Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst
Dinh, Andrew N.; Maddox, Sean M.; Vaidya, Sagar D.; Saputra, Mirza A.; Nalbandian, Christopher J.; Gustafson, Jeffrey L.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01917

data_4038888
_publ_section_title
;
 Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines
 through a Lewis Basic Selenoether Catalyst
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01917
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 F6 N3, Cl'
_chemical_formula_sum            'C15 H16 Cl F6 N3'
_chemical_formula_weight         387.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.950(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5346(5)
_cell_length_b                   15.4968(7)
_cell_length_c                   10.7550(6)
_cell_measurement_reflns_used    1637
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.472
_cell_measurement_theta_min      4.495
_cell_volume                     1639.71(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.1130
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12255
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.556
_diffrn_reflns_theta_min         4.402
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.709
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.1915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0873 before and 0.0696 after correction. The Ratio of minimum to maximum transmission is 0.5984. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       Needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0638P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3825
_reflns_number_total             5851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01917_si_002.cif
_cod_data_source_block           Gustafson05
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038888
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1'-H1' = N3'-H3' = N2'-H2' = N2-H2 = N1-H1 = N3-H3
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C1'(H1'A), C2'(H2'A)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C3'(H3'A,H3'B), C4'(H4'A,
 H4'B), C5'(H5'A,H5'B), C6'(H6'A,H6'B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C13(H13), C9'(H9'), C11'(H11'), C13'(H13')
;
_shelx_res_checksum              2317
_shelx_hkl_checksum              67283
_olex2_submission_special_instructions 'No special instructions were received'