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_7062216
_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         'C21 H19 Br N2 O2 Si'
_chemical_formula_sum            'C21 H19 Br N2 O2 Si'
_chemical_formula_weight         439.38
_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             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                114.403(8)
_cell_angle_beta                 100.557(6)
_cell_angle_gamma                92.945(7)
_cell_formula_units_Z            2
_cell_length_a                   9.7796(7)
_cell_length_b                   10.0750(10)
_cell_length_c                   11.8548(8)
_cell_measurement_reflns_used    3047
_cell_measurement_temperature    239.95(10)
_cell_measurement_theta_max      26.3120
_cell_measurement_theta_min      1.9330
_cell_volume                     1035.10(16)
_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      239.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_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     25.00  54.00   1.00    5.00    --  -15.44  33.00 113.00   29
  2  \w    -52.00  38.00   1.00    5.00    --   17.94 -33.00 -45.00   90
  3  \w     12.00  88.00   1.00    5.00    --   17.94  33.00 113.00   76
  4  \w    -27.00   4.00   1.00    5.00    --  -15.44 -77.00-180.00   31
  5  \w    -88.00 -39.00   1.00    5.00    --  -15.44-178.00 120.00   49
  6  \w    -39.00   0.00   1.00    5.00    --  -15.44 -77.00 -90.00   39
  7  \w    -82.00 -56.00   1.00    5.00    --  -15.44 178.00-180.00   26
  8  \w    -33.00   1.00   1.00    5.00    --  -15.44 -77.00 120.00   34
  9  \w    -19.00  31.00   1.00    5.00    --   17.94 -99.00 120.00   50
;
_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      -0.0465047000
_diffrn_orient_matrix_UB_12      0.0512164000
_diffrn_orient_matrix_UB_13      0.0236800000
_diffrn_orient_matrix_UB_21      0.0535148000
_diffrn_orient_matrix_UB_22      0.0589115000
_diffrn_orient_matrix_UB_23      0.0153845000
_diffrn_orient_matrix_UB_31      -0.0229893000
_diffrn_orient_matrix_UB_32      -0.0024074000
_diffrn_orient_matrix_UB_33      -0.0612295000
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9117
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.936
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83915
_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    1.410
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0474P)^2^+0.0140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2951
_reflns_number_total             4166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05257a2.cif
_cod_data_source_block           shi_4953_elba_auto
_cod_depositor_comments
'Adding full bibliography for 7062215--7062217.cif.'
_cod_original_cell_volume        1035.10(15)
_cod_database_code               7062216
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N2Si1O2Br1
_chemical_oxdiff_usercomment     AZD_35_FR5-7
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.683
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_shelx_res_checksum              20063
_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.836