Chlorido[(E)-2-hydr­oxy-6-(isonicotinoyl­hydrazonometh­yl)phen­yl]mercury(II) monohydrate

Bai, S.-Z.; Lou, X.-H.; Li, H.-M.; Shi, H.

doi:10.1107/S1600536809023824

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m842-m843

doi:10.1107/S1600536809023824

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Chlorido[(E)-2-hydroxy-6-(isonicotinoylhydrazonomethyl)phenyl]mercury(II) monohydrate

Su-Zhen Bai,^a Xin-Hua Lou,^b ^* Hong-Mei Li ^c and Hui Shi ^a

^aCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467002, People's Republic of China, ^bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^cChemical Engineering and Pharmaceutics School, Henan University of Science and Technology, Luoyang 471003, People's Republic of China
^*Correspondence e-mail: lxh-9802@163.com

(Received 12 June 2009; accepted 22 June 2009; online 27 June 2009)

The asymmetric unit of the title compound, [Hg(C₁₃H₁₀N₃O₂)Cl]·H₂O, contains two independent mercury(II) complexes with slightly different conformations, related via a pseudo-inversion centre, and two water molecules. The Hg^II atoms show a typical linear geometry to a C atom of the benzene ring and to a Cl atom. A benzene C and the azomethine N atom chelate the Hg^II atoms with weak intramolecular Hg⋯N bonding distances of 2.735 (3) and 2.739 (3) Å, respectively. The resulting five-membered metallacycles are nearly coplanar with the benzene rings [dihedral angles = 0.9 (1) and 0.7 (1)°], while the pyridine rings make dihedral angles with the benzene units of 58.17 (1) and 56.58 (1)°. In the crystal structure, the Hg^II complexes are linked by hydroxy donor and pyridine acceptor groups into chains along [010]. The water molecules connect the complexes through intermolecular O—H⋯O_carbonyl bonds in the a-axis direction, and the azomethine H atoms donate towards the water O atoms, forming a three-dimensional network of intermolecular O—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background, see: Gruter et al. (1995 ); Soro et al. (2005 ); Xu et al. (2009b ). For related structures, see: Hao et al. (2007 ); Lin et al. (2002 ); For the synthesis of related cyclomercurated compounds, see: Xu et al. (2009a ).

Experimental

Crystal data

[Hg(C₁₃H₁₀N₃O₂)Cl]·H₂O
M_r = 494.30
Monoclinic, P 2₁ /n
a = 14.5932 (16) Å
b = 14.0111 (15) Å
c = 15.3711 (17) Å
β = 104.6850 (10)°
V = 3040.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 10.31 mm⁻¹
T = 296 K
0.37 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.113, T_max = 0.179 (expected range = 0.048–0.076)
22798 measured reflections
5658 independent reflections
4683 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.046
S = 1.05
5658 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H4W⋯O2ⁱ	0.83	2.15	2.898 (4)	150
O6—H3W⋯O3	0.83	2.30	3.023 (4)	146
O5—H2W⋯O1	0.83	2.17	2.963 (4)	159
O5—H1W⋯O4ⁱⁱ	0.84	2.06	2.876 (4)	166
N5—H5D⋯O6ⁱⁱⁱ	0.86	2.04	2.872 (4)	162
N2—H2D⋯O5^iv	0.86	2.06	2.890 (4)	161
O3—H3⋯N6^v	0.82	1.92	2.737 (4)	171
O1—H1⋯N3^vi	0.82	1.93	2.733 (4)	167
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x, y-1, z; (vi) x, y+1, z.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023824/si2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023824/si2184Isup2.hkl

checkCIF report

Comment top

Cyclometallated compounds have attracted much research interest owing to theirs utility in synthesis, catalysis and materials (Gruter et al., 1995; Xu et al., 2009b). Among them, cyclomercurated compounds are easy to prepare through a C—H activation process and are stable but reasonably reactive. Although numerous cyclomercurated compounds have been widely investigated, and many examples have been reported(Soro et al., 2005; Hao et al., 2007), only a few cyclometallated Schiff bases containing heterocyclic ring are known(Lin et al., 2002).

The asymmetric unit of the title compound (Fig.1) contains two independent mercury(II) complexes with slightly different conformations, related via a pseudo-inversion centre (1/2a, 3/4b, 1/4c), and two water molecules. The Hg^II atoms show a typical linear coordination geometry with a carbon atom of the benzene ring and the chloride atom in trans position. A benzene carbon and the azomethine nitrogen atom chelate the mercury(II) atoms with weak intramolecular Hg···N bonding distances of 2.735 (3)Å and 2.739 (3) Å. which are shorter than those of the related Hg^II complex (Hao et al., (2007); Lin et al., (2002); Xu et al., (2009a). The C—Hg and Hg—Cl bond distances are within normal ranges. The C1—Hg1—Cl1 and C14—Hg2—Cl2 angles are 173.85 (10)° and 174.67 (10)°, slightly smaller than the ideal value of 180° in organic derivatives of mercury. The resulting five-membered metallacycles are nearly coplanar with the benzene ring, while the pyridine are not coplanar with the benzene. In the crystal structure, intermolecular O—H···O, N—H···O and O—H···N hydrogen bonds (Table 1) link the independent Hg^II complexes and the water molecules into a three-dimensional network.

Related literature top

For general background, see: Gruter et al. (1995); Soro et al. (2005); Xu et al. (2009b). For related structures, see: Hao et al. (2007); Lin et al. (2002); For the synthesis, see: Xu et al. (2009a).

Experimental top

Chlorido(2-formyl-6-hydroxybenzaldehyde-kC¹)mercury(II) was synthesized according to the reported procedure (Xu et al., 2009a). The title compound was prepared from the above compound with isonicotinoylhydrazine and recrystallized from ethanol solution at room temperature to give the desired product as colourless crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.

Chlorido[(E)-2-hydroxy-6-(isonicotinoylhydrazonomethyl)phenyl]mercury(II) monohydrate top

Crystal data top

[Hg(C₁₃H₁₀N₃O₂)Cl]·H₂O	F(000) = 1856
M_r = 494.30	D_x = 2.160 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.5932 (16) Å	Cell parameters from 5064 reflections
b = 14.0111 (15) Å	θ = 2.7–28.3°
c = 15.3711 (17) Å	µ = 10.31 mm⁻¹
β = 104.685 (1)°	T = 296 K
V = 3040.2 (6) Å³	Block, colorless
Z = 8	0.37 × 0.28 × 0.25 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5658 independent reflections
Radiation source: fine-focus sealed tube	4683 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.113, T_max = 0.179	k = −16→16
22798 measured reflections	l = −16→18

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.046	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0197P)² + 1.3364P] where P = (F_o² + 2F_c²)/3
5658 reflections	(Δ/σ)_max = 0.002
381 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Hg(C₁₃H₁₀N₃O₂)Cl]·H₂O	V = 3040.2 (6) Å³
M_r = 494.30	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.5932 (16) Å	µ = 10.31 mm⁻¹
b = 14.0111 (15) Å	T = 296 K
c = 15.3711 (17) Å	0.37 × 0.28 × 0.25 mm
β = 104.685 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5658 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4683 reflections with I > 2σ(I)
T_min = 0.113, T_max = 0.179	R_int = 0.030
22798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.046	H-atom parameters constrained
S = 1.05	Δρ_max = 0.52 e Å⁻³
5658 reflections	Δρ_min = −0.83 e Å⁻³
381 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Hg1	0.909422 (9)	0.795528 (10)	0.140566 (10)	0.03271 (5)
Hg2	0.088755 (10)	0.667392 (10)	0.363229 (10)	0.03354 (5)
Cl1	1.06292 (6)	0.74039 (8)	0.15848 (7)	0.0482 (3)
Cl2	−0.06489 (7)	0.72341 (8)	0.34424 (7)	0.0485 (3)
O1	0.85291 (17)	1.00819 (18)	0.13735 (19)	0.0444 (7)
H1	0.8409	1.0641	0.1231	0.067*
O2	0.91602 (18)	0.54581 (19)	0.0795 (2)	0.0539 (8)
O3	0.14451 (18)	0.45504 (17)	0.3573 (2)	0.0473 (7)
H3	0.1565	0.3987	0.3693	0.071*
O4	0.08053 (18)	0.91980 (18)	0.4187 (2)	0.0494 (7)
N1	0.7764 (2)	0.6537 (2)	0.1123 (2)	0.0339 (7)
N2	0.7733 (2)	0.55515 (19)	0.11402 (19)	0.0338 (7)
H2D	0.7253	0.5255	0.1239	0.041*
N3	0.8374 (2)	0.2013 (2)	0.1131 (2)	0.0397 (8)
N4	0.2225 (2)	0.8089 (2)	0.3911 (2)	0.0362 (7)
N5	0.2266 (2)	0.9077 (2)	0.39086 (19)	0.0352 (7)
H5D	0.2760	0.9368	0.3836	0.042*
N6	0.1645 (2)	1.2624 (2)	0.3851 (2)	0.0397 (8)
C1	0.7779 (2)	0.8579 (2)	0.1197 (2)	0.0279 (8)
C2	0.7707 (3)	0.9568 (3)	0.1195 (2)	0.0349 (8)
C3	0.6823 (3)	1.0005 (3)	0.1066 (3)	0.0431 (10)
H3A	0.6779	1.0667	0.1076	0.052*
C4	0.6011 (3)	0.9454 (3)	0.0924 (3)	0.0495 (11)
H4	0.5422	0.9746	0.0830	0.059*
C5	0.6075 (3)	0.8465 (3)	0.0920 (3)	0.0411 (9)
H5	0.5528	0.8097	0.0830	0.049*
C6	0.6953 (2)	0.8023 (2)	0.1051 (2)	0.0313 (8)
C7	0.6986 (3)	0.6972 (2)	0.1046 (2)	0.0331 (8)
H7	0.6430	0.6625	0.0986	0.040*
C8	0.8484 (3)	0.5069 (2)	0.0996 (2)	0.0351 (9)
C9	0.8433 (2)	0.4003 (2)	0.1063 (2)	0.0302 (8)
C10	0.8804 (2)	0.3447 (2)	0.0486 (3)	0.0361 (9)
H10	0.9089	0.3731	0.0075	0.043*
C11	0.8744 (2)	0.2467 (3)	0.0532 (3)	0.0379 (9)
H11	0.8973	0.2102	0.0127	0.046*
C12	0.8025 (3)	0.2558 (3)	0.1688 (3)	0.0416 (9)
H12	0.7760	0.2254	0.2104	0.050*
C13	0.8035 (3)	0.3542 (3)	0.1680 (3)	0.0393 (9)
H13	0.7782	0.3890	0.2079	0.047*
C14	0.2197 (2)	0.6052 (2)	0.3792 (2)	0.0291 (8)
C15	0.3026 (3)	0.6602 (2)	0.3951 (2)	0.0324 (8)
C16	0.3903 (3)	0.6153 (3)	0.4047 (3)	0.0446 (10)
H16	0.4453	0.6518	0.4149	0.054*
C17	0.3955 (3)	0.5171 (3)	0.3992 (3)	0.0510 (11)
H17	0.4540	0.4876	0.4057	0.061*
C18	0.3143 (3)	0.4625 (3)	0.3840 (3)	0.0447 (10)
H18	0.3180	0.3965	0.3798	0.054*
C19	0.2271 (3)	0.5063 (3)	0.3751 (2)	0.0350 (9)
C20	0.3007 (3)	0.7648 (3)	0.3986 (2)	0.0361 (9)
H20	0.3568	0.7992	0.4063	0.043*
C21	0.1510 (2)	0.9574 (3)	0.4023 (2)	0.0352 (8)
C22	0.1583 (2)	1.0639 (2)	0.3948 (2)	0.0305 (8)
C23	0.1992 (3)	1.1083 (3)	0.3340 (2)	0.0381 (9)
H23	0.2259	1.0727	0.2955	0.046*
C24	0.1997 (3)	1.2072 (2)	0.3315 (3)	0.0392 (9)
H24	0.2265	1.2367	0.2896	0.047*
C25	0.1267 (3)	1.2190 (3)	0.4458 (3)	0.0386 (9)
H25	0.1036	1.2567	0.4854	0.046*
C26	0.1205 (2)	1.1212 (3)	0.4521 (2)	0.0372 (9)
H26	0.0919	1.0936	0.4935	0.045*
O5	0.89687 (19)	0.9980 (2)	0.33618 (19)	0.0566 (8)
H1W	0.9471	0.9752	0.3683	0.085*
H2W	0.9002	1.0018	0.2829	0.085*
O6	0.10303 (19)	0.4671 (2)	0.1547 (2)	0.0618 (8)
H3W	0.0890	0.4581	0.2031	0.093*
H4W	0.0571	0.4882	0.1161	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.03055 (8)	0.02692 (10)	0.04319 (9)	0.00303 (6)	0.01399 (6)	0.00319 (6)
Hg2	0.03092 (8)	0.02783 (10)	0.04418 (9)	0.00243 (6)	0.01377 (6)	0.00243 (6)
Cl1	0.0326 (5)	0.0563 (7)	0.0615 (7)	0.0070 (4)	0.0225 (5)	0.0088 (5)
Cl2	0.0337 (5)	0.0583 (7)	0.0585 (7)	0.0064 (4)	0.0213 (5)	0.0088 (5)
O1	0.0416 (15)	0.0241 (15)	0.0673 (19)	−0.0017 (11)	0.0136 (14)	0.0059 (13)
O2	0.0427 (16)	0.0345 (16)	0.092 (2)	−0.0030 (12)	0.0304 (16)	0.0051 (15)
O3	0.0496 (17)	0.0181 (14)	0.074 (2)	0.0002 (12)	0.0163 (14)	0.0048 (14)
O4	0.0429 (16)	0.0295 (16)	0.081 (2)	−0.0021 (12)	0.0254 (15)	0.0056 (14)
N1	0.0407 (18)	0.0175 (16)	0.0423 (18)	0.0007 (13)	0.0085 (15)	0.0004 (13)
N2	0.0329 (16)	0.0204 (17)	0.0505 (19)	−0.0019 (12)	0.0151 (14)	−0.0009 (13)
N3	0.045 (2)	0.026 (2)	0.047 (2)	0.0007 (13)	0.0098 (16)	0.0011 (14)
N4	0.0443 (19)	0.0212 (17)	0.0430 (19)	−0.0063 (14)	0.0108 (15)	−0.0037 (14)
N5	0.0349 (17)	0.0217 (17)	0.0505 (19)	−0.0045 (13)	0.0135 (14)	−0.0018 (14)
N6	0.0408 (18)	0.0281 (19)	0.050 (2)	0.0005 (14)	0.0120 (16)	0.0004 (15)
C1	0.0333 (19)	0.0218 (19)	0.0300 (19)	0.0068 (14)	0.0103 (15)	0.0038 (14)
C2	0.040 (2)	0.028 (2)	0.037 (2)	0.0015 (16)	0.0096 (17)	0.0025 (16)
C3	0.048 (2)	0.025 (2)	0.057 (3)	0.0112 (18)	0.014 (2)	0.0000 (18)
C4	0.042 (2)	0.041 (3)	0.063 (3)	0.0197 (19)	0.010 (2)	0.004 (2)
C5	0.032 (2)	0.035 (2)	0.054 (3)	−0.0009 (16)	0.0046 (18)	0.0005 (18)
C6	0.036 (2)	0.025 (2)	0.034 (2)	0.0047 (15)	0.0097 (16)	−0.0003 (15)
C7	0.037 (2)	0.025 (2)	0.038 (2)	−0.0028 (15)	0.0117 (17)	−0.0013 (16)
C8	0.036 (2)	0.024 (2)	0.044 (2)	−0.0021 (16)	0.0075 (17)	0.0039 (16)
C9	0.0301 (18)	0.021 (2)	0.037 (2)	0.0014 (14)	0.0052 (15)	0.0032 (15)
C10	0.037 (2)	0.029 (2)	0.044 (2)	−0.0006 (16)	0.0154 (18)	0.0009 (17)
C11	0.039 (2)	0.030 (2)	0.046 (2)	0.0082 (16)	0.0132 (18)	−0.0025 (18)
C12	0.049 (2)	0.037 (3)	0.042 (2)	−0.0021 (18)	0.0186 (19)	0.0061 (19)
C13	0.052 (2)	0.024 (2)	0.044 (2)	0.0024 (17)	0.0164 (19)	−0.0021 (17)
C14	0.0347 (19)	0.023 (2)	0.0320 (19)	0.0054 (14)	0.0118 (16)	0.0031 (15)
C15	0.038 (2)	0.026 (2)	0.033 (2)	0.0030 (15)	0.0092 (17)	0.0014 (15)
C16	0.034 (2)	0.040 (3)	0.057 (3)	0.0023 (17)	0.0062 (19)	−0.0017 (19)
C17	0.038 (2)	0.041 (3)	0.070 (3)	0.0165 (18)	0.006 (2)	0.005 (2)
C18	0.048 (2)	0.026 (2)	0.058 (3)	0.0120 (18)	0.009 (2)	0.0042 (18)
C19	0.041 (2)	0.023 (2)	0.040 (2)	−0.0009 (16)	0.0077 (17)	0.0044 (16)
C20	0.034 (2)	0.028 (2)	0.046 (2)	−0.0025 (16)	0.0108 (17)	−0.0024 (17)
C21	0.031 (2)	0.032 (2)	0.041 (2)	−0.0013 (16)	0.0066 (17)	−0.0004 (17)
C22	0.0282 (18)	0.023 (2)	0.039 (2)	0.0017 (14)	0.0065 (16)	0.0007 (16)
C23	0.047 (2)	0.034 (2)	0.037 (2)	0.0030 (17)	0.0175 (18)	−0.0026 (17)
C24	0.050 (2)	0.026 (2)	0.046 (2)	−0.0040 (16)	0.0194 (19)	0.0040 (17)
C25	0.040 (2)	0.030 (2)	0.048 (2)	0.0069 (16)	0.0135 (19)	−0.0033 (17)
C26	0.034 (2)	0.040 (2)	0.041 (2)	0.0041 (16)	0.0151 (17)	0.0042 (17)
O5	0.0477 (17)	0.068 (2)	0.0577 (19)	0.0121 (15)	0.0196 (15)	0.0016 (15)
O6	0.0449 (17)	0.072 (2)	0.071 (2)	0.0108 (15)	0.0201 (16)	−0.0060 (17)

Geometric parameters (Å, º) top

Hg1—C1	2.059 (3)	C8—C9	1.501 (5)
Hg1—Cl1	2.3189 (9)	C9—C13	1.390 (5)
Hg2—C14	2.058 (3)	C9—C10	1.389 (5)
Hg2—Cl2	2.3231 (10)	C10—C11	1.379 (5)
O1—C2	1.366 (4)	C10—H10	0.9300
O1—H1	0.8200	C11—H11	0.9300
O2—C8	1.233 (4)	C12—C13	1.379 (5)
O3—C19	1.369 (4)	C12—H12	0.9300
O3—H3	0.8200	C13—H13	0.9300
O4—C21	1.237 (4)	C14—C19	1.391 (5)
N1—C7	1.268 (4)	C14—C15	1.402 (5)
N1—N2	1.382 (4)	C15—C16	1.400 (5)
N2—C8	1.354 (4)	C15—C20	1.468 (5)
N2—H2D	0.8600	C16—C17	1.383 (5)
N3—C12	1.340 (5)	C16—H16	0.9300
N3—C11	1.341 (5)	C17—C18	1.379 (5)
N4—C20	1.277 (4)	C17—H17	0.9300
N4—N5	1.386 (4)	C18—C19	1.389 (5)
N5—C21	1.353 (4)	C18—H18	0.9300
N5—H5D	0.8600	C20—H20	0.9300
N6—C24	1.323 (4)	C21—C22	1.502 (5)
N6—C25	1.345 (4)	C22—C23	1.379 (5)
C1—C2	1.388 (5)	C22—C26	1.402 (5)
C1—C6	1.405 (5)	C23—C24	1.387 (5)
C2—C3	1.397 (5)	C23—H23	0.9300
C3—C4	1.384 (5)	C24—H24	0.9300
C3—H3A	0.9300	C25—C26	1.378 (5)
C4—C5	1.389 (5)	C25—H25	0.9300
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.392 (5)	O5—H1W	0.8363
C5—H5	0.9300	O5—H2W	0.8344
C6—C7	1.473 (5)	O6—H3W	0.8298
C7—H7	0.9300	O6—H4W	0.8293

C1—Hg1—Cl1	173.85 (10)	N3—C12—C13	123.8 (3)
C14—Hg2—Cl2	174.67 (10)	N3—C12—H12	118.1
C2—O1—H1	109.5	C13—C12—H12	118.1
C19—O3—H3	109.5	C12—C13—C9	118.5 (3)
C7—N1—N2	116.7 (3)	C12—C13—H13	120.7
C8—N2—N1	117.6 (3)	C9—C13—H13	120.7
C8—N2—H2D	121.2	C19—C14—C15	118.8 (3)
N1—N2—H2D	121.2	C19—C14—Hg2	119.7 (3)
C12—N3—C11	117.0 (3)	C15—C14—Hg2	121.4 (2)
C20—N4—N5	116.5 (3)	C16—C15—C14	119.8 (3)
C21—N5—N4	118.5 (3)	C16—C15—C20	118.0 (3)
C21—N5—H5D	120.7	C14—C15—C20	122.2 (3)
N4—N5—H5D	120.7	C17—C16—C15	120.2 (4)
C24—N6—C25	117.4 (3)	C17—C16—H16	119.9
C2—C1—C6	119.5 (3)	C15—C16—H16	119.9
C2—C1—Hg1	119.4 (3)	C18—C17—C16	120.2 (4)
C6—C1—Hg1	121.1 (2)	C18—C17—H17	119.9
O1—C2—C1	117.6 (3)	C16—C17—H17	119.9
O1—C2—C3	122.0 (3)	C17—C18—C19	119.9 (4)
C1—C2—C3	120.3 (3)	C17—C18—H18	120.0
C4—C3—C2	120.0 (4)	C19—C18—H18	120.0
C4—C3—H3A	120.0	O3—C19—C18	121.7 (3)
C2—C3—H3A	120.0	O3—C19—C14	117.2 (3)
C3—C4—C5	120.2 (3)	C18—C19—C14	121.0 (3)
C3—C4—H4	119.9	N4—C20—C15	120.3 (3)
C5—C4—H4	119.9	N4—C20—H20	119.9
C4—C5—C6	120.2 (3)	C15—C20—H20	119.9
C4—C5—H5	119.9	O4—C21—N5	123.6 (3)
C6—C5—H5	119.9	O4—C21—C22	121.2 (3)
C5—C6—C1	119.8 (3)	N5—C21—C22	115.2 (3)
C5—C6—C7	118.3 (3)	C23—C22—C26	118.4 (3)
C1—C6—C7	121.9 (3)	C23—C22—C21	123.4 (3)
N1—C7—C6	120.6 (3)	C26—C22—C21	118.3 (3)
N1—C7—H7	119.7	C22—C23—C24	118.3 (3)
C6—C7—H7	119.7	C22—C23—H23	120.8
O2—C8—N2	123.6 (3)	C24—C23—H23	120.8
O2—C8—C9	121.0 (3)	N6—C24—C23	124.1 (3)
N2—C8—C9	115.4 (3)	N6—C24—H24	117.9
C13—C9—C10	118.2 (3)	C23—C24—H24	117.9
C13—C9—C8	123.1 (3)	N6—C25—C26	122.9 (3)
C10—C9—C8	118.7 (3)	N6—C25—H25	118.6
C11—C10—C9	119.1 (3)	C26—C25—H25	118.6
C11—C10—H10	120.5	C25—C26—C22	118.8 (3)
C9—C10—H10	120.5	C25—C26—H26	120.6
N3—C11—C10	123.3 (3)	C22—C26—H26	120.6
N3—C11—H11	118.4	H1W—O5—H2W	110.1
C10—C11—H11	118.4	H3W—O6—H4W	111.0

C7—N1—N2—C8	163.9 (3)	C8—C9—C13—C12	−179.9 (3)
C20—N4—N5—C21	−166.2 (3)	Cl2—Hg2—C14—C19	2.9 (12)
Cl1—Hg1—C1—C2	−23.9 (11)	Cl2—Hg2—C14—C15	−176.6 (8)
Cl1—Hg1—C1—C6	155.6 (7)	C19—C14—C15—C16	1.2 (5)
C6—C1—C2—O1	177.6 (3)	Hg2—C14—C15—C16	−179.3 (3)
Hg1—C1—C2—O1	−2.8 (4)	C19—C14—C15—C20	178.7 (3)
C6—C1—C2—C3	1.2 (5)	Hg2—C14—C15—C20	−1.8 (5)
Hg1—C1—C2—C3	−179.2 (3)	C14—C15—C16—C17	−0.4 (6)
O1—C2—C3—C4	−177.4 (4)	C20—C15—C16—C17	−178.0 (4)
C1—C2—C3—C4	−1.1 (6)	C15—C16—C17—C18	0.1 (6)
C2—C3—C4—C5	0.8 (6)	C16—C17—C18—C19	−0.6 (6)
C3—C4—C5—C6	−0.6 (6)	C17—C18—C19—O3	178.0 (4)
C4—C5—C6—C1	0.8 (6)	C17—C18—C19—C14	1.4 (6)
C4—C5—C6—C7	179.7 (3)	C15—C14—C19—O3	−178.5 (3)
C2—C1—C6—C5	−1.1 (5)	Hg2—C14—C19—O3	2.1 (4)
Hg1—C1—C6—C5	179.4 (3)	C15—C14—C19—C18	−1.7 (5)
C2—C1—C6—C7	−179.9 (3)	Hg2—C14—C19—C18	178.8 (3)
Hg1—C1—C6—C7	0.5 (5)	N5—N4—C20—C15	−177.1 (3)
N2—N1—C7—C6	178.0 (3)	C16—C15—C20—N4	−179.3 (4)
C5—C6—C7—N1	176.9 (3)	C14—C15—C20—N4	3.2 (5)
C1—C6—C7—N1	−4.2 (5)	N4—N5—C21—O4	4.8 (5)
N1—N2—C8—O2	−4.8 (5)	N4—N5—C21—C22	−175.9 (3)
N1—N2—C8—C9	177.4 (3)	O4—C21—C22—C23	−143.1 (4)
O2—C8—C9—C13	145.8 (4)	N5—C21—C22—C23	37.6 (5)
N2—C8—C9—C13	−36.3 (5)	O4—C21—C22—C26	36.2 (5)
O2—C8—C9—C10	−33.8 (5)	N5—C21—C22—C26	−143.1 (3)
N2—C8—C9—C10	144.1 (3)	C26—C22—C23—C24	−1.0 (5)
C13—C9—C10—C11	1.5 (5)	C21—C22—C23—C24	178.3 (3)
C8—C9—C10—C11	−178.9 (3)	C25—N6—C24—C23	0.5 (6)
C12—N3—C11—C10	2.0 (5)	C22—C23—C24—N6	1.1 (6)
C9—C10—C11—N3	−2.5 (5)	C24—N6—C25—C26	−2.2 (5)
C11—N3—C12—C13	−0.6 (5)	N6—C25—C26—C22	2.3 (5)
N3—C12—C13—C9	−0.2 (6)	C23—C22—C26—C25	−0.6 (5)
C10—C9—C13—C12	−0.3 (5)	C21—C22—C26—C25	−179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H4W···O2ⁱ	0.83	2.15	2.898 (4)	150
O6—H3W···O3	0.83	2.30	3.023 (4)	146
O5—H2W···O1	0.83	2.17	2.963 (4)	159
O5—H1W···O4ⁱⁱ	0.84	2.06	2.876 (4)	166
N5—H5D···O6ⁱⁱⁱ	0.86	2.04	2.872 (4)	162
N2—H2D···O5^iv	0.86	2.06	2.890 (4)	161
O3—H3···N6^v	0.82	1.92	2.737 (4)	171
O1—H1···N3^vi	0.82	1.93	2.733 (4)	167

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) x, y−1, z; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Hg(C₁₃H₁₀N₃O₂)Cl]·H₂O
M_r	494.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.5932 (16), 14.0111 (15), 15.3711 (17)
β (°)	104.685 (1)
V (Å³)	3040.2 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	10.31
Crystal size (mm)	0.37 × 0.28 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.113, 0.179
No. of measured, independent and observed [I > 2σ(I)] reflections	22798, 5658, 4683
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.046, 1.05
No. of reflections	5658
No. of parameters	381
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.83

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H4W···O2ⁱ	0.83	2.15	2.898 (4)	150.3
O6—H3W···O3	0.83	2.30	3.023 (4)	145.5
O5—H2W···O1	0.83	2.17	2.963 (4)	158.8
O5—H1W···O4ⁱⁱ	0.84	2.06	2.876 (4)	166.2
N5—H5D···O6ⁱⁱⁱ	0.86	2.04	2.872 (4)	161.9
N2—H2D···O5^iv	0.86	2.06	2.890 (4)	161.1
O3—H3···N6^v	0.82	1.92	2.737 (4)	170.7
O1—H1···N3^vi	0.82	1.93	2.733 (4)	166.6

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) x, y−1, z; (vi) x, y+1, z.

Acknowledgements

This work was supported by the High-Level Personnel to Start Research Fund of Pingdingshan University (No. 2006044).

References

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gruter, G. M., Van Klink, G. P. M., Akkerman, O. S. & Bickelhaupt, F. (1995). Chem. Rev. 95, 2405–2456 CrossRef CAS Web of Science Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 7| July 2009| Pages m842-m843

doi:10.1107/S1600536809023824

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

Chlorido[(E)-2-hydr­­oxy-6-(isonicotinoyl­hydrazonometh­yl)phen­yl]mercury(II) monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Chlorido[(E)-2-hydroxy-6-(isonicotinoylhydrazonomethyl)phenyl]mercury(II) monohydrate