1,4,11,12-Tetra­hydro-9,10-anthraquinone

In the title compound, C₁₄H₁₂O₂, the cyclo­hexene ring adopts an envelope conformation, while the remaining fragment of the anthraquinone skeleton is planar.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.138
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.16

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,4,11,12-Tetrahydro-9,10-anthraquinone

Crystal data

C14H12O2	Z = 2
Mr = 212.24	F(000) = 224
Triclinic, P1	Dx = 1.341 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0708 (3) Å	Cell parameters from 2887 reflections
b = 9.6094 (6) Å	θ = 2.3–32.5°
c = 11.9258 (8) Å	µ = 0.09 mm^−1
α = 66.348 (1)°	T = 296 K
β = 86.081 (1)°	Block, colourless
γ = 80.935 (2)°	0.25 × 0.25 × 0.25 mm
V = 525.64 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2143 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Bruker AXS SMART 1000/P4	Rint = 0.013
Graphite monochromator	θmax = 30.0°, θmin = 1.9°
φ and ω scans	h = −6→7
5145 measured reflections	k = −13→13
3052 independent reflections	l = −16→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	All H-atom parameters refined
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0864P)^2] where P = (Fo^2 + 2Fc^2)/3
3052 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

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
C1	1.3113 (3)	−0.39455 (14)	0.35228 (14)	0.0691 (4)
C2	1.0940 (3)	−0.31835 (13)	0.39046 (12)	0.0602 (3)
C3	0.9984 (2)	−0.16618 (11)	0.31757 (10)	0.0446 (2)
C4	0.7663 (2)	−0.08529 (12)	0.36164 (10)	0.0472 (3)
O1	0.63271 (19)	−0.15383 (10)	0.44852 (8)	0.0690 (3)
C5	0.7177 (2)	0.08694 (12)	0.29473 (10)	0.0470 (3)
C6	0.9046 (3)	0.15738 (13)	0.34587 (11)	0.0518 (3)
C7	0.9327 (3)	0.31900 (14)	0.26214 (14)	0.0645 (4)
C8	0.8398 (3)	0.38676 (14)	0.14960 (13)	0.0672 (4)
C9	0.7004 (3)	0.31011 (14)	0.09005 (14)	0.0636 (3)
C10	0.7549 (2)	0.13634 (12)	0.15606 (10)	0.0472 (3)
C11	1.0275 (2)	0.07056 (12)	0.12575 (9)	0.0429 (2)
O2	1.15715 (17)	0.14142 (9)	0.03838 (7)	0.0620 (3)
C12	1.1246 (2)	−0.09148 (11)	0.20682 (9)	0.0421 (2)
C13	1.3455 (2)	−0.17008 (14)	0.17014 (12)	0.0536 (3)
C14	1.4354 (3)	−0.32061 (15)	0.24294 (14)	0.0668 (4)
H1	1.365 (3)	−0.4990 (19)	0.4045 (15)	0.086 (5)*
H2	1.003 (3)	−0.3685 (16)	0.4690 (14)	0.069 (4)*
H5	0.535 (3)	0.1195 (14)	0.3164 (12)	0.057 (3)*
H6A	1.088 (3)	0.0923 (15)	0.3659 (12)	0.066 (4)*
H6B	0.840 (3)	0.1504 (15)	0.4249 (14)	0.065 (4)*
H7	1.032 (3)	0.3704 (18)	0.2978 (15)	0.089 (5)*
H8	0.862 (3)	0.4920 (17)	0.1004 (15)	0.078 (4)*
H9A	0.762 (3)	0.3391 (16)	0.0012 (14)	0.068 (4)*
H9B	0.498 (4)	0.3436 (19)	0.0909 (15)	0.096 (5)*
H10	0.630 (3)	0.0919 (13)	0.1267 (12)	0.056 (3)*
H13	1.436 (3)	−0.1155 (14)	0.0941 (13)	0.058 (4)*
H14	1.581 (3)	−0.3708 (19)	0.2131 (16)	0.090 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0879 (10)	0.0446 (6)	0.0740 (9)	0.0059 (6)	−0.0141 (8)	−0.0261 (6)
C2	0.0790 (9)	0.0446 (6)	0.0543 (7)	−0.0124 (6)	0.0025 (6)	−0.0160 (5)
C3	0.0483 (6)	0.0428 (5)	0.0452 (6)	−0.0101 (4)	0.0030 (5)	−0.0192 (4)
C4	0.0461 (6)	0.0538 (6)	0.0455 (6)	−0.0175 (4)	0.0111 (5)	−0.0214 (5)
O1	0.0754 (6)	0.0682 (5)	0.0641 (6)	−0.0296 (5)	0.0311 (5)	−0.0248 (4)
C5	0.0359 (5)	0.0500 (5)	0.0537 (6)	−0.0056 (4)	0.0119 (5)	−0.0213 (5)
C6	0.0550 (7)	0.0532 (6)	0.0519 (6)	−0.0088 (5)	0.0102 (5)	−0.0269 (5)
C7	0.0775 (9)	0.0555 (7)	0.0723 (9)	−0.0200 (6)	0.0201 (7)	−0.0371 (7)
C8	0.0827 (9)	0.0432 (6)	0.0684 (9)	−0.0043 (6)	0.0206 (7)	−0.0194 (6)
C9	0.0580 (8)	0.0525 (6)	0.0644 (8)	0.0055 (5)	−0.0020 (6)	−0.0114 (6)
C10	0.0383 (5)	0.0500 (5)	0.0501 (6)	−0.0043 (4)	−0.0019 (4)	−0.0168 (5)
C11	0.0416 (5)	0.0507 (5)	0.0372 (5)	−0.0088 (4)	0.0015 (4)	−0.0176 (4)
O2	0.0604 (5)	0.0644 (5)	0.0489 (5)	−0.0093 (4)	0.0143 (4)	−0.0119 (4)
C12	0.0413 (5)	0.0471 (5)	0.0422 (5)	−0.0067 (4)	0.0013 (4)	−0.0224 (4)
C13	0.0539 (6)	0.0603 (6)	0.0537 (7)	−0.0035 (5)	0.0057 (5)	−0.0327 (5)
C14	0.0679 (8)	0.0619 (7)	0.0793 (9)	0.0101 (6)	−0.0049 (7)	−0.0433 (7)

Geometric parameters (Å, º)

C1—C14	1.374 (2)	C7—C8	1.318 (2)
C1—C2	1.379 (2)	C7—H7	0.976 (18)
C1—H1	0.951 (16)	C8—C9	1.483 (2)
C2—C3	1.3941 (15)	C8—H8	0.964 (15)
C2—H2	0.986 (15)	C9—C10	1.5212 (16)
C3—C12	1.3921 (14)	C9—H9A	1.021 (15)
C3—C4	1.4901 (15)	C9—H9B	1.029 (18)
C4—O1	1.2097 (12)	C10—C11	1.5100 (15)
C4—C5	1.5084 (15)	C10—H10	0.973 (13)
C5—C6	1.5299 (16)	C11—O2	1.2081 (12)
C5—C10	1.5335 (16)	C11—C12	1.4891 (14)
C5—H5	0.982 (13)	C12—C13	1.3957 (14)
C6—C7	1.4952 (17)	C13—C14	1.3758 (18)
C6—H6A	1.021 (14)	C13—H13	0.971 (14)
C6—H6B	0.956 (15)	C14—H14	0.945 (18)
C14—C1—C2	120.21 (12)	C7—C8—C9	123.83 (12)
C14—C1—H1	123.3 (10)	C7—C8—H8	120.3 (10)
C2—C1—H1	116.5 (10)	C9—C8—H8	115.9 (10)
C1—C2—C3	120.02 (12)	C8—C9—C10	111.34 (11)
C1—C2—H2	121.7 (8)	C8—C9—H9A	110.5 (8)
C3—C2—H2	118.2 (8)	C10—C9—H9A	108.3 (8)
C12—C3—C2	119.66 (10)	C8—C9—H9B	110.0 (10)
C12—C3—C4	121.23 (9)	C10—C9—H9B	108.2 (9)
C2—C3—C4	119.09 (10)	H9A—C9—H9B	108.4 (13)
O1—C4—C3	121.63 (10)	C11—C10—C9	112.31 (10)
O1—C4—C5	122.59 (10)	C11—C10—C5	111.08 (9)
C3—C4—C5	115.72 (9)	C9—C10—C5	110.97 (10)
C4—C5—C6	108.90 (9)	C11—C10—H10	104.9 (7)
C4—C5—C10	111.75 (9)	C9—C10—H10	108.5 (7)
C6—C5—C10	111.23 (9)	C5—C10—H10	108.8 (7)
C4—C5—H5	105.8 (7)	O2—C11—C12	121.10 (9)
C6—C5—H5	106.9 (7)	O2—C11—C10	122.81 (9)
C10—C5—H5	112.0 (8)	C12—C11—C10	116.03 (9)
C7—C6—C5	112.48 (11)	C3—C12—C13	119.51 (10)
C7—C6—H6A	110.1 (8)	C3—C12—C11	121.39 (9)
C5—C6—H6A	111.7 (7)	C13—C12—C11	119.10 (10)
C7—C6—H6B	111.7 (8)	C14—C13—C12	119.91 (12)
C5—C6—H6B	108.4 (9)	C14—C13—H13	121.4 (7)
H6A—C6—H6B	102.0 (11)	C12—C13—H13	118.6 (7)
C8—C7—C6	124.14 (12)	C1—C14—C13	120.68 (11)
C8—C7—H7	122.2 (10)	C1—C14—H14	122.1 (10)
C6—C7—H7	113.6 (10)	C13—C14—H14	117.2 (10)