metal-organic compounds
Bis[μ-(E)-N-(pyridin-3-ylmethylidene)hydroxyamine]-κ2N1:N3;κ2N3:N1-bis{[(E)-N-(pyridin-3-ylmethylidene-κN)hydroxyamine]silver(I)} dinitrate
aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my
In the centrosymmetric dinuclear title AgI compound, [Ag2(C6H6N2O)4](NO3)2, the aromatic amine-coordinated AgI atom is further bridged by two hydroxylamine molecules that use aromatic and oxime N atoms for bridging, and it exists in a distorted trigonal-planar geometry. In the crystal, the nitrate anions link to the dinuclear compound molecules via O—H⋯O hydrogen bonds, generating a chain running along the a-axis direction.
Related literature
For bis(nicotinylaldehyde oxime)silver perchlorate, see: Xu et al. (2012) and for (nitrato)(picolinaldehyde oxime)silver, see: Abu-Youssef et al. (2010).
Experimental
Crystal data
|
Refinement
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812045898/xu5646sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045898/xu5646Isup2.hkl
Nicotinyladehyde oxime was synthesized from the reaction of nicotinylaldehyde and hydroxylamine. Silver nitrate (1 mmol) dissolved in water (5 ml) was added to nicotinylaldehyde oxime (1 mmol) dissolved in ethanol (5 ml). The solution was filtered and set aside, away from light, for the growth of colorless crystals.
Carbon- and oxygen-bound H-atoms were placed in calculated positions (C–H 0.93 Å, O–H 0.84 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2–1.5U(C,O).The (-1 3 3), (5 - 10 1), (6 - 9 5) and (0 9 1) reflections were omitted.
The final difference Fourier map had a peak at 0.88 Å from Ag1.
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Ag(C6H6N2O)2]2 2NO3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
[Ag2(C6H6N2O)4](NO3)2 | Z = 1 |
Mr = 828.27 | F(000) = 412 |
Triclinic, P1 | Dx = 1.863 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2913 (10) Å | Cell parameters from 6130 reflections |
b = 8.3395 (10) Å | θ = 3.0–27.4° |
c = 13.1415 (17) Å | µ = 1.40 mm−1 |
α = 92.934 (4)° | T = 293 K |
β = 95.008 (4)° | Prism, colorless |
γ = 111.360 (3)° | 0.24 × 0.21 × 0.17 mm |
V = 738.38 (16) Å3 |
Rigaku R-AXIS RAPID IP diffractometer | 3341 independent reflections |
Radiation source: fine-focus sealed tube | 2896 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scan | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.730, Tmax = 0.797 | k = −10→10 |
7293 measured reflections | l = −17→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.3361P] where P = (Fo2 + 2Fc2)/3 |
3341 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 1.71 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[Ag2(C6H6N2O)4](NO3)2 | γ = 111.360 (3)° |
Mr = 828.27 | V = 738.38 (16) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.2913 (10) Å | Mo Kα radiation |
b = 8.3395 (10) Å | µ = 1.40 mm−1 |
c = 13.1415 (17) Å | T = 293 K |
α = 92.934 (4)° | 0.24 × 0.21 × 0.17 mm |
β = 95.008 (4)° |
Rigaku R-AXIS RAPID IP diffractometer | 3341 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2896 reflections with I > 2σ(I) |
Tmin = 0.730, Tmax = 0.797 | Rint = 0.035 |
7293 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.11 | Δρmax = 1.71 e Å−3 |
3341 reflections | Δρmin = −0.34 e Å−3 |
210 parameters |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.38614 (4) | 0.61092 (3) | 0.314850 (18) | 0.04700 (13) | |
O1 | 1.0366 (4) | 0.7195 (3) | 0.7651 (2) | 0.0501 (6) | |
H1 | 1.0758 | 0.6378 | 0.7541 | 0.075* | |
O2 | 0.9485 (4) | 1.1845 (3) | −0.0856 (2) | 0.0522 (6) | |
H2 | 0.9451 | 1.2272 | −0.1419 | 0.078* | |
O3 | 0.7359 (7) | 0.5156 (5) | 0.3151 (4) | 0.1102 (16) | |
O4 | 1.0106 (5) | 0.6444 (5) | 0.2602 (3) | 0.0751 (10) | |
O5 | 0.8581 (6) | 0.7867 (4) | 0.3354 (3) | 0.0792 (10) | |
N1 | 0.4261 (4) | 0.7161 (4) | 0.4767 (2) | 0.0393 (6) | |
N2 | 0.8633 (4) | 0.6911 (4) | 0.7003 (2) | 0.0426 (6) | |
N3 | 0.4227 (4) | 0.6552 (4) | 0.1507 (2) | 0.0393 (6) | |
N4 | 0.7795 (4) | 1.0353 (4) | −0.0856 (2) | 0.0411 (6) | |
N5 | 0.8690 (4) | 0.6504 (4) | 0.3059 (2) | 0.0436 (7) | |
C1 | 0.2918 (5) | 0.5528 (4) | 0.0748 (3) | 0.0420 (7) | |
H1A | 0.1875 | 0.4574 | 0.0915 | 0.050* | |
C2 | 0.3047 (5) | 0.5827 (4) | −0.0277 (3) | 0.0438 (7) | |
H2A | 0.2104 | 0.5087 | −0.0783 | 0.053* | |
C3 | 0.4576 (5) | 0.7221 (4) | −0.0537 (3) | 0.0410 (7) | |
H3 | 0.4689 | 0.7437 | −0.1220 | 0.049* | |
C4 | 0.5962 (5) | 0.8315 (4) | 0.0240 (2) | 0.0354 (6) | |
C5 | 0.5728 (5) | 0.7911 (4) | 0.1242 (2) | 0.0366 (6) | |
H5 | 0.6663 | 0.8621 | 0.1762 | 0.044* | |
C6 | 0.7622 (5) | 0.9865 (4) | 0.0046 (3) | 0.0375 (7) | |
H6 | 0.8559 | 1.0499 | 0.0586 | 0.045* | |
C7 | 0.3097 (5) | 0.7957 (4) | 0.5116 (3) | 0.0430 (7) | |
H7 | 0.1944 | 0.7853 | 0.4708 | 0.052* | |
C8 | 0.3541 (5) | 0.8913 (4) | 0.6046 (3) | 0.0429 (7) | |
H8 | 0.2721 | 0.9467 | 0.6256 | 0.051* | |
C9 | 0.5228 (5) | 0.9041 (4) | 0.6669 (3) | 0.0407 (7) | |
H9 | 0.5570 | 0.9704 | 0.7296 | 0.049* | |
C10 | 0.6402 (5) | 0.8177 (4) | 0.6350 (2) | 0.0361 (6) | |
C11 | 0.5871 (5) | 0.7270 (4) | 0.5384 (2) | 0.0369 (6) | |
H11 | 0.6675 | 0.6713 | 0.5156 | 0.044* | |
C12 | 0.8170 (5) | 0.8228 (4) | 0.6996 (2) | 0.0396 (7) | |
H12 | 0.8952 | 0.9234 | 0.7401 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.05390 (19) | 0.0543 (2) | 0.03057 (17) | 0.01848 (14) | 0.00080 (12) | 0.00222 (11) |
O1 | 0.0459 (13) | 0.0570 (15) | 0.0475 (15) | 0.0220 (12) | −0.0050 (11) | 0.0026 (11) |
O2 | 0.0459 (13) | 0.0490 (14) | 0.0565 (16) | 0.0103 (11) | 0.0045 (12) | 0.0153 (12) |
O3 | 0.101 (3) | 0.062 (2) | 0.155 (5) | 0.007 (2) | 0.035 (3) | 0.043 (3) |
O4 | 0.0682 (19) | 0.124 (3) | 0.062 (2) | 0.064 (2) | 0.0219 (16) | 0.034 (2) |
O5 | 0.100 (3) | 0.0675 (19) | 0.079 (2) | 0.0441 (19) | 0.009 (2) | −0.0041 (16) |
N1 | 0.0458 (14) | 0.0412 (14) | 0.0277 (13) | 0.0131 (12) | 0.0010 (11) | 0.0040 (10) |
N2 | 0.0430 (14) | 0.0408 (14) | 0.0401 (15) | 0.0129 (12) | −0.0037 (12) | 0.0043 (11) |
N3 | 0.0400 (14) | 0.0462 (15) | 0.0333 (14) | 0.0179 (12) | 0.0039 (11) | 0.0034 (11) |
N4 | 0.0401 (14) | 0.0401 (14) | 0.0439 (16) | 0.0154 (12) | 0.0063 (12) | 0.0039 (12) |
N5 | 0.0483 (16) | 0.0521 (17) | 0.0383 (15) | 0.0257 (15) | 0.0081 (13) | 0.0138 (13) |
C1 | 0.0393 (16) | 0.0407 (17) | 0.0425 (18) | 0.0106 (14) | 0.0054 (14) | 0.0021 (13) |
C2 | 0.0442 (17) | 0.0446 (17) | 0.0386 (18) | 0.0150 (15) | −0.0037 (14) | −0.0056 (14) |
C3 | 0.0471 (18) | 0.0475 (18) | 0.0297 (15) | 0.0197 (15) | 0.0012 (14) | 0.0024 (13) |
C4 | 0.0349 (14) | 0.0415 (16) | 0.0328 (15) | 0.0178 (13) | 0.0035 (12) | 0.0027 (12) |
C5 | 0.0352 (15) | 0.0437 (16) | 0.0310 (15) | 0.0163 (13) | −0.0002 (12) | −0.0023 (12) |
C6 | 0.0367 (15) | 0.0424 (16) | 0.0373 (17) | 0.0203 (14) | 0.0013 (13) | 0.0012 (13) |
C7 | 0.0394 (16) | 0.0468 (17) | 0.0443 (19) | 0.0166 (15) | 0.0061 (14) | 0.0098 (14) |
C8 | 0.0470 (17) | 0.0457 (18) | 0.0413 (18) | 0.0210 (15) | 0.0138 (15) | 0.0082 (14) |
C9 | 0.0530 (19) | 0.0390 (16) | 0.0322 (16) | 0.0188 (15) | 0.0093 (14) | 0.0022 (12) |
C10 | 0.0424 (16) | 0.0309 (14) | 0.0319 (15) | 0.0097 (13) | 0.0039 (13) | 0.0057 (11) |
C11 | 0.0439 (16) | 0.0315 (14) | 0.0356 (16) | 0.0141 (13) | 0.0066 (13) | 0.0021 (12) |
C12 | 0.0455 (17) | 0.0385 (16) | 0.0315 (16) | 0.0129 (14) | 0.0015 (13) | −0.0022 (12) |
Ag1—N1 | 2.212 (3) | C2—C3 | 1.369 (5) |
Ag1—N3 | 2.229 (3) | C2—H2A | 0.9300 |
Ag1—N2i | 2.498 (3) | C3—C4 | 1.396 (5) |
O1—N2 | 1.397 (4) | C3—H3 | 0.9300 |
O1—H1 | 0.8400 | C4—C5 | 1.385 (4) |
O2—N4 | 1.396 (4) | C4—C6 | 1.466 (5) |
O2—H2 | 0.8400 | C5—H5 | 0.9300 |
O3—N5 | 1.208 (5) | C6—H6 | 0.9300 |
O4—N5 | 1.255 (4) | C7—C8 | 1.370 (5) |
O5—N5 | 1.214 (4) | C7—H7 | 0.9300 |
N1—C11 | 1.339 (4) | C8—C9 | 1.383 (5) |
N1—C7 | 1.349 (5) | C8—H8 | 0.9300 |
N2—C12 | 1.262 (4) | C9—C10 | 1.381 (5) |
N2—Ag1i | 2.498 (3) | C9—H9 | 0.9300 |
N3—C1 | 1.337 (5) | C10—C11 | 1.392 (4) |
N3—C5 | 1.344 (4) | C10—C12 | 1.466 (5) |
N4—C6 | 1.274 (4) | C11—H11 | 0.9300 |
C1—C2 | 1.387 (5) | C12—H12 | 0.9300 |
C1—H1A | 0.9300 | ||
N1—Ag1—N3 | 149.49 (11) | C5—C4—C3 | 117.7 (3) |
N1—Ag1—N2i | 107.79 (10) | C5—C4—C6 | 119.0 (3) |
N3—Ag1—N2i | 101.48 (10) | C3—C4—C6 | 123.3 (3) |
N2—O1—H1 | 109.5 | N3—C5—C4 | 123.8 (3) |
N4—O2—H2 | 109.5 | N3—C5—H5 | 118.1 |
C11—N1—C7 | 117.6 (3) | C4—C5—H5 | 118.1 |
C11—N1—Ag1 | 119.9 (2) | N4—C6—C4 | 120.7 (3) |
C7—N1—Ag1 | 121.6 (2) | N4—C6—H6 | 119.6 |
C12—N2—O1 | 112.4 (3) | C4—C6—H6 | 119.6 |
C12—N2—Ag1i | 123.3 (2) | N1—C7—C8 | 122.8 (3) |
O1—N2—Ag1i | 115.10 (18) | N1—C7—H7 | 118.6 |
C1—N3—C5 | 117.2 (3) | C8—C7—H7 | 118.6 |
C1—N3—Ag1 | 121.6 (2) | C7—C8—C9 | 119.0 (3) |
C5—N3—Ag1 | 121.1 (2) | C7—C8—H8 | 120.5 |
C6—N4—O2 | 110.6 (3) | C9—C8—H8 | 120.5 |
O3—N5—O5 | 120.1 (4) | C10—C9—C8 | 119.5 (3) |
O3—N5—O4 | 117.9 (4) | C10—C9—H9 | 120.3 |
O5—N5—O4 | 121.9 (4) | C8—C9—H9 | 120.3 |
N3—C1—C2 | 122.8 (3) | C9—C10—C11 | 117.8 (3) |
N3—C1—H1A | 118.6 | C9—C10—C12 | 121.5 (3) |
C2—C1—H1A | 118.6 | C11—C10—C12 | 120.6 (3) |
C3—C2—C1 | 119.4 (3) | N1—C11—C10 | 123.3 (3) |
C3—C2—H2A | 120.3 | N1—C11—H11 | 118.4 |
C1—C2—H2A | 120.3 | C10—C11—H11 | 118.4 |
C2—C3—C4 | 119.0 (3) | N2—C12—C10 | 120.1 (3) |
C2—C3—H3 | 120.5 | N2—C12—H12 | 119.9 |
C4—C3—H3 | 120.5 | C10—C12—H12 | 119.9 |
N3—Ag1—N1—C11 | −93.9 (3) | O2—N4—C6—C4 | −179.6 (3) |
N2i—Ag1—N1—C11 | 103.1 (2) | C5—C4—C6—N4 | −174.4 (3) |
N3—Ag1—N1—C7 | 75.2 (3) | C3—C4—C6—N4 | 4.9 (5) |
N2i—Ag1—N1—C7 | −87.8 (3) | C11—N1—C7—C8 | 2.6 (5) |
N1—Ag1—N3—C1 | −147.5 (3) | Ag1—N1—C7—C8 | −166.8 (2) |
N2i—Ag1—N3—C1 | 16.0 (3) | N1—C7—C8—C9 | −1.5 (5) |
N1—Ag1—N3—C5 | 29.4 (4) | C7—C8—C9—C10 | −1.4 (5) |
N2i—Ag1—N3—C5 | −167.1 (2) | C8—C9—C10—C11 | 2.9 (4) |
C5—N3—C1—C2 | −0.6 (5) | C8—C9—C10—C12 | −178.1 (3) |
Ag1—N3—C1—C2 | 176.4 (3) | C7—N1—C11—C10 | −0.9 (5) |
N3—C1—C2—C3 | 0.2 (5) | Ag1—N1—C11—C10 | 168.7 (2) |
C1—C2—C3—C4 | −0.4 (5) | C9—C10—C11—N1 | −1.8 (5) |
C2—C3—C4—C5 | 0.9 (5) | C12—C10—C11—N1 | 179.2 (3) |
C2—C3—C4—C6 | −178.4 (3) | O1—N2—C12—C10 | 179.4 (3) |
C1—N3—C5—C4 | 1.2 (5) | Ag1i—N2—C12—C10 | −35.6 (4) |
Ag1—N3—C5—C4 | −175.8 (2) | C9—C10—C12—N2 | 144.0 (3) |
C3—C4—C5—N3 | −1.4 (5) | C11—C10—C12—N2 | −37.1 (5) |
C6—C4—C5—N3 | 178.0 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3ii | 0.84 | 2.39 | 3.189 (6) | 158 |
O1—H1···O4ii | 0.84 | 2.20 | 2.925 (5) | 145 |
O2—H2···O4iii | 0.84 | 1.92 | 2.745 (4) | 169 |
Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C6H6N2O)4](NO3)2 |
Mr | 828.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.2913 (10), 8.3395 (10), 13.1415 (17) |
α, β, γ (°) | 92.934 (4), 95.008 (4), 111.360 (3) |
V (Å3) | 738.38 (16) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.24 × 0.21 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.730, 0.797 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7293, 3341, 2896 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.107, 1.11 |
No. of reflections | 3341 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.71, −0.34 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.84 | 2.39 | 3.189 (6) | 158.3 |
O1—H1···O4i | 0.84 | 2.20 | 2.925 (5) | 145.0 |
O2—H2···O4ii | 0.84 | 1.92 | 2.745 (4) | 168.6 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+2, −z. |
Acknowledgements
We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.
References
Abu-Youssef, M. A., Soliman, S. V., Langer, V., Gohar, Y. M., Hasanen, A. A., Makhyoun, M. A., Zaky, A. H. & Öhrström, L. R. (2010). Inorg. Chem. 49, 9788–9797. Web of Science CAS PubMed Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, J., Gao, S., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, m735–m736. CSD CrossRef IUCr Journals Google Scholar
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A previous study on the adducts of silver salts with nicotinylaldehyde oxime reported the salt, [Ag(C6H6N2O)2] ClO4; the metal atom shows linear coordination (Xu et al., 2012). The aromatic amine-coordinated AgI atom in dinuclear [Ag(C6H6N2O)2]2 2NO3 is bridged by another hydroxylamine molecule that uses its aromatic and oxime N atoms for bridging, and it exists in a trigonal planar geometry (Scheme I, Fig. 1). The hydroxyl OH groups forms H atoms to the nitrate O atoms of adjacent molecules to generate a chain running along the shortest axis of the orthorhombic unit cell (Table 1).
With picolinylaldehyde oxime in place of nicotinylaldehyde oxime, the synthesis yields the monomeric adduct in which the metal atom is chelated by the ligand (Abu-Youssef et al., 2010).