Nitrilation of carboxylic acids by P<sup>III</sup>/P<sup>V</sup>-catalysis.
Ali, Siraj Z.; Manno, Nicolás A; Shen, Jeff; Schenker, Alessia; Lipshultz, Jeffrey M.; White, Nicholas A.; Radosevich, Alexander T.; Chemical science 16 (2025) 16145–16150; doi:10.1039/d5sc05216e

data_1575308
_publ_section_title
;
 Nitrilation of carboxylic acids by
 P<sup>III</sup>/P<sup>V</sup>-catalysis.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              16145
_journal_page_last               16150
_journal_paper_doi               10.1039/d5sc05216e
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H11 O2, C8 H12 N'
_chemical_formula_sum            'C19 H23 N O2'
_chemical_formula_weight         297.38
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2hzdpl
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-01-02 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.83723(9)
_cell_length_b                   11.91509(19)
_cell_length_c                   23.6848(4)
_cell_measurement_reflns_used    9797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.44
_cell_measurement_theta_min      3.73
_cell_volume                     1647.30(5)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36101
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.429
_diffrn_reflns_theta_min         3.732
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_correction_T_min  0.6218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1391 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0448P)^2^+0.3976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3411
_reflns_number_total             3494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05216e2.cif
_cod_data_source_block           p23183
_cod_depositor_comments          'Adding full bibliography for 1575308.cif.'
_cod_original_cell_volume        1647.31(5)
_cod_database_code               1575308
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.818
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              51563