3-(2-Meth­oxy­naphthalen-1-yl)-2-benzofuran-1(3H)-one

Silambarasan, V.; Sundaramoorthy, S.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.; Velmurugan, D.

doi:10.1107/S1600536811026596

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1973

doi:10.1107/S1600536811026596

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3-(2-Methoxynaphthalen-1-yl)-2-benzofuran-1(3H)-one

V. Silambarasan,^a S. Sundaramoorthy,^a R. Sivasakthikumaran,^b A. K. Mohanakrishnan ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 21 June 2011; accepted 4 July 2011; online 9 July 2011)

The asymmetric unit of the title compound, C₁₉H₁₄O₃, contains two crystallographically independent molecules in which the dihedral angles between the naphthalene and benzofuran ring systems are 76.49 (7) and 86.17 (7)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen-bonding interactions into chains running parallel to the a axis. In addition, the crystal packing is stabilized by C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Howlett et al. (1999 ); Aslam et al. (2006 ); Galal et al. (2009 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ). For related structures see: Thenmozhi et al. (2010 ); Valerga et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₄O₃
M_r = 290.30
Monoclinic, P 2₁ /c
a = 13.2572 (5) Å
b = 11.8560 (4) Å
c = 18.6160 (7) Å
β = 91.657 (2)°
V = 2924.79 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.979, T_max = 0.982
27565 measured reflections
7292 independent reflections
4519 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.122
S = 1.00
7292 reflections
399 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O6ⁱ	0.93	2.45	3.238 (2)	142
C14—H14⋯O6ⁱⁱ	0.93	2.51	3.435 (2)	175
C12—H12⋯Cg4ⁱⁱ	0.98	2.93	3.755 (2)	143
C15—H15⋯Cg2ⁱⁱⁱ	0.93	2.88	3.800 (2)	169
C16—H16⋯Cg8^iv	0.93	2.81	3.553 (2)	137
C30—H30C⋯Cg8^v	0.96	2.89	3.687 (2)	141
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) -x+2, -y+1, -z; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026596/sj5168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026596/sj5168Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026596/sj5168Isup3.cml

checkCIF report

Comment top

Molecules containing a benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Galal et al., 2009). Compounds with the benzofuran skeleton (Akgul & Anil, 2003) show significant pharmacological activities such as fungicidal (Aslam et al., 2006), antitumor and antiviral activities (Galal et al., 2009). In order to get detailed information such as the geometrical features and the underlying interaction of the crystal structure, an X-ray study of the title compound was carried out.

Fig. 1 shows the asymmetric unit consisting of two molecules of the title compound. The naphthalene ring system is itself planar and the benzofuran ring system is also planar with a maximum deviation of 0.039 (1), 0.008 (1) Å, respectively in one molecule and 0.022 (2), 0.033 (1) Å in the other. The dihedral angles between the naphthalene ring systems and the benzofuran ring systems are 76.49 (7) and 86.17 (7)° in the two molecules. The C7—C8—O1—C11 [179.12 (15)°] and C29—C28—O4—C30 [179.87 (140)°] torsional angles that indicate the methoxy substitutions are essentially coplanar with the attached ring.

Hydrogen bond interactions are shown in Table 1 and the C—H···π interactions (Cg2, Cg4 and Cg8 are centriods of the rings containing the atoms C1—C6, C13—C18 and C20—C25 respectively). In the crystal structure, molecules are linked by intermolecular C—H···O hydrogen-bonding interactions into chains running parallel to the a axis.

Related literature top

For the biological activity of benzofuran compounds, see: Howlett et al. (1999); Aslam et al. (2006); Galal et al. (2009). For natural products with benzofuran rings, see: Akgul & Anil (2003). For related structures see: Thenmozhi et al. (2010); Valerga et al. (2009).

Experimental top

A mixture of 2-hydrazinopyridine and tolualdehyde were refluxed in ethanol with a catalytic quantity of conc. HCl or gl. AcOH. After the reaction is over, the contents were cooled down and the resulting product was filtered off. Diffraction quality crystals were obtained upon recrystallization in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A perspective view of the molecule showing the thermal ellipsoids drawn at the 30% probability level.
	Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. The crystal packing of the molecules is viewed down the b axis.

3-(2-Methoxynaphthalen-1-yl)-2-benzofuran-1(3H)-one top

Crystal data top

C₁₉H₁₄O₃	F(000) = 1216
M_r = 290.30	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1125 reflections
a = 13.2572 (5) Å	θ = 1.5–28.3°
b = 11.8560 (4) Å	µ = 0.09 mm⁻¹
c = 18.6160 (7) Å	T = 293 K
β = 91.657 (2)°	Block, colourless
V = 2924.79 (18) Å³	0.24 × 0.22 × 0.2 mm
Z = 8

Data collection top

Bruker SMART APEXII area-detector diffractometer	7292 independent reflections
Radiation source: fine-focus sealed tube	4519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
T_min = 0.979, T_max = 0.982	k = −15→12
27565 measured reflections	l = −24→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0514P)² + 0.4948P] where P = (F_o² + 2F_c²)/3
7292 reflections	(Δ/σ)_max = 0.001
399 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₉H₁₄O₃	V = 2924.79 (18) Å³
M_r = 290.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2572 (5) Å	µ = 0.09 mm⁻¹
b = 11.8560 (4) Å	T = 293 K
c = 18.6160 (7) Å	0.24 × 0.22 × 0.2 mm
β = 91.657 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	7292 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4519 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.982	R_int = 0.027
27565 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
7292 reflections	Δρ_min = −0.16 e Å⁻³
399 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
C1	0.41021 (11)	0.73457 (15)	0.18630 (8)	0.0555 (4)
H1	0.4191	0.6579	0.1781	0.067*
C2	0.34451 (13)	0.76890 (18)	0.23690 (9)	0.0676 (5)
H2	0.3092	0.7151	0.2624	0.081*
C3	0.32915 (14)	0.88307 (19)	0.25124 (10)	0.0734 (5)
H3	0.2832	0.9051	0.2854	0.088*
C4	0.38149 (14)	0.96087 (17)	0.21512 (10)	0.0691 (5)
H4	0.3718	1.0369	0.2251	0.083*
C5	0.45096 (11)	0.92985 (14)	0.16230 (8)	0.0518 (4)
C6	0.46531 (10)	0.81381 (12)	0.14591 (7)	0.0438 (3)
C7	0.53569 (10)	0.78300 (12)	0.09255 (8)	0.0428 (3)
C8	0.59224 (10)	0.86679 (13)	0.06143 (8)	0.0477 (4)
C9	0.57635 (12)	0.98140 (14)	0.07692 (9)	0.0560 (4)
H9	0.6129	1.0367	0.0536	0.067*
C10	0.50777 (13)	1.01078 (14)	0.12582 (10)	0.0604 (4)
H10	0.4978	1.0868	0.1357	0.072*
C11	0.72638 (15)	0.91029 (19)	−0.01797 (12)	0.0838 (6)
H11A	0.6843	0.9610	−0.0457	0.126*
H11B	0.7710	0.8714	−0.0493	0.126*
H11C	0.7653	0.9523	0.0171	0.126*
C12	0.55068 (10)	0.66110 (12)	0.07285 (8)	0.0459 (3)
H12	0.4906	0.6189	0.0865	0.055*
C13	0.57246 (10)	0.63310 (12)	−0.00365 (8)	0.0450 (3)
C14	0.51875 (12)	0.65709 (14)	−0.06670 (9)	0.0597 (4)
H14	0.4573	0.6948	−0.0664	0.072*
C15	0.56080 (16)	0.62235 (16)	−0.13052 (10)	0.0711 (5)
H15	0.5269	0.6381	−0.1738	0.085*
C16	0.65141 (15)	0.56512 (16)	−0.13148 (10)	0.0689 (5)
H16	0.6777	0.5437	−0.1752	0.083*
C17	0.70303 (13)	0.53953 (14)	−0.06901 (9)	0.0587 (4)
H17	0.7635	0.4999	−0.0693	0.070*
C18	0.66194 (10)	0.57481 (12)	−0.00517 (8)	0.0460 (3)
C19	0.70285 (11)	0.56471 (13)	0.06827 (9)	0.0514 (4)
O1	0.66568 (8)	0.83143 (10)	0.01706 (7)	0.0691 (3)
O2	0.63802 (8)	0.61512 (9)	0.11334 (5)	0.0532 (3)
O3	0.77989 (9)	0.52232 (11)	0.09071 (7)	0.0748 (4)
C20	1.22184 (12)	0.35822 (17)	0.29788 (9)	0.0630 (5)
H20	1.2703	0.3233	0.3274	0.076*
C21	1.20853 (13)	0.47138 (18)	0.30274 (9)	0.0662 (5)
H21	1.2475	0.5137	0.3352	0.079*
C22	1.13564 (13)	0.52358 (15)	0.25850 (9)	0.0599 (4)
H22	1.1268	0.6013	0.2614	0.072*
C23	1.07740 (12)	0.46323 (13)	0.21134 (8)	0.0521 (4)
H23	1.0291	0.5005	0.1829	0.063*
C24	1.08833 (10)	0.34463 (12)	0.20421 (7)	0.0438 (3)
C25	1.16370 (11)	0.29228 (14)	0.24895 (8)	0.0498 (4)
C26	1.17846 (12)	0.17547 (15)	0.24275 (9)	0.0592 (4)
H26	1.2266	0.1406	0.2725	0.071*
C27	1.12480 (12)	0.11230 (14)	0.19494 (9)	0.0578 (4)
H27	1.1372	0.0353	0.1914	0.069*
C28	1.05014 (11)	0.16302 (13)	0.15056 (8)	0.0479 (4)
C29	1.03008 (10)	0.27724 (12)	0.15521 (7)	0.0426 (3)
C30	1.01050 (15)	−0.01427 (14)	0.09473 (10)	0.0672 (5)
H30A	1.0780	−0.0264	0.0792	0.101*
H30B	0.9634	−0.0455	0.0600	0.101*
H30C	1.0021	−0.0504	0.1403	0.101*
C31	0.94556 (10)	0.32783 (12)	0.10989 (8)	0.0438 (3)
H31	0.9436	0.4090	0.1196	0.053*
C32	0.94656 (11)	0.31139 (12)	0.03025 (8)	0.0470 (3)
C33	1.02020 (14)	0.33418 (15)	−0.01830 (9)	0.0654 (5)
H33	1.0826	0.3631	−0.0035	0.079*
C34	0.9977 (2)	0.31242 (18)	−0.08992 (11)	0.0870 (7)
H34	1.0464	0.3260	−0.1239	0.104*
C35	0.9044 (2)	0.27095 (18)	−0.11231 (11)	0.0908 (7)
H35	0.8911	0.2583	−0.1610	0.109*
C36	0.83122 (17)	0.24824 (15)	−0.06370 (11)	0.0753 (6)
H36	0.7684	0.2203	−0.0784	0.090*
C37	0.85471 (12)	0.26858 (13)	0.00780 (9)	0.0529 (4)
C38	0.79453 (12)	0.24820 (13)	0.07115 (10)	0.0570 (4)
O4	0.99266 (9)	0.10388 (9)	0.10173 (6)	0.0598 (3)
O5	0.84930 (7)	0.27923 (9)	0.13030 (6)	0.0530 (3)
O6	0.71107 (9)	0.20914 (12)	0.07622 (9)	0.0861 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0534 (8)	0.0582 (10)	0.0553 (9)	−0.0061 (7)	0.0103 (7)	−0.0071 (8)
C2	0.0605 (10)	0.0846 (14)	0.0585 (11)	−0.0090 (9)	0.0161 (8)	−0.0075 (9)
C3	0.0623 (10)	0.0955 (16)	0.0631 (11)	0.0115 (10)	0.0165 (9)	−0.0168 (11)
C4	0.0679 (11)	0.0690 (12)	0.0706 (12)	0.0218 (9)	0.0060 (9)	−0.0158 (10)
C5	0.0497 (8)	0.0514 (10)	0.0540 (9)	0.0090 (7)	−0.0053 (7)	−0.0058 (7)
C6	0.0383 (7)	0.0485 (9)	0.0446 (8)	0.0014 (6)	−0.0024 (6)	−0.0043 (7)
C7	0.0382 (7)	0.0436 (8)	0.0466 (8)	−0.0014 (6)	0.0014 (6)	−0.0033 (6)
C8	0.0431 (7)	0.0516 (9)	0.0484 (8)	−0.0047 (6)	0.0024 (6)	−0.0012 (7)
C9	0.0593 (9)	0.0454 (10)	0.0630 (10)	−0.0071 (7)	−0.0045 (8)	0.0061 (8)
C10	0.0675 (10)	0.0441 (10)	0.0692 (11)	0.0072 (8)	−0.0053 (9)	−0.0030 (8)
C11	0.0716 (12)	0.0976 (16)	0.0834 (14)	−0.0200 (11)	0.0234 (10)	0.0152 (12)
C12	0.0412 (7)	0.0451 (9)	0.0519 (9)	−0.0031 (6)	0.0086 (6)	−0.0031 (7)
C13	0.0439 (7)	0.0404 (8)	0.0507 (8)	−0.0045 (6)	0.0027 (6)	−0.0043 (7)
C14	0.0568 (9)	0.0568 (11)	0.0648 (11)	−0.0010 (8)	−0.0115 (8)	−0.0046 (8)
C15	0.0952 (14)	0.0686 (12)	0.0487 (10)	−0.0125 (11)	−0.0121 (9)	−0.0042 (9)
C16	0.0913 (13)	0.0648 (12)	0.0513 (10)	−0.0121 (10)	0.0165 (9)	−0.0106 (9)
C17	0.0616 (9)	0.0530 (10)	0.0626 (11)	0.0007 (8)	0.0179 (8)	−0.0075 (8)
C18	0.0473 (7)	0.0413 (8)	0.0496 (8)	−0.0015 (6)	0.0068 (6)	−0.0016 (7)
C19	0.0528 (8)	0.0424 (9)	0.0590 (10)	0.0047 (7)	0.0019 (7)	0.0028 (7)
O1	0.0654 (7)	0.0627 (8)	0.0810 (8)	−0.0175 (6)	0.0313 (6)	−0.0063 (6)
O2	0.0633 (6)	0.0513 (7)	0.0452 (6)	0.0078 (5)	0.0023 (5)	0.0023 (5)
O3	0.0693 (8)	0.0728 (9)	0.0817 (9)	0.0253 (6)	−0.0110 (6)	0.0048 (7)
C20	0.0580 (9)	0.0837 (14)	0.0467 (9)	0.0084 (9)	−0.0081 (7)	0.0004 (9)
C21	0.0659 (10)	0.0841 (14)	0.0485 (10)	−0.0049 (9)	−0.0033 (8)	−0.0093 (9)
C22	0.0696 (10)	0.0568 (11)	0.0535 (10)	−0.0023 (8)	0.0024 (8)	−0.0047 (8)
C23	0.0569 (9)	0.0504 (10)	0.0489 (9)	0.0041 (7)	−0.0015 (7)	0.0031 (7)
C24	0.0441 (7)	0.0480 (9)	0.0395 (8)	0.0051 (6)	0.0071 (6)	0.0056 (6)
C25	0.0473 (8)	0.0619 (11)	0.0404 (8)	0.0101 (7)	0.0036 (6)	0.0051 (7)
C26	0.0572 (9)	0.0678 (12)	0.0524 (9)	0.0226 (8)	−0.0029 (7)	0.0102 (8)
C27	0.0640 (9)	0.0488 (10)	0.0608 (10)	0.0201 (8)	0.0034 (8)	0.0085 (8)
C28	0.0518 (8)	0.0446 (9)	0.0473 (8)	0.0074 (7)	0.0042 (7)	0.0040 (7)
C29	0.0435 (7)	0.0415 (8)	0.0429 (8)	0.0075 (6)	0.0037 (6)	0.0062 (6)
C30	0.0928 (13)	0.0409 (10)	0.0685 (11)	0.0084 (9)	0.0117 (10)	−0.0036 (8)
C31	0.0419 (7)	0.0379 (8)	0.0516 (9)	0.0027 (6)	0.0015 (6)	0.0049 (6)
C32	0.0528 (8)	0.0382 (8)	0.0501 (8)	0.0079 (6)	−0.0001 (7)	0.0091 (7)
C33	0.0729 (11)	0.0626 (12)	0.0615 (11)	0.0085 (9)	0.0119 (9)	0.0202 (9)
C34	0.1293 (19)	0.0723 (14)	0.0608 (13)	0.0321 (13)	0.0279 (13)	0.0245 (10)
C35	0.160 (2)	0.0598 (13)	0.0514 (12)	0.0322 (14)	−0.0157 (14)	0.0026 (10)
C36	0.1050 (15)	0.0499 (11)	0.0690 (13)	0.0135 (10)	−0.0301 (12)	−0.0001 (9)
C37	0.0610 (9)	0.0383 (8)	0.0587 (10)	0.0085 (7)	−0.0127 (8)	0.0035 (7)
C38	0.0469 (8)	0.0427 (9)	0.0810 (12)	0.0037 (7)	−0.0056 (8)	0.0076 (8)
O4	0.0742 (7)	0.0388 (6)	0.0659 (7)	0.0071 (5)	−0.0074 (6)	−0.0018 (5)
O5	0.0443 (5)	0.0545 (7)	0.0605 (7)	0.0050 (5)	0.0063 (5)	0.0078 (5)
O6	0.0511 (7)	0.0750 (9)	0.1318 (13)	−0.0123 (6)	−0.0054 (7)	0.0109 (8)

Geometric parameters (Å, º) top

C1—C2	1.363 (2)	C20—C21	1.356 (3)
C1—C6	1.419 (2)	C20—C25	1.412 (2)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.396 (3)	C21—C22	1.396 (2)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.346 (3)	C22—C23	1.356 (2)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.415 (2)	C23—C24	1.420 (2)
C4—H4	0.9300	C23—H23	0.9300
C5—C10	1.407 (2)	C24—C29	1.423 (2)
C5—C6	1.423 (2)	C24—C25	1.4245 (19)
C6—C7	1.4298 (19)	C25—C26	1.404 (2)
C7—C8	1.382 (2)	C26—C27	1.350 (2)
C7—C12	1.506 (2)	C26—H26	0.9300
C8—O1	1.3611 (18)	C27—C28	1.406 (2)
C8—C9	1.406 (2)	C27—H27	0.9300
C9—C10	1.351 (2)	C28—O4	1.3633 (18)
C9—H9	0.9300	C28—C29	1.383 (2)
C10—H10	0.9300	C29—C31	1.5075 (19)
C11—O1	1.406 (2)	C30—O4	1.4272 (18)
C11—H11A	0.9600	C30—H30A	0.9600
C11—H11B	0.9600	C30—H30B	0.9600
C11—H11C	0.9600	C30—H30C	0.9600
C12—O2	1.4681 (17)	C31—O5	1.4604 (16)
C12—C13	1.499 (2)	C31—C32	1.496 (2)
C12—H12	0.9800	C31—H31	0.9800
C13—C18	1.374 (2)	C32—C37	1.373 (2)
C13—C14	1.385 (2)	C32—C33	1.376 (2)
C14—C15	1.389 (2)	C33—C34	1.382 (3)
C14—H14	0.9300	C33—H33	0.9300
C15—C16	1.380 (3)	C34—C35	1.384 (3)
C15—H15	0.9300	C34—H34	0.9300
C16—C17	1.366 (3)	C35—C36	1.372 (3)
C16—H16	0.9300	C35—H35	0.9300
C17—C18	1.386 (2)	C36—C37	1.379 (2)
C17—H17	0.9300	C36—H36	0.9300
C18—C19	1.461 (2)	C37—C38	1.463 (2)
C19—O3	1.2023 (18)	C38—O6	1.2057 (19)
C19—O2	1.3570 (18)	C38—O5	1.352 (2)

C2—C1—C6	121.16 (16)	C21—C20—C25	121.40 (15)
C2—C1—H1	119.4	C21—C20—H20	119.3
C6—C1—H1	119.4	C25—C20—H20	119.3
C1—C2—C3	121.42 (18)	C20—C21—C22	119.22 (16)
C1—C2—H2	119.3	C20—C21—H21	120.4
C3—C2—H2	119.3	C22—C21—H21	120.4
C4—C3—C2	119.27 (17)	C23—C22—C21	121.29 (17)
C4—C3—H3	120.4	C23—C22—H22	119.4
C2—C3—H3	120.4	C21—C22—H22	119.4
C3—C4—C5	121.62 (17)	C22—C23—C24	121.67 (15)
C3—C4—H4	119.2	C22—C23—H23	119.2
C5—C4—H4	119.2	C24—C23—H23	119.2
C10—C5—C4	121.77 (16)	C23—C24—C29	124.11 (13)
C10—C5—C6	118.63 (14)	C23—C24—C25	116.65 (13)
C4—C5—C6	119.60 (16)	C29—C24—C25	119.24 (13)
C1—C6—C5	116.90 (13)	C26—C25—C20	121.63 (14)
C1—C6—C7	123.73 (14)	C26—C25—C24	118.61 (14)
C5—C6—C7	119.33 (13)	C20—C25—C24	119.76 (15)
C8—C7—C6	118.71 (13)	C27—C26—C25	121.96 (14)
C8—C7—C12	120.73 (13)	C27—C26—H26	119.0
C6—C7—C12	120.51 (12)	C25—C26—H26	119.0
O1—C8—C7	116.06 (14)	C26—C27—C28	119.92 (15)
O1—C8—C9	122.42 (14)	C26—C27—H27	120.0
C7—C8—C9	121.50 (14)	C28—C27—H27	120.0
C10—C9—C8	119.68 (15)	O4—C28—C29	116.14 (12)
C10—C9—H9	120.2	O4—C28—C27	122.84 (14)
C8—C9—H9	120.2	C29—C28—C27	121.02 (15)
C9—C10—C5	121.98 (16)	C28—C29—C24	119.20 (12)
C9—C10—H10	119.0	C28—C29—C31	119.71 (13)
C5—C10—H10	119.0	C24—C29—C31	121.06 (12)
O1—C11—H11A	109.5	O4—C30—H30A	109.5
O1—C11—H11B	109.5	O4—C30—H30B	109.5
H11A—C11—H11B	109.5	H30A—C30—H30B	109.5
O1—C11—H11C	109.5	O4—C30—H30C	109.5
H11A—C11—H11C	109.5	H30A—C30—H30C	109.5
H11B—C11—H11C	109.5	H30B—C30—H30C	109.5
O2—C12—C13	103.58 (11)	O5—C31—C32	103.85 (11)
O2—C12—C7	109.82 (11)	O5—C31—C29	109.78 (11)
C13—C12—C7	118.33 (12)	C32—C31—C29	118.36 (12)
O2—C12—H12	108.2	O5—C31—H31	108.1
C13—C12—H12	108.2	C32—C31—H31	108.1
C7—C12—H12	108.2	C29—C31—H31	108.1
C18—C13—C14	120.59 (14)	C37—C32—C33	120.82 (15)
C18—C13—C12	108.74 (13)	C37—C32—C31	108.46 (13)
C14—C13—C12	130.67 (14)	C33—C32—C31	130.70 (15)
C13—C14—C15	117.05 (16)	C32—C33—C34	117.35 (19)
C13—C14—H14	121.5	C32—C33—H33	121.3
C15—C14—H14	121.5	C34—C33—H33	121.3
C16—C15—C14	121.85 (17)	C33—C34—C35	121.5 (2)
C16—C15—H15	119.1	C33—C34—H34	119.2
C14—C15—H15	119.1	C35—C34—H34	119.2
C17—C16—C15	120.85 (16)	C36—C35—C34	120.91 (19)
C17—C16—H16	119.6	C36—C35—H35	119.5
C15—C16—H16	119.6	C34—C35—H35	119.5
C16—C17—C18	117.59 (16)	C35—C36—C37	117.3 (2)
C16—C17—H17	121.2	C35—C36—H36	121.4
C18—C17—H17	121.2	C37—C36—H36	121.4
C13—C18—C17	122.04 (15)	C32—C37—C36	122.13 (18)
C13—C18—C19	108.61 (13)	C32—C37—C38	108.36 (14)
C17—C18—C19	129.28 (14)	C36—C37—C38	129.49 (17)
O3—C19—O2	121.07 (15)	O6—C38—O5	120.88 (17)
O3—C19—C18	130.39 (15)	O6—C38—C37	130.50 (17)
O2—C19—C18	108.53 (12)	O5—C38—C37	108.61 (13)
C8—O1—C11	120.37 (14)	C28—O4—C30	118.35 (13)
C19—O2—C12	110.51 (11)	C38—O5—C31	110.37 (12)

C6—C1—C2—C3	−0.3 (3)	C25—C20—C21—C22	0.1 (3)
C1—C2—C3—C4	−1.0 (3)	C20—C21—C22—C23	0.6 (3)
C2—C3—C4—C5	0.7 (3)	C21—C22—C23—C24	−0.6 (2)
C3—C4—C5—C10	−178.27 (17)	C22—C23—C24—C29	−179.37 (14)
C3—C4—C5—C6	0.9 (3)	C22—C23—C24—C25	−0.2 (2)
C2—C1—C6—C5	1.9 (2)	C21—C20—C25—C26	178.79 (16)
C2—C1—C6—C7	179.56 (15)	C21—C20—C25—C24	−0.9 (2)
C10—C5—C6—C1	177.05 (14)	C23—C24—C25—C26	−178.81 (14)
C4—C5—C6—C1	−2.1 (2)	C29—C24—C25—C26	0.4 (2)
C10—C5—C6—C7	−0.8 (2)	C23—C24—C25—C20	0.9 (2)
C4—C5—C6—C7	−179.93 (14)	C29—C24—C25—C20	−179.88 (13)
C1—C6—C7—C8	−173.84 (13)	C20—C25—C26—C27	−178.43 (16)
C5—C6—C7—C8	3.8 (2)	C24—C25—C26—C27	1.2 (2)
C1—C6—C7—C12	3.8 (2)	C25—C26—C27—C28	−1.3 (3)
C5—C6—C7—C12	−178.57 (12)	C26—C27—C28—O4	−179.32 (15)
C6—C7—C8—O1	172.94 (12)	C26—C27—C28—C29	−0.3 (2)
C12—C7—C8—O1	−4.7 (2)	O4—C28—C29—C24	−178.96 (12)
C6—C7—C8—C9	−5.1 (2)	C27—C28—C29—C24	2.0 (2)
C12—C7—C8—C9	177.31 (13)	O4—C28—C29—C31	2.57 (19)
O1—C8—C9—C10	−174.67 (15)	C27—C28—C29—C31	−176.51 (13)
C7—C8—C9—C10	3.2 (2)	C23—C24—C29—C28	177.19 (14)
C8—C9—C10—C5	0.0 (2)	C25—C24—C29—C28	−2.0 (2)
C4—C5—C10—C9	177.98 (16)	C23—C24—C29—C31	−4.4 (2)
C6—C5—C10—C9	−1.2 (2)	C25—C24—C29—C31	176.45 (12)
C8—C7—C12—O2	81.43 (16)	C28—C29—C31—O5	63.33 (17)
C6—C7—C12—O2	−96.15 (14)	C24—C29—C31—O5	−115.11 (14)
C8—C7—C12—C13	−37.12 (19)	C28—C29—C31—C32	−55.56 (18)
C6—C7—C12—C13	145.30 (13)	C24—C29—C31—C32	126.00 (14)
O2—C12—C13—C18	1.35 (15)	O5—C31—C32—C37	5.82 (15)
C7—C12—C13—C18	123.12 (14)	C29—C31—C32—C37	127.76 (14)
O2—C12—C13—C14	−178.30 (15)	O5—C31—C32—C33	−175.73 (15)
C7—C12—C13—C14	−56.5 (2)	C29—C31—C32—C33	−53.8 (2)
C18—C13—C14—C15	−1.7 (2)	C37—C32—C33—C34	0.1 (2)
C12—C13—C14—C15	177.97 (15)	C31—C32—C33—C34	−178.20 (16)
C13—C14—C15—C16	0.8 (3)	C32—C33—C34—C35	0.9 (3)
C14—C15—C16—C17	0.6 (3)	C33—C34—C35—C36	−1.0 (3)
C15—C16—C17—C18	−1.1 (3)	C34—C35—C36—C37	0.1 (3)
C14—C13—C18—C17	1.2 (2)	C33—C32—C37—C36	−1.1 (2)
C12—C13—C18—C17	−178.54 (14)	C31—C32—C37—C36	177.56 (14)
C14—C13—C18—C19	178.39 (14)	C33—C32—C37—C38	177.33 (14)
C12—C13—C18—C19	−1.31 (16)	C31—C32—C37—C38	−4.03 (16)
C16—C17—C18—C13	0.3 (2)	C35—C36—C37—C32	1.0 (2)
C16—C17—C18—C19	−176.36 (16)	C35—C36—C37—C38	−177.07 (17)
C13—C18—C19—O3	−178.41 (17)	C32—C37—C38—O6	−178.17 (17)
C17—C18—C19—O3	−1.4 (3)	C36—C37—C38—O6	0.1 (3)
C13—C18—C19—O2	0.74 (17)	C32—C37—C38—O5	0.50 (17)
C17—C18—C19—O2	177.71 (15)	C36—C37—C38—O5	178.75 (15)
C7—C8—O1—C11	179.12 (15)	C29—C28—O4—C30	179.87 (14)
C9—C8—O1—C11	−2.9 (2)	C27—C28—O4—C30	−1.1 (2)
O3—C19—O2—C12	179.41 (14)	O6—C38—O5—C31	−177.81 (14)
C18—C19—O2—C12	0.16 (16)	C37—C38—O5—C31	3.38 (16)
C13—C12—O2—C19	−0.90 (15)	C32—C31—O5—C38	−5.60 (14)
C7—C12—O2—C19	−128.20 (12)	C29—C31—O5—C38	−133.08 (12)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O6ⁱ	0.93	2.45	3.238 (2)	142
C14—H14···O6ⁱⁱ	0.93	2.51	3.435 (2)	175
C12—H12···Cg4ⁱⁱ	0.98	2.93	3.755 (2)	143
C15—H15···Cg2ⁱⁱⁱ	0.93	2.88	3.800 (2)	169
C16—H16···Cg8^iv	0.93	2.81	3.553 (2)	137
C30—H30C···Cg8^v	0.96	2.89	3.687 (2)	141

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−3/2; (iv) −x+2, −y+1, −z; (v) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄O₃
M_r	290.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.2572 (5), 11.8560 (4), 18.6160 (7)
β (°)	91.657 (2)
V (Å³)	2924.79 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.22 × 0.2

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.979, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	27565, 7292, 4519
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.122, 1.00
No. of reflections	7292
No. of parameters	399
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O6ⁱ	0.93	2.45	3.238 (2)	142
C14—H14···O6ⁱⁱ	0.93	2.51	3.435 (2)	175
C12—H12···Cg4ⁱⁱ	0.98	2.93	3.755 (2)	143
C15—H15···Cg2ⁱⁱⁱ	0.93	2.88	3.800 (2)	169
C16—H16···Cg8^iv	0.93	2.81	3.553 (2)	137
C30—H30C···Cg8^v	0.96	2.89	3.687 (2)	141

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−3/2; (iv) −x+2, −y+1, −z; (v) −x+2, y−1/2, −z+1/2.

Acknowledgements

SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

References

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Volume 67| Part 8| August 2011| Page o1973

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