(1R,2S,5R)-2-Iso­propyl-5-methyl­cyclo­hexyl (2S,3S)-3-phenyl­oxirane-2-carboxyl­ate

The title compound, C₁₉H₂₆O₃, was synthesized from (1R,2S,5R)-2-iso­propyl-5-methyl­cyclo­hexyl chloro­acetate and benz­aldehyde via the well known Darzen reaction. The absolute configuration was determined from the synthetic precursor. Non-classical C—H...O hydrogen bonds link the mol­ecules in the crystal structure into a sheet parallel to (001).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.123
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O2      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O2      ..       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  O1      ..       2.69 Ang.

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           27.23
           From the CIF: _reflns_number_total               2312
           Count of symmetry unique reflns         2315
           Completeness (_total/calc)             99.87%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (2S,3S)-3-phenyloxirane-2-carboxylate

Crystal data

C19H26O3	Dx = 1.132 Mg m^−3
Mr = 302.4	Melting point: 104 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 17363 reflections
a = 5.6507 (6) Å	θ = 1.8–27.3°
b = 12.8745 (17) Å	µ = 0.08 mm^−1
c = 24.386 (3) Å	T = 293 K
V = 1774.1 (4) Å^3	Prism, colorless
Z = 4	0.7 × 0.38 × 0.23 mm
F(000) = 656

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.054
Detector resolution: 10.00 pixels mm^-1	θmax = 27.2°, θmin = 2.3°
ω scans	h = −7→7
14189 measured reflections	k = −16→16
2312 independent reflections	l = −31→30
1675 reflections with I > 2σ(I)

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.1274P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.047	(Δ/σ)max < 0.001
wR(F^2) = 0.124	Δρmax = 0.13 e Å^−3
S = 1.02	Δρmin = −0.12 e Å^−3
2312 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
203 parameters	Extinction coefficient: 0.023 (3)
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
C1	0.3969 (4)	0.35533 (17)	0.13176 (9)	0.0557 (5)
C2	0.1558 (4)	0.3274 (2)	0.15209 (10)	0.0637 (6)
H2	0.0293	0.3241	0.1246	0.076*
C3	0.0868 (4)	0.35831 (18)	0.20759 (10)	0.0637 (6)
H3	−0.0826	0.3716	0.2126	0.076*
C4	0.2445 (4)	0.41691 (19)	0.24467 (9)	0.0575 (6)
C5	0.1872 (5)	0.5177 (2)	0.25721 (11)	0.0709 (7)
H5	0.0486	0.5465	0.2434	0.085*
C6	0.3327 (6)	0.5764 (2)	0.28993 (12)	0.0835 (8)
H6	0.2927	0.6449	0.2978	0.1*
C7	0.5348 (6)	0.5352 (3)	0.31091 (12)	0.0860 (9)
H7	0.6336	0.5756	0.3327	0.103*
C8	0.5923 (5)	0.4348 (3)	0.29991 (11)	0.0809 (8)
H8	0.729	0.4061	0.3148	0.097*
C9	0.4476 (5)	0.3751 (2)	0.26649 (10)	0.0682 (7)
H9	0.488	0.3066	0.2588	0.082*
C10	0.6001 (4)	0.48769 (19)	0.08178 (9)	0.0614 (6)
H10	0.7271	0.4359	0.0827	0.074*
C11	0.6610 (5)	0.5744 (2)	0.12059 (10)	0.0731 (7)
H11A	0.6819	0.5463	0.1572	0.088*
H11B	0.531	0.6235	0.1218	0.088*
C12	0.8851 (6)	0.6306 (2)	0.10349 (12)	0.0791 (8)
H12	1.0157	0.5806	0.1043	0.095*
C13	0.9468 (9)	0.7197 (3)	0.14215 (16)	0.1204 (14)
H13A	0.8207	0.7697	0.1421	0.181*
H13B	1.0904	0.7523	0.1301	0.181*
H13C	0.9681	0.6931	0.1786	0.181*
C14	0.8575 (7)	0.6683 (2)	0.04544 (13)	0.0941 (10)
H14A	1.0048	0.6997	0.0334	0.113*
H14B	0.7357	0.7214	0.0442	0.113*
C15	0.7922 (7)	0.5817 (3)	0.00672 (12)	0.0923 (10)
H15A	0.9224	0.5327	0.0049	0.111*
H15B	0.7699	0.6103	−0.0297	0.111*
C16	0.5665 (5)	0.5234 (2)	0.02368 (10)	0.0721 (7)
H16	0.4376	0.5743	0.0239	0.087*
C17	0.4926 (7)	0.4362 (3)	−0.01516 (12)	0.0962 (10)
H17	0.3534	0.4031	0.0012	0.115*
C18	0.6787 (10)	0.3521 (3)	−0.02126 (18)	0.1379 (17)
H18A	0.6191	0.2979	−0.0445	0.207*
H18B	0.7159	0.3239	0.0142	0.207*
H18C	0.819	0.3812	−0.0373	0.207*
C19	0.4147 (9)	0.4786 (5)	−0.07110 (14)	0.1505 (19)
H19A	0.5507	0.5026	−0.091	0.226*
H19B	0.3064	0.5352	−0.0658	0.226*
H19C	0.338	0.4244	−0.0915	0.226*
O1	0.1465 (3)	0.25354 (13)	0.19492 (7)	0.0766 (5)
O2	0.5762 (3)	0.31145 (14)	0.14234 (8)	0.0746 (5)
O3	0.3811 (3)	0.43912 (14)	0.10025 (7)	0.0669 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0517 (12)	0.0571 (13)	0.0583 (12)	0.0017 (11)	−0.0036 (11)	−0.0044 (10)
C2	0.0514 (12)	0.0688 (15)	0.0711 (14)	−0.0071 (11)	−0.0041 (12)	−0.0038 (12)
C3	0.0488 (12)	0.0634 (14)	0.0788 (15)	−0.0097 (11)	0.0078 (12)	0.0002 (12)
C4	0.0506 (12)	0.0640 (14)	0.0578 (12)	−0.0049 (11)	0.0091 (11)	0.0056 (11)
C5	0.0686 (16)	0.0659 (15)	0.0782 (15)	0.0039 (13)	0.0028 (14)	0.0016 (14)
C6	0.095 (2)	0.0670 (17)	0.0885 (18)	−0.0022 (16)	0.0067 (18)	−0.0126 (15)
C7	0.089 (2)	0.093 (2)	0.0757 (17)	−0.0174 (18)	0.0018 (17)	−0.0166 (15)
C8	0.0650 (16)	0.105 (2)	0.0721 (15)	0.0016 (16)	−0.0079 (15)	−0.0010 (16)
C9	0.0633 (16)	0.0691 (15)	0.0722 (15)	0.0055 (13)	0.0077 (13)	0.0005 (13)
C10	0.0507 (12)	0.0629 (14)	0.0707 (13)	0.0102 (11)	0.0087 (12)	0.0094 (11)
C11	0.0759 (17)	0.0716 (16)	0.0719 (14)	0.0067 (14)	0.0003 (14)	0.0076 (14)
C12	0.0737 (17)	0.0639 (15)	0.0997 (19)	−0.0004 (14)	−0.0012 (17)	0.0060 (14)
C13	0.138 (3)	0.082 (2)	0.140 (3)	−0.021 (2)	−0.016 (3)	−0.009 (2)
C14	0.098 (2)	0.0778 (19)	0.107 (2)	−0.0112 (18)	0.017 (2)	0.0148 (17)
C15	0.099 (2)	0.099 (2)	0.0793 (18)	−0.0008 (19)	0.0260 (17)	0.0148 (17)
C16	0.0714 (17)	0.0784 (16)	0.0666 (14)	0.0123 (14)	0.0097 (14)	0.0085 (13)
C17	0.099 (2)	0.115 (2)	0.0740 (17)	−0.003 (2)	0.0060 (18)	−0.0069 (19)
C18	0.163 (4)	0.117 (3)	0.134 (3)	0.015 (3)	0.008 (3)	−0.056 (3)
C19	0.166 (4)	0.214 (5)	0.0722 (19)	−0.005 (5)	−0.006 (3)	0.000 (3)
O1	0.0745 (11)	0.0586 (10)	0.0967 (12)	−0.0197 (9)	0.0095 (11)	0.0020 (9)
O2	0.0546 (10)	0.0720 (11)	0.0972 (13)	0.0066 (9)	0.0022 (9)	0.0199 (10)
O3	0.0499 (9)	0.0732 (11)	0.0776 (10)	0.0087 (8)	0.0049 (9)	0.0144 (9)

Geometric parameters (Å, º)

C1—O2	1.188 (3)	C11—H11A	0.97
C1—O3	1.328 (3)	C11—H11B	0.97
C1—C2	1.494 (3)	C12—C14	1.505 (4)
C2—O1	1.413 (3)	C12—C13	1.525 (4)
C2—C3	1.464 (3)	C12—H12	0.98
C2—H2	0.98	C13—H13A	0.96
C3—O1	1.424 (3)	C13—H13B	0.96
C3—C4	1.477 (3)	C13—H13C	0.96
C3—H3	0.98	C14—C15	1.507 (4)
C4—C5	1.372 (4)	C14—H14A	0.97
C4—C9	1.375 (4)	C14—H14B	0.97
C5—C6	1.372 (4)	C15—C16	1.536 (4)
C5—H5	0.93	C15—H15A	0.97
C6—C7	1.360 (4)	C15—H15B	0.97
C6—H6	0.93	C16—C17	1.527 (4)
C7—C8	1.359 (4)	C16—H16	0.98
C7—H7	0.93	C17—C18	1.517 (5)
C8—C9	1.387 (4)	C17—C19	1.534 (5)
C8—H8	0.93	C17—H17	0.98
C9—H9	0.93	C18—H18A	0.96
C10—O3	1.458 (3)	C18—H18B	0.96
C10—C16	1.501 (3)	C18—H18C	0.96
C10—C11	1.504 (4)	C19—H19A	0.96
C10—H10	0.98	C19—H19B	0.96
C11—C12	1.517 (4)	C19—H19C	0.96
O2—C1—O3	124.7 (2)	C14—C12—H12	108
O2—C1—C2	126.2 (2)	C11—C12—H12	108
O3—C1—C2	109.0 (2)	C13—C12—H12	108
O1—C2—C3	59.32 (15)	C12—C13—H13A	109.5
O1—C2—C1	116.2 (2)	C12—C13—H13B	109.5
C3—C2—C1	119.0 (2)	H13A—C13—H13B	109.5
O1—C2—H2	116.7	C12—C13—H13C	109.5
C3—C2—H2	116.7	H13A—C13—H13C	109.5
C1—C2—H2	116.7	H13B—C13—H13C	109.5
O1—C3—C2	58.59 (16)	C12—C14—C15	112.1 (2)
O1—C3—C4	118.3 (2)	C12—C14—H14A	109.2
C2—C3—C4	123.0 (2)	C15—C14—H14A	109.2
O1—C3—H3	115.1	C12—C14—H14B	109.2
C2—C3—H3	115.1	C15—C14—H14B	109.2
C4—C3—H3	115.1	H14A—C14—H14B	107.9
C5—C4—C9	118.7 (2)	C14—C15—C16	113.3 (3)
C5—C4—C3	118.5 (2)	C14—C15—H15A	108.9
C9—C4—C3	122.7 (2)	C16—C15—H15A	108.9
C4—C5—C6	120.6 (3)	C14—C15—H15B	108.9
C4—C5—H5	119.7	C16—C15—H15B	108.9
C6—C5—H5	119.7	H15A—C15—H15B	107.7
C7—C6—C5	120.4 (3)	C10—C16—C17	113.2 (2)
C7—C6—H6	119.8	C10—C16—C15	107.4 (2)
C5—C6—H6	119.8	C17—C16—C15	114.8 (2)
C8—C7—C6	119.9 (3)	C10—C16—H16	107
C8—C7—H7	120.1	C17—C16—H16	107
C6—C7—H7	120.1	C15—C16—H16	107
C7—C8—C9	120.1 (3)	C18—C17—C16	113.3 (3)
C7—C8—H8	119.9	C18—C17—C19	111.5 (3)
C9—C8—H8	119.9	C16—C17—C19	111.6 (3)
C4—C9—C8	120.2 (3)	C18—C17—H17	106.6
C4—C9—H9	119.9	C16—C17—H17	106.6
C8—C9—H9	119.9	C19—C17—H17	106.6
O3—C10—C16	108.4 (2)	C17—C18—H18A	109.5
O3—C10—C11	108.57 (19)	C17—C18—H18B	109.5
C16—C10—C11	113.3 (2)	H18A—C18—H18B	109.5
O3—C10—H10	108.8	C17—C18—H18C	109.5
C16—C10—H10	108.8	H18A—C18—H18C	109.5
C11—C10—H10	108.8	H18B—C18—H18C	109.5
C10—C11—C12	111.9 (2)	C17—C19—H19A	109.5
C10—C11—H11A	109.2	C17—C19—H19B	109.5
C12—C11—H11A	109.2	H19A—C19—H19B	109.5
C10—C11—H11B	109.2	C17—C19—H19C	109.5
C12—C11—H11B	109.2	H19A—C19—H19C	109.5
H11A—C11—H11B	107.9	H19B—C19—H19C	109.5
C14—C12—C11	109.0 (2)	C2—O1—C3	62.09 (15)
C14—C12—C13	111.3 (2)	C1—O3—C10	118.04 (17)
C11—C12—C13	112.3 (3)
O2—C1—C2—O1	11.5 (4)	C10—C11—C12—C14	55.4 (3)
O3—C1—C2—O1	−167.44 (18)	C10—C11—C12—C13	179.2 (3)
O2—C1—C2—C3	79.3 (3)	C11—C12—C14—C15	−54.6 (4)
O3—C1—C2—C3	−99.6 (2)	C13—C12—C14—C15	−179.0 (3)
C1—C2—C3—O1	−104.9 (3)	C12—C14—C15—C16	56.2 (4)
O1—C2—C3—C4	105.4 (3)	O3—C10—C16—C17	−56.6 (3)
C1—C2—C3—C4	0.4 (4)	C11—C10—C16—C17	−177.1 (2)
O1—C3—C4—C5	−179.7 (2)	O3—C10—C16—C15	175.7 (2)
C2—C3—C4—C5	111.2 (3)	C11—C10—C16—C15	55.1 (3)
O1—C3—C4—C9	1.2 (3)	C14—C15—C16—C10	−54.1 (3)
C2—C3—C4—C9	−67.9 (3)	C14—C15—C16—C17	179.0 (3)
C9—C4—C5—C6	1.5 (4)	C10—C16—C17—C18	−64.0 (4)
C3—C4—C5—C6	−177.7 (2)	C15—C16—C17—C18	59.8 (4)
C4—C5—C6—C7	−0.7 (4)	C10—C16—C17—C19	169.1 (3)
C5—C6—C7—C8	−0.7 (5)	C15—C16—C17—C19	−67.0 (4)
C6—C7—C8—C9	1.2 (4)	C1—C2—O1—C3	109.6 (2)
C5—C4—C9—C8	−0.9 (4)	C4—C3—O1—C2	−113.3 (2)
C3—C4—C9—C8	178.2 (2)	O2—C1—O3—C10	−6.8 (3)
C7—C8—C9—C4	−0.5 (4)	C2—C1—O3—C10	172.24 (19)
O3—C10—C11—C12	−178.8 (2)	C16—C10—O3—C1	141.5 (2)
C16—C10—C11—C12	−58.3 (3)	C11—C10—O3—C1	−95.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2^i	0.98	2.60	3.290 (4)	127
C3—H3···O2^i	0.98	2.69	3.350 (4)	125
C6—H6···O2^ii	0.93	2.70	3.486 (4)	143
C7—H7···O1^ii	0.93	2.69	3.342 (5)	128

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