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The Cu atom, the Cl atom and one of the pyridyl rings of the title compound, [CuCl(C5H5N)3], are located on a crystallographic mirror plane. As a result, there is a half mol­ecule in the asymmetric unit. Geometric parameters do not show unusual values.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001630/na6134sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001630/na6134Isup2.hkl
Contains datablock I

CCDC reference: 180767

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.048
  • wR factor = 0.075
  • Data-to-parameter ratio = 14.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.24 From the CIF: _reflns_number_total 1518 Count of symmetry unique reflns 825 Completeness (_total/calc) 184.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 693 Fraction of Friedel pairs measured 0.840 Are heavy atom types Z>Si present yes 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.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

(I) top
Crystal data top
[CuCl(C5H5N)3]Dx = 1.355 Mg m3
Mr = 336.29Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmc21Cell parameters from 4339 reflections
a = 14.349 (2) Åθ = 4.2–25.1°
b = 9.831 (2) ŵ = 1.48 mm1
c = 11.685 (2) ÅT = 173 K
V = 1648.3 (5) Å3Needle, pale yellow
Z = 40.24 × 0.04 × 0.02 mm
F(000) = 688
Data collection top
Stoe IPDS II two-circle
diffractometer
1518 independent reflections
Radiation source: fine-focus sealed tube1199 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ω scansθmax = 25.2°, θmin = 4.2°
Absorption correction: empirical (using intensity measurements)
(MULABS; Spek, 1990; Blessing, 1995)
h = 1715
Tmin = 0.718, Tmax = 0.971k = 1111
6254 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0115P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
1518 reflectionsΔρmax = 0.36 e Å3
103 parametersΔρmin = 0.54 e Å3
1 restraintAbsolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (4)
Special details top

Experimental. ;

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
Cu10.50000.57884 (9)0.61232 (7)0.0317 (2)
Cl10.50000.7106 (3)0.4374 (2)0.0337 (6)
N10.6199 (2)0.4684 (3)0.6048 (6)0.0334 (9)
C20.6437 (5)0.3805 (6)0.6859 (6)0.0473 (17)
H20.60340.37040.74990.057*
C30.7239 (5)0.3032 (8)0.6822 (7)0.066 (2)
H30.73810.24210.74270.080*
C40.7830 (5)0.3153 (7)0.5902 (10)0.068 (3)
H40.83760.26100.58490.081*
C50.7615 (5)0.4071 (8)0.5062 (7)0.056 (2)
H50.80220.42020.44310.067*
C60.6780 (4)0.4822 (6)0.5149 (5)0.0380 (15)
H60.66230.54420.45560.046*
N110.50000.7206 (8)0.7418 (6)0.0290 (19)
C120.50000.6851 (9)0.8522 (8)0.040 (2)
H120.50000.59110.87120.048*
C130.50000.7795 (8)0.9398 (9)0.043 (2)
H130.50000.75121.01750.052*
C140.50000.9190 (10)0.9109 (7)0.050 (2)
H140.50000.98600.96950.060*
C150.50000.9570 (8)0.8004 (9)0.053 (3)
H150.50001.05030.77920.064*
C160.50000.8536 (8)0.7173 (8)0.043 (2)
H160.50000.87960.63900.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0294 (5)0.0294 (4)0.0363 (5)0.0000.0000.0037 (7)
Cl10.0415 (15)0.0273 (11)0.0324 (13)0.0000.0000.0023 (13)
N10.032 (2)0.0317 (18)0.037 (2)0.0011 (14)0.007 (3)0.000 (3)
C20.041 (4)0.050 (4)0.051 (4)0.010 (3)0.007 (3)0.006 (3)
C30.055 (5)0.067 (5)0.077 (6)0.029 (4)0.008 (4)0.015 (4)
C40.035 (3)0.062 (4)0.107 (9)0.019 (3)0.001 (6)0.006 (6)
C50.030 (4)0.073 (5)0.065 (5)0.004 (4)0.016 (3)0.019 (5)
C60.026 (3)0.043 (3)0.046 (4)0.001 (3)0.004 (3)0.007 (3)
N110.028 (4)0.030 (4)0.028 (4)0.0000.0000.010 (3)
C120.041 (5)0.035 (5)0.045 (6)0.0000.0000.004 (4)
C130.061 (6)0.028 (4)0.041 (5)0.0000.0000.001 (4)
C140.071 (6)0.039 (5)0.039 (6)0.0000.0000.004 (5)
C150.081 (8)0.020 (6)0.059 (7)0.0000.0000.003 (4)
C160.058 (6)0.029 (4)0.042 (6)0.0000.0000.004 (4)
Geometric parameters (Å, º) top
Cu1—N12.036 (3)C5—H50.9500
Cu1—N1i2.036 (3)C6—H60.9500
Cu1—N112.058 (8)N11—C121.336 (11)
Cu1—Cl12.420 (3)N11—C161.338 (11)
N1—C21.327 (8)C12—C131.381 (12)
N1—C61.348 (8)C12—H120.9500
C2—C31.380 (8)C13—C141.413 (12)
C2—H20.9500C13—H130.9500
C3—C41.374 (11)C14—C151.343 (13)
C3—H30.9500C14—H140.9500
C4—C51.368 (12)C15—C161.406 (11)
C4—H40.9500C15—H150.9500
C5—C61.411 (9)C16—H160.9500
N1—Cu1—N1i115.3 (2)N1—C6—C5121.9 (6)
N1—Cu1—N11113.14 (19)N1—C6—H6119.0
N1i—Cu1—N11113.14 (19)C5—C6—H6119.0
N1—Cu1—Cl1104.41 (19)C12—N11—C16117.5 (8)
N1i—Cu1—Cl1104.41 (19)C12—N11—Cu1122.2 (7)
N11—Cu1—Cl1105.0 (2)C16—N11—Cu1120.3 (5)
C2—N1—C6117.6 (5)N11—C12—C13122.6 (9)
C2—N1—Cu1122.2 (5)N11—C12—H12118.7
C6—N1—Cu1120.2 (4)C13—C12—H12118.7
N1—C2—C3123.4 (7)C12—C13—C14118.4 (9)
N1—C2—H2118.3C12—C13—H13120.8
C3—C2—H2118.3C14—C13—H13120.8
C4—C3—C2119.4 (7)C15—C14—C13120.0 (9)
C4—C3—H3120.3C15—C14—H14120.0
C2—C3—H3120.3C13—C14—H14120.0
C5—C4—C3118.6 (7)C14—C15—C16117.6 (8)
C5—C4—H4120.7C14—C15—H15121.2
C3—C4—H4120.7C16—C15—H15121.2
C4—C5—C6119.0 (7)N11—C16—C15123.9 (8)
C4—C5—H5120.5N11—C16—H16118.0
C6—C5—H5120.5C15—C16—H16118.0
N1i—Cu1—N1—C264.7 (7)N1—Cu1—N11—C1266.75 (18)
N11—Cu1—N1—C267.8 (5)N1i—Cu1—N11—C1266.75 (18)
Cl1—Cu1—N1—C2178.6 (4)Cl1—Cu1—N11—C12180.000 (4)
N1i—Cu1—N1—C6114.8 (4)N1—Cu1—N11—C16113.25 (18)
N11—Cu1—N1—C6112.8 (5)N1i—Cu1—N11—C16113.25 (18)
Cl1—Cu1—N1—C60.8 (4)Cl1—Cu1—N11—C160.000 (3)
C6—N1—C2—C30.4 (10)C16—N11—C12—C130.000 (6)
Cu1—N1—C2—C3179.1 (6)Cu1—N11—C12—C13180.000 (4)
N1—C2—C3—C40.5 (12)N11—C12—C13—C140.000 (6)
C2—C3—C4—C51.9 (12)C12—C13—C14—C150.000 (6)
C3—C4—C5—C62.4 (12)C13—C14—C15—C160.000 (6)
C2—N1—C6—C50.2 (9)C12—N11—C16—C150.000 (5)
Cu1—N1—C6—C5179.7 (5)Cu1—N11—C16—C15180.000 (4)
C4—C5—C6—N11.6 (10)C14—C15—C16—N110.000 (6)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Cl10.952.853.519 (6)128
C16—H16···Cl10.952.883.560 (10)129
C2—H2···Cl1ii0.952.763.699 (7)169
Symmetry code: (ii) x+1, y+1, z+1/2.
Comparative table of geometric parameters (Å, °). top
StructureCu—ClCu—NAngles between
aromatic rings
Title compound2.420 (3)2.036 (3)60.3 (2)
2.058 (8)59.4 (2)
CETJUG2.458 (2)2.021 (5)62.7
CETJUG012.451 (4)2.029 (10)63.0
DUSMUZ2.412 (9)2.08 (1)60.0
 

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