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The structures of five compounds consisting of (prop-2-en-1-yl)bis­[(pyridin-2-yl)methyl­idene]amine complexed with copper in both the CuI and CuII oxidation states are presented, namely chlorido­{(prop-2-en-1-yl)bis­[(pyridin-2-yl)methyl­idene]amine-[kappa]3N,N',N''}copper(I) 0.18-hydrate, [CuCl(C15H17N3)]·0.18H2O, (1), catena-poly[[copper(I)-[mu]2-(prop-2-en-1-yl)bis­[(pyridin-2-yl)methylidene]amine-[kappa]5N,N',N'':C2,C3] perchlorate aceto­nitrile monosolvate], {[Cu(C15H17N3)]ClO4·CH3CN}n, (2), di­chlorido­{(prop-2-en-1-yl)bis­[(pyridin-2-yl)methyl­idene]amine-[kappa]3N,N',N''}copper(II) di­chloro­methane monosolvate, [CuCl2(C15H17N3)]·CH2Cl2, (3), chlorido­{(prop-2-en-1-yl)bis­[(pyridin-2-yl)methyl­idene]amine-[kappa]3N,N',N''}copper(II) perchlorate, [CuCl(C15H17N3)]ClO4, (4), and di-[mu]-chlorido-bis­({(prop-2-en-1-yl)bis­[(pyridin-2-yl)methyl­idene]amine-[kappa]3N,N',N''}copper(II)) bis­(tetra­phenyl­borate), [Cu2Cl2(C15H17N3)2][(C6H5)4B]2, (5). Sys­tematic variation of the anion from a coordinating chloride to a noncoordinating perchlorate for two CuI complexes results in either a discrete mol­ecular species, as in (1), or a one-dimensional chain structure, as in (2). In complex (1), there are two crystallographically independent mol­ecules in the asymmetric unit. Complex (2) consists of the CuI atom coordinated by the amine and pyridyl N atoms of one ligand and by the vinyl moiety of another unit related by the crystallographic screw axis, yielding a one-dimensional chain parallel to the crystallographic b axis. Three complexes with CuII show that varying the anion composition from two chlorides, to a chloride and a perchlorate to a chloride and a tetra­phenylborate results in discrete mol­ecular species, as in (3) and (4), or a bridged bis-[mu]-chlorido complex, as in (5). Complex (3) shows two strongly bound Cl atoms, while complex (4) has one strongly bound Cl atom and a weaker coordination by one perchlorate O atom. The large noncoordinating tetra­phenyl­borate anion in complex (5) results in the core-bridged Cu2Cl2 moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615010335/sk3587sup1.cif
Contains datablocks 1, 2, 3, 4, 5, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35871sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35872sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35873sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35874sup5.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615010335/sk35875sup6.hkl
Contains datablock 5

CCDC references: 1403831; 1403830; 1403829; 1403828; 1403827

Computing details top

Data collection: SMART (Bruker, 2008) for (1); APEX2 (Bruker, 2008) for (2), (3), (4), (5). For all compounds, cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008) for (1); OLEX2 (Dolomanov et al., 2009) for (2), (3), (4), (5). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) for (1); publCIF (Westrip, 2010) for (2), (3), (4), (5).

(1) Chlorido{(prop-2-en-1-yl)bis[pyridin-2-yl)methylidene]amine-κ3N,N',N''}copper(I) 0.18-hydrate top
Crystal data top
[CuCl(C15H17N3)]·0.18H2ODx = 1.465 Mg m3
Mr = 341.52Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 9910 reflections
a = 29.2238 (13) Åθ = 2.5–27.6°
b = 8.2252 (4) ŵ = 1.58 mm1
c = 12.8789 (6) ÅT = 150 K
V = 3095.7 (2) Å3Rhomboid, orange
Z = 80.32 × 0.28 × 0.12 mm
F(000) = 1406
Data collection top
Bruker SMART APEXII
diffractometer
10665 independent reflections
Radiation source: fine-focus sealed tube8406 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.33 pixels mm-1θmax = 32.6°, θmin = 2.1°
φ and ω scansh = 4342
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1212
Tmin = 0.629, Tmax = 0.837l = 1818
37660 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0212P)2 + 0.6853P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.041
10665 reflectionsΔρmax = 0.41 e Å3
608 parametersΔρmin = 0.43 e Å3
139 restraintsAbsolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.504 (10)
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. Refined as a 2-component inversion twin. Twin component factor refined to 0.503:0.497. Inspection of the structure did not reveal a potential missed inversion center.

The ligands were found to be disordered on both copper complex molecules. The disorder was immediately apparent in the orientation of the methylene carbons within the ligand. The model was developed whereby the pyridyl rings were modeled from the geometry of the methylene carbon relative to the pyridyl ring. Inclusion of these atoms with occupancies summed independently to unity for the two molecules, yielded ratios of 0.76:0.34 and 0.57:0.43. These disordered atoms were treated with an anisotropic model. Atoms in the minor components in the molecules were restrained to have similar atomic displacement parameters.

Residual electron density was observed in a region located away from the main molecules. It was assumed to be a molecule of water from the crystallization solvent. This residual density was assumed to be solvent water of crystallization. An oxygen atom was included at this site and its occupancy refined independently, yielding an occpancy of 0.35. Hydrogen atoms on the water were included in idealized positions oriented towards nearby chlorine atoms and refined with a fixed O–H distance = 0.85 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.11243 (2)0.82677 (4)1.17764 (3)0.03331 (8)
Cl10.10667 (3)1.09481 (9)1.16052 (7)0.04425 (19)
N20.12430 (8)0.6390 (3)1.0519 (2)0.0325 (5)
N10.05572 (19)0.6797 (7)1.1938 (5)0.0323 (12)0.765 (4)
C10.0256 (2)0.6867 (9)1.2700 (6)0.0438 (14)0.765 (4)
H1A0.03100.76181.32480.053*0.765 (4)
C20.0134 (2)0.5906 (12)1.2749 (7)0.061 (2)0.765 (4)
H2A0.03490.60261.32980.073*0.765 (4)
C30.0200 (2)0.4786 (12)1.1985 (8)0.066 (2)0.765 (4)
H3A0.04590.40881.19990.079*0.765 (4)
C40.01060 (19)0.4679 (8)1.1209 (6)0.0557 (15)0.765 (4)
H4A0.00650.38951.06750.067*0.765 (4)
C50.04806 (15)0.5709 (6)1.1188 (4)0.0391 (11)0.765 (4)
C60.08007 (14)0.5699 (6)1.0274 (3)0.0441 (11)0.765 (4)
H6A0.08430.45651.00340.053*0.765 (4)
H6B0.06610.63240.96980.053*0.765 (4)
C70.15281 (12)0.5199 (4)1.1136 (4)0.0353 (8)0.765 (4)
H7A0.13280.45871.16180.042*0.765 (4)
H7B0.16730.44101.06570.042*0.765 (4)
C80.18899 (13)0.6066 (5)1.1739 (4)0.0320 (8)0.765 (4)
C90.23381 (18)0.5495 (7)1.1840 (5)0.0448 (14)0.765 (4)
H9A0.24290.45261.14950.054*0.765 (4)
C100.2647 (2)0.6335 (13)1.2440 (8)0.057 (4)0.765 (4)
H10A0.29530.59551.25120.069*0.765 (4)
C110.2511 (3)0.7705 (14)1.2923 (6)0.0460 (19)0.765 (4)
H11A0.27180.83211.33350.055*0.765 (4)
C120.2062 (2)0.8185 (11)1.2800 (5)0.038 (4)0.765 (4)
H12A0.19660.91391.31540.046*0.765 (4)
N30.1756 (2)0.7417 (7)1.2227 (4)0.0306 (12)0.765 (4)
C130.15056 (14)0.6874 (6)0.9602 (3)0.0379 (10)0.765 (4)
H13A0.15140.59710.90940.045*0.765 (4)
H13B0.18240.71380.98030.045*0.765 (4)
C1A0.0265 (7)0.7338 (18)1.2829 (13)0.031 (4)0.235 (4)
H1AA0.02970.82721.32570.037*0.235 (4)
C2A0.0137 (6)0.643 (2)1.2862 (16)0.050 (7)0.235 (4)
H2AA0.03780.67501.33120.060*0.235 (4)
C3A0.0184 (5)0.507 (2)1.2236 (17)0.051 (8)0.235 (4)
H3AA0.04590.44491.22590.061*0.235 (4)
C4A0.0169 (5)0.4605 (16)1.1578 (12)0.052 (6)0.235 (4)
H4AA0.01370.36711.11510.062*0.235 (4)
C5A0.0571 (4)0.5510 (17)1.1545 (9)0.031 (4)0.235 (4)
N1A0.0619 (5)0.6876 (18)1.2171 (11)0.026 (4)0.235 (4)
C6A0.0996 (4)0.5042 (14)1.0951 (11)0.036 (3)0.235 (4)
H6AA0.12030.44371.14220.043*0.235 (4)
H6AB0.09080.42991.03810.043*0.235 (4)
C7A0.1706 (5)0.6225 (17)1.0321 (11)0.039 (3)0.235 (4)
H7AA0.18060.70520.98100.047*0.235 (4)
H7AB0.17700.51351.00300.047*0.235 (4)
C8A0.1961 (4)0.6445 (15)1.1315 (9)0.030 (3)0.235 (4)
C9A0.2386 (4)0.5729 (19)1.1481 (12)0.039 (4)0.235 (4)
H9AA0.24960.49251.10150.046*0.235 (4)
C10A0.2650 (6)0.619 (3)1.2330 (17)0.043 (9)0.235 (4)
H10B0.29400.57031.24430.052*0.235 (4)
C11A0.2489 (9)0.737 (3)1.3012 (16)0.054 (11)0.235 (4)
H11B0.26690.76851.35920.065*0.235 (4)
C12A0.2064 (9)0.808 (3)1.2846 (13)0.052 (16)0.235 (4)
H12B0.19540.88891.33130.062*0.235 (4)
N3A0.1800 (6)0.7622 (18)1.1998 (11)0.023 (4)0.235 (4)
C13A0.0977 (4)0.6876 (16)0.9475 (10)0.035 (3)0.235 (4)
H13C0.09830.59850.89580.042*0.235 (4)
H13D0.06550.71880.96160.042*0.235 (4)
C140.12740 (15)0.8387 (5)0.9109 (3)0.0563 (10)
H14A0.11530.92040.95530.068*0.565 (4)
H14B0.14510.90560.95550.068*0.435 (4)
C150.12395 (14)0.8575 (6)0.8108 (3)0.0571 (11)
H15A0.13580.77710.76530.068*0.565 (4)
H15B0.10950.95170.78330.068*0.565 (4)
H15C0.10550.78540.77130.068*0.435 (4)
H15D0.13990.94340.77730.068*0.435 (4)
Cu20.13512 (2)0.25376 (4)0.61403 (4)0.03450 (8)
Cl20.13969 (3)0.34561 (11)0.77561 (6)0.04546 (19)
N50.13422 (8)0.3807 (3)0.4570 (2)0.0364 (6)
C200.0731 (3)0.1865 (11)0.4551 (9)0.0424 (19)0.565 (4)
N40.0783 (3)0.1566 (13)0.5539 (9)0.032 (2)0.565 (4)
C160.0438 (6)0.082 (2)0.5963 (14)0.054 (4)0.565 (4)
H16A0.04690.05850.66820.065*0.565 (4)
C170.0040 (5)0.032 (2)0.5521 (17)0.061 (4)0.565 (4)
H17A0.01960.01930.59060.074*0.565 (4)
C180.0004 (5)0.063 (3)0.4470 (18)0.070 (4)0.565 (4)
H18A0.02590.02840.40950.084*0.565 (4)
C190.0343 (4)0.1419 (17)0.3986 (10)0.058 (3)0.565 (4)
H19A0.03190.16730.32680.070*0.565 (4)
C20A0.0601 (3)0.2275 (13)0.4562 (10)0.039 (2)0.435 (4)
N4A0.0719 (4)0.1884 (15)0.5577 (10)0.030 (3)0.435 (4)
C16A0.0447 (5)0.082 (2)0.6147 (12)0.041 (5)0.435 (4)
H16B0.05280.05550.68410.050*0.435 (4)
C17A0.0057 (6)0.015 (3)0.5702 (17)0.078 (10)0.435 (4)
H17B0.01290.05720.60920.094*0.435 (4)
C18A0.0061 (4)0.054 (2)0.4687 (16)0.067 (8)0.435 (4)
H18B0.03280.00870.43830.080*0.435 (4)
C19A0.0211 (4)0.161 (2)0.4117 (11)0.065 (5)0.435 (4)
H19B0.01300.18730.34230.078*0.435 (4)
C210.1122 (2)0.2640 (8)0.3977 (4)0.0438 (15)0.565 (4)
H21A0.13450.17890.37760.053*0.565 (4)
H21B0.10050.31490.33330.053*0.565 (4)
C220.18080 (18)0.4193 (7)0.4282 (4)0.0374 (13)0.565 (4)
H22A0.18950.52590.45800.045*0.565 (4)
H22B0.18320.42690.35160.045*0.565 (4)
C230.21301 (19)0.2886 (8)0.4680 (4)0.0319 (12)0.565 (4)
C240.2554 (3)0.2653 (8)0.4216 (7)0.0379 (15)0.565 (4)
H24A0.26330.32560.36130.045*0.565 (4)
C250.2851 (7)0.159 (3)0.4609 (11)0.039 (3)0.565 (4)
H25A0.31380.14190.42840.047*0.565 (4)
C260.2734 (4)0.0749 (12)0.5499 (7)0.041 (2)0.565 (4)
H26A0.29470.00350.58190.050*0.565 (4)
C270.2306 (6)0.0954 (16)0.5912 (8)0.036 (2)0.565 (4)
H27A0.22190.03030.64890.044*0.565 (4)
N60.2000 (4)0.2050 (9)0.5533 (10)0.0279 (16)0.565 (4)
C280.10605 (18)0.5414 (7)0.4561 (4)0.0360 (13)0.565 (4)
H28A0.10600.58920.38560.043*0.565 (4)
H28B0.07400.51960.47670.043*0.565 (4)
C21A0.0879 (3)0.3661 (10)0.4135 (6)0.044 (2)0.435 (4)
H21C0.09050.35280.33740.053*0.435 (4)
H21D0.07130.46890.42670.053*0.435 (4)
C22A0.1637 (2)0.2446 (9)0.3957 (5)0.0344 (16)0.435 (4)
H22C0.14460.14710.38300.041*0.435 (4)
H22D0.17380.28800.32770.041*0.435 (4)
C23A0.2041 (2)0.2001 (10)0.4595 (6)0.0291 (14)0.435 (4)
C24A0.2485 (5)0.1974 (11)0.4206 (10)0.041 (2)0.435 (4)
H24B0.25440.22670.35060.050*0.435 (4)
C25A0.2853 (9)0.149 (3)0.4885 (13)0.039 (4)0.435 (4)
H25B0.31610.14870.46470.047*0.435 (4)
C26A0.2749 (5)0.1057 (16)0.5864 (9)0.040 (3)0.435 (4)
H26B0.29800.06710.63210.048*0.435 (4)
C27A0.2297 (7)0.118 (2)0.6193 (11)0.035 (3)0.435 (4)
H27B0.22310.09540.69010.042*0.435 (4)
N6A0.1950 (5)0.1595 (12)0.5572 (14)0.029 (2)0.435 (4)
C28A0.1560 (3)0.5289 (9)0.4437 (6)0.045 (2)0.435 (4)
H28C0.15270.56860.37150.054*0.435 (4)
H28D0.18890.52120.46100.054*0.435 (4)
C290.12750 (17)0.6542 (5)0.5301 (4)0.0672 (12)
H29A0.14210.61610.59130.081*0.565 (4)
H29B0.11380.61200.59130.081*0.435 (4)
C300.12567 (18)0.8041 (5)0.5087 (4)0.0743 (14)
H30A0.11090.83940.44700.089*0.565 (4)
H30B0.13910.88140.55430.089*0.565 (4)
H30C0.13960.84390.44710.089*0.435 (4)
H30D0.11030.87690.55420.089*0.435 (4)
O1W0.0746 (3)0.1987 (10)0.9325 (7)0.062 (3)0.356 (9)
H1WB0.08220.17360.99370.093*0.3558
H1WA0.09310.24140.88800.093*0.3558
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02953 (14)0.03819 (17)0.03223 (16)0.00511 (14)0.00027 (17)0.00228 (18)
Cl10.0450 (4)0.0343 (3)0.0534 (5)0.0043 (3)0.0062 (4)0.0054 (4)
N20.0295 (11)0.0363 (13)0.0317 (12)0.0055 (9)0.0041 (10)0.0035 (11)
N10.0218 (17)0.046 (3)0.029 (3)0.0018 (16)0.001 (2)0.0090 (18)
C10.036 (3)0.052 (4)0.043 (3)0.012 (3)0.010 (2)0.002 (3)
C20.027 (3)0.090 (6)0.065 (4)0.006 (3)0.023 (3)0.026 (5)
C30.034 (3)0.094 (5)0.068 (5)0.025 (3)0.000 (3)0.025 (4)
C40.038 (3)0.069 (3)0.060 (4)0.021 (2)0.005 (3)0.010 (3)
C50.026 (2)0.051 (3)0.041 (3)0.0032 (17)0.000 (2)0.009 (3)
C60.032 (2)0.060 (3)0.040 (2)0.0143 (19)0.0018 (17)0.007 (2)
C70.0337 (17)0.0312 (17)0.0410 (19)0.0013 (14)0.0073 (18)0.0037 (19)
C80.0295 (18)0.0336 (19)0.033 (2)0.0019 (14)0.005 (2)0.005 (2)
C90.038 (2)0.043 (3)0.054 (4)0.013 (2)0.010 (3)0.010 (3)
C100.023 (3)0.068 (6)0.081 (6)0.003 (3)0.010 (3)0.027 (4)
C110.030 (3)0.058 (4)0.050 (4)0.006 (3)0.014 (2)0.019 (3)
C120.031 (4)0.046 (5)0.037 (4)0.000 (2)0.012 (2)0.004 (3)
N30.028 (2)0.034 (2)0.030 (3)0.0005 (18)0.0010 (19)0.007 (2)
C130.0310 (19)0.051 (2)0.032 (2)0.0031 (18)0.0074 (16)0.0058 (18)
C1A0.029 (6)0.036 (7)0.028 (6)0.004 (5)0.011 (5)0.002 (5)
C2A0.045 (9)0.049 (9)0.055 (9)0.002 (6)0.003 (6)0.003 (6)
C3A0.048 (10)0.052 (9)0.053 (10)0.004 (6)0.004 (6)0.005 (6)
C4A0.052 (8)0.051 (7)0.053 (9)0.010 (5)0.008 (6)0.001 (6)
C5A0.029 (5)0.032 (5)0.032 (6)0.004 (4)0.003 (5)0.011 (5)
N1A0.024 (6)0.031 (6)0.022 (6)0.005 (4)0.008 (4)0.004 (4)
C6A0.042 (5)0.027 (4)0.040 (6)0.000 (4)0.002 (4)0.007 (4)
C7A0.037 (5)0.042 (5)0.039 (5)0.008 (4)0.006 (4)0.001 (5)
C8A0.023 (5)0.032 (5)0.034 (6)0.003 (4)0.001 (4)0.001 (5)
C9A0.030 (6)0.040 (6)0.046 (7)0.008 (5)0.002 (5)0.011 (5)
C10A0.036 (11)0.044 (10)0.049 (10)0.012 (6)0.007 (6)0.002 (6)
C11A0.050 (12)0.058 (13)0.053 (12)0.001 (6)0.004 (6)0.013 (6)
C12A0.054 (17)0.049 (17)0.052 (17)0.001 (7)0.003 (7)0.004 (7)
N3A0.022 (5)0.025 (5)0.022 (6)0.005 (4)0.002 (4)0.012 (4)
C13A0.033 (5)0.038 (5)0.034 (5)0.005 (4)0.004 (4)0.002 (4)
C140.075 (3)0.061 (2)0.0337 (18)0.016 (2)0.0046 (18)0.0005 (17)
C150.049 (2)0.088 (3)0.0350 (18)0.004 (2)0.0065 (15)0.0071 (19)
Cu20.03731 (16)0.03626 (16)0.02991 (14)0.00496 (16)0.00265 (17)0.00215 (16)
Cl20.0503 (5)0.0516 (5)0.0345 (4)0.0022 (4)0.0035 (3)0.0068 (4)
N50.0344 (13)0.0426 (15)0.0322 (13)0.0074 (11)0.0009 (11)0.0051 (11)
C200.035 (5)0.042 (5)0.051 (4)0.006 (3)0.010 (4)0.011 (4)
N40.031 (3)0.018 (4)0.049 (4)0.011 (3)0.010 (3)0.009 (3)
C160.047 (8)0.057 (10)0.059 (6)0.006 (6)0.001 (5)0.002 (5)
C170.020 (6)0.062 (8)0.102 (11)0.005 (5)0.002 (6)0.009 (8)
C180.038 (6)0.091 (11)0.081 (7)0.001 (6)0.005 (7)0.032 (7)
C190.035 (5)0.077 (7)0.062 (5)0.000 (5)0.006 (4)0.028 (5)
C20A0.031 (5)0.044 (6)0.041 (5)0.015 (4)0.010 (4)0.006 (4)
N4A0.029 (4)0.020 (5)0.042 (5)0.015 (3)0.002 (3)0.014 (3)
C16A0.017 (6)0.044 (9)0.063 (9)0.000 (6)0.016 (5)0.000 (6)
C17A0.038 (11)0.064 (11)0.13 (2)0.013 (8)0.016 (11)0.014 (11)
C18A0.024 (6)0.056 (10)0.12 (2)0.002 (5)0.008 (9)0.029 (11)
C19A0.029 (7)0.093 (10)0.072 (9)0.009 (7)0.008 (6)0.035 (8)
C210.047 (3)0.052 (4)0.033 (3)0.010 (3)0.005 (3)0.009 (3)
C220.037 (3)0.036 (3)0.039 (3)0.010 (2)0.010 (2)0.014 (2)
C230.030 (3)0.031 (3)0.035 (3)0.005 (2)0.004 (2)0.001 (2)
C240.034 (4)0.037 (3)0.043 (3)0.007 (3)0.010 (3)0.006 (3)
C250.038 (5)0.037 (4)0.041 (6)0.007 (3)0.010 (5)0.003 (5)
C260.039 (4)0.043 (4)0.043 (5)0.018 (3)0.000 (4)0.004 (4)
C270.042 (4)0.027 (4)0.041 (5)0.009 (3)0.004 (4)0.004 (4)
N60.027 (3)0.021 (4)0.036 (3)0.001 (3)0.001 (2)0.001 (4)
C280.035 (3)0.039 (3)0.034 (3)0.014 (2)0.004 (2)0.005 (2)
C21A0.041 (4)0.055 (5)0.036 (4)0.017 (4)0.007 (3)0.003 (3)
C22A0.041 (4)0.033 (3)0.029 (3)0.009 (3)0.001 (3)0.002 (3)
C23A0.031 (3)0.025 (3)0.031 (3)0.002 (3)0.003 (3)0.005 (3)
C24A0.043 (4)0.036 (4)0.045 (4)0.000 (4)0.010 (3)0.006 (4)
C25A0.030 (5)0.041 (6)0.046 (8)0.011 (4)0.001 (6)0.001 (6)
C26A0.035 (4)0.041 (5)0.045 (6)0.007 (3)0.003 (4)0.004 (4)
C27A0.032 (4)0.034 (5)0.040 (6)0.004 (4)0.001 (5)0.001 (4)
N6A0.031 (4)0.020 (5)0.036 (4)0.001 (4)0.003 (3)0.003 (4)
C28A0.059 (5)0.033 (4)0.044 (4)0.014 (4)0.010 (4)0.006 (3)
C290.104 (3)0.040 (2)0.058 (3)0.010 (2)0.010 (2)0.0094 (18)
C300.089 (3)0.052 (2)0.082 (3)0.022 (2)0.030 (3)0.009 (2)
O1W0.056 (5)0.059 (5)0.071 (6)0.003 (4)0.007 (4)0.019 (4)
Geometric parameters (Å, º) top
Cu1—N1A1.937 (12)Cu2—N6A2.050 (17)
Cu1—N32.058 (5)Cu2—N4A2.056 (10)
Cu1—N12.063 (5)Cu2—N62.090 (12)
Cu1—N3A2.066 (15)Cu2—Cl22.2178 (9)
Cu1—Cl12.2221 (8)Cu2—N52.276 (3)
Cu1—N22.265 (2)N5—C211.385 (7)
N2—C7A1.385 (13)N5—C28A1.385 (8)
N2—C6A1.435 (12)N5—C221.446 (6)
N2—C61.447 (4)N5—C21A1.469 (8)
N2—C131.463 (5)N5—C281.557 (6)
N2—C71.512 (5)N5—C22A1.619 (7)
N2—C13A1.605 (13)C20—N41.305 (10)
N1—C11.319 (6)C20—C191.397 (11)
N1—C51.336 (7)C20—C211.504 (12)
C1—C21.390 (9)N4—C161.301 (12)
C1—H1A0.9500C16—C171.358 (14)
C2—C31.361 (12)C16—H16A0.9500
C2—H2A0.9500C17—C181.380 (19)
C3—C41.343 (9)C17—H17A0.9500
C3—H3A0.9500C18—C191.339 (16)
C4—C51.385 (6)C18—H18A0.9500
C4—H4A0.9500C19—H19A0.9500
C5—C61.503 (7)C20A—N4A1.3900
C6—H6A0.9900C20A—C19A1.3900
C6—H6B0.9900C20A—C21A1.505 (14)
C7—C81.494 (6)N4A—C16A1.3900
C7—H7A0.9900C16A—C17A1.3900
C7—H7B0.9900C16A—H16B0.9500
C8—N31.334 (6)C17A—C18A1.3900
C8—C91.398 (6)C17A—H17B0.9500
C9—C101.375 (9)C18A—C19A1.3900
C9—H9A0.9500C18A—H18B0.9500
C10—C111.347 (10)C19A—H19B0.9500
C10—H10A0.9500C21—H21A0.9900
C11—C121.380 (6)C21—H21B0.9900
C11—H11A0.9500C22—C231.519 (7)
C12—N31.321 (6)C22—H22A0.9900
C12—H12A0.9500C22—H22B0.9900
C13—C141.552 (6)C23—N61.351 (13)
C13—H13A0.9900C23—C241.390 (9)
C13—H13B0.9900C24—C251.33 (2)
C1A—C2A1.3900C24—H24A0.9500
C1A—N1A1.3900C25—C261.383 (17)
C1A—H1AA0.9500C25—H25A0.9500
C2A—C3A1.3900C26—C271.368 (18)
C2A—H2AA0.9500C26—H26A0.9500
C3A—C4A1.3900C27—N61.361 (18)
C3A—H3AA0.9500C27—H27A0.9500
C4A—C5A1.3900C28—C291.470 (7)
C4A—H4AA0.9500C28—H28A0.9900
C5A—N1A1.3900C28—H28B0.9900
C5A—C6A1.509 (17)C21A—H21C0.9900
C6A—H6AA0.9900C21A—H21D0.9900
C6A—H6AB0.9900C22A—C23A1.486 (10)
C7A—C8A1.492 (18)C22A—H22C0.9900
C7A—H7AA0.9900C22A—H22D0.9900
C7A—H7AB0.9900C23A—N6A1.329 (19)
C8A—C9A1.3900C23A—C24A1.389 (15)
C8A—N3A1.3900C24A—C25A1.44 (3)
C9A—C10A1.3900C24A—H24B0.9500
C9A—H9AA0.9500C25A—C26A1.35 (2)
C10A—C11A1.3900C25A—H25B0.9500
C10A—H10B0.9500C26A—C27A1.39 (2)
C11A—C12A1.3900C26A—H26B0.9500
C11A—H11B0.9500C27A—N6A1.34 (3)
C12A—N3A1.3900C27A—H27B0.9500
C12A—H12B0.9500C28A—C291.729 (9)
C13A—C141.588 (14)C28A—H28C0.9900
C13A—H13C0.9900C28A—H28D0.9900
C13A—H13D0.9900C29—C301.265 (5)
C14—C151.302 (5)C29—H29A0.9500
C14—H14A0.9500C29—H29B0.9500
C14—H14B0.9500C30—H30A0.9500
C15—H15A0.9500C30—H30B0.9500
C15—H15B0.9500C30—H30C0.9500
C15—H15C0.9500C30—H30D0.9500
C15—H15D0.9500O1W—H1WB0.8450
Cu2—N41.999 (10)O1W—H1WA0.8630
N3—Cu1—N1119.5 (2)N4—Cu2—N6122.1 (4)
N1A—Cu1—N3A122.8 (7)N4—Cu2—Cl2123.4 (3)
N1A—Cu1—Cl1123.7 (5)N6A—Cu2—Cl2114.4 (5)
N3—Cu1—Cl1115.68 (17)N4A—Cu2—Cl2118.3 (4)
N1—Cu1—Cl1122.09 (18)N6—Cu2—Cl2111.2 (4)
N3A—Cu1—Cl1109.9 (5)N4—Cu2—N580.2 (3)
N1A—Cu1—N284.4 (4)N6A—Cu2—N582.3 (5)
N3—Cu1—N280.33 (16)N4A—Cu2—N578.2 (4)
N1—Cu1—N278.18 (17)N6—Cu2—N576.5 (3)
N3A—Cu1—N277.1 (4)Cl2—Cu2—N5132.70 (8)
Cl1—Cu1—N2128.12 (7)C21—N5—C22116.6 (4)
C7A—N2—C6A119.2 (8)C28A—N5—C21A116.5 (5)
C6—N2—C13113.5 (3)C21—N5—C28109.8 (4)
C6—N2—C7110.6 (3)C22—N5—C28108.0 (3)
C13—N2—C7108.1 (3)C28A—N5—C22A107.7 (4)
C7A—N2—C13A110.2 (8)C21A—N5—C22A104.3 (4)
C6A—N2—C13A105.9 (7)C21—N5—Cu2100.2 (3)
C7A—N2—Cu1110.4 (6)C28A—N5—Cu2120.5 (4)
C6A—N2—Cu199.9 (5)C22—N5—Cu2108.5 (2)
C6—N2—Cu1106.7 (2)C21A—N5—Cu2108.2 (3)
C13—N2—Cu1118.1 (2)C28—N5—Cu2113.7 (2)
C7—N2—Cu198.7 (2)C22A—N5—Cu296.3 (3)
C13A—N2—Cu1110.8 (5)N4—C20—C19123.6 (8)
C1—N1—C5117.2 (5)N4—C20—C21118.1 (8)
C1—N1—Cu1125.8 (5)C19—C20—C21118.2 (9)
C5—N1—Cu1117.0 (3)C16—N4—C20114.1 (8)
N1—C1—C2123.7 (7)C16—N4—Cu2132.1 (9)
N1—C1—H1A118.1C20—N4—Cu2113.6 (7)
C2—C1—H1A118.1N4—C16—C17129.1 (13)
C3—C2—C1117.9 (6)N4—C16—H16A115.5
C3—C2—H2A121.0C17—C16—H16A115.5
C1—C2—H2A121.0C16—C17—C18114.9 (12)
C4—C3—C2119.2 (6)C16—C17—H17A122.5
C4—C3—H3A120.4C18—C17—H17A122.5
C2—C3—H3A120.4C19—C18—C17119.3 (10)
C3—C4—C5120.1 (7)C19—C18—H18A120.4
C3—C4—H4A120.0C17—C18—H18A120.4
C5—C4—H4A120.0C18—C19—C20119.0 (11)
N1—C5—C4121.8 (5)C18—C19—H19A120.5
N1—C5—C6117.8 (4)C20—C19—H19A120.5
C4—C5—C6120.3 (5)N4A—C20A—C19A120.0
N2—C6—C5112.5 (4)N4A—C20A—C21A112.6 (9)
N2—C6—H6A109.1C19A—C20A—C21A126.4 (8)
C5—C6—H6A109.1C20A—N4A—C16A120.0
N2—C6—H6B109.1C20A—N4A—Cu2119.7 (7)
C5—C6—H6B109.1C16A—N4A—Cu2119.4 (7)
H6A—C6—H6B107.8N4A—C16A—C17A120.0
C8—C7—N2110.7 (3)N4A—C16A—H16B120.0
C8—C7—H7A109.5C17A—C16A—H16B120.0
N2—C7—H7A109.5C18A—C17A—C16A120.0
C8—C7—H7B109.5C18A—C17A—H17B120.0
N2—C7—H7B109.5C16A—C17A—H17B120.0
H7A—C7—H7B108.1C17A—C18A—C19A120.0
N3—C8—C9120.7 (4)C17A—C18A—H18B120.0
N3—C8—C7115.8 (4)C19A—C18A—H18B120.0
C9—C8—C7123.4 (4)C18A—C19A—C20A120.0
C10—C9—C8119.9 (5)C18A—C19A—H19B120.0
C10—C9—H9A120.0C20A—C19A—H19B120.0
C8—C9—H9A120.0N5—C21—C20112.1 (6)
C11—C10—C9119.1 (4)N5—C21—H21A109.2
C11—C10—H10A120.5C20—C21—H21A109.2
C9—C10—H10A120.5N5—C21—H21B109.2
C10—C11—C12117.8 (5)C20—C21—H21B109.2
C10—C11—H11A121.1H21A—C21—H21B107.9
C12—C11—H11A121.1N5—C22—C23109.9 (4)
N3—C12—C11124.8 (5)N5—C22—H22A109.7
N3—C12—H12A117.6C23—C22—H22A109.7
C11—C12—H12A117.6N5—C22—H22B109.7
C12—N3—C8117.6 (4)C23—C22—H22B109.7
C12—N3—Cu1127.0 (4)H22A—C22—H22B108.2
C8—N3—Cu1114.4 (4)N6—C23—C24122.0 (7)
N2—C13—C14108.6 (3)N6—C23—C22117.4 (6)
N2—C13—H13A110.0C24—C23—C22120.4 (5)
C14—C13—H13A110.0C25—C24—C23120.6 (10)
N2—C13—H13B110.0C25—C24—H24A119.7
C14—C13—H13B110.0C23—C24—H24A119.7
H13A—C13—H13B108.3C24—C25—C26118.9 (15)
C2A—C1A—N1A120.0C24—C25—H25A120.5
C2A—C1A—H1AA120.0C26—C25—H25A120.5
N1A—C1A—H1AA120.0C27—C26—C25119.1 (12)
C3A—C2A—C1A120.0C27—C26—H26A120.4
C3A—C2A—H2AA120.0C25—C26—H26A120.4
C1A—C2A—H2AA120.0N6—C27—C26122.9 (11)
C4A—C3A—C2A120.0N6—C27—H27A118.6
C4A—C3A—H3AA120.0C26—C27—H27A118.6
C2A—C3A—H3AA120.0C23—N6—C27116.3 (11)
C3A—C4A—C5A120.0C23—N6—Cu2117.5 (7)
C3A—C4A—H4AA120.0C27—N6—Cu2126.1 (9)
C5A—C4A—H4AA120.0C29—C28—N5107.8 (4)
N1A—C5A—C4A120.0C29—C28—H28A110.1
N1A—C5A—C6A114.7 (10)N5—C28—H28A110.1
C4A—C5A—C6A125.0 (10)C29—C28—H28B110.1
C5A—N1A—C1A120.0N5—C28—H28B110.1
C5A—N1A—Cu1113.7 (8)H28A—C28—H28B108.5
C1A—N1A—Cu1124.5 (8)N5—C21A—C20A114.9 (6)
N2—C6A—C5A114.5 (9)N5—C21A—H21C108.5
N2—C6A—H6AA108.6C20A—C21A—H21C108.5
C5A—C6A—H6AA108.6N5—C21A—H21D108.5
N2—C6A—H6AB108.6C20A—C21A—H21D108.5
C5A—C6A—H6AB108.6H21C—C21A—H21D107.5
H6AA—C6A—H6AB107.6C23A—C22A—N5108.9 (5)
N2—C7A—C8A108.6 (10)C23A—C22A—H22C109.9
N2—C7A—H7AA110.0N5—C22A—H22C109.9
C8A—C7A—H7AA110.0C23A—C22A—H22D109.9
N2—C7A—H7AB110.0N5—C22A—H22D109.9
C8A—C7A—H7AB110.0H22C—C22A—H22D108.3
H7AA—C7A—H7AB108.4N6A—C23A—C24A121.6 (11)
C9A—C8A—N3A120.0N6A—C23A—C22A115.3 (9)
C9A—C8A—C7A121.8 (10)C24A—C23A—C22A123.1 (8)
N3A—C8A—C7A117.2 (10)C23A—C24A—C25A118.8 (13)
C8A—C9A—C10A120.0C23A—C24A—H24B120.6
C8A—C9A—H9AA120.0C25A—C24A—H24B120.6
C10A—C9A—H9AA120.0C26A—C25A—C24A118.2 (19)
C11A—C10A—C9A120.0C26A—C25A—H25B120.9
C11A—C10A—H10B120.0C24A—C25A—H25B120.9
C9A—C10A—H10B120.0C25A—C26A—C27A118.8 (16)
C10A—C11A—C12A120.0C25A—C26A—H26B120.6
C10A—C11A—H11B120.0C27A—C26A—H26B120.6
C12A—C11A—H11B120.0N6A—C27A—C26A123.8 (14)
C11A—C12A—N3A120.0N6A—C27A—H27B118.1
C11A—C12A—H12B120.0C26A—C27A—H27B118.1
N3A—C12A—H12B120.0C23A—N6A—C27A118.6 (14)
C12A—N3A—C8A120.0C23A—N6A—Cu2114.4 (10)
C12A—N3A—Cu1124.6 (9)C27A—N6A—Cu2122.1 (13)
C8A—N3A—Cu1114.6 (9)N5—C28A—C29103.0 (5)
C14—C13A—N2100.2 (7)N5—C28A—H28C111.2
C14—C13A—H13C111.7C29—C28A—H28C111.2
N2—C13A—H13C111.7N5—C28A—H28D111.2
C14—C13A—H13D111.7C29—C28A—H28D111.2
N2—C13A—H13D111.7H28C—C28A—H28D109.1
H13C—C13A—H13D109.5C30—C29—C28117.1 (5)
C15—C14—C13122.3 (4)C30—C29—C28A117.4 (5)
C15—C14—C13A110.1 (6)C30—C29—H29A121.4
C15—C14—H14A118.9C28—C29—H29A121.4
C13—C14—H14A118.9C30—C29—H29B121.3
C15—C14—H14B124.9C28A—C29—H29B121.3
C13A—C14—H14B124.9C29—C30—H30A120.0
C14—C15—H15A120.0C29—C30—H30B120.0
C14—C15—H15B120.0H30A—C30—H30B120.0
H15A—C15—H15B120.0C29—C30—H30C120.0
C14—C15—H15C120.0C29—C30—H30D120.0
C14—C15—H15D120.0H30C—C30—H30D120.0
H15C—C15—H15D120.0H1WB—O1W—H1WA123.6
N6A—Cu2—N4A122.8 (5)
C5—N1—C1—C21.3 (8)C19—C20—N4—C160.4 (15)
Cu1—N1—C1—C2176.5 (5)C21—C20—N4—C16176.5 (10)
N1—C1—C2—C32.6 (9)C19—C20—N4—Cu2174.8 (8)
C1—C2—C3—C41.5 (10)C21—C20—N4—Cu29.1 (11)
C2—C3—C4—C50.6 (10)C20—N4—C16—C170.2 (17)
C1—N1—C5—C40.9 (9)Cu2—N4—C16—C17172.8 (11)
Cu1—N1—C5—C4178.9 (5)N4—C16—C17—C181.7 (18)
C1—N1—C5—C6175.5 (5)C16—C17—C18—C192.5 (19)
Cu1—N1—C5—C62.5 (7)C17—C18—C19—C202.1 (19)
C3—C4—C5—N11.9 (10)N4—C20—C19—C180.5 (17)
C3—C4—C5—C6174.4 (6)C21—C20—C19—C18175.6 (12)
C13—N2—C6—C5161.6 (4)C19A—C20A—N4A—C16A0.0
C7—N2—C6—C576.6 (4)C21A—C20A—N4A—C16A169.3 (10)
Cu1—N2—C6—C529.7 (4)C19A—C20A—N4A—Cu2169.0 (8)
N1—C5—C6—N223.6 (7)C21A—C20A—N4A—Cu221.7 (10)
C4—C5—C6—N2159.9 (5)C20A—N4A—C16A—C17A0.0
C6—N2—C7—C8157.5 (3)Cu2—N4A—C16A—C17A169.0 (8)
C13—N2—C7—C877.6 (4)N4A—C16A—C17A—C18A0.0
Cu1—N2—C7—C845.9 (3)C16A—C17A—C18A—C19A0.0
N2—C7—C8—N343.8 (6)C17A—C18A—C19A—C20A0.0
N2—C7—C8—C9138.9 (5)N4A—C20A—C19A—C18A0.0
N3—C8—C9—C100.6 (10)C21A—C20A—C19A—C18A167.7 (12)
C7—C8—C9—C10177.7 (6)C22—N5—C21—C20157.8 (5)
C8—C9—C10—C110.0 (11)C28—N5—C21—C2079.0 (6)
C9—C10—C11—C120.8 (11)Cu2—N5—C21—C2040.9 (5)
C10—C11—C12—N31.3 (12)N4—C20—C21—N538.7 (10)
C11—C12—N3—C80.8 (10)C19—C20—C21—N5144.9 (7)
C11—C12—N3—Cu1167.2 (6)C21—N5—C22—C2378.4 (6)
C9—C8—N3—C120.2 (9)C28—N5—C22—C23157.5 (4)
C7—C8—N3—C12177.5 (6)Cu2—N5—C22—C2333.8 (5)
C9—C8—N3—Cu1169.7 (4)N5—C22—C23—N627.1 (9)
C7—C8—N3—Cu112.9 (6)N5—C22—C23—C24157.2 (6)
C6—N2—C13—C1470.4 (4)N6—C23—C24—C250.5 (15)
C7—N2—C13—C14166.4 (3)C22—C23—C24—C25175.0 (11)
Cu1—N2—C13—C1455.6 (4)C23—C24—C25—C261 (2)
N1A—C1A—C2A—C3A0.0C24—C25—C26—C274 (2)
C1A—C2A—C3A—C4A0.0C25—C26—C27—N65.2 (19)
C2A—C3A—C4A—C5A0.0C24—C23—N6—C270.5 (14)
C3A—C4A—C5A—N1A0.0C22—C23—N6—C27176.2 (9)
C3A—C4A—C5A—C6A173.4 (14)C24—C23—N6—Cu2180.0 (6)
C4A—C5A—N1A—C1A0.0C22—C23—N6—Cu24.3 (10)
C6A—C5A—N1A—C1A174.0 (12)C26—C27—N6—C233.4 (17)
C4A—C5A—N1A—Cu1165.3 (12)C26—C27—N6—Cu2177.2 (8)
C6A—C5A—N1A—Cu120.6 (12)C21—N5—C28—C29173.0 (4)
C2A—C1A—N1A—C5A0.0C22—N5—C28—C2958.9 (5)
C2A—C1A—N1A—Cu1163.7 (13)Cu2—N5—C28—C2961.6 (4)
C7A—N2—C6A—C5A155.2 (10)C28A—N5—C21A—C20A162.0 (7)
C13A—N2—C6A—C5A80.1 (11)C22A—N5—C21A—C20A79.3 (8)
Cu1—N2—C6A—C5A35.1 (10)Cu2—N5—C21A—C20A22.4 (8)
N1A—C5A—C6A—N241.2 (13)N4A—C20A—C21A—N529.3 (9)
C4A—C5A—C6A—N2145.2 (11)C19A—C20A—C21A—N5162.2 (7)
C6A—N2—C7A—C8A80.0 (12)C28A—N5—C22A—C23A78.6 (7)
C13A—N2—C7A—C8A157.4 (9)C21A—N5—C22A—C23A156.9 (6)
Cu1—N2—C7A—C8A34.7 (11)Cu2—N5—C22A—C23A46.3 (5)
N2—C7A—C8A—C9A153.1 (10)N5—C22A—C23A—N6A51.5 (9)
N2—C7A—C8A—N3A38.3 (14)N5—C22A—C23A—C24A129.7 (7)
N3A—C8A—C9A—C10A0.0N6A—C23A—C24A—C25A0.1 (18)
C7A—C8A—C9A—C10A168.3 (15)C22A—C23A—C24A—C25A178.8 (15)
C8A—C9A—C10A—C11A0.0C23A—C24A—C25A—C26A1 (3)
C9A—C10A—C11A—C12A0.0C24A—C25A—C26A—C27A4 (3)
C10A—C11A—C12A—N3A0.0C25A—C26A—C27A—N6A5 (2)
C11A—C12A—N3A—C8A0.0C24A—C23A—N6A—C27A1.2 (16)
C11A—C12A—N3A—Cu1169.2 (12)C22A—C23A—N6A—C27A180.0 (11)
C9A—C8A—N3A—C12A0.0C24A—C23A—N6A—Cu2157.1 (7)
C7A—C8A—N3A—C12A168.8 (15)C22A—C23A—N6A—Cu224.1 (10)
C9A—C8A—N3A—Cu1170.2 (11)C26A—C27A—N6A—C23A4 (2)
C7A—C8A—N3A—Cu120.9 (14)C26A—C27A—N6A—Cu2157.8 (11)
C7A—N2—C13A—C1451.5 (10)C21A—N5—C28A—C2973.4 (6)
C6A—N2—C13A—C14178.3 (7)C22A—N5—C28A—C29169.9 (4)
Cu1—N2—C13A—C1470.9 (7)Cu2—N5—C28A—C2961.0 (5)
N2—C13—C14—C15140.7 (4)N5—C28—C29—C30147.2 (5)
N2—C13A—C14—C15154.8 (5)N5—C28A—C29—C30151.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WB···Cl1i0.852.353.199 (8)177
O1W—H1WA···Cl20.862.163.027 (8)179
Symmetry code: (i) x, y1, z.
(2) catena-Poly[[copper(I)-µ2-(prop-2-en-1-yl)bis[pyridin-2-yl)methylidene]amine-κ5N,N',N'':C2,C3] perchlorate acetonitrile monosolvate] top
Crystal data top
[Cu(C15H17N3)]ClO4·C2H3NF(000) = 912
Mr = 443.37Dx = 1.527 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.2961 (5) ÅCell parameters from 9978 reflections
b = 10.7435 (6) Åθ = 2.2–29.8°
c = 17.5025 (9) ŵ = 1.30 mm1
β = 94.932 (3)°T = 150 K
V = 1928.89 (17) Å3Rhomboid, grey
Z = 40.51 × 0.28 × 0.17 mm
Data collection top
Bruker SMART APEXII
diffractometer
5517 independent reflections
Radiation source: fine-focus sealed tube4802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 8.33 pixels mm-1θmax = 29.8°, θmin = 2.0°
φ and ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1515
Tmin = 0.554, Tmax = 0.807l = 2424
27703 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0419P)2 + 1.3152P]
where P = (Fo2 + 2Fc2)/3
5517 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.45 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.40952 (2)0.28116 (2)0.18876 (2)0.02180 (7)
N10.35487 (14)0.35540 (13)0.08578 (8)0.0232 (3)
N20.35542 (12)0.47632 (12)0.22597 (7)0.0188 (2)
N30.25255 (13)0.24543 (13)0.24709 (8)0.0213 (3)
C10.38255 (19)0.30569 (17)0.01841 (10)0.0298 (4)
H10.42330.22630.01840.036*
C20.3539 (2)0.3658 (2)0.05060 (11)0.0362 (4)
H20.37310.32790.09730.043*
C30.2969 (2)0.4822 (2)0.05060 (11)0.0389 (5)
H30.27600.52530.09740.047*
C40.27066 (19)0.53545 (18)0.01861 (11)0.0319 (4)
H40.23320.61620.01990.038*
C50.29974 (15)0.46931 (15)0.08566 (9)0.0219 (3)
C60.26267 (15)0.51606 (15)0.16191 (9)0.0225 (3)
H6A0.25890.60810.16070.027*
H6B0.17470.48480.17060.027*
C70.29044 (16)0.45596 (16)0.29639 (9)0.0237 (3)
H7A0.23320.52770.30510.028*
H7B0.35670.44980.34070.028*
C80.21024 (16)0.33811 (16)0.29040 (9)0.0231 (3)
C90.10020 (18)0.32522 (19)0.33018 (11)0.0323 (4)
H90.07060.39270.35920.039*
C100.0339 (2)0.2129 (2)0.32709 (13)0.0392 (5)
H100.04090.20200.35460.047*
C110.07809 (19)0.11698 (19)0.28341 (12)0.0344 (4)
H110.03450.03900.28060.041*
C120.18699 (17)0.13676 (16)0.24387 (10)0.0259 (3)
H120.21660.07130.21330.031*
C130.46963 (15)0.56005 (14)0.23791 (9)0.0207 (3)
H13A0.51890.55690.19180.025*
H13B0.52760.52860.28170.025*
C140.43571 (17)0.69412 (16)0.25335 (11)0.0268 (3)
H140.43630.75250.21260.032*
C150.40412 (19)0.73514 (19)0.32348 (14)0.0381 (5)
H15A0.38980.67030.36200.046*
H15B0.34100.80470.32320.046*
Cl10.31067 (4)0.91688 (4)0.06230 (2)0.03084 (10)
O10.20483 (18)0.8654 (2)0.10057 (11)0.0607 (5)
O20.2754 (2)0.9252 (3)0.01744 (10)0.0768 (7)
O30.33879 (19)1.03794 (16)0.09251 (11)0.0543 (4)
O40.4244 (2)0.8414 (2)0.07888 (14)0.0776 (7)
N40.0428 (3)0.1619 (3)0.63275 (19)0.0916 (11)
C160.0056 (3)0.2326 (2)0.59215 (16)0.0504 (6)
C170.0424 (3)0.3246 (4)0.54240 (18)0.0686 (9)
H17A0.07590.39600.57280.103*
H17B0.02860.35190.50530.103*
H17C0.11260.28870.51510.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02294 (11)0.01788 (10)0.02509 (11)0.00372 (7)0.00491 (7)0.00274 (7)
N10.0275 (7)0.0196 (6)0.0229 (6)0.0009 (5)0.0047 (5)0.0007 (5)
N20.0188 (6)0.0170 (6)0.0208 (6)0.0014 (5)0.0023 (5)0.0006 (5)
N30.0221 (6)0.0178 (6)0.0240 (6)0.0014 (5)0.0026 (5)0.0004 (5)
C10.0373 (9)0.0259 (8)0.0271 (8)0.0005 (7)0.0086 (7)0.0019 (7)
C20.0465 (11)0.0391 (11)0.0238 (8)0.0055 (9)0.0079 (7)0.0012 (7)
C30.0502 (12)0.0410 (11)0.0249 (8)0.0032 (9)0.0008 (8)0.0098 (8)
C40.0382 (10)0.0258 (8)0.0310 (9)0.0011 (7)0.0019 (7)0.0074 (7)
C50.0219 (7)0.0183 (7)0.0250 (7)0.0019 (6)0.0004 (6)0.0009 (6)
C60.0206 (7)0.0194 (7)0.0271 (7)0.0031 (6)0.0006 (6)0.0017 (6)
C70.0270 (8)0.0206 (7)0.0243 (7)0.0041 (6)0.0076 (6)0.0039 (6)
C80.0233 (7)0.0220 (7)0.0245 (7)0.0032 (6)0.0041 (6)0.0006 (6)
C90.0303 (9)0.0315 (9)0.0370 (9)0.0049 (7)0.0135 (7)0.0066 (8)
C100.0344 (10)0.0383 (11)0.0476 (11)0.0123 (8)0.0191 (9)0.0034 (9)
C110.0325 (9)0.0291 (9)0.0424 (10)0.0114 (7)0.0072 (8)0.0000 (8)
C120.0271 (8)0.0201 (7)0.0302 (8)0.0034 (6)0.0021 (6)0.0010 (6)
C130.0198 (7)0.0181 (7)0.0244 (7)0.0018 (5)0.0017 (5)0.0004 (6)
C140.0230 (8)0.0183 (7)0.0384 (9)0.0031 (6)0.0011 (7)0.0008 (6)
C150.0277 (9)0.0296 (9)0.0590 (13)0.0084 (7)0.0158 (9)0.0159 (9)
Cl10.0350 (2)0.0286 (2)0.0300 (2)0.00178 (17)0.00879 (16)0.00400 (16)
O10.0505 (10)0.0695 (13)0.0646 (11)0.0199 (9)0.0189 (9)0.0112 (10)
O20.0803 (14)0.124 (2)0.0261 (8)0.0273 (14)0.0027 (8)0.0102 (10)
O30.0721 (12)0.0338 (8)0.0570 (10)0.0100 (8)0.0053 (9)0.0107 (7)
O40.0690 (13)0.0750 (15)0.0933 (16)0.0398 (12)0.0332 (12)0.0171 (13)
N40.107 (2)0.0626 (17)0.096 (2)0.0386 (16)0.0445 (18)0.0344 (16)
C160.0511 (14)0.0400 (12)0.0558 (14)0.0056 (10)0.0210 (11)0.0050 (11)
C170.0456 (14)0.098 (2)0.0607 (16)0.0108 (15)0.0048 (12)0.0264 (17)
Geometric parameters (Å, º) top
Cu1—N12.0067 (14)C8—C91.387 (2)
Cu1—C15i2.0107 (19)C9—C101.385 (3)
Cu1—N32.0211 (14)C9—H90.9500
Cu1—C14i2.0403 (17)C10—C111.384 (3)
Cu1—N22.2788 (13)C10—H100.9500
N1—C11.347 (2)C11—C121.384 (2)
N1—C51.349 (2)C11—H110.9500
N2—C71.468 (2)C12—H120.9500
N2—C61.472 (2)C13—C141.512 (2)
N2—C131.4810 (19)C13—H13A0.9900
N3—C81.346 (2)C13—H13B0.9900
N3—C121.347 (2)C14—C151.369 (3)
C1—C21.379 (3)C14—Cu1ii2.0403 (17)
C1—H10.9500C14—H140.9500
C2—C31.381 (3)C15—Cu1ii2.0106 (19)
C2—H20.9500C15—H15A0.9900
C3—C41.387 (3)C15—H15B0.9900
C3—H30.9500Cl1—O21.4144 (18)
C4—C51.382 (2)Cl1—O31.4242 (17)
C4—H40.9500Cl1—O41.434 (2)
C5—C61.505 (2)Cl1—O11.4379 (17)
C6—H6A0.9900N4—C161.129 (4)
C6—H6B0.9900C16—C171.433 (4)
C7—C81.510 (2)C17—H17A0.9800
C7—H7A0.9900C17—H17B0.9800
C7—H7B0.9900C17—H17C0.9800
N1—Cu1—C15i101.45 (8)H7A—C7—H7B108.1
N1—Cu1—N3110.76 (6)N3—C8—C9121.78 (16)
C15i—Cu1—N3144.98 (7)N3—C8—C7117.24 (14)
N1—Cu1—C14i140.80 (7)C9—C8—C7120.94 (15)
C15i—Cu1—C14i39.50 (8)C10—C9—C8119.25 (18)
N3—Cu1—C14i106.64 (7)C10—C9—H9120.4
N1—Cu1—N280.47 (5)C8—C9—H9120.4
C15i—Cu1—N2121.04 (7)C11—C10—C9119.09 (17)
N3—Cu1—N278.74 (5)C11—C10—H10120.5
C14i—Cu1—N2118.65 (6)C9—C10—H10120.5
C1—N1—C5118.62 (15)C10—C11—C12118.76 (17)
C1—N1—Cu1124.37 (12)C10—C11—H11120.6
C5—N1—Cu1116.58 (11)C12—C11—H11120.6
C7—N2—C6111.72 (13)N3—C12—C11122.46 (16)
C7—N2—C13112.68 (12)N3—C12—H12118.8
C6—N2—C13112.73 (12)C11—C12—H12118.8
C7—N2—Cu1104.06 (9)N2—C13—C14114.27 (13)
C6—N2—Cu1101.98 (9)N2—C13—H13A108.7
C13—N2—Cu1112.86 (9)C14—C13—H13A108.7
C8—N3—C12118.63 (14)N2—C13—H13B108.7
C8—N3—Cu1117.09 (11)C14—C13—H13B108.7
C12—N3—Cu1124.26 (12)H13A—C13—H13B107.6
N1—C1—C2122.37 (18)C15—C14—C13122.90 (17)
N1—C1—H1118.8C15—C14—Cu1ii69.08 (11)
C2—C1—H1118.8C13—C14—Cu1ii110.06 (11)
C1—C2—C3118.89 (18)C15—C14—H14118.5
C1—C2—H2120.6C13—C14—H14118.5
C3—C2—H2120.6Cu1ii—C14—H1490.8
C2—C3—C4119.20 (17)C14—C15—Cu1ii71.41 (11)
C2—C3—H3120.4C14—C15—H15A116.5
C4—C3—H3120.4Cu1ii—C15—H15A116.5
C5—C4—C3119.03 (18)C14—C15—H15B116.5
C5—C4—H4120.5Cu1ii—C15—H15B116.5
C3—C4—H4120.5H15A—C15—H15B113.5
N1—C5—C4121.87 (16)O2—Cl1—O3109.59 (14)
N1—C5—C6116.11 (14)O2—Cl1—O4111.79 (15)
C4—C5—C6121.87 (15)O3—Cl1—O4107.77 (15)
N2—C6—C5112.40 (13)O2—Cl1—O1110.09 (13)
N2—C6—H6A109.1O3—Cl1—O1108.44 (12)
C5—C6—H6A109.1O4—Cl1—O1109.08 (13)
N2—C6—H6B109.1N4—C16—C17178.4 (3)
C5—C6—H6B109.1C16—C17—H17A109.5
H6A—C6—H6B107.9C16—C17—H17B109.5
N2—C7—C8110.63 (13)H17A—C17—H17B109.5
N2—C7—H7A109.5C16—C17—H17C109.5
C8—C7—H7A109.5H17A—C17—H17C109.5
N2—C7—H7B109.5H17B—C17—H17C109.5
C8—C7—H7B109.5
C5—N1—C1—C21.5 (3)C12—N3—C8—C91.3 (2)
Cu1—N1—C1—C2173.66 (15)Cu1—N3—C8—C9177.28 (14)
N1—C1—C2—C31.2 (3)C12—N3—C8—C7176.54 (15)
C1—C2—C3—C40.3 (3)Cu1—N3—C8—C74.89 (19)
C2—C3—C4—C51.4 (3)N2—C7—C8—N330.6 (2)
C1—N1—C5—C40.3 (2)N2—C7—C8—C9151.58 (17)
Cu1—N1—C5—C4173.09 (14)N3—C8—C9—C101.8 (3)
C1—N1—C5—C6175.93 (15)C7—C8—C9—C10175.95 (19)
Cu1—N1—C5—C611.28 (18)C8—C9—C10—C110.9 (3)
C3—C4—C5—N11.1 (3)C9—C10—C11—C120.3 (3)
C3—C4—C5—C6174.26 (17)C8—N3—C12—C110.1 (3)
C7—N2—C6—C5147.18 (13)Cu1—N3—C12—C11178.52 (14)
C13—N2—C6—C584.73 (16)C10—C11—C12—N30.9 (3)
Cu1—N2—C6—C536.57 (14)C7—N2—C13—C1469.43 (18)
N1—C5—C6—N235.3 (2)C6—N2—C13—C1458.16 (18)
C4—C5—C6—N2149.04 (16)Cu1—N2—C13—C14173.05 (11)
C6—N2—C7—C872.93 (17)N2—C13—C14—C1578.8 (2)
C13—N2—C7—C8158.95 (13)N2—C13—C14—Cu1ii156.32 (11)
Cu1—N2—C7—C836.35 (15)C13—C14—C15—Cu1ii100.95 (16)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2.
(3) Dichlorido{(prop-2-en-1-yl)bis[pyridin-2-yl)methylidene]amine-κ3N,N',N''}copper(II) dichloromethane monosolvate top
Crystal data top
[CuCl2(C15H17N3)]·CH2Cl2F(000) = 932
Mr = 458.68Dx = 1.546 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.3756 (3) ÅCell parameters from 9541 reflections
b = 11.0380 (4) Åθ = 2.5–31.8°
c = 21.6954 (9) ŵ = 1.65 mm1
β = 100.749 (1)°T = 150 K
V = 1970.54 (13) Å3Rhomboid, blue
Z = 40.31 × 0.07 × 0.06 mm
Data collection top
Bruker SMART APEXII
diffractometer
6852 independent reflections
Radiation source: fine-focus sealed tube5778 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 32.7°, θmin = 1.9°
φ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1616
Tmin = 0.870, Tmax = 0.906l = 3232
24724 measured reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0331P)2 + 1.6661P]
where P = (Fo2 + 2Fc2)/3
6852 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 1.33 e Å3
0 restraintsΔρmin = 1.01 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.34016 (2)0.33733 (2)0.15325 (2)0.02093 (5)
Cl10.27627 (6)0.51397 (4)0.10199 (2)0.03532 (10)
Cl20.50436 (5)0.40163 (3)0.26031 (2)0.02295 (8)
N10.13632 (16)0.31992 (12)0.18776 (7)0.0229 (3)
N20.35799 (16)0.15602 (12)0.17680 (6)0.0193 (2)
N30.53041 (17)0.29320 (13)0.11324 (6)0.0226 (3)
C10.00884 (19)0.39636 (15)0.17976 (8)0.0249 (3)
H10.00420.46030.15010.030*
C20.1150 (2)0.38486 (16)0.21316 (9)0.0273 (3)
H20.20410.43960.20650.033*
C30.1075 (2)0.29200 (16)0.25673 (9)0.0278 (3)
H30.18910.28460.28160.033*
C40.0202 (2)0.21010 (16)0.26365 (8)0.0250 (3)
H40.02540.14420.29210.030*
C50.14009 (19)0.22653 (14)0.22813 (8)0.0217 (3)
C60.28549 (19)0.14372 (14)0.23395 (7)0.0214 (3)
H6A0.36670.16570.27160.026*
H6B0.25170.05880.23860.026*
C70.53397 (18)0.12954 (14)0.18688 (7)0.0208 (3)
H7A0.55180.04090.18620.025*
H7B0.58830.16110.22820.025*
C80.60363 (19)0.18920 (14)0.13543 (7)0.0208 (3)
C90.7351 (2)0.14239 (16)0.11285 (8)0.0266 (3)
H90.78440.06850.12880.032*
C100.7932 (2)0.20586 (19)0.06633 (9)0.0318 (4)
H100.88340.17590.05010.038*
C110.7187 (2)0.31286 (19)0.04380 (9)0.0333 (4)
H110.75730.35760.01210.040*
C120.5870 (2)0.35377 (17)0.06808 (8)0.0282 (3)
H120.53500.42690.05230.034*
C130.2659 (2)0.08322 (16)0.12335 (8)0.0258 (3)
H13A0.14850.10050.11960.031*
H13B0.29880.11010.08400.031*
C140.2916 (2)0.05088 (16)0.12997 (9)0.0301 (4)
H140.25510.09120.16350.036*
C150.3623 (3)0.1158 (2)0.09167 (11)0.0415 (5)
H15A0.39990.07770.05780.050*
H15B0.37560.20070.09790.050*
C160.9240 (3)0.7454 (2)0.09385 (11)0.0477 (6)
H16A0.97140.78010.13530.057*
H16B1.00710.69260.08070.057*
Cl30.75172 (11)0.65644 (7)0.10123 (4)0.0697 (2)
Cl40.87639 (10)0.86418 (8)0.03914 (3)0.06430 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02180 (9)0.01790 (9)0.02352 (10)0.00296 (7)0.00535 (7)0.00421 (7)
Cl10.0427 (2)0.0279 (2)0.0370 (2)0.01079 (18)0.01161 (19)0.01457 (17)
Cl20.02182 (16)0.02201 (17)0.02533 (17)0.00270 (13)0.00520 (13)0.00099 (13)
N10.0195 (6)0.0201 (6)0.0284 (7)0.0008 (5)0.0030 (5)0.0001 (5)
N20.0189 (5)0.0184 (6)0.0205 (6)0.0009 (5)0.0032 (4)0.0009 (4)
N30.0247 (6)0.0220 (6)0.0214 (6)0.0007 (5)0.0051 (5)0.0021 (5)
C10.0216 (7)0.0213 (7)0.0302 (8)0.0029 (6)0.0002 (6)0.0019 (6)
C20.0193 (7)0.0255 (8)0.0357 (9)0.0022 (6)0.0013 (6)0.0085 (7)
C30.0215 (7)0.0281 (8)0.0346 (9)0.0041 (6)0.0076 (6)0.0096 (7)
C40.0228 (7)0.0235 (7)0.0297 (8)0.0038 (6)0.0079 (6)0.0037 (6)
C50.0193 (6)0.0193 (7)0.0264 (7)0.0006 (5)0.0038 (5)0.0016 (6)
C60.0211 (7)0.0197 (7)0.0241 (7)0.0011 (5)0.0059 (5)0.0032 (5)
C70.0198 (6)0.0197 (6)0.0228 (7)0.0018 (5)0.0039 (5)0.0015 (5)
C80.0212 (7)0.0214 (7)0.0196 (6)0.0001 (5)0.0037 (5)0.0007 (5)
C90.0263 (8)0.0284 (8)0.0259 (8)0.0032 (6)0.0072 (6)0.0024 (6)
C100.0308 (8)0.0404 (10)0.0270 (8)0.0016 (8)0.0125 (7)0.0034 (7)
C110.0372 (9)0.0408 (10)0.0243 (8)0.0019 (8)0.0124 (7)0.0037 (7)
C120.0326 (8)0.0285 (8)0.0243 (8)0.0002 (7)0.0074 (6)0.0056 (6)
C130.0244 (7)0.0257 (8)0.0251 (7)0.0005 (6)0.0011 (6)0.0024 (6)
C140.0346 (9)0.0240 (8)0.0305 (8)0.0040 (7)0.0030 (7)0.0035 (6)
C150.0517 (12)0.0328 (10)0.0382 (10)0.0028 (9)0.0036 (9)0.0102 (8)
C160.0525 (13)0.0514 (14)0.0369 (11)0.0166 (11)0.0023 (10)0.0000 (10)
Cl30.0745 (5)0.0508 (4)0.0827 (5)0.0011 (3)0.0116 (4)0.0083 (3)
Cl40.0738 (4)0.0800 (5)0.0380 (3)0.0240 (4)0.0074 (3)0.0170 (3)
Geometric parameters (Å, º) top
Cu1—N11.9972 (14)C7—C81.504 (2)
Cu1—N32.0114 (14)C7—H7A0.9900
Cu1—N22.0640 (13)C7—H7B0.9900
Cu1—Cl12.2590 (5)C8—C91.386 (2)
Cu1—Cl22.5688 (4)C9—C101.389 (3)
N1—C11.346 (2)C9—H90.9500
N1—C51.349 (2)C10—C111.382 (3)
N2—C71.478 (2)C10—H100.9500
N2—C61.485 (2)C11—C121.384 (3)
N2—C131.500 (2)C11—H110.9500
N3—C121.343 (2)C12—H120.9500
N3—C81.347 (2)C13—C141.499 (2)
C1—C21.378 (2)C13—H13A0.9900
C1—H10.9500C13—H13B0.9900
C2—C31.388 (3)C14—C151.318 (3)
C2—H20.9500C14—H140.9500
C3—C41.387 (2)C15—H15A0.9500
C3—H30.9500C15—H15B0.9500
C4—C51.387 (2)C16—Cl41.763 (2)
C4—H40.9500C16—Cl31.777 (3)
C5—C61.509 (2)C16—H16A0.9900
C6—H6A0.9900C16—H16B0.9900
C6—H6B0.9900
N1—Cu1—N3160.02 (6)C5—C6—H6B109.9
N1—Cu1—N280.87 (5)H6A—C6—H6B108.3
N3—Cu1—N281.11 (5)N2—C7—C8108.52 (12)
N1—Cu1—Cl197.30 (4)N2—C7—H7A110.0
N3—Cu1—Cl197.50 (4)C8—C7—H7A110.0
N2—Cu1—Cl1163.41 (4)N2—C7—H7B110.0
N1—Cu1—Cl292.21 (4)C8—C7—H7B110.0
N3—Cu1—Cl297.09 (4)H7A—C7—H7B108.4
N2—Cu1—Cl292.42 (4)N3—C8—C9122.01 (15)
Cl1—Cu1—Cl2104.146 (18)N3—C8—C7115.11 (13)
C1—N1—C5118.97 (15)C9—C8—C7122.88 (15)
C1—N1—Cu1127.17 (12)C8—C9—C10118.54 (17)
C5—N1—Cu1113.50 (10)C8—C9—H9120.7
C7—N2—C6114.21 (12)C10—C9—H9120.7
C7—N2—C13111.28 (12)C11—C10—C9119.48 (17)
C6—N2—C13111.42 (12)C11—C10—H10120.3
C7—N2—Cu1104.62 (9)C9—C10—H10120.3
C6—N2—Cu1105.86 (9)C10—C11—C12118.92 (17)
C13—N2—Cu1108.96 (10)C10—C11—H11120.5
C12—N3—C8119.05 (15)C12—C11—H11120.5
C12—N3—Cu1127.58 (12)N3—C12—C11122.00 (17)
C8—N3—Cu1113.36 (11)N3—C12—H12119.0
N1—C1—C2122.10 (16)C11—C12—H12119.0
N1—C1—H1118.9C14—C13—N2114.27 (14)
C2—C1—H1118.9C14—C13—H13A108.7
C1—C2—C3118.89 (16)N2—C13—H13A108.7
C1—C2—H2120.6C14—C13—H13B108.7
C3—C2—H2120.6N2—C13—H13B108.7
C4—C3—C2119.44 (16)H13A—C13—H13B107.6
C4—C3—H3120.3C15—C14—C13123.34 (19)
C2—C3—H3120.3C15—C14—H14118.3
C3—C4—C5118.56 (16)C13—C14—H14118.3
C3—C4—H4120.7C14—C15—H15A120.0
C5—C4—H4120.7C14—C15—H15B120.0
N1—C5—C4121.93 (15)H15A—C15—H15B120.0
N1—C5—C6115.97 (14)Cl4—C16—Cl3112.71 (13)
C4—C5—C6122.07 (15)Cl4—C16—H16A109.1
N2—C6—C5108.91 (12)Cl3—C16—H16A109.1
N2—C6—H6A109.9Cl4—C16—H16B109.1
C5—C6—H6A109.9Cl3—C16—H16B109.1
N2—C6—H6B109.9H16A—C16—H16B107.8
C5—N1—C1—C22.4 (2)Cu1—N2—C7—C843.26 (13)
Cu1—N1—C1—C2170.21 (13)C12—N3—C8—C90.4 (2)
N1—C1—C2—C30.4 (3)Cu1—N3—C8—C9178.74 (13)
C1—C2—C3—C42.8 (2)C12—N3—C8—C7178.67 (15)
C2—C3—C4—C52.3 (2)Cu1—N3—C8—C72.23 (17)
C1—N1—C5—C42.9 (2)N2—C7—C8—N331.65 (18)
Cu1—N1—C5—C4170.69 (12)N2—C7—C8—C9149.33 (15)
C1—N1—C5—C6179.16 (14)N3—C8—C9—C100.6 (3)
Cu1—N1—C5—C67.25 (18)C7—C8—C9—C10178.36 (16)
C3—C4—C5—N10.5 (2)C8—C9—C10—C110.2 (3)
C3—C4—C5—C6178.35 (15)C9—C10—C11—C120.3 (3)
C7—N2—C6—C5152.60 (13)C8—N3—C12—C110.2 (3)
C13—N2—C6—C580.27 (15)Cu1—N3—C12—C11179.20 (14)
Cu1—N2—C6—C538.05 (14)C10—C11—C12—N30.6 (3)
N1—C5—C6—N221.73 (19)C7—N2—C13—C1455.61 (19)
C4—C5—C6—N2160.33 (14)C6—N2—C13—C1473.10 (18)
C6—N2—C7—C8158.54 (13)Cu1—N2—C13—C14170.46 (12)
C13—N2—C7—C874.25 (16)N2—C13—C14—C15115.3 (2)
(4) Chlorido{(prop-2-en-1-yl)bis[pyridin-2-yl)methylidene]amine-κ3N,N',N''}copper(II) perchlorate top
Crystal data top
[CuCl(C15H17N3)]ClO4F(000) = 892
Mr = 437.76Dx = 1.696 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 8.4260 (12) ÅCell parameters from 4302 reflections
b = 14.832 (2) Åθ = 2.7–30.1°
c = 14.007 (2) ŵ = 1.61 mm1
β = 101.677 (2)°T = 150 K
V = 1714.3 (4) Å3Rhomboid, blue
Z = 40.25 × 0.20 × 0.06 mm
Data collection top
Bruker SMART APEXII
diffractometer
5553 independent reflections
Radiation source: fine-focus sealed tube4766 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.33 pixels mm-1θmax = 32.6°, θmin = 2.8°
φ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 2121
Tmin = 0.620, Tmax = 0.881l = 2121
10763 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.051P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max = 0.002
S = 0.98Δρmax = 0.93 e Å3
5553 reflectionsΔρmin = 0.64 e Å3
226 parametersAbsolute structure: Flack x determined using 1902 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraintsAbsolute structure parameter: 0.005 (8)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.66284 (4)0.72310 (3)0.72527 (3)0.02040 (12)
Cl10.76060 (14)0.58664 (7)0.76668 (9)0.0313 (2)
N10.4650 (4)0.7138 (2)0.7820 (3)0.0226 (7)
N20.5842 (4)0.8531 (2)0.6986 (2)0.0186 (6)
N30.8353 (4)0.7649 (2)0.6587 (2)0.0216 (7)
C10.3905 (6)0.6378 (3)0.7988 (3)0.0290 (9)
H10.44000.58150.79080.035*
C20.2443 (6)0.6391 (4)0.8275 (4)0.0332 (10)
H20.19250.58420.83810.040*
C30.1725 (6)0.7206 (3)0.8411 (3)0.0315 (10)
H30.07160.72240.86150.038*
C40.2505 (5)0.8002 (3)0.8244 (3)0.0278 (9)
H40.20420.85720.83300.033*
C50.3970 (5)0.7939 (3)0.7948 (3)0.0228 (8)
C60.4969 (5)0.8748 (3)0.7773 (3)0.0223 (8)
H6A0.42530.92750.75840.027*
H6B0.57550.89010.83780.027*
C70.7305 (5)0.9084 (3)0.6999 (3)0.0229 (8)
H7A0.78590.92090.76790.027*
H7B0.70060.96650.66640.027*
C80.8414 (5)0.8552 (3)0.6475 (3)0.0225 (8)
C90.9431 (6)0.8942 (4)0.5936 (4)0.0326 (10)
H90.94770.95790.58780.039*
C101.0386 (6)0.8394 (4)0.5482 (4)0.0377 (12)
H101.10740.86500.50940.045*
C111.0321 (6)0.7478 (4)0.5600 (4)0.0355 (11)
H111.09700.70910.52970.043*
C120.9305 (5)0.7127 (3)0.6163 (3)0.0289 (9)
H120.92800.64920.62520.035*
C130.4719 (5)0.8569 (3)0.6009 (3)0.0227 (8)
H13A0.53100.83570.55080.027*
H13B0.38100.81460.60110.027*
C140.4033 (6)0.9487 (3)0.5723 (3)0.0273 (9)
H140.33640.97630.61100.033*
C150.4322 (7)0.9929 (4)0.4953 (3)0.0401 (12)
H15A0.49880.96660.45570.048*
H15B0.38641.05090.47980.048*
Cl20.41399 (12)0.63022 (7)0.47752 (8)0.0252 (2)
O10.4560 (8)0.5597 (4)0.4223 (3)0.0767 (18)
O20.3144 (10)0.6004 (6)0.5373 (8)0.171 (5)
O30.5608 (8)0.6629 (4)0.5360 (5)0.107 (3)
O40.3369 (4)0.7032 (2)0.4174 (3)0.0319 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0192 (2)0.0176 (2)0.0244 (2)0.0038 (2)0.00465 (16)0.0018 (2)
Cl10.0371 (6)0.0222 (5)0.0361 (6)0.0127 (4)0.0108 (5)0.0074 (4)
N10.0176 (16)0.0248 (18)0.0248 (17)0.0012 (13)0.0028 (13)0.0010 (14)
N20.0159 (14)0.0196 (16)0.0192 (15)0.0014 (12)0.0007 (12)0.0001 (13)
N30.0173 (16)0.0254 (18)0.0209 (17)0.0017 (13)0.0012 (13)0.0017 (13)
C10.029 (2)0.025 (2)0.034 (2)0.0020 (17)0.0077 (18)0.0004 (18)
C20.028 (2)0.036 (3)0.037 (3)0.0057 (19)0.011 (2)0.000 (2)
C30.023 (2)0.046 (3)0.026 (2)0.0020 (19)0.0073 (17)0.002 (2)
C40.0214 (19)0.036 (2)0.025 (2)0.0091 (17)0.0026 (16)0.0045 (17)
C50.023 (2)0.0229 (19)0.0209 (19)0.0036 (15)0.0006 (15)0.0011 (15)
C60.026 (2)0.020 (2)0.0199 (18)0.0064 (16)0.0022 (15)0.0036 (15)
C70.0191 (18)0.0215 (19)0.0253 (19)0.0009 (15)0.0020 (15)0.0014 (15)
C80.0165 (17)0.029 (2)0.0195 (18)0.0016 (15)0.0019 (14)0.0020 (16)
C90.026 (2)0.036 (3)0.034 (2)0.0020 (18)0.0013 (18)0.0131 (19)
C100.020 (2)0.064 (4)0.028 (2)0.003 (2)0.0036 (17)0.008 (2)
C110.026 (2)0.051 (3)0.029 (2)0.003 (2)0.0044 (18)0.000 (2)
C120.021 (2)0.036 (2)0.029 (2)0.0034 (17)0.0042 (17)0.0029 (18)
C130.0229 (19)0.0215 (19)0.0212 (18)0.0027 (15)0.0013 (15)0.0028 (15)
C140.030 (2)0.024 (2)0.024 (2)0.0081 (17)0.0038 (17)0.0019 (16)
C150.060 (4)0.032 (3)0.023 (2)0.003 (2)0.003 (2)0.005 (2)
Cl20.0280 (5)0.0224 (4)0.0248 (4)0.0025 (4)0.0041 (4)0.0011 (3)
O10.113 (4)0.061 (3)0.044 (3)0.041 (3)0.011 (3)0.021 (2)
O20.140 (6)0.137 (6)0.290 (11)0.107 (6)0.169 (8)0.169 (7)
O30.107 (5)0.050 (3)0.122 (5)0.016 (3)0.080 (4)0.016 (3)
O40.0277 (16)0.0264 (16)0.0375 (18)0.0013 (13)0.0033 (14)0.0073 (14)
Geometric parameters (Å, º) top
Cu1—N31.979 (4)C7—C81.520 (6)
Cu1—N11.991 (4)C7—H7A0.9900
Cu1—N22.048 (3)C7—H7B0.9900
Cu1—Cl12.2176 (11)C8—C91.379 (6)
N1—C11.333 (6)C9—C101.386 (8)
N1—C51.346 (5)C9—H90.9500
N2—C61.480 (5)C10—C111.371 (9)
N2—C71.478 (5)C10—H100.9500
N2—C131.498 (5)C11—C121.379 (7)
N3—C121.338 (6)C11—H110.9500
N3—C81.350 (6)C12—H120.9500
C1—C21.372 (7)C13—C141.502 (6)
C1—H10.9500C13—H13A0.9900
C2—C31.382 (7)C13—H13B0.9900
C2—H20.9500C14—C151.326 (7)
C3—C41.393 (7)C14—H140.9500
C3—H30.9500C15—H15A0.9500
C4—C51.382 (6)C15—H15B0.9500
C4—H40.9500Cl2—O21.372 (6)
C5—C61.515 (6)Cl2—O11.388 (5)
C6—H6A0.9900Cl2—O31.423 (5)
C6—H6B0.9900Cl2—O41.443 (3)
N3—Cu1—N1164.53 (15)N2—C7—C8107.4 (3)
N3—Cu1—N281.96 (14)N2—C7—H7A110.2
N1—Cu1—N282.65 (14)C8—C7—H7A110.2
N3—Cu1—Cl198.06 (11)N2—C7—H7B110.2
N1—Cu1—Cl197.42 (11)C8—C7—H7B110.2
N2—Cu1—Cl1174.94 (10)H7A—C7—H7B108.5
C1—N1—C5119.6 (4)N3—C8—C9121.5 (4)
C1—N1—Cu1126.2 (3)N3—C8—C7114.7 (4)
C5—N1—Cu1113.9 (3)C9—C8—C7123.8 (4)
C6—N2—C7114.1 (3)C8—C9—C10119.2 (5)
C6—N2—C13110.8 (3)C8—C9—H9120.4
C7—N2—C13111.2 (3)C10—C9—H9120.4
C6—N2—Cu1105.1 (2)C11—C10—C9119.0 (5)
C7—N2—Cu1106.3 (2)C11—C10—H10120.5
C13—N2—Cu1108.9 (2)C9—C10—H10120.5
C12—N3—C8118.9 (4)C10—C11—C12119.2 (5)
C12—N3—Cu1126.2 (3)C10—C11—H11120.4
C8—N3—Cu1114.5 (3)C12—C11—H11120.4
N1—C1—C2121.5 (4)N3—C12—C11122.2 (5)
N1—C1—H1119.2N3—C12—H12118.9
C2—C1—H1119.2C11—C12—H12118.9
C1—C2—C3119.8 (5)C14—C13—N2114.5 (3)
C1—C2—H2120.1C14—C13—H13A108.6
C3—C2—H2120.1N2—C13—H13A108.6
C2—C3—C4118.9 (4)C14—C13—H13B108.6
C2—C3—H3120.6N2—C13—H13B108.6
C4—C3—H3120.6H13A—C13—H13B107.6
C5—C4—C3118.3 (4)C15—C14—C13122.8 (5)
C5—C4—H4120.9C15—C14—H14118.6
C3—C4—H4120.9C13—C14—H14118.6
N1—C5—C4122.0 (4)C14—C15—H15A120.0
N1—C5—C6114.4 (4)C14—C15—H15B120.0
C4—C5—C6123.6 (4)H15A—C15—H15B120.0
N2—C6—C5108.9 (3)O2—Cl2—O1110.6 (5)
N2—C6—H6A109.9O2—Cl2—O3109.1 (7)
C5—C6—H6A109.9O1—Cl2—O3106.7 (4)
N2—C6—H6B109.9O2—Cl2—O4109.8 (3)
C5—C6—H6B109.9O1—Cl2—O4112.1 (3)
H6A—C6—H6B108.3O3—Cl2—O4108.5 (3)
C5—N1—C1—C21.1 (7)Cu1—N2—C7—C840.9 (3)
Cu1—N1—C1—C2172.3 (4)C12—N3—C8—C90.0 (6)
N1—C1—C2—C31.1 (8)Cu1—N3—C8—C9173.1 (3)
C1—C2—C3—C40.5 (7)C12—N3—C8—C7179.1 (4)
C2—C3—C4—C50.0 (7)Cu1—N3—C8—C77.9 (4)
C1—N1—C5—C40.6 (6)N2—C7—C8—N333.3 (4)
Cu1—N1—C5—C4173.6 (3)N2—C7—C8—C9147.6 (4)
C1—N1—C5—C6177.6 (4)N3—C8—C9—C101.4 (6)
Cu1—N1—C5—C68.2 (4)C7—C8—C9—C10179.6 (4)
C3—C4—C5—N10.1 (6)C8—C9—C10—C111.6 (7)
C3—C4—C5—C6178.0 (4)C9—C10—C11—C120.3 (7)
C7—N2—C6—C5157.0 (3)C8—N3—C12—C111.3 (6)
C13—N2—C6—C576.5 (4)Cu1—N3—C12—C11170.8 (3)
Cu1—N2—C6—C540.9 (3)C10—C11—C12—N31.2 (7)
N1—C5—C6—N234.0 (5)C6—N2—C13—C1464.3 (5)
C4—C5—C6—N2147.9 (4)C7—N2—C13—C1463.7 (5)
C6—N2—C7—C8156.3 (3)Cu1—N2—C13—C14179.4 (3)
C13—N2—C7—C877.5 (4)N2—C13—C14—C15117.2 (5)
(5) Di-µ-chlorido-bis({(prop-2-en-1-yl)bis[pyridin-2-yl)methylidene]amine-κ3N,N',N''}copper(II)) bis(tetraphenylborate) top
Crystal data top
[Cu2Cl2(C15H17N3)2](C24H20B)2F(000) = 1372
Mr = 1315.05Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.3914 (2) ÅCell parameters from 9988 reflections
b = 12.2672 (3) Åθ = 2.6–26.7°
c = 26.0083 (6) ŵ = 0.77 mm1
β = 91.485 (1)°T = 150 K
V = 3314.25 (13) Å3Rhomboid, blue
Z = 20.52 × 0.22 × 0.21 mm
Data collection top
Bruker SMART APEXII
diffractometer
7079 independent reflections
Radiation source: fine-focus sealed tube6006 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.33 pixels mm-1θmax = 26.8°, θmin = 1.6°
φ and ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1515
Tmin = 0.691, Tmax = 0.853l = 3232
42327 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.048P)2 + 1.3734P]
where P = (Fo2 + 2Fc2)/3
7079 reflections(Δ/σ)max = 0.001
425 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.33 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. Disorder in the terminal ethylinic group was observed. C14 and C15 were modeled over two sites, rotated by approximately 180°. The two sites were refined with occupancies summed to unity yielding a 0.738:0.262 ratio. All atoms were refined with anisotropic displacement parameters and the pairs of atoms restrained to have similar displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.58967 (2)0.96826 (2)0.05495 (2)0.02885 (8)
Cl10.34988 (4)0.93929 (4)0.01632 (2)0.03497 (11)
N10.65150 (13)0.82020 (13)0.03516 (5)0.0312 (3)
N20.56575 (14)0.89354 (13)0.12426 (5)0.0299 (3)
N30.53381 (13)1.09774 (13)0.09560 (5)0.0302 (3)
C10.72573 (17)0.79565 (17)0.00488 (7)0.0371 (4)
H10.74250.85060.02950.045*
C20.77808 (19)0.69374 (19)0.01133 (8)0.0440 (5)
H20.82950.67850.04010.053*
C30.7549 (2)0.61374 (19)0.02473 (8)0.0458 (5)
H30.79090.54300.02120.055*
C40.67835 (19)0.63819 (17)0.06611 (8)0.0414 (4)
H40.66080.58440.09130.050*
C50.62796 (17)0.74222 (16)0.07010 (7)0.0333 (4)
C60.54168 (19)0.77695 (16)0.11276 (7)0.0370 (4)
H6A0.45040.76620.10210.044*
H6B0.55980.73240.14380.044*
C70.45336 (17)0.94942 (16)0.14641 (7)0.0331 (4)
H7A0.44840.93300.18360.040*
H7B0.37270.92460.12900.040*
C80.47144 (16)1.06948 (16)0.13837 (6)0.0305 (4)
C90.42605 (17)1.14717 (17)0.17211 (7)0.0359 (4)
H90.38071.12580.20170.043*
C100.44771 (19)1.25541 (18)0.16205 (7)0.0413 (5)
H100.41791.30990.18480.050*
C110.5132 (2)1.28447 (17)0.11852 (8)0.0433 (5)
H110.52981.35900.11120.052*
C120.55404 (18)1.20365 (16)0.08596 (7)0.0372 (4)
H120.59791.22360.05580.045*
C130.68103 (18)0.90759 (19)0.16005 (7)0.0419 (5)
H13A0.68790.84370.18320.050*0.738 (10)
H13B0.66870.97320.18150.050*0.738 (10)
H13C0.69900.98650.16350.050*0.262 (10)
H13D0.65810.88030.19440.050*0.262 (10)
C140.8046 (3)0.9192 (4)0.13113 (12)0.0387 (10)0.738 (10)
H140.81490.98150.10990.046*0.738 (10)
C150.8975 (4)0.8485 (5)0.13370 (18)0.0578 (12)0.738 (10)
H15A0.88980.78540.15460.069*0.738 (10)
H15B0.97320.85980.11470.069*0.738 (10)
C14A0.8025 (8)0.8517 (11)0.1445 (3)0.038 (3)0.262 (10)
H14A0.81080.77460.14420.046*0.262 (10)
C15A0.8925 (14)0.9139 (16)0.1319 (5)0.067 (4)0.262 (10)
H15C0.88090.99060.13270.080*0.262 (10)
H15D0.97220.88400.12160.080*0.262 (10)
B10.04320 (18)0.40952 (16)0.16838 (7)0.0262 (4)
C160.13424 (15)0.37492 (14)0.21864 (6)0.0262 (3)
C170.11036 (19)0.27900 (15)0.24593 (7)0.0350 (4)
H170.03850.23560.23560.042*
C180.1870 (2)0.24432 (17)0.28740 (7)0.0463 (5)
H180.16780.17790.30440.056*
C190.2912 (2)0.3065 (2)0.30394 (7)0.0507 (6)
H190.34580.28210.33150.061*
C200.31481 (18)0.4043 (2)0.27997 (7)0.0450 (5)
H200.38390.44920.29180.054*
C210.23715 (17)0.43764 (16)0.23815 (6)0.0326 (4)
H210.25490.50560.22230.039*
C220.01424 (15)0.30275 (15)0.13123 (6)0.0277 (4)
C230.08903 (17)0.20775 (15)0.13197 (7)0.0329 (4)
H230.15650.20170.15720.039*
C240.0696 (2)0.12159 (17)0.09762 (7)0.0409 (4)
H240.12260.05860.09990.049*
C250.0272 (2)0.12823 (18)0.06021 (7)0.0431 (5)
H250.04140.07010.03660.052*
C260.10279 (18)0.22065 (18)0.05772 (7)0.0394 (5)
H260.16940.22620.03210.047*
C270.08229 (17)0.30590 (17)0.09238 (6)0.0334 (4)
H270.13570.36860.08970.040*
C280.08922 (16)0.46261 (14)0.19156 (6)0.0278 (4)
C290.20598 (17)0.40643 (17)0.19516 (7)0.0352 (4)
H290.21180.33410.18230.042*
C300.31405 (19)0.45312 (19)0.21704 (8)0.0444 (5)
H300.39150.41230.21890.053*
C310.3093 (2)0.55789 (19)0.23598 (8)0.0472 (5)
H310.38330.59000.25040.057*
C320.1952 (2)0.61582 (17)0.23374 (8)0.0436 (5)
H320.19030.68790.24700.052*
C330.08759 (19)0.56819 (16)0.21206 (7)0.0348 (4)
H330.01000.60900.21120.042*
C340.11517 (16)0.49713 (15)0.13066 (6)0.0280 (3)
C350.05047 (19)0.58030 (17)0.10391 (7)0.0373 (4)
H350.03860.59080.10970.045*
C360.1107 (2)0.64867 (18)0.06903 (8)0.0460 (5)
H360.06260.70390.05160.055*
C370.2401 (2)0.63630 (17)0.05979 (7)0.0425 (5)
H370.28210.68350.03660.051*
C380.30705 (19)0.55453 (17)0.08469 (7)0.0394 (4)
H380.39600.54460.07850.047*
C390.24534 (18)0.48612 (16)0.11897 (7)0.0334 (4)
H390.29370.42940.13520.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03074 (12)0.03593 (14)0.02021 (11)0.00552 (9)0.00718 (8)0.00348 (8)
Cl10.0353 (2)0.0452 (3)0.0245 (2)0.00992 (19)0.00390 (16)0.00040 (17)
N10.0281 (7)0.0408 (9)0.0249 (7)0.0026 (6)0.0038 (5)0.0060 (6)
N20.0321 (7)0.0373 (9)0.0207 (6)0.0006 (6)0.0049 (5)0.0027 (6)
N30.0290 (7)0.0365 (9)0.0251 (7)0.0038 (6)0.0034 (5)0.0035 (6)
C10.0338 (9)0.0502 (12)0.0277 (8)0.0009 (8)0.0068 (7)0.0072 (8)
C20.0393 (10)0.0574 (14)0.0359 (10)0.0034 (10)0.0083 (8)0.0122 (9)
C30.0426 (11)0.0461 (12)0.0487 (12)0.0066 (9)0.0023 (9)0.0132 (10)
C40.0421 (10)0.0402 (11)0.0420 (10)0.0008 (9)0.0026 (8)0.0031 (9)
C50.0309 (9)0.0393 (11)0.0299 (9)0.0020 (8)0.0020 (7)0.0054 (8)
C60.0423 (10)0.0375 (11)0.0318 (9)0.0024 (8)0.0106 (8)0.0012 (8)
C70.0342 (9)0.0431 (11)0.0224 (8)0.0011 (8)0.0099 (7)0.0001 (7)
C80.0291 (8)0.0414 (10)0.0209 (7)0.0012 (7)0.0003 (6)0.0017 (7)
C90.0349 (9)0.0478 (12)0.0251 (8)0.0086 (8)0.0022 (7)0.0027 (8)
C100.0402 (10)0.0463 (12)0.0374 (10)0.0105 (9)0.0008 (8)0.0105 (9)
C110.0460 (11)0.0346 (11)0.0492 (11)0.0002 (9)0.0012 (9)0.0047 (9)
C120.0368 (9)0.0404 (11)0.0346 (9)0.0060 (8)0.0054 (7)0.0021 (8)
C130.0401 (10)0.0563 (13)0.0289 (9)0.0066 (9)0.0048 (8)0.0070 (9)
C140.0368 (19)0.043 (2)0.0360 (14)0.0077 (14)0.0060 (11)0.0073 (14)
C150.039 (2)0.063 (3)0.072 (2)0.002 (2)0.0006 (16)0.012 (2)
C14A0.037 (5)0.044 (7)0.033 (4)0.005 (4)0.003 (3)0.001 (4)
C15A0.043 (7)0.072 (10)0.085 (8)0.005 (7)0.002 (5)0.007 (8)
B10.0282 (9)0.0284 (10)0.0222 (8)0.0008 (8)0.0023 (7)0.0014 (7)
C160.0285 (8)0.0280 (9)0.0221 (7)0.0032 (7)0.0048 (6)0.0009 (6)
C170.0504 (11)0.0290 (10)0.0260 (8)0.0003 (8)0.0073 (7)0.0001 (7)
C180.0760 (15)0.0366 (11)0.0270 (9)0.0242 (11)0.0126 (9)0.0059 (8)
C190.0504 (12)0.0747 (17)0.0267 (9)0.0310 (12)0.0003 (8)0.0015 (10)
C200.0305 (9)0.0762 (16)0.0282 (9)0.0044 (10)0.0000 (7)0.0080 (10)
C210.0322 (9)0.0410 (10)0.0247 (8)0.0013 (8)0.0042 (7)0.0015 (7)
C220.0271 (8)0.0341 (10)0.0223 (7)0.0049 (7)0.0056 (6)0.0001 (7)
C230.0344 (9)0.0364 (10)0.0279 (8)0.0013 (8)0.0034 (7)0.0033 (7)
C240.0497 (11)0.0360 (11)0.0375 (10)0.0006 (9)0.0111 (8)0.0062 (8)
C250.0528 (12)0.0467 (12)0.0304 (9)0.0147 (10)0.0105 (8)0.0116 (8)
C260.0381 (10)0.0567 (13)0.0236 (8)0.0133 (9)0.0018 (7)0.0037 (8)
C270.0320 (9)0.0420 (11)0.0262 (8)0.0024 (8)0.0038 (7)0.0001 (8)
C280.0316 (8)0.0311 (9)0.0208 (7)0.0036 (7)0.0013 (6)0.0033 (7)
C290.0335 (9)0.0404 (11)0.0319 (9)0.0011 (8)0.0046 (7)0.0025 (8)
C300.0311 (10)0.0620 (14)0.0404 (11)0.0027 (9)0.0042 (8)0.0041 (10)
C310.0430 (11)0.0592 (14)0.0398 (11)0.0219 (10)0.0061 (9)0.0003 (10)
C320.0596 (13)0.0363 (11)0.0349 (10)0.0142 (10)0.0048 (9)0.0003 (8)
C330.0420 (10)0.0328 (10)0.0298 (9)0.0015 (8)0.0029 (7)0.0010 (7)
C340.0329 (9)0.0300 (9)0.0209 (7)0.0029 (7)0.0003 (6)0.0002 (7)
C350.0388 (10)0.0434 (11)0.0299 (9)0.0016 (9)0.0030 (7)0.0079 (8)
C360.0589 (13)0.0457 (12)0.0336 (10)0.0047 (10)0.0030 (9)0.0161 (9)
C370.0534 (12)0.0430 (12)0.0312 (9)0.0118 (9)0.0047 (8)0.0100 (8)
C380.0358 (10)0.0511 (12)0.0315 (9)0.0092 (9)0.0053 (7)0.0041 (8)
C390.0352 (9)0.0361 (10)0.0289 (8)0.0008 (8)0.0039 (7)0.0053 (7)
Geometric parameters (Å, º) top
Cu1—N11.9984 (16)B1—C341.648 (2)
Cu1—N32.0024 (15)B1—C161.649 (2)
Cu1—N22.0431 (14)B1—C281.650 (2)
Cu1—Cl1i2.2754 (5)B1—C221.650 (3)
Cu1—Cl12.6861 (5)C16—C171.400 (2)
Cl1—Cu1i2.2754 (5)C16—C211.402 (2)
N1—C11.346 (2)C17—C181.391 (3)
N1—C51.346 (2)C17—H170.9500
N2—C61.481 (2)C18—C191.384 (3)
N2—C71.483 (2)C18—H180.9500
N2—C131.508 (2)C19—C201.377 (3)
N3—C121.341 (2)C19—H190.9500
N3—C81.347 (2)C20—C211.398 (3)
C1—C21.375 (3)C20—H200.9500
C1—H10.9500C21—H210.9500
C2—C31.383 (3)C22—C231.401 (3)
C2—H20.9500C22—C271.406 (2)
C3—C41.387 (3)C23—C241.395 (3)
C3—H30.9500C23—H230.9500
C4—C51.384 (3)C24—C251.383 (3)
C4—H40.9500C24—H240.9500
C5—C61.506 (2)C25—C261.380 (3)
C6—H6A0.9900C25—H250.9500
C6—H6B0.9900C26—C271.393 (3)
C7—C81.500 (3)C26—H260.9500
C7—H7A0.9900C27—H270.9500
C7—H7B0.9900C28—C331.401 (3)
C8—C91.386 (3)C28—C291.401 (2)
C9—C101.373 (3)C29—C301.395 (3)
C9—H90.9500C29—H290.9500
C10—C111.383 (3)C30—C311.377 (3)
C10—H100.9500C30—H300.9500
C11—C121.378 (3)C31—C321.385 (3)
C11—H110.9500C31—H310.9500
C12—H120.9500C32—C331.394 (3)
C13—C14A1.501 (9)C32—H320.9500
C13—C141.512 (4)C33—H330.9500
C13—H13A0.9900C34—C351.398 (3)
C13—H13B0.9900C34—C391.401 (2)
C13—H13C0.9900C35—C361.396 (3)
C13—H13D0.9900C35—H350.9500
C14—C151.298 (8)C36—C371.380 (3)
C14—H140.9500C36—H360.9500
C15—H15A0.9500C37—C381.373 (3)
C15—H15B0.9500C37—H370.9500
C14A—C15A1.26 (2)C38—C391.393 (3)
C14A—H14A0.9500C38—H380.9500
C15A—H15C0.9500C39—H390.9500
C15A—H15D0.9500
N1—Cu1—N3163.03 (6)C15A—C14A—H14A122.3
N1—Cu1—N282.34 (6)C13—C14A—H14A122.3
N3—Cu1—N281.17 (6)C14A—C15A—H15C120.0
N1—Cu1—Cl1i98.38 (4)C14A—C15A—H15D120.0
N3—Cu1—Cl1i97.16 (4)H15C—C15A—H15D120.0
N2—Cu1—Cl1i170.01 (4)C34—B1—C16112.33 (14)
N1—Cu1—Cl194.86 (4)C34—B1—C28110.84 (14)
N3—Cu1—Cl191.36 (4)C16—B1—C28106.17 (13)
N2—Cu1—Cl197.92 (4)C34—B1—C22104.35 (13)
Cl1i—Cu1—Cl191.960 (15)C16—B1—C22110.60 (14)
Cu1i—Cl1—Cu188.041 (15)C28—B1—C22112.70 (14)
C1—N1—C5118.75 (17)C17—C16—C21114.94 (16)
C1—N1—Cu1126.67 (14)C17—C16—B1120.84 (15)
C5—N1—Cu1114.00 (11)C21—C16—B1124.20 (15)
C6—N2—C7113.21 (14)C18—C17—C16123.01 (19)
C6—N2—C13111.24 (15)C18—C17—H17118.5
C7—N2—C13109.16 (13)C16—C17—H17118.5
C6—N2—Cu1106.20 (10)C19—C18—C17120.0 (2)
C7—N2—Cu1104.50 (11)C19—C18—H18120.0
C13—N2—Cu1112.37 (11)C17—C18—H18120.0
C12—N3—C8119.01 (16)C20—C19—C18119.11 (18)
C12—N3—Cu1128.37 (12)C20—C19—H19120.4
C8—N3—Cu1112.59 (12)C18—C19—H19120.4
N1—C1—C2122.28 (19)C19—C20—C21120.1 (2)
N1—C1—H1118.9C19—C20—H20120.0
C2—C1—H1118.9C21—C20—H20120.0
C1—C2—C3119.07 (18)C20—C21—C16122.72 (19)
C1—C2—H2120.5C20—C21—H21118.6
C3—C2—H2120.5C16—C21—H21118.6
C2—C3—C4119.1 (2)C23—C22—C27114.71 (16)
C2—C3—H3120.5C23—C22—B1124.03 (15)
C4—C3—H3120.5C27—C22—B1120.98 (16)
C5—C4—C3118.9 (2)C24—C23—C22123.39 (17)
C5—C4—H4120.6C24—C23—H23118.3
C3—C4—H4120.6C22—C23—H23118.3
N1—C5—C4121.93 (17)C25—C24—C23119.76 (19)
N1—C5—C6114.73 (16)C25—C24—H24120.1
C4—C5—C6123.34 (18)C23—C24—H24120.1
N2—C6—C5108.74 (15)C26—C25—C24118.94 (18)
N2—C6—H6A109.9C26—C25—H25120.5
C5—C6—H6A109.9C24—C25—H25120.5
N2—C6—H6B109.9C25—C26—C27120.60 (18)
C5—C6—H6B109.9C25—C26—H26119.7
H6A—C6—H6B108.3C27—C26—H26119.7
N2—C7—C8107.27 (14)C26—C27—C22122.59 (18)
N2—C7—H7A110.3C26—C27—H27118.7
C8—C7—H7A110.3C22—C27—H27118.7
N2—C7—H7B110.3C33—C28—C29115.56 (16)
C8—C7—H7B110.3C33—C28—B1120.13 (15)
H7A—C7—H7B108.5C29—C28—B1124.20 (16)
N3—C8—C9121.64 (18)C30—C29—C28122.22 (19)
N3—C8—C7115.62 (15)C30—C29—H29118.9
C9—C8—C7122.74 (16)C28—C29—H29118.9
C10—C9—C8118.95 (18)C31—C30—C29120.5 (2)
C10—C9—H9120.5C31—C30—H30119.8
C8—C9—H9120.5C29—C30—H30119.8
C9—C10—C11119.47 (18)C30—C31—C32119.13 (19)
C9—C10—H10120.3C30—C31—H31120.4
C11—C10—H10120.3C32—C31—H31120.4
C12—C11—C10118.9 (2)C31—C32—C33119.9 (2)
C12—C11—H11120.5C31—C32—H32120.0
C10—C11—H11120.5C33—C32—H32120.0
N3—C12—C11121.99 (18)C32—C33—C28122.66 (19)
N3—C12—H12119.0C32—C33—H33118.7
C11—C12—H12119.0C28—C33—H33118.7
C14A—C13—N2116.2 (3)C35—C34—C39114.66 (16)
N2—C13—C14112.03 (17)C35—C34—B1123.55 (15)
N2—C13—H13A109.2C39—C34—B1121.48 (16)
C14—C13—H13A109.2C36—C35—C34122.96 (18)
N2—C13—H13B109.2C36—C35—H35118.5
C14—C13—H13B109.2C34—C35—H35118.5
H13A—C13—H13B107.9C37—C36—C35120.17 (19)
C14A—C13—H13C108.2C37—C36—H36119.9
N2—C13—H13C108.2C35—C36—H36119.9
C14A—C13—H13D108.2C38—C37—C36118.82 (18)
N2—C13—H13D108.2C38—C37—H37120.6
H13C—C13—H13D107.4C36—C37—H37120.6
C15—C14—C13123.5 (5)C37—C38—C39120.39 (18)
C15—C14—H14118.3C37—C38—H38119.8
C13—C14—H14118.3C39—C38—H38119.8
C14—C15—H15A120.0C38—C39—C34122.96 (18)
C14—C15—H15B120.0C38—C39—H39118.5
H15A—C15—H15B120.0C34—C39—H39118.5
C15A—C14A—C13115.5 (15)
C5—N1—C1—C20.1 (3)C16—C17—C18—C191.1 (3)
Cu1—N1—C1—C2170.78 (14)C17—C18—C19—C202.2 (3)
N1—C1—C2—C30.6 (3)C18—C19—C20—C212.6 (3)
C1—C2—C3—C40.7 (3)C19—C20—C21—C160.3 (3)
C2—C3—C4—C50.3 (3)C17—C16—C21—C203.4 (3)
C1—N1—C5—C40.4 (3)B1—C16—C21—C20178.08 (16)
Cu1—N1—C5—C4171.48 (14)C34—B1—C22—C23100.91 (18)
C1—N1—C5—C6178.74 (16)C16—B1—C22—C2320.1 (2)
Cu1—N1—C5—C69.42 (19)C28—B1—C22—C23138.76 (16)
C3—C4—C5—N10.3 (3)C34—B1—C22—C2772.70 (18)
C3—C4—C5—C6178.75 (18)C16—B1—C22—C27166.29 (14)
C7—N2—C6—C5153.66 (15)C28—B1—C22—C2747.6 (2)
C13—N2—C6—C582.99 (17)C27—C22—C23—C240.8 (3)
Cu1—N2—C6—C539.56 (17)B1—C22—C23—C24174.80 (16)
N1—C5—C6—N233.5 (2)C22—C23—C24—C250.5 (3)
C4—C5—C6—N2147.40 (18)C23—C24—C25—C260.0 (3)
C6—N2—C7—C8159.88 (14)C24—C25—C26—C270.2 (3)
C13—N2—C7—C875.62 (18)C25—C26—C27—C220.2 (3)
Cu1—N2—C7—C844.77 (15)C23—C22—C27—C260.7 (2)
C12—N3—C8—C91.0 (3)B1—C22—C27—C26174.85 (16)
Cu1—N3—C8—C9179.30 (13)C34—B1—C28—C3346.5 (2)
C12—N3—C8—C7179.71 (15)C16—B1—C28—C3375.74 (19)
Cu1—N3—C8—C71.45 (19)C22—B1—C28—C33163.04 (15)
N2—C7—C8—N331.9 (2)C34—B1—C28—C29137.32 (17)
N2—C7—C8—C9148.81 (16)C16—B1—C28—C29100.43 (18)
N3—C8—C9—C101.3 (3)C22—B1—C28—C2920.8 (2)
C7—C8—C9—C10179.47 (17)C33—C28—C29—C300.9 (3)
C8—C9—C10—C110.5 (3)B1—C28—C29—C30177.23 (17)
C9—C10—C11—C120.7 (3)C28—C29—C30—C310.2 (3)
C8—N3—C12—C110.1 (3)C29—C30—C31—C321.0 (3)
Cu1—N3—C12—C11177.82 (14)C30—C31—C32—C330.6 (3)
C10—C11—C12—N31.0 (3)C31—C32—C33—C280.6 (3)
C6—N2—C13—C14A51.9 (6)C29—C28—C33—C321.3 (3)
C7—N2—C13—C14A177.5 (6)B1—C28—C33—C32177.77 (16)
Cu1—N2—C13—C14A67.0 (6)C16—B1—C34—C35144.98 (17)
C6—N2—C13—C1489.7 (3)C28—B1—C34—C3526.4 (2)
C7—N2—C13—C14144.7 (2)C22—B1—C34—C3595.18 (19)
Cu1—N2—C13—C1429.2 (3)C16—B1—C34—C3941.8 (2)
N2—C13—C14—C15115.0 (3)C28—B1—C34—C39160.34 (16)
N2—C13—C14A—C15A112.0 (9)C22—B1—C34—C3978.09 (19)
C34—B1—C16—C17159.66 (15)C39—C34—C35—C361.2 (3)
C28—B1—C16—C1779.05 (19)B1—C34—C35—C36174.91 (18)
C22—B1—C16—C1743.5 (2)C34—C35—C36—C370.3 (3)
C34—B1—C16—C2121.9 (2)C35—C36—C37—C381.3 (3)
C28—B1—C16—C2199.42 (18)C36—C37—C38—C390.6 (3)
C22—B1—C16—C21138.02 (16)C37—C38—C39—C341.1 (3)
C21—C16—C17—C183.7 (3)C35—C34—C39—C382.0 (3)
B1—C16—C17—C18177.65 (16)B1—C34—C39—C38175.79 (17)
Symmetry code: (i) x+1, y+2, z.
 

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