research communications
Crystal structures of the H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one
of 2,3-diphenyl-2,3-dihydro-4aDepartment of Biochemistry and Molecular Biology Pennsylvania State University, University Park, PA 16802, USA, bDepartment of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA, cMendel Science Center, Villanova University, 800 Lancaster Avenue, Villanova, PA 19085, USA, and dPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
*Correspondence e-mail: ljs43@psu.edu
The title H-1,3-benzothiazine-1,1,4-trione, C20H15NO3S, and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazine-1,1,4-trione, C19H14N2O3S, crystallize in P21/n with two molecules in each of the asymmetric units and have almost identical unit cells and extended structures. In both structures, the thiazine rings exhibit a screw-boat pucker. The intermolecular interactions observed are C—H⋯O-type hydrogen bonds and parallel partial π–π stacking between the fused aromatic rings (benzo- or pyrido-) of the core of the molecules within each and also connecting to molecules with translational periodicity in the a-axis direction in what can be described as columns (two per asymmetric unit) of stacked molecules with alternating The pendant phenyl groups of both molecules do not participate in aromatic ring interactions.
2,3-diphenyl-2,3-dihydro-4Keywords: sulfone; 1,3-thiazin-4-one; screw-boat pucker; S-oxidation; crystal structure.
1. Chemical context
The 2,3-dihydro-4H-1,3-thiazin-4-ones are a group of six-membered heterocycles with a wide range of biological activity (Ryabukhin et al., 1996; Silverberg & Moyer, 2019). Surrey's research (Surrey et al., 1958, Surrey, 1963a,b) resulted in the discovery of two drugs, the antianxiety and muscle relaxant chlormezanone, 2-(4-chlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide (O'Neil, 2006; Tanaka & Hirayama, 2005) and the muscle relaxant dichlormezanone, 2-(3,4-dichlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide (Elks & Ganellin, 1990). These showed greater activity than the from which they were synthesized (Surrey et al., 1958).
Compounds in this group with a fused benzene or pyridine ring are of particular interest because of their potential biological activity (Silverberg et al., 2016, 2020, 2021; Malfara et al., 2021). We have previously reported the preparation of the title 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1,1-dioxide 1 and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one 1,1-dioxide 2 (Silverberg, 2020). We have also described the X-ray crystal structures of the corresponding 3 and 4 and 5 and 6 (Yennawar, Bendinsky et al., 2014; Yennawar, Singh et al., 2014; Yennawar, Fox et al., 2017; Yennawar, Noble et al., 2017). Herein we report the crystal structures of 1 and 2, along with a more complete characterization than previously reported (Silverberg, 2020).
2. Structural commentary
The two title compounds (Figs. 1 and 2) are structurally very similar with two molecules of each in the asymmetric units of the respective crystals. Both of the crystal structures are in the monoclinic P21/n with very similar unit-cell dimensions, and are fairly well superimposable (Fig. 3).
The structures of 1 and 2 both display a screw-boat (pucker) conformation for the four thiazine rings in the two asymmetric units [puckering amplitude Q ranging between 0.616 (4) and 0.6449 (16) Å, and the θ and φ values, after accounting for the absolute conformation transformations, are between 60.7 (4) and 63.02 (16)°, and 140.53 (18) and 142.9 (4)°, respectively]. The puckering observed is similar to that in the 5 and 6 (Yennawar, Fox et al. 2017; Yennawar, Noble et al. 2017), but is different from the envelope conformations seen in the 3 and 4 (Yennawar, Bendinsky et al., 2014; Yennawar, Singh et al., 2014). Each molecule contains one stereogenic center, which lies between the N atom and the SO2 group of the heterocyclic ring: in the of 1, C8 has an S configuration and C28 an R configuration, thus generating a racemic pair. The situation is 2 is similar, with C8 S and C28 R.
In compound 1, the dihedral angle between the substituent phenyl rings is 58.7 (2) and 57.4 (3)° in the two asymmetric molecules. Between the co-planar atoms of the fused benzene and the phenyl rings, the dihedral angle ranges between 83 and 100°. Compound 2 is again similar, showing a dihedral angle between the substituent phenyl rings of 53.04 (11) and 57.24 (13)°. Between the co-planar atoms of the pyridine ring and the phenyl rings of the respective structures, the dihedral angle ranges between 76 and 101°.
3. Supramolecular features
Both of the extended structures are consolidated by C—H⋯O hydrogen bonds (Tables 1 and 2). Assuming that the C—H⋯O angle should be greater than or equal to 130° as one of the qualifiers for such interactions, a very small variation in molecular positioning in the two structures results in two additional interactions for 2 as compared to that in 1. However, in both structures (starting from the interactions within the asymmetric units followed by translation periodicity along the a direction) intermolecular π–π stacking interactions between the fused aromatic rings, namely the benzene ring of the benzothiazine unit in 1 and the pyridine ring of the pyridothiazine unit in 2, can be seen (Figs. 4 and 5). The centroid–centroid separations in 1 are 3.522 (3) and 3.521 (3) Å with corresponding values of 3.5715 (15) and 3.5991 (15) Å in 2.
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4. Database survey
Searches were undertaken using the American Chemical Society's Chemical Abstract Service (CAS) Scifinder platform. Only two crystal structures of other H-1,3-benzothiazin-4-ones have been reported (Elghamry et al. 2007). No other sulfone of a 2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one has been synthesized.
of 2,3-dihydro-45. Synthesis and crystallization
TLC plates (silica gel GF, 250-micron, 10 × 20 cm, cat. No. 21521) were purchased from Analtech. TLCs were visualized under short-wave UV, and then with I2, and then by spraying with ceric ammonium nitrate/sulfuric acid and heating. Infrared spectra were run on a Thermo-Fisher NICOLET iS50 FT–IR using a diamond-ATR attachment for direct powder analysis (Penn State Schuylkill). 1H and 13C NMR experiments (Penn State's shared NMR facility, University Park) were carried out on a Bruker Advance-III-HD 500.20-MHz (1H frequency) instrument using a 5 mm Prodigy (liquid nitrogen cooled) BBO BB-1H/19F/D Z-GRD cryoprobe. Samples were dissolved in CDCl3 and analyzed at room temperature. Typical conditions for 1H acquisition were 2 s relaxation delay, acquisition time of 4.089 s, spectral width of 8 kHz, 16 scans. Spectra were zero-filled to 128k points, and multiplied by exponential multiplication (EM with LB = 0.3 Hz) prior to FT. For the 13C experiments, data were acquired with power-gated 1H decoupling using a 2 s relaxation delay, with acquisition time of 1.1 s, spectral width of 29.8 kHz, and 256 scans. Spectra were zero-filled once, and multiplied by EM with LB = 2 Hz prior to FT. The exact masses of the synthesized compounds were determined using LC–MS (Villanova University). Exact mass was measured on a SCIEX Exion LC with a SCIEX 5600+ TripleTOF MS. Separation was achieved on an Agilent Infinity LabPoroshell 120 EC-C18 column maintained at 40°C with a gradient of 90/10 (water/acetonitrile with 0.1% formic acid) ramped from 5/95 over 6 min at a flowrate of 0.5 ml min−1. The TOF–MS was scanned over 100–500 Da and calibrated with the SCIEX APCI positive calibrant solution prior to accurate Compound exact mass was measured in positive ESI mode with a DP = 100 V, CE = 10, GAS1 = GAS2 = 60 psi, CUR = 30 psi, ISV = 5500 V, and source temperature of 450°C. Melting points were performed on a Vernier Melt Station (Penn State Schuylkill).
General Oxidation Procedure (Surrey et al., 1958; Silverberg, 2020; Cannon et al., 2015): The heterocycle (0.267 mmol) was dissolved in glacial acetic acid (1.2 ml). An aqueous solution of KMnO4 (0.535 mmol in 1.45 ml water) was added dropwise at room temperature with vigorous stirring. The reaction was followed by TLC. Solid sodium bisulfite (NaHSO3/Na2S2O5) was added until the solution remained colorless; 1.45 ml of water was added and stirred for 10 min. The mixture was extracted with CH2Cl2 (3 × 5 ml). The organics were combined and washed once with sat. NaCl. The solution was dried over Na2SO4 and filtered. The product was purified by in a silica gel micro-column with mixtures of ethyl acetate and hexanes. Crystals for X-ray were grown as detailed below.
2,3-Diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1,1-dioxide, 1: Crystals for X-ray analysis were grown by slow evaporation from 2-propanol solution. 0.050 g (54%). m.p. 436–438 K. 1H NMR (CDCl3): δ(ppm): 8.29 (d, 1H, J = 7.7 Hz), 7.70 (m, 2H), 7.60 (t, J = 7.6 Hz, 1H), 7.32 (m, 2H), 7.25 (m, 8H), 5.79 (m, 1H, C2-H). 13C NMR (CDCl3) δ(ppm) 161.1 (C=O), 141.9, 135.0, 134.1, 133.4, 130.6, 130.0, 129.8, 129.1, 128.9, 128.6, 128.2, 126.6, 124.1, 82.6 (C2). HRMS (m/z): [M + H]+ of 350.0838 is consistent with calculated [M + H]+ of 350.0845. IR (neat, cm−1): 1655 (C=O), 1313 (SO2). Rf (50% EtOAc/hexanes) = 0.46.
2,3-Diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one 1,1-dioxide, 2: Crystals for X-ray were grown by slow evaporation from ethanol solution. 0.079 g (77%). m.p.: 483–484 K (decomposition). 1H NMR (CDCl3): δ(ppm): 8.77 (d, J = 5.1 Hz, 1H), 8.62 (d, J = 8.0 Hz, 1H), 7.67 (dd, J = 8.1, 4.7 Hz, 1H), 7.31 (m, 9H), 5.88 (s, 1H, C2-H). 13C NMR (CDCl3) δ(ppm): 160.5 (C=O), 153.9, 152.2, 141.3, 139.0, 130.2, 129.8, 129.1, 128.7, 128.4, 128.3, 126.4, 82.4 (C2). HRMS (m/z): [M + H]+ of 351.0790 is consistent with calculated [M + H]+ of 351.0797. IR (neat, cm−1): 1655 (C=O), 1325 (SO2). Rf (50% EtOAc/hexanes) = 0.37.
6. Refinement
Crystal data, data collection and structure . The hydrogen atoms were placed in their geometrically calculated positions and refined using the riding model with parent-atom—H lengths of 0.93–0.95 Å (aromatic CH) and 0.98–1.00 Å (methine CH). Isotropic displacement parameters for these atoms were set to 1.2 times Ueq of the parent atom.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S2056989023001524/hb8054sup1.cif
contains datablocks general, 2, 1. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989023001524/hb80541sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989023001524/hb80542sup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001524/hb80541sup4.mol
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001524/hb80542sup5.mol
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001524/hb80541sup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001524/hb80542sup7.cml
Data collection: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022) for (1); SMART V5.634 (Bruker, 2001) for (2). Cell
CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022) for (1); SAINT V6.36A (Bruker, 2001) for (2). Data reduction: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022) for (1); SAINT V6.36A (Bruker, 2016) for (2). Program(s) used to solve structure: olex2.solve 1.3-ac4 (Bourhis et al., 2015) for (1); SHELXS (Sheldrick, 2008) for (2). For both structures, program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3-ac4 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3-ac4 (Dolomanov et al., 2009).C20H15NO3S | F(000) = 1456 |
Mr = 349.39 | Dx = 1.394 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 6.8530 (6) Å | Cell parameters from 6963 reflections |
b = 25.7472 (15) Å | θ = 2.9–70.6° |
c = 19.0240 (12) Å | µ = 1.89 mm−1 |
β = 97.394 (7)° | T = 173 K |
V = 3328.8 (4) Å3 | Block, clear colourless |
Z = 8 | 0.2 × 0.06 × 0.04 mm |
ROD, Synergy Custom system, HyPix-Arc 150 diffractometer | 6557 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 4087 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.074 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 75.7°, θmin = 2.9° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −31→31 |
Tmin = 0.649, Tmax = 1.000 | l = −23→18 |
21581 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.092 | w = 1/[σ2(Fo2) + (0.1722P)2 + 1.2363P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.300 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.66 e Å−3 |
6557 reflections | Δρmin = −1.06 e Å−3 |
452 parameters | Extinction correction: SHELXL2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0038 (5) |
Primary atom site location: iterative |
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 | 0.62556 (19) | 0.74906 (4) | 0.62956 (6) | 0.0454 (4) | |
O1 | 0.4248 (5) | 0.76270 (12) | 0.63479 (18) | 0.0532 (9) | |
O2 | 0.7399 (6) | 0.78342 (13) | 0.59272 (17) | 0.0608 (10) | |
O3 | 0.5497 (5) | 0.61116 (11) | 0.74902 (16) | 0.0456 (8) | |
N1 | 0.6484 (5) | 0.69574 (13) | 0.74977 (18) | 0.0390 (8) | |
C1 | 0.6386 (7) | 0.68627 (17) | 0.5944 (2) | 0.0407 (10) | |
C2 | 0.6537 (7) | 0.6796 (2) | 0.5231 (3) | 0.0501 (12) | |
H2 | 0.654648 | 0.708677 | 0.492500 | 0.060* | |
C3 | 0.6673 (8) | 0.6295 (2) | 0.4972 (3) | 0.0544 (13) | |
H3 | 0.680789 | 0.624314 | 0.448640 | 0.065* | |
C4 | 0.6615 (7) | 0.58719 (19) | 0.5413 (3) | 0.0517 (12) | |
H4 | 0.668259 | 0.553102 | 0.522656 | 0.062* | |
C5 | 0.6457 (7) | 0.59407 (18) | 0.6128 (3) | 0.0489 (12) | |
H5 | 0.643583 | 0.564708 | 0.642941 | 0.059* | |
C6 | 0.6330 (7) | 0.64378 (17) | 0.6404 (2) | 0.0419 (10) | |
C7 | 0.6090 (7) | 0.64872 (16) | 0.7171 (2) | 0.0424 (10) | |
C8 | 0.7557 (7) | 0.73578 (16) | 0.7164 (2) | 0.0428 (10) | |
H8 | 0.887282 | 0.721153 | 0.709704 | 0.051* | |
C9 | 0.7905 (7) | 0.78609 (15) | 0.7569 (2) | 0.0399 (10) | |
C10 | 0.6351 (7) | 0.81491 (17) | 0.7762 (2) | 0.0464 (11) | |
H10 | 0.504192 | 0.802207 | 0.766774 | 0.056* | |
C11 | 0.6728 (9) | 0.86284 (18) | 0.8097 (2) | 0.0537 (13) | |
H11 | 0.566833 | 0.883072 | 0.822377 | 0.064* | |
C12 | 0.8631 (8) | 0.88091 (18) | 0.8244 (3) | 0.0515 (12) | |
H12 | 0.888316 | 0.913247 | 0.847853 | 0.062* | |
C13 | 1.0162 (8) | 0.85202 (19) | 0.8050 (3) | 0.0533 (13) | |
H13 | 1.147062 | 0.864694 | 0.814852 | 0.064* | |
C14 | 0.9815 (8) | 0.80463 (18) | 0.7713 (2) | 0.0490 (12) | |
H14 | 1.088108 | 0.784884 | 0.758093 | 0.059* | |
C15 | 0.6318 (7) | 0.69896 (16) | 0.8253 (2) | 0.0429 (11) | |
C16 | 0.7980 (8) | 0.69680 (18) | 0.8737 (2) | 0.0516 (12) | |
H16 | 0.923333 | 0.691947 | 0.858343 | 0.062* | |
C17 | 0.7812 (10) | 0.7018 (2) | 0.9453 (3) | 0.0638 (16) | |
H17 | 0.895753 | 0.700715 | 0.979190 | 0.077* | |
C18 | 0.6001 (11) | 0.7083 (2) | 0.9673 (3) | 0.0691 (18) | |
H18 | 0.589298 | 0.712069 | 1.016297 | 0.083* | |
C19 | 0.4346 (10) | 0.7092 (2) | 0.9185 (3) | 0.0669 (16) | |
H19 | 0.309207 | 0.713126 | 0.934068 | 0.080* | |
C20 | 0.4482 (8) | 0.70451 (19) | 0.8461 (3) | 0.0537 (12) | |
H20 | 0.333554 | 0.705118 | 0.812218 | 0.064* | |
S2 | 0.13252 (18) | 0.49892 (4) | 0.65164 (6) | 0.0439 (4) | |
O4 | −0.0701 (5) | 0.48580 (12) | 0.65590 (18) | 0.0540 (9) | |
O5 | 0.2516 (6) | 0.46129 (12) | 0.62200 (17) | 0.0565 (10) | |
O6 | 0.0546 (5) | 0.64719 (11) | 0.74688 (16) | 0.0467 (8) | |
N2 | 0.1453 (6) | 0.56260 (13) | 0.76148 (18) | 0.0408 (9) | |
C21 | 0.1453 (7) | 0.55831 (17) | 0.6066 (2) | 0.0413 (10) | |
C22 | 0.1579 (7) | 0.55769 (18) | 0.5345 (2) | 0.0481 (11) | |
H22 | 0.161209 | 0.525749 | 0.509711 | 0.058* | |
C23 | 0.1655 (8) | 0.6047 (2) | 0.4994 (2) | 0.0506 (12) | |
H23 | 0.174775 | 0.605013 | 0.449995 | 0.061* | |
C24 | 0.1596 (7) | 0.65089 (18) | 0.5357 (3) | 0.0506 (12) | |
H24 | 0.164357 | 0.682885 | 0.511127 | 0.061* | |
C25 | 0.1468 (7) | 0.65103 (18) | 0.6081 (2) | 0.0461 (11) | |
H25 | 0.145517 | 0.683064 | 0.632868 | 0.055* | |
C26 | 0.1357 (7) | 0.60427 (17) | 0.6446 (2) | 0.0403 (10) | |
C27 | 0.1111 (7) | 0.60690 (16) | 0.7219 (2) | 0.0420 (10) | |
C28 | 0.2553 (7) | 0.51938 (16) | 0.7368 (2) | 0.0419 (10) | |
H28 | 0.387925 | 0.532827 | 0.729278 | 0.050* | |
C29 | 0.2872 (8) | 0.47302 (16) | 0.7859 (2) | 0.0454 (11) | |
C30 | 0.1322 (9) | 0.44441 (18) | 0.8061 (2) | 0.0556 (14) | |
H30 | 0.000299 | 0.454607 | 0.790836 | 0.067* | |
C31 | 0.1698 (11) | 0.4010 (2) | 0.8486 (3) | 0.0698 (17) | |
H31 | 0.063439 | 0.381662 | 0.862724 | 0.084* | |
C32 | 0.3619 (12) | 0.3856 (2) | 0.8706 (3) | 0.078 (2) | |
H32 | 0.386987 | 0.355338 | 0.898849 | 0.093* | |
C33 | 0.5153 (11) | 0.4141 (2) | 0.8514 (3) | 0.0766 (19) | |
H33 | 0.646738 | 0.404008 | 0.867541 | 0.092* | |
C34 | 0.4806 (9) | 0.4575 (2) | 0.8087 (3) | 0.0590 (14) | |
H34 | 0.587839 | 0.476665 | 0.794842 | 0.071* | |
C35 | 0.1235 (7) | 0.56603 (16) | 0.8364 (2) | 0.0434 (11) | |
C36 | −0.0597 (8) | 0.5610 (2) | 0.8570 (3) | 0.0567 (13) | |
H36 | −0.172083 | 0.556851 | 0.822632 | 0.068* | |
C37 | −0.0791 (10) | 0.5620 (2) | 0.9288 (3) | 0.0699 (16) | |
H37 | −0.205174 | 0.558456 | 0.944078 | 0.084* | |
C38 | 0.0863 (11) | 0.5680 (3) | 0.9778 (3) | 0.0791 (19) | |
H38 | 0.073055 | 0.568055 | 1.026936 | 0.095* | |
C39 | 0.2698 (11) | 0.5741 (3) | 0.9570 (3) | 0.0789 (19) | |
H39 | 0.381975 | 0.578891 | 0.991238 | 0.095* | |
C40 | 0.2890 (9) | 0.5731 (2) | 0.8853 (2) | 0.0570 (13) | |
H40 | 0.414579 | 0.577332 | 0.869928 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0655 (9) | 0.0296 (6) | 0.0391 (6) | −0.0001 (5) | −0.0002 (5) | 0.0001 (4) |
O1 | 0.061 (2) | 0.0395 (17) | 0.057 (2) | 0.0105 (16) | −0.0017 (16) | −0.0030 (15) |
O2 | 0.097 (3) | 0.0413 (19) | 0.0443 (18) | −0.0202 (18) | 0.0095 (18) | 0.0079 (15) |
O3 | 0.058 (2) | 0.0301 (15) | 0.0467 (17) | −0.0032 (14) | 0.0004 (14) | −0.0002 (13) |
N1 | 0.053 (2) | 0.0259 (17) | 0.0377 (19) | −0.0017 (15) | 0.0038 (16) | −0.0035 (14) |
C1 | 0.050 (3) | 0.033 (2) | 0.039 (2) | 0.0015 (19) | 0.0021 (18) | −0.0064 (18) |
C2 | 0.057 (3) | 0.048 (3) | 0.042 (3) | −0.005 (2) | −0.003 (2) | 0.000 (2) |
C3 | 0.059 (3) | 0.057 (3) | 0.046 (3) | 0.000 (3) | 0.001 (2) | −0.013 (2) |
C4 | 0.060 (3) | 0.044 (3) | 0.050 (3) | 0.000 (2) | 0.002 (2) | −0.021 (2) |
C5 | 0.056 (3) | 0.035 (2) | 0.053 (3) | 0.003 (2) | −0.004 (2) | −0.008 (2) |
C6 | 0.055 (3) | 0.032 (2) | 0.038 (2) | 0.0004 (19) | 0.0021 (19) | −0.0066 (18) |
C7 | 0.054 (3) | 0.024 (2) | 0.048 (3) | 0.0027 (19) | 0.002 (2) | −0.0033 (18) |
C8 | 0.060 (3) | 0.025 (2) | 0.043 (2) | −0.0033 (19) | 0.007 (2) | −0.0053 (18) |
C9 | 0.056 (3) | 0.0244 (19) | 0.039 (2) | 0.0002 (18) | 0.0016 (19) | −0.0020 (17) |
C10 | 0.059 (3) | 0.032 (2) | 0.046 (3) | 0.001 (2) | −0.003 (2) | −0.003 (2) |
C11 | 0.080 (4) | 0.035 (2) | 0.044 (3) | 0.005 (2) | 0.000 (2) | −0.001 (2) |
C12 | 0.075 (4) | 0.030 (2) | 0.048 (3) | −0.010 (2) | 0.001 (2) | −0.005 (2) |
C13 | 0.061 (3) | 0.042 (3) | 0.055 (3) | −0.013 (2) | 0.001 (2) | −0.004 (2) |
C14 | 0.061 (3) | 0.038 (2) | 0.047 (3) | −0.007 (2) | 0.002 (2) | −0.001 (2) |
C15 | 0.062 (3) | 0.027 (2) | 0.039 (2) | −0.003 (2) | 0.006 (2) | −0.0033 (18) |
C16 | 0.069 (3) | 0.043 (3) | 0.039 (2) | −0.005 (2) | −0.007 (2) | 0.005 (2) |
C17 | 0.102 (5) | 0.047 (3) | 0.038 (3) | −0.004 (3) | −0.006 (3) | 0.001 (2) |
C18 | 0.128 (6) | 0.038 (3) | 0.043 (3) | −0.012 (3) | 0.020 (3) | −0.003 (2) |
C19 | 0.097 (5) | 0.047 (3) | 0.063 (3) | −0.009 (3) | 0.033 (3) | −0.014 (3) |
C20 | 0.067 (3) | 0.042 (3) | 0.055 (3) | 0.000 (2) | 0.017 (2) | −0.009 (2) |
S2 | 0.0639 (8) | 0.0257 (5) | 0.0396 (6) | 0.0007 (5) | −0.0026 (5) | −0.0015 (4) |
O4 | 0.063 (2) | 0.0390 (17) | 0.057 (2) | −0.0106 (16) | −0.0041 (16) | 0.0020 (15) |
O5 | 0.087 (3) | 0.0370 (17) | 0.0442 (18) | 0.0210 (17) | 0.0040 (17) | −0.0065 (14) |
O6 | 0.060 (2) | 0.0281 (15) | 0.0503 (18) | 0.0065 (14) | 0.0026 (15) | −0.0040 (14) |
N2 | 0.056 (2) | 0.0279 (17) | 0.0372 (19) | −0.0005 (16) | 0.0035 (16) | 0.0005 (15) |
C21 | 0.051 (3) | 0.031 (2) | 0.039 (2) | 0.0002 (19) | −0.0025 (19) | 0.0034 (18) |
C22 | 0.059 (3) | 0.041 (2) | 0.043 (2) | 0.006 (2) | 0.001 (2) | −0.006 (2) |
C23 | 0.061 (3) | 0.052 (3) | 0.038 (2) | 0.005 (2) | 0.004 (2) | 0.008 (2) |
C24 | 0.058 (3) | 0.037 (2) | 0.056 (3) | 0.001 (2) | 0.004 (2) | 0.016 (2) |
C25 | 0.053 (3) | 0.034 (2) | 0.050 (3) | 0.000 (2) | 0.000 (2) | 0.004 (2) |
C26 | 0.050 (3) | 0.032 (2) | 0.038 (2) | 0.0057 (18) | −0.0014 (18) | 0.0016 (18) |
C27 | 0.052 (3) | 0.029 (2) | 0.043 (2) | −0.0015 (19) | −0.0007 (19) | 0.0006 (19) |
C28 | 0.060 (3) | 0.030 (2) | 0.035 (2) | 0.001 (2) | 0.0034 (19) | −0.0011 (18) |
C29 | 0.071 (3) | 0.028 (2) | 0.035 (2) | 0.003 (2) | −0.002 (2) | −0.0009 (18) |
C30 | 0.091 (4) | 0.035 (2) | 0.041 (3) | −0.004 (2) | 0.007 (2) | 0.002 (2) |
C31 | 0.125 (6) | 0.038 (3) | 0.046 (3) | −0.002 (3) | 0.012 (3) | 0.003 (2) |
C32 | 0.142 (7) | 0.042 (3) | 0.045 (3) | 0.018 (4) | −0.004 (4) | 0.009 (2) |
C33 | 0.109 (5) | 0.057 (3) | 0.057 (3) | 0.023 (4) | −0.018 (3) | 0.004 (3) |
C34 | 0.079 (4) | 0.043 (3) | 0.049 (3) | 0.011 (3) | −0.013 (3) | 0.000 (2) |
C35 | 0.062 (3) | 0.030 (2) | 0.039 (2) | 0.003 (2) | 0.008 (2) | 0.0006 (18) |
C36 | 0.064 (3) | 0.053 (3) | 0.054 (3) | 0.003 (3) | 0.011 (2) | 0.009 (2) |
C37 | 0.087 (5) | 0.069 (4) | 0.057 (3) | 0.013 (3) | 0.022 (3) | 0.008 (3) |
C38 | 0.114 (6) | 0.076 (4) | 0.050 (3) | 0.006 (4) | 0.021 (4) | −0.005 (3) |
C39 | 0.106 (5) | 0.088 (5) | 0.040 (3) | −0.006 (4) | −0.003 (3) | −0.007 (3) |
C40 | 0.074 (4) | 0.055 (3) | 0.039 (3) | −0.005 (3) | −0.004 (2) | −0.005 (2) |
S1—O1 | 1.436 (4) | S2—O4 | 1.442 (4) |
S1—O2 | 1.425 (3) | S2—O5 | 1.429 (3) |
S1—C1 | 1.756 (4) | S2—C21 | 1.760 (4) |
S1—C8 | 1.806 (5) | S2—C28 | 1.805 (4) |
O3—C7 | 1.239 (5) | O6—C27 | 1.224 (5) |
N1—C7 | 1.372 (5) | N2—C27 | 1.370 (5) |
N1—C8 | 1.459 (5) | N2—C28 | 1.455 (5) |
N1—C15 | 1.458 (5) | N2—C35 | 1.454 (5) |
C1—C2 | 1.383 (6) | C21—C22 | 1.385 (6) |
C1—C6 | 1.405 (6) | C21—C26 | 1.393 (6) |
C2—H2 | 0.9500 | C22—H22 | 0.9500 |
C2—C3 | 1.387 (7) | C22—C23 | 1.386 (6) |
C3—H3 | 0.9500 | C23—H23 | 0.9500 |
C3—C4 | 1.378 (7) | C23—C24 | 1.380 (7) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C4—C5 | 1.390 (6) | C24—C25 | 1.392 (6) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C5—C6 | 1.390 (6) | C25—C26 | 1.397 (6) |
C6—C7 | 1.494 (6) | C26—C27 | 1.502 (6) |
C8—H8 | 1.0000 | C28—H28 | 1.0000 |
C8—C9 | 1.510 (5) | C28—C29 | 1.514 (6) |
C9—C10 | 1.386 (6) | C29—C30 | 1.387 (7) |
C9—C14 | 1.387 (7) | C29—C34 | 1.399 (7) |
C10—H10 | 0.9500 | C30—H30 | 0.9500 |
C10—C11 | 1.398 (6) | C30—C31 | 1.383 (7) |
C11—H11 | 0.9500 | C31—H31 | 0.9500 |
C11—C12 | 1.379 (7) | C31—C32 | 1.387 (9) |
C12—H12 | 0.9500 | C32—H32 | 0.9500 |
C12—C13 | 1.375 (7) | C32—C33 | 1.370 (9) |
C13—H13 | 0.9500 | C33—H33 | 0.9500 |
C13—C14 | 1.385 (6) | C33—C34 | 1.383 (7) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.370 (6) | C35—C36 | 1.369 (7) |
C15—C20 | 1.375 (7) | C35—C40 | 1.383 (6) |
C16—H16 | 0.9500 | C36—H36 | 0.9500 |
C16—C17 | 1.388 (7) | C36—C37 | 1.391 (7) |
C17—H17 | 0.9500 | C37—H37 | 0.9500 |
C17—C18 | 1.370 (9) | C37—C38 | 1.381 (9) |
C18—H18 | 0.9500 | C38—H38 | 0.9500 |
C18—C19 | 1.370 (9) | C38—C39 | 1.375 (9) |
C19—H19 | 0.9500 | C39—H39 | 0.9500 |
C19—C20 | 1.397 (7) | C39—C40 | 1.387 (7) |
C20—H20 | 0.9500 | C40—H40 | 0.9500 |
O1—S1—C1 | 110.4 (2) | O4—S2—C21 | 109.8 (2) |
O1—S1—C8 | 110.4 (2) | O4—S2—C28 | 111.0 (2) |
O2—S1—O1 | 118.4 (2) | O5—S2—O4 | 117.8 (2) |
O2—S1—C1 | 109.0 (2) | O5—S2—C21 | 109.3 (2) |
O2—S1—C8 | 109.2 (2) | O5—S2—C28 | 109.2 (2) |
C1—S1—C8 | 97.5 (2) | C21—S2—C28 | 97.9 (2) |
C7—N1—C8 | 120.4 (4) | C27—N2—C28 | 121.2 (4) |
C7—N1—C15 | 117.5 (4) | C27—N2—C35 | 117.1 (4) |
C15—N1—C8 | 119.8 (3) | C35—N2—C28 | 119.0 (3) |
C2—C1—S1 | 120.2 (4) | C22—C21—S2 | 119.0 (3) |
C2—C1—C6 | 121.6 (4) | C22—C21—C26 | 122.5 (4) |
C6—C1—S1 | 118.2 (3) | C26—C21—S2 | 118.5 (3) |
C1—C2—H2 | 120.6 | C21—C22—H22 | 120.7 |
C1—C2—C3 | 118.7 (5) | C21—C22—C23 | 118.6 (4) |
C3—C2—H2 | 120.6 | C23—C22—H22 | 120.7 |
C2—C3—H3 | 119.7 | C22—C23—H23 | 119.8 |
C4—C3—C2 | 120.6 (4) | C24—C23—C22 | 120.4 (4) |
C4—C3—H3 | 119.7 | C24—C23—H23 | 119.8 |
C3—C4—H4 | 119.8 | C23—C24—H24 | 119.7 |
C3—C4—C5 | 120.5 (4) | C23—C24—C25 | 120.5 (4) |
C5—C4—H4 | 119.8 | C25—C24—H24 | 119.7 |
C4—C5—H5 | 119.9 | C24—C25—H25 | 119.9 |
C4—C5—C6 | 120.2 (5) | C24—C25—C26 | 120.3 (4) |
C6—C5—H5 | 119.9 | C26—C25—H25 | 119.9 |
C1—C6—C7 | 123.9 (4) | C21—C26—C25 | 117.7 (4) |
C5—C6—C1 | 118.3 (4) | C21—C26—C27 | 124.4 (4) |
C5—C6—C7 | 117.8 (4) | C25—C26—C27 | 117.9 (4) |
O3—C7—N1 | 121.6 (4) | O6—C27—N2 | 122.1 (4) |
O3—C7—C6 | 119.8 (4) | O6—C27—C26 | 119.9 (4) |
N1—C7—C6 | 118.6 (4) | N2—C27—C26 | 117.9 (4) |
S1—C8—H8 | 107.6 | S2—C28—H28 | 107.4 |
N1—C8—S1 | 108.3 (3) | N2—C28—S2 | 108.2 (3) |
N1—C8—H8 | 107.6 | N2—C28—H28 | 107.4 |
N1—C8—C9 | 116.0 (4) | N2—C28—C29 | 116.3 (4) |
C9—C8—S1 | 109.3 (3) | C29—C28—S2 | 109.7 (3) |
C9—C8—H8 | 107.6 | C29—C28—H28 | 107.4 |
C10—C9—C8 | 121.2 (4) | C30—C29—C28 | 122.3 (5) |
C10—C9—C14 | 120.1 (4) | C30—C29—C34 | 119.4 (5) |
C14—C9—C8 | 118.6 (4) | C34—C29—C28 | 118.2 (5) |
C9—C10—H10 | 120.3 | C29—C30—H30 | 120.0 |
C9—C10—C11 | 119.4 (5) | C31—C30—C29 | 119.9 (6) |
C11—C10—H10 | 120.3 | C31—C30—H30 | 120.0 |
C10—C11—H11 | 119.8 | C30—C31—H31 | 119.8 |
C12—C11—C10 | 120.3 (5) | C30—C31—C32 | 120.4 (6) |
C12—C11—H11 | 119.8 | C32—C31—H31 | 119.8 |
C11—C12—H12 | 120.1 | C31—C32—H32 | 120.1 |
C13—C12—C11 | 119.8 (5) | C33—C32—C31 | 119.8 (5) |
C13—C12—H12 | 120.1 | C33—C32—H32 | 120.1 |
C12—C13—H13 | 119.7 | C32—C33—H33 | 119.7 |
C12—C13—C14 | 120.6 (5) | C32—C33—C34 | 120.6 (6) |
C14—C13—H13 | 119.7 | C34—C33—H33 | 119.7 |
C9—C14—H14 | 120.1 | C29—C34—H34 | 120.1 |
C13—C14—C9 | 119.7 (5) | C33—C34—C29 | 119.8 (6) |
C13—C14—H14 | 120.1 | C33—C34—H34 | 120.1 |
C16—C15—N1 | 119.7 (4) | C36—C35—N2 | 119.2 (4) |
C16—C15—C20 | 121.6 (5) | C36—C35—C40 | 121.5 (5) |
C20—C15—N1 | 118.7 (4) | C40—C35—N2 | 119.3 (4) |
C15—C16—H16 | 120.4 | C35—C36—H36 | 120.4 |
C15—C16—C17 | 119.3 (5) | C35—C36—C37 | 119.2 (5) |
C17—C16—H16 | 120.4 | C37—C36—H36 | 120.4 |
C16—C17—H17 | 119.9 | C36—C37—H37 | 120.3 |
C18—C17—C16 | 120.3 (5) | C38—C37—C36 | 119.4 (6) |
C18—C17—H17 | 119.9 | C38—C37—H37 | 120.3 |
C17—C18—H18 | 120.0 | C37—C38—H38 | 119.3 |
C17—C18—C19 | 119.9 (5) | C39—C38—C37 | 121.3 (6) |
C19—C18—H18 | 120.0 | C39—C38—H38 | 119.3 |
C18—C19—H19 | 119.6 | C38—C39—H39 | 120.4 |
C18—C19—C20 | 120.8 (6) | C38—C39—C40 | 119.2 (6) |
C20—C19—H19 | 119.6 | C40—C39—H39 | 120.4 |
C15—C20—C19 | 118.2 (5) | C35—C40—C39 | 119.4 (6) |
C15—C20—H20 | 120.9 | C35—C40—H40 | 120.3 |
C19—C20—H20 | 120.9 | C39—C40—H40 | 120.3 |
S1—C1—C2—C3 | 178.8 (4) | S2—C21—C22—C23 | 179.2 (4) |
S1—C1—C6—C5 | −179.3 (4) | S2—C21—C26—C25 | 179.8 (3) |
S1—C1—C6—C7 | 2.4 (6) | S2—C21—C26—C27 | −1.2 (7) |
S1—C8—C9—C10 | 65.3 (5) | S2—C28—C29—C30 | −62.1 (5) |
S1—C8—C9—C14 | −111.2 (4) | S2—C28—C29—C34 | 114.8 (4) |
O1—S1—C1—C2 | 98.3 (4) | O4—S2—C21—C22 | −95.0 (4) |
O1—S1—C1—C6 | −81.6 (4) | O4—S2—C21—C26 | 82.9 (4) |
O1—S1—C8—N1 | 55.2 (3) | O4—S2—C28—N2 | −56.2 (3) |
O1—S1—C8—C9 | −72.2 (4) | O4—S2—C28—C29 | 71.6 (4) |
O2—S1—C1—C2 | −33.3 (5) | O5—S2—C21—C22 | 35.7 (4) |
O2—S1—C1—C6 | 146.8 (4) | O5—S2—C21—C26 | −146.4 (4) |
O2—S1—C8—N1 | −173.1 (3) | O5—S2—C28—N2 | 172.3 (3) |
O2—S1—C8—C9 | 59.6 (4) | O5—S2—C28—C29 | −59.9 (4) |
N1—C8—C9—C10 | −57.5 (6) | N2—C28—C29—C30 | 61.0 (6) |
N1—C8—C9—C14 | 125.9 (5) | N2—C28—C29—C34 | −122.0 (5) |
N1—C15—C16—C17 | 177.7 (4) | N2—C35—C36—C37 | 177.2 (5) |
N1—C15—C20—C19 | −178.0 (4) | N2—C35—C40—C39 | −177.1 (5) |
C1—S1—C8—N1 | −59.9 (3) | C21—S2—C28—N2 | 58.7 (3) |
C1—S1—C8—C9 | 172.8 (3) | C21—S2—C28—C29 | −173.5 (4) |
C1—C2—C3—C4 | 1.5 (8) | C21—C22—C23—C24 | −0.3 (8) |
C1—C6—C7—O3 | 159.3 (4) | C21—C26—C27—O6 | −161.4 (4) |
C1—C6—C7—N1 | −18.8 (7) | C21—C26—C27—N2 | 15.7 (7) |
C2—C1—C6—C5 | 0.8 (7) | C22—C21—C26—C25 | −2.4 (7) |
C2—C1—C6—C7 | −177.5 (4) | C22—C21—C26—C27 | 176.6 (4) |
C2—C3—C4—C5 | −1.3 (8) | C22—C23—C24—C25 | 0.3 (8) |
C3—C4—C5—C6 | 0.9 (8) | C23—C24—C25—C26 | −1.3 (7) |
C4—C5—C6—C1 | −0.6 (7) | C24—C25—C26—C21 | 2.3 (7) |
C4—C5—C6—C7 | 177.8 (4) | C24—C25—C26—C27 | −176.8 (4) |
C5—C6—C7—O3 | −19.0 (7) | C25—C26—C27—O6 | 17.6 (7) |
C5—C6—C7—N1 | 162.8 (4) | C25—C26—C27—N2 | −165.3 (4) |
C6—C1—C2—C3 | −1.3 (7) | C26—C21—C22—C23 | 1.4 (8) |
C7—N1—C8—S1 | 56.4 (5) | C27—N2—C28—S2 | −57.3 (5) |
C7—N1—C8—C9 | 179.8 (4) | C27—N2—C28—C29 | 178.8 (4) |
C7—N1—C15—C16 | 100.3 (5) | C27—N2—C35—C36 | 83.8 (5) |
C7—N1—C15—C20 | −80.1 (5) | C27—N2—C35—C40 | −97.7 (5) |
C8—S1—C1—C2 | −146.7 (4) | C28—S2—C21—C22 | 149.2 (4) |
C8—S1—C1—C6 | 33.4 (4) | C28—S2—C21—C26 | −32.9 (4) |
C8—N1—C7—O3 | 167.2 (4) | C28—N2—C27—O6 | −165.2 (4) |
C8—N1—C7—C6 | −14.7 (6) | C28—N2—C27—C26 | 17.7 (6) |
C8—N1—C15—C16 | −62.6 (5) | C28—N2—C35—C36 | −114.4 (5) |
C8—N1—C15—C20 | 117.0 (5) | C28—N2—C35—C40 | 64.1 (6) |
C8—C9—C10—C11 | −176.0 (4) | C28—C29—C30—C31 | 177.1 (4) |
C8—C9—C14—C13 | 176.6 (4) | C28—C29—C34—C33 | −177.5 (5) |
C9—C10—C11—C12 | −1.0 (7) | C29—C30—C31—C32 | −0.6 (8) |
C10—C9—C14—C13 | 0.0 (7) | C30—C29—C34—C33 | −0.5 (7) |
C10—C11—C12—C13 | 1.0 (7) | C30—C31—C32—C33 | 1.4 (9) |
C11—C12—C13—C14 | −0.5 (7) | C31—C32—C33—C34 | −1.7 (9) |
C12—C13—C14—C9 | 0.0 (7) | C32—C33—C34—C29 | 1.2 (8) |
C14—C9—C10—C11 | 0.5 (7) | C34—C29—C30—C31 | 0.2 (7) |
C15—N1—C7—O3 | 4.4 (7) | C35—N2—C27—O6 | −3.8 (7) |
C15—N1—C7—C6 | −177.5 (4) | C35—N2—C27—C26 | 179.1 (4) |
C15—N1—C8—S1 | −141.2 (3) | C35—N2—C28—S2 | 141.6 (3) |
C15—N1—C8—C9 | −17.8 (6) | C35—N2—C28—C29 | 17.7 (6) |
C15—C16—C17—C18 | 0.7 (8) | C35—C36—C37—C38 | 0.1 (8) |
C16—C15—C20—C19 | 1.5 (7) | C36—C35—C40—C39 | 1.4 (8) |
C16—C17—C18—C19 | 0.7 (8) | C36—C37—C38—C39 | 1.2 (10) |
C17—C18—C19—C20 | −1.0 (8) | C37—C38—C39—C40 | −1.1 (10) |
C18—C19—C20—C15 | −0.1 (7) | C38—C39—C40—C35 | −0.1 (9) |
C20—C15—C16—C17 | −1.8 (7) | C40—C35—C36—C37 | −1.3 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.95 | 2.65 | 3.353 (6) | 131 |
C8—H8···O6ii | 1.00 | 2.29 | 3.070 (6) | 134 |
C16—H16···O6ii | 0.95 | 2.67 | 3.410 (6) | 135 |
C20—H20···O6 | 0.95 | 2.61 | 3.422 (6) | 144 |
C28—H28···O3 | 1.00 | 2.31 | 3.096 (5) | 135 |
C36—H36···O3iii | 0.95 | 2.62 | 3.412 (6) | 141 |
C40—H40···O3 | 0.95 | 2.73 | 3.473 (7) | 136 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z. |
C19H14N2O3S | F(000) = 1456 |
Mr = 350.38 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8584 (19) Å | Cell parameters from 5480 reflections |
b = 25.487 (7) Å | θ = 2.3–26.1° |
c = 19.008 (5) Å | µ = 0.22 mm−1 |
β = 94.669 (7)° | T = 298 K |
V = 3311.6 (16) Å3 | Needle, colorless |
Z = 8 | 0.22 × 0.04 × 0.02 mm |
Bruker CCD area detector diffractometer | 5509 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.040 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 28.4°, θmin = 1.3° |
Tmin = 0.237, Tmax = 0.9 | h = −9→9 |
29524 measured reflections | k = −32→32 |
7909 independent reflections | l = −23→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.239P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
7909 reflections | Δρmax = 0.31 e Å−3 |
451 parameters | Δρmin = −0.26 e Å−3 |
0 restraints |
Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm. |
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 | 0.63430 (8) | 0.74816 (2) | 0.62562 (3) | 0.04230 (15) | |
O1 | 0.4325 (2) | 0.75929 (6) | 0.63311 (8) | 0.0578 (4) | |
O2 | 0.7474 (3) | 0.78399 (6) | 0.58785 (8) | 0.0681 (5) | |
O3 | 0.5672 (2) | 0.60846 (5) | 0.74613 (7) | 0.0460 (3) | |
N1 | 0.6591 (2) | 0.69392 (5) | 0.74620 (8) | 0.0339 (3) | |
C1 | 0.6539 (3) | 0.68391 (7) | 0.59048 (10) | 0.0372 (4) | |
N2 | 0.6667 (3) | 0.68078 (7) | 0.52113 (9) | 0.0485 (4) | |
C3 | 0.6840 (3) | 0.63236 (9) | 0.49538 (11) | 0.0536 (6) | |
H3 | 0.693463 | 0.628667 | 0.447104 | 0.064* | |
C4 | 0.6885 (3) | 0.58773 (8) | 0.53596 (11) | 0.0484 (5) | |
H4 | 0.702610 | 0.554955 | 0.515465 | 0.058* | |
C5 | 0.6718 (3) | 0.59221 (7) | 0.60787 (11) | 0.0409 (5) | |
H5 | 0.672293 | 0.562470 | 0.636234 | 0.049* | |
C6 | 0.6543 (3) | 0.64206 (7) | 0.63705 (10) | 0.0342 (4) | |
C7 | 0.6251 (3) | 0.64642 (7) | 0.71450 (10) | 0.0348 (4) | |
C8 | 0.7641 (3) | 0.73481 (6) | 0.71038 (9) | 0.0329 (4) | |
H8 | 0.892706 | 0.720657 | 0.701537 | 0.039* | |
C9 | 0.7973 (3) | 0.78510 (6) | 0.75095 (9) | 0.0349 (4) | |
C10 | 0.6433 (3) | 0.81482 (7) | 0.77271 (11) | 0.0434 (5) | |
H10 | 0.515080 | 0.803440 | 0.763175 | 0.052* | |
C11 | 0.6813 (4) | 0.86115 (8) | 0.80844 (11) | 0.0521 (6) | |
H11 | 0.578441 | 0.880859 | 0.823488 | 0.062* | |
C12 | 0.8701 (4) | 0.87842 (8) | 0.82198 (12) | 0.0566 (6) | |
H12 | 0.894905 | 0.909751 | 0.846138 | 0.068* | |
C13 | 1.0224 (4) | 0.84948 (9) | 0.79988 (12) | 0.0586 (6) | |
H13 | 1.150197 | 0.861340 | 0.808938 | 0.070* | |
C14 | 0.9866 (3) | 0.80271 (8) | 0.76418 (11) | 0.0465 (5) | |
H14 | 1.090055 | 0.783227 | 0.749150 | 0.056* | |
C15 | 0.6365 (3) | 0.69882 (7) | 0.82159 (10) | 0.0386 (4) | |
C16 | 0.7981 (4) | 0.69689 (8) | 0.86865 (11) | 0.0536 (6) | |
H16 | 0.920527 | 0.689583 | 0.853283 | 0.064* | |
C17 | 0.7772 (5) | 0.70596 (10) | 0.93957 (13) | 0.0721 (7) | |
H17 | 0.886765 | 0.705311 | 0.971784 | 0.087* | |
C18 | 0.5986 (5) | 0.71578 (10) | 0.96239 (14) | 0.0763 (9) | |
H18 | 0.586778 | 0.722023 | 1.010056 | 0.092* | |
C19 | 0.4354 (5) | 0.71657 (10) | 0.91580 (16) | 0.0763 (8) | |
H19 | 0.313012 | 0.722843 | 0.931876 | 0.092* | |
C20 | 0.4533 (3) | 0.70791 (9) | 0.84404 (13) | 0.0576 (6) | |
H20 | 0.343538 | 0.708267 | 0.811932 | 0.069* | |
S2 | 0.13994 (8) | 0.49436 (2) | 0.65360 (2) | 0.03987 (15) | |
O4 | −0.0638 (2) | 0.48498 (5) | 0.66084 (8) | 0.0538 (4) | |
O5 | 0.2549 (3) | 0.45389 (5) | 0.62563 (8) | 0.0642 (5) | |
O6 | 0.0749 (2) | 0.64799 (5) | 0.73881 (7) | 0.0468 (4) | |
N3 | 0.1540 (2) | 0.56289 (5) | 0.75909 (8) | 0.0356 (4) | |
C21 | 0.1620 (3) | 0.55275 (6) | 0.60387 (10) | 0.0348 (4) | |
N4 | 0.1748 (2) | 0.54607 (6) | 0.53518 (8) | 0.0432 (4) | |
C23 | 0.1843 (3) | 0.58965 (8) | 0.49718 (11) | 0.0485 (5) | |
H23 | 0.191493 | 0.586542 | 0.448712 | 0.058* | |
C24 | 0.1841 (3) | 0.63940 (8) | 0.52628 (11) | 0.0469 (5) | |
H24 | 0.192899 | 0.668864 | 0.497855 | 0.056* | |
C25 | 0.1706 (3) | 0.64482 (7) | 0.59793 (11) | 0.0410 (5) | |
H25 | 0.169557 | 0.677987 | 0.618283 | 0.049* | |
C26 | 0.1587 (2) | 0.60021 (6) | 0.63938 (9) | 0.0327 (4) | |
C27 | 0.1291 (3) | 0.60600 (7) | 0.71683 (10) | 0.0354 (4) | |
C28 | 0.2623 (3) | 0.51705 (6) | 0.73556 (9) | 0.0340 (4) | |
H28 | 0.392932 | 0.529097 | 0.725573 | 0.041* | |
C29 | 0.2885 (3) | 0.47234 (7) | 0.78757 (10) | 0.0416 (5) | |
C30 | 0.1352 (4) | 0.44247 (8) | 0.80797 (11) | 0.0533 (6) | |
H30 | 0.007471 | 0.450892 | 0.791761 | 0.064* | |
C31 | 0.1710 (5) | 0.40003 (9) | 0.85245 (13) | 0.0733 (8) | |
H31 | 0.067265 | 0.379812 | 0.865727 | 0.088* | |
C32 | 0.3580 (6) | 0.38766 (11) | 0.87699 (14) | 0.0930 (11) | |
H32 | 0.381106 | 0.359142 | 0.907028 | 0.112* | |
C33 | 0.5112 (5) | 0.41710 (12) | 0.85749 (15) | 0.0914 (10) | |
H33 | 0.638235 | 0.408655 | 0.874614 | 0.110* | |
C34 | 0.4785 (4) | 0.45936 (9) | 0.81249 (13) | 0.0633 (6) | |
H34 | 0.583346 | 0.479040 | 0.798928 | 0.076* | |
C35 | 0.1232 (3) | 0.56794 (7) | 0.83321 (10) | 0.0422 (5) | |
C36 | −0.0608 (4) | 0.55993 (9) | 0.85463 (13) | 0.0618 (6) | |
H36 | −0.165756 | 0.553010 | 0.821831 | 0.074* | |
C37 | −0.0874 (5) | 0.56238 (12) | 0.92666 (17) | 0.0913 (10) | |
H37 | −0.210699 | 0.556903 | 0.942374 | 0.110* | |
C38 | 0.0697 (7) | 0.57292 (14) | 0.97419 (16) | 0.1078 (12) | |
H38 | 0.052867 | 0.573858 | 1.022227 | 0.129* | |
C39 | 0.2486 (6) | 0.58194 (15) | 0.95149 (15) | 0.1071 (12) | |
H39 | 0.353065 | 0.589783 | 0.984069 | 0.129* | |
C40 | 0.2778 (4) | 0.57965 (10) | 0.88050 (12) | 0.0692 (7) | |
H40 | 0.400987 | 0.585986 | 0.865134 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0610 (4) | 0.0304 (2) | 0.0346 (3) | 0.0002 (2) | −0.0017 (2) | −0.00136 (19) |
O1 | 0.0600 (10) | 0.0494 (8) | 0.0608 (10) | 0.0194 (7) | −0.0144 (8) | −0.0116 (7) |
O2 | 0.1144 (14) | 0.0454 (9) | 0.0452 (9) | −0.0225 (9) | 0.0100 (9) | 0.0039 (7) |
O3 | 0.0600 (9) | 0.0318 (7) | 0.0461 (8) | −0.0101 (6) | 0.0053 (7) | −0.0014 (6) |
N1 | 0.0438 (9) | 0.0268 (7) | 0.0309 (8) | −0.0005 (6) | 0.0024 (7) | −0.0046 (6) |
C1 | 0.0402 (11) | 0.0361 (9) | 0.0349 (10) | 0.0008 (8) | 0.0009 (8) | −0.0062 (8) |
N2 | 0.0591 (11) | 0.0516 (10) | 0.0347 (9) | −0.0033 (8) | 0.0032 (8) | −0.0088 (8) |
C3 | 0.0576 (14) | 0.0645 (14) | 0.0385 (12) | −0.0032 (11) | 0.0019 (10) | −0.0208 (11) |
C4 | 0.0447 (12) | 0.0473 (11) | 0.0531 (13) | −0.0001 (9) | 0.0036 (10) | −0.0232 (10) |
C5 | 0.0395 (11) | 0.0353 (10) | 0.0473 (12) | 0.0008 (8) | −0.0003 (9) | −0.0110 (8) |
C6 | 0.0326 (10) | 0.0308 (9) | 0.0389 (10) | −0.0009 (7) | 0.0012 (8) | −0.0095 (7) |
C7 | 0.0355 (10) | 0.0298 (9) | 0.0385 (10) | 0.0002 (7) | −0.0008 (8) | −0.0051 (8) |
C8 | 0.0362 (10) | 0.0277 (8) | 0.0344 (10) | 0.0000 (7) | 0.0011 (8) | −0.0026 (7) |
C9 | 0.0458 (11) | 0.0249 (8) | 0.0334 (10) | −0.0018 (7) | 0.0002 (8) | −0.0012 (7) |
C10 | 0.0490 (12) | 0.0327 (9) | 0.0477 (12) | 0.0019 (8) | −0.0012 (9) | −0.0064 (8) |
C11 | 0.0706 (16) | 0.0340 (10) | 0.0513 (13) | 0.0069 (10) | 0.0034 (11) | −0.0091 (9) |
C12 | 0.0846 (18) | 0.0377 (11) | 0.0478 (13) | −0.0140 (11) | 0.0078 (12) | −0.0137 (10) |
C13 | 0.0616 (15) | 0.0550 (13) | 0.0587 (15) | −0.0228 (11) | 0.0017 (12) | −0.0157 (11) |
C14 | 0.0502 (13) | 0.0427 (11) | 0.0466 (12) | −0.0043 (9) | 0.0038 (10) | −0.0091 (9) |
C15 | 0.0544 (12) | 0.0278 (9) | 0.0342 (10) | −0.0031 (8) | 0.0074 (9) | −0.0057 (7) |
C16 | 0.0689 (15) | 0.0515 (12) | 0.0396 (12) | 0.0056 (11) | −0.0005 (11) | −0.0025 (10) |
C17 | 0.110 (2) | 0.0658 (16) | 0.0388 (13) | 0.0026 (15) | −0.0039 (14) | −0.0051 (12) |
C18 | 0.135 (3) | 0.0554 (15) | 0.0415 (14) | −0.0112 (16) | 0.0260 (17) | −0.0101 (11) |
C19 | 0.098 (2) | 0.0676 (17) | 0.0699 (19) | −0.0138 (15) | 0.0470 (17) | −0.0170 (14) |
C20 | 0.0604 (15) | 0.0546 (13) | 0.0598 (15) | −0.0074 (11) | 0.0178 (12) | −0.0099 (11) |
S2 | 0.0619 (3) | 0.0239 (2) | 0.0325 (3) | 0.0015 (2) | −0.0038 (2) | −0.00153 (18) |
O4 | 0.0589 (10) | 0.0428 (8) | 0.0571 (9) | −0.0192 (7) | −0.0116 (7) | 0.0086 (7) |
O5 | 0.1104 (14) | 0.0397 (8) | 0.0414 (9) | 0.0282 (8) | −0.0011 (8) | −0.0074 (6) |
O6 | 0.0610 (9) | 0.0305 (7) | 0.0485 (8) | 0.0107 (6) | 0.0025 (7) | −0.0063 (6) |
N3 | 0.0479 (10) | 0.0271 (7) | 0.0316 (8) | 0.0024 (6) | 0.0031 (7) | −0.0017 (6) |
C21 | 0.0401 (11) | 0.0308 (9) | 0.0330 (10) | 0.0023 (7) | −0.0005 (8) | 0.0036 (7) |
N4 | 0.0545 (11) | 0.0441 (9) | 0.0307 (9) | 0.0005 (7) | 0.0023 (7) | 0.0013 (7) |
C23 | 0.0561 (13) | 0.0559 (13) | 0.0332 (11) | 0.0003 (10) | 0.0026 (9) | 0.0088 (9) |
C24 | 0.0473 (12) | 0.0451 (11) | 0.0479 (12) | −0.0036 (9) | 0.0014 (10) | 0.0175 (9) |
C25 | 0.0416 (11) | 0.0301 (9) | 0.0503 (12) | −0.0004 (8) | −0.0018 (9) | 0.0051 (8) |
C26 | 0.0316 (10) | 0.0288 (8) | 0.0373 (10) | 0.0006 (7) | −0.0002 (8) | 0.0001 (7) |
C27 | 0.0369 (10) | 0.0291 (9) | 0.0392 (10) | −0.0010 (7) | −0.0019 (8) | −0.0042 (7) |
C28 | 0.0424 (10) | 0.0265 (8) | 0.0324 (9) | 0.0014 (7) | −0.0010 (8) | −0.0018 (7) |
C29 | 0.0632 (13) | 0.0293 (9) | 0.0310 (10) | 0.0043 (9) | −0.0030 (9) | 0.0000 (8) |
C30 | 0.0805 (17) | 0.0383 (11) | 0.0418 (12) | −0.0025 (10) | 0.0081 (11) | 0.0017 (9) |
C31 | 0.133 (3) | 0.0419 (12) | 0.0476 (14) | −0.0040 (14) | 0.0228 (16) | 0.0059 (11) |
C32 | 0.170 (4) | 0.0582 (17) | 0.0487 (16) | 0.028 (2) | −0.001 (2) | 0.0197 (13) |
C33 | 0.119 (3) | 0.086 (2) | 0.0635 (18) | 0.035 (2) | −0.0273 (18) | 0.0165 (16) |
C34 | 0.0714 (17) | 0.0604 (14) | 0.0548 (14) | 0.0069 (12) | −0.0152 (12) | 0.0078 (11) |
C35 | 0.0615 (14) | 0.0312 (9) | 0.0346 (10) | 0.0008 (9) | 0.0086 (9) | −0.0022 (8) |
C36 | 0.0666 (16) | 0.0621 (14) | 0.0587 (15) | 0.0074 (12) | 0.0179 (12) | 0.0076 (12) |
C37 | 0.111 (3) | 0.093 (2) | 0.077 (2) | 0.0220 (19) | 0.053 (2) | 0.0210 (18) |
C38 | 0.171 (4) | 0.116 (3) | 0.0408 (17) | 0.009 (3) | 0.033 (2) | 0.0017 (17) |
C39 | 0.144 (3) | 0.137 (3) | 0.0400 (16) | −0.025 (3) | 0.0044 (18) | −0.0144 (18) |
C40 | 0.0865 (19) | 0.0826 (18) | 0.0381 (13) | −0.0191 (15) | 0.0032 (12) | −0.0114 (12) |
S1—O1 | 1.4309 (16) | S2—O4 | 1.4349 (16) |
S1—O2 | 1.4289 (16) | S2—O5 | 1.4268 (15) |
S1—C1 | 1.7776 (18) | S2—C21 | 1.7762 (18) |
S1—C8 | 1.8085 (19) | S2—C28 | 1.8037 (18) |
O3—C7 | 1.222 (2) | O6—C27 | 1.218 (2) |
N1—C7 | 1.364 (2) | N3—C27 | 1.364 (2) |
N1—C8 | 1.466 (2) | N3—C28 | 1.473 (2) |
N1—C15 | 1.459 (2) | N3—C35 | 1.447 (2) |
C1—N2 | 1.331 (2) | C21—N4 | 1.327 (2) |
C1—C6 | 1.386 (3) | C21—C26 | 1.386 (2) |
N2—C3 | 1.336 (3) | N4—C23 | 1.329 (2) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C3—C4 | 1.373 (3) | C23—C24 | 1.383 (3) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C4—C5 | 1.386 (3) | C24—C25 | 1.379 (3) |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C5—C6 | 1.395 (2) | C25—C26 | 1.389 (2) |
C6—C7 | 1.506 (3) | C26—C27 | 1.510 (3) |
C8—H8 | 0.9800 | C28—H28 | 0.9800 |
C8—C9 | 1.503 (2) | C28—C29 | 1.510 (2) |
C9—C10 | 1.390 (3) | C29—C30 | 1.379 (3) |
C9—C14 | 1.377 (3) | C29—C34 | 1.390 (3) |
C10—H10 | 0.9300 | C30—H30 | 0.9300 |
C10—C11 | 1.376 (3) | C30—C31 | 1.383 (3) |
C11—H11 | 0.9300 | C31—H31 | 0.9300 |
C11—C12 | 1.372 (3) | C31—C32 | 1.365 (4) |
C12—H12 | 0.9300 | C32—H32 | 0.9300 |
C12—C13 | 1.372 (3) | C32—C33 | 1.367 (4) |
C13—H13 | 0.9300 | C33—H33 | 0.9300 |
C13—C14 | 1.383 (3) | C33—C34 | 1.382 (3) |
C14—H14 | 0.9300 | C34—H34 | 0.9300 |
C15—C16 | 1.367 (3) | C35—C36 | 1.372 (3) |
C15—C20 | 1.379 (3) | C35—C40 | 1.366 (3) |
C16—H16 | 0.9300 | C36—H36 | 0.9300 |
C16—C17 | 1.387 (3) | C36—C37 | 1.397 (4) |
C17—H17 | 0.9300 | C37—H37 | 0.9300 |
C17—C18 | 1.356 (4) | C37—C38 | 1.375 (5) |
C18—H18 | 0.9300 | C38—H38 | 0.9300 |
C18—C19 | 1.370 (4) | C38—C39 | 1.353 (5) |
C19—H19 | 0.9300 | C39—H39 | 0.9300 |
C19—C20 | 1.397 (3) | C39—C40 | 1.382 (4) |
C20—H20 | 0.9300 | C40—H40 | 0.9300 |
O1—S1—C1 | 108.86 (9) | O4—S2—C21 | 108.44 (8) |
O1—S1—C8 | 111.01 (9) | O4—S2—C28 | 111.03 (9) |
O2—S1—O1 | 119.48 (10) | O5—S2—O4 | 119.14 (10) |
O2—S1—C1 | 109.82 (9) | O5—S2—C21 | 109.50 (9) |
O2—S1—C8 | 108.66 (9) | O5—S2—C28 | 108.74 (9) |
C1—S1—C8 | 96.59 (8) | C21—S2—C28 | 97.89 (8) |
C7—N1—C8 | 119.92 (15) | C27—N3—C28 | 120.15 (15) |
C7—N1—C15 | 118.80 (14) | C27—N3—C35 | 118.72 (14) |
C15—N1—C8 | 119.39 (13) | C35—N3—C28 | 118.90 (14) |
N2—C1—S1 | 116.15 (14) | N4—C21—S2 | 115.57 (13) |
N2—C1—C6 | 126.13 (17) | N4—C21—C26 | 126.60 (16) |
C6—C1—S1 | 117.72 (14) | C26—C21—S2 | 117.81 (14) |
C1—N2—C3 | 115.68 (18) | C21—N4—C23 | 115.95 (16) |
N2—C3—H3 | 118.0 | N4—C23—H23 | 118.4 |
N2—C3—C4 | 123.90 (19) | N4—C23—C24 | 123.15 (19) |
C4—C3—H3 | 118.0 | C24—C23—H23 | 118.4 |
C3—C4—H4 | 120.5 | C23—C24—H24 | 120.4 |
C3—C4—C5 | 119.07 (18) | C25—C24—C23 | 119.26 (17) |
C5—C4—H4 | 120.5 | C25—C24—H24 | 120.4 |
C4—C5—H5 | 120.5 | C24—C25—H25 | 120.3 |
C4—C5—C6 | 118.94 (19) | C24—C25—C26 | 119.32 (17) |
C6—C5—H5 | 120.5 | C26—C25—H25 | 120.3 |
C1—C6—C5 | 116.27 (17) | C21—C26—C25 | 115.71 (17) |
C1—C6—C7 | 125.04 (15) | C21—C26—C27 | 124.67 (15) |
C5—C6—C7 | 118.58 (16) | C25—C26—C27 | 119.46 (16) |
O3—C7—N1 | 122.41 (17) | O6—C27—N3 | 122.22 (17) |
O3—C7—C6 | 119.79 (15) | O6—C27—C26 | 119.29 (16) |
N1—C7—C6 | 117.77 (15) | N3—C27—C26 | 118.39 (15) |
S1—C8—H8 | 107.5 | S2—C28—H28 | 107.6 |
N1—C8—S1 | 108.82 (12) | N3—C28—S2 | 107.80 (12) |
N1—C8—H8 | 107.5 | N3—C28—H28 | 107.6 |
N1—C8—C9 | 115.31 (14) | N3—C28—C29 | 115.84 (15) |
C9—C8—S1 | 109.85 (12) | C29—C28—S2 | 110.23 (12) |
C9—C8—H8 | 107.5 | C29—C28—H28 | 107.6 |
C10—C9—C8 | 122.03 (16) | C30—C29—C28 | 123.24 (19) |
C14—C9—C8 | 118.21 (16) | C30—C29—C34 | 119.20 (19) |
C14—C9—C10 | 119.72 (17) | C34—C29—C28 | 117.46 (19) |
C9—C10—H10 | 120.1 | C29—C30—H30 | 119.9 |
C11—C10—C9 | 119.8 (2) | C29—C30—C31 | 120.2 (2) |
C11—C10—H10 | 120.1 | C31—C30—H30 | 119.9 |
C10—C11—H11 | 119.8 | C30—C31—H31 | 119.8 |
C12—C11—C10 | 120.4 (2) | C32—C31—C30 | 120.3 (3) |
C12—C11—H11 | 119.8 | C32—C31—H31 | 119.8 |
C11—C12—H12 | 120.0 | C31—C32—H32 | 119.9 |
C11—C12—C13 | 120.03 (19) | C31—C32—C33 | 120.1 (3) |
C13—C12—H12 | 120.0 | C33—C32—H32 | 119.9 |
C12—C13—H13 | 119.9 | C32—C33—H33 | 119.8 |
C12—C13—C14 | 120.3 (2) | C32—C33—C34 | 120.4 (3) |
C14—C13—H13 | 119.9 | C34—C33—H33 | 119.8 |
C9—C14—C13 | 119.8 (2) | C29—C34—H34 | 120.1 |
C9—C14—H14 | 120.1 | C33—C34—C29 | 119.8 (3) |
C13—C14—H14 | 120.1 | C33—C34—H34 | 120.1 |
C16—C15—N1 | 119.61 (18) | C36—C35—N3 | 119.09 (19) |
C16—C15—C20 | 120.9 (2) | C40—C35—N3 | 119.53 (19) |
C20—C15—N1 | 119.38 (18) | C40—C35—C36 | 121.4 (2) |
C15—C16—H16 | 120.4 | C35—C36—H36 | 120.6 |
C15—C16—C17 | 119.2 (2) | C35—C36—C37 | 118.7 (3) |
C17—C16—H16 | 120.4 | C37—C36—H36 | 120.6 |
C16—C17—H17 | 119.7 | C36—C37—H37 | 120.2 |
C18—C17—C16 | 120.6 (3) | C38—C37—C36 | 119.6 (3) |
C18—C17—H17 | 119.7 | C38—C37—H37 | 120.2 |
C17—C18—H18 | 119.7 | C37—C38—H38 | 119.8 |
C17—C18—C19 | 120.5 (2) | C39—C38—C37 | 120.4 (3) |
C19—C18—H18 | 119.7 | C39—C38—H38 | 119.8 |
C18—C19—H19 | 120.1 | C38—C39—H39 | 119.6 |
C18—C19—C20 | 119.8 (3) | C38—C39—C40 | 120.8 (3) |
C20—C19—H19 | 120.1 | C40—C39—H39 | 119.6 |
C15—C20—C19 | 118.9 (2) | C35—C40—C39 | 119.0 (3) |
C15—C20—H20 | 120.5 | C35—C40—H40 | 120.5 |
C19—C20—H20 | 120.5 | C39—C40—H40 | 120.5 |
S1—C1—N2—C3 | 179.14 (15) | S2—C21—N4—C23 | 177.70 (14) |
S1—C1—C6—C5 | −179.38 (14) | S2—C21—C26—C25 | −178.19 (14) |
S1—C1—C6—C7 | 4.6 (3) | S2—C21—C26—C27 | −2.7 (2) |
S1—C8—C9—C10 | 64.1 (2) | S2—C28—C29—C30 | −56.3 (2) |
S1—C8—C9—C14 | −113.40 (17) | S2—C28—C29—C34 | 119.99 (18) |
O1—S1—C1—N2 | 97.46 (17) | O4—S2—C21—N4 | −95.33 (16) |
O1—S1—C1—C6 | −82.47 (16) | O4—S2—C21—C26 | 82.93 (16) |
O1—S1—C8—N1 | 52.60 (14) | O4—S2—C28—N3 | −53.75 (14) |
O1—S1—C8—C9 | −74.51 (14) | O4—S2—C28—C29 | 73.56 (15) |
O2—S1—C1—N2 | −35.07 (19) | O5—S2—C21—N4 | 36.17 (18) |
O2—S1—C1—C6 | 145.00 (15) | O5—S2—C21—C26 | −145.57 (15) |
O2—S1—C8—N1 | −174.07 (12) | O5—S2—C28—N3 | 173.30 (12) |
O2—S1—C8—C9 | 58.82 (15) | O5—S2—C28—C29 | −59.39 (16) |
N1—C8—C9—C10 | −59.3 (2) | N3—C28—C29—C30 | 66.4 (2) |
N1—C8—C9—C14 | 123.22 (18) | N3—C28—C29—C34 | −117.3 (2) |
N1—C15—C16—C17 | 174.64 (19) | N3—C35—C36—C37 | 176.9 (2) |
N1—C15—C20—C19 | −175.11 (19) | N3—C35—C40—C39 | −177.0 (2) |
C1—S1—C8—N1 | −60.54 (13) | C21—S2—C28—N3 | 59.54 (13) |
C1—S1—C8—C9 | 172.35 (13) | C21—S2—C28—C29 | −173.14 (14) |
C1—N2—C3—C4 | 0.1 (3) | C21—N4—C23—C24 | 0.9 (3) |
C1—C6—C7—O3 | 157.04 (18) | C21—C26—C27—O6 | −159.73 (18) |
C1—C6—C7—N1 | −20.8 (3) | C21—C26—C27—N3 | 16.7 (3) |
N2—C1—C6—C5 | 0.7 (3) | N4—C21—C26—C25 | −0.1 (3) |
N2—C1—C6—C7 | −175.37 (18) | N4—C21—C26—C27 | 175.31 (18) |
N2—C3—C4—C5 | 0.9 (3) | N4—C23—C24—C25 | −0.9 (3) |
C3—C4—C5—C6 | −1.1 (3) | C23—C24—C25—C26 | 0.4 (3) |
C4—C5—C6—C1 | 0.4 (3) | C24—C25—C26—C21 | 0.1 (3) |
C4—C5—C6—C7 | 176.70 (17) | C24—C25—C26—C27 | −175.55 (17) |
C5—C6—C7—O3 | −18.9 (3) | C25—C26—C27—O6 | 15.6 (3) |
C5—C6—C7—N1 | 163.18 (16) | C25—C26—C27—N3 | −167.98 (16) |
C6—C1—N2—C3 | −0.9 (3) | C26—C21—N4—C23 | −0.4 (3) |
C7—N1—C8—S1 | 57.44 (18) | C27—N3—C28—S2 | −58.41 (19) |
C7—N1—C8—C9 | −178.63 (15) | C27—N3—C28—C29 | 177.60 (16) |
C7—N1—C15—C16 | 99.0 (2) | C27—N3—C35—C36 | 89.0 (2) |
C7—N1—C15—C20 | −84.2 (2) | C27—N3—C35—C40 | −92.1 (2) |
C8—S1—C1—N2 | −147.65 (16) | C28—S2—C21—N4 | 149.32 (15) |
C8—S1—C1—C6 | 32.42 (16) | C28—S2—C21—C26 | −32.42 (16) |
C8—N1—C7—O3 | 167.93 (17) | C28—N3—C27—O6 | −165.63 (17) |
C8—N1—C7—C6 | −14.3 (2) | C28—N3—C27—C26 | 18.0 (2) |
C8—N1—C15—C16 | −65.4 (2) | C28—N3—C35—C36 | −107.9 (2) |
C8—N1—C15—C20 | 111.5 (2) | C28—N3—C35—C40 | 70.9 (2) |
C8—C9—C10—C11 | −178.63 (18) | C28—C29—C30—C31 | 175.96 (19) |
C8—C9—C14—C13 | 178.46 (19) | C28—C29—C34—C33 | −176.8 (2) |
C9—C10—C11—C12 | 0.7 (3) | C29—C30—C31—C32 | 0.6 (4) |
C10—C9—C14—C13 | 0.9 (3) | C30—C29—C34—C33 | −0.4 (3) |
C10—C11—C12—C13 | 0.0 (3) | C30—C31—C32—C33 | −0.2 (4) |
C11—C12—C13—C14 | −0.3 (4) | C31—C32—C33—C34 | −0.4 (5) |
C12—C13—C14—C9 | −0.2 (3) | C32—C33—C34—C29 | 0.7 (4) |
C14—C9—C10—C11 | −1.2 (3) | C34—C29—C30—C31 | −0.3 (3) |
C15—N1—C7—O3 | 3.7 (3) | C35—N3—C27—O6 | −2.8 (3) |
C15—N1—C7—C6 | −178.52 (15) | C35—N3—C27—C26 | −179.13 (16) |
C15—N1—C8—S1 | −138.38 (14) | C35—N3—C28—S2 | 138.78 (14) |
C15—N1—C8—C9 | −14.5 (2) | C35—N3—C28—C29 | 14.8 (2) |
C15—C16—C17—C18 | 1.1 (4) | C35—C36—C37—C38 | 0.3 (4) |
C16—C15—C20—C19 | 1.7 (3) | C36—C35—C40—C39 | 1.9 (4) |
C16—C17—C18—C19 | 0.4 (4) | C36—C37—C38—C39 | 1.3 (5) |
C17—C18—C19—C20 | −0.9 (4) | C37—C38—C39—C40 | −1.4 (6) |
C18—C19—C20—C15 | −0.2 (3) | C38—C39—C40—C35 | −0.2 (5) |
C20—C15—C16—C17 | −2.2 (3) | C40—C35—C36—C37 | −1.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.93 | 2.56 | 3.234 (3) | 130 |
C5—H5···O4ii | 0.93 | 2.69 | 3.388 (2) | 132 |
C8—H8···O6ii | 0.98 | 2.31 | 3.089 (2) | 136 |
C16—H16···O6ii | 0.93 | 2.71 | 3.466 (3) | 139 |
C20—H20···O6 | 0.93 | 2.70 | 3.496 (3) | 145 |
C25—H25···O1 | 0.93 | 2.75 | 3.463 (3) | 135 |
C28—H28···O3 | 0.98 | 2.37 | 3.126 (2) | 134 |
C36—H36···O3iii | 0.93 | 2.64 | 3.381 (3) | 137 |
C40—H40···O3 | 0.93 | 2.68 | 3.439 (3) | 140 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, y, z. |
Funding information
Research reported here was conducted on instrumentation funded by National Science Foundation: CHEM-0131112 for the Bruker AXS diffractometer, and SIG S10 grants of the National Institutes of Health under award numbers 1S10OD028589–01 and 1S10RR023439–01, for the Rigaku diffraction system to Dr Neela Yennawar.
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