Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes
Zhang, Zhongyi; Hou, Zhong-Wei; Chen, Hao; Li, Pinhua; Wang, Lei; Green Chemistry 25 (2023) 3543–3548; doi:10.1039/D3GC00728F

data_7246541
_publ_section_title
;
 Electrochemical electrophilic bromination/spirocyclization of
 N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3543
_journal_page_last               3548
_journal_paper_doi               10.1039/D3GC00728F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.562(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6760(17)
_cell_length_b                   23.100(6)
_cell_length_c                   9.948(3)
_cell_measurement_reflns_used    3244
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.71
_cell_volume                     1529.3(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7387
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0175(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2181
_reflns_number_total             2683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3gc00728f2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7246540--7246541.cif.
;
_cod_original_cell_volume        1529.2(7)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7246541