12-(4-Chloro­phen­yl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one

Li, D.-L.; Wang, L.-H.

doi:10.1107/S1600536810004125

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o547

doi:10.1107/S1600536810004125

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12-(4-Chlorophenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one

De-Ling Li ^a ^* and Li-Hong Wang ^a

^aDepartment of Chemistry, Tangshan Normal College, Tangshan 063000, People's Republic of China
^*Correspondence e-mail: deling1@126.com

(Received 3 November 2009; accepted 2 February 2010; online 6 February 2010)

The title compound, C₂₅H₂₁ClO₂, was synthesized via the three-component coupling of 4-chlorobenzaldehyde, 2-naphthol and 5,5-dimethylcyclohexane-1,3-dione. The pyran ring adopts a boat conformation, while the cyclohexenone ring is in an envelope conformation. The 4-chlorophenyl ring is almost perpendicular to the pyran ring [dihedral angle = 87.39 (1)°]. In the crystal, molecules are connected by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of xanthenes and benzoxanthenes, see: Poupelin et al. (1978 ); Lambert et al. (1997 ) and for their applications see: Ion et al. (1998 ); Saint-Ruf et al. (1975 ).

Experimental

Crystal data

C₂₅H₂₁ClO₂
M_r = 388.87
Monoclinic, P 2₁ /n
a = 10.293 (2) Å
b = 11.621 (2) Å
c = 16.447 (3) Å
β = 90.04 (3)°
V = 1967.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 113 K
0.16 × 0.14 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.967, T_max = 0.983
15871 measured reflections
4667 independent reflections
2863 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.136
S = 0.91
4667 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯O2ⁱ	0.95	2.56	3.376 (2)	144
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004125/bv2134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004125/bv2134Isup2.hkl

checkCIF report

Comment top

Xanthenes and benzoxanthenes are important biologically active heterocycles. They possess anti-inflammatory (Poupelin et al., 1978) and antiviral (Lambert et al., 1997) activities. These compounds are utilized as antagonists for paralyzing action of zoxazolamine (Saint-Ruf et al.,1975) and in photodynamic therapy (Ion et al.,1998). We report herein the crystal structure of the title compound.

The pyran ring of the title molecule (Fig.1) adopts a boat conformation. The cyclohexenone ring is in an envelope conformation with atom C15 at the flap. The 4-chloropheny ring and the planar part of the pyran ring (C1/C10/C12/C17) are nearly perpendicular to each other, with a dihedral angle of 87.39 (1)°. In the crystal, the molecules are connected by C—H···O hydrogen bonds.

Related literature top

For the biological activity of xanthenes and benzoxanthenes, see: Poupelin et al. (1978); Lambert et al. (1997) and for their applications see: Ion et al. (1998); Saint-Ruf et al. (1975).

Experimental top

To a mixture of 2-naphthol (1.0 mmol), 4-chlorobenzaldehyde (1.0 mmol), and 5,5-dimethylcyclohexane-1,3-dione (1.1 mmol) was added strontium trifluoromethanesulfonate (0.1 mmol) in 1,2-dichloroethane (2 ml). The mixture was stirred at 80 °C for 5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, water was added and the product was extracted with ethyl acetate (3 x 10 ml). The organic layer was dried (MgSO₄)and evaporated, and the crude product was purified by flash chromatography on silica gel. Pure product crystallized slowly at room temperature in ethanol. A single-crystal was obtained by slow evaporation of a solution in ethanol.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I), showing the atom-numbering scheme. Dispacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The packing, showing hydrogen-bond interactions as dashed lines, H atoms are shown as small spheres of arbitary radii.

12-(4-Chlorophenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen- 11(12H)-one top

Crystal data top

C₂₅H₂₁ClO₂	F(000) = 816
M_r = 388.87	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.293 (2) Å	Cell parameters from 5755 reflections
b = 11.621 (2) Å	θ = 2.2–27.8°
c = 16.447 (3) Å	µ = 0.21 mm⁻¹
β = 90.04 (3)°	T = 113 K
V = 1967.3 (7) Å³	Prism, colourless
Z = 4	0.16 × 0.14 × 0.08 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4667 independent reflections
Radiation source: rotating anode	2863 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.079
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ω and ϕ scans	h = −12→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
T_min = 0.967, T_max = 0.983	l = −16→21
15871 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0704P)²] where P = (F_o² + 2F_c²)/3
4667 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₂₅H₂₁ClO₂	V = 1967.3 (7) Å³
M_r = 388.87	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.293 (2) Å	µ = 0.21 mm⁻¹
b = 11.621 (2) Å	T = 113 K
c = 16.447 (3) Å	0.16 × 0.14 × 0.08 mm
β = 90.04 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4667 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2863 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.983	R_int = 0.079
15871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 0.91	Δρ_max = 0.43 e Å⁻³
4667 reflections	Δρ_min = −0.50 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.73445 (5)	0.84810 (5)	1.12407 (3)	0.03409 (17)
O1	0.32484 (13)	0.87906 (11)	0.73299 (7)	0.0238 (3)
O2	0.25555 (13)	0.57878 (11)	0.92168 (7)	0.0263 (3)
C1	0.44337 (19)	0.83375 (16)	0.70869 (10)	0.0209 (4)
C2	0.4964 (2)	0.88806 (17)	0.63881 (10)	0.0245 (4)
H2	0.4497	0.9473	0.6117	0.029*
C3	0.6149 (2)	0.85411 (17)	0.61122 (11)	0.0257 (5)
H3	0.6517	0.8917	0.5654	0.031*
C4	0.68478 (19)	0.76365 (17)	0.64948 (10)	0.0241 (4)
C5	0.8075 (2)	0.72738 (18)	0.62115 (11)	0.0290 (5)
H5	0.8463	0.7659	0.5764	0.035*
C6	0.8714 (2)	0.63750 (19)	0.65724 (11)	0.0302 (5)
H6	0.9544	0.6146	0.6378	0.036*
C7	0.8141 (2)	0.57895 (18)	0.72317 (11)	0.0287 (5)
H7	0.8577	0.5153	0.7471	0.034*
C8	0.6959 (2)	0.61332 (17)	0.75303 (11)	0.0244 (4)
H8	0.6596	0.5739	0.7982	0.029*
C9	0.62679 (18)	0.70654 (16)	0.71777 (10)	0.0215 (4)
C10	0.50399 (18)	0.74502 (16)	0.74811 (10)	0.0199 (4)
C11	0.44318 (18)	0.69161 (16)	0.82395 (10)	0.0202 (4)
H11	0.4478	0.6059	0.8194	0.024*
C12	0.30257 (18)	0.72721 (16)	0.82882 (10)	0.0202 (4)
C13	0.21423 (19)	0.66017 (16)	0.88135 (10)	0.0211 (4)
C14	0.07188 (19)	0.69208 (17)	0.88032 (11)	0.0261 (4)
H14A	0.0309	0.6643	0.9311	0.031*
H14B	0.0292	0.6524	0.8342	0.031*
C15	0.0482 (2)	0.82193 (17)	0.87251 (11)	0.0260 (5)
C16	0.11871 (19)	0.86281 (17)	0.79483 (11)	0.0248 (4)
H16A	0.0684	0.8377	0.7467	0.030*
H16B	0.1215	0.9480	0.7945	0.030*
C17	0.25322 (19)	0.81783 (16)	0.78815 (10)	0.0216 (4)
C18	−0.0967 (2)	0.8461 (2)	0.86518 (14)	0.0378 (6)
H18A	−0.1110	0.9294	0.8622	0.057*
H18B	−0.1418	0.8149	0.9128	0.057*
H18C	−0.1305	0.8095	0.8158	0.057*
C19	0.1024 (2)	0.88391 (19)	0.94769 (12)	0.0323 (5)
H19A	0.0891	0.9670	0.9419	0.048*
H19B	0.1955	0.8677	0.9528	0.048*
H19C	0.0571	0.8565	0.9964	0.048*
C20	0.51814 (18)	0.72951 (16)	0.90026 (10)	0.0196 (4)
C21	0.53737 (19)	0.84537 (16)	0.91539 (10)	0.0217 (4)
H21	0.5033	0.9007	0.8785	0.026*
C22	0.60548 (19)	0.88237 (17)	0.98344 (10)	0.0227 (4)
H22	0.6193	0.9620	0.9930	0.027*
C23	0.65267 (18)	0.80068 (18)	1.03694 (10)	0.0235 (4)
C24	0.63531 (19)	0.68441 (18)	1.02455 (11)	0.0261 (4)
H24	0.6684	0.6298	1.0622	0.031*
C25	0.5679 (2)	0.64900 (17)	0.95526 (11)	0.0245 (4)
H25	0.5556	0.5692	0.9454	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0361 (4)	0.0441 (4)	0.0221 (3)	−0.0042 (2)	−0.0111 (2)	0.0026 (2)
O1	0.0252 (8)	0.0268 (8)	0.0194 (7)	0.0030 (6)	0.0051 (5)	0.0050 (5)
O2	0.0293 (9)	0.0257 (8)	0.0239 (7)	0.0018 (6)	0.0032 (6)	0.0039 (5)
C1	0.0202 (11)	0.0275 (11)	0.0148 (9)	−0.0006 (8)	0.0025 (7)	−0.0025 (7)
C2	0.0312 (12)	0.0260 (11)	0.0163 (9)	−0.0007 (9)	0.0001 (8)	0.0023 (7)
C3	0.0294 (12)	0.0331 (12)	0.0146 (9)	−0.0039 (9)	0.0043 (8)	0.0002 (7)
C4	0.0267 (11)	0.0302 (11)	0.0154 (9)	−0.0041 (9)	0.0030 (7)	−0.0036 (7)
C5	0.0263 (12)	0.0398 (13)	0.0208 (10)	−0.0025 (9)	0.0071 (8)	−0.0026 (8)
C6	0.0235 (12)	0.0424 (13)	0.0248 (10)	0.0021 (9)	0.0051 (8)	−0.0052 (9)
C7	0.0280 (12)	0.0350 (13)	0.0231 (10)	0.0047 (9)	0.0001 (8)	−0.0011 (8)
C8	0.0241 (11)	0.0320 (12)	0.0172 (9)	0.0012 (9)	0.0014 (7)	−0.0014 (7)
C9	0.0219 (11)	0.0279 (11)	0.0147 (8)	−0.0027 (8)	0.0008 (7)	−0.0039 (7)
C10	0.0224 (11)	0.0234 (11)	0.0138 (8)	−0.0028 (8)	0.0002 (7)	−0.0025 (7)
C11	0.0228 (11)	0.0225 (10)	0.0152 (8)	0.0026 (8)	0.0002 (7)	−0.0007 (7)
C12	0.0222 (11)	0.0242 (10)	0.0143 (8)	−0.0007 (8)	0.0002 (7)	−0.0023 (7)
C13	0.0231 (11)	0.0204 (10)	0.0197 (9)	−0.0007 (8)	−0.0002 (7)	−0.0035 (7)
C14	0.0231 (12)	0.0303 (12)	0.0250 (10)	−0.0031 (9)	0.0033 (8)	0.0015 (8)
C15	0.0243 (12)	0.0297 (12)	0.0240 (10)	0.0035 (9)	0.0039 (8)	0.0020 (8)
C16	0.0235 (12)	0.0300 (11)	0.0210 (9)	0.0035 (9)	−0.0007 (7)	0.0009 (8)
C17	0.0242 (11)	0.0265 (11)	0.0140 (8)	−0.0012 (8)	0.0026 (7)	−0.0023 (7)
C18	0.0275 (13)	0.0428 (15)	0.0432 (13)	0.0074 (10)	0.0068 (10)	0.0099 (10)
C19	0.0425 (15)	0.0304 (12)	0.0240 (10)	0.0051 (10)	0.0072 (9)	−0.0021 (8)
C20	0.0183 (10)	0.0262 (11)	0.0143 (8)	0.0020 (8)	0.0034 (7)	0.0016 (7)
C21	0.0238 (11)	0.0254 (11)	0.0158 (9)	0.0030 (8)	0.0000 (7)	0.0029 (7)
C22	0.0240 (11)	0.0250 (11)	0.0192 (9)	0.0012 (8)	−0.0002 (7)	0.0002 (7)
C23	0.0206 (11)	0.0347 (12)	0.0152 (9)	0.0015 (9)	0.0008 (7)	0.0003 (8)
C24	0.0261 (12)	0.0335 (12)	0.0188 (9)	0.0023 (9)	−0.0012 (8)	0.0070 (8)
C25	0.0293 (12)	0.0242 (11)	0.0199 (9)	0.0015 (9)	0.0019 (8)	0.0026 (7)

Geometric parameters (Å, º) top

Cl1—C23	1.7504 (19)	C13—C14	1.511 (3)
O1—C17	1.369 (2)	C14—C15	1.534 (3)
O1—C1	1.388 (2)	C14—H14A	0.9900
O2—C13	1.231 (2)	C14—H14B	0.9900
C1—C10	1.368 (3)	C15—C18	1.523 (3)
C1—C2	1.420 (3)	C15—C19	1.536 (3)
C2—C3	1.361 (3)	C15—C16	1.545 (3)
C2—H2	0.9500	C16—C17	1.484 (3)
C3—C4	1.420 (3)	C16—H16A	0.9900
C3—H3	0.9500	C16—H16B	0.9900
C4—C5	1.411 (3)	C18—H18A	0.9800
C4—C9	1.435 (2)	C18—H18B	0.9800
C5—C6	1.370 (3)	C18—H18C	0.9800
C5—H5	0.9500	C19—H19A	0.9800
C6—C7	1.410 (3)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800
C7—C8	1.372 (3)	C20—C21	1.383 (3)
C7—H7	0.9500	C20—C25	1.398 (2)
C8—C9	1.420 (3)	C21—C22	1.389 (3)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.431 (3)	C22—C23	1.382 (3)
C10—C11	1.528 (2)	C22—H22	0.9500
C11—C12	1.507 (3)	C23—C24	1.378 (3)
C11—C20	1.537 (2)	C24—C25	1.396 (3)
C11—H11	1.0000	C24—H24	0.9500
C12—C17	1.347 (3)	C25—H25	0.9500
C12—C13	1.477 (3)

C17—O1—C1	117.88 (15)	C15—C14—H14B	108.9
C10—C1—O1	123.37 (16)	H14A—C14—H14B	107.7
C10—C1—C2	122.89 (18)	C18—C15—C14	110.08 (17)
O1—C1—C2	113.74 (17)	C18—C15—C19	109.41 (17)
C3—C2—C1	119.07 (18)	C14—C15—C19	109.66 (16)
C3—C2—H2	120.5	C18—C15—C16	109.79 (17)
C1—C2—H2	120.5	C14—C15—C16	107.30 (16)
C2—C3—C4	121.38 (17)	C19—C15—C16	110.58 (17)
C2—C3—H3	119.3	C17—C16—C15	113.05 (16)
C4—C3—H3	119.3	C17—C16—H16A	109.0
C5—C4—C3	121.86 (17)	C15—C16—H16A	109.0
C5—C4—C9	119.55 (19)	C17—C16—H16B	109.0
C3—C4—C9	118.58 (18)	C15—C16—H16B	109.0
C6—C5—C4	120.98 (18)	H16A—C16—H16B	107.8
C6—C5—H5	119.5	C12—C17—O1	122.17 (17)
C4—C5—H5	119.5	C12—C17—C16	126.17 (17)
C5—C6—C7	120.03 (19)	O1—C17—C16	111.65 (16)
C5—C6—H6	120.0	C15—C18—H18A	109.5
C7—C6—H6	120.0	C15—C18—H18B	109.5
C8—C7—C6	120.4 (2)	H18A—C18—H18B	109.5
C8—C7—H7	119.8	C15—C18—H18C	109.5
C6—C7—H7	119.8	H18A—C18—H18C	109.5
C7—C8—C9	121.35 (18)	H18B—C18—H18C	109.5
C7—C8—H8	119.3	C15—C19—H19A	109.5
C9—C8—H8	119.3	C15—C19—H19B	109.5
C8—C9—C10	122.59 (16)	H19A—C19—H19B	109.5
C8—C9—C4	117.64 (17)	C15—C19—H19C	109.5
C10—C9—C4	119.76 (18)	H19A—C19—H19C	109.5
C1—C10—C9	118.22 (16)	H19B—C19—H19C	109.5
C1—C10—C11	120.41 (16)	C21—C20—C25	118.86 (17)
C9—C10—C11	121.34 (16)	C21—C20—C11	119.82 (16)
C12—C11—C10	109.01 (15)	C25—C20—C11	121.32 (17)
C12—C11—C20	111.06 (14)	C20—C21—C22	121.22 (17)
C10—C11—C20	110.16 (15)	C20—C21—H21	119.4
C12—C11—H11	108.9	C22—C21—H21	119.4
C10—C11—H11	108.9	C23—C22—C21	118.53 (18)
C20—C11—H11	108.9	C23—C22—H22	120.7
C17—C12—C13	118.09 (17)	C21—C22—H22	120.7
C17—C12—C11	123.37 (17)	C24—C23—C22	122.26 (18)
C13—C12—C11	118.54 (16)	C24—C23—Cl1	119.47 (14)
O2—C13—C12	120.53 (18)	C22—C23—Cl1	118.26 (16)
O2—C13—C14	121.94 (17)	C23—C24—C25	118.30 (17)
C12—C13—C14	117.47 (16)	C23—C24—H24	120.8
C13—C14—C15	113.33 (16)	C25—C24—H24	120.8
C13—C14—H14A	108.9	C24—C25—C20	120.83 (19)
C15—C14—H14A	108.9	C24—C25—H25	119.6
C13—C14—H14B	108.9	C20—C25—H25	119.6

C17—O1—C1—C10	−13.7 (3)	C17—C12—C13—O2	−177.76 (17)
C17—O1—C1—C2	166.34 (15)	C11—C12—C13—O2	1.7 (2)
C10—C1—C2—C3	−2.7 (3)	C17—C12—C13—C14	5.0 (2)
O1—C1—C2—C3	177.34 (17)	C11—C12—C13—C14	−175.55 (15)
C1—C2—C3—C4	1.7 (3)	O2—C13—C14—C15	146.05 (17)
C2—C3—C4—C5	179.68 (18)	C12—C13—C14—C15	−36.7 (2)
C2—C3—C4—C9	1.0 (3)	C13—C14—C15—C18	175.54 (16)
C3—C4—C5—C6	−177.85 (18)	C13—C14—C15—C19	−64.0 (2)
C9—C4—C5—C6	0.8 (3)	C13—C14—C15—C16	56.1 (2)
C4—C5—C6—C7	0.7 (3)	C18—C15—C16—C17	−166.12 (17)
C5—C6—C7—C8	−1.7 (3)	C14—C15—C16—C17	−46.5 (2)
C6—C7—C8—C9	1.3 (3)	C19—C15—C16—C17	73.1 (2)
C7—C8—C9—C10	−179.36 (18)	C13—C12—C17—O1	−174.47 (15)
C7—C8—C9—C4	0.1 (3)	C11—C12—C17—O1	6.1 (3)
C5—C4—C9—C8	−1.2 (3)	C13—C12—C17—C16	4.3 (3)
C3—C4—C9—C8	177.50 (17)	C11—C12—C17—C16	−175.15 (16)
C5—C4—C9—C10	178.32 (17)	C1—O1—C17—C12	11.2 (3)
C3—C4—C9—C10	−3.0 (3)	C1—O1—C17—C16	−167.72 (15)
O1—C1—C10—C9	−179.32 (16)	C15—C16—C17—C12	18.3 (3)
C2—C1—C10—C9	0.7 (3)	C15—C16—C17—O1	−162.83 (15)
O1—C1—C10—C11	−1.1 (3)	C12—C11—C20—C21	−66.9 (2)
C2—C1—C10—C11	178.86 (17)	C10—C11—C20—C21	54.0 (2)
C8—C9—C10—C1	−178.37 (17)	C12—C11—C20—C25	113.16 (19)
C4—C9—C10—C1	2.1 (3)	C10—C11—C20—C25	−125.96 (18)
C8—C9—C10—C11	3.5 (3)	C25—C20—C21—C22	0.5 (3)
C4—C9—C10—C11	−176.02 (16)	C11—C20—C21—C22	−179.52 (16)
C1—C10—C11—C12	16.0 (2)	C20—C21—C22—C23	−0.9 (3)
C9—C10—C11—C12	−165.92 (16)	C21—C22—C23—C24	0.6 (3)
C1—C10—C11—C20	−106.13 (19)	C21—C22—C23—Cl1	−178.22 (14)
C9—C10—C11—C20	72.0 (2)	C22—C23—C24—C25	0.2 (3)
C10—C11—C12—C17	−18.8 (2)	Cl1—C23—C24—C25	178.95 (15)
C20—C11—C12—C17	102.80 (19)	C23—C24—C25—C20	−0.6 (3)
C10—C11—C12—C13	161.81 (15)	C21—C20—C25—C24	0.3 (3)
C20—C11—C12—C13	−76.6 (2)	C11—C20—C25—C24	−179.72 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O2ⁱ	0.95	2.56	3.376 (2)	144

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁ClO₂
M_r	388.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	10.293 (2), 11.621 (2), 16.447 (3)
β (°)	90.04 (3)
V (Å³)	1967.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.16 × 0.14 × 0.08

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.967, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15871, 4667, 2863
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.136, 0.91
No. of reflections	4667
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.50

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O2ⁱ	0.95	2.56	3.376 (2)	144.1

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

The authors thank the Tangshan Municipal Science and Technology Commission (No. 07160213B) and Tangshan Normal College (No. 07 A02) for financial support.

References

Ion, R. M., Planner, A., Wiktorowicz, K. & Frackowiak, D. (1998). Acta Biochim. Pol. 45, 833–845. Web of Science CAS PubMed Google Scholar
Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178, 1–80. Google Scholar
Poupelin, J. P., Saint-Ruf, G. Foussard-Blanpin, G. O., Narcisse, G., Uchida-Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67–71. CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Saint-Ruf, G., Hieu, H. T. & Poupelin, J. P. (1975). Naturwissenschaften, 62, 584–585. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 3| March 2010| Page o547

doi:10.1107/S1600536810004125

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

12-(4-Chloro­phen­yl)-9,9-di­methyl-9,10-di­hydro-8H-benzo[a]xanthen-11(12H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

12-(4-Chlorophenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one