Syntheses of PDE3A inhibitor ORG9935 and determination of the absolute stereochemistries of its enantiomers by X-ray crystallography
Jakkaraj, Sudhakar R.; Young, Victor G.; Georg, Gunda I.; Tetrahedron 74 (2018) 2769–2774; doi:10.1016/j.tet.2018.04.045

data_1566136
_publ_section_title
;
 Syntheses of PDE3A inhibitor ORG9935 and determination of the absolute
 stereochemistries of its enantiomers by X-ray crystallography
;
_journal_issue                   22
_journal_name_full               Tetrahedron
_journal_page_first              2769
_journal_page_last               2774
_journal_paper_doi               10.1016/j.tet.2018.04.045
_journal_volume                  74
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H16 N2 O3 S'
_chemical_formula_sum            'C15 H16 N2 O3 S'
_chemical_formula_weight         304.36
_chemical_name_common            17217z
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                88.856(2)
_cell_angle_beta                 87.710(3)
_cell_angle_gamma                60.02
_cell_formula_units_Z            24
_cell_length_a                   14.9664(16)
_cell_length_b                   14.9764(15)
_cell_length_c                   47.378(4)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.33
_cell_volume                     9191.2(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-AXS VENTURE PHOTON-II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            194714
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.290
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-261/2 (Sheldrick, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       Plate
_exptl_crystal_F_000             3840
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.8620
_exptl_transmission_factor_min   0.5976
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 26459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     4538
_refine_ls_number_reflns         74852
_refine_ls_number_restraints     4035
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0873
_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^)+(0.1416P)^2^+13.2947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2410
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                64924
_reflns_number_total             74852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Tetrahedron-2018-74-2769.cif
_cod_data_source_block           17217z
_cod_original_cell_volume        9191.5(15)
_cod_database_code               1566136
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014/6