Bis{μ-2-[(pyrimidin-2-yl)amino-meth-yl]phenolato}-κ(2) N (1):O;κ(2) O:N (1)-bis-({2-[(pyrimidin-2-yl-κN)amino-meth-yl]phenol}silver(I)) dihydrate.

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)amino-meth-yl]phenol ligand, the N atom of the 2-[(pyrimidin-2-yl)amino-meth-yl]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)amino-meth-yl]phenolate anions link the two Ag(I) atoms to form the dinuclear compound. In the crystal, adjacent dinuclear mol-ecules are linked to the lattice water mol-ecules, generating an O-H⋯O- and N-H⋯O-connected three-dimensional network. In the crystal, the hy-droxy H atom is disordered over two positions in a 1:1 ratio; one half-occupancy H atom is connected to one hy-droxy group, whereas the other half-occupancy H atom is connected to another hy-droxy 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 = 1054.67

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.133

S = 1.11

4910 reflections

307 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.27 e Å−3

Δρmin = −1.29 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045783/xu5644sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[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

	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)

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)

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⋯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) ; (ii) ; (iii) ; (iv) ; (v) .