Modular, One-Pot, Sequential Aziridine Ring Opening-S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams.
Loh, Joanna K.; Asad, Naeem; Samarakoon, Thiwanka B.; Hanson, Paul R.; The Journal of organic chemistry 80 (2015) 9926–9941; doi:10.1021/acs.joc.5b01429

data_4036296
_publ_section_title
;
 Modular, One-Pot, Sequential Aziridine Ring Opening-S(N)Ar Strategy to
 7-, 10-, and 11-Membered Benzo-Fused Sultams.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9926
_journal_page_last               9941
_journal_paper_doi               10.1021/acs.joc.5b01429
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ads
_chemical_formula_sum            'C15.5 H24 Br Cl N2 O3 S'
_chemical_formula_weight         433.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.9062(10)
_cell_length_b                   13.2212(11)
_cell_length_c                   22.5828(18)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.87
_cell_volume                     3853.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Platinum 135 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22577
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         68.321
_diffrn_reflns_theta_min         3.874
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    5.331
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 2762 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.032(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         6755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0333P)^2^+0.9202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                6575
_reflns_number_total             6755
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01429_si_002.cif
_cod_data_source_block           v80b_Cmpd_10m
_cod_original_formula_sum        'C15.50 H24 Br Cl N2 O3 S'
_cod_database_code               4036296
_shelx_estimated_absorpt_t_min   0.250
_shelx_estimated_absorpt_t_max   0.924
_shelxl_version_number           2013-4
_shelx_res_checksum              62053
_shelx_hkl_checksum              81368