Electrochemical synthesis of phosphorylated oxazolines from <i>N</i>-allylamides.
Thondur, Jagadeesh Reddy; Gowda, Punith S.; Sharada, Duddu S.; Satyanarayana, Gedu; Chemical communications (Cambridge, England) 61 (2025) 14717–14720; doi:10.1039/d5cc03899e

data_7134909
_publ_section_title
;
 Electrochemical synthesis of phosphorylated oxazolines from
 <i>N</i>-allylamides.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14717
_journal_page_last               14720
_journal_paper_doi               10.1039/d5cc03899e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C28 H24 N O2 P'
_chemical_formula_sum            'C28 H24 N O2 P'
_chemical_formula_weight         437.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-06-23 deposited with the CCDC.	2025-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.181(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0125(10)
_cell_length_b                   12.501(2)
_cell_length_c                   15.039(3)
_cell_measurement_reflns_used    5137
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.333
_cell_measurement_theta_min      2.724
_cell_volume                     1123.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-V Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25702
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.105
_diffrn_reflns_theta_min         2.123
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0781 after correction.
The Ratio of minimum to maximum transmission is 0.8186.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4708
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0389P)^2^+0.0195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                3487
_reflns_number_total             4708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03899e2.cif
_cod_data_source_block           mo_gs_jr_p4
_cod_depositor_comments          'Adding full bibliography for 7134909.cif.'
_cod_original_cell_volume        1123.8(4)
_cod_database_code               7134909
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C28(H28), C27(H27), C26(H26), C10(H10), C11(H11),
 C12(H12), C5(H5), C6(H6), C24(H24), C25(H25), C18(H18), C19(H19), C14(H14),
 C15(H15), C16(H16), C8(H8), C9(H9)
;
_shelx_res_checksum              53021
_shelx_hkl_checksum              14091
_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'