An organocatalytic domino annulation approach <i>via</i> C(sp<sup>2</sup>)-OMe cleavage to unlock the synthesis of pyranochromenones enabled by HFIP.
Singh, Sanjay; Sharma, Pragya; Dutta, Sayantan; Vishwakarma, Rahul; Hazra, Chinmoy K.; Chemical communications (Cambridge, England) 60 (2024) 7200–7203; doi:10.1039/d4cc01953a

data_7133230
_publ_section_title
;
 An organocatalytic domino annulation approach <i>via</i>
 C(sp<sup>2</sup>)-OMe cleavage to unlock the synthesis of
 pyranochromenones enabled by HFIP.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7200
_journal_page_last               7203
_journal_paper_doi               10.1039/d4cc01953a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H18 O5'
_chemical_formula_sum            'C24 H18 O5'
_chemical_formula_weight         386.407
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-02-22 deposited with the CCDC.	2024-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                63.736(10)
_cell_angle_beta                 87.201(10)
_cell_angle_gamma                78.910(9)
_cell_formula_units_Z            2
_cell_length_a                   8.3038(18)
_cell_length_b                   11.289(3)
_cell_length_c                   11.546(3)
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.50
_cell_volume                     951.7(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9932
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.9968
_diffrn_reflns_Laue_measured_fraction_max 0.9932
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27980
_diffrn_reflns_point_group_measured_fraction_full 0.9968
_diffrn_reflns_point_group_measured_fraction_max 0.9932
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.12
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.7483.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             404.281
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.013
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.3995
_refine_diff_density_min         -0.2914
_refine_diff_density_rms         0.0722
_refine_ls_d_res_high            0.7495
_refine_ls_d_res_low             9.5900
_refine_ls_goodness_of_fit_ref   1.0375
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0375
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.0783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2600
_reflns_number_total             4688
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc01953a2.cif
_cod_data_source_block           ss02_0m_a
_cod_depositor_comments
'Adding full bibliography for 7133230--7133231.cif.'
_cod_original_cell_volume        951.6(4)
_cod_database_code               7133230
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'