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_7064037
_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 H23 Br N2 O2 S'
_chemical_formula_sum            'C18 H23 Br N2 O2 S'
_chemical_formula_weight         411.35
_chemical_melting_point          430.15
_chemical_name_systematic
1-((4-bromophenyl)sulfonyl)-2,3a-dimethyl-6-(prop-1-en-2-yl)-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             2024-07-08
_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                   9.3342(7)
_cell_length_b                   10.5853(8)
_cell_length_c                   19.8933(14)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      61.22
_cell_measurement_theta_min      4.45
_cell_volume                     1965.6(3)
_computing_cell_refinement       'SAINT V8.32B (BRUKER, 2016)'
_computing_data_collection       'Bruker APEX2'
_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      294.00
_diffrn_measured_fraction_theta_full 0.851
_diffrn_measured_fraction_theta_max 0.998
_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  0.0595
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.851
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25593
_diffrn_reflns_point_group_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         61.224
_diffrn_reflns_theta_min         4.445
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.939
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.4389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1422 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.5836.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       cube
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.048(7)
_refine_ls_extinction_coef       0.0054(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0659P)^2^+1.4421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.835
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2909
_reflns_number_total             3007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02510a2.cif
_cod_data_source_block           3e
_cod_depositor_comments
'Adding full bibliography for 7064036--7064040.cif.'
_cod_database_code               7064037
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.599
_shelx_estimated_absorpt_t_min   0.416
_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(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C18(H18), C17(H17)
3.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              82804
_olex2_submission_special_instructions 'No special instructions were received'