Tri­aqua(4-hydroxy­pyridine-2,6-di­carboxyl­ato-κ³N,O,O′)­zinc(II)–aceto­nitrile–water(1/0.25/1)

The title compound, [Zn(C₇H₂NO₅)(H₂O)₃]·0.25CH₃CN·H₂O, was synthesized by the reaction of Zn(CH₃COO)₂·2H₂O and chelidamic acid. The coordination geometry of the Zn atom is a distorted octahedron, with one N and two O atoms from the chelidamate ligand and three water O atoms. A three-dimensional network is formed by the O—H...O hydrogen bonds between the O atoms of the chelidamate ligand and the aqua ligands and water mol­ecule of crystallization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• H-atom completeness 38%
• Disorder in solvent or counterion
• R factor = 0.052
• wR factor = 0.154
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1W    ..  N22      =       2.68 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O1W    ..  O12      =       2.72 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O2W    ..  O13      =       2.66 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O2W    ..  N22      =       2.74 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O2W    ..  O14      =       2.83 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O3W    ..  O12      =       2.82 Ang.

Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    8
           From the CIF: _chemical_formula_weight           327.79
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01    7.50   90.08
           H         1.01    4.00    4.03
           N        14.01    1.25   17.51
           O        16.00    9.00  143.99
           Zn       65.39    1.00   65.39
           Calculated formula weight              321.00
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     327.79
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT076_ALERT_1_C Occupancy       0.50 less than 1.0 for Sp.pos  .        C21
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C21
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.15
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C7.5 H10.75 N1.25 O9 Zn1
            Atom count from the _atom_site data:  C7.5 H4 N1.25 O9 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C7.50 H10.75 N1.25 O9 Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         60.00     60.00    0.00
           H         86.00     32.00   54.00
           N         10.00     10.00    0.00
           O         72.00     72.00    0.00
           Zn         8.00      8.00    0.00

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

[Zn(C7H2NO5)(H2O)3].0.25(C2H3N).(H2O)	F(000) = 1332
Mr = 327.79	Dx = 1.866 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6504 (3) Å	Cell parameters from 2863 reflections
b = 7.0380 (2) Å	θ = 2.8–25.0°
c = 22.6423 (5) Å	µ = 2.15 mm^−1
β = 91.866 (1)°	T = 293 K
V = 2333.4 (1) Å^3	Prism, pale yellow
Z = 8	0.64 × 0.40 × 0.38 mm

Data collection

Siemens SMART CCD diffractometer	2059 independent reflections
Radiation source: fine-focus sealed tube	1759 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→17
Tmin = 0.296, Tmax = 0.442	k = −5→8
3823 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1023P)^2 + 10.2923P] where P = (Fo^2 + 2Fc^2)/3
2059 reflections	(Δ/σ)max = 0.003
185 parameters	Δρmax = 0.95 e Å^−3
13 restraints	Δρmin = −1.05 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.484546 (13)	0.75804 (3)	0.638008 (8)	0.02755 (6)
O11	0.52753 (8)	0.79294 (17)	0.54425 (5)	0.0271 (3)
O12	0.48014 (9)	0.73097 (17)	0.45117 (6)	0.0311 (3)
O13	0.38768 (8)	0.6649 (2)	0.70344 (5)	0.0387 (4)
O14	0.25846 (12)	0.5052 (3)	0.71115 (8)	0.0855 (5)
O15	0.17042 (7)	0.42029 (17)	0.48796 (5)	0.0308 (3)
N1	0.38201 (8)	0.64013 (19)	0.58848 (6)	0.0232 (3)
C11	0.38537 (10)	0.6371 (2)	0.52955 (6)	0.0188 (4)
C12	0.31516 (10)	0.5608 (2)	0.49423 (7)	0.0224 (4)
H12A	0.3185	0.5581	0.4533	0.027*
C13	0.23905 (10)	0.4880 (2)	0.52263 (7)	0.0219 (4)
C14	0.23687 (11)	0.4900 (2)	0.58407 (7)	0.0270 (4)
H14A	0.1871	0.4409	0.6035	0.032*
C15	0.31013 (11)	0.5663 (2)	0.61535 (7)	0.0287 (4)
C16	0.47032 (11)	0.7275 (2)	0.50569 (7)	0.0218 (4)
C17	0.31849 (13)	0.5795 (3)	0.68227 (8)	0.0426 (5)
C21	0.5000	0.2375 (8)	0.7500	0.064 (3)	0.50
C22	0.5821 (3)	0.2308 (8)	0.7263 (3)	0.0885 (11)	0.25
N22	0.5821 (3)	0.2308 (8)	0.7263 (3)	0.0885 (11)	0.25
O1W	0.56234 (9)	0.4984 (2)	0.64235 (6)	0.0440 (4)
O2W	0.57996 (8)	0.85417 (19)	0.69628 (5)	0.0381 (4)
O3W	0.43495 (9)	1.04405 (18)	0.63413 (5)	0.0357 (3)
O4W	0.24901 (11)	0.0591 (3)	0.66895 (7)	0.0723 (6)
H4W	0.2613 (14)	0.000 (3)	0.7059 (9)	0.047 (6)*
H15	0.1276 (17)	0.376 (4)	0.5063 (11)	0.068 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02423 (10)	0.03436 (11)	0.02387 (11)	−0.00801 (7)	−0.00218 (9)	−0.00133 (8)
O11	0.0194 (5)	0.0384 (6)	0.0237 (6)	−0.0096 (5)	0.0014 (5)	−0.0026 (5)
O12	0.0266 (6)	0.0409 (6)	0.0262 (6)	−0.0127 (5)	0.0054 (5)	−0.0023 (5)
O13	0.0382 (6)	0.0530 (7)	0.0252 (6)	−0.0178 (6)	0.0026 (5)	−0.0032 (6)
O14	0.0887 (9)	0.1196 (10)	0.0493 (8)	−0.0717 (7)	0.0182 (7)	−0.0071 (8)
O15	0.0223 (5)	0.0433 (6)	0.0266 (6)	−0.0142 (5)	−0.0022 (5)	0.0015 (5)
N1	0.0197 (6)	0.0275 (6)	0.0226 (6)	−0.0045 (5)	0.0014 (5)	0.0026 (6)
C11	0.0171 (6)	0.0211 (6)	0.0184 (7)	−0.0017 (6)	0.0002 (5)	−0.0003 (6)
C12	0.0217 (7)	0.0251 (7)	0.0203 (7)	−0.0031 (6)	−0.0007 (6)	−0.0017 (6)
C13	0.0158 (6)	0.0206 (7)	0.0292 (8)	−0.0021 (6)	−0.0001 (6)	−0.0023 (7)
C14	0.0209 (7)	0.0320 (8)	0.0285 (8)	−0.0085 (6)	0.0059 (6)	−0.0005 (7)
C15	0.0282 (7)	0.0334 (8)	0.0246 (7)	−0.0087 (7)	0.0053 (6)	−0.0008 (7)
C16	0.0185 (7)	0.0236 (7)	0.0236 (8)	−0.0002 (6)	0.0061 (6)	−0.0008 (6)
C17	0.0474 (9)	0.0556 (11)	0.0254 (8)	−0.0300 (8)	0.0077 (8)	−0.0043 (8)
C21	0.096 (6)	0.034 (3)	0.062 (5)	0.000	−0.002 (4)	0.000
C22	0.0903 (18)	0.0831 (18)	0.0918 (19)	−0.0015 (14)	−0.0031 (15)	−0.0048 (15)
N22	0.0903 (18)	0.0831 (18)	0.0918 (19)	−0.0015 (14)	−0.0031 (15)	−0.0048 (15)
O1W	0.0386 (7)	0.0441 (7)	0.0488 (8)	0.0041 (6)	−0.0076 (6)	−0.0078 (7)
O2W	0.0362 (6)	0.0478 (7)	0.0300 (6)	−0.0141 (6)	−0.0066 (5)	0.0050 (6)
O3W	0.0397 (6)	0.0343 (6)	0.0332 (6)	−0.0014 (6)	0.0005 (5)	0.0016 (6)
O4W	0.0547 (9)	0.1227 (15)	0.0396 (8)	0.0119 (10)	0.0029 (7)	0.0222 (9)

Geometric parameters (Å, º)

Zn1—O2W	2.0081 (12)	N1—C15	1.338 (2)
Zn1—N1	2.0232 (13)	C11—C12	1.390 (2)
Zn1—O3W	2.1409 (13)	C11—C16	1.513 (2)
Zn1—O1W	2.1541 (14)	C12—C13	1.402 (2)
Zn1—O13	2.1854 (13)	C12—H12A	0.9300
Zn1—O11	2.2473 (12)	C13—C14	1.393 (2)
O11—C16	1.276 (2)	C14—C15	1.376 (2)
O12—C16	1.248 (2)	C14—H14A	0.9300
O13—C17	1.260 (2)	C15—C17	1.519 (2)
O14—C17	1.230 (3)	C21—C22	1.333 (4)
O15—C13	1.3428 (19)	C21—N22^i	1.333 (4)
O15—H15	0.83 (3)	C21—C22^i	1.333 (4)
N1—C11	1.337 (2)	O4W—H4W	0.95 (2)
O2W—Zn1—N1	172.22 (5)	N1—C11—C16	114.03 (13)
O2W—Zn1—O3W	86.46 (5)	C12—C11—C16	123.98 (14)
N1—Zn1—O3W	96.78 (5)	C11—C12—C13	117.52 (14)
O2W—Zn1—O1W	84.25 (5)	C11—C12—H12A	121.2
N1—Zn1—O1W	93.41 (5)	C13—C12—H12A	121.2
O3W—Zn1—O1W	167.90 (5)	O15—C13—C14	123.13 (14)
O2W—Zn1—O13	96.27 (5)	O15—C13—C12	116.94 (14)
N1—Zn1—O13	76.46 (5)	C14—C13—C12	119.93 (14)
O3W—Zn1—O13	94.75 (5)	C15—C14—C13	118.38 (15)
O1W—Zn1—O13	93.95 (5)	C15—C14—H14A	120.8
O2W—Zn1—O11	111.92 (5)	C13—C14—H14A	120.8
N1—Zn1—O11	75.35 (5)	N1—C15—C14	122.00 (15)
O3W—Zn1—O11	87.92 (5)	N1—C15—C17	112.98 (14)
O1W—Zn1—O11	88.38 (5)	C14—C15—C17	125.02 (16)
O13—Zn1—O11	151.80 (4)	O12—C16—O11	125.12 (15)
C16—O11—Zn1	114.13 (10)	O12—C16—C11	118.96 (14)
C17—O13—Zn1	114.66 (11)	O11—C16—C11	115.91 (14)
C13—O15—H15	114.0 (17)	O14—C17—O13	125.52 (18)
C11—N1—C15	120.18 (13)	O14—C17—C15	117.93 (17)
C11—N1—Zn1	120.58 (10)	O13—C17—C15	116.54 (16)
C15—N1—Zn1	119.24 (11)	C22—C21—N22^i	175.9 (7)
N1—C11—C12	121.97 (14)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O11^ii	0.83 (3)	1.82 (3)	2.6427 (16)	175 (3)
O4W—H4W···O14^iii	0.95 (2)	1.91 (2)	2.747 (2)	145.9 (19)

Symmetry codes: (ii) x−1/2, y−1/2, z; (iii) −x+1/2, y−1/2, −z+3/2.