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The title compound, [Cu(C9H5N4O)2(C10H9N3)2], was synthesized solvothermally. The complex exhibits a distorted octa­hedral coordination geometry. The CuII atom is located on an inversion centre. The distorted octahedral CuN6 coordination sphere is composed of bidentate 2,2′-dipyrid­ylamine in the equatorial sites while the axial sites are occupied by 1,1,3,3-tetra­cyano-2-eth­oxy­propenide ligands. In the crystal, N—H...N hydrogen bonding results in chains parallel to [010].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314622011804/bt4129sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314622011804/bt4129Isup2.hkl
Contains datablock I

CCDC reference: 2225624

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020), Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

trans-Bis(2,2'-dipyridylamine-κ2N,N')bis(1,1,3,3-tetracyano-2-ethoxypropenido-κN)copper(II) top
Crystal data top
[Cu(C9H5N4O)2(C10H9N3)2]Z = 1
Mr = 776.28F(000) = 399
Triclinic, P1Dx = 1.403 Mg m3
a = 7.5101 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2232 (4) ÅCell parameters from 937 reflections
c = 13.6405 (6) Åθ = 2.6–28.1°
α = 99.068 (1)°µ = 0.65 mm1
β = 98.864 (1)°T = 300 K
γ = 93.139 (1)°Block, blue
V = 918.86 (7) Å30.40 × 0.10 × 0.06 mm
Data collection top
Oxford Diffraction X calibur CCD
diffractometer
4388 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray sourceRint = 0.062
ω scansθmax = 30.6°, θmin = 2.5°
Absorption correction: multi-scan
(CrysalisRed; Oxford Diffraction, 2009)
h = 1010
Tmin = 0.481, Tmax = 1.000k = 1313
51758 measured reflectionsl = 1919
5649 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0294P)2 + 0.4397P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5649 reflectionsΔρmax = 0.32 e Å3
255 parametersΔρmin = 0.44 e Å3
0 restraints
Special details top

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

Refinement. All hydrogen atoms bonded to C atoms were positioned geometrically and treated as riding atoms, using C—H = 0.93 Å (aromatic), 0.96 Å (CH3) or 0.97 Å (CH2), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups and 1.2 for all other H atoms bonded to C atoms. The H atom bonded to the amine N atom was refined freely, including its isotropic displacement parameter.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.50.50.50.03141 (9)
N10.67538 (19)0.64977 (14)0.59690 (10)0.0313 (3)
N20.4406 (2)0.79956 (16)0.62884 (10)0.0345 (3)
H20.413 (3)0.872 (2)0.6688 (16)0.042 (5)*
N30.37389 (19)0.67548 (15)0.46127 (10)0.0313 (3)
O10.33800 (19)0.57177 (13)0.88700 (10)0.0459 (3)
N50.2377 (3)0.4862 (2)1.13970 (13)0.0691 (6)
N60.3087 (3)0.47360 (18)0.63022 (12)0.0506 (4)
N70.0144 (3)0.1256 (2)0.91228 (16)0.0691 (6)
N80.3262 (3)0.07139 (19)0.75000 (14)0.0630 (5)
C10.6156 (2)0.76147 (16)0.65471 (11)0.0301 (3)
C20.7266 (3)0.84429 (19)0.73900 (13)0.0416 (4)
H2A0.680.91680.7810.05*
C30.9045 (3)0.8172 (2)0.75871 (16)0.0511 (5)
H30.980.87030.81480.061*
C40.9713 (3)0.7099 (2)0.69434 (16)0.0487 (5)
H41.09340.69340.70440.058*
C50.8543 (2)0.6287 (2)0.61567 (14)0.0394 (4)
H50.89910.55570.57310.047*
C60.3509 (2)0.78931 (17)0.53097 (12)0.0318 (3)
C70.2986 (3)0.6766 (2)0.36427 (13)0.0403 (4)
H70.31950.60060.3150.048*
C80.1940 (3)0.7837 (2)0.33556 (15)0.0506 (5)
H80.14540.78110.26830.061*
C90.1619 (3)0.8964 (3)0.40891 (17)0.0568 (6)
H90.08720.96880.39180.068*
C100.2409 (3)0.9008 (2)0.50707 (15)0.0482 (5)
H100.22170.97660.5570.058*
C110.3586 (4)0.8295 (2)0.9359 (2)0.0680 (7)
H11A0.48810.83170.94990.102*
H11B0.31880.90960.9790.102*
H11C0.3210.8390.86690.102*
C120.2784 (4)0.6878 (2)0.95455 (17)0.0560 (6)
H12A0.31770.6761.02380.067*
H12B0.14750.68550.94240.067*
C130.2780 (2)0.43072 (17)0.87862 (12)0.0315 (3)
C140.2105 (2)0.37033 (18)0.95387 (12)0.0335 (3)
C150.2291 (3)0.4382 (2)1.05654 (13)0.0417 (4)
C160.2916 (2)0.34824 (18)0.78366 (12)0.0344 (4)
C170.3030 (3)0.42011 (19)0.70040 (13)0.0377 (4)
C180.1052 (3)0.2327 (2)0.92985 (13)0.0415 (4)
C190.3079 (3)0.1948 (2)0.76699 (13)0.0407 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.04112 (17)0.02558 (14)0.02394 (14)0.00860 (11)0.00108 (11)0.00461 (10)
N10.0365 (7)0.0290 (6)0.0257 (6)0.0051 (5)0.0044 (5)0.0037 (5)
N20.0445 (8)0.0299 (7)0.0270 (7)0.0121 (6)0.0069 (6)0.0056 (5)
N30.0402 (7)0.0299 (6)0.0231 (6)0.0083 (6)0.0039 (5)0.0018 (5)
O10.0580 (8)0.0292 (6)0.0501 (8)0.0050 (6)0.0255 (6)0.0082 (5)
N50.0958 (16)0.0746 (14)0.0308 (9)0.0078 (12)0.0136 (9)0.0077 (9)
N60.0751 (12)0.0427 (9)0.0402 (9)0.0118 (8)0.0270 (8)0.0065 (7)
N70.1046 (17)0.0401 (10)0.0621 (12)0.0155 (10)0.0345 (12)0.0062 (9)
N80.1070 (16)0.0381 (9)0.0497 (10)0.0243 (10)0.0317 (11)0.0004 (8)
C10.0411 (9)0.0237 (7)0.0246 (7)0.0038 (6)0.0062 (6)0.0004 (6)
C20.0569 (11)0.0287 (8)0.0331 (9)0.0042 (8)0.0005 (8)0.0069 (7)
C30.0535 (12)0.0390 (10)0.0490 (11)0.0008 (9)0.0125 (9)0.0061 (8)
C40.0383 (10)0.0434 (10)0.0579 (12)0.0025 (8)0.0034 (9)0.0004 (9)
C50.0378 (9)0.0376 (9)0.0411 (9)0.0069 (7)0.0072 (7)0.0004 (7)
C60.0370 (8)0.0295 (8)0.0297 (8)0.0084 (6)0.0080 (6)0.0029 (6)
C70.0500 (10)0.0451 (10)0.0246 (8)0.0065 (8)0.0035 (7)0.0037 (7)
C80.0548 (12)0.0627 (13)0.0359 (10)0.0155 (10)0.0006 (9)0.0162 (9)
C90.0601 (13)0.0600 (13)0.0559 (13)0.0299 (11)0.0059 (10)0.0221 (10)
C100.0575 (12)0.0427 (10)0.0474 (11)0.0248 (9)0.0119 (9)0.0064 (8)
C110.0748 (16)0.0323 (10)0.0917 (19)0.0020 (10)0.0112 (14)0.0005 (11)
C120.0835 (16)0.0299 (9)0.0549 (12)0.0032 (9)0.0289 (11)0.0086 (8)
C130.0350 (8)0.0281 (7)0.0295 (8)0.0034 (6)0.0076 (6)0.0030 (6)
C140.0420 (9)0.0317 (8)0.0255 (7)0.0056 (7)0.0072 (7)0.0017 (6)
C150.0478 (10)0.0447 (10)0.0307 (9)0.0008 (8)0.0082 (8)0.0005 (7)
C160.0458 (10)0.0290 (8)0.0298 (8)0.0060 (7)0.0140 (7)0.0003 (6)
C170.0495 (10)0.0309 (8)0.0349 (9)0.0077 (7)0.0183 (8)0.0010 (7)
C180.0612 (12)0.0335 (9)0.0317 (9)0.0058 (8)0.0172 (8)0.0009 (7)
C190.0586 (11)0.0349 (9)0.0308 (8)0.0107 (8)0.0166 (8)0.0004 (7)
Geometric parameters (Å, º) top
Cu1—N12.0196 (13)C4—C51.367 (3)
Cu1—N1i2.0196 (13)C4—H40.93
Cu1—N3i2.0196 (13)C5—H50.93
Cu1—N32.0196 (13)C6—C101.400 (2)
Cu1—N6i2.4828 (16)C7—C81.363 (3)
Cu1—N62.4828 (16)C7—H70.93
N1—C11.3374 (19)C8—C91.383 (3)
N1—C51.359 (2)C8—H80.93
N2—C61.386 (2)C9—C101.372 (3)
N2—C11.386 (2)C9—H90.93
N2—H20.85 (2)C10—H100.93
N3—C61.339 (2)C11—C121.484 (3)
N3—C71.358 (2)C11—H11A0.96
O1—C131.335 (2)C11—H11B0.96
O1—C121.436 (2)C11—H11C0.96
N5—C151.142 (2)C12—H12A0.97
N6—C171.149 (2)C12—H12B0.97
N7—C181.140 (3)C13—C141.389 (2)
N8—C191.145 (2)C13—C161.416 (2)
C1—C21.400 (2)C14—C181.422 (2)
C2—C31.366 (3)C14—C151.423 (2)
C2—H2A0.93C16—C191.413 (2)
C3—C41.385 (3)C16—C171.413 (2)
C3—H30.93
N1—Cu1—N1i180.0N3—C6—N2119.59 (14)
N1—Cu1—N3i94.54 (5)N3—C6—C10121.57 (16)
N1i—Cu1—N3i85.46 (5)N2—C6—C10118.82 (15)
N1—Cu1—N385.46 (5)N3—C7—C8123.29 (17)
N1i—Cu1—N394.54 (5)N3—C7—H7118.4
N3i—Cu1—N3180.00 (7)C8—C7—H7118.4
N1—Cu1—N6i88.19 (6)C7—C8—C9118.40 (18)
N1i—Cu1—N6i91.82 (6)C7—C8—H8120.8
N3i—Cu1—N6i92.15 (6)C9—C8—H8120.8
N3—Cu1—N6i87.85 (6)C10—C9—C8119.61 (18)
N1—Cu1—N691.81 (6)C10—C9—H9120.2
N1i—Cu1—N688.18 (6)C8—C9—H9120.2
N3i—Cu1—N687.85 (6)C9—C10—C6119.00 (18)
N3—Cu1—N692.15 (6)C9—C10—H10120.5
N6i—Cu1—N6180.0C6—C10—H10120.5
C1—N1—C5117.73 (14)C12—C11—H11A109.5
C1—N1—Cu1120.69 (11)C12—C11—H11B109.5
C5—N1—Cu1120.93 (11)H11A—C11—H11B109.5
C6—N2—C1124.60 (14)C12—C11—H11C109.5
C6—N2—H2113.2 (14)H11A—C11—H11C109.5
C1—N2—H2113.6 (14)H11B—C11—H11C109.5
C6—N3—C7117.92 (14)O1—C12—C11107.53 (18)
C6—N3—Cu1121.18 (11)O1—C12—H12A110.2
C7—N3—Cu1120.73 (11)C11—C12—H12A110.2
C13—O1—C12122.75 (14)O1—C12—H12B110.2
C17—N6—Cu1141.76 (15)C11—C12—H12B110.2
N1—C1—N2119.24 (14)H12A—C12—H12B108.5
N1—C1—C2121.84 (16)O1—C13—C14124.44 (14)
N2—C1—C2118.89 (14)O1—C13—C16112.14 (15)
C3—C2—C1119.08 (17)C14—C13—C16123.42 (15)
C3—C2—H2A120.5C13—C14—C18120.00 (15)
C1—C2—H2A120.5C13—C14—C15125.50 (16)
C2—C3—C4119.39 (17)C18—C14—C15114.42 (16)
C2—C3—H3120.3N5—C15—C14176.1 (2)
C4—C3—H3120.3C19—C16—C17115.91 (14)
C5—C4—C3118.66 (18)C19—C16—C13123.65 (16)
C5—C4—H4120.7C17—C16—C13120.29 (15)
C3—C4—H4120.7N6—C17—C16177.3 (2)
N1—C5—C4122.93 (17)N7—C18—C14176.8 (2)
N1—C5—H5118.5N8—C19—C16176.7 (2)
C4—C5—H5118.5
C5—N1—C1—N2170.75 (15)C6—N3—C7—C83.4 (3)
Cu1—N1—C1—N218.4 (2)Cu1—N3—C7—C8172.08 (16)
C5—N1—C1—C27.2 (2)N3—C7—C8—C90.4 (3)
Cu1—N1—C1—C2163.65 (13)C7—C8—C9—C102.5 (4)
C6—N2—C1—N133.7 (2)C8—C9—C10—C60.8 (3)
C6—N2—C1—C2144.31 (17)N3—C6—C10—C93.1 (3)
N1—C1—C2—C34.7 (3)N2—C6—C10—C9175.5 (2)
N2—C1—C2—C3173.20 (18)C13—O1—C12—C11174.33 (19)
C1—C2—C3—C40.8 (3)C12—O1—C13—C1425.1 (3)
C2—C3—C4—C53.5 (3)C12—O1—C13—C16155.17 (18)
C1—N1—C5—C44.4 (3)O1—C13—C14—C18162.61 (17)
Cu1—N1—C5—C4166.43 (16)C16—C13—C14—C1817.7 (3)
C3—C4—C5—N10.9 (3)O1—C13—C14—C1514.0 (3)
C7—N3—C6—N2173.51 (16)C16—C13—C14—C15165.63 (18)
Cu1—N3—C6—N211.1 (2)O1—C13—C16—C19153.95 (18)
C7—N3—C6—C105.1 (3)C14—C13—C16—C1925.7 (3)
Cu1—N3—C6—C10170.32 (15)O1—C13—C16—C1721.4 (2)
C1—N2—C6—N337.9 (2)C14—C13—C16—C17158.95 (18)
C1—N2—C6—C10140.78 (18)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N8ii0.85 (2)2.18 (2)3.020 (2)171.2 (19)
C7—H7···N5iii0.932.433.234 (2)145
C10—H10···N8ii0.932.623.385 (3)140
C12—H12A···N50.972.643.404 (3)136
Symmetry codes: (ii) x, y+1, z; (iii) x, y, z1.
 

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