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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2015 Jan 1;71(Pt 1):16–18. doi: 10.1107/S2056989014025390

Crystal structure of 5-(4-benzyl­oxyphen­yl)-3-(4-meth­oxy­phen­yl)-6-methyl­cyclo­hex-2-en-1-one

S Sathya a, D Reuben Jonathan b, J Sidharthan c, R Vasanthi a, G Usha a,*
PMCID: PMC4331857  PMID: 25705439

5-(4-Benzyl­oxyphen­yl)-3-(4-meth­oxy­phen­yl)-6-methyl­cyclo­hex-2-en-1-one crystallized with two independent mol­ecules in the asymmetric unit. The cyclo­hexene ring adopts an envelope conformation in both mol­ecules, with the C atom to which is attached the central benzene ring as the flap. The crystal packing, is stabilized by C—H⋯π inter­actions.

Keywords: crystal structure, cyclo­hexene, cyclcohexen-1-one

Abstract

The title compound, C27H26O3, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule A, the plane of the central benzene ring forms dihedral angles of 75.78 (14) and 52.75 (16)° with that of the terminal benzene rings, and the dihedral angle between the planes of the terminal benzene rings is 51.49 (17)°. The corresponding values for mol­ecule B are 75.18 (14), 58.11 (16) and 47.91 (16)°, respectively. The cyclo­hexene ring adopts an envelope conformation in both mol­ecules, with the C atom to which is attached the central benzene ring as the flap. The crystal packing, is stabilized by C—H⋯π inter­actions.

Structural commentary  

Cyclo­hexenone is a versatile inter­mediate used in the synthesis of a variety of chemical products such as pharmaceuticals and fragrances. Cyclo­hexenone and cyclo­hexenone derivatives are known for anti-inflammatory and analgesic activities (Kalluraya & Rahiman, 2003 ▸). α,β-Unsaturated carbonyl compounds have shown various biological activities such as anti­oxidant (Suksamrarn et al., 2003 ▸), anti­tumor (Kumar et al., 2003 ▸), anti­cancer (Modzelewska et al., 2006 ▸) and anti­malarial (Ferrer et al., 2009 ▸). In addition, chalcones are widely used in cosmetic compositions (Forestier et al., 1989 ▸; Podraze, 1991 ▸) and in applications of dyes (Asiri, 2003 ▸). Cyclo­hexenone derivatives are well known lead mol­ecules for the treatment of inflammation and autoimmune diseases (Tanaka et al., 1997 ▸). Apart from being biologically important compounds, chalcone derivatives show nonlinear optical (NLO) properties with excellent blue light transmittance and good crystallizability (Shettigar et al., 2006 ▸). In this context, herein we report the synthesis and crystal structure of the title compound.graphic file with name e-71-00016-scheme1.jpg

The title compound crystallized with two mol­ecules (A and B) in the asymmetric unit (Fig. 1 ▸). The benzyl­oxyphenyl and the meth­oxy­phenyl rings are linked with a cyclo­hexene ring. The C25—O1 and C25A—O1A bond lengths of 1.228 (3) and 1.224 (3) Å, respectively, indicate double-bond character. In both mol­ecules, the C—O bond lengths are in the range 1.362 (3)–1.414 (4) Å and represent single-bond character. In mol­ecule A, the torsion angles C5—C4—C7—C8 = 69.2 (4)° and C24—C9—C10—C11 = −16.0 (4)° show that the benzyl­oxyphenyl and meth­oxy­phenyl groups have a +sc and -sp orientation with respect to the cyclo­hexene moiety. The arrangement in mol­ecule B is slightly different, with torsion angles C5A—C4A—C7A—C8A = 111.5 (3)° and C24A—C9A—C10A—C11A = 20.8 (4)°. The cyclo­hexene ring in both mol­ecules adopts an envelope conformation with atoms C7 and C7A as the flaps in mol­ecules A and B, respectively.

Figure 1.

Figure 1

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The mol­ecular structure of the two independent mol­ecules of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

The crystal packing (Fig. 2 ▸) is stabilized by C—H⋯π inter­actions (Table 1 ▸).

Figure 2.

Figure 2

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A view along the b axis of the crystal packing of the title compound.

Table 1. Hydrogen-bond geometry (, ).

Cg3 and Cg8 are the centroids of rings C10-C15 and C10A-C15A, respectively.

DHA DH HA D A DHA
C2AH2A Cg3i 0.93 2.87 3.707(3) 150
C16AH16E Cg8ii 0.96 2.92 3.866(5) 168
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Synthesis and crystallization  

(2E)-3-(4-Benzyl­oxyphen­yl)-1-(4-meth­oxy­phen­yl)prop-2-en-1-one was synthesized following the literature procedure of Ezhilarasi et al. (2014 ▸). The synthesis of the title compound was carried out by following the reported procedure of Fun et al. (2012 ▸). In a 100 ml round-bottomeded flask, (2E)-3-(4-benzyl­oxyphen­yl)-1-(4-meth­oxy­phen­yl)prop-2-en-1-one (0.01 mol) and ethyl methyl ketone (0.01 mol) were refluxed in absolute alcohol (50 ml) in the presence of 10% sodium hydroxide solution (10 ml) for 1 h in an oil bath. The reaction mixture was then cooled and the precipitate obtained filtered, washed with distilled water and dried. The crude product was recrystallized twice from absolute alcohol (yield 80%), giving yellow block-like crystals.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The H atoms were positioned geometrically and treated as riding atoms, with C—H = 0.93–0.98 Å, and with U iso(H) = 1.5U eq(C) for methyl H atoms and 1.2U eq(C) for other H atoms.

Table 2. Experimental details.

Crystal data
Chemical formula C27H26O3
M r 398.48
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c () 20.5663(12), 15.2878(9), 14.5689(8)
() 107.938(4)
V (3) 4358.0(4)
Z 8
Radiation type Mo K
(mm1) 0.08
Crystal size (mm) 0.25 0.23 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2008 ▸)
T min, T max 0.981, 0.985
No. of measured, independent and observed [I > 2(I)] reflections 33189, 7901, 3714
R int 0.057
(sin /)max (1) 0.600
 
Refinement
R[F 2 > 2(F 2)], wR(F 2), S 0.063, 0.193, 0.99
No. of reflections 7901
No. of parameters 546
H-atom treatment H-atom parameters constrained
max, min (e 3) 0.31, 0.21
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Computer programs: APEX2 and SAINT (Bruker, 2008 ▸), SHELXS97 and SHELXL2014 (Sheldrick, 2008 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸), and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014025390/su5016sup1.cif

e-71-00016-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025390/su5016Isup2.hkl

e-71-00016-Isup2.hkl (432.8KB, hkl)
Click here for additional data file. (8.2KB, cml)

Supporting information file. DOI: 10.1107/S2056989014025390/su5016Isup3.cml

CCDC reference: 1035112

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection facilities.

supplementary crystallographic information

Crystal data

C27H26O3 F(000) = 1696
Mr = 398.48 Dx = 1.215 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
a = 20.5663 (12) Å Cell parameters from 10904 reflections
b = 15.2878 (9) Å θ = 1.0–28.4°
c = 14.5689 (8) Å µ = 0.08 mm−1
β = 107.938 (4)° T = 293 K
V = 4358.0 (4) Å3 Block, yellow
Z = 8 0.25 × 0.23 × 0.20 mm
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Data collection

Bruker Kappa APEXII CCD diffractometer 7901 independent reflections
Radiation source: fine-focus sealed tube 3714 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.057
ω and φ scan θmax = 25.3°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008) h = −24→24
Tmin = 0.981, Tmax = 0.985 k = −18→14
33189 measured reflections l = −17→17
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Refinement

Refinement on F2 Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.063 w = 1/[σ2(Fo2) + (0.1028P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.193 (Δ/σ)max < 0.001
S = 0.99 Δρmax = 0.31 e Å−3
7901 reflections Δρmin = −0.21 e Å−3
546 parameters Extinction correction: SHELXL2014 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints Extinction coefficient: 0.0020 (5)
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Special details

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

x y z Uiso*/Ueq
O1 0.16345 (12) 0.76886 (14) −0.02540 (14) 0.0871 (7)
O2 0.09475 (10) 1.08899 (13) 0.43402 (13) 0.0703 (6)
O3 0.19511 (12) 0.32014 (14) 0.35402 (16) 0.0890 (7)
C1 0.09377 (16) 1.02145 (18) 0.37052 (19) 0.0568 (7)
C2 0.03609 (16) 0.9860 (2) 0.3070 (2) 0.0666 (8)
H2 −0.0069 1.0070 0.3045 0.080*
C3 0.04228 (17) 0.91803 (19) 0.2459 (2) 0.0685 (8)
H3 0.0030 0.8946 0.2026 0.082*
C4 0.10415 (17) 0.88533 (19) 0.24821 (19) 0.0611 (8)
C5 0.16111 (17) 0.9217 (2) 0.3127 (2) 0.0725 (9)
H5 0.2039 0.9000 0.3156 0.087*
C6 0.15690 (17) 0.9899 (2) 0.3739 (2) 0.0680 (8)
H6 0.1963 1.0138 0.4165 0.082*
C7 0.11115 (18) 0.81052 (19) 0.18306 (19) 0.0728 (9)
H7 0.0646 0.7984 0.1416 0.087*
C8 0.13470 (14) 0.72774 (17) 0.23821 (17) 0.0540 (7)
H8A 0.1003 0.7096 0.2673 0.065*
H8B 0.1763 0.7400 0.2901 0.065*
C9 0.14816 (13) 0.65290 (17) 0.17931 (16) 0.0468 (7)
C10 0.15636 (12) 0.56499 (17) 0.22096 (17) 0.0471 (7)
C11 0.15574 (14) 0.48994 (19) 0.16688 (19) 0.0598 (8)
H11 0.1469 0.4953 0.1006 0.072*
C12 0.16766 (15) 0.4084 (2) 0.2074 (2) 0.0664 (8)
H12 0.1670 0.3599 0.1687 0.080*
C13 0.18067 (14) 0.39773 (19) 0.3056 (2) 0.0603 (8)
C14 0.17958 (16) 0.4705 (2) 0.3607 (2) 0.0687 (9)
H14 0.1870 0.4641 0.4266 0.082*
C15 0.16775 (15) 0.55200 (19) 0.32023 (19) 0.0602 (8)
H15 0.1672 0.5999 0.3593 0.072*
C16 0.2115 (3) 0.2467 (2) 0.3082 (3) 0.1329 (17)
H16A 0.2251 0.1997 0.3538 0.199*
H16B 0.2484 0.2609 0.2834 0.199*
H16C 0.1723 0.2293 0.2561 0.199*
C17 0.03159 (16) 1.1250 (2) 0.4337 (2) 0.0766 (9)
H17A 0.0054 1.0821 0.4564 0.092*
H17B 0.0054 1.1422 0.3688 0.092*
C18 0.04583 (16) 1.2034 (2) 0.4992 (2) 0.0624 (8)
C19 0.01360 (17) 1.2129 (2) 0.5687 (2) 0.0813 (10)
H19 −0.0156 1.1695 0.5775 0.098*
C20 0.0249 (2) 1.2872 (3) 0.6252 (3) 0.1090 (13)
H20 0.0027 1.2936 0.6716 0.131*
C21 0.0673 (2) 1.3505 (3) 0.6144 (3) 0.1217 (16)
H21 0.0743 1.4004 0.6528 0.146*
C22 0.0995 (2) 1.3410 (2) 0.5475 (3) 0.1185 (15)
H22 0.1292 1.3844 0.5400 0.142*
C23 0.08895 (19) 1.2682 (2) 0.4904 (3) 0.0904 (11)
H23 0.1117 1.2627 0.4445 0.108*
C24 0.15546 (14) 0.66994 (19) 0.09195 (18) 0.0576 (8)
H24 0.1613 0.6230 0.0547 0.069*
C25 0.15466 (15) 0.7571 (2) 0.05331 (19) 0.0642 (8)
C26 0.1498 (2) 0.8335 (2) 0.1167 (2) 0.0865 (11)
H26 0.1968 0.8428 0.1585 0.104*
C27 0.1309 (2) 0.9172 (2) 0.0609 (3) 0.1127 (14)
H27A 0.1608 0.9264 0.0226 0.169*
H27B 0.1351 0.9651 0.1050 0.169*
H27C 0.0845 0.9136 0.0195 0.169*
O1A 0.31086 (10) 0.78628 (13) 0.34094 (12) 0.0725 (6)
O2A 0.41660 (10) 1.09227 (13) 0.87045 (14) 0.0687 (6)
O3A 0.31787 (13) 0.31427 (14) 0.67545 (16) 0.0924 (8)
C1A 0.41218 (15) 1.02388 (17) 0.80701 (18) 0.0520 (7)
C2A 0.34719 (15) 0.99367 (19) 0.7637 (2) 0.0640 (8)
H2A 0.3105 1.0188 0.7786 0.077*
C3A 0.33616 (15) 0.9262 (2) 0.6981 (2) 0.0671 (8)
H3A 0.2920 0.9055 0.6701 0.080*
C4A 0.38969 (15) 0.88854 (17) 0.67276 (18) 0.0536 (7)
C5A 0.45373 (15) 0.91928 (18) 0.71752 (19) 0.0581 (8)
H5A 0.4905 0.8946 0.7023 0.070*
C6A 0.46610 (15) 0.98615 (19) 0.78505 (19) 0.0610 (8)
H6A 0.5105 1.0052 0.8152 0.073*
C7A 0.37676 (15) 0.81644 (18) 0.59723 (18) 0.0614 (8)
H7A 0.4214 0.8040 0.5892 0.074*
C8A 0.35410 (14) 0.73180 (17) 0.63033 (17) 0.0563 (7)
H8A1 0.3895 0.7118 0.6873 0.068*
H8A2 0.3133 0.7427 0.6487 0.068*
C9A 0.33916 (13) 0.66057 (17) 0.55616 (17) 0.0502 (7)
C10A 0.33737 (13) 0.56976 (18) 0.58785 (17) 0.0501 (7)
C11A 0.34401 (14) 0.4993 (2) 0.53198 (18) 0.0612 (8)
H11A 0.3521 0.5102 0.4736 0.073*
C12A 0.33929 (15) 0.4141 (2) 0.5583 (2) 0.0653 (8)
H12A 0.3453 0.3687 0.5192 0.078*
C13A 0.32555 (15) 0.39603 (19) 0.6431 (2) 0.0637 (8)
C14A 0.31987 (18) 0.4637 (2) 0.7010 (2) 0.0805 (10)
H14A 0.3116 0.4518 0.7590 0.097*
C15A 0.32618 (15) 0.5493 (2) 0.67559 (19) 0.0678 (9)
H15A 0.3230 0.5941 0.7171 0.081*
C16A 0.3163 (2) 0.2418 (2) 0.6145 (3) 0.1197 (15)
H16D 0.3133 0.1888 0.6482 0.180*
H16E 0.3572 0.2410 0.5960 0.180*
H16F 0.2772 0.2465 0.5579 0.180*
C17A 0.48132 (16) 1.1279 (2) 0.9177 (2) 0.0749 (9)
H17C 0.5054 1.1398 0.8713 0.090*
H17D 0.5082 1.0866 0.9648 0.090*
C18A 0.47207 (14) 1.21032 (18) 0.9665 (2) 0.0574 (8)
C19A 0.50644 (16) 1.2251 (2) 1.0626 (2) 0.0757 (9)
H19A 0.5340 1.1816 1.0994 0.091*
C20A 0.5000 (2) 1.3042 (3) 1.1042 (2) 0.0982 (12)
H20A 0.5234 1.3133 1.1691 0.118*
C21A 0.4603 (2) 1.3691 (3) 1.0527 (3) 0.0980 (12)
H21A 0.4567 1.4224 1.0815 0.118*
C22A 0.42632 (18) 1.3549 (2) 0.9592 (3) 0.0905 (11)
H22A 0.3984 1.3987 0.9234 0.109*
C23A 0.43207 (16) 1.2772 (2) 0.9156 (2) 0.0741 (9)
H23A 0.4085 1.2695 0.8505 0.089*
C24A 0.32630 (14) 0.68225 (18) 0.46206 (18) 0.0550 (7)
H24A 0.3189 0.6372 0.4171 0.066*
C25A 0.32344 (14) 0.77137 (19) 0.42723 (18) 0.0560 (7)
C26A 0.33199 (16) 0.84476 (18) 0.49948 (18) 0.0660 (8)
H26A 0.2866 0.8546 0.5062 0.079*
C27A 0.35178 (17) 0.92969 (18) 0.4628 (2) 0.0783 (10)
H27D 0.3242 0.9385 0.3971 0.117*
H27E 0.3991 0.9276 0.4662 0.117*
H27F 0.3446 0.9771 0.5018 0.117*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.137 (2) 0.0897 (17) 0.0539 (12) 0.0068 (13) 0.0580 (13) 0.0091 (11)
O2 0.0811 (15) 0.0689 (14) 0.0623 (12) 0.0179 (11) 0.0242 (10) −0.0115 (11)
O3 0.142 (2) 0.0552 (15) 0.0934 (16) 0.0115 (13) 0.0706 (15) 0.0121 (13)
C1 0.078 (2) 0.0490 (19) 0.0469 (16) 0.0108 (16) 0.0249 (15) 0.0037 (15)
C2 0.077 (2) 0.064 (2) 0.0652 (19) 0.0079 (17) 0.0317 (17) −0.0022 (17)
C3 0.085 (2) 0.063 (2) 0.0616 (18) 0.0008 (17) 0.0284 (16) −0.0073 (17)
C4 0.089 (2) 0.0539 (19) 0.0407 (15) 0.0054 (18) 0.0209 (16) 0.0042 (14)
C5 0.090 (2) 0.069 (2) 0.0664 (19) 0.0242 (18) 0.0344 (18) 0.0026 (18)
C6 0.083 (2) 0.066 (2) 0.0554 (17) 0.0114 (18) 0.0213 (16) −0.0032 (16)
C7 0.120 (3) 0.061 (2) 0.0453 (16) 0.0132 (18) 0.0367 (17) 0.0002 (15)
C8 0.0754 (19) 0.0525 (19) 0.0412 (14) −0.0031 (14) 0.0284 (13) −0.0042 (14)
C9 0.0563 (17) 0.0478 (18) 0.0386 (13) −0.0010 (13) 0.0182 (12) −0.0064 (13)
C10 0.0566 (17) 0.0483 (18) 0.0419 (13) −0.0023 (13) 0.0231 (12) −0.0076 (14)
C11 0.078 (2) 0.058 (2) 0.0452 (15) −0.0028 (16) 0.0214 (14) −0.0085 (16)
C12 0.085 (2) 0.057 (2) 0.0624 (18) −0.0053 (16) 0.0308 (16) −0.0175 (17)
C13 0.081 (2) 0.0457 (19) 0.0661 (18) −0.0003 (15) 0.0404 (16) 0.0031 (17)
C14 0.108 (3) 0.059 (2) 0.0527 (17) 0.0027 (17) 0.0448 (17) −0.0004 (17)
C15 0.091 (2) 0.0497 (19) 0.0504 (16) 0.0001 (15) 0.0378 (15) −0.0039 (15)
C16 0.231 (5) 0.065 (3) 0.123 (3) 0.039 (3) 0.084 (3) 0.007 (3)
C17 0.082 (2) 0.074 (2) 0.077 (2) 0.0138 (18) 0.0280 (17) −0.0069 (18)
C18 0.081 (2) 0.058 (2) 0.0554 (17) 0.0123 (17) 0.0311 (15) 0.0003 (16)
C19 0.099 (3) 0.086 (3) 0.072 (2) −0.008 (2) 0.0455 (19) −0.002 (2)
C20 0.136 (4) 0.126 (4) 0.094 (3) −0.013 (3) 0.078 (3) −0.041 (3)
C21 0.169 (4) 0.085 (3) 0.143 (4) −0.024 (3) 0.096 (4) −0.049 (3)
C22 0.182 (4) 0.064 (3) 0.150 (4) −0.022 (3) 0.109 (3) −0.027 (3)
C23 0.133 (3) 0.071 (3) 0.096 (3) −0.004 (2) 0.079 (2) −0.005 (2)
C24 0.077 (2) 0.060 (2) 0.0412 (14) 0.0015 (15) 0.0271 (13) −0.0041 (14)
C25 0.087 (2) 0.069 (2) 0.0443 (15) 0.0024 (16) 0.0328 (15) 0.0007 (16)
C26 0.156 (3) 0.057 (2) 0.072 (2) −0.003 (2) 0.072 (2) −0.0001 (18)
C27 0.215 (5) 0.065 (2) 0.087 (2) 0.015 (3) 0.088 (3) 0.014 (2)
O1A 0.1121 (17) 0.0722 (14) 0.0350 (10) −0.0027 (11) 0.0252 (10) 0.0048 (10)
O2A 0.0722 (14) 0.0668 (14) 0.0740 (13) −0.0165 (11) 0.0329 (10) −0.0276 (11)
O3A 0.160 (2) 0.0531 (15) 0.0759 (15) 0.0002 (13) 0.0538 (15) 0.0073 (13)
C1A 0.072 (2) 0.0428 (17) 0.0463 (15) −0.0049 (15) 0.0251 (14) −0.0036 (13)
C2A 0.061 (2) 0.074 (2) 0.0643 (18) −0.0085 (16) 0.0289 (15) −0.0163 (17)
C3A 0.069 (2) 0.075 (2) 0.0588 (17) −0.0219 (17) 0.0224 (15) −0.0186 (17)
C4A 0.073 (2) 0.0475 (18) 0.0463 (15) −0.0014 (16) 0.0273 (15) −0.0013 (14)
C5A 0.067 (2) 0.0558 (19) 0.0552 (16) 0.0015 (15) 0.0241 (15) −0.0093 (15)
C6A 0.0602 (19) 0.064 (2) 0.0586 (17) −0.0049 (16) 0.0182 (15) −0.0082 (16)
C7A 0.085 (2) 0.056 (2) 0.0453 (15) −0.0053 (16) 0.0231 (14) −0.0045 (14)
C8A 0.080 (2) 0.0552 (19) 0.0351 (14) 0.0022 (15) 0.0189 (13) −0.0016 (13)
C9A 0.0621 (18) 0.0490 (18) 0.0422 (14) 0.0017 (13) 0.0200 (12) −0.0006 (13)
C10A 0.0636 (18) 0.0516 (19) 0.0366 (13) 0.0010 (14) 0.0177 (12) −0.0045 (14)
C11A 0.086 (2) 0.059 (2) 0.0448 (15) −0.0015 (16) 0.0300 (15) 0.0005 (15)
C12A 0.094 (2) 0.051 (2) 0.0571 (17) −0.0006 (16) 0.0315 (15) −0.0081 (15)
C13A 0.095 (2) 0.048 (2) 0.0507 (17) 0.0035 (16) 0.0271 (16) 0.0075 (16)
C14A 0.139 (3) 0.066 (2) 0.0494 (17) 0.011 (2) 0.0480 (19) 0.0085 (17)
C15A 0.108 (3) 0.058 (2) 0.0445 (16) 0.0095 (17) 0.0330 (16) 0.0047 (15)
C16A 0.203 (5) 0.060 (3) 0.118 (3) −0.006 (3) 0.082 (3) −0.006 (2)
C17A 0.075 (2) 0.066 (2) 0.083 (2) −0.0095 (18) 0.0219 (17) −0.0221 (18)
C18A 0.069 (2) 0.0463 (18) 0.0576 (17) −0.0063 (15) 0.0204 (15) −0.0087 (16)
C19A 0.087 (2) 0.077 (3) 0.0570 (19) 0.0107 (18) 0.0135 (17) 0.0019 (18)
C20A 0.121 (3) 0.108 (3) 0.0535 (19) 0.014 (3) 0.009 (2) −0.028 (2)
C21A 0.118 (3) 0.080 (3) 0.084 (3) 0.008 (2) 0.013 (2) −0.032 (2)
C22A 0.116 (3) 0.060 (2) 0.085 (2) 0.022 (2) 0.016 (2) −0.006 (2)
C23A 0.094 (2) 0.069 (2) 0.0540 (18) 0.0051 (19) 0.0150 (17) −0.0060 (18)
C24A 0.076 (2) 0.0519 (19) 0.0397 (14) −0.0051 (14) 0.0214 (13) −0.0058 (14)
C25A 0.0711 (19) 0.059 (2) 0.0409 (15) −0.0023 (15) 0.0217 (13) 0.0021 (14)
C26A 0.099 (2) 0.058 (2) 0.0440 (15) −0.0051 (16) 0.0271 (15) −0.0009 (15)
C27A 0.122 (3) 0.060 (2) 0.0555 (17) −0.0166 (18) 0.0302 (18) 0.0059 (16)
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Geometric parameters (Å, º)

O1—C25 1.228 (3) O1A—C25A 1.224 (3)
O2—C1 1.382 (3) O2A—C1A 1.380 (3)
O2—C17 1.410 (3) O2A—C17A 1.406 (3)
O3—C13 1.366 (3) O3A—C13A 1.362 (3)
O3—C16 1.399 (4) O3A—C16A 1.414 (4)
C1—C6 1.371 (4) C1A—C2A 1.371 (4)
C1—C2 1.372 (4) C1A—C6A 1.372 (4)
C2—C3 1.399 (4) C2A—C3A 1.376 (4)
C2—H2 0.9300 C2A—H2A 0.9300
C3—C4 1.358 (4) C3A—C4A 1.390 (4)
C3—H3 0.9300 C3A—H3A 0.9300
C4—C5 1.373 (4) C4A—C5A 1.361 (4)
C4—C7 1.521 (4) C4A—C7A 1.522 (4)
C5—C6 1.392 (4) C5A—C6A 1.387 (4)
C5—H5 0.9300 C5A—H5A 0.9300
C6—H6 0.9300 C6A—H6A 0.9300
C7—C26 1.472 (4) C7A—C26A 1.502 (4)
C7—C8 1.497 (4) C7A—C8A 1.504 (4)
C7—H7 0.9800 C7A—H7A 0.9800
C8—C9 1.506 (3) C8A—C9A 1.498 (3)
C8—H8A 0.9700 C8A—H8A1 0.9700
C8—H8B 0.9700 C8A—H8A2 0.9700
C9—C24 1.352 (3) C9A—C24A 1.355 (3)
C9—C10 1.463 (3) C9A—C10A 1.467 (3)
C10—C11 1.390 (3) C10A—C11A 1.383 (3)
C10—C15 1.406 (3) C10A—C15A 1.402 (3)
C11—C12 1.369 (4) C11A—C12A 1.369 (4)
C11—H11 0.9300 C11A—H11A 0.9300
C12—C13 1.380 (4) C12A—C13A 1.377 (4)
C12—H12 0.9300 C12A—H12A 0.9300
C13—C14 1.376 (4) C13A—C14A 1.362 (4)
C14—C15 1.368 (4) C14A—C15A 1.378 (4)
C14—H14 0.9300 C14A—H14A 0.9300
C15—H15 0.9300 C15A—H15A 0.9300
C16—H16A 0.9600 C16A—H16D 0.9600
C16—H16B 0.9600 C16A—H16E 0.9600
C16—H16C 0.9600 C16A—H16F 0.9600
C17—C18 1.503 (4) C17A—C18A 1.488 (4)
C17—H17A 0.9700 C17A—H17C 0.9700
C17—H17B 0.9700 C17A—H17D 0.9700
C18—C23 1.362 (4) C18A—C23A 1.377 (4)
C18—C19 1.378 (4) C18A—C19A 1.379 (4)
C19—C20 1.380 (4) C19A—C20A 1.377 (4)
C19—H19 0.9300 C19A—H19A 0.9300
C20—C21 1.344 (5) C20A—C21A 1.355 (5)
C20—H20 0.9300 C20A—H20A 0.9300
C21—C22 1.345 (5) C21A—C22A 1.344 (4)
C21—H21 0.9300 C21A—H21A 0.9300
C22—C23 1.367 (4) C22A—C23A 1.369 (4)
C22—H22 0.9300 C22A—H22A 0.9300
C23—H23 0.9300 C23A—H23A 0.9300
C24—C25 1.445 (4) C24A—C25A 1.449 (4)
C24—H24 0.9300 C24A—H24A 0.9300
C25—C26 1.510 (4) C25A—C26A 1.511 (4)
C26—C27 1.502 (4) C26A—C27A 1.507 (4)
C26—H26 0.9800 C26A—H26A 0.9800
C27—H27A 0.9600 C27A—H27D 0.9600
C27—H27B 0.9600 C27A—H27E 0.9600
C27—H27C 0.9600 C27A—H27F 0.9600
C1—O2—C17 117.8 (2) C1A—O2A—C17A 118.6 (2)
C13—O3—C16 119.7 (2) C13A—O3A—C16A 119.0 (2)
C6—C1—C2 119.9 (3) C2A—C1A—C6A 119.6 (3)
C6—C1—O2 114.8 (3) C2A—C1A—O2A 114.7 (2)
C2—C1—O2 125.3 (3) C6A—C1A—O2A 125.7 (3)
C1—C2—C3 119.6 (3) C1A—C2A—C3A 120.1 (3)
C1—C2—H2 120.2 C1A—C2A—H2A 120.0
C3—C2—H2 120.2 C3A—C2A—H2A 120.0
C4—C3—C2 121.7 (3) C2A—C3A—C4A 121.4 (3)
C4—C3—H3 119.1 C2A—C3A—H3A 119.3
C2—C3—H3 119.1 C4A—C3A—H3A 119.3
C3—C4—C5 117.6 (3) C5A—C4A—C3A 117.3 (3)
C3—C4—C7 122.0 (3) C5A—C4A—C7A 121.6 (3)
C5—C4—C7 120.4 (3) C3A—C4A—C7A 121.1 (3)
C4—C5—C6 122.2 (3) C4A—C5A—C6A 122.2 (3)
C4—C5—H5 118.9 C4A—C5A—H5A 118.9
C6—C5—H5 118.9 C6A—C5A—H5A 118.9
C1—C6—C5 119.0 (3) C1A—C6A—C5A 119.4 (3)
C1—C6—H6 120.5 C1A—C6A—H6A 120.3
C5—C6—H6 120.5 C5A—C6A—H6A 120.3
C26—C7—C8 113.8 (3) C26A—C7A—C8A 113.1 (2)
C26—C7—C4 113.9 (3) C26A—C7A—C4A 113.4 (2)
C8—C7—C4 112.2 (2) C8A—C7A—C4A 113.2 (2)
C26—C7—H7 105.3 C26A—C7A—H7A 105.4
C8—C7—H7 105.3 C8A—C7A—H7A 105.4
C4—C7—H7 105.3 C4A—C7A—H7A 105.4
C7—C8—C9 115.0 (2) C9A—C8A—C7A 114.1 (2)
C7—C8—H8A 108.5 C9A—C8A—H8A1 108.7
C9—C8—H8A 108.5 C7A—C8A—H8A1 108.7
C7—C8—H8B 108.5 C9A—C8A—H8A2 108.7
C9—C8—H8B 108.5 C7A—C8A—H8A2 108.7
H8A—C8—H8B 107.5 H8A1—C8A—H8A2 107.6
C24—C9—C10 122.4 (2) C24A—C9A—C10A 122.3 (2)
C24—C9—C8 118.9 (2) C24A—C9A—C8A 119.0 (2)
C10—C9—C8 118.7 (2) C10A—C9A—C8A 118.7 (2)
C11—C10—C15 115.9 (2) C11A—C10A—C15A 115.9 (2)
C11—C10—C9 122.9 (2) C11A—C10A—C9A 122.4 (2)
C15—C10—C9 121.2 (2) C15A—C10A—C9A 121.7 (2)
C12—C11—C10 122.5 (3) C12A—C11A—C10A 123.2 (2)
C12—C11—H11 118.7 C12A—C11A—H11A 118.4
C10—C11—H11 118.7 C10A—C11A—H11A 118.4
C11—C12—C13 120.4 (3) C11A—C12A—C13A 119.6 (3)
C11—C12—H12 119.8 C11A—C12A—H12A 120.2
C13—C12—H12 119.8 C13A—C12A—H12A 120.2
O3—C13—C14 116.1 (3) O3A—C13A—C14A 116.2 (3)
O3—C13—C12 125.5 (3) O3A—C13A—C12A 124.9 (3)
C14—C13—C12 118.4 (3) C14A—C13A—C12A 118.9 (3)
C15—C14—C13 121.1 (3) C13A—C14A—C15A 121.5 (3)
C15—C14—H14 119.4 C13A—C14A—H14A 119.3
C13—C14—H14 119.4 C15A—C14A—H14A 119.3
C14—C15—C10 121.5 (3) C14A—C15A—C10A 120.8 (3)
C14—C15—H15 119.2 C14A—C15A—H15A 119.6
C10—C15—H15 119.2 C10A—C15A—H15A 119.6
O3—C16—H16A 109.5 O3A—C16A—H16D 109.5
O3—C16—H16B 109.5 O3A—C16A—H16E 109.5
H16A—C16—H16B 109.5 H16D—C16A—H16E 109.5
O3—C16—H16C 109.5 O3A—C16A—H16F 109.5
H16A—C16—H16C 109.5 H16D—C16A—H16F 109.5
H16B—C16—H16C 109.5 H16E—C16A—H16F 109.5
O2—C17—C18 108.1 (3) O2A—C17A—C18A 108.7 (2)
O2—C17—H17A 110.1 O2A—C17A—H17C 110.0
C18—C17—H17A 110.1 C18A—C17A—H17C 110.0
O2—C17—H17B 110.1 O2A—C17A—H17D 110.0
C18—C17—H17B 110.1 C18A—C17A—H17D 110.0
H17A—C17—H17B 108.4 H17C—C17A—H17D 108.3
C23—C18—C19 117.8 (3) C23A—C18A—C19A 117.3 (3)
C23—C18—C17 121.7 (3) C23A—C18A—C17A 121.0 (3)
C19—C18—C17 120.5 (3) C19A—C18A—C17A 121.5 (3)
C18—C19—C20 119.7 (3) C20A—C19A—C18A 120.1 (3)
C18—C19—H19 120.2 C20A—C19A—H19A 119.9
C20—C19—H19 120.2 C18A—C19A—H19A 119.9
C21—C20—C19 121.3 (3) C21A—C20A—C19A 121.5 (3)
C21—C20—H20 119.4 C21A—C20A—H20A 119.2
C19—C20—H20 119.4 C19A—C20A—H20A 119.2
C20—C21—C22 119.3 (4) C22A—C21A—C20A 118.7 (3)
C20—C21—H21 120.4 C22A—C21A—H21A 120.7
C22—C21—H21 120.4 C20A—C21A—H21A 120.7
C21—C22—C23 120.6 (4) C21A—C22A—C23A 121.2 (3)
C21—C22—H22 119.7 C21A—C22A—H22A 119.4
C23—C22—H22 119.7 C23A—C22A—H22A 119.4
C18—C23—C22 121.4 (3) C22A—C23A—C18A 121.2 (3)
C18—C23—H23 119.3 C22A—C23A—H23A 119.4
C22—C23—H23 119.3 C18A—C23A—H23A 119.4
C9—C24—C25 123.6 (3) C9A—C24A—C25A 124.0 (2)
C9—C24—H24 118.2 C9A—C24A—H24A 118.0
C25—C24—H24 118.2 C25A—C24A—H24A 118.0
O1—C25—C24 120.8 (3) O1A—C25A—C24A 120.5 (2)
O1—C25—C26 120.9 (3) O1A—C25A—C26A 121.3 (3)
C24—C25—C26 118.0 (2) C24A—C25A—C26A 118.1 (2)
C7—C26—C27 117.1 (3) C7A—C26A—C27A 115.5 (2)
C7—C26—C25 111.6 (3) C7A—C26A—C25A 110.6 (2)
C27—C26—C25 112.6 (2) C27A—C26A—C25A 112.3 (2)
C7—C26—H26 104.8 C7A—C26A—H26A 105.9
C27—C26—H26 104.8 C27A—C26A—H26A 105.9
C25—C26—H26 104.8 C25A—C26A—H26A 105.9
C26—C27—H27A 109.5 C26A—C27A—H27D 109.5
C26—C27—H27B 109.5 C26A—C27A—H27E 109.5
H27A—C27—H27B 109.5 H27D—C27A—H27E 109.5
C26—C27—H27C 109.5 C26A—C27A—H27F 109.5
H27A—C27—H27C 109.5 H27D—C27A—H27F 109.5
H27B—C27—H27C 109.5 H27E—C27A—H27F 109.5
C17—O2—C1—C6 179.5 (2) C17A—O2A—C1A—C2A −179.5 (2)
C17—O2—C1—C2 −0.2 (4) C17A—O2A—C1A—C6A 0.1 (4)
C6—C1—C2—C3 −0.2 (4) C6A—C1A—C2A—C3A −0.4 (4)
O2—C1—C2—C3 179.5 (2) O2A—C1A—C2A—C3A 179.2 (2)
C1—C2—C3—C4 0.6 (4) C1A—C2A—C3A—C4A −1.3 (4)
C2—C3—C4—C5 −0.3 (4) C2A—C3A—C4A—C5A 1.9 (4)
C2—C3—C4—C7 179.1 (2) C2A—C3A—C4A—C7A −177.6 (2)
C3—C4—C5—C6 −0.3 (4) C3A—C4A—C5A—C6A −0.7 (4)
C7—C4—C5—C6 −179.7 (2) C7A—C4A—C5A—C6A 178.7 (2)
C2—C1—C6—C5 −0.4 (4) C2A—C1A—C6A—C5A 1.5 (4)
O2—C1—C6—C5 179.9 (2) O2A—C1A—C6A—C5A −178.1 (2)
C4—C5—C6—C1 0.7 (4) C4A—C5A—C6A—C1A −0.9 (4)
C3—C4—C7—C26 118.8 (3) C5A—C4A—C7A—C26A −118.0 (3)
C5—C4—C7—C26 −61.8 (4) C3A—C4A—C7A—C26A 61.4 (4)
C3—C4—C7—C8 −110.1 (3) C5A—C4A—C7A—C8A 111.5 (3)
C5—C4—C7—C8 69.2 (4) C3A—C4A—C7A—C8A −69.1 (3)
C26—C7—C8—C9 −44.2 (4) C26A—C7A—C8A—C9A 47.7 (3)
C4—C7—C8—C9 −175.3 (2) C4A—C7A—C8A—C9A 178.4 (2)
C7—C8—C9—C24 16.6 (4) C7A—C8A—C9A—C24A −20.0 (4)
C7—C8—C9—C10 −166.5 (2) C7A—C8A—C9A—C10A 161.4 (2)
C24—C9—C10—C11 −16.0 (4) C24A—C9A—C10A—C11A 20.8 (4)
C8—C9—C10—C11 167.3 (2) C8A—C9A—C10A—C11A −160.6 (2)
C24—C9—C10—C15 161.8 (3) C24A—C9A—C10A—C15A −156.7 (3)
C8—C9—C10—C15 −14.9 (4) C8A—C9A—C10A—C15A 21.8 (4)
C15—C10—C11—C12 −2.1 (4) C15A—C10A—C11A—C12A 0.8 (4)
C9—C10—C11—C12 175.9 (3) C9A—C10A—C11A—C12A −176.8 (3)
C10—C11—C12—C13 0.3 (4) C10A—C11A—C12A—C13A 1.7 (4)
C16—O3—C13—C14 −166.5 (3) C16A—O3A—C13A—C14A 173.7 (3)
C16—O3—C13—C12 13.2 (5) C16A—O3A—C13A—C12A −7.3 (5)
C11—C12—C13—O3 −178.0 (3) C11A—C12A—C13A—O3A 178.2 (3)
C11—C12—C13—C14 1.7 (4) C11A—C12A—C13A—C14A −2.8 (4)
O3—C13—C14—C15 178.0 (3) O3A—C13A—C14A—C15A −179.5 (3)
C12—C13—C14—C15 −1.8 (4) C12A—C13A—C14A—C15A 1.4 (5)
C13—C14—C15—C10 −0.1 (4) C13A—C14A—C15A—C10A 1.3 (5)
C11—C10—C15—C14 2.0 (4) C11A—C10A—C15A—C14A −2.3 (4)
C9—C10—C15—C14 −176.0 (3) C9A—C10A—C15A—C14A 175.4 (3)
C1—O2—C17—C18 −173.3 (2) C1A—O2A—C17A—C18A 169.1 (2)
O2—C17—C18—C23 51.4 (4) O2A—C17A—C18A—C23A −55.5 (4)
O2—C17—C18—C19 −130.6 (3) O2A—C17A—C18A—C19A 128.7 (3)
C23—C18—C19—C20 1.1 (5) C23A—C18A—C19A—C20A 0.1 (5)
C17—C18—C19—C20 −177.0 (3) C17A—C18A—C19A—C20A 176.1 (3)
C18—C19—C20—C21 −0.6 (6) C18A—C19A—C20A—C21A −0.1 (6)
C19—C20—C21—C22 −0.2 (7) C19A—C20A—C21A—C22A 0.6 (6)
C20—C21—C22—C23 0.5 (7) C20A—C21A—C22A—C23A −1.0 (6)
C19—C18—C23—C22 −0.8 (5) C21A—C22A—C23A—C18A 1.0 (6)
C17—C18—C23—C22 177.2 (3) C19A—C18A—C23A—C22A −0.5 (5)
C21—C22—C23—C18 0.1 (7) C17A—C18A—C23A—C22A −176.5 (3)
C10—C9—C24—C25 −173.4 (2) C10A—C9A—C24A—C25A 176.1 (2)
C8—C9—C24—C25 3.4 (4) C8A—C9A—C24A—C25A −2.4 (4)
C9—C24—C25—O1 177.9 (3) C9A—C24A—C25A—O1A −179.3 (3)
C9—C24—C25—C26 4.0 (4) C9A—C24A—C25A—C26A −3.0 (4)
C8—C7—C26—C27 −178.1 (3) C8A—C7A—C26A—C27A 179.4 (2)
C4—C7—C26—C27 −47.8 (4) C4A—C7A—C26A—C27A 48.9 (4)
C8—C7—C26—C25 50.2 (4) C8A—C7A—C26A—C25A −51.6 (3)
C4—C7—C26—C25 −179.5 (3) C4A—C7A—C26A—C25A 177.8 (2)
O1—C25—C26—C7 155.3 (3) O1A—C25A—C26A—C7A −153.9 (3)
C24—C25—C26—C7 −30.8 (4) C24A—C25A—C26A—C7A 29.9 (4)
O1—C25—C26—C27 21.3 (5) O1A—C25A—C26A—C27A −23.3 (4)
C24—C25—C26—C27 −164.8 (3) C24A—C25A—C26A—C27A 160.5 (3)
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Hydrogen-bond geometry (Å, º)

Cg3 and Cg8 are the centroids of rings C10-C15 and C10A-C15A, respectively.

D—H···A D—H H···A D···A D—H···A
C2A—H2A···Cg3i 0.93 2.87 3.707 (3) 150
C16A—H16E···Cg8ii 0.96 2.92 3.866 (5) 168
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Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

References

  1. Asiri, A. M. (2003). Bull. Korean Chem. Soc. 24, 426–430.
  2. Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Ezhilarasi, K. S., Reuben Jonathan, D., Sathya, S., Prathebha, K. & Usha, G. (2014). Acta Cryst. E70, o608–o609. [DOI] [PMC free article] [PubMed]
  4. Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
  5. Ferrer, R., Lobo, G., Gamboa, N., Rodrigues, J., Abramjuk, C., Jung, K., Lein, M. & Charris, J. E. (2009). Sci. Pharm. 77, 725–741.
  6. Forestier, S., Moire, C. & Lang, G. (1989). US Patent No. 4867964.
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014025390/su5016sup1.cif

e-71-00016-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025390/su5016Isup2.hkl

e-71-00016-Isup2.hkl (432.8KB, hkl)
Click here for additional data file. (8.2KB, cml)

Supporting information file. DOI: 10.1107/S2056989014025390/su5016Isup3.cml

CCDC reference: 1035112

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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