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In the title compound, C22H20, the central cyclo­hexene ring is in a slightly distorted half-chair conformation and the structure is stabilized by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047696/sj2163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047696/sj2163Isup2.hkl
Contains datablock I

CCDC reference: 630478

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.066
  • wR factor = 0.221
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C7 - C8 ... 1.39 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C7 - C12 ... 1.41 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC & PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

1-naphthyl-4-phenylcyclohexene top
Crystal data top
C22H20F(000) = 608
Mr = 284.38Dx = 1.157 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 17.1940 (11) Åθ = 9.9–13.1°
b = 7.4760 (6) ŵ = 0.07 mm1
c = 13.7950 (8) ÅT = 293 K
β = 112.99 (2)°Block, colourless
V = 1632.4 (3) Å30.21 × 0.18 × 0.15 mm
Z = 4
Data collection top
MACH3-Nonius sealed tube
diffractometer
1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω–2θ scansh = 2018
Absorption correction: ψ scan
(North et al., 1968)
k = 18
Tmin = 0.940, Tmax = 0.989l = 016
3495 measured reflections3 standard reflections every 60 min
2866 independent reflections intensity decay: none
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1087P)2 + 0.9808P]
where P = (Fo2 + 2Fc2)/3
2866 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.44 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
C10.0452 (2)1.3199 (5)0.6118 (3)0.0744 (9)
H10.02281.26380.54650.089*
C20.0010 (3)1.4577 (5)0.6328 (3)0.0832 (11)
H20.05071.49270.58200.100*
C30.0319 (3)1.5417 (5)0.7259 (4)0.0832 (12)
H30.00181.63450.73990.100*
C40.1077 (3)1.4899 (5)0.7998 (4)0.0882 (12)
H40.12961.54840.86440.106*
C50.1527 (2)1.3506 (5)0.7796 (3)0.0795 (10)
H50.20441.31610.83080.095*
C60.1213 (2)1.2634 (4)0.6845 (3)0.0639 (8)
C70.1688 (3)1.1106 (5)0.6611 (5)0.1053 (15)
H70.21171.09700.73260.126*
C80.1349 (3)0.9393 (4)0.6518 (5)0.1072 (17)
H8A0.07750.94380.59940.129*
H8B0.13160.90900.71840.129*
C90.17948 (19)0.7897 (4)0.6227 (3)0.0716 (10)
H90.15950.67310.61810.086*
C100.25114 (16)0.8269 (3)0.6027 (2)0.0474 (6)
C110.2774 (2)1.0056 (4)0.5980 (3)0.0723 (9)
H11A0.28131.02190.53030.087*
H11B0.33401.01910.65160.087*
C120.2244 (3)1.1543 (4)0.6120 (4)0.1042 (16)
H12A0.26191.24800.65280.125*
H12B0.19121.20370.54310.125*
C130.30257 (16)0.6788 (3)0.5858 (2)0.0472 (6)
C140.3040 (2)0.6495 (4)0.4883 (2)0.0625 (8)
H140.27100.72070.43200.075*
C150.3540 (2)0.5155 (5)0.4715 (2)0.0693 (9)
H150.35340.49850.40440.083*
C160.40338 (19)0.4096 (4)0.5519 (2)0.0614 (8)
H160.43670.32140.53970.074*
C170.40439 (16)0.4329 (3)0.6539 (2)0.0485 (7)
C180.45565 (18)0.3260 (4)0.7394 (2)0.0625 (8)
H180.48890.23700.72810.075*
C190.4573 (2)0.3505 (5)0.8377 (3)0.0692 (9)
H190.49140.27850.89300.083*
C200.4079 (2)0.4835 (5)0.8555 (2)0.0661 (8)
H200.40940.49990.92310.079*
C210.35741 (17)0.5898 (4)0.7759 (2)0.0515 (7)
H210.32480.67750.78970.062*
C220.35386 (15)0.5688 (3)0.67203 (19)0.0430 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.102 (3)0.064 (2)0.069 (2)0.0066 (19)0.0462 (19)0.0023 (17)
C20.097 (3)0.068 (2)0.098 (3)0.027 (2)0.053 (2)0.025 (2)
C30.114 (3)0.0516 (19)0.123 (3)0.007 (2)0.089 (3)0.002 (2)
C40.118 (3)0.072 (2)0.099 (3)0.023 (2)0.069 (3)0.027 (2)
C50.074 (2)0.074 (2)0.092 (3)0.0063 (18)0.0343 (19)0.002 (2)
C60.0722 (19)0.0448 (16)0.092 (2)0.0026 (15)0.0513 (19)0.0047 (16)
C70.114 (3)0.052 (2)0.196 (5)0.004 (2)0.111 (3)0.011 (2)
C80.104 (3)0.0427 (19)0.225 (5)0.0035 (18)0.119 (3)0.003 (2)
C90.0699 (19)0.0387 (15)0.127 (3)0.0000 (14)0.060 (2)0.0017 (17)
C100.0514 (14)0.0412 (14)0.0509 (14)0.0025 (12)0.0213 (12)0.0015 (12)
C110.072 (2)0.0498 (17)0.115 (3)0.0058 (15)0.058 (2)0.0102 (18)
C120.125 (3)0.0403 (18)0.207 (5)0.0034 (19)0.129 (4)0.002 (2)
C130.0498 (14)0.0421 (14)0.0511 (14)0.0017 (12)0.0212 (12)0.0025 (12)
C140.0729 (19)0.0648 (19)0.0495 (16)0.0116 (15)0.0237 (14)0.0013 (14)
C150.085 (2)0.076 (2)0.0535 (17)0.0053 (18)0.0341 (17)0.0119 (16)
C160.0660 (18)0.0562 (17)0.0682 (19)0.0057 (15)0.0331 (16)0.0144 (15)
C170.0460 (14)0.0418 (14)0.0591 (16)0.0015 (11)0.0220 (12)0.0048 (12)
C180.0554 (16)0.0547 (17)0.078 (2)0.0116 (14)0.0267 (15)0.0047 (16)
C190.0663 (19)0.072 (2)0.0645 (19)0.0131 (16)0.0199 (15)0.0188 (17)
C200.0713 (19)0.079 (2)0.0498 (16)0.0009 (17)0.0251 (15)0.0072 (16)
C210.0539 (15)0.0524 (16)0.0544 (16)0.0012 (13)0.0278 (13)0.0030 (13)
C220.0424 (13)0.0376 (13)0.0499 (14)0.0053 (10)0.0191 (11)0.0039 (11)
Geometric parameters (Å, º) top
C1—C61.367 (5)C11—H11A0.9700
C1—C21.377 (5)C11—H11B0.9700
C1—H10.9300C12—H12A0.9700
C2—C31.339 (6)C12—H12B0.9700
C2—H20.9300C13—C141.373 (4)
C3—C41.359 (6)C13—C221.432 (4)
C3—H30.9300C14—C151.396 (4)
C4—C51.389 (5)C14—H140.9300
C4—H40.9300C15—C161.357 (4)
C5—C61.373 (5)C15—H150.9300
C5—H50.9300C16—C171.412 (4)
C6—C71.511 (4)C16—H160.9300
C7—C81.391 (5)C17—C181.412 (4)
C7—C121.409 (5)C17—C221.421 (3)
C7—H70.9800C18—C191.357 (4)
C8—C91.496 (4)C18—H180.9300
C8—H8A0.9700C19—C201.392 (4)
C8—H8B0.9700C19—H190.9300
C9—C101.392 (4)C20—C211.358 (4)
C9—H90.9300C20—H200.9300
C10—C111.420 (4)C21—C221.419 (4)
C10—C131.491 (3)C21—H210.9300
C11—C121.497 (4)
C6—C1—C2121.6 (3)C10—C11—H11B107.8
C6—C1—H1119.2C12—C11—H11B107.8
C2—C1—H1119.2H11A—C11—H11B107.1
C3—C2—C1120.6 (4)C7—C12—C11116.8 (3)
C3—C2—H2119.7C7—C12—H12A108.1
C1—C2—H2119.7C11—C12—H12A108.1
C2—C3—C4119.4 (3)C7—C12—H12B108.1
C2—C3—H3120.3C11—C12—H12B108.1
C4—C3—H3120.3H12A—C12—H12B107.3
C3—C4—C5120.6 (4)C14—C13—C22118.8 (2)
C3—C4—H4119.7C14—C13—C10120.7 (2)
C5—C4—H4119.7C22—C13—C10120.5 (2)
C6—C5—C4120.4 (4)C13—C14—C15121.6 (3)
C6—C5—H5119.8C13—C14—H14119.2
C4—C5—H5119.8C15—C14—H14119.2
C1—C6—C5117.5 (3)C16—C15—C14120.9 (3)
C1—C6—C7121.2 (4)C16—C15—H15119.6
C5—C6—C7121.3 (4)C14—C15—H15119.6
C8—C7—C12120.5 (3)C15—C16—C17120.1 (3)
C8—C7—C6118.3 (3)C15—C16—H16119.9
C12—C7—C6116.9 (3)C17—C16—H16119.9
C8—C7—H797.0C16—C17—C18121.6 (3)
C12—C7—H797.0C16—C17—C22119.6 (2)
C6—C7—H797.0C18—C17—C22118.9 (2)
C7—C8—C9118.2 (3)C19—C18—C17121.4 (3)
C7—C8—H8A107.8C19—C18—H18119.3
C9—C8—H8A107.8C17—C18—H18119.3
C7—C8—H8B107.8C18—C19—C20119.8 (3)
C9—C8—H8B107.8C18—C19—H19120.1
H8A—C8—H8B107.1C20—C19—H19120.1
C10—C9—C8119.3 (3)C21—C20—C19121.1 (3)
C10—C9—H9120.3C21—C20—H20119.4
C8—C9—H9120.3C19—C20—H20119.4
C9—C10—C11121.2 (2)C20—C21—C22120.9 (3)
C9—C10—C13120.5 (2)C20—C21—H21119.5
C11—C10—C13118.2 (2)C22—C21—H21119.5
C10—C11—C12118.2 (3)C21—C22—C17117.9 (2)
C10—C11—H11A107.8C21—C22—C13123.0 (2)
C12—C11—H11A107.8C17—C22—C13119.0 (2)
C6—C1—C2—C30.4 (5)C9—C10—C13—C2271.8 (4)
C1—C2—C3—C40.1 (5)C11—C10—C13—C22108.0 (3)
C2—C3—C4—C50.4 (5)C22—C13—C14—C150.2 (4)
C3—C4—C5—C60.2 (5)C10—C13—C14—C15177.8 (3)
C2—C1—C6—C50.6 (5)C13—C14—C15—C160.3 (5)
C2—C1—C6—C7179.2 (3)C14—C15—C16—C170.5 (5)
C4—C5—C6—C10.3 (5)C15—C16—C17—C18179.4 (3)
C4—C5—C6—C7179.5 (3)C15—C16—C17—C220.5 (4)
C1—C6—C7—C868.6 (6)C16—C17—C18—C19179.1 (3)
C5—C6—C7—C8111.3 (5)C22—C17—C18—C190.1 (4)
C1—C6—C7—C1288.1 (5)C17—C18—C19—C200.1 (5)
C5—C6—C7—C1292.0 (6)C18—C19—C20—C210.2 (5)
C12—C7—C8—C920.9 (8)C19—C20—C21—C220.3 (5)
C6—C7—C8—C9176.7 (4)C20—C21—C22—C170.3 (4)
C7—C8—C9—C102.1 (7)C20—C21—C22—C13179.2 (3)
C8—C9—C10—C117.0 (5)C16—C17—C22—C21179.2 (2)
C8—C9—C10—C13172.9 (3)C18—C17—C22—C210.2 (4)
C9—C10—C11—C121.8 (5)C16—C17—C22—C130.3 (4)
C13—C10—C11—C12178.3 (3)C18—C17—C22—C13179.3 (2)
C8—C7—C12—C1129.4 (7)C14—C13—C22—C21179.3 (3)
C6—C7—C12—C11174.4 (4)C10—C13—C22—C211.6 (4)
C10—C11—C12—C719.6 (6)C14—C13—C22—C170.1 (4)
C9—C10—C13—C14110.5 (3)C10—C13—C22—C17177.8 (2)
C11—C10—C13—C1469.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.932.693.616 (4)176
C9—H9···Cg1ii0.932.983.787 (5)146
C12—H12A···Cg4iii0.972.813.746 (3)163
C18—H18···Cg4iv0.932.713.616 (4)166
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1, z; (iii) x, y1, z; (iv) x+1, y+1/2, z+1/2.
 

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