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_1554568
_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_absolute_configuration ad
_chemical_formula_moiety         'C H Cl3, C17 H16 O5'
_chemical_formula_sum            'C18 H17 Cl3 O5'
_chemical_formula_weight         419.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_Hall           'P 2y'
_space_group_name_H-M_alt        'P 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-11-20 deposited with the CCDC.
2019-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.204(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8718(6)
_cell_length_b                   9.6965(5)
_cell_length_c                   13.8978(7)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      73.1720
_cell_measurement_theta_min      5.5210
_cell_volume                     1867.98(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.41b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.41b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.41b (Rigaku OD, 2018)'
_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      99.9(3)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -30.00  12.00   0.30    4.00    --    0.00 -82.00-150.00  140
  2  \w     -4.00  88.10   0.30    4.00    --    0.00  38.00 -30.00  307
  3  \w    -23.00  14.80   0.30    4.00    --    0.00 -77.00 150.00  126
  4  \w     78.00 153.90   0.30   35.00    --   94.60  15.00-150.00  253
  5  \w     15.00  96.00   0.30   35.00    --   94.60 -15.00 -90.00  270
  6  \w     87.00 181.20   0.30   35.00    --   94.60  30.00-120.00  314
  7  \w    109.00 183.10   0.30   35.00    --   94.60  30.00 -90.00  247
  8  \w     54.00  79.80   0.30   35.00    --   94.60 -30.00 120.00   86
  9  \w      5.00  33.50   0.30   35.00    --   94.60 -30.00 120.00   95
 10  \w    132.00 183.00   0.30   35.00    --   94.60  82.00 150.00  170
 11  \w     30.00 110.10   0.30   35.00    --   94.60 -30.00  60.00  267
 12  \w     35.00 110.90   0.30   35.00    --   94.60 -61.00 -90.00  253
;
_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      -0.0555952000
_diffrn_orient_matrix_UB_12      -0.0785959000
_diffrn_orient_matrix_UB_13      0.0765932000
_diffrn_orient_matrix_UB_21      -0.0951060000
_diffrn_orient_matrix_UB_22      0.0649290000
_diffrn_orient_matrix_UB_23      -0.0389158000
_diffrn_orient_matrix_UB_31      -0.0147086000
_diffrn_orient_matrix_UB_32      -0.1218661000
_diffrn_orient_matrix_UB_33      -0.0701746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8789
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.419
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.41b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.166
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.007(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         8789
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1414P)^2^+2.3141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2154
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.839
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                7817
_reflns_number_total             8789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01306c2.cif
_cod_data_source_block           lihongxin_a761-37_collect_mmmt2_twin1_hklf4
_cod_database_code               1554568
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.454
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.650(2)
 0.350(2)
2. 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
3. Others
 Fixed Sof: C01H(0.5) H01L(0.5) C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5)
4.a Ternary CH refined with riding coordinates:
 C01H(H01L), C5(H5), C6(H6), C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C00P(H00J,H00K), C01F(H01E,H01F)
4.c Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00T(H00T), C00W(H00W), C00X(H00X), C012(H012), C013(H013),
 C017(H017), C01B(H01D), C01E(H01K), C01G(H01G)
4.d Idealised Me refined as rotating group:
 C00R(H00L,H00M,H00N), C00Y(H00A,H00C,H00D), C016(H01H,H01I,H01J), C018(H01A,
 H01B,H01C)
4.e Idealised tetrahedral OH refined as rotating group:
 O00B(H00B), O00C(H00F), O00E(H00E), O00G(H00G), O00H(H00H), O00I(H00I)
;
_shelx_res_checksum              78321
_shelx_hkl_checksum              41079
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.586
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by 87.9337\% 
 around [-0.00 -1.00 0.00] (reciprocal) or [0.00 -1.00 0.00] (direct)
;