Literature DB >> 21581392

(E)-N'-(5-Chloro-2-hydroxy-benzyl-idene)-p-toluene-sulfonohydrazide.

Reza Kia, Hoong-Kun Fun, Hadi Kargar.   

Abstract

The title compound, C(14)H(13)ClN(2)O(3)S, features an intra-molecular O-H⋯N hydrogen bond which generates an S(6) ring motif. Inter-molecular N-H⋯O hydrogen bonds and C-H⋯O close contacts link neighbouring mol-ecules forming R(2) (2)(13) ring motifs. In the crystal structure, mol-ecules are further linked by C-H⋯Cl inter-actions, forming one-dimensional extended chains along the c axis. The dihedral angle between the two benzene rings is 86.06 (3)°. The crystal structure is further stabilized by weak inter-molecular π-π inter-actions [inter-planar stacking distance = 3.357 (7) Å].

Entities:  

Year:  2008        PMID： 21581392      PMCID： PMC2960077          DOI： 10.1107/S1600536808038695

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures and applications, see, for example: Kayser et al. (2004 ▶); Tierney et al. (2006 ▶); Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Mehrabi et al. (2008 ▶); Kia et al. (2008 ▶). For the values of bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13ClN2O3S M = 324.78 Monoclinic, a = 15.7454 (3) Å b = 9.8338 (2) Å c = 9.8455 (2) Å β = 105.941 (1)° V = 1465.83 (5) Å3 Z = 4 Mo Kα radiation μ = 0.41 mm−1 T = 100.0 (1) K 0.45 × 0.38 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.836, T max = 0.883 16498 measured reflections 5274 independent reflections 4761 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.093 S = 1.10 5274 reflections 199 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.44 e Å−3 Δρmin = −0.38 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038695/pk2133sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038695/pk2133Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H13ClN2O3SF000 = 672
Mr = 324.78Dx = 1.472 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9969 reflections
a = 15.7454 (3) Åθ = 2.7–36.2º
b = 9.8338 (2) ŵ = 0.41 mm−1
c = 9.8455 (2) ÅT = 100.0 (1) K
β = 105.9410 (10)ºBlock, colourless
V = 1465.83 (5) Å30.45 × 0.38 × 0.31 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer5274 independent reflections
Radiation source: fine-focus sealed tube4761 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 100.0(1) Kθmax = 32.5º
φ and ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −16→23
Tmin = 0.836, Tmax = 0.883k = −11→14
16498 measured reflectionsl = −14→13
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093  w = 1/[σ2(Fo2) + (0.0458P)2 + 0.5147P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
5274 reflectionsΔρmax = 0.44 e Å−3
199 parametersΔρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Experimental. The low-temperature data was collected with the Oxford Cryosystems Cobra low-temperature attachment.
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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
Cl10.694874 (18)0.12795 (3)0.64129 (3)0.03146 (8)
S10.146818 (15)0.24140 (2)0.10615 (2)0.01365 (6)
O10.41411 (6)0.06452 (10)0.11049 (9)0.02515 (17)
O20.17263 (6)0.28771 (8)−0.01531 (8)0.02080 (15)
O30.07539 (5)0.30583 (8)0.14463 (8)0.01865 (14)
N10.31124 (5)0.20818 (9)0.23227 (9)0.01581 (15)
N20.23293 (5)0.26798 (9)0.24403 (9)0.01551 (15)
C10.47774 (7)0.08266 (11)0.23401 (11)0.02019 (19)
C20.56194 (8)0.03165 (13)0.24406 (13)0.0267 (2)
H2A0.5731−0.01210.16700.032*
C30.62907 (8)0.04587 (13)0.36843 (14)0.0277 (2)
H3A0.68500.01130.37510.033*
C40.61217 (7)0.11203 (12)0.48286 (13)0.0234 (2)
C50.52935 (7)0.16436 (11)0.47481 (12)0.02130 (19)
H5A0.51910.20880.55220.026*
C60.46098 (6)0.15033 (10)0.34992 (11)0.01791 (18)
C70.37483 (7)0.20586 (11)0.34673 (11)0.01807 (18)
H7A0.36550.24050.42940.022*
C80.13003 (6)0.06529 (10)0.09358 (10)0.01422 (16)
C90.16949 (7)−0.01247 (11)0.00975 (11)0.01837 (18)
H9A0.20110.0290−0.04600.022*
C100.16103 (7)−0.15310 (11)0.01051 (11)0.01982 (19)
H10A0.1873−0.2056−0.04530.024*
C110.11378 (6)−0.21695 (10)0.09355 (10)0.01714 (17)
C120.07307 (7)−0.13615 (11)0.17433 (11)0.01804 (18)
H12A0.0400−0.17730.22800.022*
C130.08123 (6)0.00428 (10)0.17580 (10)0.01632 (17)
H13A0.05450.05710.23080.020*
C140.10817 (8)−0.36948 (11)0.09768 (13)0.0235 (2)
H14A0.1204−0.40700.01500.035*
H14B0.0499−0.39580.10010.035*
H14C0.1506−0.40300.18050.035*
H1N20.2190 (11)0.2514 (16)0.3232 (17)0.028 (4)*
H1O10.3722 (14)0.093 (2)0.120 (2)0.050 (6)*
U11U22U33U12U13U23
Cl10.01936 (12)0.03239 (16)0.03641 (16)−0.00588 (10)−0.00283 (10)0.01246 (12)
S10.01639 (11)0.01291 (11)0.01269 (10)0.00087 (7)0.00572 (8)0.00034 (7)
O10.0244 (4)0.0326 (5)0.0194 (4)0.0074 (3)0.0076 (3)0.0000 (3)
O20.0311 (4)0.0184 (3)0.0158 (3)0.0000 (3)0.0114 (3)0.0026 (3)
O30.0183 (3)0.0169 (3)0.0220 (3)0.0041 (3)0.0076 (3)−0.0002 (3)
N10.0157 (3)0.0144 (4)0.0188 (4)0.0000 (3)0.0072 (3)−0.0004 (3)
N20.0154 (3)0.0173 (4)0.0151 (3)−0.0003 (3)0.0064 (3)−0.0029 (3)
C10.0208 (4)0.0195 (5)0.0215 (4)0.0030 (4)0.0079 (4)0.0043 (4)
C20.0249 (5)0.0272 (6)0.0307 (5)0.0076 (4)0.0123 (4)0.0047 (4)
C30.0197 (4)0.0264 (6)0.0384 (6)0.0053 (4)0.0101 (4)0.0096 (5)
C40.0170 (4)0.0210 (5)0.0300 (5)−0.0019 (4)0.0026 (4)0.0084 (4)
C50.0191 (4)0.0194 (5)0.0244 (5)−0.0022 (4)0.0042 (4)0.0019 (4)
C60.0170 (4)0.0156 (4)0.0214 (4)−0.0002 (3)0.0059 (3)0.0021 (3)
C70.0181 (4)0.0169 (4)0.0195 (4)−0.0008 (3)0.0057 (3)−0.0020 (3)
C80.0148 (4)0.0136 (4)0.0140 (4)0.0000 (3)0.0036 (3)−0.0005 (3)
C90.0231 (4)0.0164 (4)0.0182 (4)−0.0009 (3)0.0099 (3)−0.0018 (3)
C100.0238 (4)0.0165 (4)0.0207 (4)0.0007 (4)0.0087 (4)−0.0033 (3)
C110.0168 (4)0.0145 (4)0.0179 (4)−0.0004 (3)0.0009 (3)0.0000 (3)
C120.0169 (4)0.0177 (4)0.0201 (4)−0.0017 (3)0.0060 (3)0.0019 (3)
C130.0158 (4)0.0168 (4)0.0176 (4)0.0002 (3)0.0067 (3)−0.0004 (3)
C140.0267 (5)0.0151 (4)0.0265 (5)−0.0005 (4)0.0037 (4)0.0006 (4)
Cl1—C41.7429 (12)C5—H5A0.9300
S1—O31.4296 (7)C6—C71.4545 (14)
S1—O21.4386 (7)C7—H7A0.9300
S1—N21.6548 (9)C8—C91.3905 (13)
S1—C81.7512 (10)C8—C131.3954 (13)
O1—C11.3585 (14)C9—C101.3895 (15)
O1—H1O10.75 (2)C9—H9A0.9300
N1—C71.2858 (13)C10—C111.3965 (15)
N1—N21.3994 (11)C10—H10A0.9300
N2—H1N20.881 (17)C11—C121.3982 (15)
C1—C21.3954 (15)C11—C141.5037 (15)
C1—C61.4071 (15)C12—C131.3866 (14)
C2—C31.3875 (18)C12—H12A0.9300
C2—H2A0.9300C13—H13A0.9300
C3—C41.3886 (18)C14—H14A0.9600
C3—H3A0.9300C14—H14B0.9600
C4—C51.3838 (15)C14—H14C0.9600
C5—C61.4010 (14)
O3—S1—O2120.16 (5)C1—C6—C7122.79 (9)
O3—S1—N2103.86 (4)N1—C7—C6121.51 (9)
O2—S1—N2106.09 (5)N1—C7—H7A119.2
O3—S1—C8110.03 (5)C6—C7—H7A119.2
O2—S1—C8109.02 (5)C9—C8—C13120.99 (9)
N2—S1—C8106.73 (4)C9—C8—S1120.16 (7)
C1—O1—H1O1107.2 (16)C13—C8—S1118.73 (7)
C7—N1—N2115.26 (8)C10—C9—C8119.01 (9)
N1—N2—S1114.07 (6)C10—C9—H9A120.5
N1—N2—H1N2115.8 (11)C8—C9—H9A120.5
S1—N2—H1N2110.5 (11)C9—C10—C11121.19 (9)
O1—C1—C2117.97 (10)C9—C10—H10A119.4
O1—C1—C6122.12 (9)C11—C10—H10A119.4
C2—C1—C6119.91 (10)C10—C11—C12118.60 (9)
C3—C2—C1120.33 (11)C10—C11—C14120.60 (10)
C3—C2—H2A119.8C12—C11—C14120.79 (10)
C1—C2—H2A119.8C13—C12—C11121.08 (9)
C2—C3—C4119.61 (10)C13—C12—H12A119.5
C2—C3—H3A120.2C11—C12—H12A119.5
C4—C3—H3A120.2C12—C13—C8119.10 (9)
C5—C4—C3121.01 (11)C12—C13—H13A120.4
C5—C4—Cl1118.60 (10)C8—C13—H13A120.4
C3—C4—Cl1120.38 (9)C11—C14—H14A109.5
C4—C5—C6119.90 (11)C11—C14—H14B109.5
C4—C5—H5A120.0H14A—C14—H14B109.5
C6—C5—H5A120.0C11—C14—H14C109.5
C5—C6—C1119.23 (9)H14A—C14—H14C109.5
C5—C6—C7117.98 (9)H14B—C14—H14C109.5
C7—N1—N2—S1−167.94 (8)C5—C6—C7—N1173.45 (10)
O3—S1—N2—N1177.60 (7)C1—C6—C7—N1−7.19 (16)
O2—S1—N2—N1−54.83 (8)O3—S1—C8—C9155.84 (8)
C8—S1—N2—N161.33 (8)O2—S1—C8—C922.10 (10)
O1—C1—C2—C3−179.18 (11)N2—S1—C8—C9−92.09 (8)
C6—C1—C2—C30.77 (17)O3—S1—C8—C13−28.14 (9)
C1—C2—C3—C4−0.41 (18)O2—S1—C8—C13−161.88 (8)
C2—C3—C4—C5−0.12 (18)N2—S1—C8—C1383.93 (8)
C2—C3—C4—Cl1178.67 (9)C13—C8—C9—C10−1.10 (15)
C3—C4—C5—C60.28 (17)S1—C8—C9—C10174.83 (8)
Cl1—C4—C5—C6−178.53 (8)C8—C9—C10—C110.05 (16)
C4—C5—C6—C10.08 (16)C9—C10—C11—C121.41 (16)
C4—C5—C6—C7179.47 (10)C9—C10—C11—C14−177.60 (10)
O1—C1—C6—C5179.34 (10)C10—C11—C12—C13−1.86 (15)
C2—C1—C6—C5−0.60 (16)C14—C11—C12—C13177.14 (10)
O1—C1—C6—C7−0.01 (16)C11—C12—C13—C80.84 (15)
C2—C1—C6—C7−179.95 (10)C9—C8—C13—C120.66 (15)
N2—N1—C7—C6−178.29 (9)S1—C8—C13—C12−175.32 (8)
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.75 (2)2.00 (2)2.6690 (13)149 (2)
N2—H1N2···O2i0.881 (16)1.961 (17)2.8375 (12)172.8 (17)
C7—H7A···O1i0.932.593.3679 (14)142
C10—H10A···Cl1ii0.932.823.7256 (12)164
C12—H12A···O3iii0.932.483.3549 (14)157
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1O1⋯N10.75 (2)2.00 (2)2.6690 (13)149 (2)
N2—H1N2⋯O2i0.881 (16)1.961 (17)2.8375 (12)172.8 (17)
C7—H7A⋯O1i0.932.593.3679 (14)142
C10—H10A⋯Cl1ii0.932.823.7256 (12)164
C12—H12A⋯O3iii0.932.483.3549 (14)157

Symmetry codes: (i) ; (ii) ; (iii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  (E)-N'-(5-Bromo-2-hydroxy-benzyl-idene)-p-toluene-sulfonohydrazide.

Authors:  Reza Kia; Hoong-Kun Fun; Hadi Kargar
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-13

3.  (E)-N'-Benzyl-idene-p-toluene-sulfono-hydrazide.

Authors:  Hossein Mehrabi; Reza Kia; Ali Hassanzadeh; Samaneh Ghobadi; Hamid Reza Khavasi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-30
  3 in total
  3 in total

1.  (E)-N'-(4-Bromo-benzyl-idene)-p-toluene-sulfonohydrazide.

Authors:  Reza Kia; Bijan Etemadi; Hoong-Kun Fun; Hadi Kargar
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-25

2.  (E)-N'-(4-Chloro-benzyl-idene)-p-toluene-sulfonohydrazide 0.15-hydrate.

Authors:  Reza Kia; Hoong-Kun Fun; Hadi Kargar
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-25

3.  Crystal structure and Hirshfeld surface analysis of (E)-N'-benzyl-idene-4-chloro-benzene-sulfono-hydrazide and of its (E)-4-chloro-N'-(ortho- and para-methyl-benzyl-idene)benzene-sulfono-hydrazide derivatives.

Authors:  Akshatha R Salian; Sabine Foro; B Thimme Gowda
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-10-19
  3 in total

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