Secoiridoids and Iridoids from <i>Morinda asteroscepa</i>.
Zandi, Linda; Makungu, Marco; Munissi, Joan J. E.; Duffy, Sandra; Puttreddy, Rakesh; von der Heiden, Daniel; Rissanen, Kari; Avery, Vicky M.; Nyandoro, Stephen S.; Erdélyi, Máté; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.0c00447

data_1558928
_publ_section_title
;
 Secoiridoids and Iridoids from <i>Morinda asteroscepa</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00447
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H18 O7'
_chemical_formula_sum            'C11 H18 O7'
_chemical_formula_weight         262.25
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-03
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.39944(5)
_cell_length_b                   11.11572(8)
_cell_length_c                   15.42283(10)
_cell_measurement_reflns_used    18449
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.3180
_cell_measurement_theta_min      3.9630
_cell_volume                     1268.529(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   18.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   37.0000   60.0000 26

  2 omega   59.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   37.0000   60.0000 36

  3 omega  114.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   62.0000   48.6314 64

  4 omega  150.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 26

  5 omega  144.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 34

  6 omega  117.00  143.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 26

  7 omega   86.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 26

  8 omega   88.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 26

  9 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   62.0000   48.6314 26

 10 omega   83.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 95

 11 omega  124.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 54

 12 omega   86.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 27

 13 omega   80.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   74.0000  -49.7338 25

 14 omega   83.00  118.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 35

 15 omega   84.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 82

 16 omega   80.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 26

 17 omega   85.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   52.0000 -155.8780 40

 18 omega   84.00  152.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 68

 19 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 26

 20 omega   84.00  158.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 74

 21 omega   79.00  155.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 76

 22 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 26

 23 omega   83.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 27

 24 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 26

 25 omega   81.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   72.0000  114.6848 26

 26 omega   86.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   57.0000   83.1190 43

 27 omega   83.00  160.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 77

 28 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 26

 29 omega   82.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   65.0000  104.8880 37

 30 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26

 31 omega   80.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 33

 32 omega   80.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 26

 33 omega   83.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 27

 34 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 26

 35 omega   80.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 26

 36 omega   58.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -150.0000 84

 37 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   37.0000  -60.0000 99

 38 omega   40.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 54

 39 omega   36.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 80

 40 omega   47.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 56

 41 omega   32.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 60

 42 omega   36.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 77

 43 omega  114.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 26

 44 omega   37.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 49

 45 omega    1.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676  -99.0000   30.0000 71

 46 omega    2.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676  -99.0000  120.0000 79

 47 omega   14.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   57.0000   30.0000 39

 48 omega   11.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   77.0000   60.0000 87

 49 omega   10.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   77.0000  150.0000 108

 50 omega    5.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   88.0000 -119.9948 25

 51 omega  -41.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -150.0000 73

 52 omega  -56.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000 -180.0000 43

 53 omega  -61.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000  -90.0000 52

 54 omega  -89.00  -60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000 -180.0000 29

 55 omega -116.00  -91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000  -90.0000 25

 56 omega  -69.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   57.0000  -60.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0806431000
_diffrn_orient_matrix_UB_12      -0.0835388000
_diffrn_orient_matrix_UB_13      0.0696355000
_diffrn_orient_matrix_UB_21      0.1886186000
_diffrn_orient_matrix_UB_22      -0.0148850000
_diffrn_orient_matrix_UB_23      0.0409662000
_diffrn_orient_matrix_UB_31      -0.0359826000
_diffrn_orient_matrix_UB_32      0.1095234000
_diffrn_orient_matrix_UB_33      0.0587400000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18210
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.645
_diffrn_reflns_theta_max         66.645
_diffrn_reflns_theta_min         4.904
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72726
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2338
_exptl_crystal_size_mid          0.2049
_exptl_crystal_size_min          0.2033
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0542P)^2^+0.2005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2249
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00447_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        1268.528(15)
_cod_database_code               1558928
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H20 O3'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H4 of O4, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H3 of O3, H2 of O2, H5 of O5
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5A), C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'