Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions.
Brittain, William David George; Cobb, Steven L.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03322

data_4038406
_publ_section_title
;
 Protecting Group Controlled Remote Regioselective Electrophilic Aromatic
 Halogenation Reactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03322
_journal_year                    2020
_chemical_formula_moiety         'C20 H13 F4 I2 N O2'
_chemical_formula_sum            'C20 H13 F4 I2 N O2'
_chemical_formula_weight         629.11
_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             2019-06-04
_audit_creation_method
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Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.170(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3523(3)
_cell_length_b                   12.7890(3)
_cell_length_c                   12.8327(3)
_cell_measurement_reflns_used    6082
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.5080
_cell_measurement_theta_min      2.2550
_cell_volume                     2021.86(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   37.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000    0.0000 61

  2 omega   30.00   86.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -60.0000 56

  3 omega   64.00   97.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -150.0000 33

  4 omega   12.00   90.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   90.0000 78

  5 omega   -1.00   97.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  120.0000 98

  6 omega   28.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -30.0000 43

  7 omega  -16.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -150.0000 87
;
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0090851000
_diffrn_orient_matrix_UB_12      0.0473006000
_diffrn_orient_matrix_UB_13      -0.0281390000
_diffrn_orient_matrix_UB_21      -0.0078383000
_diffrn_orient_matrix_UB_22      0.0266819000
_diffrn_orient_matrix_UB_23      0.0473534000
_diffrn_orient_matrix_UB_31      0.0562814000
_diffrn_orient_matrix_UB_32      0.0113597000
_diffrn_orient_matrix_UB_33      0.0061343000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.497
_diffrn_reflns_theta_min         2.295
_diffrn_source                   'sealed tubeEnhance (Mo) X-ray Source'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.163
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_description       prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0290P)^2^+0.4130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4454
_reflns_number_total             5635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03322_si_003.cif
_cod_data_source_block           8_19srv190
_cod_original_cell_volume        2021.86(9)
_cod_database_code               4038406
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C20 H13 N1 O2 F4 I2'
_shelx_estimated_absorpt_t_max   0.648
_shelx_estimated_absorpt_t_min   0.379
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'