1,1,1-Trichloro-2,2-bis­(4-eth­oxy­phen­yl)ethane

Smith, G.

doi:10.1107/S1600536812043826

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3219

doi:10.1107/S1600536812043826

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1,1,1-Trichloro-2,2-bis(4-ethoxyphenyl)ethane

Graham Smith ^a ^*

^aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 16 October 2012; accepted 22 October 2012; online 27 October 2012)

In the title compound, C₁₈H₁₉Cl₃O₂, which is the 4-ethoxyphenyl analogue of the insecticidally active 4-methoxyphenyl compound methoxychlor, the dihedral angle between the two benzene rings is 60.38 (13)°. An intramolecular aromatic C—H⋯Cl interaction is present.

Related literature

For background to DDT-type insecticides, see: Läuger et al. (1944 ). For unit-cell data for the title compound, see: Schneider & Fankuchen (1946 ). For the structures of analogous p-alkoxy-substituted DDT compounds, see: Smith et al. (1976 ); Smith (2012 ).

Experimental

Crystal data

C₁₈H₁₉Cl₃O₂
M_r = 373.68
Monoclinic, P 2₁ /c
a = 23.4405 (7) Å
b = 9.8835 (2) Å
c = 7.7924 (2) Å
β = 99.536 (3)°
V = 1780.35 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 200 K
0.30 × 0.15 × 0.08 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.960, T_max = 0.980
10942 measured reflections
3109 independent reflections
2282 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.092
S = 0.91
3109 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2B—H2B⋯Cl2	0.93	2.67	3.321 (3)	128

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ) within WinGX (Farrugia, 1999 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043826/lh5546sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043826/lh5546Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043826/lh5546Isup3.cml

checkCIF report

Comment top

The title compound, C₁₈H₁₉Cl₃0₂ is the 4-ethoxyphenyl analogue of the insecticides DDT [1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane] and methoxychlor (the 4-methoxyphenyl analogue), and has similar insecticidal activity (Läuger et al., 1944), but was not used as a commercial product. The crystal structures of methoxychlor (Smith et al., 1976) and the p-butoxy analogue (Smith, 2012) are known and the unit cell data for the title compound has been reported (Schneider & Fankuchen, 1946). The structure of the title compound is reported herein.

The molecular structure of the title compound is shown in Fig. 1. The unit cell and space group are consistent with those previously reported. The dihedral angle between the two benzene ring mean planes is 60.38 (13)°. The value of this angle is 77.7° (no s.u. available) in the structure of methoxychlor (Smith et al., 1976). The conformations of the two ethoxy side chains relative to their benzene rings (A and B) are similar [comparative torsion angles C3—C4—O4—C11, -173.3 (3) and 162.2 (2), respectively]. The B ring conformation is stabilized by an intramolecular aromatic C2B—H···Cl2 interaction (Table 1). No significant intermolecular interactions are present (Fig. 2).

Related literature top

For background to DDT-type insecticides, see: Läuger et al. (1944). For unit-cell data for the title compound, see: Schneider & Fankuchen (1946). For the structures of analogous p-alkoxy-substituted DDT compounds, see: Smith et al. (1976); Smith (2012).

Experimental top

The title compound was obtained as an analytical reference standard from the US Public Health Service. Colourless crystal prisms suitable for X-ray analysis were obtained by room temperature evaporation of a solution of the title compound in ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A perspective view of the crystal packing in the unit cell viewed approximately along the b axis.

1,1,1-Trichloro-2,2-bis(4-ethoxyphenyl)ethane top

Crystal data top

C₁₈H₁₉Cl₃O₂	F(000) = 776
M_r = 373.68	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3070 reflections
a = 23.4405 (7) Å	θ = 3.1–28.8°
b = 9.8835 (2) Å	µ = 0.52 mm⁻¹
c = 7.7924 (2) Å	T = 200 K
β = 99.536 (3)°	Prism, colourless
V = 1780.35 (8) Å³	0.30 × 0.15 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	3109 independent reflections
Radiation source: Enhance (Mo) X-ray source	2282 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
Detector resolution: 16.077 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ω scans	h = −27→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→11
T_min = 0.960, T_max = 0.980	l = −9→9
10942 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.013P)²] where P = (F_o² + 2F_c²)/3
3109 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₁₉Cl₃O₂	V = 1780.35 (8) Å³
M_r = 373.68	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 23.4405 (7) Å	µ = 0.52 mm⁻¹
b = 9.8835 (2) Å	T = 200 K
c = 7.7924 (2) Å	0.30 × 0.15 × 0.08 mm
β = 99.536 (3)°

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	3109 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2282 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.980	R_int = 0.106
10942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 0.91	Δρ_max = 0.38 e Å⁻³
3109 reflections	Δρ_min = −0.25 e Å⁻³
210 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.33099 (3)	−0.05016 (8)	0.40168 (9)	0.0385 (3)
Cl2	0.23442 (3)	−0.19217 (7)	0.50376 (9)	0.0374 (3)
Cl3	0.21520 (3)	0.01715 (8)	0.24488 (9)	0.0412 (3)
O4A	0.02901 (9)	0.0931 (2)	0.7508 (3)	0.0442 (8)
O4B	0.44289 (8)	0.0498 (2)	1.1563 (2)	0.0406 (7)
C1	0.25902 (12)	−0.0312 (3)	0.4447 (3)	0.0274 (9)
C1A	0.19612 (11)	0.0869 (3)	0.6338 (3)	0.0228 (9)
C1B	0.30558 (11)	0.0680 (3)	0.7397 (3)	0.0247 (9)
C2	0.25640 (11)	0.0785 (3)	0.5851 (3)	0.0240 (9)
C2A	0.17938 (12)	0.0081 (3)	0.7642 (3)	0.0293 (10)
C2B	0.31987 (12)	−0.0486 (3)	0.8366 (3)	0.0293 (9)
C3A	0.12369 (13)	0.0129 (3)	0.7994 (4)	0.0325 (10)
C3B	0.36559 (12)	−0.0512 (3)	0.9749 (4)	0.0322 (10)
C4A	0.08312 (12)	0.0979 (3)	0.7062 (4)	0.0304 (10)
C4B	0.39827 (12)	0.0635 (3)	1.0180 (3)	0.0301 (10)
C5A	0.09942 (12)	0.1816 (3)	0.5803 (3)	0.0316 (10)
C5B	0.38476 (12)	0.1820 (3)	0.9249 (3)	0.0314 (10)
C6A	0.15553 (12)	0.1748 (3)	0.5458 (3)	0.0291 (9)
C6B	0.33864 (12)	0.1830 (3)	0.7873 (3)	0.0273 (9)
C11A	−0.01660 (13)	0.1672 (3)	0.6474 (4)	0.0485 (11)
C11B	0.48754 (13)	0.1495 (3)	1.1746 (4)	0.0425 (11)
C21A	−0.07174 (14)	0.1329 (4)	0.7104 (5)	0.0641 (16)
C21B	0.53406 (13)	0.1062 (3)	1.3219 (4)	0.0509 (14)
H2	0.26230	0.16490	0.52880	0.0290*
H2A	0.20620	−0.04910	0.82900	0.0350*
H2B	0.29830	−0.12680	0.80820	0.0350*
H3A	0.11330	−0.04150	0.88660	0.0390*
H3B	0.37420	−0.13040	1.03840	0.0390*
H5A	0.07300	0.24180	0.51950	0.0380*
H5B	0.40630	0.26010	0.95420	0.0380*
H6A	0.16620	0.23110	0.46090	0.0350*
H6B	0.32970	0.26270	0.72540	0.0330*
H11A	−0.01930	0.14280	0.52580	0.0580*
H11B	0.47210	0.23700	1.20010	0.0510*
H12A	−0.00910	0.26360	0.65890	0.0580*
H12B	0.50340	0.15690	1.06760	0.0510*
H21A	−0.10340	0.17870	0.63990	0.0960*
H21B	0.56480	0.17140	1.33640	0.0760*
H22A	−0.06920	0.16110	0.82930	0.0960*
H22B	0.54890	0.01940	1.29560	0.0760*
H23A	−0.07800	0.03700	0.70230	0.0960*
H23B	0.51810	0.10010	1.42730	0.0760*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0348 (5)	0.0443 (5)	0.0374 (5)	0.0061 (4)	0.0093 (3)	−0.0034 (4)
Cl2	0.0452 (5)	0.0235 (4)	0.0428 (5)	−0.0032 (3)	0.0053 (4)	−0.0059 (3)
Cl3	0.0453 (5)	0.0481 (5)	0.0263 (4)	0.0079 (4)	−0.0054 (3)	−0.0015 (4)
O4A	0.0280 (13)	0.0556 (15)	0.0488 (14)	0.0015 (11)	0.0054 (10)	−0.0016 (11)
O4B	0.0327 (12)	0.0469 (14)	0.0373 (12)	−0.0064 (10)	−0.0081 (10)	0.0016 (10)
C1	0.0303 (17)	0.0255 (16)	0.0252 (15)	0.0056 (13)	0.0014 (13)	0.0001 (13)
C1A	0.0249 (16)	0.0193 (14)	0.0230 (15)	0.0016 (12)	0.0005 (12)	−0.0031 (12)
C1B	0.0250 (16)	0.0248 (15)	0.0244 (15)	0.0002 (13)	0.0044 (12)	0.0024 (13)
C2	0.0288 (16)	0.0162 (14)	0.0254 (15)	0.0014 (12)	−0.0003 (12)	0.0003 (12)
C2A	0.0333 (18)	0.0210 (15)	0.0316 (17)	0.0031 (13)	−0.0001 (14)	0.0034 (13)
C2B	0.0276 (17)	0.0269 (15)	0.0314 (17)	−0.0041 (13)	−0.0007 (13)	0.0021 (13)
C3A	0.0357 (18)	0.0270 (16)	0.0350 (18)	−0.0015 (14)	0.0062 (14)	0.0031 (14)
C3B	0.0337 (18)	0.0307 (17)	0.0315 (17)	0.0014 (14)	0.0030 (14)	0.0064 (14)
C4A	0.0262 (17)	0.0338 (17)	0.0303 (17)	−0.0023 (14)	0.0025 (14)	−0.0093 (14)
C4B	0.0289 (17)	0.0385 (18)	0.0219 (16)	0.0016 (14)	0.0014 (13)	−0.0041 (14)
C5A	0.0319 (18)	0.0286 (17)	0.0312 (17)	0.0052 (14)	−0.0036 (14)	0.0021 (14)
C5B	0.0306 (17)	0.0301 (17)	0.0328 (17)	−0.0063 (14)	0.0036 (14)	−0.0070 (14)
C6A	0.0347 (18)	0.0250 (15)	0.0262 (16)	−0.0008 (13)	0.0007 (13)	0.0023 (13)
C6B	0.0302 (17)	0.0251 (16)	0.0268 (16)	0.0010 (13)	0.0051 (13)	0.0018 (13)
C11A	0.0314 (19)	0.050 (2)	0.061 (2)	0.0063 (17)	−0.0013 (17)	−0.0054 (18)
C11B	0.0329 (19)	0.051 (2)	0.0425 (19)	−0.0057 (16)	0.0028 (15)	−0.0063 (16)
C21A	0.029 (2)	0.065 (3)	0.097 (3)	−0.0024 (19)	0.007 (2)	−0.013 (2)
C21B	0.033 (2)	0.066 (3)	0.048 (2)	−0.0009 (17)	−0.0103 (16)	−0.0111 (18)

Geometric parameters (Å, º) top

Cl1—C1	1.784 (3)	C11A—C21A	1.496 (5)
Cl2—C1	1.779 (3)	C11B—C21B	1.508 (4)
Cl3—C1	1.783 (3)	C2—H2	0.9800
O4A—C4A	1.370 (4)	C2A—H2A	0.9300
O4A—C11A	1.429 (4)	C2B—H2B	0.9300
O4B—C4B	1.379 (3)	C3A—H3A	0.9300
O4B—C11B	1.427 (4)	C3B—H3B	0.9300
C1—C2	1.549 (4)	C5A—H5A	0.9300
C1A—C2	1.525 (4)	C5B—H5B	0.9300
C1A—C2A	1.388 (4)	C6A—H6A	0.9300
C1A—C6A	1.384 (4)	C6B—H6B	0.9300
C1B—C2	1.527 (3)	C11A—H11A	0.9700
C1B—C2B	1.388 (4)	C11A—H12A	0.9700
C1B—C6B	1.391 (4)	C11B—H11B	0.9700
C2A—C3A	1.379 (4)	C11B—H12B	0.9700
C2B—C3B	1.389 (4)	C21A—H21A	0.9600
C3A—C4A	1.382 (4)	C21A—H22A	0.9600
C3B—C4B	1.378 (4)	C21A—H23A	0.9600
C4A—C5A	1.385 (4)	C21B—H21B	0.9600
C4B—C5B	1.386 (4)	C21B—H22B	0.9600
C5A—C6A	1.387 (4)	C21B—H23B	0.9600
C5B—C6B	1.391 (4)

C4A—O4A—C11A	118.5 (2)	C3A—C2A—H2A	119.00
C4B—O4B—C11B	117.3 (2)	C1B—C2B—H2B	119.00
Cl1—C1—Cl2	108.18 (16)	C3B—C2B—H2B	119.00
Cl1—C1—Cl3	106.86 (13)	C2A—C3A—H3A	120.00
Cl1—C1—C2	110.84 (19)	C4A—C3A—H3A	120.00
Cl2—C1—Cl3	107.53 (15)	C2B—C3B—H3B	120.00
Cl2—C1—C2	113.01 (18)	C4B—C3B—H3B	120.00
Cl3—C1—C2	110.17 (19)	C4A—C5A—H5A	120.00
C2—C1A—C2A	122.5 (2)	C6A—C5A—H5A	120.00
C2—C1A—C6A	120.0 (2)	C4B—C5B—H5B	120.00
C2A—C1A—C6A	117.4 (2)	C6B—C5B—H5B	120.00
C2—C1B—C2B	124.6 (3)	C1A—C6A—H6A	119.00
C2—C1B—C6B	118.0 (2)	C5A—C6A—H6A	119.00
C2B—C1B—C6B	117.4 (2)	C1B—C6B—H6B	119.00
C1—C2—C1A	111.2 (2)	C5B—C6B—H6B	119.00
C1—C2—C1B	113.4 (2)	O4A—C11A—H11A	110.00
C1A—C2—C1B	114.7 (2)	O4A—C11A—H12A	110.00
C1A—C2A—C3A	121.2 (3)	C21A—C11A—H11A	110.00
C1B—C2B—C3B	121.6 (3)	C21A—C11A—H12A	110.00
C2A—C3A—C4A	120.6 (3)	H11A—C11A—H12A	108.00
C2B—C3B—C4B	120.0 (3)	O4B—C11B—H11B	110.00
O4A—C4A—C3A	115.5 (3)	O4B—C11B—H12B	110.00
O4A—C4A—C5A	125.2 (3)	C21B—C11B—H11B	110.00
C3A—C4A—C5A	119.3 (3)	C21B—C11B—H12B	110.00
O4B—C4B—C3B	115.4 (2)	H11B—C11B—H12B	109.00
O4B—C4B—C5B	124.8 (3)	C11A—C21A—H21A	109.00
C3B—C4B—C5B	119.9 (2)	C11A—C21A—H22A	109.00
C4A—C5A—C6A	119.4 (3)	C11A—C21A—H23A	109.00
C4B—C5B—C6B	119.4 (3)	H21A—C21A—H22A	109.00
C1A—C6A—C5A	122.1 (2)	H21A—C21A—H23A	109.00
C1B—C6B—C5B	121.8 (3)	H22A—C21A—H23A	110.00
O4A—C11A—C21A	107.8 (3)	C11B—C21B—H21B	109.00
O4B—C11B—C21B	107.8 (2)	C11B—C21B—H22B	109.00
C1—C2—H2	106.00	C11B—C21B—H23B	110.00
C1A—C2—H2	106.00	H21B—C21B—H22B	109.00
C1B—C2—H2	106.00	H21B—C21B—H23B	109.00
C1A—C2A—H2A	119.00	H22B—C21B—H23B	109.00

C11A—O4A—C4A—C3A	−173.3 (3)	C2B—C1B—C2—C1	−52.8 (3)
C11A—O4A—C4A—C5A	8.0 (4)	C2B—C1B—C2—C1A	76.3 (3)
C4A—O4A—C11A—C21A	173.7 (3)	C6B—C1B—C2—C1	127.1 (3)
C11B—O4B—C4B—C3B	162.2 (2)	C6B—C1B—C2—C1A	−103.8 (3)
C11B—O4B—C4B—C5B	−18.4 (4)	C2—C1B—C2B—C3B	179.4 (3)
C4B—O4B—C11B—C21B	−174.3 (2)	C6B—C1B—C2B—C3B	−0.5 (4)
Cl1—C1—C2—C1A	−175.16 (18)	C2—C1B—C6B—C5B	−179.1 (2)
Cl1—C1—C2—C1B	−44.3 (3)	C2B—C1B—C6B—C5B	0.8 (4)
Cl2—C1—C2—C1A	−53.5 (3)	C1A—C2A—C3A—C4A	−0.7 (4)
Cl2—C1—C2—C1B	77.3 (3)	C1B—C2B—C3B—C4B	−0.5 (4)
Cl3—C1—C2—C1A	66.8 (2)	C2A—C3A—C4A—O4A	179.2 (3)
Cl3—C1—C2—C1B	−162.36 (19)	C2A—C3A—C4A—C5A	−2.0 (4)
C2A—C1A—C2—C1	88.5 (3)	C2B—C3B—C4B—O4B	−179.5 (2)
C2A—C1A—C2—C1B	−41.7 (4)	C2B—C3B—C4B—C5B	1.1 (4)
C6A—C1A—C2—C1	−91.0 (3)	O4A—C4A—C5A—C6A	−179.0 (3)
C6A—C1A—C2—C1B	138.9 (3)	C3A—C4A—C5A—C6A	2.4 (4)
C2—C1A—C2A—C3A	−176.7 (3)	O4B—C4B—C5B—C6B	179.9 (2)
C6A—C1A—C2A—C3A	2.8 (4)	C3B—C4B—C5B—C6B	−0.8 (4)
C2—C1A—C6A—C5A	177.1 (2)	C4A—C5A—C6A—C1A	−0.2 (4)
C2A—C1A—C6A—C5A	−2.4 (4)	C4B—C5B—C6B—C1B	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2B—H2B···Cl2	0.93	2.67	3.321 (3)	128

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉Cl₃O₂
M_r	373.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	23.4405 (7), 9.8835 (2), 7.7924 (2)
β (°)	99.536 (3)
V (Å³)	1780.35 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.30 × 0.15 × 0.08

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.960, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10942, 3109, 2282
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.092, 0.91
No. of reflections	3109
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.25

Computer programs: CrysAlis PRO (Agilent, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2B—H2B···Cl2	0.93	2.67	3.321 (3)	128

Acknowledgements

The author acknowledges financial support from the Australian Research Council and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

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