Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD Ring Cores of Camptothecins.
Yuan, Yao; Dong, Wuheng; Gao, Xiaoshuang; Gao, Huang; Xie, Xiaomin; Zhang, Zhaoguo; The Journal of organic chemistry 83 (2018) 2840–2846; doi:10.1021/acs.joc.7b03283

data_4034952
_publ_section_title
;
 Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD
 Ring Cores of Camptothecins.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2840
_journal_page_last               2846
_journal_paper_doi               10.1021/acs.joc.7b03283
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H9 F N2 O'
_chemical_formula_sum            'C15 H9 F N2 O'
_chemical_formula_weight         252.24
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                100.1500(10)
_cell_angle_beta                 90.8700(10)
_cell_angle_gamma                97.2970(10)
_cell_formula_units_Z            2
_cell_length_a                   4.81580(10)
_cell_length_b                   8.0560(2)
_cell_length_c                   14.3600(4)
_cell_measurement_reflns_used    6875
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      3.13
_cell_volume                     543.55(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8771
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         3.129
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0571P)^2^+0.1137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1768
_reflns_number_total             1911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03283_si_003.cif
_cod_data_source_block           a
_cod_database_code               4034952
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              89127
_shelx_hkl_checksum              17251