Phloroglucinol Derivatives with Unusual Skeletons from Cleistocalyx operculatus and Their in Vitro Antiviral Activity.
Su, Jun-Cheng; Wang, Shan; Cheng, Wen; Huang, Xiao-Jun; Li, Man-Mei; Jiang, Ren-Wang; Li, Yao-Lan; Wang, Lei; Ye, Wen-Cai; Wang, Ying; The Journal of organic chemistry 83 (2018) 8522–8532; doi:10.1021/acs.joc.8b01050

data_4035592
_publ_section_title
;
 Phloroglucinol Derivatives with Unusual Skeletons from Cleistocalyx
 operculatus and Their in Vitro Antiviral Activity.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8522
_journal_page_last               8532
_journal_paper_doi               10.1021/acs.joc.8b01050
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C1 H1 Cl3, 3(C36 H34 O8)'
_chemical_formula_sum            'C109 H103 Cl3 O24'
_chemical_formula_weight         1903.26
_chemical_name_systematic        'cleistoperlone B'
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-09-07 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                120.0
_cell_formula_units_Z            3
_cell_length_a                   30.9223(3)
_cell_length_b                   30.9223(3)
_cell_length_c                   8.33380(10)
_cell_measurement_reflns_used    21534
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4300
_cell_measurement_theta_min      4.9170
_cell_volume                     6901.08(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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   -117.00 -54.00   1.00    1.00    --  -40.46-153.00 130.00   63
  2  \w   -119.00  -7.00   1.00    1.00    --  -40.46 -77.00   0.00  112
  3  \w     11.00 114.00   1.00    1.00    --   40.46  57.00  90.00  103
  4  \w     14.00 117.00   1.00    1.00    --   40.46  37.00 150.00  103
  5  \w      1.00  28.00   1.00    1.00    --   40.46  92.00  16.04   27
  6  \w      7.00 119.00   1.00    1.00    --   40.46  77.00  60.00  112
  7  \w     23.00  98.00   1.00    1.00    --   40.46-125.00-180.00   75
  8  \w     74.00 178.00   1.00    2.86    --  107.48  77.00   0.00  104
  9  \w     77.00 178.00   1.00    2.86    --  107.48  61.00  60.00  101
 10  \w     33.00 135.00   1.00    2.86    --  107.48 -45.00  60.00  102
 11  \w     74.00 178.00   1.00    2.86    --  107.48  77.00  30.00  104
 12  \w     74.00 178.00   1.00    2.86    --  107.48  77.00  60.00  104
 13  \w     80.00 178.00   1.00    2.86    --  107.48  45.00  60.00   98
 14  \w    100.00 178.00   1.00    2.86    --  107.48 111.00-180.00   78
 15  \w     80.00 178.00   1.00    2.86    --  107.48  45.00  30.00   98
 16  \w     77.00 178.00   1.00    2.86    --  107.48  61.00   0.00  101
 17  \w     80.00 178.00   1.00    2.86    --  107.48  45.00  90.00   98
 18  \w     77.00 178.00   1.00    2.86    --  107.48  61.00  30.00  101
 19  \w    100.00 178.00   1.00    2.86    --  107.48 111.00-150.00   78
 20  \w   -117.00 -29.00   1.00    1.00    --  -40.46 -37.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0045093000
_diffrn_orient_matrix_UB_12      -0.0453447000
_diffrn_orient_matrix_UB_13      -0.0527629000
_diffrn_orient_matrix_UB_21      -0.0552793000
_diffrn_orient_matrix_UB_22      -0.0274150000
_diffrn_orient_matrix_UB_23      -0.0513616000
_diffrn_orient_matrix_UB_31      0.0153151000
_diffrn_orient_matrix_UB_32      0.0224416000
_diffrn_orient_matrix_UB_33      -0.1694617000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24819
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.696
_diffrn_reflns_theta_min         4.954
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       blocks
_exptl_crystal_F_000             3000
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2858 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(4)
_refine_ls_extinction_coef       0.00017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+3.7650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                5953
_reflns_number_total             5961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01050_si_003.cif
_cod_data_source_block           sw-a8-f2
_cod_original_cell_volume        6901.08(12)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4035592
_shelx_shelxl_version_number     2016/6
_cell_oxdiff_angle_alpha         89.9871(16)
_cell_oxdiff_angle_beta          90.0491(15)
_cell_oxdiff_angle_gamma         119.9888(19)
_cell_oxdiff_length_a            30.9144(5)
_cell_oxdiff_length_b            30.9135(6)
_cell_oxdiff_length_c            8.33736(17)
_cell_oxdiff_measurement_reflns_used 21679
_cell_oxdiff_volume              6901.1(2)
_reflns_odcompleteness_completeness 99.96
_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:
 C9'(H9'), C1S(H1S)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C8'(H8'a,H8'b)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C11'(H11'),
 C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15')
2.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C16'(H16c,H16d,H16e), C17'(H17d,
 H17e,H17f), C18'(H18d,H18e,H18f)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4'(H4')
;
_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 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.666