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_1557892
_publ_section_title
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 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 H22 O6, 2(H2 O)'
_chemical_formula_sum            'C18 H26 O8'
_chemical_formula_weight         370.39
_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   mixed
_audit_creation_date             2018-11-16
_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                   8.4937(2)
_cell_length_b                   13.9436(3)
_cell_length_c                   16.0615(3)
_cell_measurement_reflns_used    5157
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.83
_cell_measurement_theta_min      8.23
_cell_volume                     1902.21(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297.15
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12105
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        64.975
_diffrn_reflns_theta_max         64.975
_diffrn_reflns_theta_min         7.591
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1637 before and 0.0370 after correction. 
The Ratio of minimum to maximum transmission is 0.8346. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
; 
 Flack x determined using 1188 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0654P)^2^+0.0547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2922
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01167_si_006.cif
_cod_data_source_block           cu_181115b_0m
_cod_database_code               1557892
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.904
_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. Restrained distances 
 O7-H7D = O7-H7C 
 0.82 with sigma of 0.01 
 O8-H8C = O8-H8D 
 0.82 with sigma of 0.01 
 H7D-H7C = H8C-H8D 
 1.35 with sigma of 0.02 
3.a Ternary CH refined with riding coordinates: 
 C2(H2), C3(H3) 
3.b Secondary CH2 refined with riding coordinates: 
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B) 
3.c Aromatic/amide H refined with riding coordinates: 
 C4(H4), C5(H5), C13(H13), C15(H15) 
3.d Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C) 
3.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3A), O5(H5A), O6(H6) 
;
_olex2_submission_special_instructions 'No special instructions were received'