Bis(1,3-dibenzyl­imidazolium) μ-oxido-bis­[trichloridoferrate(III)]

Mutambi, E.M.; Adams, C.J.; Orpen, A.G.

doi:10.1107/S1600536810024098

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m846

doi:10.1107/S1600536810024098

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Bis(1,3-dibenzylimidazolium) μ-oxido-bis[trichloridoferrate(III)]

E. M. Mutambi,^a ^* C. J. Adams ^a and A. G. Orpen ^a

^aUniversity of Bristol, School of Chemistry, Cantock's Close, Bristol BS8 1TS, England
^*Correspondence e-mail: chemm@bristol.ac.uk

(Received 7 June 2010; accepted 21 June 2010; online 26 June 2010)

In the title compound (C₁₇H₁₇N₂)₂[Fe₂Cl₆O], obtained from the solid-state reaction of FeCl₂ and N,N′-dibenzylimidazolium chloride, the complex anion has approximate D_3d symmetry with crystallographically imposed inversion symmetry coincident with the bridging μ-O atom. The stereochemistry about each FeCl₃O centre is distorted tetrahedral [Fe—Cl = 2.2176 (5)–2.2427 (5) Å and Fe—O = 1.7545 (2) Å]. The Cl atoms are involved in weak anion–cation C—H⋯Cl interactions, giving a network structure.

Related literature

For literature relating to the intended product, see: Yoshida et al. (2005 ); Zhong et al. (2007 ). For literature relating to anions see: Molins et al. (1998 ); Kohn et al. (1996 ); Vasilevsky et al. (1988 ).

Experimental

Crystal data

(C₁₇H₁₇N₂)₂[Fe₂Cl₆O]
M_r = 839.05
Orthorhombic, P b c a
a = 16.2468 (5) Å
b = 12.8841 (4) Å
c = 17.6041 (5) Å
V = 3684.99 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 100 K
0.31 × 0.21 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.681, T_max = 0.815
42672 measured reflections
5399 independent reflections
4111 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.081
S = 1.04
5399 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1ⁱ	0.95	2.82	3.6579 (16)	147
C3—H3⋯Cl1	0.95	2.81	3.4853 (17)	129
C11—H11A⋯Cl1ⁱ	0.99	2.85	3.7440 (18)	151
C13—H13⋯Cl2ⁱⁱ	0.95	2.86	3.5619 (18)	131
C15—H15⋯Cl2ⁱⁱⁱ	0.95	2.91	3.8403 (18)	167
C2—H2⋯Cl3	0.95	2.91	3.8223 (17)	162
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024098/zs2046sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024098/zs2046Isup2.hkl

checkCIF report

Comment top

We sought to widen the synthetic routes for the synthesis of [FeCl₄]^-–[HIBz]⁺ compounds (IBz = N,N'-dibenzylimidazole) by using solid state reactions without resorting to solution methods. The aim was to form the salts by grinding together the reactants and this was done with FeCl₂ and IBz.HCl resulting in formation of the title compound (C₁₇H₁₇N₂)₂ [Cl₆Fe₂O] (I), which was obtained during the recrystallization process after extracting with dichloromethane and the structure is reported here. The asymmetric unit of (I) contains one HIBz⁺ cation and half of [Fe₂OCl₆]^2- dianion has D₃_d symmetry with crystallographically imposed inversion symmetry coincident with the bridging O atom (Fig. 1). The stereochemistry about each FeCl₃O centre is tetrahedral [Fe–Cl, 2.2176 (5)–2.2427 (5) Å: Fe–O, 1.7545 (2) Å]. The Fe—O bond distance compares very well with the average bond length of 1.758 Å for similar anions reported in the CSD. However, the Fe—Cl bond distances are slightly longer compared to the mean Fe—Cl distance of 2.181 Å in the tetrahedral FeCl₄, but agree well with the average distance of 2.214 Å reported in the CSD for anions similar to (I). In the cation the phenyl rings lie approximately perpendicular to the plane of the HIBz ring [torsion angles C1–N1–C4–C5, 86.90 (19)°; C1–N2–C11–C12, 109.17 (18)°].

The crystal structure shows weak cation–anion C—H···Cl hydrogen-bonding interactions (Table 1, Fig. 2), giving a network structure (Figure 3).

Related literature top

For literature relating to the intended product, see: Yoshida et al. (2005); Zhong et al. (2007). For literature relating to anions see: Molins et al. (1998); Kohn et al. (1996); Vasilevsky et al. (1988).

Experimental top

FeCl₂ (0.0299 g: 0.1 mmol) and N,N'-dibenzylimidazolium chloride (0.0858 g: 0.2 mmol) were ground together for ca. 10 minutes using a mortar and pestle. A small amount of the crystalline product was dissolved in dichloromethane and allowed to slowly evaporate at room temperature, giving after 3 days, yellow plate-like crystals of (I) suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure and atom numbering scheme for the IBz cation and the complex dianion in (I). The dianion lies across an inversion centre: for primed atoms, the symmetry code is -x + 1, -y, -z + 2. Non-H atoms are drawn at the 50% probability level.
	Fig. 2. Cation–anion C—H···Cl interactions in (I).
	Fig. 3. Crystal packing showing the three-dimensional networks formed in (I).

Bis(1,3-dibenzylimidazolium) µ-oxido-bis[trichloridoferrate(III)] top

Crystal data top

(C₁₇H₁₇N₂)₂[Fe₂Cl₆O]	F(000) = 1712
M_r = 839.05	D_x = 1.512 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8129 reflections
a = 16.2468 (5) Å	θ = 2.3–29.0°
b = 12.8841 (4) Å	µ = 1.26 mm⁻¹
c = 17.6041 (5) Å	T = 100 K
V = 3684.99 (19) Å³	Plate, yellow
Z = 4	0.31 × 0.21 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5399 independent reflections
Radiation source: sealed tube	4111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 9.091 pixels mm^-1	θ_max = 30.1°, θ_min = 3.4°
ϕ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→18
T_min = 0.681, T_max = 0.815	l = −24→24
42672 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0331P)² + 1.977P] where P = (F_o² + 2F_c²)/3
5399 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

(C₁₇H₁₇N₂)₂[Fe₂Cl₆O]	V = 3684.99 (19) Å³
M_r = 839.05	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 16.2468 (5) Å	µ = 1.26 mm⁻¹
b = 12.8841 (4) Å	T = 100 K
c = 17.6041 (5) Å	0.31 × 0.21 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5399 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4111 reflections with I > 2σ(I)
T_min = 0.681, T_max = 0.815	R_int = 0.052
42672 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.04	Δρ_max = 0.77 e Å⁻³
5399 reflections	Δρ_min = −0.44 e Å⁻³
214 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
Fe1	0.572901 (17)	0.002174 (18)	0.926492 (14)	0.01778 (7)
N1	0.69781 (9)	0.34450 (10)	0.70045 (8)	0.0158 (3)
N2	0.60555 (9)	0.24363 (10)	0.65187 (8)	0.0162 (3)
C1	0.65919 (11)	0.31864 (12)	0.63681 (9)	0.0168 (3)
H1	0.6684	0.3489	0.5883	0.020*
C2	0.60972 (11)	0.22098 (13)	0.72855 (9)	0.0191 (3)
H2	0.5782	0.1704	0.7550	0.023*
C3	0.66719 (11)	0.28445 (13)	0.75867 (9)	0.0191 (3)
H3	0.6835	0.2872	0.8105	0.023*
C4	0.75812 (11)	0.42987 (12)	0.70917 (9)	0.0180 (3)
H4A	0.7904	0.4374	0.6618	0.022*
H4B	0.7967	0.4132	0.7509	0.022*
C5	0.71438 (11)	0.53029 (12)	0.72638 (9)	0.0158 (3)
C6	0.70433 (11)	0.56215 (13)	0.80122 (10)	0.0192 (3)
H6	0.7271	0.5220	0.8413	0.023*
C7	0.66112 (12)	0.65228 (14)	0.81769 (11)	0.0255 (4)
H7	0.6553	0.6744	0.8689	0.031*
C8	0.62652 (12)	0.70995 (14)	0.75939 (12)	0.0283 (4)
H8	0.5958	0.7708	0.7706	0.034*
C9	0.63691 (13)	0.67870 (14)	0.68495 (12)	0.0289 (4)
H9	0.6136	0.7186	0.6450	0.035*
C10	0.68116 (12)	0.58936 (14)	0.66809 (10)	0.0226 (4)
H10	0.6887	0.5688	0.6167	0.027*
C11	0.54927 (11)	0.19507 (13)	0.59652 (10)	0.0182 (3)
H11A	0.5494	0.2364	0.5491	0.022*
H11B	0.4926	0.1961	0.6173	0.022*
C12	0.57281 (11)	0.08439 (12)	0.57817 (9)	0.0159 (3)
C13	0.64112 (11)	0.06417 (13)	0.53308 (9)	0.0185 (3)
H13	0.6745	0.1199	0.5158	0.022*
C14	0.66090 (12)	−0.03689 (14)	0.51314 (9)	0.0209 (4)
H14	0.7082	−0.0503	0.4829	0.025*
C15	0.61153 (12)	−0.11859 (13)	0.53742 (10)	0.0219 (4)
H15	0.6244	−0.1877	0.5228	0.026*
C16	0.54355 (12)	−0.09921 (14)	0.58294 (10)	0.0213 (4)
H16	0.5102	−0.1551	0.5999	0.026*
C17	0.52421 (12)	0.00244 (13)	0.60382 (10)	0.0184 (3)
H17	0.4780	0.0157	0.6354	0.022*
Cl1	0.63474 (3)	0.15767 (3)	0.93098 (2)	0.02198 (10)
Cl2	0.66715 (3)	−0.12117 (3)	0.94427 (3)	0.02821 (11)
Cl3	0.51889 (3)	−0.02728 (3)	0.81283 (3)	0.02493 (10)
O4	0.5000	0.0000	1.0000	0.0421 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02114 (14)	0.01791 (12)	0.01430 (12)	−0.00244 (9)	0.00495 (10)	0.00096 (8)
N1	0.0180 (8)	0.0140 (6)	0.0153 (6)	0.0019 (5)	0.0011 (6)	−0.0013 (5)
N2	0.0190 (8)	0.0135 (6)	0.0160 (6)	0.0021 (5)	0.0017 (6)	−0.0007 (5)
C1	0.0204 (9)	0.0156 (7)	0.0144 (7)	0.0025 (6)	0.0018 (7)	0.0000 (6)
C2	0.0234 (10)	0.0164 (8)	0.0174 (8)	0.0015 (7)	0.0040 (7)	0.0035 (6)
C3	0.0252 (10)	0.0170 (8)	0.0151 (7)	0.0038 (7)	0.0017 (7)	0.0026 (6)
C4	0.0169 (9)	0.0170 (8)	0.0202 (8)	−0.0002 (6)	0.0008 (7)	−0.0017 (6)
C5	0.0147 (8)	0.0145 (7)	0.0182 (8)	−0.0022 (6)	0.0011 (6)	0.0006 (6)
C6	0.0189 (9)	0.0187 (8)	0.0200 (8)	−0.0023 (6)	0.0013 (7)	0.0001 (6)
C7	0.0246 (10)	0.0211 (9)	0.0308 (10)	−0.0048 (7)	0.0083 (8)	−0.0076 (7)
C8	0.0206 (10)	0.0137 (8)	0.0506 (12)	−0.0014 (7)	0.0110 (9)	−0.0004 (8)
C9	0.0252 (11)	0.0218 (9)	0.0397 (11)	0.0013 (7)	0.0011 (9)	0.0168 (8)
C10	0.0251 (10)	0.0222 (9)	0.0204 (8)	−0.0006 (7)	0.0022 (7)	0.0058 (6)
C11	0.0173 (9)	0.0170 (8)	0.0202 (8)	0.0001 (6)	−0.0016 (7)	−0.0014 (6)
C12	0.0179 (9)	0.0155 (7)	0.0144 (7)	0.0020 (6)	−0.0029 (7)	−0.0002 (5)
C13	0.0191 (9)	0.0206 (8)	0.0159 (7)	−0.0007 (7)	−0.0012 (7)	0.0012 (6)
C14	0.0224 (10)	0.0255 (9)	0.0148 (8)	0.0065 (7)	−0.0015 (7)	−0.0010 (6)
C15	0.0297 (11)	0.0196 (8)	0.0163 (8)	0.0058 (7)	−0.0071 (7)	−0.0024 (6)
C16	0.0250 (10)	0.0182 (8)	0.0208 (8)	−0.0020 (7)	−0.0053 (7)	0.0027 (6)
C17	0.0189 (9)	0.0203 (8)	0.0160 (7)	0.0015 (7)	−0.0016 (7)	0.0006 (6)
Cl1	0.0318 (3)	0.01609 (19)	0.01806 (19)	−0.00222 (16)	0.00283 (17)	−0.00090 (14)
Cl2	0.0343 (3)	0.0168 (2)	0.0335 (2)	−0.00020 (18)	−0.0127 (2)	0.00265 (16)
Cl3	0.0263 (2)	0.0239 (2)	0.0246 (2)	0.00011 (17)	−0.00685 (19)	−0.00070 (16)
O4	0.0488 (15)	0.0435 (13)	0.0342 (12)	−0.0089 (10)	0.0261 (11)	−0.0015 (9)

Geometric parameters (Å, º) top

Fe1—O4	1.7545 (2)	C7—H7	0.9500
Fe1—Cl3	2.2176 (5)	C8—C9	1.381 (3)
Fe1—Cl2	2.2290 (5)	C8—H8	0.9500
Fe1—Cl1	2.2427 (5)	C9—C10	1.389 (3)
N1—C1	1.327 (2)	C9—H9	0.9500
N1—C3	1.377 (2)	C10—H10	0.9500
N1—C4	1.481 (2)	C11—C12	1.511 (2)
N2—C1	1.328 (2)	C11—H11A	0.9900
N2—C2	1.383 (2)	C11—H11B	0.9900
N2—C11	1.476 (2)	C12—C13	1.389 (2)
C1—H1	0.9500	C12—C17	1.394 (2)
C2—C3	1.350 (2)	C13—C14	1.386 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.391 (3)
C4—C5	1.507 (2)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.387 (3)
C4—H4B	0.9900	C15—H15	0.9500
C5—C10	1.387 (2)	C16—C17	1.396 (2)
C5—C6	1.390 (2)	C16—H16	0.9500
C6—C7	1.387 (2)	C17—H17	0.9500
C6—H6	0.9500	O4—Fe1ⁱ	1.7545 (2)
C7—C8	1.386 (3)

O4—Fe1—Cl3	113.304 (18)	C9—C8—C7	119.78 (17)
O4—Fe1—Cl2	110.417 (18)	C9—C8—H8	120.1
O4—Fe1—Cl1	106.901 (16)	C7—C8—H8	120.1
Cl3—Fe1—Cl1	111.221 (19)	C8—C9—C10	120.49 (17)
Cl2—Fe1—Cl1	108.92 (2)	C8—C9—H9	119.8
C1—N1—C3	108.45 (14)	C10—C9—H9	119.8
C1—N1—C4	125.94 (14)	C5—C10—C9	119.86 (17)
C3—N1—C4	125.39 (14)	C5—C10—H10	120.1
C1—N2—C2	108.44 (14)	C9—C10—H10	120.1
C1—N2—C11	125.69 (14)	N2—C11—C12	112.61 (14)
C2—N2—C11	125.84 (15)	N2—C11—H11A	109.1
N1—C1—N2	108.93 (14)	C12—C11—H11A	109.1
N1—C1—H1	125.5	N2—C11—H11B	109.1
N2—C1—H1	125.5	C12—C11—H11B	109.1
C3—C2—N2	106.84 (15)	H11A—C11—H11B	107.8
C3—C2—H2	126.6	C13—C12—C17	119.72 (15)
N2—C2—H2	126.6	C13—C12—C11	120.09 (15)
C2—C3—N1	107.33 (15)	C17—C12—C11	120.14 (16)
C2—C3—H3	126.3	C14—C13—C12	120.40 (16)
N1—C3—H3	126.3	C14—C13—H13	119.8
N1—C4—C5	110.28 (14)	C12—C13—H13	119.8
N1—C4—H4A	109.6	C13—C14—C15	119.96 (17)
C5—C4—H4A	109.6	C13—C14—H14	120.0
N1—C4—H4B	109.6	C15—C14—H14	120.0
C5—C4—H4B	109.6	C16—C15—C14	120.04 (16)
H4A—C4—H4B	108.1	C16—C15—H15	120.0
C10—C5—C6	119.58 (16)	C14—C15—H15	120.0
C10—C5—C4	120.39 (15)	C15—C16—C17	120.01 (17)
C6—C5—C4	119.98 (15)	C15—C16—H16	120.0
C7—C6—C5	120.31 (17)	C17—C16—H16	120.0
C7—C6—H6	119.8	C12—C17—C16	119.86 (17)
C5—C6—H6	119.8	C12—C17—H17	120.1
C8—C7—C6	119.95 (17)	C16—C17—H17	120.1
C8—C7—H7	120.0	Fe1—O4—Fe1ⁱ	180.0
C6—C7—H7	120.0

C3—N1—C1—N2	−0.60 (19)	C7—C8—C9—C10	0.6 (3)
C4—N1—C1—N2	−175.46 (14)	C6—C5—C10—C9	−1.2 (3)
C2—N2—C1—N1	0.37 (19)	C4—C5—C10—C9	176.32 (17)
C11—N2—C1—N1	178.63 (14)	C8—C9—C10—C5	0.8 (3)
C1—N2—C2—C3	0.01 (19)	C1—N2—C11—C12	109.77 (18)
C11—N2—C2—C3	−178.25 (15)	C2—N2—C11—C12	−72.3 (2)
N2—C2—C3—N1	−0.37 (19)	N2—C11—C12—C13	−73.19 (19)
C1—N1—C3—C2	0.60 (19)	N2—C11—C12—C17	109.41 (18)
C4—N1—C3—C2	175.50 (15)	C17—C12—C13—C14	0.4 (2)
C1—N1—C4—C5	86.90 (19)	C11—C12—C13—C14	−177.04 (15)
C3—N1—C4—C5	−87.12 (19)	C12—C13—C14—C15	0.9 (3)
N1—C4—C5—C10	−82.77 (19)	C13—C14—C15—C16	−1.4 (3)
N1—C4—C5—C6	94.71 (18)	C14—C15—C16—C17	0.6 (3)
C10—C5—C6—C7	0.2 (3)	C13—C12—C17—C16	−1.2 (3)
C4—C5—C6—C7	−177.29 (16)	C11—C12—C17—C16	176.24 (15)
C5—C6—C7—C8	1.1 (3)	C15—C16—C17—C12	0.7 (3)
C6—C7—C8—C9	−1.5 (3)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1ⁱⁱ	0.95	2.82	3.6579 (16)	147
C3—H3···Cl1	0.95	2.81	3.4853 (17)	129
C11—H11A···Cl1ⁱⁱ	0.99	2.85	3.7440 (18)	151
C13—H13···Cl2ⁱⁱⁱ	0.95	2.86	3.5619 (18)	131
C15—H15···Cl2^iv	0.95	2.91	3.8403 (18)	167
C2—H2···Cl3	0.95	2.91	3.8223 (17)	162

Symmetry codes: (ii) x, −y+1/2, z−1/2; (iii) −x+3/2, −y, z−1/2; (iv) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	(C₁₇H₁₇N₂)₂[Fe₂Cl₆O]
M_r	839.05
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	16.2468 (5), 12.8841 (4), 17.6041 (5)
V (Å³)	3684.99 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.31 × 0.21 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.681, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	42672, 5399, 4111
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.081, 1.04
No. of reflections	5399
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.44

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1ⁱ	0.95	2.82	3.6579 (16)	147
C3—H3···Cl1	0.95	2.81	3.4853 (17)	129
C11—H11A···Cl1ⁱ	0.99	2.85	3.7440 (18)	151
C13—H13···Cl2ⁱⁱ	0.95	2.86	3.5619 (18)	131
C15—H15···Cl2ⁱⁱⁱ	0.95	2.91	3.8403 (18)	167
C2—H2···Cl3	0.95	2.91	3.8223 (17)	162

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+3/2, −y, z−1/2; (iii) x, −y−1/2, z−1/2.

Acknowledgements

EMM thanks the University of Bristol and Overseas Research Scholarship Awards Scheme (ORSAS) for funding.

References

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