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_7063347
_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_moiety         'C11 H17 Br F3 N O2 S'
_chemical_formula_sum            'C11 H17 Br F3 N O2 S'
_chemical_formula_weight         364.22
_chemical_name_systematic
N-(1-(Bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)trifluoromethanesulfonamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-09 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                75.804(8)
_cell_angle_beta                 81.317(7)
_cell_angle_gamma                85.101(9)
_cell_formula_units_Z            2
_cell_length_a                   7.6458(8)
_cell_length_b                   8.4634(10)
_cell_length_c                   11.3756(8)
_cell_measurement_reflns_used    3071
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.2790
_cell_measurement_theta_min      2.7070
_cell_volume                     704.55(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -46.00  38.00   1.00   10.00    --  -16.00  72.00 -60.00   84
  2  \w   -106.00  10.00   1.00   10.00    --  -16.00 -53.00   0.00  116
  3  \w   -106.00 -34.00   1.00   10.00    --  -16.00 -53.00-180.00   72
  4  \w     41.00  67.00   1.00   10.00    --  -16.00  72.00 -60.00   26
  5  \w    -46.00  17.00   1.00   10.00    --  -16.00  72.00   0.00   63
  6  \w    -39.00  36.00   1.00   10.00    --  -16.00  35.00 -60.00   75
  7  \w    -63.00  47.00   1.00   10.00    --   17.00 -53.00 120.00  110
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6375
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.485
_exptl_absorpt_coefficient_mu    3.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0570P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1983
_reflns_number_total             2717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02582b2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7063345--7063349.cif.'
_cod_original_cell_volume        704.55(13)
_cod_database_code               7063347
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.654
_shelx_estimated_absorpt_t_min   0.576
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              61173
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;