Buy article online - an online subscription or single-article purchase is required to access this article.
In the title centrosymmetric complex, [Cu(C
2N
3)
2(C
8H
7N
3O)
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.
Supporting information
CCDC reference: 633915
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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 = 517.98 | 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) Å3 | 0.24 × 0.23 × 0.22 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H-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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cu1—N4 | 1.9797 (19) | N5—C10 | 1.322 (3) |
Cu1—N4i | 1.9797 (19) | N6—C10 | 1.145 (3) |
Cu1—N3i | 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—N4i | 180 | N3—C2—H2 | 125.0 |
N4—Cu1—N3i | 90.43 (7) | C8—C3—C4 | 120.51 (18) |
N4i—Cu1—N3i | 89.57 (7) | C8—C3—N1 | 118.93 (17) |
N4—Cu1—N3 | 89.57 (7) | C4—C3—N1 | 120.55 (17) |
N4i—Cu1—N3 | 90.43 (7) | C3—C4—C5 | 119.69 (19) |
N3i—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) |
N4i—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) |
N4i—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) top
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···N6ii | 0.82 | 1.95 | 2.740 (3) | 162 |
C2—H2···N4i | 0.93 | 2.59 | 3.001 (3) | 107 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y, z−1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.