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The conformation of (-)-membrenone-C, (2S,2'R,3S,3'S)-(1S)-2,2'-ethane-1,1-diyl­bis(6-ethyl-3,5-di­methyl-2,3-di­hydro-4H-pyran-4-one), C20H30O4, in the solid state is found to be the same as that predicted in solution by 1H NMR spectros­copy and nOe (nuclear Overhauser effect) correlations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024796/dn6104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024796/dn6104Isup2.hkl
Contains datablock I

CCDC reference: 227782

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.079
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C4 = 5.08 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11
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 27.70 From the CIF: _reflns_number_total 2294 Count of symmetry unique reflns 2463 Completeness (_total/calc) 93.14% 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 3 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 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999) and Xtal3.7 ADDREF SORTRF (Hall et al., 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: Xtal3.7 CRYLSQ; molecular graphics: Xtal3.7; software used to prepare material for publication: Xtal3.7 BONDLA CIFIO.

(2S,2'R,3S,3'S)-(1S)-2,2'-ethane-1,1-diylbis(6-ethyl-3,5-dimethyl-2,3-dihydro- 4H-pyran-4-one) top
Crystal data top
C20H30O4F(000) = 728
Mr = 334.46Dx = 1.201 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p_2ac_2abCell parameters from 3123 reflections
a = 9.836 (3) Åθ = 2.6–25.1°
b = 13.065 (4) ŵ = 0.08 mm1
c = 14.391 (4) ÅT = 123 K
V = 1849.3 (10) Å3Needle, colourless
Z = 40.75 × 0.12 × 0.11 mm
Data collection top
Bruker P4 CCD area-detector
diffractometer
1648 reflections with F2 > 2σ(F2)
Radiation source: sealed tubeRint = 0.07
Graphite monochromatorθmax = 27.7°
ω scansh = 1212
12757 measured reflectionsk = 1617
2294 independent reflectionsl = 186
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.02Fo2)2]1/2
wR(F2) = 0.079(Δ/σ)max = 0.0003
S = 1.20Δρmax = 0.26 e Å3
2177 reflectionsΔρmin = 0.33 e Å3
217 parameters
Special details top

Experimental. A 1 mm diameter collimator was used.

Refinement. Refinement of F2 against reflections with F2>0. 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 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement Friedel related data were averaged because an attempt to refine a Flack parameter was unsuccessful.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7737 (3)0.97960 (17)0.70830 (14)0.0241 (13)
C20.7805 (3)1.08753 (18)0.66693 (14)0.0229 (13)
C2'0.7483 (3)0.89901 (17)0.63256 (14)0.0226 (13)
C30.7927 (2)1.17478 (18)0.73629 (14)0.0248 (14)
C3'0.6243 (3)0.91530 (17)0.57182 (13)0.0221 (13)
C40.8026 (3)1.2748 (2)0.68225 (15)0.0255 (14)
C4'0.6040 (3)0.82316 (19)0.50883 (14)0.0260 (14)
C50.8773 (3)1.26960 (18)0.59387 (14)0.0239 (14)
C5'0.6524 (3)0.72541 (19)0.54290 (14)0.0252 (14)
C60.9264 (2)1.17911 (19)0.56446 (13)0.0244 (14)
C6'0.7073 (3)0.71902 (19)0.62872 (15)0.0247 (14)
C70.6755 (3)1.1768 (2)0.80563 (15)0.0348 (16)
C7'0.4931 (3)0.93527 (19)0.62545 (15)0.0306 (15)
C80.9024 (3)1.36845 (18)0.54250 (16)0.0349 (16)
C8'0.6251 (3)0.63131 (19)0.48516 (16)0.0360 (16)
C91.0178 (3)1.16186 (19)0.48291 (15)0.0300 (15)
C9'0.7450 (3)0.62110 (17)0.67683 (15)0.0305 (15)
C100.9428 (3)1.1174 (2)0.39987 (16)0.0407 (17)
C10'0.7649 (3)0.62845 (18)0.78042 (17)0.0388 (16)
C110.8992 (3)0.95350 (18)0.76603 (15)0.0315 (15)
O10.89603 (17)1.08727 (12)0.60472 (9)0.0239 (9)
O1'0.73589 (17)0.80256 (11)0.68176 (9)0.0246 (9)
O40.7559 (2)1.35533 (12)0.71207 (11)0.0355 (11)
O4'0.54170 (18)0.83307 (14)0.43506 (10)0.0369 (11)
H20.696341.101260.637040.02900*
H2'0.821890.901750.589800.02900*
H30.872521.165170.772580.03200*
H3'0.642840.975380.536900.02800*
H7a0.687551.232570.847260.05200*
H7b0.673751.114610.839280.05200*
H7c0.592241.185220.772890.05200*
H7'a0.420320.945090.582910.04600*
H7'b0.503490.995450.662280.04600*
H7'c0.473680.878880.664620.04600*
H9a1.087611.115320.500630.03700*
H9b1.057191.225210.465480.03700*
H9'a0.827330.597000.650370.03800*
H9'b0.674590.572700.665750.03800*
H10a1.004471.107930.349930.06200*
H10b0.872911.163600.381240.06200*
H10c0.903331.053710.416390.06200*
H10'a0.788580.563160.804350.05900*
H10'b0.683280.651440.808680.05900*
H10'c0.836020.675750.793300.05900*
H10.697870.978800.749540.03000*
H11a0.890200.886090.790140.04800*
H11b0.907221.000710.815780.04800*
H11c0.977570.957170.727770.04800*
H8a0.863291.367520.482390.05300*
H8b0.998151.381000.536930.05300*
H8c0.863811.425330.576550.05300*
H8'a0.693040.579240.496190.05200*
H8'b0.626810.646290.419600.05200*
H8'c0.538360.602200.499370.05200*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0325 (16)0.0227 (13)0.0170 (11)0.0013 (12)0.0022 (11)0.0019 (10)
C20.0226 (15)0.0225 (13)0.0234 (12)0.0007 (12)0.0019 (11)0.0026 (10)
C2'0.0284 (15)0.0186 (13)0.0209 (11)0.0030 (12)0.0020 (11)0.0036 (10)
C30.0300 (15)0.0244 (14)0.0200 (11)0.0009 (12)0.0008 (10)0.0015 (11)
C3'0.0281 (15)0.0175 (13)0.0207 (11)0.0034 (12)0.0005 (11)0.0070 (10)
C40.0250 (16)0.0250 (15)0.0265 (12)0.0020 (12)0.0063 (11)0.0001 (11)
C4'0.0250 (15)0.0309 (15)0.0222 (12)0.0059 (13)0.0023 (11)0.0000 (11)
C50.0296 (15)0.0209 (14)0.0213 (11)0.0014 (12)0.0069 (11)0.0020 (10)
C5'0.0274 (16)0.0235 (15)0.0247 (12)0.0045 (12)0.0006 (11)0.0042 (11)
C60.0240 (14)0.0284 (15)0.0208 (12)0.0048 (13)0.0037 (10)0.0024 (11)
C6'0.0234 (15)0.0225 (14)0.0282 (13)0.0031 (12)0.0045 (10)0.0005 (11)
C70.0431 (18)0.0277 (15)0.0335 (14)0.0001 (13)0.0107 (12)0.0012 (13)
C7'0.0302 (16)0.0316 (16)0.0300 (13)0.0005 (13)0.0028 (12)0.0034 (12)
C80.0457 (19)0.0313 (17)0.0276 (13)0.0063 (14)0.0015 (13)0.0007 (11)
C8'0.0419 (19)0.0326 (17)0.0335 (14)0.0065 (14)0.0008 (13)0.0094 (11)
C90.0360 (17)0.0291 (15)0.0250 (12)0.0074 (13)0.0046 (11)0.0016 (11)
C9'0.0342 (17)0.0225 (14)0.0347 (13)0.0014 (13)0.0035 (13)0.0025 (11)
C100.055 (2)0.0424 (18)0.0251 (12)0.0006 (15)0.0001 (13)0.0043 (12)
C10'0.055 (2)0.0273 (15)0.0340 (13)0.0028 (15)0.0055 (14)0.0092 (11)
C110.0410 (18)0.0259 (15)0.0277 (13)0.0002 (13)0.0092 (13)0.0021 (11)
O10.0302 (11)0.0203 (9)0.0213 (8)0.0006 (8)0.0043 (7)0.0018 (7)
O1'0.0355 (11)0.0177 (9)0.0207 (8)0.0001 (8)0.0021 (7)0.0022 (6)
O40.0465 (12)0.0196 (10)0.0402 (10)0.0049 (10)0.0059 (10)0.0036 (8)
O4'0.0452 (12)0.0415 (11)0.0239 (9)0.0006 (10)0.0091 (8)0.0004 (8)
Geometric parameters (Å, º) top
C2—C31.520 (3)C7—H7c0.951
C2—C11.532 (3)C7'—H7'a0.951
C2—O11.447 (3)C7'—H7'b0.954
C2—H20.950C7'—H7'c0.947
C2'—C3'1.516 (3)C8—H8a0.947
C2'—C11.536 (3)C8—H8b0.959
C2'—O1'1.451 (3)C8—H8c0.968
C2'—H2'0.950C8'—H8'a0.967
C3—C41.524 (3)C8'—H8'b0.964
C3—C71.525 (3)C8'—H8'c0.956
C3—H30.952C9—C101.520 (3)
C3'—C4'1.520 (3)C9—H9a0.952
C3'—C7'1.527 (4)C9—H9b0.948
C3'—H3'0.950C9'—C10'1.507 (3)
C4—C51.470 (3)C9'—H9'a0.948
C4—O41.226 (3)C9'—H9'b0.952
C4'—C5'1.448 (3)C10—H10a0.948
C4'—O4'1.233 (3)C10—H10b0.954
C5—C61.346 (3)C10—H10c0.948
C5—C81.508 (3)C10'—H10'a0.949
C5'—C6'1.351 (3)C10'—H10'b0.949
C5'—C8'1.508 (3)C10'—H10'c0.952
C6—C91.495 (3)C1—C111.527 (4)
C6—O11.366 (3)C1—H10.953
C6'—C9'1.501 (3)C11—H11a0.951
C6'—O1'1.361 (3)C11—H11b0.948
C7—H7a0.951C11—H11c0.948
C7—H7b0.946
C3—C2—C1116.01 (17)H7'a—C7'—H7'c109.7
C3—C2—O1110.25 (19)H7'b—C7'—H7'c109.4
C3—C2—H2103.0C5—C8—H8a111.7
C1—C2—O1105.81 (18)C5—C8—H8b110.4
C1—C2—H2108.2C5—C8—H8c110.2
O1—C2—H2113.87H8a—C8—H8b109.0
C3'—C2'—C1116.3 (2)H8a—C8—H8c108.2
C3'—C2'—O1'109.6 (2)H8b—C8—H8c107.2
C3'—C2'—H2'103.53C5'—C8'—H8'a111.1
C1—C2'—O1'105.24 (16)C5'—C8'—H8'b111.8
C1—C2'—H2'108.1C5'—C8'—H8'c111.4
O1'—C2'—H2'114.4H8'a—C8'—H8'b107.0
C2—C3—C4108.24 (17)H8'a—C8'—H8'c107.6
C2—C3—C7112.5 (2)H8'b—C8'—H8'c107.8
C2—C3—H3109.1C6—C9—C10112.5 (2)
C4—C3—C7111.6 (2)C6—C9—H9a108.6
C4—C3—H3109.9C6—C9—H9b108.8
C7—C3—H3105.49C10—C9—H9a108.4
C2'—C3'—C4'109.8 (2)C10—C9—H9b108.9
C2'—C3'—C7'114.40 (17)H9a—C9—H9b109.5
C2'—C3'—H3'105.5C6'—C9'—C10'115.7 (2)
C4'—C3'—C7'109.0 (2)C6'—C9'—H9'a108.0
C4'—C3'—H3'111.36C6'—C9'—H9'b108.0
C7'—C3'—H3'106.8C10'—C9'—H9'a107.9
C3—C4—C5115.7 (2)C10'—C9'—H9'b107.6
C3—C4—O4122.2 (2)H9'a—C9'—H9'b109.5
C5—C4—O4122.0 (2)C9—C10—H10a109.6
C3'—C4'—C5'116.95 (18)C9—C10—H10b109.2
C3'—C4'—O4'119.7 (2)C9—C10—H10c109.7
C5'—C4'—O4'123.2 (2)H10a—C10—H10b109.3
C4—C5—C6119.5 (2)H10a—C10—H10c109.8
C4—C5—C8117.8 (2)H10b—C10—H10c109.3
C6—C5—C8122.6 (2)C9'—C10'—H10'a109.5
C4'—C5'—C6'119.7 (2)C9'—C10'—H10'b109.5
C4'—C5'—C8'118.3 (2)C9'—C10'—H10'c109.2
C6'—C5'—C8'121.6 (2)H10'a—C10'—H10'b109.7
C5—C6—C9126.5 (2)H10'a—C10'—H10'c109.4
C5—C6—O1124.0 (2)H10'b—C10'—H10'c109.4
C9—C6—O1109.4 (2)C2—C1—C2'111.24 (17)
C5'—C6'—C9'125.0 (2)C2—C1—C11112.4 (2)
C5'—C6'—O1'123.1 (2)C2—C1—H1106.6
C9'—C6'—O1'111.95 (18)C2'—C1—C11111.4 (2)
C3—C7—H7a109.3C2'—C1—H1107.9
C3—C7—H7b109.5C11—C1—H1106.95
C3—C7—H7c109.2C1—C11—H11a109.3
H7a—C7—H7b109.8C1—C11—H11b109.4
H7a—C7—H7c109.3C1—C11—H11c109.3
H7b—C7—H7c109.7H11a—C11—H11b109.6
C3'—C7'—H7'a109.5H11a—C11—H11c109.6
C3'—C7'—H7'b109.3H11b—C11—H11c109.8
C3'—C7'—H7'c109.8C2—O1—C6115.63 (17)
H7'a—C7'—H7'b109.1C2'—O1'—C6'116.12 (16)
C1—C2—C3—C4178.2 (2)C3—C4—C5—C62.6 (3)
C1—C2—C3—C758.0 (3)C3—C4—C5—C8173.9 (2)
C1—C2—C3—H358.6O4—C4—C5—C6180.0 (2)
O1—C2—C3—C458.0 (2)O4—C4—C5—C83.5 (4)
O1—C2—C3—C7178.26 (18)C3'—C4'—C5'—C6'2.6 (3)
O1—C2—C3—H361.6C3'—C4'—C5'—C8'175.8 (2)
H2—C2—C3—C463.9O4'—C4'—C5'—C6'173.1 (2)
H2—C2—C3—C759.9O4'—C4'—C5'—C8'0.0 (4)
H2—C2—C3—H3176.6C4—C5—C6—C9172.3 (2)
C3—C2—C1—C2'174.8 (2)C4—C5—C6—O19.5 (4)
C3—C2—C1—C1159.5 (3)C8—C5—C6—C94.0 (4)
C3—C2—C1—H157.4C8—C5—C6—O1174.2 (2)
O1—C2—C1—C2'62.7 (2)C4—C5—C8—H8a120.4
O1—C2—C1—C1163.0 (2)C4—C5—C8—H8b118.2
O1—C2—C1—H1179.94C4—C5—C8—H8c0.0
H2—C2—C1—C2'59.7C6—C5—C8—H8a63.3
H2—C2—C1—C11174.58C6—C5—C8—H8b58.1
H2—C2—C1—H157.7C6—C5—C8—H8c176.4
C3—C2—O1—C649.7 (2)C4'—C5'—C6'—C9'171.9 (2)
C1—C2—O1—C6175.86 (17)C4'—C5'—C6'—O1'8.6 (4)
H2—C2—O1—C665.5C8'—C5'—C6'—C9'1.0 (4)
C1—C2'—C3'—C4'173.15 (19)C8'—C5'—C6'—O1'178.6 (2)
C1—C2'—C3'—C7'50.2 (3)C4'—C5'—C8'—H8'a153.1
C1—C2'—C3'—H3'66.8C4'—C5'—C8'—H8'b33.7
O1'—C2'—C3'—C4'54.0 (2)C4'—C5'—C8'—H8'c87.0
O1'—C2'—C3'—C7'68.9 (2)C6'—C5'—C8'—H8'a33.9
O1'—C2'—C3'—H3'174.05C6'—C5'—C8'—H8'b153.3
H2'—C2'—C3'—C4'68.5C6'—C5'—C8'—H8'c86.0
H2'—C2'—C3'—C7'168.6C5—C6—C9—C10104.1 (3)
H2'—C2'—C3'—H3'51.6C5—C6—C9—H9a135.8
C3'—C2'—C1—C255.0 (3)C5—C6—C9—H9b16.7
C3'—C2'—C1—C11178.7 (2)O1—C6—C9—C1074.3 (2)
C3'—C2'—C1—H161.6O1—C6—C9—H9a45.8
O1'—C2'—C1—C2176.5 (2)O1—C6—C9—H9b164.9
O1'—C2'—C1—C1157.2 (2)C5—C6—O1—C215.2 (3)
O1'—C2'—C1—H159.9C9—C6—O1—C2163.29 (18)
H2'—C2'—C1—C260.8C5'—C6'—C9'—C10'162.5 (3)
H2'—C2'—C1—C1165.4C5'—C6'—C9'—H9'a76.5
H2'—C2'—C1—H1177.5C5'—C6'—C9'—H9'b41.8
C3'—C2'—O1'—C6'51.7 (2)O1'—C6'—C9'—C10'18.0 (3)
C1—C2'—O1'—C6'177.5 (2)O1'—C6'—C9'—H9'a103.1
H2'—C2'—O1'—C6'64.1O1'—C6'—C9'—H9'b138.6
C2—C3—C4—C535.2 (3)C5'—C6'—O1'—C2'20.1 (3)
C2—C3—C4—O4147.5 (2)C9'—C6'—O1'—C2'159.5 (2)
C7—C3—C4—C5159.5 (2)C6—C9—C10—H10a179.8
C7—C3—C4—O423.1 (3)C6—C9—C10—H10b60.2
H3—C3—C4—C583.8C6—C9—C10—H10c59.6
H3—C3—C4—O493.5H9a—C9—C10—H10a60.0
C2—C3—C7—H7a179.9H9a—C9—C10—H10b179.7
C2—C3—C7—H7b59.9H9a—C9—C10—H10c60.6
C2—C3—C7—H7c60.3H9b—C9—C10—H10a59.1
C4—C3—C7—H7a58.0H9b—C9—C10—H10b60.6
C4—C3—C7—H7b178.2H9b—C9—C10—H10c179.7
C4—C3—C7—H7c61.6C6'—C9'—C10'—H10'a179.8
H3—C3—C7—H7a61.3C6'—C9'—C10'—H10'b59.8
H3—C3—C7—H7b58.9C6'—C9'—C10'—H10'c60.0
H3—C3—C7—H7c179.1H9'a—C9'—C10'—H10'a58.8
C2'—C3'—C4'—C5'28.5 (3)H9'a—C9'—C10'—H10'b179.1
C2'—C3'—C4'—O4'155.5 (2)H9'a—C9'—C10'—H10'c61.0
C7'—C3'—C4'—C5'97.5 (2)H9'b—C9'—C10'—H10'a59.3
C7'—C3'—C4'—O4'78.4 (3)H9'b—C9'—C10'—H10'b61.0
H3'—C3'—C4'—C5'145.0H9'b—C9'—C10'—H10'c179.1
H3'—C3'—C4'—O4'39.1C2—C1—C11—H11a179.9
C2'—C3'—C7'—H7'a179.7C2—C1—C11—H11b60.0
C2'—C3'—C7'—H7'b60.1C2—C1—C11—H11c60.2
C2'—C3'—C7'—H7'c59.9C2'—C1—C11—H11a54.4
C4'—C3'—C7'—H7'a57.0C2'—C1—C11—H11b174.4
C4'—C3'—C7'—H7'b176.5C2'—C1—C11—H11c65.4
C4'—C3'—C7'—H7'c63.4H1—C1—C11—H11a63.2
H3'—C3'—C7'—H7'a63.4H1—C1—C11—H11b56.7
H3'—C3'—C7'—H7'b56.1H1—C1—C11—H11c176.9
H3'—C3'—C7'—H7'c176.2
 

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