HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived <i>Aspergillus versicolor</i>.
Li, Huaqiang; Xu, Dan; Sun, Weiguang; Yang, Beiye; Li, Fengli; Liu, Mengting; Wang, Jianping; Xue, Yongbo; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 82 (2019) 2181–2188; doi:10.1021/acs.jnatprod.9b00183

data_1552621
_publ_section_title
;
 HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids
 from a Soil-Derived <i>Aspergillus versicolor</i>.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2181
_journal_page_last               2188
_journal_paper_doi               10.1021/acs.jnatprod.9b00183
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H31 N3 O4, 1/3(C H4 O)'
_chemical_formula_sum            'C26.33333 H32.33333 N3 O4.33333'
_chemical_formula_weight         460.22
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-21
_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            12
_cell_length_a                   13.98385(5)
_cell_length_b                   14.15826(5)
_cell_length_c                   36.36322(12)
_cell_measurement_reflns_used    119733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5740
_cell_measurement_theta_min      3.3340
_cell_volume                     7199.44(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            220010
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.052
_diffrn_reflns_theta_min         3.350
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             2952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 6331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     938
_refine_ls_number_reflns         14570
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0639P)^2^+2.4484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                14318
_reflns_number_total             14570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00183_si_004.cif
_cod_data_source_block           20181217_lhq6-4-14
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3(C26 H31 N3 O4), C H4 O'
_cod_original_formula_sum        'C79 H97 N9 O13'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1380.65
_cod_database_code               1552621
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C17B-C16B \\sim C17C-C16B
 with sigma of 0.02
 C17B-C18B \\sim C17C-C18C
 with sigma of 0.02
 C18B-C19B \\sim C18C-C19B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18B) = Uanis(C18C)
Uanis(C17B) = Uanis(C17C)
4. Others
 Sof(H16A)=Sof(H19C)=Sof(H19D)=Sof(C17C)=Sof(H17C)=Sof(H17D)=Sof(C18C)=
 Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(H16B)=Sof(H19A)=Sof(H19B)=Sof(C17B)=Sof(H17A)=Sof(H17B)=Sof(C18B)=
 Sof(H18A)=Sof(H18B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C13A(H13A), C16A(H16C), C13B(H13B), C16B(H16B), C16B(H16A)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12C,H12D), C17(H17E,H17F), C18(H18E,H18F), C19(H19E,H19F), C12A(H12E,
 H12F), C17A(H17G,H17H), C18A(H18G,H18H), C19A(H19G,H19H), C12B(H12A,H12B),
 C19B(H19A,H19B), C19B(H19C,H19D), C17B(H17A,H17B), C18B(H18A,H18B), C17C(H17C,
 H17D), C18C(H18C,H18D)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C25(H25), N1(H1A), C1A(H1AA), C2A(H2AA),
 C6A(H6A), C9A(H9A), C25A(H25A), N1A(H1AB), C1B(H1B), C2B(H2B), C6B(H6B),
 C9B(H9B), C25B(H25B), N1B(H1BA)
5.d X=CH2 refined with riding coordinates:
 C26(H26C,H26D), C26A(H26E,H26F), C26B(H26A,H26B)
5.e Idealised Me refined as rotating group:
 C20(H20D,H20E,H20F), C21(H21D,H21E,H21F), C23(H23D,H23E,H23F), C24(H24D,H24E,
 H24F), C20A(H20G,H20H,H20I), C21A(H21G,H21H,H21I), C23A(H23G,H23H,H23I),
 C24A(H24G,H24H,H24I), C20B(H20A,H20B,H20C), C21B(H21A,H21B,H21C), C23B(H23A,
 H23B,H23C), C24B(H24A,H24B,H24C), C1S(H1SA,H1SB,H1SC)
5.f Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O2A(H2AB)
;
_olex2_submission_special_instructions 'No special instructions were received'