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_4035182
_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         'C26 H19 N3 O3'
_chemical_formula_sum            'C26 H19 N3 O3'
_chemical_formula_weight         421.44
_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             2018-04-09
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                82.831(5)
_cell_angle_beta                 88.793(5)
_cell_angle_gamma                78.374(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5284(5)
_cell_length_b                   10.4453(7)
_cell_length_c                   10.9147(6)
_cell_measurement_reflns_used    3231
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0340
_cell_measurement_theta_min      4.0840
_cell_volume                     1055.69(11)
_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    'ShelXT (Sheldrick, 2015)'
_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     -7.00  98.00   1.00    1.00    --   25.69  57.00 -30.00  105
  2  \w     96.00 145.00   1.00    1.00    --   66.85  50.00 -60.00   49
  3  \w    145.00 172.00   1.00    5.00    --  108.00  77.00-120.00   27
  4  \w    151.00 177.00   1.00    5.00    --  108.00  54.00-150.00   26
  5  \w    126.00 176.00   1.00    5.00    --  108.00  54.00 -60.00   50
  6  \w    136.00 174.00   1.00    5.00    --  108.00 138.00-180.00   38
  7  \w    115.00 141.00   1.00    5.00    --  108.00  54.00-150.00   26
  8  \w    108.00 149.00   1.00    1.00    --   66.85 111.00-120.00   41
  9  \w     89.00 122.00   1.00    5.00    --  108.00 138.00-180.00   33
 10  \w     84.00 110.00   1.00    5.00    --  108.00  77.00-120.00   26
 11  \w     70.00  96.00   1.00    5.00    --  108.00  54.00-150.00   26
 12  \w     60.00 178.00   1.00    5.00    --  108.00  32.00 -90.00  118
 13  \w     98.00 136.00   1.00    5.00    --  108.00 -65.00  30.00   38
 14  \w    121.00 146.00   1.00    5.00    --  108.00 -77.00 120.00   25
 15  \w     66.00 109.00   1.00    5.00    --  108.00 -77.00 120.00   43
 16  \w     39.00  82.00   1.00    5.00    --  108.00 -65.00  30.00   43
 17  \w     25.00 108.00   1.00    5.00    --  108.00-104.00 120.00   83
 18  \w     16.00 114.00   1.00    1.00    --   66.85-111.00 -30.00   98
 19  \w     91.00 117.00   1.00    5.00    --  108.00-120.00-133.95   26
 20  \w     40.00 147.00   1.00    5.00    --  108.00 -77.00-150.00  107
 21  \w     63.00 163.00   1.00    5.00    --  108.00  32.00   0.00  100
 22  \w    102.00 144.00   1.00    1.00    --   66.85 111.00 150.00   42
 23  \w    112.00 178.00   1.00    5.00    --  108.00 138.00 120.00   66
 24  \w    149.00 177.00   1.00    5.00    --  108.00  54.00 150.00   28
 25  \w     95.00 151.00   1.00    5.00    --  108.00 138.00 150.00   56
 26  \w     89.00 132.00   1.00    5.00    --  108.00  54.00 150.00   43
 27  \w     39.00 122.00   1.00    1.00    --   66.85  63.00   0.00   83
 28  \w     68.00 122.00   1.00    5.00    --  108.00  54.00 -60.00   54
 29  \w     32.00  76.00   1.00    1.00    --   66.85  50.00 -60.00   44
 30  \w     27.00 126.00   1.00    1.00    --   66.85  37.00-120.00   99
 31  \w     35.00 130.00   1.00    1.00    --   66.85  63.00  90.00   95
 32  \w      7.00  92.00   1.00    1.00    --   66.85 -77.00 150.00   85
 33  \w    -10.00  87.00   1.00    1.00    --   25.69  57.00 120.00   97
 34  \w     26.00  64.00   1.00    5.00    --  108.00-120.00-133.95   38
 35  \w      4.00  99.00   1.00    1.00    --   25.69  57.00-150.00   95
;
_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      0.0157001000
_diffrn_orient_matrix_UB_12      0.1367421000
_diffrn_orient_matrix_UB_13      0.0298857000
_diffrn_orient_matrix_UB_21      0.1024634000
_diffrn_orient_matrix_UB_22      -0.0656702000
_diffrn_orient_matrix_UB_23      0.1073125000
_diffrn_orient_matrix_UB_31      0.1284620000
_diffrn_orient_matrix_UB_32      -0.0034267000
_diffrn_orient_matrix_UB_33      -0.0884786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6266
_diffrn_reflns_theta_full        66.83
_diffrn_reflns_theta_max         66.83
_diffrn_reflns_theta_min         4.08
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.413
_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    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0633P)^2^+0.1875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                3230
_reflns_number_total             3702
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01520_si_005.cif
_cod_data_source_block           usrknb5_68_1_rt_cu
_cod_original_cell_volume        1055.70(11)
_cod_database_code               4035182
_chemical_oxdiff_formula         'C52 H38 N6 O6'
_reflns_odcompleteness_completeness 98.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C15(H15), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C12(H12), C32(H32), C10(H10), C22(H22), C9(H9), C18(H18),
 C8(H8), C28(H28), C30(H30), C31(H31), C21(H21), C20(H20), C29(H29), C19(H19)
;
_olex2_date_sample_data_collection 2018-04-04
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.861