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_1567899
_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
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04431E
_journal_year                    2022
_chemical_formula_moiety         'C30 H23 N O2'
_chemical_formula_sum            'C30 H23 N O2'
_chemical_formula_weight         429.49
_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             2020-12-30
_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                89.426(3)
_cell_angle_beta                 89.496(3)
_cell_angle_gamma                77.542(3)
_cell_formula_units_Z            2
_cell_length_a                   4.8767(3)
_cell_length_b                   9.4727(7)
_cell_length_c                   24.3972(19)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    300.01
_cell_measurement_theta_max      26.703
_cell_measurement_theta_min      3.322
_cell_volume                     1100.42(14)
_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      300.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0607
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            48049
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         3.322
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0814 before and 0.0602 after correction. The Ratio of minimum to maximum transmission is 0.9396. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0717P)^2^+0.6189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1837
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3247
_reflns_number_total             5071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04431e2.cif
_cod_data_source_block           mo_20201230a_0m_a
_cod_database_code               1567899
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C9-C8A \\sim C9-C8
 with sigma of 0.02
 C8A-C7A \\sim C8-C7
 with sigma of 0.02
 C7A-C6A \\sim C7-C6
 with sigma of 0.02
 C6A-C5A \\sim C6-C5
 with sigma of 0.02
 C5A-C4 \\sim C5-C4
 with sigma of 0.02
3. Restrained planarity
 C4, C5A, C6A, C7A, C8A, C9
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 C9, C8, C7, C6, C5, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C4, C5A, C6A, C7A, C8A, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(H15A)=Sof(H28A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=1-FVAR(1)
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(H28)=Sof(C29)=Sof(H29)=
 Sof(C30)=Sof(H30)=FVAR(1)
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=1-
 FVAR(2)
 Sof(C8)=Sof(H8)=Sof(C7)=Sof(H7)=Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
6.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C5(H5), C11(H11), C11A(H11A), C12(H12), C12A(H12A),
 C13(H13), C13(H13A), C14(H14), C14A(H14A), C15(H15), C15A(H15A), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28),
 C28(H28A), C29(H29), C30(H30), C26A(H26A), C27A(H27A), C29A(H29A), C30A(H30A),
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A)
6.d Fitted hexagon refined as free rotating group:
 C9(C8,C7,C6,C5,C4), C25(C26,C27,C28,C29,C30)
;
_shelx_res_checksum              10706
_shelx_hkl_checksum              64101
_olex2_submission_special_instructions 'No special instructions were received'