Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702747X/ci2389sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702747X/ci2389Isup2.hkl |
CCDC reference: 654757
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 diiodide (0.091 g, 0.2 mmol) in DMF (10 ml). The mixture was set aside for the formation of colorless crystals in 30% yield after several days.
The four halogen atoms lie in general positions. Initial attempts to refine the structure with either four iodines or four bromines gave unacceptably high R-indices and large peaks/deep holes. The four halogen atoms were then refined as four (I+Br) mixtures; one attempt had the mixtures to have the same displacement parameters as well as sharing the same sites. A second attempt allowed the components having the same displacement parameters only. The second led to a formulation consisting of approximately two I and two Br atoms. The use of a restraint that fixed the number of I and Br atoms as exactly two I and two Br led to occupancies of 0.824 (2), 0.614 (2), 0.325 (2) and 0.237 (2), respectively, for I1, I2, I3 and I4, and 0.176 (2), 0.386 (2), 0.675 (2) and 0.763 (2), respectively, for Br1, Br2, Br3 and Br4.
The formulation is in fair agreement with CH&N elemental analysis, and furthermore, there were neither large peaks nor deep holes in the difference Fourier map; the final difference Fourier map had a large peak at 0.77 Å from Hg1. 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 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).
The preceding study reports the structure of 1,2-butanedipyridinium bromotrichloromercurate(II) (Niu et al., 2007). Replacing the mercuric dichloride reactant by mercuric diiodide furnishes a similar tetrahalogenomercurate. The anion of the salt is composed two bromines and two chlorines that are disordered (Fig. 1); the metal atom shows tetrahedral coordination. Selected bond distances are given in Table 1.
For the related butanedipyridinium bromidotrichloridomercurate, see: Niu et al. (2007).
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).
(C14H18N2)[HgBr2I2] | F(000) = 2976 |
Mr = 828.51 | Dx = 2.598 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5589 reflections |
a = 16.0181 (8) Å | θ = 2.4–22.3° |
b = 15.3290 (7) Å | µ = 13.95 mm−1 |
c = 17.2550 (8) Å | T = 295 K |
V = 4236.8 (3) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.20 × 0.20 mm |
Bruker APEX area-detector diffractometer | 3722 independent reflections |
Radiation source: fine-focus sealed tube | 2713 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.059, Tmax = 0.165 | k = −18→18 |
31877 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0448P)2 + 2.7056P] where P = (Fo2 + 2Fc2)/3 |
3722 reflections | (Δ/σ)max = 0.001 |
198 parameters | Δρmax = 1.03 e Å−3 |
226 restraints | Δρmin = −0.51 e Å−3 |
(C14H18N2)[HgBr2I2] | V = 4236.8 (3) Å3 |
Mr = 828.51 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 16.0181 (8) Å | µ = 13.95 mm−1 |
b = 15.3290 (7) Å | T = 295 K |
c = 17.2550 (8) Å | 0.20 × 0.20 × 0.20 mm |
Bruker APEX area-detector diffractometer | 3722 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2713 reflections with I > 2σ(I) |
Tmin = 0.059, Tmax = 0.165 | Rint = 0.054 |
31877 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 226 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.01 | Δρmax = 1.03 e Å−3 |
3722 reflections | Δρmin = −0.51 e Å−3 |
198 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Hg1 | 0.59858 (2) | 0.751573 (19) | 0.866623 (17) | 0.05914 (13) | |
I1 | 0.68911 (13) | 0.67185 (13) | 0.75380 (15) | 0.0712 (4) | 0.824 (2) |
I2 | 0.5676 (4) | 0.9215 (4) | 0.8189 (3) | 0.0717 (8) | 0.614 (2) |
I3 | 0.677 (4) | 0.744 (4) | 1.007 (3) | 0.0732 (18) | 0.325 (2) |
I4 | 0.4457 (13) | 0.6720 (11) | 0.8836 (11) | 0.0691 (8) | 0.237 (2) |
Br1 | 0.6735 (11) | 0.6560 (12) | 0.7524 (12) | 0.0712 (4) | 0.176 (2) |
Br2 | 0.5830 (10) | 0.9228 (10) | 0.8330 (7) | 0.0717 (8) | 0.386 (2) |
Br3 | 0.674 (3) | 0.743 (3) | 1.000 (2) | 0.0732 (18) | 0.675 (2) |
Br4 | 0.4489 (6) | 0.6863 (4) | 0.8958 (5) | 0.0691 (8) | 0.763 (2) |
N1 | 0.6643 (7) | 0.4418 (11) | 0.5603 (7) | 0.0511 (19) | 0.50 |
C1 | 0.7070 (9) | 0.5169 (11) | 0.5387 (7) | 0.062 (3) | 0.50 |
H1 | 0.6879 | 0.5504 | 0.4974 | 0.074* | 0.50 |
C2 | 0.7784 (8) | 0.5420 (10) | 0.5788 (10) | 0.065 (4) | 0.50 |
H2 | 0.8070 | 0.5922 | 0.5643 | 0.078* | 0.50 |
C3 | 0.8070 (8) | 0.4919 (12) | 0.6405 (9) | 0.065 (3) | 0.50 |
H3 | 0.8547 | 0.5087 | 0.6673 | 0.078* | 0.50 |
C4 | 0.7643 (12) | 0.4168 (12) | 0.6621 (9) | 0.071 (3) | 0.50 |
H4 | 0.7835 | 0.3833 | 0.7034 | 0.085* | 0.50 |
C5 | 0.6930 (11) | 0.3918 (10) | 0.6220 (9) | 0.065 (3) | 0.50 |
H5 | 0.6644 | 0.3415 | 0.6364 | 0.077* | 0.50 |
N2 | 0.5665 (12) | 0.1988 (7) | 0.3523 (6) | 0.064 (3) | 0.50 |
C6 | 0.6475 (11) | 0.1667 (10) | 0.3470 (13) | 0.082 (4) | 0.50 |
H6 | 0.6907 | 0.2033 | 0.3317 | 0.098* | 0.50 |
C7 | 0.6638 (9) | 0.0798 (11) | 0.3645 (15) | 0.105 (4) | 0.50 |
H7 | 0.7179 | 0.0583 | 0.3609 | 0.126* | 0.50 |
C8 | 0.5991 (11) | 0.0251 (7) | 0.3874 (11) | 0.088 (4) | 0.50 |
H8 | 0.6100 | −0.0330 | 0.3991 | 0.105* | 0.50 |
C9 | 0.5182 (10) | 0.0572 (9) | 0.3927 (11) | 0.084 (4) | 0.50 |
H9 | 0.4749 | 0.0205 | 0.4080 | 0.101* | 0.50 |
C10 | 0.5019 (9) | 0.1440 (10) | 0.3752 (10) | 0.075 (3) | 0.50 |
H10 | 0.4477 | 0.1655 | 0.3788 | 0.090* | 0.50 |
C11 | 0.5890 (10) | 0.4165 (18) | 0.5171 (11) | 0.059 (3) | 0.50 |
H11A | 0.5599 | 0.4687 | 0.5005 | 0.071* | 0.50 |
H11B | 0.5521 | 0.3844 | 0.5514 | 0.071* | 0.50 |
C12 | 0.6080 (10) | 0.361 (2) | 0.4477 (13) | 0.055 (3) | 0.50 |
H12A | 0.6348 | 0.3076 | 0.4638 | 0.066* | 0.50 |
H12B | 0.6456 | 0.3923 | 0.4133 | 0.066* | 0.50 |
C13 | 0.5274 (9) | 0.3414 (10) | 0.4065 (8) | 0.063 (4) | 0.50 |
H13A | 0.4909 | 0.3094 | 0.4412 | 0.076* | 0.50 |
H13B | 0.4999 | 0.3957 | 0.3931 | 0.076* | 0.50 |
C14 | 0.5405 (11) | 0.2897 (8) | 0.3354 (7) | 0.063 (4) | 0.50 |
H14A | 0.5829 | 0.3176 | 0.3039 | 0.075* | 0.50 |
H14B | 0.4891 | 0.2887 | 0.3057 | 0.075* | 0.50 |
N1' | 0.6530 (7) | 0.4378 (11) | 0.5467 (7) | 0.0511 (19) | 0.50 |
C1' | 0.6846 (9) | 0.5220 (10) | 0.5408 (8) | 0.062 (3) | 0.50 |
H1' | 0.6626 | 0.5605 | 0.5045 | 0.074* | 0.50 |
C2' | 0.7490 (8) | 0.5488 (9) | 0.5893 (10) | 0.065 (4) | 0.50 |
H2' | 0.7701 | 0.6051 | 0.5854 | 0.078* | 0.50 |
C3' | 0.7818 (8) | 0.4913 (12) | 0.6437 (9) | 0.065 (3) | 0.50 |
H3' | 0.8249 | 0.5092 | 0.6761 | 0.078* | 0.50 |
C4' | 0.7502 (12) | 0.4071 (11) | 0.6495 (9) | 0.071 (3) | 0.50 |
H4' | 0.7722 | 0.3686 | 0.6859 | 0.085* | 0.50 |
C5' | 0.6859 (11) | 0.3803 (9) | 0.6010 (9) | 0.065 (3) | 0.50 |
H5' | 0.6647 | 0.3240 | 0.6049 | 0.077* | 0.50 |
N2' | 0.5766 (12) | 0.1750 (6) | 0.3511 (6) | 0.064 (3) | 0.50 |
C6' | 0.6585 (11) | 0.1463 (10) | 0.3439 (12) | 0.082 (4) | 0.50 |
H6' | 0.6984 | 0.1821 | 0.3212 | 0.098* | 0.50 |
C7' | 0.6807 (9) | 0.0640 (11) | 0.3706 (15) | 0.105 (4) | 0.50 |
H7' | 0.7355 | 0.0447 | 0.3658 | 0.126* | 0.50 |
C8' | 0.6210 (11) | 0.0104 (8) | 0.4046 (11) | 0.088 (4) | 0.50 |
H8' | 0.6359 | −0.0447 | 0.4225 | 0.105* | 0.50 |
C9' | 0.5391 (10) | 0.0391 (9) | 0.4118 (10) | 0.084 (4) | 0.50 |
H9' | 0.4992 | 0.0033 | 0.4345 | 0.101* | 0.50 |
C10' | 0.5169 (9) | 0.1215 (10) | 0.3851 (10) | 0.075 (3) | 0.50 |
H10' | 0.4620 | 0.1407 | 0.3899 | 0.090* | 0.50 |
C11' | 0.5849 (10) | 0.4077 (18) | 0.4962 (11) | 0.059 (3) | 0.50 |
H11C | 0.5580 | 0.4580 | 0.4730 | 0.071* | 0.50 |
H11D | 0.5437 | 0.3776 | 0.5275 | 0.071* | 0.50 |
C12' | 0.6136 (11) | 0.3480 (19) | 0.4332 (13) | 0.055 (3) | 0.50 |
H12C | 0.6360 | 0.2948 | 0.4553 | 0.066* | 0.50 |
H12D | 0.6572 | 0.3759 | 0.4031 | 0.066* | 0.50 |
C13' | 0.5401 (10) | 0.3271 (9) | 0.3818 (9) | 0.063 (4) | 0.50 |
H13C | 0.4954 | 0.3030 | 0.4132 | 0.076* | 0.50 |
H13D | 0.5198 | 0.3804 | 0.3582 | 0.076* | 0.50 |
C14' | 0.5622 (11) | 0.2640 (8) | 0.3201 (7) | 0.063 (4) | 0.50 |
H14C | 0.6122 | 0.2838 | 0.2939 | 0.075* | 0.50 |
H14D | 0.5174 | 0.2620 | 0.2823 | 0.075* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.0614 (2) | 0.0609 (2) | 0.0551 (2) | 0.00344 (15) | 0.00333 (15) | −0.00355 (15) |
I1 | 0.0754 (10) | 0.0702 (10) | 0.0680 (4) | −0.0013 (5) | 0.0145 (7) | −0.0171 (6) |
I2 | 0.104 (2) | 0.0568 (4) | 0.0548 (18) | 0.0035 (12) | 0.0093 (11) | −0.0019 (12) |
I3 | 0.070 (2) | 0.0910 (6) | 0.058 (5) | 0.0138 (12) | −0.011 (3) | −0.002 (3) |
I4 | 0.0619 (9) | 0.055 (2) | 0.090 (3) | −0.0031 (15) | 0.0052 (15) | −0.0088 (13) |
Br1 | 0.0754 (10) | 0.0702 (10) | 0.0680 (4) | −0.0013 (5) | 0.0145 (7) | −0.0171 (6) |
Br2 | 0.104 (2) | 0.0568 (4) | 0.0548 (18) | 0.0035 (12) | 0.0093 (11) | −0.0019 (12) |
Br3 | 0.070 (2) | 0.0910 (6) | 0.058 (5) | 0.0138 (12) | −0.011 (3) | −0.002 (3) |
Br4 | 0.0619 (9) | 0.055 (2) | 0.090 (3) | −0.0031 (15) | 0.0052 (15) | −0.0088 (13) |
N1 | 0.053 (4) | 0.054 (3) | 0.047 (4) | 0.008 (3) | 0.003 (3) | 0.001 (3) |
C1 | 0.059 (6) | 0.055 (4) | 0.072 (5) | 0.007 (5) | 0.004 (5) | 0.004 (4) |
C2 | 0.066 (7) | 0.066 (5) | 0.063 (5) | −0.005 (5) | 0.015 (6) | −0.007 (4) |
C3 | 0.059 (6) | 0.071 (5) | 0.064 (5) | 0.003 (5) | 0.002 (5) | −0.013 (4) |
C4 | 0.080 (6) | 0.070 (5) | 0.063 (5) | 0.004 (5) | −0.011 (5) | −0.001 (4) |
C5 | 0.079 (5) | 0.056 (5) | 0.059 (7) | 0.004 (4) | 0.006 (5) | −0.002 (5) |
N2 | 0.069 (5) | 0.069 (6) | 0.054 (4) | −0.015 (5) | −0.008 (4) | −0.004 (4) |
C6 | 0.078 (6) | 0.087 (7) | 0.081 (5) | −0.013 (5) | 0.011 (5) | −0.005 (5) |
C7 | 0.103 (7) | 0.106 (7) | 0.106 (6) | 0.008 (5) | 0.007 (5) | −0.010 (5) |
C8 | 0.097 (7) | 0.078 (6) | 0.088 (7) | 0.002 (5) | −0.016 (6) | 0.000 (5) |
C9 | 0.087 (7) | 0.080 (6) | 0.086 (7) | −0.013 (5) | −0.010 (5) | 0.004 (5) |
C10 | 0.068 (6) | 0.074 (6) | 0.082 (6) | −0.005 (5) | −0.002 (5) | −0.001 (5) |
C11 | 0.052 (4) | 0.067 (5) | 0.058 (7) | 0.001 (4) | 0.002 (4) | −0.003 (5) |
C12 | 0.054 (4) | 0.055 (6) | 0.055 (6) | 0.001 (4) | 0.003 (4) | 0.001 (4) |
C13 | 0.064 (5) | 0.062 (5) | 0.064 (7) | −0.002 (4) | −0.001 (5) | −0.003 (5) |
C14 | 0.064 (6) | 0.065 (6) | 0.058 (5) | 0.009 (5) | −0.011 (5) | 0.001 (5) |
N1' | 0.053 (4) | 0.054 (3) | 0.047 (4) | 0.008 (3) | 0.003 (3) | 0.001 (3) |
C1' | 0.059 (6) | 0.055 (4) | 0.072 (5) | 0.007 (5) | 0.004 (5) | 0.004 (4) |
C2' | 0.066 (7) | 0.066 (5) | 0.063 (5) | −0.005 (5) | 0.015 (6) | −0.007 (4) |
C3' | 0.059 (6) | 0.071 (5) | 0.064 (5) | 0.003 (5) | 0.002 (5) | −0.013 (4) |
C4' | 0.080 (6) | 0.070 (5) | 0.063 (5) | 0.004 (5) | −0.011 (5) | −0.001 (4) |
C5' | 0.079 (5) | 0.056 (5) | 0.059 (7) | 0.004 (4) | 0.006 (5) | −0.002 (5) |
N2' | 0.069 (5) | 0.069 (6) | 0.054 (4) | −0.015 (5) | −0.008 (4) | −0.004 (4) |
C6' | 0.078 (6) | 0.087 (7) | 0.081 (5) | −0.013 (5) | 0.011 (5) | −0.005 (5) |
C7' | 0.103 (7) | 0.106 (7) | 0.106 (6) | 0.008 (5) | 0.007 (5) | −0.010 (5) |
C8' | 0.097 (7) | 0.078 (6) | 0.088 (7) | 0.002 (5) | −0.016 (6) | 0.000 (5) |
C9' | 0.087 (7) | 0.080 (6) | 0.086 (7) | −0.013 (5) | −0.010 (5) | 0.004 (5) |
C10' | 0.068 (6) | 0.074 (6) | 0.082 (6) | −0.005 (5) | −0.002 (5) | −0.001 (5) |
C11' | 0.052 (4) | 0.067 (5) | 0.058 (7) | 0.001 (4) | 0.002 (4) | −0.003 (5) |
C12' | 0.054 (4) | 0.055 (6) | 0.055 (6) | 0.001 (4) | 0.003 (4) | 0.001 (4) |
C13' | 0.064 (5) | 0.062 (5) | 0.064 (7) | −0.002 (4) | −0.001 (5) | −0.003 (5) |
C14' | 0.064 (6) | 0.065 (6) | 0.058 (5) | 0.009 (5) | −0.011 (5) | 0.001 (5) |
Hg1—Br1 | 2.73 (2) | C13—H13A | 0.97 |
Hg1—Br2 | 2.70 (2) | C13—H13B | 0.97 |
Hg1—Br3 | 2.61 (4) | C14—H14A | 0.97 |
Hg1—Br4 | 2.646 (9) | C14—H14B | 0.97 |
Hg1—I1 | 2.718 (2) | N1'—C1' | 1.39 |
Hg1—I2 | 2.777 (6) | N1'—C5' | 1.39 |
Hg1—I3 | 2.72 (5) | N1'—C11' | 1.470 (8) |
Hg1—I4 | 2.75 (2) | C1'—C2' | 1.39 |
N1—C1 | 1.39 | C1'—H1' | 0.93 |
N1—C5 | 1.39 | C2'—C3' | 1.39 |
N1—C11 | 1.470 (8) | C2'—H2' | 0.93 |
C1—C2 | 1.39 | C3'—C4' | 1.39 |
C1—H1 | 0.93 | C3'—H3' | 0.93 |
C2—C3 | 1.39 | C4'—C5' | 1.39 |
C2—H2 | 0.93 | C4'—H4' | 0.93 |
C3—C4 | 1.39 | C5'—H5' | 0.93 |
C3—H3 | 0.93 | N2'—C6' | 1.39 |
C4—C5 | 1.39 | N2'—C10' | 1.39 |
C4—H4 | 0.93 | N2'—C14' | 1.483 (9) |
C5—H5 | 0.93 | C6'—C7' | 1.39 |
N2—C6 | 1.39 | C6'—H6' | 0.93 |
N2—C10 | 1.39 | C7'—C8' | 1.39 |
N2—C14 | 1.484 (9) | C7'—H7' | 0.93 |
C6—C7 | 1.39 | C8'—C9' | 1.39 |
C6—H6 | 0.93 | C8'—H8' | 0.93 |
C7—C8 | 1.39 | C9'—C10' | 1.39 |
C7—H7 | 0.93 | C9'—H9' | 0.93 |
C8—C9 | 1.39 | C10'—H10' | 0.93 |
C8—H8 | 0.93 | C11'—C12' | 1.493 (9) |
C9—C10 | 1.39 | C11'—H11C | 0.97 |
C9—H9 | 0.93 | C11'—H11D | 0.97 |
C10—H10 | 0.93 | C12'—C13' | 1.509 (9) |
C11—C12 | 1.496 (9) | C12'—H12C | 0.97 |
C11—H11A | 0.97 | C12'—H12D | 0.97 |
C11—H11B | 0.97 | C13'—C14' | 1.481 (8) |
C12—C13 | 1.506 (9) | C13'—H13C | 0.97 |
C12—H12A | 0.97 | C13'—H13D | 0.97 |
C12—H12B | 0.97 | C14'—H14C | 0.97 |
C13—C14 | 1.475 (8) | C14'—H14D | 0.97 |
Br3—Hg1—I3 | 0 (2) | C13—C12—H12B | 110.0 |
Br3—Hg1—Br4 | 103.6 (10) | H12A—C12—H12B | 108.3 |
I3—Hg1—Br4 | 103.4 (13) | C14—C13—C12 | 112.4 (8) |
Br3—Hg1—I4 | 107.4 (11) | C14—C13—H13A | 109.1 |
I3—Hg1—I4 | 107.2 (14) | C12—C13—H13A | 109.1 |
Br4—Hg1—I4 | 6.2 (4) | C14—C13—H13B | 109.1 |
Br3—Hg1—I1 | 111.3 (10) | C12—C13—H13B | 109.1 |
I3—Hg1—I1 | 111.6 (13) | H13A—C13—H13B | 107.9 |
Br4—Hg1—I1 | 116.73 (12) | C13—C14—N2 | 112.4 (8) |
I4—Hg1—I1 | 110.6 (3) | C13—C14—H14A | 109.1 |
Br3—Hg1—Br1 | 114.1 (11) | N2—C14—H14A | 109.1 |
I3—Hg1—Br1 | 114.4 (13) | C13—C14—H14B | 109.1 |
Br4—Hg1—Br1 | 109.4 (3) | N2—C14—H14B | 109.1 |
I4—Hg1—Br1 | 103.3 (4) | H14A—C14—H14B | 107.9 |
I1—Hg1—Br1 | 7.4 (3) | C1'—N1'—C5' | 120.0 |
Br3—Hg1—I2 | 112.9 (9) | C1'—N1'—C11' | 121.2 (15) |
I3—Hg1—I2 | 112.8 (12) | C5'—N1'—C11' | 118.8 (15) |
Br4—Hg1—I2 | 104.5 (2) | N1'—C1'—C2' | 120.0 |
I4—Hg1—I2 | 106.8 (4) | N1'—C1'—H1' | 120.0 |
I1—Hg1—I2 | 107.74 (13) | C2'—C1'—H1' | 120.0 |
Br1—Hg1—I2 | 111.6 (4) | C3'—C2'—C1' | 120.0 |
Br3—Hg1—Br2 | 106.2 (10) | C3'—C2'—H2' | 120.0 |
I3—Hg1—Br2 | 106.1 (12) | C1'—C2'—H2' | 120.0 |
Br4—Hg1—Br2 | 108.9 (4) | C4'—C3'—C2' | 120.0 |
I4—Hg1—Br2 | 111.8 (5) | C4'—C3'—H3' | 120.0 |
I1—Hg1—Br2 | 109.4 (3) | C2'—C3'—H3' | 120.0 |
Br1—Hg1—Br2 | 114.0 (5) | C3'—C4'—C5' | 120.0 |
I2—Hg1—Br2 | 7.1 (3) | C3'—C4'—H4' | 120.0 |
C1—N1—C5 | 120.0 | C5'—C4'—H4' | 120.0 |
C1—N1—C11 | 119.1 (16) | C4'—C5'—N1' | 120.0 |
C5—N1—C11 | 120.9 (16) | C4'—C5'—H5' | 120.0 |
N1—C1—C2 | 120.0 | N1'—C5'—H5' | 120.0 |
N1—C1—H1 | 120.0 | C6'—N2'—C10' | 120.0 |
C2—C1—H1 | 120.0 | C6'—N2'—C14' | 114.0 (13) |
C3—C2—C1 | 120.0 | C10'—N2'—C14' | 126.0 (13) |
C3—C2—H2 | 120.0 | N2'—C6'—C7' | 120.0 |
C1—C2—H2 | 120.0 | N2'—C6'—H6' | 120.0 |
C2—C3—C4 | 120.0 | C7'—C6'—H6' | 120.0 |
C2—C3—H3 | 120.0 | C8'—C7'—C6' | 120.0 |
C4—C3—H3 | 120.0 | C8'—C7'—H7' | 120.0 |
C3—C4—C5 | 120.0 | C6'—C7'—H7' | 120.0 |
C3—C4—H4 | 120.0 | C7'—C8'—C9' | 120.0 |
C5—C4—H4 | 120.0 | C7'—C8'—H8' | 120.0 |
C4—C5—N1 | 120.0 | C9'—C8'—H8' | 120.0 |
C4—C5—H5 | 120.0 | C10'—C9'—C8' | 120.0 |
N1—C5—H5 | 120.0 | C10'—C9'—H9' | 120.0 |
C6—N2—C10 | 120.0 | C8'—C9'—H9' | 120.0 |
C6—N2—C14 | 125.6 (14) | C9'—C10'—N2' | 120.0 |
C10—N2—C14 | 114.4 (14) | C9'—C10'—H10' | 120.0 |
N2—C6—C7 | 120.0 | N2'—C10'—H10' | 120.0 |
N2—C6—H6 | 120.0 | N1'—C11'—C12' | 113.3 (8) |
C7—C6—H6 | 120.0 | N1'—C11'—H11C | 108.9 |
C6—C7—C8 | 120.0 | C12'—C11'—H11C | 108.9 |
C6—C7—H7 | 120.0 | N1'—C11'—H11D | 108.9 |
C8—C7—H7 | 120.0 | C12'—C11'—H11D | 108.9 |
C9—C8—C7 | 120.0 | H11C—C11'—H11D | 107.7 |
C9—C8—H8 | 120.0 | C11'—C12'—C13' | 108.6 (8) |
C7—C8—H8 | 120.0 | C11'—C12'—H12C | 110.0 |
C8—C9—C10 | 120.0 | C13'—C12'—H12C | 110.0 |
C8—C9—H9 | 120.0 | C11'—C12'—H12D | 110.0 |
C10—C9—H9 | 120.0 | C13'—C12'—H12D | 110.0 |
C9—C10—N2 | 120.0 | H12C—C12'—H12D | 108.4 |
C9—C10—H10 | 120.0 | C14'—C13'—C12' | 112.0 (8) |
N2—C10—H10 | 120.0 | C14'—C13'—H13C | 109.2 |
N1—C11—C12 | 112.8 (7) | C12'—C13'—H13C | 109.2 |
N1—C11—H11A | 109.0 | C14'—C13'—H13D | 109.2 |
C12—C11—H11A | 109.0 | C12'—C13'—H13D | 109.2 |
N1—C11—H11B | 109.0 | H13C—C13'—H13D | 107.9 |
C12—C11—H11B | 109.0 | C13'—C14'—N2' | 112.3 (8) |
H11A—C11—H11B | 107.8 | C13'—C14'—H14C | 109.2 |
C11—C12—C13 | 108.6 (8) | N2'—C14'—H14C | 109.2 |
C11—C12—H12A | 110.0 | C13'—C14'—H14D | 109.2 |
C13—C12—H12A | 110.0 | N2'—C14'—H14D | 109.2 |
C11—C12—H12B | 110.0 | H14C—C14'—H14D | 107.9 |
C11—N1—C1—C2 | 180.0 (3) | C11'—N1'—C1'—C2' | 180.0 (3) |
C11—N1—C5—C4 | 180.0 (3) | C11'—N1'—C5'—C4' | −180.0 (3) |
C14—N2—C6—C7 | 180.0 (3) | C14'—N2'—C6'—C7' | 180.0 (2) |
C14—N2—C10—C9 | −180.0 (2) | C14'—N2'—C10'—C9' | −180.0 (3) |
C1—N1—C11—C12 | 87 (2) | C1'—N1'—C11'—C12' | 105 (2) |
C5—N1—C11—C12 | −93 (2) | C5'—N1'—C11'—C12' | −75 (2) |
N1—C11—C12—C13 | −178 (2) | N1'—C11'—C12'—C13' | −176 (2) |
C11—C12—C13—C14 | 178 (2) | C11'—C12'—C13'—C14' | −177 (2) |
C12—C13—C14—N2 | 70 (2) | C12'—C13'—C14'—N2' | 71 (2) |
C6—N2—C14—C13 | −102.0 (14) | C6'—N2'—C14'—C13' | −113.9 (13) |
C10—N2—C14—C13 | 78.0 (14) | C10'—N2'—C14'—C13' | 66.0 (13) |
Experimental details
Crystal data | |
Chemical formula | (C14H18N2)[HgBr2I2] |
Mr | 828.51 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 295 |
a, b, c (Å) | 16.0181 (8), 15.3290 (7), 17.2550 (8) |
V (Å3) | 4236.8 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 13.95 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.059, 0.165 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31877, 3722, 2713 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.091, 1.01 |
No. of reflections | 3722 |
No. of parameters | 198 |
No. of restraints | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.03, −0.51 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
Hg1—Br1 | 2.73 (2) | Hg1—I1 | 2.718 (2) |
Hg1—Br2 | 2.70 (2) | Hg1—I2 | 2.777 (6) |
Hg1—Br3 | 2.61 (4) | Hg1—I3 | 2.72 (5) |
Hg1—Br4 | 2.646 (9) | Hg1—I4 | 2.75 (2) |
The preceding study reports the structure of 1,2-butanedipyridinium bromotrichloromercurate(II) (Niu et al., 2007). Replacing the mercuric dichloride reactant by mercuric diiodide furnishes a similar tetrahalogenomercurate. The anion of the salt is composed two bromines and two chlorines that are disordered (Fig. 1); the metal atom shows tetrahedral coordination. Selected bond distances are given in Table 1.