Photocatalytic Unsymmetrical Coupling of 2-Substituted Quinolines: Synthesis and Evaluation of the Antiplasmodial Potential of β-Norbenzomorphan Frameworks
Kumar, Inder; Gupta, Shiv Shankar; Kumar, Rakesh; Kumar, Rohit; Agrawal, Prakhar; Sahal, Dinkar; Sharma, Upendra; ACS Sustainable Chemistry & Engineering  (2020) –; doi:10.1021/acssuschemeng.0c03415

data_4517960
_publ_section_title
;
 Photocatalytic Unsymmetrical Coupling of 2-Substituted Quinolines:
 Synthesis and Evaluation of the Antiplasmodial Potential of
 \b-Norbenzomorphan Frameworks
;
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_paper_doi               10.1021/acssuschemeng.0c03415
_journal_year                    2020
_chemical_formula_moiety         'C20 H18 N2'
_chemical_formula_sum            'C20 H18 N2'
_chemical_formula_weight         286.36
_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             2017-11-28
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                98.579(9)
_cell_angle_beta                 100.505(8)
_cell_angle_gamma                112.749(9)
_cell_formula_units_Z            2
_cell_length_a                   7.6889(7)
_cell_length_b                   9.7991(11)
_cell_length_c                   11.4575(12)
_cell_measurement_reflns_used    1295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8050
_cell_measurement_theta_min      5.0370
_cell_volume                     759.44(15)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     -9.00  91.00   1.00    1.00    --   25.57  57.00 -60.00  100
  2  \w    104.00 148.00   1.00    1.00    --   66.78 111.00 -90.00   44
  3  \w    149.00 178.00   1.00    3.50    --  108.00 104.00-180.00   29
  4  \w    104.00 140.00   1.00    3.50    --  108.00 104.00-180.00   36
  5  \w    102.00 178.00   1.00    3.50    --  108.00 104.00-150.00   76
  6  \w    123.00 149.00   1.00    1.00    --   66.78 111.00  60.00   26
  7  \w    127.00 165.00   1.00    3.50    --  108.00 104.00  60.00   38
  8  \w    121.00 168.00   1.00    3.50    --  108.00 104.00 150.00   47
  9  \w    135.00 178.00   1.00    3.50    --  108.00  43.00  90.00   43
 10  \w    122.00 147.00   1.00    3.50    --  108.00 -54.00 120.00   25
 11  \w     93.00 119.00   1.00    3.50    --  108.00 -54.00 120.00   26
 12  \w     84.00 152.00   1.00    3.50    --  108.00 -43.00  90.00   68
 13  \w     71.00 176.00   1.00    3.50    --  108.00  11.00 150.00  105
 14  \w    104.00 170.00   1.00    3.50    --  108.00 138.00  90.00   66
 15  \w     65.00  91.00   1.00    3.50    --  108.00  43.00  90.00   26
 16  \w     29.00  56.00   1.00    3.50    --  108.00 -43.00  90.00   27
 17  \w     42.00  70.00   1.00    3.50    --  108.00 -54.00 120.00   28
 18  \w     24.00 113.00   1.00    3.50    --  108.00-104.00  30.00   89
 19  \w     29.00 119.00   1.00    3.50    --  108.00-130.00 -37.00   90
 20  \w     35.00  94.00   1.00    1.00    --   66.78 -94.00-150.00   59
 21  \w     13.00 110.00   1.00    1.00    --   66.78-111.00  30.00   97
 22  \w     22.00 146.00   1.00    3.50    --  108.00 -89.00 120.00  124
 23  \w     35.00  88.00   1.00    1.00    --   25.57  57.00  60.00   53
 24  \w     15.00 149.00   1.00    1.00    --   66.78  30.00 -30.00  134
 25  \w     68.00 155.00   1.00    3.50    --  108.00  54.00-180.00   87
 26  \w     57.00  95.00   1.00    1.00    --   25.57  57.00-180.00   38
 27  \w     27.00 145.00   1.00    1.00    --   66.78  45.00-120.00  118
 28  \w     -4.00  31.00   1.00    1.00    --   25.57  57.00  60.00   35
 29  \w    -13.00 111.00   1.00    1.00    --   66.78 -45.00   0.00  124
 30  \w     -5.00  49.00   1.00    1.00    --   25.57  57.00-180.00   54
;
_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      0.0603886000
_diffrn_orient_matrix_UB_12      0.0219867000
_diffrn_orient_matrix_UB_13      -0.1193306000
_diffrn_orient_matrix_UB_21      0.0501063000
_diffrn_orient_matrix_UB_22      0.1712009000
_diffrn_orient_matrix_UB_23      0.0379456000
_diffrn_orient_matrix_UB_31      0.2110874000
_diffrn_orient_matrix_UB_32      0.0328721000
_diffrn_orient_matrix_UB_33      0.0647065000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4219
_diffrn_reflns_theta_full        66.91
_diffrn_reflns_theta_max         66.91
_diffrn_reflns_theta_min         5.04
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.552
_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    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0853P)^2^+0.0416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                2005
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sc0c03415_si_002.cif
_cod_data_source_block           usinb4_75_1
_cod_original_cell_volume        759.45(13)
_cod_database_code               4517960
_chemical_oxdiff_formula         'C40 H36 N4'
_reflns_odcompleteness_completeness 98.38
_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 Riding coordinates:
 N14(H14)
2.b Ternary CH refined with riding coordinates:
 C13(H13)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C20(H20), C3(H3), C18(H18), C4(H4), C19(H19), C5(H5)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2017-11-28
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.840