2-Phenyl-5,7-bis­(prop-2-en-1-yl­oxy)-4H-chromen-4-one

Nallasivam, A.; Nethaji, M.; Vembu, N.; Ragunathan, V.; Sulochana, N.

doi:10.1107/S1600536808039743

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o1

doi:10.1107/S1600536808039743

Open

access

2-Phenyl-5,7-bis(prop-2-en-1-yloxy)-4H-chromen-4-one

Angannan Nallasivam,^a Munirathinam Nethaji,^b Nagarajan Vembu,^c ^* Venkatraman Ragunathan ^d and Nagarajan Sulochana ^a

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India, ^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and ^dDepartment of Chemistry, Kandasamy Kandar College, Velur 638 182, India
^*Correspondence e-mail: vembu57@yahoo.com

(Received 6 November 2008; accepted 25 November 2008; online 3 December 2008)

In the title compound, C₂₁H₁₈O₄, tthe dihedral angle between the chromene ring system and the pendant phenyl ring is 6.1 (1)°. The crystal structure is stabilized by an intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the biological and pharmacological properties of benzopyrans and their derivatives, see Brooks (1998 ); Hatakeyama et al. (1988 ); Hyana & Saimoto (1987 ); Tang et al. (2007 ). For a detailed account of the importance of 4H-chromenes, see Liu et al. (2007 ); Wang, Fang et al. (2003 ); Wang, Zhang et al. (2003 ). For hydrogen-bonding interactions and motifs, see: Bernstein et al. (1995 ); Desiraju (1989 ); Desiraju & Steiner (1999 ); Etter (1990 ).

Experimental

Crystal data

C₂₁H₁₈O₄
M_r = 334.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.299 (2) Å
b = 15.798 (6) Å
c = 17.429 (6) Å
V = 1734.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.35 × 0.32 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.969, T_max = 0.975
13979 measured reflections
2055 independent reflections
1793 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.098
S = 1.01
2055 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯O11ⁱ	0.97	2.51	3.229 (4)	131
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SMART; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039743/fb2126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039743/fb2126Isup2.hkl

checkCIF report

Comment top

Chromenes (benzopyrans) and their derivatives have numerous biological and pharmacological properties (Tang et al., 2007) such as antisterility (Brooks, 1998) and anticancer activity (Hyana & Saimoto, 1987). In addition, polyfunctional chromene units are present in numerous natural products (Hatakeyama et al., 1988). 4H-chromenes are important synthons for some natural products (Liu et al., 2007). As a part of our structural investigations on 4H-chromene derivatives, the single-crystal X-ray diffraction study on the title compound was carried out.

The chromene ring is almost planar: The puckering amplitude of the chromene ring is 0.097 (3) Å. In the related chromene derivatives (Wang, Zhang et al., 2003; Wang, Fang et al., 2003), the chromene ring is also planar. In the title structure, the interplanar angle between the chromene ring and the 2-phenyl ring is 6.1 (1)° thereby indicating their almost coplanar arrangement (Fig. 1). The propenyloxy substituents at both C5 and C7 are coplanar with the chromene ring with the respective interplanar angles 1.7 (2)° and 8.8 (2)°.

The crystal structure is stabilized by the interplay of C–H···O and C–H···π interactions (Fig. 2, Table 1; Desiraju & Steiner, 1999; Desiraju, 1989). Each of C15–H15A···O12, C19–H19A···O16 and C25–H25···O1 interactions are involved in the S(5) motifs (Bernstein et al., 1995; Etter, 1990).

Related literature top

For the biological and pharmacological properties of benzopyrans and their derivatives, see Brooks (1998); Hatakeyama et al. (1988); Hyana & Saimoto (1987); Tang et al. (2007). For a detailed account of the importance of 4H-chromenes, see Liu et al. (2007); Wang, Fang et al. (2003); Wang, Zhang et al. (2003). For polyfunctional chromene units in natural products, see: Hatakeyema et al. (1988). For hydrogen-bonding interactions and motifs, see: Bernstein et al. (1995); Desiraju (1989); Desiraju & Steiner (1999); Etter (1990);

Experimental top

A suspension of chrysin (3.93 mmol, 1.00 g) and potassium carbonate (11.81 mmol, 1.64 g) in dimethyl formamide (10 ml) were added into a round bottom flask. The reaction mixture was heated to 383 K for 2–3 h. The reaction mixture was then cooled to 333 K and allyl bromide (15.74 mmol, 1.90 g) was slowly added to the reaction mixture with the help of a dropping funnel. The reaction mixture was maintained for 8–9 h at 333 K and monitored by high pressure liquid chromatography (HPLC). After completion of the reaction, the content was quenched with water and stirred for 30–45 min at 303 K. T he obtained crude solid was filtered and washed with plenty of water followed by methanol and dried under vacuum at 343 K. The compound was purified by column chromatography using ethyl acetate/n-hexane (1:1) as eluent. All highly pure column fractions were concentrated in a rota evaporator. The dried compound was dissolved in dichloromethane/hexane (1:1) mixture (10 ml). The clear solution was kept for a week and the resulting needle shaped crystals of average size 0.3 mm were washed with n-hexane. The crystals were dried over high vacuum at 343–348 K. Yield: 90%

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule showing the displacement ellipsoids depicted at the 50% probability level for all non-H atoms. The hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The molecular packing viewed down the c-axis. Dashed lines represent weak C–H···O interactions.

2-Phenyl-5,7-bis(prop-2-en-1-yloxy)-4H-chromen-4-one top

Crystal data top

C₂₁H₁₈O₄	D_x = 1.281 Mg m⁻³
M_r = 334.35	Melting point = 434–437 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 576 reflections
a = 6.299 (2) Å	θ = 1.8–26.0°
b = 15.798 (6) Å	µ = 0.09 mm⁻¹
c = 17.429 (6) Å	T = 293 K
V = 1734.3 (11) Å³	Needle, colourless
Z = 4	0.35 × 0.32 × 0.29 mm
F(000) = 704

Data collection top

Bruker SMART APEX CCD diffractometer	3543 independent reflections
Radiation source: fine-focus sealed tube	1793 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 0.3 pixels mm^-1	θ_max = 26.4°, θ_min = 1.7°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	k = −19→19
T_min = 0.969, T_max = 0.975	l = −21→20
13979 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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0343P)² + 0.1512P] where P = (F_o² + 2F_c²)/3
2055 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³
72 constraints

Crystal data top

C₂₁H₁₈O₄	V = 1734.3 (11) Å³
M_r = 334.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.299 (2) Å	µ = 0.09 mm⁻¹
b = 15.798 (6) Å	T = 293 K
c = 17.429 (6) Å	0.35 × 0.32 × 0.29 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3543 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	1793 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.975	R_int = 0.062
13979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	Δρ_max = 0.10 e Å⁻³
2055 reflections	Δρ_min = −0.10 e Å⁻³
226 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
O1	0.4396 (4)	1.06971 (12)	0.13245 (11)	0.0650 (6)
C2	0.5860 (6)	1.0832 (2)	0.0765 (2)	0.0639 (8)
C3	0.5782 (6)	1.0403 (2)	0.0102 (2)	0.0745 (9)
H3	0.6761	1.0541	−0.0278	0.089*
C4	0.4277 (6)	0.9746 (2)	−0.0056 (2)	0.0696 (9)
C5	0.0891 (6)	0.90891 (19)	0.04852 (18)	0.0608 (8)
C6	−0.0584 (6)	0.90372 (18)	0.10630 (18)	0.0622 (8)
H6	−0.1728	0.8668	0.1020	0.075*
C7	−0.0358 (6)	0.95419 (19)	0.17160 (18)	0.0590 (8)
C8	0.1332 (5)	1.00863 (19)	0.17997 (18)	0.0610 (9)
H8	0.1495	1.0414	0.2239	0.073*
C9	0.2778 (5)	1.01254 (18)	0.12026 (18)	0.0557 (8)
C10	0.2641 (5)	0.96435 (18)	0.05336 (17)	0.0559 (8)
O11	0.4392 (5)	0.93093 (17)	−0.06419 (14)	0.1049 (9)
O12	0.0781 (4)	0.86278 (13)	−0.01724 (12)	0.0748 (6)
C13	−0.0923 (6)	0.8053 (2)	−0.02818 (18)	0.0778 (10)
H13A	−0.2267	0.8353	−0.0279	0.093*
H13B	−0.0942	0.7635	0.0125	0.093*
C14	−0.0582 (8)	0.7632 (2)	−0.1044 (2)	0.0860 (11)
H14	−0.1579	0.7232	−0.1196	0.103*
C15	0.0989 (7)	0.7778 (2)	−0.15084 (19)	0.0906 (12)
H15A	0.2021	0.8173	−0.1378	0.109*
H15B	0.1080	0.7487	−0.1971	0.109*
O16	−0.1951 (4)	0.94477 (13)	0.22389 (13)	0.0729 (7)
C17	−0.1985 (6)	1.0013 (2)	0.28825 (18)	0.0773 (11)
H17A	−0.1929	1.0594	0.2704	0.093*
H17B	−0.0753	0.9912	0.3204	0.093*
C18	−0.3953 (7)	0.9877 (2)	0.3335 (2)	0.0815 (11)
H18	−0.4206	1.0255	0.3733	0.098*
C19	−0.5312 (6)	0.9305 (3)	0.3237 (2)	0.1011 (13)
H19A	−0.5136	0.8910	0.2846	0.121*
H19B	−0.6496	0.9277	0.3555	0.121*
C20	0.7460 (6)	1.1464 (2)	0.0988 (2)	0.0670 (9)
C21	0.9252 (7)	1.1595 (2)	0.0537 (2)	0.0818 (11)
H21	0.9425	1.1292	0.0084	0.098*
C22	1.0767 (7)	1.2170 (3)	0.0757 (3)	0.0980 (13)
H22	1.1961	1.2253	0.0452	0.118*
C23	1.0540 (8)	1.2625 (3)	0.1423 (3)	0.1075 (15)
H23	1.1572	1.3015	0.1568	0.129*
C24	0.8787 (8)	1.2503 (3)	0.1873 (3)	0.1096 (14)
H24	0.8634	1.2806	0.2327	0.131*
C25	0.7248 (6)	1.1932 (2)	0.1657 (2)	0.0887 (11)
H25	0.6052	1.1859	0.1962	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0626 (14)	0.0716 (14)	0.0608 (14)	−0.0033 (13)	0.0010 (14)	0.0035 (11)
C2	0.059 (2)	0.066 (2)	0.067 (2)	0.008 (2)	0.003 (2)	0.0157 (18)
C3	0.071 (2)	0.084 (2)	0.069 (2)	−0.004 (2)	0.016 (2)	0.007 (2)
C4	0.067 (2)	0.079 (2)	0.063 (2)	0.003 (2)	0.006 (2)	0.0007 (19)
C5	0.072 (2)	0.0608 (19)	0.050 (2)	0.007 (2)	−0.003 (2)	0.0017 (16)
C6	0.066 (2)	0.0620 (18)	0.058 (2)	−0.0021 (18)	0.003 (2)	0.0036 (17)
C7	0.062 (2)	0.0673 (19)	0.048 (2)	0.0043 (19)	0.0072 (19)	0.0059 (17)
C8	0.067 (2)	0.0646 (19)	0.0509 (19)	0.0001 (18)	0.001 (2)	0.0015 (16)
C9	0.054 (2)	0.0572 (17)	0.056 (2)	0.0028 (18)	−0.0023 (19)	0.0097 (16)
C10	0.059 (2)	0.0577 (17)	0.051 (2)	0.0056 (19)	0.0027 (18)	0.0042 (15)
O11	0.107 (2)	0.128 (2)	0.0792 (18)	−0.029 (2)	0.0327 (17)	−0.0308 (16)
O12	0.0831 (16)	0.0798 (14)	0.0614 (15)	−0.0099 (15)	0.0049 (14)	−0.0105 (13)
C13	0.086 (3)	0.076 (2)	0.071 (2)	−0.013 (2)	0.002 (2)	−0.0011 (19)
C14	0.110 (3)	0.078 (2)	0.070 (3)	−0.008 (3)	−0.013 (3)	−0.010 (2)
C15	0.118 (3)	0.094 (3)	0.060 (2)	0.011 (3)	−0.004 (3)	−0.007 (2)
O16	0.0753 (17)	0.0844 (14)	0.0591 (14)	−0.0090 (13)	0.0117 (13)	−0.0065 (12)
C17	0.088 (3)	0.088 (2)	0.057 (2)	−0.004 (2)	0.010 (2)	−0.0027 (19)
C18	0.092 (3)	0.092 (3)	0.060 (2)	0.012 (3)	0.000 (3)	0.003 (2)
C19	0.082 (3)	0.125 (3)	0.096 (3)	0.003 (3)	0.010 (3)	−0.010 (3)
C20	0.061 (2)	0.0622 (19)	0.078 (3)	0.002 (2)	−0.004 (2)	0.0161 (19)
C21	0.070 (3)	0.084 (2)	0.092 (3)	0.000 (2)	−0.002 (3)	0.028 (2)
C22	0.072 (3)	0.095 (3)	0.127 (4)	−0.012 (3)	−0.002 (3)	0.044 (3)
C23	0.092 (3)	0.083 (3)	0.147 (5)	−0.021 (3)	−0.015 (4)	0.012 (3)
C24	0.096 (3)	0.100 (3)	0.132 (4)	−0.022 (3)	0.000 (3)	−0.019 (3)
C25	0.077 (3)	0.082 (2)	0.107 (3)	−0.010 (2)	0.005 (3)	−0.010 (2)

Geometric parameters (Å, º) top

O1—C2	1.360 (4)	C14—H14	0.9300
O1—C9	1.378 (3)	C15—H15A	0.9300
C2—C3	1.340 (4)	C15—H15B	0.9300
C2—C20	1.471 (5)	O16—C17	1.434 (3)
C3—C4	1.433 (5)	C17—C18	1.485 (5)
C3—H3	0.9300	C17—H17A	0.9700
C4—O11	1.233 (3)	C17—H17B	0.9700
C4—C10	1.465 (4)	C18—C19	1.256 (4)
C5—O12	1.360 (3)	C18—H18	0.9300
C5—C6	1.373 (4)	C19—H19A	0.9300
C5—C10	1.410 (4)	C19—H19B	0.9300
C6—C7	1.397 (4)	C20—C25	1.387 (4)
C6—H6	0.9300	C20—C21	1.391 (5)
C7—O16	1.364 (4)	C21—C22	1.373 (5)
C7—C8	1.376 (4)	C21—H21	0.9300
C8—C9	1.384 (4)	C22—C23	1.373 (5)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.395 (4)	C23—C24	1.368 (6)
O12—C13	1.419 (4)	C23—H23	0.9300
C13—C14	1.501 (4)	C24—C25	1.377 (5)
C13—H13A	0.9700	C24—H24	0.9300
C13—H13B	0.9700	C25—H25	0.9300
C14—C15	1.299 (5)

C2—O1—C9	119.6 (3)	C15—C14—H14	117.2
C3—C2—O1	121.0 (3)	C13—C14—H14	117.2
C3—C2—C20	126.6 (4)	C14—C15—H15A	120.0
O1—C2—C20	112.4 (3)	C14—C15—H15B	120.0
C2—C3—C4	123.8 (3)	H15A—C15—H15B	120.0
C2—C3—H3	118.1	C7—O16—C17	117.8 (3)
C4—C3—H3	118.1	O16—C17—C18	109.7 (3)
O11—C4—C3	121.7 (3)	O16—C17—H17A	109.7
O11—C4—C10	124.1 (3)	C18—C17—H17A	109.7
C3—C4—C10	114.2 (3)	O16—C17—H17B	109.7
O12—C5—C6	123.5 (3)	C18—C17—H17B	109.7
O12—C5—C10	115.0 (3)	H17A—C17—H17B	108.2
C6—C5—C10	121.5 (3)	C19—C18—C17	126.9 (4)
C5—C6—C7	119.6 (3)	C19—C18—H18	116.5
C5—C6—H6	120.2	C17—C18—H18	116.5
C7—C6—H6	120.2	C18—C19—H19A	120.0
O16—C7—C8	124.5 (3)	C18—C19—H19B	120.0
O16—C7—C6	114.0 (3)	H19A—C19—H19B	120.0
C8—C7—C6	121.5 (3)	C25—C20—C21	118.3 (4)
C7—C8—C9	117.2 (3)	C25—C20—C2	121.2 (3)
C7—C8—H8	121.4	C21—C20—C2	120.5 (3)
C9—C8—H8	121.4	C22—C21—C20	120.3 (4)
O1—C9—C8	113.6 (3)	C22—C21—H21	119.8
O1—C9—C10	122.1 (3)	C20—C21—H21	119.8
C8—C9—C10	124.3 (3)	C21—C22—C23	120.7 (4)
C9—C10—C5	115.9 (3)	C21—C22—H22	119.7
C9—C10—C4	118.9 (3)	C23—C22—H22	119.7
C5—C10—C4	125.2 (3)	C24—C23—C22	119.7 (4)
C5—O12—C13	119.6 (3)	C24—C23—H23	120.2
O12—C13—C14	107.1 (3)	C22—C23—H23	120.2
O12—C13—H13A	110.3	C23—C24—C25	120.2 (4)
C14—C13—H13A	110.3	C23—C24—H24	119.9
O12—C13—H13B	110.3	C25—C24—H24	119.9
C14—C13—H13B	110.3	C24—C25—C20	120.8 (4)
H13A—C13—H13B	108.5	C24—C25—H25	119.6
C15—C14—C13	125.6 (4)	C20—C25—H25	119.6

C9—O1—C2—C3	−1.5 (4)	O11—C4—C10—C9	174.5 (3)
C9—O1—C2—C20	179.6 (2)	C3—C4—C10—C9	−5.1 (4)
O1—C2—C3—C4	−4.0 (5)	O11—C4—C10—C5	−5.6 (5)
C20—C2—C3—C4	174.8 (3)	C3—C4—C10—C5	174.8 (3)
C2—C3—C4—O11	−172.6 (3)	C6—C5—O12—C13	−0.4 (4)
C2—C3—C4—C10	7.1 (5)	C10—C5—O12—C13	−179.7 (3)
O12—C5—C6—C7	−179.3 (3)	C5—O12—C13—C14	−178.8 (3)
C10—C5—C6—C7	−0.1 (5)	O12—C13—C14—C15	−0.3 (5)
C5—C6—C7—O16	178.4 (3)	C8—C7—O16—C17	6.5 (4)
C5—C6—C7—C8	−0.8 (5)	C6—C7—O16—C17	−172.7 (3)
O16—C7—C8—C9	−177.9 (3)	C7—O16—C17—C18	173.6 (3)
C6—C7—C8—C9	1.2 (4)	O16—C17—C18—C19	6.9 (5)
C2—O1—C9—C8	−176.4 (2)	C3—C2—C20—C25	173.0 (3)
C2—O1—C9—C10	3.2 (4)	O1—C2—C20—C25	−8.1 (4)
C7—C8—C9—O1	178.8 (2)	C3—C2—C20—C21	−8.2 (5)
C7—C8—C9—C10	−0.9 (4)	O1—C2—C20—C21	170.7 (3)
O1—C9—C10—C5	−179.5 (2)	C25—C20—C21—C22	0.4 (5)
C8—C9—C10—C5	0.1 (4)	C2—C20—C21—C22	−178.4 (3)
O1—C9—C10—C4	0.3 (4)	C20—C21—C22—C23	−0.1 (5)
C8—C9—C10—C4	179.9 (3)	C21—C22—C23—C24	0.2 (6)
O12—C5—C10—C9	179.7 (3)	C22—C23—C24—C25	−0.6 (7)
C6—C5—C10—C9	0.4 (4)	C23—C24—C25—C20	1.0 (6)
O12—C5—C10—C4	−0.1 (4)	C21—C20—C25—C24	−0.9 (5)
C6—C5—C10—C4	−179.4 (3)	C2—C20—C25—C24	178.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O12	0.93	2.35	2.691 (4)	101
C19—H19A···O16	0.93	2.42	2.749 (5)	101
C25—H25···O1	0.93	2.39	2.714 (4)	101
C17—H17B···O11ⁱ	0.97	2.51	3.229 (4)	131
C14—H14···Cg1ⁱⁱ	0.93	3.22	4.081	154

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₄
M_r	334.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.299 (2), 15.798 (6), 17.429 (6)
V (Å³)	1734.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.32 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.969, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	13979, 3543, 1793
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.098, 1.01
No. of reflections	2055
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.10

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O12	0.93	2.35	2.691 (4)	101.0
C19—H19A···O16	0.93	2.42	2.749 (5)	100.6
C25—H25···O1	0.93	2.39	2.714 (4)	100.5
C17—H17B···O11ⁱ	0.97	2.51	3.229 (4)	130.9
C14—H14···Cg1ⁱⁱ	0.93	3.222	4.081	154.42

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

Acknowledgements

AN thanks Dr S. Kannan and Dr B. S. Krishnamurthy, School of Chemistry, Bharathidasan University, Tiruchirappalli, and Organica Aromatics Pvt Ltd Bangalore, India, for providing laboratory facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brooks, G. T. (1998). Pestic. Sci. 22, 41–50. CrossRef Web of Science Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. (1989). Crystal Engineering: The Design of Organic Solids, pp. 125–167. Amsterdam: Elsevier. Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 11–40. New York: Oxford University Press. Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1202–1204. CrossRef Web of Science Google Scholar
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768. Google Scholar
Liu, C.-B., Chen, Y.-H., Zhou, X.-Y., Ding, L. & Wen, H.-L. (2007). Acta Cryst. E63, o90–o91. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. University of Gottingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437–o1438. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Wang, J.-F., Fang, M.-J., Huang, H.-Q., Li, G.-L., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1517–o1518. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, J.-F., Zhang, Y.-J., Fang, M.-J., Huang, Y.-J., Wei, Z.-B., Zheng, Z.-H., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1244–o1245. Web of Science CSD CrossRef IUCr Journals Google Scholar