Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The synthesis of (1SR,2SR,5RS,6RS)-5-ethyl-4-(4-methoxy­phenyl)-2,6-di­methyl-3-cyclo­hexene­carboxyl­ic acid was accompanied by the formation of a by-product shown to differ only by the absence of the 5-ethyl group. That mixture was subjected to an enantiomer resolution process utilizing (-)-menthol and di­cyclo­hexyl­carbodi­imide (DCC), and the expected diastereomers of both compounds were formed along with their anhydrides and an unexpected, but related, compound in both cases. The unexpected compound formed from the substrate lacking the 5-ethyl group was unequiv­ocally identified by X-ray analysis as the title compound, C29H42N2O3, (I), a result that, together with the NMR spectra, similarly identified the corresponding product from the compound possessing the 5-ethyl substituent. The two enantiomers of (I) appear to be disordered and superimposed in the asymmetric unit, differing only in the position of the double bond, a rare phenomenon made possible by the unusual stereochemistry of (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016800/hg6067sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016800/hg6067Isup2.hkl
Contains datablock I

CCDC reference: 248809

Key indicators

  • Single-crystal X-ray study
  • T = 155 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.073
  • wR factor = 0.232
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C3
Alert level C PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C5 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C24 PLAT362_ALERT_2_C Short C(sp3)-C(sp2) Bond C4 - C5 ... 1.41 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 6 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2003).

N,N'-Dicyclohexyl-N-[(1RS,2RS,6SR)-4-(4-methoxyphenyl)-2,6-dimethyl-3- cyclohexene-1-carbonyl]urea top
Crystal data top
C29H42N2O3F(000) = 1016
Mr = 466.65Dx = 1.168 Mg m3
Monoclinic, P21/nMelting point = 534–535 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 15.0059 (3) ÅCell parameters from 9091 reflections
b = 10.4719 (2) Åθ = 2.3–29.2°
c = 16.9266 (3) ŵ = 0.08 mm1
β = 93.547 (1)°T = 155 K
V = 2654.76 (9) Å3Prism, colorless
Z = 40.50 × 0.35 × 0.19 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3507 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
φ and ω scansh = 1717
17643 measured reflectionsk = 1212
4675 independent reflectionsl = 2020
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.1585P)2 + 0.2847P]
where P = (Fo2 + 2Fc2)/3
4675 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.32 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.04040 (11)0.23823 (19)0.33237 (9)0.0574 (5)
O20.22702 (10)0.51170 (15)0.26003 (8)0.0444 (4)
O30.28531 (11)0.40887 (17)0.91034 (9)0.0520 (5)
N10.15485 (11)0.31537 (17)0.26599 (9)0.0371 (4)
N20.30937 (11)0.32926 (18)0.26929 (10)0.0408 (5)
C10.16144 (13)0.3261 (2)0.41322 (12)0.0398 (5)
C20.17717 (15)0.2055 (2)0.46376 (12)0.0410 (5)
C30.2101 (2)0.2385 (3)0.54641 (15)0.0704 (9)
C40.19029 (13)0.3526 (2)0.58292 (12)0.0383 (5)
C50.14551 (18)0.4498 (3)0.53801 (14)0.0604 (7)
C60.10474 (14)0.4239 (2)0.45619 (13)0.0424 (5)
C70.09130 (16)0.5470 (2)0.40950 (14)0.0529 (6)
C80.24044 (19)0.1125 (3)0.42687 (14)0.0601 (7)
C90.11367 (14)0.2911 (2)0.33430 (13)0.0420 (5)
C100.21756 (13)0.3708 (2)0.66812 (12)0.0370 (5)
C110.16804 (14)0.4461 (2)0.71823 (12)0.0405 (5)
C120.19277 (14)0.4559 (2)0.79784 (13)0.0415 (5)
C130.26664 (15)0.3924 (2)0.83071 (12)0.0416 (5)
C140.31787 (15)0.3189 (2)0.78234 (13)0.0431 (5)
C150.29212 (14)0.3097 (2)0.70259 (12)0.0404 (5)
C160.36064 (19)0.3430 (3)0.94548 (16)0.0682 (8)
C170.23299 (13)0.3955 (2)0.26552 (11)0.0368 (5)
C180.10785 (14)0.2857 (2)0.18839 (12)0.0409 (5)
C190.17369 (15)0.2556 (2)0.12637 (13)0.0476 (6)
C200.12490 (18)0.2238 (3)0.04667 (14)0.0587 (7)
C210.06166 (18)0.3295 (3)0.02035 (14)0.0608 (7)
C220.00484 (17)0.3554 (3)0.08266 (15)0.0606 (7)
C230.04337 (16)0.3909 (3)0.16145 (14)0.0529 (6)
C240.39730 (13)0.3889 (2)0.26933 (12)0.0395 (5)
C250.45302 (18)0.3252 (3)0.20933 (18)0.0731 (9)
C260.54506 (19)0.3869 (4)0.2099 (2)0.0880 (12)
C270.59217 (18)0.3798 (3)0.2910 (3)0.0853 (11)
C280.53638 (17)0.4450 (3)0.35186 (17)0.0678 (8)
C290.44327 (17)0.3871 (3)0.35103 (15)0.0615 (7)
H10.22040.36550.40330.048*
H20.11830.16150.46670.049*
H2A0.30650.24550.27190.049*
H30.24630.17810.57540.084*
H5A0.18840.52080.53340.072*
H5B0.09710.48210.56990.072*
H60.04460.38510.46190.051*
H7A0.05390.60550.43830.079*
H7B0.06190.52810.35750.079*
H7C0.14940.58700.40260.079*
H8A0.29800.15440.42090.090*
H8B0.21490.08570.37480.090*
H8C0.24920.03760.46120.090*
H110.11690.49090.69700.049*
H120.15830.50730.83070.050*
H140.36960.27580.80360.052*
H150.32730.25910.66990.048*
H16A0.35320.25100.93670.102*
H16B0.36580.36051.00250.102*
H16C0.41480.37220.92150.102*
H180.07170.20690.19570.049*
H19A0.21130.18220.14430.057*
H19B0.21330.33010.12000.057*
H20A0.16910.21100.00630.070*
H20B0.09110.14330.05150.070*
H21A0.02910.30520.03010.073*
H21B0.09600.40820.01100.073*
H22A0.04180.27840.08960.073*
H22B0.04500.42600.06470.073*
H23A0.07650.47180.15560.064*
H23B0.00080.40410.20180.064*
H240.38860.48020.25320.047*
H25A0.42270.33310.15590.088*
H25B0.45940.23330.22190.088*
H26A0.58130.34280.17120.106*
H26B0.53870.47740.19360.106*
H27A0.65110.42210.29020.102*
H27B0.60210.28930.30590.102*
H28A0.56640.43540.40530.081*
H28B0.53170.53730.33980.081*
H29A0.44770.29780.37010.074*
H29B0.40700.43560.38770.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0483 (10)0.0770 (13)0.0468 (10)0.0215 (9)0.0016 (7)0.0073 (8)
O20.0466 (9)0.0388 (10)0.0483 (9)0.0029 (7)0.0064 (7)0.0032 (7)
O30.0629 (10)0.0551 (10)0.0372 (9)0.0108 (8)0.0030 (7)0.0052 (7)
N10.0359 (9)0.0398 (10)0.0355 (9)0.0042 (7)0.0011 (7)0.0029 (8)
N20.0359 (9)0.0402 (11)0.0462 (10)0.0035 (8)0.0014 (7)0.0031 (8)
C10.0377 (11)0.0447 (13)0.0375 (11)0.0032 (9)0.0060 (9)0.0035 (9)
C20.0466 (12)0.0407 (12)0.0361 (11)0.0010 (10)0.0050 (9)0.0015 (9)
C30.125 (3)0.0434 (15)0.0404 (14)0.0207 (16)0.0129 (14)0.0000 (11)
C40.0368 (11)0.0414 (12)0.0373 (11)0.0019 (9)0.0068 (9)0.0031 (9)
C50.0672 (16)0.0635 (18)0.0490 (14)0.0248 (13)0.0085 (12)0.0095 (12)
C60.0385 (11)0.0472 (14)0.0420 (12)0.0030 (10)0.0062 (9)0.0049 (10)
C70.0511 (14)0.0562 (16)0.0528 (14)0.0111 (11)0.0133 (11)0.0089 (12)
C80.0843 (19)0.0508 (16)0.0467 (14)0.0190 (13)0.0163 (12)0.0075 (11)
C90.0388 (12)0.0452 (13)0.0420 (12)0.0050 (10)0.0028 (9)0.0045 (10)
C100.0358 (11)0.0355 (12)0.0402 (12)0.0023 (9)0.0056 (9)0.0000 (9)
C110.0396 (11)0.0386 (13)0.0433 (12)0.0031 (9)0.0022 (9)0.0023 (9)
C120.0431 (12)0.0386 (12)0.0432 (12)0.0042 (9)0.0065 (9)0.0063 (10)
C130.0477 (12)0.0405 (13)0.0365 (11)0.0015 (10)0.0018 (9)0.0030 (9)
C140.0442 (12)0.0393 (13)0.0455 (12)0.0046 (10)0.0012 (9)0.0003 (10)
C150.0424 (12)0.0390 (13)0.0403 (12)0.0050 (9)0.0072 (9)0.0019 (10)
C160.0789 (19)0.075 (2)0.0494 (15)0.0267 (16)0.0103 (13)0.0035 (13)
C170.0392 (11)0.0409 (13)0.0305 (10)0.0026 (9)0.0041 (8)0.0006 (9)
C180.0432 (12)0.0407 (13)0.0381 (12)0.0067 (9)0.0032 (9)0.0009 (9)
C190.0496 (13)0.0489 (14)0.0439 (13)0.0007 (11)0.0009 (10)0.0020 (10)
C200.0668 (16)0.0678 (18)0.0412 (13)0.0049 (14)0.0010 (11)0.0090 (12)
C210.0678 (17)0.0743 (19)0.0388 (13)0.0081 (14)0.0093 (11)0.0026 (12)
C220.0534 (15)0.0731 (19)0.0532 (15)0.0050 (13)0.0139 (12)0.0065 (13)
C230.0484 (14)0.0639 (17)0.0457 (13)0.0105 (12)0.0032 (10)0.0020 (12)
C240.0348 (11)0.0404 (13)0.0432 (12)0.0040 (9)0.0021 (9)0.0005 (9)
C250.0599 (16)0.085 (2)0.0776 (19)0.0213 (15)0.0268 (14)0.0343 (16)
C260.0579 (18)0.102 (3)0.109 (3)0.0275 (17)0.0443 (18)0.047 (2)
C270.0412 (15)0.0445 (17)0.169 (4)0.0019 (12)0.0005 (18)0.0034 (19)
C280.0520 (15)0.077 (2)0.0722 (18)0.0138 (14)0.0187 (13)0.0128 (15)
C290.0525 (15)0.079 (2)0.0515 (15)0.0134 (13)0.0082 (11)0.0090 (13)
Geometric parameters (Å, º) top
C1—C21.535 (3)C5—H5A0.9900
C2—C31.495 (3)C5—H5B0.9900
C3—C41.386 (3)C3—H30.9500
C4—C51.415 (3)C2—H21.0000
C5—C61.504 (3)C7—H7A0.9800
C1—C61.542 (3)C7—H7B0.9800
C2—C81.521 (3)C7—H7C0.9800
C6—C71.520 (3)C8—H8A0.9800
O1—C91.230 (3)C8—H8B0.9800
O2—C171.223 (3)C8—H8C0.9800
O3—C131.370 (2)C11—H110.9500
O3—C161.423 (3)C12—H120.9500
N1—C91.368 (3)C14—H140.9500
N1—C171.442 (3)C15—H150.9500
N1—C181.485 (3)C16—H16A0.9800
N2—C171.338 (3)C16—H16B0.9800
N2—C241.460 (3)C16—H16C0.9800
C1—C91.521 (3)C18—H181.0000
C4—C101.487 (3)C19—H19A0.9900
C10—C151.386 (3)C19—H19B0.9900
C10—C111.404 (3)C20—H20A0.9900
C11—C121.379 (3)C20—H20B0.9900
C12—C131.380 (3)C21—H21A0.9900
C13—C141.390 (3)C21—H21B0.9900
C14—C151.384 (3)C22—H22A0.9900
C18—C231.517 (3)C22—H22B0.9900
C18—C191.518 (3)C23—H23A0.9900
C19—C201.531 (3)C23—H23B0.9900
C20—C211.507 (4)C24—H241.0000
C21—C221.520 (4)C25—H25A0.9900
C22—C231.523 (3)C25—H25B0.9900
C24—C291.507 (3)C26—H26A0.9900
C24—C251.510 (3)C26—H26B0.9900
C25—C261.524 (4)C27—H27A0.9900
C26—C271.507 (5)C27—H27B0.9900
C27—C281.529 (5)C28—H28A0.9900
C28—C291.522 (3)C28—H28B0.9900
N2—H2A0.8800C29—H29A0.9900
C1—H11.0000C29—H29B0.9900
C6—H61.0000
C1—C2—C3111.22 (19)C2—C8—H8C109.5
C2—C3—C4123.3 (2)H8A—C8—H8C109.5
C3—C4—C5119.2 (2)H8B—C8—H8C109.5
C4—C5—C6121.2 (2)C4—C3—H3118.3
C5—C6—C1110.46 (18)C2—C3—H3118.3
C6—C1—C2110.71 (17)C12—C11—H11119.6
C5—C6—C7111.0 (2)C10—C11—H11119.6
C1—C6—C7112.18 (18)C11—C12—H12119.4
C3—C2—C8110.7 (2)C13—C12—H12119.4
C1—C2—C8112.11 (18)C15—C14—H14120.6
C13—O3—C16117.33 (18)C13—C14—H14120.6
C9—N1—C17121.50 (16)C14—C15—H15118.4
C9—N1—C18119.62 (17)C10—C15—H15118.4
C17—N1—C18117.29 (15)O3—C16—H16A109.5
C17—N2—C24123.33 (19)O3—C16—H16B109.5
C9—C1—C2109.81 (19)H16A—C16—H16B109.5
C9—C1—C6109.29 (17)O3—C16—H16C109.5
C3—C4—C10119.3 (2)H16A—C16—H16C109.5
C5—C4—C10121.5 (2)H16B—C16—H16C109.5
O1—C9—N1120.7 (2)N1—C18—H18107.2
O1—C9—C1120.25 (19)C23—C18—H18107.2
N1—C9—C1118.98 (18)C19—C18—H18107.2
C15—C10—C11116.65 (19)C18—C19—H19A109.4
C15—C10—C4121.06 (19)C20—C19—H19A109.4
C11—C10—C4122.25 (19)C18—C19—H19B109.4
C12—C11—C10120.7 (2)C20—C19—H19B109.4
C11—C12—C13121.3 (2)H19A—C19—H19B108.0
O3—C13—C12116.51 (19)C21—C20—H20A109.4
O3—C13—C14124.2 (2)C19—C20—H20A109.4
C12—C13—C14119.3 (2)C21—C20—H20B109.4
C15—C14—C13118.8 (2)C19—C20—H20B109.4
C14—C15—C10123.22 (19)H20A—C20—H20B108.0
O2—C17—N2125.32 (19)C20—C21—H21A109.5
O2—C17—N1121.57 (19)C22—C21—H21A109.5
N2—C17—N1113.09 (19)C20—C21—H21B109.5
N1—C18—C23111.92 (18)C22—C21—H21B109.5
N1—C18—C19111.18 (17)H21A—C21—H21B108.1
C23—C18—C19111.89 (18)C21—C22—H22A109.5
C18—C19—C20110.99 (19)C23—C22—H22A109.5
C21—C20—C19111.0 (2)C21—C22—H22B109.5
C20—C21—C22110.7 (2)C23—C22—H22B109.5
C21—C22—C23110.7 (2)H22A—C22—H22B108.1
C18—C23—C22110.2 (2)C18—C23—H23A109.6
N2—C24—C29110.93 (17)C22—C23—H23A109.6
N2—C24—C25110.40 (19)C18—C23—H23B109.6
C29—C24—C25111.7 (2)C22—C23—H23B109.6
C24—C25—C26110.4 (2)H23A—C23—H23B108.1
C27—C26—C25111.0 (3)N2—C24—H24107.9
C26—C27—C28110.3 (2)C29—C24—H24107.9
C29—C28—C27110.9 (2)C25—C24—H24107.9
C24—C29—C28111.8 (2)C24—C25—H25A109.6
C17—N2—H2A118.3C26—C25—H25A109.6
C24—N2—H2A118.3C24—C25—H25B109.6
C9—C1—H1109.0C26—C25—H25B109.6
C2—C1—H1109.0H25A—C25—H25B108.1
C6—C1—H1109.0C27—C26—H26A109.4
C5—C6—H6107.7C25—C26—H26A109.4
C7—C6—H6107.7C27—C26—H26B109.4
C1—C6—H6107.7C25—C26—H26B109.4
C4—C5—H5A107.0H26A—C26—H26B108.0
C6—C5—H5A107.0C26—C27—H27A109.6
C4—C5—H5B107.0C28—C27—H27A109.6
C6—C5—H5B107.0C26—C27—H27B109.6
H5A—C5—H5B106.8C28—C27—H27B109.6
C3—C2—H2107.5H27A—C27—H27B108.1
C8—C2—H2107.5C29—C28—H28A109.5
C1—C2—H2107.5C27—C28—H28A109.5
C6—C7—H7A109.5C29—C28—H28B109.5
C6—C7—H7B109.5C27—C28—H28B109.5
H7A—C7—H7B109.5H28A—C28—H28B108.1
C6—C7—H7C109.5C24—C29—H29A109.3
H7A—C7—H7C109.5C28—C29—H29A109.3
H7B—C7—H7C109.5C24—C29—H29B109.3
C2—C8—H8A109.5C28—C29—H29B109.3
C2—C8—H8B109.5H29A—C29—H29B107.9
H8A—C8—H8B109.5
C9—C1—C6—C5174.05 (19)C11—C12—C13—C141.0 (3)
C2—C1—C6—C553.0 (3)O3—C13—C14—C15180.0 (2)
C9—C1—C6—C761.5 (2)C12—C13—C14—C151.2 (3)
C2—C1—C6—C7177.42 (18)C13—C14—C15—C100.2 (3)
C7—C6—C5—C4159.4 (2)C11—C10—C15—C140.9 (3)
C1—C6—C5—C434.3 (3)C4—C10—C15—C14177.0 (2)
C6—C5—C4—C311.0 (4)C24—N2—C17—O21.6 (3)
C6—C5—C4—C10169.8 (2)C24—N2—C17—N1179.74 (16)
C5—C4—C3—C27.5 (4)C9—N1—C17—O285.3 (3)
C10—C4—C3—C2173.2 (2)C18—N1—C17—O280.3 (2)
C4—C3—C2—C8153.1 (3)C9—N1—C17—N296.5 (2)
C4—C3—C2—C127.8 (4)C18—N1—C17—N297.9 (2)
C9—C1—C2—C3170.6 (2)C9—N1—C18—C2382.3 (2)
C6—C1—C2—C349.8 (3)C17—N1—C18—C2383.6 (2)
C9—C1—C2—C864.9 (2)C9—N1—C18—C19151.8 (2)
C6—C1—C2—C8174.35 (19)C17—N1—C18—C1942.3 (3)
C17—N1—C9—O1169.5 (2)N1—C18—C19—C20179.4 (2)
C18—N1—C9—O14.3 (3)C23—C18—C19—C2054.6 (3)
C17—N1—C9—C112.7 (3)C18—C19—C20—C2154.9 (3)
C18—N1—C9—C1177.98 (19)C19—C20—C21—C2256.8 (3)
C2—C1—C9—O158.9 (3)C20—C21—C22—C2358.2 (3)
C6—C1—C9—O162.7 (3)N1—C18—C23—C22178.74 (19)
C2—C1—C9—N1118.9 (2)C19—C18—C23—C2255.7 (3)
C6—C1—C9—N1119.5 (2)C21—C22—C23—C1857.1 (3)
C3—C4—C10—C1529.2 (3)C17—N2—C24—C29104.6 (2)
C5—C4—C10—C15150.0 (2)C17—N2—C24—C25131.0 (2)
C3—C4—C10—C11148.5 (3)N2—C24—C25—C26179.6 (3)
C5—C4—C10—C1132.3 (3)C29—C24—C25—C2655.6 (3)
C15—C10—C11—C121.0 (3)C24—C25—C26—C2757.7 (4)
C4—C10—C11—C12176.76 (19)C25—C26—C27—C2857.9 (4)
C10—C11—C12—C130.1 (3)C26—C27—C28—C2955.9 (3)
C16—O3—C13—C12179.3 (2)N2—C24—C29—C28178.1 (2)
C16—O3—C13—C141.9 (3)C25—C24—C29—C2854.5 (3)
C11—C12—C13—O3179.89 (19)C27—C28—C29—C2454.3 (3)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds