Crystal structure of (E)-1,3-bis­(6-methoxy­naphthalen-2-yl)prop-2-en-1-one

Patel, P.N.; Chadha, A.

doi:10.1107/S2056989015019714

organic compounds

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ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o884-o885

https://doi.org/10.1107/S2056989015019714

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Crystal structure of (E)-1,3-bis(6-methoxynaphthalen-2-yl)prop-2-en-1-one

Paresh N. Patel ^a and Anju Chadha ^b ^*

^aDepartment of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India, and ^bDepartment of Biotechnology and National Center for Catalysis Research, Indian Institute of Technology Madras, Chennai 600 036, India
^*Correspondence e-mail: anjuc@iitm.ac.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 24 September 2015; accepted 19 October 2015; online 24 October 2015)

In the title compound, C₂₅H₂₀O₃, the central –C(=O)—C=C– chain is disordered over two positions about the central C atom, with an occupancy ratio of 0.848 (6):0.152 (6). The molecule is twisted with the two naphthalene ring systems being inclined to one another by 52.91 (9)°. In the crystal, molecules are linked by C—H⋯π interactions, forming a three-dimensional structure. The structure was refined as a two-component twin with a 180 ° rotation about the c* axis.

Keywords: crystal structure; bis-naphthalene; chalcone; C—H⋯π interactions.

CCDC reference: 1432044

1. Related literature

For natural sources of chalcones and their derivatives, see: Anderson & Markham (2006 ); Yadav et al. (2011 ). For examples of their biological activities, see: Liu et al. (2011 ); Siddiqui et al. (2012 ). For their use as synthons for the preparation of five- and six-membered ring systems, see: Powers et al. (1998 ). For their use as intermediates in the synthesis of pharmaceutical molecules, see: Perozo-Rondon et al. (2006 ). For the crystal structure of a closely related compound, 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop-2-en-1-one, see: Yathirajan et al. (2006 ).

2. Experimental

2.1. Crystal data

C₂₅H₂₀O₃
M_r = 368.41
Monoclinic P 2₁ /c
a = 6.027 (5) Å
b = 19.926 (5) Å
c = 15.415 (5) Å
β = 90.366 (5)°
V = 1851.2 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS: Bruker, 2004 ) T_min = 0.932, T_max = 0.951
3345 measured reflections
3345 independent reflections
1837 reflections with I > 2σ(I)
R_int = 0.072

2.3. Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.179
S = 1.13
3345 reflections
267 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of rings C5-C10 and C17-C22, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg4ⁱ	0.93	2.86	3.543 (4)	131
C18—H18⋯Cg2ⁱⁱ	0.93	2.85	3.611 (4)	140
C23—H23⋯Cg2ⁱⁱⁱ	0.93	2.88	3.592 (4)	134
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1432044

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015019714/su5219sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019714/su5219Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019714/su5219Isup3.cml

checkCIF report

Comments top

Heteroaryl chalcones are well documented as important synthons for a number of pharmaceutically active molecules, and extensive investigations have demonstrated the biological properties of natural and synthetic chalcones. These properties are largely attributed to the presence of the a,ß-unsaturated ketone moiety in the chalcone (Anderson & Markham, 2006; Yadav et al., 2011). Chalcones are reported to possess many useful properties, for example antibacterial [Liu et al., 2011] and antifungal [Siddiqui et al., 2012]. These compounds are important synthons for the preparation of five- and six-membered ring systems [Powers et al., 1998] as well as intermediates in the synthesis of many pharmaceutically useful molecules [Perozo-Rondon et al., 2006]. Given such varied pharmacological activities and synthetic utilities, chalcones have always attracted chemists to develop newer molecules and study their biological activities. Adding to the list of active heteroaryl chalcones for use in pharmaceutical applications and as an effective synthon for the preparation of five- and six-member ring systems, we report herein on the synthesis and crystal structure of the title compound.

In the title compound, Fig. 1, the central -C12(═O2)—C13═C14- chain is disordered over two positions about the central atom C13 with an occupancy ratio of 0.848 (6):0.152 (6) for atom O2 (O2A:O2B). The molecule is twisted with the two naphthalene ring systems being inclined to one another by 52.91 (9)°. This situation is similar to that in compound 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop- 2-en-1-one (Yathirajan et al., 2006), where the two naphthalene ring systems are inclined to one another by 54.41 (3) °.

In the crystal, molecules are linked by C—H···π interactions forming a three-dimensional structure. There are no other intra- or inter-molecular interactions present.

Synthesis and crystallization top

To a stirred solution of 6-methoxy-2-naphthaldehyde (1.86 g, 10 mmol) in ethanol (10 ml), 1-(6-methoxynaphthalen-2-yl) ethanone (2.00 g, 10 mmol) dissolved in ethanol (10 ml) was added portion wise. The reaction mixture was stirred at room temperature for an additional 20 min, during which time it turned to a homogeneous solution. KOH solution (40%, 2 ml) was then added drop wise and the resultant mixture was stirred at room temperature for 2 h. The precipitated product was then collected by filtration and purified by recrystallization from chloroform–methanol (1:1 v/v, 10 ml), to afford 2.29 g (82%) of the title compound as yellow–brown needles (m.p.: 396-397 K). Colourless block-like crystals, suitable for X-ray diffraction, were obtained by crystallization from a 1 ml saturated solution in ethanol.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93-0.96 Å with U_iso(H) = 15.U_eq(C-methyl) and 1.2U_eq(C) for other H atoms. The central -C12(═O2)—C13═C14- chain is disordered over two positions about the central atom C13 with an occupancy ratio of 0.848 (6):0.152 (6) for atom O2 (O2A:O2B). The structure was refined as a two-component twin: 180 ° rotation about the c* axis; BASF = 0.063 (1).

Related literature top

For natural sources of chalcones and their derivatives, see: Anderson & Markham (2006); Yadav et al. (2011). For examples of their biological activities, see: Liu et al. (2011); Siddiqui et al. (2012). For their use as synthons for the preparation of five- and six-membered ring systems, see: Powers et al. (1998). For their use as intermediates in the synthesis of pharmaceutical molecules, see: Perozo-Rondon et al. (2006). For the crystal structure of a closely related compound, 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop-2-en-1-one, see: Yathirajan et al. (2006).

Structure description top

In the crystal, molecules are linked by C—H···π interactions forming a three-dimensional structure. There are no other intra- or inter-molecular interactions present.

For natural sources of chalcones and their derivatives, see: Anderson & Markham (2006); Yadav et al. (2011). For examples of their biological activities, see: Liu et al. (2011); Siddiqui et al. (2012). For their use as synthons for the preparation of five- and six-membered ring systems, see: Powers et al. (1998). For their use as intermediates in the synthesis of pharmaceutical molecules, see: Perozo-Rondon et al. (2006). For the crystal structure of a closely related compound, 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop-2-en-1-one, see: Yathirajan et al. (2006).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered O atom is shown.
	Fig. 2. A view along the c axis of the crystal packing of the title compound.

(E)-1,3-Bis(6-methoxynaphthalen-2-yl)prop-2-en-1-one top

Crystal data top

C₂₅H₂₀O₃	F(000) = 776
M_r = 368.41	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.027 (5) Å	Cell parameters from 4691 reflections
b = 19.926 (5) Å	θ = 2.6–22.4°
c = 15.415 (5) Å	µ = 0.09 mm⁻¹
β = 90.366 (5)°	T = 293 K
V = 1851.2 (17) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1837 reflections with I > 2σ(I)
Radiation source: Sealed tube	R_int = 0.072
ω and φ scan	θ_max = 25.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS: Bruker, 2004)	h = −7→7
T_min = 0.932, T_max = 0.951	k = −23→23
3345 measured reflections	l = 0→18
3345 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.061	w = 1/[σ²(F_o²) + (0.076P)² + 0.242P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.179	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.19 e Å⁻³
3345 reflections	Δρ_min = −0.16 e Å⁻³
267 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0042 (12)

Crystal data top

C₂₅H₂₀O₃	V = 1851.2 (17) Å³
M_r = 368.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.027 (5) Å	µ = 0.09 mm⁻¹
b = 19.926 (5) Å	T = 293 K
c = 15.415 (5) Å	0.30 × 0.20 × 0.20 mm
β = 90.366 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3345 independent reflections
Absorption correction: multi-scan (SADABS: Bruker, 2004)	1837 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.951	R_int = 0.072
3345 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	2 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.13	Δρ_max = 0.19 e Å⁻³
3345 reflections	Δρ_min = −0.16 e Å⁻³
267 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. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.7149 (4)	0.07041 (12)	0.81151 (15)	0.0752 (7)
O2A	0.3022 (4)	0.46629 (14)	0.8854 (2)	0.0831 (12)	0.848 (6)
O2B	0.3818 (18)	0.5689 (8)	0.9159 (10)	0.075 (6)	0.152 (6)
O3	1.0538 (4)	0.94015 (12)	0.91441 (16)	0.0810 (8)
C1	0.9200 (6)	0.05490 (18)	0.7708 (3)	0.0878 (12)
H1A	0.9265	0.0769	0.7155	0.132*
H1B	0.9311	0.0072	0.7628	0.132*
H1C	1.0405	0.0701	0.8068	0.132*
C2	0.6696 (5)	0.13625 (18)	0.82763 (19)	0.0588 (9)
C3	0.4657 (5)	0.14718 (18)	0.8680 (2)	0.0637 (9)
H3	0.3764	0.1108	0.8821	0.076*
C4	0.3971 (5)	0.20984 (18)	0.88679 (19)	0.0624 (9)
H4	0.2601	0.2161	0.9130	0.075*
C5	0.5308 (4)	0.26629 (16)	0.86723 (18)	0.0507 (8)
C6	0.4623 (5)	0.33174 (17)	0.88371 (18)	0.0582 (9)
H6	0.3225	0.3389	0.9071	0.070*
C7	0.5958 (5)	0.38617 (16)	0.86635 (19)	0.0568 (8)
C8	0.8060 (5)	0.37394 (18)	0.8290 (2)	0.0631 (9)
H8	0.9001	0.4098	0.8174	0.076*
C9	0.8711 (5)	0.31106 (18)	0.8100 (2)	0.0619 (9)
H9	1.0084	0.3045	0.7842	0.074*
C10	0.7380 (4)	0.25513 (16)	0.82814 (18)	0.0513 (8)
C11	0.8029 (5)	0.18913 (17)	0.80906 (19)	0.0576 (8)
H11	0.9397	0.1815	0.7833	0.069*
C12	0.5122 (6)	0.45453 (18)	0.8827 (2)	0.0683 (10)
H12B	0.3602	0.4619	0.8864	0.082*	0.152 (6)
C13	0.6636 (5)	0.51023 (18)	0.8930 (2)	0.0664 (9)
H13A	0.8128	0.5016	0.9039	0.080*
C14	0.5946 (5)	0.57381 (18)	0.8872 (2)	0.0660 (9)
H14A	0.4446	0.5796	0.8747	0.079*	0.848 (6)
C15	0.7225 (5)	0.63517 (17)	0.89786 (19)	0.0548 (8)
C16	0.6339 (5)	0.69511 (17)	0.87011 (19)	0.0575 (9)
H16	0.4948	0.6948	0.8436	0.069*
C17	0.7436 (4)	0.75620 (16)	0.87992 (18)	0.0514 (8)
C18	0.6536 (5)	0.81769 (19)	0.8512 (2)	0.0628 (9)
H18	0.5163	0.8177	0.8234	0.075*
C19	0.7603 (5)	0.87635 (18)	0.8629 (2)	0.0656 (9)
H19	0.6986	0.9161	0.8423	0.079*
C20	0.9658 (5)	0.87709 (17)	0.9066 (2)	0.0613 (9)
C21	1.0620 (5)	0.81927 (16)	0.93433 (18)	0.0534 (8)
H21	1.1999	0.8206	0.9617	0.064*
C22	0.9538 (4)	0.75732 (16)	0.92185 (17)	0.0491 (7)
C23	1.0433 (5)	0.69571 (16)	0.94924 (19)	0.0536 (8)
H23	1.1821	0.6953	0.9759	0.064*
C24	0.9338 (5)	0.63677 (16)	0.93804 (19)	0.0573 (8)
H24	0.9986	0.5970	0.9570	0.069*
C25	1.2506 (6)	0.94859 (18)	0.9618 (3)	0.0897 (12)
H25A	1.2274	0.9351	1.0209	0.135*
H25B	1.2941	0.9949	0.9603	0.135*
H25C	1.3654	0.9215	0.9368	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0769 (16)	0.0723 (18)	0.0765 (16)	−0.0081 (12)	0.0102 (13)	0.0067 (13)
O2A	0.0531 (19)	0.084 (2)	0.112 (2)	−0.0078 (14)	0.0012 (15)	0.0059 (17)
O2B	0.039 (9)	0.096 (13)	0.091 (12)	0.008 (7)	−0.008 (7)	−0.015 (9)
O3	0.0854 (17)	0.0663 (17)	0.0910 (18)	−0.0005 (13)	−0.0171 (14)	0.0050 (13)
C1	0.081 (3)	0.089 (3)	0.093 (3)	0.006 (2)	0.014 (2)	0.006 (2)
C2	0.055 (2)	0.071 (2)	0.0501 (19)	−0.0080 (17)	−0.0043 (15)	0.0090 (17)
C3	0.057 (2)	0.073 (3)	0.061 (2)	−0.0186 (18)	0.0040 (16)	0.0117 (19)
C4	0.0439 (17)	0.092 (3)	0.052 (2)	−0.0166 (18)	0.0061 (14)	0.0073 (19)
C5	0.0416 (16)	0.071 (2)	0.0393 (16)	−0.0106 (15)	−0.0027 (13)	0.0049 (16)
C6	0.0461 (18)	0.088 (3)	0.0403 (17)	−0.0165 (17)	−0.0003 (13)	−0.0003 (17)
C7	0.0517 (19)	0.069 (2)	0.0495 (19)	−0.0129 (16)	−0.0015 (14)	−0.0002 (16)
C8	0.056 (2)	0.072 (3)	0.061 (2)	−0.0228 (17)	0.0017 (16)	0.0061 (18)
C9	0.0464 (18)	0.084 (3)	0.056 (2)	−0.0174 (17)	0.0040 (15)	0.0064 (19)
C10	0.0419 (16)	0.072 (2)	0.0400 (16)	−0.0126 (16)	−0.0033 (13)	0.0063 (16)
C11	0.0439 (17)	0.079 (2)	0.0501 (19)	−0.0083 (17)	0.0025 (14)	0.0114 (17)
C12	0.070 (2)	0.082 (3)	0.053 (2)	−0.021 (2)	0.0053 (17)	0.0013 (18)
C13	0.058 (2)	0.075 (3)	0.066 (2)	−0.0085 (19)	−0.0023 (16)	0.0023 (19)
C14	0.0477 (19)	0.082 (3)	0.069 (2)	−0.0019 (18)	−0.0021 (16)	−0.014 (2)
C15	0.0490 (18)	0.068 (2)	0.0475 (18)	0.0004 (16)	−0.0006 (14)	−0.0124 (16)
C16	0.0439 (17)	0.077 (3)	0.0512 (19)	0.0023 (16)	−0.0057 (14)	−0.0156 (17)
C17	0.0464 (17)	0.065 (2)	0.0428 (17)	0.0082 (16)	−0.0002 (14)	−0.0077 (15)
C18	0.0486 (18)	0.086 (3)	0.053 (2)	0.0098 (18)	−0.0033 (15)	−0.0082 (19)
C19	0.063 (2)	0.071 (3)	0.063 (2)	0.0156 (18)	−0.0007 (17)	0.0020 (18)
C20	0.063 (2)	0.064 (2)	0.057 (2)	0.0004 (18)	0.0026 (16)	−0.0042 (17)
C21	0.0472 (17)	0.066 (2)	0.0469 (18)	0.0018 (16)	−0.0007 (14)	0.0005 (16)
C22	0.0457 (16)	0.063 (2)	0.0389 (16)	0.0029 (15)	0.0028 (13)	−0.0048 (15)
C23	0.0441 (17)	0.070 (2)	0.0469 (18)	0.0016 (16)	−0.0069 (13)	−0.0036 (16)
C24	0.0536 (19)	0.066 (2)	0.0521 (19)	0.0056 (16)	−0.0011 (15)	−0.0022 (16)
C25	0.081 (3)	0.076 (3)	0.112 (3)	−0.006 (2)	−0.013 (2)	0.000 (2)

Geometric parameters (Å, º) top

O1—C2	1.363 (4)	C12—C13	1.445 (4)
O1—C1	1.423 (4)	C12—H12B	0.9300
O2A—C12	1.288 (4)	C13—C14	1.336 (4)
O2B—C14	1.363 (11)	C13—H13A	0.9300
O3—C20	1.369 (4)	C14—C15	1.454 (4)
O3—C25	1.400 (4)	C14—H14A	0.9300
C1—H1A	0.9600	C15—C16	1.375 (4)
C1—H1B	0.9600	C15—C24	1.413 (4)
C1—H1C	0.9600	C16—C17	1.393 (4)
C2—C11	1.357 (4)	C16—H16	0.9300
C2—C3	1.398 (4)	C17—C18	1.410 (4)
C3—C4	1.347 (4)	C17—C22	1.419 (4)
C3—H3	0.9300	C18—C19	1.346 (4)
C4—C5	1.417 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.406 (5)
C5—C6	1.392 (4)	C19—H19	0.9300
C5—C10	1.408 (4)	C20—C21	1.358 (4)
C6—C7	1.377 (4)	C21—C22	1.409 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.416 (4)	C22—C23	1.405 (4)
C7—C12	1.475 (4)	C23—C24	1.358 (4)
C8—C9	1.346 (4)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.402 (4)	C25—H25A	0.9600
C9—H9	0.9300	C25—H25B	0.9600
C10—C11	1.404 (4)	C25—H25C	0.9600
C11—H11	0.9300

C2—O1—C1	117.7 (3)	C14—C13—H13A	119.2
C20—O3—C25	118.9 (3)	C12—C13—H13A	119.2
O1—C1—H1A	109.5	C13—C14—O2B	101.7 (7)
O1—C1—H1B	109.5	C13—C14—C15	128.7 (3)
H1A—C1—H1B	109.5	O2B—C14—C15	121.5 (7)
O1—C1—H1C	109.5	C13—C14—H14A	115.6
H1A—C1—H1C	109.5	C15—C14—H14A	115.6
H1B—C1—H1C	109.5	C16—C15—C24	117.6 (3)
C11—C2—O1	126.1 (3)	C16—C15—C14	119.4 (3)
C11—C2—C3	119.8 (3)	C24—C15—C14	123.0 (3)
O1—C2—C3	114.1 (3)	C15—C16—C17	122.8 (3)
C4—C3—C2	120.8 (3)	C15—C16—H16	118.6
C4—C3—H3	119.6	C17—C16—H16	118.6
C2—C3—H3	119.6	C16—C17—C18	123.0 (3)
C3—C4—C5	120.9 (3)	C16—C17—C22	119.0 (3)
C3—C4—H4	119.5	C18—C17—C22	118.0 (3)
C5—C4—H4	119.5	C19—C18—C17	122.0 (3)
C6—C5—C10	119.4 (3)	C19—C18—H18	119.0
C6—C5—C4	122.4 (3)	C17—C18—H18	119.0
C10—C5—C4	118.2 (3)	C18—C19—C20	119.5 (3)
C7—C6—C5	121.9 (3)	C18—C19—H19	120.3
C7—C6—H6	119.1	C20—C19—H19	120.3
C5—C6—H6	119.1	C21—C20—O3	125.9 (3)
C6—C7—C8	117.9 (3)	C21—C20—C19	121.0 (3)
C6—C7—C12	119.6 (3)	O3—C20—C19	113.1 (3)
C8—C7—C12	122.4 (3)	C20—C21—C22	120.3 (3)
C9—C8—C7	120.8 (3)	C20—C21—H21	119.9
C9—C8—H8	119.6	C22—C21—H21	119.9
C7—C8—H8	119.6	C23—C22—C21	123.2 (3)
C8—C9—C10	121.9 (3)	C23—C22—C17	117.6 (3)
C8—C9—H9	119.0	C21—C22—C17	119.2 (3)
C10—C9—H9	119.0	C24—C23—C22	122.2 (3)
C9—C10—C11	122.8 (3)	C24—C23—H23	118.9
C9—C10—C5	118.0 (3)	C22—C23—H23	118.9
C11—C10—C5	119.1 (3)	C23—C24—C15	120.7 (3)
C2—C11—C10	121.1 (3)	C23—C24—H24	119.6
C2—C11—H11	119.4	C15—C24—H24	119.6
C10—C11—H11	119.4	O3—C25—H25A	109.5
O2A—C12—C13	118.5 (3)	O3—C25—H25B	109.5
O2A—C12—C7	120.7 (3)	H25A—C25—H25B	109.5
C13—C12—C7	120.8 (3)	O3—C25—H25C	109.5
C13—C12—H12B	119.6	H25A—C25—H25C	109.5
C7—C12—H12B	119.6	H25B—C25—H25C	109.5
C14—C13—C12	121.7 (3)

C1—O1—C2—C11	−0.5 (5)	C12—C13—C14—O2B	30.1 (7)
C1—O1—C2—C3	−179.7 (3)	C12—C13—C14—C15	178.3 (3)
C11—C2—C3—C4	1.7 (5)	C13—C14—C15—C16	165.1 (3)
O1—C2—C3—C4	−179.0 (3)	O2B—C14—C15—C16	−52.0 (9)
C2—C3—C4—C5	−0.9 (5)	C13—C14—C15—C24	−16.7 (5)
C3—C4—C5—C6	178.3 (3)	O2B—C14—C15—C24	126.2 (8)
C3—C4—C5—C10	−0.4 (4)	C24—C15—C16—C17	0.1 (4)
C10—C5—C6—C7	−2.9 (4)	C14—C15—C16—C17	178.4 (3)
C4—C5—C6—C7	178.4 (3)	C15—C16—C17—C18	179.7 (3)
C5—C6—C7—C8	1.4 (4)	C15—C16—C17—C22	−1.3 (4)
C5—C6—C7—C12	178.2 (3)	C16—C17—C18—C19	178.6 (3)
C6—C7—C8—C9	0.9 (5)	C22—C17—C18—C19	−0.3 (4)
C12—C7—C8—C9	−175.8 (3)	C17—C18—C19—C20	−1.3 (5)
C7—C8—C9—C10	−1.6 (5)	C25—O3—C20—C21	−6.3 (5)
C8—C9—C10—C11	−179.9 (3)	C25—O3—C20—C19	175.6 (3)
C8—C9—C10—C5	0.0 (4)	C18—C19—C20—C21	2.4 (5)
C6—C5—C10—C9	2.2 (4)	C18—C19—C20—O3	−179.4 (3)
C4—C5—C10—C9	−179.1 (3)	O3—C20—C21—C22	−179.7 (3)
C6—C5—C10—C11	−177.9 (3)	C19—C20—C21—C22	−1.8 (5)
C4—C5—C10—C11	0.8 (4)	C20—C21—C22—C23	−179.7 (3)
O1—C2—C11—C10	179.5 (3)	C20—C21—C22—C17	0.1 (4)
C3—C2—C11—C10	−1.3 (4)	C16—C17—C22—C23	1.8 (4)
C9—C10—C11—C2	179.9 (3)	C18—C17—C22—C23	−179.2 (3)
C5—C10—C11—C2	0.0 (4)	C16—C17—C22—C21	−178.0 (3)
C6—C7—C12—O2A	−22.7 (5)	C18—C17—C22—C21	1.0 (4)
C8—C7—C12—O2A	154.0 (3)	C21—C22—C23—C24	178.7 (3)
C6—C7—C12—C13	159.5 (3)	C17—C22—C23—C24	−1.2 (4)
C8—C7—C12—C13	−23.8 (5)	C22—C23—C24—C15	0.0 (4)
O2A—C12—C13—C14	−14.0 (5)	C16—C15—C24—C23	0.6 (4)
C7—C12—C13—C14	163.8 (3)	C14—C15—C24—C23	−177.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of rings C5-C10 and C17-C22, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg4ⁱ	0.93	2.86	3.543 (4)	131
C18—H18···Cg2ⁱⁱ	0.93	2.85	3.611 (4)	140
C23—H23···Cg2ⁱⁱⁱ	0.93	2.88	3.592 (4)	134

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of rings C5-C10 and C17-C22, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg4ⁱ	0.93	2.86	3.543 (4)	131
C18—H18···Cg2ⁱⁱ	0.93	2.85	3.611 (4)	140
C23—H23···Cg2ⁱⁱⁱ	0.93	2.88	3.592 (4)	134

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

Acknowledgements

PNP is thankful to the Indian Institute of Technology, Madras, for an Institute postdoctoral fellowship. The authors thank SAIF, IIT Madras, for the spectral analysis.

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Volume 71| Part 11| November 2015| Pages o884-o885

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