10-(3-Methoxy­benzyl­idene)anthrone

The title compound, C₂₂H₁₆O₂, was prepared from anthrone and 3-methoxy­benzaldehyde in the presence of pyridine. X-ray analysis shows that the anthraquinone ring system is not planar. The central six-membered ring adopts an asymmetric boat conformation, in which the carbonyl C and the para-C atoms deviate from the plane of the other four atoms by 0.162 (8) and 0.267 (8) Å, respectively. Inter­molecular C—H...O hydrogen bonds are present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.053
• wR factor = 0.184
• Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.03
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H16 O2

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           25.16
           From the CIF: _reflns_number_total               1532
           Count of symmetry unique reflns         1534
           Completeness (_total/calc)             99.87%
           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
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (McArdle, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

10-(3-Methoxybenzylidene)anthrone

Crystal data

C22H16O2	F(000) = 656
Mr = 312.35	Dx = 1.269 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 7.165 (2) Å	θ = 10.5–10.8°
b = 16.345 (2) Å	µ = 0.08 mm^−1
c = 13.963 (3) Å	T = 295 K
V = 1635.2 (6) Å^3	Block, yellow
Z = 4	0.40 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	818 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.2°, θmin = 1.9°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −19→1
Tmin = 0.963, Tmax = 0.967	l = 0→16
1647 measured reflections	3 standard reflections every 60 min
1532 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1119P)^2 + 0.1776P] where P = (Fo^2 + 2Fc^2)/3
1532 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

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	0.2024 (7)	0.5993 (3)	0.8681 (3)	0.0791 (14)
O2	0.3646 (6)	0.7201 (4)	1.5608 (3)	0.0939 (17)
C1	0.1785 (9)	0.7696 (5)	0.8860 (5)	0.0678 (17)
H1	0.1823	0.7478	0.8245	0.081*
C2	0.1741 (10)	0.8520 (5)	0.8974 (6)	0.0730 (19)
H2	0.1752	0.8863	0.8442	0.088*
C3	0.1681 (9)	0.8843 (4)	0.9883 (6)	0.0711 (19)
H3	0.1626	0.9407	0.9970	0.085*
C4	0.1702 (8)	0.8329 (4)	1.0666 (4)	0.0562 (15)
H4	0.1672	0.8557	1.1276	0.067*
C5	0.1919 (7)	0.6926 (4)	1.1399 (4)	0.0492 (14)
C6	0.0633 (9)	0.5590 (5)	1.1978 (5)	0.0694 (18)
H6	0.0550	0.5799	1.2596	0.083*
C7	0.0075 (11)	0.4803 (5)	1.1796 (6)	0.087 (2)
H7	−0.0369	0.4482	1.2297	0.105*
C8	0.0158 (12)	0.4477 (4)	1.0882 (7)	0.091 (3)
H8	−0.0187	0.3937	1.0770	0.109*
C9	0.0755 (9)	0.4962 (4)	1.0150 (5)	0.0686 (18)
H9	0.0795	0.4751	0.9531	0.082*
C10	0.1755 (8)	0.6295 (4)	0.9482 (4)	0.0597 (17)
C11	0.1766 (6)	0.7494 (4)	1.0575 (4)	0.0496 (14)
C12	0.1326 (7)	0.6080 (4)	1.1241 (4)	0.0541 (15)
C13	0.1292 (8)	0.5750 (4)	1.0307 (4)	0.0551 (15)
C14	0.1773 (7)	0.7169 (4)	0.9641 (4)	0.0511 (14)
C15	0.2700 (8)	0.7207 (4)	1.2218 (4)	0.0541 (15)
H15	0.2828	0.7773	1.2244	0.065*
C16	0.3382 (8)	0.6778 (4)	1.3074 (4)	0.0528 (14)
C17	0.3196 (9)	0.7137 (4)	1.3965 (4)	0.0622 (15)
H17	0.2548	0.7628	1.4020	0.075*
C18	0.3954 (9)	0.6782 (4)	1.4779 (4)	0.0658 (17)
C19	0.4886 (11)	0.6072 (4)	1.4700 (5)	0.0703 (19)
H19	0.5374	0.5828	1.5247	0.084*
C20	0.5132 (9)	0.5699 (4)	1.3827 (5)	0.0682 (18)
H20	0.5819	0.5217	1.3783	0.082*
C21	0.4353 (8)	0.6042 (4)	1.3012 (5)	0.0609 (16)
H21	0.4479	0.5781	1.2424	0.073*
C22	0.4499 (14)	0.6891 (6)	1.6460 (5)	0.120 (3)
H22A	0.3919	0.6383	1.6635	0.180*
H22B	0.4345	0.7279	1.6970	0.180*
H22C	0.5805	0.6802	1.6347	0.180*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.089 (3)	0.095 (3)	0.053 (3)	0.006 (3)	−0.006 (2)	−0.015 (3)
O2	0.087 (3)	0.149 (5)	0.045 (3)	0.016 (3)	−0.007 (3)	−0.016 (3)
C1	0.059 (4)	0.087 (5)	0.058 (4)	0.006 (4)	0.002 (3)	0.014 (4)
C2	0.060 (4)	0.097 (6)	0.062 (4)	0.004 (4)	0.000 (3)	0.030 (4)
C3	0.060 (4)	0.069 (4)	0.085 (5)	0.002 (3)	−0.004 (3)	0.022 (4)
C4	0.051 (3)	0.062 (4)	0.055 (4)	0.004 (3)	0.000 (3)	0.004 (3)
C5	0.043 (3)	0.062 (4)	0.043 (3)	0.002 (3)	0.006 (3)	0.005 (3)
C6	0.063 (4)	0.081 (5)	0.065 (4)	−0.015 (4)	−0.002 (4)	0.014 (4)
C7	0.073 (5)	0.095 (6)	0.094 (6)	−0.016 (4)	0.009 (4)	0.030 (5)
C8	0.090 (6)	0.066 (5)	0.116 (8)	−0.021 (4)	−0.007 (5)	0.000 (5)
C9	0.063 (4)	0.069 (4)	0.074 (4)	−0.002 (3)	0.002 (3)	−0.007 (4)
C10	0.040 (3)	0.086 (5)	0.053 (4)	−0.001 (3)	−0.008 (3)	−0.004 (4)
C11	0.028 (2)	0.063 (4)	0.058 (3)	0.003 (2)	0.000 (3)	0.006 (3)
C12	0.043 (3)	0.065 (4)	0.054 (4)	−0.001 (3)	0.002 (3)	0.006 (3)
C13	0.044 (3)	0.058 (4)	0.063 (4)	0.001 (3)	0.000 (3)	−0.003 (3)
C14	0.038 (3)	0.068 (4)	0.047 (3)	0.004 (3)	−0.001 (3)	0.004 (3)
C15	0.047 (3)	0.068 (4)	0.047 (3)	0.005 (3)	0.002 (3)	0.002 (3)
C16	0.060 (3)	0.058 (4)	0.040 (3)	−0.001 (3)	−0.005 (3)	0.002 (3)
C17	0.062 (4)	0.076 (4)	0.049 (3)	0.011 (3)	−0.003 (3)	−0.004 (3)
C18	0.061 (3)	0.089 (5)	0.048 (4)	−0.006 (3)	−0.002 (3)	−0.003 (4)
C19	0.078 (4)	0.082 (5)	0.051 (4)	−0.011 (4)	−0.010 (3)	0.024 (4)
C20	0.071 (4)	0.063 (4)	0.071 (4)	0.003 (3)	−0.004 (3)	0.013 (4)
C21	0.064 (4)	0.067 (4)	0.052 (3)	0.001 (3)	0.000 (3)	−0.002 (3)
C22	0.097 (6)	0.216 (11)	0.046 (4)	−0.007 (7)	−0.009 (5)	−0.005 (6)

Geometric parameters (Å, º)

O1—C10	1.238 (7)	C9—C13	1.362 (9)
O2—C18	1.363 (8)	C9—H9	0.9300
O2—C22	1.430 (9)	C10—C14	1.447 (9)
C1—C2	1.357 (10)	C10—C13	1.492 (8)
C1—C14	1.389 (8)	C11—C14	1.409 (8)
C1—H1	0.9300	C12—C13	1.412 (9)
C2—C3	1.376 (11)	C15—C16	1.468 (8)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.378 (9)	C16—C17	1.382 (8)
C3—H3	0.9300	C16—C21	1.393 (8)
C4—C11	1.372 (8)	C17—C18	1.387 (9)
C4—H4	0.9300	C17—H17	0.9300
C5—C15	1.354 (8)	C18—C19	1.344 (9)
C5—C12	1.462 (8)	C19—C20	1.375 (10)
C5—C11	1.483 (8)	C19—H19	0.9300
C6—C7	1.371 (11)	C20—C21	1.386 (9)
C6—C12	1.395 (9)	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.385 (11)	C22—H22A	0.9599
C7—H7	0.9300	C22—H22B	0.9599
C8—C9	1.363 (11)	C22—H22C	0.9599
C8—H8	0.9300
C18—O2—C22	117.3 (6)	C6—C12—C5	122.3 (6)
C2—C1—C14	121.5 (7)	C13—C12—C5	120.4 (5)
C2—C1—H1	119.2	C9—C13—C12	121.0 (6)
C14—C1—H1	119.2	C9—C13—C10	120.2 (6)
C1—C2—C3	119.3 (6)	C12—C13—C10	118.7 (5)
C1—C2—H2	120.3	C1—C14—C11	119.6 (6)
C3—C2—H2	120.3	C1—C14—C10	119.5 (6)
C2—C3—C4	119.9 (7)	C11—C14—C10	120.9 (5)
C2—C3—H3	120.1	C5—C15—C16	131.5 (6)
C4—C3—H3	120.1	C5—C15—H15	114.2
C11—C4—C3	122.2 (6)	C16—C15—H15	114.2
C11—C4—H4	118.9	C17—C16—C21	118.1 (5)
C3—C4—H4	118.9	C17—C16—C15	119.9 (5)
C15—C5—C12	124.6 (5)	C21—C16—C15	121.9 (5)
C15—C5—C11	118.3 (5)	C16—C17—C18	121.5 (6)
C12—C5—C11	117.0 (5)	C16—C17—H17	119.2
C7—C6—C12	120.4 (7)	C18—C17—H17	119.2
C7—C6—H6	119.8	C19—C18—O2	125.7 (6)
C12—C6—H6	119.8	C19—C18—C17	119.3 (6)
C6—C7—C8	121.3 (7)	O2—C18—C17	115.0 (6)
C6—C7—H7	119.4	C18—C19—C20	121.3 (6)
C8—C7—H7	119.4	C18—C19—H19	119.4
C9—C8—C7	118.7 (7)	C20—C19—H19	119.4
C9—C8—H8	120.6	C19—C20—C21	119.8 (6)
C7—C8—H8	120.6	C19—C20—H20	120.1
C13—C9—C8	121.2 (7)	C21—C20—H20	120.1
C13—C9—H9	119.4	C20—C21—C16	120.0 (6)
C8—C9—H9	119.4	C20—C21—H21	120.0
O1—C10—C14	122.1 (6)	C16—C21—H21	120.0
O1—C10—C13	119.6 (6)	O2—C22—H22A	109.5
C14—C10—C13	118.3 (5)	O2—C22—H22B	109.5
C4—C11—C14	117.4 (6)	H22A—C22—H22B	109.5
C4—C11—C5	123.7 (6)	O2—C22—H22C	109.5
C14—C11—C5	118.8 (5)	H22A—C22—H22C	109.5
C6—C12—C13	117.1 (6)	H22B—C22—H22C	109.5
C14—C1—C2—C3	−0.1 (10)	C14—C10—C13—C12	−14.8 (8)
C1—C2—C3—C4	1.3 (10)	C2—C1—C14—C11	−1.7 (9)
C2—C3—C4—C11	−0.6 (9)	C2—C1—C14—C10	177.9 (6)
C12—C6—C7—C8	−0.8 (11)	C4—C11—C14—C1	2.3 (8)
C6—C7—C8—C9	−2.1 (13)	C5—C11—C14—C1	−174.8 (5)
C7—C8—C9—C13	1.1 (12)	C4—C11—C14—C10	−177.2 (5)
C3—C4—C11—C14	−1.2 (8)	C5—C11—C14—C10	5.7 (7)
C3—C4—C11—C5	175.7 (5)	O1—C10—C14—C1	10.8 (9)
C15—C5—C11—C4	−25.0 (7)	C13—C10—C14—C1	−165.8 (5)
C12—C5—C11—C4	159.1 (5)	O1—C10—C14—C11	−169.7 (6)
C15—C5—C11—C14	151.9 (5)	C13—C10—C14—C11	13.8 (7)
C12—C5—C11—C14	−24.0 (7)	C12—C5—C15—C16	9.2 (10)
C7—C6—C12—C13	4.4 (9)	C11—C5—C15—C16	−166.3 (5)
C7—C6—C12—C5	179.3 (6)	C5—C15—C16—C17	−145.5 (6)
C15—C5—C12—C6	32.7 (8)	C5—C15—C16—C21	39.7 (9)
C11—C5—C12—C6	−151.7 (5)	C21—C16—C17—C18	0.2 (9)
C15—C5—C12—C13	−152.6 (6)	C15—C16—C17—C18	−174.8 (6)
C11—C5—C12—C13	23.0 (8)	C22—O2—C18—C19	4.8 (11)
C8—C9—C13—C12	2.8 (10)	C22—O2—C18—C17	−176.0 (7)
C8—C9—C13—C10	−173.8 (7)	C16—C17—C18—C19	−0.2 (10)
C6—C12—C13—C9	−5.4 (9)	C16—C17—C18—O2	−179.4 (6)
C5—C12—C13—C9	179.6 (5)	O2—C18—C19—C20	−179.6 (6)
C6—C12—C13—C10	171.2 (5)	C17—C18—C19—C20	1.2 (10)
C5—C12—C13—C10	−3.8 (8)	C18—C19—C20—C21	−2.3 (10)
O1—C10—C13—C9	−14.8 (8)	C19—C20—C21—C16	2.3 (9)
C14—C10—C13—C9	161.8 (5)	C17—C16—C21—C20	−1.3 (9)
O1—C10—C13—C12	168.6 (6)	C15—C16—C21—C20	173.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.93	2.40	3.298 (10)	163
C20—H20···O1^ii	0.93	2.51	3.441 (8)	174

Symmetry codes: (i) −x, −y+1, z+1/2; (ii) −x+1, −y+1, z+1/2.