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_7125456
_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         'C24 H18 Cl N O2'
_chemical_formula_sum            'C24 H18 Cl N O2'
_chemical_formula_weight         387.84
_chemical_name_common
2-(3-benzoyl-6-chloro-2-phenyl-1,4-dihydro-4-quinolinyl)acetaldehyde
_chemical_name_systematic
2-(3-benzoyl-6-chloro-2-phenyl-1,4-dihydro-4-quinolinyl)acetaldehyde
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-05-31 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.1510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9587(3)
_cell_length_b                   7.7456(2)
_cell_length_c                   22.4121(7)
_cell_measurement_reflns_used    267
_cell_measurement_temperature    296.15(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.3
_cell_volume                     1872.60(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1004
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            66778
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.85
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.224
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lustrous,light,needle
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0089(14)
_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   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0783
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.6845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                2619
_reflns_number_total             3714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc03269f2.cif
_cod_data_source_block           a
_cod_database_code               7125456
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'