[8-(4-Chloro­benzo­yl)-2,7-dimeth­oxy­naphthalen-1-yl](2,4,6-trimethyl­phen­yl)methanone

Muto, T.; Sasagawa, K.; Okamoto, A.; Oike, H.; Yonezawa, N.

doi:10.1107/S1600536812008112

[8-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalen-1-yl](2,4,6-trimethylphenyl)methanone

T. Muto, K. Sasagawa, A. Okamoto, H. Oike and N. Yonezawa

In the title compound, C₂₉H₂₅ClO₄, the dihedral angle between the benzene rings of the 2,4,6-trimethylbenzoyl group and the 4-chlorobenzoyl group is 65.19 (9)°. The dihedral angles between the naphthalene ring system and the benzene rings of the 2,4,6-trimethylbenzoyl group and the 4-chlorobenzoyl group are 85.66 (8) and 69.48 (8)°, respectively. In the crystal, two types of intermolecular C—H

O interactions and an intramolecular C—H

O interaction are observed. Moreover, there is a short intramolecular C=O

C=O contact of 2.614 (2) Å between the benzoyl substituents.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812008112/gk2460sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812008112/gk2460Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812008112/gk2460Isup3.cml Supplementary material

CCDC reference: 872633

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Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.131
Data-to-parameter ratio = 13.6

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Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009; Okamoto, Mitsui et al., 2011). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene analogues exemplified by 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007) and 1,8-bis(2,4,6-trimethylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., 2012). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are connected to the naphthalene rings in an almost perpendicular fashion. Besides, the crystal structures of 1-monoaroylated naphthalene derivatives and the β-isomers of 3-monoaroylated derivatives have been also clarified such as 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al., 2008), (2,7-dimethoxynaphthalen-1-yl)(2,4,6-trimethylphenyl)methanone (Muto et al., 2011a) and (3,6-dimethoxynaphthalen-2-yl)(2,4,6-trimethylphenyl)methanone (Muto et al., 2011b).

As a part of our continuing study on the molecular structures of these homologous molecules, the crystal structure of title compound, unsymmetrical peri-substituted naphthalene bearing 2,4,6-trimethylbenzoyl group and 4-chlorobenzoyl group, is discussed in this report.

The molecular structure of the title compound is displayed in Fig. 1. The 2,4,6-trimethylphenyl group and 4-chlorophenyl group are out of the plane of the naphthalene ring. Two kinds of phenyl rings make different dihedral angles with the naphthalene ring system, i.e., the dihedral angle between the best planes of the 2,4,6-trimethylphenyl ring (C12—C17) and the naphthalene ring (C1—C10) is 85.66 (8)°, whereas, that between the best planes of the 4-chlorophenyl ring (C19—C24) and the naphthalene ring (C1—C10) is 69.48 (8)°. Each of dihedral angles is similar to that of the corresponding symmetric 1,8-diaroylnaphthalene. The dihedral angles between the best planes of the 2,4,6-trimethylphenyl rings and the naphthalene ring of 1,8-bis(2,4,6-trimethylbenzoyl)-2,7-dimethoxynaphthalene are 81.58 (5) and 84.92 (6)° (Muto et al., 2012). In addition, the dihedral angles between the best planes of the 4-chlorophenyl rings and the naphthalene ring of 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene are 71.55 (7) and 71.98 (7)° (Nakaema et al., 2007).

Besides, an intramolecular C—H···O interaction between methyl group and carbonyl group is observed (C29—H29b···O2 = 2.42 Å; Fig. 1 and Table 1).

The crystal packing is additionally stabilized by an intermolecular C—H···O interaction between the oxygen atom (O2) of the carbonyl group and one hydrogen atom (H23) on 4-chlorophenyl group of the adjacent molecule along the b axis (C23—H23···O2ⁱ; Fig. 2 and Table 1). Furthermore, an intermolecular C—H···O hydrogen bonding between the oxygen atom (O1) of the carbonyl group and one hydrogen atom (H28a) of the 4-methyl group on 2,4,6-trimethylphenyl ring of the adjacent molecule along the b axis is observed (C28—H28a···O1 ⁱⁱ; Fig. 3 and Table 1).

Related literature top

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Mitsui et al. (2008); Muto et al. (2011a,b, 2012); Nakaema et al. (2007).

Experimental top

To a 10 ml flask, 4-chlorobenzoyl chloride (0.40 mmol, 0.070 g), titanium chloride (1.20 mmol, 0.228 g) and methylene chloride (0.50 ml) were placed and stirred at rt. To the reaction mixture thus obtained, 1-(2,4,6-trimethylbenzoyl)-2,7-dimethoxynaphthalene (0.20 mmol, 0.067 g) was added. After the reaction mixture was stirred at rt for 9 h, it was poured into ice-cold water (10 ml). The aqueous layer was extracted with CHCl₃ (10 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake (quant.). The crude product was purified by recrystallization from hexane and CHCl₃ (yield 2%).

¹H NMR δ (300 MHz, CDCl₃); 2.16 (6H, s), 2.25 (3H, s), 3.47 (3H, s), 3.68 (3H, s), 6.77 (2H, s), 7.10 (1H, d, J = 9.0 Hz), 7.23 (1H, d, J = 9.3 Hz), 7.34 (2H, d, J = 8.7 Hz), 7.74 (2H, d, J = 8.7 Hz), 7.92 (1H, d, J = 8.7 Hz), 7.94 (1H, d, J = 9.0 Hz) p.p.m..

¹³C NMR δ (125 MHz, CDCl₃); 21.11, 21.35, 56.27, 56.83, 111.13, 112.39, 121.13, 124.87, 125.72, 128.13, 129.26, 129.57, 130.13, 132.43, 133.27, 137.88, 138.37, 138.57, 139.21, 157.20, 157.94, 195.83, 199.69 p.p.m..

IR (KBr); 1656 (C=O), 1607, 1514, 1457(Ar, naphthalene), 1271 (=C—O—C) cm^-1.

HRMS (m/z); [M + Na]⁺ Calcd for C₂₉H₂₅ClO₄Na, 495.1370; found, 495.1339.

m.p. = 503.0–505.0 K.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure with displacement ellipsoids at 50% probability and a weak intramolecular C—H···O interactions.
	Fig. 2. Intermolecular C23—H23···O2ⁱ interactions, viewed along the c axis [symmetry code: (i) –x + 1, y + 1/2, -z + 1/2].
	Fig. 3. A packing diagram of the title compound, showing intermolecular C28—H28a···O1 ⁱⁱ interactions [symmetry code: (ii) –x, y - 1/2, -z + 1/2].

[8-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalen-1-yl](2,4,6- trimethylphenyl)methanone top

Crystal data top

C₂₉H₂₅ClO₄	F(000) = 992
M_r = 472.94	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 30848 reflections
a = 11.6017 (2) Å	θ = 3.6–68.2°
b = 12.3381 (2) Å	µ = 1.73 mm⁻¹
c = 16.2825 (3) Å	T = 193 K
β = 90.503 (1)°	Block, colorless
V = 2330.64 (7) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4266 independent reflections
Radiation source: rotating anode	3197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.8°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −14→14
T_min = 0.625, T_max = 0.846	l = −19→19
40504 measured reflections

Refinement top

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0647P)² + 0.4811P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
4266 reflections	Δρ_max = 0.21 e Å⁻³
313 parameters	Δρ_min = −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: 0.0019 (2)

Crystal data top

C₂₉H₂₅ClO₄	V = 2330.64 (7) Å³
M_r = 472.94	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.6017 (2) Å	µ = 1.73 mm⁻¹
b = 12.3381 (2) Å	T = 193 K
c = 16.2825 (3) Å	0.30 × 0.20 × 0.10 mm
β = 90.503 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4266 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3197 reflections with I > 2σ(I)
T_min = 0.625, T_max = 0.846	R_int = 0.054
40504 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.15	Δρ_max = 0.21 e Å⁻³
4266 reflections	Δρ_min = −0.24 e Å⁻³
313 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

	x	y	z	U_iso*/U_eq
Cl1	0.69235 (5)	0.10716 (5)	0.47771 (3)	0.0588 (2)
O1	0.20277 (12)	0.08172 (12)	0.27478 (9)	0.0481 (4)
O2	0.33992 (13)	−0.06714 (11)	0.17961 (9)	0.0507 (4)
O3	−0.02500 (13)	0.23149 (13)	0.17441 (10)	0.0584 (4)
O4	0.55327 (12)	0.05151 (12)	0.09221 (9)	0.0492 (4)
C1	0.15846 (17)	0.16470 (15)	0.14692 (12)	0.0393 (5)
C2	0.06994 (18)	0.23511 (17)	0.12574 (13)	0.0454 (5)
C3	0.07890 (19)	0.30891 (17)	0.06063 (13)	0.0489 (5)
H3	0.0164	0.3555	0.0470	0.059*
C4	0.17854 (19)	0.31268 (17)	0.01738 (13)	0.0480 (5)
H4	0.1846	0.3618	−0.0273	0.058*
C5	0.27304 (18)	0.24567 (15)	0.03717 (12)	0.0411 (5)
C6	0.37374 (19)	0.25238 (17)	−0.01035 (12)	0.0453 (5)
H6	0.3761	0.3020	−0.0549	0.054*
C7	0.46715 (18)	0.19001 (17)	0.00576 (12)	0.0459 (5)
H7	0.5338	0.1948	−0.0275	0.055*
C8	0.46389 (17)	0.11829 (16)	0.07222 (12)	0.0416 (5)
C9	0.36732 (17)	0.10735 (15)	0.12160 (12)	0.0379 (4)
C10	0.26600 (17)	0.17072 (15)	0.10417 (12)	0.0382 (4)
C11	0.13588 (17)	0.08802 (15)	0.21667 (13)	0.0402 (5)
C12	0.02723 (16)	0.02178 (15)	0.21450 (12)	0.0389 (4)
C13	−0.05043 (17)	0.03204 (16)	0.28009 (12)	0.0424 (5)
C14	−0.15272 (17)	−0.02578 (16)	0.27704 (12)	0.0436 (5)
H14	−0.2059	−0.0179	0.3207	0.052*
C15	−0.18025 (17)	−0.09461 (16)	0.21268 (13)	0.0414 (5)
C16	−0.10099 (17)	−0.10558 (16)	0.14962 (13)	0.0421 (5)
H16	−0.1179	−0.1536	0.1055	0.050*
C17	0.00221 (17)	−0.04836 (16)	0.14928 (12)	0.0404 (5)
C18	0.38091 (16)	0.02322 (15)	0.18818 (12)	0.0394 (5)
C19	0.45487 (16)	0.04930 (15)	0.26164 (12)	0.0388 (4)
C20	0.46449 (18)	−0.02682 (16)	0.32407 (12)	0.0449 (5)
H20	0.4207	−0.0918	0.3211	0.054*
C21	0.53713 (18)	−0.00905 (17)	0.39053 (13)	0.0476 (5)
H21	0.5439	−0.0617	0.4329	0.057*
C22	0.59999 (17)	0.08638 (17)	0.39460 (13)	0.0446 (5)
C23	0.59021 (17)	0.16476 (17)	0.33401 (12)	0.0442 (5)
H23	0.6331	0.2302	0.3376	0.053*
C24	0.51680 (17)	0.14576 (16)	0.26821 (12)	0.0416 (5)
H24	0.5084	0.1994	0.2267	0.050*
C25	−0.1238 (2)	0.2937 (2)	0.15477 (17)	0.0650 (7)
H25A	−0.1048	0.3710	0.1584	0.078*
H25B	−0.1854	0.2768	0.1935	0.078*
H25C	−0.1496	0.2765	0.0988	0.078*
C26	0.66420 (18)	0.0740 (2)	0.05727 (15)	0.0569 (6)
H26A	0.6843	0.1501	0.0671	0.068*
H26B	0.6614	0.0602	−0.0020	0.068*
H26C	0.7224	0.0272	0.0829	0.068*
C27	−0.0277 (2)	0.1066 (2)	0.35151 (15)	0.0607 (6)
H27A	−0.0005	0.1767	0.3312	0.073*
H27B	0.0312	0.0746	0.3876	0.073*
H27C	−0.0990	0.1170	0.3823	0.073*
C28	−0.29352 (17)	−0.15531 (17)	0.21101 (14)	0.0465 (5)
H28A	−0.2807	−0.2295	0.1916	0.056*
H28B	−0.3477	−0.1185	0.1739	0.056*
H28C	−0.3256	−0.1573	0.2665	0.056*
C29	0.08631 (19)	−0.06858 (19)	0.07974 (14)	0.0513 (5)
H29A	0.0572	−0.1274	0.0448	0.062*
H29B	0.1616	−0.0889	0.1027	0.062*
H29C	0.0942	−0.0025	0.0469	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0508 (3)	0.0793 (4)	0.0463 (3)	0.0077 (3)	−0.0052 (3)	−0.0046 (3)
O1	0.0416 (8)	0.0590 (9)	0.0436 (9)	−0.0052 (7)	−0.0041 (7)	0.0070 (7)
O2	0.0572 (9)	0.0425 (8)	0.0525 (9)	−0.0051 (7)	−0.0018 (7)	0.0016 (6)
O3	0.0450 (8)	0.0610 (10)	0.0693 (11)	0.0130 (7)	0.0078 (8)	0.0100 (8)
O4	0.0459 (8)	0.0531 (8)	0.0487 (9)	0.0059 (7)	0.0125 (7)	0.0070 (7)
C1	0.0413 (11)	0.0385 (10)	0.0381 (11)	−0.0018 (8)	−0.0014 (9)	−0.0014 (8)
C2	0.0439 (11)	0.0458 (11)	0.0464 (12)	0.0012 (9)	−0.0032 (10)	−0.0028 (9)
C3	0.0529 (13)	0.0435 (11)	0.0502 (13)	0.0031 (10)	−0.0098 (10)	0.0025 (9)
C4	0.0599 (14)	0.0418 (11)	0.0421 (12)	−0.0030 (10)	−0.0105 (10)	0.0039 (9)
C5	0.0487 (11)	0.0386 (10)	0.0360 (11)	−0.0062 (9)	−0.0068 (9)	−0.0005 (8)
C6	0.0552 (13)	0.0460 (11)	0.0346 (11)	−0.0099 (10)	−0.0017 (9)	0.0028 (9)
C7	0.0501 (12)	0.0498 (12)	0.0380 (11)	−0.0078 (10)	0.0043 (9)	−0.0002 (9)
C8	0.0456 (11)	0.0418 (11)	0.0375 (11)	−0.0019 (9)	0.0019 (9)	−0.0014 (8)
C9	0.0410 (10)	0.0393 (10)	0.0336 (10)	−0.0020 (8)	0.0020 (8)	−0.0001 (8)
C10	0.0439 (11)	0.0362 (10)	0.0345 (10)	−0.0054 (8)	−0.0036 (8)	−0.0023 (8)
C11	0.0393 (11)	0.0408 (10)	0.0405 (12)	0.0016 (8)	0.0024 (9)	−0.0011 (8)
C12	0.0370 (10)	0.0415 (10)	0.0381 (11)	0.0017 (8)	−0.0005 (8)	0.0014 (8)
C13	0.0436 (11)	0.0451 (11)	0.0384 (11)	−0.0003 (9)	0.0027 (9)	−0.0040 (9)
C14	0.0419 (11)	0.0477 (11)	0.0414 (11)	−0.0003 (9)	0.0054 (9)	0.0010 (9)
C15	0.0380 (11)	0.0413 (11)	0.0449 (12)	0.0024 (8)	−0.0031 (9)	0.0036 (9)
C16	0.0429 (11)	0.0429 (11)	0.0404 (11)	0.0016 (9)	−0.0041 (9)	−0.0031 (9)
C17	0.0414 (11)	0.0433 (10)	0.0366 (11)	0.0032 (8)	0.0010 (9)	0.0012 (8)
C18	0.0375 (10)	0.0388 (10)	0.0419 (11)	0.0021 (8)	0.0061 (9)	0.0003 (8)
C19	0.0372 (10)	0.0410 (10)	0.0382 (11)	0.0038 (8)	0.0063 (8)	0.0013 (8)
C20	0.0496 (12)	0.0416 (11)	0.0437 (12)	0.0002 (9)	0.0054 (10)	0.0058 (9)
C21	0.0534 (12)	0.0499 (12)	0.0394 (12)	0.0087 (10)	0.0028 (10)	0.0069 (9)
C22	0.0404 (11)	0.0547 (12)	0.0387 (12)	0.0088 (9)	0.0043 (9)	−0.0031 (9)
C23	0.0420 (11)	0.0475 (11)	0.0431 (12)	−0.0004 (9)	0.0061 (9)	−0.0040 (9)
C24	0.0433 (11)	0.0425 (11)	0.0391 (11)	0.0034 (9)	0.0052 (9)	0.0038 (9)
C25	0.0433 (13)	0.0658 (15)	0.0857 (19)	0.0084 (11)	−0.0070 (12)	−0.0008 (13)
C26	0.0432 (12)	0.0672 (15)	0.0605 (15)	−0.0001 (10)	0.0090 (11)	0.0034 (11)
C27	0.0555 (14)	0.0743 (16)	0.0526 (14)	−0.0118 (12)	0.0093 (11)	−0.0193 (12)
C28	0.0417 (11)	0.0487 (12)	0.0491 (13)	−0.0067 (9)	−0.0024 (9)	0.0026 (9)
C29	0.0477 (12)	0.0623 (14)	0.0439 (13)	−0.0021 (10)	0.0040 (10)	−0.0099 (10)

Geometric parameters (Å, º) top

Cl1—C22	1.738 (2)	C15—C16	1.391 (3)
O1—C11	1.221 (2)	C15—C28	1.513 (3)
O2—C18	1.220 (2)	C16—C17	1.390 (3)
O3—C2	1.363 (2)	C16—H16	0.9500
O3—C25	1.414 (3)	C17—C29	1.522 (3)
O4—C8	1.362 (2)	C18—C19	1.501 (3)
O4—C26	1.439 (2)	C19—C20	1.388 (3)
C1—C2	1.386 (3)	C19—C24	1.394 (3)
C1—C10	1.436 (3)	C20—C21	1.383 (3)
C1—C11	1.503 (3)	C20—H20	0.9500
C2—C3	1.402 (3)	C21—C22	1.386 (3)
C3—C4	1.360 (3)	C21—H21	0.9500
C3—H3	0.9500	C22—C23	1.385 (3)
C4—C5	1.408 (3)	C23—C24	1.383 (3)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.409 (3)	C24—H24	0.9500
C5—C10	1.433 (3)	C25—H25A	0.9800
C6—C7	1.353 (3)	C25—H25B	0.9800
C6—H6	0.9500	C25—H25C	0.9800
C7—C8	1.399 (3)	C26—H26A	0.9800
C7—H7	0.9500	C26—H26B	0.9800
C8—C9	1.391 (3)	C26—H26C	0.9800
C9—C10	1.438 (3)	C27—H27A	0.9800
C9—C18	1.508 (3)	C27—H27B	0.9800
C11—C12	1.502 (3)	C27—H27C	0.9800
C12—C17	1.398 (3)	C28—H28A	0.9800
C12—C13	1.409 (3)	C28—H28B	0.9800
C13—C14	1.385 (3)	C28—H28C	0.9800
C13—C27	1.504 (3)	C29—H29A	0.9800
C14—C15	1.384 (3)	C29—H29B	0.9800
C14—H14	0.9500	C29—H29C	0.9800

C2—O3—C25	120.54 (18)	C12—C17—C29	122.43 (18)
C8—O4—C26	118.07 (16)	O2—C18—C19	120.45 (18)
C2—C1—C10	119.46 (18)	O2—C18—C9	120.58 (18)
C2—C1—C11	116.67 (17)	C19—C18—C9	118.73 (16)
C10—C1—C11	123.84 (17)	C20—C19—C24	118.92 (19)
O3—C2—C1	115.81 (18)	C20—C19—C18	118.71 (18)
O3—C2—C3	121.77 (19)	C24—C19—C18	122.35 (18)
C1—C2—C3	122.37 (19)	C21—C20—C19	120.7 (2)
C4—C3—C2	118.9 (2)	C21—C20—H20	119.7
C4—C3—H3	120.6	C19—C20—H20	119.7
C2—C3—H3	120.6	C20—C21—C22	119.26 (19)
C3—C4—C5	121.7 (2)	C20—C21—H21	120.4
C3—C4—H4	119.2	C22—C21—H21	120.4
C5—C4—H4	119.2	C23—C22—C21	121.3 (2)
C4—C5—C6	119.17 (19)	C23—C22—Cl1	119.84 (17)
C4—C5—C10	120.24 (18)	C21—C22—Cl1	118.89 (17)
C6—C5—C10	120.59 (19)	C24—C23—C22	118.64 (19)
C7—C6—C5	121.77 (19)	C24—C23—H23	120.7
C7—C6—H6	119.1	C22—C23—H23	120.7
C5—C6—H6	119.1	C23—C24—C19	121.19 (19)
C6—C7—C8	118.87 (19)	C23—C24—H24	119.4
C6—C7—H7	120.6	C19—C24—H24	119.4
C8—C7—H7	120.6	O3—C25—H25A	109.5
O4—C8—C9	114.75 (17)	O3—C25—H25B	109.5
O4—C8—C7	122.82 (17)	H25A—C25—H25B	109.5
C9—C8—C7	122.40 (19)	O3—C25—H25C	109.5
C8—C9—C10	119.62 (18)	H25A—C25—H25C	109.5
C8—C9—C18	113.73 (17)	H25B—C25—H25C	109.5
C10—C9—C18	126.60 (16)	O4—C26—H26A	109.5
C5—C10—C1	117.25 (18)	O4—C26—H26B	109.5
C5—C10—C9	116.69 (17)	H26A—C26—H26B	109.5
C1—C10—C9	126.05 (17)	O4—C26—H26C	109.5
O1—C11—C12	120.73 (17)	H26A—C26—H26C	109.5
O1—C11—C1	120.79 (18)	H26B—C26—H26C	109.5
C12—C11—C1	118.45 (18)	C13—C27—H27A	109.5
C17—C12—C13	120.09 (18)	C13—C27—H27B	109.5
C17—C12—C11	121.53 (17)	H27A—C27—H27B	109.5
C13—C12—C11	118.38 (17)	C13—C27—H27C	109.5
C14—C13—C12	118.68 (18)	H27A—C27—H27C	109.5
C14—C13—C27	119.13 (18)	H27B—C27—H27C	109.5
C12—C13—C27	122.15 (18)	C15—C28—H28A	109.5
C15—C14—C13	122.35 (19)	C15—C28—H28B	109.5
C15—C14—H14	118.8	H28A—C28—H28B	109.5
C13—C14—H14	118.8	C15—C28—H28C	109.5
C14—C15—C16	117.96 (18)	H28A—C28—H28C	109.5
C14—C15—C28	120.80 (18)	H28B—C28—H28C	109.5
C16—C15—C28	121.23 (19)	C17—C29—H29A	109.5
C17—C16—C15	121.92 (19)	C17—C29—H29B	109.5
C17—C16—H16	119.0	H29A—C29—H29B	109.5
C15—C16—H16	119.0	C17—C29—H29C	109.5
C16—C17—C12	118.97 (18)	H29A—C29—H29C	109.5
C16—C17—C29	118.54 (18)	H29B—C29—H29C	109.5

C25—O3—C2—C1	−175.14 (19)	O1—C11—C12—C17	−123.9 (2)
C25—O3—C2—C3	7.5 (3)	C1—C11—C12—C17	58.0 (3)
C10—C1—C2—O3	−173.78 (17)	O1—C11—C12—C13	56.4 (3)
C11—C1—C2—O3	4.2 (3)	C1—C11—C12—C13	−121.7 (2)
C10—C1—C2—C3	3.6 (3)	C17—C12—C13—C14	−2.0 (3)
C11—C1—C2—C3	−178.48 (19)	C11—C12—C13—C14	177.67 (18)
O3—C2—C3—C4	176.24 (19)	C17—C12—C13—C27	−179.8 (2)
C1—C2—C3—C4	−0.9 (3)	C11—C12—C13—C27	−0.1 (3)
C2—C3—C4—C5	−1.0 (3)	C12—C13—C14—C15	1.2 (3)
C3—C4—C5—C6	179.39 (19)	C27—C13—C14—C15	179.0 (2)
C3—C4—C5—C10	0.2 (3)	C13—C14—C15—C16	0.4 (3)
C4—C5—C6—C7	−179.97 (19)	C13—C14—C15—C28	−179.21 (19)
C10—C5—C6—C7	−0.8 (3)	C14—C15—C16—C17	−1.2 (3)
C5—C6—C7—C8	−1.0 (3)	C28—C15—C16—C17	178.41 (19)
C26—O4—C8—C9	−166.11 (18)	C15—C16—C17—C12	0.4 (3)
C26—O4—C8—C7	15.8 (3)	C15—C16—C17—C29	177.52 (19)
C6—C7—C8—O4	179.09 (18)	C13—C12—C17—C16	1.3 (3)
C6—C7—C8—C9	1.1 (3)	C11—C12—C17—C16	−178.42 (18)
O4—C8—C9—C10	−177.55 (17)	C13—C12—C17—C29	−175.75 (19)
C7—C8—C9—C10	0.6 (3)	C11—C12—C17—C29	4.5 (3)
O4—C8—C9—C18	0.2 (3)	C8—C9—C18—O2	−99.7 (2)
C7—C8—C9—C18	178.27 (18)	C10—C9—C18—O2	77.8 (3)
C4—C5—C10—C1	2.4 (3)	C8—C9—C18—C19	74.7 (2)
C6—C5—C10—C1	−176.82 (18)	C10—C9—C18—C19	−107.8 (2)
C4—C5—C10—C9	−178.44 (18)	O2—C18—C19—C20	−7.5 (3)
C6—C5—C10—C9	2.4 (3)	C9—C18—C19—C20	178.04 (17)
C2—C1—C10—C5	−4.1 (3)	O2—C18—C19—C24	170.53 (18)
C11—C1—C10—C5	178.04 (17)	C9—C18—C19—C24	−3.9 (3)
C2—C1—C10—C9	176.74 (18)	C24—C19—C20—C21	−2.1 (3)
C11—C1—C10—C9	−1.1 (3)	C18—C19—C20—C21	176.06 (17)
C8—C9—C10—C5	−2.2 (3)	C19—C20—C21—C22	0.5 (3)
C18—C9—C10—C5	−179.63 (18)	C20—C21—C22—C23	0.9 (3)
C8—C9—C10—C1	176.87 (18)	C20—C21—C22—Cl1	−179.21 (15)
C18—C9—C10—C1	−0.5 (3)	C21—C22—C23—C24	−0.6 (3)
C2—C1—C11—O1	−127.5 (2)	Cl1—C22—C23—C24	179.47 (14)
C10—C1—C11—O1	50.4 (3)	C22—C23—C24—C19	−1.0 (3)
C2—C1—C11—C12	50.6 (2)	C20—C19—C24—C23	2.3 (3)
C10—C1—C11—C12	−131.50 (19)	C18—C19—C24—C23	−175.70 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O2ⁱ	0.95	2.54	3.413 (2)	154
C28—H28A···O1ⁱⁱ	0.98	2.56	3.418 (3)	147
C29—H29B···O2	0.98	2.42	3.349 (3)	157

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₅ClO₄
M_r	472.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	11.6017 (2), 12.3381 (2), 16.2825 (3)
β (°)	90.503 (1)
V (Å³)	2330.64 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.73
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.625, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	40504, 4266, 3197
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.131, 1.15
No. of reflections	4266
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).