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_7063954
_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_formula_moiety         'C33 H33 N P, Br'
_chemical_formula_sum            'C33 H33 Br N P'
_chemical_formula_weight         554.48
_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             2024-12-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-17 deposited with the CCDC.	2025-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                79.652(7)
_cell_angle_beta                 79.737(6)
_cell_angle_gamma                66.268(8)
_cell_formula_units_Z            2
_cell_length_a                   10.348(2)
_cell_length_b                   12.478(3)
_cell_length_c                   12.502(2)
_cell_measurement_reflns_used    9061
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.57
_cell_volume                     1443.7(5)
_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      120.00
_diffrn_measured_fraction_theta_full 0.644
_diffrn_measured_fraction_theta_max 0.629
_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  0.1053
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.644
_diffrn_reflns_Laue_measured_fraction_max 0.629
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36039
_diffrn_reflns_point_group_measured_fraction_full 0.644
_diffrn_reflns_point_group_measured_fraction_max 0.629
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         1.667
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.500
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1247 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.6802.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.401
_exptl_crystal_size_min          0.306
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0203P)^2^+8.8390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             3957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02552d2.cif
_cod_data_source_block           dp282_0m
_cod_depositor_comments
'Adding full bibliography for 7063950--7063958.cif.'
_cod_database_code               7063954
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.657
_shelx_estimated_absorpt_t_min   0.532
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C23)
Uanis(C28) = Uanis(C25)
Uanis(C10) = Uanis(C19)
Uanis(C25) = Uanis(C28) = Uanis(C1) = Uanis(C21)
Uanis(C9) = Uanis(C11) = Uanis(C7) = Uanis(C27)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C33(H33)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C18(H18A,H18B), C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C32(H32)
3.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              30309
_shelx_fab_checksum              31174
_olex2_submission_special_instructions 'No special instructions were received'