Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N'-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite.
Kumar, Rakesh; Chaudhary, Sandeep; Kumar, Rohit; Upadhyay, Pooja; Sahal, Dinkar; Sharma, Upendra; The Journal of organic chemistry 83 (2018) 11552–11570; doi:10.1021/acs.joc.8b01520

data_4035181
_publ_section_title
;
 Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition
 of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct
 Access to Fused N,N'-Heterocycles with Promising Activity against a
 Drug-Resistant Malaria Parasite.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11552
_journal_page_last               11570
_journal_paper_doi               10.1021/acs.joc.8b01520
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         '2(C21 H19 N2 O3)'
_chemical_formula_sum            'C42 H38 N4 O6'
_chemical_formula_weight         694.76
_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                78.991(8)
_cell_angle_beta                 86.805(7)
_cell_angle_gamma                68.727(8)
_cell_formula_units_Z            1
_cell_length_a                   8.8716(8)
_cell_length_b                   9.7308(9)
_cell_length_c                   11.2518(11)
_cell_measurement_reflns_used    1924
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7340
_cell_measurement_theta_min      5.3500
_cell_volume                     888.40(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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -55.00   1.00   1.00    1.00    --   25.57 -37.00 120.00   56
  2  \w      3.00  78.00   1.00    1.00    --   25.57 -37.00 120.00   75
  3  \w     17.00 115.00   1.00    1.00    --   66.78-111.00  90.00   98
  4  \w     88.00 121.00   1.00    1.00    --  108.00-129.00 150.74   33
  5  \w     51.00 155.00   1.00    1.00    --  108.00 -89.00 120.00  104
  6  \w    129.00 167.00   1.00    1.00    --  108.00 -32.00  90.00   38
  7  \w     82.00 110.00   1.00    1.00    --  108.00-104.00 -60.00   28
  8  \w     66.00 149.00   1.00    1.00    --  108.00 -77.00 -60.00   83
  9  \w     55.00 119.00   1.00    1.00    --   25.57-178.00  90.00   64
 10  \w     47.00  87.00   1.00    1.00    --   66.78-111.00 -30.00   40
 11  \w     31.00 146.00   1.00    1.00    --  108.00 -54.00  90.00  115
 12  \w     66.00 109.00   1.00    1.00    --   25.57  77.00  90.00   43
 13  \w    111.00 146.00   1.00    1.00    --   66.78 111.00  90.00   35
 14  \w    115.00 144.00   1.00    1.00    --   66.78 111.00 150.00   29
 15  \w    105.00 158.00   1.00    1.00    --  108.00 104.00 120.00   53
 16  \w    119.00 157.00   1.00    1.00    --  108.00 104.00 150.00   38
 17  \w    104.00 178.00   1.00    1.00    --  108.00 104.00  60.00   74
 18  \w    148.00 178.00   1.00    1.00    --  108.00 138.00  30.00   30
 19  \w    103.00 150.00   1.00    1.00    --   66.78 111.00-120.00   47
 20  \w    140.00 170.00   1.00    1.00    --  108.00 138.00-180.00   30
 21  \w    104.00 148.00   1.00    1.00    --  108.00 104.00-180.00   44
 22  \w     93.00 119.00   1.00    1.00    --  108.00 138.00-180.00   26
 23  \w     33.00 171.00   1.00    1.00    --  108.00  21.00-180.00  138
 24  \w     99.00 144.00   1.00    1.00    --  108.00 138.00  30.00   45
 25  \w    103.00 161.00   1.00    1.00    --  108.00 104.00  90.00   58
 26  \w     46.00 121.00   1.00    1.00    --  108.00 -32.00  90.00   75
 27  \w     46.00  81.00   1.00    1.00    --  108.00-129.00 150.74   35
 28  \w     -3.00 109.00   1.00    1.00    --   66.78 -45.00 120.00  112
 29  \w     34.00  64.00   1.00    1.00    --   25.57  77.00  90.00   30
 30  \w    -11.00  32.00   1.00    1.00    --   25.57  77.00  90.00   43
 31  \w    -17.00 136.00   1.00    1.00    --   66.78  15.00  90.00  153
 32  \w     29.00 126.00   1.00    1.00    --   66.78  77.00 -90.00   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      0.0118285000
_diffrn_orient_matrix_UB_12      0.0515059000
_diffrn_orient_matrix_UB_13      0.1192513000
_diffrn_orient_matrix_UB_21      0.0682116000
_diffrn_orient_matrix_UB_22      -0.1648871000
_diffrn_orient_matrix_UB_23      0.0651200000
_diffrn_orient_matrix_UB_31      0.1730339000
_diffrn_orient_matrix_UB_32      -0.0054085000
_diffrn_orient_matrix_UB_33      -0.0315975000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5098
_diffrn_reflns_theta_full        66.89
_diffrn_reflns_theta_max         66.89
_diffrn_reflns_theta_min         5.35
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.564
_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    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1498P)^2^+0.6115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2597
_reflns_number_gt                2451
_reflns_number_total             3135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01520_si_004.cif
_cod_data_source_block           usrknb3_61_1a_rt_cu
_cod_original_cell_volume        888.40(14)
_cod_database_code               4035181
_chemical_oxdiff_formula         'C42 H38 N4 O6'
_reflns_odcompleteness_completeness 98.46
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22), C4AA(H4AA)
2.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC)
;
_olex2_date_sample_data_collection 2017-11-30
_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.833