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A new 2,2′-bi-1H-benzimidazole bridging organic ligand, namely 1,1′-bis­(pyridin-4-ylmeth­yl)-2,2′-bi-1H-benzimidazole, C26H20N6, L or (I), has been synthesized and used to create three new one-dimensional coordination polymers, viz. catena-poly[[di­chlorido­mercury(II)]-μ-1,1′-bis­(pyridin-4-ylmeth­yl)-2,2′-bi-1H-benzimidazole], [HgCl2(C26H20N6)]n, (II), and the bromido, [HgBr2(C26H20N6)]n, (III), and iodido, [HgI2(C26H20N6)]n, (IV), analogues. Free ligand L crystallizes with two symmetry-independent half-mol­ecules in the asymmetric unit and each L mol­ecule resides on a crytallographic inversion centre. In structures (II)–(IV), the L ligand is also positioned on a crystallographic inversion centre, whereas the Hg centre resides on a crystallographic twofold axis. Com­pound (I) adopts an anti conformation in the solid state and forms a two-dimensional network in the crystallographic bc plane via π–π and C—H...π inter­actions. The three HgII coordination complexes, (II)–(IV), have one-dimensional zigzag chains composed of L and HgX2 (X = Cl, Br and I), and the HgII centres are in a distorted tetra­hedral [HgX2N2] coordination geometry. Complexes (III) and (IV) are iso­morphous, whereas complex (II) displays an inter­esting conformational difference from the others, i.e. a twist in the flexible bridging ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613031598/gz3240sup1.cif
Contains datablocks global, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240IVsup5.hkl
Contains datablock IV

CCDC references: 972772; 972773; 972774; 972775

Computing details top

For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) 1,1'-Bis(pyridin-4-ylmethyl)-2,2'-bi-1H-benzimidazole top
Crystal data top
C26H20N6Z = 2
Mr = 416.48F(000) = 436
Triclinic, P1Dx = 1.348 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.094 (4) ÅCell parameters from 1073 reflections
b = 10.183 (4) Åθ = 2.4–22.6°
c = 10.972 (4) ŵ = 0.08 mm1
α = 106.389 (5)°T = 298 K
β = 103.167 (5)°Block, yellow
γ = 98.409 (5)°0.21 × 0.14 × 0.10 mm
V = 1026.4 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3762 independent reflections
Radiation source: fine-focus sealed tube2341 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
phi and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1212
Tmin = 0.986, Tmax = 0.992k = 128
5451 measured reflectionsl = 1013
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0943P)2]
where P = (Fo2 + 2Fc2)/3
3762 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.28 e Å3
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. 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
C10.4589 (4)0.0172 (4)0.1635 (4)0.0661 (10)
H10.41610.10780.15520.079*
C20.3778 (4)0.0619 (3)0.1108 (3)0.0568 (9)
H20.28270.02540.07030.068*
C30.4378 (3)0.1945 (3)0.1182 (3)0.0427 (7)
C40.5782 (3)0.2430 (3)0.1807 (3)0.0535 (9)
H40.62400.33250.18870.064*
C50.6503 (4)0.1551 (4)0.2316 (3)0.0600 (9)
H50.74550.18900.27330.072*
C60.3519 (3)0.2804 (3)0.0548 (3)0.0503 (8)
H6A0.34280.24990.03940.060*
H6B0.25900.26220.06560.060*
C70.4875 (3)0.5212 (3)0.0652 (3)0.0414 (7)
C80.4107 (3)0.5116 (3)0.2359 (3)0.0446 (8)
C90.4877 (3)0.6449 (3)0.2585 (3)0.0468 (8)
C100.5095 (4)0.7521 (4)0.3783 (3)0.0604 (9)
H100.56040.84220.39480.072*
C110.4526 (4)0.7180 (4)0.4694 (4)0.0660 (10)
H110.46710.78640.55080.079*
C120.3733 (4)0.5841 (4)0.4454 (4)0.0637 (10)
H120.33380.56680.50970.076*
C130.3525 (3)0.4777 (4)0.3292 (3)0.0551 (9)
H130.30200.38760.31350.066*
C140.0140 (3)0.5264 (3)0.5713 (3)0.0413 (7)
C150.0878 (3)0.5416 (3)0.7811 (3)0.0456 (8)
C160.0232 (3)0.6517 (3)0.7687 (3)0.0473 (8)
C170.0148 (4)0.7520 (4)0.8792 (4)0.0612 (10)
H170.02830.82520.87150.073*
C180.0719 (4)0.7413 (4)1.0015 (4)0.0678 (11)
H180.06750.80791.07760.081*
C190.1369 (4)0.6304 (4)1.0125 (4)0.0678 (11)
H190.17580.62591.09620.081*
C200.1445 (3)0.5300 (4)0.9045 (3)0.0580 (9)
H200.18610.45600.91260.070*
C210.1332 (3)0.3328 (3)0.6268 (3)0.0511 (8)
H21A0.22640.35080.68570.061*
H21B0.13990.30660.53670.061*
C220.0419 (3)0.2130 (3)0.6430 (3)0.0448 (8)
C230.1013 (3)0.1973 (4)0.6203 (3)0.0555 (9)
H230.14500.26430.59660.067*
C240.1775 (4)0.0819 (4)0.6332 (4)0.0681 (11)
H240.27320.07390.61810.082*
C250.0122 (5)0.0037 (4)0.6856 (4)0.0721 (11)
H250.05270.07370.70670.087*
C260.0983 (4)0.1086 (3)0.6771 (3)0.0538 (9)
H260.19390.11430.69420.065*
N10.5940 (3)0.0277 (3)0.2252 (3)0.0631 (8)
N20.4121 (3)0.4319 (2)0.1107 (2)0.0440 (6)
N30.5341 (3)0.6494 (3)0.1504 (2)0.0491 (7)
N40.0216 (3)0.6393 (3)0.6362 (2)0.0480 (7)
N50.0810 (3)0.4621 (2)0.6554 (2)0.0454 (7)
N60.1243 (4)0.0196 (3)0.6660 (3)0.0762 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.070 (3)0.042 (2)0.083 (3)0.0096 (19)0.016 (2)0.0215 (19)
C20.045 (2)0.045 (2)0.075 (2)0.0044 (16)0.0062 (17)0.0237 (18)
C30.0409 (18)0.0437 (18)0.0431 (17)0.0078 (15)0.0110 (13)0.0152 (14)
C40.045 (2)0.0462 (19)0.068 (2)0.0060 (16)0.0105 (16)0.0233 (17)
C50.043 (2)0.062 (2)0.078 (3)0.0157 (18)0.0138 (17)0.027 (2)
C60.0442 (19)0.0454 (19)0.0529 (19)0.0010 (15)0.0001 (14)0.0190 (16)
C70.0342 (16)0.0380 (17)0.0506 (17)0.0125 (14)0.0018 (13)0.0182 (15)
C80.0327 (16)0.0485 (19)0.057 (2)0.0176 (15)0.0050 (14)0.0255 (16)
C90.0360 (17)0.051 (2)0.055 (2)0.0221 (15)0.0066 (14)0.0187 (16)
C100.061 (2)0.052 (2)0.063 (2)0.0231 (18)0.0131 (18)0.0111 (18)
C110.062 (2)0.079 (3)0.053 (2)0.032 (2)0.0117 (18)0.011 (2)
C120.053 (2)0.083 (3)0.059 (2)0.028 (2)0.0145 (17)0.026 (2)
C130.0417 (19)0.063 (2)0.068 (2)0.0195 (17)0.0081 (16)0.0338 (19)
C140.0355 (17)0.0366 (16)0.0543 (17)0.0120 (14)0.0063 (14)0.0220 (15)
C150.0358 (17)0.0479 (19)0.052 (2)0.0072 (15)0.0065 (14)0.0210 (16)
C160.0427 (18)0.0427 (18)0.053 (2)0.0018 (15)0.0116 (14)0.0156 (16)
C170.062 (2)0.052 (2)0.068 (2)0.0067 (18)0.0186 (19)0.0195 (19)
C180.069 (3)0.069 (3)0.057 (2)0.004 (2)0.0188 (19)0.013 (2)
C190.059 (2)0.083 (3)0.054 (2)0.003 (2)0.0057 (17)0.025 (2)
C200.044 (2)0.072 (2)0.058 (2)0.0114 (18)0.0055 (16)0.0310 (19)
C210.0426 (19)0.056 (2)0.063 (2)0.0263 (16)0.0109 (15)0.0278 (17)
C220.0495 (19)0.0436 (18)0.0411 (17)0.0201 (15)0.0067 (14)0.0135 (14)
C230.047 (2)0.052 (2)0.066 (2)0.0186 (17)0.0061 (16)0.0213 (17)
C240.058 (2)0.059 (2)0.083 (3)0.014 (2)0.020 (2)0.017 (2)
C250.093 (3)0.052 (2)0.092 (3)0.037 (2)0.038 (2)0.034 (2)
C260.060 (2)0.050 (2)0.059 (2)0.0294 (18)0.0170 (16)0.0211 (17)
N10.062 (2)0.0549 (19)0.078 (2)0.0198 (16)0.0182 (16)0.0281 (16)
N20.0424 (15)0.0386 (14)0.0480 (15)0.0101 (12)0.0032 (11)0.0167 (12)
N30.0462 (16)0.0450 (16)0.0546 (17)0.0136 (13)0.0069 (13)0.0182 (14)
N40.0518 (17)0.0404 (15)0.0551 (17)0.0143 (13)0.0117 (13)0.0214 (13)
N50.0400 (15)0.0429 (15)0.0556 (17)0.0157 (12)0.0072 (12)0.0217 (13)
N60.088 (3)0.053 (2)0.099 (3)0.0219 (19)0.039 (2)0.0302 (18)
Geometric parameters (Å, º) top
C1—N11.323 (4)C14—N41.317 (4)
C1—C21.376 (5)C14—N51.387 (4)
C1—H10.9300C14—C14ii1.448 (6)
C2—C31.369 (4)C15—N51.369 (4)
C2—H20.9300C15—C201.390 (4)
C3—C41.372 (4)C15—C161.399 (4)
C3—C61.513 (4)C16—C171.377 (4)
C4—C51.389 (5)C16—N41.383 (4)
C4—H40.9300C17—C181.376 (5)
C5—N11.314 (4)C17—H170.9300
C5—H50.9300C18—C191.406 (5)
C6—N21.466 (4)C18—H180.9300
C6—H6A0.9700C19—C201.355 (5)
C6—H6B0.9700C19—H190.9300
C7—N31.316 (4)C20—H200.9300
C7—N21.372 (4)C21—N51.468 (4)
C7—C7i1.464 (6)C21—C221.495 (4)
C8—C91.386 (4)C21—H21A0.9700
C8—C131.388 (4)C21—H21B0.9700
C8—N21.389 (4)C22—C261.378 (4)
C9—N31.380 (4)C22—C231.387 (4)
C9—C101.399 (4)C23—C241.368 (5)
C10—C111.360 (5)C23—H230.9300
C10—H100.9300C24—N61.330 (5)
C11—C121.397 (5)C24—H240.9300
C11—H110.9300C25—N61.324 (5)
C12—C131.370 (5)C25—C261.370 (5)
C12—H120.9300C25—H250.9300
C13—H130.9300C26—H260.9300
N1—C1—C2124.1 (3)C20—C15—C16121.3 (3)
N1—C1—H1118.0C17—C16—N4130.2 (3)
C2—C1—H1118.0C17—C16—C15120.5 (3)
C3—C2—C1119.6 (3)N4—C16—C15109.3 (3)
C3—C2—H2120.2C18—C17—C16118.2 (4)
C1—C2—H2120.2C18—C17—H17120.9
C2—C3—C4117.4 (3)C16—C17—H17120.9
C2—C3—C6120.4 (3)C17—C18—C19120.6 (3)
C4—C3—C6122.1 (3)C17—C18—H18119.7
C3—C4—C5118.4 (3)C19—C18—H18119.7
C3—C4—H4120.8C20—C19—C18121.8 (4)
C5—C4—H4120.8C20—C19—H19119.1
N1—C5—C4124.8 (3)C18—C19—H19119.1
N1—C5—H5117.6C19—C20—C15117.5 (4)
C4—C5—H5117.6C19—C20—H20121.2
N2—C6—C3113.4 (2)C15—C20—H20121.2
N2—C6—H6A108.9N5—C21—C22112.8 (2)
C3—C6—H6A108.9N5—C21—H21A109.0
N2—C6—H6B108.9C22—C21—H21A109.0
C3—C6—H6B108.9N5—C21—H21B109.0
H6A—C6—H6B107.7C22—C21—H21B109.0
N3—C7—N2113.0 (3)H21A—C21—H21B107.8
N3—C7—C7i123.4 (3)C26—C22—C23116.7 (3)
N2—C7—C7i123.6 (3)C26—C22—C21120.1 (3)
C9—C8—C13122.5 (3)C23—C22—C21123.1 (3)
C9—C8—N2105.6 (3)C24—C23—C22119.2 (3)
C13—C8—N2132.0 (3)C24—C23—H23120.4
N3—C9—C8110.5 (3)C22—C23—H23120.4
N3—C9—C10129.0 (3)N6—C24—C23124.7 (4)
C8—C9—C10120.5 (3)N6—C24—H24117.7
C11—C10—C9116.7 (3)C23—C24—H24117.7
C11—C10—H10121.6N6—C25—C26124.8 (3)
C9—C10—H10121.6N6—C25—H25117.6
C10—C11—C12122.5 (3)C26—C25—H25117.6
C10—C11—H11118.7C25—C26—C22119.4 (3)
C12—C11—H11118.7C25—C26—H26120.3
C13—C12—C11121.4 (3)C22—C26—H26120.3
C13—C12—H12119.3C5—N1—C1115.6 (3)
C11—C12—H12119.3C7—N2—C8106.0 (2)
C12—C13—C8116.4 (3)C7—N2—C6131.4 (3)
C12—C13—H13121.8C8—N2—C6122.4 (3)
C8—C13—H13121.8C7—N3—C9105.0 (3)
N4—C14—N5112.1 (3)C14—N4—C16105.8 (3)
N4—C14—C14ii124.4 (3)C15—N5—C14106.3 (3)
N5—C14—C14ii123.4 (3)C15—N5—C21122.8 (3)
N5—C15—C20132.3 (3)C14—N5—C21130.8 (3)
N5—C15—C16106.5 (3)C25—N6—C24115.3 (3)
N1—C1—C2—C31.5 (6)N6—C25—C26—C221.5 (6)
C1—C2—C3—C40.8 (5)C23—C22—C26—C250.6 (5)
C1—C2—C3—C6176.9 (3)C21—C22—C26—C25177.1 (3)
C2—C3—C4—C50.2 (5)C4—C5—N1—C10.9 (5)
C6—C3—C4—C5177.5 (3)C2—C1—N1—C51.5 (6)
C3—C4—C5—N10.3 (5)N3—C7—N2—C80.3 (3)
C2—C3—C6—N2158.5 (3)C7i—C7—N2—C8179.1 (3)
C4—C3—C6—N223.9 (4)N3—C7—N2—C6174.3 (3)
C13—C8—C9—N3179.5 (3)C7i—C7—N2—C66.3 (5)
N2—C8—C9—N30.9 (3)C9—C8—N2—C70.7 (3)
C13—C8—C9—C100.2 (5)C13—C8—N2—C7179.1 (3)
N2—C8—C9—C10178.8 (3)C9—C8—N2—C6174.5 (2)
N3—C9—C10—C11179.2 (3)C13—C8—N2—C64.0 (5)
C8—C9—C10—C110.4 (5)C3—C6—N2—C7101.2 (3)
C9—C10—C11—C121.4 (5)C3—C6—N2—C872.6 (4)
C10—C11—C12—C132.2 (5)N2—C7—N3—C90.3 (3)
C11—C12—C13—C81.9 (5)C7i—C7—N3—C9179.7 (3)
C9—C8—C13—C120.9 (5)C8—C9—N3—C70.8 (3)
N2—C8—C13—C12179.1 (3)C10—C9—N3—C7178.9 (3)
N5—C15—C16—C17179.1 (3)N5—C14—N4—C160.1 (3)
C20—C15—C16—C170.3 (5)C14ii—C14—N4—C16179.6 (3)
N5—C15—C16—N40.4 (3)C17—C16—N4—C14178.8 (3)
C20—C15—C16—N4179.0 (3)C15—C16—N4—C140.2 (3)
N4—C16—C17—C18178.2 (3)C20—C15—N5—C14178.9 (3)
C15—C16—C17—C180.2 (5)C16—C15—N5—C140.4 (3)
C16—C17—C18—C190.0 (5)C20—C15—N5—C213.2 (5)
C17—C18—C19—C200.8 (6)C16—C15—N5—C21177.5 (3)
C18—C19—C20—C151.2 (5)N4—C14—N5—C150.4 (3)
N5—C15—C20—C19178.3 (3)C14ii—C14—N5—C15179.9 (3)
C16—C15—C20—C191.0 (5)N4—C14—N5—C21177.3 (3)
N5—C21—C22—C26151.8 (3)C14ii—C14—N5—C212.2 (6)
N5—C21—C22—C2330.8 (4)C22—C21—N5—C1572.9 (4)
C26—C22—C23—C240.3 (5)C22—C21—N5—C14104.5 (3)
C21—C22—C23—C24177.8 (3)C26—C25—N6—C241.4 (6)
C22—C23—C24—N60.4 (6)C23—C24—N6—C250.4 (6)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1.
(II) catena-Poly[[dichloridomercury(II)]-µ-1,1'-bis(pyridin-4-ylmethyl)-2,2'-bi-1H-benzimidazole] top
Crystal data top
[HgCl2(C26H20N6)]F(000) = 1328
Mr = 687.97Dx = 1.862 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2ycCell parameters from 2207 reflections
a = 29.641 (15) Åθ = 2.8–24.7°
b = 4.953 (2) ŵ = 6.52 mm1
c = 16.932 (8) ÅT = 298 K
β = 99.236 (11)°Plan, colourless
V = 2454 (2) Å30.20 × 0.10 × 0.04 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2293 independent reflections
Radiation source: fine-focus sealed tube1745 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
phi and ω scansθmax = 25.6°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 3629
Tmin = 0.356, Tmax = 0.781k = 65
6064 measured reflectionsl = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.033P)2]
where P = (Fo2 + 2Fc2)/3
2293 reflections(Δ/σ)max = 0.001
159 parametersΔρmax = 1.06 e Å3
0 restraintsΔρmin = 0.75 e Å3
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. 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
C10.04608 (19)0.6141 (13)0.3915 (4)0.0735 (17)
H10.01530.63500.39540.088*
C20.0770 (2)0.7553 (10)0.4436 (4)0.0680 (16)
H20.06720.87230.48040.082*
C30.12272 (17)0.7234 (9)0.4415 (3)0.0444 (12)
C40.13442 (16)0.5511 (11)0.3852 (3)0.0565 (13)
H40.16500.52160.38160.068*
C50.10072 (19)0.4217 (13)0.3341 (3)0.0654 (15)
H50.10950.30710.29580.078*
C60.15835 (16)0.8771 (9)0.4984 (3)0.0478 (12)
H6A0.17181.01570.46910.057*
H6B0.14380.96520.53890.057*
C70.23906 (17)0.6681 (9)0.5277 (2)0.0403 (10)
C80.18701 (16)0.5128 (9)0.5949 (2)0.0423 (11)
C90.22823 (17)0.3793 (9)0.6164 (3)0.0442 (12)
C100.2318 (2)0.1755 (10)0.6743 (3)0.0541 (13)
H100.25900.08180.68970.065*
C110.1939 (2)0.1202 (11)0.7073 (3)0.0604 (15)
H110.19530.01500.74570.072*
C120.1531 (2)0.2589 (10)0.6854 (3)0.0577 (15)
H120.12810.21430.70970.069*
C130.14858 (17)0.4585 (11)0.6292 (3)0.0524 (12)
H130.12140.55250.61480.063*
Cl10.04580 (5)0.0778 (4)0.15364 (10)0.0924 (5)
Hg10.00000.19383 (7)0.25000.07134 (16)
N10.05643 (14)0.4501 (10)0.3360 (2)0.0566 (11)
N20.19419 (14)0.6973 (7)0.5371 (2)0.0426 (9)
N30.26075 (13)0.4803 (8)0.5749 (2)0.0458 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.030 (3)0.091 (5)0.095 (4)0.013 (3)0.001 (3)0.006 (4)
C20.046 (4)0.078 (4)0.080 (4)0.015 (3)0.007 (3)0.021 (3)
C30.042 (3)0.047 (3)0.043 (3)0.006 (2)0.003 (2)0.009 (2)
C40.032 (3)0.083 (4)0.054 (3)0.001 (3)0.009 (2)0.015 (3)
C50.050 (4)0.092 (4)0.054 (3)0.001 (3)0.008 (3)0.017 (3)
C60.047 (3)0.039 (3)0.056 (3)0.005 (2)0.003 (2)0.001 (2)
C70.046 (3)0.037 (3)0.036 (2)0.003 (2)0.001 (2)0.009 (2)
C80.051 (3)0.040 (3)0.035 (2)0.006 (2)0.002 (2)0.010 (2)
C90.052 (3)0.037 (3)0.040 (2)0.006 (2)0.001 (2)0.004 (2)
C100.062 (4)0.048 (3)0.049 (3)0.001 (3)0.002 (3)0.004 (3)
C110.075 (4)0.055 (4)0.049 (3)0.012 (3)0.001 (3)0.004 (2)
C120.064 (4)0.061 (4)0.051 (3)0.019 (3)0.015 (3)0.007 (3)
C130.052 (3)0.051 (3)0.053 (3)0.005 (3)0.008 (2)0.008 (3)
Cl10.0523 (10)0.1269 (14)0.0996 (11)0.0066 (9)0.0175 (8)0.0222 (11)
Hg10.0383 (2)0.1028 (3)0.0689 (2)0.0000.00357 (14)0.000
N10.037 (2)0.076 (3)0.054 (2)0.002 (2)0.0026 (19)0.000 (2)
N20.044 (2)0.039 (2)0.042 (2)0.0003 (19)0.0011 (17)0.0023 (18)
N30.045 (2)0.047 (3)0.042 (2)0.001 (2)0.0022 (18)0.0004 (19)
Geometric parameters (Å, º) top
C1—N11.316 (7)C8—N21.380 (6)
C1—C21.359 (8)C8—C91.386 (6)
C1—H10.9300C8—C131.386 (6)
C2—C31.371 (7)C9—N31.374 (6)
C2—H20.9300C9—C101.400 (7)
C3—C41.365 (7)C10—C111.361 (8)
C3—C61.516 (7)C10—H100.9300
C4—C51.371 (7)C11—C121.388 (8)
C4—H40.9300C11—H110.9300
C5—N11.326 (6)C12—C131.363 (7)
C5—H50.9300C12—H120.9300
C6—N21.458 (6)C13—H130.9300
C6—H6A0.9700Hg1—N12.397 (4)
C6—H6B0.9700Hg1—N1ii2.397 (4)
C7—N31.324 (5)Hg1—Cl12.3553 (18)
C7—N21.372 (6)Hg1—Cl1ii2.3553 (18)
C7—C7i1.468 (10)
N1—C1—C2124.9 (5)N3—C9—C10129.8 (5)
N1—C1—H1117.6C8—C9—C10119.5 (5)
C2—C1—H1117.6C11—C10—C9117.2 (5)
C1—C2—C3119.3 (5)C11—C10—H10121.4
C1—C2—H2120.3C9—C10—H10121.4
C3—C2—H2120.3C10—C11—C12122.2 (5)
C4—C3—C2117.0 (5)C10—C11—H11118.9
C4—C3—C6122.0 (4)C12—C11—H11118.9
C2—C3—C6121.1 (4)C13—C12—C11122.0 (5)
C3—C4—C5119.5 (5)C13—C12—H12119.0
C3—C4—H4120.3C11—C12—H12119.0
C5—C4—H4120.3C12—C13—C8116.0 (5)
N1—C5—C4124.0 (5)C12—C13—H13122.0
N1—C5—H5118.0C8—C13—H13122.0
C4—C5—H5118.0N1—Hg1—N1ii116.0 (2)
N2—C6—C3111.2 (4)Cl1—Hg1—N197.25 (12)
N2—C6—H6A109.4Cl1ii—Hg1—N197.60 (11)
C3—C6—H6A109.4Cl1—Hg1—N1ii97.60 (11)
N2—C6—H6B109.4Cl1ii—Hg1—N1ii97.25 (12)
C3—C6—H6B109.4Cl1—Hg1—Cl1ii151.74 (10)
H6A—C6—H6B108.0C1—N1—C5115.3 (4)
N3—C7—N2112.9 (4)C1—N1—Hg1122.7 (3)
N3—C7—C7i123.5 (6)C5—N1—Hg1121.8 (4)
N2—C7—C7i123.5 (5)C7—N2—C8106.0 (4)
N2—C8—C9105.8 (4)C7—N2—C6131.5 (4)
N2—C8—C13131.1 (5)C8—N2—C6122.6 (4)
C9—C8—C13123.1 (5)C7—N3—C9104.6 (4)
N3—C9—C8110.7 (4)
N1—C1—C2—C32.1 (9)C4—C5—N1—Hg1175.9 (4)
C1—C2—C3—C40.9 (8)Cl1—Hg1—N1—C1164.5 (4)
C1—C2—C3—C6179.9 (5)Cl1ii—Hg1—N1—C139.6 (4)
C2—C3—C4—C50.4 (8)N1ii—Hg1—N1—C162.4 (4)
C6—C3—C4—C5178.6 (5)Cl1—Hg1—N1—C520.1 (4)
C3—C4—C5—N10.8 (9)Cl1ii—Hg1—N1—C5135.8 (4)
C4—C3—C6—N250.0 (6)N1ii—Hg1—N1—C5122.3 (4)
C2—C3—C6—N2131.0 (5)N3—C7—N2—C80.1 (5)
N2—C8—C9—N31.3 (5)C7i—C7—N2—C8178.9 (5)
C13—C8—C9—N3177.8 (4)N3—C7—N2—C6179.7 (4)
N2—C8—C9—C10179.6 (4)C7i—C7—N2—C60.9 (8)
C13—C8—C9—C101.3 (7)C9—C8—N2—C70.8 (4)
N3—C9—C10—C11178.5 (4)C13—C8—N2—C7178.3 (4)
C8—C9—C10—C110.4 (7)C9—C8—N2—C6179.4 (4)
C9—C10—C11—C120.3 (8)C13—C8—N2—C61.5 (7)
C10—C11—C12—C130.3 (8)C3—C6—N2—C7108.6 (5)
C11—C12—C13—C80.5 (7)C3—C6—N2—C871.6 (5)
N2—C8—C13—C12179.8 (4)N2—C7—N3—C90.9 (5)
C9—C8—C13—C121.3 (7)C7i—C7—N3—C9179.7 (5)
C2—C1—N1—C51.7 (9)C8—C9—N3—C71.4 (5)
C2—C1—N1—Hg1177.3 (5)C10—C9—N3—C7179.7 (4)
C4—C5—N1—C10.2 (8)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y, z+1/2.
(III) catena-Poly[[dibromidomercury(II)]-µ-1,1'-bis(pyridin-4-ylmethyl)-2,2'-bi-1H-benzimidazole] top
Crystal data top
[HgBr2(C26H20N6)]F(000) = 1472
Mr = 776.89Dx = 2.037 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -c2ycCell parameters from 3227 reflections
a = 24.494 (8) Åθ = 2.4–25.9°
b = 6.006 (2) ŵ = 9.26 mm1
c = 17.306 (6) ÅT = 298 K
β = 95.796 (4)°Block, colourless
V = 2532.8 (15) Å30.23 × 0.18 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2387 independent reflections
Radiation source: fine-focus sealed tube2101 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
phi and ω scansθmax = 25.6°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 2922
Tmin = 0.225, Tmax = 0.458k = 57
6393 measured reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0537P)2]
where P = (Fo2 + 2Fc2)/3
2387 reflections(Δ/σ)max = 0.001
159 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 1.35 e Å3
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. 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
C10.0507 (2)0.5005 (10)0.9059 (3)0.0543 (15)
H10.02910.60310.92920.065*
C20.0822 (2)0.3553 (10)0.9522 (3)0.0505 (14)
H20.08190.35991.00580.061*
C30.1150 (2)0.2002 (8)0.9183 (3)0.0377 (11)
C40.1135 (2)0.2007 (9)0.8392 (3)0.0462 (13)
H40.13460.09940.81440.055*
C50.0808 (3)0.3517 (10)0.7964 (3)0.0513 (14)
H50.08050.34970.74260.062*
C60.1503 (2)0.0404 (8)0.9690 (3)0.0401 (11)
H6A0.15090.08721.02270.048*
H6B0.13390.10670.96460.048*
C70.2518 (2)0.1531 (8)0.9745 (3)0.0353 (10)
C80.2264 (2)0.1381 (8)0.9033 (3)0.0371 (11)
C90.2823 (2)0.1007 (8)0.9044 (3)0.0385 (11)
C100.3151 (3)0.2426 (8)0.8651 (3)0.0463 (13)
H100.35270.21920.86570.056*
C110.2895 (3)0.4189 (9)0.8256 (3)0.0534 (15)
H110.31030.51750.79920.064*
C120.2334 (3)0.4529 (9)0.8241 (3)0.0542 (15)
H120.21760.57310.79630.065*
C130.2000 (3)0.3131 (8)0.8627 (3)0.0486 (13)
H130.16230.33540.86140.058*
Hg10.00000.77841 (5)0.75000.04575 (14)
Br10.05808 (4)0.90727 (16)0.84956 (4)0.0981 (3)
N10.04965 (17)0.5005 (8)0.8282 (2)0.0464 (11)
N20.20649 (16)0.0267 (6)0.9488 (2)0.0353 (9)
N30.29770 (18)0.0830 (6)0.9497 (2)0.0401 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.041 (3)0.074 (4)0.049 (3)0.021 (3)0.008 (3)0.004 (3)
C20.042 (3)0.071 (3)0.040 (3)0.015 (3)0.008 (2)0.002 (2)
C30.024 (3)0.043 (2)0.046 (3)0.004 (2)0.002 (2)0.001 (2)
C40.045 (3)0.049 (3)0.045 (3)0.010 (2)0.002 (2)0.012 (2)
C50.056 (4)0.059 (3)0.038 (3)0.012 (3)0.003 (3)0.007 (2)
C60.033 (3)0.041 (2)0.047 (3)0.001 (2)0.008 (2)0.003 (2)
C70.032 (3)0.039 (2)0.034 (2)0.005 (2)0.000 (2)0.0017 (19)
C80.039 (3)0.037 (2)0.035 (2)0.005 (2)0.000 (2)0.0017 (19)
C90.044 (3)0.040 (3)0.031 (2)0.011 (2)0.001 (2)0.0042 (19)
C100.045 (3)0.051 (3)0.045 (3)0.014 (2)0.011 (2)0.006 (2)
C110.075 (5)0.045 (3)0.042 (3)0.016 (3)0.016 (3)0.002 (2)
C120.073 (5)0.043 (3)0.047 (3)0.002 (3)0.008 (3)0.009 (2)
C130.051 (4)0.045 (3)0.050 (3)0.003 (3)0.006 (3)0.007 (2)
Hg10.0374 (2)0.0554 (2)0.04453 (19)0.0000.00467 (12)0.000
Br10.1052 (7)0.1223 (7)0.0746 (5)0.0701 (6)0.0467 (4)0.0372 (4)
N10.030 (3)0.067 (3)0.042 (2)0.010 (2)0.0012 (19)0.007 (2)
N20.027 (2)0.039 (2)0.040 (2)0.0041 (17)0.0032 (17)0.0009 (16)
N30.034 (3)0.043 (2)0.044 (2)0.0037 (19)0.0030 (18)0.0030 (18)
Geometric parameters (Å, º) top
C1—N11.343 (6)C8—C91.385 (7)
C1—C21.370 (8)C8—N21.385 (6)
C1—H10.9300C8—C131.388 (8)
C2—C31.396 (8)C9—N31.384 (6)
C2—H20.9300C9—C101.394 (7)
C3—C41.365 (7)C10—C111.377 (8)
C3—C61.513 (7)C10—H100.9300
C4—C51.376 (8)C11—C121.387 (9)
C4—H40.9300C11—H110.9300
C5—N11.330 (7)C12—C131.390 (8)
C5—H50.9300C12—H120.9300
C6—N21.455 (6)C13—H130.9300
C6—H6A0.9700Hg1—N1ii2.400 (4)
C6—H6B0.9700Hg1—N12.400 (4)
C7—N31.313 (6)Hg1—Br12.4671 (9)
C7—N21.380 (6)Hg1—Br1ii2.4671 (9)
C7—C7i1.470 (10)
N1—C1—C2122.6 (5)N3—C9—C10128.7 (5)
N1—C1—H1118.7C8—C9—C10120.8 (5)
C2—C1—H1118.7C11—C10—C9117.1 (6)
C1—C2—C3119.5 (5)C11—C10—H10121.4
C1—C2—H2120.2C9—C10—H10121.4
C3—C2—H2120.2C10—C11—C12121.5 (5)
C4—C3—C2117.5 (5)C10—C11—H11119.2
C4—C3—C6122.6 (5)C12—C11—H11119.2
C2—C3—C6119.9 (5)C11—C12—C13122.2 (5)
C3—C4—C5119.7 (5)C11—C12—H12118.9
C3—C4—H4120.2C13—C12—H12118.9
C5—C4—H4120.2C8—C13—C12115.7 (6)
N1—C5—C4123.2 (5)C8—C13—H13122.2
N1—C5—H5118.4C12—C13—H13122.2
C4—C5—H5118.4N1ii—Hg1—N191.9 (2)
N2—C6—C3113.4 (4)N1ii—Hg1—Br1108.46 (11)
N2—C6—H6A108.9N1—Hg1—Br196.87 (10)
C3—C6—H6A108.9N1ii—Hg1—Br1ii96.87 (10)
N2—C6—H6B108.9N1—Hg1—Br1ii108.46 (11)
C3—C6—H6B108.9Br1—Hg1—Br1ii143.43 (5)
H6A—C6—H6B107.7C5—N1—C1117.4 (5)
N3—C7—N2114.0 (4)C5—N1—Hg1120.9 (3)
N3—C7—C7i123.7 (6)C1—N1—Hg1121.5 (3)
N2—C7—C7i122.4 (6)C7—N2—C8104.9 (4)
C9—C8—N2106.4 (4)C7—N2—C6129.8 (4)
C9—C8—C13122.7 (5)C8—N2—C6125.0 (4)
N2—C8—C13131.0 (5)C7—N3—C9104.3 (4)
N3—C9—C8110.5 (4)
N1—C1—C2—C30.1 (10)C2—C1—N1—Hg1174.5 (5)
C1—C2—C3—C40.3 (9)N1ii—Hg1—N1—C559.3 (4)
C1—C2—C3—C6179.5 (5)Br1—Hg1—N1—C5168.2 (4)
C2—C3—C4—C50.4 (8)Br1ii—Hg1—N1—C538.6 (5)
C6—C3—C4—C5179.4 (5)N1ii—Hg1—N1—C1126.3 (5)
C3—C4—C5—N10.2 (10)Br1—Hg1—N1—C117.4 (4)
C4—C3—C6—N247.3 (7)Br1ii—Hg1—N1—C1135.9 (4)
C2—C3—C6—N2132.5 (5)N3—C7—N2—C80.2 (5)
N2—C8—C9—N30.2 (5)C7i—C7—N2—C8179.6 (5)
C13—C8—C9—N3179.5 (5)N3—C7—N2—C6174.1 (4)
N2—C8—C9—C10178.4 (4)C7i—C7—N2—C65.3 (9)
C13—C8—C9—C101.3 (7)C9—C8—N2—C70.0 (5)
N3—C9—C10—C11178.1 (5)C13—C8—N2—C7179.7 (5)
C8—C9—C10—C110.3 (7)C9—C8—N2—C6174.7 (4)
C9—C10—C11—C120.6 (8)C13—C8—N2—C65.0 (8)
C10—C11—C12—C130.6 (9)C3—C6—N2—C788.2 (6)
C9—C8—C13—C121.3 (8)C3—C6—N2—C898.4 (5)
N2—C8—C13—C12178.3 (5)N2—C7—N3—C90.3 (5)
C11—C12—C13—C80.4 (8)C7i—C7—N3—C9179.7 (6)
C4—C5—N1—C10.1 (9)C8—C9—N3—C70.3 (5)
C4—C5—N1—Hg1174.6 (5)C10—C9—N3—C7178.4 (5)
C2—C1—N1—C50.1 (9)
Symmetry codes: (i) x+1/2, y+1/2, z+2; (ii) x, y, z+3/2.
(IV) catena-Poly[[diiodidomercury(II)]-µ-1,1'-bis(pyridin-4-ylmethyl)-2,2'-bi-1H-benzimidazole] top
Crystal data top
[HgI2(C26H20N6)]F(000) = 1616
Mr = 870.87Dx = 2.156 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -c2ycCell parameters from 2156 reflections
a = 25.339 (9) Åθ = 2.6–21.8°
b = 6.056 (2) ŵ = 8.06 mm1
c = 17.683 (6) ÅT = 298 K
β = 98.619 (4)°Block, colourless
V = 2682.9 (16) Å30.16 × 0.12 × 0.09 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2526 independent reflections
Radiation source: fine-focus sealed tube1950 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
phi and ω scansθmax = 25.6°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 2530
Tmin = 0.359, Tmax = 0.531k = 76
6723 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0281P)2]
where P = (Fo2 + 2Fc2)/3
2526 reflections(Δ/σ)max < 0.001
159 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 1.19 e Å3
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. 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
C10.0544 (3)0.4861 (12)0.9012 (4)0.070 (2)
H10.03240.58070.92370.084*
C20.0866 (2)0.3435 (13)0.9476 (4)0.070 (2)
H20.08680.34491.00020.084*
C30.1185 (2)0.1987 (9)0.9154 (3)0.0445 (14)
C40.1174 (2)0.2097 (10)0.8381 (3)0.0574 (17)
H40.13860.11610.81380.069*
C50.0846 (2)0.3602 (11)0.7965 (4)0.0572 (16)
H50.08460.36640.74390.069*
C60.1538 (2)0.0365 (10)0.9658 (3)0.0482 (14)
H6A0.15490.07951.01890.058*
H6B0.13780.10920.95960.058*
C70.2517 (2)0.1563 (9)0.9751 (3)0.0425 (13)
C80.2271 (2)0.1350 (10)0.9037 (3)0.0467 (14)
C90.2813 (2)0.0919 (10)0.9059 (3)0.0463 (14)
C100.3128 (3)0.2277 (10)0.8663 (3)0.0570 (16)
H100.34900.20050.86690.068*
C110.2877 (3)0.4028 (11)0.8267 (3)0.0638 (18)
H110.30760.49790.80080.077*
C120.2336 (3)0.4418 (11)0.8242 (4)0.0695 (19)
H120.21820.56130.79610.083*
C130.2021 (3)0.3098 (10)0.8619 (4)0.0611 (17)
H130.16570.33600.85950.073*
Hg10.00000.77000 (6)0.75000.05394 (13)
I10.05707 (3)0.90708 (11)0.85377 (3)0.1074 (3)
N10.05302 (18)0.4963 (9)0.8265 (3)0.0548 (13)
N20.20830 (17)0.0240 (8)0.9488 (3)0.0437 (11)
N30.29606 (17)0.0913 (8)0.9509 (3)0.0473 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.059 (4)0.094 (5)0.060 (4)0.032 (4)0.014 (3)0.007 (4)
C20.059 (4)0.101 (6)0.054 (4)0.031 (4)0.020 (3)0.012 (4)
C30.036 (3)0.051 (4)0.047 (3)0.001 (3)0.006 (3)0.001 (3)
C40.055 (4)0.060 (4)0.056 (4)0.016 (3)0.006 (3)0.011 (3)
C50.061 (4)0.063 (4)0.047 (4)0.008 (3)0.003 (3)0.007 (3)
C60.042 (3)0.050 (4)0.052 (3)0.004 (3)0.007 (3)0.002 (3)
C70.044 (3)0.043 (3)0.040 (3)0.006 (3)0.001 (3)0.004 (2)
C80.053 (4)0.041 (3)0.044 (3)0.009 (3)0.001 (3)0.002 (3)
C90.051 (4)0.048 (4)0.039 (3)0.011 (3)0.001 (3)0.004 (3)
C100.058 (4)0.058 (4)0.056 (4)0.018 (3)0.011 (3)0.006 (3)
C110.091 (5)0.054 (4)0.048 (4)0.017 (4)0.017 (4)0.003 (3)
C120.089 (6)0.055 (4)0.065 (4)0.002 (4)0.011 (4)0.010 (4)
C130.065 (4)0.049 (4)0.067 (4)0.001 (3)0.003 (4)0.003 (3)
Hg10.0463 (2)0.0654 (3)0.0506 (2)0.0000.00860 (14)0.000
I10.1231 (5)0.1306 (6)0.0804 (4)0.0764 (4)0.0547 (3)0.0385 (4)
N10.042 (3)0.072 (4)0.048 (3)0.009 (3)0.000 (2)0.001 (3)
N20.036 (3)0.047 (3)0.048 (3)0.002 (2)0.005 (2)0.004 (2)
N30.038 (3)0.049 (3)0.054 (3)0.008 (2)0.004 (2)0.002 (2)
Geometric parameters (Å, º) top
C1—N11.317 (7)C8—N21.380 (7)
C1—C21.373 (8)C8—C131.389 (8)
C1—H10.9300C8—C91.392 (8)
C2—C31.372 (8)C9—N31.384 (7)
C2—H20.9300C9—C101.404 (8)
C3—C41.365 (8)C10—C111.374 (9)
C3—C61.523 (7)C10—H100.9300
C4—C51.371 (8)C11—C121.385 (9)
C4—H40.9300C11—H110.9300
C5—N11.315 (7)C12—C131.370 (8)
C5—H50.9300C12—H120.9300
C6—N21.459 (6)C13—H130.9300
C6—H6A0.9700Hg1—N1ii2.416 (5)
C6—H6B0.9700Hg1—N12.416 (5)
C7—N31.321 (7)Hg1—I1ii2.6349 (8)
C7—N21.384 (7)Hg1—I12.6349 (8)
C7—C7i1.447 (11)
N1—C1—C2123.6 (6)N3—C9—C10129.2 (6)
N1—C1—H1118.2C8—C9—C10120.5 (6)
C2—C1—H1118.2C11—C10—C9116.9 (6)
C3—C2—C1119.2 (6)C11—C10—H10121.6
C3—C2—H2120.4C9—C10—H10121.6
C1—C2—H2120.4C10—C11—C12121.9 (6)
C4—C3—C2117.3 (5)C10—C11—H11119.1
C4—C3—C6122.7 (5)C12—C11—H11119.1
C2—C3—C6120.0 (5)C13—C12—C11122.1 (6)
C3—C4—C5119.3 (6)C13—C12—H12119.0
C3—C4—H4120.3C11—C12—H12119.0
C5—C4—H4120.3C12—C13—C8116.8 (6)
N1—C5—C4123.8 (6)C12—C13—H13121.6
N1—C5—H5118.1C8—C13—H13121.6
C4—C5—H5118.1N1ii—Hg1—N193.4 (2)
N2—C6—C3113.8 (5)N1ii—Hg1—I1ii98.24 (12)
N2—C6—H6A108.8N1—Hg1—I1ii106.80 (12)
C3—C6—H6A108.8N1ii—Hg1—I1106.80 (12)
N2—C6—H6B108.8N1—Hg1—I198.24 (12)
C3—C6—H6B108.8I1ii—Hg1—I1143.27 (4)
H6A—C6—H6B107.7C5—N1—C1116.7 (5)
N3—C7—N2113.0 (5)C5—N1—Hg1121.6 (4)
N3—C7—C7i124.2 (7)C1—N1—Hg1121.5 (4)
N2—C7—C7i122.8 (6)C8—N2—C7105.8 (4)
N2—C8—C13132.1 (6)C8—N2—C6125.1 (5)
N2—C8—C9106.1 (5)C7—N2—C6129.1 (5)
C13—C8—C9121.8 (6)C7—N3—C9104.8 (5)
N3—C9—C8110.3 (5)
N1—C1—C2—C31.6 (12)C2—C1—N1—Hg1175.5 (6)
C1—C2—C3—C41.8 (10)N1ii—Hg1—N1—C564.5 (5)
C1—C2—C3—C6178.9 (6)I1ii—Hg1—N1—C535.2 (5)
C2—C3—C4—C50.8 (10)I1—Hg1—N1—C5172.0 (5)
C6—C3—C4—C5180.0 (6)N1ii—Hg1—N1—C1120.2 (6)
C3—C4—C5—N10.7 (10)I1ii—Hg1—N1—C1140.2 (5)
C4—C3—C6—N245.1 (8)I1—Hg1—N1—C112.6 (5)
C2—C3—C6—N2134.1 (6)C13—C8—N2—C7179.3 (6)
N2—C8—C9—N30.5 (6)C9—C8—N2—C70.7 (6)
C13—C8—C9—N3179.5 (5)C13—C8—N2—C63.0 (9)
N2—C8—C9—C10179.0 (5)C9—C8—N2—C6177.1 (5)
C13—C8—C9—C101.0 (9)N3—C7—N2—C80.7 (6)
N3—C9—C10—C11178.9 (6)C7i—C7—N2—C8179.8 (6)
C8—C9—C10—C110.5 (8)N3—C7—N2—C6176.9 (5)
C9—C10—C11—C121.4 (9)C7i—C7—N2—C62.2 (10)
C10—C11—C12—C130.8 (10)C3—C6—N2—C897.9 (6)
C11—C12—C13—C80.7 (10)C3—C6—N2—C784.8 (7)
N2—C8—C13—C12178.4 (6)N2—C7—N3—C90.5 (6)
C9—C8—C13—C121.6 (9)C7i—C7—N3—C9179.5 (6)
C4—C5—N1—C11.0 (10)C8—C9—N3—C70.0 (6)
C4—C5—N1—Hg1176.6 (5)C10—C9—N3—C7179.4 (5)
C2—C1—N1—C50.1 (11)
Symmetry codes: (i) x+1/2, y+1/2, z+2; (ii) x, y, z+3/2.
C—H···X interaction parameters (Å, °) for (II), (III) and (IV) top
D—H···AH···AD···AD—H···A
C12—H12···Cl1v2.863.555 (6)132
C2—H2···Br1iii3.083.875 (6)145
C2—H2···I1iii3.193.998 (7)147
Symmetry codes: (iii) -x, -y+1, -z+2; (v) x, -y, z+1/2.
 

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