The title compound, [Zn(C
7H
2NO
5)(H
2O)
3]·0.25CH
3CN·H
2O, was synthesized by the reaction of Zn(CH
3COO)
2·2H
2O 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.
Supporting information
CCDC reference: 225680
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
Crystal data top
[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) Å3 | Prism, pale yellow |
Z = 8 | 0.64 × 0.40 × 0.38 mm |
Data collection top
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 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1023P)2 + 10.2923P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—N22i | 1.333 (4) |
O15—H15 | 0.83 (3) | C21—C22i | 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—N22i | 175.9 (7) |
N1—C11—C12 | 121.97 (14) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O11ii | 0.83 (3) | 1.82 (3) | 2.6427 (16) | 175 (3) |
O4W—H4W···O14iii | 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. |