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The title compound, [Cu(NCS)2(C12H19N3)], is a mononuclear copper(II) complex. The CuII ion is five-coordinated in a square-pyramidal configuration by three N atoms of the Schiff base ligand, and by two terminal N atoms from two thio­cyanate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010506/ci2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010506/ci2024Isup2.hkl
Contains datablock I

CCDC reference: 605020

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.044
  • wR factor = 0.108
  • Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C14
Author Response: This is caused by the disorder of the N5/C14/S2 moiety.

Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for N5
Author Response: This is probably caused by the long flexible propyl chain, which made the terminal C atoms of the cyclohexyl ring shifted to a certain extent.

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C13 .. 6.32 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C13 .. 5.46 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N4
Author Response: This is probably caused by the long flexible propyl chain, which made the terminal C atoms of the cyclohexyl ring shifted to a certain extent.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
Author Response: This is probably caused by the long flexible propyl chain, which made the terminal C atoms of the cyclohexyl ring shifted to a certain extent.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
Author Response: This is caused by the disorder of the N5/C14/S2 moiety.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
Author Response: This is caused by the disorder of the N5/C14/S2 moiety.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
Author Response: This is caused by the disorder of the N5/C14/S2 moiety.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C14 H19 Cu1 N5 S2 Atom count from _chemical_formula_moiety: 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 27.49 From the CIF: _reflns_number_total 4084 Count of symmetry unique reflns 2091 Completeness (_total/calc) 195.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1993 Fraction of Friedel pairs measured 0.953 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Cu(C12H19N3)(NCS)2]Dx = 1.433 Mg m3
Mr = 385.00Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 3609 reflections
Hall symbol: P 4wθ = 2.4–25.1°
a = 7.294 (1) ŵ = 1.46 mm1
c = 33.549 (3) ÅT = 298 K
V = 1784.9 (4) Å3Block, blue
Z = 40.35 × 0.12 × 0.10 mm
F(000) = 796
Data collection top
Bruker SMART CCD area-detector
diffractometer
4084 independent reflections
Radiation source: fine-focus sealed tube2778 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scanθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.629, Tmax = 0.868k = 99
15425 measured reflectionsl = 4343
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
4084 reflectionsΔρmax = 0.33 e Å3
201 parametersΔρmin = 0.24 e Å3
1 restraintAbsolute structure: Flack (1983); 1995 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.027 (15)
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
Cu10.92314 (7)0.04551 (6)0.796394 (14)0.07533 (17)
S10.6294 (2)0.57390 (17)0.75221 (4)0.1025 (4)
S21.2512 (3)0.4069 (3)0.89374 (6)0.1442 (7)
N10.7381 (5)0.0536 (5)0.83716 (10)0.0790 (9)
N21.0267 (6)0.1971 (5)0.80643 (12)0.0894 (11)
N31.0962 (4)0.0317 (5)0.74660 (13)0.0824 (10)
N40.7747 (6)0.2505 (6)0.78057 (12)0.1056 (15)
N51.1000 (8)0.1917 (8)0.83668 (17)0.1261 (17)
C10.5989 (7)0.0316 (8)0.85374 (14)0.0999 (14)
H10.57130.15070.84580.120*
C20.4911 (9)0.0529 (10)0.8831 (2)0.125 (2)
H20.39300.00870.89470.149*
C30.5323 (11)0.2226 (12)0.89397 (18)0.133 (2)
H30.46350.27880.91390.159*
C40.6749 (10)0.3183 (9)0.87647 (19)0.123 (2)
H40.70130.43860.88360.148*
C50.7764 (7)0.2265 (7)0.84790 (14)0.0871 (13)
C60.9371 (9)0.3015 (7)0.82880 (17)0.1013 (16)
H60.97270.42250.83290.122*
C71.1875 (9)0.2489 (8)0.7836 (2)0.122 (2)
H7A1.15670.34420.76460.146*
H7B1.28240.29510.80120.146*
C81.2552 (7)0.0763 (9)0.7617 (2)0.1126 (18)
H8A1.32710.00140.77980.135*
H8B1.33310.11160.73960.135*
C91.0083 (9)0.0708 (8)0.71385 (19)0.1080 (17)
H9A1.09390.07800.69180.130*
H9B0.98540.19510.72290.130*
C100.8348 (12)0.0061 (10)0.6989 (2)0.148 (3)
H10A0.74900.01620.72050.222*
H10B0.78530.07310.67880.222*
H10C0.85690.12530.68780.222*
C111.1598 (7)0.2181 (7)0.73486 (17)0.0951 (14)
H11A1.21360.27610.75810.114*
H11B1.05330.28980.72730.114*
C121.2982 (9)0.2277 (10)0.7009 (2)0.139 (2)
H12A1.41320.17770.70970.208*
H12B1.31510.35320.69310.208*
H12C1.25360.15830.67860.208*
C130.7145 (6)0.3850 (7)0.76873 (12)0.0775 (11)
C141.1606 (6)0.2808 (6)0.86033 (15)0.0781 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0768 (3)0.0713 (3)0.0779 (3)0.0230 (2)0.0049 (3)0.0022 (3)
S10.1163 (9)0.0879 (8)0.1032 (9)0.0377 (7)0.0080 (8)0.0079 (7)
S20.1579 (15)0.1175 (12)0.1573 (16)0.0130 (11)0.0253 (13)0.0358 (11)
N10.091 (2)0.083 (2)0.0633 (19)0.011 (2)0.0085 (18)0.0003 (17)
N20.104 (3)0.075 (2)0.089 (3)0.034 (2)0.009 (2)0.006 (2)
N30.069 (2)0.086 (2)0.092 (3)0.0060 (18)0.0052 (18)0.011 (2)
N40.099 (3)0.101 (3)0.117 (4)0.047 (2)0.000 (2)0.027 (2)
N50.138 (4)0.117 (4)0.124 (4)0.010 (3)0.042 (3)0.027 (3)
C10.098 (3)0.121 (4)0.081 (3)0.021 (3)0.010 (3)0.010 (3)
C20.103 (4)0.158 (6)0.112 (4)0.014 (4)0.009 (3)0.008 (4)
C30.140 (5)0.172 (7)0.086 (4)0.013 (5)0.016 (4)0.025 (4)
C40.162 (6)0.106 (4)0.103 (4)0.005 (4)0.010 (4)0.033 (4)
C50.107 (3)0.081 (3)0.074 (3)0.010 (3)0.010 (2)0.006 (2)
C60.138 (5)0.070 (3)0.096 (3)0.029 (3)0.023 (3)0.008 (3)
C70.114 (4)0.104 (4)0.148 (6)0.056 (3)0.005 (4)0.001 (4)
C80.077 (3)0.121 (4)0.140 (5)0.022 (3)0.003 (3)0.025 (4)
C90.101 (3)0.122 (4)0.101 (4)0.011 (3)0.013 (3)0.025 (3)
C100.170 (7)0.142 (5)0.132 (6)0.001 (5)0.069 (5)0.014 (4)
C110.094 (3)0.083 (3)0.109 (4)0.008 (3)0.013 (3)0.003 (3)
C120.121 (5)0.131 (5)0.164 (6)0.020 (4)0.044 (4)0.003 (5)
C130.069 (2)0.097 (3)0.066 (2)0.022 (2)0.0107 (19)0.001 (2)
C140.085 (3)0.065 (2)0.083 (3)0.005 (2)0.000 (2)0.002 (2)
Geometric parameters (Å, º) top
Cu1—N41.921 (4)C4—C51.384 (8)
Cu1—N21.954 (3)C4—H40.93
Cu1—N12.053 (4)C5—C61.444 (8)
Cu1—N32.096 (4)C6—H60.93
Cu1—N52.151 (5)C7—C81.540 (9)
S1—C131.610 (5)C7—H7A0.97
S2—C141.594 (5)C7—H7B0.97
N1—C11.314 (7)C8—H8A0.97
N1—C51.341 (6)C8—H8B0.97
N2—C61.253 (7)C9—C101.472 (9)
N2—C71.450 (7)C9—H9A0.97
N3—C91.476 (7)C9—H9B0.97
N3—C111.489 (6)C10—H10A0.96
N3—C81.491 (7)C10—H10B0.96
N4—C131.146 (5)C10—H10C0.96
N5—C141.117 (6)C11—C121.523 (8)
C1—C21.403 (8)C11—H11A0.97
C1—H10.93C11—H11B0.97
C2—C31.325 (9)C12—H12A0.96
C2—H20.93C12—H12B0.96
C3—C41.383 (10)C12—H12C0.96
C3—H30.93
N4—Cu1—N2166.1 (2)N2—C6—H6121.3
N4—Cu1—N195.02 (18)C5—C6—H6121.3
N2—Cu1—N179.66 (18)N2—C7—C8107.3 (4)
N4—Cu1—N399.01 (17)N2—C7—H7A110.3
N2—Cu1—N382.00 (17)C8—C7—H7A110.3
N1—Cu1—N3155.49 (15)N2—C7—H7B110.3
N4—Cu1—N597.2 (2)C8—C7—H7B110.3
N2—Cu1—N596.25 (19)H7A—C7—H7B108.5
N1—Cu1—N598.6 (2)N3—C8—C7110.2 (4)
N3—Cu1—N599.4 (2)N3—C8—H8A109.6
C1—N1—C5119.5 (5)C7—C8—H8A109.6
C1—N1—Cu1128.5 (3)N3—C8—H8B109.6
C5—N1—Cu1111.9 (3)C7—C8—H8B109.6
C6—N2—C7125.4 (4)H8A—C8—H8B108.1
C6—N2—Cu1116.9 (4)C10—C9—N3115.7 (5)
C7—N2—Cu1117.3 (4)C10—C9—H9A108.4
C9—N3—C11113.6 (4)N3—C9—H9A108.4
C9—N3—C8108.9 (4)C10—C9—H9B108.4
C11—N3—C8109.3 (4)N3—C9—H9B108.4
C9—N3—Cu1110.8 (3)H9A—C9—H9B107.4
C11—N3—Cu1110.8 (3)C9—C10—H10A109.5
C8—N3—Cu1102.9 (3)C9—C10—H10B109.5
C13—N4—Cu1168.0 (4)H10A—C10—H10B109.5
C14—N5—Cu1166.5 (5)C9—C10—H10C109.5
N1—C1—C2121.5 (6)H10A—C10—H10C109.5
N1—C1—H1119.3H10B—C10—H10C109.5
C2—C1—H1119.3N3—C11—C12116.5 (5)
C3—C2—C1118.5 (6)N3—C11—H11A108.2
C3—C2—H2120.8C12—C11—H11A108.2
C1—C2—H2120.8N3—C11—H11B108.2
C2—C3—C4121.7 (6)C12—C11—H11B108.2
C2—C3—H3119.2H11A—C11—H11B107.3
C4—C3—H3119.2C11—C12—H12A109.5
C3—C4—C5116.9 (6)C11—C12—H12B109.5
C3—C4—H4121.6H12A—C12—H12B109.5
C5—C4—H4121.6C11—C12—H12C109.5
N1—C5—C4122.0 (5)H12A—C12—H12C109.5
N1—C5—C6114.0 (5)H12B—C12—H12C109.5
C4—C5—C6124.0 (5)N4—C13—S1179.8 (5)
N2—C6—C5117.3 (4)N5—C14—S2178.8 (5)
 

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