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In the title compound, [Cu(C9H5N4O)Cl(C12H8N2)]n or [Cu(tcnoet)Cl(phen)]n, where phen is 1,10-phenanthroline and tcnoet is 1,1,3,3-tetra­cyano-2-eth­oxy­propenide, the axially elongated (4 + 2) coordination polyhedron around the CuII centre contains N atoms from three different tcnoet ligands. The resulting coordination polymer takes the form of sheets which are linked in pairs by a single C-H...N hydrogen bond to form bilayers. The bond lengths provide evidence for significant bond fixation in the phen ligand and extensive electronic delocalization in the tcnoet ligand, where the two -C(CN)2 units are rotated, in conrotatory fashion, out of the plane of the central C3O fragment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613032804/sk3522sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613032804/sk3522Isup2.hkl
Contains datablock I

CCDC reference: 975003

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Poly[[chlorido(1,10-phenanthroline-κ2N,N')copper(II)]-µ3-1,1,3,3-tetracyano-2-ethoxypropenido-κ3N:N':N''] top
Crystal data top
[Cu(C9H5N4O)Cl(C12H8N2)]F(000) = 1880
Mr = 464.37Dx = 1.544 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6366 reflections
a = 31.79 (3) Åθ = 2.6–31.0°
b = 7.925 (6) ŵ = 1.25 mm1
c = 16.005 (13) ÅT = 296 K
β = 97.69 (3)°Plate, green
V = 3996 (6) Å30.27 × 0.23 × 0.14 mm
Z = 8
Data collection top
Bruker X8 APEXII area-detector
diffractometer
4596 independent reflections
Radiation source: fine-focus sealed tube3188 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.6°
φ and ω scansh = 4141
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1010
Tmin = 0.722, Tmax = 0.804l = 2020
34518 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.7334P]
where P = (Fo2 + 2Fc2)/3
4596 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.37 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.109132 (10)0.30029 (4)0.695410 (18)0.03960 (12)
Cl10.05105 (2)0.44903 (10)0.64741 (5)0.0578 (2)
N10.16459 (7)0.1941 (2)0.75086 (13)0.0384 (5)
C20.19716 (9)0.1342 (4)0.71602 (18)0.0504 (7)
H20.19600.13720.65770.061*
C30.23308 (9)0.0670 (4)0.7640 (2)0.0601 (8)
H30.25520.02490.73740.072*
C40.23586 (9)0.0630 (4)0.8496 (2)0.0586 (8)
H40.26000.01950.88180.070*
C4A0.20220 (8)0.1247 (3)0.88875 (17)0.0442 (6)
C4B0.16713 (8)0.1896 (3)0.83635 (15)0.0365 (5)
C50.20146 (10)0.1260 (4)0.97815 (18)0.0565 (8)
H50.22480.08491.01360.068*
C60.16767 (10)0.1857 (3)1.01196 (17)0.0526 (7)
H60.16810.18531.07020.063*
C6A0.13105 (9)0.2496 (3)0.95917 (15)0.0428 (6)
C6B0.13112 (8)0.2516 (3)0.87180 (15)0.0355 (5)
C70.09436 (10)0.3073 (3)0.98932 (17)0.0507 (7)
H70.09290.30901.04700.061*
C80.06066 (10)0.3611 (4)0.93366 (19)0.0558 (7)
H80.03590.39760.95310.067*
C90.06358 (9)0.3610 (3)0.84764 (18)0.0483 (7)
H90.04050.39880.81050.058*
N100.09806 (6)0.3090 (2)0.81664 (13)0.0370 (5)
C110.14488 (9)0.2787 (3)0.43121 (16)0.0421 (6)
C120.11597 (8)0.2046 (3)0.36808 (16)0.0411 (6)
C130.11784 (9)0.2112 (3)0.28176 (15)0.0423 (6)
C1110.13474 (9)0.2791 (3)0.51440 (17)0.0448 (6)
N1110.12696 (8)0.2807 (3)0.58229 (15)0.0523 (6)
C1120.18515 (11)0.3424 (4)0.41863 (17)0.0564 (8)
N1120.21808 (10)0.3930 (5)0.41061 (18)0.0888 (10)
O1210.08607 (6)0.1140 (3)0.39883 (12)0.0552 (5)
C1210.04102 (10)0.1324 (5)0.3638 (2)0.0801 (11)
H21A0.03770.22400.32330.096*
H21B0.03090.02940.33520.096*
C1220.01714 (14)0.1667 (7)0.4313 (4)0.130 (2)
H22A0.01180.18910.40880.196*
H22B0.02890.26340.46220.196*
H22C0.01830.07090.46820.196*
C1310.09473 (10)0.0948 (3)0.22534 (17)0.0503 (7)
N1310.07748 (10)0.0037 (3)0.18067 (17)0.0710 (8)
C1320.14346 (9)0.3290 (3)0.24406 (17)0.0450 (6)
N1320.16247 (9)0.4237 (3)0.21067 (16)0.0617 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0404 (2)0.0556 (2)0.02246 (18)0.00481 (14)0.00309 (13)0.00303 (12)
Cl10.0434 (4)0.0846 (5)0.0444 (4)0.0096 (3)0.0016 (3)0.0217 (3)
N10.0375 (12)0.0507 (11)0.0273 (11)0.0018 (9)0.0053 (9)0.0002 (9)
C20.0427 (16)0.0718 (17)0.0386 (16)0.0057 (13)0.0122 (13)0.0008 (13)
C30.0394 (16)0.084 (2)0.059 (2)0.0145 (14)0.0147 (15)0.0004 (16)
C40.0384 (16)0.080 (2)0.055 (2)0.0130 (14)0.0019 (14)0.0055 (15)
C4A0.0388 (15)0.0538 (14)0.0378 (15)0.0010 (11)0.0030 (12)0.0010 (11)
C4B0.0371 (14)0.0428 (12)0.0293 (14)0.0028 (10)0.0032 (11)0.0001 (9)
C50.0547 (19)0.0720 (18)0.0375 (17)0.0061 (15)0.0133 (14)0.0058 (13)
C60.062 (2)0.0689 (17)0.0241 (14)0.0041 (14)0.0038 (13)0.0008 (12)
C6A0.0544 (17)0.0492 (13)0.0243 (13)0.0007 (12)0.0034 (12)0.0006 (10)
C6B0.0371 (14)0.0436 (12)0.0251 (13)0.0007 (10)0.0023 (11)0.0003 (9)
C70.0625 (19)0.0647 (16)0.0267 (14)0.0034 (14)0.0128 (13)0.0029 (12)
C80.0533 (18)0.0749 (18)0.0432 (18)0.0107 (15)0.0216 (15)0.0007 (14)
C90.0416 (16)0.0652 (16)0.0393 (16)0.0104 (13)0.0097 (13)0.0023 (12)
N100.0341 (11)0.0495 (11)0.0275 (11)0.0042 (9)0.0045 (9)0.0012 (8)
C110.0451 (15)0.0578 (15)0.0235 (13)0.0059 (12)0.0053 (11)0.0010 (10)
C120.0412 (15)0.0497 (14)0.0321 (14)0.0105 (11)0.0036 (12)0.0009 (10)
C130.0506 (16)0.0495 (14)0.0255 (14)0.0084 (12)0.0003 (12)0.0033 (10)
C1110.0448 (16)0.0580 (15)0.0301 (15)0.0084 (12)0.0005 (12)0.0010 (11)
N1110.0539 (15)0.0763 (16)0.0267 (13)0.0026 (12)0.0051 (11)0.0015 (11)
C1120.061 (2)0.083 (2)0.0246 (15)0.0050 (16)0.0019 (14)0.0071 (13)
N1120.068 (2)0.153 (3)0.0455 (18)0.040 (2)0.0069 (15)0.0122 (18)
O1210.0469 (12)0.0730 (12)0.0453 (12)0.0016 (10)0.0050 (9)0.0058 (9)
C1210.046 (2)0.121 (3)0.071 (3)0.0071 (19)0.0003 (18)0.016 (2)
C1220.062 (3)0.190 (5)0.142 (5)0.014 (3)0.024 (3)0.022 (4)
C1310.0620 (19)0.0557 (15)0.0317 (15)0.0120 (13)0.0003 (14)0.0000 (12)
N1310.089 (2)0.0700 (17)0.0493 (17)0.0026 (15)0.0084 (15)0.0145 (13)
C1320.0503 (17)0.0567 (15)0.0261 (14)0.0137 (13)0.0022 (12)0.0038 (11)
N1320.0654 (17)0.0765 (17)0.0425 (15)0.0009 (14)0.0045 (13)0.0103 (13)
Geometric parameters (Å, º) top
Cu1—Cl12.2383 (16)C9—H90.9300
Cu1—N12.046 (2)N10—C6B1.358 (3)
Cu1—N102.019 (3)C6B—C4B1.431 (4)
Cu1—N1111.974 (3)C4B—N11.360 (3)
Cu1—N131i2.555 (3)C4A—C4B1.400 (4)
Cu1—N132ii2.758 (4)C6A—C6B1.399 (4)
N1—C21.328 (3)C11—C121.401 (4)
C2—C31.394 (4)C11—C1111.411 (4)
C2—H20.9300C11—C1121.416 (4)
C3—C41.362 (4)C12—O1211.337 (3)
C3—H30.9300C12—C131.392 (4)
C4—C4A1.399 (4)C13—C1311.424 (4)
C4—H40.9300C13—C1321.425 (4)
C4A—C51.434 (4)C111—N1111.146 (4)
C5—C61.351 (4)C112—N1121.144 (4)
C5—H50.9300O121—C1211.474 (4)
C6—C6A1.436 (4)C121—C1221.426 (5)
C6—H60.9300C121—H21A0.9700
C6A—C71.398 (4)C121—H21B0.9700
C7—C81.367 (4)C122—H22A0.9600
C7—H70.9300C122—H22B0.9600
C8—C91.392 (4)C122—H22C0.9600
C8—H80.9300C131—N1311.147 (4)
C9—N101.328 (3)C132—N1321.140 (4)
Cl1—Cu1—N1171.50 (6)N10—C6B—C6A123.3 (2)
Cl1—Cu1—N1094.00 (7)N10—C6B—C4B116.6 (2)
Cl1—Cu1—N11192.95 (8)C6A—C6B—C4B120.1 (2)
N1—Cu1—N1081.27 (9)C8—C7—C6A119.7 (3)
N1—Cu1—N11191.66 (10)C8—C7—H7120.2
N10—Cu1—N111172.91 (9)C6A—C7—H7120.2
N131i—Cu1—Cl198.99 (8)C7—C8—C9119.6 (3)
N131i—Cu1—N188.14 (9)C7—C8—H8120.2
N131i—Cu1—N1090.17 (8)C9—C8—H8120.2
N131i—Cu1—N11190.05 (10)N10—C9—C8122.5 (3)
N132ii—Cu1—Cl194.70 (7)N10—C9—H9118.7
N132ii—Cu1—N178.69 (8)C8—C9—H9118.7
N132ii—Cu1—N1094.13 (8)C9—N10—C6B117.8 (2)
N132ii—Cu1—N11183.98 (10)C9—N10—Cu1128.95 (18)
N131i—Cu1—N132ii165.34 (10)C6B—N10—Cu1113.20 (17)
C2—N1—C4B117.9 (2)C12—C11—C111118.1 (3)
C2—N1—Cu1129.80 (19)C12—C11—C112124.5 (2)
C4B—N1—Cu1112.27 (16)C111—C11—C112117.3 (2)
N1—C2—C3122.2 (3)O121—C12—C13120.8 (2)
N1—C2—H2118.9O121—C12—C11113.0 (2)
C3—C2—H2118.9C13—C12—C11126.1 (3)
C4—C3—C2120.1 (3)C12—C13—C131121.2 (3)
C4—C3—H3120.0C12—C13—C132123.2 (2)
C2—C3—H3120.0C131—C13—C132115.6 (2)
C3—C4—C4A119.5 (3)N111—C111—C11179.1 (3)
C3—C4—H4120.3C111—N111—Cu1174.3 (2)
C4A—C4—H4120.3N112—C112—C11178.2 (3)
C4—C4A—C4B117.1 (3)C12—O121—C121120.7 (2)
C4—C4A—C5124.4 (3)C122—C121—O121108.7 (3)
C4B—C4A—C5118.5 (2)C122—C121—H21A110.0
N1—C4B—C4A123.2 (2)O121—C121—H21A110.0
N1—C4B—C6B116.5 (2)C122—C121—H21B110.0
C4A—C4B—C6B120.3 (2)O121—C121—H21B110.0
C6—C5—C4A121.5 (3)H21A—C121—H21B108.3
C6—C5—H5119.3C121—C122—H22A109.5
C4A—C5—H5119.3C121—C122—H22B109.5
C5—C6—C6A120.9 (3)H22A—C122—H22B109.5
C5—C6—H6119.6C121—C122—H22C109.5
C6A—C6—H6119.6H22A—C122—H22C109.5
C7—C6A—C6B117.0 (2)H22B—C122—H22C109.5
C7—C6A—C6124.1 (3)N131—C131—C13177.1 (3)
C6B—C6A—C6118.8 (3)N132—C132—C13176.7 (3)
N111—Cu1—N1—C22.0 (2)C4A—C4B—C6B—N10178.6 (2)
N10—Cu1—N1—C2178.4 (2)N1—C4B—C6B—C6A179.3 (2)
N111—Cu1—N1—C4B176.87 (17)C4A—C4B—C6B—C6A0.8 (4)
N10—Cu1—N1—C4B2.66 (16)C6B—C6A—C7—C80.4 (4)
C4B—N1—C2—C30.4 (4)C6—C6A—C7—C8178.0 (3)
Cu1—N1—C2—C3179.3 (2)C6A—C7—C8—C91.2 (4)
N1—C2—C3—C40.8 (5)C7—C8—C9—N100.5 (5)
C2—C3—C4—C4A0.8 (5)C8—C9—N10—C6B1.1 (4)
C3—C4—C4A—C4B0.6 (4)C8—C9—N10—Cu1179.4 (2)
C3—C4—C4A—C5179.6 (3)C6A—C6B—N10—C92.1 (4)
C2—N1—C4B—C4A0.2 (4)C4B—C6B—N10—C9177.4 (2)
Cu1—N1—C4B—C4A179.24 (19)C6A—C6B—N10—Cu1178.4 (2)
C2—N1—C4B—C6B178.6 (2)C4B—C6B—N10—Cu12.2 (3)
Cu1—N1—C4B—C6B2.3 (3)N1—Cu1—N10—C9176.9 (2)
C4—C4A—C4B—N10.2 (4)Cl1—Cu1—N10—C910.2 (2)
C5—C4A—C4B—N1179.9 (2)N1—Cu1—N10—C6B2.62 (16)
C4—C4A—C4B—C6B178.6 (2)Cl1—Cu1—N10—C6B170.27 (16)
C5—C4A—C4B—C6B1.5 (4)C111—C11—C12—O12112.4 (3)
C4—C4A—C5—C6179.2 (3)C112—C11—C12—O121162.7 (3)
C4B—C4A—C5—C61.0 (4)C111—C11—C12—C13171.3 (2)
C4A—C5—C6—C6A0.2 (4)C112—C11—C12—C1313.6 (4)
C5—C6—C6A—C7177.5 (3)O121—C12—C13—C13114.2 (4)
C5—C6—C6A—C6B0.9 (4)C11—C12—C13—C131161.8 (3)
C7—C6A—C6B—N101.3 (4)O121—C12—C13—C132167.7 (2)
C6—C6A—C6B—N10179.8 (2)C11—C12—C13—C13216.2 (4)
C7—C6A—C6B—C4B178.1 (2)C13—C12—O121—C12150.1 (4)
C6—C6A—C6B—C4B0.4 (4)C11—C12—O121—C121133.4 (3)
N1—C4B—C6B—N100.1 (3)C12—O121—C121—C122126.9 (4)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···N112iii0.932.553.450 (6)163
Symmetry code: (iii) x+1/2, y1/2, z+3/2.
 

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