In the title compound, C
13H
12N
2O
4S, the dihedral angle between the two aromatic rings is 89.5 (1)°. In the crystal structure, molecules are linked by O—H

O
hydroxy and N—H

O
sulfonyl hydrogen bonds, forming a ribbon that propagates along the
b axis; there is also an intramolecular O—H

N hydrogen bond.
Supporting information
CCDC reference: 677650
Key indicators
- Single-crystal X-ray study
- T = 128 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.104
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Benzenesulfohydrazine (0.29 g, 1.7 mmol) and 2,5-dihydroxybenzaldehyde (0.24 g,
1.7 mmol) were refluxed in ethanol (50 ml) for 2 h. The solvent was removed to
give the product Schiff base, and crystals were obtained upon
recrystallization from ethanol.
All hydrogen atoms were located in difference Fourier maps. Those bonded to C
were restrained to 0.95±0.01 Å, and those bonded to N or O to 0.85±0.01 Å. All displacement parameters were freely refined.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).
N'-(2,5-Dihydroxybenzylidene)benzenesulfonohydrazide
top
Crystal data top
C13H12N2O4S | F(000) = 608 |
Mr = 292.31 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9918 reflections |
a = 12.5814 (2) Å | θ = 5.0–63.2° |
b = 7.1601 (1) Å | µ = 0.27 mm−1 |
c = 14.6727 (2) Å | T = 128 K |
β = 105.540 (1)° | Block, yellow |
V = 1273.46 (3) Å3 | 0.65 × 0.33 × 0.29 mm |
Z = 4 | |
Data collection top
Bruker APEXII diffractometer | 2684 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
ϕ and ω scans | h = −16→16 |
16406 measured reflections | k = −9→9 |
2924 independent reflections | l = −18→19 |
Refinement top
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0666P)2 + 0.482P] where P = (Fo2 + 2Fc2)/3 |
2924 reflections | (Δ/σ)max = 0.001 |
229 parameters | Δρmax = 0.40 e Å−3 |
11 restraints | Δρmin = −0.35 e Å−3 |
Crystal data top
C13H12N2O4S | V = 1273.46 (3) Å3 |
Mr = 292.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.5814 (2) Å | µ = 0.27 mm−1 |
b = 7.1601 (1) Å | T = 128 K |
c = 14.6727 (2) Å | 0.65 × 0.33 × 0.29 mm |
β = 105.540 (1)° | |
Data collection top
Bruker APEXII diffractometer | 2684 reflections with I > 2σ(I) |
16406 measured reflections | Rint = 0.023 |
2924 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 11 restraints |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.40 e Å−3 |
2924 reflections | Δρmin = −0.35 e Å−3 |
229 parameters | |
Special details top
Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to
measure the somewhat large crystal. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.77742 (3) | 0.75958 (4) | 0.66733 (2) | 0.01720 (12) | |
N1 | 0.83576 (9) | 0.55528 (16) | 0.65868 (8) | 0.0190 (2) | |
N2 | 0.84430 (9) | 0.52079 (16) | 0.56754 (8) | 0.0186 (2) | |
O1 | 0.77923 (9) | 0.76844 (15) | 0.76588 (7) | 0.0245 (2) | |
O2 | 0.83351 (8) | 0.89724 (14) | 0.62689 (7) | 0.0249 (2) | |
O3 | 0.85080 (9) | 0.64124 (14) | 0.40471 (7) | 0.0276 (2) | |
O4 | 0.91487 (10) | −0.08605 (15) | 0.30407 (8) | 0.0307 (3) | |
C1 | 0.63909 (11) | 0.74943 (17) | 0.59938 (9) | 0.0164 (3) | |
C2 | 0.61433 (11) | 0.7976 (2) | 0.50377 (9) | 0.0198 (3) | |
C3 | 0.50524 (12) | 0.7887 (2) | 0.44977 (10) | 0.0228 (3) | |
C4 | 0.42314 (12) | 0.7347 (2) | 0.49182 (11) | 0.0241 (3) | |
C5 | 0.44840 (12) | 0.6872 (2) | 0.58702 (11) | 0.0242 (3) | |
C6 | 0.55757 (11) | 0.69292 (19) | 0.64210 (9) | 0.0204 (3) | |
C7 | 0.86202 (10) | 0.35212 (19) | 0.54498 (9) | 0.0182 (3) | |
C8 | 0.87129 (10) | 0.31449 (19) | 0.44957 (9) | 0.0175 (3) | |
C9 | 0.88699 (11) | 0.12938 (19) | 0.42327 (10) | 0.0199 (3) | |
C10 | 0.89662 (11) | 0.08955 (19) | 0.33332 (10) | 0.0220 (3) | |
C11 | 0.88899 (13) | 0.2343 (2) | 0.26805 (10) | 0.0248 (3) | |
C12 | 0.87375 (12) | 0.4168 (2) | 0.29252 (10) | 0.0248 (3) | |
C13 | 0.86505 (11) | 0.45797 (19) | 0.38301 (9) | 0.0203 (3) | |
H3O | 0.8478 (19) | 0.650 (3) | 0.4615 (8) | 0.052 (6)* | |
H4O | 0.8920 (18) | −0.168 (3) | 0.3363 (15) | 0.050 (6)* | |
H1N | 0.8083 (15) | 0.470 (2) | 0.6862 (13) | 0.034 (5)* | |
H2 | 0.6718 (11) | 0.834 (2) | 0.4758 (12) | 0.026 (4)* | |
H3 | 0.4885 (15) | 0.824 (3) | 0.3850 (7) | 0.031 (5)* | |
H4 | 0.3471 (18) | 0.729 (3) | 0.4543 (14) | 0.033 (5)* | |
H5 | 0.3922 (12) | 0.651 (3) | 0.6166 (12) | 0.032 (5)* | |
H6 | 0.5728 (13) | 0.657 (2) | 0.7068 (7) | 0.024 (4)* | |
H7 | 0.8721 (15) | 0.2494 (17) | 0.5872 (10) | 0.019 (4)* | |
H9 | 0.8924 (15) | 0.031 (2) | 0.4681 (10) | 0.028 (4)* | |
H11 | 0.8879 (18) | 0.201 (3) | 0.2057 (8) | 0.045 (6)* | |
H12 | 0.8656 (15) | 0.515 (2) | 0.2476 (11) | 0.032 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01696 (19) | 0.01935 (18) | 0.01461 (19) | −0.00098 (10) | 0.00306 (13) | −0.00294 (10) |
N1 | 0.0212 (5) | 0.0213 (5) | 0.0157 (5) | 0.0023 (4) | 0.0070 (4) | 0.0008 (4) |
N2 | 0.0174 (5) | 0.0235 (6) | 0.0161 (5) | 0.0000 (4) | 0.0066 (4) | −0.0005 (4) |
O1 | 0.0261 (5) | 0.0312 (6) | 0.0144 (5) | 0.0025 (4) | 0.0025 (4) | −0.0053 (4) |
O2 | 0.0229 (5) | 0.0226 (5) | 0.0288 (5) | −0.0048 (4) | 0.0065 (4) | −0.0010 (4) |
O3 | 0.0434 (6) | 0.0195 (5) | 0.0232 (5) | 0.0037 (4) | 0.0147 (5) | 0.0033 (4) |
O4 | 0.0461 (7) | 0.0225 (5) | 0.0318 (6) | −0.0037 (4) | 0.0249 (5) | −0.0047 (4) |
C1 | 0.0166 (6) | 0.0173 (6) | 0.0150 (6) | 0.0003 (4) | 0.0037 (5) | −0.0022 (4) |
C2 | 0.0210 (6) | 0.0231 (6) | 0.0164 (6) | 0.0009 (5) | 0.0069 (5) | −0.0010 (5) |
C3 | 0.0235 (7) | 0.0274 (7) | 0.0163 (6) | 0.0028 (5) | 0.0033 (5) | −0.0013 (5) |
C4 | 0.0187 (7) | 0.0266 (7) | 0.0247 (7) | −0.0007 (5) | 0.0020 (6) | −0.0034 (5) |
C5 | 0.0208 (6) | 0.0255 (7) | 0.0281 (7) | −0.0030 (5) | 0.0097 (5) | −0.0006 (6) |
C6 | 0.0225 (6) | 0.0219 (6) | 0.0176 (6) | −0.0010 (5) | 0.0069 (5) | 0.0010 (5) |
C7 | 0.0162 (6) | 0.0214 (6) | 0.0175 (6) | 0.0003 (5) | 0.0054 (5) | 0.0018 (5) |
C8 | 0.0148 (6) | 0.0219 (6) | 0.0167 (6) | 0.0003 (5) | 0.0058 (4) | 0.0011 (5) |
C9 | 0.0200 (6) | 0.0207 (6) | 0.0211 (6) | 0.0002 (5) | 0.0091 (5) | 0.0018 (5) |
C10 | 0.0220 (6) | 0.0220 (6) | 0.0253 (7) | −0.0025 (5) | 0.0118 (5) | −0.0027 (5) |
C11 | 0.0286 (7) | 0.0300 (7) | 0.0187 (7) | −0.0033 (5) | 0.0116 (6) | −0.0017 (5) |
C12 | 0.0298 (7) | 0.0260 (7) | 0.0201 (7) | −0.0009 (6) | 0.0095 (5) | 0.0051 (5) |
C13 | 0.0202 (6) | 0.0200 (6) | 0.0214 (7) | 0.0011 (5) | 0.0071 (5) | 0.0010 (5) |
Geometric parameters (Å, º) top
S1—O2 | 1.4304 (10) | C4—C5 | 1.389 (2) |
S1—O1 | 1.4415 (10) | C4—H4 | 0.97 (2) |
S1—N1 | 1.6567 (12) | C5—C6 | 1.395 (2) |
S1—C1 | 1.7602 (13) | C5—H5 | 0.959 (9) |
N1—N2 | 1.3920 (15) | C6—H6 | 0.953 (9) |
N1—H1N | 0.85 (1) | C7—C8 | 1.4607 (17) |
N2—C7 | 1.2874 (17) | C7—H7 | 0.948 (9) |
O3—C13 | 1.3733 (16) | C8—C13 | 1.4051 (18) |
O3—H3O | 0.85 (1) | C8—C9 | 1.4090 (18) |
O4—C10 | 1.3677 (16) | C9—C10 | 1.3870 (19) |
O4—H4O | 0.85 (1) | C9—H9 | 0.953 (9) |
C1—C2 | 1.3963 (18) | C10—C11 | 1.397 (2) |
C1—C6 | 1.3976 (18) | C11—C12 | 1.382 (2) |
C2—C3 | 1.3904 (19) | C11—H11 | 0.943 (9) |
C2—H2 | 0.958 (9) | C12—C13 | 1.3928 (19) |
C3—C4 | 1.392 (2) | C12—H12 | 0.950 (9) |
C3—H3 | 0.951 (9) | | |
| | | |
O2—S1—O1 | 120.59 (6) | C6—C5—H5 | 118.4 (11) |
O2—S1—N1 | 107.38 (6) | C5—C6—C1 | 118.40 (12) |
O1—S1—N1 | 103.14 (6) | C5—C6—H6 | 118.2 (10) |
O2—S1—C1 | 108.44 (6) | C1—C6—H6 | 123.4 (10) |
O1—S1—C1 | 108.51 (6) | N2—C7—C8 | 118.90 (12) |
N1—S1—C1 | 108.14 (6) | N2—C7—H7 | 124.2 (10) |
N2—N1—S1 | 112.33 (9) | C8—C7—H7 | 116.9 (10) |
N2—N1—H1N | 118.3 (13) | C13—C8—C9 | 118.90 (12) |
S1—N1—H1N | 110.4 (13) | C13—C8—C7 | 121.83 (12) |
C7—N2—N1 | 118.47 (11) | C9—C8—C7 | 119.28 (12) |
C13—O3—H3O | 110.2 (17) | C10—C9—C8 | 120.55 (12) |
C10—O4—H4O | 110.5 (16) | C10—C9—H9 | 119.8 (11) |
C2—C1—C6 | 121.94 (12) | C8—C9—H9 | 119.6 (11) |
C2—C1—S1 | 118.65 (10) | O4—C10—C9 | 123.53 (13) |
C6—C1—S1 | 119.40 (10) | O4—C10—C11 | 116.96 (12) |
C3—C2—C1 | 118.80 (12) | C9—C10—C11 | 119.50 (13) |
C3—C2—H2 | 120.7 (11) | C12—C11—C10 | 120.81 (13) |
C1—C2—H2 | 120.5 (11) | C12—C11—H11 | 121.8 (14) |
C2—C3—C4 | 119.77 (13) | C10—C11—H11 | 117.1 (14) |
C2—C3—H3 | 118.6 (11) | C11—C12—C13 | 119.98 (13) |
C4—C3—H3 | 121.6 (11) | C11—C12—H12 | 121.0 (12) |
C5—C4—C3 | 121.10 (13) | C13—C12—H12 | 118.9 (12) |
C5—C4—H4 | 119.2 (12) | O3—C13—C12 | 118.16 (12) |
C3—C4—H4 | 119.7 (12) | O3—C13—C8 | 121.59 (12) |
C4—C5—C6 | 119.98 (13) | C12—C13—C8 | 120.25 (12) |
C4—C5—H5 | 121.6 (11) | | |
| | | |
O2—S1—N1—N2 | −50.34 (10) | S1—C1—C6—C5 | 179.56 (10) |
O1—S1—N1—N2 | −178.71 (8) | N1—N2—C7—C8 | −179.90 (10) |
C1—S1—N1—N2 | 66.48 (10) | N2—C7—C8—C13 | 2.14 (19) |
S1—N1—N2—C7 | −163.01 (10) | N2—C7—C8—C9 | −177.89 (12) |
O2—S1—C1—C2 | 27.78 (12) | C13—C8—C9—C10 | 0.28 (19) |
O1—S1—C1—C2 | 160.41 (10) | C7—C8—C9—C10 | −179.68 (12) |
N1—S1—C1—C2 | −88.36 (11) | C8—C9—C10—O4 | 178.20 (12) |
O2—S1—C1—C6 | −152.52 (10) | C8—C9—C10—C11 | −1.0 (2) |
O1—S1—C1—C6 | −19.89 (12) | O4—C10—C11—C12 | −178.16 (14) |
N1—S1—C1—C6 | 91.34 (11) | C9—C10—C11—C12 | 1.0 (2) |
C6—C1—C2—C3 | −0.1 (2) | C10—C11—C12—C13 | −0.5 (2) |
S1—C1—C2—C3 | 179.64 (10) | C11—C12—C13—O3 | 179.51 (13) |
C1—C2—C3—C4 | 0.8 (2) | C11—C12—C13—C8 | −0.2 (2) |
C2—C3—C4—C5 | −0.7 (2) | C9—C8—C13—O3 | −179.42 (12) |
C3—C4—C5—C6 | −0.1 (2) | C7—C8—C13—O3 | 0.5 (2) |
C4—C5—C6—C1 | 0.8 (2) | C9—C8—C13—C12 | 0.32 (19) |
C2—C1—C6—C5 | −0.8 (2) | C7—C8—C13—C12 | −179.71 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···N2 | 0.85 (1) | 1.82 (2) | 2.562 (2) | 145 (2) |
O4—H4O···O3i | 0.85 (1) | 1.85 (1) | 2.698 (2) | 175 (2) |
N1—H1N···O1ii | 0.85 (1) | 2.05 (1) | 2.897 (2) | 171 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y−1/2, −z+3/2. |
Experimental details
Crystal data |
Chemical formula | C13H12N2O4S |
Mr | 292.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 128 |
a, b, c (Å) | 12.5814 (2), 7.1601 (1), 14.6727 (2) |
β (°) | 105.540 (1) |
V (Å3) | 1273.46 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.65 × 0.33 × 0.29 |
|
Data collection |
Diffractometer | Bruker APEXII diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16406, 2924, 2684 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.104, 1.07 |
No. of reflections | 2924 |
No. of parameters | 229 |
No. of restraints | 11 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.40, −0.35 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···N2 | 0.85 (1) | 1.82 (2) | 2.562 (2) | 145 (2) |
O4—H4O···O3i | 0.85 (1) | 1.85 (1) | 2.698 (2) | 175 (2) |
N1—H1N···O1ii | 0.85 (1) | 2.05 (1) | 2.897 (2) | 171 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y−1/2, −z+3/2. |
A recent study reported the crystal structure of 2'-(5-bromo-2-hydroxybenzylidene)benzenesulfonohydrazide (Ali et al., 2007). A second hydroxy group is introduced in the title compound.