catena-Poly[[bis­(quinolin-8-amine-κ2N,N′)cadmium(II)]-μ-cyanido-κ2N:C-[dicyanidonickel(II)]-μ-cyanido-κ2C:N]

Khelfa, S.; Touil, M.; Setifi, Z.; Setifi, F.; Al-Douh, M.H.; Glidewell, C.

doi:10.1107/S241431462100568X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 6| June 2021| x210568

https://doi.org/10.1107/S241431462100568X

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catena-Poly[[bis(quinolin-8-amine-κ²N,N′)cadmium(II)]-μ-cyanido-κ²N:C-[dicyanidonickel(II)]-μ-cyanido-κ²C:N]

Selma Khelfa,^a,^b Marwa Touil,^a,^b Zouaoui Setifi,^c,^b ^* Fatima Setifi,^b Mohammed Hadi Al-Douh ^d ^* and Christopher Glidewell ^e

^aDépartement de Chimie, Faculté des Sciences, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^bLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^cDépartement de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^dChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen, and ^eSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
^*Correspondence e-mail: setifi_zouaoui@yahoo.fr, md_douh@yahoo.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 28 May 2021; accepted 1 June 2021; online 8 June 2021)

In the title compound, [CdNi(C₉H₈N₂)₂(CN)₄]_n, the Cd and Ni atoms both lie on centres of inversion in space group P2₁/c. The Cd atom is coordinated by two bidentate quinolin-8-amine ligands and by the N atoms of two cyano ligands, while the square planar Ni atom is coordinated by the C atoms of four cyano ligands. These units form a one-dimensional coordination polymer containing an (–NC—Ni—CN—Cd–)_n backbone, and the coordination polymer chains are linked into a three-dimensional array by a combination of N—H⋯N and C—H⋯N hydrogen bonds, augmented by a π–π stacking interaction.

Keywords: synthesis; crystal structure; coordination polymer; hydrogen bonding.

CCDC reference: 2087407

Structure description

Transition-metal coordination compounds in which cyano ligands play the main structure-forming role, so-called cyanocarbanion or cyanometallate complexes, have been the subject of interest for many years, because of their magnetic and luminescent properties (Sieklucka et al., 2011 ; Benmansour et al., 2007 , 2008 , 2009 , 2012 ; Setifi et al., 2009 ; Yuste et al., 2009 ; Lehchili et al., 2017 ) including, in particular, their spin-crossover behaviour (Benmansour et al., 2010 ; Setifi et al., 2013 , 2014 , Bartual-Murgui et al., 2013 ). In a continuation of our general study of this area, we now report the crystal and molecular structure of the title compound.

In the structure of the title compound, the Cd and Ni ions both lie on centres of inversion, selected for convenience as those at (0.5, 0.5, 0.5) and (0.5, 0.5, 0), respectively. The [Ni(CN)₄]²⁻ units adopts the usual square planar configuration, while the Cd centre is coordinated by two bidentate quinolin-8-amine units and by the N atoms of two cyano ligands. The structure thus consists of one-dimensional coordination polymer based on an (–NC—Ni—CN—Cd–)_n backbone and running parallel to [001]. In the reference chain [Cd{quinolin-8-amine)₂]²⁺ units centred at (0.5, 0.5, n + 0.5) alternate with [Ni(CN)₄]²⁻ units centred at (0.5, 0.5, n), where n represents an integer in each case (Fig. 1). There are two types of N—H⋯N hydrogen bond in the structure (Table 1). Those involving atom H8A lie within the coordination polymer chain, but those involving atom H8B link the chain along (0.5, 0.5, z) to those along (0.5, 0, z) and (0.5, 1, z), so forming a sheet of hydrogen-bonded chains lying parallel to (100) (Fig. 2). Sheets of this type are linked into a three-dimensional array by two types of direction-specific interactions, a C—H⋯N hydrogen bond (Table 1) and a π–π stacking interaction. The C—H⋯N hydrogen bond combines with the inversion symmetry at both metal centres to generate a chain running parallel to the [20 $[\overline{1}]$ ] direction (Fig. 3), which links the (100) sheets into a three-dimensional structure. In addition, the carbocyclic rings in the quinolin-8-amine ligands at (x, y, z) and (2 − x, 1 − y, 1 − z), which lie in adjacent (100) sheets, are strictly parallel with an interplanar spacing of 3.4070 (6) Å; the ring-centroid separation is 3.5856 (8) Å, with a ring-centroid offset of ca 1.117 (2) Å: the interactions between the two types of ring in these two ligands are similar (Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4A/C5–C8/C8A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8A⋯N12ⁱ	0.880 (18)	2.416 (18)	3.2815 (18)	167.8 (15)
N8—H8B⋯N12ⁱⁱ	0.867 (19)	2.286 (19)	3.1275 (17)	163.9 (17)
C3—H3⋯Cg1ⁱⁱⁱ	0.95	2.78	3.6266 (17)	149
C4—H4⋯N12^iv	0.95	2.58	3.443 (2)	151
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The coordination polymer formed by the title compound. For the sake of clarity many of the C atom labels have been omitted: the atoms marked with a, b, c, d or e are at the symmetry positions (1 − x, 1 − y, −z), (1 − x, 1 − y, 1 − z), (x, y, −1 + z), (x, y, 1 + z) and (1 − x, 1 − y, 2 − z), respectively,. Displacement ellipsoids are drawn at the 80% probability level.

Figure 2
A projection along [100] of part of the crystal structure showing the formation of a hydrogen-bonded sheet of polymer chains, lying parallel to (100). For the sake of clarity, the H atoms bonded to C atoms have been omitted.

Figure 3
Part of the crystal structure showing the formation of a hydrogen-bonded chain running parallel to the [20 $[\overline{1}]$ ] direction. For the sake of clarity, the H atoms not involved in the motif shown have been omitted.

Figure 4
Part of the crystal structure showing the π-stacking of quinolin-8-amine ligands. For the sake of clarity, the unit-cell outline and the H atoms have been omitted: the Cd atom marked with an asterisk (*) is at (1.5, 1/2, 1/2).

The structure of the title compound is very similar to that of the iron(II)–nickel analogue, whose structure has been studied at both 293 K and 120 K, where the iron adopts high-spin and low-spin configurations, respectively (Setifi et al., 2014). This structural similarity of the Cd^II and Fe^II compounds is somewhat unexpected in view of the different effective radii of these ions (Shannon & Prewitt, 1969 , 1970 ), reflected in the differences between the M—N (M = Cd or Fe) distances in the two compounds, typically around 0.30 Å for each type of bond, itself reflected in the difference between the a repeat vectors, 9.4264 (3) Å for M = Cd but only 9.0035 (5) Å for M = Fe at 120 K.

Synthesis and crystallization

A solution of quinolin-8-amine (0.288 g, 2 mmol) in ethanol (10 ml) was added dropwise with stirring at 323 K to a solution of Cd[Ni(CN)₄]·H₂O (0.293 g, 1 mmol) in water (10 ml). This mixture was stirred for 4 h at 323 K and then filtered. Slow evaporation of the filtrate over a period of one week, at ambient temperature and in the presence of air, gave crystals suitable for single-crystal X-ray diffraction.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[CdNi(C₉H₈N₂)₂(CN)₄]
M_r	563.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	170
a, b, c (Å)	9.4264 (3), 11.8622 (3), 9.8257 (3)
β (°)	101.088 (2)
V (Å³)	1078.18 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.89
Crystal size (mm)	0.15 × 0.11 × 0.07

Data collection
Diffractometer	Rigaku Oxford Diffraction Xcalibur, Eos, Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 )
T_min, T_max	0.668, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	22794, 4057, 3319
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.770

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.063, 1.07
No. of reflections	4057
No. of parameters	154
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.51
Computer programs: CrysAlis PRO (Rigaku OD, 2015), SHELXS86 (Sheldrick, 2015 ), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2087407

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431462100568X/bt4114sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462100568X/bt4114Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS86 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2020).

catena-Poly[[bis(quinolin-8-amine-κ²N,N')cadmium(II)]-µ-cyanido-κ²N:C-[dicyanidonickel(II)]-µ-cyanido-κ²C:N] top

Crystal data top

[CdNi(C₉H₈N₂)₂(CN)₄]	F(000) = 560
M_r = 563.53	D_x = 1.736 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4264 (3) Å	Cell parameters from 4057 reflections
b = 11.8622 (3) Å	θ = 2.8–33.2°
c = 9.8257 (3) Å	µ = 1.89 mm⁻¹
β = 101.088 (2)°	T = 170 K
V = 1078.18 (6) Å³	Block, pale yellow
Z = 2	0.15 × 0.11 × 0.07 mm

Data collection top

Rigaku Oxford Diffraction Xcalibur, Eos, Gemini diffractometer	4057 independent reflections
Radiation source: fine-focus sealed X-raytube	3319 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 33.2°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −14→12
T_min = 0.668, T_max = 0.885	k = −18→18
22794 measured reflections	l = −12→15

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0239P)² + 0.6589P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4057 reflections	Δρ_max = 0.55 e Å⁻³
154 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints

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
Cd1	0.5000	0.5000	0.5000	0.01846 (4)
N1	0.69972 (12)	0.60058 (9)	0.46816 (12)	0.0200 (2)
C2	0.69877 (16)	0.69047 (12)	0.38871 (16)	0.0259 (3)
H2	0.6118	0.7094	0.3266	0.031*
C3	0.82124 (18)	0.75965 (12)	0.39193 (18)	0.0286 (3)
H3	0.8173	0.8224	0.3312	0.034*
C4	0.94535 (17)	0.73487 (12)	0.48371 (16)	0.0246 (3)
H4	1.0286	0.7809	0.4878	0.029*
C4A	0.94994 (14)	0.64063 (11)	0.57272 (13)	0.0200 (2)
C5	1.07330 (15)	0.61251 (13)	0.67437 (15)	0.0252 (3)
H5	1.1583	0.6572	0.6842	0.030*
C6	1.06942 (16)	0.52108 (14)	0.75798 (16)	0.0275 (3)
H6	1.1505	0.5045	0.8288	0.033*
C7	0.94610 (15)	0.45098 (13)	0.74017 (14)	0.0239 (3)
H7	0.9465	0.3868	0.7981	0.029*
C8	0.82593 (14)	0.47349 (11)	0.64121 (13)	0.0181 (2)
C8A	0.82395 (13)	0.57249 (10)	0.55881 (12)	0.0172 (2)
N8	0.70170 (12)	0.40018 (9)	0.61705 (12)	0.0198 (2)
H8A	0.694 (2)	0.3681 (15)	0.6961 (19)	0.024*
H8B	0.713 (2)	0.3478 (16)	0.5586 (19)	0.024*
Ni1	0.5000	0.5000	0.0000	0.01665 (5)
C11	0.50450 (15)	0.44216 (11)	0.17628 (14)	0.0217 (2)
N11	0.50472 (15)	0.41011 (11)	0.28716 (13)	0.0272 (2)
C12	0.62164 (15)	0.38568 (12)	−0.03912 (14)	0.0219 (2)
N12	0.69773 (15)	0.31621 (11)	−0.06549 (14)	0.0292 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01554 (6)	0.02316 (7)	0.01642 (7)	−0.00368 (4)	0.00242 (4)	0.00056 (4)
N1	0.0186 (5)	0.0198 (5)	0.0214 (5)	−0.0013 (4)	0.0032 (4)	0.0026 (4)
C2	0.0242 (6)	0.0248 (6)	0.0282 (7)	−0.0007 (5)	0.0040 (5)	0.0077 (5)
C3	0.0302 (7)	0.0236 (6)	0.0329 (8)	−0.0038 (5)	0.0088 (6)	0.0078 (5)
C4	0.0241 (7)	0.0227 (6)	0.0287 (7)	−0.0071 (5)	0.0098 (5)	−0.0012 (5)
C4A	0.0184 (5)	0.0209 (5)	0.0214 (5)	−0.0029 (4)	0.0059 (4)	−0.0036 (5)
C5	0.0182 (6)	0.0307 (7)	0.0264 (6)	−0.0041 (5)	0.0032 (5)	−0.0058 (5)
C6	0.0196 (6)	0.0353 (7)	0.0250 (7)	−0.0001 (5)	−0.0023 (5)	−0.0013 (6)
C7	0.0240 (6)	0.0249 (6)	0.0217 (6)	0.0015 (5)	0.0015 (5)	0.0025 (5)
C8	0.0186 (5)	0.0188 (5)	0.0172 (5)	−0.0005 (4)	0.0044 (4)	−0.0011 (4)
C8A	0.0175 (5)	0.0175 (5)	0.0172 (5)	−0.0010 (4)	0.0045 (4)	−0.0012 (4)
N8	0.0223 (5)	0.0171 (5)	0.0202 (5)	−0.0020 (4)	0.0045 (4)	0.0005 (4)
Ni1	0.01888 (11)	0.01653 (10)	0.01467 (10)	0.00374 (8)	0.00356 (8)	−0.00017 (7)
C11	0.0235 (6)	0.0203 (5)	0.0213 (6)	0.0032 (5)	0.0041 (5)	−0.0022 (5)
N11	0.0343 (7)	0.0269 (6)	0.0205 (5)	0.0014 (5)	0.0056 (4)	−0.0007 (5)
C12	0.0244 (6)	0.0217 (6)	0.0196 (5)	0.0029 (5)	0.0040 (4)	0.0016 (5)
N12	0.0300 (6)	0.0264 (6)	0.0326 (6)	0.0073 (5)	0.0094 (5)	0.0018 (5)

Geometric parameters (Å, º) top

Cd1—N1	2.3005 (11)	C5—C6	1.365 (2)
Cd1—N1ⁱ	2.3005 (11)	C5—H5	0.9500
Cd1—N8	2.3449 (12)	C6—C7	1.412 (2)
Cd1—N8ⁱ	2.3449 (12)	C6—H6	0.9500
Cd1—N11ⁱ	2.3554 (13)	C7—C8	1.3698 (19)
Cd1—N11	2.3555 (13)	C7—H7	0.9500
N1—C2	1.3205 (17)	C8—C8A	1.4245 (18)
N1—C8A	1.3691 (17)	C8—N8	1.4412 (17)
C2—C3	1.412 (2)	N8—H8A	0.880 (19)
C2—H2	0.9500	N8—H8B	0.868 (19)
C3—C4	1.365 (2)	Ni1—C11	1.8559 (14)
C3—H3	0.9500	Ni1—C11ⁱⁱ	1.8560 (14)
C4—C4A	1.4149 (19)	Ni1—C12	1.8631 (13)
C4—H4	0.9500	Ni1—C12ⁱⁱ	1.8631 (13)
C4A—C5	1.4192 (19)	C11—N11	1.1536 (18)
C4A—C8A	1.4212 (17)	C12—N12	1.1542 (18)

N1—Cd1—N1ⁱ	180.0	C6—C5—C4A	119.80 (13)
N1—Cd1—N8	73.80 (4)	C6—C5—H5	120.1
N1ⁱ—Cd1—N8	106.20 (4)	C4A—C5—H5	120.1
N1—Cd1—N8ⁱ	106.20 (4)	C5—C6—C7	120.64 (14)
N1ⁱ—Cd1—N8ⁱ	73.80 (4)	C5—C6—H6	119.7
N8—Cd1—N8ⁱ	180.0	C7—C6—H6	119.7
N1—Cd1—N11ⁱ	92.38 (4)	C8—C7—C6	121.45 (14)
N1ⁱ—Cd1—N11ⁱ	87.62 (4)	C8—C7—H7	119.3
N8—Cd1—N11ⁱ	86.85 (4)	C6—C7—H7	119.3
N8ⁱ—Cd1—N11ⁱ	93.15 (4)	C7—C8—C8A	118.87 (12)
N1—Cd1—N11	87.62 (4)	C7—C8—N8	122.28 (12)
N1ⁱ—Cd1—N11	92.38 (4)	C8A—C8—N8	118.85 (11)
N8—Cd1—N11	93.15 (4)	N1—C8A—C4A	121.24 (11)
N8ⁱ—Cd1—N11	86.85 (4)	N1—C8A—C8	119.10 (11)
N11ⁱ—Cd1—N11	180.0	C4A—C8A—C8	119.66 (12)
C2—N1—C8A	119.26 (12)	C8—N8—Cd1	109.42 (8)
C2—N1—Cd1	125.91 (9)	C8—N8—H8A	108.3 (12)
C8A—N1—Cd1	113.91 (8)	Cd1—N8—H8A	117.2 (12)
N1—C2—C3	122.93 (14)	C8—N8—H8B	109.8 (12)
N1—C2—H2	118.5	Cd1—N8—H8B	103.4 (12)
C3—C2—H2	118.5	H8A—N8—H8B	108.4 (17)
C4—C3—C2	118.87 (13)	C11—Ni1—C11ⁱⁱ	180.0
C4—C3—H3	120.6	C11—Ni1—C12	91.08 (6)
C2—C3—H3	120.6	C11ⁱⁱ—Ni1—C12	88.92 (6)
C3—C4—C4A	119.94 (13)	C11—Ni1—C12ⁱⁱ	88.92 (6)
C3—C4—H4	120.0	C11ⁱⁱ—Ni1—C12ⁱⁱ	91.08 (6)
C4A—C4—H4	120.0	C12—Ni1—C12ⁱⁱ	180.0
C4—C4A—C5	122.97 (13)	N11—C11—Ni1	177.27 (13)
C4—C4A—C8A	117.66 (12)	C11—N11—Cd1	133.82 (11)
C5—C4A—C8A	119.37 (12)	N12—C12—Ni1	178.59 (13)

C8A—N1—C2—C3	0.4 (2)	Cd1—N1—C8A—C4A	−167.20 (9)
Cd1—N1—C2—C3	168.70 (12)	C2—N1—C8A—C8	−178.04 (12)
N1—C2—C3—C4	−1.9 (2)	Cd1—N1—C8A—C8	12.30 (14)
C2—C3—C4—C4A	0.5 (2)	C4—C4A—C8A—N1	−3.70 (18)
C3—C4—C4A—C5	−177.41 (14)	C5—C4A—C8A—N1	175.86 (12)
C3—C4—C4A—C8A	2.1 (2)	C4—C4A—C8A—C8	176.80 (12)
C4—C4A—C5—C6	179.15 (14)	C5—C4A—C8A—C8	−3.63 (18)
C8A—C4A—C5—C6	−0.4 (2)	C7—C8—C8A—N1	−174.40 (12)
C4A—C5—C6—C7	2.9 (2)	N8—C8—C8A—N1	5.93 (17)
C5—C6—C7—C8	−1.4 (2)	C7—C8—C8A—C4A	5.11 (18)
C6—C7—C8—C8A	−2.6 (2)	N8—C8—C8A—C4A	−174.57 (11)
C6—C7—C8—N8	177.03 (13)	C7—C8—N8—Cd1	160.34 (11)
C2—N1—C8A—C4A	2.46 (19)	C8A—C8—N8—Cd1	−20.00 (13)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4A/C5–C8/C8A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8A···N12ⁱⁱⁱ	0.880 (18)	2.416 (18)	3.2815 (18)	167.8 (15)
N8—H8B···N12^iv	0.867 (19)	2.286 (19)	3.1275 (17)	163.9 (17)
C3—H3···Cg1^v	0.95	2.78	3.6266 (17)	149
C4—H4···N12^vi	0.95	2.58	3.443 (2)	151

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

Acknowledgements

Author contributions are as follows. Conceptualization, ZS and MHAD; methodology, ZS and MHAD; investigation, SK and MT; writing (original draft), CG and ZS; writing (review and editing of the manuscript), CG, FS and ZS; visualization, ZS and FS; funding acquisition, ZS and MHAD; resources, FS; supervision, FS.

Funding information

FS gratefully acknowledges the Algerian MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique), the DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique), as well as the Université Ferhat Abbas Sétif 1 for financial support.

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