Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508
Xu, Jianlin; Tan, Haibo; Chen, Yuchan; Li, Saini; Huang, Zilei; Guo, Heng; Li, Haohua; Gao, Xiaoxia; Liu, Hongxin; Zhang, Weimin; Organic Chemistry Frontiers 5 (2018) 1792–; doi:10.1039/C8QO00095F

data_1554257
_publ_section_title
;
 Lithocarpins A--D: four tenellone-macrolide conjugated [4 + 2]
 hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus
 FS508
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1792
_journal_paper_doi               10.1039/C8QO00095F
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C H Cl3, C37 H42 O11'
_chemical_formula_sum            'C38 H43 Cl3 O11'
_chemical_formula_weight         782.07
_chemical_name_common            'Lithocarpin A'
_chemical_name_systematic        w-36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-20 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.378(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0999(3)
_cell_length_b                   8.9388(2)
_cell_length_c                   17.0397(4)
_cell_measurement_reflns_used    8832
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3420
_cell_measurement_theta_min      4.4480
_cell_volume                     1842.95(8)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -82.00  39.00   1.00    1.00    --  -40.98  19.00  30.00  121
  2  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 -60.00   74
  3  \w     17.00 115.00   1.00    1.00    --   40.98  37.00-150.00   98
  4  \w     79.00 178.00   1.00    4.51    --  107.58  30.00 -30.00   99
  5  \w     79.00 178.00   1.00    4.51    --  107.58  30.00 120.00   99
  6  \w     94.00 178.00   1.00    4.51    --  107.58 125.00 -90.00   84
  7  \w     97.00 178.00   1.00    4.51    --  107.58 119.00 140.00   81
  8  \w     34.00 122.00   1.00    4.51    --  107.58-125.00  90.00   88
  9  \w     35.00 137.00   1.00    4.51    --  107.58 -61.00  30.00  102
 10  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00   0.00   98
 11  \w    -31.00  69.00   1.00    1.00    --   40.98 -57.00  60.00  100
 12  \w     17.00 115.00   1.00    1.00    --   40.98  37.00 -60.00   98
 13  \w     31.00 140.00   1.00    4.51    --  107.58 -77.00-180.00  109
 14  \w     79.00 178.00   1.00    4.51    --  107.58  30.00-120.00   99
 15  \w     75.00 178.00   1.00    4.51    --  107.58  77.00 150.00  103
 16  \w     78.00 152.00   1.00    4.51    --  107.58  61.00   0.00   74
 17  \w     75.00 178.00   1.00    4.51    --  107.58  77.00  30.00  103
;
_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      0.1157509000
_diffrn_orient_matrix_UB_12      -0.0677329000
_diffrn_orient_matrix_UB_13      0.0130446000
_diffrn_orient_matrix_UB_21      0.0230470000
_diffrn_orient_matrix_UB_22      0.0126440000
_diffrn_orient_matrix_UB_23      -0.0885270000
_diffrn_orient_matrix_UB_31      0.0479837000
_diffrn_orient_matrix_UB_32      0.1579173000
_diffrn_orient_matrix_UB_33      0.0127077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17295
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.760
_diffrn_reflns_theta_min         3.653
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66252
_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            white
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             820
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.202
_refine_diff_density_min         -1.438
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details
;
 Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.087(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6703
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0906
_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^)+(0.1996P)^2^+2.7116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2611
_refine_ls_wR_factor_ref         0.2650
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.836
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                6398
_reflns_number_total             6703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00095f2.cif
_cod_data_source_block           w-36
_cod_database_code               1554257
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.750
_shelx_estimated_absorpt_t_min   0.682
_reflns_odcompleteness_completeness 99.97
_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:
 C8"(H8"), C5"(H5"), C13"(H13"), C9'(H9'), C6"(H6"), C4"(H4"), C3"(H3"),
 C10"(H10"), C1S(H1S)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9"(H9"A,H9"B), C8'(H8'A,H8'B)
2.c Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C4(H4A), C5(H5), C4'(H4'), C8(H8)
2.d Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C12'(H12A,H12B,H12C), C15"(H15A,H15B,H15C), C11'(H11A,
 H11B,H11C), C11"(H11D,H11E,H11F), C11(H11G,H11H,H11I), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.519