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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025803/xu2057sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025803/xu2057Isup2.hkl
Contains datablock I

CCDC reference: 618344

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.020
  • wR factor = 0.051
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

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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

Computing details top

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 = 369.88Dx = 1.555 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4384 reflections
a = 6.9742 (1) Åθ = 2.4–30.4°
b = 13.2883 (1) ŵ = 1.53 mm1
c = 17.0472 (2) ÅT = 273 K
V = 1579.85 (3) Å3Rod, green
Z = 40.48 × 0.30 × 0.23 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
4384 independent reflections
Radiation source: fine-focus sealed tube4133 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 30.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000a)
h = 99
Tmin = 0.596, Tmax = 0.709k = 1518
11607 measured reflectionsl = 2023
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H 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 reflectionsΔρmax = 0.24 e Å3
255 parametersΔρmin = 0.27 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
C120.1526 (2)0.31682 (10)0.23769 (7)0.0328 (3)
O10.02113 (15)0.34083 (9)0.22978 (6)0.0382 (2)
C130.2141 (3)0.28586 (17)0.31925 (10)0.0566 (5)
H140.33790.31400.33050.085*
H130.12260.31010.35680.085*
H150.22100.21380.32220.085*
O20.27317 (18)0.31615 (10)0.18350 (7)0.0475 (3)
N40.0223 (2)0.51854 (11)0.14836 (10)0.0499 (4)
C110.1544 (2)0.56957 (11)0.14017 (9)0.0397 (3)
O30.40137 (19)0.43699 (13)0.19022 (8)0.0492 (3)
S10.33948 (7)0.64227 (4)0.12887 (4)0.06453 (13)
Cu10.12034 (2)0.391979 (12)0.129773 (9)0.03095 (5)
N30.1769 (2)0.28389 (11)0.03829 (7)0.0381 (3)
N20.20470 (18)0.44243 (10)0.02384 (7)0.0344 (2)
C40.2079 (2)0.11464 (13)0.00637 (9)0.0413 (3)
N10.19903 (18)0.25193 (9)0.09834 (7)0.0340 (2)
C50.1945 (2)0.21821 (11)0.02458 (8)0.0326 (3)
C60.20767 (19)0.38649 (13)0.04124 (7)0.0348 (3)
C10.2341 (2)0.18329 (13)0.15624 (10)0.0431 (3)
C80.2707 (3)0.53031 (16)0.12216 (11)0.0562 (5)
C20.2562 (3)0.08292 (13)0.14242 (11)0.0505 (4)
C100.2410 (3)0.54260 (13)0.01664 (11)0.0455 (4)
C90.2743 (3)0.58885 (15)0.05433 (12)0.0555 (4)
C30.2386 (3)0.04714 (14)0.06595 (12)0.0496 (4)
C70.2387 (3)0.42981 (15)0.11578 (9)0.0463 (4)
H40.202 (3)0.0896 (15)0.0454 (12)0.049 (5)*
H12W0.489 (4)0.397 (2)0.1903 (14)0.059 (7)*
H20.291 (4)0.0423 (19)0.1845 (16)0.072 (7)*
H50.196 (3)0.2559 (15)0.0835 (13)0.047 (5)*
H100.246 (3)0.5843 (15)0.0668 (12)0.049 (5)*
H70.236 (3)0.3899 (16)0.1578 (12)0.052 (5)*
H11W0.441 (4)0.488 (2)0.1772 (18)0.077 (9)*
H80.292 (3)0.5595 (18)0.1694 (13)0.058 (6)*
H30.252 (3)0.0236 (15)0.0537 (12)0.044 (5)*
H10.247 (3)0.2096 (16)0.2017 (13)0.047 (5)*
H90.296 (4)0.6531 (19)0.0590 (14)0.067 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.0380 (7)0.0323 (6)0.0281 (6)0.0001 (5)0.0044 (5)0.0029 (5)
O10.0357 (5)0.0496 (6)0.0292 (5)0.0006 (4)0.0040 (4)0.0014 (4)
C130.0597 (11)0.0720 (12)0.0382 (8)0.0140 (10)0.0095 (8)0.0080 (8)
O20.0459 (6)0.0580 (7)0.0387 (6)0.0027 (6)0.0075 (5)0.0084 (5)
N40.0530 (9)0.0434 (7)0.0532 (9)0.0068 (6)0.0148 (7)0.0008 (6)
C110.0462 (8)0.0320 (6)0.0410 (7)0.0024 (5)0.0070 (6)0.0049 (5)
O30.0355 (6)0.0612 (8)0.0509 (6)0.0030 (6)0.0031 (5)0.0028 (6)
S10.0537 (3)0.0490 (2)0.0910 (4)0.00975 (18)0.0104 (3)0.0006 (2)
Cu10.03062 (7)0.03583 (7)0.02639 (7)0.00165 (6)0.00321 (6)0.00089 (6)
N30.0426 (7)0.0454 (7)0.0261 (6)0.0002 (5)0.0007 (4)0.0029 (5)
N20.0347 (6)0.0382 (6)0.0305 (5)0.0003 (5)0.0016 (4)0.0033 (4)
C40.0399 (7)0.0427 (7)0.0414 (7)0.0012 (6)0.0065 (6)0.0079 (7)
N10.0349 (6)0.0383 (6)0.0287 (5)0.0045 (5)0.0027 (4)0.0008 (4)
C50.0259 (6)0.0407 (7)0.0311 (6)0.0014 (5)0.0043 (5)0.0022 (5)
C60.0270 (6)0.0480 (7)0.0293 (6)0.0010 (6)0.0010 (4)0.0027 (6)
C10.0489 (9)0.0468 (9)0.0334 (7)0.0102 (7)0.0027 (6)0.0030 (6)
C80.0561 (10)0.0708 (12)0.0418 (9)0.0053 (9)0.0045 (8)0.0251 (9)
C20.0591 (10)0.0435 (8)0.0488 (10)0.0097 (7)0.0060 (8)0.0114 (7)
C100.0476 (9)0.0424 (8)0.0466 (9)0.0047 (7)0.0050 (7)0.0046 (7)
C90.0633 (11)0.0459 (10)0.0573 (10)0.0072 (8)0.0028 (9)0.0166 (8)
C30.0534 (10)0.0363 (8)0.0591 (11)0.0028 (7)0.0101 (8)0.0022 (7)
C70.0462 (8)0.0639 (10)0.0288 (7)0.0031 (7)0.0020 (6)0.0077 (6)
Geometric parameters (Å, º) top
C12—O21.2493 (18)N2—C101.361 (2)
C12—O11.2600 (18)C4—C31.372 (3)
C12—C131.512 (2)C4—C51.414 (2)
O1—Cu11.9615 (10)C4—H40.94 (2)
C13—H140.9600N1—C51.3351 (18)
C13—H130.9600N1—C11.366 (2)
C13—H150.9501C6—C71.412 (2)
N4—C111.153 (2)C1—C21.363 (2)
N4—Cu11.9794 (14)C1—H10.86 (2)
C11—S11.6237 (16)C8—C71.358 (3)
O3—Cu12.2937 (13)C8—C91.394 (3)
O3—H12W0.81 (3)C8—H80.91 (2)
O3—H11W0.76 (3)C2—C31.393 (3)
Cu1—N12.0129 (12)C2—H20.93 (3)
Cu1—N22.0141 (12)C10—C91.377 (3)
N3—C61.381 (2)C10—H101.02 (2)
N3—C51.3876 (18)C9—H90.87 (2)
N3—H50.87 (2)C3—H30.97 (2)
N2—C61.3356 (19)C7—H70.89 (2)
O2—C12—O1124.74 (13)C3—C4—H4117.9 (12)
O2—C12—C13119.14 (14)C5—C4—H4123.1 (12)
O1—C12—C13116.11 (14)C5—N1—C1117.43 (13)
C12—O1—Cu1121.33 (9)C5—N1—Cu1123.68 (10)
C12—C13—H14109.5C1—N1—Cu1118.28 (10)
C12—C13—H13109.5N1—C5—N3121.22 (13)
H14—C13—H13109.5N1—C5—C4122.13 (14)
C12—C13—H15109.5N3—C5—C4116.64 (13)
H14—C13—H15109.5N2—C6—N3121.11 (12)
H13—C13—H15109.5N2—C6—C7121.54 (15)
C11—N4—Cu1151.91 (15)N3—C6—C7117.34 (14)
N4—C11—S1179.51 (17)C2—C1—N1123.27 (16)
Cu1—O3—H12W118.4 (18)C2—C1—H1123.0 (14)
Cu1—O3—H11W114 (2)N1—C1—H1113.7 (14)
H12W—O3—H11W108 (3)C7—C8—C9119.02 (16)
O1—Cu1—N488.74 (6)C7—C8—H8121.3 (15)
O1—Cu1—N190.41 (5)C9—C8—H8119.7 (15)
N4—Cu1—N1164.83 (6)C1—C2—C3119.07 (16)
O1—Cu1—N2176.11 (5)C1—C2—H2117.6 (16)
N4—Cu1—N290.43 (6)C3—C2—H2123.2 (16)
N1—Cu1—N289.39 (5)N2—C10—C9123.18 (18)
O1—Cu1—O390.07 (5)N2—C10—H10117.6 (11)
N4—Cu1—O397.81 (7)C9—C10—H10119.2 (11)
N1—Cu1—O397.34 (6)C10—C9—C8118.49 (18)
N2—Cu1—O393.81 (5)C10—C9—H9123.2 (16)
C6—N3—C5129.45 (12)C8—C9—H9118.3 (16)
C6—N3—H5111.5 (13)C4—C3—C2118.90 (16)
C5—N3—H5113.9 (13)C4—C3—H3119.3 (12)
C6—N2—C10117.82 (14)C2—C3—H3121.7 (12)
C6—N2—Cu1124.34 (10)C8—C7—C6119.88 (17)
C10—N2—Cu1117.44 (11)C8—C7—H7121.5 (14)
C3—C4—C5118.96 (15)C6—C7—H7118.6 (14)
O2—C12—O1—Cu15.1 (2)C1—N1—C5—C45.6 (2)
C13—C12—O1—Cu1175.59 (11)Cu1—N1—C5—C4165.26 (11)
C12—O1—Cu1—N471.31 (12)C6—N3—C5—N117.4 (2)
C12—O1—Cu1—N193.54 (12)C6—N3—C5—C4162.32 (15)
C12—O1—Cu1—O3169.12 (12)C3—C4—C5—N14.1 (2)
C11—N4—Cu1—O195.7 (3)C3—C4—C5—N3175.62 (15)
C11—N4—Cu1—N18.7 (5)C10—N2—C6—N3178.37 (14)
C11—N4—Cu1—N280.5 (3)Cu1—N2—C6—N39.07 (19)
C11—N4—Cu1—O3174.4 (3)C10—N2—C6—C72.8 (2)
N4—Cu1—N2—C6137.56 (12)Cu1—N2—C6—C7169.73 (11)
N1—Cu1—N2—C627.26 (12)C5—N3—C6—N220.7 (2)
O3—Cu1—N2—C6124.58 (12)C5—N3—C6—C7160.45 (15)
N4—Cu1—N2—C1035.03 (13)C5—N1—C1—C22.8 (2)
N1—Cu1—N2—C10160.15 (12)Cu1—N1—C1—C2168.52 (15)
O3—Cu1—N2—C1062.83 (13)N1—C1—C2—C31.4 (3)
O1—Cu1—N1—C5146.00 (12)C6—N2—C10—C92.1 (3)
N4—Cu1—N1—C559.3 (3)Cu1—N2—C10—C9170.98 (15)
N2—Cu1—N1—C530.11 (12)N2—C10—C9—C80.0 (3)
O3—Cu1—N1—C5123.88 (12)C7—C8—C9—C101.4 (3)
O1—Cu1—N1—C124.76 (12)C5—C4—C3—C20.3 (3)
N4—Cu1—N1—C1111.5 (2)C1—C2—C3—C42.9 (3)
N2—Cu1—N1—C1159.13 (12)C9—C8—C7—C60.7 (3)
O3—Cu1—N1—C165.36 (12)N2—C6—C7—C81.5 (2)
C1—N1—C5—N3174.18 (14)N3—C6—C7—C8179.65 (16)
Cu1—N1—C5—N314.99 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H12W···O2i0.81 (3)1.98 (3)2.782 (3)171 (4)
O3—H11W···S1i0.77 (3)2.72 (2)3.436 (3)166 (4)
N3—H5···O2ii0.87 (1)1.96 (1)2.831 (2)176 (1)
C8—H8···O1iii0.93 (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, z1/2.
 

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