Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014528/tk2030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014528/tk2030Isup2.hkl |
CCDC reference: 608513
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.064
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.79
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 2107 Count of symmetry unique reflns 1139 Completeness (_total/calc) 184.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 968 Fraction of Friedel pairs measured 0.850 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 135 The title complex, [Cu(C~5~H~7~O~2~)~2~(C~7~H10~N~2~)], is disposed about a If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and WinGX32 (Farrugia, 1999); software used to prepare material for publication: enCIFer (Allen et al., 2004).
[Cu(C5H7O2)2(C7H10N2)] | F(000) = 1608 |
Mr = 383.92 | Dx = 1.458 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 6762 reflections |
a = 11.3708 (11) Å | θ = 2.7–28.3° |
b = 27.215 (3) Å | µ = 1.27 mm−1 |
c = 11.3000 (11) Å | T = 150 K |
V = 3496.9 (6) Å3 | Prism, green |
Z = 8 | 0.49 × 0.32 × 0.26 mm |
Bruker SMART 1000 CCD diffractometer | 2107 independent reflections |
Radiation source: sealed tube | 2048 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 28.3°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −14→15 |
Tmin = 0.633, Tmax = 0.718 | k = −36→36 |
8108 measured reflections | l = −15→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0425P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2107 reflections | Δρmax = 0.91 e Å−3 |
114 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 968 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.042 (11) |
Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. 163 standard reflections were obtained by recollecting the first 50 CCD frames at the end of data collection. They were then used for a decay correction, giving an overall decay of 0.20%. ESI–MS (m/z): 406 {M + Na}+, 285 {M - acac + H}+. UV–Vis (solid state): 592, 757 nm. FTIR (KBr): 583, 783, 827, 924, 1194, 1234, 1265, 1409, 1536, 1585 cm-1. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.92501 (16) | 0.36633 (6) | 1.07938 (18) | 0.0282 (4) | |
H1A | 0.9706 | 0.3856 | 1.0223 | 0.042* | |
H1B | 0.9772 | 0.3432 | 1.1201 | 0.042* | |
H1C | 0.8889 | 0.3884 | 1.1375 | 0.042* | |
C2 | 0.82995 (15) | 0.33823 (6) | 1.01499 (15) | 0.0216 (3) | |
C3 | 0.71763 (17) | 0.35940 (6) | 1.00660 (15) | 0.0226 (3) | |
H3 | 0.7049 | 0.3899 | 1.0454 | 0.027* | |
C4 | 0.62307 (13) | 0.33858 (6) | 0.94479 (14) | 0.0192 (3) | |
C5 | 0.50990 (15) | 0.36720 (8) | 0.93475 (18) | 0.0266 (4) | |
H5A | 0.4442 | 0.3467 | 0.9614 | 0.040* | |
H5B | 0.4973 | 0.3768 | 0.8521 | 0.040* | |
H5C | 0.5147 | 0.3967 | 0.9842 | 0.040* | |
C6 | 0.65032 (16) | 0.25476 (6) | 0.64031 (17) | 0.0211 (3) | |
H6 | 0.5786 | 0.2586 | 0.6825 | 0.025* | |
C7 | 0.6458 (2) | 0.25440 (6) | 0.5187 (2) | 0.0205 (4) | |
H7 | 0.5722 | 0.2571 | 0.4795 | 0.025* | |
C8 | 0.7500 | 0.2500 | 0.4522 (3) | 0.0195 (7) | |
C9 | 0.6391 (3) | 0.25096 (6) | 0.2669 (2) | 0.0254 (5) | |
H9A | 0.5992 | 0.2823 | 0.2810 | 0.038* | |
H9B | 0.5888 | 0.2239 | 0.2939 | 0.038* | |
H9C | 0.6546 | 0.2472 | 0.1820 | 0.038* | |
N1 | 0.7500 | 0.2500 | 0.7030 (2) | 0.0193 (4) | |
N2 | 0.7500 | 0.2500 | 0.3317 (3) | 0.0238 (7) | |
O1 | 0.86018 (10) | 0.29770 (4) | 0.97011 (12) | 0.0238 (3) | |
O2 | 0.62307 (9) | 0.29708 (4) | 0.89236 (13) | 0.0216 (2) | |
Cu1 | 0.7500 | 0.2500 | 0.89056 (2) | 0.01788 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0289 (9) | 0.0258 (8) | 0.0300 (9) | −0.0026 (7) | −0.0068 (7) | −0.0047 (7) |
C2 | 0.0255 (8) | 0.0195 (7) | 0.0197 (7) | −0.0029 (6) | −0.0020 (6) | 0.0009 (6) |
C3 | 0.0269 (7) | 0.0191 (8) | 0.0217 (7) | 0.0016 (7) | 0.0006 (6) | −0.0028 (6) |
C4 | 0.0221 (8) | 0.0175 (7) | 0.0179 (7) | 0.0027 (6) | 0.0023 (6) | 0.0022 (6) |
C5 | 0.0253 (9) | 0.0239 (9) | 0.0307 (9) | 0.0095 (6) | 0.0005 (6) | −0.0044 (7) |
C6 | 0.0172 (8) | 0.0243 (8) | 0.0218 (8) | 0.0019 (5) | 0.0051 (6) | −0.0016 (7) |
C7 | 0.0105 (9) | 0.0279 (9) | 0.0231 (10) | −0.0004 (6) | −0.0030 (7) | −0.0013 (7) |
C8 | 0.0226 (18) | 0.0161 (15) | 0.0198 (14) | −0.0007 (7) | 0.000 | 0.000 |
C9 | 0.0266 (12) | 0.0321 (12) | 0.0176 (10) | −0.0018 (6) | −0.0069 (9) | −0.0003 (7) |
N1 | 0.0205 (10) | 0.0159 (9) | 0.0213 (10) | 0.0008 (6) | 0.000 | 0.000 |
N2 | 0.0140 (14) | 0.0408 (19) | 0.0165 (12) | 0.0011 (7) | 0.000 | 0.000 |
O1 | 0.0203 (5) | 0.0210 (6) | 0.0301 (7) | 0.0014 (4) | −0.0044 (5) | −0.0042 (5) |
O2 | 0.0188 (5) | 0.0185 (5) | 0.0275 (6) | 0.0041 (4) | −0.0002 (5) | −0.0039 (5) |
Cu1 | 0.01620 (12) | 0.01505 (13) | 0.02238 (13) | 0.00286 (10) | 0.000 | 0.000 |
C1—C2 | 1.511 (2) | C7—C8 | 1.408 (3) |
C1—H1A | 0.9800 | C7—H7 | 0.9500 |
C1—H1B | 0.9800 | C8—N2 | 1.361 (3) |
C1—H1C | 0.9800 | C9—N2 | 1.459 (3) |
C2—O1 | 1.262 (2) | C9—H9A | 0.9800 |
C2—C3 | 1.404 (2) | C9—H9B | 0.9800 |
C3—C4 | 1.402 (2) | C9—H9C | 0.9800 |
C3—H3 | 0.9500 | N1—C6i | 1.343 (2) |
C4—O2 | 1.275 (2) | N2—C9i | 1.459 (3) |
C4—C5 | 1.508 (2) | Cu1—O1i | 2.0156 (12) |
C5—H5A | 0.9800 | Cu1—O2i | 1.9301 (10) |
C5—H5B | 0.9800 | Cu1—O1 | 2.0156 (12) |
C5—H5C | 0.9800 | Cu1—O2 | 1.9301 (10) |
C6—N1 | 1.343 (2) | Cu1—N1 | 2.119 (2) |
C6—C7 | 1.375 (3) | C8—C7i | 1.408 (3) |
C6—H6 | 0.9500 | ||
C2—C1—H1A | 109.5 | N2—C8—C7i | 122.27 (18) |
C2—C1—H1B | 109.5 | N2—C8—C7 | 122.27 (18) |
H1A—C1—H1B | 109.5 | C7i—C8—C7 | 115.5 (4) |
C2—C1—H1C | 109.5 | N2—C9—H9A | 109.5 |
H1A—C1—H1C | 109.5 | N2—C9—H9B | 109.5 |
H1B—C1—H1C | 109.5 | H9A—C9—H9B | 109.5 |
O1—C2—C3 | 125.40 (15) | N2—C9—H9C | 109.5 |
O1—C2—C1 | 116.18 (15) | H9A—C9—H9C | 109.5 |
C3—C2—C1 | 118.39 (15) | H9B—C9—H9C | 109.5 |
C4—C3—C2 | 124.43 (16) | C6—N1—C6i | 116.3 (2) |
C4—C3—H3 | 117.8 | C6—N1—Cu1 | 121.86 (11) |
C2—C3—H3 | 117.8 | C6i—N1—Cu1 | 121.86 (11) |
O2—C4—C3 | 126.12 (15) | C8—N2—C9 | 120.16 (17) |
O2—C4—C5 | 114.98 (14) | C8—N2—C9i | 120.16 (17) |
C3—C4—C5 | 118.88 (16) | C9—N2—C9i | 119.7 (3) |
C4—C5—H5A | 109.5 | C2—O1—Cu1 | 124.96 (11) |
C4—C5—H5B | 109.5 | C4—O2—Cu1 | 126.36 (10) |
H5A—C5—H5B | 109.5 | O2—Cu1—O1i | 87.60 (5) |
C4—C5—H5C | 109.5 | O2i—Cu1—O1i | 91.86 (5) |
H5A—C5—H5C | 109.5 | O1—Cu1—O1i | 127.03 (8) |
H5B—C5—H5C | 109.5 | O2i—Cu1—N1 | 90.60 (5) |
N1—C6—C7 | 123.93 (19) | O1i—Cu1—N1 | 116.48 (4) |
N1—C6—H6 | 118.0 | O1—Cu1—O2 | 91.86 (5) |
C7—C6—H6 | 118.0 | O1—Cu1—N1 | 116.48 (4) |
C6—C7—C8 | 120.2 (2) | O1i—Cu1—O2 | 87.60 (5) |
C6—C7—H7 | 119.9 | O2—Cu1—N1 | 90.60 (5) |
C8—C7—H7 | 119.9 | O2—Cu1—O2i | 178.79 (9) |
O1—C2—C3—C4 | −1.1 (3) | C5—C4—O2—Cu1 | −177.97 (13) |
C1—C2—C3—C4 | 176.81 (16) | C4—O2—Cu1—O1 | −8.17 (14) |
C2—C3—C4—O2 | 3.3 (3) | C4—O2—Cu1—O1i | 118.83 (14) |
C2—C3—C4—C5 | −175.16 (17) | C4—O2—Cu1—N1 | −124.69 (13) |
N1—C6—C7—C8 | −1.5 (3) | C2—O1—Cu1—O2 | 9.92 (15) |
C6—C7—C8—N2 | −179.28 (12) | C2—O1—Cu1—O2i | −169.00 (14) |
C6—C7—C8—C7i | 0.72 (12) | C2—O1—Cu1—O1i | −78.48 (14) |
C7—C6—N1—C6i | 0.78 (13) | C2—O1—Cu1—N1 | 101.52 (14) |
C7—C6—N1—Cu1 | −179.22 (13) | C6—N1—Cu1—O2 | −35.08 (9) |
C7i—C8—N2—C9 | 175.41 (11) | C6i—N1—Cu1—O2 | 144.92 (9) |
C7—C8—N2—C9 | −4.59 (11) | C6—N1—Cu1—O2i | 144.92 (9) |
C7i—C8—N2—C9i | −4.59 (11) | C6i—N1—Cu1—O2i | −35.08 (9) |
C7—C8—N2—C9i | 175.41 (11) | C6—N1—Cu1—O1 | −127.46 (8) |
C3—C2—O1—Cu1 | −7.0 (2) | C6i—N1—Cu1—O1 | 52.54 (8) |
C1—C2—O1—Cu1 | 174.97 (11) | C6—N1—Cu1—O1i | 52.54 (8) |
C3—C4—O2—Cu1 | 3.5 (2) | C6i—N1—Cu1—O1i | −127.46 (8) |
Symmetry code: (i) −x+3/2, −y+1/2, z. |