Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702538X/dn2173sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702538X/dn2173Isup2.hkl |
CCDC reference: 654684
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.035
- wR factor = 0.089
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 822.00 A 3
Author Response: The unit cell contains a certain amount of water molecules. However, these water molecules appear to be highly disordered and it was difficult to model their positions and distribution reliably. Therefore, the SQUEEZE function of PLATON (Sluis & Spek, 1990; Spek, 2003) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was emplyed from the final refinement. |
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N3A - C19A .. 7.05 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C13A - C19A .. 8.47 su
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.794 PLAT230_ALERT_2_C Hirshfeld Test Diff for S3A - O3A .. 6.15 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O2 .. 5.75 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S3A
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.25 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1A (2) 2.21
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
For related literature, see: Casella & Gullotti (1981, 1986); van der Sluis & Spek (1990); Spek (2003); Wang et al. (1994); Zhang & Jiang (2002).
H2L(0.05 g, 8 mmol), Cu(CH3COO)2 (0.18 g, 12 mmol) and phen(0.23 g,15 mmol), were added in a mixed solvent of dry ethanol and acetonitrile, the mixture was heated for 5 h under reflux and stirring. The resultant was then filtered to give a pure solution which was treated by diethyl ether. A week later, single crystals suitable for X-Ray diffraction analysis formed.
All H atoms were placed in calculated positions and treated as riding on their parent atoms with C—H = 0.93 Å (Caromatic), 0.97 Å (Cmethylene) or 0.98 Å (Cmethyl) and with Uiso(H) = 1.2Ueq(Caromatic, Cmethylene) or Uiso(H) = 1.5Ueq(Cmethyl).
Studies of Schiff base complexes containing sulfur and complexes of amino acid Schiff bases (Casella & Gullotti, 1981; Wang et al., 1994; Casella & Gullotti, 1986) have attracted increasing interest because of their antiviral, anticancer and antibacterial activities. Recently, Zhang & Jiang (2002) have reported a Schiff base complex derived from taurine, an amino acid containing sulfur. Compound (I) reported here represents a new Schiff base copper(II) complex.
The Cu1 atom in the title complex has a distorted square-pyramidal environment with the basal plane formed by two N atoms of the 2,2'-pyridine ligand [Cu1—N = 2.06 (3) Å] and one O atom and one N atom of the L ligand. [Cu1—O1 = 1.914 (3) Å and Cu1—N3 = 1.958 (3) Å]. The apical position is occupied by another O atom from the same L ligand. [Cu1—O2 = 2.286 (3) Å]. The asymmetric unit contains two such complexes which are interconnected by weak π-π interaction between the phenanthroline planes with interplanar distance of 3.675 Å and centroid to centroid vector of 3.455 Å leading to an offset of 19.9° (Fig. 1).
The unit cell contains a certain amount of water molecules. However, these water molecules appear to be highly disordered and it was difficult to model their positions and distribution reliably. Therefore, the SQUEEZE function of PLATON (van der Sluis & Spek, 1990; Spek, 2003) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was emplyed from the final refinement. Further details are given in the experimental section. Due to the omission of the water molecules from the model, it was not possible to analyse the hydrogen- bonding interactions.
For related literature, see: Casella & Gullotti (1981, 1986); van der Sluis & Spek (1990); Spek (2003); Wang et al. (1994); Zhang & Jiang (2002).
Data collection: SMART (Bruker,1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[Cu(C10H11NO5S)(C12H8N2)] | F(000) = 2056 |
Mr = 501.00 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8898 reflections |
a = 14.932 (1) Å | θ = 3.1–25.1° |
b = 26.6371 (17) Å | µ = 1.04 mm−1 |
c = 13.1937 (9) Å | T = 298 K |
β = 114.032 (1)° | Block, blue |
V = 4792.8 (6) Å3 | 0.20 × 0.18 × 0.18 mm |
Z = 8 |
Bruker APEX area-detector diffractometer | 8898 independent reflections |
Radiation source: fine-focus sealed tube | 4855 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ and ω scans | θmax = 25.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.817, Tmax = 0.833 | k = −32→31 |
30244 measured reflections | l = −15→15 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 0.79 | w = 1/[σ2(Fo2) + (0.0448P)2] where P = (Fo2 + 2Fc2)/3 |
8898 reflections | (Δ/σ)max = 0.002 |
579 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
[Cu(C10H11NO5S)(C12H8N2)] | V = 4792.8 (6) Å3 |
Mr = 501.00 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.932 (1) Å | µ = 1.04 mm−1 |
b = 26.6371 (17) Å | T = 298 K |
c = 13.1937 (9) Å | 0.20 × 0.18 × 0.18 mm |
β = 114.032 (1)° |
Bruker APEX area-detector diffractometer | 8898 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4855 reflections with I > 2σ(I) |
Tmin = 0.817, Tmax = 0.833 | Rint = 0.045 |
30244 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 0.79 | Δρmax = 0.25 e Å−3 |
8898 reflections | Δρmin = −0.22 e Å−3 |
579 parameters |
Experimental. There is one cavity of 820 Å3 per unitl cell. PLATON estimated that the cavity contains 105 electrons which may correspond to roughly 10 water molecules within the cell. This is contradictory with the size of the cavity in which we could expect to introduce roughly 40 water molecules i.e. roughly 10 water molecules within each asymmetric unit. It is well known that the SQUEEZE procedure is very dependent on the low-angle reflections and that the electron count may be underestimated if those reflections are missing which could be the case when data are collected on CCD machine. |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.06716 (3) | 0.858157 (14) | 0.41746 (3) | 0.04569 (13) | |
S3 | −0.03709 (7) | 0.76293 (3) | 0.47713 (7) | 0.0608 (3) | |
N1 | 0.19477 (18) | 0.85975 (9) | 0.5512 (2) | 0.0433 (6) | |
N2 | 0.15521 (18) | 0.81301 (9) | 0.3600 (2) | 0.0454 (7) | |
N3 | −0.06083 (18) | 0.85115 (9) | 0.29555 (19) | 0.0421 (6) | |
O1 | 0.06101 (14) | 0.93005 (7) | 0.41949 (17) | 0.0497 (6) | |
O2 | 0.02223 (16) | 0.80818 (8) | 0.51816 (17) | 0.0620 (7) | |
O3 | −0.0761 (2) | 0.74568 (11) | 0.5538 (2) | 0.0974 (10) | |
O4 | 0.09579 (16) | 1.02724 (8) | 0.4369 (2) | 0.0657 (7) | |
O5 | 0.0147 (2) | 0.72467 (10) | 0.4458 (2) | 0.1085 (11) | |
C1 | 0.1363 (3) | 0.79042 (12) | 0.2629 (3) | 0.0562 (9) | |
H1 | 0.0725 | 0.7916 | 0.2086 | 0.067* | |
C2 | 0.2064 (3) | 0.76553 (13) | 0.2390 (3) | 0.0673 (11) | |
H2 | 0.1891 | 0.7504 | 0.1701 | 0.081* | |
C3 | 0.2997 (3) | 0.76306 (13) | 0.3153 (3) | 0.0672 (11) | |
H3 | 0.3475 | 0.7468 | 0.2992 | 0.081* | |
C4 | 0.3235 (2) | 0.78553 (12) | 0.4195 (3) | 0.0529 (9) | |
C5 | 0.4197 (3) | 0.78579 (13) | 0.5064 (4) | 0.0685 (11) | |
H5 | 0.4703 | 0.7699 | 0.4952 | 0.082* | |
C6 | 0.4389 (3) | 0.80842 (14) | 0.6038 (3) | 0.0655 (11) | |
H6 | 0.5024 | 0.8077 | 0.6588 | 0.079* | |
C7 | 0.3642 (2) | 0.83352 (12) | 0.6249 (3) | 0.0480 (8) | |
C8 | 0.3787 (3) | 0.85810 (13) | 0.7246 (3) | 0.0608 (10) | |
H8 | 0.4403 | 0.8580 | 0.7832 | 0.073* | |
C9 | 0.3027 (3) | 0.88202 (13) | 0.7350 (3) | 0.0592 (10) | |
H9 | 0.3113 | 0.8979 | 0.8011 | 0.071* | |
C10 | 0.2115 (2) | 0.88243 (12) | 0.6452 (3) | 0.0539 (9) | |
H10 | 0.1602 | 0.8996 | 0.6525 | 0.065* | |
C11 | 0.2698 (2) | 0.83488 (11) | 0.5410 (2) | 0.0403 (8) | |
C12 | 0.2492 (2) | 0.81033 (11) | 0.4373 (3) | 0.0429 (8) | |
C13 | −0.0865 (2) | 0.94087 (11) | 0.2543 (2) | 0.0412 (8) | |
C14 | −0.0023 (2) | 0.95869 (11) | 0.3425 (2) | 0.0417 (8) | |
C15 | 0.0137 (2) | 1.01168 (11) | 0.3467 (3) | 0.0466 (8) | |
C16 | −0.0475 (2) | 1.04272 (12) | 0.2673 (3) | 0.0520 (9) | |
H16 | −0.0344 | 1.0770 | 0.2716 | 0.062* | |
C17 | −0.1294 (3) | 1.02408 (13) | 0.1798 (3) | 0.0581 (10) | |
H17 | −0.1702 | 1.0457 | 0.1251 | 0.070* | |
C18 | −0.1499 (2) | 0.97418 (13) | 0.1740 (3) | 0.0544 (9) | |
H18 | −0.2061 | 0.9619 | 0.1168 | 0.065* | |
C19 | −0.1122 (2) | 0.88848 (12) | 0.2405 (2) | 0.0434 (8) | |
H19 | −0.1733 | 0.8807 | 0.1852 | 0.052* | |
C20 | −0.1069 (2) | 0.80149 (11) | 0.2676 (3) | 0.0519 (9) | |
H20A | −0.0610 | 0.7782 | 0.2580 | 0.062* | |
H20B | −0.1639 | 0.8036 | 0.1976 | 0.062* | |
C21 | −0.1380 (2) | 0.78127 (12) | 0.3548 (3) | 0.0564 (9) | |
H21A | −0.1806 | 0.7526 | 0.3249 | 0.068* | |
H21B | −0.1752 | 0.8068 | 0.3732 | 0.068* | |
C22 | 0.1063 (3) | 1.07918 (12) | 0.4594 (3) | 0.0679 (11) | |
H22A | 0.0482 | 1.0918 | 0.4650 | 0.102* | |
H22B | 0.1158 | 1.0962 | 0.4004 | 0.102* | |
H22C | 0.1619 | 1.0849 | 0.5281 | 0.102* | |
Cu1A | 0.64785 (3) | 0.963637 (14) | 0.76034 (3) | 0.04578 (12) | |
S3A | 0.68734 (7) | 0.85167 (4) | 0.89860 (9) | 0.0639 (3) | |
N1A | 0.5971 (2) | 0.93262 (9) | 0.6028 (2) | 0.0478 (7) | |
N2A | 0.50451 (18) | 0.97952 (9) | 0.7082 (2) | 0.0437 (6) | |
N3A | 0.78552 (19) | 0.94433 (10) | 0.8101 (2) | 0.0486 (7) | |
O1A | 0.68059 (15) | 1.02090 (7) | 0.85712 (17) | 0.0492 (6) | |
O2A | 0.62862 (16) | 0.89728 (8) | 0.8594 (2) | 0.0717 (7) | |
O3A | 0.69166 (19) | 0.83556 (10) | 1.0061 (2) | 0.0919 (9) | |
O4A | 0.67704 (19) | 1.11313 (8) | 0.9188 (2) | 0.0728 (7) | |
O5A | 0.6580 (2) | 0.81301 (10) | 0.8164 (2) | 0.1016 (10) | |
C1A | 0.6446 (3) | 0.91202 (13) | 0.5493 (3) | 0.0636 (10) | |
H1A | 0.7125 | 0.9096 | 0.5842 | 0.076* | |
C2A | 0.5959 (3) | 0.89336 (14) | 0.4402 (3) | 0.0721 (11) | |
H2A | 0.6318 | 0.8786 | 0.4048 | 0.087* | |
C3A | 0.4992 (3) | 0.89691 (13) | 0.3882 (3) | 0.0656 (11) | |
H3A | 0.4674 | 0.8846 | 0.3163 | 0.079* | |
C4A | 0.4457 (3) | 0.91880 (12) | 0.4403 (3) | 0.0524 (9) | |
C5A | 0.3416 (3) | 0.92501 (13) | 0.3925 (3) | 0.0654 (11) | |
H5A | 0.3056 | 0.9124 | 0.3217 | 0.078* | |
C6A | 0.2941 (3) | 0.94820 (13) | 0.4455 (3) | 0.0630 (10) | |
H6A | 0.2264 | 0.9518 | 0.4107 | 0.076* | |
C7A | 0.3460 (2) | 0.96773 (12) | 0.5555 (3) | 0.0499 (9) | |
C8A | 0.3022 (3) | 0.99224 (13) | 0.6163 (3) | 0.0613 (10) | |
H8A | 0.2345 | 0.9962 | 0.5868 | 0.074* | |
C9A | 0.3587 (3) | 1.01060 (13) | 0.7198 (3) | 0.0594 (10) | |
H9A | 0.3300 | 1.0275 | 0.7606 | 0.071* | |
C10A | 0.4595 (2) | 1.00356 (12) | 0.7630 (3) | 0.0541 (9) | |
H10A | 0.4974 | 1.0162 | 0.8333 | 0.065* | |
C11A | 0.4485 (2) | 0.96168 (11) | 0.6052 (2) | 0.0417 (8) | |
C12A | 0.4978 (2) | 0.93712 (11) | 0.5483 (2) | 0.0423 (8) | |
C13A | 0.8456 (2) | 1.02885 (12) | 0.8696 (3) | 0.0456 (8) | |
C14A | 0.7607 (2) | 1.04753 (12) | 0.8784 (2) | 0.0441 (8) | |
C15A | 0.7620 (3) | 1.09791 (12) | 0.9134 (3) | 0.0513 (9) | |
C16A | 0.8427 (3) | 1.12763 (14) | 0.9370 (3) | 0.0677 (11) | |
H16A | 0.8420 | 1.1606 | 0.9598 | 0.081* | |
C17A | 0.9265 (3) | 1.10881 (16) | 0.9272 (3) | 0.0790 (13) | |
H17A | 0.9807 | 1.1294 | 0.9424 | 0.095* | |
C18A | 0.9283 (3) | 1.05996 (16) | 0.8951 (3) | 0.0680 (11) | |
H18A | 0.9844 | 1.0473 | 0.8902 | 0.082* | |
C19A | 0.8546 (2) | 0.97739 (14) | 0.8474 (3) | 0.0554 (10) | |
H19A | 0.9175 | 0.9662 | 0.8612 | 0.066* | |
C20A | 0.8158 (3) | 0.89156 (13) | 0.8196 (3) | 0.0638 (10) | |
H20C | 0.8830 | 0.8894 | 0.8269 | 0.077* | |
H20D | 0.7745 | 0.8736 | 0.7529 | 0.077* | |
C21A | 0.8076 (2) | 0.86740 (12) | 0.9202 (3) | 0.0568 (10) | |
H21C | 0.8339 | 0.8904 | 0.9825 | 0.068* | |
H21D | 0.8475 | 0.8372 | 0.9398 | 0.068* | |
C22A | 0.6742 (3) | 1.16233 (14) | 0.9612 (4) | 0.1031 (16) | |
H22D | 0.7251 | 1.1654 | 1.0346 | 0.155* | |
H22E | 0.6116 | 1.1677 | 0.9638 | 0.155* | |
H22F | 0.6840 | 1.1870 | 0.9136 | 0.155* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0392 (2) | 0.0416 (2) | 0.0400 (2) | 0.00257 (19) | −0.00042 (18) | −0.00068 (18) |
S3 | 0.0617 (6) | 0.0527 (6) | 0.0482 (6) | −0.0084 (5) | 0.0022 (5) | 0.0131 (5) |
N1 | 0.0420 (16) | 0.0432 (15) | 0.0336 (15) | −0.0023 (13) | 0.0041 (13) | −0.0023 (13) |
N2 | 0.0447 (17) | 0.0425 (15) | 0.0376 (16) | 0.0022 (13) | 0.0053 (13) | −0.0015 (13) |
N3 | 0.0419 (16) | 0.0423 (16) | 0.0326 (14) | −0.0017 (13) | 0.0056 (12) | 0.0019 (12) |
O1 | 0.0420 (13) | 0.0384 (12) | 0.0523 (14) | 0.0025 (10) | 0.0024 (11) | 0.0036 (10) |
O2 | 0.0586 (15) | 0.0613 (15) | 0.0440 (13) | −0.0193 (12) | −0.0019 (12) | 0.0098 (11) |
O3 | 0.089 (2) | 0.123 (2) | 0.0590 (17) | −0.0396 (18) | 0.0090 (16) | 0.0348 (16) |
O4 | 0.0532 (15) | 0.0359 (14) | 0.0852 (18) | 0.0046 (11) | 0.0048 (14) | −0.0028 (12) |
O5 | 0.129 (3) | 0.0715 (19) | 0.092 (2) | 0.0495 (19) | 0.011 (2) | 0.0101 (16) |
C1 | 0.053 (2) | 0.054 (2) | 0.053 (2) | −0.0012 (19) | 0.0121 (19) | −0.0049 (19) |
C2 | 0.078 (3) | 0.061 (2) | 0.063 (3) | 0.002 (2) | 0.028 (2) | −0.018 (2) |
C3 | 0.062 (3) | 0.057 (2) | 0.081 (3) | 0.010 (2) | 0.027 (2) | −0.009 (2) |
C4 | 0.047 (2) | 0.042 (2) | 0.065 (2) | 0.0038 (17) | 0.0168 (19) | 0.0019 (18) |
C5 | 0.049 (2) | 0.060 (2) | 0.089 (3) | 0.015 (2) | 0.020 (2) | 0.003 (2) |
C6 | 0.041 (2) | 0.066 (3) | 0.069 (3) | 0.0058 (19) | 0.001 (2) | 0.008 (2) |
C7 | 0.037 (2) | 0.0455 (19) | 0.046 (2) | −0.0023 (17) | 0.0009 (17) | 0.0078 (17) |
C8 | 0.049 (2) | 0.064 (2) | 0.047 (2) | −0.012 (2) | −0.0034 (18) | 0.0110 (19) |
C9 | 0.062 (3) | 0.067 (2) | 0.035 (2) | −0.010 (2) | 0.0066 (19) | −0.0051 (17) |
C10 | 0.049 (2) | 0.060 (2) | 0.046 (2) | −0.0028 (18) | 0.0119 (18) | −0.0044 (18) |
C11 | 0.0384 (19) | 0.0325 (17) | 0.041 (2) | −0.0019 (15) | 0.0074 (16) | 0.0053 (15) |
C12 | 0.0387 (19) | 0.0364 (18) | 0.045 (2) | −0.0009 (15) | 0.0081 (17) | 0.0070 (15) |
C13 | 0.0371 (18) | 0.047 (2) | 0.0353 (18) | 0.0059 (16) | 0.0103 (15) | 0.0061 (15) |
C14 | 0.0407 (19) | 0.0435 (19) | 0.0399 (19) | 0.0064 (16) | 0.0155 (16) | 0.0068 (16) |
C15 | 0.042 (2) | 0.043 (2) | 0.053 (2) | 0.0030 (17) | 0.0172 (18) | 0.0033 (17) |
C16 | 0.055 (2) | 0.0415 (19) | 0.061 (2) | 0.0106 (18) | 0.025 (2) | 0.0106 (18) |
C17 | 0.060 (2) | 0.053 (2) | 0.055 (2) | 0.0226 (19) | 0.018 (2) | 0.0174 (18) |
C18 | 0.045 (2) | 0.064 (2) | 0.046 (2) | 0.0144 (18) | 0.0101 (17) | 0.0103 (18) |
C19 | 0.0333 (18) | 0.056 (2) | 0.0326 (18) | 0.0023 (17) | 0.0046 (15) | 0.0030 (16) |
C20 | 0.051 (2) | 0.048 (2) | 0.039 (2) | −0.0059 (17) | −0.0001 (17) | −0.0016 (16) |
C21 | 0.048 (2) | 0.051 (2) | 0.051 (2) | −0.0115 (17) | 0.0008 (17) | 0.0095 (17) |
C22 | 0.063 (3) | 0.046 (2) | 0.089 (3) | −0.0012 (19) | 0.025 (2) | −0.002 (2) |
Cu1A | 0.0351 (2) | 0.0491 (2) | 0.0476 (2) | −0.00128 (19) | 0.01125 (19) | −0.00943 (19) |
S3A | 0.0467 (6) | 0.0552 (6) | 0.0697 (7) | −0.0005 (5) | 0.0031 (5) | 0.0013 (5) |
N1A | 0.0500 (18) | 0.0486 (17) | 0.0471 (17) | −0.0013 (14) | 0.0222 (15) | −0.0049 (13) |
N2A | 0.0374 (15) | 0.0434 (15) | 0.0457 (17) | 0.0016 (13) | 0.0123 (14) | −0.0012 (13) |
N3A | 0.0394 (16) | 0.0530 (17) | 0.0519 (17) | 0.0025 (14) | 0.0171 (14) | −0.0069 (14) |
O1A | 0.0411 (13) | 0.0499 (13) | 0.0587 (14) | −0.0110 (11) | 0.0224 (11) | −0.0146 (11) |
O2A | 0.0488 (15) | 0.0647 (16) | 0.099 (2) | 0.0157 (13) | 0.0271 (14) | 0.0239 (14) |
O3A | 0.0751 (19) | 0.107 (2) | 0.083 (2) | 0.0028 (17) | 0.0221 (16) | 0.0364 (17) |
O4A | 0.081 (2) | 0.0526 (16) | 0.0906 (19) | −0.0076 (14) | 0.0406 (16) | −0.0209 (14) |
O5A | 0.078 (2) | 0.0791 (19) | 0.107 (2) | −0.0147 (16) | −0.0043 (17) | −0.0279 (18) |
C1A | 0.067 (3) | 0.070 (3) | 0.057 (3) | 0.004 (2) | 0.028 (2) | −0.004 (2) |
C2A | 0.100 (4) | 0.070 (3) | 0.057 (3) | 0.003 (3) | 0.043 (3) | −0.011 (2) |
C3A | 0.084 (3) | 0.060 (2) | 0.045 (2) | −0.011 (2) | 0.019 (2) | −0.0082 (19) |
C4A | 0.066 (3) | 0.045 (2) | 0.040 (2) | −0.0118 (19) | 0.016 (2) | 0.0037 (17) |
C5A | 0.074 (3) | 0.063 (3) | 0.037 (2) | −0.021 (2) | 0.000 (2) | 0.0060 (19) |
C6A | 0.051 (2) | 0.064 (2) | 0.051 (2) | −0.010 (2) | −0.002 (2) | 0.014 (2) |
C7A | 0.042 (2) | 0.049 (2) | 0.048 (2) | −0.0034 (17) | 0.0075 (18) | 0.0126 (17) |
C8A | 0.039 (2) | 0.070 (3) | 0.065 (3) | 0.0055 (19) | 0.012 (2) | 0.020 (2) |
C9A | 0.050 (2) | 0.064 (2) | 0.070 (3) | 0.0131 (19) | 0.030 (2) | 0.008 (2) |
C10A | 0.046 (2) | 0.063 (2) | 0.047 (2) | 0.0052 (18) | 0.0130 (18) | 0.0007 (18) |
C11A | 0.0404 (19) | 0.0383 (18) | 0.0389 (19) | −0.0056 (16) | 0.0084 (16) | 0.0051 (15) |
C12A | 0.045 (2) | 0.0391 (18) | 0.037 (2) | −0.0091 (16) | 0.0117 (17) | 0.0044 (15) |
C13A | 0.0373 (19) | 0.052 (2) | 0.0427 (19) | −0.0088 (17) | 0.0113 (16) | 0.0041 (16) |
C14A | 0.043 (2) | 0.050 (2) | 0.0319 (18) | −0.0062 (17) | 0.0082 (16) | 0.0042 (15) |
C15A | 0.054 (2) | 0.051 (2) | 0.043 (2) | −0.0094 (19) | 0.0141 (18) | −0.0037 (17) |
C16A | 0.071 (3) | 0.052 (2) | 0.060 (2) | −0.016 (2) | 0.005 (2) | 0.0029 (18) |
C17A | 0.050 (3) | 0.072 (3) | 0.089 (3) | −0.022 (2) | 0.001 (2) | 0.018 (2) |
C18A | 0.042 (2) | 0.085 (3) | 0.065 (3) | −0.007 (2) | 0.0101 (19) | 0.019 (2) |
C19A | 0.035 (2) | 0.086 (3) | 0.045 (2) | 0.009 (2) | 0.0172 (17) | 0.006 (2) |
C20A | 0.050 (2) | 0.069 (3) | 0.071 (3) | 0.009 (2) | 0.023 (2) | −0.018 (2) |
C21A | 0.040 (2) | 0.049 (2) | 0.068 (2) | 0.0081 (17) | 0.0073 (18) | −0.0059 (18) |
C22A | 0.134 (4) | 0.054 (3) | 0.138 (4) | −0.008 (3) | 0.072 (4) | −0.030 (3) |
Cu1—O1 | 1.918 (2) | Cu1A—O1A | 1.9204 (19) |
Cu1—N3 | 1.942 (2) | Cu1A—N3A | 1.955 (3) |
Cu1—N1 | 2.002 (2) | Cu1A—N2A | 2.008 (3) |
Cu1—N2 | 2.136 (3) | Cu1A—N1A | 2.072 (3) |
Cu1—O2 | 2.171 (2) | Cu1A—O2A | 2.285 (2) |
S3—O3 | 1.433 (3) | S3A—O5A | 1.429 (3) |
S3—O5 | 1.438 (3) | S3A—O3A | 1.457 (3) |
S3—O2 | 1.463 (2) | S3A—O2A | 1.464 (2) |
S3—C21 | 1.770 (3) | S3A—C21A | 1.751 (3) |
N1—C10 | 1.310 (4) | N1A—C1A | 1.307 (4) |
N1—C11 | 1.355 (4) | N1A—C12A | 1.364 (4) |
N2—C1 | 1.337 (4) | N2A—C10A | 1.334 (4) |
N2—C12 | 1.360 (4) | N2A—C11A | 1.359 (4) |
N3—C19 | 1.285 (3) | N3A—C19A | 1.292 (4) |
N3—C20 | 1.467 (4) | N3A—C20A | 1.466 (4) |
O1—C14 | 1.314 (3) | O1A—C14A | 1.318 (3) |
O4—C15 | 1.380 (4) | O4A—C15A | 1.360 (4) |
O4—C22 | 1.410 (3) | O4A—C22A | 1.432 (4) |
C1—C2 | 1.379 (4) | C1A—C2A | 1.413 (5) |
C1—H1 | 0.9300 | C1A—H1A | 0.9300 |
C2—C3 | 1.348 (5) | C2A—C3A | 1.326 (5) |
C2—H2 | 0.9300 | C2A—H2A | 0.9300 |
C3—C4 | 1.407 (5) | C3A—C4A | 1.378 (5) |
C3—H3 | 0.9300 | C3A—H3A | 0.9300 |
C4—C12 | 1.391 (4) | C4A—C12A | 1.405 (4) |
C4—C5 | 1.427 (5) | C4A—C5A | 1.429 (5) |
C5—C6 | 1.340 (5) | C5A—C6A | 1.333 (5) |
C5—H5 | 0.9300 | C5A—H5A | 0.9300 |
C6—C7 | 1.422 (5) | C6A—C7A | 1.436 (5) |
C6—H6 | 0.9300 | C6A—H6A | 0.9300 |
C7—C11 | 1.393 (4) | C7A—C8A | 1.388 (5) |
C7—C8 | 1.405 (5) | C7A—C11A | 1.408 (4) |
C8—C9 | 1.357 (5) | C8A—C9A | 1.370 (5) |
C8—H8 | 0.9300 | C8A—H8A | 0.9300 |
C9—C10 | 1.394 (4) | C9A—C10A | 1.388 (4) |
C9—H9 | 0.9300 | C9A—H9A | 0.9300 |
C10—H10 | 0.9300 | C10A—H10A | 0.9300 |
C11—C12 | 1.432 (4) | C11A—C12A | 1.408 (4) |
C13—C14 | 1.403 (4) | C13A—C18A | 1.409 (4) |
C13—C18 | 1.410 (4) | C13A—C14A | 1.411 (4) |
C13—C19 | 1.439 (4) | C13A—C19A | 1.420 (4) |
C14—C15 | 1.429 (4) | C14A—C15A | 1.417 (4) |
C15—C16 | 1.354 (4) | C15A—C16A | 1.368 (4) |
C16—C17 | 1.388 (4) | C16A—C17A | 1.402 (5) |
C16—H16 | 0.9300 | C16A—H16A | 0.9300 |
C17—C18 | 1.359 (4) | C17A—C18A | 1.372 (5) |
C17—H17 | 0.9300 | C17A—H17A | 0.9300 |
C18—H18 | 0.9300 | C18A—H18A | 0.9300 |
C19—H19 | 0.9300 | C19A—H19A | 0.9300 |
C20—C21 | 1.505 (4) | C20A—C21A | 1.525 (4) |
C20—H20A | 0.9700 | C20A—H20C | 0.9700 |
C20—H20B | 0.9700 | C20A—H20D | 0.9700 |
C21—H21A | 0.9700 | C21A—H21C | 0.9700 |
C21—H21B | 0.9700 | C21A—H21D | 0.9700 |
C22—H22A | 0.9600 | C22A—H22D | 0.9600 |
C22—H22B | 0.9600 | C22A—H22E | 0.9600 |
C22—H22C | 0.9600 | C22A—H22F | 0.9600 |
O1—Cu1—N3 | 94.07 (9) | O1A—Cu1A—N3A | 92.14 (10) |
O1—Cu1—N1 | 90.02 (9) | O1A—Cu1A—N2A | 90.44 (10) |
N3—Cu1—N1 | 174.02 (10) | N3A—Cu1A—N2A | 176.90 (11) |
O1—Cu1—N2 | 127.37 (9) | O1A—Cu1A—N1A | 150.90 (9) |
N3—Cu1—N2 | 101.09 (10) | N3A—Cu1A—N1A | 97.89 (11) |
N1—Cu1—N2 | 79.75 (10) | N2A—Cu1A—N1A | 80.62 (11) |
O1—Cu1—O2 | 125.12 (9) | O1A—Cu1A—O2A | 106.94 (9) |
N3—Cu1—O2 | 90.16 (9) | N3A—Cu1A—O2A | 87.95 (10) |
N1—Cu1—O2 | 83.92 (9) | N2A—Cu1A—O2A | 89.66 (9) |
N2—Cu1—O2 | 105.09 (9) | N1A—Cu1A—O2A | 100.69 (9) |
O3—S3—O5 | 113.38 (19) | O5A—S3A—O3A | 113.86 (18) |
O3—S3—O2 | 111.21 (16) | O5A—S3A—O2A | 112.07 (16) |
O5—S3—O2 | 111.99 (18) | O3A—S3A—O2A | 111.78 (16) |
O3—S3—C21 | 107.01 (16) | O5A—S3A—C21A | 105.85 (18) |
O5—S3—C21 | 106.94 (17) | O3A—S3A—C21A | 106.01 (17) |
O2—S3—C21 | 105.80 (14) | O2A—S3A—C21A | 106.63 (15) |
C10—N1—C11 | 118.2 (3) | C1A—N1A—C12A | 117.7 (3) |
C10—N1—Cu1 | 126.2 (2) | C1A—N1A—Cu1A | 130.7 (2) |
C11—N1—Cu1 | 115.6 (2) | C12A—N1A—Cu1A | 111.6 (2) |
C1—N2—C12 | 116.5 (3) | C10A—N2A—C11A | 118.0 (3) |
C1—N2—Cu1 | 132.3 (2) | C10A—N2A—Cu1A | 128.1 (2) |
C12—N2—Cu1 | 111.1 (2) | C11A—N2A—Cu1A | 113.9 (2) |
C19—N3—C20 | 116.4 (2) | C19A—N3A—C20A | 116.8 (3) |
C19—N3—Cu1 | 123.6 (2) | C19A—N3A—Cu1A | 121.1 (2) |
C20—N3—Cu1 | 119.82 (19) | C20A—N3A—Cu1A | 121.8 (2) |
C14—O1—Cu1 | 126.34 (19) | C14A—O1A—Cu1A | 122.17 (19) |
S3—O2—Cu1 | 124.76 (13) | S3A—O2A—Cu1A | 130.35 (14) |
C15—O4—C22 | 117.4 (3) | C15A—O4A—C22A | 118.0 (3) |
N2—C1—C2 | 123.4 (3) | N1A—C1A—C2A | 122.1 (4) |
N2—C1—H1 | 118.3 | N1A—C1A—H1A | 119.0 |
C2—C1—H1 | 118.3 | C2A—C1A—H1A | 119.0 |
C3—C2—C1 | 120.2 (4) | C3A—C2A—C1A | 120.1 (4) |
C3—C2—H2 | 119.9 | C3A—C2A—H2A | 119.9 |
C1—C2—H2 | 119.9 | C1A—C2A—H2A | 119.9 |
C2—C3—C4 | 118.8 (3) | C2A—C3A—C4A | 120.2 (4) |
C2—C3—H3 | 120.6 | C2A—C3A—H3A | 119.9 |
C4—C3—H3 | 120.6 | C4A—C3A—H3A | 119.9 |
C12—C4—C3 | 117.8 (3) | C3A—C4A—C12A | 117.4 (3) |
C12—C4—C5 | 118.2 (3) | C3A—C4A—C5A | 125.2 (4) |
C3—C4—C5 | 123.9 (3) | C12A—C4A—C5A | 117.4 (3) |
C6—C5—C4 | 121.7 (4) | C6A—C5A—C4A | 122.5 (3) |
C6—C5—H5 | 119.2 | C6A—C5A—H5A | 118.7 |
C4—C5—H5 | 119.2 | C4A—C5A—H5A | 118.7 |
C5—C6—C7 | 121.3 (3) | C5A—C6A—C7A | 121.0 (3) |
C5—C6—H6 | 119.3 | C5A—C6A—H6A | 119.5 |
C7—C6—H6 | 119.3 | C7A—C6A—H6A | 119.5 |
C11—C7—C8 | 116.9 (3) | C8A—C7A—C11A | 117.6 (3) |
C11—C7—C6 | 118.5 (3) | C8A—C7A—C6A | 124.6 (3) |
C8—C7—C6 | 124.6 (3) | C11A—C7A—C6A | 117.8 (3) |
C9—C8—C7 | 119.8 (3) | C9A—C8A—C7A | 120.0 (3) |
C9—C8—H8 | 120.1 | C9A—C8A—H8A | 120.0 |
C7—C8—H8 | 120.1 | C7A—C8A—H8A | 120.0 |
C8—C9—C10 | 119.0 (3) | C8A—C9A—C10A | 119.1 (3) |
C8—C9—H9 | 120.5 | C8A—C9A—H9A | 120.5 |
C10—C9—H9 | 120.5 | C10A—C9A—H9A | 120.5 |
N1—C10—C9 | 123.0 (3) | N2A—C10A—C9A | 122.9 (3) |
N1—C10—H10 | 118.5 | N2A—C10A—H10A | 118.5 |
C9—C10—H10 | 118.5 | C9A—C10A—H10A | 118.5 |
N1—C11—C7 | 123.0 (3) | N2A—C11A—C12A | 117.0 (3) |
N1—C11—C12 | 116.9 (3) | N2A—C11A—C7A | 122.3 (3) |
C7—C11—C12 | 120.1 (3) | C12A—C11A—C7A | 120.7 (3) |
N2—C12—C4 | 123.3 (3) | N1A—C12A—C4A | 122.6 (3) |
N2—C12—C11 | 116.6 (3) | N1A—C12A—C11A | 116.9 (3) |
C4—C12—C11 | 120.1 (3) | C4A—C12A—C11A | 120.6 (3) |
C14—C13—C18 | 120.7 (3) | C18A—C13A—C14A | 120.2 (3) |
C14—C13—C19 | 122.4 (3) | C18A—C13A—C19A | 118.0 (3) |
C18—C13—C19 | 116.9 (3) | C14A—C13A—C19A | 121.5 (3) |
O1—C14—C13 | 124.4 (3) | O1A—C14A—C13A | 124.1 (3) |
O1—C14—C15 | 119.2 (3) | O1A—C14A—C15A | 118.0 (3) |
C13—C14—C15 | 116.4 (3) | C13A—C14A—C15A | 117.9 (3) |
C16—C15—O4 | 124.5 (3) | O4A—C15A—C16A | 124.7 (3) |
C16—C15—C14 | 121.6 (3) | O4A—C15A—C14A | 114.2 (3) |
O4—C15—C14 | 113.9 (3) | C16A—C15A—C14A | 121.1 (4) |
C15—C16—C17 | 120.9 (3) | C15A—C16A—C17A | 120.6 (4) |
C15—C16—H16 | 119.6 | C15A—C16A—H16A | 119.7 |
C17—C16—H16 | 119.6 | C17A—C16A—H16A | 119.7 |
C18—C17—C16 | 119.9 (3) | C18A—C17A—C16A | 119.9 (4) |
C18—C17—H17 | 120.1 | C18A—C17A—H17A | 120.1 |
C16—C17—H17 | 120.1 | C16A—C17A—H17A | 120.1 |
C17—C18—C13 | 120.4 (3) | C17A—C18A—C13A | 120.4 (4) |
C17—C18—H18 | 119.8 | C17A—C18A—H18A | 119.8 |
C13—C18—H18 | 119.8 | C13A—C18A—H18A | 119.8 |
N3—C19—C13 | 127.7 (3) | N3A—C19A—C13A | 127.5 (3) |
N3—C19—H19 | 116.1 | N3A—C19A—H19A | 116.3 |
C13—C19—H19 | 116.1 | C13A—C19A—H19A | 116.3 |
N3—C20—C21 | 112.9 (3) | N3A—C20A—C21A | 110.3 (3) |
N3—C20—H20A | 109.0 | N3A—C20A—H20C | 109.6 |
C21—C20—H20A | 109.0 | C21A—C20A—H20C | 109.6 |
N3—C20—H20B | 109.0 | N3A—C20A—H20D | 109.6 |
C21—C20—H20B | 109.0 | C21A—C20A—H20D | 109.6 |
H20A—C20—H20B | 107.8 | H20C—C20A—H20D | 108.1 |
C20—C21—S3 | 112.5 (2) | C20A—C21A—S3A | 113.6 (2) |
C20—C21—H21A | 109.1 | C20A—C21A—H21C | 108.9 |
S3—C21—H21A | 109.1 | S3A—C21A—H21C | 108.9 |
C20—C21—H21B | 109.1 | C20A—C21A—H21D | 108.9 |
S3—C21—H21B | 109.1 | S3A—C21A—H21D | 108.9 |
H21A—C21—H21B | 107.8 | H21C—C21A—H21D | 107.7 |
O4—C22—H22A | 109.5 | O4A—C22A—H22D | 109.5 |
O4—C22—H22B | 109.5 | O4A—C22A—H22E | 109.5 |
H22A—C22—H22B | 109.5 | H22D—C22A—H22E | 109.5 |
O4—C22—H22C | 109.5 | O4A—C22A—H22F | 109.5 |
H22A—C22—H22C | 109.5 | H22D—C22A—H22F | 109.5 |
H22B—C22—H22C | 109.5 | H22E—C22A—H22F | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Cu(C10H11NO5S)(C12H8N2)] |
Mr | 501.00 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 14.932 (1), 26.6371 (17), 13.1937 (9) |
β (°) | 114.032 (1) |
V (Å3) | 4792.8 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.04 |
Crystal size (mm) | 0.20 × 0.18 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.817, 0.833 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30244, 8898, 4855 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.089, 0.79 |
No. of reflections | 8898 |
No. of parameters | 579 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.22 |
Computer programs: SMART (Bruker,1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
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Studies of Schiff base complexes containing sulfur and complexes of amino acid Schiff bases (Casella & Gullotti, 1981; Wang et al., 1994; Casella & Gullotti, 1986) have attracted increasing interest because of their antiviral, anticancer and antibacterial activities. Recently, Zhang & Jiang (2002) have reported a Schiff base complex derived from taurine, an amino acid containing sulfur. Compound (I) reported here represents a new Schiff base copper(II) complex.
The Cu1 atom in the title complex has a distorted square-pyramidal environment with the basal plane formed by two N atoms of the 2,2'-pyridine ligand [Cu1—N = 2.06 (3) Å] and one O atom and one N atom of the L ligand. [Cu1—O1 = 1.914 (3) Å and Cu1—N3 = 1.958 (3) Å]. The apical position is occupied by another O atom from the same L ligand. [Cu1—O2 = 2.286 (3) Å]. The asymmetric unit contains two such complexes which are interconnected by weak π-π interaction between the phenanthroline planes with interplanar distance of 3.675 Å and centroid to centroid vector of 3.455 Å leading to an offset of 19.9° (Fig. 1).
The unit cell contains a certain amount of water molecules. However, these water molecules appear to be highly disordered and it was difficult to model their positions and distribution reliably. Therefore, the SQUEEZE function of PLATON (van der Sluis & Spek, 1990; Spek, 2003) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was emplyed from the final refinement. Further details are given in the experimental section. Due to the omission of the water molecules from the model, it was not possible to analyse the hydrogen- bonding interactions.