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In the title compound, [CuCl2(C16H16N2O4)], which crystallizes in the monoclinic space group C2/c, mol­ecules are located on twofold rotation axes passing through the Cu centers and bisecting the bipyridyl ligands. They are interconnected by weak C—H...O and C—H...Cl interactions to form a two-dimensional network which stacks along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021257/ac6111sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021257/ac6111Isup2.hkl
Contains datablock I

CCDC reference: 252748

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.068
  • wR factor = 0.138
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Dichloro[3,3'-bis(ethoxycarbonyl)-2,2'-bipyridyl-κ2N,N']copper(II) top
Crystal data top
[CuCl2(C16H16N2O4)]F(000) = 884
Mr = 434.75Dx = 1.670 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.3605 (16) ÅCell parameters from 2620 reflections
b = 11.2772 (15) Åθ = 2.6–25.1°
c = 13.5039 (19) ŵ = 1.60 mm1
β = 91.269 (3)°T = 293 K
V = 1729.6 (4) Å3Needles, green
Z = 40.24 × 0.18 × 0.06 mm
Data collection top
Siemens SMART CCD
diffractometer
1523 independent reflections
Radiation source: fine-focus sealed tube1238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 25.1°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1013
Tmin = 0.673, Tmax = 0.909k = 1311
2620 measured reflectionsl = 1316
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.23 w = 1/[σ2(Fo2) + 18.8764P]
where P = (Fo2 + 2Fc2)/3
1523 reflections(Δ/σ)max < 0.001
115 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.48 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
Cu10.00000.10596 (10)0.75000.0336 (3)
Cl10.08595 (17)0.01667 (16)0.64340 (13)0.0494 (5)
O10.1304 (4)0.5643 (4)0.7927 (3)0.0439 (12)
N10.0203 (4)0.2421 (4)0.6560 (4)0.0305 (12)
C10.0585 (6)0.2256 (6)0.5649 (4)0.0362 (15)
H10.05280.14880.53630.043*
O20.1333 (4)0.6447 (4)0.6409 (3)0.0412 (11)
C20.1059 (6)0.3159 (6)0.5110 (5)0.0399 (16)
H20.12750.30380.44420.048*
C30.1216 (6)0.4252 (6)0.5559 (5)0.0378 (16)
H30.15830.48790.52100.045*
C40.0839 (6)0.4434 (5)0.6516 (4)0.0313 (14)
C50.0271 (5)0.3504 (5)0.6996 (4)0.0277 (13)
C60.1165 (5)0.5563 (6)0.7039 (5)0.0340 (15)
C70.1718 (8)0.7573 (6)0.6864 (6)0.059 (2)
H7A0.10620.79300.72310.071*
H7B0.23800.74270.73370.071*
C80.2094 (8)0.8389 (7)0.6081 (6)0.062 (2)
H8C0.28010.80750.57720.093*
H8A0.22690.91680.63710.093*
H8B0.14620.84690.55800.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0485 (7)0.0245 (6)0.0279 (6)0.0000.0021 (5)0.000
Cl10.0674 (13)0.0379 (10)0.0427 (10)0.0110 (9)0.0040 (9)0.0055 (8)
O10.061 (3)0.038 (3)0.034 (3)0.008 (2)0.002 (2)0.009 (2)
N10.038 (3)0.027 (3)0.026 (3)0.002 (2)0.003 (2)0.000 (2)
C10.048 (4)0.034 (3)0.027 (3)0.001 (3)0.005 (3)0.004 (3)
O20.053 (3)0.031 (2)0.040 (3)0.006 (2)0.000 (2)0.007 (2)
C20.048 (4)0.048 (4)0.024 (3)0.001 (3)0.007 (3)0.001 (3)
C30.047 (4)0.033 (4)0.034 (4)0.002 (3)0.004 (3)0.002 (3)
C40.038 (4)0.029 (3)0.027 (3)0.002 (3)0.000 (3)0.004 (3)
C50.033 (3)0.024 (3)0.026 (3)0.003 (3)0.003 (3)0.000 (3)
C60.032 (4)0.033 (3)0.038 (4)0.000 (3)0.004 (3)0.001 (3)
C70.083 (6)0.035 (4)0.059 (5)0.013 (4)0.002 (4)0.014 (4)
C80.075 (6)0.042 (5)0.069 (6)0.018 (4)0.003 (5)0.008 (4)
Geometric parameters (Å, º) top
Cu1—N1i2.009 (5)C2—H20.9500
Cu1—N12.009 (5)C3—C41.387 (8)
Cu1—Cl12.2082 (18)C3—H30.9500
Cu1—Cl1i2.2082 (18)C4—C51.398 (8)
O1—C61.209 (7)C4—C61.498 (9)
N1—C11.326 (7)C5—C5i1.506 (11)
N1—C51.357 (7)C7—C81.472 (10)
C1—C21.370 (9)C7—H7A0.9900
C1—H10.9500C7—H7B0.9900
O2—C61.327 (7)C8—H8C0.9800
O2—C71.473 (8)C8—H8A0.9800
C2—C31.383 (9)C8—H8B0.9800
N1i—Cu1—N180.3 (3)C3—C4—C6119.1 (6)
N1i—Cu1—Cl1146.67 (15)C5—C4—C6122.1 (5)
N1—Cu1—Cl197.01 (15)N1—C5—C4119.8 (5)
N1i—Cu1—Cl1i97.01 (15)N1—C5—C5i111.8 (3)
N1—Cu1—Cl1i146.67 (15)C4—C5—C5i128.4 (4)
Cl1—Cu1—Cl1i102.45 (10)O1—C6—O2124.2 (6)
C1—N1—C5120.8 (5)O1—C6—C4123.8 (6)
C1—N1—Cu1121.5 (4)O2—C6—C4112.0 (5)
C5—N1—Cu1114.8 (4)C8—C7—O2109.2 (6)
N1—C1—C2122.0 (6)C8—C7—H7A109.8
N1—C1—H1119.0O2—C7—H7A109.8
C2—C1—H1119.0C8—C7—H7B109.8
C6—O2—C7115.3 (5)O2—C7—H7B109.8
C1—C2—C3118.6 (6)H7A—C7—H7B108.3
C1—C2—H2120.7C7—C8—H8C109.5
C3—C2—H2120.7C7—C8—H8A109.5
C2—C3—C4120.0 (6)H8C—C8—H8A109.5
C2—C3—H3120.0C7—C8—H8B109.5
C4—C3—H3120.0H8C—C8—H8B109.5
C3—C4—C5118.5 (6)H8A—C8—H8B109.5
N1i—Cu1—N1—C1169.5 (6)C1—N1—C5—C5i177.0 (6)
Cl1—Cu1—N1—C144.1 (5)Cu1—N1—C5—C5i21.8 (8)
Cl1i—Cu1—N1—C181.5 (6)C3—C4—C5—N16.4 (9)
N1i—Cu1—N1—C58.4 (3)C6—C4—C5—N1166.9 (6)
Cl1—Cu1—N1—C5154.8 (4)C3—C4—C5—C5i176.5 (7)
Cl1i—Cu1—N1—C579.6 (5)C6—C4—C5—C5i10.2 (11)
C5—N1—C1—C20.1 (10)C7—O2—C6—O10.2 (9)
Cu1—N1—C1—C2160.1 (5)C7—O2—C6—C4176.9 (6)
N1—C1—C2—C34.6 (10)C3—C4—C6—O1150.0 (7)
C1—C2—C3—C43.5 (10)C5—C4—C6—O123.3 (10)
C2—C3—C4—C51.9 (10)C3—C4—C6—O227.2 (8)
C2—C3—C4—C6171.6 (6)C5—C4—C6—O2159.6 (6)
C1—N1—C5—C45.4 (9)C6—O2—C7—C8168.8 (6)
Cu1—N1—C5—C4155.8 (5)
Symmetry code: (i) x, y, z+3/2.
 

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