Selective Piperidine Synthesis Exploiting Iodine-Catalyzed Csp3–H Amination under Visible Light
Zhang, Hongwei; Muñiz, Kilian; ACS Catalysis 7 (2017) 4122–; doi:10.1021/acscatal.7b00928

data_4514142
_publ_section_title
;
 Selective Piperidine Synthesis Exploiting Iodine-Catalyzed Csp3--H
 Amination under Visible Light
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              4122
_journal_paper_doi               10.1021/acscatal.7b00928
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C21 H27 N O2 S'
_chemical_formula_weight         357.50
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90
_cell_angle_beta                 114.637(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6983(3)
_cell_length_b                   13.0767(3)
_cell_length_c                   13.6557(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1898.82(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
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_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.012
_diffrn_reflns_theta_min         2.997
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             768
_refine_diff_density_max         0.671
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_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0369
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+1.1133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4172
_reflns_number_total             4596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00928_si_005.cif
_cod_data_source_block           ZHW7me
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1898.81(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_sum        'C10.50 H13.50 N0.50 O S0.50'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     178.75
_cod_database_code               4514142
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              79739
_shelx_hkl_checksum              29928