(3,5-Dimethyl-1H-pyrazole-κN2)(4-oxidopent-3-en-2-one 2-hydroxybenzoylhydrazonato-κ2N,O)copper(II)
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000372/wk2036sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000372/wk2036Isup2.hkl |
CCDC reference: 636823
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.091
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.538 0.774 Tmin(prime) and Tmax expected: 0.441 0.561 RR(prime) = 0.884 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.73 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O3 -CU1 -O2 -C7 39.10 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 5 O2 -CU1 -O3 -C11 -32.30 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N3 -CU1 -N2 -C9 -114.00 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N3 -CU1 -N2 -N1 66.50 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N2 -CU1 -N3 -C14 -57.70 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 N2 -CU1 -N3 -N4 119.60 0.60 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
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 0.725 Tmax scaled 0.561 Tmin scaled 0.390 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 3 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 4 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97/2.
[Cu(C12H12N2O3)(C5H8N2)] | Z = 2 |
Mr = 391.91 | F(000) = 406 |
Triclinic, P1 | Dx = 1.501 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0713 (7) Å | Cell parameters from 3907 reflections |
b = 10.6660 (11) Å | θ = 2.6–27.5° |
c = 10.9429 (8) Å | µ = 1.28 mm−1 |
α = 110.393 (4)° | T = 293 K |
β = 96.174 (3)° | Block, black |
γ = 96.299 (4)° | 0.62 × 0.53 × 0.45 mm |
V = 866.87 (13) Å3 |
Rigaku Weissenberg IP area-detector diffractometer | 3907 independent reflections |
Radiation source: fine-focus sealed tube | 3549 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: ψ scan (TEXRAY; Molecular Structure Corporation, 1999) | h = −10→10 |
Tmin = 0.538, Tmax = 0.774 | k = 0→13 |
8035 measured reflections | l = −14→13 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.356P] where P = (Fo2 + 2Fc2)/3 |
3907 reflections | (Δ/σ)max < 0.001 |
232 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
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 | ||
Cu1 | 0.32166 (3) | 0.04733 (2) | 0.43229 (2) | 0.03629 (9) | |
O1 | 0.7545 (3) | 0.50508 (19) | 0.60846 (19) | 0.0663 (5) | |
H01 | 0.6879 | 0.4312 | 0.5424 | 0.073 (9)* | |
O2 | 0.44823 (19) | 0.15762 (15) | 0.60425 (14) | 0.0461 (3) | |
O3 | 0.21695 (19) | −0.05728 (15) | 0.25458 (14) | 0.0432 (3) | |
N1 | 0.5481 (2) | 0.28407 (17) | 0.48744 (17) | 0.0391 (4) | |
N2 | 0.4483 (2) | 0.17950 (17) | 0.38205 (17) | 0.0380 (3) | |
N3 | 0.1760 (2) | −0.07361 (16) | 0.49460 (16) | 0.0363 (3) | |
N4 | 0.0805 (2) | −0.18331 (17) | 0.39976 (17) | 0.0394 (4) | |
H4B | 0.0826 | −0.2036 | 0.3167 | 0.047* | |
C1 | 0.6301 (2) | 0.3684 (2) | 0.7213 (2) | 0.0399 (4) | |
C2 | 0.7339 (3) | 0.4830 (2) | 0.7206 (2) | 0.0480 (5) | |
C3 | 0.8180 (4) | 0.5793 (3) | 0.8393 (3) | 0.0648 (7) | |
H3A | 0.8868 | 0.6549 | 0.8389 | 0.078* | |
C4 | 0.8011 (4) | 0.5645 (3) | 0.9570 (3) | 0.0665 (7) | |
H4A | 0.8585 | 0.6299 | 1.0355 | 0.080* | |
C5 | 0.6990 (4) | 0.4529 (3) | 0.9598 (3) | 0.0635 (7) | |
H5A | 0.6870 | 0.4433 | 1.0398 | 0.076* | |
C6 | 0.6154 (3) | 0.3561 (2) | 0.8430 (2) | 0.0516 (5) | |
H6A | 0.5475 | 0.2808 | 0.8451 | 0.062* | |
C7 | 0.5368 (2) | 0.2640 (2) | 0.5988 (2) | 0.0379 (4) | |
C8 | 0.5657 (3) | 0.2929 (3) | 0.2440 (3) | 0.0570 (6) | |
H8A | 0.5385 | 0.3792 | 0.2953 | 0.085* | |
H8B | 0.5499 | 0.2816 | 0.1523 | 0.085* | |
H8C | 0.6811 | 0.2888 | 0.2720 | 0.085* | |
C9 | 0.4522 (3) | 0.1821 (2) | 0.2633 (2) | 0.0414 (4) | |
C10 | 0.3518 (3) | 0.0794 (2) | 0.1511 (2) | 0.0465 (5) | |
H10A | 0.3589 | 0.0833 | 0.0652 | 0.061 (8)* | |
C11 | 0.2441 (3) | −0.0300 (2) | 0.15091 (19) | 0.0414 (4) | |
C12 | 0.1443 (3) | −0.1298 (3) | 0.0236 (2) | 0.0548 (6) | |
H12A | 0.1642 | −0.2196 | 0.0141 | 0.082* | |
H12B | 0.1786 | −0.1083 | −0.0490 | 0.082* | |
H12C | 0.0263 | −0.1252 | 0.0245 | 0.082* | |
C13 | 0.2148 (3) | 0.0264 (3) | 0.7394 (2) | 0.0508 (5) | |
H13A | 0.2377 | 0.1128 | 0.7305 | 0.076* | |
H13B | 0.3183 | 0.0022 | 0.7697 | 0.076* | |
H13C | 0.1386 | 0.0315 | 0.8019 | 0.076* | |
C14 | 0.1368 (2) | −0.0781 (2) | 0.6090 (2) | 0.0398 (4) | |
C15 | 0.0153 (3) | −0.1918 (2) | 0.5839 (2) | 0.0473 (5) | |
H15A | −0.0335 | −0.2182 | 0.6461 | 0.057* | |
C16 | −0.0177 (3) | −0.2569 (2) | 0.4492 (2) | 0.0441 (5) | |
C17 | −0.1356 (3) | −0.3825 (3) | 0.3632 (3) | 0.0601 (6) | |
H17A | −0.2145 | −0.3608 | 0.3043 | 0.090* | |
H17B | −0.1957 | −0.4195 | 0.4171 | 0.090* | |
H17C | −0.0723 | −0.4478 | 0.3128 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03704 (14) | 0.03588 (14) | 0.03216 (14) | −0.00648 (9) | 0.00272 (9) | 0.01216 (10) |
O1 | 0.0786 (12) | 0.0535 (10) | 0.0545 (10) | −0.0258 (9) | −0.0010 (9) | 0.0188 (8) |
O2 | 0.0508 (8) | 0.0449 (8) | 0.0357 (7) | −0.0143 (6) | 0.0010 (6) | 0.0142 (6) |
O3 | 0.0488 (8) | 0.0420 (8) | 0.0333 (7) | −0.0085 (6) | 0.0034 (6) | 0.0124 (6) |
N1 | 0.0374 (8) | 0.0365 (8) | 0.0396 (9) | −0.0034 (6) | 0.0029 (7) | 0.0126 (7) |
N2 | 0.0368 (8) | 0.0374 (8) | 0.0359 (8) | −0.0047 (6) | 0.0028 (7) | 0.0126 (7) |
N3 | 0.0349 (8) | 0.0361 (8) | 0.0362 (8) | −0.0014 (6) | 0.0048 (6) | 0.0133 (7) |
N4 | 0.0395 (8) | 0.0362 (8) | 0.0388 (9) | −0.0034 (7) | 0.0046 (7) | 0.0124 (7) |
C1 | 0.0375 (9) | 0.0352 (9) | 0.0411 (10) | 0.0012 (7) | 0.0035 (8) | 0.0088 (8) |
C2 | 0.0485 (11) | 0.0400 (11) | 0.0467 (12) | −0.0052 (9) | 0.0018 (9) | 0.0102 (9) |
C3 | 0.0721 (16) | 0.0455 (13) | 0.0580 (15) | −0.0193 (12) | −0.0039 (13) | 0.0082 (11) |
C4 | 0.0748 (17) | 0.0516 (14) | 0.0494 (13) | −0.0117 (12) | −0.0076 (12) | 0.0007 (11) |
C5 | 0.0756 (17) | 0.0604 (15) | 0.0415 (12) | −0.0056 (13) | 0.0021 (12) | 0.0096 (11) |
C6 | 0.0574 (13) | 0.0478 (12) | 0.0406 (11) | −0.0059 (10) | 0.0049 (10) | 0.0100 (10) |
C7 | 0.0348 (9) | 0.0355 (9) | 0.0390 (10) | −0.0004 (7) | 0.0037 (8) | 0.0106 (8) |
C8 | 0.0603 (14) | 0.0575 (14) | 0.0555 (14) | −0.0116 (11) | 0.0073 (11) | 0.0302 (12) |
C9 | 0.0416 (10) | 0.0429 (10) | 0.0417 (10) | −0.0004 (8) | 0.0074 (8) | 0.0196 (9) |
C10 | 0.0526 (12) | 0.0517 (12) | 0.0346 (10) | −0.0035 (9) | 0.0039 (9) | 0.0193 (9) |
C11 | 0.0450 (10) | 0.0434 (10) | 0.0320 (9) | 0.0012 (8) | 0.0045 (8) | 0.0113 (8) |
C12 | 0.0674 (15) | 0.0524 (13) | 0.0354 (10) | −0.0068 (11) | 0.0000 (10) | 0.0118 (10) |
C13 | 0.0536 (12) | 0.0603 (14) | 0.0386 (11) | 0.0010 (10) | 0.0095 (9) | 0.0197 (10) |
C14 | 0.0381 (9) | 0.0451 (11) | 0.0412 (10) | 0.0058 (8) | 0.0085 (8) | 0.0214 (9) |
C15 | 0.0460 (11) | 0.0496 (12) | 0.0528 (12) | 0.0004 (9) | 0.0120 (10) | 0.0275 (10) |
C16 | 0.0387 (10) | 0.0405 (10) | 0.0552 (12) | −0.0019 (8) | 0.0082 (9) | 0.0223 (10) |
C17 | 0.0541 (13) | 0.0461 (13) | 0.0715 (17) | −0.0132 (10) | 0.0050 (12) | 0.0186 (12) |
Cu1—O3 | 1.9153 (14) | C5—H5A | 0.9300 |
Cu1—N2 | 1.9180 (16) | C6—H6A | 0.9300 |
Cu1—O2 | 1.9361 (14) | C8—C9 | 1.503 (3) |
Cu1—N3 | 1.9911 (16) | C8—H8A | 0.9600 |
O1—C2 | 1.351 (3) | C8—H8B | 0.9600 |
O1—H01 | 0.9266 | C8—H8C | 0.9600 |
O2—C7 | 1.296 (2) | C9—C10 | 1.421 (3) |
O3—C11 | 1.300 (2) | C10—C11 | 1.375 (3) |
N1—C7 | 1.319 (3) | C10—H10A | 0.9630 |
N1—N2 | 1.389 (2) | C11—C12 | 1.503 (3) |
N2—C9 | 1.313 (3) | C12—H12A | 0.9600 |
N3—C14 | 1.340 (3) | C12—H12B | 0.9600 |
N3—N4 | 1.351 (2) | C12—H12C | 0.9600 |
N4—C16 | 1.338 (3) | C13—C14 | 1.489 (3) |
N4—H4B | 0.8600 | C13—H13A | 0.9600 |
C1—C6 | 1.399 (3) | C13—H13B | 0.9600 |
C1—C2 | 1.407 (3) | C13—H13C | 0.9600 |
C1—C7 | 1.471 (3) | C14—C15 | 1.399 (3) |
C2—C3 | 1.389 (3) | C15—C16 | 1.374 (3) |
C3—C4 | 1.370 (4) | C15—H15A | 0.9300 |
C3—H3A | 0.9300 | C16—C17 | 1.495 (3) |
C4—C5 | 1.382 (4) | C17—H17A | 0.9600 |
C4—H4A | 0.9300 | C17—H17B | 0.9600 |
C5—C6 | 1.377 (3) | C17—H17C | 0.9600 |
O3—Cu1—N2 | 93.22 (6) | C9—C8—H8B | 109.5 |
O3—Cu1—O2 | 173.97 (6) | H8A—C8—H8B | 109.5 |
N2—Cu1—O2 | 81.76 (6) | C9—C8—H8C | 109.5 |
O3—Cu1—N3 | 89.24 (6) | H8A—C8—H8C | 109.5 |
N2—Cu1—N3 | 173.60 (7) | H8B—C8—H8C | 109.5 |
O2—Cu1—N3 | 96.10 (6) | N2—C9—C10 | 120.72 (18) |
C2—O1—H01 | 104.1 | N2—C9—C8 | 120.28 (19) |
C7—O2—Cu1 | 110.40 (13) | C10—C9—C8 | 118.99 (19) |
C11—O3—Cu1 | 125.59 (13) | C11—C10—C9 | 126.46 (19) |
C7—N1—N2 | 110.46 (16) | C11—C10—H10A | 114.8 |
C9—N2—N1 | 117.64 (16) | C9—C10—H10A | 118.7 |
C9—N2—Cu1 | 128.44 (14) | O3—C11—C10 | 125.54 (19) |
N1—N2—Cu1 | 113.91 (12) | O3—C11—C12 | 114.17 (18) |
C14—N3—N4 | 105.48 (16) | C10—C11—C12 | 120.29 (19) |
C14—N3—Cu1 | 138.34 (14) | C11—C12—H12A | 109.5 |
N4—N3—Cu1 | 116.14 (13) | C11—C12—H12B | 109.5 |
C16—N4—N3 | 112.56 (17) | H12A—C12—H12B | 109.5 |
C16—N4—H4B | 123.7 | C11—C12—H12C | 109.5 |
N3—N4—H4B | 123.7 | H12A—C12—H12C | 109.5 |
C6—C1—C2 | 118.2 (2) | H12B—C12—H12C | 109.5 |
C6—C1—C7 | 119.98 (19) | C14—C13—H13A | 109.5 |
C2—C1—C7 | 121.83 (19) | C14—C13—H13B | 109.5 |
O1—C2—C3 | 117.9 (2) | H13A—C13—H13B | 109.5 |
O1—C2—C1 | 122.7 (2) | C14—C13—H13C | 109.5 |
C3—C2—C1 | 119.4 (2) | H13A—C13—H13C | 109.5 |
C4—C3—C2 | 121.1 (2) | H13B—C13—H13C | 109.5 |
C4—C3—H3A | 119.5 | N3—C14—C15 | 109.45 (19) |
C2—C3—H3A | 119.5 | N3—C14—C13 | 122.68 (18) |
C3—C4—C5 | 120.4 (2) | C15—C14—C13 | 127.88 (19) |
C3—C4—H4A | 119.8 | C16—C15—C14 | 106.51 (19) |
C5—C4—H4A | 119.8 | C16—C15—H15A | 126.7 |
C6—C5—C4 | 119.4 (3) | C14—C15—H15A | 126.7 |
C6—C5—H5A | 120.3 | N4—C16—C15 | 106.01 (18) |
C4—C5—H5A | 120.3 | N4—C16—C17 | 122.3 (2) |
C5—C6—C1 | 121.6 (2) | C15—C16—C17 | 131.7 (2) |
C5—C6—H6A | 119.2 | C16—C17—H17A | 109.5 |
C1—C6—H6A | 119.2 | C16—C17—H17B | 109.5 |
O2—C7—N1 | 123.12 (18) | H17A—C17—H17B | 109.5 |
O2—C7—C1 | 119.40 (18) | C16—C17—H17C | 109.5 |
N1—C7—C1 | 117.48 (17) | H17A—C17—H17C | 109.5 |
C9—C8—H8A | 109.5 | H17B—C17—H17C | 109.5 |
O3—Cu1—O2—C7 | 39.1 (7) | C2—C1—C6—C5 | 0.2 (4) |
N2—Cu1—O2—C7 | 5.28 (14) | C7—C1—C6—C5 | −179.1 (2) |
N3—Cu1—O2—C7 | −168.64 (14) | Cu1—O2—C7—N1 | −5.9 (3) |
N2—Cu1—O3—C11 | 1.10 (18) | Cu1—O2—C7—C1 | 174.18 (14) |
O2—Cu1—O3—C11 | −32.3 (7) | N2—N1—C7—O2 | 2.3 (3) |
N3—Cu1—O3—C11 | 175.19 (18) | N2—N1—C7—C1 | −177.73 (16) |
C7—N1—N2—C9 | −177.03 (19) | C6—C1—C7—O2 | −3.5 (3) |
C7—N1—N2—Cu1 | 2.6 (2) | C2—C1—C7—O2 | 177.2 (2) |
O3—Cu1—N2—C9 | −1.5 (2) | C6—C1—C7—N1 | 176.5 (2) |
O2—Cu1—N2—C9 | 175.2 (2) | C2—C1—C7—N1 | −2.7 (3) |
N3—Cu1—N2—C9 | −114.0 (6) | N1—N2—C9—C10 | −179.21 (18) |
O3—Cu1—N2—N1 | 178.97 (13) | Cu1—N2—C9—C10 | 1.3 (3) |
O2—Cu1—N2—N1 | −4.38 (13) | N1—N2—C9—C8 | 1.8 (3) |
N3—Cu1—N2—N1 | 66.5 (6) | Cu1—N2—C9—C8 | −177.72 (17) |
O3—Cu1—N3—C14 | −170.4 (2) | N2—C9—C10—C11 | −0.2 (4) |
N2—Cu1—N3—C14 | −57.7 (7) | C8—C9—C10—C11 | 178.8 (2) |
O2—Cu1—N3—C14 | 12.4 (2) | Cu1—O3—C11—C10 | −0.6 (3) |
O3—Cu1—N3—N4 | 6.86 (14) | Cu1—O3—C11—C12 | 179.99 (15) |
N2—Cu1—N3—N4 | 119.6 (6) | C9—C10—C11—O3 | −0.1 (4) |
O2—Cu1—N3—N4 | −170.34 (13) | C9—C10—C11—C12 | 179.3 (2) |
C14—N3—N4—C16 | 0.2 (2) | N4—N3—C14—C15 | −0.2 (2) |
Cu1—N3—N4—C16 | −177.94 (14) | Cu1—N3—C14—C15 | 177.20 (16) |
C6—C1—C2—O1 | −179.0 (2) | N4—N3—C14—C13 | −179.68 (19) |
C7—C1—C2—O1 | 0.2 (3) | Cu1—N3—C14—C13 | −2.3 (3) |
C6—C1—C2—C3 | 0.1 (4) | N3—C14—C15—C16 | 0.2 (3) |
C7—C1—C2—C3 | 179.4 (2) | C13—C14—C15—C16 | 179.6 (2) |
O1—C2—C3—C4 | 179.0 (3) | N3—N4—C16—C15 | 0.0 (2) |
C1—C2—C3—C4 | −0.2 (4) | N3—N4—C16—C17 | 179.5 (2) |
C2—C3—C4—C5 | −0.1 (5) | C14—C15—C16—N4 | −0.1 (2) |
C3—C4—C5—C6 | 0.5 (5) | C14—C15—C16—C17 | −179.6 (2) |
C4—C5—C6—C1 | −0.5 (4) |