Ytterbium(III)-Catalyzed Three-Component Reactions: Synthesis of 4-Organoselenium-quinolines and Application in Copper-free Sonogashira Cross-coupling Reactions
Stefani, Helio A.; Oliveira, Isadora M.; Vaconcelos, Stanley N. S.; Barbeiro, Cristiane S.; Carita Correra, Thiago; Shamim, Anwar; Pimenta, Daniel C.; Caracelli, Ignez; Zukerman-Schpector, Julio; Manarin, Flavia G.; New J. Chem. 41 (2017) 9884–9888; doi:10.1039/C7NJ01803G

data_7056484
_publ_section_title
;
 Ytterbium(III)-Catalyzed Three-Component Reactions: Synthesis of
 4-Organoselenium-quinolines and Application in Copper-free Sonogashira
 Cross-coupling Reactions
;
_journal_issue                   18
_journal_name_full               'New J. Chem.'
_journal_page_first              9884
_journal_page_last               9888
_journal_paper_doi               10.1039/C7NJ01803G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C19 H17 N O3 Se'
_chemical_formula_sum            'C19 H17 N O3 Se'
_chemical_formula_weight         386.29
_chemical_melting_point          394(3)
_chemical_name_systematic
'ethyl 6-methoxy-4-(phenylselanyl)quinoline-2-carboxylate '
_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
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-07-28 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                69.466(2)
_cell_angle_beta                 80.191(2)
_cell_angle_gamma                70.859(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1372(5)
_cell_length_b                   10.2407(4)
_cell_length_c                   10.3976(5)
_cell_measurement_reflns_used    6501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.36
_cell_volume                     859.05(7)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12521
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.556
_diffrn_reflns_theta_min         2.096
_exptl_absorpt_coefficient_mu    2.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       irregular
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.289
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.5584
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.4949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3017
_reflns_number_total             3555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj01803g2.cif
_cod_data_source_block           IC5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '391-396' was changed to '394(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7056484
_shelx_estimated_absorpt_t_min   0.485
_shelx_estimated_absorpt_t_max   0.569
_shelxl_version_number           2014/6
_shelx_res_checksum              69540