Synthesis of 1,2,4-diazaphospholes <i>via</i> base-promoted cyclization reaction of hydrazonoyl chlorides and [Bu<sub>4</sub>N][P(SiCl<sub>3</sub>)<sub>2</sub>].
Wang, Xin; Luo, Hui; Yang, Bo; Li, Ming; Ma, Yong-Jun; Wang, Xi-Cun; Quan, Zheng-Jun; Organic & biomolecular chemistry 22 (2024) 7138–7142; doi:10.1039/d4ob01260g

data_7160094
_publ_section_title
;
 Synthesis of 1,2,4-diazaphospholes <i>via</i> base-promoted cyclization
 reaction of hydrazonoyl chlorides and
 [Bu<sub>4</sub>N][P(SiCl<sub>3</sub>)<sub>2</sub>].
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7138
_journal_page_last               7142
_journal_paper_doi               10.1039/d4ob01260g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H15 N2 P'
_chemical_formula_sum            'C20 H15 N2 P'
_chemical_formula_weight         314.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.548(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0016(4)
_cell_length_b                   11.8760(7)
_cell_length_c                   11.5703(8)
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      3.39
_cell_volume                     824.64(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4916
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.513
_diffrn_reflns_theta_min         3.395
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0290 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0330P)^2^+0.0707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.775
_reflns_Friedel_fraction_max     0.693
_reflns_number_gt                2740
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01260g2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160094.cif.'
_cod_database_code               7160094
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N)
;
_shelx_res_checksum              90515
_olex2_submission_special_instructions 'No special instructions were received'