Download citation
Download citation
link to html
The Cu atom in the title complex, [Cu(C25H20N3O2)2(H2O)], has a distorted trigonal-bipyramidal coordination environment, with two O atoms of the pyrazolone rings and a water O atom in the equatorial plane and two N atoms in axial positions [N—Cu—N = 159.34 (16)°]. The complex occupies a special position on a twofold axis running through the Cu atom and the water O atom. The Cu—O(H2O) bond [2.549 (4) Å] is substantially longer than the rest of the bonds in the coordination polyhedron [Cu—O = 1.919 (2) Å and Cu—N = 1.990 (3) Å]. The pyrazolone ring is almost coplanar with the adjacent chelate ring, the dihedral angle formed by the mean plane of the pyrazolone ring and the planar part of the chelate ring being 2.91 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002496/ya6148sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002496/ya6148Isup2.hkl
Contains datablock I

CCDC reference: 206745

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • H-atom completeness 96%
  • R factor = 0.055
  • wR factor = 0.096
  • Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

Structure: I
------------

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_031 Alert C Refined Extinction Parameter within Range .... 2.67 Sigma PLAT_733 Alert C Torsion Calc -94.5(5), Rep -94.5(2) .... 2.50 su-Ratio N3 -CU1 -N3 -C21 2.556 1.555 1.555 1.555 General Notes
FORMU_01 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:C50 H42 Cu1 N6 O5 Atom count from the _atom_site data: C50 H40 Cu1 N6 O5 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C50 H42 Cu1 N6 O5 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 200.00 200.00 0.00 H 168.00 160.00 8.00 Cu 4.00 4.00 0.00 N 24.00 24.00 0.00 O 20.00 20.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
[Cu(C25H20N3O2)2(H2O)]F(000) = 1804
Mr = 870.35Dx = 1.359 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -c_2ycCell parameters from 790 reflections
a = 22.652 (6) Åθ = 2.3–20.9°
b = 16.228 (5) ŵ = 0.57 mm1
c = 15.250 (5) ÅT = 293 K
β = 130.636 (14)°Block, dark brown
V = 4254 (2) Å30.28 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2050 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.085
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
φ and ω scansh = 2625
8399 measured reflectionsk = 1719
3765 independent reflectionsl = 918
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055All H-atom parameters refined
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0266P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
3765 reflectionsΔρmax = 0.27 e Å3
362 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00032 (12)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.09200 (4)0.75000.0401 (2)
O10.09991 (13)0.05602 (14)0.6943 (2)0.0406 (7)
O20.40733 (17)0.17267 (19)1.2790 (3)0.0750 (10)
O30.00000.2490 (3)0.75000.1107 (19)
N10.20429 (16)0.08790 (18)0.6838 (3)0.0391 (7)
N20.21891 (19)0.12959 (18)0.7478 (3)0.0478 (9)
N30.03848 (16)0.11400 (16)0.9081 (2)0.0377 (8)
C10.1266 (2)0.0878 (2)0.7393 (3)0.0358 (9)
C20.0889 (2)0.1281 (2)0.8451 (3)0.0368 (9)
C30.1504 (2)0.1537 (2)0.8425 (4)0.0443 (10)
C40.1472 (4)0.2012 (5)0.9301 (6)0.0728 (17)
H410.131 (3)0.171 (3)0.988 (4)0.08 (2)*
H420.197 (2)0.220 (2)0.897 (4)0.084 (17)*
H430.115 (3)0.251 (3)0.956 (4)0.099 (19)*
C50.0068 (2)0.1357 (2)0.9301 (3)0.0368 (9)
C60.3683 (3)0.1221 (3)1.2788 (4)0.0589 (13)
C70.4042 (4)0.0625 (6)1.3743 (7)0.100 (3)
H710.385 (3)0.065 (3)1.411 (5)0.11 (2)*
H720.452 (3)0.067 (3)1.417 (4)0.088 (19)*
H730.400 (3)0.007 (3)1.354 (5)0.13 (3)*
C110.2661 (2)0.0499 (2)0.5792 (3)0.0402 (10)
C120.3402 (3)0.0829 (3)0.5114 (4)0.0542 (12)
H120.343 (2)0.130 (2)0.543 (3)0.052 (13)*
C130.4011 (3)0.0454 (4)0.4109 (5)0.0671 (14)
H130.451 (2)0.070 (2)0.369 (3)0.067 (14)*
C140.3895 (3)0.0247 (4)0.3758 (5)0.0816 (17)
H140.429 (2)0.046 (2)0.304 (4)0.069 (14)*
C150.3166 (3)0.0573 (4)0.4415 (5)0.0917 (19)
H150.307 (3)0.107 (3)0.418 (4)0.096 (18)*
C160.2551 (3)0.0209 (3)0.5427 (5)0.0707 (15)
H160.208 (2)0.045 (2)0.588 (3)0.062 (13)*
C210.1214 (2)0.1153 (2)1.0021 (3)0.0393 (10)
C220.1663 (3)0.1778 (3)1.0095 (4)0.0464 (11)
H220.1427 (19)0.219 (2)0.955 (3)0.044 (12)*
C230.2449 (3)0.1792 (3)1.0989 (4)0.0498 (12)
H230.2729 (19)0.221 (2)1.105 (3)0.041 (11)*
C240.2823 (2)0.1187 (2)1.1824 (3)0.0455 (10)
C250.2372 (3)0.0554 (3)1.1733 (4)0.0569 (12)
H250.260 (2)0.012 (2)1.224 (3)0.056 (13)*
C260.1581 (3)0.0540 (3)1.0834 (4)0.0528 (12)
H260.1270 (19)0.014 (2)1.074 (3)0.048 (12)*
C310.0281 (2)0.1687 (2)1.0465 (3)0.0385 (9)
C320.0365 (2)0.1214 (3)1.1283 (4)0.0490 (11)
H320.020 (2)0.066 (2)1.112 (3)0.057 (13)*
C330.0701 (3)0.1527 (4)1.2355 (4)0.0612 (13)
H330.122 (3)0.255 (3)1.342 (4)0.100 (16)*
C340.0953 (3)0.2324 (4)1.2616 (5)0.0783 (16)
H340.071 (2)0.117 (2)1.283 (3)0.070 (15)*
C350.0886 (3)0.2803 (4)1.1821 (5)0.0844 (18)
H350.105 (2)0.335 (3)1.195 (4)0.083 (16)*
C360.0553 (3)0.2490 (3)1.0747 (4)0.0613 (13)
H360.044 (2)0.278 (2)1.015 (3)0.068 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0367 (4)0.0523 (5)0.0338 (5)0.0000.0241 (4)0.000
O10.0370 (15)0.0500 (16)0.0376 (17)0.0061 (12)0.0256 (15)0.0079 (12)
O20.052 (2)0.091 (2)0.078 (3)0.0309 (18)0.041 (2)0.0203 (19)
O30.150 (5)0.071 (3)0.161 (6)0.0000.123 (5)0.000
N10.0343 (19)0.0456 (19)0.035 (2)0.0032 (17)0.0217 (18)0.0022 (18)
N20.050 (2)0.049 (2)0.056 (2)0.0067 (17)0.039 (2)0.0063 (18)
N30.0326 (18)0.049 (2)0.0333 (19)0.0104 (15)0.0221 (18)0.0074 (15)
C10.036 (2)0.032 (2)0.040 (2)0.001 (2)0.025 (2)0.004 (2)
C20.041 (2)0.035 (2)0.040 (3)0.0086 (18)0.029 (2)0.0060 (19)
C30.051 (3)0.043 (2)0.049 (3)0.007 (2)0.038 (3)0.007 (2)
C40.068 (4)0.089 (5)0.082 (5)0.006 (4)0.058 (4)0.018 (4)
C50.048 (3)0.032 (2)0.036 (2)0.0113 (19)0.030 (2)0.0016 (18)
C60.041 (3)0.083 (4)0.046 (3)0.014 (3)0.025 (3)0.017 (3)
C70.048 (4)0.145 (9)0.063 (5)0.009 (4)0.017 (4)0.019 (5)
C110.036 (3)0.044 (2)0.038 (3)0.004 (2)0.023 (2)0.003 (2)
C120.045 (3)0.060 (3)0.054 (3)0.001 (3)0.031 (3)0.004 (3)
C130.036 (3)0.093 (4)0.056 (4)0.005 (3)0.023 (3)0.009 (3)
C140.035 (3)0.124 (5)0.047 (4)0.013 (3)0.010 (3)0.020 (4)
C150.053 (4)0.097 (4)0.089 (5)0.012 (3)0.031 (4)0.049 (4)
C160.033 (3)0.069 (4)0.068 (4)0.001 (3)0.014 (3)0.019 (3)
C210.042 (2)0.049 (3)0.032 (2)0.013 (2)0.026 (2)0.011 (2)
C220.049 (3)0.047 (3)0.043 (3)0.011 (2)0.029 (3)0.000 (2)
C230.050 (3)0.054 (3)0.050 (3)0.026 (3)0.035 (3)0.012 (2)
C240.046 (3)0.055 (3)0.039 (3)0.013 (2)0.030 (2)0.006 (2)
C250.048 (3)0.064 (3)0.049 (3)0.009 (3)0.028 (3)0.010 (3)
C260.040 (3)0.063 (3)0.045 (3)0.017 (2)0.024 (3)0.006 (2)
C310.042 (2)0.040 (2)0.038 (3)0.010 (2)0.029 (2)0.008 (2)
C320.058 (3)0.051 (3)0.043 (3)0.008 (2)0.036 (3)0.001 (2)
C330.067 (3)0.080 (4)0.045 (3)0.005 (3)0.040 (3)0.004 (3)
C340.092 (4)0.088 (4)0.048 (4)0.024 (3)0.043 (4)0.026 (3)
C350.126 (5)0.065 (4)0.073 (4)0.036 (4)0.070 (4)0.030 (3)
C360.081 (4)0.059 (3)0.050 (3)0.017 (3)0.045 (3)0.008 (3)
Geometric parameters (Å, º) top
Cu1—O1i1.919 (2)C12—H120.93 (3)
Cu1—O11.919 (2)C13—C141.353 (7)
Cu1—N3i1.990 (3)C13—H130.95 (4)
Cu1—N31.990 (3)C14—C151.363 (7)
Cu1—O32.549 (4)C14—H140.92 (4)
O1—C11.282 (4)C15—C161.368 (6)
O2—C61.205 (4)C15—H150.95 (4)
N1—C11.368 (4)C16—H160.90 (4)
N1—N21.393 (4)C21—C261.370 (5)
N1—C111.406 (4)C21—C221.387 (5)
N2—C31.314 (5)C22—C231.368 (6)
N3—C51.319 (4)C22—H220.91 (3)
N3—C211.441 (4)C23—C241.378 (5)
C1—C21.401 (5)C23—H230.89 (3)
C2—C51.419 (5)C24—C251.390 (5)
C2—C31.429 (5)C25—C261.375 (6)
C3—C41.504 (6)C25—H250.92 (3)
C4—H410.86 (4)C26—H260.90 (3)
C4—H420.93 (4)C31—C321.370 (5)
C4—H430.98 (5)C31—C361.385 (5)
C5—C311.494 (5)C32—C331.375 (6)
C6—C71.475 (8)C32—H320.94 (3)
C6—C241.493 (5)C33—C341.364 (6)
C7—H710.91 (5)C33—H340.92 (4)
C7—H720.83 (4)C34—C351.364 (7)
C7—H730.93 (5)C34—H331.02 (4)
C11—C161.368 (5)C35—C361.378 (6)
C11—C121.382 (5)C35—H350.94 (4)
C12—C131.367 (6)C36—H360.90 (4)
O1i—Cu1—O1144.56 (14)C14—C13—C12120.3 (5)
O1i—Cu1—N3i92.89 (10)C14—C13—H13123 (2)
O1—Cu1—N3i93.37 (11)C12—C13—H13117 (2)
O1—Cu1—O3107.72 (12)C13—C14—C15119.3 (5)
N3—Cu1—O3i79.67 (9)C13—C14—H14120 (3)
O1i—Cu1—N393.37 (11)C15—C14—H14120 (3)
O1—Cu1—N392.89 (10)C14—C15—C16121.2 (6)
N3i—Cu1—N3159.34 (16)C14—C15—H15120 (3)
C1—O1—Cu1118.2 (2)C16—C15—H15118 (3)
C1—N1—N2111.3 (3)C15—C16—C11120.1 (5)
C1—N1—C11129.1 (3)C15—C16—H16120 (3)
N2—N1—C11119.5 (3)C11—C16—H16119 (3)
C3—N2—N1105.3 (3)C26—C21—C22118.5 (4)
C5—N3—C21118.0 (3)C26—C21—N3121.3 (3)
C5—N3—Cu1123.8 (2)C22—C21—N3120.2 (4)
C21—N3—Cu1117.8 (2)C23—C22—C21120.2 (4)
O1—C1—N1122.3 (3)C23—C22—H22120 (2)
O1—C1—C2131.0 (3)C21—C22—H22119 (2)
N1—C1—C2106.7 (3)C22—C23—C24121.8 (4)
C1—C2—C5123.2 (3)C22—C23—H23120 (2)
C1—C2—C3104.5 (3)C24—C23—H23119 (2)
C5—C2—C3132.3 (4)C23—C24—C25117.7 (4)
N2—C3—C2112.1 (3)C23—C24—C6120.4 (4)
N2—C3—C4117.9 (4)C25—C24—C6122.0 (4)
C2—C3—C4130.0 (4)C26—C25—C24120.6 (4)
C3—C4—H41111 (3)C26—C25—H25118 (2)
C3—C4—H42110 (3)C24—C25—H25121 (2)
H41—C4—H42108 (4)C21—C26—C25121.2 (4)
C3—C4—H43112 (3)C21—C26—H26116 (2)
H41—C4—H43111 (5)C25—C26—H26123 (2)
H42—C4—H43106 (4)C32—C31—C36118.4 (4)
N3—C5—C2121.2 (3)C32—C31—C5122.3 (4)
N3—C5—C31120.0 (3)C36—C31—C5119.3 (4)
C2—C5—C31118.8 (3)C31—C32—C33121.1 (5)
O2—C6—C7120.8 (5)C31—C32—H32120 (2)
O2—C6—C24120.8 (4)C33—C32—H32119 (2)
C7—C6—C24118.3 (5)C34—C33—C32120.0 (5)
C6—C7—H71114 (4)C34—C33—H34125 (3)
C6—C7—H72108 (3)C32—C33—H34115 (3)
H71—C7—H72115 (5)C33—C34—C35119.8 (5)
C6—C7—H73116 (4)C33—C34—H33120 (3)
H71—C7—H73106 (5)C35—C34—H33120 (3)
H72—C7—H7398 (5)C34—C35—C36120.3 (5)
C16—C11—C12118.3 (4)C34—C35—H35124 (3)
C16—C11—N1121.3 (4)C36—C35—H35116 (3)
C12—C11—N1120.4 (4)C35—C36—C31120.3 (5)
C13—C12—C11120.9 (5)C35—C36—H36125 (3)
C13—C12—H12126 (2)C31—C36—H36114 (3)
C11—C12—H12113 (2)
O1i—Cu1—O1—C1130.6 (2)C16—C11—C12—C130.6 (6)
N3i—Cu1—O1—C1129.6 (2)N1—C11—C12—C13178.4 (4)
N3—Cu1—O1—C130.7 (3)C11—C12—C13—C140.4 (7)
C1—N1—N2—C30.8 (4)C12—C13—C14—C150.3 (8)
C11—N1—N2—C3176.4 (3)C13—C14—C15—C160.8 (9)
O1i—Cu1—N3—C5174.4 (3)C14—C15—C16—C110.6 (9)
O1—Cu1—N3—C529.3 (3)C12—C11—C16—C150.1 (7)
N3i—Cu1—N3—C578.2 (3)N1—C11—C16—C15178.9 (4)
O1i—Cu1—N3—C2112.9 (3)C5—N3—C21—C2677.3 (4)
O1—Cu1—N3—C21158.0 (2)Cu1—N3—C21—C26109.6 (3)
N3i—Cu1—N3—C2194.5 (2)C5—N3—C21—C22105.1 (4)
Cu1—O1—C1—N1158.2 (3)Cu1—N3—C21—C2268.1 (4)
Cu1—O1—C1—C220.7 (5)C26—C21—C22—C232.5 (5)
N2—N1—C1—O1177.0 (3)N3—C21—C22—C23179.8 (3)
C11—N1—C1—O16.2 (6)C21—C22—C23—C241.5 (6)
N2—N1—C1—C22.2 (4)C22—C23—C24—C250.3 (6)
C11—N1—C1—C2174.7 (3)C22—C23—C24—C6180.0 (4)
O1—C1—C2—C54.8 (6)O2—C6—C24—C237.7 (6)
N1—C1—C2—C5176.1 (3)C7—C6—C24—C23171.9 (6)
O1—C1—C2—C3176.5 (4)O2—C6—C24—C25172.5 (4)
N1—C1—C2—C32.6 (4)C7—C6—C24—C257.9 (7)
N1—N2—C3—C20.9 (4)C23—C24—C25—C260.2 (6)
N1—N2—C3—C4180.0 (4)C6—C24—C25—C26180.0 (4)
C1—C2—C3—N22.2 (4)C22—C21—C26—C252.5 (6)
C5—C2—C3—N2176.3 (4)N3—C21—C26—C25179.8 (4)
C1—C2—C3—C4178.8 (5)C24—C25—C26—C211.4 (7)
C5—C2—C3—C42.7 (8)N3—C5—C31—C32101.6 (4)
C21—N3—C5—C2173.6 (3)C2—C5—C31—C3278.1 (5)
Cu1—N3—C5—C213.7 (4)N3—C5—C31—C3676.4 (5)
C21—N3—C5—C316.1 (5)C2—C5—C31—C36103.9 (4)
Cu1—N3—C5—C31166.6 (2)C36—C31—C32—C330.8 (6)
C1—C2—C5—N38.6 (5)C5—C31—C32—C33178.8 (4)
C3—C2—C5—N3173.1 (3)C31—C32—C33—C340.5 (7)
C1—C2—C5—C31171.1 (3)C32—C33—C34—C351.5 (8)
C3—C2—C5—C317.2 (6)C33—C34—C35—C361.2 (9)
C1—N1—C11—C1629.3 (6)C34—C35—C36—C310.2 (8)
N2—N1—C11—C16147.4 (4)C32—C31—C36—C351.1 (7)
C1—N1—C11—C12151.7 (4)C5—C31—C36—C35179.2 (4)
N2—N1—C11—C1231.7 (5)
Symmetry code: (i) x, y, z+3/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds