Benzoximate

Kim, T.H.; Moon, S.-H.; Kim, J.; Park, K.-M.

doi:10.1107/S1600536812044248

Benzoximate

T. H. Kim, S.-H. Moon, J. Kim and K.-M. Park

In the title compound [systematic name: (3-chloro-2,6-dimethoxyphenyl)(ethoxyimino)methyl benzoate], C₁₈H₁₈ClNO₅, the phenyl and chlorodimethoxyphenyl rings are linked by the ethoxyiminomethyl benzoate system such that they are almost perpendicular to each other with the dihedral angle between them being 85.72 (9)°. In the crystal, C—H

O and C—H

Cl hydrogen bonds between the phenyl and chlorodimethoxyphenyl rings generate R₂²(8) rings which link the molecules into zigzag chains along the b axis. Additional C—H

O contacts, together with weak intermolecular C—H

π interactions, further link the molecules into a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812044248/sj5275sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812044248/sj5275Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812044248/sj5275Isup3.cml Supplementary material

CCDC reference: 909895

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.005 Å
R factor = 0.073
wR factor = 0.138
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        3.2 Ratio
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0048 Ang
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  O1      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18    ..  CL1     ..       2.89 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     27.268
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.514
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.147
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in CIF ...          ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          !

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

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

Comment top

Benzoximate (IUPAC name: (3-chloro-2,6-dimethoxyphenyl)(ethoxyimino)methyl benzoate) is an acaricide widely used in agriculture targeting ticks and mites (Kim et al., 2007). However, until now its crystal structure has not been reported.

In the title compound (Fig. 1), the two aromatic rings are almost perpendicular to each other with the dihedral angle between them being 85.72 (9)°. Of the two methoxy methyl groups, one (C7) is almost perpendicular to the benzene ring plane [torsion angle C1–C6–O1–C7 = 84.0 (4) °] whereas the other (C8) is nearly parallel to it [torsion angle C3–C4–O2–C8 = 3.8 (5) °]. All the bond distances and bond angles within the molecule agree with values reported in the Cambridge Structural Database (Allen, 2002).

In the crystal, C17—H17···O1 and C18—H18···Cl1 hydrogen bonds generate R²₂(8) rings (Bernstein et al., 1995). Additional C3—H3···O5 hydrogen bonds and C–H···π contacts, Table 1, further link the molecules into a three dimensional network.

Related literature top

For information on the toxicity of the title compound, see: Kim et al. (2007). For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. X-ray quality single crystals were obtained by slow evaporation of a solution of the title compound in dichloromethane at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.

Fig. 2. Crystal packing of the title compound with intermolecular C–H···O and C–H···Cl hydrogen bonds and C–H···π interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively. (Symmetry codes: (i) x, -y + 1/2, z - 1/2; (ii) -x + 1, y - 1/2, -z + 1/2; (iii) -x, -y + 1, -z; (iv) -x, y + 1/2, -z + 1/2.)

(3-Chloro-2,6-dimethoxyphenyl)(ethoxyimino)methyl benzoate top

Crystal data top

C₁₈H₁₈ClNO₅	F(000) = 760
M_r = 363.78	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2737 reflections
a = 9.4262 (10) Å	θ = 2.2–25.6°
b = 12.9863 (14) Å	µ = 0.23 mm⁻¹
c = 15.4227 (16) Å	T = 223 K
β = 102.843 (2)°	Block, colourless
V = 1840.7 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.933, T_max = 0.977	k = −8→16
9736 measured reflections	l = −18→19

Refinement top

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0351P)² + 1.3636P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₈ClNO₅	V = 1840.7 (3) Å³
M_r = 363.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4262 (10) Å	µ = 0.23 mm⁻¹
b = 12.9863 (14) Å	T = 223 K
c = 15.4227 (16) Å	0.30 × 0.20 × 0.10 mm
β = 102.843 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3606 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2298 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.977	R_int = 0.049
9736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.10	Δρ_max = 0.22 e Å⁻³
3606 reflections	Δρ_min = −0.30 e Å⁻³
229 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	0.31473 (12)	0.56710 (7)	0.07179 (7)	0.0649 (3)
O1	0.1499 (2)	0.42350 (16)	0.16181 (13)	0.0405 (6)
O2	0.1097 (3)	0.15458 (19)	−0.04964 (16)	0.0583 (7)
O3	−0.1289 (3)	0.17796 (19)	0.17061 (16)	0.0578 (7)
O4	0.0986 (2)	0.12350 (16)	0.12436 (14)	0.0404 (6)
O5	0.2986 (3)	0.18389 (17)	0.21829 (15)	0.0484 (6)
N1	−0.0722 (3)	0.2521 (2)	0.12132 (17)	0.0415 (7)
C1	0.2563 (4)	0.4441 (3)	0.0356 (2)	0.0431 (9)
C2	0.2902 (4)	0.4053 (3)	−0.0402 (2)	0.0488 (9)
H2	0.3459	0.4449	−0.0714	0.059*
C3	0.2430 (4)	0.3084 (3)	−0.0708 (2)	0.0477 (9)
H3	0.2657	0.2823	−0.1229	0.057*
C4	0.1622 (3)	0.2502 (3)	−0.0243 (2)	0.0396 (8)
C5	0.1277 (3)	0.2883 (2)	0.0537 (2)	0.0328 (7)
C6	0.1751 (3)	0.3869 (2)	0.0833 (2)	0.0355 (8)
C7	0.0273 (4)	0.4934 (3)	0.1513 (2)	0.0539 (10)
H7A	0.0326	0.5436	0.1055	0.081*
H7B	0.0300	0.5287	0.2070	0.081*
H7C	−0.0627	0.4548	0.1342	0.081*
C8	0.1477 (6)	0.1095 (4)	−0.1262 (3)	0.0996 (19)
H8A	0.1149	0.1539	−0.1773	0.149*
H8B	0.1014	0.0427	−0.1378	0.149*
H8C	0.2525	0.1014	−0.1153	0.149*
C9	0.0461 (3)	0.2231 (2)	0.10433 (19)	0.0331 (7)
C10	−0.2591 (5)	0.2193 (3)	0.1924 (3)	0.0682 (12)
H10A	−0.2394	0.2897	0.2147	0.082*
H10B	−0.2832	0.1780	0.2404	0.082*
C11	−0.3862 (5)	0.2206 (4)	0.1162 (3)	0.0910 (16)
H11A	−0.3699	0.2706	0.0727	0.137*
H11B	−0.4727	0.2393	0.1368	0.137*
H11C	−0.3991	0.1529	0.0891	0.137*
C12	0.2377 (3)	0.1144 (2)	0.17402 (19)	0.0328 (7)
C13	0.2986 (3)	0.0111 (2)	0.16451 (19)	0.0311 (7)
C14	0.2277 (3)	−0.0602 (2)	0.1025 (2)	0.0390 (8)
H14	0.1367	−0.0443	0.0658	0.047*
C15	0.2915 (4)	−0.1537 (3)	0.0952 (2)	0.0466 (9)
H15	0.2432	−0.2023	0.0539	0.056*
C16	0.4257 (4)	−0.1772 (3)	0.1479 (2)	0.0479 (9)
H16	0.4684	−0.2415	0.1422	0.058*
C17	0.4976 (4)	−0.1070 (3)	0.2091 (2)	0.0487 (9)
H17	0.5895	−0.1230	0.2447	0.058*
C18	0.4341 (4)	−0.0130 (3)	0.2177 (2)	0.0412 (8)
H18	0.4824	0.0350	0.2597	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0716 (7)	0.0457 (5)	0.0686 (7)	−0.0158 (5)	−0.0033 (5)	0.0124 (5)
O1	0.0476 (14)	0.0375 (12)	0.0331 (12)	0.0087 (11)	0.0017 (10)	−0.0030 (10)
O2	0.0666 (19)	0.0633 (16)	0.0548 (16)	−0.0204 (14)	0.0342 (13)	−0.0286 (13)
O3	0.0556 (17)	0.0620 (16)	0.0683 (17)	0.0102 (13)	0.0405 (14)	0.0162 (14)
O4	0.0319 (13)	0.0349 (12)	0.0532 (14)	0.0003 (10)	0.0072 (11)	−0.0047 (11)
O5	0.0540 (16)	0.0413 (14)	0.0443 (14)	−0.0034 (12)	−0.0011 (12)	−0.0114 (12)
N1	0.0387 (17)	0.0502 (17)	0.0413 (16)	0.0052 (14)	0.0209 (13)	0.0051 (14)
C1	0.037 (2)	0.042 (2)	0.045 (2)	−0.0017 (16)	−0.0029 (17)	0.0071 (17)
C2	0.035 (2)	0.061 (2)	0.051 (2)	−0.0006 (18)	0.0107 (17)	0.017 (2)
C3	0.041 (2)	0.063 (2)	0.044 (2)	0.0027 (19)	0.0217 (17)	0.0002 (19)
C4	0.0301 (18)	0.049 (2)	0.0417 (19)	−0.0001 (16)	0.0116 (15)	−0.0066 (17)
C5	0.0265 (18)	0.0394 (18)	0.0324 (17)	0.0022 (14)	0.0061 (13)	−0.0020 (15)
C6	0.0343 (19)	0.0370 (18)	0.0309 (17)	0.0077 (15)	−0.0020 (14)	0.0005 (15)
C7	0.064 (3)	0.046 (2)	0.051 (2)	0.0208 (19)	0.0107 (19)	−0.0014 (18)
C8	0.130 (5)	0.099 (4)	0.093 (4)	−0.037 (3)	0.075 (3)	−0.063 (3)
C9	0.0339 (19)	0.0333 (17)	0.0318 (17)	0.0007 (15)	0.0065 (15)	−0.0051 (14)
C10	0.063 (3)	0.079 (3)	0.077 (3)	0.010 (2)	0.047 (2)	0.011 (2)
C11	0.054 (3)	0.140 (5)	0.088 (3)	0.007 (3)	0.036 (3)	0.001 (3)
C12	0.0356 (19)	0.0361 (18)	0.0292 (17)	−0.0038 (16)	0.0124 (15)	0.0001 (15)
C13	0.0314 (18)	0.0348 (17)	0.0282 (16)	−0.0014 (14)	0.0089 (14)	−0.0022 (14)
C14	0.0313 (19)	0.0422 (19)	0.0415 (18)	0.0051 (16)	0.0040 (15)	−0.0053 (16)
C15	0.041 (2)	0.044 (2)	0.053 (2)	0.0018 (17)	0.0070 (18)	−0.0115 (17)
C16	0.041 (2)	0.044 (2)	0.063 (2)	0.0039 (17)	0.0187 (19)	−0.0032 (18)
C17	0.0304 (19)	0.052 (2)	0.061 (2)	0.0066 (17)	0.0061 (17)	0.0089 (19)
C18	0.034 (2)	0.047 (2)	0.0396 (19)	−0.0028 (16)	0.0003 (15)	0.0001 (16)

Geometric parameters (Å, º) top

Cl1—C1	1.740 (3)	C7—H7C	0.9700
O1—C6	1.370 (4)	C8—H8A	0.9700
O1—C7	1.450 (4)	C8—H8B	0.9700
O2—C4	1.361 (4)	C8—H8C	0.9700
O2—C8	1.433 (4)	C10—C11	1.481 (6)
O3—N1	1.404 (3)	C10—H10A	0.9800
O3—C10	1.446 (4)	C10—H10B	0.9800
O4—C12	1.368 (4)	C11—H11A	0.9700
O4—C9	1.395 (4)	C11—H11B	0.9700
O5—C12	1.198 (3)	C11—H11C	0.9700
N1—C9	1.259 (4)	C12—C13	1.479 (4)
C1—C2	1.374 (5)	C13—C14	1.391 (4)
C1—C6	1.389 (5)	C13—C18	1.392 (4)
C2—C3	1.382 (5)	C14—C15	1.371 (4)
C2—H2	0.9400	C14—H14	0.9400
C3—C4	1.382 (5)	C15—C16	1.377 (5)
C3—H3	0.9400	C15—H15	0.9400
C4—C5	1.404 (4)	C16—C17	1.377 (5)
C5—C6	1.398 (4)	C16—H16	0.9400
C5—C9	1.478 (4)	C17—C18	1.379 (5)
C7—H7A	0.9700	C17—H17	0.9400
C7—H7B	0.9700	C18—H18	0.9400

C6—O1—C7	114.1 (2)	N1—C9—C5	121.8 (3)
C4—O2—C8	117.9 (3)	O4—C9—C5	116.6 (3)
N1—O3—C10	108.5 (3)	O3—C10—C11	113.4 (3)
C12—O4—C9	116.9 (2)	O3—C10—H10A	108.9
C9—N1—O3	111.7 (3)	C11—C10—H10A	108.9
C2—C1—C6	120.9 (3)	O3—C10—H10B	108.9
C2—C1—Cl1	119.5 (3)	C11—C10—H10B	108.9
C6—C1—Cl1	119.6 (3)	H10A—C10—H10B	107.7
C1—C2—C3	120.5 (3)	C10—C11—H11A	109.5
C1—C2—H2	119.8	C10—C11—H11B	109.5
C3—C2—H2	119.8	H11A—C11—H11B	109.5
C2—C3—C4	119.6 (3)	C10—C11—H11C	109.5
C2—C3—H3	120.2	H11A—C11—H11C	109.5
C4—C3—H3	120.2	H11B—C11—H11C	109.5
O2—C4—C3	123.9 (3)	O5—C12—O4	122.2 (3)
O2—C4—C5	115.4 (3)	O5—C12—C13	126.3 (3)
C3—C4—C5	120.7 (3)	O4—C12—C13	111.5 (3)
C6—C5—C4	119.0 (3)	C14—C13—C18	119.6 (3)
C6—C5—C9	121.2 (3)	C14—C13—C12	122.3 (3)
C4—C5—C9	119.8 (3)	C18—C13—C12	118.1 (3)
O1—C6—C1	120.4 (3)	C15—C14—C13	119.6 (3)
O1—C6—C5	120.0 (3)	C15—C14—H14	120.2
C1—C6—C5	119.4 (3)	C13—C14—H14	120.2
O1—C7—H7A	109.5	C14—C15—C16	120.6 (3)
O1—C7—H7B	109.5	C14—C15—H15	119.7
H7A—C7—H7B	109.5	C16—C15—H15	119.7
O1—C7—H7C	109.5	C15—C16—C17	120.4 (3)
H7A—C7—H7C	109.5	C15—C16—H16	119.8
H7B—C7—H7C	109.5	C17—C16—H16	119.8
O2—C8—H8A	109.5	C16—C17—C18	119.6 (3)
O2—C8—H8B	109.5	C16—C17—H17	120.2
H8A—C8—H8B	109.5	C18—C17—H17	120.2
O2—C8—H8C	109.5	C17—C18—C13	120.2 (3)
H8A—C8—H8C	109.5	C17—C18—H18	119.9
H8B—C8—H8C	109.5	C13—C18—H18	119.9
N1—C9—O4	121.2 (3)

C10—O3—N1—C9	176.3 (3)	O3—N1—C9—C5	−179.5 (3)
C6—C1—C2—C3	0.5 (5)	C12—O4—C9—N1	−126.9 (3)
Cl1—C1—C2—C3	−179.0 (3)	C12—O4—C9—C5	59.6 (3)
C1—C2—C3—C4	−0.5 (5)	C6—C5—C9—N1	58.3 (4)
C8—O2—C4—C3	3.8 (5)	C4—C5—C9—N1	−123.5 (3)
C8—O2—C4—C5	−176.9 (4)	C6—C5—C9—O4	−128.2 (3)
C2—C3—C4—O2	179.3 (3)	C4—C5—C9—O4	50.0 (4)
C2—C3—C4—C5	0.0 (5)	N1—O3—C10—C11	74.9 (4)
O2—C4—C5—C6	−178.7 (3)	C9—O4—C12—O5	19.6 (4)
C3—C4—C5—C6	0.6 (5)	C9—O4—C12—C13	−160.0 (2)
O2—C4—C5—C9	3.0 (4)	O5—C12—C13—C14	−171.1 (3)
C3—C4—C5—C9	−177.6 (3)	O4—C12—C13—C14	8.4 (4)
C7—O1—C6—C1	84.0 (4)	O5—C12—C13—C18	6.6 (5)
C7—O1—C6—C5	−100.4 (3)	O4—C12—C13—C18	−173.9 (3)
C2—C1—C6—O1	175.7 (3)	C18—C13—C14—C15	0.7 (5)
Cl1—C1—C6—O1	−4.7 (4)	C12—C13—C14—C15	178.3 (3)
C2—C1—C6—C5	0.1 (5)	C13—C14—C15—C16	−0.8 (5)
Cl1—C1—C6—C5	179.7 (2)	C14—C15—C16—C17	0.2 (5)
C4—C5—C6—O1	−176.3 (3)	C15—C16—C17—C18	0.4 (5)
C9—C5—C6—O1	1.9 (4)	C16—C17—C18—C13	−0.5 (5)
C4—C5—C6—C1	−0.7 (4)	C14—C13—C18—C17	0.0 (5)
C9—C5—C6—C1	177.5 (3)	C12—C13—C18—C17	−177.7 (3)
O3—N1—C9—O4	7.3 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5ⁱ	0.94	2.57	3.409 (4)	148
C17—H17···O1ⁱⁱ	0.94	2.63	3.496 (4)	154
C18—H18···Cl1ⁱⁱ	0.94	2.89	3.716 (3)	147
C7—H7A···Cg1ⁱⁱⁱ	0.97	2.90	3.570 (4)	127
C10—H10A···Cg2^iv	0.98	3.01	3.740 (5)	132

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈ClNO₅
M_r	363.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	9.4262 (10), 12.9863 (14), 15.4227 (16)
β (°)	102.843 (2)
V (Å³)	1840.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.933, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	9736, 3606, 2298
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.138, 1.10
No. of reflections	3606
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.30

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5ⁱ	0.94	2.57	3.409 (4)	148.3
C17—H17···O1ⁱⁱ	0.94	2.63	3.496 (4)	153.8
C18—H18···Cl1ⁱⁱ	0.94	2.89	3.716 (3)	146.8
C7—H7A···Cg1ⁱⁱⁱ	0.97	2.90	3.570 (4)	126.8
C10—H10A···Cg2^iv	0.98	3.01	3.740 (5)	132.3

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

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