Methyl 7-meth-oxy-9-oxo-9H-xanthene-2-carboxyl-ate.

The crystal structure of the title compound, C(16)H(12)O(5), is stabilized by C-H⋯O hydrogen bonds and C=O⋯π inter-actions; π-π inter-actions are also present. With respective average deviations from planarity of 0.003 (2) and 0.002 (1) Å, the xanthone and ester fragments are oriented at an angle of 2.8 (2)° with respect to each other. The mean planes of the xanthone skeleton lie either parallel to each other or are inclined at an angle of 85.5 (2)° in the crystal structure.

Related literature

For general background and uses of xanthones, see: Chen et al. (1993 ▶); Denisova-Dyatlova & Glyzin (1982 ▶); Fukai et al. (2005 ▶); Gopalakrishnan et al. (1997 ▶); Ignatushchenko et al. (2000 ▶); Ito et al. (2003 ▶); Librowski et al. (2005 ▶); Pfister et al. (1972 ▶, 1980 ▶). For related structures, see: Evans et al. (2004 ▶); Shi et al. (2004 ▶); Macias et al. (2001 ▶). For synthesis, see: Geertsema et al. (2006 ▶). For background to the various types of inter­molecular inter­actions, see: Bianchi et al. (2004 ▶); Steiner (1999 ▶) Santos-Contreras et al. (2007 ▶); Hunter & Sanders (1990 ▶). For analysis of inter­molecular inter­actions, see: Spek (2003 ▶).

Experimental

Crystal data

C16H12O5

M = 284.26

Monoclinic,

a = 4.7709 (4) Å

b = 10.5375 (8) Å

c = 26.7854 (19) Å

β = 93.266 (7)°

V = 1344.40 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 (2) K

0.20 × 0.04 × 0.04 mm

Data collection

Oxford Diffraction Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.994, T max = 0.997

23842 measured reflections

2366 independent reflections

1051 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 0.81

2366 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003602/xu2476sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003602/xu2476Isup2.hkl

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

C16H12O5	F(000) = 592.0
Mr = 284.26	Dx = 1.404 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2126 reflections
a = 4.7709 (4) Å	θ = 3.0–25.0°
b = 10.5375 (8) Å	µ = 0.11 mm−1
c = 26.7854 (19) Å	T = 295 K
β = 93.266 (7)°	Needle, white
V = 1344.40 (18) Å3	0.2 × 0.04 × 0.04 mm
Z = 4

Oxford Diffraction Ruby CCD diffractometer	2366 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1051 reflections with I > 2σ(I)
graphite	Rint = 0.086
Detector resolution: 10.4002 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −12→12
Tmin = 0.994, Tmax = 0.997	l = −31→31
23842 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 0.81	w = 1/[σ2(Fo2) + (0.0471P)2] where P = (Fo2 + 2Fc2)/3
2366 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Experimental. CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.4869 (4)	0.3741 (2)	0.37390 (8)	0.0507 (6)
H1	0.4950	0.4005	0.3409	0.061*
C2	0.6568 (4)	0.4321 (2)	0.41017 (8)	0.0531 (6)
C3	0.6434 (5)	0.3912 (2)	0.45962 (9)	0.0678 (7)
H3	0.7584	0.4289	0.4846	0.081*
C4	0.4634 (5)	0.2964 (3)	0.47187 (9)	0.0735 (7)
H4	0.4548	0.2703	0.5049	0.088*
C5	−0.2272 (5)	−0.0083 (2)	0.43087 (9)	0.0742 (7)
H5	−0.2221	−0.0287	0.4647	0.089*
C6	−0.4064 (5)	−0.0705 (2)	0.39752 (9)	0.0723 (7)
H6	−0.5229	−0.1337	0.4089	0.087*
C7	−0.4169 (4)	−0.0408 (2)	0.34712 (9)	0.0570 (6)
C8	−0.2448 (4)	0.0520 (2)	0.33022 (8)	0.0506 (6)
H8	−0.2514	0.0723	0.2964	0.061*
C9	0.1240 (4)	0.2157 (2)	0.34601 (8)	0.0485 (5)
O10	0.1221 (3)	0.14529 (15)	0.44927 (5)	0.0685 (5)
C11	0.3026 (4)	0.2770 (2)	0.38514 (7)	0.0469 (5)
C12	0.2945 (4)	0.2399 (2)	0.43445 (8)	0.0567 (6)
C13	−0.0592 (4)	0.1163 (2)	0.36375 (7)	0.0459 (5)
C14	−0.0538 (4)	0.0853 (2)	0.41369 (8)	0.0567 (6)
C15	0.8493 (5)	0.5368 (2)	0.39863 (10)	0.0616 (6)
O16	0.9949 (4)	0.59309 (17)	0.42912 (7)	0.0897 (6)
O17	0.8478 (3)	0.56064 (15)	0.34987 (6)	0.0748 (5)
C18	1.0307 (5)	0.6610 (2)	0.33454 (10)	0.0877 (8)
H18A	0.9931	0.6783	0.2996	0.132*
H18B	1.2228	0.6352	0.3403	0.132*
H18C	0.9978	0.7362	0.3536	0.132*
O19	−0.6050 (3)	−0.10926 (15)	0.31785 (6)	0.0734 (5)
C20	−0.6235 (5)	−0.0814 (3)	0.26581 (9)	0.0837 (8)
H20A	−0.7623	−0.1351	0.2493	0.126*
H20B	−0.4446	−0.0962	0.2522	0.126*
H20C	−0.6760	0.0058	0.2609	0.126*
O21	0.1291 (3)	0.24526 (14)	0.30176 (5)	0.0657 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0541 (13)	0.0547 (16)	0.0427 (13)	0.0009 (12)	−0.0024 (11)	−0.0013 (11)
C2	0.0517 (13)	0.0553 (16)	0.0518 (15)	−0.0049 (11)	−0.0025 (11)	−0.0058 (12)
C3	0.0741 (15)	0.0794 (19)	0.0481 (16)	−0.0117 (14)	−0.0139 (11)	−0.0116 (14)
C4	0.0851 (17)	0.087 (2)	0.0471 (14)	−0.0246 (16)	−0.0071 (13)	0.0017 (14)
C5	0.0855 (16)	0.084 (2)	0.0519 (15)	−0.0292 (15)	−0.0047 (13)	0.0166 (14)
C6	0.0777 (16)	0.0703 (19)	0.0681 (19)	−0.0229 (14)	−0.0016 (14)	0.0133 (15)
C7	0.0565 (13)	0.0599 (16)	0.0535 (15)	−0.0049 (13)	−0.0053 (11)	0.0004 (13)
C8	0.0532 (12)	0.0517 (15)	0.0464 (13)	−0.0031 (11)	−0.0022 (11)	−0.0001 (11)
C9	0.0491 (13)	0.0508 (15)	0.0449 (14)	0.0006 (11)	−0.0036 (11)	0.0031 (12)
O10	0.0800 (10)	0.0808 (13)	0.0429 (9)	−0.0254 (9)	−0.0104 (8)	0.0102 (8)
C11	0.0475 (12)	0.0498 (15)	0.0427 (13)	−0.0023 (11)	−0.0027 (10)	0.0012 (11)
C12	0.0584 (13)	0.0629 (17)	0.0476 (14)	−0.0139 (13)	−0.0063 (11)	0.0007 (12)
C13	0.0470 (12)	0.0466 (14)	0.0436 (14)	0.0005 (11)	−0.0022 (10)	0.0020 (11)
C14	0.0617 (14)	0.0596 (17)	0.0473 (15)	−0.0124 (12)	−0.0087 (11)	0.0037 (12)
C15	0.0620 (15)	0.0620 (18)	0.0598 (17)	−0.0037 (13)	−0.0044 (12)	−0.0063 (15)
O16	0.1020 (13)	0.0906 (14)	0.0742 (12)	−0.0367 (11)	−0.0143 (10)	−0.0106 (11)
O17	0.0865 (11)	0.0729 (13)	0.0641 (12)	−0.0294 (10)	−0.0039 (9)	0.0052 (9)
C18	0.0935 (18)	0.078 (2)	0.092 (2)	−0.0274 (16)	0.0074 (15)	0.0129 (16)
O19	0.0772 (10)	0.0744 (12)	0.0671 (12)	−0.0265 (9)	−0.0081 (8)	−0.0049 (9)
C20	0.0931 (18)	0.102 (2)	0.0549 (17)	−0.0282 (16)	−0.0058 (13)	−0.0135 (15)
O21	0.0744 (10)	0.0781 (12)	0.0432 (9)	−0.0200 (8)	−0.0084 (7)	0.0105 (8)

C1—C2	1.373 (3)	C9—O21	1.227 (2)
C1—C11	1.394 (3)	C9—C13	1.461 (3)
C1—H1	0.9300	C9—C11	1.462 (3)
C2—C3	1.398 (3)	O10—C12	1.366 (2)
C2—C15	1.480 (3)	O10—C14	1.386 (2)
C3—C4	1.369 (3)	C11—C12	1.380 (3)
C3—H3	0.9300	C13—C14	1.376 (3)
C4—C12	1.384 (3)	C15—O16	1.199 (2)
C4—H4	0.9300	C15—O17	1.330 (3)
C5—C6	1.368 (3)	O17—C18	1.446 (3)
C5—C14	1.383 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.384 (3)	C18—H18C	0.9600
C6—H6	0.9300	O19—C20	1.422 (3)
C7—O19	1.364 (2)	C20—H20A	0.9600
C7—C8	1.370 (3)	C20—H20B	0.9600
C8—C13	1.400 (3)	C20—H20C	0.9600
C8—H8	0.9300
C2—C1—C11	121.9 (2)	C12—C11—C9	120.9 (2)
C2—C1—H1	119.1	C1—C11—C9	121.22 (19)
C11—C1—H1	119.1	O10—C12—C11	122.33 (19)
C1—C2—C3	118.4 (2)	O10—C12—C4	116.0 (2)
C1—C2—C15	122.2 (2)	C11—C12—C4	121.6 (2)
C3—C2—C15	119.4 (2)	C14—C13—C8	119.0 (2)
C4—C3—C2	121.0 (2)	C14—C13—C9	120.5 (2)
C4—C3—H3	119.5	C8—C13—C9	120.44 (19)
C2—C3—H3	119.5	C13—C14—C5	121.0 (2)
C3—C4—C12	119.2 (2)	C13—C14—O10	122.5 (2)
C3—C4—H4	120.4	C5—C14—O10	116.5 (2)
C12—C4—H4	120.4	O16—C15—O17	123.1 (2)
C6—C5—C14	119.2 (2)	O16—C15—C2	124.7 (2)
C6—C5—H5	120.4	O17—C15—C2	112.2 (2)
C14—C5—H5	120.4	C15—O17—C18	116.59 (19)
C5—C6—C7	121.0 (2)	O17—C18—H18A	109.5
C5—C6—H6	119.5	O17—C18—H18B	109.5
C7—C6—H6	119.5	H18A—C18—H18B	109.5
O19—C7—C8	125.1 (2)	O17—C18—H18C	109.5
O19—C7—C6	115.3 (2)	H18A—C18—H18C	109.5
C8—C7—C6	119.6 (2)	H18B—C18—H18C	109.5
C7—C8—C13	120.2 (2)	C7—O19—C20	117.16 (17)
C7—C8—H8	119.9	O19—C20—H20A	109.5
C13—C8—H8	119.9	O19—C20—H20B	109.5
O21—C9—C13	122.78 (19)	H20A—C20—H20B	109.5
O21—C9—C11	122.5 (2)	O19—C20—H20C	109.5
C13—C9—C11	114.73 (19)	H20A—C20—H20C	109.5
C12—O10—C14	118.97 (16)	H20B—C20—H20C	109.5
C12—C11—C1	117.8 (2)
C11—C1—C2—C3	0.3 (3)	C3—C4—C12—C11	−0.1 (4)
C11—C1—C2—C15	−178.91 (19)	C7—C8—C13—C14	−0.3 (3)
C1—C2—C3—C4	−0.6 (3)	C7—C8—C13—C9	−179.76 (19)
C15—C2—C3—C4	178.6 (2)	O21—C9—C13—C14	178.94 (19)
C2—C3—C4—C12	0.6 (4)	C11—C9—C13—C14	−0.7 (3)
C14—C5—C6—C7	−0.2 (4)	O21—C9—C13—C8	−1.6 (3)
C5—C6—C7—O19	−179.7 (2)	C11—C9—C13—C8	178.67 (18)
C5—C6—C7—C8	0.2 (4)	C8—C13—C14—C5	0.3 (3)
O19—C7—C8—C13	−179.99 (19)	C9—C13—C14—C5	179.7 (2)
C6—C7—C8—C13	0.1 (3)	C8—C13—C14—O10	−179.42 (18)
C2—C1—C11—C12	0.1 (3)	C9—C13—C14—O10	0.0 (3)
C2—C1—C11—C9	−179.66 (19)	C6—C5—C14—C13	−0.1 (4)
O21—C9—C11—C12	−179.0 (2)	C6—C5—C14—O10	179.7 (2)
C13—C9—C11—C12	0.7 (3)	C12—O10—C14—C13	0.8 (3)
O21—C9—C11—C1	0.8 (3)	C12—O10—C14—C5	−178.9 (2)
C13—C9—C11—C1	−179.53 (17)	C1—C2—C15—O16	177.5 (2)
C14—O10—C12—C11	−0.8 (3)	C3—C2—C15—O16	−1.7 (4)
C14—O10—C12—C4	179.6 (2)	C1—C2—C15—O17	−3.8 (3)
C1—C11—C12—O10	−179.70 (17)	C3—C2—C15—O17	177.05 (19)
C9—C11—C12—O10	0.1 (3)	O16—C15—O17—C18	−0.8 (3)
C1—C11—C12—C4	−0.2 (3)	C2—C15—O17—C18	−179.59 (18)
C9—C11—C12—C4	179.6 (2)	C8—C7—O19—C20	−0.2 (3)
C3—C4—C12—O10	179.4 (2)	C6—C7—O19—C20	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O16i	0.93	2.54	3.362 (3)	147
C20—H20A···O21ii	0.96	2.50	3.454 (3)	173

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
A	Ciii	3.549 (1)	0.8	3.420 (1)	1.068 (1)
B	Aiii	3.583 (1)	0.1	3.454 (1)	0.953 (1)
B	Ciii	3.772 (1)	0.8	3.455 (1)	1.525 (1)

X	I	J	I···J	X···J	X-I···J
C15	O16	CgBiii	3.564 (2)	3.689 (2)	86.4 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O16i	0.93	2.54	3.362 (3)	147
C20—H20A⋯O21ii	0.96	2.50	3.454 (3)	173

Symmetry codes: (i) ; (ii) .

Table 2

π–π interactions (Å,°)

CgI	CgJ	Cg⋯Cg	Dihedral angle	Interplanar distance	Offset
A	Ciii	3.549 (1)	0.8	3.420 (1)	1.068 (1)
B	Aiii	3.583 (1)	0.1	3.454 (1)	0.953 (1)
B	Ciii	3.772 (1)	0.8	3.455 (1)	1.525 (1)

Symmetry code: (iii) . CgA, CgB and CgC are the centroids of the C9/O10/C11–C14, C1–C4/C12/C11 and C5–C8/C13/C14 rings, respectively. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J.

Table 3

C—O⋯π interactions (Å,°)

X	I	J	I⋯J	X⋯J	X—I⋯J
C15	O16	CgBiii	3.564 (2)	3.689 (2)	86.4 (1)

Symmetry code: (iii) . CgB is the centroid of the C1–C4/C12/C11 ring.