Visible-light promoted radical cascade cyclization of 3-allyl-2-arylquinazolinones for the synthesis of phosphorylated dihydroisoquinolino[1,2-<i>b</i>]quinazolinones.
Huang, Jun; Ban, Caijin; Qin, Jiangping; Xu, Jiali; Gu, Yunqiong; Wei, Liang; Yuan, Jing-Mei; Huang, Guobao; Chemical communications (Cambridge, England) 60 (2024) 8119–8122; doi:10.1039/d4cc02915a

data_7133303
_publ_section_title
;
 Visible-light promoted radical cascade cyclization of
 3-allyl-2-arylquinazolinones for the synthesis of phosphorylated
 dihydroisoquinolino[1,2-<i>b</i>]quinazolinones.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8119
_journal_page_last               8122
_journal_paper_doi               10.1039/d4cc02915a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H23 N2 O2 P'
_chemical_formula_sum            'C29 H23 N2 O2 P'
_chemical_formula_weight         462.46
_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             2024-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-16 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8254(6)
_cell_length_b                   13.4214(5)
_cell_length_c                   11.2282(5)
_cell_measurement_reflns_used    6356
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.37
_cell_volume                     2230.86(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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_temperature      150.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.0602
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            42560
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_min         2.367
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.4022.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0687
_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^)+(0.0393P)^2^+1.9835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3587
_reflns_number_total             4544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02915a2.cif
_cod_data_source_block           mo_0424_1_0ma
_cod_depositor_comments          'Adding full bibliography for 7133303.cif.'
_cod_database_code               7133303
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C16, C13, C12, C11, C15, C14
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C18, C8, C7, C3, C4, C5
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N3, N005, N4, N004
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(N4)=
 Sof(C9)=Sof(C7)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C18)=Sof(H18)=
 Sof(C8)=Sof(H8)=Sof(C10)=Sof(N3)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(C15)=Sof(C16)=
 Sof(H16)=Sof(C14)=Sof(H14)=Sof(C13)=Sof(H13)=Sof(O1)=1-FVAR(1)
 Sof(O003)=Sof(N004)=Sof(N005)=Sof(C00A)=Sof(H00A)=Sof(C00B)=Sof(C00C)=
 Sof(C00F)=Sof(C00G)=Sof(C00H)=Sof(H00H)=Sof(C00I)=Sof(C00J)=Sof(H00B)=
 Sof(H00C)=Sof(C00M)=Sof(H00F)=Sof(H00G)=Sof(C00N)=Sof(H00N)=Sof(C00P)=
 Sof(H00P)=Sof(C00Q)=Sof(H00Q)=Sof(C00U)=Sof(H00U)=Sof(C00V)=Sof(H00V)=
 Sof(C00W)=Sof(H00W)=Sof(C00X)=Sof(C00Y)=Sof(H00Y)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C00W(H00W), C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C00J(H00B,H00C), C00M(H00F,H00G), C1(H1A,H1B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00H(H00H),
 C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00Y(H00Y), C4(H4),
  C5(H5), C18(H18), C8(H8), C12(H12), C16(H16), C14(H14), C13(H13)
4.d Fitted hexagon refined as free rotating group:
 C7(C3,C4,C5,C18,C8), C12(C11,C15,C16,C14,C13)
;
_shelx_res_checksum              86831
_shelx_hkl_checksum              88861
_olex2_submission_special_instructions 'No special instructions were received'