Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles.
Cao, Bo; Simaan, Marwan; Marek, Ilan; Wei, Yin; Shi, Min; Chemical communications (Cambridge, England) 53 (2016) 216–219; doi:10.1039/c6cc08731k

data_7119602
_publ_section_title
;
 Palladium-catalyzed oxidative cyclization of aniline-tethered
 alkylidenecyclopropanes with O2: a facile protocol to selectively
 synthesize 2- and 3-vinylindoles.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              216
_journal_page_last               219
_journal_paper_doi               10.1039/c6cc08731k
_journal_volume                  53
_journal_year                    2016
_chemical_formula_moiety         'C23 H18 Br N O2 S'
_chemical_formula_sum            'C23 H18 Br N O2 S'
_chemical_formula_weight         452.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-07 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                99.900(2)
_cell_angle_beta                 92.142(2)
_cell_angle_gamma                100.863(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1381(12)
_cell_length_b                   10.1764(13)
_cell_length_c                   10.7753(14)
_cell_measurement_reflns_used    3987
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.28
_cell_volume                     966.9(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9817
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.631
_diffrn_reflns_theta_min         1.924
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.253
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0999 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.6021.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.559
_refine_diff_density_min         -1.357
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.2833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4715
_reflns_number_total             5886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08731k2.cif
_cod_data_source_block           mo_dm16418_0m
_cod_database_code               7119602
_shelx_estimated_absorpt_t_max   0.603
_shelx_estimated_absorpt_t_min   0.506
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.b X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              83805
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'