Electrochemical phosphorylation of α,β-unsaturated carboxylic acids <i>via</i> decarboxylative cross-coupling reaction.
Zhang, Zhaoqi; Shen, Yirui; Zhao, Yufen; Wu, Ju; Chemical communications (Cambridge, England) 61 (2025) 12034–12037; doi:10.1039/d5cc03160e

data_7134809
_publ_section_title
;
 Electrochemical phosphorylation of &#x3b1;,&#x3b2;-unsaturated carboxylic
 acids <i>via</i> decarboxylative cross-coupling reaction.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12034
_journal_page_last               12037
_journal_paper_doi               10.1039/d5cc03160e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C20 H15 O P'
_chemical_formula_sum            'C20 H15 O P'
_chemical_formula_weight         302.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-06-03 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7526(9)
_cell_length_b                   16.3049(15)
_cell_length_c                   16.4854(14)
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      5.36
_cell_volume                     3159.0(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            78595
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.350
_diffrn_reflns_theta_min         5.360
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.517
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6192
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1560 before and 0.0968 after correction.
The Ratio of minimum to maximum transmission is 0.8222.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.016
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0546P)^2^+1.6604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2279
_reflns_number_total             2899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03160e2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7134808--7134809.cif.'
_cod_database_code               7134809
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C1(H1), C9(H9), C4(H4), C16(H16), C8(H8), C11(H11), C3(H3),
 C20(H20), C2(H2), C10(H10), C19(H19), C17(H17), C18(H18)
;
_shelx_res_checksum              87491
_shelx_hkl_checksum              45394
_olex2_submission_special_instructions 'No special instructions were received'