[2,7-Dimeth-oxy-8-(4-meth-oxy-benzo-yl)naphthalen-1-yl](4-meth-oxy-phen-yl)methanone chloro-form monosolvate.

In the title compound, C28H24O6·CHCl3, the two 4-meth-oxy-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, the benzene rings making a dihedral angle of 25.76 (7)°. The naphthalene ring system makes dihedral angles of 72.51 (7) and 73.33 (7)° with the benzene rings. In the crystal, the naphthalene mol-ecules are linked by C-H⋯O inter-actions, forming a helical chain along the b-axis direction. A C-H⋯Cl inter-action is also observed between the aroylated naphthalene and chloro-form mol-ecules. The chloro-form mol-ecule is disordered over two positions with site occupancies of 0.478 (5) and 0.522 (5).

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto et al. (2011 ▶); Okamoto & Yonezawa (2009 ▶). For structures of closely related compounds, see: Hijikata et al. (2010 ▶); Sasagawa et al. (2011 ▶).

Experimental

Crystal data

C28H24O6·CHCl3

M = 575.84

Monoclinic,

a = 8.2781 (2) Å

b = 21.4763 (5) Å

c = 15.5370 (4) Å

β = 98.448 (2)°

V = 2732.25 (12) Å3

Z = 4

Cu Kα radiation

μ = 3.39 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 = 0.282, T max = 0.728

50703 measured reflections

4994 independent reflections

4305 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.107

S = 1.10

4994 reflections

385 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.35 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536812050799/is5230sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050799/is5230Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050799/is5230Isup3.cml

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

C28H24O6·CHCl3	F(000) = 1192
Mr = 575.84	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 37515 reflections
a = 8.2781 (2) Å	θ = 3.5–68.2°
b = 21.4763 (5) Å	µ = 3.39 mm−1
c = 15.5370 (4) Å	T = 193 K
β = 98.448 (2)°	Platelet, colorless
V = 2732.25 (12) Å3	0.50 × 0.20 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4994 independent reflections
Radiation source: fine-focus sealed tube	4305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.5°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→25
Tmin = 0.282, Tmax = 0.728	l = −18→18
50703 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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2582P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.004
4994 reflections	Δρmax = 0.24 e Å−3
385 parameters	Δρmin = −0.35 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: 0.00145 (17)

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)
C29	0.8351 (7)	0.64681 (19)	1.3342 (2)	0.0602 (12)	0.478 (5)
H29	0.9494	0.6434	1.3210	0.072*	0.478 (5)
Cl1	0.7003 (8)	0.5922 (3)	1.2794 (4)	0.0895 (14)	0.478 (5)
Cl2	0.8176 (5)	0.6354 (2)	1.4489 (3)	0.0877 (9)	0.478 (5)
Cl3	0.7464 (5)	0.72058 (6)	1.31137 (11)	0.0718 (8)	0.478 (5)
Cl1'	0.7252 (7)	0.5906 (2)	1.2724 (3)	0.0838 (10)	0.522 (5)
Cl2'	0.8644 (6)	0.63370 (14)	1.4441 (2)	0.1015 (12)	0.522 (5)
Cl3'	0.8354 (4)	0.71700 (8)	1.30123 (8)	0.0640 (4)	0.522 (5)
C29'	0.7290 (6)	0.65719 (17)	1.3448 (2)	0.0557 (10)	0.522 (5)
H29'	0.6178	0.6701	1.3559	0.067*	0.522 (5)
O1	0.20448 (12)	0.62134 (4)	0.86461 (7)	0.0458 (2)
O2	0.37739 (12)	0.64726 (5)	0.68945 (6)	0.0451 (2)
O3	0.47972 (15)	0.69449 (5)	1.02209 (6)	0.0588 (3)
O4	0.10068 (14)	0.75164 (5)	0.58373 (6)	0.0550 (3)
O5	0.87057 (12)	0.47605 (5)	0.89164 (8)	0.0550 (3)
O6	−0.29654 (12)	0.50568 (5)	0.60580 (7)	0.0505 (3)
C1	0.36050 (16)	0.71245 (6)	0.87968 (9)	0.0390 (3)
C2	0.42348 (18)	0.73704 (7)	0.95995 (9)	0.0447 (3)
C3	0.41933 (19)	0.80154 (7)	0.97694 (10)	0.0515 (4)
H3	0.4636	0.8175	1.0324	0.062*
C4	0.35117 (19)	0.84034 (7)	0.91280 (10)	0.0502 (4)
H4	0.3462	0.8837	0.9245	0.060*
C5	0.28728 (17)	0.81810 (6)	0.82908 (10)	0.0438 (3)
C6	0.22155 (19)	0.85978 (7)	0.76273 (11)	0.0501 (4)
H6	0.2223	0.9032	0.7748	0.060*
C7	0.15732 (19)	0.83947 (7)	0.68225 (10)	0.0497 (4)
H7	0.1129	0.8683	0.6387	0.060*
C8	0.15723 (18)	0.77515 (7)	0.66393 (9)	0.0433 (3)
C9	0.22199 (16)	0.73223 (6)	0.72575 (9)	0.0382 (3)
C10	0.28973 (16)	0.75288 (6)	0.81102 (9)	0.0375 (3)
C11	0.34302 (17)	0.64259 (6)	0.87375 (8)	0.0386 (3)
C12	0.48719 (17)	0.60144 (6)	0.87996 (8)	0.0384 (3)
C13	0.64446 (17)	0.62349 (6)	0.87923 (9)	0.0423 (3)
H13	0.6620	0.6671	0.8765	0.051*
C14	0.77667 (17)	0.58352 (6)	0.88242 (9)	0.0419 (3)
H14	0.8834	0.5995	0.8812	0.050*
C15	0.75081 (17)	0.51999 (6)	0.88745 (9)	0.0427 (3)
C16	0.59450 (19)	0.49700 (7)	0.88921 (12)	0.0541 (4)
H16	0.5775	0.4534	0.8935	0.065*
C17	0.46492 (19)	0.53710 (7)	0.88481 (11)	0.0499 (4)
H17	0.3582	0.5209	0.8850	0.060*
C18	0.23968 (17)	0.66618 (6)	0.69476 (8)	0.0381 (3)
C19	0.09406 (16)	0.62645 (6)	0.67084 (8)	0.0379 (3)
C20	−0.06117 (17)	0.64490 (6)	0.68346 (9)	0.0409 (3)
H20	−0.0758	0.6851	0.7065	0.049*
C21	−0.19562 (17)	0.60641 (6)	0.66341 (9)	0.0411 (3)
H21	−0.3008	0.6198	0.6731	0.049*
C22	−0.17404 (17)	0.54777 (6)	0.62890 (9)	0.0398 (3)
C23	−0.01928 (18)	0.52839 (7)	0.61557 (10)	0.0482 (4)
H23	−0.0047	0.4883	0.5921	0.058*
C24	0.11261 (18)	0.56729 (7)	0.63632 (10)	0.0457 (3)
H24	0.2179	0.5537	0.6270	0.055*
C25	0.5735 (2)	0.71604 (9)	1.10090 (11)	0.0643 (5)
H25A	0.5032	0.7400	1.1343	0.077*
H25B	0.6624	0.7427	1.0871	0.077*
H25C	0.6194	0.6803	1.1354	0.077*
C26	0.0351 (2)	0.79353 (9)	0.51653 (11)	0.0641 (5)
H26A	0.1155	0.8261	0.5102	0.077*
H26B	−0.0645	0.8127	0.5316	0.077*
H26C	0.0093	0.7707	0.4616	0.077*
C27	1.03147 (19)	0.49649 (8)	0.88276 (13)	0.0560 (4)
H27A	1.0710	0.5251	0.9303	0.067*
H27B	1.0292	0.5179	0.8269	0.067*
H27C	1.1045	0.4604	0.8850	0.067*
C28	−0.45787 (18)	0.52379 (8)	0.61699 (12)	0.0555 (4)
H28A	−0.4892	0.5611	0.5823	0.067*
H28B	−0.4612	0.5328	0.6785	0.067*
H28C	−0.5341	0.4899	0.5978	0.067*

	U11	U22	U33	U12	U13	U23
C29	0.063 (3)	0.065 (2)	0.051 (2)	0.0107 (19)	0.0063 (18)	−0.0035 (16)
Cl1	0.1159 (17)	0.062 (2)	0.091 (2)	−0.0248 (15)	0.0161 (12)	0.0046 (14)
Cl2	0.0914 (12)	0.124 (2)	0.0476 (9)	0.0204 (10)	0.0102 (7)	0.0316 (10)
Cl3	0.112 (2)	0.0424 (5)	0.0544 (6)	0.0055 (7)	−0.0110 (8)	0.0000 (4)
Cl1'	0.141 (3)	0.0423 (13)	0.0614 (10)	0.0083 (14)	−0.0076 (14)	−0.0034 (8)
Cl2'	0.179 (3)	0.0723 (11)	0.0468 (8)	0.0443 (15)	−0.0057 (15)	0.0061 (7)
Cl3'	0.0718 (11)	0.0636 (6)	0.0553 (5)	−0.0131 (6)	0.0053 (5)	0.0089 (4)
C29'	0.057 (3)	0.061 (2)	0.0502 (17)	0.0037 (17)	0.0137 (15)	0.0103 (14)
O1	0.0442 (6)	0.0391 (5)	0.0528 (6)	−0.0031 (4)	0.0031 (4)	0.0031 (4)
O2	0.0432 (6)	0.0435 (5)	0.0480 (5)	0.0026 (4)	0.0045 (4)	−0.0020 (4)
O3	0.0831 (8)	0.0482 (6)	0.0394 (5)	0.0039 (5)	−0.0101 (5)	−0.0024 (4)
O4	0.0731 (7)	0.0468 (6)	0.0411 (5)	0.0015 (5)	−0.0047 (5)	0.0081 (4)
O5	0.0428 (6)	0.0337 (5)	0.0893 (8)	−0.0004 (4)	0.0123 (5)	−0.0042 (5)
O6	0.0427 (6)	0.0380 (5)	0.0697 (7)	−0.0029 (4)	0.0048 (5)	−0.0082 (5)
C1	0.0404 (7)	0.0348 (7)	0.0411 (7)	−0.0010 (5)	0.0034 (5)	−0.0018 (5)
C2	0.0496 (8)	0.0418 (7)	0.0412 (7)	−0.0005 (6)	0.0018 (6)	−0.0010 (6)
C3	0.0581 (9)	0.0462 (8)	0.0482 (8)	−0.0056 (7)	0.0014 (7)	−0.0112 (7)
C4	0.0571 (9)	0.0341 (7)	0.0588 (9)	−0.0040 (6)	0.0069 (7)	−0.0082 (6)
C5	0.0438 (8)	0.0340 (7)	0.0532 (8)	−0.0024 (6)	0.0059 (6)	−0.0010 (6)
C6	0.0540 (9)	0.0300 (7)	0.0657 (10)	−0.0004 (6)	0.0062 (7)	0.0030 (6)
C7	0.0537 (9)	0.0360 (7)	0.0578 (9)	0.0019 (6)	0.0032 (7)	0.0117 (6)
C8	0.0444 (8)	0.0406 (7)	0.0439 (7)	−0.0011 (6)	0.0032 (6)	0.0055 (6)
C9	0.0394 (7)	0.0331 (7)	0.0419 (7)	−0.0020 (5)	0.0048 (5)	0.0019 (5)
C10	0.0363 (7)	0.0338 (7)	0.0423 (7)	−0.0018 (5)	0.0053 (5)	0.0000 (5)
C11	0.0457 (8)	0.0365 (7)	0.0325 (6)	−0.0017 (6)	0.0022 (5)	0.0017 (5)
C12	0.0450 (8)	0.0332 (6)	0.0358 (6)	−0.0026 (6)	0.0015 (5)	0.0006 (5)
C13	0.0493 (8)	0.0304 (6)	0.0455 (7)	−0.0033 (6)	0.0015 (6)	0.0019 (5)
C14	0.0416 (8)	0.0367 (7)	0.0463 (7)	−0.0055 (6)	0.0028 (6)	−0.0002 (6)
C15	0.0443 (8)	0.0344 (7)	0.0486 (8)	0.0002 (6)	0.0048 (6)	−0.0030 (6)
C16	0.0489 (9)	0.0300 (7)	0.0839 (11)	−0.0046 (6)	0.0114 (8)	0.0001 (7)
C17	0.0433 (8)	0.0369 (7)	0.0701 (10)	−0.0049 (6)	0.0096 (7)	0.0012 (7)
C18	0.0437 (8)	0.0369 (7)	0.0329 (6)	0.0018 (6)	0.0033 (5)	0.0032 (5)
C19	0.0419 (8)	0.0358 (7)	0.0349 (6)	0.0013 (5)	0.0018 (5)	0.0015 (5)
C20	0.0475 (8)	0.0331 (6)	0.0416 (7)	0.0041 (6)	0.0048 (6)	−0.0037 (5)
C21	0.0419 (8)	0.0391 (7)	0.0421 (7)	0.0035 (6)	0.0051 (6)	−0.0009 (6)
C22	0.0436 (8)	0.0344 (7)	0.0403 (7)	−0.0008 (6)	0.0019 (5)	0.0019 (5)
C23	0.0485 (9)	0.0349 (7)	0.0604 (9)	0.0022 (6)	0.0056 (7)	−0.0102 (6)
C24	0.0420 (8)	0.0396 (7)	0.0550 (8)	0.0048 (6)	0.0056 (6)	−0.0053 (6)
C25	0.0759 (12)	0.0688 (11)	0.0424 (8)	0.0096 (9)	−0.0110 (8)	−0.0070 (8)
C26	0.0756 (12)	0.0637 (10)	0.0486 (9)	0.0055 (9)	−0.0050 (8)	0.0185 (8)
C27	0.0432 (9)	0.0447 (8)	0.0808 (11)	−0.0007 (6)	0.0118 (8)	−0.0036 (8)
C28	0.0440 (9)	0.0486 (9)	0.0738 (11)	−0.0047 (7)	0.0081 (7)	−0.0076 (8)

C29—Cl1	1.751 (7)	C11—C12	1.4769 (19)
C29—Cl3	1.761 (5)	C12—C13	1.387 (2)
C29—Cl2	1.824 (6)	C12—C17	1.3975 (19)
C29—H29	1.0000	C13—C14	1.386 (2)
Cl1'—C29'	1.816 (6)	C13—H13	0.9500
Cl2'—C29'	1.840 (6)	C14—C15	1.3852 (19)
Cl3'—C29'	1.749 (4)	C14—H14	0.9500
C29'—H29'	1.0000	C15—C16	1.389 (2)
O1—C11	1.2230 (17)	C16—C17	1.369 (2)
O2—C18	1.2243 (16)	C16—H16	0.9500
O3—C2	1.3608 (17)	C17—H17	0.9500
O3—C25	1.4273 (18)	C18—C19	1.4791 (19)
O4—C8	1.3621 (17)	C19—C20	1.3859 (19)
O4—C26	1.4238 (18)	C19—C24	1.3964 (19)
O5—C15	1.3633 (17)	C20—C21	1.385 (2)
O5—C27	1.4282 (18)	C20—H20	0.9500
O6—C22	1.3665 (16)	C21—C22	1.3906 (19)
O6—C28	1.4260 (18)	C21—H21	0.9500
C1—C2	1.3839 (19)	C22—C23	1.391 (2)
C1—C10	1.4323 (18)	C23—C24	1.375 (2)
C1—C11	1.5087 (19)	C23—H23	0.9500
C2—C3	1.412 (2)	C24—H24	0.9500
C3—C4	1.357 (2)	C25—H25A	0.9800
C3—H3	0.9500	C25—H25B	0.9800
C4—C5	1.414 (2)	C25—H25C	0.9800
C4—H4	0.9500	C26—H26A	0.9800
C5—C6	1.413 (2)	C26—H26B	0.9800
C5—C10	1.4291 (19)	C26—H26C	0.9800
C6—C7	1.357 (2)	C27—H27A	0.9800
C6—H6	0.9500	C27—H27B	0.9800
C7—C8	1.410 (2)	C27—H27C	0.9800
C7—H7	0.9500	C28—H28A	0.9800
C8—C9	1.3814 (19)	C28—H28B	0.9800
C9—C10	1.4311 (18)	C28—H28C	0.9800
C9—C18	1.5122 (18)
Cl1—C29—Cl3	106.7 (4)	C15—C14—H14	120.5
Cl1—C29—Cl2	104.4 (3)	C13—C14—H14	120.5
Cl3—C29—Cl2	103.2 (3)	O5—C15—C14	124.55 (13)
Cl1—C29—H29	113.8	O5—C15—C16	115.23 (12)
Cl3—C29—H29	113.8	C14—C15—C16	120.22 (13)
Cl2—C29—H29	113.8	C17—C16—C15	120.05 (13)
Cl3'—C29'—Cl1'	107.6 (3)	C17—C16—H16	120.0
Cl3'—C29'—Cl2'	104.3 (3)	C15—C16—H16	120.0
Cl1'—C29'—Cl2'	104.8 (3)	C16—C17—C12	121.05 (14)
Cl3'—C29'—H29'	113.1	C16—C17—H17	119.5
Cl1'—C29'—H29'	113.1	C12—C17—H17	119.5
Cl2'—C29'—H29'	113.1	O2—C18—C19	121.62 (12)
C2—O3—C25	118.50 (13)	O2—C18—C9	117.87 (12)
C8—O4—C26	118.65 (13)	C19—C18—C9	120.51 (12)
C15—O5—C27	117.69 (11)	C20—C19—C24	118.10 (13)
C22—O6—C28	117.37 (11)	C20—C19—C18	122.55 (12)
C2—C1—C10	119.91 (12)	C24—C19—C18	119.33 (13)
C2—C1—C11	117.03 (12)	C21—C20—C19	121.93 (12)
C10—C1—C11	122.17 (12)	C21—C20—H20	119.0
O3—C2—C1	115.31 (12)	C19—C20—H20	119.0
O3—C2—C3	122.79 (13)	C20—C21—C22	118.88 (13)
C1—C2—C3	121.78 (13)	C20—C21—H21	120.6
C4—C3—C2	118.97 (14)	C22—C21—H21	120.6
C4—C3—H3	120.5	O6—C22—C21	124.61 (13)
C2—C3—H3	120.5	O6—C22—C23	115.29 (12)
C3—C4—C5	121.83 (14)	C21—C22—C23	120.10 (13)
C3—C4—H4	119.1	C24—C23—C22	120.02 (13)
C5—C4—H4	119.1	C24—C23—H23	120.0
C6—C5—C4	120.62 (13)	C22—C23—H23	120.0
C6—C5—C10	119.53 (13)	C23—C24—C19	120.97 (14)
C4—C5—C10	119.85 (13)	C23—C24—H24	119.5
C7—C6—C5	121.71 (14)	C19—C24—H24	119.5
C7—C6—H6	119.1	O3—C25—H25A	109.5
C5—C6—H6	119.1	O3—C25—H25B	109.5
C6—C7—C8	119.29 (13)	H25A—C25—H25B	109.5
C6—C7—H7	120.4	O3—C25—H25C	109.5
C8—C7—H7	120.4	H25A—C25—H25C	109.5
O4—C8—C9	115.78 (12)	H25B—C25—H25C	109.5
O4—C8—C7	122.51 (13)	O4—C26—H26A	109.5
C9—C8—C7	121.64 (13)	O4—C26—H26B	109.5
C8—C9—C10	119.75 (12)	H26A—C26—H26B	109.5
C8—C9—C18	116.77 (12)	O4—C26—H26C	109.5
C10—C9—C18	122.85 (11)	H26A—C26—H26C	109.5
C5—C10—C9	118.06 (12)	H26B—C26—H26C	109.5
C5—C10—C1	117.65 (12)	O5—C27—H27A	109.5
C9—C10—C1	124.29 (12)	O5—C27—H27B	109.5
O1—C11—C12	121.28 (12)	H27A—C27—H27B	109.5
O1—C11—C1	117.27 (12)	O5—C27—H27C	109.5
C12—C11—C1	121.45 (12)	H27A—C27—H27C	109.5
C13—C12—C17	118.00 (13)	H27B—C27—H27C	109.5
C13—C12—C11	123.07 (12)	O6—C28—H28A	109.5
C17—C12—C11	118.91 (13)	O6—C28—H28B	109.5
C14—C13—C12	121.69 (12)	H28A—C28—H28B	109.5
C14—C13—H13	119.2	O6—C28—H28C	109.5
C12—C13—H13	119.2	H28A—C28—H28C	109.5
C15—C14—C13	118.97 (13)	H28B—C28—H28C	109.5
C25—O3—C2—C1	168.44 (14)	C10—C1—C11—C12	121.00 (14)
C25—O3—C2—C3	−15.5 (2)	O1—C11—C12—C13	171.55 (13)
C10—C1—C2—O3	176.54 (12)	C1—C11—C12—C13	−9.31 (19)
C11—C1—C2—O3	7.2 (2)	O1—C11—C12—C17	−6.9 (2)
C10—C1—C2—C3	0.4 (2)	C1—C11—C12—C17	172.21 (13)
C11—C1—C2—C3	−168.95 (14)	C17—C12—C13—C14	0.5 (2)
O3—C2—C3—C4	−175.58 (15)	C11—C12—C13—C14	−177.95 (12)
C1—C2—C3—C4	0.2 (2)	C12—C13—C14—C15	−0.7 (2)
C2—C3—C4—C5	−1.3 (2)	C27—O5—C15—C14	−5.6 (2)
C3—C4—C5—C6	−178.04 (14)	C27—O5—C15—C16	174.88 (14)
C3—C4—C5—C10	1.7 (2)	C13—C14—C15—O5	−179.46 (13)
C4—C5—C6—C7	−179.00 (15)	C13—C14—C15—C16	0.0 (2)
C10—C5—C6—C7	1.3 (2)	O5—C15—C16—C17	−179.60 (15)
C5—C6—C7—C8	−0.5 (2)	C14—C15—C16—C17	0.9 (2)
C26—O4—C8—C9	−178.84 (14)	C15—C16—C17—C12	−1.1 (3)
C26—O4—C8—C7	−1.7 (2)	C13—C12—C17—C16	0.4 (2)
C6—C7—C8—O4	−177.39 (14)	C11—C12—C17—C16	178.92 (15)
C6—C7—C8—C9	−0.5 (2)	C8—C9—C18—O2	107.25 (15)
O4—C8—C9—C10	177.78 (12)	C10—C9—C18—O2	−63.58 (17)
C7—C8—C9—C10	0.6 (2)	C8—C9—C18—C19	−72.04 (17)
O4—C8—C9—C18	6.65 (19)	C10—C9—C18—C19	117.13 (14)
C7—C8—C9—C18	−170.49 (13)	O2—C18—C19—C20	174.23 (12)
C6—C5—C10—C9	−1.1 (2)	C9—C18—C19—C20	−6.50 (19)
C4—C5—C10—C9	179.24 (13)	O2—C18—C19—C24	−3.99 (19)
C6—C5—C10—C1	178.76 (13)	C9—C18—C19—C24	175.27 (12)
C4—C5—C10—C1	−0.9 (2)	C24—C19—C20—C21	0.4 (2)
C8—C9—C10—C5	0.1 (2)	C18—C19—C20—C21	−177.84 (12)
C18—C9—C10—C5	170.69 (13)	C19—C20—C21—C22	−0.6 (2)
C8—C9—C10—C1	−179.69 (13)	C28—O6—C22—C21	0.9 (2)
C18—C9—C10—C1	−9.1 (2)	C28—O6—C22—C23	−179.05 (14)
C2—C1—C10—C5	−0.1 (2)	C20—C21—C22—O6	−179.47 (13)
C11—C1—C10—C5	168.75 (13)	C20—C21—C22—C23	0.4 (2)
C2—C1—C10—C9	179.75 (13)	O6—C22—C23—C24	179.76 (14)
C11—C1—C10—C9	−11.4 (2)	C21—C22—C23—C24	−0.2 (2)
C2—C1—C11—O1	109.29 (15)	C22—C23—C24—C19	0.0 (2)
C10—C1—C11—O1	−59.83 (18)	C20—C19—C24—C23	−0.1 (2)
C2—C1—C11—C12	−69.88 (17)	C18—C19—C24—C23	178.19 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O5i	0.95	2.37	3.1460 (19)	139
C13—H13···Cl3ii	0.95	2.75	3.647 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O5i	0.95	2.37	3.1460 (19)	139
C13—H13⋯Cl3ii	0.95	2.75	3.647 (2)	159

Symmetry codes: (i) ; (ii) .