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ISSN: 2056-9890

(3-Ethyl-6,7-dimeth­­oxy­naphthalen-1-yl)(phen­yl)methanone

aSchool of Chemistry, Bharathidasan University, Thiruchirapalli, Tamil Nadu 620 024, India, and bDepartment of Advanced Technology Fusion, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143 701, Republic of Korea
*Correspondence e-mail: sams76@gmail.com

(Received 28 December 2011; accepted 3 February 2012; online 10 February 2012)

The asymetric unit of the title mol­ecule, C21H20O3, contains two crystallographically independent mol­ecules, A and B, which differ in the orientation of the ethyl group substituted on the naphthalene system; the dihedral angles between the ethyl group and the naphthalene system are 7.4 (3) and 68.1 (3)°, respectively, for mol­ecules A and B. The dihedral angles between the benzoyl and naphthalene groups are 64.7 (7) and 69.4 (8)°, respectively, for mol­ecules A and B. The crystal structure features four aromatic ππ stacking interactions [centroid–centroid distances = 4.181 (1), 3.891 (1), 4.423 (1) and 4.249 (1) Å].

Related literature

For the biological activities of naphthalene compounds, see: Dekoning et al. (2003[Dekoning, C. B., Rousseau, A. L. & Vanotterlo, W. A. (2003). Tetrahedron, 59, 7-36.]); Alvarez et al. (2007[Alvarez, C., Alvarez, R., Corchete, P., Perez-Melero, C., Pelaez, R. & Medarde, M. (2007). Bioorg. Med. Chem. Lett. 17, 3417-3420.]). For related crystal structures, see: Watanabe et al. (2010[Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615.]); Thenmozhi et al. (2008[Thenmozhi, S., SubbiahPandi, A., Ranjith, S., Clement, J. A. & Mohana­Krishnan, A. K. (2008). Acta Cryst. E64, o2432.]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20O3

  • Mr = 320.37

  • Triclinic, [P \overline 1]

  • a = 9.9012 (2) Å

  • b = 11.3431 (2) Å

  • c = 16.0701 (3) Å

  • α = 100.170 (1)°

  • β = 90.487 (1)°

  • γ = 98.373 (1)°

  • V = 1756.46 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.12 × 0.08 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.869, Tmax = 1.483

  • 33428 measured reflections

  • 7706 independent reflections

  • 4854 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.214

  • S = 1.05

  • 7706 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Polysubstituted napthalenes exhibit a wide range of biological activities such as antiviral, anti-diabetic, anti-malarial and anti-tumor activities (Dekoning et al., 2003). Naphthylphenstatin (dimethoxy benzoylnaphthalene), a compound similar to the title compound, is one of the naphthalene compounds which has the activity of tubulin polymerization inhibition and cytotoxic activities (Alvarez et al., 2007).

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). The corresponding bond lengths and angles of the two molecules agree with each other, and are comparable to those observed in the structures of 2,7-dimethoxy-1-(4-nitrobenzoyl)-naphthalene (Watanabe et al., 2010) and naphthalene-2,3-diylbis(2-thienyl)-methanone (Thenmozhi et al., 2008). The two independent molecules differ in the orientations of ethyl units with respect to the naphthalene ring system. The dihedral angle of these ethyl units and naphthalene rings A and B respectively are 7.4 (3) and 68.1 (3)°. The dihedral angles between the benzoyl group and naphthalene ring system are 64.7 (7) and 69.4 (8)° for molecules A and B, respectively.

The title molecule do not show any classical hydrogen bonds (Fig. 2). But the molecules are stabilized in the unit cell packing with help of weak ππ interactions {[Cg1···Cg2] = 4.181 (1) Å (1 - x, 2 - y, -z); [Cg2···Cg2] = 3.891 (1) Å (1 - x, 2 - y, -z); [Cg3···Cg4] = 4.423 (1) Å (-x, -y, 1 - z) and [Cg4···Cg4] = 4.249 (1) Å (-x, -y, 1 - z); here, Cg is the centroid of the benzene rings, Cg1 = C1A–C6A, Cg2 = C5A–C10A, Cg3 = C1B–C6B and Cg4 = C5B–C10B}.

Related literature top

For the biological activities of naphthalene compounds, see: Dekoning et al. (2003); Alvarez et al. (2007). For related crystal structures, see: Watanabe et al. (2010); Thenmozhi et al. (2008). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1995).

Experimental top

The title compound was synthesized in 83% yield (0.1 g) by heating a mixture of 4,5-dimethoxy-2-phenylethynylbenzaldehyde (0.1 g, 0.3 mmol) and n-butyraldehyde (0.027 g, 0.37 mmol) in 1,2-dichloroethane for 3 h under reflux. The resulting product was recrystallized from methanol which produced light brown color crystals.

Refinement top

The terminal 12 A atom shows higher thermal motion due to free rotation which reflects in abnormal bond length (C11A—C12A). H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å for aromatic H, C—H = 0.97 Å for methylene H and 0.96 Å for methyl H atoms. The Uiso parameters for H atoms were constrained to be 1.5Ueq of the carrier atom for the methyl H atoms and 1.2Ueq of the carrier atom for the remaining H atoms.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SMART (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the title molecule with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H-atoms were removed for clarity.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the a axis.
(3-Ethyl-6,7-dimethoxynaphthalen-1-yl)(phenyl)methanone top
Crystal data top
C21H20O3Z = 4
Mr = 320.37F(000) = 680
Triclinic, P1Dx = 1.211 Mg m3
a = 9.9012 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3431 (2) ÅCell parameters from 7706 reflections
c = 16.0701 (3) Åθ = 1.8–27.1°
α = 100.170 (1)°µ = 0.08 mm1
β = 90.487 (1)°T = 293 K
γ = 98.373 (1)°Needle, pale-brown
V = 1756.46 (6) Å30.12 × 0.08 × 0.06 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
7706 independent reflections
Radiation source: fine-focus sealed tube4854 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 27.1°, θmin = 1.8°
Absorption correction: part of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
h = 1212
Tmin = 0.869, Tmax = 1.483k = 1414
33428 measured reflectionsl = 020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.214H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1046P)2 + 0.3934P]
where P = (Fo2 + 2Fc2)/3
7706 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C21H20O3γ = 98.373 (1)°
Mr = 320.37V = 1756.46 (6) Å3
Triclinic, P1Z = 4
a = 9.9012 (2) ÅMo Kα radiation
b = 11.3431 (2) ŵ = 0.08 mm1
c = 16.0701 (3) ÅT = 293 K
α = 100.170 (1)°0.12 × 0.08 × 0.06 mm
β = 90.487 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
7706 independent reflections
Absorption correction: part of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
4854 reflections with I > 2σ(I)
Tmin = 0.869, Tmax = 1.483Rint = 0.034
33428 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.214H-atom parameters constrained
S = 1.05Δρmax = 0.63 e Å3
7706 reflectionsΔρmin = 0.32 e Å3
433 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.2799 (2)0.67052 (17)0.10690 (11)0.0917 (6)
O2A0.6797 (2)0.71872 (16)0.07109 (12)0.0927 (6)
O3A0.80443 (17)0.93243 (15)0.06671 (10)0.0763 (5)
C1A0.4076 (2)0.85790 (19)0.17247 (13)0.0578 (5)
C2A0.3801 (2)0.9548 (2)0.23037 (14)0.0636 (5)
H2A0.31790.94100.27190.076*
C3A0.4420 (2)1.0739 (2)0.22952 (14)0.0656 (5)
C4A0.5398 (2)1.09145 (18)0.17097 (13)0.0598 (5)
H4A0.58451.16940.17090.072*
C5A0.5745 (2)0.99481 (17)0.11092 (12)0.0532 (4)
C6A0.5062 (2)0.87582 (18)0.10996 (12)0.0543 (5)
C7A0.5410 (2)0.78111 (19)0.04753 (14)0.0630 (5)
H7A0.49630.70250.04520.076*
C8A0.6388 (2)0.8033 (2)0.00900 (14)0.0655 (5)
C9A0.7086 (2)0.9229 (2)0.00690 (13)0.0600 (5)
C10A0.6768 (2)1.01583 (18)0.05192 (12)0.0562 (5)
H10A0.72271.09380.05340.067*
C11A0.3969 (4)1.1763 (2)0.2907 (2)0.1063 (11)
H11A0.30151.17640.27650.128*
H11B0.39961.15380.34610.128*
C12A0.4551 (8)1.2875 (4)0.3001 (4)0.272 (5)
H12A0.40931.33680.34220.408*
H12B0.45031.31560.24730.408*
H12C0.54911.29290.31770.408*
C13A0.3238 (2)0.7369 (2)0.17281 (14)0.0641 (5)
C14A0.2884 (2)0.69894 (18)0.25523 (14)0.0615 (5)
C15A0.1637 (2)0.6265 (2)0.26026 (17)0.0752 (6)
H15A0.10580.60110.21260.090*
C16A0.1261 (3)0.5923 (2)0.3359 (2)0.0930 (9)
H16A0.04140.54630.33970.112*
C17A0.2131 (4)0.6259 (3)0.4058 (2)0.0963 (9)
H17A0.18660.60360.45690.116*
C18A0.3399 (3)0.6928 (2)0.40032 (17)0.0895 (8)
H18A0.40030.71230.44700.107*
C19A0.3771 (3)0.7307 (2)0.32593 (15)0.0728 (6)
H19A0.46150.77760.32290.087*
C20A0.8778 (3)1.0491 (2)0.06818 (17)0.0832 (7)
H20A0.94221.04380.11250.125*
H20B0.92571.07990.01480.125*
H20C0.81521.10270.07820.125*
C21A0.6212 (4)0.5960 (3)0.0752 (2)0.1215 (13)
H21A0.65930.54630.12100.182*
H21B0.52410.58780.08440.182*
H21C0.64060.57080.02300.182*
O1B1.1025 (2)0.65955 (17)0.62049 (11)0.0913 (6)
O2B0.6969 (2)0.70067 (16)0.44345 (12)0.0897 (5)
O3B0.66014 (18)0.91587 (15)0.43543 (10)0.0793 (5)
C1B1.0365 (2)0.84866 (19)0.67860 (13)0.0600 (5)
C2B1.0984 (2)0.9478 (2)0.73535 (15)0.0707 (6)
H2B1.15460.93560.77880.085*
C3B1.0797 (3)1.0672 (2)0.72990 (16)0.0745 (6)
C4B0.9920 (2)1.0823 (2)0.66790 (14)0.0670 (6)
H4B0.97851.16040.66350.080*
C5B0.9211 (2)0.98404 (18)0.61035 (13)0.0563 (5)
C6B0.94478 (19)0.86463 (18)0.61375 (12)0.0549 (5)
C7B0.8703 (2)0.7674 (2)0.55581 (13)0.0615 (5)
H7B0.88540.68850.55650.074*
C8B0.7773 (2)0.7878 (2)0.49950 (14)0.0646 (5)
C9B0.7553 (2)0.9087 (2)0.49535 (13)0.0619 (5)
C10B0.8264 (2)1.0031 (2)0.54951 (13)0.0602 (5)
H10B0.81261.08170.54660.072*
C11B1.1522 (4)1.1752 (3)0.7944 (2)0.1160 (12)
H11C1.08381.22140.82070.139*
H11D1.19591.14410.83850.139*
C12B1.2469 (6)1.2507 (4)0.7619 (3)0.175 (2)
H12D1.28701.31500.80620.262*
H12E1.20451.28430.71940.262*
H12F1.31671.20670.73710.262*
C13B1.0760 (2)0.7286 (2)0.68383 (15)0.0654 (5)
C14B1.0863 (2)0.69243 (19)0.76813 (14)0.0641 (5)
C15B1.1802 (3)0.6170 (2)0.78166 (19)0.0832 (7)
H15B1.23760.59170.73870.100*
C16B1.1886 (4)0.5797 (3)0.8586 (2)0.1031 (10)
H16B1.25330.53100.86760.124*
C17B1.1027 (4)0.6135 (3)0.9214 (2)0.1047 (10)
H17B1.10880.58790.97300.126*
C18B1.0082 (3)0.6850 (3)0.90836 (17)0.0912 (8)
H18B0.94830.70640.95070.109*
C19B1.0006 (3)0.7259 (2)0.83253 (15)0.0728 (6)
H19B0.93720.77640.82490.087*
C20B0.6381 (3)1.0335 (3)0.42544 (18)0.0891 (8)
H20D0.56911.02700.38190.134*
H20E0.72171.07750.41000.134*
H20F0.60881.07560.47770.134*
C21B0.7066 (4)0.5784 (3)0.4460 (2)0.1110 (11)
H21D0.64520.52670.40380.166*
H21E0.68270.56140.50090.166*
H21F0.79850.56390.43500.166*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.1024 (13)0.0857 (12)0.0727 (11)0.0220 (10)0.0048 (10)0.0054 (9)
O2A0.1159 (14)0.0642 (10)0.0920 (12)0.0127 (10)0.0357 (11)0.0028 (9)
O3A0.0804 (11)0.0747 (10)0.0719 (10)0.0083 (8)0.0221 (8)0.0101 (8)
C1A0.0552 (11)0.0585 (11)0.0594 (11)0.0050 (9)0.0003 (9)0.0126 (9)
C2A0.0607 (12)0.0644 (13)0.0673 (13)0.0084 (10)0.0111 (10)0.0161 (10)
C3A0.0695 (13)0.0597 (12)0.0679 (13)0.0129 (10)0.0111 (11)0.0092 (10)
C4A0.0617 (12)0.0508 (11)0.0663 (12)0.0064 (9)0.0032 (10)0.0099 (9)
C5A0.0514 (10)0.0535 (10)0.0556 (11)0.0082 (8)0.0021 (8)0.0117 (8)
C6A0.0544 (11)0.0541 (11)0.0543 (11)0.0074 (8)0.0037 (8)0.0100 (8)
C7A0.0692 (13)0.0531 (11)0.0650 (12)0.0055 (10)0.0021 (10)0.0093 (9)
C8A0.0740 (14)0.0572 (12)0.0643 (13)0.0139 (10)0.0049 (11)0.0046 (10)
C9A0.0599 (12)0.0650 (12)0.0561 (11)0.0098 (10)0.0044 (9)0.0127 (9)
C10A0.0564 (11)0.0546 (11)0.0584 (11)0.0069 (9)0.0001 (9)0.0132 (9)
C11A0.140 (3)0.0658 (16)0.113 (2)0.0221 (17)0.059 (2)0.0075 (15)
C12A0.400 (10)0.086 (3)0.286 (7)0.026 (4)0.246 (8)0.049 (4)
C13A0.0595 (12)0.0598 (12)0.0693 (13)0.0007 (10)0.0000 (10)0.0087 (10)
C14A0.0607 (12)0.0509 (11)0.0720 (13)0.0039 (9)0.0040 (10)0.0116 (9)
C15A0.0696 (14)0.0587 (13)0.0935 (17)0.0024 (11)0.0076 (12)0.0131 (12)
C16A0.099 (2)0.0681 (15)0.112 (2)0.0038 (14)0.0287 (18)0.0302 (15)
C17A0.132 (3)0.0720 (16)0.092 (2)0.0124 (17)0.0279 (19)0.0343 (15)
C18A0.122 (2)0.0728 (16)0.0755 (16)0.0129 (16)0.0027 (15)0.0212 (13)
C19A0.0747 (15)0.0638 (13)0.0792 (15)0.0031 (11)0.0011 (12)0.0172 (11)
C20A0.0834 (17)0.0832 (17)0.0845 (17)0.0066 (13)0.0219 (13)0.0234 (13)
C21A0.158 (3)0.0627 (16)0.132 (3)0.0075 (18)0.050 (2)0.0104 (17)
O1B0.1117 (14)0.0941 (13)0.0770 (11)0.0484 (11)0.0196 (10)0.0116 (9)
O2B0.1035 (13)0.0690 (11)0.0878 (12)0.0079 (9)0.0265 (10)0.0044 (9)
O3B0.0847 (11)0.0782 (11)0.0740 (10)0.0153 (9)0.0169 (9)0.0097 (8)
C1B0.0540 (11)0.0652 (13)0.0611 (12)0.0101 (9)0.0068 (9)0.0107 (10)
C2B0.0647 (13)0.0735 (15)0.0734 (14)0.0067 (11)0.0065 (11)0.0156 (11)
C3B0.0752 (15)0.0675 (14)0.0756 (15)0.0011 (11)0.0105 (12)0.0091 (11)
C4B0.0717 (14)0.0555 (12)0.0726 (14)0.0041 (10)0.0030 (11)0.0127 (10)
C5B0.0526 (11)0.0577 (11)0.0577 (11)0.0052 (9)0.0095 (9)0.0101 (9)
C6B0.0504 (10)0.0584 (11)0.0562 (11)0.0085 (9)0.0110 (8)0.0100 (9)
C7B0.0642 (12)0.0576 (12)0.0625 (12)0.0130 (10)0.0066 (10)0.0073 (9)
C8B0.0681 (13)0.0626 (13)0.0592 (12)0.0084 (10)0.0025 (10)0.0014 (10)
C9B0.0613 (12)0.0697 (13)0.0559 (11)0.0130 (10)0.0042 (9)0.0115 (10)
C10B0.0610 (12)0.0593 (12)0.0625 (12)0.0108 (9)0.0088 (10)0.0151 (10)
C11B0.117 (3)0.089 (2)0.135 (3)0.0251 (19)0.046 (2)0.0359 (19)
C12B0.198 (5)0.159 (4)0.140 (4)0.060 (4)0.010 (3)0.025 (3)
C13B0.0579 (12)0.0688 (13)0.0704 (14)0.0158 (10)0.0055 (10)0.0101 (11)
C14B0.0596 (12)0.0592 (12)0.0714 (13)0.0061 (10)0.0050 (10)0.0088 (10)
C15B0.0713 (15)0.0776 (16)0.104 (2)0.0190 (13)0.0036 (14)0.0193 (14)
C16B0.099 (2)0.094 (2)0.124 (3)0.0151 (17)0.029 (2)0.039 (2)
C17B0.127 (3)0.095 (2)0.090 (2)0.005 (2)0.030 (2)0.0329 (17)
C18B0.113 (2)0.0872 (19)0.0687 (16)0.0020 (17)0.0014 (15)0.0141 (14)
C19B0.0759 (15)0.0699 (14)0.0714 (14)0.0101 (12)0.0004 (12)0.0103 (11)
C20B0.0974 (19)0.0909 (19)0.0831 (17)0.0203 (15)0.0154 (15)0.0227 (14)
C21B0.134 (3)0.0674 (17)0.119 (2)0.0113 (17)0.033 (2)0.0134 (16)
Geometric parameters (Å, º) top
O1A—C13A1.222 (3)O1B—C13B1.225 (3)
O2A—C8A1.365 (3)O2B—C8B1.366 (3)
O2A—C21A1.418 (3)O2B—C21B1.412 (3)
O3A—C9A1.363 (3)O3B—C9B1.362 (3)
O3A—C20A1.419 (3)O3B—C20B1.419 (3)
C1A—C2A1.371 (3)C1B—C2B1.378 (3)
C1A—C6A1.426 (3)C1B—C6B1.429 (3)
C1A—C13A1.498 (3)C1B—C13B1.487 (3)
C2A—C3A1.402 (3)C2B—C3B1.411 (3)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.374 (3)C3B—C4B1.365 (3)
C3A—C11A1.507 (3)C3B—C11B1.541 (4)
C4A—C5A1.412 (3)C4B—C5B1.409 (3)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.417 (3)C5B—C10B1.415 (3)
C5A—C10A1.417 (3)C5B—C6B1.418 (3)
C6A—C7A1.419 (3)C6B—C7B1.420 (3)
C7A—C8A1.360 (3)C7B—C8B1.357 (3)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.425 (3)C8B—C9B1.432 (3)
C9A—C10A1.361 (3)C9B—C10B1.357 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.290 (5)C11B—C12B1.349 (5)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C13A—C14A1.493 (3)C13B—C14B1.490 (3)
C14A—C15A1.391 (3)C14B—C19B1.380 (3)
C14A—C19A1.392 (3)C14B—C15B1.392 (3)
C15A—C16A1.378 (4)C15B—C16B1.381 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.372 (4)C16B—C17B1.366 (5)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.382 (4)C17B—C18B1.362 (5)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.375 (3)C18B—C19B1.384 (4)
C18A—H18A0.9300C18B—H18B0.9300
C19A—H19A0.9300C19B—H19B0.9300
C20A—H20A0.9600C20B—H20D0.9600
C20A—H20B0.9600C20B—H20E0.9600
C20A—H20C0.9600C20B—H20F0.9600
C21A—H21A0.9600C21B—H21D0.9600
C21A—H21B0.9600C21B—H21E0.9600
C21A—H21C0.9600C21B—H21F0.9600
C8A—O2A—C21A118.0 (2)C8B—O2B—C21B117.7 (2)
C9A—O3A—C20A117.46 (18)C9B—O3B—C20B117.09 (19)
C2A—C1A—C6A119.87 (18)C2B—C1B—C6B119.9 (2)
C2A—C1A—C13A118.13 (19)C2B—C1B—C13B117.9 (2)
C6A—C1A—C13A121.81 (19)C6B—C1B—C13B122.12 (19)
C1A—C2A—C3A122.6 (2)C1B—C2B—C3B122.3 (2)
C1A—C2A—H2A118.7C1B—C2B—H2B118.8
C3A—C2A—H2A118.7C3B—C2B—H2B118.8
C4A—C3A—C2A117.7 (2)C4B—C3B—C2B117.7 (2)
C4A—C3A—C11A123.1 (2)C4B—C3B—C11B121.9 (2)
C2A—C3A—C11A119.2 (2)C2B—C3B—C11B120.4 (2)
C3A—C4A—C5A122.08 (19)C3B—C4B—C5B122.6 (2)
C3A—C4A—H4A119.0C3B—C4B—H4B118.7
C5A—C4A—H4A119.0C5B—C4B—H4B118.7
C4A—C5A—C6A119.43 (18)C4B—C5B—C10B120.8 (2)
C4A—C5A—C10A120.66 (18)C4B—C5B—C6B119.6 (2)
C6A—C5A—C10A119.92 (18)C10B—C5B—C6B119.65 (19)
C5A—C6A—C7A118.08 (18)C5B—C6B—C7B118.24 (19)
C5A—C6A—C1A118.12 (18)C5B—C6B—C1B117.91 (18)
C7A—C6A—C1A123.79 (18)C7B—C6B—C1B123.74 (19)
C8A—C7A—C6A121.1 (2)C8B—C7B—C6B121.0 (2)
C8A—C7A—H7A119.5C8B—C7B—H7B119.5
C6A—C7A—H7A119.5C6B—C7B—H7B119.5
C7A—C8A—O2A125.5 (2)C7B—C8B—O2B125.6 (2)
C7A—C8A—C9A120.6 (2)C7B—C8B—C9B120.6 (2)
O2A—C8A—C9A113.9 (2)O2B—C8B—C9B113.8 (2)
C10A—C9A—O3A125.74 (19)C10B—C9B—O3B126.2 (2)
C10A—C9A—C8A119.72 (19)C10B—C9B—C8B119.4 (2)
O3A—C9A—C8A114.54 (19)O3B—C9B—C8B114.34 (19)
C9A—C10A—C5A120.62 (19)C9B—C10B—C5B121.1 (2)
C9A—C10A—H10A119.7C9B—C10B—H10B119.5
C5A—C10A—H10A119.7C5B—C10B—H10B119.5
C12A—C11A—C3A124.0 (3)C12B—C11B—C3B114.9 (4)
C12A—C11A—H11A106.3C12B—C11B—H11C108.5
C3A—C11A—H11A106.3C3B—C11B—H11C108.5
C12A—C11A—H11B106.3C12B—C11B—H11D108.5
C3A—C11A—H11B106.3C3B—C11B—H11D108.5
H11A—C11A—H11B106.4H11C—C11B—H11D107.5
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
O1A—C13A—C14A119.39 (19)O1B—C13B—C1B121.4 (2)
O1A—C13A—C1A121.2 (2)O1B—C13B—C14B119.3 (2)
C14A—C13A—C1A119.40 (18)C1B—C13B—C14B119.27 (19)
C15A—C14A—C19A119.3 (2)C19B—C14B—C15B118.3 (2)
C15A—C14A—C13A118.4 (2)C19B—C14B—C13B122.2 (2)
C19A—C14A—C13A122.33 (19)C15B—C14B—C13B119.4 (2)
C16A—C15A—C14A119.9 (3)C16B—C15B—C14B120.3 (3)
C16A—C15A—H15A120.0C16B—C15B—H15B119.9
C14A—C15A—H15A120.0C14B—C15B—H15B119.9
C17A—C16A—C15A120.4 (3)C17B—C16B—C15B120.5 (3)
C17A—C16A—H16A119.8C17B—C16B—H16B119.8
C15A—C16A—H16A119.8C15B—C16B—H16B119.8
C16A—C17A—C18A120.1 (3)C18B—C17B—C16B119.8 (3)
C16A—C17A—H17A120.0C18B—C17B—H17B120.1
C18A—C17A—H17A120.0C16B—C17B—H17B120.1
C19A—C18A—C17A120.1 (3)C17B—C18B—C19B120.5 (3)
C19A—C18A—H18A119.9C17B—C18B—H18B119.8
C17A—C18A—H18A119.9C19B—C18B—H18B119.8
C18A—C19A—C14A120.1 (2)C14B—C19B—C18B120.6 (3)
C18A—C19A—H19A120.0C14B—C19B—H19B119.7
C14A—C19A—H19A120.0C18B—C19B—H19B119.7
O3A—C20A—H20A109.5O3B—C20B—H20D109.5
O3A—C20A—H20B109.5O3B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
O3A—C20A—H20C109.5O3B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
O2A—C21A—H21A109.5O2B—C21B—H21D109.5
O2A—C21A—H21B109.5O2B—C21B—H21E109.5
H21A—C21A—H21B109.5H21D—C21B—H21E109.5
O2A—C21A—H21C109.5O2B—C21B—H21F109.5
H21A—C21A—H21C109.5H21D—C21B—H21F109.5
H21B—C21A—H21C109.5H21E—C21B—H21F109.5

Experimental details

Crystal data
Chemical formulaC21H20O3
Mr320.37
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.9012 (2), 11.3431 (2), 16.0701 (3)
α, β, γ (°)100.170 (1), 90.487 (1), 98.373 (1)
V3)1756.46 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.12 × 0.08 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionPart of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
Tmin, Tmax0.869, 1.483
No. of measured, independent and
observed [I > 2σ(I)] reflections
33428, 7706, 4854
Rint0.034
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.214, 1.05
No. of reflections7706
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.63, 0.32

Computer programs: SMART (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

 

Acknowledgements

KS thanks the Department of Science and Technology (DST) and the Council of Scientific and Industrial Research (CSIR), India for financial support.

References

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First citationThenmozhi, S., SubbiahPandi, A., Ranjith, S., Clement, J. A. & Mohana­Krishnan, A. K. (2008). Acta Cryst. E64, o2432.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWatanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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