New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: synthesis via Buchwald–Hartwig amination, photophysics, and biomolecular binding properties
Bonacorso, Helio G.; Rodrigues, Melissa B.; Iglesias, Bernardo A.; da Silveira, Carolina H.; Feitosa, Sarah C.; Rosa, Wilian C.; Martins, Marcos A. P.; Frizzo, Clarissa P.; Zanatta, Nilo; New Journal of Chemistry 42 (2018) 10024–; doi:10.1039/C8NJ01120F

data_7057440
_publ_section_title
;
 New
 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines:
 synthesis via Buchwald--Hartwig amination, photophysics, and biomolecular
 binding properties
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10024
_journal_paper_doi               10.1039/C8NJ01120F
_journal_volume                  42
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H19 F3 N2'
_chemical_formula_sum            'C21 H19 F3 N2'
_chemical_formula_weight         356.38
_chemical_melting_point          ?
_chemical_name_common            6-(pyrrolidin-1-yl)toluyl-quinoline
_chemical_name_systematic
;
        '6-(pyrrolidin-1-yl)-2-(p-tolyl)-4-(trifluoromethyl)quinoline'
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-04-17T12:30:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-04-18 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.597(5)
_cell_length_b                   10.743(5)
_cell_length_c                   20.703(5)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.672
_cell_measurement_theta_min      2.7315
_cell_measurement_wavelength     0.71073
_cell_volume                     1689.7(14)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.019
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            57067
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.149
_diffrn_reflns_theta_min         2.733
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1344 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.5543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.085
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3385
_reflns_number_total             3738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01120f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7057440.cif.
;
_cod_database_code               7057440
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.994