Resorcylic Acid Lactones from an Ilyonectria sp.
Zhou, Jia; Gao, Ying; Chang, Jin-Ling; Yu, Heng-Yi; Chen, Juan; Zhou, Ming; Meng, Xiang-Gao; Ruan, Han-Li; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b01167

data_1557893
_publ_section_title
;
 Resorcylic Acid Lactones from an Ilyonectria sp.
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01167
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 O6, C H4 O'
_chemical_formula_sum            'C19 H24 O7'
_chemical_formula_weight         364.38
_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     direct
_audit_creation_date             2019-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.53373(7)
_cell_length_b                   14.7351(2)
_cell_length_c                   23.2466(4)
_cell_measurement_reflns_used    8185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7580
_cell_measurement_theta_min      3.5530
_cell_volume                     1895.53(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -33.00  30.00   0.50    1.00    --    0.00 -82.00 -30.00  126
  2  \w    -16.00   9.00   0.50    1.00    --    0.00 -82.00 -90.00   50
  3  \w    -25.00  15.00   0.50    1.00    --    0.00 -82.00  30.00   80
  4  \w    -32.00  28.00   0.50    1.00    --    0.00 -82.00-180.00  120
  5  \w    -22.00  47.00   0.50    1.00    --    0.00  57.00 150.00  138
  6  \w    -30.00   4.00   0.50    1.00    --    0.00 -82.00 120.00   68
  7  \w     11.00  37.00   0.50    3.00    --   94.60 -82.00-150.00   52
  8  \w      5.00  92.00   0.50    3.00    --   94.60 -45.00 150.00  174
  9  \w     88.00 120.00   0.50    3.00    --   94.60  82.00  90.00   64
 10  \w    150.00 176.00   0.50    3.00    --   94.60  77.00 -60.00   52
 11  \w     46.00 101.00   0.50    3.00    --   94.60 -82.00  90.00  110
 12  \w     11.00 110.00   0.50    3.00    --   94.60 -30.00-180.00  198
 13  \w     92.00 137.00   0.50    3.00    --   94.60  77.00 -60.00   90
 14  \w     60.00 126.00   0.50    3.00    --   94.60 -82.00-150.00  132
 15  \w     61.00 126.00   0.50    3.00    --   94.60 -82.00 -60.00  130
 16  \w     86.00 125.00   0.50    3.00    --   94.60 -82.00 150.00   78
 17  \w     14.00 126.00   0.50    3.00    --   94.60 -82.00   0.00  224
 18  \w     82.00 108.00   0.50    3.00    --   94.60 -61.00   0.00   52
 19  \w     72.00 178.00   0.50    3.00    --   94.60  15.00 120.00  212
 20  \w     30.00  74.00   0.50    3.00    --   94.60 -61.00   0.00   88
 21  \w    151.00 184.00   0.50    3.00    --   94.60  82.00  90.00   66
 22  \w     26.00  81.00   0.50    3.00    --   94.60 -77.00 150.00  110
 23  \w     74.00  99.00   0.50    3.00    --   94.60 -82.00  60.00   50
 24  \w     17.00 101.00   0.50    3.00    --   94.60 -30.00 -30.00  168
;
_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      -0.0197570000
_diffrn_orient_matrix_UB_12      0.0171382000
_diffrn_orient_matrix_UB_13      0.0651973000
_diffrn_orient_matrix_UB_21      -0.0307526000
_diffrn_orient_matrix_UB_22      0.1023792000
_diffrn_orient_matrix_UB_23      -0.0113125000
_diffrn_orient_matrix_UB_31      -0.2759855000
_diffrn_orient_matrix_UB_32      -0.0126126000
_diffrn_orient_matrix_UB_33      -0.0034223000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19162
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.919
_diffrn_reflns_theta_min         3.551
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0458P)^2^+0.1265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3269
_reflns_number_total             3767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01167_si_011.cif
_cod_data_source_block           20190920_zbf-56
_cod_original_cell_volume        1895.52(5)
_cod_database_code               1557893
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.687
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5A), C13(H13), C15(H15)
2.d Tetrahedral OH refined with riding coordinates:
 O7(H7)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6)
;
_shelx_res_checksum              52904
_shelx_hkl_checksum              54673
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.570