Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704723X/ci2473sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704723X/ci2473Isup2.hkl |
CCDC reference: 667098
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.101
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
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) 2.24 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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), H2dpdc (0.5 mmol), mi (0.5 mmol), and H2O (500 mmol) was adjusted to pH=5.8 by addition of aqueous NaOH solution, and heated at 458 K for 2 d. After the mixture was slowly cooled to room temperature, blue crystals of (I) were obtained (yield 27%).
C– and N-bound H atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier). The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85 Å The Uij components of atom O1 were approximated to isotropic behaviour.
Helical or chain structures have received much attention in coordination chemistry (Chen & Liu, 2002). An appropriate bidentate carboxylate could be useful in the formation of helical chains in the presence of secondary ligands (Lehn, 1990). 2,2'-Diphenyldicarboxylic acid (H2dpdc) is a benzoic acid-based ligand, where the two phenyl rings can freely twist to meet the requirements of the coordination geometries of metal ions in the assembly process. We selected H2dpdc as a bridging ligand and 2-methyl-1H-imidazole (mi) as a secondary ligand, generating a new zigzag chain coordination polymer, [Cu(dpdc)(mi)2].2H2O, (I), which is reported here.
Selected bond lengths and angles are listed in Table 1. In the title compound, each CuII atom is four-coordinated by two N atoms from two mi ligands, and two O atoms from two dpdc ligands in a square-planar coordination environment (Fig. 1). The Cu—O distances vary from 1.9488 (17) to 2.0005 (18) Å (Table 1), and the Cu1—N3 and Cu1—N1 distances are 1.960 (2) and 1.994 (2) Å, respectively. Each dpdc ligand bridges two neighboring CuII atoms in a bis-monodentate mode, forming a zigzag chain along the b axis (Fig. 2). The chain is decorated with mi ligands alternately at two sides. Furthermore, the O—H···O and N—H···O hydrogen bonds (Table 2) link the chains together, resulting in a supramolecular structure.
For related literature, see: Chen & Liu (2002); De (2007); Lehn (1990).
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(C14H8O4)(C4H6N2)2]·2H2O | F(000) = 1044 |
Mr = 503.99 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 17307 reflections |
a = 8.7554 (18) Å | θ = 3.0–27.5° |
b = 17.940 (4) Å | µ = 0.94 mm−1 |
c = 16.116 (3) Å | T = 293 K |
β = 104.65 (3)° | Block, blue |
V = 2449.0 (9) Å3 | 0.33 × 0.25 × 0.19 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5578 independent reflections |
Radiation source: rotating anode | 4004 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −23→23 |
Tmin = 0.731, Tmax = 0.836 | l = −20→20 |
23229 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0409P)2 + 1.0153P] where P = (Fo2 + 2Fc2)/3 |
5578 reflections | (Δ/σ)max = 0.001 |
316 parameters | Δρmax = 0.47 e Å−3 |
12 restraints | Δρmin = −0.32 e Å−3 |
[Cu(C14H8O4)(C4H6N2)2]·2H2O | V = 2449.0 (9) Å3 |
Mr = 503.99 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7554 (18) Å | µ = 0.94 mm−1 |
b = 17.940 (4) Å | T = 293 K |
c = 16.116 (3) Å | 0.33 × 0.25 × 0.19 mm |
β = 104.65 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5578 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4004 reflections with I > 2σ(I) |
Tmin = 0.731, Tmax = 0.836 | Rint = 0.056 |
23229 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 12 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.47 e Å−3 |
5578 reflections | Δρmin = −0.32 e Å−3 |
316 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 | −0.0628 (3) | 0.14907 (16) | 0.89714 (17) | 0.0417 (6) | |
C2 | 0.0462 (4) | 0.09492 (19) | 0.9508 (2) | 0.0650 (9) | |
H2A | −0.0049 | 0.0716 | 0.9902 | 0.097* | |
H2B | 0.1394 | 0.1203 | 0.9822 | 0.097* | |
H2C | 0.0748 | 0.0576 | 0.9147 | 0.097* | |
C3 | −0.2843 (4) | 0.2071 (2) | 0.8369 (2) | 0.0628 (9) | |
H3 | −0.3902 | 0.2207 | 0.8210 | 0.075* | |
C4 | −0.1646 (3) | 0.23935 (19) | 0.81210 (19) | 0.0527 (8) | |
H4 | −0.1740 | 0.2799 | 0.7752 | 0.063* | |
C5 | 0.1416 (4) | 0.29497 (18) | 1.00860 (19) | 0.0521 (7) | |
H5 | 0.0352 | 0.3051 | 0.9852 | 0.063* | |
C6 | 0.2215 (4) | 0.3096 (2) | 1.0897 (2) | 0.0588 (8) | |
H6 | 0.1819 | 0.3315 | 1.1322 | 0.071* | |
C7 | 0.3821 (3) | 0.25763 (16) | 1.02174 (17) | 0.0444 (6) | |
C8 | 0.5277 (4) | 0.2251 (2) | 1.0070 (2) | 0.0699 (10) | |
H8A | 0.5976 | 0.2116 | 1.0610 | 0.105* | |
H8B | 0.5784 | 0.2609 | 0.9788 | 0.105* | |
H8C | 0.5017 | 0.1815 | 0.9717 | 0.105* | |
C9 | 0.3097 (3) | 0.34777 (15) | 0.78098 (17) | 0.0381 (6) | |
C10 | 0.4314 (3) | 0.40035 (15) | 0.76376 (17) | 0.0397 (6) | |
C11 | 0.5341 (4) | 0.37354 (18) | 0.7172 (2) | 0.0581 (8) | |
H11 | 0.5226 | 0.3250 | 0.6964 | 0.070* | |
C12 | 0.6531 (4) | 0.4179 (2) | 0.7015 (2) | 0.0695 (11) | |
H12 | 0.7201 | 0.3994 | 0.6699 | 0.083* | |
C13 | 0.6715 (4) | 0.4893 (2) | 0.7328 (2) | 0.0679 (10) | |
H13 | 0.7528 | 0.5189 | 0.7236 | 0.081* | |
C14 | 0.5691 (4) | 0.51740 (18) | 0.7781 (2) | 0.0558 (8) | |
H14 | 0.5817 | 0.5662 | 0.7981 | 0.067* | |
C15 | 0.4473 (3) | 0.47388 (15) | 0.79433 (17) | 0.0398 (6) | |
C16 | 0.3490 (3) | 0.50494 (15) | 0.84949 (17) | 0.0409 (6) | |
C17 | 0.3339 (4) | 0.46496 (17) | 0.92179 (19) | 0.0540 (8) | |
H17 | 0.3793 | 0.4179 | 0.9322 | 0.065* | |
C18 | 0.2531 (5) | 0.4938 (2) | 0.9781 (2) | 0.0700 (10) | |
H18 | 0.2425 | 0.4659 | 1.0249 | 0.084* | |
C19 | 0.1889 (5) | 0.5637 (2) | 0.9645 (2) | 0.0805 (12) | |
H19 | 0.1351 | 0.5834 | 1.0024 | 0.097* | |
C20 | 0.2040 (5) | 0.60497 (19) | 0.8946 (2) | 0.0682 (10) | |
H20 | 0.1615 | 0.6527 | 0.8863 | 0.082* | |
C21 | 0.2815 (3) | 0.57618 (15) | 0.83676 (17) | 0.0429 (6) | |
C22 | 0.2822 (3) | 0.62358 (15) | 0.75948 (18) | 0.0414 (6) | |
N1 | 0.2424 (3) | 0.26251 (13) | 0.96545 (14) | 0.0411 (5) | |
N2 | 0.3718 (3) | 0.28605 (15) | 1.09724 (15) | 0.0528 (6) | |
H2 | 0.4479 | 0.2889 | 1.1429 | 0.063* | |
N3 | −0.0259 (2) | 0.20308 (13) | 0.84973 (13) | 0.0394 (5) | |
N4 | −0.2186 (3) | 0.15028 (15) | 0.89015 (16) | 0.0530 (6) | |
H4A | −0.2689 | 0.1201 | 0.9152 | 0.064* | |
O1 | 0.1663 (2) | 0.36111 (11) | 0.75780 (13) | 0.0527 (5) | |
O2 | 0.3644 (2) | 0.28816 (10) | 0.82080 (11) | 0.0399 (4) | |
O1W | −0.3240 (3) | 0.03831 (16) | 0.9770 (2) | 0.0705 (7) | |
O3 | 0.2146 (3) | 0.60283 (11) | 0.68615 (13) | 0.0564 (5) | |
O2W | 0.0770 (3) | 0.46838 (15) | 0.63200 (15) | 0.0693 (7) | |
O4 | 0.3503 (2) | 0.68677 (10) | 0.77385 (11) | 0.0412 (4) | |
Cu1 | 0.18444 (3) | 0.234302 (17) | 0.841723 (19) | 0.03370 (10) | |
HW11 | −0.343 (4) | 0.040 (2) | 1.0252 (14) | 0.092 (15)* | |
HW12 | −0.387 (3) | 0.0107 (17) | 0.9426 (16) | 0.067 (12)* | |
HW21 | 0.098 (4) | 0.4360 (15) | 0.6711 (19) | 0.085 (13)* | |
HW22 | 0.117 (5) | 0.5101 (13) | 0.653 (2) | 0.104 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0451 (15) | 0.0391 (15) | 0.0404 (15) | −0.0007 (12) | 0.0100 (12) | −0.0022 (12) |
C2 | 0.064 (2) | 0.056 (2) | 0.074 (2) | 0.0047 (17) | 0.0160 (18) | 0.0243 (18) |
C3 | 0.0450 (17) | 0.091 (3) | 0.055 (2) | 0.0161 (17) | 0.0183 (15) | 0.0137 (18) |
C4 | 0.0500 (16) | 0.065 (2) | 0.0435 (16) | 0.0158 (15) | 0.0132 (13) | 0.0115 (15) |
C5 | 0.0534 (17) | 0.0579 (19) | 0.0472 (18) | 0.0024 (15) | 0.0166 (14) | −0.0099 (15) |
C6 | 0.065 (2) | 0.069 (2) | 0.0455 (18) | −0.0003 (17) | 0.0192 (16) | −0.0166 (16) |
C7 | 0.0541 (16) | 0.0437 (16) | 0.0335 (14) | 0.0004 (13) | 0.0075 (12) | −0.0014 (12) |
C8 | 0.0571 (19) | 0.095 (3) | 0.052 (2) | 0.0228 (19) | 0.0043 (16) | −0.0044 (19) |
C9 | 0.0462 (15) | 0.0306 (14) | 0.0399 (15) | 0.0026 (12) | 0.0150 (12) | −0.0013 (11) |
C10 | 0.0447 (14) | 0.0344 (14) | 0.0419 (15) | 0.0066 (12) | 0.0144 (12) | 0.0114 (12) |
C11 | 0.071 (2) | 0.0449 (18) | 0.067 (2) | 0.0132 (16) | 0.0320 (18) | 0.0109 (15) |
C12 | 0.071 (2) | 0.071 (3) | 0.083 (3) | 0.0221 (19) | 0.049 (2) | 0.032 (2) |
C13 | 0.0544 (19) | 0.062 (2) | 0.095 (3) | 0.0034 (17) | 0.0333 (19) | 0.034 (2) |
C14 | 0.0557 (18) | 0.0437 (17) | 0.068 (2) | −0.0022 (15) | 0.0153 (16) | 0.0164 (15) |
C15 | 0.0432 (14) | 0.0341 (14) | 0.0411 (15) | 0.0018 (12) | 0.0086 (12) | 0.0127 (12) |
C16 | 0.0511 (15) | 0.0342 (15) | 0.0371 (14) | −0.0044 (12) | 0.0106 (12) | 0.0030 (11) |
C17 | 0.076 (2) | 0.0389 (17) | 0.0474 (17) | −0.0025 (15) | 0.0164 (16) | 0.0080 (13) |
C18 | 0.109 (3) | 0.057 (2) | 0.053 (2) | −0.001 (2) | 0.039 (2) | 0.0134 (16) |
C19 | 0.132 (4) | 0.057 (2) | 0.074 (3) | 0.013 (2) | 0.065 (3) | 0.0047 (19) |
C20 | 0.106 (3) | 0.0456 (19) | 0.066 (2) | 0.0128 (19) | 0.045 (2) | 0.0068 (16) |
C21 | 0.0554 (16) | 0.0351 (15) | 0.0404 (15) | −0.0004 (13) | 0.0163 (13) | 0.0064 (12) |
C22 | 0.0495 (15) | 0.0342 (15) | 0.0425 (16) | 0.0069 (12) | 0.0153 (13) | 0.0036 (12) |
N1 | 0.0453 (12) | 0.0425 (13) | 0.0351 (12) | −0.0010 (11) | 0.0092 (10) | −0.0045 (10) |
N2 | 0.0574 (15) | 0.0622 (17) | 0.0339 (13) | −0.0017 (13) | 0.0027 (11) | −0.0090 (11) |
N3 | 0.0407 (12) | 0.0406 (13) | 0.0352 (12) | 0.0008 (10) | 0.0066 (10) | 0.0047 (10) |
N4 | 0.0478 (14) | 0.0635 (17) | 0.0538 (15) | −0.0040 (13) | 0.0239 (12) | 0.0033 (13) |
O1 | 0.0491 (8) | 0.0475 (9) | 0.0609 (9) | 0.0017 (7) | 0.0128 (7) | 0.0060 (7) |
O2 | 0.0460 (10) | 0.0300 (9) | 0.0425 (11) | −0.0002 (8) | 0.0090 (8) | 0.0062 (8) |
O1W | 0.0589 (15) | 0.0783 (19) | 0.0736 (18) | −0.0173 (13) | 0.0155 (14) | 0.0119 (15) |
O3 | 0.0795 (15) | 0.0430 (12) | 0.0420 (12) | −0.0114 (11) | 0.0065 (11) | 0.0007 (9) |
O2W | 0.0917 (18) | 0.0457 (15) | 0.0552 (14) | −0.0042 (13) | −0.0099 (13) | 0.0049 (12) |
O4 | 0.0513 (11) | 0.0327 (10) | 0.0383 (10) | −0.0024 (8) | 0.0089 (8) | 0.0039 (8) |
Cu1 | 0.03913 (17) | 0.02943 (16) | 0.03139 (16) | 0.00027 (14) | 0.00683 (12) | 0.00007 (14) |
C1—N3 | 1.324 (3) | C12—H12 | 0.93 |
C1—N4 | 1.340 (3) | C13—C14 | 1.386 (5) |
C1—C2 | 1.478 (4) | C13—H13 | 0.93 |
C2—H2A | 0.96 | C14—C15 | 1.399 (4) |
C2—H2B | 0.96 | C14—H14 | 0.93 |
C2—H2C | 0.96 | C15—C16 | 1.493 (4) |
C3—C4 | 1.344 (4) | C16—C21 | 1.401 (4) |
C3—N4 | 1.363 (4) | C16—C17 | 1.403 (4) |
C3—H3 | 0.93 | C17—C18 | 1.384 (4) |
C4—N3 | 1.376 (3) | C17—H17 | 0.93 |
C4—H4 | 0.93 | C18—C19 | 1.369 (5) |
C5—C6 | 1.343 (4) | C18—H18 | 0.93 |
C5—N1 | 1.383 (4) | C19—C20 | 1.383 (4) |
C5—H5 | 0.93 | C19—H19 | 0.93 |
C6—N2 | 1.357 (4) | C20—C21 | 1.384 (4) |
C6—H6 | 0.93 | C20—H20 | 0.93 |
C7—N1 | 1.328 (4) | C21—C22 | 1.509 (4) |
C7—N2 | 1.343 (3) | C22—O3 | 1.238 (3) |
C7—C8 | 1.475 (4) | C22—O4 | 1.274 (3) |
C8—H8A | 0.96 | Cu1—N1 | 1.994 (2) |
C8—H8B | 0.96 | N2—H2 | 0.86 |
C8—H8C | 0.96 | Cu1—N3 | 1.960 (2) |
C9—O1 | 1.240 (3) | N4—H4A | 0.86 |
C9—O2 | 1.276 (3) | Cu1—O2 | 1.9488 (17) |
C9—C10 | 1.500 (4) | O1W—HW11 | 0.837 (17) |
C10—C11 | 1.395 (4) | O1W—HW12 | 0.840 (17) |
C10—C15 | 1.403 (4) | O2W—HW21 | 0.842 (17) |
C11—C12 | 1.384 (5) | O2W—HW22 | 0.859 (18) |
C11—H11 | 0.93 | O4—Cu1i | 2.0005 (18) |
C12—C13 | 1.371 (5) | Cu1—O4ii | 2.0005 (18) |
N3—C1—N4 | 109.4 (2) | C15—C14—H14 | 119.3 |
N3—C1—C2 | 127.1 (3) | C14—C15—C10 | 118.2 (3) |
N4—C1—C2 | 123.6 (3) | C14—C15—C16 | 119.0 (3) |
C1—C2—H2A | 109.5 | C10—C15—C16 | 122.6 (2) |
C1—C2—H2B | 109.5 | C21—C16—C17 | 117.6 (2) |
H2A—C2—H2B | 109.5 | C21—C16—C15 | 122.6 (2) |
C1—C2—H2C | 109.5 | C17—C16—C15 | 119.6 (3) |
H2A—C2—H2C | 109.5 | C18—C17—C16 | 121.6 (3) |
H2B—C2—H2C | 109.5 | C18—C17—H17 | 119.2 |
C4—C3—N4 | 105.8 (3) | C16—C17—H17 | 119.2 |
C4—C3—H3 | 127.1 | C19—C18—C17 | 119.7 (3) |
N4—C3—H3 | 127.1 | C19—C18—H18 | 120.1 |
C3—C4—N3 | 109.5 (3) | C17—C18—H18 | 120.1 |
C3—C4—H4 | 125.3 | C18—C19—C20 | 120.0 (3) |
N3—C4—H4 | 125.3 | C18—C19—H19 | 120.0 |
C6—C5—N1 | 109.3 (3) | C20—C19—H19 | 120.0 |
C6—C5—H5 | 125.4 | C19—C20—C21 | 120.9 (3) |
N1—C5—H5 | 125.4 | C19—C20—H20 | 119.5 |
C5—C6—N2 | 106.3 (3) | C21—C20—H20 | 119.5 |
C5—C6—H6 | 126.8 | C20—C21—C16 | 120.2 (3) |
N2—C6—H6 | 126.8 | C20—C21—C22 | 116.8 (3) |
N1—C7—N2 | 109.4 (3) | C16—C21—C22 | 123.0 (2) |
N1—C7—C8 | 126.9 (3) | O3—C22—O4 | 122.0 (2) |
N2—C7—C8 | 123.7 (3) | O3—C22—C21 | 121.2 (3) |
C7—C8—H8A | 109.5 | O4—C22—C21 | 116.8 (2) |
C7—C8—H8B | 109.5 | C7—N1—C5 | 106.2 (2) |
H8A—C8—H8B | 109.5 | C7—N1—Cu1 | 128.57 (19) |
C7—C8—H8C | 109.5 | C5—N1—Cu1 | 125.17 (19) |
H8A—C8—H8C | 109.5 | C7—N2—C6 | 108.8 (3) |
H8B—C8—H8C | 109.5 | C7—N2—H2 | 125.6 |
O1—C9—O2 | 122.4 (2) | C6—N2—H2 | 125.6 |
O1—C9—C10 | 122.4 (2) | C1—N3—C4 | 106.5 (2) |
O2—C9—C10 | 115.3 (2) | C1—N3—Cu1 | 128.17 (19) |
C11—C10—C15 | 119.5 (3) | C4—N3—Cu1 | 125.1 (2) |
C11—C10—C9 | 117.9 (3) | C1—N4—C3 | 108.9 (2) |
C15—C10—C9 | 122.6 (2) | C1—N4—H4A | 125.6 |
C12—C11—C10 | 121.2 (3) | C3—N4—H4A | 125.6 |
C12—C11—H11 | 119.4 | C9—O2—Cu1 | 106.61 (16) |
C10—C11—H11 | 119.4 | HW11—O1W—HW12 | 112 (3) |
C13—C12—C11 | 119.6 (3) | HW21—O2W—HW22 | 109 (3) |
C13—C12—H12 | 120.2 | C22—O4—Cu1i | 104.84 (16) |
C11—C12—H12 | 120.2 | O2—Cu1—N3 | 165.28 (8) |
C12—C13—C14 | 120.1 (3) | O2—Cu1—N1 | 91.99 (9) |
C12—C13—H13 | 119.9 | N3—Cu1—N1 | 90.72 (9) |
C14—C13—H13 | 119.9 | O2—Cu1—O4ii | 89.39 (8) |
C13—C14—C15 | 121.4 (3) | N3—Cu1—O4ii | 90.88 (9) |
C13—C14—H14 | 119.3 | N1—Cu1—O4ii | 168.31 (8) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW12···O2Wiii | 0.84 (2) | 1.94 (2) | 2.757 (4) | 163 (3) |
O1W—HW11···O2Wiv | 0.84 (2) | 2.02 (2) | 2.846 (4) | 169 (3) |
O2W—HW21···O1 | 0.84 (2) | 1.92 (2) | 2.761 (3) | 174 (4) |
O2W—HW22···O3 | 0.86 (2) | 1.88 (2) | 2.738 (3) | 173 (4) |
N2—H2···O4v | 0.86 | 1.98 | 2.814 (3) | 164 |
N4—H4A···O1W | 0.86 | 1.90 | 2.738 (4) | 163 |
Symmetry codes: (iii) −x−1/2, y−1/2, −z+3/2; (iv) x−1/2, −y+1/2, z+1/2; (v) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C14H8O4)(C4H6N2)2]·2H2O |
Mr | 503.99 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.7554 (18), 17.940 (4), 16.116 (3) |
β (°) | 104.65 (3) |
V (Å3) | 2449.0 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.94 |
Crystal size (mm) | 0.33 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.731, 0.836 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23229, 5578, 4004 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.101, 1.04 |
No. of reflections | 5578 |
No. of parameters | 316 |
No. of restraints | 12 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.32 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Cu1—N1 | 1.994 (2) | Cu1—O2 | 1.9488 (17) |
Cu1—N3 | 1.960 (2) | Cu1—O4i | 2.0005 (18) |
O2—Cu1—N3 | 165.28 (8) | O2—Cu1—O4i | 89.39 (8) |
O2—Cu1—N1 | 91.99 (9) | N3—Cu1—O4i | 90.88 (9) |
N3—Cu1—N1 | 90.72 (9) | N1—Cu1—O4i | 168.31 (8) |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW12···O2Wii | 0.840 (17) | 1.94 (2) | 2.757 (4) | 163 (3) |
O1W—HW11···O2Wiii | 0.837 (17) | 2.02 (2) | 2.846 (4) | 169 (3) |
O2W—HW21···O1 | 0.842 (17) | 1.922 (18) | 2.761 (3) | 174 (4) |
O2W—HW22···O3 | 0.859 (18) | 1.884 (18) | 2.738 (3) | 173 (4) |
N2—H2···O4iv | 0.86 | 1.98 | 2.814 (3) | 164 |
N4—H4A···O1W | 0.86 | 1.90 | 2.738 (4) | 163 |
Symmetry codes: (ii) −x−1/2, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+2. |
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Helical or chain structures have received much attention in coordination chemistry (Chen & Liu, 2002). An appropriate bidentate carboxylate could be useful in the formation of helical chains in the presence of secondary ligands (Lehn, 1990). 2,2'-Diphenyldicarboxylic acid (H2dpdc) is a benzoic acid-based ligand, where the two phenyl rings can freely twist to meet the requirements of the coordination geometries of metal ions in the assembly process. We selected H2dpdc as a bridging ligand and 2-methyl-1H-imidazole (mi) as a secondary ligand, generating a new zigzag chain coordination polymer, [Cu(dpdc)(mi)2].2H2O, (I), which is reported here.
Selected bond lengths and angles are listed in Table 1. In the title compound, each CuII atom is four-coordinated by two N atoms from two mi ligands, and two O atoms from two dpdc ligands in a square-planar coordination environment (Fig. 1). The Cu—O distances vary from 1.9488 (17) to 2.0005 (18) Å (Table 1), and the Cu1—N3 and Cu1—N1 distances are 1.960 (2) and 1.994 (2) Å, respectively. Each dpdc ligand bridges two neighboring CuII atoms in a bis-monodentate mode, forming a zigzag chain along the b axis (Fig. 2). The chain is decorated with mi ligands alternately at two sides. Furthermore, the O—H···O and N—H···O hydrogen bonds (Table 2) link the chains together, resulting in a supramolecular structure.