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ISSN: 2056-9890

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 September 2019; accepted 9 October 2019; online 22 October 2019)

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 asymmetric unit. 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 (ππ 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[Arya, K., Tomar, P. & Singh, J. (2014). RSC Adv. 4, 3060-3064.]), anti­bacterial (Shreedhara et al., 2017[Shreedhara, S. H., Vagdevi, H. M., Jayanna, N. D. & Raghavendra, R. (2017). Int. J. Pharma Res. Health Sci. 56, 2055-2063.]), and glycosidase inhibitory (Li et al., 2012[Li, X., Qin, Z., Yang, T., Zhang, H., Wei, S., Li, C., Chen, H. & Meng, M. (2012). Bioorg. Med. Chem. Lett. 22, 2712-2716.]) 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[Yennawar, H. P., Singh, H. & Silverberg, L. J. (2014). Acta Cryst. E70, o638.]). 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.

[Scheme 1]

2. Structural commentary

The asymmetric unit of 1 (Fig. 1[link]) 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[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), 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 asymmetric unit, it has an S configuration, but crystal symmetry generates a racemic mixture.

[Figure 1]
Figure 1
The asymmetric unit of 1 with the solvent toluene mol­ecule straddling the inversion center. The displacement ellipsoids are drawn at the 50% probability level.

In 2, the configurations of the stereogenic centers in the four arbitrarily chosen independent thia­zine mol­ecules A, B, C, and D (Fig. 2[link]) 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 asymmetric unit. The puckering of the thia­zine ring in each case is an envelope (Q ∼ 55 Å, θ ∼ 65°, and φ ∼ 41°, considering chirality 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[link]). 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[link]) also shows very little discrepancy.

[Figure 2]
Figure 2
The asymmetric unit of 2 with solvent 2-propanol and water (0.25 occupancy) mol­ecules. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 3]
Figure 3
Overlay image for two pairs of enanti­omers in the asymmetric unit of 2, showing the overall structural similarity.
[Figure 4]
Figure 4
Overlay image showing the similarity of the structures of 1 and 2.

3. Supra­molecular features

The asymmetric unit of 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[link] and Fig. 5[link]). 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 ππ parallel stacking is observed in this structure.

Table 1
Hydrogen-bond geometry (Å, °) for 1[link]

D—H⋯A D—H H⋯A DA 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-{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 5]
Figure 5
Packing diagram for 1, showing the C—H⋯N(π) and C—H⋯O `reciprocal-pair' of hydrogen bonds.

Within the asymmetric unit of 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[link]). 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[link]) 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.

Table 2
Hydrogen-bond geometry (Å, °) for 2[link]

D—H⋯A D—H H⋯A DA 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.
[Figure 6]
Figure 6
Packing diagram for 2, showing the aromatic ring stacking interactions along with the C—H⋯N(π) and C—H⋯O hydrogen bonds.

4. Database survey

Along with the previously mentioned structure (Yennawar et al., 2014[Yennawar, H. P., Singh, H. & Silverberg, L. J. (2014). Acta Cryst. E70, o638.]), we have published a structure of the sulfoxide derivative (Yennawar et al. 2017[Yennawar, H. P., Noble, D. J., Yang, Z. & Silverberg, L. J. (2017). IUCrData, 2, x171112.]). 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 thin-layer chromatography (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 refinement details are summarized in Table 3[link]. 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).

Table 3
Experimental details

  1 2
Crystal data
Chemical formula C19H13FN2OS·0.5C7H8 4C19H13N3O3S·C3H8O·0.25H2O
Mr 382.44 1518.13
Crystal system, space group Monoclinic, P21/c Triclinic, P[\overline{1}]
Temperature (K) 298 298
a, b, c (Å) 14.4481 (16), 9.0141 (10), 16.3427 (19) 12.5451 (13), 15.9804 (17), 19.434 (2)
α, β, γ (°) 90, 115.481 (2), 90 86.671 (2), 72.369 (2), 74.167 (2)
V3) 1921.4 (4) 3570.8 (6)
Z 4 2
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.19 0.21
Crystal size (mm) 0.27 × 0.26 × 0.26 0.19 × 0.18 × 0.03
 
Data collection
Diffractometer Bruker CCD area detector Bruker CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.877, 0.9 0.230, 0.9
No. of measured, independent and observed [I > 2σ(I)] reflections 14808, 4590, 3093 30898, 16372, 7969
Rint 0.026 0.039
(sin θ/λ)max−1) 0.667 0.668
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.151, 1.01 0.057, 0.158, 0.95
No. of reflections 4590 16372
No. of parameters 266 997
No. of restraints 57 30
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.22 0.28, −0.27
Computer programs: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Computing details top

For both structures, data collection: SMART (Bruker, 2001); cell refinement: 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).

2-(4-Fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one toluene hemisolvate (1) top
Crystal data top
C19H13FN2OS·0.5C7H8F(000) = 796
Mr = 382.44Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.4481 (16) ÅCell parameters from 4037 reflections
b = 9.0141 (10) Åθ = 2.5–28.1°
c = 16.3427 (19) ŵ = 0.19 mm1
β = 115.481 (2)°T = 298 K
V = 1921.4 (4) Å3Block, colorless
Z = 40.27 × 0.26 × 0.26 mm
Data collection top
Bruker CCD area detector
diffractometer
4590 independent reflections
Radiation source: fine-focus sealed tube3093 reflections with I > 2σ(I)
Parallel-graphite monochromatorRint = 0.026
Detector resolution: 8.34 pixels mm-1θmax = 28.3°, θmin = 1.6°
phi and ω scansh = 1819
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 1111
Tmin = 0.877, Tmax = 0.9l = 2120
14808 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-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 parametersΔρmax = 0.27 e Å3
57 restraintsΔρmin = 0.22 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.29551 (12)0.63383 (19)0.57705 (12)0.0532 (4)
H10.32120.54510.55890.064*
C20.15230 (13)0.8065 (2)0.49787 (11)0.0556 (4)
C30.21206 (12)0.92059 (18)0.56667 (11)0.0507 (4)
C40.31888 (13)0.9229 (2)0.61149 (12)0.0547 (4)
C50.32028 (19)1.1473 (2)0.67453 (17)0.0801 (6)
H50.35691.22670.71000.096*
C60.21563 (18)1.1539 (2)0.63701 (15)0.0706 (5)
H60.18231.23340.64900.085*
C70.16061 (14)1.0401 (2)0.58099 (12)0.0589 (4)
H70.08941.04350.55290.071*
C80.28175 (12)0.59127 (17)0.66097 (11)0.0504 (4)
C90.36712 (13)0.5528 (2)0.73966 (13)0.0624 (5)
H90.43170.55580.74020.075*
C100.35817 (17)0.5105 (2)0.81643 (14)0.0739 (6)
H100.41580.48540.86880.089*
C110.26220 (19)0.5060 (2)0.81421 (15)0.0738 (6)
C120.17612 (16)0.5385 (2)0.73843 (16)0.0733 (6)
H120.11180.53190.73830.088*
C130.18591 (13)0.5816 (2)0.66148 (14)0.0613 (5)
H130.12750.60460.60920.074*
C140.15587 (12)0.5691 (2)0.42719 (11)0.0550 (4)
C150.13424 (15)0.6091 (2)0.33997 (13)0.0666 (5)
H150.14500.70630.32700.080*
C160.09640 (17)0.5050 (3)0.27128 (14)0.0786 (6)
H160.08070.53300.21200.094*
C170.08185 (15)0.3616 (3)0.28964 (16)0.0788 (6)
H170.05750.29180.24330.095*
C180.10316 (18)0.3212 (3)0.37627 (17)0.0835 (6)
H180.09320.22350.38900.100*
C190.13963 (17)0.4250 (2)0.44561 (14)0.0748 (6)
H190.15310.39720.50450.090*
F10.25250 (13)0.46699 (18)0.89080 (11)0.1126 (5)
N10.20053 (10)0.67498 (16)0.49958 (9)0.0557 (4)
N20.37270 (13)1.03462 (19)0.66340 (13)0.0728 (5)
O10.06489 (10)0.83185 (16)0.44210 (9)0.0744 (4)
S10.39249 (3)0.77650 (6)0.60028 (4)0.06511 (19)
C1A0.4323 (6)0.2876 (5)0.5316 (6)0.246 (7)0.50
H1AA0.45970.27620.59620.369*0.50
H1AB0.44970.20240.50590.369*0.50
H1AC0.35910.29690.50670.369*0.50
C1B0.4768 (3)0.4249 (4)0.5097 (4)0.0998 (16)0.50
C1C0.5654 (3)0.4916 (6)0.5751 (3)0.113 (4)0.50
H1C0.59800.44920.63240.136*0.50
C1D0.6056 (4)0.6207 (6)0.5558 (5)0.136 (3)0.50
H1D0.66440.66360.60000.163*0.50
C1E0.5576 (6)0.6857 (4)0.4700 (5)0.161 (4)0.50
H1E0.58420.77180.45700.193*0.50
C1F0.4695 (5)0.6202 (6)0.4041 (4)0.158 (4)0.50
H1F0.43730.66270.34680.190*0.50
C1G0.4298 (4)0.4911 (6)0.4239 (3)0.136 (5)0.50
H1G0.37110.44840.37950.163*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0436 (8)0.0512 (10)0.0595 (10)0.0101 (7)0.0170 (7)0.0053 (8)
C20.0517 (9)0.0555 (10)0.0561 (10)0.0126 (8)0.0199 (8)0.0024 (8)
C30.0547 (9)0.0457 (9)0.0540 (9)0.0081 (7)0.0255 (7)0.0040 (7)
C40.0544 (9)0.0493 (10)0.0654 (10)0.0003 (7)0.0305 (8)0.0016 (8)
C50.0924 (16)0.0543 (12)0.0949 (16)0.0173 (11)0.0413 (13)0.0139 (11)
C60.0978 (15)0.0452 (11)0.0830 (13)0.0065 (10)0.0523 (12)0.0023 (9)
C70.0667 (11)0.0530 (10)0.0640 (11)0.0125 (8)0.0347 (9)0.0074 (8)
C80.0455 (8)0.0399 (9)0.0597 (9)0.0051 (6)0.0169 (7)0.0067 (7)
C90.0474 (9)0.0641 (12)0.0662 (11)0.0045 (8)0.0152 (8)0.0017 (9)
C100.0749 (13)0.0709 (13)0.0617 (12)0.0033 (10)0.0159 (10)0.0035 (10)
C110.1004 (16)0.0569 (12)0.0735 (13)0.0014 (11)0.0463 (13)0.0014 (9)
C120.0716 (13)0.0608 (13)0.1025 (16)0.0028 (10)0.0515 (12)0.0017 (11)
C130.0476 (9)0.0563 (11)0.0754 (12)0.0080 (8)0.0221 (8)0.0024 (9)
C140.0494 (9)0.0543 (10)0.0550 (10)0.0088 (7)0.0166 (7)0.0053 (8)
C150.0721 (12)0.0670 (12)0.0653 (12)0.0066 (9)0.0339 (10)0.0018 (9)
C160.0800 (14)0.0959 (18)0.0593 (12)0.0108 (12)0.0295 (10)0.0122 (11)
C170.0637 (12)0.0876 (17)0.0733 (14)0.0048 (11)0.0183 (10)0.0297 (12)
C180.0901 (16)0.0613 (13)0.0875 (16)0.0057 (11)0.0271 (12)0.0150 (11)
C190.0892 (14)0.0607 (13)0.0625 (12)0.0023 (10)0.0212 (11)0.0022 (9)
F10.1540 (14)0.1109 (12)0.0960 (10)0.0009 (10)0.0757 (10)0.0084 (8)
N10.0519 (7)0.0490 (8)0.0560 (8)0.0110 (6)0.0135 (6)0.0051 (6)
N20.0672 (10)0.0594 (10)0.0908 (12)0.0135 (8)0.0331 (9)0.0106 (9)
O10.0562 (7)0.0767 (9)0.0685 (8)0.0241 (6)0.0063 (6)0.0078 (7)
S10.0459 (3)0.0666 (3)0.0863 (4)0.0046 (2)0.0318 (2)0.0013 (2)
C1A0.304 (18)0.126 (9)0.42 (2)0.023 (10)0.256 (17)0.003 (11)
C1B0.121 (4)0.067 (3)0.156 (5)0.026 (3)0.102 (4)0.001 (3)
C1C0.128 (10)0.109 (7)0.124 (6)0.021 (6)0.075 (5)0.025 (5)
C1D0.126 (5)0.107 (5)0.228 (8)0.018 (4)0.128 (6)0.053 (5)
C1E0.259 (12)0.059 (4)0.296 (11)0.024 (5)0.244 (10)0.012 (6)
C1F0.280 (11)0.092 (5)0.167 (6)0.087 (6)0.157 (6)0.045 (4)
C1G0.127 (10)0.130 (9)0.151 (8)0.061 (6)0.060 (6)0.004 (6)
Geometric parameters (Å, º) top
C1—H10.9800C14—C151.370 (3)
C1—C81.517 (2)C14—C191.376 (3)
C1—N11.459 (2)C14—N11.439 (2)
C1—S11.8176 (18)C15—H150.9300
C2—C31.494 (2)C15—C161.383 (3)
C2—N11.370 (2)C16—H160.9300
C2—O11.219 (2)C16—C171.363 (3)
C3—C41.395 (2)C17—H170.9300
C3—C71.385 (2)C17—C181.363 (3)
C4—N21.331 (2)C18—H180.9300
C4—S11.7534 (18)C18—C191.387 (3)
C5—H50.9300C19—H190.9300
C5—C61.367 (3)C1A—H1AA0.9600
C5—N21.326 (3)C1A—H1AB0.9600
C6—H60.9300C1A—H1AC0.9600
C6—C71.377 (3)C1A—C1B1.5071
C7—H70.9300C1B—C1C1.4021
C8—C91.390 (2)C1B—C1G1.4020
C8—C131.391 (2)C1C—H1C0.9300
C9—H90.9300C1C—C1D1.3962
C9—C101.370 (3)C1D—H1D0.9300
C10—H100.9300C1D—C1E1.3965
C10—C111.372 (3)C1E—H1E0.9300
C11—C121.357 (3)C1E—C1F1.3964
C11—F11.364 (2)C1F—H1F0.9300
C12—H120.9300C1F—C1G1.3964
C12—C131.381 (3)C1G—H1G0.9300
C13—H130.9300
C8—C1—H1106.4C15—C14—C19119.51 (17)
C8—C1—S1112.28 (11)C15—C14—N1120.08 (17)
N1—C1—H1106.4C19—C14—N1120.32 (16)
N1—C1—C8114.11 (13)C14—C15—H15120.0
N1—C1—S1110.74 (12)C14—C15—C16119.9 (2)
S1—C1—H1106.4C16—C15—H15120.0
N1—C2—C3117.14 (14)C15—C16—H16119.7
O1—C2—C3120.75 (15)C17—C16—C15120.6 (2)
O1—C2—N1122.10 (16)C17—C16—H16119.7
C4—C3—C2123.80 (15)C16—C17—H17120.2
C7—C3—C2118.96 (15)C18—C17—C16119.6 (2)
C7—C3—C4116.90 (16)C18—C17—H17120.2
C3—C4—S1121.16 (13)C17—C18—H18119.8
N2—C4—C3123.87 (17)C17—C18—C19120.4 (2)
N2—C4—S1114.95 (14)C19—C18—H18119.8
C6—C5—H5118.0C14—C19—C18119.9 (2)
N2—C5—H5118.0C14—C19—H19120.0
N2—C5—C6123.96 (19)C18—C19—H19120.0
C5—C6—H6120.8C2—N1—C1121.21 (14)
C5—C6—C7118.49 (19)C2—N1—C14120.90 (14)
C7—C6—H6120.8C14—N1—C1117.80 (13)
C3—C7—H7120.2C5—N2—C4117.11 (18)
C6—C7—C3119.57 (18)C4—S1—C196.13 (8)
C6—C7—H7120.2C1C—C1B—C1A120.9
C9—C8—C1119.36 (15)C1G—C1B—C1A121.0
C9—C8—C13117.94 (17)C1G—C1B—C1C118.1
C13—C8—C1122.62 (15)C1B—C1C—H1C119.4
C8—C9—H9119.3C1D—C1C—C1B121.1
C10—C9—C8121.41 (18)C1D—C1C—H1C119.4
C10—C9—H9119.3C1C—C1D—H1D119.9
C9—C10—H10120.8C1C—C1D—C1E120.1
C9—C10—C11118.47 (19)C1E—C1D—H1D119.9
C11—C10—H10120.8C1D—C1E—H1E120.3
C12—C11—C10122.5 (2)C1F—C1E—C1D119.4
C12—C11—F1118.5 (2)C1F—C1E—H1E120.3
F1—C11—C10119.0 (2)C1E—C1F—H1F119.9
C11—C12—H12120.7C1E—C1F—C1G120.1
C11—C12—C13118.65 (19)C1G—C1F—H1F119.9
C13—C12—H12120.7C1B—C1G—H1G119.5
C8—C13—H13119.5C1F—C1G—C1B121.1
C12—C13—C8121.02 (18)C1F—C1G—H1G119.5
C12—C13—H13119.5
C1—C8—C9—C10178.56 (17)C19—C14—C15—C160.0 (3)
C1—C8—C13—C12178.16 (17)C19—C14—N1—C151.1 (2)
C2—C3—C4—N2170.57 (18)C19—C14—N1—C2125.4 (2)
C2—C3—C4—S17.9 (2)F1—C11—C12—C13178.40 (18)
C2—C3—C7—C6173.19 (17)N1—C1—C8—C9178.73 (15)
C3—C2—N1—C114.2 (2)N1—C1—C8—C134.6 (2)
C3—C2—N1—C14169.48 (15)N1—C1—S1—C455.64 (13)
C3—C4—N2—C52.1 (3)N1—C2—C3—C421.2 (3)
C3—C4—S1—C127.46 (16)N1—C2—C3—C7165.76 (16)
C4—C3—C7—C60.4 (2)N1—C14—C15—C16176.57 (17)
C5—C6—C7—C32.2 (3)N1—C14—C19—C18175.56 (19)
C6—C5—N2—C40.8 (3)N2—C4—S1—C1153.98 (15)
C7—C3—C4—N22.6 (3)N2—C5—C6—C73.0 (3)
C7—C3—C4—S1178.93 (13)O1—C2—C3—C4157.79 (18)
C8—C1—N1—C272.3 (2)O1—C2—C3—C715.3 (3)
C8—C1—N1—C14104.19 (17)O1—C2—N1—C1166.91 (17)
C8—C1—S1—C473.21 (12)O1—C2—N1—C149.4 (3)
C8—C9—C10—C110.3 (3)S1—C1—C8—C951.67 (19)
C9—C8—C13—C121.5 (3)S1—C1—C8—C13131.69 (15)
C9—C10—C11—C121.6 (3)S1—C1—N1—C255.58 (19)
C9—C10—C11—F1178.67 (19)S1—C1—N1—C14127.96 (14)
C10—C11—C12—C131.8 (3)S1—C4—N2—C5179.41 (16)
C11—C12—C13—C80.3 (3)C1A—C1B—C1C—C1D178.5
C13—C8—C9—C101.8 (3)C1A—C1B—C1G—C1F178.5
C14—C15—C16—C171.1 (3)C1B—C1C—C1D—C1E0.1
C15—C14—C19—C181.0 (3)C1C—C1B—C1G—C1F0.3
C15—C14—N1—C1125.51 (18)C1C—C1D—C1E—C1F0.1
C15—C14—N1—C258.0 (2)C1D—C1E—C1F—C1G0.1
C15—C16—C17—C181.1 (3)C1E—C1F—C1G—C1B0.1
C16—C17—C18—C190.1 (3)C1G—C1B—C1C—C1D0.3
C17—C18—C19—C141.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.533.321 (2)143
C9—H9···N2ii0.932.583.398 (2)147
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y1/2, z+3/2.
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) top
Crystal data top
4C19H13N3O3S·C3H8O·0.25H2OZ = 2
Mr = 1518.13F(000) = 1577
Triclinic, P1Dx = 1.412 Mg m3
a = 12.5451 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.9804 (17) ÅCell parameters from 4843 reflections
c = 19.434 (2) Åθ = 2.4–28.2°
α = 86.671 (2)°µ = 0.21 mm1
β = 72.369 (2)°T = 298 K
γ = 74.167 (2)°Plate, colorless
V = 3570.8 (6) Å30.19 × 0.18 × 0.03 mm
Data collection top
Bruker CCD area detector
diffractometer
7969 reflections with I > 2σ(I)
phi and ω scansRint = 0.039
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 28.4°, θmin = 1.3°
Tmin = 0.230, Tmax = 0.9h = 1616
30898 measured reflectionsk = 2020
16372 independent reflectionsl = 2525
Refinement top
Refinement on F230 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057H-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 reflectionsΔρmax = 0.28 e Å3
997 parametersΔρmin = 0.27 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.29218 (6)0.03290 (5)0.18613 (4)0.0501 (2)
O10.04665 (16)0.18932 (12)0.17939 (10)0.0550 (5)
O20.0412 (3)0.27498 (17)0.35233 (15)0.0955 (8)
O30.0788 (3)0.29499 (16)0.41328 (14)0.0907 (8)
N10.06953 (17)0.12964 (14)0.24885 (11)0.0414 (5)
N20.2998 (2)0.01955 (15)0.05960 (13)0.0535 (6)
N30.0313 (3)0.25406 (18)0.37145 (15)0.0632 (7)
C10.1603 (2)0.05663 (17)0.26243 (14)0.0437 (7)
H10.1815100.0764010.3020310.052*
C20.0381 (2)0.13447 (18)0.18683 (14)0.0426 (7)
C30.1134 (2)0.07162 (17)0.12647 (14)0.0415 (6)
C40.2284 (2)0.02717 (18)0.11932 (14)0.0440 (7)
C50.2559 (3)0.0235 (2)0.00611 (17)0.0597 (8)
H50.3049970.0541210.0360140.072*
C60.1422 (3)0.0148 (2)0.00931 (16)0.0580 (8)
H60.1146230.0079520.0287690.070*
C70.0699 (3)0.06374 (19)0.07008 (15)0.0502 (7)
H70.0071330.0911390.0732940.060*
C80.0037 (2)0.19178 (19)0.30682 (15)0.0459 (7)
C90.0185 (2)0.28007 (19)0.29480 (17)0.0504 (7)
H90.0084590.2997600.2484660.060*
C100.0806 (3)0.3390 (2)0.3512 (2)0.0633 (9)
H100.0962700.3983560.3425960.076*
C110.1193 (3)0.3108 (3)0.4201 (2)0.0761 (11)
H110.1610260.3507940.4580100.091*
C120.0963 (3)0.2229 (3)0.43276 (18)0.0784 (11)
H120.1219120.2036690.4794090.094*
C130.0352 (3)0.1633 (2)0.37638 (16)0.0617 (9)
H130.0201900.1040290.3850980.074*
C140.1239 (2)0.02529 (17)0.28802 (14)0.0412 (6)
C150.1940 (2)0.08729 (19)0.32026 (15)0.0518 (8)
H150.2622070.0779370.3236690.062*
C160.1648 (3)0.16179 (19)0.34711 (15)0.0532 (8)
H160.2120760.2026810.3687970.064*
C170.0643 (3)0.17473 (19)0.34131 (14)0.0479 (7)
C180.0068 (3)0.1158 (2)0.30966 (15)0.0532 (8)
H180.0741270.1263980.3058620.064*
C190.0226 (2)0.04033 (19)0.28338 (15)0.0491 (7)
H190.0258360.0006070.2624640.059*
S20.19473 (6)0.08666 (5)0.80114 (5)0.0613 (2)
O40.56806 (17)0.00558 (13)0.70493 (10)0.0574 (5)
O50.2168 (3)0.25409 (17)1.12494 (13)0.0845 (7)
O60.4024 (3)0.20792 (19)1.09163 (13)0.0952 (8)
N40.4121 (2)0.10919 (15)0.74362 (12)0.0500 (6)
N50.2221 (2)0.07471 (19)0.83891 (14)0.0596 (7)
N60.3093 (3)0.22173 (18)1.08058 (15)0.0633 (7)
C200.3005 (2)0.14686 (18)0.79718 (15)0.0498 (7)
H200.2698970.2046310.7799220.060*
C210.4679 (2)0.02283 (19)0.74233 (15)0.0460 (7)
C220.4024 (2)0.03636 (18)0.78632 (14)0.0436 (7)
C230.2810 (2)0.0166 (2)0.81035 (15)0.0496 (7)
C240.2841 (3)0.1547 (2)0.84727 (17)0.0632 (9)
H240.2444230.1963680.8657520.076*
C250.4028 (3)0.1794 (2)0.83030 (17)0.0593 (8)
H250.4418220.2348820.8402960.071*
C260.4626 (3)0.12010 (19)0.79817 (16)0.0518 (7)
H260.5432810.1359610.7843450.062*
C270.4675 (2)0.16600 (19)0.69490 (16)0.0511 (7)
C280.4947 (3)0.1525 (2)0.62135 (17)0.0714 (10)
H280.4774240.1066870.6034970.086*
C290.5478 (3)0.2075 (3)0.5746 (2)0.0849 (12)
H290.5673270.1981670.5250040.102*
C300.5721 (3)0.2757 (3)0.6005 (2)0.0811 (11)
H300.6074500.3126590.5685460.097*
C310.5445 (3)0.2897 (2)0.6732 (2)0.0740 (10)
H310.5609190.3362120.6906740.089*
C320.4921 (3)0.2349 (2)0.72099 (18)0.0605 (8)
H320.4735600.2443280.7705090.073*
C330.3067 (2)0.16168 (17)0.87210 (15)0.0433 (7)
C340.4083 (2)0.13472 (18)0.89128 (16)0.0507 (7)
H340.4762710.1039940.8577720.061*
C350.4099 (3)0.15283 (19)0.95934 (16)0.0544 (8)
H350.4784040.1350450.9719400.065*
C360.3084 (3)0.19765 (18)1.00816 (15)0.0479 (7)
C370.2059 (3)0.22324 (18)0.99185 (16)0.0518 (7)
H370.1378210.2522471.0262390.062*
C380.2052 (2)0.20535 (18)0.92384 (16)0.0493 (7)
H380.1359420.2226430.9120960.059*
S30.48325 (6)0.54203 (5)0.79720 (5)0.0604 (2)
O70.13744 (16)0.53956 (13)0.79718 (11)0.0584 (5)
O80.2856 (3)0.96125 (17)0.64375 (14)0.0961 (9)
O90.4647 (3)0.92989 (18)0.58597 (18)0.1164 (11)
N70.32514 (18)0.52725 (15)0.73153 (12)0.0476 (6)
N80.3661 (2)0.61800 (17)0.92278 (15)0.0650 (7)
N90.3801 (3)0.9097 (2)0.62374 (15)0.0657 (7)
C390.4283 (2)0.55876 (18)0.71966 (16)0.0494 (7)
H390.4888220.5224180.6802020.059*
C400.2314 (2)0.55268 (18)0.79167 (16)0.0479 (7)
C410.2460 (2)0.59634 (18)0.85278 (15)0.0467 (7)
C420.3535 (2)0.59082 (18)0.86259 (16)0.0518 (7)
C430.2685 (4)0.6551 (2)0.97386 (19)0.0726 (10)
H430.2748540.6731131.0167590.087*
C440.1595 (3)0.6684 (2)0.96741 (18)0.0682 (9)
H440.0945360.6976681.0038560.082*
C450.1474 (3)0.63801 (19)0.90639 (16)0.0559 (8)
H450.0741910.6453180.9011850.067*
C460.3174 (2)0.4816 (2)0.67217 (17)0.0519 (8)
C470.3583 (3)0.5075 (2)0.60260 (19)0.0687 (9)
H470.3901370.5546510.5937700.082*
C480.3516 (3)0.4627 (3)0.5459 (2)0.0886 (12)
H480.3805300.4790970.4987150.106*
C490.3020 (3)0.3938 (3)0.5591 (3)0.0927 (13)
H490.2957290.3647850.5210420.111*
C500.2623 (3)0.3685 (3)0.6286 (3)0.0845 (12)
H500.2294800.3218490.6375640.101*
C510.2705 (3)0.4115 (2)0.6853 (2)0.0646 (9)
H510.2446130.3933930.7323510.078*
C520.4134 (2)0.65204 (18)0.69454 (14)0.0442 (7)
C530.3052 (2)0.71039 (19)0.70482 (15)0.0499 (7)
H530.2386030.6926190.7275950.060*
C540.2952 (2)0.79473 (19)0.68155 (15)0.0509 (7)
H540.2225220.8340730.6893470.061*
C550.3930 (3)0.81948 (19)0.64715 (15)0.0492 (7)
C560.5027 (3)0.7632 (2)0.63555 (16)0.0572 (8)
H560.5687630.7812160.6120040.069*
C570.5112 (2)0.6801 (2)0.65971 (16)0.0554 (8)
H570.5843120.6415130.6526240.066*
S40.00824 (6)0.62257 (5)0.19021 (5)0.0601 (2)
O100.27502 (19)0.58431 (14)0.28290 (11)0.0660 (6)
O110.4765 (3)0.3508 (2)0.09779 (15)0.1215 (11)
O120.3228 (3)0.37649 (17)0.13080 (14)0.0992 (9)
N100.1560 (2)0.52364 (15)0.24786 (12)0.0486 (6)
N110.0602 (2)0.76000 (18)0.14094 (15)0.0687 (8)
N120.3728 (3)0.37844 (19)0.08640 (17)0.0780 (9)
C580.0938 (2)0.51872 (18)0.19627 (15)0.0481 (7)
H580.0472990.4776540.2156680.058*
C590.2114 (3)0.5869 (2)0.24570 (16)0.0506 (7)
C600.1878 (2)0.66125 (19)0.19797 (15)0.0479 (7)
C610.0896 (2)0.68606 (19)0.17441 (16)0.0537 (8)
C620.1314 (4)0.8109 (2)0.1284 (2)0.0767 (10)
H620.1106360.8636920.1065340.092*
C630.2332 (3)0.7909 (2)0.14539 (18)0.0709 (10)
H630.2826490.8269760.1324840.085*
C640.2609 (3)0.7155 (2)0.18231 (16)0.0585 (8)
H640.3279430.7012540.1965060.070*
C650.1627 (3)0.4563 (2)0.30032 (17)0.0534 (8)
C660.1160 (3)0.4788 (2)0.37276 (18)0.0774 (10)
H660.0824550.5368720.3875540.093*
C670.1197 (4)0.4145 (3)0.4230 (2)0.0930 (12)
H670.0893170.4292140.4720050.112*
C680.1681 (3)0.3289 (3)0.4009 (2)0.0830 (12)
H680.1689950.2855870.4350300.100*
C690.2145 (3)0.3072 (2)0.3297 (2)0.0749 (10)
H690.2480190.2490890.3152320.090*
C700.2125 (3)0.3707 (2)0.27805 (18)0.0606 (8)
H700.2443780.3556130.2291490.073*
C710.1711 (2)0.48386 (17)0.12155 (14)0.0425 (7)
C720.2909 (2)0.46199 (19)0.10238 (17)0.0545 (8)
H720.3270510.4701720.1357740.065*
C730.3576 (3)0.4282 (2)0.03438 (18)0.0608 (8)
H730.4382230.4133080.0218590.073*
C740.3033 (3)0.41698 (19)0.01417 (16)0.0561 (8)
C750.1842 (3)0.43826 (19)0.00298 (17)0.0591 (8)
H750.1486160.4304090.0308360.071*
C760.1192 (3)0.47116 (18)0.07068 (16)0.0510 (7)
H760.0386870.4853330.0828840.061*
O130.2504 (2)0.10492 (18)0.40343 (12)0.1046 (9)
H13A0.3038040.0613080.3879280.157*0.58 (2)
H13B0.3028010.0769050.3698100.157*0.42 (2)
C770.1668 (5)0.0177 (4)0.4961 (3)0.1325 (18)
H77A0.1099540.0141640.4734470.199*0.58 (2)
H77B0.1351000.0154580.5475770.199*0.58 (2)
H77C0.2345620.0303170.4794760.199*0.58 (2)
H77D0.0927880.0601580.5073240.199*0.42 (2)
H77E0.1716870.0174910.5374160.199*0.42 (2)
H77F0.1752550.0186660.4561350.199*0.42 (2)
C790.2605 (4)0.1265 (3)0.5221 (2)0.1003 (13)
H79A0.3380320.0891620.5117100.150*0.58 (2)
H79B0.2204630.1244430.5725200.150*0.58 (2)
H79C0.2633840.1850850.5099820.150*0.58 (2)
H79D0.3240910.1513220.5004450.150*0.42 (2)
H79E0.2673260.1012100.5670840.150*0.42 (2)
H79F0.1885910.1711080.5305630.150*0.42 (2)
O140.3199 (9)0.5360 (8)0.4020 (6)0.099 (3)0.25
H14A0.2835020.5008540.4260310.148*0.25
H14B0.2773310.5878670.4116470.148*0.25
C78A0.1974 (14)0.0965 (10)0.4784 (4)0.077 (3)0.58 (2)
H78A0.1225750.1406450.4888870.092*0.58 (2)
C78B0.2625 (18)0.0633 (10)0.4765 (6)0.079 (4)0.42 (2)
H78B0.3373430.0193260.4668780.095*0.42 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0371 (4)0.0596 (5)0.0533 (5)0.0121 (3)0.0145 (3)0.0032 (4)
O10.0471 (11)0.0562 (13)0.0612 (13)0.0020 (10)0.0250 (10)0.0045 (10)
O20.118 (2)0.092 (2)0.104 (2)0.0665 (18)0.0394 (18)0.0080 (16)
O30.134 (2)0.0693 (17)0.0782 (18)0.0354 (16)0.0412 (17)0.0227 (14)
N10.0405 (12)0.0433 (13)0.0402 (13)0.0069 (10)0.0150 (10)0.0031 (11)
N20.0485 (14)0.0568 (16)0.0490 (15)0.0128 (12)0.0063 (12)0.0020 (13)
N30.085 (2)0.0573 (18)0.0483 (17)0.0295 (16)0.0111 (15)0.0055 (14)
C10.0409 (15)0.0486 (17)0.0448 (16)0.0104 (13)0.0186 (13)0.0010 (13)
C20.0393 (15)0.0488 (17)0.0439 (17)0.0152 (13)0.0152 (13)0.0003 (14)
C30.0432 (15)0.0438 (16)0.0396 (16)0.0157 (13)0.0117 (13)0.0010 (13)
C40.0409 (15)0.0452 (17)0.0428 (16)0.0136 (13)0.0063 (13)0.0031 (14)
C50.062 (2)0.067 (2)0.0471 (19)0.0188 (17)0.0077 (16)0.0118 (16)
C60.065 (2)0.070 (2)0.0433 (18)0.0245 (17)0.0152 (16)0.0056 (16)
C70.0505 (17)0.0538 (18)0.0510 (18)0.0192 (14)0.0174 (15)0.0014 (15)
C80.0388 (15)0.0519 (19)0.0466 (18)0.0087 (13)0.0141 (13)0.0063 (15)
C90.0445 (16)0.0509 (19)0.0591 (19)0.0116 (14)0.0201 (15)0.0054 (16)
C100.0559 (19)0.056 (2)0.076 (2)0.0039 (16)0.0243 (18)0.0153 (19)
C110.065 (2)0.081 (3)0.072 (3)0.006 (2)0.022 (2)0.032 (2)
C120.082 (3)0.089 (3)0.048 (2)0.001 (2)0.0141 (18)0.012 (2)
C130.071 (2)0.058 (2)0.050 (2)0.0072 (17)0.0170 (17)0.0056 (17)
C140.0417 (15)0.0468 (17)0.0373 (15)0.0126 (13)0.0136 (12)0.0019 (13)
C150.0451 (16)0.058 (2)0.0575 (19)0.0149 (14)0.0222 (14)0.0071 (16)
C160.0523 (18)0.0507 (19)0.0534 (19)0.0086 (15)0.0171 (15)0.0070 (15)
C170.0583 (18)0.0483 (18)0.0366 (16)0.0187 (15)0.0089 (14)0.0022 (14)
C180.0544 (18)0.067 (2)0.0487 (18)0.0285 (16)0.0204 (15)0.0026 (16)
C190.0484 (17)0.0560 (19)0.0491 (17)0.0175 (14)0.0215 (14)0.0068 (15)
S20.0445 (4)0.0671 (5)0.0745 (6)0.0002 (4)0.0304 (4)0.0187 (4)
O40.0454 (12)0.0598 (13)0.0554 (12)0.0021 (10)0.0076 (10)0.0059 (10)
O50.109 (2)0.0879 (19)0.0523 (15)0.0279 (16)0.0143 (15)0.0117 (13)
O60.105 (2)0.126 (2)0.0771 (18)0.0361 (18)0.0556 (16)0.0061 (16)
N40.0520 (14)0.0469 (15)0.0442 (14)0.0031 (12)0.0126 (12)0.0044 (12)
N50.0523 (15)0.0680 (19)0.0641 (17)0.0232 (15)0.0161 (13)0.0142 (15)
N60.090 (2)0.0581 (18)0.0512 (18)0.0301 (17)0.0269 (18)0.0066 (14)
C200.0483 (17)0.0461 (17)0.0508 (18)0.0007 (13)0.0182 (14)0.0052 (14)
C210.0444 (16)0.0495 (18)0.0423 (17)0.0029 (14)0.0172 (14)0.0098 (14)
C220.0418 (15)0.0507 (18)0.0411 (16)0.0100 (14)0.0168 (13)0.0082 (14)
C230.0458 (17)0.059 (2)0.0476 (18)0.0087 (15)0.0201 (14)0.0175 (15)
C240.072 (2)0.064 (2)0.062 (2)0.0297 (19)0.0208 (18)0.0054 (18)
C250.067 (2)0.055 (2)0.064 (2)0.0179 (17)0.0284 (17)0.0002 (17)
C260.0504 (17)0.0536 (19)0.0540 (18)0.0098 (15)0.0217 (15)0.0063 (15)
C270.0533 (17)0.0461 (18)0.0500 (19)0.0055 (14)0.0169 (15)0.0009 (15)
C280.093 (3)0.071 (2)0.048 (2)0.016 (2)0.0235 (19)0.0020 (18)
C290.102 (3)0.089 (3)0.055 (2)0.022 (2)0.018 (2)0.014 (2)
C300.072 (2)0.074 (3)0.085 (3)0.013 (2)0.017 (2)0.027 (2)
C310.066 (2)0.058 (2)0.099 (3)0.0140 (18)0.030 (2)0.008 (2)
C320.066 (2)0.054 (2)0.060 (2)0.0117 (17)0.0209 (17)0.0003 (17)
C330.0431 (15)0.0356 (15)0.0492 (17)0.0056 (12)0.0149 (13)0.0013 (13)
C340.0441 (16)0.0520 (18)0.0513 (19)0.0027 (14)0.0152 (14)0.0060 (15)
C350.0551 (19)0.0558 (19)0.058 (2)0.0120 (15)0.0289 (16)0.0057 (16)
C360.0624 (19)0.0414 (17)0.0448 (17)0.0185 (15)0.0194 (15)0.0020 (14)
C370.0518 (18)0.0465 (18)0.0534 (19)0.0116 (14)0.0101 (15)0.0068 (15)
C380.0413 (16)0.0491 (18)0.0584 (19)0.0082 (13)0.0181 (14)0.0063 (15)
S30.0437 (4)0.0639 (5)0.0757 (6)0.0115 (4)0.0240 (4)0.0039 (4)
O70.0379 (11)0.0709 (14)0.0660 (14)0.0219 (10)0.0072 (10)0.0050 (11)
O80.103 (2)0.0682 (17)0.097 (2)0.0031 (16)0.0212 (17)0.0161 (15)
O90.091 (2)0.090 (2)0.165 (3)0.0441 (17)0.024 (2)0.052 (2)
N70.0384 (13)0.0525 (15)0.0515 (15)0.0166 (11)0.0075 (11)0.0059 (12)
N80.079 (2)0.0635 (18)0.0610 (18)0.0200 (15)0.0319 (16)0.0020 (15)
N90.079 (2)0.066 (2)0.0620 (18)0.0295 (18)0.0288 (17)0.0136 (16)
C390.0333 (14)0.0513 (18)0.0602 (19)0.0134 (13)0.0061 (13)0.0056 (15)
C400.0429 (17)0.0461 (17)0.0529 (18)0.0137 (14)0.0108 (14)0.0042 (14)
C410.0462 (16)0.0459 (17)0.0497 (18)0.0166 (14)0.0139 (14)0.0055 (14)
C420.0556 (18)0.0455 (18)0.057 (2)0.0149 (14)0.0217 (15)0.0101 (15)
C430.096 (3)0.068 (2)0.058 (2)0.020 (2)0.028 (2)0.0015 (19)
C440.076 (2)0.060 (2)0.058 (2)0.0113 (18)0.0096 (18)0.0072 (17)
C450.0539 (18)0.0546 (19)0.054 (2)0.0118 (15)0.0107 (16)0.0016 (16)
C460.0377 (15)0.0528 (19)0.062 (2)0.0078 (14)0.0131 (15)0.0095 (16)
C470.069 (2)0.070 (2)0.061 (2)0.0176 (18)0.0110 (18)0.0083 (19)
C480.090 (3)0.104 (3)0.064 (3)0.013 (3)0.018 (2)0.020 (2)
C490.081 (3)0.111 (4)0.095 (3)0.018 (3)0.038 (3)0.042 (3)
C500.066 (2)0.087 (3)0.109 (3)0.031 (2)0.022 (2)0.033 (3)
C510.0478 (18)0.067 (2)0.082 (2)0.0231 (16)0.0138 (17)0.0099 (19)
C520.0354 (15)0.0520 (18)0.0475 (17)0.0168 (13)0.0102 (13)0.0036 (14)
C530.0376 (15)0.057 (2)0.0585 (19)0.0199 (14)0.0130 (14)0.0012 (16)
C540.0429 (16)0.054 (2)0.0564 (19)0.0126 (14)0.0167 (14)0.0034 (15)
C550.0572 (19)0.0515 (19)0.0449 (17)0.0194 (15)0.0195 (15)0.0027 (14)
C560.0469 (18)0.064 (2)0.064 (2)0.0277 (16)0.0099 (15)0.0058 (17)
C570.0362 (15)0.057 (2)0.071 (2)0.0153 (14)0.0106 (15)0.0020 (17)
S40.0411 (4)0.0577 (5)0.0746 (6)0.0084 (4)0.0097 (4)0.0085 (4)
O100.0748 (15)0.0827 (16)0.0578 (13)0.0422 (13)0.0262 (12)0.0025 (12)
O110.095 (2)0.132 (3)0.086 (2)0.011 (2)0.0140 (18)0.0144 (18)
O120.151 (3)0.0831 (19)0.0562 (16)0.0310 (18)0.0192 (18)0.0104 (14)
N100.0553 (14)0.0547 (15)0.0427 (14)0.0257 (12)0.0150 (12)0.0023 (12)
N110.0681 (18)0.0474 (17)0.079 (2)0.0047 (15)0.0136 (15)0.0069 (15)
N120.099 (3)0.0574 (19)0.057 (2)0.0146 (18)0.000 (2)0.0009 (16)
C580.0467 (16)0.0489 (18)0.0529 (18)0.0194 (14)0.0150 (14)0.0003 (14)
C590.0500 (17)0.057 (2)0.0453 (18)0.0219 (15)0.0071 (14)0.0076 (15)
C600.0482 (17)0.0467 (18)0.0445 (17)0.0159 (14)0.0029 (14)0.0086 (14)
C610.0481 (17)0.0453 (18)0.0540 (19)0.0038 (14)0.0010 (15)0.0123 (15)
C620.089 (3)0.049 (2)0.079 (3)0.009 (2)0.014 (2)0.0016 (19)
C630.085 (3)0.052 (2)0.067 (2)0.0310 (19)0.001 (2)0.0010 (18)
C640.0565 (19)0.060 (2)0.0548 (19)0.0230 (16)0.0025 (15)0.0088 (17)
C650.0562 (18)0.056 (2)0.053 (2)0.0225 (16)0.0169 (15)0.0050 (16)
C660.107 (3)0.071 (2)0.050 (2)0.028 (2)0.013 (2)0.0068 (19)
C670.119 (3)0.104 (4)0.054 (2)0.036 (3)0.020 (2)0.019 (2)
C680.076 (3)0.098 (3)0.091 (3)0.039 (2)0.042 (2)0.042 (3)
C690.060 (2)0.065 (2)0.111 (3)0.0186 (18)0.043 (2)0.021 (2)
C700.0555 (19)0.063 (2)0.068 (2)0.0200 (16)0.0230 (16)0.0060 (19)
C710.0457 (16)0.0379 (16)0.0438 (16)0.0113 (13)0.0130 (13)0.0001 (13)
C720.0460 (17)0.059 (2)0.061 (2)0.0135 (15)0.0183 (15)0.0031 (16)
C730.0456 (17)0.063 (2)0.062 (2)0.0090 (15)0.0032 (16)0.0036 (17)
C740.073 (2)0.0427 (18)0.0426 (18)0.0097 (16)0.0075 (17)0.0001 (14)
C750.080 (2)0.0490 (19)0.054 (2)0.0126 (17)0.0315 (18)0.0025 (16)
C760.0500 (17)0.0489 (18)0.059 (2)0.0121 (14)0.0234 (16)0.0039 (15)
O130.115 (2)0.112 (2)0.0486 (15)0.0127 (17)0.0069 (14)0.0010 (14)
C770.176 (6)0.156 (5)0.090 (3)0.079 (4)0.044 (4)0.007 (3)
C790.117 (4)0.116 (4)0.071 (3)0.037 (3)0.033 (3)0.024 (3)
O140.079 (7)0.128 (9)0.085 (8)0.016 (7)0.032 (6)0.024 (7)
C78A0.082 (7)0.096 (8)0.050 (4)0.024 (6)0.017 (5)0.000 (4)
C78B0.074 (9)0.085 (8)0.049 (6)0.010 (7)0.003 (6)0.003 (5)
Geometric parameters (Å, º) top
S1—C11.821 (3)C39—C521.521 (4)
S1—C41.737 (3)C40—C411.493 (4)
O1—C21.221 (3)C41—C421.397 (4)
O2—N31.209 (3)C41—C451.382 (4)
O3—N31.209 (3)C43—H430.9300
N1—C11.466 (3)C43—C441.369 (5)
N1—C21.369 (3)C44—H440.9300
N1—C81.434 (3)C44—C451.371 (4)
N2—C41.346 (3)C45—H450.9300
N2—C51.327 (4)C46—C471.376 (4)
N3—C171.475 (4)C46—C511.378 (4)
C1—H10.9800C47—H470.9300
C1—C141.511 (4)C47—C481.383 (5)
C2—C31.492 (4)C48—H480.9300
C3—C41.392 (3)C48—C491.382 (5)
C3—C71.389 (4)C49—H490.9300
C5—H50.9300C49—C501.369 (5)
C5—C61.374 (4)C50—H500.9300
C6—H60.9300C50—C511.376 (5)
C6—C71.378 (4)C51—H510.9300
C7—H70.9300C52—C531.385 (4)
C8—C91.382 (4)C52—C571.388 (4)
C8—C131.387 (4)C53—H530.9300
C9—H90.9300C53—C541.381 (4)
C9—C101.378 (4)C54—H540.9300
C10—H100.9300C54—C551.358 (4)
C10—C111.374 (5)C55—C561.384 (4)
C11—H110.9300C56—H560.9300
C11—C121.377 (5)C56—C571.369 (4)
C12—H120.9300C57—H570.9300
C12—C131.382 (4)S4—C581.821 (3)
C13—H130.9300S4—C611.746 (3)
C14—C151.390 (3)O10—C591.220 (3)
C14—C191.385 (4)O11—N121.207 (4)
C15—H150.9300O12—N121.217 (4)
C15—C161.369 (4)N10—C581.461 (3)
C16—H160.9300N10—C591.367 (3)
C16—C171.369 (4)N10—C651.443 (4)
C17—C181.366 (4)N11—C611.332 (4)
C18—H180.9300N11—C621.327 (4)
C18—C191.382 (4)N12—C741.475 (4)
C19—H190.9300C58—H580.9800
S2—C201.821 (3)C58—C711.518 (4)
S2—C231.742 (3)C59—C601.486 (4)
O4—C211.219 (3)C60—C611.392 (4)
O5—N61.214 (3)C60—C641.385 (4)
O6—N61.211 (3)C62—H620.9300
N4—C201.462 (3)C62—C631.365 (5)
N4—C211.364 (3)C63—H630.9300
N4—C271.432 (4)C63—C641.382 (4)
N5—C231.335 (4)C64—H640.9300
N5—C241.332 (4)C65—C661.378 (4)
N6—C361.484 (4)C65—C701.373 (4)
C20—H200.9800C66—H660.9300
C20—C331.517 (4)C66—C671.377 (5)
C21—C221.485 (4)C67—H670.9300
C22—C231.400 (4)C67—C681.372 (5)
C22—C261.390 (4)C68—H680.9300
C24—H240.9300C68—C691.354 (5)
C24—C251.370 (4)C69—H690.9300
C25—H250.9300C69—C701.385 (4)
C25—C261.373 (4)C70—H700.9300
C26—H260.9300C71—C721.382 (4)
C27—C281.381 (4)C71—C761.388 (4)
C27—C321.382 (4)C72—H720.9300
C28—H280.9300C72—C731.380 (4)
C28—C291.380 (5)C73—H730.9300
C29—H290.9300C73—C741.365 (4)
C29—C301.368 (5)C74—C751.375 (4)
C30—H300.9300C75—H750.9300
C30—C311.366 (5)C75—C761.367 (4)
C31—H310.9300C76—H760.9300
C31—C321.382 (4)O13—H13A0.8200
C32—H320.9300O13—H13B0.8200
C33—C341.385 (3)O13—C78A1.422 (8)
C33—C381.393 (4)O13—C78B1.564 (14)
C34—H340.9300C77—H77A0.9600
C34—C351.378 (4)C77—H77B0.9600
C35—H350.9300C77—H77C0.9600
C35—C361.372 (4)C77—H77D0.9600
C36—C371.367 (4)C77—H77E0.9600
C37—H370.9300C77—H77F0.9600
C37—C381.371 (4)C77—C78A1.409 (11)
C38—H380.9300C77—C78B1.512 (17)
S3—C391.816 (3)C79—H79A0.9600
S3—C421.744 (3)C79—H79B0.9600
O7—C401.225 (3)C79—H79C0.9600
O8—N91.209 (3)C79—H79D0.9600
O9—N91.207 (3)C79—H79E0.9600
N7—C391.464 (3)C79—H79F0.9600
N7—C401.370 (3)C79—C78A1.496 (10)
N7—C461.441 (4)C79—C78B1.371 (13)
N8—C421.338 (4)O14—H14A0.8499
N8—C431.331 (4)O14—H14B0.8501
N9—C551.468 (4)C78A—H78A0.9800
C39—H390.9800C78B—H78B0.9800
C4—S1—C197.70 (12)N8—C42—S3114.8 (2)
C2—N1—C1122.3 (2)N8—C42—C41123.8 (3)
C2—N1—C8119.9 (2)C41—C42—S3121.4 (2)
C8—N1—C1117.4 (2)N8—C43—H43117.8
C5—N2—C4117.3 (2)N8—C43—C44124.3 (3)
O2—N3—C17118.0 (3)C44—C43—H43117.8
O3—N3—O2123.6 (3)C43—C44—H44120.5
O3—N3—C17118.4 (3)C43—C44—C45119.0 (3)
S1—C1—H1105.8C45—C44—H44120.5
N1—C1—S1112.14 (18)C41—C45—H45120.6
N1—C1—H1105.8C44—C45—C41118.9 (3)
N1—C1—C14115.6 (2)C44—C45—H45120.6
C14—C1—S1110.95 (18)C47—C46—N7119.8 (3)
C14—C1—H1105.8C47—C46—C51120.4 (3)
O1—C2—N1122.1 (2)C51—C46—N7119.8 (3)
O1—C2—C3120.1 (2)C46—C47—H47120.3
N1—C2—C3117.8 (2)C46—C47—C48119.4 (4)
C4—C3—C2124.1 (2)C48—C47—H47120.3
C7—C3—C2117.8 (2)C47—C48—H48119.8
C7—C3—C4117.7 (3)C49—C48—C47120.3 (4)
N2—C4—S1115.1 (2)C49—C48—H48119.8
N2—C4—C3123.2 (3)C48—C49—H49120.2
C3—C4—S1121.7 (2)C50—C49—C48119.6 (4)
N2—C5—H5118.1C50—C49—H49120.2
N2—C5—C6123.9 (3)C49—C50—H50119.7
C6—C5—H5118.1C49—C50—C51120.6 (4)
C5—C6—H6120.7C51—C50—H50119.7
C5—C6—C7118.7 (3)C46—C51—H51120.2
C7—C6—H6120.7C50—C51—C46119.7 (3)
C3—C7—H7120.4C50—C51—H51120.2
C6—C7—C3119.2 (3)C53—C52—C39122.3 (2)
C6—C7—H7120.4C53—C52—C57118.5 (3)
C9—C8—N1120.9 (3)C57—C52—C39119.2 (2)
C9—C8—C13119.3 (3)C52—C53—H53119.7
C13—C8—N1119.8 (3)C54—C53—C52120.6 (3)
C8—C9—H9119.9C54—C53—H53119.7
C10—C9—C8120.2 (3)C53—C54—H54120.4
C10—C9—H9119.9C55—C54—C53119.2 (3)
C9—C10—H10119.8C55—C54—H54120.4
C11—C10—C9120.4 (3)C54—C55—N9118.1 (3)
C11—C10—H10119.8C54—C55—C56122.0 (3)
C10—C11—H11120.1C56—C55—N9119.8 (3)
C10—C11—C12119.8 (3)C55—C56—H56121.0
C12—C11—H11120.1C57—C56—C55118.1 (3)
C11—C12—H12119.9C57—C56—H56121.0
C11—C12—C13120.2 (3)C52—C57—H57119.2
C13—C12—H12119.9C56—C57—C52121.6 (3)
C8—C13—H13120.0C56—C57—H57119.2
C12—C13—C8120.1 (3)C61—S4—C5897.01 (14)
C12—C13—H13120.0C59—N10—C58122.4 (2)
C15—C14—C1118.0 (2)C59—N10—C65119.7 (2)
C19—C14—C1123.5 (2)C65—N10—C58117.8 (2)
C19—C14—C15118.5 (3)C62—N11—C61116.9 (3)
C14—C15—H15119.3O11—N12—O12124.0 (3)
C16—C15—C14121.5 (3)O11—N12—C74117.6 (4)
C16—C15—H15119.3O12—N12—C74118.3 (4)
C15—C16—H16120.8S4—C58—H58106.5
C17—C16—C15118.5 (3)N10—C58—S4111.63 (19)
C17—C16—H16120.8N10—C58—H58106.5
C16—C17—N3118.7 (3)N10—C58—C71114.8 (2)
C18—C17—N3119.3 (3)C71—C58—S4110.50 (18)
C18—C17—C16122.0 (3)C71—C58—H58106.5
C17—C18—H18120.4O10—C59—N10121.8 (3)
C17—C18—C19119.2 (3)O10—C59—C60120.9 (3)
C19—C18—H18120.4N10—C59—C60117.2 (3)
C14—C19—H19119.8C61—C60—C59124.3 (3)
C18—C19—C14120.4 (3)C64—C60—C59118.1 (3)
C18—C19—H19119.8C64—C60—C61117.2 (3)
C23—S2—C2097.49 (13)N11—C61—S4114.7 (2)
C21—N4—C20121.7 (2)N11—C61—C60123.8 (3)
C21—N4—C27119.5 (2)C60—C61—S4121.4 (2)
C27—N4—C20118.6 (2)N11—C62—H62117.9
C24—N5—C23117.0 (3)N11—C62—C63124.3 (3)
O5—N6—C36118.2 (3)C63—C62—H62117.9
O6—N6—O5124.1 (3)C62—C63—H63120.9
O6—N6—C36117.7 (3)C62—C63—C64118.2 (3)
S2—C20—H20105.9C64—C63—H63120.9
N4—C20—S2112.10 (19)C60—C64—H64120.3
N4—C20—H20105.9C63—C64—C60119.4 (3)
N4—C20—C33115.2 (2)C63—C64—H64120.3
C33—C20—S2111.0 (2)C66—C65—N10119.1 (3)
C33—C20—H20105.9C70—C65—N10120.2 (3)
O4—C21—N4121.1 (3)C70—C65—C66120.7 (3)
O4—C21—C22120.7 (2)C65—C66—H66120.4
N4—C21—C22118.2 (2)C67—C66—C65119.3 (4)
C23—C22—C21123.7 (3)C67—C66—H66120.4
C26—C22—C21119.2 (2)C66—C67—H67119.9
C26—C22—C23116.7 (3)C68—C67—C66120.2 (4)
N5—C23—S2114.6 (2)C68—C67—H67119.9
N5—C23—C22123.7 (3)C67—C68—H68119.9
C22—C23—S2121.6 (2)C69—C68—C67120.2 (4)
N5—C24—H24118.0C69—C68—H68119.9
N5—C24—C25124.0 (3)C68—C69—H69119.6
C25—C24—H24118.0C68—C69—C70120.8 (4)
C24—C25—H25120.8C70—C69—H69119.6
C24—C25—C26118.3 (3)C65—C70—C69118.9 (3)
C26—C25—H25120.8C65—C70—H70120.6
C22—C26—H26120.0C69—C70—H70120.6
C25—C26—C22120.0 (3)C72—C71—C58123.0 (2)
C25—C26—H26120.0C72—C71—C76118.4 (3)
C28—C27—N4119.6 (3)C76—C71—C58118.6 (2)
C28—C27—C32119.9 (3)C71—C72—H72119.5
C32—C27—N4120.5 (3)C73—C72—C71120.9 (3)
C27—C28—H28120.3C73—C72—H72119.5
C29—C28—C27119.4 (4)C72—C73—H73120.6
C29—C28—H28120.3C74—C73—C72118.9 (3)
C28—C29—H29119.7C74—C73—H73120.6
C30—C29—C28120.6 (4)C73—C74—N12119.8 (3)
C30—C29—H29119.7C73—C74—C75121.8 (3)
C29—C30—H30119.9C75—C74—N12118.4 (3)
C31—C30—C29120.2 (4)C74—C75—H75120.6
C31—C30—H30119.9C76—C75—C74118.7 (3)
C30—C31—H31119.9C76—C75—H75120.6
C30—C31—C32120.1 (4)C71—C76—H76119.3
C32—C31—H31119.9C75—C76—C71121.3 (3)
C27—C32—H32120.1C75—C76—H76119.3
C31—C32—C27119.8 (3)C78A—O13—H13A109.5
C31—C32—H32120.1C78B—O13—H13B109.5
C34—C33—C20123.3 (2)H77A—C77—H77B109.5
C34—C33—C38118.5 (3)H77A—C77—H77C109.5
C38—C33—C20118.2 (2)H77B—C77—H77C109.5
C33—C34—H34119.6H77D—C77—H77E109.5
C35—C34—C33120.9 (3)H77D—C77—H77F109.5
C35—C34—H34119.6H77E—C77—H77F109.5
C34—C35—H35120.7C78A—C77—H77A109.5
C36—C35—C34118.6 (3)C78A—C77—H77B109.5
C36—C35—H35120.7C78A—C77—H77C109.5
C35—C36—N6119.6 (3)C78B—C77—H77D109.5
C37—C36—N6118.2 (3)C78B—C77—H77E109.5
C37—C36—C35122.2 (3)C78B—C77—H77F109.5
C36—C37—H37120.6H79A—C79—H79B109.5
C36—C37—C38118.8 (3)H79A—C79—H79C109.5
C38—C37—H37120.6H79B—C79—H79C109.5
C33—C38—H38119.5H79D—C79—H79E109.5
C37—C38—C33121.0 (3)H79D—C79—H79F109.5
C37—C38—H38119.5H79E—C79—H79F109.5
C42—S3—C3997.62 (13)C78A—C79—H79A109.5
C40—N7—C39121.1 (2)C78A—C79—H79B109.5
C40—N7—C46120.7 (2)C78A—C79—H79C109.5
C46—N7—C39117.3 (2)C78B—C79—H79D109.5
C43—N8—C42116.2 (3)C78B—C79—H79E109.5
O8—N9—C55118.8 (3)C78B—C79—H79F109.5
O9—N9—O8122.5 (3)H14A—O14—H14B109.5
O9—N9—C55118.7 (3)O13—C78A—C79110.4 (7)
S3—C39—H39106.1O13—C78A—H78A103.9
N7—C39—S3112.11 (19)C77—C78A—O13114.2 (8)
N7—C39—H39106.1C77—C78A—C79118.5 (9)
N7—C39—C52114.1 (2)C77—C78A—H78A103.9
C52—C39—S3111.63 (19)C79—C78A—H78A103.9
C52—C39—H39106.1O13—C78B—H78B108.6
O7—C40—N7122.3 (3)C77—C78B—O13101.2 (12)
O7—C40—C41119.4 (3)C77—C78B—H78B108.6
N7—C40—C41118.3 (2)C79—C78B—O13109.3 (9)
C42—C41—C40123.9 (3)C79—C78B—C77119.9 (10)
C45—C41—C40118.2 (3)C79—C78B—H78B108.6
C45—C41—C42117.7 (3)
S1—C1—C14—C1568.1 (3)S3—C39—C52—C53108.1 (3)
S1—C1—C14—C19114.3 (3)S3—C39—C52—C5772.3 (3)
O1—C2—C3—C4157.9 (3)O7—C40—C41—C42159.3 (3)
O1—C2—C3—C715.1 (4)O7—C40—C41—C4514.5 (4)
O2—N3—C17—C16163.6 (3)O8—N9—C55—C549.4 (4)
O2—N3—C17—C1817.5 (4)O8—N9—C55—C56169.0 (3)
O3—N3—C17—C1615.8 (4)O9—N9—C55—C54171.6 (3)
O3—N3—C17—C18163.1 (3)O9—N9—C55—C5610.1 (4)
N1—C1—C14—C15162.7 (2)N7—C39—C52—C5320.3 (4)
N1—C1—C14—C1914.9 (4)N7—C39—C52—C57159.4 (3)
N1—C2—C3—C420.3 (4)N7—C40—C41—C4219.5 (4)
N1—C2—C3—C7166.7 (2)N7—C40—C41—C45166.7 (2)
N1—C8—C9—C10179.1 (2)N7—C46—C47—C48179.3 (3)
N1—C8—C13—C12178.5 (3)N7—C46—C51—C50179.4 (3)
N2—C5—C6—C73.0 (5)N8—C43—C44—C453.7 (5)
N3—C17—C18—C19178.1 (2)N9—C55—C56—C57178.5 (3)
C1—S1—C4—N2156.8 (2)C39—S3—C42—N8157.9 (2)
C1—S1—C4—C326.2 (2)C39—S3—C42—C4125.0 (3)
C1—N1—C2—O1170.8 (2)C39—N7—C40—O7167.4 (3)
C1—N1—C2—C311.1 (4)C39—N7—C40—C4113.8 (4)
C1—N1—C8—C9134.7 (3)C39—N7—C46—C4736.5 (4)
C1—N1—C8—C1343.3 (3)C39—N7—C46—C51142.6 (3)
C1—C14—C15—C16177.7 (2)C39—C52—C53—C54179.7 (3)
C1—C14—C19—C18178.3 (2)C39—C52—C57—C56179.5 (3)
C2—N1—C1—S149.1 (3)C40—N7—C39—S352.1 (3)
C2—N1—C1—C1479.4 (3)C40—N7—C39—C5276.0 (3)
C2—N1—C8—C952.5 (3)C40—N7—C46—C47132.7 (3)
C2—N1—C8—C13129.5 (3)C40—N7—C46—C5148.2 (4)
C2—C3—C4—S16.5 (4)C40—C41—C42—S37.8 (4)
C2—C3—C4—N2170.2 (2)C40—C41—C42—N8169.0 (3)
C2—C3—C7—C6171.8 (3)C40—C41—C45—C44171.5 (3)
C4—S1—C1—N150.9 (2)C42—S3—C39—N752.0 (2)
C4—S1—C1—C1480.10 (19)C42—S3—C39—C5277.5 (2)
C4—N2—C5—C61.9 (4)C42—N8—C43—C441.7 (5)
C4—C3—C7—C61.7 (4)C42—C41—C45—C442.7 (4)
C5—N2—C4—S1178.0 (2)C43—N8—C42—S3179.6 (2)
C5—N2—C4—C31.1 (4)C43—N8—C42—C412.7 (4)
C5—C6—C7—C31.0 (4)C43—C44—C45—C411.2 (5)
C7—C3—C4—S1179.6 (2)C45—C41—C42—S3178.4 (2)
C7—C3—C4—N22.9 (4)C45—C41—C42—N84.9 (4)
C8—N1—C1—S1138.2 (2)C46—N7—C39—S3138.7 (2)
C8—N1—C1—C1493.2 (3)C46—N7—C39—C5293.1 (3)
C8—N1—C2—O11.7 (4)C46—N7—C40—O71.4 (4)
C8—N1—C2—C3176.5 (2)C46—N7—C40—C41177.4 (2)
C8—C9—C10—C111.0 (4)C46—C47—C48—C491.4 (5)
C9—C8—C13—C120.5 (4)C47—C46—C51—C501.5 (4)
C9—C10—C11—C120.2 (5)C47—C48—C49—C501.7 (6)
C10—C11—C12—C130.5 (5)C48—C49—C50—C510.5 (6)
C11—C12—C13—C80.4 (5)C49—C50—C51—C461.1 (5)
C13—C8—C9—C101.2 (4)C51—C46—C47—C480.2 (5)
C14—C15—C16—C170.3 (4)C52—C53—C54—C551.2 (4)
C15—C14—C19—C180.7 (4)C53—C52—C57—C560.2 (4)
C15—C16—C17—N3178.8 (2)C53—C54—C55—N9179.3 (2)
C15—C16—C17—C180.1 (4)C53—C54—C55—C561.0 (4)
C16—C17—C18—C190.7 (4)C54—C55—C56—C570.2 (4)
C17—C18—C19—C141.1 (4)C55—C56—C57—C520.4 (4)
C19—C14—C15—C160.0 (4)C57—C52—C53—C540.7 (4)
S2—C20—C33—C34123.0 (3)S4—C58—C71—C72124.5 (2)
S2—C20—C33—C3857.6 (3)S4—C58—C71—C7657.2 (3)
O4—C21—C22—C23157.5 (3)O10—C59—C60—C61156.1 (3)
O4—C21—C22—C2615.0 (4)O10—C59—C60—C6416.3 (4)
O5—N6—C36—C35173.3 (3)O11—N12—C74—C736.5 (5)
O5—N6—C36—C378.4 (4)O11—N12—C74—C75171.6 (3)
O6—N6—C36—C356.9 (4)O12—N12—C74—C73173.4 (3)
O6—N6—C36—C37171.5 (3)O12—N12—C74—C758.6 (4)
N4—C20—C33—C345.7 (4)N10—C58—C71—C722.8 (4)
N4—C20—C33—C38173.7 (2)N10—C58—C71—C76175.5 (2)
N4—C21—C22—C2320.9 (4)N10—C59—C60—C6121.7 (4)
N4—C21—C22—C26166.6 (2)N10—C59—C60—C64165.9 (2)
N4—C27—C28—C29179.8 (3)N10—C65—C66—C67178.4 (3)
N4—C27—C32—C31179.2 (3)N10—C65—C70—C69178.0 (3)
N5—C24—C25—C264.6 (5)N11—C62—C63—C644.4 (5)
N6—C36—C37—C38176.7 (2)N12—C74—C75—C76177.7 (3)
C20—S2—C23—N5158.5 (2)C58—S4—C61—N11156.2 (2)
C20—S2—C23—C2224.2 (2)C58—S4—C61—C6026.0 (3)
C20—N4—C21—O4168.9 (2)C58—N10—C59—O10170.6 (3)
C20—N4—C21—C2212.7 (4)C58—N10—C59—C6011.6 (4)
C20—N4—C27—C28122.6 (3)C58—N10—C65—C66119.8 (3)
C20—N4—C27—C3256.4 (3)C58—N10—C65—C7058.7 (4)
C20—C33—C34—C35177.5 (3)C58—C71—C72—C73178.1 (3)
C20—C33—C38—C37177.9 (3)C58—C71—C76—C75178.6 (3)
C21—N4—C20—S251.3 (3)C59—N10—C58—S451.2 (3)
C21—N4—C20—C3376.9 (3)C59—N10—C58—C7175.6 (3)
C21—N4—C27—C2862.0 (4)C59—N10—C65—C6663.2 (4)
C21—N4—C27—C32119.1 (3)C59—N10—C65—C70118.4 (3)
C21—C22—C23—S29.0 (4)C59—C60—C61—S48.1 (4)
C21—C22—C23—N5168.0 (3)C59—C60—C61—N11169.4 (3)
C21—C22—C26—C25171.3 (2)C59—C60—C64—C63172.3 (3)
C23—S2—C20—N451.1 (2)C61—S4—C58—N1052.1 (2)
C23—S2—C20—C3379.2 (2)C61—S4—C58—C7176.9 (2)
C23—N5—C24—C251.9 (4)C61—N11—C62—C632.2 (5)
C23—C22—C26—C251.7 (4)C61—C60—C64—C630.7 (4)
C24—N5—C23—S2179.9 (2)C62—N11—C61—S4179.4 (2)
C24—N5—C23—C222.9 (4)C62—N11—C61—C601.7 (4)
C24—C25—C26—C222.6 (4)C62—C63—C64—C602.8 (5)
C26—C22—C23—S2178.3 (2)C64—C60—C61—S4179.4 (2)
C26—C22—C23—N54.6 (4)C64—C60—C61—N113.1 (4)
C27—N4—C20—S2133.4 (2)C65—N10—C58—S4131.9 (2)
C27—N4—C20—C3398.5 (3)C65—N10—C58—C71101.4 (3)
C27—N4—C21—O46.4 (4)C65—N10—C59—O106.3 (4)
C27—N4—C21—C22172.0 (2)C65—N10—C59—C60171.5 (2)
C27—C28—C29—C300.9 (5)C65—C66—C67—C680.8 (6)
C28—C27—C32—C310.3 (4)C66—C65—C70—C690.4 (5)
C28—C29—C30—C310.4 (6)C66—C67—C68—C691.3 (6)
C29—C30—C31—C320.1 (5)C67—C68—C69—C700.9 (5)
C30—C31—C32—C270.2 (5)C68—C69—C70—C650.1 (5)
C32—C27—C28—C290.9 (5)C70—C65—C66—C670.0 (5)
C33—C34—C35—C360.5 (4)C71—C72—C73—C740.3 (4)
C34—C33—C38—C371.5 (4)C72—C71—C76—C750.3 (4)
C34—C35—C36—N6177.0 (2)C72—C73—C74—N12178.1 (3)
C34—C35—C36—C371.3 (4)C72—C73—C74—C750.1 (5)
C35—C36—C37—C381.7 (4)C73—C74—C75—C760.3 (5)
C36—C37—C38—C330.2 (4)C74—C75—C76—C710.5 (4)
C38—C33—C34—C351.9 (4)C76—C71—C72—C730.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O130.982.493.461 (4)172
C6—H6···N5i0.932.743.431 (4)132
C39—H39···O14ii0.982.413.339 (10)158
C44—H44···N11iii0.932.773.479 (4)134
C48—H48···O140.932.293.065 (12)141
C50—H50···O2iv0.932.623.412 (5)144
C58—H58···O7v0.982.493.246 (3)134
C76—H76···O7v0.932.783.498 (4)135
C79—H79A···O9ii0.962.573.353 (6)138
C79—H79E···O8vi0.962.613.455 (5)147
C79—H79F···O2iv0.962.753.493 (6)135
O13—H13B···O4vii0.821.952.766 (3)176
Symmetry codes: (i) x, y, z1; (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, y1, 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.

References

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