3-(2-Chloro­phen­yl)-1,5-bis­(4-chloro­phen­yl)pentane-1,5-dione

Jasinski, J.P.; Butcher, R.J.; Yathirajan, H.S.; Narayana, B.; Swamy, M.T.

doi:10.1107/S1600536807059089

3-(2-Chlorophenyl)-1,5-bis(4-chlorophenyl)pentane-1,5-dione

J. P. Jasinski, R. J. Butcher, H. S. Yathirajan, B. Narayana and M. T. Swamy

O interactions between an H atom from each of the two 4-chlorophenyl groups and a ketone O atom in neighboring molecules, which link the molecules into chains diagonally along the ac plane of the unit cell. Additional intermolecular π–π stacking interactions occur between adjacent 2-chlorophenyl rings as well as between one of the 4-chlorophenyl rings and a 2-chlorophenyl ring, the distances between the centroids of interacting rings being 3.931 (6) and 3.9915 (4) Å, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059089/at2485sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059089/at2485Isup2.hkl Contains datablock I

CCDC reference: 673015

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.041
wR factor = 0.118
Data-to-parameter ratio = 26.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.712     0.877
            Tmin(prime) and Tmax expected:      0.806     0.877
            RR(prime) =      0.884
            Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5A    -   C6A     ..       5.01 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6A
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         13

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

1,5-Diketones are important synthetic intermediates and starting materials in the synthesis of many heterocyclic compounds (Hirsch & Bailey, 1978; Krohnke, 1976). The structures of related compounds viz., 1,5-bis(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)pentane-1,5-dione (Insuasty et al. 2006), 1,5-(4-dichlorophenyl)-3-(2,5-dimethoxyphenyl)pentane-1,5-dione (Teh et al. 2006), 3-(2-furyl)-1,5-bis(4-methylphenyl)pentane-1,5-dione (Huang et al. 2006), 1,5-bis(4-chlorophenyl)-3-(4-pyridyl)pentane-1,5dione (Qiu et al. 2006a), 3-(3-chlorophenyl)-1,5-bis(4-nitrophenyl)pentane-1,5-dione (Qiu et al. 2006b), 1,5-bis (3-bromothien-2-yl) -3- (2,3,5-trichlorophenyl)pentane-1,5-dione, (Butcher et al. 2007), 1,5-bis(3-bromo-2-thienyl)-3-(3-nitrophenyl)pentane-1,5-dione (Yathirajan et al. 2006), 1,5-bis(4-bromophenyl)-3-(3-nitrophenyl)pentane-1,5-dione, (Yathirajan et al. 2007) have been reported. A new 1,5-dione, (I), C₂₃H₁₇Cl₃O₂ was synthesized and the crystal structure is reported here.

In the title compound, C₂₃H₁₇Cl₃O₂, the dihedral angles between the 2-chlorophenyl group and the two 4-chlorophenyl groups are 88.9 (3) and 12.9 (2)°, while the angle between the mean planes of the two 4-chlorophenyl groups is 77.9 (5)° (Fig. 1). The crystal packing is stabilized by intermolecular C–H···O interactions between a hydrogen atom from each of the two the two 4-chlorophenyl groups and its nearby ketone oxygen in neighboring molecules which link the molecules into chains diagonally and oblique along the ac plane of the unit cell (Fig. 2). Additional intermolecular π-π stacking interactions occur between adjacent 2-chlorophenyl rings [Cg3 = center of gravity of the 4-chlorolphenyl ring (C3B–C8B); Cg3···Cg3 = 3.931 (6) Å; 1 - x, 1 - y, -z] as well as between one of the 4-chlorophenyl rings and a 2-chlorophenyl ring [Cg1 = center of gravity of the 2-chlorolphenyl ring (C1–C6); Cg1···Cg3 = 3.931 (6) Å; x, -1 + y, z].

Related literature top

For related structures, see: Insuasty et al. (2006); Teh et al. (2006); Huang et al. (2006); Qiu et al. (2006a,b); Butcher et al. (2007); Yathirajan et al. (2006, 2007). For related literature, see: Krohnke et al. (1976): Hirsch & Bailey, (1978).

Experimental top

4-Chloroacetophenone (1.54 g, 0.1 mol) in ethanol (30 ml) was mixed with 2-chlorobenzaldehyde (0.7 g, 0.05 mol) and the mixture was treated with an aqueous solution of sodium hydroxide (5 ml, 30%) (Fig. 3). This mixture was stirred well and left for 12 h. The resulting crude solid mass was collected by filtration, washed, dried and recrystallized from toluene (yield 85%., m.p.: 401 K). The initially formed 1-(4-methoxyphenyl)-3-(2-chlorophenyl)prop-2-en-1-one, underwent Michael addition, resulting in the formation of the novel title compound (I). Analysis found: C 63.90, H 3.94%; C₂₃H₁₇Cl₃O₂ requires: C 63.98, H 3.97%.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed down the b axis. Dashed lines indicate intramolecular C—H···O hydrogen bonds.
	Fig. 3. Synthetic scheme for C₂₃H₁₇Cl₃O₂.

3-(2-Chlorophenyl)-1,5-bis(4-chlorophenyl)pentane-1,5-dione top

Crystal data top

C₂₃H₁₇Cl₃O₂	Z = 2
M_r = 431.72	F(000) = 444
Triclinic, P1	D_x = 1.417 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1717 (8) Å	Cell parameters from 4806 reflections
b = 7.7000 (15) Å	θ = 4.5–32.6°
c = 18.901 (6) Å	µ = 0.47 mm⁻¹
α = 85.88 (2)°	T = 296 K
β = 83.518 (15)°	Prism, pale yellow
γ = 77.656 (12)°	0.45 × 0.39 × 0.28 mm
V = 1011.9 (4) Å³

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	6690 independent reflections
Radiation source: fine-focus sealed tube	3147 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.7°, θ_min = 4.6°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→11
T_min = 0.712, T_max = 0.877	l = −28→25
14729 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0598P)²] where P = (F_o² + 2F_c²)/3
6690 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₃H₁₇Cl₃O₂	γ = 77.656 (12)°
M_r = 431.72	V = 1011.9 (4) Å³
Triclinic, P1	Z = 2
a = 7.1717 (8) Å	Mo Kα radiation
b = 7.7000 (15) Å	µ = 0.47 mm⁻¹
c = 18.901 (6) Å	T = 296 K
α = 85.88 (2)°	0.45 × 0.39 × 0.28 mm
β = 83.518 (15)°

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	6690 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3147 reflections with I > 2σ(I)
T_min = 0.712, T_max = 0.877	R_int = 0.024
14729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 0.93	Δρ_max = 0.24 e Å⁻³
6690 reflections	Δρ_min = −0.33 e Å⁻³
253 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
Cl	0.99371 (5)	0.01789 (6)	0.20354 (3)	0.07076 (15)
Cl1A	−0.20263 (8)	0.29570 (8)	0.60074 (3)	0.09081 (19)
Cl1B	0.84843 (6)	0.85651 (6)	0.01648 (3)	0.07311 (16)
O1A	0.59359 (15)	0.16616 (18)	0.37462 (6)	0.0739 (4)
O1B	0.22035 (13)	0.35855 (15)	0.14247 (6)	0.0630 (3)
C	0.55268 (17)	0.10895 (17)	0.23407 (7)	0.0392 (3)
H0A	0.6438	0.1859	0.2371	0.047*
C1	0.65483 (18)	−0.08305 (17)	0.24669 (7)	0.0407 (3)
C2	0.85377 (19)	−0.13735 (19)	0.23327 (7)	0.0464 (3)
C3	0.9461 (2)	−0.3130 (2)	0.24106 (9)	0.0629 (4)
H3A	1.0786	−0.3451	0.2314	0.075*
C4	0.8422 (3)	−0.4397 (2)	0.26302 (10)	0.0718 (5)
H4A	0.9041	−0.5583	0.2685	0.086*
C5	0.6468 (3)	−0.3926 (2)	0.27701 (10)	0.0725 (5)
H5A	0.5758	−0.4785	0.2925	0.087*
C6	0.5560 (2)	−0.2157 (2)	0.26790 (8)	0.0572 (4)
H6A	0.4231	−0.1855	0.2765	0.069*
C1A	0.37939 (18)	0.16621 (19)	0.28840 (7)	0.0445 (3)
H1AA	0.3097	0.2827	0.2731	0.053*
H1AB	0.2945	0.0835	0.2886	0.053*
C2A	0.4284 (2)	0.17464 (19)	0.36322 (7)	0.0455 (3)
C3A	0.26998 (19)	0.19997 (18)	0.42202 (7)	0.0438 (3)
C4A	0.3106 (2)	0.2179 (2)	0.49019 (8)	0.0632 (4)
H4AA	0.4371	0.2101	0.4990	0.076*
C5A	0.1676 (3)	0.2470 (3)	0.54553 (9)	0.0712 (5)
H5AA	0.1968	0.2592	0.5914	0.085*
C6A	−0.0180 (2)	0.2578 (2)	0.53224 (8)	0.0585 (4)
C7A	−0.0643 (2)	0.2376 (2)	0.46536 (9)	0.0646 (4)
H7AA	−0.1909	0.2435	0.4571	0.078*
C8A	0.0818 (2)	0.2081 (2)	0.41048 (8)	0.0549 (4)
H8AA	0.0525	0.1936	0.3649	0.066*
C1B	0.49133 (18)	0.12994 (18)	0.15762 (7)	0.0421 (3)
H1BA	0.6040	0.0926	0.1245	0.051*
H1BB	0.4045	0.0509	0.1539	0.051*
C2B	0.39471 (18)	0.31623 (18)	0.13577 (7)	0.0423 (3)
C3B	0.51050 (18)	0.44822 (18)	0.10689 (7)	0.0394 (3)
C4B	0.41837 (19)	0.61665 (19)	0.08326 (7)	0.0446 (3)
H4BA	0.2851	0.6452	0.0864	0.054*
C5B	0.5207 (2)	0.74129 (19)	0.05538 (8)	0.0499 (4)
H5BA	0.4577	0.8529	0.0391	0.060*
C6B	0.7180 (2)	0.69894 (19)	0.05180 (7)	0.0462 (3)
C7B	0.81408 (19)	0.5351 (2)	0.07542 (8)	0.0496 (4)
H7BA	0.9473	0.5092	0.0734	0.060*
C8B	0.71080 (19)	0.40966 (19)	0.10217 (8)	0.0473 (3)
H8BA	0.7751	0.2975	0.1174	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.03547 (19)	0.0776 (3)	0.0992 (4)	−0.01499 (18)	−0.0055 (2)	0.0040 (2)
Cl1A	0.0917 (4)	0.1141 (4)	0.0619 (3)	−0.0255 (3)	0.0284 (3)	−0.0169 (3)
Cl1B	0.0674 (3)	0.0560 (3)	0.0960 (4)	−0.0229 (2)	0.0084 (2)	0.0000 (2)
O1A	0.0434 (6)	0.1231 (11)	0.0596 (7)	−0.0194 (6)	−0.0097 (5)	−0.0207 (7)
O1B	0.0355 (5)	0.0703 (7)	0.0783 (8)	−0.0073 (5)	−0.0019 (5)	0.0118 (6)
C	0.0321 (6)	0.0422 (7)	0.0430 (7)	−0.0085 (5)	−0.0022 (5)	−0.0012 (6)
C1	0.0408 (7)	0.0434 (7)	0.0380 (7)	−0.0088 (6)	−0.0050 (6)	−0.0014 (6)
C2	0.0412 (7)	0.0518 (8)	0.0449 (8)	−0.0059 (6)	−0.0061 (6)	−0.0035 (6)
C3	0.0597 (9)	0.0604 (10)	0.0619 (10)	0.0079 (8)	−0.0141 (8)	−0.0075 (8)
C4	0.0958 (14)	0.0450 (9)	0.0655 (11)	0.0078 (9)	−0.0128 (10)	−0.0028 (8)
C5	0.0992 (14)	0.0477 (10)	0.0722 (12)	−0.0243 (9)	−0.0028 (10)	0.0048 (8)
C6	0.0560 (9)	0.0520 (9)	0.0626 (10)	−0.0152 (7)	0.0024 (8)	0.0025 (7)
C1A	0.0370 (6)	0.0525 (8)	0.0426 (8)	−0.0044 (6)	−0.0054 (6)	−0.0062 (6)
C2A	0.0436 (7)	0.0503 (8)	0.0434 (8)	−0.0097 (6)	−0.0063 (6)	−0.0047 (6)
C3A	0.0489 (8)	0.0460 (8)	0.0377 (8)	−0.0106 (6)	−0.0078 (6)	−0.0028 (6)
C4A	0.0553 (9)	0.0898 (12)	0.0461 (9)	−0.0146 (9)	−0.0080 (8)	−0.0116 (8)
C5A	0.0819 (12)	0.0957 (14)	0.0375 (9)	−0.0184 (10)	−0.0064 (9)	−0.0131 (8)
C6A	0.0639 (10)	0.0621 (10)	0.0472 (9)	−0.0140 (8)	0.0086 (8)	−0.0065 (7)
C7A	0.0496 (9)	0.0892 (13)	0.0559 (10)	−0.0167 (8)	−0.0001 (8)	−0.0095 (9)
C8A	0.0502 (8)	0.0758 (11)	0.0395 (8)	−0.0145 (7)	−0.0037 (7)	−0.0059 (7)
C1B	0.0411 (7)	0.0465 (8)	0.0381 (7)	−0.0089 (6)	0.0003 (6)	−0.0046 (6)
C2B	0.0365 (7)	0.0524 (8)	0.0360 (7)	−0.0047 (6)	−0.0034 (6)	−0.0022 (6)
C3B	0.0367 (6)	0.0482 (8)	0.0317 (7)	−0.0042 (6)	−0.0047 (5)	−0.0030 (6)
C4B	0.0388 (7)	0.0464 (8)	0.0463 (8)	−0.0010 (6)	−0.0074 (6)	−0.0056 (6)
C5B	0.0518 (8)	0.0411 (8)	0.0531 (9)	0.0001 (6)	−0.0081 (7)	−0.0029 (7)
C6B	0.0498 (8)	0.0462 (8)	0.0434 (8)	−0.0130 (6)	−0.0006 (6)	−0.0042 (6)
C7B	0.0361 (7)	0.0604 (9)	0.0500 (9)	−0.0069 (6)	−0.0039 (6)	0.0025 (7)
C8B	0.0377 (7)	0.0495 (8)	0.0496 (8)	−0.0004 (6)	−0.0049 (6)	0.0066 (6)

Geometric parameters (Å, º) top

Cl—C2	1.7439 (15)	C3A—C8A	1.379 (2)
Cl1A—C6A	1.7368 (16)	C4A—C5A	1.374 (2)
Cl1B—C6B	1.7380 (15)	C4A—H4AA	0.9300
O1A—C2A	1.2156 (16)	C5A—C6A	1.366 (2)
O1B—C2B	1.2173 (15)	C5A—H5AA	0.9300
C—C1	1.5183 (18)	C6A—C7A	1.370 (2)
C—C1A	1.5285 (18)	C7A—C8A	1.382 (2)
C—C1B	1.5450 (19)	C7A—H7AA	0.9300
C—H0A	0.9800	C8A—H8AA	0.9300
C1—C6	1.3759 (19)	C1B—C2B	1.5042 (19)
C1—C2	1.3976 (18)	C1B—H1BA	0.9700
C2—C3	1.379 (2)	C1B—H1BB	0.9700
C3—C4	1.364 (3)	C2B—C3B	1.4831 (19)
C3—H3A	0.9300	C3B—C4B	1.3910 (19)
C4—C5	1.370 (3)	C3B—C8B	1.3972 (18)
C4—H4A	0.9300	C4B—C5B	1.371 (2)
C5—C6	1.386 (2)	C4B—H4BA	0.9300
C5—H5A	0.9300	C5B—C6B	1.378 (2)
C6—H6A	0.9300	C5B—H5BA	0.9300
C1A—C2A	1.504 (2)	C6B—C7B	1.372 (2)
C1A—H1AA	0.9700	C7B—C8B	1.374 (2)
C1A—H1AB	0.9700	C7B—H7BA	0.9300
C2A—C3A	1.488 (2)	C8B—H8BA	0.9300
C3A—C4A	1.375 (2)

C1—C—C1A	112.96 (11)	C6A—C5A—C4A	119.09 (15)
C1—C—C1B	107.79 (11)	C6A—C5A—H5AA	120.5
C1A—C—C1B	110.64 (10)	C4A—C5A—H5AA	120.5
C1—C—H0A	108.4	C5A—C6A—C7A	121.53 (14)
C1A—C—H0A	108.4	C5A—C6A—Cl1A	120.38 (13)
C1B—C—H0A	108.4	C7A—C6A—Cl1A	118.08 (13)
C6—C1—C2	115.99 (13)	C6A—C7A—C8A	118.44 (15)
C6—C1—C	121.92 (12)	C6A—C7A—H7AA	120.8
C2—C1—C	121.97 (12)	C8A—C7A—H7AA	120.8
C3—C2—C1	122.17 (14)	C3A—C8A—C7A	121.32 (14)
C3—C2—Cl	117.63 (12)	C3A—C8A—H8AA	119.3
C1—C2—Cl	120.19 (11)	C7A—C8A—H8AA	119.3
C4—C3—C2	119.73 (16)	C2B—C1B—C	114.25 (11)
C4—C3—H3A	120.1	C2B—C1B—H1BA	108.7
C2—C3—H3A	120.1	C—C1B—H1BA	108.7
C3—C4—C5	120.13 (16)	C2B—C1B—H1BB	108.7
C3—C4—H4A	119.9	C—C1B—H1BB	108.7
C5—C4—H4A	119.9	H1BA—C1B—H1BB	107.6
C4—C5—C6	119.39 (16)	O1B—C2B—C3B	120.07 (12)
C4—C5—H5A	120.3	O1B—C2B—C1B	119.50 (13)
C6—C5—H5A	120.3	C3B—C2B—C1B	120.43 (11)
C1—C6—C5	122.57 (15)	C4B—C3B—C8B	118.21 (13)
C1—C6—H6A	118.7	C4B—C3B—C2B	119.49 (11)
C5—C6—H6A	118.7	C8B—C3B—C2B	122.30 (12)
C2A—C1A—C	114.47 (11)	C5B—C4B—C3B	121.13 (12)
C2A—C1A—H1AA	108.6	C5B—C4B—H4BA	119.4
C—C1A—H1AA	108.6	C3B—C4B—H4BA	119.4
C2A—C1A—H1AB	108.6	C4B—C5B—C6B	119.10 (13)
C—C1A—H1AB	108.6	C4B—C5B—H5BA	120.5
H1AA—C1A—H1AB	107.6	C6B—C5B—H5BA	120.5
O1A—C2A—C3A	121.13 (13)	C7B—C6B—C5B	121.52 (13)
O1A—C2A—C1A	120.22 (13)	C7B—C6B—Cl1B	119.20 (11)
C3A—C2A—C1A	118.61 (12)	C5B—C6B—Cl1B	119.28 (11)
C4A—C3A—C8A	118.37 (13)	C6B—C7B—C8B	119.09 (13)
C4A—C3A—C2A	119.48 (13)	C6B—C7B—H7BA	120.5
C8A—C3A—C2A	122.15 (12)	C8B—C7B—H7BA	120.5
C5A—C4A—C3A	121.23 (15)	C7B—C8B—C3B	120.94 (13)
C5A—C4A—H4AA	119.4	C7B—C8B—H8BA	119.5
C3A—C4A—H4AA	119.4	C3B—C8B—H8BA	119.5

C1A—C—C1—C6	38.87 (18)	C4A—C5A—C6A—C7A	1.0 (3)
C1B—C—C1—C6	−83.68 (15)	C4A—C5A—C6A—Cl1A	−179.63 (14)
C1A—C—C1—C2	−145.14 (12)	C5A—C6A—C7A—C8A	−0.9 (3)
C1B—C—C1—C2	92.31 (14)	Cl1A—C6A—C7A—C8A	179.71 (13)
C6—C1—C2—C3	−0.3 (2)	C4A—C3A—C8A—C7A	1.4 (2)
C—C1—C2—C3	−176.50 (13)	C2A—C3A—C8A—C7A	−177.85 (15)
C6—C1—C2—Cl	178.12 (11)	C6A—C7A—C8A—C3A	−0.3 (3)
C—C1—C2—Cl	1.90 (18)	C1—C—C1B—C2B	−177.57 (10)
C1—C2—C3—C4	−0.5 (2)	C1A—C—C1B—C2B	58.46 (15)
Cl—C2—C3—C4	−178.91 (13)	C—C1B—C2B—O1B	−95.04 (15)
C2—C3—C4—C5	0.3 (3)	C—C1B—C2B—C3B	84.40 (14)
C3—C4—C5—C6	0.7 (3)	O1B—C2B—C3B—C4B	−4.2 (2)
C2—C1—C6—C5	1.3 (2)	C1B—C2B—C3B—C4B	176.39 (11)
C—C1—C6—C5	177.49 (14)	O1B—C2B—C3B—C8B	176.04 (13)
C4—C5—C6—C1	−1.5 (3)	C1B—C2B—C3B—C8B	−3.40 (19)
C1—C—C1A—C2A	67.11 (15)	C8B—C3B—C4B—C5B	0.7 (2)
C1B—C—C1A—C2A	−171.94 (11)	C2B—C3B—C4B—C5B	−179.14 (13)
C—C1A—C2A—O1A	12.0 (2)	C3B—C4B—C5B—C6B	−0.9 (2)
C—C1A—C2A—C3A	−170.18 (12)	C4B—C5B—C6B—C7B	0.1 (2)
O1A—C2A—C3A—C4A	1.4 (2)	C4B—C5B—C6B—Cl1B	179.99 (11)
C1A—C2A—C3A—C4A	−176.42 (14)	C5B—C6B—C7B—C8B	1.1 (2)
O1A—C2A—C3A—C8A	−179.32 (16)	Cl1B—C6B—C7B—C8B	−178.87 (11)
C1A—C2A—C3A—C8A	2.9 (2)	C6B—C7B—C8B—C3B	−1.3 (2)
C8A—C3A—C4A—C5A	−1.4 (3)	C4B—C3B—C8B—C7B	0.5 (2)
C2A—C3A—C4A—C5A	177.96 (16)	C2B—C3B—C8B—C7B	−179.73 (13)
C3A—C4A—C5A—C6A	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···O1Aⁱ	0.93	2.50	3.306 (2)	145
C7B—H7BA···O1Bⁱⁱ	0.93	2.51	3.2917 (17)	142

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇Cl₃O₂
M_r	431.72
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1717 (8), 7.7000 (15), 18.901 (6)
α, β, γ (°)	85.88 (2), 83.518 (15), 77.656 (12)
V (Å³)	1011.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.45 × 0.39 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini R CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.712, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	14729, 6690, 3147
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 0.93
No. of reflections	6690
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.33

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.