Lonimacranaldes A–C, three iridoids with novel skeletons from Lonicera macranthoides
Mei, Yu-Dan; Li, Hai-Bo; Pang, Qian-Qian; Li, Ting; Pan, Da-Bo; Dai, Yi; Qin, Da-Peng; Meng, He; Yao, Xin-Sheng; Yu, Yang; RSC Advances 9 (2019) 22011–; doi:10.1039/C9RA04029C

data_7233173
_publ_section_title
;
 Lonimacranaldes A--C, three iridoids with novel skeletons from Lonicera
 macranthoides
;
_journal_issue                   38
_journal_name_full               'RSC Advances'
_journal_page_first              22011
_journal_paper_doi               10.1039/C9RA04029C
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H30 O10, C2 H6 O'
_chemical_formula_sum            'C24 H36 O11'
_chemical_formula_weight         500.53
_chemical_name_systematic        'lonimacranaldes A'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-11-07 deposited with the CCDC.    2019-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.561(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1270(2)
_cell_length_b                   7.98020(10)
_cell_length_c                   13.2754(2)
_cell_measurement_reflns_used    19373
_cell_measurement_temperature    149.94(10)
_cell_measurement_theta_max      73.8090
_cell_measurement_theta_min      3.8890
_cell_volume                     1243.91(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.94(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -22.00  89.00   0.50    0.50    --    0.00  57.00 150.00  222
  2  \w    -29.00  89.00   0.50    0.50    --    0.00  77.00  90.00  236
  3  \w    -22.00  89.00   0.50    0.50    --    0.00  57.00 -60.00  222
  4  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00 120.00  242
  5  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00 -90.00  242
  6  \w      6.00 119.00   0.50    0.50    --   95.20 -61.00  30.00  226
  7  \w     66.00 185.00   0.50    0.50    --   95.20  77.00 120.00  238
  8  \w     64.00 185.00   0.50    0.50    --   95.20  82.00  60.00  242
  9  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00  30.00  242
 10  \w      6.00 119.00   0.50    0.50    --   95.20 -61.00  90.00  226
 11  \w     76.00 185.00   0.50    0.50    --   95.20  45.00   0.00  218
 12  \w     79.00 185.00   0.50    0.50    --   95.20  30.00 -60.00  212
 13  \w     72.00 185.00   0.50    0.50    --   95.20  15.00-150.00  226
 14  \w      6.00 119.00   0.50    0.50    --   95.20 -61.00-120.00  226
 15  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00-180.00  242
 16  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00 -30.00  242
 17  \w     64.00 185.00   0.50    0.50    --   95.20  82.00  90.00  242
 18  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00  60.00  212
 19  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00 -90.00  212
 20  \w    -22.00  89.00   0.50    0.50    --    0.00  57.00   0.00  222
 21  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00-120.00  212
 22  \w     76.00 185.00   0.50    0.50    --   95.20  45.00 -30.00  218
 23  \w     76.00 185.00   0.50    0.50    --   95.20  45.00-120.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0241833000
_diffrn_orient_matrix_UB_12      0.0100556000
_diffrn_orient_matrix_UB_13      -0.1245412000
_diffrn_orient_matrix_UB_21      0.0207064000
_diffrn_orient_matrix_UB_22      0.1905944000
_diffrn_orient_matrix_UB_23      0.0117959000
_diffrn_orient_matrix_UB_31      0.1273022000
_diffrn_orient_matrix_UB_32      -0.0292586000
_diffrn_orient_matrix_UB_33      0.0341716000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23017
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.164
_diffrn_reflns_theta_min         3.722
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0444P)^2^+0.3986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                4804
_reflns_number_total             4915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra04029c2.cif
_cod_data_source_block           d2a
_cod_original_cell_volume        1243.90(4)
_cod_database_code               7233173
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.878
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C1"(H1"A), C9(H9), C5"(H5"), C3"(H3"A), C4'(H4'), C8(H8), C2"(H2"A),
 C4"(H4"A), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C6"(H6"A,H6"B), C6(H6A,H6B), C5'(H5'A,H5'B), C2S(H2SA,H2SB)
2.c Aromatic/amide H refined with riding coordinates:
 C3'(H3'), C3(H3A), C1'(H1')
2.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C6'(H6'A,H6'B,H6'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3"(H3"), O1"(H1"), O4"(H4"), O3(H3), O2"(H2")
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.454
_oxdiff_exptl_absorpt_empirical_full_min 0.463