[2-(3,4-Dimethyl-benzo-yl)phen-yl](4-meth-oxy-phen-yl)methanone.

The title mol-ecule, C23H20O3, is disordered with a 180° rotation about an axis normal to the length of the mol-ecule, 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 meth-oxy-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 inter-actions 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 ▶). For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978 ▶). For a related structure, see: Jagadeesan et al. (2011 ▶).

Experimental

Crystal data

C23H20O3

M = 344.39

Monoclinic,

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 ▶) T min = 0.972, T max = 0.980

9619 measured reflections

4759 independent reflections

2728 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047654/pv2606sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047654/pv2606Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047654/pv2606Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H20O3	F(000) = 728
Mr = 344.39	Dx = 1.262 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4759 reflections
a = 21.983 (2) Å	θ = 2.8–29.2°
b = 7.8173 (6) Å	µ = 0.08 mm−1
c = 11.7489 (10) Å	T = 296 K
β = 116.158 (2)°	Block, colourless
V = 1812.2 (3) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4759 independent reflections
Radiation source: fine-focus sealed tube	2728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 29.2°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −30→30
Tmin = 0.972, Tmax = 0.980	k = −8→10
9619 measured reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-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 parameters	Δρmax = 0.25 e Å−3
353 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2795 (13)	0.643 (2)	0.395 (2)	0.051 (3)	0.545 (5)
C2	0.2648 (4)	0.8003 (10)	0.3360 (8)	0.063 (3)	0.545 (5)
H2	0.2407	0.8058	0.2482	0.076*	0.545 (5)
C3	0.2855 (4)	0.9506 (10)	0.4058 (8)	0.071 (3)	0.545 (5)
H3	0.2736	1.0559	0.3650	0.085*	0.545 (5)
C4	0.3239 (4)	0.9437 (10)	0.5365 (8)	0.074 (3)	0.545 (5)
H4	0.3377	1.0443	0.5832	0.089*	0.545 (5)
C5	0.3416 (4)	0.7863 (10)	0.5975 (8)	0.060 (2)	0.545 (5)
H5	0.3673	0.7816	0.6850	0.072*	0.545 (5)
C6	0.3209 (4)	0.6359 (10)	0.5277 (8)	0.053 (3)	0.545 (5)
C7	0.25776 (17)	0.4651 (5)	0.3147 (3)	0.0453 (18)	0.545 (5)
C8	0.18828 (17)	0.4355 (5)	0.2129 (3)	0.0410 (15)	0.545 (5)
C9	0.13446 (17)	0.5029 (5)	0.2303 (3)	0.0405 (13)	0.545 (5)
H9	0.1428	0.5752	0.2984	0.049*	0.545 (5)
C10	0.06822 (17)	0.4621 (5)	0.1459 (3)	0.0481 (16)	0.545 (5)
C11	0.05581 (17)	0.3540 (5)	0.0440 (3)	0.0542 (18)	0.545 (5)
C12	0.10963 (17)	0.2866 (5)	0.0266 (3)	0.0563 (17)	0.545 (5)
H12	0.1013	0.2143	−0.0415	0.068*	0.545 (5)
C13	0.17587 (17)	0.3274 (5)	0.1111 (3)	0.0523 (16)	0.545 (5)
H13	0.2119	0.2823	0.0994	0.063*	0.545 (5)
C14	0.0072 (3)	0.5223 (14)	0.1698 (8)	0.084 (3)	0.545 (5)
H14A	0.0233	0.5950	0.2432	0.126*	0.545 (5)
H14B	−0.0151	0.4244	0.1838	0.126*	0.545 (5)
H14C	−0.0243	0.5845	0.0973	0.126*	0.545 (5)
C15	−0.0137 (4)	0.3091 (12)	−0.0427 (7)	0.061 (2)	0.545 (5)
H15A	−0.0443	0.3659	−0.0170	0.091*	0.545 (5)
H15B	−0.0195	0.1875	−0.0411	0.091*	0.545 (5)
H15C	−0.0229	0.3441	−0.1271	0.091*	0.545 (5)
C16	0.3323 (3)	0.4755 (8)	0.5804 (6)	0.062 (3)	0.545 (5)
C17	0.4048 (3)	0.4417 (8)	0.6786 (6)	0.052 (2)	0.545 (5)
C18	0.4540 (3)	0.5214 (8)	0.6532 (6)	0.073 (3)	0.545 (5)
H18	0.4413	0.5945	0.5840	0.088*	0.545 (5)
C19	0.5223 (3)	0.4917 (8)	0.7311 (6)	0.082 (3)	0.545 (5)
H19	0.5552	0.5450	0.7141	0.098*	0.545 (5)
C20	0.5413 (3)	0.3824 (8)	0.8345 (6)	0.099 (4)	0.545 (5)
C21	0.4921 (3)	0.3028 (8)	0.8599 (6)	0.097 (4)	0.545 (5)
H21	0.5048	0.2297	0.9291	0.116*	0.545 (5)
C22	0.4238 (3)	0.3324 (8)	0.7820 (6)	0.088 (4)	0.545 (5)
H22	0.3909	0.2791	0.7990	0.105*	0.545 (5)
C23	0.6593 (4)	0.3804 (18)	0.9282 (15)	0.189 (7)	0.545 (5)
H23A	0.6566	0.3648	0.8450	0.284*	0.545 (5)
H23B	0.6976	0.3188	0.9890	0.284*	0.545 (5)
H23C	0.6643	0.4998	0.9492	0.284*	0.545 (5)
O1	0.3020 (6)	0.3679 (13)	0.3246 (14)	0.058 (3)	0.545 (5)
O2	0.2898 (11)	0.365 (3)	0.566 (2)	0.064 (4)	0.545 (5)
O3	0.6019 (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'	0.3612	0.7994	0.6503	0.087*	0.455 (5)
C3'	0.3099 (7)	0.945 (2)	0.4963 (14)	0.087 (4)	0.455 (5)
H3'	0.3205	1.0514	0.5352	0.104*	0.455 (5)
C4'	0.2702 (8)	0.927 (2)	0.3688 (15)	0.082 (4)	0.455 (5)
H4'	0.2568	1.0251	0.3196	0.099*	0.455 (5)
C5'	0.2495 (8)	0.776 (2)	0.3109 (13)	0.073 (3)	0.455 (5)
H5'	0.2174	0.7731	0.2265	0.088*	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'	0.4649	0.5677	0.6056	0.056*	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'	0.4963	0.2182	0.9463	0.088*	0.455 (5)
C13'	0.4248 (3)	0.3301 (9)	0.7889 (6)	0.067 (3)	0.455 (5)
H13'	0.3875	0.2880	0.7976	0.080*	0.455 (5)
C14'	0.5888 (3)	0.5345 (13)	0.7310 (8)	0.064 (2)	0.455 (5)
H14D	0.6331	0.5034	0.7942	0.096*	0.455 (5)
H14E	0.5842	0.6567	0.7286	0.096*	0.455 (5)
H14F	0.5829	0.4939	0.6496	0.096*	0.455 (5)
C15'	0.6212 (5)	0.318 (2)	0.9610 (10)	0.075 (3)	0.455 (5)
H15D	0.6505	0.3750	0.9321	0.112*	0.455 (5)
H15E	0.6302	0.1976	0.9672	0.112*	0.455 (5)
H15F	0.6293	0.3620	1.0428	0.112*	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'	0.1539	0.5978	0.3447	0.103*	0.455 (5)
C19'	0.0713 (3)	0.5023 (7)	0.1969 (5)	0.088 (3)	0.455 (5)
H19'	0.0393	0.5544	0.2170	0.105*	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'	0.0845	0.2512	−0.0111	0.086*	0.455 (5)
C22'	0.1671 (3)	0.3466 (7)	0.1367 (5)	0.070 (2)	0.455 (5)
H22'	0.1992	0.2946	0.1166	0.084*	0.455 (5)
C23'	−0.0429 (8)	0.293 (2)	−0.0741 (13)	0.147 (7)	0.455 (5)
H23D	−0.0473	0.3639	−0.1441	0.220*	0.455 (5)
H23E	−0.0861	0.2433	−0.0916	0.220*	0.455 (5)
H23F	−0.0106	0.2040	−0.0620	0.220*	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)

	U11	U22	U33	U12	U13	U23
C1	0.049 (5)	0.035 (4)	0.066 (6)	0.004 (3)	0.023 (4)	−0.009 (3)
C2	0.060 (5)	0.038 (4)	0.079 (6)	−0.009 (4)	0.018 (4)	0.004 (4)
C3	0.071 (6)	0.026 (3)	0.096 (7)	−0.004 (4)	0.019 (5)	0.004 (5)
C4	0.072 (6)	0.035 (4)	0.089 (7)	−0.002 (4)	0.012 (5)	−0.006 (4)
C5	0.065 (5)	0.037 (4)	0.073 (5)	−0.006 (3)	0.027 (4)	−0.010 (4)
C6	0.059 (4)	0.048 (5)	0.056 (4)	−0.005 (3)	0.028 (4)	−0.002 (3)
C7	0.050 (4)	0.030 (3)	0.055 (4)	0.005 (3)	0.022 (3)	0.005 (3)
C8	0.048 (3)	0.037 (3)	0.040 (3)	0.010 (3)	0.021 (2)	0.002 (2)
C9	0.040 (3)	0.043 (3)	0.039 (3)	0.006 (2)	0.018 (2)	0.002 (2)
C10	0.063 (4)	0.041 (3)	0.042 (3)	0.002 (3)	0.025 (3)	−0.006 (3)
C11	0.074 (4)	0.040 (3)	0.053 (4)	0.010 (3)	0.032 (3)	−0.002 (3)
C12	0.077 (4)	0.053 (4)	0.056 (3)	−0.013 (3)	0.045 (3)	−0.018 (3)
C13	0.069 (4)	0.038 (3)	0.069 (4)	−0.004 (3)	0.047 (3)	−0.015 (3)
C14	0.068 (5)	0.081 (6)	0.092 (6)	0.007 (4)	0.026 (4)	−0.004 (5)
C15	0.076 (5)	0.054 (4)	0.055 (4)	−0.007 (4)	0.031 (4)	−0.013 (3)
C16	0.049 (4)	0.057 (5)	0.064 (4)	0.008 (4)	0.011 (3)	−0.003 (4)
C17	0.041 (3)	0.047 (4)	0.068 (5)	0.012 (3)	0.025 (3)	−0.009 (4)
C18	0.033 (3)	0.071 (5)	0.102 (5)	0.011 (3)	0.018 (3)	−0.021 (4)
C19	0.034 (3)	0.080 (6)	0.110 (6)	0.004 (4)	0.013 (4)	−0.017 (5)
C20	0.052 (4)	0.081 (6)	0.119 (6)	0.019 (4)	−0.003 (4)	−0.025 (5)
C21	0.088 (6)	0.069 (6)	0.096 (6)	0.032 (5)	0.006 (5)	0.013 (5)
C22	0.069 (6)	0.074 (6)	0.089 (6)	0.028 (5)	0.007 (5)	0.005 (6)
C23	0.067 (5)	0.186 (11)	0.219 (12)	0.027 (7)	−0.025 (7)	−0.041 (10)
O1	0.056 (5)	0.037 (3)	0.064 (5)	0.007 (3)	0.011 (4)	−0.009 (3)
O2	0.057 (5)	0.051 (5)	0.069 (10)	−0.009 (3)	0.014 (6)	0.002 (5)
O3	0.088 (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)

C1—C2	1.38 (2)	C1'—C6'	1.37 (2)
C1—C6	1.42 (2)	C1'—C2'	1.401 (15)
C1—C7	1.628 (10)	C1'—C7'	1.651 (11)
C2—C3	1.3900	C2'—C3'	1.380 (16)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.3900	C3'—C4'	1.369 (13)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.3901	C4'—C5'	1.333 (16)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.3900	C5'—C6'	1.38 (3)
C5—H5	0.9300	C5'—H5'	0.9300
C6—C16	1.372 (9)	C6'—C16'	1.355 (12)
C7—O1	1.198 (11)	C7'—O1'	1.212 (15)
C7—C8	1.4856	C7'—C8'	1.5405
C8—C9	1.3900	C8'—C9'	1.3899
C8—C13	1.3900	C8'—C13'	1.3901
C9—C10	1.3900	C9'—C10'	1.3901
C9—H9	0.9300	C9'—H9'	0.9300
C10—C11	1.3901	C10'—C11'	1.3900
C10—C14	1.561 (7)	C10'—C14'	1.495 (7)
C11—C12	1.3900	C11'—C12'	1.3901
C11—C15	1.457 (7)	C11'—C15'	1.563 (8)
C12—C13	1.3900	C12'—C13'	1.3899
C12—H12	0.9300	C12'—H12'	0.9300
C13—H13	0.9300	C13'—H13'	0.9300
C14—H14A	0.9600	C14'—H14D	0.9600
C14—H14B	0.9600	C14'—H14E	0.9600
C14—H14C	0.9600	C14'—H14F	0.9600
C15—H15A	0.9600	C15'—H15D	0.9600
C15—H15B	0.9600	C15'—H15E	0.9600
C15—H15C	0.9600	C15'—H15F	0.9600
C16—O2	1.231 (14)	C16'—O2'	1.220 (15)
C16—C17	1.5239	C16'—C17'	1.4562
C17—C18	1.3899	C17'—C18'	1.3899
C17—C22	1.3900	C17'—C22'	1.3901
C18—C19	1.3901	C18'—C19'	1.3900
C18—H18	0.9300	C18'—H18'	0.9300
C19—C20	1.3900	C19'—C20'	1.3900
C19—H19	0.9300	C19'—H19'	0.9300
C20—C21	1.3902	C20'—C21'	1.3901
C20—O3	1.396 (7)	C20'—O3'	1.402 (7)
C21—C22	1.3899	C21'—C22'	1.3900
C21—H21	0.9300	C21'—H21'	0.9300
C22—H22	0.9300	C22'—H22'	0.9300
C23—O3	1.355 (9)	C23'—O3'	1.418 (10)
C23—H23A	0.9600	C23'—H23D	0.9600
C23—H23B	0.9600	C23'—H23E	0.9600
C23—H23C	0.9600	C23'—H23F	0.9600
C2—C1—C6	118.8 (10)	C3'—C2'—C1'	120.9 (10)
C2—C1—C7	121.6 (13)	C3'—C2'—H2'	119.6
C6—C1—C7	119.3 (14)	C1'—C2'—H2'	119.6
C1—C2—C3	120.9 (6)	C4'—C3'—C2'	115.8 (14)
C1—C2—H2	119.5	C4'—C3'—H3'	122.1
C3—C2—H2	119.5	C2'—C3'—H3'	122.1
C2—C3—C4	120.0	C5'—C4'—C3'	124.0 (15)
C2—C3—H3	120.0	C5'—C4'—H4'	118.0
C4—C3—H3	120.0	C3'—C4'—H4'	118.0
C3—C4—C5	120.0	C4'—C5'—C6'	120.6 (12)
C3—C4—H4	120.0	C4'—C5'—H5'	119.7
C5—C4—H4	120.0	C6'—C5'—H5'	119.7
C6—C5—C4	120.0	C16'—C6'—C1'	126 (2)
C6—C5—H5	120.0	C16'—C6'—C5'	116.3 (17)
C4—C5—H5	120.0	C1'—C6'—C5'	117.4 (14)
C16—C6—C5	124.0 (5)	O1'—C7'—C8'	123.2 (16)
C16—C6—C1	115.5 (9)	O1'—C7'—C1'	114.9 (17)
C5—C6—C1	120.1 (7)	C8'—C7'—C1'	121.9 (5)
O1—C7—C8	118.8 (5)	C9'—C8'—C13'	120.0
O1—C7—C1	117.8 (11)	C9'—C8'—C7'	126.9
C8—C7—C1	122.4 (9)	C13'—C8'—C7'	113.1
C9—C8—C13	120.0	C8'—C9'—C10'	120.0
C9—C8—C7	117.5	C8'—C9'—H9'	120.0
C13—C8—C7	122.0	C10'—C9'—H9'	120.0
C8—C9—C10	120.0	C11'—C10'—C9'	120.0
C8—C9—H9	120.0	C11'—C10'—C14'	128.4 (4)
C10—C9—H9	120.0	C9'—C10'—C14'	111.6 (4)
C9—C10—C11	120.0	C10'—C11'—C12'	120.0
C9—C10—C14	121.1 (4)	C10'—C11'—C15'	115.2 (5)
C11—C10—C14	118.7 (4)	C12'—C11'—C15'	124.7 (5)
C12—C11—C10	120.0	C13'—C12'—C11'	120.0
C12—C11—C15	120.2 (3)	C13'—C12'—H12'	120.0
C10—C11—C15	119.7 (3)	C11'—C12'—H12'	120.0
C11—C12—C13	120.0	C12'—C13'—C8'	120.0
C11—C12—H12	120.0	C12'—C13'—H13'	120.0
C13—C12—H12	120.0	C8'—C13'—H13'	120.0
C12—C13—C8	120.0	C10'—C14'—H14D	109.5
C12—C13—H13	120.0	C10'—C14'—H14E	109.5
C8—C13—H13	120.0	H14D—C14'—H14E	109.5
C10—C14—H14A	109.5	C10'—C14'—H14F	109.5
C10—C14—H14B	109.5	H14D—C14'—H14F	109.5
H14A—C14—H14B	109.5	H14E—C14'—H14F	109.5
C10—C14—H14C	109.5	C11'—C15'—H15D	109.5
H14A—C14—H14C	109.5	C11'—C15'—H15E	109.5
H14B—C14—H14C	109.5	H15D—C15'—H15E	109.5
C11—C15—H15A	109.5	C11'—C15'—H15F	109.5
C11—C15—H15B	109.5	H15D—C15'—H15F	109.5
H15A—C15—H15B	109.5	H15E—C15'—H15F	109.5
C11—C15—H15C	109.5	O2'—C16'—C6'	119.0 (16)
H15A—C15—H15C	109.5	O2'—C16'—C17'	127.4 (10)
H15B—C15—H15C	109.5	C6'—C16'—C17'	110.5 (14)
O2—C16—C6	127.3 (14)	C18'—C17'—C22'	120.0
O2—C16—C17	117.3 (12)	C18'—C17'—C16'	126.6
C6—C16—C17	114.9 (4)	C22'—C17'—C16'	112.9
C18—C17—C22	120.0	C17'—C18'—C19'	120.0
C18—C17—C16	114.4	C17'—C18'—H18'	120.0
C22—C17—C16	125.4	C19'—C18'—H18'	120.0
C17—C18—C19	120.0	C20'—C19'—C18'	120.0
C17—C18—H18	120.0	C20'—C19'—H19'	120.0
C19—C18—H18	120.0	C18'—C19'—H19'	120.0
C20—C19—C18	120.0	C19'—C20'—C21'	120.0
C20—C19—H19	120.0	C19'—C20'—O3'	105.9 (3)
C18—C19—H19	120.0	C21'—C20'—O3'	134.1 (3)
C19—C20—C21	120.0	C22'—C21'—C20'	120.0
C19—C20—O3	136.8 (6)	C22'—C21'—H21'	120.0
C21—C20—O3	103.2 (6)	C20'—C21'—H21'	120.0
C22—C21—C20	120.0	C21'—C22'—C17'	120.0
C22—C21—H21	120.0	C21'—C22'—H22'	120.0
C20—C21—H21	120.0	C17'—C22'—H22'	120.0
C21—C22—C17	120.0	O3'—C23'—H23D	109.5
C21—C22—H22	120.0	O3'—C23'—H23E	109.5
C17—C22—H22	120.0	H23D—C23'—H23E	109.5
C23—O3—C20	115.6 (9)	O3'—C23'—H23F	109.5
C6'—C1'—C2'	120.6 (12)	H23D—C23'—H23F	109.5
C6'—C1'—C7'	123.7 (13)	H23E—C23'—H23F	109.5
C2'—C1'—C7'	115.5 (10)	C20'—O3'—C23'	106.9 (8)
C6—C1—C2—C3	−5 (3)	C6'—C1'—C2'—C3'	1 (2)
C7—C1—C2—C3	−178.1 (13)	C7'—C1'—C2'—C3'	−173.8 (12)
C1—C2—C3—C4	2.6 (14)	C1'—C2'—C3'—C4'	−1.4 (17)
C2—C3—C4—C5	0.0	C2'—C3'—C4'—C5'	5.3 (15)
C3—C4—C5—C6	0.0	C3'—C4'—C5'—C6'	−9 (3)
C4—C5—C6—C16	−175.7 (6)	C2'—C1'—C6'—C16'	172 (2)
C4—C5—C6—C1	−2.5 (14)	C7'—C1'—C6'—C16'	−13 (4)
C2—C1—C6—C16	178.8 (16)	C2'—C1'—C6'—C5'	−5 (3)
C7—C1—C6—C16	−8 (3)	C7'—C1'—C6'—C5'	169.8 (17)
C2—C1—C6—C5	5 (3)	C4'—C5'—C6'—C16'	−168.9 (19)
C7—C1—C6—C5	178.2 (12)	C4'—C5'—C6'—C1'	9 (4)
C2—C1—C7—O1	119 (2)	C6'—C1'—C7'—O1'	−55 (3)
C6—C1—C7—O1	−54 (3)	C2'—C1'—C7'—O1'	120.1 (19)
C2—C1—C7—C8	−49 (3)	C6'—C1'—C7'—C8'	126.6 (18)
C6—C1—C7—C8	138.5 (15)	C2'—C1'—C7'—C8'	−58.3 (9)
O1—C7—C8—C9	156.0 (9)	O1'—C7'—C8'—C9'	159.0 (19)
C1—C7—C8—C9	−36.2 (12)	C1'—C7'—C8'—C9'	−22.7 (7)
O1—C7—C8—C13	−16.1 (9)	O1'—C7'—C8'—C13'	−20.8 (19)
C1—C7—C8—C13	151.7 (12)	C1'—C7'—C8'—C13'	157.4 (7)
C13—C8—C9—C10	0.0	C13'—C8'—C9'—C10'	0.0
C7—C8—C9—C10	−172.3	C7'—C8'—C9'—C10'	−179.8
C8—C9—C10—C11	0.0	C8'—C9'—C10'—C11'	0.0
C8—C9—C10—C14	174.4 (5)	C8'—C9'—C10'—C14'	179.4 (5)
C9—C10—C11—C12	0.0	C9'—C10'—C11'—C12'	0.0
C14—C10—C11—C12	−174.5 (5)	C14'—C10'—C11'—C12'	−179.3 (6)
C9—C10—C11—C15	178.8 (5)	C9'—C10'—C11'—C15'	−178.0 (8)
C14—C10—C11—C15	4.3 (6)	C14'—C10'—C11'—C15'	2.7 (8)
C10—C11—C12—C13	0.0	C10'—C11'—C12'—C13'	0.0
C15—C11—C12—C13	−178.8 (5)	C15'—C11'—C12'—C13'	177.8 (8)
C11—C12—C13—C8	0.0	C11'—C12'—C13'—C8'	0.0
C9—C8—C13—C12	0.0	C9'—C8'—C13'—C12'	0.0
C7—C8—C13—C12	171.9	C7'—C8'—C13'—C12'	179.8
C5—C6—C16—O2	124.1 (16)	C1'—C6'—C16'—O2'	−42 (4)
C1—C6—C16—O2	−49 (2)	C5'—C6'—C16'—O2'	135 (2)
C5—C6—C16—C17	−48.6 (6)	C1'—C6'—C16'—C17'	119 (3)
C1—C6—C16—C17	138.0 (13)	C5'—C6'—C16'—C17'	−63 (3)
O2—C16—C17—C18	151.6 (14)	O2'—C16'—C17'—C18'	145.8 (17)
C6—C16—C17—C18	−35.0 (6)	C6'—C16'—C17'—C18'	−14.0 (14)
O2—C16—C17—C22	−23.9 (14)	O2'—C16'—C17'—C22'	−42.1 (17)
C6—C16—C17—C22	149.5 (6)	C6'—C16'—C17'—C22'	158.1 (14)
C22—C17—C18—C19	0.0	C22'—C17'—C18'—C19'	0.0
C16—C17—C18—C19	−175.8	C16'—C17'—C18'—C19'	171.6
C17—C18—C19—C20	0.0	C17'—C18'—C19'—C20'	0.0
C18—C19—C20—C21	0.0	C18'—C19'—C20'—C21'	0.0
C18—C19—C20—O3	179.0 (8)	C18'—C19'—C20'—O3'	178.0 (4)
C19—C20—C21—C22	0.0	C19'—C20'—C21'—C22'	0.0
O3—C20—C21—C22	−179.3 (6)	O3'—C20'—C21'—C22'	−177.4 (5)
C20—C21—C22—C17	0.0	C20'—C21'—C22'—C17'	0.0
C18—C17—C22—C21	0.0	C18'—C17'—C22'—C21'	0.0
C16—C17—C22—C21	175.3	C16'—C17'—C22'—C21'	−172.7
C19—C20—O3—C23	1.4 (15)	C19'—C20'—O3'—C23'	178.1 (8)
C21—C20—O3—C23	−179.5 (10)	C21'—C20'—O3'—C23'	−4.2 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23B···O2i	0.96	2.32	3.23 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23B⋯O2i	0.96	2.32	3.23 (3)	159

Symmetry code: (i) .