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_7134999
_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 H16 N O2 P'
_chemical_formula_sum            'C21 H16 N O2 P'
_chemical_formula_weight         345.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-08 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                99.774(12)
_cell_angle_beta                 106.774(13)
_cell_angle_gamma                100.943(13)
_cell_formula_units_Z            2
_cell_length_a                   8.710(3)
_cell_length_b                   10.081(4)
_cell_length_c                   11.048(4)
_cell_measurement_reflns_used    8811
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      27.559
_cell_measurement_theta_min      2.533
_cell_volume                     885.5(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Ius3.0'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20138
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_min         1.983
_diffrn_source                   'Ius X-ray source'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              Ius
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1550 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.9111.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.061
_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     226
_refine_ls_number_reflns         4081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0368P)^2^+0.5056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3362
_reflns_number_total             4081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04735h2.cif
_cod_data_source_block           241012_txy_1_6
_cod_depositor_comments
'Adding full bibliography for 7134999--7135000.cif.'
_cod_original_cell_volume        885.6(6)
_cod_database_code               7134999
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'