Diethyl 2-[(1-methyl-1H-pyrrol-2-yl)methyl-ene-amino]-5-(2-thienylmethyl-ene-amino)thio-phene-3,4-dicarboxyl-ate.

Both imine bonds of the title compound, C(21)H(21)N(3)O(4)S(2), were found to be in the E configuration. The terminal pyrrole and thio-phene rings are twisted by 2.5 (3) and 2.3 (2)°, respectively, from the mean plane of the central thio-phene to which they are attached. The structure is disordered by exchange of the terminal heterocyclic rings; the site occupancy factors are ca 0.8 and 0.2. The crystal packing involves some π-π stacking [3.449 (4) Å between pyrrole and terminal thio-phene rings].

Related literature

For general background, see: Dufresne et al. (2007 ▶). For a similar compound, see: Dufresne et al. (2006 ▶).

Experimental

Crystal data

C21H21N3O4S2

M = 443.53

Monoclinic,

a = 30.7355 (14) Å

b = 6.9617 (4) Å

c = 19.5163 (9) Å

β = 92.732 (2)°

V = 4171.2 (4) Å3

Z = 8

Cu Kα radiation

μ = 2.60 mm−1

T = 150 (2) K

0.14 × 0.09 × 0.05 mm

Data collection

Bruker SMART 6K diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.712, T max = 0.881

24275 measured reflections

4076 independent reflections

3330 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.03

4076 reflections

394 parameters

544 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: UdMX (Marris, 2004 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053680800799X/fl2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800799X/fl2192Isup2.hkl

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

C21H21N3O4S2	F000 = 1856
Mr = 443.53	Dx = 1.413 Mg m−3
Monoclinic, C2/c	Cu Kα radiation λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 30.7355 (14) Å	θ = 15.0–30.0º
b = 6.9617 (4) Å	µ = 2.60 mm−1
c = 19.5163 (9) Å	T = 150 (2) K
β = 92.732 (2)º	Block, red
V = 4171.2 (4) Å3	0.14 × 0.09 × 0.05 mm
Z = 8

Bruker SMART 6K diffractometer	4076 independent reflections
Radiation source: Rotating Anode	3330 reflections with I > 2σ(I)
Monochromator: Montel 200 optics	Rint = 0.041
Detector resolution: 5.5 pixels mm-1	θmax = 71.9º
T = 150(2) K	θmin = 2.9º
ω scans	h = −37→36
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −7→8
Tmin = 0.712, Tmax = 0.881	l = −23→24
24275 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0781P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4076 reflections	Δρmax = 0.28 e Å−3
394 parameters	Δρmin = −0.38 e Å−3
544 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.10022 (4)	1.12212 (19)	0.84005 (7)	0.0407 (3)
O2	0.10797 (4)	0.80068 (19)	0.84277 (7)	0.0389 (3)
O3	0.17783 (4)	1.0055 (2)	0.75085 (6)	0.0409 (3)
O4	0.25038 (4)	1.00854 (18)	0.76690 (6)	0.0336 (3)
N1	0.12908 (5)	0.9423 (2)	0.99876 (7)	0.0313 (3)
N2	0.28368 (5)	1.0327 (2)	0.90462 (7)	0.0300 (3)
S2	0.219461 (14)	0.98751 (6)	0.99760 (2)	0.03223 (14)
C6	0.16602 (6)	0.9698 (2)	0.96274 (9)	0.0306 (4)
C7	0.16479 (6)	0.9824 (2)	0.89280 (9)	0.0298 (4)
C8	0.20672 (6)	1.0028 (2)	0.86477 (9)	0.0288 (4)
C9	0.24011 (6)	1.0096 (2)	0.91492 (8)	0.0290 (4)
C16	0.12129 (6)	0.9810 (3)	0.85451 (9)	0.0321 (4)
C17	0.06400 (6)	0.7790 (3)	0.81304 (11)	0.0482 (5)
H17A	0.0637	0.7996	0.7628	0.058*
H17B	0.0444	0.8747	0.8330	0.058*
C18	0.04913 (8)	0.5837 (4)	0.82806 (14)	0.0711 (8)
H18A	0.0697	0.4902	0.8105	0.107*
H18B	0.0202	0.5629	0.8060	0.107*
H18C	0.0476	0.5677	0.8778	0.107*
C19	0.20984 (6)	1.0069 (2)	0.78909 (9)	0.0302 (4)
C20	0.25276 (6)	1.0069 (3)	0.69247 (8)	0.0351 (4)
H20A	0.2385	1.1227	0.6724	0.042*
H20B	0.2379	0.8918	0.6729	0.042*
C21	0.30039 (6)	1.0039 (3)	0.67686 (10)	0.0399 (4)
H21A	0.3148	1.1182	0.6965	0.060*
H21B	0.3032	1.0032	0.6271	0.060*
H21C	0.3141	0.8884	0.6968	0.060*
S1	0.04126 (2)	0.87795 (11)	1.05416 (4)	0.0370 (3)	0.824 (3)
C1	0.01520 (10)	0.8382 (8)	1.1284 (2)	0.0404 (7)	0.824 (3)
H1	−0.0153	0.8193	1.1302	0.049*	0.824 (3)
C2	0.04307 (17)	0.8370 (10)	1.1840 (3)	0.0417 (10)	0.824 (3)
H2	0.0342	0.8170	1.2294	0.050*	0.824 (3)
C3	0.08692 (15)	0.8685 (7)	1.1675 (2)	0.0352 (8)	0.824 (3)
H3	0.1106	0.8741	1.2005	0.042*	0.824 (3)
C4	0.09117 (17)	0.8899 (18)	1.0984 (3)	0.0307 (6)	0.824 (3)
C5	0.1310 (4)	0.925 (5)	1.0640 (5)	0.0317 (7)	0.824 (3)
H5	0.1581	0.9349	1.0894	0.038*	0.824 (3)
C10	0.3117 (3)	1.0332 (16)	0.9566 (10)	0.0321 (10)	0.824 (3)
H10	0.3007	1.0101	1.0005	0.038*	0.824 (3)
C11	0.3573 (2)	1.065 (3)	0.9540 (3)	0.0333 (6)	0.824 (3)
C12	0.38669 (14)	1.0773 (7)	1.01056 (16)	0.0390 (7)	0.824 (3)
H12	0.3798	1.0662	1.0573	0.047*	0.824 (3)
C13	0.42795 (12)	1.1086 (7)	0.98639 (14)	0.0409 (7)	0.824 (3)
H13	0.4545	1.1207	1.0130	0.049*	0.824 (3)
C14	0.42238 (10)	1.1186 (6)	0.91597 (15)	0.0400 (7)	0.824 (3)
H14	0.4451	1.1407	0.8855	0.048*	0.824 (3)
N3	0.38014 (10)	1.0927 (4)	0.89645 (15)	0.0357 (6)	0.824 (3)
C15	0.36240 (9)	1.0926 (4)	0.82465 (15)	0.0449 (6)	0.824 (3)
H15A	0.3479	1.2155	0.8146	0.067*	0.824 (3)
H15B	0.3414	0.9877	0.8182	0.067*	0.824 (3)
H15C	0.3862	1.0747	0.7936	0.067*	0.824 (3)
S1'	0.37454 (15)	1.1247 (7)	0.8684 (3)	0.0464 (14)	0.176 (3)
C1'	0.4267 (4)	1.143 (3)	0.8980 (8)	0.0400 (9)	0.176 (3)
H1'	0.4507	1.1708	0.8707	0.048*	0.176 (3)
C2'	0.4294 (6)	1.113 (4)	0.9662 (8)	0.0407 (9)	0.176 (3)
H2'	0.4559	1.1263	0.9927	0.049*	0.176 (3)
C3'	0.3897 (7)	1.060 (4)	0.9958 (8)	0.0390 (9)	0.176 (3)
H3'	0.3874	1.0219	1.0421	0.047*	0.176 (3)
C4'	0.3551 (9)	1.072 (16)	0.9488 (14)	0.0333 (8)	0.176 (3)
C5'	0.128 (2)	0.92 (2)	1.064 (2)	0.0318 (9)	0.176 (3)
H5'	0.1560	0.9212	1.0873	0.038*	0.176 (3)
C10'	0.3104 (14)	1.053 (8)	0.957 (5)	0.0321 (11)	0.176 (3)
H10'	0.2995	1.0542	1.0014	0.039*	0.176 (3)
C11'	0.0926 (8)	0.881 (9)	1.1072 (13)	0.0307 (8)	0.176 (3)
C12'	0.0912 (8)	0.835 (4)	1.1755 (12)	0.0351 (9)	0.176 (3)
H12'	0.1155	0.8234	1.2073	0.042*	0.176 (3)
C13'	0.0477 (9)	0.809 (5)	1.1897 (12)	0.0416 (11)	0.176 (3)
H13'	0.0362	0.7884	1.2334	0.050*	0.176 (3)
C14'	0.0245 (6)	0.819 (4)	1.1278 (10)	0.0406 (9)	0.176 (3)
H14'	−0.0061	0.8035	1.1212	0.049*	0.176 (3)
N3'	0.0527 (4)	0.8565 (19)	1.0768 (6)	0.041 (3)	0.176 (3)
C15'	0.0380 (4)	0.8571 (17)	1.0042 (6)	0.040 (3)	0.176 (3)
H15D	0.0084	0.8052	0.9994	0.059*	0.176 (3)
H15E	0.0576	0.7776	0.9780	0.059*	0.176 (3)
H15F	0.0382	0.9890	0.9867	0.059*	0.176 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0392 (7)	0.0416 (8)	0.0411 (7)	0.0086 (6)	0.0006 (6)	0.0000 (6)
O2	0.0287 (7)	0.0390 (7)	0.0488 (8)	−0.0035 (5)	−0.0020 (6)	−0.0017 (6)
O3	0.0338 (7)	0.0578 (9)	0.0313 (7)	−0.0018 (6)	0.0021 (6)	−0.0045 (6)
O4	0.0316 (7)	0.0439 (7)	0.0256 (6)	−0.0015 (5)	0.0058 (5)	−0.0011 (5)
N1	0.0290 (8)	0.0329 (8)	0.0327 (8)	−0.0002 (6)	0.0090 (6)	−0.0012 (6)
N2	0.0288 (8)	0.0312 (8)	0.0302 (7)	−0.0012 (6)	0.0042 (6)	−0.0008 (6)
S2	0.0290 (2)	0.0407 (3)	0.0274 (2)	0.00037 (17)	0.00565 (17)	−0.00015 (17)
C6	0.0293 (9)	0.0304 (9)	0.0325 (9)	−0.0006 (7)	0.0052 (7)	−0.0023 (7)
C7	0.0303 (9)	0.0280 (9)	0.0316 (9)	0.0006 (7)	0.0049 (7)	−0.0006 (7)
C8	0.0294 (9)	0.0282 (9)	0.0292 (8)	0.0003 (6)	0.0057 (7)	−0.0026 (7)
C9	0.0301 (9)	0.0293 (9)	0.0280 (8)	0.0010 (6)	0.0061 (7)	−0.0011 (7)
C16	0.0298 (9)	0.0381 (10)	0.0289 (8)	−0.0020 (7)	0.0080 (7)	−0.0026 (7)
C17	0.0331 (10)	0.0482 (12)	0.0622 (13)	−0.0047 (9)	−0.0093 (9)	0.0014 (10)
C18	0.0580 (16)	0.0732 (18)	0.0798 (18)	−0.0287 (13)	−0.0214 (14)	0.0224 (14)
C19	0.0299 (9)	0.0297 (9)	0.0315 (9)	−0.0018 (7)	0.0046 (7)	−0.0013 (7)
C20	0.0407 (11)	0.0407 (10)	0.0243 (9)	−0.0030 (8)	0.0068 (7)	−0.0017 (7)
C21	0.0411 (11)	0.0450 (11)	0.0346 (10)	−0.0044 (8)	0.0112 (8)	−0.0025 (8)
S1	0.0284 (4)	0.0440 (4)	0.0388 (6)	−0.0025 (3)	0.0032 (3)	−0.0030 (3)
C1	0.0288 (16)	0.0424 (16)	0.0513 (11)	−0.0017 (15)	0.0147 (12)	−0.0097 (10)
C2	0.0397 (15)	0.046 (2)	0.0412 (13)	−0.0025 (14)	0.0167 (11)	−0.0029 (12)
C3	0.0323 (14)	0.039 (2)	0.0350 (15)	0.0005 (12)	0.0062 (10)	0.0008 (12)
C4	0.0291 (10)	0.0334 (15)	0.0299 (16)	−0.0004 (9)	0.0041 (10)	−0.0020 (18)
C5	0.027 (2)	0.0327 (10)	0.0354 (9)	0.000 (2)	0.0052 (10)	−0.0023 (7)
C10	0.0342 (11)	0.031 (3)	0.0311 (9)	0.0010 (13)	0.0056 (9)	0.001 (2)
C11	0.0328 (11)	0.0312 (11)	0.0360 (14)	0.0008 (12)	0.0025 (9)	0.000 (2)
C12	0.0371 (12)	0.0433 (15)	0.0364 (16)	0.0017 (10)	0.0007 (12)	−0.0064 (14)
C13	0.0331 (11)	0.0445 (12)	0.0444 (17)	−0.0007 (9)	−0.0045 (14)	−0.0032 (17)
C14	0.0296 (11)	0.0443 (15)	0.0469 (19)	−0.0015 (9)	0.0115 (11)	0.0047 (13)
N3	0.0340 (12)	0.0396 (14)	0.0336 (14)	0.0007 (9)	0.0031 (12)	0.0051 (11)
C15	0.0393 (14)	0.0672 (18)	0.0285 (14)	0.0014 (12)	0.0060 (11)	0.0073 (12)
S1'	0.036 (2)	0.054 (2)	0.051 (3)	−0.0032 (14)	0.011 (2)	0.002 (2)
C1'	0.0299 (14)	0.0443 (17)	0.047 (2)	−0.0016 (13)	0.0112 (14)	0.0045 (16)
C2'	0.0328 (13)	0.0445 (14)	0.044 (2)	−0.0007 (12)	−0.0038 (17)	−0.003 (2)
C3'	0.0372 (15)	0.0431 (17)	0.0367 (18)	0.0018 (13)	0.0010 (15)	−0.0061 (17)
C4'	0.0328 (13)	0.0312 (13)	0.0358 (16)	0.0009 (15)	0.0020 (12)	−0.001 (2)
C5'	0.028 (2)	0.0327 (13)	0.0353 (12)	0.000 (2)	0.0048 (13)	−0.0023 (11)
C10'	0.0341 (13)	0.031 (3)	0.0312 (12)	0.0011 (15)	0.0055 (12)	0.000 (2)
C11'	0.0288 (12)	0.0333 (17)	0.0303 (18)	−0.0003 (12)	0.0040 (13)	−0.002 (2)
C12'	0.0324 (16)	0.039 (2)	0.0349 (17)	0.0005 (15)	0.0064 (13)	0.0009 (15)
C13'	0.0397 (17)	0.045 (3)	0.0411 (15)	−0.0021 (16)	0.0160 (14)	−0.0028 (14)
C14'	0.0293 (19)	0.0423 (18)	0.0512 (14)	−0.0018 (17)	0.0142 (15)	−0.0094 (13)
N3'	0.041 (4)	0.041 (4)	0.040 (4)	0.001 (3)	−0.003 (3)	0.007 (3)
C15'	0.040 (5)	0.047 (6)	0.032 (6)	−0.005 (4)	−0.006 (4)	0.001 (4)

O1—C16	1.203 (2)	C5—H5	0.9500
O2—C16	1.337 (2)	C10—C11	1.423 (9)
O2—C17	1.453 (2)	C10—H10	0.9500
O3—C19	1.206 (2)	C11—N3	1.366 (5)
O4—C19	1.339 (2)	C11—C12	1.395 (5)
O4—C20	1.4578 (19)	C12—C13	1.391 (4)
N1—C5	1.278 (9)	C12—H12	0.9500
N1—C5'	1.28 (4)	C13—C14	1.379 (4)
N1—C6	1.377 (2)	C13—H13	0.9500
N2—C10'	1.28 (8)	C14—N3	1.347 (4)
N2—C10	1.299 (17)	C14—H14	0.9500
N2—C9	1.373 (2)	N3—C15	1.479 (3)
S2—C6	1.7519 (18)	C15—H15A	0.9800
S2—C9	1.7685 (16)	C15—H15B	0.9800
C6—C7	1.367 (2)	C15—H15C	0.9800
C7—C8	1.431 (2)	S1'—C1'	1.683 (14)
C7—C16	1.500 (2)	S1'—C4'	1.744 (16)
C8—C9	1.385 (2)	C1'—C2'	1.345 (14)
C8—C19	1.485 (2)	C1'—H1'	0.9500
C17—C18	1.468 (3)	C2'—C3'	1.422 (15)
C17—H17A	0.9900	C2'—H2'	0.9500
C17—H17B	0.9900	C3'—C4'	1.374 (17)
C18—H18A	0.9800	C3'—H3'	0.9500
C18—H18B	0.9800	C4'—C10'	1.40 (4)
C18—H18C	0.9800	C5'—C11'	1.44 (4)
C20—C21	1.509 (3)	C5'—H5'	0.9500
C20—H20A	0.9900	C10'—H10'	0.9500
C20—H20B	0.9900	C11'—N3'	1.348 (17)
C21—H21A	0.9800	C11'—C12'	1.374 (18)
C21—H21B	0.9800	C12'—C13'	1.391 (18)
C21—H21C	0.9800	C12'—H12'	0.9500
S1—C1	1.711 (4)	C13'—C14'	1.375 (18)
S1—C4	1.726 (4)	C13'—H13'	0.9500
C1—C2	1.350 (5)	C14'—N3'	1.375 (16)
C1—H1	0.9500	C14'—H14'	0.9500
C2—C3	1.418 (4)	N3'—C15'	1.467 (12)
C2—H2	0.9500	C15'—H15D	0.9800
C3—C4	1.368 (5)	C15'—H15E	0.9800
C3—H3	0.9500	C15'—H15F	0.9800
C4—C5	1.446 (9)
C16—O2—C17	115.94 (15)	N1—C5—C4	118.5 (10)
C19—O4—C20	114.46 (14)	N1—C5—H5	120.7
C5—N1—C6	121.4 (5)	C4—C5—H5	120.7
C5'—N1—C6	126 (3)	N2—C10—C11	126.2 (13)
C10'—N2—C9	119 (3)	N2—C10—H10	116.9
C10—N2—C9	120.1 (6)	C11—C10—H10	116.9
C6—S2—C9	91.28 (8)	N3—C11—C12	107.7 (4)
C7—C6—N1	122.32 (17)	N3—C11—C10	126.6 (9)
C7—C6—S2	111.36 (13)	C12—C11—C10	125.7 (9)
N1—C6—S2	126.31 (13)	C13—C12—C11	107.9 (3)
C6—C7—C8	113.93 (16)	C13—C12—H12	126.0
C6—C7—C16	118.61 (16)	C11—C12—H12	126.1
C8—C7—C16	127.42 (15)	C14—C13—C12	105.9 (3)
C9—C8—C7	112.57 (15)	C14—C13—H13	127.0
C9—C8—C19	128.43 (16)	C12—C13—H13	127.1
C7—C8—C19	118.96 (16)	N3—C14—C13	110.3 (3)
N2—C9—C8	126.55 (15)	N3—C14—H14	124.8
N2—C9—S2	122.60 (13)	C13—C14—H14	124.8
C8—C9—S2	110.85 (13)	C14—N3—C11	108.2 (3)
O1—C16—O2	124.72 (17)	C14—N3—C15	125.1 (3)
O1—C16—C7	124.68 (17)	C11—N3—C15	126.8 (3)
O2—C16—C7	110.46 (15)	C1'—S1'—C4'	94.0 (9)
O2—C17—C18	108.00 (17)	C2'—C1'—S1'	109.9 (11)
O2—C17—H17A	110.1	C2'—C1'—H1'	125.0
C18—C17—H17A	110.1	S1'—C1'—H1'	125.1
O2—C17—H17B	110.1	C1'—C2'—C3'	115.3 (14)
C18—C17—H17B	110.1	C1'—C2'—H2'	122.3
H17A—C17—H17B	108.4	C3'—C2'—H2'	122.3
C17—C18—H18A	109.5	C4'—C3'—C2'	111.5 (15)
C17—C18—H18B	109.5	C4'—C3'—H3'	124.3
H18A—C18—H18B	109.5	C2'—C3'—H3'	124.2
C17—C18—H18C	109.5	C3'—C4'—C10'	131 (4)
H18A—C18—H18C	109.5	C3'—C4'—S1'	108.9 (14)
H18B—C18—H18C	109.5	C10'—C4'—S1'	120 (4)
O3—C19—O4	122.97 (16)	N1—C5'—C11'	131 (5)
O3—C19—C8	121.73 (16)	N1—C5'—H5'	114.2
O4—C19—C8	115.29 (15)	C11'—C5'—H5'	114.3
O4—C20—C21	107.25 (15)	N2—C10'—C4'	121 (7)
O4—C20—H20A	110.3	N2—C10'—H10'	119.7
C21—C20—H20A	110.3	C4'—C10'—H10'	119.9
O4—C20—H20B	110.3	N3'—C11'—C12'	109.1 (17)
C21—C20—H20B	110.3	N3'—C11'—C5'	118 (3)
H20A—C20—H20B	108.5	C12'—C11'—C5'	132 (3)
C20—C21—H21A	109.5	C11'—C12'—C13'	107.3 (16)
C20—C21—H21B	109.5	C11'—C12'—H12'	126.4
H21A—C21—H21B	109.5	C13'—C12'—H12'	126.3
C20—C21—H21C	109.5	C14'—C13'—C12'	106.5 (16)
H21A—C21—H21C	109.5	C14'—C13'—H13'	126.8
H21B—C21—H21C	109.5	C12'—C13'—H13'	126.8
C1—S1—C4	91.4 (2)	N3'—C14'—C13'	109.0 (15)
C2—C1—S1	112.1 (3)	N3'—C14'—H14'	125.5
C2—C1—H1	123.9	C13'—C14'—H14'	125.5
S1—C1—H1	123.9	C11'—N3'—C14'	107.4 (14)
C1—C2—C3	113.0 (4)	C11'—N3'—C15'	131.1 (14)
C1—C2—H2	123.5	C14'—N3'—C15'	121.5 (13)
C3—C2—H2	123.5	N3'—C15'—H15D	109.5
C4—C3—C2	112.2 (4)	N3'—C15'—H15E	109.5
C4—C3—H3	123.9	H15D—C15'—H15E	109.5
C2—C3—H3	123.9	N3'—C15'—H15F	109.5
C3—C4—C5	126.8 (6)	H15D—C15'—H15F	109.5
C3—C4—S1	111.3 (3)	H15E—C15'—H15F	109.5
C5—C4—S1	121.9 (6)
C5—N1—C6—C7	177.8 (17)	C1—S1—C4—C3	−1.4 (8)
C5'—N1—C6—C7	175 (9)	C1—S1—C4—C5	−179.5 (18)
C5—N1—C6—S2	−0.6 (17)	C5'—N1—C5—C4	−27 (91)
C5'—N1—C6—S2	−3(9)	C6—N1—C5—C4	−177.9 (15)
C9—S2—C6—C7	−0.63 (13)	C3—C4—C5—N1	−179.7 (16)
C9—S2—C6—N1	177.95 (16)	S1—C4—C5—N1	−2(3)
N1—C6—C7—C8	−177.47 (15)	C9—N2—C10—C11	−176.7 (13)
S2—C6—C7—C8	1.18 (19)	N2—C10—C11—N3	−3(3)
N1—C6—C7—C16	4.7 (2)	N2—C10—C11—C12	175.7 (13)
S2—C6—C7—C16	−176.64 (12)	N3—C11—C12—C13	−1.3 (17)
C6—C7—C8—C9	−1.3 (2)	C10—C11—C12—C13	179.8 (16)
C16—C7—C8—C9	176.33 (16)	C11—C12—C13—C14	1.2 (11)
C6—C7—C8—C19	176.62 (15)	C12—C13—C14—N3	−0.7 (5)
C16—C7—C8—C19	−5.8 (3)	C13—C14—N3—C11	−0.1 (11)
C10'—N2—C9—C8	174 (3)	C13—C14—N3—C15	−179.4 (3)
C10—N2—C9—C8	−178.8 (6)	C12—C11—N3—C14	0.8 (16)
C10'—N2—C9—S2	−5(3)	C10—C11—N3—C14	179.7 (17)
C10—N2—C9—S2	2.1 (6)	C12—C11—N3—C15	−179.8 (7)
C7—C8—C9—N2	−178.42 (16)	C10—C11—N3—C15	−1(3)
C19—C8—C9—N2	4.0 (3)	C4'—S1'—C1'—C2'	−1(4)
C7—C8—C9—S2	0.73 (19)	S1'—C1'—C2'—C3'	4(3)
C19—C8—C9—S2	−176.89 (14)	C1'—C2'—C3'—C4'	−7(6)
C6—S2—C9—N2	179.12 (15)	C2'—C3'—C4'—C10'	−173 (9)
C6—S2—C9—C8	−0.07 (13)	C2'—C3'—C4'—S1'	6(8)
C17—O2—C16—O1	−2.7 (3)	C1'—S1'—C4'—C3'	−3(7)
C17—O2—C16—C7	173.15 (15)	C1'—S1'—C4'—C10'	176 (8)
C6—C7—C16—O1	90.3 (2)	C5—N1—C5'—C11'	151 (100)
C8—C7—C16—O1	−87.2 (2)	C6—N1—C5'—C11'	−178 (10)
C6—C7—C16—O2	−85.62 (19)	C9—N2—C10'—C4'	178 (6)
C8—C7—C16—O2	96.9 (2)	C3'—C4'—C10'—N2	−167 (8)
C16—O2—C17—C18	−158.52 (19)	S1'—C4'—C10'—N2	15 (11)
C20—O4—C19—O3	−0.5 (2)	N1—C5'—C11'—N3'	5(19)
C20—O4—C19—C8	178.27 (14)	N1—C5'—C11'—C12'	173 (10)
C9—C8—C19—O3	−177.86 (18)	N3'—C11'—C12'—C13'	−9(5)
C7—C8—C19—O3	4.7 (2)	C5'—C11'—C12'—C13'	−177 (10)
C9—C8—C19—O4	3.4 (2)	C11'—C12'—C13'—C14'	6(4)
C7—C8—C19—O4	−174.11 (15)	C12'—C13'—C14'—N3'	−2(4)
C19—O4—C20—C21	−178.59 (14)	C12'—C11'—N3'—C14'	8(5)
C4—S1—C1—C2	0.8 (6)	C5'—C11'—N3'—C14'	178 (8)
S1—C1—C2—C3	0.0 (7)	C12'—C11'—N3'—C15'	−170 (2)
C1—C2—C3—C4	−1.0 (9)	C5'—C11'—N3'—C15'	1(10)
C2—C3—C4—C5	179.6 (19)	C13'—C14'—N3'—C11'	−4(4)
C2—C3—C4—S1	1.6 (10)	C13'—C14'—N3'—C15'	174 (2)