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The mol­ecules of of the title compound, C15H13N3O2S, are linked by Namino—H...Osulfon­yl and Nindol­yl—H...Nimino hydrogen bonds into a layer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009518/hb2309sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009518/hb2309Isup2.hkl
Contains datablock I

CCDC reference: 643005

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.074
  • Data-to-parameter ratio = 16.4

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
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3256 Count of symmetry unique reflns 1741 Completeness (_total/calc) 187.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1515 Fraction of Friedel pairs measured 0.870 Are heavy atom types Z>Si present yes
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 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

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.

2'-(1H-Indol-3-ylmethylene)benzenesulfonohydrazide top
Crystal data top
C15H13N3O2SF(000) = 624
Mr = 299.34Dx = 1.396 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 5770 reflections
a = 15.9617 (3) Åθ = 2.1–34.3°
b = 9.5265 (2) ŵ = 0.24 mm1
c = 9.3697 (2) ÅT = 173 K
V = 1424.75 (5) Å3Block, faint yellow
Z = 40.50 × 0.24 × 0.24 mm
Data collection top
Bruker APEXII
diffractometer
3256 independent reflections
Radiation source: medium-focus sealed tube3183 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1920
Tmin = 0.816, Tmax = 0.946k = 1212
12134 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0533P)2 + 0.1391P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3256 reflectionsΔρmax = 0.26 e Å3
198 parametersΔρmin = 0.24 e Å3
3 restraintsAbsolute structure: Flack (1983), 1517 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.794841 (15)0.59999 (3)0.50000 (3)0.01731 (9)
O10.82604 (6)0.66410 (11)0.37143 (10)0.0259 (2)
O20.71381 (5)0.53418 (10)0.49768 (13)0.02458 (19)
N11.03122 (7)1.02907 (13)0.96877 (12)0.0242 (3)
H1N1.0492 (11)1.0942 (15)1.0216 (18)0.028 (4)*
N20.86493 (6)0.77689 (11)0.66348 (12)0.0178 (2)
N30.78616 (6)0.72470 (12)0.62158 (12)0.0185 (2)
H3N0.7509 (11)0.7003 (19)0.6860 (18)0.034 (5)*
C10.87148 (7)0.48342 (12)0.56371 (14)0.0180 (2)
C20.85550 (9)0.41101 (14)0.68954 (16)0.0236 (3)
H20.80370.42220.73810.028*
C30.91692 (10)0.32175 (16)0.74303 (17)0.0314 (3)
H30.90670.27020.82800.038*
C40.99289 (9)0.30771 (16)0.6729 (2)0.0326 (3)
H41.03450.24640.71010.039*
C51.00858 (9)0.38243 (15)0.54905 (19)0.0315 (3)
H51.06120.37340.50240.038*
C60.94742 (8)0.47102 (13)0.49242 (17)0.0249 (3)
H60.95750.52180.40690.030*
C70.86688 (8)0.83770 (13)0.78553 (14)0.0189 (2)
H70.81710.84530.84050.023*
C80.94934 (8)0.99354 (14)0.94633 (15)0.0223 (3)
H80.90291.03140.99670.027*
C90.94426 (8)0.89463 (12)0.83970 (14)0.0188 (2)
C101.02890 (8)0.86306 (13)0.79651 (14)0.0181 (2)
C111.06579 (8)0.76598 (13)0.70294 (14)0.0213 (3)
H111.03210.70280.64940.026*
C121.15228 (9)0.76409 (15)0.69025 (17)0.0282 (3)
H121.17790.70010.62590.034*
C131.20261 (8)0.85529 (17)0.7711 (2)0.0337 (4)
H131.26170.85240.75940.040*
C141.16827 (9)0.94908 (16)0.86726 (18)0.0306 (3)
H141.20241.00980.92280.037*
C151.08119 (8)0.95049 (13)0.87898 (15)0.0221 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01470 (14)0.02269 (14)0.01454 (14)0.00186 (9)0.00156 (11)0.00021 (12)
O10.0262 (5)0.0349 (5)0.0167 (4)0.0013 (4)0.0003 (4)0.0040 (4)
O20.0163 (4)0.0296 (4)0.0278 (5)0.0046 (3)0.0061 (4)0.0027 (5)
N10.0235 (5)0.0236 (5)0.0256 (7)0.0026 (4)0.0019 (4)0.0092 (4)
N20.0155 (4)0.0178 (5)0.0202 (5)0.0023 (4)0.0018 (4)0.0021 (4)
N30.0147 (5)0.0218 (5)0.0190 (5)0.0014 (4)0.0012 (4)0.0014 (4)
C10.0147 (5)0.0203 (5)0.0191 (6)0.0004 (4)0.0025 (4)0.0033 (5)
C20.0209 (6)0.0274 (6)0.0224 (6)0.0006 (5)0.0018 (5)0.0004 (5)
C30.0340 (8)0.0298 (7)0.0304 (8)0.0014 (6)0.0107 (6)0.0039 (6)
C40.0275 (7)0.0263 (7)0.0440 (9)0.0060 (5)0.0148 (6)0.0098 (7)
C50.0189 (6)0.0302 (7)0.0454 (9)0.0022 (5)0.0012 (6)0.0157 (6)
C60.0208 (5)0.0271 (6)0.0270 (6)0.0024 (5)0.0038 (6)0.0070 (6)
C70.0183 (5)0.0183 (5)0.0202 (6)0.0011 (4)0.0018 (5)0.0004 (4)
C80.0220 (6)0.0223 (6)0.0226 (6)0.0006 (5)0.0001 (5)0.0031 (5)
C90.0196 (6)0.0182 (5)0.0185 (6)0.0010 (4)0.0004 (5)0.0002 (4)
C100.0196 (6)0.0167 (5)0.0182 (6)0.0002 (4)0.0009 (4)0.0019 (5)
C110.0253 (6)0.0181 (5)0.0206 (6)0.0021 (5)0.0011 (5)0.0008 (5)
C120.0259 (6)0.0262 (6)0.0324 (7)0.0070 (5)0.0023 (6)0.0027 (6)
C130.0198 (7)0.0352 (8)0.0460 (10)0.0022 (5)0.0006 (6)0.0042 (7)
C140.0218 (6)0.0297 (7)0.0403 (8)0.0031 (5)0.0023 (6)0.0070 (6)
C150.0230 (6)0.0199 (6)0.0234 (6)0.0012 (5)0.0015 (5)0.0022 (5)
Geometric parameters (Å, º) top
S1—O21.4375 (8)C5—C61.395 (2)
S1—O11.4395 (10)C5—H50.9500
S1—N31.6518 (11)C6—H60.9500
S1—C11.7567 (12)C7—C91.4413 (17)
N1—C81.3663 (17)C7—H70.9500
N1—C151.3800 (17)C8—C91.3757 (18)
N1—H1n0.84 (1)C8—H80.9500
N2—C71.2823 (17)C9—C101.4420 (17)
N2—N31.4079 (14)C10—C111.4038 (18)
N3—H3n0.86 (1)C10—C151.4097 (17)
C1—C61.3891 (17)C11—C121.3858 (19)
C1—C21.3895 (19)C11—H110.9500
C2—C31.391 (2)C12—C131.405 (2)
C2—H20.9500C12—H120.9500
C3—C41.386 (2)C13—C141.382 (2)
C3—H30.9500C13—H130.9500
C4—C51.384 (3)C14—C151.3944 (19)
C4—H40.9500C14—H140.9500
O2—S1—O1118.92 (6)C1—C6—H6120.7
O2—S1—N3104.40 (6)C5—C6—H6120.7
O1—S1—N3107.52 (6)N2—C7—C9120.32 (12)
O2—S1—C1110.85 (6)N2—C7—H7119.8
O1—S1—C1108.16 (6)C9—C7—H7119.8
N3—S1—C1106.19 (6)N1—C8—C9109.74 (12)
C8—N1—C15108.94 (11)N1—C8—H8125.1
C8—N1—H1N126.7 (12)C9—C8—H8125.1
C15—N1—H1N124.0 (13)C8—C9—C7124.33 (12)
C7—N2—N3115.46 (11)C8—C9—C10106.95 (12)
N2—N3—S1111.80 (8)C7—C9—C10128.72 (11)
N2—N3—H3N119.1 (14)C11—C10—C15118.90 (11)
S1—N3—H3N110.2 (13)C11—C10—C9134.88 (12)
C6—C1—C2121.73 (12)C15—C10—C9106.11 (11)
C6—C1—S1119.87 (10)C12—C11—C10118.68 (12)
C2—C1—S1118.32 (10)C12—C11—H11120.7
C1—C2—C3118.67 (13)C10—C11—H11120.7
C1—C2—H2120.7C11—C12—C13121.02 (13)
C3—C2—H2120.7C11—C12—H12119.5
C4—C3—C2120.33 (15)C13—C12—H12119.5
C4—C3—H3119.8C14—C13—C12121.63 (13)
C2—C3—H3119.8C14—C13—H13119.2
C5—C4—C3120.41 (13)C12—C13—H13119.2
C5—C4—H4119.8C13—C14—C15116.92 (13)
C3—C4—H4119.8C13—C14—H14121.5
C4—C5—C6120.21 (14)C15—C14—H14121.5
C4—C5—H5119.9N1—C15—C14129.00 (13)
C6—C5—H5119.9N1—C15—C10108.21 (11)
C1—C6—C5118.63 (15)C14—C15—C10122.77 (13)
C7—N2—N3—S1158.19 (9)N1—C8—C9—C102.10 (15)
O2—S1—N3—N2165.18 (8)N2—C7—C9—C8160.94 (13)
O1—S1—N3—N267.61 (10)N2—C7—C9—C1018.8 (2)
C1—S1—N3—N247.98 (10)C8—C9—C10—C11174.26 (14)
O2—S1—C1—C6134.06 (10)C7—C9—C10—C116.0 (2)
O1—S1—C1—C62.02 (12)C8—C9—C10—C151.82 (14)
N3—S1—C1—C6113.14 (11)C7—C9—C10—C15177.95 (13)
O2—S1—C1—C249.19 (12)C15—C10—C11—C122.9 (2)
O1—S1—C1—C2178.78 (10)C9—C10—C11—C12178.61 (14)
N3—S1—C1—C263.62 (11)C10—C11—C12—C131.2 (2)
C6—C1—C2—C31.37 (19)C11—C12—C13—C140.7 (3)
S1—C1—C2—C3178.06 (10)C12—C13—C14—C150.9 (2)
C1—C2—C3—C41.1 (2)C8—N1—C15—C14178.31 (15)
C2—C3—C4—C50.1 (2)C8—N1—C15—C100.37 (15)
C3—C4—C5—C61.0 (2)C13—C14—C15—N1177.58 (15)
C2—C1—C6—C50.47 (19)C13—C14—C15—C100.9 (2)
S1—C1—C6—C5177.11 (10)C11—C10—C15—N1175.93 (12)
C4—C5—C6—C10.7 (2)C9—C10—C15—N10.90 (15)
N3—N2—C7—C9179.72 (10)C11—C10—C15—C142.8 (2)
C15—N1—C8—C91.57 (15)C9—C10—C15—C14179.68 (14)
N1—C8—C9—C7177.68 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···N2i0.84 (1)2.27 (1)3.081 (2)161 (2)
N3—H3n···O1ii0.86 (1)2.16 (1)3.004 (2)170 (2)
Symmetry codes: (i) x+2, y+2, z+1/2; (ii) x+3/2, y, z+1/2.
 

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