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_7230017
_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 unk
_chemical_formula_moiety         'C14 H15 Cl O5, 0.5(H2 O)'
_chemical_formula_sum            'C14 H16 Cl O5.5'
_chemical_formula_weight         307.72
_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   mixed
_audit_block_doi                 10.5517/cc1khzgh
_audit_creation_date             2016-01-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_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                   7.7241(4)
_cell_length_b                   16.3543(7)
_cell_length_c                   22.3393(9)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.099
_cell_measurement_theta_min      3.056
_cell_volume                     2822.0(2)
_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      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            43557
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         3.006
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8910.
The \l/2 correction factor is 0.0015.
;
_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    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1601 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   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         6467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0530P)^2^+0.8770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4597
_reflns_number_total             6467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra13327h2.cif
_cod_data_source_block           151229shaost5a_0m
_cod_original_formula_sum        'C14 H16 Cl O5.50'
_cod_database_code               7230017
_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, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Ternary CH refined with riding coordinates:
 C24(H24), C8(H8), C10(H10), C22(H22)
2.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4A), C20(H20), C6(H6), C18(H18), C17(H17), C3(H3A)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C1(H1A,H1B,H1C)
2.f Idealised tetrahedral OH refined as rotating group:
 O8(H8A), O3(H3), O9(H9)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'