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In the title compound, [Cu(C9H10N4S)(C2H3O2)]·H2O, the Cu atom adopts a slightly distorted square-planar coordination geometry. The 2-acetylpyridine thiosemicarbazone group is very close to planar. The computed bond valencies for the Cu centre are ν(Cu—N) = 0.349 and 0.404 valence units (v.u.), ν(Cu—S) = 0.627 v.u., and ν(Cu—O) = 0.483 v.u. There is an out of plane Cu—O(acetate) bond [2.639 (13) Å], which makes a contribution of 0.08 v.u. The computed valency of the Cu atom is thus 1.94 v.u. Hydrogen bonds between pairs of molecules create dimers.
Supporting information
CCDC reference: 298368
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.040
- wR factor = 0.102
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT731_ALERT_1_B Bond Calc 2.640(2), Rep 2.639(13) ...... 6.50 su-Rat
CU1 -O2 1.555 1.555
Alert level C
CHEMW01_ALERT_1_C The difference between the given and expected weight for
compound is greater 1 mass unit. Check that all hydrogen
atoms have been taken into account.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O3 - H3B ... 0.63 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
(Acetato-
κO)[2-acetylpyridine
4-methylthiosemicarbazonato-
κ3N,
N',
S]copper(II)
monohydrate
top
Crystal data top
[Cu(C9H10N4S)(C2H3O2)]·H2O | F(000) = 712 |
Mr = 347.88 | Dx = 1.555 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2923 reflections |
a = 7.0091 (18) Å | θ = 0–26° |
b = 11.116 (3) Å | µ = 1.62 mm−1 |
c = 19.336 (5) Å | T = 293 K |
β = 99.442 (4)° | Rectangular block, brown |
V = 1486.1 (7) Å3 | 0.30 × 0.12 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 2906 independent reflections |
Radiation source: fine-focus sealed tube | 2299 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
φ and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −8→8 |
Tmin = 0.792, Tmax = 0.893 | k = −13→10 |
7772 measured reflections | l = −23→23 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0519P)2] where P = (Fo2 + 2Fc2)/3 |
2906 reflections | (Δ/σ)max < 0.001 |
192 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.46 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 | |
C1 | 0.2981 (5) | 0.7451 (3) | 0.56930 (17) | 0.0485 (8) | |
H1 | 0.3218 | 0.6685 | 0.5534 | 0.058* | |
C2 | 0.2751 (6) | 0.7594 (3) | 0.63764 (18) | 0.0593 (10) | |
H2 | 0.2823 | 0.6936 | 0.6676 | 0.071* | |
C3 | 0.2415 (6) | 0.8710 (4) | 0.66103 (18) | 0.0627 (10) | |
H3 | 0.2249 | 0.8821 | 0.7073 | 0.075* | |
C4 | 0.2319 (5) | 0.9680 (3) | 0.61633 (16) | 0.0494 (8) | |
H4 | 0.2101 | 1.0451 | 0.6320 | 0.059* | |
C5 | 0.2552 (4) | 0.9484 (3) | 0.54774 (15) | 0.0375 (7) | |
C6 | 0.2465 (4) | 1.0431 (3) | 0.49455 (15) | 0.0360 (7) | |
C7 | 0.2230 (5) | 1.1718 (3) | 0.51076 (19) | 0.0509 (8) | |
H7A | 0.2586 | 1.2202 | 0.4738 | 0.076* | |
H7B | 0.3046 | 1.1914 | 0.5542 | 0.076* | |
H7C | 0.0905 | 1.1872 | 0.5148 | 0.076* | |
C8 | 0.2739 (5) | 1.0304 (3) | 0.31995 (17) | 0.0449 (8) | |
C9 | 0.2329 (6) | 1.2247 (3) | 0.2628 (2) | 0.0683 (11) | |
H9A | 0.1300 | 1.2411 | 0.2886 | 0.102* | |
H9B | 0.1972 | 1.2527 | 0.2154 | 0.102* | |
H9C | 0.3482 | 1.2654 | 0.2845 | 0.102* | |
C10 | 0.1887 (5) | 0.6050 (3) | 0.40943 (18) | 0.0514 (8) | |
C11 | 0.1974 (7) | 0.4721 (3) | 0.4029 (3) | 0.0998 (17) | |
H11A | 0.2733 | 0.4392 | 0.4444 | 0.150* | |
H11B | 0.2556 | 0.4516 | 0.3628 | 0.150* | |
H11C | 0.0689 | 0.4396 | 0.3972 | 0.150* | |
Cu1 | 0.29526 (5) | 0.83205 (3) | 0.421912 (18) | 0.03645 (15) | |
N1 | 0.2877 (4) | 0.8369 (2) | 0.52489 (12) | 0.0373 (6) | |
N2 | 0.2604 (3) | 1.0043 (2) | 0.43270 (12) | 0.0342 (5) | |
N3 | 0.2540 (4) | 1.0847 (2) | 0.37953 (12) | 0.0407 (6) | |
N4 | 0.2682 (4) | 1.0967 (2) | 0.26244 (14) | 0.0546 (7) | |
O1 | 0.3493 (3) | 0.66081 (18) | 0.41619 (12) | 0.0476 (6) | |
O2 | 0.0355 (3) | 0.6581 (2) | 0.40896 (14) | 0.0624 (7) | |
O3 | 0.6802 (5) | 0.5407 (3) | 0.38013 (17) | 0.0597 (8) | |
S1 | 0.31034 (15) | 0.87631 (8) | 0.31082 (4) | 0.0560 (3) | |
H3A | 0.587 (7) | 0.582 (4) | 0.395 (2) | 0.105 (18)* | |
H3B | 0.753 (6) | 0.569 (4) | 0.395 (2) | 0.046 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.047 (2) | 0.047 (2) | 0.050 (2) | 0.0000 (15) | 0.0028 (15) | 0.0049 (15) |
C2 | 0.063 (2) | 0.068 (3) | 0.045 (2) | −0.0067 (19) | 0.0041 (17) | 0.0168 (18) |
C3 | 0.063 (2) | 0.091 (3) | 0.0349 (18) | −0.014 (2) | 0.0110 (16) | −0.0020 (19) |
C4 | 0.0470 (19) | 0.060 (2) | 0.0431 (18) | −0.0060 (16) | 0.0121 (15) | −0.0115 (16) |
C5 | 0.0273 (15) | 0.0450 (18) | 0.0396 (16) | −0.0042 (13) | 0.0032 (12) | −0.0053 (13) |
C6 | 0.0276 (15) | 0.0354 (16) | 0.0446 (17) | 0.0000 (12) | 0.0048 (13) | −0.0091 (13) |
C7 | 0.051 (2) | 0.0399 (18) | 0.063 (2) | 0.0040 (15) | 0.0128 (16) | −0.0146 (16) |
C8 | 0.0420 (18) | 0.0440 (19) | 0.0471 (18) | −0.0026 (14) | 0.0023 (14) | 0.0005 (15) |
C9 | 0.079 (3) | 0.061 (2) | 0.063 (2) | 0.002 (2) | 0.006 (2) | 0.0194 (19) |
C10 | 0.054 (2) | 0.0364 (19) | 0.064 (2) | −0.0019 (17) | 0.0118 (17) | −0.0104 (16) |
C11 | 0.079 (3) | 0.041 (2) | 0.183 (5) | −0.002 (2) | 0.030 (3) | −0.026 (3) |
Cu1 | 0.0383 (2) | 0.0310 (2) | 0.0401 (2) | 0.00123 (15) | 0.00642 (16) | −0.00521 (15) |
N1 | 0.0373 (14) | 0.0392 (14) | 0.0345 (13) | 0.0002 (11) | 0.0039 (11) | 0.0012 (11) |
N2 | 0.0331 (13) | 0.0303 (13) | 0.0392 (14) | 0.0004 (10) | 0.0056 (10) | −0.0025 (10) |
N3 | 0.0446 (15) | 0.0363 (14) | 0.0406 (14) | 0.0028 (12) | 0.0051 (12) | 0.0026 (11) |
N4 | 0.0654 (19) | 0.0496 (17) | 0.0474 (16) | −0.0008 (15) | 0.0048 (14) | 0.0143 (13) |
O1 | 0.0403 (13) | 0.0349 (12) | 0.0694 (16) | 0.0000 (10) | 0.0143 (11) | −0.0080 (10) |
O2 | 0.0417 (14) | 0.0517 (15) | 0.094 (2) | 0.0011 (11) | 0.0123 (13) | −0.0200 (13) |
O3 | 0.0498 (18) | 0.0539 (17) | 0.077 (2) | −0.0018 (15) | 0.0159 (16) | −0.0153 (14) |
S1 | 0.0848 (7) | 0.0446 (5) | 0.0402 (5) | −0.0016 (5) | 0.0155 (4) | −0.0079 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.328 (4) | C9—N4 | 1.445 (4) |
C1—C2 | 1.367 (5) | C9—H9A | 0.9600 |
C1—H1 | 0.9300 | C9—H9B | 0.9600 |
C2—C3 | 1.354 (5) | C9—H9C | 0.9600 |
C2—H2 | 0.9300 | C10—O2 | 1.224 (4) |
C3—C4 | 1.377 (5) | C10—O1 | 1.273 (4) |
C3—H3 | 0.9300 | C10—C11 | 1.485 (5) |
C4—C5 | 1.380 (4) | C11—H11A | 0.9600 |
C4—H4 | 0.9300 | C11—H11B | 0.9600 |
C5—N1 | 1.347 (4) | C11—H11C | 0.9600 |
C5—C6 | 1.466 (4) | Cu1—N2 | 1.945 (2) |
C6—N2 | 1.290 (4) | Cu1—O1 | 1.948 (2) |
C6—C7 | 1.479 (4) | Cu1—N1 | 2.001 (2) |
C7—H7A | 0.9600 | Cu1—S1 | 2.2230 (11) |
C7—H7B | 0.9600 | Cu1—O2 | 2.639 (13) |
C7—H7C | 0.9600 | N2—N3 | 1.358 (3) |
C8—N3 | 1.328 (4) | O3—H3A | 0.88 (5) |
C8—N4 | 1.329 (4) | O3—H3B | 0.63 (4) |
C8—S1 | 1.745 (3) | | |
| | | |
N1—C1—C2 | 122.2 (3) | N4—C9—H9C | 109.5 |
N1—C1—H1 | 118.9 | H9A—C9—H9C | 109.5 |
C2—C1—H1 | 118.9 | H9B—C9—H9C | 109.5 |
C3—C2—C1 | 119.0 (3) | O2—C10—O1 | 121.7 (3) |
C3—C2—H2 | 120.5 | O2—C10—C11 | 121.8 (3) |
C1—C2—H2 | 120.5 | O1—C10—C11 | 116.5 (3) |
C2—C3—C4 | 120.1 (3) | C10—C11—H11A | 109.5 |
C2—C3—H3 | 120.0 | C10—C11—H11B | 109.5 |
C4—C3—H3 | 120.0 | H11A—C11—H11B | 109.5 |
C3—C4—C5 | 118.6 (3) | C10—C11—H11C | 109.5 |
C3—C4—H4 | 120.7 | H11A—C11—H11C | 109.5 |
C5—C4—H4 | 120.7 | H11B—C11—H11C | 109.5 |
N1—C5—C4 | 120.9 (3) | N2—Cu1—O1 | 175.50 (9) |
N1—C5—C6 | 114.8 (3) | N2—Cu1—N1 | 80.93 (9) |
C4—C5—C6 | 124.2 (3) | O1—Cu1—N1 | 96.90 (10) |
N2—C6—C5 | 114.2 (3) | N2—Cu1—S1 | 84.98 (7) |
N2—C6—C7 | 123.2 (3) | O1—Cu1—S1 | 96.94 (7) |
C5—C6—C7 | 122.6 (3) | N1—Cu1—S1 | 165.61 (7) |
C6—C7—H7A | 109.5 | C1—N1—C5 | 119.3 (3) |
C6—C7—H7B | 109.5 | C1—N1—Cu1 | 128.0 (2) |
H7A—C7—H7B | 109.5 | C5—N1—Cu1 | 112.61 (19) |
C6—C7—H7C | 109.5 | C6—N2—N3 | 118.9 (2) |
H7A—C7—H7C | 109.5 | C6—N2—Cu1 | 117.3 (2) |
H7B—C7—H7C | 109.5 | N3—N2—Cu1 | 123.79 (18) |
N3—C8—N4 | 118.7 (3) | C8—N3—N2 | 111.2 (2) |
N3—C8—S1 | 124.9 (2) | C8—N4—C9 | 121.6 (3) |
N4—C8—S1 | 116.4 (3) | C10—O1—Cu1 | 107.8 (2) |
N4—C9—H9A | 109.5 | H3A—O3—H3B | 100 (5) |
N4—C9—H9B | 109.5 | C8—S1—Cu1 | 95.09 (11) |
H9A—C9—H9B | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···O2i | 0.63 (4) | 2.19 (4) | 2.786 (4) | 160 (5) |
O3—H3A···O1 | 0.88 (5) | 1.99 (5) | 2.860 (4) | 171 (4) |
Symmetry code: (i) x+1, y, z. |
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