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The title compound, (C4H14N2)[HgCl4], contains layers of tilted corner-sharing chloro­mercurate octahedra. Each HgII ion lies on a center of symmetry, and has four long bonds to the halide ions, forming puckered sheets parallel to the bc plane plus two short bonds to halide ions axial to the sheets, completing a tetragonally compressed octahedral coordination. Adjacent sheets have axial halide ions in an eclipsed conformation. The di­ammonium ions provide links between sheets, hydrogen bonding to the halides. The organic chains have the two ends of the di­ammonium ions equivalent by a center of symmetry, with C4 chains trans around the central bond and gauche for N versus C positioning around each terminal C-C bond. No phase transition before the decomposition temperature has been detected by differential scanning calorimetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201067X/ob6139sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201067X/ob6139Isup2.hkl
Contains datablock I

CCDC reference: 189873

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.018 Å
  • R factor = 0.036
  • wR factor = 0.073
  • Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found


Amber Alert Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5599
Author response: It is noticed that zero intensity was observed for the reflections at higher angles, which is a characteristic behavior of this family of organo-metallic compound (Spengler et al., 1998, Zouari et al.1998).
PLAT_112  Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem.          A
Author response: The symmetry of these first layer of the structure taken alone is A2/m. The 4DA chains building the second layer of the structure have only the P21/c symmetry.

Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 23.45 From the CIF: _reflns_number_total 741 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 802 Completeness (_total/calc) 92.39% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: local software (Huber, 2000); cell refinement: MACH3 in CAD-4 UNIX Software (Enraf-Nonius, 1998); data reduction: local software (Huber, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).

Bis-buthanediammoniumchloride tetrachloromercurate top
Crystal data top
(C4H14N2)[HgCl4]F(000) = 400
Mr = 432.56Dx = 2.629 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.082 (2) ÅCell parameters from 25 reflections
b = 7.720 (5) Åθ = 10–25°
c = 7.996 (5) ŵ = 15.01 mm1
β = 102.907 (12)°T = 293 K
V = 546.5 (5) Å3Polyhedral, colorless
Z = 20.40 × 0.32 × 0.25 mm
Data collection top
Home-made (Huber, 2000) Image Plate
diffractometer
741 independent reflections
Radiation source: fine-focus sealed tube571 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: Image Plate detector pixels mm-1θmax = 23.5°, θmin = 3.5°
ω–scanh = 109
Absorption correction: integration
(local program; Hertlein, 1989)
k = 08
Tmin = 0.026, Tmax = 0.463l = 08
803 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)] = 0.036H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
741 reflectionsΔρmax = 1.46 e Å3
53 parametersΔρmin = 1.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.111 (6)
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.

Refinement. Full experimental details are given in Table1. A colorless crystal of dimension 0.4x 0.3 x0.35 mm3 was used for X-ray scattering on a home made Image plate diffractometer (Huber, T., 2000) using graphite-monochromated Mo Ka radiation (λ = 0.70926 Å). The monoclinic lattice constants were obtained as a = 9.082 (2) b= 7.720 (5) c = 7.996 (5) β = 102.907 (12). For the data collection 61–121 data frames were collected by 3° steps in ω-scan with exposure time of 500 second and crystal to detector distance of 12 cm. 8518 reflections were measured. The intensity data were averaged in laue symmetry 2/m resulting in 741 independents reflections 571 reflections with I>2σ(I). The analysis of the systematic absences showed the reflection condition to be valid for a c glide perpendicular to the unique axis b, h0l: l = 2n and for a tow helicoidal axis parallel to b axis 0k0: k = 2n. The space group compatible with these conditions is P21/c. The structure refinement was performed using the program SHELXL97 (Sheldrick, 1997). The refinement converge to a structure model with R(F) = 0.0360, WR(F) = 0.0727. Patterson mapping found heavy atom positions. The C and N atoms were found on difference Fourier maps and included in the calculations. All the non-hydrogen atoms were anisotropically refined.

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
xyzUiso*/Ueq
Hg0.00000.00000.00000.0255 (5)
Cl10.2697 (3)0.0551 (4)0.0535 (4)0.0362 (9)
Cl20.0399 (3)0.2326 (3)0.2742 (3)0.0350 (9)
N10.2203 (12)0.0275 (11)0.5684 (16)0.045 (3)
H1A0.15590.01590.63670.067*
H1B0.17990.01750.46590.067*
H1C0.23960.13940.55680.067*
C10.3626 (15)0.0643 (18)0.6443 (17)0.044 (3)
H1D0.33910.17850.68180.053*
H1E0.41640.00110.74420.053*
C20.4633 (14)0.0824 (17)0.5167 (14)0.037 (3)
H2A0.54120.16740.56000.045*
H2B0.40320.12590.40910.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg0.0223 (6)0.0259 (6)0.0291 (6)0.0044 (3)0.0077 (3)0.0002 (3)
Cl10.0212 (17)0.0314 (18)0.055 (2)0.0034 (13)0.0065 (14)0.0043 (15)
Cl20.0379 (19)0.0329 (18)0.0371 (17)0.0081 (15)0.0143 (14)0.0138 (16)
N10.023 (6)0.035 (6)0.084 (9)0.006 (4)0.027 (6)0.014 (6)
C10.038 (9)0.053 (7)0.047 (8)0.005 (7)0.017 (7)0.009 (7)
C20.045 (8)0.029 (6)0.042 (8)0.011 (6)0.019 (6)0.007 (6)
Geometric parameters (Å, º) top
Hg—Cl12.428 (3)N1—H1B0.8900
Hg—Cl1i2.428 (3)N1—H1C0.8900
Hg—Cl2i2.794 (3)C1—C21.521 (17)
Hg—Cl22.794 (3)C1—H1D0.9700
Hg—Cl2ii2.819 (3)C1—H1E0.9700
Hg—Cl2iii2.819 (3)C2—C2v1.49 (3)
Cl2—Hgiv2.819 (3)C2—H2A0.9700
N1—C11.480 (17)C2—H2B0.9700
N1—H1A0.8900
Cl1—Hg—Cl1i180.00 (3)C1—N1—H1B109.5
Cl1—Hg—Cl2i91.46 (10)H1A—N1—H1B109.5
Cl1i—Hg—Cl2i88.54 (10)C1—N1—H1C109.5
Cl1—Hg—Cl288.54 (10)H1A—N1—H1C109.5
Cl1i—Hg—Cl291.46 (10)H1B—N1—H1C109.5
Cl2i—Hg—Cl2180.0N1—C1—C2111.7 (10)
Cl1—Hg—Cl2ii91.60 (10)N1—C1—H1D109.3
Cl1i—Hg—Cl2ii88.40 (10)C2—C1—H1D109.3
Cl2i—Hg—Cl2ii88.90 (5)N1—C1—H1E109.3
Cl2—Hg—Cl2ii91.10 (5)C2—C1—H1E109.3
Cl1—Hg—Cl2iii88.40 (10)H1D—C1—H1E107.9
Cl1i—Hg—Cl2iii91.60 (10)C2v—C2—C1113.7 (14)
Cl2i—Hg—Cl2iii91.10 (5)C2v—C2—H2A108.8
Cl2—Hg—Cl2iii88.90 (5)C1—C2—H2A108.8
Cl2ii—Hg—Cl2iii180.00 (8)C2v—C2—H2B108.8
Hg—Cl2—Hgiv163.86 (13)C1—C2—H2B108.8
C1—N1—H1A109.5H2A—C2—H2B107.7
N1—C1—C2—C2v73.1 (13)C1—C2—C2v—C1v180
Symmetry codes: (i) x, y, z; (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z1/2; (iv) x, y+1/2, z1/2; (v) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl2vi0.892.763.432 (11)133
N1—H1B···Cl2i0.892.423.245 (11)154
N1—H1C···Cl1ii0.892.383.259 (9)172
Symmetry codes: (i) x, y, z; (ii) x, y+1/2, z+1/2; (vi) x, y1/2, z+1/2.
 

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