Direct photochemical intramolecular [4 + 2] cycloadditions of dehydrosecodine-type substrates for the synthesis of the <i>iboga</i>-type scaffold and divergent [2 + 2] cycloadditions employing micro-flow system.
Tay, Gavin; Nishimura, Soushi; Oguri, Hiroki; Chemical science 15 (2024) 15599–15609; doi:10.1039/d4sc02597k

data_1572693
_publ_section_title
;
 Direct photochemical intramolecular [4 + 2] cycloadditions of
 dehydrosecodine-type substrates for the synthesis of the
 <i>iboga</i>-type scaffold and divergent [2 + 2] cycloadditions employing
 micro-flow system.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              15599
_journal_page_last               15609
_journal_paper_doi               10.1039/d4sc02597k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C24 H28 N2 O4'
_chemical_formula_sum            'C24 H28 N2 O4'
_chemical_formula_weight         408.48
_chemical_name_systematic        'Bowl-type scaffold'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.388(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4706(18)
_cell_length_b                   11.081(2)
_cell_length_c                   18.106(3)
_cell_measurement_reflns_used    19879
_cell_measurement_temperature    109.0
_cell_measurement_theta_max      97.361
_cell_measurement_theta_min      0.71081
_cell_volume                     2083.3(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      109.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1843
_diffrn_reflns_av_unetI/netI     0.1745
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         1.961
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0781 after correction.
The Ratio of minimum to maximum transmission is 0.8429.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_preparation       'vapor diffusion method DCM/hex'
_exptl_crystal_recrystallization_method 'vapor diffusion method DCM/hex'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.1976
_refine_ls_R_factor_gt           0.0772
_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^)+(0.1071P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.2437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1557
_reflns_number_total             3845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02597k2.cif
_cod_data_source_block           Bowl-type_scaffold
_cod_depositor_comments
'Adding full bibliography for 1572691--1572693.cif.'
_cod_database_code               1572693
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
;
_shelx_res_checksum              82325
_olex2_exptl_crystal_mounting_method 'Manual mounting using Rigaku loop'
_olex2_submission_original_sample_id 'Bowl-type scaffold'
_olex2_submission_special_instructions 'No special instructions were received'