3-Chloro­anilinium 4-methyl­benzene­sulfonate

Jasinski, J.P.; Golen, J.A.; Praveen, A.S.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536811041043

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2925

doi:10.1107/S1600536811041043

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3-Chloroanilinium 4-methylbenzenesulfonate

Jerry P. Jasinski,^a ^* James A. Golen,^a A. S. Praveen,^b H. S. Yathirajan ^b and B. Narayana ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 5 September 2011; accepted 5 October 2011; online 12 October 2011)

In the crystal structure of the title salt, C₆H₇ClN⁺·C₇H₇O₃S⁻, the cations and anions are linked via N—H⋯O hydrogen bonds into doubled chains in [010]. Weak intermolecular C—H⋯π interactions further link these chains into layers parallel to the bc plane.

Related literature

For background to molecular-ionic compounds, see: Czupinski et al. (2002 ); Katrusiak & Szafranski (2006 ). For related structures, see: Chanawanno et al. (2009 ); Chantrapromma et al. (2010 ); Collier et al. (2006 ); Fun et al. (2010 ); Li et al. (2005 ); Lin (2010 ); Tabatabaee & Noozari (2011 ); Wu et al. (2009 ). For normal bond lengths in organic compounds, see: Allen et al. (1987 ).

Experimental

Crystal data

C₆H₇ClN⁺·C₇H₇O₃S⁻
M_r = 299.76
Monoclinic, P 2₁ /c
a = 12.7848 (3) Å
b = 6.7767 (2) Å
c = 16.1702 (4) Å
β = 105.081 (2)°
V = 1352.71 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 298 K
0.32 × 0.26 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.872, T_max = 0.917
10965 measured reflections
3222 independent reflections
2723 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.109
S = 1.02
3222 reflections
182 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O1ⁱ	0.92 (1)	1.86 (1)	2.7640 (19)	168 (2)
N1—H1NC⋯O3ⁱⁱ	0.93 (1)	1.87 (1)	2.7806 (18)	166 (2)
N1—H1NB⋯O2	0.93 (1)	1.92 (1)	2.8282 (19)	167 (2)
C12—H12A⋯Cg1ⁱⁱⁱ	0.93	2.76	3.267 (2)	115
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041043/cv5151sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041043/cv5151Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041043/cv5151Isup3.cml

checkCIF report

Comment top

Recently much attention has been devoted to simple molecular-ionic crystals containing organic cations and anions due to the tunability of their special structural features and their interesting physical properties (Czupinski et al., 2002; Katrusiak & Szafranski, 2006). A variety of pharmaceutical drugs are prepared as salts of benzenesulfonic acid and are known as besylates. Crystal structures of some benzenesulfonate derivatives, viz., 2,4,6-triamino-1,3,5-triazin-1-ium 4-methylbenzenesulfonate monohydrate (Li et al., 2005), ephedrine besylate (Collier et al., 2006), 2-ethyl-6-methylanilinium 4-methylbenzenesulfonate (Wu et al., 2009), 2-[(E)-2-(4-ethoxyphenyl)ethenyl]-1-methylpyridinium 4-methylbenzenesulfonate monohydrate (Chanawanno et al., 2009), 2-aminopyrimidin-1-ium 4-methylbenzenesulfonate (Tabatabaee & Noozari, 2011), 4-(cyanomethyl)anilinium 4-methylbenzenesulfonate monohydrate (Lin, 2010), 1-methyl-2-[(E)-2-(2-thienyl)etheny] quinolinium 4-bromobenzenesulfonate (Fun et al., 2010) and (E)-2-[4-(dimethylamino)styryl]-1-methylpyridinium 4-methylbenzenesulfonate monohydrate (Chantrapromma et al., 2010) have been reported. In view of the importance of benzenesulphonic acid, we report herein the crystal structure of the title compound (I).

In the crystal structure of the title salt, C₆H₇ClN⁺. C₇H₇O₃S^- (Fig. 1), the cations and anions are linked via N—H···O hydrogen bonds into doubled chains in [010]. Weak intermolecular C—H···π interactions (Table 1) link further these chains into layers parallel to the bc plane.

Related literature top

For background to molecular-ionic compounds, see: Czupinski et al. (2002); Katrusiak & Szafranski (2006). For related structures, see: Chanawanno et al. (2009); Chantrapromma et al. (2010); Collier et al. (2006); Fun et al. (2010); Li et al. (2005); Lin (2010); Tabatabaee & Noozari (2011); Wu et al. (2009). For normal bond lengths in organic compounds, see: Allen et al. (1987).

Experimental top

To a stirred solution of 3-chloroaniline (0.67 g, 5.25 mmol) in methanol (15 ml), 4-methylbenzenesulfonic acid monohydrate (1g, 5.25 mmol ) was added, stirred at 323 K for 10 minutes and cooled to room temperature to afford the title compound (I). The single crystal was grown from methanol by slow evaporation method (M.P.: 538-540 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.

3-Chloroanilinium 4-methylbenzenesulfonate top

Crystal data top

C₆H₇ClN⁺·C₇H₇O₃S⁻	F(000) = 624
M_r = 299.76	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4281 reflections
a = 12.7848 (3) Å	θ = 3.2–30.0°
b = 6.7767 (2) Å	µ = 0.44 mm⁻¹
c = 16.1702 (4) Å	T = 298 K
β = 105.081 (2)°	Block, colourless
V = 1352.71 (6) Å³	0.32 × 0.26 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3222 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2723 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 16.1500 pixels mm^-1	θ_max = 27.9°, θ_min = 3.3°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −8→8
T_min = 0.872, T_max = 0.917	l = −21→18
10965 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0571P)² + 0.4988P] where P = (F_o² + 2F_c²)/3
3222 reflections	(Δ/σ)_max = 0.016
182 parameters	Δρ_max = 0.38 e Å⁻³
6 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₆H₇ClN⁺·C₇H₇O₃S⁻	V = 1352.71 (6) Å³
M_r = 299.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7848 (3) Å	µ = 0.44 mm⁻¹
b = 6.7767 (2) Å	T = 298 K
c = 16.1702 (4) Å	0.32 × 0.26 × 0.20 mm
β = 105.081 (2)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3222 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2723 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.917	R_int = 0.020
10965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.38 e Å⁻³
3222 reflections	Δρ_min = −0.47 e Å⁻³
182 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.71334 (3)	0.24308 (5)	0.57609 (2)	0.03033 (13)
Cl1	0.48393 (5)	0.72176 (8)	0.12500 (3)	0.05637 (17)
O1	0.60656 (10)	0.2751 (3)	0.58758 (10)	0.0679 (5)
O2	0.74597 (11)	0.4022 (2)	0.52892 (8)	0.0533 (4)
O3	0.72546 (12)	0.0520 (2)	0.54113 (9)	0.0589 (4)
N1	0.61726 (11)	0.7273 (2)	0.45378 (9)	0.0314 (3)
H1NC	0.6457 (12)	0.8338 (18)	0.4885 (10)	0.038*
H1NB	0.6507 (12)	0.6166 (17)	0.4825 (10)	0.038*
H1NA	0.5440 (7)	0.721 (2)	0.4477 (12)	0.038*
C1	0.80291 (12)	0.2481 (2)	0.67983 (10)	0.0277 (3)
C2	0.90883 (13)	0.3131 (2)	0.69108 (11)	0.0345 (3)
H2A	0.9330	0.3532	0.6442	0.041*
C3	0.97806 (13)	0.3175 (3)	0.77261 (12)	0.0403 (4)
H3A	1.0489	0.3612	0.7800	0.048*
C4	0.94414 (16)	0.2583 (2)	0.84357 (12)	0.0421 (4)
C5	0.83782 (16)	0.1937 (3)	0.83099 (11)	0.0430 (4)
H5A	0.8137	0.1532	0.8778	0.052*
C6	0.76757 (14)	0.1887 (2)	0.74998 (10)	0.0356 (3)
H6A	0.6967	0.1456	0.7426	0.043*
C7	1.0204 (2)	0.2665 (3)	0.93256 (15)	0.0687 (7)
H7A	1.0613	0.3869	0.9391	0.103*
H7B	1.0690	0.1560	0.9406	0.103*
H7C	0.9792	0.2618	0.9744	0.103*
C8	0.58589 (15)	0.7473 (2)	0.21912 (10)	0.0347 (4)
C9	0.56033 (13)	0.7206 (2)	0.29641 (10)	0.0312 (3)
H9A	0.4907	0.6851	0.2983	0.037*
C10	0.64148 (12)	0.7483 (2)	0.37058 (10)	0.0271 (3)
C11	0.74566 (13)	0.7990 (2)	0.36897 (11)	0.0348 (3)
H11A	0.7992	0.8178	0.4196	0.042*
C12	0.76860 (15)	0.8212 (3)	0.29072 (12)	0.0412 (4)
H12A	0.8387	0.8532	0.2888	0.049*
C13	0.68918 (16)	0.7965 (2)	0.21532 (11)	0.0414 (4)
H13A	0.7050	0.8128	0.1628	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0291 (2)	0.0332 (2)	0.0253 (2)	0.00048 (14)	0.00097 (14)	−0.00304 (13)
Cl1	0.0735 (4)	0.0580 (3)	0.0257 (2)	−0.0038 (2)	−0.0086 (2)	−0.00145 (18)
O1	0.0290 (7)	0.1261 (15)	0.0437 (8)	0.0078 (7)	0.0005 (6)	−0.0142 (8)
O2	0.0579 (8)	0.0538 (8)	0.0393 (7)	−0.0066 (6)	−0.0031 (6)	0.0160 (6)
O3	0.0771 (10)	0.0408 (7)	0.0450 (8)	0.0047 (7)	−0.0089 (7)	−0.0176 (6)
N1	0.0340 (7)	0.0355 (7)	0.0231 (6)	0.0001 (5)	0.0046 (5)	−0.0005 (5)
C1	0.0287 (7)	0.0251 (7)	0.0262 (7)	0.0009 (5)	0.0019 (6)	−0.0020 (5)
C2	0.0303 (8)	0.0347 (8)	0.0374 (8)	−0.0004 (6)	0.0068 (6)	−0.0022 (7)
C3	0.0297 (8)	0.0361 (8)	0.0480 (10)	0.0004 (7)	−0.0026 (7)	−0.0085 (7)
C4	0.0492 (10)	0.0313 (8)	0.0356 (9)	0.0063 (7)	−0.0073 (8)	−0.0051 (6)
C5	0.0594 (11)	0.0369 (9)	0.0302 (8)	−0.0026 (8)	0.0074 (8)	0.0037 (7)
C6	0.0378 (8)	0.0322 (8)	0.0353 (8)	−0.0061 (7)	0.0072 (7)	0.0015 (6)
C7	0.0792 (16)	0.0634 (14)	0.0436 (13)	0.0091 (11)	−0.0198 (11)	−0.0108 (9)
C8	0.0475 (9)	0.0283 (8)	0.0236 (7)	0.0016 (7)	0.0009 (6)	−0.0006 (5)
C9	0.0342 (8)	0.0300 (8)	0.0267 (7)	0.0002 (6)	0.0031 (6)	−0.0010 (6)
C10	0.0325 (7)	0.0239 (7)	0.0236 (7)	0.0025 (5)	0.0052 (6)	0.0008 (5)
C11	0.0345 (8)	0.0342 (8)	0.0329 (8)	−0.0021 (6)	0.0035 (6)	−0.0020 (6)
C12	0.0419 (9)	0.0392 (9)	0.0467 (10)	−0.0064 (7)	0.0189 (8)	−0.0009 (8)
C13	0.0625 (11)	0.0333 (8)	0.0320 (8)	−0.0050 (8)	0.0187 (8)	0.0015 (7)

Geometric parameters (Å, º) top

S1—O3	1.4374 (13)	C5—C6	1.382 (2)
S1—O2	1.4437 (13)	C5—H5A	0.9300
S1—O1	1.4413 (14)	C6—H6A	0.9300
S1—C1	1.7682 (15)	C7—H7A	0.9600
Cl1—C8	1.7359 (17)	C7—H7B	0.9600
N1—C10	1.464 (2)	C7—H7C	0.9600
N1—H1NC	0.928 (9)	C8—C9	1.383 (2)
N1—H1NB	0.927 (8)	C8—C13	1.379 (3)
N1—H1NA	0.916 (9)	C9—C10	1.379 (2)
C1—C6	1.386 (2)	C9—H9A	0.9300
C1—C2	1.390 (2)	C10—C11	1.382 (2)
C2—C3	1.384 (2)	C11—C12	1.379 (2)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.387 (3)	C12—C13	1.379 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.392 (3)	C13—H13A	0.9300
C4—C7	1.515 (3)

O3—S1—O2	112.92 (9)	C1—C6—C5	119.92 (16)
O3—S1—O1	112.90 (10)	C1—C6—H6A	120.0
O2—S1—O1	111.66 (10)	C5—C6—H6A	120.0
O3—S1—C1	106.32 (7)	C4—C7—H7A	109.5
O2—S1—C1	106.38 (7)	C4—C7—H7B	109.5
O1—S1—C1	106.03 (8)	H7A—C7—H7B	109.5
C10—N1—H1NC	109.7 (11)	C4—C7—H7C	109.5
C10—N1—H1NB	111.1 (11)	H7A—C7—H7C	109.5
H1NC—N1—H1NB	105.6 (14)	H7B—C7—H7C	109.5
C10—N1—H1NA	111.2 (12)	C9—C8—C13	121.74 (16)
H1NC—N1—H1NA	109.0 (13)	C9—C8—Cl1	118.62 (14)
H1NB—N1—H1NA	110.1 (13)	C13—C8—Cl1	119.64 (13)
C6—C1—C2	119.93 (14)	C10—C9—C8	117.81 (15)
C6—C1—S1	120.17 (12)	C10—C9—H9A	121.1
C2—C1—S1	119.91 (12)	C8—C9—H9A	121.1
C3—C2—C1	119.43 (16)	C9—C10—C11	121.86 (14)
C3—C2—H2A	120.3	C9—C10—N1	119.65 (14)
C1—C2—H2A	120.3	C11—C10—N1	118.47 (13)
C2—C3—C4	121.43 (16)	C12—C11—C10	118.70 (15)
C2—C3—H3A	119.3	C12—C11—H11A	120.7
C4—C3—H3A	119.3	C10—C11—H11A	120.7
C3—C4—C5	118.27 (16)	C13—C12—C11	120.97 (16)
C3—C4—C7	120.85 (19)	C13—C12—H12A	119.5
C5—C4—C7	120.9 (2)	C11—C12—H12A	119.5
C6—C5—C4	121.02 (17)	C12—C13—C8	118.91 (16)
C6—C5—H5A	119.5	C12—C13—H13A	120.5
C4—C5—H5A	119.5	C8—C13—H13A	120.5

O3—S1—C1—C6	−90.75 (15)	C2—C1—C6—C5	−0.2 (2)
O2—S1—C1—C6	148.65 (13)	S1—C1—C6—C5	−179.74 (13)
O1—S1—C1—C6	29.65 (16)	C4—C5—C6—C1	0.2 (3)
O3—S1—C1—C2	89.72 (14)	C13—C8—C9—C10	1.2 (2)
O2—S1—C1—C2	−30.89 (15)	Cl1—C8—C9—C10	−177.74 (11)
O1—S1—C1—C2	−149.88 (14)	C8—C9—C10—C11	−0.7 (2)
C6—C1—C2—C3	0.1 (2)	C8—C9—C10—N1	178.21 (13)
S1—C1—C2—C3	179.61 (12)	C9—C10—C11—C12	−0.4 (2)
C1—C2—C3—C4	0.1 (3)	N1—C10—C11—C12	−179.27 (15)
C2—C3—C4—C5	−0.1 (3)	C10—C11—C12—C13	1.0 (3)
C2—C3—C4—C7	−179.20 (16)	C11—C12—C13—C8	−0.6 (3)
C3—C4—C5—C6	−0.1 (3)	C9—C8—C13—C12	−0.5 (2)
C7—C4—C5—C6	179.06 (17)	Cl1—C8—C13—C12	178.34 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O1ⁱ	0.92 (1)	1.86 (1)	2.7640 (19)	168 (2)
N1—H1NC···O3ⁱⁱ	0.93 (1)	1.87 (1)	2.7806 (18)	166 (2)
N1—H1NB···O2	0.93 (1)	1.92 (1)	2.8282 (19)	167 (2)
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.76	3.267 (2)	115

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

Experimental details

Crystal data
Chemical formula	C₆H₇ClN⁺·C₇H₇O₃S⁻
M_r	299.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.7848 (3), 6.7767 (2), 16.1702 (4)
β (°)	105.081 (2)
V (Å³)	1352.71 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.32 × 0.26 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.872, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	10965, 3222, 2723
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.109, 1.02
No. of reflections	3222
No. of parameters	182
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.47

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O1ⁱ	0.916 (9)	1.861 (9)	2.7640 (19)	168.2 (18)
N1—H1NC···O3ⁱⁱ	0.928 (9)	1.871 (9)	2.7806 (18)	166.1 (16)
N1—H1NB···O2	0.927 (8)	1.919 (9)	2.8282 (19)	166.6 (15)
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.76	3.267 (2)	115

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

Acknowledgements

ASP and HSY thank the UoM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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Volume 67| Part 11| November 2011| Page o2925

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