(1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenyl­ethyl)cyclo­hexyl chloro­acetate

The title compound, C₁₈H₂₅ClO₂, is an inter­mediate for the chiral auxiliary (-)-8-phenyl­menthol en route from (R)-(+)-pulegone. Its crystal structure was determined in order to relate the stereochemistry of the compound to that of other 8-aryl­menthol esters. The compound crystallizes with an unusually elongated unit cell, c:a = 42.287:8.8672.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.085
• Data-to-parameter ratio = 25.2

checkCIF/PLATON results

No syntax errors found



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           29.99
           From the CIF: _reflns_number_total               4856
           Count of symmetry unique reflns         2935
           Completeness (_total/calc)            165.45%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1921
           Fraction of Friedel pairs measured     0.655
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT, SADABS (Bruker, 2003) and XPREP (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate

Crystal data

C18H25ClO2	Dx = 1.234 Mg m^−3
Mr = 308.83	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212	Cell parameters from 9776 reflections
Hall symbol: P 4nw 2abw	θ = 2.5–29.9°
a = 8.8672 (4) Å	µ = 0.23 mm^−1
c = 42.287 (2) Å	T = 100 K
V = 3324.9 (3) Å^3	Block, colourless
Z = 8	0.48 × 0.36 × 0.28 mm
F(000) = 1328

Data collection

Bruker SMART CCD diffractometer	4760 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
ω scans	θmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→12
Tmin = 0.862, Tmax = 0.937	k = −12→12
49620 measured reflections	l = −59→59
4856 independent reflections

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 0.6838P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
4856 reflections	Δρmax = 0.34 e Å^−3
193 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1992 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (4)

Special details

Experimental. Bruker Smart APEX CCD 3-axis diffractometer, full sphere data collection with 4 x 600 frames of 0.3deg and 10sec per frame.

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
Cl	0.94480 (4)	0.60965 (4)	0.283793 (8)	0.03237 (9)
O1	0.66961 (9)	0.49977 (9)	0.215786 (17)	0.01573 (15)
O2	0.74406 (12)	0.72694 (10)	0.23413 (2)	0.0305 (2)
C1	0.71805 (14)	0.15325 (13)	0.17216 (3)	0.0204 (2)
H1	0.6262	0.1402	0.1609	0.024*
C2	0.77296 (16)	0.03505 (14)	0.19035 (3)	0.0262 (3)
H2	0.7188	−0.0572	0.1914	0.031*
C3	0.90658 (16)	0.05144 (16)	0.20694 (3)	0.0297 (3)
H3	0.9437	−0.0286	0.2197	0.036*
C4	0.98539 (15)	0.18557 (17)	0.20477 (3)	0.0285 (3)
H4	1.0776	0.1972	0.2159	0.034*
C5	0.93037 (14)	0.30420 (15)	0.18629 (3)	0.0225 (2)
H5	0.9866	0.3951	0.1849	0.027*
C6	0.79445 (12)	0.29148 (13)	0.16994 (2)	0.01680 (19)
C7	0.72817 (12)	0.41811 (12)	0.14940 (2)	0.01607 (19)
C8	0.57001 (12)	0.46552 (11)	0.16281 (2)	0.01472 (18)
H8	0.5188	0.3713	0.1701	0.018*
C9	0.46511 (13)	0.54044 (13)	0.13828 (2)	0.0190 (2)
H9A	0.5121	0.6350	0.1307	0.023*
H9B	0.4530	0.4722	0.1199	0.023*
C10	0.30965 (13)	0.57603 (13)	0.15216 (3)	0.0197 (2)
H10A	0.2464	0.6241	0.1357	0.024*
H10B	0.2600	0.4808	0.1586	0.024*
C11	0.32055 (13)	0.68087 (12)	0.18077 (3)	0.0188 (2)
H11	0.3674	0.7777	0.1737	0.023*
C12	0.42463 (12)	0.60876 (13)	0.20528 (2)	0.01792 (19)
H12A	0.4375	0.6786	0.2233	0.022*
H12B	0.3777	0.5150	0.2133	0.022*
C13	0.57834 (12)	0.57209 (12)	0.19125 (2)	0.01523 (18)
H13	0.6285	0.6680	0.1846	0.018*
C14	0.71283 (15)	0.35463 (14)	0.11554 (3)	0.0234 (2)
H14A	0.6347	0.2765	0.1152	0.035*
H14B	0.8093	0.3109	0.1089	0.035*
H14C	0.6848	0.4362	0.1010	0.035*
C15	0.83442 (14)	0.55453 (14)	0.14729 (3)	0.0234 (2)
H15A	0.7874	0.6334	0.1344	0.035*
H15B	0.9298	0.5236	0.1376	0.035*
H15C	0.8538	0.5937	0.1686	0.035*
C16	0.16719 (14)	0.71684 (15)	0.19524 (3)	0.0271 (2)
H16A	0.1806	0.7850	0.2133	0.041*
H16B	0.1193	0.6233	0.2024	0.041*
H16C	0.1031	0.7654	0.1793	0.041*
C17	0.74609 (12)	0.59205 (12)	0.23521 (2)	0.01681 (19)
C18	0.83315 (13)	0.49682 (12)	0.25863 (2)	0.01823 (19)
H18A	0.8988	0.4255	0.2470	0.022*
H18B	0.7615	0.4371	0.2715	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.04062 (18)	0.02398 (14)	0.03249 (15)	−0.00522 (12)	−0.02306 (14)	0.00014 (12)
O1	0.0191 (4)	0.0149 (3)	0.0132 (3)	0.0004 (3)	−0.0048 (3)	0.0000 (3)
O2	0.0453 (6)	0.0160 (4)	0.0302 (5)	−0.0037 (4)	−0.0182 (4)	0.0016 (3)
C1	0.0227 (5)	0.0193 (5)	0.0192 (5)	0.0024 (4)	0.0035 (4)	−0.0008 (4)
C2	0.0346 (6)	0.0198 (5)	0.0242 (5)	0.0071 (5)	0.0093 (5)	0.0021 (4)
C3	0.0383 (7)	0.0306 (6)	0.0202 (5)	0.0201 (6)	0.0049 (5)	0.0036 (5)
C4	0.0241 (6)	0.0398 (7)	0.0214 (5)	0.0138 (5)	−0.0022 (5)	−0.0024 (5)
C5	0.0191 (5)	0.0281 (6)	0.0204 (5)	0.0042 (4)	0.0002 (4)	−0.0032 (4)
C6	0.0176 (5)	0.0188 (5)	0.0140 (4)	0.0035 (4)	0.0022 (4)	−0.0004 (3)
C7	0.0166 (4)	0.0174 (5)	0.0142 (4)	−0.0004 (4)	−0.0004 (3)	0.0006 (3)
C8	0.0169 (4)	0.0145 (4)	0.0127 (4)	−0.0001 (3)	−0.0022 (3)	0.0000 (3)
C9	0.0225 (5)	0.0202 (5)	0.0142 (4)	0.0012 (4)	−0.0050 (4)	0.0000 (4)
C10	0.0195 (5)	0.0178 (5)	0.0219 (5)	0.0014 (4)	−0.0070 (4)	−0.0015 (4)
C11	0.0181 (5)	0.0154 (5)	0.0230 (5)	0.0020 (4)	−0.0047 (4)	−0.0018 (4)
C12	0.0189 (5)	0.0184 (4)	0.0165 (4)	0.0026 (4)	−0.0009 (4)	−0.0013 (4)
C13	0.0177 (4)	0.0149 (4)	0.0131 (4)	0.0006 (3)	−0.0036 (3)	0.0006 (3)
C14	0.0287 (6)	0.0275 (6)	0.0140 (4)	0.0038 (5)	0.0004 (4)	−0.0017 (4)
C15	0.0230 (5)	0.0225 (5)	0.0247 (5)	−0.0043 (4)	0.0030 (4)	0.0039 (4)
C16	0.0195 (5)	0.0266 (6)	0.0352 (6)	0.0048 (4)	−0.0048 (5)	−0.0073 (5)
C17	0.0188 (5)	0.0180 (5)	0.0136 (4)	−0.0010 (4)	−0.0034 (3)	−0.0003 (4)
C18	0.0206 (5)	0.0171 (5)	0.0170 (4)	−0.0011 (4)	−0.0070 (4)	−0.0011 (4)

Geometric parameters (Å, º)

Cl—C18	1.7644 (11)	C9—H9B	0.9900
O1—C17	1.3432 (12)	C10—C11	1.5288 (16)
O1—C13	1.4638 (12)	C10—H10A	0.9900
O2—C17	1.1970 (14)	C10—H10B	0.9900
C1—C2	1.3883 (17)	C11—C16	1.5250 (17)
C1—C6	1.4036 (16)	C11—C12	1.5279 (15)
C1—H1	0.9500	C11—H11	1.0000
C2—C3	1.384 (2)	C12—C13	1.5216 (15)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.382 (2)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13	1.0000
C4—C5	1.3983 (18)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—C6	1.3942 (16)	C14—H14C	0.9800
C5—H5	0.9500	C15—H15A	0.9800
C6—C7	1.5364 (15)	C15—H15B	0.9800
C7—C15	1.5359 (16)	C15—H15C	0.9800
C7—C14	1.5442 (15)	C16—H16A	0.9800
C7—C8	1.5701 (15)	C16—H16B	0.9800
C8—C13	1.5313 (14)	C16—H16C	0.9800
C8—C9	1.5436 (14)	C17—C18	1.5133 (15)
C8—H8	1.0000	C18—H18A	0.9900
C9—C10	1.5312 (16)	C18—H18B	0.9900
C9—H9A	0.9900
C13—O1—C17	116.46 (8)	C11—C10—H10B	109.3
O1—C17—O2	125.30 (10)	C9—C10—H10B	109.3
O1—C17—C18	108.53 (9)	H10A—C10—H10B	107.9
O2—C17—C18	126.17 (10)	C16—C11—C12	110.73 (10)
C17—C18—Cl	111.38 (8)	C16—C11—C10	112.86 (10)
C2—C1—C6	121.81 (11)	C12—C11—C10	108.69 (9)
C2—C1—H1	119.1	C16—C11—H11	108.1
C6—C1—H1	119.1	C12—C11—H11	108.1
C3—C2—C1	120.11 (12)	C10—C11—H11	108.1
C3—C2—H2	119.9	C13—C12—C11	111.48 (9)
C1—C2—H2	119.9	C13—C12—H12A	109.3
C4—C3—C2	119.30 (12)	C11—C12—H12A	109.3
C4—C3—H3	120.4	C13—C12—H12B	109.3
C2—C3—H3	120.4	C11—C12—H12B	109.3
C3—C4—C5	120.52 (12)	H12A—C12—H12B	108.0
C3—C4—H4	119.7	O1—C13—C12	108.22 (8)
C5—C4—H4	119.7	O1—C13—C8	108.24 (8)
C6—C5—C4	121.20 (12)	C12—C13—C8	113.25 (8)
C6—C5—H5	119.4	O1—C13—H13	109.0
C4—C5—H5	119.4	C12—C13—H13	109.0
C5—C6—C1	117.04 (10)	C8—C13—H13	109.0
C5—C6—C7	123.50 (10)	C7—C14—H14A	109.5
C1—C6—C7	119.43 (10)	C7—C14—H14B	109.5
C15—C7—C6	111.95 (9)	H14A—C14—H14B	109.5
C15—C7—C14	106.69 (9)	C7—C14—H14C	109.5
C6—C7—C14	106.94 (9)	H14A—C14—H14C	109.5
C15—C7—C8	110.98 (9)	H14B—C14—H14C	109.5
C6—C7—C8	109.46 (8)	C7—C15—H15A	109.5
C14—C7—C8	110.72 (9)	C7—C15—H15B	109.5
C13—C8—C9	106.93 (8)	H15A—C15—H15B	109.5
C13—C8—C7	113.95 (8)	C7—C15—H15C	109.5
C9—C8—C7	114.25 (8)	H15A—C15—H15C	109.5
C13—C8—H8	107.1	H15B—C15—H15C	109.5
C9—C8—H8	107.1	C11—C16—H16A	109.5
C7—C8—H8	107.1	C11—C16—H16B	109.5
C10—C9—C8	111.93 (9)	H16A—C16—H16B	109.5
C10—C9—H9A	109.2	C11—C16—H16C	109.5
C8—C9—H9A	109.2	H16A—C16—H16C	109.5
C10—C9—H9B	109.2	H16B—C16—H16C	109.5
C8—C9—H9B	109.2	C17—C18—H18A	109.4
H9A—C9—H9B	107.9	Cl—C18—H18A	109.4
C11—C10—C9	111.83 (9)	C17—C18—H18B	109.4
C11—C10—H10A	109.3	Cl—C18—H18B	109.4
C9—C10—H10A	109.3	H18A—C18—H18B	108.0
C13—C8—C7—C6	80.20 (11)	C6—C7—C8—C9	−156.46 (9)
C8—C13—O1—C17	150.65 (9)	C14—C7—C8—C9	−38.81 (12)
O1—C17—C18—Cl	176.92 (8)	C13—C8—C9—C10	−56.20 (11)
C6—C1—C2—C3	−0.04 (17)	C7—C8—C9—C10	176.76 (9)
C1—C2—C3—C4	−0.97 (18)	C8—C9—C10—C11	58.72 (12)
C2—C3—C4—C5	0.60 (18)	C9—C10—C11—C16	−179.44 (10)
C3—C4—C5—C6	0.80 (18)	C9—C10—C11—C12	−56.20 (12)
C4—C5—C6—C1	−1.75 (16)	C16—C11—C12—C13	−179.98 (9)
C4—C5—C6—C7	179.76 (10)	C10—C11—C12—C13	55.52 (12)
C2—C1—C6—C5	1.39 (16)	C17—O1—C13—C12	−86.25 (11)
C2—C1—C6—C7	179.94 (10)	C11—C12—C13—O1	−178.39 (8)
C5—C6—C7—C15	3.97 (14)	C11—C12—C13—C8	−58.39 (11)
C1—C6—C7—C15	−174.49 (10)	C9—C8—C13—O1	176.51 (8)
C5—C6—C7—C14	120.49 (11)	C7—C8—C13—O1	−56.26 (11)
C1—C6—C7—C14	−57.97 (12)	C9—C8—C13—C12	56.53 (11)
C5—C6—C7—C8	−119.52 (11)	C7—C8—C13—C12	−176.25 (8)
C1—C6—C7—C8	62.03 (12)	C13—O1—C17—O2	0.71 (16)
C15—C7—C8—C13	−43.86 (12)	C13—O1—C17—C18	−179.82 (9)
C14—C7—C8—C13	−162.15 (9)	O2—C17—C18—Cl	−3.60 (16)
C15—C7—C8—C9	79.48 (11)