Crystal structure, Hirshfeld analysis and a molecular docking study of a new inhibitor of the Hepatitis B virus (HBV): ethyl 5-methyl-1,1-dioxo-2-{[5-(pentan-3-yl)-1,2,4-oxadiazol-3-yl]methyl}-2<i>H</i>-1,2,6-thiadiazine-4-carboxylate
Ivachtchenko, Alexandre V.; Kovalenko, Sergiy M.; Kravchenko, Dmitry V.; Mitkin, Oleg D.; Ivanov, Vladimir V.; Langer, Thierry; Acta Crystallographica Section E 76 (2020) 12–17; doi:10.1107/S2056989019015986

data_2243233
_publ_section_title
;
 Crystal structure, Hirshfeld analysis and a molecular docking study of a
 new inhibitor of the Hepatitis B virus (HBV): ethyl
 5-methyl-1,1-dioxo-2-{[5-(pentan-3-yl)-1,2,4-oxadiazol-3-yl]methyl}-2<i>H</i>-1,2,6-thiadiazine-4-carboxylate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              12
_journal_page_last               17
_journal_paper_doi               10.1107/S2056989019015986
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H22 N4 O5 S'
_chemical_formula_moiety         'C15 H22 N4 O5 S'
_chemical_formula_sum            'C15 H22 N4 O5 S'
_chemical_formula_weight         370.42
_chemical_name_systematic
'Ethyl 5-methyl-1,1-dioxo-2-{[5-(pentan-3-yl)-1,2,4-oxadiazol-3-yl]methyl}-2<i>H</i>-1,2,6-thiadiazine-4-carboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4962(5)
_cell_length_b                   9.9237(4)
_cell_length_c                   29.5925(15)
_cell_measurement_reflns_used    3271
_cell_measurement_temperature    293.20
_cell_measurement_theta_max      23.2650
_cell_measurement_theta_min      3.5460
_cell_volume                     3669.7(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009) and Mercury (Macrae <i>et
al.</i>,  2008)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009), SHELXL (Sheldrick,
2015b),
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26547
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.961
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+1.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                2510
_reflns_number_total             3211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5529sup1.cif
_cod_data_source_block           I
_cod_database_code               2243233
_cod_database_fobs_code          2243233
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.979