Poly[[aqua-[μ(5)-5-(isonicotinamido)-isophthalato][μ(4)-5-(isonicotinamido)-isophthalato]holmium(III)silver(I)] dihydrate].

The title heteronuclear complex, {[AgHo(C(14)H(8)N(2)O(5))(2)(H(2)O)]·2H(2)O}(n), has a three-dimensional polymeric structure, generated by the carboxyl-ate and pyridine groups of the 5-(isonicotinamido)-isophthalate (INAIP) ligands bridging the metal atoms. The Ho(III) atom is coordinated by seven O atoms from INAIP ligands and a water mol-ecule in a distorted square-anti-prismatic geometry, while the Ag(I) atom has a distorted trigonal-planar AgN(2)O geometry. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For background to coordination polymeric frameworks, see: Kapoor et al. (2002 ▶); Abourahma et al. (2002 ▶); Costes et al. (2004 ▶). For related hetero-metallic complexes, see: Chen et al. (2010 ▶); Liang et al. (2000 ▶); Zhao et al. (2003 ▶, 2004 ▶); Nie & Qu (2011 ▶); Zhang et al. (2005 ▶); Cheng et al. (2006 ▶); Lin et al. (2009 ▶).

Experimental

Crystal data

[AgHo(C14H8N2O5)2(H2O)]·2H2O

M = 895.30

Triclinic,

a = 9.8343 (13) Å

b = 11.3087 (15) Å

c = 13.723 (2) Å

α = 73.914 (2)°

β = 70.671 (1)°

γ = 83.965 (2)°

V = 1383.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.63 mm−1

T = 291 K

0.20 × 0.16 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.531, T max = 0.713

7445 measured reflections

5273 independent reflections

4177 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.03

5273 reflections

424 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.37 e Å−3

Δρmin = −1.56 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028620/xu5562sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028620/xu5562Isup2.hkl

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

[AgHo(C14H8N2O5)2(H2O)]·2H2O	Z = 2
Mr = 895.30	F(000) = 872
Triclinic, P1	Dx = 2.149 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8343 (13) Å	Cell parameters from 3132 reflections
b = 11.3087 (15) Å	θ = 2.1–25.3°
c = 13.723 (2) Å	µ = 3.63 mm−1
α = 73.914 (2)°	T = 291 K
β = 70.671 (1)°	Block, colorless
γ = 83.965 (2)°	0.20 × 0.16 × 0.10 mm
V = 1383.6 (3) Å3

Bruker SMART APEXII CCD diffractometer	5273 independent reflections
Radiation source: sealed tube	4177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
Tmin = 0.531, Tmax = 0.713	k = −13→12
7445 measured reflections	l = −16→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.065P)2 + 1.99P] where P = (Fo2 + 2Fc2)/3
5273 reflections	(Δ/σ)max < 0.001
424 parameters	Δρmax = 1.37 e Å−3
2 restraints	Δρmin = −1.56 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ag1	1.04960 (5)	1.30998 (4)	0.01447 (3)	0.02214 (13)
N1	0.1196 (5)	0.3945 (5)	1.8413 (4)	0.0258 (12)
C1	0.3868 (7)	0.7756 (6)	1.0898 (5)	0.0294 (14)
C2	0.3587 (7)	0.6471 (6)	1.1524 (5)	0.0251 (13)
C3	0.3163 (8)	0.6261 (6)	1.2659 (6)	0.0308 (15)
H3	0.3088	0.6906	1.2974	0.037*
C4	0.2868 (7)	0.5064 (6)	1.3275 (5)	0.0270 (14)
C5	0.2826 (7)	0.4137 (7)	1.2831 (6)	0.0300 (15)
H5	0.2614	0.3345	1.3269	0.036*
C6	0.3089 (7)	0.4344 (6)	1.1751 (5)	0.0275 (14)
C7	0.3509 (7)	0.5518 (6)	1.1080 (6)	0.0287 (15)
H7	0.3734	0.5662	1.0344	0.034*
C8	0.2794 (7)	0.3470 (6)	1.1205 (5)	0.0236 (13)
C9	0.2932 (7)	0.5305 (6)	1.4989 (4)	0.0264 (14)
C10	0.2362 (6)	0.4795 (5)	1.6187 (4)	0.0205 (12)
C11	0.3136 (7)	0.4793 (6)	1.6833 (5)	0.0261 (13)
H11	0.4068	0.5096	1.6541	0.031*
C12	0.2550 (8)	0.4341 (6)	1.7940 (5)	0.0289 (14)
H12	0.3125	0.4313	1.8364	0.035*
C13	0.0468 (8)	0.3953 (6)	1.7772 (5)	0.0292 (14)
H13	−0.0463	0.3649	1.8087	0.035*
C14	0.0931 (7)	0.4361 (7)	1.6693 (5)	0.0317 (15)
H14	0.0329	0.4357	1.6295	0.038*
C15	0.3121 (8)	1.0833 (6)	0.9041 (5)	0.0316 (15)
C16	0.2768 (8)	1.1040 (6)	0.8032 (5)	0.0293 (14)
C17	0.1427 (7)	1.0716 (7)	0.8095 (5)	0.0309 (15)
H17	0.0730	1.0425	0.8752	0.037*
C18	0.1136 (7)	1.0844 (7)	0.7096 (5)	0.0281 (14)
C19	0.2151 (8)	1.1266 (6)	0.6153 (5)	0.0282 (14)
H19	0.1951	1.1397	0.5515	0.034*
C20	0.3512 (7)	1.1504 (6)	0.6155 (5)	0.0259 (14)
C21	0.3801 (6)	1.1449 (6)	0.7074 (5)	0.0211 (12)
H21	0.4693	1.1688	0.7046	0.025*
C22	−0.0289 (7)	1.0459 (5)	0.7172 (5)	0.0238 (13)
C23	0.4874 (7)	1.1543 (6)	0.4272 (5)	0.0263 (14)
C24	0.6258 (7)	1.1979 (6)	0.3365 (5)	0.0261 (13)
C25	0.6156 (7)	1.2202 (6)	0.2338 (5)	0.0245 (13)
H25	0.5284	1.2121	0.2238	0.029*
C26	0.7390 (7)	1.2549 (6)	0.1470 (6)	0.0292 (14)
H26	0.7324	1.2708	0.0785	0.035*
C27	0.8703 (7)	1.2411 (7)	0.2579 (5)	0.0287 (14)
H27	0.9591	1.2431	0.2677	0.034*
C28	0.7498 (7)	1.2132 (6)	0.3449 (5)	0.0276 (14)
H28	0.7569	1.2049	0.4123	0.033*
Ho1	0.34584 (3)	1.06199 (3)	1.10929 (2)	0.02108 (10)
N2	0.2485 (7)	0.4741 (6)	1.4411 (5)	0.0308 (13)
H2	0.1916	0.4130	1.4757	0.037*
N3	0.8624 (6)	1.2658 (6)	0.1574 (4)	0.0304 (13)
N4	0.4619 (6)	1.1984 (5)	0.5160 (4)	0.0255 (11)
H4	0.5143	1.2571	0.5118	0.031*
O1	0.2805 (5)	0.2273 (4)	1.1729 (4)	0.0288 (10)
O2	0.2510 (5)	0.3806 (5)	1.0383 (4)	0.0331 (11)
O3	0.4852 (5)	0.7904 (4)	1.0006 (4)	0.0266 (10)
O4	0.3161 (5)	0.8618 (4)	1.1245 (3)	0.0243 (9)
O5	0.3783 (5)	0.6113 (5)	1.4626 (4)	0.0315 (11)
O6	0.2220 (5)	1.1194 (5)	0.9793 (4)	0.0299 (10)
O7	0.4297 (5)	1.0367 (4)	0.9108 (4)	0.0260 (10)
O8	−0.1050 (5)	0.9720 (4)	0.8033 (4)	0.0262 (10)
O9	−0.0714 (5)	1.0863 (5)	0.6377 (4)	0.0326 (11)
O10	0.4053 (6)	1.0890 (5)	0.4210 (3)	0.0355 (12)
O1W	0.3331 (5)	0.9853 (5)	1.2887 (4)	0.0379 (12)
H1X	0.2912	0.9176	1.3251	0.045*
H1Y	0.3707	1.0249	1.3174	0.045*
O2W	0.0736 (6)	0.1475 (5)	0.3881 (5)	0.0429 (13)
H2X	0.0917	0.1841	0.4287	0.052*
H2Y	0.1332	0.0882	0.3796	0.052*
O3W	0.9981 (5)	0.3256 (4)	0.5043 (4)	0.0349 (12)
H3X	0.9205	0.3620	0.4971	0.042*
H3Y	0.9858	0.2911	0.5700	0.042*

	U11	U22	U33	U12	U13	U23
Ag1	0.0179 (2)	0.0271 (3)	0.0160 (2)	−0.00653 (18)	0.00087 (17)	−0.00215 (18)
N1	0.015 (2)	0.039 (3)	0.021 (3)	−0.007 (2)	0.006 (2)	−0.015 (2)
C1	0.024 (3)	0.031 (4)	0.027 (3)	−0.012 (3)	0.002 (3)	−0.005 (3)
C2	0.030 (3)	0.018 (3)	0.022 (3)	0.004 (2)	−0.006 (3)	−0.003 (2)
C3	0.044 (4)	0.010 (3)	0.034 (4)	−0.010 (3)	−0.008 (3)	−0.001 (3)
C4	0.030 (3)	0.034 (4)	0.014 (3)	−0.012 (3)	−0.006 (3)	0.001 (3)
C5	0.016 (3)	0.033 (4)	0.034 (4)	−0.012 (3)	0.002 (3)	−0.005 (3)
C6	0.035 (4)	0.027 (4)	0.017 (3)	−0.005 (3)	−0.003 (3)	−0.005 (3)
C7	0.024 (3)	0.015 (3)	0.036 (4)	0.002 (2)	−0.003 (3)	0.002 (3)
C8	0.020 (3)	0.027 (3)	0.018 (3)	−0.004 (2)	−0.002 (2)	−0.001 (2)
C9	0.030 (3)	0.026 (3)	0.030 (3)	−0.006 (3)	−0.012 (3)	−0.013 (3)
C10	0.026 (3)	0.012 (3)	0.026 (3)	−0.007 (2)	−0.007 (3)	−0.005 (2)
C11	0.030 (3)	0.019 (3)	0.025 (3)	−0.008 (2)	−0.004 (3)	−0.001 (2)
C12	0.037 (4)	0.026 (3)	0.020 (3)	−0.005 (3)	−0.007 (3)	−0.002 (3)
C13	0.033 (4)	0.033 (4)	0.023 (3)	−0.008 (3)	−0.010 (3)	−0.005 (3)
C14	0.023 (3)	0.044 (4)	0.023 (3)	−0.011 (3)	0.002 (3)	−0.008 (3)
C15	0.031 (4)	0.025 (4)	0.024 (3)	−0.008 (3)	0.004 (3)	0.004 (3)
C16	0.039 (4)	0.024 (3)	0.020 (3)	0.005 (3)	−0.012 (3)	0.003 (2)
C17	0.016 (3)	0.053 (5)	0.018 (3)	−0.003 (3)	0.002 (2)	−0.007 (3)
C18	0.014 (3)	0.039 (4)	0.026 (3)	−0.007 (3)	0.003 (2)	−0.006 (3)
C19	0.045 (4)	0.018 (3)	0.027 (3)	−0.007 (3)	−0.018 (3)	−0.003 (2)
C20	0.020 (3)	0.020 (3)	0.032 (3)	0.009 (2)	−0.004 (3)	−0.007 (3)
C21	0.018 (3)	0.021 (3)	0.029 (3)	−0.002 (2)	−0.013 (2)	−0.005 (2)
C22	0.020 (3)	0.011 (3)	0.034 (3)	−0.001 (2)	−0.001 (3)	−0.006 (2)
C23	0.031 (3)	0.026 (3)	0.020 (3)	−0.009 (3)	0.000 (3)	−0.009 (3)
C24	0.029 (3)	0.019 (3)	0.028 (3)	0.000 (2)	−0.003 (3)	−0.007 (3)
C25	0.023 (3)	0.017 (3)	0.032 (3)	0.005 (2)	−0.009 (3)	−0.006 (2)
C26	0.026 (3)	0.024 (3)	0.028 (3)	−0.002 (3)	0.000 (3)	−0.001 (3)
C27	0.020 (3)	0.041 (4)	0.024 (3)	−0.004 (3)	−0.003 (3)	−0.009 (3)
C28	0.032 (4)	0.019 (3)	0.024 (3)	−0.003 (3)	0.001 (3)	−0.005 (2)
Ho1	0.01787 (16)	0.02171 (16)	0.01800 (15)	−0.00186 (10)	−0.00121 (11)	−0.00102 (10)
N2	0.037 (3)	0.033 (3)	0.024 (3)	−0.008 (3)	−0.003 (2)	−0.015 (2)
N3	0.030 (3)	0.039 (3)	0.016 (3)	−0.006 (2)	0.001 (2)	−0.003 (2)
N4	0.029 (3)	0.027 (3)	0.014 (2)	−0.012 (2)	0.001 (2)	0.000 (2)
O1	0.030 (2)	0.027 (2)	0.020 (2)	0.0043 (19)	−0.0004 (19)	−0.0024 (18)
O2	0.031 (3)	0.046 (3)	0.030 (3)	−0.003 (2)	−0.012 (2)	−0.018 (2)
O3	0.025 (2)	0.021 (2)	0.025 (2)	0.0010 (18)	−0.0009 (19)	0.0004 (17)
O4	0.021 (2)	0.023 (2)	0.020 (2)	−0.0115 (18)	0.0050 (17)	−0.0019 (17)
O5	0.031 (3)	0.034 (3)	0.030 (3)	−0.010 (2)	−0.009 (2)	−0.007 (2)
O6	0.028 (2)	0.045 (3)	0.020 (2)	0.010 (2)	−0.0083 (19)	−0.016 (2)
O7	0.020 (2)	0.019 (2)	0.029 (2)	0.0000 (17)	0.0020 (18)	−0.0033 (18)
O8	0.018 (2)	0.030 (2)	0.025 (2)	−0.0024 (18)	−0.0029 (18)	−0.0022 (19)
O9	0.033 (3)	0.037 (3)	0.018 (2)	−0.010 (2)	−0.0044 (19)	0.0075 (19)
O10	0.044 (3)	0.048 (3)	0.014 (2)	−0.028 (3)	0.004 (2)	−0.012 (2)
O1W	0.030 (3)	0.054 (3)	0.027 (3)	−0.002 (2)	−0.007 (2)	−0.007 (2)
O2W	0.046 (3)	0.032 (3)	0.044 (3)	−0.015 (2)	−0.016 (3)	0.006 (2)
O3W	0.033 (3)	0.029 (3)	0.037 (3)	−0.010 (2)	−0.012 (2)	0.006 (2)

Ag1—N3	2.178 (5)	C18—C22	1.473 (9)
Ag1—N1i	2.198 (5)	C19—C20	1.393 (10)
Ag1—O2ii	2.361 (5)	C19—H19	0.9300
N1—C13	1.304 (8)	C20—C21	1.366 (9)
N1—C12	1.337 (9)	C20—N4	1.440 (8)
N1—Ag1iii	2.198 (5)	C21—H21	0.9300
C1—O4	1.248 (9)	C22—O9	1.249 (8)
C1—O3	1.265 (8)	C22—O8	1.285 (8)
C1—C2	1.469 (9)	C23—O10	1.187 (8)
C2—C7	1.396 (10)	C23—N4	1.381 (8)
C2—C3	1.430 (10)	C23—C24	1.524 (9)
C3—C4	1.385 (9)	C24—C28	1.295 (10)
C3—H3	0.9300	C24—C25	1.398 (9)
C4—C5	1.360 (10)	C25—C26	1.389 (9)
C4—N2	1.425 (8)	C25—H25	0.9300
C5—C6	1.373 (10)	C26—N3	1.290 (9)
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.402 (9)	C27—N3	1.357 (9)
C6—C8	1.496 (9)	C27—C28	1.364 (9)
C7—H7	0.9300	C27—H27	0.9300
C8—O2	1.201 (8)	C28—H28	0.9300
C8—O1	1.347 (8)	Ho1—O1iv	2.225 (5)
C9—O5	1.190 (7)	Ho1—O4	2.256 (4)
C9—N2	1.342 (8)	Ho1—O8v	2.291 (4)
C9—C10	1.5102 (11)	Ho1—O3vi	2.313 (4)
C10—C11	1.347 (9)	Ho1—O7vi	2.333 (4)
C10—C14	1.418 (9)	Ho1—O1W	2.337 (5)
C11—C12	1.397 (9)	Ho1—O6	2.391 (4)
C11—H11	0.9300	Ho1—O7	2.660 (5)
C12—H12	0.9300	N2—H2	0.8600
C13—C14	1.353 (9)	N4—H4	0.8600
C13—H13	0.9300	O1—Ho1vii	2.225 (5)
C14—H14	0.9300	O2—Ag1viii	2.361 (5)
C15—O7	1.241 (9)	O3—Ho1vi	2.313 (4)
C15—O6	1.252 (9)	O7—Ho1vi	2.333 (4)
C15—C16	1.488 (10)	O8—Ho1v	2.291 (4)
C15—Ho1	2.885 (7)	O1W—H1X	0.8501
C16—C21	1.361 (9)	O1W—H1Y	0.8500
C16—C17	1.375 (10)	O2W—H2X	0.8500
C17—C18	1.457 (9)	O2W—H2Y	0.8500
C17—H17	0.9300	O3W—H3X	0.8500
C18—C19	1.342 (9)	O3W—H3Y	0.8500
N3—Ag1—N1i	144.2 (2)	C26—C25—C24	118.3 (6)
N3—Ag1—O2ii	115.2 (2)	C26—C25—H25	120.8
N1i—Ag1—O2ii	93.50 (18)	C24—C25—H25	120.8
C13—N1—C12	115.7 (6)	N3—C26—C25	122.8 (7)
C13—N1—Ag1iii	125.4 (4)	N3—C26—H26	118.6
C12—N1—Ag1iii	118.3 (4)	C25—C26—H26	118.6
O4—C1—O3	123.9 (6)	N3—C27—C28	120.9 (6)
O4—C1—C2	120.8 (6)	N3—C27—H27	119.5
O3—C1—C2	115.3 (6)	C28—C27—H27	119.5
C7—C2—C3	119.8 (6)	C24—C28—C27	122.2 (7)
C7—C2—C1	123.4 (6)	C24—C28—H28	118.9
C3—C2—C1	116.1 (6)	C27—C28—H28	118.9
C4—C3—C2	117.7 (6)	O1iv—Ho1—O4	149.70 (16)
C4—C3—H3	121.2	O1iv—Ho1—O8v	78.68 (18)
C2—C3—H3	121.2	O4—Ho1—O8v	75.05 (16)
C5—C4—C3	121.5 (6)	O1iv—Ho1—O3vi	74.53 (17)
C5—C4—N2	115.8 (6)	O4—Ho1—O3vi	135.51 (16)
C3—C4—N2	122.5 (6)	O8v—Ho1—O3vi	144.42 (16)
C4—C5—C6	121.5 (6)	O1iv—Ho1—O7vi	124.68 (18)
C4—C5—H5	119.3	O4—Ho1—O7vi	72.06 (16)
C6—C5—H5	119.3	O8v—Ho1—O7vi	141.58 (16)
C5—C6—C7	119.3 (6)	O3vi—Ho1—O7vi	73.90 (16)
C5—C6—C8	125.9 (6)	O1iv—Ho1—O1W	77.24 (18)
C7—C6—C8	114.3 (6)	O4—Ho1—O1W	82.04 (18)
C2—C7—C6	119.6 (6)	O8v—Ho1—O1W	76.21 (17)
C2—C7—H7	120.2	O3vi—Ho1—O1W	119.05 (18)
C6—C7—H7	120.2	O7vi—Ho1—O1W	80.08 (17)
O2—C8—O1	122.1 (6)	O1iv—Ho1—O6	96.32 (17)
O2—C8—C6	122.9 (6)	O4—Ho1—O6	89.69 (17)
O1—C8—C6	114.9 (5)	O8v—Ho1—O6	71.91 (16)
O5—C9—N2	124.8 (5)	O3vi—Ho1—O6	88.12 (17)
O5—C9—C10	119.3 (5)	O7vi—Ho1—O6	126.46 (16)
N2—C9—C10	115.8 (5)	O1W—Ho1—O6	148.13 (17)
C11—C10—C14	116.5 (5)	O1iv—Ho1—O7	131.53 (15)
C11—C10—C9	122.5 (5)	O4—Ho1—O7	73.93 (14)
C14—C10—C9	120.9 (5)	O8v—Ho1—O7	113.37 (15)
C10—C11—C12	120.5 (6)	O3vi—Ho1—O7	70.57 (16)
C10—C11—H11	119.7	O7vi—Ho1—O7	75.75 (17)
C12—C11—H11	119.7	O1W—Ho1—O7	150.06 (17)
N1—C12—C11	122.7 (6)	O6—Ho1—O7	50.74 (15)
N1—C12—H12	118.7	O1iv—Ho1—C15	115.62 (19)
C11—C12—H12	118.7	O4—Ho1—C15	80.58 (18)
N1—C13—C14	126.5 (7)	O8v—Ho1—C15	92.40 (18)
N1—C13—H13	116.8	O3vi—Ho1—C15	78.82 (18)
C14—C13—H13	116.8	O7vi—Ho1—C15	101.17 (19)
C13—C14—C10	118.1 (6)	O1W—Ho1—C15	161.2 (2)
C13—C14—H14	121.0	O6—Ho1—C15	25.30 (18)
C10—C14—H14	121.0	O7—Ho1—C15	25.45 (17)
O7—C15—O6	121.8 (7)	O1iv—Ho1—Ho1vi	141.56 (12)
O7—C15—C16	120.5 (6)	O4—Ho1—Ho1vi	68.37 (11)
O6—C15—C16	117.7 (7)	O8v—Ho1—Ho1vi	136.93 (12)
O7—C15—Ho1	67.1 (4)	O3vi—Ho1—Ho1vi	67.16 (12)
O6—C15—Ho1	54.7 (4)	O7vi—Ho1—Ho1vi	40.79 (12)
C16—C15—Ho1	172.3 (5)	O1W—Ho1—Ho1vi	118.83 (13)
C21—C16—C17	121.6 (6)	O6—Ho1—Ho1vi	85.69 (11)
C21—C16—C15	119.8 (6)	O7—Ho1—Ho1vi	34.96 (10)
C17—C16—C15	118.4 (6)	C15—Ho1—Ho1vi	60.39 (15)
C16—C17—C18	117.6 (6)	C9—N2—C4	125.9 (6)
C16—C17—H17	121.2	C9—N2—H2	117.1
C18—C17—H17	121.2	C4—N2—H2	117.1
C19—C18—C17	120.6 (6)	C26—N3—C27	117.8 (6)
C19—C18—C22	122.2 (6)	C26—N3—Ag1	118.9 (5)
C17—C18—C22	117.2 (6)	C27—N3—Ag1	123.2 (5)
C18—C19—C20	118.4 (6)	C23—N4—C20	122.8 (6)
C18—C19—H19	120.8	C23—N4—H4	118.6
C20—C19—H19	120.8	C20—N4—H4	118.6
C21—C20—C19	122.4 (6)	C8—O1—Ho1vii	129.9 (4)
C21—C20—N4	117.1 (6)	C8—O2—Ag1viii	123.1 (5)
C19—C20—N4	120.0 (6)	C1—O3—Ho1vi	137.0 (4)
C16—C21—C20	119.2 (6)	C1—O4—Ho1	138.4 (4)
C16—C21—H21	120.4	C15—O6—Ho1	100.0 (4)
C20—C21—H21	120.4	C15—O7—Ho1vi	167.9 (5)
O9—C22—O8	121.9 (6)	C15—O7—Ho1	87.5 (4)
O9—C22—C18	117.9 (6)	Ho1vi—O7—Ho1	104.25 (17)
O8—C22—C18	120.3 (6)	C22—O8—Ho1v	136.1 (4)
O10—C23—N4	122.2 (6)	Ho1—O1W—H1X	120.0
O10—C23—C24	122.3 (6)	Ho1—O1W—H1Y	120.0
N4—C23—C24	115.5 (6)	H1X—O1W—H1Y	120.0
C28—C24—C25	117.7 (6)	H2X—O2W—H2Y	109.5
C28—C24—C23	127.3 (6)	H3X—O3W—H3Y	109.5
C25—C24—C23	115.0 (6)
O4—C1—C2—C7	136.4 (7)	O6—C15—Ho1—O7vi	179.2 (4)
O3—C1—C2—C7	−43.4 (9)	O7—C15—Ho1—O1W	−94.8 (7)
O4—C1—C2—C3	−33.9 (10)	O6—C15—Ho1—O1W	87.2 (7)
O3—C1—C2—C3	146.3 (7)	O7—C15—Ho1—O6	178.0 (7)
C7—C2—C3—C4	8.3 (10)	O6—C15—Ho1—O7	−178.0 (7)
C1—C2—C3—C4	179.0 (6)	O7—C15—Ho1—Ho1vi	−1.9 (3)
C2—C3—C4—C5	−7.0 (11)	O6—C15—Ho1—Ho1vi	−179.8 (5)
C2—C3—C4—N2	177.8 (6)	C10—C9—N2—C4	179.5 (6)
C3—C4—C5—C6	0.7 (11)	C5—C4—N2—C9	153.6 (7)
N2—C4—C5—C6	176.2 (6)	C3—C4—N2—C9	−31.0 (11)
C4—C5—C6—C7	4.5 (11)	C25—C26—N3—C27	0.6 (11)
C4—C5—C6—C8	−167.2 (7)	C25—C26—N3—Ag1	176.3 (5)
C3—C2—C7—C6	−3.4 (10)	C28—C27—N3—C26	−4.1 (11)
C1—C2—C7—C6	−173.4 (6)	C28—C27—N3—Ag1	−179.6 (5)
C5—C6—C7—C2	−3.0 (10)	N1i—Ag1—N3—C26	23.8 (8)
C8—C6—C7—C2	169.6 (6)	O2ii—Ag1—N3—C26	163.9 (5)
C5—C6—C8—O2	150.6 (7)	N1i—Ag1—N3—C27	−160.7 (5)
C7—C6—C8—O2	−21.4 (10)	O2ii—Ag1—N3—C27	−20.6 (6)
C5—C6—C8—O1	−26.4 (10)	O10—C23—N4—C20	12.9 (11)
C7—C6—C8—O1	161.5 (6)	C24—C23—N4—C20	−168.7 (6)
O5—C9—C10—C11	−29.0 (10)	C21—C20—N4—C23	144.5 (7)
N2—C9—C10—C11	147.1 (6)	C19—C20—N4—C23	−43.6 (9)
O5—C9—C10—C14	146.9 (7)	O2—C8—O1—Ho1vii	35.2 (9)
N2—C9—C10—C14	−37.0 (9)	C6—C8—O1—Ho1vii	−147.7 (5)
C14—C10—C11—C12	2.2 (9)	O1—C8—O2—Ag1viii	47.6 (8)
C9—C10—C11—C12	178.3 (6)	C6—C8—O2—Ag1viii	−129.2 (6)
C13—N1—C12—C11	3.1 (10)	O4—C1—O3—Ho1vi	30.8 (11)
Ag1iii—N1—C12—C11	174.4 (5)	C2—C1—O3—Ho1vi	−149.4 (5)
C10—C11—C12—N1	−3.1 (11)	O3—C1—O4—Ho1	−28.5 (11)
C12—N1—C13—C14	−2.6 (11)	C2—C1—O4—Ho1	151.7 (5)
Ag1iii—N1—C13—C14	−173.2 (6)	O1iv—Ho1—O4—C1	−159.5 (6)
N1—C13—C14—C10	2.0 (12)	O8v—Ho1—O4—C1	169.8 (7)
C11—C10—C14—C13	−1.7 (10)	O3vi—Ho1—O4—C1	11.4 (8)
C9—C10—C14—C13	−177.8 (6)	O7vi—Ho1—O4—C1	−30.3 (7)
O7—C15—C16—C21	−39.9 (10)	O1W—Ho1—O4—C1	−112.4 (7)
O6—C15—C16—C21	137.0 (7)	O6—Ho1—O4—C1	98.5 (7)
O7—C15—C16—C17	135.0 (7)	O7—Ho1—O4—C1	49.5 (7)
O6—C15—C16—C17	−48.2 (10)	C15—Ho1—O4—C1	74.7 (7)
C21—C16—C17—C18	−1.0 (11)	Ho1vi—Ho1—O4—C1	13.0 (6)
C15—C16—C17—C18	−175.7 (6)	O7—C15—O6—Ho1	−2.2 (7)
C16—C17—C18—C19	−0.1 (11)	C16—C15—O6—Ho1	−179.0 (5)
C16—C17—C18—C22	178.2 (6)	O1iv—Ho1—O6—C15	141.6 (4)
C17—C18—C19—C20	4.0 (11)	O4—Ho1—O6—C15	−68.2 (4)
C22—C18—C19—C20	−174.3 (6)	O8v—Ho1—O6—C15	−142.5 (5)
C18—C19—C20—C21	−7.1 (10)	O3vi—Ho1—O6—C15	67.4 (4)
C18—C19—C20—N4	−178.6 (6)	O7vi—Ho1—O6—C15	−1.0 (5)
C17—C16—C21—C20	−1.9 (10)	O1W—Ho1—O6—C15	−142.5 (4)
C15—C16—C21—C20	172.8 (6)	O7—Ho1—O6—C15	1.1 (4)
C19—C20—C21—C16	6.1 (10)	Ho1vi—Ho1—O6—C15	0.1 (4)
N4—C20—C21—C16	177.8 (6)	O6—C15—O7—Ho1vi	168.5 (16)
C19—C18—C22—O9	−21.2 (10)	C16—C15—O7—Ho1vi	−15 (2)
C17—C18—C22—O9	160.5 (6)	Ho1—C15—O7—Ho1vi	167 (2)
C19—C18—C22—O8	158.1 (7)	O6—C15—O7—Ho1	2.0 (7)
C17—C18—C22—O8	−20.2 (10)	C16—C15—O7—Ho1	178.7 (6)
O10—C23—C24—C28	−143.0 (8)	O1iv—Ho1—O7—C15	−58.9 (4)
N4—C23—C24—C28	38.7 (10)	O4—Ho1—O7—C15	102.1 (4)
O10—C23—C24—C25	35.3 (10)	O8v—Ho1—O7—C15	36.7 (4)
N4—C23—C24—C25	−143.1 (6)	O3vi—Ho1—O7—C15	−105.2 (4)
C28—C24—C25—C26	1.3 (9)	O7vi—Ho1—O7—C15	177.1 (5)
C23—C24—C25—C26	−177.1 (6)	O1W—Ho1—O7—C15	140.0 (4)
C24—C25—C26—N3	0.8 (10)	O6—Ho1—O7—C15	−1.1 (4)
C25—C24—C28—C27	−4.9 (10)	Ho1vi—Ho1—O7—C15	177.1 (5)
C23—C24—C28—C27	173.4 (6)	O1iv—Ho1—O7—Ho1vi	124.0 (2)
N3—C27—C28—C24	6.5 (11)	O4—Ho1—O7—Ho1vi	−75.07 (18)
O7—C15—Ho1—O1iv	134.7 (4)	O8v—Ho1—O7—Ho1vi	−140.43 (17)
O6—C15—Ho1—O1iv	−43.2 (5)	O3vi—Ho1—O7—Ho1vi	77.65 (18)
O7—C15—Ho1—O4	−72.3 (4)	O7vi—Ho1—O7—Ho1vi	0.0
O6—C15—Ho1—O4	109.8 (4)	O1W—Ho1—O7—Ho1vi	−37.1 (4)
O7—C15—Ho1—O8v	−146.7 (4)	O6—Ho1—O7—Ho1vi	−178.3 (3)
O6—C15—Ho1—O8v	35.4 (4)	C15—Ho1—O7—Ho1vi	−177.1 (5)
O7—C15—Ho1—O3vi	68.1 (4)	O9—C22—O8—Ho1v	−30.4 (10)
O6—C15—Ho1—O3vi	−109.9 (4)	C18—C22—O8—Ho1v	150.3 (5)
O7—C15—Ho1—O7vi	−2.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3Wix	0.86	2.11	2.878 (9)	149
N4—H4···O5vi	0.86	2.08	2.925 (8)	168
O1W—H1X···O9v	0.85	2.05	2.562 (7)	118
O1W—H1Y···O10x	0.85	1.90	2.717 (7)	161
O2W—H2X···O3Wxi	0.85	2.11	2.799 (8)	138
O2W—H2Y···O1Wxii	0.85	2.34	3.136 (8)	156
O2W—H2Y···O9xiii	0.85	2.22	2.766 (8)	122
O3W—H3X···N2xiv	0.85	2.49	3.187 (9)	140
O3W—H3Y···O9xv	0.85	2.30	2.821 (7)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3W i	0.86	2.11	2.878 (9)	149
N4—H4⋯O5ii	0.86	2.08	2.925 (8)	168
O1W—H1X⋯O9iii	0.85	2.05	2.562 (7)	118
O1W—H1Y⋯O10iv	0.85	1.90	2.717 (7)	161
O2W—H2X⋯O3W v	0.85	2.11	2.799 (8)	138
O2W—H2Y⋯O1W vi	0.85	2.34	3.136 (8)	156
O2W—H2Y⋯O9vii	0.85	2.22	2.766 (8)	122
O3W—H3X⋯N2viii	0.85	2.49	3.187 (9)	140
O3W—H3Y⋯O9ix	0.85	2.30	2.821 (7)	120

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .