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The mol­ecules of the title compound, C16H15N3O2S, are linked by Namino–H...Osulfon­yl and Nindol­yl–H...Nimino hydrogen bonds into a layer motif. The dihedral angle between the aromatic ring mean planes in the mol­ecule is 78.85 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020065/hb2390sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020065/hb2390Isup2.hkl
Contains datablock I

CCDC reference: 647713

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.099
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. Faint PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The crystal structure of 2'-(1H-indol-3-ylmethylene)benzenesulfonohydrazine consists of molecules that are linked by NaminoH···Osulfonoy and NindolylH···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).

Related literature top

For related structures, see: Ali, Yusnita et al. (2007); Ali, Yusnita & Ng (2007).

Experimental top

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).

Refinement top

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.

Structure description top

The crystal structure of 2'-(1H-indol-3-ylmethylene)benzenesulfonohydrazine consists of molecules that are linked by NaminoH···Osulfonoy and NindolylH···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).

Computing details top

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.

Figures top
[Figure 1] 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.
2'-(5-Methyl-1H-indol-3-ylmethylene)benzenesulfonohydrazine top
Crystal data top
C16H15N3O2SF(000) = 1312
Mr = 313.37Dx = 1.314 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9953 reflections
a = 13.3080 (2) Åθ = 2.3–33.9°
b = 10.0043 (1) ŵ = 0.21 mm1
c = 23.7968 (3) ÅT = 173 K
V = 3168.24 (7) Å3Irregular block, faint yellow
Z = 80.54 × 0.53 × 0.50 mm
Data collection top
Bruker APEXII CCD
diffractometer
3334 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
φ and ω scansh = 1717
41089 measured reflectionsk = 1212
3637 independent reflectionsl = 3030
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)] = 0.031Hydrogen site location: difmap and geom
wR(F2) = 0.099H 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 parametersΔρmax = 0.34 e Å3
2 restraintsΔρmin = 0.39 e Å3
Crystal data top
C16H15N3O2SV = 3168.24 (7) Å3
Mr = 313.37Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.3080 (2) ŵ = 0.21 mm1
b = 10.0043 (1) ÅT = 173 K
c = 23.7968 (3) Å0.54 × 0.53 × 0.50 mm
Data collection top
Bruker APEXII CCD
diffractometer
3334 reflections with I > 2σ(I)
41089 measured reflectionsRint = 0.025
3637 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0312 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.34 e Å3
3637 reflectionsΔρmin = 0.39 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.23027 (2)0.11903 (3)0.421914 (12)0.01747 (10)
O10.21446 (7)0.25306 (8)0.40210 (4)0.0244 (2)
O20.14557 (6)0.04044 (9)0.43913 (4)0.0248 (2)
N10.27929 (7)0.03416 (10)0.36867 (4)0.0181 (2)
H1N0.2819 (13)0.0515 (10)0.3758 (7)0.035 (5)*
N20.37106 (7)0.09299 (10)0.35018 (4)0.0191 (2)
N30.64312 (8)0.08303 (12)0.23137 (4)0.0247 (2)
H3N0.6840 (12)0.0675 (19)0.2036 (6)0.046 (5)*
C10.32075 (9)0.12280 (11)0.47563 (5)0.0190 (2)
C20.32850 (10)0.01370 (13)0.51174 (5)0.0265 (3)
H20.28580.06170.50740.032*
C30.40021 (12)0.01753 (15)0.55427 (6)0.0342 (3)
H30.40630.05540.57960.041*
C40.46263 (12)0.12737 (15)0.55972 (6)0.0346 (3)
H40.51110.12940.58900.041*
C50.45525 (10)0.23442 (14)0.52298 (6)0.0299 (3)
H50.49900.30880.52690.036*
C60.38383 (9)0.23295 (12)0.48040 (5)0.0230 (2)
H60.37820.30590.45500.028*
C70.41556 (9)0.02655 (12)0.31144 (5)0.0211 (2)
H70.38660.05400.29790.025*
C80.50919 (9)0.07311 (12)0.28826 (5)0.0207 (2)
C90.55733 (10)0.01550 (13)0.24299 (5)0.0251 (3)
H90.53380.06040.22290.030*
C100.57019 (9)0.18475 (11)0.30554 (5)0.0190 (2)
C110.56175 (9)0.28304 (12)0.34724 (5)0.0210 (2)
H110.50580.28310.37200.025*
C120.63569 (10)0.38036 (13)0.35217 (5)0.0251 (3)
C130.72032 (10)0.37621 (13)0.31648 (6)0.0277 (3)
H130.77180.44110.32120.033*
C140.73080 (9)0.28053 (13)0.27478 (6)0.0258 (3)
H140.78800.27890.25090.031*
C150.65415 (9)0.18704 (12)0.26929 (5)0.0211 (2)
C160.62308 (12)0.49234 (16)0.39414 (7)0.0379 (3)
H16A0.55750.53490.38860.057*
H16B0.67640.55860.38870.057*
H16C0.62710.45620.43230.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01618 (16)0.01306 (16)0.02316 (17)0.00111 (9)0.00103 (10)0.00258 (10)
O10.0252 (4)0.0141 (4)0.0339 (5)0.0034 (3)0.0041 (4)0.0049 (3)
O20.0187 (4)0.0206 (4)0.0350 (5)0.0012 (3)0.0028 (3)0.0033 (4)
N10.0188 (5)0.0137 (4)0.0218 (5)0.0015 (3)0.0007 (4)0.0017 (4)
N20.0189 (5)0.0178 (5)0.0207 (5)0.0026 (4)0.0012 (4)0.0031 (4)
N30.0255 (5)0.0275 (5)0.0213 (5)0.0030 (4)0.0038 (4)0.0028 (4)
C10.0199 (5)0.0182 (5)0.0189 (5)0.0033 (4)0.0002 (4)0.0006 (4)
C20.0303 (7)0.0240 (6)0.0253 (6)0.0022 (5)0.0004 (5)0.0045 (5)
C30.0405 (8)0.0373 (8)0.0247 (6)0.0098 (6)0.0038 (6)0.0072 (5)
C40.0333 (7)0.0449 (9)0.0254 (6)0.0097 (6)0.0091 (6)0.0064 (6)
C50.0256 (6)0.0302 (7)0.0340 (7)0.0026 (5)0.0043 (5)0.0106 (5)
C60.0230 (6)0.0188 (5)0.0271 (6)0.0027 (4)0.0007 (5)0.0031 (4)
C70.0216 (5)0.0191 (5)0.0226 (5)0.0009 (4)0.0035 (4)0.0008 (4)
C80.0219 (6)0.0202 (6)0.0200 (5)0.0014 (5)0.0014 (4)0.0010 (4)
C90.0262 (6)0.0241 (6)0.0251 (6)0.0012 (5)0.0009 (5)0.0046 (5)
C100.0204 (5)0.0182 (5)0.0183 (5)0.0024 (4)0.0007 (4)0.0030 (4)
C110.0229 (6)0.0215 (6)0.0187 (5)0.0021 (5)0.0002 (4)0.0004 (4)
C120.0273 (6)0.0227 (6)0.0252 (6)0.0001 (5)0.0028 (5)0.0021 (5)
C130.0263 (6)0.0245 (6)0.0325 (7)0.0053 (5)0.0011 (5)0.0018 (5)
C140.0234 (6)0.0271 (6)0.0269 (6)0.0002 (5)0.0035 (5)0.0041 (5)
C150.0230 (6)0.0210 (6)0.0193 (5)0.0038 (5)0.0005 (4)0.0024 (4)
C160.0369 (8)0.0349 (8)0.0418 (8)0.0054 (6)0.0011 (6)0.0160 (6)
Geometric parameters (Å, º) top
S1—O21.4340 (9)C6—H60.9500
S1—O11.4369 (9)C7—C81.4401 (17)
S1—N11.6589 (10)C7—H70.9500
S1—C11.7566 (12)C8—C91.3794 (17)
N1—N21.4253 (13)C8—C101.4406 (17)
N1—H1N0.874 (9)C9—H90.9500
N2—C71.2816 (16)C10—C111.4015 (16)
N3—C91.3551 (17)C10—C151.4119 (16)
N3—C151.3851 (16)C11—C121.3892 (18)
N3—H3N0.870 (9)C11—H110.9500
C1—C61.3899 (17)C12—C131.4112 (19)
C1—C21.3929 (17)C12—C161.5101 (18)
C2—C31.3914 (19)C13—C141.3858 (19)
C2—H20.9500C13—H130.9500
C3—C41.384 (2)C14—C151.3901 (18)
C3—H30.9500C14—H140.9500
C4—C51.386 (2)C16—H16A0.9800
C4—H40.9500C16—H16B0.9800
C5—C61.3894 (18)C16—H16C0.9800
C5—H50.9500
O2—S1—O1119.35 (5)N2—C7—H7119.7
O2—S1—N1104.28 (5)C8—C7—H7119.7
O1—S1—N1106.54 (5)C9—C8—C7124.46 (11)
O2—S1—C1110.04 (6)C9—C8—C10106.57 (11)
O1—S1—C1108.61 (5)C7—C8—C10128.97 (11)
N1—S1—C1107.30 (5)N3—C9—C8110.02 (11)
N2—N1—S1111.18 (7)N3—C9—H9125.0
N2—N1—H1N115.5 (12)C8—C9—H9125.0
S1—N1—H1N111.7 (12)C11—C10—C15118.99 (11)
C7—N2—N1113.81 (10)C11—C10—C8134.50 (11)
C9—N3—C15109.32 (10)C15—C10—C8106.50 (10)
C9—N3—H3N126.3 (13)C12—C11—C10119.66 (11)
C15—N3—H3N124.3 (13)C12—C11—H11120.2
C6—C1—C2121.75 (12)C10—C11—H11120.2
C6—C1—S1119.36 (9)C11—C12—C13119.59 (12)
C2—C1—S1118.87 (10)C11—C12—C16119.81 (12)
C3—C2—C1118.55 (13)C13—C12—C16120.56 (12)
C3—C2—H2120.7C14—C13—C12122.11 (12)
C1—C2—H2120.7C14—C13—H13118.9
C4—C3—C2120.12 (13)C12—C13—H13118.9
C4—C3—H3119.9C13—C14—C15117.27 (12)
C2—C3—H3119.9C13—C14—H14121.4
C3—C4—C5120.80 (13)C15—C14—H14121.4
C3—C4—H4119.6N3—C15—C14130.13 (11)
C5—C4—H4119.6N3—C15—C10107.58 (11)
C4—C5—C6120.02 (13)C14—C15—C10122.29 (11)
C4—C5—H5120.0C12—C16—H16A109.5
C6—C5—H5120.0C12—C16—H16B109.5
C5—C6—C1118.75 (12)H16A—C16—H16B109.5
C5—C6—H6120.6C12—C16—H16C109.5
C1—C6—H6120.6H16A—C16—H16C109.5
N2—C7—C8120.50 (11)H16B—C16—H16C109.5
O2—S1—N1—N2174.17 (7)C7—C8—C9—N3179.62 (11)
O1—S1—N1—N258.73 (8)C10—C8—C9—N30.16 (14)
C1—S1—N1—N257.45 (8)C9—C8—C10—C11178.40 (13)
S1—N1—N2—C7175.77 (8)C7—C8—C10—C111.0 (2)
O2—S1—C1—C6151.28 (9)C9—C8—C10—C150.72 (13)
O1—S1—C1—C618.95 (11)C7—C8—C10—C15179.85 (12)
N1—S1—C1—C695.85 (10)C15—C10—C11—C120.04 (17)
O2—S1—C1—C229.91 (11)C8—C10—C11—C12179.07 (13)
O1—S1—C1—C2162.25 (10)C10—C11—C12—C132.34 (18)
N1—S1—C1—C282.95 (11)C10—C11—C12—C16175.45 (12)
C6—C1—C2—C31.35 (19)C11—C12—C13—C142.5 (2)
S1—C1—C2—C3179.87 (10)C16—C12—C13—C14175.25 (13)
C1—C2—C3—C40.6 (2)C12—C13—C14—C150.2 (2)
C2—C3—C4—C50.4 (2)C9—N3—C15—C14178.29 (13)
C3—C4—C5—C60.7 (2)C9—N3—C15—C100.94 (14)
C4—C5—C6—C10.01 (19)C13—C14—C15—N3178.60 (13)
C2—C1—C6—C51.04 (18)C13—C14—C15—C102.28 (18)
S1—C1—C6—C5179.81 (9)C11—C10—C15—N3178.27 (10)
N1—N2—C7—C8179.93 (10)C8—C10—C15—N31.01 (13)
N2—C7—C8—C9173.47 (12)C11—C10—C15—C142.43 (17)
N2—C7—C8—C105.86 (19)C8—C10—C15—C14178.29 (11)
C15—N3—C9—C80.48 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.87 (1)2.05 (1)2.924 (1)173 (2)
N3—H3n···N1ii0.87 (1)2.16 (1)3.032 (1)177 (2)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H15N3O2S
Mr313.37
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)173
a, b, c (Å)13.3080 (2), 10.0043 (1), 23.7968 (3)
V3)3168.24 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.54 × 0.53 × 0.50
Data collection
DiffractometerBruker APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
41089, 3637, 3334
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.099, 1.01
No. of reflections3637
No. of parameters208
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.39

Computer programs: APEXII (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.87 (1)2.054 (9)2.924 (1)173.3 (16)
N3—H3n···N1ii0.87 (1)2.163 (9)3.032 (1)176.7 (18)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y, z+1/2.
 

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