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_7159318
_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            'C19 H23 N2 O1.5'
_chemical_formula_weight         303.39
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                73.2229(17)
_cell_angle_beta                 86.5859(18)
_cell_angle_gamma                65.2493(15)
_cell_formula_units_Z            2
_cell_length_a                   8.6926(4)
_cell_length_b                   10.2171(5)
_cell_length_c                   10.4436(5)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.59
_cell_volume                     804.46(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            25318
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.294
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.8889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       needle
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 3255 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.5(5)
_refine_ls_extinction_coef       0.047(6)
_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   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         9341
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0233P)^2^+0.2650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                7817
_reflns_number_total             9341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00439b2.cif
_cod_data_source_block           ic21774
_cod_depositor_comments
;
Adding full bibliography for 7159317--7159320.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H46 N4 O3'
_cod_original_formula_weight         606.79
_cod_original_formula_units_Z            1
_cod_database_code               7159318
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              91452