Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056887/cv2347sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056887/cv2347Isup2.hkl |
CCDC reference: 672681
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.015 Å
- Disorder in main residue
- R factor = 0.076
- wR factor = 0.241
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.12 Sigma PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 8 Ang. 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 O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C30 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.56 PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C27 -C32 1.34 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 15 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O1 -CU1 -N1 -C15 -172.20 1.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 5 O1 -CU1 -N1 -C19 7.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 N1 -CU1 -O1 -C1 70.00 2.00 1.555 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 4.40 Deg. F1 -C3 -H3 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 6.20 Deg. F1' -C7 -H7 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 594
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 21 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The reaction was carried out by the solvothermal method. 2,3,4,5-tetrafluorobenzoic acid(0.386 g,2 mmol) and cupric acetate(0.199 g, 1 mmol) and 1,10-phenanthroline(0.180 g, 1 mmol) were added to the airtight vessel with 20 ml water. The resulting green solution was filtered. The filtrate was placed for sevaral days yielding green block-shaped crystals.
The yield is 81% and elemental analysis: calc. for C32H14CuF12N2O5: C 48.16, H 1.77, N 3.51; found: C 48.45, H 3.39, N 3.22. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.
All H atoms were geometrically positioned (C—H 0.93 Å, O—H 0.82 Å) and refined as riding, with Uiso(H)=1.2Ueq of the parent atom. Atom F1 was treated as statistically disordered bwteen two positions with the refined occupancies of 0.572 (7) and 0.428 (7), respectively.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.
Fig. 1. View of the title compound with the atomic numbering and 30% probability displacement ellipsoids. H atoms omitted for clarity. |
[Cu(C13H6F4O2)2(C12H8N2)(H2O)]·C6H2F4 | F(000) = 1588 |
Mr = 797.99 | Dx = 1.760 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8150 (8) Å | Cell parameters from 2282 reflections |
b = 28.9810 (16) Å | θ = 2.7–25.3° |
c = 15.44800 (8) Å | µ = 0.85 mm−1 |
β = 99.226 (2)° | T = 298 K |
V = 3011.6 (4) Å3 | Block, green |
Z = 4 | 0.37 × 0.15 × 0.14 mm |
CCD area detector diffractometer | 5137 independent reflections |
Radiation source: fine-focus sealed tube | 2352 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→6 |
Tmin = 0.745, Tmax = 0.891 | k = −26→34 |
14410 measured reflections | l = −18→17 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.076 | H-atom parameters constrained |
wR(F2) = 0.241 | w = 1/[σ2(Fo2) + (0.1138P)2 + 2.0328P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5137 reflections | Δρmax = 0.77 e Å−3 |
450 parameters | Δρmin = −0.68 e Å−3 |
594 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (8) |
[Cu(C13H6F4O2)2(C12H8N2)(H2O)]·C6H2F4 | V = 3011.6 (4) Å3 |
Mr = 797.99 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.8150 (8) Å | µ = 0.85 mm−1 |
b = 28.9810 (16) Å | T = 298 K |
c = 15.44800 (8) Å | 0.37 × 0.15 × 0.14 mm |
β = 99.226 (2)° |
CCD area detector diffractometer | 5137 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2352 reflections with I > 2σ(I) |
Tmin = 0.745, Tmax = 0.891 | Rint = 0.067 |
14410 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 594 restraints |
wR(F2) = 0.241 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.77 e Å−3 |
5137 reflections | Δρmin = −0.68 e Å−3 |
450 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 | 0.78922 (12) | 0.40017 (3) | 0.82641 (6) | 0.0500 (4) | |
F1 | 1.3110 (12) | 0.4545 (3) | 0.6146 (6) | 0.092 (2) | 0.572 (7) |
F1' | 0.6297 (16) | 0.4035 (4) | 0.5423 (8) | 0.092 (2) | 0.428 (7) |
F2 | 1.3111 (7) | 0.46696 (19) | 0.4451 (3) | 0.0910 (16) | |
F3 | 0.9875 (8) | 0.45009 (19) | 0.3259 (3) | 0.0962 (17) | |
F4 | 0.6523 (8) | 0.4203 (2) | 0.3754 (3) | 0.0969 (17) | |
F5 | 1.4666 (8) | 0.2934 (2) | 0.9151 (5) | 0.136 (3) | |
F6 | 1.5600 (9) | 0.2049 (2) | 0.9159 (6) | 0.160 (3) | |
F7 | 1.2794 (10) | 0.14033 (18) | 0.8663 (5) | 0.146 (3) | |
F8 | 0.8983 (9) | 0.16610 (18) | 0.8170 (5) | 0.129 (2) | |
F9 | 0.5918 (14) | 0.2803 (3) | 0.2011 (7) | 0.188 (2) | |
F10 | 0.2495 (13) | 0.3180 (2) | 0.1405 (6) | 0.173 (3) | |
F11 | −0.0500 (14) | 0.2650 (3) | 0.0694 (7) | 0.188 (2) | |
F12 | −0.0109 (15) | 0.1768 (3) | 0.0570 (8) | 0.225 (5) | |
N1 | 0.7820 (8) | 0.40042 (19) | 0.9543 (4) | 0.0516 (15) | |
N2 | 0.7463 (8) | 0.4693 (2) | 0.8454 (4) | 0.0520 (16) | |
O1 | 0.7985 (8) | 0.40807 (18) | 0.7036 (4) | 0.0688 (15) | |
O2 | 1.1109 (8) | 0.4300 (2) | 0.7359 (4) | 0.0768 (17) | |
O3 | 0.8838 (8) | 0.33670 (17) | 0.8284 (3) | 0.0617 (14) | |
O4 | 1.1788 (8) | 0.35633 (18) | 0.9038 (4) | 0.0701 (16) | |
O5 | 0.4629 (7) | 0.38446 (19) | 0.7994 (4) | 0.0707 (16) | |
H5A | 0.3958 | 0.4073 | 0.7765 | 0.085* | |
H5B | 0.4205 | 0.3765 | 0.8460 | 0.085* | |
C1 | 0.9584 (12) | 0.4212 (3) | 0.6839 (5) | 0.0525 (17) | |
C2 | 0.9670 (11) | 0.4291 (2) | 0.5874 (5) | 0.0507 (17) | |
C3 | 1.1382 (11) | 0.4449 (2) | 0.5596 (5) | 0.0561 (18) | |
H3 | 1.2503 | 0.4513 | 0.6006 | 0.067* | 0.428 (7) |
C4 | 1.1439 (12) | 0.4510 (3) | 0.4727 (6) | 0.0600 (19) | |
C5 | 0.9808 (13) | 0.4434 (3) | 0.4121 (5) | 0.063 (2) | |
C6 | 0.8114 (12) | 0.4276 (3) | 0.4375 (6) | 0.0628 (19) | |
C7 | 0.8020 (11) | 0.4210 (3) | 0.5250 (5) | 0.0573 (18) | |
H7 | 0.6841 | 0.4111 | 0.5421 | 0.069* | 0.572 (7) |
C8 | 1.0611 (12) | 0.3282 (3) | 0.8664 (6) | 0.0578 (19) | |
C9 | 1.1242 (11) | 0.2780 (3) | 0.8655 (6) | 0.065 (2) | |
C10 | 1.3182 (13) | 0.2639 (3) | 0.8900 (7) | 0.076 (2) | |
C11 | 1.3644 (14) | 0.2171 (3) | 0.8885 (7) | 0.088 (3) | |
C12 | 1.2302 (15) | 0.1857 (3) | 0.8678 (7) | 0.084 (2) | |
C13 | 1.0365 (15) | 0.1984 (3) | 0.8409 (7) | 0.086 (2) | |
C14 | 0.9808 (14) | 0.2456 (3) | 0.8398 (6) | 0.077 (2) | |
H14 | 0.8493 | 0.2544 | 0.8218 | 0.093* | |
C15 | 0.7900 (11) | 0.3644 (3) | 1.0091 (5) | 0.0626 (19) | |
H15 | 0.7997 | 0.3347 | 0.9872 | 0.075* | |
C16 | 0.7840 (12) | 0.3702 (3) | 1.0981 (6) | 0.072 (2) | |
H16 | 0.7858 | 0.3441 | 1.1334 | 0.086* | |
C17 | 0.7758 (12) | 0.4119 (3) | 1.1349 (6) | 0.068 (2) | |
H17 | 0.7750 | 0.4151 | 1.1947 | 0.082* | |
C18 | 0.7686 (10) | 0.4502 (3) | 1.0802 (5) | 0.0543 (17) | |
C19 | 0.7699 (10) | 0.4428 (3) | 0.9901 (5) | 0.0529 (17) | |
C20 | 0.7507 (10) | 0.4802 (3) | 0.9295 (6) | 0.0531 (17) | |
C21 | 0.7379 (10) | 0.5253 (3) | 0.9603 (6) | 0.0590 (18) | |
C22 | 0.7192 (11) | 0.5600 (3) | 0.8973 (7) | 0.067 (2) | |
H22 | 0.7150 | 0.5907 | 0.9142 | 0.081* | |
C23 | 0.7073 (12) | 0.5493 (3) | 0.8130 (7) | 0.071 (2) | |
H23 | 0.6892 | 0.5724 | 0.7708 | 0.086* | |
C24 | 0.7222 (11) | 0.5028 (3) | 0.7875 (6) | 0.064 (2) | |
H24 | 0.7148 | 0.4957 | 0.7284 | 0.077* | |
C25 | 0.7577 (11) | 0.4964 (3) | 1.1095 (6) | 0.066 (2) | |
H25 | 0.7590 | 0.5020 | 1.1689 | 0.079* | |
C26 | 0.7457 (10) | 0.5319 (3) | 1.0539 (6) | 0.0634 (19) | |
H26 | 0.7423 | 0.5617 | 1.0758 | 0.076* | |
C27 | 0.451 (3) | 0.2499 (7) | 0.1628 (13) | 0.188 (2) | |
C28 | 0.278 (3) | 0.2712 (5) | 0.1346 (12) | 0.173 (3) | |
C29 | 0.132 (3) | 0.2465 (7) | 0.1038 (13) | 0.188 (2) | |
C30 | 0.151 (3) | 0.1996 (5) | 0.0959 (11) | 0.163 (4) | |
C31 | 0.328 (3) | 0.1800 (5) | 0.1200 (11) | 0.165 (4) | |
H31 | 0.3432 | 0.1487 | 0.1101 | 0.198* | |
C32 | 0.486 (2) | 0.2046 (5) | 0.1583 (11) | 0.162 (4) | |
H32 | 0.6083 | 0.1913 | 0.1796 | 0.195* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0465 (6) | 0.0506 (6) | 0.0529 (6) | 0.0004 (4) | 0.0082 (4) | −0.0032 (4) |
F1 | 0.061 (4) | 0.131 (6) | 0.082 (5) | −0.011 (4) | 0.007 (4) | 0.000 (5) |
F1' | 0.061 (4) | 0.131 (6) | 0.082 (5) | −0.011 (4) | 0.007 (4) | 0.000 (5) |
F2 | 0.085 (3) | 0.111 (4) | 0.086 (4) | −0.003 (3) | 0.040 (3) | 0.016 (3) |
F3 | 0.109 (4) | 0.128 (5) | 0.057 (3) | 0.007 (3) | 0.028 (3) | 0.008 (3) |
F4 | 0.085 (4) | 0.138 (5) | 0.059 (3) | −0.011 (3) | −0.014 (3) | −0.002 (3) |
F5 | 0.062 (3) | 0.079 (4) | 0.264 (9) | −0.010 (3) | 0.015 (4) | 0.010 (4) |
F6 | 0.082 (4) | 0.106 (5) | 0.293 (10) | 0.041 (4) | 0.035 (5) | 0.038 (5) |
F7 | 0.157 (6) | 0.056 (3) | 0.238 (9) | 0.043 (4) | 0.070 (6) | 0.008 (4) |
F8 | 0.123 (5) | 0.053 (3) | 0.201 (7) | −0.014 (3) | −0.005 (5) | −0.028 (4) |
F9 | 0.184 (5) | 0.148 (4) | 0.213 (5) | −0.018 (4) | −0.025 (4) | 0.040 (4) |
F10 | 0.218 (6) | 0.085 (4) | 0.200 (6) | 0.006 (4) | −0.014 (5) | 0.017 (4) |
F11 | 0.184 (5) | 0.148 (4) | 0.213 (5) | −0.018 (4) | −0.025 (4) | 0.040 (4) |
F12 | 0.206 (9) | 0.136 (7) | 0.302 (14) | −0.052 (6) | −0.055 (9) | 0.038 (7) |
N1 | 0.040 (3) | 0.035 (3) | 0.079 (5) | 0.006 (3) | 0.007 (3) | 0.001 (3) |
N2 | 0.037 (3) | 0.059 (4) | 0.061 (4) | −0.002 (3) | 0.012 (3) | 0.017 (3) |
O1 | 0.053 (3) | 0.082 (4) | 0.075 (4) | −0.005 (3) | 0.020 (3) | −0.007 (3) |
O2 | 0.066 (4) | 0.108 (5) | 0.052 (4) | 0.007 (3) | −0.006 (3) | −0.005 (3) |
O3 | 0.059 (3) | 0.062 (3) | 0.065 (4) | −0.001 (3) | 0.013 (3) | −0.005 (3) |
O4 | 0.060 (3) | 0.053 (3) | 0.097 (5) | −0.008 (3) | 0.011 (3) | −0.009 (3) |
O5 | 0.044 (3) | 0.084 (4) | 0.086 (4) | −0.004 (3) | 0.014 (3) | 0.001 (3) |
C1 | 0.052 (4) | 0.058 (4) | 0.047 (4) | 0.011 (3) | 0.006 (4) | 0.002 (3) |
C2 | 0.051 (4) | 0.056 (4) | 0.047 (4) | 0.003 (3) | 0.011 (3) | 0.000 (3) |
C3 | 0.050 (4) | 0.058 (4) | 0.059 (4) | 0.005 (3) | 0.006 (4) | −0.001 (4) |
C4 | 0.056 (4) | 0.064 (4) | 0.063 (5) | 0.001 (4) | 0.020 (4) | 0.002 (4) |
C5 | 0.073 (5) | 0.076 (5) | 0.042 (4) | 0.000 (4) | 0.014 (4) | 0.000 (4) |
C6 | 0.063 (4) | 0.071 (5) | 0.054 (4) | −0.005 (4) | 0.008 (4) | −0.001 (4) |
C7 | 0.053 (4) | 0.070 (4) | 0.051 (4) | −0.007 (4) | 0.016 (4) | −0.001 (4) |
C8 | 0.055 (4) | 0.048 (4) | 0.075 (5) | −0.007 (4) | 0.021 (4) | 0.001 (4) |
C9 | 0.050 (4) | 0.051 (4) | 0.097 (6) | −0.001 (3) | 0.023 (4) | 0.000 (4) |
C10 | 0.059 (5) | 0.058 (4) | 0.112 (6) | 0.001 (4) | 0.016 (4) | 0.001 (4) |
C11 | 0.070 (5) | 0.076 (5) | 0.120 (7) | 0.014 (5) | 0.021 (5) | 0.009 (5) |
C12 | 0.083 (5) | 0.049 (5) | 0.121 (6) | 0.006 (4) | 0.025 (5) | 0.004 (5) |
C13 | 0.084 (5) | 0.059 (5) | 0.113 (6) | −0.002 (5) | 0.008 (5) | −0.004 (5) |
C14 | 0.075 (5) | 0.053 (4) | 0.104 (6) | −0.004 (4) | 0.012 (4) | −0.012 (4) |
C15 | 0.056 (4) | 0.062 (4) | 0.070 (5) | 0.006 (4) | 0.012 (4) | −0.004 (4) |
C16 | 0.062 (4) | 0.089 (5) | 0.063 (5) | 0.001 (4) | 0.010 (4) | 0.017 (4) |
C17 | 0.058 (4) | 0.086 (5) | 0.059 (4) | −0.004 (4) | 0.001 (4) | −0.007 (4) |
C18 | 0.033 (3) | 0.068 (4) | 0.061 (4) | −0.004 (3) | 0.007 (3) | −0.012 (4) |
C19 | 0.032 (3) | 0.061 (4) | 0.065 (4) | −0.005 (3) | 0.005 (3) | −0.008 (3) |
C20 | 0.033 (3) | 0.055 (4) | 0.074 (4) | −0.003 (3) | 0.017 (3) | −0.013 (3) |
C21 | 0.033 (3) | 0.061 (4) | 0.084 (5) | −0.008 (3) | 0.013 (3) | −0.015 (4) |
C22 | 0.048 (4) | 0.055 (4) | 0.100 (5) | 0.002 (3) | 0.015 (4) | −0.001 (4) |
C23 | 0.055 (4) | 0.061 (5) | 0.101 (6) | −0.001 (4) | 0.021 (4) | 0.012 (4) |
C24 | 0.056 (4) | 0.063 (4) | 0.076 (5) | 0.001 (4) | 0.019 (4) | 0.008 (4) |
C25 | 0.042 (4) | 0.081 (5) | 0.073 (5) | −0.003 (4) | 0.007 (4) | −0.020 (4) |
C26 | 0.039 (4) | 0.065 (4) | 0.085 (5) | −0.004 (3) | 0.008 (4) | −0.027 (4) |
C27 | 0.184 (5) | 0.148 (4) | 0.213 (5) | −0.018 (4) | −0.025 (4) | 0.040 (4) |
C28 | 0.218 (6) | 0.085 (4) | 0.200 (6) | 0.006 (4) | −0.014 (5) | 0.017 (4) |
C29 | 0.184 (5) | 0.148 (4) | 0.213 (5) | −0.018 (4) | −0.025 (4) | 0.040 (4) |
C30 | 0.174 (9) | 0.105 (7) | 0.195 (9) | −0.017 (7) | −0.017 (8) | 0.043 (7) |
C31 | 0.179 (9) | 0.105 (7) | 0.195 (9) | 0.000 (7) | −0.021 (8) | 0.040 (7) |
C32 | 0.170 (8) | 0.110 (7) | 0.191 (9) | 0.004 (7) | −0.021 (8) | 0.043 (7) |
Cu1—O1 | 1.922 (6) | C8—C9 | 1.517 (10) |
Cu1—O3 | 1.948 (5) | C9—C14 | 1.367 (11) |
Cu1—N1 | 1.985 (6) | C9—C10 | 1.378 (11) |
Cu1—N2 | 2.052 (6) | C10—C11 | 1.393 (12) |
Cu1—O5 | 2.243 (5) | C11—C12 | 1.294 (12) |
F1—C3 | 1.366 (11) | C12—C13 | 1.369 (12) |
F1'—C7 | 1.345 (13) | C13—C14 | 1.421 (11) |
F2—C4 | 1.360 (8) | C14—H14 | 0.9300 |
F3—C5 | 1.354 (8) | C15—C16 | 1.391 (11) |
F4—C6 | 1.345 (9) | C15—H15 | 0.9300 |
F5—C10 | 1.332 (9) | C16—C17 | 1.341 (11) |
F6—C11 | 1.379 (10) | C16—H16 | 0.9300 |
F7—C12 | 1.358 (9) | C17—C18 | 1.391 (11) |
F8—C13 | 1.336 (10) | C17—H17 | 0.9300 |
F9—C27 | 1.368 (17) | C18—C19 | 1.410 (10) |
F10—C28 | 1.373 (15) | C18—C25 | 1.418 (10) |
F11—C29 | 1.378 (18) | C19—C20 | 1.425 (10) |
F12—C30 | 1.343 (17) | C20—C21 | 1.399 (10) |
N1—C15 | 1.340 (9) | C21—C22 | 1.390 (11) |
N1—C19 | 1.354 (9) | C21—C26 | 1.450 (11) |
N2—C24 | 1.312 (9) | C22—C23 | 1.329 (11) |
N2—C20 | 1.333 (9) | C22—H22 | 0.9300 |
O1—C1 | 1.238 (9) | C23—C24 | 1.412 (11) |
O2—C1 | 1.234 (9) | C23—H23 | 0.9300 |
O3—C8 | 1.280 (9) | C24—H24 | 0.9300 |
O4—C8 | 1.222 (9) | C25—C26 | 1.335 (11) |
O5—H5A | 0.8501 | C25—H25 | 0.9300 |
O5—H5B | 0.8499 | C26—H26 | 0.9300 |
C1—C2 | 1.520 (10) | C27—C32 | 1.34 (2) |
C2—C7 | 1.378 (10) | C27—C28 | 1.34 (2) |
C2—C3 | 1.384 (10) | C28—C29 | 1.25 (2) |
C3—C4 | 1.361 (10) | C29—C30 | 1.37 (2) |
C3—H3 | 0.9300 | C30—C31 | 1.334 (19) |
C4—C5 | 1.352 (11) | C31—C32 | 1.344 (18) |
C5—C6 | 1.357 (11) | C31—H31 | 0.9300 |
C6—C7 | 1.377 (10) | C32—H32 | 0.9300 |
C7—H7 | 0.9300 | ||
O1—Cu1—O3 | 93.7 (2) | F7—C12—C13 | 118.9 (9) |
O1—Cu1—N1 | 172.9 (2) | F8—C13—C12 | 119.9 (8) |
O3—Cu1—N1 | 92.8 (2) | F8—C13—C14 | 119.7 (8) |
O1—Cu1—N2 | 93.0 (2) | C12—C13—C14 | 120.3 (9) |
O3—Cu1—N2 | 166.9 (2) | C9—C14—C13 | 118.8 (9) |
N1—Cu1—N2 | 80.0 (2) | C9—C14—H14 | 120.6 |
O1—Cu1—O5 | 91.7 (2) | C13—C14—H14 | 120.6 |
O3—Cu1—O5 | 97.3 (2) | N1—C15—C16 | 121.6 (8) |
N1—Cu1—O5 | 90.2 (2) | N1—C15—H15 | 119.2 |
N2—Cu1—O5 | 93.7 (2) | C16—C15—H15 | 119.2 |
C15—N1—C19 | 116.6 (7) | C17—C16—C15 | 122.5 (8) |
C15—N1—Cu1 | 128.4 (5) | C17—C16—H16 | 118.7 |
C19—N1—Cu1 | 115.0 (5) | C15—C16—H16 | 118.7 |
C24—N2—C20 | 117.9 (7) | C16—C17—C18 | 117.5 (8) |
C24—N2—Cu1 | 129.0 (6) | C16—C17—H17 | 121.3 |
C20—N2—Cu1 | 113.0 (5) | C18—C17—H17 | 121.3 |
C1—O1—Cu1 | 116.7 (5) | C17—C18—C19 | 118.2 (7) |
C8—O3—Cu1 | 118.3 (5) | C17—C18—C25 | 123.8 (8) |
Cu1—O5—H5A | 111.7 | C19—C18—C25 | 117.9 (8) |
Cu1—O5—H5B | 111.0 | N1—C19—C18 | 123.5 (7) |
H5A—O5—H5B | 109.3 | N1—C19—C20 | 115.3 (7) |
O2—C1—O1 | 125.9 (8) | C18—C19—C20 | 121.2 (7) |
O2—C1—C2 | 116.5 (7) | N2—C20—C21 | 124.2 (8) |
O1—C1—C2 | 117.5 (7) | N2—C20—C19 | 116.4 (7) |
C7—C2—C3 | 118.2 (7) | C21—C20—C19 | 119.5 (8) |
C7—C2—C1 | 120.3 (7) | C22—C21—C20 | 116.1 (8) |
C3—C2—C1 | 121.4 (7) | C22—C21—C26 | 126.0 (8) |
C4—C3—F1 | 115.4 (8) | C20—C21—C26 | 117.9 (8) |
C4—C3—C2 | 120.5 (8) | C23—C22—C21 | 120.1 (8) |
F1—C3—C2 | 124.0 (8) | C23—C22—H22 | 119.9 |
C4—C3—H3 | 119.7 | C21—C22—H22 | 119.9 |
F1—C3—H3 | 4.4 | C22—C23—C24 | 120.0 (9) |
C2—C3—H3 | 119.7 | C22—C23—H23 | 120.0 |
C5—C4—F2 | 118.4 (7) | C24—C23—H23 | 120.0 |
C5—C4—C3 | 120.8 (7) | N2—C24—C23 | 121.5 (9) |
F2—C4—C3 | 120.8 (8) | N2—C24—H24 | 119.2 |
C4—C5—F3 | 120.3 (7) | C23—C24—H24 | 119.2 |
C4—C5—C6 | 119.8 (8) | C26—C25—C18 | 121.5 (8) |
F3—C5—C6 | 119.8 (8) | C26—C25—H25 | 119.3 |
F4—C6—C5 | 118.3 (8) | C18—C25—H25 | 119.3 |
F4—C6—C7 | 121.2 (7) | C25—C26—C21 | 121.9 (8) |
C5—C6—C7 | 120.5 (8) | C25—C26—H26 | 119.0 |
F1'—C7—C6 | 115.2 (9) | C21—C26—H26 | 119.0 |
F1'—C7—C2 | 124.5 (8) | C32—C27—C28 | 126.3 (19) |
C6—C7—C2 | 120.1 (7) | C32—C27—F9 | 122.4 (18) |
F1'—C7—H7 | 6.2 | C28—C27—F9 | 111.3 (19) |
C6—C7—H7 | 120.0 | C29—C28—C27 | 117.3 (18) |
C2—C7—H7 | 120.0 | C29—C28—F10 | 119 (2) |
O4—C8—O3 | 126.1 (7) | C27—C28—F10 | 124.0 (19) |
O4—C8—C9 | 118.6 (8) | C28—C29—C30 | 121 (2) |
O3—C8—C9 | 115.4 (7) | C28—C29—F11 | 122.2 (19) |
C14—C9—C10 | 119.1 (8) | C30—C29—F11 | 116.1 (17) |
C14—C9—C8 | 118.1 (7) | C31—C30—F12 | 123.8 (16) |
C10—C9—C8 | 122.8 (7) | C31—C30—C29 | 119.3 (18) |
F5—C10—C9 | 122.7 (7) | F12—C30—C29 | 116.6 (17) |
F5—C10—C11 | 117.7 (8) | C30—C31—C32 | 121.4 (17) |
C9—C10—C11 | 119.5 (8) | C30—C31—H31 | 119.3 |
C12—C11—F6 | 120.3 (9) | C32—C31—H31 | 119.3 |
C12—C11—C10 | 122.5 (9) | C27—C32—C31 | 113.9 (17) |
F6—C11—C10 | 117.1 (9) | C27—C32—H32 | 123.1 |
C11—C12—F7 | 121.3 (9) | C31—C32—H32 | 123.1 |
C11—C12—C13 | 119.7 (9) | ||
O1—Cu1—N1—C15 | −172.2 (16) | C9—C10—C11—F6 | −178.3 (9) |
O3—Cu1—N1—C15 | −15.0 (6) | F6—C11—C12—F7 | −4.8 (17) |
N2—Cu1—N1—C15 | 176.1 (6) | C10—C11—C12—F7 | 179.6 (10) |
O5—Cu1—N1—C15 | 82.3 (6) | F6—C11—C12—C13 | 179.8 (10) |
O1—Cu1—N1—C19 | 7 (2) | C10—C11—C12—C13 | 4.2 (17) |
O3—Cu1—N1—C19 | 164.1 (5) | C11—C12—C13—F8 | 178.0 (10) |
N2—Cu1—N1—C19 | −4.8 (4) | F7—C12—C13—F8 | 2.5 (16) |
O5—Cu1—N1—C19 | −98.6 (5) | C11—C12—C13—C14 | −3.1 (17) |
O1—Cu1—N2—C24 | 4.0 (6) | F7—C12—C13—C14 | −178.6 (9) |
O3—Cu1—N2—C24 | 124.9 (10) | C10—C9—C14—C13 | 1.3 (14) |
N1—Cu1—N2—C24 | −177.4 (6) | C8—C9—C14—C13 | −178.3 (8) |
O5—Cu1—N2—C24 | −87.8 (6) | F8—C13—C14—C9 | 179.2 (9) |
O1—Cu1—N2—C20 | −173.7 (5) | C12—C13—C14—C9 | 0.3 (15) |
O3—Cu1—N2—C20 | −52.8 (11) | C19—N1—C15—C16 | 0.6 (10) |
N1—Cu1—N2—C20 | 4.9 (4) | Cu1—N1—C15—C16 | 179.7 (5) |
O5—Cu1—N2—C20 | 94.4 (5) | N1—C15—C16—C17 | −2.0 (12) |
O3—Cu1—O1—C1 | −87.6 (5) | C15—C16—C17—C18 | 1.5 (12) |
N1—Cu1—O1—C1 | 70 (2) | C16—C17—C18—C19 | 0.1 (11) |
N2—Cu1—O1—C1 | 81.1 (5) | C16—C17—C18—C25 | 179.4 (7) |
O5—Cu1—O1—C1 | 174.9 (5) | C15—N1—C19—C18 | 1.0 (10) |
O1—Cu1—O3—C8 | 107.7 (5) | Cu1—N1—C19—C18 | −178.2 (5) |
N1—Cu1—O3—C8 | −69.6 (6) | C15—N1—C19—C20 | −176.7 (6) |
N2—Cu1—O3—C8 | −13.1 (13) | Cu1—N1—C19—C20 | 4.1 (7) |
O5—Cu1—O3—C8 | −160.1 (5) | C17—C18—C19—N1 | −1.4 (10) |
Cu1—O1—C1—O2 | −0.6 (10) | C25—C18—C19—N1 | 179.2 (6) |
Cu1—O1—C1—C2 | −178.2 (5) | C17—C18—C19—C20 | 176.2 (6) |
O2—C1—C2—C7 | −178.7 (7) | C25—C18—C19—C20 | −3.1 (10) |
O1—C1—C2—C7 | −0.9 (11) | C24—N2—C20—C21 | −2.2 (10) |
O2—C1—C2—C3 | 0.6 (10) | Cu1—N2—C20—C21 | 175.8 (5) |
O1—C1—C2—C3 | 178.4 (7) | C24—N2—C20—C19 | 177.8 (6) |
C7—C2—C3—C4 | −1.7 (11) | Cu1—N2—C20—C19 | −4.2 (7) |
C1—C2—C3—C4 | 179.0 (7) | N1—C19—C20—N2 | 0.2 (9) |
C7—C2—C3—F1 | 179.5 (8) | C18—C19—C20—N2 | −177.6 (6) |
C1—C2—C3—F1 | 0.2 (12) | N1—C19—C20—C21 | −179.8 (6) |
F1—C3—C4—C5 | −178.8 (8) | C18—C19—C20—C21 | 2.4 (10) |
C2—C3—C4—C5 | 2.3 (12) | N2—C20—C21—C22 | 0.1 (10) |
F1—C3—C4—F2 | −1.8 (11) | C19—C20—C21—C22 | −179.9 (6) |
C2—C3—C4—F2 | 179.4 (7) | N2—C20—C21—C26 | −179.7 (6) |
F2—C4—C5—F3 | 2.2 (12) | C19—C20—C21—C26 | 0.3 (9) |
C3—C4—C5—F3 | 179.3 (7) | C20—C21—C22—C23 | 2.4 (11) |
F2—C4—C5—C6 | −179.8 (7) | C26—C21—C22—C23 | −177.8 (7) |
C3—C4—C5—C6 | −2.7 (12) | C21—C22—C23—C24 | −2.7 (12) |
C4—C5—C6—F4 | −179.7 (7) | C20—N2—C24—C23 | 1.9 (10) |
F3—C5—C6—F4 | −1.7 (12) | Cu1—N2—C24—C23 | −175.8 (5) |
C4—C5—C6—C7 | 2.5 (13) | C22—C23—C24—N2 | 0.5 (12) |
F3—C5—C6—C7 | −179.5 (7) | C17—C18—C25—C26 | −178.2 (7) |
F4—C6—C7—F1' | 5.0 (13) | C19—C18—C25—C26 | 1.1 (11) |
C5—C6—C7—F1' | −177.3 (9) | C18—C25—C26—C21 | 1.6 (11) |
F4—C6—C7—C2 | −179.7 (7) | C22—C21—C26—C25 | 177.9 (7) |
C5—C6—C7—C2 | −2.0 (12) | C20—C21—C26—C25 | −2.3 (10) |
C3—C2—C7—F1' | 176.5 (9) | C32—C27—C28—C29 | 3 (4) |
C1—C2—C7—F1' | −4.2 (13) | F9—C27—C28—C29 | −175.1 (18) |
C3—C2—C7—C6 | 1.5 (11) | C32—C27—C28—F10 | −179.7 (16) |
C1—C2—C7—C6 | −179.2 (7) | F9—C27—C28—F10 | 2 (3) |
Cu1—O3—C8—O4 | 1.4 (11) | C27—C28—C29—C30 | −3 (3) |
Cu1—O3—C8—C9 | 179.8 (5) | F10—C28—C29—C30 | 179.8 (16) |
O4—C8—C9—C14 | 166.9 (8) | C27—C28—C29—F11 | −177.1 (17) |
O3—C8—C9—C14 | −11.6 (12) | F10—C28—C29—F11 | 5 (3) |
O4—C8—C9—C10 | −12.7 (13) | C28—C29—C30—C31 | −1 (3) |
O3—C8—C9—C10 | 168.8 (8) | F11—C29—C30—C31 | 173.7 (17) |
C14—C9—C10—F5 | 179.3 (9) | C28—C29—C30—F12 | −176 (2) |
C8—C9—C10—F5 | −1.1 (15) | F11—C29—C30—F12 | −1 (3) |
C14—C9—C10—C11 | −0.4 (15) | F12—C30—C31—C32 | 179.6 (16) |
C8—C9—C10—C11 | 179.2 (9) | C29—C30—C31—C32 | 5 (3) |
F5—C10—C11—C12 | 177.8 (10) | C28—C27—C32—C31 | 1 (3) |
C9—C10—C11—C12 | −2.5 (17) | F9—C27—C32—C31 | 178.7 (17) |
F5—C10—C11—F6 | 2.1 (14) | C30—C31—C32—C27 | −5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.85 | 2.05 | 2.776 (8) | 143 |
O5—H5B···O4i | 0.85 | 2.08 | 2.831 (7) | 147 |
C25—H25···O2ii | 0.93 | 2.53 | 3.221 (10) | 131 |
C26—H26···O4ii | 0.93 | 2.44 | 3.329 (10) | 159 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C13H6F4O2)2(C12H8N2)(H2O)]·C6H2F4 |
Mr | 797.99 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 6.8150 (8), 28.9810 (16), 15.44800 (8) |
β (°) | 99.226 (2) |
V (Å3) | 3011.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.85 |
Crystal size (mm) | 0.37 × 0.15 × 0.14 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.745, 0.891 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14410, 5137, 2352 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.241, 1.03 |
No. of reflections | 5137 |
No. of parameters | 450 |
No. of restraints | 594 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.77, −0.68 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.85 | 2.05 | 2.776 (8) | 142.9 |
O5—H5B···O4i | 0.85 | 2.08 | 2.831 (7) | 147.2 |
C25—H25···O2ii | 0.93 | 2.53 | 3.221 (10) | 131.1 |
C26—H26···O4ii | 0.93 | 2.44 | 3.329 (10) | 158.8 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+2. |
Metal complexes with carboxylates are among the most investigated complexes in the field of coordination chemistry. Nevertheless, the crystal structures of metal complexes with fluorated carboxylic ligands have rarely been reported. In our work, we have reported the organotin(IV) carboxylates complexes with this ligand (Ma et al., 2006). In continuation of this study, we present here the crystal structure of the title compound.
In the title compound (Fig. 1), the CuII ion exhibits a five-coordinated square-pyramidal environment formed by three O atoms from two carboxylic ligands (Cu1—O1 1.922 (6) Å, Cu1—O3 1.948 (5) Å) and one water molecule (Cu1—O5 2.243 (5) Å), and two N atoms (Cu1—N1 1.985 (6) Å, Cu1—N2 2.052 (6) Å) from 1,10-phenanthroline ligand. Two N atoms and two O atoms form the basal plane and atom O5 occupies the apical site.
The intermolecular O—H···O hydrogen bonds (Table 1) link the main molecules related by translation along a axis into chains. The crystal packing exhibits also weak C—H···O hydrogen bonds (Table 1) and π···π interactions, proved by short distance of 3.717 (13) Å between the centroids of benzene rings of neighbouring solvent molecules.