Regioselective radical arylation: silver-mediated synthesis of 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides.
Hou, Hong; Xu, Yue; Yang, Haibo; Yan, Chaoguo; Shi, Yaocheng; Zhu, Shaoqun; Organic & biomolecular chemistry 17 (2019) 8175–8184; doi:10.1039/c9ob01585j

data_7157034
_publ_section_title
;
 Regioselective radical arylation: silver-mediated synthesis of
 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8175
_journal_page_last               8184
_journal_paper_doi               10.1039/c9ob01585j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C31 H28 N O2 P'
_chemical_formula_sum            'C31 H28 N O2 P'
_chemical_formula_weight         477.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2019-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                89.785(5)
_cell_angle_beta                 77.673(5)
_cell_angle_gamma                69.240(4)
_cell_formula_units_Z            2
_cell_length_a                   10.4035(16)
_cell_length_b                   10.5900(16)
_cell_length_c                   13.0053(19)
_cell_measurement_reflns_used    4163
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.37
_cell_volume                     1304.9(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9906
_diffrn_measured_fraction_theta_max 0.9906
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20113
_diffrn_reflns_theta_full        27.5822
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.9195.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2153
_exptl_crystal_description       block
_exptl_crystal_F_000             504.4163
_refine_diff_density_max         0.7975
_refine_diff_density_min         -0.6594
_refine_diff_density_rms         0.1590
_refine_ls_d_res_high            0.7675
_refine_ls_d_res_low             9.8717
_refine_ls_goodness_of_fit_ref   1.0676
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0676
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.0644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2931
_reflns_number_total             5999
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob01585j2.cif
_cod_data_source_block           XY20190603111_sx
_cod_depositor_comments
'Adding full bibliography for 7157033--7157035.cif.'
_cod_database_code               7157034
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C25(H25), C27(H27), C29(H29), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C23(H23), C22(H22), C21(H21), C20(H20), C19(H19), N1(H1)
2.b Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C11(H11a,H11b,H11c), C30(H30a,H30b,H30c), C10(H10a,H10b,
 H10c)
;