | 0.0502 (5) | 0.0882 (8) | 0.0136 (4) | 0.0036 (6) | 0.0006 (6) |
C24 | 0.0270 (17) | 0.052 (2) | 0.049 (3) | 0.0034 (16) | 0.0011 (18) | 0.003 (2) |
C25 | 0.0290 (18) | 0.045 (2) | 0.038 (2) | −0.0043 (16) | −0.0016 (16) | 0.0000 (18) |
C26 | 0.0268 (19) | 0.043 (2) | 0.040 (2) | 0.0046 (15) | −0.0010 (16) | −0.0048 (18) |
O25 | 0.0251 (12) | 0.0514 (14) | 0.078 (2) | −0.0034 (11) | 0.0020 (12) | −0.0053 (14) |
C25A | 0.0278 (19) | 0.071 (2) | 0.088 (3) | −0.0106 (17) | 0.007 (2) | 0.003 (3) |
O26 | 0.0299 (12) | 0.0441 (13) | 0.0519 (17) | 0.0056 (10) | −0.0008 (11) | −0.0082 (12) |
S1 | 0.0359 (5) | 0.0413 (5) | 0.0717 (8) | 0.0057 (5) | −0.0040 (5) | −0.0049 (6) |
O1 | 0.0479 (16) | 0.0467 (14) | 0.118 (3) | 0.0205 (12) | 0.0066 (17) | −0.0144 (17) |
O2 | 0.0457 (16) | 0.0529 (15) | 0.076 (2) | −0.0052 (13) | −0.0236 (14) | −0.0009 (14) |
C31 | 0.040 (2) | 0.035 (2) | 0.059 (3) | 0.0060 (17) | −0.0035 (19) | −0.003 (2) |
C32 | 0.061 (3) | 0.053 (2) | 0.069 (3) | −0.005 (2) | −0.002 (2) | −0.012 (2) |
C33 | 0.073 (3) | 0.079 (3) | 0.066 (3) | −0.003 (2) | 0.010 (3) | −0.026 (3) |
C34 | 0.050 (3) | 0.078 (3) | 0.059 (3) | 0.004 (2) | 0.004 (2) | 0.003 (3) |
C35 | 0.051 (3) | 0.055 (3) | 0.076 (4) | −0.002 (2) | −0.001 (2) | −0.004 (2) |
C36 | 0.045 (2) | 0.050 (2) | 0.061 (3) | 0.000 (2) | 0.003 (2) | −0.006 (2) |
C37 | 0.062 (3) | 0.132 (4) | 0.089 (4) | −0.008 (3) | 0.013 (3) | −0.006 (3) |
C41 | 0.047 (3) | 0.041 (2) | 0.064 (3) | 0.0059 (19) | 0.001 (2) | 0.004 (2) |
O41 | 0.0542 (17) | 0.0609 (17) | 0.071 (2) | 0.0195 (13) | −0.0139 (16) | −0.0171 (18) |
O42 | 0.0635 (19) | 0.0542 (16) | 0.065 (2) | 0.0082 (14) | −0.0044 (16) | −0.0024 (15) |
C42 | 0.062 (3) | 0.070 (3) | 0.089 (4) | 0.029 (2) | 0.002 (2) | 0.005 (3) |
S1—O1 | 1.418 (2) | C24—H24 | 0.9300 |
S1—O2 | 1.422 (2) | C16—H16 | 0.9300 |
S1—O26 | 1.610 (2) | C13—C12 | 1.385 (4) |
S1—C31 | 1.743 (4) | C13—H13 | 0.9300 |
Cl1—C23 | 1.738 (3) | C36—C35 | 1.373 (5) |
N17—C17 | 1.346 (4) | C36—C31 | 1.390 (5) |
N17—N27 | 1.377 (3) | C36—H36 | 0.9300 |
N17—H17 | 0.8600 | C12—H12 | 0.9300 |
O17—C17 | 1.229 (3) | C32—C31 | 1.375 (5) |
O26—C26 | 1.406 (3) | C32—C33 | 1.377 (5) |
C26—C21 | 1.389 (4) | C32—H32 | 0.9300 |
C26—C25 | 1.401 (4) | C34—C33 | 1.381 (5) |
C21—C22 | 1.399 (4) | C34—C35 | 1.384 (5) |
C21—C27 | 1.457 (4) | C34—C37 | 1.510 (6) |
C22—C23 | 1.377 (4) | C35—H35 | 0.9300 |
C22—H22 | 0.9300 | C33—H33 | 0.9300 |
O25—C25 | 1.356 (3) | O41—C41 | 1.304 (4) |
O25—C25A | 1.433 (3) | O41—H41 | 0.8200 |
N27—C27 | 1.277 (4) | O42—C41 | 1.216 (4) |
C27—H27 | 0.9300 | C25A—H25A | 0.9600 |
C25—C24 | 1.381 (4) | C25A—H25B | 0.9600 |
C14—C15 | 1.385 (4) | C25A—H25C | 0.9600 |
C14—C13 | 1.389 (4) | C41—C42 | 1.495 (5) |
C14—C17 | 1.488 (4) | C42—H42A | 0.9600 |
N11—C12 | 1.322 (4) | C42—H42B | 0.9600 |
N11—C16 | 1.327 (4) | C42—H42C | 0.9600 |
C15—C16 | 1.380 (4) | C37—H37A | 0.9600 |
C15—H15 | 0.9300 | C37—H37B | 0.9600 |
C24—C23 | 1.376 (4) | C37—H37C | 0.9600 |
O1—S1—O2 | 120.13 (15) | C35—C36—C31 | 118.8 (4) |
O1—S1—O26 | 102.53 (17) | C35—C36—H36 | 120.6 |
O2—S1—O26 | 107.68 (13) | C31—C36—H36 | 120.6 |
O1—S1—C31 | 110.46 (16) | C24—C23—C22 | 122.4 (3) |
O2—S1—C31 | 109.27 (19) | C24—C23—Cl1 | 118.2 (2) |
O26—S1—C31 | 105.61 (14) | C22—C23—Cl1 | 119.4 (3) |
C17—N17—N27 | 118.9 (3) | N11—C12—C13 | 125.1 (3) |
C17—N17—H17 | 120.6 | N11—C12—H12 | 117.5 |
N27—N17—H17 | 120.6 | C13—C12—H12 | 117.5 |
C26—O26—S1 | 118.4 (2) | C31—C32—C33 | 119.2 (4) |
C21—C26—C25 | 121.7 (3) | C31—C32—H32 | 120.4 |
C21—C26—O26 | 120.7 (3) | C33—C32—H32 | 120.4 |
C25—C26—O26 | 117.5 (3) | C33—C34—C35 | 117.4 (4) |
C26—C21—C22 | 117.8 (3) | C33—C34—C37 | 121.6 (5) |
C26—C21—C27 | 121.0 (3) | C35—C34—C37 | 121.0 (4) |
C22—C21—C27 | 121.2 (3) | C32—C31—C36 | 120.5 (4) |
C23—C22—C21 | 119.8 (3) | C32—C31—S1 | 119.5 (3) |
C23—C22—H22 | 120.1 | C36—C31—S1 | 120.0 (3) |
C21—C22—H22 | 120.1 | C36—C35—C34 | 122.1 (4) |
C25—O25—C25A | 117.5 (2) | C36—C35—H35 | 118.9 |
C27—N27—N17 | 115.9 (3) | C34—C35—H35 | 118.9 |
N27—C27—C21 | 120.0 (3) | C32—C33—C34 | 122.0 (4) |
N27—C27—H27 | 120.0 | C32—C33—H33 | 119.0 |
C21—C27—H27 | 120.0 | C34—C33—H33 | 119.0 |
O25—C25—C24 | 125.1 (3) | C41—O41—H41 | 109.5 |
O25—C25—C26 | 115.4 (3) | O25—C25A—H25A | 109.5 |
C24—C25—C26 | 119.5 (3) | O25—C25A—H25B | 109.5 |
C15—C14—C13 | 118.0 (3) | H25A—C25A—H25B | 109.5 |
C15—C14—C17 | 123.0 (3) | O25—C25A—H25C | 109.5 |
C13—C14—C17 | 118.9 (3) | H25A—C25A—H25C | 109.5 |
O17—C17—N17 | 123.3 (3) | H25B—C25A—H25C | 109.5 |
O17—C17—C14 | 120.8 (3) | O42—C41—O41 | 123.6 (4) |
N17—C17—C14 | 115.9 (3) | O42—C41—C42 | 123.9 (4) |
C12—N11—C16 | 115.8 (3) | O41—C41—C42 | 112.5 (4) |
C16—C15—C14 | 118.6 (3) | C41—C42—H42A | 109.5 |
C16—C15—H15 | 120.7 | C41—C42—H42B | 109.5 |
C14—C15—H15 | 120.7 | H42A—C42—H42B | 109.5 |
C23—C24—C25 | 118.7 (3) | C41—C42—H42C | 109.5 |
C23—C24—H24 | 120.6 | H42A—C42—H42C | 109.5 |
C25—C24—H24 | 120.6 | H42B—C42—H42C | 109.5 |
N11—C16—C15 | 124.5 (3) | C34—C37—H37A | 109.5 |
N11—C16—H16 | 117.7 | C34—C37—H37B | 109.5 |
C15—C16—H16 | 117.7 | H37A—C37—H37B | 109.5 |
C12—C13—C14 | 117.9 (3) | C34—C37—H37C | 109.5 |
C12—C13—H13 | 121.1 | H37A—C37—H37C | 109.5 |
C14—C13—H13 | 121.1 | H37B—C37—H37C | 109.5 |
O1—S1—O26—C26 | −174.7 (2) | O25—C25—C24—C23 | −179.1 (3) |
O2—S1—O26—C26 | −47.0 (2) | C26—C25—C24—C23 | 0.8 (5) |
C31—S1—O26—C26 | 69.6 (2) | C12—N11—C16—C15 | 1.3 (6) |
S1—O26—C26—C21 | 85.7 (3) | C14—C15—C16—N11 | −0.8 (6) |
S1—O26—C26—C25 | −97.4 (3) | C15—C14—C13—C12 | 0.9 (5) |
C25—C26—C21—C22 | 1.3 (5) | C17—C14—C13—C12 | 178.7 (3) |
O26—C26—C21—C22 | 178.1 (3) | C25—C24—C23—C22 | −0.1 (6) |
C25—C26—C21—C27 | −179.2 (3) | C25—C24—C23—Cl1 | 179.0 (3) |
O26—C26—C21—C27 | −2.4 (5) | C21—C22—C23—C24 | 0.0 (6) |
C26—C21—C22—C23 | −0.6 (5) | C21—C22—C23—Cl1 | −179.1 (3) |
C27—C21—C22—C23 | 179.9 (3) | C16—N11—C12—C13 | −0.7 (6) |
C17—N17—N27—C27 | 174.6 (3) | C14—C13—C12—N11 | −0.3 (6) |
N17—N27—C27—C21 | 179.3 (3) | C33—C32—C31—C36 | 0.1 (6) |
C26—C21—C27—N27 | −164.9 (3) | C33—C32—C31—S1 | −179.1 (3) |
C22—C21—C27—N27 | 14.5 (5) | C35—C36—C31—C32 | 0.3 (6) |
C25A—O25—C25—C24 | −12.3 (5) | C35—C36—C31—S1 | 179.6 (3) |
C25A—O25—C25—C26 | 167.9 (3) | O1—S1—C31—C32 | 146.7 (3) |
C21—C26—C25—O25 | 178.4 (3) | O2—S1—C31—C32 | 12.4 (3) |
O26—C26—C25—O25 | 1.5 (4) | O26—S1—C31—C32 | −103.1 (3) |
C21—C26—C25—C24 | −1.4 (5) | O1—S1—C31—C36 | −32.6 (4) |
O26—C26—C25—C24 | −178.3 (3) | O2—S1—C31—C36 | −166.8 (3) |
N27—N17—C17—O17 | −5.1 (6) | O26—S1—C31—C36 | 77.6 (3) |
N27—N17—C17—C14 | 173.3 (3) | C31—C36—C35—C34 | −0.9 (6) |
C15—C14—C17—O17 | 146.3 (4) | C33—C34—C35—C36 | 0.9 (6) |
C13—C14—C17—O17 | −31.4 (6) | C37—C34—C35—C36 | −179.2 (4) |
C15—C14—C17—N17 | −32.2 (6) | C31—C32—C33—C34 | −0.1 (6) |
C13—C14—C17—N17 | 150.1 (3) | C35—C34—C33—C32 | −0.4 (6) |
C13—C14—C15—C16 | −0.3 (5) | C37—C34—C33—C32 | 179.7 (4) |
C17—C14—C15—C16 | −178.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O41—H41···O17 | 0.82 | 1.83 | 2.649 (3) | 177 |
N17—H17···O42i | 0.86 | 2.16 | 2.992 (4) | 163 |
C33—H33···O25ii | 0.93 | 2.50 | 3.378 (6) | 157 |
C24—H24···N11iii | 0.93 | 2.59 | 3.521 (4) | 178 |
Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) x, y, z+1; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C21H18ClN3O5S·C2H4O2 |
Mr | 519.96 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 294 |
a, b, c (Å) | 14.886 (3), 23.190 (4), 7.0638 (14) |
V (Å3) | 2438.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.26 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.912, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13425, 4793, 2849 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.092, 0.97 |
No. of reflections | 4793 |
No. of parameters | 322 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Absolute structure | Flack (1983), 2080 Friedel pairs |
Absolute structure parameter | −0.01 (7) |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), PLATON (Spek, 2003), SHELXTL (Sheldrick, 1997b).
N17—N27 | 1.377 (3) | ||
O1—S1—O2 | 120.13 (15) | C17—N17—N27 | 118.9 (3) |
O1—S1—O26 | 102.53 (17) | C26—O26—S1 | 118.4 (2) |
O2—S1—O26 | 107.68 (13) | C27—N27—N17 | 115.9 (3) |
O1—S1—C31 | 110.46 (16) | N27—C27—C21 | 120.0 (3) |
O2—S1—C31 | 109.27 (19) | O17—C17—N17 | 123.3 (3) |
O26—S1—C31 | 105.61 (14) | ||
O1—S1—O26—C26 | −174.7 (2) | C26—C21—C27—N27 | −164.9 (3) |
O2—S1—O26—C26 | −47.0 (2) | C22—C21—C27—N27 | 14.5 (5) |
C31—S1—O26—C26 | 69.6 (2) | N27—N17—C17—O17 | −5.1 (6) |
C17—N17—N27—C27 | 174.6 (3) | N27—N17—C17—C14 | 173.3 (3) |
N17—N27—C27—C21 | 179.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O41—H41···O17 | 0.82 | 1.83 | 2.649 (3) | 177 |
N17—H17···O42i | 0.86 | 2.16 | 2.992 (4) | 163 |
C33—H33···O25ii | 0.93 | 2.50 | 3.378 (6) | 157 |
C24—H24···N11iii | 0.93 | 2.59 | 3.521 (4) | 178 |
Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) x, y, z+1; (iii) x−1, y, z. |
There has been steady growth of interest in the structure and reactivity of Schiff bases owing to their potential biological activities, such as antibacterial and antitumor (Kahwa et al., 1986; Santos et al., 2001). Isonicotinohydrazide forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them have been reported (Wardell, de Souza, Ferreira et al., 2005; Wardell, de Souza, Wardell et al., 2005; Wardell et al., 2006; Low et al., 2006). In order to obtain more detailed information on the structural conformation of the molecule, which may be of value in structure–activity analysis, we report here the synthesis and structure of the title compound, (I).
Within the hydrazine component in (I), both N atoms (N17 and N27) have effectively planar coordination, and the N—N bond distance (Table 1) is typical of the value in hydrazines with both N atoms having planar coordination (the mean value is 1.401 Å; Allen et al., 1987). In addition, the central spacer unit between atoms C17 and C21 (Fig. 1) adopts a nearly planar all-trans conformation, as shown by the key torsion angles (Table 1).
In (I), (Fig. 1), the acetic acid molecule is effectively tethered to the hydrazone component by a combination of two independent hydrogen bonds, one of O—H···O and one of N—H···O type (Fig. 2 and Table 2). Acetic acid atom O41 acts as a hydrogen-bond donor to hydrazone atom O17. At the same time, hydrazone atom N17 in the molecule at (x, y, z) acts as a hydrogen-bond donor to acetic acid atom O42 in the molecule at (2 - x, 1 - y, -1/2 + z). In addition, atom C33 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O25 in the molecule at (x, y, 1 + z), so generating by translation a C22(8)C(9)R55(33) chain of fused rings (Bernstein et al., 1995) running parallel to the [001] direction.
Atom C24 in the molecule at (1 + x, y, z) acts as a hydrogen-bond donor to pyridyl atom N11 in the molecule at (x, y, z), so forming a C(13) chain running parallel to the [100] direction. In addition, atom C33 in the molecule at (x, y, -1 + z) in turn acts as a hydrogen-bond donor to atom O25 in the molecule at (x, y, z), so forming a C(9) chain running parallel to the [001] direction. The combination of the [100] and [001] chains then generate a sheet parallel to (010) containing R44(42) rings (Fig. 3). In combination with the C22(8)C(9)R55(33) chain of rings (Fig. 2), these hydrogen bonds then generate a complex network containing alternating R44(42), R55(33) and R66(40) rings (Fig. 4).