Related literature
For the synthesis of the compound, see: Auwers (1909
).
Experimental
Crystal data
C13H11ClN2O Mr = 246.69 Orthorhombic, P b c a a = 10.7590 (1) Å b = 7.3189 (1) Å c = 28.9222 (3) Å V = 2277.45 (4) Å3 Z = 8 Mo Kα radiation μ = 0.32 mm−1 T = 100 K 0.25 × 0.25 × 0.15 mm
|
Data collection
Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) Tmin = 0.925, Tmax = 0.954 20107 measured reflections 2614 independent reflections 2326 reflections with I > 2σ(I) Rint = 0.033
|
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | O1—H1⋯N1 | 0.84 (2) | 1.88 (2) | 2.6382 (13) | 149.8 (19) | N2—H2⋯Cg1i | 0.859 (18) | 2.73 (2) | 3.3675 (12) | 132.3 (17) | Symmetry code: (i) . | |
Data collection: APEX2 (Bruker, 2009
); cell refinement: SAINT (Bruker, 2009
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: X-SEED (Barbour, 2001
); software used to prepare material for publication: publCIF (Westrip, 2010
).
Supporting information
Salicylaldehyde (1 ml, 10 mmol) and 4-chlorophenylhydrazine hydrochloride (1.8 g, 10 mmol) were dissolved in ethanol (100 ml). No HCl-abstracting reagent was added. The solution was heated for an hour. Slow evaporation of the solvent gave colorless crystals of the Schiff base.
Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 times Ueq(C). The amino and hydroxy H atoms were located in a difference Fourier map, and were freely refined.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
2-{[2-(4-Chlorophenyl)hydrazinylidene]methyl}phenol
top Crystal data top C13H11ClN2O | F(000) = 1024 |
Mr = 246.69 | Dx = 1.439 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 7363 reflections |
a = 10.7590 (1) Å | θ = 2.4–28.3° |
b = 7.3189 (1) Å | µ = 0.32 mm−1 |
c = 28.9222 (3) Å | T = 100 K |
V = 2277.45 (4) Å3 | Block, colorless |
Z = 8 | 0.25 × 0.25 × 0.15 mm |
Data collection top Bruker SMART APEX diffractometer | 2614 independent reflections |
Radiation source: fine-focus sealed tube | 2326 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.925, Tmax = 0.954 | k = −9→9 |
20107 measured reflections | l = −37→37 |
Refinement top 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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.9769P] where P = (Fo2 + 2Fc2)/3 |
2614 reflections | (Δ/σ)max = 0.001 |
162 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top C13H11ClN2O | V = 2277.45 (4) Å3 |
Mr = 246.69 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.7590 (1) Å | µ = 0.32 mm−1 |
b = 7.3189 (1) Å | T = 100 K |
c = 28.9222 (3) Å | 0.25 × 0.25 × 0.15 mm |
Data collection top Bruker SMART APEX diffractometer | 2614 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2326 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 0.954 | Rint = 0.033 |
20107 measured reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.37 e Å−3 |
2614 reflections | Δρmin = −0.19 e Å−3 |
162 parameters | |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.72028 (3) | 0.56809 (4) | 0.484943 (10) | 0.02413 (12) | |
O1 | 0.75260 (9) | 0.62244 (14) | 0.75810 (3) | 0.0202 (2) | |
N1 | 0.57723 (9) | 0.76810 (14) | 0.70608 (3) | 0.0160 (2) | |
N2 | 0.52407 (10) | 0.81449 (15) | 0.66514 (4) | 0.0192 (2) | |
C1 | 0.68256 (11) | 0.67666 (16) | 0.79476 (4) | 0.0158 (2) | |
C2 | 0.72583 (11) | 0.63711 (18) | 0.83900 (4) | 0.0183 (3) | |
H2A | 0.8022 | 0.5739 | 0.8429 | 0.022* | |
C3 | 0.65750 (12) | 0.68996 (16) | 0.87755 (4) | 0.0197 (3) | |
H3 | 0.6883 | 0.6646 | 0.9077 | 0.024* | |
C4 | 0.54397 (12) | 0.77994 (17) | 0.87237 (4) | 0.0198 (3) | |
H4 | 0.4971 | 0.8152 | 0.8987 | 0.024* | |
C5 | 0.50049 (12) | 0.81715 (16) | 0.82826 (4) | 0.0174 (2) | |
H5 | 0.4230 | 0.8778 | 0.8247 | 0.021* | |
C6 | 0.56790 (11) | 0.76755 (16) | 0.78874 (4) | 0.0150 (2) | |
C7 | 0.51856 (11) | 0.81180 (16) | 0.74331 (4) | 0.0157 (2) | |
H7 | 0.4414 | 0.8743 | 0.7410 | 0.019* | |
C8 | 0.57272 (11) | 0.75285 (16) | 0.62353 (4) | 0.0157 (2) | |
C9 | 0.50203 (11) | 0.77689 (17) | 0.58344 (4) | 0.0183 (3) | |
H9 | 0.4223 | 0.8322 | 0.5854 | 0.022* | |
C10 | 0.54686 (12) | 0.72102 (17) | 0.54082 (4) | 0.0193 (3) | |
H10 | 0.4986 | 0.7382 | 0.5137 | 0.023* | |
C11 | 0.66308 (12) | 0.63963 (17) | 0.53830 (4) | 0.0180 (2) | |
C12 | 0.73438 (12) | 0.61342 (17) | 0.57764 (4) | 0.0182 (3) | |
H12 | 0.8137 | 0.5569 | 0.5754 | 0.022* | |
C13 | 0.68960 (11) | 0.66998 (16) | 0.62040 (4) | 0.0171 (2) | |
H13 | 0.7383 | 0.6524 | 0.6474 | 0.020* | |
H1 | 0.7170 (18) | 0.662 (3) | 0.7343 (7) | 0.047 (6)* | |
H2 | 0.4532 (17) | 0.868 (3) | 0.6662 (6) | 0.032 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0330 (2) | 0.02229 (18) | 0.01713 (17) | 0.00084 (13) | 0.00504 (12) | −0.00208 (11) |
O1 | 0.0173 (4) | 0.0242 (5) | 0.0191 (5) | 0.0049 (4) | 0.0013 (4) | −0.0008 (4) |
N1 | 0.0172 (5) | 0.0153 (5) | 0.0154 (5) | −0.0010 (4) | −0.0023 (4) | 0.0006 (4) |
N2 | 0.0184 (5) | 0.0240 (6) | 0.0152 (5) | 0.0063 (4) | −0.0014 (4) | 0.0001 (4) |
C1 | 0.0158 (6) | 0.0126 (5) | 0.0189 (6) | −0.0020 (4) | 0.0007 (4) | −0.0014 (4) |
C2 | 0.0186 (6) | 0.0145 (6) | 0.0218 (6) | −0.0009 (5) | −0.0036 (5) | 0.0005 (5) |
C3 | 0.0260 (6) | 0.0158 (6) | 0.0171 (6) | −0.0041 (5) | −0.0036 (5) | 0.0014 (4) |
C4 | 0.0250 (6) | 0.0177 (6) | 0.0166 (6) | −0.0040 (5) | 0.0034 (5) | −0.0009 (5) |
C5 | 0.0172 (6) | 0.0143 (5) | 0.0208 (6) | −0.0004 (5) | 0.0026 (5) | −0.0005 (4) |
C6 | 0.0155 (5) | 0.0121 (5) | 0.0174 (6) | −0.0022 (4) | −0.0004 (4) | 0.0000 (4) |
C7 | 0.0141 (6) | 0.0133 (5) | 0.0195 (6) | −0.0001 (4) | 0.0002 (4) | 0.0005 (4) |
C8 | 0.0170 (6) | 0.0139 (5) | 0.0162 (6) | −0.0025 (4) | 0.0007 (4) | 0.0012 (4) |
C9 | 0.0166 (6) | 0.0185 (6) | 0.0199 (6) | 0.0001 (5) | −0.0021 (5) | 0.0012 (5) |
C10 | 0.0217 (6) | 0.0194 (6) | 0.0169 (6) | −0.0022 (5) | −0.0033 (5) | 0.0010 (5) |
C11 | 0.0241 (6) | 0.0152 (5) | 0.0147 (5) | −0.0024 (5) | 0.0038 (5) | −0.0010 (4) |
C12 | 0.0185 (6) | 0.0153 (6) | 0.0210 (6) | 0.0008 (5) | 0.0024 (5) | 0.0024 (5) |
C13 | 0.0175 (6) | 0.0167 (6) | 0.0171 (6) | −0.0006 (5) | −0.0016 (4) | 0.0022 (4) |
Geometric parameters (Å, º) top Cl1—C11 | 1.7418 (12) | C5—C6 | 1.4014 (16) |
O1—C1 | 1.3600 (15) | C5—H5 | 0.9500 |
O1—H1 | 0.84 (2) | C6—C7 | 1.4539 (16) |
N1—C7 | 1.2883 (15) | C7—H7 | 0.9500 |
N1—N2 | 1.3580 (14) | C8—C9 | 1.3978 (16) |
N2—C8 | 1.3878 (15) | C8—C13 | 1.3991 (17) |
N2—H2 | 0.859 (18) | C9—C10 | 1.3855 (17) |
C1—C2 | 1.3919 (17) | C9—H9 | 0.9500 |
C1—C6 | 1.4123 (17) | C10—C11 | 1.3870 (18) |
C2—C3 | 1.3905 (18) | C10—H10 | 0.9500 |
C2—H2A | 0.9500 | C11—C12 | 1.3857 (18) |
C3—C4 | 1.3958 (19) | C12—C13 | 1.3901 (17) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C4—C5 | 1.3859 (17) | C13—H13 | 0.9500 |
C4—H4 | 0.9500 | | |
| | | |
C1—O1—H1 | 106.7 (14) | C1—C6—C7 | 122.36 (11) |
C7—N1—N2 | 117.40 (10) | N1—C7—C6 | 121.41 (11) |
N1—N2—C8 | 121.06 (10) | N1—C7—H7 | 119.3 |
N1—N2—H2 | 117.2 (11) | C6—C7—H7 | 119.3 |
C8—N2—H2 | 121.0 (11) | N2—C8—C9 | 118.24 (11) |
O1—C1—C2 | 118.08 (11) | N2—C8—C13 | 122.42 (11) |
O1—C1—C6 | 121.69 (11) | C9—C8—C13 | 119.33 (11) |
C2—C1—C6 | 120.22 (11) | C10—C9—C8 | 120.76 (11) |
C1—C2—C3 | 120.17 (11) | C10—C9—H9 | 119.6 |
C1—C2—H2A | 119.9 | C8—C9—H9 | 119.6 |
C3—C2—H2A | 119.9 | C9—C10—C11 | 119.17 (11) |
C2—C3—C4 | 120.51 (11) | C9—C10—H10 | 120.4 |
C2—C3—H3 | 119.7 | C11—C10—H10 | 120.4 |
C4—C3—H3 | 119.7 | C10—C11—C12 | 121.02 (11) |
C5—C4—C3 | 119.15 (11) | C10—C11—Cl1 | 119.62 (9) |
C5—C4—H4 | 120.4 | C12—C11—Cl1 | 119.36 (10) |
C3—C4—H4 | 120.4 | C11—C12—C13 | 119.83 (12) |
C4—C5—C6 | 121.68 (11) | C11—C12—H12 | 120.1 |
C4—C5—H5 | 119.2 | C13—C12—H12 | 120.1 |
C6—C5—H5 | 119.2 | C12—C13—C8 | 119.88 (11) |
C5—C6—C1 | 118.27 (11) | C12—C13—H13 | 120.1 |
C5—C6—C7 | 119.37 (11) | C8—C13—H13 | 120.1 |
| | | |
C7—N1—N2—C8 | −171.80 (11) | C1—C6—C7—N1 | 0.68 (18) |
O1—C1—C2—C3 | 179.94 (11) | N1—N2—C8—C9 | 168.57 (11) |
C6—C1—C2—C3 | −1.21 (19) | N1—N2—C8—C13 | −12.10 (18) |
C1—C2—C3—C4 | 1.21 (19) | N2—C8—C9—C10 | 178.83 (12) |
C2—C3—C4—C5 | −0.44 (18) | C13—C8—C9—C10 | −0.52 (18) |
C3—C4—C5—C6 | −0.32 (18) | C8—C9—C10—C11 | 0.32 (19) |
C4—C5—C6—C1 | 0.31 (18) | C9—C10—C11—C12 | 0.10 (19) |
C4—C5—C6—C7 | −179.31 (11) | C9—C10—C11—Cl1 | 179.78 (10) |
O1—C1—C6—C5 | 179.26 (11) | C10—C11—C12—C13 | −0.30 (19) |
C2—C1—C6—C5 | 0.46 (18) | Cl1—C11—C12—C13 | −179.99 (10) |
O1—C1—C6—C7 | −1.13 (18) | C11—C12—C13—C8 | 0.10 (18) |
C2—C1—C6—C7 | −179.93 (11) | N2—C8—C13—C12 | −179.01 (11) |
N2—N1—C7—C6 | 179.85 (10) | C9—C8—C13—C12 | 0.31 (18) |
C5—C6—C7—N1 | −179.72 (11) | | |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C1–C6 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 (2) | 1.88 (2) | 2.6382 (13) | 149.8 (19) |
N2—H2···Cg1i | 0.859 (18) | 2.73 (2) | 3.3675 (12) | 132.3 (17) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data |
Chemical formula | C13H11ClN2O |
Mr | 246.69 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 100 |
a, b, c (Å) | 10.7590 (1), 7.3189 (1), 28.9222 (3) |
V (Å3) | 2277.45 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.25 × 0.25 × 0.15 |
|
Data collection |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.925, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20107, 2614, 2326 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.089, 1.04 |
No. of reflections | 2614 |
No. of parameters | 162 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.19 |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C1–C6 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 (2) | 1.88 (2) | 2.6382 (13) | 149.8 (19) |
N2—H2···Cg1i | 0.859 (18) | 2.73 (2) | 3.3675 (12) | 132.3 (17) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
Acknowledgements
We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.
References
Auwers, K. (1909). Justus Liebigs Ann. Chem. 365, 314–342. CrossRef CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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 | CRYSTALLOGRAPHIC COMMUNICATIONS |
ISSN: 2056-9890
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access
There in a enormous amount of literature on Schiff bases, which are synthesized by reaction of a primary amine with a carbonyl function. The synthesis of the title hydrazone (Scheme I) was reported a century ago (Auwers, 1909). The C13H11ClN2O molecule (Scheme I) is twisted along the –CH═N–NH– portion that connects the two aromatic rings. The non-hydrogen atoms approximately lie on plane (r.m.s. deviation 0.115 Å), the rings being twisted by 9.36 (3)°. The hydroxy group is hydrogen-bond donor the the azomethine N atom (Fig. 1). The amino H atom is involved in the N—H···π interaction in the crystal structure (Table 1).