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Acta Cryst. (2006). C62, m13-m15
https://doi.org/10.1107/S0108270105038047
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Diaqua­malonato(1,10-phenanthro­line)­zinc(II)

X.-C. Fu, M.-T. Li, C.-G. Wang and X.-Y. Wang
In the crystal structure of the title complex, [Zn(C3H2O4)(C12H8N2)(H2O)2], the ZnII atom displays a distorted octa­hedral geometry, being coordinated by two N atoms from the 1,10-phenanthroline ligand, two O atoms from different carboxyl­ate groups of the chelating malonate dianion and two O atoms of cis water mol­ecules. The complex mol­ecules are linked to form a three-dimensional supramolecular array by both hydrogen-bonding inter­actions between coordinated water molecules and the uncoordinated carboxyl­ate O atoms of neighboring mol­ecules, and aromatic [pi]-[pi] stacking inter­actions between neighboring phenanthroline rings.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105038047/sf1018sup1.cif
Contains datablocks global, 050520et1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105038047/sf1018Isup2.hkl
Contains datablock I

CCDC reference: 274937

Comment top

There has been considerable interest in the design and synthesis of transition metal complexes with carboxylate ligands in coordination chemistry, as a result of the fact that this type of complex has potential application in molecular-based magnets, catalysis, supramolecular chemistry and biological systems (Li et al., 2002; Shi et al., 2000; Devereux et al., 2000). As an important dicarboxylate ligand, the malonate dianion may acts in a chelating bidentate manner and adopt different carboxylate bridging coordination modes, such as syn/syn, syn/anti and anti/anti (Li et al., 1997; Lightfoot et al.,1999; Lis et al., 1979; Muro et al., 1998). ZnII complexes with the malonate ligand have potential applications in modified metalloenzymes and in precursor systems for Zn-containing ceramic materials. Serval structures of ZnII complexes with malonate (mal) have been reported, viz. {Na2[Zn(mal)2·2H2O}n (Lin et al., 2003), Zn2(mal)2(pym)(H2O)]n.nH2O (pym is pyrimidine; Delgado et al., 2003) and [Zn2(H2O)2(mal)2(C4H4N2)] (Zhang et al., 2003). These structures were all found to be polymeric, with the malonate ligands serving as bridges. To the best of our knowledge, no mononuclear ZnII complexes with the malonate ligand in which malonate acts as a dicarboxylate chelating ligand have been reported. We report here the crystal structure of one such complex, diaquamalonato(1,10-phenanthroline)zinc(II), (I), with a dicaboxylate chelating malonate ligand.

The molecular structure of (I), shown in Fig. 1, consists of discrete monomers. A malonate dianion chelates the ZnII atom through two O atoms from different carboxylate groups. The ZnII atom is also coordinated by the two 1,10-phenanthroline N atoms and two O atoms of two cis water molecules. Each malonate ligand forms a six-membered chelate ring with one ZnII ion in a boat-type configuration; the malonate ligand acts only as a chelating ligand and does not act as a bridge between metal atoms. The carboxylate chelating coordination mode is similar to those of [Mn(mal)(bipy)(H2O)2] (bipy is 2,2'-bipyridine; Sain et al., 2003) and [Mn(mal)(phen)(H2O)2] (phen is 1,10-phenanthroline; Zhang et al.,2004). The ZnII atom exhibits a distorted octahedral coordination sphere with the bond angles ranging from 166.21 (6) to 172.07 (6)° for trans angles and from 77.05 (6) to 99.19 (6)° for the other bond angles (Table 1). The Zn—O(carboxylate) bond distances are 2.0618 (13) and 2.0646 (15) Å. In [Zn2(H2O)2(mal)2(C4H4N2)] (Zhang et al., 2003), the corresponding Zn—O(carboxylate) bond distances are 2.085 (2) and 2.082 (3) Å; the difference is probably due to the effect of the chelating coordination in (I). The Zn—O(water) distances of 2.1152 (17) and 2.1364 (16) Å are comparable to those found in [Zn2(mal)2(pym)(H2O)]n.nH2O [2.175 (4) Å; Delgado et al., 2003]. The Zn—N bond lengths are 2.1601 (17) and 2.1745 (17) Å, somewhat longer than in [Zn(male)(H2O)(phen)]n [2.1295 (17) and 2.1741 (19) Å; male is maleate; Li et al., 2005].

As shown in Fig. 2, the molecular packing of (I) exhibits a three-dimensional supramolecular structure in which both hydrogen-bonding and π–π stacking interactions play an important role. The complex molecules are linked to one another through hydrogen bonds between coordinated water molecules and the uncoordinated carboxylate O atoms of neighboring molecules to form layers in the crystal structure (Table 2). Neighboring layers are linked to each other through π–π stacking interactions between the phen rings of adjacent molecules, characterized by interplanar distances in the range 3.446 (14) to 3.542 (14) Å.

Experimental top

ZnO (0.162 g, 2 mmol) was added slowly to an aqueous solution (15 ml) of malonic acid (0.104 g, 1 mmol). The reaction mixture was stirred for one hour at 353 K, and then an ethanol solution (5 ml) of 1,10-phenanthroline (0.198 g, 1 mmol) was added with continuous stirring. After half an hour, the reaction mixture was cooled to room temperature and filtered. Colorless single crystals were obtained from the filtrate after two weeks.

Refinement top

The water H atoms were located in a difference Fourier map and their positional parameters were refined freely [or with O—H distances restrained to 0.XX (s.u.) Å?]; their Uiso(H) values were fixed at 0.063 Å2. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H bond lengths of 0.93 or 0.97 Å [Uiso(H) = 1.2Ueq(C)].

Structure description top

There has been considerable interest in the design and synthesis of transition metal complexes with carboxylate ligands in coordination chemistry, as a result of the fact that this type of complex has potential application in molecular-based magnets, catalysis, supramolecular chemistry and biological systems (Li et al., 2002; Shi et al., 2000; Devereux et al., 2000). As an important dicarboxylate ligand, the malonate dianion may acts in a chelating bidentate manner and adopt different carboxylate bridging coordination modes, such as syn/syn, syn/anti and anti/anti (Li et al., 1997; Lightfoot et al.,1999; Lis et al., 1979; Muro et al., 1998). ZnII complexes with the malonate ligand have potential applications in modified metalloenzymes and in precursor systems for Zn-containing ceramic materials. Serval structures of ZnII complexes with malonate (mal) have been reported, viz. {Na2[Zn(mal)2·2H2O}n (Lin et al., 2003), Zn2(mal)2(pym)(H2O)]n.nH2O (pym is pyrimidine; Delgado et al., 2003) and [Zn2(H2O)2(mal)2(C4H4N2)] (Zhang et al., 2003). These structures were all found to be polymeric, with the malonate ligands serving as bridges. To the best of our knowledge, no mononuclear ZnII complexes with the malonate ligand in which malonate acts as a dicarboxylate chelating ligand have been reported. We report here the crystal structure of one such complex, diaquamalonato(1,10-phenanthroline)zinc(II), (I), with a dicaboxylate chelating malonate ligand.

The molecular structure of (I), shown in Fig. 1, consists of discrete monomers. A malonate dianion chelates the ZnII atom through two O atoms from different carboxylate groups. The ZnII atom is also coordinated by the two 1,10-phenanthroline N atoms and two O atoms of two cis water molecules. Each malonate ligand forms a six-membered chelate ring with one ZnII ion in a boat-type configuration; the malonate ligand acts only as a chelating ligand and does not act as a bridge between metal atoms. The carboxylate chelating coordination mode is similar to those of [Mn(mal)(bipy)(H2O)2] (bipy is 2,2'-bipyridine; Sain et al., 2003) and [Mn(mal)(phen)(H2O)2] (phen is 1,10-phenanthroline; Zhang et al.,2004). The ZnII atom exhibits a distorted octahedral coordination sphere with the bond angles ranging from 166.21 (6) to 172.07 (6)° for trans angles and from 77.05 (6) to 99.19 (6)° for the other bond angles (Table 1). The Zn—O(carboxylate) bond distances are 2.0618 (13) and 2.0646 (15) Å. In [Zn2(H2O)2(mal)2(C4H4N2)] (Zhang et al., 2003), the corresponding Zn—O(carboxylate) bond distances are 2.085 (2) and 2.082 (3) Å; the difference is probably due to the effect of the chelating coordination in (I). The Zn—O(water) distances of 2.1152 (17) and 2.1364 (16) Å are comparable to those found in [Zn2(mal)2(pym)(H2O)]n.nH2O [2.175 (4) Å; Delgado et al., 2003]. The Zn—N bond lengths are 2.1601 (17) and 2.1745 (17) Å, somewhat longer than in [Zn(male)(H2O)(phen)]n [2.1295 (17) and 2.1741 (19) Å; male is maleate; Li et al., 2005].

As shown in Fig. 2, the molecular packing of (I) exhibits a three-dimensional supramolecular structure in which both hydrogen-bonding and π–π stacking interactions play an important role. The complex molecules are linked to one another through hydrogen bonds between coordinated water molecules and the uncoordinated carboxylate O atoms of neighboring molecules to form layers in the crystal structure (Table 2). Neighboring layers are linked to each other through π–π stacking interactions between the phen rings of adjacent molecules, characterized by interplanar distances in the range 3.446 (14) to 3.542 (14) Å.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. A view of part of the infinite two-dimensional supramolecular structure of complex (I), showing hydrogen-bonding interactions (dashed lines) in the ab plane (phen moieties are not shown for clarity).
[Figure 3] Fig. 3. The molecular packing of (I), with hydrogen bonds shown as dashed lines (H atoms without H-bonding interacting are not shown).
Diaquamalonato(1,10-phenanthroline)zinc(II) top
Crystal data top
[Zn(C3H2O4)(C12H8N2)(H2O)2]F(000) = 784
Mr = 383.65Dx = 1.712 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 3676 reflections
a = 10.3369 (11) Åθ = 0.0–0.0°
b = 9.6662 (10) ŵ = 1.69 mm−1
c = 15.4737 (16) ÅT = 292 K
β = 105.720 (2)°Prism, colorless
V = 1488.3 (3) Å30.27 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3237 independent reflections
Radiation source: fine-focus sealed tube2572 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
φ and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −13→11
Tmin = 0.659, Tmax = 0.751k = −12→12
10345 measured reflectionsl = −16→19
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0343P)2]
where P = (Fo2 + 2Fc2)/3
3237 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.34 e Å−3
4 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Zn(C3H2O4)(C12H8N2)(H2O)2]V = 1488.3 (3) Å3
Mr = 383.65Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3369 (11) ŵ = 1.69 mm−1
b = 9.6662 (10) ÅT = 292 K
c = 15.4737 (16) Å0.27 × 0.20 × 0.18 mm
β = 105.720 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3237 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2572 reflections with I > 2σ(I)
Tmin = 0.659, Tmax = 0.751Rint = 0.063
10345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0334 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.34 e Å−3
3237 reflectionsΔρmin = −0.35 e Å−3
229 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
xyzUiso*/Ueq
Zn10.65669 (2)0.39602 (2)0.231105 (16)0.02812 (9)
N10.85172 (17)0.30751 (18)0.29292 (12)0.0325 (4)
N20.77262 (18)0.57322 (17)0.29610 (12)0.0318 (4)
O10.58103 (15)0.20512 (13)0.18325 (9)0.0325 (3)
O20.45738 (19)0.07241 (16)0.07647 (11)0.0542 (5)
O30.69264 (15)0.43374 (14)0.10833 (10)0.0354 (4)
O40.67092 (16)0.38067 (14)−0.03373 (10)0.0364 (4)
O50.47378 (17)0.51175 (16)0.19912 (11)0.0369 (4)
O60.59419 (18)0.34566 (16)0.34661 (11)0.0412 (4)
C10.8894 (2)0.1768 (2)0.29118 (16)0.0407 (6)
H10.82770.11350.25820.049*
C21.0172 (3)0.1296 (2)0.33640 (18)0.0475 (6)
H21.03930.03670.33420.057*
C31.1088 (3)0.2207 (3)0.38359 (17)0.0516 (7)
H31.19480.19080.41340.062*
C41.0738 (2)0.3609 (3)0.38763 (16)0.0435 (6)
C51.1630 (3)0.4627 (3)0.43670 (18)0.0579 (8)
H5A1.25090.43820.46620.069*
C61.1225 (3)0.5936 (3)0.44109 (18)0.0565 (8)
H6A1.18220.65760.47520.068*
C70.9892 (3)0.6375 (2)0.39439 (16)0.0429 (6)
C80.9427 (3)0.7729 (3)0.39614 (18)0.0544 (7)
H80.99830.84020.43010.065*
C90.8159 (3)0.8056 (2)0.34798 (19)0.0537 (7)
H90.78430.89560.34840.064*
C110.8991 (2)0.5405 (2)0.34368 (14)0.0315 (5)
C120.9429 (2)0.3990 (2)0.34160 (14)0.0322 (5)
C150.5161 (2)0.1810 (2)0.10202 (14)0.0302 (5)
C140.5049 (2)0.2940 (2)0.03250 (14)0.0320 (5)
H14A0.43650.35900.03890.038*
H14B0.47350.2524−0.02650.038*
C130.6321 (2)0.37496 (18)0.03583 (14)0.0283 (5)
C100.7332 (2)0.7033 (2)0.29772 (17)0.0419 (6)
H100.64720.72750.26410.050*
H5B0.455 (3)0.561 (3)0.2392 (18)0.063*
H5C0.443 (3)0.545 (3)0.1521 (17)0.063*
H6B0.619 (3)0.281 (3)0.3766 (18)0.063*
H6C0.579 (3)0.416 (2)0.3707 (19)0.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03131 (16)0.02779 (13)0.02259 (15)−0.00289 (10)0.00273 (10)−0.00065 (10)
N10.0352 (11)0.0347 (10)0.0265 (10)0.0030 (8)0.0067 (8)−0.0020 (8)
N20.0328 (11)0.0322 (9)0.0310 (11)−0.0033 (7)0.0097 (8)−0.0003 (8)
O10.0413 (9)0.0293 (7)0.0235 (8)−0.0075 (6)0.0031 (7)−0.0003 (6)
O20.0757 (14)0.0423 (9)0.0377 (10)−0.0285 (8)0.0036 (9)−0.0031 (7)
O30.0437 (10)0.0373 (8)0.0245 (8)−0.0135 (7)0.0081 (7)−0.0022 (6)
O40.0448 (10)0.0409 (8)0.0243 (8)−0.0040 (7)0.0105 (7)0.0015 (6)
O50.0421 (10)0.0398 (9)0.0247 (9)0.0103 (7)0.0018 (8)−0.0001 (7)
O60.0637 (12)0.0314 (8)0.0314 (10)0.0054 (8)0.0176 (8)0.0038 (7)
C10.0486 (15)0.0373 (13)0.0356 (14)0.0054 (11)0.0104 (11)0.0013 (10)
C20.0529 (17)0.0465 (14)0.0457 (16)0.0177 (12)0.0181 (13)0.0099 (12)
C30.0375 (15)0.0722 (18)0.0448 (16)0.0168 (13)0.0106 (12)0.0183 (14)
C40.0331 (14)0.0605 (15)0.0343 (14)−0.0005 (11)0.0049 (11)0.0063 (11)
C50.0339 (15)0.081 (2)0.0483 (17)−0.0087 (14)−0.0062 (13)0.0114 (15)
C60.0438 (16)0.0748 (19)0.0409 (16)−0.0271 (14)−0.0054 (12)0.0019 (14)
C70.0449 (15)0.0490 (14)0.0321 (14)−0.0167 (11)0.0058 (11)−0.0025 (11)
C80.068 (2)0.0445 (14)0.0498 (17)−0.0267 (13)0.0142 (15)−0.0112 (12)
C90.0669 (19)0.0307 (12)0.0674 (19)−0.0090 (12)0.0246 (16)−0.0058 (12)
C110.0333 (13)0.0387 (11)0.0224 (11)−0.0078 (10)0.0072 (10)−0.0002 (9)
C120.0312 (12)0.0426 (12)0.0222 (11)−0.0008 (10)0.0062 (9)0.0009 (9)
C150.0314 (12)0.0308 (11)0.0289 (12)−0.0026 (9)0.0088 (9)−0.0014 (9)
C140.0303 (12)0.0375 (11)0.0237 (11)−0.0010 (9)0.0001 (9)−0.0009 (9)
C130.0330 (12)0.0241 (10)0.0258 (12)0.0039 (8)0.0048 (9)0.0049 (8)
C100.0422 (14)0.0360 (12)0.0502 (16)−0.0018 (10)0.0171 (12)−0.0004 (11)
Geometric parameters (Å, º) top
Zn1—O12.0618 (13)C2—H20.9300
Zn1—O32.0646 (15)C3—C41.408 (3)
Zn1—O62.1152 (17)C3—H30.9300
Zn1—O52.1364 (16)C4—C121.397 (3)
Zn1—N12.1601 (17)C4—C51.420 (4)
Zn1—N22.1745 (17)C5—C61.340 (4)
N1—C11.325 (3)C5—H5A0.9300
N1—C121.362 (3)C6—C71.436 (4)
N2—C101.324 (3)C6—H6A0.9300
N2—C111.353 (3)C7—C81.397 (3)
O1—C151.276 (2)C7—C111.402 (3)
O2—C151.224 (2)C8—C91.358 (4)
O3—C131.262 (2)C8—H80.9300
O4—C131.248 (3)C9—C101.398 (3)
O5—H5B0.85 (2)C9—H90.9300
O5—H5C0.78 (2)C11—C121.443 (3)
O6—H6B0.78 (2)C15—C141.515 (3)
O6—H6C0.81 (2)C14—C131.518 (3)
C1—C21.393 (3)C14—H14A0.9700
C1—H10.9300C14—H14B0.9700
C2—C31.353 (4)C10—H100.9300
O1—Zn1—O388.45 (6)C12—C4—C5119.2 (2)
O1—Zn1—O685.67 (6)C3—C4—C5123.6 (2)
O3—Zn1—O6172.07 (6)C6—C5—C4121.0 (2)
O1—Zn1—O599.19 (6)C6—C5—H5A119.5
O3—Zn1—O593.61 (6)C4—C5—H5A119.5
O6—Zn1—O582.10 (7)C5—C6—C7121.6 (2)
O1—Zn1—N191.27 (6)C5—C6—H6A119.2
O3—Zn1—N195.64 (6)C7—C6—H6A119.2
O6—Zn1—N189.82 (7)C8—C7—C11117.2 (2)
O5—Zn1—N1166.21 (6)C8—C7—C6123.7 (2)
O1—Zn1—N2168.23 (6)C11—C7—C6119.0 (2)
O3—Zn1—N294.15 (6)C9—C8—C7119.6 (2)
O6—Zn1—N292.68 (7)C9—C8—H8120.2
O5—Zn1—N292.11 (6)C7—C8—H8120.2
N1—Zn1—N277.05 (6)C8—C9—C10119.7 (2)
C1—N1—C12117.87 (19)C8—C9—H9120.2
C1—N1—Zn1127.83 (15)C10—C9—H9120.2
C12—N1—Zn1114.26 (14)N2—C11—C7123.0 (2)
C10—N2—C11117.97 (19)N2—C11—C12118.20 (18)
C10—N2—Zn1128.53 (16)C7—C11—C12118.8 (2)
C11—N2—Zn1113.42 (13)N1—C12—C4122.7 (2)
C15—O1—Zn1124.35 (12)N1—C12—C11116.95 (19)
C13—O3—Zn1124.66 (13)C4—C12—C11120.3 (2)
Zn1—O5—H5B119.5 (19)O2—C15—O1123.87 (19)
Zn1—O5—H5C123 (2)O2—C15—C14116.95 (19)
H5B—O5—H5C110 (3)O1—C15—C14119.13 (17)
Zn1—O6—H6B124 (2)C15—C14—C13116.62 (17)
Zn1—O6—H6C110 (2)C15—C14—H14A108.1
H6B—O6—H6C118 (3)C13—C14—H14A108.1
N1—C1—C2123.1 (2)C15—C14—H14B108.1
N1—C1—H1118.4C13—C14—H14B108.1
C2—C1—H1118.4H14A—C14—H14B107.3
C3—C2—C1119.2 (2)O4—C13—O3123.3 (2)
C3—C2—H2120.4O4—C13—C14118.13 (18)
C1—C2—H2120.4O3—C13—C14118.59 (19)
C2—C3—C4120.0 (2)N2—C10—C9122.5 (2)
C2—C3—H3120.0N2—C10—H10118.7
C4—C3—H3120.0C9—C10—H10118.8
C12—C4—C3117.2 (2)
O1—Zn1—N1—C11.33 (19)C4—C5—C6—C7−1.9 (5)
O3—Zn1—N1—C1−87.24 (19)C5—C6—C7—C8−179.4 (3)
O6—Zn1—N1—C186.99 (19)C5—C6—C7—C110.6 (4)
O5—Zn1—N1—C1140.9 (3)C11—C7—C8—C9−1.6 (4)
N2—Zn1—N1—C1179.8 (2)C6—C7—C8—C9178.3 (3)
O1—Zn1—N1—C12−176.14 (15)C7—C8—C9—C100.4 (4)
O3—Zn1—N1—C1295.29 (15)C10—N2—C11—C70.2 (3)
O6—Zn1—N1—C12−90.48 (16)Zn1—N2—C11—C7−176.91 (18)
O5—Zn1—N1—C12−36.6 (4)C10—N2—C11—C12−179.5 (2)
N2—Zn1—N1—C122.31 (15)Zn1—N2—C11—C123.4 (2)
O1—Zn1—N2—C10−172.2 (3)C8—C7—C11—N21.3 (4)
O3—Zn1—N2—C1085.4 (2)C6—C7—C11—N2−178.6 (2)
O6—Zn1—N2—C10−90.5 (2)C8—C7—C11—C12−178.9 (2)
O5—Zn1—N2—C10−8.4 (2)C6—C7—C11—C121.1 (3)
N1—Zn1—N2—C10−179.7 (2)C1—N1—C12—C41.3 (3)
O1—Zn1—N2—C114.6 (4)Zn1—N1—C12—C4179.01 (18)
O3—Zn1—N2—C11−97.86 (15)C1—N1—C12—C11−179.1 (2)
O6—Zn1—N2—C1186.18 (15)Zn1—N1—C12—C11−1.3 (3)
O5—Zn1—N2—C11168.37 (15)C3—C4—C12—N1−1.3 (4)
N1—Zn1—N2—C11−3.01 (14)C5—C4—C12—N1179.8 (2)
O3—Zn1—O1—C15−34.34 (16)C3—C4—C12—C11179.1 (2)
O6—Zn1—O1—C15140.33 (17)C5—C4—C12—C110.2 (4)
O5—Zn1—O1—C1559.06 (17)N2—C11—C12—N1−1.4 (3)
N1—Zn1—O1—C15−129.95 (17)C7—C11—C12—N1178.9 (2)
N2—Zn1—O1—C15−137.3 (3)N2—C11—C12—C4178.2 (2)
O1—Zn1—O3—C1323.27 (16)C7—C11—C12—C4−1.5 (3)
O6—Zn1—O3—C13−18.9 (5)Zn1—O1—C15—O2−170.56 (18)
O5—Zn1—O3—C13−75.84 (17)Zn1—O1—C15—C146.8 (3)
N1—Zn1—O3—C13114.40 (17)O2—C15—C14—C13−138.8 (2)
N2—Zn1—O3—C13−168.22 (16)O1—C15—C14—C1343.7 (3)
C12—N1—C1—C2−0.2 (3)Zn1—O3—C13—O4−166.87 (14)
Zn1—N1—C1—C2−177.55 (18)Zn1—O3—C13—C1413.6 (3)
N1—C1—C2—C3−0.9 (4)C15—C14—C13—O4125.0 (2)
C1—C2—C3—C40.9 (4)C15—C14—C13—O3−55.5 (3)
C2—C3—C4—C120.1 (4)C11—N2—C10—C9−1.5 (3)
C2—C3—C4—C5179.0 (3)Zn1—N2—C10—C9175.11 (18)
C12—C4—C5—C61.5 (4)C8—C9—C10—N21.2 (4)
C3—C4—C5—C6−177.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5B···O1i0.85 (2)1.94 (2)2.772 (2)168 (3)
O6—H6B···O4ii0.78 (2)2.06 (2)2.837 (2)173 (3)
O5—H5C···O4iii0.78 (2)2.02 (2)2.792 (2)169 (3)
O6—H6C···O2i0.81 (2)1.81 (2)2.617 (2)179 (3)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Zn(C3H2O4)(C12H8N2)(H2O)2]
Mr383.65
Crystal system, space groupMonoclinic, P21/c
Temperature (K)292
a, b, c (Å)10.3369 (11), 9.6662 (10), 15.4737 (16)
β (°) 105.720 (2)
V (Å3)1488.3 (3)
Z4
Radiation typeMo Kα
µ (mm−1)1.69
Crystal size (mm)0.27 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.659, 0.751
No. of measured, independent and
observed [I > 2σ(I)] reflections		10345, 3237, 2572
Rint0.063
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.071, 0.95
No. of reflections3237
No. of parameters229
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.34, −0.35

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Zn1—O12.0618 (13)Zn1—N22.1745 (17)
Zn1—O32.0646 (15)O1—C151.276 (2)
Zn1—O62.1152 (17)O2—C151.224 (2)
Zn1—O52.1364 (16)O3—C131.262 (2)
Zn1—N12.1601 (17)O4—C131.248 (3)
O1—Zn1—O388.45 (6)O6—Zn1—N189.82 (7)
O1—Zn1—O685.67 (6)O5—Zn1—N1166.21 (6)
O3—Zn1—O6172.07 (6)O1—Zn1—N2168.23 (6)
O1—Zn1—O599.19 (6)O3—Zn1—N294.15 (6)
O3—Zn1—O593.61 (6)O6—Zn1—N292.68 (7)
O6—Zn1—O582.10 (7)O5—Zn1—N292.11 (6)
O1—Zn1—N191.27 (6)N1—Zn1—N277.05 (6)
O3—Zn1—N195.64 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5B···O1i0.85 (2)1.94 (2)2.772 (2)168 (3)
O6—H6B···O4ii0.78 (2)2.06 (2)2.837 (2)173 (3)
O5—H5C···O4iii0.78 (2)2.02 (2)2.792 (2)169 (3)
O6—H6C···O2i0.81 (2)1.81 (2)2.617 (2)179 (3)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z.
 

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