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The title compound, [Zn(C20H18N2O6)]·CH3OH, has been synthesized through a one-step procedure in a methanol solvent. The Zn atom exhibits a distorted trigonal prismatic geometry consisting of two imine N-atom donors, two O-atom donors of the phen­oxy groups and two O-atom donors of the deprotonated carboxyl groups. C—H...O inter­actions stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026791/hy2007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026791/hy2007Isup2.hkl
Contains datablock I

CCDC reference: 274148

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.048
  • wR factor = 0.070
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 2.39 PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 3 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT350_ALERT_3_C Short C-H Bond (0.96A) C21 - H21A ... 0.84 Ang. PLAT391_ALERT_3_C Deviating Methyl C21 H-C-H Bond Angle ...... 118.00 Deg.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 2.391 Tmax scaled 0.727 Tmin scaled 0.641
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

{2,2'-[Ethane-1,2-diylbisnitrilomethylidyne)]diphenoxyacetato}zinc(II) methanol solvate top
Crystal data top
[Zn(C20H18N2O6)]·CH4OF(000) = 992
Mr = 479.78Dx = 1.532 Mg m3
Monoclinic, P21/cMelting point: not measured K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.200 (2) ÅCell parameters from 11738 reflections
b = 18.274 (5) Åθ = 1.8–26.1°
c = 14.191 (4) ŵ = 1.23 mm1
β = 101.974 (5)°T = 293 K
V = 2080.1 (10) Å3Block, colorless
Z = 40.45 × 0.33 × 0.26 mm
Data collection top
Bruker SMART area-detector
diffractometer
4073 independent reflections
Radiation source: fine-focus sealed tube2426 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
φ and ω scansθmax = 26.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.268, Tmax = 0.304k = 2219
11533 measured reflectionsl = 1714
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0113P)2]
where P = (Fo2 + 2Fc2)/3
4073 reflections(Δ/σ)max = 0.001
296 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.36 e Å3
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
C10.8741 (4)0.58214 (18)0.3839 (3)0.0363 (9)
C20.9436 (4)0.59396 (16)0.4902 (2)0.0437 (10)
H2A0.89870.55770.52780.052*
H2B1.06400.58930.50390.052*
C30.9477 (4)0.68950 (19)0.6066 (2)0.0387 (9)
C41.0407 (4)0.64762 (19)0.6792 (3)0.0511 (10)
H41.06970.59990.66690.061*
C51.0903 (5)0.6770 (2)0.7700 (3)0.0579 (12)
H51.15250.64870.81890.069*
C61.0498 (5)0.7469 (2)0.7893 (3)0.0587 (11)
H61.08250.76590.85110.070*
C70.9602 (5)0.7893 (2)0.7164 (3)0.0542 (11)
H70.93570.83750.72930.065*
C80.9053 (4)0.76148 (19)0.6237 (3)0.0415 (10)
C90.8126 (4)0.81176 (19)0.5518 (3)0.0486 (10)
H90.81810.86120.56750.058*
C100.6398 (5)0.85461 (17)0.4098 (3)0.0607 (11)
H10A0.70260.89970.42420.073*
H10B0.52940.86200.42270.073*
C110.6274 (5)0.83382 (19)0.3057 (3)0.0614 (12)
H11A0.56110.86960.26390.074*
H11B0.73760.83220.29080.074*
C120.4580 (5)0.7475 (2)0.2080 (3)0.0535 (11)
H120.44910.78490.16270.064*
C130.3677 (4)0.6807 (2)0.1760 (3)0.0463 (10)
C140.3032 (5)0.6743 (2)0.0774 (3)0.0675 (13)
H140.31970.71220.03660.081*
C150.2157 (5)0.6133 (3)0.0392 (3)0.0745 (14)
H150.17700.60910.02700.089*
C160.1862 (5)0.5587 (2)0.0997 (3)0.0683 (13)
H160.12550.51770.07440.082*
C170.2458 (4)0.5638 (2)0.1982 (3)0.0552 (11)
H170.22440.52650.23850.066*
C180.3368 (4)0.6243 (2)0.2367 (3)0.0417 (9)
C190.3648 (4)0.57910 (17)0.3991 (2)0.0458 (10)
H19A0.42240.53450.38850.055*
H19B0.24660.56850.38960.055*
C200.4294 (5)0.6068 (2)0.5003 (3)0.0467 (10)
C210.6468 (8)0.5110 (5)0.1450 (6)0.0838 (19)
N10.7252 (4)0.79432 (14)0.4700 (2)0.0479 (8)
N20.5483 (4)0.76137 (16)0.2909 (2)0.0461 (8)
O10.8973 (3)0.66543 (11)0.51419 (16)0.0464 (7)
O20.9454 (3)0.53682 (11)0.34253 (17)0.0469 (7)
O30.7490 (3)0.62015 (11)0.34458 (16)0.0433 (6)
O40.3930 (3)0.63453 (11)0.33277 (17)0.0449 (6)
O50.3814 (3)0.57506 (14)0.56578 (19)0.0697 (8)
O60.5325 (3)0.65986 (12)0.51064 (16)0.0512 (7)
O70.8187 (4)0.50995 (14)0.1495 (2)0.0654 (9)
Zn10.63891 (5)0.69486 (2)0.40859 (3)0.04183 (14)
H21A0.611 (7)0.554 (3)0.148 (4)0.15 (3)*
H21B0.602 (6)0.497 (2)0.088 (3)0.11 (2)*
H21C0.632 (6)0.478 (2)0.193 (3)0.12 (2)*
H7O0.862 (5)0.516 (2)0.213 (3)0.109 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.044 (2)0.028 (2)0.037 (2)0.0038 (18)0.0101 (19)0.0009 (17)
C20.055 (2)0.034 (2)0.042 (3)0.0127 (19)0.010 (2)0.0006 (17)
C30.046 (2)0.036 (2)0.034 (2)0.0021 (19)0.0081 (18)0.0077 (19)
C40.058 (3)0.047 (2)0.047 (3)0.007 (2)0.007 (2)0.005 (2)
C50.066 (3)0.069 (3)0.036 (3)0.001 (2)0.004 (2)0.001 (2)
C60.069 (3)0.063 (3)0.044 (3)0.007 (2)0.013 (2)0.015 (2)
C70.055 (3)0.049 (3)0.061 (3)0.007 (2)0.019 (2)0.016 (2)
C80.041 (2)0.037 (2)0.047 (3)0.0024 (18)0.0096 (19)0.0086 (19)
C90.053 (3)0.030 (2)0.066 (3)0.002 (2)0.020 (2)0.008 (2)
C100.062 (3)0.032 (2)0.086 (3)0.010 (2)0.011 (2)0.003 (2)
C110.058 (3)0.046 (3)0.080 (4)0.008 (2)0.014 (3)0.019 (2)
C120.049 (3)0.063 (3)0.051 (3)0.017 (2)0.017 (2)0.023 (2)
C130.043 (2)0.060 (3)0.038 (3)0.009 (2)0.0115 (19)0.004 (2)
C140.070 (3)0.091 (4)0.042 (3)0.016 (3)0.014 (2)0.010 (2)
C150.078 (4)0.109 (4)0.035 (3)0.007 (3)0.009 (3)0.006 (3)
C160.061 (3)0.090 (4)0.051 (3)0.006 (3)0.004 (3)0.024 (3)
C170.052 (3)0.065 (3)0.047 (3)0.004 (2)0.006 (2)0.003 (2)
C180.036 (2)0.059 (3)0.031 (2)0.008 (2)0.0096 (18)0.002 (2)
C190.048 (2)0.049 (2)0.041 (3)0.0071 (19)0.011 (2)0.0039 (19)
C200.044 (3)0.056 (3)0.041 (3)0.010 (2)0.011 (2)0.005 (2)
C210.067 (4)0.091 (6)0.088 (6)0.017 (4)0.003 (4)0.015 (4)
N10.049 (2)0.037 (2)0.056 (2)0.0079 (16)0.0053 (17)0.0026 (16)
N20.045 (2)0.047 (2)0.048 (2)0.0075 (16)0.0119 (17)0.0116 (16)
O10.0595 (17)0.0351 (15)0.0396 (17)0.0123 (12)0.0010 (13)0.0071 (11)
O20.0570 (17)0.0436 (15)0.0397 (17)0.0115 (13)0.0092 (13)0.0090 (12)
O30.0472 (16)0.0389 (15)0.0412 (16)0.0082 (12)0.0035 (13)0.0037 (11)
O40.0524 (16)0.0468 (15)0.0343 (16)0.0011 (13)0.0065 (13)0.0085 (12)
O50.078 (2)0.092 (2)0.043 (2)0.0104 (17)0.0201 (16)0.0162 (15)
O60.0625 (18)0.0513 (16)0.0411 (17)0.0059 (14)0.0143 (14)0.0036 (12)
O70.061 (2)0.083 (2)0.051 (2)0.0019 (17)0.0095 (17)0.0107 (16)
Zn10.0444 (3)0.0363 (2)0.0444 (3)0.0046 (2)0.00847 (19)0.0032 (2)
Geometric parameters (Å, º) top
C1—O21.231 (4)C12—H120.9300
C1—O31.268 (3)C13—C141.394 (5)
C1—C21.512 (4)C13—C181.399 (4)
C2—O11.421 (3)C14—C151.376 (5)
C2—H2A0.9700C14—H140.9300
C2—H2B0.9700C15—C161.370 (5)
C3—O11.363 (4)C15—H150.9300
C3—C41.379 (4)C16—C171.384 (5)
C3—C81.395 (4)C16—H160.9300
C4—C51.377 (4)C17—C181.382 (4)
C4—H40.9300C17—H170.9300
C5—C61.362 (4)C18—O41.358 (4)
C5—H50.9300C19—O41.434 (3)
C6—C71.376 (4)C19—C201.510 (4)
C6—H60.9300C19—H19A0.9700
C7—C81.396 (4)C19—H19B0.9700
C7—H70.9300C20—O51.228 (4)
C8—C91.463 (4)C20—O61.275 (4)
C9—N11.272 (4)C21—O71.398 (6)
C9—H90.9300C21—H21A0.85 (5)
C10—N11.478 (4)C21—H21B0.85 (4)
C10—C111.508 (5)C21—H21C0.94 (4)
C10—H10A0.9700N1—Zn12.075 (3)
C10—H10B0.9700N2—Zn12.074 (3)
C11—N21.470 (4)O1—Zn12.389 (2)
C11—H11A0.9700O3—Zn11.961 (2)
C11—H11B0.9700O4—Zn12.353 (2)
C12—N21.278 (4)O6—Zn11.947 (3)
C12—C131.452 (5)O7—H7O0.91 (4)
O2—C1—O3125.4 (3)C15—C16—C17120.9 (4)
O2—C1—C2117.0 (3)C15—C16—H16119.6
O3—C1—C2117.6 (3)C17—C16—H16119.6
O1—C2—C1107.8 (3)C16—C17—C18120.1 (4)
O1—C2—H2A110.1C16—C17—H17119.9
C1—C2—H2A110.1C18—C17—H17119.9
O1—C2—H2B110.1O4—C18—C17123.4 (3)
C1—C2—H2B110.1O4—C18—C13116.7 (3)
H2A—C2—H2B108.5C17—C18—C13119.8 (4)
O1—C3—C4123.3 (3)O4—C19—C20108.3 (3)
O1—C3—C8115.8 (3)O4—C19—H19A110.0
C4—C3—C8120.8 (3)C20—C19—H19A110.0
C5—C4—C3119.5 (3)O4—C19—H19B110.0
C5—C4—H4120.3C20—C19—H19B110.0
C3—C4—H4120.3H19A—C19—H19B108.4
C6—C5—C4121.2 (4)O5—C20—O6125.5 (4)
C6—C5—H5119.4O5—C20—C19117.2 (4)
C4—C5—H5119.4O6—C20—C19117.3 (3)
C5—C6—C7119.4 (4)O7—C21—H21A111 (4)
C5—C6—H6120.3O7—C21—H21B106 (3)
C7—C6—H6120.3H21A—C21—H21B104 (5)
C6—C7—C8121.4 (4)O7—C21—H21C104 (3)
C6—C7—H7119.3H21A—C21—H21C118 (5)
C8—C7—H7119.3H21B—C21—H21C114 (4)
C3—C8—C7117.7 (3)C9—N1—C10116.7 (3)
C3—C8—C9125.7 (3)C9—N1—Zn1132.9 (3)
C7—C8—C9116.6 (3)C10—N1—Zn1109.3 (2)
N1—C9—C8126.3 (3)C12—N2—C11117.6 (3)
N1—C9—H9116.9C12—N2—Zn1131.9 (3)
C8—C9—H9116.9C11—N2—Zn1109.8 (2)
N1—C10—C11107.8 (3)C3—O1—C2119.0 (3)
N1—C10—H10A110.2C3—O1—Zn1125.7 (2)
C11—C10—H10A110.2C2—O1—Zn1107.62 (18)
N1—C10—H10B110.2C1—O3—Zn1125.8 (2)
C11—C10—H10B110.2C18—O4—C19119.6 (3)
H10A—C10—H10B108.5C18—O4—Zn1127.1 (2)
N2—C11—C10107.8 (3)C19—O4—Zn1105.69 (19)
N2—C11—H11A110.2C20—O6—Zn1123.5 (2)
C10—C11—H11A110.2C21—O7—H7O103 (3)
N2—C11—H11B110.2O6—Zn1—O3115.86 (9)
C10—C11—H11B110.2O6—Zn1—N198.17 (11)
H11A—C11—H11B108.5O3—Zn1—N1130.87 (11)
N2—C12—C13127.9 (4)O6—Zn1—N2130.56 (11)
N2—C12—H12116.0O3—Zn1—N299.06 (11)
C13—C12—H12116.0N1—Zn1—N281.87 (12)
C14—C13—C18118.5 (4)O6—Zn1—O473.30 (9)
C14—C13—C12116.5 (4)O3—Zn1—O483.98 (9)
C18—C13—C12124.9 (4)N1—Zn1—O4141.94 (10)
C15—C14—C13121.4 (4)N2—Zn1—O477.09 (10)
C15—C14—H14119.3O6—Zn1—O186.29 (9)
C13—C14—H14119.3O3—Zn1—O172.55 (9)
C16—C15—C14119.2 (4)N1—Zn1—O175.70 (9)
C16—C15—H15120.4N2—Zn1—O1139.46 (10)
C14—C15—H15120.4O4—Zn1—O1138.21 (7)
O2—C1—C2—O1155.3 (3)O5—C20—O6—Zn1167.0 (3)
O3—C1—C2—O123.9 (4)C19—C20—O6—Zn111.1 (4)
O1—C3—C4—C5178.2 (3)C20—O6—Zn1—O351.6 (3)
C8—C3—C4—C50.9 (6)C20—O6—Zn1—N1164.9 (3)
C3—C4—C5—C60.3 (6)C20—O6—Zn1—N278.6 (3)
C4—C5—C6—C71.1 (6)C20—O6—Zn1—O422.9 (2)
C5—C6—C7—C82.0 (6)C20—O6—Zn1—O1120.1 (3)
O1—C3—C8—C7177.5 (3)C1—O3—Zn1—O664.3 (3)
C4—C3—C8—C70.0 (5)C1—O3—Zn1—N164.6 (3)
O1—C3—C8—C90.2 (5)C1—O3—Zn1—N2151.7 (3)
C4—C3—C8—C9177.7 (3)C1—O3—Zn1—O4132.4 (3)
C6—C7—C8—C31.4 (6)C1—O3—Zn1—O112.5 (2)
C6—C7—C8—C9179.4 (3)C9—N1—Zn1—O652.7 (4)
C3—C8—C9—N116.8 (6)C10—N1—Zn1—O6115.1 (2)
C7—C8—C9—N1165.4 (4)C9—N1—Zn1—O382.3 (4)
N1—C10—C11—N253.5 (4)C10—N1—Zn1—O3110.0 (2)
N2—C12—C13—C14168.7 (4)C9—N1—Zn1—N2177.3 (4)
N2—C12—C13—C1813.6 (6)C10—N1—Zn1—N215.0 (2)
C18—C13—C14—C152.2 (6)C9—N1—Zn1—O4126.0 (3)
C12—C13—C14—C15179.9 (4)C10—N1—Zn1—O441.8 (3)
C13—C14—C15—C162.4 (6)C9—N1—Zn1—O131.3 (3)
C14—C15—C16—C171.1 (7)C10—N1—Zn1—O1160.9 (3)
C15—C16—C17—C180.3 (6)C12—N2—Zn1—O682.1 (4)
C16—C17—C18—O4177.1 (3)C11—N2—Zn1—O6108.1 (2)
C16—C17—C18—C130.5 (5)C12—N2—Zn1—O353.8 (4)
C14—C13—C18—O4176.1 (3)C11—N2—Zn1—O3116.0 (2)
C12—C13—C18—O41.6 (5)C12—N2—Zn1—N1175.9 (4)
C14—C13—C18—C170.7 (5)C11—N2—Zn1—N114.2 (2)
C12—C13—C18—C17178.4 (3)C12—N2—Zn1—O427.9 (3)
O4—C19—C20—O5163.1 (3)C11—N2—Zn1—O4162.3 (2)
O4—C19—C20—O618.7 (4)C12—N2—Zn1—O1127.5 (3)
C8—C9—N1—C10178.9 (3)C11—N2—Zn1—O142.3 (3)
C8—C9—N1—Zn111.8 (6)C18—O4—Zn1—O6178.6 (3)
C11—C10—N1—C9149.2 (3)C19—O4—Zn1—O629.7 (2)
C11—C10—N1—Zn140.8 (3)C18—O4—Zn1—O359.3 (2)
C13—C12—N2—C11180.0 (3)C19—O4—Zn1—O389.6 (2)
C13—C12—N2—Zn110.8 (6)C18—O4—Zn1—N199.6 (3)
C10—C11—N2—C12148.3 (3)C19—O4—Zn1—N1111.5 (2)
C10—C11—N2—Zn140.2 (3)C18—O4—Zn1—N241.4 (2)
C4—C3—O1—C20.7 (5)C19—O4—Zn1—N2169.7 (2)
C8—C3—O1—C2176.7 (3)C18—O4—Zn1—O1114.6 (2)
C4—C3—O1—Zn1144.7 (3)C19—O4—Zn1—O134.4 (3)
C8—C3—O1—Zn137.9 (4)C3—O1—Zn1—O653.8 (3)
C1—C2—O1—C3179.1 (3)C2—O1—Zn1—O694.8 (2)
C1—C2—O1—Zn129.8 (3)C3—O1—Zn1—O3172.4 (3)
O2—C1—O3—Zn1177.8 (2)C2—O1—Zn1—O323.81 (19)
C2—C1—O3—Zn11.3 (4)C3—O1—Zn1—N145.6 (3)
C17—C18—O4—C193.0 (5)C2—O1—Zn1—N1165.8 (2)
C13—C18—O4—C19179.7 (3)C3—O1—Zn1—N2104.1 (3)
C17—C18—O4—Zn1148.1 (3)C2—O1—Zn1—N2107.3 (2)
C13—C18—O4—Zn135.2 (4)C3—O1—Zn1—O4113.5 (2)
C20—C19—O4—C18176.3 (3)C2—O1—Zn1—O435.1 (3)
C20—C19—O4—Zn132.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7O···O20.91 (4)1.86 (4)2.764 (4)174 (4)
 

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