2,2′-[(4-But­oxy­phen­yl)methyl­ene]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one)

Suresh Babu, N.; Anbu Chudar Azhagan, S.; Loganathan, B.; Sughanya, V.; Ayyappan, J.

doi:10.1107/S2414314625001804

organic compounds

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ISSN: 2414-3146

Volume 10| Part 2| February 2025| x250180

https://doi.org/10.1107/S2414314625001804

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2,2′-[(4-Butoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

N. Suresh Babu,^a ^* S. Anbu Chudar Azhagan,^b B. Loganathan,^c V. Sughanya ^d and J. Ayyappan ^e

^aDepartment of Chemistry, Government College of Engineering, Tirunelveli-627 007, Tamilnadu, India, ^bDepartment of Physics, Government College of Engineering, Tirunelveli-627 007, Tamilnadu, India, ^cDepartment of Chemistry (Science and Humanities), Dr. N. G. P. Institute of Technology, Coimbatore-641 048, Tamil Nadu, India, ^dDepartment of Chemistry, Periyar Government Arts College, Cuddalore-607 001., Tamil Nadu, India, and ^eDepartment of Physics, Government College of Engineering, Salem-636 011, Tamilnadu, India
^*Correspondence e-mail: babusuresh1982@gmail.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 14 February 2025; accepted 25 February 2025; online 28 February 2025)

In the title compound, C₂₇H₃₆O₅, the dihedral angles between the planes of the benzene ring and the cyclohexenone rings are 60.87 (10) and 65.04 (10)°, while the dihedral angle between the mean planes of the two cyclohexenone rings is 39.33 (10)°. Each cyclohexenone ring has a carbon atom bonded to two methyl groups, which acts as the flap atom, resulting in an envelope conformation. The opposite orientation of the hydroxy and carbonyl oxygen atoms allows for the formation of two intramolecular O—H⋯O hydrogen bonds and C—H⋯π (ring) interactions also help to establish the molecular conformation.

Keywords: crystal structure; 4-butoxybenzaldehyde; dimedone; xanthene; C—H⋯π (ring) interaction; hydrogen bond.

CCDC reference: 2421922

Structure description

Xanthene derivatives possess biological properties such as antiviral, antibacterial (Dimmock et al., 1988 ) and anti-inflammatory (Dimmock et al., 1988; Cottam et al., 1996 ) activities and are therefore used in medicine. Xanthene is present in organic compounds that are widely used as synthetic dyes (Hilderbrand et al., 2007 ), in laser technologies (Pohlers et al., 1997 ) and in fluorescent materials used for visualization of biomolecules (Knight & Stephens, 1989 ; Khan & Sekar, 2023 ; Majumdar et al., 2022 ; Lakhrissi et al., 2022 ).

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987 ) and angles are close to those reported for similar compounds (for examples, see: Sureshbabu & Sughanya, 2012 , 2013 ; Sughanya & Sureshbabu, 2012 ; Khalilov et al., 2023 ; Steiger et al., 2020 ). In the cyclohexenone ring, C1—C6 and C8—C13 are double bonds, as indicated by the bond lengths [1.380 (2) and 1.374 (2) Å, respectively]. The observed carbonyl bond lengths [C5—O1 = 1.270 (2) and C9—O3 = 1.268 (2) Å] are also normal. Cyclohexenone rings A (C1–C6) and B (C8–C13) are not planar with total puckering amplitudes Q(T) of 0.466 (2) Å (for A) and 0.472 (2) Å (for B). Atoms C3 and C11 act as the flap atoms in the envelope conformations of cyclohexenone rings A and B, deviating from the mean planes of the rings by 0.325 (2) and 0.327 (2) Å, respectively. The observed conformations can be described by the puckering parameters (Cremer & Pople, 1975 ), which yield values of φ = 122.3 (3)° and θ = 63.5 (2)° for ring A and φ = 186.8 (3)° and θ = 63.5 (2)° for ring B. Ring A and B make dihedral angles of 60.87 (10) and 65.04 (10)°, respectively, with the benzene ring. The dihedral angle between the mean planes of the cyclohexenone rings is 39.33 (10)°.

Figure 1
The molecular structure of the title compound showing the atom-numbering scheme and intramolecular O—H⋯O hydrogen bonds as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

The structure features two intramolecular O—H⋯O hydrogen bonds (Fig. 1, Table 1). The relatively short H⋯A distances and the near-linear D—H⋯A angles suggest that these are strong hydrogen bonds. An intermolecular C10—H10B⋯π(C18–C22) interaction is also observed (Fig. 2, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.92 (2)	1.66 (2)	2.566 (2)	166 (3)
O4—H4⋯O1	0.94 (3)	1.72 (3)	2.655 (2)	171 (3)
C10—H10B⋯Cg1ⁱ	0.97	3.11	3.773 (2)	127
Symmetry code: (i) .

Figure 2
A view of the packing in the crystal structure, showing the O—H⋯O hydrogen bonds and C—H⋯π interactions as dashed lines.

Synthesis and crystallization

The title compound was prepared in a single stage as previously described (Horning & Horning, 1946 ; Kaupp et al. 2003 ). A mixture consisting of 4-butoxybenzaldehyde (0.712 g, 4 mmol), 5,5-dimethylcyclohexane-1,3-dione (1.12 g, 8 mmol) and 15 ml of ethanol was heated at 343 K for approximately 5 minutes. The reaction mixture was allowed to cool to room temperature and the resulting title compound was filtered and dried. Colourless crystal were obtained by crystallization from ethanol solution at room temperature, m.p. 401 K, yield 1.65 g (3.75 mmol, 94%).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₇H₃₆O₅
M_r	440.56
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	10.3372 (14), 11.3286 (15), 12.4559 (16)
α, β, γ (°)	105.428 (7), 114.185 (7), 97.344 (8)
V (Å³)	1235.3 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.15 × 0.12

Data collection
Diffractometer	Bruker kappa APEXII
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.904, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	29655, 6476, 3194
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.680

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.145, 1.02
No. of reflections	6476
No. of parameters	303
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ), publCIF (Westrip, 2010 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2421922

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625001804/vm4064sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625001804/vm4064Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625001804/vm4064Isup3.cml

checkCIF report

Computing details top

2,2'-[(4-Butoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) top

Crystal data top

C₂₇H₃₆O₅	F(000) = 476
M_r = 440.56	D_x = 1.184 Mg m⁻³
Triclinic, P1	Melting point: 401 K
a = 10.3372 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3286 (15) Å	Cell parameters from 4681 reflections
c = 12.4559 (16) Å	θ = 2.2–23.3°
α = 105.428 (7)°	µ = 0.08 mm⁻¹
β = 114.185 (7)°	T = 296 K
γ = 97.344 (8)°	BLOCK, colourless
V = 1235.3 (3) Å³	0.20 × 0.15 × 0.12 mm
Z = 2

Data collection top

Bruker kappa APEXII diffractometer	6476 independent reflections
Radiation source: fine-focus sealed tube	3194 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ω and φ scan	θ_max = 28.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015 )	h = −14→14
T_min = 0.904, T_max = 0.983	k = −15→15
29655 measured reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0478P)² + 0.1871P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.19 e Å⁻³
6476 reflections	Δρ_min = −0.15 e Å⁻³
303 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.109 (4)

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. All hydrogen atoms were identified from difference in electron density peaks and subsequently treated as riding atoms with d(Csp2 —H) = 0.93 Å, d(Cmethyl—H) = 0.96 Å, d(Cmethylene—H) = 0.97 Å, d(Cmethine—H) = 0.98 Å, d(O—H) = 0.82 Å, and U_iso(H) = xU_eq(C,O), where x = 1.5 for methyl H and 1.2 for all other H atoms.

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

	x	y	z	U_iso*/U_eq
C1	0.9540 (2)	0.64151 (17)	0.87672 (17)	0.0410 (4)
C2	1.1067 (2)	0.63643 (19)	0.95588 (18)	0.0522 (5)
H2A	1.163770	0.643254	0.911360	0.063*
H2B	1.101053	0.553939	0.965337	0.063*
C3	1.1885 (2)	0.73860 (18)	1.08581 (17)	0.0474 (5)
C4	1.0844 (2)	0.74257 (19)	1.14393 (17)	0.0497 (5)
H4A	1.074848	0.667597	1.166673	0.060*
H4B	1.128142	0.816283	1.220730	0.060*
C5	0.9334 (2)	0.74828 (18)	1.06066 (17)	0.0442 (5)
C6	0.87642 (19)	0.70583 (16)	0.92811 (16)	0.0367 (4)
C7	0.73019 (18)	0.72894 (16)	0.85046 (15)	0.0361 (4)
H7	0.719136	0.795891	0.911993	0.043*
C8	0.59514 (19)	0.61938 (17)	0.80092 (16)	0.0372 (4)
C9	0.5451 (2)	0.51703 (17)	0.68598 (16)	0.0390 (4)
C10	0.4007 (2)	0.42026 (19)	0.62870 (18)	0.0485 (5)
H10A	0.419450	0.342368	0.642254	0.058*
H10B	0.353068	0.401903	0.538652	0.058*
C11	0.2941 (2)	0.45827 (19)	0.67898 (19)	0.0521 (5)
C12	0.3821 (2)	0.5133 (2)	0.82193 (19)	0.0552 (6)
H12A	0.320767	0.549349	0.855828	0.066*
H12B	0.405858	0.444667	0.852679	0.066*
C13	0.5216 (2)	0.61327 (18)	0.87035 (18)	0.0444 (5)
C14	1.2354 (2)	0.86802 (19)	1.0768 (2)	0.0582 (6)
H14A	1.296929	0.862935	1.036209	0.087*
H14B	1.288990	0.931057	1.159736	0.087*
H14C	1.149520	0.891156	1.028790	0.087*
C15	1.3263 (2)	0.7069 (2)	1.1670 (2)	0.0706 (7)
H15A	1.299016	0.625870	1.173580	0.106*
H15B	1.375905	0.771208	1.249396	0.106*
H15C	1.390873	0.703723	1.129299	0.106*
C16	0.2257 (2)	0.5560 (2)	0.6272 (2)	0.0746 (7)
H16A	0.302038	0.631312	0.653908	0.112*
H16B	0.157509	0.577284	0.658149	0.112*
H16C	0.174873	0.520770	0.536970	0.112*
C17	0.1702 (3)	0.3414 (2)	0.6390 (2)	0.0774 (7)
H17A	0.104120	0.365868	0.671439	0.116*
H17B	0.211193	0.279550	0.671525	0.116*
H17C	0.117397	0.305452	0.548877	0.116*
C18	0.72888 (19)	0.78827 (16)	0.75292 (15)	0.0361 (4)
C19	0.8561 (2)	0.84862 (18)	0.75624 (18)	0.0461 (5)
H19	0.946390	0.844951	0.813861	0.055*
C20	0.8535 (2)	0.91443 (19)	0.67650 (18)	0.0486 (5)
H20	0.940970	0.952848	0.680025	0.058*
C21	0.7207 (2)	0.92277 (17)	0.59181 (17)	0.0415 (4)
C22	0.5921 (2)	0.86339 (18)	0.58710 (17)	0.0447 (5)
H22	0.501922	0.867947	0.530217	0.054*
C23	0.5972 (2)	0.79769 (17)	0.66614 (17)	0.0427 (5)
H23	0.509472	0.758152	0.661380	0.051*
C24	0.8338 (2)	1.0409 (2)	0.50532 (19)	0.0535 (5)
H24A	0.882600	0.975976	0.488203	0.064*
H24B	0.901890	1.107137	0.585082	0.064*
C25	0.7873 (2)	1.0956 (2)	0.40203 (19)	0.0562 (6)
H25A	0.874610	1.143573	0.405629	0.067*
H25B	0.730690	1.154325	0.416725	0.067*
C26	0.6965 (3)	0.9969 (3)	0.2723 (2)	0.0763 (7)
H26A	0.748689	0.933122	0.260941	0.092*
H26B	0.604385	0.955028	0.265916	0.092*
C27	0.6634 (4)	1.0494 (3)	0.1690 (2)	0.1080 (11)
H27A	0.605640	1.108246	0.175882	0.162*
H27B	0.609445	0.981267	0.089307	0.162*
H27C	0.753938	1.092567	0.175443	0.162*
O1	0.85854 (16)	0.78933 (15)	1.11437 (12)	0.0619 (4)
O2	0.90380 (16)	0.58030 (14)	0.75734 (12)	0.0548 (4)
O3	0.62230 (14)	0.50085 (12)	0.62903 (11)	0.0487 (4)
O4	0.56851 (17)	0.69215 (15)	0.98548 (13)	0.0604 (4)
O5	0.70516 (14)	0.98724 (14)	0.51060 (13)	0.0573 (4)
H2	0.803 (2)	0.565 (3)	0.712 (2)	0.120 (11)*
H4	0.670 (2)	0.733 (3)	1.027 (3)	0.167 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0403 (10)	0.0388 (10)	0.0392 (11)	0.0100 (9)	0.0156 (9)	0.0119 (9)
C2	0.0432 (11)	0.0483 (12)	0.0561 (13)	0.0174 (10)	0.0167 (10)	0.0131 (10)
C3	0.0404 (11)	0.0472 (12)	0.0458 (11)	0.0103 (9)	0.0112 (9)	0.0185 (9)
C4	0.0477 (12)	0.0509 (12)	0.0389 (11)	0.0065 (10)	0.0108 (9)	0.0167 (9)
C5	0.0458 (11)	0.0427 (11)	0.0396 (11)	0.0077 (9)	0.0179 (9)	0.0130 (9)
C6	0.0368 (10)	0.0368 (10)	0.0360 (10)	0.0098 (8)	0.0166 (8)	0.0128 (8)
C7	0.0376 (10)	0.0362 (10)	0.0361 (9)	0.0113 (8)	0.0186 (8)	0.0118 (8)
C8	0.0364 (10)	0.0402 (10)	0.0375 (10)	0.0114 (8)	0.0179 (8)	0.0157 (8)
C9	0.0399 (10)	0.0424 (11)	0.0387 (10)	0.0151 (9)	0.0169 (9)	0.0203 (9)
C10	0.0467 (12)	0.0465 (11)	0.0432 (11)	0.0066 (9)	0.0152 (9)	0.0141 (9)
C11	0.0420 (11)	0.0540 (13)	0.0588 (13)	0.0075 (10)	0.0222 (10)	0.0224 (11)
C12	0.0503 (12)	0.0594 (13)	0.0610 (13)	0.0085 (11)	0.0335 (11)	0.0192 (11)
C13	0.0427 (11)	0.0465 (11)	0.0455 (11)	0.0123 (9)	0.0224 (9)	0.0152 (9)
C14	0.0535 (13)	0.0541 (13)	0.0596 (13)	0.0060 (11)	0.0206 (11)	0.0218 (11)
C15	0.0518 (14)	0.0765 (16)	0.0712 (15)	0.0216 (12)	0.0114 (12)	0.0337 (13)
C16	0.0481 (13)	0.0781 (17)	0.0953 (18)	0.0214 (13)	0.0246 (13)	0.0393 (15)
C17	0.0583 (15)	0.0719 (16)	0.0874 (18)	−0.0091 (13)	0.0331 (14)	0.0201 (14)
C18	0.0346 (10)	0.0358 (10)	0.0381 (10)	0.0098 (8)	0.0166 (8)	0.0135 (8)
C19	0.0347 (10)	0.0563 (12)	0.0515 (12)	0.0145 (9)	0.0175 (9)	0.0281 (10)
C20	0.0375 (11)	0.0590 (13)	0.0595 (12)	0.0122 (10)	0.0259 (10)	0.0311 (11)
C21	0.0425 (11)	0.0449 (11)	0.0464 (11)	0.0148 (9)	0.0238 (9)	0.0235 (9)
C22	0.0347 (10)	0.0528 (12)	0.0494 (11)	0.0139 (9)	0.0173 (9)	0.0249 (10)
C23	0.0355 (10)	0.0475 (11)	0.0528 (11)	0.0118 (9)	0.0230 (9)	0.0247 (9)
C24	0.0457 (12)	0.0632 (13)	0.0572 (12)	0.0085 (10)	0.0265 (10)	0.0281 (11)
C25	0.0545 (13)	0.0630 (14)	0.0597 (13)	0.0095 (11)	0.0300 (11)	0.0316 (12)
C26	0.0772 (17)	0.0818 (17)	0.0590 (15)	0.0070 (14)	0.0231 (13)	0.0290 (13)
C27	0.124 (3)	0.133 (3)	0.0605 (16)	0.028 (2)	0.0300 (17)	0.0471 (18)
O1	0.0568 (9)	0.0804 (11)	0.0435 (8)	0.0159 (8)	0.0266 (7)	0.0101 (7)
O2	0.0475 (9)	0.0647 (9)	0.0419 (8)	0.0189 (8)	0.0187 (7)	0.0051 (7)
O3	0.0485 (8)	0.0567 (9)	0.0406 (7)	0.0150 (7)	0.0227 (6)	0.0131 (6)
O4	0.0600 (10)	0.0686 (10)	0.0498 (9)	0.0072 (8)	0.0345 (8)	0.0070 (8)
O5	0.0462 (8)	0.0777 (10)	0.0729 (10)	0.0231 (7)	0.0334 (7)	0.0513 (8)

Geometric parameters (Å, º) top

C1—O2	1.299 (2)	C15—H15A	0.9600
C1—C6	1.380 (2)	C15—H15B	0.9600
C1—C2	1.498 (3)	C15—H15C	0.9600
C2—C3	1.518 (3)	C16—H16A	0.9600
C2—H2A	0.9700	C16—H16B	0.9600
C2—H2B	0.9700	C16—H16C	0.9600
C3—C4	1.522 (3)	C17—H17A	0.9600
C3—C15	1.525 (3)	C17—H17B	0.9600
C3—C14	1.532 (3)	C17—H17C	0.9600
C4—C5	1.500 (3)	C18—C19	1.382 (2)
C4—H4A	0.9700	C18—C23	1.387 (2)
C4—H4B	0.9700	C19—C20	1.386 (2)
C5—O1	1.270 (2)	C19—H19	0.9300
C5—C6	1.419 (2)	C20—C21	1.381 (3)
C6—C7	1.526 (2)	C20—H20	0.9300
C7—C8	1.521 (2)	C21—O5	1.368 (2)
C7—C18	1.533 (2)	C21—C22	1.382 (2)
C7—H7	0.9800	C22—C23	1.372 (2)
C8—C13	1.374 (2)	C22—H22	0.9300
C8—C9	1.421 (2)	C23—H23	0.9300
C9—O3	1.268 (2)	C24—O5	1.424 (2)
C9—C10	1.494 (3)	C24—C25	1.504 (3)
C10—C11	1.528 (3)	C24—H24A	0.9700
C10—H10A	0.9700	C24—H24B	0.9700
C10—H10B	0.9700	C25—C26	1.507 (3)
C11—C12	1.524 (3)	C25—H25A	0.9700
C11—C17	1.528 (3)	C25—H25B	0.9700
C11—C16	1.533 (3)	C26—C27	1.491 (3)
C12—C13	1.494 (3)	C26—H26A	0.9700
C12—H12A	0.9700	C26—H26B	0.9700
C12—H12B	0.9700	C27—H27A	0.9600
C13—O4	1.314 (2)	C27—H27B	0.9600
C14—H14A	0.9600	C27—H27C	0.9600
C14—H14B	0.9600	O2—H2	0.927 (17)
C14—H14C	0.9600	O4—H4	0.942 (18)

O2—C1—C6	124.27 (17)	H14B—C14—H14C	109.5
O2—C1—C2	113.58 (16)	C3—C15—H15A	109.5
C6—C1—C2	122.16 (16)	C3—C15—H15B	109.5
C1—C2—C3	115.21 (16)	H15A—C15—H15B	109.5
C1—C2—H2A	108.5	C3—C15—H15C	109.5
C3—C2—H2A	108.5	H15A—C15—H15C	109.5
C1—C2—H2B	108.5	H15B—C15—H15C	109.5
C3—C2—H2B	108.5	C11—C16—H16A	109.5
H2A—C2—H2B	107.5	C11—C16—H16B	109.5
C2—C3—C4	107.34 (16)	H16A—C16—H16B	109.5
C2—C3—C15	110.27 (17)	C11—C16—H16C	109.5
C4—C3—C15	110.01 (17)	H16A—C16—H16C	109.5
C2—C3—C14	110.52 (17)	H16B—C16—H16C	109.5
C4—C3—C14	110.38 (17)	C11—C17—H17A	109.5
C15—C3—C14	108.32 (17)	C11—C17—H17B	109.5
C5—C4—C3	114.71 (15)	H17A—C17—H17B	109.5
C5—C4—H4A	108.6	C11—C17—H17C	109.5
C3—C4—H4A	108.6	H17A—C17—H17C	109.5
C5—C4—H4B	108.6	H17B—C17—H17C	109.5
C3—C4—H4B	108.6	C19—C18—C23	116.65 (16)
H4A—C4—H4B	107.6	C19—C18—C7	122.81 (15)
O1—C5—C6	122.08 (17)	C23—C18—C7	120.03 (15)
O1—C5—C4	116.78 (16)	C18—C19—C20	122.14 (17)
C6—C5—C4	121.10 (17)	C18—C19—H19	118.9
C1—C6—C5	117.87 (16)	C20—C19—H19	118.9
C1—C6—C7	123.85 (15)	C21—C20—C19	119.76 (17)
C5—C6—C7	118.23 (15)	C21—C20—H20	120.1
C8—C7—C6	114.91 (14)	C19—C20—H20	120.1
C8—C7—C18	113.69 (14)	O5—C21—C20	124.82 (16)
C6—C7—C18	115.36 (14)	O5—C21—C22	116.12 (16)
C8—C7—H7	103.6	C20—C21—C22	119.05 (17)
C6—C7—H7	103.6	C23—C22—C21	120.18 (17)
C18—C7—H7	103.6	C23—C22—H22	119.9
C13—C8—C9	117.57 (17)	C21—C22—H22	119.9
C13—C8—C7	120.39 (16)	C22—C23—C18	122.21 (17)
C9—C8—C7	121.95 (15)	C22—C23—H23	118.9
O3—C9—C8	121.85 (17)	C18—C23—H23	118.9
O3—C9—C10	116.66 (16)	O5—C24—C25	107.97 (16)
C8—C9—C10	121.46 (16)	O5—C24—H24A	110.1
C9—C10—C11	115.37 (16)	C25—C24—H24A	110.1
C9—C10—H10A	108.4	O5—C24—H24B	110.1
C11—C10—H10A	108.4	C25—C24—H24B	110.1
C9—C10—H10B	108.4	H24A—C24—H24B	108.4
C11—C10—H10B	108.4	C24—C25—C26	113.79 (19)
H10A—C10—H10B	107.5	C24—C25—H25A	108.8
C12—C11—C10	107.03 (16)	C26—C25—H25A	108.8
C12—C11—C17	109.85 (17)	C24—C25—H25B	108.8
C10—C11—C17	109.92 (18)	C26—C25—H25B	108.8
C12—C11—C16	110.96 (18)	H25A—C25—H25B	107.7
C10—C11—C16	110.65 (18)	C27—C26—C25	113.9 (2)
C17—C11—C16	108.43 (18)	C27—C26—H26A	108.8
C13—C12—C11	114.12 (16)	C25—C26—H26A	108.8
C13—C12—H12A	108.7	C27—C26—H26B	108.8
C11—C12—H12A	108.7	C25—C26—H26B	108.8
C13—C12—H12B	108.7	H26A—C26—H26B	107.7
C11—C12—H12B	108.7	C26—C27—H27A	109.5
H12A—C12—H12B	107.6	C26—C27—H27B	109.5
O4—C13—C8	123.47 (17)	H27A—C27—H27B	109.5
O4—C13—C12	114.02 (16)	C26—C27—H27C	109.5
C8—C13—C12	122.49 (17)	H27A—C27—H27C	109.5
C3—C14—H14A	109.5	H27B—C27—H27C	109.5
C3—C14—H14B	109.5	C1—O2—H2	113.2 (18)
H14A—C14—H14B	109.5	C13—O4—H4	113 (2)
C3—C14—H14C	109.5	C21—O5—C24	117.78 (14)
H14A—C14—H14C	109.5

O2—C1—C2—C3	160.74 (17)	C9—C10—C11—C12	−46.3 (2)
C6—C1—C2—C3	−19.2 (3)	C9—C10—C11—C17	−165.60 (18)
C1—C2—C3—C4	47.6 (2)	C9—C10—C11—C16	74.7 (2)
C1—C2—C3—C15	167.44 (18)	C10—C11—C12—C13	50.3 (2)
C1—C2—C3—C14	−72.8 (2)	C17—C11—C12—C13	169.64 (18)
C2—C3—C4—C5	−48.9 (2)	C16—C11—C12—C13	−70.5 (2)
C15—C3—C4—C5	−168.94 (18)	C9—C8—C13—O4	170.37 (17)
C14—C3—C4—C5	71.6 (2)	C7—C8—C13—O4	−6.4 (3)
C3—C4—C5—O1	−159.53 (17)	C9—C8—C13—C12	−8.0 (3)
C3—C4—C5—C6	22.4 (3)	C7—C8—C13—C12	175.28 (17)
O2—C1—C6—C5	168.64 (17)	C11—C12—C13—O4	156.05 (18)
C2—C1—C6—C5	−11.4 (3)	C11—C12—C13—C8	−25.5 (3)
O2—C1—C6—C7	−8.7 (3)	C8—C7—C18—C19	−152.88 (17)
C2—C1—C6—C7	171.27 (17)	C6—C7—C18—C19	−17.1 (2)
O1—C5—C6—C1	−168.28 (18)	C8—C7—C18—C23	35.6 (2)
C4—C5—C6—C1	9.7 (3)	C6—C7—C18—C23	171.40 (16)
O1—C5—C6—C7	9.2 (3)	C23—C18—C19—C20	−0.6 (3)
C4—C5—C6—C7	−172.81 (17)	C7—C18—C19—C20	−172.40 (17)
C1—C6—C7—C8	83.6 (2)	C18—C19—C20—C21	1.1 (3)
C5—C6—C7—C8	−93.71 (19)	C19—C20—C21—O5	178.59 (17)
C1—C6—C7—C18	−51.6 (2)	C19—C20—C21—C22	−0.9 (3)
C5—C6—C7—C18	131.04 (17)	O5—C21—C22—C23	−179.26 (16)
C6—C7—C8—C13	90.6 (2)	C20—C21—C22—C23	0.3 (3)
C18—C7—C8—C13	−133.42 (17)	C21—C22—C23—C18	0.2 (3)
C6—C7—C8—C9	−86.00 (19)	C19—C18—C23—C22	0.0 (3)
C18—C7—C8—C9	50.0 (2)	C7—C18—C23—C22	171.99 (16)
C13—C8—C9—O3	−165.22 (17)	O5—C24—C25—C26	−67.1 (2)
C7—C8—C9—O3	11.5 (3)	C24—C25—C26—C27	−174.0 (2)
C13—C8—C9—C10	12.5 (3)	C20—C21—O5—C24	5.5 (3)
C7—C8—C9—C10	−170.83 (16)	C22—C21—O5—C24	−174.98 (17)
O3—C9—C10—C11	−165.42 (16)	C25—C24—O5—C21	174.82 (16)
C8—C9—C10—C11	16.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C18–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.92 (2)	1.66 (2)	2.566 (2)	166 (3)
O4—H4···O1	0.94 (3)	1.72 (3)	2.655 (2)	171 (3)
C10—H10B···Cg1ⁱ	0.97	3.11	3.773 (2)	127

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Dr P. K. Sudhadevi antharjanam and SAIF, IIT Madras for intensity data collection.

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