Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation.
Tian, Ting; Dong, An-Shun; Chen, Dan; Cao, Xian-Ting; Wang, Guannan; Organic & biomolecular chemistry 17 (2019) 7664–7668; doi:10.1039/c9ob01539f

data_7156996
_publ_section_title
;
 Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides
 through iridium-catalyzed C-H activation.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7664
_journal_page_last               7668
_journal_paper_doi               10.1039/c9ob01539f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C20 H18 N2 O4 S'
_chemical_formula_sum            'C20 H18 N2 O4 S'
_chemical_formula_weight         382.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-05-14 deposited with the CCDC.    2019-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                113.249(4)
_cell_angle_beta                 91.355(4)
_cell_angle_gamma                107.746(3)
_cell_formula_units_Z            2
_cell_length_a                   9.231(3)
_cell_length_b                   9.999(3)
_cell_length_c                   11.902(4)
_cell_measurement_reflns_used    3131
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.723
_cell_measurement_theta_min      2.317
_cell_volume                     948.2(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7500
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         2.349
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0507 before and 0.0307 after correction. The Ratio of minimum to maximum transmission is 0.8471. The \l/2 correction factor is 0.00150.'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0532P)^2^+0.2953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2992
_reflns_number_total             4036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01539f2.cif
_cod_data_source_block           180511cxj_0m
_cod_depositor_comments          'Adding full bibliography for 7156996.cif.'
_cod_database_code               7156996
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C4(H4), C20(H20), C19(H19), C8(H8), C6(H6), C18(H18), C5(H5), C7(H7)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              76582
_shelx_hkl_checksum              35185
_olex2_submission_special_instructions 'No special instructions were received'