In the title compound, [Cu(C
10H
8N
2)
2](CF
3O
3S), the Cu
I ion is chelated by two 2,2′-bipyridine (bpy) ligands in a distorted tetrahedral coordination geometry. The average Cu—N bond length is 2.024 (3) Å. The interligand dihedral angle is 87.5 (11)°. Weak C—H
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O hydrogen bonding between the Cu
I complex cation and the trifluoromethanesulfonate anion stabilizes the crystal structure.
Supporting information
CCDC reference: 601277
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.036
- wR factor = 0.126
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C1 .. 5.03 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Cu1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C21
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.90
From the CIF: _reflns_number_total 5247
Count of symmetry unique reflns 2973
Completeness (_total/calc) 176.49%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2274
Fraction of Friedel pairs measured 0.765
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
Bis(2,2'-bipyridine-
κ2N,
N')copper(I) trifluoromethanesulfonate
top
Crystal data top
[Cu(C10H8N2)2](CF3O3S) | F(000) = 1064 |
Mr = 524.98 | Dx = 1.589 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4628 reflections |
a = 9.3749 (4) Å | θ = 2.4–21.1° |
b = 11.6692 (5) Å | µ = 1.15 mm−1 |
c = 20.0628 (9) Å | T = 273 K |
V = 2194.82 (17) Å3 | Needle, red |
Z = 4 | 0.30 × 0.15 × 0.07 mm |
Data collection top
Bruker SMART APEX-II diffractometer | 5247 independent reflections |
Radiation source: fine-focus sealed tube | 3736 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 27.9°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −12→12 |
Tmin = 0.810, Tmax = 0.920 | k = −15→15 |
22333 measured reflections | l = −26→26 |
Refinement top
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max = 0.001 |
5247 reflections | Δρmax = 0.25 e Å−3 |
298 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2274 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.003 (15) |
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 | 0.48037 (6) | 0.79231 (4) | 0.04420 (2) | 0.06712 (17) | |
S1 | 0.23922 (9) | 0.18283 (7) | 0.18194 (4) | 0.0512 (2) | |
N2 | 0.4967 (3) | 0.6210 (2) | 0.04215 (13) | 0.0515 (6) | |
N3 | 0.4642 (3) | 0.9071 (2) | −0.02973 (13) | 0.0528 (6) | |
N1 | 0.3315 (3) | 0.7546 (2) | 0.11465 (14) | 0.0488 (6) | |
N4 | 0.6327 (3) | 0.9053 (2) | 0.07602 (14) | 0.0526 (6) | |
C6 | 0.3206 (3) | 0.6421 (3) | 0.12805 (16) | 0.0426 (7) | |
C16 | 0.6406 (3) | 0.9998 (3) | 0.03764 (16) | 0.0455 (7) | |
C15 | 0.5454 (4) | 1.0019 (3) | −0.02057 (15) | 0.0455 (7) | |
C5 | 0.4174 (3) | 0.5676 (3) | 0.08866 (15) | 0.0439 (7) | |
C17 | 0.7347 (4) | 1.0860 (3) | 0.0529 (2) | 0.0623 (9) | |
H16 | 0.7381 | 1.1518 | 0.0268 | 0.075* | |
C19 | 0.8138 (5) | 0.9816 (4) | 0.1465 (2) | 0.0713 (11) | |
H18 | 0.8710 | 0.9739 | 0.1841 | 0.086* | |
C9 | 0.1523 (4) | 0.7913 (4) | 0.19577 (18) | 0.0652 (10) | |
H9 | 0.0957 | 0.8440 | 0.2183 | 0.078* | |
C18 | 0.8240 (5) | 1.0750 (4) | 0.1070 (2) | 0.0750 (11) | |
H17 | 0.8909 | 1.1315 | 0.1164 | 0.090* | |
C12 | 0.3709 (5) | 0.9898 (4) | −0.1292 (2) | 0.0726 (11) | |
H11 | 0.3111 | 0.9835 | −0.1660 | 0.087* | |
C4 | 0.4278 (4) | 0.4500 (3) | 0.09845 (19) | 0.0567 (9) | |
H4 | 0.3730 | 0.4145 | 0.1311 | 0.068* | |
C10 | 0.2496 (4) | 0.8269 (3) | 0.14893 (18) | 0.0589 (8) | |
H8 | 0.2588 | 0.9050 | 0.1408 | 0.071* | |
C14 | 0.5393 (5) | 1.0932 (3) | −0.06509 (18) | 0.0613 (9) | |
H13 | 0.5944 | 1.1583 | −0.0580 | 0.074* | |
C8 | 0.1403 (4) | 0.6763 (4) | 0.20852 (19) | 0.0653 (10) | |
H7 | 0.0739 | 0.6499 | 0.2394 | 0.078* | |
C11 | 0.3802 (5) | 0.9026 (4) | −0.0835 (2) | 0.0666 (10) | |
H10 | 0.3254 | 0.8372 | −0.0904 | 0.080* | |
C1 | 0.5824 (4) | 0.5565 (4) | 0.0045 (2) | 0.0666 (10) | |
H1 | 0.6360 | 0.5927 | −0.0283 | 0.080* | |
C20 | 0.7168 (4) | 0.8981 (3) | 0.12962 (19) | 0.0626 (9) | |
H19 | 0.7095 | 0.8337 | 0.1567 | 0.075* | |
C3 | 0.5190 (5) | 0.3862 (3) | 0.0597 (2) | 0.0706 (11) | |
H3 | 0.5279 | 0.3077 | 0.0665 | 0.085* | |
C13 | 0.4510 (5) | 1.0861 (4) | −0.1195 (2) | 0.0736 (11) | |
H12 | 0.4458 | 1.1465 | −0.1497 | 0.088* | |
C2 | 0.5963 (5) | 0.4395 (4) | 0.0114 (2) | 0.0738 (12) | |
H2 | 0.6568 | 0.3980 | −0.0163 | 0.089* | |
C7 | 0.2271 (4) | 0.5999 (3) | 0.17536 (17) | 0.0547 (8) | |
H20 | 0.2229 | 0.5219 | 0.1846 | 0.066* | |
O2 | 0.2715 (4) | 0.1935 (3) | 0.11246 (14) | 0.0854 (9) | |
O3 | 0.1526 (3) | 0.0865 (2) | 0.19883 (16) | 0.0715 (8) | |
O1 | 0.2018 (4) | 0.2881 (2) | 0.21280 (17) | 0.0825 (9) | |
C21 | 0.4110 (4) | 0.1491 (4) | 0.2187 (2) | 0.0697 (11) | |
F3 | 0.3992 (4) | 0.1398 (3) | 0.28431 (14) | 0.1081 (10) | |
F1 | 0.5044 (3) | 0.2301 (3) | 0.20818 (19) | 0.1198 (12) | |
F2 | 0.4626 (4) | 0.0543 (3) | 0.1966 (2) | 0.1366 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0841 (3) | 0.0489 (2) | 0.0684 (3) | −0.0210 (2) | 0.0107 (2) | 0.0110 (2) |
S1 | 0.0536 (4) | 0.0473 (4) | 0.0528 (5) | 0.0002 (3) | −0.0065 (4) | −0.0025 (3) |
N2 | 0.0560 (16) | 0.0519 (14) | 0.0465 (14) | −0.0078 (12) | 0.0083 (14) | −0.0037 (12) |
N3 | 0.0574 (16) | 0.0541 (15) | 0.0468 (15) | −0.0123 (13) | 0.0040 (13) | 0.0017 (12) |
N1 | 0.0605 (16) | 0.0413 (13) | 0.0446 (14) | −0.0051 (12) | 0.0012 (13) | 0.0003 (11) |
N4 | 0.0616 (16) | 0.0499 (15) | 0.0462 (15) | −0.0044 (13) | 0.0025 (13) | 0.0040 (12) |
C6 | 0.0455 (16) | 0.0423 (15) | 0.0399 (15) | −0.0036 (12) | −0.0029 (12) | 0.0023 (12) |
C16 | 0.0506 (17) | 0.0419 (15) | 0.0441 (16) | −0.0007 (13) | 0.0077 (14) | −0.0010 (13) |
C15 | 0.0495 (17) | 0.0433 (15) | 0.0438 (16) | −0.0051 (13) | 0.0065 (14) | −0.0001 (12) |
C5 | 0.0452 (16) | 0.0448 (16) | 0.0418 (16) | −0.0069 (13) | −0.0006 (13) | −0.0027 (13) |
C17 | 0.072 (2) | 0.0489 (17) | 0.066 (2) | −0.0104 (17) | −0.0016 (19) | −0.0035 (16) |
C19 | 0.074 (2) | 0.076 (3) | 0.064 (2) | 0.011 (2) | −0.022 (2) | −0.011 (2) |
C9 | 0.069 (2) | 0.068 (2) | 0.058 (2) | 0.020 (2) | 0.0019 (17) | −0.008 (2) |
C18 | 0.072 (2) | 0.073 (3) | 0.081 (3) | −0.013 (2) | −0.016 (2) | −0.015 (2) |
C12 | 0.075 (3) | 0.090 (3) | 0.053 (2) | −0.002 (2) | −0.010 (2) | 0.002 (2) |
C4 | 0.068 (2) | 0.0409 (16) | 0.061 (2) | −0.0050 (16) | 0.0077 (17) | 0.0051 (15) |
C10 | 0.075 (2) | 0.0505 (18) | 0.0510 (19) | 0.0081 (17) | −0.0045 (18) | −0.0053 (14) |
C14 | 0.074 (2) | 0.0528 (18) | 0.057 (2) | −0.0058 (18) | 0.0047 (17) | 0.0077 (16) |
C8 | 0.060 (2) | 0.081 (3) | 0.055 (2) | 0.0053 (19) | 0.0171 (17) | 0.0059 (19) |
C11 | 0.068 (2) | 0.072 (2) | 0.059 (2) | −0.018 (2) | −0.0009 (18) | −0.007 (2) |
C1 | 0.065 (2) | 0.078 (3) | 0.057 (2) | −0.010 (2) | 0.0137 (18) | −0.0016 (19) |
C20 | 0.078 (3) | 0.056 (2) | 0.054 (2) | 0.0093 (19) | 0.0021 (18) | 0.0047 (16) |
C3 | 0.086 (3) | 0.0530 (19) | 0.073 (2) | 0.008 (2) | 0.009 (2) | −0.0036 (18) |
C13 | 0.089 (3) | 0.072 (3) | 0.059 (2) | 0.005 (2) | −0.003 (2) | 0.020 (2) |
C2 | 0.073 (3) | 0.072 (3) | 0.076 (3) | 0.006 (2) | 0.013 (2) | −0.022 (2) |
C7 | 0.0568 (19) | 0.0517 (18) | 0.056 (2) | −0.0034 (16) | 0.0095 (16) | 0.0086 (15) |
O2 | 0.099 (2) | 0.104 (2) | 0.0529 (15) | −0.022 (2) | −0.0096 (15) | 0.0014 (16) |
O3 | 0.0583 (15) | 0.0596 (15) | 0.097 (2) | −0.0079 (12) | 0.0076 (14) | 0.0009 (14) |
O1 | 0.100 (2) | 0.0524 (14) | 0.095 (2) | 0.0218 (15) | −0.0154 (17) | −0.0109 (15) |
C21 | 0.055 (2) | 0.076 (3) | 0.078 (3) | 0.000 (2) | 0.001 (2) | 0.006 (2) |
F3 | 0.099 (2) | 0.147 (3) | 0.0782 (18) | 0.0016 (19) | −0.0288 (16) | 0.0301 (19) |
F1 | 0.0731 (18) | 0.142 (3) | 0.144 (3) | −0.0414 (19) | −0.0289 (17) | 0.038 (2) |
F2 | 0.087 (2) | 0.113 (2) | 0.210 (4) | 0.0500 (19) | −0.020 (2) | −0.042 (2) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.034 (3) | C9—C8 | 1.371 (6) |
Cu1—N2 | 2.005 (3) | C9—C10 | 1.374 (6) |
Cu1—N3 | 2.004 (3) | C9—H9 | 0.9300 |
Cu1—N4 | 2.046 (3) | C18—H17 | 0.9300 |
S1—O1 | 1.420 (3) | C12—C13 | 1.366 (6) |
S1—O3 | 1.427 (3) | C12—C11 | 1.372 (6) |
S1—O2 | 1.432 (3) | C12—H11 | 0.9300 |
S1—C21 | 1.814 (4) | C4—C3 | 1.375 (5) |
N2—C1 | 1.335 (5) | C4—H4 | 0.9300 |
N2—C5 | 1.346 (4) | C10—H8 | 0.9300 |
N3—C11 | 1.337 (5) | C14—C13 | 1.373 (6) |
N3—C15 | 1.356 (4) | C14—H13 | 0.9300 |
N1—C10 | 1.331 (5) | C8—C7 | 1.378 (5) |
N1—C6 | 1.345 (4) | C8—H7 | 0.9300 |
N4—C20 | 1.336 (5) | C11—H10 | 0.9300 |
N4—C16 | 1.347 (4) | C1—C2 | 1.379 (6) |
C6—C7 | 1.383 (5) | C1—H1 | 0.9300 |
C6—C5 | 1.484 (4) | C20—H19 | 0.9300 |
C16—C17 | 1.373 (4) | C3—C2 | 1.360 (6) |
C16—C15 | 1.470 (5) | C3—H3 | 0.9300 |
C15—C14 | 1.391 (5) | C13—H12 | 0.9300 |
C5—C4 | 1.390 (4) | C2—H2 | 0.9300 |
C17—C18 | 1.377 (6) | C7—H20 | 0.9300 |
C17—H16 | 0.9300 | C21—F2 | 1.286 (5) |
C19—C18 | 1.350 (6) | C21—F1 | 1.306 (5) |
C19—C20 | 1.375 (6) | C21—F3 | 1.325 (5) |
C19—H18 | 0.9300 | | |
| | | |
N3—Cu1—N2 | 131.04 (11) | C19—C18—C17 | 119.7 (4) |
N3—Cu1—N1 | 127.34 (12) | C19—C18—H17 | 120.2 |
N2—Cu1—N1 | 81.45 (10) | C17—C18—H17 | 120.2 |
N3—Cu1—N4 | 81.56 (11) | C13—C12—C11 | 118.7 (4) |
N2—Cu1—N4 | 126.56 (12) | C13—C12—H11 | 120.6 |
N1—Cu1—N4 | 113.67 (11) | C11—C12—H11 | 120.6 |
O1—S1—O3 | 115.94 (19) | C3—C4—C5 | 119.9 (3) |
O1—S1—O2 | 113.6 (2) | C3—C4—H4 | 120.1 |
O3—S1—O2 | 114.83 (19) | C5—C4—H4 | 120.1 |
O1—S1—C21 | 103.3 (2) | N1—C10—C9 | 123.0 (3) |
O3—S1—C21 | 103.71 (18) | N1—C10—H8 | 118.5 |
O2—S1—C21 | 103.1 (2) | C9—C10—H8 | 118.5 |
C1—N2—C5 | 117.6 (3) | C13—C14—C15 | 119.3 (4) |
C1—N2—Cu1 | 128.3 (3) | C13—C14—H13 | 120.3 |
C5—N2—Cu1 | 113.9 (2) | C15—C14—H13 | 120.3 |
C11—N3—C15 | 118.2 (3) | C9—C8—C7 | 119.6 (3) |
C11—N3—Cu1 | 128.0 (3) | C9—C8—H7 | 120.2 |
C15—N3—Cu1 | 113.7 (2) | C7—C8—H7 | 120.2 |
C10—N1—C6 | 118.1 (3) | N3—C11—C12 | 123.2 (4) |
C10—N1—Cu1 | 128.1 (2) | N3—C11—H10 | 118.4 |
C6—N1—Cu1 | 113.7 (2) | C12—C11—H10 | 118.4 |
C20—N4—C16 | 118.7 (3) | N2—C1—C2 | 124.0 (4) |
C20—N4—Cu1 | 128.5 (3) | N2—C1—H1 | 118.0 |
C16—N4—Cu1 | 112.8 (2) | C2—C1—H1 | 118.0 |
N1—C6—C7 | 122.2 (3) | N4—C20—C19 | 122.9 (4) |
N1—C6—C5 | 114.8 (3) | N4—C20—H19 | 118.5 |
C7—C6—C5 | 123.0 (3) | C19—C20—H19 | 118.5 |
N4—C16—C17 | 120.5 (3) | C2—C3—C4 | 119.2 (4) |
N4—C16—C15 | 115.8 (3) | C2—C3—H3 | 120.4 |
C17—C16—C15 | 123.7 (3) | C4—C3—H3 | 120.4 |
N3—C15—C14 | 121.0 (3) | C12—C13—C14 | 119.6 (4) |
N3—C15—C16 | 115.8 (3) | C12—C13—H12 | 120.2 |
C14—C15—C16 | 123.2 (3) | C14—C13—H12 | 120.2 |
N2—C5—C4 | 121.1 (3) | C3—C2—C1 | 118.3 (4) |
N2—C5—C6 | 115.8 (3) | C3—C2—H2 | 120.9 |
C4—C5—C6 | 123.1 (3) | C1—C2—H2 | 120.9 |
C16—C17—C18 | 119.9 (4) | C8—C7—C6 | 118.4 (3) |
C16—C17—H16 | 120.1 | C8—C7—H20 | 120.8 |
C18—C17—H16 | 120.1 | C6—C7—H20 | 120.8 |
C18—C19—C20 | 118.3 (4) | F2—C21—F1 | 108.3 (4) |
C18—C19—H18 | 120.9 | F2—C21—F3 | 107.7 (4) |
C20—C19—H18 | 120.9 | F1—C21—F3 | 106.0 (4) |
C8—C9—C10 | 118.6 (3) | F2—C21—S1 | 112.3 (3) |
C8—C9—H9 | 120.7 | F1—C21—S1 | 111.9 (3) |
C10—C9—H9 | 120.7 | F3—C21—S1 | 110.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.93 | 2.45 | 3.359 (5) | 165 |
C8—H7···O3ii | 0.93 | 2.57 | 3.478 (5) | 166 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x, y+1/2, −z+1/2. |