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In the title compound, [Ag(C16H14F2N2)2]NO3, the Ag atom, lying on a twofold rotation axis, is four-coordinated by N atoms from two symmetry-related bidentate ethyl­enedi­amine ligands. The AgN4 coordination forms a highly distorted tetrahedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004756/ci6199sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004756/ci6199Isup2.hkl
Contains datablock I

CCDC reference: 209879

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.040
  • wR factor = 0.114
  • Data-to-parameter ratio = 15.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 43.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The propensity for d10Ag+ cations to form coordination complexes with a variety of ligands, such as those containing N, O and S donors, has been widely studied (Buchholz et al., 1996; Amoroso et al., 1995; Michaelides et al., 1995). However, the isolation of silver(I) complexes is complicated by the fact that they often form polynuclear complexes. Moreover, from a practical viewpoint, there are serious problems, namely, nearly all polymeric silver(I) complexes are water insoluble and most of them are unstable upon exposure to light. In this work, a new organic bis-Schiff base ligand was utilized to ligate with silver(I) ions, to form a water soluble and stable complex, (I).

The title compound is an ionic complex of a bis[N,N'-bis(2-fluorobenzylidene)ethylenediamine]silver(I) cation and a nitrate anion. The asymmetric unit consists of one half of the cation and one half of the anion with the other halves generated by a crystallographic twofold axis. Atoms Ag1 and N3 lie on the twofold axis. The AgI atom is four-coordinated by two N atoms from each of the two symmetry-related bidentate N,N'-bis(2-fluorobenzylidene)ethylenediamine ligands. This AgN4 coordination forms a heavily distorted tetrahedral geometry, with bond angles around the Ag atom deviating significantly from ideal values (Table 1). The Ag—N bond lengths in (I) are slightly shorter compared with the mean value of 2.403 Å reported by Orpen et al. (1989), for such distances in the coordination complexes of Schiff bases.

Experimental top

At ambient temperature, an alcohol solution (5 ml) of diethylenetriamine (103 mg, 1 mmol) was added to 2-fluorobenzaldehyde (248 mg, 2 mmol) in alcohol (10 ml) with stirring. After half an hour, AgNO3 (170 mg, 1 mmol) in acetonitrile (5 ml) was added to the above solution. The resultant solution was kept in air to evaporate slowly. Colorless single crystals of the title complex, (I), were deposited and were collected by filtration. The crystals were washed with a mixture of alcohol and acetonitrile (1:1 v/v) and then dried in a vacuum desiccator over silica gel (yield 81%). Analysis calculated for (I), C32H26AgF4N4+·NO3-: C 53.95, H 3.68, N 9.83, F 10.67%; found: C 54.40, H 3.88, N 9.69, F 10.89%. IR spectra; 3010 (w), 1638 (m), 1610 (m), 1485 (m), 1452 (m), 1360 (w), 1347 (s), 1301 (m), 1282 (w), 1234 (m), 1198 (w), 1193 (w), 1101 (w), 1041 (w), 970 (w), 831 (w), 781 (w), 776 (m), 757 (s).

Refinement top

Atoms C8 and C9 of the ethylenediamine group were found to be disordered. The occupancies of the disordered positions C8A/C8B and C9A/C9B were refined to 0.55 (1)/0.45 (1). The corresponding N—C and C—C distances in the major and minor conformers were restrained to be equal. The N atom of the NO3- anion lies on a twofold axis and hence there are two positions for each O atom, related by the symmetry operation (1 - x, y, 1/2 - z), with equal occupancies. Significant deviation in the N—O bond lengths were observed and attempts to restrain them resulted in an unstable refinement. The H atoms were geometrically positioned and were treated as riding atoms on the parent C atoms, with C—H distances of 0.93 or 0.97 Å.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Only the major components of the disordered atoms are shown and for clarity, H atoms have been omitted.
Bis[N,N'-bis(2-fluorobenzylidene)ethylenediamine-κ2N,N']silver(I) nitrate top
Crystal data top
[Ag(C16H14F2N2)2]NO3F(000) = 1448
Mr = 714.46Dx = 1.564 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4783 reflections
a = 13.0142 (15) Åθ = 2.8–28.3°
b = 18.102 (2) ŵ = 0.73 mm1
c = 14.1367 (17) ÅT = 293 K
β = 114.328 (2)°Block, light yellow
V = 3034.6 (6) Å30.46 × 0.36 × 0.32 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
3699 independent reflections
Radiation source: fine-focus sealed tube2832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = 1713
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2317
Tmin = 0.730, Tmax = 0.800l = 1818
9317 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0551P)2 + 2.0621P]
where P = (Fo2 + 2Fc2)/3
3699 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.71 e Å3
7 restraintsΔρmin = 0.46 e Å3
Crystal data top
[Ag(C16H14F2N2)2]NO3V = 3034.6 (6) Å3
Mr = 714.46Z = 4
Monoclinic, C2/cMo Kα radiation
a = 13.0142 (15) ŵ = 0.73 mm1
b = 18.102 (2) ÅT = 293 K
c = 14.1367 (17) Å0.46 × 0.36 × 0.32 mm
β = 114.328 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
3699 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2832 reflections with I > 2σ(I)
Tmin = 0.730, Tmax = 0.800Rint = 0.022
9317 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0407 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.09Δρmax = 0.71 e Å3
3699 reflectionsΔρmin = 0.46 e Å3
237 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
xyzUiso*/UeqOcc. (<1)
Ag10.50000.128685 (17)0.25000.06565 (15)
N10.3355 (2)0.18904 (18)0.2193 (3)0.0980 (11)
N20.4202 (2)0.06010 (15)0.34250 (19)0.0669 (6)
F10.3222 (2)0.40612 (16)0.2132 (2)0.1119 (8)
F20.4300 (2)0.15841 (14)0.3706 (2)0.1054 (7)
C10.3644 (3)0.37560 (18)0.1489 (3)0.0719 (8)
C20.4100 (3)0.4209 (2)0.0990 (3)0.0844 (10)
H20.41260.47180.10920.101*
C30.4516 (3)0.3903 (2)0.0340 (3)0.0879 (11)
H30.48290.42020.00070.106*
C40.4474 (3)0.3151 (2)0.0198 (3)0.0815 (9)
H40.47520.29450.02530.098*
C50.4030 (3)0.27021 (18)0.0711 (2)0.0694 (8)
H50.40170.21940.06130.083*
C60.3596 (2)0.29996 (18)0.1381 (2)0.0631 (7)
C70.3077 (3)0.2547 (2)0.1921 (3)0.0902 (12)
H70.25100.27570.20730.108*
C8A0.2560 (4)0.1353 (3)0.2388 (5)0.064 (2)0.547 (12)
H8AA0.18860.16010.23550.077*0.547 (12)
H8AB0.23450.09500.18910.077*0.547 (12)
C9A0.3265 (6)0.1084 (6)0.3462 (5)0.069 (3)0.547 (12)
H9AA0.28040.08020.37240.083*0.547 (12)
H9AB0.35850.15000.39220.083*0.547 (12)
C8B0.3011 (8)0.1673 (4)0.3078 (7)0.084 (3)0.453 (12)
H8BA0.35550.18590.37390.101*0.453 (12)
H8BB0.22740.18740.29530.101*0.453 (12)
C9B0.2984 (5)0.0847 (4)0.3083 (12)0.080 (4)0.453 (12)
H9BA0.25210.06590.23960.096*0.453 (12)
H9BB0.26810.06690.35640.096*0.453 (12)
C100.4332 (2)0.00612 (19)0.3713 (2)0.0657 (7)
H100.37670.02860.38530.079*
C110.5328 (2)0.04975 (16)0.38402 (19)0.0577 (6)
C120.6366 (2)0.01855 (18)0.3989 (2)0.0651 (7)
H120.64440.03260.40140.078*
C130.7268 (3)0.0617 (2)0.4100 (3)0.0814 (9)
H130.79520.03970.42040.098*
C140.7173 (4)0.1373 (2)0.4058 (3)0.0869 (11)
H140.77920.16620.41280.104*
C150.6177 (3)0.1703 (2)0.3915 (3)0.0821 (10)
H150.61050.22140.38800.099*
C160.5289 (3)0.12610 (18)0.3824 (2)0.0696 (8)
N30.50000.6238 (2)0.25000.0816 (13)
O10.4437 (10)0.6235 (5)0.1510 (8)0.131 (3)0.50
O20.4918 (17)0.5708 (5)0.2910 (11)0.223 (7)0.50
O30.5121 (13)0.6788 (5)0.2925 (9)0.176 (6)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0617 (2)0.0581 (2)0.0970 (3)0.0000.05276 (19)0.000
N10.0704 (17)0.098 (2)0.152 (3)0.0307 (16)0.0726 (19)0.059 (2)
N20.0660 (14)0.0853 (17)0.0639 (14)0.0110 (12)0.0413 (12)0.0185 (13)
F10.1139 (18)0.1102 (18)0.1184 (18)0.0285 (15)0.0548 (15)0.0149 (15)
F20.0967 (16)0.0912 (14)0.1305 (19)0.0269 (13)0.0491 (14)0.0124 (14)
C10.0608 (17)0.076 (2)0.0694 (18)0.0178 (15)0.0175 (14)0.0011 (16)
C20.082 (2)0.0641 (19)0.099 (3)0.0027 (17)0.028 (2)0.0035 (18)
C30.082 (2)0.084 (2)0.095 (3)0.0050 (19)0.033 (2)0.020 (2)
C40.089 (2)0.088 (2)0.074 (2)0.0059 (19)0.0400 (18)0.0051 (18)
C50.0725 (18)0.0648 (17)0.0718 (18)0.0055 (14)0.0304 (15)0.0011 (14)
C60.0510 (14)0.0711 (18)0.0632 (16)0.0142 (13)0.0194 (12)0.0093 (14)
C70.071 (2)0.102 (3)0.117 (3)0.0379 (19)0.059 (2)0.043 (2)
C8A0.050 (3)0.085 (4)0.064 (4)0.003 (3)0.031 (3)0.002 (3)
C9A0.062 (4)0.104 (8)0.058 (4)0.010 (4)0.041 (3)0.013 (4)
C8B0.078 (5)0.078 (5)0.126 (9)0.016 (4)0.072 (6)0.022 (5)
C9B0.086 (7)0.071 (6)0.110 (11)0.004 (5)0.068 (7)0.014 (6)
C100.0622 (16)0.087 (2)0.0550 (15)0.0059 (14)0.0316 (13)0.0160 (14)
C110.0612 (15)0.0695 (17)0.0411 (12)0.0051 (12)0.0199 (11)0.0068 (12)
C120.0614 (16)0.0712 (18)0.0601 (16)0.0054 (14)0.0223 (13)0.0052 (14)
C130.0628 (18)0.098 (3)0.082 (2)0.0006 (18)0.0277 (16)0.0058 (19)
C140.089 (3)0.091 (3)0.087 (2)0.017 (2)0.043 (2)0.0075 (19)
C150.105 (3)0.067 (2)0.079 (2)0.0049 (19)0.043 (2)0.0025 (16)
C160.0755 (19)0.076 (2)0.0573 (16)0.0148 (16)0.0274 (14)0.0052 (14)
N30.073 (2)0.055 (3)0.132 (5)0.0000.058 (3)0.000
O10.165 (8)0.140 (9)0.106 (6)0.029 (6)0.076 (6)0.013 (5)
O20.343 (17)0.106 (6)0.25 (2)0.069 (10)0.155 (17)0.074 (9)
O30.229 (12)0.122 (6)0.227 (17)0.060 (9)0.145 (15)0.079 (8)
Geometric parameters (Å, º) top
Ag1—N1i2.280 (3)C8A—H8AB0.97
Ag1—N12.280 (3)C9A—H9AA0.97
Ag1—N2i2.334 (2)C9A—H9AB0.97
Ag1—N22.334 (2)C8B—C9B1.497 (7)
N1—C71.256 (4)C8B—H8BA0.97
N1—C8A1.526 (4)C8B—H8BB0.97
N1—C8B1.544 (5)C9B—H9BA0.97
N2—C101.255 (4)C9B—H9BB0.97
N2—C9A1.518 (4)C10—C111.465 (4)
N2—C9B1.521 (5)C10—H100.93
F1—C11.357 (4)C11—C161.383 (4)
F2—C161.360 (4)C11—C121.398 (4)
C1—C21.368 (5)C12—C131.364 (5)
C1—C61.376 (4)C12—H120.93
C2—C31.362 (6)C13—C141.373 (5)
C2—H20.93C13—H130.93
C3—C41.373 (5)C14—C151.364 (6)
C3—H30.93C14—H140.93
C4—C51.366 (5)C15—C161.368 (5)
C4—H40.93C15—H150.93
C5—C61.396 (4)N3—O31.140 (8)
C5—H50.93N3—O3i1.140 (8)
C6—C71.461 (5)N3—O21.148 (10)
C7—H70.93N3—O2i1.148 (10)
C8A—C9A1.495 (7)N3—O1i1.285 (10)
C8A—H8AA0.97N3—O11.285 (10)
N1i—Ag1—N1122.7 (2)C8A—C9A—H9AA110.0
N1i—Ag1—N2i76.24 (9)N2—C9A—H9AA110.0
N1—Ag1—N2i138.38 (12)C8A—C9A—H9AB110.0
N1i—Ag1—N2138.38 (12)N2—C9A—H9AB110.0
N1—Ag1—N276.24 (9)H9AA—C9A—H9AB108.4
N2i—Ag1—N2115.74 (13)C9B—C8B—N1105.8 (8)
C7—N1—C8A121.8 (3)C9B—C8B—H8BA110.6
C7—N1—C8B110.2 (4)N1—C8B—H8BA110.6
C7—N1—Ag1129.9 (2)C9B—C8B—H8BB110.6
C8A—N1—Ag1108.3 (3)N1—C8B—H8BB110.6
C8B—N1—Ag1106.7 (3)H8BA—C8B—H8BB108.7
C10—N2—C9A122.8 (5)C8B—C9B—N2105.7 (5)
C10—N2—C9B111.5 (4)C8B—C9B—H9BA110.6
C10—N2—Ag1131.2 (2)N2—C9B—H9BA110.6
C9A—N2—Ag1105.2 (4)C8B—C9B—H9BB110.6
C9B—N2—Ag1108.2 (5)N2—C9B—H9BB110.6
F1—C1—C2118.9 (3)H9BA—C9B—H9BB108.7
F1—C1—C6117.9 (3)N2—C10—C11123.3 (3)
C2—C1—C6123.3 (3)N2—C10—H10118.4
C3—C2—C1118.8 (3)C11—C10—H10118.4
C3—C2—H2120.6C16—C11—C12115.6 (3)
C1—C2—H2120.6C16—C11—C10120.8 (3)
C2—C3—C4120.0 (4)C12—C11—C10123.5 (3)
C2—C3—H3120.0C13—C12—C11121.2 (3)
C4—C3—H3120.0C13—C12—H12119.4
C5—C4—C3120.8 (4)C11—C12—H12119.4
C5—C4—H4119.6C12—C13—C14120.6 (4)
C3—C4—H4119.6C12—C13—H13119.7
C4—C5—C6120.6 (3)C14—C13—H13119.7
C4—C5—H5119.7C15—C14—C13120.4 (4)
C6—C5—H5119.7C15—C14—H14119.8
C1—C6—C5116.5 (3)C13—C14—H14119.8
C1—C6—C7120.6 (3)C14—C15—C16118.2 (3)
C5—C6—C7122.8 (3)C14—C15—H15120.9
N1—C7—C6123.6 (3)C16—C15—H15120.9
N1—C7—H7118.2F2—C16—C15118.7 (3)
C6—C7—H7118.2F2—C16—C11117.3 (3)
C9A—C8A—N1102.3 (6)C15—C16—C11124.0 (3)
C9A—C8A—H8AA111.3O3—N3—O2119.1 (9)
N1—C8A—H8AA111.3O3—N3—O1118.1 (11)
C9A—C8A—H8AB111.3O2—N3—O1114.6 (12)
N1—C8A—H8AB111.3O3i—N3—O2i119.1 (9)
H8AA—C8A—H8AB109.2O3i—N3—O1i118.1 (11)
C8A—C9A—N2108.6 (4)O2i—N3—O1i114.6 (12)
N1i—Ag1—N1—C718.3 (4)Ag1—N1—C7—C623.4 (7)
N2i—Ag1—N1—C789.0 (5)C1—C6—C7—N1151.8 (4)
N2—Ag1—N1—C7157.5 (5)C5—C6—C7—N130.3 (6)
N1i—Ag1—N1—C8A160.9 (3)C7—N1—C8A—C9A125.8 (5)
N2i—Ag1—N1—C8A91.7 (3)Ag1—N1—C8A—C9A53.5 (5)
N2—Ag1—N1—C8A21.7 (3)N1—C8A—C9A—N269.7 (8)
N1i—Ag1—N1—C8B117.8 (4)C10—N2—C9A—C8A121.2 (7)
N2i—Ag1—N1—C8B134.9 (4)C9B—N2—C9A—C8A51.3 (14)
N2—Ag1—N1—C8B21.5 (4)Ag1—N2—C9A—C8A49.3 (8)
N1i—Ag1—N2—C1080.0 (3)C7—N1—C8B—C9B160.2 (6)
N1—Ag1—N2—C10155.7 (3)Ag1—N1—C8B—C9B54.4 (7)
N2i—Ag1—N2—C1018.3 (3)N1—C8B—C9B—N267.5 (11)
N1i—Ag1—N2—C9A110.6 (4)C10—N2—C9B—C8B163.1 (7)
N1—Ag1—N2—C9A13.6 (4)C9A—N2—C9B—C8B41.1 (11)
N2i—Ag1—N2—C9A151.0 (4)Ag1—N2—C9B—C8B46.0 (11)
N1i—Ag1—N2—C9B136.9 (5)C9A—N2—C10—C11169.9 (4)
N1—Ag1—N2—C9B12.6 (5)C9B—N2—C10—C11164.6 (7)
N2i—Ag1—N2—C9B124.8 (5)Ag1—N2—C10—C1122.4 (5)
F1—C1—C2—C3179.6 (3)N2—C10—C11—C16158.7 (3)
C6—C1—C2—C30.9 (5)N2—C10—C11—C1221.6 (4)
C1—C2—C3—C40.1 (6)C16—C11—C12—C130.6 (4)
C2—C3—C4—C50.7 (6)C10—C11—C12—C13179.7 (3)
C3—C4—C5—C60.8 (5)C11—C12—C13—C140.5 (5)
F1—C1—C6—C5179.7 (3)C12—C13—C14—C150.6 (6)
C2—C1—C6—C50.8 (5)C13—C14—C15—C160.6 (6)
F1—C1—C6—C71.7 (4)C14—C15—C16—F2178.4 (3)
C2—C1—C6—C7178.8 (3)C14—C15—C16—C111.8 (5)
C4—C5—C6—C10.1 (4)C12—C11—C16—F2178.4 (3)
C4—C5—C6—C7177.9 (3)C10—C11—C16—F21.2 (4)
C8A—N1—C7—C6157.5 (4)C12—C11—C16—C151.8 (5)
C8B—N1—C7—C6158.3 (5)C10—C11—C16—C15178.5 (3)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Ag(C16H14F2N2)2]NO3
Mr714.46
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)13.0142 (15), 18.102 (2), 14.1367 (17)
β (°) 114.328 (2)
V3)3034.6 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.73
Crystal size (mm)0.46 × 0.36 × 0.32
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.730, 0.800
No. of measured, independent and
observed [I > 2σ(I)] reflections
9317, 3699, 2832
Rint0.022
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.114, 1.09
No. of reflections3699
No. of parameters237
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.71, 0.46

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
Ag1—N12.280 (3)N1—C71.256 (4)
Ag1—N22.334 (2)N2—C101.255 (4)
N1i—Ag1—N1122.7 (2)N1—Ag1—N276.24 (9)
N1i—Ag1—N2138.38 (12)N2i—Ag1—N2115.74 (13)
Symmetry code: (i) x+1, y, z+1/2.
 

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