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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
CCDC reference: 180767
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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.
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).
Crystal data top
[CuCl(C5H5N)3] | Dx = 1.355 Mg m−3 |
Mr = 336.29 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Cmc21 | Cell parameters from 4339 reflections |
a = 14.349 (2) Å | θ = 4.2–25.1° |
b = 9.831 (2) Å | µ = 1.48 mm−1 |
c = 11.685 (2) Å | T = 173 K |
V = 1648.3 (5) Å3 | Needle, pale yellow |
Z = 4 | 0.24 × 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 tube | 1199 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
ω scans | θmax = 25.2°, θmin = 4.2° |
Absorption correction: empirical (using intensity measurements) (MULABS; Spek, 1990; Blessing, 1995) | h = −17→15 |
Tmin = 0.718, Tmax = 0.971 | k = −11→11 |
6254 measured reflections | l = −13→13 |
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)] = 0.048 | H-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 reflections | Δρmax = 0.36 e Å−3 |
103 parameters | Δρmin = −0.54 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.5000 | 0.57884 (9) | 0.61232 (7) | 0.0317 (2) | |
Cl1 | 0.5000 | 0.7106 (3) | 0.4374 (2) | 0.0337 (6) | |
N1 | 0.6199 (2) | 0.4684 (3) | 0.6048 (6) | 0.0334 (9) | |
C2 | 0.6437 (5) | 0.3805 (6) | 0.6859 (6) | 0.0473 (17) | |
H2 | 0.6034 | 0.3704 | 0.7499 | 0.057* | |
C3 | 0.7239 (5) | 0.3032 (8) | 0.6822 (7) | 0.066 (2) | |
H3 | 0.7381 | 0.2421 | 0.7427 | 0.080* | |
C4 | 0.7830 (5) | 0.3153 (7) | 0.5902 (10) | 0.068 (3) | |
H4 | 0.8376 | 0.2610 | 0.5849 | 0.081* | |
C5 | 0.7615 (5) | 0.4071 (8) | 0.5062 (7) | 0.056 (2) | |
H5 | 0.8022 | 0.4202 | 0.4431 | 0.067* | |
C6 | 0.6780 (4) | 0.4822 (6) | 0.5149 (5) | 0.0380 (15) | |
H6 | 0.6623 | 0.5442 | 0.4556 | 0.046* | |
N11 | 0.5000 | 0.7206 (8) | 0.7418 (6) | 0.0290 (19) | |
C12 | 0.5000 | 0.6851 (9) | 0.8522 (8) | 0.040 (2) | |
H12 | 0.5000 | 0.5911 | 0.8712 | 0.048* | |
C13 | 0.5000 | 0.7795 (8) | 0.9398 (9) | 0.043 (2) | |
H13 | 0.5000 | 0.7512 | 1.0175 | 0.052* | |
C14 | 0.5000 | 0.9190 (10) | 0.9109 (7) | 0.050 (2) | |
H14 | 0.5000 | 0.9860 | 0.9695 | 0.060* | |
C15 | 0.5000 | 0.9570 (8) | 0.8004 (9) | 0.053 (3) | |
H15 | 0.5000 | 1.0503 | 0.7792 | 0.064* | |
C16 | 0.5000 | 0.8536 (8) | 0.7173 (8) | 0.043 (2) | |
H16 | 0.5000 | 0.8796 | 0.6390 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0294 (5) | 0.0294 (4) | 0.0363 (5) | 0.000 | 0.000 | −0.0037 (7) |
Cl1 | 0.0415 (15) | 0.0273 (11) | 0.0324 (13) | 0.000 | 0.000 | 0.0023 (13) |
N1 | 0.032 (2) | 0.0317 (18) | 0.037 (2) | 0.0011 (14) | 0.007 (3) | 0.000 (3) |
C2 | 0.041 (4) | 0.050 (4) | 0.051 (4) | 0.010 (3) | 0.007 (3) | 0.006 (3) |
C3 | 0.055 (5) | 0.067 (5) | 0.077 (6) | 0.029 (4) | −0.008 (4) | 0.015 (4) |
C4 | 0.035 (3) | 0.062 (4) | 0.107 (9) | 0.019 (3) | 0.001 (6) | −0.006 (6) |
C5 | 0.030 (4) | 0.073 (5) | 0.065 (5) | 0.004 (4) | 0.016 (3) | −0.019 (5) |
C6 | 0.026 (3) | 0.043 (3) | 0.046 (4) | 0.001 (3) | 0.004 (3) | −0.007 (3) |
N11 | 0.028 (4) | 0.030 (4) | 0.028 (4) | 0.000 | 0.000 | 0.010 (3) |
C12 | 0.041 (5) | 0.035 (5) | 0.045 (6) | 0.000 | 0.000 | −0.004 (4) |
C13 | 0.061 (6) | 0.028 (4) | 0.041 (5) | 0.000 | 0.000 | 0.001 (4) |
C14 | 0.071 (6) | 0.039 (5) | 0.039 (6) | 0.000 | 0.000 | −0.004 (5) |
C15 | 0.081 (8) | 0.020 (6) | 0.059 (7) | 0.000 | 0.000 | −0.003 (4) |
C16 | 0.058 (6) | 0.029 (4) | 0.042 (6) | 0.000 | 0.000 | 0.004 (4) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.036 (3) | C5—H5 | 0.9500 |
Cu1—N1i | 2.036 (3) | C6—H6 | 0.9500 |
Cu1—N11 | 2.058 (8) | N11—C12 | 1.336 (11) |
Cu1—Cl1 | 2.420 (3) | N11—C16 | 1.338 (11) |
N1—C2 | 1.327 (8) | C12—C13 | 1.381 (12) |
N1—C6 | 1.348 (8) | C12—H12 | 0.9500 |
C2—C3 | 1.380 (8) | C13—C14 | 1.413 (12) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C4 | 1.374 (11) | C14—C15 | 1.343 (13) |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.368 (12) | C15—C16 | 1.406 (11) |
C4—H4 | 0.9500 | C15—H15 | 0.9500 |
C5—C6 | 1.411 (9) | C16—H16 | 0.9500 |
| | | |
N1—Cu1—N1i | 115.3 (2) | N1—C6—C5 | 121.9 (6) |
N1—Cu1—N11 | 113.14 (19) | N1—C6—H6 | 119.0 |
N1i—Cu1—N11 | 113.14 (19) | C5—C6—H6 | 119.0 |
N1—Cu1—Cl1 | 104.41 (19) | C12—N11—C16 | 117.5 (8) |
N1i—Cu1—Cl1 | 104.41 (19) | C12—N11—Cu1 | 122.2 (7) |
N11—Cu1—Cl1 | 105.0 (2) | C16—N11—Cu1 | 120.3 (5) |
C2—N1—C6 | 117.6 (5) | N11—C12—C13 | 122.6 (9) |
C2—N1—Cu1 | 122.2 (5) | N11—C12—H12 | 118.7 |
C6—N1—Cu1 | 120.2 (4) | C13—C12—H12 | 118.7 |
N1—C2—C3 | 123.4 (7) | C12—C13—C14 | 118.4 (9) |
N1—C2—H2 | 118.3 | C12—C13—H13 | 120.8 |
C3—C2—H2 | 118.3 | C14—C13—H13 | 120.8 |
C4—C3—C2 | 119.4 (7) | C15—C14—C13 | 120.0 (9) |
C4—C3—H3 | 120.3 | C15—C14—H14 | 120.0 |
C2—C3—H3 | 120.3 | C13—C14—H14 | 120.0 |
C5—C4—C3 | 118.6 (7) | C14—C15—C16 | 117.6 (8) |
C5—C4—H4 | 120.7 | C14—C15—H15 | 121.2 |
C3—C4—H4 | 120.7 | C16—C15—H15 | 121.2 |
C4—C5—C6 | 119.0 (7) | N11—C16—C15 | 123.9 (8) |
C4—C5—H5 | 120.5 | N11—C16—H16 | 118.0 |
C6—C5—H5 | 120.5 | C15—C16—H16 | 118.0 |
| | | |
N1i—Cu1—N1—C2 | −64.7 (7) | N1—Cu1—N11—C12 | −66.75 (18) |
N11—Cu1—N1—C2 | 67.8 (5) | N1i—Cu1—N11—C12 | 66.75 (18) |
Cl1—Cu1—N1—C2 | −178.6 (4) | Cl1—Cu1—N11—C12 | 180.000 (4) |
N1i—Cu1—N1—C6 | 114.8 (4) | N1—Cu1—N11—C16 | 113.25 (18) |
N11—Cu1—N1—C6 | −112.8 (5) | N1i—Cu1—N11—C16 | −113.25 (18) |
Cl1—Cu1—N1—C6 | 0.8 (4) | Cl1—Cu1—N11—C16 | 0.000 (3) |
C6—N1—C2—C3 | −0.4 (10) | C16—N11—C12—C13 | 0.000 (6) |
Cu1—N1—C2—C3 | 179.1 (6) | Cu1—N11—C12—C13 | 180.000 (4) |
N1—C2—C3—C4 | −0.5 (12) | N11—C12—C13—C14 | 0.000 (6) |
C2—C3—C4—C5 | 1.9 (12) | C12—C13—C14—C15 | 0.000 (6) |
C3—C4—C5—C6 | −2.4 (12) | C13—C14—C15—C16 | 0.000 (6) |
C2—N1—C6—C5 | −0.2 (9) | C12—N11—C16—C15 | 0.000 (5) |
Cu1—N1—C6—C5 | −179.7 (5) | Cu1—N11—C16—C15 | 180.000 (4) |
C4—C5—C6—N1 | 1.6 (10) | C14—C15—C16—N11 | 0.000 (6) |
Symmetry code: (i) −x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cl1 | 0.95 | 2.85 | 3.519 (6) | 128 |
C16—H16···Cl1 | 0.95 | 2.88 | 3.560 (10) | 129 |
C2—H2···Cl1ii | 0.95 | 2.76 | 3.699 (7) | 169 |
Symmetry code: (ii) −x+1, −y+1, z+1/2. |
Comparative table of geometric parameters (Å, °). topStructure | Cu—Cl | Cu—N | Angles between |
| | | aromatic rings |
Title compound | 2.420 (3) | 2.036 (3) | 60.3 (2) |
| | 2.058 (8) | 59.4 (2) |
CETJUG | 2.458 (2) | 2.021 (5) | 62.7 |
CETJUG01 | 2.451 (4) | 2.029 (10) | 63.0 |
DUSMUZ | 2.412 (9) | 2.08 (1) | 60.0 |
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