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_7056485
_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         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_chemical_melting_point          412.5(15)
_chemical_name_systematic
'Ethyl 4-(3-hydroxy-3-methylbut-1-yn-1-yl)-6-methoxyquinoline-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   mixed
_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                94.646(2)
_cell_angle_beta                 108.461(2)
_cell_angle_gamma                96.454(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2169(5)
_cell_length_b                   9.1554(5)
_cell_length_c                   11.7431(7)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.26
_cell_volume                     826.25(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    SIR2014
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0222
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23410
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         1.842
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       irregular
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0608P)^2^+0.2022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2982
_reflns_number_total             3378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj01803g2.cif
_cod_data_source_block           JZS8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '411-414' was changed to '412.5(15)'
- 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               7056485
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
_shelx_res_checksum              75001