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_7064322
_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         'C18 H31 I N2 O2 S'
_chemical_formula_sum            'C18 H31 I N2 O2 S'
_chemical_formula_weight         466.41
_chemical_melting_point          437.6
_chemical_name_systematic
'N-(9-iodo-4,4,8-trimethyltricyclo[6.3.1.0^2,5]dodecan-1-yl)-N'- (methylsulfonyl)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             2025-02-28
_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                 98.025(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2188(10)
_cell_length_b                   15.8711(18)
_cell_length_c                   18.129(3)
_cell_measurement_reflns_used    9175
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.61
_cell_volume                     2056.7(5)
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_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  0.1484
_diffrn_reflns_av_unetI/netI     0.2944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42760
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.816
_diffrn_reflns_theta_min         2.269
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.671
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1656 before and 0.0859 after correction.
The Ratio of minimum to maximum transmission is 0.7124.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ?hloroform-dietil ether'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.584
_refine_diff_density_min         -1.110
_refine_diff_density_rms         0.165
_refine_ls_abs_structure_details
;
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         8548
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0410P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5447
_reflns_number_total             8548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03976b2.cif
_cod_data_source_block           5a
_cod_database_code               7064322
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.434
_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(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
Uanis(O1) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(O101) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9), C102(H102), C2(H2), C5(H5), C105(H105), C109(H109)
3.b Secondary CH2 refined with riding coordinates:
 C112(H11C,H11D), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B),
 C11(H11A,H11B), C12(H12A,H12B), C103(H10C,H10D), C106(H10E,H10F), C107(H10G,
 H10H), C110(H11N,H11O), C111(H11P,H11Q)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N101(H101)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C114(H11E,H11F,H11G), C118(H11H,H11I,H11J), C113(H11K,H11L,H11M),
 C115(H11R,H11S,H11T), C117(H11U,H11V,H11W), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              53705
_olex2_submission_special_instructions 'No special instructions were received'