5-([(Z)-Meth­oxy­imino]{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}meth­yl)-1,3,4-oxa­diazole-2(3H)-thione dimethyl sulfoxide monosolvate

Shripanavar, C.S.; Balerao, R.; Butcher, R.J.

doi:10.1107/S2414314623002377

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 3| March 2023| x230237

https://doi.org/10.1107/S2414314623002377

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5-([(Z)-Methoxyimino]{2-[(2-methylphenoxy)methyl]phenyl}methyl)-1,3,4-oxadiazole-2(3H)-thione dimethyl sulfoxide monosolvate

Chetan Shrimandhar Shripanavar,^a ^* Rishik Balerao ^b and Ray J. Butcher ^c

^aChenshri Research Laboratory (OPC) Private Limited, Pattankudi (Karnataka)-, 591238, India, ^bThomas Jefferson High School for Science and Technology, 6560 Braddock Rd, Alexandria VA 22312, USA, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC, 20059, USA
^*Correspondence e-mail: chetan4679@googlemail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 27 February 2023; accepted 11 March 2023; online 28 March 2023)

The title compound, C₁₈H₁₇N₃O₃S·C₂H₆OS, crystallizes in the monoclinic space group P2₁/c. In the crystal, C₁¹(9) chains of C—H⋯O interactions are formed, propogating in the c-axis direction. The N—H hydrogen atom forms a strong hydrogen bond with the oxygen atom of a DMSO solvate molecule.

Keywords: crystal structure; DMSO; fungicides; strobilurin.

CCDC reference: 2247969

Structure description

The newly synthesized title compound C₂H₆OS·C₁₈H₁₇N₃O₃S (1, Fig. 1) is derived from Kresoxim methyl fungicide and is a member of the strobilurin family. The broad spectrum nature of 1 allows it to have site-specific action and high efficacy against fungal diseases (Anke et al.1977 ; Olaya et al. 1998 ; Patel et al., 2012 ; Esteve-Turrillas et al., 2011 ; Mercader et al., 2008 ; Balba, 2007 ; Cash & Cronan, 2001 , Ammermann et al., 2000 ; Balba, 2007; Kant et al., 2012 ). The metabolites of compounds such as 1 are easily translocated in nature. The modified structure of 1 has various antifungal, antibacterial and anticancer properties; however, tracing out the exact mode of action of this type of compound will require further study of its bio-efficacy.

Figure 1
Diagram of 1 showing atom labelling with hydrogen bonding shown as dashed lines and atomic displacement parameters set at the 30% probability level

Compound 1 crystallizes in the monoclinic space group P2₁/c with one strobilurin molecule and one solvent molecule in the asymmetric unit. It consists of a toluene ring linked via a methoxy group to a phenyl ring, which is then linked to a five-membered 1,3,4 oxadiazole-2-thione ring. The carbon atom linking the five-membered ring to the phenyl ring additionally has a methoxyamino substituent branching off from it.

In the crystal of 1, the solvent DMSO molecule accepts both an N—H⋯O hydrogen bond with the five-membered ring and a weak C—H⋯O interaction with an adjacent DMSO molecule (symmetry operation: x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z) (Fig. 2, Table 1). Additionally, the methoxyamino substituent forms a weak C—H⋯O interaction with the methoxy group in an adjacent molecule (symmetry operation: x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z), forming a $[C_{1}^{1}]$ (9) chain propogating in the c-axis direction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.99 (5)	1.65 (5)	2.630 (3)	170 (4)
C4—H4A⋯O3ⁱ	0.98	2.54	3.404 (4)	147
C20—H20C⋯O4ⁱⁱ	0.98	2.45	3.161 (4)	129
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Diagram showing the packing of 1 with hydrogen bonds shown as dashed lines. The molecules of 1 are linked by C—H⋯O interactions forming a $[C_{1}^{1}]$ (9) chain propagating in the c-axis direction.

A pseudopolymorph of this structure has also be determined with water as solvent (Shripanavar et al., 2023 )

Synthesis and crystallization

The Kresoxim methyl hydrazone compound (3.13 g, 0.01 mol) was dissolved in a solution of KOH (0.01 mol) in water (20 ml) and CS₂ (0.01 mol) in ethanol (20 ml) and then the mixture was refluxed for 8 h. After the reaction was complete, the mixture was cooled at room temperature and neutralized with diluted HCl (4 N). The precipitated product was filtered and washed with water to dry it. Crystals were obtained by evaporation of a DMSO solution.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₃S·C₂H₆OS
M_r	433.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	27.0233 (2), 9.00367 (9), 8.96199 (8)
β (°)	94.2689 (8)
V (Å³)	2174.48 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.48
Crystal size (mm)	0.37 × 0.25 × 0.09

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix CCD
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 )
T_min, T_max	0.495, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	79202, 4606, 4232
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.637

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.166, 1.09
No. of reflections	4606
No. of parameters	270
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.42
Computer programs: CrysAlis PRO (Rigaku OD, 2022), SHELXT (Sheldrick, 2015b ), SHELXL2018/3 (Sheldrick, 2015a ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2247969

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002377/bt4133sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002377/bt4133Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623002377/bt4133Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.42.61a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.61a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.61a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015a); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

5-([(Z)-Methoxyimino]{2-[(2-methylphenoxy)methyl]phenyl}methyl)-1,3,4-oxadiazole-2(3H)-thione dimethyl sulfoxide monosolvate top

Crystal data top

C₁₈H₁₇N₃O₃S·C₂H₆OS	F(000) = 912
M_r = 433.53	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 27.0233 (2) Å	Cell parameters from 48963 reflections
b = 9.00367 (9) Å	θ = 3.3–78.7°
c = 8.96199 (8) Å	µ = 2.48 mm⁻¹
β = 94.2689 (8)°	T = 100 K
V = 2174.48 (3) Å³	Plate, colorless
Z = 4	0.37 × 0.25 × 0.09 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix CCD diffractometer	4232 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.070
ω scans	θ_max = 79.0°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	h = −32→34
T_min = 0.495, T_max = 1.000	k = −11→9
79202 measured reflections	l = −11→11
4606 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.074P)² + 4.3637P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
4606 reflections	Δρ_max = 0.92 e Å⁻³
270 parameters	Δρ_min = −0.42 e Å⁻³

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.

Refinement. A riding model was used for the H atoms attached to C with atomic displacement parameters = 1.2U_eq(C) [1.5U_eq(C) for methyl groups] while the N—H hydrogen atom was refined isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S2	0.93981 (2)	0.70551 (7)	0.33974 (7)	0.02729 (19)
S1	0.92357 (3)	0.20933 (8)	0.46944 (8)	0.03022 (19)
O1	0.84852 (7)	0.2364 (2)	0.6449 (2)	0.0247 (4)
O2	0.74155 (7)	0.1493 (2)	0.9232 (2)	0.0278 (4)
O3	0.64096 (7)	0.4321 (2)	0.6557 (2)	0.0296 (4)
O4	0.93495 (8)	0.6691 (2)	0.5039 (2)	0.0323 (5)
N1	0.84213 (8)	0.4796 (2)	0.6822 (3)	0.0258 (5)
N2	0.88048 (8)	0.4488 (3)	0.5933 (3)	0.0267 (5)
H2	0.9011 (17)	0.526 (5)	0.549 (5)	0.069 (14)*
N3	0.77856 (8)	0.1748 (2)	0.8257 (2)	0.0250 (5)
C1	0.88506 (10)	0.3029 (3)	0.5679 (3)	0.0253 (5)
C2	0.82475 (9)	0.3499 (3)	0.7106 (3)	0.0235 (5)
C3	0.78482 (10)	0.3154 (3)	0.8061 (3)	0.0234 (5)
C4	0.73450 (11)	−0.0083 (3)	0.9332 (3)	0.0316 (6)
H4A	0.711008	−0.029760	1.008586	0.047*
H4B	0.766353	−0.056211	0.961975	0.047*
H4C	0.721321	−0.046597	0.835861	0.047*
C5	0.75704 (10)	0.4374 (3)	0.8746 (3)	0.0234 (5)
C6	0.78357 (10)	0.5348 (3)	0.9721 (3)	0.0265 (5)
H6	0.818646	0.526881	0.986990	0.032*
C7	0.75861 (11)	0.6433 (3)	1.0473 (3)	0.0296 (6)
H7	0.776578	0.708605	1.114703	0.036*
C8	0.70765 (11)	0.6562 (3)	1.0241 (3)	0.0304 (6)
H8	0.690546	0.729492	1.076587	0.036*
C9	0.68135 (10)	0.5619 (3)	0.9237 (3)	0.0281 (6)
H9	0.646474	0.573439	0.905669	0.034*
C10	0.70567 (10)	0.4506 (3)	0.8493 (3)	0.0248 (5)
C11	0.67522 (10)	0.3450 (3)	0.7495 (3)	0.0275 (6)
H11A	0.697051	0.286843	0.687417	0.033*
H11B	0.656964	0.275053	0.810603	0.033*
C12	0.60536 (10)	0.3565 (3)	0.5680 (3)	0.0281 (6)
C13	0.59919 (11)	0.2033 (3)	0.5694 (4)	0.0331 (6)
H13	0.620853	0.142935	0.631872	0.040*
C14	0.56100 (12)	0.1388 (4)	0.4785 (4)	0.0398 (7)
H14	0.556604	0.034137	0.479031	0.048*
C15	0.52973 (13)	0.2257 (4)	0.3882 (4)	0.0468 (8)
H15	0.503516	0.181535	0.326974	0.056*
C16	0.53654 (13)	0.3779 (4)	0.3866 (4)	0.0458 (8)
H16	0.514667	0.437152	0.323659	0.055*
C17	0.57434 (11)	0.4464 (4)	0.4742 (4)	0.0353 (6)
C18	0.58288 (13)	0.6118 (4)	0.4704 (5)	0.0477 (9)
H18A	0.555770	0.659212	0.409096	0.072*
H18B	0.614445	0.632245	0.427202	0.072*
H18C	0.583968	0.651520	0.572391	0.072*
C19	0.98058 (11)	0.5696 (4)	0.2734 (3)	0.0349 (6)
H19A	1.014221	0.586410	0.318900	0.052*
H19B	0.980684	0.577262	0.164293	0.052*
H19C	0.969320	0.470396	0.300279	0.052*
C20	0.88338 (11)	0.6408 (4)	0.2451 (4)	0.0385 (7)
H20A	0.855370	0.697025	0.279692	0.058*
H20B	0.879052	0.535046	0.266733	0.058*
H20C	0.884759	0.654678	0.137066	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0319 (4)	0.0229 (3)	0.0273 (3)	−0.0070 (2)	0.0040 (3)	0.0002 (2)
S1	0.0311 (4)	0.0309 (4)	0.0289 (4)	0.0015 (3)	0.0036 (3)	−0.0026 (3)
O1	0.0276 (9)	0.0187 (9)	0.0277 (9)	−0.0018 (7)	0.0025 (7)	−0.0005 (7)
O2	0.0350 (10)	0.0162 (9)	0.0332 (10)	−0.0029 (7)	0.0085 (8)	0.0020 (7)
O3	0.0259 (9)	0.0240 (10)	0.0378 (11)	−0.0017 (7)	−0.0040 (8)	0.0012 (8)
O4	0.0410 (11)	0.0297 (10)	0.0268 (10)	−0.0105 (8)	0.0069 (8)	−0.0031 (8)
N1	0.0278 (11)	0.0208 (11)	0.0287 (11)	−0.0013 (8)	0.0021 (9)	0.0036 (9)
N2	0.0280 (11)	0.0239 (11)	0.0285 (11)	−0.0031 (9)	0.0041 (9)	0.0016 (9)
N3	0.0285 (11)	0.0208 (10)	0.0256 (11)	−0.0022 (8)	0.0029 (9)	0.0009 (9)
C1	0.0274 (13)	0.0249 (13)	0.0231 (12)	−0.0021 (10)	−0.0012 (10)	0.0023 (10)
C2	0.0265 (12)	0.0181 (12)	0.0254 (12)	0.0014 (9)	−0.0006 (10)	0.0002 (9)
C3	0.0257 (12)	0.0186 (12)	0.0253 (12)	−0.0014 (9)	−0.0016 (10)	0.0013 (9)
C4	0.0433 (16)	0.0171 (12)	0.0352 (15)	−0.0072 (11)	0.0087 (12)	−0.0006 (11)
C5	0.0303 (13)	0.0137 (11)	0.0262 (12)	−0.0012 (9)	0.0015 (10)	0.0037 (9)
C6	0.0304 (13)	0.0182 (12)	0.0300 (13)	−0.0013 (10)	−0.0034 (10)	0.0047 (10)
C7	0.0413 (15)	0.0161 (12)	0.0305 (14)	−0.0011 (10)	−0.0039 (11)	0.0015 (10)
C8	0.0401 (15)	0.0153 (12)	0.0360 (15)	0.0011 (11)	0.0048 (12)	0.0029 (10)
C9	0.0299 (13)	0.0187 (12)	0.0359 (14)	0.0002 (10)	0.0035 (11)	0.0028 (10)
C10	0.0295 (13)	0.0165 (12)	0.0284 (13)	−0.0030 (9)	0.0019 (10)	0.0036 (10)
C11	0.0259 (13)	0.0206 (12)	0.0355 (14)	−0.0011 (10)	−0.0008 (11)	0.0019 (11)
C12	0.0237 (12)	0.0306 (14)	0.0300 (13)	−0.0025 (10)	0.0027 (10)	−0.0047 (11)
C13	0.0292 (14)	0.0316 (15)	0.0384 (16)	−0.0012 (11)	0.0025 (12)	−0.0067 (12)
C14	0.0343 (15)	0.0355 (17)	0.0497 (19)	−0.0050 (12)	0.0035 (13)	−0.0137 (14)
C15	0.0359 (17)	0.051 (2)	0.051 (2)	−0.0069 (15)	−0.0074 (14)	−0.0135 (16)
C16	0.0384 (17)	0.049 (2)	0.0479 (19)	−0.0031 (15)	−0.0100 (14)	−0.0001 (16)
C17	0.0302 (14)	0.0368 (16)	0.0382 (16)	−0.0017 (12)	−0.0018 (12)	0.0016 (13)
C18	0.0419 (18)	0.0383 (18)	0.060 (2)	−0.0029 (14)	−0.0146 (15)	0.0120 (16)
C19	0.0339 (15)	0.0394 (17)	0.0316 (14)	−0.0002 (12)	0.0049 (11)	−0.0022 (12)
C20	0.0313 (15)	0.0426 (18)	0.0406 (17)	−0.0074 (13)	−0.0038 (12)	0.0057 (14)

Geometric parameters (Å, º) top

S2—O4	1.523 (2)	C8—C9	1.393 (4)
S2—C19	1.778 (3)	C9—H9	0.9500
S2—C20	1.787 (3)	C9—C10	1.394 (4)
S1—C1	1.645 (3)	C10—C11	1.508 (4)
O1—C1	1.382 (3)	C11—H11A	0.9900
O1—C2	1.364 (3)	C11—H11B	0.9900
O2—N3	1.395 (3)	C12—C13	1.390 (4)
O2—C4	1.436 (3)	C12—C17	1.400 (4)
O3—C11	1.436 (3)	C13—H13	0.9500
O3—C12	1.376 (3)	C13—C14	1.393 (4)
N1—N2	1.382 (3)	C14—H14	0.9500
N1—C2	1.291 (3)	C14—C15	1.371 (5)
N2—H2	0.99 (5)	C15—H15	0.9500
N2—C1	1.340 (4)	C15—C16	1.383 (5)
N3—C3	1.291 (3)	C16—H16	0.9500
C2—C3	1.460 (4)	C16—C17	1.386 (4)
C3—C5	1.488 (4)	C17—C18	1.508 (5)
C4—H4A	0.9800	C18—H18A	0.9800
C4—H4B	0.9800	C18—H18B	0.9800
C4—H4C	0.9800	C18—H18C	0.9800
C5—C6	1.398 (4)	C19—H19A	0.9800
C5—C10	1.395 (4)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800
C6—C7	1.389 (4)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C7—C8	1.382 (4)	C20—H20C	0.9800
C8—H8	0.9500

O4—S2—C19	105.99 (14)	C9—C10—C11	118.8 (2)
O4—S2—C20	104.85 (13)	O3—C11—C10	107.6 (2)
C19—S2—C20	98.34 (16)	O3—C11—H11A	110.2
C2—O1—C1	105.6 (2)	O3—C11—H11B	110.2
N3—O2—C4	107.8 (2)	C10—C11—H11A	110.2
C12—O3—C11	117.2 (2)	C10—C11—H11B	110.2
C2—N1—N2	103.4 (2)	H11A—C11—H11B	108.5
N1—N2—H2	124 (3)	O3—C12—C13	124.4 (3)
C1—N2—N1	112.2 (2)	O3—C12—C17	114.8 (3)
C1—N2—H2	124 (3)	C13—C12—C17	120.8 (3)
C3—N3—O2	110.7 (2)	C12—C13—H13	120.3
O1—C1—S1	123.4 (2)	C12—C13—C14	119.5 (3)
N2—C1—S1	131.5 (2)	C14—C13—H13	120.3
N2—C1—O1	105.1 (2)	C13—C14—H14	119.8
O1—C2—C3	119.1 (2)	C15—C14—C13	120.3 (3)
N1—C2—O1	113.7 (2)	C15—C14—H14	119.8
N1—C2—C3	127.1 (2)	C14—C15—H15	120.2
N3—C3—C2	113.5 (2)	C14—C15—C16	119.7 (3)
N3—C3—C5	126.3 (2)	C16—C15—H15	120.2
C2—C3—C5	120.1 (2)	C15—C16—H16	119.0
O2—C4—H4A	109.5	C15—C16—C17	121.9 (3)
O2—C4—H4B	109.5	C17—C16—H16	119.0
O2—C4—H4C	109.5	C12—C17—C18	119.9 (3)
H4A—C4—H4B	109.5	C16—C17—C12	117.7 (3)
H4A—C4—H4C	109.5	C16—C17—C18	122.3 (3)
H4B—C4—H4C	109.5	C17—C18—H18A	109.5
C6—C5—C3	118.0 (2)	C17—C18—H18B	109.5
C10—C5—C3	121.5 (2)	C17—C18—H18C	109.5
C10—C5—C6	120.4 (2)	H18A—C18—H18B	109.5
C5—C6—H6	120.0	H18A—C18—H18C	109.5
C7—C6—C5	120.0 (3)	H18B—C18—H18C	109.5
C7—C6—H6	120.0	S2—C19—H19A	109.5
C6—C7—H7	120.0	S2—C19—H19B	109.5
C8—C7—C6	120.0 (3)	S2—C19—H19C	109.5
C8—C7—H7	120.0	H19A—C19—H19B	109.5
C7—C8—H8	120.0	H19A—C19—H19C	109.5
C7—C8—C9	120.0 (3)	H19B—C19—H19C	109.5
C9—C8—H8	120.0	S2—C20—H20A	109.5
C8—C9—H9	119.6	S2—C20—H20B	109.5
C8—C9—C10	120.7 (3)	S2—C20—H20C	109.5
C10—C9—H9	119.6	H20A—C20—H20B	109.5
C5—C10—C11	122.4 (2)	H20A—C20—H20C	109.5
C9—C10—C5	118.8 (2)	H20B—C20—H20C	109.5

O1—C2—C3—N3	4.4 (3)	C3—C5—C10—C11	−1.2 (4)
O1—C2—C3—C5	−177.7 (2)	C4—O2—N3—C3	176.7 (2)
O2—N3—C3—C2	177.3 (2)	C5—C6—C7—C8	−0.9 (4)
O2—N3—C3—C5	−0.5 (4)	C5—C10—C11—O3	−135.1 (2)
O3—C12—C13—C14	178.3 (3)	C6—C5—C10—C9	−0.4 (4)
O3—C12—C17—C16	−177.8 (3)	C6—C5—C10—C11	−177.8 (2)
O3—C12—C17—C18	2.5 (4)	C6—C7—C8—C9	−0.9 (4)
N1—N2—C1—S1	179.2 (2)	C7—C8—C9—C10	2.1 (4)
N1—N2—C1—O1	−0.7 (3)	C8—C9—C10—C5	−1.4 (4)
N1—C2—C3—N3	−173.5 (3)	C8—C9—C10—C11	176.1 (2)
N1—C2—C3—C5	4.4 (4)	C9—C10—C11—O3	47.5 (3)
N2—N1—C2—O1	−0.9 (3)	C10—C5—C6—C7	1.6 (4)
N2—N1—C2—C3	177.1 (2)	C11—O3—C12—C13	2.9 (4)
N3—C3—C5—C6	116.6 (3)	C11—O3—C12—C17	−177.4 (2)
N3—C3—C5—C10	−60.1 (4)	C12—O3—C11—C10	−172.3 (2)
C1—O1—C2—N1	0.5 (3)	C12—C13—C14—C15	0.0 (5)
C1—O1—C2—C3	−177.6 (2)	C13—C12—C17—C16	1.9 (5)
C2—O1—C1—S1	−179.72 (19)	C13—C12—C17—C18	−177.8 (3)
C2—O1—C1—N2	0.1 (3)	C13—C14—C15—C16	0.6 (5)
C2—N1—N2—C1	1.0 (3)	C14—C15—C16—C17	0.0 (6)
C2—C3—C5—C6	−61.1 (3)	C15—C16—C17—C12	−1.3 (5)
C2—C3—C5—C10	122.3 (3)	C15—C16—C17—C18	178.4 (4)
C3—C5—C6—C7	−175.1 (2)	C17—C12—C13—C14	−1.3 (4)
C3—C5—C10—C9	176.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.99 (5)	1.65 (5)	2.630 (3)	170 (4)
C4—H4A···O3ⁱ	0.98	2.54	3.404 (4)	147
C11—H11A···N3	0.99	2.65	3.214 (3)	117
C20—H20C···O4ⁱⁱ	0.98	2.45	3.161 (4)	129

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2.

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