research communications
Molecular and H-pyrano[3,2-c:5,6-c′]bis[2,1-benzothiazin]-7(9H)-one 6,6,8,8-tetroxide dimethylformamide monosolvate
of 5,9-dimethyl-5aV. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv 61077, Ukraine, bSSI "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60, Nauky Ave., Kharkiv 61001, Ukraine, cNational University of Pharmacy, 4 Valentynivska St., Kharkiv 61168, Ukraine, and dFar Eastern State Medical University, 35 Murav'eva-Amurskogo St., Khabarovsk, 680000, Russian Federation
*Correspondence e-mail: rybalka19969@gmail.com
The title molecule crystallizes as a dimethylformamide monosolvate, C19H14N2O6S2·C3H7NO. The molecule was expected to adopt mirror symmetry but slightly different conformational characteristics of the condensed benzothiazine ring lead to symmetry 1. In the crystal, molecules form two types of stacking dimers with distances of 3.464 (2) Å and 3.528 (2) Å between π-systems. As a result, columns extending parallel to [100] are formed, which are connected to intermediate dimethylformamide solvent molecules by C—H⋯O interactions.
CCDC reference: 1935426
1. Chemical context
Alkyl 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylates are highly reactive compounds (Ukrainets et al., 2007). They easily form the corresponding with primary and many secondary alkyl, aryl or hetarylamines and can be converted to 5,9-di-R-6,7,8-trioxodiquinolino [3,4-b; 3′,4′-e]-4H-pyrans in high yields through thermolysis (Ukrainets et al., 2000). The acylating ability is distinctly reduced in alkyl 1-R-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylates (Ukrainets et al., 2014). However, a similar heterocycle, 5,9-dimethyl-5H-pyrano [3,2-c:5,6-c′]bis[2,1]benzothiazin-7(9H)-one 6,6,8,8-tetroxide (I) was synthesized based on methyl 4-hydroxy-1-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate (Ukrainets et al., 2013). The molecular and crystal structures of its dimethylformamide solvate are reported in the present communication.
2. Structural commentary
Both thiazine rings adopt a twist-boat conformation (Fig. 1) with slightly different characteristics despite the formally mirror-symmetric molecular structure of (I) in the gas phase. The puckering parameters (Zefirov et al., 1990) are: S = 0.51, θ = 44.8°, Ψ = 28.9° for the C1–C2–C3–C4–N1–S1 ring (1) and S = 0.48, θ = 50.0°, Ψ = 22.8° for the C5–C6–C7–C8–N2–S2 ring (2). The S1 and C1 atoms deviate by 0.669 (2) and 0.207 (2) Å, respectively, from the mean-square plane of the remaining atoms in ring (1). The corresponding deviations in ring (2) are 0.668 (2) and 0.270 (2) Å, respectively.
The 4H-pyran-4-one ring (3) adopts a sofa conformation with puckering parameters S = 0.14, θ = 24.7°, Ψ = 22.6°. The deviation of C19 from the plane of the remaining atoms of (3) is 0.087 (2) Å. The C1=C2 and C5=C6 bonds [1.3571 (17) Å and 1.3529 (17) Å] are slightly elongated as compared to the mean value of 1.329 Å for a Csp2=Csp2 bond (Bürgi & Dunitz, 1994).
The molecule also contains shortened contacts (the H⋯O van der Waals radii sum is 2.46 Å; Zefirov, 1997), which can be considered as attractive intramolecular interactions. However, the values of the corresponding C—H⋯O angles for the pairs C17⋯O3, C18⋯O5, C3A⋯O1A, C12⋯O1, C16⋯O1 (Table 1) are too small to allow them to be characterized as intramolecular hydrogen bonds.
A further analysis of the molecular structure revealed the presence of other shortened intramolecular contacts: H9⋯H17C = 2.21 Å (expected 2.34 Å), H13⋯H18B = 2.28 Å (expected 2.34 Å), H13⋯H18C = 2.31 Å (expected 2.34 Å). These shortened contacts affect the very small pyramidalization of the nitrogen atoms; the sums of the bond angles centered at the N1 and N2 atoms are 354 and 356°, respectively.
3. Supramolecular features
In the crystal, molecules of (I) form columns extending parallel to [100] whereby centrosymmetric pairs of molecules within a column interact by π–π stacking interactions (Fig. 2). The plane-to-plane distances between the π-systems in the centrosymmetric dimers are 3.464 (2) and 3.528 (2) Å. The mean-square plane was calculated for O1 and all carbon atoms (with the exception of C19) of the polycyclic entity.
The dimethylformamide solvent molecules are situated between the columns (Fig. 3) and are bound by weak intermolecular hydrogen bonds including C9—H9⋯O1Ai and C18—H18B⋯O1Aii (Table 2).
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4. Database survey
A search of the Cambridge Structural Database (Version 5.38, update February 2019; Groom et al., 2016) for the benzothiazine skeleton revealed 34 hits. In all structures, the conformation of the benzothiazine fragment is similar.
The title compound may be considered as a structural analogue of 5,9-diethyl-6,7,8-trioxodiquinolino[3,4-b;3′,4′-e]-4H-pyran (Ukrainets et al., 2000) with the carbonyl groups being replaced by sulfonyl groups.
5. Synthesis and crystallization
A mixture of methyl 4-hydroxy-1-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate (2.69 g, 0.01 mol) and diphenyl oxide (10 ml) was maintained on a metal bath at 493 K for 3 h, then cooled and diluted with ethanol (Fig. 4). The precipitate was filtered off, washed with ethanol, and recrystallized from DMF. 1.86 g (37% yield) of a colourless substance were obtained, including yellowish crystals of the title solvate; m.p. 640–642 K (decomp.).
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms were located from difference-Fourier maps. They were included in calculated positions and treated as riding with C—H = 0.96 Å, Uiso(H) = 1.5Ueq(C) for methyl groups and with C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C) for all other hydrogen atoms.
details are summarized in Table 2Supporting information
CCDC reference: 1935426
https://doi.org/10.1107/S2056989019008788/wm5508sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019008788/wm5508Isup2.hkl
Data collection: CrysAlis CCD (Agilent, 2012); cell
CrysAlis RED (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C19H14N2O6S2·C3H7NO | F(000) = 1048 |
Mr = 503.54 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2678 (2) Å | Cell parameters from 8803 reflections |
b = 26.5667 (7) Å | θ = 3.3–32.1° |
c = 11.3590 (3) Å | µ = 0.30 mm−1 |
β = 90.498 (3)° | T = 293 K |
V = 2193.13 (10) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.20 × 0.18 mm |
Agilent Xcalibur, Sapphire3 diffractometer | 6370 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5409 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 30.0°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −9→10 |
Tmin = 0.840, Tmax = 1.000 | k = −34→37 |
21958 measured reflections | l = −15→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.5564P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
6370 reflections | Δρmax = 0.31 e Å−3 |
311 parameters | Δρmin = −0.35 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.27857 (5) | 0.53088 (2) | 0.78395 (3) | 0.03522 (10) | |
S2 | 0.35468 (5) | 0.68735 (2) | 0.47772 (3) | 0.03406 (9) | |
N1 | 0.31960 (18) | 0.47039 (5) | 0.76567 (10) | 0.0355 (3) | |
N2 | 0.40095 (19) | 0.68763 (4) | 0.33637 (11) | 0.0377 (3) | |
O1 | 0.27500 (14) | 0.54076 (3) | 0.43723 (8) | 0.0300 (2) | |
O2 | 0.33446 (19) | 0.63741 (4) | 0.71036 (9) | 0.0475 (3) | |
O3 | 0.4170 (2) | 0.54940 (5) | 0.86153 (10) | 0.0556 (3) | |
O4 | 0.09057 (19) | 0.53887 (5) | 0.81476 (11) | 0.0528 (3) | |
O5 | 0.50923 (18) | 0.70840 (4) | 0.53734 (11) | 0.0511 (3) | |
O6 | 0.18001 (18) | 0.70953 (5) | 0.50021 (12) | 0.0529 (3) | |
C1 | 0.30950 (19) | 0.55350 (5) | 0.64196 (11) | 0.0294 (3) | |
C2 | 0.27719 (17) | 0.52260 (5) | 0.54891 (11) | 0.0274 (2) | |
C3 | 0.23924 (18) | 0.46944 (5) | 0.55627 (12) | 0.0287 (2) | |
C4 | 0.25669 (18) | 0.44458 (5) | 0.66557 (12) | 0.0307 (3) | |
C5 | 0.33905 (18) | 0.62303 (5) | 0.50507 (11) | 0.0288 (2) | |
C6 | 0.30000 (17) | 0.59081 (5) | 0.41606 (11) | 0.0271 (2) | |
C7 | 0.27399 (18) | 0.60439 (5) | 0.29458 (11) | 0.0293 (3) | |
C8 | 0.31990 (19) | 0.65325 (5) | 0.25751 (12) | 0.0330 (3) | |
C9 | 0.2198 (2) | 0.39295 (5) | 0.67129 (15) | 0.0388 (3) | |
H9 | 0.230327 | 0.375995 | 0.742662 | 0.047* | |
C10 | 0.1678 (2) | 0.36734 (6) | 0.57123 (16) | 0.0447 (4) | |
H10 | 0.144752 | 0.332967 | 0.575848 | 0.054* | |
C11 | 0.1491 (2) | 0.39142 (6) | 0.46392 (16) | 0.0445 (4) | |
H11 | 0.112482 | 0.373420 | 0.397521 | 0.053* | |
C12 | 0.1849 (2) | 0.44209 (5) | 0.45585 (13) | 0.0366 (3) | |
H12 | 0.173175 | 0.458353 | 0.383672 | 0.044* | |
C13 | 0.2965 (2) | 0.66588 (7) | 0.13887 (14) | 0.0450 (4) | |
H13 | 0.327636 | 0.697916 | 0.112718 | 0.054* | |
C14 | 0.2274 (2) | 0.63092 (8) | 0.06068 (14) | 0.0489 (4) | |
H14 | 0.213819 | 0.639567 | −0.018251 | 0.059* | |
C15 | 0.1778 (2) | 0.58326 (7) | 0.09716 (13) | 0.0443 (4) | |
H15 | 0.128749 | 0.560360 | 0.043496 | 0.053* | |
C16 | 0.2012 (2) | 0.56987 (6) | 0.21301 (12) | 0.0363 (3) | |
H16 | 0.168641 | 0.537724 | 0.237646 | 0.044* | |
C17 | 0.3401 (2) | 0.44312 (7) | 0.87830 (14) | 0.0449 (4) | |
H17C | 0.418161 | 0.414374 | 0.867349 | 0.067* | |
H17B | 0.221431 | 0.432194 | 0.904561 | 0.067* | |
H17A | 0.394062 | 0.465053 | 0.936211 | 0.067* | |
C18 | 0.4721 (3) | 0.73589 (7) | 0.29163 (18) | 0.0593 (5) | |
H18C | 0.371718 | 0.755881 | 0.262233 | 0.089* | |
H18B | 0.557380 | 0.729589 | 0.229276 | 0.089* | |
H18A | 0.533497 | 0.753615 | 0.354267 | 0.089* | |
C19 | 0.3323 (2) | 0.60783 (5) | 0.62857 (11) | 0.0317 (3) | |
N1A | 0.8356 (2) | 0.81500 (6) | 0.40202 (13) | 0.0473 (3) | |
O1A | 0.7557 (2) | 0.81809 (6) | 0.59460 (13) | 0.0654 (4) | |
C1A | 0.8365 (3) | 0.79886 (7) | 0.51263 (17) | 0.0503 (4) | |
H1A | 0.905307 | 0.770158 | 0.529054 | 0.060* | |
C2A | 0.9428 (3) | 0.79092 (10) | 0.3113 (2) | 0.0696 (6) | |
H2AC | 1.005000 | 0.762143 | 0.343706 | 0.104* | |
H2AB | 1.031860 | 0.814287 | 0.281574 | 0.104* | |
H2AA | 0.862751 | 0.780360 | 0.248316 | 0.104* | |
C3A | 0.7312 (4) | 0.85925 (9) | 0.3696 (2) | 0.0769 (7) | |
H3AC | 0.669591 | 0.853504 | 0.295690 | 0.115* | |
H3AB | 0.812776 | 0.887473 | 0.362385 | 0.115* | |
H3AA | 0.641725 | 0.866160 | 0.429150 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0477 (2) | 0.03408 (17) | 0.02385 (16) | −0.00072 (14) | −0.00252 (13) | −0.00174 (12) |
S2 | 0.04352 (19) | 0.02353 (15) | 0.03518 (18) | 0.00017 (12) | 0.00303 (14) | −0.00355 (12) |
N1 | 0.0438 (7) | 0.0324 (6) | 0.0301 (6) | 0.0006 (5) | −0.0039 (5) | 0.0038 (5) |
N2 | 0.0502 (7) | 0.0283 (6) | 0.0346 (6) | −0.0031 (5) | 0.0049 (5) | 0.0021 (5) |
O1 | 0.0424 (5) | 0.0251 (4) | 0.0226 (4) | −0.0028 (4) | 0.0001 (4) | −0.0031 (3) |
O2 | 0.0785 (9) | 0.0336 (5) | 0.0304 (5) | 0.0003 (5) | −0.0047 (5) | −0.0108 (4) |
O3 | 0.0812 (9) | 0.0509 (7) | 0.0343 (6) | −0.0151 (6) | −0.0219 (6) | 0.0006 (5) |
O4 | 0.0595 (8) | 0.0560 (7) | 0.0431 (6) | 0.0114 (6) | 0.0164 (5) | 0.0001 (5) |
O5 | 0.0641 (8) | 0.0393 (6) | 0.0499 (7) | −0.0184 (5) | −0.0046 (6) | −0.0075 (5) |
O6 | 0.0597 (8) | 0.0381 (6) | 0.0612 (8) | 0.0165 (5) | 0.0154 (6) | −0.0003 (5) |
C1 | 0.0363 (6) | 0.0282 (6) | 0.0237 (6) | 0.0000 (5) | −0.0018 (5) | −0.0020 (5) |
C2 | 0.0298 (6) | 0.0271 (6) | 0.0252 (6) | 0.0003 (5) | 0.0001 (4) | −0.0020 (4) |
C3 | 0.0291 (6) | 0.0258 (6) | 0.0313 (6) | 0.0002 (4) | 0.0005 (5) | −0.0028 (5) |
C4 | 0.0280 (6) | 0.0288 (6) | 0.0352 (7) | 0.0016 (5) | 0.0024 (5) | −0.0003 (5) |
C5 | 0.0336 (6) | 0.0251 (5) | 0.0276 (6) | 0.0004 (5) | 0.0001 (5) | −0.0025 (5) |
C6 | 0.0296 (6) | 0.0257 (6) | 0.0261 (6) | −0.0006 (4) | 0.0012 (4) | −0.0018 (4) |
C7 | 0.0304 (6) | 0.0332 (6) | 0.0244 (6) | 0.0023 (5) | 0.0008 (5) | −0.0015 (5) |
C8 | 0.0354 (7) | 0.0326 (6) | 0.0311 (6) | 0.0048 (5) | 0.0017 (5) | 0.0021 (5) |
C9 | 0.0379 (7) | 0.0301 (7) | 0.0483 (8) | 0.0004 (5) | 0.0049 (6) | 0.0069 (6) |
C10 | 0.0441 (8) | 0.0268 (6) | 0.0634 (10) | −0.0044 (6) | 0.0050 (7) | −0.0016 (7) |
C11 | 0.0494 (9) | 0.0331 (7) | 0.0508 (9) | −0.0058 (6) | −0.0023 (7) | −0.0128 (7) |
C12 | 0.0425 (8) | 0.0310 (7) | 0.0363 (7) | −0.0025 (6) | −0.0033 (6) | −0.0065 (5) |
C13 | 0.0552 (9) | 0.0445 (8) | 0.0352 (8) | 0.0084 (7) | 0.0007 (7) | 0.0103 (6) |
C14 | 0.0537 (10) | 0.0648 (11) | 0.0281 (7) | 0.0108 (8) | −0.0033 (6) | 0.0066 (7) |
C15 | 0.0423 (8) | 0.0628 (10) | 0.0278 (7) | 0.0007 (7) | −0.0038 (6) | −0.0071 (7) |
C16 | 0.0382 (7) | 0.0431 (8) | 0.0277 (6) | −0.0032 (6) | 0.0003 (5) | −0.0058 (6) |
C17 | 0.0520 (9) | 0.0474 (9) | 0.0352 (8) | 0.0035 (7) | −0.0022 (7) | 0.0127 (7) |
C18 | 0.0867 (14) | 0.0381 (9) | 0.0533 (11) | −0.0154 (9) | 0.0146 (10) | 0.0071 (8) |
C19 | 0.0398 (7) | 0.0281 (6) | 0.0273 (6) | 0.0003 (5) | −0.0030 (5) | −0.0042 (5) |
N1A | 0.0451 (7) | 0.0465 (8) | 0.0501 (8) | 0.0034 (6) | −0.0014 (6) | 0.0010 (6) |
O1A | 0.0776 (10) | 0.0597 (8) | 0.0593 (8) | −0.0037 (7) | 0.0145 (7) | −0.0117 (7) |
C1A | 0.0513 (10) | 0.0458 (9) | 0.0539 (10) | 0.0012 (7) | 0.0039 (8) | 0.0010 (8) |
C2A | 0.0693 (13) | 0.0796 (15) | 0.0602 (12) | 0.0119 (11) | 0.0173 (10) | 0.0069 (11) |
C3A | 0.0933 (18) | 0.0628 (13) | 0.0744 (15) | 0.0251 (12) | −0.0108 (13) | 0.0045 (11) |
S1—O3 | 1.4197 (12) | C10—C11 | 1.382 (2) |
S1—O4 | 1.4292 (14) | C10—H10 | 0.9300 |
S1—N1 | 1.6479 (13) | C11—C12 | 1.374 (2) |
S1—C1 | 1.7375 (13) | C11—H11 | 0.9300 |
S2—O5 | 1.4212 (12) | C12—H12 | 0.9300 |
S2—O6 | 1.4247 (12) | C13—C14 | 1.377 (3) |
S2—N2 | 1.6433 (13) | C13—H13 | 0.9300 |
S2—C5 | 1.7405 (13) | C14—C15 | 1.381 (3) |
N1—C4 | 1.4012 (18) | C14—H14 | 0.9300 |
N1—C17 | 1.4767 (18) | C15—C16 | 1.372 (2) |
N2—C8 | 1.4052 (18) | C15—H15 | 0.9300 |
N2—C18 | 1.474 (2) | C16—H16 | 0.9300 |
O1—C2 | 1.3571 (15) | C17—H17C | 0.9600 |
O1—C6 | 1.3638 (15) | C17—H17B | 0.9600 |
O2—C19 | 1.2168 (16) | C17—H17A | 0.9600 |
C1—C2 | 1.3571 (17) | C18—H18C | 0.9600 |
C1—C19 | 1.4610 (18) | C18—H18B | 0.9600 |
C2—C3 | 1.4415 (17) | C18—H18A | 0.9600 |
C3—C12 | 1.4062 (18) | N1A—C1A | 1.328 (2) |
C3—C4 | 1.4110 (19) | N1A—C3A | 1.445 (3) |
C4—C9 | 1.3992 (19) | N1A—C2A | 1.446 (3) |
C5—C6 | 1.3529 (17) | O1A—C1A | 1.217 (2) |
C5—C19 | 1.4611 (18) | C1A—H1A | 0.9300 |
C6—C7 | 1.4371 (17) | C2A—H2AC | 0.9600 |
C7—C16 | 1.4039 (19) | C2A—H2AB | 0.9600 |
C7—C8 | 1.4055 (19) | C2A—H2AA | 0.9600 |
C8—C13 | 1.398 (2) | C3A—H3AC | 0.9600 |
C9—C10 | 1.375 (2) | C3A—H3AB | 0.9600 |
C9—H9 | 0.9300 | C3A—H3AA | 0.9600 |
O3—S1—O4 | 118.06 (9) | C12—C11—H11 | 120.2 |
O3—S1—N1 | 106.74 (7) | C10—C11—H11 | 120.2 |
O4—S1—N1 | 110.49 (7) | C11—C12—C3 | 120.27 (14) |
O3—S1—C1 | 111.08 (7) | C11—C12—H12 | 119.9 |
O4—S1—C1 | 107.92 (7) | C3—C12—H12 | 119.9 |
N1—S1—C1 | 101.26 (6) | C14—C13—C8 | 120.03 (16) |
O5—S2—O6 | 116.97 (8) | C14—C13—H13 | 120.0 |
O5—S2—N2 | 107.23 (7) | C8—C13—H13 | 120.0 |
O6—S2—N2 | 111.32 (8) | C13—C14—C15 | 121.31 (14) |
O5—S2—C5 | 110.72 (7) | C13—C14—H14 | 119.3 |
O6—S2—C5 | 108.33 (7) | C15—C14—H14 | 119.3 |
N2—S2—C5 | 101.13 (6) | C16—C15—C14 | 119.65 (15) |
C4—N1—C17 | 119.52 (12) | C16—C15—H15 | 120.2 |
C4—N1—S1 | 121.43 (9) | C14—C15—H15 | 120.2 |
C17—N1—S1 | 112.73 (10) | C15—C16—C7 | 120.43 (15) |
C8—N2—C18 | 119.46 (13) | C15—C16—H16 | 119.8 |
C8—N2—S2 | 122.12 (10) | C7—C16—H16 | 119.8 |
C18—N2—S2 | 114.59 (11) | N1—C17—H17C | 109.5 |
C2—O1—C6 | 120.73 (10) | N1—C17—H17B | 109.5 |
C2—C1—C19 | 122.37 (12) | H17C—C17—H17B | 109.5 |
C2—C1—S1 | 119.40 (10) | N1—C17—H17A | 109.5 |
C19—C1—S1 | 117.00 (9) | H17C—C17—H17A | 109.5 |
C1—C2—O1 | 120.90 (12) | H17B—C17—H17A | 109.5 |
C1—C2—C3 | 125.40 (12) | N2—C18—H18C | 109.5 |
O1—C2—C3 | 113.69 (11) | N2—C18—H18B | 109.5 |
C12—C3—C4 | 119.62 (12) | H18C—C18—H18B | 109.5 |
C12—C3—C2 | 120.78 (12) | N2—C18—H18A | 109.5 |
C4—C3—C2 | 119.60 (12) | H18C—C18—H18A | 109.5 |
C9—C4—N1 | 120.23 (13) | H18B—C18—H18A | 109.5 |
C9—C4—C3 | 118.95 (13) | O2—C19—C1 | 124.01 (13) |
N1—C4—C3 | 120.73 (12) | O2—C19—C5 | 123.66 (13) |
C6—C5—C19 | 122.28 (12) | C1—C19—C5 | 112.20 (11) |
C6—C5—S2 | 120.08 (10) | C1A—N1A—C3A | 120.13 (17) |
C19—C5—S2 | 116.45 (9) | C1A—N1A—C2A | 122.24 (17) |
C5—C6—O1 | 120.83 (11) | C3A—N1A—C2A | 117.58 (18) |
C5—C6—C7 | 125.71 (12) | O1A—C1A—N1A | 126.16 (19) |
O1—C6—C7 | 113.42 (11) | O1A—C1A—H1A | 116.9 |
C16—C7—C8 | 119.64 (12) | N1A—C1A—H1A | 116.9 |
C16—C7—C6 | 121.02 (12) | N1A—C2A—H2AC | 109.5 |
C8—C7—C6 | 119.33 (12) | N1A—C2A—H2AB | 109.5 |
C13—C8—N2 | 120.35 (14) | H2AC—C2A—H2AB | 109.5 |
C13—C8—C7 | 118.91 (13) | N1A—C2A—H2AA | 109.5 |
N2—C8—C7 | 120.57 (12) | H2AC—C2A—H2AA | 109.5 |
C10—C9—C4 | 119.88 (15) | H2AB—C2A—H2AA | 109.5 |
C10—C9—H9 | 120.1 | N1A—C3A—H3AC | 109.5 |
C4—C9—H9 | 120.1 | N1A—C3A—H3AB | 109.5 |
C9—C10—C11 | 121.62 (14) | H3AC—C3A—H3AB | 109.5 |
C9—C10—H10 | 119.2 | N1A—C3A—H3AA | 109.5 |
C11—C10—H10 | 119.2 | H3AC—C3A—H3AA | 109.5 |
C12—C11—C10 | 119.67 (14) | H3AB—C3A—H3AA | 109.5 |
O3—S1—N1—C4 | −156.20 (12) | C19—C5—C6—O1 | −8.4 (2) |
O4—S1—N1—C4 | 74.25 (13) | S2—C5—C6—O1 | −175.54 (9) |
C1—S1—N1—C4 | −39.91 (13) | C19—C5—C6—C7 | 169.19 (13) |
O3—S1—N1—C17 | 51.92 (13) | S2—C5—C6—C7 | 2.0 (2) |
O4—S1—N1—C17 | −77.63 (12) | C2—O1—C6—C5 | 4.20 (19) |
C1—S1—N1—C17 | 168.21 (11) | C2—O1—C6—C7 | −173.67 (11) |
O5—S2—N2—C8 | 154.03 (12) | C5—C6—C7—C16 | −168.18 (14) |
O6—S2—N2—C8 | −76.87 (13) | O1—C6—C7—C16 | 9.57 (18) |
C5—S2—N2—C8 | 38.02 (13) | C5—C6—C7—C8 | 10.9 (2) |
O5—S2—N2—C18 | −48.17 (15) | O1—C6—C7—C8 | −171.32 (12) |
O6—S2—N2—C18 | 80.93 (15) | C18—N2—C8—C13 | −3.9 (2) |
C5—S2—N2—C18 | −164.18 (13) | S2—N2—C8—C13 | 152.83 (12) |
O3—S1—C1—C2 | 141.18 (12) | C18—N2—C8—C7 | 171.24 (15) |
O4—S1—C1—C2 | −87.94 (13) | S2—N2—C8—C7 | −32.00 (19) |
N1—S1—C1—C2 | 28.13 (13) | C16—C7—C8—C13 | −1.8 (2) |
O3—S1—C1—C19 | −51.17 (13) | C6—C7—C8—C13 | 179.13 (13) |
O4—S1—C1—C19 | 79.71 (12) | C16—C7—C8—N2 | −176.99 (13) |
N1—S1—C1—C19 | −164.22 (11) | C6—C7—C8—N2 | 3.9 (2) |
C19—C1—C2—O1 | 3.8 (2) | N1—C4—C9—C10 | −176.42 (14) |
S1—C1—C2—O1 | 170.77 (10) | C3—C4—C9—C10 | 0.1 (2) |
C19—C1—C2—C3 | −174.90 (13) | C4—C9—C10—C11 | −0.6 (2) |
S1—C1—C2—C3 | −7.95 (19) | C9—C10—C11—C12 | 0.7 (3) |
C6—O1—C2—C1 | −1.91 (19) | C10—C11—C12—C3 | −0.4 (2) |
C6—O1—C2—C3 | 176.96 (11) | C4—C3—C12—C11 | −0.1 (2) |
C1—C2—C3—C12 | 171.94 (13) | C2—C3—C12—C11 | 179.99 (14) |
O1—C2—C3—C12 | −6.86 (18) | N2—C8—C13—C14 | 176.03 (15) |
C1—C2—C3—C4 | −8.0 (2) | C7—C8—C13—C14 | 0.8 (2) |
O1—C2—C3—C4 | 173.18 (11) | C8—C13—C14—C15 | 0.8 (3) |
C17—N1—C4—C9 | −2.2 (2) | C13—C14—C15—C16 | −1.4 (3) |
S1—N1—C4—C9 | −152.27 (12) | C14—C15—C16—C7 | 0.4 (2) |
C17—N1—C4—C3 | −178.74 (13) | C8—C7—C16—C15 | 1.2 (2) |
S1—N1—C4—C3 | 31.23 (18) | C6—C7—C16—C15 | −179.73 (14) |
C12—C3—C4—C9 | 0.2 (2) | C2—C1—C19—O2 | 168.80 (15) |
C2—C3—C4—C9 | −179.87 (13) | S1—C1—C19—O2 | 1.6 (2) |
C12—C3—C4—N1 | 176.72 (13) | C2—C1—C19—C5 | −7.13 (19) |
C2—C3—C4—N1 | −3.32 (19) | S1—C1—C19—C5 | −174.38 (10) |
O5—S2—C5—C6 | −136.55 (12) | C6—C5—C19—O2 | −166.55 (15) |
O6—S2—C5—C6 | 93.95 (13) | S2—C5—C19—O2 | 1.0 (2) |
N2—S2—C5—C6 | −23.15 (13) | C6—C5—C19—C1 | 9.40 (19) |
O5—S2—C5—C19 | 55.58 (13) | S2—C5—C19—C1 | 176.98 (10) |
O6—S2—C5—C19 | −73.91 (12) | C3A—N1A—C1A—O1A | −0.3 (3) |
N2—S2—C5—C19 | 168.99 (11) | C2A—N1A—C1A—O1A | 177.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17A···O3 | 0.96 | 2.40 | 2.885 (2) | 111 |
C18—H18A···O5 | 0.96 | 2.41 | 2.895 (2) | 111 |
C3A—H3AA···O1A | 0.96 | 2.41 | 2.784 (3) | 103 |
C12—H12···O1 | 0.93 | 2.39 | 2.7106 (17) | 100 |
C16—H16···O1 | 0.93 | 2.39 | 2.7109 (17) | 100 |
C9—H9···O1Ai | 0.93 | 2.41 | 3.324 (2) | 169 |
C18—H18B···O1Aii | 0.96 | 2.46 | 3.376 (3) | 159 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+3/2, z−1/2. |
Acknowledgements
Any acknowledgements?
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