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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
CCDC reference: 605020
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
Crystal data top
[Cu(C12H19N3)(NCS)2] | Dx = 1.433 Mg m−3 |
Mr = 385.00 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from 3609 reflections |
Hall symbol: P 4w | θ = 2.4–25.1° |
a = 7.294 (1) Å | µ = 1.46 mm−1 |
c = 33.549 (3) Å | T = 298 K |
V = 1784.9 (4) Å3 | Block, blue |
Z = 4 | 0.35 × 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 tube | 2778 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scan | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.629, Tmax = 0.868 | k = −9→9 |
15425 measured reflections | l = −43→43 |
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)] = 0.044 | H-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 reflections | Δρmax = 0.33 e Å−3 |
201 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983); 1995 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.92314 (7) | 0.04551 (6) | 0.796394 (14) | 0.07533 (17) | |
S1 | 0.6294 (2) | 0.57390 (17) | 0.75221 (4) | 0.1025 (4) | |
S2 | 1.2512 (3) | 0.4069 (3) | 0.89374 (6) | 0.1442 (7) | |
N1 | 0.7381 (5) | −0.0536 (5) | 0.83716 (10) | 0.0790 (9) | |
N2 | 1.0267 (6) | −0.1971 (5) | 0.80643 (12) | 0.0894 (11) | |
N3 | 1.0962 (4) | 0.0317 (5) | 0.74660 (13) | 0.0824 (10) | |
N4 | 0.7747 (6) | 0.2505 (6) | 0.78057 (12) | 0.1056 (15) | |
N5 | 1.1000 (8) | 0.1917 (8) | 0.83668 (17) | 0.1261 (17) | |
C1 | 0.5989 (7) | 0.0316 (8) | 0.85374 (14) | 0.0999 (14) | |
H1 | 0.5713 | 0.1507 | 0.8458 | 0.120* | |
C2 | 0.4911 (9) | −0.0529 (10) | 0.8831 (2) | 0.125 (2) | |
H2 | 0.3930 | 0.0087 | 0.8947 | 0.149* | |
C3 | 0.5323 (11) | −0.2226 (12) | 0.89397 (18) | 0.133 (2) | |
H3 | 0.4635 | −0.2788 | 0.9139 | 0.159* | |
C4 | 0.6749 (10) | −0.3183 (9) | 0.87647 (19) | 0.123 (2) | |
H4 | 0.7013 | −0.4386 | 0.8836 | 0.148* | |
C5 | 0.7764 (7) | −0.2265 (7) | 0.84790 (14) | 0.0871 (13) | |
C6 | 0.9371 (9) | −0.3015 (7) | 0.82880 (17) | 0.1013 (16) | |
H6 | 0.9727 | −0.4225 | 0.8329 | 0.122* | |
C7 | 1.1875 (9) | −0.2489 (8) | 0.7836 (2) | 0.122 (2) | |
H7A | 1.1567 | −0.3442 | 0.7646 | 0.146* | |
H7B | 1.2824 | −0.2951 | 0.8012 | 0.146* | |
C8 | 1.2552 (7) | −0.0763 (9) | 0.7617 (2) | 0.1126 (18) | |
H8A | 1.3271 | −0.0014 | 0.7798 | 0.135* | |
H8B | 1.3331 | −0.1116 | 0.7396 | 0.135* | |
C9 | 1.0083 (9) | −0.0708 (8) | 0.71385 (19) | 0.1080 (17) | |
H9A | 1.0939 | −0.0780 | 0.6918 | 0.130* | |
H9B | 0.9854 | −0.1951 | 0.7229 | 0.130* | |
C10 | 0.8348 (12) | 0.0061 (10) | 0.6989 (2) | 0.148 (3) | |
H10A | 0.7490 | 0.0162 | 0.7205 | 0.222* | |
H10B | 0.7853 | −0.0731 | 0.6788 | 0.222* | |
H10C | 0.8569 | 0.1253 | 0.6878 | 0.222* | |
C11 | 1.1598 (7) | 0.2181 (7) | 0.73486 (17) | 0.0951 (14) | |
H11A | 1.2136 | 0.2761 | 0.7581 | 0.114* | |
H11B | 1.0533 | 0.2898 | 0.7273 | 0.114* | |
C12 | 1.2982 (9) | 0.2277 (10) | 0.7009 (2) | 0.139 (2) | |
H12A | 1.4132 | 0.1777 | 0.7097 | 0.208* | |
H12B | 1.3151 | 0.3532 | 0.6931 | 0.208* | |
H12C | 1.2536 | 0.1583 | 0.6786 | 0.208* | |
C13 | 0.7145 (6) | 0.3850 (7) | 0.76873 (12) | 0.0775 (11) | |
C14 | 1.1606 (6) | 0.2808 (6) | 0.86033 (15) | 0.0781 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0768 (3) | 0.0713 (3) | 0.0779 (3) | 0.0230 (2) | −0.0049 (3) | 0.0022 (3) |
S1 | 0.1163 (9) | 0.0879 (8) | 0.1032 (9) | 0.0377 (7) | −0.0080 (8) | 0.0079 (7) |
S2 | 0.1579 (15) | 0.1175 (12) | 0.1573 (16) | −0.0130 (11) | −0.0253 (13) | −0.0358 (11) |
N1 | 0.091 (2) | 0.083 (2) | 0.0633 (19) | 0.011 (2) | −0.0085 (18) | 0.0003 (17) |
N2 | 0.104 (3) | 0.075 (2) | 0.089 (3) | 0.034 (2) | −0.009 (2) | −0.006 (2) |
N3 | 0.069 (2) | 0.086 (2) | 0.092 (3) | 0.0060 (18) | −0.0052 (18) | −0.011 (2) |
N4 | 0.099 (3) | 0.101 (3) | 0.117 (4) | 0.047 (2) | 0.000 (2) | 0.027 (2) |
N5 | 0.138 (4) | 0.117 (4) | 0.124 (4) | 0.010 (3) | −0.042 (3) | −0.027 (3) |
C1 | 0.098 (3) | 0.121 (4) | 0.081 (3) | 0.021 (3) | 0.010 (3) | 0.010 (3) |
C2 | 0.103 (4) | 0.158 (6) | 0.112 (4) | 0.014 (4) | 0.009 (3) | 0.008 (4) |
C3 | 0.140 (5) | 0.172 (7) | 0.086 (4) | −0.013 (5) | 0.016 (4) | 0.025 (4) |
C4 | 0.162 (6) | 0.106 (4) | 0.103 (4) | −0.005 (4) | −0.010 (4) | 0.033 (4) |
C5 | 0.107 (3) | 0.081 (3) | 0.074 (3) | 0.010 (3) | −0.010 (2) | 0.006 (2) |
C6 | 0.138 (5) | 0.070 (3) | 0.096 (3) | 0.029 (3) | −0.023 (3) | 0.008 (3) |
C7 | 0.114 (4) | 0.104 (4) | 0.148 (6) | 0.056 (3) | 0.005 (4) | −0.001 (4) |
C8 | 0.077 (3) | 0.121 (4) | 0.140 (5) | 0.022 (3) | 0.003 (3) | −0.025 (4) |
C9 | 0.101 (3) | 0.122 (4) | 0.101 (4) | −0.011 (3) | 0.013 (3) | −0.025 (3) |
C10 | 0.170 (7) | 0.142 (5) | 0.132 (6) | 0.001 (5) | −0.069 (5) | −0.014 (4) |
C11 | 0.094 (3) | 0.083 (3) | 0.109 (4) | −0.008 (3) | 0.013 (3) | −0.003 (3) |
C12 | 0.121 (5) | 0.131 (5) | 0.164 (6) | −0.020 (4) | 0.044 (4) | 0.003 (5) |
C13 | 0.069 (2) | 0.097 (3) | 0.066 (2) | 0.022 (2) | 0.0107 (19) | −0.001 (2) |
C14 | 0.085 (3) | 0.065 (2) | 0.083 (3) | 0.005 (2) | 0.000 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
Cu1—N4 | 1.921 (4) | C4—C5 | 1.384 (8) |
Cu1—N2 | 1.954 (3) | C4—H4 | 0.93 |
Cu1—N1 | 2.053 (4) | C5—C6 | 1.444 (8) |
Cu1—N3 | 2.096 (4) | C6—H6 | 0.93 |
Cu1—N5 | 2.151 (5) | C7—C8 | 1.540 (9) |
S1—C13 | 1.610 (5) | C7—H7A | 0.97 |
S2—C14 | 1.594 (5) | C7—H7B | 0.97 |
N1—C1 | 1.314 (7) | C8—H8A | 0.97 |
N1—C5 | 1.341 (6) | C8—H8B | 0.97 |
N2—C6 | 1.253 (7) | C9—C10 | 1.472 (9) |
N2—C7 | 1.450 (7) | C9—H9A | 0.97 |
N3—C9 | 1.476 (7) | C9—H9B | 0.97 |
N3—C11 | 1.489 (6) | C10—H10A | 0.96 |
N3—C8 | 1.491 (7) | C10—H10B | 0.96 |
N4—C13 | 1.146 (5) | C10—H10C | 0.96 |
N5—C14 | 1.117 (6) | C11—C12 | 1.523 (8) |
C1—C2 | 1.403 (8) | C11—H11A | 0.97 |
C1—H1 | 0.93 | C11—H11B | 0.97 |
C2—C3 | 1.325 (9) | C12—H12A | 0.96 |
C2—H2 | 0.93 | C12—H12B | 0.96 |
C3—C4 | 1.383 (10) | C12—H12C | 0.96 |
C3—H3 | 0.93 | | |
| | | |
N4—Cu1—N2 | 166.1 (2) | N2—C6—H6 | 121.3 |
N4—Cu1—N1 | 95.02 (18) | C5—C6—H6 | 121.3 |
N2—Cu1—N1 | 79.66 (18) | N2—C7—C8 | 107.3 (4) |
N4—Cu1—N3 | 99.01 (17) | N2—C7—H7A | 110.3 |
N2—Cu1—N3 | 82.00 (17) | C8—C7—H7A | 110.3 |
N1—Cu1—N3 | 155.49 (15) | N2—C7—H7B | 110.3 |
N4—Cu1—N5 | 97.2 (2) | C8—C7—H7B | 110.3 |
N2—Cu1—N5 | 96.25 (19) | H7A—C7—H7B | 108.5 |
N1—Cu1—N5 | 98.6 (2) | N3—C8—C7 | 110.2 (4) |
N3—Cu1—N5 | 99.4 (2) | N3—C8—H8A | 109.6 |
C1—N1—C5 | 119.5 (5) | C7—C8—H8A | 109.6 |
C1—N1—Cu1 | 128.5 (3) | N3—C8—H8B | 109.6 |
C5—N1—Cu1 | 111.9 (3) | C7—C8—H8B | 109.6 |
C6—N2—C7 | 125.4 (4) | H8A—C8—H8B | 108.1 |
C6—N2—Cu1 | 116.9 (4) | C10—C9—N3 | 115.7 (5) |
C7—N2—Cu1 | 117.3 (4) | C10—C9—H9A | 108.4 |
C9—N3—C11 | 113.6 (4) | N3—C9—H9A | 108.4 |
C9—N3—C8 | 108.9 (4) | C10—C9—H9B | 108.4 |
C11—N3—C8 | 109.3 (4) | N3—C9—H9B | 108.4 |
C9—N3—Cu1 | 110.8 (3) | H9A—C9—H9B | 107.4 |
C11—N3—Cu1 | 110.8 (3) | C9—C10—H10A | 109.5 |
C8—N3—Cu1 | 102.9 (3) | C9—C10—H10B | 109.5 |
C13—N4—Cu1 | 168.0 (4) | H10A—C10—H10B | 109.5 |
C14—N5—Cu1 | 166.5 (5) | C9—C10—H10C | 109.5 |
N1—C1—C2 | 121.5 (6) | H10A—C10—H10C | 109.5 |
N1—C1—H1 | 119.3 | H10B—C10—H10C | 109.5 |
C2—C1—H1 | 119.3 | N3—C11—C12 | 116.5 (5) |
C3—C2—C1 | 118.5 (6) | N3—C11—H11A | 108.2 |
C3—C2—H2 | 120.8 | C12—C11—H11A | 108.2 |
C1—C2—H2 | 120.8 | N3—C11—H11B | 108.2 |
C2—C3—C4 | 121.7 (6) | C12—C11—H11B | 108.2 |
C2—C3—H3 | 119.2 | H11A—C11—H11B | 107.3 |
C4—C3—H3 | 119.2 | C11—C12—H12A | 109.5 |
C3—C4—C5 | 116.9 (6) | C11—C12—H12B | 109.5 |
C3—C4—H4 | 121.6 | H12A—C12—H12B | 109.5 |
C5—C4—H4 | 121.6 | C11—C12—H12C | 109.5 |
N1—C5—C4 | 122.0 (5) | H12A—C12—H12C | 109.5 |
N1—C5—C6 | 114.0 (5) | H12B—C12—H12C | 109.5 |
C4—C5—C6 | 124.0 (5) | N4—C13—S1 | 179.8 (5) |
N2—C6—C5 | 117.3 (4) | N5—C14—S2 | 178.8 (5) |
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