#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:00:49 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299087 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160320.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160320
loop_
_publ_author_name
'Gao, Xin-Hua'
'Zhou, Bin'
'Zimbres, Flavia M.'
'Zhang, Zai-Yong'
'Cassera, Maria B.'
'Zhao, Jin-Xin'
'Yue, Jian-Min'
_publ_section_title
;
 Spirocyclic iridoid alkaloids from Plumeria rubra.
;
_journal_issue                   4
_journal_name_full               'Organic & 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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0948P)²+0.0325P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O10 O 1.1623(3) 0.66566(11) 0.50584(10) 0.0511(4) Uani 1 1 d . . . . .
O3 O 1.1105(3) 0.44832(14) 0.75048(9) 0.0544(5) Uani 1 1 d . . . . .
O1 O 0.7625(3) 0.54311(14) 0.91339(11) 0.0570(5) Uani 1 1 d . . . . .
H1 H 0.702078 0.504194 0.906029 0.086 Uiso 1 1 calc GR . . . .
O7 O 0.8029(3) 0.42074(17) 0.66046(10) 0.0650(6) Uani 1 1 d . . . . .
O8 O 0.4588(3) 0.25613(12) 0.53703(12) 0.0581(5) Uani 1 1 d . . . . .
H8 H 0.401317 0.296554 0.530950 0.087 Uiso 1 1 calc GR . . . .
O9 O 1.4101(3) 0.61577(13) 0.50891(13) 0.0610(5) Uani 1 1 d . . . . .
O2 O 0.9970(3) 0.56585(16) 0.72007(11) 0.0655(6) Uani 1 1 d . . . . .
O4 O 1.4962(3) 0.15886(14) 0.80144(12) 0.0623(5) Uani 1 1 d . . . . .
N2 N 1.5248(3) 0.43194(15) 0.87732(11) 0.0500(5) Uani 1 1 d . . . . .
O5 O 1.7140(4) 0.20394(17) 0.85333(13) 0.0694(6) Uani 1 1 d . . . . .
N18 N 1.2387(3) 0.38461(15) 0.54733(18) 0.0621(7) Uani 1 1 d . . . . .
C1 C 1.3722(4) 0.44625(16) 0.86090(13) 0.0478(6) Uani 1 1 d . . . . .
H1A H 1.328381 0.497922 0.868972 0.057 Uiso 1 1 calc R . . . .
O6 O 0.6815(5) 0.3283(3) 0.72278(12) 0.1080(14) Uani 1 1 d . . . . .
C21 C 1.0346(3) 0.51827(13) 0.55369(11) 0.0377(5) Uani 1 1 d . . . . .
C9 C 1.2779(3) 0.38713(15) 0.83250(12) 0.0437(5) Uani 1 1 d . . . . .
C4 C 1.4946(3) 0.29364(16) 0.83959(11) 0.0438(5) Uani 1 1 d . . . . .
C27 C 0.6430(3) 0.32895(16) 0.60580(12) 0.0449(5) Uani 1 1 d . . . . .
C12 C 1.0137(4) 0.51360(17) 0.76024(13) 0.0486(6) Uani 1 1 d . . . . .
C20 C 1.1928(3) 0.52822(14) 0.53473(12) 0.0416(5) Uani 1 1 d . . . . .
C11 C 0.9428(3) 0.50680(15) 0.82641(12) 0.0433(5) Uani 1 1 d . . . . .
C13 C 0.8312(4) 0.56978(16) 0.85411(13) 0.0488(6) Uani 1 1 d . . . . .
H13 H 0.745129 0.580419 0.822030 0.059 Uiso 1 1 calc R . . . .
C24 C 0.8104(4) 0.43951(16) 0.59058(13) 0.0472(6) Uani 1 1 d . . . . .
C5 C 1.3384(3) 0.30948(14) 0.82073(11) 0.0421(5) Uani 1 1 d . . . . .
C25 C 0.9824(3) 0.44054(15) 0.56963(12) 0.0437(5) Uani 1 1 d . . . . .
C8 C 1.1089(4) 0.39606(16) 0.80851(14) 0.0488(6) Uani 1 1 d . . . . .
C3 C 1.5810(4) 0.35792(18) 0.86689(12) 0.0489(6) Uani 1 1 d . . . . .
H3 H 1.687533 0.347742 0.878773 0.059 Uiso 1 1 calc R . . . .
C26 C 0.7060(3) 0.37666(16) 0.56048(12) 0.0432(5) Uani 1 1 d . . . . .
H26 H 0.687278 0.371516 0.515287 0.052 Uiso 1 1 calc R . . . .
C00S C 1.5812(4) 0.21478(18) 0.83257(13) 0.0508(6) Uani 1 1 d . . . . .
C14 C 0.9191(5) 0.64911(18) 0.86820(18) 0.0630(8) Uani 1 1 d . . . . .
H14A H 0.843549 0.689708 0.883261 0.094 Uiso 1 1 calc GR . . . .
H14B H 0.970612 0.668139 0.828526 0.094 Uiso 1 1 calc GR . . . .
H14C H 0.998931 0.639917 0.901777 0.094 Uiso 1 1 calc GR . . . .
C10 C 0.9975(3) 0.43902(15) 0.85354(13) 0.0453(5) Uani 1 1 d . . . . .
H10 H 0.969664 0.420571 0.895590 0.054 Uiso 1 1 calc R . . . .
C28 C 0.7054(5) 0.3560(3) 0.66949(14) 0.0639(8) Uani 1 1 d . . . . .
C30 C 0.5263(4) 0.26006(16) 0.60001(16) 0.0527(6) Uani 1 1 d . . . . .
H30 H 0.439567 0.268776 0.632153 0.063 Uiso 1 1 calc R . . . .
C19 C 1.2890(4) 0.45963(17) 0.53247(16) 0.0525(6) Uani 1 1 d . . . . .
H19 H 1.396029 0.466237 0.519740 0.063 Uiso 1 1 calc R . . . .
C00Y C 1.2273(5) 0.74418(18) 0.48927(16) 0.0577(7) Uani 1 1 d . . . . .
H00A H 1.296371 0.738938 0.451388 0.087 Uiso 1 1 calc GR . . . .
H00B H 1.288340 0.764955 0.526003 0.087 Uiso 1 1 calc GR . . . .
H00C H 1.140992 0.781462 0.479278 0.087 Uiso 1 1 calc GR . . . .
C6 C 1.2146(4) 0.25784(17) 0.78704(15) 0.0526(6) Uani 1 1 d . . . . .
H6A H 1.202562 0.205373 0.809259 0.063 Uiso 1 1 calc R . . . .
H6B H 1.243896 0.248091 0.741239 0.063 Uiso 1 1 calc R . . . .
C16 C 1.0861(4) 0.37560(16) 0.56542(17) 0.0562(7) Uani 1 1 d . . . . .
H16 H 1.048416 0.323255 0.575591 0.067 Uiso 1 1 calc R . . . .
C22 C 0.9019(4) 0.57848(15) 0.56156(13) 0.0470(6) Uani 1 1 d . . . . .
H22 H 0.907589 0.635301 0.557079 0.056 Uiso 1 1 calc R . . . .
C012 C 1.2686(4) 0.60669(15) 0.51572(12) 0.0445(6) Uani 1 1 d . . . . .
C7 C 1.0612(4) 0.30743(19) 0.7915(2) 0.0709(10) Uani 1 1 d . . . . .
H7A H 0.991420 0.285164 0.825607 0.085 Uiso 1 1 calc R . . . .
H7B H 1.003989 0.305860 0.749681 0.085 Uiso 1 1 calc R . . . .
C15 C 1.5746(6) 0.0809(2) 0.7932(2) 0.0760(10) Uani 1 1 d . . . . .
H15A H 1.505664 0.044687 0.768650 0.114 Uiso 1 1 calc GR . . . .
H15B H 1.596556 0.057499 0.835874 0.114 Uiso 1 1 calc GR . . . .
H15C H 1.673973 0.088495 0.769658 0.114 Uiso 1 1 calc GR . . . .
C31 C 0.6048(5) 0.1787(2) 0.6144(3) 0.0802(12) Uani 1 1 d . . . . .
H31A H 0.524950 0.136028 0.613246 0.120 Uiso 1 1 calc GR . . . .
H31B H 0.653614 0.180345 0.657463 0.120 Uiso 1 1 calc GR . . . .
H31C H 0.685997 0.167784 0.581712 0.120 Uiso 1 1 calc GR . . . .
C23 C 0.7562(5) 0.52789(19) 0.5783(3) 0.0805(13) Uani 1 1 d . . . . .
H23 H 0.650781 0.547110 0.580826 0.097 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C012 O10 C00Y 115.8(2) . . ?
C12 O3 C8 109.8(2) . . ?
C28 O7 C24 109.0(2) . . ?
C00S O4 C15 115.2(3) . . ?
C3 N2 C1 117.4(2) . . ?
C16 N18 C19 117.7(2) . . ?
N2 C1 C9 121.8(3) . . ?
C20 C21 C22 131.3(2) . . ?
C25 C21 C20 118.2(2) . . ?
C25 C21 C22 110.4(2) . . ?
C1 C9 C5 120.6(3) . . ?
C1 C9 C8 127.3(2) . . ?
C5 C9 C8 112.0(2) . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 C00S 126.5(3) . . ?
C3 C4 C00S 116.3(3) . . ?
C26 C27 C28 107.3(3) . . ?
C26 C27 C30 130.7(3) . . ?
C28 C27 C30 122.0(3) . . ?
O3 C12 C11 108.3(2) . . ?
O2 C12 O3 122.4(3) . . ?
O2 C12 C11 129.3(3) . . ?
C21 C20 C012 125.5(2) . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 C012 116.6(3) . . ?
C12 C11 C13 122.7(2) . . ?
C10 C11 C12 107.8(2) . . ?
C10 C11 C13 129.5(3) . . ?
O1 C13 C11 111.2(2) . . ?
O1 C13 C14 107.5(2) . . ?
C11 C13 C14 111.0(3) . . ?
O7 C24 C25 108.8(2) . . ?
O7 C24 C26 103.4(2) . . ?
O7 C24 C23 110.2(3) . . ?
C25 C24 C23 103.0(2) . . ?
C26 C24 C25 117.0(2) . . ?
C26 C24 C23 114.5(3) . . ?
C9 C5 C6 110.2(3) . . ?
C4 C5 C9 117.8(2) . . ?
C4 C5 C6 132.0(2) . . ?
C21 C25 C24 112.2(2) . . ?
C16 C25 C21 119.9(3) . . ?
C16 C25 C24 127.8(2) . . ?
O3 C8 C9 108.2(2) . . ?
O3 C8 C10 103.1(2) . . ?
O3 C8 C7 111.9(3) . . ?
C9 C8 C7 102.9(2) . . ?
C10 C8 C9 115.8(2) . . ?
C10 C8 C7 115.0(3) . . ?
N2 C3 C4 125.1(3) . . ?
C27 C26 C24 111.0(2) . . ?
O4 C00S C4 112.8(3) . . ?
O5 C00S O4 124.3(3) . . ?
O5 C00S C4 123.0(3) . . ?
C11 C10 C8 110.9(2) . . ?
O7 C28 C27 109.4(2) . . ?
O6 C28 O7 121.6(3) . . ?
O6 C28 C27 129.0(4) . . ?
O8 C30 C27 111.7(2) . . ?
O8 C30 C31 108.1(3) . . ?
C27 C30 C31 111.5(3) . . ?
N18 C19 C20 124.0(3) . . ?
C5 C6 C7 104.6(2) . . ?
N18 C16 C25 122.2(3) . . ?
C21 C22 C23 105.0(2) . . ?
O10 C012 C20 112.6(2) . . ?
O9 C012 O10 123.5(2) . . ?
O9 C012 C20 123.9(3) . . ?
C6 C7 C8 107.4(3) . . ?
C22 C23 C24 108.4(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O10 C00Y 1.442(3) . ?
O10 C012 1.332(4) . ?
O3 C12 1.360(4) . ?
O3 C8 1.464(4) . ?
O1 C13 1.410(4) . ?
O7 C24 1.461(4) . ?
O7 C28 1.354(5) . ?
O8 C30 1.407(4) . ?
O9 C012 1.204(4) . ?
O2 C12 1.196(4) . ?
O4 C00S 1.325(4) . ?
O4 C15 1.449(4) . ?
N2 C1 1.343(4) . ?
N2 C3 1.322(4) . ?
O5 C00S 1.204(5) . ?
N18 C19 1.338(4) . ?
N18 C16 1.339(5) . ?
C1 C9 1.380(4) . ?
O6 C28 1.197(4) . ?
C21 C20 1.391(4) . ?
C21 C25 1.390(3) . ?
C21 C22 1.498(3) . ?
C9 C5 1.395(4) . ?
C9 C8 1.506(4) . ?
C4 C5 1.389(4) . ?
C4 C3 1.398(4) . ?
C4 C00S 1.493(4) . ?
C27 C26 1.323(4) . ?
C27 C28 1.471(4) . ?
C27 C30 1.501(4) . ?
C12 C11 1.480(4) . ?
C20 C19 1.387(4) . ?
C20 C012 1.489(3) . ?
C11 C13 1.506(4) . ?
C11 C10 1.326(4) . ?
C13 C14 1.525(4) . ?
C24 C25 1.504(4) . ?
C24 C26 1.487(4) . ?
C24 C23 1.543(4) . ?
C5 C6 1.506(4) . ?
C25 C16 1.379(4) . ?
C8 C10 1.488(4) . ?
C8 C7 1.551(4) . ?
C30 C31 1.520(4) . ?
C6 C7 1.525(5) . ?
C22 C23 1.516(5) . ?
