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_4033663
_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         'C25 H30 N3 O2 S, C F3 O3 S'
_chemical_formula_sum            'C26 H30 F3 N3 O5 S2'
_chemical_formula_weight         585.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.7223(16)
_cell_length_b                   11.0633(8)
_cell_length_c                   10.7204(9)
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3610
_cell_measurement_theta_min      3.8890
_cell_volume                     2813.5(4)
_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 8.0267
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_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     22.00  71.00   1.00   45.00    --   16.83  57.00-180.00   49
  2  \w     23.00  81.00   1.00   45.00    --   16.83  57.00   0.00   58
  3  \w    -10.00  74.00   1.00   45.00    --   16.83  77.00 -90.00   84
  4  \w    -74.00 -47.00   1.00   45.00    --  -16.04-178.00-150.00   27
  5  \w    -88.00 -63.00   1.00   45.00    --  -16.04-178.00  30.00   25
  6  \w     -9.00  29.00   1.00   45.00    --   16.83  77.00  90.00   38
;
_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      0.0288053000
_diffrn_orient_matrix_UB_12      0.0163569000
_diffrn_orient_matrix_UB_13      -0.0054291000
_diffrn_orient_matrix_UB_21      -0.0065325000
_diffrn_orient_matrix_UB_22      0.0368892000
_diffrn_orient_matrix_UB_23      -0.0521730000
_diffrn_orient_matrix_UB_31      -0.0045985000
_diffrn_orient_matrix_UB_32      0.0499064000
_diffrn_orient_matrix_UB_33      0.0402440000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16716
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.522
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48745
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.52(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5872
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1320P)^2^+0.1350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2183
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.776
_reflns_Friedel_fraction_max     0.591
_reflns_number_gt                4375
_reflns_number_total             5872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01919_si_001.cif
_cod_data_source_block           exp_2642
_cod_database_code               4033663
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C26 H30 F3 N3 O5 S2'
_chemical_oxdiff_usercomment     Raed_1737
_reflns_odcompleteness_completeness 99.67
_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 Riding coordinates:
 N008(H008)
2.b Ternary CH refined with riding coordinates:
 C00J(H00J)
2.c Secondary CH2 refined with riding coordinates:
 C00F(H00a,H00b), C00R(H00f,H00g), C00T(H00h,H00i)
2.d Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00P(H00P), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z)
2.e Idealised Me refined as rotating group:
 C00G(H00c,H00d,H00e), C00X(H00k,H00l,H00m), C010(H01a,H01b,H01c), C011(H01d,
 H01e,H01f), C012(H01g,H01h,H01i)
;
_olex2_date_sample_data_collection 2019-04-28
_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.735