Base-promoted cascade vinylogous Michael/Michael addition of alkylidene succinimides for the construction of penta-substituted cyclopentanes.
Liang, Peiyao; Chen, Siyi; Liu, Xin; Teng, Shenghan; Wang, Shoulei; Organic & biomolecular chemistry 22 (2024) 8832–8837; doi:10.1039/d4ob01455c

data_7160176
_publ_section_title
;
 Base-promoted cascade vinylogous Michael/Michael addition of alkylidene
 succinimides for the construction of penta-substituted cyclopentanes.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8832
_journal_page_last               8837
_journal_paper_doi               10.1039/d4ob01455c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C36 H27 Cl N4 O4, 0.524[CH2Cl2]'
_chemical_formula_sum            'C36.53 H28.05 Cl2.05 N4 O4'
_chemical_formula_weight         659.65
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-05 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                85.940(2)
_cell_angle_beta                 81.147(2)
_cell_angle_gamma                76.613(2)
_cell_formula_units_Z            4
_cell_length_a                   11.6545(7)
_cell_length_b                   15.2783(9)
_cell_length_c                   18.4930(10)
_cell_measurement_reflns_used    9347
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      2.51
_cell_volume                     3163.1(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0839
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            87224
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.508
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1057 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9099.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.360
_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     803
_refine_ls_number_reflns         14465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0690P)^2^+0.3347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9241
_reflns_number_total             14465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01455c2.cif
_cod_data_source_block           2023111501_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160176.cif.'
_cod_database_code               7160176
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C46(H46), C53(H53), C14(H14), C54(H54), C21(H21), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C52(H52), C48(H48), C40(H40), C34(H34), C35(H35), C32(H32), C23(H23),
 C50(H50), C51(H51), C49(H49), C25(H25), C37(H37), C39(H39), C24(H24), C62(H62),
  C58(H58), C66(H66), C70(H70), C20(H20), C67(H67), C69(H69), C16(H16),
 C68(H68), C27(H27), C60(H60), C61(H61), C26(H26), C59(H59), C1(H1), C5(H5),
 C4(H4), C3(H3), C2(H2), C19(H19), C17(H17), C18(H18)
2.c Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C30(H30A,H30B,H30C), C72(H72A,H72B,H72C), C45(H45A,H45B,
 H45C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 88 electrons were 
found in a volume of 264\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1.048[CH2Cl2] per formula unit 
which account for 88 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              37344
_shelx_fab_checksum              91685
_olex2_submission_special_instructions 'No special instructions were received'