Paecilosetin Derivatives as Potent Antimicrobial Agents from <i>Isaria farinosa</i>.
Brel, Orianne; Touré, Seindé; Levasseur, Marceau; Lechat, Christian; Pellissier, Léonie; Wolfender, Jean-Luc; Van-Elslande, Elsa; Litaudon, Marc; Dusfour, Isabelle; Stien, Didier; Eparvier, Véronique; Journal of natural products 83 (2020) 2915–2922; doi:10.1021/acs.jnatprod.0c00444

data_1559278
_publ_section_title
;
 Paecilosetin Derivatives as Potent Antimicrobial Agents from <i>Isaria
 farinosa</i>.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2915
_journal_page_last               2922
_journal_paper_doi               10.1021/acs.jnatprod.0c00444
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'Isaria farinosa'
_chemical_formula_moiety         'C22 H29 N O3'
_chemical_formula_sum            'C22 H29 N O3'
_chemical_formula_weight         355.46
_chemical_name_common            'Paecilosetin C'
_chemical_name_systematic        'Compound 5'
_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             2020-02-19
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5830(5)
_cell_length_b                   15.4136(5)
_cell_length_c                   19.6284(14)
_cell_measurement_reflns_used    10129
_cell_measurement_temperature    235
_cell_measurement_theta_max      69.7
_cell_measurement_theta_min      6.5
_cell_volume                     4109.5(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 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    'SHELXT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      235.15
_diffrn_detector                 'Rapid 2'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device
'four-circle partial \c goniometer diffractometer'
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Confocal Osmic mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21525
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         70.012
_diffrn_reflns_theta_min         6.518
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku micromax 007 1.2kW'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku, 1998)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       needles
_exptl_crystal_F_000             1536
_exptl_crystal_preparation       Methanol
_exptl_crystal_recrystallization_method 'MeOH solution evaporation at 5\%C'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         7402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0382P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                3450
_reflns_number_total             7402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00444_si_002.cif
_cod_data_source_block           compound5
_cod_depositor_comments          'Adding full bibliography for 1559278.cif.'
_cod_database_code               1559278
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.817
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C11B(H11B), C11A(H11A), C6B(H6B), C8B(H8B), C8A(H8A), C3B(H3B), C3A(H3A),
 C6A(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C10B(H10A,H10B), C9B(H9BA,H9BB), C10A(H10C,H10D), C7B(H7BA,H7BB), C9A(H9AA,
 H9AB), C7A(H7AA,H7AB)
2.c Aromatic/amide H refined with riding coordinates:
 C6'B(H6'B), C6'A(H6'A), C5B(H5B), C13B(H13B), C4B(H4B), C13A(H13A),
 C14B(H14B), C14A(H14A), C4A(H4A), C5A(H5A)
2.d Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C7'A(H7'D,H7'E,H7'F), C7'B(H7'A,H7'B,H7'C), C12A(H12D,
 H12E,H12F), C15B(H15A,H15B,H15C), C16B(H16A,H16B,H16C), C16A(H16D,H16E,H16F),
 C15A(H15D,H15E,H15F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2B'(H2B'), O2A'(H2A')
;
_shelx_res_checksum              98938
_shelx_hkl_checksum              70069
_olex2_submission_special_instructions 'No special instructions were received'