The title complex, [Cu
2(C
7H
4FO
2)
4(C
2H
6O)
2], has a dimeric structure with two Cu
II atoms coordinated by four 4-fluorobenzoate groups and two ethanol molecules. The crystal packing is stabilized by intermolecular O—H
O hydrogen bonds.
Supporting information
CCDC reference: 245137
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.101
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1
PLAT432_ALERT_2_B Short Inter X...Y Contact C16' .. C16' .. 2.99 Ang.
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.19 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O2
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O4
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C15
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Cu1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O5
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 46
CU1 -CU1 -O5 -C15 -167.90 1.60 7.556 1.555 1.555 1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
10 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
8 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Crystal data top
[Cu2(C7H4FO2)4(C2H6O)2] | F(000) = 1576 |
Mr = 775.62 | Dx = 1.578 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.489 (4) Å | Cell parameters from 3353 reflections |
b = 6.629 (1) Å | θ = 4–27° |
c = 22.027 (4) Å | µ = 1.38 mm−1 |
β = 96.30 (3)° | T = 293 K |
V = 3263.9 (10) Å3 | Plate, blue |
Z = 4 | 0.20 × 0.20 × 0.02 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3353 independent reflections |
Radiation source: fine-focus sealed tube | 2418 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −28→28 |
Tmin = 0.770, Tmax = 0.973 | k = −8→4 |
7200 measured reflections | l = −27→27 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3 |
3353 reflections | (Δ/σ)max = 0.002 |
217 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.41 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 | Occ. (<1) |
Cu1 | 0.216324 (17) | 0.09853 (6) | 0.510206 (17) | 0.03308 (14) | |
C1 | 0.10994 (15) | 0.5171 (5) | 0.40302 (15) | 0.0392 (8) | |
C2 | 0.05628 (17) | 0.4186 (6) | 0.39158 (19) | 0.0598 (11) | |
H2A | 0.0528 | 0.2828 | 0.4059 | 0.080* | |
C3 | 0.00775 (19) | 0.5119 (7) | 0.3593 (2) | 0.0747 (14) | |
H3A | −0.0298 | 0.4433 | 0.3507 | 0.080* | |
C4 | 0.01509 (18) | 0.7067 (7) | 0.33959 (18) | 0.0591 (11) | |
C5 | 0.06696 (17) | 0.8077 (6) | 0.34963 (16) | 0.0503 (10) | |
H5A | 0.0702 | 0.9421 | 0.3341 | 0.080* | |
C6 | 0.11559 (16) | 0.7117 (5) | 0.38200 (14) | 0.0420 (8) | |
H6A | 0.1531 | 0.7811 | 0.3902 | 0.080* | |
C7 | 0.16178 (15) | 0.4151 (5) | 0.43886 (14) | 0.0377 (8) | |
C8 | 0.20316 (14) | 0.5220 (5) | 0.65066 (14) | 0.0345 (8) | |
C9 | 0.22397 (15) | 0.7155 (5) | 0.66507 (14) | 0.0413 (8) | |
H9A | 0.2502 | 0.7813 | 0.6397 | 0.080* | |
C10 | 0.20599 (17) | 0.8130 (6) | 0.71529 (16) | 0.0485 (9) | |
H10A | 0.2203 | 0.9459 | 0.7264 | 0.080* | |
C11 | 0.16792 (18) | 0.7178 (6) | 0.74915 (16) | 0.0526 (10) | |
C12 | 0.14602 (17) | 0.5279 (6) | 0.73624 (16) | 0.0532 (10) | |
H12A | 0.1188 | 0.4654 | 0.7612 | 0.080* | |
C13 | 0.16401 (16) | 0.4299 (5) | 0.68610 (15) | 0.0436 (9) | |
H13A | 0.1497 | 0.2964 | 0.6758 | 0.080* | |
C14 | 0.22139 (14) | 0.4180 (5) | 0.59546 (14) | 0.0351 (8) | |
C15 | 0.1047 (2) | −0.1814 (8) | 0.5406 (3) | 0.0954 (16) | |
H15A | 0.0811 | −0.2096 | 0.5026 | 0.080* | 0.59 |
H15B | 0.1028 | −0.2991 | 0.5657 | 0.080* | 0.59 |
H15C | 0.0904 | −0.3107 | 0.5244 | 0.080* | 0.41 |
H15D | 0.1073 | −0.1918 | 0.5847 | 0.080* | 0.41 |
O1 | 0.21041 (11) | 0.5079 (4) | 0.44505 (11) | 0.0524 (7) | |
O2 | 0.15353 (10) | 0.2461 (4) | 0.46054 (12) | 0.0611 (8) | |
O3 | 0.25595 (11) | 0.5090 (4) | 0.56441 (10) | 0.0505 (7) | |
O4 | 0.20009 (12) | 0.2483 (4) | 0.58282 (11) | 0.0639 (8) | |
O5 | 0.16287 (10) | −0.1596 (3) | 0.52578 (10) | 0.0430 (6) | |
H1A | 0.1824 | −0.2775 | 0.5239 | 0.080* | |
F1 | −0.03249 (10) | 0.7982 (4) | 0.30810 (11) | 0.0861 (8) | |
F2 | 0.15049 (11) | 0.8142 (4) | 0.79841 (10) | 0.0835 (8) | |
C16 | 0.0812 (4) | −0.0452 (13) | 0.5761 (4) | 0.084 (2)* | 0.59 |
H16A | 0.0410 | −0.08347 | 0.5816 | 0.080* | 0.59 |
H16B | 0.0810 | 0.08500 | 0.5570 | 0.080* | 0.59 |
H16C | 0.1048 | −0.03958 | 0.6151 | 0.080* | 0.59 |
C16' | 0.0631 (7) | −0.050 (2) | 0.5241 (7) | 0.110 (5)* | 0.41 |
H16D | 0.0263 | −0.0918 | 0.5386 | 0.080* | 0.41 |
H16E | 0.0576 | −0.0405 | 0.4804 | 0.080* | 0.41 |
H16F | 0.0747 | 0.0793 | 0.5411 | 0.080* | 0.41 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0345 (2) | 0.0291 (2) | 0.0362 (2) | −0.00325 (19) | 0.00655 (16) | −0.00048 (19) |
C1 | 0.038 (2) | 0.040 (2) | 0.0399 (19) | 0.0011 (16) | 0.0031 (16) | 0.0000 (16) |
C2 | 0.046 (2) | 0.049 (2) | 0.081 (3) | −0.008 (2) | −0.006 (2) | 0.018 (2) |
C3 | 0.041 (3) | 0.076 (3) | 0.102 (4) | −0.012 (2) | −0.016 (2) | 0.016 (3) |
C4 | 0.042 (2) | 0.068 (3) | 0.066 (3) | 0.009 (2) | −0.003 (2) | 0.018 (2) |
C5 | 0.049 (2) | 0.047 (2) | 0.054 (2) | 0.008 (2) | 0.0047 (19) | 0.0092 (19) |
C6 | 0.041 (2) | 0.045 (2) | 0.0396 (19) | −0.0018 (17) | 0.0046 (16) | 0.0001 (17) |
C7 | 0.039 (2) | 0.039 (2) | 0.0356 (18) | 0.0062 (18) | 0.0070 (15) | −0.0033 (17) |
C8 | 0.0331 (19) | 0.0382 (19) | 0.0320 (17) | 0.0034 (15) | 0.0022 (14) | −0.0013 (15) |
C9 | 0.042 (2) | 0.043 (2) | 0.0394 (19) | −0.0043 (17) | 0.0066 (16) | −0.0032 (17) |
C10 | 0.056 (3) | 0.046 (2) | 0.044 (2) | −0.0007 (19) | 0.0042 (18) | −0.0147 (18) |
C11 | 0.060 (3) | 0.061 (3) | 0.038 (2) | 0.006 (2) | 0.0094 (19) | −0.014 (2) |
C12 | 0.051 (3) | 0.067 (3) | 0.044 (2) | −0.001 (2) | 0.0170 (19) | 0.000 (2) |
C13 | 0.044 (2) | 0.045 (2) | 0.042 (2) | −0.0026 (17) | 0.0072 (16) | −0.0025 (17) |
C14 | 0.037 (2) | 0.0335 (19) | 0.0348 (18) | 0.0010 (16) | 0.0023 (15) | −0.0019 (16) |
C15 | 0.068 (4) | 0.093 (4) | 0.133 (4) | 0.001 (3) | 0.043 (3) | 0.007 (4) |
O1 | 0.0429 (16) | 0.0419 (15) | 0.0679 (17) | −0.0092 (13) | −0.0140 (13) | 0.0146 (13) |
O2 | 0.0379 (15) | 0.0487 (16) | 0.094 (2) | −0.0075 (13) | −0.0064 (14) | 0.0326 (15) |
O3 | 0.0743 (19) | 0.0387 (14) | 0.0426 (14) | −0.0167 (13) | 0.0251 (13) | −0.0080 (12) |
O5 | 0.0383 (14) | 0.0347 (13) | 0.0573 (15) | −0.0064 (11) | 0.0113 (12) | 0.0052 (11) |
F1 | 0.0515 (16) | 0.100 (2) | 0.1022 (19) | 0.0132 (14) | −0.0132 (14) | 0.0341 (17) |
F2 | 0.102 (2) | 0.0911 (19) | 0.0637 (15) | −0.0016 (16) | 0.0370 (14) | −0.0313 (14) |
O4 | 0.082 (2) | 0.0502 (17) | 0.0670 (17) | −0.0303 (15) | 0.0429 (15) | −0.0261 (14) |
Geometric parameters (Å, º) top
Cu1—O4 | 1.951 (2) | C10—C11 | 1.352 (5) |
Cu1—O2 | 1.952 (2) | C10—H10A | 0.9600 |
Cu1—O3i | 1.955 (2) | C11—F2 | 1.354 (4) |
Cu1—O1i | 1.957 (2) | C11—C12 | 1.370 (5) |
Cu1—O5 | 2.141 (2) | C12—C13 | 1.380 (5) |
Cu1—Cu1i | 2.5843 (8) | C12—H12A | 0.9599 |
C1—C2 | 1.371 (5) | C13—H13A | 0.9599 |
C1—C6 | 1.381 (4) | C14—O4 | 1.242 (4) |
C1—C7 | 1.496 (4) | C14—O3 | 1.246 (4) |
C2—C3 | 1.382 (5) | C15—C16' | 1.301 (15) |
C2—H2A | 0.9600 | C15—C16 | 1.340 (9) |
C3—C4 | 1.378 (6) | C15—O5 | 1.391 (5) |
C3—H3A | 0.9599 | C15—H15A | 0.96 |
C4—C5 | 1.342 (5) | C15—H15B | 0.96 |
C4—F1 | 1.353 (4) | C15—H15C | 0.96 |
C5—C6 | 1.392 (4) | C15—H15D | 0.96 |
C5—H5A | 0.9599 | O1—Cu1i | 1.957 (2) |
C6—H6A | 0.9602 | O3—Cu1i | 1.955 (2) |
C7—O2 | 1.240 (4) | O5—H1A | 0.9000 |
C7—O1 | 1.249 (4) | C16—H16A | 0.96 |
C8—C13 | 1.381 (4) | C16—H16A | 0.96 |
C8—C9 | 1.390 (4) | C16—H16C | 0.96 |
C8—C14 | 1.494 (4) | C16'—H16D | 0.96 |
C9—C10 | 1.380 (4) | C16'—H16E | 0.96 |
C9—H9A | 0.9598 | C16'—H16F | 0.96 |
| | | |
O4—Cu1—O2 | 90.89 (12) | O1—C7—C1 | 117.2 (3) |
O4—Cu1—O3i | 168.63 (10) | C13—C8—C9 | 119.9 (3) |
O2—Cu1—O3i | 89.40 (11) | C13—C8—C14 | 120.3 (3) |
O4—Cu1—O1i | 89.63 (12) | C9—C8—C14 | 119.7 (3) |
O2—Cu1—O1i | 168.74 (10) | C10—C9—C8 | 119.6 (3) |
O3i—Cu1—O1i | 87.90 (11) | C10—C9—H9A | 120.4 |
O4—Cu1—O5 | 96.69 (9) | C8—C9—H9A | 119.9 |
O2—Cu1—O5 | 96.08 (9) | C11—C10—C9 | 118.9 (4) |
O3i—Cu1—O5 | 94.58 (9) | C11—C10—H10A | 120.2 |
O1i—Cu1—O5 | 95.02 (9) | C9—C10—H10A | 120.9 |
O4—Cu1—Cu1i | 85.02 (7) | C10—C11—F2 | 118.6 (4) |
O2—Cu1—Cu1i | 85.12 (7) | C10—C11—C12 | 123.3 (3) |
O3i—Cu1—Cu1i | 83.68 (7) | F2—C11—C12 | 118.1 (4) |
O1i—Cu1—Cu1i | 83.72 (7) | C11—C12—C13 | 117.9 (4) |
O5—Cu1—Cu1i | 177.88 (7) | C11—C12—H12A | 121.0 |
C2—C1—C6 | 119.7 (3) | C13—C12—H12A | 121.1 |
C2—C1—C7 | 120.1 (3) | C12—C13—C8 | 120.3 (3) |
C6—C1—C7 | 120.3 (3) | C12—C13—H13A | 120.2 |
C1—C2—C3 | 120.7 (4) | C8—C13—H13A | 119.5 |
C1—C2—H2A | 119.2 | O4—C14—O3 | 124.3 (3) |
C3—C2—H2A | 120.0 | O4—C14—C8 | 117.8 (3) |
C4—C3—C2 | 117.8 (4) | O3—C14—C8 | 117.8 (3) |
C4—C3—H3A | 121.0 | C16'—C15—O5 | 122.0 (8) |
C2—C3—H3A | 121.2 | C16—C15—O5 | 120.5 (6) |
C5—C4—F1 | 119.0 (4) | C16—C15—H15A | 115.2 |
C5—C4—C3 | 123.2 (4) | O5—C15—H15A | 105.0 |
F1—C4—C3 | 117.8 (4) | H15A—C15—H15B | 107 |
C4—C5—C6 | 118.4 (4) | C7—O1—Cu1i | 123.8 (2) |
C4—C5—H5A | 120.2 | C7—O2—Cu1 | 122.6 (2) |
C6—C5—H5A | 121.4 | C14—O3—Cu1i | 124.1 (2) |
C1—C6—C5 | 120.2 (3) | C15—O5—Cu1 | 132.9 (3) |
C1—C6—H6A | 119.7 | C15—O5—H1A | 113.5 |
C5—C6—H6A | 120.1 | Cu1—O5—H1A | 113.6 |
O2—C7—O1 | 124.7 (3) | C14—O4—Cu1 | 122.9 (2) |
O2—C7—C1 | 118.1 (3) | | |
| | | |
C6—C1—C2—C3 | −0.1 (6) | C9—C8—C14—O3 | 1.1 (5) |
C7—C1—C2—C3 | 179.1 (4) | O2—C7—O1—Cu1i | 0.7 (5) |
C1—C2—C3—C4 | −0.5 (7) | C1—C7—O1—Cu1i | −179.7 (2) |
C2—C3—C4—C5 | 0.8 (7) | O1—C7—O2—Cu1 | 1.3 (5) |
C2—C3—C4—F1 | −179.9 (4) | C1—C7—O2—Cu1 | −178.2 (2) |
F1—C4—C5—C6 | −179.9 (3) | O4—Cu1—O2—C7 | 83.0 (3) |
C3—C4—C5—C6 | −0.6 (7) | O3i—Cu1—O2—C7 | −85.7 (3) |
C2—C1—C6—C5 | 0.3 (5) | O1i—Cu1—O2—C7 | −9.6 (8) |
C7—C1—C6—C5 | −178.8 (3) | O5—Cu1—O2—C7 | 179.8 (3) |
C4—C5—C6—C1 | 0.0 (5) | Cu1i—Cu1—O2—C7 | −2.0 (3) |
C2—C1—C7—O2 | −4.2 (5) | O4—C14—O3—Cu1i | −0.3 (5) |
C6—C1—C7—O2 | 175.0 (3) | C8—C14—O3—Cu1i | −178.7 (2) |
C2—C1—C7—O1 | 176.2 (3) | C16'—C15—O5—Cu1 | 29.1 (11) |
C6—C1—C7—O1 | −4.6 (5) | C16—C15—O5—Cu1 | −33.5 (9) |
C13—C8—C9—C10 | 0.9 (5) | O4—Cu1—O5—C15 | 48.2 (4) |
C14—C8—C9—C10 | 178.5 (3) | O2—Cu1—O5—C15 | −43.4 (4) |
C8—C9—C10—C11 | −0.5 (5) | O3i—Cu1—O5—C15 | −133.3 (4) |
C9—C10—C11—F2 | 179.9 (3) | O1i—Cu1—O5—C15 | 138.5 (4) |
C9—C10—C11—C12 | 0.0 (6) | Cu1i—Cu1—O5—C15 | −167.9 (16) |
C10—C11—C12—C13 | 0.1 (6) | O3—C14—O4—Cu1 | −1.5 (5) |
F2—C11—C12—C13 | −179.8 (3) | C8—C14—O4—Cu1 | 176.9 (2) |
C11—C12—C13—C8 | 0.3 (5) | O2—Cu1—O4—C14 | −83.2 (3) |
C9—C8—C13—C12 | −0.8 (5) | O3i—Cu1—O4—C14 | 8.1 (8) |
C14—C8—C13—C12 | −178.4 (3) | O1i—Cu1—O4—C14 | 85.5 (3) |
C13—C8—C14—O4 | 0.2 (5) | O5—Cu1—O4—C14 | −179.5 (3) |
C9—C8—C14—O4 | −177.4 (3) | Cu1i—Cu1—O4—C14 | 1.8 (3) |
C13—C8—C14—O3 | 178.7 (3) | | |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H1A···O3ii | 0.90 | 2.28 | 3.089 (3) | 149 |
O5—H1A···O1ii | 0.90 | 2.38 | 3.095 (4) | 136 |
Symmetry code: (ii) x, y−1, z. |