Efficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles <i>via</i> manganese-catalyzed phosphinoenamination.
Sun, Runbo; Junpeng, Yang; Zhang, Zheng; Luo, Ruihang; Tang, Wentao; Liu, Xinyu; Liu, Xiaoyong; Ding, Anjun; Fu, Zhengjiang; Guo, Shengmei; Cai, Hu; Organic & biomolecular chemistry 22 (2024) 4993–5000; doi:10.1039/d4ob00489b

data_7159962
_publ_section_title
;
 Efficient synthesis of &#x3b1;-amino-vinylphosphine oxides from alkyl
 nitriles <i>via</i> manganese-catalyzed phosphinoenamination.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4993
_journal_page_last               5000
_journal_paper_doi               10.1039/d4ob00489b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.2(C16 H16 N O3 P)'
_chemical_formula_sum            'C H N O P'
_chemical_formula_weight         74.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-01 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.804(3)
_cell_angle_gamma                90
_cell_formula_units_Z            40
_cell_length_a                   22.033(2)
_cell_length_b                   13.718(2)
_cell_length_c                   10.1323(12)
_cell_measurement_reflns_used    3029
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.58
_cell_volume                     3034.1(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9104
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.779
_diffrn_reflns_theta_min         1.866
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0273 after correction.
The Ratio of minimum to maximum transmission is 0.9071.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             1480
_refine_diff_density_max         0.701
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0881
_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^)+(0.1305P)^2^+13.1102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.2628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2660
_reflns_number_total             3494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00489b2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7159962.cif.'
_cod_original_cell_volume        3034.0(7)
_cod_database_code               7159962
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00B(H00D), C00C(H00E), C00D(H00F), C00E(H00G), C00F(H00H),
 C00G(H00I), C00H(H00J), C00I(H00K), C00J(H00L), C00K(H00M)
2.b Idealised Me refined as rotating group:
 C00L(H00N,H00O,H00P)
;
_shelx_res_checksum              80598
_olex2_submission_special_instructions 'No special instructions were received'