Bis[5-methyl-2,3-bis­(thio­phen-2-yl)quinoxaline-κN1](nitrato-κ2O,O′)silver(I)

Crundwell, G.; Ellis, K.M.

doi:10.1107/S2414314623002651

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 3| March 2023| x230265

https://doi.org/10.1107/S2414314623002651

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Bis[5-methyl-2,3-bis(thiophen-2-yl)quinoxaline-κN¹](nitrato-κ²O,O′)silver(I)

Guy Crundwell ^a ^* and Kristin M. Ellis ^a

^aDepartment of Chemistry & Biochemistry, Central Connecticut State University, 1619 Stanley Street, New Britain, CT 06053, USA
^*Correspondence e-mail: crundwellg@ccsu.edu

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 17 March 2023; accepted 20 March 2023; online 23 March 2023)

The crystal structure of the title silver(I) complex, [Ag(NO₃)(C₁₇H₁₂N₂S₂)₂], has monoclinic (C2/c) symmetry, with the silver(I) atom and the nitrate group sitting on a twofold rotation axis. The complex also exhibits a thienyl-ring flip disorder, which is common for unsubstituted thiophene rings.

Keywords: crystal structure; thienylquinoxaline; silver nitrate.

CCDC reference: 2250090

Structure description

The central silver(I) atom and the nitrate anion sit on a twofold rotation axis. The two thienyl rings make dihedral angles of 17.14 (9) and 77.55 (6)° with respect to the quinoxaline moiety. The latter thienyl ring also has a flip disorder of 64.7 (4)%, which is common for unsubstituted thienyl rings (Crundwell et al., 2003 ). The nitrate anion bonds to the silver via two O atoms. As seen with similar bis-dithienylquinoxaline silver nitrate complexes (Crundwell et al., 2014 ), the N—Ag—N angle is correlated to the nitrate anion bonding to the metal in a bidentate fashion (Table 1, Fig. 1).

Table 1
Selected geometric parameters (Å, °)

Ag1—O1	2.533 (2)	Ag1—N1	2.2619 (17)
Ag1—O1ⁱ	2.533 (2)	O1—N3	1.232 (3)
Ag1—N1ⁱ	2.2619 (17)	O2—N3	1.224 (4)

O1ⁱ—Ag1—O1	49.30 (9)	N1ⁱ—Ag1—O1ⁱ	103.14 (7)
N1ⁱ—Ag1—O1	109.40 (7)	N1—Ag1—O1	103.14 (7)
N1—Ag1—O1ⁱ	109.41 (7)	N1—Ag1—N1ⁱ	144.14 (9)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Only symmetry-independent atoms are labeled. H atoms and the minor occupied sites of the disordered thienyl ring are omitted.

Synthesis and crystallization

Crystals were grown by combining warmed methanolic solutions of AgNO₃ and 5-methyl-2,3-(dithiophen-2-yl)-quinoxaline in a 1:2 molar ratio. The combined solution was pipetted into test tubes, which were then placed into amber vials and loosely sealed until small colorless crystals were observed. Crystals were harvested and used immediately since the silver salts deteriorate in light within days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Positional restraints and displacement parameter constraints were used in order to refine the amount of flip disorder, which was 64.7 (4)% for one of the thienyl rings (C14–C17, S2).

Table 2
Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₁₇H₁₂N₂S₂)₂]
M_r	786.69
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.9246 (10), 8.9789 (4), 22.2776 (13)
β (°)	120.967 (7)
V (Å³)	3245.9 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.92
Crystal size (mm)	0.38 × 0.35 × 0.20

Data collection
Diffractometer	Xcalibur, Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]$ )
T_min, T_max	0.886, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11880, 5743, 3896
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.777

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.04
No. of reflections	5743
No. of parameters	228
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.46
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]$ ), CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ), and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 2250090

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002651/bt4136sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002651/bt4136Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Bis[5-methyl-2,3-bis(thiophen-2-yl)quinoxaline-κN¹](nitrato-κ²O,O')silver(I) top

Crystal data top

[Ag(NO₃)(C₁₇H₁₂N₂S₂)₂]	F(000) = 1592
M_r = 786.69	D_x = 1.610 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.9246 (10) Å	Cell parameters from 3173 reflections
b = 8.9789 (4) Å	θ = 4.5–31.7°
c = 22.2776 (13) Å	µ = 0.92 mm⁻¹
β = 120.967 (7)°	T = 293 K
V = 3245.9 (3) Å³	Block, colorless
Z = 4	0.38 × 0.35 × 0.20 mm

Data collection top

Xcalibur, Sapphire3 diffractometer	5743 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 16.1790 pixels mm^-1	θ_max = 33.5°, θ_min = 4.1°
ω scans	h = −25→28
Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009)	k = −13→9
T_min = 0.886, T_max = 1.000	l = −34→19
11880 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.044P)² + 0.9845P] where P = (F_o² + 2F_c²)/3
5743 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.32 e Å⁻³
30 restraints	Δρ_min = −0.46 e Å⁻³

Special details top

Experimental. Hydrogen atoms on sp² carbons were included in calculated positions with a C-H distance of 0.93 Å and were included in the refinement in riding motion approximation with U_iso = 1.2U_eq of the carrier atom and hydrogen atoms on sp³ carbons were included in calculated positions with a C-H distance of 0.96 Å and were included in the refinement in riding motion approximation with U_iso = 1.5U_eq of the carrier atom.

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.

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 > 2sigma(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	Occ. (<1)
Ag1	0.5000	0.28104 (3)	0.7500	0.05147 (10)
O1	0.47816 (15)	0.5374 (2)	0.78512 (12)	0.0785 (6)
O2	0.5000	0.7444 (4)	0.7500	0.0920 (11)
N1	0.37028 (10)	0.2035 (2)	0.67321 (9)	0.0397 (4)
N2	0.21614 (10)	0.0848 (2)	0.57801 (9)	0.0404 (4)
N3	0.5000	0.6080 (4)	0.7500	0.0537 (7)
C1	0.27757 (12)	0.0778 (2)	0.56570 (10)	0.0386 (4)
C2	0.35742 (12)	0.1362 (2)	0.61561 (10)	0.0378 (4)
C3	0.30625 (13)	0.2174 (2)	0.68498 (11)	0.0396 (4)
C4	0.31805 (15)	0.2932 (3)	0.74494 (12)	0.0517 (6)
H4	0.3686	0.3366	0.7761	0.062*
C5	0.25366 (16)	0.3015 (3)	0.75613 (13)	0.0531 (6)
H5	0.2608	0.3511	0.7955	0.064*
C6	0.17693 (15)	0.2370 (3)	0.70951 (13)	0.0467 (5)
H6	0.1348	0.2435	0.7192	0.056*
C7	0.16241 (12)	0.1645 (2)	0.64991 (11)	0.0406 (4)
C8	0.22894 (12)	0.1547 (2)	0.63735 (10)	0.0367 (4)
C9	0.08016 (14)	0.0988 (3)	0.59912 (13)	0.0571 (6)
H9A	0.0870	−0.0036	0.5906	0.086*
H9B	0.0558	0.1532	0.5559	0.086*
H9C	0.0449	0.1045	0.6182	0.086*
C10	0.25759 (13)	0.0051 (3)	0.49975 (11)	0.0431 (5)
C11	0.29678 (16)	0.0086 (3)	0.46086 (12)	0.0536 (6)
H11	0.3452	0.0600	0.4739	0.064*
C12	0.25216 (19)	−0.0774 (3)	0.39869 (14)	0.0667 (7)
H12	0.2688	−0.0887	0.3663	0.080*
C13	0.18427 (16)	−0.1403 (3)	0.39128 (13)	0.0619 (7)
H13	0.1490	−0.2000	0.3534	0.074*
S1	0.16912 (4)	−0.10019 (8)	0.45797 (3)	0.06093 (18)
C14	0.42926 (12)	0.1231 (2)	0.60653 (11)	0.0405 (4)	0.647 (4)
C15	0.4616 (7)	0.2282 (9)	0.5845 (7)	0.0562 (8)	0.647 (4)
H15	0.4423	0.3255	0.5739	0.067*	0.647 (4)
C16	0.529 (2)	0.173 (2)	0.579 (3)	0.0586 (11)	0.647 (4)
H16	0.5563	0.2273	0.5614	0.070*	0.647 (4)
C17	0.5493 (8)	0.0331 (15)	0.6030 (10)	0.061 (2)	0.647 (4)
H17	0.5946	−0.0181	0.6076	0.073*	0.647 (4)
S2	0.48188 (14)	−0.03878 (19)	0.62341 (13)	0.0742 (5)	0.647 (4)
C14B	0.42926 (12)	0.1231 (2)	0.60653 (11)	0.0405 (4)	0.353 (4)
C15B	0.4753 (11)	−0.0013 (15)	0.6156 (11)	0.0742 (5)	0.353 (4)
H15B	0.4699	−0.0908	0.6339	0.089*	0.353 (4)
C16B	0.5332 (17)	0.024 (3)	0.593 (2)	0.061 (2)	0.353 (4)
H16B	0.5654	−0.0503	0.5902	0.073*	0.353 (4)
C17B	0.536 (4)	0.167 (4)	0.577 (5)	0.0586 (11)	0.353 (4)
H17B	0.5746	0.2062	0.5680	0.070*	0.353 (4)
S2B	0.4599 (3)	0.2654 (4)	0.5764 (3)	0.0562 (8)	0.353 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03173 (12)	0.0712 (2)	0.04456 (14)	0.000	0.01473 (10)	0.000
O1	0.0970 (16)	0.0848 (14)	0.0859 (15)	0.0033 (12)	0.0700 (14)	0.0022 (11)
O2	0.093 (3)	0.061 (2)	0.092 (2)	0.000	0.026 (2)	0.000
N1	0.0327 (8)	0.0489 (10)	0.0362 (8)	−0.0001 (7)	0.0168 (7)	−0.0003 (7)
N2	0.0359 (8)	0.0433 (10)	0.0414 (9)	−0.0012 (7)	0.0195 (7)	−0.0022 (7)
N3	0.0424 (14)	0.065 (2)	0.0481 (15)	0.000	0.0195 (12)	0.000
C1	0.0357 (10)	0.0393 (11)	0.0386 (10)	0.0009 (8)	0.0175 (8)	0.0012 (8)
C2	0.0332 (9)	0.0411 (11)	0.0384 (10)	0.0015 (8)	0.0180 (8)	0.0027 (8)
C3	0.0347 (9)	0.0469 (11)	0.0375 (9)	−0.0015 (9)	0.0188 (8)	−0.0006 (9)
C4	0.0449 (12)	0.0678 (16)	0.0446 (11)	−0.0105 (11)	0.0246 (10)	−0.0127 (11)
C5	0.0558 (14)	0.0644 (16)	0.0489 (12)	−0.0041 (12)	0.0340 (11)	−0.0090 (11)
C6	0.0461 (12)	0.0529 (13)	0.0517 (12)	0.0041 (10)	0.0328 (11)	0.0064 (10)
C7	0.0357 (10)	0.0422 (11)	0.0454 (11)	0.0016 (8)	0.0219 (9)	0.0064 (9)
C8	0.0345 (9)	0.0369 (10)	0.0382 (9)	0.0015 (8)	0.0184 (8)	0.0040 (8)
C9	0.0414 (12)	0.0742 (17)	0.0593 (14)	−0.0112 (11)	0.0284 (11)	−0.0076 (13)
C10	0.0390 (10)	0.0451 (12)	0.0404 (10)	0.0034 (9)	0.0169 (9)	−0.0024 (8)
C11	0.0591 (14)	0.0626 (15)	0.0425 (12)	−0.0111 (12)	0.0287 (11)	−0.0110 (11)
C12	0.0739 (19)	0.0817 (19)	0.0456 (13)	0.0012 (15)	0.0314 (13)	−0.0095 (13)
C13	0.0509 (14)	0.0680 (17)	0.0461 (12)	0.0061 (13)	0.0102 (11)	−0.0152 (12)
S1	0.0405 (3)	0.0738 (4)	0.0590 (4)	−0.0038 (3)	0.0189 (3)	−0.0197 (3)
C14	0.0351 (10)	0.0472 (12)	0.0405 (10)	0.0025 (8)	0.0203 (8)	0.0002 (9)
C15	0.0572 (9)	0.043 (2)	0.0860 (17)	0.0055 (13)	0.0495 (10)	0.0135 (13)
C16	0.053 (5)	0.066 (2)	0.073 (3)	−0.0032 (16)	0.043 (3)	0.003 (3)
C17	0.043 (5)	0.068 (2)	0.081 (6)	0.014 (3)	0.038 (6)	0.005 (3)
S2	0.0757 (8)	0.0617 (11)	0.1139 (11)	0.0299 (7)	0.0693 (9)	0.0374 (8)
C14B	0.0351 (10)	0.0472 (12)	0.0405 (10)	0.0025 (8)	0.0203 (8)	0.0002 (9)
C15B	0.0757 (8)	0.0617 (11)	0.1139 (11)	0.0299 (7)	0.0693 (9)	0.0374 (8)
C16B	0.043 (5)	0.068 (2)	0.081 (6)	0.014 (3)	0.038 (6)	0.005 (3)
C17B	0.053 (5)	0.066 (2)	0.073 (3)	−0.0032 (16)	0.043 (3)	0.003 (3)
S2B	0.0572 (9)	0.043 (2)	0.0860 (17)	0.0055 (13)	0.0495 (10)	0.0135 (13)

Geometric parameters (Å, º) top

Ag1—O1	2.533 (2)	C9—H9B	0.9600
Ag1—O1ⁱ	2.533 (2)	C9—H9C	0.9600
Ag1—N1ⁱ	2.2619 (17)	C10—C11	1.401 (3)
Ag1—N1	2.2619 (17)	C10—S1	1.720 (2)
O1—N3	1.232 (3)	C11—H11	0.9300
O2—N3	1.224 (4)	C11—C12	1.423 (3)
N1—C2	1.323 (3)	C12—H12	0.9300
N1—C3	1.371 (3)	C12—C13	1.334 (4)
N2—C1	1.326 (3)	C13—H13	0.9300
N2—C8	1.367 (3)	C13—S1	1.690 (3)
N3—O1ⁱ	1.232 (3)	C14—C15	1.348 (8)
C1—C2	1.437 (3)	C14—S2	1.692 (2)
C1—C10	1.468 (3)	C15—H15	0.9300
C2—C14	1.479 (3)	C15—C16	1.437 (11)
C3—C4	1.411 (3)	C16—H16	0.9300
C3—C8	1.409 (3)	C16—C17	1.337 (9)
C4—H4	0.9300	C17—H17	0.9300
C4—C5	1.366 (3)	C17—S2	1.688 (10)
C5—H5	0.9300	C15B—H15B	0.9300
C5—C6	1.404 (4)	C15B—C16B	1.437 (16)
C6—H6	0.9300	C16B—H16B	0.9300
C6—C7	1.373 (3)	C16B—C17B	1.335 (14)
C7—C8	1.426 (3)	C17B—H17B	0.9300
C7—C9	1.496 (3)	C17B—S2B	1.679 (16)
C9—H9A	0.9600

O1ⁱ—Ag1—O1	49.30 (9)	C7—C9—H9B	109.5
N1ⁱ—Ag1—O1	109.40 (7)	C7—C9—H9C	109.5
N1—Ag1—O1ⁱ	109.41 (7)	H9A—C9—H9B	109.5
N1ⁱ—Ag1—O1ⁱ	103.14 (7)	H9A—C9—H9C	109.5
N1—Ag1—O1	103.14 (7)	H9B—C9—H9C	109.5
N1—Ag1—N1ⁱ	144.14 (9)	C1—C10—S1	117.63 (16)
N3—O1—Ag1	96.32 (18)	C11—C10—C1	131.5 (2)
C2—N1—Ag1	117.43 (13)	C11—C10—S1	110.81 (16)
C2—N1—C3	119.18 (17)	C10—C11—H11	124.7
C3—N1—Ag1	123.33 (13)	C10—C11—C12	110.6 (2)
C1—N2—C8	118.92 (17)	C12—C11—H11	124.7
O1ⁱ—N3—O1	118.1 (3)	C11—C12—H12	123.2
O2—N3—O1ⁱ	120.97 (17)	C13—C12—C11	113.7 (2)
O2—N3—O1	120.97 (17)	C13—C12—H12	123.2
N2—C1—C2	120.49 (18)	C12—C13—H13	123.5
N2—C1—C10	115.22 (18)	C12—C13—S1	112.9 (2)
C2—C1—C10	124.28 (18)	S1—C13—H13	123.5
N1—C2—C1	120.83 (18)	C13—S1—C10	91.99 (13)
N1—C2—C14	116.47 (17)	C2—C14—S2	121.03 (17)
C1—C2—C14	122.69 (18)	C15—C14—C2	128.1 (5)
N1—C3—C4	120.00 (19)	C15—C14—S2	110.9 (4)
N1—C3—C8	119.80 (18)	C14—C15—H15	123.8
C8—C3—C4	120.20 (19)	C14—C15—C16	112.3 (8)
C3—C4—H4	120.7	C16—C15—H15	123.8
C5—C4—C3	118.5 (2)	C15—C16—H16	124.0
C5—C4—H4	120.7	C17—C16—C15	112.0 (10)
C4—C5—H5	119.2	C17—C16—H16	124.0
C4—C5—C6	121.5 (2)	C16—C17—H17	124.2
C6—C5—H5	119.2	C16—C17—S2	111.6 (8)
C5—C6—H6	119.1	S2—C17—H17	124.2
C7—C6—C5	121.8 (2)	C17—S2—C14	93.0 (4)
C7—C6—H6	119.1	C16B—C15B—H15B	124.4
C6—C7—C8	117.46 (19)	C15B—C16B—H16B	123.7
C6—C7—C9	122.07 (19)	C17B—C16B—C15B	112.6 (18)
C8—C7—C9	120.47 (19)	C17B—C16B—H16B	123.7
N2—C8—C3	120.67 (17)	C16B—C17B—H17B	124.4
N2—C8—C7	118.87 (18)	C16B—C17B—S2B	111.1 (17)
C3—C8—C7	120.46 (18)	S2B—C17B—H17B	124.4
C7—C9—H9A	109.5

Ag1—O1—N3—O1ⁱ	−0.002 (2)	C2—C1—C10—C11	−19.4 (4)
Ag1—O1—N3—O2	180.000 (2)	C2—C1—C10—S1	163.24 (17)
Ag1—N1—C2—C1	177.25 (14)	C2—C14—C15—C16	−177 (2)
Ag1—N1—C2—C14	−1.9 (2)	C2—C14—S2—C17	−179.4 (7)
Ag1—N1—C3—C4	5.0 (3)	C3—N1—C2—C1	−0.1 (3)
Ag1—N1—C3—C8	−174.50 (14)	C3—N1—C2—C14	−179.20 (18)
O1ⁱ—Ag1—O1—N3	0.001 (2)	C3—C4—C5—C6	−0.1 (4)
O1ⁱ—Ag1—N1—C2	85.90 (16)	C4—C3—C8—N2	178.0 (2)
O1—Ag1—N1—C2	137.02 (15)	C4—C3—C8—C7	−1.3 (3)
O1ⁱ—Ag1—N1—C3	−96.90 (16)	C4—C5—C6—C7	−1.0 (4)
O1—Ag1—N1—C3	−45.79 (17)	C5—C6—C7—C8	1.0 (3)
N1ⁱ—Ag1—O1—N3	90.85 (13)	C5—C6—C7—C9	−178.4 (2)
N1—Ag1—O1—N3	−104.43 (13)	C6—C7—C8—N2	−179.2 (2)
N1ⁱ—Ag1—N1—C2	−68.10 (14)	C6—C7—C8—C3	0.2 (3)
N1ⁱ—Ag1—N1—C3	109.09 (16)	C8—N2—C1—C2	3.0 (3)
N1—C2—C14—C15	−79.2 (8)	C8—N2—C1—C10	−178.15 (18)
N1—C2—C14—S2	101.6 (2)	C8—C3—C4—C5	1.3 (4)
N1—C3—C4—C5	−178.2 (2)	C9—C7—C8—N2	0.3 (3)
N1—C3—C8—N2	−2.5 (3)	C9—C7—C8—C3	179.6 (2)
N1—C3—C8—C7	178.19 (19)	C10—C1—C2—N1	178.41 (19)
N2—C1—C2—N1	−2.9 (3)	C10—C1—C2—C14	−2.5 (3)
N2—C1—C2—C14	176.19 (19)	C10—C11—C12—C13	0.3 (4)
N2—C1—C10—C11	161.8 (2)	C11—C10—S1—C13	0.7 (2)
N2—C1—C10—S1	−15.5 (3)	C11—C12—C13—S1	0.2 (3)
C1—N2—C8—C3	−0.4 (3)	C12—C13—S1—C10	−0.5 (2)
C1—N2—C8—C7	178.89 (19)	S1—C10—C11—C12	−0.6 (3)
C1—C2—C14—C15	101.7 (8)	C14—C15—C16—C17	−5 (4)
C1—C2—C14—S2	−77.6 (3)	C15—C14—S2—C17	1.2 (9)
C1—C10—C11—C12	−178.1 (2)	C15—C16—C17—S2	6 (4)
C1—C10—S1—C13	178.55 (18)	C16—C17—S2—C14	−4 (3)
C2—N1—C3—C4	−177.9 (2)	S2—C14—C15—C16	2 (2)
C2—N1—C3—C8	2.6 (3)	C15B—C16B—C17B—S2B	−9 (7)

Symmetry code: (i) −x+1, y, −z+3/2.

Funding information

Funding for this research was provided by: CSU-AAUP Research Grant .

References

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