Catalyst-free racemic and H2O/CPA-catalyzed asymmetric regio-reversed domino processes of triketone enones with azlactones
Fu, Yun-Dong; Gao, Xiang; Jia, Shi-Kun; Xiao, Xiao; Wang, Min-Can; Huang, Lihua; Mei, Guang-Jian; Green Chemistry 25 (2023) 5692–5697; doi:10.1039/D3GC01445B

data_7246940
_publ_section_title
;
 Catalyst-free racemic and H2O/CPA-catalyzed asymmetric regio-reversed
 domino processes of triketone enones with azlactones
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5692
_journal_page_last               5697
_journal_paper_doi               10.1039/D3GC01445B
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H25 N O8'
_chemical_formula_sum            'C26 H25 N O8'
_chemical_formula_weight         479.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-19 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6044(5)
_cell_length_b                   9.6671(6)
_cell_length_c                   31.908(2)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      58.66
_cell_measurement_theta_min      4.16
_cell_volume                     2345.6(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            39600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.453
_diffrn_reflns_theta_min         4.157
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1375 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.8949.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0354P)^2^+1.1374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4529
_reflns_number_total             5280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01445b2.cif
_cod_data_source_block           230318lu_lgpz144707_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7246940.cif.
;
_cod_database_code               7246940
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.933
_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. Restrained distances
 O8-C25 \\sim O8-C25A
 with sigma of 0.02
 C18A-C17 \\sim C18-C17
 with sigma of 0.02
 O1A-C1A \\sim O1-C1
 with sigma of 0.02
 C26A-C25A \\sim C26-C25
 with sigma of 0.02
 O1-C2 \\sim O1A-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25 \\sim C26A \\sim C26 \\sim C25A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
O1A \\sim O1 \\sim C1 \\sim C1A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(O1A)=1-FVAR(1)
 Sof(O1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
 Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C25A)=Sof(H25C)=Sof(H25D)=1-FVAR(2)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26D)=Sof(H26E)=Sof(H26F)=FVAR(2)
 Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=
 Sof(H23A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=1-FVAR(3)
 Sof(C18)=Sof(C23)=Sof(H23)=Sof(C22)=Sof(H22)=Sof(C21)=Sof(H21)=Sof(C20)=
 Sof(H20)=Sof(C19)=Sof(H19)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C25A(H25C,H25D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C4(H4), C3(H3), C7(H7), C6(H6), C20A(H20A), C21A(H21A),
 C22A(H22A), C23A(H23A), C19A(H19A), C23(H23), C22(H22), C21(H21), C20(H20),
 C19(H19)
5.c Fitted hexagon refined as free rotating group:
 C20A(C21A,C22A,C23A,C18A,C19A), C18(C23,C22,C21,C20,C19)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C26A(H26A,H26B,
 H26C), C1A(H1AA,H1AB,H1AC), C26(H26D,H26E,H26F)
;
_shelx_res_checksum              72103
_shelx_hkl_checksum              1547
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU