Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles.
Formica, Michele; Sorin, Geoffroy; Farley, Alistair J. M.; Díaz, Jesús; Paton, Robert S.; Dixon, Darren J.; Chemical science 9 (2018) 6969–6974; doi:10.1039/c8sc01804a

data_1549716
_publ_section_title
;
 Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael
 addition of alkyl thiols to alkenyl benzimidazoles.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              6969
_journal_page_last               6974
_journal_paper_doi               10.1039/c8sc01804a
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18 N2 S1'
_chemical_formula_sum            'C13 H18 N2 S'
_chemical_formula_weight         234.37
_chemical_melting_point          ?
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-21
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_audit_update_record
;
2018-03-28 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7206(4)
_cell_length_b                   9.8606(2)
_cell_length_c                   6.34860(10)
_cell_measurement_reflns_used    14563
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1297.13(4)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            26964
_diffrn_reflns_theta_full        76.118
_diffrn_reflns_theta_max         76.118
_diffrn_reflns_theta_min         4.267
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details 'Flack (1983), 1104 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.0015972
_refine_ls_shift/su_mean         0.0000393
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.48P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1075
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1075
_reflns_limit_h_max              25
_reflns_limit_h_min              -25
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                2630
_reflns_number_total             2686
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0378
_oxford_refine_ls_scale          8.6(3)
_oxford_reflns_number_all        2686
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 014djd16
_cod_data_source_file            c8sc01804a2.cif
_cod_data_source_block           25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549716.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 2 '
_cod_original_formula_sum        'C13 H18 N2 S1'
_cod_database_code               1549716