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metal-organic compounds
In the title compound, [Cu(NCS)(C20H14N4)]SCN, the Cu atom is four-coordinated by a tridentate chelating 4′-(2-pyridyl)-2,2′:6′,2′′-terpyridine ligand and one isothiocyanate group in a square-planar coordination geometry. The sum of angles around the CuII center is 359.1°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031460/ac6136sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031460/ac6136Isup2.hkl |
CCDC reference: 262227
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.134
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level A ABSTM02_ALERT_3_A The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 Tmin and Tmax reported: 0.240 0.830 Tmin' and Tmax expected: 0.768 0.825 RR' = 0.310 Please check that your absorption correction is appropriate.
Author Response: The ratio is given by SADABS. |
PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.31
Author Response: The ratio is given by SADABS. |
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit P 2ybc PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7 N5 -CU1 -N2 -C10 -93.00 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 N5 -CU1 -N2 -C6 94.00 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 N2 -CU1 -N5 -C21 -9.00 2.00 1.555 1.555 1.555 1.555
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 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, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu(SCN)(C20H14N4)]SCN | F(000) = 996 |
Mr = 490.05 | Dx = 1.581 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ybc | Cell parameters from 2798 reflections |
a = 8.6898 (6) Å | θ = 2.7–27.2° |
b = 30.008 (2) Å | µ = 1.29 mm−1 |
c = 8.1262 (6) Å | T = 295 K |
β = 103.622 (1)° | Block, green |
V = 2059.4 (3) Å3 | 0.20 × 0.18 × 0.15 mm |
Z = 4 |
Data collection top
Bruker APEX area-dectector diffractometer | 4685 independent reflections |
Radiation source: fine-focus sealed tube | 3677 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→11 |
Tmin = 0.240, Tmax = 0.830 | k = −32→38 |
12864 measured reflections | l = −10→10 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0671P)2 + 1.0711P] where P = (Fo2 + 2Fc2)/3 |
4685 reflections | (Δ/σ)max = 0.001 |
280 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −0.58 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.52802 (5) | 0.66872 (1) | 0.57349 (5) | 0.0430 (2) | |
S1 | 0.72993 (14) | 0.80595 (3) | 0.4636 (2) | 0.0776 (4) | |
S2 | 0.32402 (14) | 0.64506 (3) | 0.2619 (1) | 0.0629 (3) | |
N1 | 0.3456 (3) | 0.6912 (1) | 0.6672 (3) | 0.0399 (6) | |
N2 | 0.4742 (3) | 0.6149 (1) | 0.6759 (3) | 0.0325 (5) | |
N3 | 0.7051 (3) | 0.6282 (1) | 0.5406 (3) | 0.0379 (6) | |
N4 | 0.1737 (3) | 0.4962 (1) | 0.8822 (3) | 0.0429 (6) | |
N5 | 0.5982 (4) | 0.7237 (1) | 0.4982 (4) | 0.0588 (8) | |
N6 | 0.2611 (4) | 0.5561 (1) | 0.3236 (5) | 0.0629 (8) | |
C1 | 0.2879 (4) | 0.7329 (1) | 0.6558 (4) | 0.0477 (8) | |
C2 | 0.1544 (4) | 0.7439 (1) | 0.7117 (5) | 0.0533 (9) | |
C3 | 0.0812 (4) | 0.7115 (1) | 0.7849 (5) | 0.0512 (8) | |
C4 | 0.1428 (4) | 0.6688 (1) | 0.8017 (4) | 0.0445 (7) | |
C5 | 0.2736 (4) | 0.6595 (1) | 0.7391 (4) | 0.0348 (6) | |
C6 | 0.3464 (3) | 0.6146 (1) | 0.7414 (4) | 0.0345 (6) | |
C7 | 0.2941 (3) | 0.5755 (1) | 0.7972 (4) | 0.0339 (6) | |
C8 | 0.3725 (3) | 0.5355 (1) | 0.7819 (3) | 0.0332 (6) | |
C9 | 0.5064 (3) | 0.5369 (1) | 0.7149 (4) | 0.0337 (6) | |
C10 | 0.5552 (3) | 0.5775 (1) | 0.6643 (4) | 0.0325 (6) | |
C11 | 0.6946 (3) | 0.5857 (1) | 0.5937 (4) | 0.0341 (6) | |
C12 | 0.8078 (4) | 0.5541 (1) | 0.5837 (4) | 0.0408 (7) | |
C13 | 0.9342 (4) | 0.5664 (1) | 0.5164 (4) | 0.0462 (8) | |
C14 | 0.9429 (4) | 0.6093 (1) | 0.4606 (4) | 0.0477 (8) | |
C15 | 0.8272 (4) | 0.6391 (1) | 0.4742 (4) | 0.0442 (7) | |
C16 | 0.3119 (3) | 0.4934 (1) | 0.8366 (3) | 0.0320 (6) | |
C17 | 0.3929 (4) | 0.4531 (1) | 0.8409 (4) | 0.0358 (6) | |
C18 | 0.3297 (4) | 0.4152 (1) | 0.8937 (4) | 0.0389 (7) | |
C19 | 0.1886 (4) | 0.4183 (1) | 0.9420 (4) | 0.0429 (7) | |
C20 | 0.1152 (4) | 0.4590 (1) | 0.9333 (5) | 0.0483 (8) | |
C21 | 0.6537 (4) | 0.7578 (1) | 0.4852 (5) | 0.0476 (8) | |
C22 | 0.2855 (4) | 0.5924 (1) | 0.2977 (4) | 0.0463 (8) | |
H1 | 0.3392 | 0.7550 | 0.6088 | 0.057* | |
H2 | 0.1148 | 0.7728 | 0.6999 | 0.064* | |
H3 | −0.0090 | 0.7182 | 0.8228 | 0.061* | |
H4 | 0.0967 | 0.6467 | 0.8544 | 0.053* | |
H7 | 0.2068 | 0.5756 | 0.8450 | 0.041* | |
H9 | 0.5618 | 0.5110 | 0.7044 | 0.040* | |
H12 | 0.7995 | 0.5252 | 0.6215 | 0.049* | |
H13 | 1.0122 | 0.5458 | 0.5091 | 0.055* | |
H14 | 1.0263 | 0.6180 | 0.4142 | 0.057* | |
H15 | 0.8336 | 0.6681 | 0.4359 | 0.053* | |
H17 | 0.4885 | 0.4520 | 0.8084 | 0.043* | |
H18 | 0.3815 | 0.3880 | 0.8968 | 0.047* | |
H19 | 0.1439 | 0.3933 | 0.9798 | 0.051* | |
H20 | 0.0192 | 0.4607 | 0.9648 | 0.058* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0444 (3) | 0.0281 (2) | 0.0615 (3) | −0.00130 (15) | 0.0228 (2) | 0.00608 (16) |
S1 | 0.0753 (7) | 0.0332 (5) | 0.135 (1) | −0.0133 (5) | 0.0459 (7) | −0.0018 (5) |
S2 | 0.0801 (7) | 0.0479 (5) | 0.0578 (6) | 0.0071 (5) | 0.0106 (5) | 0.0080 (4) |
N1 | 0.045 (2) | 0.028 (1) | 0.047 (2) | 0.001 (1) | 0.012 (1) | −0.001 (1) |
N2 | 0.033 (1) | 0.028 (1) | 0.038 (1) | −0.002 (1) | 0.010 (1) | 0.001 (1) |
N3 | 0.034 (1) | 0.037 (1) | 0.045 (1) | −0.005 (1) | 0.013 (1) | 0.001 (1) |
N4 | 0.042 (2) | 0.031 (1) | 0.063 (2) | 0.000 (1) | 0.026 (1) | 0.001 (1) |
N5 | 0.070 (2) | 0.034 (2) | 0.081 (2) | −0.008 (1) | 0.034 (2) | 0.006 (1) |
N6 | 0.055 (2) | 0.048 (2) | 0.085 (2) | −0.002 (2) | 0.015 (2) | −0.010 (2) |
C1 | 0.056 (2) | 0.029 (2) | 0.061 (2) | 0.001 (1) | 0.018 (2) | 0.000 (1) |
C2 | 0.060 (2) | 0.030 (2) | 0.071 (2) | 0.008 (2) | 0.018 (2) | −0.005 (2) |
C3 | 0.051 (2) | 0.042 (2) | 0.065 (2) | 0.007 (2) | 0.024 (2) | −0.010 (2) |
C4 | 0.049 (2) | 0.036 (2) | 0.052 (2) | 0.000 (1) | 0.017 (2) | −0.004 (1) |
C5 | 0.037 (2) | 0.029 (1) | 0.038 (2) | 0.001 (1) | 0.008 (1) | −0.001 (1) |
C6 | 0.035 (2) | 0.031 (1) | 0.039 (2) | 0.000 (1) | 0.010 (1) | −0.001 (1) |
C7 | 0.033 (2) | 0.031 (1) | 0.040 (2) | −0.001 (1) | 0.012 (1) | 0.000 (1) |
C8 | 0.034 (2) | 0.032 (1) | 0.033 (1) | −0.003 (1) | 0.006 (1) | 0.000 (1) |
C9 | 0.035 (2) | 0.028 (1) | 0.039 (2) | 0.001 (1) | 0.010 (1) | 0.001 (1) |
C10 | 0.032 (2) | 0.033 (1) | 0.032 (2) | −0.001 (1) | 0.007 (1) | −0.002 (1) |
C11 | 0.032 (2) | 0.034 (2) | 0.036 (2) | −0.003 (1) | 0.008 (1) | −0.003 (1) |
C12 | 0.039 (2) | 0.039 (2) | 0.046 (2) | 0.002 (1) | 0.011 (1) | −0.001 (1) |
C13 | 0.034 (2) | 0.053 (2) | 0.052 (2) | 0.003 (1) | 0.012 (2) | −0.007 (2) |
C14 | 0.038 (2) | 0.056 (2) | 0.054 (2) | −0.008 (2) | 0.018 (2) | −0.009 (2) |
C15 | 0.043 (2) | 0.041 (2) | 0.050 (2) | −0.010 (1) | 0.015 (2) | −0.001 (1) |
C16 | 0.035 (2) | 0.027 (1) | 0.035 (2) | 0.000 (1) | 0.009 (1) | 0.000 (1) |
C17 | 0.034 (2) | 0.034 (2) | 0.039 (2) | 0.000 (1) | 0.009 (1) | −0.001 (1) |
C18 | 0.045 (2) | 0.025 (1) | 0.047 (2) | 0.003 (1) | 0.011 (1) | 0.000 (1) |
C19 | 0.051 (2) | 0.030 (2) | 0.053 (2) | −0.006 (1) | 0.020 (2) | 0.002 (1) |
C20 | 0.048 (2) | 0.039 (2) | 0.066 (2) | −0.003 (1) | 0.030 (2) | 0.000 (2) |
C21 | 0.046 (2) | 0.037 (2) | 0.066 (2) | 0.003 (1) | 0.024 (1) | 0.001 (2) |
C22 | 0.036 (2) | 0.053 (2) | 0.049 (2) | 0.010 (2) | 0.010 (1) | −0.006 (2) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.029 (3) | C8—C16 | 1.479 (4) |
Cu1—N2 | 1.924 (2) | C9—C10 | 1.383 (4) |
Cu1—N3 | 2.029 (3) | C10—C11 | 1.477 (4) |
Cu1—N5 | 1.909 (3) | C11—C12 | 1.381 (4) |
Cu1—S2 | 2.819 (1) | C12—C13 | 1.387 (4) |
S1—C21 | 1.617 (3) | C13—C14 | 1.373 (5) |
S2—C22 | 1.655 (4) | C14—C15 | 1.370 (5) |
N1—C1 | 1.342 (4) | C16—C17 | 1.393 (4) |
N1—C5 | 1.345 (4) | C17—C18 | 1.376 (4) |
N2—C10 | 1.340 (4) | C18—C19 | 1.376 (4) |
N2—C6 | 1.340 (4) | C19—C20 | 1.372 (4) |
N3—C15 | 1.340 (4) | C1—H1 | 0.93 |
N3—C11 | 1.356 (4) | C2—H2 | 0.93 |
N4—C20 | 1.333 (4) | C3—H3 | 0.93 |
N4—C16 | 1.341 (4) | C4—H4 | 0.93 |
N5—C21 | 1.146 (4) | C7—H7 | 0.93 |
N6—C22 | 1.140 (4) | C9—H9 | 0.93 |
C1—C2 | 1.382 (5) | C12—H12 | 0.93 |
C2—C3 | 1.372 (5) | C13—H13 | 0.93 |
C3—C4 | 1.383 (4) | C14—H14 | 0.93 |
C4—C5 | 1.379 (4) | C15—H15 | 0.93 |
C5—C6 | 1.487 (4) | C17—H17 | 0.93 |
C6—C7 | 1.374 (4) | C18—H18 | 0.93 |
C7—C8 | 1.399 (4) | C19—H19 | 0.93 |
C8—C9 | 1.397 (4) | C20—H20 | 0.93 |
N1—Cu1—N2 | 80.0 (1) | C15—C14—C13 | 119.2 (3) |
N1—Cu1—N3 | 158.9 (1) | N3—C15—C14 | 122.5 (3) |
N1—Cu1—N5 | 99.7 (1) | N4—C16—C17 | 121.9 (3) |
N2—Cu1—N3 | 79.8 (1) | N4—C16—C8 | 115.8 (2) |
N2—Cu1—N5 | 173.0 (1) | C17—C16—C8 | 122.4 (3) |
N3—Cu1—N5 | 99.6 (1) | C18—C17—C16 | 119.2 (3) |
C1—N1—C5 | 119.0 (3) | C17—C18—C19 | 118.8 (3) |
C1—N1—Cu1 | 126.6 (2) | C20—C19—C18 | 118.7 (3) |
C5—N1—Cu1 | 114.3 (2) | N4—C20—C19 | 123.7 (3) |
C10—N2—C6 | 121.3 (2) | N5—C21—S1 | 179.0 (4) |
C10—N2—Cu1 | 119.2 (2) | N6—C22—S2 | 179.1 (4) |
C6—N2—Cu1 | 119.1 (2) | N1—C1—H1 | 119.0 |
C15—N3—C11 | 118.6 (3) | C2—C1—H1 | 119.0 |
C15—N3—Cu1 | 127.1 (2) | C3—C2—H2 | 120.6 |
C11—N3—Cu1 | 114.4 (2) | C1—C2—H2 | 120.6 |
C20—N4—C16 | 117.7 (3) | C2—C3—H3 | 120.3 |
C21—N5—Cu1 | 166.9 (3) | C4—C3—H3 | 120.3 |
N1—C1—C2 | 122.0 (3) | C5—C4—H4 | 120.5 |
C3—C2—C1 | 118.9 (3) | C3—C4—H4 | 120.5 |
C2—C3—C4 | 119.5 (3) | C6—C7—H7 | 120.1 |
C5—C4—C3 | 118.9 (3) | C8—C7—H7 | 120.1 |
N1—C5—C4 | 121.7 (3) | C10—C9—H9 | 120.5 |
N1—C5—C6 | 114.0 (3) | C8—C9—H9 | 120.5 |
C4—C5—C6 | 124.2 (3) | C11—C12—H12 | 120.6 |
N2—C6—C7 | 120.5 (3) | C13—C12—H12 | 120.6 |
N2—C6—C5 | 112.2 (2) | C14—C13—H13 | 120.3 |
C7—C6—C5 | 127.3 (3) | C12—C13—H13 | 120.3 |
C6—C7—C8 | 119.8 (3) | C15—C14—H14 | 120.4 |
C9—C8—C7 | 118.5 (3) | C13—C14—H14 | 120.4 |
C9—C8—C16 | 122.1 (3) | N3—C15—H15 | 118.7 |
C7—C8—C16 | 119.4 (2) | C14—C15—H15 | 118.7 |
C10—C9—C8 | 119.0 (3) | C18—C17—H17 | 120.4 |
N2—C10—C9 | 120.9 (3) | C16—C17—H17 | 120.4 |
N2—C10—C11 | 112.4 (2) | C17—C18—H18 | 120.6 |
C9—C10—C11 | 126.7 (3) | C19—C18—H18 | 120.6 |
N3—C11—C12 | 121.5 (3) | C20—C19—H19 | 120.7 |
N3—C11—C10 | 113.7 (2) | C18—C19—H19 | 120.7 |
C12—C11—C10 | 124.8 (3) | N4—C20—H20 | 118.1 |
C11—C12—C13 | 118.9 (3) | C19—C20—H20 | 118.1 |
C14—C13—C12 | 119.3 (3) | ||
N5—Cu1—N1—C1 | 6.6 (3) | N2—C6—C7—C8 | −1.5 (4) |
N2—Cu1—N1—C1 | 179.5 (3) | C5—C6—C7—C8 | 176.6 (3) |
N3—Cu1—N1—C1 | 163.1 (3) | C6—C7—C8—C9 | 2.2 (4) |
N5—Cu1—N1—C5 | −177.1 (2) | C6—C7—C8—C16 | −177.8 (3) |
N2—Cu1—N1—C5 | −4.2 (2) | C7—C8—C9—C10 | −0.8 (4) |
N3—Cu1—N1—C5 | −20.7 (4) | C16—C8—C9—C10 | 179.2 (3) |
N5—Cu1—N2—C10 | −93 (1) | C6—N2—C10—C9 | 2.1 (4) |
N3—Cu1—N2—C10 | −7.1 (2) | Cu1—N2—C10—C9 | −170.8 (2) |
N1—Cu1—N2—C10 | 178.9 (2) | C6—N2—C10—C11 | −178.1 (3) |
N5—Cu1—N2—C6 | 94 (1) | Cu1—N2—C10—C11 | 9.0 (3) |
N3—Cu1—N2—C6 | 179.9 (2) | C8—C9—C10—N2 | −1.3 (4) |
N1—Cu1—N2—C6 | 5.8 (2) | C8—C9—C10—C11 | 178.9 (3) |
N5—Cu1—N3—C15 | −3.5 (3) | C15—N3—C11—C12 | 1.3 (4) |
N2—Cu1—N3—C15 | −176.4 (3) | Cu1—N3—C11—C12 | −178.5 (2) |
N1—Cu1—N3—C15 | −160.0 (3) | C15—N3—C11—C10 | −180.0 (3) |
N5—Cu1—N3—C11 | 176.3 (2) | Cu1—N3—C11—C10 | 0.2 (3) |
N2—Cu1—N3—C11 | 3.4 (2) | N2—C10—C11—N3 | −5.6 (4) |
N1—Cu1—N3—C11 | 19.8 (4) | C9—C10—C11—N3 | 174.1 (3) |
N2—Cu1—N5—C21 | −9 (2) | N2—C10—C11—C12 | 173.1 (3) |
N3—Cu1—N5—C21 | −93 (1) | C9—C10—C11—C12 | −7.2 (5) |
N1—Cu1—N5—C21 | 79 (1) | N3—C11—C12—C13 | −0.5 (5) |
C5—N1—C1—C2 | −1.7 (5) | C10—C11—C12—C13 | −179.1 (3) |
Cu1—N1—C1—C2 | 174.4 (3) | C11—C12—C13—C14 | −0.4 (5) |
N1—C1—C2—C3 | 1.7 (6) | C12—C13—C14—C15 | 0.6 (5) |
C1—C2—C3—C4 | 0.3 (6) | C11—N3—C15—C14 | −1.1 (5) |
C2—C3—C4—C5 | −2.2 (5) | Cu1—N3—C15—C14 | 178.7 (2) |
C1—N1—C5—C4 | −0.3 (5) | C13—C14—C15—N3 | 0.2 (5) |
Cu1—N1—C5—C4 | −176.9 (2) | C20—N4—C16—C17 | 0.3 (4) |
C1—N1—C5—C6 | 178.9 (3) | C20—N4—C16—C8 | −179.6 (3) |
Cu1—N1—C5—C6 | 2.3 (3) | C9—C8—C16—N4 | −173.5 (3) |
C3—C4—C5—N1 | 2.2 (5) | C7—C8—C16—N4 | 6.5 (4) |
C3—C4—C5—C6 | −176.9 (3) | C9—C8—C16—C17 | 6.6 (4) |
C10—N2—C6—C7 | −0.6 (4) | C7—C8—C16—C17 | −173.4 (3) |
Cu1—N2—C6—C7 | 172.3 (2) | N4—C16—C17—C18 | −0.1 (4) |
C10—N2—C6—C5 | −179.0 (2) | C8—C16—C17—C18 | 179.8 (3) |
Cu1—N2—C6—C5 | −6.1 (3) | C16—C17—C18—C19 | −0.5 (5) |
N1—C5—C6—N2 | 2.2 (4) | C17—C18—C19—C20 | 0.9 (5) |
C4—C5—C6—N2 | −178.7 (3) | C16—N4—C20—C19 | 0.2 (5) |
N1—C5—C6—C7 | −176.0 (3) | C18—C19—C20—N4 | −0.8 (6) |
C4—C5—C6—C7 | 3.1 (5) |
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