Diastereoselective Synthesis of Functionalized Diketopiperazines through Post-transformational Reactions.
Balalaie, Saeed; Ramezani Kejani, Reihaneh; Ghabraie, Elmira; Darvish, Fatemeh; Rominger, Frank; Hamdan, Fatima; Bijanzadeh, Hamid Reza; The Journal of organic chemistry 82 (2017) 12141–12152; doi:10.1021/acs.joc.7b01855

data_4033100
_publ_section_title
;
 Diastereoselective Synthesis of Functionalized Diketopiperazines through
 Post-transformational Reactions.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12141
_journal_page_last               12152
_journal_paper_doi               10.1021/acs.joc.7b01855
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C23 H23 Cl N2 O2'
_chemical_formula_weight         394.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 105.812(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8038(14)
_cell_length_b                   17.766(3)
_cell_length_c                   13.229(2)
_cell_measurement_reflns_used    1911
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      19.33
_cell_measurement_theta_min      2.29
_cell_volume                     1990.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
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_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13334
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        21.892
_diffrn_reflns_theta_max         21.892
_diffrn_reflns_theta_min         1.968
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.8777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     225
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0293P)^2^+2.6479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1838
_reflns_number_total             2397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01855_si_002.cif
_cod_data_source_block           sba132
_cod_depositor_comments
'Adding full bibliography for 4033100--4033101.cif.'
_cod_database_code               4033100
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              20982
_shelx_hkl_checksum              26173