An expeditious FeCl3-catalyzed cascade 1,4-conjugate addition/annulation/1,5-H shift sequence for modular access of all-pyrano-moiety-substituted chromenes
He, Xinwei; Li, Ruxue; Choy, Pui Ying; Duan, Jiahui; Yin, Zhenzhen; Xu, Keke; Tang, Qiang; Zhong, RongLin; Shang, Yongjia; Kwong, Fuk Yee; Chemical Science  (2022) –; doi:10.1039/D2SC04431E

data_1567897
_publ_section_title
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 An expeditious FeCl3-catalyzed cascade 1,4-conjugate
 addition/annulation/1,5-H shift sequence for modular access of
 all-pyrano-moiety-substituted chromenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04431E
_journal_year                    2022
_chemical_formula_moiety         'C30 H21 N O2'
_chemical_formula_sum            'C30 H21 N O2'
_chemical_formula_weight         427.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
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2022-07-07 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.184(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4932(16)
_cell_length_b                   9.8466(12)
_cell_length_c                   17.378(2)
_cell_measurement_reflns_used    5414
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      22.631
_cell_measurement_theta_min      2.981
_cell_volume                     2256.9(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1377
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44868
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.981
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1071 before and 0.0625 after correction. The Ratio of minimum to maximum transmission is 0.9429. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     691
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0932P)^2^+1.4425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.2281
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1859
_reflns_number_total             3960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04431e2.cif
_cod_data_source_block           20200616h
_cod_database_code               1567897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C2-C16 \\sim C2A-C16
 with sigma of 0.02
 C2-C1 \\sim C2A-C1A
 with sigma of 0.02
 O1A-C1A \\sim O1-C1
 with sigma of 0.02
 O1A-C9A \\sim O1-C9
 with sigma of 0.02
 C9-C4 \\sim C9A-C4A
 with sigma of 0.02
 C4-C3 \\sim C4A-C3A
 with sigma of 0.02
 C3A-C2A \\sim C3-C2
 with sigma of 0.02
 N1-C1 \\sim N1A-C1A
 with sigma of 0.02
 C30A-C24A \\sim C26A-C24A
 with sigma of 0.02
 C24-C23 \\sim C24A-C23A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24A \\sim C10 \\sim C11 \\sim C12 \\sim C15 \\sim C25A \\sim C26A \\sim C27A
\\sim C30A \\sim C13 \\sim C28A \\sim C14 \\sim C29A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N1, O1, C1, C9, C2, C4, C8, C10, C3, C16, C5, C7, C11, C15, C23, O2, C17, C6,
 C12, C14, C24, C18, C22, C13, C25, C19, C21, C26, C30, C20, C27, C29, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C3A, O2, C16, C17, C2A, C18, C22, C1A, C19, C21, O1A, N1A, C4A, C23A, C20,
 C9A, C10A, C5A, C24A, C8A, C11A, C15A, C6A, C25A, C7A, C12A, C14A, C26A, C30A,
 C13A, C27A, C29A, C28A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C2A)=Sof(O1A)=Sof(C1A)=Sof(C9A)=Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=
 Sof(C6A)=Sof(H6A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(N1A)=Sof(C10A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(H15A)=Sof(C3A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=
 Sof(H29A)=Sof(C30A)=Sof(H30A)=1-FVAR(1)
 Sof(O1)=Sof(N1)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=Sof(C11)=Sof(H11)=
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=
 Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C8A(H8A), C7A(H7A),
 C6A(H6A), C5A(H5A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
  C23A(H23A), C24A(H24A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A),
 C30A(H30A)
6.b Fitted hexagon refined as free rotating group:
 C9A(C8A,C7A,C6A,C5A,C4A), C10A(C11A,C12A,C13A,C14A,C15A), C25A(C26A,C27A,C28A,
 C29A,C30A)
;
_shelx_res_checksum              58421
_shelx_hkl_checksum              56031
_olex2_submission_special_instructions 'No special instructions were received'