4-tert-Butyl-1-(1-naphth­yl)cyclo­hexene

In the title compound, C₂₀H₂₄, the central cyclo­hexene ring is in a distorted half-chair conformation. The crystal structure is stabilized by weak van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.259
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1     -   C1A     ..       7.16 su
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C1

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.259
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

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
   2 ALERT level B = Potentially serious problem
   7 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
   3 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

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Computing details

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 and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

4-tert-butyl-1-(1-napthyl)cyclohexene

Crystal data

C20H24	F(000) = 1152
Mr = 264.39	Dx = 1.079 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 25 reflections
a = 23.8908 (18) Å	θ = 8.4–12.6°
b = 16.1042 (11) Å	µ = 0.06 mm^−1
c = 8.4622 (6) Å	T = 293 K
V = 3255.8 (4) Å^3	Block, colourless
Z = 8	0.24 × 0.21 × 0.17 mm

Data collection

Nonius MACH3 sealed-tube diffractometer	1197 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
ω–2θ scans	h = −1→28
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
Tmin = 0.972, Tmax = 0.990	l = 0→10
3000 measured reflections	3 standard reflections every 60 min
2850 independent reflections	intensity decay: none

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.259	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1398P)^2 + 0.6525P] where P = (Fo^2 + 2Fc^2)/3
2850 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. ¹H NMR (300 MHz, CDCl₃): δ 8.01 (m, 1H, peri-H), 7.26–7.86 (m, 6H, Ar—H), 5.78 (b, 1H, C═CH), 1.50–2.51 (m, 8H, alicyclic protons), 0.97 [s, 9H, C(CH₃)₃].

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
C1A	0.6210 (2)	0.2124 (3)	0.4244 (5)	0.1160 (18)
H1A1	0.6129	0.2414	0.3279	0.174*
H1A2	0.6571	0.2289	0.4629	0.174*
H1A3	0.5930	0.2257	0.5019	0.174*
C1B	0.6681 (2)	0.0948 (4)	0.2872 (5)	0.136 (2)
H1B1	0.6651	0.1239	0.1886	0.204*
H1B2	0.6664	0.0360	0.2684	0.204*
H1B3	0.7032	0.1082	0.3365	0.204*
C1C	0.5647 (3)	0.1005 (4)	0.3074 (6)	0.141 (2)
H1C1	0.5651	0.0441	0.2709	0.211*
H1C2	0.5604	0.1373	0.2189	0.211*
H1C3	0.5340	0.1082	0.3791	0.211*
C1	0.62077 (19)	0.1201 (2)	0.3940 (4)	0.0788 (12)
C2	0.62171 (17)	0.0715 (2)	0.5523 (4)	0.0712 (11)
H2	0.5898	0.0934	0.6118	0.085*
C3	0.67108 (18)	0.0875 (3)	0.6563 (5)	0.0880 (13)
H3A	0.7044	0.0662	0.6048	0.106*
H3B	0.6757	0.1470	0.6685	0.106*
C4	0.66633 (17)	0.0490 (2)	0.8160 (4)	0.0743 (11)
H4A	0.7033	0.0476	0.8634	0.089*
H4B	0.6430	0.0844	0.8813	0.089*
C5	0.64334 (14)	−0.0344 (2)	0.8193 (4)	0.0616 (10)
C6	0.61768 (18)	−0.0663 (2)	0.6903 (4)	0.0808 (12)
H6	0.6037	−0.1202	0.6956	0.097*
C7	0.6108 (2)	−0.0192 (2)	0.5406 (5)	0.0946 (15)
H7A	0.5729	−0.0273	0.5028	0.114*
H7B	0.6359	−0.0425	0.4623	0.114*
C8	0.65285 (15)	−0.0849 (2)	0.9652 (4)	0.0604 (9)
C9	0.70605 (16)	−0.1011 (2)	1.0144 (4)	0.0741 (11)
H9	0.7358	−0.0794	0.9570	0.089*
C10	0.71750 (19)	−0.1494 (2)	1.1479 (5)	0.0823 (12)
H10	0.7544	−0.1591	1.1773	0.099*
C11	0.6754 (2)	−0.1819 (2)	1.2346 (5)	0.0831 (12)
H11	0.6836	−0.2147	1.3221	0.100*
C12	0.61841 (16)	−0.1663 (2)	1.1925 (4)	0.0644 (10)
C13	0.5742 (2)	−0.1978 (2)	1.2821 (5)	0.0850 (13)
H13	0.5816	−0.2311	1.3694	0.102*
C14	0.5213 (2)	−0.1803 (3)	1.2433 (6)	0.0962 (14)
H14	0.4923	−0.2016	1.3046	0.115*
C15	0.50850 (17)	−0.1305 (3)	1.1119 (5)	0.0850 (12)
H15	0.4713	−0.1191	1.0873	0.102*
C16	0.54985 (17)	−0.0990 (2)	1.0215 (5)	0.0716 (10)
H16	0.5411	−0.0656	0.9354	0.086*
C17	0.60760 (14)	−0.11697 (19)	1.0574 (4)	0.0568 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.179 (5)	0.095 (3)	0.074 (3)	0.020 (3)	−0.002 (3)	0.016 (3)
C1B	0.163 (5)	0.169 (6)	0.077 (3)	0.055 (4)	0.049 (3)	0.034 (3)
C1C	0.176 (6)	0.134 (5)	0.112 (4)	0.003 (4)	−0.075 (4)	0.023 (3)
C1	0.120 (3)	0.070 (2)	0.047 (2)	0.012 (2)	−0.005 (2)	−0.0009 (18)
C2	0.095 (3)	0.070 (2)	0.049 (2)	0.004 (2)	−0.0105 (19)	−0.0020 (17)
C3	0.097 (3)	0.090 (3)	0.077 (3)	−0.016 (2)	−0.020 (2)	0.017 (2)
C4	0.085 (3)	0.081 (3)	0.057 (2)	−0.005 (2)	−0.0141 (19)	0.0013 (19)
C5	0.066 (2)	0.065 (2)	0.054 (2)	0.0004 (17)	−0.0042 (18)	−0.0020 (18)
C6	0.115 (3)	0.062 (2)	0.065 (2)	−0.012 (2)	−0.022 (2)	0.0023 (19)
C7	0.136 (4)	0.077 (3)	0.072 (3)	−0.019 (3)	−0.034 (3)	0.001 (2)
C8	0.071 (2)	0.057 (2)	0.053 (2)	0.0046 (17)	−0.0069 (19)	−0.0063 (17)
C9	0.067 (2)	0.084 (3)	0.071 (2)	0.0146 (19)	−0.012 (2)	−0.005 (2)
C10	0.081 (3)	0.088 (3)	0.077 (3)	0.025 (2)	−0.022 (2)	−0.003 (2)
C11	0.112 (4)	0.066 (3)	0.071 (3)	0.018 (2)	−0.018 (3)	0.001 (2)
C12	0.087 (3)	0.0468 (19)	0.059 (2)	0.0069 (18)	−0.004 (2)	−0.0058 (16)
C13	0.117 (4)	0.064 (3)	0.073 (3)	0.000 (3)	0.012 (3)	0.005 (2)
C14	0.099 (4)	0.088 (3)	0.101 (4)	−0.016 (3)	0.019 (3)	0.002 (3)
C15	0.069 (3)	0.089 (3)	0.097 (3)	−0.012 (2)	0.005 (2)	0.000 (3)
C16	0.076 (3)	0.065 (2)	0.074 (2)	−0.0013 (19)	−0.007 (2)	−0.0032 (19)
C17	0.071 (2)	0.0452 (17)	0.055 (2)	0.0008 (15)	−0.0070 (17)	−0.0083 (15)

Geometric parameters (Å, º)

C1A—C1	1.509 (6)	C5—C8	1.496 (5)
C1A—H1A1	0.9600	C6—C7	1.485 (5)
C1A—H1A2	0.9600	C6—H6	0.9300
C1A—H1A3	0.9600	C7—H7A	0.9700
C1B—C1	1.505 (6)	C7—H7B	0.9700
C1B—H1B1	0.9600	C8—C9	1.363 (5)
C1B—H1B2	0.9600	C8—C17	1.430 (5)
C1B—H1B3	0.9600	C9—C10	1.398 (5)
C1C—C1	1.560 (6)	C9—H9	0.9300
C1C—H1C1	0.9600	C10—C11	1.350 (6)
C1C—H1C2	0.9600	C10—H10	0.9300
C1C—H1C3	0.9600	C11—C12	1.431 (5)
C1—C2	1.551 (5)	C11—H11	0.9300
C2—C7	1.488 (5)	C12—C13	1.395 (5)
C2—C3	1.494 (5)	C12—C17	1.416 (5)
C2—H2	0.9800	C13—C14	1.336 (6)
C3—C4	1.491 (5)	C13—H13	0.9300
C3—H3A	0.9700	C14—C15	1.405 (6)
C3—H3B	0.9700	C14—H14	0.9300
C4—C5	1.451 (5)	C15—C16	1.349 (5)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C17	1.442 (5)
C5—C6	1.353 (5)	C16—H16	0.9300
C1—C1A—H1A1	109.5	C6—C5—C4	120.4 (3)
C1—C1A—H1A2	109.5	C6—C5—C8	121.9 (3)
H1A1—C1A—H1A2	109.5	C4—C5—C8	117.5 (3)
C1—C1A—H1A3	109.5	C5—C6—C7	123.0 (3)
H1A1—C1A—H1A3	109.5	C5—C6—H6	118.5
H1A2—C1A—H1A3	109.5	C7—C6—H6	118.5
C1—C1B—H1B1	109.5	C6—C7—C2	115.2 (3)
C1—C1B—H1B2	109.5	C6—C7—H7A	108.5
H1B1—C1B—H1B2	109.5	C2—C7—H7A	108.5
C1—C1B—H1B3	109.5	C6—C7—H7B	108.5
H1B1—C1B—H1B3	109.5	C2—C7—H7B	108.5
H1B2—C1B—H1B3	109.5	H7A—C7—H7B	107.5
C1—C1C—H1C1	109.5	C9—C8—C17	118.0 (3)
C1—C1C—H1C2	109.5	C9—C8—C5	119.9 (3)
H1C1—C1C—H1C2	109.5	C17—C8—C5	122.1 (3)
C1—C1C—H1C3	109.5	C8—C9—C10	122.4 (4)
H1C1—C1C—H1C3	109.5	C8—C9—H9	118.8
H1C2—C1C—H1C3	109.5	C10—C9—H9	118.8
C1B—C1—C1A	111.5 (4)	C11—C10—C9	120.6 (4)
C1B—C1—C2	111.8 (3)	C11—C10—H10	119.7
C1A—C1—C2	110.4 (3)	C9—C10—H10	119.7
C1B—C1—C1C	108.0 (4)	C10—C11—C12	120.3 (4)
C1A—C1—C1C	106.3 (4)	C10—C11—H11	119.8
C2—C1—C1C	108.5 (4)	C12—C11—H11	119.8
C7—C2—C3	110.2 (3)	C13—C12—C17	120.3 (4)
C7—C2—C1	115.8 (3)	C13—C12—C11	121.4 (4)
C3—C2—C1	115.7 (3)	C17—C12—C11	118.3 (4)
C7—C2—H2	104.5	C14—C13—C12	120.4 (4)
C3—C2—H2	104.5	C14—C13—H13	119.8
C1—C2—H2	104.5	C12—C13—H13	119.8
C4—C3—C2	113.7 (3)	C13—C14—C15	121.4 (4)
C4—C3—H3A	108.8	C13—C14—H14	119.3
C2—C3—H3A	108.8	C15—C14—H14	119.3
C4—C3—H3B	108.8	C16—C15—C14	120.3 (4)
C2—C3—H3B	108.8	C16—C15—H15	119.9
H3A—C3—H3B	107.7	C14—C15—H15	119.9
C5—C4—C3	115.6 (3)	C15—C16—C17	120.4 (4)
C5—C4—H4A	108.4	C15—C16—H16	119.8
C3—C4—H4A	108.4	C17—C16—H16	119.8
C5—C4—H4B	108.4	C12—C17—C8	120.3 (3)
C3—C4—H4B	108.4	C12—C17—C16	117.2 (3)
H4A—C4—H4B	107.5	C8—C17—C16	122.4 (3)
C1B—C1—C2—C7	−66.3 (5)	C5—C8—C9—C10	−178.6 (3)
C1A—C1—C2—C7	168.9 (4)	C8—C9—C10—C11	−0.2 (6)
C1C—C1—C2—C7	52.7 (5)	C9—C10—C11—C12	−1.1 (6)
C1B—C1—C2—C3	64.9 (5)	C10—C11—C12—C13	−178.6 (4)
C1A—C1—C2—C3	−59.9 (5)	C10—C11—C12—C17	0.8 (5)
C1C—C1—C2—C3	−176.1 (4)	C17—C12—C13—C14	−1.4 (6)
C7—C2—C3—C4	−54.3 (5)	C11—C12—C13—C14	178.0 (4)
C1—C2—C3—C4	171.9 (3)	C12—C13—C14—C15	0.3 (7)
C2—C3—C4—C5	41.4 (5)	C13—C14—C15—C16	0.1 (7)
C3—C4—C5—C6	−13.1 (5)	C14—C15—C16—C17	0.7 (6)
C3—C4—C5—C8	162.5 (3)	C13—C12—C17—C8	−179.8 (3)
C4—C5—C6—C7	−0.7 (6)	C11—C12—C17—C8	0.8 (5)
C8—C5—C6—C7	−176.2 (4)	C13—C12—C17—C16	2.1 (5)
C5—C6—C7—C2	−13.8 (6)	C11—C12—C17—C16	−177.3 (3)
C3—C2—C7—C6	40.1 (5)	C9—C8—C17—C12	−2.0 (4)
C1—C2—C7—C6	173.9 (4)	C5—C8—C17—C12	178.4 (3)
C6—C5—C8—C9	116.9 (4)	C9—C8—C17—C16	176.0 (3)
C4—C5—C8—C9	−58.7 (4)	C5—C8—C17—C16	−3.6 (5)
C6—C5—C8—C17	−63.5 (5)	C15—C16—C17—C12	−1.8 (5)
C4—C5—C8—C17	120.9 (4)	C15—C16—C17—C8	−179.8 (3)
C17—C8—C9—C10	1.7 (5)