4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry
Rodríguez, Diego; Guerrero, Sergio Andrés; Palma, Alirio; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 76 (2020) –; doi:10.1107/S2053229620010803

data_2022229
_publ_section_title
;
 4-Styrylquinolines from cyclocondensation reactions between
 (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and
 regiochemistry
;
_journal_coeditor_code           SK3755
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620010803
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C21 H18 Br N O2'
_chemical_formula_moiety         'C21 H18 Br N O2'
_chemical_formula_sum            'C21 H18 Br N O2'
_chemical_formula_weight         396.26
_chemical_name_common
;
Ethyl (<i>E</i>)-4-(4-bromostyryl)-2-methylquinoline-3-carboxylate
;
_chemical_name_systematic
;
Ethyl (<i>E</i>)-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline-3-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90.939(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5709(6)
_cell_length_b                   10.6119(7)
_cell_length_c                   18.2074(10)
_cell_measurement_reflns_used    4558
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.304
_cell_measurement_theta_min      2.221
_cell_volume                     1849.0(2)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            54534
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.221
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.236
_exptl_absorpt_correction_T_max  0.715
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0237P)^2^+1.0895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0558
_reflns_number_gt                4098
_reflns_number_total             4588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3755sup1.cif
_cod_data_source_block           V
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022229
_cod_database_fobs_code          2022229
_shelx_estimated_absorpt_t_min   0.605
_shelx_estimated_absorpt_t_max   0.730
_shelx_hkl_checksum              69763
_shelx_res_checksum              38350
_shelxl_version_number           2.014