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_1552554
_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         'C21 H24 Cl N O4'
_chemical_formula_sum            'C21 H24 Cl N O4'
_chemical_formula_weight         389.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.700(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3616(5)
_cell_length_b                   8.6802(4)
_cell_length_c                   31.9635(16)
_cell_measurement_reflns_used    1718
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6050
_cell_measurement_theta_min      3.7980
_cell_volume                     2040.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -12.00   41.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   19.0000  -30.0000 53

  2 omega   23.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000   30.0000 61

  3 omega    1.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000 -180.0000 65

  4 omega  -19.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -150.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0921129000
_diffrn_orient_matrix_UB_12      0.0054570000
_diffrn_orient_matrix_UB_13      0.0073859000
_diffrn_orient_matrix_UB_21      -0.0276948000
_diffrn_orient_matrix_UB_22      -0.0007094000
_diffrn_orient_matrix_UB_23      0.0209487000
_diffrn_orient_matrix_UB_31      0.0064035000
_diffrn_orient_matrix_UB_32      -0.0815867000
_diffrn_orient_matrix_UB_33      0.0003280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            4568
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.028
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.2043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.408
_reflns_Friedel_fraction_full    0.502
_reflns_Friedel_fraction_max     0.468
_reflns_number_gt                2663
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf8b05628_si_002.cif
_cod_data_source_block           170427_s2_tjl
_cod_database_code               1552554
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.920
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C8(H8), C13(H13), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'