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_7158742
_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         'C25 H5 B F15 N O S'
_chemical_formula_sum            'C25 H5 B F15 N O S'
_chemical_formula_weight         663.17
_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
_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                 90.911(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9957(5)
_cell_length_b                   20.7143(7)
_cell_length_c                   16.4103(5)
_cell_measurement_reflns_used    9120
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.44
_cell_volume                     4756.9(3)
_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      150.0
_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  0.0848
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            92990
_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         68.374
_diffrn_reflns_theta_min         3.436
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5913
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0818 after correction.
The Ratio of minimum to maximum transmission is 0.7852.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_description       needle
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         8693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0388P)^2^+1.3067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7336
_reflns_number_total             8693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11_CCDC6
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H10 B2 F30 N2 O2 S2'
_cod_original_formula_weight         1326.34
_cod_original_formula_moiety         '2(C25 H5 B F15 N O S)'
_cod_original_formula_units_Z            4
_cod_database_code               7158742
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.685
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N00Z(H00Z), N1(H1), C01W(H01W), C024(H024), C22(H22), C24(H24), C21(H21),
 C23(H23), C02D(H02D), C02E(H02E)
;
_shelx_res_checksum              98868
_olex2_submission_special_instructions 'No special instructions were received'