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In the complex cation of the title compound, [CuCl(C12H8N2)2][N(CN)2], the Cu atom is five-coordinated, within a distorted trigonal bipyramid, by two 1,10-phenanthroline molecules and one Cl ligand. The Cl ligand is coordinated in the equatorial plane and lies, along with the Cu atom, on the twofold rotation axis. The axial Cu—N distances are substantially shorter than the equatorial Cu—N distances. A twofold rotation axis passes through the central N atom of the anion.
Supporting information
CCDC reference: 608351
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.024
- wR factor = 0.071
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 9.57 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N10 .. 5.51 su
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
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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: JANA2000 (Petříček & Dušek, 2000); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: JANA2000.
Chlorobis(1,10-phenanthroline-
κ2N,
N')copper(II) dicyanamide
top
Crystal data top
[CuCl(C12H8N2)2](C2N3) | F(000) = 1068 |
Mr = 525.5 | Dx = 1.634 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 18086 reflections |
a = 14.9595 (8) Å | θ = 3.2–26.4° |
b = 10.6537 (5) Å | µ = 1.18 mm−1 |
c = 14.7190 (8) Å | T = 120 K |
β = 114.481 (5)° | Needle, green |
V = 2134.9 (2) Å3 | 0.60 × 0.15 × 0.13 mm |
Z = 4 | |
Data collection top
Oxford Model? CCD area-detector diffractometer | 2179 independent reflections |
Graphite monochromator | 1844 reflections with I > 3σ(I) |
Detector resolution: 8.3438 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 26.4°, θmin = 3.2° |
Absorption correction: numerical (Crysalis RED; Oxford Diffraction, 2004) | h = −18→18 |
Tmin = 0.745, Tmax = 0.863 | k = −13→13 |
18086 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 32 constraints |
R[F > 3σ(F)] = 0.025 | H-atom parameters constrained |
wR(F) = 0.071 | Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2] |
S = 1.25 | (Δ/σ)max = 0.007 |
2179 reflections | Δρmax = 0.25 e Å−3 |
160 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | |
Special details top
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors are based on F, with F set to zero for negative
F2. The threshold expression of F2 > n*σ(F2) is
used only for calculating R-factors etc. and is not relevant to
the choice of reflections for refinement. The program used for refinement, Jana2000, uses the weighting scheme based on
the experimental expectations, see _refine_ls_weighting_details, that does not
force S to be one. Therefore the values of S are usually larger
then the ones from the SHELX program. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.5 | 0.77088 (3) | 0.25 | 0.01304 (12) | |
Cl1 | 0.5 | 0.54677 (5) | 0.25 | 0.0143 (2) | |
N1 | 0.56169 (13) | 0.80727 (18) | 0.91243 (13) | 0.0278 (7) | |
N3 | 0.5 | 0.9164 (2) | 0.75 | 0.0421 (12) | |
N10 | 0.62372 (11) | 0.77870 (13) | 0.22962 (11) | 0.0128 (5) | |
N20 | 0.59240 (11) | 0.84886 (13) | 0.38841 (11) | 0.0130 (5) | |
C1 | 0.53232 (14) | 0.85341 (18) | 0.83487 (15) | 0.0218 (7) | |
C11 | 0.70049 (13) | 0.83397 (15) | 0.30659 (13) | 0.0128 (6) | |
C12 | 0.63943 (13) | 0.73385 (16) | 0.15291 (14) | 0.0156 (7) | |
C13 | 0.73030 (13) | 0.74502 (16) | 0.14679 (14) | 0.0167 (7) | |
C14 | 0.80671 (13) | 0.80351 (17) | 0.22230 (14) | 0.0170 (7) | |
C15 | 0.79386 (13) | 0.84887 (16) | 0.30630 (13) | 0.0141 (6) | |
C16 | 0.87112 (13) | 0.90358 (17) | 0.39203 (14) | 0.0182 (7) | |
C21 | 0.68385 (12) | 0.87023 (16) | 0.39221 (13) | 0.0126 (6) | |
C22 | 0.57721 (13) | 0.87814 (16) | 0.46904 (13) | 0.0163 (7) | |
C23 | 0.65121 (13) | 0.92588 (17) | 0.55679 (13) | 0.0176 (7) | |
C24 | 0.74359 (13) | 0.94604 (16) | 0.56134 (13) | 0.0177 (7) | |
C25 | 0.76186 (13) | 0.91947 (16) | 0.47652 (13) | 0.0151 (6) | |
C26 | 0.85585 (13) | 0.93701 (16) | 0.47337 (14) | 0.0185 (7) | |
H12 | 0.584597 | 0.692985 | 0.101408 | 0.0187* | |
H13 | 0.740214 | 0.71257 | 0.090811 | 0.0201* | |
H14 | 0.867974 | 0.812519 | 0.216488 | 0.0204* | |
H16 | 0.935601 | 0.918403 | 0.395085 | 0.0219* | |
H22 | 0.511814 | 0.864591 | 0.463825 | 0.0196* | |
H23 | 0.638542 | 0.944887 | 0.614124 | 0.0211* | |
H24 | 0.793913 | 0.977783 | 0.622024 | 0.0213* | |
H26 | 0.910921 | 0.97268 | 0.528066 | 0.0222* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.00955 (17) | 0.01807 (18) | 0.01223 (18) | 0 | 0.00525 (13) | 0 |
Cl1 | 0.0126 (3) | 0.0152 (3) | 0.0148 (3) | 0 | 0.0053 (2) | 0 |
N1 | 0.0277 (10) | 0.0394 (10) | 0.0184 (9) | −0.0014 (8) | 0.0116 (8) | −0.0039 (8) |
N3 | 0.063 (2) | 0.0221 (13) | 0.0210 (14) | 0 | −0.0030 (14) | 0 |
N10 | 0.0116 (7) | 0.0134 (7) | 0.0125 (7) | 0.0006 (6) | 0.0042 (6) | 0.0010 (6) |
N20 | 0.0134 (7) | 0.0122 (7) | 0.0127 (8) | 0.0007 (6) | 0.0048 (6) | 0.0025 (6) |
C1 | 0.0196 (10) | 0.0219 (10) | 0.0232 (11) | −0.0020 (8) | 0.0081 (9) | −0.0105 (8) |
C11 | 0.0128 (9) | 0.0103 (8) | 0.0143 (9) | 0.0012 (7) | 0.0046 (7) | 0.0037 (7) |
C12 | 0.0166 (9) | 0.0146 (9) | 0.0162 (9) | 0.0006 (7) | 0.0076 (8) | 0.0002 (7) |
C13 | 0.0191 (10) | 0.0176 (9) | 0.0170 (9) | 0.0026 (7) | 0.0111 (8) | 0.0016 (7) |
C14 | 0.0144 (9) | 0.0170 (9) | 0.0234 (10) | 0.0020 (7) | 0.0116 (8) | 0.0052 (7) |
C15 | 0.0122 (9) | 0.0124 (8) | 0.0170 (9) | 0.0006 (7) | 0.0053 (7) | 0.0043 (7) |
C16 | 0.0113 (9) | 0.0177 (9) | 0.0237 (10) | −0.0016 (7) | 0.0054 (8) | 0.0043 (8) |
C21 | 0.0116 (9) | 0.0116 (8) | 0.0135 (9) | 0.0015 (6) | 0.0040 (7) | 0.0035 (7) |
C22 | 0.0169 (10) | 0.0165 (9) | 0.0170 (10) | 0.0019 (7) | 0.0085 (8) | 0.0012 (7) |
C23 | 0.0232 (10) | 0.0165 (9) | 0.0136 (9) | 0.0034 (8) | 0.0081 (8) | 0.0000 (7) |
C24 | 0.0196 (9) | 0.0144 (9) | 0.0136 (9) | 0.0016 (7) | 0.0013 (8) | 0.0001 (7) |
C25 | 0.0152 (9) | 0.0119 (8) | 0.0158 (9) | 0.0013 (7) | 0.0040 (7) | 0.0031 (7) |
C26 | 0.0130 (9) | 0.0175 (9) | 0.0186 (10) | −0.0024 (7) | 0.0003 (8) | 0.0010 (7) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.3876 (6) | C13—C14 | 1.370 (2) |
Cu1—N10 | 1.9956 (18) | C13—H13 | 0.960 |
Cu1—N10i | 1.9956 (18) | C14—C15 | 1.413 (3) |
Cu1—N20 | 2.1018 (13) | C14—H14 | 0.960 |
Cu1—N20i | 2.1018 (13) | C15—C16 | 1.435 (2) |
N1—C1 | 1.150 (3) | C16—C26 | 1.356 (3) |
N3—C1 | 1.321 (2) | C16—H16 | 0.960 |
N3—C1ii | 1.321 (2) | C22—H22 | 0.960 |
N10—C12 | 1.334 (3) | C23—C24 | 1.372 (3) |
N10—C11 | 1.3677 (19) | C23—C22 | 1.403 (2) |
N20—C22 | 1.334 (3) | C23—H23 | 0.960 |
N20—C21 | 1.365 (3) | C24—C25 | 1.413 (3) |
C11—C15 | 1.408 (3) | C24—H24 | 0.960 |
C11—C21 | 1.435 (3) | C25—C21 | 1.406 (2) |
C12—C13 | 1.404 (3) | C26—C25 | 1.438 (3) |
C12—H12 | 0.960 | C26—H26 | 0.960 |
| | | |
Cl1—Cu1—N10 | 92.39 (4) | C14—C13—H13 | 119.1 |
Cl1—Cu1—N10i | 92.39 (4) | C13—C14—C15 | 119.7 (2) |
Cl1—Cu1—N20 | 113.28 (4) | C13—C14—H14 | 118.7 |
Cl1—Cu1—N20i | 113.28 (4) | C15—C14—H14 | 121.7 |
N10—Cu1—N10i | 175.22 (6) | C14—C15—C11 | 117.33 (15) |
N10—Cu1—N20 | 81.42 (6) | C14—C15—C16 | 123.81 (19) |
N10—Cu1—N20i | 96.67 (6) | C11—C15—C16 | 118.80 (19) |
N10i—Cu1—N10 | 175.22 (6) | C15—C16—C26 | 120.94 (19) |
N10i—Cu1—N20 | 96.67 (6) | C15—C16—H16 | 122.4 |
N10i—Cu1—N20i | 81.42 (6) | C26—C16—H16 | 116.7 |
N20—Cu1—N20i | 133.44 (5) | N20—C21—C11 | 117.05 (14) |
N20i—Cu1—N20 | 133.44 (5) | N20—C21—C25 | 123.33 (19) |
C1—N3—C1ii | 118.9 (2) | C11—C21—C25 | 119.54 (18) |
C1ii—N3—C1 | 118.9 (2) | N20—C22—C23 | 122.92 (19) |
Cu1—N10—C12 | 127.74 (11) | N20—C22—H22 | 115.9 |
Cu1—N10—C11 | 113.97 (14) | C23—C22—H22 | 121.2 |
C12—N10—C11 | 118.26 (17) | C24—C23—C22 | 119.7 (2) |
Cu1—N20—C22 | 131.95 (13) | C24—C23—H23 | 119.1 |
Cu1—N20—C21 | 110.55 (13) | C22—C23—H23 | 121.2 |
C22—N20—C21 | 117.50 (14) | C23—C24—C25 | 119.02 (15) |
N3—C1—N1 | 174.8 (2) | C23—C24—H24 | 119.1 |
N10—C11—C15 | 122.67 (19) | C25—C24—H24 | 121.9 |
N10—C11—C21 | 116.84 (18) | C26—C25—C24 | 123.52 (15) |
C15—C11—C21 | 120.38 (14) | C26—C25—C21 | 119.01 (19) |
N10—C12—C13 | 122.61 (15) | C24—C25—C21 | 117.45 (18) |
N10—C12—H12 | 116.0 | C16—C26—C25 | 121.26 (15) |
C13—C12—H12 | 121.4 | C16—C26—H26 | 116.4 |
C12—C13—C14 | 119.4 (2) | C25—C26—H26 | 122.4 |
C12—C13—H13 | 121.5 | | |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···N1ii | 0.96 | 2.56 | 3.307 (3) | 135 |
Symmetry code: (ii) −x+1, y, −z+3/2. |
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