21-(4-Methyl-phenyl-sulfon-yl)-4,7,13,16-tetra-oxa-1,10,21-triaza-bicyclo-[8.8.5]tricosane-19,23-dione: an N-tosyl-ated macrobicyclic dilactam.

The macrobicyclic title compound, C(23)H(35)N(3)O(8)S, contains two tertiary amide bridgehead N atoms and a toluene-sulfonamide N atom in the center of the five-atom bridging strand. The mol-ecule has a central cavity that is defined by the 18-membered ring identified by the N(2)O(4) donor atom set and two 15-membered rings with N(3)O(2) donor atom sets. The toluene-sulfonamide N atom adopts an exo orientation with respect to the central cavity, and the tosyl group is oriented on one side of the aza-bridging strand that connects the bridgehead N atoms.

Related literature

For general background to bicyclic dilactams as cation receptors, see: Hourdakis & Popov (1977 ▶); Tümmler et al. (1977 ▶); Buschmann, (1986 ▶); Pietraszkiewicz et al. (1992 ▶); Wanichacheva et al. (2006a ▶,b ▶). For related structures, see: Fields et al. (1986 ▶); Tarnowska et al. (2004 ▶). For the synthesis, see: Lehn & Montavon (1976 ▶, 1978 ▶); Lehn et al. (1977 ▶); Frère & Gramain (1982 ▶); Pietraszkiewicz et al. (1992 ▶); Wanichacheva et al. (2006a ▶,b ▶).

Experimental

Crystal data

C23H35N3O8S

M = 513.60

Monoclinic,

a = 12.807 (2) Å

b = 20.096 (3) Å

c = 10.3305 (17) Å

β = 112.949 (3)°

V = 2448.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.45 × 0.34 × 0.02 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.921, T max = 0.996

22174 measured reflections

5330 independent reflections

3651 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.152

S = 1.00

5330 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.74 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018873/pk2323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018873/pk2323Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018873/pk2323Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H35N3O8S	F(000) = 1096
Mr = 513.60	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7056 reflections
a = 12.807 (2) Å	θ = 2.4–26.8°
b = 20.096 (3) Å	µ = 0.19 mm−1
c = 10.3305 (17) Å	T = 100 K
β = 112.949 (3)°	Plate, colorless
V = 2448.3 (7) Å3	0.45 × 0.34 × 0.02 mm
Z = 4

Bruker APEX CCD diffractometer	5330 independent reflections
Radiation source: fine-focus sealed tube	3651 reflections with I > 2σ(I)
graphite	Rint = 0.078
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→16
Tmin = 0.921, Tmax = 0.996	k = −25→25
22174 measured reflections	l = −13→13

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.090P)2 + ] where P = (Fo2 + 2Fc2)/3
5330 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.87 e Å−3
0 restraints	Δρmin = −0.74 e Å−3

	x	y	z	Uiso*/Ueq
S1	1.09333 (5)	0.25045 (3)	0.83451 (6)	0.01752 (16)
O31	1.09605 (15)	0.22025 (8)	0.71044 (17)	0.0212 (4)
O32	1.08925 (14)	0.20910 (8)	0.94505 (17)	0.0213 (4)
O33	0.79170 (15)	0.24397 (8)	0.79188 (18)	0.0237 (4)
O34	1.03764 (15)	0.42449 (8)	0.72294 (18)	0.0233 (4)
N1	0.77810 (17)	0.31622 (9)	0.9521 (2)	0.0190 (4)
C2	0.6686 (2)	0.28984 (12)	0.9424 (3)	0.0235 (6)
H2A	0.6390	0.3198	0.9962	0.028*
H2B	0.6823	0.2460	0.9897	0.028*
C3	0.5777 (2)	0.28131 (12)	0.7980 (3)	0.0232 (6)
H3A	0.5988	0.2448	0.7484	0.028*
H3B	0.5054	0.2691	0.8057	0.028*
O4	0.56315 (14)	0.34114 (8)	0.72001 (18)	0.0247 (4)
C5	0.4764 (2)	0.33533 (14)	0.5853 (3)	0.0296 (6)
H5A	0.4018	0.3350	0.5931	0.036*
H5B	0.4850	0.2928	0.5419	0.036*
C6	0.4817 (2)	0.39256 (15)	0.4942 (3)	0.0322 (7)
H6A	0.4072	0.3971	0.4149	0.039*
H6B	0.4961	0.4341	0.5499	0.039*
O7	0.56706 (15)	0.38508 (10)	0.43936 (19)	0.0326 (5)
C8	0.6766 (2)	0.40118 (12)	0.5372 (3)	0.0240 (6)
H8A	0.7052	0.3655	0.6084	0.029*
H8B	0.6745	0.4433	0.5859	0.029*
C9	0.7540 (2)	0.40869 (12)	0.4576 (3)	0.0215 (5)
H9A	0.7651	0.3647	0.4217	0.026*
H9B	0.7177	0.4384	0.3759	0.026*
N10	0.86434 (17)	0.43611 (9)	0.5476 (2)	0.0200 (4)
C11	0.8809 (2)	0.50799 (11)	0.5374 (3)	0.0230 (6)
H11A	0.8792	0.5180	0.4428	0.028*
H11B	0.9570	0.5203	0.6070	0.028*
C12	0.7929 (2)	0.55061 (12)	0.5623 (3)	0.0244 (6)
H12A	0.8161	0.5978	0.5666	0.029*
H12B	0.7198	0.5457	0.4808	0.029*
O13	0.77576 (15)	0.53522 (8)	0.68612 (17)	0.0226 (4)
C14	0.8673 (2)	0.55091 (12)	0.8130 (3)	0.0239 (6)
H14A	0.8822	0.5994	0.8183	0.029*
H14B	0.9367	0.5275	0.8177	0.029*
C15	0.8367 (2)	0.52969 (11)	0.9315 (3)	0.0236 (6)
H15A	0.8870	0.5517	1.0194	0.028*
H15B	0.7574	0.5426	0.9125	0.028*
O16	0.84885 (15)	0.45891 (8)	0.94636 (17)	0.0215 (4)
C17	0.8009 (2)	0.43394 (11)	1.0383 (3)	0.0229 (5)
H17A	0.7174	0.4381	0.9943	0.027*
H17B	0.8286	0.4601	1.1265	0.027*
C18	0.8337 (2)	0.36153 (11)	1.0704 (3)	0.0207 (5)
H18A	0.9168	0.3574	1.1002	0.025*
H18B	0.8146	0.3474	1.1504	0.025*
C19	0.8310 (2)	0.29040 (11)	0.8733 (2)	0.0192 (5)
C20	0.9430 (2)	0.32263 (11)	0.8889 (2)	0.0180 (5)
H20A	0.9327	0.3714	0.8783	0.022*
H20B	1.0005	0.3135	0.9842	0.022*
N21	0.98335 (17)	0.29775 (9)	0.7851 (2)	0.0180 (4)
C22	0.9321 (2)	0.32465 (11)	0.6440 (2)	0.0195 (5)
H22A	0.8500	0.3144	0.6043	0.023*
H22B	0.9664	0.3031	0.5838	0.023*
C23	0.9485 (2)	0.40027 (12)	0.6426 (2)	0.0197 (5)
C24	1.2164 (2)	0.29981 (11)	0.9071 (3)	0.0189 (5)
C25	1.2716 (2)	0.30417 (12)	1.0509 (3)	0.0219 (5)
H25	1.2430	0.2814	1.1107	0.026*
C26	1.3687 (2)	0.34197 (12)	1.1071 (3)	0.0251 (6)
H26	1.4071	0.3450	1.2063	0.030*
C27	1.4114 (2)	0.37568 (12)	1.0212 (3)	0.0254 (6)
C28	1.3541 (2)	0.37067 (12)	0.8774 (3)	0.0278 (6)
H28	1.3826	0.3936	0.8176	0.033*
C29	1.2567 (2)	0.33334 (12)	0.8185 (3)	0.0238 (6)
H29	1.2180	0.3306	0.7193	0.029*
C30	1.5165 (2)	0.41723 (14)	1.0863 (3)	0.0348 (7)
H30A	1.5386	0.4349	1.0123	0.052*
H30B	1.5780	0.3897	1.1507	0.052*
H30C	1.5014	0.4542	1.1385	0.052*

	U11	U22	U33	U12	U13	U23
S1	0.0290 (3)	0.0091 (3)	0.0181 (3)	0.0008 (2)	0.0132 (3)	−0.0004 (2)
O31	0.0373 (10)	0.0126 (8)	0.0184 (9)	0.0015 (7)	0.0160 (8)	−0.0042 (7)
O32	0.0362 (10)	0.0119 (8)	0.0200 (9)	0.0016 (7)	0.0155 (8)	0.0034 (7)
O33	0.0359 (10)	0.0133 (8)	0.0255 (10)	−0.0022 (7)	0.0158 (8)	−0.0042 (7)
O34	0.0326 (10)	0.0158 (9)	0.0217 (9)	−0.0019 (7)	0.0108 (8)	−0.0001 (7)
N1	0.0296 (11)	0.0125 (9)	0.0193 (11)	−0.0011 (8)	0.0143 (9)	−0.0009 (8)
C2	0.0327 (14)	0.0172 (12)	0.0270 (14)	0.0007 (10)	0.0186 (12)	0.0030 (10)
C3	0.0315 (14)	0.0138 (12)	0.0304 (14)	−0.0014 (10)	0.0188 (12)	−0.0003 (10)
O4	0.0329 (10)	0.0184 (9)	0.0236 (9)	−0.0005 (7)	0.0119 (8)	0.0039 (7)
C5	0.0305 (14)	0.0334 (15)	0.0270 (15)	−0.0026 (12)	0.0134 (12)	−0.0004 (12)
C6	0.0277 (14)	0.0426 (17)	0.0285 (15)	0.0059 (12)	0.0134 (12)	0.0094 (13)
O7	0.0289 (10)	0.0479 (13)	0.0237 (10)	−0.0007 (9)	0.0131 (8)	0.0017 (9)
C8	0.0320 (14)	0.0182 (12)	0.0228 (14)	0.0010 (10)	0.0119 (11)	0.0004 (10)
C9	0.0287 (13)	0.0159 (12)	0.0204 (13)	0.0017 (10)	0.0099 (11)	0.0023 (10)
N10	0.0296 (11)	0.0105 (9)	0.0223 (11)	0.0007 (8)	0.0127 (9)	0.0024 (8)
C11	0.0365 (15)	0.0117 (11)	0.0246 (14)	0.0013 (10)	0.0161 (12)	0.0053 (10)
C12	0.0400 (15)	0.0124 (11)	0.0245 (14)	0.0022 (10)	0.0168 (12)	0.0045 (10)
O13	0.0340 (10)	0.0158 (8)	0.0212 (9)	0.0001 (7)	0.0142 (8)	0.0000 (7)
C14	0.0351 (15)	0.0114 (11)	0.0267 (14)	−0.0007 (10)	0.0137 (12)	0.0016 (10)
C15	0.0405 (15)	0.0077 (11)	0.0252 (14)	−0.0001 (10)	0.0156 (12)	−0.0003 (9)
O16	0.0379 (10)	0.0083 (8)	0.0264 (10)	0.0010 (7)	0.0213 (8)	0.0004 (7)
C17	0.0378 (15)	0.0130 (11)	0.0265 (14)	−0.0007 (10)	0.0221 (12)	−0.0006 (10)
C18	0.0321 (14)	0.0152 (11)	0.0199 (13)	0.0001 (10)	0.0157 (11)	−0.0003 (9)
C19	0.0310 (14)	0.0102 (11)	0.0188 (13)	0.0041 (9)	0.0121 (11)	0.0042 (9)
C20	0.0285 (13)	0.0114 (11)	0.0177 (12)	0.0027 (9)	0.0129 (10)	0.0004 (9)
N21	0.0296 (11)	0.0134 (9)	0.0152 (10)	0.0022 (8)	0.0132 (9)	0.0014 (8)
C22	0.0311 (13)	0.0125 (11)	0.0167 (12)	0.0011 (9)	0.0112 (11)	−0.0005 (9)
C23	0.0340 (14)	0.0143 (11)	0.0165 (12)	0.0031 (10)	0.0162 (11)	0.0017 (9)
C24	0.0268 (13)	0.0113 (11)	0.0214 (13)	0.0034 (9)	0.0123 (11)	0.0001 (9)
C25	0.0301 (14)	0.0159 (12)	0.0225 (13)	0.0032 (10)	0.0134 (11)	0.0007 (10)
C26	0.0335 (14)	0.0186 (12)	0.0242 (14)	0.0028 (11)	0.0124 (12)	0.0008 (10)
C27	0.0294 (14)	0.0155 (12)	0.0326 (15)	0.0022 (10)	0.0136 (12)	−0.0038 (11)
C28	0.0378 (15)	0.0202 (13)	0.0333 (16)	−0.0015 (11)	0.0225 (13)	0.0001 (11)
C29	0.0339 (14)	0.0193 (12)	0.0224 (13)	0.0002 (10)	0.0155 (12)	−0.0005 (10)
C30	0.0361 (16)	0.0299 (15)	0.0413 (18)	−0.0059 (12)	0.0181 (14)	−0.0068 (13)

S1—O32	1.4295 (16)	C12—H12B	0.9900
S1—O31	1.4308 (16)	O13—C14	1.412 (3)
S1—N21	1.608 (2)	C14—C15	1.486 (3)
S1—C24	1.763 (2)	C14—H14A	0.9900
O33—C19	1.226 (3)	C14—H14B	0.9900
O34—C23	1.220 (3)	C15—O16	1.433 (3)
N1—C19	1.349 (3)	C15—H15A	0.9900
N1—C2	1.465 (3)	C15—H15B	0.9900
N1—C18	1.467 (3)	O16—C17	1.408 (3)
C2—C3	1.502 (4)	C17—C18	1.515 (3)
C2—H2A	0.9900	C17—H17A	0.9900
C2—H2B	0.9900	C17—H17B	0.9900
C3—O4	1.418 (3)	C18—H18A	0.9900
C3—H3A	0.9900	C18—H18B	0.9900
C3—H3B	0.9900	C19—C20	1.523 (3)
O4—C5	1.406 (3)	C20—N21	1.449 (3)
C5—C6	1.505 (4)	C20—H20A	0.9900
C5—H5A	0.9900	C20—H20B	0.9900
C5—H5B	0.9900	N21—C22	1.450 (3)
C6—O7	1.421 (3)	C22—C23	1.535 (3)
C6—H6A	0.9900	C22—H22A	0.9900
C6—H6B	0.9900	C22—H22B	0.9900
O7—C8	1.410 (3)	C24—C25	1.377 (3)
C8—C9	1.523 (3)	C24—C29	1.388 (3)
C8—H8A	0.9900	C25—C26	1.378 (4)
C8—H8B	0.9900	C25—H25	0.9500
C9—N10	1.463 (3)	C26—C27	1.386 (4)
C9—H9A	0.9900	C26—H26	0.9500
C9—H9B	0.9900	C27—C28	1.380 (4)
N10—C23	1.349 (3)	C27—C30	1.502 (4)
N10—C11	1.470 (3)	C28—C29	1.377 (4)
C11—C12	1.516 (3)	C28—H28	0.9500
C11—H11A	0.9900	C29—H29	0.9500
C11—H11B	0.9900	C30—H30A	0.9800
C12—O13	1.414 (3)	C30—H30B	0.9800
C12—H12A	0.9900	C30—H30C	0.9800
O32—S1—O31	119.36 (10)	C15—C14—H14B	110.1
O32—S1—N21	107.27 (10)	H14A—C14—H14B	108.4
O31—S1—N21	106.89 (10)	O16—C15—C14	108.70 (19)
O32—S1—C24	107.00 (11)	O16—C15—H15A	109.9
O31—S1—C24	106.83 (11)	C14—C15—H15A	109.9
N21—S1—C24	109.24 (11)	O16—C15—H15B	109.9
C19—N1—C2	120.8 (2)	C14—C15—H15B	109.9
C19—N1—C18	123.1 (2)	H15A—C15—H15B	108.3
C2—N1—C18	114.95 (19)	C17—O16—C15	111.61 (17)
N1—C2—C3	117.4 (2)	O16—C17—C18	109.52 (19)
N1—C2—H2A	108.0	O16—C17—H17A	109.8
C3—C2—H2A	108.0	C18—C17—H17A	109.8
N1—C2—H2B	108.0	O16—C17—H17B	109.8
C3—C2—H2B	108.0	C18—C17—H17B	109.8
H2A—C2—H2B	107.2	H17A—C17—H17B	108.2
O4—C3—C2	110.3 (2)	N1—C18—C17	114.2 (2)
O4—C3—H3A	109.6	N1—C18—H18A	108.7
C2—C3—H3A	109.6	C17—C18—H18A	108.7
O4—C3—H3B	109.6	N1—C18—H18B	108.7
C2—C3—H3B	109.6	C17—C18—H18B	108.7
H3A—C3—H3B	108.1	H18A—C18—H18B	107.6
C5—O4—C3	111.67 (19)	O33—C19—N1	122.5 (2)
O4—C5—C6	110.2 (2)	O33—C19—C20	120.9 (2)
O4—C5—H5A	109.6	N1—C19—C20	116.5 (2)
C6—C5—H5A	109.6	N21—C20—C19	111.60 (19)
O4—C5—H5B	109.6	N21—C20—H20A	109.3
C6—C5—H5B	109.6	C19—C20—H20A	109.3
H5A—C5—H5B	108.1	N21—C20—H20B	109.3
O7—C6—C5	113.4 (2)	C19—C20—H20B	109.3
O7—C6—H6A	108.9	H20A—C20—H20B	108.0
C5—C6—H6A	108.9	C20—N21—C22	117.56 (18)
O7—C6—H6B	108.9	C20—N21—S1	119.35 (16)
C5—C6—H6B	108.9	C22—N21—S1	122.47 (16)
H6A—C6—H6B	107.7	N21—C22—C23	111.63 (19)
C8—O7—C6	113.3 (2)	N21—C22—H22A	109.3
O7—C8—C9	108.1 (2)	C23—C22—H22A	109.3
O7—C8—H8A	110.1	N21—C22—H22B	109.3
C9—C8—H8A	110.1	C23—C22—H22B	109.3
O7—C8—H8B	110.1	H22A—C22—H22B	108.0
C9—C8—H8B	110.1	O34—C23—N10	123.5 (2)
H8A—C8—H8B	108.4	O34—C23—C22	118.9 (2)
N10—C9—C8	111.4 (2)	N10—C23—C22	117.5 (2)
N10—C9—H9A	109.3	C25—C24—C29	120.9 (2)
C8—C9—H9A	109.3	C25—C24—S1	119.50 (19)
N10—C9—H9B	109.3	C29—C24—S1	119.57 (19)
C8—C9—H9B	109.3	C24—C25—C26	119.3 (2)
H9A—C9—H9B	108.0	C24—C25—H25	120.4
C23—N10—C9	124.1 (2)	C26—C25—H25	120.4
C23—N10—C11	118.7 (2)	C25—C26—C27	121.1 (2)
C9—N10—C11	117.10 (19)	C25—C26—H26	119.5
N10—C11—C12	113.9 (2)	C27—C26—H26	119.5
N10—C11—H11A	108.8	C28—C27—C26	118.5 (2)
C12—C11—H11A	108.8	C28—C27—C30	122.0 (2)
N10—C11—H11B	108.8	C26—C27—C30	119.6 (2)
C12—C11—H11B	108.8	C29—C28—C27	121.7 (2)
H11A—C11—H11B	107.7	C29—C28—H28	119.2
O13—C12—C11	114.7 (2)	C27—C28—H28	119.2
O13—C12—H12A	108.6	C28—C29—C24	118.6 (2)
C11—C12—H12A	108.6	C28—C29—H29	120.7
O13—C12—H12B	108.6	C24—C29—H29	120.7
C11—C12—H12B	108.6	C27—C30—H30A	109.5
H12A—C12—H12B	107.6	C27—C30—H30B	109.5
C14—O13—C12	115.17 (19)	H30A—C30—H30B	109.5
O13—C14—C15	108.1 (2)	C27—C30—H30C	109.5
O13—C14—H14A	110.1	H30A—C30—H30C	109.5
C15—C14—H14A	110.1	H30B—C30—H30C	109.5
O13—C14—H14B	110.1
C19—N1—C2—C3	−49.0 (3)	O32—S1—N21—C20	36.3 (2)
C18—N1—C2—C3	142.7 (2)	O31—S1—N21—C20	165.43 (17)
N1—C2—C3—O4	−51.6 (3)	C24—S1—N21—C20	−79.33 (19)
C2—C3—O4—C5	−178.5 (2)	O32—S1—N21—C22	−152.89 (18)
C3—O4—C5—C6	−166.4 (2)	O31—S1—N21—C22	−23.8 (2)
O4—C5—C6—O7	78.8 (3)	C24—S1—N21—C22	91.5 (2)
C5—C6—O7—C8	−79.4 (3)	C20—N21—C22—C23	59.8 (3)
C6—O7—C8—C9	−165.6 (2)	S1—N21—C22—C23	−111.2 (2)
O7—C8—C9—N10	170.55 (19)	C9—N10—C23—O34	−175.5 (2)
C8—C9—N10—C23	79.0 (3)	C11—N10—C23—O34	1.3 (4)
C8—C9—N10—C11	−97.8 (2)	C9—N10—C23—C22	7.2 (3)
C23—N10—C11—C12	−121.6 (2)	C11—N10—C23—C22	−176.0 (2)
C9—N10—C11—C12	55.4 (3)	N21—C22—C23—O34	36.9 (3)
N10—C11—C12—O13	50.6 (3)	N21—C22—C23—N10	−145.7 (2)
C11—C12—O13—C14	68.8 (3)	O32—S1—C24—C25	−14.6 (2)
C12—O13—C14—C15	−178.22 (18)	O31—S1—C24—C25	−143.47 (19)
O13—C14—C15—O16	76.8 (2)	N21—S1—C24—C25	101.2 (2)
C14—C15—O16—C17	−168.7 (2)	O32—S1—C24—C29	164.98 (18)
C15—O16—C17—C18	−170.2 (2)	O31—S1—C24—C29	36.1 (2)
C19—N1—C18—C17	103.2 (3)	N21—S1—C24—C29	−79.2 (2)
C2—N1—C18—C17	−88.9 (2)	C29—C24—C25—C26	−0.5 (4)
O16—C17—C18—N1	−70.9 (3)	S1—C24—C25—C26	178.99 (18)
C2—N1—C19—O33	−0.6 (4)	C24—C25—C26—C27	0.2 (4)
C18—N1—C19—O33	166.6 (2)	C25—C26—C27—C28	0.1 (4)
C2—N1—C19—C20	178.53 (19)	C25—C26—C27—C30	179.1 (2)
C18—N1—C19—C20	−14.2 (3)	C26—C27—C28—C29	0.0 (4)
O33—C19—C20—N21	7.8 (3)	C30—C27—C28—C29	−178.9 (2)
N1—C19—C20—N21	−171.41 (19)	C27—C28—C29—C24	−0.4 (4)
C19—C20—N21—C22	79.0 (2)	C25—C24—C29—C28	0.7 (4)
C19—C20—N21—S1	−109.7 (2)	S1—C24—C29—C28	−178.89 (19)