Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water
Chakrabarti, Kaushik; Maji, Milan; Kundu, Sabuj; Green Chemistry 21 (2019) 1999–; doi:10.1039/C8GC03744B

data_7232467
_publ_section_title
;
 Cooperative iridium complex-catalyzed synthesis of quinoxalines,
 benzimidazoles and quinazolines in water
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              1999
_journal_paper_doi               10.1039/C8GC03744B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C18 H24 Cl Ir N3 O, C H2 Cl2, Cl'
_chemical_formula_sum            'C19 H26 Cl4 Ir N3 O'
_chemical_formula_weight         646.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-11-09 deposited with the CCDC.    2019-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.994(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.768(3)
_cell_length_b                   14.165(3)
_cell_length_c                   13.588(3)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.36
_cell_volume                     2278.7(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         2.767
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.344
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5146
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0849 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.6901.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.665
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+3.5670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0591
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5206
_reflns_number_total             5634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc03744b2.cif
_cod_data_source_block           14mayb_0m
_cod_depositor_comments          'Adding full bibliography for 7232467.cif.'
_cod_original_cell_volume        2278.6(10)
_cod_database_code               7232467
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C7(H7), C11(H11), C2AA(H2AA)
2.c Idealised Me refined as rotating group:
 C6AA(H6AA,H6AB,H6AC), C5AA(H5AA,H5AB,H5AC), C4AA(H4AA,H4AB,H4AC), C12(H12A,
 H12B,H12C), C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              42657
_olex2_submission_special_instructions 'No special instructions were received'