Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020065/hb2390sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020065/hb2390Isup2.hkl |
CCDC reference: 647713
Benzenesulfohydrazine (0.3 g, 2 mmol) and 5-methylindole-3-carbaldehyde (0.3 g, 2 mmol) were dissolved in ethanol (50 ml). The reactants were heated under reflux for 1 h. The solvent was removed to give the Schiff base, which was purified by recrystallzation from ethanol to yield faint yellow blocks of (I).
The carbon-bound H atoms were placed at calculated positions (C–H = 0.95–0.98 Å), and they were included in the refinement in the riding model approximation with U(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The N-bound H atoms were located in a difference Fourier map, and were refined with a distance restraint [N–H = 0.88 (1) Å]; their Uiso values were freely refined.
The crystal structure of 2'-(1H-indol-3-ylmethylene)benzenesulfonohydrazine consists of molecules that are linked by Namino–H···Osulfonoy and Nindolyl–H···Nimino hydrogen bonds into layers (Ali, Yusnita, Wan Jefrey & Ng, 2007; Ali, Yusnita & Ng, 2007). The presence of the methyl substituent in the 5-position of the indolyl portion leads to a similar layer structure for the title compound (I).
For related structures, see: Ali, Yusnita et al. (2007); Ali, Yusnita & Ng (2007).
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
Fig. 1. View of the molecular structure of (I). Displacement ellipsoids are drawn at the 70% probability level and H atoms are shown as spheres of arbitrary radius. |
C16H15N3O2S | F(000) = 1312 |
Mr = 313.37 | Dx = 1.314 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9953 reflections |
a = 13.3080 (2) Å | θ = 2.3–33.9° |
b = 10.0043 (1) Å | µ = 0.21 mm−1 |
c = 23.7968 (3) Å | T = 173 K |
V = 3168.24 (7) Å3 | Irregular block, faint yellow |
Z = 8 | 0.54 × 0.53 × 0.50 mm |
Bruker APEXII CCD diffractometer | 3334 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
φ and ω scans | h = −17→17 |
41089 measured reflections | k = −12→12 |
3637 independent reflections | l = −30→30 |
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: difmap and geom |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0598P)2 + 1.5134P] where P = (Fo2 + 2Fc2)/3 |
3637 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.34 e Å−3 |
2 restraints | Δρmin = −0.39 e Å−3 |
C16H15N3O2S | V = 3168.24 (7) Å3 |
Mr = 313.37 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.3080 (2) Å | µ = 0.21 mm−1 |
b = 10.0043 (1) Å | T = 173 K |
c = 23.7968 (3) Å | 0.54 × 0.53 × 0.50 mm |
Bruker APEXII CCD diffractometer | 3334 reflections with I > 2σ(I) |
41089 measured reflections | Rint = 0.025 |
3637 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | 2 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.34 e Å−3 |
3637 reflections | Δρmin = −0.39 e Å−3 |
208 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.23027 (2) | 0.11903 (3) | 0.421914 (12) | 0.01747 (10) | |
O1 | 0.21446 (7) | 0.25306 (8) | 0.40210 (4) | 0.0244 (2) | |
O2 | 0.14557 (6) | 0.04044 (9) | 0.43913 (4) | 0.0248 (2) | |
N1 | 0.27929 (7) | 0.03416 (10) | 0.36867 (4) | 0.0181 (2) | |
H1N | 0.2819 (13) | −0.0515 (10) | 0.3758 (7) | 0.035 (5)* | |
N2 | 0.37106 (7) | 0.09299 (10) | 0.35018 (4) | 0.0191 (2) | |
N3 | 0.64312 (8) | 0.08303 (12) | 0.23137 (4) | 0.0247 (2) | |
H3N | 0.6840 (12) | 0.0675 (19) | 0.2036 (6) | 0.046 (5)* | |
C1 | 0.32075 (9) | 0.12280 (11) | 0.47563 (5) | 0.0190 (2) | |
C2 | 0.32850 (10) | 0.01370 (13) | 0.51174 (5) | 0.0265 (3) | |
H2 | 0.2858 | −0.0617 | 0.5074 | 0.032* | |
C3 | 0.40021 (12) | 0.01753 (15) | 0.55427 (6) | 0.0342 (3) | |
H3 | 0.4063 | −0.0554 | 0.5796 | 0.041* | |
C4 | 0.46263 (12) | 0.12737 (15) | 0.55972 (6) | 0.0346 (3) | |
H4 | 0.5111 | 0.1294 | 0.5890 | 0.041* | |
C5 | 0.45525 (10) | 0.23442 (14) | 0.52298 (6) | 0.0299 (3) | |
H5 | 0.4990 | 0.3088 | 0.5269 | 0.036* | |
C6 | 0.38383 (9) | 0.23295 (12) | 0.48040 (5) | 0.0230 (2) | |
H6 | 0.3782 | 0.3059 | 0.4550 | 0.028* | |
C7 | 0.41556 (9) | 0.02655 (12) | 0.31144 (5) | 0.0211 (2) | |
H7 | 0.3866 | −0.0540 | 0.2979 | 0.025* | |
C8 | 0.50919 (9) | 0.07311 (12) | 0.28826 (5) | 0.0207 (2) | |
C9 | 0.55733 (10) | 0.01550 (13) | 0.24299 (5) | 0.0251 (3) | |
H9 | 0.5338 | −0.0604 | 0.2229 | 0.030* | |
C10 | 0.57019 (9) | 0.18475 (11) | 0.30554 (5) | 0.0190 (2) | |
C11 | 0.56175 (9) | 0.28304 (12) | 0.34724 (5) | 0.0210 (2) | |
H11 | 0.5058 | 0.2831 | 0.3720 | 0.025* | |
C12 | 0.63569 (10) | 0.38036 (13) | 0.35217 (5) | 0.0251 (3) | |
C13 | 0.72032 (10) | 0.37621 (13) | 0.31648 (6) | 0.0277 (3) | |
H13 | 0.7718 | 0.4411 | 0.3212 | 0.033* | |
C14 | 0.73080 (9) | 0.28053 (13) | 0.27478 (6) | 0.0258 (3) | |
H14 | 0.7880 | 0.2789 | 0.2509 | 0.031* | |
C15 | 0.65415 (9) | 0.18704 (12) | 0.26929 (5) | 0.0211 (2) | |
C16 | 0.62308 (12) | 0.49234 (16) | 0.39414 (7) | 0.0379 (3) | |
H16A | 0.5575 | 0.5349 | 0.3886 | 0.057* | |
H16B | 0.6764 | 0.5586 | 0.3887 | 0.057* | |
H16C | 0.6271 | 0.4562 | 0.4323 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01618 (16) | 0.01306 (16) | 0.02316 (17) | 0.00111 (9) | −0.00103 (10) | 0.00258 (10) |
O1 | 0.0252 (4) | 0.0141 (4) | 0.0339 (5) | 0.0034 (3) | −0.0041 (4) | 0.0049 (3) |
O2 | 0.0187 (4) | 0.0206 (4) | 0.0350 (5) | −0.0012 (3) | 0.0028 (3) | 0.0033 (4) |
N1 | 0.0188 (5) | 0.0137 (4) | 0.0218 (5) | −0.0015 (3) | −0.0007 (4) | 0.0017 (4) |
N2 | 0.0189 (5) | 0.0178 (5) | 0.0207 (5) | −0.0026 (4) | −0.0012 (4) | 0.0031 (4) |
N3 | 0.0255 (5) | 0.0275 (5) | 0.0213 (5) | 0.0030 (4) | 0.0038 (4) | −0.0028 (4) |
C1 | 0.0199 (5) | 0.0182 (5) | 0.0189 (5) | 0.0033 (4) | 0.0002 (4) | −0.0006 (4) |
C2 | 0.0303 (7) | 0.0240 (6) | 0.0253 (6) | 0.0022 (5) | 0.0004 (5) | 0.0045 (5) |
C3 | 0.0405 (8) | 0.0373 (8) | 0.0247 (6) | 0.0098 (6) | −0.0038 (6) | 0.0072 (5) |
C4 | 0.0333 (7) | 0.0449 (9) | 0.0254 (6) | 0.0097 (6) | −0.0091 (6) | −0.0064 (6) |
C5 | 0.0256 (6) | 0.0302 (7) | 0.0340 (7) | 0.0026 (5) | −0.0043 (5) | −0.0106 (5) |
C6 | 0.0230 (6) | 0.0188 (5) | 0.0271 (6) | 0.0027 (4) | −0.0007 (5) | −0.0031 (4) |
C7 | 0.0216 (5) | 0.0191 (5) | 0.0226 (5) | −0.0009 (4) | −0.0035 (4) | −0.0008 (4) |
C8 | 0.0219 (6) | 0.0202 (6) | 0.0200 (5) | 0.0014 (5) | −0.0014 (4) | −0.0010 (4) |
C9 | 0.0262 (6) | 0.0241 (6) | 0.0251 (6) | 0.0012 (5) | −0.0009 (5) | −0.0046 (5) |
C10 | 0.0204 (5) | 0.0182 (5) | 0.0183 (5) | 0.0024 (4) | −0.0007 (4) | 0.0030 (4) |
C11 | 0.0229 (6) | 0.0215 (6) | 0.0187 (5) | 0.0021 (5) | −0.0002 (4) | 0.0004 (4) |
C12 | 0.0273 (6) | 0.0227 (6) | 0.0252 (6) | 0.0001 (5) | −0.0028 (5) | −0.0021 (5) |
C13 | 0.0263 (6) | 0.0245 (6) | 0.0325 (7) | −0.0053 (5) | −0.0011 (5) | 0.0018 (5) |
C14 | 0.0234 (6) | 0.0271 (6) | 0.0269 (6) | −0.0002 (5) | 0.0035 (5) | 0.0041 (5) |
C15 | 0.0230 (6) | 0.0210 (6) | 0.0193 (5) | 0.0038 (5) | 0.0005 (4) | 0.0024 (4) |
C16 | 0.0369 (8) | 0.0349 (8) | 0.0418 (8) | −0.0054 (6) | −0.0011 (6) | −0.0160 (6) |
S1—O2 | 1.4340 (9) | C6—H6 | 0.9500 |
S1—O1 | 1.4369 (9) | C7—C8 | 1.4401 (17) |
S1—N1 | 1.6589 (10) | C7—H7 | 0.9500 |
S1—C1 | 1.7566 (12) | C8—C9 | 1.3794 (17) |
N1—N2 | 1.4253 (13) | C8—C10 | 1.4406 (17) |
N1—H1N | 0.874 (9) | C9—H9 | 0.9500 |
N2—C7 | 1.2816 (16) | C10—C11 | 1.4015 (16) |
N3—C9 | 1.3551 (17) | C10—C15 | 1.4119 (16) |
N3—C15 | 1.3851 (16) | C11—C12 | 1.3892 (18) |
N3—H3N | 0.870 (9) | C11—H11 | 0.9500 |
C1—C6 | 1.3899 (17) | C12—C13 | 1.4112 (19) |
C1—C2 | 1.3929 (17) | C12—C16 | 1.5101 (18) |
C2—C3 | 1.3914 (19) | C13—C14 | 1.3858 (19) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C4 | 1.384 (2) | C14—C15 | 1.3901 (18) |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.386 (2) | C16—H16A | 0.9800 |
C4—H4 | 0.9500 | C16—H16B | 0.9800 |
C5—C6 | 1.3894 (18) | C16—H16C | 0.9800 |
C5—H5 | 0.9500 | ||
O2—S1—O1 | 119.35 (5) | N2—C7—H7 | 119.7 |
O2—S1—N1 | 104.28 (5) | C8—C7—H7 | 119.7 |
O1—S1—N1 | 106.54 (5) | C9—C8—C7 | 124.46 (11) |
O2—S1—C1 | 110.04 (6) | C9—C8—C10 | 106.57 (11) |
O1—S1—C1 | 108.61 (5) | C7—C8—C10 | 128.97 (11) |
N1—S1—C1 | 107.30 (5) | N3—C9—C8 | 110.02 (11) |
N2—N1—S1 | 111.18 (7) | N3—C9—H9 | 125.0 |
N2—N1—H1N | 115.5 (12) | C8—C9—H9 | 125.0 |
S1—N1—H1N | 111.7 (12) | C11—C10—C15 | 118.99 (11) |
C7—N2—N1 | 113.81 (10) | C11—C10—C8 | 134.50 (11) |
C9—N3—C15 | 109.32 (10) | C15—C10—C8 | 106.50 (10) |
C9—N3—H3N | 126.3 (13) | C12—C11—C10 | 119.66 (11) |
C15—N3—H3N | 124.3 (13) | C12—C11—H11 | 120.2 |
C6—C1—C2 | 121.75 (12) | C10—C11—H11 | 120.2 |
C6—C1—S1 | 119.36 (9) | C11—C12—C13 | 119.59 (12) |
C2—C1—S1 | 118.87 (10) | C11—C12—C16 | 119.81 (12) |
C3—C2—C1 | 118.55 (13) | C13—C12—C16 | 120.56 (12) |
C3—C2—H2 | 120.7 | C14—C13—C12 | 122.11 (12) |
C1—C2—H2 | 120.7 | C14—C13—H13 | 118.9 |
C4—C3—C2 | 120.12 (13) | C12—C13—H13 | 118.9 |
C4—C3—H3 | 119.9 | C13—C14—C15 | 117.27 (12) |
C2—C3—H3 | 119.9 | C13—C14—H14 | 121.4 |
C3—C4—C5 | 120.80 (13) | C15—C14—H14 | 121.4 |
C3—C4—H4 | 119.6 | N3—C15—C14 | 130.13 (11) |
C5—C4—H4 | 119.6 | N3—C15—C10 | 107.58 (11) |
C4—C5—C6 | 120.02 (13) | C14—C15—C10 | 122.29 (11) |
C4—C5—H5 | 120.0 | C12—C16—H16A | 109.5 |
C6—C5—H5 | 120.0 | C12—C16—H16B | 109.5 |
C5—C6—C1 | 118.75 (12) | H16A—C16—H16B | 109.5 |
C5—C6—H6 | 120.6 | C12—C16—H16C | 109.5 |
C1—C6—H6 | 120.6 | H16A—C16—H16C | 109.5 |
N2—C7—C8 | 120.50 (11) | H16B—C16—H16C | 109.5 |
O2—S1—N1—N2 | −174.17 (7) | C7—C8—C9—N3 | 179.62 (11) |
O1—S1—N1—N2 | 58.73 (8) | C10—C8—C9—N3 | 0.16 (14) |
C1—S1—N1—N2 | −57.45 (8) | C9—C8—C10—C11 | 178.40 (13) |
S1—N1—N2—C7 | 175.77 (8) | C7—C8—C10—C11 | −1.0 (2) |
O2—S1—C1—C6 | −151.28 (9) | C9—C8—C10—C15 | −0.72 (13) |
O1—S1—C1—C6 | −18.95 (11) | C7—C8—C10—C15 | 179.85 (12) |
N1—S1—C1—C6 | 95.85 (10) | C15—C10—C11—C12 | −0.04 (17) |
O2—S1—C1—C2 | 29.91 (11) | C8—C10—C11—C12 | −179.07 (13) |
O1—S1—C1—C2 | 162.25 (10) | C10—C11—C12—C13 | −2.34 (18) |
N1—S1—C1—C2 | −82.95 (11) | C10—C11—C12—C16 | 175.45 (12) |
C6—C1—C2—C3 | 1.35 (19) | C11—C12—C13—C14 | 2.5 (2) |
S1—C1—C2—C3 | −179.87 (10) | C16—C12—C13—C14 | −175.25 (13) |
C1—C2—C3—C4 | −0.6 (2) | C12—C13—C14—C15 | −0.2 (2) |
C2—C3—C4—C5 | −0.4 (2) | C9—N3—C15—C14 | 178.29 (13) |
C3—C4—C5—C6 | 0.7 (2) | C9—N3—C15—C10 | −0.94 (14) |
C4—C5—C6—C1 | 0.01 (19) | C13—C14—C15—N3 | 178.60 (13) |
C2—C1—C6—C5 | −1.04 (18) | C13—C14—C15—C10 | −2.28 (18) |
S1—C1—C6—C5 | −179.81 (9) | C11—C10—C15—N3 | −178.27 (10) |
N1—N2—C7—C8 | 179.93 (10) | C8—C10—C15—N3 | 1.01 (13) |
N2—C7—C8—C9 | −173.47 (12) | C11—C10—C15—C14 | 2.43 (17) |
N2—C7—C8—C10 | 5.86 (19) | C8—C10—C15—C14 | −178.29 (11) |
C15—N3—C9—C8 | 0.48 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O1i | 0.87 (1) | 2.05 (1) | 2.924 (1) | 173 (2) |
N3—H3n···N1ii | 0.87 (1) | 2.16 (1) | 3.032 (1) | 177 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x+1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H15N3O2S |
Mr | 313.37 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 173 |
a, b, c (Å) | 13.3080 (2), 10.0043 (1), 23.7968 (3) |
V (Å3) | 3168.24 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.54 × 0.53 × 0.50 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41089, 3637, 3334 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.099, 1.01 |
No. of reflections | 3637 |
No. of parameters | 208 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.39 |
Computer programs: APEXII (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O1i | 0.87 (1) | 2.054 (9) | 2.924 (1) | 173.3 (16) |
N3—H3n···N1ii | 0.87 (1) | 2.163 (9) | 3.032 (1) | 176.7 (18) |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x+1/2, y, −z+1/2. |
The crystal structure of 2'-(1H-indol-3-ylmethylene)benzenesulfonohydrazine consists of molecules that are linked by Namino–H···Osulfonoy and Nindolyl–H···Nimino hydrogen bonds into layers (Ali, Yusnita, Wan Jefrey & Ng, 2007; Ali, Yusnita & Ng, 2007). The presence of the methyl substituent in the 5-position of the indolyl portion leads to a similar layer structure for the title compound (I).