Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus <i>Septoria rudbeckiae</i>.
Li-Bin, Lin; Xiao, Jian; Zhang, Qiang; Han, Rui; Xu, Biao; Yang, Sheng-Xiang; Han, Wen-Bo; Tang, Jiang-Jiang; Gao, Jin-Ming; Journal of agricultural and food chemistry 69 (2021) 11878–11889; doi:10.1021/acs.jafc.1c04131

data_1565108
_publ_section_title
;
 Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory
 Activities from the Endophytic Fungus <i>Septoria rudbeckiae</i>.
;
_journal_issue                   40
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              11878
_journal_page_last               11889
_journal_paper_doi               10.1021/acs.jafc.1c04131
_journal_volume                  69
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H22 O4'
_chemical_formula_sum            'C15 H22 O4'
_chemical_formula_weight         266.32
_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     iterative
_audit_creation_date             2019-04-03
_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                   9.2430(2)
_cell_length_b                   10.9509(3)
_cell_length_c                   13.4319(4)
_cell_measurement_reflns_used    6356
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.64
_cell_measurement_theta_min      5.21
_cell_volume                     1359.57(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10051
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         5.211
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1263 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.8435. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0311P)^2^+0.2401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2161
_reflns_number_total             2382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf1c04131_si_002.cif
_cod_data_source_block           cu_0403_11_0m
_cod_database_code               1565108
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.895
_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:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              17841
_shelx_hkl_checksum              34408
_olex2_submission_special_instructions 'No special instructions were received'