Propolis Components from Stingless Bees Collected on South Sulawesi, Indonesia, and Their Xanthine Oxidase Inhibitory Activity.
Miyata, Ryo; Sahlan, Muhamad; Ishikawa, Yoshinobu; Hashimoto, Hiroshi; Honda, Sari; Kumazawa, Shigenori; Journal of natural products 82 (2019) 205–210; doi:10.1021/acs.jnatprod.8b00541

data_1552644
_publ_section_title
;
 Propolis Components from Stingless Bees Collected on South Sulawesi,
 Indonesia, and Their Xanthine Oxidase Inhibitory Activity.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              205
_journal_page_last               210
_journal_paper_doi               10.1021/acs.jnatprod.8b00541
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 O7'
_chemical_formula_sum            'C22 H22 O7'
_chemical_formula_weight         398.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.3730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.01570(10)
_cell_length_b                   6.75950(10)
_cell_length_c                   13.03660(10)
_cell_measurement_reflns_used    18609
_cell_measurement_temperature    100.2(5)
_cell_measurement_theta_max      75.9990
_cell_measurement_theta_min      3.5260
_cell_volume                     931.348(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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      100.2(5)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     20.00 120.00   0.50    0.26    --   42.55  38.00 -60.00  200
  2  \w     88.00 178.00   0.50    0.59    --  111.75  61.00   0.00  180
  3  \w     88.00 178.00   0.50    0.59    --  111.75  61.00  90.00  180
  4  \w     88.00 178.00   0.50    0.59    --  111.75  61.00  30.00  180
  5  \w     83.00 178.00   0.50    0.59    --  111.75  77.00  30.00  190
  6  \w     83.00 178.00   0.50    0.59    --  111.75  77.00 -60.00  190
  7  \w     90.00 178.00   0.50    0.59    --  111.75  45.00  90.00  176
  8  \w     90.00 178.00   0.50    0.59    --  111.75  45.00 -30.00  176
  9  \w     83.00 178.00   0.50    0.59    --  111.75  77.00-180.00  190
 10  \w     83.00 178.00   0.50    0.59    --  111.75  77.00 -30.00  190
 11  \w     92.00 178.00   0.50    0.59    --  111.75 125.00 120.00  172
 12  \w     83.00 178.00   0.50    0.59    --  111.75  77.00   0.00  190
 13  \w     88.00 178.00   0.50    0.59    --  111.75  61.00 -60.00  180
 14  \w     92.00 178.00   0.50    0.59    --  111.75 125.00-180.00  172
 15  \w     88.00 178.00   0.50    0.59    --  111.75  61.00 -30.00  180
 16  \w     83.00 178.00   0.50    0.59    --  111.75  77.00  60.00  190
 17  \w     90.00 178.00   0.50    0.59    --  111.75  45.00 -90.00  176
 18  \w     83.00 178.00   0.50    0.59    --  111.75  77.00-120.00  190
 19  \w     90.00 178.00   0.50    0.59    --  111.75  45.00-120.00  176
 20  \w     60.00 121.00   0.50    0.26    --   42.55 178.00  30.00  122
 21  \w     60.00 121.00   0.50    0.26    --   42.55 178.00  90.00  122
 22  \w     83.00 178.00   0.50    0.59    --  111.75  77.00 150.00  190
 23  \w     83.00 178.00   0.50    0.59    --  111.75  77.00 120.00  190
 24  \w     38.00 108.00   0.50    0.59    --  111.75 -94.00 120.00  140
 25  \w     38.00 108.00   0.50    0.59    --  111.75 -94.00 150.00  140
 26  \w     38.00 108.00   0.50    0.59    --  111.75 -94.00  90.00  140
 27  \w     38.00 108.00   0.50    0.59    --  111.75 -94.00  30.00  140
 28  \w     57.00 123.00   0.50    0.26    --   42.55-178.00 -90.00  132
 29  \w     57.00 123.00   0.50    0.26    --   42.55-178.00  60.00  132
 30  \w     38.00 121.00   0.50    0.59    --  111.75-125.00  60.00  166
 31  \w     38.00 108.00   0.50    0.59    --  111.75 -94.00 -60.00  140
 32  \w     38.00 141.00   0.50    0.59    --  111.75 -77.00-150.00  206
 33  \w     61.00 178.00   0.50    0.59    --  111.75  15.00-180.00  234
 34  \w     38.00 108.00   0.50    0.59    --  111.75 -94.00-180.00  140
 35  \w     20.00 120.00   0.50    0.26    --   42.55  38.00-150.00  200
 36  \w     21.00 116.00   0.50    0.26    --   42.55  57.00 -30.00  190
 37  \w     14.00 116.00   0.50    0.26    --   42.55  77.00-150.00  204
 38  \w    -64.00  32.00   0.50    0.26    --  -42.55  57.00 150.00  192
 39  \w    -95.00 -16.00   0.50    0.59    --  -90.25 125.00-150.00  158
 40  \w   -116.00 -20.00   0.50    0.26    --  -42.55 -57.00-120.00  192
 41  \w   -116.00 -14.00   0.50    0.26    --  -42.55 -77.00  30.00  204
 42  \w   -116.00 -14.00   0.50    0.26    --  -42.55 -77.00  60.00  204
 43  \w   -116.00 -20.00   0.50    0.26    --  -42.55 -57.00 120.00  192
 44  \w   -116.00 -14.00   0.50    0.26    --  -42.55 -77.00 120.00  204
 45  \w   -164.00 -66.00   0.50    0.59    --  -90.25 -66.00 -11.21  196
 46  \w   -116.00 -20.00   0.50    0.26    --  -42.55 -57.00-180.00  192
 47  \w   -164.00 -67.00   0.50    0.59    --  -90.25 -61.00  30.00  194
 48  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00  30.00  206
 49  \w   -164.00 -66.00   0.50    0.59    --  -90.25 -66.00 -31.51  196
 50  \w   -164.00 -68.00   0.50    0.59    --  -90.25 -59.00 -14.89  192
 51  \w   -163.00 -67.00   0.50    0.59    --  -90.25 -62.00 -64.28  192
 52  \w   -164.00 -62.00   0.50    0.59    --  -90.25 -74.00  52.42  204
 53  \w   -164.00 -64.00   0.50    0.59    --  -90.25 -69.00  23.74  200
 54  \w   -163.00 -69.00   0.50    0.59    --  -90.25 -54.00 -82.14  188
 55  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00   0.00  206
 56  \w   -164.00 -69.00   0.50    0.59    --  -90.25 -53.00  30.44  190
 57  \w   -164.00 -67.00   0.50    0.59    --  -90.25 -61.00  60.00  194
 58  \w   -164.00 -68.00   0.50    0.59    --  -90.25 -60.00  -3.63  192
 59  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00 -30.00  206
 60  \w   -165.00 -68.00   0.50    0.59    --  -90.25 -50.00 -54.64  194
 61  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00 -60.00  206
 62  \w   -164.00 -62.00   0.50    0.59    --  -90.25 -74.00-136.69  204
 63  \w   -164.00 -62.00   0.50    0.59    --  -90.25 -76.00-156.36  204
 64  \w   -164.00 -59.00   0.50    0.59    --  -90.25 -81.00 -93.32  210
 65  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00  90.00  206
 66  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00 150.00  206
 67  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00 113.79  206
 68  \w   -164.00 -61.00   0.50    0.59    --  -90.25 -77.00-180.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1253450000
_diffrn_orient_matrix_UB_12      0.0666281000
_diffrn_orient_matrix_UB_13      -0.0793442000
_diffrn_orient_matrix_UB_21      -0.0656202000
_diffrn_orient_matrix_UB_22      -0.0110494000
_diffrn_orient_matrix_UB_23      0.0897362000
_diffrn_orient_matrix_UB_31      0.0349809000
_diffrn_orient_matrix_UB_32      0.2176410000
_diffrn_orient_matrix_UB_33      0.0288493000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37659
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.620
_diffrn_reflns_theta_min         3.534
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.421
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1679 quotients [(I+)-(I-)]/[(I+)+(I-)] on PLATON
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0515P)^2^+0.1459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3683
_reflns_number_total             3800
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00541_si_002.cif
_cod_data_source_block           exp_1007
_cod_database_code               1552644
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C22 H22 O7'
_chemical_oxdiff_usercomment     'ishikawa 1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
2.a Ternary CH refined with riding coordinates:
 C18(H18), C17(H17), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C7(H7A,H7B), C9(H9A,H9B), C19(H19A,H19B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C12(H12)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              4355
_shelx_hkl_checksum              58181
_olex2_submission_original_sample_id 'ishikawa 1'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.545