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_1555880
_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         'C31 H21 N O2'
_chemical_formula_sum            'C31 H21 N O2'
_chemical_formula_weight         439.49
_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
_audit_creation_date             2015-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                74.29(3)
_cell_angle_beta                 78.02(4)
_cell_angle_gamma                74.27(4)
_cell_formula_units_Z            2
_cell_length_a                   9.247(6)
_cell_length_b                   10.736(4)
_cell_length_c                   12.601(5)
_cell_measurement_reflns_used    336
_cell_measurement_temperature    294.6(6)
_cell_measurement_theta_max      17.6710
_cell_measurement_theta_min      3.5730
_cell_volume                     1146.9(10)
_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      294.6(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -52.00   32.00   2.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -19.0000 -180.0000 42

  2 omega   -8.00   24.00   2.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000 -150.0000 16

  3 omega  -19.00   61.00   2.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -99.0000 -180.0000 40

  4 omega  -11.00   23.00   2.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000  -30.0000 17

  5 omega  -46.00   42.00   2.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -60.0000 44

  6 omega  -22.00   36.00   2.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000   60.0000 29
;
_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      0.0786793000
_diffrn_orient_matrix_UB_12      -0.0211820000
_diffrn_orient_matrix_UB_13      0.0040771000
_diffrn_orient_matrix_UB_21      -0.0140954000
_diffrn_orient_matrix_UB_22      0.0189795000
_diffrn_orient_matrix_UB_23      0.0515791000
_diffrn_orient_matrix_UB_31      -0.0098887000
_diffrn_orient_matrix_UB_32      -0.0645040000
_diffrn_orient_matrix_UB_33      0.0285565000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1533
_diffrn_reflns_av_unetI/netI     0.3813
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6897
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.515
_diffrn_reflns_theta_min         3.404
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82589
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.3872
_refine_ls_R_factor_gt           0.0953
_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^)+(0.0658P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.3364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                679
_reflns_number_total             4226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02813_si_002.cif
_cod_data_source_block           qiuyf_0614
_cod_original_cell_volume        1146.8(10)
_cod_database_code               1555880
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C18(H18), C21(H21), C22(H22), C23(H23), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-17
_olex2_submission_special_instructions 'No special instructions were received'