Crystal structure of 3-[4-(benz­yloxy)phen­yl]-2,3-di­hydro-1H-benzo[f]chromen-1-one

Vasanthi, R.; Reuben Jonathan, D.; Ezhilarasi, K.S.; Sathya, S.; Usha, G.

doi:10.1107/S1600536814020868

organic compounds

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1116-o1117

doi:10.1107/S1600536814020868

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Crystal structure of 3-[4-(benzyloxy)phenyl]-2,3-dihydro-1H-benzo[f]chromen-1-one

R. Vasanthi,^a D. Reuben Jonathan,^b K. S. Ezhilarasi,^a S. Sathya ^a and G. Usha ^a ^*

^aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Chemistry, Madras Christian College, Chennai-59, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 12 September 2014; accepted 17 September 2014; online 20 September 2014)

In the title compound, C₂₆H₂₀O₃, the pyran ring has a distorted half-chair conformation and its mean plane is inclined to the naphthalene ring system, to which it is fused, by 10.79 (9)°. The dihedral angles between the napthalene unit and the benzene and phenyl rings are 54.39 (9) and 52.65 (12)°, respectively, while the benzene and phenyl rings are inclined to one another by 74.80 (14)°. There is a short C—H⋯O contact in the chromen-1-one unit. In the crystal, molecules are linked by two pairs of C—H⋯O hydrogen bonds, forming inversion dimers described by graph set motifs R₂²(8) and R₂²(10), giving rise to chains running parallel to (101). The chains are linked via C—H⋯π interactions, forming sheets lying parallel to (010).

Keywords: crystal structure; flavone; chalcone; chromenone; C—H⋯O hydrogen bonding.

CCDC reference: 1024680

1. Related literature

For the biological activity of flavone derivatives, see: Thomas et al. (2013 ); Kumar et al. (2014 ); Lee et al. (2014 ). For the synthesis of the title compound, see: Kumar et al. (2014).

2. Experimental

2.1. Crystal data

C₂₆H₁₉O₃
M_r = 379.41
Monoclinic, P 2₁ /n
a = 6.9632 (4) Å
b = 35.846 (2) Å
c = 7.7879 (5) Å
β = 100.375 (3)°
V = 1912.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.971, T_max = 0.979
26372 measured reflections
3956 independent reflections
2814 reflections with I > 2σ(I)
R_int = 0.067

2.3. Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.172
S = 0.98
3956 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of rings C1–C6 and C14–C19, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3ⁱ	0.93	2.50	3.342 (3)	150
C13—H13⋯O2ⁱⁱ	0.98	2.51	3.314 (3)	140
C7—H7⋯Cg4ⁱ	0.93	2.96	3.688 (2)	136
C16—H16⋯Cg2ⁱⁱⁱ	0.93	2.90	3.602 (2)	133
C19—H19⋯Cg2^iv	0.93	2.97	3.593 (2)	126
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1; (iv) -x+2, -y, -z+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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1024680

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814020868/su2785sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814020868/su2785Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814020868/su2785Isup3.cml

checkCIF report

Related literature top

For the biological activity of flavone derivatives, see: Thomas et al. (2013); Kumar et al. (2014); Lee et al. (2014). For the synthesis of the title compound, see: Kumar et al. (2014).

Experimental top

The title compound was synthesized following the reported procedure (Kumar et al., 2014). The crude product produced was recrystallized twice from chloroform yielding block-like colourless crystals.

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 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing viewed along the a axis of the title compound. The dashed lines indicate the hydrogen bonds (see Table 1 for details).

3-[4-(Benzyloxy)phenyl]-2,3-dihydro-1H-benzo[f]chromen-1-one top

Crystal data top

C₂₆H₁₉O₃	Z = 4
M_r = 379.41	F(000) = 796.0
Monoclinic, P2₁/n	D_x = 1.318 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.9632 (4) Å	Cell parameters from 3956 reflections
b = 35.846 (2) Å	µ = 0.09 mm⁻¹
c = 7.7879 (5) Å	T = 293 K
β = 100.375 (3)°	Block, colourless
V = 1912.1 (2) Å³	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	3956 independent reflections
Radiation source: fine-focus sealed tube	2814 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ω and ϕ scan	θ_max = 26.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
T_min = 0.971, T_max = 0.979	k = −44→44
26372 measured reflections	l = −8→9

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0897P)² + 0.9692P] where P = (F_o² + 2F_c²)/3
3956 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₆H₁₉O₃	V = 1912.1 (2) Å³
M_r = 379.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9632 (4) Å	µ = 0.09 mm⁻¹
b = 35.846 (2) Å	T = 293 K
c = 7.7879 (5) Å	0.35 × 0.30 × 0.25 mm
β = 100.375 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3956 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2814 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.979	R_int = 0.067
26372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 0.98	Δρ_max = 0.56 e Å⁻³
3956 reflections	Δρ_min = −0.45 e Å⁻³
262 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
C22	0.0790 (5)	0.22907 (8)	0.9025 (5)	0.0828 (10)
H22	0.0911	0.2093	0.9810	0.099*
C23	0.0400 (6)	0.26438 (9)	0.9588 (5)	0.0856 (10)
H23	0.0287	0.2683	1.0746	0.103*
C25	0.0388 (5)	0.28758 (8)	0.6783 (5)	0.0820 (10)
H25	0.0254	0.3075	0.6004	0.098*
C1	0.9499 (3)	−0.06874 (5)	0.7729 (3)	0.0373 (5)
C2	1.1154 (3)	−0.08336 (6)	0.7143 (3)	0.0450 (5)
H2	1.2012	−0.0671	0.6736	0.054*
C3	1.1523 (4)	−0.12073 (7)	0.7161 (3)	0.0543 (6)
H3	1.2610	−0.1295	0.6746	0.065*
C4	1.0296 (4)	−0.14605 (6)	0.7791 (3)	0.0568 (7)
H4	1.0565	−0.1715	0.7800	0.068*
C5	0.8703 (4)	−0.13318 (6)	0.8392 (3)	0.0514 (6)
H5	0.7891	−0.1500	0.8822	0.062*
C6	0.8258 (3)	−0.09490 (6)	0.8376 (3)	0.0412 (5)
C7	0.6594 (3)	−0.08175 (6)	0.8992 (3)	0.0482 (6)
H7	0.5810	−0.0987	0.9451	0.058*
C8	0.6111 (3)	−0.04520 (6)	0.8932 (3)	0.0465 (5)
H8	0.5002	−0.0373	0.9338	0.056*
C9	0.7292 (3)	−0.01921 (6)	0.8251 (3)	0.0375 (5)
C10	0.8997 (3)	−0.02972 (5)	0.7698 (3)	0.0344 (4)
C11	1.0247 (3)	0.00040 (6)	0.7191 (3)	0.0364 (5)
C12	0.9490 (3)	0.03946 (6)	0.7283 (3)	0.0408 (5)
H12	1.0277	0.0604	0.7525	0.049*
C13	0.7290 (3)	0.04024 (5)	0.6933 (3)	0.0373 (5)
H13	0.6829	0.0297	0.5770	0.045*
C14	0.6330 (3)	0.07754 (5)	0.7027 (3)	0.0371 (5)
C15	0.4393 (3)	0.08196 (6)	0.6255 (3)	0.0481 (6)
H15	0.3734	0.0620	0.5656	0.058*
C16	0.3404 (3)	0.11518 (6)	0.6346 (3)	0.0498 (6)
H16	0.2101	0.1173	0.5815	0.060*
C17	0.4364 (3)	0.14510 (5)	0.7228 (3)	0.0400 (5)
C18	0.6314 (3)	0.14146 (6)	0.7982 (3)	0.0507 (6)
H18	0.6982	0.1617	0.8553	0.061*
C19	0.7269 (3)	0.10812 (6)	0.7892 (3)	0.0492 (6)
H19	0.8573	0.1060	0.8422	0.059*
C20	0.1518 (4)	0.18447 (7)	0.6774 (4)	0.0630 (7)
H20A	0.0746	0.1657	0.7234	0.076*
H20B	0.1266	0.1827	0.5510	0.076*
C21	0.1004 (3)	0.22258 (6)	0.7340 (4)	0.0529 (6)
C24	0.0182 (4)	0.29332 (7)	0.8453 (5)	0.0685 (8)
H24	−0.0108	0.3170	0.8822	0.082*
C26	0.0797 (5)	0.25237 (8)	0.6224 (4)	0.0744 (9)
H26	0.0935	0.2489	0.5070	0.089*
O1	0.3549 (2)	0.17907 (4)	0.7444 (2)	0.0519 (4)
O2	1.1831 (2)	−0.00482 (4)	0.6780 (2)	0.0514 (4)
O3	0.6623 (2)	0.01632 (4)	0.8212 (2)	0.0444 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C22	0.116 (3)	0.0570 (18)	0.085 (2)	0.0332 (17)	0.042 (2)	0.0208 (15)
C23	0.116 (3)	0.072 (2)	0.076 (2)	0.0312 (19)	0.036 (2)	0.0007 (16)
C25	0.106 (3)	0.0529 (17)	0.093 (3)	0.0263 (16)	0.034 (2)	0.0219 (16)
C1	0.0407 (11)	0.0366 (11)	0.0335 (11)	0.0028 (8)	0.0035 (9)	−0.0002 (8)
C2	0.0477 (13)	0.0410 (12)	0.0466 (13)	0.0067 (9)	0.0088 (10)	0.0024 (10)
C3	0.0565 (14)	0.0479 (14)	0.0575 (15)	0.0153 (11)	0.0076 (12)	−0.0022 (11)
C4	0.0704 (17)	0.0349 (12)	0.0602 (16)	0.0083 (11)	−0.0015 (13)	−0.0017 (11)
C5	0.0586 (15)	0.0365 (12)	0.0555 (15)	−0.0049 (10)	0.0009 (12)	0.0033 (10)
C6	0.0447 (12)	0.0372 (11)	0.0396 (12)	−0.0039 (9)	0.0016 (9)	0.0034 (9)
C7	0.0489 (13)	0.0425 (13)	0.0553 (14)	−0.0072 (10)	0.0148 (11)	0.0086 (10)
C8	0.0433 (12)	0.0494 (13)	0.0506 (13)	0.0003 (10)	0.0183 (10)	0.0058 (10)
C9	0.0409 (11)	0.0353 (11)	0.0378 (11)	0.0007 (8)	0.0108 (9)	0.0011 (8)
C10	0.0369 (10)	0.0356 (10)	0.0313 (10)	0.0016 (8)	0.0079 (8)	0.0023 (8)
C11	0.0360 (11)	0.0389 (11)	0.0347 (11)	0.0008 (8)	0.0077 (8)	0.0019 (8)
C12	0.0389 (11)	0.0337 (11)	0.0507 (13)	−0.0011 (8)	0.0109 (9)	0.0012 (9)
C13	0.0411 (11)	0.0344 (11)	0.0379 (11)	0.0008 (8)	0.0110 (9)	0.0015 (8)
C14	0.0396 (11)	0.0359 (11)	0.0371 (11)	0.0028 (8)	0.0099 (9)	0.0001 (8)
C15	0.0471 (13)	0.0356 (12)	0.0585 (15)	0.0005 (9)	0.0010 (11)	−0.0072 (10)
C16	0.0422 (12)	0.0426 (13)	0.0608 (15)	0.0060 (9)	−0.0008 (11)	−0.0040 (11)
C17	0.0469 (12)	0.0311 (10)	0.0430 (12)	0.0051 (9)	0.0106 (10)	0.0023 (8)
C18	0.0493 (13)	0.0392 (12)	0.0602 (15)	−0.0005 (10)	0.0011 (11)	−0.0102 (10)
C19	0.0400 (12)	0.0430 (13)	0.0615 (16)	0.0045 (9)	0.0010 (10)	−0.0060 (10)
C20	0.0506 (14)	0.0508 (15)	0.083 (2)	0.0120 (11)	0.0008 (13)	−0.0111 (13)
C21	0.0452 (13)	0.0426 (13)	0.0702 (17)	0.0091 (10)	0.0090 (12)	−0.0011 (11)
C24	0.0710 (18)	0.0450 (15)	0.093 (2)	0.0124 (12)	0.0234 (16)	−0.0042 (14)
C26	0.094 (2)	0.0689 (19)	0.0622 (18)	0.0301 (16)	0.0193 (16)	0.0089 (14)
O1	0.0497 (9)	0.0351 (8)	0.0694 (11)	0.0092 (7)	0.0063 (8)	−0.0039 (7)
O2	0.0432 (9)	0.0484 (9)	0.0678 (11)	0.0025 (7)	0.0236 (8)	0.0018 (8)
O3	0.0485 (9)	0.0363 (8)	0.0545 (10)	0.0070 (6)	0.0256 (7)	0.0050 (7)

Geometric parameters (Å, º) top

C22—C21	1.367 (4)	C10—C11	1.484 (3)
C22—C23	1.383 (4)	C11—O2	1.218 (2)
C22—H22	0.9300	C11—C12	1.502 (3)
C23—C24	1.353 (4)	C12—C13	1.507 (3)
C23—H23	0.9300	C12—H12	0.9300
C25—C24	1.350 (5)	C13—O3	1.453 (2)
C25—C26	1.381 (4)	C13—C14	1.503 (3)
C25—H25	0.9300	C13—H13	0.9800
C1—C2	1.414 (3)	C14—C15	1.384 (3)
C1—C6	1.428 (3)	C14—C19	1.387 (3)
C1—C10	1.441 (3)	C15—C16	1.384 (3)
C2—C3	1.364 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.380 (3)
C3—C4	1.394 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—O1	1.367 (2)
C4—C5	1.360 (4)	C17—C18	1.385 (3)
C4—H4	0.9300	C18—C19	1.376 (3)
C5—C6	1.406 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.412 (3)	C20—O1	1.430 (3)
C7—C8	1.352 (3)	C20—C21	1.499 (3)
C7—H7	0.9300	C20—H20A	0.9700
C8—C9	1.408 (3)	C20—H20B	0.9700
C8—H8	0.9300	C21—C26	1.368 (4)
C9—O3	1.355 (2)	C24—H24	0.9300
C9—C10	1.386 (3)	C26—H26	0.9300

C21—C22—C23	121.5 (3)	C11—C12—H12	124.4
C21—C22—H22	119.3	C13—C12—H12	124.4
C23—C22—H22	119.3	O3—C13—C14	106.96 (15)
C24—C23—C22	120.0 (3)	O3—C13—C12	107.76 (16)
C24—C23—H23	120.0	C14—C13—C12	117.02 (17)
C22—C23—H23	120.0	O3—C13—H13	108.3
C24—C25—C26	120.4 (3)	C14—C13—H13	108.3
C24—C25—H25	119.8	C12—C13—H13	108.3
C26—C25—H25	119.8	C15—C14—C19	117.26 (19)
C2—C1—C6	116.79 (19)	C15—C14—C13	119.22 (18)
C2—C1—C10	124.30 (19)	C19—C14—C13	123.50 (19)
C6—C1—C10	118.91 (19)	C14—C15—C16	122.1 (2)
C3—C2—C1	121.6 (2)	C14—C15—H15	118.9
C3—C2—H2	119.2	C16—C15—H15	118.9
C1—C2—H2	119.2	C17—C16—C15	119.6 (2)
C2—C3—C4	121.1 (2)	C17—C16—H16	120.2
C2—C3—H3	119.4	C15—C16—H16	120.2
C4—C3—H3	119.4	O1—C17—C16	125.4 (2)
C5—C4—C3	119.3 (2)	O1—C17—C18	115.40 (19)
C5—C4—H4	120.3	C16—C17—C18	119.21 (19)
C3—C4—H4	120.3	C19—C18—C17	120.4 (2)
C4—C5—C6	121.3 (2)	C19—C18—H18	119.8
C4—C5—H5	119.3	C17—C18—H18	119.8
C6—C5—H5	119.3	C18—C19—C14	121.4 (2)
C5—C6—C7	121.0 (2)	C18—C19—H19	119.3
C5—C6—C1	119.8 (2)	C14—C19—H19	119.3
C7—C6—C1	119.11 (19)	O1—C20—C21	106.8 (2)
C8—C7—C6	121.8 (2)	O1—C20—H20A	110.4
C8—C7—H7	119.1	C21—C20—H20A	110.4
C6—C7—H7	119.1	O1—C20—H20B	110.4
C7—C8—C9	119.7 (2)	C21—C20—H20B	110.4
C7—C8—H8	120.1	H20A—C20—H20B	108.6
C9—C8—H8	120.1	C26—C21—C22	117.4 (2)
O3—C9—C10	123.98 (18)	C26—C21—C20	121.9 (3)
O3—C9—C8	114.13 (18)	C22—C21—C20	120.7 (2)
C10—C9—C8	121.89 (19)	C23—C24—C25	119.6 (3)
C9—C10—C1	118.51 (18)	C23—C24—H24	120.2
C9—C10—C11	117.45 (17)	C25—C24—H24	120.2
C1—C10—C11	123.97 (18)	C21—C26—C25	121.1 (3)
O2—C11—C10	124.10 (18)	C21—C26—H26	119.4
O2—C11—C12	119.87 (18)	C25—C26—H26	119.4
C10—C11—C12	115.97 (17)	C17—O1—C20	118.75 (18)
C11—C12—C13	111.26 (17)	C9—O3—C13	114.78 (15)

C21—C22—C23—C24	1.3 (6)	C11—C12—C13—C14	178.52 (17)
C6—C1—C2—C3	1.4 (3)	O3—C13—C14—C15	−77.2 (2)
C10—C1—C2—C3	−178.2 (2)	C12—C13—C14—C15	161.9 (2)
C1—C2—C3—C4	−1.2 (4)	O3—C13—C14—C19	101.1 (2)
C2—C3—C4—C5	0.2 (4)	C12—C13—C14—C19	−19.8 (3)
C3—C4—C5—C6	0.6 (4)	C19—C14—C15—C16	−0.7 (4)
C4—C5—C6—C7	179.6 (2)	C13—C14—C15—C16	177.7 (2)
C4—C5—C6—C1	−0.4 (3)	C14—C15—C16—C17	0.1 (4)
C2—C1—C6—C5	−0.6 (3)	C15—C16—C17—O1	−178.6 (2)
C10—C1—C6—C5	178.97 (19)	C15—C16—C17—C18	1.1 (4)
C2—C1—C6—C7	179.5 (2)	O1—C17—C18—C19	178.1 (2)
C10—C1—C6—C7	−1.0 (3)	C16—C17—C18—C19	−1.7 (4)
C5—C6—C7—C8	−177.8 (2)	C17—C18—C19—C14	1.1 (4)
C1—C6—C7—C8	2.2 (3)	C15—C14—C19—C18	0.1 (4)
C6—C7—C8—C9	−0.4 (4)	C13—C14—C19—C18	−178.2 (2)
C7—C8—C9—O3	178.1 (2)	C23—C22—C21—C26	−0.6 (5)
C7—C8—C9—C10	−2.7 (3)	C23—C22—C21—C20	177.2 (3)
O3—C9—C10—C1	−177.06 (19)	O1—C20—C21—C26	102.0 (3)
C8—C9—C10—C1	3.8 (3)	O1—C20—C21—C22	−75.7 (3)
O3—C9—C10—C11	5.9 (3)	C22—C23—C24—C25	−1.3 (6)
C8—C9—C10—C11	−173.2 (2)	C26—C25—C24—C23	0.7 (5)
C2—C1—C10—C9	177.6 (2)	C22—C21—C26—C25	0.0 (5)
C6—C1—C10—C9	−1.9 (3)	C20—C21—C26—C25	−177.8 (3)
C2—C1—C10—C11	−5.6 (3)	C24—C25—C26—C21	0.0 (5)
C6—C1—C10—C11	174.91 (19)	C16—C17—O1—C20	2.6 (3)
C9—C10—C11—O2	175.6 (2)	C18—C17—O1—C20	−177.1 (2)
C1—C10—C11—O2	−1.3 (3)	C21—C20—O1—C17	175.0 (2)
C9—C10—C11—C12	−1.8 (3)	C10—C9—O3—C13	24.6 (3)
C1—C10—C11—C12	−178.61 (19)	C8—C9—O3—C13	−156.19 (19)
O2—C11—C12—C13	152.1 (2)	C14—C13—O3—C9	177.39 (17)
C10—C11—C12—C13	−30.4 (2)	C12—C13—O3—C9	−56.0 (2)
C11—C12—C13—O3	58.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of rings C1–C6 and C14–C19, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3ⁱ	0.93	2.50	3.342 (3)	150
C13—H13···O2ⁱⁱ	0.98	2.51	3.314 (3)	140
C7—H7···Cg4ⁱ	0.93	2.96	3.688 (2)	136
C16—H16···Cg2ⁱⁱⁱ	0.93	2.90	3.602 (2)	133
C19—H19···Cg2^iv	0.93	2.97	3.593 (2)	126

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of rings C1–C6 and C14–C19, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3ⁱ	0.93	2.50	3.342 (3)	150
C13—H13···O2ⁱⁱ	0.98	2.51	3.314 (3)	140
C7—H7···Cg4ⁱ	0.93	2.96	3.688 (2)	136
C16—H16···Cg2ⁱⁱⁱ	0.93	2.90	3.602 (2)	133
C19—H19···Cg2^iv	0.93	2.97	3.593 (2)	126

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

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kumar, B., Kumari, B., Singh, N., Ram, B. & Balram, B. (2014). J. Appl. Chem. 3, 1468–1474. CAS Google Scholar
Lee, M. S., Yong, Y., Lee, J. M., Koh, D., Shin, S. Y. & Lee, Y. H. (2014). Biol. Chem. 57, 129–132. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, N. & Zachariah, S. M. (2013). Asian J. Pharm. Clin. Res. 6, Suppl. 2, 11–15. Google Scholar

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Volume 70| Part 10| October 2014| Pages o1116-o1117

doi:10.1107/S1600536814020868

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

Crystal structure of 3-[4-(benz­yl­oxy)phen­yl]-2,3-di­hydro-1H-benzo[f]chromen-1-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3-[4-(benzyloxy)phenyl]-2,3-dihydro-1H-benzo[f]chromen-1-one