organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-[(1E)-5-(3-Chloro­phen­yl)-3-methyl­cyclo­hex-2-en-1-yl­­idene]hydroxyl­amine

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, bDepartment of Chemistry, Saveetha Engineering College, Chennai, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: a_sp59@yahoo.in

(Received 8 November 2012; accepted 18 February 2013; online 28 February 2013)

The whole of the title mol­ecule, C13H14ClNO, is disordered over two sets of sites with a refined occupancy ratio of 0.560 (6):0.440 (6). The oxime group having a C=N double bond adopts an E conformation. The dihedral angles between the rings (all atoms) are 89.5 (5) (major componenent) and 88.0 (6)° (minor component).

Related literature

For applications of oximes, see: Kukushkin et al. (1996[Kukushkin, V. Yu., Tudela, D. & Pombeiro, A. J. L. (1996). Coord. Chem. Rev. 156, 333-362.]): Chaudhuri (2003[Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143-168.]). For a related structure of a chloro­phenyl oxime derivative, see: Ravichandran et al. (2010[Ravichandran, K., Ramesh, P., Rani, M., Kabilan, S. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o1506.]).

[Scheme 1]

Experimental

Crystal data
  • C13H14ClNO

  • Mr = 235.70

  • Tetragonal, I 41 /a

  • a = 19.7898 (8) Å

  • c = 12.4416 (11) Å

  • V = 4872.6 (5) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 295 K

  • 0.25 × 0.22 × 0.19 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.930, Tmax = 0.946

  • 19841 measured reflections

  • 2394 independent reflections

  • 1765 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.080

  • wR(F2) = 0.242

  • S = 1.05

  • 2394 reflections

  • 255 parameters

  • 93 restraints

  • H-atom parameters constrained

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Oximes are a classical type of chelating ligands which are widely used in coordination and analytical chemistry (Kukushkin et al., 1996; Chaudhuri, 2003).

The bond lengths and bond angles of the title compound are comparable with those observed in other chlorophenyl oxime derivative. (Ravichandran et al., 2010). The whole molecule of the title compound is disordered over two positions (Fig. 1 and 2) with a refined occupancy ratio of 0.560:0.440 (6). For the major disorder componenent, the phenyl ring [C8—C13] is almost perpendicular to the cyclohexene ring [C1—C6] with dihedral angle 89.5 (5) °. Similarly, for the minor disorder component, the phenyl ring [C8'-C13'] is almost perpendicular to the cyclohexene ring [C1'-C6'] with dihedral angle 88.0 (6) °. In the crystal unit, the oxime groups C2=N1 and C2'=N1' double bond exists in E configuration, which is confirmed by the torsion angle of -177.7 (2) and 177.0 (2)° of C3—C2—N1—O1 and C3'-C2'-N1'-O1' moeity respectively. Phenyl ring is completely planar, while cyclohexene ring is far from being planar with maximum deviations from the mean plane being 0.195 (2) and 0.241 (7) Å for the C1 and C6' atoms respectively.

Related literature top

For applications of oximes, see: Kukushkin et al. (1996): Chaudhuri (2003). For a related structure of a chlorophenyl oxime derivative, see: Ravichandran et al. (2010).

Experimental top

To a stirred suspension of benzo[c]furan (2.38 g, 7.437 mmol) in dry THF (20 ml), lead tetraacetate (3.2 g, 7.437 mmol) was added and refluxed at 50°C for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2 x 20 ml), washed with brine solution and dried (Na2SO4). The removal of solvent in vacuo followed by crystallization from methanol afforded the title compound as a colorless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Refinement top

The whole molecule was disordered over two sites (C1—C13/Cl/N1/O1 and C1'-C13'/Cl'/N1'/O1') with refined occupancy ratio 0.560:0.440 (6). Displacement ellipsoid and bond distance similarity restraints were employed to control the geometry of both disorder components. The residual factors are R1 = 0.0803 and wR2 = 0.2417 are rather high. The data were collected with the body centred tetragonal cell as the Bravais cell and processed in the Laue class 4/m. The multiscan absorption correction was done assuming in the crystal to be medium absorber. The residual factors are high, probably due to the restraints needed to account for completely disordered molecule. The actual disorder probably could be several fold with each having slightly different orientation. The idealized two fold disorder may not be accounting for the full disorder. All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed in the range 0.93–0.97 Å with Uiso(H) = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the major component of title compound with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Stick plot of both major and minor components of the title compound with atom labels for non-H atoms.
N-[(1E)-5-(3-Chlorophenyl)-3-methylcyclohex-2-en-1-ylidene]hydroxylamine top
Crystal data top
C13H14ClNODx = 1.285 Mg m3
Mr = 235.70Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 2394 reflections
Hall symbol: -I 4adθ = 1.5–26.0°
a = 19.7898 (8) ŵ = 0.29 mm1
c = 12.4416 (11) ÅT = 295 K
V = 4872.6 (5) Å3Block, white
Z = 160.25 × 0.22 × 0.19 mm
F(000) = 1984
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2394 independent reflections
Radiation source: fine-focus sealed tube1765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and ϕ scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2424
Tmin = 0.930, Tmax = 0.946k = 2424
19841 measured reflectionsl = 1515
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)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.242H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1164P)2 + 10.7128P]
where P = (Fo2 + 2Fc2)/3
2394 reflections(Δ/σ)max = 0.026
255 parametersΔρmax = 0.72 e Å3
93 restraintsΔρmin = 0.50 e Å3
Crystal data top
C13H14ClNOZ = 16
Mr = 235.70Mo Kα radiation
Tetragonal, I41/aµ = 0.29 mm1
a = 19.7898 (8) ÅT = 295 K
c = 12.4416 (11) Å0.25 × 0.22 × 0.19 mm
V = 4872.6 (5) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2394 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1765 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.946Rint = 0.034
19841 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08093 restraints
wR(F2) = 0.242H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1164P)2 + 10.7128P]
where P = (Fo2 + 2Fc2)/3
2394 reflectionsΔρmax = 0.72 e Å3
255 parametersΔρmin = 0.50 e Å3
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.5714 (9)0.6964 (10)0.5126 (13)0.064 (4)0.560 (6)
H10.58730.71760.56320.095*0.560 (6)
N10.5172 (8)0.6572 (8)0.5484 (11)0.055 (4)0.560 (6)
C10.5202 (8)0.6216 (9)0.3560 (9)0.053 (4)0.560 (6)
H1A0.56870.62830.35890.064*0.560 (6)
H1B0.50100.65820.31410.064*0.560 (6)
C20.4922 (8)0.6246 (8)0.4677 (7)0.036 (3)0.560 (6)
C30.4336 (8)0.5833 (7)0.4904 (12)0.044 (4)0.560 (6)
H30.41350.58710.55770.053*0.560 (6)
C40.4070 (6)0.5404 (6)0.4205 (13)0.043 (3)0.560 (6)
C50.4409 (10)0.5208 (11)0.3142 (15)0.055 (5)0.560 (6)
H5A0.44800.47230.31280.067*0.560 (6)
H5B0.41110.53230.25500.067*0.560 (6)
C60.5054 (4)0.5550 (4)0.2999 (5)0.0570 (18)0.560 (6)
H60.53770.52380.33310.068*0.560 (6)
C70.34307 (17)0.49939 (17)0.4407 (3)0.057 (2)0.560 (6)
H7A0.33380.47150.37930.085*0.560 (6)
H7B0.30580.52950.45270.085*0.560 (6)
H7C0.34940.47130.50280.085*0.560 (6)
C80.52861 (17)0.55769 (17)0.1822 (3)0.0421 (17)0.560 (6)
C90.58200 (17)0.51926 (17)0.1431 (3)0.0541 (19)0.560 (6)
H90.60540.49040.18880.065*0.560 (6)
C100.60045 (17)0.52400 (17)0.0355 (3)0.063 (3)0.560 (6)
C110.56550 (17)0.56717 (17)0.0328 (3)0.066 (3)0.560 (6)
H110.57780.57030.10480.080*0.560 (6)
C120.51211 (17)0.60561 (17)0.0063 (3)0.057 (2)0.560 (6)
H120.48870.63450.03950.069*0.560 (6)
C130.49367 (17)0.60087 (17)0.1138 (3)0.055 (2)0.560 (6)
H130.45800.62660.14000.066*0.560 (6)
Cl10.6641 (5)0.4726 (6)0.0028 (7)0.105 (2)0.560 (6)
O1'0.5722 (9)0.6919 (14)0.5195 (19)0.072 (7)0.440 (6)
H1'0.57860.71900.56820.108*0.440 (6)
N1'0.5138 (8)0.6543 (11)0.5411 (14)0.049 (5)0.440 (6)
C1'0.5283 (9)0.6052 (12)0.3642 (11)0.054 (5)0.440 (6)
H1'10.56380.57130.36500.064*0.440 (6)
H1'20.54910.64840.34850.064*0.440 (6)
C2'0.4964 (11)0.6083 (10)0.4731 (9)0.039 (4)0.440 (6)
C3'0.4381 (9)0.5666 (9)0.4972 (14)0.036 (3)0.440 (6)
H3'0.41830.57040.56470.043*0.440 (6)
C4'0.4117 (7)0.5234 (8)0.4276 (16)0.040 (3)0.440 (6)
C5'0.4337 (12)0.5340 (13)0.3107 (17)0.049 (4)0.440 (6)
H5'10.45480.49210.28800.059*0.440 (6)
H5'20.39260.53840.26890.059*0.440 (6)
C6'0.4783 (3)0.5882 (4)0.2756 (5)0.0406 (16)0.440 (6)
H6'0.44910.62800.26990.049*0.440 (6)
C7'0.3566 (2)0.4738 (2)0.4612 (4)0.052 (2)0.440 (6)
H7'10.34220.44820.39970.078*0.440 (6)
H7'20.31880.49830.49000.078*0.440 (6)
H7'30.37400.44370.51490.078*0.440 (6)
C8'0.5110 (2)0.5810 (2)0.1653 (4)0.039 (2)0.440 (6)
C9'0.5606 (2)0.5320 (2)0.1517 (4)0.0379 (19)0.440 (6)
H9'0.57220.50390.20860.046*0.440 (6)
C10'0.5928 (2)0.5251 (2)0.0530 (4)0.045 (2)0.440 (6)
C11'0.5754 (2)0.5671 (2)0.0321 (4)0.052 (3)0.440 (6)
H11'0.59690.56250.09810.063*0.440 (6)
C12'0.5258 (2)0.6161 (2)0.0185 (4)0.058 (3)0.440 (6)
H12'0.51410.64430.07550.070*0.440 (6)
C13'0.4936 (2)0.6231 (2)0.0802 (4)0.049 (2)0.440 (6)
H13'0.46040.65580.08920.059*0.440 (6)
Cl1'0.6585 (5)0.4711 (6)0.0291 (8)0.0866 (18)0.440 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.087 (9)0.075 (7)0.028 (5)0.022 (6)0.006 (5)0.025 (4)
N10.080 (9)0.053 (7)0.033 (5)0.002 (5)0.007 (5)0.011 (5)
C10.067 (6)0.060 (8)0.033 (4)0.015 (5)0.006 (3)0.010 (4)
C20.046 (4)0.032 (7)0.032 (3)0.008 (4)0.004 (3)0.003 (3)
C30.059 (5)0.032 (7)0.042 (4)0.010 (5)0.008 (3)0.002 (4)
C40.046 (4)0.034 (7)0.051 (4)0.004 (4)0.002 (3)0.007 (4)
C50.065 (7)0.050 (6)0.052 (6)0.004 (6)0.010 (5)0.012 (4)
C60.058 (4)0.073 (4)0.040 (3)0.009 (3)0.007 (3)0.018 (3)
C70.067 (4)0.044 (4)0.060 (4)0.005 (3)0.015 (3)0.011 (3)
C80.048 (4)0.044 (4)0.035 (3)0.004 (3)0.000 (3)0.010 (3)
C90.019 (3)0.082 (5)0.061 (4)0.000 (3)0.009 (2)0.021 (3)
C100.044 (4)0.090 (7)0.057 (5)0.020 (4)0.015 (4)0.011 (4)
C110.052 (4)0.097 (10)0.050 (6)0.020 (4)0.003 (4)0.017 (5)
C120.050 (4)0.067 (4)0.055 (4)0.022 (3)0.011 (3)0.010 (3)
C130.065 (4)0.038 (4)0.063 (5)0.003 (3)0.019 (4)0.003 (4)
Cl10.073 (2)0.133 (3)0.107 (5)0.0165 (18)0.030 (3)0.023 (3)
O1'0.051 (8)0.104 (13)0.061 (11)0.032 (8)0.006 (7)0.015 (8)
N1'0.034 (6)0.074 (11)0.041 (8)0.008 (6)0.017 (5)0.014 (7)
C1'0.060 (7)0.062 (11)0.039 (5)0.023 (7)0.007 (4)0.006 (5)
C2'0.054 (6)0.026 (8)0.036 (4)0.009 (6)0.001 (4)0.002 (4)
C3'0.041 (4)0.027 (8)0.038 (4)0.014 (4)0.008 (3)0.007 (4)
C4'0.049 (5)0.021 (7)0.049 (5)0.011 (4)0.003 (4)0.003 (5)
C5'0.049 (5)0.054 (10)0.043 (5)0.003 (6)0.006 (4)0.013 (5)
C6'0.040 (3)0.045 (4)0.037 (3)0.016 (3)0.000 (3)0.005 (3)
C7'0.040 (4)0.057 (5)0.058 (5)0.005 (3)0.004 (3)0.017 (4)
C8'0.045 (4)0.030 (5)0.041 (4)0.012 (3)0.005 (3)0.003 (3)
C9'0.016 (4)0.062 (5)0.035 (4)0.011 (3)0.009 (3)0.009 (3)
C10'0.042 (5)0.065 (6)0.030 (4)0.003 (4)0.010 (4)0.023 (3)
C11'0.053 (5)0.065 (8)0.040 (6)0.015 (4)0.011 (4)0.015 (5)
C12'0.048 (5)0.076 (6)0.051 (5)0.015 (4)0.023 (4)0.007 (4)
C13'0.063 (5)0.049 (5)0.035 (4)0.002 (4)0.016 (3)0.010 (3)
Cl1'0.065 (3)0.099 (3)0.096 (5)0.0217 (19)0.016 (3)0.007 (3)
Geometric parameters (Å, º) top
O1—N11.396 (7)O1'—N1'1.400 (7)
O1—H10.8200O1'—H1'0.8200
N1—C21.292 (8)N1'—C2'1.290 (9)
C1—C21.497 (7)C1'—C2'1.496 (8)
C1—C61.520 (12)C1'—C6'1.520 (13)
C1—H1A0.9700C1'—H1'10.9700
C1—H1B0.9700C1'—H1'20.9700
C2—C31.448 (7)C2'—C3'1.449 (8)
C3—C41.324 (7)C3'—C4'1.324 (8)
C3—H30.9300C3'—H3'0.9300
C4—C71.524 (6)C4'—C7'1.525 (7)
C4—C51.532 (10)C4'—C5'1.533 (10)
C5—C61.456 (10)C5'—C6'1.454 (10)
C5—H5A0.9700C5'—H5'10.9700
C5—H5B0.9700C5'—H5'20.9700
C6—C81.535 (6)C6'—C8'1.525 (6)
C6—H60.9800C6'—H6'0.9800
C7—H7A0.9600C7'—H7'10.9600
C7—H7B0.9600C7'—H7'20.9600
C7—H7C0.9600C7'—H7'30.9600
C8—C91.3900C8'—C13'1.3900
C8—C131.3900C8'—C9'1.3900
C9—C101.3900C9'—C10'1.3900
C9—H90.9300C9'—H9'0.9300
C10—C111.3900C10'—C11'1.3900
C10—Cl11.687 (5)C10'—Cl1'1.710 (6)
C11—C121.3900C11'—C12'1.3900
C11—H110.9300C11'—H11'0.9300
C12—C131.3900C12'—C13'1.3900
C12—H120.9300C12'—H12'0.9300
C13—H130.9300C13'—H13'0.9300
N1—O1—H1109.5N1'—O1'—H1'109.5
C2—N1—O1108.8 (13)C2'—N1'—O1'118.0 (16)
C2—C1—C6112.9 (9)C2'—C1'—C6'113.0 (10)
C2—C1—H1A109.0C2'—C1'—H1'1109.0
C6—C1—H1A109.0C6'—C1'—H1'1109.0
C2—C1—H1B109.0C2'—C1'—H1'2109.0
C6—C1—H1B109.0C6'—C1'—H1'2109.0
H1A—C1—H1B107.8H1'1—C1'—H1'2107.8
N1—C2—C3115.9 (11)N1'—C2'—C3'118.6 (13)
N1—C2—C1126.9 (11)N1'—C2'—C1'120.7 (13)
C3—C2—C1117.1 (7)C3'—C2'—C1'120.0 (9)
C4—C3—C2123.5 (9)C4'—C3'—C2'123.1 (10)
C4—C3—H3118.2C4'—C3'—H3'118.5
C2—C3—H3118.2C2'—C3'—H3'118.5
C3—C4—C7124.2 (11)C3'—C4'—C7'121.2 (13)
C3—C4—C5123.7 (9)C3'—C4'—C5'114.8 (10)
C7—C4—C5111.8 (7)C7'—C4'—C5'123.4 (10)
C6—C5—C4111.8 (9)C6'—C5'—C4'123.9 (11)
C6—C5—H5A109.3C6'—C5'—H5'1106.4
C4—C5—H5A109.3C4'—C5'—H5'1106.4
C6—C5—H5B109.3C6'—C5'—H5'2106.4
C4—C5—H5B109.3C4'—C5'—H5'2106.4
H5A—C5—H5B107.9H5'1—C5'—H5'2106.4
C5—C6—C1121.1 (10)C5'—C6'—C1'109.9 (12)
C5—C6—C8113.3 (8)C5'—C6'—C8'117.3 (9)
C1—C6—C8110.5 (7)C1'—C6'—C8'113.4 (7)
C5—C6—H6103.2C5'—C6'—H6'105.0
C1—C6—H6103.2C1'—C6'—H6'105.0
C8—C6—H6103.2C8'—C6'—H6'105.0
C4—C7—H7A109.5C4'—C7'—H7'1109.5
C4—C7—H7B109.5C4'—C7'—H7'2109.5
H7A—C7—H7B109.5H7'1—C7'—H7'2109.5
C4—C7—H7C109.5C4'—C7'—H7'3109.5
H7A—C7—H7C109.5H7'1—C7'—H7'3109.5
H7B—C7—H7C109.5H7'2—C7'—H7'3109.5
C9—C8—C13120.0C13'—C8'—C9'120.0
C9—C8—C6122.9 (4)C13'—C8'—C6'121.7 (3)
C13—C8—C6117.1 (4)C9'—C8'—C6'118.3 (3)
C8—C9—C10120.0C10'—C9'—C8'120.0
C8—C9—H9120.0C10'—C9'—H9'120.0
C10—C9—H9120.0C8'—C9'—H9'120.0
C9—C10—C11120.0C11'—C10'—C9'120.0
C9—C10—Cl1115.3 (3)C11'—C10'—Cl1'115.5 (4)
C11—C10—Cl1124.6 (3)C9'—C10'—Cl1'124.4 (4)
C12—C11—C10120.0C10'—C11'—C12'120.0
C12—C11—H11120.0C10'—C11'—H11'120.0
C10—C11—H11120.0C12'—C11'—H11'120.0
C11—C12—C13120.0C13'—C12'—C11'120.0
C11—C12—H12120.0C13'—C12'—H12'120.0
C13—C12—H12120.0C11'—C12'—H12'120.0
C12—C13—C8120.0C12'—C13'—C8'120.0
C12—C13—H13120.0C12'—C13'—H13'120.0
C8—C13—H13120.0C8'—C13'—H13'120.0
O1—N1—C2—C3177.7 (17)O1'—N1'—C2'—C3'177 (2)
O1—N1—C2—C17 (3)O1'—N1'—C2'—C1'13 (4)
C6—C1—C2—N1149 (2)C6'—C1'—C2'—N1'140 (2)
C6—C1—C2—C327 (2)C6'—C1'—C2'—C3'30 (3)
N1—C2—C3—C4171.4 (18)N1'—C2'—C3'—C4'172 (2)
C1—C2—C3—C45 (3)C1'—C2'—C3'—C4'2 (3)
C2—C3—C4—C7176.5 (15)C2'—C3'—C4'—C7'171.5 (18)
C2—C3—C4—C510 (3)C2'—C3'—C4'—C5'16 (3)
C3—C4—C5—C60 (3)C3'—C4'—C5'—C6'2 (4)
C7—C4—C5—C6174.3 (14)C7'—C4'—C5'—C6'170.0 (19)
C4—C5—C6—C125 (3)C4'—C5'—C6'—C1'32 (3)
C4—C5—C6—C8159.4 (14)C4'—C5'—C6'—C8'163 (2)
C2—C1—C6—C538 (2)C2'—C1'—C6'—C5'43 (2)
C2—C1—C6—C8174.1 (12)C2'—C1'—C6'—C8'176.8 (15)
C5—C6—C8—C9108.1 (13)C5'—C6'—C8'—C13'111.6 (16)
C1—C6—C8—C9112.4 (10)C1'—C6'—C8'—C13'118.5 (12)
C5—C6—C8—C1371.8 (13)C5'—C6'—C8'—C9'70.0 (16)
C1—C6—C8—C1367.7 (10)C1'—C6'—C8'—C9'59.9 (12)
C13—C8—C9—C100.0C13'—C8'—C9'—C10'0.0
C6—C8—C9—C10179.9 (3)C6'—C8'—C9'—C10'178.4 (4)
C8—C9—C10—C110.0C8'—C9'—C10'—C11'0.0
C8—C9—C10—Cl1177.8 (5)C8'—C9'—C10'—Cl1'175.1 (6)
C9—C10—C11—C120.0C9'—C10'—C11'—C12'0.0
Cl1—C10—C11—C12177.6 (6)Cl1'—C10'—C11'—C12'175.5 (6)
C10—C11—C12—C130.0C10'—C11'—C12'—C13'0.0
C11—C12—C13—C80.0C11'—C12'—C13'—C8'0.0
C9—C8—C13—C120.0C9'—C8'—C13'—C12'0.0
C6—C8—C13—C12179.9 (3)C6'—C8'—C13'—C12'178.4 (4)

Experimental details

Crystal data
Chemical formulaC13H14ClNO
Mr235.70
Crystal system, space groupTetragonal, I41/a
Temperature (K)295
a, c (Å)19.7898 (8), 12.4416 (11)
V3)4872.6 (5)
Z16
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.25 × 0.22 × 0.19
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.930, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
19841, 2394, 1765
Rint0.034
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.242, 1.05
No. of reflections2394
No. of parameters255
No. of restraints93
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.1164P)2 + 10.7128P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.72, 0.50

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Acknowledgements

The authors thank Dr Babu Varghese and the SAIF, IIT, Chennai, India, for the data collection.

References

First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChaudhuri, P. (2003). Coord. Chem. Rev. 243, 143–168.  Web of Science CrossRef CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationKukushkin, V. Yu., Tudela, D. & Pombeiro, A. J. L. (1996). Coord. Chem. Rev. 156, 333–362.  CrossRef CAS Web of Science
First citationRavichandran, K., Ramesh, P., Rani, M., Kabilan, S. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o1506.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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