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_1557890
_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         'C20 H23 Cl O6'
_chemical_formula_sum            'C20 H23 Cl O6'
_chemical_formula_weight         394.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_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                 131.699(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   36.0878(7)
_cell_length_b                   10.82580(10)
_cell_length_c                   26.8601(9)
_cell_measurement_reflns_used    19738
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      4.393
_cell_measurement_theta_min      73.380
_cell_volume                     7835.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            44030
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.929
_diffrn_reflns_theta_min         3.280
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.017
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 3903 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.015(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1018
_refine_ls_number_reflns         13690
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0856P)^2^+2.3362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.758
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                11563
_reflns_number_total             13690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01167_si_004.cif
_cod_data_source_block           t
_cod_original_cell_volume        7835.1(4)
_cod_database_code               1557890
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.752
_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. Restrained distances 
 C2C-C1C 
 1.51 with sigma of 0.01 
 C4C-C3C = C4C-C3D = C3D-C2D = C3C-C2C = C2D-C1D = C2C-C1C 
 1.51 with sigma of 0.01 
 O2C-C2D = O2C-C2C 
 1.42 with sigma of 0.01 
 C1C-C2C \\sim C1D-C2D 
 with sigma of 0.02 
 C2C-C3C \\sim C2D-C3D 
 with sigma of 0.02 
 C2C-O2C \\sim C2D-O2C 
 with sigma of 0.02 
 C3C-C4C \\sim C3D-C4C 
 with sigma of 0.02 
 C1C-C3C \\sim C1D-C3D 
 with sigma of 0.04 
 C1C-O2C \\sim C1D-O2C 
 with sigma of 0.04 
 C2C-C4C \\sim C2D-C4C 
 with sigma of 0.04 
 C3C-O2C \\sim C3D-O2C 
 with sigma of 0.04 
3. Uiso/Uaniso restraints and constraints 
Uanis(O1C) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim 
Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for 
terminal atoms of 0.02 
4. Others 
 Sof(H4CA)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(C2D)=Sof(H2D)=Sof(C3D)= 
 Sof(H3DA)=Sof(H3DB)=1-FVAR(1) 
 Sof(H4C)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(C2C)=Sof(H2C)=Sof(C3C)= 
 Sof(H3CA)=Sof(H3CB)=FVAR(1) 
5.a Ternary CH refined with riding coordinates: 
 C2(H2), C10(H10), C2A(H2A), C10A(H10A), C2B(H2B), C10B(H10B), C10C(H10C), 
 C2C(H2C), C2D(H2D) 
5.b Secondary CH2 refined with riding coordinates: 
 C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11C,H11D), C13(H13C,H13D), 
 C3A(H3AA,H3AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C11A(H11E,H11F), C13A(H13E, 
 H13F), C3B(H3BA,H3BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C11B(H11G,H11H), 
 C13B(H13G,H13H), C6C(H6CA,H6CB), C7C(H7CA,H7CB), C11C(H11A,H11B), C13C(H13A, 
 H13B), C3C(H3CA,H3CB), C3D(H3DA,H3DB) 
5.c Aromatic/amide H refined with riding coordinates: 
 C4(H4), C5(H5), C8(H8), C9(H9), C17(H17), C4A(H4A), C5A(H5AA), C8A(H8A), 
 C9A(H9A), C17A(H17A), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C17B(H17B), 
 C4C(H4C), C4C(H4CA), C5C(H5C), C8C(H8C), C9C(H9C), C17C(H17C) 
5.d Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB, 
 H1CC), C1D(H1DA,H1DB,H1DC) 
5.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3), O5(H5A), O6(H6), O3A(H3AC), O5A(H5AB), O6A(H6AC), O3B(H3BC), 
 O5B(H5BA), O6B(H6BC), O3C(H3C), O5C(H5CA), O6C(H6C) 
;
_shelx_res_checksum              6606
_shelx_hkl_checksum              40210
_olex2_submission_special_instructions 'No special instructions were received'