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_4035593
_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_formula_moiety         'C36 H34 O8'
_chemical_formula_sum            'C36 H34 O8'
_chemical_formula_weight         594.63
_chemical_name_systematic        'cleistoperlone A'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-01
_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                 96.1889(11)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   24.7977(3)
_cell_length_b                   13.25910(16)
_cell_length_c                   18.0031(2)
_cell_measurement_reflns_used    7694
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8550
_cell_measurement_theta_min      3.7690
_cell_volume                     5884.83(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_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    -66.00  24.00   1.00    2.11    --  -41.89  37.00  30.00   90
  2  \w     25.00  80.00   1.00    2.11    --   41.89-125.00-150.00   55
  3  \w     60.00 125.00   1.00    8.45    --  107.79 -77.00 -90.00   65
  4  \w    108.00 135.00   1.00    8.45    --  107.79 -30.00-120.00   27
  5  \w     84.00 178.00   1.00    8.45    --  107.79  45.00  60.00   94
  6  \w     94.00 162.00   1.00    8.45    --  107.79 125.00 -60.00   68
  7  \w     88.00 164.00   1.00    8.45    --  107.79  45.00 120.00   76
  8  \w     86.00 114.00   1.00    8.45    --  107.79 -30.00  90.00   28
  9  \w     37.00  65.00   1.00    8.45    --  107.79 -30.00  90.00   28
 10  \w     36.00  63.00   1.00    8.45    --  107.79 -30.00-120.00   27
 11  \w   -116.00 -21.00   1.00    2.11    --  -41.89 -37.00-150.00   95
;
_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      0.0221603000
_diffrn_orient_matrix_UB_12      0.0642438000
_diffrn_orient_matrix_UB_13      -0.0612094000
_diffrn_orient_matrix_UB_21      0.0563324000
_diffrn_orient_matrix_UB_22      -0.0483224000
_diffrn_orient_matrix_UB_23      0.0185014000
_diffrn_orient_matrix_UB_31      -0.0154849000
_diffrn_orient_matrix_UB_32      -0.0839448000
_diffrn_orient_matrix_UB_33      -0.0575792000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11304
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.075
_diffrn_reflns_theta_min         3.586
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_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^+3.7402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5305
_reflns_number_total             5796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01050_si_002.cif
_cod_data_source_block           1607078
_cod_original_cell_volume        5884.84(12)
_cod_database_code               4035593
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C20 H20 N4 O4'
_chemical_oxdiff_usercomment     SW-99
_cell_oxdiff_angle_alpha         90.040(2)
_cell_oxdiff_angle_beta          96.166(2)
_cell_oxdiff_angle_gamma         90.008(2)
_cell_oxdiff_length_a            24.7989(6)
_cell_oxdiff_length_b            13.2546(4)
_cell_oxdiff_length_c            18.0077(5)
_cell_oxdiff_measurement_reflns_used 7697
_cell_oxdiff_volume              5884.8(3)
_reflns_odcompleteness_completeness 99.98
_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')
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), 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 Tetrahedral OH refined with riding coordinates:
 O4'(H4')
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C16'(H16D,H16E,H16F), C17'(H17C,
 H17D,H17E), C18'(H18D,H18E,H18F)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.753