In the title compound, [Cu(C
12H
8N
2)(C
7H
4SO
5)(H
2O)]·C
3H
7NO, the Cu
II atom has a square-pyramidal coordination geometry formed by three O atom and two N atoms. The 1,2-di-4-pyridylethylene ligands function as μ
2-bridging ligands to form a zigzag chain. The 2-sulfonatobenzoate ligands protrude on alternate sides of the chain. Intermolecular O—H
O hydrogen bonds link the chains into a two-dimensional network structure.
Supporting information
CCDC reference: 271857
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.094
- wR factor = 0.170
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT213_ALERT_2_C Atom C7 has ADP max/min Ratio ............. 3.90 prolat
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C13 - C14 ... 1.53 Ang.
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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.
catena-Poly[[µ-1,2-di-4-pyridylethylene-
κ2N,
N'-[aqua(2-sulfonatobenzoato-
κ2O,
O')copper(II)]]
N,
N-dimethylformamide]
top
Crystal data top
[Cu(C12H8N2)(C7H4SO5)(H2O)]·C3H7NO | F(000) = 2216 |
Mr = 537.03 | Dx = 1.579 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2377 reflections |
a = 17.3586 (19) Å | θ = 2.5–21.8° |
b = 9.8854 (11) Å | µ = 1.11 mm−1 |
c = 26.324 (3) Å | T = 298 K |
V = 4517.1 (9) Å3 | Prism, blue |
Z = 8 | 0.20 × 0.17 × 0.15 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4102 independent reflections |
Radiation source: fine-focus sealed tube | 3679 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
φ and ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −19→20 |
Tmin = 0.809, Tmax = 0.851 | k = −11→11 |
22879 measured reflections | l = −28→31 |
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)] = 0.094 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.42 | w = 1/[σ2(Fo2) + (0.0339P)2 + 17.9772P] where P = (Fo2 + 2Fc2)/3 |
4102 reflections | (Δ/σ)max = 0.001 |
310 parameters | Δρmax = 0.64 e Å−3 |
2 restraints | Δρmin = −0.81 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 | |
Cu1 | 0.82253 (4) | 0.33928 (7) | 0.86116 (3) | 0.0179 (2) | |
S1 | 1.00557 (9) | 0.43566 (18) | 0.86391 (6) | 0.0275 (4) | |
O1 | 0.8217 (3) | 0.5373 (4) | 0.85964 (15) | 0.0258 (10) | |
O2 | 0.8527 (3) | 0.7485 (5) | 0.84165 (19) | 0.0393 (12) | |
O3 | 0.9517 (2) | 0.3240 (4) | 0.87282 (16) | 0.0277 (10) | |
O4 | 0.9936 (3) | 0.5485 (5) | 0.89786 (17) | 0.0381 (12) | |
O5 | 1.0843 (3) | 0.3909 (6) | 0.86131 (19) | 0.0421 (13) | |
O6 | 0.8225 (3) | 0.1377 (4) | 0.86305 (16) | 0.0278 (10) | |
H6A | 0.8478 | 0.1117 | 0.8875 | 0.042* | |
H6B | 0.7774 | 0.1138 | 0.8648 | 0.042* | |
O7 | 0.8788 (4) | 1.0325 (6) | −0.0525 (2) | 0.069 (2) | |
N1 | 0.8035 (3) | 0.3468 (5) | 0.93674 (18) | 0.0220 (12) | |
N2 | 0.8087 (3) | 0.1734 (5) | 1.28618 (17) | 0.0184 (11) | |
N3 | 0.9263 (4) | 0.8753 (6) | 0.0009 (2) | 0.0410 (16) | |
C1 | 0.8507 (4) | 0.4210 (7) | 0.9654 (2) | 0.0241 (14) | |
H1 | 0.8831 | 0.4830 | 0.9496 | 0.029* | |
C2 | 0.8534 (4) | 0.4095 (7) | 1.0176 (2) | 0.0269 (15) | |
H2 | 0.8870 | 0.4632 | 1.0363 | 0.032* | |
C3 | 0.8057 (4) | 0.3173 (7) | 1.0423 (2) | 0.0234 (14) | |
C4 | 0.7549 (4) | 0.2448 (7) | 1.0124 (2) | 0.0278 (15) | |
H4 | 0.7203 | 0.1849 | 1.0273 | 0.033* | |
C5 | 0.7560 (4) | 0.2616 (7) | 0.9603 (2) | 0.0256 (15) | |
H5 | 0.7218 | 0.2111 | 0.9408 | 0.031* | |
C6 | 0.8138 (4) | 0.3005 (7) | 1.0972 (2) | 0.0311 (16) | |
H6 | 0.8502 | 0.3552 | 1.1130 | 0.037* | |
C7 | 0.7755 (4) | 0.2169 (7) | 1.1268 (2) | 0.0282 (16) | |
H7 | 0.7373 | 0.1643 | 1.1119 | 0.034* | |
C8 | 0.7886 (4) | 0.2006 (6) | 1.1814 (2) | 0.0225 (14) | |
C9 | 0.7413 (4) | 0.1178 (6) | 1.2098 (2) | 0.0209 (14) | |
H9 | 0.7019 | 0.0695 | 1.1942 | 0.025* | |
C10 | 0.7527 (4) | 0.1068 (6) | 1.2617 (2) | 0.0215 (14) | |
H10 | 0.7201 | 0.0510 | 1.2803 | 0.026* | |
C11 | 0.8559 (4) | 0.2495 (7) | 1.2585 (2) | 0.0250 (14) | |
H11 | 0.8960 | 0.2942 | 1.2749 | 0.030* | |
C12 | 0.8485 (4) | 0.2654 (7) | 1.2071 (2) | 0.0279 (15) | |
H12 | 0.8832 | 0.3192 | 1.1894 | 0.034* | |
C13 | 0.8626 (4) | 0.6281 (6) | 0.8357 (2) | 0.0201 (13) | |
C14 | 0.9173 (4) | 0.5780 (6) | 0.7944 (2) | 0.0247 (15) | |
C15 | 0.9807 (4) | 0.4951 (6) | 0.8019 (2) | 0.0219 (14) | |
C16 | 1.0242 (4) | 0.4525 (7) | 0.7606 (2) | 0.0310 (16) | |
H16 | 1.0667 | 0.3970 | 0.7659 | 0.037* | |
C17 | 1.0055 (5) | 0.4907 (8) | 0.7122 (3) | 0.0391 (19) | |
H17 | 1.0348 | 0.4601 | 0.6850 | 0.047* | |
C18 | 0.9438 (5) | 0.5739 (8) | 0.7040 (3) | 0.040 (2) | |
H18 | 0.9314 | 0.6019 | 0.6713 | 0.048* | |
C19 | 0.9001 (4) | 0.6160 (7) | 0.7451 (3) | 0.0335 (17) | |
H19 | 0.8577 | 0.6716 | 0.7393 | 0.040* | |
C20 | 0.9053 (6) | 0.9470 (10) | 0.0464 (3) | 0.066 (3) | |
H20A | 0.8861 | 1.0350 | 0.0376 | 0.098* | |
H20B | 0.9498 | 0.9564 | 0.0678 | 0.098* | |
H20C | 0.8661 | 0.8974 | 0.0641 | 0.098* | |
C21 | 0.9677 (6) | 0.7490 (9) | 0.0065 (4) | 0.076 (3) | |
H21A | 1.0182 | 0.7666 | 0.0198 | 0.113* | |
H21B | 0.9721 | 0.7055 | −0.0260 | 0.113* | |
H21C | 0.9402 | 0.6910 | 0.0295 | 0.113* | |
C22 | 0.9097 (5) | 0.9246 (9) | −0.0446 (3) | 0.048 (2) | |
H22 | 0.9229 | 0.8724 | −0.0727 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0227 (4) | 0.0212 (4) | 0.0100 (4) | 0.0004 (3) | −0.0006 (3) | 0.0002 (3) |
S1 | 0.0189 (8) | 0.0389 (9) | 0.0246 (8) | −0.0022 (7) | −0.0028 (7) | 0.0016 (8) |
O1 | 0.031 (2) | 0.025 (2) | 0.021 (2) | 0.003 (2) | 0.002 (2) | 0.0008 (19) |
O2 | 0.051 (3) | 0.022 (3) | 0.045 (3) | 0.002 (2) | 0.010 (2) | −0.002 (2) |
O3 | 0.026 (2) | 0.032 (3) | 0.025 (2) | −0.001 (2) | −0.0033 (19) | 0.007 (2) |
O4 | 0.037 (3) | 0.050 (3) | 0.027 (3) | −0.010 (3) | −0.003 (2) | −0.006 (2) |
O5 | 0.019 (2) | 0.064 (3) | 0.043 (3) | 0.002 (2) | −0.003 (2) | 0.008 (3) |
O6 | 0.029 (2) | 0.025 (2) | 0.029 (2) | −0.003 (2) | −0.006 (2) | 0.002 (2) |
O7 | 0.084 (5) | 0.056 (4) | 0.067 (4) | 0.010 (4) | −0.035 (4) | 0.024 (3) |
N1 | 0.023 (3) | 0.031 (3) | 0.012 (2) | 0.001 (2) | 0.002 (2) | 0.004 (2) |
N2 | 0.018 (3) | 0.023 (3) | 0.014 (2) | −0.001 (2) | −0.001 (2) | 0.000 (2) |
N3 | 0.044 (4) | 0.042 (4) | 0.037 (4) | 0.004 (3) | −0.005 (3) | 0.013 (3) |
C1 | 0.028 (4) | 0.029 (4) | 0.015 (3) | −0.005 (3) | −0.001 (3) | 0.002 (3) |
C2 | 0.035 (4) | 0.031 (4) | 0.015 (3) | −0.004 (3) | −0.004 (3) | −0.002 (3) |
C3 | 0.022 (4) | 0.031 (4) | 0.017 (3) | −0.001 (3) | 0.000 (3) | 0.002 (3) |
C4 | 0.025 (4) | 0.041 (4) | 0.017 (3) | −0.007 (3) | 0.002 (3) | 0.007 (3) |
C5 | 0.023 (3) | 0.038 (4) | 0.016 (3) | −0.004 (3) | 0.001 (3) | 0.002 (3) |
C6 | 0.034 (4) | 0.040 (4) | 0.020 (3) | −0.007 (3) | −0.006 (3) | −0.001 (3) |
C7 | 0.030 (4) | 0.050 (4) | 0.004 (3) | −0.008 (3) | −0.003 (2) | 0.004 (3) |
C8 | 0.028 (4) | 0.021 (3) | 0.018 (3) | 0.001 (3) | −0.004 (3) | 0.001 (3) |
C9 | 0.020 (3) | 0.023 (3) | 0.019 (3) | −0.001 (3) | −0.006 (3) | −0.002 (3) |
C10 | 0.021 (3) | 0.025 (3) | 0.018 (3) | −0.006 (3) | 0.006 (3) | 0.004 (3) |
C11 | 0.022 (3) | 0.032 (4) | 0.022 (3) | −0.005 (3) | −0.003 (3) | −0.001 (3) |
C12 | 0.032 (4) | 0.031 (4) | 0.021 (3) | −0.014 (3) | 0.001 (3) | 0.007 (3) |
C13 | 0.024 (3) | 0.017 (3) | 0.020 (3) | 0.003 (3) | −0.002 (3) | 0.003 (3) |
C14 | 0.023 (4) | 0.027 (4) | 0.024 (3) | −0.008 (3) | 0.002 (3) | 0.006 (3) |
C15 | 0.019 (3) | 0.027 (3) | 0.020 (3) | −0.012 (3) | 0.003 (3) | 0.001 (3) |
C16 | 0.026 (4) | 0.037 (4) | 0.031 (4) | −0.008 (3) | 0.006 (3) | −0.002 (3) |
C17 | 0.049 (5) | 0.045 (5) | 0.024 (4) | −0.009 (4) | 0.017 (3) | −0.009 (3) |
C18 | 0.060 (6) | 0.041 (5) | 0.020 (4) | −0.012 (4) | 0.001 (3) | 0.009 (3) |
C19 | 0.039 (4) | 0.030 (4) | 0.032 (4) | 0.000 (3) | −0.002 (3) | 0.008 (3) |
C20 | 0.062 (6) | 0.077 (7) | 0.059 (6) | −0.013 (5) | 0.004 (5) | −0.001 (5) |
C21 | 0.083 (8) | 0.045 (6) | 0.099 (8) | 0.018 (5) | −0.016 (6) | 0.010 (6) |
C22 | 0.044 (5) | 0.059 (6) | 0.042 (5) | −0.011 (4) | −0.011 (4) | 0.007 (4) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.958 (4) | C6—C7 | 1.316 (9) |
Cu1—N2i | 1.992 (5) | C6—H6 | 0.9300 |
Cu1—O6 | 1.993 (4) | C7—C8 | 1.465 (8) |
Cu1—N1 | 2.018 (5) | C7—H7 | 0.9300 |
Cu1—O3 | 2.268 (4) | C8—C9 | 1.380 (9) |
S1—O5 | 1.438 (5) | C8—C12 | 1.395 (9) |
S1—O4 | 1.444 (5) | C9—C10 | 1.385 (8) |
S1—O3 | 1.466 (5) | C9—H9 | 0.9300 |
S1—C15 | 1.787 (6) | C10—H10 | 0.9300 |
O1—C13 | 1.307 (7) | C11—C12 | 1.367 (9) |
O2—C13 | 1.212 (7) | C11—H11 | 0.9300 |
O6—H6A | 0.8200 | C12—H12 | 0.9300 |
O6—H6B | 0.8189 | C13—C14 | 1.525 (9) |
O7—C22 | 1.212 (10) | C14—C19 | 1.385 (9) |
N1—C5 | 1.333 (8) | C14—C15 | 1.387 (9) |
N1—C1 | 1.334 (8) | C15—C16 | 1.390 (9) |
N2—C11 | 1.331 (8) | C16—C17 | 1.365 (10) |
N2—C10 | 1.339 (8) | C16—H16 | 0.9300 |
N2—Cu1ii | 1.992 (5) | C17—C18 | 1.368 (11) |
N3—C22 | 1.325 (9) | C17—H17 | 0.9300 |
N3—C20 | 1.439 (10) | C18—C19 | 1.384 (10) |
N3—C21 | 1.449 (10) | C18—H18 | 0.9300 |
C1—C2 | 1.380 (8) | C19—H19 | 0.9300 |
C1—H1 | 0.9300 | C20—H20A | 0.9600 |
C2—C3 | 1.392 (9) | C20—H20B | 0.9600 |
C2—H2 | 0.9300 | C20—H20C | 0.9600 |
C3—C4 | 1.382 (9) | C21—H21A | 0.9600 |
C3—C6 | 1.461 (8) | C21—H21B | 0.9600 |
C4—C5 | 1.381 (8) | C21—H21C | 0.9600 |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—H5 | 0.9300 | | |
| | | |
O1—Cu1—N2i | 92.38 (19) | C9—C8—C12 | 116.9 (6) |
O1—Cu1—O6 | 179.47 (19) | C9—C8—C7 | 120.3 (6) |
N2i—Cu1—O6 | 87.82 (19) | C12—C8—C7 | 122.8 (6) |
O1—Cu1—N1 | 88.98 (19) | C8—C9—C10 | 119.7 (6) |
N2i—Cu1—N1 | 163.59 (19) | C8—C9—H9 | 120.1 |
O6—Cu1—N1 | 90.7 (2) | C10—C9—H9 | 120.1 |
O1—Cu1—O3 | 94.43 (18) | N2—C10—C9 | 122.7 (6) |
N2i—Cu1—O3 | 104.44 (17) | N2—C10—H10 | 118.7 |
O6—Cu1—O3 | 86.00 (17) | C9—C10—H10 | 118.7 |
N1—Cu1—O3 | 91.76 (18) | N2—C11—C12 | 123.3 (6) |
O5—S1—O4 | 113.8 (3) | N2—C11—H11 | 118.4 |
O5—S1—O3 | 112.5 (3) | C12—C11—H11 | 118.4 |
O4—S1—O3 | 113.0 (3) | C11—C12—C8 | 119.8 (6) |
O5—S1—C15 | 106.7 (3) | C11—C12—H12 | 120.1 |
O4—S1—C15 | 106.1 (3) | C8—C12—H12 | 120.1 |
O3—S1—C15 | 103.9 (3) | O2—C13—O1 | 122.3 (6) |
C13—O1—Cu1 | 133.8 (4) | O2—C13—C14 | 120.0 (6) |
S1—O3—Cu1 | 124.0 (3) | O1—C13—C14 | 117.3 (5) |
Cu1—O6—H6A | 109.5 | C19—C14—C15 | 117.7 (6) |
Cu1—O6—H6B | 106.9 | C19—C14—C13 | 116.5 (6) |
H6A—O6—H6B | 112.2 | C15—C14—C13 | 125.8 (5) |
C5—N1—C1 | 117.7 (5) | C14—C15—C16 | 119.9 (6) |
C5—N1—Cu1 | 122.5 (4) | C14—C15—S1 | 121.1 (5) |
C1—N1—Cu1 | 118.5 (4) | C16—C15—S1 | 119.0 (5) |
C11—N2—C10 | 117.5 (5) | C17—C16—C15 | 121.2 (7) |
C11—N2—Cu1ii | 120.3 (4) | C17—C16—H16 | 119.4 |
C10—N2—Cu1ii | 122.2 (4) | C15—C16—H16 | 119.4 |
C22—N3—C20 | 121.1 (7) | C16—C17—C18 | 119.9 (7) |
C22—N3—C21 | 121.2 (8) | C16—C17—H17 | 120.0 |
C20—N3—C21 | 117.7 (7) | C18—C17—H17 | 120.0 |
N1—C1—C2 | 122.6 (6) | C17—C18—C19 | 119.2 (7) |
N1—C1—H1 | 118.7 | C17—C18—H18 | 120.4 |
C2—C1—H1 | 118.7 | C19—C18—H18 | 120.4 |
C1—C2—C3 | 119.9 (6) | C18—C19—C14 | 122.1 (7) |
C1—C2—H2 | 120.0 | C18—C19—H19 | 118.9 |
C3—C2—H2 | 120.0 | C14—C19—H19 | 118.9 |
C4—C3—C2 | 116.9 (6) | N3—C20—H20A | 109.5 |
C4—C3—C6 | 124.4 (6) | N3—C20—H20B | 109.5 |
C2—C3—C6 | 118.6 (6) | H20A—C20—H20B | 109.5 |
C5—C4—C3 | 119.6 (6) | N3—C20—H20C | 109.5 |
C5—C4—H4 | 120.2 | H20A—C20—H20C | 109.5 |
C3—C4—H4 | 120.2 | H20B—C20—H20C | 109.5 |
N1—C5—C4 | 123.1 (6) | N3—C21—H21A | 109.5 |
N1—C5—H5 | 118.4 | N3—C21—H21B | 109.5 |
C4—C5—H5 | 118.4 | H21A—C21—H21B | 109.5 |
C7—C6—C3 | 127.5 (6) | N3—C21—H21C | 109.5 |
C7—C6—H6 | 116.3 | H21A—C21—H21C | 109.5 |
C3—C6—H6 | 116.3 | H21B—C21—H21C | 109.5 |
C6—C7—C8 | 124.9 (6) | O7—C22—N3 | 125.1 (9) |
C6—C7—H7 | 117.6 | O7—C22—H22 | 117.5 |
C8—C7—H7 | 117.6 | N3—C22—H22 | 117.5 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6B···O1iii | 0.82 | 1.88 | 2.693 (6) | 170 |
O6—H6A···O7iv | 0.82 | 1.84 | 2.642 (7) | 164 |
Symmetry codes: (iii) −x+3/2, y−1/2, z; (iv) x, y−1, z+1. |