Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027468/ci2388sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027468/ci2388Isup2.hkl |
CCDC reference: 622698
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean () = 0.000 Å
- Disorder in main residue
- R factor = 0.031
- wR factor = 0.081
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.58 PLAT301_ALERT_3_B Main Residue Disorder ......................... 50.00 Perc. PLAT432_ALERT_2_B Short Inter X...Y Contact Br1 .. C10 .. 3.21 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.096 0.415 Tmin(prime) and Tmax expected: 0.101 0.344 RR(prime) = 0.789 Please check that your absorption correction is appropriate. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.83 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact Br2 .. C5 .. 3.27 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Br2 .. C4 .. 3.31 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.829 Tmax scaled 0.344 Tmin scaled 0.080 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 130
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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%.
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 Cl 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).
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.
For related tetrahalogenomercurates, see: Wang 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)[HgBrCl3] | F(000) = 1128 |
Mr = 601.15 | Dx = 2.111 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4607 reflections |
a = 15.9912 (8) Å | θ = 2.7–26.4° |
b = 8.7769 (5) Å | µ = 10.67 mm−1 |
c = 14.3189 (9) Å | T = 295 K |
β = 109.760 (1)° | Block, colourless |
V = 1891.4 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 3316 independent reflections |
Radiation source: fine-focus sealed tube | 2809 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→15 |
Tmin = 0.096, Tmax = 0.415 | k = −10→10 |
11857 measured reflections | l = −17→17 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0459P)2 + 0.263P] where P = (Fo2 + 2Fc2)/3 |
3316 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.77 e Å−3 |
130 restraints | Δρmin = −0.84 e Å−3 |
(C14H18N2)[HgBrCl3] | V = 1891.4 (2) Å3 |
Mr = 601.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.9912 (8) Å | µ = 10.67 mm−1 |
b = 8.7769 (5) Å | T = 295 K |
c = 14.3189 (9) Å | 0.20 × 0.20 × 0.10 mm |
β = 109.760 (1)° |
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 = 0.415 | Rint = 0.036 |
11857 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 130 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.77 e Å−3 |
3316 reflections | Δρmin = −0.84 e Å−3 |
210 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Hg1 | 0.254133 (15) | 0.47282 (3) | 0.529270 (15) | 0.05327 (11) | |
Br1 | 0.180 (3) | 0.253 (4) | 0.411 (2) | 0.0635 (18) | 0.218 (2) |
Br2 | 0.415 (3) | 0.435 (4) | 0.623 (3) | 0.0563 (12) | 0.136 (2) |
Br3 | 0.2771 (14) | 0.660 (2) | 0.4126 (18) | 0.0577 (7) | 0.090 (2) |
Br4 | 0.1650 (4) | 0.5446 (5) | 0.6389 (4) | 0.0643 (7) | 0.556 (2) |
Cl1 | 0.1756 (17) | 0.251 (3) | 0.4255 (15) | 0.0635 (18) | 0.782 (2) |
Cl2 | 0.4166 (11) | 0.4121 (14) | 0.6159 (11) | 0.0563 (12) | 0.864 (2) |
Cl3 | 0.2607 (3) | 0.6920 (5) | 0.4159 (4) | 0.0577 (7) | 0.910 (2) |
Cl4 | 0.1718 (14) | 0.5153 (17) | 0.6513 (14) | 0.0643 (7) | 0.444 (2) |
N1 | 0.5444 (6) | 0.0632 (18) | 0.3892 (8) | 0.0415 (18) | 0.50 |
C1 | 0.5126 (7) | 0.2014 (16) | 0.4108 (11) | 0.049 (2) | 0.50 |
H1 | 0.5517 | 0.2820 | 0.4356 | 0.059* | 0.50 |
C2 | 0.4226 (8) | 0.2193 (12) | 0.3955 (13) | 0.047 (3) | 0.50 |
H2 | 0.4014 | 0.3118 | 0.4100 | 0.057* | 0.50 |
C3 | 0.3643 (6) | 0.0990 (12) | 0.3585 (9) | 0.045 (3) | 0.50 |
H3 | 0.3041 | 0.1109 | 0.3482 | 0.054* | 0.50 |
C4 | 0.3960 (8) | −0.0393 (12) | 0.3368 (10) | 0.047 (3) | 0.50 |
H4 | 0.3570 | −0.1198 | 0.3121 | 0.056* | 0.50 |
C5 | 0.4861 (8) | −0.0572 (14) | 0.3522 (10) | 0.045 (2) | 0.50 |
H5 | 0.5073 | −0.1497 | 0.3377 | 0.054* | 0.50 |
N2 | 0.8831 (4) | −0.0935 (9) | 0.3268 (6) | 0.051 (2) | 0.50 |
C6 | 0.9378 (8) | −0.1770 (12) | 0.4066 (7) | 0.071 (2) | 0.50 |
H6 | 0.9134 | −0.2292 | 0.4479 | 0.085* | 0.50 |
C7 | 1.0288 (7) | −0.1824 (17) | 0.4249 (8) | 0.056 (2) | 0.50 |
H7 | 1.0654 | −0.2382 | 0.4783 | 0.067* | 0.50 |
C8 | 1.0651 (4) | −0.1044 (18) | 0.3632 (10) | 0.058 (3) | 0.50 |
H8 | 1.1260 | −0.1080 | 0.3754 | 0.070* | 0.50 |
C9 | 1.0104 (7) | −0.0209 (15) | 0.2834 (9) | 0.074 (2) | 0.50 |
H9 | 1.0348 | 0.0313 | 0.2421 | 0.089* | 0.50 |
C10 | 0.9194 (7) | −0.0155 (10) | 0.2651 (6) | 0.058 (3) | 0.50 |
H10 | 0.8828 | 0.0403 | 0.2117 | 0.070* | 0.50 |
C11 | 0.6368 (10) | 0.020 (4) | 0.4005 (15) | 0.055 (3) | 0.50 |
H11A | 0.6758 | 0.0525 | 0.4654 | 0.066* | 0.50 |
H11B | 0.6407 | −0.0897 | 0.3971 | 0.066* | 0.50 |
C12 | 0.6673 (6) | 0.0893 (13) | 0.3235 (9) | 0.060 (3) | 0.50 |
H12A | 0.6549 | 0.1977 | 0.3197 | 0.072* | 0.50 |
H12B | 0.6347 | 0.0447 | 0.2595 | 0.072* | 0.50 |
C13 | 0.7646 (6) | 0.0649 (11) | 0.3455 (9) | 0.065 (2) | 0.50 |
H13A | 0.7945 | 0.0679 | 0.4167 | 0.078* | 0.50 |
H13B | 0.7879 | 0.1473 | 0.3164 | 0.078* | 0.50 |
C14 | 0.7849 (5) | −0.0846 (11) | 0.3060 (8) | 0.058 (2) | 0.50 |
H14A | 0.7659 | −0.1685 | 0.3381 | 0.069* | 0.50 |
H14B | 0.7535 | −0.0911 | 0.2352 | 0.069* | 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' | 0.5785 | 0.2553 | 0.4171 | 0.059* | 0.50 |
C2' | 0.4467 (8) | 0.2480 (12) | 0.3944 (13) | 0.047 (3) | 0.50 |
H2' | 0.4401 | 0.3511 | 0.4053 | 0.057* | 0.50 |
C3' | 0.3737 (6) | 0.1514 (12) | 0.3711 (10) | 0.045 (3) | 0.50 |
H3' | 0.3182 | 0.1898 | 0.3664 | 0.054* | 0.50 |
C4' | 0.3835 (7) | −0.0027 (12) | 0.3549 (10) | 0.047 (3) | 0.50 |
H4' | 0.3346 | −0.0673 | 0.3393 | 0.056* | 0.50 |
C5' | 0.4664 (8) | −0.0601 (13) | 0.3619 (10) | 0.045 (2) | 0.50 |
H5' | 0.4730 | −0.1632 | 0.3510 | 0.054* | 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 | −0.2062 | 0.4590 | 0.085* | 0.50 |
C7' | 1.0227 (8) | −0.1965 (15) | 0.4003 (9) | 0.056 (2) | 0.50 |
H7' | 1.0552 | −0.2785 | 0.4355 | 0.067* | 0.50 |
C8' | 1.0525 (5) | −0.1173 (17) | 0.3336 (10) | 0.058 (3) | 0.50 |
H8' | 1.1051 | −0.1463 | 0.3242 | 0.070* | 0.50 |
C9' | 1.0039 (8) | 0.0051 (14) | 0.2810 (9) | 0.074 (2) | 0.50 |
H9' | 1.0239 | 0.0581 | 0.2363 | 0.089* | 0.50 |
C10' | 0.9254 (7) | 0.0485 (10) | 0.2951 (7) | 0.058 (3) | 0.50 |
H10' | 0.8929 | 0.1304 | 0.2598 | 0.070* | 0.50 |
C11' | 0.6329 (11) | −0.004 (4) | 0.3962 (13) | 0.055 (3) | 0.50 |
H11C | 0.6735 | 0.0614 | 0.4456 | 0.066* | 0.50 |
H11D | 0.6447 | −0.1086 | 0.4186 | 0.066* | 0.50 |
C12' | 0.6475 (5) | 0.0143 (14) | 0.2997 (8) | 0.060 (3) | 0.50 |
H12C | 0.6470 | 0.1219 | 0.2840 | 0.072* | 0.50 |
H12D | 0.5991 | −0.0341 | 0.2479 | 0.072* | 0.50 |
C13' | 0.7332 (5) | −0.0535 (14) | 0.3013 (8) | 0.065 (2) | 0.50 |
H13C | 0.7332 | −0.1614 | 0.3161 | 0.078* | 0.50 |
H13D | 0.7383 | −0.0435 | 0.2359 | 0.078* | 0.50 |
C14' | 0.8112 (5) | 0.0193 (12) | 0.3753 (8) | 0.058 (2) | 0.50 |
H14C | 0.8126 | −0.0073 | 0.4416 | 0.069* | 0.50 |
H14D | 0.8058 | 0.1291 | 0.3684 | 0.069* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.05137 (18) | 0.04907 (17) | 0.06456 (16) | −0.00278 (9) | 0.02638 (13) | −0.00031 (10) |
Br1 | 0.068 (3) | 0.0608 (8) | 0.076 (5) | −0.0161 (14) | 0.043 (3) | −0.018 (3) |
Br2 | 0.0542 (9) | 0.047 (4) | 0.061 (2) | 0.011 (3) | 0.0108 (12) | −0.007 (2) |
Br3 | 0.047 (2) | 0.055 (2) | 0.0626 (8) | −0.0058 (11) | 0.0074 (12) | 0.0138 (13) |
Br4 | 0.0685 (12) | 0.0632 (19) | 0.0745 (16) | 0.0078 (13) | 0.0418 (12) | 0.0016 (11) |
Cl1 | 0.068 (3) | 0.0608 (8) | 0.076 (5) | −0.0161 (14) | 0.043 (3) | −0.018 (3) |
Cl2 | 0.0542 (9) | 0.047 (4) | 0.061 (2) | 0.011 (3) | 0.0108 (12) | −0.007 (2) |
Cl3 | 0.047 (2) | 0.055 (2) | 0.0626 (8) | −0.0058 (11) | 0.0074 (12) | 0.0138 (13) |
Cl4 | 0.0685 (12) | 0.0632 (19) | 0.0745 (16) | 0.0078 (13) | 0.0418 (12) | 0.0016 (11) |
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) |
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) |
Hg1—Cl1 | 2.51 (2) | C13—H13A | 0.97 |
Hg1—Br1 | 2.58 (4) | C13—H13B | 0.97 |
Hg1—Cl2 | 2.529 (15) | C14—H14A | 0.97 |
Hg1—Br2 | 2.49 (4) | C14—H14B | 0.97 |
Hg1—Cl3 | 2.543 (5) | N1'—C1' | 1.39 |
Hg1—Br3 | 2.46 (2) | N1'—C5' | 1.39 |
Hg1—Cl4 | 2.545 (18) | N1'—C11' | 1.491 (8) |
Hg1—Br4 | 2.530 (5) | C1'—C2' | 1.39 |
N1—C1 | 1.39 | C1'—H1' | 0.93 |
N1—C5 | 1.39 | C2'—C3' | 1.39 |
N1—C11 | 1.479 (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' | 1.492 (8) |
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 | 1.498 (8) | 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' | 1.486 (9) |
C9—C10 | 1.39 | C11'—H11C | 0.97 |
C9—H9 | 0.93 | C11'—H11D | 0.97 |
C10—H10 | 0.93 | C12'—C13' | 1.487 (8) |
C11—C12 | 1.478 (9) | C12'—H12C | 0.97 |
C11—H11A | 0.97 | C12'—H12D | 0.97 |
C11—H11B | 0.97 | C13'—C14' | 1.481 (8) |
C12—C13 | 1.494 (8) | C13'—H13C | 0.97 |
C12—H12A | 0.97 | C13'—H13D | 0.97 |
C12—H12B | 0.97 | C14'—H14C | 0.97 |
C13—C14 | 1.506 (8) | C14'—H14D | 0.97 |
Cl2—Hg1—Br2 | 5.1 (9) | C13—C12—H12B | 109.3 |
Cl2—Hg1—Cl3 | 102.4 (4) | H12A—C12—H12B | 108.0 |
Br2—Hg1—Cl3 | 100.6 (11) | C12—C13—C14 | 112.8 (7) |
Cl2—Hg1—Br3 | 96.3 (6) | C12—C13—H13A | 109.0 |
Br2—Hg1—Br3 | 95.1 (12) | C14—C13—H13A | 109.0 |
Cl3—Hg1—Br3 | 8.9 (4) | C12—C13—H13B | 109.0 |
Cl2—Hg1—Cl4 | 112.2 (6) | C14—C13—H13B | 109.0 |
Br2—Hg1—Cl4 | 109.4 (10) | H13A—C13—H13B | 107.8 |
Cl3—Hg1—Cl4 | 118.0 (3) | N2—C14—C13 | 108.4 (6) |
Br3—Hg1—Cl4 | 126.8 (5) | N2—C14—H14A | 110.0 |
Cl2—Hg1—Br4 | 116.7 (3) | C13—C14—H14A | 110.0 |
Br2—Hg1—Br4 | 113.4 (9) | N2—C14—H14B | 110.0 |
Cl3—Hg1—Br4 | 111.18 (10) | C13—C14—H14B | 110.0 |
Br3—Hg1—Br4 | 120.0 (4) | H14A—C14—H14B | 108.4 |
Cl4—Hg1—Br4 | 7.0 (4) | C1'—N1'—C5' | 120.0 |
Cl2—Hg1—Cl1 | 110.7 (7) | C1'—N1'—C11' | 112.4 (16) |
Br2—Hg1—Cl1 | 115.8 (9) | C5'—N1'—C11' | 127.6 (16) |
Cl3—Hg1—Cl1 | 109.2 (5) | C2'—C1'—N1' | 120.0 |
Br3—Hg1—Cl1 | 106.0 (7) | C2'—C1'—H1' | 120.0 |
Cl4—Hg1—Cl1 | 104.4 (6) | N1'—C1'—H1' | 120.0 |
Br4—Hg1—Cl1 | 106.6 (5) | C1'—C2'—C3' | 120.0 |
Cl2—Hg1—Br1 | 109.3 (9) | C1'—C2'—H2' | 120.0 |
Br2—Hg1—Br1 | 114.4 (11) | C3'—C2'—H2' | 120.0 |
Cl3—Hg1—Br1 | 104.8 (8) | C4'—C3'—C2' | 120.0 |
Br3—Hg1—Br1 | 101.2 (9) | C4'—C3'—H3' | 120.0 |
Cl4—Hg1—Br1 | 109.5 (8) | C2'—C3'—H3' | 120.0 |
Br4—Hg1—Br1 | 111.5 (7) | C3'—C4'—C5' | 120.0 |
Cl1—Hg1—Br1 | 5.4 (10) | C3'—C4'—H4' | 120.0 |
C1—N1—C5 | 120.0 | C5'—C4'—H4' | 120.0 |
C1—N1—C11 | 128.6 (16) | C4'—C5'—N1' | 120.0 |
C5—N1—C11 | 111.4 (16) | C4'—C5'—H5' | 120.0 |
C2—C1—N1 | 120.0 | N1'—C5'—H5' | 120.0 |
C2—C1—H1 | 120.0 | C6'—N2'—C10' | 120.0 |
N1—C1—H1 | 120.0 | C6'—N2'—C14' | 121.5 (8) |
C1—C2—C3 | 120.0 | C10'—N2'—C14' | 118.5 (8) |
C1—C2—H2 | 120.0 | N2'—C6'—C7' | 120.0 |
C3—C2—H2 | 120.0 | N2'—C6'—H6' | 120.0 |
C4—C3—C2 | 120.0 | C7'—C6'—H6' | 120.0 |
C4—C3—H3 | 120.0 | C8'—C7'—C6' | 120.0 |
C2—C3—H3 | 120.0 | C8'—C7'—H7' | 120.0 |
C5—C4—C3 | 120.0 | C6'—C7'—H7' | 120.0 |
C5—C4—H4 | 120.0 | C7'—C8'—C9' | 120.0 |
C3—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 | 121.1 (8) | C9'—C10'—N2' | 120.0 |
C10—N2—C14 | 118.9 (8) | C9'—C10'—H10' | 120.0 |
N2—C6—C7 | 120.0 | N2'—C10'—H10' | 120.0 |
N2—C6—H6 | 120.0 | C12'—C11'—N1' | 110.0 (7) |
C7—C6—H6 | 120.0 | C12'—C11'—H11C | 109.7 |
C8—C7—C6 | 120.0 | N1'—C11'—H11C | 109.7 |
C8—C7—H7 | 120.0 | C12'—C11'—H11D | 109.7 |
C6—C7—H7 | 120.0 | N1'—C11'—H11D | 109.7 |
C9—C8—C7 | 120.0 | H11C—C11'—H11D | 108.2 |
C9—C8—H8 | 120.0 | C11'—C12'—C13' | 112.1 (8) |
C7—C8—H8 | 120.0 | C11'—C12'—H12C | 109.2 |
C8—C9—C10 | 120.0 | C13'—C12'—H12C | 109.2 |
C8—C9—H9 | 120.0 | C11'—C12'—H12D | 109.2 |
C10—C9—H9 | 120.0 | C13'—C12'—H12D | 109.2 |
C9—C10—N2 | 120.0 | H12C—C12'—H12D | 107.9 |
C9—C10—H10 | 120.0 | C14'—C13'—C12' | 112.8 (7) |
N2—C10—H10 | 120.0 | C14'—C13'—H13C | 109.0 |
C12—C11—N1 | 112.6 (8) | C12'—C13'—H13C | 109.0 |
C12—C11—H11A | 109.1 | C14'—C13'—H13D | 109.0 |
N1—C11—H11A | 109.1 | C12'—C13'—H13D | 109.0 |
C12—C11—H11B | 109.1 | H13C—C13'—H13D | 107.8 |
N1—C11—H11B | 109.1 | C13'—C14'—N2' | 111.1 (6) |
H11A—C11—H11B | 107.8 | C13'—C14'—H14C | 109.4 |
C11—C12—C13 | 111.5 (8) | N2'—C14'—H14C | 109.4 |
C11—C12—H12A | 109.3 | C13'—C14'—H14D | 109.4 |
C13—C12—H12A | 109.3 | N2'—C14'—H14D | 109.4 |
C11—C12—H12B | 109.3 | H14C—C14'—H14D | 108.0 |
C11—N1—C1—C2 | −179.6 (3) | C11'—N1'—C1'—C2' | −179.8 (2) |
C11—N1—C5—C4 | 179.7 (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—C9 | 179.4 (3) | C14'—N2'—C10'—C9' | 179.8 (3) |
C1—N1—C11—C12 | −74 (2) | C1'—N1'—C11'—C12' | −89 (2) |
C5—N1—C11—C12 | 106 (2) | C5'—N1'—C11'—C12' | 91 (2) |
N1—C11—C12—C13 | 171.0 (16) | N1'—C11'—C12'—C13' | −168.6 (16) |
C11—C12—C13—C14 | 86.6 (17) | C11'—C12'—C13'—C14' | −61.7 (19) |
C6—N2—C14—C13 | 100.1 (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—N2 | 176.8 (9) | C10'—N2'—C14'—C13' | 86.8 (11) |
Experimental details
Crystal data | |
Chemical formula | (C14H18N2)[HgBrCl3] |
Mr | 601.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 15.9912 (8), 8.7769 (5), 14.3189 (9) |
β (°) | 109.760 (1) |
V (Å3) | 1891.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 10.67 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.096, 0.415 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11857, 3316, 2809 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.081, 1.01 |
No. of reflections | 3316 |
No. of parameters | 210 |
No. of restraints | 130 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.77, −0.84 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
Hg1—Cl1 | 2.51 (2) | Hg1—Cl3 | 2.543 (5) |
Hg1—Br1 | 2.58 (4) | Hg1—Br3 | 2.46 (2) |
Hg1—Cl2 | 2.529 (15) | Hg1—Cl4 | 2.545 (18) |
Hg1—Br2 | 2.49 (4) | Hg1—Br4 | 2.530 (5) |
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.