(4aS*,7aR*)-2,10-Dioxoper­hydro­benzo­[d]­naphthalene

The title racemic compound, C₁₄H₂₀O₂, a tricylic diketone isolated from en­amine reactions of cyclo­hexanone with methyl vinyl ketone, is shown to have an all-chair conformation and a cis stereochemical relationship for its methine H atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.086
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.90
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

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           25.00
           From the CIF: _reflns_number_total               1154
           Count of symmetry unique reflns         1154
           Completeness (_total/calc)            100.00%
           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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(4aS*,7aR*)-2,10(3H,11H)-Dioxooctahydro-1H-benzo[d]naphthalene

Crystal data

C14H20O2	Dx = 1.219 Mg m^−3
Mr = 220.30	Melting point: 435 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 33 reflections
a = 10.618 (3) Å	θ = 2.3–9.9°
b = 16.224 (4) Å	µ = 0.08 mm^−1
c = 6.9661 (15) Å	T = 296 K
V = 1200.0 (5) Å^3	Parallelepiped, colourless
Z = 4	0.50 × 0.19 × 0.19 mm
F(000) = 480

Data collection

Siemens P4 diffractometer	725 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
2θ/θ scans	h = −12→12
Absorption correction: numerical (SHELXTL; Sheldrick, 1997)	k = −19→19
Tmin = 0.975, Tmax = 0.983	l = −8→8
2308 measured reflections	3 standard reflections every 97 reflections
1154 independent reflections	intensity decay: variation <1.2

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0192P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.086	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.13 e Å^−3
1154 reflections	Δρmin = −0.12 e Å^−3
146 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.022 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: see text
Secondary atom site location: difference Fourier map

Special details

Experimental. crystal mounted on glass fiber using cyanoacrylate cement

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
O1	0.4304 (2)	0.53088 (16)	0.6233 (5)	0.0663 (8)
O2	0.5464 (3)	0.7321 (2)	0.2868 (5)	0.1125 (14)
C1	0.6070 (3)	0.6117 (2)	0.7216 (6)	0.0444 (9)
H1A	0.6199	0.6091	0.8593	0.053*
H1B	0.5515	0.6579	0.6955	0.053*
C2	0.5435 (3)	0.5333 (2)	0.6564 (6)	0.0469 (9)
C3	0.6234 (3)	0.4580 (2)	0.6467 (7)	0.0557 (10)
H3A	0.5799	0.4165	0.5715	0.067*
H3B	0.6343	0.4363	0.7754	0.067*
C4A	0.8167 (3)	0.54921 (19)	0.6426 (6)	0.0464 (9)
H4A	0.8929	0.5587	0.5663	0.056*
C4	0.7524 (3)	0.4729 (2)	0.5589 (6)	0.0569 (11)
H4B	0.7435	0.4797	0.4212	0.068*
H4C	0.8052	0.4251	0.5814	0.068*
C5	0.8596 (4)	0.5352 (2)	0.8494 (6)	0.0593 (12)
H5A	0.7867	0.5223	0.9279	0.071*
H5B	0.9158	0.4881	0.8532	0.071*
C6	0.9263 (4)	0.6092 (2)	0.9335 (7)	0.0725 (13)
H6A	0.9445	0.5990	1.0679	0.087*
H6B	1.0058	0.6173	0.8674	0.087*
C7A	0.8059 (3)	0.7014 (2)	0.7101 (5)	0.0507 (11)
H7A	0.8831	0.7080	0.6344	0.061*
C7	0.8474 (4)	0.6864 (3)	0.9155 (6)	0.0625 (13)
H7B	0.8958	0.7334	0.9600	0.075*
H7C	0.7736	0.6814	0.9967	0.075*
C8	0.7323 (4)	0.7811 (2)	0.6884 (7)	0.0695 (14)
H8A	0.7821	0.8264	0.7381	0.083*
H8B	0.6556	0.7777	0.7635	0.083*
C9	0.6985 (5)	0.7984 (3)	0.4772 (7)	0.0836 (17)
H9A	0.6401	0.8444	0.4718	0.100*
H9B	0.7741	0.8142	0.4084	0.100*
C10	0.6412 (5)	0.7265 (3)	0.3817 (6)	0.0690 (14)
C11	0.7093 (4)	0.6468 (2)	0.4094 (5)	0.0581 (11)
H11A	0.7889	0.6491	0.3413	0.070*
H11B	0.6597	0.6026	0.3538	0.070*
C11A	0.7346 (3)	0.62721 (18)	0.6227 (5)	0.0379 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0419 (15)	0.0775 (19)	0.079 (2)	−0.0062 (14)	−0.0077 (16)	0.0066 (19)
O2	0.103 (3)	0.115 (3)	0.119 (3)	0.013 (2)	−0.051 (3)	0.037 (2)
C1	0.0401 (19)	0.0410 (19)	0.052 (2)	0.0018 (18)	0.0025 (18)	0.0011 (18)
C2	0.044 (2)	0.053 (2)	0.044 (2)	−0.0028 (19)	0.000 (2)	0.009 (2)
C3	0.055 (2)	0.044 (2)	0.068 (3)	−0.001 (2)	−0.005 (3)	0.001 (2)
C4A	0.0335 (17)	0.054 (2)	0.052 (2)	0.0029 (18)	0.007 (2)	0.002 (2)
C4	0.054 (2)	0.046 (2)	0.070 (3)	0.012 (2)	0.006 (2)	−0.004 (2)
C5	0.039 (2)	0.064 (3)	0.075 (3)	0.004 (2)	−0.011 (2)	0.014 (2)
C6	0.053 (3)	0.093 (3)	0.071 (3)	−0.005 (3)	−0.022 (2)	0.019 (3)
C7A	0.043 (2)	0.051 (2)	0.058 (3)	−0.006 (2)	0.001 (2)	0.0026 (19)
C7	0.055 (3)	0.076 (3)	0.056 (3)	−0.014 (2)	−0.006 (2)	−0.009 (2)
C8	0.066 (3)	0.044 (2)	0.098 (4)	−0.005 (2)	0.001 (3)	0.002 (2)
C9	0.085 (3)	0.050 (3)	0.116 (5)	0.003 (3)	−0.011 (3)	0.037 (3)
C10	0.073 (3)	0.073 (3)	0.061 (3)	−0.002 (3)	−0.002 (3)	0.038 (3)
C11	0.065 (3)	0.060 (2)	0.050 (2)	−0.003 (2)	−0.002 (2)	0.018 (2)
C11A	0.0330 (18)	0.0412 (18)	0.0393 (19)	0.0029 (16)	0.0005 (18)	0.0061 (18)

Geometric parameters (Å, º)

O1—C2	1.223 (4)	C6—C7	1.513 (5)
O2—C10	1.208 (5)	C6—H6A	0.9700
C1—C2	1.509 (5)	C6—H6B	0.9700
C1—C11A	1.541 (4)	C7A—C7	1.516 (5)
C1—H1A	0.9700	C7A—C8	1.518 (5)
C1—H1B	0.9700	C7A—C11A	1.546 (4)
C2—C3	1.489 (4)	C7A—H7A	0.9800
C3—C4	1.519 (5)	C7—H7B	0.9700
C3—H3A	0.9700	C7—H7C	0.9700
C3—H3B	0.9700	C8—C9	1.540 (6)
C4A—C5	1.528 (6)	C8—H8A	0.9700
C4A—C4	1.530 (5)	C8—H8B	0.9700
C4A—C11A	1.543 (4)	C9—C10	1.474 (6)
C4A—H4A	0.9800	C9—H9A	0.9700
C4—H4B	0.9700	C9—H9B	0.9700
C4—H4C	0.9700	C10—C11	1.494 (6)
C5—C6	1.513 (5)	C11—C11A	1.543 (5)
C5—H5A	0.9700	C11—H11A	0.9700
C5—H5B	0.9700	C11—H11B	0.9700
C2—C1—C11A	113.3 (3)	C7—C7A—C8	112.3 (3)
C2—C1—H1A	108.9	C7—C7A—C11A	112.9 (3)
C11A—C1—H1A	108.9	C8—C7A—C11A	111.8 (3)
C2—C1—H1B	108.9	C7—C7A—H7A	106.4
C11A—C1—H1B	108.9	C8—C7A—H7A	106.4
H1A—C1—H1B	107.7	C11A—C7A—H7A	106.4
O1—C2—C3	121.7 (4)	C6—C7—C7A	111.8 (3)
O1—C2—C1	121.4 (3)	C6—C7—H7B	109.3
C3—C2—C1	116.8 (3)	C7A—C7—H7B	109.3
C2—C3—C4	113.7 (3)	C6—C7—H7C	109.3
C2—C3—H3A	108.8	C7A—C7—H7C	109.3
C4—C3—H3A	108.8	H7B—C7—H7C	107.9
C2—C3—H3B	108.8	C7A—C8—C9	111.8 (3)
C4—C3—H3B	108.8	C7A—C8—H8A	109.3
H3A—C3—H3B	107.7	C9—C8—H8A	109.3
C5—C4A—C4	111.8 (3)	C7A—C8—H8B	109.3
C5—C4A—C11A	112.1 (3)	C9—C8—H8B	109.3
C4—C4A—C11A	112.2 (3)	H8A—C8—H8B	107.9
C5—C4A—H4A	106.8	C10—C9—C8	112.5 (4)
C4—C4A—H4A	106.8	C10—C9—H9A	109.1
C11A—C4A—H4A	106.8	C8—C9—H9A	109.1
C3—C4—C4A	112.2 (3)	C10—C9—H9B	109.1
C3—C4—H4B	109.2	C8—C9—H9B	109.1
C4A—C4—H4B	109.2	H9A—C9—H9B	107.8
C3—C4—H4C	109.2	O2—C10—C9	122.1 (5)
C4A—C4—H4C	109.2	O2—C10—C11	122.6 (5)
H4B—C4—H4C	107.9	C9—C10—C11	115.3 (4)
C6—C5—C4A	112.7 (3)	C10—C11—C11A	112.8 (3)
C6—C5—H5A	109.0	C10—C11—H11A	109.0
C4A—C5—H5A	109.0	C11A—C11—H11A	109.0
C6—C5—H5B	109.0	C10—C11—H11B	109.0
C4A—C5—H5B	109.0	C11A—C11—H11B	109.0
H5A—C5—H5B	107.8	H11A—C11—H11B	107.8
C7—C6—C5	111.4 (3)	C1—C11A—C4A	108.8 (3)
C7—C6—H6A	109.3	C1—C11A—C11	108.1 (3)
C5—C6—H6A	109.3	C4A—C11A—C11	110.7 (3)
C7—C6—H6B	109.3	C1—C11A—C7A	112.5 (3)
C5—C6—H6B	109.3	C4A—C11A—C7A	109.0 (3)
H6A—C6—H6B	108.0	C11—C11A—C7A	107.7 (3)
C11A—C1—C2—O1	−137.5 (4)	C9—C10—C11—C11A	52.4 (5)
C11A—C1—C2—C3	46.3 (5)	C2—C1—C11A—C4A	−51.6 (4)
O1—C2—C3—C4	140.7 (4)	C2—C1—C11A—C11	68.7 (4)
C1—C2—C3—C4	−43.1 (5)	C2—C1—C11A—C7A	−172.5 (3)
C2—C3—C4—C4A	47.0 (5)	C5—C4A—C11A—C1	−69.7 (4)
C5—C4A—C4—C3	71.3 (4)	C4—C4A—C11A—C1	57.1 (4)
C11A—C4A—C4—C3	−55.5 (5)	C5—C4A—C11A—C11	171.6 (3)
C4—C4A—C5—C6	178.6 (3)	C4—C4A—C11A—C11	−61.6 (4)
C11A—C4A—C5—C6	−54.5 (4)	C5—C4A—C11A—C7A	53.3 (4)
C4A—C5—C6—C7	53.7 (5)	C4—C4A—C11A—C7A	−179.9 (3)
C5—C6—C7—C7A	−53.8 (5)	C10—C11—C11A—C1	66.7 (4)
C8—C7A—C7—C6	−177.0 (3)	C10—C11—C11A—C4A	−174.2 (3)
C11A—C7A—C7—C6	55.5 (4)	C10—C11—C11A—C7A	−55.0 (4)
C7—C7A—C8—C9	176.2 (3)	C7—C7A—C11A—C1	66.4 (4)
C11A—C7A—C8—C9	−55.7 (5)	C8—C7A—C11A—C1	−61.4 (4)
C7A—C8—C9—C10	49.4 (5)	C7—C7A—C11A—C4A	−54.4 (4)
C8—C9—C10—O2	132.4 (4)	C8—C7A—C11A—C4A	177.8 (3)
C8—C9—C10—C11	−48.1 (5)	C7—C7A—C11A—C11	−174.6 (3)
O2—C10—C11—C11A	−128.0 (4)	C8—C7A—C11A—C11	57.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1^i	0.97	2.58	3.374 (6)	140

Symmetry code: (i) −x+1, −y+1, z+1/2.