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_7158740
_publ_section_title
;
 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         'C18 H15 N O6 S'
_chemical_formula_sum            'C18 H15 N O6 S'
_chemical_formula_weight         373.37
_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   geom
_atom_sites_solution_primary     dual
_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                90.6280(10)
_cell_angle_beta                 94.4890(10)
_cell_angle_gamma                101.8900(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3619(3)
_cell_length_b                   8.0345(3)
_cell_length_c                   13.9973(5)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.09
_cell_measurement_theta_min      3.17
_cell_volume                     807.37(5)
_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 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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0217
_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       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24386
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.125
_diffrn_reflns_theta_max         65.125
_diffrn_reflns_theta_min         3.168
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6477
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1238 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8606.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0354P)^2^+0.5059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2655
_reflns_number_total             2752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11_CCDC4
_cod_database_code               7158740
_shelx_shelxl_version_number     2018/3
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C2(H2), C7(H7), C13(H13), C17(H17), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              50305
_olex2_submission_special_instructions 'No special instructions were received'