Three one-dimensional coordination polymers based on 1,1′-bis­(pyridin-4-ylmeth­yl)-2,2′-bi-1H-benzimidazole and HgX₂ (X = Cl, Br and I)

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 Hg^II coordination complexes, (II)–(IV), have one-dimensional zigzag chains composed of L and HgX₂ (X = Cl, Br and I), and the Hg^II 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.

Computing details

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

Crystal data

C26H20N6	Z = 2
Mr = 416.48	F(000) = 436
Triclinic, P1	Dx = 1.348 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.094 (4) Å	Cell parameters from 1073 reflections
b = 10.183 (4) Å	θ = 2.4–22.6°
c = 10.972 (4) Å	µ = 0.08 mm^−1
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) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3762 independent reflections
Radiation source: fine-focus sealed tube	2341 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
phi and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→12
Tmin = 0.986, Tmax = 0.992	k = −12→8
5451 measured reflections	l = −10→13

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0943P)^2] where P = (Fo^2 + 2Fc^2)/3
3762 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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
C1	0.4589 (4)	−0.0172 (4)	0.1635 (4)	0.0661 (10)
H1	0.4161	−0.1078	0.1552	0.079*
C2	0.3778 (4)	0.0619 (3)	0.1108 (3)	0.0568 (9)
H2	0.2827	0.0254	0.0703	0.068*
C3	0.4378 (3)	0.1945 (3)	0.1182 (3)	0.0427 (7)
C4	0.5782 (3)	0.2430 (3)	0.1807 (3)	0.0535 (9)
H4	0.6240	0.3325	0.1887	0.064*
C5	0.6503 (4)	0.1551 (4)	0.2316 (3)	0.0600 (9)
H5	0.7455	0.1890	0.2733	0.072*
C6	0.3519 (3)	0.2804 (3)	0.0548 (3)	0.0503 (8)
H6A	0.3428	0.2499	−0.0394	0.060*
H6B	0.2590	0.2622	0.0656	0.060*
C7	0.4875 (3)	0.5212 (3)	0.0652 (3)	0.0414 (7)
C8	0.4107 (3)	0.5116 (3)	0.2359 (3)	0.0446 (8)
C9	0.4877 (3)	0.6449 (3)	0.2585 (3)	0.0468 (8)
C10	0.5095 (4)	0.7521 (4)	0.3783 (3)	0.0604 (9)
H10	0.5604	0.8422	0.3948	0.072*
C11	0.4526 (4)	0.7180 (4)	0.4694 (4)	0.0660 (10)
H11	0.4671	0.7864	0.5508	0.079*
C12	0.3733 (4)	0.5841 (4)	0.4454 (4)	0.0637 (10)
H12	0.3338	0.5668	0.5097	0.076*
C13	0.3525 (3)	0.4777 (4)	0.3292 (3)	0.0551 (9)
H13	0.3020	0.3876	0.3135	0.066*
C14	0.0140 (3)	0.5264 (3)	0.5713 (3)	0.0413 (7)
C15	0.0878 (3)	0.5416 (3)	0.7811 (3)	0.0456 (8)
C16	0.0232 (3)	0.6517 (3)	0.7687 (3)	0.0473 (8)
C17	0.0148 (4)	0.7520 (4)	0.8792 (4)	0.0612 (10)
H17	−0.0283	0.8252	0.8715	0.073*
C18	0.0719 (4)	0.7413 (4)	1.0015 (4)	0.0678 (11)
H18	0.0675	0.8079	1.0776	0.081*
C19	0.1369 (4)	0.6304 (4)	1.0125 (4)	0.0678 (11)
H19	0.1758	0.6259	1.0962	0.081*
C20	0.1445 (3)	0.5300 (4)	0.9045 (3)	0.0580 (9)
H20	0.1861	0.4560	0.9126	0.070*
C21	0.1332 (3)	0.3328 (3)	0.6268 (3)	0.0511 (8)
H21A	0.2264	0.3508	0.6857	0.061*
H21B	0.1399	0.3066	0.5367	0.061*
C22	0.0419 (3)	0.2130 (3)	0.6430 (3)	0.0448 (8)
C23	−0.1013 (3)	0.1973 (4)	0.6203 (3)	0.0555 (9)
H23	−0.1450	0.2643	0.5966	0.067*
C24	−0.1775 (4)	0.0819 (4)	0.6332 (4)	0.0681 (11)
H24	−0.2732	0.0739	0.6181	0.082*
C25	0.0122 (5)	−0.0037 (4)	0.6856 (4)	0.0721 (11)
H25	0.0527	−0.0737	0.7067	0.087*
C26	0.0983 (4)	0.1086 (3)	0.6771 (3)	0.0538 (9)
H26	0.1939	0.1143	0.6942	0.065*
N1	0.5940 (3)	0.0277 (3)	0.2252 (3)	0.0631 (8)
N2	0.4121 (3)	0.4319 (2)	0.1107 (2)	0.0440 (6)
N3	0.5341 (3)	0.6494 (3)	0.1504 (2)	0.0491 (7)
N4	−0.0216 (3)	0.6393 (3)	0.6362 (2)	0.0480 (7)
N5	0.0810 (3)	0.4621 (2)	0.6554 (2)	0.0454 (7)
N6	−0.1243 (4)	−0.0196 (3)	0.6660 (3)	0.0762 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.070 (3)	0.042 (2)	0.083 (3)	0.0096 (19)	0.016 (2)	0.0215 (19)
C2	0.045 (2)	0.045 (2)	0.075 (2)	0.0044 (16)	0.0062 (17)	0.0237 (18)
C3	0.0409 (18)	0.0437 (18)	0.0431 (17)	0.0078 (15)	0.0110 (13)	0.0152 (14)
C4	0.045 (2)	0.0462 (19)	0.068 (2)	0.0060 (16)	0.0105 (16)	0.0233 (17)
C5	0.043 (2)	0.062 (2)	0.078 (3)	0.0157 (18)	0.0138 (17)	0.027 (2)
C6	0.0442 (19)	0.0454 (19)	0.0529 (19)	0.0010 (15)	−0.0001 (14)	0.0190 (16)
C7	0.0342 (16)	0.0380 (17)	0.0506 (17)	0.0125 (14)	0.0018 (13)	0.0182 (15)
C8	0.0327 (16)	0.0485 (19)	0.057 (2)	0.0176 (15)	0.0050 (14)	0.0255 (16)
C9	0.0360 (17)	0.051 (2)	0.055 (2)	0.0221 (15)	0.0066 (14)	0.0187 (16)
C10	0.061 (2)	0.052 (2)	0.063 (2)	0.0231 (18)	0.0131 (18)	0.0111 (18)
C11	0.062 (2)	0.079 (3)	0.053 (2)	0.032 (2)	0.0117 (18)	0.011 (2)
C12	0.053 (2)	0.083 (3)	0.059 (2)	0.028 (2)	0.0145 (17)	0.026 (2)
C13	0.0417 (19)	0.063 (2)	0.068 (2)	0.0195 (17)	0.0081 (16)	0.0338 (19)
C14	0.0355 (17)	0.0366 (16)	0.0543 (17)	0.0120 (14)	0.0063 (14)	0.0220 (15)
C15	0.0358 (17)	0.0479 (19)	0.052 (2)	0.0072 (15)	0.0065 (14)	0.0210 (16)
C16	0.0427 (18)	0.0427 (18)	0.053 (2)	0.0018 (15)	0.0116 (14)	0.0156 (16)
C17	0.062 (2)	0.052 (2)	0.068 (2)	0.0067 (18)	0.0186 (19)	0.0195 (19)
C18	0.069 (3)	0.069 (3)	0.057 (2)	0.004 (2)	0.0188 (19)	0.013 (2)
C19	0.059 (2)	0.083 (3)	0.054 (2)	0.003 (2)	0.0057 (17)	0.025 (2)
C20	0.044 (2)	0.072 (2)	0.058 (2)	0.0114 (18)	0.0055 (16)	0.0310 (19)
C21	0.0426 (19)	0.056 (2)	0.063 (2)	0.0263 (16)	0.0109 (15)	0.0278 (17)
C22	0.0495 (19)	0.0436 (18)	0.0411 (17)	0.0201 (15)	0.0067 (14)	0.0135 (14)
C23	0.047 (2)	0.052 (2)	0.066 (2)	0.0186 (17)	0.0061 (16)	0.0213 (17)
C24	0.058 (2)	0.059 (2)	0.083 (3)	0.014 (2)	0.020 (2)	0.017 (2)
C25	0.093 (3)	0.052 (2)	0.092 (3)	0.037 (2)	0.038 (2)	0.034 (2)
C26	0.060 (2)	0.050 (2)	0.059 (2)	0.0294 (18)	0.0170 (16)	0.0211 (17)
N1	0.062 (2)	0.0549 (19)	0.078 (2)	0.0198 (16)	0.0182 (16)	0.0281 (16)
N2	0.0424 (15)	0.0386 (14)	0.0480 (15)	0.0101 (12)	0.0032 (11)	0.0167 (12)
N3	0.0462 (16)	0.0450 (16)	0.0546 (17)	0.0136 (13)	0.0069 (13)	0.0182 (14)
N4	0.0518 (17)	0.0404 (15)	0.0551 (17)	0.0143 (13)	0.0117 (13)	0.0214 (13)
N5	0.0400 (15)	0.0429 (15)	0.0556 (17)	0.0157 (12)	0.0072 (12)	0.0217 (13)
N6	0.088 (3)	0.053 (2)	0.099 (3)	0.0219 (19)	0.039 (2)	0.0302 (18)

Geometric parameters (Å, º)

C1—N1	1.323 (4)	C14—N4	1.317 (4)
C1—C2	1.376 (5)	C14—N5	1.387 (4)
C1—H1	0.9300	C14—C14^ii	1.448 (6)
C2—C3	1.369 (4)	C15—N5	1.369 (4)
C2—H2	0.9300	C15—C20	1.390 (4)
C3—C4	1.372 (4)	C15—C16	1.399 (4)
C3—C6	1.513 (4)	C16—C17	1.377 (4)
C4—C5	1.389 (5)	C16—N4	1.383 (4)
C4—H4	0.9300	C17—C18	1.376 (5)
C5—N1	1.314 (4)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.406 (5)
C6—N2	1.466 (4)	C18—H18	0.9300
C6—H6A	0.9700	C19—C20	1.355 (5)
C6—H6B	0.9700	C19—H19	0.9300
C7—N3	1.316 (4)	C20—H20	0.9300
C7—N2	1.372 (4)	C21—N5	1.468 (4)
C7—C7^i	1.464 (6)	C21—C22	1.495 (4)
C8—C9	1.386 (4)	C21—H21A	0.9700
C8—C13	1.388 (4)	C21—H21B	0.9700
C8—N2	1.389 (4)	C22—C26	1.378 (4)
C9—N3	1.380 (4)	C22—C23	1.387 (4)
C9—C10	1.399 (4)	C23—C24	1.368 (5)
C10—C11	1.360 (5)	C23—H23	0.9300
C10—H10	0.9300	C24—N6	1.330 (5)
C11—C12	1.397 (5)	C24—H24	0.9300
C11—H11	0.9300	C25—N6	1.324 (5)
C12—C13	1.370 (5)	C25—C26	1.370 (5)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
N1—C1—C2	124.1 (3)	C20—C15—C16	121.3 (3)
N1—C1—H1	118.0	C17—C16—N4	130.2 (3)
C2—C1—H1	118.0	C17—C16—C15	120.5 (3)
C3—C2—C1	119.6 (3)	N4—C16—C15	109.3 (3)
C3—C2—H2	120.2	C18—C17—C16	118.2 (4)
C1—C2—H2	120.2	C18—C17—H17	120.9
C2—C3—C4	117.4 (3)	C16—C17—H17	120.9
C2—C3—C6	120.4 (3)	C17—C18—C19	120.6 (3)
C4—C3—C6	122.1 (3)	C17—C18—H18	119.7
C3—C4—C5	118.4 (3)	C19—C18—H18	119.7
C3—C4—H4	120.8	C20—C19—C18	121.8 (4)
C5—C4—H4	120.8	C20—C19—H19	119.1
N1—C5—C4	124.8 (3)	C18—C19—H19	119.1
N1—C5—H5	117.6	C19—C20—C15	117.5 (4)
C4—C5—H5	117.6	C19—C20—H20	121.2
N2—C6—C3	113.4 (2)	C15—C20—H20	121.2
N2—C6—H6A	108.9	N5—C21—C22	112.8 (2)
C3—C6—H6A	108.9	N5—C21—H21A	109.0
N2—C6—H6B	108.9	C22—C21—H21A	109.0
C3—C6—H6B	108.9	N5—C21—H21B	109.0
H6A—C6—H6B	107.7	C22—C21—H21B	109.0
N3—C7—N2	113.0 (3)	H21A—C21—H21B	107.8
N3—C7—C7^i	123.4 (3)	C26—C22—C23	116.7 (3)
N2—C7—C7^i	123.6 (3)	C26—C22—C21	120.1 (3)
C9—C8—C13	122.5 (3)	C23—C22—C21	123.1 (3)
C9—C8—N2	105.6 (3)	C24—C23—C22	119.2 (3)
C13—C8—N2	132.0 (3)	C24—C23—H23	120.4
N3—C9—C8	110.5 (3)	C22—C23—H23	120.4
N3—C9—C10	129.0 (3)	N6—C24—C23	124.7 (4)
C8—C9—C10	120.5 (3)	N6—C24—H24	117.7
C11—C10—C9	116.7 (3)	C23—C24—H24	117.7
C11—C10—H10	121.6	N6—C25—C26	124.8 (3)
C9—C10—H10	121.6	N6—C25—H25	117.6
C10—C11—C12	122.5 (3)	C26—C25—H25	117.6
C10—C11—H11	118.7	C25—C26—C22	119.4 (3)
C12—C11—H11	118.7	C25—C26—H26	120.3
C13—C12—C11	121.4 (3)	C22—C26—H26	120.3
C13—C12—H12	119.3	C5—N1—C1	115.6 (3)
C11—C12—H12	119.3	C7—N2—C8	106.0 (2)
C12—C13—C8	116.4 (3)	C7—N2—C6	131.4 (3)
C12—C13—H13	121.8	C8—N2—C6	122.4 (3)
C8—C13—H13	121.8	C7—N3—C9	105.0 (3)
N4—C14—N5	112.1 (3)	C14—N4—C16	105.8 (3)
N4—C14—C14^ii	124.4 (3)	C15—N5—C14	106.3 (3)
N5—C14—C14^ii	123.4 (3)	C15—N5—C21	122.8 (3)
N5—C15—C20	132.3 (3)	C14—N5—C21	130.8 (3)
N5—C15—C16	106.5 (3)	C25—N6—C24	115.3 (3)
N1—C1—C2—C3	1.5 (6)	N6—C25—C26—C22	−1.5 (6)
C1—C2—C3—C4	−0.8 (5)	C23—C22—C26—C25	0.6 (5)
C1—C2—C3—C6	176.9 (3)	C21—C22—C26—C25	−177.1 (3)
C2—C3—C4—C5	0.2 (5)	C4—C5—N1—C1	0.9 (5)
C6—C3—C4—C5	−177.5 (3)	C2—C1—N1—C5	−1.5 (6)
C3—C4—C5—N1	−0.3 (5)	N3—C7—N2—C8	0.3 (3)
C2—C3—C6—N2	158.5 (3)	C7^i—C7—N2—C8	−179.1 (3)
C4—C3—C6—N2	−23.9 (4)	N3—C7—N2—C6	−174.3 (3)
C13—C8—C9—N3	179.5 (3)	C7^i—C7—N2—C6	6.3 (5)
N2—C8—C9—N3	0.9 (3)	C9—C8—N2—C7	−0.7 (3)
C13—C8—C9—C10	−0.2 (5)	C13—C8—N2—C7	−179.1 (3)
N2—C8—C9—C10	−178.8 (3)	C9—C8—N2—C6	174.5 (2)
N3—C9—C10—C11	−179.2 (3)	C13—C8—N2—C6	−4.0 (5)
C8—C9—C10—C11	0.4 (5)	C3—C6—N2—C7	101.2 (3)
C9—C10—C11—C12	−1.4 (5)	C3—C6—N2—C8	−72.6 (4)
C10—C11—C12—C13	2.2 (5)	N2—C7—N3—C9	0.3 (3)
C11—C12—C13—C8	−1.9 (5)	C7^i—C7—N3—C9	179.7 (3)
C9—C8—C13—C12	0.9 (5)	C8—C9—N3—C7	−0.8 (3)
N2—C8—C13—C12	179.1 (3)	C10—C9—N3—C7	178.9 (3)
N5—C15—C16—C17	−179.1 (3)	N5—C14—N4—C16	0.1 (3)
C20—C15—C16—C17	0.3 (5)	C14^ii—C14—N4—C16	179.6 (3)
N5—C15—C16—N4	−0.4 (3)	C17—C16—N4—C14	178.8 (3)
C20—C15—C16—N4	179.0 (3)	C15—C16—N4—C14	0.2 (3)
N4—C16—C17—C18	−178.2 (3)	C20—C15—N5—C14	−178.9 (3)
C15—C16—C17—C18	0.2 (5)	C16—C15—N5—C14	0.4 (3)
C16—C17—C18—C19	0.0 (5)	C20—C15—N5—C21	3.2 (5)
C17—C18—C19—C20	−0.8 (6)	C16—C15—N5—C21	−177.5 (3)
C18—C19—C20—C15	1.2 (5)	N4—C14—N5—C15	−0.4 (3)
N5—C15—C20—C19	178.3 (3)	C14^ii—C14—N5—C15	−179.9 (3)
C16—C15—C20—C19	−1.0 (5)	N4—C14—N5—C21	177.3 (3)
N5—C21—C22—C26	−151.8 (3)	C14^ii—C14—N5—C21	−2.2 (6)
N5—C21—C22—C23	30.8 (4)	C22—C21—N5—C15	72.9 (4)
C26—C22—C23—C24	0.3 (5)	C22—C21—N5—C14	−104.5 (3)
C21—C22—C23—C24	177.8 (3)	C26—C25—N6—C24	1.4 (6)
C22—C23—C24—N6	−0.4 (6)	C23—C24—N6—C25	−0.4 (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]

Crystal data

[HgCl2(C26H20N6)]	F(000) = 1328
Mr = 687.97	Dx = 1.862 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 2207 reflections
a = 29.641 (15) Å	θ = 2.8–24.7°
b = 4.953 (2) Å	µ = 6.52 mm^−1
c = 16.932 (8) Å	T = 298 K
β = 99.236 (11)°	Plan, colourless
V = 2454 (2) Å^3	0.20 × 0.10 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2293 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
phi and ω scans	θmax = 25.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −36→29
Tmin = 0.356, Tmax = 0.781	k = −6→5
6064 measured reflections	l = −19→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.033P)^2] where P = (Fo^2 + 2Fc^2)/3
2293 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 1.06 e Å^−3
0 restraints	Δρmin = −0.75 e Å^−3

Special details

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
C1	0.04608 (19)	0.6141 (13)	0.3915 (4)	0.0735 (17)
H1	0.0153	0.6350	0.3954	0.088*
C2	0.0770 (2)	0.7553 (10)	0.4436 (4)	0.0680 (16)
H2	0.0672	0.8723	0.4804	0.082*
C3	0.12272 (17)	0.7234 (9)	0.4415 (3)	0.0444 (12)
C4	0.13442 (16)	0.5511 (11)	0.3852 (3)	0.0565 (13)
H4	0.1650	0.5216	0.3816	0.068*
C5	0.10072 (19)	0.4217 (13)	0.3341 (3)	0.0654 (15)
H5	0.1095	0.3071	0.2958	0.078*
C6	0.15835 (16)	0.8771 (9)	0.4984 (3)	0.0478 (12)
H6A	0.1718	1.0157	0.4691	0.057*
H6B	0.1438	0.9652	0.5389	0.057*
C7	0.23906 (17)	0.6681 (9)	0.5277 (2)	0.0403 (10)
C8	0.18701 (16)	0.5128 (9)	0.5949 (2)	0.0423 (11)
C9	0.22823 (17)	0.3793 (9)	0.6164 (3)	0.0442 (12)
C10	0.2318 (2)	0.1755 (10)	0.6743 (3)	0.0541 (13)
H10	0.2590	0.0818	0.6897	0.065*
C11	0.1939 (2)	0.1202 (11)	0.7073 (3)	0.0604 (15)
H11	0.1953	−0.0150	0.7457	0.072*
C12	0.1531 (2)	0.2589 (10)	0.6854 (3)	0.0577 (15)
H12	0.1281	0.2143	0.7097	0.069*
C13	0.14858 (17)	0.4585 (11)	0.6292 (3)	0.0524 (12)
H13	0.1214	0.5525	0.6148	0.063*
Cl1	0.04580 (5)	0.0778 (4)	0.15364 (10)	0.0924 (5)
Hg1	0.0000	0.19383 (7)	0.2500	0.07134 (16)
N1	0.05643 (14)	0.4501 (10)	0.3360 (2)	0.0566 (11)
N2	0.19419 (14)	0.6973 (7)	0.5371 (2)	0.0426 (9)
N3	0.26075 (13)	0.4803 (8)	0.5749 (2)	0.0458 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.030 (3)	0.091 (5)	0.095 (4)	0.013 (3)	−0.001 (3)	−0.006 (4)
C2	0.046 (4)	0.078 (4)	0.080 (4)	0.015 (3)	0.007 (3)	−0.021 (3)
C3	0.042 (3)	0.047 (3)	0.043 (3)	0.006 (2)	0.003 (2)	0.009 (2)
C4	0.032 (3)	0.083 (4)	0.054 (3)	−0.001 (3)	0.009 (2)	−0.015 (3)
C5	0.050 (4)	0.092 (4)	0.054 (3)	−0.001 (3)	0.008 (3)	−0.017 (3)
C6	0.047 (3)	0.039 (3)	0.056 (3)	0.005 (2)	0.003 (2)	−0.001 (2)
C7	0.046 (3)	0.037 (3)	0.036 (2)	−0.003 (2)	0.001 (2)	−0.009 (2)
C8	0.051 (3)	0.040 (3)	0.035 (2)	−0.006 (2)	0.002 (2)	−0.010 (2)
C9	0.052 (3)	0.037 (3)	0.040 (2)	−0.006 (2)	−0.001 (2)	−0.004 (2)
C10	0.062 (4)	0.048 (3)	0.049 (3)	−0.001 (3)	−0.002 (3)	0.004 (3)
C11	0.075 (4)	0.055 (4)	0.049 (3)	−0.012 (3)	0.001 (3)	0.004 (2)
C12	0.064 (4)	0.061 (4)	0.051 (3)	−0.019 (3)	0.015 (3)	−0.007 (3)
C13	0.052 (3)	0.051 (3)	0.053 (3)	−0.005 (3)	0.008 (2)	−0.008 (3)
Cl1	0.0523 (10)	0.1269 (14)	0.0996 (11)	−0.0066 (9)	0.0175 (8)	−0.0222 (11)
Hg1	0.0383 (2)	0.1028 (3)	0.0689 (2)	0.000	−0.00357 (14)	0.000
N1	0.037 (2)	0.076 (3)	0.054 (2)	0.002 (2)	−0.0026 (19)	0.000 (2)
N2	0.044 (2)	0.039 (2)	0.042 (2)	−0.0003 (19)	−0.0011 (17)	−0.0023 (18)
N3	0.045 (2)	0.047 (3)	0.042 (2)	−0.001 (2)	−0.0022 (18)	0.0004 (19)

Geometric parameters (Å, º)

C1—N1	1.316 (7)	C8—N2	1.380 (6)
C1—C2	1.359 (8)	C8—C9	1.386 (6)
C1—H1	0.9300	C8—C13	1.386 (6)
C2—C3	1.371 (7)	C9—N3	1.374 (6)
C2—H2	0.9300	C9—C10	1.400 (7)
C3—C4	1.365 (7)	C10—C11	1.361 (8)
C3—C6	1.516 (7)	C10—H10	0.9300
C4—C5	1.371 (7)	C11—C12	1.388 (8)
C4—H4	0.9300	C11—H11	0.9300
C5—N1	1.326 (6)	C12—C13	1.363 (7)
C5—H5	0.9300	C12—H12	0.9300
C6—N2	1.458 (6)	C13—H13	0.9300
C6—H6A	0.9700	Hg1—N1	2.397 (4)
C6—H6B	0.9700	Hg1—N1^ii	2.397 (4)
C7—N3	1.324 (5)	Hg1—Cl1	2.3553 (18)
C7—N2	1.372 (6)	Hg1—Cl1^ii	2.3553 (18)
C7—C7^i	1.468 (10)
N1—C1—C2	124.9 (5)	N3—C9—C10	129.8 (5)
N1—C1—H1	117.6	C8—C9—C10	119.5 (5)
C2—C1—H1	117.6	C11—C10—C9	117.2 (5)
C1—C2—C3	119.3 (5)	C11—C10—H10	121.4
C1—C2—H2	120.3	C9—C10—H10	121.4
C3—C2—H2	120.3	C10—C11—C12	122.2 (5)
C4—C3—C2	117.0 (5)	C10—C11—H11	118.9
C4—C3—C6	122.0 (4)	C12—C11—H11	118.9
C2—C3—C6	121.1 (4)	C13—C12—C11	122.0 (5)
C3—C4—C5	119.5 (5)	C13—C12—H12	119.0
C3—C4—H4	120.3	C11—C12—H12	119.0
C5—C4—H4	120.3	C12—C13—C8	116.0 (5)
N1—C5—C4	124.0 (5)	C12—C13—H13	122.0
N1—C5—H5	118.0	C8—C13—H13	122.0
C4—C5—H5	118.0	N1—Hg1—N1^ii	116.0 (2)
N2—C6—C3	111.2 (4)	Cl1—Hg1—N1	97.25 (12)
N2—C6—H6A	109.4	Cl1^ii—Hg1—N1	97.60 (11)
C3—C6—H6A	109.4	Cl1—Hg1—N1^ii	97.60 (11)
N2—C6—H6B	109.4	Cl1^ii—Hg1—N1^ii	97.25 (12)
C3—C6—H6B	109.4	Cl1—Hg1—Cl1^ii	151.74 (10)
H6A—C6—H6B	108.0	C1—N1—C5	115.3 (4)
N3—C7—N2	112.9 (4)	C1—N1—Hg1	122.7 (3)
N3—C7—C7^i	123.5 (6)	C5—N1—Hg1	121.8 (4)
N2—C7—C7^i	123.5 (5)	C7—N2—C8	106.0 (4)
N2—C8—C9	105.8 (4)	C7—N2—C6	131.5 (4)
N2—C8—C13	131.1 (5)	C8—N2—C6	122.6 (4)
C9—C8—C13	123.1 (5)	C7—N3—C9	104.6 (4)
N3—C9—C8	110.7 (4)
N1—C1—C2—C3	−2.1 (9)	C4—C5—N1—Hg1	−175.9 (4)
C1—C2—C3—C4	0.9 (8)	Cl1—Hg1—N1—C1	164.5 (4)
C1—C2—C3—C6	179.9 (5)	Cl1^ii—Hg1—N1—C1	−39.6 (4)
C2—C3—C4—C5	0.4 (8)	N1^ii—Hg1—N1—C1	62.4 (4)
C6—C3—C4—C5	−178.6 (5)	Cl1—Hg1—N1—C5	−20.1 (4)
C3—C4—C5—N1	−0.8 (9)	Cl1^ii—Hg1—N1—C5	135.8 (4)
C4—C3—C6—N2	−50.0 (6)	N1^ii—Hg1—N1—C5	−122.3 (4)
C2—C3—C6—N2	131.0 (5)	N3—C7—N2—C8	−0.1 (5)
N2—C8—C9—N3	1.3 (5)	C7^i—C7—N2—C8	−178.9 (5)
C13—C8—C9—N3	−177.8 (4)	N3—C7—N2—C6	179.7 (4)
N2—C8—C9—C10	−179.6 (4)	C7^i—C7—N2—C6	0.9 (8)
C13—C8—C9—C10	1.3 (7)	C9—C8—N2—C7	−0.8 (4)
N3—C9—C10—C11	178.5 (4)	C13—C8—N2—C7	178.3 (4)
C8—C9—C10—C11	−0.4 (7)	C9—C8—N2—C6	179.4 (4)
C9—C10—C11—C12	−0.3 (8)	C13—C8—N2—C6	−1.5 (7)
C10—C11—C12—C13	0.3 (8)	C3—C6—N2—C7	108.6 (5)
C11—C12—C13—C8	0.5 (7)	C3—C6—N2—C8	−71.6 (5)
N2—C8—C13—C12	179.8 (4)	N2—C7—N3—C9	0.9 (5)
C9—C8—C13—C12	−1.3 (7)	C7^i—C7—N3—C9	179.7 (5)
C2—C1—N1—C5	1.7 (9)	C8—C9—N3—C7	−1.4 (5)
C2—C1—N1—Hg1	177.3 (5)	C10—C9—N3—C7	179.7 (4)
C4—C5—N1—C1	−0.2 (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]

Crystal data

[HgBr2(C26H20N6)]	F(000) = 1472
Mr = 776.89	Dx = 2.037 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c2yc	Cell parameters from 3227 reflections
a = 24.494 (8) Å	θ = 2.4–25.9°
b = 6.006 (2) Å	µ = 9.26 mm^−1
c = 17.306 (6) Å	T = 298 K
β = 95.796 (4)°	Block, colourless
V = 2532.8 (15) Å^3	0.23 × 0.18 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2387 independent reflections
Radiation source: fine-focus sealed tube	2101 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
phi and ω scans	θmax = 25.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −29→22
Tmin = 0.225, Tmax = 0.458	k = −5→7
6393 measured reflections	l = −21→20

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0537P)^2] where P = (Fo^2 + 2Fc^2)/3
2387 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 1.05 e Å^−3
0 restraints	Δρmin = −1.35 e Å^−3

Special details

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
C1	0.0507 (2)	0.5005 (10)	0.9059 (3)	0.0543 (15)
H1	0.0291	0.6031	0.9292	0.065*
C2	0.0822 (2)	0.3553 (10)	0.9522 (3)	0.0505 (14)
H2	0.0819	0.3599	1.0058	0.061*
C3	0.1150 (2)	0.2002 (8)	0.9183 (3)	0.0377 (11)
C4	0.1135 (2)	0.2007 (9)	0.8392 (3)	0.0462 (13)
H4	0.1346	0.0994	0.8144	0.055*
C5	0.0808 (3)	0.3517 (10)	0.7964 (3)	0.0513 (14)
H5	0.0805	0.3497	0.7426	0.062*
C6	0.1503 (2)	0.0404 (8)	0.9690 (3)	0.0401 (11)
H6A	0.1509	0.0872	1.0227	0.048*
H6B	0.1339	−0.1067	0.9646	0.048*
C7	0.2518 (2)	0.1531 (8)	0.9745 (3)	0.0353 (10)
C8	0.2264 (2)	−0.1381 (8)	0.9033 (3)	0.0371 (11)
C9	0.2823 (2)	−0.1007 (8)	0.9044 (3)	0.0385 (11)
C10	0.3151 (3)	−0.2426 (8)	0.8651 (3)	0.0463 (13)
H10	0.3527	−0.2192	0.8657	0.056*
C11	0.2895 (3)	−0.4189 (9)	0.8256 (3)	0.0534 (15)
H11	0.3103	−0.5175	0.7992	0.064*
C12	0.2334 (3)	−0.4529 (9)	0.8241 (3)	0.0542 (15)
H12	0.2176	−0.5731	0.7963	0.065*
C13	0.2000 (3)	−0.3131 (8)	0.8627 (3)	0.0486 (13)
H13	0.1623	−0.3354	0.8614	0.058*
Hg1	0.0000	0.77841 (5)	0.7500	0.04575 (14)
Br1	−0.05808 (4)	0.90727 (16)	0.84956 (4)	0.0981 (3)
N1	0.04965 (17)	0.5005 (8)	0.8282 (2)	0.0464 (11)
N2	0.20649 (16)	0.0267 (6)	0.9488 (2)	0.0353 (9)
N3	0.29770 (18)	0.0830 (6)	0.9497 (2)	0.0401 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.041 (3)	0.074 (4)	0.049 (3)	0.021 (3)	0.008 (3)	−0.004 (3)
C2	0.042 (3)	0.071 (3)	0.040 (3)	0.015 (3)	0.008 (2)	0.002 (2)
C3	0.024 (3)	0.043 (2)	0.046 (3)	−0.004 (2)	0.002 (2)	−0.001 (2)
C4	0.045 (3)	0.049 (3)	0.045 (3)	0.010 (2)	0.002 (2)	−0.012 (2)
C5	0.056 (4)	0.059 (3)	0.038 (3)	0.012 (3)	−0.003 (3)	−0.007 (2)
C6	0.033 (3)	0.041 (2)	0.047 (3)	−0.001 (2)	0.008 (2)	0.003 (2)
C7	0.032 (3)	0.039 (2)	0.034 (2)	0.005 (2)	0.000 (2)	0.0017 (19)
C8	0.039 (3)	0.037 (2)	0.035 (2)	0.005 (2)	0.000 (2)	0.0017 (19)
C9	0.044 (3)	0.040 (3)	0.031 (2)	0.011 (2)	0.001 (2)	0.0042 (19)
C10	0.045 (3)	0.051 (3)	0.045 (3)	0.014 (2)	0.011 (2)	0.006 (2)
C11	0.075 (5)	0.045 (3)	0.042 (3)	0.016 (3)	0.016 (3)	−0.002 (2)
C12	0.073 (5)	0.043 (3)	0.047 (3)	0.002 (3)	0.008 (3)	−0.009 (2)
C13	0.051 (4)	0.045 (3)	0.050 (3)	−0.003 (3)	0.006 (3)	−0.007 (2)
Hg1	0.0374 (2)	0.0554 (2)	0.04453 (19)	0.000	0.00467 (12)	0.000
Br1	0.1052 (7)	0.1223 (7)	0.0746 (5)	0.0701 (6)	0.0467 (4)	0.0372 (4)
N1	0.030 (3)	0.067 (3)	0.042 (2)	0.010 (2)	−0.0012 (19)	−0.007 (2)
N2	0.027 (2)	0.039 (2)	0.040 (2)	0.0041 (17)	0.0032 (17)	−0.0009 (16)
N3	0.034 (3)	0.043 (2)	0.044 (2)	0.0037 (19)	0.0030 (18)	−0.0030 (18)

Geometric parameters (Å, º)

C1—N1	1.343 (6)	C8—C9	1.385 (7)
C1—C2	1.370 (8)	C8—N2	1.385 (6)
C1—H1	0.9300	C8—C13	1.388 (8)
C2—C3	1.396 (8)	C9—N3	1.384 (6)
C2—H2	0.9300	C9—C10	1.394 (7)
C3—C4	1.365 (7)	C10—C11	1.377 (8)
C3—C6	1.513 (7)	C10—H10	0.9300
C4—C5	1.376 (8)	C11—C12	1.387 (9)
C4—H4	0.9300	C11—H11	0.9300
C5—N1	1.330 (7)	C12—C13	1.390 (8)
C5—H5	0.9300	C12—H12	0.9300
C6—N2	1.455 (6)	C13—H13	0.9300
C6—H6A	0.9700	Hg1—N1^ii	2.400 (4)
C6—H6B	0.9700	Hg1—N1	2.400 (4)
C7—N3	1.313 (6)	Hg1—Br1	2.4671 (9)
C7—N2	1.380 (6)	Hg1—Br1^ii	2.4671 (9)
C7—C7^i	1.470 (10)
N1—C1—C2	122.6 (5)	N3—C9—C10	128.7 (5)
N1—C1—H1	118.7	C8—C9—C10	120.8 (5)
C2—C1—H1	118.7	C11—C10—C9	117.1 (6)
C1—C2—C3	119.5 (5)	C11—C10—H10	121.4
C1—C2—H2	120.2	C9—C10—H10	121.4
C3—C2—H2	120.2	C10—C11—C12	121.5 (5)
C4—C3—C2	117.5 (5)	C10—C11—H11	119.2
C4—C3—C6	122.6 (5)	C12—C11—H11	119.2
C2—C3—C6	119.9 (5)	C11—C12—C13	122.2 (5)
C3—C4—C5	119.7 (5)	C11—C12—H12	118.9
C3—C4—H4	120.2	C13—C12—H12	118.9
C5—C4—H4	120.2	C8—C13—C12	115.7 (6)
N1—C5—C4	123.2 (5)	C8—C13—H13	122.2
N1—C5—H5	118.4	C12—C13—H13	122.2
C4—C5—H5	118.4	N1^ii—Hg1—N1	91.9 (2)
N2—C6—C3	113.4 (4)	N1^ii—Hg1—Br1	108.46 (11)
N2—C6—H6A	108.9	N1—Hg1—Br1	96.87 (10)
C3—C6—H6A	108.9	N1^ii—Hg1—Br1^ii	96.87 (10)
N2—C6—H6B	108.9	N1—Hg1—Br1^ii	108.46 (11)
C3—C6—H6B	108.9	Br1—Hg1—Br1^ii	143.43 (5)
H6A—C6—H6B	107.7	C5—N1—C1	117.4 (5)
N3—C7—N2	114.0 (4)	C5—N1—Hg1	120.9 (3)
N3—C7—C7^i	123.7 (6)	C1—N1—Hg1	121.5 (3)
N2—C7—C7^i	122.4 (6)	C7—N2—C8	104.9 (4)
C9—C8—N2	106.4 (4)	C7—N2—C6	129.8 (4)
C9—C8—C13	122.7 (5)	C8—N2—C6	125.0 (4)
N2—C8—C13	131.0 (5)	C7—N3—C9	104.3 (4)
N3—C9—C8	110.5 (4)
N1—C1—C2—C3	0.1 (10)	C2—C1—N1—Hg1	−174.5 (5)
C1—C2—C3—C4	−0.3 (9)	N1^ii—Hg1—N1—C5	59.3 (4)
C1—C2—C3—C6	179.5 (5)	Br1—Hg1—N1—C5	168.2 (4)
C2—C3—C4—C5	0.4 (8)	Br1^ii—Hg1—N1—C5	−38.6 (5)
C6—C3—C4—C5	−179.4 (5)	N1^ii—Hg1—N1—C1	−126.3 (5)
C3—C4—C5—N1	−0.2 (10)	Br1—Hg1—N1—C1	−17.4 (4)
C4—C3—C6—N2	47.3 (7)	Br1^ii—Hg1—N1—C1	135.9 (4)
C2—C3—C6—N2	−132.5 (5)	N3—C7—N2—C8	−0.2 (5)
N2—C8—C9—N3	0.2 (5)	C7^i—C7—N2—C8	−179.6 (5)
C13—C8—C9—N3	−179.5 (5)	N3—C7—N2—C6	174.1 (4)
N2—C8—C9—C10	178.4 (4)	C7^i—C7—N2—C6	−5.3 (9)
C13—C8—C9—C10	−1.3 (7)	C9—C8—N2—C7	0.0 (5)
N3—C9—C10—C11	178.1 (5)	C13—C8—N2—C7	179.7 (5)
C8—C9—C10—C11	0.3 (7)	C9—C8—N2—C6	−174.7 (4)
C9—C10—C11—C12	0.6 (8)	C13—C8—N2—C6	5.0 (8)
C10—C11—C12—C13	−0.6 (9)	C3—C6—N2—C7	88.2 (6)
C9—C8—C13—C12	1.3 (8)	C3—C6—N2—C8	−98.4 (5)
N2—C8—C13—C12	−178.3 (5)	N2—C7—N3—C9	0.3 (5)
C11—C12—C13—C8	−0.4 (8)	C7^i—C7—N3—C9	179.7 (6)
C4—C5—N1—C1	−0.1 (9)	C8—C9—N3—C7	−0.3 (5)
C4—C5—N1—Hg1	174.6 (5)	C10—C9—N3—C7	−178.4 (5)
C2—C1—N1—C5	0.1 (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]

Crystal data

[HgI2(C26H20N6)]	F(000) = 1616
Mr = 870.87	Dx = 2.156 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c2yc	Cell parameters from 2156 reflections
a = 25.339 (9) Å	θ = 2.6–21.8°
b = 6.056 (2) Å	µ = 8.06 mm^−1
c = 17.683 (6) Å	T = 298 K
β = 98.619 (4)°	Block, colourless
V = 2682.9 (16) Å^3	0.16 × 0.12 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	1950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
phi and ω scans	θmax = 25.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −25→30
Tmin = 0.359, Tmax = 0.531	k = −7→6
6723 measured reflections	l = −21→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0281P)^2] where P = (Fo^2 + 2Fc^2)/3
2526 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −1.19 e Å^−3

Special details

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
C1	0.0544 (3)	0.4861 (12)	0.9012 (4)	0.070 (2)
H1	0.0324	0.5807	0.9237	0.084*
C2	0.0866 (2)	0.3435 (13)	0.9476 (4)	0.070 (2)
H2	0.0868	0.3449	1.0002	0.084*
C3	0.1185 (2)	0.1987 (9)	0.9154 (3)	0.0445 (14)
C4	0.1174 (2)	0.2097 (10)	0.8381 (3)	0.0574 (17)
H4	0.1386	0.1161	0.8138	0.069*
C5	0.0846 (2)	0.3602 (11)	0.7965 (4)	0.0572 (16)
H5	0.0846	0.3664	0.7439	0.069*
C6	0.1538 (2)	0.0365 (10)	0.9658 (3)	0.0482 (14)
H6A	0.1549	0.0795	1.0189	0.058*
H6B	0.1378	−0.1092	0.9596	0.058*
C7	0.2517 (2)	0.1563 (9)	0.9751 (3)	0.0425 (13)
C8	0.2271 (2)	−0.1350 (10)	0.9037 (3)	0.0467 (14)
C9	0.2813 (2)	−0.0919 (10)	0.9059 (3)	0.0463 (14)
C10	0.3128 (3)	−0.2277 (10)	0.8663 (3)	0.0570 (16)
H10	0.3490	−0.2005	0.8669	0.068*
C11	0.2877 (3)	−0.4028 (11)	0.8267 (3)	0.0638 (18)
H11	0.3076	−0.4979	0.8008	0.077*
C12	0.2336 (3)	−0.4418 (11)	0.8242 (4)	0.0695 (19)
H12	0.2182	−0.5613	0.7961	0.083*
C13	0.2021 (3)	−0.3098 (10)	0.8619 (4)	0.0611 (17)
H13	0.1657	−0.3360	0.8595	0.073*
Hg1	0.0000	0.77000 (6)	0.7500	0.05394 (13)
I1	−0.05707 (3)	0.90708 (11)	0.85377 (3)	0.1074 (3)
N1	0.05302 (18)	0.4963 (9)	0.8265 (3)	0.0548 (13)
N2	0.20830 (17)	0.0240 (8)	0.9488 (3)	0.0437 (11)
N3	0.29606 (17)	0.0913 (8)	0.9509 (3)	0.0473 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.059 (4)	0.094 (5)	0.060 (4)	0.032 (4)	0.014 (3)	0.007 (4)
C2	0.059 (4)	0.101 (6)	0.054 (4)	0.031 (4)	0.020 (3)	0.012 (4)
C3	0.036 (3)	0.051 (4)	0.047 (3)	−0.001 (3)	0.006 (3)	−0.001 (3)
C4	0.055 (4)	0.060 (4)	0.056 (4)	0.016 (3)	0.006 (3)	−0.011 (3)
C5	0.061 (4)	0.063 (4)	0.047 (4)	0.008 (3)	0.003 (3)	−0.007 (3)
C6	0.042 (3)	0.050 (4)	0.052 (3)	−0.004 (3)	0.007 (3)	0.002 (3)
C7	0.044 (3)	0.043 (3)	0.040 (3)	0.006 (3)	0.001 (3)	0.004 (2)
C8	0.053 (4)	0.041 (3)	0.044 (3)	0.009 (3)	−0.001 (3)	0.002 (3)
C9	0.051 (4)	0.048 (4)	0.039 (3)	0.011 (3)	0.001 (3)	0.004 (3)
C10	0.058 (4)	0.058 (4)	0.056 (4)	0.018 (3)	0.011 (3)	0.006 (3)
C11	0.091 (5)	0.054 (4)	0.048 (4)	0.017 (4)	0.017 (4)	−0.003 (3)
C12	0.089 (6)	0.055 (4)	0.065 (4)	0.002 (4)	0.011 (4)	−0.010 (4)
C13	0.065 (4)	0.049 (4)	0.067 (4)	0.001 (3)	0.003 (4)	−0.003 (3)
Hg1	0.0463 (2)	0.0654 (3)	0.0506 (2)	0.000	0.00860 (14)	0.000
I1	0.1231 (5)	0.1306 (6)	0.0804 (4)	0.0764 (4)	0.0547 (3)	0.0385 (4)
N1	0.042 (3)	0.072 (4)	0.048 (3)	0.009 (3)	0.000 (2)	−0.001 (3)
N2	0.036 (3)	0.047 (3)	0.048 (3)	0.002 (2)	0.005 (2)	−0.004 (2)
N3	0.038 (3)	0.049 (3)	0.054 (3)	0.008 (2)	0.004 (2)	0.002 (2)

Geometric parameters (Å, º)

C1—N1	1.317 (7)	C8—N2	1.380 (7)
C1—C2	1.373 (8)	C8—C13	1.389 (8)
C1—H1	0.9300	C8—C9	1.392 (8)
C2—C3	1.372 (8)	C9—N3	1.384 (7)
C2—H2	0.9300	C9—C10	1.404 (8)
C3—C4	1.365 (8)	C10—C11	1.374 (9)
C3—C6	1.523 (7)	C10—H10	0.9300
C4—C5	1.371 (8)	C11—C12	1.385 (9)
C4—H4	0.9300	C11—H11	0.9300
C5—N1	1.315 (7)	C12—C13	1.370 (8)
C5—H5	0.9300	C12—H12	0.9300
C6—N2	1.459 (6)	C13—H13	0.9300
C6—H6A	0.9700	Hg1—N1^ii	2.416 (5)
C6—H6B	0.9700	Hg1—N1	2.416 (5)
C7—N3	1.321 (7)	Hg1—I1^ii	2.6349 (8)
C7—N2	1.384 (7)	Hg1—I1	2.6349 (8)
C7—C7^i	1.447 (11)
N1—C1—C2	123.6 (6)	N3—C9—C10	129.2 (6)
N1—C1—H1	118.2	C8—C9—C10	120.5 (6)
C2—C1—H1	118.2	C11—C10—C9	116.9 (6)
C3—C2—C1	119.2 (6)	C11—C10—H10	121.6
C3—C2—H2	120.4	C9—C10—H10	121.6
C1—C2—H2	120.4	C10—C11—C12	121.9 (6)
C4—C3—C2	117.3 (5)	C10—C11—H11	119.1
C4—C3—C6	122.7 (5)	C12—C11—H11	119.1
C2—C3—C6	120.0 (5)	C13—C12—C11	122.1 (6)
C3—C4—C5	119.3 (6)	C13—C12—H12	119.0
C3—C4—H4	120.3	C11—C12—H12	119.0
C5—C4—H4	120.3	C12—C13—C8	116.8 (6)
N1—C5—C4	123.8 (6)	C12—C13—H13	121.6
N1—C5—H5	118.1	C8—C13—H13	121.6
C4—C5—H5	118.1	N1^ii—Hg1—N1	93.4 (2)
N2—C6—C3	113.8 (5)	N1^ii—Hg1—I1^ii	98.24 (12)
N2—C6—H6A	108.8	N1—Hg1—I1^ii	106.80 (12)
C3—C6—H6A	108.8	N1^ii—Hg1—I1	106.80 (12)
N2—C6—H6B	108.8	N1—Hg1—I1	98.24 (12)
C3—C6—H6B	108.8	I1^ii—Hg1—I1	143.27 (4)
H6A—C6—H6B	107.7	C5—N1—C1	116.7 (5)
N3—C7—N2	113.0 (5)	C5—N1—Hg1	121.6 (4)
N3—C7—C7^i	124.2 (7)	C1—N1—Hg1	121.5 (4)
N2—C7—C7^i	122.8 (6)	C8—N2—C7	105.8 (4)
N2—C8—C13	132.1 (6)	C8—N2—C6	125.1 (5)
N2—C8—C9	106.1 (5)	C7—N2—C6	129.1 (5)
C13—C8—C9	121.8 (6)	C7—N3—C9	104.8 (5)
N3—C9—C8	110.3 (5)
N1—C1—C2—C3	−1.6 (12)	C2—C1—N1—Hg1	−175.5 (6)
C1—C2—C3—C4	1.8 (10)	N1^ii—Hg1—N1—C5	64.5 (5)
C1—C2—C3—C6	−178.9 (6)	I1^ii—Hg1—N1—C5	−35.2 (5)
C2—C3—C4—C5	−0.8 (10)	I1—Hg1—N1—C5	172.0 (5)
C6—C3—C4—C5	−180.0 (6)	N1^ii—Hg1—N1—C1	−120.2 (6)
C3—C4—C5—N1	−0.7 (10)	I1^ii—Hg1—N1—C1	140.2 (5)
C4—C3—C6—N2	45.1 (8)	I1—Hg1—N1—C1	−12.6 (5)
C2—C3—C6—N2	−134.1 (6)	C13—C8—N2—C7	−179.3 (6)
N2—C8—C9—N3	−0.5 (6)	C9—C8—N2—C7	0.7 (6)
C13—C8—C9—N3	179.5 (5)	C13—C8—N2—C6	3.0 (9)
N2—C8—C9—C10	179.0 (5)	C9—C8—N2—C6	−177.1 (5)
C13—C8—C9—C10	−1.0 (9)	N3—C7—N2—C8	−0.7 (6)
N3—C9—C10—C11	178.9 (6)	C7^i—C7—N2—C8	−179.8 (6)
C8—C9—C10—C11	−0.5 (8)	N3—C7—N2—C6	176.9 (5)
C9—C10—C11—C12	1.4 (9)	C7^i—C7—N2—C6	−2.2 (10)
C10—C11—C12—C13	−0.8 (10)	C3—C6—N2—C8	−97.9 (6)
C11—C12—C13—C8	−0.7 (10)	C3—C6—N2—C7	84.8 (7)
N2—C8—C13—C12	−178.4 (6)	N2—C7—N3—C9	0.5 (6)
C9—C8—C13—C12	1.6 (9)	C7^i—C7—N3—C9	179.5 (6)
C4—C5—N1—C1	1.0 (10)	C8—C9—N3—C7	0.0 (6)
C4—C5—N1—Hg1	176.6 (5)	C10—C9—N3—C7	−179.4 (5)
C2—C1—N1—C5	0.1 (11)

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