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Acta Cryst. (2007). E63, m2191
https://doi.org/10.1107/S1600536807034745
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Diaqua­bis(4-chloro­benzoato-κO)bis-(N,N′-diethyl­nicotinamide-κN)zinc(II)

M. Sarı, G. Gökçe, S. Gökçe, E. Şahin and H. Necefoğlu
The title compound, [Zn(C7H4ClO2)2(C10H14N2O)2(H2O)2], is a monomeric complex, where the ZnII ion resides on a centre of symmetry in an octa­hedral coordination environment comprising two pyridyl N, two carboxyl­ate O and two water O atoms. There is an intra­molecular hydrogen bond linking each water mol­ecule with one carboxylate group.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034745/bg2071sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034745/bg2071Isup2.hkl
Contains datablock I

CCDC reference: 657614

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.063
  • wR factor = 0.169
  • Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found






Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.78 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C14     ..       6.01 su
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C14    -   C15    ...       1.43 Ang.


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn          (2)       1.90


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
Comment top

Zn(II)plays a key role in many biological processes and its interactions are a subject of considerable interest. The metal takes part in more than 300 metalloenzymes and many of its complexes have antimicrobial effect against bacteria, fungi and viruses (Szunyogová et al.; 2007). They are interesting both from a chemical point of view as due to their biological activity (Györyová et al., 1995). In particular, N,N'-Diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972). The structures of some complexes obtained from the reactions of transition metal(II) ions with DENA have been determined previously; (Bigoli et al., 1972; Hökelek et al., 1995; Hökelek & Necefoğlu, 1996, Hökelek & Necefoğlu, 1997).

On the other hand, the structure-function-coordination relationships of the arylcarboxylate ion in Zn(II) complexes of benzoic acid derivatives change depending on the nature and position of the substituted groups in the phenyl ring, the nature of the additional ligand molecule or solvent, and the pH and temperature of synthesis (Shnulin et al., 1981; Adiwidjaja et al., 1978). When pyridine and its derivatives are coordinated instead of water molecules, the structure is completely different (Catterick et al., 1974).

We report here the structure of the title compound, (I), a monomeric zinc complex combining both the chlorobenzoate and diethylnicotinamide ligands.

Fig. 1 shows an ellipsoid plot of (I). The Zn cation is located on a symmetry centre in a slightly distorted octahedral environment. The metal is coordinated by two O atoms from two equivalent carboxylate groups and two O atoms from two water molecules to form a distorted square-planar base (Table 1). Two pyridine N atoms from diethylnicotinamide (DENA) ligands (Table 1), complete the Jahn-Teller distorted octahedral coordination at a longer distance (Zn—N: 2.168 (2) Å), in good agreement with values reported for other octahedrally coordinated ZnII complexes [viz., Zn(DENA)2(NCS)2.2H2O, Zn—N: 2.171 (4) Å; Bigoli et al.,1973]. The carboxylate group is approximately coplanar with the attached benzene ring, the dihedral angle between both planes being 2.8 (3)°. The pyridine and benzene rings are planar, the maximum deviation from the least-squares planes being -0.0072 (10) Å for atom C10 and 0.0006 (1) Å for atom C2. There is an intramolecular hydrogen bond between O1w and the carboxyl O3 (Table 2).

Related literature top

For related literature, see: Adiwidjaja et al. (1978); Bigoli et al. (1972, 1973); Catterick et al. (1974); Györyová et al. (1995); Hökelek & Necefoğlu (1996, 1997); Hökelek et al. (1995); Shnulin et al. (1981); Szunyogová et al. (2007).

Experimental top

In the synthesis of the complex, sodium p-chlorobenzoate was preapared firstly, for what 0.02 mole p-chlorobenzoic acid was reacted with aqueous solution (50 ml) of 0,02 mole sodium bicarbonate. In order to remove completely the carbon dioxide formed in the reaction, the solution was stirred with heating at 363 K for 1 h and allowed to cool at room temperature. In another beaker, an aqueous solution (25 ml) of diethylnicotinamide (0.02 mole) was added to an aqueous solution (25 ml) of zinc nitrate (0,01 mole) and the previously prepared solution of sodium p-chlorobenzoate was added. This final mixed solution was kept unperturbed for 3–5 days, to allow for crystallization. The crystals formed were filtered off, washed with cold water and dried at room temperature. Analysis found: C 52.49, H 5.00, N 7.26%; calculated for C34H40Cl2N4O8Zn: C 53.10, H 5.24, N 7.29%.

Refinement top

Water H atoms were located in difference maps and refined with isotropic displacement factors. Other H atoms were placed in geometrically idealized positions and refined constrained to ride on their parent atoms with distances in the range 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl atoms.

Structure description top

Zn(II)plays a key role in many biological processes and its interactions are a subject of considerable interest. The metal takes part in more than 300 metalloenzymes and many of its complexes have antimicrobial effect against bacteria, fungi and viruses (Szunyogová et al.; 2007). They are interesting both from a chemical point of view as due to their biological activity (Györyová et al., 1995). In particular, N,N'-Diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972). The structures of some complexes obtained from the reactions of transition metal(II) ions with DENA have been determined previously; (Bigoli et al., 1972; Hökelek et al., 1995; Hökelek & Necefoğlu, 1996, Hökelek & Necefoğlu, 1997).

On the other hand, the structure-function-coordination relationships of the arylcarboxylate ion in Zn(II) complexes of benzoic acid derivatives change depending on the nature and position of the substituted groups in the phenyl ring, the nature of the additional ligand molecule or solvent, and the pH and temperature of synthesis (Shnulin et al., 1981; Adiwidjaja et al., 1978). When pyridine and its derivatives are coordinated instead of water molecules, the structure is completely different (Catterick et al., 1974).

We report here the structure of the title compound, (I), a monomeric zinc complex combining both the chlorobenzoate and diethylnicotinamide ligands.

Fig. 1 shows an ellipsoid plot of (I). The Zn cation is located on a symmetry centre in a slightly distorted octahedral environment. The metal is coordinated by two O atoms from two equivalent carboxylate groups and two O atoms from two water molecules to form a distorted square-planar base (Table 1). Two pyridine N atoms from diethylnicotinamide (DENA) ligands (Table 1), complete the Jahn-Teller distorted octahedral coordination at a longer distance (Zn—N: 2.168 (2) Å), in good agreement with values reported for other octahedrally coordinated ZnII complexes [viz., Zn(DENA)2(NCS)2.2H2O, Zn—N: 2.171 (4) Å; Bigoli et al.,1973]. The carboxylate group is approximately coplanar with the attached benzene ring, the dihedral angle between both planes being 2.8 (3)°. The pyridine and benzene rings are planar, the maximum deviation from the least-squares planes being -0.0072 (10) Å for atom C10 and 0.0006 (1) Å for atom C2. There is an intramolecular hydrogen bond between O1w and the carboxyl O3 (Table 2).

For related literature, see: Adiwidjaja et al. (1978); Bigoli et al. (1972, 1973); Catterick et al. (1974); Györyová et al. (1995); Hökelek & Necefoğlu (1996, 1997); Hökelek et al. (1995); Shnulin et al. (1981); Szunyogová et al. (2007).

Computing details top

Data collection: CrstalClear (Rigaku/MSC, 2005); cell refinement: CrstalClear; data reduction: CrstalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular sructure and atomic labelling scheme of the title compound. Hydrogen bonds are indicated by open dashed lines. Displacement ellipsoids are drawn at the 30% probability level.Unlabelled atoms are related to labelled atoms by -x, -y, -z.
Diaquabis(4-chlorobenzoato-κO)bis-(N,N'- diethylnicotinamide-κN)zinc(II) top
Crystal data top
[Zn(C7H4ClO2)2(C10H14N2O)2(H2O)2]Z = 1
Mr = 768.99F(000) = 400
Triclinic, P1Dx = 1.389 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.3570 (2) ÅCell parameters from 25 reflections
b = 8.6887 (10) Åθ = 2.5–30.5°
c = 15.9114 (10) ŵ = 0.87 mm−1
α = 85.047 (5)°T = 296 K
β = 78.476 (5)°Prism, yellow
γ = 67.321 (4)°0.35 × 0.20 × 0.10 mm
V = 919.49 (13) Å3
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer		5615 independent reflections
Radiation source: sealed X-ray tube3800 reflections with I > 2σ(I)
Graphite Monochromator monochromatorRint = 0.073
Detector resolution: 10.000 pixels mm-1θmax = 30.5°, θmin = 2.5°
ω scansh = −10→10
Absorption correction: multi-scan
(Blessing, 1995)		k = −12→12
Tmin = 0.812, Tmax = 0.917l = −22→22
27286 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0647P)2 + 0.5887P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5615 reflectionsΔρmax = 0.85 e Å−3
234 parametersΔρmin = −0.44 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (4)
Crystal data top
[Zn(C7H4ClO2)2(C10H14N2O)2(H2O)2]γ = 67.321 (4)°
Mr = 768.99V = 919.49 (13) Å3
Triclinic, P1Z = 1
a = 7.3570 (2) ÅMo Kα radiation
b = 8.6887 (10) ŵ = 0.87 mm−1
c = 15.9114 (10) ÅT = 296 K
α = 85.047 (5)°0.35 × 0.20 × 0.10 mm
β = 78.476 (5)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer		5615 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		3800 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.917Rint = 0.073
27286 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.85 e Å−3
5615 reflectionsΔρmin = −0.44 e Å−3
234 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.00000.00000.00000.04307 (17)
Cl10.73554 (19)0.1583 (2)−0.46678 (7)0.0998 (4)
O1W0.2219 (3)0.0161 (3)0.06412 (16)0.0526 (5)
H1A0.206 (6)0.113 (5)0.074 (2)0.057 (11)*
H1B0.184 (8)−0.030 (7)0.115 (3)0.112 (19)*
O20.1110 (3)0.1211 (3)−0.10540 (13)0.0477 (5)
O3−0.0778 (3)0.1279 (3)−0.20065 (15)0.0588 (6)
O40.8388 (4)−0.3286 (3)−0.12444 (17)0.0645 (6)
N10.2253 (4)−0.2349 (3)−0.05050 (16)0.0448 (5)
N20.8313 (5)−0.4147 (5)−0.2505 (2)0.0748 (9)
C10.0786 (4)0.1282 (4)−0.18056 (19)0.0430 (6)
C20.2437 (4)0.1359 (4)−0.25251 (19)0.0437 (6)
C30.4176 (5)0.1423 (4)−0.2350 (2)0.0494 (7)
H30.43250.1415−0.17830.059*
C40.5694 (5)0.1500 (5)−0.3001 (2)0.0570 (8)
H40.68560.1547−0.28780.068*
C50.5441 (5)0.1503 (5)−0.3838 (2)0.0616 (9)
C60.3747 (5)0.1419 (5)−0.4034 (2)0.0617 (9)
H60.36100.1416−0.46020.074*
C70.2248 (5)0.1338 (4)−0.3374 (2)0.0526 (7)
H70.11000.1270−0.35000.063*
C80.1959 (4)−0.3783 (4)−0.0406 (2)0.0477 (7)
H80.0743−0.3778−0.00960.057*
C90.3380 (5)−0.5276 (4)−0.0745 (2)0.0549 (8)
H90.3129−0.6253−0.06610.066*
C100.5181 (5)−0.5280 (4)−0.1210 (2)0.0530 (8)
H100.6159−0.6261−0.14520.064*
C110.5511 (4)−0.3795 (4)−0.13123 (19)0.0449 (6)
C120.4022 (4)−0.2380 (4)−0.09404 (19)0.0454 (6)
H120.4256−0.1394−0.09940.055*
C130.7496 (5)−0.3702 (4)−0.1696 (2)0.0513 (7)
C140.7386 (8)−0.4727 (7)−0.3088 (3)0.0960 (15)
H14A0.8306−0.5810−0.33120.115*
H14B0.6181−0.4854−0.27700.115*
C150.6889 (14)−0.3581 (12)−0.3789 (6)0.203 (5)
H15A0.6076−0.2485−0.35690.208*
H15B0.6163−0.3932−0.41200.208*
H15C0.8096−0.3560−0.41460.208*
C161.0387 (7)−0.4206 (6)−0.2822 (3)0.0845 (13)
H16A1.1175−0.4644−0.23730.101*
H16B1.1008−0.4953−0.33070.101*
C171.0383 (9)−0.2539 (7)−0.3086 (4)0.113 (2)
H17A0.9436−0.2030−0.34610.170*
H17B1.1696−0.2639−0.33800.170*
H17C1.0015−0.1860−0.25870.170*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0364 (2)0.0470 (3)0.0430 (3)−0.0135 (2)−0.00279 (18)−0.0062 (2)
Cl10.0809 (7)0.1576 (13)0.0650 (6)−0.0628 (8)0.0159 (5)−0.0051 (7)
O1W0.0482 (12)0.0575 (15)0.0573 (14)−0.0236 (11)−0.0112 (10)−0.0056 (12)
O20.0464 (11)0.0523 (12)0.0432 (11)−0.0187 (10)−0.0041 (9)−0.0039 (9)
O30.0438 (11)0.0772 (16)0.0568 (13)−0.0241 (11)−0.0124 (10)0.0062 (12)
O40.0546 (13)0.0773 (17)0.0705 (16)−0.0328 (13)−0.0093 (12)−0.0138 (13)
N10.0382 (12)0.0461 (14)0.0473 (13)−0.0146 (10)−0.0026 (10)−0.0045 (11)
N20.0625 (18)0.108 (3)0.0594 (18)−0.0429 (19)0.0088 (14)−0.0224 (18)
C10.0395 (13)0.0392 (14)0.0456 (15)−0.0103 (11)−0.0066 (11)−0.0011 (12)
C20.0420 (14)0.0414 (15)0.0452 (15)−0.0136 (12)−0.0064 (11)−0.0020 (12)
C30.0481 (16)0.0536 (18)0.0484 (16)−0.0216 (14)−0.0068 (13)−0.0033 (13)
C40.0489 (17)0.067 (2)0.059 (2)−0.0275 (16)−0.0064 (14)−0.0006 (16)
C50.0564 (19)0.076 (2)0.0484 (18)−0.0264 (18)0.0024 (14)−0.0033 (16)
C60.059 (2)0.078 (2)0.0448 (17)−0.0238 (18)−0.0065 (14)−0.0005 (16)
C70.0481 (16)0.063 (2)0.0480 (17)−0.0212 (15)−0.0105 (13)−0.0009 (14)
C80.0421 (15)0.0508 (17)0.0502 (16)−0.0177 (13)−0.0059 (12)−0.0055 (13)
C90.0503 (17)0.0479 (17)0.067 (2)−0.0197 (14)−0.0063 (15)−0.0078 (15)
C100.0450 (16)0.0480 (17)0.063 (2)−0.0124 (13)−0.0068 (14)−0.0152 (15)
C110.0373 (13)0.0492 (16)0.0455 (15)−0.0124 (12)−0.0066 (11)−0.0072 (13)
C120.0398 (14)0.0452 (15)0.0496 (16)−0.0151 (12)−0.0040 (12)−0.0055 (12)
C130.0420 (15)0.0560 (18)0.0543 (18)−0.0179 (14)−0.0020 (13)−0.0113 (14)
C140.093 (3)0.130 (4)0.069 (3)−0.050 (3)−0.002 (2)−0.011 (3)
C150.155 (9)0.185 (12)0.152 (9)−0.102 (9)−0.100 (8)0.100 (9)
C160.067 (2)0.085 (3)0.093 (3)−0.030 (2)0.017 (2)−0.024 (2)
C170.120 (5)0.090 (4)0.117 (4)−0.047 (3)0.025 (4)−0.006 (3)
Geometric parameters (Å, º) top
Zn—O2i2.097 (2)C6—C71.381 (5)
Zn—O22.097 (2)C6—H60.9300
Zn—O1Wi2.143 (2)C7—H70.9300
Zn—O1W2.143 (2)C8—C91.384 (4)
Zn—N12.168 (2)C8—H80.9300
Zn—N1i2.168 (2)C9—C101.381 (5)
Cl1—C51.746 (4)C9—H90.9300
O1W—H1A0.83 (4)C10—C111.393 (4)
O1W—H1B0.91 (4)C10—H100.9300
O2—C11.257 (3)C11—C121.375 (4)
O3—C11.255 (4)C11—C131.496 (4)
O4—C131.222 (4)C12—H120.9300
N1—C81.336 (4)C14—C151.435 (11)
N1—C121.338 (4)C14—H14A0.9700
N2—C131.328 (4)C14—H14B0.9700
N2—C141.478 (6)C15—H15A0.9600
N2—C161.489 (5)C15—H15B0.9600
C1—C21.511 (4)C15—H15C0.9600
C2—C31.385 (4)C16—C171.473 (7)
C2—C71.387 (4)C16—H16A0.9700
C3—C41.381 (4)C16—H16B0.9700
C3—H30.9300C17—H17A0.9600
C4—C51.382 (5)C17—H17B0.9600
C4—H40.9300C17—H17C0.9600
C5—C61.373 (5)
O2i—Zn—O2180.0C6—C7—H7119.7
O2i—Zn—O1Wi87.86 (9)C2—C7—H7119.7
O2—Zn—O1Wi92.14 (9)N1—C8—C9123.0 (3)
O2i—Zn—O1W92.14 (9)N1—C8—H8118.5
O2—Zn—O1W87.86 (9)C9—C8—H8118.5
O1Wi—Zn—O1W180.00 (11)C10—C9—C8118.5 (3)
O2i—Zn—N191.50 (9)C10—C9—H9120.8
O2—Zn—N188.50 (9)C8—C9—H9120.8
O1Wi—Zn—N193.59 (10)C9—C10—C11119.1 (3)
O1W—Zn—N186.41 (10)C9—C10—H10120.5
O2i—Zn—N1i88.50 (9)C11—C10—H10120.5
O2—Zn—N1i91.50 (9)C12—C11—C10118.3 (3)
O1Wi—Zn—N1i86.41 (10)C12—C11—C13117.8 (3)
O1W—Zn—N1i93.59 (10)C10—C11—C13123.4 (3)
N1—Zn—N1i180.00 (13)N1—C12—C11123.3 (3)
Zn—O1W—H1A114 (3)N1—C12—H12118.4
Zn—O1W—H1B96 (3)C11—C12—H12118.4
H1A—O1W—H1B108 (4)O4—C13—N2120.8 (3)
C1—O2—Zn126.4 (2)O4—C13—C11119.0 (3)
C8—N1—C12117.8 (3)N2—C13—C11120.1 (3)
C8—N1—Zn123.0 (2)C15—C14—N2111.6 (6)
C12—N1—Zn119.1 (2)C15—C14—H14A108.9
C13—N2—C14124.9 (3)N2—C14—H14A108.9
C13—N2—C16117.6 (3)C15—C14—H14B108.9
C14—N2—C16117.4 (3)N2—C14—H14B108.9
O3—C1—O2125.6 (3)H14A—C14—H14B107.7
O3—C1—C2117.6 (3)C14—C15—H15A109.5
O2—C1—C2116.8 (3)C14—C15—H15B109.5
C3—C2—C7118.8 (3)H15A—C15—H15B109.5
C3—C2—C1120.7 (3)C14—C15—H15C109.5
C7—C2—C1120.4 (3)H15A—C15—H15C109.5
C4—C3—C2121.4 (3)H15B—C15—H15C109.5
C4—C3—H3119.3C17—C16—N2111.3 (4)
C2—C3—H3119.3C17—C16—H16A109.4
C3—C4—C5118.2 (3)N2—C16—H16A109.4
C3—C4—H4120.9C17—C16—H16B109.4
C5—C4—H4120.9N2—C16—H16B109.4
C6—C5—C4121.9 (3)H16A—C16—H16B108.0
C6—C5—Cl1119.4 (3)C16—C17—H17A109.5
C4—C5—Cl1118.7 (3)C16—C17—H17B109.5
C5—C6—C7119.0 (3)H17A—C17—H17B109.5
C5—C6—H6120.5C16—C17—H17C109.5
C7—C6—H6120.5H17A—C17—H17C109.5
C6—C7—C2120.7 (3)H17B—C17—H17C109.5
O1Wi—Zn—O2—C1−16.0 (2)C3—C2—C7—C6−1.4 (5)
O1W—Zn—O2—C1164.0 (2)C1—C2—C7—C6179.6 (3)
N1—Zn—O2—C177.5 (2)C12—N1—C8—C9−1.2 (5)
N1i—Zn—O2—C1−102.5 (2)Zn—N1—C8—C9178.5 (2)
O2i—Zn—N1—C832.6 (2)N1—C8—C9—C10−0.4 (5)
O2—Zn—N1—C8−147.4 (2)C8—C9—C10—C110.8 (5)
O1W—Zn—N1—C8124.6 (2)C9—C10—C11—C120.2 (5)
O2i—Zn—N1—C12−147.8 (2)C9—C10—C11—C13171.2 (3)
O2—Zn—N1—C1232.2 (2)C8—N1—C12—C112.3 (4)
O1Wi—Zn—N1—C12124.3 (2)Zn—N1—C12—C11−177.4 (2)
O1W—Zn—N1—C12−55.7 (2)C10—C11—C12—N1−1.8 (5)
Zn—O2—C1—O330.9 (4)C13—C11—C12—N1−173.4 (3)
Zn—O2—C1—C2−148.4 (2)C14—N2—C13—O4177.6 (4)
O3—C1—C2—C3177.8 (3)C16—N2—C13—O43.2 (6)
O2—C1—C2—C3−2.9 (4)C14—N2—C13—C111.0 (6)
O3—C1—C2—C7−3.2 (4)C16—N2—C13—C11−173.4 (4)
O2—C1—C2—C7176.1 (3)C12—C11—C13—O457.2 (4)
C7—C2—C3—C41.3 (5)C10—C11—C13—O4−113.9 (4)
C1—C2—C3—C4−179.8 (3)C12—C11—C13—N2−126.1 (4)
C2—C3—C4—C5−0.3 (5)C10—C11—C13—N262.8 (5)
C3—C4—C5—C6−0.6 (6)C13—N2—C14—C15114.2 (7)
C3—C4—C5—Cl1−179.5 (3)C16—N2—C14—C15−70.5 (8)
C4—C5—C6—C70.4 (6)C13—N2—C16—C17−82.4 (6)
Cl1—C5—C6—C7179.3 (3)C14—N2—C16—C17102.7 (5)
C5—C6—C7—C20.6 (6)
Symmetry code: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O3i0.91 (5)1.75 (5)2.654 (4)168 (5)
Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula[Zn(C7H4ClO2)2(C10H14N2O)2(H2O)2]
Mr768.99
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.3570 (2), 8.6887 (10), 15.9114 (10)
α, β, γ (°)85.047 (5), 78.476 (5), 67.321 (4)
V (Å3)919.49 (13)
Z1
Radiation typeMo Kα
µ (mm−1)0.87
Crystal size (mm)0.35 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID-S
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.812, 0.917
No. of measured, independent and
observed [I > 2σ(I)] reflections		27286, 5615, 3800
Rint0.073
(sin θ/λ)max (Å−1)0.715
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.169, 1.02
No. of reflections5615
No. of parameters234
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.85, −0.44

Computer programs: CrstalClear (Rigaku/MSC, 2005), CrstalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected bond lengths (Å) top
Zn—O22.097 (2)Zn—N12.168 (2)
Zn—O1W2.143 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O3i0.91 (5)1.75 (5)2.654 (4)168 (5)
Symmetry code: (i) −x, −y, −z.
 

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