DMSO–allyl bromide: a mild and efficient reagent for atom economic one-pot N-allylation and bromination of 2°-aryl amines, 2-aryl aminoamides, indoles and 7-aza indoles
Smile, Suresh Snoxma; Novanna, Motakatla; Kannadasan, Sathananthan; Shanmugam, Ponnusamy; RSC Advances 12 (2022) 1834–1839; doi:10.1039/D1RA08588C

data_7244197
_publ_section_title
;
 DMSO--allyl bromide: a mild and efficient reagent for atom economic
 one-pot N-allylation and bromination of 2\%-aryl amines, 2-aryl
 aminoamides, indoles and 7-aza indoles
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1834
_journal_page_last               1839
_journal_paper_doi               10.1039/D1RA08588C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C23 H21 Br N2 O'
_chemical_formula_sum            'C23 H21 Br N2 O'
_chemical_formula_weight         421.33
_chemical_name_common            SS1-280R
_chemical_name_systematic
N-allyl-5-bromo-N-phenyl-2-(p-tolylamino)benzamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-08-05 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.312(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.519(3)
_cell_length_b                   9.117(2)
_cell_length_c                   20.975(6)
_cell_measurement_reflns_used    3029
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.02
_cell_measurement_theta_min      2.44
_cell_volume                     2011.5(9)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker axs kappa apex2 Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0965
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15037
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.942
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (bruker, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2016
_reflns_number_total             3742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08588c2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7244197
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.684
_shelx_estimated_absorpt_t_max   0.748
_shelx_res_checksum              23102