Diastereospecific cyclization of 3-arylidene-1-pyrrolinium salts containing an alkyltriarylphosphonium fragment: a path to the synthesis of new pyrrolizidine derivatives
Rizbayeva, Tanzilya; Smolobochkin, Andrey; Gazizov, Almir; Babaeva, Olga; Lyubina, Anna; Sapunova, Anastasiia; Voloshina, Alexandra; Gerasimova, Daria; Burilov, Alexander; Pudovik, Michail; New Journal of Chemistry 49 (2025) 14718–14727; doi:10.1039/D5NJ02552D

data_7063956
_publ_section_title
;
 Diastereospecific cyclization of 3-arylidene-1-pyrrolinium salts
 containing an alkyltriarylphosphonium fragment: a path to the synthesis
 of new pyrrolizidine derivatives
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14718
_journal_page_last               14727
_journal_paper_doi               10.1039/D5NJ02552D
_journal_volume                  49
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Br, C32 H30 F N P'
_chemical_formula_sum            'C32 H30 Br F N P'
_chemical_formula_weight         558.45
_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             2025-02-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-27 deposited with the CCDC.	2025-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                67.137(7)
_cell_angle_beta                 73.761(7)
_cell_angle_gamma                79.434(7)
_cell_formula_units_Z            2
_cell_length_a                   10.376(2)
_cell_length_b                   12.439(3)
_cell_length_c                   14.218(3)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.40
_cell_volume                     1617.6(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.597
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1263 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.7909.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.149
_refine_diff_density_max         3.027
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6370
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.1140
_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^)+(0.0904P)^2^+20.3310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2768
_refine_ls_wR_factor_ref         0.2846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5330
_reflns_number_total             6370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02552d2.cif
_cod_data_source_block           dp317_0m
_cod_depositor_comments
'Adding full bibliography for 7063950--7063958.cif.'
_cod_original_cell_volume        1617.5(7)
_cod_database_code               7063956
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.517
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C2)
3. Rigid body (RIGU) restrains
 C32, C33, C29, C30, C28, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C2(H2A,H2B), C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C27(H27), C32(H32), C24(H24), C33(H33), C29(H29), C14(H14),
 C18(H18), C12(H12), C23(H23), C26(H26), C25(H25), C19(H19), C20(H20), C17(H17),
  C15(H15), C21(H21), C30(H30), C31(H31), C9(H9)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              80385
_shelx_fab_checksum              31267
_olex2_submission_special_instructions 'No special instructions were received'