Cytorhizophins A and B, benzophenone-hemiterpene adducts from the endophytic fungus Cytospora rhizophorae
Liu, Hongxin; Tan, Haibo; Wang, Wenxuan; Zhang, Wenge; Chen, Yuchan; Li, Saini; Liu, Zhaoming; Li, Haohua; Zhang, Weimin; Organic Chemistry Frontiers 6 (2019) 591–; doi:10.1039/C8QO01306C

data_1554567
_publ_section_title
;
 Cytorhizophins A and B, benzophenone-hemiterpene adducts from the
 endophytic fungus Cytospora rhizophorae
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              591
_journal_paper_doi               10.1039/C8QO01306C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C22 H24 O7'
_chemical_formula_sum            'C22 H24 O7'
_chemical_formula_weight         400.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-19 deposited with the CCDC.
2019-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                95.1870(10)
_cell_angle_beta                 95.2940(10)
_cell_angle_gamma                103.0400(10)
_cell_formula_units_Z            4
_cell_length_a                   9.13750(10)
_cell_length_b                   13.1527(2)
_cell_length_c                   16.3540(3)
_cell_measurement_reflns_used    14738
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      73.7050
_cell_measurement_theta_min      5.3880
_cell_volume                     1894.04(5)
_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      100.00(18)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.962
_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    -23.00  28.00   0.50    0.50    --    0.00 -77.00  60.00  102
  2  \w    -32.00  31.00   0.50    0.50    --    0.00 -82.00-150.00  126
  3  \w     -6.00  51.00   0.50    0.50    --    0.00  38.00  60.00  114
  4  \w    -30.00  30.00   0.50    0.50    --    0.00 -82.00   0.00  120
  5  \w    -30.00  17.00   0.50    0.50    --    0.00 -82.00 -60.00   94
  6  \w     -4.00  27.00   0.50    0.50    --    0.00 -82.00-120.00   62
  7  \w      7.00  44.00   0.50    0.81    --   95.20 -30.00  90.00   74
  8  \w      7.00 112.00   0.50    0.81    --   95.20 -30.00-180.00  210
  9  \w     27.00 116.00   0.50    0.81    --   95.20 -82.00   0.00  178
 10  \w     77.00 104.00   0.50    0.81    --   95.20 -82.00-120.00   54
 11  \w     37.00 109.00   0.50    0.81    --   95.20 -61.00-120.00  144
 12  \w     42.00 126.00   0.50    0.81    --   95.20 -82.00 120.00  168
 13  \w     10.00  35.00   0.50    0.81    --   95.20 -61.00  90.00   50
 14  \w     22.00  49.00   0.50    0.81    --   95.20 -82.00-120.00   54
 15  \w     82.00 107.00   0.50    0.81    --   95.20 -82.00-180.00   50
 16  \w      7.00  33.00   0.50    0.81    --   95.20 -82.00 -90.00   52
 17  \w     32.00 116.00   0.50    0.81    --   95.20 -61.00 120.00  168
 18  \w     29.00 115.00   0.50    0.81    --   95.20 -61.00   0.00  172
 19  \w     65.00 111.00   0.50    0.81    --   95.20 -82.00 -90.00   92
 20  \w     86.00 111.00   0.50    0.81    --   95.20 -82.00  30.00   50
 21  \w    117.00 142.00   0.50    0.81    --   95.20  30.00-120.00   50
 22  \w    159.00 185.00   0.50    0.81    --   95.20  30.00-120.00   52
 23  \w     23.00 104.00   0.50    0.81    --   95.20 -15.00 -90.00  162
 24  \w     23.00  49.00   0.50    0.81    --   95.20 -82.00-180.00   52
 25  \w     80.00 184.00   0.50    0.81    --   95.20   0.00-180.00  208
 26  \w      6.00  62.00   0.50    0.81    --   95.20   0.00-180.00  112
;
_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      0.0712575000
_diffrn_orient_matrix_UB_12      0.0165570000
_diffrn_orient_matrix_UB_13      -0.0809969000
_diffrn_orient_matrix_UB_21      0.1455146000
_diffrn_orient_matrix_UB_22      0.0692050000
_diffrn_orient_matrix_UB_23      0.0494802000
_diffrn_orient_matrix_UB_31      0.0640908000
_diffrn_orient_matrix_UB_32      -0.0978990000
_diffrn_orient_matrix_UB_33      0.0077791000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19534
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.142
_diffrn_reflns_theta_min         3.472
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85239
_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    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     540
_refine_ls_number_reflns         7411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0375
_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^+0.7972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6866
_reflns_number_total             7411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01306c2.cif
_cod_data_source_block           liuhogxin_a761-12b_collect
_cod_database_code               1554567
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C88 H94 O28 '
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.780
_reflns_odcompleteness_completeness 99.56
_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'), C1A'(H1A')
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15A(H15C,H15D), C2'(H2'A,H2'B), C2A'(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3A), C1(H1A), C2(H2), C1A(H1AA), C3A(H3AA), C12A(H12A), C2A(H2A)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C5'(H5'A,H5'B,H5'C), C4'(H4'A,H4'B,H4'C), C16A(H16D,H16E,
 H16F), C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F), C5A'(H5AA,H5AB,H5AC),
 C4A'(H4AA,H4AB,H4AC)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O3'(H3'), O1'(H1'A), O7'(H7')
;
_shelx_res_checksum              48374
_shelx_hkl_checksum              12573
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.744