The title complex, [Cu(C
14H
12N
3O
2)
2], consists of two deprotonated 2-acetylpyridine salicylhydrazone ligands coordinated to the copper as
N,
N,
O-tridentate ligands, forming a neutral complex. The Cu atom lies on a twofold rotation axis. The structure is stabilized by intramolecular O—H
N hydrogen bonding, and π–π stacking interactions between the pyridyl and benzene rings lead to a two-dimensional network in the crystal structure.
Supporting information
CCDC reference: 613707
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.036
- wR factor = 0.077
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.21
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16
N2 -CU1 -N2 -C6 -131.50 0.30 2.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21
N2 -CU1 -N2 -N3 40.90 0.20 2.555 1.555 1.555 1.555
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 25.50
From the CIF: _reflns_number_total 1968
Count of symmetry unique reflns 1230
Completeness (_total/calc) 160.00%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 738
Fraction of Friedel pairs measured 0.600
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis{
N-(2-hydroxybenzoyl)-
N'-[1-(2-pyridyl)ethylidene]hydrazinato]copper(II)
top
Crystal data top
[Cu(C14H12N3O2)2] | F(000) = 1180 |
Mr = 572.07 | Dx = 1.516 Mg m−3 |
Orthorhombic, Aba2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: A 2 -2ac | Cell parameters from 1902 reflections |
a = 12.570 (2) Å | θ = 2.7–22.0° |
b = 18.731 (4) Å | µ = 0.92 mm−1 |
c = 10.6482 (19) Å | T = 293 K |
V = 2507.1 (8) Å3 | Block, green |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1628 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.5°, θmin = 2.2° |
φ and ω scans | h = −13→15 |
6226 measured reflections | k = −22→22 |
1968 independent reflections | l = −10→12 |
Refinement top
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1968 reflections | Δρmax = 0.52 e Å−3 |
179 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.018 (19) |
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 | |
Cu1 | 0.0000 | 0.0000 | 0.15509 (8) | 0.05477 (18) | |
O1 | −0.01374 (17) | 0.08533 (14) | 0.0199 (3) | 0.0647 (7) | |
O2 | 0.2825 (2) | 0.16322 (19) | −0.0921 (3) | 0.0944 (11) | |
H2 | 0.2684 | 0.1366 | −0.0332 | 0.142* | |
N1 | 0.0829 (2) | −0.05852 (16) | 0.2994 (3) | 0.0559 (7) | |
N2 | 0.1460 (2) | 0.03693 (15) | 0.1424 (4) | 0.0536 (7) | |
N3 | 0.1671 (2) | 0.08738 (15) | 0.0528 (3) | 0.0578 (8) | |
C1 | 0.0453 (4) | −0.1023 (2) | 0.3847 (5) | 0.0796 (12) | |
H1 | −0.0266 | −0.1138 | 0.3824 | 0.096* | |
C2 | 0.1079 (5) | −0.1322 (2) | 0.4778 (5) | 0.1006 (17) | |
H2A | 0.0786 | −0.1619 | 0.5386 | 0.121* | |
C3 | 0.2147 (5) | −0.1166 (3) | 0.4774 (5) | 0.1028 (18) | |
H3 | 0.2593 | −0.1370 | 0.5371 | 0.123* | |
C4 | 0.2557 (4) | −0.0708 (2) | 0.3891 (5) | 0.0782 (13) | |
H4 | 0.3277 | −0.0594 | 0.3885 | 0.094* | |
C5 | 0.1877 (3) | −0.0426 (2) | 0.3020 (3) | 0.0565 (9) | |
C6 | 0.2216 (3) | 0.00967 (18) | 0.2055 (4) | 0.0575 (10) | |
C7 | 0.3361 (3) | 0.0287 (2) | 0.1857 (5) | 0.0852 (15) | |
H7A | 0.3666 | −0.0029 | 0.1244 | 0.128* | |
H7B | 0.3740 | 0.0240 | 0.2636 | 0.128* | |
H7C | 0.3412 | 0.0770 | 0.1565 | 0.128* | |
C8 | 0.0776 (3) | 0.10946 (18) | −0.0042 (3) | 0.0534 (9) | |
C9 | 0.0921 (3) | 0.16456 (17) | −0.1038 (3) | 0.0537 (9) | |
C10 | 0.0033 (3) | 0.1935 (2) | −0.1616 (4) | 0.0657 (10) | |
H10 | −0.0639 | 0.1803 | −0.1335 | 0.079* | |
C11 | 0.0114 (3) | 0.2405 (2) | −0.2577 (4) | 0.0781 (12) | |
H11 | −0.0496 | 0.2596 | −0.2941 | 0.094* | |
C12 | 0.1099 (3) | 0.2599 (2) | −0.3009 (4) | 0.0823 (13) | |
H12 | 0.1159 | 0.2912 | −0.3683 | 0.099* | |
C13 | 0.1991 (3) | 0.2334 (2) | −0.2454 (5) | 0.0803 (13) | |
H13 | 0.2657 | 0.2467 | −0.2754 | 0.096* | |
C14 | 0.1916 (3) | 0.1868 (2) | −0.1446 (4) | 0.0687 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0486 (3) | 0.0660 (3) | 0.0497 (3) | 0.0084 (3) | 0.000 | 0.000 |
O1 | 0.0515 (15) | 0.0773 (18) | 0.0651 (18) | −0.0171 (11) | 0.0059 (12) | 0.0092 (15) |
O2 | 0.0515 (18) | 0.113 (3) | 0.119 (3) | −0.0051 (14) | 0.0164 (19) | 0.033 (2) |
N1 | 0.0522 (18) | 0.0604 (18) | 0.055 (2) | 0.0076 (14) | −0.0031 (14) | −0.0059 (16) |
N2 | 0.0467 (15) | 0.0590 (15) | 0.0552 (19) | 0.0014 (12) | −0.0021 (16) | −0.0092 (19) |
N3 | 0.0551 (18) | 0.0591 (18) | 0.059 (2) | −0.0060 (13) | 0.0037 (15) | −0.0004 (16) |
C1 | 0.087 (3) | 0.074 (3) | 0.078 (3) | 0.001 (2) | 0.016 (3) | −0.010 (3) |
C2 | 0.148 (5) | 0.083 (3) | 0.070 (4) | 0.028 (3) | 0.005 (4) | 0.013 (3) |
C3 | 0.142 (5) | 0.091 (4) | 0.075 (4) | 0.055 (3) | −0.036 (3) | −0.010 (3) |
C4 | 0.080 (3) | 0.078 (3) | 0.076 (3) | 0.026 (3) | −0.030 (3) | −0.021 (3) |
C5 | 0.053 (2) | 0.061 (2) | 0.056 (2) | 0.0171 (17) | −0.0125 (18) | −0.017 (2) |
C6 | 0.0448 (19) | 0.061 (2) | 0.067 (3) | 0.0001 (16) | −0.0022 (16) | −0.0221 (19) |
C7 | 0.050 (2) | 0.095 (3) | 0.111 (5) | −0.0083 (18) | −0.005 (2) | −0.028 (3) |
C8 | 0.056 (2) | 0.054 (2) | 0.050 (2) | −0.0076 (18) | 0.0088 (18) | −0.0109 (18) |
C9 | 0.051 (2) | 0.055 (2) | 0.055 (3) | −0.0110 (15) | 0.0062 (18) | −0.0050 (19) |
C10 | 0.054 (2) | 0.073 (2) | 0.070 (3) | −0.0091 (19) | 0.0036 (19) | 0.010 (2) |
C11 | 0.071 (3) | 0.081 (3) | 0.082 (3) | −0.010 (2) | −0.002 (2) | 0.013 (3) |
C12 | 0.085 (3) | 0.085 (3) | 0.077 (4) | −0.016 (2) | 0.010 (2) | 0.014 (2) |
C13 | 0.065 (3) | 0.087 (3) | 0.090 (3) | −0.011 (2) | 0.029 (2) | 0.017 (3) |
C14 | 0.054 (2) | 0.079 (3) | 0.073 (3) | −0.002 (2) | 0.008 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
Cu1—N2 | 1.966 (3) | C3—H3 | 0.9300 |
Cu1—N2i | 1.966 (3) | C4—C5 | 1.368 (5) |
Cu1—N1i | 2.156 (3) | C4—H4 | 0.9300 |
Cu1—N1 | 2.156 (3) | C5—C6 | 1.482 (5) |
Cu1—O1i | 2.158 (3) | C6—C7 | 1.498 (5) |
Cu1—O1 | 2.158 (3) | C7—H7A | 0.9600 |
O1—C8 | 1.260 (4) | C7—H7B | 0.9600 |
O2—C14 | 1.346 (4) | C7—H7C | 0.9600 |
O2—H2 | 0.8200 | C8—C9 | 1.491 (5) |
N1—C1 | 1.311 (5) | C9—C10 | 1.386 (5) |
N1—C5 | 1.351 (4) | C9—C14 | 1.388 (5) |
N2—C6 | 1.272 (4) | C10—C11 | 1.354 (6) |
N2—N3 | 1.369 (4) | C10—H10 | 0.9300 |
N3—C8 | 1.344 (4) | C11—C12 | 1.371 (5) |
C1—C2 | 1.384 (6) | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | C12—C13 | 1.361 (6) |
C2—C3 | 1.375 (7) | C12—H12 | 0.9300 |
C2—H2A | 0.9300 | C13—C14 | 1.387 (6) |
C3—C4 | 1.372 (7) | C13—H13 | 0.9300 |
| | | |
N2—Cu1—N2i | 172.1 (2) | C3—C4—H4 | 120.9 |
N2—Cu1—N1i | 108.75 (13) | N1—C5—C4 | 122.5 (4) |
N2i—Cu1—N1i | 77.11 (13) | N1—C5—C6 | 114.4 (3) |
N2—Cu1—N1 | 77.11 (13) | C4—C5—C6 | 123.1 (4) |
N2i—Cu1—N1 | 108.75 (13) | N2—C6—C5 | 114.6 (3) |
N1i—Cu1—N1 | 89.07 (16) | N2—C6—C7 | 123.3 (4) |
N2—Cu1—O1i | 98.04 (11) | C5—C6—C7 | 122.1 (4) |
N2i—Cu1—O1i | 76.59 (12) | C6—C7—H7A | 109.5 |
N1i—Cu1—O1i | 152.95 (10) | C6—C7—H7B | 109.5 |
N1—Cu1—O1i | 93.46 (10) | H7A—C7—H7B | 109.5 |
N2—Cu1—O1 | 76.59 (12) | C6—C7—H7C | 109.5 |
N2i—Cu1—O1 | 98.04 (11) | H7A—C7—H7C | 109.5 |
N1i—Cu1—O1 | 93.46 (11) | H7B—C7—H7C | 109.5 |
N1—Cu1—O1 | 152.95 (10) | O1—C8—N3 | 124.1 (3) |
O1i—Cu1—O1 | 96.32 (15) | O1—C8—C9 | 120.3 (3) |
C8—O1—Cu1 | 109.2 (2) | N3—C8—C9 | 115.6 (3) |
C14—O2—H2 | 109.5 | C10—C9—C14 | 118.0 (4) |
C1—N1—C5 | 118.4 (4) | C10—C9—C8 | 119.2 (3) |
C1—N1—Cu1 | 129.6 (3) | C14—C9—C8 | 122.7 (3) |
C5—N1—Cu1 | 111.9 (2) | C11—C10—C9 | 122.0 (4) |
C6—N2—N3 | 120.0 (3) | C11—C10—H10 | 119.0 |
C6—N2—Cu1 | 121.3 (3) | C9—C10—H10 | 119.0 |
N3—N2—Cu1 | 118.2 (2) | C10—C11—C12 | 119.6 (4) |
C8—N3—N2 | 111.4 (3) | C10—C11—H11 | 120.2 |
N1—C1—C2 | 123.0 (5) | C12—C11—H11 | 120.2 |
N1—C1—H1 | 118.5 | C13—C12—C11 | 120.1 (4) |
C2—C1—H1 | 118.5 | C13—C12—H12 | 119.9 |
C3—C2—C1 | 117.8 (5) | C11—C12—H12 | 119.9 |
C3—C2—H2A | 121.1 | C12—C13—C14 | 120.7 (4) |
C1—C2—H2A | 121.1 | C12—C13—H13 | 119.7 |
C4—C3—C2 | 120.1 (4) | C14—C13—H13 | 119.7 |
C4—C3—H3 | 119.9 | O2—C14—C13 | 118.1 (4) |
C2—C3—H3 | 119.9 | O2—C14—C9 | 122.5 (4) |
C5—C4—C3 | 118.1 (5) | C13—C14—C9 | 119.5 (4) |
C5—C4—H4 | 120.9 | | |
| | | |
N2—Cu1—O1—C8 | 5.5 (2) | Cu1—N1—C5—C4 | 177.2 (3) |
N2i—Cu1—O1—C8 | −168.6 (2) | C1—N1—C5—C6 | −177.5 (3) |
N1i—Cu1—O1—C8 | 114.0 (2) | Cu1—N1—C5—C6 | −0.9 (3) |
N1—Cu1—O1—C8 | 19.3 (4) | C3—C4—C5—N1 | −0.6 (6) |
O1i—Cu1—O1—C8 | −91.3 (2) | C3—C4—C5—C6 | 177.3 (4) |
N2—Cu1—N1—C1 | 173.4 (4) | N3—N2—C6—C5 | 178.2 (3) |
N2i—Cu1—N1—C1 | −12.1 (4) | Cu1—N2—C6—C5 | −9.4 (4) |
N1i—Cu1—N1—C1 | 63.9 (3) | N3—N2—C6—C7 | −1.4 (5) |
O1i—Cu1—N1—C1 | −89.2 (3) | Cu1—N2—C6—C7 | 170.9 (3) |
O1—Cu1—N1—C1 | 159.7 (3) | N1—C5—C6—N2 | 6.3 (4) |
N2—Cu1—N1—C5 | −2.7 (2) | C4—C5—C6—N2 | −171.7 (3) |
N2i—Cu1—N1—C5 | 171.7 (2) | N1—C5—C6—C7 | −174.1 (3) |
N1i—Cu1—N1—C5 | −112.2 (3) | C4—C5—C6—C7 | 7.9 (5) |
O1i—Cu1—N1—C5 | 94.7 (2) | Cu1—O1—C8—N3 | −3.8 (4) |
O1—Cu1—N1—C5 | −16.4 (4) | Cu1—O1—C8—C9 | 174.4 (2) |
N2i—Cu1—N2—C6 | −131.5 (3) | N2—N3—C8—O1 | −1.6 (4) |
N1i—Cu1—N2—C6 | 91.5 (3) | N2—N3—C8—C9 | −179.9 (3) |
N1—Cu1—N2—C6 | 7.0 (3) | O1—C8—C9—C10 | 5.8 (5) |
O1i—Cu1—N2—C6 | −84.8 (3) | N3—C8—C9—C10 | −175.9 (3) |
O1—Cu1—N2—C6 | −179.4 (3) | O1—C8—C9—C14 | −172.1 (3) |
N2i—Cu1—N2—N3 | 40.9 (2) | N3—C8—C9—C14 | 6.2 (5) |
N1i—Cu1—N2—N3 | −96.0 (2) | C14—C9—C10—C11 | 2.0 (6) |
N1—Cu1—N2—N3 | 179.4 (3) | C8—C9—C10—C11 | −176.0 (4) |
O1i—Cu1—N2—N3 | 87.7 (2) | C9—C10—C11—C12 | 0.7 (7) |
O1—Cu1—N2—N3 | −6.9 (2) | C10—C11—C12—C13 | −1.6 (7) |
C6—N2—N3—C8 | 179.7 (3) | C11—C12—C13—C14 | −0.2 (7) |
Cu1—N2—N3—C8 | 7.1 (3) | C12—C13—C14—O2 | −178.9 (4) |
C5—N1—C1—C2 | 0.8 (6) | C12—C13—C14—C9 | 2.9 (6) |
Cu1—N1—C1—C2 | −175.1 (3) | C10—C9—C14—O2 | 178.1 (4) |
N1—C1—C2—C3 | −2.1 (7) | C8—C9—C14—O2 | −4.0 (6) |
C1—C2—C3—C4 | 2.0 (7) | C10—C9—C14—C13 | −3.8 (6) |
C2—C3—C4—C5 | −0.8 (7) | C8—C9—C14—C13 | 174.1 (4) |
C1—N1—C5—C4 | 0.6 (5) | | |
Symmetry code: (i) −x, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3 | 0.82 | 1.82 | 2.550 (4) | 148 |