One-Pot Synthesis of Enantiopure Spiro[3,4-dihydrobenzo[<i>b</i>][1,4]oxazine-2,3'-oxindole] via Regio- and Stereoselective Tandem Ring Opening/Cyclization of Spiroaziridine Oxindoles with Bromophenols.
Hajra, Saumen; Hazra, Atanu; Abu Saleh, S. K.; The Journal of organic chemistry 84 (2019) 10412–10421; doi:10.1021/acs.joc.9b01611

data_4034055
_publ_section_title
;
 One-Pot Synthesis of Enantiopure
 Spiro[3,4-dihydrobenzo[<i>b</i>][1,4]oxazine-2,3'-oxindole] via Regio-
 and Stereoselective Tandem Ring Opening/Cyclization of Spiroaziridine
 Oxindoles with Bromophenols.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10412
_journal_page_last               10421
_journal_paper_doi               10.1021/acs.joc.9b01611
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H23 Cl N2 O4 S'
_chemical_formula_sum            'C21 H23 Cl N2 O4 S'
_chemical_formula_weight         434.92
_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             2019-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.731(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0240(9)
_cell_length_b                   13.3762(13)
_cell_length_c                   18.311(2)
_cell_measurement_reflns_used    46529
_cell_measurement_temperature    273.0(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      2.323
_cell_volume                     2147.1(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.0(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            46529
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.323
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1707 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.8624. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0482P)^2^+1.0630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3518
_reflns_number_total             3705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01611_si_002.cif
_cod_data_source_block           mono_p_a
_cod_original_cell_volume        2147.2(4)
_cod_database_code               4034055
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.920
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15), C14(H14), C6(H6), C12(H12)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'