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_4035180
_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         '4(C21 H20 N2 O3)'
_chemical_formula_sum            'C84 H80 N8 O12'
_chemical_formula_weight         1393.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-23
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            1
_cell_length_a                   5.7505(2)
_cell_length_b                   9.7182(4)
_cell_length_c                   32.0971(15)
_cell_measurement_reflns_used    1834
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6360
_cell_measurement_theta_min      5.3120
_cell_volume                     1793.73(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    -41.00  64.00   1.00    1.00    --   25.69 -57.00 -90.00  105
  2  \w     73.00 137.00   1.00    2.00    --   66.85  45.00  60.00   64
  3  \w    118.00 158.00   1.00   15.00    --  108.00 104.00 -60.00   40
  4  \w    124.00 177.00   1.00   15.00    --  108.00 104.00-120.00   53
  5  \w    108.00 140.00   1.00    2.00    --   66.85 149.00 -61.00   32
  6  \w    101.00 146.00   1.00    2.00    --   66.85 113.00-127.00   45
  7  \w    102.00 170.00   1.00   15.00    --  108.00 104.00 -90.00   68
  8  \w    121.00 171.00   1.00   15.00    --  108.00 -21.00 -60.00   50
  9  \w     85.00 110.00   1.00   15.00    --  108.00-104.00  30.00   25
 10  \w     43.00  77.00   1.00   15.00    --  108.00-104.00  30.00   34
 11  \w     33.00 110.00   1.00   15.00    --  108.00 -21.00 -60.00   77
 12  \w     33.00 122.00   1.00    2.00    --   66.85  61.00-180.00   89
;
_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      -0.0529076000
_diffrn_orient_matrix_UB_12      -0.0145746000
_diffrn_orient_matrix_UB_13      -0.0468657000
_diffrn_orient_matrix_UB_21      0.0223227000
_diffrn_orient_matrix_UB_22      0.1569071000
_diffrn_orient_matrix_UB_23      -0.0052702000
_diffrn_orient_matrix_UB_31      0.2617697000
_diffrn_orient_matrix_UB_32      -0.0163519000
_diffrn_orient_matrix_UB_33      -0.0090411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            3561
_diffrn_reflns_theta_full        66.86
_diffrn_reflns_theta_max         66.86
_diffrn_reflns_theta_min         5.32
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_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     236
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0843P)^2^+0.1086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                2446
_reflns_number_total             2616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01520_si_003.cif
_cod_data_source_block           usrknb3_61_1b_rt_cu
_cod_original_cell_volume        1793.75(13)
_cod_database_code               4035180
_chemical_oxdiff_formula         'C84 H80 N8 O12'
_reflns_odcompleteness_completeness 98.13
_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:
 C14(H14), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C3AA(H3AA), C6(H6), C8(H8), C12(H12), C13(H13), C17(H17), C19(H19), C20(H20),
 C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_date_sample_data_collection 2016-06-21
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.719