organic compounds
1-(6-Chloro-1,3-benzothiazol-2-yl)-2-[1-(4-methoxyphenyl)ethylidene]hydrazine
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, and cDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India
*Correspondence e-mail: hkfun@usm.my
The 16H14ClN3OS, contains two independent molecules (A and B) linked into dimers via N—H⋯N hydrogen bonds. The 1,3-benzothiazol-2-yl ring system and the benzene ring form dihedral angles of 17.08 (8) and 8.63 (7)° in molecules A and B, respectively.
of the title compound, CRelated literature
For general background to and the biological, physical and chemical activities of hydrazone derivatives, see: Rollas & Küçükgüzel (2007); Naseema et al. (2010); Fouda et al. (2007); Dutkiewicz et al. (2010); Ali et al. (2004); Zeb & Yousuf (2011). For related structures, see: Fun et al. (2012a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; 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, 2009).
Supporting information
10.1107/S1600536812032606/cv5320sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812032606/cv5320Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812032606/cv5320Isup3.cml
A mixture of 1-(6-chloro1,3-benzothiazol-2-yl)hydrazine (1.99 g, 10 mmol) and 4-methoxyacetophenone (1.5 g, 10 mmol) in ethanol (50 ml) was refluxed for 4 h. Completion of the reaction was monitored by TLC. After completion of the reaction, the reaction-mixture was poured into ice water. Brown colored solid separated out. The product obtained was washed with water and dried. The crude product was recrystallized from ethanol. Single crystals were grown by slow evaporation from solvent ethanol (m.p. 451–453 K).
N-bound H atoms were located in a difference Fourier map and isotropically refined with a restraint N—H = 0.85 (3) Å. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 or 0.98 Å and Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl groups.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The content of asymmetric unit of (I) showing 50% probability displacement ellipsoids for non-H atoms. Intermolecular hydrogen bonds are shown as dashed lines. |
C16H14ClN3OS | Z = 4 |
Mr = 331.81 | F(000) = 688 |
Triclinic, P1 | Dx = 1.456 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5294 (1) Å | Cell parameters from 9939 reflections |
b = 9.3097 (1) Å | θ = 2.2–32.9° |
c = 19.8115 (3) Å | µ = 0.40 mm−1 |
α = 87.999 (1)° | T = 100 K |
β = 78.091 (1)° | Plate, brown |
γ = 79.461 (1)° | 0.25 × 0.20 × 0.06 mm |
V = 1513.32 (3) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 6907 independent reflections |
Radiation source: fine-focus sealed tube | 5393 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→11 |
Tmin = 0.908, Tmax = 0.976 | k = −12→12 |
31608 measured reflections | l = −25→25 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.028P)2 + 1.121P] where P = (Fo2 + 2Fc2)/3 |
6907 reflections | (Δ/σ)max = 0.001 |
409 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C16H14ClN3OS | γ = 79.461 (1)° |
Mr = 331.81 | V = 1513.32 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.5294 (1) Å | Mo Kα radiation |
b = 9.3097 (1) Å | µ = 0.40 mm−1 |
c = 19.8115 (3) Å | T = 100 K |
α = 87.999 (1)° | 0.25 × 0.20 × 0.06 mm |
β = 78.091 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 6907 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5393 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.976 | Rint = 0.044 |
31608 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.36 e Å−3 |
6907 reflections | Δρmin = −0.40 e Å−3 |
409 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.35667 (6) | 0.80375 (5) | 0.42848 (3) | 0.01905 (12) | |
Cl1A | 0.92646 (7) | 1.02723 (6) | 0.36901 (3) | 0.02725 (13) | |
O1A | −0.47274 (18) | 0.77478 (16) | 0.68927 (7) | 0.0251 (3) | |
N1A | 0.4366 (2) | 0.71715 (17) | 0.29901 (8) | 0.0170 (4) | |
N2A | 0.1864 (2) | 0.66677 (19) | 0.36002 (9) | 0.0179 (4) | |
N3A | 0.0764 (2) | 0.69008 (17) | 0.42147 (8) | 0.0176 (4) | |
C1A | 0.5390 (2) | 0.8395 (2) | 0.37855 (10) | 0.0173 (4) | |
C2A | 0.6504 (3) | 0.9150 (2) | 0.39716 (11) | 0.0200 (4) | |
H2AA | 0.6336 | 0.9545 | 0.4422 | 0.024* | |
C3A | 0.7863 (3) | 0.9303 (2) | 0.34768 (11) | 0.0202 (4) | |
C4A | 0.8153 (3) | 0.8714 (2) | 0.28172 (11) | 0.0204 (4) | |
H4AA | 0.9115 | 0.8819 | 0.2493 | 0.025* | |
C5A | 0.7029 (2) | 0.7971 (2) | 0.26351 (11) | 0.0195 (4) | |
H5AA | 0.7218 | 0.7564 | 0.2186 | 0.023* | |
C6A | 0.5629 (2) | 0.7828 (2) | 0.31144 (10) | 0.0163 (4) | |
C7A | 0.3244 (2) | 0.7215 (2) | 0.35521 (10) | 0.0162 (4) | |
C8A | −0.0543 (2) | 0.6348 (2) | 0.43082 (10) | 0.0163 (4) | |
C9A | −0.0953 (3) | 0.5383 (2) | 0.37990 (11) | 0.0219 (5) | |
H9AA | −0.0378 | 0.5578 | 0.3333 | 0.033* | |
H9AB | −0.2130 | 0.5589 | 0.3818 | 0.033* | |
H9AC | −0.0618 | 0.4356 | 0.3915 | 0.033* | |
C10A | −0.1681 (2) | 0.6701 (2) | 0.49761 (10) | 0.0156 (4) | |
C11A | −0.2985 (2) | 0.5978 (2) | 0.52026 (10) | 0.0184 (4) | |
H11A | −0.3157 | 0.5247 | 0.4917 | 0.022* | |
C12A | −0.4048 (3) | 0.6298 (2) | 0.58367 (11) | 0.0203 (4) | |
H12A | −0.4929 | 0.5790 | 0.5981 | 0.024* | |
C13A | −0.3803 (3) | 0.7363 (2) | 0.62527 (10) | 0.0196 (4) | |
C14A | −0.2529 (3) | 0.8123 (2) | 0.60313 (11) | 0.0204 (4) | |
H14A | −0.2375 | 0.8866 | 0.6314 | 0.025* | |
C15A | −0.1490 (3) | 0.7800 (2) | 0.54017 (10) | 0.0188 (4) | |
H15A | −0.0630 | 0.8331 | 0.5254 | 0.023* | |
C16A | −0.6045 (3) | 0.6997 (3) | 0.71405 (12) | 0.0301 (5) | |
H16A | −0.6595 | 0.7348 | 0.7605 | 0.045* | |
H16B | −0.5628 | 0.5946 | 0.7155 | 0.045* | |
H16C | −0.6821 | 0.7182 | 0.6831 | 0.045* | |
S1B | 0.10878 (6) | 0.65349 (5) | 0.10267 (3) | 0.01748 (12) | |
Cl1B | −0.14593 (6) | 0.14927 (6) | 0.10362 (3) | 0.02510 (13) | |
O1B | 0.34041 (18) | 1.34488 (15) | −0.10641 (7) | 0.0228 (3) | |
N1B | 0.1780 (2) | 0.55835 (17) | 0.22159 (8) | 0.0166 (4) | |
N2B | 0.2536 (2) | 0.78361 (17) | 0.18524 (9) | 0.0168 (4) | |
N3B | 0.2594 (2) | 0.87969 (17) | 0.13039 (8) | 0.0160 (3) | |
C1B | 0.0585 (2) | 0.4861 (2) | 0.13352 (10) | 0.0159 (4) | |
C2B | −0.0169 (2) | 0.3934 (2) | 0.10299 (10) | 0.0183 (4) | |
H2BA | −0.0480 | 0.4159 | 0.0599 | 0.022* | |
C3B | −0.0446 (2) | 0.2665 (2) | 0.13819 (11) | 0.0190 (4) | |
C4B | 0.0026 (2) | 0.2299 (2) | 0.20063 (11) | 0.0197 (4) | |
H4BA | −0.0171 | 0.1411 | 0.2229 | 0.024* | |
C5B | 0.0785 (2) | 0.3235 (2) | 0.23024 (10) | 0.0179 (4) | |
H5BA | 0.1117 | 0.2992 | 0.2728 | 0.022* | |
C6B | 0.1055 (2) | 0.4534 (2) | 0.19703 (10) | 0.0156 (4) | |
C7B | 0.1876 (2) | 0.6651 (2) | 0.17736 (10) | 0.0149 (4) | |
C8B | 0.3288 (2) | 0.9907 (2) | 0.13189 (10) | 0.0148 (4) | |
C9B | 0.4053 (3) | 1.0242 (2) | 0.18983 (11) | 0.0217 (5) | |
H9BA | 0.3489 | 0.9867 | 0.2332 | 0.032* | |
H9BB | 0.3967 | 1.1302 | 0.1935 | 0.032* | |
H9BC | 0.5204 | 0.9777 | 0.1807 | 0.032* | |
C10B | 0.3327 (2) | 1.0871 (2) | 0.07057 (10) | 0.0151 (4) | |
C11B | 0.4141 (2) | 1.2052 (2) | 0.06300 (11) | 0.0183 (4) | |
H11B | 0.4673 | 1.2255 | 0.0983 | 0.022* | |
C12B | 0.4197 (2) | 1.2945 (2) | 0.00492 (11) | 0.0190 (4) | |
H12B | 0.4767 | 1.3740 | 0.0006 | 0.023* | |
C13B | 0.3413 (2) | 1.2662 (2) | −0.04644 (10) | 0.0178 (4) | |
C14B | 0.2581 (2) | 1.1491 (2) | −0.03972 (10) | 0.0176 (4) | |
H14B | 0.2036 | 1.1300 | −0.0748 | 0.021* | |
C15B | 0.2549 (2) | 1.0610 (2) | 0.01764 (10) | 0.0169 (4) | |
H15B | 0.1988 | 0.9809 | 0.0214 | 0.020* | |
C16B | 0.4122 (3) | 1.4732 (2) | −0.11283 (11) | 0.0237 (5) | |
H16D | 0.4099 | 1.5161 | −0.1586 | 0.036* | |
H16E | 0.5253 | 1.4474 | −0.1070 | 0.036* | |
H16F | 0.3507 | 1.5442 | −0.0773 | 0.036* | |
H2NA | 0.174 (3) | 0.622 (2) | 0.3271 (12) | 0.020 (6)* | |
H2NB | 0.317 (3) | 0.776 (3) | 0.2152 (13) | 0.033 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0203 (3) | 0.0234 (2) | 0.0151 (2) | −0.0077 (2) | −0.0040 (2) | −0.0011 (2) |
Cl1A | 0.0276 (3) | 0.0281 (3) | 0.0337 (3) | −0.0151 (2) | −0.0154 (3) | 0.0043 (2) |
O1A | 0.0232 (9) | 0.0330 (8) | 0.0177 (8) | −0.0078 (7) | 0.0016 (7) | −0.0031 (6) |
N1A | 0.0158 (9) | 0.0215 (8) | 0.0153 (8) | −0.0059 (7) | −0.0049 (7) | 0.0014 (7) |
N2A | 0.0173 (9) | 0.0245 (9) | 0.0138 (9) | −0.0071 (7) | −0.0038 (7) | −0.0028 (7) |
N3A | 0.0175 (9) | 0.0219 (8) | 0.0137 (8) | −0.0039 (7) | −0.0039 (7) | 0.0015 (7) |
C1A | 0.0163 (11) | 0.0174 (9) | 0.0190 (10) | −0.0033 (8) | −0.0053 (9) | 0.0028 (8) |
C2A | 0.0241 (12) | 0.0192 (9) | 0.0200 (11) | −0.0059 (8) | −0.0106 (9) | 0.0009 (8) |
C3A | 0.0194 (11) | 0.0188 (9) | 0.0275 (12) | −0.0077 (8) | −0.0136 (10) | 0.0044 (8) |
C4A | 0.0159 (11) | 0.0221 (10) | 0.0239 (11) | −0.0046 (8) | −0.0049 (9) | 0.0043 (8) |
C5A | 0.0197 (11) | 0.0210 (10) | 0.0190 (10) | −0.0044 (8) | −0.0061 (9) | 0.0011 (8) |
C6A | 0.0164 (11) | 0.0166 (9) | 0.0174 (10) | −0.0035 (8) | −0.0066 (9) | 0.0024 (8) |
C7A | 0.0179 (11) | 0.0168 (9) | 0.0155 (10) | −0.0047 (8) | −0.0062 (8) | 0.0019 (8) |
C8A | 0.0179 (11) | 0.0165 (9) | 0.0152 (10) | −0.0033 (8) | −0.0054 (8) | 0.0022 (8) |
C9A | 0.0205 (11) | 0.0258 (11) | 0.0195 (11) | −0.0085 (9) | −0.0001 (9) | −0.0029 (8) |
C10A | 0.0169 (10) | 0.0163 (9) | 0.0147 (10) | −0.0030 (8) | −0.0056 (8) | 0.0021 (8) |
C11A | 0.0212 (11) | 0.0187 (9) | 0.0177 (10) | −0.0071 (8) | −0.0064 (9) | 0.0000 (8) |
C12A | 0.0187 (11) | 0.0236 (10) | 0.0198 (11) | −0.0077 (8) | −0.0035 (9) | 0.0016 (8) |
C13A | 0.0207 (11) | 0.0229 (10) | 0.0147 (10) | −0.0015 (8) | −0.0045 (9) | 0.0011 (8) |
C14A | 0.0218 (12) | 0.0217 (10) | 0.0193 (11) | −0.0053 (8) | −0.0062 (9) | −0.0021 (8) |
C15A | 0.0179 (11) | 0.0207 (10) | 0.0189 (10) | −0.0068 (8) | −0.0037 (9) | 0.0022 (8) |
C16A | 0.0261 (13) | 0.0383 (13) | 0.0229 (12) | −0.0079 (10) | 0.0036 (10) | −0.0006 (10) |
S1B | 0.0189 (3) | 0.0201 (2) | 0.0167 (2) | −0.0083 (2) | −0.0070 (2) | 0.00203 (19) |
Cl1B | 0.0233 (3) | 0.0256 (3) | 0.0293 (3) | −0.0125 (2) | −0.0035 (2) | −0.0085 (2) |
O1B | 0.0315 (9) | 0.0205 (7) | 0.0195 (8) | −0.0110 (6) | −0.0078 (7) | 0.0056 (6) |
N1B | 0.0169 (9) | 0.0182 (8) | 0.0156 (8) | −0.0066 (7) | −0.0023 (7) | −0.0001 (7) |
N2B | 0.0200 (9) | 0.0190 (8) | 0.0152 (9) | −0.0086 (7) | −0.0079 (8) | 0.0020 (7) |
N3B | 0.0162 (9) | 0.0179 (8) | 0.0143 (8) | −0.0035 (7) | −0.0038 (7) | 0.0015 (6) |
C1B | 0.0130 (10) | 0.0180 (9) | 0.0166 (10) | −0.0049 (8) | −0.0007 (8) | −0.0006 (8) |
C2B | 0.0143 (10) | 0.0251 (10) | 0.0158 (10) | −0.0045 (8) | −0.0027 (8) | −0.0028 (8) |
C3B | 0.0143 (10) | 0.0200 (10) | 0.0234 (11) | −0.0063 (8) | −0.0011 (9) | −0.0074 (8) |
C4B | 0.0182 (11) | 0.0164 (9) | 0.0231 (11) | −0.0056 (8) | 0.0015 (9) | −0.0011 (8) |
C5B | 0.0189 (11) | 0.0198 (10) | 0.0149 (10) | −0.0039 (8) | −0.0026 (9) | −0.0009 (8) |
C6B | 0.0125 (10) | 0.0192 (9) | 0.0154 (10) | −0.0047 (8) | −0.0015 (8) | −0.0027 (8) |
C7B | 0.0141 (10) | 0.0193 (9) | 0.0117 (9) | −0.0037 (8) | −0.0030 (8) | −0.0026 (8) |
C8B | 0.0129 (10) | 0.0163 (9) | 0.0153 (10) | −0.0017 (7) | −0.0032 (8) | −0.0033 (7) |
C9B | 0.0287 (12) | 0.0201 (10) | 0.0202 (11) | −0.0081 (9) | −0.0110 (10) | 0.0009 (8) |
C10B | 0.0128 (10) | 0.0156 (9) | 0.0162 (10) | −0.0010 (7) | −0.0026 (8) | −0.0016 (7) |
C11B | 0.0191 (11) | 0.0204 (10) | 0.0188 (10) | −0.0064 (8) | −0.0090 (9) | −0.0011 (8) |
C12B | 0.0200 (11) | 0.0171 (9) | 0.0224 (11) | −0.0082 (8) | −0.0058 (9) | 0.0009 (8) |
C13B | 0.0196 (11) | 0.0164 (9) | 0.0162 (10) | −0.0018 (8) | −0.0022 (9) | 0.0008 (8) |
C14B | 0.0172 (11) | 0.0214 (10) | 0.0165 (10) | −0.0054 (8) | −0.0065 (9) | −0.0037 (8) |
C15B | 0.0161 (10) | 0.0166 (9) | 0.0191 (10) | −0.0052 (8) | −0.0035 (8) | −0.0025 (8) |
C16B | 0.0276 (12) | 0.0216 (10) | 0.0234 (11) | −0.0084 (9) | −0.0063 (10) | 0.0063 (9) |
S1A—C1A | 1.743 (2) | S1B—C1B | 1.748 (2) |
S1A—C7A | 1.757 (2) | S1B—C7B | 1.7610 (19) |
Cl1A—C3A | 1.747 (2) | Cl1B—C3B | 1.746 (2) |
O1A—C13A | 1.369 (2) | O1B—C13B | 1.375 (2) |
O1A—C16A | 1.424 (3) | O1B—C16B | 1.430 (2) |
N1A—C7A | 1.306 (3) | N1B—C7B | 1.305 (2) |
N1A—C6A | 1.399 (2) | N1B—C6B | 1.397 (2) |
N2A—C7A | 1.351 (3) | N2B—C7B | 1.354 (2) |
N2A—N3A | 1.372 (2) | N2B—N3B | 1.382 (2) |
N2A—H2NA | 0.82 (2) | N2B—H2NB | 0.88 (2) |
N3A—C8A | 1.288 (3) | N3B—C8B | 1.286 (2) |
C1A—C2A | 1.393 (3) | C1B—C2B | 1.387 (3) |
C1A—C6A | 1.409 (3) | C1B—C6B | 1.405 (3) |
C2A—C3A | 1.380 (3) | C2B—C3B | 1.383 (3) |
C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
C3A—C4A | 1.392 (3) | C3B—C4B | 1.391 (3) |
C4A—C5A | 1.389 (3) | C4B—C5B | 1.386 (3) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.388 (3) | C5B—C6B | 1.390 (3) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C8A—C10A | 1.478 (3) | C8B—C10B | 1.483 (3) |
C8A—C9A | 1.507 (3) | C8B—C9B | 1.500 (3) |
C9A—H9AA | 0.9800 | C9B—H9BA | 0.9800 |
C9A—H9AB | 0.9800 | C9B—H9BB | 0.9800 |
C9A—H9AC | 0.9800 | C9B—H9BC | 0.9800 |
C10A—C11A | 1.392 (3) | C10B—C11B | 1.392 (3) |
C10A—C15A | 1.401 (3) | C10B—C15B | 1.401 (3) |
C11A—C12A | 1.395 (3) | C11B—C12B | 1.394 (3) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.381 (3) | C12B—C13B | 1.384 (3) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.391 (3) | C13B—C14B | 1.394 (3) |
C14A—C15A | 1.380 (3) | C14B—C15B | 1.377 (3) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—H16A | 0.9800 | C16B—H16D | 0.9800 |
C16A—H16B | 0.9800 | C16B—H16E | 0.9800 |
C16A—H16C | 0.9800 | C16B—H16F | 0.9800 |
C1A—S1A—C7A | 87.78 (10) | C1B—S1B—C7B | 87.71 (9) |
C13A—O1A—C16A | 117.04 (17) | C13B—O1B—C16B | 117.25 (16) |
C7A—N1A—C6A | 109.44 (16) | C7B—N1B—C6B | 109.43 (16) |
C7A—N2A—N3A | 116.12 (17) | C7B—N2B—N3B | 114.82 (16) |
C7A—N2A—H2NA | 119.3 (16) | C7B—N2B—H2NB | 116.7 (16) |
N3A—N2A—H2NA | 124.5 (16) | N3B—N2B—H2NB | 124.5 (16) |
C8A—N3A—N2A | 119.40 (17) | C8B—N3B—N2B | 118.85 (16) |
C2A—C1A—C6A | 121.20 (19) | C2B—C1B—C6B | 121.98 (18) |
C2A—C1A—S1A | 128.43 (16) | C2B—C1B—S1B | 127.89 (15) |
C6A—C1A—S1A | 110.36 (15) | C6B—C1B—S1B | 110.13 (14) |
C3A—C2A—C1A | 117.46 (19) | C3B—C2B—C1B | 116.85 (18) |
C3A—C2A—H2AA | 121.3 | C3B—C2B—H2BA | 121.6 |
C1A—C2A—H2AA | 121.3 | C1B—C2B—H2BA | 121.6 |
C2A—C3A—C4A | 122.45 (19) | C2B—C3B—C4B | 122.57 (18) |
C2A—C3A—Cl1A | 118.53 (16) | C2B—C3B—Cl1B | 118.70 (16) |
C4A—C3A—Cl1A | 119.02 (17) | C4B—C3B—Cl1B | 118.72 (16) |
C5A—C4A—C3A | 119.6 (2) | C5B—C4B—C3B | 119.80 (18) |
C5A—C4A—H4AA | 120.2 | C5B—C4B—H4BA | 120.1 |
C3A—C4A—H4AA | 120.2 | C3B—C4B—H4BA | 120.1 |
C6A—C5A—C4A | 119.44 (19) | C4B—C5B—C6B | 119.26 (18) |
C6A—C5A—H5AA | 120.3 | C4B—C5B—H5BA | 120.4 |
C4A—C5A—H5AA | 120.3 | C6B—C5B—H5BA | 120.4 |
C5A—C6A—N1A | 125.37 (18) | C5B—C6B—N1B | 125.19 (17) |
C5A—C6A—C1A | 119.75 (18) | C5B—C6B—C1B | 119.52 (17) |
N1A—C6A—C1A | 114.88 (18) | N1B—C6B—C1B | 115.29 (17) |
N1A—C7A—N2A | 123.88 (18) | N1B—C7B—N2B | 124.37 (17) |
N1A—C7A—S1A | 117.51 (15) | N1B—C7B—S1B | 117.43 (15) |
N2A—C7A—S1A | 118.62 (15) | N2B—C7B—S1B | 118.20 (14) |
N3A—C8A—C10A | 115.50 (17) | N3B—C8B—C10B | 115.59 (17) |
N3A—C8A—C9A | 124.95 (18) | N3B—C8B—C9B | 124.27 (18) |
C10A—C8A—C9A | 119.54 (18) | C10B—C8B—C9B | 120.13 (17) |
C8A—C9A—H9AA | 109.5 | C8B—C9B—H9BA | 109.5 |
C8A—C9A—H9AB | 109.5 | C8B—C9B—H9BB | 109.5 |
H9AA—C9A—H9AB | 109.5 | H9BA—C9B—H9BB | 109.5 |
C8A—C9A—H9AC | 109.5 | C8B—C9B—H9BC | 109.5 |
H9AA—C9A—H9AC | 109.5 | H9BA—C9B—H9BC | 109.5 |
H9AB—C9A—H9AC | 109.5 | H9BB—C9B—H9BC | 109.5 |
C11A—C10A—C15A | 117.53 (18) | C11B—C10B—C15B | 117.61 (18) |
C11A—C10A—C8A | 121.86 (18) | C11B—C10B—C8B | 121.75 (17) |
C15A—C10A—C8A | 120.60 (18) | C15B—C10B—C8B | 120.64 (17) |
C10A—C11A—C12A | 121.87 (19) | C10B—C11B—C12B | 121.71 (18) |
C10A—C11A—H11A | 119.1 | C10B—C11B—H11B | 119.1 |
C12A—C11A—H11A | 119.1 | C12B—C11B—H11B | 119.1 |
C13A—C12A—C11A | 119.2 (2) | C13B—C12B—C11B | 119.36 (19) |
C13A—C12A—H12A | 120.4 | C13B—C12B—H12B | 120.3 |
C11A—C12A—H12A | 120.4 | C11B—C12B—H12B | 120.3 |
O1A—C13A—C12A | 124.9 (2) | O1B—C13B—C12B | 124.65 (18) |
O1A—C13A—C14A | 115.11 (18) | O1B—C13B—C14B | 115.44 (17) |
C12A—C13A—C14A | 120.01 (19) | C12B—C13B—C14B | 119.91 (18) |
C15A—C14A—C13A | 120.20 (19) | C15B—C14B—C13B | 120.10 (18) |
C15A—C14A—H14A | 119.9 | C15B—C14B—H14B | 119.9 |
C13A—C14A—H14A | 119.9 | C13B—C14B—H14B | 119.9 |
C14A—C15A—C10A | 121.12 (19) | C14B—C15B—C10B | 121.31 (19) |
C14A—C15A—H15A | 119.4 | C14B—C15B—H15B | 119.3 |
C10A—C15A—H15A | 119.4 | C10B—C15B—H15B | 119.3 |
O1A—C16A—H16A | 109.5 | O1B—C16B—H16D | 109.5 |
O1A—C16A—H16B | 109.5 | O1B—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
O1A—C16A—H16C | 109.5 | O1B—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
C7A—N2A—N3A—C8A | −176.68 (17) | C7B—N2B—N3B—C8B | −176.02 (17) |
C7A—S1A—C1A—C2A | 176.79 (18) | C7B—S1B—C1B—C2B | 179.72 (19) |
C7A—S1A—C1A—C6A | −1.74 (14) | C7B—S1B—C1B—C6B | −0.13 (15) |
C6A—C1A—C2A—C3A | −0.9 (3) | C6B—C1B—C2B—C3B | 0.2 (3) |
S1A—C1A—C2A—C3A | −179.33 (15) | S1B—C1B—C2B—C3B | −179.58 (15) |
C1A—C2A—C3A—C4A | −1.1 (3) | C1B—C2B—C3B—C4B | −1.2 (3) |
C1A—C2A—C3A—Cl1A | 178.88 (14) | C1B—C2B—C3B—Cl1B | 177.64 (15) |
C2A—C3A—C4A—C5A | 1.6 (3) | C2B—C3B—C4B—C5B | 1.0 (3) |
Cl1A—C3A—C4A—C5A | −178.44 (15) | Cl1B—C3B—C4B—C5B | −177.90 (15) |
C3A—C4A—C5A—C6A | 0.1 (3) | C3B—C4B—C5B—C6B | 0.3 (3) |
C4A—C5A—C6A—N1A | 176.79 (17) | C4B—C5B—C6B—N1B | 178.88 (18) |
C4A—C5A—C6A—C1A | −2.1 (3) | C4B—C5B—C6B—C1B | −1.2 (3) |
C7A—N1A—C6A—C5A | 179.64 (18) | C7B—N1B—C6B—C5B | 178.79 (19) |
C7A—N1A—C6A—C1A | −1.4 (2) | C7B—N1B—C6B—C1B | −1.1 (2) |
C2A—C1A—C6A—C5A | 2.5 (3) | C2B—C1B—C6B—C5B | 1.0 (3) |
S1A—C1A—C6A—C5A | −178.81 (14) | S1B—C1B—C6B—C5B | −179.17 (15) |
C2A—C1A—C6A—N1A | −176.44 (17) | C2B—C1B—C6B—N1B | −179.14 (18) |
S1A—C1A—C6A—N1A | 2.2 (2) | S1B—C1B—C6B—N1B | 0.7 (2) |
C6A—N1A—C7A—N2A | −179.93 (17) | C6B—N1B—C7B—N2B | −179.15 (18) |
C6A—N1A—C7A—S1A | 0.0 (2) | C6B—N1B—C7B—S1B | 1.0 (2) |
N3A—N2A—C7A—N1A | −175.47 (17) | N3B—N2B—C7B—N1B | 176.61 (18) |
N3A—N2A—C7A—S1A | 4.6 (2) | N3B—N2B—C7B—S1B | −3.5 (2) |
C1A—S1A—C7A—N1A | 1.05 (15) | C1B—S1B—C7B—N1B | −0.52 (16) |
C1A—S1A—C7A—N2A | −179.01 (16) | C1B—S1B—C7B—N2B | 179.61 (16) |
N2A—N3A—C8A—C10A | −177.94 (15) | N2B—N3B—C8B—C10B | 178.92 (16) |
N2A—N3A—C8A—C9A | 2.8 (3) | N2B—N3B—C8B—C9B | 0.0 (3) |
N3A—C8A—C10A—C11A | −168.14 (17) | N3B—C8B—C10B—C11B | −175.29 (18) |
C9A—C8A—C10A—C11A | 11.1 (3) | C9B—C8B—C10B—C11B | 3.6 (3) |
N3A—C8A—C10A—C15A | 12.7 (3) | N3B—C8B—C10B—C15B | 4.1 (3) |
C9A—C8A—C10A—C15A | −168.03 (17) | C9B—C8B—C10B—C15B | −176.92 (18) |
C15A—C10A—C11A—C12A | −1.6 (3) | C15B—C10B—C11B—C12B | −0.4 (3) |
C8A—C10A—C11A—C12A | 179.18 (18) | C8B—C10B—C11B—C12B | 179.09 (18) |
C10A—C11A—C12A—C13A | 0.1 (3) | C10B—C11B—C12B—C13B | 0.5 (3) |
C16A—O1A—C13A—C12A | −0.6 (3) | C16B—O1B—C13B—C12B | −6.4 (3) |
C16A—O1A—C13A—C14A | −179.99 (17) | C16B—O1B—C13B—C14B | 174.81 (17) |
C11A—C12A—C13A—O1A | −178.03 (18) | C11B—C12B—C13B—O1B | −178.90 (18) |
C11A—C12A—C13A—C14A | 1.3 (3) | C11B—C12B—C13B—C14B | −0.1 (3) |
O1A—C13A—C14A—C15A | 178.31 (17) | O1B—C13B—C14B—C15B | 178.42 (17) |
C12A—C13A—C14A—C15A | −1.1 (3) | C12B—C13B—C14B—C15B | −0.5 (3) |
C13A—C14A—C15A—C10A | −0.5 (3) | C13B—C14B—C15B—C10B | 0.7 (3) |
C11A—C10A—C15A—C14A | 1.9 (3) | C11B—C10B—C15B—C14B | −0.2 (3) |
C8A—C10A—C15A—C14A | −178.95 (17) | C8B—C10B—C15B—C14B | −179.70 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···N1B | 0.82 (2) | 2.18 (2) | 2.974 (2) | 162 (2) |
N2B—H2NB···N1A | 0.88 (3) | 2.13 (3) | 2.983 (2) | 166 (3) |
Experimental details
Crystal data | |
Chemical formula | C16H14ClN3OS |
Mr | 331.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.5294 (1), 9.3097 (1), 19.8115 (3) |
α, β, γ (°) | 87.999 (1), 78.091 (1), 79.461 (1) |
V (Å3) | 1513.32 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.25 × 0.20 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.908, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31608, 6907, 5393 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.088, 1.03 |
No. of reflections | 6907 |
No. of parameters | 409 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.40 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···N1B | 0.82 (2) | 2.18 (2) | 2.974 (2) | 162 (2) |
N2B—H2NB···N1A | 0.88 (3) | 2.13 (3) | 2.983 (2) | 166 (3) |
Acknowledgements
The authors thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). BKS gratefully acknowledges the Department of Atomic Energy (DAE)/BRNS, Government of India, for providing financial assistance in the BRNS Project (No. 2011/34/20-BRNS/0846).
References
Ali, H., Khamis, N. A. & Yamin, B. M. (2004). Acta Cryst. E60, o1873–o1874. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dutkiewicz, G., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o874. Web of Science CrossRef IUCr Journals Google Scholar
Fouda, A. S., Mostafa, H. A., Ghazy, S. E. & El-Farah, S. A. (2007). Int. J. Electrochem. Sci. 2, 182–194. CAS Google Scholar
Fun, H.-K., Quah, C. K., Munirajasekhar, D., Himaja, M. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2438–o2439. CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Sarojini, B. K., Mohan, B. J. & Narayana, B. (2012b). Acta Cryst. E68, o2459. CSD CrossRef IUCr Journals Google Scholar
Naseema, K., Sujith, K. V., Manjunatha, K. B., Kalluraya, B., Umesh, G. & Rao, V. (2010). Opt. Laser Technol. 42, 741–748. Web of Science CrossRef CAS Google Scholar
Rollas, S. & Küçükgüzel, S. G. (2007). Molecules, 12, 1910–1939. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeb, A. & Yousuf, S. (2011). Acta Cryst. E67, o2801. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Hydrazones and their derivatives constitute a versatile class of compounds in organic chemistry. Recently, a lot of biologically important hydrazone derivatives with a number of functional groups have been synthesized. These compounds showed biological properties such as anticonvulsant, antidepressant, analgesic, antiinflammatory and antiplatelet activities (Rollas & Küçükgüzel, 2007). Hydrazone derivatives could be used in optical limiters and optical switches due to their optical limiting property (Naseema et al., 2010). Hydrazone derivatives also act as corrosion inhibitors (Fouda et al., 2007). Structures related to hydrazone derivatives have been reported (Dutkiewicz et al., 2010; Ali et al., 2004; Zeb & Yousuf, 2011). The present work describes the synthesis and crystal structure of the title compound, (I), prepared by the condensation of 1-(6-chloro1,3-benzothiazol-2-yl) hydrazine with 4-methoxyacetophenone in ethanol.
The asymmetric unit of (I) consists of two independent molecules, A and B, respectively (Fig. 1), with comparable geometries. In molecule A, the 1,3-benzothiazol-2-yl ring system (S1A/N1A/C1A–C7A, r.m.s. deviation = 0.029 Å) forms a dihedral angle of 17.08 (8)° with the benzene ring (C10A–C15A). The corresponding r.m.s. deviation and dihedral angle for molecule B are 0.010 Å and 8.63 (7)°, respectively. Bond lengths and angles are within normal ranges and are comparable with those observed in the related structures (Fun et al., 2012a,b).
In the crystal structure, molecules A and B are interlinked via intermolecular N2A–H2NA···N1B and N2B–H2NB···N1A hydrogen bonds (Table 1) into dimers.