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The title compound, [Cu(C14H15N2O)(NCS)], is a mononuclear copper(II) complex, with two molecules in the asymmetric unit. The CuII ion is coordinated by one O and two N atoms of a Schiff base ligand, and by one N atom of a thio­cyanate anion, forming a square-planar geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021544/at2040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021544/at2040Isup2.hkl
Contains datablock I

CCDC reference: 613568

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.124
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.02 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C30 PLAT410_ALERT_2_C Short Intra H...H Contact H9 .. H11 .. 1.99 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

{1-[2-(Methylamino)ethyliminomethyl]naphthalen-2-olato}thiocyanatocopper(II) top
Crystal data top
[Cu(C14H15N2O)(NCS)]F(000) = 1432
Mr = 348.90Dx = 1.548 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4973 reflections
a = 10.168 (1) Åθ = 2.4–25.0°
b = 13.237 (1) ŵ = 1.60 mm1
c = 22.301 (2) ÅT = 298 K
β = 93.679 (1)°Block, blue
V = 2995.4 (5) Å30.22 × 0.18 × 0.17 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
6734 independent reflections
Radiation source: fine-focus sealed tube5081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.720, Tmax = 0.773k = 1616
22106 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0641P)2 + 0.9166P]
where P = (Fo2 + 2Fc2)/3
6734 reflections(Δ/σ)max < 0.001
387 parametersΔρmax = 0.80 e Å3
2 restraintsΔρmin = 0.26 e Å3
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
Cu10.63072 (4)0.43441 (3)0.478972 (17)0.04094 (12)
Cu20.30265 (4)0.29436 (3)0.235880 (18)0.04505 (13)
S10.34501 (10)0.49413 (8)0.30872 (4)0.0622 (3)
S20.25778 (15)0.47976 (8)0.05693 (5)0.0809 (4)
O10.7035 (2)0.56515 (15)0.46642 (10)0.0410 (5)
O20.4642 (2)0.2456 (2)0.20777 (11)0.0564 (6)
N10.7628 (2)0.40288 (17)0.54040 (11)0.0371 (5)
N20.5323 (3)0.3143 (2)0.51184 (15)0.0553 (8)
N30.4994 (3)0.4544 (2)0.41285 (15)0.0560 (7)
N40.3210 (3)0.2073 (2)0.30509 (13)0.0479 (7)
N50.1133 (3)0.3126 (2)0.26143 (13)0.0504 (7)
N60.2801 (3)0.3869 (2)0.16825 (13)0.0521 (7)
C10.8854 (3)0.5597 (2)0.54105 (14)0.0338 (6)
C20.8068 (3)0.6062 (2)0.49474 (14)0.0369 (7)
C30.8383 (3)0.7066 (2)0.47768 (15)0.0462 (8)
H30.78640.73800.44730.055*
C40.9416 (3)0.7577 (2)0.50451 (16)0.0497 (8)
H40.95810.82360.49250.060*
C51.0245 (3)0.7133 (2)0.55014 (15)0.0428 (7)
C61.1347 (4)0.7661 (3)0.57654 (17)0.0532 (9)
H61.15100.83200.56450.064*
C71.2164 (4)0.7221 (3)0.61892 (18)0.0597 (10)
H71.28910.75730.63550.072*
C81.1919 (3)0.6240 (3)0.63782 (17)0.0565 (9)
H81.24810.59420.66730.068*
C91.0861 (3)0.5711 (3)0.61343 (16)0.0482 (8)
H91.07150.50570.62660.058*
C100.9987 (3)0.6134 (2)0.56877 (14)0.0376 (7)
C110.8565 (3)0.4606 (2)0.56156 (14)0.0377 (7)
H110.91050.43520.59330.045*
C120.7443 (3)0.3039 (2)0.56816 (17)0.0490 (8)
H12A0.78550.30280.60860.059*
H12B0.78380.25140.54490.059*
C130.5988 (3)0.2867 (3)0.56962 (17)0.0528 (9)
H13A0.58210.21620.57820.063*
H13B0.56430.32710.60130.063*
C140.5051 (4)0.2298 (3)0.4705 (2)0.0693 (11)
H14A0.58580.19510.46390.104*
H14B0.46700.25500.43290.104*
H14C0.44460.18390.48760.104*
C150.4354 (3)0.4690 (2)0.36934 (15)0.0433 (7)
C160.5321 (3)0.1321 (2)0.28819 (14)0.0395 (7)
C170.5479 (3)0.1825 (2)0.23311 (15)0.0457 (8)
C180.6649 (4)0.1641 (3)0.20299 (17)0.0583 (9)
H180.67660.19650.16670.070*
C190.7594 (4)0.1005 (3)0.22589 (18)0.0594 (10)
H190.83360.08960.20440.071*
C200.7497 (3)0.0500 (2)0.28135 (17)0.0499 (8)
C210.8508 (4)0.0146 (3)0.3056 (2)0.0640 (11)
H210.92430.02590.28370.077*
C220.8437 (4)0.0600 (3)0.3589 (2)0.0673 (11)
H220.91110.10230.37380.081*
C230.7335 (4)0.0430 (3)0.39215 (19)0.0609 (10)
H230.72870.07280.42970.073*
C240.6326 (3)0.0176 (2)0.36955 (15)0.0482 (8)
H240.55970.02720.39210.058*
C250.6361 (3)0.0654 (2)0.31338 (15)0.0422 (7)
C260.4152 (3)0.1450 (2)0.31917 (14)0.0435 (7)
H260.40600.10470.35280.052*
C270.2078 (4)0.2126 (3)0.34271 (19)0.0666 (11)
H27A0.21810.26870.37060.080*
H27B0.20060.15070.36550.080*
C280.0892 (4)0.2271 (3)0.30180 (18)0.0613 (10)
H28A0.07110.16630.27850.074*
H28B0.01350.24140.32480.074*
C290.0054 (4)0.3225 (4)0.2155 (2)0.0872 (15)
H29A0.00270.26120.19250.131*
H29B0.02320.37780.18930.131*
H29C0.07530.33510.23430.131*
C300.2723 (3)0.4260 (2)0.12231 (15)0.0449 (7)
H50.127 (4)0.3727 (16)0.2794 (17)0.080*
H20.451 (2)0.338 (3)0.5188 (19)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0397 (2)0.0383 (2)0.0439 (2)0.00154 (15)0.00387 (17)0.00144 (16)
Cu20.0452 (2)0.0487 (2)0.0411 (2)0.00170 (17)0.00176 (18)0.01097 (17)
S10.0766 (6)0.0666 (6)0.0411 (5)0.0109 (5)0.0131 (5)0.0068 (4)
S20.1527 (12)0.0488 (5)0.0410 (5)0.0004 (6)0.0035 (6)0.0100 (4)
O10.0412 (11)0.0382 (11)0.0429 (12)0.0021 (9)0.0030 (9)0.0057 (9)
O20.0510 (14)0.0739 (16)0.0454 (14)0.0076 (12)0.0106 (11)0.0202 (13)
N10.0412 (13)0.0296 (12)0.0401 (14)0.0033 (10)0.0001 (11)0.0027 (10)
N20.0501 (17)0.0460 (16)0.069 (2)0.0079 (13)0.0002 (16)0.0038 (15)
N30.0510 (17)0.0570 (18)0.0582 (19)0.0036 (14)0.0100 (15)0.0042 (15)
N40.0449 (15)0.0534 (16)0.0465 (16)0.0096 (12)0.0112 (13)0.0133 (13)
N50.0517 (17)0.0511 (16)0.0482 (17)0.0124 (13)0.0013 (14)0.0047 (13)
N60.0658 (19)0.0478 (16)0.0417 (16)0.0006 (14)0.0047 (14)0.0097 (13)
C10.0322 (14)0.0297 (14)0.0399 (16)0.0004 (11)0.0066 (12)0.0020 (12)
C20.0371 (15)0.0351 (15)0.0394 (17)0.0019 (12)0.0085 (13)0.0005 (13)
C30.0521 (19)0.0398 (17)0.047 (2)0.0020 (14)0.0075 (16)0.0124 (14)
C40.061 (2)0.0341 (16)0.055 (2)0.0050 (15)0.0151 (17)0.0068 (15)
C50.0457 (17)0.0401 (16)0.0441 (19)0.0074 (13)0.0141 (15)0.0074 (14)
C60.057 (2)0.0459 (19)0.058 (2)0.0179 (16)0.0147 (18)0.0082 (17)
C70.0458 (19)0.067 (2)0.067 (3)0.0170 (17)0.0065 (18)0.019 (2)
C80.0451 (19)0.061 (2)0.062 (2)0.0018 (16)0.0042 (17)0.0100 (19)
C90.0410 (17)0.0447 (18)0.058 (2)0.0003 (13)0.0012 (16)0.0020 (15)
C100.0340 (15)0.0372 (15)0.0427 (17)0.0012 (12)0.0108 (13)0.0062 (13)
C110.0375 (15)0.0349 (15)0.0404 (17)0.0033 (12)0.0003 (13)0.0014 (13)
C120.054 (2)0.0371 (17)0.055 (2)0.0052 (14)0.0051 (16)0.0111 (15)
C130.059 (2)0.0406 (18)0.059 (2)0.0040 (15)0.0047 (18)0.0082 (16)
C140.080 (3)0.052 (2)0.075 (3)0.017 (2)0.006 (2)0.013 (2)
C150.0427 (17)0.0426 (16)0.0445 (19)0.0075 (13)0.0023 (15)0.0008 (14)
C160.0406 (16)0.0359 (15)0.0419 (18)0.0027 (12)0.0013 (14)0.0024 (13)
C170.0432 (17)0.0484 (18)0.0460 (19)0.0032 (14)0.0058 (15)0.0009 (15)
C180.059 (2)0.065 (2)0.053 (2)0.0010 (18)0.0172 (18)0.0073 (18)
C190.048 (2)0.061 (2)0.072 (3)0.0024 (17)0.0216 (19)0.007 (2)
C200.0429 (18)0.0419 (18)0.065 (2)0.0014 (14)0.0052 (16)0.0082 (16)
C210.048 (2)0.057 (2)0.087 (3)0.0080 (17)0.004 (2)0.011 (2)
C220.061 (2)0.058 (2)0.082 (3)0.0178 (18)0.007 (2)0.001 (2)
C230.074 (3)0.046 (2)0.061 (2)0.0108 (18)0.012 (2)0.0015 (17)
C240.0547 (19)0.0419 (17)0.047 (2)0.0062 (14)0.0025 (16)0.0051 (15)
C250.0424 (17)0.0350 (15)0.0490 (19)0.0017 (12)0.0004 (14)0.0084 (14)
C260.0508 (18)0.0431 (17)0.0370 (17)0.0055 (14)0.0061 (14)0.0079 (14)
C270.063 (2)0.076 (3)0.063 (3)0.026 (2)0.023 (2)0.027 (2)
C280.053 (2)0.069 (2)0.064 (3)0.0102 (18)0.0191 (19)0.009 (2)
C290.056 (2)0.139 (4)0.066 (3)0.019 (3)0.002 (2)0.022 (3)
C300.059 (2)0.0316 (15)0.0439 (19)0.0013 (13)0.0019 (16)0.0020 (14)
Geometric parameters (Å, º) top
Cu1—N11.902 (3)C8—H80.9300
Cu1—O11.910 (2)C9—C101.408 (5)
Cu1—N31.942 (3)C9—H90.9300
Cu1—N22.040 (3)C11—H110.9300
Cu2—O21.908 (2)C12—C131.498 (5)
Cu2—N41.926 (3)C12—H12A0.9700
Cu2—N61.945 (3)C12—H12B0.9700
Cu2—N52.056 (3)C13—H13A0.9700
S1—C151.620 (4)C13—H13B0.9700
S2—C301.621 (4)C14—H14A0.9600
O1—C21.309 (4)C14—H14B0.9600
O2—C171.295 (4)C14—H14C0.9600
N1—C111.287 (4)C16—C171.416 (4)
N1—C121.466 (4)C16—C261.423 (4)
N2—C131.462 (5)C16—C251.462 (4)
N2—C141.465 (5)C17—C181.424 (5)
N2—H20.91 (3)C18—C191.352 (5)
N3—C151.149 (4)C18—H180.9300
N4—C261.287 (4)C19—C201.415 (5)
N4—C271.469 (4)C19—H190.9300
N5—C291.459 (5)C20—C251.411 (4)
N5—C281.476 (5)C20—C211.417 (5)
N5—H50.90 (3)C21—C221.339 (6)
N6—C301.146 (4)C21—H210.9300
C1—C21.407 (4)C22—C231.400 (6)
C1—C111.426 (4)C22—H220.9300
C1—C101.457 (4)C23—C241.372 (5)
C2—C31.424 (4)C23—H230.9300
C3—C41.356 (5)C24—C251.406 (5)
C3—H30.9300C24—H240.9300
C4—C51.407 (5)C26—H260.9300
C4—H40.9300C27—C281.478 (5)
C5—C101.416 (4)C27—H27A0.9700
C5—C61.416 (5)C27—H27B0.9700
C6—C71.350 (5)C28—H28A0.9700
C6—H60.9300C28—H28B0.9700
C7—C81.393 (5)C29—H29A0.9600
C7—H70.9300C29—H29B0.9600
C8—C91.367 (5)C29—H29C0.9600
N1—Cu1—O192.43 (9)C13—C12—H12A110.2
N1—Cu1—N3174.58 (11)N1—C12—H12B110.2
O1—Cu1—N391.11 (11)C13—C12—H12B110.2
N1—Cu1—N284.82 (11)H12A—C12—H12B108.5
O1—Cu1—N2164.29 (11)N2—C13—C12110.1 (3)
N3—Cu1—N292.86 (13)N2—C13—H13A109.6
O2—Cu2—N491.11 (10)C12—C13—H13A109.6
O2—Cu2—N691.12 (11)N2—C13—H13B109.6
N4—Cu2—N6177.33 (12)C12—C13—H13B109.6
O2—Cu2—N5166.31 (12)H13A—C13—H13B108.2
N4—Cu2—N583.82 (11)N2—C14—H14A109.5
N6—Cu2—N594.32 (12)N2—C14—H14B109.5
C2—O1—Cu1127.74 (19)H14A—C14—H14B109.5
C17—O2—Cu2129.0 (2)N2—C14—H14C109.5
C11—N1—C12119.2 (3)H14A—C14—H14C109.5
C11—N1—Cu1127.3 (2)H14B—C14—H14C109.5
C12—N1—Cu1113.4 (2)N3—C15—S1177.8 (3)
C13—N2—C14115.0 (3)C17—C16—C26120.6 (3)
C13—N2—Cu1107.6 (2)C17—C16—C25119.9 (3)
C14—N2—Cu1116.5 (3)C26—C16—C25119.5 (3)
C13—N2—H2108 (3)O2—C17—C16125.1 (3)
C14—N2—H2103 (3)O2—C17—C18116.7 (3)
Cu1—N2—H2106 (3)C16—C17—C18118.2 (3)
C15—N3—Cu1171.1 (3)C19—C18—C17121.6 (3)
C26—N4—C27119.3 (3)C19—C18—H18119.2
C26—N4—Cu2127.7 (2)C17—C18—H18119.2
C27—N4—Cu2112.9 (2)C18—C19—C20122.4 (3)
C29—N5—C28110.5 (3)C18—C19—H19118.8
C29—N5—Cu2119.4 (3)C20—C19—H19118.8
C28—N5—Cu2105.9 (2)C25—C20—C19118.7 (3)
C29—N5—H5109 (3)C25—C20—C21119.4 (4)
C28—N5—H5116 (3)C19—C20—C21121.9 (3)
Cu2—N5—H596 (3)C22—C21—C20122.0 (4)
C30—N6—Cu2167.3 (3)C22—C21—H21119.0
C2—C1—C11121.3 (3)C20—C21—H21119.0
C2—C1—C10119.6 (3)C21—C22—C23119.3 (4)
C11—C1—C10119.1 (3)C21—C22—H22120.4
O1—C2—C1124.9 (3)C23—C22—H22120.4
O1—C2—C3116.5 (3)C24—C23—C22120.3 (4)
C1—C2—C3118.6 (3)C24—C23—H23119.9
C4—C3—C2121.9 (3)C22—C23—H23119.9
C4—C3—H3119.1C23—C24—C25122.0 (3)
C2—C3—H3119.1C23—C24—H24119.0
C3—C4—C5121.5 (3)C25—C24—H24119.0
C3—C4—H4119.3C24—C25—C20117.0 (3)
C5—C4—H4119.3C24—C25—C16123.8 (3)
C4—C5—C10119.2 (3)C20—C25—C16119.2 (3)
C4—C5—C6121.0 (3)N4—C26—C16126.2 (3)
C10—C5—C6119.7 (3)N4—C26—H26116.9
C7—C6—C5120.9 (3)C16—C26—H26116.9
C7—C6—H6119.6N4—C27—C28107.0 (3)
C5—C6—H6119.6N4—C27—H27A110.3
C6—C7—C8120.0 (3)C28—C27—H27A110.3
C6—C7—H7120.0N4—C27—H27B110.3
C8—C7—H7120.0C28—C27—H27B110.3
C9—C8—C7120.6 (4)H27A—C27—H27B108.6
C9—C8—H8119.7N5—C28—C27108.4 (3)
C7—C8—H8119.7N5—C28—H28A110.0
C8—C9—C10121.5 (3)C27—C28—H28A110.0
C8—C9—H9119.2N5—C28—H28B110.0
C10—C9—H9119.2C27—C28—H28B110.0
C9—C10—C5117.3 (3)H28A—C28—H28B108.4
C9—C10—C1123.5 (3)N5—C29—H29A109.5
C5—C10—C1119.2 (3)N5—C29—H29B109.5
N1—C11—C1126.3 (3)H29A—C29—H29B109.5
N1—C11—H11116.9N5—C29—H29C109.5
C1—C11—H11116.9H29A—C29—H29C109.5
N1—C12—C13107.4 (3)H29B—C29—H29C109.5
N1—C12—H12A110.2N6—C30—S2178.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.91 (3)2.07 (2)2.946 (4)162 (4)
N5—H5···S10.90 (3)2.78 (3)3.481 (3)135 (3)
Symmetry code: (i) x+1, y+1, z+1.
 

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