Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids.
Hartung, Christian G.; Fecher, Anja; Chapell, Brian; Snieckus, Victor; Organic letters 5 (2003) 1899–1902; doi:10.1021/ol0344772

data_1507311
_publ_contact_author             'Victor Snieckus'
_publ_section_title
;
 Directed ortho metalation approach to C-7-substituted indoles.
 Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone
 alkaloids.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              1899
_journal_page_last               1902
_journal_paper_doi               10.1021/ol0344772
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C21 H32 N O P'
_chemical_formula_weight         345.45
_chemical_melting_point          371
_chemical_name_systematic
1-(Di-tert-butylphosphinoyl)-7-(3-methylbut-2-enyl)-indole
_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                 107.92(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.408(1)
_cell_length_b                   14.560(1)
_cell_length_c                   11.487(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      14.13
_cell_measurement_theta_min      9.83
_cell_volume                     1974.6(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       XSCANS
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       Omega
_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  0.0101
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4050
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        +/-1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Face-indexed analytical'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle Prism'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.92
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0118(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.629
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.629
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                3294
_reflns_number_total             3868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0344772si20030319_094727.cif
_cod_data_source_block           bc835
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Integration'
changed to 'integration' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507311