Crystal structure of 4-meth­oxy­phenyl 2-oxo-2H-chromene-3-carboxyl­ate

Devarajegowda, H.C.; Suchetan, P.A.; Sreenivasa, S.; Srinivasa, H.T.; Palakshamurthy, B.S.

doi:10.1107/S2056989015006970

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o374-o375

doi:10.1107/S2056989015006970

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Crystal structure of 4-methoxyphenyl 2-oxo-2H-chromene-3-carboxylate

H.C. Devarajegowda,^a P. A. Suchetan,^b S. Sreenivasa,^b H. T. Srinivasa ^c and B. S. Palakshamurthy ^a ^*

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 April 2015; accepted 7 April 2015; online 7 May 2015)

In the title compound, C₁₇H₁₂O₅, the dihedral angle between the planes of the coumarin ring system (r.m.s. deviation = 0.015 Å) and the benzene ring is 48.04 (10)°. The central CO₂ group subtends a dihedral angle of 27.15 (11)° with the coumarin ring system and 74.86 (13)° with the benzene ring. In the crystal, molecules are linked by C—H⋯O interactions, which generate a three-dimensional network. Very weak C—H⋯π interactions are also observed.

Keywords: crystal structure; 2-oxo-2H-chromene; C—H⋯π interactions; C—H⋯O interactions.

CCDC reference: 1058259

1. Related literature

For details of the biological activies of 2-oxo-2H-chromene derivatives, see: Kawase et al. (2001 ); Traven (2004 ); Lacy & O'Kennedy (2004 ); Chimenti et al. (2009 ). For related structures, see: Sreenivasa et al. (2013 ); Devarajegowda et al., (2013 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₂O₅
M_r = 296.27
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2648 (18) Å
b = 10.435 (3) Å
c = 20.621 (7) Å
V = 1348.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.18 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.977, T_max = 0.981
10472 measured reflections
2385 independent reflections
2150 reflections with I > 2σ(I)
R_int = 0.050

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.085
S = 1.09
1411 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C6/C7/C8/C9/O1 and C1/C2/C3/C4/C5/C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯O5ⁱ	0.96	2.50	3.228 (3)	132
C12—H12⋯O2ⁱⁱ	0.93	2.48	3.353 (3)	156
C15—H15⋯O2ⁱⁱⁱ	0.93	2.50	3.207 (3)	133
C3—H3⋯O3^iv	0.93	2.47	3.272 (4)	145
C5—H5⋯Cg1^v	0.93	2.82	3.303 (3)	114
C17—H17C⋯Cg2^vi	0.93	2.96	3.709 (4)	136
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x-1, y, z; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (v) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z-1]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Supporting information

CCDC reference: 1058259

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015006970/hb7399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015006970/hb7399Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015006970/hb7399Isup3.cml

checkCIF report

Chemical context top

The 2-oxo-2H-chromene is a useful starting material for the construction of heterocyclic compounds with a broad spectrum of biological activities. Especially the 3-substituted derivatives exhibits pharmacological effects such as analgesic, anti-arthritis, anti-inflammatory, anti-pyretic, anti-viral, anti-cancer and anticoagulant properties (Chimenti et al., 2009; Traven et al., 2004; Lacy et al., 2004). Moreover, these derivatives are well known for their anti-microbial activity toward different microorganisms, they show anti-microbial activity with reference to anti-H. pylori activity.(Kawase et al., 2001).

2-oxo-2H-chromenes (coumarins) have been also used in the field of medicine, cosmetics and fluorescent dyes. They are efficient fluorophores characterized by good emission quantum yields and are used as materials for lasers in organic light emitting devices, non-linear optical chromophores and fluorescent labels. Keeping these facts in mind and in continuation of our work on 2-oxo-2H-chromene derivatives (Sreenivasa et al., 2013; Palakshamurthy, Sreenivasa et al., 2013; Palakshamurthy, Devarajegowda et al., 2013; Devarajegowda, et al.,2013), herein we report the synthesis and crystal structure of 4-Methoxyphenyl 2-oxo-2H-chromene-3-carboxylate (I).

Structural commentary top

In the title molecule (I), C₁₇H₁₂O₅, the coumarin ring is almost planar, the rms deviation (considering non Hydrogen atom) being 0.012 (1)Å. The dihedral angle between the coumarin ring and the phenyl ring in (I) is 48.04 (10)^o. Compared to this, the dihedral angle is 21.11 (1)° in 4-(octyloxy)phenyl 2-oxo-2H-chromene-3 -carboxylate (II) (Palakshamurthy, Devarajegowda et al., 2013), 62.97 (2)^o in 4-(decyloxy)phenyl 7-(trifluoromethyl)-2-oxo-2H-chromene-3-carboxylate (III) (Palakshamurthy, Sreenivasa et al., 2013b), 22.95 (11)^o in 4'-Cyanobiphenyl-4-yl 7-diethylamino- 2-oxo-2H-chromene-3-carboxylate (IV) (Sreenivasa et al., 2013) and 54.46 (17)^o in 4-[4-(Heptyloxy)benzoyloxy] phenyl 2-oxo-7- trifluoromethyl-2H-chromene-3- carboxylate (V) (Devarajegowda, et al., 2013). Further, in (I), the dihedral angle between the central ester chain [C8—C10(O3)—O4] and the phenyl ring and the coumarin ring are 74.86 (10)^o and 27.16 (8)^o respectively. The methoxy group is slightly out of plane from the attached benzene ring, the C17—O5—C14—C13 torsion being 10.3 (3)^o.

Supramolecular features top

In the crystal structure, the molecules are linked into zig-zag C9 chains along c axis via C3—H3···O3 intermolecular interactions. Further, C12—H12···O2 interactions between the molecules in the neighbouring chains leads to C8 chains along a axis, and thus forming sheets in the ac plane. These sheets are interconnected via an intermolecular C15—H15···O2 interactions which form helical C7 chains running along b axis, and hence a three dimensional architecture is displayed. An additional C17—H17B···O5 interactions between the molecules in the neighbouring C7 helical chains leading to the formation of C3 chains along a axis results in sheets along ab plane. Thus, a grid like three dimensional structure is observed. Packing of the molecules displaying the columns formed along a axis is shown in Figure 2.

The packing also features C5—H5···Cg1 and C17—H17C···Cg2 interactions (where Cg1 and the Cg2 are the centroids of the rings C1/C6/C7/C8/C9/O1 and C1/C2/C3/C4/C5/C6 respectively), as shown in Figure 3.

Synthesis and crystallization top

A solution of dicyclohexylcarbodiimide (DCC) dissolved in dried CH₂Cl₂ was added to a solution containing coumarin 3-carboxylic acid (1.0 mmol) and 4-methoxyphenol (1.0 mmol) and a catalytic amount of N—N-Dimethylaminopyrimidine (DMAP) in anhydrous dichloromethane (CH₂Cl₂), under stirring, After 24 hrs of stirring, dicyclohexylurea was filtered off and the solution was concentrated. The solid residue was purified by column chromatography on silica gel (60–120) using chloroform (CHCl₃) as an eluent. Colourless prisms of the title compound were grown by slow evaporation of an ethanol solution at room temperature.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.99 Å. All H-atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

Related literature top

For details of the biological activies of 2-oxo-2H-chromene derivatives, see: Kawase et al. (2001); Traven (2004); Lacy et al. (2004); Chimenti et al. (2009). For realted structures, see: Sreenivasa et al. (2013); Devarajegowda et al., (2013).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The packing of (I) showing grid like structure when viewed along a axis.
	Fig. 3. The packing of (I) showing C—H···π interactions when viewed along a axis.
	Fig. 4. The formation of the title compound.

4-Methoxyphenyl 2-oxo-2H-chromene-3-carboxylate top

Crystal data top

C₁₇H₁₂O₅	D_x = 1.460 Mg m⁻³
M_r = 296.27	Melting point: 435 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.2648 (18) Å	Cell parameters from 2385 reflections
b = 10.435 (3) Å	θ = 2.0–25.0°
c = 20.621 (7) Å	µ = 0.11 mm⁻¹
V = 1348.0 (7) Å³	T = 296 K
Z = 4	Prism, colourless
F(000) = 616	0.22 × 0.20 × 0.18 mm
prism

Data collection top

Bruker APEXII CCD diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	2150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 2.01 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
phi and ω scans	h = −7→5
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
T_min = 0.977, T_max = 0.981	l = −24→23
10472 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0342P)² + 0.2933P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1411 reflections	Δρ_max = 0.16 e Å⁻³
201 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.010 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₇H₁₂O₅	V = 1348.0 (7) Å³
M_r = 296.27	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.2648 (18) Å	µ = 0.11 mm⁻¹
b = 10.435 (3) Å	T = 296 K
c = 20.621 (7) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	2385 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2150 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.050
10472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.09	Δρ_max = 0.16 e Å⁻³
1411 reflections	Δρ_min = −0.16 e Å⁻³
201 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O5	0.2218 (3)	0.80557 (17)	0.42819 (9)	0.0181 (5)
O4	0.5756 (3)	0.70623 (17)	0.18810 (9)	0.0213 (5)
O1	1.0215 (3)	0.54316 (17)	0.02385 (9)	0.0172 (5)
O2	1.1382 (3)	0.53880 (19)	0.12431 (9)	0.0221 (5)
O3	0.8203 (3)	0.56290 (18)	0.22324 (9)	0.0216 (5)
C17	0.0344 (5)	0.7406 (3)	0.44957 (15)	0.0235 (7)
H17A	−0.0827	0.7619	0.4215	0.035*
H17B	0.0014	0.7664	0.4931	0.035*
H17C	0.0584	0.6497	0.4484	0.035*
C14	0.3033 (5)	0.7725 (2)	0.36853 (13)	0.0146 (6)
C13	0.1987 (5)	0.6954 (2)	0.32378 (13)	0.0185 (6)
H13	0.0656	0.6606	0.3333	0.022*
C12	0.2960 (5)	0.6709 (2)	0.26457 (14)	0.0195 (7)
H12	0.2284	0.6191	0.2341	0.023*
C11	0.4914 (5)	0.7230 (2)	0.25097 (13)	0.0189 (6)
C10	0.7332 (4)	0.6180 (2)	0.17961 (14)	0.0164 (6)
C8	0.7751 (4)	0.6021 (2)	0.10923 (13)	0.0143 (6)
C9	0.9873 (5)	0.5583 (2)	0.08977 (13)	0.0153 (6)
C1	0.8638 (5)	0.5612 (2)	−0.02156 (13)	0.0155 (6)
C2	0.9148 (5)	0.5377 (2)	−0.08562 (14)	0.0204 (7)
H2	1.0497	0.5080	−0.0969	0.024*
C3	0.7610 (5)	0.5592 (3)	−0.13272 (14)	0.0223 (7)
H3	0.7935	0.5448	−0.1761	0.027*
C7	0.6224 (5)	0.6229 (2)	0.06469 (13)	0.0148 (6)
H7	0.4887	0.6511	0.0781	0.018*
C6	0.6609 (4)	0.6025 (2)	−0.00282 (13)	0.0153 (6)
C5	0.5082 (5)	0.6226 (2)	−0.05175 (13)	0.0181 (6)
H5	0.3717	0.6500	−0.0407	0.022*
C4	0.5591 (5)	0.6021 (3)	−0.11558 (14)	0.0204 (7)
H4	0.4575	0.6169	−0.1476	0.024*
C15	0.5015 (5)	0.8245 (2)	0.35439 (13)	0.0173 (6)
H15	0.5705	0.8756	0.3849	0.021*
C16	0.5972 (5)	0.8008 (3)	0.29511 (14)	0.0187 (7)
H16	0.7294	0.8361	0.2851	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0178 (11)	0.0206 (9)	0.0160 (11)	−0.0012 (9)	0.0043 (8)	−0.0010 (8)
O4	0.0249 (12)	0.0249 (10)	0.0140 (11)	0.0105 (9)	0.0029 (8)	0.0000 (8)
O1	0.0158 (11)	0.0205 (9)	0.0154 (11)	0.0007 (9)	0.0018 (8)	−0.0017 (8)
O2	0.0175 (12)	0.0299 (11)	0.0189 (11)	0.0057 (9)	−0.0032 (9)	−0.0045 (8)
O3	0.0218 (12)	0.0276 (10)	0.0153 (11)	0.0042 (10)	−0.0001 (9)	0.0035 (8)
C17	0.0247 (19)	0.0205 (14)	0.0252 (17)	−0.0036 (13)	0.0078 (14)	0.0008 (12)
C14	0.0177 (16)	0.0133 (12)	0.0128 (15)	0.0039 (12)	0.0004 (12)	0.0022 (10)
C13	0.0173 (16)	0.0183 (13)	0.0198 (16)	0.0002 (13)	−0.0019 (13)	0.0006 (12)
C12	0.0230 (18)	0.0187 (14)	0.0169 (16)	0.0033 (13)	−0.0034 (13)	−0.0039 (11)
C11	0.0223 (17)	0.0198 (14)	0.0146 (15)	0.0070 (13)	0.0012 (12)	0.0007 (12)
C10	0.0139 (16)	0.0148 (13)	0.0204 (17)	−0.0021 (12)	0.0000 (13)	0.0012 (12)
C8	0.0154 (16)	0.0114 (12)	0.0163 (15)	−0.0017 (11)	0.0004 (12)	−0.0005 (11)
C9	0.0195 (17)	0.0125 (12)	0.0138 (15)	−0.0008 (12)	0.0019 (13)	−0.0013 (10)
C1	0.0186 (17)	0.0118 (12)	0.0162 (15)	−0.0028 (12)	−0.0013 (12)	0.0016 (11)
C2	0.0233 (17)	0.0151 (13)	0.0228 (17)	−0.0018 (12)	0.0056 (13)	−0.0018 (12)
C3	0.034 (2)	0.0186 (13)	0.0145 (16)	−0.0064 (13)	0.0031 (14)	−0.0009 (12)
C7	0.0135 (16)	0.0108 (12)	0.0202 (17)	−0.0005 (11)	0.0021 (12)	−0.0003 (11)
C6	0.0183 (17)	0.0097 (11)	0.0178 (16)	−0.0030 (12)	0.0017 (13)	0.0010 (11)
C5	0.0211 (17)	0.0127 (13)	0.0206 (16)	0.0006 (12)	−0.0020 (14)	0.0011 (11)
C4	0.0298 (19)	0.0143 (13)	0.0171 (16)	−0.0027 (13)	−0.0056 (13)	0.0017 (11)
C15	0.0188 (16)	0.0143 (12)	0.0189 (15)	−0.0001 (12)	−0.0030 (13)	−0.0019 (11)
C16	0.0125 (15)	0.0220 (14)	0.0216 (16)	0.0013 (12)	0.0020 (12)	0.0013 (12)

Geometric parameters (Å, º) top

O5—C14	1.376 (3)	C10—C8	1.484 (4)
O5—C17	1.426 (3)	C8—C7	1.344 (4)
O4—C10	1.361 (3)	C8—C9	1.462 (4)
O4—C11	1.411 (3)	C1—C2	1.381 (4)
O1—C1	1.374 (3)	C1—C6	1.397 (4)
O1—C9	1.385 (3)	C2—C3	1.386 (4)
O2—C9	1.201 (3)	C2—H2	0.9300
O3—C10	1.199 (3)	C3—C4	1.388 (4)
C17—H17A	0.9600	C3—H3	0.9300
C17—H17B	0.9600	C7—C6	1.429 (4)
C17—H17C	0.9600	C7—H7	0.9300
C14—C15	1.386 (4)	C6—C5	1.406 (4)
C14—C13	1.389 (4)	C5—C4	1.371 (4)
C13—C12	1.388 (4)	C5—H5	0.9300
C13—H13	0.9300	C4—H4	0.9300
C12—C11	1.368 (4)	C15—C16	1.384 (4)
C12—H12	0.9300	C15—H15	0.9300
C11—C16	1.388 (4)	C16—H16	0.9300

C14—O5—C17	117.6 (2)	O1—C9—C8	116.5 (2)
C10—O4—C11	118.2 (2)	O1—C1—C2	117.5 (3)
C1—O1—C9	122.8 (2)	O1—C1—C6	120.5 (2)
O5—C17—H17A	109.5	C2—C1—C6	122.0 (3)
O5—C17—H17B	109.5	C1—C2—C3	118.7 (3)
H17A—C17—H17B	109.5	C1—C2—H2	120.6
O5—C17—H17C	109.5	C3—C2—H2	120.6
H17A—C17—H17C	109.5	C2—C3—C4	120.5 (3)
H17B—C17—H17C	109.5	C2—C3—H3	119.8
O5—C14—C15	115.0 (2)	C4—C3—H3	119.8
O5—C14—C13	124.4 (3)	C8—C7—C6	121.4 (3)
C15—C14—C13	120.7 (3)	C8—C7—H7	119.3
C12—C13—C14	118.9 (3)	C6—C7—H7	119.3
C12—C13—H13	120.5	C1—C6—C5	117.8 (3)
C14—C13—H13	120.5	C1—C6—C7	118.0 (3)
C11—C12—C13	120.0 (3)	C5—C6—C7	124.2 (3)
C11—C12—H12	120.0	C4—C5—C6	120.5 (3)
C13—C12—H12	120.0	C4—C5—H5	119.8
C12—C11—C16	121.7 (3)	C6—C5—H5	119.8
C12—C11—O4	118.3 (3)	C5—C4—C3	120.5 (3)
C16—C11—O4	119.8 (3)	C5—C4—H4	119.8
O3—C10—O4	123.9 (3)	C3—C4—H4	119.8
O3—C10—C8	126.8 (3)	C16—C15—C14	120.2 (3)
O4—C10—C8	109.2 (2)	C16—C15—H15	119.9
C7—C8—C9	120.7 (3)	C14—C15—H15	119.9
C7—C8—C10	121.6 (3)	C15—C16—C11	118.5 (3)
C9—C8—C10	117.7 (2)	C15—C16—H16	120.7
O2—C9—O1	116.2 (3)	C11—C16—H16	120.7
O2—C9—C8	127.3 (3)

C17—O5—C14—C15	−170.9 (2)	C9—O1—C1—C6	3.2 (3)
C17—O5—C14—C13	10.3 (4)	O1—C1—C2—C3	−177.9 (2)
O5—C14—C13—C12	178.8 (2)	C6—C1—C2—C3	1.8 (4)
C15—C14—C13—C12	0.1 (4)	C1—C2—C3—C4	−0.8 (4)
C14—C13—C12—C11	−0.3 (4)	C9—C8—C7—C6	0.3 (4)
C13—C12—C11—C16	0.0 (4)	C10—C8—C7—C6	−177.4 (2)
C13—C12—C11—O4	−174.0 (2)	O1—C1—C6—C5	178.3 (2)
C10—O4—C11—C12	−103.6 (3)	C2—C1—C6—C5	−1.4 (4)
C10—O4—C11—C16	82.4 (3)	O1—C1—C6—C7	−1.1 (3)
C11—O4—C10—O3	−8.0 (4)	C2—C1—C6—C7	179.3 (2)
C11—O4—C10—C8	171.6 (2)	C8—C7—C6—C1	−0.6 (4)
O3—C10—C8—C7	151.7 (3)	C8—C7—C6—C5	−179.9 (2)
O4—C10—C8—C7	−27.9 (3)	C1—C6—C5—C4	0.0 (4)
O3—C10—C8—C9	−26.2 (4)	C7—C6—C5—C4	179.3 (2)
O4—C10—C8—C9	154.2 (2)	C6—C5—C4—C3	1.0 (4)
C1—O1—C9—O2	179.5 (2)	C2—C3—C4—C5	−0.6 (4)
C1—O1—C9—C8	−3.3 (3)	O5—C14—C15—C16	−178.4 (2)
C7—C8—C9—O2	178.4 (3)	C13—C14—C15—C16	0.5 (4)
C10—C8—C9—O2	−3.8 (4)	C14—C15—C16—C11	−0.8 (4)
C7—C8—C9—O1	1.6 (3)	C12—C11—C16—C15	0.6 (4)
C10—C8—C9—O1	179.4 (2)	O4—C11—C16—C15	174.4 (2)
C9—O1—C1—C2	−177.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C6/C7/C8/C9/O1 and C1/C2/C3/C4/C5/C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O5ⁱ	0.96	2.50	3.228 (3)	132
C12—H12···O2ⁱⁱ	0.93	2.48	3.353 (3)	156
C15—H15···O2ⁱⁱⁱ	0.93	2.50	3.207 (3)	133
C3—H3···O3^iv	0.93	2.47	3.272 (4)	145
C5—H5···Cg1^v	0.93	2.82	3.303 (3)	114
C17—H17C···Cg2^vi	0.93	2.96	3.709 (4)	136

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C6/C7/C8/C9/O1 and C1/C2/C3/C4/C5/C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O5ⁱ	0.96	2.50	3.228 (3)	132
C12—H12···O2ⁱⁱ	0.93	2.48	3.353 (3)	156
C15—H15···O2ⁱⁱⁱ	0.93	2.50	3.207 (3)	133
C3—H3···O3^iv	0.93	2.47	3.272 (4)	145
C5—H5···Cg1^v	0.93	2.82	3.303 (3)	114
C17—H17C···Cg2^vi	0.93	2.96	3.709 (4)	136

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

Acknowledgements

BSP thanks Dr Biraj, Sophisticated Analytical Instrumentation Centre (SAIC), Tezpur University, Assam, for his help in data collection and UGC, Government of India, for financial support under Minor Research Project.

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Volume 71| Part 6| June 2015| Pages o374-o375

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