Bis(isonicotinamide-κN)silver(I) tri­fluoro­methane­sulfonate aceto­nitrile disolvate

Adrian, R.A.; Ibarra, S.J.; Arman, H.D.

doi:10.1107/S2414314621010737

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 10| October 2021| x211073

https://doi.org/10.1107/S2414314621010737

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Bis(isonicotinamide-κN)silver(I) trifluoromethanesulfonate acetonitrile disolvate

Rafael A. Adrian,^a ^* Sara J. Ibarra ^a and Hadi D. Arman ^b

^aDepartment of Chemistry and Biochemistry, University of the Incarnate Word, San Antonio Texas 78209, USA, and ^bDepartment of Chemistry, The University of Texas at San Antonio, San Antonio Texas 78249, USA
^*Correspondence e-mail: adrian@uiwtx.edu

Edited by I. Brito, University of Antofagasta, Chile (Received 14 September 2021; accepted 15 October 2021; online 21 October 2021)

The central Ag^I atom of the title salt, [Ag(INAM)₂](CF₃SO₃)·2CH₃CN, where INAM is isonicotinamide (C₆H₆N₂O), is twofold coordinated by the pyridine N atoms of two isonicotinamide ligands creating a slightly distorted linear molecular geometry. The formation of polymeric chains {[Ag(INAM)₂]⁺}_n, held together by discrete hydrogen bonds through the amide group of the INAM ligand leaves voids for non-coordinating acetonitrile molecules that interact the silver metal center via regium bonds.

Keywords: crystal structure; silver atom; isonicotinamide; trifluoromethanesulfonate ions; acetonitrile; polymeric structure.

CCDC reference: 2116012

Structure description

Silver(I) isonicotinamide complexes have been investigated for the ability to form coordination complexes with a variety of molecular geometries due to amide hydrogen-bond synthons in their structure (Aakeröy & Beatty, 1998 ; Aakeröy et al., 1998 ; Lian et al. 2007 ), luminescent properties (Yeşilel et al., 2012 ), and antibacterial activity (Abu-Youssef et al., 2007 ; Yu et al., 2020 ). Our research group interest currently lies in the synthesis of novel metal complexes with biological activity; as part of our research in this area, herein, we describe the synthesis and structure of the title silver(I) complex.

As depicted in Fig. 1, the asymmetric unit of the title compound shows the Ag^I ion in a distorted linear coordination environment defined by two N-bonded isonicotamide ligands. Two acetonitrile molecules and a trifluoromethanesulfonate ion complete the asymmetric unit; the acetonitrile molecules sit at opposite sides of the plane defined by N1—Ag1—N3 with the nitrile group facing the silver(I) metal center. All relevant bond lengths and angles involving the Ag atom are presented in Table 1. The angle N1—Ag1—N3 of 172.78 (7) is within the reported values (174.9, 180, and 171.1) in the comparable silver(I) isonicotinamide structures currently available in the CSD (version 5.42 with update May 2021; Aakeröy & Beatty, 1998; refcode NISNEI; Bhogala et al., 2004 ; refcode NABYOF; Abu-Youssef et al., 2007; refcode XECZUB01).

Table 1
Selected geometric parameters (Å, °)

Ag1—N3	2.162 (2)	Ag1—N1	2.162 (2)

N1—Ag1—N3	172.78 (7)	N2—C6—C3	117.3 (2)
N4—C12—C9	118.3 (2)

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level; H atoms are omitted for clarity.

Two types of hydrogen-bonding motifs are present in the crystal lattice, with numerical values collated in Table 2. In the crystal packing, molecules self-assemble into layers aligned along the a-axis direction (Fig. 2) via N—H⋯O interactions. The trifluoromethanesulfonate anions fill the void between the layers and interact with the isonicotinamide ligands through additional N—H⋯O interactions. The pyridyl rings of the isonicotinamide ligand show π–π stacking interactions with centroid-to-centroid (Cg⋯Cg) distances ranging from 3.7005 (13) to 3.8503 (14) Å, and offset distances ranging from 1.940 to 2.056 Å, respectively.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.88	2.06	2.898 (3)	160
N2—H2B⋯O3	0.88	2.09	2.939 (3)	162
N4—H4A⋯O1ⁱⁱ	0.88	2.05	2.927 (3)	171
N4—H4B⋯O5ⁱⁱⁱ	0.88	2.22	3.033 (3)	154
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2
Perspective view of the packing structure of the title complex along the crystallographic b axis; H atoms are omitted for clarity.

Two different supramolecular interactions involving the silver atom are also responsible for the observed crystal packing: an Ag⋯Ag interaction with a distance between silver atoms of 3.4258 (3) Å, comparable to other silver complexes found in the CSD database (Titov et al., 2018 ; refcode FINWOR; Titov et al., 2019 ; refcode PIRCUR); and regium bonds, between the nitrogen of the acetonitrile solvent molecules and the silver atom (Alkorta et al., 2020 ; Zierkiewicz et al., 2018 ), with lengths of 2.916 Å for Ag1—N5 and 2.955 Å for Ag1—N6. (Fig. 3)

Figure 3
Capped sticks representation of the title molecule showing hydrogen bonds interactions (violet), regium bonds (light blue), Ag⋯Ag interactions (light green), and π–π stacking interactions (red).

Synthesis and crystallization

Silver trifluoromethanesulfonate (0.200 g, 0.778 mmol) was added to an acetonitrile solution of isonicotinamide (0.190 g, 1.56 mmol) and stirred for 30 min. The resulting clear solution was used to grow crystals by vapor diffusion with diethyl ether at 278 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	[Ag(C₆H₆N₂O)₂](CF₃O₃S)·2C₂H₃N)
M_r	583.30
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	9.4566 (2), 11.0330 (3), 11.9848 (3)
α, β, γ (°)	114.000 (2), 103.9287 (19), 95.129 (2)
V (Å³)	1083.72 (5)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	9.00
Crystal size (mm)	0.27 × 0.10 × 0.07

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.544, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24470, 4387, 4211
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.072, 1.08
No. of reflections	4387
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.78
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2116012

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621010737/bx4019sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621010737/bx4019Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621010737/bx4019Isup3.mol

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Bis(isonicotinamide-κN)silver(I) trifluoromethanesulfonate acetonitrile disolvate top

Crystal data top

[Ag(C₆H₆N₂O)₂](CF₃O₃S)·2C₂H₃N)	Z = 2
M_r = 583.30	F(000) = 584
Triclinic, P1	D_x = 1.788 Mg m⁻³
a = 9.4566 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.0330 (3) Å	Cell parameters from 12499 reflections
c = 11.9848 (3) Å	θ = 4.2–76.2°
α = 114.000 (2)°	µ = 9.00 mm⁻¹
β = 103.9287 (19)°	T = 100 K
γ = 95.129 (2)°	Plate, clear colourless
V = 1083.72 (5) Å³	0.27 × 0.10 × 0.07 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	4387 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4211 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.044
Detector resolution: 10.0000 pixels mm^-1	θ_max = 76.5°, θ_min = 4.2°
ω scans	h = −10→11
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2019)	k = −13→13
T_min = 0.544, T_max = 1.000	l = −15→14
24470 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0394P)² + 0.7P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.002
4387 reflections	Δρ_max = 0.77 e Å⁻³
300 parameters	Δρ_min = −0.78 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
Ag1	0.33026 (2)	0.42666 (2)	0.38452 (2)	0.01913 (7)
S1	0.80813 (6)	0.92406 (6)	0.27008 (6)	0.01835 (13)
F1	0.59457 (16)	1.01941 (15)	0.16879 (15)	0.0272 (3)
F3	0.77762 (19)	1.00737 (17)	0.09034 (15)	0.0314 (4)
F2	0.80186 (19)	1.16528 (15)	0.27750 (16)	0.0353 (4)
O2	−0.13731 (19)	0.48669 (17)	0.77676 (16)	0.0195 (3)
O1	0.68870 (19)	0.28645 (17)	−0.09989 (16)	0.0209 (4)
O5	0.96843 (19)	0.96695 (17)	0.31236 (17)	0.0238 (4)
O3	0.7525 (2)	0.79175 (17)	0.16192 (18)	0.0263 (4)
N3	0.1996 (2)	0.40757 (19)	0.50408 (18)	0.0151 (4)
N1	0.4587 (2)	0.4184 (2)	0.25573 (18)	0.0156 (4)
O4	0.7400 (2)	0.9518 (2)	0.37019 (19)	0.0350 (5)
N2	0.7732 (2)	0.5144 (2)	−0.0006 (2)	0.0191 (4)
H2A	0.822879	0.511950	−0.054633	0.023*
H2B	0.774705	0.592520	0.062122	0.023*
N4	−0.1246 (2)	0.2695 (2)	0.73398 (19)	0.0184 (4)
H4A	−0.184009	0.264893	0.779082	0.022*
H4B	−0.088239	0.198602	0.695256	0.022*
N6	0.1601 (2)	0.1602 (2)	0.1866 (2)	0.0262 (5)
N5	0.4275 (3)	0.7251 (2)	0.5268 (2)	0.0325 (5)
C9	0.0129 (2)	0.3874 (2)	0.6467 (2)	0.0150 (4)
C3	0.6141 (2)	0.4105 (2)	0.0827 (2)	0.0149 (4)
C2	0.5905 (3)	0.5331 (2)	0.1669 (2)	0.0164 (5)
H2	0.627509	0.615873	0.166627	0.020*
C10	0.0835 (2)	0.5137 (2)	0.6652 (2)	0.0150 (4)
H10	0.068538	0.594775	0.726905	0.018*
C8	0.0393 (3)	0.2713 (2)	0.5556 (2)	0.0167 (5)
H8	−0.005429	0.183595	0.541580	0.020*
C11	0.1752 (3)	0.5196 (2)	0.5931 (2)	0.0157 (4)
H11	0.223022	0.606106	0.606713	0.019*
C12	−0.0895 (3)	0.3837 (2)	0.7243 (2)	0.0158 (4)
C5	0.4811 (3)	0.3005 (2)	0.1740 (2)	0.0174 (5)
H5	0.443286	0.219160	0.176380	0.021*
C6	0.6954 (3)	0.3993 (2)	−0.0140 (2)	0.0165 (5)
C1	0.5128 (3)	0.5324 (2)	0.2506 (2)	0.0171 (5)
H1	0.496800	0.616240	0.307082	0.021*
C4	0.5567 (3)	0.2924 (2)	0.0869 (2)	0.0165 (5)
H4	0.569408	0.206974	0.030278	0.020*
C7	0.1313 (3)	0.2857 (2)	0.4862 (2)	0.0166 (5)
H7	0.147119	0.206188	0.423132	0.020*
C16	0.0818 (3)	0.1753 (2)	0.1065 (2)	0.0220 (5)
C17	−0.0166 (3)	0.1959 (3)	0.0045 (3)	0.0261 (5)
H17A	−0.119652	0.152936	−0.012235	0.039*
H17B	0.012716	0.155320	−0.073582	0.039*
H17C	−0.009032	0.293417	0.030980	0.039*
C14	0.5027 (3)	0.8301 (3)	0.5709 (3)	0.0259 (6)
C13	0.7428 (3)	1.0349 (2)	0.1983 (2)	0.0213 (5)
C15	0.6018 (3)	0.9632 (3)	0.6278 (3)	0.0302 (6)
H15A	0.642520	0.973096	0.563323	0.036*
H15B	0.683648	0.971724	0.700319	0.036*
H15C	0.545821	1.034243	0.657809	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.02101 (11)	0.02377 (11)	0.01987 (11)	0.00738 (7)	0.01347 (7)	0.01206 (8)
S1	0.0220 (3)	0.0175 (3)	0.0209 (3)	0.0087 (2)	0.0108 (2)	0.0103 (2)
F1	0.0224 (7)	0.0293 (8)	0.0322 (8)	0.0106 (6)	0.0075 (6)	0.0153 (7)
F3	0.0405 (9)	0.0372 (9)	0.0328 (9)	0.0161 (7)	0.0204 (7)	0.0243 (7)
F2	0.0379 (9)	0.0142 (7)	0.0423 (10)	0.0057 (6)	0.0000 (8)	0.0083 (7)
O2	0.0237 (9)	0.0203 (8)	0.0220 (8)	0.0116 (7)	0.0139 (7)	0.0113 (7)
O1	0.0266 (9)	0.0191 (8)	0.0220 (9)	0.0069 (7)	0.0151 (7)	0.0093 (7)
O5	0.0220 (9)	0.0198 (8)	0.0302 (10)	0.0066 (7)	0.0069 (7)	0.0117 (7)
O3	0.0290 (10)	0.0154 (8)	0.0335 (10)	0.0036 (7)	0.0094 (8)	0.0100 (8)
N3	0.0163 (9)	0.0182 (9)	0.0141 (9)	0.0071 (7)	0.0076 (7)	0.0080 (8)
N1	0.0157 (9)	0.0194 (9)	0.0153 (9)	0.0062 (7)	0.0073 (8)	0.0092 (8)
O4	0.0402 (12)	0.0530 (13)	0.0336 (11)	0.0270 (10)	0.0243 (9)	0.0294 (10)
N2	0.0229 (10)	0.0198 (10)	0.0190 (10)	0.0041 (8)	0.0137 (8)	0.0089 (8)
N4	0.0220 (10)	0.0187 (10)	0.0229 (10)	0.0086 (8)	0.0154 (8)	0.0116 (8)
N6	0.0259 (11)	0.0295 (11)	0.0251 (11)	0.0045 (9)	0.0108 (9)	0.0125 (10)
N5	0.0456 (15)	0.0285 (13)	0.0290 (12)	0.0141 (11)	0.0177 (11)	0.0133 (10)
C9	0.0143 (11)	0.0192 (11)	0.0139 (11)	0.0049 (9)	0.0044 (9)	0.0093 (9)
C3	0.0132 (10)	0.0173 (11)	0.0165 (11)	0.0050 (8)	0.0047 (9)	0.0092 (9)
C2	0.0174 (11)	0.0175 (11)	0.0178 (11)	0.0058 (9)	0.0069 (9)	0.0098 (9)
C10	0.0163 (11)	0.0156 (10)	0.0135 (10)	0.0061 (8)	0.0054 (9)	0.0058 (9)
C8	0.0178 (11)	0.0167 (11)	0.0184 (11)	0.0047 (9)	0.0075 (9)	0.0091 (9)
C11	0.0161 (11)	0.0164 (11)	0.0164 (11)	0.0052 (8)	0.0053 (9)	0.0085 (9)
C12	0.0151 (11)	0.0198 (11)	0.0147 (11)	0.0057 (9)	0.0055 (9)	0.0088 (9)
C5	0.0175 (11)	0.0171 (11)	0.0200 (12)	0.0040 (9)	0.0074 (9)	0.0094 (9)
C6	0.0143 (10)	0.0207 (11)	0.0180 (11)	0.0068 (9)	0.0057 (9)	0.0107 (9)
C1	0.0184 (11)	0.0183 (11)	0.0174 (11)	0.0060 (9)	0.0072 (9)	0.0091 (9)
C4	0.0177 (11)	0.0169 (11)	0.0162 (11)	0.0054 (9)	0.0074 (9)	0.0070 (9)
C7	0.0201 (11)	0.0161 (11)	0.0158 (11)	0.0059 (9)	0.0082 (9)	0.0072 (9)
C16	0.0253 (13)	0.0204 (11)	0.0227 (13)	0.0038 (10)	0.0143 (11)	0.0081 (10)
C17	0.0293 (14)	0.0265 (13)	0.0261 (13)	0.0082 (11)	0.0116 (11)	0.0131 (11)
C14	0.0328 (14)	0.0335 (15)	0.0226 (13)	0.0188 (12)	0.0154 (11)	0.0170 (12)
C13	0.0243 (12)	0.0169 (11)	0.0247 (13)	0.0077 (9)	0.0091 (10)	0.0095 (10)
C15	0.0310 (15)	0.0315 (14)	0.0327 (15)	0.0113 (12)	0.0126 (12)	0.0162 (12)

Geometric parameters (Å, º) top

Ag1—N3	2.162 (2)	C9—C12	1.505 (3)
Ag1—N1	2.162 (2)	C3—C2	1.396 (3)
S1—O5	1.4442 (18)	C3—C6	1.510 (3)
S1—O3	1.4433 (18)	C3—C4	1.390 (3)
S1—O4	1.434 (2)	C2—H2	0.9500
S1—C13	1.831 (2)	C2—C1	1.380 (3)
F1—C13	1.337 (3)	C10—H10	0.9500
F3—C13	1.333 (3)	C10—C11	1.378 (3)
F2—C13	1.331 (3)	C8—H8	0.9500
O2—C12	1.240 (3)	C8—C7	1.380 (3)
O1—C6	1.235 (3)	C11—H11	0.9500
N3—C11	1.348 (3)	C5—H5	0.9500
N3—C7	1.347 (3)	C5—C4	1.380 (3)
N1—C5	1.346 (3)	C1—H1	0.9500
N1—C1	1.345 (3)	C4—H4	0.9500
N2—H2A	0.8800	C7—H7	0.9500
N2—H2B	0.8800	C16—C17	1.459 (4)
N2—C6	1.338 (3)	C17—H17A	0.9800
N4—H4A	0.8800	C17—H17B	0.9800
N4—H4B	0.8800	C17—H17C	0.9800
N4—C12	1.331 (3)	C14—C15	1.460 (4)
N6—C16	1.144 (3)	C15—H15A	0.9800
N5—C14	1.141 (4)	C15—H15B	0.9800
C9—C10	1.395 (3)	C15—H15C	0.9800
C9—C8	1.395 (3)

N1—Ag1—N3	172.78 (7)	O2—C12—C9	118.8 (2)
O5—S1—C13	103.79 (11)	N4—C12—C9	118.3 (2)
O3—S1—O5	113.68 (11)	N1—C5—H5	118.5
O3—S1—C13	101.70 (11)	N1—C5—C4	122.9 (2)
O4—S1—O5	115.49 (12)	C4—C5—H5	118.5
O4—S1—O3	116.01 (13)	O1—C6—N2	123.2 (2)
O4—S1—C13	103.62 (11)	O1—C6—C3	119.5 (2)
C11—N3—Ag1	119.93 (16)	N2—C6—C3	117.3 (2)
C7—N3—Ag1	121.89 (15)	N1—C1—C2	123.0 (2)
C7—N3—C11	118.0 (2)	N1—C1—H1	118.5
C5—N1—Ag1	122.04 (16)	C2—C1—H1	118.5
C1—N1—Ag1	120.28 (16)	C3—C4—H4	120.3
C1—N1—C5	117.6 (2)	C5—C4—C3	119.4 (2)
H2A—N2—H2B	120.0	C5—C4—H4	120.3
C6—N2—H2A	120.0	N3—C7—C8	122.9 (2)
C6—N2—H2B	120.0	N3—C7—H7	118.5
H4A—N4—H4B	120.0	C8—C7—H7	118.5
C12—N4—H4A	120.0	N6—C16—C17	179.3 (3)
C12—N4—H4B	120.0	C16—C17—H17A	109.5
C10—C9—C12	118.3 (2)	C16—C17—H17B	109.5
C8—C9—C10	118.2 (2)	C16—C17—H17C	109.5
C8—C9—C12	123.5 (2)	H17A—C17—H17B	109.5
C2—C3—C6	123.5 (2)	H17A—C17—H17C	109.5
C4—C3—C2	117.9 (2)	H17B—C17—H17C	109.5
C4—C3—C6	118.5 (2)	N5—C14—C15	178.8 (3)
C3—C2—H2	120.5	F1—C13—S1	110.99 (17)
C1—C2—C3	119.1 (2)	F3—C13—S1	111.58 (16)
C1—C2—H2	120.5	F3—C13—F1	107.2 (2)
C9—C10—H10	120.3	F2—C13—S1	111.75 (17)
C11—C10—C9	119.4 (2)	F2—C13—F1	107.49 (19)
C11—C10—H10	120.3	F2—C13—F3	107.6 (2)
C9—C8—H8	120.5	C14—C15—H15A	109.5
C7—C8—C9	118.9 (2)	C14—C15—H15B	109.5
C7—C8—H8	120.5	C14—C15—H15C	109.5
N3—C11—C10	122.6 (2)	H15A—C15—H15B	109.5
N3—C11—H11	118.7	H15A—C15—H15C	109.5
C10—C11—H11	118.7	H15B—C15—H15C	109.5
O2—C12—N4	122.8 (2)

Ag1—N3—C11—C10	174.85 (16)	C2—C3—C4—C5	−0.8 (3)
Ag1—N3—C7—C8	−175.54 (17)	C10—C9—C8—C7	−1.2 (3)
Ag1—N1—C5—C4	176.85 (17)	C10—C9—C12—O2	17.8 (3)
Ag1—N1—C1—C2	−177.40 (17)	C10—C9—C12—N4	−162.0 (2)
O5—S1—C13—F1	−172.06 (16)	C8—C9—C10—C11	0.4 (3)
O5—S1—C13—F3	68.43 (19)	C8—C9—C12—O2	−161.1 (2)
O5—S1—C13—F2	−52.1 (2)	C8—C9—C12—N4	19.1 (3)
O3—S1—C13—F1	69.70 (18)	C11—N3—C7—C8	−0.6 (3)
O3—S1—C13—F3	−49.8 (2)	C12—C9—C10—C11	−178.5 (2)
O3—S1—C13—F2	−170.33 (18)	C12—C9—C8—C7	177.7 (2)
N1—C5—C4—C3	0.6 (3)	C5—N1—C1—C2	−0.7 (3)
O4—S1—C13—F1	−51.0 (2)	C6—C3—C2—C1	179.0 (2)
O4—S1—C13—F3	−170.54 (18)	C6—C3—C4—C5	−179.5 (2)
O4—S1—C13—F2	68.9 (2)	C1—N1—C5—C4	0.2 (3)
C9—C10—C11—N3	0.3 (3)	C4—C3—C2—C1	0.4 (3)
C9—C8—C7—N3	1.3 (3)	C4—C3—C6—O1	11.6 (3)
C3—C2—C1—N1	0.4 (3)	C4—C3—C6—N2	−167.8 (2)
C2—C3—C6—O1	−167.0 (2)	C7—N3—C11—C10	−0.2 (3)
C2—C3—C6—N2	13.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.88	2.06	2.898 (3)	160
N2—H2B···O3	0.88	2.09	2.939 (3)	162
N4—H4A···O1ⁱⁱ	0.88	2.05	2.927 (3)	171
N4—H4B···O5ⁱⁱⁱ	0.88	2.22	3.033 (3)	154

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

Acknowledgements

We are thankful for the support of the Department of Chemistry and Biochemistry at the University of the Incarnate Word and the X-ray Diffraction Laboratory at The University of Texas at San Antonio.

Funding information

Funding for this research was provided by: The Welch Foundation (award No. BN0032).

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