3-(4-Hydro­xy­styryl)-1,1-di­methyl­cyclo­hex-3-en-5-one

The crystal structure of the title compound, C₁₆H₁₈O₂, contains one mol­ecule in the asymmetric unit. With the exception of the C(CH₃)₂ group, it is nearly planar. The intermolecular hydrogen bond formed by the hydroxy group with the O-carbonyl atom [O...O = 2.720 Å and O—H...O = 166°] links the mol­ecules into infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.108
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         26 Perc.

Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.132
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13

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

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

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO & SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I)

Crystal data

C16H18O2	F(000) = 520
Mr = 242.30	Dx = 1.182 Mg m^−3
Monoclinic, P21/n	Melting point = 455–456 K
Hall symbol: -p 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.693 (3) Å	Cell parameters from 16335 reflections
b = 6.0684 (12) Å	θ = 1.9–25.0°
c = 15.266 (3) Å	µ = 0.08 mm^−1
β = 90.58 (3)°	T = 291 K
V = 1361.1 (5) Å^3	Needle, yellow
Z = 4	0.38 × 0.06 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer	616 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.132
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −14→17
16335 measured reflections	k = −7→7
2351 independent reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.108	w = exp[8(sinθ/λ)^2)]/σ^2(Fo^2)
S = 0.96	(Δ/σ)max < 0.001
2351 reflections	Δρmax = 0.09 e Å^−3
167 parameters	Δρmin = −0.10 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (14)

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
O1	0.81570 (18)	0.4803 (4)	−0.16313 (16)	0.0781 (8)
H1	0.8299	0.3938	−0.2020	0.117*
O2	0.39124 (17)	−0.7229 (4)	0.21129 (13)	0.0695 (8)
C1	0.7637 (2)	0.3731 (6)	−0.1023 (2)	0.0585 (10)
C2	0.7268 (2)	0.1696 (6)	−0.1185 (2)	0.0611 (10)
H2	0.7353	0.1020	−0.1725	0.073*
C3	0.6768 (2)	0.0647 (5)	−0.0540 (2)	0.0593 (10)
H3	0.6517	−0.0730	−0.0655	0.071*
C4	0.6636 (2)	0.1615 (5)	0.0277 (2)	0.0523 (9)
C5	0.6998 (2)	0.3693 (5)	0.0408 (2)	0.0615 (10)
H5	0.6907	0.4395	0.0941	0.074*
C6	0.7495 (2)	0.4761 (5)	−0.0235 (2)	0.0635 (10)
H6	0.7729	0.6162	−0.0133	0.076*
C7	0.6175 (2)	0.0494 (5)	0.0992 (2)	0.0585 (10)
H7	0.6195	0.1193	0.1534	0.070*
C8	0.5726 (2)	−0.1416 (6)	0.0959 (2)	0.0583 (9)
H8	0.5669	−0.2083	0.0413	0.070*
C9	0.5320 (2)	−0.2551 (5)	0.1693 (2)	0.0538 (9)
C10	0.4823 (2)	−0.4373 (5)	0.1560 (2)	0.0574 (9)
H10	0.4768	−0.4914	0.0992	0.069*
C11	0.4365 (2)	−0.5546 (6)	0.2256 (2)	0.0570 (9)
C12	0.4447 (2)	−0.4606 (5)	0.31584 (19)	0.0638 (10)
H12A	0.4394	−0.5794	0.3580	0.077*
H12B	0.3945	−0.3600	0.3252	0.077*
C13	0.5346 (2)	−0.3371 (5)	0.3333 (2)	0.0624 (10)
C14	0.5456 (2)	−0.1684 (5)	0.26047 (19)	0.0622 (10)
H14A	0.5025	−0.0500	0.2699	0.075*
H14B	0.6062	−0.1059	0.2649	0.075*
C15	0.6143 (3)	−0.5013 (6)	0.3352 (2)	0.0877 (13)
H15A	0.6699	−0.4238	0.3473	0.132*
H15B	0.6183	−0.5734	0.2794	0.132*
H15C	0.6042	−0.6091	0.3801	0.132*
C16	0.5291 (3)	−0.2168 (5)	0.42195 (19)	0.0909 (13)
H16A	0.4769	−0.1218	0.4219	0.136*
H16B	0.5832	−0.1306	0.4310	0.136*
H16C	0.5238	−0.3231	0.4682	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0793 (19)	0.0783 (18)	0.0773 (18)	−0.0031 (16)	0.0338 (15)	0.0062 (14)
O2	0.0753 (19)	0.0712 (17)	0.0624 (15)	−0.0174 (14)	0.0183 (13)	−0.0089 (13)
C1	0.058 (3)	0.059 (2)	0.059 (2)	0.003 (2)	0.017 (2)	0.003 (2)
C2	0.062 (3)	0.073 (3)	0.049 (2)	0.003 (2)	0.0151 (18)	−0.0067 (19)
C3	0.056 (2)	0.067 (3)	0.054 (2)	−0.0030 (19)	0.0092 (19)	−0.0041 (19)
C4	0.053 (2)	0.055 (2)	0.050 (2)	0.0001 (19)	0.0125 (17)	0.0001 (18)
C5	0.067 (3)	0.062 (3)	0.056 (2)	0.000 (2)	0.0151 (19)	−0.0060 (19)
C6	0.066 (3)	0.054 (2)	0.071 (2)	0.0028 (19)	0.015 (2)	−0.007 (2)
C7	0.062 (3)	0.061 (2)	0.052 (2)	0.000 (2)	0.0107 (18)	−0.0019 (18)
C8	0.057 (2)	0.068 (3)	0.050 (2)	−0.002 (2)	0.0098 (18)	−0.0038 (19)
C9	0.054 (2)	0.061 (2)	0.047 (2)	0.0054 (18)	0.0097 (17)	−0.0034 (19)
C10	0.058 (2)	0.067 (3)	0.047 (2)	−0.003 (2)	0.0104 (17)	−0.0038 (18)
C11	0.055 (3)	0.060 (2)	0.056 (2)	0.002 (2)	0.0106 (18)	−0.0047 (19)
C12	0.074 (3)	0.066 (2)	0.052 (2)	−0.003 (2)	0.0130 (18)	−0.0034 (18)
C13	0.072 (3)	0.069 (2)	0.047 (2)	−0.008 (2)	0.0035 (18)	−0.0003 (19)
C14	0.061 (2)	0.069 (2)	0.057 (2)	−0.004 (2)	0.0121 (18)	−0.0025 (19)
C15	0.083 (3)	0.100 (3)	0.081 (3)	0.000 (3)	−0.011 (2)	0.005 (2)
C16	0.122 (4)	0.099 (3)	0.053 (2)	−0.029 (3)	0.011 (2)	−0.014 (2)

Geometric parameters (Å, º)

O1—C1	1.373 (4)	C9—C14	1.499 (4)
O1—H1	0.820	C10—C11	1.450 (4)
O2—C11	1.237 (3)	C10—H10	0.930
C1—C2	1.370 (4)	C11—C12	1.494 (4)
C1—C6	1.373 (4)	C12—C13	1.540 (4)
C2—C3	1.389 (4)	C12—H12A	0.970
C2—H2	0.930	C12—H12B	0.970
C3—C4	1.393 (4)	C13—C14	1.521 (4)
C3—H3	0.930	C13—C15	1.537 (4)
C4—C5	1.383 (4)	C13—C16	1.541 (4)
C4—C7	1.459 (4)	C14—H14A	0.970
C5—C6	1.389 (4)	C14—H14B	0.970
C5—H5	0.930	C15—H15A	0.960
C6—H6	0.930	C15—H15B	0.960
C7—C8	1.334 (4)	C15—H15C	0.960
C7—H7	0.930	C16—H16A	0.960
C8—C9	1.449 (4)	C16—H16B	0.960
C8—H8	0.930	C16—H16C	0.960
C9—C10	1.340 (4)
C1—O1—H1	109.5	O2—C11—C12	121.1 (3)
C2—C1—C6	120.4 (3)	C10—C11—C12	117.0 (3)
C2—C1—O1	121.8 (3)	C11—C12—C13	114.0 (3)
C6—C1—O1	117.9 (3)	C11—C12—H12A	108.8
C1—C2—C3	119.7 (3)	C13—C12—H12A	108.8
C1—C2—H2	120.1	C11—C12—H12B	108.8
C3—C2—H2	120.1	C13—C12—H12B	108.8
C2—C3—C4	121.4 (3)	H12A—C12—H12B	107.6
C2—C3—H3	119.3	C14—C13—C15	111.3 (3)
C4—C3—H3	119.3	C14—C13—C16	109.3 (3)
C5—C4—C3	117.2 (3)	C15—C13—C16	109.7 (3)
C5—C4—C7	119.9 (3)	C14—C13—C12	107.3 (3)
C3—C4—C7	122.9 (3)	C15—C13—C12	109.8 (3)
C4—C5—C6	121.8 (3)	C16—C13—C12	109.3 (3)
C4—C5—H5	119.1	C9—C14—C13	115.4 (3)
C6—C5—H5	119.1	C9—C14—H14A	108.4
C1—C6—C5	119.4 (3)	C13—C14—H14A	108.4
C1—C6—H6	120.3	C9—C14—H14B	108.4
C5—C6—H6	120.3	C13—C14—H14B	108.4
C8—C7—C4	127.6 (3)	H14A—C14—H14B	107.5
C8—C7—H7	116.2	C13—C15—H15A	109.5
C4—C7—H7	116.2	C13—C15—H15B	109.5
C7—C8—C9	126.2 (3)	H15A—C15—H15B	109.5
C7—C8—H8	116.9	C13—C15—H15C	109.5
C9—C8—H8	116.9	H15A—C15—H15C	109.5
C10—C9—C8	120.2 (3)	H15B—C15—H15C	109.5
C10—C9—C14	119.8 (3)	C13—C16—H16A	109.5
C8—C9—C14	119.9 (3)	C13—C16—H16B	109.5
C9—C10—C11	123.4 (3)	H16A—C16—H16B	109.5
C9—C10—H10	118.3	C13—C16—H16C	109.5
C11—C10—H10	118.3	H16A—C16—H16C	109.5
O2—C11—C10	121.9 (3)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−1.7 (5)	C8—C9—C10—C11	−177.4 (3)
O1—C1—C2—C3	178.2 (3)	C14—C9—C10—C11	2.6 (5)
C1—C2—C3—C4	−0.4 (5)	C9—C10—C11—O2	−179.8 (3)
C2—C3—C4—C5	2.0 (5)	C9—C10—C11—C12	1.4 (5)
C2—C3—C4—C7	−175.2 (3)	O2—C11—C12—C13	150.5 (3)
C3—C4—C5—C6	−1.6 (5)	C10—C11—C12—C13	−30.7 (4)
C7—C4—C5—C6	175.7 (3)	C11—C12—C13—C14	52.6 (4)
C2—C1—C6—C5	2.0 (5)	C11—C12—C13—C15	−68.6 (4)
O1—C1—C6—C5	−177.8 (3)	C11—C12—C13—C16	171.0 (3)
C4—C5—C6—C1	−0.3 (5)	C10—C9—C14—C13	23.3 (5)
C5—C4—C7—C8	174.1 (3)	C8—C9—C14—C13	−156.6 (3)
C3—C4—C7—C8	−8.8 (5)	C15—C13—C14—C9	71.2 (4)
C4—C7—C8—C9	176.1 (3)	C16—C13—C14—C9	−167.4 (3)
C7—C8—C9—C10	174.5 (3)	C12—C13—C14—C9	−49.0 (4)
C7—C8—C9—C14	−5.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.91	2.718 (3)	166

Symmetry code: (i) x+1/2, −y−1/2, z−1/2.