Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation.
Faltracco, Matteo; Cotogno, Silvia; Vande Velde, Christophe M. L.; Ruijter, Eelco; The Journal of organic chemistry 84 (2019) 12058–12070; doi:10.1021/acs.joc.9b01994

data_4034440
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular
 Tsuji-Trost Allylation.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12058
_journal_page_last               12070
_journal_paper_doi               10.1021/acs.joc.9b01994
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration R
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37
_chemical_name_systematic
(R)-4-benzyl-3-vinyl-1,4-diazaspiro[5.5]undecane-2,5-dione
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 101.426(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3081(3)
_cell_length_b                   10.6674(3)
_cell_length_c                   13.9179(4)
_cell_measurement_reflns_used    4341
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.6890
_cell_measurement_theta_min      3.2190
_cell_volume                     1645.62(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13436
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.203
_diffrn_reflns_theta_min         3.240
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0523P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.877
_reflns_Friedel_fraction_max     0.817
_reflns_number_gt                4982
_reflns_number_total             6159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01994_si_002.cif
_cod_data_source_block           mfo870c
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034440
_shelx_shelxl_version_number     2016/4
_oxdiff_exptl_absorpt_empirical_full_min 0.492
_oxdiff_exptl_absorpt_empirical_full_max 23.358
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              54082
_shelx_hkl_checksum              45752