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

Ganesh, G.; Murugavel, K.; Kannan, P.S.; Amirthaganesan, S.; SubbiahPandi, A.

doi:10.1107/S1600536813004698

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o449

doi:10.1107/S1600536813004698

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

G. Ganesh,^a K. Murugavel,^b P. S. Kannan,^a S. Amirthaganesan ^b and A. SubbiahPandi ^c ^*

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

Experimental

Crystal data

C₁₃H₁₄ClNO
M_r = 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 ) T_min = 0.930, T_max = 0.946
19841 measured reflections
2394 independent reflections
1765 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004698/nk2191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004698/nk2191Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004698/nk2191Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the major component of title compound with 30% probability displacement ellipsoids.
	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

C₁₃H₁₄ClNO	D_x = 1.285 Mg m⁻³
M_r = 235.70	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 2394 reflections
Hall symbol: -I 4ad	θ = 1.5–26.0°
a = 19.7898 (8) Å	µ = 0.29 mm⁻¹
c = 12.4416 (11) Å	T = 295 K
V = 4872.6 (5) Å³	Block, white
Z = 16	0.25 × 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 tube	1765 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.930, T_max = 0.946	k = −24→24
19841 measured reflections	l = −15→15

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.242	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1164P)² + 10.7128P] where P = (F_o² + 2F_c²)/3
2394 reflections	(Δ/σ)_max = 0.026
255 parameters	Δρ_max = 0.72 e Å⁻³
93 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₃H₁₄ClNO	Z = 16
M_r = 235.70	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.29 mm⁻¹
a = 19.7898 (8) Å	T = 295 K
c = 12.4416 (11) Å	0.25 × 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)
T_min = 0.930, T_max = 0.946	R_int = 0.034
19841 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	93 restraints
wR(F²) = 0.242	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1164P)² + 10.7128P] where P = (F_o² + 2F_c²)/3
2394 reflections	Δρ_max = 0.72 e Å⁻³
255 parameters	Δρ_min = −0.50 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5714 (9)	0.6964 (10)	0.5126 (13)	0.064 (4)	0.560 (6)
H1	0.5873	0.7176	0.5632	0.095*	0.560 (6)
N1	0.5172 (8)	0.6572 (8)	0.5484 (11)	0.055 (4)	0.560 (6)
C1	0.5202 (8)	0.6216 (9)	0.3560 (9)	0.053 (4)	0.560 (6)
H1A	0.5687	0.6283	0.3589	0.064*	0.560 (6)
H1B	0.5010	0.6582	0.3141	0.064*	0.560 (6)
C2	0.4922 (8)	0.6246 (8)	0.4677 (7)	0.036 (3)	0.560 (6)
C3	0.4336 (8)	0.5833 (7)	0.4904 (12)	0.044 (4)	0.560 (6)
H3	0.4135	0.5871	0.5577	0.053*	0.560 (6)
C4	0.4070 (6)	0.5404 (6)	0.4205 (13)	0.043 (3)	0.560 (6)
C5	0.4409 (10)	0.5208 (11)	0.3142 (15)	0.055 (5)	0.560 (6)
H5A	0.4480	0.4723	0.3128	0.067*	0.560 (6)
H5B	0.4111	0.5323	0.2550	0.067*	0.560 (6)
C6	0.5054 (4)	0.5550 (4)	0.2999 (5)	0.0570 (18)	0.560 (6)
H6	0.5377	0.5238	0.3331	0.068*	0.560 (6)
C7	0.34307 (17)	0.49939 (17)	0.4407 (3)	0.057 (2)	0.560 (6)
H7A	0.3338	0.4715	0.3793	0.085*	0.560 (6)
H7B	0.3058	0.5295	0.4527	0.085*	0.560 (6)
H7C	0.3494	0.4713	0.5028	0.085*	0.560 (6)
C8	0.52861 (17)	0.55769 (17)	0.1822 (3)	0.0421 (17)	0.560 (6)
C9	0.58200 (17)	0.51926 (17)	0.1431 (3)	0.0541 (19)	0.560 (6)
H9	0.6054	0.4904	0.1888	0.065*	0.560 (6)
C10	0.60045 (17)	0.52400 (17)	0.0355 (3)	0.063 (3)	0.560 (6)
C11	0.56550 (17)	0.56717 (17)	−0.0328 (3)	0.066 (3)	0.560 (6)
H11	0.5778	0.5703	−0.1048	0.080*	0.560 (6)
C12	0.51211 (17)	0.60561 (17)	0.0063 (3)	0.057 (2)	0.560 (6)
H12	0.4887	0.6345	−0.0395	0.069*	0.560 (6)
C13	0.49367 (17)	0.60087 (17)	0.1138 (3)	0.055 (2)	0.560 (6)
H13	0.4580	0.6266	0.1400	0.066*	0.560 (6)
Cl1	0.6641 (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'	0.5786	0.7190	0.5682	0.108*	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)
H1'1	0.5638	0.5713	0.3650	0.064*	0.440 (6)
H1'2	0.5491	0.6484	0.3485	0.064*	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'	0.4183	0.5704	0.5647	0.043*	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)
H5'1	0.4548	0.4921	0.2880	0.059*	0.440 (6)
H5'2	0.3926	0.5384	0.2689	0.059*	0.440 (6)
C6'	0.4783 (3)	0.5882 (4)	0.2756 (5)	0.0406 (16)	0.440 (6)
H6'	0.4491	0.6280	0.2699	0.049*	0.440 (6)
C7'	0.3566 (2)	0.4738 (2)	0.4612 (4)	0.052 (2)	0.440 (6)
H7'1	0.3422	0.4482	0.3997	0.078*	0.440 (6)
H7'2	0.3188	0.4983	0.4900	0.078*	0.440 (6)
H7'3	0.3740	0.4437	0.5149	0.078*	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'	0.5722	0.5039	0.2086	0.046*	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'	0.5969	0.5625	−0.0981	0.063*	0.440 (6)
C12'	0.5258 (2)	0.6161 (2)	−0.0185 (4)	0.058 (3)	0.440 (6)
H12'	0.5141	0.6443	−0.0755	0.070*	0.440 (6)
C13'	0.4936 (2)	0.6231 (2)	0.0802 (4)	0.049 (2)	0.440 (6)
H13'	0.4604	0.6558	0.0892	0.059*	0.440 (6)
Cl1'	0.6585 (5)	0.4711 (6)	0.0291 (8)	0.0866 (18)	0.440 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.087 (9)	0.075 (7)	0.028 (5)	−0.022 (6)	0.006 (5)	−0.025 (4)
N1	0.080 (9)	0.053 (7)	0.033 (5)	0.002 (5)	−0.007 (5)	−0.011 (5)
C1	0.067 (6)	0.060 (8)	0.033 (4)	−0.015 (5)	0.006 (3)	−0.010 (4)
C2	0.046 (4)	0.032 (7)	0.032 (3)	0.008 (4)	0.004 (3)	−0.003 (3)
C3	0.059 (5)	0.032 (7)	0.042 (4)	0.010 (5)	0.008 (3)	0.002 (4)
C4	0.046 (4)	0.034 (7)	0.051 (4)	0.004 (4)	0.002 (3)	0.007 (4)
C5	0.065 (7)	0.050 (6)	0.052 (6)	−0.004 (6)	0.010 (5)	−0.012 (4)
C6	0.058 (4)	0.073 (4)	0.040 (3)	−0.009 (3)	0.007 (3)	−0.018 (3)
C7	0.067 (4)	0.044 (4)	0.060 (4)	−0.005 (3)	0.015 (3)	0.011 (3)
C8	0.048 (4)	0.044 (4)	0.035 (3)	−0.004 (3)	0.000 (3)	−0.010 (3)
C9	0.019 (3)	0.082 (5)	0.061 (4)	0.000 (3)	0.009 (2)	−0.021 (3)
C10	0.044 (4)	0.090 (7)	0.057 (5)	−0.020 (4)	0.015 (4)	−0.011 (4)
C11	0.052 (4)	0.097 (10)	0.050 (6)	−0.020 (4)	0.003 (4)	−0.017 (5)
C12	0.050 (4)	0.067 (4)	0.055 (4)	−0.022 (3)	0.011 (3)	0.010 (3)
C13	0.065 (4)	0.038 (4)	0.063 (5)	−0.003 (3)	0.019 (4)	0.003 (4)
Cl1	0.073 (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—N1	1.396 (7)	O1'—N1'	1.400 (7)
O1—H1	0.8200	O1'—H1'	0.8200
N1—C2	1.292 (8)	N1'—C2'	1.290 (9)
C1—C2	1.497 (7)	C1'—C2'	1.496 (8)
C1—C6	1.520 (12)	C1'—C6'	1.520 (13)
C1—H1A	0.9700	C1'—H1'1	0.9700
C1—H1B	0.9700	C1'—H1'2	0.9700
C2—C3	1.448 (7)	C2'—C3'	1.449 (8)
C3—C4	1.324 (7)	C3'—C4'	1.324 (8)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C7	1.524 (6)	C4'—C7'	1.525 (7)
C4—C5	1.532 (10)	C4'—C5'	1.533 (10)
C5—C6	1.456 (10)	C5'—C6'	1.454 (10)
C5—H5A	0.9700	C5'—H5'1	0.9700
C5—H5B	0.9700	C5'—H5'2	0.9700
C6—C8	1.535 (6)	C6'—C8'	1.525 (6)
C6—H6	0.9800	C6'—H6'	0.9800
C7—H7A	0.9600	C7'—H7'1	0.9600
C7—H7B	0.9600	C7'—H7'2	0.9600
C7—H7C	0.9600	C7'—H7'3	0.9600
C8—C9	1.3900	C8'—C13'	1.3900
C8—C13	1.3900	C8'—C9'	1.3900
C9—C10	1.3900	C9'—C10'	1.3900
C9—H9	0.9300	C9'—H9'	0.9300
C10—C11	1.3900	C10'—C11'	1.3900
C10—Cl1	1.687 (5)	C10'—Cl1'	1.710 (6)
C11—C12	1.3900	C11'—C12'	1.3900
C11—H11	0.9300	C11'—H11'	0.9300
C12—C13	1.3900	C12'—C13'	1.3900
C12—H12	0.9300	C12'—H12'	0.9300
C13—H13	0.9300	C13'—H13'	0.9300

N1—O1—H1	109.5	N1'—O1'—H1'	109.5
C2—N1—O1	108.8 (13)	C2'—N1'—O1'	118.0 (16)
C2—C1—C6	112.9 (9)	C2'—C1'—C6'	113.0 (10)
C2—C1—H1A	109.0	C2'—C1'—H1'1	109.0
C6—C1—H1A	109.0	C6'—C1'—H1'1	109.0
C2—C1—H1B	109.0	C2'—C1'—H1'2	109.0
C6—C1—H1B	109.0	C6'—C1'—H1'2	109.0
H1A—C1—H1B	107.8	H1'1—C1'—H1'2	107.8
N1—C2—C3	115.9 (11)	N1'—C2'—C3'	118.6 (13)
N1—C2—C1	126.9 (11)	N1'—C2'—C1'	120.7 (13)
C3—C2—C1	117.1 (7)	C3'—C2'—C1'	120.0 (9)
C4—C3—C2	123.5 (9)	C4'—C3'—C2'	123.1 (10)
C4—C3—H3	118.2	C4'—C3'—H3'	118.5
C2—C3—H3	118.2	C2'—C3'—H3'	118.5
C3—C4—C7	124.2 (11)	C3'—C4'—C7'	121.2 (13)
C3—C4—C5	123.7 (9)	C3'—C4'—C5'	114.8 (10)
C7—C4—C5	111.8 (7)	C7'—C4'—C5'	123.4 (10)
C6—C5—C4	111.8 (9)	C6'—C5'—C4'	123.9 (11)
C6—C5—H5A	109.3	C6'—C5'—H5'1	106.4
C4—C5—H5A	109.3	C4'—C5'—H5'1	106.4
C6—C5—H5B	109.3	C6'—C5'—H5'2	106.4
C4—C5—H5B	109.3	C4'—C5'—H5'2	106.4
H5A—C5—H5B	107.9	H5'1—C5'—H5'2	106.4
C5—C6—C1	121.1 (10)	C5'—C6'—C1'	109.9 (12)
C5—C6—C8	113.3 (8)	C5'—C6'—C8'	117.3 (9)
C1—C6—C8	110.5 (7)	C1'—C6'—C8'	113.4 (7)
C5—C6—H6	103.2	C5'—C6'—H6'	105.0
C1—C6—H6	103.2	C1'—C6'—H6'	105.0
C8—C6—H6	103.2	C8'—C6'—H6'	105.0
C4—C7—H7A	109.5	C4'—C7'—H7'1	109.5
C4—C7—H7B	109.5	C4'—C7'—H7'2	109.5
H7A—C7—H7B	109.5	H7'1—C7'—H7'2	109.5
C4—C7—H7C	109.5	C4'—C7'—H7'3	109.5
H7A—C7—H7C	109.5	H7'1—C7'—H7'3	109.5
H7B—C7—H7C	109.5	H7'2—C7'—H7'3	109.5
C9—C8—C13	120.0	C13'—C8'—C9'	120.0
C9—C8—C6	122.9 (4)	C13'—C8'—C6'	121.7 (3)
C13—C8—C6	117.1 (4)	C9'—C8'—C6'	118.3 (3)
C8—C9—C10	120.0	C10'—C9'—C8'	120.0
C8—C9—H9	120.0	C10'—C9'—H9'	120.0
C10—C9—H9	120.0	C8'—C9'—H9'	120.0
C9—C10—C11	120.0	C11'—C10'—C9'	120.0
C9—C10—Cl1	115.3 (3)	C11'—C10'—Cl1'	115.5 (4)
C11—C10—Cl1	124.6 (3)	C9'—C10'—Cl1'	124.4 (4)
C12—C11—C10	120.0	C10'—C11'—C12'	120.0
C12—C11—H11	120.0	C10'—C11'—H11'	120.0
C10—C11—H11	120.0	C12'—C11'—H11'	120.0
C11—C12—C13	120.0	C13'—C12'—C11'	120.0
C11—C12—H12	120.0	C13'—C12'—H12'	120.0
C13—C12—H12	120.0	C11'—C12'—H12'	120.0
C12—C13—C8	120.0	C12'—C13'—C8'	120.0
C12—C13—H13	120.0	C12'—C13'—H13'	120.0
C8—C13—H13	120.0	C8'—C13'—H13'	120.0

O1—N1—C2—C3	−177.7 (17)	O1'—N1'—C2'—C3'	177 (2)
O1—N1—C2—C1	7 (3)	O1'—N1'—C2'—C1'	−13 (4)
C6—C1—C2—N1	149 (2)	C6'—C1'—C2'—N1'	−140 (2)
C6—C1—C2—C3	−27 (2)	C6'—C1'—C2'—C3'	30 (3)
N1—C2—C3—C4	−171.4 (18)	N1'—C2'—C3'—C4'	172 (2)
C1—C2—C3—C4	5 (3)	C1'—C2'—C3'—C4'	2 (3)
C2—C3—C4—C7	−176.5 (15)	C2'—C3'—C4'—C7'	171.5 (18)
C2—C3—C4—C5	10 (3)	C2'—C3'—C4'—C5'	−16 (3)
C3—C4—C5—C6	0 (3)	C3'—C4'—C5'—C6'	−2 (4)
C7—C4—C5—C6	−174.3 (14)	C7'—C4'—C5'—C6'	170.0 (19)
C4—C5—C6—C1	−25 (3)	C4'—C5'—C6'—C1'	32 (3)
C4—C5—C6—C8	−159.4 (14)	C4'—C5'—C6'—C8'	163 (2)
C2—C1—C6—C5	38 (2)	C2'—C1'—C6'—C5'	−43 (2)
C2—C1—C6—C8	174.1 (12)	C2'—C1'—C6'—C8'	−176.8 (15)
C5—C6—C8—C9	−108.1 (13)	C5'—C6'—C8'—C13'	111.6 (16)
C1—C6—C8—C9	112.4 (10)	C1'—C6'—C8'—C13'	−118.5 (12)
C5—C6—C8—C13	71.8 (13)	C5'—C6'—C8'—C9'	−70.0 (16)
C1—C6—C8—C13	−67.7 (10)	C1'—C6'—C8'—C9'	59.9 (12)
C13—C8—C9—C10	0.0	C13'—C8'—C9'—C10'	0.0
C6—C8—C9—C10	179.9 (3)	C6'—C8'—C9'—C10'	−178.4 (4)
C8—C9—C10—C11	0.0	C8'—C9'—C10'—C11'	0.0
C8—C9—C10—Cl1	−177.8 (5)	C8'—C9'—C10'—Cl1'	175.1 (6)
C9—C10—C11—C12	0.0	C9'—C10'—C11'—C12'	0.0
Cl1—C10—C11—C12	177.6 (6)	Cl1'—C10'—C11'—C12'	−175.5 (6)
C10—C11—C12—C13	0.0	C10'—C11'—C12'—C13'	0.0
C11—C12—C13—C8	0.0	C11'—C12'—C13'—C8'	0.0
C9—C8—C13—C12	0.0	C9'—C8'—C13'—C12'	0.0
C6—C8—C13—C12	−179.9 (3)	C6'—C8'—C13'—C12'	178.4 (4)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄ClNO
M_r	235.70
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	295
a, c (Å)	19.7898 (8), 12.4416 (11)
V (Å³)	4872.6 (5)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.930, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	19841, 2394, 1765
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.242, 1.05
No. of reflections	2394
No. of parameters	255
No. of restraints	93
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1164P)² + 10.7128P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	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

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