Chemodivergent mechanosynthesis of cyclopentenyl and pyrrolinyl spirobarbiturates from unsaturated barbiturates and enamino esters.
Li, Ming-Jun; Lu, Ming-Ming; Xu, Peng; Chen, Si-Qi; Wu, Luan-Ting; Zhang, Ze; Xu, Hui; Chemical communications (Cambridge, England) 60 (2024) 3958–3961; doi:10.1039/d3cc06327e

data_7132829
_publ_section_title
;
 Chemodivergent mechanosynthesis of cyclopentenyl and pyrrolinyl
 spirobarbiturates from unsaturated barbiturates and enamino esters.
;
_journal_issue                   29
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3958
_journal_page_last               3961
_journal_paper_doi               10.1039/d3cc06327e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C26 H26 Cl N3 O5'
_chemical_formula_sum            'C26 H26 Cl N3 O5'
_chemical_formula_weight         495.95
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-06 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.073(2)
_cell_angle_beta                 98.225(2)
_cell_angle_gamma                110.945(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2719(11)
_cell_length_b                   10.9748(14)
_cell_length_c                   14.3779(18)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.37
_cell_volume                     1203.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_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_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6128
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.543
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0659P)^2^+0.2610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3112
_reflns_number_total             4196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06327e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7132829--7132830.cif.'
_cod_database_code               7132829
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C7(H7A,H7B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C20(H20), C5(H5), C1(H1A), C19(H19), C18(H18), C2(H2),
 C4(H4), C3(H3)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              1921
_shelx_hkl_checksum              9710
_olex2_submission_special_instructions 'No special instructions were received'