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

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⋯Onitrate inter-actions [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 = 773.56

Triclinic,

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[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.177

S = 1.05

7609 reflections

470 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.17 e Å−3

Δρmin = −1.20 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/S1600536812046119/xu5645sup1.cif

Click here for additional data file.

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

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

[Ag(C11H11N3O)3]NO3	Z = 2
Mr = 773.56	F(000) = 792
Triclinic, P1	Dx = 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

Rigaku R-AXIS RAPID IP diffractometer	7609 independent reflections
Radiation source: fine-focus sealed tube	3959 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.852, Tmax = 0.907	k = −17→16
16545 measured reflections	l = −20→20

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(Fo2) + (0.0548P)2 + 4.1203P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
7609 reflections	Δρmax = 1.17 e Å−3
470 parameters	Δρmin = −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)

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O5iv	0.88 (1)	2.09 (4)	2.879 (8)	149 (6)
N9—H9n···O6iv	0.88 (1)	2.28 (4)	3.033 (8)	143 (6)

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⋯O5iv	0.88 (1)	2.09 (4)	2.879 (8)	149 (6)
N9—H9n⋯O6iv	0.88 (1)	2.28 (4)	3.033 (8)	143 (6)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .