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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

[2-(3,4-Di­methyl­benzo­yl)phen­yl](4-meth­­oxy­phen­yl)methanone

aDepartment of Physics, Meenakshi College of Engineering, West K.K. Nagar, Chennai 600 078, India, bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 5 November 2012; accepted 20 November 2012; online 5 December 2012)

The title mol­ecule, C23H20O3, is disordered with a 180° rotation about an axis normal to the length of the mol­ecule, with the major and minor components in a 0.545 (5):0.455 (5) ratio. In the major component, the central benzene ring forms dihedral angles of 72.34 (3) and 69.46 (3)° with the dimethyl-substituted and meth­oxy-substituted benzene rings, respectively. Moreover, the central benzene ring forms dihedral angles of 50.86 (5) and 58.43 (4)° with the mean planes of the ketone groups. In the minor component, the corresponding dihedral angles between the benzene rings are 71.36 (4) and 67.94 (4)° and the dihedral angles between the benzene ring and the ketone groups are 56.44 (9) and 55.51 (8)°. In the crystal, C—H⋯O inter­actions generate a C(9) chain along the a-axis direction.

Related literature

For the uses and biological importance of diketones, see: Sugawara et al. (2001[Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.]). For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978[Hirsch, S. S. & Bailey, W. J. (1978). J. Org. Chem. 43, 4090-4094.]). For a related structure, see: Jagadeesan et al. (2011[Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20O3

  • Mr = 344.39

  • Monoclinic, C c

  • a = 21.983 (2) Å

  • b = 7.8173 (6) Å

  • c = 11.7489 (10) Å

  • β = 116.158 (2)°

  • V = 1812.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.980

  • 9619 measured reflections

  • 4759 independent reflections

  • 2728 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.173

  • S = 1.02

  • 4759 reflections

  • 388 parameters

  • 353 restraints

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C23—H23B⋯O2i 0.96 2.32 3.23 (3) 159
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The cyclic ketones play a significant role in increasing the red blood cells. They are also useful as hematopoietic agents in medicine, in particular, in the treatment of cancer, chemotherapy, radiotherapy and drug therapy (Sugawara et al., 2001). They are also important synthetic intermediates and starting materials in the synthesis of heterocyclic compounds (Hirsch & Bailey, 1978).

The molecular structure of the title compound is shown in Fig. 1. The molecule is disordered with 180° rotation about an axis normal to the length of the molecule. The unprimed atoms represent the major component where as the minor component is represented by primed ones. The site occupancy factors of the major and minor components refined to 0.545 (5) and 0.455 (5) values, respectively. The disorder prevents a discussion of accurate molecular geometry, though values are comparable to those reported in a closely related methanone derivative (Jagadeesan et al., 2011). The two overlapping molecules are shown in Fig. 2. There is a small separation between the coordinates of each pair of atoms. However, the atomic positions of all atoms in the two molecules are well resolved.

In the major component, the central benzene ring (C1–C6) forms dihedral angles of 72.34 (3) and 69.46 (3)° with the dimethyl substituted benzene ring (C8–C13) and methoxy substituted benzene ring (C17–22), respectively. Moreover, the benzene ring (C1–C6) forms dihedral angles of 50.86 (5) and 58.43 (4)° with the mean planes of the ketone groups (C1/C7/C8/O1) and (C6/C16/C17/O2), respectively. In the minor component, the central benzene ring (C1'–C6') forms dihedral angles of 71.36 (4) and 67.94 (4)° with the dimethyl substituted benzene ring (C8'–C13') and methoxy substituted benzene ring (C17'–C22'), respectively. Furthermore, the benzene ring (C1'–C6') forms dihedral angles of 56.44 (9) and 55.51 (8)° with the mean planes of the ketone groups (C1'/C7'/C8'/O1') and (C6'/C16'/C17'/O2'), respectively. The atoms C14 and O1 deviate significantly (-0.1305 (1) and -0.6096 (1) Å, respectively), from the mean plane of the benzene ring (C8–C13) and the atom O2 deviates by -0.6273 (2) Å from the mean plane of the methoxy substituted benzene ring (C17–22). On the other hand, the atom O1' deviates by -0.3678 (3) Å from the mean plane of the benzene ring (C8'–C13') and the atom O2' deviates by -0.3507 (2) Å from the mean plane of the methoxy substituted benzene ring (C17'–22').

The crystal packing is stabilized by C23–H23B···O2i intermolecular interactions (Tab. 1) generating a C(9) chain along the a axis (i: x + 1/2, y - 1/2, z + 1/2). The packing diagram of the crystal structure is shown in (Fig. 3).

Related literature top

For the uses and biological importance of diketones, see: Sugawara et al. (2001). For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978). For a related structure, see: Jagadeesan et al. (2011).

Experimental top

To a stirred suspension of [2-(3,4-dimethylbenzoyl)phenyl](4-methoxyphenyl) methanone (1 g, 3.22 mmol) in dry THF (20 ml), lead tetraaccetate (1.52 g, 3.42 mmol) was added and refluxed at 343 K for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2x20 ml), washed with brine solution and dried (Na2SO4). The removal of solvent in vacuo afforded crude product. The crude product upon crystallization from methanol furnished the tittle compound as a colorless solid.

Refinement top

The site occupancy factors of the major (unprimed atoms) and minor (primed atoms)components refined to 0.545 (5) and 0.455 (5) values, respectively. The approximate atomic positions of the disordered components were obtained from the difference electron density maps and the molecules were refined using suitable restraints. The benzene rings were refined as rigid hexagons with C–C distances 1.39 Å. The other bond-length of the major and the minor components were made similar using similarity restraints with s.u. of 0.01 Å. The atomic displacement parameters of each atom were made similar to the neighbouring atoms with suitable similarity restraints with s.u. of 0.01. Hydrogen atoms were placed in calculated positions with C–H = 0.93 and 0.96 Å for aryl and methyl type H-atoms and refined in the riding model with isotropic displacement parameters with Uiso(H) = 1.5 Ueq(methyl-C) or 1.2 Ueq(aryl-C). Due to lack of sufficient anomalous dispersion effects in diffraction measurements on the crystal, an absolute structure was not determined; 2307 Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (major component) with the atomic numbering scheme and displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The molecular structure of the title compound with the atomic numbering scheme and displacement ellipsoids at the 30% probability level. The unprimed atoms represent the major component where as the minor component is represented by primed ones.
[Figure 3] Fig. 3. The crystal packing of the title compound viewed down c axis, dashed lines indicates C–H···O interactions. H–atoms not involved in hydrogen bonds have been excluded for clarity.
[2-(3,4-Dimethylbenzoyl)phenyl](4-methoxyphenyl)methanone top
Crystal data top
C23H20O3F(000) = 728
Mr = 344.39Dx = 1.262 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 4759 reflections
a = 21.983 (2) Åθ = 2.8–29.2°
b = 7.8173 (6) ŵ = 0.08 mm1
c = 11.7489 (10) ÅT = 296 K
β = 116.158 (2)°Block, colourless
V = 1812.2 (3) Å30.35 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4759 independent reflections
Radiation source: fine-focus sealed tube2728 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 29.2°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 3030
Tmin = 0.972, Tmax = 0.980k = 810
9619 measured reflectionsl = 1616
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.073P)2 + 0.6313P]
where P = (Fo2 + 2Fc2)/3
4759 reflections(Δ/σ)max < 0.001
388 parametersΔρmax = 0.25 e Å3
353 restraintsΔρmin = 0.16 e Å3
Crystal data top
C23H20O3V = 1812.2 (3) Å3
Mr = 344.39Z = 4
Monoclinic, CcMo Kα radiation
a = 21.983 (2) ŵ = 0.08 mm1
b = 7.8173 (6) ÅT = 296 K
c = 11.7489 (10) Å0.35 × 0.30 × 0.25 mm
β = 116.158 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4759 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
2728 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.980Rint = 0.021
9619 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051353 restraints
wR(F2) = 0.173H-atom parameters constrained
S = 1.02Δρmax = 0.25 e Å3
4759 reflectionsΔρmin = 0.16 e Å3
388 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. 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*/UeqOcc. (<1)
C10.2795 (13)0.643 (2)0.395 (2)0.051 (3)0.545 (5)
C20.2648 (4)0.8003 (10)0.3360 (8)0.063 (3)0.545 (5)
H20.24070.80580.24820.076*0.545 (5)
C30.2855 (4)0.9506 (10)0.4058 (8)0.071 (3)0.545 (5)
H30.27361.05590.36500.085*0.545 (5)
C40.3239 (4)0.9437 (10)0.5365 (8)0.074 (3)0.545 (5)
H40.33771.04430.58320.089*0.545 (5)
C50.3416 (4)0.7863 (10)0.5975 (8)0.060 (2)0.545 (5)
H50.36730.78160.68500.072*0.545 (5)
C60.3209 (4)0.6359 (10)0.5277 (8)0.053 (3)0.545 (5)
C70.25776 (17)0.4651 (5)0.3147 (3)0.0453 (18)0.545 (5)
C80.18828 (17)0.4355 (5)0.2129 (3)0.0410 (15)0.545 (5)
C90.13446 (17)0.5029 (5)0.2303 (3)0.0405 (13)0.545 (5)
H90.14280.57520.29840.049*0.545 (5)
C100.06822 (17)0.4621 (5)0.1459 (3)0.0481 (16)0.545 (5)
C110.05581 (17)0.3540 (5)0.0440 (3)0.0542 (18)0.545 (5)
C120.10963 (17)0.2866 (5)0.0266 (3)0.0563 (17)0.545 (5)
H120.10130.21430.04150.068*0.545 (5)
C130.17587 (17)0.3274 (5)0.1111 (3)0.0523 (16)0.545 (5)
H130.21190.28230.09940.063*0.545 (5)
C140.0072 (3)0.5223 (14)0.1698 (8)0.084 (3)0.545 (5)
H14A0.02330.59500.24320.126*0.545 (5)
H14B0.01510.42440.18380.126*0.545 (5)
H14C0.02430.58450.09730.126*0.545 (5)
C150.0137 (4)0.3091 (12)0.0427 (7)0.061 (2)0.545 (5)
H15A0.04430.36590.01700.091*0.545 (5)
H15B0.01950.18750.04110.091*0.545 (5)
H15C0.02290.34410.12710.091*0.545 (5)
C160.3323 (3)0.4755 (8)0.5804 (6)0.062 (3)0.545 (5)
C170.4048 (3)0.4417 (8)0.6786 (6)0.052 (2)0.545 (5)
C180.4540 (3)0.5214 (8)0.6532 (6)0.073 (3)0.545 (5)
H180.44130.59450.58400.088*0.545 (5)
C190.5223 (3)0.4917 (8)0.7311 (6)0.082 (3)0.545 (5)
H190.55520.54500.71410.098*0.545 (5)
C200.5413 (3)0.3824 (8)0.8345 (6)0.099 (4)0.545 (5)
C210.4921 (3)0.3028 (8)0.8599 (6)0.097 (4)0.545 (5)
H210.50480.22970.92910.116*0.545 (5)
C220.4238 (3)0.3324 (8)0.7820 (6)0.088 (4)0.545 (5)
H220.39090.27910.79900.105*0.545 (5)
C230.6593 (4)0.3804 (18)0.9282 (15)0.189 (7)0.545 (5)
H23A0.65660.36480.84500.284*0.545 (5)
H23B0.69760.31880.98900.284*0.545 (5)
H23C0.66430.49980.94920.284*0.545 (5)
O10.3020 (6)0.3679 (13)0.3246 (14)0.058 (3)0.545 (5)
O20.2898 (11)0.365 (3)0.566 (2)0.064 (4)0.545 (5)
O30.6019 (4)0.3206 (15)0.9301 (9)0.153 (4)0.545 (5)
C1'0.3153 (7)0.6357 (14)0.5030 (13)0.054 (3)0.455 (5)
C2'0.3332 (8)0.795 (2)0.5636 (13)0.073 (4)0.455 (5)
H2'0.36120.79940.65030.087*0.455 (5)
C3'0.3099 (7)0.945 (2)0.4963 (14)0.087 (4)0.455 (5)
H3'0.32051.05140.53520.104*0.455 (5)
C4'0.2702 (8)0.927 (2)0.3688 (15)0.082 (4)0.455 (5)
H4'0.25681.02510.31960.099*0.455 (5)
C5'0.2495 (8)0.776 (2)0.3109 (13)0.073 (3)0.455 (5)
H5'0.21740.77310.22650.088*0.455 (5)
C6'0.2754 (15)0.626 (2)0.375 (2)0.053 (3)0.455 (5)
C7'0.3402 (3)0.4675 (9)0.5975 (6)0.047 (2)0.455 (5)
C8'0.4154 (3)0.4348 (9)0.6869 (6)0.061 (3)0.455 (5)
C9'0.4712 (3)0.4976 (9)0.6739 (6)0.0469 (19)0.455 (5)
H9'0.46490.56770.60560.056*0.455 (5)
C10'0.5363 (3)0.4558 (9)0.7629 (6)0.0415 (18)0.455 (5)
C11'0.5457 (3)0.3511 (9)0.8650 (6)0.0474 (19)0.455 (5)
C12'0.4900 (3)0.2882 (9)0.8780 (6)0.073 (3)0.455 (5)
H12'0.49630.21820.94630.088*0.455 (5)
C13'0.4248 (3)0.3301 (9)0.7889 (6)0.067 (3)0.455 (5)
H13'0.38750.28800.79760.080*0.455 (5)
C14'0.5888 (3)0.5345 (13)0.7310 (8)0.064 (2)0.455 (5)
H14D0.63310.50340.79420.096*0.455 (5)
H14E0.58420.65670.72860.096*0.455 (5)
H14F0.58290.49390.64960.096*0.455 (5)
C15'0.6212 (5)0.318 (2)0.9610 (10)0.075 (3)0.455 (5)
H15D0.65050.37500.93210.112*0.455 (5)
H15E0.63020.19760.96720.112*0.455 (5)
H15F0.62930.36201.04280.112*0.455 (5)
C16'0.2607 (3)0.4816 (7)0.3035 (5)0.055 (2)0.455 (5)
C17'0.1879 (3)0.4505 (7)0.2433 (5)0.061 (2)0.455 (5)
C18'0.1400 (3)0.5283 (7)0.2734 (5)0.086 (3)0.455 (5)
H18'0.15390.59780.34470.103*0.455 (5)
C19'0.0713 (3)0.5023 (7)0.1969 (5)0.088 (3)0.455 (5)
H19'0.03930.55440.21700.105*0.455 (5)
C20'0.0505 (3)0.3985 (7)0.0903 (5)0.067 (2)0.455 (5)
C21'0.0984 (3)0.3206 (7)0.0602 (5)0.072 (3)0.455 (5)
H21'0.08450.25120.01110.086*0.455 (5)
C22'0.1671 (3)0.3466 (7)0.1367 (5)0.070 (2)0.455 (5)
H22'0.19920.29460.11660.084*0.455 (5)
C23'0.0429 (8)0.293 (2)0.0741 (13)0.147 (7)0.455 (5)
H23D0.04730.36390.14410.220*0.455 (5)
H23E0.08610.24330.09160.220*0.455 (5)
H23F0.01060.20400.06200.220*0.455 (5)
O1'0.2947 (14)0.375 (4)0.593 (3)0.061 (4)0.455 (5)
O2'0.3057 (9)0.378 (2)0.322 (3)0.097 (5)0.455 (5)
O3'0.0204 (3)0.3942 (8)0.0374 (6)0.0958 (19)0.455 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.049 (5)0.035 (4)0.066 (6)0.004 (3)0.023 (4)0.009 (3)
C20.060 (5)0.038 (4)0.079 (6)0.009 (4)0.018 (4)0.004 (4)
C30.071 (6)0.026 (3)0.096 (7)0.004 (4)0.019 (5)0.004 (5)
C40.072 (6)0.035 (4)0.089 (7)0.002 (4)0.012 (5)0.006 (4)
C50.065 (5)0.037 (4)0.073 (5)0.006 (3)0.027 (4)0.010 (4)
C60.059 (4)0.048 (5)0.056 (4)0.005 (3)0.028 (4)0.002 (3)
C70.050 (4)0.030 (3)0.055 (4)0.005 (3)0.022 (3)0.005 (3)
C80.048 (3)0.037 (3)0.040 (3)0.010 (3)0.021 (2)0.002 (2)
C90.040 (3)0.043 (3)0.039 (3)0.006 (2)0.018 (2)0.002 (2)
C100.063 (4)0.041 (3)0.042 (3)0.002 (3)0.025 (3)0.006 (3)
C110.074 (4)0.040 (3)0.053 (4)0.010 (3)0.032 (3)0.002 (3)
C120.077 (4)0.053 (4)0.056 (3)0.013 (3)0.045 (3)0.018 (3)
C130.069 (4)0.038 (3)0.069 (4)0.004 (3)0.047 (3)0.015 (3)
C140.068 (5)0.081 (6)0.092 (6)0.007 (4)0.026 (4)0.004 (5)
C150.076 (5)0.054 (4)0.055 (4)0.007 (4)0.031 (4)0.013 (3)
C160.049 (4)0.057 (5)0.064 (4)0.008 (4)0.011 (3)0.003 (4)
C170.041 (3)0.047 (4)0.068 (5)0.012 (3)0.025 (3)0.009 (4)
C180.033 (3)0.071 (5)0.102 (5)0.011 (3)0.018 (3)0.021 (4)
C190.034 (3)0.080 (6)0.110 (6)0.004 (4)0.013 (4)0.017 (5)
C200.052 (4)0.081 (6)0.119 (6)0.019 (4)0.003 (4)0.025 (5)
C210.088 (6)0.069 (6)0.096 (6)0.032 (5)0.006 (5)0.013 (5)
C220.069 (6)0.074 (6)0.089 (6)0.028 (5)0.007 (5)0.005 (6)
C230.067 (5)0.186 (11)0.219 (12)0.027 (7)0.025 (7)0.041 (10)
O10.056 (5)0.037 (3)0.064 (5)0.007 (3)0.011 (4)0.009 (3)
O20.057 (5)0.051 (5)0.069 (10)0.009 (3)0.014 (6)0.002 (5)
O30.088 (5)0.135 (6)0.160 (7)0.023 (5)0.014 (5)0.061 (5)
C1'0.064 (5)0.036 (5)0.066 (5)0.008 (4)0.031 (4)0.009 (3)
C2'0.073 (6)0.063 (7)0.061 (6)0.010 (5)0.009 (5)0.005 (5)
C3'0.079 (7)0.050 (6)0.085 (7)0.004 (5)0.006 (6)0.011 (5)
C4'0.080 (7)0.051 (6)0.090 (7)0.005 (5)0.015 (5)0.002 (5)
C5'0.068 (6)0.054 (5)0.070 (6)0.019 (4)0.006 (4)0.004 (4)
C6'0.041 (5)0.046 (5)0.068 (7)0.002 (4)0.021 (5)0.001 (4)
C7'0.068 (5)0.040 (5)0.044 (4)0.002 (4)0.035 (3)0.005 (3)
C8'0.057 (4)0.057 (5)0.065 (5)0.004 (4)0.025 (4)0.009 (5)
C9'0.047 (4)0.042 (4)0.050 (4)0.007 (3)0.020 (3)0.004 (3)
C10'0.033 (3)0.038 (4)0.050 (4)0.009 (3)0.016 (3)0.002 (3)
C11'0.054 (4)0.048 (4)0.043 (4)0.008 (3)0.024 (3)0.003 (3)
C12'0.079 (6)0.075 (6)0.069 (5)0.005 (5)0.037 (5)0.010 (5)
C13'0.061 (6)0.081 (7)0.068 (6)0.003 (5)0.038 (5)0.002 (6)
C14'0.050 (4)0.066 (6)0.088 (6)0.009 (4)0.042 (4)0.002 (5)
C15'0.061 (6)0.100 (7)0.049 (5)0.036 (5)0.012 (4)0.001 (5)
C16'0.041 (4)0.055 (5)0.072 (5)0.006 (4)0.029 (4)0.018 (4)
C17'0.061 (5)0.063 (4)0.052 (4)0.001 (4)0.017 (3)0.002 (3)
C18'0.064 (5)0.085 (6)0.101 (6)0.008 (4)0.030 (4)0.002 (5)
C19'0.071 (5)0.087 (6)0.111 (6)0.002 (4)0.047 (4)0.015 (5)
C20'0.047 (3)0.061 (5)0.085 (5)0.006 (4)0.021 (4)0.015 (4)
C21'0.073 (5)0.065 (5)0.061 (4)0.003 (4)0.014 (4)0.000 (4)
C22'0.067 (4)0.073 (5)0.070 (4)0.010 (4)0.029 (4)0.006 (4)
C23'0.110 (11)0.137 (11)0.118 (10)0.048 (9)0.018 (7)0.033 (8)
O1'0.058 (5)0.063 (6)0.055 (8)0.023 (4)0.017 (5)0.003 (5)
O2'0.067 (7)0.107 (9)0.127 (10)0.016 (7)0.053 (7)0.011 (8)
O3'0.092 (4)0.093 (4)0.093 (4)0.014 (3)0.032 (3)0.012 (3)
Geometric parameters (Å, º) top
C1—C21.38 (2)C1'—C6'1.37 (2)
C1—C61.42 (2)C1'—C2'1.401 (15)
C1—C71.628 (10)C1'—C7'1.651 (11)
C2—C31.3900C2'—C3'1.380 (16)
C2—H20.9300C2'—H2'0.9300
C3—C41.3900C3'—C4'1.369 (13)
C3—H30.9300C3'—H3'0.9300
C4—C51.3901C4'—C5'1.333 (16)
C4—H40.9300C4'—H4'0.9300
C5—C61.3900C5'—C6'1.38 (3)
C5—H50.9300C5'—H5'0.9300
C6—C161.372 (9)C6'—C16'1.355 (12)
C7—O11.198 (11)C7'—O1'1.212 (15)
C7—C81.4856C7'—C8'1.5405
C8—C91.3900C8'—C9'1.3899
C8—C131.3900C8'—C13'1.3901
C9—C101.3900C9'—C10'1.3901
C9—H90.9300C9'—H9'0.9300
C10—C111.3901C10'—C11'1.3900
C10—C141.561 (7)C10'—C14'1.495 (7)
C11—C121.3900C11'—C12'1.3901
C11—C151.457 (7)C11'—C15'1.563 (8)
C12—C131.3900C12'—C13'1.3899
C12—H120.9300C12'—H12'0.9300
C13—H130.9300C13'—H13'0.9300
C14—H14A0.9600C14'—H14D0.9600
C14—H14B0.9600C14'—H14E0.9600
C14—H14C0.9600C14'—H14F0.9600
C15—H15A0.9600C15'—H15D0.9600
C15—H15B0.9600C15'—H15E0.9600
C15—H15C0.9600C15'—H15F0.9600
C16—O21.231 (14)C16'—O2'1.220 (15)
C16—C171.5239C16'—C17'1.4562
C17—C181.3899C17'—C18'1.3899
C17—C221.3900C17'—C22'1.3901
C18—C191.3901C18'—C19'1.3900
C18—H180.9300C18'—H18'0.9300
C19—C201.3900C19'—C20'1.3900
C19—H190.9300C19'—H19'0.9300
C20—C211.3902C20'—C21'1.3901
C20—O31.396 (7)C20'—O3'1.402 (7)
C21—C221.3899C21'—C22'1.3900
C21—H210.9300C21'—H21'0.9300
C22—H220.9300C22'—H22'0.9300
C23—O31.355 (9)C23'—O3'1.418 (10)
C23—H23A0.9600C23'—H23D0.9600
C23—H23B0.9600C23'—H23E0.9600
C23—H23C0.9600C23'—H23F0.9600
C2—C1—C6118.8 (10)C3'—C2'—C1'120.9 (10)
C2—C1—C7121.6 (13)C3'—C2'—H2'119.6
C6—C1—C7119.3 (14)C1'—C2'—H2'119.6
C1—C2—C3120.9 (6)C4'—C3'—C2'115.8 (14)
C1—C2—H2119.5C4'—C3'—H3'122.1
C3—C2—H2119.5C2'—C3'—H3'122.1
C2—C3—C4120.0C5'—C4'—C3'124.0 (15)
C2—C3—H3120.0C5'—C4'—H4'118.0
C4—C3—H3120.0C3'—C4'—H4'118.0
C3—C4—C5120.0C4'—C5'—C6'120.6 (12)
C3—C4—H4120.0C4'—C5'—H5'119.7
C5—C4—H4120.0C6'—C5'—H5'119.7
C6—C5—C4120.0C16'—C6'—C1'126 (2)
C6—C5—H5120.0C16'—C6'—C5'116.3 (17)
C4—C5—H5120.0C1'—C6'—C5'117.4 (14)
C16—C6—C5124.0 (5)O1'—C7'—C8'123.2 (16)
C16—C6—C1115.5 (9)O1'—C7'—C1'114.9 (17)
C5—C6—C1120.1 (7)C8'—C7'—C1'121.9 (5)
O1—C7—C8118.8 (5)C9'—C8'—C13'120.0
O1—C7—C1117.8 (11)C9'—C8'—C7'126.9
C8—C7—C1122.4 (9)C13'—C8'—C7'113.1
C9—C8—C13120.0C8'—C9'—C10'120.0
C9—C8—C7117.5C8'—C9'—H9'120.0
C13—C8—C7122.0C10'—C9'—H9'120.0
C8—C9—C10120.0C11'—C10'—C9'120.0
C8—C9—H9120.0C11'—C10'—C14'128.4 (4)
C10—C9—H9120.0C9'—C10'—C14'111.6 (4)
C9—C10—C11120.0C10'—C11'—C12'120.0
C9—C10—C14121.1 (4)C10'—C11'—C15'115.2 (5)
C11—C10—C14118.7 (4)C12'—C11'—C15'124.7 (5)
C12—C11—C10120.0C13'—C12'—C11'120.0
C12—C11—C15120.2 (3)C13'—C12'—H12'120.0
C10—C11—C15119.7 (3)C11'—C12'—H12'120.0
C11—C12—C13120.0C12'—C13'—C8'120.0
C11—C12—H12120.0C12'—C13'—H13'120.0
C13—C12—H12120.0C8'—C13'—H13'120.0
C12—C13—C8120.0C10'—C14'—H14D109.5
C12—C13—H13120.0C10'—C14'—H14E109.5
C8—C13—H13120.0H14D—C14'—H14E109.5
C10—C14—H14A109.5C10'—C14'—H14F109.5
C10—C14—H14B109.5H14D—C14'—H14F109.5
H14A—C14—H14B109.5H14E—C14'—H14F109.5
C10—C14—H14C109.5C11'—C15'—H15D109.5
H14A—C14—H14C109.5C11'—C15'—H15E109.5
H14B—C14—H14C109.5H15D—C15'—H15E109.5
C11—C15—H15A109.5C11'—C15'—H15F109.5
C11—C15—H15B109.5H15D—C15'—H15F109.5
H15A—C15—H15B109.5H15E—C15'—H15F109.5
C11—C15—H15C109.5O2'—C16'—C6'119.0 (16)
H15A—C15—H15C109.5O2'—C16'—C17'127.4 (10)
H15B—C15—H15C109.5C6'—C16'—C17'110.5 (14)
O2—C16—C6127.3 (14)C18'—C17'—C22'120.0
O2—C16—C17117.3 (12)C18'—C17'—C16'126.6
C6—C16—C17114.9 (4)C22'—C17'—C16'112.9
C18—C17—C22120.0C17'—C18'—C19'120.0
C18—C17—C16114.4C17'—C18'—H18'120.0
C22—C17—C16125.4C19'—C18'—H18'120.0
C17—C18—C19120.0C20'—C19'—C18'120.0
C17—C18—H18120.0C20'—C19'—H19'120.0
C19—C18—H18120.0C18'—C19'—H19'120.0
C20—C19—C18120.0C19'—C20'—C21'120.0
C20—C19—H19120.0C19'—C20'—O3'105.9 (3)
C18—C19—H19120.0C21'—C20'—O3'134.1 (3)
C19—C20—C21120.0C22'—C21'—C20'120.0
C19—C20—O3136.8 (6)C22'—C21'—H21'120.0
C21—C20—O3103.2 (6)C20'—C21'—H21'120.0
C22—C21—C20120.0C21'—C22'—C17'120.0
C22—C21—H21120.0C21'—C22'—H22'120.0
C20—C21—H21120.0C17'—C22'—H22'120.0
C21—C22—C17120.0O3'—C23'—H23D109.5
C21—C22—H22120.0O3'—C23'—H23E109.5
C17—C22—H22120.0H23D—C23'—H23E109.5
C23—O3—C20115.6 (9)O3'—C23'—H23F109.5
C6'—C1'—C2'120.6 (12)H23D—C23'—H23F109.5
C6'—C1'—C7'123.7 (13)H23E—C23'—H23F109.5
C2'—C1'—C7'115.5 (10)C20'—O3'—C23'106.9 (8)
C6—C1—C2—C35 (3)C6'—C1'—C2'—C3'1 (2)
C7—C1—C2—C3178.1 (13)C7'—C1'—C2'—C3'173.8 (12)
C1—C2—C3—C42.6 (14)C1'—C2'—C3'—C4'1.4 (17)
C2—C3—C4—C50.0C2'—C3'—C4'—C5'5.3 (15)
C3—C4—C5—C60.0C3'—C4'—C5'—C6'9 (3)
C4—C5—C6—C16175.7 (6)C2'—C1'—C6'—C16'172 (2)
C4—C5—C6—C12.5 (14)C7'—C1'—C6'—C16'13 (4)
C2—C1—C6—C16178.8 (16)C2'—C1'—C6'—C5'5 (3)
C7—C1—C6—C168 (3)C7'—C1'—C6'—C5'169.8 (17)
C2—C1—C6—C55 (3)C4'—C5'—C6'—C16'168.9 (19)
C7—C1—C6—C5178.2 (12)C4'—C5'—C6'—C1'9 (4)
C2—C1—C7—O1119 (2)C6'—C1'—C7'—O1'55 (3)
C6—C1—C7—O154 (3)C2'—C1'—C7'—O1'120.1 (19)
C2—C1—C7—C849 (3)C6'—C1'—C7'—C8'126.6 (18)
C6—C1—C7—C8138.5 (15)C2'—C1'—C7'—C8'58.3 (9)
O1—C7—C8—C9156.0 (9)O1'—C7'—C8'—C9'159.0 (19)
C1—C7—C8—C936.2 (12)C1'—C7'—C8'—C9'22.7 (7)
O1—C7—C8—C1316.1 (9)O1'—C7'—C8'—C13'20.8 (19)
C1—C7—C8—C13151.7 (12)C1'—C7'—C8'—C13'157.4 (7)
C13—C8—C9—C100.0C13'—C8'—C9'—C10'0.0
C7—C8—C9—C10172.3C7'—C8'—C9'—C10'179.8
C8—C9—C10—C110.0C8'—C9'—C10'—C11'0.0
C8—C9—C10—C14174.4 (5)C8'—C9'—C10'—C14'179.4 (5)
C9—C10—C11—C120.0C9'—C10'—C11'—C12'0.0
C14—C10—C11—C12174.5 (5)C14'—C10'—C11'—C12'179.3 (6)
C9—C10—C11—C15178.8 (5)C9'—C10'—C11'—C15'178.0 (8)
C14—C10—C11—C154.3 (6)C14'—C10'—C11'—C15'2.7 (8)
C10—C11—C12—C130.0C10'—C11'—C12'—C13'0.0
C15—C11—C12—C13178.8 (5)C15'—C11'—C12'—C13'177.8 (8)
C11—C12—C13—C80.0C11'—C12'—C13'—C8'0.0
C9—C8—C13—C120.0C9'—C8'—C13'—C12'0.0
C7—C8—C13—C12171.9C7'—C8'—C13'—C12'179.8
C5—C6—C16—O2124.1 (16)C1'—C6'—C16'—O2'42 (4)
C1—C6—C16—O249 (2)C5'—C6'—C16'—O2'135 (2)
C5—C6—C16—C1748.6 (6)C1'—C6'—C16'—C17'119 (3)
C1—C6—C16—C17138.0 (13)C5'—C6'—C16'—C17'63 (3)
O2—C16—C17—C18151.6 (14)O2'—C16'—C17'—C18'145.8 (17)
C6—C16—C17—C1835.0 (6)C6'—C16'—C17'—C18'14.0 (14)
O2—C16—C17—C2223.9 (14)O2'—C16'—C17'—C22'42.1 (17)
C6—C16—C17—C22149.5 (6)C6'—C16'—C17'—C22'158.1 (14)
C22—C17—C18—C190.0C22'—C17'—C18'—C19'0.0
C16—C17—C18—C19175.8C16'—C17'—C18'—C19'171.6
C17—C18—C19—C200.0C17'—C18'—C19'—C20'0.0
C18—C19—C20—C210.0C18'—C19'—C20'—C21'0.0
C18—C19—C20—O3179.0 (8)C18'—C19'—C20'—O3'178.0 (4)
C19—C20—C21—C220.0C19'—C20'—C21'—C22'0.0
O3—C20—C21—C22179.3 (6)O3'—C20'—C21'—C22'177.4 (5)
C20—C21—C22—C170.0C20'—C21'—C22'—C17'0.0
C18—C17—C22—C210.0C18'—C17'—C22'—C21'0.0
C16—C17—C22—C21175.3C16'—C17'—C22'—C21'172.7
C19—C20—O3—C231.4 (15)C19'—C20'—O3'—C23'178.1 (8)
C21—C20—O3—C23179.5 (10)C21'—C20'—O3'—C23'4.2 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23B···O2i0.962.323.23 (3)159
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H20O3
Mr344.39
Crystal system, space groupMonoclinic, Cc
Temperature (K)296
a, b, c (Å)21.983 (2), 7.8173 (6), 11.7489 (10)
β (°) 116.158 (2)
V3)1812.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.972, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
9619, 4759, 2728
Rint0.021
(sin θ/λ)max1)0.686
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.173, 1.02
No. of reflections4759
No. of parameters388
No. of restraints353
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.16

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23B···O2i0.962.323.23 (3)159
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationHirsch, S. S. & Bailey, W. J. (1978). J. Org. Chem. 43, 4090–4094.  CrossRef CAS Web of Science
First citationJagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.

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