Bis{μ-2-[(pyrimidin-2-yl)amino­meth­yl]phenolato}-κ2N1:O;κ2O:N1-bis­({2-[(pyrimidin-2-yl-κN)amino­meth­yl]phenol}silver(I)) dihydrate

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812045783

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1538-m1539

doi:10.1107/S1600536812045783

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Bis{μ-2-[(pyrimidin-2-yl)aminomethyl]phenolato}-κ²N¹:O;κ²O:N¹-bis({2-[(pyrimidin-2-yl-κN)aminomethyl]phenol}silver(I)) dihydrate

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 6 November 2012; online 28 November 2012)

The Ag^I 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 Ag^I 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

[Ag₂(C₁₁H₁₀N₃O)₂(C₁₁H₁₁N₃O)₂]·2H₂O
M_r = 1054.67
Monoclinic, P 2₁ /c
a = 9.2992 (4) Å
b = 24.808 (1) Å
c = 9.8158 (5) Å
β = 108.453 (1)°
V = 2148.02 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 K
0.23 × 0.20 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.807, T_max = 0.852
20943 measured reflections
4910 independent reflections
3230 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.133
S = 1.11
4910 reflections
307 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.27 e Å⁻³
Δρ_min = −1.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯N3^iv	0.84 (1)	2.27 (2)	3.085 (5)	165 (6)
N1—H1⋯O1^v	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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) -x+2, -y+1, -z+1.

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/S1600536812045783/xu5644sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045783/xu5644Isup2.hkl

checkCIF report

Comment top

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 Ag^I 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).

Related literature top

For the structure of 2-{[(pyrimidin-2-yl)amino]methyl}phenol, 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-[(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.

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 [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.

Bis{µ-2-[(pyrimidin-2-yl)aminomethyl]phenolato}- κ²N¹:O;κ²O:N¹-bis({2-[(pyrimidin-2- yl-κN)aminomethyl]phenol}silver(I)) dihydrate top

Crystal data top

[Ag₂(C₁₁H₁₀N₃O)₂(C₁₁H₁₁N₃O)₂]·2H₂O	F(000) = 1072
M_r = 1054.67	D_x = 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

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4910 independent reflections
Radiation source: fine-focus sealed tube	3230 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scan	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→11
T_min = 0.807, T_max = 0.852	k = −32→32
20943 measured reflections	l = −12→12

Refinement top

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(F_o²) + (0.0382P)² + 4.7243P] where P = (F_o² + 2F_c²)/3
4910 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 1.27 e Å⁻³
7 restraints	Δρ_min = −1.29 e Å⁻³

Crystal data top

[Ag₂(C₁₁H₁₀N₃O)₂(C₁₁H₁₁N₃O)₂]·2H₂O	V = 2148.02 (17) Å³
M_r = 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)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4910 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3230 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.852	R_int = 0.063
20943 measured reflections

Refinement top

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	Δρ_max = 1.27 e Å⁻³
4910 reflections	Δρ_min = −1.29 e Å⁻³
307 parameters

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.84 (1)	2.31 (6)	2.927 (5)	130 (6)
O1w—H12···N3^v	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
M_r	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)
T_min, T_max	0.807, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	20943, 4910, 3230
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···N3^iv	0.84 (1)	2.27 (2)	3.085 (5)	165 (6)
N1—H1···O1^v	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
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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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