Buy article online - an online subscription or single-article purchase is required to access this article.
The asymmetric unit of the title compound bis[
N-(2-hydroxyethyl)ethylenediamine-κ
3N,N′,O]copper(II) bis(4-fluorobenzoate), [Cu(C
4H
12N
2O)
2](C
7H
4FO
2)
2, contains one-half of a [Cu(C
4H
12N
2O)
2]
2+ complex cation (the other half is inversion-related) and a 4-fluorobenzoate anion. The Cu
II atom has a distorted octahedral coordination geometry and is surrounded by four N atoms and two O atoms from the two inversion-related
N-(2-hydroxyethyl)ethylenediamine ligands. In the crystal structure, the molecules are held together by intermolecular O—H
O and N—H
O hydrogen bonds, leading to the formation of a three-dimensional network.
Supporting information
CCDC reference: 248758
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.057
- wR factor = 0.168
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 1971
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2094
Completeness (_total/calc) 94.13%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21
PLAT320_ALERT_2_C Check Hybridisation of C10 in Main Residue . ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 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
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT; 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.
bis[
N-(2-hydroxyethyl)ethylenediamine-
κ3N,
N',
O]copper(II) bis(4-fluorobenzoate)
top
Crystal data top
[Cu(C4H12N2O)2](C7H4FO2)2 | Z = 1 |
Mr = 550.06 | F(000) = 287 |
Triclinic, P1 | Dx = 1.538 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.094 (2) Å | Cell parameters from 1012 reflections |
b = 7.353 (2) Å | θ = 2.5–19.7° |
c = 12.139 (2) Å | µ = 0.98 mm−1 |
α = 102.68 (3)° | T = 293 K |
β = 100.27 (3)° | Block, blue |
γ = 99.53 (3)° | 0.32 × 0.22 × 0.18 mm |
V = 593.9 (2) Å3 | |
Data collection top
SMART CCD area-detector diffractometer | 1971 independent reflections |
Radiation source: fine-focus sealed tube | 1470 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.744, Tmax = 0.843 | k = −7→8 |
3094 measured reflections | l = −14→12 |
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) = 0.168 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0946P)2] where P = (Fo2 + 2Fc2)/3 |
1971 reflections | (Δ/σ)max = 0.002 |
163 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −0.59 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 | 0.0253 (4) | |
O2 | 0.5196 (5) | 0.0973 (6) | 0.8471 (4) | 0.0440 (11) | |
O3 | 0.2861 (6) | 0.2258 (8) | 0.7681 (4) | 0.0555 (13) | |
N1 | 0.1979 (6) | 0.1662 (6) | 0.1453 (4) | 0.0281 (11) | |
H1A | 0.2661 | 0.0885 | 0.1749 | 0.080* | |
F1 | 0.8577 (6) | 0.2901 (8) | 0.4316 (4) | 0.0913 (16) | |
C1 | 0.5641 (9) | 0.2670 (10) | 0.4943 (6) | 0.0508 (18) | |
H1 | 0.5006 | 0.2922 | 0.4242 | 0.080* | |
C2 | 0.7588 (10) | 0.2610 (11) | 0.5142 (6) | 0.0541 (19) | |
C3 | 0.8561 (8) | 0.2319 (11) | 0.6139 (6) | 0.0520 (18) | |
H3 | 0.9935 | 0.2314 | 0.6260 | 0.080* | |
C4 | 0.7537 (8) | 0.2016 (9) | 0.6966 (5) | 0.0377 (15) | |
H4 | 0.8195 | 0.1765 | 0.7662 | 0.080* | |
C5 | 0.5553 (7) | 0.2056 (8) | 0.6807 (5) | 0.0336 (14) | |
C6 | 0.4625 (8) | 0.2396 (10) | 0.5791 (5) | 0.0453 (17) | |
H6 | 0.3258 | 0.2430 | 0.5672 | 0.080* | |
C7 | 0.4445 (7) | 0.1730 (8) | 0.7719 (5) | 0.0345 (14) | |
C8 | 0.2419 (8) | 0.4153 (8) | 0.0358 (6) | 0.0387 (15) | |
H8A | 0.3398 | 0.4923 | 0.0104 | 0.080* | |
H8B | 0.1728 | 0.4985 | 0.0775 | 0.080* | |
C9 | 0.3400 (7) | 0.3095 (9) | 0.1159 (5) | 0.0384 (15) | |
H9A | 0.4288 | 0.2460 | 0.0790 | 0.080* | |
H9B | 0.4154 | 0.3999 | 0.1858 | 0.080* | |
C10 | 0.0875 (8) | 0.2407 (9) | 0.2299 (5) | 0.0391 (15) | |
H10A | 0.1778 | 0.3196 | 0.2989 | 0.080* | |
H10C | 0.0114 | 0.1351 | 0.2480 | 0.080* | |
O1 | 0.1077 (5) | 0.2872 (6) | −0.0617 (4) | 0.0372 (10) | |
C11 | −0.1002 (7) | 0.2859 (9) | 0.1697 (5) | 0.0362 (15) | |
H11A | −0.1858 | 0.3067 | 0.2231 | 0.043* | |
H11B | −0.0694 | 0.4008 | 0.1438 | 0.043* | |
N2 | −0.1986 (6) | 0.1225 (6) | 0.0694 (4) | 0.0294 (11) | |
H2A | −0.2732 | 0.1632 | 0.0156 | 0.035* | |
H2B | −0.2776 | 0.0361 | 0.0923 | 0.035* | |
H1B | 0.157 (11) | 0.254 (12) | −0.115 (7) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0173 (5) | 0.0271 (6) | 0.0332 (6) | 0.0046 (4) | 0.0084 (4) | 0.0092 (5) |
O2 | 0.036 (2) | 0.061 (3) | 0.046 (3) | 0.012 (2) | 0.013 (2) | 0.034 (2) |
O3 | 0.041 (2) | 0.090 (4) | 0.055 (3) | 0.034 (2) | 0.021 (2) | 0.035 (3) |
N1 | 0.027 (2) | 0.030 (3) | 0.034 (3) | 0.0109 (19) | 0.012 (2) | 0.013 (2) |
F1 | 0.090 (3) | 0.139 (5) | 0.065 (3) | 0.019 (3) | 0.050 (3) | 0.046 (3) |
C1 | 0.058 (4) | 0.069 (5) | 0.034 (4) | 0.019 (4) | 0.011 (3) | 0.025 (4) |
C2 | 0.057 (4) | 0.070 (5) | 0.044 (4) | 0.010 (4) | 0.025 (4) | 0.025 (4) |
C3 | 0.031 (3) | 0.074 (5) | 0.059 (5) | 0.010 (3) | 0.014 (3) | 0.029 (4) |
C4 | 0.032 (3) | 0.045 (4) | 0.039 (4) | 0.006 (3) | 0.008 (3) | 0.019 (3) |
C5 | 0.030 (3) | 0.042 (4) | 0.036 (3) | 0.008 (3) | 0.007 (3) | 0.023 (3) |
C6 | 0.036 (3) | 0.063 (5) | 0.042 (4) | 0.013 (3) | 0.007 (3) | 0.025 (3) |
C7 | 0.024 (3) | 0.041 (4) | 0.041 (4) | 0.006 (3) | 0.007 (3) | 0.015 (3) |
C8 | 0.030 (3) | 0.032 (3) | 0.059 (4) | 0.004 (3) | 0.015 (3) | 0.018 (3) |
C9 | 0.022 (3) | 0.049 (4) | 0.046 (4) | 0.003 (3) | 0.007 (3) | 0.019 (3) |
C10 | 0.033 (3) | 0.056 (4) | 0.033 (3) | 0.012 (3) | 0.011 (3) | 0.017 (3) |
O1 | 0.032 (2) | 0.044 (3) | 0.041 (3) | 0.0069 (18) | 0.0129 (19) | 0.019 (2) |
C11 | 0.025 (3) | 0.046 (4) | 0.047 (4) | 0.014 (3) | 0.018 (3) | 0.018 (3) |
N2 | 0.024 (2) | 0.037 (3) | 0.030 (3) | 0.005 (2) | 0.009 (2) | 0.013 (2) |
Geometric parameters (Å, º) top
Cu1—N2i | 2.004 (4) | C4—H4 | 0.96 |
Cu1—N2 | 2.004 (4) | C5—C6 | 1.384 (8) |
Cu1—N1i | 2.044 (4) | C5—C7 | 1.505 (8) |
Cu1—N1 | 2.044 (4) | C6—H6 | 0.96 |
Cu1—O1i | 2.443 (4) | C8—O1 | 1.416 (7) |
Cu1—O1 | 2.443 (4) | C8—C9 | 1.518 (8) |
O2—C7 | 1.254 (7) | C8—H8A | 0.96 |
O3—C7 | 1.245 (6) | C8—H8B | 0.96 |
N1—C10 | 1.466 (7) | C9—H9A | 0.96 |
N1—C9 | 1.482 (6) | C9—H9B | 0.96 |
N1—H1A | 0.90 | C10—C11 | 1.524 (7) |
F1—C2 | 1.357 (7) | C10—H10A | 0.96 |
C1—C2 | 1.369 (9) | C10—H10C | 0.96 |
C1—C6 | 1.388 (9) | O1—H1B | 0.81 (8) |
C1—H1 | 0.96 | C11—N2 | 1.480 (7) |
C2—C3 | 1.361 (9) | C11—H11A | 0.97 |
C3—C4 | 1.374 (8) | C11—H11B | 0.97 |
C3—H3 | 0.96 | N2—H2A | 0.90 |
C4—C5 | 1.392 (7) | N2—H2B | 0.90 |
| | | |
N2i—Cu1—N2 | 180.0 (2) | C5—C6—H6 | 119.2 |
N2i—Cu1—N1i | 85.22 (17) | C1—C6—H6 | 119.9 |
N2—Cu1—N1i | 94.78 (17) | O3—C7—O2 | 124.8 (5) |
N2i—Cu1—N1 | 94.78 (17) | O3—C7—C5 | 117.4 (5) |
N2—Cu1—N1 | 85.22 (17) | O2—C7—C5 | 117.8 (5) |
N1i—Cu1—N1 | 180.0 (2) | O1—C8—C9 | 111.4 (5) |
N2i—Cu1—O1i | 89.68 (15) | O1—C8—H8A | 109.5 |
N2—Cu1—O1i | 90.32 (15) | C9—C8—H8A | 109.5 |
N1—Cu1—O1i | 101.78 (15) | O1—C8—H8B | 109.0 |
N1i—Cu1—O1i | 78.22 (15) | C9—C8—H8B | 109.3 |
N2i—Cu1—O1 | 90.32 (15) | H8A—C8—H8B | 108.1 |
N2—Cu1—O1 | 89.68 (15) | N1—C9—C8 | 112.8 (4) |
N1—Cu1—O1 | 78.22 (15) | N1—C9—H9A | 108.8 |
N1i—Cu1—O1 | 101.78 (15) | C8—C9—H9A | 108.9 |
O1i—Cu1—O1 | 180.00 (16) | N1—C9—H9B | 109.2 |
C10—N1—C9 | 116.3 (5) | C8—C9—H9B | 109.2 |
C10—N1—Cu1 | 107.8 (3) | H9A—C9—H9B | 107.8 |
C9—N1—Cu1 | 111.0 (3) | N1—C10—C11 | 110.8 (5) |
C10—N1—H1A | 107.4 | N1—C10—H10A | 109.2 |
C9—N1—H1A | 107.1 | C11—C10—H10A | 126.2 |
Cu1—N1—H1A | 106.9 | N1—C10—H10C | 108.6 |
C2—C1—C6 | 118.2 (6) | C11—C10—H10C | 90.0 |
C2—C1—H1 | 120.7 | H10A—C10—H10C | 109.5 |
C6—C1—H1 | 121.1 | C8—O1—H1B | 113 (6) |
F1—C2—C3 | 119.4 (6) | N2—C11—C10 | 108.4 (5) |
F1—C2—C1 | 117.9 (6) | N2—C11—H11A | 110.0 |
C3—C2—C1 | 122.7 (6) | C10—C11—H11A | 110.0 |
C2—C3—C4 | 118.8 (6) | N2—C11—H11B | 110.0 |
C2—C3—H3 | 120.6 | C10—C11—H11B | 110.0 |
C4—C3—H3 | 120.6 | H11A—C11—H11B | 108.4 |
C3—C4—C5 | 121.0 (5) | C11—N2—Cu1 | 110.5 (3) |
C3—C4—H4 | 119.6 | C11—N2—H2A | 109.6 |
C5—C4—H4 | 119.4 | Cu1—N2—H2A | 109.6 |
C6—C5—C4 | 118.5 (5) | C11—N2—H2B | 109.6 |
C6—C5—C7 | 120.9 (5) | Cu1—N2—H2B | 109.6 |
C4—C5—C7 | 120.6 (5) | H2A—N2—H2B | 108.1 |
C5—C6—C1 | 120.9 (6) | | |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O3ii | 0.81 (8) | 1.81 (8) | 2.606 (6) | 170 (9) |
N2—H2B···O2iii | 0.90 | 2.16 | 3.025 (5) | 161 |
N2—H2A···O2iv | 0.90 | 2.20 | 3.008 (6) | 149 |
N1—H1A···O2v | 0.90 | 2.22 | 3.013 (6) | 147 |
Symmetry codes: (ii) x, y, z−1; (iii) −x, −y, −z+1; (iv) x−1, y, z−1; (v) −x+1, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.