Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051963/hb2595sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051963/hb2595Isup2.hkl |
CCDC reference: 667225
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.093
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O2
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.05 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 5 Informative message, check
A mixture of CuCl2.2H2O (0.5 mmol), H2L (0.5 mmol), Pyphen (0.5 mmol), and H2O (500 mmol) was adjusted to pH = 5.5 by addition of aqueous NaOH solution, and heated at 453 K for six days. After the mixture was slowly cooled to room temperature, blue blocks of (I) resulted.
The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C). The water H-atoms were located in a difference Fourier map, and their positions were freely refined with Uiso(H) = 1.2Ueq(O).
Studies on metal dicarboxylato complexes with heteroaromatic N-donor chelating ligands are of current interest (Chen & Liu, 2002). Pyrazino[2,3-f][1,10]phenanthroline (Pyphen) as a new phen derivative possesses an extended aromatic system. We selected 4,4'-oxybis(benzoic acid) (H2L) as a linker and Pyphen as a secondary chelating ligand, and in combination with Cu2+ ions, generaed the new coordination polymer, [Cu(L)(Pyphen)].H2O, (I), which is reported here.
In compound (I) the CuII atom is four-coordinated by two Pyphen N atoms and two carboxylate O atoms, and exhibits a distorted square-planar coordination sphere (Table 1, Fig. 1). The L ligands link the CuII atoms to generate a distinctive helical chain structure (Fig. 2). The Pyphen ligands are attached on both sides of the chains. The neighbouring chains are linked through π-π interactions between Pyphen ligands with a π-π stacking distance of ca 3.44 Å, resulting in a two-dimensional supramolecular structure (Fig. 3). Finally, O—H···O hydrogen bonds involving the water molecule and carboxylate O atom acceptors (Table 2) complete the structure of (I).
For the crystal structure of the zinc 4,4'-oxybis(benzoate) adduct with bis(3-pyridylmethylene)-p-phenylenediamine, see Kim et al. (2005). For the crystal structure of the acid itself, see Dey & Desiraju (2005). For background, see: Chen & Liu (2002).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Cu(C14H8O5)(C14H8N4)]·H2O | F(000) = 1164 |
Mr = 570.00 | Dx = 1.614 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 16143 reflections |
a = 5.8092 (12) Å | θ = 3.0–27.5° |
b = 14.635 (3) Å | µ = 0.99 mm−1 |
c = 27.600 (6) Å | T = 293 K |
β = 91.87 (3)° | Block, blue |
V = 2345.2 (8) Å3 | 0.22 × 0.19 × 0.18 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5350 independent reflections |
Radiation source: rotor target | 4136 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −6→7 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→18 |
Tmin = 0.801, Tmax = 0.837 | l = −35→35 |
21478 measured reflections |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0434P)2 + 1.748P] where P = (Fo2 + 2Fc2)/3 |
5350 reflections | (Δ/σ)max < 0.001 |
358 parameters | Δρmax = 0.38 e Å−3 |
3 restraints | Δρmin = −0.28 e Å−3 |
[Cu(C14H8O5)(C14H8N4)]·H2O | V = 2345.2 (8) Å3 |
Mr = 570.00 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.8092 (12) Å | µ = 0.99 mm−1 |
b = 14.635 (3) Å | T = 293 K |
c = 27.600 (6) Å | 0.22 × 0.19 × 0.18 mm |
β = 91.87 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5350 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4136 reflections with I > 2σ(I) |
Tmin = 0.801, Tmax = 0.837 | Rint = 0.042 |
21478 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 3 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | Δρmax = 0.38 e Å−3 |
5350 reflections | Δρmin = −0.28 e Å−3 |
358 parameters |
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 | ||
C1 | 0.4790 (4) | 0.12450 (17) | −0.00903 (8) | 0.0361 (5) | |
H1 | 0.4997 | 0.1093 | 0.0235 | 0.043* | |
C2 | 0.6371 (4) | 0.09219 (17) | −0.04221 (9) | 0.0388 (5) | |
H2 | 0.7596 | 0.0554 | −0.0318 | 0.047* | |
C3 | 0.6096 (4) | 0.11542 (17) | −0.09034 (9) | 0.0388 (5) | |
H3 | 0.7119 | 0.0938 | −0.1129 | 0.047* | |
C4 | 0.4259 (4) | 0.17202 (15) | −0.10503 (7) | 0.0315 (5) | |
C5 | 0.2744 (4) | 0.20030 (15) | −0.06972 (7) | 0.0283 (4) | |
C6 | 0.0836 (4) | 0.25939 (15) | −0.08175 (7) | 0.0281 (4) | |
C7 | −0.2261 (4) | 0.33950 (17) | −0.05277 (8) | 0.0370 (5) | |
H7 | −0.3182 | 0.3559 | −0.0272 | 0.044* | |
C8 | −0.2754 (4) | 0.37489 (18) | −0.09876 (9) | 0.0423 (6) | |
H8 | −0.3974 | 0.4154 | −0.1035 | 0.051* | |
C9 | −0.1446 (4) | 0.35019 (17) | −0.13711 (8) | 0.0394 (5) | |
H9 | −0.1790 | 0.3726 | −0.1680 | 0.047* | |
C10 | 0.0412 (4) | 0.29078 (15) | −0.12899 (7) | 0.0321 (5) | |
C11 | 0.1980 (4) | 0.26118 (16) | −0.16618 (7) | 0.0359 (5) | |
C12 | 0.3847 (4) | 0.20461 (16) | −0.15441 (7) | 0.0357 (5) | |
C13 | 0.4951 (6) | 0.2109 (2) | −0.23221 (10) | 0.0637 (9) | |
H13 | 0.5960 | 0.1955 | −0.2564 | 0.076* | |
C14 | 0.3086 (6) | 0.2657 (2) | −0.24421 (9) | 0.0639 (9) | |
H14 | 0.2875 | 0.2849 | −0.2762 | 0.077* | |
C15 | −0.1443 (4) | 0.3508 (2) | 0.07387 (8) | 0.0434 (6) | |
C16 | −0.2925 (4) | 0.38171 (17) | 0.11430 (7) | 0.0349 (5) | |
C17 | −0.2267 (4) | 0.45479 (18) | 0.14310 (9) | 0.0425 (6) | |
H17 | −0.0891 | 0.4848 | 0.1374 | 0.051* | |
C18 | −0.3623 (4) | 0.48415 (17) | 0.18046 (8) | 0.0421 (6) | |
H18 | −0.3158 | 0.5330 | 0.2000 | 0.051* | |
C19 | −0.5678 (4) | 0.43965 (17) | 0.18814 (7) | 0.0348 (5) | |
C20 | −0.6358 (4) | 0.36678 (18) | 0.15973 (8) | 0.0399 (6) | |
H20 | −0.7745 | 0.3374 | 0.1652 | 0.048* | |
C21 | −0.4979 (4) | 0.33725 (18) | 0.12300 (8) | 0.0397 (5) | |
H21 | −0.5429 | 0.2874 | 0.1041 | 0.048* | |
C22 | −0.4232 (4) | 0.51097 (18) | 0.33805 (8) | 0.0385 (5) | |
H22 | −0.2904 | 0.4936 | 0.3554 | 0.046* | |
C23 | −0.5780 (4) | 0.56945 (16) | 0.35915 (7) | 0.0320 (5) | |
C24 | −0.5366 (4) | 0.60147 (17) | 0.41048 (7) | 0.0363 (5) | |
C25 | −0.7731 (4) | 0.59633 (18) | 0.33245 (8) | 0.0407 (6) | |
H25 | −0.8773 | 0.6364 | 0.3460 | 0.049* | |
C26 | −0.8138 (4) | 0.5641 (2) | 0.28603 (8) | 0.0431 (6) | |
H26 | −0.9448 | 0.5823 | 0.2683 | 0.052* | |
C27 | −0.6593 (4) | 0.50457 (17) | 0.26594 (7) | 0.0356 (5) | |
C28 | −0.4628 (4) | 0.47786 (18) | 0.29149 (8) | 0.0414 (6) | |
H28 | −0.3584 | 0.4382 | 0.2777 | 0.050* | |
N1 | 0.3008 (3) | 0.17603 (13) | −0.02252 (6) | 0.0306 (4) | |
N2 | −0.0514 (3) | 0.28303 (13) | −0.04452 (6) | 0.0303 (4) | |
N3 | 0.5371 (4) | 0.17933 (17) | −0.18796 (7) | 0.0514 (6) | |
N4 | 0.1586 (4) | 0.29205 (16) | −0.21202 (7) | 0.0508 (6) | |
O1 | −0.2016 (3) | 0.27603 (14) | 0.05340 (6) | 0.0499 (5) | |
O2 | 0.0231 (4) | 0.3962 (2) | 0.06309 (8) | 0.0843 (9) | |
O1W | 0.3162 (5) | 0.4364 (2) | −0.01300 (11) | 0.0905 (9) | |
HW11 | 0.314 (9) | 0.413 (3) | 0.0136 (15) | 0.136* | |
HW12 | 0.198 (6) | 0.474 (3) | −0.0176 (17) | 0.136* | |
O3 | −0.7268 (3) | 0.47003 (14) | 0.22092 (6) | 0.0481 (5) | |
O4 | −0.3897 (3) | 0.56465 (15) | 0.43667 (6) | 0.0551 (5) | |
O5 | −0.6671 (3) | 0.66682 (14) | 0.42371 (6) | 0.0467 (4) | |
Cu1 | 0.05118 (5) | 0.22577 (2) | 0.018498 (8) | 0.03191 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0395 (12) | 0.0371 (13) | 0.0316 (11) | −0.0004 (10) | −0.0021 (9) | 0.0035 (9) |
C2 | 0.0370 (12) | 0.0345 (13) | 0.0449 (13) | 0.0059 (10) | −0.0003 (10) | 0.0003 (10) |
C3 | 0.0383 (12) | 0.0361 (13) | 0.0425 (12) | 0.0002 (10) | 0.0084 (10) | −0.0072 (10) |
C4 | 0.0376 (11) | 0.0308 (11) | 0.0263 (10) | −0.0045 (9) | 0.0038 (9) | −0.0050 (8) |
C5 | 0.0339 (11) | 0.0278 (11) | 0.0233 (9) | −0.0033 (8) | 0.0025 (8) | −0.0007 (8) |
C6 | 0.0341 (11) | 0.0287 (11) | 0.0216 (9) | −0.0035 (9) | 0.0021 (8) | −0.0007 (8) |
C7 | 0.0380 (12) | 0.0388 (13) | 0.0343 (11) | 0.0037 (10) | 0.0056 (9) | −0.0010 (10) |
C8 | 0.0442 (13) | 0.0402 (14) | 0.0421 (13) | 0.0059 (11) | −0.0026 (11) | 0.0051 (11) |
C9 | 0.0471 (13) | 0.0400 (14) | 0.0308 (11) | −0.0028 (11) | −0.0044 (10) | 0.0074 (10) |
C10 | 0.0395 (12) | 0.0312 (12) | 0.0255 (10) | −0.0032 (9) | −0.0003 (9) | 0.0012 (8) |
C11 | 0.0532 (14) | 0.0329 (12) | 0.0217 (9) | −0.0064 (11) | 0.0049 (9) | 0.0001 (9) |
C12 | 0.0494 (14) | 0.0339 (13) | 0.0243 (10) | −0.0074 (10) | 0.0096 (9) | −0.0057 (8) |
C13 | 0.097 (2) | 0.064 (2) | 0.0325 (13) | 0.0064 (18) | 0.0293 (15) | −0.0031 (13) |
C14 | 0.108 (3) | 0.0623 (19) | 0.0226 (11) | 0.0064 (19) | 0.0156 (14) | 0.0029 (12) |
C15 | 0.0414 (13) | 0.0634 (18) | 0.0258 (11) | 0.0038 (12) | 0.0059 (10) | 0.0018 (11) |
C16 | 0.0395 (12) | 0.0404 (13) | 0.0250 (10) | −0.0003 (10) | 0.0050 (9) | −0.0009 (9) |
C17 | 0.0419 (13) | 0.0452 (15) | 0.0407 (12) | −0.0099 (11) | 0.0058 (10) | −0.0019 (11) |
C18 | 0.0521 (14) | 0.0376 (14) | 0.0364 (12) | −0.0048 (11) | −0.0015 (11) | −0.0111 (10) |
C19 | 0.0397 (12) | 0.0425 (13) | 0.0222 (9) | 0.0065 (10) | −0.0001 (9) | −0.0056 (9) |
C20 | 0.0406 (13) | 0.0511 (15) | 0.0284 (10) | −0.0091 (11) | 0.0066 (9) | −0.0080 (10) |
C21 | 0.0456 (13) | 0.0446 (14) | 0.0292 (11) | −0.0083 (11) | 0.0061 (10) | −0.0109 (10) |
C22 | 0.0406 (12) | 0.0445 (14) | 0.0299 (10) | 0.0088 (11) | −0.0048 (9) | −0.0011 (10) |
C23 | 0.0386 (12) | 0.0343 (12) | 0.0231 (9) | −0.0011 (9) | −0.0001 (8) | −0.0001 (8) |
C24 | 0.0416 (12) | 0.0445 (14) | 0.0227 (10) | −0.0087 (11) | 0.0007 (9) | −0.0023 (9) |
C25 | 0.0433 (13) | 0.0492 (15) | 0.0296 (11) | 0.0140 (11) | −0.0002 (10) | −0.0095 (10) |
C26 | 0.0400 (13) | 0.0599 (17) | 0.0291 (11) | 0.0158 (12) | −0.0051 (10) | −0.0094 (11) |
C27 | 0.0388 (12) | 0.0439 (14) | 0.0240 (9) | 0.0037 (10) | −0.0005 (9) | −0.0085 (9) |
C28 | 0.0439 (13) | 0.0462 (15) | 0.0338 (11) | 0.0140 (11) | −0.0010 (10) | −0.0083 (10) |
N1 | 0.0348 (9) | 0.0332 (10) | 0.0237 (8) | 0.0000 (8) | −0.0002 (7) | 0.0025 (7) |
N2 | 0.0350 (9) | 0.0322 (10) | 0.0240 (8) | 0.0004 (8) | 0.0041 (7) | 0.0006 (7) |
N3 | 0.0666 (15) | 0.0540 (14) | 0.0349 (11) | 0.0030 (12) | 0.0217 (10) | −0.0061 (10) |
N4 | 0.0791 (17) | 0.0493 (14) | 0.0242 (9) | 0.0031 (12) | 0.0051 (10) | 0.0051 (9) |
O1 | 0.0619 (12) | 0.0558 (12) | 0.0328 (8) | 0.0094 (10) | 0.0170 (8) | −0.0032 (8) |
O2 | 0.0653 (14) | 0.134 (2) | 0.0556 (12) | −0.0439 (15) | 0.0313 (11) | −0.0251 (14) |
O1W | 0.0792 (18) | 0.097 (2) | 0.098 (2) | −0.0191 (15) | 0.0410 (16) | −0.0156 (16) |
O3 | 0.0406 (9) | 0.0732 (13) | 0.0304 (8) | 0.0079 (9) | 0.0001 (7) | −0.0229 (8) |
O4 | 0.0686 (12) | 0.0633 (13) | 0.0323 (9) | 0.0052 (10) | −0.0163 (9) | −0.0004 (9) |
O5 | 0.0503 (10) | 0.0640 (12) | 0.0260 (8) | 0.0021 (9) | 0.0041 (7) | −0.0141 (8) |
Cu1 | 0.03902 (16) | 0.03777 (16) | 0.01924 (12) | 0.00211 (12) | 0.00540 (10) | 0.00198 (11) |
C1—N1 | 1.324 (3) | C16—C17 | 1.379 (3) |
C1—C2 | 1.401 (3) | C16—C21 | 1.387 (3) |
C1—H1 | 0.9300 | C17—C18 | 1.386 (3) |
C2—C3 | 1.375 (3) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—C19 | 1.382 (3) |
C3—C4 | 1.401 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.374 (3) |
C4—C5 | 1.397 (3) | C19—O3 | 1.387 (3) |
C4—C12 | 1.456 (3) | C20—C21 | 1.382 (3) |
C5—N1 | 1.354 (3) | C20—H20 | 0.9300 |
C5—C6 | 1.437 (3) | C21—H21 | 0.9300 |
C6—N2 | 1.357 (3) | C22—C28 | 1.386 (3) |
C6—C10 | 1.397 (3) | C22—C23 | 1.384 (3) |
C7—N2 | 1.323 (3) | C22—H22 | 0.9300 |
C7—C8 | 1.392 (3) | C23—C25 | 1.389 (3) |
C7—H7 | 0.9300 | C23—C24 | 1.504 (3) |
C8—C9 | 1.371 (3) | C24—O4 | 1.225 (3) |
C8—H8 | 0.9300 | C24—O5 | 1.281 (3) |
C9—C10 | 1.399 (3) | C25—C26 | 1.379 (3) |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C10—C11 | 1.460 (3) | C26—C27 | 1.380 (3) |
C11—N4 | 1.356 (3) | C26—H26 | 0.9300 |
C11—C12 | 1.394 (4) | C27—C28 | 1.379 (3) |
C12—N3 | 1.353 (3) | C27—O3 | 1.386 (2) |
C13—N3 | 1.321 (4) | C28—H28 | 0.9300 |
C13—C14 | 1.380 (5) | Cu1—N1 | 2.0052 (18) |
C13—H13 | 0.9300 | Cu1—N2 | 2.0038 (18) |
C14—N4 | 1.322 (4) | Cu1—O1 | 1.9279 (17) |
C14—H14 | 0.9300 | O1W—HW11 | 0.81 (3) |
C15—O2 | 1.222 (3) | O1W—HW12 | 0.89 (4) |
C15—O1 | 1.271 (3) | Cu1—O5i | 1.9165 (17) |
C15—C16 | 1.501 (3) | ||
N1—C1—C2 | 122.1 (2) | C19—C18—C17 | 118.8 (2) |
N1—C1—H1 | 118.9 | C19—C18—H18 | 120.6 |
C2—C1—H1 | 118.9 | C17—C18—H18 | 120.6 |
C3—C2—C1 | 119.3 (2) | C20—C19—C18 | 120.8 (2) |
C3—C2—H2 | 120.3 | C20—C19—O3 | 115.8 (2) |
C1—C2—H2 | 120.3 | C18—C19—O3 | 123.1 (2) |
C2—C3—C4 | 119.3 (2) | C19—C20—C21 | 119.9 (2) |
C2—C3—H3 | 120.3 | C19—C20—H20 | 120.1 |
C4—C3—H3 | 120.3 | C21—C20—H20 | 120.1 |
C5—C4—C3 | 117.7 (2) | C20—C21—C16 | 120.2 (2) |
C5—C4—C12 | 117.9 (2) | C20—C21—H21 | 119.9 |
C3—C4—C12 | 124.4 (2) | C16—C21—H21 | 119.9 |
N1—C5—C4 | 122.7 (2) | C28—C22—C23 | 121.1 (2) |
N1—C5—C6 | 116.26 (18) | C28—C22—H22 | 119.5 |
C4—C5—C6 | 121.07 (19) | C23—C22—H22 | 119.5 |
N2—C6—C10 | 122.3 (2) | C22—C23—C25 | 118.9 (2) |
N2—C6—C5 | 116.04 (18) | C22—C23—C24 | 120.2 (2) |
C10—C6—C5 | 121.66 (19) | C25—C23—C24 | 120.9 (2) |
N2—C7—C8 | 121.5 (2) | O4—C24—O5 | 124.6 (2) |
N2—C7—H7 | 119.2 | O4—C24—C23 | 120.4 (2) |
C8—C7—H7 | 119.2 | O5—C24—C23 | 115.0 (2) |
C9—C8—C7 | 120.2 (2) | C26—C25—C23 | 120.5 (2) |
C9—C8—H8 | 119.9 | C26—C25—H25 | 119.7 |
C7—C8—H8 | 119.9 | C23—C25—H25 | 119.7 |
C8—C9—C10 | 119.0 (2) | C25—C26—C27 | 119.7 (2) |
C8—C9—H9 | 120.5 | C25—C26—H26 | 120.1 |
C10—C9—H9 | 120.5 | C27—C26—H26 | 120.1 |
C6—C10—C9 | 117.7 (2) | C28—C27—C26 | 120.8 (2) |
C6—C10—C11 | 117.6 (2) | C28—C27—O3 | 124.1 (2) |
C9—C10—C11 | 124.6 (2) | C26—C27—O3 | 114.9 (2) |
N4—C11—C12 | 121.4 (2) | C27—C28—C22 | 119.0 (2) |
N4—C11—C10 | 117.8 (2) | C27—C28—H28 | 120.5 |
C12—C11—C10 | 120.71 (19) | C22—C28—H28 | 120.5 |
N3—C12—C11 | 121.6 (2) | C1—N1—C5 | 118.86 (18) |
N3—C12—C4 | 117.4 (2) | C1—N1—Cu1 | 128.39 (15) |
C11—C12—C4 | 121.01 (19) | C5—N1—Cu1 | 112.75 (14) |
N3—C13—C14 | 123.1 (2) | C7—N2—C6 | 119.19 (18) |
N3—C13—H13 | 118.5 | C7—N2—Cu1 | 127.99 (15) |
C14—C13—H13 | 118.5 | C6—N2—Cu1 | 112.81 (14) |
N4—C14—C13 | 122.5 (2) | C13—N3—C12 | 115.6 (3) |
N4—C14—H14 | 118.7 | C14—N4—C11 | 115.8 (3) |
C13—C14—H14 | 118.7 | C15—O1—Cu1 | 110.98 (16) |
O2—C15—O1 | 124.0 (2) | HW11—O1W—HW12 | 111 (3) |
O2—C15—C16 | 119.8 (3) | C27—O3—C19 | 121.76 (18) |
O1—C15—C16 | 116.2 (2) | C24—O5—Cu1ii | 112.20 (15) |
C17—C16—C21 | 119.2 (2) | O5i—Cu1—O1 | 90.49 (8) |
C17—C16—C15 | 120.5 (2) | O5i—Cu1—N2 | 175.81 (7) |
C21—C16—C15 | 120.3 (2) | O1—Cu1—N2 | 93.69 (8) |
C16—C17—C18 | 121.0 (2) | O5i—Cu1—N1 | 93.75 (8) |
C16—C17—H17 | 119.5 | O1—Cu1—N1 | 175.61 (7) |
C18—C17—H17 | 119.5 | N2—Cu1—N1 | 82.06 (7) |
Symmetry codes: (i) −x−1/2, y−1/2, −z+1/2; (ii) −x−1/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW11···O2 | 0.81 (3) | 2.22 (5) | 2.808 (3) | 129 (4) |
Experimental details
Crystal data | |
Chemical formula | [Cu(C14H8O5)(C14H8N4)]·H2O |
Mr | 570.00 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 5.8092 (12), 14.635 (3), 27.600 (6) |
β (°) | 91.87 (3) |
V (Å3) | 2345.2 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.22 × 0.19 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.801, 0.837 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21478, 5350, 4136 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.093, 0.93 |
No. of reflections | 5350 |
No. of parameters | 358 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.28 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Cu1—N1 | 2.0052 (18) | Cu1—O1 | 1.9279 (17) |
Cu1—N2 | 2.0038 (18) | Cu1—O5i | 1.9165 (17) |
Symmetry code: (i) −x−1/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW11···O2 | 0.81 (3) | 2.22 (5) | 2.808 (3) | 129 (4) |
Studies on metal dicarboxylato complexes with heteroaromatic N-donor chelating ligands are of current interest (Chen & Liu, 2002). Pyrazino[2,3-f][1,10]phenanthroline (Pyphen) as a new phen derivative possesses an extended aromatic system. We selected 4,4'-oxybis(benzoic acid) (H2L) as a linker and Pyphen as a secondary chelating ligand, and in combination with Cu2+ ions, generaed the new coordination polymer, [Cu(L)(Pyphen)].H2O, (I), which is reported here.
In compound (I) the CuII atom is four-coordinated by two Pyphen N atoms and two carboxylate O atoms, and exhibits a distorted square-planar coordination sphere (Table 1, Fig. 1). The L ligands link the CuII atoms to generate a distinctive helical chain structure (Fig. 2). The Pyphen ligands are attached on both sides of the chains. The neighbouring chains are linked through π-π interactions between Pyphen ligands with a π-π stacking distance of ca 3.44 Å, resulting in a two-dimensional supramolecular structure (Fig. 3). Finally, O—H···O hydrogen bonds involving the water molecule and carboxylate O atom acceptors (Table 2) complete the structure of (I).