Radical-induced denitration of <i>N</i>-(<i>p</i>-nitrophenyl)propiolamides coupled with dearomatization: access to phosphonylated/trifluoromethylated azaspiro[4.5]-trienones.
Mo, Kangdong; Zhou, Xiaocong; Wu, Ju; Zhao, Yufen; Chemical communications (Cambridge, England) 58 (2021) 1306–1309; doi:10.1039/d1cc05724c

data_7129627
_publ_section_title
;
 Radical-induced denitration of
 <i>N</i>-(<i>p</i>-nitrophenyl)propiolamides coupled with
 dearomatization: access to phosphonylated/trifluoromethylated
 azaspiro[4.5]-trienones.
;
_journal_issue                   9
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1306
_journal_page_last               1309
_journal_paper_doi               10.1039/d1cc05724c
_journal_volume                  58
_journal_year                    2021
_chemical_formula_moiety         'C20 H22 N O5 P'
_chemical_formula_sum            'C20 H22 N O5 P'
_chemical_formula_weight         387.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2827p9
_audit_creation_date             2021-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4032(2)
_cell_length_b                   12.0627(4)
_cell_length_c                   19.3355(6)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      71.89
_cell_measurement_theta_min      4.33
_cell_volume                     1949.85(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      303.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43223
_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         72.263
_diffrn_reflns_theta_min         4.326
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.702
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             925
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0805P)^2^+0.4923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3223
_reflns_number_total             3836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05724c2.cif
_cod_data_source_block           123
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H N O P'
_cod_original_formula_weight         74.00
_cod_original_formula_moiety         '0.16(C20 H22 N O5 P)'
_cod_original_formula_units_Z            25
_cod_database_code               7129627
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00H,H00N), C00P(H00O,H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00E), C00Q(H00Q,H00R,H00S), C00R(H00T,H00U,H00V)
;
_shelx_res_checksum              1452
_shelx_hkl_checksum              90023
_olex2_submission_special_instructions 'No special instructions were received'