4-(Oct­yloxy)phenyl 2-oxo-2H-chromene-3-carboxyl­ate

Palakshamurthy, B.S.; Sreenivasa, S.; Srinivasa, H.T.; Roopashree, K.R.; Devarajegowda, H.C.

doi:10.1107/S1600536813000214

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o212

doi:10.1107/S1600536813000214

Open

access

4-(Octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate

B. S. Palakshamurthy,^a S. Sreenivasa,^b H. T. Srinivasa,^c K. R. Roopashree ^a and H. C. Devarajegowda ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India, and ^cRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 24 December 2012; accepted 3 January 2013; online 9 January 2013)

In the title compound, C₂₄H₂₆O₅, the 2H-chromene ring system is essentially planar, with a maximum deviation of 0.029 (2) Å from the best-fit mean plane incorporating both rings. The dihedral angle between the 2H-chromene ring system and the benzene ring is 21.00 (1)°. In the crystal, pairs of C—H⋯O hydrogen bonds generate an R₂²(8) ring pattern. These contacts are bolstered by weaker bifurcated C—H⋯O hydrogen bonds.

Related literature

For general background to coumarin derivatives and their biological and technological applications, see: Georgieva et al. (2004 ); Creaven et al. (2005 ); Morita et al. (2005 ); Tian et al. (2003 ); Iliopoulos et al. (2010 ); Hejchman et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₆O₅
M_r = 394.45
Monoclinic, P 2₁ /n
a = 14.464 (3) Å
b = 6.7548 (15) Å
c = 21.381 (5) Å
β = 91.663 (8)°
V = 2088.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.29 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.975, T_max = 0.982
22609 measured reflections
3615 independent reflections
1926 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.146
S = 0.94
3615 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.93	2.59	3.513 (4)	174
C9—H9⋯O2ⁱ	0.93	2.51	3.420 (3)	167
C16—H16⋯O2ⁱ	0.93	2.71	3.551 (3)	151
C16—H16⋯O3ⁱ	0.93	2.63	3.338 (3)	133
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000214/sj5291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000214/sj5291Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000214/sj5291Isup3.cml

checkCIF report

Comment top

Coumarin derivatives have been attracted increasing attention due to their extensive biological applications, such as anticancer, anti-inflammatory and anticoagulant agents (Georgieva et al., 2004; Creaven et al., 2005). The coumarin nucleus has been the focus of our recent research concerning the design, synthesis and characterization to investigate their liquid crystal properties together with crystal structure studies (Morita et al., 2005; Tian et al., 2003). Coumarins are interesting class of heterocycles because of their dipolar moment increases by external stimulus such as light, temperature, electric current and chemical reaction (Iliopoulos et al., 2010). The excitation of the coumarin chromophore increases the electron density of its carbonyl groups owing to excited photochemical and photophysical properties such as molecular fluorescent sensors, laser dyes and many industrial applications (Hejchman et al., 2011).

The asymmetric unit of 4-(octyloxy)phenyl 2-oxo-2H-chromene-3 -carboxylate is shown in Fig. 1. The 2H-chromene ring (O1/C1–C9) system is planar, with a maximum deviation of 0.028 (2) Å for atom C8. The dihedral angle between 2H-chromene ring (O1/C1–C9) and benzene ring (C11–C16) is 21.11 (1)°. The crystal structure is characterized by intermolecular C4—H4···O1 and C9—H9···O2 hydrogen bonding generating an R₂ ²(8) ring pattern (Bernstein et al., 1995). Bifurcated C16—H16···O2 and C16—H16···O3 contacts further strengthen the packing, Fig. 2.

Related literature top

For general background to coumarin derivatives and their biological and technological applications, see: Georgieva et al. (2004); Creaven et al. (2005); Morita et al. (2005); Tian et al. (2003); Iliopoulos et al. (2010); Hejchman et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 2-oxo-2H-chromene-3-carboxylic acid (19 mg,1 mmol), 4-(octyloxy)phenol (22.2 mg,1 mmol), N,N -dicyclohexylcarbodiimide (23 mg,1.2 mmol) and a catalytic quantity of N,N-dimethylaminopyrimidine was stirred in 5 ml of dry dichloromethane for 24 h at room temperature. The residue obtained on removal of solvent was chromatographed on silica gel and eluted with chloroform. Removal of solvent from the eluate afforded a colorless solid, which was re-crystallized from absolute ethanol to obtain needle like crystals of the title compound for X-ray diffraction analysis.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Crystal packing for the title compound with hydrogen bonds drawn as dashed lines.

4-(Octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate top

Crystal data top

C₂₄H₂₆O₅	F(000) = 840
M_r = 394.45	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 580 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.464 (3) Å	Cell parameters from 3615 reflections
b = 6.7548 (15) Å	θ = 3.2–25.0°
c = 21.381 (5) Å	µ = 0.09 mm⁻¹
β = 91.663 (8)°	T = 293 K
V = 2088.0 (8) Å³	Needles, colourless
Z = 4	0.29 × 0.25 × 0.21 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3615 independent reflections
Radiation source: fine-focus sealed tube	1926 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ω and ϕ scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −17→16
T_min = 0.975, T_max = 0.982	k = −8→5
22609 measured reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.077P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
3615 reflections	Δρ_max = 0.18 e Å⁻³
264 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (7)

Crystal data top

C₂₄H₂₆O₅	V = 2088.0 (8) Å³
M_r = 394.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.464 (3) Å	µ = 0.09 mm⁻¹
b = 6.7548 (15) Å	T = 293 K
c = 21.381 (5) Å	0.29 × 0.25 × 0.21 mm
β = 91.663 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3615 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1926 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.084
22609 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 0.94	Δρ_max = 0.18 e Å⁻³
3615 reflections	Δρ_min = −0.14 e Å⁻³
264 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.11082 (14)	0.0294 (3)	−0.01675 (8)	0.0705 (6)
O2	0.11756 (15)	−0.1104 (3)	0.07552 (9)	0.0826 (7)
O3	0.06844 (14)	0.1538 (3)	0.17685 (9)	0.0744 (6)
O4	0.14523 (12)	0.4373 (2)	0.16091 (7)	0.0610 (5)
O5	0.14206 (14)	0.7392 (3)	0.40100 (8)	0.0730 (6)
C1	0.1075 (2)	0.1595 (5)	−0.11861 (13)	0.0755 (9)
H1	0.1043	0.0314	−0.1345	0.091*
C2	0.1090 (2)	0.3196 (5)	−0.15818 (14)	0.0827 (9)
H2	0.1062	0.2995	−0.2012	0.099*
C3	0.1146 (2)	0.5101 (5)	−0.13485 (14)	0.0775 (9)
H3	0.1165	0.6174	−0.1620	0.093*
C4	0.11723 (19)	0.5398 (4)	−0.07203 (13)	0.0682 (8)
H4	0.1203	0.6682	−0.0564	0.082*
C5	0.11538 (17)	0.3810 (4)	−0.03071 (11)	0.0509 (6)
C6	0.11088 (18)	0.1917 (4)	−0.05564 (12)	0.0557 (7)
C7	0.11337 (19)	0.0428 (4)	0.04771 (12)	0.0603 (7)
C8	0.11338 (17)	0.2423 (3)	0.07410 (11)	0.0497 (6)
C9	0.11632 (16)	0.3995 (4)	0.03580 (11)	0.0524 (7)
H9	0.1191	0.5255	0.0533	0.063*
C10	0.10603 (18)	0.2654 (4)	0.14224 (12)	0.0531 (7)
C11	0.13845 (18)	0.5046 (4)	0.22323 (11)	0.0535 (7)
C12	0.16625 (19)	0.3932 (4)	0.27383 (12)	0.0639 (8)
H12	0.1845	0.2623	0.2686	0.077*
C13	0.16691 (19)	0.4769 (4)	0.33248 (12)	0.0650 (8)
H13	0.1863	0.4028	0.3671	0.078*
C14	0.13875 (19)	0.6712 (4)	0.34023 (11)	0.0567 (7)
C15	0.11116 (19)	0.7799 (4)	0.28884 (11)	0.0619 (7)
H15	0.0923	0.9104	0.2938	0.074*
C16	0.11120 (19)	0.6972 (4)	0.22990 (11)	0.0591 (7)
H16	0.0929	0.7715	0.1951	0.071*
C17	0.1323 (2)	0.9462 (4)	0.41084 (12)	0.0645 (7)
H17A	0.0739	0.9916	0.3926	0.077*
H17B	0.1819	1.0168	0.3909	0.077*
C18	0.1356 (2)	0.9869 (4)	0.47999 (11)	0.0675 (8)
H18A	0.1914	0.9287	0.4984	0.081*
H18B	0.0831	0.9239	0.4989	0.081*
C19	0.1343 (2)	1.2047 (4)	0.49476 (12)	0.0707 (8)
H19A	0.0812	1.2634	0.4731	0.085*
H19B	0.1893	1.2646	0.4780	0.085*
C20	0.1304 (2)	1.2574 (4)	0.56327 (12)	0.0723 (8)
H20A	0.0761	1.1960	0.5806	0.087*
H20B	0.1843	1.2027	0.5850	0.087*
C21	0.1269 (2)	1.4752 (5)	0.57543 (13)	0.0831 (9)
H21A	0.0717	1.5278	0.5546	0.100*
H21B	0.1797	1.5360	0.5562	0.100*
C22	0.1265 (2)	1.5383 (5)	0.64278 (13)	0.0839 (9)
H22A	0.1818	1.4883	0.6641	0.101*
H22B	0.0734	1.4801	0.6625	0.101*
C23	0.1229 (3)	1.7629 (5)	0.65022 (15)	0.1031 (12)
H23A	0.1746	1.8199	0.6287	0.124*
H23B	0.0666	1.8108	0.6295	0.124*
C24	0.1255 (3)	1.8364 (6)	0.71544 (16)	0.1332 (16)
H24A	0.0720	1.7894	0.7365	0.200*
H24B	0.1256	1.9785	0.7153	0.200*
H24C	0.1804	1.7889	0.7368	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1120 (16)	0.0356 (11)	0.0641 (12)	−0.0062 (10)	0.0039 (10)	−0.0070 (9)
O2	0.1353 (19)	0.0309 (12)	0.0816 (14)	−0.0007 (11)	0.0057 (12)	0.0064 (10)
O3	0.1055 (16)	0.0459 (12)	0.0723 (12)	−0.0202 (11)	0.0096 (11)	0.0020 (10)
O4	0.0867 (14)	0.0398 (11)	0.0564 (11)	−0.0166 (9)	0.0003 (9)	−0.0004 (9)
O5	0.1129 (17)	0.0487 (13)	0.0570 (12)	0.0036 (10)	−0.0023 (10)	−0.0017 (9)
C1	0.103 (2)	0.059 (2)	0.0653 (19)	−0.0103 (16)	0.0005 (16)	−0.0075 (16)
C2	0.098 (3)	0.090 (3)	0.0596 (18)	−0.0053 (19)	−0.0046 (16)	0.0027 (19)
C3	0.097 (3)	0.066 (2)	0.069 (2)	0.0052 (17)	0.0010 (16)	0.0184 (17)
C4	0.082 (2)	0.0507 (18)	0.0718 (19)	0.0039 (15)	0.0006 (15)	0.0067 (16)
C5	0.0562 (17)	0.0401 (16)	0.0562 (15)	0.0004 (12)	−0.0026 (12)	0.0034 (13)
C6	0.0659 (19)	0.0445 (17)	0.0566 (16)	−0.0040 (13)	−0.0021 (13)	−0.0030 (14)
C7	0.075 (2)	0.0386 (17)	0.0672 (18)	−0.0039 (13)	0.0036 (14)	−0.0036 (15)
C8	0.0573 (17)	0.0307 (14)	0.0608 (16)	−0.0013 (11)	−0.0018 (12)	0.0018 (13)
C9	0.0623 (18)	0.0326 (15)	0.0622 (16)	0.0006 (12)	−0.0020 (12)	−0.0042 (12)
C10	0.0590 (17)	0.0361 (16)	0.0639 (17)	−0.0016 (13)	−0.0025 (13)	0.0025 (14)
C11	0.0697 (19)	0.0365 (15)	0.0542 (15)	−0.0078 (12)	0.0018 (12)	0.0008 (13)
C12	0.087 (2)	0.0373 (15)	0.0670 (18)	0.0048 (14)	−0.0062 (15)	0.0005 (14)
C13	0.092 (2)	0.0435 (17)	0.0588 (17)	0.0071 (14)	−0.0091 (14)	0.0103 (14)
C14	0.0749 (19)	0.0434 (17)	0.0515 (16)	−0.0048 (13)	−0.0026 (13)	0.0046 (13)
C15	0.088 (2)	0.0377 (15)	0.0599 (17)	0.0002 (14)	−0.0029 (14)	0.0023 (13)
C16	0.081 (2)	0.0369 (16)	0.0588 (17)	−0.0038 (13)	−0.0064 (14)	0.0094 (13)
C17	0.077 (2)	0.0548 (19)	0.0615 (17)	0.0054 (14)	0.0026 (13)	−0.0055 (14)
C18	0.069 (2)	0.070 (2)	0.0638 (17)	0.0044 (15)	0.0027 (13)	−0.0025 (15)
C19	0.090 (2)	0.0596 (19)	0.0627 (17)	−0.0049 (16)	0.0010 (15)	−0.0041 (15)
C20	0.086 (2)	0.060 (2)	0.0706 (19)	−0.0015 (15)	0.0053 (15)	−0.0064 (15)
C21	0.106 (3)	0.067 (2)	0.076 (2)	0.0033 (18)	−0.0015 (17)	−0.0039 (17)
C22	0.102 (3)	0.074 (2)	0.077 (2)	0.0031 (18)	0.0093 (17)	−0.0084 (18)
C23	0.152 (3)	0.077 (3)	0.080 (2)	0.015 (2)	0.004 (2)	−0.0115 (19)
C24	0.204 (5)	0.110 (3)	0.088 (3)	0.014 (3)	0.028 (3)	−0.014 (2)

Geometric parameters (Å, º) top

O1—C6	1.376 (3)	C14—C15	1.371 (3)
O1—C7	1.381 (3)	C15—C16	1.379 (3)
O2—C7	1.194 (3)	C15—H15	0.9300
O3—C10	1.198 (3)	C16—H16	0.9300
O4—C10	1.347 (3)	C17—C18	1.503 (3)
O4—C11	1.414 (3)	C17—H17A	0.9700
O5—C14	1.378 (3)	C17—H17B	0.9700
O5—C17	1.422 (3)	C18—C19	1.505 (4)
C1—C6	1.363 (3)	C18—H18A	0.9700
C1—C2	1.374 (4)	C18—H18B	0.9700
C1—H1	0.9300	C19—C20	1.510 (3)
C2—C3	1.381 (4)	C19—H19A	0.9700
C2—H2	0.9300	C19—H19B	0.9700
C3—C4	1.357 (3)	C20—C21	1.496 (4)
C3—H3	0.9300	C20—H20A	0.9700
C4—C5	1.390 (3)	C20—H20B	0.9700
C4—H4	0.9300	C21—C22	1.502 (4)
C5—C6	1.386 (3)	C21—H21A	0.9700
C5—C9	1.427 (3)	C21—H21B	0.9700
C7—C8	1.461 (3)	C22—C23	1.527 (4)
C8—C9	1.342 (3)	C22—H22A	0.9700
C8—C10	1.472 (3)	C22—H22B	0.9700
C9—H9	0.9300	C23—C24	1.479 (4)
C11—C16	1.368 (4)	C23—H23A	0.9700
C11—C12	1.369 (3)	C23—H23B	0.9700
C12—C13	1.375 (3)	C24—H24A	0.9600
C12—H12	0.9300	C24—H24B	0.9600
C13—C14	1.386 (4)	C24—H24C	0.9600
C13—H13	0.9300

C6—O1—C7	123.4 (2)	C15—C16—H16	120.4
C10—O4—C11	121.06 (19)	O5—C17—C18	109.0 (2)
C14—O5—C17	117.82 (19)	O5—C17—H17A	109.9
C6—C1—C2	118.8 (3)	C18—C17—H17A	109.9
C6—C1—H1	120.6	O5—C17—H17B	109.9
C2—C1—H1	120.6	C18—C17—H17B	109.9
C1—C2—C3	120.8 (3)	H17A—C17—H17B	108.3
C1—C2—H2	119.6	C17—C18—C19	112.6 (2)
C3—C2—H2	119.6	C17—C18—H18A	109.1
C4—C3—C2	119.6 (3)	C19—C18—H18A	109.1
C4—C3—H3	120.2	C17—C18—H18B	109.1
C2—C3—H3	120.2	C19—C18—H18B	109.1
C3—C4—C5	120.9 (3)	H18A—C18—H18B	107.8
C3—C4—H4	119.5	C18—C19—C20	115.8 (2)
C5—C4—H4	119.5	C18—C19—H19A	108.3
C6—C5—C4	117.9 (2)	C20—C19—H19A	108.3
C6—C5—C9	117.6 (2)	C18—C19—H19B	108.3
C4—C5—C9	124.5 (2)	C20—C19—H19B	108.3
C1—C6—O1	118.0 (2)	H19A—C19—H19B	107.4
C1—C6—C5	121.8 (2)	C21—C20—C19	113.8 (2)
O1—C6—C5	120.2 (2)	C21—C20—H20A	108.8
O2—C7—O1	116.1 (2)	C19—C20—H20A	108.8
O2—C7—C8	127.4 (2)	C21—C20—H20B	108.8
O1—C7—C8	116.5 (2)	C19—C20—H20B	108.8
C9—C8—C7	119.6 (2)	H20A—C20—H20B	107.7
C9—C8—C10	121.6 (2)	C20—C21—C22	116.5 (3)
C7—C8—C10	118.7 (2)	C20—C21—H21A	108.2
C8—C9—C5	122.6 (2)	C22—C21—H21A	108.2
C8—C9—H9	118.7	C20—C21—H21B	108.2
C5—C9—H9	118.7	C22—C21—H21B	108.2
O3—C10—O4	123.6 (2)	H21A—C21—H21B	107.3
O3—C10—C8	126.3 (2)	C21—C22—C23	112.5 (3)
O4—C10—C8	110.0 (2)	C21—C22—H22A	109.1
C16—C11—C12	121.3 (2)	C23—C22—H22A	109.1
C16—C11—O4	115.6 (2)	C21—C22—H22B	109.1
C12—C11—O4	122.8 (2)	C23—C22—H22B	109.1
C11—C12—C13	119.3 (2)	H22A—C22—H22B	107.8
C11—C12—H12	120.4	C24—C23—C22	115.6 (3)
C13—C12—H12	120.4	C24—C23—H23A	108.4
C12—C13—C14	120.3 (2)	C22—C23—H23A	108.4
C12—C13—H13	119.9	C24—C23—H23B	108.4
C14—C13—H13	119.9	C22—C23—H23B	108.4
C15—C14—O5	125.3 (2)	H23A—C23—H23B	107.4
C15—C14—C13	119.4 (2)	C23—C24—H24A	109.5
O5—C14—C13	115.2 (2)	C23—C24—H24B	109.5
C14—C15—C16	120.5 (3)	H24A—C24—H24B	109.5
C14—C15—H15	119.7	C23—C24—H24C	109.5
C16—C15—H15	119.7	H24A—C24—H24C	109.5
C11—C16—C15	119.2 (2)	H24B—C24—H24C	109.5
C11—C16—H16	120.4

C6—C1—C2—C3	0.6 (5)	C9—C8—C10—O3	148.8 (3)
C1—C2—C3—C4	−1.0 (5)	C7—C8—C10—O3	−28.5 (4)
C2—C3—C4—C5	0.7 (4)	C9—C8—C10—O4	−28.8 (3)
C3—C4—C5—C6	0.1 (4)	C7—C8—C10—O4	153.9 (2)
C3—C4—C5—C9	−178.9 (2)	C10—O4—C11—C16	−131.1 (3)
C2—C1—C6—O1	−179.0 (3)	C10—O4—C11—C12	55.5 (3)
C2—C1—C6—C5	0.2 (4)	C16—C11—C12—C13	−0.1 (4)
C7—O1—C6—C1	−179.5 (2)	O4—C11—C12—C13	172.9 (2)
C7—O1—C6—C5	1.2 (4)	C11—C12—C13—C14	0.7 (4)
C4—C5—C6—C1	−0.6 (4)	C17—O5—C14—C15	−11.9 (4)
C9—C5—C6—C1	178.5 (2)	C17—O5—C14—C13	167.5 (2)
C4—C5—C6—O1	178.7 (2)	C12—C13—C14—C15	−0.7 (4)
C9—C5—C6—O1	−2.3 (4)	C12—C13—C14—O5	179.8 (2)
C6—O1—C7—O2	−176.5 (2)	O5—C14—C15—C16	179.5 (2)
C6—O1—C7—C8	1.8 (4)	C13—C14—C15—C16	0.1 (4)
O2—C7—C8—C9	174.3 (3)	C12—C11—C16—C15	−0.5 (4)
O1—C7—C8—C9	−3.8 (4)	O4—C11—C16—C15	−174.0 (2)
O2—C7—C8—C10	−8.4 (4)	C14—C15—C16—C11	0.5 (4)
O1—C7—C8—C10	173.6 (2)	C14—O5—C17—C18	178.6 (2)
C7—C8—C9—C5	2.8 (4)	O5—C17—C18—C19	174.9 (2)
C10—C8—C9—C5	−174.5 (2)	C17—C18—C19—C20	175.7 (2)
C6—C5—C9—C8	0.3 (4)	C18—C19—C20—C21	−178.6 (3)
C4—C5—C9—C8	179.2 (3)	C19—C20—C21—C22	−177.7 (3)
C11—O4—C10—O3	−4.6 (4)	C20—C21—C22—C23	180.0 (3)
C11—O4—C10—C8	173.1 (2)	C21—C22—C23—C24	−178.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.59	3.513 (4)	174
C9—H9···O2ⁱ	0.93	2.51	3.420 (3)	167
C16—H16···O2ⁱⁱ	0.93	2.71	3.551 (3)	151
C16—H16···O3ⁱⁱ	0.93	2.63	3.338 (3)	133

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆O₅
M_r	394.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.464 (3), 6.7548 (15), 21.381 (5)
β (°)	91.663 (8)
V (Å³)	2088.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.29 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.975, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	22609, 3615, 1926
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.146, 0.94
No. of reflections	3615
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.5900	3.513 (4)	174.00
C9—H9···O2ⁱ	0.93	2.5100	3.420 (3)	167.00
C16—H16···O2ⁱⁱ	0.93	2.71	3.551 (3)	150.67
C16—H16···O3ⁱⁱ	0.93	2.63	3.338 (3)	132.93

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

Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, and P. A. Suchetan, Department of Studies and Research in Chemistry, U·C.S. Tumkur University, Tumkur, for their help and suggestions.

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
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Creaven, B. S., Egan, D. A., Kavanagh, K., McCann, M., Mahon, M., Noble, A., Thati, B. & Walsh, M. (2005). Polyhedron, 24, 949–957. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Georgieva, I., Mihaylov, T., Bauer, G. & Trendafilova, N. (2004). Chem. Phys. 300, 119–131. Web of Science CrossRef CAS Google Scholar
Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392–2402. Web of Science CrossRef CAS Google Scholar
Iliopoulos, K., Krupka, O., Gindre, D. & Salle, M. (2010). J. Am. Chem. Soc. 132, 14343–14345. Web of Science CrossRef CAS PubMed Google Scholar
Morita, Y., Tasaka, T., Yamaguchi, R., Okamoto, H. & Takenaka, S. (2005). Mol. Cryst. Liq. Cryst. 439, 209–220. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, Y., Akiyamab, E. & Nagase, Y. (2003). J. Mater. Chem. 13, 1253–1258. Web of Science CrossRef CAS Google Scholar