(3'R,4S)-3-(3'-Cyclo­hexyl-3'-phenyl­propionyl)-5,5-dimethyl-4-phenyl­oxazolidin-2-one

The title compound, C₂₆H₃₁NO₃, was prepared with high stereoselectivity via asymmetric Michael addition, and characterized by NMR, HRMS and FT-IR spectroscopic analysis, and by single-crystal X-ray diffraction. All bond lengths and angles are within expected ranges and the absolute configuration is as expected.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.101
• Data-to-parameter ratio = 11.2

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           27.50
           From the CIF: _reflns_number_total               3028
           Count of symmetry unique reflns         3030
           Completeness (_total/calc)             99.93%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 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
   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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(3'R, 4S)-3-(3'-Cyclohexyl-3'-phenylpropionyl)-5,5-dimethyl-4- phenyloxazolidin-2-one

Crystal data

C26H31NO3	F(000) = 872
Mr = 405.52	Dx = 1.151 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4623 reflections
a = 10.1004 (2) Å	θ = 1.9–28.6°
b = 14.8636 (3) Å	µ = 0.07 mm^−1
c = 15.5876 (3) Å	T = 273 K
V = 2340.14 (8) Å^3	Block, colourless
Z = 4	0.30 × 0.28 × 0.26 mm

Data collection

Bruker APEX-II CCD area-detector diffractometer	3028 independent reflections
Radiation source: fine-focus sealed tube	2408 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→12
Tmin = 0.977, Tmax = 0.977	k = −19→19
20759 measured reflections	l = −20→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 0.179P] where P = (Fo^2 + 2Fc^2)/3
3028 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.10 e Å^−3
0 restraints	Δρmin = −0.11 e Å^−3

Special details

Experimental. Spectroscopic analysis: IR (KBr, ν cm^-1): 3044, 2929, 1771, 1692, 1600, 1363, 1322, 1215, 1157, 700; ¹HNMR (CDCl₃, δ, p.p.m.): 7.31–7.03 (m, 10H, aromatic protons), 4.79 (s, 1H, oxazolidinone, PhCH–), 3.74–3.68 (dd, 1H, –C_alphaH–), 3.19–3.15 (dd, 1H, –C_betaH–), 2.99–2.94 (m, 1H, –C_betaH–), 1.84–0.74 (m, 11H, cyclohexyl proton), 1.21 (s, 1H, oxazolidinone, –CH3), 0.82 (s, 1H, oxazolidinone, –CH3); ¹³CNMR (CDCl₃, δ, p.p.m.): 172.4, 153.3, 143.1, 136.3, 128.8, 128.5, 128.1, 126.3, 82.2, 66.9, 48.2, 43.0, 38.3, 31.1, 30.8, 28.4, 26.4, 23.5; High resolution MS for C₂₆H₃₁NO₃: [M+Na]⁺ (calcd. 428.2201; found: 428.2239); m.p.403–404 K; [alpha]_D²⁰=+94.439 (c = 1.025, CHCl₃).

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	0.95858 (16)	1.07800 (9)	0.84651 (10)	0.0627 (4)
O2	0.57851 (16)	1.06330 (11)	0.95809 (13)	0.0820 (6)
O3	0.64346 (14)	1.19687 (10)	1.00811 (10)	0.0624 (4)
N1	0.78455 (16)	1.12548 (10)	0.92251 (11)	0.0489 (4)
C1	0.9046 (2)	0.93396 (12)	1.02559 (12)	0.0436 (4)
C2	1.0225 (2)	0.96553 (13)	1.05920 (13)	0.0530 (5)
H2	1.0973	0.9680	1.0245	0.064*
C3	1.0306 (3)	0.99364 (16)	1.14429 (15)	0.0686 (7)
H3	1.1103	1.0154	1.1659	0.082*
C4	0.9214 (3)	0.98917 (17)	1.19620 (14)	0.0724 (7)
H4	0.9272	1.0063	1.2535	0.087*
C5	0.8040 (3)	0.95939 (18)	1.16340 (14)	0.0717 (7)
H5	0.7295	0.9573	1.1983	0.086*
C6	0.7950 (2)	0.93241 (16)	1.07891 (14)	0.0612 (6)
H6	0.7140	0.9129	1.0574	0.073*
C7	0.8964 (2)	0.90153 (12)	0.93328 (12)	0.0431 (4)
H7	0.9852	0.9065	0.9085	0.052*
C8	0.8549 (2)	0.80183 (12)	0.92787 (12)	0.0472 (4)
H8	0.7664	0.7963	0.9530	0.057*
C9	0.9488 (3)	0.74230 (14)	0.97951 (15)	0.0630 (6)
H9A	1.0376	0.7477	0.9563	0.076*
H9B	0.9509	0.7630	1.0385	0.076*
C10	0.9071 (3)	0.64421 (14)	0.97764 (17)	0.0778 (7)
H10A	0.9707	0.6085	1.0095	0.093*
H10B	0.8216	0.6379	1.0053	0.093*
C11	0.8984 (3)	0.60956 (15)	0.88734 (19)	0.0849 (8)
H11A	0.8649	0.5484	0.8881	0.102*
H11B	0.9863	0.6084	0.8623	0.102*
C12	0.8092 (3)	0.66701 (16)	0.83271 (16)	0.0800 (8)
H12A	0.7187	0.6606	0.8525	0.096*
H12B	0.8131	0.6461	0.7738	0.096*
C13	0.8485 (3)	0.76625 (14)	0.83578 (14)	0.0662 (6)
H13A	0.7846	0.8013	0.8035	0.079*
H13B	0.9343	0.7737	0.8088	0.079*
C14	0.8040 (2)	0.96288 (13)	0.88074 (13)	0.0515 (5)
H14A	0.7985	0.9408	0.8223	0.062*
H14B	0.7158	0.9614	0.9053	0.062*
C15	0.8545 (2)	1.05799 (13)	0.88037 (12)	0.0476 (5)
C16	0.6612 (2)	1.12070 (14)	0.96230 (15)	0.0577 (5)
C17	0.7678 (2)	1.24920 (15)	1.01162 (14)	0.0520 (5)
C18	0.8426 (3)	1.21989 (19)	1.09074 (14)	0.0737 (7)
H18A	0.7970	1.2407	1.1410	0.111*
H18B	0.9302	1.2450	1.0895	0.111*
H18C	0.8483	1.1554	1.0919	0.111*
C19	0.7297 (3)	1.34734 (14)	1.01488 (15)	0.0644 (6)
H19A	0.6876	1.3601	1.0687	0.097*
H19B	0.6697	1.3606	0.9688	0.097*
H19C	0.8077	1.3838	1.0092	0.097*
C20	0.8382 (2)	1.21741 (12)	0.92876 (12)	0.0449 (4)
H20	0.9339	1.2146	0.9388	0.054*
C21	0.8109 (2)	1.27271 (12)	0.84888 (12)	0.0487 (5)
C22	0.8901 (2)	1.34661 (14)	0.83156 (14)	0.0581 (6)
H22	0.9605	1.3601	0.8678	0.070*
C23	0.8658 (3)	1.40067 (15)	0.76100 (15)	0.0687 (7)
H23	0.9200	1.4500	0.7501	0.082*
C24	0.7630 (3)	1.38185 (18)	0.70749 (15)	0.0802 (8)
H24	0.7469	1.4183	0.6601	0.096*
C25	0.6830 (3)	1.3090 (2)	0.72339 (16)	0.0864 (9)
H25	0.6125	1.2964	0.6869	0.104*
C26	0.7069 (3)	1.25385 (16)	0.79397 (14)	0.0674 (6)
H26	0.6529	1.2043	0.8042	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0732 (10)	0.0484 (8)	0.0665 (9)	0.0021 (8)	0.0249 (9)	−0.0012 (7)
O2	0.0584 (9)	0.0598 (9)	0.1277 (16)	−0.0114 (8)	0.0165 (10)	0.0046 (10)
O3	0.0511 (8)	0.0582 (8)	0.0781 (10)	0.0016 (7)	0.0178 (8)	0.0009 (8)
N1	0.0486 (9)	0.0372 (8)	0.0609 (10)	0.0000 (7)	0.0086 (8)	0.0023 (7)
C1	0.0526 (10)	0.0362 (8)	0.0421 (9)	0.0008 (8)	0.0009 (9)	0.0011 (8)
C2	0.0533 (11)	0.0497 (11)	0.0559 (12)	0.0004 (10)	−0.0031 (10)	−0.0054 (9)
C3	0.0718 (15)	0.0717 (15)	0.0624 (14)	0.0034 (13)	−0.0172 (13)	−0.0150 (12)
C4	0.0993 (19)	0.0782 (16)	0.0398 (11)	0.0100 (15)	−0.0062 (13)	−0.0099 (11)
C5	0.0846 (17)	0.0815 (17)	0.0490 (12)	−0.0087 (15)	0.0171 (13)	−0.0095 (11)
C6	0.0645 (14)	0.0662 (13)	0.0530 (12)	−0.0093 (12)	0.0052 (11)	−0.0070 (11)
C7	0.0494 (10)	0.0378 (9)	0.0422 (9)	−0.0017 (8)	0.0028 (9)	−0.0004 (7)
C8	0.0566 (12)	0.0392 (9)	0.0459 (10)	−0.0027 (9)	0.0059 (10)	−0.0001 (8)
C9	0.0838 (15)	0.0443 (10)	0.0609 (13)	0.0076 (11)	−0.0054 (12)	0.0000 (10)
C10	0.111 (2)	0.0422 (11)	0.0799 (16)	0.0117 (14)	0.0001 (16)	0.0055 (11)
C11	0.121 (2)	0.0406 (11)	0.0930 (19)	0.0039 (14)	0.0094 (19)	−0.0113 (12)
C12	0.117 (2)	0.0529 (13)	0.0699 (15)	−0.0160 (15)	−0.0045 (17)	−0.0142 (11)
C13	0.0991 (18)	0.0480 (11)	0.0516 (11)	−0.0111 (12)	−0.0045 (13)	−0.0043 (9)
C14	0.0644 (13)	0.0421 (10)	0.0480 (10)	−0.0021 (10)	−0.0083 (10)	0.0009 (8)
C15	0.0577 (12)	0.0428 (10)	0.0424 (9)	0.0042 (9)	−0.0009 (10)	0.0035 (8)
C16	0.0534 (12)	0.0460 (11)	0.0735 (14)	0.0033 (10)	0.0095 (11)	0.0082 (10)
C17	0.0532 (11)	0.0497 (10)	0.0530 (11)	0.0035 (9)	0.0078 (10)	0.0016 (9)
C18	0.0808 (17)	0.0859 (17)	0.0544 (13)	0.0110 (15)	0.0037 (12)	0.0080 (12)
C19	0.0745 (14)	0.0530 (12)	0.0656 (13)	0.0095 (12)	0.0133 (12)	−0.0098 (11)
C20	0.0461 (10)	0.0369 (9)	0.0517 (10)	0.0022 (8)	0.0042 (9)	−0.0001 (8)
C21	0.0602 (12)	0.0389 (10)	0.0469 (10)	0.0039 (9)	0.0080 (10)	−0.0034 (8)
C22	0.0723 (15)	0.0470 (11)	0.0548 (12)	−0.0026 (11)	0.0154 (11)	−0.0027 (9)
C23	0.0999 (19)	0.0496 (12)	0.0566 (13)	0.0021 (13)	0.0281 (14)	0.0020 (10)
C24	0.129 (2)	0.0647 (15)	0.0473 (12)	0.0172 (17)	0.0143 (15)	0.0085 (11)
C25	0.120 (2)	0.0848 (18)	0.0548 (14)	0.0056 (18)	−0.0201 (16)	−0.0054 (13)
C26	0.0863 (16)	0.0575 (13)	0.0584 (13)	−0.0083 (13)	−0.0052 (13)	−0.0024 (11)

Geometric parameters (Å, º)

O1—C15	1.214 (2)	C11—H11A	0.9700
O2—C16	1.196 (3)	C11—H11B	0.9700
O3—C16	1.351 (3)	C12—C13	1.528 (3)
O3—C17	1.478 (3)	C12—H12A	0.9700
N1—C15	1.392 (2)	C12—H12B	0.9700
N1—C16	1.393 (3)	C13—H13A	0.9700
N1—C20	1.473 (2)	C13—H13B	0.9700
C1—C2	1.383 (3)	C14—C15	1.503 (3)
C1—C6	1.385 (3)	C14—H14A	0.9700
C1—C7	1.520 (3)	C14—H14B	0.9700
C2—C3	1.393 (3)	C17—C19	1.509 (3)
C2—H2	0.9300	C17—C18	1.511 (3)
C3—C4	1.370 (4)	C17—C20	1.548 (3)
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.365 (4)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—C6	1.380 (3)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C14	1.540 (3)	C20—C21	1.517 (3)
C7—C8	1.542 (3)	C20—H20	0.9800
C7—H7	0.9800	C21—C26	1.384 (3)
C8—C9	1.527 (3)	C21—C22	1.386 (3)
C8—C13	1.531 (3)	C22—C23	1.384 (3)
C8—H8	0.9800	C22—H22	0.9300
C9—C10	1.518 (3)	C23—C24	1.361 (4)
C9—H9A	0.9700	C23—H23	0.9300
C9—H9B	0.9700	C24—C25	1.374 (4)
C10—C11	1.501 (4)	C24—H24	0.9300
C10—H10A	0.9700	C25—C26	1.393 (3)
C10—H10B	0.9700	C25—H25	0.9300
C11—C12	1.505 (4)	C26—H26	0.9300
C16—O3—C17	110.35 (16)	C12—C13—H13A	109.2
C15—N1—C16	128.83 (17)	C8—C13—H13A	109.2
C15—N1—C20	120.88 (16)	C12—C13—H13B	109.2
C16—N1—C20	110.29 (16)	C8—C13—H13B	109.2
C2—C1—C6	117.83 (18)	H13A—C13—H13B	107.9
C2—C1—C7	120.88 (18)	C15—C14—C7	110.69 (17)
C6—C1—C7	121.29 (18)	C15—C14—H14A	109.5
C1—C2—C3	120.9 (2)	C7—C14—H14A	109.5
C1—C2—H2	119.6	C15—C14—H14B	109.5
C3—C2—H2	119.6	C7—C14—H14B	109.5
C4—C3—C2	120.0 (2)	H14A—C14—H14B	108.1
C4—C3—H3	120.0	O1—C15—N1	117.93 (17)
C2—C3—H3	120.0	O1—C15—C14	121.74 (18)
C5—C4—C3	119.6 (2)	N1—C15—C14	120.27 (18)
C5—C4—H4	120.2	O2—C16—O3	122.3 (2)
C3—C4—H4	120.2	O2—C16—N1	129.5 (2)
C4—C5—C6	120.6 (2)	O3—C16—N1	108.15 (18)
C4—C5—H5	119.7	O3—C17—C19	107.08 (17)
C6—C5—H5	119.7	O3—C17—C18	107.68 (19)
C5—C6—C1	121.0 (2)	C19—C17—C18	112.2 (2)
C5—C6—H6	119.5	O3—C17—C20	101.46 (16)
C1—C6—H6	119.5	C19—C17—C20	116.10 (18)
C1—C7—C14	110.41 (15)	C18—C17—C20	111.28 (16)
C1—C7—C8	111.80 (15)	C17—C18—H18A	109.5
C14—C7—C8	112.03 (16)	C17—C18—H18B	109.5
C1—C7—H7	107.5	H18A—C18—H18B	109.5
C14—C7—H7	107.5	C17—C18—H18C	109.5
C8—C7—H7	107.5	H18A—C18—H18C	109.5
C9—C8—C13	108.68 (18)	H18B—C18—H18C	109.5
C9—C8—C7	111.06 (17)	C17—C19—H19A	109.5
C13—C8—C7	113.24 (16)	C17—C19—H19B	109.5
C9—C8—H8	107.9	H19A—C19—H19B	109.5
C13—C8—H8	107.9	C17—C19—H19C	109.5
C7—C8—H8	107.9	H19A—C19—H19C	109.5
C10—C9—C8	112.0 (2)	H19B—C19—H19C	109.5
C10—C9—H9A	109.2	N1—C20—C21	112.43 (16)
C8—C9—H9A	109.2	N1—C20—C17	99.74 (15)
C10—C9—H9B	109.2	C21—C20—C17	115.83 (15)
C8—C9—H9B	109.2	N1—C20—H20	109.5
H9A—C9—H9B	107.9	C21—C20—H20	109.5
C11—C10—C9	111.3 (2)	C17—C20—H20	109.5
C11—C10—H10A	109.4	C26—C21—C22	118.6 (2)
C9—C10—H10A	109.4	C26—C21—C20	122.39 (19)
C11—C10—H10B	109.4	C22—C21—C20	118.98 (19)
C9—C10—H10B	109.4	C23—C22—C21	120.9 (2)
H10A—C10—H10B	108.0	C23—C22—H22	119.6
C10—C11—C12	111.8 (2)	C21—C22—H22	119.6
C10—C11—H11A	109.3	C24—C23—C22	120.2 (2)
C12—C11—H11A	109.3	C24—C23—H23	119.9
C10—C11—H11B	109.3	C22—C23—H23	119.9
C12—C11—H11B	109.3	C23—C24—C25	120.0 (2)
H11A—C11—H11B	107.9	C23—C24—H24	120.0
C11—C12—C13	112.0 (2)	C25—C24—H24	120.0
C11—C12—H12A	109.2	C24—C25—C26	120.3 (3)
C13—C12—H12A	109.2	C24—C25—H25	119.9
C11—C12—H12B	109.2	C26—C25—H25	119.9
C13—C12—H12B	109.2	C21—C26—C25	120.1 (2)
H12A—C12—H12B	107.9	C21—C26—H26	120.0
C12—C13—C8	111.94 (19)	C25—C26—H26	120.0
C6—C1—C2—C3	0.8 (3)	C17—O3—C16—O2	172.1 (2)
C7—C1—C2—C3	−178.76 (18)	C17—O3—C16—N1	−9.7 (2)
C1—C2—C3—C4	0.8 (3)	C15—N1—C16—O2	−13.3 (4)
C2—C3—C4—C5	−1.8 (4)	C20—N1—C16—O2	165.9 (2)
C3—C4—C5—C6	1.1 (4)	C15—N1—C16—O3	168.77 (19)
C4—C5—C6—C1	0.6 (4)	C20—N1—C16—O3	−12.1 (2)
C2—C1—C6—C5	−1.6 (3)	C16—O3—C17—C19	147.96 (19)
C7—C1—C6—C5	178.0 (2)	C16—O3—C17—C18	−91.1 (2)
C2—C1—C7—C14	−115.3 (2)	C16—O3—C17—C20	25.8 (2)
C6—C1—C7—C14	65.2 (2)	C15—N1—C20—C21	82.7 (2)
C2—C1—C7—C8	119.3 (2)	C16—N1—C20—C21	−96.5 (2)
C6—C1—C7—C8	−60.3 (2)	C15—N1—C20—C17	−153.96 (17)
C1—C7—C8—C9	−56.2 (2)	C16—N1—C20—C17	26.8 (2)
C14—C7—C8—C9	179.31 (17)	O3—C17—C20—N1	−29.98 (18)
C1—C7—C8—C13	−178.8 (2)	C19—C17—C20—N1	−145.64 (19)
C14—C7—C8—C13	56.7 (2)	C18—C17—C20—N1	84.3 (2)
C13—C8—C9—C10	−56.8 (3)	O3—C17—C20—C21	90.9 (2)
C7—C8—C9—C10	178.01 (19)	C19—C17—C20—C21	−24.8 (3)
C8—C9—C10—C11	57.2 (3)	C18—C17—C20—C21	−154.8 (2)
C9—C10—C11—C12	−54.5 (4)	N1—C20—C21—C26	24.1 (3)
C10—C11—C12—C13	53.3 (3)	C17—C20—C21—C26	−89.7 (2)
C11—C12—C13—C8	−54.5 (3)	N1—C20—C21—C22	−158.06 (17)
C9—C8—C13—C12	55.2 (3)	C17—C20—C21—C22	88.2 (2)
C7—C8—C13—C12	179.1 (2)	C26—C21—C22—C23	0.1 (3)
C1—C7—C14—C15	60.1 (2)	C20—C21—C22—C23	−177.79 (18)
C8—C7—C14—C15	−174.55 (16)	C21—C22—C23—C24	0.1 (3)
C16—N1—C15—O1	176.6 (2)	C22—C23—C24—C25	0.0 (4)
C20—N1—C15—O1	−2.5 (3)	C23—C24—C25—C26	−0.3 (4)
C16—N1—C15—C14	−6.0 (3)	C22—C21—C26—C25	−0.5 (3)
C20—N1—C15—C14	174.94 (17)	C20—C21—C26—C25	177.4 (2)
C7—C14—C15—O1	65.1 (2)	C24—C25—C26—C21	0.5 (4)
C7—C14—C15—N1	−112.2 (2)