Three-component ruthenium-catalyzed remote C-H functionalization of 8-aminoquinoline amides.
Shi, Wei-Yu; Ding, Ya-Nan; Liu, Ce; Zheng, Nian; Gou, Xue-Ya; Li, Ming; Zhang, Zhe; Liu, Hong-Chao; Niu, Zhi-Jie; Liang, Yong-Min; Chemical communications (Cambridge, England) 56 (2020) 12729–12732; doi:10.1039/d0cc05491g

data_7127268
_publ_section_title
;
 Three-component ruthenium-catalyzed remote C-H functionalization of
 8-aminoquinoline amides.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12729
_journal_page_last               12732
_journal_paper_doi               10.1039/d0cc05491g
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H28 F2 N2 O4'
_chemical_formula_sum            'C33 H28 F2 N2 O4'
_chemical_formula_weight         554.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2598wn
_audit_creation_date             2020-05-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-05-20 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.9151(4)
_cell_length_b                   13.9396(2)
_cell_length_c                   7.31714(13)
_cell_measurement_reflns_used    7507
_cell_measurement_temperature    293.01(11)
_cell_measurement_theta_max      69.5950
_cell_measurement_theta_min      4.5460
_cell_volume                     2745.29(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0367
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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    -15.00  42.00   1.00    1.00    --   54.00 -57.00  60.00   57
  2  \w     44.00  70.00   1.00    1.00    --  108.00-111.00  60.00   26
  3  \w     42.00 124.00   1.00    1.00    --  108.00 -63.00 -30.00   82
  4  \w     44.00 114.00   1.00    1.00    --  108.00-111.00-120.00   70
  5  \w     13.00  47.00   1.00    1.00    --   54.00 -57.00 -60.00   34
  6  \w    -12.00  22.00   1.00    1.00    --    0.00 -38.00-180.00   34
  7  \w    -64.00 -17.00   1.00    1.00    --    0.00 -38.00-180.00   47
  8  \w     86.00 169.00   1.00    1.00    --  108.00  63.00 -90.00   83
  9  \w    117.00 142.00   1.00    1.00    --  108.00  50.00 -60.00   25
 10  \w    105.00 150.00   1.00    1.00    --  108.00 111.00 -60.00   45
 11  \w     47.00 118.00   1.00    1.00    --   54.00  57.00 150.00   71
 12  \w    -48.00 -23.00   1.00    1.00    --    0.00 135.00 -61.00   25
 13  \w    -63.00 -37.00   1.00    1.00    --    0.00 135.00 118.00   26
 14  \w    -16.00   9.00   1.00    1.00    --   54.00 -77.00 -90.00   25
 15  \w     14.00  75.00   1.00    1.00    --   54.00 -99.00 -90.00   61
 16  \w     82.00 127.00   1.00    1.00    --  108.00 -63.00  60.00   45
 17  \w    111.00 164.00   1.00    1.00    --  108.00 111.00-120.00   53
 18  \w    104.00 140.00   1.00    1.00    --  108.00 111.00-180.00   36
 19  \w     92.00 118.00   1.00    1.00    --  108.00 -63.00-120.00   26
 20  \w     90.00 137.00   1.00    1.00    --  108.00 -25.00-150.00   47
 21  \w    -69.00  21.00   1.00    1.00    --    0.00 -57.00 -60.00   90
 22  \w    -21.00  69.00   1.00    1.00    --    0.00  57.00 120.00   90
 23  \w     33.00 123.00   1.00    1.00    --   54.00  57.00  30.00   90
 24  \w     24.00 124.00   1.00    1.00    --   54.00  77.00 -60.00  100
 25  \w     24.00  56.00   1.00    1.00    --   54.00  77.00  90.00   32
 26  \w     33.00 123.00   1.00    1.00    --   54.00  57.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0472842000
_diffrn_orient_matrix_UB_12      -0.0617246000
_diffrn_orient_matrix_UB_13      0.0156377000
_diffrn_orient_matrix_UB_21      -0.0033714000
_diffrn_orient_matrix_UB_22      0.0049901000
_diffrn_orient_matrix_UB_23      0.2098831000
_diffrn_orient_matrix_UB_31      -0.0320810000
_diffrn_orient_matrix_UB_32      -0.0915809000
_diffrn_orient_matrix_UB_33      0.0010707000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            14221
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.756
_diffrn_reflns_theta_min         3.571
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1320 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_coef       0.0028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0454P)^2^+0.0961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.677
_reflns_Friedel_fraction_max     0.658
_reflns_number_gt                4063
_reflns_number_total             4341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05491g2.cif
_cod_data_source_block           shiweiy_0518
_cod_depositor_comments          'Adding full bibliography for 7127268.cif.'
_cod_original_cell_volume        2745.29(8)
_cod_database_code               7127268
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.82
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C9(H9), C17(H17), C7(H7), C5(H5), C19(H19), C28(H28),
 C4(H4), C2(H2), C10(H10), C6(H6), C29(H29), C32(H32), C18(H18), C31(H31),
 C13(H13)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              92318
_olex2_date_sample_data_collection 2020-05-20
_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 4.163
_oxdiff_exptl_absorpt_empirical_full_min 0.457