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_7242534
_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         'C23 H14 N3 O S'
_chemical_formula_sum            'C23 H14 N3 O S'
_chemical_formula_weight         380.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-02-05 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                98.57(3)
_cell_angle_beta                 95.81(3)
_cell_angle_gamma                92.80(3)
_cell_formula_units_Z            8
_cell_length_a                   13.632(18)
_cell_length_b                   13.694(18)
_cell_length_c                   22.48(3)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.19
_cell_volume                     4120(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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.832
_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  0.0901
_diffrn_reflns_av_unetI/netI     0.1918
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            39197
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         1.640
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0597 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.8966.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     985
_refine_ls_number_reflns         21066
_refine_ls_number_restraints     936
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.2273
_refine_ls_R_factor_gt           0.0746
_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^)+(0.0818P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.2275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6894
_reflns_number_total             21066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc00889g2.cif
_cod_data_source_block           mo210122a_sq
_cod_depositor_comments
'Adding full bibliography for 7242532--7242534.cif.'
_cod_database_code               7242534
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. 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
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27),
  C28(H28), C29(H29), C33(H33), C34(H34), C35(H35), C36(H36), C39(H39),
 C40(H40), C42(H42), C43(H43), C41(H41), C039(H039), C47(H47), C48(H48),
 C49(H49), C50(H50), C54(H54), C55(H55), C56(H56), C57(H57), C60(H60), C61(H61),
  C64(H64), C65(H65), C66(H66), C67(H67), C033(H033), C70(H70), C71(H71),
 C72(H72), C73(H73), C77(H77), C78(H78), C79(H79), C82(H82), C83(H83), C87(H87),
  C88(H88), C85(H85), C86(H86)
3.b Fitted hexagon refined as free rotating group:
 C42(C43,C44,C02V,C41,C039), C87(C88,C89,C84,C85,C86)
;
_shelx_res_checksum              63288
_shelx_fab_checksum              6693
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'