3-Bromo-2-eth­oxy-2-phenyl­cyclo­hexan-1-one oxime

In the title compound, C₁₄H₁₈BrNO₂, the six-membered cyclo­hexa­none ring has a sightly distorted chair conformation. The oximino function in the compound assumes an E configuration, with the hydroxyl group anti to the substitutents on the tertiary C atom. Of the other three substituents, the bromo and eth­oxy groups are axial and the phenyl group is equatorial. Inversion-related mol­ecules form O—H...N hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.034
• wR factor = 0.086
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.86 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.920
            Tmax scaled      0.622 Tmin scaled      0.548
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

3-Bromo-2-ethoxy-2-phenylcyclohexan-1-one oxime

Crystal data

C14H18BrNO2	F(000) = 1280
Mr = 312.20	Dx = 1.411 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 25.650 (11) Å	θ = 9.9–14.2°
b = 7.541 (6) Å	µ = 2.79 mm^−1
c = 15.797 (9) Å	T = 293 K
β = 105.86 (9)°	Block, colourless
V = 2939 (3) Å^3	0.22 × 0.19 × 0.17 mm
Z = 8

Data collection

Nonius MACH3 sealed tube diffractometer	1442 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
ω/2θ scans	h = 0→30
Absorption correction: ψ scan (North et al., 1968)	k = −1→8
Tmin = 0.596, Tmax = 0.676	l = −18→18
3070 measured reflections	3 standard reflections every 60 min
2580 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0322P)^2 + 2.1975P] where P = (Fo^2 + 2Fc^2)/3
2580 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.86280 (13)	0.7658 (4)	0.5645 (2)	0.0402 (8)
N1	0.81149 (11)	0.7540 (4)	0.53651 (17)	0.0462 (7)
O1	0.79439 (9)	0.6408 (3)	0.46354 (15)	0.0623 (7)
H1	0.7613	0.6446	0.4449	0.093*
C2	0.88645 (12)	0.8664 (4)	0.64950 (19)	0.0400 (8)
O2	0.91318 (8)	0.7380 (3)	0.71435 (13)	0.0465 (6)
C22	0.88111 (15)	0.5898 (5)	0.7285 (2)	0.0619 (10)
H22A	0.8683	0.5216	0.6747	0.074*
H22B	0.8500	0.6311	0.7466	0.074*
C23	0.9166 (2)	0.4788 (6)	0.7987 (3)	0.1138 (19)
H23A	0.8966	0.3781	0.8099	0.171*
H23B	0.9290	0.5476	0.8515	0.171*
H23C	0.9473	0.4388	0.7800	0.171*
C3	0.93618 (13)	0.9756 (4)	0.6413 (2)	0.0494 (9)
H3	0.9546	1.0227	0.6996	0.059*
Br1	0.913419 (19)	1.17745 (5)	0.56082 (3)	0.0839 (2)
C4	0.97656 (13)	0.8675 (5)	0.6096 (2)	0.0595 (10)
H4B	0.9924	0.7785	0.6535	0.071*
H4C	1.0055	0.9443	0.6030	0.071*
C5	0.95088 (15)	0.7767 (5)	0.5227 (3)	0.0625 (11)
H5B	0.9775	0.7005	0.5076	0.075*
H5C	0.9398	0.8656	0.4769	0.075*
C6	0.90184 (13)	0.6666 (5)	0.5264 (2)	0.0550 (9)
H6B	0.8831	0.6281	0.4673	0.066*
H6C	0.9141	0.5615	0.5616	0.066*
C7	0.84729 (12)	0.9801 (4)	0.6843 (2)	0.0441 (8)
C8	0.85336 (14)	0.9844 (5)	0.7744 (2)	0.0554 (10)
H8	0.8798	0.9147	0.8117	0.066*
C9	0.82073 (17)	1.0903 (6)	0.8091 (3)	0.0717 (12)
H9	0.8254	1.0913	0.8696	0.086*
C10	0.78147 (17)	1.1944 (6)	0.7560 (3)	0.0813 (13)
H10	0.7592	1.2645	0.7798	0.098*
C11	0.77551 (16)	1.1935 (6)	0.6669 (3)	0.0740 (12)
H11	0.7493	1.2651	0.6303	0.089*
C12	0.80809 (14)	1.0872 (5)	0.6307 (2)	0.0568 (10)
H12	0.8035	1.0880	0.5702	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.039 (2)	0.0411 (18)	0.0418 (19)	−0.0041 (16)	0.0133 (16)	0.0028 (15)
N1	0.0483 (19)	0.0535 (17)	0.0363 (16)	−0.0120 (14)	0.0106 (13)	−0.0057 (14)
O1	0.0553 (15)	0.0808 (19)	0.0500 (15)	−0.0186 (15)	0.0128 (13)	−0.0201 (14)
C2	0.0384 (18)	0.0394 (19)	0.040 (2)	−0.0055 (15)	0.0075 (16)	0.0025 (15)
O2	0.0490 (14)	0.0414 (12)	0.0474 (14)	−0.0068 (11)	0.0101 (11)	0.0096 (11)
C22	0.072 (3)	0.055 (2)	0.061 (2)	−0.018 (2)	0.023 (2)	0.006 (2)
C23	0.129 (4)	0.093 (4)	0.099 (4)	−0.039 (3)	−0.004 (3)	0.054 (3)
C3	0.045 (2)	0.049 (2)	0.054 (2)	−0.0079 (17)	0.0128 (17)	0.0083 (17)
Br1	0.0924 (3)	0.0515 (2)	0.1187 (4)	0.0029 (2)	0.0473 (3)	0.0307 (3)
C4	0.039 (2)	0.064 (3)	0.079 (3)	−0.0087 (19)	0.021 (2)	0.013 (2)
C5	0.055 (2)	0.069 (3)	0.070 (3)	0.005 (2)	0.030 (2)	0.005 (2)
C6	0.056 (2)	0.057 (2)	0.054 (2)	0.000 (2)	0.0188 (18)	−0.0022 (19)
C7	0.0368 (19)	0.0444 (19)	0.051 (2)	−0.0078 (17)	0.0119 (17)	−0.0102 (17)
C8	0.052 (2)	0.058 (2)	0.057 (3)	−0.0115 (19)	0.0157 (19)	−0.0141 (19)
C9	0.067 (3)	0.084 (3)	0.066 (3)	−0.013 (3)	0.022 (2)	−0.030 (2)
C10	0.062 (3)	0.085 (3)	0.101 (4)	−0.001 (3)	0.029 (3)	−0.042 (3)
C11	0.055 (3)	0.070 (3)	0.088 (3)	0.011 (2)	0.007 (2)	−0.020 (3)
C12	0.048 (2)	0.056 (2)	0.065 (2)	0.003 (2)	0.012 (2)	−0.008 (2)

Geometric parameters (Å, º)

C1—N1	1.272 (4)	C4—H4B	0.9700
C1—C6	1.501 (4)	C4—H4C	0.9700
C1—C2	1.517 (4)	C5—C6	1.521 (5)
N1—O1	1.405 (3)	C5—H5B	0.9700
O1—H1	0.8200	C5—H5C	0.9700
C2—O2	1.440 (4)	C6—H6B	0.9700
C2—C7	1.532 (4)	C6—H6C	0.9700
C2—C3	1.553 (4)	C7—C12	1.383 (4)
O2—C22	1.441 (4)	C7—C8	1.390 (4)
C22—C23	1.486 (5)	C8—C9	1.375 (5)
C22—H22A	0.9700	C8—H8	0.9300
C22—H22B	0.9700	C9—C10	1.368 (6)
C23—H23A	0.9600	C9—H9	0.9300
C23—H23B	0.9600	C10—C11	1.375 (6)
C23—H23C	0.9600	C10—H10	0.9300
C3—C4	1.507 (5)	C11—C12	1.389 (5)
C3—Br1	1.966 (3)	C11—H11	0.9300
C3—H3	0.9800	C12—H12	0.9300
C4—C5	1.515 (5)
N1—C1—C6	124.5 (3)	C3—C4—H4C	109.2
N1—C1—C2	117.9 (3)	C5—C4—H4C	109.2
C6—C1—C2	117.1 (3)	H4B—C4—H4C	107.9
C1—N1—O1	112.9 (3)	C4—C5—C6	111.8 (3)
N1—O1—H1	109.5	C4—C5—H5B	109.3
O2—C2—C1	106.9 (3)	C6—C5—H5B	109.3
O2—C2—C7	110.7 (2)	C4—C5—H5C	109.3
C1—C2—C7	117.0 (3)	C6—C5—H5C	109.3
O2—C2—C3	100.0 (2)	H5B—C5—H5C	107.9
C1—C2—C3	109.3 (3)	C1—C6—C5	113.1 (3)
C7—C2—C3	111.5 (3)	C1—C6—H6B	109.0
C2—O2—C22	116.8 (2)	C5—C6—H6B	109.0
O2—C22—C23	107.0 (3)	C1—C6—H6C	109.0
O2—C22—H22A	110.3	C5—C6—H6C	109.0
C23—C22—H22A	110.3	H6B—C6—H6C	107.8
O2—C22—H22B	110.3	C12—C7—C8	118.2 (3)
C23—C22—H22B	110.3	C12—C7—C2	123.0 (3)
H22A—C22—H22B	108.6	C8—C7—C2	118.6 (3)
C22—C23—H23A	109.5	C9—C8—C7	120.8 (4)
C22—C23—H23B	109.5	C9—C8—H8	119.6
H23A—C23—H23B	109.5	C7—C8—H8	119.6
C22—C23—H23C	109.5	C10—C9—C8	121.0 (4)
H23A—C23—H23C	109.5	C10—C9—H9	119.5
H23B—C23—H23C	109.5	C8—C9—H9	119.5
C4—C3—C2	113.3 (3)	C9—C10—C11	118.9 (4)
C4—C3—Br1	108.3 (2)	C9—C10—H10	120.6
C2—C3—Br1	111.0 (2)	C11—C10—H10	120.6
C4—C3—H3	108.0	C10—C11—C12	120.9 (4)
C2—C3—H3	108.0	C10—C11—H11	119.5
Br1—C3—H3	108.0	C12—C11—H11	119.5
C3—C4—C5	112.2 (3)	C7—C12—C11	120.2 (4)
C3—C4—H4B	109.2	C7—C12—H12	119.9
C5—C4—H4B	109.2	C11—C12—H12	119.9
C6—C1—N1—O1	−1.7 (4)	Br1—C3—C4—C5	−67.7 (3)
C2—C1—N1—O1	−172.8 (2)	C3—C4—C5—C6	−53.8 (4)
N1—C1—C2—O2	111.5 (3)	N1—C1—C6—C5	141.2 (3)
C6—C1—C2—O2	−60.3 (3)	C2—C1—C6—C5	−47.6 (4)
N1—C1—C2—C7	−13.2 (4)	C4—C5—C6—C1	48.8 (4)
C6—C1—C2—C7	175.0 (3)	O2—C2—C7—C12	−165.8 (3)
N1—C1—C2—C3	−141.1 (3)	C1—C2—C7—C12	−43.1 (4)
C6—C1—C2—C3	47.1 (4)	C3—C2—C7—C12	83.8 (4)
C1—C2—O2—C22	−55.1 (3)	O2—C2—C7—C8	18.1 (4)
C7—C2—O2—C22	73.4 (3)	C1—C2—C7—C8	140.9 (3)
C3—C2—O2—C22	−168.9 (3)	C3—C2—C7—C8	−92.3 (3)
C2—O2—C22—C23	−178.9 (3)	C12—C7—C8—C9	0.9 (5)
O2—C2—C3—C4	61.4 (3)	C2—C7—C8—C9	177.2 (3)
C1—C2—C3—C4	−50.6 (4)	C7—C8—C9—C10	0.0 (6)
C7—C2—C3—C4	178.4 (3)	C8—C9—C10—C11	−0.9 (6)
O2—C2—C3—Br1	−176.51 (19)	C9—C10—C11—C12	0.9 (6)
C1—C2—C3—Br1	71.5 (3)	C8—C7—C12—C11	−0.9 (5)
C7—C2—C3—Br1	−59.5 (3)	C2—C7—C12—C11	−177.0 (3)
C2—C3—C4—C5	55.9 (4)	C10—C11—C12—C7	−0.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	0.82	2.11	2.829 (4)	146
C6—H6C···Br1^ii	0.97	2.90	3.729 (5)	145

Symmetry codes: (i) −x+3/2, −y+3/2, −z+1; (ii) x, y−1, z.