From citronellal to iridoids: asymmetric synthesis of iridoids and their analogues <i>via</i> organocatalytic intramolecular Michael reactions.
Tammisetti, Raviramanujayya; Chaudhari, Prakash D.; Hong, Bor-Cherng; Chien, Su-Ying; Organic & biomolecular chemistry 21 (2023) 4200–4205; doi:10.1039/d3ob00439b

data_7159317
_publ_section_title
;
 From citronellal to iridoids: asymmetric synthesis of iridoids and their
 analogues <i>via</i> organocatalytic intramolecular Michael reactions.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4200
_journal_page_last               4205
_journal_paper_doi               10.1039/d3ob00439b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C16 H20 N4 O6'
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_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                74.980(12)
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_cell_measurement_temperature    200(2)
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_cell_volume                     872.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
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_diffrn_reflns_av_unetI/netI     0.0977
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_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_theta_max         67.980
_diffrn_reflns_theta_min         3.933
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_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
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_exptl_crystal_size_min          0.159
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_refine_diff_density_min         -0.447
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_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.379
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.1206
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2821
_refine_ls_wR_factor_ref         0.3346
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                2944
_reflns_number_total             5724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00439b2.cif
_cod_data_source_block           ic21707
_cod_depositor_comments
;
Adding full bibliography for 7159317--7159320.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H40 N8 O12'
_cod_original_formula_weight         728.72
_cod_original_formula_units_Z            1
_cod_database_code               7159317
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.611
_shelx_estimated_absorpt_t_max   0.869
_shelx_res_checksum              30917