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The title compound, (I), [Cu(trifacac)2(DabcoCH2Cl)](BF4)2 or [Cu(C5H4F3O2)2(C7H14ClN2)2](BF4)2 (Dabco is di­aza­bi­cyclo­[2.2.2]­octane and trifacac is tri­fluoro­acetyl­acetonate) was synthesized from the reaction of Selectfluor [Selectfluor is 1-(chloro­methyl)-4-fluoro-1,4-diazo­bi­cyclo­[2.2.2]­octane bis­(tetra­fluoro­borate)] and Cu(trifacac)2. The central Cu atom is octahedrally coordinated by two N(CH2CH2)3NCH2Cl+ and two trifacac ligands in a trans conformation. The Cu atom is located on a center of symmetry. The Cu—N and Cu—O distances are 2.5514 (19) and 1.9550 (15), 1.9592 (15) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018998/ac6017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018998/ac6017Isup2.hkl
Contains datablock I

CCDC reference: 200736

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.110
  • Data-to-parameter ratio = 17.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 1998); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.

(I) top
Crystal data top
[Cu(C5H4F3O2)2(C7H14ClN2)2](BF4)2F(000) = 878
Mr = 866.63Dx = 1.725 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.0098 (12) ÅCell parameters from 993 reflections
b = 15.1046 (18) Åθ = 2.3–28.2°
c = 11.5086 (14) ŵ = 0.93 mm1
β = 106.50 (2)°T = 203 K
V = 1668.4 (3) Å3Needle, pale green
Z = 20.60 × 0.25 × 0.13 mm
Data collection top
Bruker–Siemens SMART 1K
diffractometer
3984 independent reflections
Radiation source: normal-focus sealed tube3155 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.3 pixels mm-1θmax = 28.3°, θmin = 2.3°
ω scansh = 1313
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1999)
k = 1819
Tmin = 0.605, Tmax = 0.888l = 1015
12231 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.6096P]
where P = (Fo2 + 2Fc2)/3
3984 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
B10.2079 (3)0.1265 (2)0.0472 (3)0.0403 (7)
C10.7561 (2)0.05121 (14)0.56397 (19)0.0220 (4)
Cl10.56071 (7)0.15429 (5)0.11653 (6)0.03853 (17)
Cu11.00000.00000.50000.02212 (12)
F10.67556 (16)0.19566 (9)0.58291 (15)0.0404 (4)
N10.83990 (19)0.07461 (12)0.31309 (17)0.0255 (4)
O10.84246 (15)0.07439 (10)0.50653 (14)0.0237 (3)
C20.6326 (2)0.11524 (15)0.5415 (2)0.0274 (5)
F20.56977 (15)0.12368 (10)0.42243 (14)0.0407 (4)
N20.67670 (18)0.15257 (12)0.12796 (16)0.0232 (4)
O20.96487 (15)0.08689 (10)0.61427 (14)0.0250 (3)
C30.7607 (2)0.01914 (15)0.6394 (2)0.0271 (5)
H3A0.68830.02540.67590.032*
F30.53414 (15)0.09041 (11)0.59256 (16)0.0430 (4)
C40.8689 (2)0.08367 (14)0.6658 (2)0.0255 (5)
F40.2355 (2)0.15530 (16)0.0567 (2)0.0779 (7)
C50.8700 (3)0.15131 (19)0.7600 (3)0.0453 (7)
H5A0.96560.16620.80300.068*
H5B0.82360.12780.81670.068*
H5C0.82170.20400.72180.068*
F50.1693 (4)0.03928 (19)0.0313 (3)0.1206 (11)
C60.7802 (3)0.15455 (16)0.3506 (2)0.0312 (5)
H6A0.85470.19750.38370.037*
H6B0.73760.13930.41490.037*
F60.1053 (2)0.17137 (19)0.0748 (3)0.0925 (8)
C70.6697 (3)0.19699 (16)0.2443 (2)0.0324 (5)
H7A0.57680.18920.25520.039*
H7B0.68770.26060.24080.039*
F70.3282 (2)0.1318 (2)0.1411 (2)0.0929 (8)
C80.7245 (3)0.01555 (15)0.2512 (2)0.0341 (6)
H8A0.66620.00370.30500.041*
H8B0.76250.04100.23350.041*
C90.6344 (2)0.05671 (15)0.1325 (2)0.0299 (5)
H9A0.64820.02440.06300.036*
H9B0.53570.05300.12930.036*
C100.9156 (2)0.09994 (19)0.2260 (2)0.0351 (6)
H10A0.94650.04630.19310.042*
H10B0.99860.13390.26800.042*
C110.8251 (2)0.15566 (18)0.1210 (2)0.0331 (5)
H11A0.85850.21700.12770.040*
H11B0.83020.13170.04320.040*
C120.5778 (2)0.20234 (16)0.0269 (2)0.0291 (5)
H12A0.61080.26340.02660.035*
H12B0.48610.20430.04160.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0353 (15)0.0491 (18)0.0398 (17)0.0044 (13)0.0161 (13)0.0023 (14)
C10.0198 (9)0.0238 (10)0.0228 (11)0.0014 (8)0.0068 (8)0.0053 (8)
Cl10.0369 (3)0.0508 (4)0.0250 (3)0.0042 (3)0.0042 (2)0.0052 (3)
Cu10.02141 (19)0.02276 (19)0.0256 (2)0.00156 (14)0.01210 (15)0.00335 (15)
F10.0447 (8)0.0273 (7)0.0518 (10)0.0034 (6)0.0180 (7)0.0085 (7)
N10.0239 (9)0.0261 (10)0.0251 (10)0.0003 (7)0.0048 (7)0.0031 (8)
O10.0237 (7)0.0248 (8)0.0254 (8)0.0011 (6)0.0114 (6)0.0026 (6)
C20.0253 (11)0.0280 (11)0.0307 (12)0.0001 (9)0.0105 (9)0.0000 (9)
F20.0338 (8)0.0495 (9)0.0347 (8)0.0124 (7)0.0032 (6)0.0024 (7)
N20.0204 (8)0.0244 (9)0.0233 (9)0.0011 (7)0.0038 (7)0.0039 (7)
O20.0247 (7)0.0259 (8)0.0269 (8)0.0008 (6)0.0114 (6)0.0028 (6)
C30.0241 (11)0.0307 (12)0.0306 (12)0.0003 (8)0.0146 (9)0.0033 (9)
F30.0301 (7)0.0491 (9)0.0582 (10)0.0077 (6)0.0261 (7)0.0095 (8)
C40.0263 (11)0.0261 (11)0.0263 (11)0.0031 (8)0.0108 (9)0.0002 (9)
F40.0703 (14)0.1094 (18)0.0596 (13)0.0070 (12)0.0276 (11)0.0247 (12)
C50.0470 (15)0.0444 (16)0.0545 (18)0.0132 (12)0.0308 (14)0.0229 (13)
F50.182 (3)0.0709 (17)0.135 (3)0.0474 (19)0.086 (2)0.0223 (17)
C60.0318 (12)0.0331 (12)0.0257 (12)0.0034 (9)0.0032 (10)0.0030 (9)
F60.0580 (13)0.124 (2)0.105 (2)0.0286 (13)0.0383 (13)0.0027 (16)
C70.0386 (13)0.0297 (12)0.0269 (12)0.0074 (10)0.0059 (10)0.0019 (10)
F70.0428 (11)0.171 (3)0.0604 (14)0.0039 (13)0.0070 (10)0.0002 (15)
C80.0397 (14)0.0260 (12)0.0296 (13)0.0066 (9)0.0014 (11)0.0057 (9)
C90.0289 (11)0.0264 (11)0.0296 (12)0.0049 (9)0.0006 (9)0.0034 (9)
C100.0237 (11)0.0474 (15)0.0345 (14)0.0086 (10)0.0087 (10)0.0141 (11)
C110.0205 (11)0.0453 (14)0.0329 (13)0.0012 (9)0.0067 (9)0.0140 (11)
C120.0268 (11)0.0317 (12)0.0268 (12)0.0049 (9)0.0044 (9)0.0066 (9)
Geometric parameters (Å, º) top
B1—F61.342 (4)C3—C41.424 (3)
B1—F51.370 (4)C3—H3A0.9400
B1—F41.372 (4)C4—C51.488 (3)
B1—F71.373 (4)C5—H5A0.9700
C1—O11.278 (3)C5—H5B0.9700
C1—C31.364 (3)C5—H5C0.9700
C1—C21.533 (3)C6—C71.537 (3)
Cl1—C121.767 (2)C6—H6A0.9800
Cu1—O11.9550 (15)C6—H6B0.9800
Cu1—O1i1.9550 (15)C7—H7A0.9800
Cu1—O2i1.9591 (15)C7—H7B0.9800
Cu1—O21.9591 (15)C8—C91.538 (3)
F1—C21.331 (3)C8—H8A0.9800
N1—C61.466 (3)C8—H8B0.9800
N1—C101.469 (3)C9—H9A0.9800
N1—C81.473 (3)C9—H9B0.9800
C2—F31.336 (3)C10—C111.538 (3)
C2—F21.341 (3)C10—H10A0.9800
N2—C121.497 (3)C10—H10B0.9800
N2—C111.511 (3)C11—H11A0.9800
N2—C91.514 (3)C11—H11B0.9800
N2—C71.517 (3)C12—H12A0.9800
O2—C41.265 (3)C12—H12B0.9800
F6—B1—F5108.1 (3)H5B—C5—H5C109.5
F6—B1—F4113.8 (3)N1—C6—C7111.74 (19)
F5—B1—F4107.9 (3)N1—C6—H6A109.3
F6—B1—F7110.1 (3)C7—C6—H6A109.3
F5—B1—F7108.2 (3)N1—C6—H6B109.3
F4—B1—F7108.6 (3)C7—C6—H6B109.3
O1—C1—C3129.6 (2)H6A—C6—H6B107.9
O1—C1—C2111.83 (19)N2—C7—C6108.38 (18)
C3—C1—C2118.61 (19)N2—C7—H7A110.0
O1—Cu1—O1i180.0C6—C7—H7A110.0
O1—Cu1—O2i86.64 (6)N2—C7—H7B110.0
O1i—Cu1—O2i93.36 (6)C6—C7—H7B110.0
O1—Cu1—O293.36 (6)H7A—C7—H7B108.4
O1i—Cu1—O286.64 (6)N1—C8—C9111.45 (18)
O2i—Cu1—O2180.00 (7)N1—C8—H8A109.3
C6—N1—C10108.62 (19)C9—C8—H8A109.3
C6—N1—C8108.16 (18)N1—C8—H8B109.3
C10—N1—C8108.3 (2)C9—C8—H8B109.3
C1—O1—Cu1122.30 (14)H8A—C8—H8B108.0
F1—C2—F3107.59 (19)N2—C9—C8108.57 (18)
F1—C2—F2106.81 (19)N2—C9—H9A110.0
F3—C2—F2106.61 (19)C8—C9—H9A110.0
F1—C2—C1110.62 (18)N2—C9—H9B110.0
F3—C2—C1114.12 (19)C8—C9—H9B110.0
F2—C2—C1110.73 (18)H9A—C9—H9B108.4
C12—N2—C11112.72 (17)N1—C10—C11112.09 (19)
C12—N2—C9112.18 (17)N1—C10—H10A109.2
C11—N2—C9108.67 (18)C11—C10—H10A109.2
C12—N2—C7106.11 (17)N1—C10—H10B109.2
C11—N2—C7109.01 (18)C11—C10—H10B109.2
C9—N2—C7107.99 (18)H10A—C10—H10B107.9
C4—O2—Cu1126.42 (14)N2—C11—C10108.04 (18)
C1—C3—C4123.7 (2)N2—C11—H11A110.1
C1—C3—H3A118.1C10—C11—H11A110.1
C4—C3—H3A118.1N2—C11—H11B110.1
O2—C4—C3124.0 (2)C10—C11—H11B110.1
O2—C4—C5117.7 (2)H11A—C11—H11B108.4
C3—C4—C5118.3 (2)N2—C12—Cl1112.75 (16)
C4—C5—H5A109.5N2—C12—H12A109.0
C4—C5—H5B109.5Cl1—C12—H12A109.0
H5A—C5—H5B109.5N2—C12—H12B109.0
C4—C5—H5C109.5Cl1—C12—H12B109.0
H5A—C5—H5C109.5H12A—C12—H12B107.8
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···F40.982.553.362 (3)140
C9—H9B···F70.982.433.296 (3)147
C12—H12B···F70.982.463.312 (3)146
C12—H12A···O1ii0.982.543.512 (3)170
Symmetry code: (ii) x+3/2, y+1/2, z+1/2.
A comparison of the Cu—N distances and angles between compound (I) and reported values in the CSD (Å, °). top
RefcodeCu—NN—Cu—N
(I)2.5514 (19)180.00
HOYZIE2.389 (5)180.00
KOWFIL2.545 (4)180.00
LECWEV2.537 (10)180.00
QOTMUH2.445 (2)180.00
 

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