Poly[[aqua­[μ5-5-(isonicotinamido)­isophthalato][μ4-5-(isonicotinamido)­isophthalato]holmium(III)silver(I)] dihydrate]

Nie, X.; Qu, J.-N.

doi:10.1107/S1600536812028620

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m1004-m1005

https://doi.org/10.1107/S1600536812028620

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Poly[[aqua[μ₅-5-(isonicotinamido)isophthalato][μ₄-5-(isonicotinamido)isophthalato]holmium(III)silver(I)] dihydrate]

Xue Nie ^a ^* and Jing-Nian Qu ^a

^aDepartment of Chemistry and Materials Science, Hengyang Normal University, Hengyang Hunan 421008, People's Republic of China
^*Correspondence e-mail: hyxuehuanie@163.com

(Received 9 June 2012; accepted 24 June 2012; online 30 June 2012)

The title heteronuclear complex, {[AgHo(C₁₄H₈N₂O₅)₂(H₂O)]·2H₂O}_n, has a three-dimensional polymeric structure, generated by the carboxylate 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 molecule in a distorted square-antiprismatic geometry, while the Ag^I atom has a distorted trigonal-planar AgN₂O geometry. Intermolecular 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_r = 895.30
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.03
5273 reflections
424 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.37 e Å⁻³
Δρ_min = −1.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3Wⁱ	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⋯O10^iv	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⋯O9^vii	0.85	2.22	2.766 (8)	122
O3W—H3X⋯N2^viii	0.85	2.49	3.187 (9)	140
O3W—H3Y⋯O9^ix	0.85	2.30	2.821 (7)	120
Symmetry codes: (i) x-1, y, z+1; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+2, -z+2; (iv) x, y, z+1; (v) x-1, y, z; (vi) x, y-1, z-1; (vii) -x, -y+1, -z+1; (viii) -x+1, -y+1, -z+2; (ix) x+1, y-1, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812028620/xu5562sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028620/xu5562Isup2.hkl

checkCIF report

Comment top

Recently, coordination polymeric frameworks have attracted great attention due to their potential applications and intriguing structure topologies (Kapoor et al., 2002; Abourahma et al., 2002; Costes et al., 2004). However, to obtain d-f coordination polymers is more important. On the other hand, multidentate ligands containing both N– and O-donor atoms are usually employed in the construction of Lanthanide and transiton metal heterometallic structures, in keeping with the typical coordination behaviors of Ln and M ions under different reaction conditions (Zhang et al., 2005; Cheng et al., 2006; Lin et al., 2009). To the best of our knowledge, 5-(isonicotinamido)isophthalic acid (H₂INAIP) can show richer coordination modes due to its two carboxylate groups and one pyridyl group, accordingly, it is an excellent candidate for the construction of metal organic frameworks (Chen et al., 2010). In this paper, we report on the synthesis and crystal structure of a 4d-4f heterometallic coordination polymer (I).

It is interesting that two INAIP^2- ligands exhibit different coordination modes: one coordinated to three Ho^III atoms and two Ag^I atoms while the other coordinated to three Ho^III atoms and one Ag^I atom, originated from the different coordination modes of the carboxylate groups. When the Ag—N and Ag—O connections are neglected, a two-dimensional (4,4) bilayer network is formed by Ho(III)-carboxylate groups, which is similar complex [AgCe(C₁₄H₈N₂O₅)₂(H₂O)]_n (Nie et al., 2011). Then the two-dimensional (4,4) nets are linked together by Ag—N and Ag—O coordination interaction to form a complicated three-dimensional supramolecular net (Fig. 2), which is isomorphous to its AgEr isologue {[AgEr(INAIP)₂(H₂O)].H₂O}_n (Chen et al., 2010).

Related literature top

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 top

A mixture of 0.05 mmol Ho(NO₃)₃.6H₂O (23.0 mg, 0.05 mmol), H₂INAIP (28.6 mg, 0.1 mmol), AgNO₃ (8.5 mg, 0.05 mmol), NaOH (6.0 mg, 0.15 mmol) and H₂O (10 ml) was heated in a 16 mL capacity Teflon-lined reaction vessel at 453 K for 4 d, the reaction mixture was cooled to room temperature over a period of 40 h. The product was collected by filtration.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. Projection showing the three-dimensional structure of the compound (I).

Poly[[aqua[µ₅-5-(isonicotinamido)isophthalato][µ₄-5- (isonicotinamido)isophthalato]holmium(III)silver(I)] dihydrate] top

Crystal data top

[AgHo(C₁₄H₈N₂O₅)₂(H₂O)]·2H₂O	Z = 2
M_r = 895.30	F(000) = 872
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEXII CCD diffractometer	5273 independent reflections
Radiation source: sealed tube	4177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
T_min = 0.531, T_max = 0.713	k = −13→12
7445 measured reflections	l = −16→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.065P)² + 1.99P] where P = (F_o² + 2F_c²)/3
5273 reflections	(Δ/σ)_max < 0.001
424 parameters	Δρ_max = 1.37 e Å⁻³
2 restraints	Δρ_min = −1.56 e Å⁻³

Crystal data top

[AgHo(C₁₄H₈N₂O₅)₂(H₂O)]·2H₂O	γ = 83.965 (2)°
M_r = 895.30	V = 1383.6 (3) Å³
Triclinic, P1	Z = 2
a = 9.8343 (13) Å	Mo Kα radiation
b = 11.3087 (15) Å	µ = 3.63 mm⁻¹
c = 13.723 (2) Å	T = 291 K
α = 73.914 (2)°	0.20 × 0.16 × 0.10 mm
β = 70.671 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5273 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4177 reflections with I > 2σ(I)
T_min = 0.531, T_max = 0.713	R_int = 0.024
7445 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	Δρ_max = 1.37 e Å⁻³
5273 reflections	Δρ_min = −1.56 e Å⁻³
424 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—O1^iv	2.225 (5)
C9—O5	1.190 (7)	Ho1—O4	2.256 (4)
C9—N2	1.342 (8)	Ho1—O8^v	2.291 (4)
C9—C10	1.5102 (11)	Ho1—O3^vi	2.313 (4)
C10—C11	1.347 (9)	Ho1—O7^vi	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—Ho1^vii	2.225 (5)
C14—H14	0.9300	O2—Ag1^viii	2.361 (5)
C15—O7	1.241 (9)	O3—Ho1^vi	2.313 (4)
C15—O6	1.252 (9)	O7—Ho1^vi	2.333 (4)
C15—C16	1.488 (10)	O8—Ho1^v	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)	O1^iv—Ho1—O4	149.70 (16)
C4—C3—H3	121.2	O1^iv—Ho1—O8^v	78.68 (18)
C2—C3—H3	121.2	O4—Ho1—O8^v	75.05 (16)
C5—C4—C3	121.5 (6)	O1^iv—Ho1—O3^vi	74.53 (17)
C5—C4—N2	115.8 (6)	O4—Ho1—O3^vi	135.51 (16)
C3—C4—N2	122.5 (6)	O8^v—Ho1—O3^vi	144.42 (16)
C4—C5—C6	121.5 (6)	O1^iv—Ho1—O7^vi	124.68 (18)
C4—C5—H5	119.3	O4—Ho1—O7^vi	72.06 (16)
C6—C5—H5	119.3	O8^v—Ho1—O7^vi	141.58 (16)
C5—C6—C7	119.3 (6)	O3^vi—Ho1—O7^vi	73.90 (16)
C5—C6—C8	125.9 (6)	O1^iv—Ho1—O1W	77.24 (18)
C7—C6—C8	114.3 (6)	O4—Ho1—O1W	82.04 (18)
C2—C7—C6	119.6 (6)	O8^v—Ho1—O1W	76.21 (17)
C2—C7—H7	120.2	O3^vi—Ho1—O1W	119.05 (18)
C6—C7—H7	120.2	O7^vi—Ho1—O1W	80.08 (17)
O2—C8—O1	122.1 (6)	O1^iv—Ho1—O6	96.32 (17)
O2—C8—C6	122.9 (6)	O4—Ho1—O6	89.69 (17)
O1—C8—C6	114.9 (5)	O8^v—Ho1—O6	71.91 (16)
O5—C9—N2	124.8 (5)	O3^vi—Ho1—O6	88.12 (17)
O5—C9—C10	119.3 (5)	O7^vi—Ho1—O6	126.46 (16)
N2—C9—C10	115.8 (5)	O1W—Ho1—O6	148.13 (17)
C11—C10—C14	116.5 (5)	O1^iv—Ho1—O7	131.53 (15)
C11—C10—C9	122.5 (5)	O4—Ho1—O7	73.93 (14)
C14—C10—C9	120.9 (5)	O8^v—Ho1—O7	113.37 (15)
C10—C11—C12	120.5 (6)	O3^vi—Ho1—O7	70.57 (16)
C10—C11—H11	119.7	O7^vi—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	O1^iv—Ho1—C15	115.62 (19)
C11—C12—H12	118.7	O4—Ho1—C15	80.58 (18)
N1—C13—C14	126.5 (7)	O8^v—Ho1—C15	92.40 (18)
N1—C13—H13	116.8	O3^vi—Ho1—C15	78.82 (18)
C14—C13—H13	116.8	O7^vi—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)	O1^iv—Ho1—Ho1^vi	141.56 (12)
O7—C15—C16	120.5 (6)	O4—Ho1—Ho1^vi	68.37 (11)
O6—C15—C16	117.7 (7)	O8^v—Ho1—Ho1^vi	136.93 (12)
O7—C15—Ho1	67.1 (4)	O3^vi—Ho1—Ho1^vi	67.16 (12)
O6—C15—Ho1	54.7 (4)	O7^vi—Ho1—Ho1^vi	40.79 (12)
C16—C15—Ho1	172.3 (5)	O1W—Ho1—Ho1^vi	118.83 (13)
C21—C16—C17	121.6 (6)	O6—Ho1—Ho1^vi	85.69 (11)
C21—C16—C15	119.8 (6)	O7—Ho1—Ho1^vi	34.96 (10)
C17—C16—C15	118.4 (6)	C15—Ho1—Ho1^vi	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—Ho1^vii	129.9 (4)
C21—C20—N4	117.1 (6)	C8—O2—Ag1^viii	123.1 (5)
C19—C20—N4	120.0 (6)	C1—O3—Ho1^vi	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—Ho1^vi	167.9 (5)
O9—C22—O8	121.9 (6)	C15—O7—Ho1	87.5 (4)
O9—C22—C18	117.9 (6)	Ho1^vi—O7—Ho1	104.25 (17)
O8—C22—C18	120.3 (6)	C22—O8—Ho1^v	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—O7^vi	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—Ho1^vi	−1.9 (3)
C2—C3—C4—C5	−7.0 (11)	O6—C15—Ho1—Ho1^vi	−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—Ho1^vii	35.2 (9)
N2—C9—C10—C14	−37.0 (9)	C6—C8—O1—Ho1^vii	−147.7 (5)
C14—C10—C11—C12	2.2 (9)	O1—C8—O2—Ag1^viii	47.6 (8)
C9—C10—C11—C12	178.3 (6)	C6—C8—O2—Ag1^viii	−129.2 (6)
C13—N1—C12—C11	3.1 (10)	O4—C1—O3—Ho1^vi	30.8 (11)
Ag1ⁱⁱⁱ—N1—C12—C11	174.4 (5)	C2—C1—O3—Ho1^vi	−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)	O1^iv—Ho1—O4—C1	−159.5 (6)
N1—C13—C14—C10	2.0 (12)	O8^v—Ho1—O4—C1	169.8 (7)
C11—C10—C14—C13	−1.7 (10)	O3^vi—Ho1—O4—C1	11.4 (8)
C9—C10—C14—C13	−177.8 (6)	O7^vi—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)	Ho1^vi—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)	O1^iv—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)	O8^v—Ho1—O6—C15	−142.5 (5)
C18—C19—C20—C21	−7.1 (10)	O3^vi—Ho1—O6—C15	67.4 (4)
C18—C19—C20—N4	−178.6 (6)	O7^vi—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)	Ho1^vi—Ho1—O6—C15	0.1 (4)
N4—C20—C21—C16	177.8 (6)	O6—C15—O7—Ho1^vi	168.5 (16)
C19—C18—C22—O9	−21.2 (10)	C16—C15—O7—Ho1^vi	−15 (2)
C17—C18—C22—O9	160.5 (6)	Ho1—C15—O7—Ho1^vi	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)	O1^iv—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)	O8^v—Ho1—O7—C15	36.7 (4)
N4—C23—C24—C25	−143.1 (6)	O3^vi—Ho1—O7—C15	−105.2 (4)
C28—C24—C25—C26	1.3 (9)	O7^vi—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)	Ho1^vi—Ho1—O7—C15	177.1 (5)
C23—C24—C28—C27	173.4 (6)	O1^iv—Ho1—O7—Ho1^vi	124.0 (2)
N3—C27—C28—C24	6.5 (11)	O4—Ho1—O7—Ho1^vi	−75.07 (18)
O7—C15—Ho1—O1^iv	134.7 (4)	O8^v—Ho1—O7—Ho1^vi	−140.43 (17)
O6—C15—Ho1—O1^iv	−43.2 (5)	O3^vi—Ho1—O7—Ho1^vi	77.65 (18)
O7—C15—Ho1—O4	−72.3 (4)	O7^vi—Ho1—O7—Ho1^vi	0.0
O6—C15—Ho1—O4	109.8 (4)	O1W—Ho1—O7—Ho1^vi	−37.1 (4)
O7—C15—Ho1—O8^v	−146.7 (4)	O6—Ho1—O7—Ho1^vi	−178.3 (3)
O6—C15—Ho1—O8^v	35.4 (4)	C15—Ho1—O7—Ho1^vi	−177.1 (5)
O7—C15—Ho1—O3^vi	68.1 (4)	O9—C22—O8—Ho1^v	−30.4 (10)
O6—C15—Ho1—O3^vi	−109.9 (4)	C18—C22—O8—Ho1^v	150.3 (5)
O7—C15—Ho1—O7^vi	−2.8 (5)

Symmetry codes: (i) x+1, y+1, z−2; (ii) x+1, y+1, z−1; (iii) x−1, y−1, z+2; (iv) x, y+1, z; (v) −x, −y+2, −z+2; (vi) −x+1, −y+2, −z+2; (vii) x, y−1, z; (viii) x−1, y−1, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3W^ix	0.86	2.11	2.878 (9)	149
N4—H4···O5^vi	0.86	2.08	2.925 (8)	168
O1W—H1X···O9^v	0.85	2.05	2.562 (7)	118
O1W—H1Y···O10^x	0.85	1.90	2.717 (7)	161
O2W—H2X···O3W^xi	0.85	2.11	2.799 (8)	138
O2W—H2Y···O1W^xii	0.85	2.34	3.136 (8)	156
O2W—H2Y···O9^xiii	0.85	2.22	2.766 (8)	122
O3W—H3X···N2^xiv	0.85	2.49	3.187 (9)	140
O3W—H3Y···O9^xv	0.85	2.30	2.821 (7)	120

Symmetry codes: (v) −x, −y+2, −z+2; (vi) −x+1, −y+2, −z+2; (ix) x−1, y, z+1; (x) x, y, z+1; (xi) x−1, y, z; (xii) x, y−1, z−1; (xiii) −x, −y+1, −z+1; (xiv) −x+1, −y+1, −z+2; (xv) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	[AgHo(C₁₄H₈N₂O₅)₂(H₂O)]·2H₂O
M_r	895.30
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.8343 (13), 11.3087 (15), 13.723 (2)
α, β, γ (°)	73.914 (2), 70.671 (1), 83.965 (2)
V (Å³)	1383.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.63
Crystal size (mm)	0.20 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.531, 0.713
No. of measured, independent and observed [I > 2σ(I)] reflections	7445, 5273, 4177
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.03
No. of reflections	5273
No. of parameters	424
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.37, −1.56

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3Wⁱ	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···O10^iv	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···O9^vii	0.85	2.22	2.766 (8)	122
O3W—H3X···N2^viii	0.85	2.49	3.187 (9)	140
O3W—H3Y···O9^ix	0.85	2.30	2.821 (7)	120

Symmetry codes: (i) x−1, y, z+1; (ii) −x+1, −y+2, −z+2; (iii) −x, −y+2, −z+2; (iv) x, y, z+1; (v) x−1, y, z; (vi) x, y−1, z−1; (vii) −x, −y+1, −z+1; (viii) −x+1, −y+1, −z+2; (ix) x+1, y−1, z.

Acknowledgements

This work was supported by the Hengyang Bureau of Science & Technology (grant No. 2009 K J28).

References

Abourahma, H., Moulton, B., Kravtsov, V. & Zaworotko, M. J. (2002). J. Am. Chem. Soc. 124, 9990–9991. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, M.-S., Su, Z., Chen, M., Chen, S.-S., Li, Y.-Z. & Sun, W.-Y. (2010). CrystEngComm, 12, 3267–3276. Web of Science CSD CrossRef CAS Google Scholar
Cheng, J.-W., Zhang, J., Zheng, S.-T., Zhang, M.-B. & Yang, G.-Y. (2006). Angew. Chem. Int. Ed. 45, 73–76. Web of Science CSD CrossRef CAS Google Scholar
Costes, J. P., Dahan, F., Donnadieu, B., Douton, M. J. R., Garcia, M. I. F., Bousseksou, A. & Tuchagues, J. P. (2004). Inorg. Chem. 43, 2736–2744. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kapoor, P., Pathak, A., Kapoor, R., Venugopalan, P., Corbella, M., Rodríguez, M., Robles, J. & Llobet, A. (2002). Inorg. Chem. 41, 6153–6160. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liang, Y.-C., Cao, R., Su, W.-P., Hong, M.-C. & Zhang, W.-J. (2000). Angew. Chem. Int. Ed. 39, 3304–3307. Web of Science CrossRef CAS Google Scholar
Lin, X.-M., Ying, Y., Chen, L., Fang, H.-C., Zhou, Z.-Y., Zhan, Q.-G. & Cai, Y.-P. (2009). Inorg. Chem. Commun. 12, 316–320. Web of Science CSD CrossRef Google Scholar
Nie, X. & Qu, J.-N. (2011). Acta Cryst. E67, m1107–m1108. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, M.-B., Zhang, J., Zheng, S.-T. & Yang, G.-Y. (2005). Angew. Chem. Int. Ed. 44, 1385–1388. Web of Science CSD CrossRef CAS Google Scholar
Zhao, B., Cheng, P., Chen, X.-Y., Cheng, C., Shi, W., Liao, D.-Z., Yan, S.-P. & Jiang, Z.-H. (2004). J. Am. Chem. Soc. 126, 3012–3013. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhao, B., Cheng, P., Dai, Y., Cheng, C., Liao, D.-Z., Yan, S.-P., Jiang, Z.-H. & Wang, G.-L. (2003). Angew. Chem. Int. Ed. 42, 934–936. Web of Science CSD CrossRef CAS Google Scholar

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