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_2022227
_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 H16 F3 N O'
_chemical_formula_moiety         'C21 H16 F3 N O'
_chemical_formula_sum            'C21 H16 F3 N O'
_chemical_formula_weight         355.35
_chemical_name_common
;
(<i>E</i>)-3-Acetyl-2-methyl-4-[4-(trifluoromethyl)styryl]quinoline
;
_chemical_name_systematic
;
(<i>E</i>)-3-Acetyl-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0822(4)
_cell_length_b                   6.6567(4)
_cell_length_c                   32.1024(17)
_cell_measurement_reflns_used    3961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.511
_cell_measurement_theta_min      2.520
_cell_volume                     1727.05(16)
_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 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            19648
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.520
_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    0.106
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0390P)^2^+0.8719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3363
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3755sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022227
_cod_database_fobs_code          2022227
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.994
_shelx_hkl_checksum              11092
_shelx_res_checksum              14244
_shelxl_version_number           2.014