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

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812046119

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1543

doi:10.1107/S1600536812046119

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

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^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

(Received 31 October 2012; accepted 8 November 2012; online 28 November 2012)

The Ag^I 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⋯O_nitrate 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.

Related literature

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

Experimental

Crystal data

[Ag(C₁₁H₁₁N₃O)₃]NO₃
M_r = 773.56
Triclinic, $[P \overline 1]$
a = 7.5987 (4) Å
b = 13.7931 (7) Å
c = 16.1308 (10) Å
α = 89.159 (2)°
β = 88.236 (2)°
γ = 82.777 (1)°
V = 1676.35 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.852, T_max = 0.907
16545 measured reflections
7609 independent reflections
3959 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.177
S = 1.05
7609 reflections
470 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.17 e Å⁻³
Δρ_min = −1.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N8ⁱ	0.84 (1)	2.00 (3)	2.800 (7)	158 (9)
O2—H2o⋯N5ⁱⁱ	0.84 (1)	1.95 (1)	2.788 (6)	177 (9)
O3—H3o⋯N2ⁱⁱⁱ	0.84 (1)	1.99 (2)	2.818 (6)	171 (8)
N3—H3n⋯O4	0.88 (1)	2.22 (2)	3.073 (7)	164 (6)
N6—H6n⋯O5^iv	0.88 (1)	2.09 (4)	2.879 (8)	149 (6)
N9—H9n⋯O6^iv	0.88 (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.

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812046119/xu5645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046119/xu5645Isup2.hkl

checkCIF report

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···O_nitrate 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.

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

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]NO₃	Z = 2
M_r = 773.56	F(000) = 792
Triclinic, P1	D_x = 1.533 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5987 (4) Å	Cell parameters from 8487 reflections
b = 13.7931 (7) Å	θ = 3.0–27.5°
c = 16.1308 (10) Å	µ = 0.66 mm⁻¹
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 tube	3959 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.852, T_max = 0.907	k = −17→16
16545 measured reflections	l = −20→20

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.177	w = 1/[σ²(F_o²) + (0.0548P)² + 4.1203P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
7609 reflections	Δρ_max = 1.17 e Å⁻³
470 parameters	Δρ_min = −1.20 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (9)

Crystal data top

[Ag(C₁₁H₁₁N₃O)₃]NO₃	γ = 82.777 (1)°
M_r = 773.56	V = 1676.35 (16) Å³
Triclinic, P1	Z = 2
a = 7.5987 (4) Å	Mo Kα radiation
b = 13.7931 (7) Å	µ = 0.66 mm⁻¹
c = 16.1308 (10) Å	T = 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)
T_min = 0.852, T_max = 0.907	R_int = 0.065
16545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	6 restraints
wR(F²) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.17 e Å⁻³
7609 reflections	Δρ_min = −1.20 e Å⁻³
470 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.69762 (7)	0.56100 (4)	0.41785 (3)	0.0542 (2)
O1	0.3868 (7)	0.3857 (4)	0.0184 (3)	0.0694 (14)
H1O	0.357 (11)	0.362 (6)	−0.026 (3)	0.104*
O2	1.2106 (7)	0.9698 (3)	0.4381 (3)	0.0667 (14)
H2O	1.249 (11)	1.023 (3)	0.447 (5)	0.100*
O3	1.1119 (7)	0.6138 (4)	−0.0349 (3)	0.0638 (13)
H3O	1.132 (11)	0.623 (6)	−0.0857 (13)	0.096*
O4	0.3660 (6)	0.5147 (4)	0.4050 (3)	0.0706 (14)
O5	0.1076 (7)	0.5819 (5)	0.4368 (4)	0.102 (2)
O6	0.1982 (9)	0.5706 (6)	0.3104 (4)	0.113 (2)
N1	0.8040 (6)	0.4319 (3)	0.3438 (3)	0.0402 (11)
N2	0.8554 (6)	0.3658 (4)	0.2085 (3)	0.0461 (13)
N3	0.5836 (6)	0.4482 (4)	0.2477 (3)	0.0514 (14)
H3N	0.505 (6)	0.472 (4)	0.286 (3)	0.062*
N4	0.6185 (6)	0.6924 (3)	0.4963 (3)	0.0395 (11)
N5	0.6519 (7)	0.8562 (4)	0.5321 (3)	0.0479 (13)
N6	0.8682 (7)	0.7597 (4)	0.4565 (3)	0.0494 (13)
H6N	0.911 (8)	0.702 (2)	0.437 (4)	0.059*
N7	0.6476 (7)	0.6835 (4)	0.2894 (3)	0.0527 (14)
N8	0.6182 (7)	0.6870 (4)	0.1425 (3)	0.0568 (15)
N9	0.8789 (7)	0.6212 (4)	0.2025 (3)	0.0535 (14)
H9N	0.934 (8)	0.620 (5)	0.250 (2)	0.064*
N10	0.2226 (7)	0.5580 (4)	0.3840 (4)	0.0500 (13)
C1	0.9638 (8)	0.3903 (4)	0.3636 (4)	0.0480 (15)
H1A	1.0024	0.3994	0.4167	0.058*
C2	1.0762 (9)	0.3342 (5)	0.3094 (5)	0.0600 (18)
H2A	1.1862	0.3033	0.3252	0.072*
C3	1.0165 (8)	0.3265 (5)	0.2311 (4)	0.0535 (17)
H3A	1.0913	0.2925	0.1918	0.064*
C4	0.7503 (7)	0.4140 (4)	0.2663 (3)	0.0388 (14)
C5	0.5075 (8)	0.4352 (5)	0.1674 (4)	0.0536 (17)
H5A	0.5903	0.4518	0.1241	0.064*
H5B	0.3997	0.4805	0.1628	0.064*
C6	0.4642 (7)	0.3328 (5)	0.1527 (4)	0.0441 (15)
C7	0.4823 (8)	0.2587 (5)	0.2110 (4)	0.0523 (17)
H7	0.5260	0.2707	0.2625	0.063*
C8	0.4378 (9)	0.1679 (6)	0.1953 (5)	0.064 (2)
H8	0.4509	0.1195	0.2362	0.077*
C9	0.3732 (10)	0.1475 (6)	0.1188 (5)	0.066 (2)
H9	0.3426	0.0857	0.1082	0.079*
C10	0.3548 (9)	0.2194 (5)	0.0590 (4)	0.0579 (18)
H10	0.3120	0.2065	0.0075	0.069*
C11	0.4003 (8)	0.3117 (5)	0.0754 (4)	0.0471 (15)
C12	0.4615 (8)	0.7019 (5)	0.5363 (4)	0.0453 (15)
H12	0.3968	0.6489	0.5386	0.054*
C13	0.3924 (8)	0.7870 (5)	0.5742 (4)	0.0512 (16)
H13	0.2818	0.7933	0.6013	0.061*
C14	0.4937 (8)	0.8625 (5)	0.5701 (4)	0.0503 (16)
H14	0.4492	0.9211	0.5953	0.060*
C15	0.7105 (7)	0.7705 (4)	0.4960 (3)	0.0387 (13)
C16	0.9941 (8)	0.8302 (4)	0.4533 (4)	0.0486 (16)
H16A	1.1123	0.7955	0.4449	0.058*
H16B	0.9905	0.8623	0.5065	0.058*
C17	0.9631 (8)	0.9068 (4)	0.3869 (4)	0.0439 (14)
C18	0.8294 (9)	0.9114 (5)	0.3308 (4)	0.0556 (17)
H18	0.7534	0.8635	0.3325	0.067*
C19	0.8050 (11)	0.9855 (6)	0.2719 (4)	0.067 (2)
H19	0.7127	0.9884	0.2350	0.080*
C20	0.9214 (12)	1.0555 (5)	0.2690 (5)	0.071 (2)
H20	0.9086	1.1046	0.2287	0.085*
C21	1.0550 (11)	1.0534 (5)	0.3244 (5)	0.068 (2)
H21	1.1292	1.1021	0.3231	0.082*
C22	1.0783 (9)	0.9791 (5)	0.3818 (4)	0.0522 (16)
C23	0.4882 (10)	0.7330 (6)	0.2965 (5)	0.065 (2)
H23	0.4410	0.7468	0.3495	0.078*
C24	0.3878 (10)	0.7654 (7)	0.2303 (5)	0.080 (2)
H24	0.2793	0.8045	0.2367	0.096*
C25	0.4575 (10)	0.7367 (7)	0.1543 (5)	0.074 (2)
H25	0.3890	0.7526	0.1081	0.088*
C26	0.7118 (9)	0.6650 (5)	0.2116 (4)	0.0468 (15)
C27	0.9738 (9)	0.6094 (5)	0.1229 (4)	0.0555 (17)
H27A	0.9018	0.5787	0.0850	0.067*
H27B	1.0826	0.5656	0.1303	0.067*
C28	1.0201 (7)	0.7037 (5)	0.0839 (4)	0.0435 (14)
C29	0.9935 (8)	0.7930 (5)	0.1241 (4)	0.0518 (16)
H29	0.9406	0.7967	0.1769	0.062*
C30	1.0442 (9)	0.8758 (5)	0.0871 (4)	0.0636 (19)
H30	1.0289	0.9344	0.1158	0.076*
C31	1.1173 (9)	0.8728 (5)	0.0081 (5)	0.0623 (19)
H31	1.1494	0.9293	−0.0170	0.075*
C32	1.1429 (8)	0.7854 (5)	−0.0336 (4)	0.0534 (17)
H32	1.1945	0.7827	−0.0867	0.064*
C33	1.0917 (8)	0.7016 (5)	0.0034 (4)	0.0450 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0598 (3)	0.0507 (3)	0.0529 (4)	−0.0096 (2)	0.0024 (2)	−0.0169 (2)
O1	0.088 (4)	0.079 (4)	0.044 (3)	−0.015 (3)	−0.024 (3)	0.006 (3)
O2	0.065 (3)	0.049 (3)	0.090 (4)	−0.022 (2)	−0.015 (3)	0.003 (3)
O3	0.089 (3)	0.061 (3)	0.040 (3)	−0.004 (3)	0.009 (3)	−0.010 (2)
O4	0.043 (3)	0.082 (4)	0.086 (4)	−0.003 (3)	−0.008 (3)	0.007 (3)
O5	0.075 (4)	0.101 (5)	0.124 (5)	0.011 (3)	0.042 (4)	−0.045 (4)
O6	0.121 (5)	0.152 (6)	0.073 (5)	−0.046 (5)	−0.036 (4)	0.039 (4)
N1	0.040 (3)	0.044 (3)	0.036 (3)	−0.003 (2)	0.000 (2)	−0.007 (2)
N2	0.044 (3)	0.063 (3)	0.031 (3)	−0.005 (3)	0.006 (2)	−0.011 (2)
N3	0.038 (3)	0.072 (4)	0.042 (3)	0.002 (3)	0.002 (2)	−0.017 (3)
N4	0.051 (3)	0.034 (3)	0.034 (3)	−0.009 (2)	0.002 (2)	−0.001 (2)
N5	0.056 (3)	0.040 (3)	0.047 (3)	−0.005 (2)	0.003 (3)	−0.009 (2)
N6	0.051 (3)	0.038 (3)	0.060 (4)	−0.010 (3)	0.012 (3)	−0.007 (3)
N7	0.054 (3)	0.072 (4)	0.035 (3)	−0.017 (3)	−0.006 (2)	0.008 (3)
N8	0.052 (3)	0.084 (4)	0.036 (3)	−0.013 (3)	−0.008 (3)	0.010 (3)
N9	0.052 (3)	0.079 (4)	0.029 (3)	−0.006 (3)	0.001 (2)	0.005 (3)
N10	0.047 (3)	0.050 (3)	0.054 (4)	−0.008 (3)	0.002 (3)	−0.005 (3)
C1	0.056 (4)	0.048 (4)	0.041 (4)	−0.009 (3)	−0.003 (3)	−0.002 (3)
C2	0.046 (4)	0.070 (5)	0.062 (5)	0.002 (3)	−0.004 (3)	−0.004 (4)
C3	0.044 (4)	0.064 (4)	0.051 (4)	−0.002 (3)	0.004 (3)	−0.006 (3)
C4	0.041 (3)	0.052 (4)	0.024 (3)	−0.004 (3)	0.001 (2)	−0.012 (3)
C5	0.045 (3)	0.070 (5)	0.046 (4)	−0.003 (3)	−0.011 (3)	−0.008 (3)
C6	0.034 (3)	0.064 (4)	0.033 (3)	−0.003 (3)	−0.002 (2)	−0.001 (3)
C7	0.046 (4)	0.073 (5)	0.038 (4)	−0.008 (3)	−0.008 (3)	−0.005 (3)
C8	0.058 (4)	0.075 (5)	0.059 (5)	−0.002 (4)	−0.007 (4)	0.020 (4)
C9	0.070 (5)	0.062 (5)	0.067 (5)	−0.012 (4)	0.001 (4)	−0.005 (4)
C10	0.059 (4)	0.072 (5)	0.045 (4)	−0.012 (4)	−0.008 (3)	−0.006 (4)
C11	0.047 (3)	0.064 (4)	0.029 (3)	−0.002 (3)	−0.008 (3)	0.006 (3)
C12	0.051 (4)	0.048 (4)	0.037 (4)	−0.011 (3)	0.007 (3)	−0.001 (3)
C13	0.050 (4)	0.064 (4)	0.038 (4)	−0.004 (3)	0.008 (3)	−0.004 (3)
C14	0.051 (4)	0.048 (4)	0.050 (4)	0.002 (3)	0.004 (3)	−0.009 (3)
C15	0.043 (3)	0.042 (3)	0.031 (3)	−0.007 (3)	−0.004 (2)	0.003 (3)
C16	0.043 (3)	0.046 (4)	0.058 (4)	−0.010 (3)	0.002 (3)	0.001 (3)
C17	0.044 (3)	0.041 (3)	0.046 (4)	−0.004 (3)	0.005 (3)	−0.008 (3)
C18	0.066 (4)	0.048 (4)	0.054 (4)	−0.008 (3)	−0.004 (3)	−0.008 (3)
C19	0.086 (5)	0.068 (5)	0.043 (4)	0.007 (4)	−0.012 (4)	−0.009 (4)
C20	0.116 (7)	0.052 (4)	0.041 (4)	−0.001 (5)	0.012 (4)	−0.002 (3)
C21	0.094 (6)	0.053 (4)	0.058 (5)	−0.016 (4)	0.001 (4)	0.007 (4)
C22	0.056 (4)	0.046 (4)	0.055 (4)	−0.008 (3)	0.006 (3)	−0.004 (3)
C23	0.056 (4)	0.093 (6)	0.049 (4)	−0.021 (4)	−0.005 (3)	0.012 (4)
C24	0.054 (4)	0.125 (8)	0.057 (5)	0.003 (5)	−0.007 (4)	0.010 (5)
C25	0.059 (5)	0.123 (7)	0.041 (4)	−0.019 (5)	−0.014 (4)	0.012 (4)
C26	0.056 (4)	0.060 (4)	0.028 (3)	−0.021 (3)	−0.003 (3)	0.010 (3)
C27	0.061 (4)	0.064 (4)	0.041 (4)	−0.006 (3)	−0.001 (3)	0.001 (3)
C28	0.040 (3)	0.052 (4)	0.038 (4)	0.000 (3)	0.000 (3)	−0.003 (3)
C29	0.048 (4)	0.058 (4)	0.048 (4)	−0.005 (3)	0.003 (3)	−0.006 (3)
C30	0.072 (5)	0.061 (5)	0.055 (5)	−0.001 (4)	0.015 (4)	−0.017 (4)
C31	0.068 (5)	0.049 (4)	0.068 (5)	−0.003 (4)	0.005 (4)	0.003 (4)
C32	0.054 (4)	0.066 (5)	0.037 (4)	0.003 (3)	0.005 (3)	0.003 (3)
C33	0.046 (3)	0.053 (4)	0.033 (3)	0.006 (3)	0.001 (3)	−0.006 (3)

Geometric parameters (Å, º) top

Ag1—N1	2.212 (4)	C7—C8	1.366 (10)
Ag1—N4	2.235 (4)	C7—H7	0.9300
Ag1—N7	2.660 (5)	C8—C9	1.388 (10)
Ag1—O4	2.691 (5)	C8—H8	0.9300
O1—C11	1.359 (8)	C9—C10	1.372 (10)
O1—H1O	0.839 (10)	C9—H9	0.9300
O2—C22	1.368 (8)	C10—C11	1.391 (9)
O2—H2O	0.839 (10)	C10—H10	0.9300
O3—C33	1.357 (7)	C12—C13	1.369 (8)
O3—H3O	0.840 (10)	C12—H12	0.9300
O4—N10	1.229 (7)	C13—C14	1.370 (9)
O5—N10	1.219 (7)	C13—H13	0.9300
O6—N10	1.215 (7)	C14—H14	0.9300
N1—C1	1.322 (7)	C16—C17	1.496 (9)
N1—C4	1.362 (7)	C16—H16A	0.9700
N2—C3	1.333 (8)	C16—H16B	0.9700
N2—C4	1.337 (7)	C17—C18	1.377 (9)
N3—C4	1.337 (7)	C17—C22	1.406 (8)
N3—C5	1.457 (8)	C18—C19	1.385 (10)
N3—H3N	0.880 (10)	C18—H18	0.9300
N4—C12	1.332 (7)	C19—C20	1.388 (10)
N4—C15	1.355 (7)	C19—H19	0.9300
N5—C14	1.326 (8)	C20—C21	1.371 (11)
N5—C15	1.345 (7)	C20—H20	0.9300
N6—C15	1.332 (7)	C21—C22	1.369 (10)
N6—C16	1.447 (7)	C21—H21	0.9300
N6—H6N	0.879 (10)	C23—C24	1.367 (10)
N7—C23	1.316 (9)	C23—H23	0.9300
N7—C26	1.349 (8)	C24—C25	1.365 (10)
N8—C25	1.332 (9)	C24—H24	0.9300
N8—C26	1.351 (8)	C25—H25	0.9300
N9—C26	1.341 (8)	C27—C28	1.514 (9)
N9—C27	1.454 (8)	C27—H27A	0.9700
N9—H9N	0.880 (10)	C27—H27B	0.9700
C1—C2	1.378 (9)	C28—C29	1.389 (8)
C1—H1A	0.9300	C28—C33	1.391 (8)
C2—C3	1.366 (9)	C29—C30	1.373 (9)
C2—H2A	0.9300	C29—H29	0.9300
C3—H3A	0.9300	C30—C31	1.373 (10)
C5—C6	1.513 (9)	C30—H30	0.9300
C5—H5A	0.9700	C31—C32	1.378 (9)
C5—H5B	0.9700	C31—H31	0.9300
C6—C7	1.376 (9)	C32—C33	1.388 (9)
C6—C11	1.400 (8)	C32—H32	0.9300

N1—Ag1—N4	174.16 (17)	N4—C12—H12	119.0
N1—Ag1—N7	95.84 (18)	C13—C12—H12	119.0
N4—Ag1—N7	85.61 (17)	C12—C13—C14	116.9 (6)
N1—Ag1—O4	90.50 (16)	C12—C13—H13	121.6
N4—Ag1—O4	95.16 (17)	C14—C13—H13	121.6
N7—Ag1—O4	90.16 (16)	N5—C14—C13	123.3 (6)
C11—O1—H1O	107 (6)	N5—C14—H14	118.3
C22—O2—H2O	112 (6)	C13—C14—H14	118.3
C33—O3—H3O	109 (6)	N6—C15—N5	119.3 (5)
N10—O4—Ag1	135.7 (4)	N6—C15—N4	116.5 (5)
C1—N1—C4	116.4 (5)	N5—C15—N4	124.2 (5)
C1—N1—Ag1	115.5 (4)	N6—C16—C17	114.9 (5)
C4—N1—Ag1	124.1 (4)	N6—C16—H16A	108.6
C3—N2—C4	117.4 (5)	C17—C16—H16A	108.6
C4—N3—C5	123.6 (5)	N6—C16—H16B	108.6
C4—N3—H3N	122 (4)	C17—C16—H16B	108.6
C5—N3—H3N	113 (4)	H16A—C16—H16B	107.5
C12—N4—C15	117.1 (5)	C18—C17—C22	118.0 (6)
C12—N4—Ag1	119.2 (4)	C18—C17—C16	124.4 (5)
C15—N4—Ag1	123.0 (4)	C22—C17—C16	117.7 (6)
C14—N5—C15	116.4 (5)	C17—C18—C19	121.7 (6)
C15—N6—C16	126.0 (5)	C17—C18—H18	119.2
C15—N6—H6N	119 (4)	C19—C18—H18	119.2
C16—N6—H6N	114 (4)	C18—C19—C20	118.6 (7)
C23—N7—C26	116.5 (6)	C18—C19—H19	120.7
C23—N7—Ag1	109.1 (4)	C20—C19—H19	120.7
C26—N7—Ag1	125.0 (5)	C21—C20—C19	121.1 (7)
C25—N8—C26	115.9 (6)	C21—C20—H20	119.4
C26—N9—C27	123.6 (5)	C19—C20—H20	119.4
C26—N9—H9N	110 (4)	C22—C21—C20	119.6 (7)
C27—N9—H9N	122 (4)	C22—C21—H21	120.2
O6—N10—O5	122.5 (7)	C20—C21—H21	120.2
O6—N10—O4	118.0 (6)	O2—C22—C21	123.5 (6)
O5—N10—O4	119.4 (7)	O2—C22—C17	115.4 (6)
N1—C1—C2	123.4 (6)	C21—C22—C17	121.0 (7)
N1—C1—H1A	118.3	N7—C23—C24	123.8 (7)
C2—C1—H1A	118.3	N7—C23—H23	118.1
C3—C2—C1	116.0 (6)	C24—C23—H23	118.1
C3—C2—H2A	122.0	C25—C24—C23	115.5 (8)
C1—C2—H2A	122.0	C25—C24—H24	122.2
N2—C3—C2	122.8 (6)	C23—C24—H24	122.2
N2—C3—H3A	118.6	N8—C25—C24	123.7 (7)
C2—C3—H3A	118.6	N8—C25—H25	118.2
N3—C4—N2	119.0 (5)	C24—C25—H25	118.2
N3—C4—N1	117.3 (5)	N9—C26—N7	117.7 (6)
N2—C4—N1	123.6 (5)	N9—C26—N8	118.1 (6)
N3—C5—C6	114.3 (6)	N7—C26—N8	124.2 (6)
N3—C5—H5A	108.7	N9—C27—C28	114.5 (5)
C6—C5—H5A	108.7	N9—C27—H27A	108.6
N3—C5—H5B	108.7	C28—C27—H27A	108.6
C6—C5—H5B	108.7	N9—C27—H27B	108.6
H5A—C5—H5B	107.6	C28—C27—H27B	108.6
C7—C6—C11	117.5 (6)	H27A—C27—H27B	107.6
C7—C6—C5	124.1 (5)	C29—C28—C33	118.0 (6)
C11—C6—C5	118.4 (6)	C29—C28—C27	123.3 (6)
C8—C7—C6	121.9 (6)	C33—C28—C27	118.6 (5)
C8—C7—H7	119.0	C30—C29—C28	121.0 (6)
C6—C7—H7	119.0	C30—C29—H29	119.5
C7—C8—C9	120.4 (7)	C28—C29—H29	119.5
C7—C8—H8	119.8	C29—C30—C31	120.6 (6)
C9—C8—H8	119.8	C29—C30—H30	119.7
C10—C9—C8	119.2 (7)	C31—C30—H30	119.7
C10—C9—H9	120.4	C30—C31—C32	119.6 (7)
C8—C9—H9	120.4	C30—C31—H31	120.2
C9—C10—C11	120.0 (6)	C32—C31—H31	120.2
C9—C10—H10	120.0	C31—C32—C33	120.1 (6)
C11—C10—H10	120.0	C31—C32—H32	119.9
O1—C11—C10	122.8 (6)	C33—C32—H32	119.9
O1—C11—C6	116.3 (6)	O3—C33—C32	122.8 (5)
C10—C11—C6	120.9 (6)	O3—C33—C28	116.6 (6)
N4—C12—C13	122.1 (6)	C32—C33—C28	120.6 (6)

N1—Ag1—O4—N10	−128.7 (6)	C12—C13—C14—N5	−0.1 (10)
N4—Ag1—O4—N10	52.8 (6)	C16—N6—C15—N5	5.0 (10)
N7—Ag1—O4—N10	−32.9 (6)	C16—N6—C15—N4	−175.2 (6)
N7—Ag1—N1—C1	122.7 (4)	C14—N5—C15—N6	179.8 (6)
O4—Ag1—N1—C1	−147.1 (4)	C14—N5—C15—N4	0.1 (9)
N7—Ag1—N1—C4	−34.0 (5)	C12—N4—C15—N6	179.3 (5)
O4—Ag1—N1—C4	56.2 (4)	Ag1—N4—C15—N6	−10.6 (7)
N7—Ag1—N4—C12	108.4 (4)	C12—N4—C15—N5	−1.0 (8)
O4—Ag1—N4—C12	18.7 (5)	Ag1—N4—C15—N5	169.1 (4)
N7—Ag1—N4—C15	−61.5 (4)	C15—N6—C16—C17	−84.9 (8)
O4—Ag1—N4—C15	−151.3 (4)	N6—C16—C17—C18	−1.4 (9)
N1—Ag1—N7—C23	132.8 (5)	N6—C16—C17—C22	178.5 (5)
N4—Ag1—N7—C23	−52.8 (5)	C22—C17—C18—C19	−1.3 (9)
O4—Ag1—N7—C23	42.3 (5)	C16—C17—C18—C19	178.5 (6)
N1—Ag1—N7—C26	−12.2 (5)	C17—C18—C19—C20	1.2 (10)
N4—Ag1—N7—C26	162.2 (5)	C18—C19—C20—C21	−1.8 (11)
O4—Ag1—N7—C26	−102.7 (5)	C19—C20—C21—C22	2.4 (11)
Ag1—O4—N10—O6	77.5 (8)	C20—C21—C22—O2	178.3 (7)
Ag1—O4—N10—O5	−106.3 (7)	C20—C21—C22—C17	−2.5 (11)
C4—N1—C1—C2	2.2 (9)	C18—C17—C22—O2	−178.8 (6)
Ag1—N1—C1—C2	−156.3 (5)	C16—C17—C22—O2	1.3 (8)
N1—C1—C2—C3	2.7 (10)	C18—C17—C22—C21	2.0 (9)
C4—N2—C3—C2	−0.2 (10)	C16—C17—C22—C21	−177.9 (6)
C1—C2—C3—N2	−3.7 (10)	C26—N7—C23—C24	0.0 (11)
C5—N3—C4—N2	0.7 (9)	Ag1—N7—C23—C24	−148.3 (7)
C5—N3—C4—N1	179.8 (6)	N7—C23—C24—C25	5.0 (12)
C3—N2—C4—N3	−175.2 (6)	C26—N8—C25—C24	0.5 (12)
C3—N2—C4—N1	5.8 (9)	C23—C24—C25—N8	−5.2 (13)
C1—N1—C4—N3	174.3 (5)	C27—N9—C26—N7	−170.8 (6)
Ag1—N1—C4—N3	−29.2 (7)	C27—N9—C26—N8	9.7 (9)
C1—N1—C4—N2	−6.7 (9)	C23—N7—C26—N9	175.1 (6)
Ag1—N1—C4—N2	149.8 (5)	Ag1—N7—C26—N9	−42.1 (7)
C4—N3—C5—C6	74.2 (8)	C23—N7—C26—N8	−5.5 (9)
N3—C5—C6—C7	4.3 (9)	Ag1—N7—C26—N8	137.3 (5)
N3—C5—C6—C11	−176.3 (5)	C25—N8—C26—N9	−175.4 (6)
C11—C6—C7—C8	−0.9 (9)	C25—N8—C26—N7	5.2 (10)
C5—C6—C7—C8	178.6 (6)	C26—N9—C27—C28	68.8 (8)
C6—C7—C8—C9	0.4 (10)	N9—C27—C28—C29	7.2 (9)
C7—C8—C9—C10	0.2 (11)	N9—C27—C28—C33	−172.4 (5)
C8—C9—C10—C11	−0.2 (11)	C33—C28—C29—C30	−3.0 (9)
C9—C10—C11—O1	179.4 (6)	C27—C28—C29—C30	177.4 (6)
C9—C10—C11—C6	−0.4 (10)	C28—C29—C30—C31	2.1 (11)
C7—C6—C11—O1	−178.9 (6)	C29—C30—C31—C32	−1.2 (11)
C5—C6—C11—O1	1.7 (8)	C30—C31—C32—C33	1.3 (10)
C7—C6—C11—C10	0.9 (9)	C31—C32—C33—O3	179.3 (6)
C5—C6—C11—C10	−178.6 (6)	C31—C32—C33—C28	−2.3 (10)
C15—N4—C12—C13	1.4 (9)	C29—C28—C33—O3	−178.4 (5)
Ag1—N4—C12—C13	−169.1 (5)	C27—C28—C33—O3	1.2 (8)
N4—C12—C13—C14	−0.9 (10)	C29—C28—C33—C32	3.1 (9)
C15—N5—C14—C13	0.5 (10)	C27—C28—C33—C32	−177.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N8ⁱ	0.84 (1)	2.00 (3)	2.800 (7)	158 (9)
O2—H2o···N5ⁱⁱ	0.84 (1)	1.95 (1)	2.788 (6)	177 (9)
O3—H3o···N2ⁱⁱⁱ	0.84 (1)	1.99 (2)	2.818 (6)	171 (8)
N3—H3n···O4	0.88 (1)	2.22 (2)	3.073 (7)	164 (6)
N6—H6n···O5^iv	0.88 (1)	2.09 (4)	2.879 (8)	149 (6)
N9—H9n···O6^iv	0.88 (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.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₁H₁₁N₃O)₃]NO₃
M_r	773.56
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5987 (4), 13.7931 (7), 16.1308 (10)
α, β, γ (°)	89.159 (2), 88.236 (2), 82.777 (1)
V (Å³)	1676.35 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.852, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	16545, 7609, 3959
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.177, 1.05
No. of reflections	7609
No. of parameters	470
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.17, −1.20

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N8ⁱ	0.84 (1)	2.00 (3)	2.800 (7)	158 (9)
O2—H2o···N5ⁱⁱ	0.84 (1)	1.95 (1)	2.788 (6)	177 (9)
O3—H3o···N2ⁱⁱⁱ	0.84 (1)	1.99 (2)	2.818 (6)	171 (8)
N3—H3n···O4	0.88 (1)	2.22 (2)	3.073 (7)	164 (6)
N6—H6n···O5^iv	0.88 (1)	2.09 (4)	2.879 (8)	149 (6)
N9—H9n···O6^iv	0.88 (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

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

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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
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