Samarium(III)-Catalyzed C(sp(3))-H Bond Activation: Synthesis of Indolizines via C-C and C-N Coupling between 2-Alkylazaarenes and Propargylic Alcohols.
Wang, Xu; Li, Shen-Yan; Pan, Ying-Ming; Wang, Heng-Shan; Liang, Hong; Chen, Zhen-Feng; Qin, Xiao-Huan; Organic letters 16 (2014) 580–583; doi:10.1021/ol4034513

data_1513412
_publ_section_title
;
 Samarium(III)-Catalyzed C(sp(3))-H Bond Activation: Synthesis of
 Indolizines via C-C and C-N Coupling between 2-Alkylazaarenes and
 Propargylic Alcohols.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              580
_journal_page_last               583
_journal_paper_doi               10.1021/ol4034513
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C22 H15 Cl N2'
_chemical_formula_weight         342.79
_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                110.20(3)
_cell_angle_beta                 92.26(3)
_cell_angle_gamma                106.10(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6705(17)
_cell_length_b                   10.194(2)
_cell_length_c                   10.926(2)
_cell_measurement_temperature    293(2)
_cell_volume                     860.9(4)
_computing_cell_refinement       SMART
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9906
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+0.0938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3049
_reflns_number_total             3513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4034513_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/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_cell_volume        860.9(3)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               1513412