Synthesis of arene-functionalized fused heterocyclic scaffolds <i>via</i> a regioselective cascade 1,4-conjugate addition/5-<i>exo-dig</i> annulation strategy.
He, Xinwei; Wang, Demao; Liu, Yanan; Wu, Mengdi; Kong, Yangzilin; Tang, Qiang; Wang, Yiping; Fan, Chenli; Shang, Yongjia; Organic & biomolecular chemistry 21 (2023) 9159–9172; doi:10.1039/d3ob01572f

data_7159679
_publ_section_title
;
 Synthesis of arene-functionalized fused heterocyclic scaffolds <i>via</i>
 a regioselective cascade 1,4-conjugate addition/5-<i>exo-dig</i>
 annulation strategy.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9159
_journal_page_last               9172
_journal_paper_doi               10.1039/d3ob01572f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H17 N O3, 0.25[C4H8O2]'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   23.118(12)
_cell_length_b                   23.118(12)
_cell_length_c                   14.243(9)
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      19.468
_cell_measurement_theta_min      2.432
_cell_volume                     7612(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractrometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1790
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.750
_diffrn_reflns_theta_max         24.750
_diffrn_reflns_theta_min         1.679
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.7993.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     320
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.2022
_refine_ls_R_factor_gt           0.0862
_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^)+(0.1055P)^2^+9.2012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2671
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1300
_reflns_number_total             3248
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01572f2.cif
_cod_data_source_block           230523c_sq
_cod_depositor_comments
'Adding full bibliography for 7159677--7159679.cif.'
_cod_original_cell_volume        7612(9)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7159679
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8-C15A \\sim C8-C15
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C15 \\sim C17 \\sim C19 \\sim C18 \\sim C20 \\sim C16 \\sim C15A \\sim C17A
\\sim C19A \\sim C18A \\sim C21A \\sim C20A \\sim C16A \\sim C21: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C15, C8, C17, C19, C18, C21, C20, C16, C15A, C17A, C19A, C18A, C21A, C20A, C16A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7)
6.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C3(H3), C11(H11), C15A(H15A), C17A(H17A), C18A(H18A),
 C19A(H19A), C20A(H20A), C21A(H21A)
6.c Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C21), C16A(C17A,C18A,C19A,C20A,C21A)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.e Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_shelx_res_checksum              88277
_shelx_fab_checksum              49689
_platon_squeeze_special_details
;
A solvent mask was calculated and 220 electrons were 
found in a volume of 1020\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.25[C4H8O2] per Asymmetric Unit 
which account for 192 electrons 
per unit cell.
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'