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_4035595
_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_compound_source        'Cleistocalyx operculatus'
_chemical_formula_moiety         'C28 H32 O4'
_chemical_formula_sum            'C28 H32 O4'
_chemical_formula_weight         432.53
_chemical_name_common            'operculatol A'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2018-04-16 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                112.387(5)
_cell_angle_beta                 105.710(4)
_cell_angle_gamma                92.527(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2778(4)
_cell_length_b                   10.3228(5)
_cell_length_c                   12.3658(6)
_cell_measurement_reflns_used    9128
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      73.3580
_cell_measurement_theta_min      4.0510
_cell_volume                     1151.68(11)
_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      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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     -1.00  24.00   1.00    1.00    --   38.00  94.00-117.76   25
  2  \w     -1.00  24.00   1.00    1.00    --   38.00  94.00  31.97   25
  3  \w   -112.00 -60.00   1.00    1.00    --  -40.23 -57.00-120.00   52
  4  \w    -62.00  34.00   1.00    1.00    --  -40.23  37.00 -60.00   96
  5  \w    -63.00  34.00   1.00    1.00    --  -40.23  37.00  30.00   97
  6  \w    -43.00 -12.00   1.00    1.00    --  -40.23 -57.00-120.00   31
  7  \w     59.00  89.00   1.00    1.00    --   40.23  37.00   0.00   30
  8  \w     18.00  55.00   1.00    1.00    --   40.23  37.00   0.00   37
  9  \w     51.00  95.00   1.00    1.00    --   40.23-125.00  30.00   44
 10  \w     32.00  89.00   1.00    1.00    --   40.23-125.00-180.00   57
 11  \w      9.00  34.00   1.00    1.00    --   42.00  79.00 123.46   25
 12  \w     12.00  39.00   1.00    1.00    --   46.00  82.00 -59.58   27
 13  \w     17.00  42.00   1.00    1.00    --   50.00  80.00 116.36   25
 14  \w     21.00  47.00   1.00    1.00    --   54.00  79.00 157.05   26
 15  \w     21.00  46.00   1.00    1.00    --   54.00  78.00  50.58   25
 16  \w     21.00  46.00   1.00    1.00    --   54.00  78.00 -16.67   25
 17  \w     27.00  57.00   1.00    1.00    --   58.00  75.00-149.74   30
 18  \w     76.00 133.00   1.00    1.00    --   58.00  75.00-149.74   57
 19  \w     88.00 138.00   1.00    1.00    --   62.00  77.00 -73.88   50
 20  \w     30.00  56.00   1.00    1.00    --   62.00  77.00 -73.88   26
 21  \w     33.00  70.00   1.00    1.00    --   66.00  77.00  33.91   37
 22  \w     34.00  74.00   1.00    1.00    --   66.00  75.00-118.48   40
 23  \w    109.00 141.00   1.00    1.00    --   66.00  75.00-118.48   32
 24  \w     37.00  65.00   1.00    1.00    --   70.00  77.00  73.77   28
 25  \w     39.00  77.00   1.00    1.00    --   70.00  77.00 -11.55   38
 26  \w     78.00 144.00   1.00    1.00    --   70.00  77.00 -11.55   66
 27  \w     38.00  65.00   1.00    1.00    --   70.00  77.00 -58.33   27
 28  \w     42.00  82.00   1.00    1.00    --   74.00  77.00 129.89   40
 29  \w     41.00  78.00   1.00    1.00    --   74.00  77.00 161.34   37
 30  \w     42.00  68.00   1.00    1.00    --   74.00  76.00 110.00   26
 31  \w     80.00 111.00   1.00    1.53    --  108.20  61.00-150.00   31
 32  \w     76.00 112.00   1.00    1.53    --  108.20  77.00   0.00   36
 33  \w     28.00 107.00   1.00    1.53    --  108.20 -94.00-150.00   79
 34  \w     77.00 102.00   1.00    1.53    --  108.20  77.00-120.00   25
 35  \w     79.00 149.00   1.00    1.53    --  108.20  77.00 -30.00   70
 36  \w     76.00 103.00   1.00    1.53    --  108.20  77.00 150.00   27
 37  \w     77.00 107.00   1.00    1.53    --  108.20  77.00 -90.00   30
 38  \w     27.00 104.00   1.00    1.53    --  108.20 -94.00 -30.00   77
 39  \w     76.00 142.00   1.00    1.53    --  108.20  77.00-180.00   66
 40  \w     79.00 156.00   1.00    1.53    --  108.20  61.00  30.00   77
 41  \w     26.00  83.00   1.00    1.53    --  108.20 -94.00-180.00   57
 42  \w     82.00 152.00   1.00    1.53    --  108.20  61.00-120.00   70
 43  \w     77.00 177.00   1.00    1.53    --  108.20  77.00 120.00  100
 44  \w     76.00 146.00   1.00    1.53    --  108.20  77.00 -60.00   70
 45  \w     81.00 108.00   1.00    1.53    --  108.20  61.00 -60.00   27
 46  \w    132.00 174.00   1.00    1.53    --  108.20  61.00   0.00   42
 47  \w     85.00 113.00   1.00    1.53    --  108.20  61.00   0.00   28
 48  \w     77.00 115.00   1.00    1.53    --  108.20  77.00-150.00   38
 49  \w    123.00 156.00   1.00    1.53    --  108.20  61.00  90.00   33
 50  \w     79.00 177.00   1.00    1.53    --  108.20  61.00  60.00   98
 51  \w     80.00 137.00   1.00    1.53    --  108.20  61.00 -90.00   57
 52  \w    115.00 177.00   1.00    1.53    --  108.20  77.00 -90.00   62
 53  \w     79.00 110.00   1.00    1.53    --  108.20  61.00  90.00   31
 54  \w    124.00 151.00   1.00    1.53    --  108.20  77.00 150.00   27
 55  \w     67.00 104.00   1.00    1.53    --  108.20 -45.00 -60.00   37
 56  \w     81.00 118.00   1.00    1.53    --  108.20  61.00-180.00   37
 57  \w     27.00 105.00   1.00    1.53    --  108.20 -94.00 -90.00   78
 58  \w     96.00 178.00   1.00    1.53    --  108.20 125.00-180.00   82
 59  \w     35.00 120.00   1.00    1.53    --  108.20-125.00 150.00   85
 60  \w     79.00 118.00   1.00    1.53    --  108.20  61.00 120.00   39
 61  \w     39.00  71.00   1.00    1.00    --   70.00  75.00-168.78   32
 62  \w    120.00 145.00   1.00    1.00    --   70.00  75.00-168.78   25
 63  \w     43.00  69.00   1.00    1.00    --   74.00  77.00-105.70   26
 64  \w     74.00 100.00   1.00    1.53    --  106.95  77.00  90.00   26
 65  \w     74.00  99.00   1.00    1.53    --  106.95  77.00-120.00   25
 66  \w   -113.00 -14.00   1.00    1.00    --  -41.23 -53.00 -23.00   99
 67  \w    -47.00 129.00   1.00    1.00    --   41.23   0.00  30.00  176
 68  \w    -47.00 129.00   1.00    1.00    --   41.23   0.00  90.00  176
 69  \w    -47.00 129.00   1.00    1.00    --   41.23   0.00   0.00  176
 70  \w    -47.00 129.00   1.00    1.00    --   41.23   0.00 -90.00  176
 71  \w      0.00 121.00   1.00    1.00    --   41.23  19.00 -90.00  121
 72  \w    -47.00 129.00   1.00    1.00    --   41.23   0.00 -60.00  176
 73  \w    -47.00  97.00   1.00    1.00    --   41.23   0.00 120.00  144
;
_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      -0.1149181000
_diffrn_orient_matrix_UB_12      0.0081959000
_diffrn_orient_matrix_UB_13      0.0594127000
_diffrn_orient_matrix_UB_21      0.0446441000
_diffrn_orient_matrix_UB_22      0.1621579000
_diffrn_orient_matrix_UB_23      0.0691797000
_diffrn_orient_matrix_UB_31      -0.0986299000
_diffrn_orient_matrix_UB_32      0.0205201000
_diffrn_orient_matrix_UB_33      -0.1085659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1720
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20635
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.134
_diffrn_reflns_theta_min         4.069
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63657
_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_colour_primary    yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Flack x determined using 2934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         8524
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0748
_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^)+(0.1287P)^2^+0.4106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2073
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.840
_reflns_number_gt                7669
_reflns_number_total             8524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01050_si_004.cif
_cod_data_source_block           sw_14
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1151.68(10)
_cod_original_formula_moiety     '2(C28 H32 O4)'
_cod_original_formula_sum        'C56 H64 O8'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     865.07
_cod_database_code               4035595
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.95
_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'), C3'(H3'), C5'(H5'), C1A'(H1A'), C3A'(H3A'), C5A'(H5A')
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C4'(H4'a,H4'b), C7'(H7'a,H7'b), C16A(H16c,H16d), C4A'(H4Aa,
 H4Ab), C7A'(H7Aa,H7Ab)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C8A(H8A),
 C9A(H9A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A)
2.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C8'(H8'a,H8'b,H8'c), C9'(H9'a,H9'b,
 H9'c), C10'(H10a,H10b,H10c), C19(H19a,H19b,H19c), C17A(H17d,H17e,H17f),
 C18A(H18d,H18e,H18f), C8A'(H8Aa,H8Ab,H8Ac), C9A'(H9Aa,H9Ab,H9Ac)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3A)
;
_olex2_date_sample_data_collection 2017-11-27
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.232
_oxdiff_exptl_absorpt_empirical_full_min 0.451