Highly selective synthesis of selenium-containing (<i>E</i>)-<i>N</i>-propenolquinazolinones <i>via</i> FeCl<sub>3</sub>-mediated cascade reaction of propargyl quinazoline-4-yl ethers with diselenides.
Zhang, Xinqin; Yang, Qin; Zeng, Xiaofeng; Fu, Yang; Ding, Qiuping; Peng, Yiyuan; Organic & biomolecular chemistry 22 (2024) 9231–9241; doi:10.1039/d4ob01498g

data_7160188
_publ_section_title
;
 Highly selective synthesis of selenium-containing
 (<i>E</i>)-<i>N</i>-propenolquinazolinones <i>via</i>
 FeCl<sub>3</sub>-mediated cascade reaction of propargyl quinazoline-4-yl
 ethers with diselenides.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9231
_journal_page_last               9241
_journal_paper_doi               10.1039/d4ob01498g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.33(C32 H28 N2 O2 Se)'
_chemical_formula_sum            'C10.67 H9.33 N0.67 O0.67 Se0.33'
_chemical_formula_weight         183.84
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-29 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.5627(11)
_cell_length_b                   14.7048(7)
_cell_length_c                   14.8441(7)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4710
_cell_measurement_theta_min      3.8940
_cell_volume                     2742.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0706
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -10.00  42.00   1.00   19.66    --   16.70  77.00 -90.00   52
  2  \w    -15.00  55.00   1.00   19.66    --   16.70 -99.00  90.00   70
  3  \w     -3.00  86.00   1.00   19.66    --   16.70  37.00 150.00   89
  4  \w    -45.00  16.00   1.00   19.66    --  -15.76  19.00-120.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0337244000
_diffrn_orient_matrix_UB_12      0.0306929000
_diffrn_orient_matrix_UB_13      0.0232195000
_diffrn_orient_matrix_UB_21      -0.0410264000
_diffrn_orient_matrix_UB_22      -0.0331562000
_diffrn_orient_matrix_UB_23      0.0002743000
_diffrn_orient_matrix_UB_31      0.0191048000
_diffrn_orient_matrix_UB_32      -0.0169090000
_diffrn_orient_matrix_UB_33      0.0417749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16662
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.521
_diffrn_reflns_theta_min         3.476
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             1136
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.006(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                4030
_reflns_number_total             6380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01498g2.cif
_cod_data_source_block           zxq-1-3_auto
_cod_depositor_comments          'Adding full bibliography for 7160188.cif.'
_cod_database_code               7160188
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.006(12)
 -0.006(12)
2. 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, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C00R(H00R)
3.b Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00C)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J),
 C00K(H00K), C00M(H00M), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
3.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              2789
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.259
_oxdiff_exptl_absorpt_empirical_full_min 0.597