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Acta Cryst. (2007). E63, m1894    [ doi:10.1107/S1600536807027468 ]

1,1'-(Butane-1,4-diyl)dipyridinium bromidotrichloridomercurate(II)

Y.-Y. Niu, X.-C. Liu, H.-W. Hou, Y.-T. Fan and S. W. Ng

Abstract top

The Hg atom in the title compound, (C14H18N2)[HgBrCl3], is coordinated by four halogen atoms in a tetrahedral geometry. The four halogen atoms are each disordered between Br and Cl, with the Br:Cl ratios being 0.218 (2):0.782 (2), 0.136 (2):0.864 (2), 0.090 (2):0.910 (2) and 0.556 (2):0.444 (2). The cation is disordered over two orientations and each was refined with an occupancy of 0.50.

Comment top

The preceding study reports the structure of the tetrahedral dibromidodichloridomercurate(II), which was isolated as a 1,2-ethanedipyridinium salt (Wang et al., 2007). Replacing the cation by 1,4-butanedipyridinium furnishes a similar tetrahalomercurate. The anion of the salt is composed of one bromine and three chlorine atoms which are disordered (Fig. 1); the metal atom shows tetrahedral coordination. Selected bond distances are listed in Table 1.

Related literature top

For related tetrahalogenomercurates, see: Wang et al. (2007).

Experimental top

The salt was synthesized from the reaction of butane-1,4-dipyridinium dibromide (0.026 g, 0.1 mmol) in methanol (5 ml) and mercuric dichloride (0.054 g, 0.2 mmol) in DMF (10 ml). The mixture was set aside for the formation of colourless crystals in 30% yield after several days. CH&N elemental analysis for C14H18BrCl3HgN2. Calculated: C 27.97, H 3.02, N 4.46%; found C 27.08, H 2.77, N 4.49%.

Refinement top

The four halogens lie in general positions. Initial attempts to refine the structure with either four bromines or four chlorines gave unacceptably high R-indices and large peaks/deep holes. The four halogen atoms were then refined as four (Br+Cl) mixtures; one attempt had the mixtures to have the same displacement parameters as well as sharing the same site. A second attempt had the components having the same displacement parameters only. The second led to a formulation consisting of approximately one Br and three Cl atoms. The use of a restraint that fixed the number of Br and Cl atoms as exactly 1 Br and 3 C l led to occupancies of 0.218 (2), 0.136 (2), 0.090 (2) and 0.556 (2), respectively, Br1, Br2, Br3 and Br4, and 0.782 (2), 0.864 (2), 0.910 (2) and 0.444 (2), respectively, for Cl1, Cl2, Cl3 and Cl4. The formulation is in good agreement with CH&N elemental analysis, and furthermore, there were neither large peaks nor deep holes in the difference Fourier map. Other formulations led to somewhat larger peaks/deep holes.

The cation is disordered over two orientations and each was refined with an occupancy of 0.50. The occupancy could not be refined. The pyridyl rings were refined as rigid hexagons (C—C = C—N = 1.39 Å). The C(sp3)—C(sp3) and N—C(sp3) distances were restrained to 1.50 (1) Å, and the 1,3-related distances to 2.45 (1) Å; additionally, the alphatic carbon atom bonded to the nitrogen atom was retrained to lie on the plane of the ring. The displacement parameters of the primed atoms were set to those of the unprimed ones and they were restrained to be nearly isotropic. C-bound H atoms were generated geometrically (C—H 0.93 and 0.97 Å), and were included in the refinement in the riding-model approximation, with U(H) set to 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. The molecular structure of [C14H18N2][HgBrCl3]. Displacement ellipsoids are drawn at the 50% probability level. The bromine and chlorine atoms are disordered; the figure depicts the anion as an [HgX4]2− species. Hydrogen atoms are drawn as spheres of arbitrary radius.
1,1'-(Butane-1,4-diyl)dipyridinium bromidotrichloridomercurate(II) top
Crystal data top
(C14H18N2)[HgBrCl3]F000 = 1128
Mr = 601.15Dx = 2.111 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4607 reflections
a = 15.9912 (8) Åθ = 2.7–26.4º
b = 8.7769 (5) ŵ = 10.67 mm−1
c = 14.3189 (9) ÅT = 295 (2) K
β = 109.760 (1)ºBlock, colourless
V = 1891.4 (2) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer		3316 independent reflections
Radiation source: fine-focus sealed tube2809 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 2.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −19→15
Tmin = 0.096, Tmax = 0.415k = −10→10
11857 measured reflectionsl = −17→17
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)] = 0.031H-atom parameters constrained
wR(F2) = 0.081  w = 1/[σ2(Fo2) + (0.0459P)2 + 0.263P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3316 reflectionsΔρmax = 0.77 e Å−3
210 parametersΔρmin = −0.84 e Å−3
130 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
(C14H18N2)[HgBrCl3]V = 1891.4 (2) Å3
Mr = 601.15Z = 4
Monoclinic, P21/cMo Kα
a = 15.9912 (8) ŵ = 10.67 mm−1
b = 8.7769 (5) ÅT = 295 (2) K
c = 14.3189 (9) Å0.20 × 0.20 × 0.10 mm
β = 109.760 (1)º
Data collection top
Bruker APEX area-detector
diffractometer		3316 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2809 reflections with I > 2σ(I)
Tmin = 0.096, Tmax = 0.415Rint = 0.036
11857 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031130 restraints
wR(F2) = 0.081H-atom parameters constrained
S = 1.01Δρmax = 0.77 e Å−3
3316 reflectionsΔρmin = −0.84 e Å−3
210 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Hg10.254133 (15)0.47282 (3)0.529270 (15)0.05327 (11)
Br10.180 (3)0.253 (4)0.411 (2)0.0635 (18)0.218 (2)
Br20.415 (3)0.435 (4)0.623 (3)0.0563 (12)0.136 (2)
Br30.2771 (14)0.660 (2)0.4126 (18)0.0577 (7)0.090 (2)
Br40.1650 (4)0.5446 (5)0.6389 (4)0.0643 (7)0.556 (2)
Cl10.1756 (17)0.251 (3)0.4255 (15)0.0635 (18)0.782 (2)
Cl20.4166 (11)0.4121 (14)0.6159 (11)0.0563 (12)0.864 (2)
Cl30.2607 (3)0.6920 (5)0.4159 (4)0.0577 (7)0.910 (2)
Cl40.1718 (14)0.5153 (17)0.6513 (14)0.0643 (7)0.444 (2)
N10.5444 (6)0.0632 (18)0.3892 (8)0.0415 (18)0.50
C10.5126 (7)0.2014 (16)0.4108 (11)0.049 (2)0.50
H10.55170.28200.43560.059*0.50
C20.4226 (8)0.2193 (12)0.3955 (13)0.047 (3)0.50
H20.40140.31180.41000.057*0.50
C30.3643 (6)0.0990 (12)0.3585 (9)0.045 (3)0.50
H30.30410.11090.34820.054*0.50
C40.3960 (8)−0.0393 (12)0.3368 (10)0.047 (3)0.50
H40.3570−0.11980.31210.056*0.50
C50.4861 (8)−0.0572 (14)0.3522 (10)0.045 (2)0.50
H50.5073−0.14970.33770.054*0.50
N20.8831 (4)−0.0935 (9)0.3268 (6)0.051 (2)0.50
C60.9378 (8)−0.1770 (12)0.4066 (7)0.071 (2)0.50
H60.9134−0.22920.44790.085*0.50
C71.0288 (7)−0.1824 (17)0.4249 (8)0.056 (2)0.50
H71.0654−0.23820.47830.067*0.50
C81.0651 (4)−0.1044 (18)0.3632 (10)0.058 (3)0.50
H81.1260−0.10800.37540.070*0.50
C91.0104 (7)−0.0209 (15)0.2834 (9)0.074 (2)0.50
H91.03480.03130.24210.089*0.50
C100.9194 (7)−0.0155 (10)0.2651 (6)0.058 (3)0.50
H100.88280.04030.21170.070*0.50
C110.6368 (10)0.020 (4)0.4005 (15)0.055 (3)0.50
H11A0.67580.05250.46540.066*0.50
H11B0.6407−0.08970.39710.066*0.50
C120.6673 (6)0.0893 (13)0.3235 (9)0.060 (3)0.50
H12A0.65490.19770.31970.072*0.50
H12B0.63470.04470.25950.072*0.50
C130.7646 (6)0.0649 (11)0.3455 (9)0.065 (2)0.50
H13A0.79450.06790.41670.078*0.50
H13B0.78790.14730.31640.078*0.50
C140.7849 (5)−0.0846 (11)0.3060 (8)0.058 (2)0.50
H14A0.7659−0.16850.33810.069*0.50
H14B0.7535−0.09110.23520.069*0.50
N1'0.5395 (6)0.0366 (18)0.3852 (8)0.0415 (18)0.50
C1'0.5296 (7)0.1906 (17)0.4015 (11)0.049 (2)0.50
H1'0.57850.25530.41710.059*0.50
C2'0.4467 (8)0.2480 (12)0.3944 (13)0.047 (3)0.50
H2'0.44010.35110.40530.057*0.50
C3'0.3737 (6)0.1514 (12)0.3711 (10)0.045 (3)0.50
H3'0.31820.18980.36640.054*0.50
C4'0.3835 (7)−0.0027 (12)0.3549 (10)0.047 (3)0.50
H4'0.3346−0.06730.33930.056*0.50
C5'0.4664 (8)−0.0601 (13)0.3619 (10)0.045 (2)0.50
H5'0.4730−0.16320.35100.054*0.50
N2'0.8955 (4)−0.0307 (10)0.3618 (6)0.051 (2)0.50
C6'0.9442 (8)−0.1532 (12)0.4144 (7)0.071 (2)0.50
H6'0.9242−0.20620.45900.085*0.50
C7'1.0227 (8)−0.1965 (15)0.4003 (9)0.056 (2)0.50
H7'1.0552−0.27850.43550.067*0.50
C8'1.0525 (5)−0.1173 (17)0.3336 (10)0.058 (3)0.50
H8'1.1051−0.14630.32420.070*0.50
C9'1.0039 (8)0.0051 (14)0.2810 (9)0.074 (2)0.50
H9'1.02390.05810.23630.089*0.50
C10'0.9254 (7)0.0485 (10)0.2951 (7)0.058 (3)0.50
H10'0.89290.13040.25980.070*0.50
C11'0.6329 (11)−0.004 (4)0.3962 (13)0.055 (3)0.50
H11C0.67350.06140.44560.066*0.50
H11D0.6447−0.10860.41860.066*0.50
C12'0.6475 (5)0.0143 (14)0.2997 (8)0.060 (3)0.50
H12C0.64700.12190.28400.072*0.50
H12D0.5991−0.03410.24790.072*0.50
C13'0.7332 (5)−0.0535 (14)0.3013 (8)0.065 (2)0.50
H13C0.7332−0.16140.31610.078*0.50
H13D0.7383−0.04350.23590.078*0.50
C14'0.8112 (5)0.0193 (12)0.3753 (8)0.058 (2)0.50
H14C0.8126−0.00730.44160.069*0.50
H14D0.80580.12910.36840.069*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.05137 (18)0.04907 (17)0.06456 (16)−0.00278 (9)0.02638 (13)−0.00031 (10)
Br10.068 (3)0.0608 (8)0.076 (5)−0.0161 (14)0.043 (3)−0.018 (3)
Br20.0542 (9)0.047 (4)0.061 (2)0.011 (3)0.0108 (12)−0.007 (2)
Br30.047 (2)0.055 (2)0.0626 (8)−0.0058 (11)0.0074 (12)0.0138 (13)
Br40.0685 (12)0.0632 (19)0.0745 (16)0.0078 (13)0.0418 (12)0.0016 (11)
Cl10.068 (3)0.0608 (8)0.076 (5)−0.0161 (14)0.043 (3)−0.018 (3)
Cl20.0542 (9)0.047 (4)0.061 (2)0.011 (3)0.0108 (12)−0.007 (2)
Cl30.047 (2)0.055 (2)0.0626 (8)−0.0058 (11)0.0074 (12)0.0138 (13)
Cl40.0685 (12)0.0632 (19)0.0745 (16)0.0078 (13)0.0418 (12)0.0016 (11)
N10.034 (3)0.041 (5)0.047 (2)−0.001 (2)0.011 (2)−0.004 (2)
C10.039 (5)0.057 (4)0.058 (4)0.012 (4)0.024 (3)−0.008 (3)
C20.032 (6)0.052 (5)0.064 (3)0.006 (4)0.023 (5)0.005 (4)
C30.040 (4)0.047 (8)0.050 (4)0.006 (4)0.019 (3)−0.003 (5)
C40.035 (4)0.062 (6)0.058 (5)0.005 (4)0.036 (4)−0.001 (4)
C50.027 (5)0.057 (4)0.061 (4)0.003 (3)0.028 (4)0.012 (3)
N20.023 (3)0.063 (7)0.058 (6)−0.016 (4)0.003 (4)−0.006 (4)
C60.056 (4)0.074 (5)0.079 (4)0.006 (4)0.019 (3)0.020 (4)
C70.045 (4)0.052 (4)0.057 (6)0.003 (3)−0.002 (4)−0.014 (4)
C80.037 (4)0.076 (5)0.057 (8)−0.005 (4)0.011 (4)−0.018 (5)
C90.052 (4)0.088 (6)0.089 (4)−0.001 (4)0.033 (4)0.020 (4)
C100.046 (4)0.070 (7)0.060 (6)0.003 (5)0.021 (4)0.008 (5)
C110.039 (3)0.059 (7)0.063 (3)0.004 (3)0.011 (3)−0.004 (4)
C120.043 (5)0.070 (7)0.066 (5)−0.003 (5)0.018 (4)0.003 (5)
C130.057 (5)0.072 (5)0.069 (5)0.002 (4)0.025 (5)−0.008 (4)
C140.044 (5)0.064 (5)0.064 (4)−0.003 (4)0.017 (4)0.000 (4)
N1'0.034 (3)0.041 (5)0.047 (2)−0.001 (2)0.011 (2)−0.004 (2)
C1'0.039 (5)0.057 (4)0.058 (4)0.012 (4)0.024 (3)−0.008 (3)
C2'0.032 (6)0.052 (5)0.064 (3)0.006 (4)0.023 (5)0.005 (4)
C3'0.040 (4)0.047 (8)0.050 (4)0.006 (4)0.019 (3)−0.003 (5)
C4'0.035 (4)0.062 (6)0.058 (5)0.005 (4)0.036 (4)−0.001 (4)
C5'0.027 (5)0.057 (4)0.061 (4)0.003 (3)0.028 (4)0.012 (3)
N2'0.023 (3)0.063 (7)0.058 (6)−0.016 (4)0.003 (4)−0.006 (4)
C6'0.056 (4)0.074 (5)0.079 (4)0.006 (4)0.019 (3)0.020 (4)
C7'0.045 (4)0.052 (4)0.057 (6)0.003 (3)−0.002 (4)−0.014 (4)
C8'0.037 (4)0.076 (5)0.057 (8)−0.005 (4)0.011 (4)−0.018 (5)
C9'0.052 (4)0.088 (6)0.089 (4)−0.001 (4)0.033 (4)0.020 (4)
C10'0.046 (4)0.070 (7)0.060 (6)0.003 (5)0.021 (4)0.008 (5)
C11'0.039 (3)0.059 (7)0.063 (3)0.004 (3)0.011 (3)−0.004 (4)
C12'0.043 (5)0.070 (7)0.066 (5)−0.003 (5)0.018 (4)0.003 (5)
C13'0.057 (5)0.072 (5)0.069 (5)0.002 (4)0.025 (5)−0.008 (4)
C14'0.044 (5)0.064 (5)0.064 (4)−0.003 (4)0.017 (4)0.000 (4)
Geometric parameters (Å, °) top
Hg1—Cl12.51 (2)C13—H13A0.97
Hg1—Br12.58 (4)C13—H13B0.97
Hg1—Cl22.529 (15)C14—H14A0.97
Hg1—Br22.49 (4)C14—H14B0.97
Hg1—Cl32.543 (5)N1'—C1'1.39
Hg1—Br32.46 (2)N1'—C5'1.39
Hg1—Cl42.545 (18)N1'—C11'1.491 (8)
Hg1—Br42.530 (5)C1'—C2'1.39
N1—C11.39C1'—H1'0.93
N1—C51.39C2'—C3'1.39
N1—C111.479 (8)C2'—H2'0.93
C1—C21.39C3'—C4'1.39
C1—H10.93C3'—H3'0.93
C2—C31.39C4'—C5'1.39
C2—H20.93C4'—H4'0.93
C3—C41.39C5'—H5'0.93
C3—H30.93N2'—C6'1.39
C4—C51.39N2'—C10'1.39
C4—H40.93N2'—C14'1.492 (8)
C5—H50.93C6'—C7'1.39
N2—C61.39C6'—H6'0.93
N2—C101.39C7'—C8'1.39
N2—C141.498 (8)C7'—H7'0.93
C6—C71.39C8'—C9'1.39
C6—H60.93C8'—H8'0.93
C7—C81.39C9'—C10'1.39
C7—H70.93C9'—H9'0.93
C8—C91.39C10'—H10'0.93
C8—H80.93C11'—C12'1.486 (9)
C9—C101.39C11'—H11C0.97
C9—H90.93C11'—H11D0.97
C10—H100.93C12'—C13'1.487 (8)
C11—C121.478 (9)C12'—H12C0.97
C11—H11A0.97C12'—H12D0.97
C11—H11B0.97C13'—C14'1.481 (8)
C12—C131.494 (8)C13'—H13C0.97
C12—H12A0.97C13'—H13D0.97
C12—H12B0.97C14'—H14C0.97
C13—C141.506 (8)C14'—H14D0.97
Cl2—Hg1—Br25.1 (9)C13—C12—H12B109.3
Cl2—Hg1—Cl3102.4 (4)H12A—C12—H12B108.0
Br2—Hg1—Cl3100.6 (11)C12—C13—C14112.8 (7)
Cl2—Hg1—Br396.3 (6)C12—C13—H13A109.0
Br2—Hg1—Br395.1 (12)C14—C13—H13A109.0
Cl3—Hg1—Br38.9 (4)C12—C13—H13B109.0
Cl2—Hg1—Cl4112.2 (6)C14—C13—H13B109.0
Br2—Hg1—Cl4109.4 (10)H13A—C13—H13B107.8
Cl3—Hg1—Cl4118.0 (3)N2—C14—C13108.4 (6)
Br3—Hg1—Cl4126.8 (5)N2—C14—H14A110.0
Cl2—Hg1—Br4116.7 (3)C13—C14—H14A110.0
Br2—Hg1—Br4113.4 (9)N2—C14—H14B110.0
Cl3—Hg1—Br4111.18 (10)C13—C14—H14B110.0
Br3—Hg1—Br4120.0 (4)H14A—C14—H14B108.4
Cl4—Hg1—Br47.0 (4)C1'—N1'—C5'120.0
Cl2—Hg1—Cl1110.7 (7)C1'—N1'—C11'112.4 (16)
Br2—Hg1—Cl1115.8 (9)C5'—N1'—C11'127.6 (16)
Cl3—Hg1—Cl1109.2 (5)C2'—C1'—N1'120.0
Br3—Hg1—Cl1106.0 (7)C2'—C1'—H1'120.0
Cl4—Hg1—Cl1104.4 (6)N1'—C1'—H1'120.0
Br4—Hg1—Cl1106.6 (5)C1'—C2'—C3'120.0
Cl2—Hg1—Br1109.3 (9)C1'—C2'—H2'120.0
Br2—Hg1—Br1114.4 (11)C3'—C2'—H2'120.0
Cl3—Hg1—Br1104.8 (8)C4'—C3'—C2'120.0
Br3—Hg1—Br1101.2 (9)C4'—C3'—H3'120.0
Cl4—Hg1—Br1109.5 (8)C2'—C3'—H3'120.0
Br4—Hg1—Br1111.5 (7)C3'—C4'—C5'120.0
Cl1—Hg1—Br15.4 (10)C3'—C4'—H4'120.0
C1—N1—C5120.0C5'—C4'—H4'120.0
C1—N1—C11128.6 (16)C4'—C5'—N1'120.0
C5—N1—C11111.4 (16)C4'—C5'—H5'120.0
C2—C1—N1120.0N1'—C5'—H5'120.0
C2—C1—H1120.0C6'—N2'—C10'120.0
N1—C1—H1120.0C6'—N2'—C14'121.5 (8)
C1—C2—C3120.0C10'—N2'—C14'118.5 (8)
C1—C2—H2120.0N2'—C6'—C7'120.0
C3—C2—H2120.0N2'—C6'—H6'120.0
C4—C3—C2120.0C7'—C6'—H6'120.0
C4—C3—H3120.0C8'—C7'—C6'120.0
C2—C3—H3120.0C8'—C7'—H7'120.0
C5—C4—C3120.0C6'—C7'—H7'120.0
C5—C4—H4120.0C7'—C8'—C9'120.0
C3—C4—H4120.0C7'—C8'—H8'120.0
C4—C5—N1120.0C9'—C8'—H8'120.0
C4—C5—H5120.0C10'—C9'—C8'120.0
N1—C5—H5120.0C10'—C9'—H9'120.0
C6—N2—C10120.0C8'—C9'—H9'120.0
C6—N2—C14121.1 (8)C9'—C10'—N2'120.0
C10—N2—C14118.9 (8)C9'—C10'—H10'120.0
N2—C6—C7120.0N2'—C10'—H10'120.0
N2—C6—H6120.0C12'—C11'—N1'110.0 (7)
C7—C6—H6120.0C12'—C11'—H11C109.7
C8—C7—C6120.0N1'—C11'—H11C109.7
C8—C7—H7120.0C12'—C11'—H11D109.7
C6—C7—H7120.0N1'—C11'—H11D109.7
C9—C8—C7120.0H11C—C11'—H11D108.2
C9—C8—H8120.0C11'—C12'—C13'112.1 (8)
C7—C8—H8120.0C11'—C12'—H12C109.2
C8—C9—C10120.0C13'—C12'—H12C109.2
C8—C9—H9120.0C11'—C12'—H12D109.2
C10—C9—H9120.0C13'—C12'—H12D109.2
C9—C10—N2120.0H12C—C12'—H12D107.9
C9—C10—H10120.0C14'—C13'—C12'112.8 (7)
N2—C10—H10120.0C14'—C13'—H13C109.0
C12—C11—N1112.6 (8)C12'—C13'—H13C109.0
C12—C11—H11A109.1C14'—C13'—H13D109.0
N1—C11—H11A109.1C12'—C13'—H13D109.0
C12—C11—H11B109.1H13C—C13'—H13D107.8
N1—C11—H11B109.1C13'—C14'—N2'111.1 (6)
H11A—C11—H11B107.8C13'—C14'—H14C109.4
C11—C12—C13111.5 (8)N2'—C14'—H14C109.4
C11—C12—H12A109.3C13'—C14'—H14D109.4
C13—C12—H12A109.3N2'—C14'—H14D109.4
C11—C12—H12B109.3H14C—C14'—H14D108.0
C11—N1—C1—C2−179.6 (3)C11'—N1'—C1'—C2'−179.8 (2)
C11—N1—C5—C4179.7 (2)C11'—N1'—C5'—C4'179.8 (3)
C14—N2—C6—C7−179.4 (3)C14'—N2'—C6'—C7'−179.8 (3)
C14—N2—C10—C9179.4 (3)C14'—N2'—C10'—C9'179.8 (3)
C1—N1—C11—C12−74 (2)C1'—N1'—C11'—C12'−89 (2)
C5—N1—C11—C12106 (2)C5'—N1'—C11'—C12'91 (2)
N1—C11—C12—C13171.0 (16)N1'—C11'—C12'—C13'−168.6 (16)
C11—C12—C13—C1486.6 (17)C11'—C12'—C13'—C14'−61.7 (19)
C6—N2—C14—C13100.1 (10)C12'—C13'—C14'—N2'−169.3 (9)
C10—N2—C14—C13−79.3 (10)C6'—N2'—C14'—C13'−93.4 (11)
C12—C13—C14—N2176.8 (9)C10'—N2'—C14'—C13'86.8 (11)
Selected geometric parameters (Å) top
Hg1—Cl12.51 (2)Hg1—Cl32.543 (5)
Hg1—Br12.58 (4)Hg1—Br32.46 (2)
Hg1—Cl22.529 (15)Hg1—Cl42.545 (18)
Hg1—Br22.49 (4)Hg1—Br42.530 (5)
Acknowledgements top

The authors thank the National Natural Science Foundation of China (grant No. 20671083), the Henan Province Excellent Young Foundation (grant No. 0612002800), Zhengzhou University and the University of Malaya for supporting this work. We thank Central China Normal University for the diffraction measurements.

references
References top

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Westrip, S. P. (2007). publCIF. In preparation.