Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation
Wu, Yingtao; Guan, Xin; Jiao, Kehan; Zhao, Huaqiu; Li, Mingrui; Sun, Jiaqiong; Zheng, Guangfan; Zhang, Qian; Green Chemistry 26 (2024) 10940–10949; doi:10.1039/D4GC03113J

data_7249409
_publ_section_title
;
 Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative
 amidation
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              10940
_journal_page_last               10949
_journal_paper_doi               10.1039/D4GC03113J
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C27 H19 Br N2 O2 S'
_chemical_formula_sum            'C27 H19 Br N2 O2 S'
_chemical_formula_weight         515.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-12-02 deposited with the CCDC.	2024-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2241(8)
_cell_length_b                   10.3990(10)
_cell_length_c                   25.056(2)
_cell_measurement_reflns_used    9213
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      64.417
_cell_measurement_theta_min      3.528
_cell_volume                     2403.4(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      287.16
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9599
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        63.862
_diffrn_reflns_theta_max         63.862
_diffrn_reflns_theta_min         3.528
_exptl_absorpt_coefficient_mu    3.356
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.578
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.092(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0604P)^2^+1.7858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                3609
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc03113j2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
         Adding full bibliography for 7249409.cif.

2025-04-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H38 Br2 N4 O4 S2'
_cod_original_formula_weight         1030.82
_cod_original_formula_moiety         '2(C27 H19 Br N2 O2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7249409
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.488
_shelx_estimated_absorpt_t_min   0.433
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N003(H003), N006(H006)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
;
_shelx_res_checksum              53306
_olex2_submission_special_instructions 'No special instructions were received'