Construction of 2,3-Quaternary Fused Indolines from Alkynyl tethered Oximes and Diaryliodonium Salts through A Cascade Strategy of N-Arylation/Cycloaddition/[3,3]-Rearrangement
Ma, Xiao-Pan; Li, Kun; Wu, Si-Yi; Liang, Cui; SU, Guifa; Mo, Dong-Liang; Green Chem.  (2017) –; doi:10.1039/C7GC02844J

data_7229453
_publ_section_title
;
 Construction of 2,3-Quaternary Fused Indolines from Alkynyl tethered
 Oximes and Diaryliodonium Salts through A Cascade Strategy of
 N-Arylation/Cycloaddition/[3,3]-Rearrangement
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC02844J
_journal_year                    2017
_chemical_formula_moiety         'C24 H17 Br2 N O2'
_chemical_formula_sum            'C24 H17 Br2 N O2'
_chemical_formula_weight         511.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-12 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.186(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8958(12)
_cell_length_b                   18.729(2)
_cell_length_c                   13.2336(18)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.216
_cell_measurement_theta_min      2.718
_cell_volume                     2094.7(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18359
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.95
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.890
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            light
_exptl_crystal_colour_modifier   light
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.284
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     281
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0844P)^2^+3.4632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1810
_reflns_number_gt                2740
_reflns_number_total             4305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7gc02844j2.cif
_cod_data_source_block           aaaa
_cod_database_code               7229453
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), N1(H1), C8(H8), C1(H1A), C14(H14), C18(H18), C11(H11), C3(H3),
 C13(H13), C22(H22), C23(H23), C24(H24), C20(H20), C21(H21), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'