8-Hy­droxy-3,4-bis­(4-meth­oxy­phen­yl)-1H-isochromen-1-one

Mayakrishnan, S.; Arun, Y.; Maheswari, N.U.

doi:10.1107/S2414314617005351

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170535

https://doi.org/10.1107/S2414314617005351

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8-Hydroxy-3,4-bis(4-methoxyphenyl)-1H-isochromen-1-one

Sivakalai Mayakrishnan,^a Y. Arun ^a and Narayanan Uma Maheswari ^a ^*

^aOrganic & Bio-organic Chemistry, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: umanarayanclri@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 28 March 2017; accepted 10 April 2017; online 21 April 2017)

In the title compound, C₂₃H₁₈O₅, the two methoxy-substituted benzene rings are inclined to one another by 67.0 (2)° and to the mean plane of the 1H-isochromene ring system by 67.21 (16) and 27.61 (17)°. There is an intramolecular C—H⋯π interaction present involving the two 4-methoxyphenyl rings. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming chains propagating along the [301] direction. The chains are linked by a number of C—H⋯π interactions, forming a three-dimensional structure.

Keywords: crystal structure; chromene; 1H-isochromen-1-one; hydrogen bonding.

CCDC reference: 1540578

Structure description

Chromene derivatives are important heterocyclic compounds that have a variety of industrial, biological and chemical synthesis applications (Geen et al., 1996 ; Ercole et al., 2009 ). They exhibit a number of pharmacological activities, such as anti-HIV, anti-inflammatory, antibacterial, anti-allergic and anticancer (Khan et al., 2010 ; Raj et al., 2010 ).

The title compound, Fig. 1, consists of a chromene moiety substituted by two methoxyphenyl groups and an hydroxy group. The two benzene rings (C10–C15 and C17–C22) are inclined to one another by 67.0 (2)° and to the mean plane of the 1H-isochromene ring system (O1/C1–C9) by 67.21 (16) and 27.61 (17)°, respectively. The 1H-isochromene moiety is planar (r.m.s. deviation = 0.043 Å) and atoms O2 and O3 deviate from this mean plane by −0.121 (3) and 0.058 (5) Å, respectively. There is an intramolecular C—H⋯π interaction present involving the two 4-methoxyphenyl rings (Table 1 and Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of benzene rings C10–C15 and C17–C22, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5ⁱ	0.82	2.56	3.236 (5)	140
C18—H18⋯Cg3	0.93	2.77	3.494 (5)	135
C3—H3⋯Cg3ⁱⁱ	0.93	2.79	3.611 (5)	148
C11—H11⋯Cg4ⁱⁱⁱ	0.93	2.73	3.593 (4)	155
C23—H23C⋯Cg4^iv	0.96	3.00	3.872 (7)	152
Symmetry codes: (i) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+3, -y, -z+1; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1.

Figure 1
The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular C—H⋯π interaction (Table 1

) is shown as a dashed arrow.

In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming chains propagating along [301]; Table 1 and Fig. 2. The chains are linked by a number of C—H⋯π interactions, forming a three-dimensional structure

Figure 2
A view along the a axis of the crystal packing of the title compound. The dashed lines represent the hydrogen bonds (see Table 1

). For clarity, H atoms not involved in hydrogen bonding have been omitted.

Synthesis and crystallization

To a dried 50 ml round-bottom flask, fitted with a reflux condenser, were added 2-hydroxybenzoic acid (0.3 mmol), 1,2-bis(4-methoxyphenyl)ethyne (0.3 mmol), [RuCl₂(p-cymene)] (5.0 mol %), AgOAc (1.0 equiv) and AgSbF₆ (20 mol %) in 1,2-dichloroethane. The reaction mixture was refluxed for 12 h. After cooling to ambient temperature, the reaction mixture was diluted with CH₂Cl₂, filtered through Celite and the filtrate was concentrated under reduced pressure. The crude product was purified through a silica gel column using hexane and ethyl acetate as eluent. The title compound was obtained in 65% yield. It was recrystallized by slow evaporation of a solution in chloroform, yielding colourless block-like crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₈O₅
M_r	374.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.8882 (7), 16.418 (3), 18.894 (3)
β (°)	95.016 (5)
V (Å³)	1819.5 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.976, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	9449, 2910, 1375
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.197, 1.01
No. of reflections	2910
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 SHELXL97 and SHELXTL (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1540578

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617005351/su4147sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005351/su4147Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005351/su4147Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

8-Hydroxy-3,4-bis(4-methoxyphenyl)-1H-isochromen-1-one top

Crystal data top

C₂₃H₁₈O₅	F(000) = 784
M_r = 374.37	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1375 reflections
a = 5.8882 (7) Å	θ = 2.2–24.2°
b = 16.418 (3) Å	µ = 0.10 mm⁻¹
c = 18.894 (3) Å	T = 296 K
β = 95.016 (5)°	Block, colourless
V = 1819.5 (5) Å³	0.25 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	2910 independent reflections
Radiation source: fine-focus sealed tube	1375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω and φ scans	θ_max = 24.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −6→4
T_min = 0.976, T_max = 0.985	k = −15→18
9449 measured reflections	l = −21→21

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.197	w = 1/[σ²(F_o²) + (0.0901P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2910 reflections	Δρ_max = 0.29 e Å⁻³
257 parameters	Δρ_min = −0.23 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: 0.006 (2)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.4796 (7)	0.1453 (3)	0.6993 (2)	0.0573 (12)
C2	1.6348 (7)	0.0900 (3)	0.6765 (2)	0.0606 (12)
H2	1.7539	0.0716	0.7081	0.073*
C3	1.6147 (6)	0.0621 (3)	0.6080 (2)	0.0583 (12)
H3	1.7190	0.0243	0.5936	0.070*
C4	1.4399 (6)	0.0896 (2)	0.55963 (19)	0.0490 (11)
H4	1.4289	0.0704	0.5132	0.059*
C5	1.2825 (6)	0.1453 (2)	0.58020 (18)	0.0423 (10)
C6	1.1052 (6)	0.1788 (2)	0.52959 (18)	0.0420 (10)
C7	0.9648 (6)	0.2358 (3)	0.55146 (18)	0.0470 (10)
C8	1.1367 (7)	0.2303 (3)	0.6731 (2)	0.0594 (12)
C9	1.3006 (6)	0.1729 (2)	0.65103 (19)	0.0469 (10)
C10	1.0851 (5)	0.1492 (2)	0.45471 (18)	0.0433 (10)
C11	1.2498 (6)	0.1688 (2)	0.40897 (19)	0.0483 (11)
H11	1.3791	0.1975	0.4263	0.058*
C12	1.2242 (6)	0.1464 (3)	0.33848 (19)	0.0514 (11)
H12	1.3341	0.1612	0.3084	0.062*
C13	1.0352 (6)	0.1020 (3)	0.3123 (2)	0.0522 (11)
C14	0.8745 (6)	0.0802 (3)	0.3572 (2)	0.0586 (12)
H14	0.7480	0.0499	0.3401	0.070*
C15	0.9007 (6)	0.1033 (2)	0.4279 (2)	0.0527 (11)
H15	0.7918	0.0876	0.4580	0.063*
C16	0.8276 (8)	0.0444 (4)	0.2115 (2)	0.1003 (19)
H16A	0.8093	−0.0066	0.2352	0.150*
H16B	0.8410	0.0347	0.1619	0.150*
H16C	0.6973	0.0783	0.2168	0.150*
C17	0.7859 (6)	0.2841 (2)	0.5105 (2)	0.0508 (11)
C18	0.7925 (7)	0.3006 (3)	0.4386 (2)	0.0651 (13)
H18	0.9111	0.2796	0.4147	0.078*
C19	0.6284 (8)	0.3471 (3)	0.4019 (3)	0.0772 (14)
H19	0.6361	0.3570	0.3537	0.093*
C20	0.4544 (8)	0.3789 (3)	0.4359 (3)	0.0720 (14)
C21	0.4392 (6)	0.3655 (3)	0.5068 (3)	0.0709 (14)
H21	0.3202	0.3878	0.5297	0.085*
C22	0.6072 (7)	0.3173 (3)	0.5446 (2)	0.0628 (12)
H22	0.5985	0.3076	0.5927	0.075*
C23	0.1536 (9)	0.4761 (4)	0.4247 (4)	0.126 (2)
H23A	0.0418	0.4439	0.4461	0.189*
H23B	0.0787	0.5117	0.3898	0.189*
H23C	0.2381	0.5079	0.4607	0.189*
O1	0.9793 (4)	0.26094 (17)	0.62196 (13)	0.0592 (8)
O2	1.1211 (5)	0.2567 (2)	0.73262 (15)	0.0907 (12)
O3	1.5022 (7)	0.1731 (3)	0.76879 (19)	0.1251 (15)
H3A	1.6270	0.1594	0.7878	0.188*
O4	1.0245 (5)	0.08343 (19)	0.24135 (14)	0.0747 (10)
O5	0.2996 (6)	0.4257 (2)	0.3928 (2)	0.1062 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.067 (3)	0.066 (3)	0.038 (2)	−0.002 (2)	−0.003 (2)	−0.014 (2)
C2	0.063 (2)	0.066 (3)	0.050 (3)	0.007 (2)	−0.007 (2)	−0.001 (2)
C3	0.059 (2)	0.054 (3)	0.062 (3)	0.009 (2)	0.007 (2)	0.005 (2)
C4	0.055 (2)	0.052 (3)	0.040 (2)	−0.005 (2)	0.0045 (19)	0.000 (2)
C5	0.050 (2)	0.035 (3)	0.042 (2)	−0.006 (2)	0.0065 (18)	−0.0031 (19)
C6	0.044 (2)	0.044 (3)	0.039 (2)	−0.0020 (19)	0.0070 (17)	−0.0011 (19)
C7	0.051 (2)	0.052 (3)	0.038 (2)	−0.007 (2)	0.0047 (18)	−0.007 (2)
C8	0.066 (3)	0.061 (3)	0.051 (3)	0.000 (2)	0.004 (2)	−0.001 (2)
C9	0.052 (2)	0.049 (3)	0.040 (2)	0.001 (2)	0.0012 (18)	−0.0017 (19)
C10	0.042 (2)	0.046 (3)	0.042 (2)	−0.0021 (19)	0.0036 (17)	0.0012 (19)
C11	0.046 (2)	0.049 (3)	0.049 (2)	−0.0093 (19)	0.0027 (18)	0.001 (2)
C12	0.054 (2)	0.058 (3)	0.043 (2)	−0.007 (2)	0.0113 (18)	0.007 (2)
C13	0.054 (2)	0.059 (3)	0.043 (2)	0.000 (2)	−0.001 (2)	−0.004 (2)
C14	0.052 (2)	0.068 (3)	0.054 (3)	−0.017 (2)	−0.004 (2)	−0.008 (2)
C15	0.048 (2)	0.063 (3)	0.048 (3)	−0.011 (2)	0.0079 (18)	−0.001 (2)
C16	0.112 (4)	0.120 (5)	0.065 (3)	−0.021 (4)	−0.013 (3)	−0.026 (3)
C17	0.049 (2)	0.039 (3)	0.064 (3)	−0.005 (2)	0.002 (2)	−0.002 (2)
C18	0.060 (3)	0.067 (4)	0.067 (3)	0.000 (2)	−0.001 (2)	0.017 (3)
C19	0.071 (3)	0.076 (4)	0.082 (3)	−0.006 (3)	−0.007 (3)	0.011 (3)
C20	0.067 (3)	0.054 (3)	0.090 (4)	−0.005 (3)	−0.025 (3)	0.009 (3)
C21	0.046 (2)	0.058 (4)	0.107 (4)	−0.005 (2)	−0.006 (3)	−0.020 (3)
C22	0.066 (3)	0.054 (3)	0.068 (3)	−0.008 (2)	0.004 (2)	−0.005 (2)
C23	0.084 (4)	0.080 (5)	0.207 (7)	0.014 (4)	−0.026 (4)	−0.037 (5)
O1	0.0656 (17)	0.061 (2)	0.0511 (18)	0.0081 (15)	0.0062 (14)	−0.0058 (15)
O2	0.109 (2)	0.113 (3)	0.0491 (19)	0.037 (2)	0.0023 (17)	−0.0251 (19)
O3	0.136 (3)	0.156 (4)	0.079 (3)	0.016 (3)	−0.015 (2)	−0.019 (3)
O4	0.083 (2)	0.095 (3)	0.0435 (18)	−0.0101 (18)	−0.0063 (14)	−0.0165 (16)
O5	0.085 (2)	0.096 (3)	0.131 (3)	0.010 (2)	−0.028 (2)	0.003 (2)

Geometric parameters (Å, º) top

C1—C2	1.383 (5)	C13—C14	1.372 (5)
C1—O3	1.386 (5)	C14—C15	1.384 (5)
C1—C9	1.407 (5)	C14—H14	0.9300
C2—C3	1.369 (5)	C15—H15	0.9300
C2—H2	0.9300	C16—O4	1.400 (5)
C3—C4	1.391 (5)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.382 (5)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18	1.389 (5)
C5—C9	1.408 (5)	C17—C22	1.392 (5)
C5—C6	1.460 (5)	C18—C19	1.371 (6)
C6—C7	1.338 (5)	C18—H18	0.9300
C6—C10	1.491 (5)	C19—C20	1.359 (6)
C7—O1	1.390 (4)	C19—H19	0.9300
C7—C17	1.482 (5)	C20—C21	1.369 (6)
C8—O2	1.216 (4)	C20—O5	1.398 (5)
C8—O1	1.374 (4)	C21—C22	1.411 (6)
C8—C9	1.436 (6)	C21—H21	0.9300
C10—C15	1.381 (5)	C22—H22	0.9300
C10—C11	1.392 (5)	C23—O5	1.370 (6)
C11—C12	1.377 (5)	C23—H23A	0.9600
C11—H11	0.9300	C23—H23B	0.9600
C12—C13	1.385 (5)	C23—H23C	0.9600
C12—H12	0.9300	O3—H3A	0.8200
C13—O4	1.371 (4)

C2—C1—O3	119.9 (4)	C13—C14—H14	120.0
C2—C1—C9	119.2 (4)	C15—C14—H14	120.0
O3—C1—C9	120.8 (4)	C10—C15—C14	121.4 (4)
C3—C2—C1	120.6 (4)	C10—C15—H15	119.3
C3—C2—H2	119.7	C14—C15—H15	119.3
C1—C2—H2	119.7	O4—C16—H16A	109.5
C2—C3—C4	120.7 (4)	O4—C16—H16B	109.5
C2—C3—H3	119.6	H16A—C16—H16B	109.5
C4—C3—H3	119.6	O4—C16—H16C	109.5
C5—C4—C3	120.4 (4)	H16A—C16—H16C	109.5
C5—C4—H4	119.8	H16B—C16—H16C	109.5
C3—C4—H4	119.8	C18—C17—C22	117.6 (4)
C4—C5—C9	118.9 (3)	C18—C17—C7	122.4 (4)
C4—C5—C6	121.6 (3)	C22—C17—C7	119.9 (4)
C9—C5—C6	119.5 (3)	C19—C18—C17	121.5 (4)
C7—C6—C5	119.1 (3)	C19—C18—H18	119.2
C7—C6—C10	121.4 (3)	C17—C18—H18	119.2
C5—C6—C10	119.5 (3)	C20—C19—C18	120.2 (5)
C6—C7—O1	121.1 (3)	C20—C19—H19	119.9
C6—C7—C17	130.0 (3)	C18—C19—H19	119.9
O1—C7—C17	108.9 (3)	C19—C20—C21	121.2 (4)
O2—C8—O1	114.8 (4)	C19—C20—O5	114.6 (5)
O2—C8—C9	127.5 (4)	C21—C20—O5	124.2 (5)
O1—C8—C9	117.7 (4)	C20—C21—C22	118.8 (4)
C1—C9—C5	120.1 (4)	C20—C21—H21	120.6
C1—C9—C8	120.5 (4)	C22—C21—H21	120.6
C5—C9—C8	119.3 (3)	C17—C22—C21	120.7 (4)
C15—C10—C11	117.8 (3)	C17—C22—H22	119.6
C15—C10—C6	121.4 (3)	C21—C22—H22	119.6
C11—C10—C6	120.8 (3)	O5—C23—H23A	109.5
C12—C11—C10	121.1 (3)	O5—C23—H23B	109.5
C12—C11—H11	119.5	H23A—C23—H23B	109.5
C10—C11—H11	119.5	O5—C23—H23C	109.5
C11—C12—C13	120.1 (3)	H23A—C23—H23C	109.5
C11—C12—H12	119.9	H23B—C23—H23C	109.5
C13—C12—H12	119.9	C8—O1—C7	123.1 (3)
O4—C13—C14	124.8 (3)	C1—O3—H3A	109.5
O4—C13—C12	115.6 (3)	C13—O4—C16	117.5 (3)
C14—C13—C12	119.5 (3)	C23—O5—C20	118.6 (5)
C13—C14—C15	120.0 (3)

O3—C1—C2—C3	−179.9 (4)	C6—C10—C11—C12	−175.5 (4)
C9—C1—C2—C3	−0.2 (6)	C10—C11—C12—C13	−1.6 (6)
C1—C2—C3—C4	0.9 (6)	C11—C12—C13—O4	179.4 (4)
C2—C3—C4—C5	−0.4 (6)	C11—C12—C13—C14	−0.3 (6)
C3—C4—C5—C9	−0.8 (6)	O4—C13—C14—C15	−179.0 (4)
C3—C4—C5—C6	176.4 (3)	C12—C13—C14—C15	0.7 (6)
C4—C5—C6—C7	−176.4 (4)	C11—C10—C15—C14	−2.6 (6)
C9—C5—C6—C7	0.8 (5)	C6—C10—C15—C14	175.8 (4)
C4—C5—C6—C10	3.2 (5)	C13—C14—C15—C10	0.8 (6)
C9—C5—C6—C10	−179.6 (3)	C6—C7—C17—C18	−26.0 (6)
C5—C6—C7—O1	−2.8 (5)	O1—C7—C17—C18	151.4 (4)
C10—C6—C7—O1	177.6 (3)	C6—C7—C17—C22	156.4 (4)
C5—C6—C7—C17	174.4 (3)	O1—C7—C17—C22	−26.2 (5)
C10—C6—C7—C17	−5.3 (6)	C22—C17—C18—C19	−0.6 (6)
C2—C1—C9—C5	−1.0 (6)	C7—C17—C18—C19	−178.3 (4)
O3—C1—C9—C5	178.8 (4)	C17—C18—C19—C20	0.4 (7)
C2—C1—C9—C8	−180.0 (4)	C18—C19—C20—C21	0.2 (7)
O3—C1—C9—C8	−0.3 (6)	C18—C19—C20—O5	179.5 (4)
C4—C5—C9—C1	1.4 (6)	C19—C20—C21—C22	−0.5 (7)
C6—C5—C9—C1	−175.8 (3)	O5—C20—C21—C22	−179.7 (4)
C4—C5—C9—C8	−179.5 (4)	C18—C17—C22—C21	0.3 (6)
C6—C5—C9—C8	3.2 (5)	C7—C17—C22—C21	178.0 (4)
O2—C8—C9—C1	−5.2 (7)	C20—C21—C22—C17	0.2 (6)
O1—C8—C9—C1	173.9 (3)	O2—C8—O1—C7	−177.5 (4)
O2—C8—C9—C5	175.8 (4)	C9—C8—O1—C7	3.4 (5)
O1—C8—C9—C5	−5.2 (6)	C6—C7—O1—C8	0.7 (5)
C7—C6—C10—C15	−68.8 (5)	C17—C7—O1—C8	−177.0 (3)
C5—C6—C10—C15	111.6 (4)	C14—C13—O4—C16	4.8 (6)
C7—C6—C10—C11	109.6 (4)	C12—C13—O4—C16	−174.9 (4)
C5—C6—C10—C11	−70.0 (5)	C19—C20—O5—C23	−164.1 (5)
C15—C10—C11—C12	3.0 (6)	C21—C20—O5—C23	15.2 (7)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of benzene rings C10–C15 and C17–C22, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5ⁱ	0.82	2.56	3.236 (5)	140
C18—H18···Cg3	0.93	2.77	3.494 (5)	135
C3—H3···Cg3ⁱⁱ	0.93	2.79	3.611 (5)	148
C11—H11···Cg4ⁱⁱⁱ	0.93	2.73	3.593 (4)	155
C23—H23C···Cg4^iv	0.96	3.00	3.872 (7)	152

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

Acknowledgements

The authors thank the Department of Chemistry, IIT, Chennai, India, for the X-ray intensity data collection.

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