Domino [4+2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer N-Fused Polycycles.
Joshi, Dirgha Raj; Seo, Yohan; Heo, Yunkyung; Park, So-Hyeon; Lee, Yechan; Namkung, Wan; Kim, Ikyon; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01291

data_4038634
_publ_section_title
;
 Domino [4+2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer
 N-Fused Polycycles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01291
_journal_year                    2020
_chemical_formula_moiety         'C20 H12 Cl N O4'
_chemical_formula_sum            'C20 H12 Cl N O4'
_chemical_formula_weight         365.76
_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     dual
_audit_creation_date             2020-01-03
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:19:11 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                96.365(3)
_cell_angle_beta                 98.489(3)
_cell_angle_gamma                108.418(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2755(3)
_cell_length_b                   10.0566(4)
_cell_length_c                   14.2145(6)
_cell_measurement_reflns_used    7518
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0680
_cell_measurement_theta_min      2.7520
_cell_volume                     1094.34(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_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    -45.00  14.00   1.00    8.78    --  -11.20  81.00 -53.00   59
  2  \w    -36.00 -11.00   1.00    8.78    --  -11.20 -81.00-176.00   25
  3  \w    -33.00  45.00   1.00    8.78    --   11.83 -81.00-176.00   78
  4  \w    -66.00  21.00   1.00    8.78    --  -11.20 -77.00  90.00   87
  5  \w    -64.00  44.00   1.00    8.78    --   11.83 -77.00  30.00  108
  6  \w    -15.00  75.00   1.00    8.78    --   11.83  57.00  90.00   90
  7  \w    -13.00  86.00   1.00    8.78    --   11.83  38.00 -90.00   99
  8  \w    -20.00  53.00   1.00    8.78    --   11.83 -99.00 -90.00   73
  9  \w    -12.00  53.00   1.00    8.78    --   11.83 -99.00 150.00   65
 10  \w    -13.00  83.00   1.00    8.78    --   11.83  38.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0885396000
_diffrn_orient_matrix_UB_12      0.0405594000
_diffrn_orient_matrix_UB_13      0.0185740000
_diffrn_orient_matrix_UB_21      -0.0237841000
_diffrn_orient_matrix_UB_22      0.0325156000
_diffrn_orient_matrix_UB_23      0.0401046000
_diffrn_orient_matrix_UB_31      0.0086090000
_diffrn_orient_matrix_UB_32      -0.0546264000
_diffrn_orient_matrix_UB_33      0.0258044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light pink'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0967P)^2^+0.6182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4017
_reflns_number_total             4972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01291_si_002.cif
_cod_data_source_block           exp_1418
_cod_database_code               4038634
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C24 H12 Cl N O6'
_chemical_oxdiff_usercomment     DR-327
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C11(H11), C20(H20), C4(H4), C5(H5), C2(H2), C19(H19), C18(H18),
 C3(H3)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              3576
_shelx_hkl_checksum              47805
_shelx_fab_checksum              59047
_olex2_date_sample_data_collection 2020-01-02
_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 2.281
_oxdiff_exptl_absorpt_empirical_full_min 0.438