In the title compound, [Cu(C6H4N3)2(H2O)]n, the CuII atom is coordinated by four N atoms from two deprotonated benzotriazole (Bta) ligands and two O atoms from two water molecules. Each deprotonated Bta links two CuII centers via its two neighboring N atoms, giving a chain-like structure. Strong interchain π–π stacking interactions are observed.
Supporting information
CCDC reference: 633972
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (Wave) = 0.000 Å
- R factor = 0.045
- wR factor = 0.104
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C12 H10 Cu1 N6 O1
Atom count from _chemical_formula_moiety:C12 H12 Cu1 N6 O2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
catena-Poly[copper(II)-µ-aqua-di-µ-benzotriazole]
top
Crystal data top
[Cu(C6H4N3)2(H2O)] | F(000) = 1288 |
Mr = 317.80 | Dx = 1.662 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2234 reflections |
a = 26.500 (3) Å | θ = 1.9–25.0° |
b = 6.884 (2) Å | µ = 1.72 mm−1 |
c = 17.124 (3) Å | T = 298 K |
β = 125.609 (3)° | Block, purple |
V = 2539.8 (10) Å3 | 0.40 × 0.30 × 0.28 mm |
Z = 8 | |
Data collection top
Siemens CCD area-detector diffractometer | 2234 independent reflections |
Radiation source: fine-focus sealed tube | 1619 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −31→31 |
Tmin = 0.54, Tmax = 0.62 | k = −8→7 |
6003 measured reflections | l = −20→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0483P)2] where P = (Fo2 + 2Fc2)/3 |
2234 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Special details top
Experimental. Selected FT–IR (KBr, cm-1): 3054 (s), 2395 (s), 1396
(s), 1269 (s), 1219 (m), 1170 (m), 995 (s),
918 (s), 748 (m), 790 (m), 636 (s), 561
(s). |
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 | 0.24280 (2) | 0.28673 (7) | 0.24010 (4) | 0.02364 (19) | |
N1 | 0.20056 (15) | 0.4526 (5) | 0.1228 (2) | 0.0252 (8) | |
N2 | 0.21193 (15) | 0.6457 (5) | 0.1327 (2) | 0.0276 (9) | |
N3 | 0.18701 (16) | 0.7373 (5) | 0.0497 (3) | 0.0329 (9) | |
N4 | 0.33117 (14) | 0.6196 (5) | 0.3079 (2) | 0.0260 (8) | |
N5 | 0.32273 (14) | 0.4290 (5) | 0.2899 (2) | 0.0257 (9) | |
N6 | 0.37320 (15) | 0.3339 (5) | 0.3120 (3) | 0.0296 (9) | |
O1 | 0.22200 (14) | 0.5389 (5) | 0.3214 (2) | 0.0397 (8) | |
H1 | 0.2370 | 0.4781 | 0.3738 | 0.060* | |
H2 | 0.1894 | 0.5973 | 0.3070 | 0.060* | |
C1 | 0.16533 (18) | 0.4168 (6) | 0.0267 (3) | 0.0253 (10) | |
C2 | 0.15674 (19) | 0.5935 (7) | −0.0190 (3) | 0.0277 (10) | |
C3 | 0.1211 (2) | 0.6054 (8) | −0.1199 (3) | 0.0386 (12) | |
H3 | 0.1151 | 0.7228 | −0.1511 | 0.046* | |
C4 | 0.0958 (2) | 0.4371 (8) | −0.1697 (3) | 0.0456 (14) | |
H4 | 0.0714 | 0.4407 | −0.2364 | 0.055* | |
C5 | 0.1055 (2) | 0.2568 (7) | −0.1232 (3) | 0.0387 (12) | |
H5 | 0.0881 | 0.1452 | −0.1602 | 0.046* | |
C6 | 0.1398 (2) | 0.2419 (7) | −0.0250 (3) | 0.0349 (12) | |
H6 | 0.1459 | 0.1237 | 0.0057 | 0.042* | |
C7 | 0.39216 (18) | 0.6551 (6) | 0.3448 (3) | 0.0233 (10) | |
C8 | 0.41780 (18) | 0.4760 (6) | 0.3464 (3) | 0.0259 (10) | |
C9 | 0.48073 (19) | 0.4602 (7) | 0.3808 (3) | 0.0364 (12) | |
H9 | 0.4981 | 0.3419 | 0.3819 | 0.044* | |
C10 | 0.5146 (2) | 0.6271 (8) | 0.4121 (3) | 0.0401 (12) | |
H10 | 0.5562 | 0.6222 | 0.4354 | 0.048* | |
C11 | 0.48867 (19) | 0.8070 (7) | 0.4104 (3) | 0.0378 (12) | |
H11 | 0.5138 | 0.9169 | 0.4326 | 0.045* | |
C12 | 0.42762 (18) | 0.8256 (7) | 0.3771 (3) | 0.0315 (11) | |
H12 | 0.4107 | 0.9448 | 0.3760 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0215 (3) | 0.0133 (3) | 0.0295 (3) | −0.0023 (2) | 0.0111 (2) | 0.0005 (2) |
N1 | 0.0253 (18) | 0.018 (2) | 0.025 (2) | −0.0033 (15) | 0.0106 (17) | −0.0003 (15) |
N2 | 0.0296 (19) | 0.018 (2) | 0.028 (2) | 0.0034 (16) | 0.0127 (18) | 0.0011 (16) |
N3 | 0.041 (2) | 0.021 (2) | 0.032 (2) | −0.0003 (17) | 0.0191 (19) | 0.0010 (16) |
N4 | 0.0230 (18) | 0.015 (2) | 0.033 (2) | −0.0015 (15) | 0.0124 (17) | −0.0015 (16) |
N5 | 0.0224 (19) | 0.017 (2) | 0.032 (2) | −0.0003 (15) | 0.0131 (17) | −0.0007 (15) |
N6 | 0.0246 (19) | 0.019 (2) | 0.039 (2) | 0.0003 (15) | 0.0149 (18) | −0.0011 (16) |
O1 | 0.0462 (19) | 0.028 (2) | 0.056 (2) | 0.0052 (15) | 0.0356 (18) | 0.0064 (15) |
C1 | 0.023 (2) | 0.021 (3) | 0.031 (3) | −0.0024 (18) | 0.015 (2) | −0.0022 (18) |
C2 | 0.032 (2) | 0.019 (3) | 0.034 (3) | 0.0034 (19) | 0.021 (2) | 0.0006 (19) |
C3 | 0.056 (3) | 0.034 (3) | 0.027 (3) | 0.009 (2) | 0.025 (3) | 0.009 (2) |
C4 | 0.047 (3) | 0.058 (4) | 0.026 (3) | 0.001 (3) | 0.018 (3) | −0.007 (2) |
C5 | 0.047 (3) | 0.031 (3) | 0.032 (3) | −0.013 (2) | 0.019 (2) | −0.012 (2) |
C6 | 0.041 (3) | 0.017 (3) | 0.041 (3) | −0.005 (2) | 0.021 (2) | −0.005 (2) |
C7 | 0.024 (2) | 0.017 (3) | 0.022 (2) | −0.0013 (17) | 0.0092 (19) | −0.0003 (16) |
C8 | 0.023 (2) | 0.021 (3) | 0.031 (3) | −0.0001 (18) | 0.014 (2) | −0.0003 (18) |
C9 | 0.025 (2) | 0.036 (3) | 0.044 (3) | 0.004 (2) | 0.018 (2) | 0.001 (2) |
C10 | 0.025 (2) | 0.036 (3) | 0.053 (3) | −0.001 (2) | 0.020 (2) | 0.002 (2) |
C11 | 0.029 (2) | 0.030 (3) | 0.042 (3) | −0.009 (2) | 0.014 (2) | −0.002 (2) |
C12 | 0.030 (2) | 0.019 (3) | 0.038 (3) | −0.0040 (18) | 0.016 (2) | −0.0017 (19) |
Geometric parameters (Å, º) top
Cu1—N4i | 1.991 (3) | C2—C3 | 1.409 (6) |
Cu1—N1 | 1.994 (3) | C3—C4 | 1.361 (7) |
Cu1—N5 | 2.017 (3) | C3—H3 | 0.9300 |
Cu1—N2i | 2.021 (3) | C4—C5 | 1.415 (7) |
N1—N2 | 1.352 (5) | C4—H4 | 0.9300 |
N1—C1 | 1.360 (5) | C5—C6 | 1.373 (6) |
N2—N3 | 1.326 (5) | C5—H5 | 0.9300 |
N2—Cu1ii | 2.021 (3) | C6—H6 | 0.9300 |
N3—C2 | 1.382 (6) | C7—C8 | 1.400 (6) |
N4—N5 | 1.337 (5) | C7—C12 | 1.400 (6) |
N4—C7 | 1.372 (5) | C8—C9 | 1.413 (6) |
N4—Cu1ii | 1.991 (3) | C9—C10 | 1.361 (7) |
N5—N6 | 1.331 (4) | C9—H9 | 0.9300 |
N6—C8 | 1.375 (5) | C10—C11 | 1.408 (7) |
O1—H1 | 0.8499 | C10—H10 | 0.9300 |
O1—H2 | 0.8500 | C11—C12 | 1.373 (6) |
C1—C2 | 1.391 (6) | C11—H11 | 0.9300 |
C1—C6 | 1.412 (6) | C12—H12 | 0.9300 |
| | | |
N4i—Cu1—N1 | 94.28 (14) | N3—C2—C1 | 108.9 (4) |
N4i—Cu1—N5 | 173.68 (15) | N3—C2—C3 | 130.2 (4) |
N1—Cu1—N5 | 89.03 (14) | C1—C2—C3 | 120.9 (4) |
N4i—Cu1—N2i | 89.50 (14) | C4—C3—C2 | 116.9 (5) |
N1—Cu1—N2i | 173.77 (15) | C4—C3—H3 | 121.5 |
N5—Cu1—N2i | 87.69 (14) | C2—C3—H3 | 121.5 |
N4i—Cu1—Cu1ii | 129.90 (10) | C3—C4—C5 | 122.2 (5) |
N1—Cu1—Cu1ii | 59.60 (10) | C3—C4—H4 | 118.9 |
N5—Cu1—Cu1ii | 56.40 (10) | C5—C4—H4 | 118.9 |
N2i—Cu1—Cu1ii | 114.22 (11) | C6—C5—C4 | 121.9 (4) |
N2—N1—C1 | 106.0 (3) | C6—C5—H5 | 119.0 |
N2—N1—Cu1 | 118.9 (3) | C4—C5—H5 | 119.0 |
C1—N1—Cu1 | 134.6 (3) | C5—C6—C1 | 116.0 (4) |
N3—N2—N1 | 113.4 (3) | C5—C6—H6 | 122.0 |
N3—N2—Cu1ii | 122.6 (3) | C1—C6—H6 | 122.0 |
N1—N2—Cu1ii | 123.9 (3) | N4—C7—C8 | 106.3 (4) |
N2—N3—C2 | 104.6 (4) | N4—C7—C12 | 132.1 (4) |
N5—N4—C7 | 105.9 (3) | C8—C7—C12 | 121.6 (4) |
N5—N4—Cu1ii | 118.7 (2) | N6—C8—C7 | 109.4 (4) |
C7—N4—Cu1ii | 134.4 (3) | N6—C8—C9 | 129.4 (4) |
N6—N5—N4 | 114.3 (3) | C7—C8—C9 | 121.2 (4) |
N6—N5—Cu1 | 121.0 (3) | C10—C9—C8 | 116.5 (5) |
N4—N5—Cu1 | 124.6 (2) | C10—C9—H9 | 121.7 |
N5—N6—C8 | 104.0 (3) | C8—C9—H9 | 121.7 |
N3i—O1—N6ii | 178.15 (16) | C9—C10—C11 | 122.1 (4) |
N3i—O1—H1 | 36.1 | C9—C10—H10 | 118.9 |
N6ii—O1—H1 | 143.8 | C11—C10—H10 | 118.9 |
N3i—O1—H2 | 142.7 | C12—C11—C10 | 122.2 (4) |
N6ii—O1—H2 | 36.5 | C12—C11—H11 | 118.9 |
H1—O1—H2 | 108.1 | C10—C11—H11 | 118.9 |
N1—C1—C2 | 107.1 (4) | C11—C12—C7 | 116.3 (4) |
N1—C1—C6 | 130.8 (4) | C11—C12—H12 | 121.8 |
C2—C1—C6 | 122.1 (4) | C7—C12—H12 | 121.8 |
| | | |
N4i—Cu1—N1—N2 | 140.9 (3) | C6—C1—C2—N3 | −179.9 (4) |
N5—Cu1—N1—N2 | −44.5 (3) | N1—C1—C2—C3 | −179.1 (4) |
N4i—Cu1—N1—C1 | −48.1 (4) | C6—C1—C2—C3 | 0.9 (6) |
N5—Cu1—N1—C1 | 126.5 (4) | N3—C2—C3—C4 | −179.0 (4) |
C1—N1—N2—N3 | −0.6 (4) | C1—C2—C3—C4 | 0.0 (6) |
Cu1—N1—N2—N3 | 172.7 (3) | C2—C3—C4—C5 | −1.2 (7) |
C1—N1—N2—Cu1ii | 175.3 (3) | C3—C4—C5—C6 | 1.6 (8) |
Cu1—N1—N2—Cu1ii | −11.3 (4) | C4—C5—C6—C1 | −0.6 (7) |
N1—N2—N3—C2 | 0.6 (5) | N1—C1—C6—C5 | 179.4 (4) |
Cu1ii—N2—N3—C2 | −175.4 (3) | C2—C1—C6—C5 | −0.6 (6) |
C7—N4—N5—N6 | 0.2 (4) | N5—N4—C7—C8 | 0.3 (4) |
Cu1ii—N4—N5—N6 | 170.6 (3) | Cu1ii—N4—C7—C8 | −167.9 (3) |
C7—N4—N5—Cu1 | 177.0 (3) | N5—N4—C7—C12 | −179.7 (4) |
Cu1ii—N4—N5—Cu1 | −12.6 (4) | Cu1ii—N4—C7—C12 | 12.1 (7) |
N1—Cu1—N5—N6 | −122.4 (3) | N5—N6—C8—C7 | 0.7 (4) |
N2i—Cu1—N5—N6 | 62.9 (3) | N5—N6—C8—C9 | 180.0 (4) |
N1—Cu1—N5—N4 | 61.0 (3) | N4—C7—C8—N6 | −0.6 (5) |
N2i—Cu1—N5—N4 | −113.7 (3) | C12—C7—C8—N6 | 179.4 (4) |
N4—N5—N6—C8 | −0.5 (4) | N4—C7—C8—C9 | −180.0 (4) |
Cu1—N5—N6—C8 | −177.5 (3) | C12—C7—C8—C9 | 0.0 (6) |
N2—N1—C1—C2 | 0.3 (4) | N6—C8—C9—C10 | −179.1 (4) |
Cu1—N1—C1—C2 | −171.5 (3) | C7—C8—C9—C10 | 0.2 (7) |
N2—N1—C1—C6 | −179.8 (4) | C8—C9—C10—C11 | −0.2 (7) |
Cu1—N1—C1—C6 | 8.5 (7) | C9—C10—C11—C12 | 0.0 (8) |
N2—N3—C2—C1 | −0.4 (5) | C10—C11—C12—C7 | 0.1 (7) |
N2—N3—C2—C3 | 178.7 (4) | N4—C7—C12—C11 | 179.8 (4) |
N1—C1—C2—N3 | 0.1 (5) | C8—C7—C12—C11 | −0.1 (6) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N3i | 0.85 | 2.33 | 2.966 (5) | 132 |
O1—H2···N6ii | 0.85 | 2.37 | 2.999 (5) | 131 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2. |