Bis(2,2′-bipyridine-κ2N,N′)copper(I) trifluoro­methane­sulfonate

Tomislav, P.

doi:10.1107/S1600536806006222

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Bis(2,2′-bipyridine-κ²N,N′)copper(I) trifluoromethanesulfonate

P. Tomislav

In the title compound, [Cu(C₁₀H₈N₂)₂](CF₃O₃S), 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

O hydrogen bonding between the Cu^I complex cation and the trifluoromethanesulfonate anion stabilizes the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006222/xu6114sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006222/xu6114Isup2.hkl Contains datablock I

CCDC reference: 601277

checkCIF report

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

Computing details top

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
M_r = 524.98	D_x = 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	R_int = 0.039
φ and ω scans	θ_max = 27.9°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −12→12
T_min = 0.810, T_max = 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(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max = 0.001
5247 reflections	Δρ_max = 0.25 e Å⁻³
298 parameters	Δρ_min = −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	U_iso*/U_eq
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.

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