12-(4-Chloro-phen-yl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one.

The title compound, C(25)H(21)ClO(2), was synthesized via the three-component coupling of 4-chloro-benzaldehyde, 2-naphthol and 5,5-dimethyl-cyclo-hexane-1,3-dione. The pyran ring adopts a boat conformation, while the cyclo-hexenone ring is in an envelope conformation. The 4-chloro-phenyl ring is almost perpendicular to the pyran ring [dihedral angle = 87.39 (1)°]. In the crystal, mol-ecules are connected by inter-molecular 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 = 388.87

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.136

S = 0.91

4667 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.50 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H21ClO2	F(000) = 816
Mr = 388.87	Dx = 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

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

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(Fo2) + (0.0704P)2] where P = (Fo2 + 2Fc2)/3
4667 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.50 e Å−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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .