Rh(III)-Catalyzed C(8)-H Functionalization of Quinolines via Simultaneous C-C and C-O Bond Formation: Direct Synthesis of Quinoline Derivatives with Antiplasmodial Potential.
Sharma, Ritika; Kumar, Rakesh; Kumar, Rohit; Upadhyay, Pooja; Sahal, Dinkar; Sharma, Upendra; The Journal of organic chemistry 83 (2018) 12702–12710; doi:10.1021/acs.joc.8b02042

data_4035415
_publ_section_title
;
 Rh(III)-Catalyzed C(8)-H Functionalization of Quinolines via Simultaneous
 C-C and C-O Bond Formation: Direct Synthesis of Quinoline Derivatives
 with Antiplasmodial Potential.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12702
_journal_page_last               12710
_journal_paper_doi               10.1021/acs.joc.8b02042
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_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             2017-12-01
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                95.656(8)
_cell_angle_beta                 90.175(7)
_cell_angle_gamma                92.454(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8238(8)
_cell_length_b                   9.7981(10)
_cell_length_c                   10.3639(9)
_cell_measurement_reflns_used    1846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5690
_cell_measurement_theta_min      5.0160
_cell_volume                     890.82(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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    -42.00  62.00   1.00    1.00    --   25.57 -57.00 -60.00  104
  2  \w     39.00  88.00   1.00    1.00    --   66.78 -45.00  30.00   49
  3  \w     85.00 167.00   1.00    1.00    --  108.00 -21.00  30.00   82
  4  \w    144.00 178.00   1.00    1.00    --  108.00  32.00 -90.00   34
  5  \w    138.00 178.00   1.00    1.00    --  108.00 104.00-180.00   40
  6  \w    119.00 149.00   1.00    1.00    --   66.78 111.00-180.00   30
  7  \w    105.00 131.00   1.00    1.00    --  108.00 104.00-180.00   26
  8  \w     94.00 149.00   1.00    1.00    --   66.78 178.00-120.00   55
  9  \w    102.00 149.00   1.00    1.00    --   66.78 111.00 -60.00   47
 10  \w    106.00 178.00   1.00    1.00    --  108.00  32.00  60.00   72
 11  \w    106.00 148.00   1.00    1.00    --  108.00 -43.00  60.00   42
 12  \w     99.00 136.00   1.00    1.00    --  108.00 -65.00 -60.00   37
 13  \w     75.00 103.00   1.00    1.00    --  108.00 -43.00  60.00   28
 14  \w     76.00 139.00   1.00    1.00    --  108.00 -77.00 120.00   63
 15  \w     54.00 102.00   1.00    1.00    --  108.00  32.00  60.00   48
 16  \w     85.00 131.00   1.00    1.00    --  108.00  65.00 -30.00   46
 17  \w     80.00 147.00   1.00    1.00    --  108.00  65.00 -60.00   67
 18  \w     70.00 117.00   1.00    1.00    --  108.00  32.00 -90.00   47
 19  \w     38.00 142.00   1.00    1.00    --   66.78  61.00-120.00  104
 20  \w     73.00 150.00   1.00    1.00    --   66.78 178.00  30.00   77
 21  \w     34.00 146.00   1.00    1.00    --   66.78  30.00 -30.00  112
 22  \w     47.00 133.00   1.00    1.00    --  108.00 -65.00  90.00   86
 23  \w     57.00 119.00   1.00    1.00    --  108.00-119.00 -66.46   62
 24  \w     53.00  98.00   1.00    1.00    --  108.00-104.00  30.00   45
 25  \w     41.00 114.00   1.00    1.00    --  108.00-113.00 118.69   73
 26  \w     37.00  69.00   1.00    1.00    --  108.00 -43.00  60.00   32
 27  \w     26.00  60.00   1.00    1.00    --  108.00 -21.00  30.00   34
 28  \w     31.00  68.00   1.00    1.00    --  108.00 -65.00 -60.00   37
 29  \w     25.00 120.00   1.00    1.00    --  108.00 -77.00 -90.00   95
 30  \w     29.00  64.00   1.00    1.00    --   25.57 -77.00  90.00   35
 31  \w     -4.00  27.00   1.00    1.00    --   66.78 -45.00  30.00   31
 32  \w    -39.00  24.00   1.00    1.00    --   25.57 -77.00  90.00   63
 33  \w    -26.00  34.00   1.00    1.00    --   25.57 -77.00-120.00   60
 34  \w    -57.00 -29.00   1.00    1.00    --   25.57 -77.00-120.00   28
 35  \w     24.00 121.00   1.00    1.00    --   66.78  77.00   0.00   97
;
_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      0.0105456000
_diffrn_orient_matrix_UB_12      -0.1487939000
_diffrn_orient_matrix_UB_13      0.0342285000
_diffrn_orient_matrix_UB_21      -0.1011796000
_diffrn_orient_matrix_UB_22      -0.0508931000
_diffrn_orient_matrix_UB_23      -0.1178770000
_diffrn_orient_matrix_UB_31      0.1420953000
_diffrn_orient_matrix_UB_32      -0.0167670000
_diffrn_orient_matrix_UB_33      -0.0851304000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5108
_diffrn_reflns_theta_full        66.85
_diffrn_reflns_theta_max         66.85
_diffrn_reflns_theta_min         4.54
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0901P)^2^+0.3936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                2364
_reflns_number_total             3106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02042_si_002.cif
_cod_data_source_block           3m
_cod_original_cell_volume        890.83(15)
_cod_database_code               4035415
_chemical_oxdiff_formula         'C40 H36 N4 O10'
_reflns_odcompleteness_completeness 97.58
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C3(H3), C12(H12), C15(H15), C4(H4), C13(H13), C6(H6), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O27(H27)
;
_olex2_date_sample_data_collection 2017-12-01
_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.884