supplementary materials


xu5645 scheme

Acta Cryst. (2012). E68, m1543    [ doi:10.1107/S1600536812046119 ]

Tris{2-[(pyrimidin-2-yl-[kappa]N)aminomethyl]phenol}silver(I) nitrate

S. Gao and S. W. Ng

Abstract top

The AgI atom in the title compound, [Ag(C11H11N3O)3]NO3, shows a T-shaped coordination arising from bonding to the N atom of three N-heterocycles; the geometry is distorted towards square pyramidal owing to two weak Ag...Onitrate interactions [Ag...O = 2.691 (5) and 3.073 (5) Å]. The cation and anion are linked by O-H...N and N-H...O hydrogen bonds, generating a three-dimensional network.

Comment top

A recent study reports 2-[(pyrimidin-2-ylamino)methyl]phenol, a reduced Schiff-base that possesses an acidic phenolic group (Xu et al., 2011). The reaction with silver nitrate yields the salt, [Ag(C11H11N3O)3] NO3, in which the metal center shows T-shaped coordination arising from bonding to the N atom of three N-heterocycles (Scheme I, Fig. 1). The geometry is distorted towards a square pyramidal owing to two Ag···Onitrate interactions. The same O atom of the nitrate is involved, i.e., this atom engages in weak bridging to generate a dinuclear cation [Ag—O 2.691 (5), 3.073 (5) Å]. The cation and anion are linked by O–H···N and N–H···O hydrogen bonds to generate a three-dimensional network (Table 1).

Related literature top

For the structure of the 2-{[(pyrimidin-2-yl)amino]methyl}phenol ligand, see: Xu et al. (2011).

Experimental top

An acetonitrile solution (10 ml) of silver nitrate (1 mmol) was added to a methanol solution (5 ml) of 2-[(pyriamidin-2-ylamino)methyl]phenol (1 mmol) and aqueous ammonium 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.

Refinement top

Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino and hydroxy H atoms were located in a difference Fouier map, and were refined with distance restraints of N–H 0.88±0.01 and O–H 0.84±0.01 Å. Their temperature factors were refined tied by a factor of 1.5 times for O and 1.2 times for N.

The final difference Fourier map had a peak at 1.40 Å from N1 and a hole at 0.95 Å from Ag1.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Ag(C11H11N3O)3] NO3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The weak Ag···O interactions are shown as dashed lines.
Tris{2-[(pyrimidin-2-yl-κN)aminomethyl]phenol}silver(I) nitrate top
Crystal data top
[Ag(C11H11N3O)3]NO3Z = 2
Mr = 773.56F(000) = 792
Triclinic, P1Dx = 1.533 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5987 (4) ÅCell parameters from 8487 reflections
b = 13.7931 (7) Åθ = 3.0–27.5°
c = 16.1308 (10) ŵ = 0.66 mm1
α = 89.159 (2)°T = 293 K
β = 88.236 (2)°Prism, colorless
γ = 82.777 (1)°0.25 × 0.20 × 0.15 mm
V = 1676.35 (16) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
7609 independent reflections
Radiation source: fine-focus sealed tube3959 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ω scanθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.852, Tmax = 0.907k = 1716
16545 measured reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177 w = 1/[σ2(Fo2) + (0.0548P)2 + 4.1203P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
7609 reflectionsΔρmax = 1.17 e Å3
470 parametersΔρmin = 1.20 e Å3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0050 (9)
Crystal data top
[Ag(C11H11N3O)3]NO3γ = 82.777 (1)°
Mr = 773.56V = 1676.35 (16) Å3
Triclinic, P1Z = 2
a = 7.5987 (4) ÅMo Kα radiation
b = 13.7931 (7) ŵ = 0.66 mm1
c = 16.1308 (10) ÅT = 293 K
α = 89.159 (2)°0.25 × 0.20 × 0.15 mm
β = 88.236 (2)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
7609 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3959 reflections with I > 2σ(I)
Tmin = 0.852, Tmax = 0.907Rint = 0.065
16545 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177Δρmax = 1.17 e Å3
S = 1.05Δρmin = 1.20 e Å3
7609 reflectionsAbsolute structure: ?
470 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.69762 (7)0.56100 (4)0.41785 (3)0.0542 (2)
O10.3868 (7)0.3857 (4)0.0184 (3)0.0694 (14)
H1O0.357 (11)0.362 (6)0.026 (3)0.104*
O21.2106 (7)0.9698 (3)0.4381 (3)0.0667 (14)
H2O1.249 (11)1.023 (3)0.447 (5)0.100*
O31.1119 (7)0.6138 (4)0.0349 (3)0.0638 (13)
H3O1.132 (11)0.623 (6)0.0857 (13)0.096*
O40.3660 (6)0.5147 (4)0.4050 (3)0.0706 (14)
O50.1076 (7)0.5819 (5)0.4368 (4)0.102 (2)
O60.1982 (9)0.5706 (6)0.3104 (4)0.113 (2)
N10.8040 (6)0.4319 (3)0.3438 (3)0.0402 (11)
N20.8554 (6)0.3658 (4)0.2085 (3)0.0461 (13)
N30.5836 (6)0.4482 (4)0.2477 (3)0.0514 (14)
H3N0.505 (6)0.472 (4)0.286 (3)0.062*
N40.6185 (6)0.6924 (3)0.4963 (3)0.0395 (11)
N50.6519 (7)0.8562 (4)0.5321 (3)0.0479 (13)
N60.8682 (7)0.7597 (4)0.4565 (3)0.0494 (13)
H6N0.911 (8)0.702 (2)0.437 (4)0.059*
N70.6476 (7)0.6835 (4)0.2894 (3)0.0527 (14)
N80.6182 (7)0.6870 (4)0.1425 (3)0.0568 (15)
N90.8789 (7)0.6212 (4)0.2025 (3)0.0535 (14)
H9N0.934 (8)0.620 (5)0.250 (2)0.064*
N100.2226 (7)0.5580 (4)0.3840 (4)0.0500 (13)
C10.9638 (8)0.3903 (4)0.3636 (4)0.0480 (15)
H1A1.00240.39940.41670.058*
C21.0762 (9)0.3342 (5)0.3094 (5)0.0600 (18)
H2A1.18620.30330.32520.072*
C31.0165 (8)0.3265 (5)0.2311 (4)0.0535 (17)
H3A1.09130.29250.19180.064*
C40.7503 (7)0.4140 (4)0.2663 (3)0.0388 (14)
C50.5075 (8)0.4352 (5)0.1674 (4)0.0536 (17)
H5A0.59030.45180.12410.064*
H5B0.39970.48050.16280.064*
C60.4642 (7)0.3328 (5)0.1527 (4)0.0441 (15)
C70.4823 (8)0.2587 (5)0.2110 (4)0.0523 (17)
H70.52600.27070.26250.063*
C80.4378 (9)0.1679 (6)0.1953 (5)0.064 (2)
H80.45090.11950.23620.077*
C90.3732 (10)0.1475 (6)0.1188 (5)0.066 (2)
H90.34260.08570.10820.079*
C100.3548 (9)0.2194 (5)0.0590 (4)0.0579 (18)
H100.31200.20650.00750.069*
C110.4003 (8)0.3117 (5)0.0754 (4)0.0471 (15)
C120.4615 (8)0.7019 (5)0.5363 (4)0.0453 (15)
H120.39680.64890.53860.054*
C130.3924 (8)0.7870 (5)0.5742 (4)0.0512 (16)
H130.28180.79330.60130.061*
C140.4937 (8)0.8625 (5)0.5701 (4)0.0503 (16)
H140.44920.92110.59530.060*
C150.7105 (7)0.7705 (4)0.4960 (3)0.0387 (13)
C160.9941 (8)0.8302 (4)0.4533 (4)0.0486 (16)
H16A1.11230.79550.44490.058*
H16B0.99050.86230.50650.058*
C170.9631 (8)0.9068 (4)0.3869 (4)0.0439 (14)
C180.8294 (9)0.9114 (5)0.3308 (4)0.0556 (17)
H180.75340.86350.33250.067*
C190.8050 (11)0.9855 (6)0.2719 (4)0.067 (2)
H190.71270.98840.23500.080*
C200.9214 (12)1.0555 (5)0.2690 (5)0.071 (2)
H200.90861.10460.22870.085*
C211.0550 (11)1.0534 (5)0.3244 (5)0.068 (2)
H211.12921.10210.32310.082*
C221.0783 (9)0.9791 (5)0.3818 (4)0.0522 (16)
C230.4882 (10)0.7330 (6)0.2965 (5)0.065 (2)
H230.44100.74680.34950.078*
C240.3878 (10)0.7654 (7)0.2303 (5)0.080 (2)
H240.27930.80450.23670.096*
C250.4575 (10)0.7367 (7)0.1543 (5)0.074 (2)
H250.38900.75260.10810.088*
C260.7118 (9)0.6650 (5)0.2116 (4)0.0468 (15)
C270.9738 (9)0.6094 (5)0.1229 (4)0.0555 (17)
H27A0.90180.57870.08500.067*
H27B1.08260.56560.13030.067*
C281.0201 (7)0.7037 (5)0.0839 (4)0.0435 (14)
C290.9935 (8)0.7930 (5)0.1241 (4)0.0518 (16)
H290.94060.79670.17690.062*
C301.0442 (9)0.8758 (5)0.0871 (4)0.0636 (19)
H301.02890.93440.11580.076*
C311.1173 (9)0.8728 (5)0.0081 (5)0.0623 (19)
H311.14940.92930.01700.075*
C321.1429 (8)0.7854 (5)0.0336 (4)0.0534 (17)
H321.19450.78270.08670.064*
C331.0917 (8)0.7016 (5)0.0034 (4)0.0450 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0598 (3)0.0507 (3)0.0529 (4)0.0096 (2)0.0024 (2)0.0169 (2)
O10.088 (4)0.079 (4)0.044 (3)0.015 (3)0.024 (3)0.006 (3)
O20.065 (3)0.049 (3)0.090 (4)0.022 (2)0.015 (3)0.003 (3)
O30.089 (3)0.061 (3)0.040 (3)0.004 (3)0.009 (3)0.010 (2)
O40.043 (3)0.082 (4)0.086 (4)0.003 (3)0.008 (3)0.007 (3)
O50.075 (4)0.101 (5)0.124 (5)0.011 (3)0.042 (4)0.045 (4)
O60.121 (5)0.152 (6)0.073 (5)0.046 (5)0.036 (4)0.039 (4)
N10.040 (3)0.044 (3)0.036 (3)0.003 (2)0.000 (2)0.007 (2)
N20.044 (3)0.063 (3)0.031 (3)0.005 (3)0.006 (2)0.011 (2)
N30.038 (3)0.072 (4)0.042 (3)0.002 (3)0.002 (2)0.017 (3)
N40.051 (3)0.034 (3)0.034 (3)0.009 (2)0.002 (2)0.001 (2)
N50.056 (3)0.040 (3)0.047 (3)0.005 (2)0.003 (3)0.009 (2)
N60.051 (3)0.038 (3)0.060 (4)0.010 (3)0.012 (3)0.007 (3)
N70.054 (3)0.072 (4)0.035 (3)0.017 (3)0.006 (2)0.008 (3)
N80.052 (3)0.084 (4)0.036 (3)0.013 (3)0.008 (3)0.010 (3)
N90.052 (3)0.079 (4)0.029 (3)0.006 (3)0.001 (2)0.005 (3)
N100.047 (3)0.050 (3)0.054 (4)0.008 (3)0.002 (3)0.005 (3)
C10.056 (4)0.048 (4)0.041 (4)0.009 (3)0.003 (3)0.002 (3)
C20.046 (4)0.070 (5)0.062 (5)0.002 (3)0.004 (3)0.004 (4)
C30.044 (4)0.064 (4)0.051 (4)0.002 (3)0.004 (3)0.006 (3)
C40.041 (3)0.052 (4)0.024 (3)0.004 (3)0.001 (2)0.012 (3)
C50.045 (3)0.070 (5)0.046 (4)0.003 (3)0.011 (3)0.008 (3)
C60.034 (3)0.064 (4)0.033 (3)0.003 (3)0.002 (2)0.001 (3)
C70.046 (4)0.073 (5)0.038 (4)0.008 (3)0.008 (3)0.005 (3)
C80.058 (4)0.075 (5)0.059 (5)0.002 (4)0.007 (4)0.020 (4)
C90.070 (5)0.062 (5)0.067 (5)0.012 (4)0.001 (4)0.005 (4)
C100.059 (4)0.072 (5)0.045 (4)0.012 (4)0.008 (3)0.006 (4)
C110.047 (3)0.064 (4)0.029 (3)0.002 (3)0.008 (3)0.006 (3)
C120.051 (4)0.048 (4)0.037 (4)0.011 (3)0.007 (3)0.001 (3)
C130.050 (4)0.064 (4)0.038 (4)0.004 (3)0.008 (3)0.004 (3)
C140.051 (4)0.048 (4)0.050 (4)0.002 (3)0.004 (3)0.009 (3)
C150.043 (3)0.042 (3)0.031 (3)0.007 (3)0.004 (2)0.003 (3)
C160.043 (3)0.046 (4)0.058 (4)0.010 (3)0.002 (3)0.001 (3)
C170.044 (3)0.041 (3)0.046 (4)0.004 (3)0.005 (3)0.008 (3)
C180.066 (4)0.048 (4)0.054 (4)0.008 (3)0.004 (3)0.008 (3)
C190.086 (5)0.068 (5)0.043 (4)0.007 (4)0.012 (4)0.009 (4)
C200.116 (7)0.052 (4)0.041 (4)0.001 (5)0.012 (4)0.002 (3)
C210.094 (6)0.053 (4)0.058 (5)0.016 (4)0.001 (4)0.007 (4)
C220.056 (4)0.046 (4)0.055 (4)0.008 (3)0.006 (3)0.004 (3)
C230.056 (4)0.093 (6)0.049 (4)0.021 (4)0.005 (3)0.012 (4)
C240.054 (4)0.125 (8)0.057 (5)0.003 (5)0.007 (4)0.010 (5)
C250.059 (5)0.123 (7)0.041 (4)0.019 (5)0.014 (4)0.012 (4)
C260.056 (4)0.060 (4)0.028 (3)0.021 (3)0.003 (3)0.010 (3)
C270.061 (4)0.064 (4)0.041 (4)0.006 (3)0.001 (3)0.001 (3)
C280.040 (3)0.052 (4)0.038 (4)0.000 (3)0.000 (3)0.003 (3)
C290.048 (4)0.058 (4)0.048 (4)0.005 (3)0.003 (3)0.006 (3)
C300.072 (5)0.061 (5)0.055 (5)0.001 (4)0.015 (4)0.017 (4)
C310.068 (5)0.049 (4)0.068 (5)0.003 (4)0.005 (4)0.003 (4)
C320.054 (4)0.066 (5)0.037 (4)0.003 (3)0.005 (3)0.003 (3)
C330.046 (3)0.053 (4)0.033 (3)0.006 (3)0.001 (3)0.006 (3)
Geometric parameters (Å, º) top
Ag1—N12.212 (4)C7—C81.366 (10)
Ag1—N42.235 (4)C7—H70.9300
Ag1—N72.660 (5)C8—C91.388 (10)
Ag1—O42.691 (5)C8—H80.9300
O1—C111.359 (8)C9—C101.372 (10)
O1—H1O0.839 (10)C9—H90.9300
O2—C221.368 (8)C10—C111.391 (9)
O2—H2O0.839 (10)C10—H100.9300
O3—C331.357 (7)C12—C131.369 (8)
O3—H3O0.840 (10)C12—H120.9300
O4—N101.229 (7)C13—C141.370 (9)
O5—N101.219 (7)C13—H130.9300
O6—N101.215 (7)C14—H140.9300
N1—C11.322 (7)C16—C171.496 (9)
N1—C41.362 (7)C16—H16A0.9700
N2—C31.333 (8)C16—H16B0.9700
N2—C41.337 (7)C17—C181.377 (9)
N3—C41.337 (7)C17—C221.406 (8)
N3—C51.457 (8)C18—C191.385 (10)
N3—H3N0.880 (10)C18—H180.9300
N4—C121.332 (7)C19—C201.388 (10)
N4—C151.355 (7)C19—H190.9300
N5—C141.326 (8)C20—C211.371 (11)
N5—C151.345 (7)C20—H200.9300
N6—C151.332 (7)C21—C221.369 (10)
N6—C161.447 (7)C21—H210.9300
N6—H6N0.879 (10)C23—C241.367 (10)
N7—C231.316 (9)C23—H230.9300
N7—C261.349 (8)C24—C251.365 (10)
N8—C251.332 (9)C24—H240.9300
N8—C261.351 (8)C25—H250.9300
N9—C261.341 (8)C27—C281.514 (9)
N9—C271.454 (8)C27—H27A0.9700
N9—H9N0.880 (10)C27—H27B0.9700
C1—C21.378 (9)C28—C291.389 (8)
C1—H1A0.9300C28—C331.391 (8)
C2—C31.366 (9)C29—C301.373 (9)
C2—H2A0.9300C29—H290.9300
C3—H3A0.9300C30—C311.373 (10)
C5—C61.513 (9)C30—H300.9300
C5—H5A0.9700C31—C321.378 (9)
C5—H5B0.9700C31—H310.9300
C6—C71.376 (9)C32—C331.388 (9)
C6—C111.400 (8)C32—H320.9300
N1—Ag1—N4174.16 (17)N4—C12—H12119.0
N1—Ag1—N795.84 (18)C13—C12—H12119.0
N4—Ag1—N785.61 (17)C12—C13—C14116.9 (6)
N1—Ag1—O490.50 (16)C12—C13—H13121.6
N4—Ag1—O495.16 (17)C14—C13—H13121.6
N7—Ag1—O490.16 (16)N5—C14—C13123.3 (6)
C11—O1—H1O107 (6)N5—C14—H14118.3
C22—O2—H2O112 (6)C13—C14—H14118.3
C33—O3—H3O109 (6)N6—C15—N5119.3 (5)
N10—O4—Ag1135.7 (4)N6—C15—N4116.5 (5)
C1—N1—C4116.4 (5)N5—C15—N4124.2 (5)
C1—N1—Ag1115.5 (4)N6—C16—C17114.9 (5)
C4—N1—Ag1124.1 (4)N6—C16—H16A108.6
C3—N2—C4117.4 (5)C17—C16—H16A108.6
C4—N3—C5123.6 (5)N6—C16—H16B108.6
C4—N3—H3N122 (4)C17—C16—H16B108.6
C5—N3—H3N113 (4)H16A—C16—H16B107.5
C12—N4—C15117.1 (5)C18—C17—C22118.0 (6)
C12—N4—Ag1119.2 (4)C18—C17—C16124.4 (5)
C15—N4—Ag1123.0 (4)C22—C17—C16117.7 (6)
C14—N5—C15116.4 (5)C17—C18—C19121.7 (6)
C15—N6—C16126.0 (5)C17—C18—H18119.2
C15—N6—H6N119 (4)C19—C18—H18119.2
C16—N6—H6N114 (4)C18—C19—C20118.6 (7)
C23—N7—C26116.5 (6)C18—C19—H19120.7
C23—N7—Ag1109.1 (4)C20—C19—H19120.7
C26—N7—Ag1125.0 (5)C21—C20—C19121.1 (7)
C25—N8—C26115.9 (6)C21—C20—H20119.4
C26—N9—C27123.6 (5)C19—C20—H20119.4
C26—N9—H9N110 (4)C22—C21—C20119.6 (7)
C27—N9—H9N122 (4)C22—C21—H21120.2
O6—N10—O5122.5 (7)C20—C21—H21120.2
O6—N10—O4118.0 (6)O2—C22—C21123.5 (6)
O5—N10—O4119.4 (7)O2—C22—C17115.4 (6)
N1—C1—C2123.4 (6)C21—C22—C17121.0 (7)
N1—C1—H1A118.3N7—C23—C24123.8 (7)
C2—C1—H1A118.3N7—C23—H23118.1
C3—C2—C1116.0 (6)C24—C23—H23118.1
C3—C2—H2A122.0C25—C24—C23115.5 (8)
C1—C2—H2A122.0C25—C24—H24122.2
N2—C3—C2122.8 (6)C23—C24—H24122.2
N2—C3—H3A118.6N8—C25—C24123.7 (7)
C2—C3—H3A118.6N8—C25—H25118.2
N3—C4—N2119.0 (5)C24—C25—H25118.2
N3—C4—N1117.3 (5)N9—C26—N7117.7 (6)
N2—C4—N1123.6 (5)N9—C26—N8118.1 (6)
N3—C5—C6114.3 (6)N7—C26—N8124.2 (6)
N3—C5—H5A108.7N9—C27—C28114.5 (5)
C6—C5—H5A108.7N9—C27—H27A108.6
N3—C5—H5B108.7C28—C27—H27A108.6
C6—C5—H5B108.7N9—C27—H27B108.6
H5A—C5—H5B107.6C28—C27—H27B108.6
C7—C6—C11117.5 (6)H27A—C27—H27B107.6
C7—C6—C5124.1 (5)C29—C28—C33118.0 (6)
C11—C6—C5118.4 (6)C29—C28—C27123.3 (6)
C8—C7—C6121.9 (6)C33—C28—C27118.6 (5)
C8—C7—H7119.0C30—C29—C28121.0 (6)
C6—C7—H7119.0C30—C29—H29119.5
C7—C8—C9120.4 (7)C28—C29—H29119.5
C7—C8—H8119.8C29—C30—C31120.6 (6)
C9—C8—H8119.8C29—C30—H30119.7
C10—C9—C8119.2 (7)C31—C30—H30119.7
C10—C9—H9120.4C30—C31—C32119.6 (7)
C8—C9—H9120.4C30—C31—H31120.2
C9—C10—C11120.0 (6)C32—C31—H31120.2
C9—C10—H10120.0C31—C32—C33120.1 (6)
C11—C10—H10120.0C31—C32—H32119.9
O1—C11—C10122.8 (6)C33—C32—H32119.9
O1—C11—C6116.3 (6)O3—C33—C32122.8 (5)
C10—C11—C6120.9 (6)O3—C33—C28116.6 (6)
N4—C12—C13122.1 (6)C32—C33—C28120.6 (6)
N1—Ag1—O4—N10128.7 (6)C12—C13—C14—N50.1 (10)
N4—Ag1—O4—N1052.8 (6)C16—N6—C15—N55.0 (10)
N7—Ag1—O4—N1032.9 (6)C16—N6—C15—N4175.2 (6)
N7—Ag1—N1—C1122.7 (4)C14—N5—C15—N6179.8 (6)
O4—Ag1—N1—C1147.1 (4)C14—N5—C15—N40.1 (9)
N7—Ag1—N1—C434.0 (5)C12—N4—C15—N6179.3 (5)
O4—Ag1—N1—C456.2 (4)Ag1—N4—C15—N610.6 (7)
N7—Ag1—N4—C12108.4 (4)C12—N4—C15—N51.0 (8)
O4—Ag1—N4—C1218.7 (5)Ag1—N4—C15—N5169.1 (4)
N7—Ag1—N4—C1561.5 (4)C15—N6—C16—C1784.9 (8)
O4—Ag1—N4—C15151.3 (4)N6—C16—C17—C181.4 (9)
N1—Ag1—N7—C23132.8 (5)N6—C16—C17—C22178.5 (5)
N4—Ag1—N7—C2352.8 (5)C22—C17—C18—C191.3 (9)
O4—Ag1—N7—C2342.3 (5)C16—C17—C18—C19178.5 (6)
N1—Ag1—N7—C2612.2 (5)C17—C18—C19—C201.2 (10)
N4—Ag1—N7—C26162.2 (5)C18—C19—C20—C211.8 (11)
O4—Ag1—N7—C26102.7 (5)C19—C20—C21—C222.4 (11)
Ag1—O4—N10—O677.5 (8)C20—C21—C22—O2178.3 (7)
Ag1—O4—N10—O5106.3 (7)C20—C21—C22—C172.5 (11)
C4—N1—C1—C22.2 (9)C18—C17—C22—O2178.8 (6)
Ag1—N1—C1—C2156.3 (5)C16—C17—C22—O21.3 (8)
N1—C1—C2—C32.7 (10)C18—C17—C22—C212.0 (9)
C4—N2—C3—C20.2 (10)C16—C17—C22—C21177.9 (6)
C1—C2—C3—N23.7 (10)C26—N7—C23—C240.0 (11)
C5—N3—C4—N20.7 (9)Ag1—N7—C23—C24148.3 (7)
C5—N3—C4—N1179.8 (6)N7—C23—C24—C255.0 (12)
C3—N2—C4—N3175.2 (6)C26—N8—C25—C240.5 (12)
C3—N2—C4—N15.8 (9)C23—C24—C25—N85.2 (13)
C1—N1—C4—N3174.3 (5)C27—N9—C26—N7170.8 (6)
Ag1—N1—C4—N329.2 (7)C27—N9—C26—N89.7 (9)
C1—N1—C4—N26.7 (9)C23—N7—C26—N9175.1 (6)
Ag1—N1—C4—N2149.8 (5)Ag1—N7—C26—N942.1 (7)
C4—N3—C5—C674.2 (8)C23—N7—C26—N85.5 (9)
N3—C5—C6—C74.3 (9)Ag1—N7—C26—N8137.3 (5)
N3—C5—C6—C11176.3 (5)C25—N8—C26—N9175.4 (6)
C11—C6—C7—C80.9 (9)C25—N8—C26—N75.2 (10)
C5—C6—C7—C8178.6 (6)C26—N9—C27—C2868.8 (8)
C6—C7—C8—C90.4 (10)N9—C27—C28—C297.2 (9)
C7—C8—C9—C100.2 (11)N9—C27—C28—C33172.4 (5)
C8—C9—C10—C110.2 (11)C33—C28—C29—C303.0 (9)
C9—C10—C11—O1179.4 (6)C27—C28—C29—C30177.4 (6)
C9—C10—C11—C60.4 (10)C28—C29—C30—C312.1 (11)
C7—C6—C11—O1178.9 (6)C29—C30—C31—C321.2 (11)
C5—C6—C11—O11.7 (8)C30—C31—C32—C331.3 (10)
C7—C6—C11—C100.9 (9)C31—C32—C33—O3179.3 (6)
C5—C6—C11—C10178.6 (6)C31—C32—C33—C282.3 (10)
C15—N4—C12—C131.4 (9)C29—C28—C33—O3178.4 (5)
Ag1—N4—C12—C13169.1 (5)C27—C28—C33—O31.2 (8)
N4—C12—C13—C140.9 (10)C29—C28—C33—C323.1 (9)
C15—N5—C14—C130.5 (10)C27—C28—C33—C32177.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N8i0.84 (1)2.00 (3)2.800 (7)158 (9)
O2—H2o···N5ii0.84 (1)1.95 (1)2.788 (6)177 (9)
O3—H3o···N2iii0.84 (1)1.99 (2)2.818 (6)171 (8)
N3—H3n···O40.88 (1)2.22 (2)3.073 (7)164 (6)
N6—H6n···O5iv0.88 (1)2.09 (4)2.879 (8)149 (6)
N9—H9n···O6iv0.88 (1)2.28 (4)3.033 (8)143 (6)
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+2, z+1; (iii) x+2, y+1, z; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N8i0.84 (1)2.00 (3)2.800 (7)158 (9)
O2—H2o···N5ii0.84 (1)1.95 (1)2.788 (6)177 (9)
O3—H3o···N2iii0.84 (1)1.99 (2)2.818 (6)171 (8)
N3—H3n···O40.88 (1)2.22 (2)3.073 (7)164 (6)
N6—H6n···O5iv0.88 (1)2.09 (4)2.879 (8)149 (6)
N9—H9n···O6iv0.88 (1)2.28 (4)3.033 (8)143 (6)
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+2, z+1; (iii) x+2, y+1, z; (iv) x+1, y, z.
Acknowledgements top

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
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Xu, J., Gao, S. & Ng, S. W. (2011). Acta Cryst. E67, o3258.