In the structure of the title complex, [Cu(C2H3O2)(NCS)(C10H9N3)(H2O)], the CuII atom displays a square-pyramidal geometry, coordinated by two N atoms of the di-2-pyridylamine ligand, the N atom from the isothiocyanate ligand and two O atoms from the acetate group and the water molecule. The structure displays intermolecular hydrogen bonding.
Supporting information
CCDC reference: 618344
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.020
- wR factor = 0.051
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 8
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N4 .. 6.96 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
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 30.40
From the CIF: _reflns_number_total 4384
Count of symmetry unique reflns 2718
Completeness (_total/calc) 161.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1666
Fraction of Friedel pairs measured 0.613
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
2 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 (Sheldrick, 2000b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Acetatoaqua(di-2-pyridylamine)isothiocyanatocopper(II)
top
Crystal data top
[Cu(C2H3O2)(NCS)(C10H9N3)(H2O)] | F(000) = 756 |
Mr = 369.88 | Dx = 1.555 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4384 reflections |
a = 6.9742 (1) Å | θ = 2.4–30.4° |
b = 13.2883 (1) Å | µ = 1.53 mm−1 |
c = 17.0472 (2) Å | T = 273 K |
V = 1579.85 (3) Å3 | Rod, green |
Z = 4 | 0.48 × 0.30 × 0.23 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 4384 independent reflections |
Radiation source: fine-focus sealed tube | 4133 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 30.4°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000a) | h = −9→9 |
Tmin = 0.596, Tmax = 0.709 | k = −15→18 |
11607 measured reflections | l = −20→23 |
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)] = 0.020 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.051 | w = 1/[σ2(Fo2) + (0.0328P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4384 reflections | Δρmax = 0.24 e Å−3 |
255 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.20 (2) |
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 | |
C12 | −0.1526 (2) | 0.31682 (10) | 0.23769 (7) | 0.0328 (3) | |
O1 | 0.02113 (15) | 0.34083 (9) | 0.22978 (6) | 0.0382 (2) | |
C13 | −0.2141 (3) | 0.28586 (17) | 0.31925 (10) | 0.0566 (5) | |
H14 | −0.3379 | 0.3140 | 0.3305 | 0.085* | |
H13 | −0.1226 | 0.3101 | 0.3568 | 0.085* | |
H15 | −0.2210 | 0.2138 | 0.3222 | 0.085* | |
O2 | −0.27317 (18) | 0.31615 (10) | 0.18350 (7) | 0.0475 (3) | |
N4 | −0.0223 (2) | 0.51854 (11) | 0.14836 (10) | 0.0499 (4) | |
C11 | −0.1544 (2) | 0.56957 (11) | 0.14017 (9) | 0.0397 (3) | |
O3 | 0.40137 (19) | 0.43699 (13) | 0.19022 (8) | 0.0492 (3) | |
S1 | −0.33948 (7) | 0.64227 (4) | 0.12887 (4) | 0.06453 (13) | |
Cu1 | 0.12034 (2) | 0.391979 (12) | 0.129773 (9) | 0.03095 (5) | |
N3 | 0.1769 (2) | 0.28389 (11) | −0.03829 (7) | 0.0381 (3) | |
N2 | 0.20470 (18) | 0.44243 (10) | 0.02384 (7) | 0.0344 (2) | |
C4 | 0.2079 (2) | 0.11464 (13) | 0.00637 (9) | 0.0413 (3) | |
N1 | 0.19903 (18) | 0.25193 (9) | 0.09834 (7) | 0.0340 (2) | |
C5 | 0.1945 (2) | 0.21821 (11) | 0.02458 (8) | 0.0326 (3) | |
C6 | 0.20767 (19) | 0.38649 (13) | −0.04124 (7) | 0.0348 (3) | |
C1 | 0.2341 (2) | 0.18329 (13) | 0.15624 (10) | 0.0431 (3) | |
C8 | 0.2707 (3) | 0.53031 (16) | −0.12216 (11) | 0.0562 (5) | |
C2 | 0.2562 (3) | 0.08292 (13) | 0.14242 (11) | 0.0505 (4) | |
C10 | 0.2410 (3) | 0.54260 (13) | 0.01664 (11) | 0.0455 (4) | |
C9 | 0.2743 (3) | 0.58885 (15) | −0.05433 (12) | 0.0555 (4) | |
C3 | 0.2386 (3) | 0.04714 (14) | 0.06595 (12) | 0.0496 (4) | |
C7 | 0.2387 (3) | 0.42981 (15) | −0.11578 (9) | 0.0463 (4) | |
H4 | 0.202 (3) | 0.0896 (15) | −0.0454 (12) | 0.049 (5)* | |
H12W | 0.489 (4) | 0.397 (2) | 0.1903 (14) | 0.059 (7)* | |
H2 | 0.291 (4) | 0.0423 (19) | 0.1845 (16) | 0.072 (7)* | |
H5 | 0.196 (3) | 0.2559 (15) | −0.0835 (13) | 0.047 (5)* | |
H10 | 0.246 (3) | 0.5843 (15) | 0.0668 (12) | 0.049 (5)* | |
H7 | 0.236 (3) | 0.3899 (16) | −0.1578 (12) | 0.052 (5)* | |
H11W | 0.441 (4) | 0.488 (2) | 0.1772 (18) | 0.077 (9)* | |
H8 | 0.292 (3) | 0.5595 (18) | −0.1694 (13) | 0.058 (6)* | |
H3 | 0.252 (3) | −0.0236 (15) | 0.0537 (12) | 0.044 (5)* | |
H1 | 0.247 (3) | 0.2096 (16) | 0.2017 (13) | 0.047 (5)* | |
H9 | 0.296 (4) | 0.6531 (19) | −0.0590 (14) | 0.067 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C12 | 0.0380 (7) | 0.0323 (6) | 0.0281 (6) | 0.0001 (5) | 0.0044 (5) | −0.0029 (5) |
O1 | 0.0357 (5) | 0.0496 (6) | 0.0292 (5) | 0.0006 (4) | 0.0040 (4) | 0.0014 (4) |
C13 | 0.0597 (11) | 0.0720 (12) | 0.0382 (8) | −0.0140 (10) | 0.0095 (8) | 0.0080 (8) |
O2 | 0.0459 (6) | 0.0580 (7) | 0.0387 (6) | −0.0027 (6) | −0.0075 (5) | −0.0084 (5) |
N4 | 0.0530 (9) | 0.0434 (7) | 0.0532 (9) | 0.0068 (6) | 0.0148 (7) | −0.0008 (6) |
C11 | 0.0462 (8) | 0.0320 (6) | 0.0410 (7) | −0.0024 (5) | 0.0070 (6) | −0.0049 (5) |
O3 | 0.0355 (6) | 0.0612 (8) | 0.0509 (6) | −0.0030 (6) | −0.0031 (5) | −0.0028 (6) |
S1 | 0.0537 (3) | 0.0490 (2) | 0.0910 (4) | 0.00975 (18) | −0.0104 (3) | −0.0006 (2) |
Cu1 | 0.03062 (7) | 0.03583 (7) | 0.02639 (7) | 0.00165 (6) | 0.00321 (6) | −0.00089 (6) |
N3 | 0.0426 (7) | 0.0454 (7) | 0.0261 (6) | 0.0002 (5) | 0.0007 (4) | −0.0029 (5) |
N2 | 0.0347 (6) | 0.0382 (6) | 0.0305 (5) | −0.0003 (5) | 0.0016 (4) | 0.0033 (4) |
C4 | 0.0399 (7) | 0.0427 (7) | 0.0414 (7) | −0.0012 (6) | 0.0065 (6) | −0.0079 (7) |
N1 | 0.0349 (6) | 0.0383 (6) | 0.0287 (5) | 0.0045 (5) | 0.0027 (4) | 0.0008 (4) |
C5 | 0.0259 (6) | 0.0407 (7) | 0.0311 (6) | 0.0014 (5) | 0.0043 (5) | −0.0022 (5) |
C6 | 0.0270 (6) | 0.0480 (7) | 0.0293 (6) | 0.0010 (6) | 0.0010 (4) | 0.0027 (6) |
C1 | 0.0489 (9) | 0.0468 (9) | 0.0334 (7) | 0.0102 (7) | 0.0027 (6) | 0.0030 (6) |
C8 | 0.0561 (10) | 0.0708 (12) | 0.0418 (9) | −0.0053 (9) | 0.0045 (8) | 0.0251 (9) |
C2 | 0.0591 (10) | 0.0435 (8) | 0.0488 (10) | 0.0097 (7) | 0.0060 (8) | 0.0114 (7) |
C10 | 0.0476 (9) | 0.0424 (8) | 0.0466 (9) | −0.0047 (7) | 0.0050 (7) | 0.0046 (7) |
C9 | 0.0633 (11) | 0.0459 (10) | 0.0573 (10) | −0.0072 (8) | 0.0028 (9) | 0.0166 (8) |
C3 | 0.0534 (10) | 0.0363 (8) | 0.0591 (11) | 0.0028 (7) | 0.0101 (8) | −0.0022 (7) |
C7 | 0.0462 (8) | 0.0639 (10) | 0.0288 (7) | −0.0031 (7) | 0.0020 (6) | 0.0077 (6) |
Geometric parameters (Å, º) top
C12—O2 | 1.2493 (18) | N2—C10 | 1.361 (2) |
C12—O1 | 1.2600 (18) | C4—C3 | 1.372 (3) |
C12—C13 | 1.512 (2) | C4—C5 | 1.414 (2) |
O1—Cu1 | 1.9615 (10) | C4—H4 | 0.94 (2) |
C13—H14 | 0.9600 | N1—C5 | 1.3351 (18) |
C13—H13 | 0.9600 | N1—C1 | 1.366 (2) |
C13—H15 | 0.9501 | C6—C7 | 1.412 (2) |
N4—C11 | 1.153 (2) | C1—C2 | 1.363 (2) |
N4—Cu1 | 1.9794 (14) | C1—H1 | 0.86 (2) |
C11—S1 | 1.6237 (16) | C8—C7 | 1.358 (3) |
O3—Cu1 | 2.2937 (13) | C8—C9 | 1.394 (3) |
O3—H12W | 0.81 (3) | C8—H8 | 0.91 (2) |
O3—H11W | 0.76 (3) | C2—C3 | 1.393 (3) |
Cu1—N1 | 2.0129 (12) | C2—H2 | 0.93 (3) |
Cu1—N2 | 2.0141 (12) | C10—C9 | 1.377 (3) |
N3—C6 | 1.381 (2) | C10—H10 | 1.02 (2) |
N3—C5 | 1.3876 (18) | C9—H9 | 0.87 (2) |
N3—H5 | 0.87 (2) | C3—H3 | 0.97 (2) |
N2—C6 | 1.3356 (19) | C7—H7 | 0.89 (2) |
| | | |
O2—C12—O1 | 124.74 (13) | C3—C4—H4 | 117.9 (12) |
O2—C12—C13 | 119.14 (14) | C5—C4—H4 | 123.1 (12) |
O1—C12—C13 | 116.11 (14) | C5—N1—C1 | 117.43 (13) |
C12—O1—Cu1 | 121.33 (9) | C5—N1—Cu1 | 123.68 (10) |
C12—C13—H14 | 109.5 | C1—N1—Cu1 | 118.28 (10) |
C12—C13—H13 | 109.5 | N1—C5—N3 | 121.22 (13) |
H14—C13—H13 | 109.5 | N1—C5—C4 | 122.13 (14) |
C12—C13—H15 | 109.5 | N3—C5—C4 | 116.64 (13) |
H14—C13—H15 | 109.5 | N2—C6—N3 | 121.11 (12) |
H13—C13—H15 | 109.5 | N2—C6—C7 | 121.54 (15) |
C11—N4—Cu1 | 151.91 (15) | N3—C6—C7 | 117.34 (14) |
N4—C11—S1 | 179.51 (17) | C2—C1—N1 | 123.27 (16) |
Cu1—O3—H12W | 118.4 (18) | C2—C1—H1 | 123.0 (14) |
Cu1—O3—H11W | 114 (2) | N1—C1—H1 | 113.7 (14) |
H12W—O3—H11W | 108 (3) | C7—C8—C9 | 119.02 (16) |
O1—Cu1—N4 | 88.74 (6) | C7—C8—H8 | 121.3 (15) |
O1—Cu1—N1 | 90.41 (5) | C9—C8—H8 | 119.7 (15) |
N4—Cu1—N1 | 164.83 (6) | C1—C2—C3 | 119.07 (16) |
O1—Cu1—N2 | 176.11 (5) | C1—C2—H2 | 117.6 (16) |
N4—Cu1—N2 | 90.43 (6) | C3—C2—H2 | 123.2 (16) |
N1—Cu1—N2 | 89.39 (5) | N2—C10—C9 | 123.18 (18) |
O1—Cu1—O3 | 90.07 (5) | N2—C10—H10 | 117.6 (11) |
N4—Cu1—O3 | 97.81 (7) | C9—C10—H10 | 119.2 (11) |
N1—Cu1—O3 | 97.34 (6) | C10—C9—C8 | 118.49 (18) |
N2—Cu1—O3 | 93.81 (5) | C10—C9—H9 | 123.2 (16) |
C6—N3—C5 | 129.45 (12) | C8—C9—H9 | 118.3 (16) |
C6—N3—H5 | 111.5 (13) | C4—C3—C2 | 118.90 (16) |
C5—N3—H5 | 113.9 (13) | C4—C3—H3 | 119.3 (12) |
C6—N2—C10 | 117.82 (14) | C2—C3—H3 | 121.7 (12) |
C6—N2—Cu1 | 124.34 (10) | C8—C7—C6 | 119.88 (17) |
C10—N2—Cu1 | 117.44 (11) | C8—C7—H7 | 121.5 (14) |
C3—C4—C5 | 118.96 (15) | C6—C7—H7 | 118.6 (14) |
| | | |
O2—C12—O1—Cu1 | 5.1 (2) | C1—N1—C5—C4 | 5.6 (2) |
C13—C12—O1—Cu1 | −175.59 (11) | Cu1—N1—C5—C4 | −165.26 (11) |
C12—O1—Cu1—N4 | 71.31 (12) | C6—N3—C5—N1 | 17.4 (2) |
C12—O1—Cu1—N1 | −93.54 (12) | C6—N3—C5—C4 | −162.32 (15) |
C12—O1—Cu1—O3 | 169.12 (12) | C3—C4—C5—N1 | −4.1 (2) |
C11—N4—Cu1—O1 | −95.7 (3) | C3—C4—C5—N3 | 175.62 (15) |
C11—N4—Cu1—N1 | −8.7 (5) | C10—N2—C6—N3 | 178.37 (14) |
C11—N4—Cu1—N2 | 80.5 (3) | Cu1—N2—C6—N3 | −9.07 (19) |
C11—N4—Cu1—O3 | 174.4 (3) | C10—N2—C6—C7 | −2.8 (2) |
N4—Cu1—N2—C6 | −137.56 (12) | Cu1—N2—C6—C7 | 169.73 (11) |
N1—Cu1—N2—C6 | 27.26 (12) | C5—N3—C6—N2 | −20.7 (2) |
O3—Cu1—N2—C6 | 124.58 (12) | C5—N3—C6—C7 | 160.45 (15) |
N4—Cu1—N2—C10 | 35.03 (13) | C5—N1—C1—C2 | −2.8 (2) |
N1—Cu1—N2—C10 | −160.15 (12) | Cu1—N1—C1—C2 | 168.52 (15) |
O3—Cu1—N2—C10 | −62.83 (13) | N1—C1—C2—C3 | −1.4 (3) |
O1—Cu1—N1—C5 | 146.00 (12) | C6—N2—C10—C9 | 2.1 (3) |
N4—Cu1—N1—C5 | 59.3 (3) | Cu1—N2—C10—C9 | −170.98 (15) |
N2—Cu1—N1—C5 | −30.11 (12) | N2—C10—C9—C8 | 0.0 (3) |
O3—Cu1—N1—C5 | −123.88 (12) | C7—C8—C9—C10 | −1.4 (3) |
O1—Cu1—N1—C1 | −24.76 (12) | C5—C4—C3—C2 | −0.3 (3) |
N4—Cu1—N1—C1 | −111.5 (2) | C1—C2—C3—C4 | 2.9 (3) |
N2—Cu1—N1—C1 | 159.13 (12) | C9—C8—C7—C6 | 0.7 (3) |
O3—Cu1—N1—C1 | 65.36 (12) | N2—C6—C7—C8 | 1.5 (2) |
C1—N1—C5—N3 | −174.18 (14) | N3—C6—C7—C8 | −179.65 (16) |
Cu1—N1—C5—N3 | 14.99 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H12W···O2i | 0.81 (3) | 1.98 (3) | 2.782 (3) | 171 (4) |
O3—H11W···S1i | 0.77 (3) | 2.72 (2) | 3.436 (3) | 166 (4) |
N3—H5···O2ii | 0.87 (1) | 1.96 (1) | 2.831 (2) | 176 (1) |
C8—H8···O1iii | 0.93 (1) | 2.52 (1) | 3.378 (1) | 155 (1) |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z; (iii) −x+1/2, −y+1, z−1/2. |