N-[(1E)-5-(3-Chloro-phen-yl)-3-methyl-cyclo-hex-2-en-1-yl-idene]hydroxyl-amine.

The whole of the title mol-ecule, 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 = 235.70

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 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 ▶); 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004698/nk2191sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004698/nk2191Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H14ClNO	Dx = 1.285 Mg m−3
Mr = 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

Bruker APEXII CCD area-detector diffractometer	2394 independent reflections
Radiation source: fine-focus sealed tube	1765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.930, Tmax = 0.946	k = −24→24
19841 measured reflections	l = −15→15

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(Fo2) + (0.1164P)2 + 10.7128P] where P = (Fo2 + 2Fc2)/3
2394 reflections	(Δ/σ)max = 0.026
255 parameters	Δρmax = 0.72 e Å−3
93 restraints	Δρmin = −0.50 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)