metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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catena-Poly[[[di­chloridomercury(II)]-μ-1,4-bis­­(3-pyridyl­amino­meth­yl)benzene-κ2N:N′] N,N-di­methyl­formamide monosolvate]

aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 28 June 2011; accepted 1 July 2011; online 9 July 2011)

The crystal structure of the polymeric title compound, {[HgCl2(C18H18N4)]·C3H7NO}n, features an N-heterocyclic ligand which links adjacent HgCl2 units into a helical chain running along the b axis. The coordination geometry of the HgII atom is a distorted tetra­hedron. The dimethyl­formamide mol­ecule is disordered over two positions in a 1:1 ratio, and is linked to the complex mol­ecules via N—H⋯O hydrogen bonds.

Related literature

For the structure of the N-heterocyclic ligand, see: Zhu et al. (2007[Zhu, L.-N., Gao, S. & Huo, L.-H. (2007). Acta Cryst. E63, o4459.]).

[Scheme 1]

Experimental

Crystal data
  • [HgCl2(C18H18N4)]·C3H7NO

  • Mr = 634.95

  • Monoclinic, P 21 /n

  • a = 8.4851 (9) Å

  • b = 15.1215 (14) Å

  • c = 19.490 (2) Å

  • β = 103.826 (2)°

  • V = 2428.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.58 mm−1

  • T = 293 K

  • 0.15 × 0.11 × 0.11 mm

Data collection
  • Rigaku R-AXIS RAPID IP diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.439, Tmax = 0.531

  • 22980 measured reflections

  • 5479 independent reflections

  • 2593 reflections with I > 2σ(I)

  • Rint = 0.089

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.167

  • S = 1.05

  • 5479 reflections

  • 290 parameters

  • 42 restraints

  • H-atom parameters constrained

  • Δρmax = 1.26 e Å−3

  • Δρmin = −1.31 e Å−3

Table 1
Selected bond lengths (Å)

Hg1—N1 2.395 (7)
Hg1—N4i 2.308 (6)
Hg1—Cl1 2.355 (3)
Hg1—Cl2 2.391 (3)
Symmetry code: (i) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯O1 0.88 2.15 3.03 (3) 174
N2—H2N⋯O1′ 0.88 2.11 2.99 (3) 180
N3—H3N⋯O1ii 0.88 2.14 3.01 (3) 166
N3—H3N⋯O1′ii 0.88 2.13 2.98 (3) 162
Symmetry code: (ii) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

1,4-Bis(2-pyridylaminomethyl)benzene is a flexible N-heterocycle whose pyridyl and amino N-atoms are capable for forming coordination polymers (Zhu et al., 2007). The crystal structure of HgCl2(C18H18N4).DMF features the N-heterocycle linking adjacent HgCl2 units into a helical chain (Scheme I, Fig. 1). The geometry of HgII is a tetrahedron. The lattice DMF molecule is disordered in two positions in a 1:1 ratio. The N-heterocycle forms an N–H···O hydrogen bond to the solvent molecule at an N···O distance of 2.99 (3) and 3.03 (3) Å; the hydrogen bond probably stabilizes the solvent molecule so that it is not lost during crystallization.

Related literature top

For the structure of the N-heterocyclic ligand, see: Zhu et al. (2007).

Experimental top

A THF solution (10 ml) of mercuric chloride (2 mmol) was mixed with a DMF solution (5 ml) of 1,4-bis(3-pyridylaminomethyl)benzene (2 mmol). The solution was filtered and sent aside for the grown of colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atoms similar treated (N–H 0.86 Å).

The lattice DMF molecule is disordered over two sites; the disorder could not be refined, and was assumed to be a 1:1 type of disorder. The C–O distances were restrained to 1.25±0.01 Å, the Ccarbonyl–N distances to 1.35±0.01 Å and the N–Cmethyl distances to 1.45±0.01 Å. Each component was retrained to planar, with a maximum deviation of 0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones, and the anisotropic temperature factors were restrained to be nearly isotropic.

The final difference Fourier map had peaks/holes in the vicinity of Hg1.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the polymeric chain structure of HgCl2(C18H18N4).DMF at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary. radius.
catena-Poly[[[dichloridomercury(II)]-µ-1,4-bis(3- pyridylaminomethyl)benzene-κ2N:N'] N,N-dimethylformamide monosolvate] top
Crystal data top
[HgCl2(C18H18N4)]·C3H7NOF(000) = 1232
Mr = 634.95Dx = 1.737 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 10259 reflections
a = 8.4851 (9) Åθ = 3.2–27.5°
b = 15.1215 (14) ŵ = 6.58 mm1
c = 19.490 (2) ÅT = 293 K
β = 103.826 (2)°Prism, colorless
V = 2428.2 (4) Å30.15 × 0.11 × 0.11 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
5479 independent reflections
Radiation source: fine-focus sealed tube2593 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.089
ω scanθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.439, Tmax = 0.531k = 1919
22980 measured reflectionsl = 2522
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0656P)2]
where P = (Fo2 + 2Fc2)/3
5479 reflections(Δ/σ)max = 0.001
290 parametersΔρmax = 1.26 e Å3
42 restraintsΔρmin = 1.31 e Å3
Crystal data top
[HgCl2(C18H18N4)]·C3H7NOV = 2428.2 (4) Å3
Mr = 634.95Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.4851 (9) ŵ = 6.58 mm1
b = 15.1215 (14) ÅT = 293 K
c = 19.490 (2) Å0.15 × 0.11 × 0.11 mm
β = 103.826 (2)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
5479 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2593 reflections with I > 2σ(I)
Tmin = 0.439, Tmax = 0.531Rint = 0.089
22980 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05142 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.05Δρmax = 1.26 e Å3
5479 reflectionsΔρmin = 1.31 e Å3
290 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Hg10.65054 (5)0.63785 (2)0.73300 (2)0.0944 (2)
Cl10.3880 (4)0.5916 (3)0.7371 (2)0.1488 (12)
Cl20.7868 (4)0.77413 (15)0.72364 (19)0.1366 (11)
N10.7052 (9)0.5581 (4)0.6351 (4)0.0845 (19)
N20.5616 (9)0.3645 (4)0.5347 (5)0.097 (2)
H2N0.49120.34820.55890.116*
N31.2859 (9)0.1242 (4)0.5624 (4)0.089 (2)
H3N1.28880.18190.56850.106*
N41.6587 (8)0.0700 (4)0.6783 (3)0.0778 (18)
C10.6262 (10)0.4841 (5)0.6124 (5)0.077 (2)
H10.55280.46190.63660.092*
C20.6491 (10)0.4383 (5)0.5535 (5)0.078 (2)
C30.7569 (11)0.4741 (7)0.5156 (5)0.097 (3)
H30.77200.44570.47530.117*
C40.8377 (13)0.5496 (7)0.5381 (6)0.105 (3)
H40.91080.57340.51440.126*
C50.8089 (11)0.5909 (6)0.5976 (6)0.098 (3)
H50.86310.64350.61270.118*
C60.5810 (12)0.3099 (7)0.4743 (5)0.108 (3)
H6A0.57690.34850.43420.130*
H6B0.48940.26980.46170.130*
C70.7345 (10)0.2565 (5)0.4868 (5)0.077 (2)
C80.7897 (12)0.2164 (6)0.5502 (6)0.100 (3)
H80.73790.22570.58660.120*
C90.9204 (13)0.1631 (7)0.5601 (5)0.101 (3)
H90.95590.13490.60350.121*
C101.0050 (10)0.1482 (5)0.5074 (5)0.073 (2)
C110.9536 (11)0.1896 (6)0.4447 (5)0.085 (2)
H111.00700.18110.40870.102*
C120.8207 (12)0.2447 (6)0.4349 (5)0.093 (3)
H120.78750.27490.39230.111*
C131.1469 (10)0.0856 (6)0.5190 (6)0.098 (3)
H13A1.12040.03170.54080.118*
H13B1.16850.07010.47380.118*
C141.5277 (9)0.1115 (5)0.6468 (4)0.0675 (19)
H141.51190.16880.66100.081*
C151.4147 (9)0.0755 (5)0.5950 (4)0.0700 (19)
C161.4362 (11)0.0123 (5)0.5778 (5)0.083 (2)
H161.35880.04060.54290.100*
C171.5701 (12)0.0560 (6)0.6123 (5)0.092 (3)
H171.58350.11520.60200.111*
C181.6827 (11)0.0152 (5)0.6607 (5)0.083 (2)
H181.77780.04460.68250.100*
O10.300 (4)0.314 (2)0.6094 (14)0.110 (3)0.50
N50.181 (3)0.3560 (13)0.7007 (11)0.085 (3)0.50
C190.303 (3)0.3275 (14)0.6732 (14)0.128 (6)0.50
H190.40110.31630.70530.154*0.50
C200.025 (3)0.375 (2)0.6545 (18)0.197 (11)0.50
H20A0.03330.42620.62670.295*0.50
H20B0.05250.38560.68230.295*0.50
H20C0.00960.32520.62390.295*0.50
C210.180 (5)0.380 (2)0.7725 (13)0.185 (9)0.50
H21A0.12300.43490.77230.278*0.50
H21B0.28990.38680.79980.278*0.50
H21C0.12730.33460.79310.278*0.50
O1'0.323 (4)0.309 (2)0.6172 (14)0.110 (3)0.50
N5'0.181 (3)0.3701 (11)0.6889 (12)0.085 (3)0.50
C19'0.200 (3)0.3494 (13)0.6242 (13)0.128 (6)0.50
H19'0.12030.36540.58440.154*0.50
C20'0.052 (4)0.416 (2)0.712 (2)0.197 (11)0.50
H20D0.03390.37510.71280.295*0.50
H20E0.01130.46290.67930.295*0.50
H20F0.09400.43980.75800.295*0.50
C21'0.308 (3)0.344 (2)0.7492 (15)0.185 (9)0.50
H21D0.33510.28280.74430.278*0.50
H21E0.27040.35090.79170.278*0.50
H21F0.40200.37980.75170.278*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.0921 (3)0.0868 (3)0.0909 (3)0.00588 (18)0.0045 (2)0.00621 (18)
Cl10.096 (2)0.202 (3)0.142 (3)0.024 (2)0.017 (2)0.030 (3)
Cl20.139 (3)0.0719 (13)0.172 (3)0.0028 (14)0.015 (2)0.0193 (16)
N10.071 (5)0.083 (4)0.092 (5)0.005 (4)0.007 (4)0.001 (4)
N20.065 (5)0.099 (5)0.123 (7)0.002 (4)0.014 (5)0.031 (5)
N30.066 (5)0.072 (4)0.116 (6)0.005 (3)0.003 (4)0.016 (4)
N40.079 (5)0.073 (4)0.065 (4)0.009 (3)0.014 (3)0.005 (3)
C10.062 (5)0.080 (5)0.081 (5)0.007 (4)0.002 (4)0.002 (4)
C20.062 (5)0.078 (5)0.089 (6)0.013 (4)0.010 (5)0.010 (5)
C30.078 (7)0.114 (8)0.097 (7)0.020 (5)0.014 (6)0.012 (6)
C40.107 (8)0.103 (7)0.113 (8)0.004 (6)0.041 (7)0.005 (6)
C50.072 (6)0.086 (6)0.126 (8)0.002 (5)0.004 (6)0.003 (6)
C60.096 (7)0.108 (7)0.101 (7)0.026 (6)0.016 (6)0.034 (6)
C70.064 (5)0.081 (5)0.082 (6)0.013 (4)0.005 (5)0.010 (4)
C80.092 (7)0.113 (7)0.101 (7)0.036 (6)0.037 (6)0.020 (6)
C90.113 (8)0.122 (7)0.066 (6)0.029 (6)0.017 (6)0.021 (5)
C100.057 (5)0.070 (4)0.080 (6)0.007 (4)0.006 (4)0.007 (4)
C110.083 (6)0.100 (6)0.075 (6)0.016 (5)0.023 (5)0.007 (5)
C120.104 (8)0.107 (6)0.063 (5)0.025 (5)0.012 (5)0.002 (5)
C130.066 (6)0.090 (6)0.119 (8)0.007 (5)0.017 (5)0.029 (5)
C140.058 (5)0.068 (4)0.056 (4)0.010 (3)0.027 (3)0.004 (3)
C150.063 (5)0.069 (4)0.068 (5)0.012 (4)0.004 (4)0.003 (4)
C160.086 (6)0.067 (4)0.083 (6)0.007 (4)0.006 (5)0.011 (4)
C170.094 (7)0.070 (5)0.099 (7)0.009 (5)0.006 (6)0.006 (5)
C180.082 (6)0.070 (5)0.083 (6)0.007 (4)0.009 (5)0.003 (4)
O10.108 (7)0.101 (4)0.125 (6)0.006 (5)0.035 (5)0.011 (4)
N50.083 (5)0.087 (6)0.082 (6)0.010 (4)0.015 (5)0.016 (5)
C190.125 (10)0.134 (9)0.122 (10)0.015 (7)0.023 (8)0.009 (8)
C200.188 (13)0.210 (14)0.193 (14)0.023 (9)0.047 (10)0.009 (9)
C210.189 (12)0.195 (12)0.177 (12)0.005 (9)0.054 (9)0.000 (9)
O1'0.108 (7)0.101 (4)0.125 (6)0.006 (5)0.035 (5)0.011 (4)
N5'0.083 (5)0.087 (6)0.082 (6)0.010 (4)0.015 (5)0.016 (5)
C19'0.125 (10)0.134 (9)0.122 (10)0.015 (7)0.023 (8)0.009 (8)
C20'0.188 (13)0.210 (14)0.193 (14)0.023 (9)0.047 (10)0.009 (9)
C21'0.189 (12)0.195 (12)0.177 (12)0.005 (9)0.054 (9)0.000 (9)
Geometric parameters (Å, º) top
Hg1—N12.395 (7)C11—H110.9300
Hg1—N4i2.308 (6)C12—H120.9300
Hg1—Cl12.355 (3)C13—H13A0.9700
Hg1—Cl22.391 (3)C13—H13B0.9700
N1—C11.325 (10)C14—C151.331 (10)
N1—C51.364 (11)C14—H140.9300
N2—C21.342 (10)C15—C161.392 (10)
N2—C61.479 (11)C16—C171.346 (12)
N2—H2N0.8800C16—H160.9300
N3—C151.345 (10)C17—C181.324 (11)
N3—C131.404 (10)C17—H170.9300
N3—H3N0.8800C18—H180.9300
N4—C141.296 (9)O1—C191.253 (10)
N4—C181.361 (9)N5—C191.344 (10)
N4—Hg1ii2.308 (6)N5—C201.440 (10)
C1—C21.392 (11)N5—C211.448 (10)
C1—H10.9300C19—H190.9300
C2—C31.414 (12)C20—H20A0.9600
C3—C41.351 (13)C20—H20B0.9600
C3—H30.9300C20—H20C0.9600
C4—C51.390 (13)C21—H21A0.9600
C4—H40.9300C21—H21B0.9600
C5—H50.9300C21—H21C0.9600
C6—C71.502 (11)O1'—C19'1.250 (10)
C6—H6A0.9700N5'—C19'1.346 (10)
C6—H6B0.9700N5'—C20'1.448 (10)
C7—C81.356 (12)N5'—C21'1.449 (10)
C7—C121.394 (11)C19'—H19'0.9300
C8—C91.347 (12)C20'—H20D0.9600
C8—H80.9300C20'—H20E0.9600
C9—C101.405 (12)C20'—H20F0.9600
C9—H90.9300C21'—H21D0.9600
C10—C111.348 (11)C21'—H21E0.9600
C10—C131.506 (11)C21'—H21F0.9600
C11—C121.378 (11)
N4i—Hg1—Cl1110.0 (2)C10—C11—C12118.9 (8)
N4i—Hg1—Cl2100.07 (18)C10—C11—H11120.6
Cl1—Hg1—Cl2137.49 (12)C12—C11—H11120.6
N4i—Hg1—N197.9 (2)C11—C12—C7122.1 (8)
Cl1—Hg1—N1104.0 (2)C11—C12—H12119.0
Cl2—Hg1—N1100.6 (2)C7—C12—H12119.0
C1—N1—C5117.9 (8)N3—C13—C10110.8 (7)
C1—N1—Hg1120.9 (6)N3—C13—H13A109.5
C5—N1—Hg1121.1 (6)C10—C13—H13A109.5
C2—N2—C6121.5 (8)N3—C13—H13B109.5
C2—N2—H2N119.2C10—C13—H13B109.5
C6—N2—H2N119.2H13A—C13—H13B108.1
C15—N3—C13121.9 (7)N4—C14—C15122.8 (7)
C15—N3—H3N119.0N4—C14—H14118.6
C13—N3—H3N119.0C15—C14—H14118.6
C14—N4—C18120.1 (7)C14—C15—N3119.4 (7)
C14—N4—Hg1ii120.6 (5)C14—C15—C16117.4 (7)
C18—N4—Hg1ii119.3 (5)N3—C15—C16123.2 (8)
N1—C1—C2122.4 (8)C17—C16—C15119.4 (8)
N1—C1—H1118.8C17—C16—H16120.3
C2—C1—H1118.8C15—C16—H16120.3
N2—C2—C1117.5 (8)C18—C17—C16120.4 (8)
N2—C2—C3124.0 (8)C18—C17—H17119.8
C1—C2—C3118.4 (8)C16—C17—H17119.8
C4—C3—C2119.7 (9)C17—C18—N4119.7 (8)
C4—C3—H3120.1C17—C18—H18120.2
C2—C3—H3120.1N4—C18—H18120.2
C3—C4—C5118.3 (9)C19—N5—C20120 (3)
C3—C4—H4120.9C19—N5—C21130 (3)
C5—C4—H4120.9C20—N5—C21110 (3)
N1—C5—C4123.3 (9)O1—C19—N5128 (3)
N1—C5—H5118.4O1—C19—H19116.2
C4—C5—H5118.4N5—C19—H19116.2
N2—C6—C7115.3 (8)C19'—N5'—C20'132 (3)
N2—C6—H6A108.4C19'—N5'—C21'118 (2)
C7—C6—H6A108.4C20'—N5'—C21'111 (2)
N2—C6—H6B108.4O1'—C19'—N5'121 (3)
C7—C6—H6B108.4O1'—C19'—H19'119.7
H6A—C6—H6B107.5N5'—C19'—H19'119.7
C8—C7—C12118.5 (8)N5'—C20'—H20D109.5
C8—C7—C6119.1 (8)N5'—C20'—H20E109.5
C12—C7—C6122.4 (9)H20D—C20'—H20E109.5
C9—C8—C7119.4 (8)N5'—C20'—H20F109.5
C9—C8—H8120.3H20D—C20'—H20F109.5
C7—C8—H8120.3H20E—C20'—H20F109.5
C8—C9—C10122.6 (9)N5'—C21'—H21D109.5
C8—C9—H9118.7N5'—C21'—H21E109.5
C10—C9—H9118.7H21D—C21'—H21E109.5
C11—C10—C9118.5 (7)N5'—C21'—H21F109.5
C11—C10—C13120.1 (8)H21D—C21'—H21F109.5
C9—C10—C13121.4 (8)H21E—C21'—H21F109.5
N4i—Hg1—N1—C190.8 (6)C8—C9—C10—C13177.7 (10)
Cl1—Hg1—N1—C122.2 (7)C9—C10—C11—C120.1 (13)
Cl2—Hg1—N1—C1167.3 (6)C13—C10—C11—C12178.2 (8)
N4i—Hg1—N1—C594.4 (7)C10—C11—C12—C72.3 (15)
Cl1—Hg1—N1—C5152.6 (6)C8—C7—C12—C114.0 (15)
Cl2—Hg1—N1—C57.5 (7)C6—C7—C12—C11174.4 (9)
C5—N1—C1—C21.8 (12)C15—N3—C13—C10162.7 (8)
Hg1—N1—C1—C2176.8 (6)C11—C10—C13—N3105.7 (10)
C6—N2—C2—C1178.2 (7)C9—C10—C13—N376.3 (12)
C6—N2—C2—C34.8 (14)C18—N4—C14—C152.5 (12)
N1—C1—C2—N2179.4 (8)Hg1ii—N4—C14—C15179.4 (6)
N1—C1—C2—C32.1 (13)N4—C14—C15—N3176.6 (8)
N2—C2—C3—C4178.9 (9)N4—C14—C15—C164.0 (12)
C1—C2—C3—C41.8 (14)C13—N3—C15—C14165.7 (8)
C2—C3—C4—C51.4 (15)C13—N3—C15—C1613.6 (14)
C1—N1—C5—C41.3 (14)C14—C15—C16—C171.8 (13)
Hg1—N1—C5—C4176.3 (7)N3—C15—C16—C17178.9 (9)
C3—C4—C5—N11.1 (16)C15—C16—C17—C181.9 (15)
C2—N2—C6—C773.2 (12)C16—C17—C18—N43.5 (14)
N2—C6—C7—C840.2 (13)C14—N4—C18—C171.4 (12)
N2—C6—C7—C12141.5 (9)Hg1ii—N4—C18—C17176.7 (7)
C12—C7—C8—C93.4 (15)C20—N5—C19—O10.0 (2)
C6—C7—C8—C9175.0 (10)C21—N5—C19—O1174 (3)
C7—C8—C9—C101.3 (17)C20'—N5'—C19'—O1'180.0 (4)
C8—C9—C10—C110.4 (15)C21'—N5'—C19'—O1'0.0 (3)
Symmetry codes: (i) x+5/2, y+1/2, z+3/2; (ii) x+5/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.882.153.03 (3)174
N2—H2N···O10.882.112.99 (3)180
N3—H3N···O1iii0.882.143.01 (3)166
N3—H3N···O1iii0.882.132.98 (3)162
Symmetry code: (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[HgCl2(C18H18N4)]·C3H7NO
Mr634.95
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.4851 (9), 15.1215 (14), 19.490 (2)
β (°) 103.826 (2)
V3)2428.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)6.58
Crystal size (mm)0.15 × 0.11 × 0.11
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.439, 0.531
No. of measured, independent and
observed [I > 2σ(I)] reflections
22980, 5479, 2593
Rint0.089
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.167, 1.05
No. of reflections5479
No. of parameters290
No. of restraints42
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.26, 1.31

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Hg1—N12.395 (7)Hg1—Cl12.355 (3)
Hg1—N4i2.308 (6)Hg1—Cl22.391 (3)
Symmetry code: (i) x+5/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.882.153.03 (3)174
N2—H2N···O1'0.882.112.99 (3)180
N3—H3N···O1ii0.882.143.01 (3)166
N3—H3N···O1'ii0.882.132.98 (3)162
Symmetry code: (ii) x+1, y, z.
 

Acknowledgements

This work is supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), the Key Project of the Education Bureau of Heilongjiang Province, China (No. 12511z023) and the University of Malaya.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhu, L.-N., Gao, S. & Huo, L.-H. (2007). Acta Cryst. E63, o4459.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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