Bis[6-(3,5-dimethyl-1H-pyrazol-1-yl-κN2)picolinato-κ2N,O]zinc(II) trihydrate

Yin, X.-H.; Zhao, K.; Feng, Y.; Zhu, J.

doi:10.1107/S1600536807054608

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Bis[6-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)picolinato-κ²N,O]zinc(II) trihydrate

X.-H. Yin, K. Zhao, Y. Feng and J. Zhu

In the title compound, [Zn(C₁₁H₁₀N₃O₂)₂]·3H₂O, the Zn^II atom is coordinated by four N and two O atoms in a distorted octahedral geometry. One water molecule is disordered equally over two positions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054608/sg2196sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054608/sg2196Isup2.hkl Contains datablock I

CCDC reference: 665043

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
Disorder in solvent or counterion
R factor = 0.042
wR factor = 0.125
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6B    ..  H7D     ..       2.07 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6B    ..  H7E     ..       1.97 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C12    -   C13    ...       1.53 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N4  -ZN1 -N1  -C6     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N4  -ZN1 -N1  -C2     -5.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            N1  -ZN1 -N4  -C17   -84.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            N1  -ZN1 -N4  -C13    88.00  2.00   1.555   1.555   1.555   1.555

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In recent years, there has been an increasing interest in the coordination chemistry due to the increased recognition of it's role in catalysis enzymatic reactions, magnetism and molecular architectures (Costamagna et al., 1992; Bhatia et al., 1981). We report here the crystal structure of a new zinc(II) complex with the ligand 6- (3,5-dimethyl-1H-pyrazol-1-yl) picolinic acid(DPPA).(I) (Fig.1).

The title compound, (I), consists of a zinc(II) complex cation and three uncoordinated water molecules. In the cation(Fig. 1), the Co atom is six-coordinated by four N atoms and two O atoms from two DPPA ligands. The Zn(II) atom is a slightly distorted octahedral environment. The Zn—O bond length is 2.109 (3) and 2.122 (3) Å,The Zn—N distances range from 2.077 (3) to 2.219 (3) Å, i.e. normal values. The C1—C2 bond length is 1.528 (5) Å, being in the normal C—C ranges in cobaltcarboxylate complexes.The angles around Zn(II) atom are from 73.01 (10) to 177.31 (10)°. The DPPA molecule acts as a bidentate ligand.

Related literature top

For related literature, see: Bhatia et al. (1981); Costamagna et al. (1992).

Experimental top

6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid, and ZnCl₂. 6H₂O were available commercially and were used without further purification. Equimolar 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 217 mg) was dissolved in anhydrous alcohol (15 ml). The mixture was stirred to give a clear solution, To this solution was added ZnCl₂.6H₂O (0.5 mmol, 119 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, dark red prisms of the title compound were formed. The crystals were isolated, washed with alcohol three times and dried in a vacuum desiccator using silica gel (Yield 75%). Elemental analysis: found: C, 47.78; H, 4.85; N, 15.13; O, 20.39; calc. for C₂₂H₂₆Zn_N6_O7: C, 47.88; H, 4.75; N, 15.23; O, 20.29

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of the title compound (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing of (I) showing the hydrogen bonded interactions as dashed lines.

Bis[6-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)picolinato-κ²N,O]zinc(II) trihydrate top

Crystal data top

[Zn(C₁₁H₁₀N₃O₂)₂]·3H₂O	Z = 2
M_r = 551.86	F(000) = 572
Triclinic, P1	D_x = 1.490 Mg m⁻³
a = 9.8071 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8388 (12) Å	Cell parameters from 3006 reflections
c = 12.6766 (16) Å	θ = 2.2–25.9°
α = 71.334 (2)°	µ = 1.05 mm⁻¹
β = 74.505 (2)°	T = 298 K
γ = 84.772 (3)°	Block, colorless
V = 1230.2 (2) Å³	0.50 × 0.48 × 0.34 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4251 independent reflections
Radiation source: fine-focus sealed tube	3192 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.621, T_max = 0.716	k = −12→12
6315 measured reflections	l = −15→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0638P)² + 0.5328P] where P = (F_o² + 2F_c²)/3
4251 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Zn(C₁₁H₁₀N₃O₂)₂]·3H₂O	γ = 84.772 (3)°
M_r = 551.86	V = 1230.2 (2) Å³
Triclinic, P1	Z = 2
a = 9.8071 (9) Å	Mo Kα radiation
b = 10.8388 (12) Å	µ = 1.05 mm⁻¹
c = 12.6766 (16) Å	T = 298 K
α = 71.334 (2)°	0.50 × 0.48 × 0.34 mm
β = 74.505 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4251 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3192 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.716	R_int = 0.021
6315 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
4251 reflections	Δρ_min = −0.38 e Å⁻³
334 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	Occ. (<1)
Zn1	0.78562 (4)	0.71982 (4)	0.72699 (4)	0.04776 (17)
N1	0.8809 (3)	0.8979 (2)	0.6879 (2)	0.0383 (6)
N2	1.0937 (3)	0.8039 (3)	0.6297 (2)	0.0415 (6)
N3	1.0155 (3)	0.6935 (3)	0.6573 (2)	0.0432 (7)
N4	0.6810 (3)	0.5449 (2)	0.7692 (2)	0.0382 (6)
N5	0.7234 (3)	0.4926 (3)	0.9470 (2)	0.0445 (7)
N6	0.7831 (3)	0.6137 (3)	0.9073 (3)	0.0500 (7)
O1	0.6140 (3)	0.8407 (3)	0.7764 (3)	0.0775 (9)
O2	0.5565 (3)	1.0410 (3)	0.7860 (3)	0.0882 (10)
O3	0.7335 (3)	0.7301 (3)	0.5734 (2)	0.0631 (7)
O4	0.6151 (3)	0.6316 (3)	0.4964 (2)	0.0604 (7)
O5	0.6801 (4)	0.8398 (4)	0.2929 (3)	0.1290 (17)
H5A	0.6557	0.7771	0.3548	0.155*
H5B	0.6060	0.8730	0.2720	0.155*
O6	0.0977 (5)	0.0193 (5)	0.8593 (4)	0.1492 (18)
H6A	0.1701	0.0622	0.8137	0.179*
H6B	0.1187	−0.0245	0.9216	0.179*
O7	0.8467 (7)	0.1337 (7)	0.9299 (5)	0.095 (2)	0.50
H7D	0.7748	0.0855	0.9498	0.113*	0.50
H7E	0.9202	0.0906	0.9094	0.113*	0.50
O8	0.6242 (9)	0.0134 (8)	0.9945 (6)	0.131 (3)	0.50
H8A	0.5892	0.0190	0.9386	0.157*	0.50
H8B	0.5582	−0.0035	1.0561	0.157*	0.50
C1	0.6401 (4)	0.9559 (4)	0.7605 (4)	0.0607 (10)
C2	0.7947 (4)	0.9962 (3)	0.7060 (3)	0.0471 (8)
C3	0.8450 (5)	1.1204 (4)	0.6748 (4)	0.0624 (11)
H3	0.7846	1.1883	0.6876	0.075*
C4	0.9862 (5)	1.1418 (4)	0.6245 (4)	0.0698 (12)
H4	1.0222	1.2254	0.6014	0.084*
C5	1.0746 (4)	1.0412 (3)	0.6078 (3)	0.0586 (10)
H5	1.1709	1.0549	0.5745	0.070*
C6	1.0172 (3)	0.9183 (3)	0.6419 (3)	0.0401 (7)
C7	1.3505 (4)	0.8774 (4)	0.5519 (4)	0.0664 (11)
H7A	1.4403	0.8362	0.5319	0.100*
H7B	1.3475	0.9097	0.6147	0.100*
H7C	1.3378	0.9484	0.4867	0.100*
C8	1.2346 (4)	0.7804 (4)	0.5869 (3)	0.0479 (8)
C9	1.2439 (4)	0.6538 (4)	0.5886 (3)	0.0542 (9)
H9	1.3260	0.6091	0.5650	0.065*
C10	1.1074 (4)	0.6037 (3)	0.6322 (3)	0.0466 (8)
C11	1.0586 (5)	0.4695 (4)	0.6528 (4)	0.0672 (11)
H11A	1.0213	0.4290	0.7338	0.101*
H11B	1.1370	0.4190	0.6243	0.101*
H11C	0.9862	0.4742	0.6135	0.101*
C12	0.6603 (3)	0.6400 (4)	0.5754 (3)	0.0475 (8)
C13	0.6244 (3)	0.5298 (3)	0.6900 (3)	0.0409 (8)
C14	0.5401 (4)	0.4242 (3)	0.7133 (3)	0.0506 (9)
H14	0.5027	0.4128	0.6570	0.061*
C15	0.5132 (4)	0.3362 (3)	0.8224 (4)	0.0581 (10)
H15	0.4557	0.2649	0.8403	0.070*
C16	0.5703 (4)	0.3526 (3)	0.9051 (4)	0.0562 (10)
H16	0.5516	0.2943	0.9792	0.067*
C17	0.6566 (3)	0.4596 (3)	0.8736 (3)	0.0410 (8)
C18	0.6907 (5)	0.2913 (5)	1.1241 (4)	0.0839 (15)
H18A	0.5892	0.2888	1.1455	0.126*
H18B	0.7252	0.2645	1.1922	0.126*
H18C	0.7268	0.2334	1.0793	0.126*
C19	0.7389 (4)	0.4274 (4)	1.0543 (3)	0.0550 (9)
C20	0.8090 (5)	0.5092 (4)	1.0815 (4)	0.0683 (11)
H20	0.8359	0.4921	1.1499	0.082*
C21	0.8344 (4)	0.6234 (4)	0.9900 (3)	0.0586 (10)
C22	0.9040 (6)	0.7455 (5)	0.9796 (4)	0.0874 (15)
H22A	0.9557	0.7839	0.9012	0.131*
H22B	0.9678	0.7251	1.0286	0.131*
H22C	0.8331	0.8057	1.0022	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0398 (3)	0.0390 (2)	0.0616 (3)	−0.01119 (17)	−0.00741 (19)	−0.01302 (19)
N1	0.0382 (15)	0.0338 (14)	0.0419 (15)	−0.0030 (11)	−0.0058 (12)	−0.0131 (12)
N2	0.0337 (15)	0.0418 (15)	0.0484 (17)	−0.0082 (12)	−0.0060 (12)	−0.0147 (13)
N3	0.0382 (15)	0.0382 (15)	0.0549 (17)	−0.0030 (12)	−0.0093 (13)	−0.0181 (13)
N4	0.0299 (14)	0.0380 (14)	0.0459 (16)	−0.0034 (11)	−0.0060 (12)	−0.0139 (13)
N5	0.0404 (16)	0.0452 (16)	0.0454 (17)	−0.0098 (13)	−0.0081 (13)	−0.0104 (13)
N6	0.0505 (18)	0.0460 (17)	0.0533 (18)	−0.0136 (14)	−0.0101 (14)	−0.0139 (14)
O1	0.0384 (15)	0.0589 (18)	0.116 (3)	−0.0053 (13)	0.0062 (15)	−0.0210 (17)
O2	0.072 (2)	0.077 (2)	0.099 (2)	0.0321 (17)	−0.0020 (18)	−0.0289 (18)
O3	0.0582 (16)	0.0646 (17)	0.0608 (17)	−0.0278 (13)	−0.0192 (13)	−0.0005 (13)
O4	0.0574 (16)	0.0719 (18)	0.0553 (16)	−0.0067 (13)	−0.0205 (13)	−0.0173 (14)
O5	0.080 (2)	0.153 (4)	0.115 (3)	−0.041 (2)	−0.044 (2)	0.038 (3)
O6	0.129 (4)	0.166 (5)	0.126 (4)	−0.039 (3)	−0.019 (3)	−0.010 (3)
O7	0.091 (5)	0.140 (6)	0.073 (4)	0.026 (4)	−0.025 (4)	−0.064 (4)
O8	0.148 (7)	0.145 (7)	0.065 (5)	0.030 (6)	0.015 (5)	−0.028 (5)
C1	0.053 (2)	0.054 (2)	0.063 (3)	0.0125 (19)	−0.0038 (19)	−0.014 (2)
C2	0.054 (2)	0.0384 (19)	0.047 (2)	0.0061 (16)	−0.0117 (17)	−0.0136 (16)
C3	0.083 (3)	0.038 (2)	0.070 (3)	0.006 (2)	−0.020 (2)	−0.0228 (19)
C4	0.086 (3)	0.041 (2)	0.083 (3)	−0.020 (2)	−0.014 (3)	−0.021 (2)
C5	0.053 (2)	0.050 (2)	0.073 (3)	−0.0167 (18)	−0.006 (2)	−0.022 (2)
C6	0.0387 (18)	0.0407 (18)	0.0419 (19)	−0.0071 (14)	−0.0069 (15)	−0.0147 (15)
C7	0.036 (2)	0.080 (3)	0.070 (3)	−0.0162 (19)	−0.0033 (18)	−0.010 (2)
C8	0.0353 (19)	0.065 (2)	0.040 (2)	−0.0056 (16)	−0.0071 (15)	−0.0127 (17)
C9	0.041 (2)	0.066 (3)	0.054 (2)	0.0098 (18)	−0.0102 (17)	−0.0214 (19)
C10	0.046 (2)	0.047 (2)	0.051 (2)	0.0061 (16)	−0.0133 (16)	−0.0218 (17)
C11	0.067 (3)	0.050 (2)	0.091 (3)	0.0059 (19)	−0.021 (2)	−0.032 (2)
C12	0.0327 (18)	0.057 (2)	0.053 (2)	−0.0024 (16)	−0.0107 (16)	−0.0168 (17)
C13	0.0324 (17)	0.0436 (18)	0.051 (2)	0.0008 (14)	−0.0089 (15)	−0.0212 (16)
C14	0.048 (2)	0.045 (2)	0.069 (3)	−0.0004 (16)	−0.0194 (18)	−0.0272 (19)
C15	0.059 (2)	0.0376 (19)	0.080 (3)	−0.0138 (17)	−0.023 (2)	−0.0139 (19)
C16	0.058 (2)	0.0375 (19)	0.067 (3)	−0.0127 (17)	−0.0168 (19)	−0.0049 (18)
C17	0.0358 (18)	0.0367 (17)	0.048 (2)	−0.0010 (14)	−0.0079 (15)	−0.0117 (15)
C18	0.096 (4)	0.083 (3)	0.060 (3)	−0.036 (3)	−0.026 (3)	0.011 (2)
C19	0.051 (2)	0.061 (2)	0.047 (2)	−0.0128 (18)	−0.0057 (17)	−0.0093 (18)
C20	0.072 (3)	0.086 (3)	0.049 (2)	−0.018 (2)	−0.019 (2)	−0.015 (2)
C21	0.055 (2)	0.068 (3)	0.058 (2)	−0.0155 (19)	−0.0137 (19)	−0.023 (2)
C22	0.105 (4)	0.082 (3)	0.088 (3)	−0.035 (3)	−0.036 (3)	−0.025 (3)

Geometric parameters (Å, º) top

Zn1—N1	2.077 (3)	C4—C5	1.364 (6)
Zn1—N4	2.084 (3)	C4—H4	0.9300
Zn1—O3	2.109 (3)	C5—C6	1.385 (4)
Zn1—O1	2.122 (3)	C5—H5	0.9300
Zn1—N6	2.200 (3)	C7—C8	1.498 (5)
Zn1—N3	2.219 (3)	C7—H7A	0.9600
N1—C6	1.315 (4)	C7—H7B	0.9600
N1—C2	1.339 (4)	C7—H7C	0.9600
N2—C8	1.376 (4)	C8—C9	1.361 (5)
N2—N3	1.377 (3)	C9—C10	1.392 (5)
N2—C6	1.420 (4)	C9—H9	0.9300
N3—C10	1.322 (4)	C10—C11	1.493 (5)
N4—C17	1.323 (4)	C11—H11A	0.9600
N4—C13	1.328 (4)	C11—H11B	0.9600
N5—C19	1.359 (5)	C11—H11C	0.9600
N5—N6	1.371 (4)	C12—C13	1.534 (5)
N5—C17	1.416 (4)	C13—C14	1.380 (5)
N6—C21	1.313 (5)	C14—C15	1.378 (5)
O1—C1	1.239 (5)	C14—H14	0.9300
O2—C1	1.240 (5)	C15—C16	1.377 (5)
O3—C12	1.253 (4)	C15—H15	0.9300
O4—C12	1.230 (4)	C16—C17	1.387 (5)
O5—H5A	0.8500	C16—H16	0.9300
O5—H5B	0.8500	C18—C19	1.500 (5)
O6—H6A	0.8500	C18—H18A	0.9600
O6—H6B	0.8499	C18—H18B	0.9600
O7—H7D	0.8499	C18—H18C	0.9600
O7—H7E	0.8499	C19—C20	1.346 (6)
O8—H8A	0.8500	C20—C21	1.387 (6)
O8—H8B	0.8500	C20—H20	0.9300
C1—C2	1.528 (5)	C21—C22	1.496 (5)
C2—C3	1.374 (5)	C22—H22A	0.9600
C3—C4	1.367 (6)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600

N1—Zn1—N4	177.31 (10)	H7A—C7—H7B	109.5
N1—Zn1—O3	103.44 (10)	C8—C7—H7C	109.5
N4—Zn1—O3	76.71 (10)	H7A—C7—H7C	109.5
N1—Zn1—O1	76.63 (10)	H7B—C7—H7C	109.5
N4—Zn1—O1	100.68 (11)	C9—C8—N2	106.2 (3)
O3—Zn1—O1	93.81 (12)	C9—C8—C7	129.0 (4)
N1—Zn1—N6	106.66 (10)	N2—C8—C7	124.7 (3)
N4—Zn1—N6	73.18 (10)	C8—C9—C10	107.1 (3)
O3—Zn1—N6	149.89 (10)	C8—C9—H9	126.5
O1—Zn1—N6	92.03 (12)	C10—C9—H9	126.5
N1—Zn1—N3	73.01 (10)	N3—C10—C9	110.7 (3)
N4—Zn1—N3	109.68 (10)	N3—C10—C11	120.3 (3)
O3—Zn1—N3	94.08 (10)	C9—C10—C11	129.0 (3)
O1—Zn1—N3	149.62 (11)	C10—C11—H11A	109.5
N6—Zn1—N3	95.67 (11)	C10—C11—H11B	109.5
C6—N1—C2	120.2 (3)	H11A—C11—H11B	109.5
C6—N1—Zn1	123.3 (2)	C10—C11—H11C	109.5
C2—N1—Zn1	116.4 (2)	H11A—C11—H11C	109.5
C8—N2—N3	110.3 (3)	H11B—C11—H11C	109.5
C8—N2—C6	132.7 (3)	O4—C12—O3	127.0 (3)
N3—N2—C6	116.8 (2)	O4—C12—C13	117.7 (3)
C10—N3—N2	105.8 (3)	O3—C12—C13	115.3 (3)
C10—N3—Zn1	140.6 (2)	N4—C13—C14	121.2 (3)
N2—N3—Zn1	113.60 (18)	N4—C13—C12	113.6 (3)
C17—N4—C13	120.8 (3)	C14—C13—C12	125.2 (3)
C17—N4—Zn1	122.4 (2)	C15—C14—C13	118.1 (3)
C13—N4—Zn1	116.4 (2)	C15—C14—H14	120.9
C19—N5—N6	110.9 (3)	C13—C14—H14	120.9
C19—N5—C17	132.4 (3)	C16—C15—C14	120.8 (3)
N6—N5—C17	116.7 (3)	C16—C15—H15	119.6
C21—N6—N5	105.8 (3)	C14—C15—H15	119.6
C21—N6—Zn1	139.6 (3)	C15—C16—C17	117.4 (3)
N5—N6—Zn1	114.1 (2)	C15—C16—H16	121.3
C1—O1—Zn1	117.6 (2)	C17—C16—H16	121.3
C12—O3—Zn1	117.6 (2)	N4—C17—C16	121.8 (3)
H5A—O5—H5B	108.5	N4—C17—N5	112.9 (3)
H6A—O6—H6B	108.5	C16—C17—N5	125.3 (3)
H7D—O7—H7E	108.6	C19—C18—H18A	109.5
H8A—O8—H8B	108.7	C19—C18—H18B	109.5
O1—C1—O2	127.8 (4)	H18A—C18—H18B	109.5
O1—C1—C2	115.7 (3)	C19—C18—H18C	109.5
O2—C1—C2	116.5 (4)	H18A—C18—H18C	109.5
N1—C2—C3	121.2 (3)	H18B—C18—H18C	109.5
N1—C2—C1	113.5 (3)	C20—C19—N5	105.4 (3)
C3—C2—C1	125.3 (3)	C20—C19—C18	128.3 (4)
C4—C3—C2	118.4 (4)	N5—C19—C18	126.3 (4)
C4—C3—H3	120.8	C19—C20—C21	108.2 (4)
C2—C3—H3	120.8	C19—C20—H20	125.9
C5—C4—C3	120.4 (4)	C21—C20—H20	125.9
C5—C4—H4	119.8	N6—C21—C20	109.7 (3)
C3—C4—H4	119.8	N6—C21—C22	121.4 (4)
C4—C5—C6	118.2 (4)	C20—C21—C22	128.9 (4)
C4—C5—H5	120.9	C21—C22—H22A	109.5
C6—C5—H5	120.9	C21—C22—H22B	109.5
N1—C6—C5	121.5 (3)	H22A—C22—H22B	109.5
N1—C6—N2	113.0 (3)	C21—C22—H22C	109.5
C5—C6—N2	125.4 (3)	H22A—C22—H22C	109.5
C8—C7—H7A	109.5	H22B—C22—H22C	109.5
C8—C7—H7B	109.5

N4—Zn1—N1—C6	179 (100)	O2—C1—C2—N1	175.7 (3)
O3—Zn1—N1—C6	−88.5 (3)	O1—C1—C2—C3	175.9 (4)
O1—Zn1—N1—C6	−179.2 (3)	O2—C1—C2—C3	−5.6 (6)
N6—Zn1—N1—C6	92.7 (3)	N1—C2—C3—C4	0.0 (6)
N3—Zn1—N1—C6	1.7 (2)	C1—C2—C3—C4	−178.6 (4)
N4—Zn1—N1—C2	−5 (2)	C2—C3—C4—C5	−1.2 (6)
O3—Zn1—N1—C2	87.9 (2)	C3—C4—C5—C6	0.8 (6)
O1—Zn1—N1—C2	−2.8 (2)	C2—N1—C6—C5	−2.0 (5)
N6—Zn1—N1—C2	−90.9 (2)	Zn1—N1—C6—C5	174.2 (3)
N3—Zn1—N1—C2	178.1 (3)	C2—N1—C6—N2	179.4 (3)
C8—N2—N3—C10	0.2 (3)	Zn1—N1—C6—N2	−4.4 (4)
C6—N2—N3—C10	176.0 (3)	C4—C5—C6—N1	0.8 (6)
C8—N2—N3—Zn1	−179.8 (2)	C4—C5—C6—N2	179.2 (3)
C6—N2—N3—Zn1	−4.1 (3)	C8—N2—C6—N1	180.0 (3)
N1—Zn1—N3—C10	−178.7 (4)	N3—N2—C6—N1	5.4 (4)
N4—Zn1—N3—C10	1.5 (4)	C8—N2—C6—C5	1.5 (6)
O3—Zn1—N3—C10	−75.9 (4)	N3—N2—C6—C5	−173.1 (3)
O1—Zn1—N3—C10	179.5 (3)	N3—N2—C8—C9	−0.3 (4)
N6—Zn1—N3—C10	75.6 (4)	C6—N2—C8—C9	−175.1 (3)
N1—Zn1—N3—N2	1.4 (2)	N3—N2—C8—C7	−177.8 (3)
N4—Zn1—N3—N2	−178.5 (2)	C6—N2—C8—C7	7.3 (6)
O3—Zn1—N3—N2	104.2 (2)	N2—C8—C9—C10	0.2 (4)
O1—Zn1—N3—N2	−0.5 (4)	C7—C8—C9—C10	177.6 (4)
N6—Zn1—N3—N2	−104.3 (2)	N2—N3—C10—C9	−0.1 (4)
N1—Zn1—N4—C17	−84 (2)	Zn1—N3—C10—C9	−180.0 (3)
O3—Zn1—N4—C17	−177.9 (3)	N2—N3—C10—C11	179.4 (3)
O1—Zn1—N4—C17	−86.4 (3)	Zn1—N3—C10—C11	−0.6 (6)
N6—Zn1—N4—C17	2.4 (2)	C8—C9—C10—N3	−0.1 (4)
N3—Zn1—N4—C17	92.5 (3)	C8—C9—C10—C11	−179.5 (4)
N1—Zn1—N4—C13	88 (2)	Zn1—O3—C12—O4	177.0 (3)
O3—Zn1—N4—C13	−5.7 (2)	Zn1—O3—C12—C13	−2.9 (4)
O1—Zn1—N4—C13	85.7 (2)	C17—N4—C13—C14	−0.8 (5)
N6—Zn1—N4—C13	174.6 (2)	Zn1—N4—C13—C14	−173.1 (2)
N3—Zn1—N4—C13	−95.3 (2)	C17—N4—C13—C12	178.3 (3)
C19—N5—N6—C21	−0.4 (4)	Zn1—N4—C13—C12	6.0 (3)
C17—N5—N6—C21	178.3 (3)	O4—C12—C13—N4	178.1 (3)
C19—N5—N6—Zn1	173.5 (2)	O3—C12—C13—N4	−2.1 (4)
C17—N5—N6—Zn1	−7.7 (3)	O4—C12—C13—C14	−2.9 (5)
N1—Zn1—N6—C21	−8.9 (4)	O3—C12—C13—C14	177.0 (3)
N4—Zn1—N6—C21	173.9 (4)	N4—C13—C14—C15	1.6 (5)
O3—Zn1—N6—C21	173.4 (4)	C12—C13—C14—C15	−177.3 (3)
O1—Zn1—N6—C21	−85.5 (4)	C13—C14—C15—C16	−0.8 (6)
N3—Zn1—N6—C21	65.1 (4)	C14—C15—C16—C17	−0.8 (6)
N1—Zn1—N6—N5	−179.8 (2)	C13—N4—C17—C16	−0.9 (5)
N4—Zn1—N6—N5	3.0 (2)	Zn1—N4—C17—C16	170.9 (3)
O3—Zn1—N6—N5	2.4 (4)	C13—N4—C17—N5	−179.0 (3)
O1—Zn1—N6—N5	103.5 (2)	Zn1—N4—C17—N5	−7.2 (4)
N3—Zn1—N6—N5	−105.9 (2)	C15—C16—C17—N4	1.7 (5)
N1—Zn1—O1—C1	1.3 (3)	C15—C16—C17—N5	179.5 (3)
N4—Zn1—O1—C1	−178.8 (3)	C19—N5—C17—N4	−172.0 (3)
O3—Zn1—O1—C1	−101.6 (3)	N6—N5—C17—N4	9.6 (4)
N6—Zn1—O1—C1	107.9 (3)	C19—N5—C17—C16	10.0 (6)
N3—Zn1—O1—C1	3.1 (5)	N6—N5—C17—C16	−168.4 (3)
N1—Zn1—O3—C12	−172.6 (3)	N6—N5—C19—C20	0.1 (4)
N4—Zn1—O3—C12	4.6 (3)	C17—N5—C19—C20	−178.4 (4)
O1—Zn1—O3—C12	−95.5 (3)	N6—N5—C19—C18	−178.3 (4)
N6—Zn1—O3—C12	5.2 (4)	C17—N5—C19—C18	3.2 (7)
N3—Zn1—O3—C12	113.9 (3)	N5—C19—C20—C21	0.3 (5)
Zn1—O1—C1—O2	−177.9 (4)	C18—C19—C20—C21	178.6 (4)
Zn1—O1—C1—C2	0.3 (5)	N5—N6—C21—C20	0.6 (4)
C6—N1—C2—C3	1.6 (5)	Zn1—N6—C21—C20	−170.8 (3)
Zn1—N1—C2—C3	−174.9 (3)	N5—N6—C21—C22	−177.8 (4)
C6—N1—C2—C1	−179.7 (3)	Zn1—N6—C21—C22	10.8 (7)
Zn1—N1—C2—C1	3.8 (4)	C19—C20—C21—N6	−0.6 (5)
O1—C1—C2—N1	−2.7 (5)	C19—C20—C21—C22	177.7 (4)

Experimental details

Crystal data
Chemical formula	[Zn(C₁₁H₁₀N₃O₂)₂]·3H₂O
M_r	551.86
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.8071 (9), 10.8388 (12), 12.6766 (16)
α, β, γ (°)	71.334 (2), 74.505 (2), 84.772 (3)
V (Å³)	1230.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.50 × 0.48 × 0.34

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.621, 0.716
No. of measured, independent and observed [I > 2σ(I)] reflections	6315, 4251, 3192
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 1.04
No. of reflections	4251
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.38

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected bond lengths (Å) top

Zn1—N1	2.077 (3)	Zn1—O1	2.122 (3)
Zn1—N4	2.084 (3)	Zn1—N6	2.200 (3)
Zn1—O3	2.109 (3)	Zn1—N3	2.219 (3)

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