Acta Cryst. (2008). E64, o1769 [ doi:10.1107/S1600536808025932 ]
The two independent molecules in the asymmetric unit of the title compound, C15H16N2O3S, are each linked by an N-H
Osulfonyl hydrogen bond into a linear chain that runs along the shortest axis of the triclinic unit cell. The hydroxy groups are engaged in intramolecular hydrogen bonding and the amino N atom shows pyramidal coordination.
The Schiff base was prepared by refluxing by benzene sulfanohydrazide (0.40 g, 0.64 mmol) and 5-methyl-2-hydroxyacetophenone (0.10 g, 0.64 mmol) in ethanol for 2 h. The product was filtered and recrystallized from ethanol.
Carbon-bound hydrogen atoms were generated geometrically (C—H 0.95 to 98 Å), and were treated as riding, with U(H) 1.2 to 1.5 times Ueq(C). The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints (N–H 0.88±0.01, O–H 0.84±0.01 Å); their temperature factors were freely refined.
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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
![[Figure 1]](./bq2092fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot of the asymmetric unit of (I) (Barbour, 2001) at the 70% probability level. Dashed line indicates H-bonding. |
| C15H16N2O3S | Z = 4 |
| Mr = 304.36 | F000 = 640 |
| Triclinic, P1 | Dx = 1.415 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 5.1547 (1) Å | Cell parameters from 7775 reflections |
| b = 17.0321 (2) Å | θ = 2.2–30.4º |
| c = 18.2635 (1) Å | µ = 0.24 mm−1 |
| α = 63.192 (1)º | T = 100 (2) K |
| β = 88.577 (1)º | Block, colorless |
| γ = 86.345 (1)º | 0.18 × 0.14 × 0.06 mm |
| V = 1428.19 (4) Å3 |
| Bruker SMART APEX diffractometer | 6415 independent reflections |
| Radiation source: fine-focus sealed tube | 5603 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.018 |
| T = 100(2) K | θmax = 27.5º |
| ω scans | θmin = 1.3º |
| Absorption correction: Multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
| Tmin = 0.958, Tmax = 0.986 | k = −22→22 |
| 12657 measured reflections | l = −23→22 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0741P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max = 0.001 |
| 6415 reflections | Δρmax = 0.54 e Å−3 |
| 399 parameters | Δρmin = −0.58 e Å−3 |
| 4 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C15H16N2O3S | γ = 86.345 (1)º |
| Mr = 304.36 | V = 1428.19 (4) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 5.1547 (1) Å | Mo Kα |
| b = 17.0321 (2) Å | µ = 0.24 mm−1 |
| c = 18.2635 (1) Å | T = 100 (2) K |
| α = 63.192 (1)º | 0.18 × 0.14 × 0.06 mm |
| β = 88.577 (1)º |
| Bruker SMART APEX diffractometer | 6415 independent reflections |
| Absorption correction: Multi-scan (SADABS; Sheldrick, 1996) | 5603 reflections with I > 2σ(I) |
| Tmin = 0.958, Tmax = 0.986 | Rint = 0.018 |
| 12657 measured reflections |
| R[F2 > 2σ(F2)] = 0.042 | 4 restraints |
| wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | Δρmax = 0.54 e Å−3 |
| 6415 reflections | Δρmin = −0.58 e Å−3 |
| 399 parameters |
| x | y | z | Uiso*/Ueq | ||
| S1 | 1.00270 (8) | 0.59346 (3) | 0.36837 (3) | 0.01389 (12) | |
| S2 | 0.23309 (8) | 0.87206 (3) | 0.94073 (3) | 0.01512 (12) | |
| O1 | 1.1834 (3) | 0.79133 (9) | 0.43334 (9) | 0.0198 (3) | |
| O2 | 1.2673 (3) | 0.59821 (9) | 0.38815 (8) | 0.0181 (3) | |
| O3 | 0.9214 (3) | 0.51803 (9) | 0.36199 (9) | 0.0190 (3) | |
| O4 | 0.1038 (3) | 0.73122 (10) | 0.80833 (9) | 0.0238 (3) | |
| O5 | −0.0223 (3) | 0.84056 (10) | 0.94695 (9) | 0.0206 (3) | |
| O6 | 0.3106 (3) | 0.90879 (9) | 0.99282 (9) | 0.0196 (3) | |
| N1 | 0.8800 (3) | 0.66835 (10) | 0.45822 (10) | 0.0153 (3) | |
| N2 | 0.8209 (3) | 0.59890 (11) | 0.44147 (10) | 0.0150 (3) | |
| N3 | 0.3956 (3) | 0.74366 (11) | 0.91380 (10) | 0.0163 (3) | |
| N4 | 0.4405 (3) | 0.78638 (11) | 0.96235 (10) | 0.0159 (3) | |
| C1 | 1.0427 (4) | 0.80153 (13) | 0.49302 (12) | 0.0165 (4) | |
| C2 | 1.1112 (4) | 0.86743 (13) | 0.51253 (13) | 0.0200 (4) | |
| H2 | 1.2525 | 0.9023 | 0.4851 | 0.024* | |
| C3 | 0.9752 (4) | 0.88270 (13) | 0.57162 (13) | 0.0205 (4) | |
| H3 | 1.0244 | 0.9282 | 0.5840 | 0.025* | |
| C4 | 0.7677 (4) | 0.83279 (13) | 0.61327 (12) | 0.0189 (4) | |
| C5 | 0.7016 (4) | 0.76637 (13) | 0.59405 (12) | 0.0173 (4) | |
| H5 | 0.5617 | 0.7313 | 0.6225 | 0.021* | |
| C6 | 0.8335 (4) | 0.74898 (12) | 0.53418 (11) | 0.0151 (4) | |
| C7 | 0.6197 (4) | 0.84927 (15) | 0.67793 (14) | 0.0243 (4) | |
| H7A | 0.4382 | 0.8351 | 0.6783 | 0.037* | |
| H7B | 0.6264 | 0.9114 | 0.6656 | 0.037* | |
| H7C | 0.6985 | 0.8120 | 0.7318 | 0.037* | |
| C8 | 0.7526 (4) | 0.67782 (12) | 0.51600 (11) | 0.0152 (4) | |
| C9 | 0.5429 (4) | 0.61962 (13) | 0.56463 (13) | 0.0208 (4) | |
| H9A | 0.4909 | 0.5847 | 0.5376 | 0.031* | |
| H9B | 0.3926 | 0.6559 | 0.5682 | 0.031* | |
| H9C | 0.6077 | 0.5800 | 0.6199 | 0.031* | |
| C10 | 0.9242 (4) | 0.68803 (12) | 0.27615 (11) | 0.0153 (4) | |
| C11 | 0.7132 (4) | 0.68724 (14) | 0.23050 (12) | 0.0200 (4) | |
| H11 | 0.6139 | 0.6367 | 0.2489 | 0.024* | |
| C12 | 0.6499 (4) | 0.76133 (14) | 0.15765 (12) | 0.0219 (4) | |
| H12 | 0.5065 | 0.7616 | 0.1258 | 0.026* | |
| C13 | 0.7956 (4) | 0.83520 (14) | 0.13098 (12) | 0.0224 (4) | |
| H13 | 0.7512 | 0.8859 | 0.0811 | 0.027* | |
| C14 | 1.0053 (4) | 0.83500 (14) | 0.17703 (13) | 0.0242 (4) | |
| H14 | 1.1050 | 0.8855 | 0.1584 | 0.029* | |
| C15 | 1.0708 (4) | 0.76134 (14) | 0.25038 (12) | 0.0206 (4) | |
| H15 | 1.2136 | 0.7612 | 0.2823 | 0.025* | |
| C16 | 0.2653 (4) | 0.66099 (14) | 0.81883 (12) | 0.0194 (4) | |
| C17 | 0.2155 (4) | 0.61764 (15) | 0.77206 (13) | 0.0230 (4) | |
| H17 | 0.0730 | 0.6380 | 0.7348 | 0.028* | |
| C18 | 0.3706 (4) | 0.54571 (14) | 0.77928 (13) | 0.0222 (4) | |
| H18 | 0.3328 | 0.5170 | 0.7470 | 0.027* | |
| C19 | 0.5829 (4) | 0.51392 (14) | 0.83316 (13) | 0.0209 (4) | |
| C20 | 0.6317 (4) | 0.55738 (13) | 0.87953 (12) | 0.0189 (4) | |
| H20 | 0.7759 | 0.5367 | 0.9161 | 0.023* | |
| C21 | 0.4775 (4) | 0.63059 (13) | 0.87480 (12) | 0.0171 (4) | |
| C22 | 0.7530 (4) | 0.43515 (15) | 0.84084 (15) | 0.0273 (5) | |
| H22A | 0.9231 | 0.4364 | 0.8630 | 0.041* | |
| H22B | 0.7753 | 0.4369 | 0.7867 | 0.041* | |
| H22C | 0.6709 | 0.3810 | 0.8779 | 0.041* | |
| C23 | 0.5394 (4) | 0.67411 (13) | 0.92575 (11) | 0.0162 (4) | |
| C24 | 0.7550 (4) | 0.63615 (13) | 0.98790 (12) | 0.0196 (4) | |
| H24A | 0.7488 | 0.6660 | 1.0229 | 0.029* | |
| H24B | 0.9226 | 0.6446 | 0.9596 | 0.029* | |
| H24C | 0.7344 | 0.5731 | 1.0217 | 0.029* | |
| C25 | 0.2788 (4) | 0.94842 (12) | 0.83776 (11) | 0.0157 (4) | |
| C26 | 0.4827 (4) | 1.00410 (13) | 0.81963 (13) | 0.0202 (4) | |
| H26 | 0.5954 | 1.0000 | 0.8617 | 0.024* | |
| C27 | 0.5177 (4) | 1.06564 (14) | 0.73883 (13) | 0.0225 (4) | |
| H27 | 0.6577 | 1.1034 | 0.7251 | 0.027* | |
| C28 | 0.3492 (4) | 1.07231 (13) | 0.67788 (13) | 0.0210 (4) | |
| H28 | 0.3721 | 1.1154 | 0.6229 | 0.025* | |
| C29 | 0.1478 (4) | 1.01618 (14) | 0.69714 (13) | 0.0215 (4) | |
| H29 | 0.0333 | 1.0210 | 0.6551 | 0.026* | |
| C30 | 0.1120 (4) | 0.95307 (13) | 0.77718 (12) | 0.0185 (4) | |
| H30 | −0.0240 | 0.9138 | 0.7903 | 0.022* | |
| H1O | 1.110 (6) | 0.7524 (18) | 0.427 (2) | 0.057 (10)* | |
| H4O | 0.165 (6) | 0.752 (2) | 0.8385 (17) | 0.043 (8)* | |
| H2N | 0.657 (2) | 0.5927 (17) | 0.4337 (16) | 0.025 (6)* | |
| H4N | 0.600 (2) | 0.8017 (16) | 0.9621 (16) | 0.022 (6)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0143 (2) | 0.0138 (2) | 0.0141 (2) | −0.00056 (16) | −0.00083 (16) | −0.00670 (17) |
| S2 | 0.0133 (2) | 0.0169 (2) | 0.0150 (2) | −0.00203 (16) | −0.00012 (16) | −0.00687 (18) |
| O1 | 0.0216 (7) | 0.0193 (7) | 0.0200 (7) | −0.0062 (6) | 0.0044 (5) | −0.0098 (6) |
| O2 | 0.0157 (6) | 0.0183 (7) | 0.0186 (7) | −0.0004 (5) | −0.0014 (5) | −0.0068 (6) |
| O3 | 0.0213 (7) | 0.0173 (7) | 0.0206 (7) | −0.0016 (5) | −0.0016 (5) | −0.0103 (6) |
| O4 | 0.0222 (7) | 0.0268 (8) | 0.0248 (8) | 0.0032 (6) | −0.0080 (6) | −0.0140 (7) |
| O5 | 0.0145 (6) | 0.0248 (7) | 0.0205 (7) | −0.0042 (5) | 0.0008 (5) | −0.0080 (6) |
| O6 | 0.0217 (7) | 0.0225 (7) | 0.0175 (7) | −0.0013 (6) | −0.0007 (5) | −0.0117 (6) |
| N1 | 0.0181 (8) | 0.0142 (7) | 0.0152 (7) | −0.0022 (6) | −0.0020 (6) | −0.0078 (6) |
| N2 | 0.0160 (7) | 0.0160 (8) | 0.0157 (7) | −0.0036 (6) | 0.0015 (6) | −0.0091 (6) |
| N3 | 0.0169 (7) | 0.0173 (8) | 0.0162 (8) | −0.0034 (6) | −0.0004 (6) | −0.0084 (6) |
| N4 | 0.0152 (7) | 0.0167 (8) | 0.0166 (8) | −0.0014 (6) | −0.0026 (6) | −0.0080 (6) |
| C1 | 0.0182 (9) | 0.0153 (9) | 0.0140 (8) | 0.0000 (7) | −0.0023 (7) | −0.0049 (7) |
| C2 | 0.0217 (9) | 0.0157 (9) | 0.0205 (9) | −0.0026 (7) | −0.0030 (7) | −0.0060 (8) |
| C3 | 0.0239 (10) | 0.0169 (9) | 0.0230 (10) | 0.0006 (7) | −0.0065 (8) | −0.0110 (8) |
| C4 | 0.0207 (9) | 0.0191 (9) | 0.0175 (9) | 0.0042 (7) | −0.0052 (7) | −0.0093 (8) |
| C5 | 0.0178 (9) | 0.0168 (9) | 0.0170 (9) | 0.0005 (7) | −0.0023 (7) | −0.0074 (7) |
| C6 | 0.0182 (9) | 0.0131 (8) | 0.0132 (8) | 0.0004 (7) | −0.0028 (7) | −0.0053 (7) |
| C7 | 0.0257 (10) | 0.0265 (11) | 0.0271 (11) | 0.0034 (8) | −0.0021 (8) | −0.0181 (9) |
| C8 | 0.0164 (8) | 0.0135 (8) | 0.0132 (8) | 0.0003 (7) | −0.0024 (7) | −0.0039 (7) |
| C9 | 0.0233 (10) | 0.0181 (9) | 0.0222 (10) | −0.0051 (8) | 0.0081 (8) | −0.0102 (8) |
| C10 | 0.0165 (8) | 0.0164 (9) | 0.0127 (8) | −0.0003 (7) | 0.0000 (7) | −0.0064 (7) |
| C11 | 0.0212 (9) | 0.0202 (10) | 0.0191 (9) | −0.0035 (7) | −0.0014 (7) | −0.0091 (8) |
| C12 | 0.0230 (10) | 0.0260 (10) | 0.0169 (9) | 0.0012 (8) | −0.0050 (7) | −0.0101 (8) |
| C13 | 0.0272 (10) | 0.0219 (10) | 0.0145 (9) | 0.0026 (8) | 0.0006 (8) | −0.0057 (8) |
| C14 | 0.0290 (11) | 0.0181 (10) | 0.0225 (10) | −0.0055 (8) | −0.0002 (8) | −0.0061 (8) |
| C15 | 0.0217 (9) | 0.0210 (10) | 0.0189 (9) | −0.0029 (8) | −0.0018 (7) | −0.0086 (8) |
| C16 | 0.0186 (9) | 0.0218 (10) | 0.0176 (9) | −0.0035 (7) | 0.0003 (7) | −0.0085 (8) |
| C17 | 0.0219 (10) | 0.0283 (11) | 0.0197 (10) | −0.0052 (8) | −0.0019 (8) | −0.0111 (9) |
| C18 | 0.0270 (10) | 0.0257 (10) | 0.0177 (9) | −0.0087 (8) | 0.0045 (8) | −0.0124 (8) |
| C19 | 0.0213 (9) | 0.0221 (10) | 0.0208 (10) | −0.0073 (8) | 0.0050 (8) | −0.0105 (8) |
| C20 | 0.0197 (9) | 0.0197 (9) | 0.0181 (9) | −0.0039 (7) | 0.0011 (7) | −0.0091 (8) |
| C21 | 0.0177 (9) | 0.0190 (9) | 0.0157 (9) | −0.0050 (7) | 0.0017 (7) | −0.0083 (8) |
| C22 | 0.0288 (11) | 0.0269 (11) | 0.0325 (12) | −0.0031 (9) | 0.0015 (9) | −0.0188 (10) |
| C23 | 0.0161 (9) | 0.0169 (9) | 0.0138 (8) | −0.0040 (7) | 0.0009 (7) | −0.0049 (7) |
| C24 | 0.0206 (9) | 0.0177 (9) | 0.0191 (9) | −0.0008 (7) | −0.0034 (7) | −0.0070 (8) |
| C25 | 0.0167 (9) | 0.0146 (8) | 0.0136 (8) | 0.0002 (7) | 0.0003 (7) | −0.0047 (7) |
| C26 | 0.0182 (9) | 0.0200 (9) | 0.0209 (10) | −0.0019 (7) | −0.0025 (7) | −0.0075 (8) |
| C27 | 0.0191 (9) | 0.0174 (9) | 0.0262 (11) | −0.0029 (7) | 0.0015 (8) | −0.0054 (8) |
| C28 | 0.0235 (10) | 0.0184 (9) | 0.0180 (9) | 0.0028 (8) | 0.0017 (7) | −0.0060 (8) |
| C29 | 0.0243 (10) | 0.0233 (10) | 0.0188 (9) | 0.0019 (8) | −0.0038 (8) | −0.0115 (8) |
| C30 | 0.0184 (9) | 0.0195 (9) | 0.0192 (9) | −0.0012 (7) | −0.0018 (7) | −0.0099 (8) |
| S1—O3 | 1.4303 (14) | C11—C12 | 1.387 (3) |
| S1—O2 | 1.4360 (14) | C11—H11 | 0.9500 |
| S1—N2 | 1.6455 (16) | C12—C13 | 1.390 (3) |
| S1—C10 | 1.7603 (19) | C12—H12 | 0.9500 |
| S2—O6 | 1.4296 (14) | C13—C14 | 1.385 (3) |
| S2—O5 | 1.4355 (14) | C13—H13 | 0.9500 |
| S2—N4 | 1.6526 (17) | C14—C15 | 1.391 (3) |
| S2—C25 | 1.7591 (19) | C14—H14 | 0.9500 |
| O1—C1 | 1.364 (2) | C15—H15 | 0.9500 |
| O1—H1O | 0.84 (3) | C16—C17 | 1.394 (3) |
| O4—C16 | 1.355 (2) | C16—C21 | 1.419 (3) |
| O4—H4O | 0.85 (3) | C17—C18 | 1.376 (3) |
| N1—C8 | 1.295 (2) | C17—H17 | 0.9500 |
| N1—N2 | 1.401 (2) | C18—C19 | 1.399 (3) |
| N2—H2N | 0.879 (10) | C18—H18 | 0.9500 |
| N3—C23 | 1.290 (3) | C19—C20 | 1.389 (3) |
| N3—N4 | 1.408 (2) | C19—C22 | 1.508 (3) |
| N4—H4N | 0.877 (10) | C20—C21 | 1.405 (3) |
| C1—C2 | 1.389 (3) | C20—H20 | 0.9500 |
| C1—C6 | 1.416 (3) | C21—C23 | 1.478 (3) |
| C2—C3 | 1.384 (3) | C22—H22A | 0.9800 |
| C2—H2 | 0.9500 | C22—H22B | 0.9800 |
| C3—C4 | 1.392 (3) | C22—H22C | 0.9800 |
| C3—H3 | 0.9500 | C23—C24 | 1.500 (3) |
| C4—C5 | 1.390 (3) | C24—H24A | 0.9800 |
| C4—C7 | 1.511 (3) | C24—H24B | 0.9800 |
| C5—C6 | 1.406 (3) | C24—H24C | 0.9800 |
| C5—H5 | 0.9500 | C25—C30 | 1.389 (3) |
| C6—C8 | 1.479 (2) | C25—C26 | 1.393 (3) |
| C7—H7A | 0.9800 | C26—C27 | 1.387 (3) |
| C7—H7B | 0.9800 | C26—H26 | 0.9500 |
| C7—H7C | 0.9800 | C27—C28 | 1.388 (3) |
| C8—C9 | 1.495 (3) | C27—H27 | 0.9500 |
| C9—H9A | 0.9800 | C28—C29 | 1.386 (3) |
| C9—H9B | 0.9800 | C28—H28 | 0.9500 |
| C9—H9C | 0.9800 | C29—C30 | 1.386 (3) |
| C10—C15 | 1.387 (3) | C29—H29 | 0.9500 |
| C10—C11 | 1.391 (3) | C30—H30 | 0.9500 |
| O3—S1—O2 | 120.83 (8) | C11—C12—H12 | 119.9 |
| O3—S1—N2 | 104.70 (8) | C13—C12—H12 | 119.9 |
| O2—S1—N2 | 106.84 (8) | C14—C13—C12 | 120.07 (19) |
| O3—S1—C10 | 108.61 (9) | C14—C13—H13 | 120.0 |
| O2—S1—C10 | 107.30 (9) | C12—C13—H13 | 120.0 |
| N2—S1—C10 | 107.97 (9) | C13—C14—C15 | 120.38 (19) |
| O6—S2—O5 | 120.70 (9) | C13—C14—H14 | 119.8 |
| O6—S2—N4 | 104.46 (8) | C15—C14—H14 | 119.8 |
| O5—S2—N4 | 106.50 (9) | C10—C15—C14 | 118.93 (18) |
| O6—S2—C25 | 109.14 (9) | C10—C15—H15 | 120.5 |
| O5—S2—C25 | 107.40 (9) | C14—C15—H15 | 120.5 |
| N4—S2—C25 | 108.03 (9) | O4—C16—C17 | 117.22 (18) |
| C1—O1—H1O | 104 (3) | O4—C16—C21 | 122.92 (17) |
| C16—O4—H4O | 105 (2) | C17—C16—C21 | 119.85 (19) |
| C8—N1—N2 | 118.12 (16) | C18—C17—C16 | 120.71 (19) |
| N1—N2—S1 | 112.74 (12) | C18—C17—H17 | 119.6 |
| N1—N2—H2N | 118.6 (17) | C16—C17—H17 | 119.6 |
| S1—N2—H2N | 110.1 (17) | C17—C18—C19 | 121.38 (18) |
| C23—N3—N4 | 118.41 (16) | C17—C18—H18 | 119.3 |
| N3—N4—S2 | 111.80 (12) | C19—C18—H18 | 119.3 |
| N3—N4—H4N | 115.8 (17) | C20—C19—C18 | 117.66 (19) |
| S2—N4—H4N | 110.0 (17) | C20—C19—C22 | 121.06 (19) |
| O1—C1—C2 | 117.07 (17) | C18—C19—C22 | 121.29 (18) |
| O1—C1—C6 | 123.00 (17) | C19—C20—C21 | 123.01 (18) |
| C2—C1—C6 | 119.92 (18) | C19—C20—H20 | 118.5 |
| C3—C2—C1 | 120.50 (19) | C21—C20—H20 | 118.5 |
| C3—C2—H2 | 119.8 | C20—C21—C16 | 117.39 (17) |
| C1—C2—H2 | 119.8 | C20—C21—C23 | 120.48 (17) |
| C2—C3—C4 | 121.39 (18) | C16—C21—C23 | 122.13 (18) |
| C2—C3—H3 | 119.3 | C19—C22—H22A | 109.5 |
| C4—C3—H3 | 119.3 | C19—C22—H22B | 109.5 |
| C5—C4—C3 | 117.86 (18) | H22A—C22—H22B | 109.5 |
| C5—C4—C7 | 120.74 (19) | C19—C22—H22C | 109.5 |
| C3—C4—C7 | 121.40 (18) | H22A—C22—H22C | 109.5 |
| C4—C5—C6 | 122.59 (19) | H22B—C22—H22C | 109.5 |
| C4—C5—H5 | 118.7 | N3—C23—C21 | 115.90 (17) |
| C6—C5—H5 | 118.7 | N3—C23—C24 | 123.93 (17) |
| C5—C6—C1 | 117.73 (17) | C21—C23—C24 | 120.16 (17) |
| C5—C6—C8 | 120.05 (17) | C23—C24—H24A | 109.5 |
| C1—C6—C8 | 122.22 (17) | C23—C24—H24B | 109.5 |
| C4—C7—H7A | 109.5 | H24A—C24—H24B | 109.5 |
| C4—C7—H7B | 109.5 | C23—C24—H24C | 109.5 |
| H7A—C7—H7B | 109.5 | H24A—C24—H24C | 109.5 |
| C4—C7—H7C | 109.5 | H24B—C24—H24C | 109.5 |
| H7A—C7—H7C | 109.5 | C30—C25—C26 | 121.68 (18) |
| H7B—C7—H7C | 109.5 | C30—C25—S2 | 120.18 (15) |
| N1—C8—C6 | 115.73 (17) | C26—C25—S2 | 118.14 (15) |
| N1—C8—C9 | 123.48 (17) | C27—C26—C25 | 118.62 (18) |
| C6—C8—C9 | 120.75 (16) | C27—C26—H26 | 120.7 |
| C8—C9—H9A | 109.5 | C25—C26—H26 | 120.7 |
| C8—C9—H9B | 109.5 | C26—C27—C28 | 120.36 (19) |
| H9A—C9—H9B | 109.5 | C26—C27—H27 | 119.8 |
| C8—C9—H9C | 109.5 | C28—C27—H27 | 119.8 |
| H9A—C9—H9C | 109.5 | C29—C28—C27 | 120.14 (19) |
| H9B—C9—H9C | 109.5 | C29—C28—H28 | 119.9 |
| C15—C10—C11 | 121.32 (18) | C27—C28—H28 | 119.9 |
| C15—C10—S1 | 120.15 (14) | C30—C29—C28 | 120.52 (19) |
| C11—C10—S1 | 118.53 (15) | C30—C29—H29 | 119.7 |
| C12—C11—C10 | 119.01 (19) | C28—C29—H29 | 119.7 |
| C12—C11—H11 | 120.5 | C29—C30—C25 | 118.66 (18) |
| C10—C11—H11 | 120.5 | C29—C30—H30 | 120.7 |
| C11—C12—C13 | 120.27 (18) | C25—C30—H30 | 120.7 |
| C8—N1—N2—S1 | −178.55 (13) | C12—C13—C14—C15 | −0.4 (3) |
| O3—S1—N2—N1 | 178.10 (12) | C11—C10—C15—C14 | −0.5 (3) |
| O2—S1—N2—N1 | 48.83 (14) | S1—C10—C15—C14 | 179.65 (16) |
| C10—S1—N2—N1 | −66.31 (14) | C13—C14—C15—C10 | 0.6 (3) |
| C23—N3—N4—S2 | −178.21 (14) | O4—C16—C17—C18 | −179.93 (19) |
| O6—S2—N4—N3 | −178.19 (12) | C21—C16—C17—C18 | −0.3 (3) |
| O5—S2—N4—N3 | 53.04 (14) | C16—C17—C18—C19 | −0.3 (3) |
| C25—S2—N4—N3 | −62.08 (14) | C17—C18—C19—C20 | 0.2 (3) |
| O1—C1—C2—C3 | 179.06 (17) | C17—C18—C19—C22 | −179.9 (2) |
| C6—C1—C2—C3 | −0.5 (3) | C18—C19—C20—C21 | 0.4 (3) |
| C1—C2—C3—C4 | 0.2 (3) | C22—C19—C20—C21 | −179.54 (19) |
| C2—C3—C4—C5 | 0.4 (3) | C19—C20—C21—C16 | −0.9 (3) |
| C2—C3—C4—C7 | 179.82 (18) | C19—C20—C21—C23 | −179.97 (18) |
| C3—C4—C5—C6 | −0.8 (3) | O4—C16—C21—C20 | −179.57 (18) |
| C7—C4—C5—C6 | 179.81 (18) | C17—C16—C21—C20 | 0.8 (3) |
| C4—C5—C6—C1 | 0.5 (3) | O4—C16—C21—C23 | −0.5 (3) |
| C4—C5—C6—C8 | −179.50 (17) | C17—C16—C21—C23 | 179.88 (18) |
| O1—C1—C6—C5 | −179.38 (17) | N4—N3—C23—C21 | 178.11 (16) |
| C2—C1—C6—C5 | 0.1 (3) | N4—N3—C23—C24 | −0.7 (3) |
| O1—C1—C6—C8 | 0.6 (3) | C20—C21—C23—N3 | 176.27 (18) |
| C2—C1—C6—C8 | −179.87 (17) | C16—C21—C23—N3 | −2.8 (3) |
| N2—N1—C8—C6 | 176.62 (15) | C20—C21—C23—C24 | −4.9 (3) |
| N2—N1—C8—C9 | −1.1 (3) | C16—C21—C23—C24 | 176.08 (18) |
| C5—C6—C8—N1 | 177.95 (17) | O6—S2—C25—C30 | −147.06 (15) |
| C1—C6—C8—N1 | −2.0 (3) | O5—S2—C25—C30 | −14.60 (18) |
| C5—C6—C8—C9 | −4.2 (3) | N4—S2—C25—C30 | 99.92 (16) |
| C1—C6—C8—C9 | 175.76 (18) | O6—S2—C25—C26 | 31.95 (18) |
| O3—S1—C10—C15 | −151.83 (16) | O5—S2—C25—C26 | 164.42 (15) |
| O2—S1—C10—C15 | −19.67 (18) | N4—S2—C25—C26 | −81.06 (17) |
| N2—S1—C10—C15 | 95.17 (17) | C30—C25—C26—C27 | 0.1 (3) |
| O3—S1—C10—C11 | 28.32 (18) | S2—C25—C26—C27 | −178.86 (16) |
| O2—S1—C10—C11 | 160.48 (15) | C25—C26—C27—C28 | 1.2 (3) |
| N2—S1—C10—C11 | −84.68 (16) | C26—C27—C28—C29 | −1.3 (3) |
| C15—C10—C11—C12 | 0.3 (3) | C27—C28—C29—C30 | 0.1 (3) |
| S1—C10—C11—C12 | −179.87 (15) | C28—C29—C30—C25 | 1.2 (3) |
| C10—C11—C12—C13 | −0.1 (3) | C26—C25—C30—C29 | −1.3 (3) |
| C11—C12—C13—C14 | 0.2 (3) | S2—C25—C30—C29 | 177.65 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1o···N1 | 0.84 (3) | 1.80 (2) | 2.562 (2) | 151 (4) |
| O4—H4o···N3 | 0.85 (3) | 1.79 (2) | 2.563 (2) | 150 (3) |
| N2—H2n···O2i | 0.88 (1) | 2.18 (1) | 3.040 (2) | 168 (2) |
| N4—H4n···O5ii | 0.88 (1) | 2.07 (1) | 2.942 (2) | 173 (2) |
| Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1o···N1 | 0.84 (3) | 1.80 (2) | 2.562 (2) | 151 (4) |
| O4—H4o···N3 | 0.85 (3) | 1.79 (2) | 2.563 (2) | 150 (3) |
| N2—H2n···O2i | 0.88 (1) | 2.18 (1) | 3.040 (2) | 168 (2) |
| N4—H4n···O5ii | 0.88 (1) | 2.07 (1) | 2.942 (2) | 173 (2) |
| Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.
Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2008). publCIF. In preparation.
2'-(2-Hydroxyphenyl-1-ethylidene)benzenesulfonohydrazide adopts a hydrogen-bonded chain structure; the chain runs along the a-axis of the monoclinic unit cell and the repeat distance is the length of the this axis, i.e., 5.18 Å (Ali et al., 2007). An additional methyl group in the molecule (Scheme I) does not result in any significant difference in both structure and packing (Fig. 1). The two independent molecules are each linked by an N–H···O sulfonyl hydrogen-bond into a linear chain that runs along the shortest axis of the triclinic unit cell; the repeat distance is 5.15 Å. The hydroxy groups are engaged in intramolecular hydrogen bonding (Table 1.).