Dichlorido[5,6-diphenyl-3-(2-pyrid­yl)-1,2,4-triazine]copper(II)

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.

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

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Computing details

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)

Crystal data

[CuCl2(C20H14N4)]	F(000) = 3600
Mr = 444.79	Dx = 1.657 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 9300 reflections
a = 12.8511 (1) Å	θ = 2.6–40.0°
b = 55.1550 (6) Å	µ = 1.54 mm^−1
c = 10.0623 (1) Å	T = 100 K
V = 7132.18 (12) Å^3	Block, green
Z = 16	0.41 × 0.30 × 0.27 mm

Data collection

Bruker SMART APEX II CCD area-detector diffractometer	11016 independent reflections
Radiation source: fine-focus sealed tube	9834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 8.33 pixels mm^-1	θmax = 40.0°, θmin = 1.5°
ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −99→98
Tmin = 0.550, Tmax = 0.681	l = −18→18
90380 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0343P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
11016 reflections	Δρmax = 0.47 e Å^−3
244 parameters	Δρmin = −0.45 e Å^−3
1 restraint	Absolute structure: Flack (1983), 5261 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.125094 (10)	0.102606 (3)	0.447935 (10)	0.01128 (3)
Cl1	0.13026 (2)	0.098031 (6)	0.23021 (2)	0.01688 (5)
Cl2	0.11409 (2)	0.063019 (5)	0.48422 (3)	0.01988 (5)
N1	0.12410 (6)	0.110297 (18)	0.64544 (9)	0.01213 (14)
N2	0.12568 (6)	0.139482 (17)	0.44028 (9)	0.01228 (13)
N3	0.13883 (7)	0.152914 (18)	0.33090 (9)	0.01369 (14)
N4	0.11607 (7)	0.174279 (18)	0.57761 (9)	0.01335 (14)
C1	0.12144 (8)	0.09438 (2)	0.74582 (11)	0.01465 (17)
H1A	0.1216	0.0779	0.7266	0.018*
C2	0.11849 (8)	0.10175 (2)	0.87811 (11)	0.01527 (17)
H2A	0.1174	0.0903	0.9459	0.018*
C3	0.11717 (8)	0.12627 (2)	0.90821 (11)	0.01590 (17)
H3A	0.1147	0.1315	0.9960	0.019*
C4	0.11958 (8)	0.14292 (2)	0.80390 (11)	0.01503 (17)
H4A	0.1190	0.1595	0.8206	0.018*
C5	0.12292 (7)	0.13418 (2)	0.67482 (10)	0.01228 (15)
C6	0.12332 (7)	0.150374 (19)	0.55855 (10)	0.01197 (15)
C7	0.12270 (7)	0.18815 (2)	0.46968 (10)	0.01264 (15)
C8	0.14489 (8)	0.176944 (19)	0.34463 (10)	0.01321 (15)
C9	0.10442 (8)	0.214239 (19)	0.48741 (10)	0.01382 (15)
C10	0.13670 (8)	0.22531 (2)	0.60596 (10)	0.01611 (18)
H10A	0.1697	0.2162	0.6713	0.019*
C11	0.11948 (8)	0.24990 (2)	0.62590 (12)	0.01753 (18)
H11A	0.1419	0.2572	0.7041	0.021*
C12	0.06878 (9)	0.26365 (2)	0.52945 (11)	0.01857 (18)
H12A	0.0574	0.2801	0.5429	0.022*
C13	0.03541 (9)	0.25255 (2)	0.41298 (12)	0.01983 (19)
H13A	0.0006	0.2616	0.3491	0.024*
C14	0.05330 (9)	0.22815 (2)	0.39077 (11)	0.01700 (17)
H14A	0.0315	0.2210	0.3119	0.020*
C15	0.17930 (8)	0.190755 (18)	0.22668 (10)	0.01441 (15)
C16	0.26263 (9)	0.20692 (2)	0.24142 (12)	0.01934 (18)
H16A	0.2935	0.2090	0.3242	0.023*
C17	0.29907 (11)	0.21979 (2)	0.13196 (13)	0.0239 (2)
H17A	0.3551	0.2303	0.1412	0.029*
C18	0.25178 (11)	0.21686 (2)	0.00922 (12)	0.0241 (2)
H18A	0.2757	0.2256	−0.0637	0.029*
C19	0.16898 (11)	0.20097 (2)	−0.00543 (11)	0.0209 (2)
H19A	0.1374	0.1992	−0.0880	0.025*
C20	0.13264 (8)	0.18763 (2)	0.10273 (11)	0.01634 (18)
H20A	0.0779	0.1768	0.0923	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01368 (5)	0.00944 (5)	0.01072 (4)	−0.00019 (4)	0.00024 (3)	−0.00018 (3)
Cl1	0.02276 (12)	0.01660 (11)	0.01128 (9)	−0.00195 (8)	−0.00030 (8)	−0.00133 (7)
Cl2	0.03364 (14)	0.00994 (11)	0.01607 (9)	−0.00028 (9)	0.00393 (10)	−0.00065 (8)
N1	0.0130 (3)	0.0109 (4)	0.0125 (3)	−0.0008 (2)	0.0000 (2)	0.0003 (2)
N2	0.0151 (3)	0.0105 (3)	0.0113 (3)	0.0002 (3)	0.0007 (2)	0.0001 (2)
N3	0.0180 (4)	0.0111 (4)	0.0120 (3)	0.0002 (3)	0.0003 (3)	0.0006 (3)
N4	0.0165 (4)	0.0102 (4)	0.0133 (3)	−0.0002 (3)	0.0000 (3)	−0.0004 (2)
C1	0.0166 (4)	0.0142 (5)	0.0131 (4)	−0.0021 (3)	−0.0005 (3)	0.0016 (3)
C2	0.0167 (4)	0.0169 (5)	0.0122 (3)	−0.0028 (3)	−0.0004 (3)	0.0026 (3)
C3	0.0175 (4)	0.0183 (5)	0.0119 (3)	0.0001 (3)	0.0010 (3)	0.0002 (3)
C4	0.0193 (5)	0.0132 (4)	0.0126 (3)	0.0004 (3)	0.0002 (3)	−0.0011 (3)
C5	0.0125 (3)	0.0123 (4)	0.0120 (3)	−0.0006 (3)	−0.0008 (3)	−0.0003 (3)
C6	0.0129 (4)	0.0110 (4)	0.0120 (3)	−0.0001 (3)	0.0003 (3)	−0.0003 (3)
C7	0.0131 (4)	0.0114 (4)	0.0134 (4)	0.0003 (3)	0.0001 (3)	−0.0010 (3)
C8	0.0162 (4)	0.0106 (4)	0.0128 (3)	0.0002 (3)	0.0001 (3)	0.0000 (3)
C9	0.0161 (4)	0.0107 (4)	0.0147 (3)	−0.0003 (3)	0.0005 (3)	−0.0017 (3)
C10	0.0210 (5)	0.0131 (5)	0.0142 (4)	−0.0014 (3)	−0.0004 (3)	−0.0014 (3)
C11	0.0219 (5)	0.0138 (5)	0.0169 (4)	−0.0006 (3)	0.0005 (3)	−0.0035 (3)
C12	0.0218 (5)	0.0125 (4)	0.0214 (4)	0.0016 (4)	−0.0006 (4)	−0.0038 (3)
C13	0.0257 (5)	0.0126 (5)	0.0212 (4)	0.0038 (4)	−0.0040 (4)	−0.0013 (3)
C14	0.0208 (4)	0.0132 (4)	0.0169 (4)	0.0023 (3)	−0.0034 (3)	−0.0027 (3)
C15	0.0190 (4)	0.0108 (4)	0.0135 (3)	0.0017 (3)	0.0032 (3)	0.0007 (3)
C16	0.0237 (5)	0.0142 (5)	0.0202 (4)	−0.0027 (4)	0.0026 (4)	0.0000 (3)
C17	0.0297 (6)	0.0154 (5)	0.0265 (5)	−0.0048 (4)	0.0087 (4)	0.0006 (4)
C18	0.0378 (7)	0.0136 (5)	0.0208 (4)	0.0005 (4)	0.0120 (4)	0.0025 (3)
C19	0.0333 (6)	0.0153 (5)	0.0142 (4)	0.0053 (4)	0.0038 (4)	0.0010 (3)
C20	0.0223 (5)	0.0124 (4)	0.0143 (4)	0.0018 (3)	0.0022 (3)	0.0003 (3)

Geometric parameters (Å, º)

Cu1—N1	2.0321 (9)	C9—C14	1.4021 (15)
Cu1—N2	2.0354 (9)	C9—C10	1.4029 (15)
Cu1—Cl1	2.2063 (3)	C10—C11	1.3888 (17)
Cu1—Cl2	2.2183 (3)	C10—H10A	0.9300
N1—C1	1.3388 (16)	C11—C12	1.3933 (17)
N1—C5	1.3502 (15)	C11—H11A	0.9300
N2—C6	1.3335 (13)	C12—C13	1.3901 (16)
N2—N3	1.3374 (13)	C12—H12A	0.9300
N3—C8	1.3348 (15)	C13—C14	1.3836 (16)
N4—C7	1.3313 (14)	C13—H13A	0.9300
N4—C6	1.3356 (14)	C14—H14A	0.9300
C1—C2	1.3924 (17)	C15—C20	1.3945 (15)
C1—H1A	0.9300	C15—C16	1.4014 (15)
C2—C3	1.3860 (17)	C16—C17	1.3914 (16)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.3952 (16)	C17—C18	1.3859 (19)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.3861 (15)	C18—C19	1.3862 (19)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.4719 (14)	C19—C20	1.3943 (16)
C7—C8	1.4306 (14)	C19—H19A	0.9300
C7—C9	1.4687 (15)	C20—H20A	0.9300
C8—C15	1.4780 (14)
N1—Cu1—N2	80.12 (4)	C7—C8—C15	122.90 (9)
N1—Cu1—Cl1	174.36 (3)	C14—C9—C10	119.35 (10)
N2—Cu1—Cl1	94.39 (3)	C14—C9—C7	121.78 (9)
N1—Cu1—Cl2	92.53 (3)	C10—C9—C7	118.85 (10)
N2—Cu1—Cl2	171.91 (3)	C11—C10—C9	120.06 (10)
Cl1—Cu1—Cl2	93.024 (11)	C11—C10—H10A	120.0
C1—N1—C5	118.32 (10)	C9—C10—H10A	120.0
C1—N1—Cu1	126.95 (9)	C10—C11—C12	120.36 (10)
C5—N1—Cu1	114.70 (7)	C10—C11—H11A	119.8
C6—N2—N3	119.19 (9)	C12—C11—H11A	119.8
C6—N2—Cu1	114.60 (7)	C13—C12—C11	119.46 (10)
N3—N2—Cu1	125.81 (7)	C13—C12—H12A	120.3
C8—N3—N2	118.18 (9)	C11—C12—H12A	120.3
C7—N4—C6	116.47 (9)	C14—C13—C12	120.89 (10)
N1—C1—C2	122.04 (11)	C14—C13—H13A	119.6
N1—C1—H1A	119.0	C12—C13—H13A	119.6
C2—C1—H1A	119.0	C13—C14—C9	119.87 (10)
C3—C2—C1	119.61 (10)	C13—C14—H14A	120.1
C3—C2—H2A	120.2	C9—C14—H14A	120.1
C1—C2—H2A	120.2	C20—C15—C16	120.12 (10)
C2—C3—C4	118.55 (10)	C20—C15—C8	121.73 (9)
C2—C3—H3A	120.7	C16—C15—C8	118.13 (9)
C4—C3—H3A	120.7	C17—C16—C15	119.86 (11)
C5—C4—C3	118.46 (11)	C17—C16—H16A	120.1
C5—C4—H4A	120.8	C15—C16—H16A	120.1
C3—C4—H4A	120.8	C18—C17—C16	119.89 (11)
N1—C5—C4	123.02 (10)	C18—C17—H17A	120.1
N1—C5—C6	114.70 (9)	C16—C17—H17A	120.1
C4—C5—C6	122.27 (10)	C17—C18—C19	120.34 (10)
N2—C6—N4	125.06 (10)	C17—C18—H18A	119.8
N2—C6—C5	115.86 (9)	C19—C18—H18A	119.8
N4—C6—C5	118.99 (9)	C18—C19—C20	120.51 (11)
N4—C7—C8	118.81 (10)	C18—C19—H19A	119.7
N4—C7—C9	116.98 (9)	C20—C19—H19A	119.7
C8—C7—C9	124.20 (9)	C19—C20—C15	119.27 (11)
N3—C8—C7	120.57 (9)	C19—C20—H20A	120.4
N3—C8—C15	116.49 (9)	C15—C20—H20A	120.4
N2—Cu1—N1—C1	178.72 (9)	C6—N4—C7—C9	174.04 (9)
Cl2—Cu1—N1—C1	2.12 (8)	N2—N3—C8—C7	−9.00 (15)
N2—Cu1—N1—C5	0.82 (7)	N2—N3—C8—C15	168.65 (9)
Cl2—Cu1—N1—C5	−175.79 (6)	N4—C7—C8—N3	13.04 (15)
N1—Cu1—N2—C6	−1.13 (7)	C9—C7—C8—N3	−165.70 (10)
Cl1—Cu1—N2—C6	−179.79 (7)	N4—C7—C8—C15	−164.45 (9)
N1—Cu1—N2—N3	171.59 (8)	C9—C7—C8—C15	16.81 (15)
Cl1—Cu1—N2—N3	−7.06 (8)	N4—C7—C9—C14	−143.81 (10)
C6—N2—N3—C8	−2.66 (14)	C8—C7—C9—C14	34.96 (15)
Cu1—N2—N3—C8	−175.08 (7)	N4—C7—C9—C10	34.48 (14)
C5—N1—C1—C2	−0.59 (14)	C8—C7—C9—C10	−146.76 (10)
Cu1—N1—C1—C2	−178.43 (7)	C14—C9—C10—C11	−1.04 (16)
N1—C1—C2—C3	0.67 (15)	C7—C9—C10—C11	−179.37 (9)
C1—C2—C3—C4	−0.44 (15)	C9—C10—C11—C12	0.96 (16)
C2—C3—C4—C5	0.17 (16)	C10—C11—C12—C13	0.06 (17)
C1—N1—C5—C4	0.30 (15)	C11—C12—C13—C14	−1.01 (18)
Cu1—N1—C5—C4	178.40 (8)	C12—C13—C14—C9	0.91 (18)
C1—N1—C5—C6	−178.51 (9)	C10—C9—C14—C13	0.12 (17)
Cu1—N1—C5—C6	−0.41 (10)	C7—C9—C14—C13	178.39 (10)
C3—C4—C5—N1	−0.10 (16)	N3—C8—C15—C20	51.40 (14)
C3—C4—C5—C6	178.62 (9)	C7—C8—C15—C20	−131.01 (11)
N3—N2—C6—N4	11.56 (15)	N3—C8—C15—C16	−127.17 (11)
Cu1—N2—C6—N4	−175.20 (8)	C7—C8—C15—C16	50.41 (14)
N3—N2—C6—C5	−172.00 (8)	C20—C15—C16—C17	−0.26 (17)
Cu1—N2—C6—C5	1.25 (11)	C8—C15—C16—C17	178.34 (10)
C7—N4—C6—N2	−7.33 (15)	C15—C16—C17—C18	1.01 (18)
C7—N4—C6—C5	176.33 (8)	C16—C17—C18—C19	−0.67 (19)
N1—C5—C6—N2	−0.56 (13)	C17—C18—C19—C20	−0.42 (18)
C4—C5—C6—N2	−179.38 (10)	C18—C19—C20—C15	1.16 (17)
N1—C5—C6—N4	176.11 (8)	C16—C15—C20—C19	−0.81 (16)
C4—C5—C6—N4	−2.70 (15)	C8—C15—C20—C19	−179.36 (10)
C6—N4—C7—C8	−4.79 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl2	0.93	2.58	3.151 (1)	121
C2—H2A···Cl1^i	0.93	2.90	3.552 (1)	129
C12—H12A···Cl2^ii	0.93	2.83	3.522 (1)	132

Symmetry codes: (i) x, y, z+1; (ii) −x+1/4, y+1/4, z+1/4.