Catalyst-dependent chemoselective insertion of diazoalkanes into N-HΧ-HΟ-HΧ-O bonds of 2-hydroxybenzothiazoles
Jin, Lvnan; Zhou, Xuan; Zhao, Yunbo; Guo, Jing; Stephan, Douglas W.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01048H

data_7158739
_publ_section_title
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 Catalyst-dependent chemoselective insertion of diazoalkanes into
 N-H\C-H\O-H\C-O bonds of 2-hydroxybenzothiazoles
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01048H
_journal_year                    2022
_chemical_formula_moiety         'C16 H11 Br Cl N O3 S'
_chemical_formula_sum            'C16 H11 Br Cl N O3 S'
_chemical_formula_weight         412.68
_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
_audit_creation_date             2022-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1958(3)
_cell_length_b                   15.7734(5)
_cell_length_c                   9.1550(3)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.57
_cell_measurement_theta_min      3.97
_cell_volume                     1607.47(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29115
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.561
_diffrn_reflns_theta_min         3.971
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.355
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8317.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0234
_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^)+(0.0317P)^2^+0.6734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2894
_reflns_number_total             3180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11_CCDC3
_cod_database_code               7158739
_shelx_shelxl_version_number     2018/3
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C13(H13), C12(H12), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              54257
_olex2_submission_special_instructions 'No special instructions were received'