1,3-Dipolar cycloaddition of cycloimmonium salts and 4-(trimethylsilyl)-3-butyn-2-one to access new functionalized indolizines with potential cytostatic activity
Zubaş, Andreea; Ghinet, Alina; Shova, Sergiu; Bîcu, Elena; New Journal of Chemistry 47 (2023) 3758–3772; doi:10.1039/D2NJ05257A

data_7062217
_publ_section_title
;
 1,3-Dipolar cycloaddition of cycloimmonium salts and
 4-(trimethylsilyl)-3-butyn-2-one to access new functionalized indolizines
 with potential cytostatic activity
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3758
_journal_page_last               3772
_journal_paper_doi               10.1039/D2NJ05257A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C22 H12 Br2 N2 O'
_chemical_formula_sum            'C22 H12 Br2 N2 O'
_chemical_formula_weight         480.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-14 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0194(10)
_cell_length_b                   7.5074(6)
_cell_length_c                   35.454(3)
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      21.2730
_cell_measurement_theta_min      1.8680
_cell_volume                     3731.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -47.00   5.00   1.00    5.00    --  -15.44 112.00 -28.00   52
  2  \w     21.00  46.00   1.00    5.00    --   17.94-112.00-121.00   25
  3  \w    -88.00 -39.00   1.00    5.00    --  -15.44-178.00   0.00   49
  4  \w     -9.00  30.00   1.00    5.00    --   17.94  77.00 150.00   39
  5  \w      2.00  82.00   1.00    5.00    --   17.94  57.00-150.00   80
  6  \w     -7.00   4.00   1.00    5.00    --   17.94  77.00-120.00   11
;
_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      -0.0320585000
_diffrn_orient_matrix_UB_12      -0.0249054000
_diffrn_orient_matrix_UB_13      -0.0145558000
_diffrn_orient_matrix_UB_21      -0.0161630000
_diffrn_orient_matrix_UB_22      0.0893703000
_diffrn_orient_matrix_UB_23      -0.0012843000
_diffrn_orient_matrix_UB_31      0.0356205000
_diffrn_orient_matrix_UB_32      0.0180603000
_diffrn_orient_matrix_UB_33      -0.0136660000
_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  0.0923
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16286
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.852
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.00044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0618
_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^)+3.0554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1966
_reflns_number_total             3293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05257a2.cif
_cod_data_source_block           shi_4957_elba_autored
_cod_depositor_comments
'Adding full bibliography for 7062215--7062217.cif.'
_cod_database_code               7062217
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N1O2Br1
_chemical_oxdiff_usercomment     43_FR16
_shelx_estimated_absorpt_t_max   0.670
_shelx_estimated_absorpt_t_min   0.355
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21)
;
_shelx_res_checksum              6279
_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 3.112
_oxdiff_exptl_absorpt_empirical_full_min 0.595