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_7062215
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-14 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.699(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   9.5866(6)
_cell_length_b                   20.1420(7)
_cell_length_c                   31.2607(17)
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    160.2(5)
_cell_measurement_theta_max      21.3820
_cell_measurement_theta_min      2.0210
_cell_volume                     6015.9(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      160.2(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -18.00   7.00   1.00   30.00    --  -15.29  21.00-140.00   25
  2  \w    -46.00  46.00   1.00   30.00    --   17.79 -21.00  52.00   92
  3  \w     29.00  73.00   1.00   30.00    --   17.79  21.00-140.00   44
  4  \w    -86.00 -40.00   1.00   30.00    --  -15.29-178.00-150.00   46
  5  \w      1.00  58.00   1.00   30.00    --   17.79  57.00 -90.00   57
  6  \w      3.00  28.00   1.00   30.00    --   17.79  77.00 -90.00   25
;
_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      -0.0354273000
_diffrn_orient_matrix_UB_12      0.0067904000
_diffrn_orient_matrix_UB_13      0.0185674000
_diffrn_orient_matrix_UB_21      0.0623931000
_diffrn_orient_matrix_UB_22      -0.0065431000
_diffrn_orient_matrix_UB_23      0.0131220000
_diffrn_orient_matrix_UB_31      0.0190630000
_diffrn_orient_matrix_UB_32      0.0339269000
_diffrn_orient_matrix_UB_33      -0.0011948000
_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  0.1261
_diffrn_reflns_av_unetI/netI     0.1827
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32300
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.022
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05806
_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    1.455
_exptl_crystal_description       plate
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         10608
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1662
_refine_ls_R_factor_gt           0.0808
_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^)+(0.0520P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1794
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5592
_reflns_number_total             10608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05257a2.cif
_cod_data_source_block           shi_4973_elba_auto
_cod_depositor_comments
'Adding full bibliography for 7062215--7062217.cif.'
_cod_database_code               7062215
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N3O2
_chemical_oxdiff_usercomment     'AZD_35 Fr13'
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.676
_reflns_odcompleteness_completeness 99.80
_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. Uiso/Uaniso restraints and constraints
Uanis(C7C) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
Uanis(N1C) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C17A(H17A), C19A(H19A), C20A(H20A),
 C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C17B(H17B), C19B(H19B), C20B(H20B),
 C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C), C17C(H17C), C19C(H19C), C20C(H20C)
3.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C16A(H16A,
 H16B,H16C), C10B(H10D,H10E,H10F), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F),
 C16B(H16D,H16E,H16F), C10C(H10G,H10H,H10I), C11C(H11G,H11H,H11I), C12C(H12G,
 H12H,H12I), C16C(H16G,H16H,H16I)
;
_shelx_res_checksum              37705
_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 10.516
_oxdiff_exptl_absorpt_empirical_full_min 0.718