Photocatalyst-free regioselective sulfonamidation of <i>N</i>-(2-hydroxyaryl)amides in visible-light.
Rajat, ?; Rajput, Shruti; Grover, Nitika; Jain, Nidhi; Organic & biomolecular chemistry 22 (2024) 8649–8655; doi:10.1039/d4ob01393j

data_7160158
_publ_section_title
;
 Photocatalyst-free regioselective sulfonamidation of
 <i>N</i>-(2-hydroxyaryl)amides in visible-light.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8649
_journal_page_last               8655
_journal_paper_doi               10.1039/d4ob01393j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H16 N2 O4 S'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-06-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-07-12 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                84.04(3)
_cell_angle_beta                 75.55(3)
_cell_angle_gamma                76.36(3)
_cell_formula_units_Z            2
_cell_length_a                   7.453(4)
_cell_length_b                   10.846(5)
_cell_length_c                   11.701(6)
_cell_measurement_reflns_used    4809
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.58
_cell_volume                     889.1(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0680
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21802
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.799
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1255 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.7468.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.277
_refine_ls_extinction_coef       0.49(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.316
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.316
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0972
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2816
_refine_ls_wR_factor_ref         0.3037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2500
_reflns_number_total             3112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01393j2.cif
_cod_data_source_block           rajat_nts_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160158.cif.'
_cod_original_cell_volume        889.1(7)
_cod_database_code               7160158
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.997
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(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:
 N1(H1), C2(H2), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 58 electrons were 
found in a volume of 182\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[CHCl3] per Asymmetric Unit 
which account for 58 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              66941
_shelx_fab_checksum              35764
_olex2_submission_special_instructions 'No special instructions were received'