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In the title centrosymmetric complex, [Cu(C2N3)2(C8H7N3O)2], the CuII atom is coordinated by two N atoms from two 4-(1,2,4-triazol-1-yl)phenol ligands and two N atoms from two dicyanamide anions, adopting a very slightly distorted square-planar geometry. In the crystal structure, inter­molecular O—H...N hydrogen bonds and π–π stacking inter­actions link discrete mononuclear units into a two-dimensional network. In addition, there are three weak intra­molecular C—H...N hydrogen-bond inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051336/lh2259sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051336/lh2259Isup2.hkl
Contains datablock I

CCDC reference: 633915

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.074
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.32
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX" (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg & Berndt, 1999).

Bis(dicyanamido-κN1)bis[4-(1,2,4-triazol-1-yl)phenol-κN4]copper(II) top
Crystal data top
[Cu(C2N3)2(C8H7N3O)2]F(000) = 526
Mr = 517.98Dx = 1.680 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2647 reflections
a = 12.9515 (17) Åθ = 3.1–27.7°
b = 7.696 (1) ŵ = 1.12 mm1
c = 10.3232 (14) ÅT = 294 K
β = 95.548 (2)°Block, blue
V = 1024.1 (2) Å30.24 × 0.23 × 0.22 mm
Z = 2
Data collection top
Bruker APEX-II CCD
diffractometer
1801 independent reflections
Radiation source: fine-focus sealed tube1537 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1415
Tmin = 0.772, Tmax = 0.782k = 99
5375 measured reflectionsl = 812
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.039P)2 + 0.4336P]
where P = (Fo2 + 2Fc2)/3
1801 reflections(Δ/σ)max < 0.001
161 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

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
Cu10.50000.00000.00000.03856 (15)
O10.22165 (11)0.2162 (2)0.20100 (16)0.0457 (4)
H10.23780.15170.26290.068*
N10.19321 (11)0.1503 (2)0.01241 (15)0.0275 (4)
N20.22549 (13)0.2187 (3)0.10702 (17)0.0407 (5)
N30.35773 (12)0.0897 (2)0.01965 (16)0.0324 (4)
N40.54428 (13)0.0728 (3)0.18080 (18)0.0476 (5)
N50.56265 (14)0.1661 (3)0.40782 (17)0.0459 (5)
N60.68871 (18)0.0517 (3)0.5811 (2)0.0593 (6)
C10.32382 (16)0.1780 (3)0.1207 (2)0.0411 (5)
H1A0.36730.20750.19440.049*
C20.27213 (14)0.0746 (3)0.06212 (19)0.0330 (5)
H20.26840.01900.14240.040*
C30.08631 (14)0.1638 (2)0.06356 (18)0.0254 (4)
C40.04785 (15)0.0628 (3)0.16729 (19)0.0315 (4)
H40.09120.01410.20560.038*
C50.05575 (15)0.0763 (3)0.21430 (19)0.0324 (4)
H50.08210.00790.28410.039*
C60.11979 (14)0.1907 (3)0.15784 (19)0.0291 (4)
C70.08097 (15)0.2893 (3)0.0520 (2)0.0345 (5)
H70.12440.36470.01240.041*
C80.02237 (15)0.2758 (3)0.00503 (19)0.0329 (5)
H80.04860.34230.06590.039*
C90.55701 (15)0.1108 (3)0.2889 (2)0.0387 (5)
C100.63196 (16)0.1004 (3)0.4969 (2)0.0418 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0206 (2)0.0685 (3)0.0253 (2)0.00795 (17)0.00440 (13)0.01042 (18)
O10.0255 (7)0.0616 (11)0.0472 (10)0.0075 (7)0.0098 (7)0.0105 (8)
N10.0220 (8)0.0336 (9)0.0266 (8)0.0001 (7)0.0001 (7)0.0003 (7)
N20.0283 (9)0.0572 (12)0.0352 (10)0.0041 (8)0.0043 (8)0.0156 (9)
N30.0228 (8)0.0456 (10)0.0284 (9)0.0014 (7)0.0004 (7)0.0017 (8)
N40.0268 (9)0.0838 (15)0.0301 (10)0.0107 (9)0.0071 (8)0.0105 (10)
N50.0323 (10)0.0770 (14)0.0275 (10)0.0057 (9)0.0024 (8)0.0085 (9)
N60.0509 (13)0.0878 (17)0.0361 (12)0.0008 (12)0.0124 (10)0.0005 (11)
C10.0276 (11)0.0583 (15)0.0361 (12)0.0031 (10)0.0042 (9)0.0135 (11)
C20.0223 (10)0.0478 (12)0.0282 (10)0.0037 (9)0.0013 (8)0.0041 (9)
C30.0204 (9)0.0290 (10)0.0264 (10)0.0001 (7)0.0007 (8)0.0048 (8)
C40.0284 (10)0.0349 (11)0.0315 (11)0.0042 (8)0.0046 (8)0.0036 (9)
C50.0319 (11)0.0371 (11)0.0269 (10)0.0019 (9)0.0026 (8)0.0033 (9)
C60.0219 (9)0.0359 (11)0.0287 (10)0.0001 (8)0.0021 (8)0.0064 (8)
C70.0266 (10)0.0406 (12)0.0360 (11)0.0074 (9)0.0020 (9)0.0056 (9)
C80.0286 (11)0.0395 (12)0.0300 (11)0.0005 (8)0.0004 (9)0.0078 (9)
C90.0187 (10)0.0617 (15)0.0344 (13)0.0034 (9)0.0041 (8)0.0028 (11)
C100.0328 (11)0.0620 (15)0.0304 (12)0.0063 (11)0.0016 (10)0.0106 (11)
Geometric parameters (Å, º) top
Cu1—N41.9797 (19)N5—C101.322 (3)
Cu1—N4i1.9797 (19)N6—C101.145 (3)
Cu1—N3i1.9964 (16)C1—H1A0.9300
Cu1—N31.9964 (16)C2—H20.9300
O1—C61.365 (2)C3—C81.375 (3)
O1—H10.8200C3—C41.377 (3)
N1—C21.322 (2)C4—C51.386 (3)
N1—N21.368 (2)C4—H40.9300
N1—C31.437 (2)C5—C61.377 (3)
N2—C11.306 (3)C5—H50.9300
N3—C21.332 (2)C6—C71.385 (3)
N3—C11.353 (3)C7—C81.383 (3)
N4—C91.150 (3)C7—H70.9300
N5—C91.294 (3)C8—H80.9300
N4—Cu1—N4i180N3—C2—H2125.0
N4—Cu1—N3i90.43 (7)C8—C3—C4120.51 (18)
N4i—Cu1—N3i89.57 (7)C8—C3—N1118.93 (17)
N4—Cu1—N389.57 (7)C4—C3—N1120.55 (17)
N4i—Cu1—N390.43 (7)C3—C4—C5119.69 (19)
N3i—Cu1—N3180C3—C4—H4120.2
C6—O1—H1109.5C5—C4—H4120.2
C2—N1—N2109.80 (15)C6—C5—C4120.13 (19)
C2—N1—C3129.99 (16)C6—C5—H5119.9
N2—N1—C3120.19 (15)C4—C5—H5119.9
C1—N2—N1102.40 (17)O1—C6—C5123.79 (18)
C2—N3—C1102.70 (16)O1—C6—C7116.40 (18)
C2—N3—Cu1128.70 (14)C5—C6—C7119.80 (18)
C1—N3—Cu1128.58 (14)C8—C7—C6120.05 (18)
C9—N4—Cu1171.15 (18)C8—C7—H7120.0
C9—N5—C10120.4 (2)C6—C7—H7120.0
N2—C1—N3115.04 (19)C3—C8—C7119.79 (18)
N2—C1—H1A122.5C3—C8—H8120.1
N3—C1—H1A122.5C7—C8—H8120.1
N1—C2—N3110.06 (17)N4—C9—N5173.4 (2)
N1—C2—H2125.0N6—C10—N5174.6 (3)
C2—N1—N2—C10.1 (2)N2—N1—C3—C813.5 (3)
C3—N1—N2—C1178.50 (18)C2—N1—C3—C413.4 (3)
N4—Cu1—N3—C2172.9 (2)N2—N1—C3—C4164.82 (18)
N4i—Cu1—N3—C27.1 (2)C8—C3—C4—C51.0 (3)
N4—Cu1—N3—C15.6 (2)N1—C3—C4—C5179.28 (18)
N4i—Cu1—N3—C1174.4 (2)C3—C4—C5—C60.3 (3)
N1—N2—C1—N30.3 (3)C4—C5—C6—O1177.67 (19)
C2—N3—C1—N20.4 (3)C4—C5—C6—C71.5 (3)
Cu1—N3—C1—N2179.22 (16)O1—C6—C7—C8177.75 (19)
N2—N1—C2—N30.2 (2)C5—C6—C7—C81.5 (3)
C3—N1—C2—N3178.57 (18)C4—C3—C8—C71.0 (3)
C1—N3—C2—N10.4 (2)N1—C3—C8—C7179.32 (18)
Cu1—N3—C2—N1179.15 (13)C6—C7—C8—C30.2 (3)
C2—N1—C3—C8168.3 (2)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N20.932.482.804 (3)101
C1—H1A···N40.932.532.975 (3)110
O1—H1···N6ii0.821.952.740 (3)162
C2—H2···N4i0.932.593.001 (3)107
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z1.
 

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