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_7064039
_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         'C19 H23 F3 N2 O2 S'
_chemical_formula_sum            'C19 H23 F3 N2 O2 S'
_chemical_formula_weight         400.45
_chemical_melting_point          411.15
_chemical_name_systematic
2,3a-dimethyl-6-(prop-1-en-2-yl)-1-((4-(trifluoromethyl)phenyl)sulfonyl)-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-06-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5856(4)
_cell_length_b                   10.5654(4)
_cell_length_c                   20.1903(8)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      62.15
_cell_measurement_theta_min      4.38
_cell_volume                     2044.79(14)
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_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      294.0
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25188
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.681
_diffrn_reflns_theta_min         4.380
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.788
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.4391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1582 before and 0.0812 after correction.
The Ratio of minimum to maximum transmission is 0.5838.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.038(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.0986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2798
_reflns_number_total             3251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02510a2.cif
_cod_data_source_block           3g
_cod_depositor_comments
'Adding full bibliography for 7064036--7064040.cif.'
_cod_database_code               7064039
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.840
_shelx_estimated_absorpt_t_min   0.621
_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. Restrained distances
 F1-C18 \\sim F1A-C18
 with sigma of 0.02
 C18-F3 \\sim C18-F3A
 with sigma of 0.02
 C18-F2 \\sim C18-F2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq: with sigma of 0.009 and sigma for terminal atoms of 0.018
Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F2)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C16(H16), C17(H17)
5.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C19(H19A,H19B,H19C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              16047
_olex2_submission_special_instructions 'No special instructions were received'