research communications
Crystal structures of two solvated 2-aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones
aDepartment of Biochemistry and Molecular Biology, 108 Althouse Laboratory, Pennsylvania State University, University Park, PA 16802, USA, and bPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
*Correspondence e-mail: ljs43@psu.edu
The synthesis and crystal structures of 2-(4-fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one toluene hemisolvate (1), C19H13FN2OS·0.5C7H8, and 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one isopropanol 0.25-solvate 0.0625-hydrate (2), C19H13N3O3S·0.25C3H7O·0.0625H2O, are reported. Both are racemic mixtures (centrosymmetric crystal structures) of the individual compounds and incorporate solvent molecules in their structures. Compound 2 has four thiazine molecules in the All the thiazine rings in this study show an envelope pucker, with the C atom bearing the substituted phenyl ring displaced from the other atoms. The phenyl and aryl rings in each of the molecules are roughly orthogonal to each other, with dihedral angles of about 75°. The extended structures of 1 and 2 are consolidated by C—H⋯O and C—H⋯N(π), as well as T-type (C—H⋯π) interactions. Parallel aromatic ring interactions (π–π stacking) are observed only in 2.
1. Chemical context
Compounds with a 2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one scaffold have shown anticancer (Arya et al., 2014), antibacterial (Shreedhara et al., 2017), and glycosidase inhibitory (Li et al., 2012) bioactivity. These compounds feature a pyridine ring fused to a thiazine ring. Previously, we reported the synthesis and structure of 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (Yennawar et al., 2014). Herein, we report the syntheses and structures of two solvated analogs containing a substituent on the C-phenyl ring: 2-(4-fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one as a toluene hemisolvate, 1, and 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one as a mixed propanol–water solvate, 2.
2. Structural commentary
The 1 (Fig. 1) comprises the title molecule along with the solvent molecule (toluene) straddling an inversion center. The 1,3-thiazine ring is in an envelope pucker conformation according to the puckering parameters [Q = 0.6016 (16) Å, θ = 115.35 (16)°, and φ = 220.50 (18)°] calculated by PLATON (Spek, 2009), with atom C1 displaced from the other atoms. The phenyl rings on the 2 and 3 positions of the thiazine ring are close to orthogonal, forming a dihedral angle of 77.65 (10)°; their dihedral angles with respect to the N2 pyridine ring are 81.45 (11) and 79.22 (9)°, respectively. Atom C1 is a stereogenic center; in the arbitrarily chosen it has an S configuration, but crystal symmetry generates a racemic mixture.
ofIn 2, the configurations of the stereogenic centers in the four arbitrarily chosen independent thiazine molecules A, B, C, and D (Fig. 2) are R at C1 and C39, and S at C20 and C58. A solvent molecule of 2-propanol and a water molecule with partial (0.25) occupancy complete the The puckering of the thiazine ring in each case is an envelope (Q ∼ 55 Å, θ ∼ 65°, and φ ∼ 41°, considering tranformations), which is very similar to that in 1. The four molecules within this structure are all very similar in their three-dimensional dispositions, as can be seen in the overlay figure (Fig. 3). For the X (pyridine C3–C7/N2), Y (phenyl C8–C13), and Z (para-nitrophenyl C14–C19) rings in molecule A, the X/Y, X/Z, and Y/Z dihedral angles are 70.52 (16), 87.25 (14), and 89.09 (16)°, respectively. Equivalent data for molecule B are 83.73 (16), 86.23 (14) and 77.44 (16)°, respectively; for molecule C are 65.92 (17), 85.94 (14), and 85.84 (17)°, respectively; for molecule D are 85.84 (18), 82.77 (14), and 77.72 (18)°, respectively. The superimposition of the structures of 1 and 2 (Fig. 4) also shows very little discrepancy.
3. Supramolecular features
The 1 has the chiral C atom (C1) participating in a C—H⋯π-type interaction with the toluene ring [C—H⋯π = 3.735 (3) Å, 142°]. The O atom on the fused thiazine ring system accepts a C—H⋯O hydrogen bond from a symmetry-related pyridine ring in a parallel-reciprocal fashion (Table 1 and Fig. 5). Some other weak C—H⋯π interactions may help to consolidate the structure. The aryl and pyridyl rings of symmetry-related molecules exhibit a T-type interaction. No π–π parallel stacking is observed in this structure.
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Within the 2 the `3-phenyl rings' of neighboring enantiomeric molecules (two pairs) exhibit a parallel stacking interaction. One of the four phenyl rings participates in a C—H⋯O-type interaction with the partially occupied water O atom (Table 2). The chiral C atom of molecule A participates in a C—H⋯O hydrogen bond with the O atom of the solvent 2-propanol molecule. The extended packing (Fig. 6) shows neighboring molecules interacting via parallel stacking interactions between the phenyl rings, as well as between the aryl and pyridyl rings. The T-type ring interactions are also observed between the phenyl and aryl rings, as well as between the pyridyl rings of neighboring molecules. Various C—H⋯O, O—H⋯O, and C—H⋯N type hydrogen bonds consolidate the structure.
of4. Database survey
Along with the previously mentioned structure (Yennawar et al., 2014), we have published a structure of the sulfoxide derivative (Yennawar et al. 2017). No other similar structures were found.
5. Synthesis and crystallization
For the preparation of 2-(4-fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (1), a two-necked 25 ml round-bottomed flask was oven-dried, cooled under N2, and a stir bar was added. The flask was charged with aniline (0.559 g, 6 mmol) and 4-fluorobenzaldehyde (0.744 g, 6 mmol), and stirred for 5 min. Thionicotinic acid (0.931 g, 6 mmol) and 2-methyltetrahydrofuran (2.3 ml) were added. Pyridine (1.95 ml, 24 mmol) was added and, finally, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) in 2-methyltetrahydrofuran (50 wt%; 7.3 ml, 12 mmol) was added. The reaction was stirred at room temperature, followed by (TLC), and then poured into a separatory funnel with dichloromethane (20 ml). The mixture was washed with water (10 ml). The aqueous fraction was then extracted twice with dichloromethane (10 ml each). The organics were combined and washed with saturated sodium bicarbonate (10 ml) and then saturated sodium chloride (10 ml). The organic fraction was dried over sodium sulfate and concentrated under vacuum to give a crude mixture, which was chromatographed on 30 g flash silica gel with mixtures of ethyl acetate and hexanes (30 to 70% ethyl acetate) to give a solid. Recrystallization from a solvent mixture of toluene and hexanes gave colorless crystals of 1 (yield 0.5705 g, 28%; m.p. 127.2–127.4 °C).
2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one (2) was prepared by the same method with 1-(4-nitrophenyl)-N-phenylmethanimine (1.35 g, 6 mmol) replacing aniline and 4-fluorobenzaldehyde. The crude solid after the extractive workup was recrystallized from a 2-propanol solution to give colorless crystals of 2 (yield 1.3581 g, 62%; m.p. 119–121 °C).
6. Refinement
Crystal data, data collection and structure . H atoms were positioned geometrically (C—H = 0.93–0.98 Å and O—H = 0.82 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C,O).
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S2056989019013781/hb7856sup1.cif
contains datablocks global, 2, 1. DOI:Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989019013781/hb78562sup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019013781/hb78561sup4.mol
Supporting information file. DOI: https://doi.org/10.1107/S2056989019013781/hb78562sup5.mol
Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989019013781/hb78561sup6.hkl
For both structures, data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C19H13FN2OS·0.5C7H8 | F(000) = 796 |
Mr = 382.44 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.4481 (16) Å | Cell parameters from 4037 reflections |
b = 9.0141 (10) Å | θ = 2.5–28.1° |
c = 16.3427 (19) Å | µ = 0.19 mm−1 |
β = 115.481 (2)° | T = 298 K |
V = 1921.4 (4) Å3 | Block, colorless |
Z = 4 | 0.27 × 0.26 × 0.26 mm |
Bruker CCD area detector diffractometer | 4590 independent reflections |
Radiation source: fine-focus sealed tube | 3093 reflections with I > 2σ(I) |
Parallel-graphite monochromator | Rint = 0.026 |
Detector resolution: 8.34 pixels mm-1 | θmax = 28.3°, θmin = 1.6° |
phi and ω scans | h = −18→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | k = −11→11 |
Tmin = 0.877, Tmax = 0.9 | l = −21→20 |
14808 measured reflections |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0821P)2 + 0.1824P] where P = (Fo2 + 2Fc2)/3 |
4590 reflections | (Δ/σ)max < 0.001 |
266 parameters | Δρmax = 0.27 e Å−3 |
57 restraints | Δρmin = −0.22 e Å−3 |
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. |
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 > 2sigma(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) | |
C1 | 0.29551 (12) | 0.63383 (19) | 0.57705 (12) | 0.0532 (4) | |
H1 | 0.3212 | 0.5451 | 0.5589 | 0.064* | |
C2 | 0.15230 (13) | 0.8065 (2) | 0.49787 (11) | 0.0556 (4) | |
C3 | 0.21206 (12) | 0.92059 (18) | 0.56667 (11) | 0.0507 (4) | |
C4 | 0.31888 (13) | 0.9229 (2) | 0.61149 (12) | 0.0547 (4) | |
C5 | 0.32028 (19) | 1.1473 (2) | 0.67453 (17) | 0.0801 (6) | |
H5 | 0.3569 | 1.2267 | 0.7100 | 0.096* | |
C6 | 0.21563 (18) | 1.1539 (2) | 0.63701 (15) | 0.0706 (5) | |
H6 | 0.1823 | 1.2334 | 0.6490 | 0.085* | |
C7 | 0.16061 (14) | 1.0401 (2) | 0.58099 (12) | 0.0589 (4) | |
H7 | 0.0894 | 1.0435 | 0.5529 | 0.071* | |
C8 | 0.28175 (12) | 0.59127 (17) | 0.66097 (11) | 0.0504 (4) | |
C9 | 0.36712 (13) | 0.5528 (2) | 0.73966 (13) | 0.0624 (5) | |
H9 | 0.4317 | 0.5558 | 0.7402 | 0.075* | |
C10 | 0.35817 (17) | 0.5105 (2) | 0.81643 (14) | 0.0739 (6) | |
H10 | 0.4158 | 0.4854 | 0.8688 | 0.089* | |
C11 | 0.26220 (19) | 0.5060 (2) | 0.81421 (15) | 0.0738 (6) | |
C12 | 0.17612 (16) | 0.5385 (2) | 0.73843 (16) | 0.0733 (6) | |
H12 | 0.1118 | 0.5319 | 0.7383 | 0.088* | |
C13 | 0.18591 (13) | 0.5816 (2) | 0.66148 (14) | 0.0613 (5) | |
H13 | 0.1275 | 0.6046 | 0.6092 | 0.074* | |
C14 | 0.15587 (12) | 0.5691 (2) | 0.42719 (11) | 0.0550 (4) | |
C15 | 0.13424 (15) | 0.6091 (2) | 0.33997 (13) | 0.0666 (5) | |
H15 | 0.1450 | 0.7063 | 0.3270 | 0.080* | |
C16 | 0.09640 (17) | 0.5050 (3) | 0.27128 (14) | 0.0786 (6) | |
H16 | 0.0807 | 0.5330 | 0.2120 | 0.094* | |
C17 | 0.08185 (15) | 0.3616 (3) | 0.28964 (16) | 0.0788 (6) | |
H17 | 0.0575 | 0.2918 | 0.2433 | 0.095* | |
C18 | 0.10316 (18) | 0.3212 (3) | 0.37627 (17) | 0.0835 (6) | |
H18 | 0.0932 | 0.2235 | 0.3890 | 0.100* | |
C19 | 0.13963 (17) | 0.4250 (2) | 0.44561 (14) | 0.0748 (6) | |
H19 | 0.1531 | 0.3972 | 0.5045 | 0.090* | |
F1 | 0.25250 (13) | 0.46699 (18) | 0.89080 (11) | 0.1126 (5) | |
N1 | 0.20053 (10) | 0.67498 (16) | 0.49958 (9) | 0.0557 (4) | |
N2 | 0.37270 (13) | 1.03462 (19) | 0.66340 (13) | 0.0728 (5) | |
O1 | 0.06489 (10) | 0.83185 (16) | 0.44210 (9) | 0.0744 (4) | |
S1 | 0.39249 (3) | 0.77650 (6) | 0.60028 (4) | 0.06511 (19) | |
C1A | 0.4323 (6) | 0.2876 (5) | 0.5316 (6) | 0.246 (7) | 0.50 |
H1AA | 0.4597 | 0.2762 | 0.5962 | 0.369* | 0.50 |
H1AB | 0.4497 | 0.2024 | 0.5059 | 0.369* | 0.50 |
H1AC | 0.3591 | 0.2969 | 0.5067 | 0.369* | 0.50 |
C1B | 0.4768 (3) | 0.4249 (4) | 0.5097 (4) | 0.0998 (16) | 0.50 |
C1C | 0.5654 (3) | 0.4916 (6) | 0.5751 (3) | 0.113 (4) | 0.50 |
H1C | 0.5980 | 0.4492 | 0.6324 | 0.136* | 0.50 |
C1D | 0.6056 (4) | 0.6207 (6) | 0.5558 (5) | 0.136 (3) | 0.50 |
H1D | 0.6644 | 0.6636 | 0.6000 | 0.163* | 0.50 |
C1E | 0.5576 (6) | 0.6857 (4) | 0.4700 (5) | 0.161 (4) | 0.50 |
H1E | 0.5842 | 0.7718 | 0.4570 | 0.193* | 0.50 |
C1F | 0.4695 (5) | 0.6202 (6) | 0.4041 (4) | 0.158 (4) | 0.50 |
H1F | 0.4373 | 0.6627 | 0.3468 | 0.190* | 0.50 |
C1G | 0.4298 (4) | 0.4911 (6) | 0.4239 (3) | 0.136 (5) | 0.50 |
H1G | 0.3711 | 0.4484 | 0.3795 | 0.163* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0436 (8) | 0.0512 (10) | 0.0595 (10) | 0.0101 (7) | 0.0170 (7) | −0.0053 (8) |
C2 | 0.0517 (9) | 0.0555 (10) | 0.0561 (10) | 0.0126 (8) | 0.0199 (8) | 0.0024 (8) |
C3 | 0.0547 (9) | 0.0457 (9) | 0.0540 (9) | 0.0081 (7) | 0.0255 (7) | 0.0040 (7) |
C4 | 0.0544 (9) | 0.0493 (10) | 0.0654 (10) | −0.0003 (7) | 0.0305 (8) | 0.0016 (8) |
C5 | 0.0924 (16) | 0.0543 (12) | 0.0949 (16) | −0.0173 (11) | 0.0413 (13) | −0.0139 (11) |
C6 | 0.0978 (15) | 0.0452 (11) | 0.0830 (13) | 0.0065 (10) | 0.0523 (12) | −0.0023 (9) |
C7 | 0.0667 (11) | 0.0530 (10) | 0.0640 (11) | 0.0125 (8) | 0.0347 (9) | 0.0074 (8) |
C8 | 0.0455 (8) | 0.0399 (9) | 0.0597 (9) | 0.0051 (6) | 0.0169 (7) | −0.0067 (7) |
C9 | 0.0474 (9) | 0.0641 (12) | 0.0662 (11) | 0.0045 (8) | 0.0152 (8) | −0.0017 (9) |
C10 | 0.0749 (13) | 0.0709 (13) | 0.0617 (12) | 0.0033 (10) | 0.0159 (10) | 0.0035 (10) |
C11 | 0.1004 (16) | 0.0569 (12) | 0.0735 (13) | 0.0014 (11) | 0.0463 (13) | −0.0014 (9) |
C12 | 0.0716 (13) | 0.0608 (13) | 0.1025 (16) | 0.0028 (10) | 0.0515 (12) | −0.0017 (11) |
C13 | 0.0476 (9) | 0.0563 (11) | 0.0754 (12) | 0.0080 (8) | 0.0221 (8) | −0.0024 (9) |
C14 | 0.0494 (9) | 0.0543 (10) | 0.0550 (10) | 0.0088 (7) | 0.0166 (7) | −0.0053 (8) |
C15 | 0.0721 (12) | 0.0670 (12) | 0.0653 (12) | 0.0066 (9) | 0.0339 (10) | −0.0018 (9) |
C16 | 0.0800 (14) | 0.0959 (18) | 0.0593 (12) | 0.0108 (12) | 0.0295 (10) | −0.0122 (11) |
C17 | 0.0637 (12) | 0.0876 (17) | 0.0733 (14) | 0.0048 (11) | 0.0183 (10) | −0.0297 (12) |
C18 | 0.0901 (16) | 0.0613 (13) | 0.0875 (16) | −0.0057 (11) | 0.0271 (12) | −0.0150 (11) |
C19 | 0.0892 (14) | 0.0607 (13) | 0.0625 (12) | 0.0023 (10) | 0.0212 (11) | −0.0022 (9) |
F1 | 0.1540 (14) | 0.1109 (12) | 0.0960 (10) | −0.0009 (10) | 0.0757 (10) | 0.0084 (8) |
N1 | 0.0519 (7) | 0.0490 (8) | 0.0560 (8) | 0.0110 (6) | 0.0135 (6) | −0.0051 (6) |
N2 | 0.0672 (10) | 0.0594 (10) | 0.0908 (12) | −0.0135 (8) | 0.0331 (9) | −0.0106 (9) |
O1 | 0.0562 (7) | 0.0767 (9) | 0.0685 (8) | 0.0241 (6) | 0.0063 (6) | −0.0078 (7) |
S1 | 0.0459 (3) | 0.0666 (3) | 0.0863 (4) | 0.0046 (2) | 0.0318 (2) | −0.0013 (2) |
C1A | 0.304 (18) | 0.126 (9) | 0.42 (2) | −0.023 (10) | 0.256 (17) | 0.003 (11) |
C1B | 0.121 (4) | 0.067 (3) | 0.156 (5) | 0.026 (3) | 0.102 (4) | −0.001 (3) |
C1C | 0.128 (10) | 0.109 (7) | 0.124 (6) | 0.021 (6) | 0.075 (5) | −0.025 (5) |
C1D | 0.126 (5) | 0.107 (5) | 0.228 (8) | −0.018 (4) | 0.128 (6) | −0.053 (5) |
C1E | 0.259 (12) | 0.059 (4) | 0.296 (11) | 0.024 (5) | 0.244 (10) | 0.012 (6) |
C1F | 0.280 (11) | 0.092 (5) | 0.167 (6) | 0.087 (6) | 0.157 (6) | 0.045 (4) |
C1G | 0.127 (10) | 0.130 (9) | 0.151 (8) | 0.061 (6) | 0.060 (6) | −0.004 (6) |
C1—H1 | 0.9800 | C14—C15 | 1.370 (3) |
C1—C8 | 1.517 (2) | C14—C19 | 1.376 (3) |
C1—N1 | 1.459 (2) | C14—N1 | 1.439 (2) |
C1—S1 | 1.8176 (18) | C15—H15 | 0.9300 |
C2—C3 | 1.494 (2) | C15—C16 | 1.383 (3) |
C2—N1 | 1.370 (2) | C16—H16 | 0.9300 |
C2—O1 | 1.219 (2) | C16—C17 | 1.363 (3) |
C3—C4 | 1.395 (2) | C17—H17 | 0.9300 |
C3—C7 | 1.385 (2) | C17—C18 | 1.363 (3) |
C4—N2 | 1.331 (2) | C18—H18 | 0.9300 |
C4—S1 | 1.7534 (18) | C18—C19 | 1.387 (3) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.367 (3) | C1A—H1AA | 0.9600 |
C5—N2 | 1.326 (3) | C1A—H1AB | 0.9600 |
C6—H6 | 0.9300 | C1A—H1AC | 0.9600 |
C6—C7 | 1.377 (3) | C1A—C1B | 1.5071 |
C7—H7 | 0.9300 | C1B—C1C | 1.4021 |
C8—C9 | 1.390 (2) | C1B—C1G | 1.4020 |
C8—C13 | 1.391 (2) | C1C—H1C | 0.9300 |
C9—H9 | 0.9300 | C1C—C1D | 1.3962 |
C9—C10 | 1.370 (3) | C1D—H1D | 0.9300 |
C10—H10 | 0.9300 | C1D—C1E | 1.3965 |
C10—C11 | 1.372 (3) | C1E—H1E | 0.9300 |
C11—C12 | 1.357 (3) | C1E—C1F | 1.3964 |
C11—F1 | 1.364 (2) | C1F—H1F | 0.9300 |
C12—H12 | 0.9300 | C1F—C1G | 1.3964 |
C12—C13 | 1.381 (3) | C1G—H1G | 0.9300 |
C13—H13 | 0.9300 | ||
C8—C1—H1 | 106.4 | C15—C14—C19 | 119.51 (17) |
C8—C1—S1 | 112.28 (11) | C15—C14—N1 | 120.08 (17) |
N1—C1—H1 | 106.4 | C19—C14—N1 | 120.32 (16) |
N1—C1—C8 | 114.11 (13) | C14—C15—H15 | 120.0 |
N1—C1—S1 | 110.74 (12) | C14—C15—C16 | 119.9 (2) |
S1—C1—H1 | 106.4 | C16—C15—H15 | 120.0 |
N1—C2—C3 | 117.14 (14) | C15—C16—H16 | 119.7 |
O1—C2—C3 | 120.75 (15) | C17—C16—C15 | 120.6 (2) |
O1—C2—N1 | 122.10 (16) | C17—C16—H16 | 119.7 |
C4—C3—C2 | 123.80 (15) | C16—C17—H17 | 120.2 |
C7—C3—C2 | 118.96 (15) | C18—C17—C16 | 119.6 (2) |
C7—C3—C4 | 116.90 (16) | C18—C17—H17 | 120.2 |
C3—C4—S1 | 121.16 (13) | C17—C18—H18 | 119.8 |
N2—C4—C3 | 123.87 (17) | C17—C18—C19 | 120.4 (2) |
N2—C4—S1 | 114.95 (14) | C19—C18—H18 | 119.8 |
C6—C5—H5 | 118.0 | C14—C19—C18 | 119.9 (2) |
N2—C5—H5 | 118.0 | C14—C19—H19 | 120.0 |
N2—C5—C6 | 123.96 (19) | C18—C19—H19 | 120.0 |
C5—C6—H6 | 120.8 | C2—N1—C1 | 121.21 (14) |
C5—C6—C7 | 118.49 (19) | C2—N1—C14 | 120.90 (14) |
C7—C6—H6 | 120.8 | C14—N1—C1 | 117.80 (13) |
C3—C7—H7 | 120.2 | C5—N2—C4 | 117.11 (18) |
C6—C7—C3 | 119.57 (18) | C4—S1—C1 | 96.13 (8) |
C6—C7—H7 | 120.2 | C1C—C1B—C1A | 120.9 |
C9—C8—C1 | 119.36 (15) | C1G—C1B—C1A | 121.0 |
C9—C8—C13 | 117.94 (17) | C1G—C1B—C1C | 118.1 |
C13—C8—C1 | 122.62 (15) | C1B—C1C—H1C | 119.4 |
C8—C9—H9 | 119.3 | C1D—C1C—C1B | 121.1 |
C10—C9—C8 | 121.41 (18) | C1D—C1C—H1C | 119.4 |
C10—C9—H9 | 119.3 | C1C—C1D—H1D | 119.9 |
C9—C10—H10 | 120.8 | C1C—C1D—C1E | 120.1 |
C9—C10—C11 | 118.47 (19) | C1E—C1D—H1D | 119.9 |
C11—C10—H10 | 120.8 | C1D—C1E—H1E | 120.3 |
C12—C11—C10 | 122.5 (2) | C1F—C1E—C1D | 119.4 |
C12—C11—F1 | 118.5 (2) | C1F—C1E—H1E | 120.3 |
F1—C11—C10 | 119.0 (2) | C1E—C1F—H1F | 119.9 |
C11—C12—H12 | 120.7 | C1E—C1F—C1G | 120.1 |
C11—C12—C13 | 118.65 (19) | C1G—C1F—H1F | 119.9 |
C13—C12—H12 | 120.7 | C1B—C1G—H1G | 119.5 |
C8—C13—H13 | 119.5 | C1F—C1G—C1B | 121.1 |
C12—C13—C8 | 121.02 (18) | C1F—C1G—H1G | 119.5 |
C12—C13—H13 | 119.5 | ||
C1—C8—C9—C10 | −178.56 (17) | C19—C14—C15—C16 | 0.0 (3) |
C1—C8—C13—C12 | 178.16 (17) | C19—C14—N1—C1 | 51.1 (2) |
C2—C3—C4—N2 | 170.57 (18) | C19—C14—N1—C2 | −125.4 (2) |
C2—C3—C4—S1 | −7.9 (2) | F1—C11—C12—C13 | 178.40 (18) |
C2—C3—C7—C6 | −173.19 (17) | N1—C1—C8—C9 | −178.73 (15) |
C3—C2—N1—C1 | 14.2 (2) | N1—C1—C8—C13 | 4.6 (2) |
C3—C2—N1—C14 | −169.48 (15) | N1—C1—S1—C4 | 55.64 (13) |
C3—C4—N2—C5 | 2.1 (3) | N1—C2—C3—C4 | 21.2 (3) |
C3—C4—S1—C1 | −27.46 (16) | N1—C2—C3—C7 | −165.76 (16) |
C4—C3—C7—C6 | 0.4 (2) | N1—C14—C15—C16 | 176.57 (17) |
C5—C6—C7—C3 | 2.2 (3) | N1—C14—C19—C18 | −175.56 (19) |
C6—C5—N2—C4 | 0.8 (3) | N2—C4—S1—C1 | 153.98 (15) |
C7—C3—C4—N2 | −2.6 (3) | N2—C5—C6—C7 | −3.0 (3) |
C7—C3—C4—S1 | 178.93 (13) | O1—C2—C3—C4 | −157.79 (18) |
C8—C1—N1—C2 | 72.3 (2) | O1—C2—C3—C7 | 15.3 (3) |
C8—C1—N1—C14 | −104.19 (17) | O1—C2—N1—C1 | −166.91 (17) |
C8—C1—S1—C4 | −73.21 (12) | O1—C2—N1—C14 | 9.4 (3) |
C8—C9—C10—C11 | 0.3 (3) | S1—C1—C8—C9 | −51.67 (19) |
C9—C8—C13—C12 | 1.5 (3) | S1—C1—C8—C13 | 131.69 (15) |
C9—C10—C11—C12 | 1.6 (3) | S1—C1—N1—C2 | −55.58 (19) |
C9—C10—C11—F1 | −178.67 (19) | S1—C1—N1—C14 | 127.96 (14) |
C10—C11—C12—C13 | −1.8 (3) | S1—C4—N2—C5 | −179.41 (16) |
C11—C12—C13—C8 | 0.3 (3) | C1A—C1B—C1C—C1D | −178.5 |
C13—C8—C9—C10 | −1.8 (3) | C1A—C1B—C1G—C1F | 178.5 |
C14—C15—C16—C17 | −1.1 (3) | C1B—C1C—C1D—C1E | −0.1 |
C15—C14—C19—C18 | 1.0 (3) | C1C—C1B—C1G—C1F | −0.3 |
C15—C14—N1—C1 | −125.51 (18) | C1C—C1D—C1E—C1F | −0.1 |
C15—C14—N1—C2 | 58.0 (2) | C1D—C1E—C1F—C1G | 0.1 |
C15—C16—C17—C18 | 1.1 (3) | C1E—C1F—C1G—C1B | 0.1 |
C16—C17—C18—C19 | −0.1 (3) | C1G—C1B—C1C—C1D | 0.3 |
C17—C18—C19—C14 | −1.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.93 | 2.53 | 3.321 (2) | 143 |
C9—H9···N2ii | 0.93 | 2.58 | 3.398 (2) | 147 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, y−1/2, −z+3/2. |
4C19H13N3O3S·C3H8O·0.25H2O | Z = 2 |
Mr = 1518.13 | F(000) = 1577 |
Triclinic, P1 | Dx = 1.412 Mg m−3 |
a = 12.5451 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.9804 (17) Å | Cell parameters from 4843 reflections |
c = 19.434 (2) Å | θ = 2.4–28.2° |
α = 86.671 (2)° | µ = 0.21 mm−1 |
β = 72.369 (2)° | T = 298 K |
γ = 74.167 (2)° | Plate, colorless |
V = 3570.8 (6) Å3 | 0.19 × 0.18 × 0.03 mm |
Bruker CCD area detector diffractometer | 7969 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.039 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 28.4°, θmin = 1.3° |
Tmin = 0.230, Tmax = 0.9 | h = −16→16 |
30898 measured reflections | k = −20→20 |
16372 independent reflections | l = −25→25 |
Refinement on F2 | 30 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.002 |
16372 reflections | Δρmax = 0.28 e Å−3 |
997 parameters | Δρmin = −0.27 e Å−3 |
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 | Occ. (<1) | |
S1 | 0.29218 (6) | 0.03290 (5) | 0.18613 (4) | 0.0501 (2) | |
O1 | −0.04665 (16) | 0.18932 (12) | 0.17939 (10) | 0.0550 (5) | |
O2 | −0.0412 (3) | −0.27498 (17) | 0.35233 (15) | 0.0955 (8) | |
O3 | 0.0788 (3) | −0.29499 (16) | 0.41328 (14) | 0.0907 (8) | |
N1 | 0.06953 (17) | 0.12964 (14) | 0.24885 (11) | 0.0414 (5) | |
N2 | 0.2998 (2) | −0.01955 (15) | 0.05960 (13) | 0.0535 (6) | |
N3 | 0.0313 (3) | −0.25406 (18) | 0.37145 (15) | 0.0632 (7) | |
C1 | 0.1603 (2) | 0.05663 (17) | 0.26243 (14) | 0.0437 (7) | |
H1 | 0.181510 | 0.076401 | 0.302031 | 0.052* | |
C2 | 0.0381 (2) | 0.13447 (18) | 0.18683 (14) | 0.0426 (7) | |
C3 | 0.1134 (2) | 0.07162 (17) | 0.12647 (14) | 0.0415 (6) | |
C4 | 0.2284 (2) | 0.02717 (18) | 0.11932 (14) | 0.0440 (7) | |
C5 | 0.2559 (3) | −0.0235 (2) | 0.00611 (17) | 0.0597 (8) | |
H5 | 0.304997 | −0.054121 | −0.036014 | 0.072* | |
C6 | 0.1422 (3) | 0.0148 (2) | 0.00931 (16) | 0.0580 (8) | |
H6 | 0.114623 | 0.007952 | −0.028769 | 0.070* | |
C7 | 0.0699 (3) | 0.06374 (19) | 0.07008 (15) | 0.0502 (7) | |
H7 | −0.007133 | 0.091139 | 0.073294 | 0.060* | |
C8 | 0.0037 (2) | 0.19178 (19) | 0.30682 (15) | 0.0459 (7) | |
C9 | −0.0185 (2) | 0.28007 (19) | 0.29480 (17) | 0.0504 (7) | |
H9 | 0.008459 | 0.299760 | 0.248466 | 0.060* | |
C10 | −0.0806 (3) | 0.3390 (2) | 0.3512 (2) | 0.0633 (9) | |
H10 | −0.096270 | 0.398356 | 0.342596 | 0.076* | |
C11 | −0.1193 (3) | 0.3108 (3) | 0.4201 (2) | 0.0761 (11) | |
H11 | −0.161026 | 0.350794 | 0.458010 | 0.091* | |
C12 | −0.0963 (3) | 0.2229 (3) | 0.43276 (18) | 0.0784 (11) | |
H12 | −0.121912 | 0.203669 | 0.479409 | 0.094* | |
C13 | −0.0352 (3) | 0.1633 (2) | 0.37638 (16) | 0.0617 (9) | |
H13 | −0.020190 | 0.104029 | 0.385098 | 0.074* | |
C14 | 0.1239 (2) | −0.02529 (17) | 0.28802 (14) | 0.0412 (6) | |
C15 | 0.1940 (2) | −0.08729 (19) | 0.32026 (15) | 0.0518 (8) | |
H15 | 0.262207 | −0.077937 | 0.323669 | 0.062* | |
C16 | 0.1648 (3) | −0.16179 (19) | 0.34711 (15) | 0.0532 (8) | |
H16 | 0.212076 | −0.202681 | 0.368797 | 0.064* | |
C17 | 0.0643 (3) | −0.17473 (19) | 0.34131 (14) | 0.0479 (7) | |
C18 | −0.0068 (3) | −0.1158 (2) | 0.30966 (15) | 0.0532 (8) | |
H18 | −0.074127 | −0.126398 | 0.305862 | 0.064* | |
C19 | 0.0226 (2) | −0.04033 (19) | 0.28338 (15) | 0.0491 (7) | |
H19 | −0.025836 | 0.000607 | 0.262464 | 0.059* | |
S2 | 0.19473 (6) | 0.08666 (5) | 0.80114 (5) | 0.0613 (2) | |
O4 | 0.56806 (17) | −0.00558 (13) | 0.70493 (10) | 0.0574 (5) | |
O5 | 0.2168 (3) | 0.25409 (17) | 1.12494 (13) | 0.0845 (7) | |
O6 | 0.4024 (3) | 0.20792 (19) | 1.09163 (13) | 0.0952 (8) | |
N4 | 0.4121 (2) | 0.10919 (15) | 0.74362 (12) | 0.0500 (6) | |
N5 | 0.2221 (2) | −0.07471 (19) | 0.83891 (14) | 0.0596 (7) | |
N6 | 0.3093 (3) | 0.22173 (18) | 1.08058 (15) | 0.0633 (7) | |
C20 | 0.3005 (2) | 0.14686 (18) | 0.79718 (15) | 0.0498 (7) | |
H20 | 0.269897 | 0.204631 | 0.779922 | 0.060* | |
C21 | 0.4679 (2) | 0.02283 (19) | 0.74233 (15) | 0.0460 (7) | |
C22 | 0.4024 (2) | −0.03636 (18) | 0.78632 (14) | 0.0436 (7) | |
C23 | 0.2810 (2) | −0.0166 (2) | 0.81035 (15) | 0.0496 (7) | |
C24 | 0.2841 (3) | −0.1547 (2) | 0.84727 (17) | 0.0632 (9) | |
H24 | 0.244423 | −0.196368 | 0.865752 | 0.076* | |
C25 | 0.4028 (3) | −0.1794 (2) | 0.83030 (17) | 0.0593 (8) | |
H25 | 0.441822 | −0.234882 | 0.840296 | 0.071* | |
C26 | 0.4626 (3) | −0.12010 (19) | 0.79817 (16) | 0.0518 (7) | |
H26 | 0.543281 | −0.135961 | 0.784345 | 0.062* | |
C27 | 0.4675 (2) | 0.16600 (19) | 0.69490 (16) | 0.0511 (7) | |
C28 | 0.4947 (3) | 0.1525 (2) | 0.62135 (17) | 0.0714 (10) | |
H28 | 0.477424 | 0.106687 | 0.603497 | 0.086* | |
C29 | 0.5478 (3) | 0.2075 (3) | 0.5746 (2) | 0.0849 (12) | |
H29 | 0.567327 | 0.198167 | 0.525004 | 0.102* | |
C30 | 0.5721 (3) | 0.2757 (3) | 0.6005 (2) | 0.0811 (11) | |
H30 | 0.607450 | 0.312659 | 0.568546 | 0.097* | |
C31 | 0.5445 (3) | 0.2897 (2) | 0.6732 (2) | 0.0740 (10) | |
H31 | 0.560919 | 0.336212 | 0.690674 | 0.089* | |
C32 | 0.4921 (3) | 0.2349 (2) | 0.72099 (18) | 0.0605 (8) | |
H32 | 0.473560 | 0.244328 | 0.770509 | 0.073* | |
C33 | 0.3067 (2) | 0.16168 (17) | 0.87210 (15) | 0.0433 (7) | |
C34 | 0.4083 (2) | 0.13472 (18) | 0.89128 (16) | 0.0507 (7) | |
H34 | 0.476271 | 0.103994 | 0.857772 | 0.061* | |
C35 | 0.4099 (3) | 0.15283 (19) | 0.95934 (16) | 0.0544 (8) | |
H35 | 0.478404 | 0.135045 | 0.971940 | 0.065* | |
C36 | 0.3084 (3) | 0.19765 (18) | 1.00816 (15) | 0.0479 (7) | |
C37 | 0.2059 (3) | 0.22324 (18) | 0.99185 (16) | 0.0518 (7) | |
H37 | 0.137821 | 0.252247 | 1.026239 | 0.062* | |
C38 | 0.2052 (2) | 0.20535 (18) | 0.92384 (16) | 0.0493 (7) | |
H38 | 0.135942 | 0.222643 | 0.912096 | 0.059* | |
S3 | 0.48325 (6) | 0.54203 (5) | 0.79720 (5) | 0.0604 (2) | |
O7 | 0.13744 (16) | 0.53956 (13) | 0.79718 (11) | 0.0584 (5) | |
O8 | 0.2856 (3) | 0.96125 (17) | 0.64375 (14) | 0.0961 (9) | |
O9 | 0.4647 (3) | 0.92989 (18) | 0.58597 (18) | 0.1164 (11) | |
N7 | 0.32514 (18) | 0.52725 (15) | 0.73153 (12) | 0.0476 (6) | |
N8 | 0.3661 (2) | 0.61800 (17) | 0.92278 (15) | 0.0650 (7) | |
N9 | 0.3801 (3) | 0.9097 (2) | 0.62374 (15) | 0.0657 (7) | |
C39 | 0.4283 (2) | 0.55876 (18) | 0.71966 (16) | 0.0494 (7) | |
H39 | 0.488822 | 0.522418 | 0.680202 | 0.059* | |
C40 | 0.2314 (2) | 0.55268 (18) | 0.79167 (16) | 0.0479 (7) | |
C41 | 0.2460 (2) | 0.59634 (18) | 0.85278 (15) | 0.0467 (7) | |
C42 | 0.3535 (2) | 0.59082 (18) | 0.86259 (16) | 0.0518 (7) | |
C43 | 0.2685 (4) | 0.6551 (2) | 0.97386 (19) | 0.0726 (10) | |
H43 | 0.274854 | 0.673113 | 1.016759 | 0.087* | |
C44 | 0.1595 (3) | 0.6684 (2) | 0.96741 (18) | 0.0682 (9) | |
H44 | 0.094536 | 0.697668 | 1.003856 | 0.082* | |
C45 | 0.1474 (3) | 0.63801 (19) | 0.90639 (16) | 0.0559 (8) | |
H45 | 0.074191 | 0.645318 | 0.901185 | 0.067* | |
C46 | 0.3174 (2) | 0.4816 (2) | 0.67217 (17) | 0.0519 (8) | |
C47 | 0.3583 (3) | 0.5075 (2) | 0.60260 (19) | 0.0687 (9) | |
H47 | 0.390137 | 0.554651 | 0.593770 | 0.082* | |
C48 | 0.3516 (3) | 0.4627 (3) | 0.5459 (2) | 0.0886 (12) | |
H48 | 0.380530 | 0.479097 | 0.498715 | 0.106* | |
C49 | 0.3020 (3) | 0.3938 (3) | 0.5591 (3) | 0.0927 (13) | |
H49 | 0.295729 | 0.364785 | 0.521042 | 0.111* | |
C50 | 0.2623 (3) | 0.3685 (3) | 0.6286 (3) | 0.0845 (12) | |
H50 | 0.229480 | 0.321849 | 0.637564 | 0.101* | |
C51 | 0.2705 (3) | 0.4115 (2) | 0.6853 (2) | 0.0646 (9) | |
H51 | 0.244613 | 0.393393 | 0.732351 | 0.078* | |
C52 | 0.4134 (2) | 0.65204 (18) | 0.69454 (14) | 0.0442 (7) | |
C53 | 0.3052 (2) | 0.71039 (19) | 0.70482 (15) | 0.0499 (7) | |
H53 | 0.238603 | 0.692619 | 0.727595 | 0.060* | |
C54 | 0.2952 (2) | 0.79473 (19) | 0.68155 (15) | 0.0509 (7) | |
H54 | 0.222522 | 0.834073 | 0.689347 | 0.061* | |
C55 | 0.3930 (3) | 0.81948 (19) | 0.64715 (15) | 0.0492 (7) | |
C56 | 0.5027 (3) | 0.7632 (2) | 0.63555 (16) | 0.0572 (8) | |
H56 | 0.568763 | 0.781216 | 0.612004 | 0.069* | |
C57 | 0.5112 (2) | 0.6801 (2) | 0.65971 (16) | 0.0554 (8) | |
H57 | 0.584312 | 0.641513 | 0.652624 | 0.066* | |
S4 | −0.00824 (6) | 0.62257 (5) | 0.19021 (5) | 0.0601 (2) | |
O10 | 0.27502 (19) | 0.58431 (14) | 0.28290 (11) | 0.0660 (6) | |
O11 | 0.4765 (3) | 0.3508 (2) | −0.09779 (15) | 0.1215 (11) | |
O12 | 0.3228 (3) | 0.37649 (17) | −0.13080 (14) | 0.0992 (9) | |
N10 | 0.1560 (2) | 0.52364 (15) | 0.24786 (12) | 0.0486 (6) | |
N11 | 0.0602 (2) | 0.76000 (18) | 0.14094 (15) | 0.0687 (8) | |
N12 | 0.3728 (3) | 0.37844 (19) | −0.08640 (17) | 0.0780 (9) | |
C58 | 0.0938 (2) | 0.51872 (18) | 0.19627 (15) | 0.0481 (7) | |
H58 | 0.047299 | 0.477654 | 0.215668 | 0.058* | |
C59 | 0.2114 (3) | 0.5869 (2) | 0.24570 (16) | 0.0506 (7) | |
C60 | 0.1878 (2) | 0.66125 (19) | 0.19797 (15) | 0.0479 (7) | |
C61 | 0.0896 (2) | 0.68606 (19) | 0.17441 (16) | 0.0537 (8) | |
C62 | 0.1314 (4) | 0.8109 (2) | 0.1284 (2) | 0.0767 (10) | |
H62 | 0.110636 | 0.863692 | 0.106534 | 0.092* | |
C63 | 0.2332 (3) | 0.7909 (2) | 0.14539 (18) | 0.0709 (10) | |
H63 | 0.282649 | 0.826976 | 0.132484 | 0.085* | |
C64 | 0.2609 (3) | 0.7155 (2) | 0.18231 (16) | 0.0585 (8) | |
H64 | 0.327943 | 0.701254 | 0.196506 | 0.070* | |
C65 | 0.1627 (3) | 0.4563 (2) | 0.30032 (17) | 0.0534 (8) | |
C66 | 0.1160 (3) | 0.4788 (2) | 0.37276 (18) | 0.0774 (10) | |
H66 | 0.082455 | 0.536872 | 0.387554 | 0.093* | |
C67 | 0.1197 (4) | 0.4145 (3) | 0.4230 (2) | 0.0930 (12) | |
H67 | 0.089317 | 0.429214 | 0.472005 | 0.112* | |
C68 | 0.1681 (3) | 0.3289 (3) | 0.4009 (2) | 0.0830 (12) | |
H68 | 0.168995 | 0.285587 | 0.435030 | 0.100* | |
C69 | 0.2145 (3) | 0.3072 (2) | 0.3297 (2) | 0.0749 (10) | |
H69 | 0.248019 | 0.249089 | 0.315232 | 0.090* | |
C70 | 0.2125 (3) | 0.3707 (2) | 0.27805 (18) | 0.0606 (8) | |
H70 | 0.244378 | 0.355613 | 0.229149 | 0.073* | |
C71 | 0.1711 (2) | 0.48386 (17) | 0.12155 (14) | 0.0425 (7) | |
C72 | 0.2909 (2) | 0.46199 (19) | 0.10238 (17) | 0.0545 (8) | |
H72 | 0.327051 | 0.470172 | 0.135774 | 0.065* | |
C73 | 0.3576 (3) | 0.4282 (2) | 0.03438 (18) | 0.0608 (8) | |
H73 | 0.438223 | 0.413308 | 0.021859 | 0.073* | |
C74 | 0.3033 (3) | 0.41698 (19) | −0.01417 (16) | 0.0561 (8) | |
C75 | 0.1842 (3) | 0.43826 (19) | 0.00298 (17) | 0.0591 (8) | |
H75 | 0.148616 | 0.430409 | −0.030836 | 0.071* | |
C76 | 0.1192 (3) | 0.47116 (18) | 0.07068 (16) | 0.0510 (7) | |
H76 | 0.038687 | 0.485333 | 0.082884 | 0.061* | |
O13 | 0.2504 (2) | 0.10492 (18) | 0.40343 (12) | 0.1046 (9) | |
H13A | 0.303804 | 0.061308 | 0.387928 | 0.157* | 0.58 (2) |
H13B | 0.302801 | 0.076905 | 0.369810 | 0.157* | 0.42 (2) |
C77 | 0.1668 (5) | 0.0177 (4) | 0.4961 (3) | 0.1325 (18) | |
H77A | 0.109954 | 0.014164 | 0.473447 | 0.199* | 0.58 (2) |
H77B | 0.135100 | 0.015458 | 0.547577 | 0.199* | 0.58 (2) |
H77C | 0.234562 | −0.030317 | 0.479476 | 0.199* | 0.58 (2) |
H77D | 0.092788 | 0.060158 | 0.507324 | 0.199* | 0.42 (2) |
H77E | 0.171687 | −0.017491 | 0.537416 | 0.199* | 0.42 (2) |
H77F | 0.175255 | −0.018666 | 0.456135 | 0.199* | 0.42 (2) |
C79 | 0.2605 (4) | 0.1265 (3) | 0.5221 (2) | 0.1003 (13) | |
H79A | 0.338032 | 0.089162 | 0.511710 | 0.150* | 0.58 (2) |
H79B | 0.220463 | 0.124443 | 0.572520 | 0.150* | 0.58 (2) |
H79C | 0.263384 | 0.185085 | 0.509982 | 0.150* | 0.58 (2) |
H79D | 0.324091 | 0.151322 | 0.500445 | 0.150* | 0.42 (2) |
H79E | 0.267326 | 0.101210 | 0.567084 | 0.150* | 0.42 (2) |
H79F | 0.188591 | 0.171108 | 0.530563 | 0.150* | 0.42 (2) |
O14 | 0.3199 (9) | 0.5360 (8) | 0.4020 (6) | 0.099 (3) | 0.25 |
H14A | 0.283502 | 0.500854 | 0.426031 | 0.148* | 0.25 |
H14B | 0.277331 | 0.587867 | 0.411647 | 0.148* | 0.25 |
C78A | 0.1974 (14) | 0.0965 (10) | 0.4784 (4) | 0.077 (3) | 0.58 (2) |
H78A | 0.122575 | 0.140645 | 0.488887 | 0.092* | 0.58 (2) |
C78B | 0.2625 (18) | 0.0633 (10) | 0.4765 (6) | 0.079 (4) | 0.42 (2) |
H78B | 0.337343 | 0.019326 | 0.466878 | 0.095* | 0.42 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0371 (4) | 0.0596 (5) | 0.0533 (5) | −0.0121 (3) | −0.0145 (3) | 0.0032 (4) |
O1 | 0.0471 (11) | 0.0562 (13) | 0.0612 (13) | −0.0020 (10) | −0.0250 (10) | −0.0045 (10) |
O2 | 0.118 (2) | 0.092 (2) | 0.104 (2) | −0.0665 (18) | −0.0394 (18) | 0.0080 (16) |
O3 | 0.134 (2) | 0.0693 (17) | 0.0782 (18) | −0.0354 (16) | −0.0412 (17) | 0.0227 (14) |
N1 | 0.0405 (12) | 0.0433 (13) | 0.0402 (13) | −0.0069 (10) | −0.0150 (10) | −0.0031 (11) |
N2 | 0.0485 (14) | 0.0568 (16) | 0.0490 (15) | −0.0128 (12) | −0.0063 (12) | −0.0020 (13) |
N3 | 0.085 (2) | 0.0573 (18) | 0.0483 (17) | −0.0295 (16) | −0.0111 (15) | −0.0055 (14) |
C1 | 0.0409 (15) | 0.0486 (17) | 0.0448 (16) | −0.0104 (13) | −0.0186 (13) | 0.0010 (13) |
C2 | 0.0393 (15) | 0.0488 (17) | 0.0439 (17) | −0.0152 (13) | −0.0152 (13) | 0.0003 (14) |
C3 | 0.0432 (15) | 0.0438 (16) | 0.0396 (16) | −0.0157 (13) | −0.0117 (13) | 0.0010 (13) |
C4 | 0.0409 (15) | 0.0452 (17) | 0.0428 (16) | −0.0136 (13) | −0.0063 (13) | 0.0031 (14) |
C5 | 0.062 (2) | 0.067 (2) | 0.0471 (19) | −0.0188 (17) | −0.0077 (16) | −0.0118 (16) |
C6 | 0.065 (2) | 0.070 (2) | 0.0433 (18) | −0.0245 (17) | −0.0152 (16) | −0.0056 (16) |
C7 | 0.0505 (17) | 0.0538 (18) | 0.0510 (18) | −0.0192 (14) | −0.0174 (15) | 0.0014 (15) |
C8 | 0.0388 (15) | 0.0519 (19) | 0.0466 (18) | −0.0087 (13) | −0.0141 (13) | −0.0063 (15) |
C9 | 0.0445 (16) | 0.0509 (19) | 0.0591 (19) | −0.0116 (14) | −0.0201 (15) | −0.0054 (16) |
C10 | 0.0559 (19) | 0.056 (2) | 0.076 (2) | −0.0039 (16) | −0.0243 (18) | −0.0153 (19) |
C11 | 0.065 (2) | 0.081 (3) | 0.072 (3) | 0.006 (2) | −0.022 (2) | −0.032 (2) |
C12 | 0.082 (3) | 0.089 (3) | 0.048 (2) | −0.001 (2) | −0.0141 (18) | −0.012 (2) |
C13 | 0.071 (2) | 0.058 (2) | 0.050 (2) | −0.0072 (17) | −0.0170 (17) | −0.0056 (17) |
C14 | 0.0417 (15) | 0.0468 (17) | 0.0373 (15) | −0.0126 (13) | −0.0136 (12) | −0.0019 (13) |
C15 | 0.0451 (16) | 0.058 (2) | 0.0575 (19) | −0.0149 (14) | −0.0222 (14) | 0.0071 (16) |
C16 | 0.0523 (18) | 0.0507 (19) | 0.0534 (19) | −0.0086 (15) | −0.0171 (15) | 0.0070 (15) |
C17 | 0.0583 (18) | 0.0483 (18) | 0.0366 (16) | −0.0187 (15) | −0.0089 (14) | −0.0022 (14) |
C18 | 0.0544 (18) | 0.067 (2) | 0.0487 (18) | −0.0285 (16) | −0.0204 (15) | 0.0026 (16) |
C19 | 0.0484 (17) | 0.0560 (19) | 0.0491 (17) | −0.0175 (14) | −0.0215 (14) | 0.0068 (15) |
S2 | 0.0445 (4) | 0.0671 (5) | 0.0745 (6) | −0.0002 (4) | −0.0304 (4) | −0.0187 (4) |
O4 | 0.0454 (12) | 0.0598 (13) | 0.0554 (12) | −0.0021 (10) | −0.0076 (10) | −0.0059 (10) |
O5 | 0.109 (2) | 0.0879 (19) | 0.0523 (15) | −0.0279 (16) | −0.0143 (15) | −0.0117 (13) |
O6 | 0.105 (2) | 0.126 (2) | 0.0771 (18) | −0.0361 (18) | −0.0556 (16) | 0.0061 (16) |
N4 | 0.0520 (14) | 0.0469 (15) | 0.0442 (14) | −0.0031 (12) | −0.0126 (12) | −0.0044 (12) |
N5 | 0.0523 (15) | 0.0680 (19) | 0.0641 (17) | −0.0232 (15) | −0.0161 (13) | −0.0142 (15) |
N6 | 0.090 (2) | 0.0581 (18) | 0.0512 (18) | −0.0301 (17) | −0.0269 (18) | 0.0066 (14) |
C20 | 0.0483 (17) | 0.0461 (17) | 0.0508 (18) | −0.0007 (13) | −0.0182 (14) | −0.0052 (14) |
C21 | 0.0444 (16) | 0.0495 (18) | 0.0423 (17) | −0.0029 (14) | −0.0172 (14) | −0.0098 (14) |
C22 | 0.0418 (15) | 0.0507 (18) | 0.0411 (16) | −0.0100 (14) | −0.0168 (13) | −0.0082 (14) |
C23 | 0.0458 (17) | 0.059 (2) | 0.0476 (18) | −0.0087 (15) | −0.0201 (14) | −0.0175 (15) |
C24 | 0.072 (2) | 0.064 (2) | 0.062 (2) | −0.0297 (19) | −0.0208 (18) | −0.0054 (18) |
C25 | 0.067 (2) | 0.055 (2) | 0.064 (2) | −0.0179 (17) | −0.0284 (17) | 0.0002 (17) |
C26 | 0.0504 (17) | 0.0536 (19) | 0.0540 (18) | −0.0098 (15) | −0.0217 (15) | −0.0063 (15) |
C27 | 0.0533 (17) | 0.0461 (18) | 0.0500 (19) | −0.0055 (14) | −0.0169 (15) | 0.0009 (15) |
C28 | 0.093 (3) | 0.071 (2) | 0.048 (2) | −0.016 (2) | −0.0235 (19) | 0.0020 (18) |
C29 | 0.102 (3) | 0.089 (3) | 0.055 (2) | −0.022 (2) | −0.018 (2) | 0.014 (2) |
C30 | 0.072 (2) | 0.074 (3) | 0.085 (3) | −0.013 (2) | −0.017 (2) | 0.027 (2) |
C31 | 0.066 (2) | 0.058 (2) | 0.099 (3) | −0.0140 (18) | −0.030 (2) | 0.008 (2) |
C32 | 0.066 (2) | 0.054 (2) | 0.060 (2) | −0.0117 (17) | −0.0209 (17) | 0.0003 (17) |
C33 | 0.0431 (15) | 0.0356 (15) | 0.0492 (17) | −0.0056 (12) | −0.0149 (13) | −0.0013 (13) |
C34 | 0.0441 (16) | 0.0520 (18) | 0.0513 (19) | −0.0027 (14) | −0.0152 (14) | −0.0060 (15) |
C35 | 0.0551 (19) | 0.0558 (19) | 0.058 (2) | −0.0120 (15) | −0.0289 (16) | 0.0057 (16) |
C36 | 0.0624 (19) | 0.0414 (17) | 0.0448 (17) | −0.0185 (15) | −0.0194 (15) | 0.0020 (14) |
C37 | 0.0518 (18) | 0.0465 (18) | 0.0534 (19) | −0.0116 (14) | −0.0101 (15) | −0.0068 (15) |
C38 | 0.0413 (16) | 0.0491 (18) | 0.0584 (19) | −0.0082 (13) | −0.0181 (14) | −0.0063 (15) |
S3 | 0.0437 (4) | 0.0639 (5) | 0.0757 (6) | −0.0115 (4) | −0.0240 (4) | 0.0039 (4) |
O7 | 0.0379 (11) | 0.0709 (14) | 0.0660 (14) | −0.0219 (10) | −0.0072 (10) | −0.0050 (11) |
O8 | 0.103 (2) | 0.0682 (17) | 0.097 (2) | −0.0031 (16) | −0.0212 (17) | 0.0161 (15) |
O9 | 0.091 (2) | 0.090 (2) | 0.165 (3) | −0.0441 (17) | −0.024 (2) | 0.052 (2) |
N7 | 0.0384 (13) | 0.0525 (15) | 0.0515 (15) | −0.0166 (11) | −0.0075 (11) | −0.0059 (12) |
N8 | 0.079 (2) | 0.0635 (18) | 0.0610 (18) | −0.0200 (15) | −0.0319 (16) | 0.0020 (15) |
N9 | 0.079 (2) | 0.066 (2) | 0.0620 (18) | −0.0295 (18) | −0.0288 (17) | 0.0136 (16) |
C39 | 0.0333 (14) | 0.0513 (18) | 0.0602 (19) | −0.0134 (13) | −0.0061 (13) | −0.0056 (15) |
C40 | 0.0429 (17) | 0.0461 (17) | 0.0529 (18) | −0.0137 (14) | −0.0108 (14) | 0.0042 (14) |
C41 | 0.0462 (16) | 0.0459 (17) | 0.0497 (18) | −0.0166 (14) | −0.0139 (14) | 0.0055 (14) |
C42 | 0.0556 (18) | 0.0455 (18) | 0.057 (2) | −0.0149 (14) | −0.0217 (15) | 0.0101 (15) |
C43 | 0.096 (3) | 0.068 (2) | 0.058 (2) | −0.020 (2) | −0.028 (2) | −0.0015 (19) |
C44 | 0.076 (2) | 0.060 (2) | 0.058 (2) | −0.0113 (18) | −0.0096 (18) | −0.0072 (17) |
C45 | 0.0539 (18) | 0.0546 (19) | 0.054 (2) | −0.0118 (15) | −0.0107 (16) | 0.0016 (16) |
C46 | 0.0377 (15) | 0.0528 (19) | 0.062 (2) | −0.0078 (14) | −0.0131 (15) | −0.0095 (16) |
C47 | 0.069 (2) | 0.070 (2) | 0.061 (2) | −0.0176 (18) | −0.0110 (18) | −0.0083 (19) |
C48 | 0.090 (3) | 0.104 (3) | 0.064 (3) | −0.013 (3) | −0.018 (2) | −0.020 (2) |
C49 | 0.081 (3) | 0.111 (4) | 0.095 (3) | −0.018 (3) | −0.038 (3) | −0.042 (3) |
C50 | 0.066 (2) | 0.087 (3) | 0.109 (3) | −0.031 (2) | −0.022 (2) | −0.033 (3) |
C51 | 0.0478 (18) | 0.067 (2) | 0.082 (2) | −0.0231 (16) | −0.0138 (17) | −0.0099 (19) |
C52 | 0.0354 (15) | 0.0520 (18) | 0.0475 (17) | −0.0168 (13) | −0.0102 (13) | −0.0036 (14) |
C53 | 0.0376 (15) | 0.057 (2) | 0.0585 (19) | −0.0199 (14) | −0.0130 (14) | 0.0012 (16) |
C54 | 0.0429 (16) | 0.054 (2) | 0.0564 (19) | −0.0126 (14) | −0.0167 (14) | 0.0034 (15) |
C55 | 0.0572 (19) | 0.0515 (19) | 0.0449 (17) | −0.0194 (15) | −0.0195 (15) | 0.0027 (14) |
C56 | 0.0469 (18) | 0.064 (2) | 0.064 (2) | −0.0277 (16) | −0.0099 (15) | 0.0058 (17) |
C57 | 0.0362 (15) | 0.057 (2) | 0.071 (2) | −0.0153 (14) | −0.0106 (15) | 0.0020 (17) |
S4 | 0.0411 (4) | 0.0577 (5) | 0.0746 (6) | −0.0084 (4) | −0.0097 (4) | −0.0085 (4) |
O10 | 0.0748 (15) | 0.0827 (16) | 0.0578 (13) | −0.0422 (13) | −0.0262 (12) | 0.0025 (12) |
O11 | 0.095 (2) | 0.132 (3) | 0.086 (2) | 0.011 (2) | 0.0140 (18) | −0.0144 (18) |
O12 | 0.151 (3) | 0.0831 (19) | 0.0562 (16) | −0.0310 (18) | −0.0192 (18) | −0.0104 (14) |
N10 | 0.0553 (14) | 0.0547 (15) | 0.0427 (14) | −0.0257 (12) | −0.0150 (12) | 0.0023 (12) |
N11 | 0.0681 (18) | 0.0474 (17) | 0.079 (2) | −0.0047 (15) | −0.0136 (15) | −0.0069 (15) |
N12 | 0.099 (3) | 0.0574 (19) | 0.057 (2) | −0.0146 (18) | 0.000 (2) | 0.0009 (16) |
C58 | 0.0467 (16) | 0.0489 (18) | 0.0529 (18) | −0.0194 (14) | −0.0150 (14) | 0.0003 (14) |
C59 | 0.0500 (17) | 0.057 (2) | 0.0453 (18) | −0.0219 (15) | −0.0071 (14) | −0.0076 (15) |
C60 | 0.0482 (17) | 0.0467 (18) | 0.0445 (17) | −0.0159 (14) | −0.0029 (14) | −0.0086 (14) |
C61 | 0.0481 (17) | 0.0453 (18) | 0.0540 (19) | −0.0038 (14) | −0.0010 (15) | −0.0123 (15) |
C62 | 0.089 (3) | 0.049 (2) | 0.079 (3) | −0.009 (2) | −0.014 (2) | 0.0016 (19) |
C63 | 0.085 (3) | 0.052 (2) | 0.067 (2) | −0.0310 (19) | 0.001 (2) | −0.0010 (18) |
C64 | 0.0565 (19) | 0.060 (2) | 0.0548 (19) | −0.0230 (16) | −0.0025 (15) | −0.0088 (17) |
C65 | 0.0562 (18) | 0.056 (2) | 0.053 (2) | −0.0225 (16) | −0.0169 (15) | 0.0050 (16) |
C66 | 0.107 (3) | 0.071 (2) | 0.050 (2) | −0.028 (2) | −0.013 (2) | 0.0068 (19) |
C67 | 0.119 (3) | 0.104 (4) | 0.054 (2) | −0.036 (3) | −0.020 (2) | 0.019 (2) |
C68 | 0.076 (3) | 0.098 (3) | 0.091 (3) | −0.039 (2) | −0.042 (2) | 0.042 (3) |
C69 | 0.060 (2) | 0.065 (2) | 0.111 (3) | −0.0186 (18) | −0.043 (2) | 0.021 (2) |
C70 | 0.0555 (19) | 0.063 (2) | 0.068 (2) | −0.0200 (16) | −0.0230 (16) | 0.0060 (19) |
C71 | 0.0457 (16) | 0.0379 (16) | 0.0438 (16) | −0.0113 (13) | −0.0130 (13) | 0.0001 (13) |
C72 | 0.0460 (17) | 0.059 (2) | 0.061 (2) | −0.0135 (15) | −0.0183 (15) | −0.0031 (16) |
C73 | 0.0456 (17) | 0.063 (2) | 0.062 (2) | −0.0090 (15) | −0.0032 (16) | −0.0036 (17) |
C74 | 0.073 (2) | 0.0427 (18) | 0.0426 (18) | −0.0097 (16) | −0.0075 (17) | 0.0001 (14) |
C75 | 0.080 (2) | 0.0490 (19) | 0.054 (2) | −0.0126 (17) | −0.0315 (18) | −0.0025 (16) |
C76 | 0.0500 (17) | 0.0489 (18) | 0.059 (2) | −0.0121 (14) | −0.0234 (16) | −0.0039 (15) |
O13 | 0.115 (2) | 0.112 (2) | 0.0486 (15) | 0.0127 (17) | −0.0069 (14) | −0.0010 (14) |
C77 | 0.176 (6) | 0.156 (5) | 0.090 (3) | −0.079 (4) | −0.044 (4) | 0.007 (3) |
C79 | 0.117 (4) | 0.116 (4) | 0.071 (3) | −0.037 (3) | −0.033 (3) | 0.024 (3) |
O14 | 0.079 (7) | 0.128 (9) | 0.085 (8) | −0.016 (7) | −0.032 (6) | 0.024 (7) |
C78A | 0.082 (7) | 0.096 (8) | 0.050 (4) | −0.024 (6) | −0.017 (5) | 0.000 (4) |
C78B | 0.074 (9) | 0.085 (8) | 0.049 (6) | 0.010 (7) | −0.003 (6) | 0.003 (5) |
S1—C1 | 1.821 (3) | C39—C52 | 1.521 (4) |
S1—C4 | 1.737 (3) | C40—C41 | 1.493 (4) |
O1—C2 | 1.221 (3) | C41—C42 | 1.397 (4) |
O2—N3 | 1.209 (3) | C41—C45 | 1.382 (4) |
O3—N3 | 1.209 (3) | C43—H43 | 0.9300 |
N1—C1 | 1.466 (3) | C43—C44 | 1.369 (5) |
N1—C2 | 1.369 (3) | C44—H44 | 0.9300 |
N1—C8 | 1.434 (3) | C44—C45 | 1.371 (4) |
N2—C4 | 1.346 (3) | C45—H45 | 0.9300 |
N2—C5 | 1.327 (4) | C46—C47 | 1.376 (4) |
N3—C17 | 1.475 (4) | C46—C51 | 1.378 (4) |
C1—H1 | 0.9800 | C47—H47 | 0.9300 |
C1—C14 | 1.511 (4) | C47—C48 | 1.383 (5) |
C2—C3 | 1.492 (4) | C48—H48 | 0.9300 |
C3—C4 | 1.392 (3) | C48—C49 | 1.382 (5) |
C3—C7 | 1.389 (4) | C49—H49 | 0.9300 |
C5—H5 | 0.9300 | C49—C50 | 1.369 (5) |
C5—C6 | 1.374 (4) | C50—H50 | 0.9300 |
C6—H6 | 0.9300 | C50—C51 | 1.376 (5) |
C6—C7 | 1.378 (4) | C51—H51 | 0.9300 |
C7—H7 | 0.9300 | C52—C53 | 1.385 (4) |
C8—C9 | 1.382 (4) | C52—C57 | 1.388 (4) |
C8—C13 | 1.387 (4) | C53—H53 | 0.9300 |
C9—H9 | 0.9300 | C53—C54 | 1.381 (4) |
C9—C10 | 1.378 (4) | C54—H54 | 0.9300 |
C10—H10 | 0.9300 | C54—C55 | 1.358 (4) |
C10—C11 | 1.374 (5) | C55—C56 | 1.384 (4) |
C11—H11 | 0.9300 | C56—H56 | 0.9300 |
C11—C12 | 1.377 (5) | C56—C57 | 1.369 (4) |
C12—H12 | 0.9300 | C57—H57 | 0.9300 |
C12—C13 | 1.382 (4) | S4—C58 | 1.821 (3) |
C13—H13 | 0.9300 | S4—C61 | 1.746 (3) |
C14—C15 | 1.390 (3) | O10—C59 | 1.220 (3) |
C14—C19 | 1.385 (4) | O11—N12 | 1.207 (4) |
C15—H15 | 0.9300 | O12—N12 | 1.217 (4) |
C15—C16 | 1.369 (4) | N10—C58 | 1.461 (3) |
C16—H16 | 0.9300 | N10—C59 | 1.367 (3) |
C16—C17 | 1.369 (4) | N10—C65 | 1.443 (4) |
C17—C18 | 1.366 (4) | N11—C61 | 1.332 (4) |
C18—H18 | 0.9300 | N11—C62 | 1.327 (4) |
C18—C19 | 1.382 (4) | N12—C74 | 1.475 (4) |
C19—H19 | 0.9300 | C58—H58 | 0.9800 |
S2—C20 | 1.821 (3) | C58—C71 | 1.518 (4) |
S2—C23 | 1.742 (3) | C59—C60 | 1.486 (4) |
O4—C21 | 1.219 (3) | C60—C61 | 1.392 (4) |
O5—N6 | 1.214 (3) | C60—C64 | 1.385 (4) |
O6—N6 | 1.211 (3) | C62—H62 | 0.9300 |
N4—C20 | 1.462 (3) | C62—C63 | 1.365 (5) |
N4—C21 | 1.364 (3) | C63—H63 | 0.9300 |
N4—C27 | 1.432 (4) | C63—C64 | 1.382 (4) |
N5—C23 | 1.335 (4) | C64—H64 | 0.9300 |
N5—C24 | 1.332 (4) | C65—C66 | 1.378 (4) |
N6—C36 | 1.484 (4) | C65—C70 | 1.373 (4) |
C20—H20 | 0.9800 | C66—H66 | 0.9300 |
C20—C33 | 1.517 (4) | C66—C67 | 1.377 (5) |
C21—C22 | 1.485 (4) | C67—H67 | 0.9300 |
C22—C23 | 1.400 (4) | C67—C68 | 1.372 (5) |
C22—C26 | 1.390 (4) | C68—H68 | 0.9300 |
C24—H24 | 0.9300 | C68—C69 | 1.354 (5) |
C24—C25 | 1.370 (4) | C69—H69 | 0.9300 |
C25—H25 | 0.9300 | C69—C70 | 1.385 (4) |
C25—C26 | 1.373 (4) | C70—H70 | 0.9300 |
C26—H26 | 0.9300 | C71—C72 | 1.382 (4) |
C27—C28 | 1.381 (4) | C71—C76 | 1.388 (4) |
C27—C32 | 1.382 (4) | C72—H72 | 0.9300 |
C28—H28 | 0.9300 | C72—C73 | 1.380 (4) |
C28—C29 | 1.380 (5) | C73—H73 | 0.9300 |
C29—H29 | 0.9300 | C73—C74 | 1.365 (4) |
C29—C30 | 1.368 (5) | C74—C75 | 1.375 (4) |
C30—H30 | 0.9300 | C75—H75 | 0.9300 |
C30—C31 | 1.366 (5) | C75—C76 | 1.367 (4) |
C31—H31 | 0.9300 | C76—H76 | 0.9300 |
C31—C32 | 1.382 (4) | O13—H13A | 0.8200 |
C32—H32 | 0.9300 | O13—H13B | 0.8200 |
C33—C34 | 1.385 (3) | O13—C78A | 1.422 (8) |
C33—C38 | 1.393 (4) | O13—C78B | 1.564 (14) |
C34—H34 | 0.9300 | C77—H77A | 0.9600 |
C34—C35 | 1.378 (4) | C77—H77B | 0.9600 |
C35—H35 | 0.9300 | C77—H77C | 0.9600 |
C35—C36 | 1.372 (4) | C77—H77D | 0.9600 |
C36—C37 | 1.367 (4) | C77—H77E | 0.9600 |
C37—H37 | 0.9300 | C77—H77F | 0.9600 |
C37—C38 | 1.371 (4) | C77—C78A | 1.409 (11) |
C38—H38 | 0.9300 | C77—C78B | 1.512 (17) |
S3—C39 | 1.816 (3) | C79—H79A | 0.9600 |
S3—C42 | 1.744 (3) | C79—H79B | 0.9600 |
O7—C40 | 1.225 (3) | C79—H79C | 0.9600 |
O8—N9 | 1.209 (3) | C79—H79D | 0.9600 |
O9—N9 | 1.207 (3) | C79—H79E | 0.9600 |
N7—C39 | 1.464 (3) | C79—H79F | 0.9600 |
N7—C40 | 1.370 (3) | C79—C78A | 1.496 (10) |
N7—C46 | 1.441 (4) | C79—C78B | 1.371 (13) |
N8—C42 | 1.338 (4) | O14—H14A | 0.8499 |
N8—C43 | 1.331 (4) | O14—H14B | 0.8501 |
N9—C55 | 1.468 (4) | C78A—H78A | 0.9800 |
C39—H39 | 0.9800 | C78B—H78B | 0.9800 |
C4—S1—C1 | 97.70 (12) | N8—C42—S3 | 114.8 (2) |
C2—N1—C1 | 122.3 (2) | N8—C42—C41 | 123.8 (3) |
C2—N1—C8 | 119.9 (2) | C41—C42—S3 | 121.4 (2) |
C8—N1—C1 | 117.4 (2) | N8—C43—H43 | 117.8 |
C5—N2—C4 | 117.3 (2) | N8—C43—C44 | 124.3 (3) |
O2—N3—C17 | 118.0 (3) | C44—C43—H43 | 117.8 |
O3—N3—O2 | 123.6 (3) | C43—C44—H44 | 120.5 |
O3—N3—C17 | 118.4 (3) | C43—C44—C45 | 119.0 (3) |
S1—C1—H1 | 105.8 | C45—C44—H44 | 120.5 |
N1—C1—S1 | 112.14 (18) | C41—C45—H45 | 120.6 |
N1—C1—H1 | 105.8 | C44—C45—C41 | 118.9 (3) |
N1—C1—C14 | 115.6 (2) | C44—C45—H45 | 120.6 |
C14—C1—S1 | 110.95 (18) | C47—C46—N7 | 119.8 (3) |
C14—C1—H1 | 105.8 | C47—C46—C51 | 120.4 (3) |
O1—C2—N1 | 122.1 (2) | C51—C46—N7 | 119.8 (3) |
O1—C2—C3 | 120.1 (2) | C46—C47—H47 | 120.3 |
N1—C2—C3 | 117.8 (2) | C46—C47—C48 | 119.4 (4) |
C4—C3—C2 | 124.1 (2) | C48—C47—H47 | 120.3 |
C7—C3—C2 | 117.8 (2) | C47—C48—H48 | 119.8 |
C7—C3—C4 | 117.7 (3) | C49—C48—C47 | 120.3 (4) |
N2—C4—S1 | 115.1 (2) | C49—C48—H48 | 119.8 |
N2—C4—C3 | 123.2 (3) | C48—C49—H49 | 120.2 |
C3—C4—S1 | 121.7 (2) | C50—C49—C48 | 119.6 (4) |
N2—C5—H5 | 118.1 | C50—C49—H49 | 120.2 |
N2—C5—C6 | 123.9 (3) | C49—C50—H50 | 119.7 |
C6—C5—H5 | 118.1 | C49—C50—C51 | 120.6 (4) |
C5—C6—H6 | 120.7 | C51—C50—H50 | 119.7 |
C5—C6—C7 | 118.7 (3) | C46—C51—H51 | 120.2 |
C7—C6—H6 | 120.7 | C50—C51—C46 | 119.7 (3) |
C3—C7—H7 | 120.4 | C50—C51—H51 | 120.2 |
C6—C7—C3 | 119.2 (3) | C53—C52—C39 | 122.3 (2) |
C6—C7—H7 | 120.4 | C53—C52—C57 | 118.5 (3) |
C9—C8—N1 | 120.9 (3) | C57—C52—C39 | 119.2 (2) |
C9—C8—C13 | 119.3 (3) | C52—C53—H53 | 119.7 |
C13—C8—N1 | 119.8 (3) | C54—C53—C52 | 120.6 (3) |
C8—C9—H9 | 119.9 | C54—C53—H53 | 119.7 |
C10—C9—C8 | 120.2 (3) | C53—C54—H54 | 120.4 |
C10—C9—H9 | 119.9 | C55—C54—C53 | 119.2 (3) |
C9—C10—H10 | 119.8 | C55—C54—H54 | 120.4 |
C11—C10—C9 | 120.4 (3) | C54—C55—N9 | 118.1 (3) |
C11—C10—H10 | 119.8 | C54—C55—C56 | 122.0 (3) |
C10—C11—H11 | 120.1 | C56—C55—N9 | 119.8 (3) |
C10—C11—C12 | 119.8 (3) | C55—C56—H56 | 121.0 |
C12—C11—H11 | 120.1 | C57—C56—C55 | 118.1 (3) |
C11—C12—H12 | 119.9 | C57—C56—H56 | 121.0 |
C11—C12—C13 | 120.2 (3) | C52—C57—H57 | 119.2 |
C13—C12—H12 | 119.9 | C56—C57—C52 | 121.6 (3) |
C8—C13—H13 | 120.0 | C56—C57—H57 | 119.2 |
C12—C13—C8 | 120.1 (3) | C61—S4—C58 | 97.01 (14) |
C12—C13—H13 | 120.0 | C59—N10—C58 | 122.4 (2) |
C15—C14—C1 | 118.0 (2) | C59—N10—C65 | 119.7 (2) |
C19—C14—C1 | 123.5 (2) | C65—N10—C58 | 117.8 (2) |
C19—C14—C15 | 118.5 (3) | C62—N11—C61 | 116.9 (3) |
C14—C15—H15 | 119.3 | O11—N12—O12 | 124.0 (3) |
C16—C15—C14 | 121.5 (3) | O11—N12—C74 | 117.6 (4) |
C16—C15—H15 | 119.3 | O12—N12—C74 | 118.3 (4) |
C15—C16—H16 | 120.8 | S4—C58—H58 | 106.5 |
C17—C16—C15 | 118.5 (3) | N10—C58—S4 | 111.63 (19) |
C17—C16—H16 | 120.8 | N10—C58—H58 | 106.5 |
C16—C17—N3 | 118.7 (3) | N10—C58—C71 | 114.8 (2) |
C18—C17—N3 | 119.3 (3) | C71—C58—S4 | 110.50 (18) |
C18—C17—C16 | 122.0 (3) | C71—C58—H58 | 106.5 |
C17—C18—H18 | 120.4 | O10—C59—N10 | 121.8 (3) |
C17—C18—C19 | 119.2 (3) | O10—C59—C60 | 120.9 (3) |
C19—C18—H18 | 120.4 | N10—C59—C60 | 117.2 (3) |
C14—C19—H19 | 119.8 | C61—C60—C59 | 124.3 (3) |
C18—C19—C14 | 120.4 (3) | C64—C60—C59 | 118.1 (3) |
C18—C19—H19 | 119.8 | C64—C60—C61 | 117.2 (3) |
C23—S2—C20 | 97.49 (13) | N11—C61—S4 | 114.7 (2) |
C21—N4—C20 | 121.7 (2) | N11—C61—C60 | 123.8 (3) |
C21—N4—C27 | 119.5 (2) | C60—C61—S4 | 121.4 (2) |
C27—N4—C20 | 118.6 (2) | N11—C62—H62 | 117.9 |
C24—N5—C23 | 117.0 (3) | N11—C62—C63 | 124.3 (3) |
O5—N6—C36 | 118.2 (3) | C63—C62—H62 | 117.9 |
O6—N6—O5 | 124.1 (3) | C62—C63—H63 | 120.9 |
O6—N6—C36 | 117.7 (3) | C62—C63—C64 | 118.2 (3) |
S2—C20—H20 | 105.9 | C64—C63—H63 | 120.9 |
N4—C20—S2 | 112.10 (19) | C60—C64—H64 | 120.3 |
N4—C20—H20 | 105.9 | C63—C64—C60 | 119.4 (3) |
N4—C20—C33 | 115.2 (2) | C63—C64—H64 | 120.3 |
C33—C20—S2 | 111.0 (2) | C66—C65—N10 | 119.1 (3) |
C33—C20—H20 | 105.9 | C70—C65—N10 | 120.2 (3) |
O4—C21—N4 | 121.1 (3) | C70—C65—C66 | 120.7 (3) |
O4—C21—C22 | 120.7 (2) | C65—C66—H66 | 120.4 |
N4—C21—C22 | 118.2 (2) | C67—C66—C65 | 119.3 (4) |
C23—C22—C21 | 123.7 (3) | C67—C66—H66 | 120.4 |
C26—C22—C21 | 119.2 (2) | C66—C67—H67 | 119.9 |
C26—C22—C23 | 116.7 (3) | C68—C67—C66 | 120.2 (4) |
N5—C23—S2 | 114.6 (2) | C68—C67—H67 | 119.9 |
N5—C23—C22 | 123.7 (3) | C67—C68—H68 | 119.9 |
C22—C23—S2 | 121.6 (2) | C69—C68—C67 | 120.2 (4) |
N5—C24—H24 | 118.0 | C69—C68—H68 | 119.9 |
N5—C24—C25 | 124.0 (3) | C68—C69—H69 | 119.6 |
C25—C24—H24 | 118.0 | C68—C69—C70 | 120.8 (4) |
C24—C25—H25 | 120.8 | C70—C69—H69 | 119.6 |
C24—C25—C26 | 118.3 (3) | C65—C70—C69 | 118.9 (3) |
C26—C25—H25 | 120.8 | C65—C70—H70 | 120.6 |
C22—C26—H26 | 120.0 | C69—C70—H70 | 120.6 |
C25—C26—C22 | 120.0 (3) | C72—C71—C58 | 123.0 (2) |
C25—C26—H26 | 120.0 | C72—C71—C76 | 118.4 (3) |
C28—C27—N4 | 119.6 (3) | C76—C71—C58 | 118.6 (2) |
C28—C27—C32 | 119.9 (3) | C71—C72—H72 | 119.5 |
C32—C27—N4 | 120.5 (3) | C73—C72—C71 | 120.9 (3) |
C27—C28—H28 | 120.3 | C73—C72—H72 | 119.5 |
C29—C28—C27 | 119.4 (4) | C72—C73—H73 | 120.6 |
C29—C28—H28 | 120.3 | C74—C73—C72 | 118.9 (3) |
C28—C29—H29 | 119.7 | C74—C73—H73 | 120.6 |
C30—C29—C28 | 120.6 (4) | C73—C74—N12 | 119.8 (3) |
C30—C29—H29 | 119.7 | C73—C74—C75 | 121.8 (3) |
C29—C30—H30 | 119.9 | C75—C74—N12 | 118.4 (3) |
C31—C30—C29 | 120.2 (4) | C74—C75—H75 | 120.6 |
C31—C30—H30 | 119.9 | C76—C75—C74 | 118.7 (3) |
C30—C31—H31 | 119.9 | C76—C75—H75 | 120.6 |
C30—C31—C32 | 120.1 (4) | C71—C76—H76 | 119.3 |
C32—C31—H31 | 119.9 | C75—C76—C71 | 121.3 (3) |
C27—C32—H32 | 120.1 | C75—C76—H76 | 119.3 |
C31—C32—C27 | 119.8 (3) | C78A—O13—H13A | 109.5 |
C31—C32—H32 | 120.1 | C78B—O13—H13B | 109.5 |
C34—C33—C20 | 123.3 (2) | H77A—C77—H77B | 109.5 |
C34—C33—C38 | 118.5 (3) | H77A—C77—H77C | 109.5 |
C38—C33—C20 | 118.2 (2) | H77B—C77—H77C | 109.5 |
C33—C34—H34 | 119.6 | H77D—C77—H77E | 109.5 |
C35—C34—C33 | 120.9 (3) | H77D—C77—H77F | 109.5 |
C35—C34—H34 | 119.6 | H77E—C77—H77F | 109.5 |
C34—C35—H35 | 120.7 | C78A—C77—H77A | 109.5 |
C36—C35—C34 | 118.6 (3) | C78A—C77—H77B | 109.5 |
C36—C35—H35 | 120.7 | C78A—C77—H77C | 109.5 |
C35—C36—N6 | 119.6 (3) | C78B—C77—H77D | 109.5 |
C37—C36—N6 | 118.2 (3) | C78B—C77—H77E | 109.5 |
C37—C36—C35 | 122.2 (3) | C78B—C77—H77F | 109.5 |
C36—C37—H37 | 120.6 | H79A—C79—H79B | 109.5 |
C36—C37—C38 | 118.8 (3) | H79A—C79—H79C | 109.5 |
C38—C37—H37 | 120.6 | H79B—C79—H79C | 109.5 |
C33—C38—H38 | 119.5 | H79D—C79—H79E | 109.5 |
C37—C38—C33 | 121.0 (3) | H79D—C79—H79F | 109.5 |
C37—C38—H38 | 119.5 | H79E—C79—H79F | 109.5 |
C42—S3—C39 | 97.62 (13) | C78A—C79—H79A | 109.5 |
C40—N7—C39 | 121.1 (2) | C78A—C79—H79B | 109.5 |
C40—N7—C46 | 120.7 (2) | C78A—C79—H79C | 109.5 |
C46—N7—C39 | 117.3 (2) | C78B—C79—H79D | 109.5 |
C43—N8—C42 | 116.2 (3) | C78B—C79—H79E | 109.5 |
O8—N9—C55 | 118.8 (3) | C78B—C79—H79F | 109.5 |
O9—N9—O8 | 122.5 (3) | H14A—O14—H14B | 109.5 |
O9—N9—C55 | 118.7 (3) | O13—C78A—C79 | 110.4 (7) |
S3—C39—H39 | 106.1 | O13—C78A—H78A | 103.9 |
N7—C39—S3 | 112.11 (19) | C77—C78A—O13 | 114.2 (8) |
N7—C39—H39 | 106.1 | C77—C78A—C79 | 118.5 (9) |
N7—C39—C52 | 114.1 (2) | C77—C78A—H78A | 103.9 |
C52—C39—S3 | 111.63 (19) | C79—C78A—H78A | 103.9 |
C52—C39—H39 | 106.1 | O13—C78B—H78B | 108.6 |
O7—C40—N7 | 122.3 (3) | C77—C78B—O13 | 101.2 (12) |
O7—C40—C41 | 119.4 (3) | C77—C78B—H78B | 108.6 |
N7—C40—C41 | 118.3 (2) | C79—C78B—O13 | 109.3 (9) |
C42—C41—C40 | 123.9 (3) | C79—C78B—C77 | 119.9 (10) |
C45—C41—C40 | 118.2 (3) | C79—C78B—H78B | 108.6 |
C45—C41—C42 | 117.7 (3) | ||
S1—C1—C14—C15 | 68.1 (3) | S3—C39—C52—C53 | −108.1 (3) |
S1—C1—C14—C19 | −114.3 (3) | S3—C39—C52—C57 | 72.3 (3) |
O1—C2—C3—C4 | 157.9 (3) | O7—C40—C41—C42 | 159.3 (3) |
O1—C2—C3—C7 | −15.1 (4) | O7—C40—C41—C45 | −14.5 (4) |
O2—N3—C17—C16 | −163.6 (3) | O8—N9—C55—C54 | 9.4 (4) |
O2—N3—C17—C18 | 17.5 (4) | O8—N9—C55—C56 | −169.0 (3) |
O3—N3—C17—C16 | 15.8 (4) | O9—N9—C55—C54 | −171.6 (3) |
O3—N3—C17—C18 | −163.1 (3) | O9—N9—C55—C56 | 10.1 (4) |
N1—C1—C14—C15 | −162.7 (2) | N7—C39—C52—C53 | 20.3 (4) |
N1—C1—C14—C19 | 14.9 (4) | N7—C39—C52—C57 | −159.4 (3) |
N1—C2—C3—C4 | −20.3 (4) | N7—C40—C41—C42 | −19.5 (4) |
N1—C2—C3—C7 | 166.7 (2) | N7—C40—C41—C45 | 166.7 (2) |
N1—C8—C9—C10 | −179.1 (2) | N7—C46—C47—C48 | 179.3 (3) |
N1—C8—C13—C12 | 178.5 (3) | N7—C46—C51—C50 | 179.4 (3) |
N2—C5—C6—C7 | 3.0 (5) | N8—C43—C44—C45 | 3.7 (5) |
N3—C17—C18—C19 | 178.1 (2) | N9—C55—C56—C57 | 178.5 (3) |
C1—S1—C4—N2 | −156.8 (2) | C39—S3—C42—N8 | −157.9 (2) |
C1—S1—C4—C3 | 26.2 (2) | C39—S3—C42—C41 | 25.0 (3) |
C1—N1—C2—O1 | 170.8 (2) | C39—N7—C40—O7 | 167.4 (3) |
C1—N1—C2—C3 | −11.1 (4) | C39—N7—C40—C41 | −13.8 (4) |
C1—N1—C8—C9 | 134.7 (3) | C39—N7—C46—C47 | −36.5 (4) |
C1—N1—C8—C13 | −43.3 (3) | C39—N7—C46—C51 | 142.6 (3) |
C1—C14—C15—C16 | 177.7 (2) | C39—C52—C53—C54 | 179.7 (3) |
C1—C14—C19—C18 | −178.3 (2) | C39—C52—C57—C56 | 179.5 (3) |
C2—N1—C1—S1 | 49.1 (3) | C40—N7—C39—S3 | 52.1 (3) |
C2—N1—C1—C14 | −79.4 (3) | C40—N7—C39—C52 | −76.0 (3) |
C2—N1—C8—C9 | −52.5 (3) | C40—N7—C46—C47 | 132.7 (3) |
C2—N1—C8—C13 | 129.5 (3) | C40—N7—C46—C51 | −48.2 (4) |
C2—C3—C4—S1 | 6.5 (4) | C40—C41—C42—S3 | 7.8 (4) |
C2—C3—C4—N2 | −170.2 (2) | C40—C41—C42—N8 | −169.0 (3) |
C2—C3—C7—C6 | 171.8 (3) | C40—C41—C45—C44 | 171.5 (3) |
C4—S1—C1—N1 | −50.9 (2) | C42—S3—C39—N7 | −52.0 (2) |
C4—S1—C1—C14 | 80.10 (19) | C42—S3—C39—C52 | 77.5 (2) |
C4—N2—C5—C6 | −1.9 (4) | C42—N8—C43—C44 | −1.7 (5) |
C4—C3—C7—C6 | −1.7 (4) | C42—C41—C45—C44 | −2.7 (4) |
C5—N2—C4—S1 | −178.0 (2) | C43—N8—C42—S3 | −179.6 (2) |
C5—N2—C4—C3 | −1.1 (4) | C43—N8—C42—C41 | −2.7 (4) |
C5—C6—C7—C3 | −1.0 (4) | C43—C44—C45—C41 | −1.2 (5) |
C7—C3—C4—S1 | 179.6 (2) | C45—C41—C42—S3 | −178.4 (2) |
C7—C3—C4—N2 | 2.9 (4) | C45—C41—C42—N8 | 4.9 (4) |
C8—N1—C1—S1 | −138.2 (2) | C46—N7—C39—S3 | −138.7 (2) |
C8—N1—C1—C14 | 93.2 (3) | C46—N7—C39—C52 | 93.1 (3) |
C8—N1—C2—O1 | −1.7 (4) | C46—N7—C40—O7 | −1.4 (4) |
C8—N1—C2—C3 | 176.5 (2) | C46—N7—C40—C41 | 177.4 (2) |
C8—C9—C10—C11 | 1.0 (4) | C46—C47—C48—C49 | 1.4 (5) |
C9—C8—C13—C12 | 0.5 (4) | C47—C46—C51—C50 | −1.5 (4) |
C9—C10—C11—C12 | −0.2 (5) | C47—C48—C49—C50 | −1.7 (6) |
C10—C11—C12—C13 | −0.5 (5) | C48—C49—C50—C51 | 0.5 (6) |
C11—C12—C13—C8 | 0.4 (5) | C49—C50—C51—C46 | 1.1 (5) |
C13—C8—C9—C10 | −1.2 (4) | C51—C46—C47—C48 | 0.2 (5) |
C14—C15—C16—C17 | 0.3 (4) | C52—C53—C54—C55 | 1.2 (4) |
C15—C14—C19—C18 | −0.7 (4) | C53—C52—C57—C56 | −0.2 (4) |
C15—C16—C17—N3 | −178.8 (2) | C53—C54—C55—N9 | −179.3 (2) |
C15—C16—C17—C18 | 0.1 (4) | C53—C54—C55—C56 | −1.0 (4) |
C16—C17—C18—C19 | −0.7 (4) | C54—C55—C56—C57 | 0.2 (4) |
C17—C18—C19—C14 | 1.1 (4) | C55—C56—C57—C52 | 0.4 (4) |
C19—C14—C15—C16 | 0.0 (4) | C57—C52—C53—C54 | −0.7 (4) |
S2—C20—C33—C34 | 123.0 (3) | S4—C58—C71—C72 | 124.5 (2) |
S2—C20—C33—C38 | −57.6 (3) | S4—C58—C71—C76 | −57.2 (3) |
O4—C21—C22—C23 | −157.5 (3) | O10—C59—C60—C61 | −156.1 (3) |
O4—C21—C22—C26 | 15.0 (4) | O10—C59—C60—C64 | 16.3 (4) |
O5—N6—C36—C35 | −173.3 (3) | O11—N12—C74—C73 | 6.5 (5) |
O5—N6—C36—C37 | 8.4 (4) | O11—N12—C74—C75 | −171.6 (3) |
O6—N6—C36—C35 | 6.9 (4) | O12—N12—C74—C73 | −173.4 (3) |
O6—N6—C36—C37 | −171.5 (3) | O12—N12—C74—C75 | 8.6 (4) |
N4—C20—C33—C34 | −5.7 (4) | N10—C58—C71—C72 | −2.8 (4) |
N4—C20—C33—C38 | 173.7 (2) | N10—C58—C71—C76 | 175.5 (2) |
N4—C21—C22—C23 | 20.9 (4) | N10—C59—C60—C61 | 21.7 (4) |
N4—C21—C22—C26 | −166.6 (2) | N10—C59—C60—C64 | −165.9 (2) |
N4—C27—C28—C29 | 179.8 (3) | N10—C65—C66—C67 | 178.4 (3) |
N4—C27—C32—C31 | −179.2 (3) | N10—C65—C70—C69 | −178.0 (3) |
N5—C24—C25—C26 | −4.6 (5) | N11—C62—C63—C64 | −4.4 (5) |
N6—C36—C37—C38 | 176.7 (2) | N12—C74—C75—C76 | 177.7 (3) |
C20—S2—C23—N5 | 158.5 (2) | C58—S4—C61—N11 | 156.2 (2) |
C20—S2—C23—C22 | −24.2 (2) | C58—S4—C61—C60 | −26.0 (3) |
C20—N4—C21—O4 | −168.9 (2) | C58—N10—C59—O10 | −170.6 (3) |
C20—N4—C21—C22 | 12.7 (4) | C58—N10—C59—C60 | 11.6 (4) |
C20—N4—C27—C28 | −122.6 (3) | C58—N10—C65—C66 | −119.8 (3) |
C20—N4—C27—C32 | 56.4 (3) | C58—N10—C65—C70 | 58.7 (4) |
C20—C33—C34—C35 | 177.5 (3) | C58—C71—C72—C73 | 178.1 (3) |
C20—C33—C38—C37 | −177.9 (3) | C58—C71—C76—C75 | −178.6 (3) |
C21—N4—C20—S2 | −51.3 (3) | C59—N10—C58—S4 | −51.2 (3) |
C21—N4—C20—C33 | 76.9 (3) | C59—N10—C58—C71 | 75.6 (3) |
C21—N4—C27—C28 | 62.0 (4) | C59—N10—C65—C66 | 63.2 (4) |
C21—N4—C27—C32 | −119.1 (3) | C59—N10—C65—C70 | −118.4 (3) |
C21—C22—C23—S2 | −9.0 (4) | C59—C60—C61—S4 | −8.1 (4) |
C21—C22—C23—N5 | 168.0 (3) | C59—C60—C61—N11 | 169.4 (3) |
C21—C22—C26—C25 | −171.3 (2) | C59—C60—C64—C63 | −172.3 (3) |
C23—S2—C20—N4 | 51.1 (2) | C61—S4—C58—N10 | 52.1 (2) |
C23—S2—C20—C33 | −79.2 (2) | C61—S4—C58—C71 | −76.9 (2) |
C23—N5—C24—C25 | 1.9 (4) | C61—N11—C62—C63 | 2.2 (5) |
C23—C22—C26—C25 | 1.7 (4) | C61—C60—C64—C63 | 0.7 (4) |
C24—N5—C23—S2 | −179.9 (2) | C62—N11—C61—S4 | 179.4 (2) |
C24—N5—C23—C22 | 2.9 (4) | C62—N11—C61—C60 | 1.7 (4) |
C24—C25—C26—C22 | 2.6 (4) | C62—C63—C64—C60 | 2.8 (5) |
C26—C22—C23—S2 | 178.3 (2) | C64—C60—C61—S4 | 179.4 (2) |
C26—C22—C23—N5 | −4.6 (4) | C64—C60—C61—N11 | −3.1 (4) |
C27—N4—C20—S2 | 133.4 (2) | C65—N10—C58—S4 | 131.9 (2) |
C27—N4—C20—C33 | −98.5 (3) | C65—N10—C58—C71 | −101.4 (3) |
C27—N4—C21—O4 | 6.4 (4) | C65—N10—C59—O10 | 6.3 (4) |
C27—N4—C21—C22 | −172.0 (2) | C65—N10—C59—C60 | −171.5 (2) |
C27—C28—C29—C30 | −0.9 (5) | C65—C66—C67—C68 | −0.8 (6) |
C28—C27—C32—C31 | −0.3 (4) | C66—C65—C70—C69 | 0.4 (5) |
C28—C29—C30—C31 | 0.4 (6) | C66—C67—C68—C69 | 1.3 (6) |
C29—C30—C31—C32 | 0.1 (5) | C67—C68—C69—C70 | −0.9 (5) |
C30—C31—C32—C27 | −0.2 (5) | C68—C69—C70—C65 | 0.1 (5) |
C32—C27—C28—C29 | 0.9 (5) | C70—C65—C66—C67 | 0.0 (5) |
C33—C34—C35—C36 | 0.5 (4) | C71—C72—C73—C74 | 0.3 (4) |
C34—C33—C38—C37 | 1.5 (4) | C72—C71—C76—C75 | −0.3 (4) |
C34—C35—C36—N6 | −177.0 (2) | C72—C73—C74—N12 | −178.1 (3) |
C34—C35—C36—C37 | 1.3 (4) | C72—C73—C74—C75 | −0.1 (5) |
C35—C36—C37—C38 | −1.7 (4) | C73—C74—C75—C76 | −0.3 (5) |
C36—C37—C38—C33 | 0.2 (4) | C74—C75—C76—C71 | 0.5 (4) |
C38—C33—C34—C35 | −1.9 (4) | C76—C71—C72—C73 | −0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O13 | 0.98 | 2.49 | 3.461 (4) | 172 |
C6—H6···N5i | 0.93 | 2.74 | 3.431 (4) | 132 |
C39—H39···O14ii | 0.98 | 2.41 | 3.339 (10) | 158 |
C44—H44···N11iii | 0.93 | 2.77 | 3.479 (4) | 134 |
C48—H48···O14 | 0.93 | 2.29 | 3.065 (12) | 141 |
C50—H50···O2iv | 0.93 | 2.62 | 3.412 (5) | 144 |
C58—H58···O7v | 0.98 | 2.49 | 3.246 (3) | 134 |
C76—H76···O7v | 0.93 | 2.78 | 3.498 (4) | 135 |
C79—H79A···O9ii | 0.96 | 2.57 | 3.353 (6) | 138 |
C79—H79E···O8vi | 0.96 | 2.61 | 3.455 (5) | 147 |
C79—H79F···O2iv | 0.96 | 2.75 | 3.493 (6) | 135 |
O13—H13B···O4vii | 0.82 | 1.95 | 2.766 (3) | 176 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z+1; (iv) −x, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y−1, z; (vii) −x+1, −y, −z+1. |
Acknowledgements
We thank Euticals (AMRI) for the gift of T3P in 2-methyltetrahydrofuran, Oakwood Chemicals for thionicotinic acid, and Penn State Schuylkill for financial support.
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