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_7064038
_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         'C13 H21 F3 N2 O3 S'
_chemical_formula_sum            'C13 H21 F3 N2 O3 S'
_chemical_formula_weight         342.38
_chemical_melting_point          438.15
_chemical_name_systematic
N-((1S,2R,4R)-1-methyl-4-(prop-1-en-2-yl)-2-((trifluoromethyl)sulfonamido)cyclohexyl)acetamide
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-05 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.8486(8)
_cell_length_b                   10.8486(8)
_cell_length_c                   12.6716(12)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.17
_cell_volume                     1291.54(18)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0662
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24788
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.125
_diffrn_reflns_theta_min         2.168
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1915 before and 0.1061 after correction.
The Ratio of minimum to maximum transmission is 0.6987.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             540
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3283
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0578P)^2^+0.1926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                2736
_reflns_number_total             3283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02510a2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7064036--7064040.cif.'
_cod_original_cell_volume        1291.5(2)
_cod_database_code               7064038
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.834
_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), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              91212
_olex2_submission_special_instructions 'No special instructions were received'