Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110022201/sq3249sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022201/sq3249Isup2.hkl |
CCDC reference: 786802
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: PRPKAPPA (Ferguson, 1999).
(C3H12N2)[ZnCl4]·C12H24O6 | F(000) = 1144 |
Mr = 547.65 | Dx = 1.452 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6712 reflections |
a = 9.134 (3) Å | θ = 2.2–27.5° |
b = 9.862 (3) Å | µ = 1.44 mm−1 |
c = 27.810 (8) Å | T = 93 K |
V = 2505.1 (13) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
Rigaku SCXmini diffractometer | 5729 independent reflections |
Radiation source: fine-focus sealed tube | 5432 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
CCD_Profile_fitting scans | h = −11→11 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −12→12 |
Tmin = 0.602, Tmax = 0.750 | l = −36→36 |
24776 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0471P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
5729 reflections | Δρmax = 0.47 e Å−3 |
253 parameters | Δρmin = −0.52 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.003 (11) |
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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.46558 (4) | 0.65561 (4) | 0.161731 (12) | 0.01562 (9) | |
Cl4 | 0.67684 (8) | 0.69672 (8) | 0.20614 (3) | 0.01763 (16) | |
Cl3 | 0.46586 (9) | 0.78186 (8) | 0.09510 (2) | 0.02090 (16) | |
Cl2 | 0.43509 (8) | 0.42960 (8) | 0.15330 (3) | 0.02101 (17) | |
Cl1 | 0.29348 (9) | 0.71748 (9) | 0.21838 (3) | 0.02212 (17) | |
O1 | 0.9391 (2) | 0.3326 (2) | 0.15619 (7) | 0.0194 (5) | |
N2 | 0.7991 (3) | 0.1513 (3) | 0.08904 (8) | 0.0155 (5) | |
H2A | 0.7944 | 0.1900 | 0.0602 | 0.023* | |
H2B | 0.8438 | 0.0715 | 0.0866 | 0.023* | |
H2C | 0.8492 | 0.2046 | 0.1089 | 0.023* | |
C11 | 0.7052 (4) | 0.4743 (3) | 0.03805 (12) | 0.0206 (7) | |
H11A | 0.6951 | 0.5712 | 0.0331 | 0.025* | |
H11B | 0.6173 | 0.4415 | 0.0538 | 0.025* | |
O6 | 0.8302 (2) | 0.4474 (2) | 0.06755 (7) | 0.0195 (5) | |
C13 | 0.6479 (3) | 0.1311 (3) | 0.10813 (10) | 0.0158 (6) | |
H13A | 0.5926 | 0.0739 | 0.0863 | 0.019* | |
H13B | 0.5984 | 0.2179 | 0.1104 | 0.019* | |
O2 | 1.0464 (3) | 0.0700 (2) | 0.15335 (8) | 0.0245 (5) | |
O4 | 0.8237 (2) | −0.0038 (2) | −0.00096 (8) | 0.0208 (5) | |
O5 | 0.7145 (3) | 0.2623 (2) | −0.00182 (8) | 0.0189 (5) | |
O3 | 0.9304 (2) | −0.1156 (2) | 0.08594 (8) | 0.0223 (5) | |
C7 | 1.0446 (4) | 0.1449 (4) | 0.19705 (12) | 0.0263 (7) | |
H7A | 1.1246 | 0.1160 | 0.2176 | 0.032* | |
H7B | 0.9534 | 0.1291 | 0.2140 | 0.032* | |
C9 | 0.9456 (3) | 0.4735 (3) | 0.14473 (11) | 0.0210 (7) | |
H9A | 1.0353 | 0.4933 | 0.1275 | 0.025* | |
H9B | 0.9443 | 0.5270 | 0.1740 | 0.025* | |
C3 | 0.8051 (4) | −0.1430 (3) | 0.01154 (12) | 0.0230 (7) | |
H3A | 0.7987 | −0.1978 | −0.0173 | 0.028* | |
H3B | 0.7154 | −0.1546 | 0.0298 | 0.028* | |
C2 | 0.7165 (4) | 0.0405 (4) | −0.03512 (12) | 0.0258 (8) | |
H2D | 0.6190 | 0.0264 | −0.0223 | 0.031* | |
H2E | 0.7258 | −0.0113 | −0.0646 | 0.031* | |
C14 | 0.6544 (3) | 0.0652 (3) | 0.15737 (10) | 0.0176 (6) | |
H14A | 0.7183 | 0.1179 | 0.1780 | 0.021* | |
H14B | 0.6961 | −0.0249 | 0.1543 | 0.021* | |
C6 | 1.0379 (4) | −0.0717 (4) | 0.16237 (13) | 0.0311 (8) | |
H6A | 0.9442 | −0.0937 | 0.1769 | 0.037* | |
H6B | 1.1148 | −0.0987 | 0.1844 | 0.037* | |
C12 | 0.7243 (4) | 0.4040 (3) | −0.00941 (12) | 0.0235 (7) | |
H12A | 0.6489 | 0.4332 | −0.0317 | 0.028* | |
H12B | 0.8190 | 0.4267 | −0.0231 | 0.028* | |
C4 | 0.9342 (4) | −0.1867 (3) | 0.04120 (12) | 0.0240 (7) | |
H4A | 0.9301 | −0.2836 | 0.0469 | 0.029* | |
H4B | 1.0244 | −0.1663 | 0.0243 | 0.029* | |
C5 | 1.0544 (4) | −0.1450 (4) | 0.11593 (14) | 0.0294 (8) | |
H5A | 1.1437 | −0.1165 | 0.1000 | 0.035* | |
H5B | 1.0604 | −0.2419 | 0.1217 | 0.035* | |
N1 | 0.5215 (3) | −0.0153 (3) | 0.22817 (9) | 0.0190 (5) | |
H1A | 0.4344 | −0.0225 | 0.2423 | 0.028* | |
H1B | 0.5813 | 0.0328 | 0.2468 | 0.028* | |
H1C | 0.5589 | −0.0976 | 0.2236 | 0.028* | |
C15 | 0.5043 (3) | 0.0545 (3) | 0.18061 (11) | 0.0179 (6) | |
H15A | 0.4631 | 0.1442 | 0.1852 | 0.022* | |
H15B | 0.4388 | 0.0030 | 0.1601 | 0.022* | |
C10 | 0.8150 (4) | 0.5083 (3) | 0.11400 (11) | 0.0199 (7) | |
H10A | 0.7263 | 0.4756 | 0.1293 | 0.024* | |
H10B | 0.8075 | 0.6059 | 0.1107 | 0.024* | |
C8 | 1.0600 (4) | 0.2922 (4) | 0.18556 (12) | 0.0255 (7) | |
H8A | 1.0612 | 0.3450 | 0.2150 | 0.031* | |
H8C | 1.1513 | 0.3081 | 0.1686 | 0.031* | |
C1 | 0.7401 (4) | 0.1886 (4) | −0.04528 (11) | 0.0261 (8) | |
H1D | 0.8394 | 0.2038 | −0.0563 | 0.031* | |
H1E | 0.6732 | 0.2189 | −0.0701 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01578 (18) | 0.01615 (17) | 0.01495 (16) | 0.00069 (15) | −0.00042 (14) | 0.00005 (13) |
Cl4 | 0.0167 (4) | 0.0181 (4) | 0.0181 (3) | 0.0013 (3) | −0.0024 (3) | −0.0014 (3) |
Cl3 | 0.0250 (4) | 0.0222 (4) | 0.0154 (3) | −0.0027 (4) | −0.0021 (3) | 0.0025 (3) |
Cl2 | 0.0214 (4) | 0.0171 (4) | 0.0245 (4) | −0.0039 (3) | 0.0019 (3) | −0.0022 (3) |
Cl1 | 0.0197 (4) | 0.0244 (4) | 0.0222 (4) | 0.0086 (3) | 0.0045 (3) | 0.0043 (3) |
O1 | 0.0166 (11) | 0.0208 (11) | 0.0209 (11) | −0.0011 (9) | −0.0048 (9) | 0.0009 (9) |
N2 | 0.0169 (13) | 0.0143 (12) | 0.0152 (12) | 0.0011 (12) | 0.0006 (10) | 0.0014 (10) |
C11 | 0.0224 (17) | 0.0135 (15) | 0.0258 (16) | 0.0036 (14) | −0.0040 (13) | 0.0002 (13) |
O6 | 0.0214 (12) | 0.0197 (11) | 0.0175 (10) | 0.0028 (10) | 0.0004 (9) | −0.0017 (9) |
C13 | 0.0127 (14) | 0.0172 (15) | 0.0176 (14) | −0.0006 (12) | −0.0002 (11) | 0.0011 (12) |
O2 | 0.0236 (12) | 0.0214 (12) | 0.0286 (12) | 0.0015 (11) | −0.0060 (10) | 0.0049 (10) |
O4 | 0.0230 (12) | 0.0173 (11) | 0.0222 (11) | −0.0011 (10) | 0.0001 (9) | −0.0019 (9) |
O5 | 0.0282 (12) | 0.0143 (11) | 0.0143 (10) | 0.0034 (10) | −0.0002 (9) | −0.0005 (8) |
O3 | 0.0182 (12) | 0.0195 (12) | 0.0291 (12) | 0.0045 (10) | 0.0011 (9) | 0.0014 (9) |
C7 | 0.0212 (17) | 0.0358 (19) | 0.0219 (16) | −0.0007 (17) | −0.0075 (13) | 0.0039 (14) |
C9 | 0.0191 (17) | 0.0200 (16) | 0.0238 (15) | −0.0017 (14) | 0.0016 (13) | −0.0054 (12) |
C3 | 0.0246 (17) | 0.0166 (16) | 0.0278 (16) | −0.0025 (15) | 0.0065 (14) | −0.0047 (14) |
C2 | 0.0296 (19) | 0.0275 (19) | 0.0204 (16) | 0.0020 (16) | −0.0047 (14) | −0.0067 (14) |
C14 | 0.0179 (15) | 0.0192 (15) | 0.0159 (14) | 0.0010 (13) | −0.0013 (12) | 0.0017 (12) |
C6 | 0.0269 (18) | 0.0284 (19) | 0.0380 (19) | 0.0040 (17) | −0.0113 (18) | 0.0114 (16) |
C12 | 0.0321 (19) | 0.0182 (16) | 0.0203 (15) | 0.0016 (15) | −0.0036 (14) | 0.0050 (13) |
C4 | 0.0239 (18) | 0.0131 (15) | 0.0351 (18) | 0.0008 (14) | 0.0109 (14) | −0.0005 (13) |
C5 | 0.0211 (18) | 0.0177 (16) | 0.049 (2) | 0.0066 (15) | −0.0075 (16) | 0.0069 (16) |
N1 | 0.0207 (13) | 0.0169 (13) | 0.0193 (13) | −0.0023 (12) | 0.0037 (11) | −0.0016 (10) |
C15 | 0.0181 (16) | 0.0190 (15) | 0.0168 (14) | −0.0004 (13) | 0.0027 (11) | 0.0009 (12) |
C10 | 0.0193 (16) | 0.0169 (15) | 0.0233 (16) | 0.0004 (14) | 0.0047 (13) | −0.0038 (13) |
C8 | 0.0183 (17) | 0.0351 (19) | 0.0230 (16) | −0.0020 (16) | −0.0097 (13) | −0.0031 (14) |
C1 | 0.035 (2) | 0.0270 (19) | 0.0160 (15) | 0.0061 (16) | −0.0024 (14) | −0.0030 (13) |
Zn1—Cl3 | 2.2323 (9) | C9—H9B | 0.9700 |
Zn1—Cl2 | 2.2585 (10) | C3—C4 | 1.502 (5) |
Zn1—Cl1 | 2.3076 (9) | C3—H3A | 0.9700 |
Zn1—Cl4 | 2.3267 (9) | C3—H3B | 0.9700 |
O1—C9 | 1.427 (4) | C2—C1 | 1.503 (5) |
O1—C8 | 1.430 (4) | C2—H2D | 0.9700 |
N2—C13 | 1.493 (4) | C2—H2E | 0.9700 |
N2—H2A | 0.8900 | C14—C15 | 1.519 (4) |
N2—H2B | 0.8900 | C14—H14A | 0.9700 |
N2—H2C | 0.8900 | C14—H14B | 0.9700 |
C11—O6 | 1.431 (4) | C6—C5 | 1.488 (5) |
C11—C12 | 1.501 (4) | C6—H6A | 0.9700 |
C11—H11A | 0.9700 | C6—H6B | 0.9700 |
C11—H11B | 0.9700 | C12—H12A | 0.9700 |
O6—C10 | 1.431 (4) | C12—H12B | 0.9700 |
C13—C14 | 1.517 (4) | C4—H4A | 0.9700 |
C13—H13A | 0.9700 | C4—H4B | 0.9700 |
C13—H13B | 0.9700 | C5—H5A | 0.9700 |
O2—C6 | 1.422 (4) | C5—H5B | 0.9700 |
O2—C7 | 1.422 (4) | N1—C15 | 1.499 (4) |
O4—C3 | 1.426 (4) | N1—H1A | 0.8900 |
O4—C2 | 1.433 (4) | N1—H1B | 0.8900 |
O5—C12 | 1.417 (4) | N1—H1C | 0.8900 |
O5—C1 | 1.429 (4) | C15—H15A | 0.9700 |
O3—C4 | 1.428 (4) | C15—H15B | 0.9700 |
O3—C5 | 1.436 (4) | C10—H10A | 0.9700 |
C7—C8 | 1.494 (5) | C10—H10B | 0.9700 |
C7—H7A | 0.9700 | C8—H8A | 0.9700 |
C7—H7B | 0.9700 | C8—H8C | 0.9700 |
C9—C10 | 1.507 (4) | C1—H1D | 0.9700 |
C9—H9A | 0.9700 | C1—H1E | 0.9700 |
Cl3—Zn1—Cl2 | 117.67 (3) | C13—C14—H14B | 109.2 |
Cl3—Zn1—Cl1 | 114.84 (4) | C15—C14—H14B | 109.2 |
Cl2—Zn1—Cl1 | 104.35 (3) | H14A—C14—H14B | 107.9 |
Cl3—Zn1—Cl4 | 110.03 (3) | O2—C6—C5 | 108.6 (3) |
Cl2—Zn1—Cl4 | 109.23 (3) | O2—C6—H6A | 110.0 |
Cl1—Zn1—Cl4 | 99.00 (4) | C5—C6—H6A | 110.0 |
C9—O1—C8 | 111.5 (2) | O2—C6—H6B | 110.0 |
C13—N2—H2A | 109.5 | C5—C6—H6B | 110.0 |
C13—N2—H2B | 109.5 | H6A—C6—H6B | 108.3 |
H2A—N2—H2B | 109.5 | O5—C12—C11 | 108.5 (3) |
C13—N2—H2C | 109.5 | O5—C12—H12A | 110.0 |
H2A—N2—H2C | 109.5 | C11—C12—H12A | 110.0 |
H2B—N2—H2C | 109.5 | O5—C12—H12B | 110.0 |
O6—C11—C12 | 109.0 (3) | C11—C12—H12B | 110.0 |
O6—C11—H11A | 109.9 | H12A—C12—H12B | 108.4 |
C12—C11—H11A | 109.9 | O3—C4—C3 | 108.6 (3) |
O6—C11—H11B | 109.9 | O3—C4—H4A | 110.0 |
C12—C11—H11B | 109.9 | C3—C4—H4A | 110.0 |
H11A—C11—H11B | 108.3 | O3—C4—H4B | 110.0 |
C11—O6—C10 | 111.3 (2) | C3—C4—H4B | 110.0 |
N2—C13—C14 | 110.0 (2) | H4A—C4—H4B | 108.4 |
N2—C13—H13A | 109.7 | O3—C5—C6 | 109.0 (3) |
C14—C13—H13A | 109.7 | O3—C5—H5A | 109.9 |
N2—C13—H13B | 109.7 | C6—C5—H5A | 109.9 |
C14—C13—H13B | 109.7 | O3—C5—H5B | 109.9 |
H13A—C13—H13B | 108.2 | C6—C5—H5B | 109.9 |
C6—O2—C7 | 111.0 (3) | H5A—C5—H5B | 108.3 |
C3—O4—C2 | 112.0 (3) | C15—N1—H1A | 109.5 |
C12—O5—C1 | 111.4 (3) | C15—N1—H1B | 109.5 |
C4—O3—C5 | 112.8 (3) | H1A—N1—H1B | 109.5 |
O2—C7—C8 | 108.7 (3) | C15—N1—H1C | 109.5 |
O2—C7—H7A | 109.9 | H1A—N1—H1C | 109.5 |
C8—C7—H7A | 109.9 | H1B—N1—H1C | 109.5 |
O2—C7—H7B | 109.9 | N1—C15—C14 | 108.2 (2) |
C8—C7—H7B | 109.9 | N1—C15—H15A | 110.1 |
H7A—C7—H7B | 108.3 | C14—C15—H15A | 110.1 |
O1—C9—C10 | 108.4 (3) | N1—C15—H15B | 110.1 |
O1—C9—H9A | 110.0 | C14—C15—H15B | 110.1 |
C10—C9—H9A | 110.0 | H15A—C15—H15B | 108.4 |
O1—C9—H9B | 110.0 | O6—C10—C9 | 109.9 (3) |
C10—C9—H9B | 110.0 | O6—C10—H10A | 109.7 |
H9A—C9—H9B | 108.4 | C9—C10—H10A | 109.7 |
O4—C3—C4 | 108.4 (3) | O6—C10—H10B | 109.7 |
O4—C3—H3A | 110.0 | C9—C10—H10B | 109.7 |
C4—C3—H3A | 110.0 | H10A—C10—H10B | 108.2 |
O4—C3—H3B | 110.0 | O1—C8—C7 | 108.7 (3) |
C4—C3—H3B | 110.0 | O1—C8—H8A | 110.0 |
H3A—C3—H3B | 108.4 | C7—C8—H8A | 110.0 |
O4—C2—C1 | 108.9 (3) | O1—C8—H8C | 110.0 |
O4—C2—H2D | 109.9 | C7—C8—H8C | 110.0 |
C1—C2—H2D | 109.9 | H8A—C8—H8C | 108.3 |
O4—C2—H2E | 109.9 | O5—C1—C2 | 108.2 (3) |
C1—C2—H2E | 109.9 | O5—C1—H1D | 110.1 |
H2D—C2—H2E | 108.3 | C2—C1—H1D | 110.1 |
C13—C14—C15 | 112.2 (2) | O5—C1—H1E | 110.1 |
C13—C14—H14A | 109.2 | C2—C1—H1E | 110.1 |
C15—C14—H14A | 109.2 | H1D—C1—H1E | 108.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···O1 | 0.89 | 2.00 | 2.884 (3) | 173 |
N2—H2C···O2 | 0.89 | 2.56 | 2.991 (3) | 111 |
N2—H2B···O3 | 0.89 | 2.01 | 2.894 (4) | 174 |
N2—H2B···O4 | 0.89 | 2.55 | 2.942 (3) | 107 |
N2—H2A···O5 | 0.89 | 2.00 | 2.860 (3) | 161 |
N2—H2A···O6 | 0.89 | 2.57 | 2.994 (4) | 110 |
N1—H1C···Cl4i | 0.89 | 2.35 | 3.233 (3) | 174 |
N1—H1A···Cl4ii | 0.89 | 2.79 | 3.315 (3) | 120 |
N1—H1A···Cl1i | 0.89 | 2.95 | 3.370 (3) | 111 |
N1—H1B···Cl1ii | 0.89 | 2.36 | 3.215 (3) | 162 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2. |
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