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_7063348
_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 H22 Br N2 O2 S'
_chemical_formula_weight         350.29
_chemical_melting_point          417.3
_chemical_name_systematic
(Z)-N-(2-(bromomethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-yl)-N'-(methylsulfonyl)acetimidamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
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_atom_sites_solution_secondary   difmap
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_audit_update_record
;
2022-06-08 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
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_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.205
_diffrn_reflns_theta_min         2.515
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    2.655
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5861
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       plate
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'Re-crystallisation from solvent: dimethyl ether'
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_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.2170
_refine_ls_R_factor_gt           0.0839
_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^)+(0.0889P)^2^+0.9183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.2111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             4684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02582b2.cif
_cod_data_source_block           mo_Garagan_102_20_0m
_cod_depositor_comments
'Adding full bibliography for 7063345--7063349.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7063348
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.457
_shelx_estimated_absorpt_t_max   0.901
_shelx_res_checksum              11721