NBS-induced intramolecular annulation reactions for the divergent synthesis of fused- and spirocyclic indolines.
Luo, Xian; Xu, Meng-Meng; Xu, Xiao-Ping; Ji, Shun-Jun; Chemical communications (Cambridge, England) 59 (2023) 6576–6579; doi:10.1039/d3cc01920a

data_7131607
_publ_section_title
;
 NBS-induced intramolecular annulation reactions for the divergent
 synthesis of fused- and spirocyclic indolines.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6576
_journal_page_last               6579
_journal_paper_doi               10.1039/d3cc01920a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C16 H14 Br2 F6 N2 O3'
_chemical_formula_sum            'C16 H14 Br2 F6 N2 O3'
_chemical_formula_weight         556.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.610(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5935(8)
_cell_length_b                   10.4364(9)
_cell_length_c                   10.8779(9)
_cell_measurement_reflns_used    8031
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.71
_cell_volume                     972.43(15)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14095
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.709
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.245
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1638 before and 0.1033 after correction.
The Ratio of minimum to maximum transmission is 0.4492.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.129(8)
_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     264
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0507P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3460
_reflns_number_total             4345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01920a2.cif
_cod_data_source_block           b210926a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7131607--7131608.cif.'
_cod_database_code               7131607
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.728
_shelx_estimated_absorpt_t_min   0.417
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C14(H14)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              76056
_shelx_hkl_checksum              41559
_olex2_submission_special_instructions 'No special instructions were received'