The title compound, [Cu(C2H8N2)(H2O)2](C7H4FO2)2, is a mononuclear complex. The CuII atom, which lies on a crystallographic inversion centre, is coordinated by four N atoms from two ethylenediamine ligands and two O atoms from two water molecules, to form a slightly distorted octahedral geometry. All the N atoms of the ethylenediamine ligands, and all the O atoms in the water molecules and 4-fluorobenzoate anions, contribute to the formation of a hydrogen-bonded three-dimensional network.
Supporting information
CCDC reference: 248721
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.057
- wR factor = 0.181
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.69
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT320_ALERT_2_C Check Hybridisation of C1 in Main Residue . ?
PLAT320_ALERT_2_C Check Hybridisation of C2 in Main Residue . ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.837(10) ...... 3.00 su-Rat
O1W -H1WA 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.836(10) ...... 4.00 su-Rat
O1W -H1WB 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.837(10) ...... 3.00 su-Rat
O1W -H1# 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.836(10) ...... 4.00 su-Rat
O1W -H2# 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.94(4), Rep 1.936(15) ...... 2.67 su-Rat
H1# -O1 1.555 2.565
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 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.
Diaquabis(ethylenediamine-
κ2N,
N')copper(II)
bis(4-fluorobenzoate)
top
Crystal data top
[Cu(C2H8N2)(H2O)2](C7H4FO2)2 | Z = 1 |
Mr = 497.98 | F(000) = 259 |
Triclinic, P1 | Dx = 1.467 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.131 (1) Å | Cell parameters from 2238 reflections |
b = 7.144 (1) Å | θ = 6–28° |
c = 14.498 (3) Å | µ = 1.03 mm−1 |
α = 95.72 (3)° | T = 293 K |
β = 96.37 (3)° | Block, violet |
γ = 115.15 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 563.6 (2) Å3 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2238 independent reflections |
Radiation source: fine-focus sealed tube | 2167 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 26.5°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.748, Tmax = 0.904 | k = −8→8 |
4314 measured reflections | l = −18→18 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | w = 1/[σ2(Fo2) + (0.067P)2 + 1.8621P] where P = (Fo2 + 2Fc2)/3 |
2238 reflections | (Δ/σ)max < 0.001 |
148 parameters | Δρmax = 1.74 e Å−3 |
3 restraints | Δρmin = −0.37 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 | |
Cu1 | 0.0000 | 0.0000 | 0.0000 | 0.0313 (3) | |
C1 | 0.3277 (10) | 0.1528 (9) | 0.1766 (4) | 0.0480 (13) | |
H1A | 0.4777 | 0.2513 | 0.2162 | 0.080* | |
H1C | 0.3193 | 0.0148 | 0.1722 | 0.080* | |
C2 | −0.0738 (11) | −0.0672 (8) | −0.2007 (3) | 0.0468 (12) | |
H2A | −0.0324 | −0.0246 | −0.2596 | 0.080* | |
H2B | −0.0607 | −0.1952 | −0.1956 | 0.080* | |
C3 | 0.3355 (9) | 0.6643 (7) | 0.3047 (3) | 0.0388 (10) | |
C4 | 0.5846 (11) | 0.7300 (10) | 0.3323 (4) | 0.0545 (14) | |
H4A | 0.6867 | 0.7425 | 0.2854 | 0.080* | |
C5 | 0.6884 (13) | 0.7780 (12) | 0.4266 (4) | 0.0668 (18) | |
H5A | 0.8609 | 0.8261 | 0.4460 | 0.080* | |
C6 | 0.5382 (13) | 0.7564 (11) | 0.4922 (4) | 0.0615 (16) | |
C7 | 0.2912 (14) | 0.6899 (12) | 0.4680 (4) | 0.0672 (18) | |
H7A | 0.1900 | 0.6746 | 0.5154 | 0.080* | |
C8 | 0.1910 (11) | 0.6424 (10) | 0.3736 (4) | 0.0529 (13) | |
H8A | 0.0181 | 0.5942 | 0.3553 | 0.080* | |
C9 | 0.2234 (9) | 0.6164 (7) | 0.2015 (3) | 0.0377 (10) | |
N1 | 0.3167 (7) | 0.2095 (6) | 0.0813 (3) | 0.0385 (9) | |
H1B | 0.3257 | 0.3392 | 0.0848 | 0.080* | |
H1D | 0.4440 | 0.2088 | 0.0561 | 0.080* | |
N2 | 0.0956 (7) | 0.0987 (6) | −0.1218 (3) | 0.0377 (9) | |
H2C | 0.2506 | 0.1209 | −0.1240 | 0.080* | |
H2D | 0.0850 | 0.2195 | −0.1260 | 0.080* | |
O1 | 0.3668 (7) | 0.6489 (6) | 0.1424 (2) | 0.0478 (9) | |
O2 | −0.0034 (7) | 0.5495 (6) | 0.1822 (3) | 0.0480 (9) | |
O1W | −0.2058 (7) | 0.2464 (5) | 0.0217 (3) | 0.0440 (8) | |
F1 | 0.6380 (10) | 0.8041 (8) | 0.5845 (3) | 0.0981 (16) | |
H1WA | −0.246 (11) | 0.273 (8) | −0.0307 (17) | 0.050* | |
H1WB | −0.164 (11) | 0.350 (6) | 0.064 (2) | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0283 (4) | 0.0323 (4) | 0.0284 (4) | 0.0086 (3) | 0.0053 (3) | 0.0055 (3) |
C1 | 0.045 (3) | 0.046 (3) | 0.040 (3) | 0.012 (2) | −0.009 (2) | 0.005 (2) |
C2 | 0.060 (3) | 0.043 (3) | 0.029 (2) | 0.015 (2) | 0.006 (2) | 0.007 (2) |
C3 | 0.041 (3) | 0.037 (2) | 0.035 (2) | 0.016 (2) | −0.0009 (19) | 0.0037 (19) |
C4 | 0.046 (3) | 0.065 (4) | 0.043 (3) | 0.018 (3) | 0.000 (2) | 0.005 (3) |
C5 | 0.059 (4) | 0.080 (5) | 0.046 (3) | 0.022 (3) | −0.010 (3) | 0.003 (3) |
C6 | 0.074 (4) | 0.065 (4) | 0.034 (3) | 0.026 (3) | −0.010 (3) | −0.002 (3) |
C7 | 0.080 (5) | 0.081 (5) | 0.034 (3) | 0.031 (4) | 0.010 (3) | 0.006 (3) |
C8 | 0.049 (3) | 0.066 (4) | 0.039 (3) | 0.023 (3) | 0.004 (2) | 0.005 (2) |
C9 | 0.047 (3) | 0.031 (2) | 0.037 (2) | 0.019 (2) | 0.004 (2) | 0.0062 (18) |
N1 | 0.036 (2) | 0.036 (2) | 0.041 (2) | 0.0140 (17) | 0.0064 (16) | 0.0028 (17) |
N2 | 0.038 (2) | 0.040 (2) | 0.035 (2) | 0.0161 (17) | 0.0075 (16) | 0.0072 (16) |
O1 | 0.051 (2) | 0.054 (2) | 0.0360 (18) | 0.0218 (18) | 0.0045 (15) | 0.0068 (16) |
O2 | 0.042 (2) | 0.051 (2) | 0.044 (2) | 0.0180 (17) | −0.0051 (15) | 0.0040 (16) |
O1W | 0.046 (2) | 0.0400 (18) | 0.044 (2) | 0.0185 (16) | 0.0045 (16) | 0.0037 (15) |
F1 | 0.118 (4) | 0.117 (4) | 0.0354 (19) | 0.040 (3) | −0.019 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
Cu1—N1i | 2.018 (4) | C4—H4A | 0.96 |
Cu1—N1 | 2.018 (4) | C5—C6 | 1.371 (10) |
Cu1—N2 | 2.021 (4) | C5—H5A | 0.96 |
Cu1—N2i | 2.021 (4) | C6—F1 | 1.354 (6) |
Cu1—O1W | 2.579 (4) | C6—C7 | 1.371 (10) |
C1—N1 | 1.481 (7) | C7—C8 | 1.382 (8) |
C1—C2i | 1.508 (8) | C7—H7A | 0.96 |
C1—H1A | 0.96 | C8—H8A | 0.96 |
C1—H1C | 0.96 | C9—O2 | 1.250 (6) |
C2—N2 | 1.487 (6) | C9—O1 | 1.263 (6) |
C2—C1i | 1.508 (8) | N1—H1B | 0.90 |
C2—H2A | 0.96 | N1—H1D | 0.90 |
C2—H2B | 0.96 | N2—H2C | 0.90 |
C3—C8 | 1.385 (8) | N2—H2D | 0.90 |
C3—C4 | 1.390 (8) | O1W—H1WA | 0.837 (10) |
C3—C9 | 1.515 (7) | O1W—H1WB | 0.836 (10) |
C4—C5 | 1.385 (8) | | |
| | | |
N1i—Cu1—N1 | 180.0 (3) | C6—C5—H5A | 120.4 |
N1i—Cu1—N2 | 84.95 (17) | C4—C5—H5A | 121.4 |
N1—Cu1—N2 | 95.05 (17) | F1—C6—C7 | 118.7 (6) |
N1i—Cu1—N2i | 95.05 (17) | F1—C6—C5 | 118.7 (6) |
N1—Cu1—N2i | 84.95 (17) | C7—C6—C5 | 122.6 (6) |
N2—Cu1—N2i | 180.0 (4) | C6—C7—C8 | 118.3 (6) |
N1i—Cu1—O1W | 87.24 (14) | C6—C7—H7A | 120.8 |
N1—Cu1—O1W | 92.76 (14) | C8—C7—H7A | 120.8 |
N2—Cu1—O1W | 91.01 (15) | C7—C8—C3 | 121.2 (6) |
N2i—Cu1—O1W | 88.99 (15) | C7—C8—H8A | 119.5 |
N1—C1—C2i | 108.5 (4) | C3—C8—H8A | 119.3 |
N1—C1—H1A | 110.1 | O2—C9—O1 | 125.5 (5) |
C2i—C1—H1A | 127.6 | O2—C9—C3 | 117.1 (4) |
N1—C1—H1C | 109.2 | O1—C9—C3 | 117.4 (4) |
C2i—C1—H1C | 89.4 | C1—N1—Cu1 | 109.2 (3) |
H1A—C1—H1C | 109.5 | C1—N1—H1B | 109.9 |
N2—C2—C1i | 108.3 (4) | Cu1—N1—H1B | 109.9 |
N2—C2—H2A | 109.8 | C1—N1—H1D | 109.6 |
C1i—C2—H2A | 125.0 | Cu1—N1—H1D | 109.8 |
N2—C2—H2B | 109.5 | H1B—N1—H1D | 108.4 |
C1i—C2—H2B | 93.1 | C2—N2—Cu1 | 107.9 (3) |
H2A—C2—H2B | 109.5 | C2—N2—H2C | 110.0 |
C8—C3—C4 | 118.5 (5) | Cu1—N2—H2C | 110.0 |
C8—C3—C9 | 120.5 (5) | C2—N2—H2D | 110.2 |
C4—C3—C9 | 121.0 (5) | Cu1—N2—H2D | 110.3 |
C5—C4—C3 | 121.1 (6) | H2C—N2—H2D | 108.5 |
C5—C4—H4A | 119.4 | Cu1—O1W—H1WA | 109 (4) |
C3—C4—H4A | 119.5 | Cu1—O1W—H1WB | 128 (4) |
C6—C5—C4 | 118.2 (6) | H1WA—O1W—H1WB | 111 (3) |
| | | |
C8—C3—C4—C5 | −1.6 (9) | C4—C3—C9—O2 | 177.0 (5) |
C9—C3—C4—C5 | 178.7 (6) | C8—C3—C9—O1 | 176.7 (5) |
C3—C4—C5—C6 | 0.8 (11) | C4—C3—C9—O1 | −3.6 (7) |
C4—C5—C6—F1 | −179.6 (6) | C2i—C1—N1—Cu1 | −36.2 (5) |
C4—C5—C6—C7 | −0.1 (11) | N2—Cu1—N1—C1 | −169.0 (3) |
F1—C6—C7—C8 | 179.7 (6) | N2i—Cu1—N1—C1 | 11.0 (3) |
C5—C6—C7—C8 | 0.3 (11) | O1W—Cu1—N1—C1 | 99.8 (3) |
C6—C7—C8—C3 | −1.1 (11) | C1i—C2—N2—Cu1 | 40.5 (5) |
C4—C3—C8—C7 | 1.7 (9) | N1i—Cu1—N2—C2 | −16.5 (3) |
C9—C3—C8—C7 | −178.5 (6) | N1—Cu1—N2—C2 | 163.5 (3) |
C8—C3—C9—O2 | −2.7 (7) | O1W—Cu1—N2—C2 | −103.6 (3) |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1 | 0.90 | 2.18 | 3.049 (6) | 161 |
N1—H1D···O1Wii | 0.90 | 2.17 | 3.057 (6) | 169 |
N2—H2C···O1iii | 0.90 | 2.29 | 3.079 (6) | 147 |
N2—H2D···O2iv | 0.90 | 2.13 | 2.990 (6) | 161 |
O1W—H1WA···O1iv | 0.84 (1) | 1.94 (2) | 2.766 (5) | 171 (6) |
O1W—H1WB···O2 | 0.84 (1) | 1.97 (2) | 2.778 (5) | 161 (5) |
Symmetry codes: (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z. |