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In the title compound, [CuCl2(C20H14N4)], the coordination around the Cu atom is approximately square-planar. The dihedral angle between the pyridine and triazine rings is 5.26 (5)°. The crystal structure is stabilized by C—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013050/ci2313sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013050/ci2313Isup2.hkl
Contains datablock I

CCDC reference: 642949

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.070
  • Data-to-parameter ratio = 45.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. CL1 .. 2.90 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 40.00 From the CIF: _reflns_number_total 11016 Count of symmetry unique reflns 5756 Completeness (_total/calc) 191.38% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 5260 Fraction of Friedel pairs measured 0.914 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Dichlorido[5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine]copper(II) top
Crystal data top
[CuCl2(C20H14N4)]F(000) = 3600
Mr = 444.79Dx = 1.657 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 9300 reflections
a = 12.8511 (1) Åθ = 2.6–40.0°
b = 55.1550 (6) ŵ = 1.54 mm1
c = 10.0623 (1) ÅT = 100 K
V = 7132.18 (12) Å3Block, green
Z = 160.41 × 0.30 × 0.27 mm
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer
11016 independent reflections
Radiation source: fine-focus sealed tube9834 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 8.33 pixels mm-1θmax = 40.0°, θmin = 1.5°
ω scansh = 2323
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 9998
Tmin = 0.550, Tmax = 0.681l = 1818
90380 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)] = 0.025H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0343P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
11016 reflectionsΔρmax = 0.47 e Å3
244 parametersΔρmin = 0.45 e Å3
1 restraintAbsolute structure: Flack (1983), 5261 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.010 (4)
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cu10.125094 (10)0.102606 (3)0.447935 (10)0.01128 (3)
Cl10.13026 (2)0.098031 (6)0.23021 (2)0.01688 (5)
Cl20.11409 (2)0.063019 (5)0.48422 (3)0.01988 (5)
N10.12410 (6)0.110297 (18)0.64544 (9)0.01213 (14)
N20.12568 (6)0.139482 (17)0.44028 (9)0.01228 (13)
N30.13883 (7)0.152914 (18)0.33090 (9)0.01369 (14)
N40.11607 (7)0.174279 (18)0.57761 (9)0.01335 (14)
C10.12144 (8)0.09438 (2)0.74582 (11)0.01465 (17)
H1A0.12160.07790.72660.018*
C20.11849 (8)0.10175 (2)0.87811 (11)0.01527 (17)
H2A0.11740.09030.94590.018*
C30.11717 (8)0.12627 (2)0.90821 (11)0.01590 (17)
H3A0.11470.13150.99600.019*
C40.11958 (8)0.14292 (2)0.80390 (11)0.01503 (17)
H4A0.11900.15950.82060.018*
C50.12292 (7)0.13418 (2)0.67482 (10)0.01228 (15)
C60.12332 (7)0.150374 (19)0.55855 (10)0.01197 (15)
C70.12270 (7)0.18815 (2)0.46968 (10)0.01264 (15)
C80.14489 (8)0.176944 (19)0.34463 (10)0.01321 (15)
C90.10442 (8)0.214239 (19)0.48741 (10)0.01382 (15)
C100.13670 (8)0.22531 (2)0.60596 (10)0.01611 (18)
H10A0.16970.21620.67130.019*
C110.11948 (8)0.24990 (2)0.62590 (12)0.01753 (18)
H11A0.14190.25720.70410.021*
C120.06878 (9)0.26365 (2)0.52945 (11)0.01857 (18)
H12A0.05740.28010.54290.022*
C130.03541 (9)0.25255 (2)0.41298 (12)0.01983 (19)
H13A0.00060.26160.34910.024*
C140.05330 (9)0.22815 (2)0.39077 (11)0.01700 (17)
H14A0.03150.22100.31190.020*
C150.17930 (8)0.190755 (18)0.22668 (10)0.01441 (15)
C160.26263 (9)0.20692 (2)0.24142 (12)0.01934 (18)
H16A0.29350.20900.32420.023*
C170.29907 (11)0.21979 (2)0.13196 (13)0.0239 (2)
H17A0.35510.23030.14120.029*
C180.25178 (11)0.21686 (2)0.00922 (12)0.0241 (2)
H18A0.27570.22560.06370.029*
C190.16898 (11)0.20097 (2)0.00543 (11)0.0209 (2)
H19A0.13740.19920.08800.025*
C200.13264 (8)0.18763 (2)0.10273 (11)0.01634 (18)
H20A0.07790.17680.09230.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01368 (5)0.00944 (5)0.01072 (4)0.00019 (4)0.00024 (3)0.00018 (3)
Cl10.02276 (12)0.01660 (11)0.01128 (9)0.00195 (8)0.00030 (8)0.00133 (7)
Cl20.03364 (14)0.00994 (11)0.01607 (9)0.00028 (9)0.00393 (10)0.00065 (8)
N10.0130 (3)0.0109 (4)0.0125 (3)0.0008 (2)0.0000 (2)0.0003 (2)
N20.0151 (3)0.0105 (3)0.0113 (3)0.0002 (3)0.0007 (2)0.0001 (2)
N30.0180 (4)0.0111 (4)0.0120 (3)0.0002 (3)0.0003 (3)0.0006 (3)
N40.0165 (4)0.0102 (4)0.0133 (3)0.0002 (3)0.0000 (3)0.0004 (2)
C10.0166 (4)0.0142 (5)0.0131 (4)0.0021 (3)0.0005 (3)0.0016 (3)
C20.0167 (4)0.0169 (5)0.0122 (3)0.0028 (3)0.0004 (3)0.0026 (3)
C30.0175 (4)0.0183 (5)0.0119 (3)0.0001 (3)0.0010 (3)0.0002 (3)
C40.0193 (5)0.0132 (4)0.0126 (3)0.0004 (3)0.0002 (3)0.0011 (3)
C50.0125 (3)0.0123 (4)0.0120 (3)0.0006 (3)0.0008 (3)0.0003 (3)
C60.0129 (4)0.0110 (4)0.0120 (3)0.0001 (3)0.0003 (3)0.0003 (3)
C70.0131 (4)0.0114 (4)0.0134 (4)0.0003 (3)0.0001 (3)0.0010 (3)
C80.0162 (4)0.0106 (4)0.0128 (3)0.0002 (3)0.0001 (3)0.0000 (3)
C90.0161 (4)0.0107 (4)0.0147 (3)0.0003 (3)0.0005 (3)0.0017 (3)
C100.0210 (5)0.0131 (5)0.0142 (4)0.0014 (3)0.0004 (3)0.0014 (3)
C110.0219 (5)0.0138 (5)0.0169 (4)0.0006 (3)0.0005 (3)0.0035 (3)
C120.0218 (5)0.0125 (4)0.0214 (4)0.0016 (4)0.0006 (4)0.0038 (3)
C130.0257 (5)0.0126 (5)0.0212 (4)0.0038 (4)0.0040 (4)0.0013 (3)
C140.0208 (4)0.0132 (4)0.0169 (4)0.0023 (3)0.0034 (3)0.0027 (3)
C150.0190 (4)0.0108 (4)0.0135 (3)0.0017 (3)0.0032 (3)0.0007 (3)
C160.0237 (5)0.0142 (5)0.0202 (4)0.0027 (4)0.0026 (4)0.0000 (3)
C170.0297 (6)0.0154 (5)0.0265 (5)0.0048 (4)0.0087 (4)0.0006 (4)
C180.0378 (7)0.0136 (5)0.0208 (4)0.0005 (4)0.0120 (4)0.0025 (3)
C190.0333 (6)0.0153 (5)0.0142 (4)0.0053 (4)0.0038 (4)0.0010 (3)
C200.0223 (5)0.0124 (4)0.0143 (4)0.0018 (3)0.0022 (3)0.0003 (3)
Geometric parameters (Å, º) top
Cu1—N12.0321 (9)C9—C141.4021 (15)
Cu1—N22.0354 (9)C9—C101.4029 (15)
Cu1—Cl12.2063 (3)C10—C111.3888 (17)
Cu1—Cl22.2183 (3)C10—H10A0.9300
N1—C11.3388 (16)C11—C121.3933 (17)
N1—C51.3502 (15)C11—H11A0.9300
N2—C61.3335 (13)C12—C131.3901 (16)
N2—N31.3374 (13)C12—H12A0.9300
N3—C81.3348 (15)C13—C141.3836 (16)
N4—C71.3313 (14)C13—H13A0.9300
N4—C61.3356 (14)C14—H14A0.9300
C1—C21.3924 (17)C15—C201.3945 (15)
C1—H1A0.9300C15—C161.4014 (15)
C2—C31.3860 (17)C16—C171.3914 (16)
C2—H2A0.9300C16—H16A0.9300
C3—C41.3952 (16)C17—C181.3859 (19)
C3—H3A0.9300C17—H17A0.9300
C4—C51.3861 (15)C18—C191.3862 (19)
C4—H4A0.9300C18—H18A0.9300
C5—C61.4719 (14)C19—C201.3943 (16)
C7—C81.4306 (14)C19—H19A0.9300
C7—C91.4687 (15)C20—H20A0.9300
C8—C151.4780 (14)
N1—Cu1—N280.12 (4)C7—C8—C15122.90 (9)
N1—Cu1—Cl1174.36 (3)C14—C9—C10119.35 (10)
N2—Cu1—Cl194.39 (3)C14—C9—C7121.78 (9)
N1—Cu1—Cl292.53 (3)C10—C9—C7118.85 (10)
N2—Cu1—Cl2171.91 (3)C11—C10—C9120.06 (10)
Cl1—Cu1—Cl293.024 (11)C11—C10—H10A120.0
C1—N1—C5118.32 (10)C9—C10—H10A120.0
C1—N1—Cu1126.95 (9)C10—C11—C12120.36 (10)
C5—N1—Cu1114.70 (7)C10—C11—H11A119.8
C6—N2—N3119.19 (9)C12—C11—H11A119.8
C6—N2—Cu1114.60 (7)C13—C12—C11119.46 (10)
N3—N2—Cu1125.81 (7)C13—C12—H12A120.3
C8—N3—N2118.18 (9)C11—C12—H12A120.3
C7—N4—C6116.47 (9)C14—C13—C12120.89 (10)
N1—C1—C2122.04 (11)C14—C13—H13A119.6
N1—C1—H1A119.0C12—C13—H13A119.6
C2—C1—H1A119.0C13—C14—C9119.87 (10)
C3—C2—C1119.61 (10)C13—C14—H14A120.1
C3—C2—H2A120.2C9—C14—H14A120.1
C1—C2—H2A120.2C20—C15—C16120.12 (10)
C2—C3—C4118.55 (10)C20—C15—C8121.73 (9)
C2—C3—H3A120.7C16—C15—C8118.13 (9)
C4—C3—H3A120.7C17—C16—C15119.86 (11)
C5—C4—C3118.46 (11)C17—C16—H16A120.1
C5—C4—H4A120.8C15—C16—H16A120.1
C3—C4—H4A120.8C18—C17—C16119.89 (11)
N1—C5—C4123.02 (10)C18—C17—H17A120.1
N1—C5—C6114.70 (9)C16—C17—H17A120.1
C4—C5—C6122.27 (10)C17—C18—C19120.34 (10)
N2—C6—N4125.06 (10)C17—C18—H18A119.8
N2—C6—C5115.86 (9)C19—C18—H18A119.8
N4—C6—C5118.99 (9)C18—C19—C20120.51 (11)
N4—C7—C8118.81 (10)C18—C19—H19A119.7
N4—C7—C9116.98 (9)C20—C19—H19A119.7
C8—C7—C9124.20 (9)C19—C20—C15119.27 (11)
N3—C8—C7120.57 (9)C19—C20—H20A120.4
N3—C8—C15116.49 (9)C15—C20—H20A120.4
N2—Cu1—N1—C1178.72 (9)C6—N4—C7—C9174.04 (9)
Cl2—Cu1—N1—C12.12 (8)N2—N3—C8—C79.00 (15)
N2—Cu1—N1—C50.82 (7)N2—N3—C8—C15168.65 (9)
Cl2—Cu1—N1—C5175.79 (6)N4—C7—C8—N313.04 (15)
N1—Cu1—N2—C61.13 (7)C9—C7—C8—N3165.70 (10)
Cl1—Cu1—N2—C6179.79 (7)N4—C7—C8—C15164.45 (9)
N1—Cu1—N2—N3171.59 (8)C9—C7—C8—C1516.81 (15)
Cl1—Cu1—N2—N37.06 (8)N4—C7—C9—C14143.81 (10)
C6—N2—N3—C82.66 (14)C8—C7—C9—C1434.96 (15)
Cu1—N2—N3—C8175.08 (7)N4—C7—C9—C1034.48 (14)
C5—N1—C1—C20.59 (14)C8—C7—C9—C10146.76 (10)
Cu1—N1—C1—C2178.43 (7)C14—C9—C10—C111.04 (16)
N1—C1—C2—C30.67 (15)C7—C9—C10—C11179.37 (9)
C1—C2—C3—C40.44 (15)C9—C10—C11—C120.96 (16)
C2—C3—C4—C50.17 (16)C10—C11—C12—C130.06 (17)
C1—N1—C5—C40.30 (15)C11—C12—C13—C141.01 (18)
Cu1—N1—C5—C4178.40 (8)C12—C13—C14—C90.91 (18)
C1—N1—C5—C6178.51 (9)C10—C9—C14—C130.12 (17)
Cu1—N1—C5—C60.41 (10)C7—C9—C14—C13178.39 (10)
C3—C4—C5—N10.10 (16)N3—C8—C15—C2051.40 (14)
C3—C4—C5—C6178.62 (9)C7—C8—C15—C20131.01 (11)
N3—N2—C6—N411.56 (15)N3—C8—C15—C16127.17 (11)
Cu1—N2—C6—N4175.20 (8)C7—C8—C15—C1650.41 (14)
N3—N2—C6—C5172.00 (8)C20—C15—C16—C170.26 (17)
Cu1—N2—C6—C51.25 (11)C8—C15—C16—C17178.34 (10)
C7—N4—C6—N27.33 (15)C15—C16—C17—C181.01 (18)
C7—N4—C6—C5176.33 (8)C16—C17—C18—C190.67 (19)
N1—C5—C6—N20.56 (13)C17—C18—C19—C200.42 (18)
C4—C5—C6—N2179.38 (10)C18—C19—C20—C151.16 (17)
N1—C5—C6—N4176.11 (8)C16—C15—C20—C190.81 (16)
C4—C5—C6—N42.70 (15)C8—C15—C20—C19179.36 (10)
C6—N4—C7—C84.79 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···Cl20.932.583.151 (1)121
C2—H2A···Cl1i0.932.903.552 (1)129
C12—H12A···Cl2ii0.932.833.522 (1)132
Symmetry codes: (i) x, y, z+1; (ii) x+1/4, y+1/4, z+1/4.
 

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