Eco-friendly construction of spiroquinazolin-2-(thi)ones and quinolin-(thio)ureas via Fe(iii)-catalyzed multi-component domino double [4 + 2] annulations
Pan, Zhentao; Shi, Shuaijun; Yang, Xuancheng; Xiao, Xuqiong; Zhang, Wangqin; Wang, Shiliang; Ma, Yongmin; Green Chemistry 23 (2021) 2944–2949; doi:10.1039/D1GC00889G

data_7242532
_publ_section_title
;
 Eco-friendly construction of spiroquinazolin-2-(thi)ones and
 quinolin-(thio)ureas via Fe(iii)-catalyzed multi-component domino double
 [4 + 2] annulations
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2944
_journal_page_last               2949
_journal_paper_doi               10.1039/D1GC00889G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C24 H18 F3 N3 O2'
_chemical_formula_sum            'C24 H18 F3 N3 O2'
_chemical_formula_weight         437.41
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_Hall           '-P 4a'
_space_group_name_H-M_alt        'P 4/n :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-12-23 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.437(3)
_cell_length_b                   24.437(3)
_cell_length_c                   7.3579(8)
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.83
_cell_measurement_theta_min      2.36
_cell_volume                     4393.9(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1101
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32344
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.178
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0772 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0038(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     316
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0753
_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^)+(0.1304P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2099
_reflns_number_total             3874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc00889g2.cif
_cod_data_source_block           mo201104a_sq
_cod_depositor_comments
'Adding full bibliography for 7242532--7242534.cif.'
_cod_original_cell_volume        4394.0(10)
_cod_original_sg_symbol_H-M      'P 4/n'
_cod_database_code               7242532
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C24 \\sim O2-C25
 with sigma of 0.02
 C24-F3 \\sim C25-F6
 with sigma of 0.02
 C24-F1 \\sim C25-F4
 with sigma of 0.02
 C24-F2 \\sim C25-F5
 with sigma of 0.02
 F3-F2 \\sim F6-F5
 with sigma of 0.04
 F1-F2 \\sim F4-F5
 with sigma of 0.04
 F3-F1 \\sim F6-F4
 with sigma of 0.04
 O2-F3 \\sim O2-F6
 with sigma of 0.04
 O2-F1 \\sim O2-F4
 with sigma of 0.04
 O2-F2 \\sim O2-F5
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(C25)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C24)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C19(H19), C20(H20), C22(H22), C23(H23)
5.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              46191
_shelx_fab_checksum              98388
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'