ZnCl2-Mediated Stereo- and Chemoselective Synthesis of Vinylphosphonates
Kaboudin, Babak; Moradi, Atieh; Esfandiari, Hesam; Daliri, Payam; Kazemi, Foad; Yanai, Hikaru; Aoyama, Hiroshi; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00037G

data_7158543
_publ_section_title
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 ZnCl2-Mediated Stereo- and Chemoselective Synthesis of Vinylphosphonates
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00037G
_journal_year                    2022
_chemical_formula_moiety         'C19 H20 N O4 P'
_chemical_formula_sum            'C19 H20 N O4 P'
_chemical_formula_weight         357.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-18
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
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2021-07-17 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
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_cell_angle_alpha                102.427(3)
_cell_angle_beta                 90.106(3)
_cell_angle_gamma                113.697(3)
_cell_formula_units_Z            2
_cell_length_a                   8.872(2)
_cell_length_b                   10.452(3)
_cell_length_c                   10.957(3)
_cell_measurement_reflns_used    3876
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.52
_cell_volume                     904.1(4)
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Bruker SMART APEX II Ultra'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_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  0.0241
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9044
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         1.913
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0684 before and 0.0344 after correction.
The Ratio of minimum to maximum transmission is 0.8678.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.221
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0457P)^2^+0.6442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3310
_reflns_number_total             4093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00037g2.cif
_cod_data_source_block           p-1
_cod_original_cell_volume        904.2(4)
_cod_database_code               7158543
_publcif_datablock.id            {6a67144f-ef50-4748-b6d1-20533f7cf274}
_shelx_shelxl_version_number     2016/6
_audit_contact_letter
;
 ?
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_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
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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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C11(H11), C15(H15), C5(H5), C12(H12), C7(H7), C13(H13),
 C6(H6), C14(H14)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
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_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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