Flow electrosynthesis of phosphinamides and phosphoramidates through P–N coupling
Boruah, Tribani; Ishizeki, Ren; Roldan, Alberto; Melen, Rebecca L.; Wirth, Thomas; Green Chemistry 26 (2024) 11722–11727; doi:10.1039/D4GC04450A

data_7249477
_publ_section_title
;
 Flow electrosynthesis of phosphinamides and phosphoramidates through P--N
 coupling
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              11722
_journal_page_last               11727
_journal_paper_doi               10.1039/D4GC04450A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C18 H16 N O P'
_chemical_formula_weight         293.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9837(12)
_cell_length_b                   9.6048(6)
_cell_length_c                   9.6892(7)
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.4880
_cell_measurement_theta_min      4.1500
_cell_volume                     1580.55(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7472
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.724
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.483
_diffrn_reflns_theta_min         3.832
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0371P)^2^+0.2447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_full    0.677
_reflns_Friedel_fraction_max     0.548
_reflns_number_gt                2320
_reflns_number_total             3179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc04450a2.cif
_cod_data_source_block           rm2343
_cod_depositor_comments
'Adding full bibliography for 7249476--7249480.cif.'
_cod_database_code               7249477
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              77514
_shelx_hkl_checksum              13059