Cytotoxic Nitrogenated Azaphilones from the Deep-Sea-Derived Fungus Chaetomium globosum MP4-S01-7
Wang, Weiyi; Yang, Jing; Liao, Yan-Yan; Cheng, Gang; Chen, Jing; Cheng, Xiang-Dong; Qin, Jiang-Jiang; Shao, Zongze; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b01165

data_1557631
_publ_section_title
;
 Cytotoxic Nitrogenated Azaphilones from the Deep-Sea-Derived Fungus
 Chaetomium globosum MP4-S01-7
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01165
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H25 Cl O6'
_chemical_formula_sum            'C23 H25 Cl O6'
_chemical_formula_weight         432.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.932(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1671(8)
_cell_length_b                   5.4176(4)
_cell_length_c                   16.7266(11)
_cell_measurement_reflns_used    3688
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.019
_cell_measurement_theta_min      2.777
_cell_volume                     1049.00(13)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6402
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        65.032
_diffrn_reflns_theta_max         65.032
_diffrn_reflns_theta_min         2.777
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.935
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1668 before and 0.0831 after correction. The Ratio of minimum to maximum transmission is 0.7340. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0620
_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^)+(0.0983P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1701
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                2844
_reflns_number_total             3380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01165_si_002.cif
_cod_data_source_block           0524a_0m
_cod_database_code               1557631
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.710
_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.a Ternary CH refined with riding coordinates:
 C5'(H5'), C11(H11), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C7'(H7'A,H7'B,H7'C), C6'(H6'A,H6'B,H6'C), C14(H14A,H14B,
 H14C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'