Bis(dicyanamido-κN¹)bis­[4-(1,2,4-triazol-1-yl)phenol-κN⁴]copper(II)

In the title centrosymmetric complex, [Cu(C₂N₃)₂(C₈H₇N₃O)₂], the Cu^II 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.

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

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Computing details

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)

Crystal data

[Cu(C2N3)2(C8H7N3O)2]	F(000) = 526
Mr = 517.98	Dx = 1.680 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2647 reflections
a = 12.9515 (17) Å	θ = 3.1–27.7°
b = 7.696 (1) Å	µ = 1.12 mm^−1
c = 10.3232 (14) Å	T = 294 K
β = 95.548 (2)°	Block, blue
V = 1024.1 (2) Å^3	0.24 × 0.23 × 0.22 mm
Z = 2

Data collection

Bruker APEX-II CCD diffractometer	1801 independent reflections
Radiation source: fine-focus sealed tube	1537 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
Tmin = 0.772, Tmax = 0.782	k = −9→9
5375 measured reflections	l = −8→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.4336P] where P = (Fo^2 + 2Fc^2)/3
1801 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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	0.5000	0.0000	0.0000	0.03856 (15)
O1	−0.22165 (11)	0.2162 (2)	−0.20100 (16)	0.0457 (4)
H1	−0.2378	0.1517	−0.2629	0.068*
N1	0.19321 (11)	0.1503 (2)	−0.01241 (15)	0.0275 (4)
N2	0.22549 (13)	0.2187 (3)	0.10702 (17)	0.0407 (5)
N3	0.35773 (12)	0.0897 (2)	0.01965 (16)	0.0324 (4)
N4	0.54428 (13)	0.0728 (3)	0.18080 (18)	0.0476 (5)
N5	0.56265 (14)	0.1661 (3)	0.40782 (17)	0.0459 (5)
N6	0.68871 (18)	0.0517 (3)	0.5811 (2)	0.0593 (6)
C1	0.32382 (16)	0.1780 (3)	0.1207 (2)	0.0411 (5)
H1A	0.3673	0.2075	0.1944	0.049*
C2	0.27213 (14)	0.0746 (3)	−0.06212 (19)	0.0330 (5)
H2	0.2684	0.0190	−0.1424	0.040*
C3	0.08631 (14)	0.1638 (2)	−0.06356 (18)	0.0254 (4)
C4	0.04785 (15)	0.0628 (3)	−0.16729 (19)	0.0315 (4)
H4	0.0912	−0.0141	−0.2056	0.038*
C5	−0.05575 (15)	0.0763 (3)	−0.21430 (19)	0.0324 (4)
H5	−0.0821	0.0079	−0.2841	0.039*
C6	−0.11979 (14)	0.1907 (3)	−0.15784 (19)	0.0291 (4)
C7	−0.08097 (15)	0.2893 (3)	−0.0520 (2)	0.0345 (5)
H7	−0.1244	0.3647	−0.0124	0.041*
C8	0.02237 (15)	0.2758 (3)	−0.00503 (19)	0.0329 (5)
H8	0.0486	0.3423	0.0659	0.039*
C9	0.55701 (15)	0.1108 (3)	0.2889 (2)	0.0387 (5)
C10	0.63196 (16)	0.1004 (3)	0.4969 (2)	0.0418 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0206 (2)	0.0685 (3)	0.0253 (2)	0.00795 (17)	−0.00440 (13)	−0.01042 (18)
O1	0.0255 (7)	0.0616 (11)	0.0472 (10)	0.0075 (7)	−0.0098 (7)	−0.0105 (8)
N1	0.0220 (8)	0.0336 (9)	0.0266 (8)	0.0001 (7)	−0.0001 (7)	−0.0003 (7)
N2	0.0283 (9)	0.0572 (12)	0.0352 (10)	0.0041 (8)	−0.0043 (8)	−0.0156 (9)
N3	0.0228 (8)	0.0456 (10)	0.0284 (9)	0.0014 (7)	−0.0004 (7)	−0.0017 (8)
N4	0.0268 (9)	0.0838 (15)	0.0301 (10)	0.0107 (9)	−0.0071 (8)	−0.0105 (10)
N5	0.0323 (10)	0.0770 (14)	0.0275 (10)	0.0057 (9)	−0.0024 (8)	−0.0085 (9)
N6	0.0509 (13)	0.0878 (17)	0.0361 (12)	−0.0008 (12)	−0.0124 (10)	−0.0005 (11)
C1	0.0276 (11)	0.0583 (15)	0.0361 (12)	0.0031 (10)	−0.0042 (9)	−0.0135 (11)
C2	0.0223 (10)	0.0478 (12)	0.0282 (10)	0.0037 (9)	−0.0013 (8)	−0.0041 (9)
C3	0.0204 (9)	0.0290 (10)	0.0264 (10)	0.0001 (7)	0.0007 (8)	0.0048 (8)
C4	0.0284 (10)	0.0349 (11)	0.0315 (11)	0.0042 (8)	0.0046 (8)	−0.0036 (9)
C5	0.0319 (11)	0.0371 (11)	0.0269 (10)	−0.0019 (9)	−0.0026 (8)	−0.0033 (9)
C6	0.0219 (9)	0.0359 (11)	0.0287 (10)	0.0001 (8)	−0.0021 (8)	0.0064 (8)
C7	0.0266 (10)	0.0406 (12)	0.0360 (11)	0.0074 (9)	0.0020 (9)	−0.0056 (9)
C8	0.0286 (11)	0.0395 (12)	0.0300 (11)	0.0005 (8)	−0.0004 (9)	−0.0078 (9)
C9	0.0187 (10)	0.0617 (15)	0.0344 (13)	0.0034 (9)	−0.0041 (8)	−0.0028 (11)
C10	0.0328 (11)	0.0620 (15)	0.0304 (12)	−0.0063 (11)	0.0016 (10)	−0.0106 (11)

Geometric parameters (Å, º)

Cu1—N4	1.9797 (19)	N5—C10	1.322 (3)
Cu1—N4^i	1.9797 (19)	N6—C10	1.145 (3)
Cu1—N3^i	1.9964 (16)	C1—H1A	0.9300
Cu1—N3	1.9964 (16)	C2—H2	0.9300
O1—C6	1.365 (2)	C3—C8	1.375 (3)
O1—H1	0.8200	C3—C4	1.377 (3)
N1—C2	1.322 (2)	C4—C5	1.386 (3)
N1—N2	1.368 (2)	C4—H4	0.9300
N1—C3	1.437 (2)	C5—C6	1.377 (3)
N2—C1	1.306 (3)	C5—H5	0.9300
N3—C2	1.332 (2)	C6—C7	1.385 (3)
N3—C1	1.353 (3)	C7—C8	1.383 (3)
N4—C9	1.150 (3)	C7—H7	0.9300
N5—C9	1.294 (3)	C8—H8	0.9300
N4—Cu1—N4^i	180	N3—C2—H2	125.0
N4—Cu1—N3^i	90.43 (7)	C8—C3—C4	120.51 (18)
N4^i—Cu1—N3^i	89.57 (7)	C8—C3—N1	118.93 (17)
N4—Cu1—N3	89.57 (7)	C4—C3—N1	120.55 (17)
N4^i—Cu1—N3	90.43 (7)	C3—C4—C5	119.69 (19)
N3^i—Cu1—N3	180	C3—C4—H4	120.2
C6—O1—H1	109.5	C5—C4—H4	120.2
C2—N1—N2	109.80 (15)	C6—C5—C4	120.13 (19)
C2—N1—C3	129.99 (16)	C6—C5—H5	119.9
N2—N1—C3	120.19 (15)	C4—C5—H5	119.9
C1—N2—N1	102.40 (17)	O1—C6—C5	123.79 (18)
C2—N3—C1	102.70 (16)	O1—C6—C7	116.40 (18)
C2—N3—Cu1	128.70 (14)	C5—C6—C7	119.80 (18)
C1—N3—Cu1	128.58 (14)	C8—C7—C6	120.05 (18)
C9—N4—Cu1	171.15 (18)	C8—C7—H7	120.0
C9—N5—C10	120.4 (2)	C6—C7—H7	120.0
N2—C1—N3	115.04 (19)	C3—C8—C7	119.79 (18)
N2—C1—H1A	122.5	C3—C8—H8	120.1
N3—C1—H1A	122.5	C7—C8—H8	120.1
N1—C2—N3	110.06 (17)	N4—C9—N5	173.4 (2)
N1—C2—H2	125.0	N6—C10—N5	174.6 (3)
C2—N1—N2—C1	−0.1 (2)	N2—N1—C3—C8	13.5 (3)
C3—N1—N2—C1	178.50 (18)	C2—N1—C3—C4	13.4 (3)
N4—Cu1—N3—C2	−172.9 (2)	N2—N1—C3—C4	−164.82 (18)
N4^i—Cu1—N3—C2	7.1 (2)	C8—C3—C4—C5	1.0 (3)
N4—Cu1—N3—C1	5.6 (2)	N1—C3—C4—C5	179.28 (18)
N4^i—Cu1—N3—C1	−174.4 (2)	C3—C4—C5—C6	0.3 (3)
N1—N2—C1—N3	0.3 (3)	C4—C5—C6—O1	177.67 (19)
C2—N3—C1—N2	−0.4 (3)	C4—C5—C6—C7	−1.5 (3)
Cu1—N3—C1—N2	−179.22 (16)	O1—C6—C7—C8	−177.75 (19)
N2—N1—C2—N3	−0.2 (2)	C5—C6—C7—C8	1.5 (3)
C3—N1—C2—N3	−178.57 (18)	C4—C3—C8—C7	−1.0 (3)
C1—N3—C2—N1	0.4 (2)	N1—C3—C8—C7	−179.32 (18)
Cu1—N3—C2—N1	179.15 (13)	C6—C7—C8—C3	−0.2 (3)
C2—N1—C3—C8	−168.3 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2	0.93	2.48	2.804 (3)	101
C1—H1A···N4	0.93	2.53	2.975 (3)	110
O1—H1···N6^ii	0.82	1.95	2.740 (3)	162
C2—H2···N4^i	0.93	2.59	3.001 (3)	107

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