Enantioselective Synthesis of γ-Phenyl-γ-amino Vinyl Phosphonates and Sulfones and Their Application to the Synthesis of Novel Highly Potent Antimalarials.
Aratikatla, Eswar K.; Kalamuddin, Md; Malhotra, Pawan; Mohmmed, Asif; Bhattacharya, Asish K.; ACS omega 5 (2020) 29025–29037; doi:10.1021/acsomega.0c03470

data_4518196
_publ_section_title
;
 Enantioselective Synthesis of \g-Phenyl-\g-amino Vinyl Phosphonates and
 Sulfones and Their Application to the Synthesis of Novel Highly Potent
 Antimalarials.
;
_journal_issue                   45
_journal_name_full               'ACS omega'
_journal_page_first              29025
_journal_page_last               29037
_journal_paper_doi               10.1021/acsomega.0c03470
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C34 H29 N O2 S'
_chemical_formula_sum            'C34 H29 N O2 S'
_chemical_formula_weight         515.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3426(4)
_cell_length_b                   32.7061(8)
_cell_length_c                   10.0263(2)
_cell_measurement_reflns_used    9705
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.19
_cell_measurement_theta_min      3.82
_cell_volume                     5359.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            41477
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_min         3.023
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 4437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         10502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+1.3964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                10201
_reflns_number_total             10502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c03470_si_002.cif
_cod_data_source_block           EKA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4518196.cif.
;
_cod_database_code               4518196
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.788
_shelx_estimated_absorpt_t_max   0.913
_shelx_res_checksum              15472
_shelx_hkl_checksum              43622