An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
Li, Jie; Huang, Jiu Hong; Wang, Jing Ya; Xu, Zhi Gang; Chen, Zhong Zhu; Lei, Jie; RSC Advances 12 (2022) 33175–33179; doi:10.1039/D2RA04958A

data_7245872
_publ_section_title
;
 An intramolecular hydrogen bond-promoted &#x201C;green&#x201D; Ugi
 cascade reaction for the synthesis of 2,5-diketopiperazines with
 anticancer activity
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              33175
_journal_page_last               33179
_journal_paper_doi               10.1039/D2RA04958A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C33 H29 N3 O3'
_chemical_formula_weight         515.59
_chemical_name_systematic
'1-(2-(1<i>H</i>-indol-3-yl)ethyl)-4-benzyl-3-hydroxy-3,6- diphenylpiperazine-2,5-dione'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc25fkck
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-10 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                92.354(2)
_cell_angle_beta                 103.338(2)
_cell_angle_gamma                91.502(2)
_cell_formula_units_Z            2
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_cell_length_b                   12.8851(13)
_cell_length_c                   15.0472(15)
_cell_measurement_reflns_used    4097
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.79
_cell_volume                     1341.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
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_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6862
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.137
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       BLOCK
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_exptl_crystal_size_max          0.300
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_exptl_crystal_size_min          0.270
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_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0646P)^2^+0.2652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3871
_reflns_number_total             4688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra04958a2.cif
_cod_data_source_block           1
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_shelx_shelxl_version_number     2014/7
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_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              61952