Regioselective Brønsted acid catalyzed ring opening of aziridines by phenols and thiophenols; a gateway to access functionalized indolines, indoles, benzothiazines, dihydrobenzo-thiazines, benzo-oxazines and benzochromenes.
Roy, Arnab; Duari, Surajit; Maity, Srabani; Biswas, Subrata; Mishra, Abhishek Kumar; Biswas, Srijit; Organic & biomolecular chemistry 22 (2024) 5653–5664; doi:10.1039/d4ob00196f

data_7159972
_publ_section_title
;
 Regioselective Br&#xf8;nsted acid catalyzed ring opening of aziridines by
 phenols and thiophenols; a gateway to access functionalized indolines,
 indoles, benzothiazines, dihydrobenzo-thiazines, benzo-oxazines and
 benzochromenes.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5653
_journal_page_last               5664
_journal_paper_doi               10.1039/d4ob00196f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C25 H24 Cl N O7 S'
_chemical_formula_sum            'C25 H24 Cl N O7 S'
_chemical_formula_weight         517.96
_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             2023-09-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-11-10 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                97.653(6)
_cell_angle_beta                 104.022(7)
_cell_angle_gamma                92.139(7)
_cell_formula_units_Z            4
_cell_length_a                   12.317(3)
_cell_length_b                   12.681(3)
_cell_length_c                   18.882(4)
_cell_measurement_reflns_used    6301
_cell_measurement_temperature    175.06
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.39
_cell_volume                     2828.4(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      175.06
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_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  0.1068
_diffrn_reflns_av_unetI/netI     0.1360
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34652
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.248
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5380
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1446 before and 0.0989 after correction.
The Ratio of minimum to maximum transmission is 0.7217.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull yellowish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0046(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     638
_refine_ls_number_reflns         12860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0863P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.2138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6198
_reflns_number_total             12860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00196f2.cif
_cod_data_source_block           mo_sbcu120923par_0m
_cod_depositor_comments          'Adding full bibliography for 7159972.cif.'
_cod_original_cell_volume        2828.2(10)
_cod_database_code               7159972
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.961
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C20(H20), C21(H21), C23(H23), C24(H24), N2(H2), C28(H28), C29(H29),
 C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C45(H45),
  C46(H46), C48(H48), C49(H49)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C41(H41A,H41B,
 H41C), C43(H43A,H43B,H43C), C50(H50A,H50B,H50C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              46152
_shelx_fab_checksum              6657
_olex2_submission_special_instructions 'No special instructions were received'