Azaphilone Alkaloids with Anti-inflammatory Activity from Fungus Penicillium sclerotiorum cib-411.
Tang, Jia-Lin; Zhou, Zong-Yuan; Yang, Tao; Yao, Can; Wu, Lin-Wei; Li, Guo-You; Journal of agricultural and food chemistry 67 (2019) 2175–2182; doi:10.1021/acs.jafc.8b05628

data_1552553
_publ_section_title
;
 Azaphilone Alkaloids with Anti-inflammatory Activity from Fungus
 Penicillium sclerotiorum cib-411.
;
_journal_issue                   8
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              2175
_journal_page_last               2182
_journal_paper_doi               10.1021/acs.jafc.8b05628
_journal_volume                  67
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H27 Cl N O5'
_chemical_formula_sum            'C23 H27 Cl N O5'
_chemical_formula_weight         432.90
_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     direct
_audit_creation_date             2018-12-10
_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                   6.4844(6)
_cell_length_b                   8.7749(8)
_cell_length_c                   39.690(4)
_cell_measurement_reflns_used    8042
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.79
_cell_volume                     2258.4(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            20270
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.538
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2484
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.771
_refine_diff_density_min         -1.490
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 1189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     199
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1569
_refine_ls_R_factor_gt           0.1441
_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^)+(0.1759P)^2^+16.7984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3532
_refine_ls_wR_factor_ref         0.3645
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                3910
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf8b05628_si_003.cif
_cod_data_source_block           mo_luodaibin_20181207_1_0m_a
_cod_database_code               1552553
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.933
_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. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.001
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(H2AA)=Sof(O5A)=Sof(H5A)=1-FVAR(1)
 Sof(H2A)=Sof(O5)=Sof(H5)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2A(H2A), C2A(H2AA), C4(H4), C9(H9), C10(H10), C12(H12)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C)
5.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5A(H5A)
;
_shelx_res_checksum              75685
_shelx_hkl_checksum              42091
_olex2_submission_special_instructions 'No special instructions were received'