Poly[hexa­bromo­bis­[μ₃-1,3,5-tris­(imidazol-1-ylmeth­yl)-2,4,6-trimethyl­benzene]trimercury(II)]

In the title compound, [Hg₃Br₆(C₂₁H₂₄N₆)₂]_n, the two Hg atoms (one of which lies on a twofold axis) are tetra­hedrally coordinated by two Br atoms and two imidazole N atoms from two different 1,3,5-tris­(imidazol-1-ylmeth­yl)-2,4,6-trimethyl­benzene ligands. The complex has an infinite one-dimensional chain structure. The chains are further connected by C—H...Br inter­actions to form a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.029
• wR factor = 0.032
• Data-to-parameter ratio = 20.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H2     ..  H23     ..       1.87 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: TEXSAN (Rigaku/MSC, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: TEXSAN.

Poly[bis[1,3,5-tris(imidazol-1-ylmethyl)-2,4,6- trimethylbenzene]hexabromotrimercury(II)]

Crystal data

[Hg3Br6(C21H24N6)2]	F(000) = 3336
Mr = 1802.15	Dx = 2.308 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2n 2ab	Cell parameters from 27136 reflections
a = 13.927 (9) Å	θ = 3.0–27.5°
b = 11.70 (1) Å	µ = 13.52 mm^−1
c = 31.83 (2) Å	T = 200 K
V = 5187 (7) Å^3	Block, colorless
Z = 4	0.18 × 0.10 × 0.04 mm

Data collection

Rigaku R-AXIS RAPID imaging-plate diffractometer	5935 independent reflections
Radiation source: fine-focus sealed tube	3388 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −18→18
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.220, Tmax = 0.582	l = −41→41
48822 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.032	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.003P)^2] where P = (Fo^2 + 2Fc^2)/3
5935 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 2.04 e Å^−3
0 restraints	Δρmin = −1.10 e Å^−3

Special details

Experimental. IR (KBr pellet, ν, cm^-1): 3102 s, 1627w, 1515 s, 1231 s, 1108 s, 827 m, 650 m.

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. 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 (Ų)

	x	y	z	Uiso*/Ueq
Hg1	0.5000	0.58834 (3)	0.2500	0.03276 (8)
Hg2	0.096847 (13)	0.052004 (18)	0.084252 (7)	0.03424 (6)
Br1	−0.00569 (4)	−0.09637 (5)	0.118535 (15)	0.05001 (16)
Br2	0.05663 (4)	0.25107 (5)	0.055797 (15)	0.03839 (15)
Br3	0.53463 (4)	0.70527 (5)	0.315939 (16)	0.04317 (16)
N11	0.7157 (3)	0.3159 (4)	0.22833 (13)	0.0296 (11)
N12	0.6243 (2)	0.4594 (3)	0.24697 (12)	0.0284 (10)
N31	0.3989 (3)	0.0489 (4)	0.13163 (11)	0.0294 (10)
N32	0.2468 (3)	0.0723 (4)	0.11479 (12)	0.0337 (12)
N51	0.7793 (3)	0.1359 (4)	0.02759 (12)	0.0279 (11)
N52	0.8501 (3)	0.0334 (4)	−0.02100 (12)	0.0372 (12)
C1	0.7012 (3)	0.1870 (4)	0.16584 (15)	0.0250 (13)
C2	0.6244 (3)	0.1123 (4)	0.16870 (14)	0.0246 (13)
C3	0.5766 (3)	0.0762 (4)	0.13261 (14)	0.0235 (13)
C4	0.6061 (3)	0.1138 (4)	0.09298 (14)	0.0266 (12)
C5	0.6837 (3)	0.1889 (4)	0.08985 (15)	0.0231 (12)
C6	0.7310 (3)	0.2286 (4)	0.12641 (16)	0.0275 (14)
C11	0.7582 (3)	0.2202 (4)	0.20445 (14)	0.0351 (15)
H1	0.7634	0.1528	0.2232	0.042*
H2	0.8240	0.2417	0.1957	0.042*
C12	0.6443 (3)	0.3853 (4)	0.21759 (15)	0.0310 (14)
H3	0.6116	0.3815	0.1915	0.037*
C13	0.6858 (4)	0.4376 (5)	0.27883 (15)	0.0375 (15)
H4	0.6881	0.4781	0.3047	0.045*
C14	0.7436 (4)	0.3493 (5)	0.26823 (15)	0.0406 (16)
H5	0.7933	0.3167	0.2848	0.049*
C21	0.5906 (3)	0.0731 (4)	0.21175 (12)	0.0436 (15)
H6	0.5207	0.0627	0.2113	0.052*
H7	0.6075	0.1309	0.2328	0.052*
H8	0.6216	0.0005	0.2189	0.052*
C31	0.4930 (3)	−0.0069 (4)	0.13637 (14)	0.0344 (13)
H9	0.4996	−0.0668	0.1146	0.041*
H10	0.4958	−0.0447	0.1642	0.041*
C32	0.3214 (4)	0.0041 (4)	0.11250 (15)	0.0367 (15)
H11	0.3208	−0.0682	0.0990	0.044*
C33	0.2772 (4)	0.1667 (5)	0.13554 (17)	0.0442 (17)
H12	0.2395	0.2327	0.1411	0.053*
C34	0.3704 (4)	0.1515 (5)	0.14713 (16)	0.0438 (16)
H13	0.4085	0.2031	0.1631	0.053*
C41	0.5557 (3)	0.0736 (4)	0.05374 (13)	0.0441 (15)
H14	0.5316	0.1399	0.0381	0.053*
H15	0.5019	0.0239	0.0615	0.053*
H16	0.6010	0.0310	0.0361	0.053*
C51	0.7190 (3)	0.2251 (4)	0.04690 (14)	0.0322 (15)
H17	0.6632	0.2408	0.0285	0.039*
H18	0.7566	0.2965	0.0495	0.039*
C52	0.7918 (3)	0.1186 (5)	−0.01331 (16)	0.0375 (15)
H19	0.7619	0.1630	−0.0346	0.045*
C53	0.8774 (3)	−0.0062 (4)	0.01750 (15)	0.0325 (15)
H20	0.9201	−0.0681	0.0224	0.039*
C54	0.8336 (3)	0.0571 (5)	0.04756 (15)	0.0330 (14)
H21	0.8399	0.0478	0.0771	0.040*
C61	0.8095 (3)	0.3166 (4)	0.12276 (15)	0.0421 (16)
H22	0.8663	0.2817	0.1099	0.051*
H23	0.8261	0.3451	0.1508	0.051*
H24	0.7872	0.3802	0.1053	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.02784 (16)	0.02646 (19)	0.04399 (18)	0.000	0.00030 (16)	0.000
Hg2	0.02989 (11)	0.03454 (13)	0.03829 (11)	−0.00274 (11)	0.00359 (11)	0.00004 (12)
Br1	0.0530 (4)	0.0481 (4)	0.0490 (4)	−0.0114 (3)	0.0073 (3)	0.0148 (3)
Br2	0.0492 (4)	0.0264 (3)	0.0395 (3)	−0.0003 (3)	0.0101 (3)	−0.0001 (3)
Br3	0.0342 (3)	0.0445 (4)	0.0508 (4)	−0.0003 (3)	−0.0008 (3)	−0.0164 (3)
N11	0.025 (3)	0.032 (3)	0.032 (3)	0.012 (2)	0.003 (2)	−0.001 (2)
N12	0.034 (2)	0.034 (3)	0.018 (2)	0.009 (2)	−0.005 (2)	−0.004 (3)
N31	0.018 (2)	0.025 (3)	0.044 (3)	0.000 (2)	0.002 (2)	−0.004 (2)
N32	0.020 (2)	0.039 (4)	0.042 (3)	0.004 (2)	−0.001 (2)	−0.008 (3)
N51	0.027 (3)	0.037 (3)	0.020 (3)	0.007 (2)	0.002 (2)	0.004 (2)
N52	0.038 (3)	0.045 (4)	0.029 (3)	0.004 (3)	0.010 (2)	−0.003 (3)
C1	0.019 (3)	0.026 (3)	0.030 (3)	0.007 (2)	0.000 (2)	−0.007 (3)
C2	0.022 (3)	0.023 (3)	0.029 (3)	0.007 (2)	0.006 (2)	0.000 (3)
C3	0.014 (3)	0.023 (4)	0.033 (3)	0.009 (2)	−0.001 (2)	0.001 (3)
C4	0.027 (3)	0.020 (3)	0.033 (3)	0.010 (3)	−0.007 (3)	−0.007 (3)
C5	0.024 (3)	0.023 (3)	0.022 (3)	0.004 (2)	0.005 (3)	−0.008 (3)
C6	0.018 (3)	0.022 (4)	0.043 (4)	0.004 (2)	0.008 (3)	−0.003 (3)
C11	0.026 (3)	0.038 (4)	0.041 (3)	0.012 (3)	−0.010 (3)	−0.006 (3)
C12	0.028 (3)	0.036 (4)	0.029 (3)	0.010 (3)	−0.013 (3)	−0.008 (3)
C13	0.058 (4)	0.036 (4)	0.019 (3)	0.008 (3)	−0.003 (3)	−0.007 (3)
C14	0.048 (4)	0.053 (5)	0.021 (3)	0.016 (3)	−0.008 (3)	−0.005 (3)
C21	0.046 (3)	0.054 (4)	0.031 (3)	0.000 (4)	0.004 (3)	−0.005 (3)
C31	0.025 (3)	0.031 (4)	0.046 (3)	0.002 (3)	0.001 (3)	−0.011 (3)
C32	0.030 (3)	0.033 (4)	0.046 (4)	−0.005 (3)	−0.001 (3)	−0.016 (3)
C33	0.021 (4)	0.032 (4)	0.079 (5)	0.000 (3)	−0.003 (3)	−0.010 (4)
C34	0.036 (4)	0.030 (4)	0.065 (4)	−0.009 (3)	0.000 (3)	−0.016 (3)
C41	0.045 (3)	0.044 (4)	0.043 (3)	−0.007 (3)	−0.004 (3)	−0.003 (3)
C51	0.038 (3)	0.031 (4)	0.028 (3)	0.009 (3)	0.006 (3)	−0.009 (3)
C52	0.034 (4)	0.051 (5)	0.028 (4)	0.012 (3)	−0.006 (3)	0.004 (3)
C53	0.037 (4)	0.031 (4)	0.029 (3)	−0.002 (3)	0.005 (3)	−0.004 (3)
C54	0.033 (3)	0.040 (4)	0.026 (3)	0.001 (3)	0.000 (3)	−0.002 (3)
C61	0.037 (3)	0.047 (5)	0.042 (4)	−0.013 (3)	0.000 (3)	−0.004 (3)

Geometric parameters (Å, º)

Hg1—N12^i	2.298 (4)	C4—C41	1.507 (5)
Hg1—N12	2.298 (4)	C5—C6	1.416 (6)
Hg1—Br3	2.5515 (14)	C5—C51	1.513 (6)
Hg1—Br3^i	2.5515 (14)	C6—C61	1.507 (6)
Hg2—N32	2.316 (4)	C11—H1	0.9900
Hg2—N52^ii	2.366 (4)	C11—H2	0.9900
Hg2—Br1	2.4987 (13)	C12—H3	0.9500
Hg2—Br2	2.5609 (19)	C13—C14	1.353 (6)
N11—C12	1.329 (5)	C13—H4	0.9500
N11—C14	1.384 (5)	C14—H5	0.9500
N11—C11	1.477 (5)	C21—H6	0.9800
N12—C12	1.305 (5)	C21—H7	0.9800
N12—C13	1.352 (5)	C21—H8	0.9800
N31—C32	1.345 (5)	C31—H9	0.9900
N31—C34	1.357 (6)	C31—H10	0.9900
N31—C31	1.472 (5)	C32—H11	0.9500
N32—C32	1.312 (5)	C33—C34	1.362 (6)
N32—C33	1.354 (6)	C33—H12	0.9500
N51—C52	1.329 (5)	C34—H13	0.9500
N51—C54	1.352 (5)	C41—H14	0.9800
N51—C51	1.473 (5)	C41—H15	0.9800
N52—C52	1.308 (6)	C41—H16	0.9800
N52—C53	1.365 (5)	C51—H17	0.9900
N52—Hg2^ii	2.366 (4)	C51—H18	0.9900
C1—C2	1.383 (6)	C52—H19	0.9500
C1—C6	1.409 (6)	C53—C54	1.354 (6)
C1—C11	1.514 (6)	C53—H20	0.9500
C2—C3	1.394 (6)	C54—H21	0.9500
C2—C21	1.520 (5)	C61—H22	0.9800
C3—C4	1.398 (6)	C61—H23	0.9800
C3—C31	1.522 (6)	C61—H24	0.9800
C4—C5	1.396 (6)
N12^i—Hg1—N12	97.9 (2)	N11—C12—H3	123.8
N12^i—Hg1—Br3	117.38 (10)	N12—C13—C14	109.5 (4)
N12—Hg1—Br3	104.13 (10)	N12—C13—H4	125.2
N12^i—Hg1—Br3^i	104.13 (10)	C14—C13—H4	125.2
N12—Hg1—Br3^i	117.38 (10)	C13—C14—N11	106.1 (5)
Br3—Hg1—Br3^i	115.15 (6)	C13—C14—H5	126.9
N32—Hg2—N52^ii	96.82 (14)	N11—C14—H5	126.9
N32—Hg2—Br1	113.79 (11)	C2—C21—H6	109.5
N52^ii—Hg2—Br1	104.88 (11)	C2—C21—H7	109.5
N32—Hg2—Br2	104.62 (11)	H6—C21—H7	109.5
N52^ii—Hg2—Br2	98.71 (12)	C2—C21—H8	109.5
Br1—Hg2—Br2	131.40 (4)	H6—C21—H8	109.5
C12—N11—C14	105.9 (4)	H7—C21—H8	109.5
C12—N11—C11	129.2 (4)	N31—C31—C3	113.0 (4)
C14—N11—C11	125.0 (4)	N31—C31—H9	109.0
C12—N12—C13	106.1 (4)	C3—C31—H9	109.0
C12—N12—Hg1	128.8 (3)	N31—C31—H10	109.0
C13—N12—Hg1	124.7 (3)	C3—C31—H10	109.0
C32—N31—C34	106.0 (4)	H9—C31—H10	107.8
C32—N31—C31	126.0 (4)	N32—C32—N31	111.9 (5)
C34—N31—C31	127.9 (4)	N32—C32—H11	124.1
C32—N32—C33	106.0 (4)	N31—C32—H11	124.1
C32—N32—Hg2	128.9 (4)	N32—C33—C34	108.9 (5)
C33—N32—Hg2	124.7 (3)	N32—C33—H12	125.6
C52—N51—C54	106.4 (4)	C34—C33—H12	125.6
C52—N51—C51	126.3 (4)	N31—C34—C33	107.2 (5)
C54—N51—C51	127.3 (4)	N31—C34—H13	126.4
C52—N52—C53	105.3 (4)	C33—C34—H13	126.4
C52—N52—Hg2^ii	132.4 (4)	C4—C41—H14	109.5
C53—N52—Hg2^ii	122.3 (3)	C4—C41—H15	109.5
C2—C1—C6	120.3 (4)	H14—C41—H15	109.5
C2—C1—C11	120.9 (5)	C4—C41—H16	109.5
C6—C1—C11	118.7 (5)	H14—C41—H16	109.5
C1—C2—C3	120.4 (4)	H15—C41—H16	109.5
C1—C2—C21	119.3 (4)	N51—C51—C5	111.4 (4)
C3—C2—C21	120.2 (4)	N51—C51—H17	109.4
C2—C3—C4	120.5 (4)	C5—C51—H17	109.4
C2—C3—C31	119.7 (4)	N51—C51—H18	109.4
C4—C3—C31	119.8 (4)	C5—C51—H18	109.4
C5—C4—C3	119.3 (4)	H17—C51—H18	108.0
C5—C4—C41	119.8 (4)	N52—C52—N51	112.4 (5)
C3—C4—C41	120.9 (4)	N52—C52—H19	123.8
C4—C5—C6	120.5 (4)	N51—C52—H19	123.8
C4—C5—C51	119.5 (4)	C54—C53—N52	108.9 (5)
C6—C5—C51	120.0 (4)	C54—C53—H20	125.6
C1—C6—C5	118.8 (5)	N52—C53—H20	125.6
C1—C6—C61	121.3 (5)	N51—C54—C53	107.0 (4)
C5—C6—C61	119.9 (4)	N51—C54—H21	126.5
N11—C11—C1	113.6 (4)	C53—C54—H21	126.5
N11—C11—H1	108.8	C6—C61—H22	109.5
C1—C11—H1	108.8	C6—C61—H23	109.5
N11—C11—H2	108.8	H22—C61—H23	109.5
C1—C11—H2	108.8	C6—C61—H24	109.5
H1—C11—H2	107.7	H22—C61—H24	109.5
N12—C12—N11	112.5 (4)	H23—C61—H24	109.5
N12—C12—H3	123.8
N12^i—Hg1—N12—C12	64.6 (4)	C2—C1—C11—N11	−84.8 (6)
Br3—Hg1—N12—C12	−174.5 (4)	C6—C1—C11—N11	98.8 (5)
Br3^i—Hg1—N12—C12	−45.9 (4)	C13—N12—C12—N11	0.0 (6)
N12^i—Hg1—N12—C13	−107.4 (4)	Hg1—N12—C12—N11	−173.1 (3)
Br3—Hg1—N12—C13	13.5 (4)	C14—N11—C12—N12	−0.1 (6)
Br3^i—Hg1—N12—C13	142.1 (4)	C11—N11—C12—N12	178.8 (4)
N52^ii—Hg2—N32—C32	−35.8 (5)	C12—N12—C13—C14	0.1 (6)
Br1—Hg2—N32—C32	73.7 (4)	Hg1—N12—C13—C14	173.6 (3)
Br2—Hg2—N32—C32	−136.7 (4)	N12—C13—C14—N11	−0.2 (6)
N52^ii—Hg2—N32—C33	136.7 (4)	C12—N11—C14—C13	0.2 (6)
Br1—Hg2—N32—C33	−113.7 (4)	C11—N11—C14—C13	−178.8 (5)
Br2—Hg2—N32—C33	35.9 (4)	C32—N31—C31—C3	143.4 (4)
C6—C1—C2—C3	0.9 (7)	C34—N31—C31—C3	−40.4 (6)
C11—C1—C2—C3	−175.5 (4)	C2—C3—C31—N31	103.2 (5)
C6—C1—C2—C21	−177.1 (4)	C4—C3—C31—N31	−78.1 (5)
C11—C1—C2—C21	6.5 (7)	C33—N32—C32—N31	1.2 (6)
C1—C2—C3—C4	0.7 (7)	Hg2—N32—C32—N31	174.9 (3)
C21—C2—C3—C4	178.7 (4)	C34—N31—C32—N32	0.5 (6)
C1—C2—C3—C31	179.4 (4)	C31—N31—C32—N32	177.4 (4)
C21—C2—C3—C31	−2.6 (7)	C32—N32—C33—C34	−2.5 (6)
C2—C3—C4—C5	−0.5 (7)	Hg2—N32—C33—C34	−176.5 (3)
C31—C3—C4—C5	−179.2 (4)	C32—N31—C34—C33	−2.0 (6)
C2—C3—C4—C41	179.1 (4)	C31—N31—C34—C33	−178.8 (4)
C31—C3—C4—C41	0.3 (7)	N32—C33—C34—N31	2.8 (6)
C3—C4—C5—C6	−1.3 (7)	C52—N51—C51—C5	153.1 (5)
C41—C4—C5—C6	179.2 (4)	C54—N51—C51—C5	−28.0 (6)
C3—C4—C5—C51	176.9 (4)	C4—C5—C51—N51	−79.0 (5)
C41—C4—C5—C51	−2.7 (7)	C6—C5—C51—N51	99.2 (5)
C2—C1—C6—C5	−2.6 (7)	C53—N52—C52—N51	−0.5 (6)
C11—C1—C6—C5	173.8 (4)	Hg2^ii—N52—C52—N51	177.7 (3)
C2—C1—C6—C61	175.4 (4)	C54—N51—C52—N52	0.4 (6)
C11—C1—C6—C61	−8.1 (7)	C51—N51—C52—N52	179.5 (4)
C4—C5—C6—C1	2.8 (7)	C52—N52—C53—C54	0.3 (6)
C51—C5—C6—C1	−175.4 (4)	Hg2^ii—N52—C53—C54	−178.1 (3)
C4—C5—C6—C61	−175.3 (4)	C52—N51—C54—C53	−0.2 (6)
C51—C5—C6—C61	6.6 (7)	C51—N51—C54—C53	−179.3 (4)
C12—N11—C11—C1	−10.7 (7)	N52—C53—C54—N51	0.0 (6)
C14—N11—C11—C1	168.0 (5)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H3···Br1^iii	0.95	2.76	3.703 (6)	171
C14—H5···Br3^iv	0.95	2.90	3.832 (6)	166

Symmetry codes: (iii) −x+1/2, y+1/2, z; (iv) −x+3/2, y−1/2, z.