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In the title compound, C21H28O6, the cyclo­hexa­none ring exhibits a chair conformation. The isoprop­oxy carbonyl groups are oriented in different directions with respect to the cyclo­hexa­none ring. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into two-dimensional sheets parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001772/cv6634sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001772/cv6634Isup2.hkl
Contains datablock I

CCDC reference: 298419

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.104
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.78 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level G PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is missing. This is required for a full paper submission (but is optional for an electronic paper).
0 ALERT level A = Data missing that is essential or data in wrong format 1 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Version 1.64.05; Farrugia, 1999); software used to prepare material for publication: SHELXL97.

c-5-Hydroxy-r-2,c-4-bis(isopropoxycarbonyl)-t-5-methyl-t-3-phenylcyclohexanone top
Crystal data top
C21H28O6F(000) = 1616
Mr = 376.43Dx = 1.214 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8602 reflections
a = 35.775 (6) Åθ = 2.2–27.9°
b = 5.7948 (10) ŵ = 0.09 mm1
c = 20.174 (3) ÅT = 273 K
β = 99.893 (3)°Block, colourless
V = 4120.1 (12) Å30.19 × 0.11 × 0.09 mm
Z = 8
Data collection top
Bruker SMART APEX CCD Area Detector
diffractometer
3175 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
Detector resolution: ω pixels mm-1h = 4242
ω or φ scans?k = 66
18792 measured reflectionsl = 2323
3617 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0482P)2 + 2.014P]
where P = (Fo2 + 2Fc2)/3
3617 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.14 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.08258 (4)0.5846 (3)0.49083 (7)0.0478 (3)
C20.08280 (4)0.5717 (2)0.41527 (6)0.0397 (3)
H20.06970.70800.39380.048*
C30.12403 (3)0.5725 (2)0.40181 (6)0.0373 (3)
H30.13620.42970.42050.045*
C40.14636 (4)0.7769 (2)0.43865 (6)0.0377 (3)
H40.13550.92140.41880.045*
C50.14510 (4)0.7789 (2)0.51499 (6)0.0424 (3)
C60.10401 (4)0.7842 (3)0.52566 (7)0.0492 (3)
H6A0.10320.77760.57340.059*
H6B0.09220.92750.50810.059*
C70.06128 (4)0.3601 (2)0.38765 (6)0.0420 (3)
C80.00125 (4)0.2138 (3)0.34937 (9)0.0632 (4)
H80.00960.11370.31840.076*
C90.00756 (6)0.0779 (4)0.40980 (11)0.0877 (6)
H910.01610.01390.43170.131*
H920.02520.04460.39590.131*
H930.01760.17750.44050.131*
C100.03693 (5)0.3265 (5)0.31271 (12)0.0929 (7)
H1010.04840.41580.34390.139*
H1020.05440.20970.29280.139*
H1030.03070.42570.27810.139*
C110.18704 (4)0.7601 (2)0.42803 (6)0.0402 (3)
C120.23519 (4)0.9248 (3)0.37390 (9)0.0585 (4)
H120.25160.82580.40590.070*
C130.24964 (5)1.1634 (4)0.37998 (12)0.0829 (6)
H1310.23331.26110.34930.124*
H1320.27481.16750.36940.124*
H1330.25031.21710.42520.124*
C140.23220 (8)0.8283 (5)0.30549 (14)0.1135 (9)
H1410.22110.67730.30420.170*
H1420.25700.81780.29370.170*
H1430.21660.92700.27400.170*
C150.16713 (5)0.9816 (3)0.54955 (8)0.0590 (4)
H1510.16670.97540.59700.088*
H1520.15571.12320.53140.088*
H1530.19290.97470.54210.088*
C160.12591 (4)0.5767 (2)0.32705 (6)0.0394 (3)
C170.11161 (4)0.7606 (3)0.28676 (7)0.0514 (4)
H170.09940.88080.30490.062*
C180.11530 (5)0.7672 (3)0.21975 (8)0.0622 (4)
H180.10560.89190.19320.075*
C190.13310 (5)0.5920 (3)0.19204 (8)0.0641 (5)
H190.13560.59760.14700.077*
C200.14712 (5)0.4084 (3)0.23128 (8)0.0625 (4)
H200.15910.28840.21260.075*
C210.14363 (4)0.3997 (3)0.29861 (7)0.0501 (4)
H210.15330.27400.32480.060*
O220.02452 (3)0.40602 (18)0.37070 (5)0.0519 (3)
O210.07529 (3)0.17373 (18)0.38329 (6)0.0554 (3)
O110.06699 (4)0.4406 (2)0.51928 (6)0.0768 (4)
O510.16009 (3)0.56738 (17)0.54505 (5)0.0508 (3)
H510.17910.53160.52990.076*
O420.19687 (3)0.92937 (17)0.39085 (5)0.0515 (3)
O410.20823 (3)0.60803 (18)0.45165 (6)0.0578 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0455 (7)0.0550 (9)0.0461 (8)0.0003 (6)0.0168 (6)0.0003 (7)
C20.0398 (7)0.0396 (7)0.0407 (7)0.0041 (5)0.0098 (5)0.0007 (5)
C30.0398 (7)0.0352 (7)0.0380 (7)0.0030 (5)0.0097 (5)0.0014 (5)
C40.0420 (7)0.0337 (6)0.0378 (7)0.0025 (5)0.0080 (5)0.0024 (5)
C50.0526 (8)0.0367 (7)0.0380 (7)0.0010 (6)0.0083 (6)0.0002 (5)
C60.0587 (8)0.0520 (8)0.0402 (7)0.0027 (7)0.0177 (6)0.0058 (6)
C70.0384 (7)0.0471 (8)0.0418 (7)0.0022 (6)0.0111 (5)0.0018 (6)
C80.0443 (8)0.0749 (11)0.0699 (10)0.0116 (8)0.0089 (7)0.0106 (9)
C90.0685 (12)0.0936 (15)0.1045 (16)0.0173 (11)0.0250 (11)0.0137 (12)
C100.0495 (10)0.1256 (18)0.0968 (15)0.0074 (11)0.0062 (9)0.0009 (14)
C110.0442 (7)0.0369 (7)0.0391 (7)0.0006 (6)0.0063 (5)0.0000 (6)
C120.0463 (8)0.0586 (10)0.0760 (11)0.0048 (7)0.0258 (7)0.0124 (8)
C130.0613 (11)0.0824 (13)0.1109 (16)0.0215 (10)0.0316 (10)0.0186 (12)
C140.1160 (18)0.1129 (18)0.132 (2)0.0426 (16)0.0797 (16)0.0508 (17)
C150.0733 (10)0.0519 (9)0.0512 (8)0.0084 (8)0.0095 (7)0.0099 (7)
C160.0396 (7)0.0409 (7)0.0387 (7)0.0034 (5)0.0098 (5)0.0038 (5)
C170.0634 (9)0.0496 (8)0.0422 (7)0.0069 (7)0.0123 (6)0.0010 (6)
C180.0817 (11)0.0628 (10)0.0423 (8)0.0006 (9)0.0111 (7)0.0051 (7)
C190.0808 (11)0.0749 (12)0.0405 (8)0.0180 (9)0.0213 (8)0.0108 (8)
C200.0718 (10)0.0634 (10)0.0584 (9)0.0036 (8)0.0281 (8)0.0208 (8)
C210.0537 (8)0.0466 (8)0.0527 (8)0.0017 (6)0.0166 (6)0.0063 (6)
O220.0378 (5)0.0574 (6)0.0597 (6)0.0015 (4)0.0062 (4)0.0033 (5)
O210.0466 (6)0.0438 (6)0.0763 (7)0.0010 (5)0.0119 (5)0.0063 (5)
O110.0907 (9)0.0898 (9)0.0558 (7)0.0342 (7)0.0291 (6)0.0010 (6)
O510.0621 (6)0.0472 (6)0.0437 (5)0.0038 (5)0.0107 (5)0.0089 (4)
O420.0452 (5)0.0494 (6)0.0632 (6)0.0039 (4)0.0188 (4)0.0139 (5)
O410.0487 (6)0.0554 (6)0.0711 (7)0.0122 (5)0.0147 (5)0.0174 (5)
Geometric parameters (Å, º) top
C1—O111.2026 (17)C10—H1030.9600
C1—C61.495 (2)C11—O411.2060 (16)
C1—C21.5275 (19)C11—O421.3187 (16)
C2—C71.5033 (19)C12—O421.4692 (17)
C2—C31.5449 (17)C12—C131.474 (2)
C2—H20.9800C12—C141.476 (3)
C3—C161.5214 (17)C12—H120.9800
C3—C41.5454 (18)C13—H1310.9600
C3—H30.9800C13—H1320.9600
C4—C111.5102 (18)C13—H1330.9600
C4—C51.5485 (17)C14—H1410.9600
C4—H40.9800C14—H1420.9600
C5—O511.4302 (16)C14—H1430.9600
C5—C151.516 (2)C15—H1510.9600
C5—C61.522 (2)C15—H1520.9600
C6—H6A0.9700C15—H1530.9600
C6—H6B0.9700C16—C211.3815 (19)
C7—O211.2000 (16)C16—C171.3840 (19)
C7—O221.3279 (16)C17—C181.381 (2)
C8—O221.4627 (19)C17—H170.9300
C8—C91.501 (3)C18—C191.368 (2)
C8—C101.510 (3)C18—H180.9300
C8—H80.9800C19—C201.369 (2)
C9—H910.9600C19—H190.9300
C9—H920.9600C20—C211.386 (2)
C9—H930.9600C20—H200.9300
C10—H1010.9600C21—H210.9300
C10—H1020.9600O51—H510.8200
O11—C1—C6123.70 (13)C8—C10—H103109.5
O11—C1—C2121.66 (13)H101—C10—H103109.5
C6—C1—C2114.62 (12)H102—C10—H103109.5
C7—C2—C1108.63 (11)O41—C11—O42123.87 (12)
C7—C2—C3112.39 (10)O41—C11—C4123.14 (12)
C1—C2—C3110.12 (11)O42—C11—C4112.99 (11)
C7—C2—H2108.5O42—C12—C13106.97 (13)
C1—C2—H2108.5O42—C12—C14107.68 (15)
C3—C2—H2108.5C13—C12—C14113.66 (17)
C16—C3—C2112.37 (10)O42—C12—H12109.5
C16—C3—C4110.93 (10)C13—C12—H12109.5
C2—C3—C4110.37 (10)C14—C12—H12109.5
C16—C3—H3107.7C12—C13—H131109.5
C2—C3—H3107.7C12—C13—H132109.5
C4—C3—H3107.7H131—C13—H132109.5
C11—C4—C3108.28 (10)C12—C13—H133109.5
C11—C4—C5109.57 (10)H131—C13—H133109.5
C3—C4—C5112.53 (10)H132—C13—H133109.5
C11—C4—H4108.8C12—C14—H141109.5
C3—C4—H4108.8C12—C14—H142109.5
C5—C4—H4108.8H141—C14—H142109.5
O51—C5—C15109.98 (11)C12—C14—H143109.5
O51—C5—C6104.98 (11)H141—C14—H143109.5
C15—C5—C6110.94 (12)H142—C14—H143109.5
O51—C5—C4110.02 (10)C5—C15—H151109.5
C15—C5—C4111.20 (11)C5—C15—H152109.5
C6—C5—C4109.54 (11)H151—C15—H152109.5
C1—C6—C5110.33 (11)C5—C15—H153109.5
C1—C6—H6A109.6H151—C15—H153109.5
C5—C6—H6A109.6H152—C15—H153109.5
C1—C6—H6B109.6C21—C16—C17118.53 (13)
C5—C6—H6B109.6C21—C16—C3120.10 (12)
H6A—C6—H6B108.1C17—C16—C3121.31 (11)
O21—C7—O22124.68 (13)C18—C17—C16120.54 (14)
O21—C7—C2124.59 (12)C18—C17—H17119.7
O22—C7—C2110.69 (11)C16—C17—H17119.7
O22—C8—C9109.62 (14)C19—C18—C17120.62 (16)
O22—C8—C10104.58 (15)C19—C18—H18119.7
C9—C8—C10113.10 (16)C17—C18—H18119.7
O22—C8—H8109.8C18—C19—C20119.37 (14)
C9—C8—H8109.8C18—C19—H19120.3
C10—C8—H8109.8C20—C19—H19120.3
C8—C9—H91109.5C19—C20—C21120.62 (15)
C8—C9—H92109.5C19—C20—H20119.7
H91—C9—H92109.5C21—C20—H20119.7
C8—C9—H93109.5C16—C21—C20120.32 (14)
H91—C9—H93109.5C16—C21—H21119.8
H92—C9—H93109.5C20—C21—H21119.8
C8—C10—H101109.5C7—O22—C8117.99 (12)
C8—C10—H102109.5C5—O51—H51109.5
H101—C10—H102109.5C11—O42—C12118.02 (11)
O11—C1—C2—C70.03 (19)C3—C2—C7—O22150.50 (11)
C6—C1—C2—C7178.36 (11)C3—C4—C11—O4167.57 (16)
O11—C1—C2—C3123.45 (15)C5—C4—C11—O4155.50 (16)
C6—C1—C2—C354.89 (15)C3—C4—C11—O42112.90 (12)
C7—C2—C3—C1662.69 (14)C5—C4—C11—O42124.03 (12)
C1—C2—C3—C16176.05 (11)C2—C3—C16—C21119.98 (13)
C7—C2—C3—C4172.92 (10)C4—C3—C16—C21115.94 (13)
C1—C2—C3—C451.66 (14)C2—C3—C16—C1762.89 (16)
C16—C3—C4—C1158.78 (13)C4—C3—C16—C1761.19 (16)
C2—C3—C4—C11176.00 (10)C21—C16—C17—C180.5 (2)
C16—C3—C4—C5179.96 (10)C3—C16—C17—C18176.65 (13)
C2—C3—C4—C554.75 (13)C16—C17—C18—C190.1 (3)
C11—C4—C5—O5162.42 (13)C17—C18—C19—C200.4 (3)
C3—C4—C5—O5158.10 (14)C18—C19—C20—C210.4 (3)
C11—C4—C5—C1559.68 (15)C17—C16—C21—C200.5 (2)
C3—C4—C5—C15179.80 (11)C3—C16—C21—C20176.71 (13)
C11—C4—C5—C6177.33 (11)C19—C20—C21—C160.0 (2)
C3—C4—C5—C656.81 (14)O21—C7—O22—C84.3 (2)
O11—C1—C6—C5120.75 (16)C2—C7—O22—C8173.81 (12)
C2—C1—C6—C557.55 (15)C9—C8—O22—C776.70 (18)
O51—C5—C6—C161.73 (14)C10—C8—O22—C7161.75 (14)
C15—C5—C6—C1179.52 (12)O41—C11—O42—C123.8 (2)
C4—C5—C6—C156.38 (14)C4—C11—O42—C12176.71 (12)
C1—C2—C7—O2190.69 (16)C13—C12—O42—C11139.02 (15)
C3—C2—C7—O2131.41 (18)C14—C12—O42—C1198.45 (18)
C1—C2—C7—O2287.39 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O21i0.982.603.4678 (16)148
C17—H17···O21i0.932.573.4759 (18)166
C15—H152···O51i0.962.593.404 (2)143
C19—H19···O51ii0.932.553.4005 (18)152
O51—H51···O410.822.082.7724 (14)142
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z1/2.
 

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