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_7134808
_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 H16 Cl O P'
_chemical_formula_sum            'C20 H16 Cl O P'
_chemical_formula_weight         338.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-04-28 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            4
_cell_length_a                   8.9934(2)
_cell_length_b                   9.8046(2)
_cell_length_c                   18.7482(4)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      5.09
_cell_volume                     1653.15(6)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16353
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_min         5.090
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5152
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.6841.
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    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0460P)^2^+0.1123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0734
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2915
_reflns_number_total             2952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03160e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7134808--7134809.cif.'
_cod_database_code               7134808
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.802
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
;
_shelx_res_checksum              39995
_shelx_hkl_checksum              53280
_olex2_submission_special_instructions 'No special instructions were received'