Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates.
Saha, Moumita; Das, Asish R.; Organic & biomolecular chemistry 18 (2020) 941–955; doi:10.1039/c9ob02533b

data_7157305
_publ_section_title
;
 Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole,
 quinazoline and imidazopyridine as directing templates.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              941
_journal_page_last               955
_journal_paper_doi               10.1039/c9ob02533b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C14 H8 I2 N2'
_chemical_formula_sum            'C14 H8 I2 N2'
_chemical_formula_weight         458.02
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-29 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7487(17)
_cell_length_b                   8.3925(19)
_cell_length_c                   21.639(5)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      2.60
_cell_volume                     1407.2(6)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.033
_diffrn_reflns_theta_min         1.882
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.453
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1487 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.5805. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.162
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0188
_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^)+(0.0127P)^2^+0.7899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0426
_refine_ls_wR_factor_ref         0.0429
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2948
_reflns_number_total             3059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02533b2.cif
_cod_data_source_block           ard_ms_qz_i_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157305--7157306.cif.'
_cod_original_cell_volume        1407.2(5)
_cod_database_code               7157305
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.555
_shelx_estimated_absorpt_t_min   0.266
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I)
;
_shelx_res_checksum              30785
_olex2_submission_special_instructions 'No special instructions were received'