Bis(μ-N,N'-di-3-pyridyl-2,6-pyridine-2,6-dicarboxamide-κN:N')bis[dibrom-ido-mercury(II)] N,N-dimethyl-formamide disolvate.

In the dinuclear centrosymmetric title complex, [Hg(2)Br(4)(C(17)H(13)N(5)O(2))(2)]·2C(3)H(7)NO, the Hg(II) atom is coordinated by two Br atoms and two N atoms from two different ligands in a distorted tetra-hedral geometry. The solvent mol-ecule is linked to the 28-atom ring by two hydrogen bonds.

Related literature

For related literature, see: Baer et al. (2002 ▶); Chae et al. (2004 ▶ and references cited therein); Qin et al. (2003 ▶).

Experimental

Crystal data

[Hg2Br4(C17H13N5O2)2]·2C3H7NO

M = 1505.62

Triclinic,

a = 7.7609 (16) Å

b = 12.267 (3) Å

c = 13.296 (3) Å

α = 92.27 (3)°

β = 105.82 (3)°

γ = 104.07 (3)°

V = 1173.7 (4) Å3

Z = 1

Mo Kα radiation

μ = 10.00 mm−1

T = 293 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.240, T max = 0.281 (expected range = 0.156–0.183)

14249 measured reflections

5337 independent reflections

4364 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.067

S = 1.03

5337 reflections

299 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.71 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028754/ng2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028754/ng2488Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

[Hg2Br4(C17H13N5O2)2]·2C3H7NO	Z = 1
Mr = 1505.62	F(000) = 712
Triclinic, P1	Dx = 2.130 Mg m−3
a = 7.7609 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.267 (3) Å	Cell parameters from 3306 reflections
c = 13.296 (3) Å	θ = 3.2–27.5°
α = 92.27 (3)°	µ = 10.00 mm−1
β = 105.82 (3)°	T = 293 K
γ = 104.07 (3)°	Prism, colourless
V = 1173.7 (4) Å3	0.20 × 0.18 × 0.17 mm

Rigaku Saturn724 diffractometer	5337 independent reflections
Radiation source: fine-focus sealed tube	4364 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
dtprofit.ref scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −15→15
Tmin = 0.240, Tmax = 0.281	l = −17→17
14249 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0274P)2] where P = (Fo2 + 2Fc2)/3
5337 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.61 e Å−3
2 restraints	Δρmin = −0.71 e Å−3

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.

	x	y	z	Uiso*/Ueq
Hg1	0.35413 (3)	0.143038 (15)	0.325732 (13)	0.04901 (8)
Br1	0.37301 (7)	−0.05158 (4)	0.27313 (4)	0.05602 (14)
Br2	0.63842 (7)	0.30874 (4)	0.39232 (4)	0.06222 (15)
O1	0.8838 (6)	0.5153 (3)	1.1145 (3)	0.0790 (12)
O2	0.1707 (5)	0.0697 (3)	0.7966 (2)	0.0565 (9)
N1	0.8086 (5)	0.7906 (3)	0.8251 (3)	0.0394 (8)
N2	0.7259 (5)	0.5300 (3)	0.9465 (3)	0.0399 (9)
N3	0.5289 (5)	0.3133 (3)	0.9248 (2)	0.0342 (8)
N4	0.3039 (5)	0.2237 (3)	0.7291 (3)	0.0375 (8)
N5	0.1886 (5)	0.1582 (3)	0.4441 (3)	0.0388 (8)
C1	0.9457 (6)	0.8600 (4)	0.9012 (3)	0.0410 (11)
H1	0.9948	0.9335	0.8888	0.049*
C2	1.0151 (6)	0.8257 (4)	0.9966 (3)	0.0458 (11)
H2	1.1084	0.8766	1.0485	0.055*
C3	0.9496 (6)	0.7169 (4)	1.0172 (3)	0.0429 (11)
H3	0.9979	0.6935	1.0822	0.051*
C4	0.8082 (6)	0.6423 (3)	0.9377 (3)	0.0323 (9)
C5	0.7417 (6)	0.6847 (3)	0.8436 (3)	0.0356 (10)
H5	0.6454	0.6369	0.7907	0.043*
C6	0.7650 (6)	0.4739 (4)	1.0323 (3)	0.0423 (11)
C7	0.6516 (6)	0.3533 (3)	1.0186 (3)	0.0376 (10)
C8	0.6773 (7)	0.2900 (4)	1.1030 (3)	0.0466 (12)
H8	0.7648	0.3211	1.1670	0.056*
C9	0.5708 (7)	0.1802 (4)	1.0900 (3)	0.0477 (12)
H9	0.5851	0.1356	1.1451	0.057*
C10	0.4421 (6)	0.1373 (4)	0.9935 (4)	0.0421 (11)
H10	0.3679	0.0633	0.9827	0.050*
C11	0.4256 (6)	0.2061 (3)	0.9135 (3)	0.0353 (10)
C12	0.2874 (6)	0.1602 (3)	0.8079 (3)	0.0380 (10)
C13	0.1959 (6)	0.1874 (3)	0.6234 (3)	0.0352 (10)
C14	0.0045 (6)	0.1485 (3)	0.5954 (4)	0.0418 (11)
H14	−0.0582	0.1444	0.6462	0.050*
C15	−0.0910 (6)	0.1160 (4)	0.4913 (4)	0.0468 (12)
H15	−0.2198	0.0901	0.4707	0.056*
C16	0.0035 (7)	0.1218 (4)	0.4176 (4)	0.0463 (11)
H16	−0.0629	0.0998	0.3472	0.056*
C17	0.2825 (6)	0.1910 (3)	0.5445 (3)	0.0343 (9)
H17	0.4111	0.2175	0.5627	0.041*
H22	0.396 (4)	0.283 (2)	0.745 (3)	0.044 (13)*
H21	0.642 (4)	0.491 (3)	0.8924 (19)	0.039 (12)*
O3	0.4162 (5)	0.5774 (3)	0.2838 (2)	0.0568 (9)
N6	0.1662 (6)	0.5374 (3)	0.3463 (3)	0.0465 (10)
C18	−0.0003 (7)	0.5662 (5)	0.3550 (4)	0.0653 (15)
H18A	−0.0186	0.6282	0.3152	0.098*
H18B	0.0132	0.5875	0.4275	0.098*
H18C	−0.1054	0.5019	0.3280	0.098*
C19	0.2125 (9)	0.4419 (4)	0.3969 (4)	0.0719 (17)
H19A	0.3199	0.4287	0.3813	0.108*
H19B	0.1099	0.3759	0.3715	0.108*
H19C	0.2385	0.4576	0.4716	0.108*
C20	0.2735 (8)	0.5963 (4)	0.2962 (3)	0.0503 (12)
H20A	0.2392	0.6583	0.2671	0.060*

	U11	U22	U33	U12	U13	U23
Hg1	0.06762 (15)	0.04080 (12)	0.03641 (11)	0.01450 (9)	0.01118 (9)	0.00594 (8)
Br1	0.0631 (3)	0.0433 (3)	0.0679 (3)	0.0189 (2)	0.0251 (3)	0.0047 (2)
Br2	0.0546 (3)	0.0547 (3)	0.0623 (3)	0.0063 (3)	0.0000 (3)	0.0042 (3)
O1	0.105 (3)	0.053 (2)	0.039 (2)	−0.011 (2)	−0.016 (2)	0.0158 (17)
O2	0.067 (2)	0.0389 (18)	0.049 (2)	−0.0133 (17)	0.0173 (17)	0.0083 (16)
N1	0.044 (2)	0.035 (2)	0.0344 (19)	0.0063 (17)	0.0071 (17)	0.0039 (16)
N2	0.047 (2)	0.037 (2)	0.0269 (19)	0.0029 (18)	0.0026 (17)	0.0033 (17)
N3	0.041 (2)	0.0331 (19)	0.0315 (19)	0.0101 (16)	0.0143 (16)	0.0078 (16)
N4	0.042 (2)	0.0298 (19)	0.034 (2)	−0.0031 (17)	0.0113 (17)	0.0018 (16)
N5	0.048 (2)	0.0330 (19)	0.0318 (19)	0.0080 (17)	0.0082 (17)	0.0027 (16)
C1	0.044 (3)	0.031 (2)	0.045 (3)	0.004 (2)	0.013 (2)	0.005 (2)
C2	0.045 (3)	0.043 (3)	0.036 (2)	−0.002 (2)	0.001 (2)	0.001 (2)
C3	0.044 (3)	0.040 (3)	0.035 (2)	0.006 (2)	0.001 (2)	0.004 (2)
C4	0.036 (2)	0.031 (2)	0.028 (2)	0.0082 (18)	0.0086 (18)	0.0045 (17)
C5	0.040 (3)	0.033 (2)	0.027 (2)	0.0048 (19)	0.0043 (19)	0.0013 (18)
C6	0.052 (3)	0.040 (3)	0.030 (2)	0.010 (2)	0.005 (2)	0.010 (2)
C7	0.046 (3)	0.038 (2)	0.033 (2)	0.013 (2)	0.014 (2)	0.011 (2)
C8	0.056 (3)	0.051 (3)	0.036 (2)	0.014 (2)	0.016 (2)	0.012 (2)
C9	0.060 (3)	0.048 (3)	0.038 (3)	0.014 (2)	0.018 (2)	0.018 (2)
C10	0.052 (3)	0.034 (2)	0.050 (3)	0.013 (2)	0.027 (2)	0.012 (2)
C11	0.044 (3)	0.030 (2)	0.036 (2)	0.0066 (19)	0.021 (2)	0.0063 (18)
C12	0.044 (3)	0.032 (2)	0.042 (3)	0.009 (2)	0.020 (2)	0.004 (2)
C13	0.039 (3)	0.027 (2)	0.038 (2)	0.0062 (18)	0.011 (2)	0.0052 (18)
C14	0.041 (3)	0.033 (2)	0.054 (3)	0.010 (2)	0.018 (2)	0.006 (2)
C15	0.040 (3)	0.032 (2)	0.060 (3)	0.007 (2)	0.003 (2)	0.004 (2)
C16	0.057 (3)	0.033 (2)	0.042 (3)	0.014 (2)	0.000 (2)	0.004 (2)
C17	0.036 (2)	0.032 (2)	0.032 (2)	0.0054 (18)	0.0080 (19)	0.0023 (18)
O3	0.059 (2)	0.053 (2)	0.052 (2)	−0.0049 (18)	0.0235 (18)	0.0038 (17)
N6	0.058 (3)	0.038 (2)	0.044 (2)	0.0050 (19)	0.021 (2)	0.0033 (18)
C18	0.063 (4)	0.070 (4)	0.063 (4)	0.018 (3)	0.022 (3)	−0.010 (3)
C19	0.104 (5)	0.049 (3)	0.080 (4)	0.024 (3)	0.048 (4)	0.023 (3)
C20	0.065 (3)	0.041 (3)	0.036 (3)	0.002 (3)	0.010 (3)	0.000 (2)

Hg1—N5	2.315 (3)	C7—C8	1.386 (6)
Hg1—N1i	2.351 (3)	C8—C9	1.374 (6)
Hg1—Br1	2.5108 (8)	C8—H8	0.9300
Hg1—Br2	2.5289 (12)	C9—C10	1.383 (6)
O1—C6	1.218 (5)	C9—H9	0.9300
O2—C12	1.225 (5)	C10—C11	1.382 (6)
N1—C5	1.335 (5)	C10—H10	0.9300
N1—C1	1.337 (5)	C11—C12	1.503 (6)
N1—Hg1i	2.351 (3)	C13—C14	1.384 (6)
N2—C6	1.357 (5)	C13—C17	1.389 (5)
N2—C4	1.394 (5)	C14—C15	1.369 (6)
N2—H21	0.856 (10)	C14—H14	0.9300
N3—C7	1.334 (5)	C15—C16	1.370 (6)
N3—C11	1.342 (5)	C15—H15	0.9300
N4—C12	1.346 (5)	C16—H16	0.9300
N4—C13	1.414 (5)	C17—H17	0.9300
N4—H22	0.859 (10)	O3—C20	1.236 (6)
N5—C17	1.326 (5)	N6—C20	1.306 (6)
N5—C16	1.337 (6)	N6—C19	1.446 (6)
C1—C2	1.361 (6)	N6—C18	1.452 (6)
C1—H1	0.9300	C18—H18A	0.9600
C2—C3	1.374 (6)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C3—C4	1.401 (5)	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.390 (5)	C19—H19C	0.9600
C5—H5	0.9300	C20—H20A	0.9300
C6—C7	1.502 (6)
N5—Hg1—N1i	103.47 (12)	C8—C9—H9	120.6
N5—Hg1—Br1	117.00 (9)	C10—C9—H9	120.6
N1i—Hg1—Br1	107.93 (9)	C11—C10—C9	118.8 (4)
N5—Hg1—Br2	102.81 (9)	C11—C10—H10	120.6
N1i—Hg1—Br2	100.41 (9)	C9—C10—H10	120.6
Br1—Hg1—Br2	122.54 (3)	N3—C11—C10	123.1 (4)
C5—N1—C1	118.4 (4)	N3—C11—C12	117.5 (3)
C5—N1—Hg1i	118.6 (3)	C10—C11—C12	119.4 (4)
C1—N1—Hg1i	122.0 (3)	O2—C12—N4	123.6 (4)
C6—N2—C4	126.9 (4)	O2—C12—C11	120.7 (4)
C6—N2—H21	116 (3)	N4—C12—C11	115.7 (4)
C4—N2—H21	118 (3)	C14—C13—C17	118.3 (4)
C7—N3—C11	117.1 (3)	C14—C13—N4	122.0 (4)
C12—N4—C13	122.6 (4)	C17—C13—N4	119.8 (4)
C12—N4—H22	116 (3)	C15—C14—C13	118.7 (4)
C13—N4—H22	121 (3)	C15—C14—H14	120.7
C17—N5—C16	118.9 (4)	C13—C14—H14	120.7
C17—N5—Hg1	118.2 (3)	C14—C15—C16	119.9 (4)
C16—N5—Hg1	122.4 (3)	C14—C15—H15	120.0
N1—C1—C2	121.6 (4)	C16—C15—H15	120.0
N1—C1—H1	119.2	N5—C16—C15	121.8 (4)
C2—C1—H1	119.2	N5—C16—H16	119.1
C1—C2—C3	121.0 (4)	C15—C16—H16	119.1
C1—C2—H2	119.5	N5—C17—C13	122.5 (4)
C3—C2—H2	119.5	N5—C17—H17	118.8
C2—C3—C4	118.2 (4)	C13—C17—H17	118.8
C2—C3—H3	120.9	C20—N6—C19	120.5 (4)
C4—C3—H3	120.9	C20—N6—C18	121.7 (4)
C5—C4—N2	117.6 (4)	C19—N6—C18	117.7 (4)
C5—C4—C3	117.2 (4)	N6—C18—H18A	109.5
N2—C4—C3	125.2 (4)	N6—C18—H18B	109.5
N1—C5—C4	123.5 (4)	H18A—C18—H18B	109.5
N1—C5—H5	118.2	N6—C18—H18C	109.5
C4—C5—H5	118.2	H18A—C18—H18C	109.5
O1—C6—N2	124.0 (4)	H18B—C18—H18C	109.5
O1—C6—C7	121.1 (4)	N6—C19—H19A	109.5
N2—C6—C7	114.9 (4)	N6—C19—H19B	109.5
N3—C7—C8	123.5 (4)	H19A—C19—H19B	109.5
N3—C7—C6	117.3 (3)	N6—C19—H19C	109.5
C8—C7—C6	119.2 (4)	H19A—C19—H19C	109.5
C9—C8—C7	118.7 (4)	H19B—C19—H19C	109.5
C9—C8—H8	120.7	O3—C20—N6	126.2 (5)
C7—C8—H8	120.7	O3—C20—H20A	116.9
C8—C9—C10	118.8 (4)	N6—C20—H20A	116.9
N1i—Hg1—N5—C17	−141.8 (3)	C6—C7—C8—C9	179.1 (4)
Br1—Hg1—N5—C17	99.7 (3)	C7—C8—C9—C10	−0.1 (7)
Br2—Hg1—N5—C17	−37.6 (3)	C8—C9—C10—C11	0.2 (7)
N1i—Hg1—N5—C16	46.8 (3)	C7—N3—C11—C10	−0.3 (6)
Br1—Hg1—N5—C16	−71.7 (3)	C7—N3—C11—C12	−179.8 (3)
Br2—Hg1—N5—C16	151.0 (3)	C9—C10—C11—N3	0.0 (6)
C5—N1—C1—C2	−1.1 (6)	C9—C10—C11—C12	179.5 (4)
Hg1i—N1—C1—C2	167.2 (3)	C13—N4—C12—O2	−4.8 (7)
N1—C1—C2—C3	1.6 (7)	C13—N4—C12—C11	174.0 (4)
C1—C2—C3—C4	−0.5 (7)	N3—C11—C12—O2	−169.3 (4)
C6—N2—C4—C5	−177.3 (4)	C10—C11—C12—O2	11.2 (6)
C6—N2—C4—C3	0.9 (7)	N3—C11—C12—N4	11.9 (6)
C2—C3—C4—C5	−1.1 (6)	C10—C11—C12—N4	−167.7 (4)
C2—C3—C4—N2	−179.4 (4)	C12—N4—C13—C14	51.7 (6)
C1—N1—C5—C4	−0.7 (6)	C12—N4—C13—C17	−128.8 (4)
Hg1i—N1—C5—C4	−169.4 (3)	C17—C13—C14—C15	−0.4 (6)
N2—C4—C5—N1	−179.9 (4)	N4—C13—C14—C15	179.2 (4)
C3—C4—C5—N1	1.8 (6)	C13—C14—C15—C16	0.5 (6)
C4—N2—C6—O1	−1.7 (8)	C17—N5—C16—C15	−1.0 (6)
C4—N2—C6—C7	179.3 (4)	Hg1—N5—C16—C15	170.4 (3)
C11—N3—C7—C8	0.4 (6)	C14—C15—C16—N5	0.2 (7)
C11—N3—C7—C6	−178.9 (4)	C16—N5—C17—C13	1.0 (6)
O1—C6—C7—N3	−177.7 (4)	Hg1—N5—C17—C13	−170.7 (3)
N2—C6—C7—N3	1.3 (6)	C14—C13—C17—N5	−0.3 (6)
O1—C6—C7—C8	3.0 (7)	N4—C13—C17—N5	−179.9 (4)
N2—C6—C7—C8	−178.0 (4)	C19—N6—C20—O3	2.1 (7)
N3—C7—C8—C9	−0.2 (7)	C18—N6—C20—O3	−179.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H22···O3i	0.86 (1)	2.08 (2)	2.891 (5)	157 (4)
N2—H21···O3i	0.86 (1)	2.34 (2)	3.076 (5)	144 (3)
N2—H21···N3	0.86 (1)	2.25 (4)	2.685 (5)	111 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H22⋯O3i	0.859 (10)	2.08 (2)	2.891 (5)	157 (4)
N2—H21⋯O3i	0.856 (10)	2.34 (2)	3.076 (5)	144 (3)
N2—H21⋯N3	0.856 (10)	2.25 (4)	2.685 (5)	111 (3)

Symmetry code: (i) .