The title compound, [Ag(NO
2)(C
6H
12N
2)(H
2O)]
n, is a polymeric 1,4-diazabicyclo[2,2,2]octane–Ag
I complex. Each Ag atom is five-coordinated by two N atoms from two different 1,4-diazabicyclo[2,2,2]octane ligands, two O atoms of one nitrite anion and another O atom of a coordinated water molecule, forming a severely distorted square-pyramidal coordination environment. In the crystal structure, molecules are connected by intermolecular O—H
O hydrogen bonds, forming a three-dimensional network.
Supporting information
CCDC reference: 258627
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.011 Å
- R factor = 0.040
- wR factor = 0.096
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O2
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N2
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
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 25.03
From the CIF: _reflns_number_total 1478
Count of symmetry unique reflns 888
Completeness (_total/calc) 166.44%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 590
Fraction of Friedel pairs measured 0.664
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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
catena-Poly[[aquanitritosilver(I)]µ-1,4-diazabicyclo[2,2,2]octane-
κ2N:
N']
top
Crystal data top
[Ag(NO2)(C6H12N2)(H2O)] | Dx = 1.922 Mg m−3 |
Mr = 284.07 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 4594 reflections |
Hall symbol: P 4cw | θ = 3.6–26.5° |
a = 6.706 (3) Å | µ = 2.03 mm−1 |
c = 21.834 (16) Å | T = 298 K |
V = 981.9 (10) Å3 | Block, colourless |
Z = 4 | 0.48 × 0.43 × 0.37 mm |
F(000) = 568 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1478 independent reflections |
Radiation source: fine-focus sealed tube | 1448 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.402, Tmax = 0.473 | k = −7→7 |
5148 measured reflections | l = −25→18 |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.29 | (Δ/σ)max < 0.001 |
1478 reflections | Δρmax = 0.52 e Å−3 |
124 parameters | Δρmin = −1.58 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 590 Friedels |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.07 (7) |
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 | 0.16956 (6) | 0.52184 (6) | 0.23199 (5) | 0.03857 (19) | |
O1 | 0.4885 (7) | 0.3271 (7) | 0.2252 (3) | 0.0572 (13) | |
O2 | 0.3196 (9) | 0.2432 (9) | 0.3006 (3) | 0.0668 (16) | |
O3 | −0.1153 (8) | 0.3321 (10) | 0.1774 (3) | 0.0612 (15) | |
N1 | 0.2596 (7) | 0.7341 (7) | 0.1508 (2) | 0.0292 (10) | |
N2 | 0.3631 (8) | 0.9721 (6) | 0.0633 (3) | 0.0288 (11) | |
N3 | 0.4778 (9) | 0.2228 (10) | 0.2716 (4) | 0.0499 (15) | |
C1 | 0.4736 (10) | 0.7860 (11) | 0.1562 (4) | 0.0435 (15) | |
H1A | 0.5526 | 0.6650 | 0.1582 | 0.052* | |
H1B | 0.4956 | 0.8607 | 0.1936 | 0.052* | |
C2 | 0.5407 (9) | 0.9129 (11) | 0.1002 (4) | 0.0436 (15) | |
H2A | 0.6101 | 1.0312 | 0.1143 | 0.052* | |
H2B | 0.6317 | 0.8361 | 0.0750 | 0.052* | |
C3 | 0.1411 (12) | 0.9238 (11) | 0.1532 (4) | 0.0506 (18) | |
H3A | 0.1541 | 0.9841 | 0.1934 | 0.061* | |
H3B | 0.0012 | 0.8949 | 0.1462 | 0.061* | |
C4 | 0.2177 (12) | 1.0699 (10) | 0.1037 (4) | 0.0463 (16) | |
H4A | 0.1060 | 1.1177 | 0.0796 | 0.056* | |
H4B | 0.2796 | 1.1840 | 0.1233 | 0.056* | |
C5 | 0.2290 (12) | 0.6403 (10) | 0.0900 (3) | 0.0475 (17) | |
H5A | 0.0928 | 0.5928 | 0.0869 | 0.057* | |
H5B | 0.3173 | 0.5265 | 0.0859 | 0.057* | |
C6 | 0.2703 (11) | 0.7887 (10) | 0.0382 (3) | 0.0443 (15) | |
H6A | 0.3589 | 0.7284 | 0.0084 | 0.053* | |
H6B | 0.1464 | 0.8224 | 0.0178 | 0.053* | |
H1 | −0.147 (14) | 0.333 (18) | 0.1402 (12) | 0.080* | |
H2 | −0.215 (9) | 0.300 (16) | 0.198 (4) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0407 (3) | 0.0465 (3) | 0.0285 (3) | 0.00881 (16) | 0.01154 (18) | 0.0105 (2) |
O1 | 0.054 (2) | 0.061 (3) | 0.057 (4) | 0.005 (2) | 0.015 (3) | 0.015 (3) |
O2 | 0.068 (3) | 0.072 (3) | 0.060 (4) | 0.019 (3) | 0.023 (3) | 0.017 (3) |
O3 | 0.044 (3) | 0.095 (4) | 0.045 (3) | −0.011 (3) | 0.004 (2) | −0.016 (3) |
N1 | 0.036 (2) | 0.029 (2) | 0.022 (3) | 0.0027 (16) | 0.0007 (18) | 0.0039 (19) |
N2 | 0.039 (2) | 0.026 (2) | 0.021 (3) | −0.0013 (16) | 0.000 (2) | 0.0052 (17) |
N3 | 0.052 (3) | 0.046 (3) | 0.052 (5) | 0.012 (2) | −0.007 (3) | 0.009 (3) |
C1 | 0.042 (3) | 0.048 (3) | 0.040 (4) | −0.005 (3) | −0.008 (3) | 0.018 (3) |
C2 | 0.044 (4) | 0.047 (4) | 0.040 (4) | −0.007 (3) | −0.008 (3) | 0.013 (3) |
C3 | 0.061 (4) | 0.048 (4) | 0.043 (5) | 0.015 (3) | 0.012 (3) | 0.014 (3) |
C4 | 0.062 (4) | 0.039 (3) | 0.037 (4) | 0.013 (3) | 0.016 (3) | 0.010 (3) |
C5 | 0.069 (4) | 0.037 (3) | 0.037 (4) | −0.017 (3) | 0.001 (3) | −0.001 (3) |
C6 | 0.059 (4) | 0.041 (3) | 0.033 (4) | −0.014 (3) | −0.005 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
Ag1—N2i | 2.345 (5) | C1—C2 | 1.556 (10) |
Ag1—N1 | 2.353 (5) | C1—H1A | 0.9700 |
Ag1—O1 | 2.511 (5) | C1—H1B | 0.9700 |
Ag1—O3 | 2.586 (5) | C2—H2A | 0.9700 |
Ag1—O2 | 2.598 (6) | C2—H2B | 0.9700 |
O1—N3 | 1.235 (10) | C3—C4 | 1.547 (10) |
O2—N3 | 1.243 (9) | C3—H3A | 0.9700 |
O3—H1 | 0.84 (3) | C3—H3B | 0.9700 |
O3—H2 | 0.83 (7) | C4—H4A | 0.9700 |
N1—C1 | 1.481 (8) | C4—H4B | 0.9700 |
N1—C5 | 1.482 (9) | C5—C6 | 1.532 (9) |
N1—C3 | 1.501 (8) | C5—H5A | 0.9700 |
N2—C4 | 1.470 (8) | C5—H5B | 0.9700 |
N2—C6 | 1.483 (8) | C6—H6A | 0.9700 |
N2—C2 | 1.491 (8) | C6—H6B | 0.9700 |
N2—Ag1ii | 2.345 (5) | | |
| | | |
N2i—Ag1—N1 | 121.09 (17) | C2—C1—H1B | 109.6 |
N2i—Ag1—O1 | 134.2 (2) | H1A—C1—H1B | 108.1 |
N1—Ag1—O1 | 92.92 (17) | N2—C2—C1 | 109.8 (5) |
N2i—Ag1—O3 | 95.37 (18) | N2—C2—H2A | 109.7 |
N1—Ag1—O3 | 98.0 (2) | C1—C2—H2A | 109.7 |
O1—Ag1—O3 | 110.2 (2) | N2—C2—H2B | 109.7 |
N2i—Ag1—O2 | 91.09 (19) | C1—C2—H2B | 109.7 |
N1—Ag1—O2 | 140.39 (17) | H2A—C2—H2B | 108.2 |
O1—Ag1—O2 | 47.95 (19) | N1—C3—C4 | 109.6 (6) |
O3—Ag1—O2 | 101.4 (2) | N1—C3—H3A | 109.7 |
N3—O1—Ag1 | 101.3 (4) | C4—C3—H3A | 109.7 |
N3—O2—Ag1 | 96.7 (5) | N1—C3—H3B | 109.7 |
Ag1—O3—H1 | 129 (7) | C4—C3—H3B | 109.7 |
Ag1—O3—H2 | 118 (7) | H3A—C3—H3B | 108.2 |
H1—O3—H2 | 109 (8) | N2—C4—C3 | 110.9 (5) |
C1—N1—C5 | 107.8 (5) | N2—C4—H4A | 109.5 |
C1—N1—C3 | 108.1 (5) | C3—C4—H4A | 109.5 |
C5—N1—C3 | 108.5 (6) | N2—C4—H4B | 109.5 |
C1—N1—Ag1 | 109.3 (4) | C3—C4—H4B | 109.5 |
C5—N1—Ag1 | 112.5 (4) | H4A—C4—H4B | 108.0 |
C3—N1—Ag1 | 110.5 (4) | N1—C5—C6 | 111.1 (5) |
C4—N2—C6 | 108.2 (5) | N1—C5—H5A | 109.4 |
C4—N2—C2 | 108.9 (6) | C6—C5—H5A | 109.4 |
C6—N2—C2 | 108.3 (5) | N1—C5—H5B | 109.4 |
C4—N2—Ag1ii | 114.9 (4) | C6—C5—H5B | 109.4 |
C6—N2—Ag1ii | 109.1 (4) | H5A—C5—H5B | 108.0 |
C2—N2—Ag1ii | 107.3 (4) | N2—C6—C5 | 110.0 (6) |
O1—N3—O2 | 113.9 (5) | N2—C6—H6A | 109.7 |
N1—C1—C2 | 110.2 (5) | C5—C6—H6A | 109.7 |
N1—C1—H1A | 109.6 | N2—C6—H6B | 109.7 |
C2—C1—H1A | 109.6 | C5—C6—H6B | 109.7 |
N1—C1—H1B | 109.6 | H6A—C6—H6B | 108.2 |
Symmetry codes: (i) y−1, −x+1, z+1/4; (ii) −y+1, x+1, z−1/4. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1···O2iii | 0.84 (3) | 2.06 (4) | 2.899 (9) | 176 (9) |
O3—H2···O1iv | 0.83 (7) | 2.08 (5) | 2.854 (7) | 154 (10) |
Symmetry codes: (iii) −y, x, z−1/4; (iv) x−1, y, z. |