A unique and stable silver benzotriazole complex, [Ag2(NO3)2(C6H3N3)(H2O)]n, is reported in which the benzotriazole is coordinated to the silver as a neutral donor ligand, bridging two silver atoms. Weakly bound nitrate anions and H2O complete the coordination environment. The structure is built upon a chain of alternating units [–Ag-HBZT-Ag-(NO3)2-H2O–] where the three available bonding sites of the HBZT (1H-1,2,3-benzotriazole) ligand are fully occupied: two N atoms of the azine component are bound to silver and the third retains the original hydrogen.
Supporting information
CCDC reference: 620709
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.012 Å
- R factor = 0.037
- wR factor = 0.078
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.796 0.974
Tmin and Tmax expected: 0.515 0.934
RR = 1.481
Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.50
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.46
From the CIF: _reflns_number_total 2264
Count of symmetry unique reflns 1375
Completeness (_total/calc) 164.65%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 889
Fraction of Friedel pairs measured 0.647
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and MaterialsStudio (Accelrys Inc., 2002); software used to prepare material for publication: SHELXTL and MaterialsStudio.
Poly[aqua-µ-1
H-1,2,3-benzotriazole-µ-nitrato-nitratodisilver(I)]
top
Crystal data top
[Ag2(NO3)2(C6H3N3)(H2O)] | F(000) = 904 |
Mr = 474.89 | Dx = 2.728 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 5272 reflections |
a = 7.0503 (3) Å | θ = 1.0–27.5° |
b = 10.9102 (5) Å | µ = 3.43 mm−1 |
c = 15.0341 (6) Å | T = 294 K |
V = 1156.43 (9) Å3 | Rod, white |
Z = 4 | 0.20 × 0.20 × 0.02 mm |
Data collection top
Nonius KappaCCD diffractometer | 2264 independent reflections |
Radiation source: fine-focus sealed tube | 1546 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 4.5° |
CCD scans | h = −7→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −12→14 |
Tmin = 0.796, Tmax = 0.974 | l = −15→19 |
8772 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0331P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
2264 reflections | Δρmax = 0.61 e Å−3 |
181 parameters | Δρmin = −0.78 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (5) |
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 | |
Ag1 | 0.65513 (8) | 0.66622 (6) | 0.53586 (4) | 0.04770 (19) | |
Ag2 | 0.95983 (9) | 1.01065 (6) | 0.71697 (6) | 0.0565 (2) | |
N1 | 0.5737 (8) | 0.3924 (7) | 0.5988 (4) | 0.0312 (16) | |
N2 | 0.6346 (8) | 0.4607 (5) | 0.5334 (5) | 0.0338 (13) | |
N3 | 0.6890 (8) | 0.3859 (6) | 0.4668 (4) | 0.0296 (15) | |
H3 | 0.7328 | 0.4107 | 0.4165 | 0.035* | |
N4 | 0.4117 (10) | 0.7011 (8) | 0.3688 (5) | 0.0402 (19) | |
N5 | 0.8769 (8) | 0.7329 (7) | 0.7079 (5) | 0.0336 (15) | |
O7 | 0.6637 (7) | 0.9934 (5) | 0.8128 (4) | 0.0385 (13) | |
O1 | 0.4419 (8) | 0.7701 (6) | 0.4357 (4) | 0.0540 (17) | |
O2 | 0.4781 (8) | 0.5969 (6) | 0.3682 (4) | 0.0459 (16) | |
O3 | 0.3164 (10) | 0.7397 (7) | 0.3059 (4) | 0.0653 (19) | |
O4 | 0.8194 (7) | 0.7907 (6) | 0.6390 (4) | 0.0471 (16) | |
O5 | 0.8513 (7) | 0.6208 (5) | 0.7142 (4) | 0.0438 (13) | |
O6 | 0.9612 (8) | 0.7931 (6) | 0.7661 (4) | 0.0468 (15) | |
C1 | 0.5906 (10) | 0.2720 (8) | 0.5754 (6) | 0.0263 (18) | |
C2 | 0.5482 (10) | 0.1638 (8) | 0.6213 (5) | 0.0326 (19) | |
H2 | 0.4959 | 0.1653 | 0.6781 | 0.039* | |
C3 | 0.5873 (11) | 0.0553 (8) | 0.5787 (6) | 0.039 (2) | |
H3A | 0.5623 | −0.0182 | 0.6079 | 0.047* | |
C4 | 0.6638 (10) | 0.0520 (9) | 0.4926 (6) | 0.037 (2) | |
H4 | 0.6868 | −0.0236 | 0.4662 | 0.045* | |
C5 | 0.7060 (10) | 0.1574 (8) | 0.4460 (5) | 0.0334 (19) | |
H5A | 0.7581 | 0.1549 | 0.3892 | 0.040* | |
C6 | 0.6660 (10) | 0.2682 (8) | 0.4890 (5) | 0.0281 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0586 (4) | 0.0413 (4) | 0.0433 (3) | −0.0064 (3) | 0.0005 (4) | −0.0007 (4) |
Ag2 | 0.0822 (5) | 0.0516 (5) | 0.0356 (3) | −0.0179 (4) | 0.0150 (4) | 0.0025 (4) |
N1 | 0.031 (3) | 0.037 (5) | 0.026 (4) | −0.001 (3) | 0.001 (3) | 0.002 (3) |
N2 | 0.029 (3) | 0.042 (4) | 0.031 (3) | 0.002 (3) | 0.001 (3) | 0.002 (4) |
N3 | 0.032 (3) | 0.036 (4) | 0.021 (3) | 0.001 (3) | 0.002 (3) | 0.002 (3) |
N4 | 0.042 (4) | 0.041 (6) | 0.038 (4) | 0.004 (4) | 0.007 (3) | 0.007 (4) |
N5 | 0.036 (3) | 0.033 (5) | 0.031 (4) | 0.007 (3) | 0.001 (3) | 0.003 (4) |
O7 | 0.044 (3) | 0.038 (4) | 0.033 (3) | 0.000 (2) | −0.008 (2) | 0.006 (3) |
O1 | 0.057 (4) | 0.054 (5) | 0.052 (4) | 0.007 (3) | 0.001 (3) | −0.019 (3) |
O2 | 0.063 (4) | 0.035 (4) | 0.040 (4) | 0.012 (3) | 0.003 (3) | −0.003 (3) |
O3 | 0.079 (4) | 0.078 (6) | 0.038 (3) | 0.038 (4) | −0.005 (3) | 0.007 (4) |
O4 | 0.054 (4) | 0.049 (4) | 0.038 (3) | −0.003 (3) | −0.010 (3) | 0.004 (3) |
O5 | 0.051 (3) | 0.032 (4) | 0.049 (3) | 0.007 (2) | −0.006 (4) | −0.001 (3) |
O6 | 0.047 (3) | 0.054 (4) | 0.039 (3) | −0.005 (3) | −0.008 (3) | −0.003 (3) |
C1 | 0.020 (4) | 0.035 (6) | 0.024 (4) | −0.002 (3) | 0.000 (3) | 0.003 (4) |
C2 | 0.027 (4) | 0.038 (6) | 0.033 (4) | −0.008 (4) | −0.001 (3) | 0.015 (4) |
C3 | 0.037 (5) | 0.032 (6) | 0.047 (5) | −0.001 (4) | −0.002 (4) | 0.006 (5) |
C4 | 0.030 (5) | 0.044 (6) | 0.038 (5) | 0.004 (4) | −0.002 (4) | −0.005 (4) |
C5 | 0.030 (4) | 0.047 (6) | 0.023 (4) | −0.002 (4) | −0.001 (3) | 0.004 (4) |
C6 | 0.026 (4) | 0.031 (5) | 0.027 (4) | 0.004 (4) | 0.000 (3) | −0.001 (4) |
Geometric parameters (Å, º) top
Ag1—N2 | 2.247 (6) | N4—O1 | 1.274 (9) |
Ag1—O4 | 2.365 (6) | N5—O5 | 1.239 (8) |
Ag1—O1 | 2.411 (6) | N5—O6 | 1.246 (9) |
Ag2—N1i | 2.218 (7) | N5—O4 | 1.278 (8) |
Ag2—O6 | 2.486 (7) | O2—Ag2iv | 2.500 (6) |
Ag2—O2ii | 2.500 (6) | C1—C2 | 1.400 (11) |
Ag2—O7 | 2.544 (5) | C1—C6 | 1.404 (9) |
N1—N2 | 1.307 (9) | C2—C3 | 1.374 (12) |
N1—C1 | 1.365 (10) | C2—H2 | 0.9300 |
N1—Ag2iii | 2.218 (6) | C3—C4 | 1.403 (10) |
N2—N3 | 1.348 (9) | C3—H3A | 0.9300 |
N3—C6 | 1.337 (11) | C4—C5 | 1.379 (11) |
N3—H3 | 0.8600 | C4—H4 | 0.9300 |
N4—O2 | 1.229 (9) | C5—C6 | 1.399 (11) |
N4—O3 | 1.235 (9) | C5—H5A | 0.9300 |
| | | |
N2—Ag1—O4 | 128.0 (2) | O6—N5—O4 | 117.4 (7) |
N2—Ag1—O1 | 114.8 (2) | N4—O1—Ag1 | 108.6 (5) |
O4—Ag1—O1 | 116.4 (2) | N4—O2—Ag2iv | 114.9 (5) |
N1i—Ag2—O6 | 133.8 (2) | N5—O4—Ag1 | 113.8 (5) |
N1i—Ag2—O2ii | 119.0 (2) | N5—O6—Ag2 | 107.0 (5) |
O6—Ag2—O2ii | 95.1 (2) | N1—C1—C2 | 131.7 (7) |
N1i—Ag2—O7 | 141.8 (2) | N1—C1—C6 | 107.5 (8) |
O6—Ag2—O7 | 76.35 (19) | C2—C1—C6 | 120.8 (9) |
O2ii—Ag2—O7 | 69.89 (18) | C3—C2—C1 | 117.0 (8) |
N2—N1—C1 | 109.0 (6) | C3—C2—H2 | 121.5 |
N2—N1—Ag2iii | 116.7 (5) | C1—C2—H2 | 121.5 |
C1—N1—Ag2iii | 134.2 (5) | C2—C3—C4 | 121.9 (9) |
N1—N2—N3 | 107.9 (6) | C2—C3—H3A | 119.0 |
N1—N2—Ag1 | 125.3 (6) | C4—C3—H3A | 119.0 |
N3—N2—Ag1 | 126.7 (5) | C5—C4—C3 | 122.1 (9) |
C6—N3—N2 | 111.2 (6) | C5—C4—H4 | 119.0 |
C6—N3—H3 | 124.4 | C3—C4—H4 | 119.0 |
N2—N3—H3 | 124.4 | C4—C5—C6 | 116.2 (7) |
O2—N4—O3 | 121.1 (8) | C4—C5—H5A | 121.9 |
O2—N4—O1 | 119.2 (7) | C6—C5—H5A | 121.9 |
O3—N4—O1 | 119.6 (8) | N3—C6—C5 | 133.6 (7) |
O5—N5—O6 | 122.4 (7) | N3—C6—C1 | 104.4 (7) |
O5—N5—O4 | 120.2 (7) | C5—C6—C1 | 122.0 (9) |
| | | |
C1—N1—N2—N3 | 0.8 (8) | O4—N5—O6—Ag2 | 2.7 (7) |
Ag2iii—N1—N2—N3 | −177.0 (4) | N1i—Ag2—O6—N5 | −60.4 (6) |
C1—N1—N2—Ag1 | −176.8 (4) | O2ii—Ag2—O6—N5 | 160.1 (5) |
Ag2iii—N1—N2—Ag1 | 5.3 (7) | O7—Ag2—O6—N5 | 92.3 (5) |
O4—Ag1—N2—N1 | 55.9 (6) | N2—N1—C1—C2 | 179.1 (7) |
O1—Ag1—N2—N1 | −113.1 (6) | Ag2iii—N1—C1—C2 | −3.6 (12) |
O4—Ag1—N2—N3 | −121.3 (5) | N2—N1—C1—C6 | −0.5 (8) |
O1—Ag1—N2—N3 | 69.7 (5) | Ag2iii—N1—C1—C6 | 176.8 (5) |
N1—N2—N3—C6 | −0.8 (8) | N1—C1—C2—C3 | −178.3 (7) |
Ag1—N2—N3—C6 | 176.7 (5) | C6—C1—C2—C3 | 1.3 (10) |
O2—N4—O1—Ag1 | 5.1 (9) | C1—C2—C3—C4 | −0.9 (11) |
O3—N4—O1—Ag1 | −175.0 (6) | C2—C3—C4—C5 | 0.6 (11) |
N2—Ag1—O1—N4 | −29.8 (6) | C3—C4—C5—C6 | −0.8 (10) |
O4—Ag1—O1—N4 | 159.9 (5) | N2—N3—C6—C5 | −177.4 (8) |
O3—N4—O2—Ag2iv | 27.0 (9) | N2—N3—C6—C1 | 0.5 (7) |
O1—N4—O2—Ag2iv | −153.1 (5) | C4—C5—C6—N3 | 178.8 (7) |
O5—N5—O4—Ag1 | 2.8 (8) | C4—C5—C6—C1 | 1.2 (10) |
O6—N5—O4—Ag1 | −178.5 (5) | N1—C1—C6—N3 | 0.0 (7) |
N2—Ag1—O4—N5 | −11.5 (6) | C2—C1—C6—N3 | −179.7 (7) |
O1—Ag1—O4—N5 | 157.3 (4) | N1—C1—C6—C5 | 178.2 (7) |
O5—N5—O6—Ag2 | −178.7 (5) | C2—C1—C6—C5 | −1.5 (10) |
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) −x+3/2, y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z; (iv) −x+3/2, y−1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O7iv | 0.86 | 1.94 | 2.795 (8) | 170 |
Symmetry code: (iv) −x+3/2, y−1/2, z−1/2. |