Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one.
Wang, Mengzhou; Zhang, Yanyan; Wang, Tao; Wang, Chao; Xue, Dong; Xiao, Jianliang; Organic letters 18 (2016) 1976–1979; doi:10.1021/acs.orglett.6b00547

data_1555520
_publ_section_title
;
 Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and
 Heterocycles by 1-Chloro-1,2-benziodoxol-3-one.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1976
_journal_page_last               1979
_journal_paper_doi               10.1021/acs.orglett.6b00547
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C9 H7 Cl N2'
_chemical_formula_sum            'C9 H7 Cl N2'
_chemical_formula_weight         178.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8146(3)
_cell_length_b                   3.92480(10)
_cell_length_c                   20.5530(6)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    153
_cell_measurement_theta_max      30.480
_cell_measurement_theta_min      3.260
_cell_volume                     771.35(4)
_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      153.01
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23789
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.130
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1499 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.9338.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0496P)^2^+0.6663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2123
_reflns_number_total             2352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00547_si_003.cif
_cod_data_source_block           z
_cod_database_code               1555520
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'