Efficient Carbazole Synthesis via Pd/Cu-Cocatalyzed Cross-Coupling/Isomerization of 2-Allyl-3-iodoindoles and Terminal Alkynes.
Zhu, Can; Ma, Shengming; Organic letters 16 (2014) 1542–1545; doi:10.1021/ol500119r

data_1513933
_publ_section_title
;
 Efficient Carbazole Synthesis via Pd/Cu-Cocatalyzed
 Cross-Coupling/Isomerization of 2-Allyl-3-iodoindoles and Terminal
 Alkynes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1542
_journal_page_last               1545
_journal_paper_doi               10.1021/ol500119r
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C20 H17 N O2 S'
_chemical_formula_weight         335.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.040(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.928(2)
_cell_length_b                   11.9718(19)
_cell_length_c                   11.6528(18)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.341
_cell_measurement_theta_min      4.843
_cell_volume                     1647.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8407
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74912
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.231
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.3743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2629
_reflns_number_total             3231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500119r_si_002.cif
_cod_data_source_block           cd211409
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1513933