catena-Poly[bis­[dimeth­yl(pyridine-κN)indium(III)]-μ4-benzene-1,3-diolato-bis­[di­methyl­indium(III)]-μ4-benzene-1,3-diolato]

Briand, G.G.; Decken, A.; Hoey, M.R.

doi:10.1107/S1600536813028985

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page m622

doi:10.1107/S1600536813028985

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catena-Poly[bis[dimethyl(pyridine-κN)indium(III)]-μ₄-benzene-1,3-diolato-bis[dimethylindium(III)]-μ₄-benzene-1,3-diolato]

Glen G. Briand,^a ^* Andreas Decken ^b and Marshall R. Hoey ^a

^aDepartment of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8, Canada, and ^bDepartment of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3, Canada
^*Correspondence e-mail: gbriand@mta.ca

(Received 9 October 2013; accepted 22 October 2013; online 26 October 2013)

The title compound, [In₂(CH₃)₄(C₆H₄O₂)(C₅H₅N)] or [{(CH₃)₂In}(1,3-O₂C₆H₄){In(CH₃)₂(py)}]_n, (py = pyridine) contains two crystallographically unique In^III ions which are in distorted tetrahedral C₂O₂ and distorted trigonal-bipyramidal C₂O₂N coordination environments. The In^III coordination centers are bridged head-to-head via In—O bonds, yielding four-membered In₂O₂ rings and zigzag polymeric chains along [001].

CCDC reference: 967698

Related literature

For background to dimethylindium aryloxides, see: Briand et al. (2010 ); Beachley et al. (2003 ); Hausslein et al. (1999 ); Blake et al. (2011 ); Bradley et al. (1988 ); Trentler et al. (1997 ). For dimethylindium compounds with bidentate imine-alkoxide ligands, see: Hu et al. (1999 ); Wu et al. (1999 ); Pal et al. (2013 ); Lewinski et al. (2003 ); Ghoshal et al. (2007 ).

Experimental

Crystal data

[In₂(CH₃)₄(C₆H₄O₂)(C₅H₅N)]
M_r = 476.97
Monoclinic, P 2₁ /n
a = 9.1584 (17) Å
b = 14.075 (3) Å
c = 13.856 (3) Å
β = 90.106 (3)°
V = 1786.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.58 mm⁻¹
T = 188 K
0.20 × 0.03 × 0.03 mm

Data collection

Bruker P4/SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.626, T_max = 0.938
12064 measured reflections
3967 independent reflections
2885 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 1.16
3967 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 2006 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b); molecular graphics: DIAMOND (Brandenburg, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Supporting information

CCDC reference: 967698

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813028985/lh5663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028985/lh5663Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028985/lh5663Isup3.cdx

checkCIF report

Comment top

Dimethylindium aryloxides [Me₂InOR]₂ form dimeric structures in the solid state via intermolecular In—O coordinate bonding interactions (Briand et al., 2010; Beachley et al., 2003; Hausslein et al., 1999; Blake et al., 2011; Bradley et al., 1988; Trentler et al., 1997). These structures feature distorted tetrahedral geometries at In, distorted trigonal planar or slightly pyramidal geometries at O, and symmetric near planar In₂O₂ ring cores. Substitution of monodentate alkoxide (–OR) ligands with bidentate imine-alkoxide ligands additionally results in an intramolecular In—N coordination, yielding distorted trigonal bipyramidal In centres and asymmetric In₂O₂ rings (Hu et al., 1999; Wu et al., 1999; Pal et al., 2013; Lewinski et al., 2003; Ghoshal et al., 2007). The molecular structure of (I) (Fig. 1) shows two crystallographically unique In atoms. In addition to the In1—O1 bond, In1 exhibits an intermolecular In1—O1ⁱ interaction. This results in a distorted tetrahedral C₂O₂ bonding environment for indium [C1—In1—C2 = 144.3 (3), O1—In1—O1ⁱ = 73.87 (14)°] and a symmetric In₂O₂ ring structure [In1—O1 = 2.172 (3), In1—O1ⁱ = 2.174 (3) Å]. Similarly, In2 is coordinated to two methyl C atoms [C3 and C4] and two aryloxide O atoms [O2 and O2ⁱⁱ], but is is also coordinated by the N atom of a pyridine molecule [2.486 (4) Å]. This results in a distorted trigonal bypyramidal C₂O₂N bonding environment for In, with the two methyl C atoms and a bridging O atom in equatorial positions [C3—In2—C4 = 142.5 (2), C3—In2—O2ⁱⁱ = 107.8 (2), C4—In2—O2ⁱⁱ = 109.25 (19)°], and the pyridine N atom and a bridging O atom in axial positions [O2—In2—N1 = 156.63 (13)°]. The axial In2—O2 bond distance [2.330 (3) Å] is longer than the equatorial In2—O2ⁱⁱ bond distance [2.152 (3) Å], presumably as a result of the trans influence of the pyridine N atom, resulting in an asymmetric In₂O₂ ring. The two unique In₂O₂ rings are bridged by the 1,3-benzenediolate phenyl ring, giving a zigzag polymeric structure along [001] (Fig. 2).

Related literature top

For background to dimethylindium aryloxides, see: Briand et al. (2010); Beachley et al. (2003); Hausslein et al. (1999); Blake et al. (2011); Bradley et al. (1988); Trentler et al. (1997). For dimethylindium compounds with bidentate imine-alkoxide ligands, see: Hu et al. (1999); Wu et al. (1999); Pal et al. (2013); Lewinski et al. (2003); Ghoshal et al. (2007).

Experimental top

Under an atmosphere of dinitrogen, InMe₃ (0.250 g, 1.56 mmol) was dissolved in diethyl ether (10 ml). Pyridine (0.125 g, 1.56 mmol) was added and the solution stirred for 30 min. Resorcinol (0.088 g, 0.78 mmol) was then added and the reaction mixture stirred for an additional 1 h. The reaction was then filtered and the filtrate allowed to sit at 296K. After 1 d, the solution was filtered to yield colourless crystals of [Me₂In(1,3-O₂C₆H₄)InMe₂(py)]_∞ (0.122 g, 0.256 mmol, 33%). Anal. Calc. for C₁₅H₂₁In₂NO₂: C, 37.77; H, 4.44; N, 2.94. Found: C, 38.32; H, 4.47; N, 2.88. F T—IR (ATR, cm^-1): 618 w, 698 s, 748 m, 772 w, 829 w, 844 w, 968 s, 1003 w, 1034 w, 1142 s, 1171 s, 1213 w, 1249 m, 1299 m, 1427 w, 1441 w, 1482 m, 1467 m, 1573 s, 2283 w, 2475 w, 2881 m, 3004 m. FT-Raman (cm^-1): 487 vs [ν_sym (Me—In—Me)], 524 w [ν_asym (Me—In—Me)], 994 m, 1034 m, 1159 m, 1305 w, 1586 w, 2920 m, 2982 w, 3064 m.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. Symmetry transformations used to generate equivalent atoms: (i) -x, 1 - y, 1 - z; (ii) -x, 1 - y, 2 - z.
	Fig. 2. Part of the crystal structure of (I) showing the zigzag polymeric structure along [001], with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. Symmetry transformations used to generate equivalent atoms: (i) -x, 1 - y, 1 - z; (ii) -x, 1 - y, 2 - z.

catena-Poly[bis[dimethyl(pyridine-κN)indium(III)]-µ₄-benzene-1,3-diolato-bis[dimethylindium(III)]-µ₄-benzene-1,3-diolato] top

Crystal data top

[In₂(CH₃)₄(C₆H₄O₂)(C₅H₅N)]	F(000) = 928
M_r = 476.97	D_x = 1.774 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5671 reflections
a = 9.1584 (17) Å	θ = 2.7–27.9°
b = 14.075 (3) Å	µ = 2.58 mm⁻¹
c = 13.856 (3) Å	T = 188 K
β = 90.106 (3)°	Rod, colourless
V = 1786.1 (6) Å³	0.20 × 0.03 × 0.03 mm
Z = 4

Data collection top

Bruker P4/SMART 1000 diffractometer	3967 independent reflections
Radiation source: fine-focus sealed tube, K760	2885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→11
T_min = 0.626, T_max = 0.938	k = −18→18
12064 measured reflections	l = −16→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0339P)² + 1.2232P] where P = (F_o² + 2F_c²)/3
3967 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[In₂(CH₃)₄(C₆H₄O₂)(C₅H₅N)]	V = 1786.1 (6) Å³
M_r = 476.97	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1584 (17) Å	µ = 2.58 mm⁻¹
b = 14.075 (3) Å	T = 188 K
c = 13.856 (3) Å	0.20 × 0.03 × 0.03 mm
β = 90.106 (3)°

Data collection top

Bruker P4/SMART 1000 diffractometer	3967 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	2885 reflections with I > 2σ(I)
T_min = 0.626, T_max = 0.938	R_int = 0.039
12064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.16	Δρ_max = 1.02 e Å⁻³
3967 reflections	Δρ_min = −0.72 e Å⁻³
185 parameters

Special details top

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

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. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
In1	0.12136 (4)	0.57110 (3)	0.43640 (3)	0.03464 (12)
In2	0.11428 (4)	0.39665 (3)	1.01934 (3)	0.02955 (11)
O1	0.0623 (4)	0.5253 (3)	0.5809 (2)	0.0361 (8)
O2	0.0754 (3)	0.5316 (2)	0.9254 (2)	0.0300 (8)
N1	0.0635 (5)	0.2789 (3)	1.1488 (3)	0.0396 (11)
C1	0.0184 (8)	0.7054 (5)	0.4259 (6)	0.073 (2)
H1A	0.0580	0.7480	0.4755	0.109*
H1B	−0.0870	0.6980	0.4356	0.109*
H1C	0.0365	0.7325	0.3619	0.109*
C2	0.3108 (7)	0.4920 (5)	0.3979 (5)	0.0631 (19)
H2A	0.3153	0.4856	0.3276	0.095*
H2B	0.3060	0.4288	0.4275	0.095*
H2C	0.3981	0.5253	0.4211	0.095*
C3	0.0431 (7)	0.3018 (4)	0.9068 (4)	0.0562 (17)
H3A	0.1234	0.2910	0.8616	0.084*
H3B	−0.0397	0.3302	0.8724	0.084*
H3C	0.0130	0.2412	0.9353	0.084*
C4	0.3053 (6)	0.4553 (4)	1.0846 (4)	0.0454 (15)
H4A	0.3067	0.5242	1.0746	0.068*
H4B	0.3923	0.4269	1.0553	0.068*
H4C	0.3047	0.4417	1.1540	0.068*
C5	0.1383 (5)	0.5416 (3)	0.6650 (3)	0.0270 (10)
C6	0.0693 (5)	0.5259 (3)	0.7530 (3)	0.0277 (11)
H6	−0.0282	0.5029	0.7544	0.033*
C7	0.1435 (5)	0.5439 (3)	0.8395 (3)	0.0264 (10)
C8	0.2872 (5)	0.5754 (4)	0.8361 (4)	0.0314 (11)
H8	0.3395	0.5870	0.8941	0.038*
C9	0.3536 (6)	0.5897 (4)	0.7479 (4)	0.0371 (13)
H9	0.4518	0.6115	0.7462	0.044*
C10	0.2808 (5)	0.5731 (3)	0.6622 (3)	0.0311 (11)
H10	0.3282	0.5832	0.6022	0.037*
C11	−0.0627 (6)	0.2311 (4)	1.1471 (5)	0.0464 (14)
H11	−0.1250	0.2380	1.0927	0.056*
C12	−0.1062 (7)	0.1719 (4)	1.2216 (5)	0.0572 (17)
H12	−0.1960	0.1383	1.2176	0.069*
C13	−0.0192 (8)	0.1624 (5)	1.3002 (5)	0.066 (2)
H13	−0.0476	0.1223	1.3520	0.080*
C14	0.1099 (8)	0.2112 (5)	1.3044 (5)	0.0614 (18)
H14	0.1723	0.2061	1.3590	0.074*
C15	0.1467 (7)	0.2677 (4)	1.2274 (4)	0.0479 (15)
H15	0.2369	0.3010	1.2302	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.0337 (2)	0.0504 (2)	0.0198 (2)	−0.00910 (16)	0.00038 (15)	0.00502 (16)
In2	0.0284 (2)	0.0370 (2)	0.02328 (19)	0.00222 (15)	0.00004 (14)	−0.00206 (15)
O1	0.035 (2)	0.058 (2)	0.0152 (17)	−0.0138 (17)	−0.0001 (15)	0.0008 (16)
O2	0.0281 (18)	0.047 (2)	0.0149 (17)	0.0054 (15)	0.0021 (14)	0.0016 (15)
N1	0.039 (3)	0.040 (3)	0.040 (3)	0.001 (2)	0.004 (2)	0.003 (2)
C1	0.080 (5)	0.058 (4)	0.081 (5)	−0.005 (4)	−0.005 (4)	0.018 (4)
C2	0.043 (4)	0.103 (6)	0.044 (4)	−0.001 (4)	0.004 (3)	−0.014 (4)
C3	0.078 (5)	0.054 (4)	0.037 (3)	−0.002 (3)	0.002 (3)	−0.018 (3)
C4	0.034 (3)	0.051 (4)	0.051 (4)	−0.007 (3)	−0.011 (3)	0.011 (3)
C5	0.035 (3)	0.032 (3)	0.014 (2)	−0.001 (2)	−0.001 (2)	0.0007 (19)
C6	0.022 (2)	0.040 (3)	0.022 (3)	−0.004 (2)	−0.001 (2)	0.000 (2)
C7	0.031 (3)	0.030 (3)	0.019 (2)	0.006 (2)	0.001 (2)	0.001 (2)
C8	0.028 (3)	0.048 (3)	0.018 (2)	−0.003 (2)	−0.004 (2)	−0.001 (2)
C9	0.025 (3)	0.058 (4)	0.029 (3)	−0.007 (2)	−0.001 (2)	0.004 (2)
C10	0.031 (3)	0.046 (3)	0.016 (2)	−0.007 (2)	0.003 (2)	−0.001 (2)
C11	0.049 (4)	0.040 (3)	0.050 (4)	−0.003 (3)	−0.002 (3)	0.001 (3)
C12	0.049 (4)	0.047 (4)	0.076 (5)	−0.010 (3)	0.009 (4)	0.009 (3)
C13	0.065 (5)	0.065 (5)	0.069 (5)	0.001 (4)	0.013 (4)	0.024 (4)
C14	0.073 (5)	0.069 (5)	0.042 (4)	0.011 (4)	−0.004 (3)	0.020 (3)
C15	0.050 (4)	0.048 (4)	0.046 (4)	0.001 (3)	0.002 (3)	0.008 (3)

Geometric parameters (Å, º) top

In1—C1	2.118 (7)	C3—H3C	0.9800
In1—C2	2.130 (6)	C4—H4A	0.9800
In1—O1	2.172 (3)	C4—H4B	0.9800
In1—O1ⁱ	2.174 (3)	C4—H4C	0.9800
In2—C4	2.134 (5)	C5—C10	1.379 (7)
In2—O2ⁱⁱ	2.152 (3)	C5—C6	1.393 (6)
In2—C3	2.152 (5)	C6—C7	1.400 (6)
In2—O2	2.330 (3)	C6—H6	0.9500
In2—N1	2.486 (4)	C7—C8	1.390 (7)
O1—C5	1.376 (5)	C8—C9	1.380 (7)
O1—In1ⁱ	2.174 (3)	C8—H8	0.9500
O2—C7	1.355 (5)	C9—C10	1.381 (7)
O2—In2ⁱⁱ	2.152 (3)	C9—H9	0.9500
N1—C11	1.337 (7)	C10—H10	0.9500
N1—C15	1.338 (7)	C11—C12	1.385 (8)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.355 (9)
C1—H1C	0.9800	C12—H12	0.9500
C2—H2A	0.9800	C13—C14	1.368 (9)
C2—H2B	0.9800	C13—H13	0.9500
C2—H2C	0.9800	C14—C15	1.373 (8)
C3—H3A	0.9800	C14—H14	0.9500
C3—H3B	0.9800	C15—H15	0.9500

C1—In1—C2	144.3 (3)	H3A—C3—H3C	109.5
C1—In1—O1	102.5 (2)	H3B—C3—H3C	109.5
C2—In1—O1	106.3 (2)	In2—C4—H4A	109.5
C1—In1—O1ⁱ	101.9 (2)	In2—C4—H4B	109.5
C2—In1—O1ⁱ	106.1 (2)	H4A—C4—H4B	109.5
O1—In1—O1ⁱ	73.87 (14)	In2—C4—H4C	109.5
C4—In2—O2ⁱⁱ	109.25 (19)	H4A—C4—H4C	109.5
C4—In2—C3	142.5 (2)	H4B—C4—H4C	109.5
O2ⁱⁱ—In2—C3	107.8 (2)	O1—C5—C10	120.5 (4)
C4—In2—O2	92.62 (17)	O1—C5—C6	119.0 (4)
O2ⁱⁱ—In2—O2	72.15 (13)	C10—C5—C6	120.4 (4)
C3—In2—O2	93.2 (2)	C5—C6—C7	120.0 (4)
C4—In2—N1	96.11 (19)	C5—C6—H6	120.0
O2ⁱⁱ—In2—N1	84.49 (13)	C7—C6—H6	120.0
C3—In2—N1	93.0 (2)	O2—C7—C8	120.5 (4)
O2—In2—N1	156.63 (13)	O2—C7—C6	120.3 (4)
C5—O1—In1	127.2 (3)	C8—C7—C6	119.1 (4)
C5—O1—In1ⁱ	126.0 (3)	C9—C8—C7	119.8 (5)
In1—O1—In1ⁱ	106.13 (14)	C9—C8—H8	120.1
C7—O2—In2ⁱⁱ	128.7 (3)	C7—C8—H8	120.1
C7—O2—In2	121.6 (3)	C8—C9—C10	121.5 (5)
In2ⁱⁱ—O2—In2	107.85 (13)	C8—C9—H9	119.2
C11—N1—C15	116.4 (5)	C10—C9—H9	119.2
C11—N1—In2	119.1 (4)	C5—C10—C9	119.1 (4)
C15—N1—In2	124.0 (4)	C5—C10—H10	120.4
In1—C1—H1A	109.5	C9—C10—H10	120.4
In1—C1—H1B	109.5	N1—C11—C12	122.7 (6)
H1A—C1—H1B	109.5	N1—C11—H11	118.7
In1—C1—H1C	109.5	C12—C11—H11	118.7
H1A—C1—H1C	109.5	C13—C12—C11	119.2 (6)
H1B—C1—H1C	109.5	C13—C12—H12	120.4
In1—C2—H2A	109.5	C11—C12—H12	120.4
In1—C2—H2B	109.5	C12—C13—C14	119.5 (6)
H2A—C2—H2B	109.5	C12—C13—H13	120.3
In1—C2—H2C	109.5	C14—C13—H13	120.3
H2A—C2—H2C	109.5	C13—C14—C15	118.1 (7)
H2B—C2—H2C	109.5	C13—C14—H14	120.9
In2—C3—H3A	109.5	C15—C14—H14	120.9
In2—C3—H3B	109.5	N1—C15—C14	124.1 (6)
H3A—C3—H3B	109.5	N1—C15—H15	118.0
In2—C3—H3C	109.5	C14—C15—H15	118.0

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

Experimental details

Crystal data
Chemical formula	[In₂(CH₃)₄(C₆H₄O₂)(C₅H₅N)]
M_r	476.97
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	188
a, b, c (Å)	9.1584 (17), 14.075 (3), 13.856 (3)
β (°)	90.106 (3)
V (Å³)	1786.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.58
Crystal size (mm)	0.20 × 0.03 × 0.03

Data collection
Diffractometer	Bruker P4/SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.626, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	12064, 3967, 2885
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.087, 1.16
No. of reflections	3967
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.72

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008b), SHELXL2013 (Sheldrick, 2008b), DIAMOND (Brandenburg, 2012), SHELXTL (Sheldrick, 2008b).

Acknowledgements

This work was supported by the Natural Sciences and Engineering Research Council of Canada, the New Brunswick Innovation Foundation, the Canadian Foundation for Innovation and Mount Allison University.

References

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