Rhizophols A and B, antioxidant and axially chiral benzophenones from the endophytic fungus Cytospora rhizophorae
Liu, Zhaoming; Tan, Haibo; Chen, Kai; Chen, Yuchan; Zhang, Wenge; Chen, Shanchong; Liu, Hong-Xin; Zhang, Weimin; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02282A

data_7157197
_publ_section_title
;
 Rhizophols A and B, antioxidant and axially chiral benzophenones from the
 endophytic fungus Cytospora rhizophorae
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02282A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 O6'
_chemical_formula_sum            'C22 H22 O6'
_chemical_formula_weight         382.39
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8000(2)
_cell_length_b                   15.6030(4)
_cell_length_c                   17.7559(6)
_cell_measurement_reflns_used    3835
_cell_measurement_temperature    99.98(12)
_cell_measurement_theta_max      73.1880
_cell_measurement_theta_min      5.0070
_cell_volume                     1883.91(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (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      99.98(12)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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     -9.00  19.35   0.45    3.20    --    0.00 -82.00 -90.00   63
  2  \w    -33.00  28.20   0.45    3.20    --    0.00 -82.00-180.00  136
  3  \w    -31.00   0.05   0.45    3.20    --    0.00 -82.00 150.00   69
  4  \w    -33.00  24.15   0.45    3.20    --    0.00 -82.00-120.00  127
  5  \w     75.00 181.65   0.45   31.00    --   94.60  45.00 -60.00  237
  6  \w     10.00 107.20   0.45   31.00    --   94.60 -61.00-150.00  216
  7  \w     64.00 112.60   0.45   31.00    --   94.60 -61.00   0.00  108
  8  \w     79.00 171.70   0.45   31.00    --   94.60  30.00-150.00  206
  9  \w     34.00  63.25   0.45   31.00    --   94.60 -82.00-150.00   65
 10  \w     65.00 120.35   0.45   31.00    --   94.60 -82.00-150.00  123
 11  \w     11.00  46.10   0.45   31.00    --   94.60 -61.00   0.00   78
 12  \w    140.00 170.60   0.45   31.00    --   94.60  82.00 120.00   68
 13  \w     97.00 124.00   0.45   31.00    --   94.60  82.00 120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1399429000
_diffrn_orient_matrix_UB_12      0.0122509000
_diffrn_orient_matrix_UB_13      -0.0673308000
_diffrn_orient_matrix_UB_21      0.1772144000
_diffrn_orient_matrix_UB_22      0.0193610000
_diffrn_orient_matrix_UB_23      -0.0512932000
_diffrn_orient_matrix_UB_31      0.0178501000
_diffrn_orient_matrix_UB_32      -0.0960730000
_diffrn_orient_matrix_UB_33      -0.0190098000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9486
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.559
_diffrn_reflns_theta_min         3.771
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0640P)^2^+0.4100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                3238
_reflns_number_total             3675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02282a2.cif
_cod_data_source_block           liuhongxin_b3_collect
_cod_depositor_comments
;

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C88 H88 O24'
_cod_original_formula_weight         1529.58
_cod_original_formula_moiety         '4(C22 H22 O6)'
_cod_original_formula_units_Z            1
_cod_database_code               7157197
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C88 H76 O24 '
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.855
_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, 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:
 C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C17(H00A,H00B,H00C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C), C16(H16A,H16B,
 H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              10222
_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 1.924
_oxdiff_exptl_absorpt_empirical_full_min 0.455