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_7132830
_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         'C28 H30 Br N3 O5'
_chemical_formula_sum            'C28.01 H30.01 Br N3 O5'
_chemical_formula_weight         568.65
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-08-15
_audit_creation_method
;FinalCif V117 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-11-06 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                115.124(2)
_cell_angle_beta                 105.133(3)
_cell_angle_gamma                100.196(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0881(8)
_cell_length_b                   11.9277(9)
_cell_length_c                   12.1514(9)
_cell_measurement_reflns_used    5919
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      24.80
_cell_measurement_theta_min      2.24
_cell_volume                     1326.22(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.16/2021-10-22 && APEX4 2021.10-0'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37795
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.240
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5574
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.3504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3509
_reflns_number_total             4666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06327e2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 7132829--7132830.cif.'
_cod_original_cell_volume        1326.22(17)
_cod_database_code               7132830
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C4(H4), C19(H19), C10(H10), C5(H5), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C7(H7A,H7B,
 H7C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              24319
_shelx_hkl_checksum              45099