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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012232/hk2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012232/hk2021Isup2.hkl
Contains datablock I

CCDC reference: 608351

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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

Computing details top

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 = 525.5Dx = 1.634 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 18086 reflections
a = 14.9595 (8) Åθ = 3.2–26.4°
b = 10.6537 (5) ŵ = 1.18 mm1
c = 14.7190 (8) ÅT = 120 K
β = 114.481 (5)°Needle, green
V = 2134.9 (2) Å30.60 × 0.15 × 0.13 mm
Z = 4
Data collection top
Oxford Model? CCD area-detector
diffractometer
2179 independent reflections
Graphite monochromator1844 reflections with I > 3σ(I)
Detector resolution: 8.3438 pixels mm-1Rint = 0.025
ω scansθmax = 26.4°, θmin = 3.2°
Absorption correction: numerical
(Crysalis RED; Oxford Diffraction, 2004)
h = 1818
Tmin = 0.745, Tmax = 0.863k = 1313
18086 measured reflectionsl = 1818
Refinement top
Refinement on F232 constraints
R[F > 3σ(F)] = 0.025H-atom parameters constrained
wR(F) = 0.071Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.25(Δ/σ)max = 0.007
2179 reflectionsΔρmax = 0.25 e Å3
160 parametersΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
Cu10.50.77088 (3)0.250.01304 (12)
Cl10.50.54677 (5)0.250.0143 (2)
N10.56169 (13)0.80727 (18)0.91243 (13)0.0278 (7)
N30.50.9164 (2)0.750.0421 (12)
N100.62372 (11)0.77870 (13)0.22962 (11)0.0128 (5)
N200.59240 (11)0.84886 (13)0.38841 (11)0.0130 (5)
C10.53232 (14)0.85341 (18)0.83487 (15)0.0218 (7)
C110.70049 (13)0.83397 (15)0.30659 (13)0.0128 (6)
C120.63943 (13)0.73385 (16)0.15291 (14)0.0156 (7)
C130.73030 (13)0.74502 (16)0.14679 (14)0.0167 (7)
C140.80671 (13)0.80351 (17)0.22230 (14)0.0170 (7)
C150.79386 (13)0.84887 (16)0.30630 (13)0.0141 (6)
C160.87112 (13)0.90358 (17)0.39203 (14)0.0182 (7)
C210.68385 (12)0.87023 (16)0.39221 (13)0.0126 (6)
C220.57721 (13)0.87814 (16)0.46904 (13)0.0163 (7)
C230.65121 (13)0.92588 (17)0.55679 (13)0.0176 (7)
C240.74359 (13)0.94604 (16)0.56134 (13)0.0177 (7)
C250.76186 (13)0.91947 (16)0.47652 (13)0.0151 (6)
C260.85585 (13)0.93701 (16)0.47337 (14)0.0185 (7)
H120.5845970.6929850.1014080.0187*
H130.7402140.712570.0908110.0201*
H140.8679740.8125190.2164880.0204*
H160.9356010.9184030.3950850.0219*
H220.5118140.8645910.4638250.0196*
H230.6385420.9448870.6141240.0211*
H240.7939130.9777830.6220240.0213*
H260.9109210.972680.5280660.0222*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.00955 (17)0.01807 (18)0.01223 (18)00.00525 (13)0
Cl10.0126 (3)0.0152 (3)0.0148 (3)00.0053 (2)0
N10.0277 (10)0.0394 (10)0.0184 (9)0.0014 (8)0.0116 (8)0.0039 (8)
N30.063 (2)0.0221 (13)0.0210 (14)00.0030 (14)0
N100.0116 (7)0.0134 (7)0.0125 (7)0.0006 (6)0.0042 (6)0.0010 (6)
N200.0134 (7)0.0122 (7)0.0127 (8)0.0007 (6)0.0048 (6)0.0025 (6)
C10.0196 (10)0.0219 (10)0.0232 (11)0.0020 (8)0.0081 (9)0.0105 (8)
C110.0128 (9)0.0103 (8)0.0143 (9)0.0012 (7)0.0046 (7)0.0037 (7)
C120.0166 (9)0.0146 (9)0.0162 (9)0.0006 (7)0.0076 (8)0.0002 (7)
C130.0191 (10)0.0176 (9)0.0170 (9)0.0026 (7)0.0111 (8)0.0016 (7)
C140.0144 (9)0.0170 (9)0.0234 (10)0.0020 (7)0.0116 (8)0.0052 (7)
C150.0122 (9)0.0124 (8)0.0170 (9)0.0006 (7)0.0053 (7)0.0043 (7)
C160.0113 (9)0.0177 (9)0.0237 (10)0.0016 (7)0.0054 (8)0.0043 (8)
C210.0116 (9)0.0116 (8)0.0135 (9)0.0015 (6)0.0040 (7)0.0035 (7)
C220.0169 (10)0.0165 (9)0.0170 (10)0.0019 (7)0.0085 (8)0.0012 (7)
C230.0232 (10)0.0165 (9)0.0136 (9)0.0034 (8)0.0081 (8)0.0000 (7)
C240.0196 (9)0.0144 (9)0.0136 (9)0.0016 (7)0.0013 (8)0.0001 (7)
C250.0152 (9)0.0119 (8)0.0158 (9)0.0013 (7)0.0040 (7)0.0031 (7)
C260.0130 (9)0.0175 (9)0.0186 (10)0.0024 (7)0.0003 (8)0.0010 (7)
Geometric parameters (Å, º) top
Cu1—Cl12.3876 (6)C13—C141.370 (2)
Cu1—N101.9956 (18)C13—H130.960
Cu1—N10i1.9956 (18)C14—C151.413 (3)
Cu1—N202.1018 (13)C14—H140.960
Cu1—N20i2.1018 (13)C15—C161.435 (2)
N1—C11.150 (3)C16—C261.356 (3)
N3—C11.321 (2)C16—H160.960
N3—C1ii1.321 (2)C22—H220.960
N10—C121.334 (3)C23—C241.372 (3)
N10—C111.3677 (19)C23—C221.403 (2)
N20—C221.334 (3)C23—H230.960
N20—C211.365 (3)C24—C251.413 (3)
C11—C151.408 (3)C24—H240.960
C11—C211.435 (3)C25—C211.406 (2)
C12—C131.404 (3)C26—C251.438 (3)
C12—H120.960C26—H260.960
Cl1—Cu1—N1092.39 (4)C14—C13—H13119.1
Cl1—Cu1—N10i92.39 (4)C13—C14—C15119.7 (2)
Cl1—Cu1—N20113.28 (4)C13—C14—H14118.7
Cl1—Cu1—N20i113.28 (4)C15—C14—H14121.7
N10—Cu1—N10i175.22 (6)C14—C15—C11117.33 (15)
N10—Cu1—N2081.42 (6)C14—C15—C16123.81 (19)
N10—Cu1—N20i96.67 (6)C11—C15—C16118.80 (19)
N10i—Cu1—N10175.22 (6)C15—C16—C26120.94 (19)
N10i—Cu1—N2096.67 (6)C15—C16—H16122.4
N10i—Cu1—N20i81.42 (6)C26—C16—H16116.7
N20—Cu1—N20i133.44 (5)N20—C21—C11117.05 (14)
N20i—Cu1—N20133.44 (5)N20—C21—C25123.33 (19)
C1—N3—C1ii118.9 (2)C11—C21—C25119.54 (18)
C1ii—N3—C1118.9 (2)N20—C22—C23122.92 (19)
Cu1—N10—C12127.74 (11)N20—C22—H22115.9
Cu1—N10—C11113.97 (14)C23—C22—H22121.2
C12—N10—C11118.26 (17)C24—C23—C22119.7 (2)
Cu1—N20—C22131.95 (13)C24—C23—H23119.1
Cu1—N20—C21110.55 (13)C22—C23—H23121.2
C22—N20—C21117.50 (14)C23—C24—C25119.02 (15)
N3—C1—N1174.8 (2)C23—C24—H24119.1
N10—C11—C15122.67 (19)C25—C24—H24121.9
N10—C11—C21116.84 (18)C26—C25—C24123.52 (15)
C15—C11—C21120.38 (14)C26—C25—C21119.01 (19)
N10—C12—C13122.61 (15)C24—C25—C21117.45 (18)
N10—C12—H12116.0C16—C26—C25121.26 (15)
C13—C12—H12121.4C16—C26—H26116.4
C12—C13—C14119.4 (2)C25—C26—H26122.4
C12—C13—H13121.5
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···N1ii0.962.563.307 (3)135
Symmetry code: (ii) x+1, y, z+3/2.
 

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