Streamlined Synthesis of C(sp<sup>3</sup>)-Rich N-Heterospirocycles Enabled by Visible-Light-Mediated Photocatalysis.
Flodén, Nils J; Trowbridge, Aaron; Willcox, Darren; Walton, Scarlett M.; Kim, Yongjoon; Gaunt, Matthew J.; Journal of the American Chemical Society 141 (2019) 8426–8430; doi:10.1021/jacs.9b03372

data_4127277
_publ_section_title
;
 Streamlined Synthesis of C(sp<sup>3</sup>)-Rich N-Heterospirocycles
 Enabled by Visible-Light-Mediated Photocatalysis.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8426
_journal_page_last               8430
_journal_paper_doi               10.1021/jacs.9b03372
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 F2 N O'
_chemical_formula_sum            'C15 H17 F2 N O'
_chemical_formula_weight         265.29
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                76.493(2)
_cell_angle_beta                 89.622(3)
_cell_angle_gamma                78.571(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7759(2)
_cell_length_b                   10.3846(4)
_cell_length_c                   11.5759(4)
_cell_measurement_reflns_used    3835
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.33
_cell_measurement_theta_min      3.93
_cell_volume                     661.16(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7696
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.931
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_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     172
_refine_ls_number_reflns         2338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0405P)^2^+0.2573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1726
_reflns_number_total             2338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b03372_si_002.cif
_cod_data_source_block           MG_B1_0053
_cod_depositor_comments
'Adding full bibliography for 4127277--4127278.cif.'
_cod_database_code               4127277
_cambridge_user_name             'Nils Floden'
_cambridge_user_crsid            njf41
_cambridge_supervisor_name       'Matthew Gaunt'
_cambridge_supervisor_crsid      mjg32
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             NJF-difluorocyclopropane
_cambridge_data_id               MG_B1_0053
_ccdc_publ_extra_info
;
_cambridge_sample_id NJF-difluorocyclopropane
_cambridge_data_id MG_B1_0053
;
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.958