The title compound, [Cu(ClO4)2(C6H6N2O2)2], contains neutral molecules of a centrosymmetric mononuclear copper(II) complex, in which the zwitterionic hydroxamic acid ligand is O,O′-chelated to the CuII atom. The CuII atom lies on an inversion centre and has a distorted tetragonal-bipyramidal environment, being coordinated by four O atoms of the two N-hydroxynicotinamide molecules forming the equatorial plane, and by two O atoms of the perchlorate anions occupying the axial positions.
Supporting information
CCDC reference: 647200
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.032
- wR factor = 0.091
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cl1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C5 .. 3.00 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C6 .. O4 .. 2.92 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2003b); software used to prepare material for publication: SHELXL97.
Bis(
N-hydroxynicotinamidium-
κ2O,
O')diperchloratocopper(II)
top
Crystal data top
[Cu(ClO4)2(C6H6N2O2)2] | F(000) = 1084 |
Mr = 538.70 | Dx = 1.985 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6668 reflections |
a = 14.1287 (7) Å | θ = 1.0–27.5° |
b = 8.6553 (3) Å | µ = 1.59 mm−1 |
c = 15.7370 (8) Å | T = 120 K |
β = 110.535 (2)° | Block, green |
V = 1802.17 (14) Å3 | 0.23 × 0.15 × 0.12 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2057 independent reflections |
Radiation source: fine-focus sealed tube | 1746 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.037 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
φ scans, and ω scans with κ offset | h = −18→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003a) | k = −11→11 |
Tmin = 0.710, Tmax = 0.832 | l = −20→19 |
10729 measured reflections | |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.053P)2 + 2.0829P] where P = (Fo2 + 2Fc2)/3 |
2057 reflections | (Δ/σ)max < 0.001 |
178 parameters | Δρmax = 0.46 e Å−3 |
3 restraints | Δρmin = −0.63 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) |
Cu1 | 0.2500 | 0.7500 | 0.5000 | 0.01757 (14) | |
Cl1 | −0.03389 (4) | 0.76488 (5) | 0.40513 (4) | 0.02137 (16) | |
O1 | 0.27029 (11) | 0.88460 (16) | 0.60226 (9) | 0.0197 (3) | |
O2 | 0.29805 (11) | 0.92226 (15) | 0.44917 (9) | 0.0190 (3) | |
O3 | 0.05127 (13) | 0.8602 (2) | 0.41080 (13) | 0.0376 (4) | |
O4 | −0.0112 (15) | 0.6128 (14) | 0.3842 (13) | 0.038 (3) | 0.48 (4) |
O5 | −0.1253 (9) | 0.819 (2) | 0.3407 (12) | 0.043 (3) | 0.48 (4) |
O6 | −0.0343 (14) | 0.7627 (19) | 0.4973 (6) | 0.037 (3) | 0.48 (4) |
O4B | −0.0174 (14) | 0.6030 (11) | 0.4091 (13) | 0.039 (3) | 0.52 (4) |
O5B | −0.1136 (11) | 0.799 (2) | 0.3198 (8) | 0.041 (2) | 0.52 (4) |
O6B | −0.0794 (17) | 0.8070 (14) | 0.4730 (12) | 0.047 (4) | 0.52 (4) |
N1 | 0.32457 (13) | 1.03670 (19) | 0.51363 (11) | 0.0167 (3) | |
H1N | 0.360 (2) | 1.110 (3) | 0.5040 (17) | 0.027 (6)* | |
N2 | 0.36369 (13) | 1.1779 (2) | 0.81671 (11) | 0.0178 (3) | |
H2N | 0.3600 (19) | 1.147 (3) | 0.8662 (18) | 0.029 (7)* | |
C1 | 0.30986 (14) | 1.0108 (2) | 0.59012 (13) | 0.0162 (4) | |
C2 | 0.33853 (14) | 1.1282 (2) | 0.66305 (13) | 0.0160 (4) | |
C3 | 0.35754 (16) | 1.2836 (2) | 0.65181 (14) | 0.0185 (4) | |
H3 | 0.3556 | 1.3205 | 0.5944 | 0.022* | |
C4 | 0.37929 (15) | 1.3842 (2) | 0.72515 (15) | 0.0203 (4) | |
H4 | 0.3922 | 1.4903 | 0.7182 | 0.024* | |
C5 | 0.38190 (15) | 1.3281 (2) | 0.80821 (14) | 0.0196 (4) | |
H5 | 0.3965 | 1.3955 | 0.8589 | 0.024* | |
C6 | 0.34182 (14) | 1.0780 (2) | 0.74764 (13) | 0.0178 (4) | |
H6 | 0.3286 | 0.9728 | 0.7566 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0231 (2) | 0.0171 (2) | 0.0166 (2) | −0.00409 (12) | 0.01207 (16) | −0.00280 (12) |
Cl1 | 0.0266 (3) | 0.0175 (3) | 0.0242 (3) | −0.00120 (17) | 0.0143 (2) | 0.00224 (17) |
O1 | 0.0255 (7) | 0.0182 (7) | 0.0192 (7) | −0.0051 (6) | 0.0128 (6) | −0.0028 (5) |
O2 | 0.0247 (7) | 0.0182 (7) | 0.0172 (7) | −0.0050 (6) | 0.0110 (6) | −0.0046 (5) |
O3 | 0.0312 (9) | 0.0339 (9) | 0.0533 (11) | −0.0089 (7) | 0.0218 (8) | −0.0009 (8) |
O4 | 0.030 (4) | 0.024 (3) | 0.046 (7) | 0.004 (3) | −0.003 (4) | −0.010 (3) |
O5 | 0.016 (2) | 0.039 (5) | 0.072 (6) | 0.014 (2) | 0.013 (4) | 0.024 (5) |
O6 | 0.045 (6) | 0.050 (5) | 0.022 (3) | −0.024 (4) | 0.019 (3) | −0.007 (2) |
O4B | 0.031 (3) | 0.019 (2) | 0.058 (7) | 0.0050 (17) | 0.002 (5) | 0.011 (3) |
O5B | 0.036 (4) | 0.032 (4) | 0.055 (4) | 0.007 (3) | 0.013 (3) | 0.014 (3) |
O6B | 0.066 (8) | 0.047 (4) | 0.045 (5) | −0.020 (4) | 0.042 (6) | −0.016 (3) |
N1 | 0.0184 (8) | 0.0168 (8) | 0.0176 (8) | −0.0024 (6) | 0.0098 (7) | −0.0024 (6) |
N2 | 0.0211 (9) | 0.0193 (8) | 0.0154 (8) | −0.0011 (7) | 0.0094 (7) | −0.0001 (7) |
C1 | 0.0157 (9) | 0.0164 (9) | 0.0176 (9) | 0.0021 (7) | 0.0073 (7) | 0.0008 (7) |
C2 | 0.0152 (9) | 0.0179 (9) | 0.0163 (10) | 0.0016 (7) | 0.0072 (7) | −0.0002 (7) |
C3 | 0.0188 (10) | 0.0202 (9) | 0.0193 (10) | 0.0010 (8) | 0.0102 (8) | 0.0016 (8) |
C4 | 0.0211 (10) | 0.0171 (9) | 0.0261 (10) | −0.0006 (8) | 0.0126 (8) | −0.0007 (8) |
C5 | 0.0196 (10) | 0.0185 (10) | 0.0222 (10) | −0.0009 (8) | 0.0093 (8) | −0.0037 (8) |
C6 | 0.0182 (10) | 0.0167 (9) | 0.0208 (10) | −0.0010 (7) | 0.0098 (8) | −0.0008 (7) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9250 (13) | N1—C1 | 1.311 (3) |
Cu1—O1i | 1.9250 (13) | N1—H1N | 0.86 (3) |
Cu1—O2 | 1.9248 (14) | N2—C6 | 1.337 (3) |
Cu1—O2i | 1.9248 (14) | N2—C5 | 1.341 (3) |
Cu1—O3 | 2.8282 (18) | N2—H2N | 0.84 (3) |
Cl1—O5 | 1.412 (10) | C1—C2 | 1.479 (3) |
Cl1—O4B | 1.418 (9) | C2—C6 | 1.385 (3) |
Cl1—O4 | 1.420 (10) | C2—C3 | 1.395 (3) |
Cl1—O3 | 1.4356 (16) | C3—C4 | 1.391 (3) |
Cl1—O5B | 1.449 (10) | C3—H3 | 0.9500 |
Cl1—O6 | 1.453 (5) | C4—C5 | 1.383 (3) |
Cl1—O6B | 1.473 (6) | C4—H4 | 0.9500 |
O1—C1 | 1.272 (2) | C5—H5 | 0.9500 |
O2—N1 | 1.373 (2) | C6—H6 | 0.9500 |
| | | |
O2—Cu1—O2i | 180.00 (5) | C1—N1—H1N | 125.5 (17) |
O2—Cu1—O1 | 84.71 (6) | O2—N1—H1N | 115.6 (17) |
O2i—Cu1—O1 | 95.29 (6) | C6—N2—C5 | 122.90 (18) |
O2—Cu1—O1i | 95.29 (6) | C6—N2—H2N | 118.2 (18) |
O2i—Cu1—O1i | 84.71 (6) | C5—N2—H2N | 118.6 (18) |
O1—Cu1—O1i | 180.0 | O1—C1—N1 | 120.31 (17) |
O2—Cu1—O3 | 88.05 (5) | O1—C1—C2 | 119.25 (17) |
O2i—Cu1—O3 | 91.95 (5) | N1—C1—C2 | 120.43 (17) |
O1—Cu1—O3 | 92.39 (6) | C6—C2—C3 | 118.76 (18) |
O1i—Cu1—O3 | 87.61 (6) | C6—C2—C1 | 115.97 (17) |
O5—Cl1—O4 | 111.2 (11) | C3—C2—C1 | 125.21 (18) |
O5—Cl1—O3 | 113.0 (8) | C4—C3—C2 | 119.64 (19) |
O4—Cl1—O3 | 107.1 (9) | C4—C3—H3 | 120.2 |
O4B—Cl1—O5B | 107.8 (10) | C2—C3—H3 | 120.2 |
O5—Cl1—O6 | 113.5 (5) | C5—C4—C3 | 119.30 (19) |
O4—Cl1—O6 | 107.5 (5) | C5—C4—H4 | 120.3 |
O3—Cl1—O6 | 104.0 (3) | C3—C4—H4 | 120.3 |
O4B—Cl1—O6B | 108.6 (5) | N2—C5—C4 | 119.48 (18) |
O5B—Cl1—O6B | 103.1 (6) | N2—C5—H5 | 120.3 |
C1—O1—Cu1 | 109.79 (12) | C4—C5—H5 | 120.3 |
N1—O2—Cu1 | 107.25 (10) | N2—C6—C2 | 119.91 (18) |
Cl1—O3—Cu1 | 120.10 (10) | N2—C6—H6 | 120.0 |
C1—N1—O2 | 117.72 (16) | C2—C6—H6 | 120.0 |
| | | |
O2—Cu1—O1—C1 | −4.25 (13) | Cu1—O1—C1—N1 | 4.3 (2) |
O2i—Cu1—O1—C1 | 175.75 (13) | Cu1—O1—C1—C2 | −176.03 (13) |
O3—Cu1—O1—C1 | −92.07 (13) | O2—N1—C1—O1 | −1.5 (3) |
O1—Cu1—O2—N1 | 3.42 (11) | O2—N1—C1—C2 | 178.89 (16) |
O1i—Cu1—O2—N1 | −176.58 (11) | O1—C1—C2—C6 | 14.5 (3) |
O3—Cu1—O2—N1 | 95.99 (11) | N1—C1—C2—C6 | −165.83 (17) |
O5—Cl1—O3—Cu1 | −165.3 (10) | O1—C1—C2—C3 | −162.50 (19) |
O4B—Cl1—O3—Cu1 | −26.0 (9) | N1—C1—C2—C3 | 17.1 (3) |
O4—Cl1—O3—Cu1 | −42.4 (8) | C6—C2—C3—C4 | 0.0 (3) |
O5B—Cl1—O3—Cu1 | −147.0 (7) | C1—C2—C3—C4 | 176.98 (19) |
O6—Cl1—O3—Cu1 | 71.2 (10) | C2—C3—C4—C5 | 0.1 (3) |
O6B—Cl1—O3—Cu1 | 100.2 (11) | C6—N2—C5—C4 | −0.7 (3) |
O2—Cu1—O3—Cl1 | 168.24 (12) | C3—C4—C5—N2 | 0.2 (3) |
O2i—Cu1—O3—Cl1 | −11.76 (12) | C5—N2—C6—C2 | 0.8 (3) |
O1—Cu1—O3—Cl1 | −107.14 (11) | C3—C2—C6—N2 | −0.5 (3) |
O1i—Cu1—O3—Cl1 | 72.86 (11) | C1—C2—C6—N2 | −177.73 (17) |
Cu1—O2—N1—C1 | −2.21 (19) | | |
Symmetry code: (i) −x+1/2, −y+3/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O6ii | 0.86 (3) | 2.02 (3) | 2.868 (6) | 169 (3) |
N1—H1N···O6Bii | 0.86 (3) | 2.04 (3) | 2.886 (7) | 170 (3) |
N2—H2N···O2iii | 0.84 (3) | 1.90 (3) | 2.704 (2) | 158 (2) |
Symmetry codes: (ii) x+1/2, y+1/2, z; (iii) x, −y+2, z+1/2. |