Concise synthesis of phosphonylated heteroarenes from nitroheteroarenes by dearomatization/elimination.
Meng, Li-Qin; Zhu, Xinrong; Xing, Qiaoyan; Zhang, Junliang; Wang, Huamin; Lin, Ying-Wu; Chemical communications (Cambridge, England) 61 (2025) 16810–16813; doi:10.1039/d5cc04735h

data_7135000
_publ_section_title
;
 Concise synthesis of phosphonylated heteroarenes from nitroheteroarenes
 by dearomatization/elimination.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16810
_journal_page_last               16813
_journal_paper_doi               10.1039/d5cc04735h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C21 H18 N O2 P'
_chemical_formula_sum            'C21 H18 N O2 P'
_chemical_formula_weight         347.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-07-08 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.652(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6354(7)
_cell_length_b                   11.6264(7)
_cell_length_c                   13.4546(8)
_cell_measurement_reflns_used    8741
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.558
_cell_measurement_theta_min      3.306
_cell_volume                     1819.35(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18662
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.662
_diffrn_reflns_theta_min         3.306
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8492.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0429P)^2^+0.6222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3661
_reflns_number_total             4142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04735h2.cif
_cod_data_source_block           250521_mlq_1
_cod_depositor_comments
'Adding full bibliography for 7134999--7135000.cif.'
_cod_database_code               7135000
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_res_checksum              68535
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'