13-Nitro­benzo[a][1,4]benzo­thia­zino[3,2-c]phenoxazine

Bader, M.M.; Fiester, C.; Pham, P.-T.T.; Bradely, A.; Nazzal, A.

doi:10.1107/S2414314624002992

organic compounds

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ISSN: 2414-3146

Volume 9| Part 4| April 2024| x240299

https://doi.org/10.1107/S2414314624002992

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13-Nitrobenzo[a][1,4]benzothiazino[3,2-c]phenoxazine

Mamoun M. Bader,^a ^* Cameron Fiester,^b Phuong-Truc T. Pham,^c Amy Bradely ^b and Amjad Nazzal ^d

^aDepartment of Chemistry, College of Science, Alfasial University, Riyadh 11533, Saudi Arabia, ^bDepartment of Chemistry, Wilkes University, Wilkes Barre, PA, USA, ^cDepartment of Chemistry, Pennsylvania State University, Scranton, PA 18512, USA, and ^dDepartment of Physics, Wilkes University, Wilkes Barre, PA, USA
^*Correspondence e-mail: mbader@alfaisal.edu

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 3 April 2024; accepted 7 April 2024; online 26 April 2024)

In the title compound, C₂₂H₁₁N₃O₃S, dihedral angle between the phenyl rings on the periphery of the molecule is 8.05 (18)°. In the crystal, aromatic π–π stacking distance and short C—H⋯O contacts are observed. The maximum absorption occurs at 688 nm.

Keywords: crystal structure; donor/acceptor; non centrosymmetric dye; fused heterocyclic; ladder oligomer.

CCDC reference: 2347503

Structure description

One area of interest in fused heterocyclic aromatic compounds is their potential to act as alternatives to oligoacenes for use in organic semiconducting devices (McLean et al., 1989 , 1990 ; Pham et al., 2008 ). Surprisingly, despite this intensely researched area, structural studies of these materials are scarce. Phenothiazine systems are readily obtained by reaction of halo-p-benzoquinones and amino thiophenols (Agarwal et al., 1980 ; Okafor et al., 1988 ; Spangler et al., 1989 ; Faleh et al., 2008 ) The title compound, C₂₂H₁₁N₃O₃S, is an asymmetric molecule with sulfur and oxygen bridging atoms (Fig. 1) that was prepared in two steps.

Figure 1
Structure of title compound.with displacement ellipsoids drawn at the 50% probability level.

The molecule is quasi-planar, as indicated by the torsion angles C8—C7—C22—N1 [−179.49 (19)°], S1—C7—C8—C15 [179.71 (16)°] and O2—N3—C11—C10 [−8.3 (3)°]. The nitro group subtends a dihedral angle of 8.0 (3)° with respect to its attached ring. A π–π-stacking distance of 3.290 (3) Å (Fig. 2) and close C—H⋯O interactions [H19⋯O2(1 − x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z) = 2.44, H12⋯O2( $[{1\over 4}]$ + x, $[{5\over 4}]$ − y, $[{1\over 4}]$ + z) = 2.50 and H3⋯O3( $[{3\over 4}]$ − x, $[{1\over 4}]$ + y, − $[{1\over 4}]$ + z) 2.63 Å] are observed.

Figure 2
Stacking of molecules with shortest observed distances (atom to atom).

A survey of the Cambridge Structural Database (Groom et al., 2016 ) on March 28, 2024 revealed no hits for this compound or any closely related structure. The closest is a structure from our group of the symmetrical molecule 15,16-dithia-5,10-diazanaphtho[2,3-a]benzo[c]anthracene, (Pham et al., 2008), which crystallizes in the monoclinic space group P2₁/c with four molecules in the unit cell. This molecule is also quasi-planar with dihedral angles between the three phenyl rings on the periphery of the molecule ranging from 1.89 to 6.65° and close C—H⋯S and C—H⋯N contacts. In comparison, no C—H⋯S or C—H⋯N close contacts are observed in the title compound.

Synthesis and crystallization

The target molecule was synthesized in a two-step process following published procedures (Agarwal et al., 1980; Okafor et al., 1988; Fiester et al., 2023 ; Spangler et al., 1989) as shown in Fig. 3.

Figure 3
Reaction scheme for the preparation of the title compound.

Synthesis of the precursor 6-chloro-9-nitro-5-oxo-5H-benzo[a]phenoxazine (1)

2-Amino-5-nitrophenol (5 mmol, 0.7612 g) and potassium acetate (5 mmol, 0.7740 g) were combined in 25 mL of ethanol. 2,3-Dichloro-1,4-napthophenol (5 mmol, 1.120 g) was added to the solution, which was then heated gently for 2 h. The solution was cooled and filtered, resulting in an orange–red solid (1.0028 g, 77%), m.p. 255°C.

Synthesis of the title compound 13-nitrobenzo[a][1,4]benzothiazino[3,2-c]phenoxazine

2-Aminothiophenol (excess) and potassium acetate were combined in 10 mL of ethanol. Precursor 1 (0.9781 g, 3.7 mmol) was added to the solution, which was then heated at 60°C for approximately 5 h. The solution was cooled and filtered, resulting in a dark-blue solid (0.4136 g, 33% yield), m.p. 340°C. The product was crystallized by slow evaporation from dichloromethane solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₂H₁₁N₃O₃S
M_r	397.40
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	130
a, b, c (Å)	6.7497 (9), 52.478 (7), 18.832 (3)
V (Å³)	6670.5 (16)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.13 × 0.05

Data collection
Diffractometer	Bruker PHOTON-III CPAD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.681, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	22321, 5093, 4718
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.087, 1.03
No. of reflections	5093
No. of parameters	262
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23
Absolute structure	Flack x determined using 2109 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.01 (3)
Computer programs: APEX4 and SAINT (Bruker, 2014 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 2347503

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624002992/nx4001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624002992/nx4001Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624002992/nx4001Isup3.cml

checkCIF report

Computing details top

13-Nitrobenzo[a][1,4]benzothiazino[3,2-c]phenoxazine top

Crystal data top

C₂₂H₁₁N₃O₃S	D_x = 1.583 Mg m⁻³
M_r = 397.40	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 2857 reflections
a = 6.7497 (9) Å	θ = 2.3–30.0°
b = 52.478 (7) Å	µ = 0.23 mm⁻¹
c = 18.832 (3) Å	T = 130 K
V = 6670.5 (16) Å³	Needle, brown
Z = 16	0.20 × 0.13 × 0.05 mm
F(000) = 3264

Data collection top

Bruker PHOTON-III CPAD diffractometer	4718 reflections with I > 2σ(I)
Radiation source: micro-focus	R_int = 0.034
φ and ω scans	θ_max = 30.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −6→9
T_min = 0.681, T_max = 0.746	k = −74→73
22321 measured reflections	l = −26→26
5093 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.087	(Δ/σ)_max = 0.003
S = 1.03	Δρ_max = 0.36 e Å⁻³
5093 reflections	Δρ_min = −0.23 e Å⁻³
262 parameters	Absolute structure: Flack x determined using 2109 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.01 (3)

Special details top

Experimental. Prof. M. Bader/C. Fiester

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
S1	0.51936 (8)	0.77762 (2)	0.36455 (3)	0.02344 (12)
O1	0.4662 (2)	0.73153 (2)	0.43558 (7)	0.0198 (3)
O2	0.3593 (2)	0.64760 (3)	0.32680 (8)	0.0293 (3)
O3	0.4057 (3)	0.62015 (3)	0.41134 (8)	0.0338 (4)
N1	0.5694 (3)	0.82016 (3)	0.48286 (9)	0.0227 (3)
N2	0.4745 (3)	0.72228 (3)	0.58474 (9)	0.0209 (3)
N3	0.3919 (3)	0.64213 (3)	0.38935 (9)	0.0225 (3)
C1	0.5695 (3)	0.81010 (4)	0.35380 (11)	0.0223 (4)
C2	0.5942 (3)	0.81878 (4)	0.28432 (12)	0.0273 (4)
H2	0.581985	0.807310	0.245538	0.033*
C3	0.6371 (3)	0.84436 (4)	0.27226 (13)	0.0312 (4)
H3	0.655028	0.850328	0.225073	0.037*
C4	0.6537 (3)	0.86123 (4)	0.32886 (13)	0.0306 (5)
H4	0.683467	0.878653	0.320257	0.037*
C5	0.6269 (3)	0.85268 (4)	0.39781 (13)	0.0271 (4)
H5	0.637067	0.864410	0.436066	0.033*
C6	0.5849 (3)	0.82691 (4)	0.41212 (11)	0.0227 (4)
C7	0.5201 (3)	0.77476 (3)	0.45674 (10)	0.0189 (3)
C8	0.4934 (3)	0.75094 (3)	0.48421 (10)	0.0180 (3)
C9	0.4496 (3)	0.70709 (3)	0.46210 (9)	0.0177 (3)
C10	0.4258 (3)	0.68769 (3)	0.41332 (9)	0.0181 (3)
H10	0.416843	0.691018	0.363837	0.022*
C11	0.4155 (3)	0.66298 (3)	0.44028 (10)	0.0198 (3)
C12	0.4311 (3)	0.65728 (4)	0.51177 (10)	0.0225 (4)
H12	0.429063	0.640118	0.527818	0.027*
C13	0.4499 (3)	0.67737 (4)	0.55959 (10)	0.0223 (4)
H13	0.457868	0.673908	0.609021	0.027*
C14	0.4573 (3)	0.70262 (4)	0.53568 (10)	0.0192 (4)
C15	0.4910 (3)	0.74534 (4)	0.55893 (10)	0.0184 (3)
C16	0.5132 (3)	0.76694 (4)	0.60727 (11)	0.0212 (4)
C17	0.5121 (3)	0.76263 (4)	0.68082 (11)	0.0283 (4)
H17	0.492764	0.745872	0.698569	0.034*
C18	0.5391 (4)	0.78256 (5)	0.72745 (12)	0.0370 (5)
H18	0.536487	0.779604	0.777212	0.044*
C19	0.5703 (4)	0.80725 (5)	0.70113 (12)	0.0355 (5)
H19	0.591278	0.820946	0.733259	0.043*
C20	0.5707 (4)	0.81181 (4)	0.62893 (11)	0.0280 (4)
H20	0.591466	0.828616	0.611690	0.034*
C21	0.5408 (3)	0.79174 (4)	0.58094 (10)	0.0214 (4)
C22	0.5444 (3)	0.79669 (4)	0.50355 (10)	0.0202 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0338 (3)	0.01553 (18)	0.02103 (19)	−0.00169 (18)	0.00096 (19)	0.00055 (17)
O1	0.0289 (7)	0.0131 (5)	0.0174 (6)	−0.0013 (5)	−0.0005 (5)	0.0009 (5)
O2	0.0431 (9)	0.0224 (7)	0.0225 (7)	−0.0040 (7)	−0.0027 (6)	−0.0007 (5)
O3	0.0555 (10)	0.0147 (6)	0.0313 (8)	−0.0026 (7)	0.0011 (7)	0.0011 (6)
N1	0.0214 (8)	0.0178 (7)	0.0289 (8)	0.0004 (6)	−0.0017 (7)	−0.0013 (6)
N2	0.0239 (8)	0.0210 (8)	0.0178 (7)	0.0016 (6)	−0.0014 (6)	0.0003 (6)
N3	0.0279 (9)	0.0159 (7)	0.0236 (7)	−0.0029 (6)	0.0024 (7)	−0.0003 (6)
C1	0.0208 (9)	0.0172 (8)	0.0289 (10)	−0.0003 (7)	−0.0003 (7)	0.0031 (7)
C2	0.0299 (10)	0.0229 (9)	0.0291 (10)	−0.0020 (8)	−0.0007 (8)	0.0042 (7)
C3	0.0312 (11)	0.0244 (9)	0.0380 (11)	−0.0032 (8)	−0.0025 (9)	0.0089 (8)
C4	0.0281 (11)	0.0201 (9)	0.0437 (12)	−0.0024 (8)	−0.0029 (9)	0.0073 (8)
C5	0.0230 (10)	0.0175 (8)	0.0409 (11)	0.0015 (7)	−0.0027 (8)	−0.0002 (8)
C6	0.0182 (8)	0.0175 (8)	0.0323 (10)	0.0002 (7)	−0.0011 (8)	0.0011 (7)
C7	0.0193 (9)	0.0164 (8)	0.0209 (8)	0.0007 (6)	−0.0008 (6)	−0.0012 (6)
C8	0.0185 (8)	0.0166 (8)	0.0190 (8)	0.0012 (6)	−0.0009 (6)	−0.0022 (6)
C9	0.0192 (8)	0.0147 (7)	0.0191 (8)	0.0010 (6)	−0.0004 (6)	0.0022 (6)
C10	0.0215 (8)	0.0145 (7)	0.0185 (7)	−0.0005 (6)	0.0001 (7)	0.0009 (6)
C11	0.0214 (9)	0.0154 (7)	0.0226 (8)	−0.0013 (7)	0.0007 (7)	−0.0011 (6)
C12	0.0276 (9)	0.0174 (8)	0.0223 (9)	0.0000 (7)	−0.0002 (7)	0.0030 (6)
C13	0.0277 (10)	0.0198 (9)	0.0193 (8)	0.0007 (7)	−0.0003 (7)	0.0030 (6)
C14	0.0202 (8)	0.0176 (8)	0.0198 (8)	0.0008 (6)	−0.0003 (6)	−0.0002 (6)
C15	0.0183 (8)	0.0177 (8)	0.0193 (8)	0.0017 (6)	−0.0015 (6)	−0.0005 (6)
C16	0.0218 (9)	0.0215 (8)	0.0202 (8)	0.0026 (7)	−0.0026 (7)	−0.0031 (7)
C17	0.0381 (11)	0.0242 (10)	0.0227 (9)	0.0014 (8)	−0.0020 (8)	−0.0032 (8)
C18	0.0572 (15)	0.0331 (11)	0.0208 (9)	0.0032 (11)	−0.0047 (10)	−0.0081 (9)
C19	0.0500 (14)	0.0286 (11)	0.0280 (10)	0.0029 (10)	−0.0051 (10)	−0.0108 (8)
C20	0.0322 (11)	0.0218 (9)	0.0302 (10)	0.0005 (8)	−0.0026 (8)	−0.0082 (8)
C21	0.0202 (9)	0.0198 (8)	0.0244 (9)	0.0032 (7)	−0.0022 (7)	−0.0049 (7)
C22	0.0178 (8)	0.0184 (8)	0.0242 (8)	0.0011 (6)	−0.0006 (6)	−0.0028 (6)

Geometric parameters (Å, º) top

S1—C7	1.743 (2)	C8—C15	1.437 (2)
S1—C1	1.750 (2)	C9—C10	1.381 (2)
O1—C9	1.381 (2)	C9—C14	1.407 (2)
O1—C8	1.382 (2)	C10—C11	1.395 (2)
O2—N3	1.232 (2)	C10—H10	0.9500
O3—N3	1.229 (2)	C11—C12	1.383 (3)
N1—C22	1.303 (3)	C12—C13	1.392 (3)
N1—C6	1.382 (3)	C12—H12	0.9500
N2—C15	1.309 (2)	C13—C14	1.400 (3)
N2—C14	1.390 (2)	C13—H13	0.9500
N3—C11	1.464 (2)	C15—C16	1.461 (3)
C1—C2	1.396 (3)	C16—C17	1.403 (3)
C1—C6	1.412 (3)	C16—C21	1.405 (3)
C2—C3	1.392 (3)	C17—C18	1.378 (3)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.390 (3)	C18—C19	1.403 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.385 (3)	C19—C20	1.381 (3)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.408 (3)	C20—C21	1.403 (3)
C5—H5	0.9500	C20—H20	0.9500
C7—C8	1.365 (2)	C21—C22	1.480 (3)
C7—C22	1.459 (3)

C7—S1—C1	101.44 (9)	C12—C11—C10	123.48 (17)
C9—O1—C8	117.11 (14)	C12—C11—N3	118.98 (16)
C22—N1—C6	122.71 (17)	C10—C11—N3	117.52 (16)
C15—N2—C14	116.53 (17)	C11—C12—C13	118.21 (18)
O3—N3—O2	123.65 (18)	C11—C12—H12	120.9
O3—N3—C11	118.20 (17)	C13—C12—H12	120.9
O2—N3—C11	118.16 (17)	C12—C13—C14	120.79 (18)
C2—C1—C6	121.09 (18)	C12—C13—H13	119.6
C2—C1—S1	116.71 (16)	C14—C13—H13	119.6
C6—C1—S1	122.20 (15)	N2—C14—C13	119.46 (17)
C3—C2—C1	119.5 (2)	N2—C14—C9	122.28 (17)
C3—C2—H2	120.2	C13—C14—C9	118.26 (17)
C1—C2—H2	120.2	N2—C15—C8	123.61 (17)
C4—C3—C2	120.4 (2)	N2—C15—C16	119.62 (18)
C4—C3—H3	119.8	C8—C15—C16	116.75 (17)
C2—C3—H3	119.8	C17—C16—C21	119.87 (19)
C5—C4—C3	120.12 (19)	C17—C16—C15	119.31 (19)
C5—C4—H4	119.9	C21—C16—C15	120.80 (18)
C3—C4—H4	119.9	C18—C17—C16	120.4 (2)
C4—C5—C6	121.1 (2)	C18—C17—H17	119.8
C4—C5—H5	119.4	C16—C17—H17	119.8
C6—C5—H5	119.4	C17—C18—C19	119.7 (2)
N1—C6—C5	116.49 (18)	C17—C18—H18	120.1
N1—C6—C1	125.70 (17)	C19—C18—H18	120.1
C5—C6—C1	117.77 (19)	C20—C19—C18	120.6 (2)
C8—C7—C22	120.54 (18)	C20—C19—H19	119.7
C8—C7—S1	117.13 (14)	C18—C19—H19	119.7
C22—C7—S1	122.32 (14)	C19—C20—C21	120.3 (2)
C7—C8—O1	116.19 (16)	C19—C20—H20	119.9
C7—C8—C15	124.04 (17)	C21—C20—H20	119.9
O1—C8—C15	119.76 (16)	C20—C21—C16	119.16 (19)
C10—C9—O1	116.98 (16)	C20—C21—C22	120.02 (19)
C10—C9—C14	122.47 (16)	C16—C21—C22	120.79 (17)
O1—C9—C14	120.55 (16)	N1—C22—C7	125.41 (18)
C9—C10—C11	116.70 (16)	N1—C22—C21	117.54 (18)
C9—C10—H10	121.6	C7—C22—C21	117.06 (17)
C11—C10—H10	121.6

C7—S1—C1—C2	175.38 (16)	C12—C13—C14—N2	179.45 (19)
C7—S1—C1—C6	−4.46 (19)	C12—C13—C14—C9	−1.4 (3)
C6—C1—C2—C3	0.7 (3)	C10—C9—C14—N2	−177.73 (18)
S1—C1—C2—C3	−179.14 (16)	O1—C9—C14—N2	2.4 (3)
C1—C2—C3—C4	−0.5 (3)	C10—C9—C14—C13	3.1 (3)
C2—C3—C4—C5	−0.2 (3)	O1—C9—C14—C13	−176.79 (17)
C3—C4—C5—C6	0.7 (3)	C14—N2—C15—C8	−0.4 (3)
C22—N1—C6—C5	−175.21 (19)	C14—N2—C15—C16	−178.93 (16)
C22—N1—C6—C1	2.4 (3)	C7—C8—C15—N2	−176.72 (19)
C4—C5—C6—N1	177.30 (19)	O1—C8—C15—N2	3.7 (3)
C4—C5—C6—C1	−0.5 (3)	C7—C8—C15—C16	1.9 (3)
C2—C1—C6—N1	−177.8 (2)	O1—C8—C15—C16	−177.73 (16)
S1—C1—C6—N1	2.0 (3)	N2—C15—C16—C17	−1.3 (3)
C2—C1—C6—C5	−0.2 (3)	C8—C15—C16—C17	−179.96 (19)
S1—C1—C6—C5	179.61 (15)	N2—C15—C16—C21	176.93 (18)
C1—S1—C7—C8	−177.22 (15)	C8—C15—C16—C21	−1.7 (3)
C1—S1—C7—C22	3.86 (19)	C21—C16—C17—C18	−0.3 (3)
C22—C7—C8—O1	178.25 (16)	C15—C16—C17—C18	177.9 (2)
S1—C7—C8—O1	−0.7 (2)	C16—C17—C18—C19	−0.8 (4)
C22—C7—C8—C15	−1.4 (3)	C17—C18—C19—C20	1.2 (4)
S1—C7—C8—C15	179.71 (16)	C18—C19—C20—C21	−0.3 (4)
C9—O1—C8—C7	176.59 (17)	C19—C20—C21—C16	−0.9 (3)
C9—O1—C8—C15	−3.8 (2)	C19—C20—C21—C22	−179.1 (2)
C8—O1—C9—C10	−178.95 (17)	C17—C16—C21—C20	1.2 (3)
C8—O1—C9—C14	1.0 (2)	C15—C16—C21—C20	−177.03 (19)
O1—C9—C10—C11	178.00 (16)	C17—C16—C21—C22	179.4 (2)
C14—C9—C10—C11	−1.9 (3)	C15—C16—C21—C22	1.1 (3)
C9—C10—C11—C12	−1.1 (3)	C6—N1—C22—C7	−3.1 (3)
C9—C10—C11—N3	−179.50 (16)	C6—N1—C22—C21	176.77 (18)
O3—N3—C11—C12	−6.8 (3)	C8—C7—C22—N1	−179.49 (19)
O2—N3—C11—C12	173.20 (19)	S1—C7—C22—N1	−0.6 (3)
O3—N3—C11—C10	171.68 (18)	C8—C7—C22—C21	0.6 (3)
O2—N3—C11—C10	−8.3 (3)	S1—C7—C22—C21	179.50 (15)
C10—C11—C12—C13	2.7 (3)	C20—C21—C22—N1	−2.3 (3)
N3—C11—C12—C13	−178.88 (18)	C16—C21—C22—N1	179.57 (18)
C11—C12—C13—C14	−1.4 (3)	C20—C21—C22—C7	177.60 (19)
C15—N2—C14—C13	176.55 (18)	C16—C21—C22—C7	−0.5 (3)
C15—N2—C14—C9	−2.6 (3)

Acknowledgements

We are very grateful for the help of Dr Victor Young Jr, director of the X-ray facility at the Department of Chemistry, University of Minnesota, with solving the crystal structure reported. We would like to thank the funding from Wilkes University Department of Chemistry and Biochemistry and the Department of Electrical Engineering and Physics for funding of the project. P-TTP acknowledges support from Penn State Scranton for Professional and Research Development funding.

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