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The crystal structures of mono- and dinuclear CuII tri­fluoro­methane­sulfonate (triflate) complexes with benzyl­dipicolyl­amine (BDPA) are described. From equimolar amounts of Cu(triflate)2 and BDPA, a water-bound CuII mononuclear complex, aqua(benzyldipicolylamine-κ3N,N′,N′′)bis(trifluoromethanesulfonato-κO)copper(II) tetrahydrofuran monosolvate, [Cu(CF3SO3)2(C19H19N3)(H2O)]·C4H8O, (I), and a triflate-bridged CuII dinuclear complex, bis(μ-trifluoro­me­thanesulfonato-κ2O:O′)bis[(benzyldipicolylamine-κ3N,N′,N′′)(trifluoromethane­sulfonato-κO)copper(II)], [Cu2(CF3SO3)4(C19H19N3)2], were synthesized. The presence of residual moisture in the reaction medium afforded water-bound complex (I), whereas dinuclear complex (II) was synthesized from an anhydrous reaction medium. Single-crystal X-ray structure analysis reveals that the CuII centres adopt slightly distorted octa­hedral geometries in both complexes. The metal-bound water mol­ecule in (I) is involved in inter­molecular O—H...O hydrogen bonds with triflate ligands and tetrahydrofuran solvent molecules. In (II), weak inter­molecular C—H...F(triflate) and C—H...O(triflate) hydrogen bonds stabilize the crystal lattice. Complexes (I) and (II) were also characterized fully using FT–IR and UV–Vis spectroscopy, cyclic voltammetry and elemental analysis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617012785/fp3041sup1.cif
Contains datablocks I, II, global

CCDC references: 1561680; 1561883

Computing details top

For both structures, data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXS-97 (Sheldrick, 2008) for (II). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for (I); SHELXL-97 (Sheldrick, 2008) for (II). For both structures, molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Aqua(benzyldipicolylamine-κ3N,N',N'')bis(trifluoromethanesulfonato-κO)copper(II) tetrahydrofuran monosolvate (I) top
Crystal data top
[Cu(CF3O3S)2(C19H19N3)(H2O)]·C4H8OZ = 2
Mr = 741.17F(000) = 758
Triclinic, P1Dx = 1.613 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8133 (19) ÅCell parameters from 1904 reflections
b = 11.800 (3) Åθ = 2.6–21.9°
c = 15.404 (3) ŵ = 0.94 mm1
α = 96.363 (5)°T = 200 K
β = 93.886 (5)°Block, blue
γ = 105.518 (5)°0.23 × 0.11 × 0.11 mm
V = 1526.1 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
5373 independent reflections
Radiation source: fine-focus sealed tube2353 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.802, Tmax = 0.903k = 1214
8947 measured reflectionsl = 1618
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 0.73 w = 1/[σ2(Fo2) + (0.0173P)2]
where P = (Fo2 + 2Fc2)/3
5373 reflections(Δ/σ)max < 0.001
411 parametersΔρmax = 0.48 e Å3
2 restraintsΔρmin = 0.37 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C250.0731 (11)0.4114 (10)0.6205 (7)0.145 (4)
H25A0.16010.37020.57440.175*
H25B0.08390.49100.64140.175*
Cu10.74646 (8)0.97585 (6)0.72992 (4)0.0382 (2)
O10.7993 (5)1.1045 (4)0.6564 (3)0.0504 (12)
H10.71571.11230.63150.076*
N10.9217 (5)0.9089 (4)0.6989 (3)0.0375 (12)
C11.0085 (7)0.9304 (5)0.6300 (4)0.0488 (17)
H1A0.98860.98470.59260.059*
C21.1248 (7)0.8751 (6)0.6130 (4)0.0551 (18)
H21.18710.89340.56580.066*
C31.1493 (7)0.7943 (6)0.6645 (4)0.0613 (19)
H31.22640.75330.65220.074*
C41.0608 (7)0.7716 (5)0.7356 (4)0.0494 (17)
H41.07730.71590.77280.059*
C50.9494 (6)0.8317 (5)0.7505 (3)0.0358 (14)
C60.8532 (6)0.8209 (5)0.8288 (3)0.0371 (15)
H6A0.83670.74060.84630.044*
H6B0.91140.87960.87910.044*
N20.7002 (5)0.8418 (4)0.8061 (3)0.0342 (12)
C70.5855 (6)0.7349 (4)0.7534 (3)0.0377 (15)
H7A0.63200.71520.69900.045*
H7B0.48790.75670.73590.045*
C80.5391 (7)0.6247 (5)0.7976 (3)0.0385 (15)
C90.6154 (7)0.5390 (5)0.7835 (4)0.0503 (17)
H90.69850.55080.74640.060*
C100.5752 (8)0.4336 (6)0.8220 (4)0.067 (2)
H100.62750.37380.81000.081*
C110.4564 (9)0.4199 (6)0.8780 (4)0.067 (2)
H110.42930.35130.90700.081*
C120.3796 (8)0.5038 (6)0.8913 (4)0.068 (2)
H120.29660.49280.92850.082*
C130.4192 (7)0.6052 (5)0.8518 (4)0.0542 (18)
H130.36290.66300.86200.065*
N30.5624 (5)1.0108 (4)0.7802 (3)0.0353 (12)
C140.4726 (7)1.0774 (5)0.7520 (4)0.0477 (17)
H140.49991.11570.70190.057*
C150.3421 (7)1.0934 (5)0.7919 (4)0.0529 (17)
H150.28251.14230.77020.064*
C160.3016 (7)1.0367 (6)0.8632 (4)0.0559 (18)
H160.21331.04630.89230.067*
C170.3892 (6)0.9664 (5)0.8922 (4)0.0447 (16)
H170.35930.92460.94040.054*
C180.5204 (6)0.9555 (5)0.8521 (3)0.0356 (14)
C190.6315 (6)0.8884 (5)0.8817 (3)0.0358 (14)
H19A0.71710.94150.92430.043*
H19B0.57400.82200.91140.043*
S10.54892 (19)0.83768 (13)0.50701 (10)0.0446 (4)
O20.5680 (4)0.8758 (3)0.5990 (2)0.0501 (11)
O30.4030 (5)0.8420 (3)0.4633 (2)0.0593 (12)
O40.6865 (5)0.8798 (4)0.4615 (3)0.0796 (15)
C200.5276 (9)0.6802 (6)0.5003 (4)0.0585 (19)
F10.4985 (5)0.6269 (3)0.4182 (2)0.0921 (14)
F20.4067 (5)0.6287 (3)0.5444 (2)0.0841 (13)
F30.6566 (5)0.6577 (3)0.5359 (2)0.0817 (12)
S20.97200 (18)0.17906 (14)0.93689 (10)0.0423 (4)
O50.9239 (4)0.1301 (3)0.8473 (2)0.0624 (13)
O61.1367 (4)0.2387 (3)0.9567 (2)0.0581 (12)
O70.9050 (4)0.1005 (3)0.9978 (2)0.0504 (11)
C210.8772 (8)0.2939 (6)0.9548 (5)0.064 (2)
F40.9208 (5)0.3800 (3)0.9082 (3)0.1041 (16)
F50.7203 (4)0.2514 (3)0.9410 (3)0.0886 (13)
F60.9056 (5)0.3439 (4)1.0397 (3)0.0978 (14)
O80.0659 (10)0.3398 (7)0.6943 (4)0.182 (4)
C240.0696 (14)0.4174 (11)0.5927 (7)0.170 (5)
H24A0.12500.50000.58510.204*
H24B0.05860.36620.53580.204*
C220.0792 (15)0.3717 (12)0.7265 (7)0.186 (6)
H22A0.10560.44990.76350.223*
H22B0.10330.31250.76200.223*
C230.1538 (14)0.3773 (15)0.6581 (7)0.263 (10)
H23A0.16460.29790.63650.315*
H23B0.26120.43260.67270.315*
H1B0.849 (6)1.176 (2)0.669 (3)0.05 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C250.093 (8)0.251 (14)0.125 (9)0.084 (8)0.010 (7)0.069 (9)
Cu10.0419 (4)0.0443 (5)0.0287 (4)0.0082 (3)0.0091 (3)0.0118 (3)
O10.054 (3)0.047 (3)0.046 (3)0.000 (3)0.001 (2)0.022 (2)
N10.037 (3)0.046 (3)0.025 (3)0.001 (2)0.008 (2)0.006 (2)
C10.049 (4)0.059 (5)0.038 (4)0.011 (3)0.012 (3)0.012 (3)
C20.048 (4)0.067 (5)0.051 (4)0.014 (4)0.023 (4)0.006 (4)
C30.046 (4)0.077 (6)0.062 (5)0.024 (4)0.013 (4)0.007 (4)
C40.043 (4)0.057 (5)0.049 (4)0.014 (3)0.003 (3)0.011 (3)
C50.026 (3)0.045 (4)0.031 (3)0.003 (3)0.001 (3)0.005 (3)
C60.031 (3)0.043 (4)0.035 (4)0.007 (3)0.005 (3)0.009 (3)
N20.040 (3)0.039 (3)0.021 (3)0.006 (2)0.004 (2)0.003 (2)
C70.040 (3)0.038 (4)0.034 (3)0.007 (3)0.003 (3)0.006 (3)
C80.040 (4)0.038 (4)0.033 (3)0.005 (3)0.001 (3)0.001 (3)
C90.051 (4)0.048 (5)0.050 (4)0.010 (3)0.012 (3)0.007 (3)
C100.089 (5)0.046 (5)0.070 (5)0.022 (4)0.004 (4)0.018 (4)
C110.092 (6)0.044 (5)0.063 (5)0.007 (4)0.004 (4)0.026 (4)
C120.082 (5)0.055 (5)0.062 (5)0.001 (4)0.033 (4)0.011 (4)
C130.059 (4)0.044 (4)0.060 (4)0.011 (3)0.024 (4)0.008 (3)
N30.048 (3)0.030 (3)0.027 (3)0.008 (2)0.001 (2)0.007 (2)
C140.052 (4)0.046 (4)0.042 (4)0.008 (3)0.002 (3)0.006 (3)
C150.047 (4)0.046 (4)0.070 (5)0.023 (3)0.006 (4)0.001 (4)
C160.047 (4)0.064 (5)0.058 (5)0.015 (4)0.020 (4)0.002 (4)
C170.038 (4)0.056 (5)0.039 (4)0.010 (3)0.018 (3)0.002 (3)
C180.039 (4)0.031 (4)0.029 (3)0.000 (3)0.001 (3)0.002 (3)
C190.043 (4)0.043 (4)0.023 (3)0.011 (3)0.009 (3)0.006 (3)
S10.0575 (11)0.0448 (11)0.0328 (9)0.0145 (8)0.0041 (8)0.0094 (8)
O20.078 (3)0.047 (3)0.028 (2)0.021 (2)0.001 (2)0.0071 (19)
O30.070 (3)0.063 (3)0.046 (3)0.022 (2)0.010 (2)0.013 (2)
O40.078 (3)0.090 (4)0.071 (3)0.008 (3)0.041 (3)0.034 (3)
C200.080 (5)0.063 (5)0.035 (4)0.023 (4)0.012 (4)0.007 (4)
F10.152 (4)0.073 (3)0.051 (3)0.041 (3)0.008 (3)0.017 (2)
F20.102 (3)0.057 (3)0.082 (3)0.003 (2)0.017 (3)0.016 (2)
F30.107 (3)0.082 (3)0.077 (3)0.059 (3)0.008 (2)0.017 (2)
S20.0443 (10)0.0431 (10)0.0366 (10)0.0078 (8)0.0055 (8)0.0037 (8)
O50.068 (3)0.073 (3)0.028 (2)0.009 (2)0.001 (2)0.003 (2)
O60.037 (2)0.067 (3)0.059 (3)0.003 (2)0.007 (2)0.000 (2)
O70.054 (3)0.045 (3)0.047 (3)0.001 (2)0.003 (2)0.015 (2)
C210.049 (5)0.066 (6)0.078 (6)0.014 (4)0.008 (4)0.023 (5)
F40.125 (4)0.064 (3)0.133 (4)0.025 (3)0.023 (3)0.054 (3)
F50.061 (3)0.087 (3)0.129 (4)0.035 (2)0.008 (3)0.028 (3)
F60.125 (4)0.079 (3)0.093 (4)0.041 (3)0.024 (3)0.012 (3)
O80.175 (7)0.204 (8)0.077 (5)0.101 (6)0.032 (5)0.050 (5)
C240.148 (10)0.291 (15)0.115 (9)0.086 (10)0.044 (8)0.128 (10)
C220.152 (11)0.251 (15)0.112 (10)0.017 (11)0.053 (9)0.071 (10)
C230.211 (14)0.61 (3)0.094 (9)0.266 (17)0.114 (9)0.166 (14)
Geometric parameters (Å, º) top
Cu1—O11.969 (3)N3—C181.369 (6)
Cu1—N11.977 (5)C14—C151.387 (7)
Cu1—N22.043 (4)C15—C161.367 (7)
Cu1—N31.964 (5)C16—C171.365 (7)
C25—C241.342 (10)C17—C181.376 (7)
C25—O81.498 (9)C18—C191.493 (7)
N1—C51.332 (6)S1—O21.423 (4)
N1—C11.357 (6)S1—O31.427 (4)
C1—C21.379 (8)S1—O41.442 (4)
C2—C31.356 (8)S1—C201.807 (7)
C3—C41.396 (7)C20—F11.325 (7)
C4—C51.374 (7)C20—F31.331 (7)
C5—C61.518 (7)C20—F21.345 (6)
C6—N21.461 (6)S2—O51.426 (4)
N2—C191.468 (6)S2—O61.428 (4)
N2—C71.501 (6)S2—O71.436 (3)
C7—C81.507 (6)S2—C211.780 (7)
C8—C91.363 (8)C21—F41.298 (6)
C8—C131.377 (7)C21—F51.332 (6)
C9—C101.407 (7)C21—F61.352 (7)
C10—C111.390 (8)O8—C221.279 (10)
C11—C121.346 (9)C24—C231.408 (12)
C12—C131.375 (7)C22—C231.278 (12)
N3—C141.339 (7)
N3—Cu1—O199.34 (19)N3—C14—C15123.6 (5)
N3—Cu1—N1165.45 (17)C16—C15—C14118.2 (6)
O1—Cu1—N195.19 (18)C17—C16—C15119.4 (6)
N3—Cu1—N282.69 (17)C16—C17—C18120.5 (5)
O1—Cu1—N2177.83 (19)N3—C18—C17121.0 (5)
N1—Cu1—N282.77 (17)N3—C18—C19113.6 (5)
C5—N1—Cu1114.5 (4)C17—C18—C19125.3 (5)
C1—N1—Cu1126.7 (4)N2—C19—C18110.1 (4)
C24—C25—O899.4 (8)O2—S1—O3114.4 (3)
C5—N1—C1118.8 (5)O2—S1—O4115.6 (3)
N1—C1—C2121.5 (6)O3—S1—O4115.1 (2)
C3—C2—C1119.3 (6)O2—S1—C20103.3 (3)
C2—C3—C4119.7 (6)O3—S1—C20102.9 (3)
C5—C4—C3118.4 (6)O4—S1—C20103.1 (3)
N1—C5—C4122.3 (5)F1—C20—F3107.8 (6)
N1—C5—C6114.2 (5)F1—C20—F2107.7 (6)
C4—C5—C6123.5 (5)F3—C20—F2107.0 (5)
N2—C6—C5109.9 (4)F1—C20—S1112.2 (4)
C6—N2—C19113.8 (4)F3—C20—S1112.0 (5)
C6—N2—C7112.0 (4)F2—C20—S1110.0 (5)
C19—N2—C7111.9 (4)O5—S2—O6115.2 (2)
C6—N2—Cu1105.3 (3)O5—S2—O7113.5 (2)
C19—N2—Cu1104.7 (3)O6—S2—O7115.2 (2)
C7—N2—Cu1108.4 (3)O5—S2—C21104.4 (3)
N2—C7—C8116.7 (4)O6—S2—C21104.1 (3)
C9—C8—C13117.7 (5)O7—S2—C21102.3 (3)
C9—C8—C7119.9 (5)F4—C21—F5108.2 (6)
C13—C8—C7122.5 (6)F4—C21—F6106.4 (6)
C8—C9—C10122.2 (6)F5—C21—F6104.6 (6)
C11—C10—C9117.8 (6)F4—C21—S2115.0 (5)
C12—C11—C10120.0 (6)F5—C21—S2111.5 (5)
C11—C12—C13121.0 (6)F6—C21—S2110.6 (5)
C12—C13—C8121.2 (6)C22—O8—C25105.3 (7)
C14—N3—C18117.2 (5)C25—C24—C23105.9 (8)
C14—N3—Cu1128.7 (4)C23—C22—O8102.9 (10)
C18—N3—Cu1114.0 (4)C22—C23—C24109.1 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.841.942.719 (5)153
O1—H1B···O8ii0.84 (2)1.86 (2)2.691 (8)172 (6)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z.
Bis(µ-trifluoromethanesulfonato-κ2O:O')bis[(benzyldipicolylamine-κ3N,N',N'')(trifluoromethanesulfonato-κO)copper(II)] (II) top
Crystal data top
[Cu2(CF3O3S)4(C19H19N3)2]Z = 1
Mr = 1302.12F(000) = 658
Triclinic, P1Dx = 1.731 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8793 (5) ÅCell parameters from 3859 reflections
b = 10.5542 (6) Åθ = 2.7–28.2°
c = 14.1620 (8) ŵ = 1.13 mm1
α = 103.357 (1)°T = 273 K
β = 94.115 (1)°Block, blue
γ = 102.742 (1)°0.33 × 0.22 × 0.16 mm
V = 1248.90 (12) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
6086 independent reflections
Radiation source: fine-focus sealed tube4109 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1111
Tmin = 0.707, Tmax = 0.840k = 1310
9293 measured reflectionsl = 1818
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)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.259H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0728P)2 + 10.1901P]
where P = (Fo2 + 2Fc2)/3
6086 reflections(Δ/σ)max < 0.001
352 parametersΔρmax = 1.52 e Å3
0 restraintsΔρmin = 2.48 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cu10.53776 (10)0.04467 (8)0.68715 (6)0.0336 (3)
N10.6323 (7)0.2005 (5)0.6661 (4)0.0317 (12)
N20.4854 (7)0.1285 (6)0.7313 (4)0.0348 (13)
N30.7136 (6)0.0320 (6)0.7993 (4)0.0297 (12)
C10.6124 (9)0.3014 (8)0.5847 (6)0.0432 (17)
H10.55230.29890.52890.052*
C20.6782 (9)0.4073 (8)0.5822 (7)0.049 (2)
H20.66210.47640.52540.059*
C30.7692 (9)0.4112 (8)0.6646 (7)0.052 (2)
H30.81240.48380.66470.062*
C40.7945 (9)0.3049 (8)0.7466 (6)0.0446 (18)
H40.85820.30380.80200.054*
C50.7259 (8)0.2022 (7)0.7462 (5)0.0347 (15)
C60.7397 (9)0.0843 (7)0.8333 (5)0.0366 (15)
H6A0.66340.10810.87600.044*
H6B0.84260.06150.87020.044*
C70.6546 (8)0.1268 (8)0.8735 (5)0.0366 (15)
H7A0.74110.18940.91820.044*
H7B0.58760.07770.91100.044*
C80.5639 (8)0.2029 (7)0.8215 (5)0.0312 (14)
C90.5518 (9)0.3295 (8)0.8604 (6)0.0422 (17)
H90.60730.37820.92090.051*
C100.4567 (10)0.3864 (8)0.8099 (6)0.0474 (19)
H100.44770.47340.83580.057*
C110.3760 (10)0.3116 (8)0.7210 (6)0.0458 (18)
H110.31020.34690.68610.055*
C120.3937 (9)0.1830 (7)0.6836 (6)0.0383 (16)
H120.33940.13330.62300.046*
C130.8563 (8)0.1022 (7)0.7620 (5)0.0346 (15)
H13A0.88700.03670.71180.041*
H13B0.82840.16870.73150.041*
C140.9936 (8)0.1705 (7)0.8390 (5)0.0330 (14)
C151.1037 (9)0.1011 (8)0.8615 (5)0.0387 (16)
H151.09440.01290.82680.046*
C161.2250 (9)0.1637 (10)0.9350 (6)0.0471 (19)
H161.29680.11670.94980.057*
C171.2425 (10)0.2934 (10)0.9867 (6)0.054 (2)
H171.32400.33351.03720.065*
C181.1369 (10)0.3654 (9)0.9634 (7)0.055 (2)
H181.14830.45430.99730.065*
C191.0152 (9)0.3026 (8)0.8891 (6)0.0451 (18)
H190.94620.35110.87250.054*
S20.2877 (2)0.14702 (18)0.48529 (12)0.0348 (4)
O10.3536 (6)0.1334 (5)0.5855 (4)0.0395 (12)
O20.3152 (7)0.0226 (5)0.4563 (4)0.0420 (12)
O30.3108 (8)0.2602 (6)0.4157 (4)0.0530 (15)
C200.0783 (10)0.1903 (11)0.4939 (6)0.058 (2)
F10.0413 (7)0.1110 (8)0.5697 (5)0.091 (2)
F20.0025 (6)0.1827 (8)0.4137 (5)0.089 (2)
F30.0329 (7)0.3163 (7)0.5020 (5)0.085 (2)
S30.2994 (2)0.7737 (2)0.84985 (14)0.0389 (4)
O40.3741 (7)0.8804 (5)0.8071 (4)0.0463 (13)
O50.4063 (7)0.7232 (7)0.9030 (4)0.0568 (16)
O60.1665 (7)0.7965 (6)0.8955 (4)0.0525 (15)
C210.2200 (8)0.6361 (9)0.7429 (6)0.0428 (18)
F40.1218 (6)0.6691 (6)0.6824 (4)0.0634 (14)
F50.1395 (7)0.5273 (5)0.7669 (4)0.0686 (16)
F60.3303 (7)0.5983 (5)0.6925 (4)0.0617 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0348 (5)0.0315 (5)0.0306 (4)0.0087 (3)0.0046 (3)0.0027 (3)
N10.034 (3)0.023 (3)0.030 (3)0.007 (2)0.000 (2)0.009 (2)
N20.037 (3)0.039 (3)0.027 (3)0.006 (2)0.000 (2)0.009 (2)
N30.026 (3)0.033 (3)0.022 (3)0.006 (2)0.005 (2)0.006 (2)
C10.042 (4)0.040 (4)0.045 (4)0.009 (3)0.001 (3)0.007 (3)
C20.039 (4)0.036 (4)0.060 (5)0.008 (3)0.004 (4)0.008 (4)
C30.039 (4)0.034 (4)0.078 (6)0.011 (3)0.001 (4)0.005 (4)
C40.042 (4)0.039 (4)0.053 (5)0.012 (3)0.007 (3)0.014 (3)
C50.026 (3)0.034 (4)0.041 (4)0.004 (3)0.002 (3)0.009 (3)
C60.038 (4)0.038 (4)0.038 (4)0.009 (3)0.000 (3)0.017 (3)
C70.031 (3)0.050 (4)0.026 (3)0.006 (3)0.002 (3)0.009 (3)
C80.034 (3)0.030 (3)0.024 (3)0.004 (3)0.004 (3)0.000 (2)
C90.038 (4)0.041 (4)0.040 (4)0.008 (3)0.004 (3)0.001 (3)
C100.051 (5)0.035 (4)0.055 (5)0.015 (3)0.000 (4)0.008 (3)
C110.051 (5)0.039 (4)0.045 (4)0.015 (4)0.000 (4)0.006 (3)
C120.040 (4)0.033 (4)0.047 (4)0.021 (3)0.004 (3)0.011 (3)
C130.038 (4)0.042 (4)0.024 (3)0.014 (3)0.003 (3)0.007 (3)
C140.035 (3)0.029 (3)0.031 (3)0.005 (3)0.003 (3)0.004 (3)
C150.039 (4)0.044 (4)0.038 (4)0.017 (3)0.008 (3)0.012 (3)
C160.028 (4)0.073 (6)0.043 (4)0.014 (4)0.001 (3)0.021 (4)
C170.037 (4)0.070 (6)0.040 (4)0.002 (4)0.000 (3)0.001 (4)
C180.043 (5)0.048 (5)0.061 (5)0.009 (4)0.003 (4)0.007 (4)
C190.036 (4)0.044 (4)0.048 (4)0.006 (3)0.004 (3)0.004 (3)
S20.0354 (9)0.0364 (9)0.0288 (8)0.0059 (7)0.0021 (6)0.0055 (7)
O10.031 (3)0.046 (3)0.035 (3)0.001 (2)0.012 (2)0.012 (2)
O20.056 (3)0.039 (3)0.033 (3)0.017 (2)0.005 (2)0.012 (2)
O30.072 (4)0.036 (3)0.042 (3)0.009 (3)0.004 (3)0.002 (2)
C200.042 (5)0.085 (7)0.042 (5)0.005 (5)0.013 (4)0.022 (5)
F10.064 (4)0.148 (7)0.075 (4)0.048 (4)0.027 (3)0.029 (4)
F20.041 (3)0.159 (7)0.072 (4)0.003 (3)0.011 (3)0.065 (4)
F30.067 (4)0.099 (5)0.077 (4)0.023 (3)0.009 (3)0.047 (4)
S30.0370 (9)0.0432 (10)0.0358 (9)0.0098 (8)0.0006 (7)0.0102 (8)
O40.048 (3)0.038 (3)0.049 (3)0.002 (2)0.006 (3)0.012 (2)
O50.050 (3)0.077 (4)0.050 (3)0.025 (3)0.008 (3)0.025 (3)
O60.046 (3)0.065 (4)0.051 (3)0.020 (3)0.017 (3)0.016 (3)
C210.029 (4)0.055 (5)0.045 (4)0.001 (3)0.005 (3)0.022 (4)
F40.056 (3)0.075 (4)0.054 (3)0.007 (3)0.014 (2)0.022 (3)
F50.078 (4)0.045 (3)0.079 (4)0.002 (3)0.016 (3)0.024 (3)
F60.068 (3)0.052 (3)0.062 (3)0.015 (3)0.023 (3)0.005 (2)
Geometric parameters (Å, º) top
Cu1—O11.997 (5)C13—C141.501 (9)
Cu1—N11.979 (5)C14—C191.374 (10)
Cu1—N21.959 (6)C14—C151.405 (10)
Cu1—N32.027 (5)C15—C161.374 (11)
N1—C11.347 (9)C16—C171.364 (13)
N1—C51.364 (9)C17—C181.397 (13)
N2—C121.326 (8)C18—C191.383 (11)
N2—C81.379 (8)S2—O31.426 (6)
N3—C61.475 (9)S2—O21.440 (5)
N3—C71.485 (9)S2—O11.458 (5)
N3—C131.516 (9)S2—C201.834 (9)
C1—C21.366 (11)C20—F11.311 (12)
C2—C31.385 (12)C20—F21.328 (9)
C3—C41.381 (12)C20—F31.336 (12)
C4—C51.357 (10)S3—O61.426 (6)
C5—C61.512 (10)S3—O51.434 (6)
C7—C81.519 (10)S3—O41.455 (6)
C8—C91.353 (10)S3—C211.811 (9)
C9—C101.386 (11)C21—F61.330 (9)
C10—C111.373 (11)C21—F41.334 (9)
C11—C121.386 (10)C21—F51.341 (9)
N2—Cu1—N1166.8 (2)C14—C13—N3114.6 (5)
N2—Cu1—O197.7 (2)C19—C14—C15118.3 (7)
N1—Cu1—O195.5 (2)C19—C14—C13120.9 (7)
N2—Cu1—N384.3 (2)C15—C14—C13120.8 (6)
N1—Cu1—N382.5 (2)C16—C15—C14119.9 (7)
O1—Cu1—N3173.7 (2)C17—C16—C15121.4 (8)
C1—N1—C5118.8 (6)C16—C17—C18119.5 (8)
C1—N1—Cu1127.8 (5)C19—C18—C17119.1 (8)
C5—N1—Cu1113.4 (4)C14—C19—C18121.7 (8)
C12—N2—C8118.3 (6)O3—S2—O2116.0 (3)
C12—N2—Cu1128.3 (5)O3—S2—O1114.4 (3)
C8—N2—Cu1113.3 (5)O2—S2—O1114.0 (3)
C6—N3—C7112.9 (5)O3—S2—C20103.9 (4)
C6—N3—C13111.9 (5)O2—S2—C20104.9 (4)
C7—N3—C13112.0 (5)O1—S2—C20101.5 (3)
C6—N3—Cu1105.4 (4)S2—O1—Cu1144.8 (3)
C7—N3—Cu1105.1 (4)F1—C20—F2108.4 (9)
C13—N3—Cu1108.9 (4)F1—C20—F3107.9 (8)
N1—C1—C2121.5 (7)F2—C20—F3107.3 (8)
C1—C2—C3119.6 (8)F1—C20—S2112.1 (6)
C4—C3—C2118.6 (7)F2—C20—S2110.5 (7)
C5—C4—C3119.8 (7)F3—C20—S2110.4 (7)
C4—C5—N1121.5 (7)O6—S3—O5115.9 (4)
C4—C5—C6124.1 (7)O6—S3—O4114.5 (4)
N1—C5—C6114.3 (6)O5—S3—O4114.0 (4)
N3—C6—C5109.6 (6)O6—S3—C21104.2 (4)
N3—C7—C8109.0 (5)O5—S3—C21103.5 (4)
C9—C8—N2121.7 (7)O4—S3—C21102.4 (3)
C9—C8—C7124.4 (6)F6—C21—F4107.7 (7)
N2—C8—C7113.9 (6)F6—C21—F5106.9 (7)
C8—C9—C10119.9 (7)F4—C21—F5106.6 (6)
C11—C10—C9118.6 (7)F6—C21—S3112.2 (5)
C10—C11—C12119.4 (7)F4—C21—S3111.3 (6)
N2—C12—C11122.2 (7)F5—C21—S3111.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O5i0.932.703.633176
C3—H3···O3ii0.932.633.286128
C11—H11···F6i0.932.603.251127
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1.
 

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