Catalytic three-component carboamination of unactivated alkenes with primary sulfonamides
Zhang, Ying; Li, Kai-Dian; Zhou, Chang-Quan; Xing, Zhi-Xi; Huang, Huan-Ming; Green Chemistry 26 (2024) 10434–10440; doi:10.1039/D4GC02879A

data_7249236
_publ_section_title
;
 Catalytic three-component carboamination of unactivated alkenes with
 primary sulfonamides
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              10434
_journal_page_last               10440
_journal_paper_doi               10.1039/D4GC02879A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C20 H33 N O4 S'
_chemical_formula_sum            'C20 H33 N O4 S'
_chemical_formula_weight         383.53
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-02-26 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.511(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1602(6)
_cell_length_b                   9.3426(4)
_cell_length_c                   17.4352(8)
_cell_measurement_reflns_used    7446
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      56.13
_cell_measurement_theta_min      3.53
_cell_volume                     2137.03(17)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24408
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.053
_diffrn_reflns_theta_min         3.531
_diffrn_source_current           1.14
_diffrn_source_power             0.07966319999999999
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6117
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0902 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8143.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0023(8)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0860P)^2^+2.2145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.1829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3443
_reflns_number_total             4376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc02879a2.cif
_cod_data_source_block           zpd1_0m
_cod_depositor_comments          'Adding full bibliography for 7249236.cif.'
_cod_database_code               7249236
_shelx_shelxl_version_number     2018/3
_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:
 C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00E(H00F,H00G), C00J(H00L,H00M)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C008(H008), C00A(H00C), C00B(H00D), C00D(H00E)
2.d Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K), C00K(H00N,H00O,H00P), C00L(H00Q,H00R,H00S), C00M(H00T,
 H00U,H00V), C00O(H00W,H00X,H00Y), C00P(H00Z,H,HA), C00Q(H00,HB,HC)
;
_shelx_res_checksum              63854
_shelx_hkl_checksum              29429
_olex2_submission_special_instructions 'No special instructions were received'