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_7133231
_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 H17 Cl O5'
_chemical_formula_sum            'C24 H17 Cl O5'
_chemical_formula_weight         420.852
_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             2024-02-13
_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                101.327(5)
_cell_angle_beta                 97.246(6)
_cell_angle_gamma                92.314(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3859(13)
_cell_length_b                   10.8372(18)
_cell_length_c                   12.379(2)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.79
_cell_volume                     961.6(3)
_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      299.00
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9983
_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  0.0367
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35340
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9983
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.92
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1378 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.9195.
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    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             436.580
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.013
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.2472
_refine_diff_density_min         -0.2504
_refine_diff_density_rms         0.0498
_refine_ls_d_res_high            0.7493
_refine_ls_d_res_low             10.6023
_refine_ls_goodness_of_fit_ref   1.0964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0964
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.0027
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.2123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3776
_reflns_number_total             4772
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc01953a2.cif
_cod_data_source_block           D215_02_0m_a
_cod_depositor_comments
'Adding full bibliography for 7133230--7133231.cif.'
_cod_database_code               7133231
_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:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C22(H22), C21(H21), C20(H20), C19(H19), C18(H18), C5(H5), C4(H4),
 C3(H3), C2(H2)
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'