metal-organic compounds
Poly[[[μ3-(E)-N-(pyridin-4-ylmethylidene)hydroxylaminato-κ3O:N:N′][μ2-(E)-N-(pyridin-4-ylmethylidene)hydroxylamine-κ2N:N′][(E)-N-(pyridin-4-ylmethylidene-κN)hydroxylamine]disilver(I)] nitrate]
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
The title coordination polymer, {[Ag2(C6H5N2O)(C6H6N2O)2]NO3}n, features a deprotonated N-(pyridin-4-ylmethylidene)hydroxylaminate anion and two neutral N-(pyridin-4-ylmethylidene)hydroxylamine molecules in the The anion connects three AgI atoms through its O and two N-donor atoms. One neutral ligand functions in a monodentate mode; the other functions in a bridging mode, binding though its two N atoms. The coordination geometry of the two independent metal atoms is T-shaped; the manner of bridging gives rise to a layer motif parallel to (100). In the crystal, the nitrate ion is disordered over two positions in a 1:1 ratio, and is sandwiched between adjacent layers. O—H⋯O hydrogen bonding is present between nitrate ions and layers, and also between adjacent layers.
Related literature
For mononuclear (Nitrato-κ2O,O′)bis[(E)-N-(pyridin-4-ylmethylidene-κN)hydroxyamine]silver(I), see: Gao & Ng (2012).
Experimental
Crystal data
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Refinement
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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/S1600536812046090/xu5648sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046090/xu5648Isup2.hkl
Isonicotinaldehyde oxime was synthesized from the reaction of isonicotinaldehyde and hydroxylamine. Silver nitrate (1 mmol) dissolved in water (5 ml) was added to picolinaldehyde oxime (1 mmol) dissolved in ethanol (5 ml). Several drops of ammonium hydroxide were added. 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 nitrate ion is disordered over two positions in a 1:1 ratio. Nitrogen–oxygen distances were restrained to 1.24±0.01 A and oxygen···oxygen contacts to 2.15±0.01 Å. For each component, the temperature factors of the O atoms were made identical. The temperature factors of the N atoms of the two components were made identical too. The isotropic temperature factors were tightly restrained.
The (3 9 9), (-7 10 13) and (-3 7 18) reflections were omitted.
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).[Ag2(C6H5N2O)(C6H6N2O)2]NO3 | F(000) = 1264 |
Mr = 643.13 | Dx = 1.931 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10662 reflections |
a = 13.1628 (18) Å | θ = 3.1–27.5° |
b = 10.9926 (18) Å | µ = 1.82 mm−1 |
c = 16.315 (2) Å | T = 293 K |
β = 110.412 (4)° | Prism, colorless |
V = 2212.4 (6) Å3 | 0.20 × 0.12 × 0.12 mm |
Z = 4 |
Rigaku R-AXIS RAPID IP diffractometer | 5047 independent reflections |
Radiation source: fine-focus sealed tube | 3355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scan | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −17→17 |
Tmin = 0.712, Tmax = 0.811 | k = −14→14 |
21226 measured reflections | l = −19→21 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3 |
5047 reflections | (Δ/σ)max = 0.001 |
306 parameters | Δρmax = 0.77 e Å−3 |
26 restraints | Δρmin = −0.43 e Å−3 |
[Ag2(C6H5N2O)(C6H6N2O)2]NO3 | V = 2212.4 (6) Å3 |
Mr = 643.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1628 (18) Å | µ = 1.82 mm−1 |
b = 10.9926 (18) Å | T = 293 K |
c = 16.315 (2) Å | 0.20 × 0.12 × 0.12 mm |
β = 110.412 (4)° |
Rigaku R-AXIS RAPID IP diffractometer | 5047 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3355 reflections with I > 2σ(I) |
Tmin = 0.712, Tmax = 0.811 | Rint = 0.047 |
21226 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 26 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.77 e Å−3 |
5047 reflections | Δρmin = −0.43 e Å−3 |
306 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.82406 (3) | 0.44988 (5) | 0.68283 (2) | 0.0906 (2) | |
Ag2 | 0.45572 (3) | 0.01686 (3) | 0.114909 (19) | 0.06273 (15) | |
O1 | 0.6234 (2) | 0.4403 (3) | 0.57575 (15) | 0.0523 (6) | |
O2 | 1.0680 (3) | 0.1718 (4) | 0.3037 (2) | 0.1041 (13) | |
H2 | 1.0946 | 0.1023 | 0.3041 | 0.156* | |
O3 | 0.6612 (3) | 0.8349 (3) | 1.07189 (16) | 0.0633 (8) | |
H3 | 0.6532 | 0.9104 | 1.0744 | 0.095* | |
O4 | 1.1249 (5) | −0.0582 (8) | 0.3006 (6) | 0.1012 (16) | 0.50 |
O5 | 1.2395 (7) | −0.1874 (9) | 0.2869 (8) | 0.1012 (16) | 0.50 |
O6 | 1.2906 (5) | −0.0465 (7) | 0.3833 (5) | 0.1012 (16) | 0.50 |
O4' | 1.1788 (14) | −0.0670 (13) | 0.3637 (8) | 0.187 (4) | 0.50 |
O5' | 1.2614 (15) | −0.1635 (11) | 0.2915 (11) | 0.187 (4) | 0.50 |
O6' | 1.2181 (13) | 0.0236 (10) | 0.2655 (8) | 0.187 (4) | 0.50 |
N1 | 0.5108 (3) | 0.0936 (3) | 0.24501 (19) | 0.0556 (8) | |
N2 | 0.6020 (2) | 0.3906 (3) | 0.49497 (17) | 0.0460 (7) | |
N3 | 0.8829 (3) | 0.3913 (4) | 0.5817 (2) | 0.0707 (11) | |
N4 | 1.0390 (3) | 0.1859 (5) | 0.3770 (2) | 0.0763 (12) | |
N5 | 0.7900 (3) | 0.5396 (4) | 0.7881 (2) | 0.0676 (10) | |
N6 | 0.6741 (3) | 0.8056 (3) | 0.99397 (19) | 0.0522 (8) | |
N7 | 1.2216 (8) | −0.0974 (7) | 0.3251 (6) | 0.0797 (19) | 0.50 |
N7' | 1.2207 (7) | −0.0713 (10) | 0.3065 (6) | 0.0797 (19) | 0.50 |
C1 | 0.5737 (3) | 0.1916 (4) | 0.2613 (2) | 0.0578 (10) | |
H1 | 0.5978 | 0.2198 | 0.2175 | 0.069* | |
C2 | 0.6052 (3) | 0.2537 (4) | 0.3395 (2) | 0.0553 (9) | |
H2A | 0.6491 | 0.3223 | 0.3475 | 0.066* | |
C3 | 0.5710 (3) | 0.2131 (4) | 0.4062 (2) | 0.0510 (9) | |
C4 | 0.5075 (4) | 0.1096 (4) | 0.3898 (2) | 0.0589 (10) | |
H4 | 0.4840 | 0.0783 | 0.4331 | 0.071* | |
C5 | 0.4786 (4) | 0.0526 (4) | 0.3098 (3) | 0.0627 (11) | |
H5 | 0.4354 | −0.0166 | 0.3001 | 0.075* | |
C6 | 0.5966 (3) | 0.2758 (4) | 0.4903 (2) | 0.0536 (9) | |
H6 | 0.6089 | 0.2305 | 0.5410 | 0.064* | |
C7 | 0.9441 (4) | 0.2916 (5) | 0.5886 (3) | 0.0783 (14) | |
H7 | 0.9633 | 0.2467 | 0.6401 | 0.094* | |
C8 | 0.9799 (4) | 0.2525 (5) | 0.5230 (3) | 0.0720 (13) | |
H8 | 1.0224 | 0.1830 | 0.5305 | 0.086* | |
C9 | 0.9516 (3) | 0.3179 (4) | 0.4458 (3) | 0.0614 (11) | |
C10 | 0.8877 (3) | 0.4200 (5) | 0.4382 (3) | 0.0651 (11) | |
H10 | 0.8670 | 0.4666 | 0.3874 | 0.078* | |
C11 | 0.8553 (4) | 0.4518 (5) | 0.5069 (3) | 0.0701 (13) | |
H11 | 0.8114 | 0.5200 | 0.5005 | 0.084* | |
C12 | 0.9898 (4) | 0.2858 (5) | 0.3741 (3) | 0.0706 (12) | |
H12 | 0.9781 | 0.3383 | 0.3270 | 0.085* | |
C13 | 0.7989 (4) | 0.4791 (5) | 0.8613 (3) | 0.0721 (13) | |
H13 | 0.8249 | 0.3997 | 0.8674 | 0.087* | |
C14 | 0.7717 (4) | 0.5284 (4) | 0.9274 (3) | 0.0623 (11) | |
H14 | 0.7795 | 0.4827 | 0.9772 | 0.075* | |
C15 | 0.7327 (3) | 0.6453 (4) | 0.9210 (2) | 0.0528 (9) | |
C16 | 0.7235 (3) | 0.7088 (4) | 0.8454 (2) | 0.0642 (11) | |
H16 | 0.6980 | 0.7885 | 0.8378 | 0.077* | |
C17 | 0.7525 (4) | 0.6524 (5) | 0.7817 (3) | 0.0730 (13) | |
H17 | 0.7454 | 0.6960 | 0.7311 | 0.088* | |
C18 | 0.7078 (3) | 0.6971 (4) | 0.9947 (2) | 0.0563 (10) | |
H18 | 0.7171 | 0.6489 | 1.0437 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0834 (3) | 0.1332 (5) | 0.0585 (2) | 0.0248 (2) | 0.0289 (2) | −0.0216 (2) |
Ag2 | 0.0788 (3) | 0.0733 (3) | 0.03828 (19) | −0.01131 (17) | 0.02310 (17) | −0.01213 (14) |
O1 | 0.0644 (15) | 0.0577 (17) | 0.0356 (13) | −0.0003 (13) | 0.0187 (12) | −0.0058 (12) |
O2 | 0.111 (3) | 0.147 (4) | 0.067 (2) | 0.034 (3) | 0.046 (2) | −0.015 (2) |
O3 | 0.0896 (19) | 0.066 (2) | 0.0418 (14) | 0.0126 (17) | 0.0320 (14) | 0.0045 (13) |
O4 | 0.079 (3) | 0.101 (4) | 0.109 (3) | 0.025 (2) | 0.014 (3) | −0.034 (3) |
O5 | 0.079 (3) | 0.101 (4) | 0.109 (3) | 0.025 (2) | 0.014 (3) | −0.034 (3) |
O6 | 0.079 (3) | 0.101 (4) | 0.109 (3) | 0.025 (2) | 0.014 (3) | −0.034 (3) |
O4' | 0.258 (10) | 0.189 (9) | 0.143 (6) | 0.063 (7) | 0.107 (7) | 0.017 (6) |
O5' | 0.258 (10) | 0.189 (9) | 0.143 (6) | 0.063 (7) | 0.107 (7) | 0.017 (6) |
O6' | 0.258 (10) | 0.189 (9) | 0.143 (6) | 0.063 (7) | 0.107 (7) | 0.017 (6) |
N1 | 0.069 (2) | 0.062 (2) | 0.0371 (16) | −0.0044 (18) | 0.0200 (15) | −0.0061 (15) |
N2 | 0.0533 (16) | 0.054 (2) | 0.0300 (14) | 0.0030 (15) | 0.0140 (13) | −0.0019 (13) |
N3 | 0.064 (2) | 0.093 (3) | 0.054 (2) | 0.009 (2) | 0.0206 (18) | −0.014 (2) |
N4 | 0.072 (2) | 0.105 (4) | 0.055 (2) | 0.009 (2) | 0.0257 (19) | −0.019 (2) |
N5 | 0.071 (2) | 0.086 (3) | 0.047 (2) | 0.012 (2) | 0.0214 (18) | −0.0107 (19) |
N6 | 0.0588 (18) | 0.061 (2) | 0.0401 (16) | −0.0009 (16) | 0.0212 (15) | −0.0022 (15) |
N7 | 0.098 (3) | 0.102 (5) | 0.050 (4) | 0.016 (3) | 0.039 (3) | 0.003 (3) |
N7' | 0.098 (3) | 0.102 (5) | 0.050 (4) | 0.016 (3) | 0.039 (3) | 0.003 (3) |
C1 | 0.076 (3) | 0.061 (3) | 0.042 (2) | −0.006 (2) | 0.027 (2) | −0.0037 (18) |
C2 | 0.068 (2) | 0.052 (2) | 0.046 (2) | −0.006 (2) | 0.0211 (19) | −0.0028 (18) |
C3 | 0.065 (2) | 0.049 (2) | 0.0373 (17) | 0.0062 (19) | 0.0171 (17) | −0.0002 (16) |
C4 | 0.082 (3) | 0.058 (3) | 0.042 (2) | −0.005 (2) | 0.027 (2) | 0.0007 (18) |
C5 | 0.085 (3) | 0.058 (3) | 0.051 (2) | −0.014 (2) | 0.030 (2) | −0.009 (2) |
C6 | 0.072 (2) | 0.053 (3) | 0.0359 (18) | 0.007 (2) | 0.0188 (18) | 0.0028 (17) |
C7 | 0.083 (3) | 0.098 (4) | 0.053 (2) | 0.020 (3) | 0.023 (2) | −0.002 (3) |
C8 | 0.068 (3) | 0.088 (4) | 0.059 (2) | 0.015 (2) | 0.022 (2) | −0.008 (3) |
C9 | 0.048 (2) | 0.081 (3) | 0.055 (2) | −0.002 (2) | 0.0171 (19) | −0.012 (2) |
C10 | 0.057 (2) | 0.083 (3) | 0.057 (2) | 0.007 (2) | 0.022 (2) | −0.003 (2) |
C11 | 0.057 (2) | 0.078 (3) | 0.072 (3) | 0.010 (2) | 0.018 (2) | −0.014 (3) |
C12 | 0.068 (3) | 0.088 (4) | 0.057 (3) | 0.008 (3) | 0.023 (2) | −0.007 (2) |
C13 | 0.077 (3) | 0.068 (3) | 0.072 (3) | 0.011 (2) | 0.027 (3) | −0.011 (2) |
C14 | 0.080 (3) | 0.060 (3) | 0.052 (2) | 0.003 (2) | 0.028 (2) | 0.004 (2) |
C15 | 0.050 (2) | 0.062 (3) | 0.046 (2) | −0.0010 (18) | 0.0171 (17) | −0.0025 (19) |
C16 | 0.074 (3) | 0.073 (3) | 0.046 (2) | 0.016 (2) | 0.021 (2) | 0.002 (2) |
C17 | 0.085 (3) | 0.092 (4) | 0.043 (2) | 0.015 (3) | 0.023 (2) | 0.002 (2) |
C18 | 0.069 (2) | 0.061 (3) | 0.042 (2) | 0.002 (2) | 0.0229 (19) | 0.0016 (18) |
Ag1—O1 | 2.612 (3) | C1—H1 | 0.9300 |
Ag1—N3 | 2.151 (3) | C2—C3 | 1.389 (5) |
Ag1—N5 | 2.158 (3) | C2—H2A | 0.9300 |
Ag2—O1i | 2.546 (2) | C3—C4 | 1.382 (6) |
Ag2—N1 | 2.161 (3) | C3—C6 | 1.466 (5) |
Ag2—N2ii | 2.183 (3) | C4—C5 | 1.377 (5) |
O1—N2 | 1.362 (3) | C4—H4 | 0.9300 |
O1—Ag2iii | 2.546 (2) | C5—H5 | 0.9300 |
O2—N4 | 1.387 (4) | C6—H6 | 0.9300 |
O2—H2 | 0.8400 | C7—C8 | 1.381 (6) |
O3—N6 | 1.378 (4) | C7—H7 | 0.9300 |
O3—H3 | 0.8400 | C8—C9 | 1.383 (6) |
O4—N7 | 1.270 (9) | C8—H8 | 0.9300 |
O5—N7 | 1.234 (6) | C9—C10 | 1.381 (6) |
O6—N7 | 1.199 (11) | C9—C12 | 1.469 (6) |
O4'—N7' | 1.239 (7) | C10—C11 | 1.377 (6) |
O5'—N7' | 1.211 (8) | C10—H10 | 0.9300 |
O6'—N7' | 1.234 (8) | C11—H11 | 0.9300 |
N1—C1 | 1.327 (5) | C12—H12 | 0.9300 |
N1—C5 | 1.346 (5) | C13—C14 | 1.362 (6) |
N2—C6 | 1.264 (5) | C13—H13 | 0.9300 |
N2—Ag2iv | 2.183 (3) | C14—C15 | 1.374 (6) |
N3—C11 | 1.324 (6) | C14—H14 | 0.9300 |
N3—C7 | 1.342 (6) | C15—C16 | 1.386 (5) |
N4—C12 | 1.267 (6) | C15—C18 | 1.467 (5) |
N5—C17 | 1.325 (6) | C16—C17 | 1.374 (6) |
N5—C13 | 1.337 (6) | C16—H16 | 0.9300 |
N6—C18 | 1.271 (5) | C17—H17 | 0.9300 |
C1—C2 | 1.378 (5) | C18—H18 | 0.9300 |
N3—Ag1—N5 | 167.71 (16) | N1—C5—C4 | 122.3 (4) |
N3—Ag1—O1 | 91.45 (11) | N1—C5—H5 | 118.9 |
N5—Ag1—O1 | 96.21 (12) | C4—C5—H5 | 118.9 |
N1—Ag2—N2ii | 162.98 (12) | N2—C6—C3 | 121.0 (3) |
N1—Ag2—O1i | 98.67 (10) | N2—C6—H6 | 119.5 |
N2ii—Ag2—O1i | 89.75 (9) | C3—C6—H6 | 119.5 |
N2—O1—Ag2iii | 114.36 (19) | N3—C7—C8 | 123.1 (5) |
N2—O1—Ag1 | 118.84 (18) | N3—C7—H7 | 118.5 |
Ag2iii—O1—Ag1 | 125.99 (9) | C8—C7—H7 | 118.5 |
N4—O2—H2 | 109.5 | C7—C8—C9 | 119.2 (5) |
N6—O3—H3 | 109.5 | C7—C8—H8 | 120.4 |
C1—N1—C5 | 117.4 (3) | C9—C8—H8 | 120.4 |
C1—N1—Ag2 | 119.0 (2) | C10—C9—C8 | 117.8 (4) |
C5—N1—Ag2 | 123.4 (3) | C10—C9—C12 | 119.4 (4) |
C6—N2—O1 | 116.5 (3) | C8—C9—C12 | 122.8 (4) |
C6—N2—Ag2iv | 126.0 (3) | C11—C10—C9 | 119.0 (4) |
O1—N2—Ag2iv | 115.8 (2) | C11—C10—H10 | 120.5 |
C11—N3—C7 | 116.9 (4) | C9—C10—H10 | 120.5 |
C11—N3—Ag1 | 120.0 (3) | N3—C11—C10 | 124.0 (4) |
C7—N3—Ag1 | 123.1 (3) | N3—C11—H11 | 118.0 |
C12—N4—O2 | 110.8 (4) | C10—C11—H11 | 118.0 |
C17—N5—C13 | 116.7 (4) | N4—C12—C9 | 119.4 (5) |
C17—N5—Ag1 | 122.7 (3) | N4—C12—H12 | 120.3 |
C13—N5—Ag1 | 120.4 (3) | C9—C12—H12 | 120.3 |
C18—N6—O3 | 111.4 (3) | N5—C13—C14 | 123.0 (5) |
O6—N7—O5 | 123.3 (8) | N5—C13—H13 | 118.5 |
O6—N7—O4 | 119.3 (7) | C14—C13—H13 | 118.5 |
O5—N7—O4 | 117.4 (9) | C13—C14—C15 | 120.4 (4) |
O5'—N7'—O6' | 121.9 (8) | C13—C14—H14 | 119.8 |
O5'—N7'—O4' | 122.0 (9) | C15—C14—H14 | 119.8 |
O6'—N7'—O4' | 116.2 (8) | C14—C15—C16 | 117.0 (4) |
N1—C1—C2 | 123.6 (3) | C14—C15—C18 | 119.0 (4) |
N1—C1—H1 | 118.2 | C16—C15—C18 | 124.0 (4) |
C2—C1—H1 | 118.2 | C17—C16—C15 | 119.0 (4) |
C1—C2—C3 | 119.4 (4) | C17—C16—H16 | 120.5 |
C1—C2—H2A | 120.3 | C15—C16—H16 | 120.5 |
C3—C2—H2A | 120.3 | N5—C17—C16 | 123.9 (4) |
C4—C3—C2 | 117.0 (3) | N5—C17—H17 | 118.1 |
C4—C3—C6 | 119.6 (3) | C16—C17—H17 | 118.1 |
C2—C3—C6 | 123.4 (4) | N6—C18—C15 | 122.2 (4) |
C5—C4—C3 | 120.4 (3) | N6—C18—H18 | 118.9 |
C5—C4—H4 | 119.8 | C15—C18—H18 | 118.9 |
C3—C4—H4 | 119.8 | ||
N3—Ag1—O1—N2 | 8.3 (3) | O1—N2—C6—C3 | 178.3 (3) |
N5—Ag1—O1—N2 | 178.7 (2) | Ag2iv—N2—C6—C3 | 13.6 (5) |
N3—Ag1—O1—Ag2iii | 177.47 (17) | C4—C3—C6—N2 | −143.2 (4) |
N5—Ag1—O1—Ag2iii | −12.15 (17) | C2—C3—C6—N2 | 35.2 (6) |
N2ii—Ag2—N1—C1 | 153.9 (4) | C11—N3—C7—C8 | 1.2 (8) |
O1i—Ag2—N1—C1 | 35.0 (3) | Ag1—N3—C7—C8 | 178.5 (4) |
N2ii—Ag2—N1—C5 | −31.0 (6) | N3—C7—C8—C9 | −0.3 (8) |
O1i—Ag2—N1—C5 | −149.9 (3) | C7—C8—C9—C10 | −0.3 (7) |
Ag2iii—O1—N2—C6 | −88.6 (3) | C7—C8—C9—C12 | 177.4 (5) |
Ag1—O1—N2—C6 | 81.8 (3) | C8—C9—C10—C11 | 0.0 (7) |
Ag2iii—O1—N2—Ag2iv | 77.7 (2) | C12—C9—C10—C11 | −177.8 (4) |
Ag1—O1—N2—Ag2iv | −111.96 (18) | C7—N3—C11—C10 | −1.6 (7) |
N5—Ag1—N3—C11 | −73.7 (8) | Ag1—N3—C11—C10 | −179.0 (4) |
O1—Ag1—N3—C11 | 55.0 (4) | C9—C10—C11—N3 | 1.1 (7) |
N5—Ag1—N3—C7 | 109.0 (8) | O2—N4—C12—C9 | 179.7 (4) |
O1—Ag1—N3—C7 | −122.3 (4) | C10—C9—C12—N4 | −172.9 (4) |
N3—Ag1—N5—C17 | 61.9 (9) | C8—C9—C12—N4 | 9.5 (7) |
O1—Ag1—N5—C17 | −66.4 (4) | C17—N5—C13—C14 | −0.1 (7) |
N3—Ag1—N5—C13 | −122.9 (7) | Ag1—N5—C13—C14 | −175.6 (4) |
O1—Ag1—N5—C13 | 108.8 (4) | N5—C13—C14—C15 | 0.2 (8) |
C5—N1—C1—C2 | −1.4 (6) | C13—C14—C15—C16 | −0.4 (7) |
Ag2—N1—C1—C2 | 174.0 (3) | C13—C14—C15—C18 | −177.8 (4) |
N1—C1—C2—C3 | 0.4 (7) | C14—C15—C16—C17 | 0.5 (6) |
C1—C2—C3—C4 | 1.0 (6) | C18—C15—C16—C17 | 177.8 (4) |
C1—C2—C3—C6 | −177.4 (4) | C13—N5—C17—C16 | 0.2 (7) |
C2—C3—C4—C5 | −1.4 (6) | Ag1—N5—C17—C16 | 175.6 (4) |
C6—C3—C4—C5 | 177.1 (4) | C15—C16—C17—N5 | −0.4 (8) |
C1—N1—C5—C4 | 0.9 (7) | O3—N6—C18—C15 | −177.3 (3) |
Ag2—N1—C5—C4 | −174.2 (3) | C14—C15—C18—N6 | 178.2 (4) |
C3—C4—C5—N1 | 0.4 (7) | C16—C15—C18—N6 | 1.0 (7) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4 | 0.84 | 1.81 | 2.642 (9) | 169 |
O2—H2···O4′ | 0.84 | 2.21 | 2.997 (14) | 156 |
O3—H3···O1v | 0.84 | 1.69 | 2.527 (4) | 174 |
Symmetry code: (v) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C6H5N2O)(C6H6N2O)2]NO3 |
Mr | 643.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.1628 (18), 10.9926 (18), 16.315 (2) |
β (°) | 110.412 (4) |
V (Å3) | 2212.4 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.82 |
Crystal size (mm) | 0.20 × 0.12 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.712, 0.811 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21226, 5047, 3355 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.119, 1.07 |
No. of reflections | 5047 |
No. of parameters | 306 |
No. of restraints | 26 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.77, −0.43 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Ag1—O1 | 2.612 (3) | Ag2—O1i | 2.546 (2) |
Ag1—N3 | 2.151 (3) | Ag2—N1 | 2.161 (3) |
Ag1—N5 | 2.158 (3) | Ag2—N2ii | 2.183 (3) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4 | 0.84 | 1.81 | 2.642 (9) | 168.7 |
O2—H2···O4' | 0.84 | 2.21 | 2.997 (14) | 156.1 |
O3—H3···O1iii | 0.84 | 1.69 | 2.527 (4) | 174.1 |
Symmetry code: (iii) x, −y+3/2, z+1/2. |
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
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Gao, S. & Ng, S. W. (2012). Acta Cryst. E68, m1542. CSD CrossRef IUCr Journals 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
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The preceding report presents the crystal structure of bis(isonicotinylaldehyde oxide)(nitrato)silver (Gao & Ng, 2012). When some ammonium hydroxide was added to the reaction, the acid hydrogen of the isonicotinylaldehyde oxide is partially removed so that the product consists of a cation having two AgI atoms, one deprotonated ligand and two neutral ligands. The charge is balanced by a nitrate anion. The dinuclear cations are linked by coordination bonds into a polycation (Scheme I). The coordination polymer features a deprotonated N-(pyridin-4-ylmethylidene)hydroxylamine and two neutral N-(pyridin-4-ylmethylidene)hydroxylamine molecules. The anion connects three AgI atoms through its O and two N donor-atoms. One neutral ligand functions in a monodentate mode; the other functions in a bridging mode, binding though its two N atoms. The geometry of the two independent metal atoms is T-shaped (Fig. 1); the manner of bridge gives rise to a layer motif. The anion is sandwiched between adjacent layers (Fig. 2).