Crystal structure of silver [(propane-1,3-diyl­dinitrilo-κ2N,N′)­tetra­acetato-κ4O,O′,O′′,O′′′]chromate(III) from synchrotron X-ray data

Moon, D.; Ryoo, K.S.; Choi, J.-H.

doi:10.1107/S2056989018001743

research communications

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ISSN: 2056-9890

Volume 74| Part 3| March 2018| Pages 278-281

https://doi.org/10.1107/S2056989018001743

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Crystal structure of silver [(propane-1,3-diyldinitrilo-κ²N,N′)tetraacetato-κ⁴O,O′,O′′,O′′′]chromate(III) from synchrotron X-ray data

Dohyun Moon,^a Keon Sang Ryoo ^b and Jong-Ha Choi ^b ^*

^aPohang Accelerator Laboratory, POSTECH, Pohang 37673, Republic of Korea, and ^bDepartment of Chemistry, Andong National University, Andong 36729, Republic of Korea
^*Correspondence e-mail: jhchoi@anu.ac.kr

Edited by G. S. Nichol, University of Edinburgh, Scotland (Received 24 November 2017; accepted 29 January 2018; online 2 February 2018)

The asymmetric unit of the title compound, Ag[Cr(C₁₁H₁₄N₂O₈)]·3H₂O, contains one [Cr(1,3-pdta)]⁻ anion [1,3-pdta is (propane-1,3-diyldinitrilo)tetraacetate], one Ag⁺ cation and three water molecules. The Cr³⁺ ion is coordinated to the four O and two N atoms of the 1,3-pdta ligand, displaying a distorted octahedral geometry. The mean Cr—N and Cr—O bond lengths are 2.0727 (17) and 1.9608 (15) Å, respectively. The conformations of the chelate rings were found to be envelope for the glycinates and twist-boat for the six-membered diamine (T) ring. The Ag⁺ cation is surrounded by six O atoms from three non-coordinated carbonyl O atoms of neighbouring 1,3-pdta groups and three water molecules. The crystal structure is stabilized by intermolecular hydrogen bonding involving the water O—H group as donor and the carboxyl O atom as acceptor.

Keywords: crystal structure; propane-1,3-diyldinitrilotetraacetate; silver cation; chromate(III) complex; twist-boat conformer.

CCDC reference: 1424813

1. Chemical context

The hexadentate ligand, propane-1,3-diyldinitrilotetraacetate (abbreviated here as 1,3-pdta, C₁₁H₁₄N₂O₈) has been used for the preparation of complexes with many transition metal ions (Herak et al., 1984 ; Yamamoto et al., 1988 ; Douglas & Radanović, 1993 ). In the complex anion, [M(1,3-pdta)]^n-, the six-membered propane-1,3-diamine ring is referred to as the T ring, the equatorially coordinated glycinate ring as the G ring, and the axially coordinated glycinate ring as the R ring (see Scheme). The counter-ion and metal-center oxidation state play a very important role in conformational isomerism. Upon coordination of 1,3-pdta by a metal center, the six-membered T ring can take twist-boat or half-chair conformers (Meier et al., 2007 ). The twist-boat conformer was found in the crystal structures of K[Co(1,3-pdta)]·2H₂O (Nagao et al., 1972 ), Li[Fe(1,3-pdta)]·3H₂O (Yamamoto et al., 1988) and Na[Cr(1,3-pdta)]·3H₂O (Herak et al., 1984), whereas the half-chair form was observed in structural studies of [C(NH₂)₃][Fe(1,3-pdta)]·2H₂O (Meier et al., 2007) and Li₂[Co(1,3-pdta)]·3H₂O (Rychlewska et al., 2008 ). The crystal structure of Na[Cr(1,3-pdta)]·3H₂O (Herak et al., 1984) has also been reported previously. In this communication, we report the crystal structure of Ag[Cr(1,3-pdta)]·3H₂O in order to clarify unambiguously the bonding mode and the conformational geometry adopted by the Ag⁺ salt.

2. Structural commentary

This is another example of a [Cr(1,3-pdta)]⁻ anion but with a different cation. The crystal structure of the title compound is isotypic with Na[M(1,3-pdta)]·3H₂O (M = Fe, Cr or Rh; Okamoto et al., 1990 ; Herak et al., 1984) but it belongs to the orthorhombic space group P2₁2₁2₁ compared with the monoclinic space group P2₁/n of Li[Fe(1,3-pdta)]·3H₂O (Yamamoto et al., 1988) and orthorhombic space group B22₁2 of K[Co(1,3-pdta)]·2H₂O (Nagao et al., 1972). The structural analysis shows that the propane-1,3-diyldinitrilotetraacetate anion is coordinated octahedrally by the Cr metal center through four O and two N atoms. An ellipsoid plot of title complex showing the atomic numbering is given in Fig. 1. The Cr—O bond distances differ slightly, the mean equatorial and axial distances being 1.9672 (15) and 1.9544 (15) Å, respectively. The cis angles at the Cr^III ion range from 81.66 (6) to 99.41 (6)° and the trans angles are 173.07 (7), 175.01 (6) and 176.04 (7)°. The six-membered propane-1,3-diamine T ring (Fig. 1) adopts a flexible twist-boat conformation. The R rings are nearly planar and are in an envelope conformation. The G rings are much more puckered and are halfway between an envelope and a twist conformation. The Cr—O bond distances are greater in the G rings than in the R rings, and the average Cr—N bond length of 2.0727 (17) Å is 0.1119 Å longer than the average Cr—O bond distance. The Cr—N and Cr—O bond distances are in accordance with the values observed in Na[Cr(1,3-pdta)]·3H₂O. However, the average Ag—O distance of 2.525 (2) Å is slightly longer than the Na—O distance of 2.437 Å in Na[Cr(1,3-pdta)]·3H₂O (Herak et al., 1984).

Figure 1
The structures of the molecular entities in compound (I)

, showing the atom-numbering scheme. Non-H atoms are shown with displacement ellipsoids at the 50% probability level. [Symmetry codes: (i) −x + $[{1\over 2}]$ , −y + 1, z + $[{1\over 2}]$ ; (iii) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , 1 − z.]

3. Supramolecular features

The Ag⁺ cation is surrounded octahedrally by three water molecules (O9, O10 and O11) and three carboxylate O atoms [O6, O2ⁱⁱⁱ(x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , 1 − z) and O4ⁱ(−x + $[{1\over 2}]$ , −y + 1, z + $[{1\over 2}]$ )] that are not directly coordinated to the Cr atom (Fig. 1). Hydrogen bonds exist between the water molecules and the O atoms in the 1,3-pdta moiety (Table 1). An extensive array of these contacts generate a three-dimensional network of molecules stacked along the a-axis direction (Fig. 2). Non-coordinating and coordinating carboxylate O atoms take part in the formation of O—H⋯O hydrogen bonds, which contribute to the crystal packing stabilization and give rise to an infinite three-dimensional framework.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H1O1⋯O3ⁱ	0.84 (1)	1.95 (1)	2.797 (2)	178 (3)
O9—H2O1⋯O8ⁱⁱ	0.85 (1)	1.93 (1)	2.767 (3)	172 (4)
O10—H1O2⋯O5ⁱⁱⁱ	0.85 (1)	2.02 (1)	2.870 (2)	173 (4)
O10—H2O2⋯O2^iv	0.85 (1)	1.89 (1)	2.729 (3)	170 (4)
O11—H1O3⋯O7ⁱⁱ	0.84 (1)	2.33 (2)	3.142 (3)	163 (4)
O11—H2O3⋯O8^v	0.83 (1)	1.99 (2)	2.791 (3)	161 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iv) x+1, y, z; (v) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
Crystal packing of Ag[Cr(1,3-pdta)]·3H₂O, viewed perpendicular to the bc plane. Dashed lines represent O—H⋯O hydrogen-bonding interactions.

4. Database survey

A search of the Cambridge Structural Database (Version 5.38, May 2017 with three updates; Groom et al., 2016 ) gave just three hits for a related complex anion, the [Cr(C₁₁H₁₄N₂O₈)₂]⁻ unit. The crystal structure with an Na⁺ counter-cation (Herak et al., 1981 , 1984) has been determined. The crystal structures of Na[Cr(1,3-pndta)]·H₂O, K[Cr(1,3-pndta)]·H₂O and Ca[Cr(1,3-pndta)]₂·4H₂O (1,3-pndta = pentane-1,3-diyldinitrilotetraacetate; Warżajtis et al., 2014 ) have been reported previously. However, no structure of a [Cr(1,3-pdta)]⁻ or [Cr(1,3-pndta)]⁻ complex with Ag⁺ cation was found.

5. Synthesis and physical measurements

All chemicals were reagent-grade materials and were used without further purification. The UV–Vis absorption spectrum was recorded with a Cary 5000 UV–Vis–NIR Spectrophotometer. The FT–IR spectrum was obtained from a KBr pellet with a JASCO 460 plus series FT–IR spectrometer. Analyses for C, H, N were performed on a Carlo Erba 1108 Elemental Vario EL analyser. The precursor salt, Na[Cr(1,3-pdta)]·3H₂O was prepared as described previously (Weyh & Hamm, 1968 ; Herak et al., 1984). The sodium salt (0.20 g) was dissolved in 15 mL of water at 323 K and added to 3 mL of water containing 0.5 g of AgNO₃. The resulting solution was filtered and left to stand at room temperature for several days to give purple block-shaped crystals of the silver salt, Ag[Cr(1,3-pdta)]·3H₂O suitable for X-ray structural analysis. Elemental analysis calculated for Ag[Cr(C₁₁H₁₄N₂O₈)]·3H₂O: C, 25.60; H, 3.91; N, 5.43%; found: C, 25.71; H, 3.23; N, 5.36%. UV–vis data (H₂O solution, nm): 201 (vs), 223 (vs), 245 (sh), 385 (s), 506 (s), 700 (w). IR spectrum (KBr, cm⁻¹) : 3447 (vs, br) (ν OH), 3232 (sh), 2977 (vs) and 2941 (s) (ν CH), 1643 (s, br) (ν_as COO), 1473 (s), 1428 (m), 1363 (vs) and 1327 (vs) (ν_s COO), 1271 (sh), 1222 (s), 1144 (s), 1099 (vs), 1061 (m), 1029 (s), 988 (s), 941 (vs), 916 (vs), 897 (m), 853 (vs), 746 (vs), 690 (m), 632 (w), 579 (m), 529 (s), 486 (s), 433 (s).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.97 Å with U_iso(H) = 1.2U_eq(C). O-bound H atoms were assigned based on a difference-Fourier map, and were refined with distance restraints of 0.88 (2) Å (using DFIX and DANG commands), and U_iso(H) = 1.2U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	Ag[Cr(C₁₁H₁₄N₂O₈)]·3H₂O
M_r	516.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	260
a, b, c (Å)	8.7800 (18), 11.443 (2), 16.573 (3)
V (Å³)	1665.1 (6)
Z	4
Radiation type	Synchrotron, λ = 0.610 Å
μ (mm⁻¹)	1.25
Crystal size (mm)	0.17 × 0.13 × 0.07

Data collection
Diffractometer	ADSC Q210 CCD area detector
Absorption correction	Empirical (using intensity measurements) (HKL3000sm SCALEPACK; Otwinowski & Minor, 1997 )
T_min, T_max	0.843, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14937, 4807, 4738
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.051, 1.07
No. of reflections	4807
No. of parameters	253
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.65
Absolute structure	Flack x determined using 2027 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.008 (6)
Computer programs: PAL BL2D-SMDC (Shin et al., 2016 ), HKL3000sm (Otwinowski & Minor, 1997), SHELXT2014 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), DIAMOND (Putz & Brandenburg, 2014 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1424813

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018001743/nk2244sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018001743/nk2244Isup2.hkl

checkCIF report

Computing details top

Data collection: PAL BL2D-SMDC (Shin et al., 2016); cell refinement: HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

Silver [(propane-1,3-diyldinitrilo-κ²N,N')tetraacetato-κ⁴O,O',O'',O''']chromate(III) top

Crystal data top

Ag[Cr(C₁₁H₁₄N₂O₈)]·3H₂O	D_x = 2.059 Mg m⁻³
M_r = 516.16	Synchrotron radiation, λ = 0.610 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 33074 reflections
a = 8.7800 (18) Å	θ = 0.4–33.7°
b = 11.443 (2) Å	µ = 1.25 mm⁻¹
c = 16.573 (3) Å	T = 260 K
V = 1665.1 (6) Å³	Block, purple
Z = 4	0.17 × 0.13 × 0.07 mm
F(000) = 1036

Data collection top

ADSC Q210 CCD area detector diffractometer	4738 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnet	R_int = 0.041
ω scan	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: empirical (using intensity measurements) (HKL3000sm Scalepack; Otwinowski & Minor, 1997)	h = −12→12
T_min = 0.843, T_max = 1.000	k = −16→16
14937 measured reflections	l = −23→23
4807 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.020	w = 1/[σ²(F_o²) + (0.0272P)² + 0.5713P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.051	(Δ/σ)_max = 0.002
S = 1.07	Δρ_max = 0.41 e Å⁻³
4807 reflections	Δρ_min = −0.65 e Å⁻³
253 parameters	Absolute structure: Flack x determined using 2027 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
9 restraints	Absolute structure parameter: −0.008 (6)

Special details top

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

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

	x	y	z	U_iso*/U_eq
Cr1	0.24189 (3)	0.37102 (2)	0.24502 (2)	0.00967 (6)
O1	0.12226 (18)	0.25175 (12)	0.30121 (9)	0.0175 (3)
O2	−0.0055 (2)	0.21547 (15)	0.41423 (11)	0.0251 (3)
O3	0.08051 (18)	0.39909 (14)	0.16628 (9)	0.0186 (3)
O4	−0.16003 (19)	0.45764 (18)	0.15293 (11)	0.0282 (4)
O5	0.40372 (17)	0.35453 (13)	0.32531 (9)	0.0177 (3)
O6	0.63816 (19)	0.40881 (18)	0.35973 (11)	0.0286 (4)
O7	0.35275 (18)	0.27005 (12)	0.16811 (9)	0.0184 (3)
O8	0.5114 (3)	0.27410 (18)	0.06396 (14)	0.0398 (5)
N1	0.11336 (19)	0.48076 (14)	0.31737 (10)	0.0116 (3)
N2	0.38257 (19)	0.50019 (14)	0.19855 (11)	0.0132 (3)
C1	0.0637 (2)	0.28284 (17)	0.36905 (12)	0.0150 (3)
C2	0.0876 (2)	0.41046 (17)	0.39202 (12)	0.0165 (3)
H21	−0.001299	0.439533	0.420408	0.020*
H22	0.174899	0.417403	0.427556	0.020*
C3	−0.0428 (2)	0.45009 (19)	0.19226 (12)	0.0163 (3)
C4	−0.0348 (2)	0.50289 (17)	0.27589 (13)	0.0155 (3)
H41	−0.050662	0.586572	0.271860	0.019*
H42	−0.116537	0.470866	0.308456	0.019*
C5	0.5249 (2)	0.41833 (17)	0.31713 (12)	0.0159 (3)
C6	0.5206 (2)	0.50999 (17)	0.25100 (15)	0.0177 (3)
H61	0.522708	0.587001	0.275442	0.021*
H62	0.611006	0.502164	0.217770	0.021*
C7	0.4341 (3)	0.32390 (19)	0.11558 (13)	0.0192 (4)
C8	0.4251 (3)	0.45637 (18)	0.11673 (13)	0.0204 (4)
H81	0.522910	0.488802	0.101292	0.024*
H82	0.349954	0.482279	0.077731	0.024*
C9	0.1955 (2)	0.59037 (17)	0.33877 (13)	0.0183 (4)
H91	0.286801	0.569504	0.368393	0.022*
H92	0.131325	0.635424	0.374865	0.022*
C10	0.2416 (3)	0.66904 (17)	0.26797 (15)	0.0214 (4)
H10	0.153858	0.716501	0.254216	0.026*
H10B	0.319794	0.721905	0.287443	0.026*
C11	0.3006 (2)	0.61414 (17)	0.18957 (14)	0.0189 (4)
H11	0.214770	0.602452	0.153619	0.023*
H11B	0.368853	0.669379	0.163804	0.023*
Ag1	0.66176 (2)	0.43997 (2)	0.51158 (2)	0.02983 (6)
O9	0.4276 (2)	0.55599 (18)	0.50044 (10)	0.0323 (4)
H1O1	0.426 (5)	0.571 (3)	0.5503 (8)	0.039*
H2O1	0.455 (4)	0.6206 (19)	0.4800 (19)	0.039*
O10	0.8668 (3)	0.31407 (19)	0.54800 (12)	0.0345 (4)
H1O2	0.869 (5)	0.264 (3)	0.5862 (15)	0.041*
H2O2	0.899 (4)	0.276 (3)	0.5075 (14)	0.041*
O11	0.8203 (3)	0.60117 (17)	0.44997 (13)	0.0333 (4)
H1O3	0.758 (4)	0.637 (3)	0.421 (2)	0.040*
H2O3	0.853 (4)	0.649 (3)	0.4838 (18)	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.00884 (12)	0.01014 (11)	0.01002 (11)	−0.00089 (9)	0.00008 (9)	0.00054 (9)
O1	0.0211 (7)	0.0136 (6)	0.0177 (6)	−0.0061 (5)	0.0050 (5)	−0.0013 (5)
O2	0.0265 (8)	0.0234 (7)	0.0253 (8)	−0.0017 (6)	0.0088 (7)	0.0093 (6)
O3	0.0137 (6)	0.0295 (7)	0.0127 (6)	0.0031 (5)	−0.0030 (5)	−0.0026 (5)
O4	0.0137 (6)	0.0496 (10)	0.0212 (7)	0.0015 (7)	−0.0065 (6)	0.0017 (7)
O5	0.0133 (6)	0.0219 (7)	0.0180 (6)	−0.0021 (5)	−0.0042 (5)	0.0052 (5)
O6	0.0154 (7)	0.0474 (10)	0.0230 (8)	−0.0030 (6)	−0.0080 (6)	0.0007 (7)
O7	0.0211 (7)	0.0143 (6)	0.0199 (7)	0.0007 (5)	0.0072 (6)	−0.0012 (5)
O8	0.0520 (13)	0.0286 (9)	0.0388 (11)	−0.0050 (9)	0.0299 (10)	−0.0106 (8)
N1	0.0116 (6)	0.0113 (6)	0.0119 (6)	−0.0005 (5)	−0.0009 (5)	−0.0003 (5)
N2	0.0117 (7)	0.0118 (7)	0.0160 (7)	−0.0009 (5)	0.0001 (5)	0.0022 (5)
C1	0.0140 (8)	0.0163 (8)	0.0147 (8)	−0.0005 (6)	0.0008 (6)	0.0039 (6)
C2	0.0206 (9)	0.0182 (8)	0.0108 (7)	0.0008 (7)	0.0019 (7)	0.0011 (6)
C3	0.0114 (8)	0.0233 (8)	0.0144 (8)	−0.0021 (7)	−0.0017 (6)	0.0044 (7)
C4	0.0110 (7)	0.0192 (9)	0.0163 (8)	0.0017 (6)	−0.0018 (6)	0.0003 (6)
C5	0.0110 (7)	0.0210 (8)	0.0157 (8)	−0.0002 (6)	−0.0018 (6)	−0.0034 (7)
C6	0.0108 (7)	0.0167 (7)	0.0258 (9)	−0.0031 (6)	−0.0016 (7)	0.0007 (7)
C7	0.0201 (9)	0.0205 (8)	0.0169 (9)	−0.0021 (7)	0.0049 (7)	−0.0025 (7)
C8	0.0253 (10)	0.0191 (9)	0.0167 (8)	−0.0036 (7)	0.0074 (8)	0.0019 (7)
C9	0.0203 (9)	0.0147 (7)	0.0200 (9)	−0.0028 (6)	−0.0008 (7)	−0.0056 (6)
C10	0.0201 (9)	0.0121 (7)	0.0319 (10)	−0.0014 (7)	0.0024 (8)	0.0002 (7)
C11	0.0215 (9)	0.0121 (8)	0.0230 (9)	0.0017 (6)	0.0009 (7)	0.0052 (7)
Ag1	0.03046 (10)	0.03290 (9)	0.02614 (9)	0.00309 (7)	0.00069 (7)	0.00446 (7)
O9	0.0440 (10)	0.0339 (8)	0.0191 (8)	−0.0016 (8)	−0.0045 (7)	0.0039 (7)
O10	0.0401 (11)	0.0378 (10)	0.0257 (9)	0.0108 (8)	0.0103 (8)	0.0094 (7)
O11	0.0376 (10)	0.0302 (8)	0.0320 (9)	0.0014 (8)	−0.0099 (8)	−0.0045 (7)

Geometric parameters (Å, º) top

Cr1—O3	1.9530 (15)	C4—H41	0.9700
Cr1—O5	1.9558 (15)	C4—H42	0.9700
Cr1—O1	1.9578 (14)	C5—C6	1.517 (3)
Cr1—O7	1.9766 (15)	C6—H61	0.9700
Cr1—N1	2.0708 (17)	C6—H62	0.9700
Cr1—N2	2.0745 (16)	C7—C8	1.518 (3)
O1—C1	1.287 (2)	C8—H81	0.9700
O2—C1	1.234 (2)	C8—H82	0.9700
O3—C3	1.303 (2)	C9—C10	1.533 (3)
O4—C3	1.222 (2)	C9—H91	0.9700
O5—C5	1.298 (2)	C9—H92	0.9700
O6—C5	1.224 (3)	C10—C11	1.533 (3)
O6—Ag1	2.5501 (19)	C10—H10	0.9700
O7—C7	1.284 (3)	C10—H10B	0.9700
O8—C7	1.232 (3)	C11—H11	0.9700
N1—C9	1.490 (2)	C11—H11B	0.9700
N1—C4	1.493 (2)	Ag1—O10	2.383 (2)
N1—C2	1.493 (2)	Ag1—O9	2.455 (2)
N2—C8	1.493 (3)	Ag1—O11	2.526 (2)
N2—C6	1.496 (3)	O9—H1O1	0.844 (13)
N2—C11	1.497 (3)	O9—H2O1	0.848 (13)
C1—C2	1.524 (3)	O10—H1O2	0.854 (13)
C2—H21	0.9700	O10—H2O2	0.847 (13)
C2—H22	0.9700	O11—H1O3	0.839 (13)
C3—C4	1.514 (3)	O11—H2O3	0.834 (13)

O3—Cr1—O5	176.04 (7)	O6—C5—C6	119.87 (19)
O3—Cr1—O1	92.48 (7)	O5—C5—C6	116.36 (17)
O5—Cr1—O1	89.94 (7)	N2—C6—C5	112.83 (16)
O3—Cr1—O7	91.29 (7)	N2—C6—H61	109.0
O5—Cr1—O7	91.41 (7)	C5—C6—H61	109.0
O1—Cr1—O7	99.41 (6)	N2—C6—H62	109.0
O3—Cr1—N1	83.79 (7)	C5—C6—H62	109.0
O5—Cr1—N1	93.47 (7)	H61—C6—H62	107.8
O1—Cr1—N1	81.66 (6)	O8—C7—O7	123.7 (2)
O7—Cr1—N1	175.01 (7)	O8—C7—C8	120.0 (2)
O3—Cr1—N2	93.82 (7)	O7—C7—C8	116.21 (18)
O5—Cr1—N2	83.61 (7)	N2—C8—C7	111.09 (16)
O1—Cr1—N2	173.07 (7)	N2—C8—H81	109.4
O7—Cr1—N2	83.33 (7)	C7—C8—H81	109.4
N1—Cr1—N2	96.16 (7)	N2—C8—H82	109.4
C1—O1—Cr1	115.94 (12)	C7—C8—H82	109.4
C3—O3—Cr1	117.10 (13)	H81—C8—H82	108.0
C5—O5—Cr1	118.06 (13)	N1—C9—C10	116.11 (17)
C5—O6—Ag1	128.51 (15)	N1—C9—H91	108.3
C7—O7—Cr1	115.52 (13)	C10—C9—H91	108.3
C9—N1—C4	112.86 (15)	N1—C9—H92	108.3
C9—N1—C2	109.26 (16)	C10—C9—H92	108.3
C4—N1—C2	109.93 (16)	H91—C9—H92	107.4
C9—N1—Cr1	112.63 (12)	C11—C10—C9	119.81 (16)
C4—N1—Cr1	108.12 (12)	C11—C10—H10	107.4
C2—N1—Cr1	103.64 (11)	C9—C10—H10	107.4
C8—N2—C6	110.51 (16)	C11—C10—H10B	107.4
C8—N2—C11	108.81 (16)	C9—C10—H10B	107.4
C6—N2—C11	112.46 (16)	H10—C10—H10B	106.9
C8—N2—Cr1	104.29 (12)	N2—C11—C10	115.79 (17)
C6—N2—Cr1	108.67 (12)	N2—C11—H11	108.3
C11—N2—Cr1	111.80 (12)	C10—C11—H11	108.3
O2—C1—O1	123.65 (19)	N2—C11—H11B	108.3
O2—C1—C2	120.98 (19)	C10—C11—H11B	108.3
O1—C1—C2	115.36 (16)	H11—C11—H11B	107.4
N1—C2—C1	109.28 (15)	O10—Ag1—O9	168.15 (6)
N1—C2—H21	109.8	O10—Ag1—O11	97.34 (7)
C1—C2—H21	109.8	O9—Ag1—O11	92.08 (7)
N1—C2—H22	109.8	O10—Ag1—O6	103.11 (7)
C1—C2—H22	109.8	O9—Ag1—O6	86.18 (6)
H21—C2—H22	108.3	O11—Ag1—O6	75.40 (6)
O4—C3—O3	123.7 (2)	Ag1—O9—H1O1	93 (3)
O4—C3—C4	119.96 (19)	Ag1—O9—H2O1	105 (3)
O3—C3—C4	116.29 (16)	H1O1—O9—H2O1	103 (3)
N1—C4—C3	113.23 (15)	Ag1—O10—H1O2	128 (3)
N1—C4—H41	108.9	Ag1—O10—H2O2	111 (3)
C3—C4—H41	108.9	H1O2—O10—H2O2	104 (3)
N1—C4—H42	108.9	Ag1—O11—H1O3	103 (3)
C3—C4—H42	108.9	Ag1—O11—H2O3	113 (3)
H41—C4—H42	107.7	H1O3—O11—H2O3	107 (3)
O6—C5—O5	123.8 (2)

Cr1—O1—C1—O2	−174.74 (17)	C11—N2—C6—C5	129.15 (18)
Cr1—O1—C1—C2	4.1 (2)	Cr1—N2—C6—C5	4.8 (2)
C9—N1—C2—C1	−157.68 (16)	O6—C5—C6—N2	173.04 (19)
C4—N1—C2—C1	77.96 (19)	O5—C5—C6—N2	−7.8 (3)
Cr1—N1—C2—C1	−37.41 (17)	Cr1—O7—C7—O8	179.2 (2)
O2—C1—C2—N1	−156.79 (19)	Cr1—O7—C7—C8	−3.9 (3)
O1—C1—C2—N1	24.3 (2)	C6—N2—C8—C7	84.3 (2)
Cr1—O3—C3—O4	−168.99 (18)	C11—N2—C8—C7	−151.72 (18)
Cr1—O3—C3—C4	11.7 (2)	Cr1—N2—C8—C7	−32.3 (2)
C9—N1—C4—C3	120.00 (18)	O8—C7—C8—N2	−157.0 (2)
C2—N1—C4—C3	−117.75 (18)	O7—C7—C8—N2	25.9 (3)
Cr1—N1—C4—C3	−5.26 (18)	C4—N1—C9—C10	−61.7 (2)
O4—C3—C4—N1	177.0 (2)	C2—N1—C9—C10	175.70 (17)
O3—C3—C4—N1	−3.6 (2)	Cr1—N1—C9—C10	61.1 (2)
Ag1—O6—C5—O5	−62.2 (3)	N1—C9—C10—C11	−39.4 (3)
Ag1—O6—C5—C6	117.0 (2)	C8—N2—C11—C10	177.20 (17)
Cr1—O5—C5—O6	−173.92 (17)	C6—N2—C11—C10	−60.0 (2)
Cr1—O5—C5—C6	6.9 (2)	Cr1—N2—C11—C10	62.6 (2)
C8—N2—C6—C5	−109.04 (19)	C9—C10—C11—N2	−30.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H1O1···O3ⁱ	0.84 (1)	1.95 (1)	2.797 (2)	178 (3)
O9—H2O1···O8ⁱⁱ	0.85 (1)	1.93 (1)	2.767 (3)	172 (4)
O10—H1O2···O5ⁱⁱⁱ	0.85 (1)	2.02 (1)	2.870 (2)	173 (4)
O10—H2O2···O2^iv	0.85 (1)	1.89 (1)	2.729 (3)	170 (4)
O11—H1O3···O7ⁱⁱ	0.84 (1)	2.33 (2)	3.142 (3)	163 (4)
O11—H2O3···O8^v	0.83 (1)	1.99 (2)	2.791 (3)	161 (3)

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, −z+1; (iv) x+1, y, z; (v) −x+3/2, −y+1, z+1/2.

Funding information

This work was supported by a Research Grant of Andong National University. The X-ray crystallography experiment at PLS-II BL2D-SMC beamline was supported in part by MSIT and POSTECH.

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