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The reaction of propane-1,3-diamine hydro­chloride, 18-crown-6 and zinc(II) chloride in methanol solution yields the title complex salt [systematic name: propane-1,3-diaminium tetra­chloridozincate(II)-1,4,7,10,13,16-hexa­oxacyclo­octa­decane (1/1)], (C3H12N2)[ZnCl4]·C12H24O6, with an unusual supra­molecular structure. The diprotonated propane-1,3-di­aminium cation forms an unexpected 1:1 supra­molecular rotator-stator complex with the crown ether, viz. [C3H12N2(18-crown-6)]2+, in which one of the -NH3+ substituents nests in the crown and inter­acts through N-H...O hydrogen bonding. The other -NH3+ group inter­acts with the [ZnCl4]2- anion via N-H...Cl hydrogen bonding, forming cation-crown-anion ribbons parallel to [010].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110022201/sq3249sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110022201/sq3249Isup2.hkl
Contains datablock I

CCDC reference: 786802

Computing details top

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).

propane-1,3-diaminium tetrachloridozincate(II)– 1,4,7,10,13,16-hexaoxacyclooctadecane (1/1) top
Crystal data top
(C3H12N2)[ZnCl4]·C12H24O6F(000) = 1144
Mr = 547.65Dx = 1.452 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6712 reflections
a = 9.134 (3) Åθ = 2.2–27.5°
b = 9.862 (3) ŵ = 1.44 mm1
c = 27.810 (8) ÅT = 93 K
V = 2505.1 (13) Å3Block, colourless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer
5729 independent reflections
Radiation source: fine-focus sealed tube5432 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.2°
CCD_Profile_fitting scansh = 1111
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1212
Tmin = 0.602, Tmax = 0.750l = 3636
24776 measured reflections
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)] = 0.029H-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 reflectionsΔρmax = 0.47 e Å3
253 parametersΔρmin = 0.52 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.003 (11)
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.46558 (4)0.65561 (4)0.161731 (12)0.01562 (9)
Cl40.67684 (8)0.69672 (8)0.20614 (3)0.01763 (16)
Cl30.46586 (9)0.78186 (8)0.09510 (2)0.02090 (16)
Cl20.43509 (8)0.42960 (8)0.15330 (3)0.02101 (17)
Cl10.29348 (9)0.71748 (9)0.21838 (3)0.02212 (17)
O10.9391 (2)0.3326 (2)0.15619 (7)0.0194 (5)
N20.7991 (3)0.1513 (3)0.08904 (8)0.0155 (5)
H2A0.79440.19000.06020.023*
H2B0.84380.07150.08660.023*
H2C0.84920.20460.10890.023*
C110.7052 (4)0.4743 (3)0.03805 (12)0.0206 (7)
H11A0.69510.57120.03310.025*
H11B0.61730.44150.05380.025*
O60.8302 (2)0.4474 (2)0.06755 (7)0.0195 (5)
C130.6479 (3)0.1311 (3)0.10813 (10)0.0158 (6)
H13A0.59260.07390.08630.019*
H13B0.59840.21790.11040.019*
O21.0464 (3)0.0700 (2)0.15335 (8)0.0245 (5)
O40.8237 (2)0.0038 (2)0.00096 (8)0.0208 (5)
O50.7145 (3)0.2623 (2)0.00182 (8)0.0189 (5)
O30.9304 (2)0.1156 (2)0.08594 (8)0.0223 (5)
C71.0446 (4)0.1449 (4)0.19705 (12)0.0263 (7)
H7A1.12460.11600.21760.032*
H7B0.95340.12910.21400.032*
C90.9456 (3)0.4735 (3)0.14473 (11)0.0210 (7)
H9A1.03530.49330.12750.025*
H9B0.94430.52700.17400.025*
C30.8051 (4)0.1430 (3)0.01154 (12)0.0230 (7)
H3A0.79870.19780.01730.028*
H3B0.71540.15460.02980.028*
C20.7165 (4)0.0405 (4)0.03512 (12)0.0258 (8)
H2D0.61900.02640.02230.031*
H2E0.72580.01130.06460.031*
C140.6544 (3)0.0652 (3)0.15737 (10)0.0176 (6)
H14A0.71830.11790.17800.021*
H14B0.69610.02490.15430.021*
C61.0379 (4)0.0717 (4)0.16237 (13)0.0311 (8)
H6A0.94420.09370.17690.037*
H6B1.11480.09870.18440.037*
C120.7243 (4)0.4040 (3)0.00941 (12)0.0235 (7)
H12A0.64890.43320.03170.028*
H12B0.81900.42670.02310.028*
C40.9342 (4)0.1867 (3)0.04120 (12)0.0240 (7)
H4A0.93010.28360.04690.029*
H4B1.02440.16630.02430.029*
C51.0544 (4)0.1450 (4)0.11593 (14)0.0294 (8)
H5A1.14370.11650.10000.035*
H5B1.06040.24190.12170.035*
N10.5215 (3)0.0153 (3)0.22817 (9)0.0190 (5)
H1A0.43440.02250.24230.028*
H1B0.58130.03280.24680.028*
H1C0.55890.09760.22360.028*
C150.5043 (3)0.0545 (3)0.18061 (11)0.0179 (6)
H15A0.46310.14420.18520.022*
H15B0.43880.00300.16010.022*
C100.8150 (4)0.5083 (3)0.11400 (11)0.0199 (7)
H10A0.72630.47560.12930.024*
H10B0.80750.60590.11070.024*
C81.0600 (4)0.2922 (4)0.18556 (12)0.0255 (7)
H8A1.06120.34500.21500.031*
H8C1.15130.30810.16860.031*
C10.7401 (4)0.1886 (4)0.04528 (11)0.0261 (8)
H1D0.83940.20380.05630.031*
H1E0.67320.21890.07010.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01578 (18)0.01615 (17)0.01495 (16)0.00069 (15)0.00042 (14)0.00005 (13)
Cl40.0167 (4)0.0181 (4)0.0181 (3)0.0013 (3)0.0024 (3)0.0014 (3)
Cl30.0250 (4)0.0222 (4)0.0154 (3)0.0027 (4)0.0021 (3)0.0025 (3)
Cl20.0214 (4)0.0171 (4)0.0245 (4)0.0039 (3)0.0019 (3)0.0022 (3)
Cl10.0197 (4)0.0244 (4)0.0222 (4)0.0086 (3)0.0045 (3)0.0043 (3)
O10.0166 (11)0.0208 (11)0.0209 (11)0.0011 (9)0.0048 (9)0.0009 (9)
N20.0169 (13)0.0143 (12)0.0152 (12)0.0011 (12)0.0006 (10)0.0014 (10)
C110.0224 (17)0.0135 (15)0.0258 (16)0.0036 (14)0.0040 (13)0.0002 (13)
O60.0214 (12)0.0197 (11)0.0175 (10)0.0028 (10)0.0004 (9)0.0017 (9)
C130.0127 (14)0.0172 (15)0.0176 (14)0.0006 (12)0.0002 (11)0.0011 (12)
O20.0236 (12)0.0214 (12)0.0286 (12)0.0015 (11)0.0060 (10)0.0049 (10)
O40.0230 (12)0.0173 (11)0.0222 (11)0.0011 (10)0.0001 (9)0.0019 (9)
O50.0282 (12)0.0143 (11)0.0143 (10)0.0034 (10)0.0002 (9)0.0005 (8)
O30.0182 (12)0.0195 (12)0.0291 (12)0.0045 (10)0.0011 (9)0.0014 (9)
C70.0212 (17)0.0358 (19)0.0219 (16)0.0007 (17)0.0075 (13)0.0039 (14)
C90.0191 (17)0.0200 (16)0.0238 (15)0.0017 (14)0.0016 (13)0.0054 (12)
C30.0246 (17)0.0166 (16)0.0278 (16)0.0025 (15)0.0065 (14)0.0047 (14)
C20.0296 (19)0.0275 (19)0.0204 (16)0.0020 (16)0.0047 (14)0.0067 (14)
C140.0179 (15)0.0192 (15)0.0159 (14)0.0010 (13)0.0013 (12)0.0017 (12)
C60.0269 (18)0.0284 (19)0.0380 (19)0.0040 (17)0.0113 (18)0.0114 (16)
C120.0321 (19)0.0182 (16)0.0203 (15)0.0016 (15)0.0036 (14)0.0050 (13)
C40.0239 (18)0.0131 (15)0.0351 (18)0.0008 (14)0.0109 (14)0.0005 (13)
C50.0211 (18)0.0177 (16)0.049 (2)0.0066 (15)0.0075 (16)0.0069 (16)
N10.0207 (13)0.0169 (13)0.0193 (13)0.0023 (12)0.0037 (11)0.0016 (10)
C150.0181 (16)0.0190 (15)0.0168 (14)0.0004 (13)0.0027 (11)0.0009 (12)
C100.0193 (16)0.0169 (15)0.0233 (16)0.0004 (14)0.0047 (13)0.0038 (13)
C80.0183 (17)0.0351 (19)0.0230 (16)0.0020 (16)0.0097 (13)0.0031 (14)
C10.035 (2)0.0270 (19)0.0160 (15)0.0061 (16)0.0024 (14)0.0030 (13)
Geometric parameters (Å, º) top
Zn1—Cl32.2323 (9)C9—H9B0.9700
Zn1—Cl22.2585 (10)C3—C41.502 (5)
Zn1—Cl12.3076 (9)C3—H3A0.9700
Zn1—Cl42.3267 (9)C3—H3B0.9700
O1—C91.427 (4)C2—C11.503 (5)
O1—C81.430 (4)C2—H2D0.9700
N2—C131.493 (4)C2—H2E0.9700
N2—H2A0.8900C14—C151.519 (4)
N2—H2B0.8900C14—H14A0.9700
N2—H2C0.8900C14—H14B0.9700
C11—O61.431 (4)C6—C51.488 (5)
C11—C121.501 (4)C6—H6A0.9700
C11—H11A0.9700C6—H6B0.9700
C11—H11B0.9700C12—H12A0.9700
O6—C101.431 (4)C12—H12B0.9700
C13—C141.517 (4)C4—H4A0.9700
C13—H13A0.9700C4—H4B0.9700
C13—H13B0.9700C5—H5A0.9700
O2—C61.422 (4)C5—H5B0.9700
O2—C71.422 (4)N1—C151.499 (4)
O4—C31.426 (4)N1—H1A0.8900
O4—C21.433 (4)N1—H1B0.8900
O5—C121.417 (4)N1—H1C0.8900
O5—C11.429 (4)C15—H15A0.9700
O3—C41.428 (4)C15—H15B0.9700
O3—C51.436 (4)C10—H10A0.9700
C7—C81.494 (5)C10—H10B0.9700
C7—H7A0.9700C8—H8A0.9700
C7—H7B0.9700C8—H8C0.9700
C9—C101.507 (4)C1—H1D0.9700
C9—H9A0.9700C1—H1E0.9700
Cl3—Zn1—Cl2117.67 (3)C13—C14—H14B109.2
Cl3—Zn1—Cl1114.84 (4)C15—C14—H14B109.2
Cl2—Zn1—Cl1104.35 (3)H14A—C14—H14B107.9
Cl3—Zn1—Cl4110.03 (3)O2—C6—C5108.6 (3)
Cl2—Zn1—Cl4109.23 (3)O2—C6—H6A110.0
Cl1—Zn1—Cl499.00 (4)C5—C6—H6A110.0
C9—O1—C8111.5 (2)O2—C6—H6B110.0
C13—N2—H2A109.5C5—C6—H6B110.0
C13—N2—H2B109.5H6A—C6—H6B108.3
H2A—N2—H2B109.5O5—C12—C11108.5 (3)
C13—N2—H2C109.5O5—C12—H12A110.0
H2A—N2—H2C109.5C11—C12—H12A110.0
H2B—N2—H2C109.5O5—C12—H12B110.0
O6—C11—C12109.0 (3)C11—C12—H12B110.0
O6—C11—H11A109.9H12A—C12—H12B108.4
C12—C11—H11A109.9O3—C4—C3108.6 (3)
O6—C11—H11B109.9O3—C4—H4A110.0
C12—C11—H11B109.9C3—C4—H4A110.0
H11A—C11—H11B108.3O3—C4—H4B110.0
C11—O6—C10111.3 (2)C3—C4—H4B110.0
N2—C13—C14110.0 (2)H4A—C4—H4B108.4
N2—C13—H13A109.7O3—C5—C6109.0 (3)
C14—C13—H13A109.7O3—C5—H5A109.9
N2—C13—H13B109.7C6—C5—H5A109.9
C14—C13—H13B109.7O3—C5—H5B109.9
H13A—C13—H13B108.2C6—C5—H5B109.9
C6—O2—C7111.0 (3)H5A—C5—H5B108.3
C3—O4—C2112.0 (3)C15—N1—H1A109.5
C12—O5—C1111.4 (3)C15—N1—H1B109.5
C4—O3—C5112.8 (3)H1A—N1—H1B109.5
O2—C7—C8108.7 (3)C15—N1—H1C109.5
O2—C7—H7A109.9H1A—N1—H1C109.5
C8—C7—H7A109.9H1B—N1—H1C109.5
O2—C7—H7B109.9N1—C15—C14108.2 (2)
C8—C7—H7B109.9N1—C15—H15A110.1
H7A—C7—H7B108.3C14—C15—H15A110.1
O1—C9—C10108.4 (3)N1—C15—H15B110.1
O1—C9—H9A110.0C14—C15—H15B110.1
C10—C9—H9A110.0H15A—C15—H15B108.4
O1—C9—H9B110.0O6—C10—C9109.9 (3)
C10—C9—H9B110.0O6—C10—H10A109.7
H9A—C9—H9B108.4C9—C10—H10A109.7
O4—C3—C4108.4 (3)O6—C10—H10B109.7
O4—C3—H3A110.0C9—C10—H10B109.7
C4—C3—H3A110.0H10A—C10—H10B108.2
O4—C3—H3B110.0O1—C8—C7108.7 (3)
C4—C3—H3B110.0O1—C8—H8A110.0
H3A—C3—H3B108.4C7—C8—H8A110.0
O4—C2—C1108.9 (3)O1—C8—H8C110.0
O4—C2—H2D109.9C7—C8—H8C110.0
C1—C2—H2D109.9H8A—C8—H8C108.3
O4—C2—H2E109.9O5—C1—C2108.2 (3)
C1—C2—H2E109.9O5—C1—H1D110.1
H2D—C2—H2E108.3C2—C1—H1D110.1
C13—C14—C15112.2 (2)O5—C1—H1E110.1
C13—C14—H14A109.2C2—C1—H1E110.1
C15—C14—H14A109.2H1D—C1—H1E108.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2C···O10.892.002.884 (3)173
N2—H2C···O20.892.562.991 (3)111
N2—H2B···O30.892.012.894 (4)174
N2—H2B···O40.892.552.942 (3)107
N2—H2A···O50.892.002.860 (3)161
N2—H2A···O60.892.572.994 (4)110
N1—H1C···Cl4i0.892.353.233 (3)174
N1—H1A···Cl4ii0.892.793.315 (3)120
N1—H1A···Cl1i0.892.953.370 (3)111
N1—H1B···Cl1ii0.892.363.215 (3)162
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1/2.
 

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