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_7160320
_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 rmad
_chemical_formula_moiety         '0.5(C15 H13 N O5), 0.5(C15 H15 N O5)'
_chemical_formula_sum            'C15 H14 N O5'
_chemical_formula_weight         288.27
_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             2020-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-19 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3810(4)
_cell_length_b                   16.4425(7)
_cell_length_c                   20.4203(8)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    240
_cell_measurement_theta_max      74.469
_cell_measurement_theta_min      3.451
_cell_volume                     2814.0(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      240
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'bruker d8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19899
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.757
_diffrn_reflns_theta_min         3.451
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1609 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0948P)^2^+0.0325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5172
_reflns_number_total             5732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01870b2.cif
_cod_data_source_block           cu_22020101_0m
_cod_depositor_comments
'Adding full bibliography for 7160318--7160321.cif.'
_cod_database_code               7160320
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C26(H26), C10(H10), C19(H19), C16(H16), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C00Y(H00A,H00B,H00C), C15(H15A,H15B,H15C), C31(H31A,H31B,
 H31C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'