3-Cyano-3-methyl-5-phenyl­cyclo­hexa­none

In the title mol­ecule, C₁₄H₁₅NO, the cyclo­hexane ring adopts a chair conformation. The cyano group and the methyl group have axial and equatorial orientations, respectively. The phenyl ring has an equatorial orientation.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.095
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    1.700
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       1.70
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.40
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C311    ..       5.02 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.05
           From the CIF: _reflns_number_total               1755
           Count of symmetry unique reflns         1760
           Completeness (_total/calc)             99.72%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C5     = ...          R

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

   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

3-Cyano-3-methyl-5-phenylcyclohexanone

Crystal data

C14H15NO	Dx = 1.238 Mg m^−3
Mr = 213.27	Melting point: 367 K
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 1875 reflections
a = 11.5745 (3) Å	θ = 2.0–30.0°
b = 17.5499 (5) Å	µ = 0.08 mm^−1
c = 11.2629 (3) Å	T = 160 K
V = 2287.85 (11) Å^3	Needle, colourless
Z = 8	0.35 × 0.33 × 0.28 mm
F(000) = 912

Data collection

Nonius KappaCCD area-detector diffractometer	1527 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	Rint = 0.071
Horizontally mounted graphite crystal monochromator	θmax = 30.1°, θmin = 2.3°
Detector resolution: 9 pixels mm^-1	h = 0→16
φ and ω scans with κ offsets	k = 0→24
24679 measured reflections	l = −15→0
1755 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.403P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.20 e Å^−3
1755 reflections	Δρmin = −0.20 e Å^−3
146 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.025 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs?
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.4 (17)

Special details

Experimental. Solvent used: Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.508 (2) Frames collected: 282 Seconds exposure per frame: 10 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.67269 (11)	0.17288 (8)	0.41296 (13)	0.0322 (4)
N311	0.47108 (15)	0.34794 (9)	0.30130 (16)	0.0341 (5)
C1	0.63695 (14)	0.16634 (10)	0.31227 (16)	0.0219 (5)
C2	0.67655 (13)	0.21855 (9)	0.21340 (17)	0.0242 (5)
C3	0.57317 (13)	0.25636 (9)	0.14918 (15)	0.0211 (4)
C4	0.48687 (15)	0.19449 (9)	0.10941 (16)	0.0215 (4)
C5	0.44500 (13)	0.14522 (9)	0.21264 (15)	0.0191 (4)
C6	0.54868 (14)	0.10771 (9)	0.27681 (16)	0.0223 (4)
C31	0.61459 (16)	0.30263 (10)	0.04172 (17)	0.0281 (5)
C51	0.35650 (13)	0.08587 (9)	0.17547 (16)	0.0200 (4)
C52	0.26593 (15)	0.06824 (9)	0.25170 (16)	0.0246 (5)
C53	0.18407 (15)	0.01318 (10)	0.22119 (19)	0.0282 (5)
C54	0.19277 (15)	−0.02514 (10)	0.11449 (17)	0.0285 (5)
C55	0.28307 (15)	−0.00870 (10)	0.03784 (17)	0.0287 (5)
C56	0.36404 (14)	0.04687 (9)	0.06765 (16)	0.0237 (5)
C311	0.51537 (14)	0.30826 (9)	0.23456 (17)	0.0236 (5)
H2A	0.72717	0.25866	0.24679	0.0290*
H2B	0.72233	0.18890	0.15529	0.0290*
H4A	0.52428	0.16148	0.04939	0.0258*
H4B	0.41947	0.21924	0.07143	0.0258*
H5	0.40649	0.17987	0.27098	0.0229*
H6A	0.58502	0.06976	0.22355	0.0268*
H6B	0.52088	0.08066	0.34846	0.0268*
H31A	0.65252	0.26860	−0.01520	0.0422*
H31B	0.54822	0.32723	0.00364	0.0422*
H31C	0.66950	0.34163	0.06807	0.0422*
H52	0.25963	0.09400	0.32560	0.0296*
H53	0.12228	0.00207	0.27393	0.0339*
H54	0.13710	−0.06262	0.09371	0.0342*
H55	0.28979	−0.03539	−0.03521	0.0344*
H56	0.42499	0.05834	0.01407	0.0284*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0336 (7)	0.0357 (7)	0.0274 (7)	−0.0028 (5)	−0.0102 (6)	0.0013 (6)
N311	0.0409 (9)	0.0275 (8)	0.0339 (9)	0.0038 (7)	0.0051 (8)	−0.0004 (7)
C1	0.0199 (7)	0.0215 (8)	0.0243 (9)	0.0044 (6)	−0.0033 (7)	−0.0007 (6)
C2	0.0200 (7)	0.0247 (8)	0.0278 (9)	−0.0001 (6)	−0.0007 (7)	0.0002 (7)
C3	0.0228 (7)	0.0205 (7)	0.0201 (8)	−0.0026 (6)	−0.0011 (7)	0.0014 (6)
C4	0.0250 (8)	0.0205 (7)	0.0190 (8)	−0.0046 (6)	−0.0022 (7)	0.0026 (6)
C5	0.0212 (7)	0.0188 (7)	0.0173 (7)	0.0013 (5)	−0.0013 (6)	0.0007 (6)
C6	0.0250 (8)	0.0188 (7)	0.0231 (8)	0.0015 (6)	−0.0030 (7)	0.0012 (7)
C31	0.0331 (9)	0.0291 (8)	0.0222 (8)	−0.0088 (7)	−0.0003 (8)	0.0029 (7)
C51	0.0218 (7)	0.0178 (7)	0.0205 (8)	0.0008 (5)	−0.0029 (6)	0.0034 (6)
C52	0.0271 (9)	0.0236 (7)	0.0232 (8)	−0.0004 (6)	0.0014 (7)	0.0031 (7)
C53	0.0257 (8)	0.0282 (9)	0.0307 (9)	−0.0056 (7)	0.0009 (8)	0.0057 (8)
C54	0.0309 (9)	0.0257 (8)	0.0289 (9)	−0.0080 (7)	−0.0089 (8)	0.0047 (8)
C55	0.0386 (10)	0.0243 (8)	0.0232 (8)	−0.0053 (7)	−0.0066 (8)	0.0002 (7)
C56	0.0281 (8)	0.0217 (8)	0.0214 (8)	−0.0013 (6)	−0.0018 (7)	0.0000 (7)
C311	0.0258 (8)	0.0194 (7)	0.0256 (9)	−0.0019 (6)	−0.0023 (7)	0.0048 (7)

Geometric parameters (Å, º)

O1—C1	1.213 (2)	C55—C56	1.394 (2)
N311—C311	1.146 (2)	C2—H2A	0.9900
C1—C2	1.513 (2)	C2—H2B	0.9900
C1—C6	1.504 (2)	C4—H4A	0.9900
C2—C3	1.548 (2)	C4—H4B	0.9900
C3—C4	1.542 (2)	C5—H5	1.0000
C3—C31	1.534 (2)	C6—H6A	0.9900
C3—C311	1.484 (2)	C6—H6B	0.9900
C4—C5	1.528 (2)	C31—H31A	0.9800
C5—C6	1.548 (2)	C31—H31B	0.9800
C5—C51	1.520 (2)	C31—H31C	0.9800
C51—C52	1.390 (2)	C52—H52	0.9500
C51—C56	1.397 (2)	C53—H53	0.9500
C52—C53	1.396 (2)	C54—H54	0.9500
C53—C54	1.381 (3)	C55—H55	0.9500
C54—C55	1.386 (3)	C56—H56	0.9500
O1···H31A^i	2.7500	H4A···H31A	2.5000
O1···H54^ii	2.8400	H4A···H56	2.1800
O1···H55^ii	2.8300	H4A···N311^ix	2.8000
O1···H4B^iii	2.8100	H4B···C56	3.0900
O1···H31B^iii	2.7500	H4B···H31B	2.5300
N311···H4A^iii	2.8000	H4B···O1^ix	2.8100
N311···H53^iv	2.9300	H5···C311	2.6100
C6···C311	3.573 (2)	H5···H52	2.3500
C52···C55^v	3.540 (3)	H5···C31^iii	3.0700
C55···C52^vi	3.540 (3)	H5···H2A^viii	2.3500
C56···C56^vii	3.551 (2)	H6A···C51^vii	2.8700
C1···H31B^iii	3.0400	H6A···C52^vii	2.9900
C4···H56	2.7200	H6A···C53^vii	3.0400
C5···H2A^viii	3.0600	H6A···C54^vii	2.9600
C6···H31B^iii	3.0100	H6A···C55^vii	2.8000
C31···H5^ix	3.0700	H6A···C56^vii	2.7600
C51···H31C^viii	2.7900	H6B···H31B^iii	2.5100
C51···H6A^vii	2.8700	H31A···H2B	2.5100
C52···H55^v	3.0800	H31A···H4A	2.5000
C52···H2A^viii	3.0700	H31A···O1^xi	2.7500
C52···H6A^vii	2.9900	H31B···H4B	2.5300
C52···H31C^viii	2.8300	H31B···O1^ix	2.7500
C53···H55^v	2.8900	H31B···C1^ix	3.0400
C53···H31C^viii	3.0800	H31B···C6^ix	3.0100
C53···H6A^vii	3.0400	H31B···H6B^ix	2.5100
C54···H6A^vii	2.9600	H31C···H2A	2.5700
C54···H2B^vii	3.0700	H31C···C51^x	2.7900
C55···H6A^vii	2.8000	H31C···C52^x	2.8300
C55···H52^vi	3.0300	H31C···C53^x	3.0800
C56···H4A	2.7400	H31C···C56^x	2.9800
C56···H4B	3.0900	H52···H5	2.3500
C56···H6A^vii	2.7600	H52···C55^v	3.0300
C56···H31C^viii	2.9800	H53···H55^v	2.4700
C311···C6	3.573 (2)	H53···N311^xii	2.9300
C311···H5	2.6100	H54···O1^xiii	2.8400
H2A···H31C	2.5700	H55···C52^vi	3.0800
H2A···C5^x	3.0600	H55···C53^vi	2.8900
H2A···C52^x	3.0700	H55···H53^vi	2.4700
H2A···H5^x	2.3500	H55···O1^xiii	2.8300
H2B···H31A	2.5100	H56···C4	2.7200
H2B···C54^vii	3.0700	H56···H4A	2.1800
H4A···C56	2.7400
O1—C1—C2	121.84 (16)	C3—C4—H4A	109.00
O1—C1—C6	123.01 (16)	H4A—C4—H4B	108.00
C2—C1—C6	115.13 (15)	C5—C4—H4A	109.00
C1—C2—C3	111.68 (13)	C5—C4—H4B	109.00
C2—C3—C4	109.56 (13)	C51—C5—H5	107.00
C2—C3—C31	110.73 (13)	C4—C5—H5	107.00
C2—C3—C311	107.99 (14)	C6—C5—H5	107.00
C4—C3—C31	110.24 (14)	C1—C6—H6B	109.00
C4—C3—C311	109.18 (13)	C1—C6—H6A	109.00
C31—C3—C311	109.10 (14)	H6A—C6—H6B	108.00
C3—C4—C5	112.52 (14)	C5—C6—H6A	109.00
C4—C5—C6	110.49 (13)	C5—C6—H6B	109.00
C4—C5—C51	113.08 (14)	H31A—C31—H31B	109.00
C6—C5—C51	111.08 (13)	C3—C31—H31A	109.00
C1—C6—C5	111.08 (13)	C3—C31—H31B	109.00
C5—C51—C52	119.39 (15)	C3—C31—H31C	109.00
C5—C51—C56	122.23 (14)	H31A—C31—H31C	109.00
C52—C51—C56	118.37 (15)	H31B—C31—H31C	109.00
C51—C52—C53	120.92 (17)	C51—C52—H52	120.00
C52—C53—C54	120.12 (17)	C53—C52—H52	120.00
C53—C54—C55	119.72 (16)	C54—C53—H53	120.00
C54—C55—C56	120.18 (17)	C52—C53—H53	120.00
C51—C56—C55	120.69 (16)	C55—C54—H54	120.00
C3—C2—H2A	109.00	C53—C54—H54	120.00
C1—C2—H2A	109.00	C54—C55—H55	120.00
C1—C2—H2B	109.00	C56—C55—H55	120.00
C3—C2—H2B	109.00	C55—C56—H56	120.00
H2A—C2—H2B	108.00	C51—C56—H56	120.00
C3—C4—H4B	109.00	N311—C311—C3	179.39 (19)
C1—C2—C3—C4	−52.55 (18)	C51—C5—C6—C1	179.31 (14)
C2—C3—C4—C5	56.44 (18)	C4—C5—C51—C52	−143.33 (15)
C3—C4—C5—C6	−56.90 (17)	C4—C5—C51—C56	38.0 (2)
C4—C5—C6—C1	52.96 (18)	C6—C5—C51—C52	91.77 (18)
C5—C6—C1—C2	−52.09 (19)	C6—C5—C51—C56	−86.90 (19)
C6—C1—C2—C3	52.45 (19)	C5—C51—C52—C53	−179.02 (15)
O1—C1—C2—C3	−126.12 (17)	C56—C51—C52—C53	−0.3 (2)
O1—C1—C6—C5	126.46 (18)	C5—C51—C56—C55	178.24 (15)
C1—C2—C3—C31	−174.35 (14)	C52—C51—C56—C55	−0.4 (2)
C1—C2—C3—C311	66.26 (17)	C51—C52—C53—C54	0.5 (3)
C31—C3—C4—C5	178.54 (13)	C52—C53—C54—C55	0.0 (3)
C311—C3—C4—C5	−61.63 (17)	C53—C54—C55—C56	−0.7 (3)
C3—C4—C5—C51	177.87 (13)	C54—C55—C56—C51	1.0 (3)

Symmetry codes: (i) −x+3/2, y, z+1/2; (ii) x+1/2, −y, z+1/2; (iii) −x+1, −y+1/2, z+1/2; (iv) −x+1/2, y+1/2, z; (v) −x+1/2, y, z+1/2; (vi) −x+1/2, y, z−1/2; (vii) −x+1, −y, z; (viii) x−1/2, −y+1/2, z; (ix) −x+1, −y+1/2, z−1/2; (x) x+1/2, −y+1/2, z; (xi) −x+3/2, y, z−1/2; (xii) −x+1/2, y−1/2, z; (xiii) x−1/2, −y, z−1/2.