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_4035179
_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_absolute_configuration unk
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.36
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                115.199(13)
_cell_angle_beta                 93.554(8)
_cell_angle_gamma                98.472(9)
_cell_formula_units_Z            1
_cell_length_a                   5.3633(4)
_cell_length_b                   9.1569(12)
_cell_length_c                   9.3749(10)
_cell_measurement_reflns_used    1030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.3830
_cell_measurement_theta_min      5.4510
_cell_volume                     408.03(9)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.948
_diffrn_measured_fraction_theta_max 0.948
_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     24.00  56.00   1.00    1.00    --   25.57  77.00  90.00   32
  2  \w     59.00 102.00   1.00    1.00    --   25.57  77.00  90.00   43
  3  \w    117.00 149.00   1.00    1.00    --   66.78 111.00  60.00   32
  4  \w    147.00 175.00   1.00    6.50    --  108.00 104.00   0.00   28
  5  \w    144.00 174.00   1.00    6.50    --  108.00 104.00 -60.00   30
  6  \w    145.00 173.00   1.00    6.50    --  108.00 104.00 -90.00   28
  7  \w    121.00 158.00   1.00    6.50    --  108.00 104.00-120.00   37
  8  \w    105.00 159.00   1.00    6.50    --  108.00 104.00 -30.00   54
  9  \w    106.00 137.00   1.00    6.50    --  108.00 104.00 -90.00   31
 10  \w    109.00 139.00   1.00    6.50    --  108.00 104.00 -60.00   30
 11  \w    103.00 148.00   1.00    1.00    --   66.78 111.00   0.00   45
 12  \w    103.00 142.00   1.00    6.50    --  108.00 104.00   0.00   39
 13  \w     67.00 145.00   1.00    1.00    --   66.78 178.00 150.00   78
 14  \w     64.00 111.00   1.00    1.00    --   25.57 178.00  30.00   47
 15  \w     21.00  97.00   1.00    1.00    --   25.57  57.00-180.00   76
 16  \w     37.00 148.00   1.00    1.00    --   66.78 -15.00 -90.00  111
 17  \w     90.00 172.00   1.00    6.50    --  108.00 -32.00-180.00   82
 18  \w     93.00 145.00   1.00    6.50    --  108.00 -77.00-120.00   52
 19  \w     85.00 135.00   1.00    6.50    --  108.00 -65.00 -60.00   50
 20  \w     75.00 110.00   1.00    6.50    --  108.00-104.00 -60.00   35
 21  \w     69.00 109.00   1.00    6.50    --  108.00-104.00-150.00   40
 22  \w     57.00  94.00   1.00    1.00    --   66.78 -45.00-120.00   37
 23  \w     53.00  80.00   1.00    6.50    --  108.00 -77.00-120.00   27
 24  \w     45.00  71.00   1.00    6.50    --  108.00 -32.00-180.00   26
 25  \w     35.00  61.00   1.00    6.50    --  108.00-104.00-150.00   26
 26  \w     24.00  71.00   1.00    6.50    --  108.00-104.00 -60.00   47
 27  \w     34.00  67.00   1.00    6.50    --  108.00 -65.00 -60.00   33
 28  \w     45.00 102.00   1.00    6.50    --  108.00-104.00  60.00   57
 29  \w     79.00 109.00   1.00    6.50    --  108.00-104.00 120.00   30
 30  \w     38.00  94.00   1.00    1.00    --   66.78 -94.00 120.00   56
 31  \w     33.00  99.00   1.00    1.00    --   66.78 -45.00  90.00   66
 32  \w     27.00 166.00   1.00    6.50    --  108.00  21.00  90.00  139
 33  \w     29.00  69.00   1.00    6.50    --  108.00-104.00 120.00   40
 34  \w      0.00  28.00   1.00    1.00    --   66.78 -94.00 120.00   28
 35  \w     -9.00  28.00   1.00    1.00    --   66.78 -45.00  90.00   37
 36  \w    -14.00  20.00   1.00    1.00    --   25.57  77.00  90.00   34
 37  \w    -16.00  32.00   1.00    1.00    --   66.78 -15.00 -90.00   48
 38  \w      0.00  30.00   1.00    1.00    --   66.78 -45.00-120.00   30
;
_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      0.0413486000
_diffrn_orient_matrix_UB_12      -0.1776468000
_diffrn_orient_matrix_UB_13      -0.0916433000
_diffrn_orient_matrix_UB_21      -0.0413451000
_diffrn_orient_matrix_UB_22      -0.0306030000
_diffrn_orient_matrix_UB_23      0.1469301000
_diffrn_orient_matrix_UB_31      -0.2873826000
_diffrn_orient_matrix_UB_32      -0.0583500000
_diffrn_orient_matrix_UB_33      -0.0604051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2054
_diffrn_reflns_theta_full        66.69
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_min         5.67
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_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    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             170
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.273
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1521
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.1037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2701
_refine_ls_wR_factor_ref         0.2971
_reflns_number_gt                1335
_reflns_number_total             1521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01520_si_006.cif
_cod_data_source_block           urknb5_22_2_rt_cu
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        408.04(8)
_cod_original_formula_moiety     '0.5(C22 H16 N2 O)'
_cod_original_formula_sum        'C11 H8 N O0.50'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     162.18
_cod_database_code               4035179
_chemical_oxdiff_formula         'C22 H16 N2 O1'
_reflns_odcompleteness_completeness 93.81
_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:
 C0AA(H0AA)
2.b Aromatic/amide H refined with riding coordinates:
 C5AA(H5AA), C1AA(H1AA), C4AA(H4AA), C0BA(H0BA), C9AA(H9AA), C6BA(H6BA),
 C4BA(H4BA), C1BA(H1BA), C2BA(H2BA), C2(H2), C5BA(H5BA), C8BA(H8BA), C9BA(H9BA),
  C5(H5), C1(H1)
;
_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 25.262
_oxdiff_exptl_absorpt_empirical_full_min 0.323