Metal-Free, Site-Selective Addition to Ynones: An Approach to Synthesize Substituted Quinoline Derivatives.
Chen, Zi-Sheng; Yang, Fang; Ling, Huibo; Li, Mengxue; Gao, Jin-Ming; Ji, Kegong; Organic letters 18 (2016) 5828–5831; doi:10.1021/acs.orglett.6b02813

data_1555879
_publ_section_title
;
 Metal-Free, Site-Selective Addition to Ynones: An Approach to Synthesize
 Substituted Quinoline Derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5828
_journal_page_last               5831
_journal_paper_doi               10.1021/acs.orglett.6b02813
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C25 H19 N O2'
_chemical_formula_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                96.666(13)
_cell_angle_beta                 95.878(14)
_cell_angle_gamma                102.772(13)
_cell_formula_units_Z            2
_cell_length_a                   6.3800(11)
_cell_length_b                   11.8204(17)
_cell_length_c                   13.095(2)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    300.79(10)
_cell_measurement_theta_max      69.3310
_cell_measurement_theta_min      6.8280
_cell_volume                     948.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.79(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega   16.00   68.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 26

  2 omega   39.00  123.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 42

  3 omega  103.00  171.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 34

  4 omega  100.00  148.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 24

  5 omega  107.00  133.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 13

  6 omega  142.00  168.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 13

  7 omega   91.00  173.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 41

  8 omega   89.00  163.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 37

  9 omega   60.00   96.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 18

 10 omega   54.00  114.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 30

 11 omega   46.00   94.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 24

 12 omega   39.00   93.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 27

 13 omega   39.00   67.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 14

 14 omega   58.00  108.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 25

 15 omega   71.00   97.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  120.0000 13

 16 omega   36.00   86.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   30.0000 25

 17 omega   36.00  138.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -60.0000 51

 18 omega   38.00   68.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 15

 19 omega   43.00   69.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 13

 20 omega   43.00   95.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 26

 21 omega    7.00   33.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 13

 22 omega  -13.00   55.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -30.0000 34

 23 omega  -19.00    7.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 13

 24 omega  -63.00  -37.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  136.0000 -116.0000 13

 25 omega   72.00  150.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 39

 26 omega  -13.00   69.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  120.0000 41

 27 omega  -15.00   81.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1494325000
_diffrn_orient_matrix_UB_12      0.0150784000
_diffrn_orient_matrix_UB_13      0.1032377000
_diffrn_orient_matrix_UB_21      -0.1918915000
_diffrn_orient_matrix_UB_22      0.0099910000
_diffrn_orient_matrix_UB_23      0.0601612000
_diffrn_orient_matrix_UB_31      -0.0569200000
_diffrn_orient_matrix_UB_32      -0.1338077000
_diffrn_orient_matrix_UB_33      -0.0011170000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5846
_diffrn_reflns_theta_full        69.88
_diffrn_reflns_theta_max         69.88
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0601P)^2^+0.2122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                2795
_reflns_number_total             3465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02813_si_003.cif
_cod_data_source_block           qiuyf_68c
_cod_database_code               1555879
_reflns_odcompleteness_completeness 98.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_date_sample_data_collection 2015-07-22
_olex2_submission_special_instructions 'No special instructions were received'