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_7063958
_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         'C34 H35 N O P, Br, 2(C3 H6 O)'
_chemical_formula_sum            'C40 H47 Br N O3 P'
_chemical_formula_weight         700.66
_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                99.944(2)
_cell_angle_beta                 92.981(2)
_cell_angle_gamma                106.741(2)
_cell_formula_units_Z            4
_cell_length_a                   10.3050(4)
_cell_length_b                   17.3919(7)
_cell_length_c                   21.4516(13)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      3.61
_cell_volume                     3605.2(3)
_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 0.870
_diffrn_measured_fraction_theta_max 0.889
_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  0.0577
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.870
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            128694
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         1.723
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.222
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1316 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.6524.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.494
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     839
_refine_ls_number_reflns         18756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0484P)^2^+3.3777P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14383
_reflns_number_total             18756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02552d2.cif
_cod_data_source_block           dp280_0m
_cod_depositor_comments
'Adding full bibliography for 7063950--7063958.cif.'
_cod_database_code               7063958
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.599
_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.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C4(H4), C64(H64)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C57(H57A,H57B), C63(H63A,H63B), C71(H71A,H71B), C76(H76A,
 H76B), C2(H2A,H2B), C27(H27A,H27B), C33(H33A,H33B), C47(H47A,H47B), C53(H53A,
 H53B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C13(H13), C16(H16), C23(H23), C24(H24),
 C32(H32), C36(H36), C44(H44), C45(H45), C46(H46), C50(H50), C55(H55), C58(H58),
  C59(H59), C65(H65), C70(H70), C78(H78), C3(H3), C8(H8), C10(H10), C15(H15),
 C20(H20), C21(H21), C22(H22), C34(H34), C40(H40), C41(H41), C42(H42), C43(H43),
  C52(H52), C56(H56), C60(H60), C61(H61), C62(H62), C68(H68), C72(H72), C74(H74)
2.d Idealised Me refined as rotating group:
 C75(H75A,H75B,H75C), C69(H69A,H69B,H69C), C39(H39A,H39B,H39C), C79(H79A,H79B,
 H79C), C19(H19A,H19B,H19C), C37(H37A,H37B,H37C), C9(H9A,H9B,H9C), C77(H77A,
 H77B,H77C), C31(H31A,H31B,H31C), C67(H67A,H67B,H67C)
;
_shelx_res_checksum              50737
_olex2_submission_special_instructions 'No special instructions were received'