Metal-free C8-H functionalization of quinoline <i>N</i>-oxides with ynamides.
Hu, Weican; Zhang, Feiyang; Chen, Chen; Qi, Tianhang; Shen, Yanlong; Qian, Guoying; Rong, Zhouting; Chemical communications (Cambridge, England) 57 (2021) 6995–6998; doi:10.1039/d1cc02138a

data_7128525
_publ_section_title
;
 Metal-free C8-H functionalization of quinoline <i>N</i>-oxides with
 ynamides.
;
_journal_issue                   57
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6995
_journal_page_last               6998
_journal_paper_doi               10.1039/d1cc02138a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C19 H18 N2 O3 S'
_chemical_formula_sum            'C19 H18 N2 O3 S'
_chemical_formula_weight         354.432
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27686y
_audit_creation_date             2020-06-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-02-07 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.951(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.124(3)
_cell_length_b                   7.6958(15)
_cell_length_c                   16.5624(16)
_cell_measurement_reflns_used    1843
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.5020
_cell_measurement_theta_min      2.5010
_cell_volume                     3452.7(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9613
_diffrn_measured_fraction_theta_max 0.9613
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -45.00  32.00   1.00   10.00    --   15.65 -57.00   0.00   77
  2  \w    -16.00  10.00   1.00   10.00    --  -16.43 -99.00 -60.00   26
  3  \w    -84.00   6.00   1.00   10.00    --  -16.43 -77.00-120.00   90
  4  \w     18.00  46.00   1.00   10.00    --  -16.43  57.00 -90.00   28
  5  \w     43.00  83.00   1.00   10.00    --   15.65 178.00-180.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0234852000
_diffrn_orient_matrix_UB_12      -0.0070242000
_diffrn_orient_matrix_UB_13      0.0206841000
_diffrn_orient_matrix_UB_21      0.0042320000
_diffrn_orient_matrix_UB_22      0.0898215000
_diffrn_orient_matrix_UB_23      -0.0066104000
_diffrn_orient_matrix_UB_31      -0.0107849000
_diffrn_orient_matrix_UB_32      0.0196533000
_diffrn_orient_matrix_UB_33      0.0369769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_Laue_measured_fraction_full 0.9613
_diffrn_reflns_Laue_measured_fraction_max 0.9613
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9517
_diffrn_reflns_point_group_measured_fraction_full 0.9613
_diffrn_reflns_point_group_measured_fraction_max 0.9613
_diffrn_reflns_theta_full        24.9977
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             1489.673
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.5479
_refine_diff_density_min         -0.5320
_refine_diff_density_rms         0.1382
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             8.2702
_refine_ls_goodness_of_fit_ref   1.0482
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0482
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.1076
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1784P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2587
_refine_ls_wR_factor_ref         0.2998
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              0
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                1825
_reflns_number_total             2910
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1cc02138a2.cif
_cod_data_source_block           exp_7989
_cod_depositor_comments          'Adding full bibliography for 7128525.cif.'
_cod_original_cell_volume        3452.7(9)
_cod_original_sg_symbol_Hall     '-C 2yc (x+z,y,-x)'
_cod_database_code               7128525
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C18(H18), C14(H14), C3(H3), C16(H16), C12(H12),
 C17(H17), C13(H13)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C7(H7a,H7b,H7c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.053
_oxdiff_exptl_absorpt_empirical_full_min 0.533