Metal-free direct alkylation of unfunctionalized allylic/benzylic sp3 CH bonds via photoredox induced radical cation deprotonation
Zhou, Rong; Liu, Haiwang; Tao, Hairong; Yu, Xingjian; Wu, Jie; Chem. Sci.  (2017) –; doi:10.1039/C7SC00953D

data_1545899
_publ_section_title
;
 Metal-free direct alkylation of unfunctionalized allylic/benzylic sp3
 C&#xF02D;H bonds via photoredox induced radical cation deprotonation
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC00953D
_journal_year                    2017
_chemical_formula_sum            'C20 H24 N2'
_chemical_formula_weight         292.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-26 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.818(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6451(18)
_cell_length_b                   5.8536(6)
_cell_length_c                   19.416(2)
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.90
_cell_measurement_theta_min      2.96
_cell_volume                     1730.7(3)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1171
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14377
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.678
_diffrn_reflns_theta_max         66.678
_diffrn_reflns_theta_min         2.963
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0794
_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^)+(0.1405P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1837
_reflns_number_total             3030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00953d2.cif
_cod_data_source_block           G402
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1730.6(3)
_cod_database_code               1545899
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.756
_shelx_estimated_absorpt_t_max   0.979
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelx_res_checksum              85054
_shelx_hkl_checksum              76816