Spirocyclic iridoid alkaloids from <i>Plumeria rubra</i>.
Gao, Xin-Hua; Zhou, Bin; Zimbres, Flavia M.; Zhang, Zai-Yong; Cassera, Maria B.; Zhao, Jin-Xin; Yue, Jian-Min; Organic & biomolecular chemistry 23 (2025) 960–966; doi:10.1039/d4ob01870b

data_7160318
_publ_section_title
;
 Spirocyclic iridoid alkaloids from <i>Plumeria rubra</i>.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              960
_journal_page_last               966
_journal_paper_doi               10.1039/d4ob01870b
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28
_chemical_name_systematic        PR-9
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-08-19 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.6270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.14340(10)
_cell_length_b                   10.1986(2)
_cell_length_c                   11.1002(2)
_cell_measurement_reflns_used    7436
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      140.316
_cell_measurement_theta_min      8.670
_cell_volume                     693.21(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8372
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.152
_diffrn_reflns_theta_min         7.983
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
; 
 Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_coef       0.074(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0357P)^2^+0.0691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0745
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                2493
_reflns_number_total             2531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01870b2.cif
_cod_data_source_block           cu_d8v18303_0m
_cod_depositor_comments
'Adding full bibliography for 7160318--7160321.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160318
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.902
_shelxl_version_number           2013-4
_shelx_res_checksum              19502