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

Gao, S.; Ng, S.W.

doi:10.1107/S1600536811026043

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1051

doi:10.1107/S1600536811026043

Open

access

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

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^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 Hg^II 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 ).

Experimental

Crystal data

[HgCl₂(C₁₈H₁₈N₄)]·C₃H₇NO
M_r = 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 ) T_min = 0.439, T_max = 0.531
22980 measured reflections
5479 independent reflections
2593 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 1.26 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: RAPID-AUTO; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026043/xu5257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026043/xu5257Isup2.hkl

checkCIF report

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 Hg^II 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.

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

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)]·C₃H₇NO	F(000) = 1232
M_r = 634.95	D_x = 1.737 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10259 reflections
a = 8.4851 (9) Å	θ = 3.2–27.5°
b = 15.1215 (14) Å	µ = 6.58 mm⁻¹
c = 19.490 (2) Å	T = 293 K
β = 103.826 (2)°	Prism, colorless
V = 2428.2 (4) Å³	0.15 × 0.11 × 0.11 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5479 independent reflections
Radiation source: fine-focus sealed tube	2593 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
ω scan	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
T_min = 0.439, T_max = 0.531	k = −19→19
22980 measured reflections	l = −25→22

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0656P)²] where P = (F_o² + 2F_c²)/3
5479 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 1.26 e Å⁻³
42 restraints	Δρ_min = −1.31 e Å⁻³

Crystal data top

[HgCl₂(C₁₈H₁₈N₄)]·C₃H₇NO	V = 2428.2 (4) Å³
M_r = 634.95	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4851 (9) Å	µ = 6.58 mm⁻¹
b = 15.1215 (14) Å	T = 293 K
c = 19.490 (2) Å	0.15 × 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)
T_min = 0.439, T_max = 0.531	R_int = 0.089
22980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	42 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.05	Δρ_max = 1.26 e Å⁻³
5479 reflections	Δρ_min = −1.31 e Å⁻³
290 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Hg1	0.65054 (5)	0.63785 (2)	0.73300 (2)	0.0944 (2)
Cl1	0.3880 (4)	0.5916 (3)	0.7371 (2)	0.1488 (12)
Cl2	0.7868 (4)	0.77413 (15)	0.72364 (19)	0.1366 (11)
N1	0.7052 (9)	0.5581 (4)	0.6351 (4)	0.0845 (19)
N2	0.5616 (9)	0.3645 (4)	0.5347 (5)	0.097 (2)
H2N	0.4912	0.3482	0.5589	0.116*
N3	1.2859 (9)	0.1242 (4)	0.5624 (4)	0.089 (2)
H3N	1.2888	0.1819	0.5685	0.106*
N4	1.6587 (8)	0.0700 (4)	0.6783 (3)	0.0778 (18)
C1	0.6262 (10)	0.4841 (5)	0.6124 (5)	0.077 (2)
H1	0.5528	0.4619	0.6366	0.092*
C2	0.6491 (10)	0.4383 (5)	0.5535 (5)	0.078 (2)
C3	0.7569 (11)	0.4741 (7)	0.5156 (5)	0.097 (3)
H3	0.7720	0.4457	0.4753	0.117*
C4	0.8377 (13)	0.5496 (7)	0.5381 (6)	0.105 (3)
H4	0.9108	0.5734	0.5144	0.126*
C5	0.8089 (11)	0.5909 (6)	0.5976 (6)	0.098 (3)
H5	0.8631	0.6435	0.6127	0.118*
C6	0.5810 (12)	0.3099 (7)	0.4743 (5)	0.108 (3)
H6A	0.5769	0.3485	0.4342	0.130*
H6B	0.4894	0.2698	0.4617	0.130*
C7	0.7345 (10)	0.2565 (5)	0.4868 (5)	0.077 (2)
C8	0.7897 (12)	0.2164 (6)	0.5502 (6)	0.100 (3)
H8	0.7379	0.2257	0.5866	0.120*
C9	0.9204 (13)	0.1631 (7)	0.5601 (5)	0.101 (3)
H9	0.9559	0.1349	0.6035	0.121*
C10	1.0050 (10)	0.1482 (5)	0.5074 (5)	0.073 (2)
C11	0.9536 (11)	0.1896 (6)	0.4447 (5)	0.085 (2)
H11	1.0070	0.1811	0.4087	0.102*
C12	0.8207 (12)	0.2447 (6)	0.4349 (5)	0.093 (3)
H12	0.7875	0.2749	0.3923	0.111*
C13	1.1469 (10)	0.0856 (6)	0.5190 (6)	0.098 (3)
H13A	1.1204	0.0317	0.5408	0.118*
H13B	1.1685	0.0701	0.4738	0.118*
C14	1.5277 (9)	0.1115 (5)	0.6468 (4)	0.0675 (19)
H14	1.5119	0.1688	0.6610	0.081*
C15	1.4147 (9)	0.0755 (5)	0.5950 (4)	0.0700 (19)
C16	1.4362 (11)	−0.0123 (5)	0.5778 (5)	0.083 (2)
H16	1.3588	−0.0406	0.5429	0.100*
C17	1.5701 (12)	−0.0560 (6)	0.6123 (5)	0.092 (3)
H17	1.5835	−0.1152	0.6020	0.111*
C18	1.6827 (11)	−0.0152 (5)	0.6607 (5)	0.083 (2)
H18	1.7778	−0.0446	0.6825	0.100*
O1	0.300 (4)	0.314 (2)	0.6094 (14)	0.110 (3)	0.50
N5	0.181 (3)	0.3560 (13)	0.7007 (11)	0.085 (3)	0.50
C19	0.303 (3)	0.3275 (14)	0.6732 (14)	0.128 (6)	0.50
H19	0.4011	0.3163	0.7053	0.154*	0.50
C20	0.025 (3)	0.375 (2)	0.6545 (18)	0.197 (11)	0.50
H20A	0.0333	0.4262	0.6267	0.295*	0.50
H20B	−0.0525	0.3856	0.6823	0.295*	0.50
H20C	−0.0096	0.3252	0.6239	0.295*	0.50
C21	0.180 (5)	0.380 (2)	0.7725 (13)	0.185 (9)	0.50
H21A	0.1230	0.4349	0.7723	0.278*	0.50
H21B	0.2899	0.3868	0.7998	0.278*	0.50
H21C	0.1273	0.3346	0.7931	0.278*	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'	0.1203	0.3654	0.5844	0.154*	0.50
C20'	0.052 (4)	0.416 (2)	0.712 (2)	0.197 (11)	0.50
H20D	−0.0339	0.3751	0.7128	0.295*	0.50
H20E	0.0113	0.4629	0.6793	0.295*	0.50
H20F	0.0940	0.4398	0.7580	0.295*	0.50
C21'	0.308 (3)	0.344 (2)	0.7492 (15)	0.185 (9)	0.50
H21D	0.3351	0.2828	0.7443	0.278*	0.50
H21E	0.2704	0.3509	0.7917	0.278*	0.50
H21F	0.4020	0.3798	0.7517	0.278*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0921 (3)	0.0868 (3)	0.0909 (3)	0.00588 (18)	−0.0045 (2)	−0.00621 (18)
Cl1	0.096 (2)	0.202 (3)	0.142 (3)	−0.024 (2)	0.017 (2)	−0.030 (3)
Cl2	0.139 (3)	0.0719 (13)	0.172 (3)	0.0028 (14)	−0.015 (2)	0.0193 (16)
N1	0.071 (5)	0.083 (4)	0.092 (5)	0.005 (4)	0.007 (4)	−0.001 (4)
N2	0.065 (5)	0.099 (5)	0.123 (7)	0.002 (4)	0.014 (5)	−0.031 (5)
N3	0.066 (5)	0.072 (4)	0.116 (6)	0.005 (3)	−0.003 (4)	−0.016 (4)
N4	0.079 (5)	0.073 (4)	0.065 (4)	−0.009 (3)	−0.014 (3)	−0.005 (3)
C1	0.062 (5)	0.080 (5)	0.081 (5)	0.007 (4)	0.002 (4)	0.002 (4)
C2	0.062 (5)	0.078 (5)	0.089 (6)	0.013 (4)	0.010 (5)	−0.010 (5)
C3	0.078 (7)	0.114 (8)	0.097 (7)	0.020 (5)	0.014 (6)	−0.012 (6)
C4	0.107 (8)	0.103 (7)	0.113 (8)	0.004 (6)	0.041 (7)	0.005 (6)
C5	0.072 (6)	0.086 (6)	0.126 (8)	−0.002 (5)	0.004 (6)	0.003 (6)
C6	0.096 (7)	0.108 (7)	0.101 (7)	0.026 (6)	−0.016 (6)	−0.034 (6)
C7	0.064 (5)	0.081 (5)	0.082 (6)	0.013 (4)	0.005 (5)	−0.010 (4)
C8	0.092 (7)	0.113 (7)	0.101 (7)	0.036 (6)	0.037 (6)	0.020 (6)
C9	0.113 (8)	0.122 (7)	0.066 (6)	0.029 (6)	0.017 (6)	0.021 (5)
C10	0.057 (5)	0.070 (4)	0.080 (6)	0.007 (4)	−0.006 (4)	−0.007 (4)
C11	0.083 (6)	0.100 (6)	0.075 (6)	0.016 (5)	0.023 (5)	−0.007 (5)
C12	0.104 (8)	0.107 (6)	0.063 (5)	0.025 (5)	0.012 (5)	−0.002 (5)
C13	0.066 (6)	0.090 (6)	0.119 (8)	0.007 (5)	−0.017 (5)	−0.029 (5)
C14	0.058 (5)	0.068 (4)	0.056 (4)	0.010 (3)	−0.027 (3)	−0.004 (3)
C15	0.063 (5)	0.069 (4)	0.068 (5)	0.012 (4)	−0.004 (4)	0.003 (4)
C16	0.086 (6)	0.067 (4)	0.083 (6)	0.007 (4)	−0.006 (5)	−0.011 (4)
C17	0.094 (7)	0.070 (5)	0.099 (7)	0.009 (5)	−0.006 (6)	−0.006 (5)
C18	0.082 (6)	0.070 (5)	0.083 (6)	0.007 (4)	−0.009 (5)	−0.003 (4)
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)
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—N1	2.395 (7)	C11—H11	0.9300
Hg1—N4ⁱ	2.308 (6)	C12—H12	0.9300
Hg1—Cl1	2.355 (3)	C13—H13A	0.9700
Hg1—Cl2	2.391 (3)	C13—H13B	0.9700
N1—C1	1.325 (10)	C14—C15	1.331 (10)
N1—C5	1.364 (11)	C14—H14	0.9300
N2—C2	1.342 (10)	C15—C16	1.392 (10)
N2—C6	1.479 (11)	C16—C17	1.346 (12)
N2—H2N	0.8800	C16—H16	0.9300
N3—C15	1.345 (10)	C17—C18	1.324 (11)
N3—C13	1.404 (10)	C17—H17	0.9300
N3—H3N	0.8800	C18—H18	0.9300
N4—C14	1.296 (9)	O1—C19	1.253 (10)
N4—C18	1.361 (9)	N5—C19	1.344 (10)
N4—Hg1ⁱⁱ	2.308 (6)	N5—C20	1.440 (10)
C1—C2	1.392 (11)	N5—C21	1.448 (10)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.414 (12)	C20—H20A	0.9600
C3—C4	1.351 (13)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.390 (13)	C21—H21A	0.9600
C4—H4	0.9300	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.502 (11)	O1'—C19'	1.250 (10)
C6—H6A	0.9700	N5'—C19'	1.346 (10)
C6—H6B	0.9700	N5'—C20'	1.448 (10)
C7—C8	1.356 (12)	N5'—C21'	1.449 (10)
C7—C12	1.394 (11)	C19'—H19'	0.9300
C8—C9	1.347 (12)	C20'—H20D	0.9600
C8—H8	0.9300	C20'—H20E	0.9600
C9—C10	1.405 (12)	C20'—H20F	0.9600
C9—H9	0.9300	C21'—H21D	0.9600
C10—C11	1.348 (11)	C21'—H21E	0.9600
C10—C13	1.506 (11)	C21'—H21F	0.9600
C11—C12	1.378 (11)

N4ⁱ—Hg1—Cl1	110.0 (2)	C10—C11—C12	118.9 (8)
N4ⁱ—Hg1—Cl2	100.07 (18)	C10—C11—H11	120.6
Cl1—Hg1—Cl2	137.49 (12)	C12—C11—H11	120.6
N4ⁱ—Hg1—N1	97.9 (2)	C11—C12—C7	122.1 (8)
Cl1—Hg1—N1	104.0 (2)	C11—C12—H12	119.0
Cl2—Hg1—N1	100.6 (2)	C7—C12—H12	119.0
C1—N1—C5	117.9 (8)	N3—C13—C10	110.8 (7)
C1—N1—Hg1	120.9 (6)	N3—C13—H13A	109.5
C5—N1—Hg1	121.1 (6)	C10—C13—H13A	109.5
C2—N2—C6	121.5 (8)	N3—C13—H13B	109.5
C2—N2—H2N	119.2	C10—C13—H13B	109.5
C6—N2—H2N	119.2	H13A—C13—H13B	108.1
C15—N3—C13	121.9 (7)	N4—C14—C15	122.8 (7)
C15—N3—H3N	119.0	N4—C14—H14	118.6
C13—N3—H3N	119.0	C15—C14—H14	118.6
C14—N4—C18	120.1 (7)	C14—C15—N3	119.4 (7)
C14—N4—Hg1ⁱⁱ	120.6 (5)	C14—C15—C16	117.4 (7)
C18—N4—Hg1ⁱⁱ	119.3 (5)	N3—C15—C16	123.2 (8)
N1—C1—C2	122.4 (8)	C17—C16—C15	119.4 (8)
N1—C1—H1	118.8	C17—C16—H16	120.3
C2—C1—H1	118.8	C15—C16—H16	120.3
N2—C2—C1	117.5 (8)	C18—C17—C16	120.4 (8)
N2—C2—C3	124.0 (8)	C18—C17—H17	119.8
C1—C2—C3	118.4 (8)	C16—C17—H17	119.8
C4—C3—C2	119.7 (9)	C17—C18—N4	119.7 (8)
C4—C3—H3	120.1	C17—C18—H18	120.2
C2—C3—H3	120.1	N4—C18—H18	120.2
C3—C4—C5	118.3 (9)	C19—N5—C20	120 (3)
C3—C4—H4	120.9	C19—N5—C21	130 (3)
C5—C4—H4	120.9	C20—N5—C21	110 (3)
N1—C5—C4	123.3 (9)	O1—C19—N5	128 (3)
N1—C5—H5	118.4	O1—C19—H19	116.2
C4—C5—H5	118.4	N5—C19—H19	116.2
N2—C6—C7	115.3 (8)	C19'—N5'—C20'	132 (3)
N2—C6—H6A	108.4	C19'—N5'—C21'	118 (2)
C7—C6—H6A	108.4	C20'—N5'—C21'	111 (2)
N2—C6—H6B	108.4	O1'—C19'—N5'	121 (3)
C7—C6—H6B	108.4	O1'—C19'—H19'	119.7
H6A—C6—H6B	107.5	N5'—C19'—H19'	119.7
C8—C7—C12	118.5 (8)	N5'—C20'—H20D	109.5
C8—C7—C6	119.1 (8)	N5'—C20'—H20E	109.5
C12—C7—C6	122.4 (9)	H20D—C20'—H20E	109.5
C9—C8—C7	119.4 (8)	N5'—C20'—H20F	109.5
C9—C8—H8	120.3	H20D—C20'—H20F	109.5
C7—C8—H8	120.3	H20E—C20'—H20F	109.5
C8—C9—C10	122.6 (9)	N5'—C21'—H21D	109.5
C8—C9—H9	118.7	N5'—C21'—H21E	109.5
C10—C9—H9	118.7	H21D—C21'—H21E	109.5
C11—C10—C9	118.5 (7)	N5'—C21'—H21F	109.5
C11—C10—C13	120.1 (8)	H21D—C21'—H21F	109.5
C9—C10—C13	121.4 (8)	H21E—C21'—H21F	109.5

N4ⁱ—Hg1—N1—C1	90.8 (6)	C8—C9—C10—C13	−177.7 (10)
Cl1—Hg1—N1—C1	−22.2 (7)	C9—C10—C11—C12	0.1 (13)
Cl2—Hg1—N1—C1	−167.3 (6)	C13—C10—C11—C12	178.2 (8)
N4ⁱ—Hg1—N1—C5	−94.4 (7)	C10—C11—C12—C7	−2.3 (15)
Cl1—Hg1—N1—C5	152.6 (6)	C8—C7—C12—C11	4.0 (15)
Cl2—Hg1—N1—C5	7.5 (7)	C6—C7—C12—C11	−174.4 (9)
C5—N1—C1—C2	1.8 (12)	C15—N3—C13—C10	162.7 (8)
Hg1—N1—C1—C2	176.8 (6)	C11—C10—C13—N3	105.7 (10)
C6—N2—C2—C1	−178.2 (7)	C9—C10—C13—N3	−76.3 (12)
C6—N2—C2—C3	4.8 (14)	C18—N4—C14—C15	−2.5 (12)
N1—C1—C2—N2	−179.4 (8)	Hg1ⁱⁱ—N4—C14—C15	179.4 (6)
N1—C1—C2—C3	−2.1 (13)	N4—C14—C15—N3	−176.6 (8)
N2—C2—C3—C4	178.9 (9)	N4—C14—C15—C16	4.0 (12)
C1—C2—C3—C4	1.8 (14)	C13—N3—C15—C14	−165.7 (8)
C2—C3—C4—C5	−1.4 (15)	C13—N3—C15—C16	13.6 (14)
C1—N1—C5—C4	−1.3 (14)	C14—C15—C16—C17	−1.8 (13)
Hg1—N1—C5—C4	−176.3 (7)	N3—C15—C16—C17	178.9 (9)
C3—C4—C5—N1	1.1 (16)	C15—C16—C17—C18	−1.9 (15)
C2—N2—C6—C7	73.2 (12)	C16—C17—C18—N4	3.5 (14)
N2—C6—C7—C8	40.2 (13)	C14—N4—C18—C17	−1.4 (12)
N2—C6—C7—C12	−141.5 (9)	Hg1ⁱⁱ—N4—C18—C17	176.7 (7)
C12—C7—C8—C9	−3.4 (15)	C20—N5—C19—O1	0.0 (2)
C6—C7—C8—C9	175.0 (10)	C21—N5—C19—O1	−174 (3)
C7—C8—C9—C10	1.3 (17)	C20'—N5'—C19'—O1'	180.0 (4)
C8—C9—C10—C11	0.4 (15)	C21'—N5'—C19'—O1'	0.0 (3)

Symmetry codes: (i) −x+5/2, y+1/2, −z+3/2; (ii) −x+5/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O1ⁱⁱⁱ	0.88	2.14	3.01 (3)	166
N3—H3N···O1′ⁱⁱⁱ	0.88	2.13	2.98 (3)	162

Symmetry code: (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[HgCl₂(C₁₈H₁₈N₄)]·C₃H₇NO
M_r	634.95
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.4851 (9), 15.1215 (14), 19.490 (2)
β (°)	103.826 (2)
V (Å³)	2428.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.58
Crystal size (mm)	0.15 × 0.11 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.439, 0.531
No. of measured, independent and observed [I > 2σ(I)] reflections	22980, 5479, 2593
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.167, 1.05
No. of reflections	5479
No. of parameters	290
No. of restraints	42
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—N1	2.395 (7)	Hg1—Cl1	2.355 (3)
Hg1—N4ⁱ	2.308 (6)	Hg1—Cl2	2.391 (3)

Symmetry code: (i) −x+5/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

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

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.