tert-Butyl 5-{2-[2-(N-ethynyl-4-methyl­benzene­sulfonamido)­phen­yl]ethyn­yl}furan-2-carboxyl­ate

Dassonneville, B.; Detert, H.; Schollmeyer, D.

doi:10.1107/S2414314625006558

organic compounds

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ISSN: 2414-3146

Volume 10| Part 8| August 2025| x250655

https://doi.org/10.1107/S2414314625006558

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tert-Butyl 5-{2-[2-(N-ethynyl-4-methylbenzenesulfonamido)phenyl]ethynyl}furan-2-carboxylate

Benjamin Dassonneville,^a Heiner Detert ^a ^* and Dieter Schollmeyer ^a

^aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 25 June 2025; accepted 21 July 2025; online 15 August 2025)

The crystal structure of an o,N-dialkynyltosylaniline, C₂₆H₂₃NO₅S, is presented. Two essentially planar and nearly parallel branches are connected to the aniline unit and the angle between the alkynes amounts to 26 (4)°. Weak intramolecular aromatic π–π stacking occurs.

Keywords: crystal structure; ynamide; diyne; furane.

CCDC reference: 2474369

Structure description

In a project on heterocarbazoles (Letessier et al., 2012 , 2013 ; Letessier & Detert, 2012 ), the title compound, C₂₆H₂₃NO₅S (I), was prepared as substrate for a study on rhodium-catalyzed 2 + 2 + 2 cycloadditions of alkynylynamides to carbolines (Nissen & Detert, 2011 ) and indolothiopyranes (Dassonneville et al., 2023a ,b ). This compound is a key intermediate in the synthesis of isoperlolyrine (Dassonneville et al., 2011 ).

The crystal structure of (I) shows (Fig. 1) that two near planar segments are connected to the N-ethynylaniline unit. The furan ring (C9–C12/O13) and the tolyl ring (C27–C32) include an angle of 9.01 (5)°; the distance between the centroids of these rings is 4.0830 (5) Å with a slippage of 2.105 Å. The alkynylfurancarboxylic ester unit (C7–C12/O13/C14/O15) is essentially planar with a maximum deviation of 0.1111 (8) Å at C1. The dihedral angle between the furan (C9–C12/O13) and aniline ring (C1–C6) is 33.53 (5) ° and the alkyne units N21/C22/C23 and C1/C7/C8/C9 subtend an angle of 26 (4)°. In the crystal, two molecules fill the triclinic unit cell and neighboring molecules are connected via van der Waals interactions and a center of inversion (Fig. 2).

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

Figure 2
Part of the packing diagram viewed along the b-axis direction. Hydrogen atoms omitted for clarity.

Synthesis and crystallization

Synthetic details are given in the literature (Dassonneville et al., 2011). Assignment of signals is based on two-dimensional NMR, notation follows IUPAC nomenclature. The compound was obtained as white solid, m.p.= 384–385 K. ¹H NMR (400 MHz, CDCl₃, 298 K):7.69 (d, ³J_H,H = 8.2 Hz, 2H, 2-H, 6-H Ts), 7.49 (d, ³J_H,H = 7.0 Hz, 1H, 3-H), 7.43 (m, 3H, 4-H, 5-H, 6-H), 7.21 (d, ³J_H,H = 8.2 Hz, 2H, 3-H, 5-H Ts), 7.04 (d, ³J_H,H = 3.5 Hz, 1H, 4-H Fu), 6.53 (d, ³J_H,H = 3.5 Hz, 1H, 3-H Fu), 2.90 (s, 1H, 8-H), 2.31 (s, 3H, CH₃ Ts), 1.60 (s, 9H, ^tBu). ¹³C NMR (CDCl3): 157.2 (C_q, COOtBu), 145.9 (C_q, C-5 Fu), 145.1 (C_q, C-4 T s), 139.2 (C_q, C-1), 138.3 (C_q, C-2 Fu), 133.9 (C_q, C-1 T s), 133.3 (CH, C-3), 130.1 (CH, C-4), 130.0 (CH, C-6), 129.7 (CH, C-3, C-5 T s), 129.2 (CH, C-5), 128.3 (CH, C-2, C-6 T s), 121.2 (C_q, C-2), 117.7 (CH, C-4 Fu), 117.2 (CH, C-3 Fu), 90.0 (C_q Ph—CC—Fu), 84.4 (C_q, Ph—CC—Fu), 82.3 (C_q, C(CH₃)3), 75.4 (C_q, N—CC—H), 59.3 (CH, N—CC—H), 28.2 (CH₃, tBu), 21.5 (CH₃ Ts). IR (neat): 3289, 2988, 2129, 1722, 1516, 1375, 1307, 1173, 1137, 1010, 766 cm⁻¹. FD–MS: m/z (%) = 461.0 (100) [M]^+. C₂₆H₂₃NO₅S (461.13) calculated C 67.66, H 5.02, N 3.03, S 6.95; found C 67.43, H 4.93, N 3.01, S 6.67.

Refinement

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

Table 1
Experimental details

Crystal data
Chemical formula	C₂₆H₂₃NO₅S
M_r	461.51
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	120
a, b, c (Å)	7.7527 (3), 12.6007 (5), 13.7529 (5)
α, β, γ (°)	66.199 (3), 76.607 (3), 80.350 (3)
V (Å³)	1191.66 (8)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.51 × 0.45 × 0.37

Data collection
Diffractometer	Stoe Stadivsri
Absorption correction	Integration
T_min, T_max	0.899, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	21571, 8903, 7763
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.804

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.114, 1.06
No. of reflections	8903
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.50
Computer programs: X-AREA WinXpose, Recipe and Integrate (Stoe & Cie, 2020 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 2474369

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314625006558/hb4528sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625006558/hb4528Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625006558/hb4528Isup3.cml

checkCIF report

Computing details top

tert-Butyl 5-{2-[2-(N-ethynyl-4-methylbenzenesulfonamido)phenyl]ethynyl}furan-2-carboxylate top

Crystal data top

C₂₆H₂₃NO₅S	F(000) = 484
M_r = 461.51	D_x = 1.286 Mg m⁻³
Triclinic, P1	Melting point: 384 K
a = 7.7527 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.6007 (5) Å	Cell parameters from 33755 reflections
c = 13.7529 (5) Å	θ = 2.7–34.8°
α = 66.199 (3)°	µ = 0.17 mm⁻¹
β = 76.607 (3)°	T = 120 K
γ = 80.350 (3)°	Block, colorless
V = 1191.66 (8) Å³	0.51 × 0.45 × 0.37 mm
Z = 2

Data collection top

Stoe Stadivsri diffractometer	8903 independent reflections
Radiation source: Axo Mo	7763 reflections with I > 2σ(I)
Detector resolution: 13.33 pixels mm^-1	R_int = 0.018
rotation method, ω scans	θ_max = 34.8°, θ_min = 2.7°
Absorption correction: integration	h = −12→12
T_min = 0.899, T_max = 0.955	k = −18→18
21571 measured reflections	l = −19→21

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0733P)² + 0.1217P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
8903 reflections	Δρ_max = 0.43 e Å⁻³
302 parameters	Δρ_min = −0.50 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.

Refinement. Hydrogen atoms attached to carbon atoms were placed at calculated positions and were refined in the riding-model approximation with C—H = 0.99 Å, and with U_iso(H) = 1.2 U_eq(C).

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

	x	y	z	U_iso*/U_eq
C1	0.65107 (10)	0.32278 (7)	−0.19892 (6)	0.01866 (13)
C2	0.55638 (11)	0.26355 (7)	−0.23392 (7)	0.02295 (14)
H2	0.492155	0.200048	−0.182434	0.028*
C3	0.55562 (12)	0.29685 (8)	−0.34311 (7)	0.02667 (16)
H3	0.490861	0.256310	−0.366082	0.032*
C4	0.64960 (12)	0.38951 (8)	−0.41885 (7)	0.02534 (15)
H4	0.650538	0.411245	−0.493626	0.030*
C5	0.74236 (11)	0.45066 (7)	−0.38581 (6)	0.02202 (14)
H5	0.805253	0.514593	−0.437702	0.026*
C6	0.74237 (10)	0.41758 (6)	−0.27644 (6)	0.01835 (13)
C7	0.65771 (10)	0.28461 (7)	−0.08693 (6)	0.02025 (14)
C8	0.67369 (11)	0.25010 (7)	0.00618 (6)	0.02139 (14)
C9	0.70200 (11)	0.21554 (7)	0.11283 (6)	0.02034 (13)
C10	0.73297 (12)	0.27686 (7)	0.16843 (6)	0.02385 (15)
H10	0.735045	0.358862	0.143447	0.029*
C11	0.76142 (11)	0.19355 (7)	0.27098 (6)	0.02309 (15)
H11	0.787304	0.208616	0.328216	0.028*
C12	0.74427 (11)	0.08751 (7)	0.27112 (6)	0.02079 (14)
O13	0.70783 (8)	0.09883 (5)	0.17451 (4)	0.02131 (11)
C14	0.75674 (12)	−0.03284 (7)	0.35009 (6)	0.02299 (15)
O15	0.74907 (12)	−0.11598 (6)	0.32893 (5)	0.03557 (17)
O16	0.77637 (9)	−0.03494 (5)	0.44483 (5)	0.02390 (12)
C17	0.79837 (13)	−0.14879 (7)	0.53537 (6)	0.02594 (16)
C18	0.64352 (15)	−0.22090 (9)	0.56027 (7)	0.03345 (19)
H18A	0.532091	−0.170721	0.557720	0.050*
H18B	0.639044	−0.282360	0.632535	0.050*
H18C	0.659550	−0.256150	0.506632	0.050*
C19	0.97710 (15)	−0.21039 (10)	0.50736 (9)	0.0397 (2)
H19A	0.976867	−0.230521	0.445612	0.060*
H19B	0.998354	−0.281528	0.569635	0.060*
H19C	1.071458	−0.158875	0.488766	0.060*
C20	0.79498 (18)	−0.11173 (10)	0.62842 (8)	0.0389 (2)
H20A	0.893700	−0.063671	0.610406	0.058*
H20B	0.807097	−0.180978	0.694009	0.058*
H20C	0.681962	−0.066703	0.640712	0.058*
N21	0.83817 (9)	0.48321 (6)	−0.24387 (5)	0.02043 (12)
C22	0.75138 (12)	0.52801 (7)	−0.16914 (7)	0.02340 (15)
C23	0.67232 (13)	0.56911 (8)	−0.10549 (8)	0.02971 (17)
H23	0.609321	0.601863	−0.054762	0.036*
S24	1.06219 (3)	0.45912 (2)	−0.25700 (2)	0.02193 (6)
O25	1.11953 (9)	0.43671 (7)	−0.35390 (5)	0.02992 (14)
O26	1.11886 (10)	0.55567 (6)	−0.24649 (6)	0.03253 (15)
C27	1.10259 (10)	0.33213 (7)	−0.14669 (6)	0.01959 (13)
C28	1.12413 (12)	0.33950 (7)	−0.05187 (7)	0.02338 (15)
H28	1.115412	0.412941	−0.046160	0.028*
C29	1.15851 (12)	0.23764 (8)	0.03392 (7)	0.02635 (16)
H29	1.174212	0.241690	0.098796	0.032*
C30	1.17050 (11)	0.12906 (7)	0.02674 (7)	0.02526 (15)
C31	1.14652 (12)	0.12424 (7)	−0.06865 (7)	0.02553 (16)
H31	1.153974	0.050772	−0.074146	0.031*
C32	1.11193 (11)	0.22493 (7)	−0.15577 (7)	0.02261 (14)
H32	1.094929	0.220920	−0.220394	0.027*
C33	1.21211 (17)	0.01939 (9)	0.12007 (9)	0.0400 (2)
H33A	1.214581	−0.048230	0.101444	0.060*
H33B	1.120403	0.013194	0.184114	0.060*
H33C	1.328395	0.021903	0.135330	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0189 (3)	0.0192 (3)	0.0153 (3)	−0.0005 (2)	−0.0048 (2)	−0.0035 (2)
C2	0.0215 (3)	0.0238 (3)	0.0229 (3)	−0.0040 (3)	−0.0069 (3)	−0.0058 (3)
C3	0.0273 (4)	0.0314 (4)	0.0254 (4)	−0.0037 (3)	−0.0107 (3)	−0.0112 (3)
C4	0.0289 (4)	0.0305 (4)	0.0181 (3)	−0.0009 (3)	−0.0091 (3)	−0.0087 (3)
C5	0.0266 (3)	0.0227 (3)	0.0144 (3)	−0.0018 (3)	−0.0060 (3)	−0.0036 (3)
C6	0.0209 (3)	0.0183 (3)	0.0150 (3)	−0.0006 (2)	−0.0057 (2)	−0.0046 (2)
C7	0.0207 (3)	0.0197 (3)	0.0173 (3)	−0.0014 (2)	−0.0038 (2)	−0.0038 (3)
C8	0.0230 (3)	0.0207 (3)	0.0172 (3)	−0.0013 (3)	−0.0039 (2)	−0.0039 (3)
C9	0.0242 (3)	0.0189 (3)	0.0154 (3)	−0.0010 (2)	−0.0046 (2)	−0.0037 (2)
C10	0.0316 (4)	0.0187 (3)	0.0205 (3)	−0.0027 (3)	−0.0079 (3)	−0.0048 (3)
C11	0.0295 (4)	0.0222 (3)	0.0186 (3)	−0.0017 (3)	−0.0079 (3)	−0.0070 (3)
C12	0.0277 (4)	0.0197 (3)	0.0138 (3)	0.0003 (3)	−0.0060 (2)	−0.0050 (2)
O13	0.0311 (3)	0.0183 (2)	0.0133 (2)	−0.0011 (2)	−0.0060 (2)	−0.00406 (19)
C14	0.0324 (4)	0.0202 (3)	0.0144 (3)	0.0005 (3)	−0.0053 (3)	−0.0049 (3)
O15	0.0664 (5)	0.0211 (3)	0.0198 (3)	−0.0015 (3)	−0.0098 (3)	−0.0080 (2)
O16	0.0361 (3)	0.0198 (3)	0.0150 (2)	−0.0003 (2)	−0.0090 (2)	−0.0043 (2)
C17	0.0354 (4)	0.0220 (4)	0.0158 (3)	−0.0018 (3)	−0.0086 (3)	−0.0006 (3)
C18	0.0424 (5)	0.0314 (4)	0.0222 (4)	−0.0104 (4)	−0.0058 (3)	−0.0028 (3)
C19	0.0388 (5)	0.0319 (5)	0.0348 (5)	0.0071 (4)	−0.0106 (4)	−0.0005 (4)
C20	0.0603 (7)	0.0381 (5)	0.0194 (4)	−0.0089 (5)	−0.0157 (4)	−0.0055 (4)
N21	0.0248 (3)	0.0193 (3)	0.0175 (3)	−0.0024 (2)	−0.0063 (2)	−0.0058 (2)
C22	0.0302 (4)	0.0184 (3)	0.0218 (3)	−0.0002 (3)	−0.0102 (3)	−0.0057 (3)
C23	0.0339 (4)	0.0285 (4)	0.0319 (4)	0.0017 (3)	−0.0097 (3)	−0.0164 (4)
S24	0.02414 (10)	0.02249 (10)	0.01708 (9)	−0.00750 (7)	−0.00447 (6)	−0.00286 (7)
O25	0.0271 (3)	0.0417 (4)	0.0170 (3)	−0.0068 (3)	−0.0005 (2)	−0.0075 (2)
O26	0.0395 (4)	0.0240 (3)	0.0332 (3)	−0.0138 (3)	−0.0139 (3)	−0.0016 (3)
C27	0.0197 (3)	0.0208 (3)	0.0180 (3)	−0.0032 (2)	−0.0035 (2)	−0.0064 (3)
C28	0.0304 (4)	0.0210 (3)	0.0210 (3)	−0.0020 (3)	−0.0091 (3)	−0.0079 (3)
C29	0.0337 (4)	0.0246 (4)	0.0213 (3)	−0.0021 (3)	−0.0108 (3)	−0.0063 (3)
C30	0.0245 (4)	0.0215 (3)	0.0262 (4)	−0.0010 (3)	−0.0065 (3)	−0.0048 (3)
C31	0.0259 (4)	0.0209 (3)	0.0303 (4)	−0.0010 (3)	−0.0038 (3)	−0.0113 (3)
C32	0.0229 (3)	0.0246 (4)	0.0224 (3)	−0.0028 (3)	−0.0028 (3)	−0.0115 (3)
C33	0.0497 (6)	0.0256 (4)	0.0370 (5)	0.0020 (4)	−0.0172 (4)	−0.0011 (4)

Geometric parameters (Å, º) top

C1—C2	1.4018 (11)	C18—H18B	0.9800
C1—C6	1.4037 (10)	C18—H18C	0.9800
C1—C7	1.4272 (10)	C19—H19A	0.9800
C2—C3	1.3878 (11)	C19—H19B	0.9800
C2—H2	0.9500	C19—H19C	0.9800
C3—C4	1.3896 (13)	C20—H20A	0.9800
C3—H3	0.9500	C20—H20B	0.9800
C4—C5	1.3918 (11)	C20—H20C	0.9800
C4—H4	0.9500	N21—C22	1.3594 (11)
C5—C6	1.3894 (10)	N21—S24	1.6921 (7)
C5—H5	0.9500	C22—C23	1.1922 (12)
C6—N21	1.4475 (10)	C23—H23	0.9500
C7—C8	1.2043 (11)	S24—O25	1.4283 (7)
C8—C9	1.4109 (10)	S24—O26	1.4299 (7)
C9—C10	1.3651 (11)	S24—C27	1.7472 (8)
C9—O13	1.3685 (9)	C27—C28	1.3931 (10)
C10—C11	1.4182 (11)	C27—C32	1.3946 (11)
C10—H10	0.9500	C28—C29	1.3854 (11)
C11—C12	1.3639 (11)	C28—H28	0.9500
C11—H11	0.9500	C29—C30	1.3974 (12)
C12—O13	1.3685 (9)	C29—H29	0.9500
C12—C14	1.4693 (11)	C30—C31	1.3930 (12)
C14—O15	1.2086 (10)	C30—C33	1.5073 (13)
C14—O16	1.3357 (9)	C31—C32	1.3875 (12)
O16—C17	1.4873 (10)	C31—H31	0.9500
C17—C19	1.5180 (14)	C32—H32	0.9500
C17—C18	1.5193 (14)	C33—H33A	0.9800
C17—C20	1.5228 (13)	C33—H33B	0.9800
C18—H18A	0.9800	C33—H33C	0.9800

C2—C1—C6	118.61 (7)	H18B—C18—H18C	109.5
C2—C1—C7	120.18 (7)	C17—C19—H19A	109.5
C6—C1—C7	121.19 (7)	C17—C19—H19B	109.5
C3—C2—C1	120.59 (8)	H19A—C19—H19B	109.5
C3—C2—H2	119.7	C17—C19—H19C	109.5
C1—C2—H2	119.7	H19A—C19—H19C	109.5
C2—C3—C4	119.99 (8)	H19B—C19—H19C	109.5
C2—C3—H3	120.0	C17—C20—H20A	109.5
C4—C3—H3	120.0	C17—C20—H20B	109.5
C3—C4—C5	120.40 (7)	H20A—C20—H20B	109.5
C3—C4—H4	119.8	C17—C20—H20C	109.5
C5—C4—H4	119.8	H20A—C20—H20C	109.5
C6—C5—C4	119.56 (7)	H20B—C20—H20C	109.5
C6—C5—H5	120.2	C22—N21—C6	119.08 (7)
C4—C5—H5	120.2	C22—N21—S24	117.23 (6)
C5—C6—C1	120.84 (7)	C6—N21—S24	119.20 (5)
C5—C6—N21	118.60 (7)	C23—C22—N21	178.24 (9)
C1—C6—N21	120.56 (6)	C22—C23—H23	180.0
C8—C7—C1	176.13 (8)	O25—S24—O26	121.34 (4)
C7—C8—C9	175.78 (9)	O25—S24—N21	104.93 (4)
C10—C9—O13	110.83 (7)	O26—S24—N21	105.16 (4)
C10—C9—C8	132.13 (7)	O25—S24—C27	109.12 (4)
O13—C9—C8	116.98 (7)	O26—S24—C27	109.34 (4)
C9—C10—C11	106.20 (7)	N21—S24—C27	105.74 (4)
C9—C10—H10	126.9	C28—C27—C32	121.37 (7)
C11—C10—H10	126.9	C28—C27—S24	119.82 (6)
C12—C11—C10	106.38 (7)	C32—C27—S24	118.81 (6)
C12—C11—H11	126.8	C29—C28—C27	118.72 (7)
C10—C11—H11	126.8	C29—C28—H28	120.6
C11—C12—O13	110.77 (7)	C27—C28—H28	120.6
C11—C12—C14	134.61 (7)	C28—C29—C30	121.17 (8)
O13—C12—C14	114.62 (7)	C28—C29—H29	119.4
C9—O13—C12	105.83 (6)	C30—C29—H29	119.4
O15—C14—O16	126.62 (7)	C31—C30—C29	118.88 (8)
O15—C14—C12	122.82 (7)	C31—C30—C33	120.74 (8)
O16—C14—C12	110.56 (7)	C29—C30—C33	120.37 (8)
C14—O16—C17	119.45 (6)	C32—C31—C30	121.11 (8)
O16—C17—C19	108.92 (7)	C32—C31—H31	119.4
O16—C17—C18	110.75 (7)	C30—C31—H31	119.4
C19—C17—C18	112.81 (9)	C31—C32—C27	118.75 (7)
O16—C17—C20	102.12 (7)	C31—C32—H32	120.6
C19—C17—C20	111.31 (9)	C27—C32—H32	120.6
C18—C17—C20	110.42 (8)	C30—C33—H33A	109.5
C17—C18—H18A	109.5	C30—C33—H33B	109.5
C17—C18—H18B	109.5	H33A—C33—H33B	109.5
H18A—C18—H18B	109.5	C30—C33—H33C	109.5
C17—C18—H18C	109.5	H33A—C33—H33C	109.5
H18A—C18—H18C	109.5	H33B—C33—H33C	109.5

C6—C1—C2—C3	1.09 (12)	C14—O16—C17—C20	−173.94 (8)
C7—C1—C2—C3	−177.15 (8)	C5—C6—N21—C22	126.08 (8)
C1—C2—C3—C4	0.14 (13)	C1—C6—N21—C22	−53.72 (10)
C2—C3—C4—C5	−1.10 (14)	C5—C6—N21—S24	−78.34 (8)
C3—C4—C5—C6	0.80 (13)	C1—C6—N21—S24	101.86 (8)
C4—C5—C6—C1	0.45 (12)	C22—N21—S24—O25	−168.07 (6)
C4—C5—C6—N21	−179.35 (7)	C6—N21—S24—O25	35.91 (7)
C2—C1—C6—C5	−1.38 (11)	C22—N21—S24—O26	−39.02 (7)
C7—C1—C6—C5	176.84 (7)	C6—N21—S24—O26	164.96 (6)
C2—C1—C6—N21	178.42 (7)	C22—N21—S24—C27	76.63 (7)
C7—C1—C6—N21	−3.37 (11)	C6—N21—S24—C27	−79.40 (6)
O13—C9—C10—C11	0.49 (10)	O25—S24—C27—C28	155.33 (7)
C8—C9—C10—C11	−176.59 (9)	O26—S24—C27—C28	20.49 (8)
C9—C10—C11—C12	−0.53 (10)	N21—S24—C27—C28	−92.27 (7)
C10—C11—C12—O13	0.40 (10)	O25—S24—C27—C32	−24.89 (7)
C10—C11—C12—C14	−179.88 (9)	O26—S24—C27—C32	−159.73 (7)
C10—C9—O13—C12	−0.25 (9)	N21—S24—C27—C32	87.51 (7)
C8—C9—O13—C12	177.32 (7)	C32—C27—C28—C29	1.12 (13)
C11—C12—O13—C9	−0.11 (9)	S24—C27—C28—C29	−179.11 (7)
C14—C12—O13—C9	−179.89 (7)	C27—C28—C29—C30	−0.42 (14)
C11—C12—C14—O15	−174.32 (10)	C28—C29—C30—C31	−0.25 (14)
O13—C12—C14—O15	5.40 (13)	C28—C29—C30—C33	178.61 (9)
C11—C12—C14—O16	5.91 (14)	C29—C30—C31—C32	0.25 (13)
O13—C12—C14—O16	−174.38 (7)	C33—C30—C31—C32	−178.62 (9)
O15—C14—O16—C17	2.46 (14)	C30—C31—C32—C27	0.43 (13)
C12—C14—O16—C17	−177.77 (7)	C28—C27—C32—C31	−1.13 (12)
C14—O16—C17—C19	68.25 (10)	S24—C27—C32—C31	179.10 (6)
C14—O16—C17—C18	−56.37 (10)

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