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_7159319
_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 H21 Cl N2 O'
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_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   mixed
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_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2485(2)
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_cell_measurement_reflns_used    16395
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.73
_cell_volume                     1619.70(8)
_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)'
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_computing_publication_material  'Bruker APEX4'
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_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.229
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.8231
_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            light-yellow
_exptl_crystal_density_diffrn    1.348
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_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.034
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_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0245P)^2^+0.9832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3317
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00439b2.cif
_cod_data_source_block           ic21750
_cod_depositor_comments
'Adding full bibliography for 7159317--7159320.cif.'
_cod_database_code               7159319
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.880
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              36683