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The mol­ecules of the title compound, C16H15N3O2S, are linked by an N—H(indol­yl)...O(sulfon­yl) hydrogen bond into a linear chain that runs along the a axis. A weak N—H(hydrazid­yl)...O(sulfon­yl) hydrogen bond links the chains into a layer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033740/hb2478sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033740/hb2478Isup2.hkl
Contains datablock I

CCDC reference: 657778

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.071
  • wR factor = 0.213
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.20 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H1<I>N< PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H3<I>N< PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.882(10) ...... 3.00 su-Ra N1 -H1N 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra N3 -H3N 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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 3 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

Comment top

Th structure of (1H-indole-3-methylene)benzenesulfonohydrazide consists of molecules that are hydrogen bonded into a layer motif; both the indolyl and amino groups are engaged in hydrogen bonding interactions (Ali et al., 2007). With the methyl-substituted title compound, the latter interaction is significantly weakened, so that the compound adopts only a chain structure. Adjacent molecules are linked into a chain that runs along the a axis of the unit cell.

Related literature top

For (1H-indole-3-methylene)benzenesulfonohydrazide, see Ali et al. (2007).

Experimental top

Benzenesulfohydrazine (0.30 g, 1.7 mmol) and 2-methylindole-3-carboxaldehyde (0.28 g, 1.7 mmol) were dissolved in ethanol (50 ml). The reactants were heated under reflux for 1 h. Slow evaporation of the solvent gve the Schiff base.

Refinement top

The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and they were included in the refinement in the riding model approximation with U(H) set to 1.2Ueq(C). The amino H atoms were located in a difference Fourier map, and were refined with a distance restraint (N–H 0.88 Å); their temperature factors were freely refined.

Structure description top

Th structure of (1H-indole-3-methylene)benzenesulfonohydrazide consists of molecules that are hydrogen bonded into a layer motif; both the indolyl and amino groups are engaged in hydrogen bonding interactions (Ali et al., 2007). With the methyl-substituted title compound, the latter interaction is significantly weakened, so that the compound adopts only a chain structure. Adjacent molecules are linked into a chain that runs along the a axis of the unit cell.

For (1H-indole-3-methylene)benzenesulfonohydrazide, see Ali et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of C16H15N3O2S. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii. The dashed lines denote hydrogen bonds.
2'-(2-Methyl-1H-indol-3-ylmethylene)benzenesulfonohydrazide top
Crystal data top
C16H15N3O2SF(000) = 656
Mr = 313.37Dx = 1.437 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8732 reflections
a = 11.1512 (11) Åθ = 2.8–30.6°
b = 19.243 (2) ŵ = 0.24 mm1
c = 6.9905 (8) ÅT = 173 K
β = 105.076 (6)°Block, yellow
V = 1448.4 (3) Å30.45 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
1919 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.087
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
φ and ω scansh = 1313
8053 measured reflectionsk = 2223
2829 independent reflectionsl = 68
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0886P)2]
where P = (Fo2 + 2Fc2)/3
2829 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.51 e Å3
2 restraintsΔρmin = 0.63 e Å3
Crystal data top
C16H15N3O2SV = 1448.4 (3) Å3
Mr = 313.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.1512 (11) ŵ = 0.24 mm1
b = 19.243 (2) ÅT = 173 K
c = 6.9905 (8) Å0.45 × 0.20 × 0.20 mm
β = 105.076 (6)°
Data collection top
Bruker APEXII
diffractometer
1919 reflections with I > 2σ(I)
8053 measured reflectionsRint = 0.087
2829 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0712 restraints
wR(F2) = 0.213H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.51 e Å3
2829 reflectionsΔρmin = 0.63 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.98807 (9)0.33779 (5)0.84350 (13)0.0201 (3)
O11.1071 (3)0.32097 (13)0.9723 (4)0.0256 (7)
O20.9785 (3)0.35803 (14)0.6438 (4)0.0246 (7)
N10.3755 (3)0.19967 (16)0.5410 (4)0.0211 (7)
H1N0.309 (2)0.1732 (16)0.512 (5)0.015 (10)*
N20.7768 (3)0.28039 (16)0.7403 (4)0.0208 (7)
N30.9041 (3)0.26672 (16)0.8314 (5)0.0208 (7)
H3N0.922 (5)0.245 (2)0.946 (4)0.048 (15)*
C10.3744 (4)0.27162 (19)0.5421 (5)0.0200 (8)
C20.2749 (4)0.3174 (2)0.4925 (5)0.0242 (9)
H20.19190.30130.44610.029*
C30.3024 (4)0.3875 (2)0.5139 (5)0.0251 (9)
H30.23660.42030.48200.030*
C40.4239 (4)0.41119 (19)0.5809 (5)0.0243 (9)
H40.43930.45980.59350.029*
C50.5229 (4)0.3655 (2)0.6297 (5)0.0224 (9)
H50.60560.38220.67600.027*
C60.4987 (4)0.29412 (19)0.6094 (5)0.0181 (8)
C70.5742 (4)0.23212 (19)0.6511 (5)0.0180 (8)
C80.4946 (4)0.17566 (19)0.6077 (5)0.0191 (8)
C90.5214 (4)0.09976 (19)0.6243 (5)0.0245 (9)
H9A0.48190.07700.49820.037*
H9B0.48860.08000.72960.037*
H9C0.61140.09230.65600.037*
C100.7056 (4)0.22701 (18)0.7316 (5)0.0191 (8)
H100.74120.18350.77960.023*
C110.9191 (4)0.40312 (18)0.9554 (5)0.0201 (8)
C120.8402 (4)0.45112 (19)0.8375 (5)0.0218 (9)
H120.82260.44850.69730.026*
C130.7874 (4)0.5029 (2)0.9274 (6)0.0269 (9)
H130.73470.53660.84850.032*
C140.8115 (4)0.5055 (2)1.1316 (6)0.0260 (9)
H140.77480.54091.19250.031*
C150.8889 (4)0.4566 (2)1.2477 (5)0.0255 (9)
H150.90460.45851.38790.031*
C160.9433 (4)0.4051 (2)1.1601 (5)0.0239 (9)
H160.99650.37161.23930.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0182 (6)0.0181 (5)0.0225 (5)0.0006 (4)0.0025 (4)0.0002 (3)
O10.0181 (16)0.0220 (14)0.0315 (15)0.0037 (11)0.0026 (11)0.0006 (11)
O20.0247 (17)0.0251 (15)0.0251 (15)0.0011 (12)0.0082 (12)0.0005 (11)
N10.0191 (19)0.0176 (17)0.0244 (17)0.0020 (14)0.0014 (13)0.0016 (12)
N20.0173 (18)0.0208 (17)0.0214 (16)0.0006 (13)0.0000 (13)0.0017 (12)
N30.0177 (19)0.0160 (16)0.0253 (18)0.0002 (13)0.0003 (14)0.0013 (13)
C10.023 (2)0.0186 (19)0.0170 (18)0.0024 (16)0.0030 (15)0.0018 (14)
C20.022 (2)0.026 (2)0.024 (2)0.0005 (17)0.0039 (16)0.0009 (15)
C30.030 (3)0.022 (2)0.021 (2)0.0070 (17)0.0038 (16)0.0026 (15)
C40.034 (3)0.0165 (19)0.022 (2)0.0002 (17)0.0076 (17)0.0017 (15)
C50.028 (2)0.0205 (19)0.0177 (19)0.0041 (17)0.0037 (15)0.0020 (14)
C60.021 (2)0.021 (2)0.0113 (17)0.0015 (16)0.0031 (14)0.0006 (14)
C70.019 (2)0.0214 (19)0.0132 (17)0.0006 (16)0.0036 (14)0.0011 (13)
C80.024 (2)0.0185 (18)0.0150 (17)0.0004 (16)0.0050 (15)0.0012 (14)
C90.028 (2)0.018 (2)0.026 (2)0.0009 (17)0.0040 (16)0.0001 (15)
C100.024 (2)0.0175 (19)0.0154 (18)0.0009 (15)0.0037 (15)0.0006 (14)
C110.020 (2)0.0163 (19)0.025 (2)0.0025 (15)0.0075 (15)0.0007 (14)
C120.023 (2)0.020 (2)0.021 (2)0.0007 (16)0.0043 (16)0.0042 (14)
C130.026 (2)0.022 (2)0.033 (2)0.0033 (17)0.0080 (17)0.0038 (16)
C140.030 (2)0.019 (2)0.032 (2)0.0022 (17)0.0128 (17)0.0038 (16)
C150.035 (3)0.024 (2)0.0182 (19)0.0049 (18)0.0079 (17)0.0021 (15)
C160.022 (2)0.022 (2)0.027 (2)0.0028 (16)0.0048 (16)0.0020 (15)
Geometric parameters (Å, º) top
S1—O21.426 (3)C6—C71.445 (5)
S1—O11.433 (3)C7—C81.386 (5)
S1—N31.647 (3)C7—C101.430 (5)
S1—C111.759 (4)C8—C91.489 (5)
N1—C81.368 (5)C9—H9A0.9800
N1—C11.385 (5)C9—H9B0.9800
N1—H1N0.882 (10)C9—H9C0.9800
N2—C101.290 (5)C10—H100.9500
N2—N31.422 (4)C11—C161.386 (5)
N3—H3N0.880 (10)C11—C121.389 (5)
C1—C21.388 (5)C12—C131.388 (5)
C1—C61.411 (5)C12—H120.9500
C2—C31.383 (5)C13—C141.383 (5)
C2—H20.9500C13—H130.9500
C3—C41.390 (6)C14—C151.387 (6)
C3—H30.9500C14—H140.9500
C4—C51.382 (6)C15—C161.385 (5)
C4—H40.9500C15—H150.9500
C5—C61.401 (5)C16—H160.9500
C5—H50.9500
O2—S1—O1119.85 (18)C8—C7—C6107.3 (3)
O2—S1—N3106.27 (16)C10—C7—C6128.3 (3)
O1—S1—N3105.40 (16)N1—C8—C7108.6 (3)
O2—S1—C11108.05 (17)N1—C8—C9121.0 (3)
O1—S1—C11108.79 (17)C7—C8—C9130.4 (4)
N3—S1—C11107.93 (18)C8—C9—H9A109.5
C8—N1—C1110.2 (3)C8—C9—H9B109.5
C8—N1—H1N125 (3)H9A—C9—H9B109.5
C1—N1—H1N125 (3)C8—C9—H9C109.5
C10—N2—N3113.8 (3)H9A—C9—H9C109.5
N2—N3—S1110.9 (2)H9B—C9—H9C109.5
N2—N3—H3N117 (4)N2—C10—C7121.2 (3)
S1—N3—H3N111 (3)N2—C10—H10119.4
N1—C1—C2129.8 (4)C7—C10—H10119.4
N1—C1—C6107.4 (3)C16—C11—C12121.2 (4)
C2—C1—C6122.7 (3)C16—C11—S1119.2 (3)
C3—C2—C1116.8 (4)C12—C11—S1119.6 (3)
C3—C2—H2121.6C13—C12—C11119.1 (3)
C1—C2—H2121.6C13—C12—H12120.4
C2—C3—C4121.7 (4)C11—C12—H12120.4
C2—C3—H3119.1C14—C13—C12120.1 (4)
C4—C3—H3119.1C14—C13—H13119.9
C5—C4—C3121.3 (4)C12—C13—H13119.9
C5—C4—H4119.3C13—C14—C15120.2 (4)
C3—C4—H4119.3C13—C14—H14119.9
C4—C5—C6118.6 (4)C15—C14—H14119.9
C4—C5—H5120.7C16—C15—C14120.3 (3)
C6—C5—H5120.7C16—C15—H15119.9
C5—C6—C1118.8 (4)C14—C15—H15119.9
C5—C6—C7134.7 (4)C15—C16—C11119.1 (4)
C1—C6—C7106.5 (3)C15—C16—H16120.5
C8—C7—C10124.4 (3)C11—C16—H16120.5
C10—N2—N3—S1178.1 (3)C1—N1—C8—C9179.0 (3)
O2—S1—N3—N263.5 (3)C10—C7—C8—N1177.6 (3)
O1—S1—N3—N2168.4 (2)C6—C7—C8—N10.4 (4)
C11—S1—N3—N252.2 (3)C10—C7—C8—C92.3 (6)
C8—N1—C1—C2177.9 (4)C6—C7—C8—C9179.5 (3)
C8—N1—C1—C61.0 (4)N3—N2—C10—C7177.7 (3)
N1—C1—C2—C3178.1 (3)C8—C7—C10—N2169.2 (3)
C6—C1—C2—C30.7 (5)C6—C7—C10—N214.2 (6)
C1—C2—C3—C40.3 (5)O2—S1—C11—C16163.7 (3)
C2—C3—C4—C50.1 (6)O1—S1—C11—C1632.1 (4)
C3—C4—C5—C60.3 (5)N3—S1—C11—C1681.7 (3)
C4—C5—C6—C10.7 (5)O2—S1—C11—C1217.2 (4)
C4—C5—C6—C7177.1 (4)O1—S1—C11—C12148.8 (3)
N1—C1—C6—C5178.2 (3)N3—S1—C11—C1297.3 (3)
C2—C1—C6—C50.9 (5)C16—C11—C12—C131.6 (6)
N1—C1—C6—C70.8 (4)S1—C11—C12—C13179.3 (3)
C2—C1—C6—C7178.3 (3)C11—C12—C13—C141.3 (6)
C5—C6—C7—C8177.0 (4)C12—C13—C14—C150.3 (6)
C1—C6—C7—C80.3 (4)C13—C14—C15—C160.4 (6)
C5—C6—C7—C100.0 (7)C14—C15—C16—C110.1 (6)
C1—C6—C7—C10176.8 (3)C12—C11—C16—C150.9 (6)
C1—N1—C8—C70.9 (4)S1—C11—C16—C15180.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.88 (1)2.20 (3)2.933 (4)141 (3)
N3—H3n···O2ii0.88 (1)2.40 (2)3.206 (4)152 (4)
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H15N3O2S
Mr313.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)11.1512 (11), 19.243 (2), 6.9905 (8)
β (°) 105.076 (6)
V3)1448.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.45 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8053, 2829, 1919
Rint0.087
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.213, 1.15
No. of reflections2829
No. of parameters208
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.51, 0.63

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.88 (1)2.20 (3)2.933 (4)141 (3)
N3—H3n···O2ii0.88 (1)2.40 (2)3.206 (4)152 (4)
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
 

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