Catalytic aminomethylative etherification of <i>N</i>-allenamides with <i>N</i>,<i>O</i>-acetals enabled by Lewis/Brønsted acid catalysis.
Zhang, Tao; Ji, Danqing; Sun, Jiangtao; Organic & biomolecular chemistry 21 (2023) 3340–3344; doi:10.1039/d3ob00363a

data_7159270
_publ_section_title
;
 Catalytic aminomethylative etherification of <i>N</i>-allenamides with
 <i>N</i>,<i>O</i>-acetals enabled by Lewis/Br&#xf8;nsted acid catalysis.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3340
_journal_page_last               3344
_journal_paper_doi               10.1039/d3ob00363a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C32 H33 Br N2 O3 S'
_chemical_formula_weight         605.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-14 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6485(3)
_cell_length_b                   13.5819(4)
_cell_length_c                   22.0979(6)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.86
_cell_measurement_theta_min      2.83
_cell_volume                     2895.82(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16873
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.857
_diffrn_reflns_theta_min         3.323
_exptl_absorpt_coefficient_mu    1.904
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0262
_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^)+(0.0322P)^2^+0.3867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0694
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                4959
_reflns_number_total             5124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00363a2.cif
_cod_data_source_block           20190415ZH_CZ_JDQ3187_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159269--7159270.cif.'
_cod_database_code               7159270
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.818
_shelx_estimated_absorpt_t_max   0.863
_shelx_res_checksum              3588