Skeletal rearrangements and structures of halosulfonamidation products of caryophyllene
Moskalik, Mikhail Yu.; Garagan, Ivan A.; Myasnikova, Valentina S.; Borodina, Tatyana N.; Shainyan, Bagrat A.; New Journal of Chemistry 50 (2026) 1935–1942; doi:10.1039/D5NJ03976B

data_7064318
_publ_section_title
;
 Skeletal rearrangements and structures of halosulfonamidation products of
 caryophyllene
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1935
_journal_page_last               1942
_journal_paper_doi               10.1039/D5NJ03976B
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C24 H32 F3 I N2 O2 S'
_chemical_formula_sum            'C24 H32 F3 I N2 O2 S'
_chemical_formula_weight         596.47
_chemical_melting_point          466.6
_chemical_name_systematic
N-(6-iodo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((4-(trifluoromethyl)phenyl)sulfonyl)acetimidamide
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-02-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-13 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.162(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5276(11)
_cell_length_b                   11.5823(12)
_cell_length_c                   10.7820(12)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.59
_cell_volume                     1309.4(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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0518
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27070
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.896
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.347
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1715 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.5915.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichlormetan-methanol'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.255
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Flack x determined using 1839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5668
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.1300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                4641
_reflns_number_total             5668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03976b2.cif
_cod_data_source_block           4h
_cod_database_code               7064318
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.725
_shelx_estimated_absorpt_t_min   0.499
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(F2) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C6(H6), C3(H3), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C4(H4A,H4B), C9(H9B,H9C), C8(H8A,H8B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C18(H18), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C)
;
_shelx_res_checksum              64491
_olex2_submission_special_instructions 'No special instructions were received'