(2,7-Di-meth-oxy-naphthalen-1-yl)(naph-thalen-1-yl)methanone.

The asymmetric unit of the title compound, C23H18O3, contains two independent mol-ecules (A and B). Each mol-ecule has essentially the same conformation (r.m.s. deviation of fitted mol-ecules = 0.173 Å) with the aromatic rings twisted in a near perpendicular manner. The dihedral angles between the two naphthalene ring systems are 79.07 (4) and 88.19 (4)° in the two independent mol-ecules. In the crystal, the A mol-ecules are connected by C-H⋯O inter-actions, forming chains along the b-axis direction. Further C-H⋯O inter-actions between the H atoms of the meth-oxy group and the O atoms of the carbonyl units link the A and B mol-ecules, forming a three-dimensional network.

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Nakaema et al. (2008 ▶); Kato et al. (2010 ▶); Tsumuki et al. (2012 ▶, 2013 ▶); Sasagawa et al. (2013 ▶).

Experimental

Crystal data

C23H18O3

M = 342.37

Monoclinic,

a = 16.1451 (3) Å

b = 7.51303 (14) Å

c = 29.0107 (5) Å

β = 98.547 (1)°

V = 3479.88 (11) Å3

Z = 8

Cu Kα radiation

μ = 0.69 mm−1

T = 193 K

0.50 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.725, T max = 0.934

62016 measured reflections

6349 independent reflections

5490 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.07

6349 reflections

470 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008854/vm2191sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008854/vm2191Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008854/vm2191Isup3.cml

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

C23H18O3	F(000) = 1440
Mr = 342.37	Dx = 1.307 Mg m−3
Monoclinic, P21/n	Melting point = 391.4–392.7 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54187 Å
a = 16.1451 (3) Å	Cell parameters from 51750 reflections
b = 7.51303 (14) Å	θ = 3.0–68.2°
c = 29.0107 (5) Å	µ = 0.69 mm−1
β = 98.547 (1)°	T = 193 K
V = 3479.88 (11) Å3	Platelet, yellow
Z = 8	0.50 × 0.20 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	6349 independent reflections
Radiation source: fine-focus sealed tube	5490 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.0°
ω scans	h = −19→19
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −8→8
Tmin = 0.725, Tmax = 0.934	l = −34→34
62016 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6272P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
6349 reflections	Δρmax = 0.21 e Å−3
470 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00173 (12)

Experimental. Spectroscopic data for the title compound: 1H NMR δ (500 MHz, CDCl3): 3.67 (3H, s), 3.68 (3H, s), 7.02–7.05 (2H, m), 7.14 (1H, dd, J = 1.2, 8.6 Hz), 7.34 (1H, t, J = 8.6 Hz), 7.58–7.61 (2H, m), 7.69–7.74 (2H, m), 7.88 (1H, d, J = 8.6 Hz), 7.93 (1H, d, J = 8.6 Hz), 8.00 (1H, d, J = 8.6 Hz), 9.14 (1H, d, J = 8.6 Hz) p.p.m.; 13C NMR δ (125 MHz, CDCl3): 55.15, 56.41, 102.10, 110.57, 117.19, 123.94, 124.39,124.50, 126.17, 126.42, 128.28, 128.42, 129.61, 130.71, 131.20, 131.27, 132.14,133.39, 133.96, 136.20, 155.53, 159.08, 200.04 p.p.m.; IR (KBr): 1652, 1623,1510, 1250, 1227 cm-1; HRMS (m/z): [M+H]+ calcd. for C23H19O3, 343.1334, found, 343.1310.

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 > 2σ(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
O1	1.01615 (7)	0.12392 (16)	0.33256 (3)	0.0616 (3)
O2	0.70559 (6)	0.15461 (14)	0.12536 (3)	0.0508 (2)
O3	0.89345 (7)	−0.05216 (13)	0.15993 (4)	0.0622 (3)
O4	0.26783 (6)	−0.25199 (14)	0.10328 (3)	0.0554 (3)
O5	0.40252 (6)	0.56893 (14)	0.00664 (3)	0.0569 (3)
O6	0.43705 (6)	0.04372 (18)	0.12626 (3)	0.0639 (3)
C1	0.79575 (10)	0.21648 (19)	0.31798 (5)	0.0494 (3)
H1	0.7553	0.2445	0.3375	0.059*
C2	0.68602 (9)	0.21983 (18)	0.24859 (5)	0.0462 (3)
H2	0.6449	0.2450	0.2679	0.055*
C3	0.87670 (10)	0.1930 (2)	0.33734 (5)	0.0529 (4)
H3	0.8925	0.2048	0.3701	0.063*
C4	0.76993 (8)	0.20020 (17)	0.26918 (4)	0.0421 (3)
C5	0.66176 (8)	0.20393 (18)	0.20164 (5)	0.0467 (3)
H5	0.6045	0.2154	0.1886	0.056*
C6	0.93771 (9)	0.15083 (18)	0.30871 (5)	0.0471 (3)
C7	0.83205 (8)	0.16239 (16)	0.24039 (4)	0.0382 (3)
C8	0.72308 (8)	0.17014 (17)	0.17282 (4)	0.0411 (3)
C9	0.91635 (8)	0.13863 (17)	0.26125 (4)	0.0417 (3)
H9	0.9582	0.1142	0.2423	0.050*
C10	0.80601 (8)	0.14999 (16)	0.19160 (4)	0.0379 (3)
C11	1.08006 (10)	0.0764 (3)	0.30625 (6)	0.0700 (5)
H11A	1.0859	0.1701	0.2834	0.084*
H11B	1.0653	−0.0360	0.2899	0.084*
H11C	1.1332	0.0624	0.3272	0.084*
C12	0.62104 (9)	0.1748 (2)	0.10372 (5)	0.0599 (4)
H12A	0.5994	0.2897	0.1126	0.072*
H12B	0.5870	0.0786	0.1139	0.072*
H12C	0.6185	0.1699	0.0698	0.072*
C13	0.86907 (8)	0.10129 (17)	0.16010 (4)	0.0390 (3)
C14	0.90082 (7)	0.24390 (16)	0.13158 (4)	0.0347 (3)
C15	0.99264 (7)	0.04222 (18)	0.09065 (4)	0.0409 (3)
H15	0.9762	−0.0593	0.1066	0.049*
C16	0.87278 (8)	0.41462 (17)	0.13703 (4)	0.0409 (3)
H16	0.8343	0.4354	0.1583	0.049*
C17	0.95957 (7)	0.21113 (17)	0.09948 (4)	0.0345 (3)
C18	1.04813 (8)	0.0228 (2)	0.05938 (5)	0.0472 (3)
H18	1.0688	−0.0924	0.0537	0.057*
C19	0.89927 (9)	0.55883 (18)	0.11217 (5)	0.0468 (3)
H19	0.8787	0.6751	0.1166	0.056*
C20	0.98600 (7)	0.35935 (17)	0.07484 (4)	0.0383 (3)
C21	1.07479 (8)	0.1691 (2)	0.03572 (4)	0.0468 (3)
H21	1.1138	0.1539	0.0145	0.056*
C22	0.95445 (8)	0.53152 (18)	0.08181 (5)	0.0454 (3)
H22	0.9721	0.6295	0.0650	0.055*
C23	1.04435 (8)	0.33343 (19)	0.04336 (4)	0.0441 (3)
H23	1.0625	0.4330	0.0273	0.053*
C24	0.28062 (9)	0.2044 (2)	−0.04715 (5)	0.0553 (4)
H24	0.2535	0.1747	−0.0775	0.066*
C25	0.23599 (8)	−0.0818 (2)	−0.01668 (5)	0.0514 (4)
H25	0.2100	−0.1140	−0.0471	0.062*
C26	0.32023 (10)	0.3634 (2)	−0.04014 (5)	0.0563 (4)
H26	0.3190	0.4453	−0.0652	0.068*
C27	0.27864 (8)	0.0814 (2)	−0.01026 (4)	0.0462 (3)
C28	0.23074 (8)	−0.1957 (2)	0.01966 (5)	0.0505 (3)
H28	0.2013	−0.3052	0.0146	0.061*
C29	0.36339 (8)	0.4072 (2)	0.00453 (5)	0.0485 (3)
C30	0.32048 (7)	0.12731 (19)	0.03493 (4)	0.0421 (3)
C31	0.26984 (8)	−0.14760 (19)	0.06465 (5)	0.0453 (3)
C32	0.36395 (8)	0.29237 (19)	0.04120 (4)	0.0443 (3)
H32	0.3934	0.3230	0.0710	0.053*
C33	0.31488 (8)	0.00766 (19)	0.07226 (4)	0.0420 (3)
C34	0.44996 (10)	0.6200 (2)	0.05015 (5)	0.0582 (4)
H34A	0.4968	0.5373	0.0582	0.070*
H34B	0.4139	0.6169	0.0745	0.070*
H34C	0.4717	0.7409	0.0476	0.070*
C35	0.21515 (10)	−0.4043 (2)	0.09906 (6)	0.0609 (4)
H35A	0.1574	−0.3683	0.0876	0.073*
H35B	0.2173	−0.4613	0.1296	0.073*
H35C	0.2343	−0.4886	0.0771	0.073*
C36	0.36123 (8)	0.04884 (19)	0.12026 (4)	0.0425 (3)
C37	0.31181 (8)	0.10627 (17)	0.15718 (4)	0.0387 (3)
C38	0.43097 (8)	0.0746 (2)	0.22378 (5)	0.0491 (3)
H38	0.4649	0.0167	0.2042	0.059*
C39	0.22936 (8)	0.15209 (18)	0.14364 (4)	0.0438 (3)
H39	0.2047	0.1315	0.1123	0.053*
C40	0.34895 (8)	0.12952 (18)	0.20514 (4)	0.0404 (3)
C41	0.46189 (10)	0.1041 (3)	0.26970 (5)	0.0623 (4)
H41	0.5167	0.0645	0.2818	0.075*
C42	0.18033 (9)	0.2282 (2)	0.17458 (5)	0.0503 (3)
H42	0.1233	0.2568	0.1643	0.060*
C43	0.29889 (9)	0.21202 (19)	0.23588 (5)	0.0460 (3)
C44	0.41358 (11)	0.1922 (3)	0.29922 (5)	0.0682 (5)
H44	0.4367	0.2159	0.3307	0.082*
C45	0.21523 (9)	0.26059 (19)	0.21939 (5)	0.0503 (3)
H45	0.1828	0.3169	0.2400	0.060*
C46	0.33410 (11)	0.2433 (2)	0.28285 (5)	0.0591 (4)
H46	0.3016	0.3009	0.3032	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0597 (6)	0.0755 (8)	0.0473 (6)	0.0055 (5)	0.0005 (5)	−0.0061 (5)
O2	0.0410 (5)	0.0697 (7)	0.0426 (5)	−0.0012 (4)	0.0086 (4)	−0.0032 (4)
O3	0.0889 (8)	0.0381 (6)	0.0710 (7)	0.0088 (5)	0.0490 (6)	0.0040 (5)
O4	0.0575 (6)	0.0554 (6)	0.0525 (6)	−0.0099 (5)	0.0060 (4)	0.0040 (5)
O5	0.0605 (6)	0.0588 (7)	0.0532 (6)	0.0020 (5)	0.0145 (5)	0.0091 (5)
O6	0.0373 (5)	0.1113 (10)	0.0429 (5)	−0.0012 (5)	0.0053 (4)	0.0015 (6)
C1	0.0653 (9)	0.0448 (8)	0.0432 (7)	0.0004 (7)	0.0247 (6)	−0.0036 (6)
C2	0.0507 (7)	0.0416 (7)	0.0519 (8)	0.0010 (6)	0.0257 (6)	−0.0020 (6)
C3	0.0709 (9)	0.0524 (9)	0.0371 (7)	0.0003 (7)	0.0136 (6)	−0.0045 (6)
C4	0.0517 (7)	0.0344 (7)	0.0443 (7)	−0.0010 (5)	0.0208 (6)	−0.0022 (5)
C5	0.0410 (7)	0.0462 (8)	0.0559 (8)	0.0014 (6)	0.0164 (6)	−0.0001 (6)
C6	0.0553 (8)	0.0429 (8)	0.0432 (7)	−0.0019 (6)	0.0080 (6)	−0.0028 (6)
C7	0.0470 (7)	0.0308 (6)	0.0398 (6)	−0.0027 (5)	0.0158 (5)	−0.0017 (5)
C8	0.0449 (7)	0.0396 (7)	0.0408 (7)	−0.0013 (5)	0.0128 (5)	−0.0015 (5)
C9	0.0471 (7)	0.0385 (7)	0.0419 (7)	−0.0016 (5)	0.0142 (5)	−0.0037 (5)
C10	0.0424 (6)	0.0344 (7)	0.0394 (6)	−0.0020 (5)	0.0144 (5)	−0.0021 (5)
C11	0.0542 (9)	0.0850 (13)	0.0675 (10)	0.0114 (8)	−0.0017 (8)	−0.0125 (9)
C12	0.0455 (8)	0.0787 (11)	0.0542 (8)	0.0037 (7)	0.0036 (6)	0.0021 (8)
C13	0.0435 (6)	0.0381 (7)	0.0371 (6)	−0.0011 (5)	0.0121 (5)	−0.0043 (5)
C14	0.0335 (6)	0.0387 (7)	0.0318 (6)	−0.0007 (5)	0.0044 (4)	−0.0031 (5)
C15	0.0377 (6)	0.0428 (7)	0.0438 (7)	0.0009 (5)	0.0110 (5)	0.0004 (5)
C16	0.0428 (6)	0.0397 (7)	0.0415 (6)	0.0007 (5)	0.0112 (5)	−0.0053 (5)
C17	0.0301 (5)	0.0425 (7)	0.0302 (5)	−0.0020 (5)	0.0024 (4)	−0.0030 (5)
C18	0.0418 (7)	0.0504 (8)	0.0513 (7)	0.0047 (6)	0.0134 (6)	−0.0060 (6)
C19	0.0536 (8)	0.0363 (7)	0.0517 (7)	0.0027 (6)	0.0116 (6)	−0.0003 (6)
C20	0.0364 (6)	0.0449 (7)	0.0331 (6)	−0.0035 (5)	0.0031 (5)	−0.0006 (5)
C21	0.0376 (6)	0.0643 (9)	0.0409 (7)	−0.0009 (6)	0.0135 (5)	−0.0043 (6)
C22	0.0525 (7)	0.0410 (7)	0.0431 (7)	−0.0054 (6)	0.0078 (6)	0.0049 (6)
C23	0.0406 (6)	0.0550 (8)	0.0372 (6)	−0.0075 (6)	0.0079 (5)	0.0021 (6)
C24	0.0510 (8)	0.0819 (11)	0.0329 (7)	0.0076 (8)	0.0059 (6)	0.0000 (7)
C25	0.0404 (7)	0.0739 (10)	0.0397 (7)	0.0040 (7)	0.0051 (5)	−0.0139 (7)
C26	0.0573 (8)	0.0737 (11)	0.0394 (7)	0.0094 (8)	0.0117 (6)	0.0113 (7)
C27	0.0381 (6)	0.0671 (9)	0.0341 (6)	0.0077 (6)	0.0079 (5)	−0.0053 (6)
C28	0.0408 (7)	0.0597 (9)	0.0512 (8)	−0.0009 (6)	0.0074 (6)	−0.0134 (7)
C29	0.0444 (7)	0.0586 (9)	0.0449 (7)	0.0074 (6)	0.0142 (6)	0.0036 (6)
C30	0.0355 (6)	0.0566 (8)	0.0350 (6)	0.0065 (6)	0.0086 (5)	−0.0026 (6)
C31	0.0384 (6)	0.0543 (8)	0.0438 (7)	0.0026 (6)	0.0081 (5)	−0.0022 (6)
C32	0.0404 (6)	0.0573 (8)	0.0361 (6)	0.0038 (6)	0.0087 (5)	−0.0001 (6)
C33	0.0368 (6)	0.0528 (8)	0.0366 (6)	0.0027 (6)	0.0066 (5)	−0.0028 (6)
C34	0.0562 (8)	0.0581 (9)	0.0617 (9)	−0.0018 (7)	0.0130 (7)	0.0001 (7)
C35	0.0583 (9)	0.0548 (9)	0.0710 (10)	−0.0091 (7)	0.0144 (7)	−0.0016 (8)
C36	0.0386 (6)	0.0508 (8)	0.0376 (6)	−0.0023 (6)	0.0042 (5)	0.0052 (6)
C37	0.0401 (6)	0.0398 (7)	0.0358 (6)	−0.0048 (5)	0.0047 (5)	0.0021 (5)
C38	0.0453 (7)	0.0608 (9)	0.0399 (7)	−0.0078 (6)	0.0015 (5)	0.0063 (6)
C39	0.0428 (7)	0.0485 (8)	0.0393 (7)	−0.0003 (6)	0.0029 (5)	0.0009 (6)
C40	0.0436 (7)	0.0409 (7)	0.0363 (6)	−0.0085 (5)	0.0045 (5)	0.0025 (5)
C41	0.0531 (8)	0.0844 (12)	0.0452 (8)	−0.0132 (8)	−0.0063 (6)	0.0080 (8)
C42	0.0440 (7)	0.0530 (9)	0.0541 (8)	0.0053 (6)	0.0083 (6)	0.0008 (6)
C43	0.0554 (8)	0.0425 (8)	0.0408 (7)	−0.0099 (6)	0.0099 (6)	−0.0012 (6)
C44	0.0762 (11)	0.0868 (13)	0.0385 (8)	−0.0232 (9)	−0.0022 (7)	−0.0059 (8)
C45	0.0563 (8)	0.0458 (8)	0.0518 (8)	−0.0004 (6)	0.0180 (6)	−0.0033 (6)
C46	0.0749 (10)	0.0619 (10)	0.0409 (7)	−0.0145 (8)	0.0102 (7)	−0.0089 (7)

O1—C6	1.3648 (17)	C20—C23	1.4196 (17)
O1—C11	1.4173 (19)	C21—C23	1.359 (2)
O2—C8	1.3690 (15)	C21—H21	0.9500
O2—C12	1.4232 (17)	C22—H22	0.9500
O3—C13	1.2185 (16)	C23—H23	0.9500
O4—C31	1.3723 (16)	C24—C26	1.356 (2)
O4—C35	1.4203 (18)	C24—C27	1.418 (2)
O5—C29	1.3669 (18)	C24—H24	0.9500
O5—C34	1.4283 (18)	C25—C28	1.371 (2)
O6—C36	1.2111 (15)	C25—C27	1.404 (2)
C1—C3	1.355 (2)	C25—H25	0.9500
C1—C4	1.4206 (19)	C26—C29	1.416 (2)
C1—H1	0.9500	C26—H26	0.9500
C2—C5	1.365 (2)	C27—C30	1.4250 (17)
C2—C4	1.405 (2)	C28—C31	1.4099 (19)
C2—H2	0.9500	C28—H28	0.9500
C3—C6	1.415 (2)	C29—C32	1.3686 (19)
C3—H3	0.9500	C30—C33	1.4208 (18)
C4—C7	1.4257 (17)	C30—C32	1.423 (2)
C5—C8	1.4104 (17)	C31—C33	1.3749 (19)
C5—H5	0.9500	C32—H32	0.9500
C6—C9	1.3718 (18)	C33—C36	1.5116 (17)
C7—C9	1.4163 (18)	C34—H34A	0.9800
C7—C10	1.4187 (17)	C34—H34B	0.9800
C8—C10	1.3767 (18)	C34—H34C	0.9800
C9—H9	0.9500	C35—H35A	0.9800
C10—C13	1.5106 (16)	C35—H35B	0.9800
C11—H11A	0.9800	C35—H35C	0.9800
C11—H11B	0.9800	C36—C37	1.4913 (18)
C11—H11C	0.9800	C37—C39	1.3745 (18)
C12—H12A	0.9800	C37—C40	1.4417 (17)
C12—H12B	0.9800	C38—C41	1.3694 (19)
C12—H12C	0.9800	C38—C40	1.4154 (18)
C13—C14	1.4904 (17)	C38—H38	0.9500
C14—C16	1.3772 (18)	C39—C42	1.4036 (19)
C14—C17	1.4457 (16)	C39—H39	0.9500
C15—C18	1.3742 (17)	C40—C43	1.4307 (19)
C15—C17	1.4148 (18)	C41—C44	1.406 (3)
C15—H15	0.9500	C41—H41	0.9500
C16—C19	1.4031 (19)	C42—C45	1.360 (2)
C16—H16	0.9500	C42—H42	0.9500
C17—C20	1.4226 (17)	C43—C45	1.412 (2)
C18—C21	1.397 (2)	C43—C46	1.4160 (19)
C18—H18	0.9500	C44—C46	1.356 (2)
C19—C22	1.3583 (19)	C44—H44	0.9500
C19—H19	0.9500	C45—H45	0.9500
C20—C22	1.4156 (19)	C46—H46	0.9500
C6—O1—C11	117.34 (11)	C21—C23—H23	119.3
C8—O2—C12	118.39 (10)	C20—C23—H23	119.3
C31—O4—C35	118.47 (12)	C26—C24—C27	121.61 (13)
C29—O5—C34	117.53 (11)	C26—C24—H24	119.2
C3—C1—C4	121.59 (12)	C27—C24—H24	119.2
C3—C1—H1	119.2	C28—C25—C27	121.89 (13)
C4—C1—H1	119.2	C28—C25—H25	119.1
C5—C2—C4	122.04 (12)	C27—C25—H25	119.1
C5—C2—H2	119.0	C24—C26—C29	119.94 (14)
C4—C2—H2	119.0	C24—C26—H26	120.0
C1—C3—C6	119.90 (12)	C29—C26—H26	120.0
C1—C3—H3	120.1	C25—C27—C24	122.30 (13)
C6—C3—H3	120.1	C25—C27—C30	119.30 (13)
C2—C4—C1	122.43 (12)	C24—C27—C30	118.39 (14)
C2—C4—C7	119.33 (12)	C25—C28—C31	118.77 (14)
C1—C4—C7	118.24 (12)	C25—C28—H28	120.6
C2—C5—C8	118.98 (12)	C31—C28—H28	120.6
C2—C5—H5	120.5	O5—C29—C32	125.16 (13)
C8—C5—H5	120.5	O5—C29—C26	114.14 (13)
O1—C6—C9	125.09 (13)	C32—C29—C26	120.70 (14)
O1—C6—C3	114.20 (12)	C33—C30—C32	122.67 (11)
C9—C6—C3	120.71 (13)	C33—C30—C27	118.22 (13)
C9—C7—C10	122.79 (11)	C32—C30—C27	119.08 (12)
C9—C7—C4	119.34 (11)	O4—C31—C33	115.45 (12)
C10—C7—C4	117.88 (12)	O4—C31—C28	123.21 (13)
O2—C8—C10	115.57 (11)	C33—C31—C28	121.32 (13)
O2—C8—C5	123.61 (12)	C29—C32—C30	120.23 (12)
C10—C8—C5	120.82 (12)	C29—C32—H32	119.9
C6—C9—C7	120.18 (12)	C30—C32—H32	119.9
C6—C9—H9	119.9	C31—C33—C30	120.42 (12)
C7—C9—H9	119.9	C31—C33—C36	119.95 (12)
C8—C10—C7	120.93 (11)	C30—C33—C36	119.60 (12)
C8—C10—C13	119.38 (11)	O5—C34—H34A	109.5
C7—C10—C13	119.54 (11)	O5—C34—H34B	109.5
O1—C11—H11A	109.5	H34A—C34—H34B	109.5
O1—C11—H11B	109.5	O5—C34—H34C	109.5
H11A—C11—H11B	109.5	H34A—C34—H34C	109.5
O1—C11—H11C	109.5	H34B—C34—H34C	109.5
H11A—C11—H11C	109.5	O4—C35—H35A	109.5
H11B—C11—H11C	109.5	O4—C35—H35B	109.5
O2—C12—H12A	109.5	H35A—C35—H35B	109.5
O2—C12—H12B	109.5	O4—C35—H35C	109.5
H12A—C12—H12B	109.5	H35A—C35—H35C	109.5
O2—C12—H12C	109.5	H35B—C35—H35C	109.5
H12A—C12—H12C	109.5	O6—C36—C37	122.90 (12)
H12B—C12—H12C	109.5	O6—C36—C33	118.52 (11)
O3—C13—C14	122.68 (11)	C37—C36—C33	118.44 (10)
O3—C13—C10	118.61 (11)	C39—C37—C40	119.45 (12)
C14—C13—C10	118.69 (11)	C39—C37—C36	117.78 (11)
C16—C14—C17	119.40 (11)	C40—C37—C36	122.55 (11)
C16—C14—C13	117.37 (10)	C41—C38—C40	120.63 (14)
C17—C14—C13	123.22 (11)	C41—C38—H38	119.7
C18—C15—C17	121.02 (12)	C40—C38—H38	119.7
C18—C15—H15	119.5	C37—C39—C42	122.25 (12)
C17—C15—H15	119.5	C37—C39—H39	118.9
C14—C16—C19	121.98 (11)	C42—C39—H39	118.9
C14—C16—H16	119.0	C38—C40—C43	118.12 (12)
C19—C16—H16	119.0	C38—C40—C37	124.39 (12)
C15—C17—C20	117.50 (10)	C43—C40—C37	117.49 (12)
C15—C17—C14	124.80 (11)	C38—C41—C44	120.90 (15)
C20—C17—C14	117.70 (11)	C38—C41—H41	119.6
C15—C18—C21	121.29 (13)	C44—C41—H41	119.6
C15—C18—H18	119.4	C45—C42—C39	119.43 (13)
C21—C18—H18	119.4	C45—C42—H42	120.3
C22—C19—C16	119.74 (12)	C39—C42—H42	120.3
C22—C19—H19	120.1	C45—C43—C46	120.67 (13)
C16—C19—H19	120.1	C45—C43—C40	120.09 (12)
C22—C20—C23	120.30 (12)	C46—C43—C40	119.24 (13)
C22—C20—C17	120.15 (11)	C46—C44—C41	120.11 (14)
C23—C20—C17	119.55 (12)	C46—C44—H44	119.9
C23—C21—C18	119.29 (11)	C41—C44—H44	119.9
C23—C21—H21	120.4	C42—C45—C43	121.14 (13)
C18—C21—H21	120.4	C42—C45—H45	119.4
C19—C22—C20	121.01 (12)	C43—C45—H45	119.4
C19—C22—H22	119.5	C44—C46—C43	120.91 (15)
C20—C22—H22	119.5	C44—C46—H46	119.5
C21—C23—C20	121.34 (12)	C43—C46—H46	119.5
C4—C1—C3—C6	−0.1 (2)	C27—C24—C26—C29	2.2 (2)
C5—C2—C4—C1	−179.99 (13)	C28—C25—C27—C24	−176.55 (13)
C5—C2—C4—C7	0.0 (2)	C28—C25—C27—C30	2.44 (19)
C3—C1—C4—C2	178.43 (14)	C26—C24—C27—C25	178.25 (13)
C3—C1—C4—C7	−1.5 (2)	C26—C24—C27—C30	−0.7 (2)
C4—C2—C5—C8	−1.2 (2)	C27—C25—C28—C31	−0.4 (2)
C11—O1—C6—C9	−1.3 (2)	C34—O5—C29—C32	2.10 (19)
C11—O1—C6—C3	178.34 (14)	C34—O5—C29—C26	−177.82 (12)
C1—C3—C6—O1	−177.64 (13)	C24—C26—C29—O5	178.30 (13)
C1—C3—C6—C9	2.0 (2)	C24—C26—C29—C32	−1.6 (2)
C2—C4—C7—C9	−178.59 (12)	C25—C27—C30—C33	−2.09 (18)
C1—C4—C7—C9	1.37 (18)	C24—C27—C30—C33	176.95 (12)
C2—C4—C7—C10	1.32 (18)	C25—C27—C30—C32	179.70 (11)
C1—C4—C7—C10	−178.72 (12)	C24—C27—C30—C32	−1.26 (18)
C12—O2—C8—C10	−179.74 (13)	C35—O4—C31—C33	173.24 (12)
C12—O2—C8—C5	0.4 (2)	C35—O4—C31—C28	−8.38 (19)
C2—C5—C8—O2	−178.97 (12)	C25—C28—C31—O4	179.66 (12)
C2—C5—C8—C10	1.2 (2)	C25—C28—C31—C33	−2.0 (2)
O1—C6—C9—C7	177.46 (13)	O5—C29—C32—C30	179.68 (12)
C3—C6—C9—C7	−2.1 (2)	C26—C29—C32—C30	−0.41 (19)
C10—C7—C9—C6	−179.49 (12)	C33—C30—C32—C29	−176.30 (12)
C4—C7—C9—C6	0.42 (19)	C27—C30—C32—C29	1.83 (18)
O2—C8—C10—C7	−179.73 (11)	O4—C31—C33—C30	−179.23 (11)
C5—C8—C10—C7	0.1 (2)	C28—C31—C33—C30	2.35 (19)
O2—C8—C10—C13	−4.04 (18)	O4—C31—C33—C36	2.86 (17)
C5—C8—C10—C13	175.77 (12)	C28—C31—C33—C36	−175.56 (12)
C9—C7—C10—C8	178.56 (12)	C32—C30—C33—C31	177.89 (12)
C4—C7—C10—C8	−1.35 (18)	C27—C30—C33—C31	−0.25 (18)
C9—C7—C10—C13	2.88 (18)	C32—C30—C33—C36	−4.19 (18)
C4—C7—C10—C13	−177.03 (11)	C27—C30—C33—C36	177.66 (11)
C8—C10—C13—O3	−102.32 (16)	C31—C33—C36—O6	109.71 (15)
C7—C10—C13—O3	73.42 (17)	C30—C33—C36—O6	−68.22 (18)
C8—C10—C13—C14	79.48 (15)	C31—C33—C36—C37	−74.50 (17)
C7—C10—C13—C14	−104.78 (13)	C30—C33—C36—C37	107.57 (14)
O3—C13—C14—C16	−175.74 (13)	O6—C36—C37—C39	163.18 (14)
C10—C13—C14—C16	2.38 (16)	C33—C36—C37—C39	−12.41 (18)
O3—C13—C14—C17	3.47 (19)	O6—C36—C37—C40	−11.4 (2)
C10—C13—C14—C17	−178.41 (11)	C33—C36—C37—C40	172.99 (12)
C17—C14—C16—C19	0.23 (18)	C40—C37—C39—C42	2.7 (2)
C13—C14—C16—C19	179.47 (11)	C36—C37—C39—C42	−172.09 (13)
C18—C15—C17—C20	−0.06 (18)	C41—C38—C40—C43	−1.6 (2)
C18—C15—C17—C14	179.79 (11)	C41—C38—C40—C37	179.08 (13)
C16—C14—C17—C15	−179.70 (11)	C39—C37—C40—C38	174.95 (13)
C13—C14—C17—C15	1.10 (18)	C36—C37—C40—C38	−10.5 (2)
C16—C14—C17—C20	0.15 (16)	C39—C37—C40—C43	−4.35 (19)
C13—C14—C17—C20	−179.05 (10)	C36—C37—C40—C43	170.16 (12)
C17—C15—C18—C21	0.9 (2)	C40—C38—C41—C44	−1.1 (2)
C14—C16—C19—C22	−0.2 (2)	C37—C39—C42—C45	0.9 (2)
C15—C17—C20—C22	179.35 (11)	C38—C40—C43—C45	−176.72 (13)
C14—C17—C20—C22	−0.51 (16)	C37—C40—C43—C45	2.63 (19)
C15—C17—C20—C23	−0.84 (16)	C38—C40—C43—C46	2.97 (19)
C14—C17—C20—C23	179.30 (10)	C37—C40—C43—C46	−177.68 (12)
C15—C18—C21—C23	−0.9 (2)	C38—C41—C44—C46	2.5 (3)
C16—C19—C22—C20	−0.1 (2)	C39—C42—C45—C43	−2.7 (2)
C23—C20—C22—C19	−179.29 (12)	C46—C43—C45—C42	−178.78 (14)
C17—C20—C22—C19	0.52 (19)	C40—C43—C45—C42	0.9 (2)
C18—C21—C23—C20	−0.06 (19)	C41—C44—C46—C43	−1.1 (3)
C22—C20—C23—C21	−179.27 (12)	C45—C43—C46—C44	178.04 (15)
C17—C20—C23—C21	0.92 (18)	C40—C43—C46—C44	−1.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O6	0.98	2.51	3.2862 (18)	136
C19—H19···O3i	0.95	2.40	3.2418 (17)	148
C15—H15···O3	0.95	2.19	2.8397 (16)	125
C38—H38···O6	0.95	2.25	2.8548 (17)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯O6	0.98	2.51	3.2862 (18)	136
C19—H19⋯O3i	0.95	2.40	3.2418 (17)	148
C15—H15⋯O3	0.95	2.19	2.8397 (16)	125
C38—H38⋯O6	0.95	2.25	2.8548 (17)	121

Symmetry code: (i) .