Coordination-directed one-dimensional coordination polymers generated from a new oxadiazole bridging ligand and HgX₂ (X = Cl, Br and I)

A new 1,3,4-oxadiazole bridging bent organic ligand, 2,5-bis­{5-methyl-2-[(4-pyridyl)meth­oxy]phenyl}-1,3,4-oxadiazole, C₂₈H₂₄N₄O₃, L, has been used to create three novel one-dimensional isomorphic coordination polymers, viz. catena-poly[[[dichloridomercury(II)]-[mu]-2,5-bis­{5-methyl-2-[(4-pyridyl)meth­oxy]phenyl}-1,3,4-oxadiazole] methanol monosolvate], {[HgCl₂(C₂₈H₂₄N₄O₃)]·CH₃OH}_n, catena-poly[[[dibromido­mer­cury(II)]-[mu]-2,5-bis­{5-methyl-2-[(4-pyridyl)methoxy]phenyl}-1,3,4-oxadiazole] methanol monosolvate], {[HgBr₂(C₂₈H₂₄N₄O₃)]·CH₃OH}_n, and catena-poly[[[diiodidomercury(II)]-[mu]-2,5-bis­{5-methyl-2-[(4-pyridyl)methoxy]phenyl}-1,3,4-oxadiazole] methanol monosolvate], {[HgI₂(C₂₈H₂₄N₄O₃)]·CH₃OH}_n. The free L ligand itself adopts a cis conformation, with the two terminal pyridine rings and the central oxadiazole ring almost coplanar [dihedral angles = 5.994 (7) and 9.560 (6)°]. In the Hg^II complexes, however, one of the flexible pyridyl­methyl arms of ligand L is markedly bent and helical chains are obtained. The Hg^II atom lies in a distorted tetra­hedral geometry defined by two pyridine N-atom donors from two L ligands and two halide ligands. The helical chains stack together via inter­chain [pi]-[pi] inter­actions that expand the dimensionality of the structure from one to two. The methanol solvent mol­ecules link to the complex polymers through O-H...N and O-H...O hydrogen bonds.

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) 2,5-bis{5-methyl-2-[(4-pyridyl)methoxy]phenyl}-1,3,4-oxadiazole

Crystal data

C28H24N4O3	F(000) = 976
Mr = 464.51	Dx = 1.302 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 2175 reflections
a = 12.479 (4) Å	θ = 2.2–22.3°
b = 11.452 (4) Å	µ = 0.09 mm^−1
c = 16.776 (6) Å	T = 298 K
β = 98.766 (6)°	Block, colourless
V = 2369.4 (14) Å^3	0.30 × 0.22 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.5°, θmin = 1.9°
φ and ω scans	h = −15→15
12163 measured reflections	k = −13→13
4420 independent reflections	l = −15→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.069P)^2 + 0.0818P] where P = (Fo^2 + 2Fc^2)/3
4420 reflections	(Δ/σ)max = 0.001
318 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 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 intoaccount 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	−0.3160 (2)	0.9444 (2)	0.28664 (16)	0.0826 (8)
H1	−0.3704	0.9862	0.3061	0.099*
C2	−0.30154 (19)	0.9626 (2)	0.20766 (14)	0.0701 (7)
H2	−0.3450	1.0157	0.1756	0.084*
C3	−0.22251 (17)	0.90163 (18)	0.17674 (13)	0.0545 (5)
C4	−0.1615 (2)	0.8250 (2)	0.22736 (13)	0.0686 (7)
H4	−0.1070	0.7815	0.2094	0.082*
C5	−0.1822 (2)	0.8133 (2)	0.30522 (15)	0.0821 (8)
H5	−0.1400	0.7605	0.3385	0.099*
C6	−0.20440 (18)	0.92246 (19)	0.09206 (12)	0.0613 (6)
H6A	−0.2714	0.9106	0.0553	0.074*
H6B	−0.1804	1.0021	0.0861	0.074*
C7	−0.09109 (17)	0.84932 (18)	0.00127 (12)	0.0518 (5)
C8	−0.12648 (19)	0.93317 (19)	−0.05595 (13)	0.0662 (6)
H8	−0.1762	0.9894	−0.0454	0.079*
C9	−0.0877 (2)	0.9333 (2)	−0.12897 (13)	0.0683 (7)
H9	−0.1126	0.9900	−0.1671	0.082*
C10	−0.01387 (18)	0.8525 (2)	−0.14688 (12)	0.0586 (6)
C11	0.02082 (16)	0.76905 (18)	−0.08905 (12)	0.0530 (5)
H11	0.0707	0.7133	−0.1001	0.064*
C12	−0.01635 (15)	0.76563 (16)	−0.01498 (11)	0.0467 (5)
C13	0.0280 (2)	0.8536 (2)	−0.22700 (13)	0.0774 (7)
H13A	0.1057	0.8583	−0.2177	0.116*
H13B	−0.0012	0.9200	−0.2580	0.116*
H13C	0.0059	0.7833	−0.2561	0.116*
C14	0.02523 (15)	0.67632 (16)	0.04350 (12)	0.0453 (5)
C15	0.12522 (15)	0.53008 (16)	0.08591 (11)	0.0442 (5)
C16	0.20873 (15)	0.44270 (16)	0.07948 (12)	0.0467 (5)
C17	0.25498 (17)	0.43820 (17)	0.00910 (13)	0.0566 (6)
H17	0.2293	0.4885	−0.0330	0.068*
C18	0.33780 (19)	0.3617 (2)	−0.00037 (14)	0.0643 (6)
C19	0.3735 (2)	0.2886 (2)	0.06317 (15)	0.0715 (7)
H19	0.4294	0.2367	0.0584	0.086*
C20	0.32960 (19)	0.2895 (2)	0.13363 (14)	0.0670 (6)
H20	0.3549	0.2378	0.1750	0.080*
C21	0.24763 (17)	0.36757 (17)	0.14278 (12)	0.0526 (5)
C22	0.3868 (2)	0.3605 (3)	−0.07722 (16)	0.0979 (9)
H22A	0.4442	0.4169	−0.0735	0.147*
H22B	0.3321	0.3795	−0.1220	0.147*
H22C	0.4154	0.2842	−0.0851	0.147*
C23	0.23533 (17)	0.29890 (18)	0.27457 (12)	0.0581 (6)
H23A	0.3135	0.3030	0.2894	0.070*
H23B	0.2161	0.2196	0.2578	0.070*
C24	0.18154 (16)	0.33104 (17)	0.34535 (12)	0.0498 (5)
C25	0.1988 (2)	0.2626 (2)	0.41242 (14)	0.0753 (7)
H25	0.2401	0.1950	0.4122	0.090*
C26	0.1563 (2)	0.2920 (3)	0.47990 (15)	0.0827 (8)
H26	0.1714	0.2438	0.5248	0.099*
C27	0.07663 (19)	0.4495 (2)	0.41858 (15)	0.0678 (6)
H27	0.0324	0.5147	0.4195	0.081*
C28	0.11751 (17)	0.42766 (18)	0.34910 (13)	0.0571 (6)
H28	0.1022	0.4774	0.3050	0.069*
N1	0.08002 (14)	0.56504 (14)	0.14578 (10)	0.0580 (5)
N2	0.01484 (14)	0.66075 (15)	0.11814 (10)	0.0597 (5)
N3	−0.2575 (2)	0.8714 (2)	0.33620 (13)	0.0840 (6)
N4	0.09524 (16)	0.38440 (19)	0.48528 (12)	0.0731 (6)
O1	0.09262 (10)	0.59513 (11)	0.01848 (7)	0.0469 (3)
O2	−0.12424 (12)	0.84302 (13)	0.07424 (8)	0.0635 (4)
O3	0.20095 (12)	0.37715 (13)	0.21061 (8)	0.0644 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0843 (19)	0.093 (2)	0.0783 (19)	0.0130 (16)	0.0363 (15)	−0.0085 (16)
C2	0.0675 (16)	0.0768 (16)	0.0679 (16)	0.0147 (13)	0.0169 (12)	−0.0010 (13)
C3	0.0570 (13)	0.0580 (13)	0.0497 (13)	0.0019 (11)	0.0115 (10)	0.0005 (11)
C4	0.0791 (17)	0.0769 (16)	0.0524 (14)	0.0217 (13)	0.0188 (12)	0.0084 (13)
C5	0.105 (2)	0.0886 (18)	0.0560 (16)	0.0251 (16)	0.0235 (14)	0.0105 (14)
C6	0.0651 (14)	0.0659 (14)	0.0542 (14)	0.0192 (12)	0.0127 (11)	0.0066 (11)
C7	0.0574 (13)	0.0590 (12)	0.0394 (12)	0.0032 (10)	0.0085 (9)	0.0075 (10)
C8	0.0744 (16)	0.0708 (15)	0.0542 (14)	0.0163 (12)	0.0125 (12)	0.0120 (12)
C9	0.0838 (17)	0.0695 (15)	0.0516 (14)	0.0068 (13)	0.0109 (12)	0.0207 (12)
C10	0.0667 (15)	0.0683 (14)	0.0419 (12)	−0.0091 (12)	0.0118 (10)	0.0091 (11)
C11	0.0544 (13)	0.0600 (13)	0.0460 (12)	−0.0032 (10)	0.0125 (10)	0.0043 (11)
C12	0.0492 (12)	0.0521 (11)	0.0392 (11)	−0.0034 (10)	0.0075 (9)	0.0035 (10)
C13	0.0887 (18)	0.0934 (18)	0.0531 (15)	−0.0100 (15)	0.0198 (13)	0.0128 (13)
C14	0.0453 (11)	0.0496 (11)	0.0431 (12)	−0.0006 (9)	0.0130 (9)	−0.0015 (10)
C15	0.0469 (11)	0.0453 (10)	0.0416 (11)	−0.0042 (9)	0.0108 (9)	0.0043 (9)
C16	0.0497 (12)	0.0431 (10)	0.0491 (12)	−0.0045 (9)	0.0135 (9)	−0.0024 (9)
C17	0.0679 (14)	0.0529 (12)	0.0518 (13)	0.0007 (11)	0.0180 (11)	0.0011 (10)
C18	0.0743 (16)	0.0625 (14)	0.0621 (15)	0.0096 (12)	0.0299 (12)	−0.0020 (12)
C19	0.0789 (17)	0.0676 (15)	0.0743 (17)	0.0213 (13)	0.0320 (14)	0.0013 (13)
C20	0.0759 (16)	0.0646 (14)	0.0640 (15)	0.0199 (12)	0.0217 (12)	0.0095 (12)
C21	0.0577 (13)	0.0528 (12)	0.0501 (13)	0.0054 (10)	0.0179 (10)	−0.0004 (10)
C22	0.120 (2)	0.107 (2)	0.0793 (19)	0.0331 (18)	0.0557 (17)	0.0084 (16)
C23	0.0622 (14)	0.0557 (12)	0.0579 (14)	0.0120 (11)	0.0136 (11)	0.0074 (11)
C24	0.0475 (12)	0.0515 (12)	0.0501 (13)	0.0010 (10)	0.0062 (9)	0.0010 (10)
C25	0.0842 (18)	0.0834 (17)	0.0609 (16)	0.0345 (14)	0.0194 (13)	0.0227 (14)
C26	0.092 (2)	0.102 (2)	0.0571 (16)	0.0235 (16)	0.0209 (14)	0.0216 (15)
C27	0.0714 (16)	0.0603 (14)	0.0740 (17)	0.0076 (12)	0.0187 (13)	−0.0071 (13)
C28	0.0663 (14)	0.0504 (12)	0.0554 (14)	0.0072 (11)	0.0115 (11)	0.0047 (11)
N1	0.0671 (12)	0.0599 (11)	0.0507 (11)	0.0181 (9)	0.0208 (9)	0.0126 (9)
N2	0.0675 (12)	0.0649 (11)	0.0502 (11)	0.0211 (9)	0.0200 (9)	0.0147 (9)
N3	0.1013 (17)	0.0946 (16)	0.0621 (14)	0.0101 (14)	0.0320 (13)	0.0005 (13)
N4	0.0758 (14)	0.0852 (14)	0.0617 (13)	0.0023 (12)	0.0209 (10)	−0.0071 (12)
O1	0.0517 (8)	0.0484 (7)	0.0417 (8)	−0.0012 (6)	0.0105 (6)	0.0011 (6)
O2	0.0758 (10)	0.0721 (10)	0.0461 (9)	0.0274 (8)	0.0205 (8)	0.0134 (7)
O3	0.0786 (10)	0.0680 (9)	0.0507 (9)	0.0267 (8)	0.0233 (8)	0.0155 (7)

Geometric parameters (Å, º)

C1—N3	1.319 (3)	C15—O1	1.364 (2)
C1—C2	1.380 (3)	C15—C16	1.461 (3)
C1—H1	0.9300	C16—C17	1.392 (3)
C2—C3	1.373 (3)	C16—C21	1.395 (3)
C2—H2	0.9300	C17—C18	1.383 (3)
C3—C4	1.369 (3)	C17—H17	0.9300
C3—C6	1.491 (3)	C18—C19	1.374 (3)
C4—C5	1.376 (3)	C18—C22	1.509 (3)
C4—H4	0.9300	C19—C20	1.376 (3)
C5—N3	1.320 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.384 (3)
C6—O2	1.417 (2)	C20—H20	0.9300
C6—H6A	0.9700	C21—O3	1.360 (2)
C6—H6B	0.9700	C22—H22A	0.9600
C7—O2	1.353 (2)	C22—H22B	0.9600
C7—C8	1.382 (3)	C22—H22C	0.9600
C7—C12	1.393 (3)	C23—O3	1.413 (2)
C8—C9	1.384 (3)	C23—C24	1.496 (3)
C8—H8	0.9300	C23—H23A	0.9700
C9—C10	1.371 (3)	C23—H23B	0.9700
C9—H9	0.9300	C24—C25	1.361 (3)
C10—C11	1.384 (3)	C24—C28	1.372 (3)
C10—C13	1.514 (3)	C25—C26	1.364 (3)
C11—C12	1.392 (3)	C25—H25	0.9300
C11—H11	0.9300	C26—N4	1.315 (3)
C12—C14	1.457 (3)	C26—H26	0.9300
C13—H13A	0.9600	C27—N4	1.335 (3)
C13—H13B	0.9600	C27—C28	1.365 (3)
C13—H13C	0.9600	C27—H27	0.9300
C14—N2	1.291 (2)	C28—H28	0.9300
C14—O1	1.362 (2)	N1—N2	1.401 (2)
C15—N1	1.288 (2)
N3—C1—C2	124.0 (2)	C17—C16—C15	118.74 (18)
N3—C1—H1	118.0	C21—C16—C15	122.38 (17)
C2—C1—H1	118.0	C18—C17—C16	122.3 (2)
C3—C2—C1	119.5 (2)	C18—C17—H17	118.8
C3—C2—H2	120.2	C16—C17—H17	118.8
C1—C2—H2	120.2	C19—C18—C17	117.1 (2)
C4—C3—C2	117.1 (2)	C19—C18—C22	122.1 (2)
C4—C3—C6	122.87 (19)	C17—C18—C22	120.8 (2)
C2—C3—C6	120.0 (2)	C18—C19—C20	122.5 (2)
C3—C4—C5	119.0 (2)	C18—C19—H19	118.8
C3—C4—H4	120.5	C20—C19—H19	118.8
C5—C4—H4	120.5	C19—C20—C21	119.8 (2)
N3—C5—C4	124.9 (2)	C19—C20—H20	120.1
N3—C5—H5	117.5	C21—C20—H20	120.1
C4—C5—H5	117.5	O3—C21—C20	124.3 (2)
O2—C6—C3	108.21 (16)	O3—C21—C16	116.33 (17)
O2—C6—H6A	110.1	C20—C21—C16	119.40 (19)
C3—C6—H6A	110.1	C18—C22—H22A	109.5
O2—C6—H6B	110.1	C18—C22—H22B	109.5
C3—C6—H6B	110.1	H22A—C22—H22B	109.5
H6A—C6—H6B	108.4	C18—C22—H22C	109.5
O2—C7—C8	123.81 (19)	H22A—C22—H22C	109.5
O2—C7—C12	116.53 (17)	H22B—C22—H22C	109.5
C8—C7—C12	119.66 (19)	O3—C23—C24	108.99 (16)
C7—C8—C9	119.9 (2)	O3—C23—H23A	109.9
C7—C8—H8	120.1	C24—C23—H23A	109.9
C9—C8—H8	120.1	O3—C23—H23B	109.9
C10—C9—C8	122.0 (2)	C24—C23—H23B	109.9
C10—C9—H9	119.0	H23A—C23—H23B	108.3
C8—C9—H9	119.0	C25—C24—C28	116.5 (2)
C9—C10—C11	117.48 (19)	C25—C24—C23	118.72 (19)
C9—C10—C13	121.5 (2)	C28—C24—C23	124.72 (19)
C11—C10—C13	121.0 (2)	C24—C25—C26	120.7 (2)
C10—C11—C12	122.3 (2)	C24—C25—H25	119.6
C10—C11—H11	118.9	C26—C25—H25	119.6
C12—C11—H11	118.9	N4—C26—C25	124.0 (2)
C11—C12—C7	118.65 (18)	N4—C26—H26	118.0
C11—C12—C14	119.21 (18)	C25—C26—H26	118.0
C7—C12—C14	122.12 (17)	N4—C27—C28	125.0 (2)
C10—C13—H13A	109.5	N4—C27—H27	117.5
C10—C13—H13B	109.5	C28—C27—H27	117.5
H13A—C13—H13B	109.5	C27—C28—C24	118.9 (2)
C10—C13—H13C	109.5	C27—C28—H28	120.6
H13A—C13—H13C	109.5	C24—C28—H28	120.6
H13B—C13—H13C	109.5	C15—N1—N2	106.64 (15)
N2—C14—O1	111.26 (17)	C14—N2—N1	106.85 (15)
N2—C14—C12	132.22 (17)	C1—N3—C5	115.5 (2)
O1—C14—C12	116.43 (16)	C26—N4—C27	114.8 (2)
N1—C15—O1	111.48 (16)	C14—O1—C15	103.74 (14)
N1—C15—C16	132.27 (18)	C7—O2—C6	118.66 (15)
O1—C15—C16	116.04 (16)	C21—O3—C23	117.71 (15)
C17—C16—C21	118.79 (18)
N3—C1—C2—C3	0.5 (4)	C18—C19—C20—C21	−1.2 (4)
C1—C2—C3—C4	−0.1 (3)	C19—C20—C21—O3	−178.4 (2)
C1—C2—C3—C6	−178.6 (2)	C19—C20—C21—C16	1.5 (3)
C2—C3—C4—C5	0.0 (4)	C17—C16—C21—O3	178.82 (18)
C6—C3—C4—C5	178.5 (2)	C15—C16—C21—O3	2.1 (3)
C3—C4—C5—N3	−0.3 (4)	C17—C16—C21—C20	−1.0 (3)
C4—C3—C6—O2	5.6 (3)	C15—C16—C21—C20	−177.7 (2)
C2—C3—C6—O2	−176.0 (2)	O3—C23—C24—C25	176.45 (19)
O2—C7—C8—C9	179.7 (2)	O3—C23—C24—C28	−5.6 (3)
C12—C7—C8—C9	0.2 (3)	C28—C24—C25—C26	−1.7 (3)
C7—C8—C9—C10	−0.4 (4)	C23—C24—C25—C26	176.4 (2)
C8—C9—C10—C11	0.4 (3)	C24—C25—C26—N4	1.4 (4)
C8—C9—C10—C13	−180.0 (2)	N4—C27—C28—C24	1.1 (4)
C9—C10—C11—C12	−0.2 (3)	C25—C24—C28—C27	0.6 (3)
C13—C10—C11—C12	−179.84 (19)	C23—C24—C28—C27	−177.4 (2)
C10—C11—C12—C7	0.0 (3)	O1—C15—N1—N2	−1.3 (2)
C10—C11—C12—C14	−178.96 (18)	C16—C15—N1—N2	173.02 (19)
O2—C7—C12—C11	−179.52 (17)	O1—C14—N2—N1	1.0 (2)
C8—C7—C12—C11	0.0 (3)	C12—C14—N2—N1	−175.38 (19)
O2—C7—C12—C14	−0.6 (3)	C15—N1—N2—C14	0.2 (2)
C8—C7—C12—C14	178.96 (19)	C2—C1—N3—C5	−0.8 (4)
C11—C12—C14—N2	171.1 (2)	C4—C5—N3—C1	0.6 (4)
C7—C12—C14—N2	−7.8 (3)	C25—C26—N4—C27	0.2 (4)
C11—C12—C14—O1	−5.1 (3)	C28—C27—N4—C26	−1.4 (4)
C7—C12—C14—O1	175.98 (17)	N2—C14—O1—C15	−1.7 (2)
N1—C15—C16—C17	−168.9 (2)	C12—C14—O1—C15	175.28 (15)
O1—C15—C16—C17	5.2 (3)	N1—C15—O1—C14	1.9 (2)
N1—C15—C16—C21	7.8 (3)	C16—C15—O1—C14	−173.48 (15)
O1—C15—C16—C21	−178.09 (17)	C8—C7—O2—C6	3.7 (3)
C21—C16—C17—C18	0.2 (3)	C12—C7—O2—C6	−176.79 (18)
C15—C16—C17—C18	177.06 (19)	C3—C6—O2—C7	−177.19 (17)
C16—C17—C18—C19	0.1 (3)	C20—C21—O3—C23	−2.8 (3)
C16—C17—C18—C22	−179.2 (2)	C16—C21—O3—C23	177.37 (17)
C17—C18—C19—C20	0.4 (4)	C24—C23—O3—C21	175.04 (17)
C22—C18—C19—C20	179.7 (2)

(II) catena-poly[[[dichloridomercury(II)]-µ-2,5-bis{5-methyl- 2-[(4-pyridyl)methoxy]phenyl}-1,3,4-oxadiazole] methanol monosolvate]

Crystal data

[Hg2Cl2(C28H24N4O3)]·CH4O	Z = 2
Mr = 768.04	F(000) = 752
Triclinic, P1	Dx = 1.759 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8422 (18) Å	Cell parameters from 3677 reflections
b = 12.927 (3) Å	θ = 2.4–24.5°
c = 13.066 (3) Å	µ = 5.53 mm^−1
α = 95.232 (3)°	T = 298 K
β = 97.758 (3)°	Block, colourless
γ = 99.318 (3)°	0.16 × 0.14 × 0.08 mm
V = 1450.5 (5) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5294 independent reflections
Radiation source: fine-focus sealed tube	4319 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
Tmin = 0.472, Tmax = 0.666	k = −9→15
7519 measured reflections	l = −15→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0724P)^2] where P = (Fo^2 + 2Fc^2)/3
5294 reflections	(Δ/σ)max = 0.002
363 parameters	Δρmax = 1.71 e Å^−3
0 restraints	Δρmin = −2.51 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
Cl1	0.6190 (3)	0.48310 (19)	1.27556 (18)	0.0765 (6)
Cl2	0.2212 (3)	0.3264 (2)	1.4246 (2)	0.0840 (7)
C1	0.8050 (9)	0.3897 (6)	0.5070 (6)	0.0550 (19)
H1	0.8302	0.4151	0.4460	0.066*
C2	0.9242 (9)	0.3840 (6)	0.5850 (6)	0.0514 (17)
H2	1.0269	0.4051	0.5764	0.062*
C3	0.8890 (8)	0.3467 (5)	0.6758 (5)	0.0401 (15)
C4	0.7354 (9)	0.3175 (6)	0.6840 (6)	0.0509 (18)
H4	0.7072	0.2919	0.7442	0.061*
C5	0.6227 (9)	0.3262 (6)	0.6028 (6)	0.0552 (19)
H5	0.5191	0.3070	0.6103	0.066*
C6	1.0139 (8)	0.3402 (5)	0.7644 (5)	0.0463 (16)
H6A	1.1147	0.3619	0.7439	0.056*
H6B	1.0050	0.3884	0.8238	0.056*
C7	1.0527 (7)	0.1606 (5)	0.7323 (5)	0.0394 (14)
C8	1.1368 (8)	0.1814 (6)	0.6529 (5)	0.0506 (17)
H8	1.1638	0.2507	0.6387	0.061*
C9	1.1815 (8)	0.1002 (7)	0.5940 (6)	0.0561 (19)
H9	1.2381	0.1157	0.5406	0.067*
C10	1.1435 (8)	−0.0032 (6)	0.6132 (5)	0.0500 (18)
C11	1.0616 (7)	−0.0231 (5)	0.6934 (5)	0.0432 (15)
H11	1.0362	−0.0924	0.7079	0.052*
C12	1.0149 (7)	0.0571 (5)	0.7543 (5)	0.0382 (14)
C13	1.1914 (10)	−0.0912 (8)	0.5480 (6)	0.071 (3)
H13A	1.1975	−0.0720	0.4792	0.106*
H13B	1.1162	−0.1545	0.5442	0.106*
H13C	1.2909	−0.1031	0.5790	0.106*
C14	0.9278 (7)	0.0299 (5)	0.8381 (5)	0.0366 (14)
C15	0.8112 (7)	−0.0738 (5)	0.9317 (5)	0.0361 (14)
C16	0.7548 (7)	−0.1765 (4)	0.9635 (5)	0.0354 (14)
C17	0.7914 (8)	−0.2667 (5)	0.9125 (5)	0.0474 (16)
H17	0.8507	−0.2592	0.8592	0.057*
C18	0.7429 (10)	−0.3665 (6)	0.9384 (6)	0.0558 (19)
C19	0.6591 (9)	−0.3760 (5)	1.0198 (6)	0.0521 (18)
H19	0.6293	−0.4423	1.0405	0.063*
C20	0.6187 (9)	−0.2886 (5)	1.0710 (6)	0.0508 (17)
H20	0.5592	−0.2968	1.1241	0.061*
C21	0.6670 (8)	−0.1880 (5)	1.0431 (5)	0.0418 (15)
C22	0.7850 (12)	−0.4623 (6)	0.8817 (7)	0.076 (3)
H22A	0.7820	−0.4535	0.8094	0.114*
H22B	0.7122	−0.5239	0.8891	0.114*
H22C	0.8875	−0.4704	0.9108	0.114*
C23	0.5339 (8)	−0.1077 (5)	1.1671 (5)	0.0463 (16)
H23A	0.5789	−0.1440	1.2222	0.056*
H23B	0.4329	−0.1484	1.1375	0.056*
C24	0.5170 (7)	0.0000 (5)	1.2102 (5)	0.0412 (15)
C25	0.5910 (8)	0.0889 (5)	1.1761 (5)	0.0472 (16)
H25	0.6532	0.0836	1.1245	0.057*
C26	0.5719 (8)	0.1866 (6)	1.2196 (5)	0.0467 (16)
H26	0.6233	0.2467	1.1965	0.056*
C27	0.4098 (8)	0.1113 (6)	1.3247 (5)	0.0486 (17)
H27	0.3455	0.1179	1.3748	0.058*
C28	0.4257 (8)	0.0122 (6)	1.2861 (5)	0.0464 (16)
H28	0.3749	−0.0467	1.3112	0.056*
C29	0.7942 (12)	0.3096 (8)	1.0448 (7)	0.079 (3)
H29A	0.8915	0.3236	1.0906	0.118*
H29B	0.7332	0.2456	1.0591	0.118*
H29C	0.7395	0.3671	1.0554	0.118*
Hg1	0.46076 (3)	0.37308 (2)	1.36711 (2)	0.05369 (14)
N1	0.8781 (6)	0.0882 (4)	0.9074 (4)	0.0395 (12)
N2	0.8021 (6)	0.0210 (4)	0.9694 (4)	0.0413 (12)
N3	0.4828 (6)	0.1989 (5)	1.2933 (4)	0.0456 (13)
N4	0.6559 (7)	0.3609 (5)	0.5146 (4)	0.0479 (14)
O1	0.8918 (5)	−0.0737 (3)	0.8499 (3)	0.0389 (10)
O2	0.6302 (6)	−0.0988 (4)	1.0899 (4)	0.0494 (11)
O3	1.0028 (5)	0.2354 (3)	0.7935 (3)	0.0443 (10)
O4	0.8205 (10)	0.2989 (5)	0.9445 (5)	0.088 (2)
H4A	0.8378	0.2394	0.9294	0.133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0793 (15)	0.0688 (15)	0.0822 (14)	−0.0019 (11)	0.0176 (11)	0.0313 (11)
Cl2	0.0803 (15)	0.0824 (18)	0.1061 (17)	0.0273 (13)	0.0504 (14)	0.0229 (14)
C1	0.066 (5)	0.048 (5)	0.057 (4)	0.012 (4)	0.016 (4)	0.025 (3)
C2	0.051 (4)	0.039 (4)	0.070 (5)	0.007 (3)	0.019 (4)	0.019 (3)
C3	0.051 (4)	0.023 (3)	0.051 (4)	0.012 (3)	0.017 (3)	0.008 (3)
C4	0.054 (4)	0.050 (5)	0.051 (4)	0.004 (3)	0.015 (3)	0.016 (3)
C5	0.049 (4)	0.057 (5)	0.060 (4)	0.004 (4)	0.017 (4)	0.009 (4)
C6	0.051 (4)	0.034 (4)	0.059 (4)	0.011 (3)	0.014 (3)	0.012 (3)
C7	0.037 (3)	0.039 (4)	0.044 (3)	0.015 (3)	0.000 (3)	0.006 (3)
C8	0.051 (4)	0.051 (5)	0.056 (4)	0.019 (3)	0.015 (3)	0.015 (3)
C9	0.045 (4)	0.080 (6)	0.051 (4)	0.026 (4)	0.012 (3)	0.016 (4)
C10	0.045 (4)	0.058 (5)	0.049 (4)	0.024 (3)	−0.002 (3)	0.000 (3)
C11	0.045 (4)	0.033 (4)	0.051 (4)	0.013 (3)	0.001 (3)	0.005 (3)
C12	0.037 (3)	0.037 (4)	0.040 (3)	0.013 (3)	−0.004 (3)	0.005 (3)
C13	0.069 (5)	0.094 (7)	0.055 (4)	0.044 (5)	0.006 (4)	−0.012 (4)
C14	0.037 (3)	0.026 (3)	0.045 (3)	0.010 (3)	−0.003 (3)	0.001 (3)
C15	0.041 (3)	0.025 (3)	0.044 (3)	0.011 (3)	−0.001 (3)	0.008 (3)
C16	0.043 (3)	0.017 (3)	0.045 (3)	0.010 (2)	−0.003 (3)	0.002 (2)
C17	0.057 (4)	0.030 (4)	0.056 (4)	0.018 (3)	−0.001 (3)	0.006 (3)
C18	0.068 (5)	0.031 (4)	0.068 (5)	0.021 (3)	−0.002 (4)	0.003 (3)
C19	0.056 (4)	0.025 (4)	0.073 (5)	0.003 (3)	−0.002 (4)	0.012 (3)
C20	0.053 (4)	0.032 (4)	0.066 (4)	0.004 (3)	0.004 (3)	0.011 (3)
C21	0.044 (4)	0.028 (3)	0.051 (4)	0.010 (3)	−0.006 (3)	0.006 (3)
C22	0.105 (7)	0.032 (4)	0.097 (6)	0.033 (5)	0.017 (6)	0.002 (4)
C23	0.049 (4)	0.040 (4)	0.048 (4)	0.002 (3)	0.007 (3)	0.009 (3)
C24	0.043 (4)	0.038 (4)	0.043 (3)	0.012 (3)	−0.001 (3)	0.007 (3)
C25	0.057 (4)	0.039 (4)	0.049 (4)	0.012 (3)	0.017 (3)	0.004 (3)
C26	0.058 (4)	0.034 (4)	0.052 (4)	0.010 (3)	0.018 (3)	0.009 (3)
C27	0.045 (4)	0.054 (5)	0.049 (4)	0.010 (3)	0.012 (3)	0.006 (3)
C28	0.043 (4)	0.043 (4)	0.051 (4)	0.001 (3)	0.005 (3)	0.009 (3)
C29	0.089 (6)	0.087 (7)	0.075 (6)	0.039 (5)	0.028 (5)	0.018 (5)
Hg1	0.0624 (2)	0.0448 (2)	0.0596 (2)	0.01581 (14)	0.01790 (14)	0.01235 (13)
N1	0.046 (3)	0.027 (3)	0.047 (3)	0.010 (2)	0.006 (2)	0.006 (2)
N2	0.052 (3)	0.026 (3)	0.047 (3)	0.010 (2)	0.006 (2)	0.006 (2)
N3	0.048 (3)	0.045 (4)	0.047 (3)	0.014 (3)	0.011 (3)	0.008 (3)
N4	0.055 (4)	0.035 (3)	0.056 (3)	0.011 (3)	0.011 (3)	0.008 (3)
O1	0.047 (3)	0.026 (2)	0.045 (2)	0.0134 (19)	0.0023 (19)	0.0038 (18)
O2	0.064 (3)	0.028 (3)	0.059 (3)	0.010 (2)	0.019 (2)	0.006 (2)
O3	0.055 (3)	0.032 (3)	0.052 (2)	0.015 (2)	0.014 (2)	0.012 (2)
O4	0.151 (6)	0.059 (4)	0.084 (4)	0.059 (4)	0.059 (4)	0.026 (3)

Geometric parameters (Å, º)

Cl1—Hg1	2.352 (2)	C16—C17	1.395 (9)
Cl2—Hg1	2.348 (2)	C17—C18	1.379 (10)
C1—N4	1.330 (9)	C17—H17	0.9300
C1—C2	1.380 (10)	C18—C19	1.380 (11)
C1—H1	0.9300	C18—C22	1.509 (10)
C2—C3	1.375 (9)	C19—C20	1.381 (10)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.371 (10)	C20—C21	1.399 (9)
C3—C6	1.506 (10)	C20—H20	0.9300
C4—C5	1.379 (11)	C21—O2	1.363 (8)
C4—H4	0.9300	C22—H22A	0.9600
C5—N4	1.327 (9)	C22—H22B	0.9600
C5—H5	0.9300	C22—H22C	0.9600
C6—O3	1.432 (8)	C23—O2	1.406 (8)
C6—H6A	0.9700	C23—C24	1.492 (9)
C6—H6B	0.9700	C23—H23A	0.9700
C7—O3	1.365 (7)	C23—H23B	0.9700
C7—C8	1.376 (9)	C24—C25	1.370 (10)
C7—C12	1.391 (9)	C24—C28	1.374 (9)
C8—C9	1.386 (10)	C25—C26	1.383 (10)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.379 (11)	C26—N3	1.338 (8)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.373 (10)	C27—N3	1.337 (9)
C10—C13	1.509 (10)	C27—C28	1.369 (10)
C11—C12	1.398 (9)	C27—H27	0.9300
C11—H11	0.9300	C28—H28	0.9300
C12—C14	1.459 (9)	C29—O4	1.360 (10)
C13—H13A	0.9600	C29—H29A	0.9600
C13—H13B	0.9600	C29—H29B	0.9600
C13—H13C	0.9600	C29—H29C	0.9600
C14—N1	1.292 (8)	Hg1—N3	2.416 (6)
C14—O1	1.354 (7)	Hg1—N4^i	2.441 (6)
C15—N2	1.297 (8)	N1—N2	1.395 (7)
C15—O1	1.362 (7)	N4—Hg1^ii	2.441 (6)
C15—C16	1.459 (8)	O4—H4A	0.8200
C16—C21	1.383 (9)
N4—C1—C2	123.4 (7)	C18—C19—H19	119.5
N4—C1—H1	118.3	C20—C19—H19	119.5
C2—C1—H1	118.3	C19—C20—C21	120.2 (7)
C3—C2—C1	119.1 (7)	C19—C20—H20	119.9
C3—C2—H2	120.5	C21—C20—H20	119.9
C1—C2—H2	120.5	O2—C21—C16	117.2 (6)
C4—C3—C2	117.6 (6)	O2—C21—C20	123.1 (7)
C4—C3—C6	120.9 (6)	C16—C21—C20	119.7 (6)
C2—C3—C6	121.5 (6)	C18—C22—H22A	109.5
C3—C4—C5	119.9 (7)	C18—C22—H22B	109.5
C3—C4—H4	120.0	H22A—C22—H22B	109.5
C5—C4—H4	120.0	C18—C22—H22C	109.5
N4—C5—C4	122.7 (7)	H22A—C22—H22C	109.5
N4—C5—H5	118.6	H22B—C22—H22C	109.5
C4—C5—H5	118.6	O2—C23—C24	109.1 (5)
O3—C6—C3	111.5 (5)	O2—C23—H23A	109.9
O3—C6—H6A	109.3	C24—C23—H23A	109.9
C3—C6—H6A	109.3	O2—C23—H23B	109.9
O3—C6—H6B	109.3	C24—C23—H23B	109.9
C3—C6—H6B	109.3	H23A—C23—H23B	108.3
H6A—C6—H6B	108.0	C25—C24—C28	118.2 (6)
O3—C7—C8	124.5 (6)	C25—C24—C23	121.6 (6)
O3—C7—C12	116.1 (6)	C28—C24—C23	120.3 (6)
C8—C7—C12	119.4 (6)	C24—C25—C26	118.9 (6)
C7—C8—C9	120.6 (7)	C24—C25—H25	120.5
C7—C8—H8	119.7	C26—C25—H25	120.5
C9—C8—H8	119.7	N3—C26—C25	123.1 (7)
C10—C9—C8	121.1 (7)	N3—C26—H26	118.5
C10—C9—H9	119.4	C25—C26—H26	118.5
C8—C9—H9	119.4	N3—C27—C28	122.7 (6)
C11—C10—C9	117.9 (7)	N3—C27—H27	118.7
C11—C10—C13	121.4 (7)	C28—C27—H27	118.7
C9—C10—C13	120.7 (7)	C27—C28—C24	119.9 (7)
C10—C11—C12	122.3 (7)	C27—C28—H28	120.0
C10—C11—H11	118.8	C24—C28—H28	120.0
C12—C11—H11	118.8	O4—C29—H29A	109.5
C7—C12—C11	118.7 (6)	O4—C29—H29B	109.5
C7—C12—C14	122.1 (6)	H29A—C29—H29B	109.5
C11—C12—C14	119.2 (6)	O4—C29—H29C	109.5
C10—C13—H13A	109.5	H29A—C29—H29C	109.5
C10—C13—H13B	109.5	H29B—C29—H29C	109.5
H13A—C13—H13B	109.5	Cl2—Hg1—Cl1	149.21 (10)
C10—C13—H13C	109.5	Cl2—Hg1—N3	97.36 (15)
H13A—C13—H13C	109.5	Cl1—Hg1—N3	102.37 (15)
H13B—C13—H13C	109.5	Cl2—Hg1—N4^i	105.22 (16)
N1—C14—O1	111.4 (6)	Cl1—Hg1—N4^i	98.30 (16)
N1—C14—C12	131.5 (6)	N3—Hg1—N4^i	89.80 (19)
O1—C14—C12	117.2 (5)	C14—N1—N2	107.5 (5)
N2—C15—O1	112.1 (5)	C14—N1—H4A	137.5
N2—C15—C16	131.3 (6)	N2—N1—H4A	113.1
O1—C15—C16	116.6 (5)	C15—N2—N1	105.6 (5)
C21—C16—C17	118.5 (6)	C27—N3—C26	117.2 (6)
C21—C16—C15	122.5 (6)	C27—N3—Hg1	122.1 (4)
C17—C16—C15	119.0 (6)	C26—N3—Hg1	120.7 (5)
C18—C17—C16	122.4 (7)	C5—N4—C1	117.2 (6)
C18—C17—H17	118.8	C5—N4—Hg1^ii	123.9 (5)
C16—C17—H17	118.8	C1—N4—Hg1^ii	118.9 (5)
C17—C18—C19	118.1 (7)	C14—O1—C15	103.5 (5)
C17—C18—C22	121.0 (8)	C21—O2—C23	119.0 (5)
C19—C18—C22	120.8 (7)	C7—O3—C6	119.0 (5)
C18—C19—C20	121.0 (7)	C29—O4—H4A	109.5
N4—C1—C2—C3	0.1 (11)	C19—C20—C21—C16	0.4 (10)
C1—C2—C3—C4	−0.4 (10)	O2—C23—C24—C25	−1.2 (8)
C1—C2—C3—C6	−179.0 (6)	O2—C23—C24—C28	178.9 (6)
C2—C3—C4—C5	0.0 (11)	C28—C24—C25—C26	0.4 (10)
C6—C3—C4—C5	178.6 (7)	C23—C24—C25—C26	−179.5 (6)
C3—C4—C5—N4	0.9 (12)	C24—C25—C26—N3	−0.6 (11)
C4—C3—C6—O3	57.3 (8)	N3—C27—C28—C24	−1.6 (10)
C2—C3—C6—O3	−124.2 (7)	C25—C24—C28—C27	0.6 (10)
O3—C7—C8—C9	−179.4 (6)	C23—C24—C28—C27	−179.5 (6)
C12—C7—C8—C9	1.1 (10)	O1—C14—N1—N2	−0.8 (6)
C7—C8—C9—C10	−0.1 (11)	C12—C14—N1—N2	−179.6 (6)
C8—C9—C10—C11	−0.8 (10)	O1—C14—N1—H4A	−163.2
C8—C9—C10—C13	179.4 (6)	C12—C14—N1—H4A	18.0
C9—C10—C11—C12	0.8 (10)	O1—C15—N2—N1	1.5 (6)
C13—C10—C11—C12	−179.4 (6)	C16—C15—N2—N1	179.5 (6)
O3—C7—C12—C11	179.4 (5)	C14—N1—N2—C15	−0.4 (6)
C8—C7—C12—C11	−1.1 (9)	H4A—N1—N2—C15	166.8
O3—C7—C12—C14	−0.3 (8)	C28—C27—N3—C26	1.3 (10)
C8—C7—C12—C14	179.2 (6)	C28—C27—N3—Hg1	−177.6 (5)
C10—C11—C12—C7	0.2 (9)	C25—C26—N3—C27	−0.2 (10)
C10—C11—C12—C14	179.9 (6)	C25—C26—N3—Hg1	178.7 (5)
C7—C12—C14—N1	−4.0 (10)	Cl2—Hg1—N3—C27	−24.2 (5)
C11—C12—C14—N1	176.3 (6)	Cl1—Hg1—N3—C27	179.6 (5)
C7—C12—C14—O1	177.3 (5)	N4^i—Hg1—N3—C27	81.1 (5)
C11—C12—C14—O1	−2.4 (8)	Cl2—Hg1—N3—C26	156.9 (5)
N2—C15—C16—C21	4.2 (10)	Cl1—Hg1—N3—C26	0.7 (5)
O1—C15—C16—C21	−177.8 (5)	N4^i—Hg1—N3—C26	−97.8 (5)
N2—C15—C16—C17	−175.3 (6)	C4—C5—N4—C1	−1.2 (11)
O1—C15—C16—C17	2.7 (8)	C4—C5—N4—Hg1^ii	178.3 (6)
C21—C16—C17—C18	0.2 (10)	C2—C1—N4—C5	0.8 (11)
C15—C16—C17—C18	179.8 (6)	C2—C1—N4—Hg1^ii	−178.7 (6)
C16—C17—C18—C19	−2.0 (11)	N1—C14—O1—C15	1.6 (6)
C16—C17—C18—C22	−179.8 (7)	C12—C14—O1—C15	−179.4 (5)
C17—C18—C19—C20	2.9 (11)	N2—C15—O1—C14	−1.9 (6)
C22—C18—C19—C20	−179.2 (7)	C16—C15—O1—C14	179.8 (5)
C18—C19—C20—C21	−2.2 (11)	C16—C21—O2—C23	176.5 (6)
C17—C16—C21—O2	−178.6 (5)	C20—C21—O2—C23	−2.7 (9)
C15—C16—C21—O2	1.9 (9)	C24—C23—O2—C21	177.1 (5)
C17—C16—C21—C20	0.6 (9)	C8—C7—O3—C6	11.1 (9)
C15—C16—C21—C20	−178.9 (6)	C12—C7—O3—C6	−169.4 (5)
C19—C20—C21—O2	179.5 (6)	C3—C6—O3—C7	76.3 (7)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N1	0.82	2.05	2.862 (8)	174
O4—H4A···O3	0.82	2.45	2.856 (7)	112

(III) catena-poly[[[dibromidomercury(II)]-µ-2,5-bis{5-methyl- 2-[(4-pyridyl)methoxy]phenyl}-1,3,4-oxadiazole] methanol monosolvate]

Crystal data

[Hg2Br2(C28H24N4O3)]·CH4O	Z = 2
Mr = 856.96	F(000) = 824
Triclinic, P1	Dx = 1.974 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8247 (12) Å	Cell parameters from 4801 reflections
b = 12.9673 (18) Å	θ = 2.4–28.1°
c = 13.0197 (18) Å	µ = 8.15 mm^−1
α = 95.747 (2)°	T = 123 K
β = 99.101 (2)°	Block, colourless
γ = 98.902 (2)°	0.40 × 0.28 × 0.10 mm
V = 1441.5 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5274 independent reflections
Radiation source: fine-focus sealed tube	4754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
Tmin = 0.139, Tmax = 0.496	k = −15→15
7538 measured reflections	l = −15→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0848P)^2] where P = (Fo^2 + 2Fc^2)/3
5274 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 2.73 e Å^−3
0 restraints	Δρmin = −3.43 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
Br1	0.61390 (9)	0.48874 (6)	1.27101 (5)	0.03088 (19)
Br2	0.19318 (9)	0.32231 (6)	1.41557 (6)	0.03231 (19)
C1	0.7988 (8)	0.3911 (5)	0.5109 (5)	0.0251 (15)
H1	0.8237	0.4191	0.4498	0.030*
C2	0.9202 (8)	0.3855 (5)	0.5910 (5)	0.0236 (14)
H2	1.0254	0.4089	0.5847	0.028*
C3	0.8845 (8)	0.3451 (5)	0.6802 (5)	0.0182 (13)
C4	0.7297 (8)	0.3125 (5)	0.6856 (5)	0.0257 (15)
H4	0.7020	0.2843	0.7460	0.031*
C5	0.6145 (8)	0.3211 (5)	0.6023 (5)	0.0263 (15)
H5	0.5083	0.2993	0.6071	0.032*
C6	1.0121 (8)	0.3385 (5)	0.7714 (5)	0.0217 (14)
H6A	1.1153	0.3602	0.7519	0.026*
H6B	1.0036	0.3875	0.8328	0.026*
C7	1.0503 (7)	0.1601 (5)	0.7363 (5)	0.0187 (13)
C8	1.1326 (8)	0.1814 (5)	0.6571 (5)	0.0214 (13)
H8	1.1594	0.2519	0.6435	0.026*
C9	1.1770 (8)	0.0997 (6)	0.5968 (5)	0.0238 (14)
H9	1.2334	0.1158	0.5424	0.029*
C10	1.1410 (8)	−0.0035 (5)	0.6143 (5)	0.0236 (14)
C11	1.0602 (8)	−0.0249 (5)	0.6948 (5)	0.0222 (14)
H11	1.0353	−0.0956	0.7084	0.027*
C12	1.0141 (7)	0.0555 (5)	0.7568 (5)	0.0174 (13)
C13	1.1906 (9)	−0.0914 (6)	0.5480 (5)	0.0310 (16)
H13A	1.1759	−0.0784	0.4745	0.046*
H13B	1.1272	−0.1589	0.5540	0.046*
H13C	1.3008	−0.0935	0.5728	0.046*
C14	0.9285 (7)	0.0294 (5)	0.8402 (5)	0.0154 (12)
C15	0.8123 (7)	−0.0756 (5)	0.9320 (5)	0.0171 (12)
C16	0.7549 (7)	−0.1783 (5)	0.9633 (5)	0.0168 (13)
C17	0.7998 (8)	−0.2679 (5)	0.9122 (5)	0.0207 (13)
H17	0.8615	−0.2598	0.8591	0.025*
C18	0.7538 (8)	−0.3678 (5)	0.9398 (5)	0.0232 (14)
C19	0.6653 (8)	−0.3766 (5)	1.0173 (5)	0.0245 (15)
H19	0.6350	−0.4443	1.0371	0.029*
C20	0.6183 (8)	−0.2910 (5)	1.0677 (5)	0.0240 (14)
H20	0.5549	−0.3003	1.1198	0.029*
C21	0.6657 (7)	−0.1901 (5)	1.0408 (5)	0.0190 (13)
C22	0.8045 (10)	−0.4619 (5)	0.8859 (6)	0.0332 (17)
H22A	0.8021	−0.4543	0.8115	0.050*
H22B	0.7337	−0.5261	0.8923	0.050*
H22C	0.9108	−0.4664	0.9188	0.050*
C23	0.5319 (7)	−0.1107 (5)	1.1651 (5)	0.0188 (13)
H23A	0.5827	−0.1463	1.2215	0.023*
H23B	0.4281	−0.1532	1.1356	0.023*
C24	0.5150 (7)	−0.0023 (5)	1.2083 (5)	0.0194 (13)
C25	0.5905 (8)	0.0879 (5)	1.1772 (5)	0.0216 (13)
H25	0.6549	0.0832	1.1256	0.026*
C26	0.5710 (8)	0.1842 (5)	1.2219 (5)	0.0236 (14)
H26	0.6238	0.2458	1.2005	0.028*
C27	0.4076 (8)	0.1086 (5)	1.3251 (5)	0.0213 (13)
H27	0.3429	0.1154	1.3763	0.026*
C28	0.4232 (8)	0.0091 (5)	1.2846 (5)	0.0220 (14)
H28	0.3715	−0.0512	1.3088	0.026*
C29	0.7860 (10)	0.3041 (6)	1.0472 (6)	0.0371 (19)
H29A	0.8834	0.3188	1.0983	0.056*
H29B	0.7245	0.2373	1.0571	0.056*
H29C	0.7263	0.3609	1.0576	0.056*
Hg1	0.45331 (3)	0.368829 (18)	1.365854 (17)	0.02196 (12)
N1	0.8778 (6)	0.0868 (4)	0.9089 (4)	0.0182 (11)
N2	0.8016 (6)	0.0181 (4)	0.9699 (4)	0.0185 (11)
N3	0.4796 (6)	0.1952 (4)	1.2951 (4)	0.0191 (11)
N4	0.6492 (6)	0.3594 (4)	0.5151 (4)	0.0215 (11)
O1	0.8910 (5)	−0.0755 (3)	0.8503 (3)	0.0184 (9)
O2	0.6245 (6)	−0.1009 (3)	1.0854 (3)	0.0229 (10)
O3	0.9998 (5)	0.2333 (3)	0.7987 (3)	0.0196 (9)
O4	0.8198 (7)	0.2975 (4)	0.9458 (4)	0.0361 (13)
H4A	0.8495	0.2401	0.9314	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0337 (4)	0.0293 (4)	0.0294 (4)	−0.0007 (3)	0.0060 (3)	0.0117 (3)
Br2	0.0322 (4)	0.0297 (4)	0.0397 (4)	0.0073 (3)	0.0180 (3)	0.0049 (3)
C1	0.031 (4)	0.020 (3)	0.028 (3)	0.009 (3)	0.009 (3)	0.006 (3)
C2	0.028 (4)	0.019 (3)	0.025 (3)	0.000 (3)	0.008 (3)	0.007 (3)
C3	0.028 (4)	0.009 (3)	0.020 (3)	0.007 (2)	0.008 (3)	0.002 (2)
C4	0.028 (4)	0.028 (4)	0.022 (3)	0.005 (3)	0.006 (3)	0.007 (3)
C5	0.024 (4)	0.029 (4)	0.027 (4)	0.006 (3)	0.004 (3)	0.006 (3)
C6	0.027 (4)	0.014 (3)	0.026 (3)	0.005 (3)	0.004 (3)	0.007 (2)
C7	0.017 (3)	0.022 (3)	0.017 (3)	0.008 (3)	−0.001 (2)	0.001 (2)
C8	0.021 (3)	0.019 (3)	0.023 (3)	0.003 (3)	0.001 (3)	0.003 (2)
C9	0.020 (3)	0.037 (4)	0.019 (3)	0.014 (3)	0.006 (3)	0.007 (3)
C10	0.020 (3)	0.028 (4)	0.020 (3)	0.009 (3)	−0.005 (3)	−0.003 (3)
C11	0.026 (4)	0.020 (3)	0.020 (3)	0.011 (3)	−0.003 (3)	0.001 (2)
C12	0.017 (3)	0.019 (3)	0.015 (3)	0.005 (2)	−0.004 (2)	0.003 (2)
C13	0.031 (4)	0.036 (4)	0.027 (4)	0.014 (3)	0.003 (3)	−0.004 (3)
C14	0.014 (3)	0.011 (3)	0.020 (3)	0.003 (2)	−0.002 (2)	0.004 (2)
C15	0.012 (3)	0.019 (3)	0.018 (3)	0.001 (2)	−0.002 (2)	0.000 (2)
C16	0.017 (3)	0.011 (3)	0.020 (3)	0.001 (2)	−0.005 (2)	0.004 (2)
C17	0.026 (4)	0.017 (3)	0.017 (3)	0.008 (3)	−0.005 (3)	0.002 (2)
C18	0.029 (4)	0.017 (3)	0.021 (3)	0.009 (3)	−0.008 (3)	−0.002 (2)
C19	0.029 (4)	0.012 (3)	0.029 (3)	0.002 (3)	−0.004 (3)	0.006 (3)
C20	0.025 (4)	0.020 (3)	0.024 (3)	−0.002 (3)	−0.001 (3)	0.006 (3)
C21	0.017 (3)	0.016 (3)	0.020 (3)	−0.001 (2)	−0.006 (2)	−0.001 (2)
C22	0.051 (5)	0.016 (3)	0.034 (4)	0.014 (3)	0.004 (3)	0.004 (3)
C23	0.020 (3)	0.017 (3)	0.020 (3)	0.002 (2)	0.003 (2)	0.004 (2)
C24	0.020 (3)	0.020 (3)	0.016 (3)	0.005 (3)	−0.005 (2)	0.003 (2)
C25	0.023 (4)	0.022 (3)	0.022 (3)	0.006 (3)	0.007 (3)	0.002 (2)
C26	0.027 (4)	0.017 (3)	0.026 (3)	0.004 (3)	0.004 (3)	0.004 (3)
C27	0.023 (3)	0.022 (3)	0.018 (3)	0.003 (3)	0.000 (2)	0.003 (2)
C28	0.023 (4)	0.021 (3)	0.020 (3)	0.001 (3)	0.001 (3)	0.003 (2)
C29	0.054 (5)	0.037 (4)	0.028 (4)	0.021 (4)	0.015 (4)	0.008 (3)
Hg1	0.02546 (18)	0.01910 (17)	0.02258 (17)	0.00511 (11)	0.00594 (11)	0.00398 (10)
N1	0.023 (3)	0.011 (2)	0.019 (3)	0.003 (2)	0.002 (2)	0.0013 (19)
N2	0.023 (3)	0.013 (3)	0.018 (3)	0.004 (2)	−0.001 (2)	0.0051 (19)
N3	0.021 (3)	0.021 (3)	0.016 (3)	0.009 (2)	0.003 (2)	0.002 (2)
N4	0.022 (3)	0.019 (3)	0.024 (3)	0.003 (2)	0.002 (2)	0.005 (2)
O1	0.026 (3)	0.011 (2)	0.019 (2)	0.0057 (18)	0.0009 (18)	0.0035 (16)
O2	0.033 (3)	0.012 (2)	0.025 (2)	0.0036 (19)	0.0079 (19)	0.0006 (17)
O3	0.024 (2)	0.013 (2)	0.025 (2)	0.0066 (18)	0.0055 (18)	0.0050 (17)
O4	0.062 (4)	0.025 (3)	0.032 (3)	0.021 (3)	0.024 (3)	0.010 (2)

Geometric parameters (Å, º)

Br1—Hg1	2.4914 (7)	C16—C17	1.422 (8)
Br2—Hg1	2.4844 (8)	C17—C18	1.396 (9)
C1—N4	1.332 (9)	C17—H17	0.9500
C1—C2	1.388 (10)	C18—C19	1.374 (10)
C1—H1	0.9500	C18—C22	1.510 (9)
C2—C3	1.381 (9)	C19—C20	1.385 (9)
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.382 (10)	C20—C21	1.406 (9)
C3—C6	1.520 (9)	C20—H20	0.9500
C4—C5	1.390 (10)	C21—O2	1.367 (7)
C4—H4	0.9500	C22—H22A	0.9800
C5—N4	1.343 (9)	C22—H22B	0.9800
C5—H5	0.9500	C22—H22C	0.9800
C6—O3	1.436 (7)	C23—O2	1.423 (7)
C6—H6A	0.9900	C23—C24	1.499 (8)
C6—H6B	0.9900	C23—H23A	0.9900
C7—O3	1.359 (7)	C23—H23B	0.9900
C7—C8	1.378 (9)	C24—C25	1.384 (9)
C7—C12	1.407 (9)	C24—C28	1.388 (9)
C8—C9	1.396 (9)	C25—C26	1.371 (9)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.378 (10)	C26—N3	1.352 (8)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.385 (10)	C27—N3	1.328 (9)
C10—C13	1.521 (9)	C27—C28	1.380 (9)
C11—C12	1.403 (8)	C27—H27	0.9500
C11—H11	0.9500	C28—H28	0.9500
C12—C14	1.456 (9)	C29—O4	1.397 (8)
C13—H13A	0.9800	C29—H29A	0.9800
C13—H13B	0.9800	C29—H29B	0.9800
C13—H13C	0.9800	C29—H29C	0.9800
C14—N1	1.284 (8)	Hg1—N3	2.405 (5)
C14—O1	1.374 (7)	Hg1—N4^i	2.415 (5)
C15—N2	1.288 (8)	N1—N2	1.415 (7)
C15—O1	1.359 (8)	N4—Hg1^ii	2.415 (5)
C15—C16	1.470 (9)	O4—H4A	0.8400
C16—C21	1.381 (9)
N4—C1—C2	123.5 (6)	C18—C19—H19	118.6
N4—C1—H1	118.2	C20—C19—H19	118.6
C2—C1—H1	118.2	C19—C20—C21	119.1 (7)
C3—C2—C1	118.5 (7)	C19—C20—H20	120.4
C3—C2—H2	120.8	C21—C20—H20	120.4
C1—C2—H2	120.8	O2—C21—C16	116.7 (6)
C2—C3—C4	118.4 (6)	O2—C21—C20	123.6 (6)
C2—C3—C6	121.0 (6)	C16—C21—C20	119.7 (6)
C4—C3—C6	120.6 (6)	C18—C22—H22A	109.5
C3—C4—C5	119.8 (6)	C18—C22—H22B	109.5
C3—C4—H4	120.1	H22A—C22—H22B	109.5
C5—C4—H4	120.1	C18—C22—H22C	109.5
N4—C5—C4	121.8 (7)	H22A—C22—H22C	109.5
N4—C5—H5	119.1	H22B—C22—H22C	109.5
C4—C5—H5	119.1	O2—C23—C24	108.0 (5)
O3—C6—C3	110.8 (5)	O2—C23—H23A	110.1
O3—C6—H6A	109.5	C24—C23—H23A	110.1
C3—C6—H6A	109.5	O2—C23—H23B	110.1
O3—C6—H6B	109.5	C24—C23—H23B	110.1
C3—C6—H6B	109.5	H23A—C23—H23B	108.4
H6A—C6—H6B	108.1	C25—C24—C28	118.1 (6)
O3—C7—C8	125.1 (6)	C25—C24—C23	122.8 (6)
O3—C7—C12	115.8 (6)	C28—C24—C23	119.1 (6)
C8—C7—C12	119.1 (6)	C26—C25—C24	119.1 (6)
C7—C8—C9	120.3 (6)	C26—C25—H25	120.4
C7—C8—H8	119.8	C24—C25—H25	120.4
C9—C8—H8	119.8	N3—C26—C25	122.7 (6)
C10—C9—C8	121.7 (6)	N3—C26—H26	118.6
C10—C9—H9	119.2	C25—C26—H26	118.6
C8—C9—H9	119.2	N3—C27—C28	122.4 (6)
C9—C10—C11	118.2 (6)	N3—C27—H27	118.8
C9—C10—C13	120.9 (6)	C28—C27—H27	118.8
C11—C10—C13	120.9 (6)	C27—C28—C24	119.5 (6)
C10—C11—C12	121.5 (6)	C27—C28—H28	120.2
C10—C11—H11	119.3	C24—C28—H28	120.2
C12—C11—H11	119.3	O4—C29—H29A	109.5
C11—C12—C7	119.3 (6)	O4—C29—H29B	109.5
C11—C12—C14	119.7 (6)	H29A—C29—H29B	109.5
C7—C12—C14	121.0 (6)	O4—C29—H29C	109.5
C10—C13—H13A	109.5	H29A—C29—H29C	109.5
C10—C13—H13B	109.5	H29B—C29—H29C	109.5
H13A—C13—H13B	109.5	N3—Hg1—N4^i	89.01 (17)
C10—C13—H13C	109.5	N3—Hg1—Br2	97.87 (14)
H13A—C13—H13C	109.5	N4^i—Hg1—Br2	108.12 (13)
H13B—C13—H13C	109.5	N3—Hg1—Br1	104.29 (13)
N1—C14—O1	111.0 (5)	N4^i—Hg1—Br1	99.03 (13)
N1—C14—C12	132.2 (6)	Br2—Hg1—Br1	145.07 (3)
O1—C14—C12	116.8 (5)	C14—N1—N2	107.2 (5)
N2—C15—O1	112.1 (5)	C14—N1—H4A	135.7
N2—C15—C16	130.6 (6)	N2—N1—H4A	116.0
O1—C15—C16	117.3 (5)	C15—N2—N1	106.0 (5)
C21—C16—C17	119.8 (6)	C27—N3—C26	118.1 (5)
C21—C16—C15	123.3 (6)	C27—N3—Hg1	122.5 (4)
C17—C16—C15	116.9 (6)	C26—N3—Hg1	119.4 (4)
C18—C17—C16	120.3 (6)	C1—N4—C5	118.0 (6)
C18—C17—H17	119.8	C1—N4—Hg1^ii	119.2 (4)
C16—C17—H17	119.8	C5—N4—Hg1^ii	122.8 (5)
C19—C18—C17	118.3 (6)	C15—O1—C14	103.7 (5)
C19—C18—C22	122.1 (6)	C21—O2—C23	118.0 (5)
C17—C18—C22	119.6 (7)	C7—O3—C6	118.1 (5)
C18—C19—C20	122.7 (6)	C29—O4—H4A	109.5
N4—C1—C2—C3	−0.2 (10)	C19—C20—C21—C16	1.5 (9)
C1—C2—C3—C4	−0.2 (9)	O2—C23—C24—C25	−4.5 (8)
C1—C2—C3—C6	−179.0 (6)	O2—C23—C24—C28	177.2 (5)
C2—C3—C4—C5	−0.1 (9)	C28—C24—C25—C26	−0.5 (9)
C6—C3—C4—C5	178.7 (6)	C23—C24—C25—C26	−178.9 (6)
C3—C4—C5—N4	0.8 (10)	C24—C25—C26—N3	−0.5 (10)
C2—C3—C6—O3	−126.2 (6)	N3—C27—C28—C24	−1.2 (9)
C4—C3—C6—O3	55.0 (8)	C25—C24—C28—C27	1.3 (9)
O3—C7—C8—C9	−179.1 (6)	C23—C24—C28—C27	179.7 (6)
C12—C7—C8—C9	1.1 (9)	O1—C14—N1—N2	0.2 (6)
C7—C8—C9—C10	−0.2 (10)	C12—C14—N1—N2	179.7 (6)
C8—C9—C10—C11	−0.7 (10)	O1—C14—N1—H4A	−166.9
C8—C9—C10—C13	−179.8 (6)	C12—C14—N1—H4A	12.6
C9—C10—C11—C12	0.7 (9)	O1—C15—N2—N1	0.4 (6)
C13—C10—C11—C12	179.8 (6)	C16—C15—N2—N1	−179.9 (6)
C10—C11—C12—C7	0.3 (9)	C14—N1—N2—C15	−0.4 (6)
C10—C11—C12—C14	179.6 (6)	H4A—N1—N2—C15	169.7
O3—C7—C12—C11	179.1 (5)	C28—C27—N3—C26	0.2 (9)
C8—C7—C12—C11	−1.2 (9)	C28—C27—N3—Hg1	−179.8 (5)
O3—C7—C12—C14	−0.3 (8)	C25—C26—N3—C27	0.6 (9)
C8—C7—C12—C14	179.5 (5)	C25—C26—N3—Hg1	−179.3 (5)
C11—C12—C14—N1	177.6 (6)	N4^i—Hg1—N3—C27	82.2 (5)
C7—C12—C14—N1	−3.1 (10)	Br2—Hg1—N3—C27	−26.0 (5)
C11—C12—C14—O1	−2.9 (8)	Br1—Hg1—N3—C27	−178.7 (4)
C7—C12—C14—O1	176.4 (5)	N4^i—Hg1—N3—C26	−97.8 (5)
N2—C15—C16—C21	4.2 (10)	Br2—Hg1—N3—C26	154.0 (4)
O1—C15—C16—C21	−176.2 (5)	Br1—Hg1—N3—C26	1.3 (5)
N2—C15—C16—C17	−173.6 (6)	C2—C1—N4—C5	0.8 (9)
O1—C15—C16—C17	6.1 (8)	C2—C1—N4—Hg1^ii	−177.7 (5)
C21—C16—C17—C18	0.2 (9)	C4—C5—N4—C1	−1.1 (10)
C15—C16—C17—C18	178.1 (5)	C4—C5—N4—Hg1^ii	177.4 (5)
C16—C17—C18—C19	−0.3 (9)	N2—C15—O1—C14	−0.3 (6)
C16—C17—C18—C22	−179.1 (6)	C16—C15—O1—C14	179.9 (5)
C17—C18—C19—C20	0.9 (10)	N1—C14—O1—C15	0.1 (6)
C22—C18—C19—C20	179.8 (6)	C12—C14—O1—C15	−179.5 (5)
C18—C19—C20—C21	−1.5 (10)	C16—C21—O2—C23	179.7 (5)
C17—C16—C21—O2	−179.0 (5)	C20—C21—O2—C23	1.6 (8)
C15—C16—C21—O2	3.3 (9)	C24—C23—O2—C21	174.8 (5)
C17—C16—C21—C20	−0.8 (9)	C8—C7—O3—C6	9.6 (9)
C15—C16—C21—C20	−178.5 (5)	C12—C7—O3—C6	−170.6 (5)
C19—C20—C21—O2	179.5 (6)	C3—C6—O3—C7	76.8 (7)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N1	0.84	2.04	2.865 (7)	167
O4—H4A···O3	0.84	2.34	2.818 (6)	116

(IV) catena-poly[[[diiodidomercury(II)]-µ-2,5-bis{5-methyl- 2-[(4-pyridyl)methoxy]phenyl}-1,3,4-oxadiazole] methanol monosolvate]

Crystal data

[Hg2I2(C28H24N4O3)]·CH4O	Z = 2
Mr = 950.94	F(000) = 896
Triclinic, P1	Dx = 2.070 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.046 (3) Å	Cell parameters from 2168 reflections
b = 13.153 (4) Å	θ = 2.4–22.1°
c = 13.213 (4) Å	µ = 7.11 mm^−1
α = 95.975 (4)°	T = 298 K
β = 99.503 (4)°	Block, colourless
γ = 97.271 (4)°	0.21 × 0.10 × 0.04 mm
V = 1525.4 (7) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5543 independent reflections
Radiation source: fine-focus sealed tube	4328 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→9
Tmin = 0.317, Tmax = 0.764	k = −15→15
8032 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0321P)^2] where P = (Fo^2 + 2Fc^2)/3
5543 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 1.29 e Å^−3
0 restraints	Δρmin = −1.03 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
I1	0.61915 (7)	0.49150 (5)	1.26739 (4)	0.0630 (2)
I2	0.18974 (7)	0.32120 (5)	1.41435 (5)	0.0632 (2)
C1	0.7947 (10)	0.3845 (6)	0.5172 (6)	0.051 (2)
H1	0.8208	0.4133	0.4601	0.061*
C2	0.9079 (9)	0.3810 (6)	0.5982 (6)	0.047 (2)
H2	1.0067	0.4093	0.5961	0.056*
C3	0.8762 (9)	0.3354 (5)	0.6838 (5)	0.0365 (17)
C4	0.7253 (10)	0.2986 (7)	0.6803 (6)	0.054 (2)
H4	0.6966	0.2674	0.7354	0.064*
C5	0.6173 (10)	0.3071 (7)	0.5973 (7)	0.057 (2)
H5	0.5168	0.2822	0.5985	0.068*
C6	0.9958 (9)	0.3286 (5)	0.7746 (6)	0.0411 (18)
H6A	1.0948	0.3502	0.7584	0.049*
H6B	0.9829	0.3751	0.8334	0.049*
C7	1.0385 (8)	0.1541 (6)	0.7407 (5)	0.0376 (17)
C8	1.1214 (9)	0.1734 (6)	0.6628 (6)	0.048 (2)
H8	1.1465	0.2410	0.6497	0.058*
C9	1.1663 (9)	0.0935 (7)	0.6051 (6)	0.048 (2)
H9	1.2195	0.1085	0.5526	0.058*
C10	1.1349 (9)	−0.0082 (6)	0.6225 (6)	0.0457 (19)
C11	1.0557 (8)	−0.0266 (6)	0.6999 (6)	0.0422 (18)
H11	1.0330	−0.0946	0.7124	0.051*
C12	1.0066 (8)	0.0514 (6)	0.7619 (5)	0.0346 (16)
C13	1.1848 (9)	−0.0928 (7)	0.5577 (7)	0.058 (2)
H13A	1.2070	−0.0685	0.4950	0.087*
H13B	1.1056	−0.1509	0.5411	0.087*
H13C	1.2741	−0.1132	0.5953	0.087*
C14	0.9234 (8)	0.0248 (6)	0.8431 (5)	0.0365 (17)
C15	0.8129 (8)	−0.0765 (6)	0.9323 (5)	0.0373 (17)
C16	0.7627 (8)	−0.1785 (5)	0.9614 (6)	0.0367 (17)
C17	0.8060 (9)	−0.2658 (6)	0.9131 (6)	0.0404 (18)
H17	0.8660	−0.2580	0.8629	0.048*
C18	0.7629 (10)	−0.3645 (6)	0.9369 (6)	0.051 (2)
C19	0.6741 (10)	−0.3730 (6)	1.0119 (6)	0.052 (2)
H19	0.6445	−0.4379	1.0300	0.062*
C20	0.6276 (10)	−0.2873 (6)	1.0611 (6)	0.047 (2)
H20	0.5660	−0.2959	1.1103	0.056*
C21	0.6720 (8)	−0.1892 (6)	1.0376 (5)	0.0382 (17)
C22	0.8147 (11)	−0.4571 (6)	0.8852 (7)	0.064 (3)
H22A	0.8127	−0.4502	0.8133	0.097*
H22B	0.7486	−0.5184	0.8913	0.097*
H22C	0.9162	−0.4620	0.9177	0.097*
C23	0.5409 (9)	−0.1098 (6)	1.1592 (6)	0.0452 (19)
H23A	0.5893	−0.1449	1.2137	0.054*
H23B	0.4428	−0.1498	1.1296	0.054*
C24	0.5211 (8)	−0.0040 (6)	1.2025 (5)	0.0379 (17)
C25	0.5888 (8)	0.0846 (6)	1.1707 (6)	0.0420 (19)
H25	0.6470	0.0803	1.1191	0.050*
C26	0.5680 (9)	0.1800 (6)	1.2176 (6)	0.050 (2)
H26	0.6147	0.2392	1.1964	0.059*
C27	0.4177 (9)	0.1065 (7)	1.3184 (6)	0.048 (2)
H27	0.3562	0.1137	1.3679	0.057*
C28	0.4329 (9)	0.0080 (6)	1.2783 (6)	0.045 (2)
H28	0.3849	−0.0494	1.3017	0.054*
C29	0.7829 (13)	0.3011 (9)	1.0450 (8)	0.085 (3)
H29A	0.8807	0.3149	1.0892	0.127*
H29B	0.7276	0.2389	1.0600	0.127*
H29C	0.7281	0.3577	1.0570	0.127*
Hg1	0.46045 (4)	0.36330 (2)	1.36488 (2)	0.04805 (13)
N1	0.8711 (7)	0.0824 (5)	0.9092 (4)	0.0398 (15)
N2	0.7993 (7)	0.0144 (4)	0.9691 (5)	0.0399 (15)
N3	0.4857 (8)	0.1912 (5)	1.2903 (5)	0.0458 (16)
N4	0.6496 (7)	0.3496 (5)	0.5145 (5)	0.0419 (15)
O1	0.8913 (5)	−0.0780 (4)	0.8520 (4)	0.0383 (12)
O2	0.6315 (6)	−0.1014 (4)	1.0818 (4)	0.0497 (14)
O3	0.9883 (6)	0.2256 (4)	0.8012 (4)	0.0418 (12)
O4	0.8009 (10)	0.2893 (5)	0.9428 (5)	0.083 (2)
H4A	0.8363	0.2359	0.9303	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0726 (4)	0.0573 (4)	0.0576 (4)	−0.0073 (3)	0.0144 (3)	0.0171 (3)
I2	0.0629 (4)	0.0592 (4)	0.0738 (4)	0.0087 (3)	0.0341 (3)	0.0030 (3)
C1	0.059 (6)	0.053 (6)	0.047 (5)	0.012 (4)	0.020 (4)	0.016 (4)
C2	0.049 (5)	0.043 (5)	0.053 (5)	0.012 (4)	0.013 (4)	0.014 (4)
C3	0.052 (5)	0.025 (4)	0.036 (4)	0.012 (3)	0.014 (4)	0.007 (3)
C4	0.051 (5)	0.065 (6)	0.049 (5)	0.007 (4)	0.011 (4)	0.021 (4)
C5	0.045 (5)	0.066 (6)	0.058 (6)	−0.001 (4)	0.009 (4)	0.014 (5)
C6	0.052 (5)	0.027 (4)	0.046 (4)	0.012 (3)	0.010 (4)	0.007 (3)
C7	0.034 (4)	0.042 (5)	0.039 (4)	0.015 (3)	0.005 (3)	0.006 (3)
C8	0.044 (5)	0.046 (5)	0.060 (5)	0.010 (4)	0.019 (4)	0.011 (4)
C9	0.040 (5)	0.064 (6)	0.045 (5)	0.017 (4)	0.014 (4)	0.011 (4)
C10	0.040 (5)	0.045 (5)	0.049 (5)	0.013 (4)	0.001 (4)	−0.005 (4)
C11	0.036 (4)	0.040 (5)	0.048 (5)	0.011 (3)	0.000 (4)	0.001 (4)
C12	0.033 (4)	0.035 (4)	0.034 (4)	0.011 (3)	0.000 (3)	0.000 (3)
C13	0.050 (5)	0.062 (6)	0.063 (6)	0.021 (4)	0.013 (4)	−0.009 (4)
C14	0.043 (4)	0.030 (4)	0.035 (4)	0.008 (3)	0.001 (3)	0.008 (3)
C15	0.036 (4)	0.035 (5)	0.039 (4)	0.006 (3)	0.002 (3)	0.007 (3)
C16	0.032 (4)	0.028 (4)	0.046 (4)	0.005 (3)	−0.002 (3)	0.003 (3)
C17	0.047 (5)	0.035 (5)	0.045 (4)	0.020 (3)	0.008 (4)	0.011 (3)
C18	0.062 (6)	0.034 (5)	0.055 (5)	0.013 (4)	0.000 (4)	0.003 (4)
C19	0.064 (6)	0.033 (5)	0.058 (5)	0.006 (4)	0.007 (4)	0.012 (4)
C20	0.061 (5)	0.033 (5)	0.045 (5)	0.006 (4)	0.007 (4)	0.007 (4)
C21	0.037 (4)	0.039 (5)	0.036 (4)	0.008 (3)	0.001 (3)	0.000 (3)
C22	0.082 (7)	0.027 (5)	0.084 (7)	0.016 (4)	0.012 (6)	−0.001 (4)
C23	0.045 (5)	0.044 (5)	0.045 (5)	0.005 (4)	0.007 (4)	0.003 (4)
C24	0.046 (4)	0.030 (4)	0.037 (4)	0.009 (3)	0.003 (3)	0.003 (3)
C25	0.047 (5)	0.035 (5)	0.048 (5)	0.010 (4)	0.017 (4)	0.004 (4)
C26	0.060 (5)	0.035 (5)	0.060 (5)	0.006 (4)	0.029 (4)	0.006 (4)
C27	0.043 (5)	0.053 (6)	0.051 (5)	0.007 (4)	0.018 (4)	0.004 (4)
C28	0.049 (5)	0.042 (5)	0.043 (4)	0.000 (4)	0.010 (4)	0.009 (4)
C29	0.087 (8)	0.087 (9)	0.086 (8)	0.013 (6)	0.040 (7)	−0.001 (6)
Hg1	0.0548 (2)	0.0410 (2)	0.0514 (2)	0.00717 (15)	0.01765 (15)	0.00725 (14)
N1	0.052 (4)	0.028 (4)	0.038 (3)	0.006 (3)	0.005 (3)	0.001 (3)
N2	0.056 (4)	0.022 (3)	0.046 (4)	0.013 (3)	0.014 (3)	0.008 (3)
N3	0.059 (4)	0.034 (4)	0.047 (4)	0.007 (3)	0.021 (3)	0.002 (3)
N4	0.046 (4)	0.039 (4)	0.042 (4)	0.009 (3)	0.011 (3)	0.004 (3)
O1	0.044 (3)	0.026 (3)	0.045 (3)	0.008 (2)	0.007 (2)	0.003 (2)
O2	0.064 (4)	0.034 (3)	0.058 (3)	0.012 (3)	0.026 (3)	0.005 (3)
O3	0.056 (3)	0.031 (3)	0.043 (3)	0.011 (2)	0.016 (3)	0.010 (2)
O4	0.136 (7)	0.055 (5)	0.080 (5)	0.040 (4)	0.061 (5)	0.018 (3)

Geometric parameters (Å, º)

I1—Hg1	2.6482 (7)	C16—C21	1.406 (10)
I2—Hg1	2.6440 (9)	C17—C18	1.390 (10)
C1—N4	1.328 (10)	C17—H17	0.9300
C1—C2	1.362 (11)	C18—C19	1.379 (11)
C1—H1	0.9300	C18—C22	1.500 (11)
C2—C3	1.388 (10)	C19—C20	1.389 (11)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.380 (11)	C20—C21	1.385 (10)
C3—C6	1.495 (10)	C20—H20	0.9300
C4—C5	1.367 (12)	C21—O2	1.358 (9)
C4—H4	0.9300	C22—H22A	0.9600
C5—N4	1.337 (10)	C22—H22B	0.9600
C5—H5	0.9300	C22—H22C	0.9600
C6—O3	1.431 (8)	C23—O2	1.417 (8)
C6—H6A	0.9700	C23—C24	1.492 (10)
C6—H6B	0.9700	C23—H23A	0.9700
C7—O3	1.343 (8)	C23—H23B	0.9700
C7—C8	1.395 (10)	C24—C25	1.384 (10)
C7—C12	1.411 (10)	C24—C28	1.388 (10)
C8—C9	1.376 (11)	C25—C26	1.389 (10)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.384 (11)	C26—N3	1.317 (9)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.367 (10)	C27—N3	1.321 (10)
C10—C13	1.493 (10)	C27—C28	1.380 (11)
C11—C12	1.407 (10)	C27—H27	0.9300
C11—H11	0.9300	C28—H28	0.9300
C12—C14	1.456 (9)	C29—O4	1.383 (10)
C13—H13A	0.9600	C29—H29A	0.9600
C13—H13B	0.9600	C29—H29B	0.9600
C13—H13C	0.9600	C29—H29C	0.9600
C14—N1	1.285 (9)	Hg1—N3	2.427 (6)
C14—O1	1.368 (8)	Hg1—N4^i	2.429 (6)
C15—N2	1.272 (9)	N1—N2	1.421 (8)
C15—O1	1.370 (8)	N4—Hg1^ii	2.429 (6)
C15—C16	1.472 (10)	O4—H4A	0.8200
C16—C17	1.387 (10)
N4—C1—C2	124.4 (7)	C18—C19—H19	119.1
N4—C1—H1	117.8	C20—C19—H19	119.1
C2—C1—H1	117.8	C21—C20—C19	120.6 (8)
C1—C2—C3	120.2 (7)	C21—C20—H20	119.7
C1—C2—H2	119.9	C19—C20—H20	119.7
C3—C2—H2	119.9	O2—C21—C20	124.4 (7)
C4—C3—C2	115.1 (7)	O2—C21—C16	117.0 (6)
C4—C3—C6	122.2 (6)	C20—C21—C16	118.5 (7)
C2—C3—C6	122.6 (7)	C18—C22—H22A	109.5
C5—C4—C3	121.3 (7)	C18—C22—H22B	109.5
C5—C4—H4	119.3	H22A—C22—H22B	109.5
C3—C4—H4	119.3	C18—C22—H22C	109.5
N4—C5—C4	123.0 (8)	H22A—C22—H22C	109.5
N4—C5—H5	118.5	H22B—C22—H22C	109.5
C4—C5—H5	118.5	O2—C23—C24	109.0 (6)
O3—C6—C3	111.3 (6)	O2—C23—H23A	109.9
O3—C6—H6A	109.4	C24—C23—H23A	109.9
C3—C6—H6A	109.4	O2—C23—H23B	109.9
O3—C6—H6B	109.4	C24—C23—H23B	109.9
C3—C6—H6B	109.4	H23A—C23—H23B	108.3
H6A—C6—H6B	108.0	C25—C24—C28	117.6 (7)
O3—C7—C8	125.8 (7)	C25—C24—C23	122.5 (7)
O3—C7—C12	115.5 (6)	C28—C24—C23	119.9 (7)
C8—C7—C12	118.7 (7)	C24—C25—C26	118.7 (7)
C9—C8—C7	120.7 (8)	C24—C25—H25	120.7
C9—C8—H8	119.7	C26—C25—H25	120.7
C7—C8—H8	119.7	N3—C26—C25	123.6 (7)
C8—C9—C10	122.2 (7)	N3—C26—H26	118.2
C8—C9—H9	118.9	C25—C26—H26	118.2
C10—C9—H9	118.9	N3—C27—C28	123.5 (7)
C11—C10—C9	116.9 (7)	N3—C27—H27	118.3
C11—C10—C13	122.6 (8)	C28—C27—H27	118.3
C9—C10—C13	120.5 (8)	C27—C28—C24	119.0 (7)
C10—C11—C12	123.8 (7)	C27—C28—H28	120.5
C10—C11—H11	118.1	C24—C28—H28	120.5
C12—C11—H11	118.1	O4—C29—H29A	109.5
C11—C12—C7	117.7 (7)	O4—C29—H29B	109.5
C11—C12—C14	120.1 (7)	H29A—C29—H29B	109.5
C7—C12—C14	122.2 (6)	O4—C29—H29C	109.5
C10—C13—H13A	109.5	H29A—C29—H29C	109.5
C10—C13—H13B	109.5	H29B—C29—H29C	109.5
H13A—C13—H13B	109.5	N3—Hg1—N4^i	90.0 (2)
C10—C13—H13C	109.5	N3—Hg1—I2	98.62 (15)
H13A—C13—H13C	109.5	N4^i—Hg1—I2	108.08 (14)
H13B—C13—H13C	109.5	N3—Hg1—I1	105.39 (14)
N1—C14—O1	112.5 (6)	N4^i—Hg1—I1	100.77 (14)
N1—C14—C12	130.7 (7)	I2—Hg1—I1	142.20 (3)
O1—C14—C12	116.8 (6)	C14—N1—N2	106.0 (6)
N2—C15—O1	113.0 (6)	C14—N1—H4A	136.4
N2—C15—C16	131.9 (7)	N2—N1—H4A	116.5
O1—C15—C16	115.2 (6)	C15—N2—N1	106.2 (6)
C17—C16—C21	119.4 (7)	C26—N3—C27	117.6 (7)
C17—C16—C15	119.4 (7)	C26—N3—Hg1	119.7 (5)
C21—C16—C15	121.3 (7)	C27—N3—Hg1	122.6 (5)
C16—C17—C18	122.4 (7)	C1—N4—C5	115.9 (7)
C16—C17—H17	118.8	C1—N4—Hg1^ii	120.4 (5)
C18—C17—H17	118.8	C5—N4—Hg1^ii	123.7 (5)
C19—C18—C17	117.2 (8)	C14—O1—C15	102.3 (5)
C19—C18—C22	121.7 (8)	C21—O2—C23	118.2 (6)
C17—C18—C22	121.2 (8)	C7—O3—C6	118.6 (6)
C18—C19—C20	121.9 (7)	C29—O4—H4A	109.5
N4—C1—C2—C3	2.4 (13)	C15—C16—C21—C20	179.6 (7)
C1—C2—C3—C4	−1.8 (12)	O2—C23—C24—C25	−2.1 (10)
C1—C2—C3—C6	179.5 (7)	O2—C23—C24—C28	178.4 (7)
C2—C3—C4—C5	0.2 (12)	C28—C24—C25—C26	1.4 (11)
C6—C3—C4—C5	178.9 (8)	C23—C24—C25—C26	−178.0 (7)
C3—C4—C5—N4	1.0 (14)	C24—C25—C26—N3	−0.7 (13)
C4—C3—C6—O3	51.6 (10)	N3—C27—C28—C24	−1.6 (13)
C2—C3—C6—O3	−129.8 (7)	C25—C24—C28—C27	−0.4 (11)
O3—C7—C8—C9	−179.6 (7)	C23—C24—C28—C27	179.1 (7)
C12—C7—C8—C9	2.4 (12)	O1—C14—N1—N2	0.8 (8)
C7—C8—C9—C10	−1.4 (13)	C12—C14—N1—N2	179.7 (7)
C8—C9—C10—C11	0.4 (12)	O1—C14—N1—H4A	−166.5
C8—C9—C10—C13	179.7 (8)	C12—C14—N1—H4A	12.4
C9—C10—C11—C12	−0.4 (11)	O1—C15—N2—N1	1.0 (8)
C13—C10—C11—C12	−179.7 (7)	C16—C15—N2—N1	179.8 (7)
C10—C11—C12—C7	1.5 (11)	C14—N1—N2—C15	−1.1 (8)
C10—C11—C12—C14	−179.7 (7)	H4A—N1—N2—C15	169.1
O3—C7—C12—C11	179.4 (6)	C25—C26—N3—C27	−1.2 (13)
C8—C7—C12—C11	−2.4 (10)	C25—C26—N3—Hg1	179.9 (6)
O3—C7—C12—C14	0.6 (10)	C28—C27—N3—C26	2.4 (13)
C8—C7—C12—C14	178.8 (7)	C28—C27—N3—Hg1	−178.7 (6)
C11—C12—C14—N1	178.4 (7)	N4^i—Hg1—N3—C26	−100.6 (7)
C7—C12—C14—N1	−2.8 (12)	I2—Hg1—N3—C26	151.1 (6)
C11—C12—C14—O1	−2.7 (10)	I1—Hg1—N3—C26	0.6 (7)
C7—C12—C14—O1	176.0 (6)	N4^i—Hg1—N3—C27	80.6 (7)
N2—C15—C16—C17	−174.0 (8)	I2—Hg1—N3—C27	−27.7 (7)
O1—C15—C16—C17	4.7 (10)	I1—Hg1—N3—C27	−178.2 (6)
N2—C15—C16—C21	5.8 (13)	C2—C1—N4—C5	−1.2 (12)
O1—C15—C16—C21	−175.4 (6)	C2—C1—N4—Hg1^ii	179.3 (6)
C21—C16—C17—C18	0.0 (11)	C4—C5—N4—C1	−0.5 (13)
C15—C16—C17—C18	179.9 (7)	C4—C5—N4—Hg1^ii	179.0 (7)
C16—C17—C18—C19	−0.1 (12)	N1—C14—O1—C15	−0.2 (8)
C16—C17—C18—C22	−178.4 (8)	C12—C14—O1—C15	−179.3 (6)
C17—C18—C19—C20	0.7 (13)	N2—C15—O1—C14	−0.5 (8)
C22—C18—C19—C20	179.1 (8)	C16—C15—O1—C14	−179.5 (6)
C18—C19—C20—C21	−1.3 (13)	C20—C21—O2—C23	1.7 (11)
C19—C20—C21—O2	179.9 (7)	C16—C21—O2—C23	−179.6 (6)
C19—C20—C21—C16	1.2 (12)	C24—C23—O2—C21	175.4 (6)
C17—C16—C21—O2	−179.3 (7)	C8—C7—O3—C6	11.3 (11)
C15—C16—C21—O2	0.8 (10)	C12—C7—O3—C6	−170.6 (6)
C17—C16—C21—C20	−0.6 (11)	C3—C6—O3—C7	74.6 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N1	0.82	2.08	2.878 (9)	164
O4—H4A···O3	0.82	2.36	2.855 (8)	119