Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum
Wang, Chao-Yi; Hao, Jun-Di; Ning, Xing-Yan; Wu, Jing-Shuai; Zhao, Dong-Lin; Kong, Chui-Jian; Shao, Chang-Lun; Wang, Chang-Yun; RSC Advances 8 (2018) 4348–; doi:10.1039/C7RA13327H

data_7230016
_publ_section_title
;
 Penicilazaphilones D and E: two new azaphilones from a sponge-derived
 strain of the fungus Penicillium sclerotiorum
;
_journal_issue                   8
_journal_name_full               'RSC Advances'
_journal_page_first              4348
_journal_paper_doi               10.1039/C7RA13327H
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration rmsd
_chemical_formula_moiety         'C19 H27 Cl O6'
_chemical_formula_sum            'C19 H27 Cl O6'
_chemical_formula_weight         386.85
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/cc1khz9b
_audit_creation_date             2016-01-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-05 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.446(3)
_cell_length_b                   15.594(3)
_cell_length_c                   25.490(5)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.220
_cell_measurement_theta_min      3.063
_cell_volume                     4947.2(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            74699
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         3.063
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1082 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.8775.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.039
_exptl_crystal_description       'the single crystal is block'
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         11415
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0566
_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^)+(0.1007P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5194
_reflns_number_total             11415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra13327h2.cif
_cod_data_source_block           1
_cod_original_cell_volume        4947.0(17)
_cod_database_code               7230016
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.948
_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
 C01D, C01F
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C01D \\sim C01F: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00L(H00L), C00W(H00W), C00Y(H00Y), C00Z(H00Z),
 C015(H015), C01D(H01T)
4.b Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C012(H01A,H01B), C017(H01O,H01P), C01H(H01Z,HA)
4.c Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P), C00V(H00V), C011(H011)
4.d Idealised Me refined as rotating group:
 C016(H01C,H01D,H01E), C018(H01F,H01G,H01H), C019(H01Q,H01R,H01S), C01A(H01I,
 H01J,H01K), C01B(H01L,H01M,H01N), C01E(H01U,H01V,H01W), C01F(H01X,H01Y,H),
 C01K(H01,HB,HC)
4.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005), O006(H006), O007(H007), O008(H008), O009(H009),
 O00A(H00C), O00D(H00D)
;
_shelx_res_checksum              26039
_olex2_submission_special_instructions 'No special instructions were received'