Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705996X/rz2175sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705996X/rz2175Isup2.hkl |
CCDC reference: 672748
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.046
- wR factor = 0.123
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C12 .. 7.11 su
Alert level C PLAT128_ALERT_4_C Non-standard setting of Space-group P2/c .... P2/n PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc.
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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Yang et al. (2007); Yang, Ma et al. (2006); Yang, Yue et al. (2006).
A mixture of CuCl2.2H2O (86.0 mg, 0.5 mmol) and NaOH (40 mg, 1 mmol) in 20 ml water was stirred for 10 min at room temperature, then the Cu(OH)2 precipitate was filtered. HBA (122.0 mg, 1 mmol) was added to the Cu(OH)2 suspension in C2H5OH/H2O (1:4 v/v) with constant stirring for 1 h until a blue precipitate was obtained. The solid was filtered off and washed with water, then BIE (103.1 mg, 0.5 mmol) was added with stirring for 1 h to give a blue solution. Blue crystals of the title compound were obtained on slow evaporation of the solvent at room temperature.
All H atoms bound to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93–0.97 Å and Uiso = 1.2Ueq(C). The independent water H atom was located in a difference Fourier map and refined with Uiso(H) = 1.5Ueq(O) and with the O—H distance constrained to 0.85 Å.
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(C7H5O2)2(C10H14N4O)]·H2O | F(000) = 550 |
Mr = 530.04 | Dx = 1.493 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yac | Cell parameters from 7716 reflections |
a = 11.4960 (15) Å | θ = 3.0–27.5° |
b = 7.7400 (16) Å | µ = 0.97 mm−1 |
c = 13.609 (3) Å | T = 293 K |
β = 103.140 (3)° | Block, blue |
V = 1179.2 (4) Å3 | 0.11 × 0.11 × 0.10 mm |
Z = 2 |
Rigaku RAXIS-RAPID diffractometer | 2697 independent reflections |
Radiation source: rotor target | 1980 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −14→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −10→10 |
Tmin = 0.901, Tmax = 0.907 | l = −17→17 |
10769 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0457P)2 + 0.8067P] where P = (Fo2 + 2Fc2)/3 |
2697 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.44 e Å−3 |
1 restraint | Δρmin = −0.51 e Å−3 |
[Cu(C7H5O2)2(C10H14N4O)]·H2O | V = 1179.2 (4) Å3 |
Mr = 530.04 | Z = 2 |
Monoclinic, P2/n | Mo Kα radiation |
a = 11.4960 (15) Å | µ = 0.97 mm−1 |
b = 7.7400 (16) Å | T = 293 K |
c = 13.609 (3) Å | 0.11 × 0.11 × 0.10 mm |
β = 103.140 (3)° |
Rigaku RAXIS-RAPID diffractometer | 2697 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1980 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.907 | Rint = 0.054 |
10769 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 1 restraint |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.44 e Å−3 |
2697 reflections | Δρmin = −0.51 e Å−3 |
183 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 | Occ. (<1) | |
Cu1 | 0.0000 | 0.0000 | 0.5000 | 0.03667 (17) | |
C1 | 0.0488 (3) | −0.3199 (5) | 0.6225 (3) | 0.0655 (10) | |
H1 | 0.1290 | −0.2915 | 0.6450 | 0.079* | |
C2 | −0.1193 (3) | −0.4557 (5) | 0.6050 (3) | 0.0616 (10) | |
H2 | −0.1777 | −0.5356 | 0.6112 | 0.074* | |
C3 | −0.1333 (3) | −0.3151 (5) | 0.5459 (3) | 0.0590 (9) | |
H3 | −0.2051 | −0.2808 | 0.5038 | 0.071* | |
C4 | 0.2271 (2) | −0.0881 (4) | 0.5132 (2) | 0.0400 (6) | |
C5 | 0.3558 (2) | −0.1290 (4) | 0.5583 (2) | 0.0403 (6) | |
C6 | 0.4217 (3) | −0.2260 (5) | 0.5036 (2) | 0.0508 (8) | |
H6 | 0.3858 | −0.2661 | 0.4394 | 0.061* | |
C7 | 0.5408 (3) | −0.2624 (6) | 0.5451 (3) | 0.0649 (10) | |
H7 | 0.5844 | −0.3279 | 0.5087 | 0.078* | |
C8 | 0.5948 (3) | −0.2028 (6) | 0.6391 (3) | 0.0669 (10) | |
H8 | 0.6750 | −0.2266 | 0.6660 | 0.080* | |
C9 | 0.5303 (3) | −0.1074 (5) | 0.6939 (3) | 0.0620 (10) | |
H9 | 0.5670 | −0.0660 | 0.7575 | 0.074* | |
C10 | 0.4102 (3) | −0.0734 (5) | 0.6537 (2) | 0.0501 (8) | |
H10 | 0.3662 | −0.0123 | 0.6917 | 0.060* | |
C11 | 0.0454 (8) | −0.6286 (12) | 0.6974 (8) | 0.050 (3) | 0.417 (12) |
H11A | −0.0168 | −0.6987 | 0.7149 | 0.060* | 0.417 (12) |
H11B | 0.0824 | −0.6922 | 0.6512 | 0.060* | 0.417 (12) |
C12 | 0.1351 (9) | −0.5730 (14) | 0.7888 (8) | 0.052 (3) | 0.417 (12) |
H12A | 0.1543 | −0.6674 | 0.8366 | 0.062* | 0.417 (12) |
H12B | 0.1049 | −0.4769 | 0.8214 | 0.062* | 0.417 (12) |
C11' | 0.0548 (7) | −0.5492 (11) | 0.7543 (7) | 0.060 (2) | 0.583 (12) |
H11C | 0.0745 | −0.4648 | 0.8082 | 0.072* | 0.583 (12) |
H11D | −0.0016 | −0.6309 | 0.7713 | 0.072* | 0.583 (12) |
C12' | 0.1665 (7) | −0.6430 (10) | 0.7439 (7) | 0.067 (2) | 0.583 (12) |
H12C | 0.1908 | −0.7266 | 0.7978 | 0.081* | 0.583 (12) |
H12D | 0.1538 | −0.7025 | 0.6796 | 0.081* | 0.583 (12) |
N1 | −0.0276 (2) | −0.2293 (3) | 0.55599 (18) | 0.0416 (6) | |
N2 | −0.0022 (3) | −0.4574 (4) | 0.6540 (3) | 0.0697 (10) | |
O1 | 0.18108 (18) | −0.1261 (3) | 0.42329 (15) | 0.0494 (5) | |
O2 | 0.16920 (18) | −0.0139 (3) | 0.57095 (15) | 0.0431 (5) | |
O3 | 0.2500 | −0.5163 (5) | 0.7500 | 0.0835 (14) | |
O1W | 0.2500 | −0.2648 (5) | 0.2500 | 0.0689 (10) | |
H1A | 0.263 (5) | −0.193 (4) | 0.207 (3) | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0352 (3) | 0.0402 (3) | 0.0364 (3) | 0.0039 (2) | 0.0117 (2) | 0.0030 (2) |
C1 | 0.0405 (17) | 0.071 (2) | 0.087 (3) | 0.0054 (17) | 0.0194 (17) | 0.038 (2) |
C2 | 0.054 (2) | 0.052 (2) | 0.079 (3) | −0.0057 (16) | 0.0169 (19) | 0.0142 (18) |
C3 | 0.0481 (18) | 0.057 (2) | 0.067 (2) | −0.0066 (16) | 0.0034 (16) | 0.0101 (18) |
C4 | 0.0366 (14) | 0.0382 (16) | 0.0452 (16) | −0.0012 (12) | 0.0097 (13) | 0.0063 (13) |
C5 | 0.0372 (14) | 0.0417 (16) | 0.0419 (15) | 0.0005 (13) | 0.0086 (12) | 0.0078 (13) |
C6 | 0.0413 (16) | 0.063 (2) | 0.0479 (17) | 0.0043 (15) | 0.0099 (13) | −0.0028 (16) |
C7 | 0.0435 (17) | 0.089 (3) | 0.065 (2) | 0.0157 (19) | 0.0173 (17) | 0.001 (2) |
C8 | 0.0405 (17) | 0.097 (3) | 0.060 (2) | 0.0116 (19) | 0.0038 (16) | 0.006 (2) |
C9 | 0.0521 (19) | 0.078 (3) | 0.0486 (18) | −0.0012 (19) | −0.0027 (16) | −0.0014 (18) |
C10 | 0.0482 (17) | 0.0537 (19) | 0.0476 (17) | 0.0018 (15) | 0.0094 (14) | −0.0010 (15) |
C11 | 0.058 (5) | 0.043 (5) | 0.045 (5) | −0.009 (4) | 0.004 (4) | 0.002 (4) |
C12 | 0.062 (6) | 0.046 (5) | 0.044 (5) | 0.003 (5) | 0.007 (5) | 0.011 (4) |
C11' | 0.063 (4) | 0.061 (5) | 0.054 (5) | −0.002 (4) | 0.007 (4) | 0.023 (4) |
C12' | 0.077 (5) | 0.047 (4) | 0.067 (5) | 0.013 (4) | −0.007 (4) | −0.005 (4) |
N1 | 0.0395 (12) | 0.0442 (14) | 0.0434 (13) | 0.0037 (11) | 0.0144 (11) | 0.0043 (11) |
N2 | 0.0497 (16) | 0.0665 (19) | 0.098 (2) | 0.0122 (15) | 0.0279 (17) | 0.0449 (18) |
O1 | 0.0429 (11) | 0.0594 (14) | 0.0441 (11) | 0.0040 (10) | 0.0060 (9) | −0.0014 (10) |
O2 | 0.0371 (10) | 0.0495 (12) | 0.0434 (11) | 0.0060 (9) | 0.0104 (9) | 0.0045 (9) |
O3 | 0.053 (2) | 0.058 (2) | 0.121 (4) | 0.000 | −0.019 (2) | 0.000 |
O1W | 0.095 (3) | 0.063 (2) | 0.053 (2) | 0.000 | 0.026 (2) | 0.000 |
Cu1—O2 | 1.968 (2) | C8—H8 | 0.9300 |
Cu1—O2i | 1.968 (2) | C9—C10 | 1.389 (4) |
Cu1—N1 | 1.985 (2) | C9—H9 | 0.9300 |
Cu1—N1i | 1.985 (2) | C10—H10 | 0.9300 |
C1—N1 | 1.311 (4) | C11—C12 | 1.487 (16) |
C1—N2 | 1.333 (4) | C11—N2 | 1.502 (9) |
C1—H1 | 0.9300 | C11—H11A | 0.9700 |
C2—C3 | 1.341 (5) | C11—H11B | 0.9700 |
C2—N2 | 1.360 (5) | C12—O3 | 1.591 (10) |
C2—H2 | 0.9300 | C12—H12A | 0.9700 |
C3—N1 | 1.364 (4) | C12—H12B | 0.9700 |
C3—H3 | 0.9300 | C11'—C12' | 1.509 (14) |
C4—O1 | 1.252 (3) | C11'—N2 | 1.546 (8) |
C4—O2 | 1.276 (3) | C11'—H11C | 0.9700 |
C4—C5 | 1.501 (4) | C11'—H11D | 0.9700 |
C5—C10 | 1.376 (4) | C12'—O3 | 1.362 (8) |
C5—C6 | 1.396 (4) | C12'—H12C | 0.9700 |
C6—C7 | 1.386 (4) | C12'—H12D | 0.9700 |
C6—H6 | 0.9300 | O3—C12'ii | 1.362 (8) |
C7—C8 | 1.369 (5) | O3—C12ii | 1.591 (10) |
C7—H7 | 0.9300 | O1W—H1A | 0.85 (4) |
C8—C9 | 1.380 (5) | ||
O2—Cu1—O2i | 180.0 | C12—C11—H11B | 111.5 |
O2—Cu1—N1 | 89.37 (9) | N2—C11—H11B | 111.5 |
O2i—Cu1—N1 | 90.63 (9) | H11A—C11—H11B | 109.3 |
O2—Cu1—N1i | 90.63 (9) | C11—C12—O3 | 105.8 (8) |
O2i—Cu1—N1i | 89.37 (9) | C11—C12—H12A | 110.6 |
N1—Cu1—N1i | 180.0 | O3—C12—H12A | 110.6 |
N1—C1—N2 | 112.0 (3) | C11—C12—H12B | 110.6 |
N1—C1—H1 | 124.0 | O3—C12—H12B | 110.6 |
N2—C1—H1 | 124.0 | H12A—C12—H12B | 108.7 |
C3—C2—N2 | 105.8 (3) | C12'—C11'—N2 | 109.7 (7) |
C3—C2—H2 | 127.1 | C12'—C11'—H11C | 109.7 |
N2—C2—H2 | 127.1 | N2—C11'—H11C | 109.7 |
C2—C3—N1 | 110.6 (3) | C12'—C11'—H11D | 109.7 |
C2—C3—H3 | 124.7 | N2—C11'—H11D | 109.7 |
N1—C3—H3 | 124.7 | H11C—C11'—H11D | 108.2 |
O1—C4—O2 | 122.9 (3) | O3—C12'—C11' | 104.5 (7) |
O1—C4—C5 | 120.6 (3) | O3—C12'—C12'ii | 46.1 (4) |
O2—C4—C5 | 116.5 (3) | C11'—C12'—C12'ii | 149.4 (6) |
C10—C5—C6 | 119.1 (3) | O3—C12'—H12C | 110.9 |
C10—C5—C4 | 121.0 (3) | C11'—C12'—H12C | 110.9 |
C6—C5—C4 | 120.0 (3) | C12'ii—C12'—H12C | 79.7 |
C7—C6—C5 | 119.8 (3) | O3—C12'—H12D | 110.9 |
C7—C6—H6 | 120.1 | C11'—C12'—H12D | 110.9 |
C5—C6—H6 | 120.1 | C12'ii—C12'—H12D | 91.2 |
C8—C7—C6 | 120.6 (3) | H12C—C12'—H12D | 108.9 |
C8—C7—H7 | 119.7 | C1—N1—C3 | 104.5 (3) |
C6—C7—H7 | 119.7 | C1—N1—Cu1 | 127.1 (2) |
C7—C8—C9 | 120.0 (3) | C3—N1—Cu1 | 127.8 (2) |
C7—C8—H8 | 120.0 | C1—N2—C2 | 107.0 (3) |
C9—C8—H8 | 120.0 | C1—N2—C11 | 133.1 (4) |
C8—C9—C10 | 119.8 (3) | C2—N2—C11 | 115.7 (4) |
C8—C9—H9 | 120.1 | C1—N2—C11' | 121.5 (4) |
C10—C9—H9 | 120.1 | C2—N2—C11' | 127.7 (4) |
C5—C10—C9 | 120.7 (3) | C4—O2—Cu1 | 108.55 (18) |
C5—C10—H10 | 119.7 | C12'ii—O3—C12' | 87.8 (7) |
C9—C10—H10 | 119.7 | C12'—O3—C12ii | 114.1 (8) |
C12—C11—N2 | 101.3 (8) | C12'ii—O3—C12 | 114.1 (8) |
C12—C11—H11A | 111.5 | C12ii—O3—C12 | 148.0 (9) |
N2—C11—H11A | 111.5 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O1iii | 0.85 (4) | 2.08 (5) | 2.862 (3) | 153 (4) |
Symmetry code: (iii) −x+1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C7H5O2)2(C10H14N4O)]·H2O |
Mr | 530.04 |
Crystal system, space group | Monoclinic, P2/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.4960 (15), 7.7400 (16), 13.609 (3) |
β (°) | 103.140 (3) |
V (Å3) | 1179.2 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.97 |
Crystal size (mm) | 0.11 × 0.11 × 0.10 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.901, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10769, 2697, 1980 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.123, 1.10 |
No. of reflections | 2697 |
No. of parameters | 183 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.44, −0.51 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O1i | 0.85 (4) | 2.08 (5) | 2.862 (3) | 153 (4) |
Symmetry code: (i) −x+1/2, y, −z+1/2. |
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The design and synthesis of coordination polymers has received much attention due to their interesting structures and potential applications in ion exchange and gas storage (Yang, Yue et al., 2006). In this regard, chain structures are particularly interesting (Yang et al., 2007). We selected 2,2'-bis(imidazol)ether (BIE) as a bridging ligand, generating a new chain coordination polymer, {[Cu(BA)2(BIE)].H2O}n, whose structure is reported here.
In the title compound, the copper(II) atom, which lies on an inversion centre, displays a square-planar coordination geometry provided by two nitrogen atoms from two BIE ligands and two oxygen atoms from two distinct benzoate anions (Fig. 1). The Cu—O and Cu—N distances (Cu1—N1 = 1.985 (2) Å, Cu1–O2 = 1.968 (2) Å) are within their normal ranges (Yang, Ma et al., 2006). The copper(II) centers are linked via BIE ligands to form a one-dimensional chain structure along the c axis (Fig. 2). The monodentate BA anions are located on both sides of the chain. The adjacent chains are further connected through hydrogen bonds between BA anions and water molecules (Table 2), thus forming a two-dimensional supramolecular network (Fig. 3). The ether (O3) and water (O1W) oxygen atoms lie on twofold axes. The C11, C12 carbon atom and attached H atoms are disordered over two positions with refined occupancies of 0.583 (12) and 0.417 (12).