Treatment of deprotonated
N,
N′-bis-(4-methyl-2-benzothiazolyl)-2,6-pyridicarboxamide (
L2−) with CuCl
2·2H
2O yields the mononuclear title complex, Cu
L(H
2O) or [Cu(C
23H
15N
5O
2S
2)(H
2O)]. The Cu
II atom adopts a distorted square-planar coordination geometry, binding to two deprotonated amide N atoms, the pyridine N atom and the water O atom. In the crystal structure, weak C—H
O and C—H
S hydrogen bonds, and C—H
π and π–π interactions stabilize the crystal structure.
Supporting information
CCDC reference: 647334
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.006 Å
- R factor = 0.058
- wR factor = 0.097
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: XSCANS (Bruker, 2000); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Aqua[
N,
N'-bis(4-methyl-1,3-benzothiazol-2-yl)pyridine-2,6-
dicarboxamidato(2-)]copper(II)
top
Crystal data top
[Cu(C23H15N5O2S2)(H2O)] | Z = 2 |
Mr = 539.11 | F(000) = 550 |
Triclinic, P1 | Dx = 1.660 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7570 (11) Å | Cell parameters from 737 reflections |
b = 11.208 (2) Å | θ = 2.1–25.4° |
c = 11.302 (2) Å | µ = 1.25 mm−1 |
α = 89.910 (3)° | T = 291 K |
β = 76.450 (3)° | Block, brown |
γ = 89.530 (3)° | 0.30 × 0.26 × 0.24 mm |
V = 1078.4 (3) Å3 | |
Data collection top
Siemens P4 diffractometer | 3302 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
2θ/ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −13→13 |
Tmin = 0.70, Tmax = 0.74 | l = −13→13 |
7899 measured reflections | 3 standard reflections every 97 reflections |
4243 independent reflections | intensity decay: 0.01% |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0323P)2 + 0.7096P] where P = (Fo2 + 2Fc2)/3 |
4243 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
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 | |
C1 | −0.1186 (4) | 0.2914 (3) | 0.9964 (3) | 0.0388 (8) | |
C2 | −0.2187 (4) | 0.2823 (4) | 1.1100 (3) | 0.0460 (9) | |
H2 | −0.1929 | 0.3160 | 1.1779 | 0.055* | |
C3 | −0.3609 (5) | 0.2207 (4) | 1.1207 (4) | 0.0565 (10) | |
H3 | −0.4303 | 0.2140 | 1.1965 | 0.068* | |
C4 | −0.3983 (4) | 0.1704 (4) | 1.0201 (3) | 0.0488 (9) | |
H4 | −0.4922 | 0.1299 | 1.0269 | 0.059* | |
C5 | −0.2930 (4) | 0.1817 (3) | 0.9096 (3) | 0.0392 (8) | |
C6 | 0.0429 (4) | 0.3462 (3) | 0.9667 (3) | 0.0383 (7) | |
C7 | 0.2706 (4) | 0.3653 (3) | 0.8045 (3) | 0.0351 (7) | |
C8 | 0.4976 (4) | 0.3843 (3) | 0.6706 (3) | 0.0349 (7) | |
C9 | 0.6046 (5) | 0.3789 (3) | 0.5568 (3) | 0.0468 (9) | |
C10 | 0.7548 (5) | 0.4240 (3) | 0.5506 (4) | 0.0536 (10) | |
H10 | 0.8284 | 0.4216 | 0.4765 | 0.064* | |
C11 | 0.7983 (4) | 0.4724 (4) | 0.6514 (4) | 0.0567 (11) | |
H11 | 0.8999 | 0.5008 | 0.6424 | 0.068* | |
C12 | 0.6950 (5) | 0.4795 (4) | 0.7639 (4) | 0.0532 (10) | |
H12 | 0.7233 | 0.5128 | 0.8310 | 0.064* | |
C13 | 0.5437 (4) | 0.4328 (3) | 0.7711 (3) | 0.0403 (8) | |
C14 | 0.5577 (5) | 0.3250 (4) | 0.4493 (3) | 0.0527 (10) | |
H14A | 0.6421 | 0.3332 | 0.3783 | 0.079* | |
H14B | 0.4659 | 0.3654 | 0.4363 | 0.079* | |
H14C | 0.5351 | 0.2420 | 0.4645 | 0.079* | |
C15 | −0.3099 (4) | 0.1315 (3) | 0.7885 (3) | 0.0438 (8) | |
C16 | −0.1790 (4) | 0.1192 (3) | 0.5805 (3) | 0.0368 (7) | |
C17 | −0.0779 (4) | 0.0951 (3) | 0.3824 (3) | 0.0419 (8) | |
C18 | 0.0247 (5) | 0.1125 (4) | 0.2694 (3) | 0.0483 (9) | |
C19 | −0.0073 (6) | 0.0521 (4) | 0.1727 (4) | 0.0610 (11) | |
H19 | 0.0592 | 0.0612 | 0.0961 | 0.073* | |
C20 | −0.1380 (6) | −0.0232 (4) | 0.1863 (4) | 0.0666 (13) | |
H20 | −0.1540 | −0.0643 | 0.1190 | 0.080* | |
C21 | −0.2413 (6) | −0.0372 (4) | 0.2956 (4) | 0.0571 (10) | |
H21 | −0.3288 | −0.0855 | 0.3022 | 0.069* | |
C22 | −0.2155 (4) | 0.0201 (3) | 0.3953 (3) | 0.0421 (8) | |
C23 | 0.1660 (5) | 0.1912 (4) | 0.2562 (4) | 0.0605 (11) | |
H23A | 0.2214 | 0.1941 | 0.1723 | 0.091* | |
H23B | 0.2341 | 0.1596 | 0.3041 | 0.091* | |
H23C | 0.1326 | 0.2703 | 0.2839 | 0.091* | |
Cu1 | −0.01827 (5) | 0.25860 (4) | 0.74480 (4) | 0.03643 (13) | |
N1 | 0.3433 (3) | 0.3479 (3) | 0.6910 (2) | 0.0365 (6) | |
N2 | 0.1146 (3) | 0.3345 (3) | 0.8466 (3) | 0.0417 (7) | |
N3 | −0.1616 (3) | 0.2428 (3) | 0.9016 (2) | 0.0372 (6) | |
N4 | −0.1861 (3) | 0.1609 (3) | 0.6968 (2) | 0.0376 (6) | |
N5 | −0.0615 (4) | 0.1497 (3) | 0.4893 (3) | 0.0394 (7) | |
O1 | 0.0971 (3) | 0.3940 (3) | 1.0469 (2) | 0.0522 (7) | |
O2 | −0.4214 (3) | 0.0679 (3) | 0.7841 (3) | 0.0606 (8) | |
O3 | 0.1087 (3) | 0.2991 (3) | 0.5876 (2) | 0.0499 (6) | |
H31 | 0.2146 | 0.2947 | 0.5929 | 0.075* | |
H32 | 0.0916 | 0.2637 | 0.5369 | 0.075* | |
S1 | 0.38532 (11) | 0.42812 (9) | 0.89733 (8) | 0.0449 (2) | |
S2 | −0.31932 (12) | 0.02247 (9) | 0.54483 (9) | 0.0484 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0372 (18) | 0.047 (2) | 0.0307 (16) | 0.0006 (15) | −0.0052 (14) | 0.0005 (14) |
C2 | 0.044 (2) | 0.060 (2) | 0.0302 (17) | −0.0006 (17) | −0.0005 (15) | −0.0007 (16) |
C3 | 0.040 (2) | 0.081 (3) | 0.043 (2) | −0.009 (2) | 0.0018 (16) | −0.001 (2) |
C4 | 0.0347 (19) | 0.066 (3) | 0.045 (2) | −0.0139 (17) | −0.0079 (16) | 0.0047 (18) |
C5 | 0.0371 (18) | 0.048 (2) | 0.0332 (17) | −0.0098 (15) | −0.0103 (14) | 0.0054 (15) |
C6 | 0.0332 (17) | 0.047 (2) | 0.0329 (17) | 0.0020 (14) | −0.0049 (14) | −0.0047 (14) |
C7 | 0.0317 (17) | 0.0371 (17) | 0.0358 (17) | −0.0095 (13) | −0.0064 (13) | 0.0008 (14) |
C8 | 0.0285 (16) | 0.0345 (17) | 0.0428 (18) | 0.0003 (13) | −0.0111 (14) | 0.0029 (14) |
C9 | 0.056 (2) | 0.0320 (17) | 0.046 (2) | −0.0066 (16) | 0.0029 (17) | 0.0137 (15) |
C10 | 0.042 (2) | 0.040 (2) | 0.068 (3) | −0.0072 (16) | 0.0091 (19) | 0.0090 (18) |
C11 | 0.0291 (19) | 0.060 (2) | 0.079 (3) | −0.0061 (17) | −0.0066 (19) | −0.006 (2) |
C12 | 0.037 (2) | 0.058 (2) | 0.064 (3) | −0.0119 (18) | −0.0098 (18) | 0.007 (2) |
C13 | 0.0280 (17) | 0.0418 (19) | 0.051 (2) | −0.0055 (14) | −0.0080 (15) | 0.0008 (16) |
C14 | 0.049 (2) | 0.062 (2) | 0.040 (2) | −0.0018 (19) | 0.0024 (17) | −0.0003 (18) |
C15 | 0.0309 (18) | 0.056 (2) | 0.045 (2) | −0.0077 (16) | −0.0103 (15) | −0.0076 (17) |
C16 | 0.0373 (18) | 0.0403 (18) | 0.0354 (17) | −0.0025 (14) | −0.0137 (14) | −0.0012 (14) |
C17 | 0.047 (2) | 0.0426 (19) | 0.0383 (18) | 0.0109 (16) | −0.0152 (16) | −0.0084 (15) |
C18 | 0.055 (2) | 0.049 (2) | 0.042 (2) | 0.0138 (18) | −0.0124 (17) | −0.0021 (16) |
C19 | 0.073 (3) | 0.072 (3) | 0.042 (2) | 0.012 (2) | −0.021 (2) | −0.003 (2) |
C20 | 0.097 (4) | 0.068 (3) | 0.045 (2) | 0.017 (3) | −0.039 (3) | −0.019 (2) |
C21 | 0.071 (3) | 0.048 (2) | 0.057 (2) | −0.005 (2) | −0.025 (2) | 0.0006 (19) |
C22 | 0.045 (2) | 0.047 (2) | 0.0390 (18) | 0.0055 (16) | −0.0188 (16) | −0.0020 (16) |
C23 | 0.065 (3) | 0.070 (3) | 0.042 (2) | 0.001 (2) | −0.0025 (19) | 0.011 (2) |
Cu1 | 0.0343 (2) | 0.0468 (3) | 0.0277 (2) | −0.00935 (18) | −0.00593 (16) | −0.00201 (17) |
N1 | 0.0320 (14) | 0.0432 (16) | 0.0342 (14) | −0.0063 (12) | −0.0075 (12) | −0.0002 (12) |
N2 | 0.0325 (15) | 0.0551 (18) | 0.0341 (15) | −0.0109 (13) | −0.0008 (12) | −0.0071 (13) |
N3 | 0.0305 (14) | 0.0509 (17) | 0.0292 (14) | −0.0028 (12) | −0.0048 (11) | −0.0015 (12) |
N4 | 0.0403 (15) | 0.0475 (16) | 0.0286 (14) | −0.0066 (13) | −0.0154 (12) | −0.0012 (12) |
N5 | 0.0450 (17) | 0.0417 (16) | 0.0349 (15) | −0.0011 (13) | −0.0165 (13) | −0.0044 (12) |
O1 | 0.0524 (16) | 0.0689 (18) | 0.0394 (14) | −0.0047 (13) | −0.0188 (12) | −0.0115 (12) |
O2 | 0.0498 (16) | 0.079 (2) | 0.0516 (16) | −0.0310 (15) | −0.0078 (13) | 0.0028 (14) |
O3 | 0.0455 (14) | 0.0666 (17) | 0.0363 (13) | −0.0114 (13) | −0.0065 (11) | 0.0011 (12) |
S1 | 0.0423 (5) | 0.0537 (5) | 0.0396 (5) | −0.0067 (4) | −0.0113 (4) | −0.0104 (4) |
S2 | 0.0474 (5) | 0.0578 (6) | 0.0447 (5) | −0.0121 (4) | −0.0196 (4) | −0.0044 (4) |
Geometric parameters (Å, º) top
C1—N3 | 1.334 (4) | C14—H14B | 0.9600 |
C1—C2 | 1.378 (5) | C14—H14C | 0.9600 |
C1—C6 | 1.511 (5) | C15—O2 | 1.224 (4) |
C2—C3 | 1.409 (5) | C15—N4 | 1.355 (5) |
C2—H2 | 0.9300 | C16—N5 | 1.321 (5) |
C3—C4 | 1.377 (5) | C16—N4 | 1.384 (4) |
C3—H3 | 0.9300 | C16—S2 | 1.761 (3) |
C4—C5 | 1.375 (5) | C17—C18 | 1.393 (5) |
C4—H4 | 0.9300 | C17—N5 | 1.393 (4) |
C5—N3 | 1.329 (4) | C17—C22 | 1.454 (5) |
C5—C15 | 1.519 (5) | C18—C19 | 1.371 (6) |
C6—O1 | 1.241 (4) | C18—C23 | 1.504 (6) |
C6—N2 | 1.361 (4) | C19—C20 | 1.406 (7) |
C7—N1 | 1.306 (4) | C19—H19 | 0.9300 |
C7—N2 | 1.384 (4) | C20—C21 | 1.359 (7) |
C7—S1 | 1.764 (3) | C20—H20 | 0.9300 |
C8—N1 | 1.381 (4) | C21—C22 | 1.363 (5) |
C8—C13 | 1.403 (5) | C21—H21 | 0.9300 |
C8—C9 | 1.404 (5) | C22—S2 | 1.721 (4) |
C9—C10 | 1.400 (6) | C23—H23A | 0.9600 |
C9—C14 | 1.500 (6) | C23—H23B | 0.9600 |
C10—C11 | 1.395 (6) | C23—H23C | 0.9600 |
C10—H10 | 0.9300 | Cu1—O3 | 1.918 (3) |
C11—C12 | 1.379 (6) | Cu1—N3 | 1.925 (3) |
C11—H11 | 0.9300 | Cu1—N2 | 2.012 (3) |
C12—C13 | 1.413 (5) | Cu1—N4 | 2.014 (3) |
C12—H12 | 0.9300 | O3—H31 | 0.9441 |
C13—S1 | 1.742 (4) | O3—H32 | 0.7417 |
C14—H14A | 0.9600 | | |
| | | |
N3—C1—C2 | 118.6 (3) | N5—C16—S2 | 116.3 (2) |
N3—C1—C6 | 114.7 (3) | N4—C16—S2 | 123.3 (3) |
C2—C1—C6 | 126.7 (3) | C18—C17—N5 | 123.8 (4) |
C1—C2—C3 | 118.4 (3) | C18—C17—C22 | 121.2 (3) |
C1—C2—H2 | 120.8 | N5—C17—C22 | 115.0 (3) |
C3—C2—H2 | 120.8 | C19—C18—C17 | 116.8 (4) |
C4—C3—C2 | 120.7 (4) | C19—C18—C23 | 122.2 (4) |
C4—C3—H3 | 119.7 | C17—C18—C23 | 121.0 (3) |
C2—C3—H3 | 119.7 | C18—C19—C20 | 121.8 (4) |
C5—C4—C3 | 118.2 (3) | C18—C19—H19 | 119.1 |
C5—C4—H4 | 120.9 | C20—C19—H19 | 119.1 |
C3—C4—H4 | 120.9 | C21—C20—C19 | 121.6 (4) |
N3—C5—C4 | 119.8 (3) | C21—C20—H20 | 119.2 |
N3—C5—C15 | 113.5 (3) | C19—C20—H20 | 119.2 |
C4—C5—C15 | 126.7 (3) | C20—C21—C22 | 119.3 (4) |
O1—C6—N2 | 127.1 (3) | C20—C21—H21 | 120.3 |
O1—C6—C1 | 121.1 (3) | C22—C21—H21 | 120.3 |
N2—C6—C1 | 111.8 (3) | C21—C22—C17 | 119.2 (4) |
N1—C7—N2 | 121.0 (3) | C21—C22—S2 | 131.7 (3) |
N1—C7—S1 | 115.4 (2) | C17—C22—S2 | 109.0 (2) |
N2—C7—S1 | 123.6 (2) | C18—C23—H23A | 109.5 |
N1—C8—C13 | 116.1 (3) | C18—C23—H23B | 109.5 |
N1—C8—C9 | 123.9 (3) | H23A—C23—H23B | 109.5 |
C13—C8—C9 | 120.0 (3) | C18—C23—H23C | 109.5 |
C10—C9—C8 | 116.7 (4) | H23A—C23—H23C | 109.5 |
C10—C9—C14 | 122.8 (4) | H23B—C23—H23C | 109.5 |
C8—C9—C14 | 120.5 (3) | O3—Cu1—N3 | 170.69 (13) |
C11—C10—C9 | 122.5 (4) | O3—Cu1—N2 | 98.04 (12) |
C11—C10—H10 | 118.7 | N3—Cu1—N2 | 81.61 (11) |
C9—C10—H10 | 118.7 | O3—Cu1—N4 | 100.58 (11) |
C12—C11—C10 | 121.9 (4) | N3—Cu1—N4 | 80.55 (12) |
C12—C11—H11 | 119.1 | N2—Cu1—N4 | 161.09 (12) |
C10—C11—H11 | 119.1 | C7—N1—C8 | 110.6 (3) |
C11—C12—C13 | 115.9 (4) | C6—N2—C7 | 120.4 (3) |
C11—C12—H12 | 122.1 | C6—N2—Cu1 | 114.7 (2) |
C13—C12—H12 | 122.1 | C7—N2—Cu1 | 124.8 (2) |
C8—C13—C12 | 123.0 (3) | C5—N3—C1 | 124.3 (3) |
C8—C13—S1 | 108.9 (2) | C5—N3—Cu1 | 118.7 (2) |
C12—C13—S1 | 128.1 (3) | C1—N3—Cu1 | 117.0 (2) |
C9—C14—H14A | 109.5 | C15—N4—C16 | 119.5 (3) |
C9—C14—H14B | 109.5 | C15—N4—Cu1 | 115.7 (2) |
H14A—C14—H14B | 109.5 | C16—N4—Cu1 | 124.7 (2) |
C9—C14—H14C | 109.5 | C16—N5—C17 | 109.9 (3) |
H14A—C14—H14C | 109.5 | Cu1—O3—H31 | 107.2 |
H14B—C14—H14C | 109.5 | Cu1—O3—H32 | 114.1 |
O2—C15—N4 | 128.2 (3) | H31—O3—H32 | 113.9 |
O2—C15—C5 | 120.2 (3) | C13—S1—C7 | 89.00 (16) |
N4—C15—C5 | 111.5 (3) | C22—S2—C16 | 89.77 (17) |
N5—C16—N4 | 120.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H32···N5 | 0.74 | 2.02 | 2.661 (4) | 145 |
O3—H31···N1 | 0.94 | 1.86 | 2.652 (4) | 140 |
C12—H12···O1i | 0.93 | 2.55 | 3.431 (5) | 157 |
C23—H23B···S2ii | 0.96 | 2.86 | 3.734 (5) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y, −z+1. |