Download citation
Download citation
link to html
A novel pyrazolylpyrimidine ligand (L) and its complex CuLCl2 were prepared and structurally characterized. The simultaneous crystallization of three polymorphs of CuLCl2, green (G), emerald green (EG) and orange (O), was discovered. The molecular structures vary only slightly between the three forms. The Cu atom forms four coordinate bonds with the two N and two Cl atoms, and a shortened Cu...H contact with an H atom of the phenyl ring in L. The structural difference between polymorphs was analyzed with the boundary surfaces of molecular Voronoi–Dirichlet polyhedra. The difference in colour of the polymorphs is likely to be due to the different π–π stackings. There is no stacking in the G modification, but EG and O polymorphs demonstrate face-to-face and slipped stacking, resulting in dimers and infinite chains, respectively. The EG and O polymorphs are packed according to the hexagonal close-packing motif, while in G no special topology is found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810403294X/av5023sup1.cif
Contains datablocks 1, 2g, 2eg, 2o, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810403294X/av50231sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810403294X/av50232gsup3.hkl
Contains datablock 2g

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810403294X/av50232egsup4.hkl
Contains datablock 2eg

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810403294X/av50232osup5.hkl
Contains datablock 2o

CCDC references: 268157; 268158; 268159; 268160

Computing details top

For all compounds, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL, TOPOS 4.0 Standard; software used to prepare material for publication: local programs.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(1) 4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenyl-pyrimidyne top
Crystal data top
C16H16N4Dx = 1.245 Mg m3
Mr = 264.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 1009 reflections
a = 19.499 (3) Åθ = 2.5–22.1°
b = 4.7884 (6) ŵ = 0.08 mm1
c = 15.106 (2) ÅT = 293 K
V = 1410.5 (4) Å3Lath, colourless
Z = 40.59 × 0.05 × 0.03 mm
F(000) = 560
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.083
Graphite monochromatorθmax = 30.6°, θmin = 2.5°
Detector resolution: 25 pixels mm-1h = 2727
π–scansk = 36
9460 measured reflectionsl = 2121
2221 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.0847P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
2221 reflectionsΔρmax = 0.14 e Å3
182 parametersΔρmin = 0.15 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (10)
Crystal data top
C16H16N4V = 1410.5 (4) Å3
Mr = 264.33Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 19.499 (3) ŵ = 0.08 mm1
b = 4.7884 (6) ÅT = 293 K
c = 15.106 (2) Å0.59 × 0.05 × 0.03 mm
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
885 reflections with I > 2σ(I)
9460 measured reflectionsRint = 0.083
2221 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.181Δρmax = 0.14 e Å3
S = 0.91Δρmin = 0.15 e Å3
2221 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
182 parametersAbsolute structure parameter: 0 (10)
1 restraint
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C30.8529 (2)0.3636 (9)0.3520 (3)0.0799 (12)
C40.9130 (2)0.3220 (9)0.4000 (3)0.0791 (11)
H4A0.92490.41030.45270.095*
C50.9513 (2)0.1272 (8)0.3556 (3)0.0727 (11)
C60.9255 (2)0.1327 (8)0.2136 (3)0.0625 (9)
C70.8773 (2)0.1804 (8)0.1472 (3)0.0716 (11)
H7A0.83560.08660.14550.086*
C80.8955 (2)0.3770 (9)0.0833 (3)0.0703 (11)
C90.9980 (2)0.4456 (8)0.1520 (3)0.0642 (10)
C101.0663 (2)0.5856 (8)0.1551 (3)0.0678 (10)
C111.0834 (3)0.7937 (9)0.0965 (3)0.0792 (12)
H11A1.05130.85540.05550.095*
C121.1484 (3)0.9130 (10)0.0981 (4)0.0869 (13)
H12A1.15941.05170.05730.104*
C131.1961 (2)0.8301 (10)0.1581 (4)0.0878 (14)
H13A1.23960.91010.15860.105*
C141.1788 (2)0.6243 (11)0.2185 (4)0.0919 (14)
H14A1.21080.56740.26060.110*
C151.1147 (2)0.5032 (9)0.2169 (3)0.0799 (12)
H15A1.10390.36450.25760.096*
C310.7947 (3)0.5540 (10)0.3735 (4)0.1005 (16)
H31A0.79760.60930.43440.121*
H31B0.79700.71650.33640.121*
H31C0.75210.45860.36340.19 (3)*
C511.0191 (2)0.0068 (11)0.3793 (4)0.0902 (13)
H51A1.03460.08660.43400.135*
H51B1.01490.19190.38580.135*
H51C1.05160.04770.33330.135*
C810.8477 (2)0.4494 (12)0.0097 (3)0.0950 (15)
H81A0.80630.34290.01560.143*
H81B0.86910.40700.04590.143*
H81C0.83710.64500.01220.143*
N10.85223 (17)0.2084 (7)0.2793 (2)0.0753 (9)
N20.91272 (17)0.0615 (7)0.2823 (2)0.0690 (9)
N30.95636 (17)0.5093 (7)0.0857 (2)0.0681 (9)
N40.98480 (16)0.2599 (7)0.2170 (2)0.0680 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.102 (3)0.059 (2)0.079 (3)0.011 (2)0.009 (3)0.010 (2)
C40.104 (3)0.064 (2)0.070 (2)0.020 (2)0.007 (3)0.001 (2)
C50.088 (3)0.071 (2)0.059 (2)0.024 (2)0.003 (2)0.006 (2)
C60.072 (2)0.061 (2)0.055 (2)0.0179 (19)0.001 (2)0.0049 (18)
C70.077 (3)0.072 (3)0.066 (3)0.0113 (19)0.003 (2)0.008 (2)
C80.078 (3)0.077 (2)0.055 (2)0.019 (2)0.003 (2)0.008 (2)
C90.080 (2)0.062 (2)0.051 (2)0.0166 (19)0.001 (2)0.0078 (19)
C100.077 (3)0.064 (2)0.063 (2)0.010 (2)0.002 (2)0.014 (2)
C110.096 (3)0.074 (3)0.068 (3)0.009 (2)0.008 (2)0.005 (2)
C120.091 (3)0.083 (3)0.086 (3)0.006 (3)0.001 (3)0.004 (3)
C130.085 (3)0.084 (3)0.095 (4)0.008 (2)0.003 (3)0.008 (3)
C140.082 (3)0.099 (3)0.095 (3)0.008 (3)0.013 (3)0.001 (3)
C150.081 (3)0.079 (3)0.081 (3)0.005 (2)0.008 (2)0.002 (3)
C310.124 (4)0.068 (3)0.109 (4)0.004 (3)0.028 (3)0.000 (3)
C510.091 (3)0.102 (3)0.077 (3)0.017 (3)0.011 (3)0.003 (2)
C810.087 (3)0.125 (4)0.073 (3)0.023 (3)0.016 (2)0.010 (3)
N10.084 (2)0.066 (2)0.076 (2)0.0082 (18)0.0038 (19)0.0034 (19)
N20.077 (2)0.0668 (19)0.0629 (19)0.0123 (17)0.0027 (17)0.0018 (16)
N30.070 (2)0.075 (2)0.0599 (18)0.0111 (17)0.0056 (17)0.0028 (17)
N40.072 (2)0.0695 (19)0.0620 (19)0.0135 (16)0.0039 (18)0.0071 (19)
Geometric parameters (Å, º) top
C3—N11.325 (6)C11—C121.391 (7)
C3—C41.393 (6)C11—H11A0.9300
C3—C311.491 (7)C12—C131.358 (7)
C4—C51.371 (6)C12—H12A0.9300
C4—H4A0.9300C13—C141.386 (7)
C5—N21.376 (5)C13—H13A0.9300
C5—C511.485 (6)C14—C151.378 (6)
C6—N41.309 (5)C14—H14A0.9300
C6—C71.393 (6)C15—H15A0.9300
C6—N21.415 (5)C31—H31A0.9600
C7—C81.394 (6)C31—H31B0.9600
C7—H7A0.9300C31—H31C0.9600
C8—N31.347 (5)C51—H51A0.9600
C8—C811.490 (6)C51—H51B0.9600
C9—N31.325 (5)C51—H51C0.9600
C9—N41.349 (5)C81—H81A0.9600
C9—C101.491 (6)C81—H81B0.9600
C10—C111.374 (6)C81—H81C0.9600
C10—C151.385 (6)N1—N21.374 (5)
N1—C3—C4111.1 (4)C14—C13—H13A120.6
N1—C3—C31121.0 (5)C15—C14—C13120.5 (5)
C4—C3—C31127.9 (5)C15—C14—H14A119.7
C5—C4—C3107.5 (5)C13—C14—H14A119.7
C5—C4—H4A126.2C14—C15—C10120.8 (5)
C3—C4—H4A126.2C14—C15—H15A119.6
C4—C5—N2104.6 (4)C10—C15—H15A119.6
C4—C5—C51129.2 (4)C3—C31—H31A109.5
N2—C5—C51126.3 (4)C3—C31—H31B109.5
N4—C6—C7123.2 (4)H31A—C31—H31B109.5
N4—C6—N2115.6 (4)C3—C31—H31C109.5
C7—C6—N2121.2 (4)H31A—C31—H31C109.5
C6—C7—C8116.0 (4)H31B—C31—H31C109.5
C6—C7—H7A122.0C5—C51—H51A109.5
C8—C7—H7A122.0C5—C51—H51B109.5
N3—C8—C7121.5 (4)H51A—C51—H51B109.5
N3—C8—C81117.5 (4)C5—C51—H51C109.5
C7—C8—C81121.0 (4)H51A—C51—H51C109.5
N3—C9—N4125.8 (4)H51B—C51—H51C109.5
N3—C9—C10117.8 (4)C8—C81—H81A109.5
N4—C9—C10116.3 (3)C8—C81—H81B109.5
C11—C10—C15118.3 (4)H81A—C81—H81B109.5
C11—C10—C9121.5 (4)C8—C81—H81C109.5
C15—C10—C9120.1 (4)H81A—C81—H81C109.5
C10—C11—C12120.6 (4)H81B—C81—H81C109.5
C10—C11—H11A119.7C3—N1—N2104.6 (4)
C12—C11—H11A119.7N1—N2—C5112.3 (3)
C13—C12—C11121.0 (5)N1—N2—C6117.6 (3)
C13—C12—H12A119.5C5—N2—C6130.1 (4)
C11—C12—H12A119.5C9—N3—C8116.9 (4)
C12—C13—C14118.8 (4)C6—N4—C9116.6 (3)
C12—C13—H13A120.6
N1—N2—C6—N4177.4 (3)N4—C9—C10—C156.4 (5)
(2g) (4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenyl-pyrimidyne)dichlorocopper(II) green form top
Crystal data top
C16H16Cl2CuN4F(000) = 812
Mr = 398.77Dx = 1.568 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.2156 (3) ÅCell parameters from 3896 reflections
b = 11.6522 (4) Åθ = 2.7–30.1°
c = 20.3956 (8) ŵ = 1.61 mm1
β = 99.841 (1)°T = 293 K
V = 1689.58 (11) Å3Plate, clear green
Z = 40.54 × 0.23 × 0.04 mm
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
5033 independent reflections
Radiation source: fine-focus sealed tube3781 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 25 pixels mm-1θmax = 32.5°, θmin = 2.7°
π–scansh = 109
Absorption correction: empirical (using intensity measurements)
SADABS (Bruker)
k = 1016
Tmin = 0.645, Tmax = 0.941l = 3029
10578 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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.6674P]
where P = (Fo2 + 2Fc2)/3
5033 reflections(Δ/σ)max = 0.002
208 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C16H16Cl2CuN4V = 1689.58 (11) Å3
Mr = 398.77Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.2156 (3) ŵ = 1.61 mm1
b = 11.6522 (4) ÅT = 293 K
c = 20.3956 (8) Å0.54 × 0.23 × 0.04 mm
β = 99.841 (1)°
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
5033 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS (Bruker)
3781 reflections with I > 2σ(I)
Tmin = 0.645, Tmax = 0.941Rint = 0.016
10578 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.49 e Å3
5033 reflectionsΔρmin = 0.31 e Å3
208 parameters
Special details top

Experimental. none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.22177 (4)0.61122 (2)0.798820 (11)0.03757 (9)
Cl10.06612 (9)0.63934 (6)0.88209 (3)0.05440 (16)
Cl20.29307 (11)0.42863 (5)0.80839 (3)0.06331 (18)
C30.1279 (3)0.57142 (19)0.64365 (10)0.0403 (4)
C40.1072 (3)0.6472 (2)0.58965 (11)0.0495 (5)
H4A0.07220.62720.54510.059*
C50.1467 (3)0.75510 (19)0.61340 (10)0.0437 (5)
C60.2442 (3)0.82428 (16)0.73257 (9)0.0326 (4)
C70.2356 (3)0.94055 (18)0.72394 (10)0.0385 (4)
H7A0.18530.97330.68320.046*
C80.3059 (3)1.00788 (17)0.77918 (10)0.0372 (4)
C90.3798 (3)0.84661 (17)0.84216 (9)0.0338 (4)
C100.4668 (3)0.79601 (17)0.90664 (9)0.0365 (4)
C110.4598 (4)0.8576 (2)0.96475 (11)0.0475 (5)
H11A0.39970.92840.96250.057*
C120.5420 (4)0.8135 (2)1.02579 (11)0.0591 (6)
H12A0.53480.85431.06450.071*
C130.6345 (4)0.7098 (2)1.02971 (12)0.0612 (7)
H13A0.69150.68091.07070.073*
C140.6416 (4)0.6491 (2)0.97225 (13)0.0612 (7)
H14A0.70340.57880.97480.073*
C150.5587 (3)0.6909 (2)0.91101 (11)0.0484 (5)
H15A0.56430.64880.87270.058*
C310.1028 (4)0.4456 (2)0.64134 (12)0.0525 (5)
H31A0.20120.41110.62180.079*
H31B0.01700.42720.61510.079*
H31C0.10790.41670.68570.079*
C510.1549 (5)0.8643 (2)0.57589 (12)0.0645 (7)
H51A0.13700.84820.52910.097*
H51B0.27530.89990.58950.097*
H51C0.05760.91510.58490.097*
C810.3017 (4)1.13550 (19)0.77637 (12)0.0475 (5)
H81A0.22631.16420.80720.071*
H81B0.24861.15980.73220.071*
H81C0.42741.16480.78790.071*
N10.1767 (2)0.63092 (14)0.69990 (8)0.0359 (3)
N20.1861 (2)0.74406 (14)0.68144 (7)0.0343 (3)
N30.3823 (2)0.96011 (15)0.83758 (8)0.0382 (3)
N40.3073 (2)0.77576 (13)0.79207 (7)0.0316 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.05027 (16)0.02815 (15)0.03428 (13)0.00253 (10)0.00721 (10)0.00130 (8)
Cl10.0670 (4)0.0582 (4)0.0416 (3)0.0201 (3)0.0195 (2)0.0094 (2)
Cl20.0957 (5)0.0316 (3)0.0609 (4)0.0076 (3)0.0084 (3)0.0073 (2)
C30.0404 (10)0.0406 (11)0.0401 (10)0.0012 (8)0.0072 (8)0.0105 (8)
C40.0630 (13)0.0507 (13)0.0327 (10)0.0021 (11)0.0019 (9)0.0085 (9)
C50.0571 (12)0.0446 (12)0.0280 (8)0.0041 (10)0.0032 (8)0.0006 (8)
C60.0358 (8)0.0299 (9)0.0319 (8)0.0008 (7)0.0053 (7)0.0035 (7)
C70.0453 (10)0.0344 (11)0.0344 (9)0.0028 (8)0.0030 (8)0.0041 (7)
C80.0403 (9)0.0297 (10)0.0414 (10)0.0002 (8)0.0067 (8)0.0016 (7)
C90.0363 (9)0.0313 (10)0.0329 (8)0.0010 (7)0.0031 (7)0.0013 (7)
C100.0411 (9)0.0344 (10)0.0320 (8)0.0049 (8)0.0008 (7)0.0012 (7)
C110.0638 (13)0.0390 (11)0.0370 (10)0.0001 (10)0.0007 (9)0.0060 (8)
C120.0775 (16)0.0640 (16)0.0326 (10)0.0022 (13)0.0003 (10)0.0065 (10)
C130.0712 (16)0.0657 (17)0.0400 (11)0.0013 (13)0.0099 (11)0.0083 (11)
C140.0763 (17)0.0500 (14)0.0507 (13)0.0179 (13)0.0081 (12)0.0042 (11)
C150.0601 (13)0.0437 (12)0.0382 (10)0.0093 (10)0.0009 (9)0.0029 (9)
C310.0629 (14)0.0424 (13)0.0521 (13)0.0073 (11)0.0092 (11)0.0149 (10)
C510.109 (2)0.0490 (14)0.0337 (11)0.0058 (14)0.0083 (12)0.0074 (9)
C810.0573 (12)0.0302 (11)0.0530 (13)0.0036 (9)0.0040 (10)0.0004 (9)
N10.0444 (8)0.0289 (8)0.0344 (8)0.0004 (6)0.0061 (6)0.0021 (6)
N20.0439 (8)0.0283 (8)0.0296 (7)0.0008 (6)0.0031 (6)0.0008 (6)
N30.0439 (8)0.0330 (9)0.0366 (8)0.0027 (7)0.0035 (7)0.0007 (6)
N40.0367 (7)0.0280 (8)0.0291 (7)0.0016 (6)0.0034 (6)0.0005 (6)
Geometric parameters (Å, º) top
Cu1—N12.0011 (16)C10—C151.388 (3)
Cu1—N42.0259 (15)C10—C111.394 (3)
Cu1—Cl22.1898 (6)C11—C121.383 (3)
Cu1—Cl12.2147 (6)C11—H11A0.9300
C3—N11.335 (2)C12—C131.377 (4)
C3—C41.399 (3)C12—H12A0.9300
C3—C311.477 (3)C13—C141.377 (4)
C4—C51.360 (3)C13—H13A0.9300
C4—H4A0.9300C14—C151.378 (3)
C5—N21.374 (2)C14—H14A0.9300
C5—C511.491 (3)C15—H15A0.9300
C6—N41.346 (2)C31—H31A0.9600
C6—C71.366 (3)C31—H31B0.9600
C6—N21.410 (2)C31—H31C0.9600
C7—C81.395 (3)C51—H51A0.9600
C7—H7A0.9300C51—H51B0.9600
C8—N31.345 (3)C51—H51C0.9600
C8—C811.488 (3)C81—H81A0.9600
C9—N31.326 (3)C81—H81B0.9600
C9—N41.348 (2)C81—H81C0.9600
C9—C101.480 (3)N1—N21.376 (2)
N1—Cu1—N479.74 (6)C12—C13—H13A120.4
N1—Cu1—Cl2101.34 (5)C14—C13—H13A120.4
N4—Cu1—Cl2148.86 (5)C13—C14—C15121.1 (2)
N1—Cu1—Cl1137.72 (5)C13—C14—H14A119.4
N4—Cu1—Cl196.45 (5)C15—C14—H14A119.4
Cl2—Cu1—Cl1102.57 (3)C14—C15—C10119.9 (2)
N1—C3—C4109.01 (19)C14—C15—H15A120.1
N1—C3—C31123.8 (2)C10—C15—H15A120.1
C4—C3—C31127.23 (19)C3—C31—H31A109.5
C5—C4—C3108.37 (18)C3—C31—H31B109.5
C5—C4—H4A125.8H31A—C31—H31B109.5
C3—C4—H4A125.8C3—C31—H31C109.5
C4—C5—N2105.53 (18)H31A—C31—H31C109.5
C4—C5—C51129.09 (19)H31B—C31—H31C109.5
N2—C5—C51125.3 (2)C5—C51—H51A109.5
N4—C6—C7122.26 (17)C5—C51—H51B109.5
N4—C6—N2113.61 (16)H51A—C51—H51B109.5
C7—C6—N2124.12 (17)C5—C51—H51C109.5
C6—C7—C8116.83 (18)H51A—C51—H51C109.5
C6—C7—H7A121.6H51B—C51—H51C109.5
C8—C7—H7A121.6C8—C81—H81A109.5
N3—C8—C7121.33 (18)C8—C81—H81B109.5
N3—C8—C81116.76 (19)H81A—C81—H81B109.5
C7—C8—C81121.91 (19)C8—C81—H81C109.5
N3—C9—N4124.45 (17)H81A—C81—H81C109.5
N3—C9—C10116.82 (16)H81B—C81—H81C109.5
N4—C9—C10118.72 (17)C3—N1—N2106.29 (16)
C15—C10—C11119.08 (19)C3—N1—Cu1141.28 (15)
C15—C10—C9122.27 (18)N2—N1—Cu1112.25 (11)
C11—C10—C9118.63 (19)N1—N2—C5110.77 (16)
C12—C11—C10120.1 (2)N1—N2—C6117.08 (15)
C12—C11—H11A119.9C5—N2—C6131.99 (17)
C10—C11—H11A119.9C9—N3—C8117.82 (17)
C13—C12—C11120.5 (2)C6—N4—C9116.99 (16)
C13—C12—H12A119.8C6—N4—Cu1113.51 (12)
C11—C12—H12A119.8C9—N4—Cu1127.70 (13)
C12—C13—C14119.3 (2)
N1—N2—C6—N48.6 (2)N4—C9—C10—C1532.0 (3)
(2eg) (4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenyl-pyrimidyne)dichlorocopper(II) emerald green form top
Crystal data top
C16H16Cl2CuN4Dx = 1.574 Mg m3
Mr = 398.77Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 4601 reflections
a = 11.6899 (6) Åθ = 2.5–30.5°
b = 14.9843 (8) ŵ = 1.62 mm1
c = 19.2115 (9) ÅT = 293 K
V = 3365.2 (3) Å3Elongated prism, clear emerald green
Z = 80.33 × 0.10 × 0.09 mm
F(000) = 1624
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
5379 independent reflections
Radiation source: fine-focus sealed tube3611 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 25 pixels mm-1θmax = 32.4°, θmin = 2.1°
π–scansh = 1617
Absorption correction: empirical (using intensity measurements)
SADABS (Bruker)
k = 1722
Tmin = 0.657, Tmax = 0.86l = 2615
17334 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) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 0.86 w = 1/[σ2(Fo2) + (0.053P)2 + 2.2199P]
where P = (Fo2 + 2Fc2)/3
5379 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C16H16Cl2CuN4V = 3365.2 (3) Å3
Mr = 398.77Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.6899 (6) ŵ = 1.62 mm1
b = 14.9843 (8) ÅT = 293 K
c = 19.2115 (9) Å0.33 × 0.10 × 0.09 mm
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
5379 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS (Bruker)
3611 reflections with I > 2σ(I)
Tmin = 0.657, Tmax = 0.86Rint = 0.024
17334 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 0.86Δρmax = 0.49 e Å3
5379 reflectionsΔρmin = 0.44 e Å3
208 parameters
Special details top

Experimental. none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.751430 (18)0.839560 (17)0.548815 (12)0.03193 (8)
Cl10.71694 (4)0.74685 (4)0.63721 (3)0.04276 (13)
Cl20.93311 (4)0.86988 (5)0.56060 (3)0.05205 (15)
C30.79496 (17)0.81698 (14)0.38867 (10)0.0364 (4)
C40.72127 (18)0.80284 (16)0.33277 (11)0.0403 (5)
H4A0.74280.78690.28790.048*
C50.61204 (17)0.81652 (13)0.35544 (10)0.0337 (4)
C60.54197 (15)0.86338 (12)0.47575 (9)0.0281 (3)
C70.42510 (15)0.86907 (13)0.46564 (10)0.0323 (4)
H7A0.39150.85400.42330.039*
C80.36002 (16)0.89850 (13)0.52199 (10)0.0330 (4)
C90.52140 (15)0.91422 (12)0.58829 (9)0.0297 (4)
C100.57579 (16)0.94086 (13)0.65468 (9)0.0321 (4)
C110.5195 (2)0.92555 (15)0.71717 (11)0.0450 (5)
H11A0.44600.90190.71720.054*
C120.5732 (3)0.94568 (18)0.77950 (12)0.0581 (6)
H12A0.53620.93420.82140.070*
C130.6811 (2)0.98264 (18)0.77971 (12)0.0563 (6)
H13A0.71690.99520.82180.068*
C140.7361 (2)1.00108 (16)0.71794 (13)0.0478 (5)
H14A0.80781.02800.71820.057*
C150.68394 (17)0.97928 (14)0.65567 (10)0.0368 (4)
H15A0.72170.99050.61390.044*
C310.92214 (18)0.81407 (19)0.38827 (12)0.0521 (6)
H31A0.95160.87240.37790.078*
H31B0.94770.77260.35350.078*
H31C0.94920.79540.43310.078*
C510.50499 (19)0.81183 (17)0.31405 (10)0.0452 (5)
H51A0.52290.79550.26700.068*
H51B0.46800.86900.31450.068*
H51C0.45490.76790.33390.068*
C810.23295 (17)0.90503 (17)0.51881 (13)0.0442 (5)
H81A0.20010.87210.55670.066*
H81B0.20640.88070.47550.066*
H81C0.21050.96650.52220.066*
N10.73495 (12)0.83749 (11)0.44553 (8)0.0316 (3)
N20.62136 (13)0.83753 (10)0.42500 (8)0.0295 (3)
N30.40850 (13)0.92337 (11)0.58266 (9)0.0348 (4)
N40.58950 (12)0.88237 (11)0.53781 (8)0.0282 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02606 (11)0.04428 (15)0.02545 (13)0.00235 (9)0.00037 (8)0.00186 (9)
Cl10.0403 (2)0.0539 (3)0.0341 (3)0.0093 (2)0.00545 (19)0.0107 (2)
Cl20.0298 (2)0.0792 (4)0.0471 (3)0.0078 (3)0.0035 (2)0.0021 (3)
C30.0355 (9)0.0458 (11)0.0278 (9)0.0054 (8)0.0088 (8)0.0050 (8)
C40.0449 (11)0.0511 (12)0.0248 (9)0.0053 (9)0.0065 (8)0.0002 (9)
C50.0386 (10)0.0389 (10)0.0236 (9)0.0004 (8)0.0004 (7)0.0000 (7)
C60.0290 (8)0.0304 (8)0.0247 (8)0.0004 (7)0.0013 (7)0.0022 (7)
C70.0286 (8)0.0389 (10)0.0294 (9)0.0002 (7)0.0020 (7)0.0002 (8)
C80.0284 (8)0.0382 (10)0.0323 (10)0.0006 (7)0.0004 (7)0.0015 (8)
C90.0305 (8)0.0324 (9)0.0260 (8)0.0020 (7)0.0029 (7)0.0017 (7)
C100.0358 (9)0.0360 (9)0.0244 (9)0.0053 (7)0.0011 (7)0.0023 (7)
C110.0493 (12)0.0528 (13)0.0330 (11)0.0025 (10)0.0087 (9)0.0046 (9)
C120.0818 (18)0.0668 (16)0.0257 (10)0.0018 (14)0.0073 (11)0.0009 (11)
C130.0766 (17)0.0598 (15)0.0325 (11)0.0008 (13)0.0136 (11)0.0066 (10)
C140.0492 (13)0.0523 (13)0.0419 (12)0.0002 (10)0.0119 (10)0.0059 (10)
C150.0368 (9)0.0426 (10)0.0311 (10)0.0035 (8)0.0003 (8)0.0032 (8)
C310.0365 (11)0.0822 (17)0.0378 (12)0.0125 (11)0.0109 (9)0.0074 (12)
C510.0436 (11)0.0653 (14)0.0269 (10)0.0024 (10)0.0045 (8)0.0068 (10)
C810.0298 (10)0.0566 (14)0.0461 (13)0.0012 (9)0.0020 (8)0.0020 (10)
N10.0261 (7)0.0437 (9)0.0250 (8)0.0029 (6)0.0019 (5)0.0011 (6)
N20.0257 (7)0.0402 (8)0.0225 (7)0.0021 (6)0.0012 (6)0.0015 (6)
N30.0302 (8)0.0418 (9)0.0325 (8)0.0028 (6)0.0025 (6)0.0025 (7)
N40.0268 (7)0.0344 (8)0.0233 (7)0.0016 (6)0.0003 (5)0.0011 (6)
Geometric parameters (Å, º) top
Cu1—N11.9938 (16)C10—C151.389 (3)
Cu1—N42.0098 (15)C10—C111.388 (3)
Cu1—Cl22.1836 (6)C11—C121.385 (3)
Cu1—Cl12.2307 (6)C11—H11A0.9300
C3—N11.334 (2)C12—C131.377 (4)
C3—C41.393 (3)C12—H12A0.9300
C3—C311.487 (3)C13—C141.378 (3)
C4—C51.365 (3)C13—H13A0.9300
C4—H4A0.9300C14—C151.382 (3)
C5—N21.377 (2)C14—H14A0.9300
C5—C511.484 (3)C15—H15A0.9300
C6—N41.346 (2)C31—H31A0.9600
C6—C71.383 (2)C31—H31B0.9600
C6—N21.401 (2)C31—H31C0.9600
C7—C81.395 (3)C51—H51A0.9600
C7—H7A0.9300C51—H51B0.9600
C8—N31.349 (3)C51—H51C0.9600
C8—C811.490 (3)C81—H81A0.9600
C9—N31.331 (2)C81—H81B0.9600
C9—N41.342 (2)C81—H81C0.9600
C9—C101.480 (3)N1—N21.385 (2)
N1—Cu1—N479.01 (6)C12—C13—H13A119.8
N1—Cu1—Cl2101.56 (5)C14—C13—H13A119.8
N4—Cu1—Cl2149.38 (5)C13—C14—C15119.4 (2)
N1—Cu1—Cl1136.93 (5)C13—C14—H14A120.3
N4—Cu1—Cl196.23 (5)C15—C14—H14A120.3
Cl2—Cu1—Cl1103.09 (2)C14—C15—C10120.8 (2)
N1—C3—C4109.95 (17)C14—C15—H15A119.6
N1—C3—C31122.45 (19)C10—C15—H15A119.6
C4—C3—C31127.57 (18)C3—C31—H31A109.5
C5—C4—C3108.05 (18)C3—C31—H31B109.5
C5—C4—H4A126.0H31A—C31—H31B109.5
C3—C4—H4A126.0C3—C31—H31C109.5
C4—C5—N2105.66 (17)H31A—C31—H31C109.5
C4—C5—C51127.65 (18)H31B—C31—H31C109.5
N2—C5—C51126.68 (18)C5—C51—H51A109.5
N4—C6—C7121.29 (16)C5—C51—H51B109.5
N4—C6—N2113.68 (15)H51A—C51—H51B109.5
C7—C6—N2125.02 (17)C5—C51—H51C109.5
C6—C7—C8116.71 (17)H51A—C51—H51C109.5
C6—C7—H7A121.6H51B—C51—H51C109.5
C8—C7—H7A121.6C8—C81—H81A109.5
N3—C8—C7121.94 (17)C8—C81—H81B109.5
N3—C8—C81115.87 (18)H81A—C81—H81B109.5
C7—C8—C81122.19 (19)C8—C81—H81C109.5
N3—C9—N4124.47 (17)H81A—C81—H81C109.5
N3—C9—C10117.91 (16)H81B—C81—H81C109.5
N4—C9—C10117.62 (16)C3—N1—N2105.72 (16)
C15—C10—C11119.20 (19)C3—N1—Cu1140.14 (14)
C15—C10—C9120.97 (17)N2—N1—Cu1112.09 (11)
C11—C10—C9119.82 (18)C5—N2—N1110.61 (14)
C12—C11—C10119.8 (2)C5—N2—C6133.33 (16)
C12—C11—H11A120.1N1—N2—C6115.91 (14)
C10—C11—H11A120.1C9—N3—C8117.28 (16)
C13—C12—C11120.3 (2)C9—N4—C6118.05 (15)
C13—C12—H12A119.8C9—N4—Cu1126.59 (12)
C11—C12—H12A119.8C6—N4—Cu1114.49 (12)
C12—C13—C14120.4 (2)
N1—N2—C6—N41.5 (2)N4—C9—C10—C1535.2 (3)
(2o) (4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenyl-pyrimidyne)dichlorocopper(II) orange form top
Crystal data top
C16H16Cl2CuN4Z = 4
Mr = 398.77F(000) = 812
Monoclinic, P21/nDx = 1.554 Mg m3
a = 9.7652 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 18.7631 (10) ŵ = 1.60 mm1
c = 9.8115 (4) ÅT = 293 K
β = 108.544 (1)°Prism, clear orange
V = 1704.38 (16) Å30.31 × 0.17 × 0.12 mm
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
3915 independent reflections
Radiation source: fine-focus sealed tube3240 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 25 pixels mm-1θmax = 27.6°, θmin = 2.2°
π–scansh = 1212
Absorption correction: empirical (using intensity measurements)
SADABS (Bruker)
k = 2424
Tmin = 0.721, Tmax = 0.820l = 128
12988 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.2601P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
3915 reflectionsΔρmax = 0.38 e Å3
209 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (6)
Crystal data top
C16H16Cl2CuN4V = 1704.38 (16) Å3
Mr = 398.77Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.7652 (6) ŵ = 1.60 mm1
b = 18.7631 (10) ÅT = 293 K
c = 9.8115 (4) Å0.31 × 0.17 × 0.12 mm
β = 108.544 (1)°
Data collection top
Bruker-Nonius X8Apex CCD area-detector
diffractometer
3915 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS (Bruker)
3240 reflections with I > 2σ(I)
Tmin = 0.721, Tmax = 0.820Rint = 0.019
12988 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.38 e Å3
3915 reflectionsΔρmin = 0.28 e Å3
209 parameters
Special details top

Experimental. none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.35577 (2)0.953703 (11)0.63529 (2)0.03640 (10)
Cl10.26509 (5)0.85393 (2)0.69352 (5)0.04572 (14)
Cl20.26863 (6)0.95797 (3)0.39918 (5)0.04932 (14)
C30.2445 (2)1.10742 (10)0.6439 (2)0.0429 (4)
C40.2987 (2)1.16774 (11)0.7277 (2)0.0471 (5)
H4A0.25281.21170.72070.056*
C50.4302 (2)1.15061 (9)0.8209 (2)0.0406 (4)
C60.56506 (19)1.03183 (9)0.85684 (19)0.0342 (4)
C70.68466 (19)1.04774 (11)0.9723 (2)0.0423 (5)
H7A0.69631.09241.01570.051*
C80.7868 (2)0.99460 (12)1.0210 (2)0.0443 (5)
C90.65500 (18)0.91947 (10)0.84397 (19)0.0375 (4)
C100.6418 (2)0.84987 (10)0.7705 (2)0.0410 (4)
C110.6852 (3)0.78836 (12)0.8515 (3)0.0578 (6)
H11A0.73060.79170.95020.069*
C120.6613 (3)0.72257 (13)0.7865 (4)0.0756 (8)
H12A0.68790.68140.84140.091*
C130.5983 (3)0.71794 (13)0.6405 (4)0.0763 (8)
H13A0.58080.67330.59700.092*
C140.5605 (3)0.77812 (13)0.5572 (3)0.0624 (6)
H14A0.52040.77430.45790.075*
C150.5823 (2)0.84446 (11)0.6220 (2)0.0477 (5)
H15A0.55730.88540.56620.057*
C310.1050 (2)1.09956 (12)0.5253 (3)0.0616 (6)
H31A0.11361.12040.43910.092*
H31B0.02981.12330.55130.092*
H31C0.08181.04990.50930.092*
C510.5336 (2)1.19784 (11)0.9267 (2)0.0569 (6)
H51A0.49121.24410.92490.085*
H51B0.62091.20200.90210.085*
H51C0.55541.17781.02120.085*
C810.9208 (2)1.00655 (15)1.1464 (2)0.0600 (6)
H81A0.96610.96161.17930.090*
H81B0.89561.02931.22270.090*
H81C0.98631.03641.11720.090*
N10.33813 (17)1.05425 (8)0.68426 (18)0.0390 (4)
N20.45345 (15)1.07999 (8)0.79458 (15)0.0347 (3)
N30.77311 (17)0.93061 (10)0.95595 (18)0.0444 (4)
N40.54687 (15)0.96688 (8)0.79507 (16)0.0335 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03786 (15)0.02895 (14)0.03432 (15)0.00187 (8)0.00005 (10)0.00082 (8)
Cl10.0478 (3)0.0376 (2)0.0470 (3)0.00841 (19)0.0084 (2)0.00478 (19)
Cl20.0595 (3)0.0456 (3)0.0339 (3)0.0068 (2)0.0021 (2)0.00339 (19)
C30.0396 (10)0.0349 (9)0.0474 (11)0.0041 (8)0.0040 (8)0.0022 (8)
C40.0518 (11)0.0323 (9)0.0528 (12)0.0057 (8)0.0105 (9)0.0013 (8)
C50.0471 (10)0.0319 (9)0.0418 (10)0.0038 (8)0.0129 (8)0.0032 (7)
C60.0314 (8)0.0376 (9)0.0326 (9)0.0026 (7)0.0088 (7)0.0018 (7)
C70.0336 (9)0.0495 (12)0.0394 (10)0.0036 (8)0.0054 (8)0.0087 (8)
C80.0307 (9)0.0649 (13)0.0346 (10)0.0019 (8)0.0068 (7)0.0007 (9)
C90.0318 (9)0.0424 (10)0.0366 (9)0.0008 (7)0.0088 (7)0.0076 (8)
C100.0327 (9)0.0387 (10)0.0514 (11)0.0053 (7)0.0132 (8)0.0055 (8)
C110.0554 (12)0.0485 (12)0.0692 (15)0.0161 (10)0.0196 (11)0.0142 (11)
C120.0837 (19)0.0426 (13)0.107 (2)0.0169 (12)0.0389 (17)0.0165 (14)
C130.0863 (19)0.0384 (13)0.119 (3)0.0027 (12)0.0530 (19)0.0159 (14)
C140.0599 (14)0.0604 (15)0.0714 (16)0.0038 (11)0.0275 (12)0.0180 (12)
C150.0475 (11)0.0422 (11)0.0539 (12)0.0044 (9)0.0170 (9)0.0004 (9)
C310.0465 (12)0.0489 (12)0.0682 (15)0.0092 (10)0.0116 (11)0.0003 (11)
C510.0603 (14)0.0404 (11)0.0605 (14)0.0071 (10)0.0058 (11)0.0121 (10)
C810.0346 (11)0.0918 (18)0.0442 (12)0.0022 (11)0.0010 (9)0.0068 (12)
N10.0359 (8)0.0322 (8)0.0392 (8)0.0001 (6)0.0017 (6)0.0030 (6)
N20.0315 (7)0.0316 (7)0.0346 (8)0.0024 (6)0.0015 (6)0.0036 (6)
N30.0322 (8)0.0555 (10)0.0412 (9)0.0061 (7)0.0058 (7)0.0051 (8)
N40.0297 (7)0.0343 (7)0.0332 (8)0.0005 (6)0.0055 (6)0.0024 (6)
Geometric parameters (Å, º) top
Cu1—N11.9679 (15)C10—C111.389 (3)
Cu1—N42.0348 (14)C10—C151.391 (3)
Cu1—Cl22.2008 (5)C11—C121.375 (4)
Cu1—Cl12.2219 (5)C11—H11A0.9300
C3—N11.326 (2)C12—C131.371 (4)
C3—C41.400 (3)C12—H12A0.9300
C3—C311.491 (3)C13—C141.374 (4)
C4—C51.357 (3)C13—H13A0.9300
C4—H4A0.9300C14—C151.383 (3)
C5—N21.383 (2)C14—H14A0.9300
C5—C511.488 (3)C15—H15A0.9300
C6—N41.347 (2)C31—H31A0.9600
C6—C71.376 (2)C31—H31B0.9600
C6—N21.398 (2)C31—H31C0.9600
C7—C81.384 (3)C51—H51A0.9600
C7—H7A0.9300C51—H51B0.9600
C8—N31.346 (3)C51—H51C0.9600
C8—C811.500 (3)C81—H81A0.9600
C9—N31.332 (2)C81—H81B0.9600
C9—N41.347 (2)C81—H81C0.9600
C9—C101.477 (3)N1—N21.378 (2)
N1—Cu1—N479.95 (6)C12—C13—H13A119.5
N1—Cu1—Cl2100.81 (5)C14—C13—H13A119.5
N4—Cu1—Cl2139.41 (5)C13—C14—C15119.6 (2)
N1—Cu1—Cl1132.22 (5)C13—C14—H14A120.2
N4—Cu1—Cl1104.31 (4)C15—C14—H14A120.2
Cl2—Cu1—Cl1104.42 (2)C14—C15—C10119.9 (2)
N1—C3—C4109.70 (17)C14—C15—H15A120.0
N1—C3—C31122.06 (18)C10—C15—H15A120.0
C4—C3—C31128.24 (18)C3—C31—H31A109.5
C5—C4—C3107.71 (17)C3—C31—H31B109.5
C5—C4—H4A126.1H31A—C31—H31B109.5
C3—C4—H4A126.1C3—C31—H31C109.5
C4—C5—N2106.10 (16)H31A—C31—H31C109.5
C4—C5—C51127.99 (18)H31B—C31—H31C109.5
N2—C5—C51125.85 (18)C5—C51—H51A109.5
N4—C6—C7121.49 (17)C5—C51—H51B109.5
N4—C6—N2114.53 (15)H51A—C51—H51B109.5
C7—C6—N2123.99 (17)C5—C51—H51C109.5
C6—C7—C8117.25 (18)H51A—C51—H51C109.5
C6—C7—H7A121.4H51B—C51—H51C109.5
C8—C7—H7A121.4C8—C81—H81A109.5
N3—C8—C7121.79 (17)C8—C81—H81B109.5
N3—C8—C81116.82 (19)H81A—C81—H81B109.5
C7—C8—C81121.4 (2)C8—C81—H81C109.5
N3—C9—N4124.41 (18)H81A—C81—H81C109.5
N3—C9—C10117.35 (17)H81B—C81—H81C109.5
N4—C9—C10118.24 (16)C3—N1—N2106.54 (14)
C11—C10—C15119.2 (2)C3—N1—Cu1138.95 (13)
C11—C10—C9119.50 (19)N2—N1—Cu1114.50 (11)
C15—C10—C9121.23 (17)N1—N2—C5109.94 (14)
C12—C11—C10120.4 (2)N1—N2—C6116.47 (14)
C12—C11—H11A119.8C5—N2—C6133.58 (15)
C10—C11—H11A119.8C9—N3—C8117.41 (17)
C13—C12—C11119.7 (2)C9—N4—C6117.44 (15)
C13—C12—H12A120.2C9—N4—Cu1128.11 (13)
C11—C12—H12A120.2C6—N4—Cu1114.45 (11)
C12—C13—C14121.0 (2)
N1—N2—C6—N42.8 (2)N4—C9—C10—C1538.6 (3)

Experimental details

(1)(2g)(2eg)(2o)
Crystal data
Chemical formulaC16H16N4C16H16Cl2CuN4C16H16Cl2CuN4C16H16Cl2CuN4
Mr264.33398.77398.77398.77
Crystal system, space groupOrthorhombic, Pna21Monoclinic, P21/cOrthorhombic, PbcaMonoclinic, P21/n
Temperature (K)293293293293
a, b, c (Å)19.499 (3), 4.7884 (6), 15.106 (2)7.2156 (3), 11.6522 (4), 20.3956 (8)11.6899 (6), 14.9843 (8), 19.2115 (9)9.7652 (6), 18.7631 (10), 9.8115 (4)
α, β, γ (°)90, 90, 9090, 99.841 (1), 9090, 90, 9090, 108.544 (1), 90
V3)1410.5 (4)1689.58 (11)3365.2 (3)1704.38 (16)
Z4484
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.081.611.621.60
Crystal size (mm)0.59 × 0.05 × 0.030.54 × 0.23 × 0.040.33 × 0.10 × 0.090.31 × 0.17 × 0.12
Data collection
DiffractometerBruker-Nonius X8Apex CCD area-detector
diffractometer
Bruker-Nonius X8Apex CCD area-detector
diffractometer
Bruker-Nonius X8Apex CCD area-detector
diffractometer
Bruker-Nonius X8Apex CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
SADABS (Bruker)
Empirical (using intensity measurements)
SADABS (Bruker)
Empirical (using intensity measurements)
SADABS (Bruker)
Tmin, Tmax0.645, 0.9410.657, 0.860.721, 0.820
No. of measured, independent and
observed [I > 2σ(I)] reflections
9460, 2221, 885 10578, 5033, 3781 17334, 5379, 3611 12988, 3915, 3240
Rint0.0830.0160.0240.019
(sin θ/λ)max1)0.7150.7570.7530.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.181, 0.91 0.033, 0.107, 0.94 0.032, 0.098, 0.86 0.029, 0.088, 1.10
No. of reflections2221503353793915
No. of parameters182208208209
No. of restraints1000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.150.49, 0.310.49, 0.440.38, 0.28
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881???
Absolute structure parameter0 (10)???

Computer programs: Bruker APEX2, Bruker SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Bruker SHELXTL, TOPOS 4.0 Standard, local programs.

 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds