supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, m183    [ doi:10.1107/S1600536807065828 ]

Bis(tetramethylammonium) tetrachloridozincate(II), phase VI

A. B. S. Curtiss, G. T. Musie and D. R. Powell

Abstract top

Phase VI of bis(tetramethylammonium) tetrachlorozincate(II), (C4H12N)2[ZnCl4], contains three formula units per asymmetric unit. Several short C-H...Cl contacts [2.70 (3) and 2.72 (4) Å] are observed, but they are believed to participate only in van der Waals interactions. The crystal studied exhibited inversion twinning.

Comment top

Bis(tetramethylammonium) tetrachlorozincate(II) undergoes five solid-solid phase transitions with decreasing temperature according to a calorimetric study by Ruiz-Larrea et al. (1981). The room temperature phase I crystallized in the space group Pnma with a = 12.276 (2), b = 8.998 (2), and c = 15.541 (2) Å (Wiesner et al., 1967). Weak incommensurate lattice spots in phases II, III, and IV have shown that these two phases are small distortions of the room temperature phase (Madariaga et al., 1987). Similarly, phase V was found to be an incommensurately modulated structure related to phase I (Zuñiga et al., 1989).

No evidence of superlattice spots were observed in the frame data for phase VI. Short C—H···Cl contacts were observed, but because of the very large estimated pKa of 42 for the protons of the cations (Zhang & Bordwell, 1994), it is unlikely that any of these contacts are weak hydrogen bonds. There were three formula units in the asymmetric unit of the cell (Fig. 1).

Related literature top

For related literature, see: Madariaga et al. (1987); Ruiz-Larrea et al. (1981); Wiesner et al. (1967); Zuñiga et al. (1989); Zhang & Bordwell (1994).

Experimental top

Single crystals of bis(tetramethylammonium) tetrachlorozincate(II) were grown by slow diffusion of diethyl ether into a methanol solution of ZnCl2 and N(CH3)4OH in a 1:3 mole ratio over the course of three days.

Refinement top

The methyl H atoms were initially located by geometry. The H atoms were then refined with distances of 0.98 Å and Uiso(H) = 1.5Ueq(C), but each methyl group was allowed to rotate freely about its N—C bond.

The refined Flack parameter indicated racemic twinning in the sample.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL (Sheldrick, 2000); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).

Figures top
[Figure 1] Fig. 1. View of the unique atoms showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
bis(tetramethylammonium) tetrachlorozincate(II) top
Crystal data top
(C4H12N)2[ZnCl4]F(000) = 2208
Mr = 355.46Dx = 1.442 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6850 reflections
a = 8.9114 (18) Åθ = 2.5–28.2°
b = 15.105 (3) ŵ = 2.13 mm−1
c = 36.493 (7) ÅT = 100 K
V = 4912.2 (17) Å3Plate, colourless
Z = 120.36 × 0.24 × 0.04 mm
Data collection top
Bruker APEX CCD
diffractometer		9616 independent reflections
Radiation source: fine-focus sealed tube9039 reflections with I > 2σ(I)
graphiteRint = 0.038
\ scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		h = −10→10
Tmin = 0.512, Tmax = 0.918k = −18→18
32538 measured reflectionsl = −44→45
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.055 w = 1/[σ2(Fo2) + (0.022P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
9616 reflectionsΔρmax = 0.43 e Å−3
407 parametersΔρmin = −0.29 e Å−3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.611 (6)
Crystal data top
(C4H12N)2[ZnCl4]V = 4912.2 (17) Å3
Mr = 355.46Z = 12
Orthorhombic, P212121Mo Kα radiation
a = 8.9114 (18) ŵ = 2.13 mm−1
b = 15.105 (3) ÅT = 100 K
c = 36.493 (7) Å0.36 × 0.24 × 0.04 mm
Data collection top
Bruker APEX CCD
diffractometer		9616 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		9039 reflections with I > 2σ(I)
Tmin = 0.512, Tmax = 0.918Rint = 0.038
32538 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.055Δρmax = 0.43 e Å−3
S = 1.00Δρmin = −0.29 e Å−3
9616 reflectionsAbsolute structure: Flack (1983)
407 parametersFlack parameter: 0.611 (6)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn1A0.22269 (3)0.833130 (18)0.249954 (7)0.01451 (7)
Cl1A0.27151 (7)0.83942 (4)0.311249 (16)0.01927 (14)
Cl2A0.42172 (7)0.89470 (4)0.220415 (17)0.02094 (15)
Cl3A0.01026 (7)0.91090 (4)0.236224 (17)0.02043 (14)
Cl4A0.18901 (8)0.69109 (4)0.231878 (17)0.02295 (15)
Zn1B0.80374 (3)0.648812 (18)0.085633 (7)0.01432 (7)
Cl1B0.78781 (7)0.67180 (4)0.024348 (16)0.01814 (13)
Cl2B0.99810 (7)0.55514 (4)0.098555 (17)0.01982 (15)
Cl3B0.58278 (8)0.59089 (4)0.106043 (18)0.02098 (15)
Cl4B0.84775 (8)0.77752 (4)0.115946 (17)0.01842 (14)
Zn1C0.27960 (3)0.148178 (18)0.084326 (7)0.01390 (7)
Cl1C0.30736 (7)0.14537 (4)0.145927 (16)0.01915 (14)
Cl2C0.32460 (8)0.28462 (4)0.060498 (18)0.02114 (15)
Cl3C0.44003 (8)0.04975 (4)0.057901 (18)0.02362 (16)
Cl4C0.04001 (7)0.10798 (4)0.069889 (17)0.02188 (15)
N1D0.7769 (2)0.34272 (13)0.04975 (5)0.0161 (5)
C1D0.7608 (3)0.34836 (17)0.09057 (6)0.0214 (6)
H1D10.65610.33740.09740.032*
H1D20.79060.40750.09890.032*
H1D30.82530.30390.10210.032*
C2D0.7222 (3)0.25421 (16)0.03673 (7)0.0222 (6)
H2D10.72740.25180.00990.033*
H2D20.61810.24550.04460.033*
H2D30.78540.20740.04710.033*
C3D0.6849 (3)0.41380 (17)0.03245 (7)0.0268 (7)
H3D10.69540.41060.00580.040*
H3D20.71970.47170.04110.040*
H3D30.57930.40580.03910.040*
C4D0.9376 (3)0.35435 (19)0.03958 (7)0.0248 (6)
H4D10.99670.30530.04960.037*
H4D20.97470.41040.04960.037*
H4D30.94730.35500.01280.037*
N1E0.2499 (2)0.40749 (14)0.17102 (5)0.0148 (5)
C1E0.1088 (3)0.36434 (17)0.15805 (8)0.0252 (7)
H1E10.06750.39790.13740.038*
H1E20.03550.36310.17810.038*
H1E30.13060.30370.15020.038*
C2E0.3602 (3)0.41315 (18)0.14052 (7)0.0278 (7)
H2E10.31720.44770.12040.042*
H2E20.38420.35340.13180.042*
H2E30.45200.44200.14930.042*
C3E0.2129 (3)0.49855 (16)0.18458 (7)0.0218 (6)
H3E10.30470.52770.19310.033*
H3E20.14120.49430.20490.033*
H3E30.16850.53320.16460.033*
C4E0.3153 (3)0.35468 (17)0.20164 (7)0.0233 (6)
H4E10.34320.29580.19260.035*
H4E20.24100.34870.22130.035*
H4E30.40460.38480.21110.035*
N1F0.2919 (3)0.82358 (13)0.11507 (5)0.0179 (5)
C1F0.2556 (3)0.74168 (17)0.13618 (8)0.0279 (7)
H1F10.28000.75080.16210.042*
H1F20.31460.69210.12660.042*
H1F30.14850.72840.13370.042*
C2F0.4559 (3)0.84202 (19)0.11789 (8)0.0283 (7)
H2F10.48000.89570.10400.042*
H2F20.51240.79190.10790.042*
H2F30.48310.85060.14370.042*
C3F0.2049 (3)0.89951 (17)0.13031 (8)0.0284 (7)
H3F10.09730.88640.12880.043*
H3F20.22690.95300.11610.043*
H3F30.23320.90890.15600.043*
C4F0.2506 (3)0.8116 (2)0.07569 (7)0.0379 (8)
H4F10.27410.86580.06210.057*
H4F20.14290.79920.07380.057*
H4F30.30750.76200.06540.057*
N1G0.7277 (2)0.63485 (14)0.21747 (5)0.0161 (5)
C1G0.5783 (3)0.5939 (2)0.21077 (8)0.0304 (7)
H1G10.50170.62580.22480.046*
H1G20.58050.53180.21850.046*
H1G30.55440.59730.18460.046*
C2G0.7243 (4)0.73057 (17)0.20696 (7)0.0286 (7)
H2G10.82190.75760.21220.043*
H2G20.64610.76100.22100.043*
H2G30.70260.73590.18070.043*
C3G0.8431 (3)0.58795 (18)0.19485 (7)0.0244 (7)
H3G10.81740.59350.16880.037*
H3G20.84560.52520.20170.037*
H3G30.94190.61450.19920.037*
C4G0.7650 (3)0.62664 (18)0.25733 (7)0.0249 (7)
H4G10.68860.65740.27190.037*
H4G20.86340.65320.26200.037*
H4G30.76730.56390.26420.037*
N1H0.2840 (2)0.56575 (13)−0.00491 (5)0.0147 (5)
C1H0.2778 (3)0.46942 (16)0.00445 (7)0.0219 (6)
H1H10.27240.46240.03110.033*
H1H20.36820.4400−0.00480.033*
H1H30.18890.4428−0.00680.033*
C2H0.1461 (3)0.61057 (18)0.00861 (8)0.0264 (7)
H2H10.05790.5847−0.00330.040*
H2H20.15150.67390.00290.040*
H2H30.13810.60270.03520.040*
C3H0.2935 (3)0.57694 (17)−0.04539 (6)0.0230 (6)
H3H10.38350.5470−0.05460.035*
H3H20.29880.6401−0.05130.035*
H3H30.20430.5510−0.05690.035*
C4H0.4208 (3)0.60584 (18)0.01198 (8)0.0301 (7)
H4H10.51050.57670.00220.045*
H4H20.41720.59800.03860.045*
H4H30.42440.66920.00620.045*
N1I0.7744 (2)1.07188 (13)0.16264 (5)0.0150 (5)
C1I0.9184 (3)1.11122 (17)0.17517 (7)0.0216 (6)
H1I10.96151.07440.19460.032*
H1I20.90021.17100.18460.032*
H1I30.98861.11430.15450.032*
C2I0.6673 (3)1.06734 (18)0.19391 (7)0.0260 (7)
H2I10.70821.02850.21300.039*
H2I20.57111.04370.18540.039*
H2I30.65231.12680.20400.039*
C3I0.8031 (4)0.98137 (16)0.14806 (7)0.0286 (7)
H3I10.87140.98510.12710.043*
H3I20.70810.95470.14030.043*
H3I30.84870.94480.16720.043*
C4I0.7082 (3)1.12811 (17)0.13312 (7)0.0233 (6)
H4I10.77881.13230.11260.035*
H4I20.68801.18750.14280.035*
H4I30.61421.10140.12460.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn1A0.01419 (16)0.01415 (15)0.01521 (15)0.00001 (13)0.00065 (12)0.00035 (12)
Cl1A0.0185 (3)0.0239 (3)0.0154 (3)−0.0007 (3)−0.0014 (3)0.0007 (3)
Cl2A0.0165 (3)0.0255 (4)0.0209 (3)−0.0037 (3)0.0028 (3)0.0024 (3)
Cl3A0.0162 (3)0.0223 (3)0.0227 (3)0.0038 (3)−0.0018 (3)0.0021 (3)
Cl4A0.0318 (4)0.0155 (3)0.0215 (3)−0.0028 (3)−0.0004 (3)−0.0019 (3)
Zn1B0.01474 (15)0.01379 (14)0.01444 (14)−0.00018 (13)0.00038 (13)0.00079 (12)
Cl1B0.0189 (3)0.0207 (3)0.0149 (3)0.0009 (3)−0.0001 (3)0.0016 (3)
Cl2B0.0205 (4)0.0189 (3)0.0201 (3)0.0046 (3)−0.0015 (3)0.0023 (3)
Cl3B0.0177 (4)0.0240 (3)0.0212 (3)−0.0048 (3)0.0029 (3)0.0013 (3)
Cl4B0.0204 (4)0.0157 (3)0.0192 (3)−0.0012 (3)−0.0008 (3)−0.0020 (3)
Zn1C0.01250 (15)0.01516 (14)0.01404 (14)0.00037 (13)0.00063 (13)−0.00004 (12)
Cl1C0.0193 (3)0.0243 (3)0.0138 (3)0.0011 (3)−0.0003 (3)−0.0010 (3)
Cl2C0.0212 (4)0.0187 (3)0.0235 (3)−0.0020 (3)−0.0005 (3)0.0038 (3)
Cl3C0.0237 (4)0.0247 (4)0.0225 (3)0.0072 (3)0.0054 (3)−0.0017 (3)
Cl4C0.0145 (4)0.0288 (4)0.0224 (3)−0.0039 (3)−0.0024 (3)−0.0007 (3)
N1D0.0156 (11)0.0178 (11)0.0150 (11)−0.0001 (10)0.0002 (9)−0.0003 (9)
C1D0.0268 (16)0.0229 (14)0.0146 (13)−0.0023 (12)0.0036 (11)−0.0007 (11)
C2D0.0252 (16)0.0192 (14)0.0221 (15)−0.0005 (13)−0.0004 (13)−0.0040 (11)
C3D0.0293 (19)0.0248 (15)0.0262 (16)0.0108 (14)−0.0038 (14)0.0033 (12)
C4D0.0153 (15)0.0317 (16)0.0274 (15)−0.0029 (13)0.0060 (12)0.0017 (13)
N1E0.0126 (13)0.0169 (11)0.0150 (11)0.0003 (9)0.0010 (9)−0.0013 (9)
C1E0.0142 (15)0.0238 (15)0.0377 (17)−0.0041 (12)−0.0099 (13)0.0033 (13)
C2E0.0288 (18)0.0265 (16)0.0280 (16)−0.0022 (14)0.0104 (14)−0.0014 (13)
C3E0.0208 (16)0.0181 (14)0.0265 (15)0.0017 (13)−0.0006 (13)−0.0041 (12)
C4E0.0224 (16)0.0277 (15)0.0200 (14)0.0081 (14)−0.0014 (12)0.0011 (12)
N1F0.0177 (12)0.0198 (11)0.0163 (11)−0.0004 (11)−0.0012 (10)−0.0019 (9)
C1F0.0236 (17)0.0210 (15)0.0392 (18)0.0014 (12)0.0038 (14)0.0097 (13)
C2F0.0157 (15)0.0356 (17)0.0336 (16)−0.0034 (14)−0.0017 (12)0.0066 (14)
C3F0.0269 (17)0.0231 (15)0.0352 (17)0.0040 (14)−0.0053 (15)−0.0052 (13)
C4F0.035 (2)0.060 (2)0.0189 (16)−0.0039 (16)−0.0039 (13)−0.0064 (15)
N1G0.0156 (12)0.0180 (11)0.0146 (11)0.0013 (10)−0.0001 (9)0.0000 (9)
C1G0.0191 (16)0.0458 (19)0.0265 (16)−0.0087 (15)−0.0016 (13)0.0008 (14)
C2G0.044 (2)0.0162 (14)0.0253 (16)0.0071 (14)0.0024 (15)0.0030 (12)
C3G0.0211 (16)0.0253 (15)0.0269 (16)0.0051 (13)0.0043 (13)−0.0059 (13)
C4G0.0328 (18)0.0256 (15)0.0164 (14)−0.0001 (13)−0.0070 (12)0.0015 (12)
N1H0.0152 (12)0.0142 (10)0.0148 (11)−0.0031 (10)−0.0011 (10)0.0020 (9)
C1H0.0238 (16)0.0156 (13)0.0263 (15)0.0000 (13)0.0017 (13)0.0049 (11)
C2H0.0246 (17)0.0232 (15)0.0313 (16)0.0063 (13)0.0131 (13)−0.0006 (13)
C3H0.0274 (17)0.0254 (15)0.0163 (13)−0.0005 (14)0.0027 (13)0.0053 (11)
C4H0.0286 (18)0.0240 (16)0.0377 (18)−0.0052 (14)−0.0139 (14)0.0024 (14)
N1I0.0118 (11)0.0180 (11)0.0153 (11)−0.0013 (9)−0.0015 (9)−0.0001 (9)
C1I0.0171 (15)0.0231 (15)0.0246 (15)−0.0039 (13)−0.0024 (12)−0.0027 (12)
C2I0.0228 (17)0.0345 (17)0.0207 (15)−0.0058 (14)0.0032 (13)0.0023 (13)
C3I0.0325 (19)0.0198 (14)0.0336 (17)0.0005 (14)−0.0048 (15)−0.0094 (13)
C4I0.0198 (15)0.0262 (15)0.0238 (14)0.0029 (13)−0.0002 (13)0.0043 (12)
Geometric parameters (Å, °) top
Zn1A—Cl4A2.2645 (8)C3F—H3F10.9800
Zn1A—Cl2A2.2743 (8)C3F—H3F20.9800
Zn1A—Cl1A2.2807 (8)C3F—H3F30.9800
Zn1A—Cl3A2.2836 (8)C4F—H4F10.9800
Zn1B—Cl1B2.2677 (8)C4F—H4F20.9800
Zn1B—Cl4B2.2709 (7)C4F—H4F30.9800
Zn1B—Cl3B2.2797 (8)N1G—C1G1.488 (3)
Zn1B—Cl2B2.2857 (8)N1G—C2G1.496 (3)
Zn1C—Cl1C2.2620 (8)N1G—C3G1.497 (3)
Zn1C—Cl2C2.2726 (8)N1G—C4G1.497 (3)
Zn1C—Cl3C2.2770 (8)C1G—H1G10.9800
Zn1C—Cl4C2.2814 (8)C1G—H1G20.9800
N1D—C4D1.490 (3)C1G—H1G30.9800
N1D—C3D1.491 (3)C2G—H2G10.9800
N1D—C1D1.499 (3)C2G—H2G20.9800
N1D—C2D1.500 (3)C2G—H2G30.9800
C1D—H1D10.9800C3G—H3G10.9800
C1D—H1D20.9800C3G—H3G20.9800
C1D—H1D30.9800C3G—H3G30.9800
C2D—H2D10.9800C4G—H4G10.9800
C2D—H2D20.9800C4G—H4G20.9800
C2D—H2D30.9800C4G—H4G30.9800
C3D—H3D10.9800N1H—C2H1.487 (3)
C3D—H3D20.9800N1H—C3H1.489 (3)
C3D—H3D30.9800N1H—C4H1.494 (3)
C4D—H4D10.9800N1H—C1H1.496 (3)
C4D—H4D20.9800C1H—H1H10.9800
C4D—H4D30.9800C1H—H1H20.9800
N1E—C2E1.488 (3)C1H—H1H30.9800
N1E—C4E1.491 (3)C2H—H2H10.9800
N1E—C1E1.494 (3)C2H—H2H20.9800
N1E—C3E1.498 (3)C2H—H2H30.9800
C1E—H1E10.9800C3H—H3H10.9800
C1E—H1E20.9800C3H—H3H20.9800
C1E—H1E30.9800C3H—H3H30.9800
C2E—H2E10.9800C4H—H4H10.9800
C2E—H2E20.9800C4H—H4H20.9800
C2E—H2E30.9800C4H—H4H30.9800
C3E—H3E10.9800N1I—C1I1.486 (3)
C3E—H3E20.9800N1I—C3I1.489 (3)
C3E—H3E30.9800N1I—C2I1.490 (3)
C4E—H4E10.9800N1I—C4I1.493 (3)
C4E—H4E20.9800C1I—H1I10.9800
C4E—H4E30.9800C1I—H1I20.9800
N1F—C2F1.491 (3)C1I—H1I30.9800
N1F—C3F1.492 (3)C2I—H2I10.9800
N1F—C1F1.493 (3)C2I—H2I20.9800
N1F—C4F1.494 (3)C2I—H2I30.9800
C1F—H1F10.9800C3I—H3I10.9800
C1F—H1F20.9800C3I—H3I20.9800
C1F—H1F30.9800C3I—H3I30.9800
C2F—H2F10.9800C4I—H4I10.9800
C2F—H2F20.9800C4I—H4I20.9800
C2F—H2F30.9800C4I—H4I30.9800
Cl4A—Zn1A—Cl2A110.65 (3)N1F—C3F—H3F3109.5
Cl4A—Zn1A—Cl1A110.51 (3)H3F1—C3F—H3F3109.5
Cl2A—Zn1A—Cl1A107.40 (3)H3F2—C3F—H3F3109.5
Cl4A—Zn1A—Cl3A108.27 (3)N1F—C4F—H4F1109.5
Cl2A—Zn1A—Cl3A109.40 (3)N1F—C4F—H4F2109.5
Cl1A—Zn1A—Cl3A110.60 (3)H4F1—C4F—H4F2109.5
Cl1B—Zn1B—Cl4B111.11 (3)N1F—C4F—H4F3109.5
Cl1B—Zn1B—Cl3B109.08 (3)H4F1—C4F—H4F3109.5
Cl4B—Zn1B—Cl3B108.58 (3)H4F2—C4F—H4F3109.5
Cl1B—Zn1B—Cl2B110.23 (3)C1G—N1G—C2G109.9 (2)
Cl4B—Zn1B—Cl2B107.37 (3)C1G—N1G—C3G109.1 (2)
Cl3B—Zn1B—Cl2B110.46 (3)C2G—N1G—C3G109.3 (2)
Cl1C—Zn1C—Cl2C112.21 (3)C1G—N1G—C4G108.9 (2)
Cl1C—Zn1C—Cl3C109.88 (3)C2G—N1G—C4G109.50 (19)
Cl2C—Zn1C—Cl3C108.62 (3)C3G—N1G—C4G110.1 (2)
Cl1C—Zn1C—Cl4C109.08 (3)N1G—C1G—H1G1109.5
Cl2C—Zn1C—Cl4C108.55 (3)N1G—C1G—H1G2109.5
Cl3C—Zn1C—Cl4C108.42 (3)H1G1—C1G—H1G2109.5
C4D—N1D—C3D109.7 (2)N1G—C1G—H1G3109.5
C4D—N1D—C1D109.4 (2)H1G1—C1G—H1G3109.5
C3D—N1D—C1D109.11 (19)H1G2—C1G—H1G3109.5
C4D—N1D—C2D109.8 (2)N1G—C2G—H2G1109.5
C3D—N1D—C2D109.2 (2)N1G—C2G—H2G2109.5
C1D—N1D—C2D109.54 (19)H2G1—C2G—H2G2109.5
N1D—C1D—H1D1109.5N1G—C2G—H2G3109.5
N1D—C1D—H1D2109.5H2G1—C2G—H2G3109.5
H1D1—C1D—H1D2109.5H2G2—C2G—H2G3109.5
N1D—C1D—H1D3109.5N1G—C3G—H3G1109.5
H1D1—C1D—H1D3109.5N1G—C3G—H3G2109.5
H1D2—C1D—H1D3109.5H3G1—C3G—H3G2109.5
N1D—C2D—H2D1109.5N1G—C3G—H3G3109.5
N1D—C2D—H2D2109.5H3G1—C3G—H3G3109.5
H2D1—C2D—H2D2109.5H3G2—C3G—H3G3109.5
N1D—C2D—H2D3109.5N1G—C4G—H4G1109.5
H2D1—C2D—H2D3109.5N1G—C4G—H4G2109.5
H2D2—C2D—H2D3109.5H4G1—C4G—H4G2109.5
N1D—C3D—H3D1109.5N1G—C4G—H4G3109.5
N1D—C3D—H3D2109.5H4G1—C4G—H4G3109.5
H3D1—C3D—H3D2109.5H4G2—C4G—H4G3109.5
N1D—C3D—H3D3109.5C2H—N1H—C3H108.9 (2)
H3D1—C3D—H3D3109.5C2H—N1H—C4H110.7 (2)
H3D2—C3D—H3D3109.5C3H—N1H—C4H108.5 (2)
N1D—C4D—H4D1109.5C2H—N1H—C1H109.7 (2)
N1D—C4D—H4D2109.5C3H—N1H—C1H109.81 (19)
H4D1—C4D—H4D2109.5C4H—N1H—C1H109.3 (2)
N1D—C4D—H4D3109.5N1H—C1H—H1H1109.5
H4D1—C4D—H4D3109.5N1H—C1H—H1H2109.5
H4D2—C4D—H4D3109.5H1H1—C1H—H1H2109.5
C2E—N1E—C4E109.5 (2)N1H—C1H—H1H3109.5
C2E—N1E—C1E110.2 (2)H1H1—C1H—H1H3109.5
C4E—N1E—C1E109.4 (2)H1H2—C1H—H1H3109.5
C2E—N1E—C3E109.9 (2)N1H—C2H—H2H1109.5
C4E—N1E—C3E109.25 (19)N1H—C2H—H2H2109.5
C1E—N1E—C3E108.6 (2)H2H1—C2H—H2H2109.5
N1E—C1E—H1E1109.5N1H—C2H—H2H3109.5
N1E—C1E—H1E2109.5H2H1—C2H—H2H3109.5
H1E1—C1E—H1E2109.5H2H2—C2H—H2H3109.5
N1E—C1E—H1E3109.5N1H—C3H—H3H1109.5
H1E1—C1E—H1E3109.5N1H—C3H—H3H2109.5
H1E2—C1E—H1E3109.5H3H1—C3H—H3H2109.5
N1E—C2E—H2E1109.5N1H—C3H—H3H3109.5
N1E—C2E—H2E2109.5H3H1—C3H—H3H3109.5
H2E1—C2E—H2E2109.5H3H2—C3H—H3H3109.5
N1E—C2E—H2E3109.5N1H—C4H—H4H1109.5
H2E1—C2E—H2E3109.5N1H—C4H—H4H2109.5
H2E2—C2E—H2E3109.5H4H1—C4H—H4H2109.5
N1E—C3E—H3E1109.5N1H—C4H—H4H3109.5
N1E—C3E—H3E2109.5H4H1—C4H—H4H3109.5
H3E1—C3E—H3E2109.5H4H2—C4H—H4H3109.5
N1E—C3E—H3E3109.5C1I—N1I—C3I109.2 (2)
H3E1—C3E—H3E3109.5C1I—N1I—C2I109.63 (19)
H3E2—C3E—H3E3109.5C3I—N1I—C2I110.0 (2)
N1E—C4E—H4E1109.5C1I—N1I—C4I109.6 (2)
N1E—C4E—H4E2109.5C3I—N1I—C4I109.4 (2)
H4E1—C4E—H4E2109.5C2I—N1I—C4I109.0 (2)
N1E—C4E—H4E3109.5N1I—C1I—H1I1109.5
H4E1—C4E—H4E3109.5N1I—C1I—H1I2109.5
H4E2—C4E—H4E3109.5H1I1—C1I—H1I2109.5
C2F—N1F—C3F109.9 (2)N1I—C1I—H1I3109.5
C2F—N1F—C1F109.4 (2)H1I1—C1I—H1I3109.5
C3F—N1F—C1F109.4 (2)H1I2—C1I—H1I3109.5
C2F—N1F—C4F109.3 (2)N1I—C2I—H2I1109.5
C3F—N1F—C4F108.9 (2)N1I—C2I—H2I2109.5
C1F—N1F—C4F110.0 (2)H2I1—C2I—H2I2109.5
N1F—C1F—H1F1109.5N1I—C2I—H2I3109.5
N1F—C1F—H1F2109.5H2I1—C2I—H2I3109.5
H1F1—C1F—H1F2109.5H2I2—C2I—H2I3109.5
N1F—C1F—H1F3109.5N1I—C3I—H3I1109.5
H1F1—C1F—H1F3109.5N1I—C3I—H3I2109.5
H1F2—C1F—H1F3109.5H3I1—C3I—H3I2109.5
N1F—C2F—H2F1109.5N1I—C3I—H3I3109.5
N1F—C2F—H2F2109.5H3I1—C3I—H3I3109.5
H2F1—C2F—H2F2109.5H3I2—C3I—H3I3109.5
N1F—C2F—H2F3109.5N1I—C4I—H4I1109.5
H2F1—C2F—H2F3109.5N1I—C4I—H4I2109.5
H2F2—C2F—H2F3109.5H4I1—C4I—H4I2109.5
N1F—C3F—H3F1109.5N1I—C4I—H4I3109.5
N1F—C3F—H3F2109.5H4I1—C4I—H4I3109.5
H3F1—C3F—H3F2109.5H4I2—C4I—H4I3109.5
Table 1
Selected geometric parameters (Å, °) top
Zn1A—Cl4A2.2645 (8)N1E—C1E1.494 (3)
Zn1A—Cl2A2.2743 (8)N1E—C3E1.498 (3)
Zn1A—Cl1A2.2807 (8)N1F—C2F1.491 (3)
Zn1A—Cl3A2.2836 (8)N1F—C3F1.492 (3)
Zn1B—Cl1B2.2677 (8)N1F—C1F1.493 (3)
Zn1B—Cl4B2.2709 (7)N1F—C4F1.494 (3)
Zn1B—Cl3B2.2797 (8)N1G—C1G1.488 (3)
Zn1B—Cl2B2.2857 (8)N1G—C2G1.496 (3)
Zn1C—Cl1C2.2620 (8)N1G—C3G1.497 (3)
Zn1C—Cl2C2.2726 (8)N1G—C4G1.497 (3)
Zn1C—Cl3C2.2770 (8)N1H—C2H1.487 (3)
Zn1C—Cl4C2.2814 (8)N1H—C3H1.489 (3)
N1D—C4D1.490 (3)N1H—C4H1.494 (3)
N1D—C3D1.491 (3)N1H—C1H1.496 (3)
N1D—C1D1.499 (3)N1I—C1I1.486 (3)
N1D—C2D1.500 (3)N1I—C3I1.489 (3)
N1E—C2E1.488 (3)N1I—C2I1.490 (3)
N1E—C4E1.491 (3)N1I—C4I1.493 (3)
Cl4A—Zn1A—Cl2A110.65 (3)C2E—N1E—C3E109.9 (2)
Cl4A—Zn1A—Cl1A110.51 (3)C4E—N1E—C3E109.25 (19)
Cl2A—Zn1A—Cl1A107.40 (3)C1E—N1E—C3E108.6 (2)
Cl4A—Zn1A—Cl3A108.27 (3)C2F—N1F—C3F109.9 (2)
Cl2A—Zn1A—Cl3A109.40 (3)C2F—N1F—C1F109.4 (2)
Cl1A—Zn1A—Cl3A110.60 (3)C3F—N1F—C1F109.4 (2)
Cl1B—Zn1B—Cl4B111.11 (3)C2F—N1F—C4F109.3 (2)
Cl1B—Zn1B—Cl3B109.08 (3)C3F—N1F—C4F108.9 (2)
Cl4B—Zn1B—Cl3B108.58 (3)C1F—N1F—C4F110.0 (2)
Cl1B—Zn1B—Cl2B110.23 (3)C1G—N1G—C2G109.9 (2)
Cl4B—Zn1B—Cl2B107.37 (3)C1G—N1G—C3G109.1 (2)
Cl3B—Zn1B—Cl2B110.46 (3)C2G—N1G—C3G109.3 (2)
Cl1C—Zn1C—Cl2C112.21 (3)C1G—N1G—C4G108.9 (2)
Cl1C—Zn1C—Cl3C109.88 (3)C2G—N1G—C4G109.50 (19)
Cl2C—Zn1C—Cl3C108.62 (3)C3G—N1G—C4G110.1 (2)
Cl1C—Zn1C—Cl4C109.08 (3)C2H—N1H—C3H108.9 (2)
Cl2C—Zn1C—Cl4C108.55 (3)C2H—N1H—C4H110.7 (2)
Cl3C—Zn1C—Cl4C108.42 (3)C3H—N1H—C4H108.5 (2)
C4D—N1D—C3D109.7 (2)C2H—N1H—C1H109.7 (2)
C4D—N1D—C1D109.4 (2)C3H—N1H—C1H109.81 (19)
C3D—N1D—C1D109.11 (19)C1I—N1I—C3I109.2 (2)
C4D—N1D—C2D109.8 (2)C1I—N1I—C2I109.63 (19)
C3D—N1D—C2D109.2 (2)C3I—N1I—C2I110.0 (2)
C1D—N1D—C2D109.54 (19)C1I—N1I—C4I109.6 (2)
C2E—N1E—C4E109.5 (2)C3I—N1I—C4I109.4 (2)
C2E—N1E—C1E110.2 (2)C2I—N1I—C4I109.0 (2)
C4E—N1E—C1E109.4 (2)
Acknowledgements top

Financial support from the Welch Foundation in the form of grant No. AX-1540 is greatly appreciated. The authors thank the National Science Foundation (grant No. CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer and computers used in this work.

references
References top

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Madariaga, G., Zuñiga, F. J., Pérez-Mato, J. M. & Tello, M. J. (1987). Acta Cryst. B43, 356–368.

Ruiz-Larrea, I., Lopez-Echarri, A. & Tello, M. J. (1981). J. Phys. C: Solid State Phys. 14, 3171–3176.

Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2007). SADABS. Version 2007/4. University of Göttingen, Germany.

Wiesner, J. R., Srivastava, R. C., Kennard, C. H. L., Di Vaira, M. & Lingafelter, E. C. (1967). Acta Cryst. 23, 565–574.

Zhang, X.-M. & Bordwell, F. C. (1994). J. Am. Chem. Soc. 116, 968–972.

Zuñiga, F. J., Madariaga, G. & Pérez-Mato, J. M. (1989). Acta Cryst. B45, 462–466.