1,8-Bis(4-chloro­benzo­yl)-2,7-dimethoxy­naphthalene

Nakaema, K.; Okamoto, A.; Noguchi, K.; Yonezawa, N.

doi:10.1107/S1600536807045114

1,8-Bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene

K. Nakaema, A. Okamoto, K. Noguchi and N. Yonezawa

The title compound, C₂₆H₁₈Cl₂O₄, has two 4-chlorobenzoyl groups that are in an anti orientation and are approximately parallel. The interplanar angle between the mean planes of the two benzene rings is 7.99 (8)°. These 4-chlorobenzoyl groups are twisted away from the attached naphthalene ring. The two interplanar angles between the mean planes of the chlorophenyl groups and the naphthalene ring system are 71.55 (7) and 71.98 (7)°. The torsion angles between the carbonyl groups and the naphthalene ring are 64.9 (2) and 64.4 (2)°, which are far larger than those between the 4-chlorophenyl groups and the carbonyl groups of 0.0 (2) and -3.8 (3)°. The chlorophenyl and carbonyl groups are almost coplanar. Intermolecular hydrogen bonds exist between aromatic H and carbonyl O atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045114/is2207sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045114/is2207Isup2.hkl Contains datablock I

CCDC reference: 664209

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R factor = 0.028
wR factor = 0.075
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           68.18
           From the CIF: _reflns_number_total               3800
           Count of symmetry unique reflns         2100
           Completeness (_total/calc)            180.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1700
           Fraction of Friedel pairs measured     0.810
           Are heavy atom types Z>Si present        yes

Author Response: The number of Friedel pairs was checked and added to the _refine_ls_abs_structure_details line.

PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

Author Response: The restraints used in the refinement were explained in _publ_section_exptl_refinement section.


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Naphthalene derivatives, such as 1,5-disubstituted and 2,6-disubstituted naphthalenes, have been used widely as key building blocks of functional organic compounds such as liquid crystals and electric materials (Su et al., 2004; Ahn et al., 2003; Lorenzetti et al., 2005; Chen et al., 2005). Recently, 1,8-disubstituted naphthalenes have received much attention as unique structured aromatic core compounds, exemplified by dendron cores, supramolecular building blocks, and so on (Wang & Guen, 1995; Allen et al., 1998; Crasto & Stevens, 1998, 2002). In this paper, the crystallographical structural characteristics of a 1,8-diaroylated naphthalene derivative having two methoxy groups at the 2,7-positions are described.

The molecular structure of the title molecule is displayed in Fig. 1. The two 4-chlorobenzoyl groups are situated in anti orientation and approximately parallel. Furthermore, these 4-chlorobenzoyl groups are twisted away from the attached naphthalene ring. The interplanar angle between the best planes of two benzene rings is 7.99 (8)°. On the other hand, the two interplanar angles between the best planes of the peri-chlorophenyl rings and the naphthalene ring are 71.55 (7) and 71.98 (7)°.

The torsion angles between the carbonyl groups and the naphthalene ring are relatively large [C10—C1—C11—O1 = 64.9 (2)° and C10—C9—C18—O2 64.4 (2)°] and those between 4-chlorophenyl groups and carbonyl groups are rather small [O1—C11—C12—C17 = 0.0 (2)° and O2—C18—C19—C20 = -3.8 (3)°].

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Ahn et al. (2003); Allen et al. (1998); Burnett & Johnson (1996); Chen et al. (2005); Crasto & Stevens (1998, 2002); Lorenzetti et al. (2005); Su et al. (2004); Wang & Guen (1995).

Experimental top

The title compound was prepared by electrophilic aromatic diaroylation reaction of 2,7-dimethoxynaphthalene with 4-chlorobenzoic acid. Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol and ethyl acetate.

Structure description top

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1).

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: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I), with the atom-labeling scheme and displacement ellipsoids drawn at 50% probability level.

1,8-Bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene top

Crystal data top

C₂₆H₁₈Cl₂O₄	D_x = 1.459 Mg m⁻³
M_r = 465.30	Melting point = 489–490 K
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2c -2n	Cell parameters from 31902 reflections
a = 20.3750 (12) Å	θ = 3.3–68.2°
b = 13.3513 (8) Å	µ = 3.03 mm⁻¹
c = 7.7876 (5) Å	T = 223 K
V = 2118.5 (2) Å³	Platelet, colorless
Z = 4	0.40 × 0.20 × 0.10 mm
F(000) = 960

Data collection top

Rigaku R-AXIS RAPID diffractometer	3800 independent reflections
Radiation source: rotating anode	3554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.0°
ω scans	h = −24→24
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −16→16
T_min = 0.469, T_max = 0.739	l = −9→9
32358 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0468P)² + 0.0953P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3800 reflections	Δρ_max = 0.12 e Å⁻³
291 parameters	Δρ_min = −0.20 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1700 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (10)

Crystal data top

C₂₆H₁₈Cl₂O₄	V = 2118.5 (2) Å³
M_r = 465.30	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 20.3750 (12) Å	µ = 3.03 mm⁻¹
b = 13.3513 (8) Å	T = 223 K
c = 7.7876 (5) Å	0.40 × 0.20 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3800 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3554 reflections with I > 2σ(I)
T_min = 0.469, T_max = 0.739	R_int = 0.039
32358 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.075	Δρ_max = 0.12 e Å⁻³
S = 1.08	Δρ_min = −0.20 e Å⁻³
3800 reflections	Absolute structure: Flack (1983), 1700 Friedel pairs
291 parameters	Absolute structure parameter: 0.006 (10)
3 restraints

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	0.32552 (2)	0.90210 (4)	1.19556 (7)	0.05618 (15)
Cl2	0.29868 (3)	0.63123 (4)	0.00821 (7)	0.05820 (15)
O1	0.14460 (6)	0.88124 (9)	0.48055 (16)	0.0385 (3)
O2	0.13748 (6)	0.67260 (10)	0.75073 (16)	0.0441 (3)
O3	0.06248 (6)	1.04973 (10)	0.73866 (19)	0.0556 (4)
O4	0.03508 (6)	0.53236 (10)	0.4943 (2)	0.0584 (4)
C1	0.05413 (8)	0.88005 (13)	0.6674 (2)	0.0378 (4)
C2	0.02311 (9)	0.96871 (15)	0.7127 (2)	0.0453 (4)
C3	−0.04597 (10)	0.97323 (18)	0.7289 (3)	0.0558 (5)
H3	−0.0665	1.0325	0.7659	0.067*
C4	−0.08219 (9)	0.89153 (18)	0.6905 (3)	0.0584 (6)
H4	−0.1281	0.8956	0.6987	0.070*
C5	−0.05357 (9)	0.80051 (17)	0.6387 (3)	0.0486 (5)
C6	−0.09200 (10)	0.7168 (2)	0.5924 (3)	0.0604 (6)
H6	−0.1380	0.7223	0.5973	0.073*
C7	−0.06547 (10)	0.62956 (19)	0.5416 (3)	0.0589 (6)
H7	−0.0927	0.5758	0.5096	0.071*
C8	0.00361 (10)	0.61901 (15)	0.5364 (3)	0.0466 (5)
C9	0.04402 (8)	0.69843 (14)	0.5811 (2)	0.0385 (4)
C10	0.01669 (8)	0.79240 (15)	0.6304 (2)	0.0390 (4)
C11	0.12709 (8)	0.88543 (12)	0.6302 (2)	0.0338 (4)
C12	0.17524 (8)	0.89343 (12)	0.7723 (2)	0.0320 (4)
C13	0.15574 (9)	0.89425 (13)	0.9437 (2)	0.0382 (4)
H13	0.1108	0.8925	0.9708	0.046*
C14	0.20150 (9)	0.89768 (14)	1.0747 (3)	0.0399 (4)
H14	0.1882	0.8985	1.1903	0.048*
C15	0.26734 (9)	0.89991 (12)	1.0318 (2)	0.0374 (4)
C16	0.28802 (8)	0.89981 (14)	0.8630 (3)	0.0399 (4)
H16	0.3330	0.9022	0.8368	0.048*
C17	0.24226 (8)	0.89622 (12)	0.7340 (2)	0.0357 (4)
H17	0.2561	0.8956	0.6188	0.043*
C18	0.11656 (8)	0.67558 (13)	0.6044 (2)	0.0342 (4)
C19	0.16038 (8)	0.66156 (12)	0.4552 (2)	0.0337 (4)
C20	0.22786 (8)	0.65045 (12)	0.4826 (2)	0.0364 (4)
H20	0.2443	0.6490	0.5953	0.044*
C21	0.27030 (9)	0.64168 (13)	0.3462 (2)	0.0401 (4)
H21	0.3157	0.6350	0.3650	0.048*
C22	0.24542 (9)	0.64286 (12)	0.1807 (3)	0.0398 (4)
C23	0.17872 (10)	0.65289 (15)	0.1491 (2)	0.0443 (5)
H23	0.1625	0.6528	0.0361	0.053*
C24	0.13658 (9)	0.66302 (13)	0.2872 (2)	0.0389 (4)
H24	0.0914	0.6710	0.2677	0.047*
C25	0.03606 (12)	1.14600 (16)	0.6982 (3)	0.0600 (6)
H25A	0.0703	1.1961	0.7074	0.072*
H25B	0.0010	1.1619	0.7779	0.072*
H25C	0.0189	1.1454	0.5820	0.072*
C26	−0.00149 (13)	0.44196 (19)	0.4806 (4)	0.0782 (8)
H26A	0.0282	0.3865	0.4595	0.094*
H26B	−0.0324	0.4474	0.3862	0.094*
H26C	−0.0253	0.4303	0.5866	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0528 (3)	0.0702 (3)	0.0456 (3)	−0.0039 (2)	−0.0186 (2)	0.0032 (3)
Cl2	0.0695 (3)	0.0640 (3)	0.0411 (3)	0.0090 (2)	0.0195 (3)	0.0026 (3)
O1	0.0395 (6)	0.0506 (6)	0.0256 (7)	0.0026 (5)	0.0037 (5)	0.0014 (5)
O2	0.0432 (7)	0.0629 (8)	0.0260 (7)	0.0035 (6)	−0.0068 (5)	0.0030 (6)
O3	0.0524 (8)	0.0560 (8)	0.0583 (10)	0.0180 (6)	−0.0112 (7)	−0.0095 (7)
O4	0.0549 (8)	0.0568 (8)	0.0636 (10)	−0.0224 (6)	−0.0059 (8)	0.0039 (8)
C1	0.0316 (8)	0.0564 (11)	0.0253 (10)	0.0059 (7)	0.0008 (7)	0.0034 (7)
C2	0.0426 (9)	0.0664 (11)	0.0270 (10)	0.0166 (8)	−0.0010 (8)	0.0001 (9)
C3	0.0446 (10)	0.0867 (15)	0.0360 (12)	0.0263 (10)	0.0044 (8)	0.0029 (11)
C4	0.0332 (9)	0.1042 (17)	0.0378 (12)	0.0172 (10)	0.0088 (9)	0.0211 (11)
C5	0.0307 (9)	0.0822 (15)	0.0330 (11)	0.0017 (9)	0.0014 (7)	0.0184 (9)
C6	0.0313 (9)	0.0977 (18)	0.0523 (13)	−0.0086 (10)	−0.0022 (8)	0.0281 (13)
C7	0.0421 (11)	0.0840 (15)	0.0505 (15)	−0.0237 (11)	−0.0108 (10)	0.0214 (11)
C8	0.0436 (10)	0.0599 (11)	0.0361 (11)	−0.0137 (8)	−0.0064 (8)	0.0097 (8)
C9	0.0333 (8)	0.0566 (11)	0.0256 (9)	−0.0070 (7)	−0.0017 (7)	0.0093 (8)
C10	0.0294 (8)	0.0633 (12)	0.0243 (9)	0.0014 (7)	0.0003 (7)	0.0105 (8)
C11	0.0345 (8)	0.0383 (9)	0.0286 (10)	0.0053 (7)	0.0016 (7)	0.0012 (7)
C12	0.0315 (8)	0.0365 (8)	0.0280 (9)	0.0034 (6)	0.0007 (7)	0.0006 (7)
C13	0.0343 (9)	0.0507 (10)	0.0298 (10)	0.0009 (7)	0.0036 (7)	0.0012 (7)
C14	0.0451 (10)	0.0483 (11)	0.0264 (10)	0.0009 (7)	0.0020 (8)	0.0011 (7)
C15	0.0402 (9)	0.0378 (9)	0.0341 (11)	0.0017 (6)	−0.0076 (8)	0.0013 (7)
C16	0.0317 (8)	0.0456 (10)	0.0423 (12)	0.0035 (7)	−0.0003 (8)	−0.0002 (8)
C17	0.0356 (8)	0.0412 (9)	0.0302 (11)	0.0021 (7)	0.0032 (7)	−0.0013 (7)
C18	0.0361 (9)	0.0386 (9)	0.0280 (9)	−0.0065 (7)	−0.0015 (7)	0.0025 (7)
C19	0.0378 (8)	0.0344 (8)	0.0287 (9)	−0.0026 (6)	−0.0035 (7)	0.0003 (7)
C20	0.0380 (8)	0.0418 (9)	0.0293 (10)	−0.0015 (6)	−0.0054 (8)	−0.0003 (8)
C21	0.0399 (9)	0.0425 (9)	0.0378 (11)	0.0017 (7)	0.0017 (8)	−0.0018 (8)
C22	0.0511 (10)	0.0364 (8)	0.0318 (10)	0.0019 (7)	0.0090 (8)	0.0010 (8)
C23	0.0586 (12)	0.0486 (11)	0.0256 (11)	−0.0006 (8)	−0.0022 (8)	0.0035 (8)
C24	0.0398 (9)	0.0481 (10)	0.0286 (10)	−0.0017 (7)	−0.0062 (7)	0.0028 (8)
C25	0.0707 (14)	0.0596 (11)	0.0498 (14)	0.0249 (10)	−0.0082 (12)	−0.0090 (11)
C26	0.0898 (17)	0.0750 (16)	0.0698 (19)	−0.0461 (14)	0.0188 (15)	−0.0207 (14)

Geometric parameters (Å, º) top

Cl1—C15	1.7412 (18)	C12—C17	1.398 (2)
Cl2—C22	1.734 (2)	C13—C14	1.383 (3)
O1—C11	1.220 (2)	C13—H13	0.9400
O2—C18	1.217 (2)	C14—C15	1.383 (3)
O3—C2	1.362 (2)	C14—H14	0.9400
O3—C25	1.429 (2)	C15—C16	1.380 (3)
O4—C8	1.363 (3)	C16—C17	1.372 (3)
O4—C26	1.423 (2)	C16—H16	0.9400
C1—C2	1.388 (2)	C17—H17	0.9400
C1—C10	1.426 (3)	C18—C19	1.477 (2)
C1—C11	1.516 (2)	C19—C24	1.395 (2)
C2—C3	1.414 (3)	C19—C20	1.399 (2)
C3—C4	1.350 (3)	C20—C21	1.375 (2)
C3—H3	0.9400	C20—H20	0.9400
C4—C5	1.407 (3)	C21—C22	1.385 (3)
C4—H4	0.9400	C21—H21	0.9400
C5—C6	1.412 (3)	C22—C23	1.387 (3)
C5—C10	1.437 (2)	C23—C24	1.383 (3)
C6—C7	1.343 (3)	C23—H23	0.9400
C6—H6	0.9400	C24—H24	0.9400
C7—C8	1.415 (3)	C25—H25A	0.9700
C7—H7	0.9400	C25—H25B	0.9700
C8—C9	1.387 (2)	C25—H25C	0.9700
C9—C10	1.425 (3)	C26—H26A	0.9700
C9—C18	1.520 (2)	C26—H26B	0.9700
C11—C12	1.482 (2)	C26—H26C	0.9700
C12—C13	1.393 (3)

C2—O3—C25	117.40 (15)	C13—C14—H14	120.8
C8—O4—C26	119.47 (17)	C16—C15—C14	121.74 (17)
C2—C1—C10	120.50 (16)	C16—C15—Cl1	119.31 (14)
C2—C1—C11	117.05 (16)	C14—C15—Cl1	118.96 (15)
C10—C1—C11	121.65 (15)	C17—C16—C15	119.36 (16)
O3—C2—C1	116.56 (15)	C17—C16—H16	120.3
O3—C2—C3	122.62 (18)	C15—C16—H16	120.3
C1—C2—C3	120.8 (2)	C16—C17—C12	120.55 (17)
C4—C3—C2	119.31 (19)	C16—C17—H17	119.7
C4—C3—H3	120.3	C12—C17—H17	119.7
C2—C3—H3	120.3	O2—C18—C19	121.37 (15)
C3—C4—C5	122.32 (18)	O2—C18—C9	117.32 (16)
C3—C4—H4	118.8	C19—C18—C9	121.27 (15)
C5—C4—H4	118.8	C24—C19—C20	119.07 (16)
C4—C5—C6	121.82 (18)	C24—C19—C18	121.70 (16)
C4—C5—C10	119.40 (19)	C20—C19—C18	119.17 (15)
C6—C5—C10	118.8 (2)	C21—C20—C19	120.62 (17)
C7—C6—C5	122.58 (18)	C21—C20—H20	119.7
C7—C6—H6	118.7	C19—C20—H20	119.7
C5—C6—H6	118.7	C20—C21—C22	119.20 (17)
C6—C7—C8	119.7 (2)	C20—C21—H21	120.4
C6—C7—H7	120.2	C22—C21—H21	120.4
C8—C7—H7	120.2	C21—C22—C23	121.61 (18)
O4—C8—C9	115.48 (16)	C21—C22—Cl2	119.40 (15)
O4—C8—C7	124.01 (18)	C23—C22—Cl2	118.99 (16)
C9—C8—C7	120.5 (2)	C24—C23—C22	118.69 (17)
C8—C9—C10	120.58 (17)	C24—C23—H23	120.7
C8—C9—C18	116.99 (17)	C22—C23—H23	120.7
C10—C9—C18	121.61 (15)	C23—C24—C19	120.79 (17)
C9—C10—C1	124.59 (15)	C23—C24—H24	119.6
C9—C10—C5	117.88 (17)	C19—C24—H24	119.6
C1—C10—C5	117.51 (17)	O3—C25—H25A	109.5
O1—C11—C12	121.52 (15)	O3—C25—H25B	109.5
O1—C11—C1	117.82 (15)	H25A—C25—H25B	109.5
C12—C11—C1	120.65 (15)	O3—C25—H25C	109.5
C13—C12—C17	118.88 (17)	H25A—C25—H25C	109.5
C13—C12—C11	121.81 (15)	H25B—C25—H25C	109.5
C17—C12—C11	119.27 (16)	O4—C26—H26A	109.5
C14—C13—C12	121.00 (17)	O4—C26—H26B	109.5
C14—C13—H13	119.5	H26A—C26—H26B	109.5
C12—C13—H13	119.5	O4—C26—H26C	109.5
C15—C14—C13	118.47 (18)	H26A—C26—H26C	109.5
C15—C14—H14	120.8	H26B—C26—H26C	109.5

C25—O3—C2—C1	148.54 (19)	C10—C1—C11—O1	64.9 (2)
C25—O3—C2—C3	−30.9 (3)	C2—C1—C11—C12	76.3 (2)
C10—C1—C2—O3	−177.28 (16)	C10—C1—C11—C12	−113.86 (19)
C11—C1—C2—O3	−7.3 (3)	O1—C11—C12—C13	−177.41 (16)
C10—C1—C2—C3	2.2 (3)	C1—C11—C12—C13	1.3 (2)
C11—C1—C2—C3	172.14 (17)	O1—C11—C12—C17	0.0 (2)
O3—C2—C3—C4	175.8 (2)	C1—C11—C12—C17	178.72 (15)
C1—C2—C3—C4	−3.6 (3)	C17—C12—C13—C14	−0.1 (2)
C2—C3—C4—C5	1.6 (3)	C11—C12—C13—C14	177.36 (16)
C3—C4—C5—C6	−177.4 (2)	C12—C13—C14—C15	−0.2 (3)
C3—C4—C5—C10	1.8 (3)	C13—C14—C15—C16	0.7 (3)
C4—C5—C6—C7	179.5 (2)	C13—C14—C15—Cl1	−178.93 (14)
C10—C5—C6—C7	0.3 (3)	C14—C15—C16—C17	−0.8 (3)
C5—C6—C7—C8	1.2 (3)	Cl1—C15—C16—C17	178.81 (13)
C26—O4—C8—C9	167.4 (2)	C15—C16—C17—C12	0.5 (2)
C26—O4—C8—C7	−10.5 (3)	C13—C12—C17—C16	−0.1 (2)
C6—C7—C8—O4	176.9 (2)	C11—C12—C17—C16	−177.54 (15)
C6—C7—C8—C9	−0.9 (3)	C8—C9—C18—O2	−105.3 (2)
O4—C8—C9—C10	−178.93 (17)	C10—C9—C18—O2	64.4 (2)
C7—C8—C9—C10	−0.9 (3)	C8—C9—C18—C19	77.0 (2)
O4—C8—C9—C18	−9.1 (3)	C10—C9—C18—C19	−113.28 (19)
C7—C8—C9—C18	168.87 (18)	O2—C18—C19—C24	178.79 (17)
C8—C9—C10—C1	−175.68 (19)	C9—C18—C19—C24	−3.7 (2)
C18—C9—C10—C1	15.0 (3)	O2—C18—C19—C20	−3.8 (3)
C8—C9—C10—C5	2.4 (3)	C9—C18—C19—C20	173.77 (15)
C18—C9—C10—C5	−166.91 (16)	C24—C19—C20—C21	0.4 (2)
C2—C1—C10—C9	179.28 (17)	C18—C19—C20—C21	−177.12 (16)
C11—C1—C10—C9	9.8 (3)	C19—C20—C21—C22	−0.7 (3)
C2—C1—C10—C5	1.2 (3)	C20—C21—C22—C23	0.1 (3)
C11—C1—C10—C5	−168.31 (16)	C20—C21—C22—Cl2	−179.69 (13)
C4—C5—C10—C9	178.65 (17)	C21—C22—C23—C24	0.7 (3)
C6—C5—C10—C9	−2.1 (3)	Cl2—C22—C23—C24	−179.44 (15)
C4—C5—C10—C1	−3.1 (3)	C22—C23—C24—C19	−1.0 (3)
C6—C5—C10—C1	176.11 (17)	C20—C19—C24—C23	0.5 (3)
C2—C1—C11—O1	−104.9 (2)	C18—C19—C24—C23	177.95 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.94	2.58	3.414 (3)	148
C14—H14···O1ⁱⁱ	0.94	2.44	3.374 (3)	172
C23—H23···O2ⁱⁱⁱ	0.94	2.30	3.225 (3)	170

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈Cl₂O₄
M_r	465.30
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	223
a, b, c (Å)	20.3750 (12), 13.3513 (8), 7.7876 (5)
V (Å³)	2118.5 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.03
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.469, 0.739
No. of measured, independent and observed [I > 2σ(I)] reflections	32358, 3800, 3554
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.08
No. of reflections	3800
No. of parameters	291
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.20
Absolute structure	Flack (1983), 1700 Friedel pairs
Absolute structure parameter	0.006 (10)

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).