<i>ortho</i>-Functionalization of azobenzenes <i>via</i> hypervalent iodine reagents.
Di Tommaso, Ester Maria; Walther, Melanie; Staubitz, Anne; Olofsson, Berit; Chemical communications (Cambridge, England) 59 (2023) 5047–5050; doi:10.1039/d3cc01060k

data_7131498
_publ_section_title
;
 <i>ortho</i>-Functionalization of azobenzenes <i>via</i> hypervalent
 iodine reagents.
;
_journal_issue                   34
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5047
_journal_page_last               5050
_journal_paper_doi               10.1039/d3cc01060k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C19 H16 I N2 O, C7 H7 O3 S'
_chemical_formula_sum            'C26 H23 I N2 O4 S'
_chemical_formula_weight         586.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2022-10-27 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.131(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8892(4)
_cell_length_b                   16.7789(11)
_cell_length_c                   14.1591(7)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.37
_cell_volume                     2325.8(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0475
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            73815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_min         2.363
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.504
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1445 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.018
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0128P)^2^+7.1522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4967
_reflns_number_total             5789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01060k3.cif
_cod_data_source_block           walterm2100217_0ma
_cod_depositor_comments          'Adding full bibliography for 7131498.cif.'
_cod_database_code               7131498
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.585
_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
2.a Me refined with everything fixed:
 C19(H19A,H19B,H19C)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C14(H14), C5(H5), C25(H25), C22(H22), C11(H11), C6(H6),
 C21(H21), C15(H15), C10(H10), C18(H18), C24(H24), C17(H17), C4(H4), C9(H9),
 C8(H8)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              38936
_shelx_hkl_checksum              88405
_olex2_submission_special_instructions 'No special instructions were received'