Sequencing [4+1]-Cycloaddition and Aza-Michael Addition Reactions: A Diastereoselective Cascade for the Rapid Access of Pyrido[2',1':2,3]/Thiazolo[2',3':2,3]imidazo[1,5-a]quinolone Scaffolds as Potential Antibacterial and Anticancer Motifs.
Srinivasulu, Vunnam; Khanfar, Monther A. A.; Omar, Hany A.; ElAwady, Raafat; Sieburth, Scott McN; Sebastian, Anusha; Zaher, Dana M.; Al Marzooq, Farah; Hersi, Fatema; Al-Tel, Taleb H; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01919

data_4033664
_publ_section_title
;
 Sequencing [4+1]-Cycloaddition and Aza-Michael Addition Reactions: A
 Diastereoselective Cascade for the Rapid Access of
 Pyrido[2',1':2,3]/Thiazolo[2',3':2,3]imidazo[1,5-a]quinolone Scaffolds as
 Potential Antibacterial and Anticancer Motifs.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01919
_journal_year                    2019
_chemical_formula_moiety         'C31 H32 N3 O2 S, C F3 O3 S'
_chemical_formula_sum            'C32 H32 F3 N3 O5 S2'
_chemical_formula_weight         659.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-29
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.234(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1269(5)
_cell_length_b                   26.0079(10)
_cell_length_c                   11.7877(7)
_cell_measurement_reflns_used    3705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3390
_cell_measurement_theta_min      3.7870
_cell_volume                     3179.6(3)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8584
_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    -19.00  29.00   1.00   10.00    --  -16.20  57.00  90.00   48
  2  \w    -73.00 -18.00   1.00   10.00    --  -16.20 -57.00 -60.00   55
  3  \w    -21.00  23.00   1.00   10.00    --  -16.20 -99.00   0.00   44
  4  \w    -33.00  43.00   1.00   10.00    --  -16.20  57.00-150.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0023127000
_diffrn_orient_matrix_UB_12      0.0207552000
_diffrn_orient_matrix_UB_13      -0.0397507000
_diffrn_orient_matrix_UB_21      -0.0009869000
_diffrn_orient_matrix_UB_22      -0.0176857000
_diffrn_orient_matrix_UB_23      -0.0461891000
_diffrn_orient_matrix_UB_31      -0.0683116000
_diffrn_orient_matrix_UB_32      -0.0004463000
_diffrn_orient_matrix_UB_33      -0.0213555000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15787
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         7392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+1.7950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5177
_reflns_number_total             7392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01919_si_002.cif
_cod_data_source_block           exp_2301
_cod_database_code               4033664
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C32 H32 F3 N3 O5 S2'
_chemical_oxdiff_usercomment     Raed-1980
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00S(H00C,H00D), C00V(H00E,H00F), C00W(H00G,H00H), C015(H01D,
 H01E)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00K(H00K), C00P(H00P), C00R(H00R), C00T(H00T), C00U(H00U),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012), C013(H013), C016(H016),
 C017(H017)
2.c Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C018(H01F,H01G,H01H), C019(H01I,H01J,H01K)
;
_olex2_date_sample_data_collection 2018-07-09
_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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.871