Two coordination modes of CuII in a binuclear complex with N-(pyridin-2-yl­carbon­yl)pyridine-2-carboxamidate ligands

Campos-Gaxiola, J.J.; Morales-Morales, D.; Höpfl, H.; Parra-Hake, M.; Reyes-Martínez, R.

doi:10.1107/S1600536812038330

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages m1280-m1281

https://doi.org/10.1107/S1600536812038330

Open

access

Two coordination modes of Cu^II in a binuclear complex with N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate ligands

José J. Campos-Gaxiola,^a ^* David Morales-Morales,^b Herbert Höpfl,^c Miguel Parra-Hake ^d and Reyna Reyes-Martínez ^b

^aFacultad de Ingeniería Mochis, Universidad Autónoma de Sinaloa, Fuente de Poseidón y Prol. Ángel Flores, 81223 Los Mochis, Sinaloa, México, ^bInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, D.F., 04510, México, ^cCentro de Investigaciones Químicas, Universidad Autónoma del estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, México, and ^dCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500 Tijuana, BC, México
^*Correspondence e-mail: gaxiolajose@yahoo.com.mx

(Received 2 August 2012; accepted 6 September 2012; online 19 September 2012)

In the title dinuclear complex, (acetonitrile-1κN)[μ-N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidato-1:2κ⁵N,N′,N′′:O,O′][N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidato-2κ³N,N′,N′′]bis(trifluoromethanesulfonato-1κO)dicopper(II), [Cu₂(C₁₂H₈N₃O₂)₂(CF₃O₃S)₂(CH₃CN)], one of the Cu^II ions is five-coordinated in a distorted square-pyramidal N₃O₂ environment provided by two N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate (bpca) ligands, while the second Cu^II ion is six-coordinated in a distorted octahedral N₄O₂ environment provided by one bpca ligand, two trifluoromethansulfonate ligands and one acetonitrile molecule. Weak intermolecular C—H⋯O and C—H⋯F hydrogen bonds and π–π stacking interactions with centroid–centroid distances of 3.6799 (15) and 3.8520 (16) Å stabilize the crystal packing and lead to a three-dimensional network.

Related literature

For complexes of divalent metal ions with the N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate (bpca) ligand, see: Chowdhury et al. (2007 ); Folgado et al. (1988 ); Ha (2010 , 2011 ); Halder et al. (2010 ); Miguel et al. (2009 ). For complexes of trivalent metal ions with the bpca ligand, see: Li et al. (2011 ); Sugimoto et al. (2002 ); Wocadlo et al. (1993 ). For electrochemical and magnetic studies for example complexes of Cu(II), see: Cangussu de Castro Gomes et al. (2008 ); Kajiwara et al. (2002 ). For the synthesis of the ligand, see: Larter et al. (1998 ).

Experimental

Crystal data

[Cu₂(C₁₂H₈N₃O₂)₂(CF₃O₃S)₂(C₂H₃N)]
M_r = 918.70
Triclinic, $[P \overline 1]$
a = 8.9726 (7) Å
b = 10.0569 (8) Å
c = 18.3689 (15) Å
α = 82.573 (1)°
β = 83.802 (1)°
γ = 82.222 (1)°
V = 1621.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.55 mm⁻¹
T = 100 K
0.32 × 0.24 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.638, T_max = 0.768
15254 measured reflections
5686 independent reflections
5292 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.087
S = 1.04
5686 reflections
497 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O9ⁱ	0.95	2.57	3.448 (3)	154
C4—H4⋯O1ⁱⁱ	0.95	2.53	3.210 (4)	128
C10—H10⋯F5ⁱⁱⁱ	0.95	2.54	3.239 (3)	130
C21—H21⋯O1^iv	0.95	2.48	3.257 (3)	140
C21—H21⋯O2^iv	0.95	2.37	3.203 (3)	147
C22—H22⋯O10^v	0.95	2.48	3.400 (3)	163
Symmetry codes: (i) x+1, y-1, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y+2, -z+1; (iv) -x+2, -y+1, -z+1; (v) x+1, y, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038330/wm2669sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038330/wm2669Isup2.hkl

checkCIF report

Comment top

N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate (bpca) is a rigid tridentate ligand that can act as a bridging ligand to produce supramolecular structures based on organic-inorganic coordination frameworks (Halder et al., 2010). This ligand exhibits various coordination modes. It can also appear as a regular tridentate chelating ligand via its two pyridine and one amine N atoms, or in a bidentate manner through the carboxyl groups. The bpca ligand forms coordination complexes with a large number of divalent metal ions, e.g. Pd(II) (Ha, 2010; Miguel et al., 2009), Pt(II) (Ha, 2011), Cu(II) (Folgado et al., 1988; Chowdhury et al., 2007), or with trivalent metals ions, e.g. Fe(III) (Wocadlo et al., 1993; Li et al., 2011), Cr(III) (Kajiwara et al., 2002), Co(III), Re(III) (Sugimoto et al., 2002)]. Mono and multinuclear complexes with bpca have been the subject of various electrochemical and magnetic studies, for example of complexes of Cu(II) (Cangussu de Castro Gomes et al., 2008; Chowdhury et al., 2007) and Co(III) (Kajiwara et al., 2002). In this context we report here the crystal structure for the dinuclear copper complex [Cu₂(C₁₂H₈N₃O₂)₂(CF₃SO₃)₂(CH₃CN)], or [(bpca)Cu(µ-bpca)Cu(OSO₂CF₃)₂(NCCH₃)]. An ORTEP-style plot of the molecular structure including the atom numbering is shown in Figure 1.

The above mentioned complex presents the copper(II) ion Cu1 in a five-coordinate environment in a somewhat distorted square pyramidal geometry. The coordination includes two bpca ligands. One ligand acts as a tridentate N,N'N''-chelate through two pyridine nitrogen atoms (Cu—N1 = 1.978 (2) and Cu—N3 = 1.988 (2) Å) and one amide nitrogen atom in basal positions (Cu—N2 = 1.922 (2) Å); the forth basal position is occupied by one carbonyl O atom (O4) from the bridging ligand with a Cu—O distance of 1.977 (18) while the second carbonyl O atom (O3) is at the apical site at a distance of 2.2452 (18). The six-coordinate Cu2 ion is found in a distorted octahedral geometry, defined by the N atoms of the bridging bpca ligand and one acetonitrile molecule in equatorial positions and two trifluoromethansulfonate O atoms with distances Cu—O of 2.439 (2) and 2.482 (2) Å in axial positions. The angles between the copper atoms and the bpca ligands vary in the range of 81.49 (9) - 82.83 (9) ° evidencing the small bite angle of the corresponding five membered chelate rings.

In the crystal lattice, the dinuclear units are packed through intermolecular C—H···A (A = O, F) hydrogen bonds (Table 1) between the pyridine ring hydrogen atoms and the carbonyl oxygen atoms (O1, O2) of the bpca ligand, the sulfonyl oxygen (O9, O10) and the fluor atom (F5) of the trifluoromethansulfonate ligands. The pyridine rings interact also via π–π stacking interactions, with Cg—Cg distances of 3.6799 (15) Å for the interaction between the tridentate bpca ligands, and of 3.8520 (16) Å for the interactions between the bridging bpca ligands (Fig. 2).

Related literature top

For complexes of divalent metal ions with the N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate (bpca) ligand, see: Chowdhury et al. (2007); Folgado et al. (1988); Ha (2010, 2011); Halder et al. (2010); Miguel et al. (2009). For complexes of trivalent metal ions with the bpca ligand, see: Li et al. (2011); Sugimoto et al. (2002); Wocadlo et al. (1993). For electrochemical and magnetic studies for example complexes of Cu(II), see: Cangussu de Castro Gomes et al. (2008); Kajiwara et al. (2002). For the synthesis of the ligand, see: Larter et al. (1998).

Experimental top

The starting material trans-(±)-2,4,5-tris(pyridine-2-yl)-2-imidazoline was synthesized according to a previously reported procedure (Larter et al., 1998). For the preparation of the title compound, a mixture of trans-(±)-2,4,5-tris(pyridine-2-yl)-2-imidazoline (0.086 g, 0.1382 mmol) and Cu(OSO₂CF₃)₂ (0.050 g, 0.1382 mmol) was dissolved in acetonitrile (5 ml) and stirred for 24 h at room temperature to afford a green solution. The product was crystallized at room temperature by gas phase diffusion of diethyl ether into the reaction mixture, producing green crystals which were separated and further dried under vacuum. Yield: 24%. IR (KBr): 3082, 3030, 1707, 1672, 1626, 1587, 1544, 1462, 1380, 1323, 1264, 1239, 1144, 1013, 740 cm^-1. MS [FAB⁺, m/z (%)]: 729 (2) [(M+H)-OSO₂CF₃—NCCH₃]⁺.

Structure description top

For complexes of divalent metal ions with the N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate (bpca) ligand, see: Chowdhury et al. (2007); Folgado et al. (1988); Ha (2010, 2011); Halder et al. (2010); Miguel et al. (2009). For complexes of trivalent metal ions with the bpca ligand, see: Li et al. (2011); Sugimoto et al. (2002); Wocadlo et al. (1993). For electrochemical and magnetic studies for example complexes of Cu(II), see: Cangussu de Castro Gomes et al. (2008); Kajiwara et al. (2002). For the synthesis of the ligand, see: Larter et al. (1998).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 40% probability level.
	Fig. 2. A part of the crystal packing of the title compound, showing intermolecular C—H···O and π···π interactions. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

(Acetonitrile-1κN)[µ-N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidato-1:2κ⁵N,N',N'':O,O'][N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidato- 2κ³N,N',N'']bis(trifluoromethanesulfonato-1κO)dicopper(II) top

Crystal data top

[Cu₂(C₁₂H₈N₃O₂)₂(CF₃SO₃)₂(C₂H₃N)]	Z = 2
M_r = 918.70	F(000) = 920
Triclinic, P1	D_x = 1.882 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9726 (7) Å	Cell parameters from 6358 reflections
b = 10.0569 (8) Å	θ = 2.2–28.3°
c = 18.3689 (15) Å	µ = 1.55 mm⁻¹
α = 82.573 (1)°	T = 100 K
β = 83.802 (1)°	Rectangular prism, green
γ = 82.222 (1)°	0.32 × 0.24 × 0.18 mm
V = 1621.6 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5686 independent reflections
Radiation source: fine-focus sealed tube	5292 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.638, T_max = 0.768	k = −11→11
15254 measured reflections	l = −21→21

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0451P)² + 2.0646P] where P = (F_o² + 2F_c²)/3
5686 reflections	(Δ/σ)_max = 0.008
497 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Cu₂(C₁₂H₈N₃O₂)₂(CF₃SO₃)₂(C₂H₃N)]	γ = 82.222 (1)°
M_r = 918.70	V = 1621.6 (2) Å³
Triclinic, P1	Z = 2
a = 8.9726 (7) Å	Mo Kα radiation
b = 10.0569 (8) Å	µ = 1.55 mm⁻¹
c = 18.3689 (15) Å	T = 100 K
α = 82.573 (1)°	0.32 × 0.24 × 0.18 mm
β = 83.802 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5686 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5292 reflections with I > 2σ(I)
T_min = 0.638, T_max = 0.768	R_int = 0.024
15254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.04	Δρ_max = 0.83 e Å⁻³
5686 reflections	Δρ_min = −0.50 e Å⁻³
497 parameters

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	0.84461 (3)	0.49089 (3)	0.586455 (16)	0.01596 (10)
Cu2	0.71274 (4)	0.65971 (3)	0.851929 (17)	0.02035 (10)
S1	0.90238 (8)	0.33964 (7)	0.90897 (4)	0.02539 (16)
S2	0.55073 (7)	0.99281 (7)	0.74959 (4)	0.02062 (15)
F1	0.7268 (3)	0.1888 (2)	0.99513 (11)	0.0517 (6)
F2	0.8668 (3)	0.08502 (19)	0.91195 (12)	0.0532 (6)
F3	0.6749 (2)	0.2241 (2)	0.88165 (13)	0.0564 (6)
F4	0.8208 (2)	1.0523 (2)	0.76493 (11)	0.0508 (5)
F5	0.7233 (2)	1.15490 (17)	0.66873 (11)	0.0381 (4)
F6	0.8107 (2)	0.94594 (19)	0.67342 (11)	0.0416 (5)
N1	0.9880 (2)	0.3263 (2)	0.60772 (11)	0.0176 (4)
N2	0.8212 (2)	0.4073 (2)	0.50069 (11)	0.0170 (4)
N3	0.6971 (2)	0.6358 (2)	0.54179 (11)	0.0175 (4)
N4	0.5243 (2)	0.5723 (2)	0.85181 (12)	0.0197 (5)
N5	0.7535 (2)	0.5968 (2)	0.75566 (12)	0.0201 (5)
N6	0.9188 (2)	0.7201 (2)	0.82471 (12)	0.0191 (5)
N7	0.6692 (3)	0.7400 (2)	0.94561 (12)	0.0237 (5)
O1	0.8791 (2)	0.20122 (18)	0.45319 (10)	0.0241 (4)
O2	0.6910 (2)	0.44173 (19)	0.39529 (10)	0.0236 (4)
O3	0.6675 (2)	0.45898 (18)	0.68097 (9)	0.0202 (4)
O4	0.9287 (2)	0.59552 (18)	0.65287 (10)	0.0200 (4)
O5	0.7980 (2)	0.4528 (2)	0.92880 (11)	0.0309 (5)
O6	1.0187 (2)	0.2967 (2)	0.95778 (12)	0.0374 (5)
O7	0.9513 (2)	0.3449 (2)	0.83152 (11)	0.0367 (5)
O8	0.5841 (3)	0.8840 (2)	0.80548 (13)	0.0442 (6)
O9	0.4725 (2)	1.1139 (2)	0.77653 (12)	0.0339 (5)
O10	0.4920 (2)	0.9585 (2)	0.68607 (12)	0.0342 (5)
C1	1.0716 (3)	0.2935 (3)	0.66516 (15)	0.0228 (6)
H1	1.0666	0.3552	0.7006	0.027*
C2	1.1649 (3)	0.1725 (3)	0.67427 (16)	0.0264 (6)
H2	1.2239	0.1514	0.7152	0.032*
C3	1.1708 (3)	0.0831 (3)	0.62301 (15)	0.0246 (6)
H3	1.2344	−0.0005	0.6281	0.030*
C4	1.0842 (3)	0.1154 (3)	0.56420 (15)	0.0211 (6)
H4	1.0867	0.0546	0.5284	0.025*
C5	0.9936 (3)	0.2380 (3)	0.55840 (14)	0.0176 (5)
C6	0.8920 (3)	0.2789 (2)	0.49648 (14)	0.0175 (5)
C7	0.7229 (3)	0.4747 (3)	0.45235 (14)	0.0181 (5)
C8	0.6495 (3)	0.6052 (3)	0.47920 (13)	0.0171 (5)
C9	0.5377 (3)	0.6875 (3)	0.44324 (14)	0.0201 (5)
H9	0.5069	0.6650	0.3989	0.024*
C10	0.4715 (3)	0.8028 (3)	0.47282 (15)	0.0228 (6)
H10	0.3949	0.8616	0.4489	0.027*
C11	0.5179 (3)	0.8319 (3)	0.53755 (15)	0.0223 (6)
H11	0.4716	0.9097	0.5594	0.027*
C12	0.6315 (3)	0.7474 (3)	0.57013 (14)	0.0207 (6)
H12	0.6645	0.7690	0.6141	0.025*
C13	0.4100 (3)	0.5647 (3)	0.90416 (15)	0.0232 (6)
H13	0.4128	0.6060	0.9476	0.028*
C14	0.2871 (3)	0.4986 (3)	0.89746 (15)	0.0243 (6)
H14	0.2068	0.4951	0.9356	0.029*
C15	0.2829 (3)	0.4384 (3)	0.83506 (15)	0.0258 (6)
H15	0.1990	0.3937	0.8291	0.031*
C16	0.4027 (3)	0.4434 (3)	0.78055 (15)	0.0230 (6)
H16	0.4031	0.4012	0.7371	0.028*
C17	0.5205 (3)	0.5109 (3)	0.79105 (14)	0.0187 (5)
C18	0.6545 (3)	0.5187 (3)	0.73564 (14)	0.0187 (5)
C19	0.8827 (3)	0.6220 (2)	0.71644 (13)	0.0166 (5)
C20	0.9778 (3)	0.6941 (2)	0.75634 (14)	0.0176 (5)
C21	1.1151 (3)	0.7301 (3)	0.72523 (14)	0.0201 (5)
H21	1.1531	0.7101	0.6770	0.024*
C22	1.1966 (3)	0.7964 (3)	0.76622 (15)	0.0232 (6)
H22	1.2918	0.8230	0.7466	0.028*
C23	1.1370 (3)	0.8229 (3)	0.83589 (15)	0.0252 (6)
H23	1.1909	0.8681	0.8649	0.030*
C24	0.9979 (3)	0.7832 (3)	0.86351 (15)	0.0233 (6)
H24	0.9579	0.8018	0.9117	0.028*
C25	0.6605 (3)	0.7991 (3)	0.99484 (16)	0.0266 (6)
C26	0.6546 (4)	0.8740 (3)	1.05813 (17)	0.0329 (7)
H26A	0.7570	0.8726	1.0724	0.049*
H26B	0.5919	0.8321	1.0995	0.049*
H26C	0.6110	0.9677	1.0451	0.049*
C27	0.7879 (4)	0.2023 (3)	0.92485 (18)	0.0374 (7)
C28	0.7356 (3)	1.0402 (3)	0.71278 (16)	0.0254 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01840 (17)	0.01472 (17)	0.01487 (17)	−0.00005 (12)	−0.00226 (12)	−0.00360 (12)
Cu2	0.02125 (18)	0.02642 (19)	0.01445 (17)	−0.00578 (14)	−0.00002 (12)	−0.00476 (13)
S1	0.0219 (3)	0.0308 (4)	0.0235 (4)	−0.0026 (3)	−0.0030 (3)	−0.0034 (3)
S2	0.0196 (3)	0.0222 (3)	0.0200 (3)	−0.0035 (3)	−0.0015 (3)	−0.0011 (3)
F1	0.0657 (14)	0.0437 (12)	0.0441 (12)	−0.0192 (10)	0.0183 (10)	−0.0058 (9)
F2	0.0772 (16)	0.0270 (10)	0.0535 (13)	0.0020 (10)	−0.0004 (11)	−0.0113 (9)
F3	0.0441 (12)	0.0621 (14)	0.0711 (15)	−0.0188 (11)	−0.0180 (11)	−0.0151 (12)
F4	0.0324 (11)	0.0827 (16)	0.0427 (11)	−0.0211 (10)	−0.0145 (9)	−0.0035 (11)
F5	0.0342 (10)	0.0265 (9)	0.0497 (11)	−0.0080 (8)	0.0021 (8)	0.0093 (8)
F6	0.0282 (10)	0.0393 (11)	0.0543 (12)	−0.0005 (8)	0.0117 (8)	−0.0110 (9)
N1	0.0170 (11)	0.0177 (11)	0.0173 (11)	−0.0013 (9)	−0.0005 (8)	−0.0009 (9)
N2	0.0201 (11)	0.0147 (11)	0.0160 (10)	0.0000 (9)	−0.0023 (8)	−0.0034 (8)
N3	0.0207 (11)	0.0159 (11)	0.0153 (10)	−0.0013 (9)	0.0000 (8)	−0.0012 (8)
N4	0.0212 (11)	0.0215 (11)	0.0160 (11)	−0.0038 (9)	−0.0004 (9)	−0.0003 (9)
N5	0.0198 (11)	0.0267 (12)	0.0150 (11)	−0.0057 (9)	0.0001 (9)	−0.0051 (9)
N6	0.0200 (11)	0.0203 (11)	0.0168 (11)	−0.0011 (9)	−0.0036 (9)	−0.0017 (9)
N7	0.0284 (13)	0.0250 (12)	0.0177 (12)	−0.0045 (10)	0.0005 (9)	−0.0036 (10)
O1	0.0318 (11)	0.0180 (9)	0.0230 (10)	0.0017 (8)	−0.0063 (8)	−0.0066 (8)
O2	0.0283 (10)	0.0242 (10)	0.0186 (10)	0.0030 (8)	−0.0063 (8)	−0.0070 (8)
O3	0.0218 (9)	0.0218 (9)	0.0180 (9)	−0.0059 (8)	0.0003 (7)	−0.0037 (8)
O4	0.0204 (9)	0.0214 (9)	0.0194 (9)	−0.0044 (7)	0.0000 (7)	−0.0066 (7)
O5	0.0397 (12)	0.0265 (11)	0.0255 (11)	−0.0026 (9)	−0.0018 (9)	−0.0025 (8)
O6	0.0278 (11)	0.0557 (15)	0.0284 (11)	−0.0046 (10)	−0.0080 (9)	0.0005 (10)
O7	0.0315 (12)	0.0515 (14)	0.0247 (11)	−0.0044 (10)	0.0033 (9)	−0.0016 (10)
O8	0.0366 (13)	0.0437 (14)	0.0445 (14)	−0.0016 (11)	−0.0006 (10)	0.0184 (11)
O9	0.0334 (12)	0.0347 (12)	0.0344 (12)	−0.0005 (9)	0.0019 (9)	−0.0150 (9)
O10	0.0265 (11)	0.0491 (13)	0.0312 (11)	−0.0105 (10)	0.0000 (9)	−0.0169 (10)
C1	0.0234 (14)	0.0253 (14)	0.0195 (13)	−0.0017 (11)	−0.0030 (11)	−0.0023 (11)
C2	0.0222 (14)	0.0305 (16)	0.0252 (14)	0.0008 (12)	−0.0060 (11)	0.0009 (12)
C3	0.0209 (14)	0.0205 (14)	0.0289 (15)	0.0035 (11)	−0.0001 (11)	0.0024 (11)
C4	0.0194 (13)	0.0186 (13)	0.0242 (14)	−0.0009 (10)	0.0007 (11)	−0.0022 (11)
C5	0.0172 (13)	0.0169 (12)	0.0178 (13)	−0.0043 (10)	0.0023 (10)	0.0006 (10)
C6	0.0190 (13)	0.0161 (13)	0.0167 (12)	−0.0018 (10)	0.0008 (10)	−0.0017 (10)
C7	0.0180 (13)	0.0180 (13)	0.0171 (13)	−0.0025 (10)	0.0018 (10)	−0.0004 (10)
C8	0.0194 (13)	0.0164 (13)	0.0150 (12)	−0.0027 (10)	−0.0003 (10)	−0.0005 (10)
C9	0.0206 (13)	0.0205 (13)	0.0183 (13)	−0.0024 (11)	−0.0005 (10)	−0.0002 (10)
C10	0.0219 (14)	0.0209 (14)	0.0224 (14)	0.0013 (11)	0.0005 (11)	0.0027 (11)
C11	0.0262 (14)	0.0150 (13)	0.0229 (14)	0.0010 (11)	0.0046 (11)	−0.0013 (10)
C12	0.0267 (14)	0.0173 (13)	0.0182 (13)	−0.0008 (11)	−0.0017 (11)	−0.0047 (10)
C13	0.0265 (14)	0.0235 (14)	0.0178 (13)	−0.0005 (11)	0.0014 (11)	−0.0011 (11)
C14	0.0231 (14)	0.0257 (14)	0.0215 (14)	−0.0013 (11)	0.0031 (11)	0.0012 (11)
C15	0.0226 (14)	0.0289 (15)	0.0258 (15)	−0.0089 (12)	0.0003 (11)	0.0017 (12)
C16	0.0258 (14)	0.0237 (14)	0.0196 (13)	−0.0045 (11)	−0.0020 (11)	−0.0015 (11)
C17	0.0203 (13)	0.0180 (13)	0.0169 (13)	−0.0009 (10)	−0.0016 (10)	0.0004 (10)
C18	0.0203 (13)	0.0182 (13)	0.0169 (13)	−0.0008 (10)	−0.0038 (10)	0.0010 (10)
C19	0.0197 (13)	0.0141 (12)	0.0152 (12)	0.0006 (10)	−0.0024 (10)	−0.0010 (10)
C20	0.0211 (13)	0.0147 (12)	0.0162 (12)	0.0015 (10)	−0.0040 (10)	−0.0007 (10)
C21	0.0212 (13)	0.0194 (13)	0.0192 (13)	−0.0004 (10)	−0.0031 (10)	−0.0019 (10)
C22	0.0208 (14)	0.0225 (14)	0.0266 (14)	−0.0054 (11)	−0.0036 (11)	0.0000 (11)
C23	0.0303 (15)	0.0233 (14)	0.0245 (14)	−0.0070 (12)	−0.0085 (12)	−0.0028 (11)
C24	0.0273 (15)	0.0250 (14)	0.0191 (13)	−0.0046 (11)	−0.0056 (11)	−0.0035 (11)
C25	0.0262 (15)	0.0247 (15)	0.0270 (16)	−0.0023 (12)	0.0002 (12)	0.0009 (13)
C26	0.0398 (18)	0.0337 (17)	0.0271 (16)	−0.0023 (14)	−0.0038 (13)	−0.0124 (13)
C27	0.0411 (19)	0.0339 (18)	0.0372 (18)	−0.0062 (14)	0.0011 (15)	−0.0063 (14)
C28	0.0231 (14)	0.0252 (15)	0.0277 (15)	−0.0035 (12)	−0.0039 (11)	−0.0002 (12)

Geometric parameters (Å, º) top

Cu1—N2	1.922 (2)	C1—C2	1.382 (4)
Cu1—O4	1.9772 (18)	C1—H1	0.9500
Cu1—N1	1.978 (2)	C2—C3	1.376 (4)
Cu1—N3	1.988 (2)	C2—H2	0.9500
Cu1—O3	2.2452 (18)	C3—C4	1.378 (4)
Cu2—N5	1.936 (2)	C3—H3	0.9500
Cu2—N7	1.973 (2)	C4—C5	1.381 (4)
Cu2—N4	2.008 (2)	C4—H4	0.9500
Cu2—N6	2.016 (2)	C5—C6	1.515 (4)
Cu2—O5	2.439 (2)	C7—C8	1.505 (3)
S1—O5	1.432 (2)	C8—C9	1.380 (4)
S1—O6	1.435 (2)	C9—C10	1.378 (4)
S1—O7	1.439 (2)	C9—H9	0.9500
S1—C27	1.807 (3)	C10—C11	1.379 (4)
S2—O8	1.424 (2)	C10—H10	0.9500
S2—O10	1.430 (2)	C11—C12	1.373 (4)
S2—O9	1.439 (2)	C11—H11	0.9500
S2—C28	1.823 (3)	C12—H12	0.9500
F1—C27	1.344 (4)	C13—C14	1.387 (4)
F2—C27	1.326 (4)	C13—H13	0.9500
F3—C27	1.332 (4)	C14—C15	1.370 (4)
F4—C28	1.316 (3)	C14—H14	0.9500
F5—C28	1.320 (3)	C15—C16	1.389 (4)
F6—C28	1.332 (3)	C15—H15	0.9500
N1—C5	1.341 (3)	C16—C17	1.374 (4)
N1—C1	1.341 (3)	C16—H16	0.9500
N2—C6	1.367 (3)	C17—C18	1.493 (4)
N2—C7	1.371 (3)	C19—C20	1.493 (4)
N3—C12	1.335 (3)	C20—C21	1.375 (4)
N3—C8	1.354 (3)	C21—C22	1.388 (4)
N4—C13	1.331 (4)	C21—H21	0.9500
N4—C17	1.349 (3)	C22—C23	1.377 (4)
N5—C19	1.333 (3)	C22—H22	0.9500
N5—C18	1.370 (3)	C23—C24	1.385 (4)
N6—C24	1.327 (3)	C23—H23	0.9500
N6—C20	1.353 (3)	C24—H24	0.9500
N7—C25	1.135 (4)	C25—C26	1.457 (4)
O1—C6	1.209 (3)	C26—H26A	0.9800
O2—C7	1.213 (3)	C26—H26B	0.9800
O3—C18	1.222 (3)	C26—H26C	0.9800
O4—C19	1.246 (3)

N2—Cu1—O4	160.54 (8)	O2—C7—C8	120.4 (2)
N2—Cu1—N1	82.83 (9)	N2—C7—C8	110.6 (2)
O4—Cu1—N1	94.22 (8)	N3—C8—C9	121.9 (2)
N2—Cu1—N3	82.65 (9)	N3—C8—C7	116.0 (2)
O4—Cu1—N3	99.18 (8)	C9—C8—C7	122.1 (2)
N1—Cu1—N3	165.44 (9)	C10—C9—C8	118.7 (2)
N2—Cu1—O3	115.15 (8)	C10—C9—H9	120.6
O4—Cu1—O3	84.30 (7)	C8—C9—H9	120.6
N1—Cu1—O3	99.70 (8)	C9—C10—C11	119.2 (2)
N3—Cu1—O3	87.33 (8)	C9—C10—H10	120.4
N5—Cu2—N7	175.01 (10)	C11—C10—H10	120.4
N5—Cu2—N4	81.63 (9)	C12—C11—C10	119.4 (2)
N7—Cu2—N4	100.19 (9)	C12—C11—H11	120.3
N5—Cu2—N6	81.49 (9)	C10—C11—H11	120.3
N7—Cu2—N6	96.84 (9)	N3—C12—C11	122.0 (2)
N4—Cu2—N6	162.92 (9)	N3—C12—H12	119.0
N5—Cu2—O5	99.74 (8)	C11—C12—H12	119.0
N7—Cu2—O5	85.09 (8)	N4—C13—C14	122.3 (3)
N4—Cu2—O5	84.15 (8)	N4—C13—H13	118.9
N6—Cu2—O5	96.16 (8)	C14—C13—H13	118.9
O5—S1—O6	114.89 (13)	C15—C14—C13	119.1 (3)
O5—S1—O7	114.47 (13)	C15—C14—H14	120.5
O6—S1—O7	115.54 (13)	C13—C14—H14	120.5
O5—S1—C27	102.93 (14)	C14—C15—C16	119.3 (3)
O6—S1—C27	103.22 (15)	C14—C15—H15	120.3
O7—S1—C27	103.38 (15)	C16—C15—H15	120.3
O8—S2—O10	115.97 (15)	C17—C16—C15	118.3 (3)
O8—S2—O9	114.56 (14)	C17—C16—H16	120.9
O10—S2—O9	113.69 (13)	C15—C16—H16	120.9
O8—S2—C28	103.89 (13)	N4—C17—C16	122.8 (2)
O10—S2—C28	102.71 (13)	N4—C17—C18	115.7 (2)
O9—S2—C28	103.82 (13)	C16—C17—C18	121.5 (2)
C5—N1—C1	118.9 (2)	O3—C18—N5	127.5 (2)
C5—N1—Cu1	113.08 (17)	O3—C18—C17	121.2 (2)
C1—N1—Cu1	128.01 (18)	N5—C18—C17	111.3 (2)
C6—N2—C7	124.7 (2)	O4—C19—N5	128.4 (2)
C6—N2—Cu1	117.27 (17)	O4—C19—C20	118.8 (2)
C7—N2—Cu1	117.67 (17)	N5—C19—C20	112.7 (2)
C12—N3—C8	118.8 (2)	N6—C20—C21	123.2 (2)
C12—N3—Cu1	127.81 (18)	N6—C20—C19	115.0 (2)
C8—N3—Cu1	112.95 (17)	C21—C20—C19	121.8 (2)
C13—N4—C17	118.3 (2)	C20—C21—C22	118.1 (2)
C13—N4—Cu2	128.22 (19)	C20—C21—H21	120.9
C17—N4—Cu2	113.47 (17)	C22—C21—H21	120.9
C19—N5—C18	124.5 (2)	C23—C22—C21	118.8 (3)
C19—N5—Cu2	117.75 (17)	C23—C22—H22	120.6
C18—N5—Cu2	117.49 (17)	C21—C22—H22	120.6
C24—N6—C20	118.2 (2)	C22—C23—C24	119.7 (3)
C24—N6—Cu2	128.81 (19)	C22—C23—H23	120.2
C20—N6—Cu2	112.96 (17)	C24—C23—H23	120.2
C25—N7—Cu2	169.2 (2)	N6—C24—C23	122.0 (3)
C18—O3—Cu1	123.40 (17)	N6—C24—H24	119.0
C19—O4—Cu1	130.64 (17)	C23—C24—H24	119.0
S1—O5—Cu2	128.85 (12)	N7—C25—C26	178.2 (3)
N1—C1—C2	121.9 (3)	C25—C26—H26A	109.5
N1—C1—H1	119.0	C25—C26—H26B	109.5
C2—C1—H1	119.0	H26A—C26—H26B	109.5
C3—C2—C1	118.7 (3)	C25—C26—H26C	109.5
C3—C2—H2	120.6	H26A—C26—H26C	109.5
C1—C2—H2	120.6	H26B—C26—H26C	109.5
C2—C3—C4	119.8 (3)	F2—C27—F3	107.4 (3)
C2—C3—H3	120.1	F2—C27—F1	107.6 (3)
C4—C3—H3	120.1	F3—C27—F1	107.6 (3)
C3—C4—C5	118.5 (3)	F2—C27—S1	112.3 (2)
C3—C4—H4	120.7	F3—C27—S1	111.2 (2)
C5—C4—H4	120.7	F1—C27—S1	110.5 (2)
N1—C5—C4	122.2 (2)	F4—C28—F5	108.4 (2)
N1—C5—C6	116.2 (2)	F4—C28—F6	106.6 (2)
C4—C5—C6	121.6 (2)	F5—C28—F6	107.3 (2)
O1—C6—N2	128.9 (2)	F4—C28—S2	112.5 (2)
O1—C6—C5	121.0 (2)	F5—C28—S2	111.41 (19)
N2—C6—C5	110.1 (2)	F6—C28—S2	110.37 (19)
O2—C7—N2	129.0 (2)

N2—Cu1—N1—C5	−3.42 (18)	N1—C5—C6—N2	4.8 (3)
O4—Cu1—N1—C5	−164.09 (17)	C4—C5—C6—N2	−176.5 (2)
N3—Cu1—N1—C5	−7.1 (4)	C6—N2—C7—O2	−7.3 (4)
O3—Cu1—N1—C5	110.98 (17)	Cu1—N2—C7—O2	179.8 (2)
N2—Cu1—N1—C1	179.3 (2)	C6—N2—C7—C8	172.0 (2)
O4—Cu1—N1—C1	18.6 (2)	Cu1—N2—C7—C8	−0.9 (3)
N3—Cu1—N1—C1	175.6 (3)	C12—N3—C8—C9	1.4 (4)
O3—Cu1—N1—C1	−66.4 (2)	Cu1—N3—C8—C9	174.49 (19)
O4—Cu1—N2—C6	88.9 (3)	C12—N3—C8—C7	−177.1 (2)
N1—Cu1—N2—C6	6.56 (18)	Cu1—N3—C8—C7	−4.1 (3)
N3—Cu1—N2—C6	−174.4 (2)	O2—C7—C8—N3	−177.3 (2)
O3—Cu1—N2—C6	−90.82 (19)	N2—C7—C8—N3	3.3 (3)
O4—Cu1—N2—C7	−97.7 (3)	O2—C7—C8—C9	4.1 (4)
N1—Cu1—N2—C7	179.96 (19)	N2—C7—C8—C9	−175.3 (2)
N3—Cu1—N2—C7	−0.96 (18)	N3—C8—C9—C10	−1.0 (4)
O3—Cu1—N2—C7	82.58 (19)	C7—C8—C9—C10	177.4 (2)
N2—Cu1—N3—C12	175.1 (2)	C8—C9—C10—C11	−0.5 (4)
O4—Cu1—N3—C12	−24.5 (2)	C9—C10—C11—C12	1.7 (4)
N1—Cu1—N3—C12	178.7 (3)	C8—N3—C12—C11	−0.2 (4)
O3—Cu1—N3—C12	59.3 (2)	Cu1—N3—C12—C11	−172.1 (2)
N2—Cu1—N3—C8	2.79 (17)	C10—C11—C12—N3	−1.3 (4)
O4—Cu1—N3—C8	163.21 (17)	C17—N4—C13—C14	−1.4 (4)
N1—Cu1—N3—C8	6.4 (4)	Cu2—N4—C13—C14	−178.7 (2)
O3—Cu1—N3—C8	−113.00 (17)	N4—C13—C14—C15	0.3 (4)
N5—Cu2—N4—C13	−179.7 (2)	C13—C14—C15—C16	0.9 (4)
N7—Cu2—N4—C13	−4.4 (2)	C14—C15—C16—C17	−1.0 (4)
N6—Cu2—N4—C13	171.5 (3)	C13—N4—C17—C16	1.3 (4)
O5—Cu2—N4—C13	79.6 (2)	Cu2—N4—C17—C16	179.0 (2)
N5—Cu2—N4—C17	2.86 (18)	C13—N4—C17—C18	−177.8 (2)
N7—Cu2—N4—C17	178.15 (18)	Cu2—N4—C17—C18	−0.1 (3)
N6—Cu2—N4—C17	−6.0 (4)	C15—C16—C17—N4	−0.1 (4)
O5—Cu2—N4—C17	−97.92 (18)	C15—C16—C17—C18	178.9 (2)
N4—Cu2—N5—C19	−179.5 (2)	Cu1—O3—C18—N5	−10.9 (4)
N6—Cu2—N5—C19	−2.17 (19)	Cu1—O3—C18—C17	169.94 (17)
O5—Cu2—N5—C19	−97.01 (19)	C19—N5—C18—O3	1.1 (4)
N4—Cu2—N5—C18	−5.51 (19)	Cu2—N5—C18—O3	−172.5 (2)
N6—Cu2—N5—C18	171.9 (2)	C19—N5—C18—C17	−179.7 (2)
O5—Cu2—N5—C18	77.03 (19)	Cu2—N5—C18—C17	6.7 (3)
N5—Cu2—N6—C24	−179.7 (2)	N4—C17—C18—O3	175.1 (2)
N7—Cu2—N6—C24	5.0 (2)	C16—C17—C18—O3	−4.0 (4)
N4—Cu2—N6—C24	−170.9 (3)	N4—C17—C18—N5	−4.2 (3)
O5—Cu2—N6—C24	−80.8 (2)	C16—C17—C18—N5	176.7 (2)
N5—Cu2—N6—C20	2.40 (17)	Cu1—O4—C19—N5	−6.8 (4)
N7—Cu2—N6—C20	−172.86 (18)	Cu1—O4—C19—C20	174.63 (16)
N4—Cu2—N6—C20	11.3 (4)	C18—N5—C19—O4	9.3 (4)
O5—Cu2—N6—C20	101.37 (17)	Cu2—N5—C19—O4	−177.1 (2)
N4—Cu2—N7—C25	−158.9 (13)	C18—N5—C19—C20	−172.1 (2)
N6—Cu2—N7—C25	22.3 (13)	Cu2—N5—C19—C20	1.5 (3)
O5—Cu2—N7—C25	117.9 (13)	C24—N6—C20—C21	−0.1 (4)
N2—Cu1—O3—C18	−170.46 (19)	Cu2—N6—C20—C21	178.0 (2)
O4—Cu1—O3—C18	9.6 (2)	C24—N6—C20—C19	179.6 (2)
N1—Cu1—O3—C18	103.0 (2)	Cu2—N6—C20—C19	−2.3 (3)
N3—Cu1—O3—C18	−89.9 (2)	O4—C19—C20—N6	179.4 (2)
N2—Cu1—O4—C19	178.8 (2)	N5—C19—C20—N6	0.6 (3)
N1—Cu1—O4—C19	−100.9 (2)	O4—C19—C20—C21	−0.9 (4)
N3—Cu1—O4—C19	84.8 (2)	N5—C19—C20—C21	−179.7 (2)
O3—Cu1—O4—C19	−1.5 (2)	N6—C20—C21—C22	−0.1 (4)
O6—S1—O5—Cu2	130.69 (15)	C19—C20—C21—C22	−179.8 (2)
O7—S1—O5—Cu2	−6.5 (2)	C20—C21—C22—C23	0.1 (4)
C27—S1—O5—Cu2	−117.89 (17)	C21—C22—C23—C24	0.0 (4)
N5—Cu2—O5—S1	22.78 (18)	C20—N6—C24—C23	0.2 (4)
N7—Cu2—O5—S1	−155.98 (17)	Cu2—N6—C24—C23	−177.5 (2)
N4—Cu2—O5—S1	103.22 (17)	C22—C23—C24—N6	−0.2 (4)
N6—Cu2—O5—S1	−59.61 (17)	O5—S1—C27—F2	−177.7 (2)
C5—N1—C1—C2	1.0 (4)	O6—S1—C27—F2	−57.9 (3)
Cu1—N1—C1—C2	178.2 (2)	O7—S1—C27—F2	62.9 (3)
N1—C1—C2—C3	−0.5 (4)	O5—S1—C27—F3	61.9 (3)
C1—C2—C3—C4	−0.2 (4)	O6—S1—C27—F3	−178.2 (2)
C2—C3—C4—C5	0.2 (4)	O7—S1—C27—F3	−57.5 (3)
C1—N1—C5—C4	−0.9 (4)	O5—S1—C27—F1	−57.5 (3)
Cu1—N1—C5—C4	−178.5 (2)	O6—S1—C27—F1	62.3 (3)
C1—N1—C5—C6	177.7 (2)	O7—S1—C27—F1	−176.9 (2)
Cu1—N1—C5—C6	0.1 (3)	O8—S2—C28—F4	−47.3 (2)
C3—C4—C5—N1	0.3 (4)	O10—S2—C28—F4	−168.5 (2)
C3—C4—C5—C6	−178.3 (2)	O9—S2—C28—F4	72.8 (2)
C7—N2—C6—O1	−2.7 (4)	O8—S2—C28—F5	−169.3 (2)
Cu1—N2—C6—O1	170.2 (2)	O10—S2—C28—F5	69.5 (2)
C7—N2—C6—C5	179.3 (2)	O9—S2—C28—F5	−49.2 (2)
Cu1—N2—C6—C5	−7.8 (3)	O8—S2—C28—F6	71.6 (2)
N1—C5—C6—O1	−173.4 (2)	O10—S2—C28—F6	−49.6 (2)
C4—C5—C6—O1	5.3 (4)	O9—S2—C28—F6	−168.27 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O9ⁱ	0.95	2.57	3.448 (3)	154
C4—H4···O1ⁱⁱ	0.95	2.53	3.210 (4)	128
C10—H10···F5ⁱⁱⁱ	0.95	2.54	3.239 (3)	130
C21—H21···O1^iv	0.95	2.48	3.257 (3)	140
C21—H21···O2^iv	0.95	2.37	3.203 (3)	147
C22—H22···O10^v	0.95	2.48	3.400 (3)	163

Symmetry codes: (i) x+1, y−1, z; (ii) −x+2, −y, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₂H₈N₃O₂)₂(CF₃SO₃)₂(C₂H₃N)]
M_r	918.70
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.9726 (7), 10.0569 (8), 18.3689 (15)
α, β, γ (°)	82.573 (1), 83.802 (1), 82.222 (1)
V (Å³)	1621.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.55
Crystal size (mm)	0.32 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.638, 0.768
No. of measured, independent and observed [I > 2σ(I)] reflections	15254, 5686, 5292
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.087, 1.04
No. of reflections	5686
No. of parameters	497
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.50

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O9ⁱ	0.95	2.57	3.448 (3)	154
C4—H4···O1ⁱⁱ	0.95	2.53	3.210 (4)	128
C10—H10···F5ⁱⁱⁱ	0.95	2.54	3.239 (3)	130
C21—H21···O1^iv	0.95	2.48	3.257 (3)	140
C21—H21···O2^iv	0.95	2.37	3.203 (3)	147
C22—H22···O10^v	0.95	2.48	3.400 (3)	163

Symmetry codes: (i) x+1, y−1, z; (ii) −x+2, −y, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+2, −y+1, −z+1; (v) x+1, y, z.

Acknowledgements

This work was supported by the Universidad Autónoma de Sinaloa, México (DGIP.PROFAPI-2010–024).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Cangussu de Castro Gomes, D. C., Marilena Toma, L., Stumpf, H. O., Adams, H., Thomas, J. A., Lloret, F. & Julve, M. (2008). Polyhedron, 27, 559–573. Google Scholar
Chowdhury, H., Rahaman, S. H., Ghosh, R., Sarkar, S. K., Fun, H.-K. & Ghosh, B. K. (2007). J. Mol. Struct. 826, 170–176. Web of Science CSD CrossRef CAS Google Scholar
Folgado, J. V., Beltran-Porter, D., Burriel, R., Fuertes, A. & Miravitlles, C. (1988). J. Chem. Soc. Dalton Trans. pp. 3041–3045. CSD CrossRef Web of Science Google Scholar
Ha, K. (2010). Z. Kristallogr. New Cryst. Struct. 225, 789–790. CAS Google Scholar
Ha, K. (2011). Z. Kristallogr. New Cryst. Struct. 226, 55–56. CAS Google Scholar
Halder, D., Zangrando, E. & Kanti Paine, T. (2010). Polyhedron, 29, 434–440. Web of Science CSD CrossRef CAS Google Scholar
Kajiwara, T., Senbsui, R., Noguchi, T., Kamiyama, A. & Ito, T. (2002). Inorg. Chim. Acta, 337, 299–307. Web of Science CSD CrossRef CAS Google Scholar
Larter, M. L., Phillips, M., Ortega, F., Aguirre, G., Somanathan, R. & Walsh, P. J. (1998). Tetrahedron Lett. 39, 4785–4788. Web of Science CSD CrossRef CAS Google Scholar
Li, X.-F., Qiu, T.-B., Hu, L.-X. & Hu, C.-Y. (2011). Acta Cryst. E67, m1765–m1766. Web of Science CSD CrossRef IUCr Journals Google Scholar
Miguel, P. J. S., Roitzsch, M., Yin, L., Lax, P. M., Holland, L., Krizanovic, O., Lutterbeck, M., Shurmann, E., Fusch, E. C. & Lippert, B. (2009). Dalton Trans. pp. 10774–10786. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sugimoto, H., Takahira, T., Yoshimura, T., Shiro, M., Yamasaki, M., Miyake, H., Umakoshi, K. & Sasaki, Y. (2002). Inorg. Chim. Acta, 337, 203–211. Web of Science CSD CrossRef CAS Google Scholar
Wocadlo, S., Massa, W. & Folgado, J. V. (1993). Inorg. Chim. Acta, 207, 199–206. CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages m1280-m1281

https://doi.org/10.1107/S1600536812038330

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Two coordination modes of CuII in a binuclear complex with N-(pyridin-2-yl­carbon­yl)pyridine-2-carboxamidate ligands

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Two coordination modes of Cu^II in a binuclear complex with N-(pyridin-2-ylcarbonyl)pyridine-2-carboxamidate ligands