Chemo-, regio-, and stereoselective heterocyclization of sulfonamides and d-limonene with solvent interception
Moskalik, Mikhail Yu.; Myasnikova, Valentina S.; Astakhova, Vera V.; Borodina, Tatyana N.; Zinchenko, Sergey V.; Shainyan, Bagrat A.; New Journal of Chemistry 49 (2025) 18097–18102; doi:10.1039/D5NJ02510A

data_7064036
_publ_section_title
;
 Chemo-, regio-, and stereoselective heterocyclization of sulfonamides and
 d-limonene with solvent interception
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18097
_journal_page_last               18102
_journal_paper_doi               10.1039/D5NJ02510A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C18 H24 N2 O2 S'
_chemical_formula_sum            'C18 H24 N2 O2 S'
_chemical_formula_weight         332.45
_chemical_melting_point          375.15
_chemical_name_systematic
2,3a-dimethyl-1-(phenylsulfonyl)-6-(prop-1-en-2-yl)-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-07-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-06 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.780(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5960(14)
_cell_length_b                   11.0118(14)
_cell_length_c                   9.5399(15)
_cell_measurement_reflns_used    3871
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.63
_cell_measurement_theta_min      2.37
_cell_volume                     902.0(2)
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.32B (BRUKER, 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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9843
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.884
_diffrn_reflns_theta_min         2.137
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.8722.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       needle
_exptl_crystal_F_000             356
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0577P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                2429
_reflns_number_total             3648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02510a2.cif
_cod_data_source_block           3c
_cod_depositor_comments
'Adding full bibliography for 7064036--7064040.cif.'
_cod_database_code               7064036
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.902
_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:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C18(H18), C17(H17)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              77191
_olex2_submission_special_instructions 'No special instructions were received'