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_7064040
_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_absolute_configuration unk
_chemical_formula_moiety         'C18 H23 Cl N2 O2 S'
_chemical_formula_sum            'C18 H23 Cl N2 O2 S'
_chemical_formula_weight         366.914
_chemical_melting_point          409.15
_chemical_name_systematic
1-((4-chlorophenyl)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'
_symmetry_Int_Tables_number      19
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-07-05
_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                   9.3126(6)
_cell_length_b                   10.5891(8)
_cell_length_c                   19.6462(15)
_cell_measurement_reflns_used    8810
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.19
_cell_volume                     1937.4(2)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.00
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.9980
_diffrn_reflns_Laue_measured_fraction_max 0.9980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20056
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9966
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.18
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1815 before and 0.0824 after correction.
The Ratio of minimum to maximum transmission is 0.8291.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       prism
_exptl_crystal_F_000             777.489
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.3945
_refine_diff_density_min         -0.4243
_refine_diff_density_rms         0.0817
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_d_res_high            0.7702
_refine_ls_d_res_low             9.3213
_refine_ls_goodness_of_fit_ref   1.0268
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0268
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.7592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              25
_reflns_limit_l_min              -25
_reflns_number_gt                2883
_reflns_number_total             4433
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5nj02510a2.cif
_cod_data_source_block           3d
_cod_depositor_comments
'Adding full bibliography for 7064036--7064040.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7064040
_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
: with sigma of 0.05 and sigma for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C5(H5), C3(H3)
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:
 C17(H17), C18(H18), C15(H15), C14(H14)
3.d X=CH2 refined with riding coordinates:
 C11(H11a,H11b)
3.e Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C8(H8a,H8b,H8c), C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'