Synthesis of Cyclobutane-Fused Tetracyclic Scaffolds via Visible-Light Photocatalysis for Building Molecular Complexity.
Oderinde, Martins S.; Mao, Edna; Ramirez, Antonio; Pawluczyk, Joseph; Jorge, Christine; Cornelius, Lyndon A. M.; Kempson, James; Vetrichelvan, Muthalagu; Pitchai, Manivel; Gupta, Anuradha; Gupta, Arun Kumar; Meanwell, Nicholas A.; Mathur, Arvind; Dhar, T. G. Murali; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12129

data_4134031
_publ_section_title
;
 Synthesis of Cyclobutane-Fused Tetracyclic Scaffolds via Visible-Light
 Photocatalysis for Building Molecular Complexity.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12129
_journal_year                    2020
_chemical_formula_moiety         'C26 H23 F N2 O'
_chemical_formula_sum            'C26 H23 F N2 O'
_chemical_formula_weight         398.46
_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             2019-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-27 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                96.0480(10)
_cell_angle_beta                 101.3130(10)
_cell_angle_gamma                106.5000(10)
_cell_formula_units_Z            2
_cell_length_a                   7.88970(10)
_cell_length_b                   9.12120(10)
_cell_length_c                   14.9717(2)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      61.03
_cell_measurement_theta_min      3.06
_cell_volume                     998.00(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19676
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        61.192
_diffrn_reflns_theta_max         61.192
_diffrn_reflns_theta_min         3.055
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0635 before and 0.0353 after correction. The Ratio of minimum to maximum transmission is 0.9258. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.2155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2697
_reflns_number_total             2969
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12129_si_002.cif
_cod_data_source_block           13
_cod_database_code               4134031
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C13(H13A,H13B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              28623
_shelx_hkl_checksum              95186
_olex2_submission_special_instructions 'No special instructions were received'