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_1557888
_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         'C16 H17 Cl O5, H2 O'
_chemical_formula_sum            'C16 H19 Cl O6'
_chemical_formula_weight         342.76
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2019-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                69.576(3)
_cell_angle_beta                 84.021(3)
_cell_angle_gamma                68.822(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6811(3)
_cell_length_b                   9.5462(2)
_cell_length_c                   10.9510(4)
_cell_measurement_reflns_used    13149
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6490
_cell_measurement_theta_min      4.3200
_cell_volume                     792.79(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    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_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    -39.00  16.00   0.50    0.50    --    0.00 -38.00 -30.00  110
  2  \w     40.00  80.00   0.50    0.50    --    0.00  38.00 150.00   80
  3  \w    -17.00  15.00   0.50    0.50    --    0.00  38.00 -30.00   64
  4  \w     47.00  76.00   0.50    0.50    --    0.00  38.00  60.00   58
  5  \w     32.00  85.00   0.50    0.50    --    0.00  57.00-120.00  106
  6  \w    -29.00  -3.00   0.50    0.50    --    0.00 -82.00  60.00   52
  7  \w    -17.00  35.00   0.50    0.50    --    0.00  38.00 150.00  104
  8  \w     57.00  86.00   0.50    0.50    --    0.00  38.00 -30.00   58
  9  \w    -11.00  38.00   0.50    0.50    --    0.00  38.00  60.00   98
 10  \w    -28.00  31.00   0.50    0.50    --    0.00 -82.00  90.00  118
 11  \w    -69.00 -43.00   0.50    0.50    --    0.00 -38.00 -30.00   52
 12  \w    -21.00  20.00   0.50    0.50    --    0.00  57.00-120.00   82
 13  \w     69.00  95.00   0.50    0.50    --   94.60  74.00 -94.81   52
 14  \w    147.00 183.00   0.50    0.50    --   94.60  59.00 136.38   72
 15  \w     69.00  95.00   0.50    0.50    --   94.60  67.00-131.19   52
 16  \w     71.00 144.00   0.50    0.50    --   94.60  59.00 136.38  146
 17  \w    146.00 175.00   0.50    0.50    --   94.60  69.00-160.23   58
 18  \w     72.00  98.00   0.50    0.50    --   94.60  58.00  88.70   52
 19  \w     66.00  97.00   0.50    0.50    --   94.60  75.00   4.15   62
 20  \w     83.00 122.00   0.50    0.50    --   94.60 -82.00 -60.00   78
 21  \w     68.00  95.00   0.50    0.50    --   94.60  69.00-160.23   54
 22  \w      8.00  71.00   0.50    0.50    --   94.60 -82.00 -60.00  126
 23  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 120.00   50
 24  \w     51.00 126.00   0.50    0.50    --   94.60 -82.00-150.00  150
 25  \w     94.00 122.00   0.50    0.50    --   94.60 -77.00  30.00   56
 26  \w     67.00  92.00   0.50    0.50    --   94.60  73.00-106.25   50
 27  \w     71.00 125.00   0.50    0.50    --   94.60  61.00 -30.00  108
 28  \w    136.00 183.00   0.50    0.50    --   94.60  61.00 -30.00   94
 29  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 150.00   52
 30  \w     76.00 105.00   0.50    0.50    --   94.60  45.00  60.00   58
 31  \w     73.00 132.00   0.50    0.50    --   94.60  61.00   0.00  118
 32  \w     71.00 106.00   0.50    0.50    --   94.60  60.00 -46.66   70
 33  \w     72.00  97.00   0.50    0.50    --   94.60  56.00  61.38   50
 34  \w     78.00 146.00   0.50    0.50    --   94.60  45.00  90.00  136
 35  \w    139.00 167.00   0.50    0.50    --   94.60  53.00  24.08   56
 36  \w    124.00 149.00   0.50    0.50    --   94.60  75.00 -24.57   50
 37  \w     75.00 144.00   0.50    0.50    --   94.60  45.00 -90.00  138
 38  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-180.00   50
 39  \w     77.00 162.00   0.50    0.50    --   94.60  45.00 120.00  170
 40  \w    138.00 164.00   0.50    0.50    --   94.60  61.00   0.00   52
 41  \w     80.00 184.00   0.50    0.50    --   94.60  45.00-120.00  208
 42  \w     73.00  99.00   0.50    0.50    --   94.60  53.00  24.08   52
 43  \w     83.00 123.00   0.50    0.50    --   94.60 -82.00 -90.00   80
 44  \w     74.00 100.00   0.50    0.50    --   94.60  61.00  60.00   52
 45  \w     12.00  75.00   0.50    0.50    --   94.60 -82.00 -90.00  126
 46  \w    124.00 184.00   0.50    0.50    --   94.60  74.00 -94.81  120
 47  \w     78.00 182.00   0.50    0.50    --   94.60  45.00-150.00  208
 48  \w     14.00 120.00   0.50    0.50    --   94.60 -82.00   0.00  212
 49  \w     66.00  91.00   0.50    0.50    --   94.60  75.00 -24.57   50
 50  \w    122.00 182.00   0.50    0.50    --   94.60  75.00   4.15  120
 51  \w    137.00 184.00   0.50    0.50    --   94.60  71.00 -79.02   94
 52  \w     75.00 101.00   0.50    0.50    --   94.60  45.00-180.00   52
 53  \w    156.00 181.00   0.50    0.50    --   94.60  45.00-180.00   50
 54  \w     41.00  67.00   0.50    0.50    --   94.60 -82.00  90.00   52
 55  \w     87.00 119.00   0.50    0.50    --   94.60 -82.00  90.00   64
 56  \w     67.00  95.00   0.50    0.50    --   94.60  71.00 -79.02   56
;
_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      0.1531080000
_diffrn_orient_matrix_UB_12      0.0506278000
_diffrn_orient_matrix_UB_13      -0.0333039000
_diffrn_orient_matrix_UB_21      -0.0014683000
_diffrn_orient_matrix_UB_22      -0.0085435000
_diffrn_orient_matrix_UB_23      -0.1377594000
_diffrn_orient_matrix_UB_31      -0.1131317000
_diffrn_orient_matrix_UB_32      0.1764108000
_diffrn_orient_matrix_UB_33      -0.0496150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14972
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.043
_diffrn_reflns_theta_min         4.309
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43602
_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    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         5745
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0424P)^2^+0.1528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                5701
_reflns_number_total             5745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01167_si_012.cif
_cod_data_source_block           20190628_zbf-133
_cod_original_cell_volume        792.78(5)
_cod_database_code               1557888
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.585
_reflns_odcompleteness_completeness 99.72
_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, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C2A(H2AA), C3A(H3AA)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C6A(H6AA,H6AB), C7A(H7AA,H7AB)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C13(H13), C4A(H4A), C5A(H5A), C8A(H8A),
 C9A(H9A), C13A(H13A)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A), O3(H3A), O1A(H1AD), O2A(H2AB), O3A(H3AB)
;
_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 2.056
_oxdiff_exptl_absorpt_empirical_full_min 0.757