Transition metal-free one-pot double C-H functionalization of quinolines with disubstituted electron-deficient acetylenes.
Trofimov, B. A.; Belyaeva, K. V.; Nikitina, L. P.; Mal'kina, A. G.; Afonin, A. V.; Ushakov, I. A.; Vashchenko, A. V.; Chemical communications (Cambridge, England) 54 (2018) 5863–5866; doi:10.1039/c8cc03269f

data_7125458
_publ_section_title
;
 Transition metal-free one-pot double C-H functionalization of quinolines
 with disubstituted electron-deficient acetylenes.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5863
_journal_page_last               5866
_journal_paper_doi               10.1039/c8cc03269f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C20 H13 N O2'
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31
_chemical_name_systematic        2-furyl(2-phenyl-3-quinolinyl)methanone
_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     direct
_audit_creation_date             2016-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-31 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.183(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1150(9)
_cell_length_b                   16.3598(14)
_cell_length_c                   7.7826(6)
_cell_measurement_reflns_used    391
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.45
_cell_volume                     1465.5(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 0.77
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  None
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            46541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.163
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1643 before and 0.0827 after correction.
The Ratio of minimum to maximum transmission is 0.8479.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       irregular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0112(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.9182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2950
_reflns_number_total             3373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03269f2.cif
_cod_data_source_block           a_CCDC1
_cod_database_code               7125458
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              41976
_shelx_hkl_checksum              13914
_olex2_submission_special_instructions 'No special instructions were received'