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_7244196
_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         'C17 H14 Br N'
_chemical_formula_sum            'C17 H14 Br N'
_chemical_formula_weight         312.20
_chemical_name_common            SS1-246RF1
_chemical_name_systematic        1-allyl-3-bromo-2-phenyl-1H-indole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-23 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2567(5)
_cell_length_b                   19.7843(11)
_cell_length_c                   8.8668(5)
_cell_measurement_reflns_used    9099
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.21
_cell_volume                     1448.42(14)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS 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  0.0631
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40196
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         3.851
_exptl_absorpt_coefficient_mu    2.823
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1152 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(6)
_refine_ls_extinction_coef       0.059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0372P)^2^+0.4683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                3045
_reflns_number_total             3972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08588c2.cif
_cod_data_source_block           shelx
_cod_database_code               7244196
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.602
_shelx_estimated_absorpt_t_max   0.630
_shelx_res_checksum              49966