Silicon Amine Reagents for the Photocatalytic Synthesis of Piperazines from Aldehydes and Ketones.
Hsieh, Sheng-Ying; Bode, Jeffrey W.; Organic letters 18 (2016) 2098–2101; doi:10.1021/acs.orglett.6b00722

data_1555534
_publ_section_title
;
 Silicon Amine Reagents for the Photocatalytic Synthesis of Piperazines
 from Aldehydes and Ketones.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2098
_journal_page_last               2101
_journal_paper_doi               10.1021/acs.orglett.6b00722
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H28 N2 O3'
_chemical_formula_sum            'C20 H28 N2 O3'
_chemical_formula_weight         344.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.609(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7442(9)
_cell_length_b                   6.1717(5)
_cell_length_c                   14.9524(13)
_cell_measurement_reflns_used    966
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.51
_cell_volume                     899.16(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Apex2 Duo (Mo)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5498
_diffrn_reflns_point_group_measured_fraction_full 0.763
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.090
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0408 before and 0.0356 after correction.
The Ratio of minimum to maximum transmission is 0.9209.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 591 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0409P)^2^+0.0486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.362
_reflns_Friedel_fraction_full    0.478
_reflns_Friedel_fraction_max     0.435
_reflns_number_gt                2412
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00722_si_002.cif
_cod_data_source_block           mo_jb141015_1_1_0m
_cod_database_code               1555534
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B),
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              37586
_shelx_hkl_checksum              4412
_olex2_date_sample_data_collection 2015-10-14
_olex2_date_sample_submission    2015-10-14
_olex2_submission_original_sample_id jb141015_1_1
_olex2_submission_special_instructions 'No special instructions were received'