organic compounds
E)-1,3-bis(6-methoxynaphthalen-2-yl)prop-2-en-1-one
of (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
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 ); 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 of a closely related compound, 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop-2-en-1-one, see: Yathirajan et al. (2006).
and their derivatives, see: Anderson & Markham (20062. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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
https://doi.org/10.1107/S2056989015019714/su5219sup1.cif
contains datablocks global, I. DOI: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
Heteroaryl
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 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). 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, have always attracted chemists to develop newer molecules and study their biological activities. Adding to the list of active heteroaryl 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 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.
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
in ethanol.Crystal data, data collection and structure ═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).
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 Uiso(H) = 15.Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. The central -C12(Heteroaryl
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 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). 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, have always attracted chemists to develop newer molecules and study their biological activities. Adding to the list of active heteroaryl 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 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.
For natural sources of
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 of a closely related compound, 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop-2-en-1-one, see: Yathirajan et al. (2006).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
in ethanol. detailsCrystal data, data collection and structure ═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).
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 Uiso(H) = 15.Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. The central -C12(Data collection: APEX2 (Bruker, 2004); cell
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).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. |
C25H20O3 | F(000) = 776 |
Mr = 368.41 | Dx = 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 |
Bruker Kappa APEXII CCD diffractometer | 1837 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.072 |
ω and φ scan | θmax = 25.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS: Bruker, 2004) | h = −7→7 |
Tmin = 0.932, Tmax = 0.951 | k = −23→23 |
3345 measured reflections | l = 0→18 |
3345 independent reflections |
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(Fo2) + (0.076P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.179 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.19 e Å−3 |
3345 reflections | Δρmin = −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) |
C25H20O3 | V = 1851.2 (17) Å3 |
Mr = 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)° |
Bruker Kappa APEXII CCD diffractometer | 3345 independent reflections |
Absorption correction: multi-scan (SADABS: Bruker, 2004) | 1837 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.951 | Rint = 0.072 |
3345 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 2 restraints |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.19 e Å−3 |
3345 reflections | Δρmin = −0.16 e Å−3 |
267 parameters |
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. |
x | y | z | Uiso*/Ueq | 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* |
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) |
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) |
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. |
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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