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In the title complex, [Zn(C7H4ClO3)2(C12H8N2)(H2O)], the Zn atom is coordinated by two 5-chloro­salicylate anions, one 1,10-phenanthroline mol­ecule and one water mol­ecule, displaying a distorted trigonal–bipyramidal geometry. The crystal structure is stabilized by intra- and inter­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040937/om2150sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040937/om2150Isup2.hkl
Contains datablock I

CCDC reference: 660157

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.084
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

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Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.854(10) ...... 3.00 su-Ra O6 -H6A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O6 -H6A 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.92 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

A lot of attention has been paid to the metal salicylate owing to their intriguing structural features (Brownless et al., 1999; Lemoine et al., 2002; Zhu et al., 2003; Yin et al., 2004; Wen et al., 2007a,b,c) and biological applications (Lemoine et al., 2004). We report here the structure of a Zn (II) complex with 5-chloroosalicylate ligand (Melnik et al., 2001). The title complex, Zn(C7H4ClO3)2(C12H8N2)(H2O) was synthesized under hydrothermal conditions. The Zn atom is coordinated in a distorted trigonal bipyramid geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from one 1,10-phenanthroline and one water O atom (Fig. 1). One Zn—N bond is significantly shorter than the other (Zn1—N1 = 2.099 (2) Å, Zn1—N2 = 2.160 (2) Å). These distances are comparable to the Zn—N bond lengths (Zn—N1 = 2.109 (3) Å, Zn—N2 = 2.178 (3) Å) in [Zn(ta)(phen)(H2O)]n (Sun et al., 2001). The complex has rich hydrogen bonds formed by the coordinated water molecule, hydroxy and carboxyl O atoms (Fig. 2). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds interactions (Fig. 3).

Related literature top

For related literature, see: Brownless et al. (1999); Lemoine et al. (2002, 2004); Melnik et al. (2001); Sun et al. (2001); Wen et al. (2007a,b,c); Yin et al. (2004); Zhu et al. (2003).

Experimental top

A mixture of Zn(NO3)2.6H2O (0.1 mmol), phen (0.1 mmol), 5-chlorosalicylic acid (0.2 mmol) and distilled water (10 ml) was put into a Teflon-lined autoclave (20 ml) and then heated at 413 K for 72 h. Colorless block-like crystals suitable for X-ray analysis were collected from the reaction mixture.

Refinement top

The aromatic H atoms were positioned geometrically and were included in the refinement in the riding-model approximation [C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C)]. The water H atoms were found in a difference Fourier map and were refined with distance restraints of O—H = 0.85 (1)Å and Uiso(H) = 1.2 Ueq(O).

Structure description top

A lot of attention has been paid to the metal salicylate owing to their intriguing structural features (Brownless et al., 1999; Lemoine et al., 2002; Zhu et al., 2003; Yin et al., 2004; Wen et al., 2007a,b,c) and biological applications (Lemoine et al., 2004). We report here the structure of a Zn (II) complex with 5-chloroosalicylate ligand (Melnik et al., 2001). The title complex, Zn(C7H4ClO3)2(C12H8N2)(H2O) was synthesized under hydrothermal conditions. The Zn atom is coordinated in a distorted trigonal bipyramid geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from one 1,10-phenanthroline and one water O atom (Fig. 1). One Zn—N bond is significantly shorter than the other (Zn1—N1 = 2.099 (2) Å, Zn1—N2 = 2.160 (2) Å). These distances are comparable to the Zn—N bond lengths (Zn—N1 = 2.109 (3) Å, Zn—N2 = 2.178 (3) Å) in [Zn(ta)(phen)(H2O)]n (Sun et al., 2001). The complex has rich hydrogen bonds formed by the coordinated water molecule, hydroxy and carboxyl O atoms (Fig. 2). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds interactions (Fig. 3).

For related literature, see: Brownless et al. (1999); Lemoine et al. (2002, 2004); Melnik et al. (2001); Sun et al. (2001); Wen et al. (2007a,b,c); Yin et al. (2004); Zhu et al. (2003).

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title complex with 30% probability ellipsoids.
[Figure 2] Fig. 2. Representation of hydrogen bonds (dashed lines) observed in the title compound.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed down the a axis. Hydrogen bonds are represented by dashed lines.
Aquabis(5-chlorosalicylato-κO)(1,10-phenanthroline-κ2N,N')zinc(II) top
Crystal data top
[Zn(C7H4ClO3)2(C12H8N2)(H2O)]Z = 2
Mr = 606.69F(000) = 616
Triclinic, P1Dx = 1.644 Mg m3
a = 8.681 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.777 (6) ÅCell parameters from 5553 reflections
c = 12.982 (9) Åθ = 3.2–27.5°
α = 72.06 (2)°µ = 1.27 mm1
β = 76.98 (2)°T = 293 K
γ = 81.592 (19)°Block, colourless
V = 1225.9 (12) Å30.28 × 0.26 × 0.25 mm
Data collection top
Rigaku R-AXIS RAPID Weissenberg IP
diffractometer
4462 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
ω scansh = 119
12131 measured reflectionsk = 1514
5553 independent reflectionsl = 1616
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0162P)2 + 0.2964P]
where P = (Fo2 + 2Fc2)/3
5553 reflections(Δ/σ)max = 0.002
355 parametersΔρmax = 0.54 e Å3
4 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Zn(C7H4ClO3)2(C12H8N2)(H2O)]γ = 81.592 (19)°
Mr = 606.69V = 1225.9 (12) Å3
Triclinic, P1Z = 2
a = 8.681 (4) ÅMo Kα radiation
b = 11.777 (6) ŵ = 1.27 mm1
c = 12.982 (9) ÅT = 293 K
α = 72.06 (2)°0.28 × 0.26 × 0.25 mm
β = 76.98 (2)°
Data collection top
Rigaku R-AXIS RAPID Weissenberg IP
diffractometer
4462 reflections with I > 2σ(I)
12131 measured reflectionsRint = 0.049
5553 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0374 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.54 e Å3
5553 reflectionsΔρmin = 0.44 e Å3
355 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
Zn10.64074 (3)0.98442 (2)0.813250 (19)0.03415 (9)
N10.5901 (2)1.07549 (15)0.65649 (14)0.0353 (4)
N20.8038 (2)0.88896 (14)0.71017 (14)0.0333 (4)
O10.7926 (2)1.09096 (14)0.81791 (15)0.0494 (4)
O20.7919 (2)1.05973 (15)0.99631 (15)0.0510 (4)
O30.9882 (2)1.15930 (17)1.05330 (15)0.0578 (5)
H3A0.917 (2)1.115 (2)1.058 (3)0.069*
O40.57974 (18)0.83560 (12)0.93499 (11)0.0373 (3)
O50.4509 (2)0.80266 (16)0.81983 (14)0.0563 (5)
O60.2744 (3)0.6264 (2)0.8834 (2)0.0726 (6)
H6A0.317 (4)0.6903 (18)0.843 (3)0.087*
C10.9516 (2)1.20453 (18)0.86614 (18)0.0348 (5)
C21.0224 (3)1.2225 (2)0.9464 (2)0.0418 (5)
C31.1299 (3)1.3083 (2)0.9158 (2)0.0527 (6)
H31.17881.31860.96880.063*
C41.1657 (3)1.3782 (2)0.8093 (3)0.0540 (7)
H41.23801.43580.79000.065*
C51.0934 (3)1.3625 (2)0.7307 (2)0.0423 (5)
C60.9881 (3)1.27671 (19)0.75859 (19)0.0385 (5)
H60.94071.26690.70470.046*
C70.8372 (2)1.11091 (19)0.8966 (2)0.0380 (5)
C80.4146 (2)0.67431 (18)1.00260 (18)0.0359 (5)
C90.3112 (3)0.6059 (2)0.9838 (2)0.0502 (6)
C100.2413 (3)0.5146 (2)1.0708 (3)0.0643 (8)
H100.17180.46931.05860.077*
C110.2734 (3)0.4907 (2)1.1739 (3)0.0660 (9)
H110.22610.42931.23150.079*
C120.3758 (3)0.5577 (2)1.1922 (2)0.0522 (7)
C130.4467 (3)0.64840 (19)1.10822 (18)0.0400 (5)
H130.51640.69261.12180.048*
C140.4861 (2)0.77654 (18)0.91259 (17)0.0356 (5)
C150.4887 (3)1.1706 (2)0.63063 (19)0.0463 (6)
H150.42871.20090.68680.056*
C160.4683 (3)1.2270 (2)0.5230 (2)0.0529 (6)
H160.39681.29420.50800.064*
C170.5538 (3)1.1834 (2)0.4396 (2)0.0501 (6)
H170.53981.21960.36740.060*
C180.6633 (3)1.0831 (2)0.46356 (18)0.0400 (5)
C190.7607 (3)1.0325 (2)0.38123 (19)0.0489 (6)
H190.75081.06550.30780.059*
C200.8664 (3)0.9377 (2)0.40863 (19)0.0497 (6)
H200.92880.90680.35360.060*
C210.8846 (3)0.8841 (2)0.52007 (18)0.0403 (5)
C220.9915 (3)0.7849 (2)0.5542 (2)0.0495 (6)
H221.05340.74830.50300.059*
C231.0045 (3)0.7421 (2)0.6625 (2)0.0481 (6)
H231.07620.67710.68540.058*
C240.9086 (3)0.79723 (19)0.73877 (19)0.0408 (5)
H240.91900.76830.81230.049*
C250.7908 (2)0.93152 (17)0.60344 (17)0.0324 (4)
C260.6781 (2)1.03261 (18)0.57349 (17)0.0331 (4)
Cl11.13591 (10)1.45253 (6)0.59530 (6)0.0686 (2)
Cl20.41211 (12)0.52968 (9)1.32473 (7)0.0937 (3)
O70.4401 (2)1.07947 (14)0.88416 (13)0.0429 (4)
H7B0.364 (2)1.0363 (18)0.915 (2)0.051*
H7A0.455 (3)1.108 (2)0.9330 (17)0.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04762 (15)0.03512 (13)0.01979 (12)0.01181 (11)0.00212 (10)0.00721 (9)
N10.0421 (9)0.0392 (9)0.0238 (9)0.0076 (9)0.0023 (7)0.0088 (7)
N20.0397 (9)0.0355 (9)0.0251 (9)0.0125 (8)0.0022 (7)0.0080 (7)
O10.0595 (10)0.0475 (9)0.0518 (11)0.0156 (8)0.0167 (8)0.0198 (8)
O20.0553 (10)0.0515 (9)0.0451 (11)0.0131 (8)0.0009 (8)0.0158 (8)
O30.0748 (13)0.0657 (11)0.0397 (10)0.0093 (10)0.0192 (9)0.0176 (9)
O40.0483 (8)0.0349 (7)0.0252 (8)0.0110 (7)0.0010 (6)0.0045 (6)
O50.0710 (11)0.0678 (11)0.0312 (9)0.0140 (10)0.0138 (8)0.0091 (8)
O60.0778 (14)0.0823 (14)0.0773 (17)0.0227 (12)0.0165 (12)0.0426 (13)
C10.0333 (10)0.0362 (10)0.0398 (12)0.0021 (10)0.0085 (9)0.0189 (9)
C20.0433 (12)0.0470 (12)0.0422 (13)0.0039 (11)0.0148 (10)0.0214 (10)
C30.0488 (13)0.0626 (15)0.0601 (18)0.0070 (13)0.0238 (13)0.0262 (13)
C40.0394 (12)0.0540 (15)0.075 (2)0.0095 (12)0.0121 (13)0.0238 (14)
C50.0390 (11)0.0421 (11)0.0443 (14)0.0016 (11)0.0036 (10)0.0140 (10)
C60.0407 (11)0.0408 (11)0.0390 (13)0.0030 (10)0.0111 (10)0.0191 (9)
C70.0369 (11)0.0359 (11)0.0447 (13)0.0020 (10)0.0072 (10)0.0193 (10)
C80.0355 (10)0.0312 (10)0.0383 (12)0.0037 (9)0.0003 (9)0.0108 (9)
C90.0462 (13)0.0470 (13)0.0644 (18)0.0048 (12)0.0034 (12)0.0308 (12)
C100.0592 (16)0.0442 (14)0.092 (2)0.0211 (13)0.0075 (16)0.0305 (15)
C110.0615 (17)0.0361 (12)0.080 (2)0.0152 (13)0.0175 (16)0.0048 (13)
C120.0478 (13)0.0418 (12)0.0498 (16)0.0025 (12)0.0020 (12)0.0030 (11)
C130.0378 (11)0.0344 (10)0.0391 (13)0.0056 (10)0.0013 (10)0.0010 (9)
C140.0403 (11)0.0352 (10)0.0278 (11)0.0007 (10)0.0006 (9)0.0101 (8)
C150.0538 (14)0.0479 (13)0.0333 (13)0.0008 (12)0.0040 (11)0.0106 (10)
C160.0602 (15)0.0522 (13)0.0382 (14)0.0050 (13)0.0103 (12)0.0049 (11)
C170.0609 (15)0.0576 (14)0.0280 (12)0.0115 (13)0.0120 (11)0.0013 (10)
C180.0502 (12)0.0466 (12)0.0243 (11)0.0162 (11)0.0030 (9)0.0090 (9)
C190.0664 (15)0.0598 (14)0.0225 (11)0.0184 (14)0.0031 (11)0.0123 (10)
C200.0644 (15)0.0596 (14)0.0286 (12)0.0140 (14)0.0037 (11)0.0228 (11)
C210.0490 (12)0.0443 (12)0.0314 (12)0.0130 (11)0.0007 (10)0.0179 (9)
C220.0536 (14)0.0497 (13)0.0484 (15)0.0070 (12)0.0026 (12)0.0265 (11)
C230.0503 (13)0.0420 (12)0.0535 (16)0.0020 (12)0.0094 (12)0.0170 (11)
C240.0477 (12)0.0376 (11)0.0373 (13)0.0105 (11)0.0076 (10)0.0081 (9)
C250.0376 (10)0.0357 (10)0.0261 (10)0.0160 (9)0.0004 (8)0.0110 (8)
C260.0401 (11)0.0382 (10)0.0228 (10)0.0163 (10)0.0012 (8)0.0089 (8)
Cl10.0842 (5)0.0558 (4)0.0535 (4)0.0097 (4)0.0007 (4)0.0062 (3)
Cl20.1015 (6)0.1024 (6)0.0450 (4)0.0271 (5)0.0060 (4)0.0281 (4)
O70.0572 (10)0.0429 (8)0.0263 (8)0.0089 (8)0.0018 (7)0.0116 (6)
Geometric parameters (Å, º) top
Zn1—O11.9706 (18)C9—C101.390 (4)
Zn1—O42.0094 (17)C10—C111.364 (5)
Zn1—N12.099 (2)C10—H100.9300
Zn1—O72.1154 (17)C11—C121.373 (4)
Zn1—N22.1599 (18)C11—H110.9300
N1—C151.325 (3)C12—C131.372 (3)
N1—C261.361 (3)C12—Cl21.741 (3)
N2—C241.323 (3)C13—H130.9300
N2—C251.345 (3)C15—C161.389 (3)
O1—C71.265 (3)C15—H150.9300
O2—C71.247 (3)C16—C171.363 (3)
O3—C21.346 (3)C16—H160.9300
O3—H3A0.847 (10)C17—C181.404 (3)
O4—C141.275 (3)C17—H170.9300
O5—C141.244 (3)C18—C261.395 (3)
O6—C91.354 (4)C18—C191.432 (3)
O6—H6A0.854 (10)C19—C201.348 (3)
C1—C61.386 (3)C19—H190.9300
C1—C21.404 (3)C20—C211.424 (3)
C1—C71.494 (3)C20—H200.9300
C2—C31.383 (4)C21—C221.404 (3)
C3—C41.366 (4)C21—C251.410 (3)
C3—H30.9300C22—C231.365 (4)
C4—C51.382 (4)C22—H220.9300
C4—H40.9300C23—C241.400 (3)
C5—C61.372 (3)C23—H230.9300
C5—Cl11.738 (3)C24—H240.9300
C6—H60.9300C25—C261.439 (3)
C8—C131.393 (3)O7—H7B0.844 (10)
C8—C91.395 (3)O7—H7A0.847 (10)
C8—C141.492 (3)
O1—Zn1—O4123.68 (8)C10—C11—H11120.2
O1—Zn1—N198.46 (8)C12—C11—H11120.2
O4—Zn1—N1137.84 (7)C13—C12—C11121.0 (3)
O1—Zn1—O794.31 (8)C13—C12—Cl2119.5 (2)
O4—Zn1—O788.75 (7)C11—C12—Cl2119.5 (2)
N1—Zn1—O789.25 (7)C12—C13—C8120.1 (2)
O1—Zn1—N296.73 (8)C12—C13—H13120.0
O4—Zn1—N294.37 (7)C8—C13—H13120.0
N1—Zn1—N278.09 (8)O5—C14—O4122.4 (2)
O7—Zn1—N2164.28 (7)O5—C14—C8119.6 (2)
C15—N1—C26118.14 (19)O4—C14—C8117.99 (19)
C15—N1—Zn1127.30 (15)N1—C15—C16122.7 (2)
C26—N1—Zn1114.49 (14)N1—C15—H15118.6
C24—N2—C25118.49 (18)C16—C15—H15118.6
C24—N2—Zn1128.86 (15)C17—C16—C15119.6 (2)
C25—N2—Zn1112.65 (13)C17—C16—H16120.2
C7—O1—Zn1132.72 (17)C15—C16—H16120.2
C2—O3—H3A106 (2)C16—C17—C18119.4 (2)
C14—O4—Zn1113.35 (13)C16—C17—H17120.3
C9—O6—H6A106 (3)C18—C17—H17120.3
C6—C1—C2118.6 (2)C26—C18—C17117.4 (2)
C6—C1—C7120.8 (2)C26—C18—C19119.1 (2)
C2—C1—C7120.6 (2)C17—C18—C19123.4 (2)
O3—C2—C3118.3 (2)C20—C19—C18120.9 (2)
O3—C2—C1122.1 (2)C20—C19—H19119.5
C3—C2—C1119.5 (2)C18—C19—H19119.5
C4—C3—C2121.2 (2)C19—C20—C21121.4 (2)
C4—C3—H3119.4C19—C20—H20119.3
C2—C3—H3119.4C21—C20—H20119.3
C3—C4—C5119.3 (3)C22—C21—C25116.4 (2)
C3—C4—H4120.3C22—C21—C20124.2 (2)
C5—C4—H4120.3C25—C21—C20119.3 (2)
C6—C5—C4120.5 (2)C23—C22—C21120.1 (2)
C6—C5—Cl1119.76 (19)C23—C22—H22120.0
C4—C5—Cl1119.7 (2)C21—C22—H22120.0
C5—C6—C1120.8 (2)C22—C23—C24119.2 (2)
C5—C6—H6119.6C22—C23—H23120.4
C1—C6—H6119.6C24—C23—H23120.4
O2—C7—O1125.1 (2)N2—C24—C23122.5 (2)
O2—C7—C1118.2 (2)N2—C24—H24118.7
O1—C7—C1116.7 (2)C23—C24—H24118.7
C13—C8—C9119.0 (2)N2—C25—C21123.3 (2)
C13—C8—C14120.0 (2)N2—C25—C26117.74 (17)
C9—C8—C14121.0 (2)C21—C25—C26118.9 (2)
O6—C9—C10118.5 (3)N1—C26—C18122.7 (2)
O6—C9—C8122.1 (2)N1—C26—C25116.99 (19)
C10—C9—C8119.4 (3)C18—C26—C25120.32 (18)
C11—C10—C9120.9 (3)Zn1—O7—H7B112.3 (16)
C11—C10—H10119.6Zn1—O7—H7A115.6 (17)
C9—C10—H10119.6H7B—O7—H7A105 (3)
C10—C11—C12119.6 (3)
O1—Zn1—N1—C1581.8 (2)C10—C11—C12—C130.1 (4)
O4—Zn1—N1—C1599.7 (2)C10—C11—C12—Cl2178.2 (2)
O7—Zn1—N1—C1512.4 (2)C11—C12—C13—C80.4 (3)
N2—Zn1—N1—C15177.0 (2)Cl2—C12—C13—C8177.89 (16)
O1—Zn1—N1—C2695.23 (15)C9—C8—C13—C120.8 (3)
O4—Zn1—N1—C2683.21 (17)C14—C8—C13—C12177.21 (19)
O7—Zn1—N1—C26170.52 (15)Zn1—O4—C14—O57.2 (2)
N2—Zn1—N1—C260.08 (14)Zn1—O4—C14—C8171.40 (13)
O1—Zn1—N2—C2482.48 (19)C13—C8—C14—O5176.59 (19)
O4—Zn1—N2—C2442.21 (19)C9—C8—C14—O51.3 (3)
N1—Zn1—N2—C24179.75 (19)C13—C8—C14—O42.1 (3)
O7—Zn1—N2—C24143.2 (2)C9—C8—C14—O4179.99 (17)
O1—Zn1—N2—C2598.22 (15)C26—N1—C15—C160.5 (4)
O4—Zn1—N2—C25137.10 (14)Zn1—N1—C15—C16177.5 (2)
N1—Zn1—N2—C250.95 (14)N1—C15—C16—C170.7 (4)
O7—Zn1—N2—C2536.1 (3)C15—C16—C17—C181.1 (4)
O4—Zn1—O1—C724.4 (2)C16—C17—C18—C260.3 (4)
N1—Zn1—O1—C7156.85 (18)C16—C17—C18—C19178.7 (2)
O7—Zn1—O1—C766.96 (19)C26—C18—C19—C200.4 (4)
N2—Zn1—O1—C7124.25 (19)C17—C18—C19—C20178.5 (2)
O1—Zn1—O4—C14176.53 (12)C18—C19—C20—C210.4 (4)
N1—Zn1—O4—C141.62 (17)C19—C20—C21—C22179.5 (2)
O7—Zn1—O4—C1489.13 (14)C19—C20—C21—C250.4 (4)
N2—Zn1—O4—C1475.44 (14)C25—C21—C22—C232.3 (3)
C6—C1—C2—O3177.31 (19)C20—C21—C22—C23177.7 (2)
C7—C1—C2—O31.7 (3)C21—C22—C23—C240.9 (4)
C6—C1—C2—C32.1 (3)C25—N2—C24—C230.9 (3)
C7—C1—C2—C3178.89 (19)Zn1—N2—C24—C23178.34 (17)
O3—C2—C3—C4177.8 (2)C22—C23—C24—N20.8 (4)
C1—C2—C3—C41.7 (3)C24—N2—C25—C210.7 (3)
C2—C3—C4—C50.2 (4)Zn1—N2—C25—C21179.95 (16)
C3—C4—C5—C60.7 (3)C24—N2—C25—C26178.95 (18)
C3—C4—C5—Cl1179.04 (18)Zn1—N2—C25—C261.7 (2)
C4—C5—C6—C10.3 (3)C22—C21—C25—N22.3 (3)
Cl1—C5—C6—C1179.52 (15)C20—C21—C25—N2177.8 (2)
C2—C1—C6—C51.2 (3)C22—C21—C25—C26179.5 (2)
C7—C1—C6—C5179.84 (17)C20—C21—C25—C260.5 (3)
Zn1—O1—C7—O22.0 (3)C15—N1—C26—C181.4 (3)
Zn1—O1—C7—C1177.15 (13)Zn1—N1—C26—C18178.73 (17)
C6—C1—C7—O2170.38 (18)C15—N1—C26—C25178.12 (19)
C2—C1—C7—O28.6 (3)Zn1—N1—C26—C250.8 (2)
C6—C1—C7—O18.9 (3)C17—C18—C26—N11.0 (3)
C2—C1—C7—O1172.16 (18)C19—C18—C26—N1180.0 (2)
C13—C8—C9—O6179.8 (2)C17—C18—C26—C25178.5 (2)
C14—C8—C9—O61.9 (3)C19—C18—C26—C250.5 (3)
C13—C8—C9—C100.8 (3)N2—C25—C26—N11.7 (3)
C14—C8—C9—C10177.2 (2)C21—C25—C26—N1179.96 (19)
O6—C9—C10—C11179.5 (2)N2—C25—C26—C18177.8 (2)
C8—C9—C10—C110.5 (4)C21—C25—C26—C180.5 (3)
C9—C10—C11—C120.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.85 (1)1.78 (2)2.552 (3)151 (2)
O6—H6A···O50.85 (1)1.80 (2)2.577 (3)150 (2)
O7—H7A···O4i0.85 (1)1.97 (1)2.785 (3)162 (3)
O7—H7B···O2i0.84 (1)1.84 (1)2.672 (3)171 (2)
Symmetry code: (i) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formula[Zn(C7H4ClO3)2(C12H8N2)(H2O)]
Mr606.69
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.681 (4), 11.777 (6), 12.982 (9)
α, β, γ (°)72.06 (2), 76.98 (2), 81.592 (19)
V3)1225.9 (12)
Z2
Radiation typeMo Kα
µ (mm1)1.27
Crystal size (mm)0.28 × 0.26 × 0.25
Data collection
DiffractometerRigaku R-AXIS RAPID Weissenberg IP
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12131, 5553, 4462
Rint0.049
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.084, 1.04
No. of reflections5553
No. of parameters355
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.54, 0.44

Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).

Selected geometric parameters (Å, º) top
Zn1—O11.9706 (18)Zn1—O72.1154 (17)
Zn1—O42.0094 (17)Zn1—N22.1599 (18)
Zn1—N12.099 (2)
O1—Zn1—O4123.68 (8)N1—Zn1—O789.25 (7)
O1—Zn1—N198.46 (8)O1—Zn1—N296.73 (8)
O4—Zn1—N1137.84 (7)O4—Zn1—N294.37 (7)
O1—Zn1—O794.31 (8)N1—Zn1—N278.09 (8)
O4—Zn1—O788.75 (7)O7—Zn1—N2164.28 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.85 (1)1.78 (2)2.552 (3)151 (2)
O6—H6A···O50.85 (1)1.80 (2)2.577 (3)150 (2)
O7—H7A···O4i0.85 (1)1.97 (1)2.785 (3)162 (3)
O7—H7B···O2i0.84 (1)1.84 (1)2.672 (3)171 (2)
Symmetry code: (i) x+1, y+2, z+2.
 

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