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

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ISSN: 2056-9890

Propane-1,2-diaminium tris­­(pyridine-2,6-di­carboxyl­ato-κ3O2,N,O6)zirconate(IV) trihydrate

aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: h_pasdar@iau-tnb.ac.ir

(Received 5 February 2011; accepted 6 March 2011; online 13 April 2011)

In the title compound, (C3H12N2)[Zr(C7H3NO4)3]·3H2O, the ZrIV cation is chelated by three pyridine-2,6-dicarboxyl­ate anions in a distorted tricapped trigonal–prismatic environment. The crystal structure is stabilized by inter­molecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the background to proton-transfer compounds, see: Aghabozorg et al. (2008[Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran Chem. Soc. 5, 184-227.]). For related structures, see: Aghabozorg et al. (2005[Aghabozorg, H., Moghimi, A., Manteghi, F. & Ranjbar, M. (2005). Z. Anorg. Allg. Chem. 631, 909-913.]); Daneshvar et al. (2008[Daneshvar, S., Aghabozorg, H. & Manteghi, F. (2008). Acta Cryst. E64, m1308-m1309.]); Pasdar et al. (2010a[Pasdar, H., Heidari, S., Aghabozorg, H. & Notash, B. (2010a). Acta Cryst. E66, m1581.],b[Pasdar, H., Majdolashrafi, M., Aghabozorg, H. & Khavasi, H. R. (2010b). Acta Cryst. E66, o3043.], 2011a[Pasdar, H., Ebdam, A., Aghabozorg, H. & Notash, B. (2011a). Acta Cryst. E67, m294.],b[Pasdar, H., Sadat Kashani, S., Aghabozorg, H. & Notash, B. (2011b). Acta Cryst. E67, m193-m194.]).

[Scheme 1]

Experimental

Crystal data
  • (C3H12N2)[Zr(C7H3NO4)3]·3H2O

  • Mr = 716.73

  • Monoclinic, P 21 /n

  • a = 10.515 (2) Å

  • b = 19.195 (4) Å

  • c = 14.149 (3) Å

  • β = 103.39 (3)°

  • V = 2778.1 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.48 mm−1

  • T = 298 K

  • 0.25 × 0.15 × 0.15 mm

Data collection
  • Stoe IPDS II diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.915, Tmax = 0.926

  • 21838 measured reflections

  • 7481 independent reflections

  • 5264 reflections with I > 2σ(I)

  • Rint = 0.133

Refinement
  • R[F2 > 2σ(F2)] = 0.086

  • wR(F2) = 0.206

  • S = 1.18

  • 7481 reflections

  • 427 parameters

  • 7 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.09 e Å−3

  • Δρmin = −0.77 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O13—H13A⋯O14 0.80 (8) 2.10 (9) 2.745 (11) 138 (13)
O13—H13B⋯O2i 0.80 (4) 2.10 (8) 2.793 (8) 145 (12)
O14—H14A⋯O5ii 0.91 (8) 2.11 (9) 2.978 (7) 158 (12)
O14—H14B⋯O8 0.85 (4) 1.89 (5) 2.731 (9) 171 (14)
O15—H15A⋯O12 0.98 (9) 1.91 (10) 2.857 (8) 164 (12)
O15—H15B⋯O1iii 0.83 (4) 2.46 (7) 3.227 (9) 155 (13)
N4—H4A⋯O10iv 0.89 1.92 2.791 (8) 165
N4—H4B⋯O6ii 0.89 2.24 2.851 (7) 125
N4—H4C⋯O15v 0.89 2.04 2.864 (10) 154
N5—H5A⋯O13 0.89 1.94 2.769 (9) 154
N5—H5B⋯O6iv 0.89 2.18 2.844 (8) 131
N5—H5C⋯O4 0.89 1.91 2.776 (8) 163
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) -x+2, -y+1, -z+1; (iv) x-1, y, z; (v) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED32. Stoe & Cie, Darmstadt, Germany.]); data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Pyridine-2,6-dicarboxylic acid (pydcH2) was commonly used by Aghabozorg and his co-workers as an acid in proton transfer systems (Aghabozorg et al. 2008). Our group have been focused on forming ion pairs between 2,6-pydcH2 and various organic bases (Pasdar et al., 2010a; Pasdar et al. 2011a,b). The structure of two proton transfer compound containing nine-coordinated [ZrIV(2,6-pydc)3]2- moiety were reported with the counter cationic part of 2,6-pyridinediamine(Aghabozorg et al. 2005) and 2,4,6-triamino-1,3,5-triazine (Daneshvar et al. 2008), respectively. Recently, we report the structure of (2a6mpH)2[Zr(2,6-pydc)3].2H2O (Pasdar et al. 2011a).

Herein, we report the synthesis and crystal structure of (1,2-pdaH2)[Zr(2,6-pydc)3].3H2O. The title compound was prepared by the reaction of ZrCl4.3H2O, propane-1,2-diamine and 2,6-pyridinedicarboxylic acid in aqueous solution. Fig.1 present the molecular structure of the title compound. X-ray diffraction study shows that Zirconium(IV) ion is coordinated by three pydc2- moiety in a distorted tricapped trigonal prismatic geometry and pydc2- ligands act as tridentate ligand. Coordination environment around Zirconium(IV) ion in the (1,2-pdaH2)[Zr(2,6-pydc)3].3H2O is presented in Fig. 2. The Zr—N and Zr—O bond lengths and angles are in the normal ranges (Aghabozorg et al. 2005; Daneshvar et al. 2008). The crystal packing diagram of the title compound is shown in Fig. 3. In the crystal packing diagram of the title compound, there are several intermolecular N—H···O, O—H···O hydrogen bonds which play an important role in stabilization of crystal structure (Table 1 and Fig. 3).

Related literature top

For the background to proton-transfer compounds, see: Aghabozorg et al. (2008). For related structures, see: Aghabozorg et al. (2005); Daneshvar et al. (2008); Pasdar et al. (2010a,b, 2011a,b).

Experimental top

A solution of propane-1,2-diamine (0.074 g, 1 mmol) in water (8 ml) and 2,6-pyridinedicarboxylic acid (0.501 g, 3 mmol) in water (10 ml) were mixed and stirred until clear solution obtained. Then a solution of ZrCl4.3H2O (0.116 g, 0.5 mmol) in water (5 ml) was added to the mixture of acid-base and stirrer for 5 h. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation after one month at room temperature (m.p: 210 °C).

Refinement top

Water H atoms were found in a difference Fourier map and positional parameters were refined, Uiso(H) = 0.115 Å2. Ammonium H atoms were positioned geometrically and refined as riding atoms with N—H = 0.89 Å and Uiso(H) = 1.5Ueq(N). Other H atoms were positioned geometrically and refined as riding atoms with C—H = 0.93-0.98 Å, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The coordination environment around ZrIV ion in the title compound.
[Figure 3] Fig. 3. The packing diagram of the title compound. The intermolecular N—H···O, O—H···O hydrogen bonds are shown as dashed lines.
Propane-1,2-diaminium tris(pyridine-2,6-dicarboxylato- κ3O2,N,O6)zirconate(IV) trihydrate top
Crystal data top
(C3H12N2)[Zr(C7H3NO4)3]·3H2OF(000) = 1464
Mr = 716.73Dx = 1.714 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7481 reflections
a = 10.515 (2) Åθ = 2.1–29.2°
b = 19.195 (4) ŵ = 0.48 mm1
c = 14.149 (3) ÅT = 298 K
β = 103.39 (3)°Prism, colorless
V = 2778.1 (10) Å30.25 × 0.15 × 0.15 mm
Z = 4
Data collection top
Stoe IPDS II
diffractometer
7481 independent reflections
Radiation source: fine-focus sealed tube5264 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.133
rotation method scansθmax = 29.2°, θmin = 2.1°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
h = 1411
Tmin = 0.915, Tmax = 0.926k = 2626
21838 measured reflectionsl = 1919
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H atoms treated by a mixture of independent and constrained refinement
S = 1.18 w = 1/[σ2(Fo2) + (0.0753P)2 + 3.9962P]
where P = (Fo2 + 2Fc2)/3
7481 reflections(Δ/σ)max = 0.001
427 parametersΔρmax = 1.09 e Å3
7 restraintsΔρmin = 0.77 e Å3
Crystal data top
(C3H12N2)[Zr(C7H3NO4)3]·3H2OV = 2778.1 (10) Å3
Mr = 716.73Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.515 (2) ŵ = 0.48 mm1
b = 19.195 (4) ÅT = 298 K
c = 14.149 (3) Å0.25 × 0.15 × 0.15 mm
β = 103.39 (3)°
Data collection top
Stoe IPDS II
diffractometer
7481 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
5264 reflections with I > 2σ(I)
Tmin = 0.915, Tmax = 0.926Rint = 0.133
21838 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0867 restraints
wR(F2) = 0.206H atoms treated by a mixture of independent and constrained refinement
S = 1.18Δρmax = 1.09 e Å3
7481 reflectionsΔρmin = 0.77 e Å3
427 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
C181.0667 (8)0.5828 (4)0.6397 (5)0.0486 (18)
H181.09020.56630.70320.058*
O130.3681 (10)0.8559 (3)0.2972 (5)0.084 (2)
O140.5141 (7)0.8422 (4)0.4841 (5)0.0666 (18)
Zr10.93403 (5)0.68252 (3)0.29848 (3)0.02015 (14)
O110.7886 (4)0.6046 (2)0.3278 (3)0.0299 (9)
O51.0314 (4)0.7169 (2)0.1812 (3)0.0285 (8)
O91.1276 (4)0.7203 (2)0.3786 (3)0.0281 (8)
O30.7472 (4)0.7187 (2)0.2025 (3)0.0281 (8)
N20.9428 (5)0.8044 (2)0.2844 (3)0.0250 (9)
O70.8366 (4)0.7374 (2)0.4015 (3)0.0318 (9)
O11.0691 (4)0.5933 (2)0.2947 (3)0.0311 (9)
N30.9968 (5)0.6338 (2)0.4535 (3)0.0242 (9)
N10.8636 (5)0.6103 (2)0.1615 (3)0.0242 (9)
O40.5741 (4)0.7014 (3)0.0797 (3)0.0364 (10)
C70.6845 (6)0.6870 (3)0.1263 (4)0.0279 (11)
C151.1900 (6)0.6989 (3)0.4611 (4)0.0254 (11)
O61.1211 (5)0.7982 (3)0.1045 (3)0.0385 (10)
O21.1365 (5)0.5005 (2)0.2250 (4)0.0421 (11)
O80.7646 (6)0.8342 (3)0.4614 (4)0.0499 (13)
C60.7542 (6)0.6251 (3)0.0975 (4)0.0278 (11)
C20.9348 (6)0.5542 (3)0.1484 (4)0.0282 (11)
C91.0020 (6)0.8333 (3)0.2204 (4)0.0267 (11)
C11.0562 (6)0.5475 (3)0.2271 (4)0.0276 (11)
C81.0568 (5)0.7797 (3)0.1625 (4)0.0266 (11)
C140.8231 (6)0.8035 (3)0.4075 (4)0.0307 (12)
C130.8855 (6)0.8446 (3)0.3394 (4)0.0287 (12)
O101.3031 (4)0.7132 (3)0.5023 (3)0.0359 (10)
O120.6980 (5)0.5485 (3)0.4335 (3)0.0429 (11)
C161.1115 (6)0.6500 (3)0.5102 (4)0.0273 (11)
C40.7813 (8)0.5259 (4)0.0028 (5)0.0460 (17)
H40.75310.49740.05110.055*
C200.9149 (6)0.5919 (3)0.4871 (4)0.0283 (11)
C210.7902 (6)0.5797 (3)0.4117 (4)0.0308 (12)
C30.8944 (7)0.5103 (3)0.0707 (5)0.0375 (14)
H30.94260.47070.06390.045*
C110.9459 (8)0.9464 (3)0.2640 (5)0.0440 (17)
H110.94670.99460.25700.053*
C50.7101 (7)0.5843 (4)0.0153 (5)0.0406 (15)
H50.63420.59610.03030.049*
C190.9465 (8)0.5654 (4)0.5800 (5)0.0440 (16)
H190.88870.53650.60220.053*
C120.8857 (7)0.9168 (3)0.3310 (5)0.0378 (14)
H120.84600.94450.36980.045*
C171.1515 (6)0.6252 (4)0.6036 (4)0.0363 (14)
H171.23350.63650.64170.044*
C101.0048 (7)0.9048 (3)0.2074 (5)0.0380 (14)
H101.04530.92410.16170.046*
N50.3816 (6)0.7484 (3)0.1693 (4)0.0407 (13)
H5A0.38720.79030.19690.061*
H5B0.30910.74600.12220.061*
H5C0.45090.74130.14440.061*
C230.3774 (7)0.6935 (4)0.2445 (5)0.0379 (14)
H230.30490.70400.27510.045*
C220.5033 (7)0.6975 (4)0.3206 (5)0.0419 (16)
H22A0.57250.67600.29580.050*
H22B0.52630.74600.33420.050*
N40.4933 (6)0.6623 (4)0.4117 (4)0.0493 (16)
H4A0.43890.68600.43940.074*
H4B0.57200.66050.45200.074*
H4C0.46310.61920.39830.074*
C240.3509 (10)0.6242 (4)0.1930 (5)0.053 (2)
H24A0.41430.61650.15490.080*
H24B0.26480.62460.15120.080*
H24C0.35690.58770.24010.080*
O150.6503 (7)0.4645 (4)0.5884 (5)0.077 (2)
H15A0.672 (13)0.485 (7)0.531 (7)0.115*
H14A0.497 (14)0.820 (7)0.537 (8)0.115*
H14B0.592 (6)0.835 (7)0.479 (10)0.115*
H13A0.426 (11)0.870 (7)0.340 (8)0.115*
H13B0.342 (13)0.892 (4)0.271 (8)0.115*
H15B0.728 (6)0.453 (8)0.601 (10)0.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C180.053 (4)0.059 (4)0.029 (3)0.008 (4)0.000 (3)0.019 (3)
O130.141 (8)0.037 (3)0.070 (4)0.017 (4)0.017 (5)0.005 (3)
O140.072 (4)0.072 (4)0.066 (4)0.018 (4)0.037 (3)0.026 (3)
Zr10.0211 (2)0.0215 (2)0.0184 (2)0.0005 (2)0.00570 (16)0.0007 (2)
O110.032 (2)0.032 (2)0.0257 (18)0.0045 (17)0.0058 (16)0.0019 (16)
O50.035 (2)0.027 (2)0.0275 (19)0.0021 (17)0.0147 (17)0.0016 (15)
O90.029 (2)0.028 (2)0.0282 (19)0.0051 (16)0.0097 (16)0.0039 (15)
O30.030 (2)0.029 (2)0.0250 (18)0.0030 (16)0.0057 (16)0.0003 (15)
N20.026 (2)0.024 (2)0.027 (2)0.0010 (18)0.0093 (18)0.0020 (16)
O70.038 (2)0.034 (2)0.0275 (19)0.0006 (18)0.0161 (18)0.0001 (17)
O10.037 (2)0.031 (2)0.0264 (19)0.0058 (18)0.0080 (17)0.0005 (16)
N30.027 (2)0.024 (2)0.023 (2)0.0020 (18)0.0079 (18)0.0026 (17)
N10.026 (2)0.025 (2)0.023 (2)0.0015 (18)0.0070 (18)0.0011 (17)
O40.024 (2)0.047 (3)0.037 (2)0.0043 (18)0.0039 (18)0.0041 (19)
C70.030 (3)0.028 (3)0.027 (2)0.003 (2)0.010 (2)0.004 (2)
C150.025 (3)0.024 (3)0.027 (2)0.001 (2)0.007 (2)0.0047 (19)
O60.037 (2)0.049 (3)0.034 (2)0.001 (2)0.0153 (19)0.0118 (19)
O20.043 (3)0.026 (2)0.059 (3)0.010 (2)0.017 (2)0.004 (2)
O80.056 (3)0.053 (3)0.050 (3)0.007 (2)0.030 (3)0.011 (2)
C60.032 (3)0.028 (3)0.027 (2)0.006 (2)0.012 (2)0.002 (2)
C20.030 (3)0.027 (3)0.031 (3)0.002 (2)0.014 (2)0.000 (2)
C90.023 (3)0.026 (3)0.030 (3)0.000 (2)0.004 (2)0.003 (2)
C10.030 (3)0.020 (2)0.035 (3)0.001 (2)0.013 (2)0.003 (2)
C80.023 (3)0.033 (3)0.023 (2)0.001 (2)0.003 (2)0.006 (2)
C140.028 (3)0.037 (3)0.028 (3)0.003 (2)0.009 (2)0.006 (2)
C130.026 (3)0.031 (3)0.027 (3)0.000 (2)0.003 (2)0.005 (2)
O100.023 (2)0.049 (3)0.034 (2)0.0060 (19)0.0039 (17)0.001 (2)
O120.036 (2)0.050 (3)0.045 (2)0.011 (2)0.013 (2)0.016 (2)
C160.029 (3)0.029 (3)0.023 (2)0.004 (2)0.003 (2)0.001 (2)
C40.053 (4)0.048 (4)0.039 (3)0.011 (3)0.014 (3)0.014 (3)
C200.028 (3)0.030 (3)0.026 (2)0.002 (2)0.006 (2)0.004 (2)
C210.028 (3)0.033 (3)0.031 (3)0.004 (2)0.007 (2)0.003 (2)
C30.050 (4)0.028 (3)0.039 (3)0.002 (3)0.019 (3)0.005 (2)
C110.063 (5)0.024 (3)0.045 (3)0.002 (3)0.013 (3)0.003 (3)
C50.040 (4)0.049 (4)0.031 (3)0.004 (3)0.003 (3)0.008 (3)
C190.047 (4)0.050 (4)0.036 (3)0.008 (3)0.011 (3)0.013 (3)
C120.041 (4)0.029 (3)0.040 (3)0.007 (3)0.002 (3)0.008 (3)
C170.031 (3)0.041 (3)0.032 (3)0.003 (3)0.000 (2)0.007 (3)
C100.044 (4)0.032 (3)0.037 (3)0.008 (3)0.009 (3)0.008 (2)
N50.042 (3)0.038 (3)0.043 (3)0.004 (2)0.012 (3)0.009 (2)
C230.035 (3)0.045 (4)0.037 (3)0.002 (3)0.013 (3)0.004 (3)
C220.037 (4)0.049 (4)0.040 (3)0.002 (3)0.007 (3)0.004 (3)
N40.044 (3)0.072 (4)0.032 (3)0.008 (3)0.010 (3)0.001 (3)
C240.079 (6)0.041 (4)0.040 (4)0.013 (4)0.013 (4)0.001 (3)
O150.071 (4)0.091 (5)0.068 (4)0.024 (4)0.014 (4)0.031 (4)
Geometric parameters (Å, º) top
C18—C171.388 (10)C9—C101.387 (8)
C18—C191.389 (10)C9—C81.509 (8)
C18—H180.9300C14—C131.508 (9)
O13—H13A0.80 (8)C13—C121.392 (9)
O13—H13B0.80 (4)O12—C211.239 (8)
O14—H14A0.91 (8)C16—C171.376 (8)
O14—H14B0.85 (4)C4—C31.378 (10)
Zr1—O92.210 (4)C4—C51.382 (11)
Zr1—O32.225 (4)C4—H40.9300
Zr1—O72.230 (4)C20—C191.377 (8)
Zr1—O12.233 (4)C20—C211.504 (8)
Zr1—O52.241 (4)C3—H30.9300
Zr1—O112.245 (4)C11—C101.375 (10)
Zr1—N32.334 (4)C11—C121.379 (11)
Zr1—N22.352 (4)C11—H110.9300
Zr1—N12.358 (4)C5—H50.9300
O11—C211.277 (7)C19—H190.9300
O5—C81.275 (7)C12—H120.9300
O9—C151.267 (7)C17—H170.9300
O3—C71.280 (7)C10—H100.9300
N2—C91.333 (7)N5—C231.506 (8)
N2—C131.334 (7)N5—H5A0.8900
O7—C141.283 (7)N5—H5B0.8900
O1—C11.283 (7)N5—H5C0.8900
N3—C161.321 (7)C23—C221.502 (9)
N3—C201.343 (7)C23—C241.510 (10)
N1—C61.320 (7)C23—H230.9800
N1—C21.350 (7)C22—N41.480 (9)
O4—C71.226 (7)C22—H22A0.9700
C7—C61.502 (8)C22—H22B0.9700
C15—O101.227 (7)N4—H4A0.8900
C15—C161.521 (8)N4—H4B0.8900
O6—C81.230 (7)N4—H4C0.8900
O2—C11.241 (7)C24—H24A0.9600
O8—C141.233 (8)C24—H24B0.9600
C6—C51.390 (8)C24—H24C0.9600
C2—C31.372 (8)O15—H15A0.98 (9)
C2—C11.492 (8)O15—H15B0.83 (4)
C17—C18—C19119.2 (6)O6—C8—O5125.9 (6)
C17—C18—H18120.4O6—C8—C9120.2 (5)
C19—C18—H18120.4O5—C8—C9114.0 (5)
H13A—O13—H13B100 (8)O8—C14—O7126.3 (6)
H14A—O14—H14B111 (10)O8—C14—C13119.9 (6)
O9—Zr1—O3142.08 (15)O7—C14—C13113.7 (5)
O9—Zr1—O791.02 (16)N2—C13—C12121.0 (6)
O3—Zr1—O777.11 (15)N2—C13—C14113.2 (5)
O9—Zr1—O175.43 (16)C12—C13—C14125.8 (6)
O3—Zr1—O1134.53 (15)N3—C16—C17122.3 (6)
O7—Zr1—O1140.25 (15)N3—C16—C15112.5 (5)
O9—Zr1—O576.03 (15)C17—C16—C15125.1 (5)
O3—Zr1—O586.94 (15)C3—C4—C5119.6 (6)
O7—Zr1—O5134.60 (16)C3—C4—H4120.2
O1—Zr1—O578.81 (15)C5—C4—H4120.2
O9—Zr1—O11135.19 (14)N3—C20—C19121.8 (6)
O3—Zr1—O1177.16 (15)N3—C20—C21111.6 (5)
O7—Zr1—O1176.04 (16)C19—C20—C21126.7 (6)
O1—Zr1—O1187.57 (16)O12—C21—O11124.8 (6)
O5—Zr1—O11141.28 (15)O12—C21—C20120.2 (5)
O9—Zr1—N367.84 (15)O11—C21—C20115.0 (5)
O3—Zr1—N3135.72 (16)C2—C3—C4118.8 (6)
O7—Zr1—N369.39 (16)C2—C3—H3120.6
O1—Zr1—N370.89 (15)C4—C3—H3120.6
O5—Zr1—N3137.31 (16)C10—C11—C12120.1 (6)
O11—Zr1—N367.44 (15)C10—C11—H11120.0
O9—Zr1—N270.58 (16)C12—C11—H11120.0
O3—Zr1—N271.60 (16)C4—C5—C6118.5 (6)
O7—Zr1—N267.56 (16)C4—C5—H5120.7
O1—Zr1—N2136.30 (17)C6—C5—H5120.7
O5—Zr1—N267.09 (15)C20—C19—C18118.5 (6)
O11—Zr1—N2136.09 (16)C20—C19—H19120.8
N3—Zr1—N2118.01 (16)C18—C19—H19120.8
O9—Zr1—N1133.70 (16)C11—C12—C13118.7 (6)
O3—Zr1—N167.48 (15)C11—C12—H12120.7
O7—Zr1—N1135.26 (16)C13—C12—H12120.7
O1—Zr1—N167.05 (15)C16—C17—C18118.5 (6)
O5—Zr1—N171.04 (16)C16—C17—H17120.8
O11—Zr1—N170.27 (16)C18—C17—H17120.8
N3—Zr1—N1120.25 (16)C11—C10—C9118.2 (6)
N2—Zr1—N1121.74 (15)C11—C10—H10120.9
C21—O11—Zr1123.9 (4)C9—C10—H10120.9
C8—O5—Zr1125.9 (4)C23—N5—H5A109.5
C15—O9—Zr1125.8 (4)C23—N5—H5B109.5
C7—O3—Zr1125.1 (4)H5A—N5—H5B109.5
C9—N2—C13120.1 (5)C23—N5—H5C109.5
C9—N2—Zr1120.3 (4)H5A—N5—H5C109.5
C13—N2—Zr1119.6 (4)H5B—N5—H5C109.5
C14—O7—Zr1125.9 (4)C22—C23—N5107.8 (6)
C1—O1—Zr1125.8 (4)C22—C23—C24115.1 (7)
C16—N3—C20119.7 (5)N5—C23—C24107.9 (6)
C16—N3—Zr1119.8 (4)C22—C23—H23108.6
C20—N3—Zr1120.5 (4)N5—C23—H23108.6
C6—N1—C2120.1 (5)C24—C23—H23108.6
C6—N1—Zr1119.7 (4)N4—C22—C23111.8 (6)
C2—N1—Zr1120.2 (4)N4—C22—H22A109.3
O4—C7—O3125.8 (6)C23—C22—H22A109.3
O4—C7—C6119.5 (5)N4—C22—H22B109.3
O3—C7—C6114.6 (5)C23—C22—H22B109.3
O10—C15—O9127.1 (6)H22A—C22—H22B107.9
O10—C15—C16119.3 (5)C22—N4—H4A109.5
O9—C15—C16113.6 (5)C22—N4—H4B109.5
N1—C6—C5121.5 (6)H4A—N4—H4B109.5
N1—C6—C7112.7 (5)C22—N4—H4C109.5
C5—C6—C7125.7 (6)H4A—N4—H4C109.5
N1—C2—C3121.4 (6)H4B—N4—H4C109.5
N1—C2—C1111.8 (5)C23—C24—H24A109.5
C3—C2—C1126.7 (6)C23—C24—H24B109.5
N2—C9—C10121.9 (6)H24A—C24—H24B109.5
N2—C9—C8112.5 (5)C23—C24—H24C109.5
C10—C9—C8125.5 (6)H24A—C24—H24C109.5
O2—C1—O1124.1 (6)H24B—C24—H24C109.5
O2—C1—C2120.9 (5)H15A—O15—H15B83 (10)
O1—C1—C2115.0 (5)
O9—Zr1—O11—C2115.8 (6)O9—Zr1—N1—C238.3 (5)
O3—Zr1—O11—C21140.9 (5)O3—Zr1—N1—C2179.9 (5)
O7—Zr1—O11—C2161.2 (5)O7—Zr1—N1—C2139.5 (4)
O1—Zr1—O11—C2182.2 (5)O1—Zr1—N1—C20.2 (4)
O5—Zr1—O11—C21150.9 (4)O5—Zr1—N1—C285.4 (4)
N3—Zr1—O11—C2111.9 (4)O11—Zr1—N1—C296.1 (4)
N2—Zr1—O11—C2195.6 (5)N3—Zr1—N1—C249.0 (5)
N1—Zr1—O11—C21148.7 (5)N2—Zr1—N1—C2131.2 (4)
O9—Zr1—O5—C869.6 (4)Zr1—O3—C7—O4170.3 (4)
O3—Zr1—O5—C876.2 (4)Zr1—O3—C7—C66.6 (7)
O7—Zr1—O5—C87.7 (5)Zr1—O9—C15—O10171.2 (5)
O1—Zr1—O5—C8147.2 (5)Zr1—O9—C15—C168.1 (7)
O11—Zr1—O5—C8141.2 (4)C2—N1—C6—C50.6 (9)
N3—Zr1—O5—C8102.2 (5)Zr1—N1—C6—C5179.3 (5)
N2—Zr1—O5—C84.9 (4)C2—N1—C6—C7177.0 (5)
N1—Zr1—O5—C8143.4 (5)Zr1—N1—C6—C73.1 (6)
O3—Zr1—O9—C15142.8 (4)O4—C7—C6—N1171.2 (5)
O7—Zr1—O9—C1572.6 (4)O3—C7—C6—N15.9 (7)
O1—Zr1—O9—C1569.5 (4)O4—C7—C6—C56.2 (9)
O5—Zr1—O9—C15151.4 (5)O3—C7—C6—C5176.6 (6)
O11—Zr1—O9—C151.6 (5)C6—N1—C2—C31.8 (8)
N3—Zr1—O9—C155.4 (4)Zr1—N1—C2—C3178.3 (4)
N2—Zr1—O9—C15138.4 (5)C6—N1—C2—C1178.6 (5)
N1—Zr1—O9—C15105.9 (5)Zr1—N1—C2—C11.3 (6)
O9—Zr1—O3—C7137.0 (4)C13—N2—C9—C101.0 (9)
O7—Zr1—O3—C7148.3 (5)Zr1—N2—C9—C10177.4 (5)
O1—Zr1—O3—C73.5 (5)C13—N2—C9—C8177.9 (5)
O5—Zr1—O3—C774.5 (4)Zr1—N2—C9—C80.5 (6)
O11—Zr1—O3—C770.0 (4)Zr1—O1—C1—O2176.4 (4)
N3—Zr1—O3—C7107.1 (4)Zr1—O1—C1—C23.6 (7)
N2—Zr1—O3—C7141.3 (5)N1—C2—C1—O2177.0 (5)
N1—Zr1—O3—C73.8 (4)C3—C2—C1—O23.4 (9)
O9—Zr1—N2—C980.1 (4)N1—C2—C1—O12.9 (7)
O3—Zr1—N2—C997.0 (4)C3—C2—C1—O1176.7 (6)
O7—Zr1—N2—C9179.7 (5)Zr1—O5—C8—O6172.6 (4)
O1—Zr1—N2—C939.2 (5)Zr1—O5—C8—C96.3 (6)
O5—Zr1—N2—C92.4 (4)N2—C9—C8—O6175.6 (5)
O11—Zr1—N2—C9143.9 (4)C10—C9—C8—O67.6 (9)
N3—Zr1—N2—C9130.3 (4)N2—C9—C8—O53.3 (7)
N1—Zr1—N2—C949.9 (5)C10—C9—C8—O5173.5 (6)
O9—Zr1—N2—C13101.4 (4)Zr1—O7—C14—O8176.7 (5)
O3—Zr1—N2—C1381.4 (4)Zr1—O7—C14—C132.5 (7)
O7—Zr1—N2—C131.9 (4)C9—N2—C13—C120.3 (9)
O1—Zr1—N2—C13142.4 (4)Zr1—N2—C13—C12178.1 (4)
O5—Zr1—N2—C13176.0 (5)C9—N2—C13—C14179.8 (5)
O11—Zr1—N2—C1334.5 (5)Zr1—N2—C13—C141.4 (6)
N3—Zr1—N2—C1351.2 (5)O8—C14—C13—N2178.7 (6)
N1—Zr1—N2—C13128.5 (4)O7—C14—C13—N20.5 (7)
O9—Zr1—O7—C1470.8 (5)O8—C14—C13—C120.8 (10)
O3—Zr1—O7—C1472.8 (5)O7—C14—C13—C12180.0 (6)
O1—Zr1—O7—C14139.0 (4)C20—N3—C16—C170.3 (9)
O5—Zr1—O7—C140.4 (6)Zr1—N3—C16—C17177.4 (5)
O11—Zr1—O7—C14152.5 (5)C20—N3—C16—C15178.9 (5)
N3—Zr1—O7—C14136.7 (5)Zr1—N3—C16—C151.8 (6)
N2—Zr1—O7—C142.4 (5)O10—C15—C16—N3173.5 (5)
N1—Zr1—O7—C14110.7 (5)O9—C15—C16—N35.9 (7)
O9—Zr1—O1—C1150.1 (5)O10—C15—C16—C177.4 (9)
O3—Zr1—O1—C12.4 (6)O9—C15—C16—C17173.2 (6)
O7—Zr1—O1—C1136.3 (4)C16—N3—C20—C190.4 (9)
O5—Zr1—O1—C171.8 (5)Zr1—N3—C20—C19176.6 (5)
O11—Zr1—O1—C171.7 (5)C16—N3—C20—C21179.9 (5)
N3—Zr1—O1—C1138.7 (5)Zr1—N3—C20—C213.1 (7)
N2—Zr1—O1—C1110.4 (5)Zr1—O11—C21—O12164.3 (5)
N1—Zr1—O1—C12.1 (4)Zr1—O11—C21—C2014.5 (7)
O9—Zr1—N3—C161.3 (4)N3—C20—C21—O12172.3 (6)
O3—Zr1—N3—C16144.6 (4)C19—C20—C21—O127.4 (10)
O7—Zr1—N3—C16101.3 (4)N3—C20—C21—O116.7 (8)
O1—Zr1—N3—C1680.3 (4)C19—C20—C21—O11173.7 (7)
O5—Zr1—N3—C1633.0 (5)N1—C2—C3—C42.7 (9)
O11—Zr1—N3—C16175.8 (5)C1—C2—C3—C4177.8 (6)
N2—Zr1—N3—C1652.7 (5)C5—C4—C3—C21.2 (11)
N1—Zr1—N3—C16127.5 (4)C3—C4—C5—C61.0 (11)
O9—Zr1—N3—C20175.7 (5)N1—C6—C5—C41.9 (10)
O3—Zr1—N3—C2032.4 (5)C7—C6—C5—C4175.3 (6)
O7—Zr1—N3—C2075.7 (4)N3—C20—C19—C180.1 (11)
O1—Zr1—N3—C20102.7 (5)C21—C20—C19—C18179.7 (7)
O5—Zr1—N3—C20150.0 (4)C17—C18—C19—C201.0 (12)
O11—Zr1—N3—C207.2 (4)C10—C11—C12—C130.3 (10)
N2—Zr1—N3—C20124.3 (4)N2—C13—C12—C110.4 (10)
N1—Zr1—N3—C2055.5 (5)C14—C13—C12—C11179.1 (6)
O9—Zr1—N1—C6141.6 (4)N3—C16—C17—C181.4 (10)
O3—Zr1—N1—C60.2 (4)C15—C16—C17—C18177.6 (6)
O7—Zr1—N1—C640.6 (5)C19—C18—C17—C161.8 (12)
O1—Zr1—N1—C6179.9 (5)C12—C11—C10—C90.3 (10)
O5—Zr1—N1—C694.5 (4)N2—C9—C10—C111.0 (10)
O11—Zr1—N1—C684.0 (4)C8—C9—C10—C11177.5 (6)
N3—Zr1—N1—C6131.1 (4)N5—C23—C22—N4162.0 (6)
N2—Zr1—N1—C648.7 (5)C24—C23—C22—N477.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13A···O140.80 (8)2.10 (9)2.745 (11)138 (13)
O13—H13B···O2i0.80 (4)2.10 (8)2.793 (8)145 (12)
O14—H14A···O5ii0.91 (8)2.11 (9)2.978 (7)158 (12)
O14—H14B···O80.85 (4)1.89 (5)2.731 (9)171 (14)
O15—H15A···O120.98 (9)1.91 (10)2.857 (8)164 (12)
O15—H15B···O1iii0.83 (4)2.46 (7)3.227 (9)155 (13)
N4—H4A···O10iv0.891.922.791 (8)165
N4—H4B···O6ii0.892.242.851 (7)125
N4—H4C···O15v0.892.042.864 (10)154
N5—H5A···O130.891.942.769 (9)154
N5—H5B···O6iv0.892.182.844 (8)131
N5—H5C···O40.891.912.776 (8)163
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x1/2, y+3/2, z+1/2; (iii) x+2, y+1, z+1; (iv) x1, y, z; (v) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula(C3H12N2)[Zr(C7H3NO4)3]·3H2O
Mr716.73
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.515 (2), 19.195 (4), 14.149 (3)
β (°) 103.39 (3)
V3)2778.1 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.48
Crystal size (mm)0.25 × 0.15 × 0.15
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correctionNumerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
Tmin, Tmax0.915, 0.926
No. of measured, independent and
observed [I > 2σ(I)] reflections
21838, 7481, 5264
Rint0.133
(sin θ/λ)max1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.206, 1.18
No. of reflections7481
No. of parameters427
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.09, 0.77

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13A···O140.80 (8)2.10 (9)2.745 (11)138 (13)
O13—H13B···O2i0.80 (4)2.10 (8)2.793 (8)145 (12)
O14—H14A···O5ii0.91 (8)2.11 (9)2.978 (7)158 (12)
O14—H14B···O80.85 (4)1.89 (5)2.731 (9)171 (14)
O15—H15A···O120.98 (9)1.91 (10)2.857 (8)164 (12)
O15—H15B···O1iii0.83 (4)2.46 (7)3.227 (9)155 (13)
N4—H4A···O10iv0.891.922.791 (8)164.9
N4—H4B···O6ii0.892.242.851 (7)125.2
N4—H4C···O15v0.892.042.864 (10)154.4
N5—H5A···O130.891.942.769 (9)153.9
N5—H5B···O6iv0.892.182.844 (8)131.3
N5—H5C···O40.891.912.776 (8)163.4
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x1/2, y+3/2, z+1/2; (iii) x+2, y+1, z+1; (iv) x1, y, z; (v) x+1, y+1, z+1.
 

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

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First citationPasdar, H., Sadat Kashani, S., Aghabozorg, H. & Notash, B. (2011b). Acta Cryst. E67, m193–m194.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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