trans-Bis(2,2′-di­pyridyl­amine-κ²N,N′)­bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenido-κN)copper(II)

The title compound, [Cu(C₉H₅N₄O)₂(C₁₀H₉N₃)₂], was synthesized solvothermally. The complex exhibits a distorted octa­hedral coordination geometry. The Cu^II 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].

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.094
• Data-to-parameter ratio = 22.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         N6 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C14      --C15      .        5.2 s.u.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12A     ..N5       .       2.64 Ang.
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (I)       .       1.19 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

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)

Crystal data

[Cu(C9H5N4O)2(C10H9N3)2]	Z = 1
Mr = 776.28	F(000) = 399
Triclinic, P1	Dx = 1.403 Mg m^−3
a = 7.5101 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2232 (4) Å	Cell parameters from 937 reflections
c = 13.6405 (6) Å	θ = 2.6–28.1°
α = 99.068 (1)°	µ = 0.65 mm^−1
β = 98.864 (1)°	T = 300 K
γ = 93.139 (1)°	Block, blue
V = 918.86 (7) Å^3	0.40 × 0.10 × 0.06 mm

Data collection

Oxford Diffraction X calibur CCD diffractometer	4388 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray source	Rint = 0.062
ω scans	θmax = 30.6°, θmin = 2.5°
Absorption correction: multi-scan (CrysalisRed; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.481, Tmax = 1.000	k = −13→13
51758 measured reflections	l = −19→19
5649 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0294P)^2 + 0.4397P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5649 reflections	Δρmax = 0.32 e Å^−3
255 parameters	Δρmin = −0.44 e Å^−3
0 restraints

Special details

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 U_iso(H) = kU_eq(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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.5	0.5	0.5	0.03141 (9)
N1	0.67538 (19)	0.64977 (14)	0.59690 (10)	0.0313 (3)
N2	0.4406 (2)	0.79956 (16)	0.62884 (10)	0.0345 (3)
H2	0.413 (3)	0.872 (2)	0.6688 (16)	0.042 (5)*
N3	0.37389 (19)	0.67548 (15)	0.46127 (10)	0.0313 (3)
O1	0.33800 (19)	0.57177 (13)	0.88700 (10)	0.0459 (3)
N5	0.2377 (3)	0.4862 (2)	1.13970 (13)	0.0691 (6)
N6	0.3087 (3)	0.47360 (18)	0.63022 (12)	0.0506 (4)
N7	0.0144 (3)	0.1256 (2)	0.91228 (16)	0.0691 (6)
N8	0.3262 (3)	0.07139 (19)	0.75000 (14)	0.0630 (5)
C1	0.6156 (2)	0.76147 (16)	0.65471 (11)	0.0301 (3)
C2	0.7266 (3)	0.84429 (19)	0.73900 (13)	0.0416 (4)
H2A	0.68	0.9168	0.781	0.05*
C3	0.9045 (3)	0.8172 (2)	0.75871 (16)	0.0511 (5)
H3	0.98	0.8703	0.8148	0.061*
C4	0.9713 (3)	0.7099 (2)	0.69434 (16)	0.0487 (5)
H4	1.0934	0.6934	0.7044	0.058*
C5	0.8543 (2)	0.6287 (2)	0.61567 (14)	0.0394 (4)
H5	0.8991	0.5557	0.5731	0.047*
C6	0.3509 (2)	0.78931 (17)	0.53097 (12)	0.0318 (3)
C7	0.2986 (3)	0.6766 (2)	0.36427 (13)	0.0403 (4)
H7	0.3195	0.6006	0.315	0.048*
C8	0.1940 (3)	0.7837 (2)	0.33556 (15)	0.0506 (5)
H8	0.1454	0.7811	0.2683	0.061*
C9	0.1619 (3)	0.8964 (3)	0.40891 (17)	0.0568 (6)
H9	0.0872	0.9688	0.3918	0.068*
C10	0.2409 (3)	0.9008 (2)	0.50707 (15)	0.0482 (5)
H10	0.2217	0.9766	0.557	0.058*
C11	0.3586 (4)	0.8295 (2)	0.9359 (2)	0.0680 (7)
H11A	0.4881	0.8317	0.9499	0.102*
H11B	0.3188	0.9096	0.979	0.102*
H11C	0.321	0.839	0.8669	0.102*
C12	0.2784 (4)	0.6878 (2)	0.95455 (17)	0.0560 (6)
H12A	0.3177	0.676	1.0238	0.067*
H12B	0.1475	0.6855	0.9424	0.067*
C13	0.2780 (2)	0.43072 (17)	0.87862 (12)	0.0315 (3)
C14	0.2105 (2)	0.37033 (18)	0.95387 (12)	0.0335 (3)
C15	0.2291 (3)	0.4382 (2)	1.05654 (13)	0.0417 (4)
C16	0.2916 (2)	0.34824 (18)	0.78366 (12)	0.0344 (4)
C17	0.3030 (3)	0.42011 (19)	0.70040 (13)	0.0377 (4)
C18	0.1052 (3)	0.2327 (2)	0.92985 (13)	0.0415 (4)
C19	0.3079 (3)	0.1948 (2)	0.76699 (13)	0.0407 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.04112 (17)	0.02558 (14)	0.02394 (14)	0.00860 (11)	0.00108 (11)	−0.00461 (10)
N1	0.0365 (7)	0.0290 (6)	0.0257 (6)	0.0051 (5)	0.0044 (5)	−0.0037 (5)
N2	0.0445 (8)	0.0299 (7)	0.0270 (7)	0.0121 (6)	0.0069 (6)	−0.0056 (5)
N3	0.0402 (7)	0.0299 (6)	0.0231 (6)	0.0083 (6)	0.0039 (5)	0.0018 (5)
O1	0.0580 (8)	0.0292 (6)	0.0501 (8)	−0.0050 (6)	0.0255 (6)	−0.0082 (5)
N5	0.0958 (16)	0.0746 (14)	0.0308 (9)	−0.0078 (12)	0.0136 (9)	−0.0077 (9)
N6	0.0751 (12)	0.0427 (9)	0.0402 (9)	0.0118 (8)	0.0270 (8)	0.0065 (7)
N7	0.1046 (17)	0.0401 (10)	0.0621 (12)	−0.0155 (10)	0.0345 (12)	−0.0062 (9)
N8	0.1070 (16)	0.0381 (9)	0.0497 (10)	0.0243 (10)	0.0317 (11)	0.0004 (8)
C1	0.0411 (9)	0.0237 (7)	0.0246 (7)	0.0038 (6)	0.0062 (6)	0.0004 (6)
C2	0.0569 (11)	0.0287 (8)	0.0331 (9)	0.0042 (8)	0.0005 (8)	−0.0069 (7)
C3	0.0535 (12)	0.0390 (10)	0.0490 (11)	−0.0008 (9)	−0.0125 (9)	−0.0061 (8)
C4	0.0383 (10)	0.0434 (10)	0.0579 (12)	0.0025 (8)	−0.0034 (9)	0.0004 (9)
C5	0.0378 (9)	0.0376 (9)	0.0411 (9)	0.0069 (7)	0.0072 (7)	−0.0004 (7)
C6	0.0370 (8)	0.0295 (8)	0.0297 (8)	0.0084 (6)	0.0080 (6)	0.0029 (6)
C7	0.0500 (10)	0.0451 (10)	0.0246 (8)	0.0065 (8)	0.0035 (7)	0.0037 (7)
C8	0.0548 (12)	0.0627 (13)	0.0359 (10)	0.0155 (10)	0.0006 (9)	0.0162 (9)
C9	0.0601 (13)	0.0600 (13)	0.0559 (13)	0.0299 (11)	0.0059 (10)	0.0221 (10)
C10	0.0575 (12)	0.0427 (10)	0.0474 (11)	0.0248 (9)	0.0119 (9)	0.0064 (8)
C11	0.0748 (16)	0.0323 (10)	0.0917 (19)	−0.0020 (10)	0.0112 (14)	−0.0005 (11)
C12	0.0835 (16)	0.0299 (9)	0.0549 (12)	0.0032 (9)	0.0289 (11)	−0.0086 (8)
C13	0.0350 (8)	0.0281 (7)	0.0295 (8)	0.0034 (6)	0.0076 (6)	−0.0030 (6)
C14	0.0420 (9)	0.0317 (8)	0.0255 (7)	0.0056 (7)	0.0072 (7)	−0.0017 (6)
C15	0.0478 (10)	0.0447 (10)	0.0307 (9)	0.0008 (8)	0.0082 (8)	0.0005 (7)
C16	0.0458 (10)	0.0290 (8)	0.0298 (8)	0.0060 (7)	0.0140 (7)	0.0003 (6)
C17	0.0495 (10)	0.0309 (8)	0.0349 (9)	0.0077 (7)	0.0183 (8)	−0.0010 (7)
C18	0.0612 (12)	0.0335 (9)	0.0317 (9)	0.0058 (8)	0.0172 (8)	0.0009 (7)
C19	0.0586 (11)	0.0349 (9)	0.0308 (8)	0.0107 (8)	0.0166 (8)	0.0004 (7)

Geometric parameters (Å, º)

Cu1—N1	2.0196 (13)	C4—C5	1.367 (3)
Cu1—N1^i	2.0196 (13)	C4—H4	0.93
Cu1—N3^i	2.0196 (13)	C5—H5	0.93
Cu1—N3	2.0196 (13)	C6—C10	1.400 (2)
Cu1—N6^i	2.4828 (16)	C7—C8	1.363 (3)
Cu1—N6	2.4828 (16)	C7—H7	0.93
N1—C1	1.3374 (19)	C8—C9	1.383 (3)
N1—C5	1.359 (2)	C8—H8	0.93
N2—C6	1.386 (2)	C9—C10	1.372 (3)
N2—C1	1.386 (2)	C9—H9	0.93
N2—H2	0.85 (2)	C10—H10	0.93
N3—C6	1.339 (2)	C11—C12	1.484 (3)
N3—C7	1.358 (2)	C11—H11A	0.96
O1—C13	1.335 (2)	C11—H11B	0.96
O1—C12	1.436 (2)	C11—H11C	0.96
N5—C15	1.142 (2)	C12—H12A	0.97
N6—C17	1.149 (2)	C12—H12B	0.97
N7—C18	1.140 (3)	C13—C14	1.389 (2)
N8—C19	1.145 (2)	C13—C16	1.416 (2)
C1—C2	1.400 (2)	C14—C18	1.422 (2)
C2—C3	1.366 (3)	C14—C15	1.423 (2)
C2—H2A	0.93	C16—C19	1.413 (2)
C3—C4	1.385 (3)	C16—C17	1.413 (2)
C3—H3	0.93
N1—Cu1—N1^i	180.0	N3—C6—N2	119.59 (14)
N1—Cu1—N3^i	94.54 (5)	N3—C6—C10	121.57 (16)
N1^i—Cu1—N3^i	85.46 (5)	N2—C6—C10	118.82 (15)
N1—Cu1—N3	85.46 (5)	N3—C7—C8	123.29 (17)
N1^i—Cu1—N3	94.54 (5)	N3—C7—H7	118.4
N3^i—Cu1—N3	180.00 (7)	C8—C7—H7	118.4
N1—Cu1—N6^i	88.19 (6)	C7—C8—C9	118.40 (18)
N1^i—Cu1—N6^i	91.82 (6)	C7—C8—H8	120.8
N3^i—Cu1—N6^i	92.15 (6)	C9—C8—H8	120.8
N3—Cu1—N6^i	87.85 (6)	C10—C9—C8	119.61 (18)
N1—Cu1—N6	91.81 (6)	C10—C9—H9	120.2
N1^i—Cu1—N6	88.18 (6)	C8—C9—H9	120.2
N3^i—Cu1—N6	87.85 (6)	C9—C10—C6	119.00 (18)
N3—Cu1—N6	92.15 (6)	C9—C10—H10	120.5
N6^i—Cu1—N6	180.0	C6—C10—H10	120.5
C1—N1—C5	117.73 (14)	C12—C11—H11A	109.5
C1—N1—Cu1	120.69 (11)	C12—C11—H11B	109.5
C5—N1—Cu1	120.93 (11)	H11A—C11—H11B	109.5
C6—N2—C1	124.60 (14)	C12—C11—H11C	109.5
C6—N2—H2	113.2 (14)	H11A—C11—H11C	109.5
C1—N2—H2	113.6 (14)	H11B—C11—H11C	109.5
C6—N3—C7	117.92 (14)	O1—C12—C11	107.53 (18)
C6—N3—Cu1	121.18 (11)	O1—C12—H12A	110.2
C7—N3—Cu1	120.73 (11)	C11—C12—H12A	110.2
C13—O1—C12	122.75 (14)	O1—C12—H12B	110.2
C17—N6—Cu1	141.76 (15)	C11—C12—H12B	110.2
N1—C1—N2	119.24 (14)	H12A—C12—H12B	108.5
N1—C1—C2	121.84 (16)	O1—C13—C14	124.44 (14)
N2—C1—C2	118.89 (14)	O1—C13—C16	112.14 (15)
C3—C2—C1	119.08 (17)	C14—C13—C16	123.42 (15)
C3—C2—H2A	120.5	C13—C14—C18	120.00 (15)
C1—C2—H2A	120.5	C13—C14—C15	125.50 (16)
C2—C3—C4	119.39 (17)	C18—C14—C15	114.42 (16)
C2—C3—H3	120.3	N5—C15—C14	176.1 (2)
C4—C3—H3	120.3	C19—C16—C17	115.91 (14)
C5—C4—C3	118.66 (18)	C19—C16—C13	123.65 (16)
C5—C4—H4	120.7	C17—C16—C13	120.29 (15)
C3—C4—H4	120.7	N6—C17—C16	177.3 (2)
N1—C5—C4	122.93 (17)	N7—C18—C14	176.8 (2)
N1—C5—H5	118.5	N8—C19—C16	176.7 (2)
C4—C5—H5	118.5
C5—N1—C1—N2	170.75 (15)	C6—N3—C7—C8	−3.4 (3)
Cu1—N1—C1—N2	−18.4 (2)	Cu1—N3—C7—C8	172.08 (16)
C5—N1—C1—C2	−7.2 (2)	N3—C7—C8—C9	−0.4 (3)
Cu1—N1—C1—C2	163.65 (13)	C7—C8—C9—C10	2.5 (4)
C6—N2—C1—N1	−33.7 (2)	C8—C9—C10—C6	−0.8 (3)
C6—N2—C1—C2	144.31 (17)	N3—C6—C10—C9	−3.1 (3)
N1—C1—C2—C3	4.7 (3)	N2—C6—C10—C9	175.5 (2)
N2—C1—C2—C3	−173.20 (18)	C13—O1—C12—C11	−174.33 (19)
C1—C2—C3—C4	0.8 (3)	C12—O1—C13—C14	−25.1 (3)
C2—C3—C4—C5	−3.5 (3)	C12—O1—C13—C16	155.17 (18)
C1—N1—C5—C4	4.4 (3)	O1—C13—C14—C18	162.61 (17)
Cu1—N1—C5—C4	−166.43 (16)	C16—C13—C14—C18	−17.7 (3)
C3—C4—C5—N1	0.9 (3)	O1—C13—C14—C15	−14.0 (3)
C7—N3—C6—N2	−173.51 (16)	C16—C13—C14—C15	165.63 (18)
Cu1—N3—C6—N2	11.1 (2)	O1—C13—C16—C19	153.95 (18)
C7—N3—C6—C10	5.1 (3)	C14—C13—C16—C19	−25.7 (3)
Cu1—N3—C6—C10	−170.32 (15)	O1—C13—C16—C17	−21.4 (2)
C1—N2—C6—N3	37.9 (2)	C14—C13—C16—C17	158.95 (18)
C1—N2—C6—C10	−140.78 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N8^ii	0.85 (2)	2.18 (2)	3.020 (2)	171.2 (19)
C7—H7···N5^iii	0.93	2.43	3.234 (2)	145
C10—H10···N8^ii	0.93	2.62	3.385 (3)	140
C12—H12A···N5	0.97	2.64	3.404 (3)	136

Symmetry codes: (ii) x, y+1, z; (iii) x, y, z−1.