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_1557884
_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 H17 Cl O7, C H4 O'
_chemical_formula_sum            'C19 H21 Cl O8'
_chemical_formula_weight         412.81
_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             2019-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8990(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.53453(7)
_cell_length_b                   5.13144(4)
_cell_length_c                   18.92992(13)
_cell_measurement_reflns_used    15251
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7350
_cell_measurement_theta_min      4.6550
_cell_volume                     921.258(12)
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -13.00  17.00   0.50    0.50    --    0.00 -38.00-150.00   60
  2  \w    -12.00  13.00   0.50    0.50    --    0.00  57.00 150.00   50
  3  \w     -2.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00   66
  4  \w    -82.00 -24.00   0.50    0.50    --    0.00 -38.00-150.00  116
  5  \w    -28.00  -3.00   0.50    0.50    --    0.00 -82.00 -60.00   50
  6  \w    -89.00 -32.00   0.50    0.50    --    0.00 -57.00 -60.00  114
  7  \w    -22.00  16.00   0.50    0.50    --    0.00 -19.00   0.00   76
  8  \w    -66.00 -33.00   0.50    0.50    --    0.00 -19.00   0.00   66
  9  \w     -3.00  22.00   0.50    0.50    --    0.00 -57.00 -60.00   50
 10  \w    -17.00  88.00   0.50    0.50    --    0.00  38.00  60.00  210
 11  \w     21.00  81.00   0.50    0.50    --    0.00  57.00 150.00  120
 12  \w    127.00 181.00   0.50    0.50    --   94.60  67.00 -51.18  108
 13  \w     73.00 105.00   0.50    0.50    --   94.60  52.00  71.38   64
 14  \w     72.00 102.00   0.50    0.50    --   94.60  57.00 -68.37   60
 15  \w     69.00  95.00   0.50    0.50    --   94.60  67.00 -51.18   52
 16  \w    154.00 180.00   0.50    0.50    --   94.60  63.00  73.36   52
 17  \w    140.00 179.00   0.50    0.50    --   94.60  52.00 -26.42   78
 18  \w     71.00  96.00   0.50    0.50    --   94.60  59.00  23.11   50
 19  \w    159.00 184.00   0.50    0.50    --   94.60  66.00 -24.05   50
 20  \w     71.00 102.00   0.50    0.50    --   94.60  63.00  73.36   62
 21  \w     69.00  94.00   0.50    0.50    --   94.60  66.00 -24.05   50
 22  \w     68.00 109.00   0.50    0.50    --   94.60  69.00 152.54   82
 23  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 -97.89   50
 24  \w    122.00 184.00   0.50    0.50    --   94.60  74.00 -97.89  124
 25  \w      5.00 118.00   0.50    0.50    --   94.60 -61.00-120.00  226
 26  \w      5.00 116.00   0.50    0.50    --   94.60 -82.00  60.00  222
 27  \w     72.00 153.00   0.50    0.50    --   94.60  56.00  76.56  162
 28  \w      6.00 116.00   0.50    0.50    --   94.60 -82.00-120.00  220
 29  \w     71.00 104.00   0.50    0.50    --   94.60  61.00-120.00   66
 30  \w     92.00 126.00   0.50    0.50    --   94.60 -82.00  90.00   68
 31  \w    115.00 141.00   0.50    0.50    --   94.60  65.00 145.25   52
 32  \w     77.00 129.00   0.50    0.50    --   94.60  52.00 -26.42  104
 33  \w    138.00 164.00   0.50    0.50    --   94.60  54.00-132.35   52
 34  \w     93.00 119.00   0.50    0.50    --   94.60 -82.00 120.00   52
 35  \w     26.00  74.00   0.50    0.50    --   94.60 -82.00 120.00   96
 36  \w     76.00 108.00   0.50    0.50    --   94.60  54.00-132.35   64
 37  \w     76.00 102.00   0.50    0.50    --   94.60  45.00 -90.00   52
 38  \w     75.00 108.00   0.50    0.50    --   94.60  48.00  10.77   66
 39  \w     70.00 103.00   0.50    0.50    --   94.60  65.00 145.25   66
 40  \w     51.00 125.00   0.50    0.50    --   94.60 -82.00 -30.00  148
 41  \w     71.00 100.00   0.50    0.50    --   94.60  61.00 -60.00   58
 42  \w     71.00 123.00   0.50    0.50    --   94.60  61.00  30.00  104
 43  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 120.00   52
 44  \w     81.00 132.00   0.50    0.50    --   94.60  30.00 -60.00  102
 45  \w    154.00 180.00   0.50    0.50    --   94.60  70.00 123.79   52
 46  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-150.00   50
 47  \w     77.00 134.00   0.50    0.50    --   94.60  45.00-150.00  114
 48  \w    149.00 175.00   0.50    0.50    --   94.60  45.00-150.00   52
 49  \w     71.00 168.00   0.50    0.50    --   94.60  61.00  90.00  194
 50  \w     68.00  94.00   0.50    0.50    --   94.60  70.00 123.79   52
 51  \w     73.00 183.00   0.50    0.50    --   94.60  54.00 122.27  220
 52  \w     63.00 100.00   0.50    0.50    --   94.60 -61.00 -30.00   74
 53  \w     72.00  98.00   0.50    0.50    --   94.60  58.00  50.03   52
 54  \w    121.00 146.00   0.50    0.50    --   94.60  57.00-176.60   50
 55  \w     72.00  98.00   0.50    0.50    --   94.60  57.00-176.60   52
;
_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      -0.1223672000
_diffrn_orient_matrix_UB_12      -0.1151774000
_diffrn_orient_matrix_UB_13      0.0370234000
_diffrn_orient_matrix_UB_21      -0.0465388000
_diffrn_orient_matrix_UB_22      -0.1616733000
_diffrn_orient_matrix_UB_23      -0.0669240000
_diffrn_orient_matrix_UB_31      0.0961535000
_diffrn_orient_matrix_UB_32      -0.2253363000
_diffrn_orient_matrix_UB_33      0.0290123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.947
_diffrn_reflns_theta_min         2.346
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53526
_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    1.488
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3676
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0233
_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^)+(0.0391P)^2^+0.2455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3653
_reflns_number_total             3676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01167_si_005.cif
_cod_data_source_block           20190628_zbf-6
_cod_original_cell_volume        921.258(11)
_cod_database_code               1557884
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.551
_reflns_odcompleteness_completeness 100.00
_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), C4(H4), C5(H5), C6(H6A), C7(H7A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O7(H7), O8(H8A)
;
_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 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.448