Stereoselective synthesis of vinylphosphonates through aromatic aza-Claisen rearrangement of α-aminophosphonates.
Kaboudin, Babak; Ghashghaee, Mojtaba; Fukaya, Haruhiko; Yanai, Hikaru; Chemical communications (Cambridge, England) 59 (2023) 7076–7079; doi:10.1039/d3cc01669b

data_7131632
_publ_section_title
;
 Stereoselective synthesis of vinylphosphonates through aromatic
 aza-Claisen rearrangement of &#x3b1;-aminophosphonates.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7076
_journal_page_last               7079
_journal_paper_doi               10.1039/d3cc01669b
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C20 H25 Cl N O3 P'
_chemical_formula_sum            'C20 H25 Cl N O3 P'
_chemical_formula_weight         393.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-15 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                75.0040(10)
_cell_angle_beta                 89.6230(10)
_cell_angle_gamma                65.8280(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6173(2)
_cell_length_b                   9.9762(2)
_cell_length_c                   13.0120(3)
_cell_measurement_reflns_used    9096
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.44
_cell_volume                     979.49(4)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker SMART APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX II ULTRA'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm  '
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44212
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_min         1.631
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9627.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5995
_refine_ls_number_restraints     185
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0419P)^2^+0.3660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5582
_reflns_number_total             5995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01669b2.cif
_cod_data_source_block           x-ray-1
_cod_depositor_comments
'Adding full bibliography for 7131632--7131633.cif.'
_cod_database_code               7131632
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.927
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 P1, C7, C14, O2, C5, O1, C12, Cl1, C9, O3, C10, N1, C19, C3, C13, C4, C1, C16,
  C20, C2, C6, C11, C17, C15, C18, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              5972
_shelx_hkl_checksum              73013
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGEN MicroMounts in  perfluoropolyether oil'
_olex2_submission_special_instructions 'No special instructions were received'