metal-organic compounds
Bis{μ-2-[(pyrimidin-2-yl)aminomethyl]phenolato}-κ2N1:O;κ2O:N1-bis({2-[(pyrimidin-2-yl-κN)aminomethyl]phenol}silver(I)) dihydrate
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 AgI atom in the title centrosymmetric dinuclear compound, [Ag2(C11H10N3O)2(C11H11N3O)2]·2H2O, shows a T-shaped coordination arising from bonding to the N atom of a neutral 2-[(pyrimidin-2-yl)aminomethyl]phenol ligand, the N atom of the 2-[(pyrimidin-2-yl)aminomethyl]phenolate anion [N—Ag—N = 171.8 (1)°] and the terminal O atom of the other anion [Ag—O = 2.606 (3) Å]. A pair of 2-[(pyrimidin-2-yl)aminomethyl]phenolate anions link the two AgI atoms to form the dinuclear compound. In the crystal, adjacent dinuclear molecules are linked to the lattice water molecules, generating an O—H⋯O- and N—H⋯O-connected three-dimensional network. In the crystal, the hydroxy H atom is disordered over two positions in a 1:1 ratio; one half-occupancy H atom is connected to one hydroxy group, whereas the other half-occupancy H atom is connected to another hydroxy group.
Related literature
For the structure of 2-{[(pyrimidin-2-yl)amino]methyl}phenol, see: Xu et al. (2011).
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/S1600536812045783/xu5644sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045783/xu5644Isup2.hkl
An acetonitrile solution (10 ml) of silver nitrate (1 mmol) was added to a methanol solution (5 ml) of 2-[(pyrimidin-2-yl)aminomethyl]phenol (1 mmol) and potassium hydroxide (0.5 mmol). The solution was filtered and then side aside, away from light, for the growth of crystals. Colorless crystals were obtained after several days.
Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2U(C). The amino and hydroxy/water H atoms were located in a difference Fouier map, and were refined with distance restraints of N–H 0.88±0.01, O–H 0.84±0.01 and H···H 1.37±0.01 Å. Their temperature factors were refined.The hydroxy H-atom is disordered over two positions in a 1:1 ratio; one half-occupancy H-atom is connected to O1 whereas the other half-occupancy atom is connected to O2.
The final difference Fouier map had a peak at 0.83 Å from Ag1 and a hole at 0.84 Å from this atom.
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 [Ag2(C11H10N3O)2(C11H11N3O)]2.H2O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the phenolic –OH groups is not shown. |
[Ag2(C11H10N3O)2(C11H11N3O)2]·2H2O | F(000) = 1072 |
Mr = 1054.67 | Dx = 1.631 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 13157 reflections |
a = 9.2992 (4) Å | θ = 3.1–27.5° |
b = 24.808 (1) Å | µ = 0.98 mm−1 |
c = 9.8158 (5) Å | T = 293 K |
β = 108.453 (1)° | Prism, colorless |
V = 2148.02 (17) Å3 | 0.23 × 0.20 × 0.17 mm |
Z = 2 |
Rigaku R-AXIS RAPID IP diffractometer | 4910 independent reflections |
Radiation source: fine-focus sealed tube | 3230 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ω scan | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→11 |
Tmin = 0.807, Tmax = 0.852 | k = −32→32 |
20943 measured reflections | l = −12→12 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0382P)2 + 4.7243P] where P = (Fo2 + 2Fc2)/3 |
4910 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 1.27 e Å−3 |
7 restraints | Δρmin = −1.29 e Å−3 |
[Ag2(C11H10N3O)2(C11H11N3O)2]·2H2O | V = 2148.02 (17) Å3 |
Mr = 1054.67 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.2992 (4) Å | µ = 0.98 mm−1 |
b = 24.808 (1) Å | T = 293 K |
c = 9.8158 (5) Å | 0.23 × 0.20 × 0.17 mm |
β = 108.453 (1)° |
Rigaku R-AXIS RAPID IP diffractometer | 4910 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3230 reflections with I > 2σ(I) |
Tmin = 0.807, Tmax = 0.852 | Rint = 0.063 |
20943 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 7 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 1.27 e Å−3 |
4910 reflections | Δρmin = −1.29 e Å−3 |
307 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.70167 (5) | 0.644035 (13) | 0.56817 (5) | 0.04905 (15) | |
O1 | 1.0721 (3) | 0.39077 (12) | 0.5102 (3) | 0.0383 (7) | |
H1O | 0.990 (7) | 0.376 (4) | 0.461 (10) | 0.057* | 0.50 |
O2 | 0.1768 (4) | 0.84419 (14) | 0.0994 (4) | 0.0458 (8) | |
H2O | 0.095 (7) | 0.858 (5) | 0.050 (11) | 0.069* | 0.50 |
O1W | 0.3708 (5) | 0.64557 (15) | 0.4170 (5) | 0.0650 (11) | |
H11 | 0.289 (4) | 0.659 (2) | 0.420 (8) | 0.097* | |
H12 | 0.353 (6) | 0.6145 (12) | 0.382 (7) | 0.097* | |
N1 | 0.8011 (4) | 0.51659 (14) | 0.5833 (4) | 0.0371 (9) | |
H1 | 0.838 (5) | 0.5460 (11) | 0.557 (5) | 0.045* | |
N2 | 0.6393 (4) | 0.56969 (14) | 0.6588 (4) | 0.0362 (8) | |
N3 | 0.6313 (4) | 0.47353 (14) | 0.6741 (4) | 0.0404 (9) | |
N4 | 0.7537 (4) | 0.72440 (15) | 0.5013 (5) | 0.0441 (10) | |
N5 | 0.7062 (5) | 0.80270 (15) | 0.3525 (5) | 0.0482 (10) | |
N6 | 0.5199 (4) | 0.73932 (15) | 0.3360 (5) | 0.0441 (10) | |
H6 | 0.487 (6) | 0.7108 (13) | 0.370 (5) | 0.053* | |
C1 | 0.5302 (5) | 0.57248 (19) | 0.7213 (6) | 0.0451 (11) | |
H1A | 0.4953 | 0.6062 | 0.7375 | 0.054* | |
C2 | 0.4682 (5) | 0.5276 (2) | 0.7621 (6) | 0.0472 (12) | |
H2A | 0.3940 | 0.5301 | 0.8069 | 0.057* | |
C3 | 0.5215 (6) | 0.4788 (2) | 0.7332 (6) | 0.0482 (12) | |
H3 | 0.4785 | 0.4477 | 0.7562 | 0.058* | |
C4 | 0.6884 (5) | 0.51959 (16) | 0.6398 (5) | 0.0328 (9) | |
C5 | 0.8671 (5) | 0.46637 (17) | 0.5550 (5) | 0.0350 (9) | |
H5A | 0.8979 | 0.4710 | 0.4701 | 0.042* | |
H5B | 0.7897 | 0.4386 | 0.5339 | 0.042* | |
C6 | 1.0024 (5) | 0.44711 (17) | 0.6770 (5) | 0.0350 (9) | |
C7 | 1.0368 (6) | 0.4667 (2) | 0.8155 (5) | 0.0443 (11) | |
H7 | 0.9729 | 0.4919 | 0.8365 | 0.053* | |
C8 | 1.1647 (6) | 0.4494 (2) | 0.9240 (6) | 0.0533 (13) | |
H8 | 1.1873 | 0.4635 | 1.0162 | 0.064* | |
C9 | 1.2577 (6) | 0.4113 (2) | 0.8933 (6) | 0.0499 (12) | |
H9 | 1.3435 | 0.3995 | 0.9653 | 0.060* | |
C10 | 1.2245 (5) | 0.39041 (18) | 0.7566 (5) | 0.0404 (10) | |
H10 | 1.2873 | 0.3641 | 0.7384 | 0.048* | |
C11 | 1.0981 (5) | 0.40809 (16) | 0.6445 (5) | 0.0347 (9) | |
C12 | 0.8956 (6) | 0.7416 (2) | 0.5634 (7) | 0.0660 (17) | |
H12A | 0.9608 | 0.7209 | 0.6360 | 0.079* | |
C13 | 0.9484 (7) | 0.7889 (2) | 0.5233 (9) | 0.078 (2) | |
H13 | 1.0475 | 0.8005 | 0.5669 | 0.094* | |
C14 | 0.8486 (6) | 0.8178 (2) | 0.4167 (7) | 0.0580 (14) | |
H14 | 0.8819 | 0.8498 | 0.3875 | 0.070* | |
C15 | 0.6627 (5) | 0.75617 (17) | 0.3970 (5) | 0.0392 (10) | |
C16 | 0.4023 (6) | 0.77407 (18) | 0.2440 (5) | 0.0446 (11) | |
H16A | 0.3197 | 0.7516 | 0.1869 | 0.054* | |
H16B | 0.4437 | 0.7930 | 0.1783 | 0.054* | |
C17 | 0.3390 (5) | 0.81517 (17) | 0.3238 (5) | 0.0355 (10) | |
C18 | 0.3894 (6) | 0.82048 (19) | 0.4713 (5) | 0.0447 (11) | |
H18 | 0.4671 | 0.7983 | 0.5255 | 0.054* | |
C19 | 0.3273 (6) | 0.8580 (2) | 0.5401 (6) | 0.0502 (12) | |
H19 | 0.3628 | 0.8609 | 0.6396 | 0.060* | |
C20 | 0.2126 (6) | 0.8911 (2) | 0.4609 (6) | 0.0503 (12) | |
H20 | 0.1701 | 0.9163 | 0.5069 | 0.060* | |
C21 | 0.1606 (6) | 0.88692 (19) | 0.3134 (6) | 0.0462 (12) | |
H21 | 0.0834 | 0.9095 | 0.2604 | 0.055* | |
C22 | 0.2225 (5) | 0.84915 (17) | 0.2430 (5) | 0.0361 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0552 (3) | 0.02896 (19) | 0.0589 (3) | 0.00169 (16) | 0.01237 (19) | 0.00829 (16) |
O1 | 0.0365 (17) | 0.0369 (16) | 0.0407 (19) | −0.0016 (14) | 0.0111 (15) | −0.0062 (13) |
O2 | 0.047 (2) | 0.0487 (19) | 0.0391 (19) | 0.0124 (16) | 0.0096 (16) | 0.0051 (15) |
O1W | 0.076 (3) | 0.048 (2) | 0.081 (3) | −0.020 (2) | 0.040 (3) | −0.005 (2) |
N1 | 0.036 (2) | 0.0258 (17) | 0.054 (2) | 0.0002 (15) | 0.0206 (19) | 0.0032 (16) |
N2 | 0.0352 (19) | 0.0296 (17) | 0.042 (2) | 0.0038 (16) | 0.0092 (17) | −0.0002 (15) |
N3 | 0.040 (2) | 0.0309 (18) | 0.055 (3) | 0.0011 (16) | 0.0223 (19) | 0.0027 (17) |
N4 | 0.036 (2) | 0.0319 (19) | 0.061 (3) | 0.0074 (17) | 0.011 (2) | 0.0106 (18) |
N5 | 0.054 (3) | 0.036 (2) | 0.055 (3) | 0.0006 (19) | 0.018 (2) | 0.0101 (18) |
N6 | 0.042 (2) | 0.0288 (19) | 0.058 (3) | 0.0006 (17) | 0.010 (2) | 0.0057 (18) |
C1 | 0.043 (3) | 0.040 (2) | 0.053 (3) | 0.009 (2) | 0.018 (2) | −0.003 (2) |
C2 | 0.035 (2) | 0.060 (3) | 0.050 (3) | 0.006 (2) | 0.019 (2) | 0.000 (2) |
C3 | 0.044 (3) | 0.043 (3) | 0.062 (3) | −0.002 (2) | 0.023 (3) | 0.007 (2) |
C4 | 0.029 (2) | 0.028 (2) | 0.039 (2) | −0.0002 (17) | 0.0069 (19) | 0.0012 (17) |
C5 | 0.030 (2) | 0.031 (2) | 0.046 (3) | 0.0026 (18) | 0.014 (2) | −0.0020 (18) |
C6 | 0.035 (2) | 0.032 (2) | 0.040 (2) | −0.0017 (18) | 0.016 (2) | 0.0007 (18) |
C7 | 0.047 (3) | 0.045 (3) | 0.044 (3) | 0.007 (2) | 0.020 (2) | 0.000 (2) |
C8 | 0.056 (3) | 0.062 (3) | 0.040 (3) | 0.004 (3) | 0.014 (3) | −0.001 (2) |
C9 | 0.044 (3) | 0.059 (3) | 0.045 (3) | 0.005 (2) | 0.011 (2) | 0.009 (2) |
C10 | 0.035 (2) | 0.038 (2) | 0.048 (3) | 0.007 (2) | 0.012 (2) | 0.003 (2) |
C11 | 0.036 (2) | 0.030 (2) | 0.041 (3) | −0.0045 (18) | 0.015 (2) | −0.0016 (18) |
C12 | 0.042 (3) | 0.052 (3) | 0.095 (5) | 0.010 (3) | 0.008 (3) | 0.022 (3) |
C13 | 0.040 (3) | 0.058 (4) | 0.131 (6) | −0.005 (3) | 0.017 (4) | 0.022 (4) |
C14 | 0.053 (3) | 0.044 (3) | 0.079 (4) | −0.004 (3) | 0.024 (3) | 0.010 (3) |
C15 | 0.042 (3) | 0.028 (2) | 0.050 (3) | 0.0072 (19) | 0.019 (2) | 0.0009 (19) |
C16 | 0.044 (3) | 0.033 (2) | 0.053 (3) | 0.005 (2) | 0.010 (2) | 0.002 (2) |
C17 | 0.036 (2) | 0.030 (2) | 0.039 (2) | −0.0042 (18) | 0.009 (2) | 0.0043 (18) |
C18 | 0.045 (3) | 0.041 (2) | 0.047 (3) | −0.004 (2) | 0.013 (2) | 0.004 (2) |
C19 | 0.060 (3) | 0.054 (3) | 0.036 (3) | −0.007 (3) | 0.013 (2) | −0.003 (2) |
C20 | 0.055 (3) | 0.051 (3) | 0.051 (3) | 0.002 (2) | 0.025 (3) | −0.007 (2) |
C21 | 0.045 (3) | 0.040 (3) | 0.057 (3) | 0.007 (2) | 0.021 (3) | 0.004 (2) |
C22 | 0.033 (2) | 0.035 (2) | 0.041 (2) | −0.0045 (18) | 0.013 (2) | 0.0049 (18) |
Ag1—N4 | 2.200 (4) | C5—H5A | 0.9700 |
Ag1—N2 | 2.204 (4) | C5—H5B | 0.9700 |
Ag1—O1i | 2.606 (3) | C6—C7 | 1.382 (6) |
Ag1—O1W | 2.963 (5) | C6—C11 | 1.419 (6) |
O1—C11 | 1.333 (5) | C7—C8 | 1.389 (7) |
O1—H1O | 0.840 (10) | C7—H7 | 0.9300 |
O2—C22 | 1.343 (5) | C8—C9 | 1.379 (7) |
O2—H2O | 0.839 (10) | C8—H8 | 0.9300 |
O1W—H11 | 0.842 (10) | C9—C10 | 1.379 (7) |
O1W—H12 | 0.840 (10) | C9—H9 | 0.9300 |
N1—C4 | 1.334 (5) | C10—C11 | 1.402 (6) |
N1—C5 | 1.454 (5) | C10—H10 | 0.9300 |
N1—H1 | 0.877 (10) | C12—C13 | 1.376 (8) |
N2—C1 | 1.343 (6) | C12—H12A | 0.9300 |
N2—C4 | 1.357 (5) | C13—C14 | 1.363 (8) |
N3—C3 | 1.331 (6) | C13—H13 | 0.9300 |
N3—C4 | 1.347 (5) | C14—H14 | 0.9300 |
N4—C12 | 1.336 (7) | C16—C17 | 1.514 (6) |
N4—C15 | 1.356 (6) | C16—H16A | 0.9700 |
N5—C14 | 1.328 (7) | C16—H16B | 0.9700 |
N5—C15 | 1.341 (6) | C17—C18 | 1.379 (6) |
N6—C15 | 1.340 (6) | C17—C22 | 1.403 (6) |
N6—C16 | 1.459 (6) | C18—C19 | 1.379 (7) |
N6—H6 | 0.877 (10) | C18—H18 | 0.9300 |
C1—C2 | 1.371 (7) | C19—C20 | 1.375 (7) |
C1—H1A | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.371 (7) | C20—C21 | 1.377 (7) |
C2—H2A | 0.9300 | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.393 (6) |
C5—C6 | 1.514 (6) | C21—H21 | 0.9300 |
N4—Ag1—N2 | 171.75 (14) | C9—C8—C7 | 119.2 (5) |
N4—Ag1—O1i | 86.43 (12) | C9—C8—H8 | 120.4 |
N2—Ag1—O1i | 100.50 (11) | C7—C8—H8 | 120.4 |
N4—Ag1—O1W | 97.51 (13) | C10—C9—C8 | 120.5 (5) |
N2—Ag1—O1W | 81.30 (12) | C10—C9—H9 | 119.7 |
O1i—Ag1—O1W | 131.60 (11) | C8—C9—H9 | 119.7 |
C11—O1—H1O | 124 (8) | C9—C10—C11 | 121.4 (4) |
C22—O2—H2O | 120 (9) | C9—C10—H10 | 119.3 |
Ag1—O1W—H11 | 142 (4) | C11—C10—H10 | 119.3 |
Ag1—O1W—H12 | 103 (4) | O1—C11—C10 | 121.3 (4) |
H11—O1W—H12 | 109 (2) | O1—C11—C6 | 120.8 (4) |
C4—N1—C5 | 124.2 (3) | C10—C11—C6 | 117.8 (4) |
C4—N1—H1 | 120 (3) | N4—C12—C13 | 122.1 (5) |
C5—N1—H1 | 115 (3) | N4—C12—H12A | 118.9 |
C1—N2—C4 | 116.5 (4) | C13—C12—H12A | 118.9 |
C1—N2—Ag1 | 118.3 (3) | C14—C13—C12 | 116.8 (5) |
C4—N2—Ag1 | 124.6 (3) | C14—C13—H13 | 121.6 |
C3—N3—C4 | 116.3 (4) | C12—C13—H13 | 121.6 |
C12—N4—C15 | 116.7 (4) | N5—C14—C13 | 123.3 (5) |
C12—N4—Ag1 | 115.6 (3) | N5—C14—H14 | 118.3 |
C15—N4—Ag1 | 127.5 (3) | C13—C14—H14 | 118.3 |
C14—N5—C15 | 116.5 (4) | N6—C15—N5 | 118.8 (4) |
C15—N6—C16 | 122.4 (4) | N6—C15—N4 | 116.8 (4) |
C15—N6—H6 | 120 (4) | N5—C15—N4 | 124.5 (4) |
C16—N6—H6 | 115 (4) | N6—C16—C17 | 114.6 (4) |
N2—C1—C2 | 122.7 (4) | N6—C16—H16A | 108.6 |
N2—C1—H1A | 118.7 | C17—C16—H16A | 108.6 |
C2—C1—H1A | 118.7 | N6—C16—H16B | 108.6 |
C3—C2—C1 | 116.3 (4) | C17—C16—H16B | 108.6 |
C3—C2—H2A | 121.8 | H16A—C16—H16B | 107.6 |
C1—C2—H2A | 121.8 | C18—C17—C22 | 118.8 (4) |
N3—C3—C2 | 123.7 (4) | C18—C17—C16 | 123.3 (4) |
N3—C3—H3 | 118.2 | C22—C17—C16 | 118.0 (4) |
C2—C3—H3 | 118.2 | C19—C18—C17 | 121.5 (5) |
N1—C4—N3 | 118.7 (4) | C19—C18—H18 | 119.3 |
N1—C4—N2 | 116.8 (4) | C17—C18—H18 | 119.3 |
N3—C4—N2 | 124.4 (4) | C20—C19—C18 | 119.7 (5) |
N1—C5—C6 | 114.5 (4) | C20—C19—H19 | 120.1 |
N1—C5—H5A | 108.6 | C18—C19—H19 | 120.1 |
C6—C5—H5A | 108.6 | C19—C20—C21 | 120.1 (5) |
N1—C5—H5B | 108.6 | C19—C20—H20 | 120.0 |
C6—C5—H5B | 108.6 | C21—C20—H20 | 120.0 |
H5A—C5—H5B | 107.6 | C20—C21—C22 | 120.6 (5) |
C7—C6—C11 | 119.6 (4) | C20—C21—H21 | 119.7 |
C7—C6—C5 | 122.9 (4) | C22—C21—H21 | 119.7 |
C11—C6—C5 | 117.4 (4) | O2—C22—C21 | 122.6 (4) |
C6—C7—C8 | 121.5 (4) | O2—C22—C17 | 118.0 (4) |
C6—C7—H7 | 119.3 | C21—C22—C17 | 119.3 (4) |
C8—C7—H7 | 119.3 | ||
O1i—Ag1—N2—C1 | 175.4 (3) | C7—C6—C11—O1 | −176.3 (4) |
O1W—Ag1—N2—C1 | −53.7 (3) | C5—C6—C11—O1 | 2.4 (6) |
O1i—Ag1—N2—C4 | −13.9 (4) | C7—C6—C11—C10 | 0.7 (6) |
O1W—Ag1—N2—C4 | 117.0 (4) | C5—C6—C11—C10 | 179.4 (4) |
O1i—Ag1—N4—C12 | −55.8 (4) | C15—N4—C12—C13 | −0.6 (9) |
O1W—Ag1—N4—C12 | 172.7 (4) | Ag1—N4—C12—C13 | 174.3 (5) |
O1i—Ag1—N4—C15 | 118.4 (4) | N4—C12—C13—C14 | 0.2 (11) |
O1W—Ag1—N4—C15 | −13.1 (4) | C15—N5—C14—C13 | −0.4 (9) |
C4—N2—C1—C2 | −1.1 (7) | C12—C13—C14—N5 | 0.4 (10) |
Ag1—N2—C1—C2 | 170.3 (4) | C16—N6—C15—N5 | −12.2 (7) |
N2—C1—C2—C3 | −1.2 (8) | C16—N6—C15—N4 | 167.5 (4) |
C4—N3—C3—C2 | −1.3 (8) | C14—N5—C15—N6 | 179.7 (5) |
C1—C2—C3—N3 | 2.6 (8) | C14—N5—C15—N4 | −0.1 (7) |
C5—N1—C4—N3 | 0.4 (7) | C12—N4—C15—N6 | −179.2 (5) |
C5—N1—C4—N2 | −179.7 (4) | Ag1—N4—C15—N6 | 6.6 (6) |
C3—N3—C4—N1 | 178.5 (4) | C12—N4—C15—N5 | 0.6 (7) |
C3—N3—C4—N2 | −1.4 (7) | Ag1—N4—C15—N5 | −173.6 (3) |
C1—N2—C4—N1 | −177.3 (4) | C15—N6—C16—C17 | −77.1 (6) |
Ag1—N2—C4—N1 | 11.8 (6) | N6—C16—C17—C18 | 1.2 (6) |
C1—N2—C4—N3 | 2.6 (7) | N6—C16—C17—C22 | −178.3 (4) |
Ag1—N2—C4—N3 | −168.3 (3) | C22—C17—C18—C19 | 0.5 (7) |
C4—N1—C5—C6 | −91.6 (5) | C16—C17—C18—C19 | −179.1 (4) |
N1—C5—C6—C7 | 16.3 (6) | C17—C18—C19—C20 | −0.1 (7) |
N1—C5—C6—C11 | −162.4 (4) | C18—C19—C20—C21 | −0.3 (8) |
C11—C6—C7—C8 | 0.8 (7) | C19—C20—C21—C22 | 0.4 (7) |
C5—C6—C7—C8 | −177.8 (4) | C20—C21—C22—O2 | −179.1 (4) |
C6—C7—C8—C9 | −1.2 (8) | C20—C21—C22—C17 | 0.0 (7) |
C7—C8—C9—C10 | 0.1 (8) | C18—C17—C22—O2 | 178.7 (4) |
C8—C9—C10—C11 | 1.5 (7) | C16—C17—C22—O2 | −1.7 (6) |
C9—C10—C11—O1 | 175.2 (4) | C18—C17—C22—C21 | −0.4 (6) |
C9—C10—C11—C6 | −1.9 (6) | C16—C17—C22—C21 | 179.2 (4) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O2ii | 0.84 (1) | 1.68 (3) | 2.504 (4) | 166 (12) |
O2—H2o···O1iii | 0.84 (1) | 1.68 (3) | 2.504 (4) | 166 (13) |
O1w—H11···O2iv | 0.84 (1) | 2.31 (6) | 2.927 (5) | 130 (6) |
O1w—H12···N3v | 0.84 (1) | 2.27 (2) | 3.085 (5) | 165 (6) |
N1—H1···O1i | 0.88 (1) | 1.99 (1) | 2.863 (5) | 176 (4) |
N6—H6···O1w | 0.88 (1) | 2.08 (2) | 2.943 (5) | 169 (5) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+3/2, z+1/2; (v) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C11H10N3O)2(C11H11N3O)2]·2H2O |
Mr | 1054.67 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.2992 (4), 24.808 (1), 9.8158 (5) |
β (°) | 108.453 (1) |
V (Å3) | 2148.02 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.98 |
Crystal size (mm) | 0.23 × 0.20 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.807, 0.852 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20943, 4910, 3230 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.133, 1.11 |
No. of reflections | 4910 |
No. of parameters | 307 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.27, −1.29 |
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—H1o···O2i | 0.84 (1) | 1.68 (3) | 2.504 (4) | 166 (12) |
O2—H2o···O1ii | 0.84 (1) | 1.68 (3) | 2.504 (4) | 166 (13) |
O1w—H11···O2iii | 0.84 (1) | 2.31 (6) | 2.927 (5) | 130 (6) |
O1w—H12···N3iv | 0.84 (1) | 2.27 (2) | 3.085 (5) | 165 (6) |
N1—H1···O1v | 0.88 (1) | 1.99 (1) | 2.863 (5) | 176 (4) |
N6—H6···O1w | 0.88 (1) | 2.08 (2) | 2.943 (5) | 169 (5) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+1, −z+1. |
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 (No. 12511z023, No. 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
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. (2011). Acta Cryst. E67, o3258. Web of Science CSD CrossRef IUCr Journals Google Scholar
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A recent study reports 2-[(pyrimidin-2-yl)aminomethyl]phenol, a reduced Schiff-base that possesses an acidic phenolic group (Xu et al., 2011). The reaction with silver nitrate yields dinuclear [Ag(C11H10N3O)(C11H11N3O)]2.2H2O (Scheme I, Fig. 1). The asymmetric unit has one Ag atom; however, the hydroxy H-atom is disordered over two positions in a 1:1 ratio. One half-occupancy H-atom is connected to O1 whereas the other half-occupancy atom is connected to O2. The AgI atom shows T-shaped coordination. Adjacent molecules are linked to the lattice water molecules to generate a O–H···O and N–H···O connected three-dimensional network (Table 1).