Synthesis of δ-carbolines via a Pd-catalyzed sequential reaction from 2-iodoanilines and N-tosyl-enynamines.
Cao, Jian; Xu, Yongping; Kong, Yulong; Cui, Yuming; Hu, Ziqiang; Wang, Guanhai; Deng, Yuan; Lai, Guoqiao; Organic letters 14 (2012) 38–41; doi:10.1021/ol2027762

data_1503475
_publ_section_title
;
 Synthesis of \d-carbolines via a Pd-catalyzed sequential reaction from
 2-iodoanilines and N-tosyl-enynamines.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              38
_journal_page_last               41
_journal_paper_doi               10.1021/ol2027762
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C23 H16 N2'
_chemical_formula_weight         320.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.2350(10)
_cell_angle_beta                 73.9740(10)
_cell_angle_gamma                80.1920(10)
_cell_formula_units_Z            4
_cell_length_a                   11.3832(6)
_cell_length_b                   11.7346(6)
_cell_length_c                   13.7133(7)
_cell_measurement_reflns_used    6132
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.19
_cell_volume                     1732.10(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18400
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0440
_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^)+(0.1136P)^2^+0.1796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                4583
_reflns_number_total             6197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2027762_si_001.cif
_cod_data_source_block           mo_20110623c_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Multi-scan'
changed to 'multi-scan' 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_cell_volume        1732.10(15)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               1503475