Crystal structure of di-μ-chlorido-bis(chlorido-{N (1)-phenyl-N (4)-[(pyridin-2-yl-κN)methyl-idene]benzene-1,4-di-amine-κN (4)}mercury(II)).

The whole mol-ecule of the title complex, [Hg2Cl4(C18H15N3)2], is generated by inversion symmetry. It was synthesized from the pyridine-derived Schiff base N-phenyl-N'-[(pyridin-2-yl)methyl-idene]benzene-1,4-di-amine (PPMBD). The five-coordinated Hg(2+) ions have a distorted square-pyramidal environment defined by two N atoms, viz. the imine and the other pyridyl [Hg-N = 2.467 (6) and 2.310 (6) Å, respectively] belonging to the bidentate imino-pyridine ligand, and three Cl atoms [Hg-Cl = 2.407 (2), 2.447 (2) and 3.031 (2) Å]. The longest Hg-Cl bond is bridging about the inversion centre. In the ligand, the central ring and pyridine ring are oriented at a dihedral angle of 8.1 (4)°, while the planes of the pyridine ring and the terminal phenyl ring are oriented at a dihedral angle of 53.8 (4)°. In the crystal, mol-ecules are linked by N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming sheets parallel to (001).

Related literature

For applications of pyridincarbaldehyde and related structures, see: Baul et al. (2004 ▸); Das et al. (2013 ▸); Faizi & Sen (2014 ▸); Hughes & Prince (1978 ▸); Jursic et al. (2002 ▸); Kasselouri et al. (1993 ▸); Mandal et al. (2012 ▸); Motswainyana et al. (2013 ▸); Song et al. (2011 ▸).

Experimental

Crystal data

[Hg2Cl4(C18H15N3)2]

M = 1089.64

Monoclinic,

a = 11.7507 (14) Å

b = 8.9026 (11) Å

c = 17.050 (2) Å

β = 90.194 (8)°

V = 1783.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 8.93 mm−1

T = 100 K

0.18 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▸) T min = 0.296, T max = 0.414

19428 measured reflections

4451 independent reflections

2451 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.124

S = 0.96

4451 reflections

220 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.78 e Å−3

Δρmin = −1.13 e Å−3

Data collection: SMART (Bruker, 2003 ▸); cell refinement: SAINT (Bruker, 2003 ▸); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015015790/su5192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015015790/su5192Isup2.hkl

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015015790/su5192fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The unlabelled atoms are related to the labelled atoms by inversion symmetry (symmetry code: −x + 1, −y + 1, −z + 1).

Click here for additional data file.

c . DOI: 10.1107/S2056989015015790/su5192fig2.tif

The crystal packing of the title compound viewed along the c axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details), and for clarity only the H atoms involved in hydrogen bonding are shown.

CCDC reference: 1420119

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Hg2Cl4(C18H15N3)2]	Z = 2
Mr = 1089.64	F(000) = 1032
Monoclinic, P21/c	Dx = 2.029 Mg m−3
a = 11.7507 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9026 (11) Å	µ = 8.93 mm−1
c = 17.050 (2) Å	T = 100 K
β = 90.194 (8)°	Needle, yellow
V = 1783.6 (4) Å3	0.18 × 0.15 × 0.12 mm

Bruker SMART APEX CCD diffractometer	4451 independent reflections
Radiation source: fine-focus sealed tube	2451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
/w–scans	θmax = 28.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→15
Tmin = 0.296, Tmax = 0.414	k = −11→11
19428 measured reflections	l = −22→22

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0446P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
4451 reflections	Δρmax = 1.78 e Å−3
220 parameters	Δρmin = −1.13 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
Hg1	0.60187 (3)	0.67045 (4)	0.53562 (2)	0.06131 (16)
Cl1	0.50851 (17)	0.6189 (2)	0.40995 (11)	0.0574 (5)
Cl2	0.78086 (16)	0.5540 (2)	0.56798 (12)	0.0631 (5)
N1	0.4820 (5)	0.7921 (7)	0.6219 (4)	0.0525 (16)
N2	0.6534 (5)	0.9389 (7)	0.5409 (3)	0.0474 (15)
N3	1.0303 (6)	1.1588 (8)	0.3773 (4)	0.0633 (19)
H3N	1.072 (6)	1.223 (8)	0.403 (4)	0.076*
C1	0.3949 (7)	0.7282 (10)	0.6584 (5)	0.068 (2)
H1	0.3772	0.6263	0.6471	0.082*
C2	0.3290 (7)	0.8051 (10)	0.7125 (5)	0.066 (2)
H2	0.2672	0.7562	0.7375	0.079*
C3	0.3529 (7)	0.9481 (11)	0.7291 (5)	0.065 (2)
H3	0.3106	1.0011	0.7677	0.078*
C4	0.4402 (7)	1.0173 (11)	0.6891 (4)	0.064 (2)
H4	0.4569	1.1203	0.6983	0.076*
C5	0.5036 (6)	0.9358 (9)	0.6355 (4)	0.0473 (18)
C6	0.5981 (6)	1.0109 (10)	0.5924 (4)	0.057 (2)
H6	0.6168	1.1125	0.6035	0.069*
C7	0.7473 (6)	0.9994 (10)	0.4998 (4)	0.0543 (19)
C8	0.7938 (7)	1.1435 (9)	0.5152 (5)	0.060 (2)
H8	0.7601	1.2064	0.5537	0.073*
C9	0.8865 (7)	1.1914 (10)	0.4749 (4)	0.063 (2)
H9	0.9190	1.2863	0.4870	0.076*
C10	0.9349 (6)	1.1035 (10)	0.4159 (4)	0.054 (2)
C11	0.8901 (7)	0.9631 (10)	0.3999 (4)	0.057 (2)
H11	0.9231	0.9016	0.3605	0.069*
C12	0.7970 (7)	0.9128 (9)	0.4417 (4)	0.055 (2)
H12	0.7663	0.8164	0.4302	0.066*
C13	1.0727 (7)	1.1208 (9)	0.3032 (4)	0.055 (2)
C14	1.1864 (7)	1.1437 (9)	0.2874 (5)	0.056 (2)
H14	1.2346	1.1839	0.3270	0.067*
C15	1.2311 (7)	1.1094 (10)	0.2154 (5)	0.064 (2)
H15	1.3101	1.1235	0.2064	0.077*
C16	1.1642 (8)	1.0554 (10)	0.1565 (5)	0.064 (2)
H16	1.1957	1.0316	0.1068	0.077*
C17	1.0504 (8)	1.0362 (11)	0.1704 (5)	0.073 (3)
H17	1.0030	0.9989	0.1296	0.088*
C18	1.0023 (7)	1.0698 (10)	0.2428 (4)	0.067 (3)
H18	0.9228	1.0583	0.2510	0.080*

	U11	U22	U33	U12	U13	U23
Hg1	0.0548 (2)	0.0531 (2)	0.0761 (3)	−0.00007 (16)	0.00288 (16)	−0.01027 (17)
Cl1	0.0604 (13)	0.0501 (12)	0.0617 (11)	−0.0058 (10)	0.0020 (9)	0.0005 (10)
Cl2	0.0529 (12)	0.0545 (13)	0.0818 (13)	0.0041 (10)	−0.0016 (10)	−0.0070 (11)
N1	0.049 (4)	0.046 (4)	0.062 (4)	0.002 (3)	0.008 (3)	0.000 (3)
N2	0.053 (4)	0.038 (4)	0.051 (3)	−0.001 (3)	−0.005 (3)	0.000 (3)
N3	0.063 (5)	0.069 (5)	0.058 (4)	−0.017 (4)	0.012 (3)	−0.017 (4)
C1	0.059 (6)	0.047 (5)	0.098 (6)	−0.002 (4)	0.012 (5)	−0.002 (5)
C2	0.059 (6)	0.062 (7)	0.076 (6)	0.002 (4)	0.021 (4)	−0.003 (5)
C3	0.064 (6)	0.064 (6)	0.068 (5)	0.010 (5)	0.024 (4)	−0.006 (5)
C4	0.064 (6)	0.059 (6)	0.068 (5)	0.000 (4)	0.004 (4)	−0.016 (5)
C5	0.043 (4)	0.046 (5)	0.054 (4)	0.004 (3)	0.006 (3)	−0.007 (4)
C6	0.064 (5)	0.045 (5)	0.062 (5)	−0.004 (4)	0.006 (4)	−0.011 (4)
C7	0.058 (5)	0.047 (5)	0.057 (4)	0.000 (4)	0.001 (4)	0.008 (4)
C8	0.070 (6)	0.050 (6)	0.062 (5)	−0.010 (4)	0.015 (4)	−0.013 (4)
C9	0.060 (6)	0.063 (7)	0.067 (5)	−0.015 (4)	0.012 (4)	−0.008 (4)
C10	0.044 (5)	0.065 (6)	0.052 (4)	−0.006 (4)	0.010 (4)	−0.008 (4)
C11	0.059 (5)	0.050 (5)	0.062 (5)	0.001 (4)	0.008 (4)	−0.012 (4)
C12	0.064 (5)	0.040 (5)	0.061 (5)	−0.004 (4)	0.006 (4)	−0.011 (4)
C13	0.057 (5)	0.046 (5)	0.060 (5)	−0.001 (4)	0.001 (4)	0.000 (4)
C14	0.046 (5)	0.055 (5)	0.066 (5)	−0.006 (4)	0.001 (4)	0.003 (4)
C15	0.061 (6)	0.059 (6)	0.073 (6)	0.008 (4)	0.014 (5)	−0.001 (5)
C16	0.080 (6)	0.054 (6)	0.058 (5)	−0.005 (5)	0.011 (4)	−0.002 (4)
C17	0.075 (6)	0.074 (7)	0.070 (5)	−0.017 (5)	−0.007 (5)	−0.006 (5)
C18	0.053 (5)	0.087 (8)	0.062 (5)	−0.011 (5)	−0.001 (4)	−0.009 (5)

Hg1—N1	2.310 (6)	C7—C12	1.388 (10)
Hg1—Cl2	2.407 (2)	C7—C8	1.418 (11)
Hg1—Cl1	2.4474 (19)	C8—C9	1.360 (10)
Hg1—N2	2.467 (6)	C8—H8	0.9500
N1—C5	1.325 (9)	C9—C10	1.396 (10)
N1—C1	1.327 (10)	C9—H9	0.9500
N2—C6	1.269 (9)	C10—C11	1.383 (11)
N2—C7	1.414 (9)	C11—C12	1.381 (10)
N3—C10	1.392 (10)	C11—H11	0.9500
N3—C13	1.401 (9)	C12—H12	0.9500
N3—H3N	0.87 (2)	C13—C14	1.379 (10)
C1—C2	1.387 (11)	C13—C18	1.394 (10)
C1—H1	0.9500	C14—C15	1.371 (10)
C2—C3	1.334 (11)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.360 (11)
C3—C4	1.380 (11)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.370 (11)
C4—C5	1.386 (10)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.392 (10)
C5—C6	1.491 (10)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
N1—Hg1—Cl2	126.16 (16)	N2—C7—C8	123.6 (7)
N1—Hg1—Cl1	111.91 (16)	C9—C8—C7	120.0 (8)
Cl2—Hg1—Cl1	120.57 (7)	C9—C8—H8	120.0
N1—Hg1—N2	70.9 (2)	C7—C8—H8	120.0
Cl2—Hg1—N2	101.23 (15)	C8—C9—C10	121.2 (8)
Cl1—Hg1—N2	108.84 (13)	C8—C9—H9	119.4
C5—N1—C1	118.7 (7)	C10—C9—H9	119.4
C5—N1—Hg1	116.5 (5)	C11—C10—N3	122.2 (7)
C1—N1—Hg1	124.8 (6)	C11—C10—C9	119.5 (8)
C6—N2—C7	123.5 (7)	N3—C10—C9	118.2 (8)
C6—N2—Hg1	112.8 (5)	C12—C11—C10	119.5 (7)
C7—N2—Hg1	122.9 (5)	C12—C11—H11	120.2
C10—N3—C13	129.0 (7)	C10—C11—H11	120.2
C10—N3—H3N	117 (5)	C11—C12—C7	121.6 (7)
C13—N3—H3N	114 (6)	C11—C12—H12	119.2
N1—C1—C2	122.2 (8)	C7—C12—H12	119.2
N1—C1—H1	118.9	C14—C13—C18	118.4 (7)
C2—C1—H1	118.9	C14—C13—N3	119.2 (7)
C3—C2—C1	119.7 (8)	C18—C13—N3	122.2 (7)
C3—C2—H2	120.1	C15—C14—C13	121.1 (7)
C1—C2—H2	120.1	C15—C14—H14	119.4
C2—C3—C4	118.5 (8)	C13—C14—H14	119.4
C2—C3—H3	120.8	C16—C15—C14	121.1 (8)
C4—C3—H3	120.8	C16—C15—H15	119.4
C3—C4—C5	119.7 (8)	C14—C15—H15	119.4
C3—C4—H4	120.2	C15—C16—C17	118.6 (8)
C5—C4—H4	120.2	C15—C16—H16	120.7
N1—C5—C4	121.1 (7)	C17—C16—H16	120.7
N1—C5—C6	119.3 (7)	C16—C17—C18	121.8 (8)
C4—C5—C6	119.5 (7)	C16—C17—H17	119.1
N2—C6—C5	119.9 (7)	C18—C17—H17	119.1
N2—C6—H6	120.0	C17—C18—C13	118.9 (8)
C5—C6—H6	120.0	C17—C18—H18	120.6
C12—C7—N2	118.2 (7)	C13—C18—H18	120.6
C12—C7—C8	118.2 (7)
C5—N1—C1—C2	−2.7 (12)	C7—C8—C9—C10	2.6 (13)
Hg1—N1—C1—C2	176.9 (6)	C13—N3—C10—C11	25.0 (14)
N1—C1—C2—C3	−0.1 (13)	C13—N3—C10—C9	−157.8 (8)
C1—C2—C3—C4	2.7 (13)	C8—C9—C10—C11	−2.2 (13)
C2—C3—C4—C5	−2.6 (12)	C8—C9—C10—N3	−179.5 (8)
C1—N1—C5—C4	2.7 (11)	N3—C10—C11—C12	178.2 (7)
Hg1—N1—C5—C4	−176.9 (5)	C9—C10—C11—C12	1.1 (12)
C1—N1—C5—C6	−177.4 (7)	C10—C11—C12—C7	−0.4 (12)
Hg1—N1—C5—C6	2.9 (8)	N2—C7—C12—C11	−178.9 (7)
C3—C4—C5—N1	−0.1 (11)	C8—C7—C12—C11	0.7 (11)
C3—C4—C5—C6	−180.0 (7)	C10—N3—C13—C14	−156.2 (9)
C7—N2—C6—C5	−177.1 (6)	C10—N3—C13—C18	28.2 (14)
Hg1—N2—C6—C5	−6.9 (8)	C18—C13—C14—C15	−3.6 (12)
N1—C5—C6—N2	3.1 (11)	N3—C13—C14—C15	−179.4 (8)
C4—C5—C6—N2	−177.1 (7)	C13—C14—C15—C16	1.8 (13)
C6—N2—C7—C12	−176.5 (7)	C14—C15—C16—C17	0.2 (13)
Hg1—N2—C7—C12	14.2 (9)	C15—C16—C17—C18	−0.2 (14)
C6—N2—C7—C8	4.0 (11)	C16—C17—C18—C13	−1.7 (14)
Hg1—N2—C7—C8	−165.3 (6)	C14—C13—C18—C17	3.5 (13)
C12—C7—C8—C9	−1.8 (12)	N3—C13—C18—C17	179.1 (8)
N2—C7—C8—C9	177.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···Cl2i	0.87 (2)	2.67 (3)	3.510 (7)	161 (7)
C1—H1···Cl1ii	0.95	2.74	3.493 (9)	136
C6—H6···Cl1iii	0.95	2.82	3.526 (9)	132

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3H3NCl2i	0.87(2)	2.67(3)	3.510(7)	161(7)
C1H1Cl1ii	0.95	2.74	3.493(9)	136
C6H6Cl1iii	0.95	2.82	3.526(9)	132

Symmetry codes: (i) ; (ii) ; (iii) .