Halosulfonamidation of camphene: chemo and stereoselectivity, rearrangement, solvent interception, heterocyclization
Moskalik, Mikhail Yu.; Garagan, Ivan A.; Shainyan, Bagrat A.; Yarovaya, Olga I.; Ganin, Anton S.; Astakhova, Vera V.; Sterkhova, Irina V.; Zinchenko, Sergey V.; Salakhutdinov, Nariman F.; Radzhabov, Amirbek D.; New Journal of Chemistry 48 (2024) 13506–13513; doi:10.1039/D4NJ02582B

data_7063345
_publ_section_title
;
 Halosulfonamidation of camphene: chemo and stereoselectivity,
 rearrangement, solvent interception, heterocyclization
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13506
_journal_page_last               13513
_journal_paper_doi               10.1039/D4NJ02582B
_journal_volume                  48
_journal_year                    2024
_chemical_formula_sum            'C13 H20 Br F3 N2 O2 S'
_chemical_formula_weight         405.28
_chemical_melting_point          428
_chemical_name_systematic
N-(3-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)-N'-((trifluoromethyl)sulfonyl)acetamidamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-03-16 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
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_cell_angle_gamma                90
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_cell_measurement_reflns_used    125
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
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_cell_volume                     1688.7(10)
_computing_cell_refinement       'Bruker SAINT'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.992
_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
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_diffrn_reflns_av_unetI/netI     0.1276
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       14
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_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            60138
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.321
_diffrn_reflns_theta_min         2.245
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4649
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       plate
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'Re-crystallisation from solvent: acetonitrile'
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         5035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1864
_refine_ls_R_factor_gt           0.0929
_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^)+(0.1339P)^2^+1.6510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2417
_refine_ls_wR_factor_ref         0.2728
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2579
_reflns_number_total             5035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02582b2.cif
_cod_data_source_block           mo_Astakhova_A61_0m
_cod_depositor_comments
'Adding full bibliography for 7063345--7063349.cif.'
_cod_original_cell_volume        1688.8(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063345
_shelx_estimated_absorpt_t_min   0.423
_shelx_estimated_absorpt_t_max   0.746
_shelxl_version_number           2013-3
_shelx_res_checksum              95288