Iodine(III)-Enabled Distal C-H Functionalization of Biarylsulfonanilides.
Bal, Ankita; Maiti, Saikat; Mal, Prasenjit; The Journal of organic chemistry 83 (2018) 11278–11287; doi:10.1021/acs.joc.8b01857

data_4035633
_publ_section_title
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 Iodine(III)-Enabled Distal C-H Functionalization of Biarylsulfonanilides.
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_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11278
_journal_page_last               11287
_journal_paper_doi               10.1021/acs.joc.8b01857
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H25 N O3 S'
_chemical_formula_sum            'C24 H25 N O3 S'
_chemical_formula_weight         407.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_audit_creation_date             2018-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.1115(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.0269(4)
_cell_length_b                   11.51228(18)
_cell_length_c                   15.7204(3)
_cell_measurement_reflns_used    14086
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.8980
_cell_measurement_theta_min      2.4550
_cell_volume                     4234.97(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9800
_diffrn_measured_fraction_theta_max 0.9800
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16343
_diffrn_reflns_theta_full        79.4429
_diffrn_reflns_theta_max         79.44
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2783
_exptl_crystal_description       block
_exptl_crystal_F_000             1735.6808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.4529
_refine_diff_density_min         -0.5676
_refine_diff_density_rms         0.1175
_refine_ls_d_res_high            0.7842
_refine_ls_d_res_low             11.7002
_refine_ls_goodness_of_fit_ref   1.0278
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0278
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1134P)^2^+1.6913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1696
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              29
_reflns_limit_h_min              -30
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4102
_reflns_number_total             4504
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b01857_si_002.cif
_cod_data_source_block           pmal_348
_cod_original_cell_volume        4234.98(13)
_cod_database_code               4035633
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All F(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C00M(H00a,H00b), C00P(H00i,H00j)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C3(H3), C00H(H00H), C00K(H00K), C00L(H00L),
 C00N(H00N), C00Q(H00Q), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00O(H00c,H00f,H00g), C8(H8a,H8b,H8c), C00T(H00m,H00o,H00p)
2.d Idealised tetrahedral OH refined as rotating group:
 F005(H005)
;
_olex2_submission_special_instructions 'No special instructions were received'