4-Hydroxy Pyridones from Heterologous Expression and Cultivation of the Native Host.
Zhang, Wei-Yang; Zhong, Yue; Yu, Yang; Shi, Dan-Feng; Huang, Hui-Yun; Tang, Xiao-Long; Wang, Yong-Heng; Chen, Guo-Dong; Zhang, Hui-Ping; Liu, Chen-Li; Hu, Dan; Gao, Hao; Yao, Xin-Sheng; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.0c00675

data_1559409
_publ_section_title
;
 4-Hydroxy Pyridones from Heterologous Expression and Cultivation of the
 Native Host.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00675
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H25 N O4'
_chemical_formula_sum            'C21 H25 N O4'
_chemical_formula_weight         355.42
_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             2020-01-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.297(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8720(7)
_cell_length_b                   7.8414(5)
_cell_length_c                   35.3848(17)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.0690
_cell_measurement_theta_min      2.4650
_cell_volume                     4123.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -53.00  33.00   1.00    2.00    --  -41.23  38.00-120.00   86
  2  \w     34.00  92.00   1.00    2.00    --   41.23-125.00 -60.00   58
  3  \w    104.00 132.00   1.00    3.50    --  106.95 -61.00  60.00   28
  4  \w     77.00 105.00   1.00    3.50    --  106.95-125.00  30.00   28
  5  \w     46.00  75.00   1.00    3.50    --  106.95-125.00  30.00   29
  6  \w     35.00  99.00   1.00    3.50    --  106.95 -45.00  60.00   64
  7  \w     35.00 135.00   1.00    3.50    --  106.95 -30.00-150.00  100
  8  \w     78.00 178.00   1.00    3.50    --  106.95  61.00-150.00  100
  9  \w    100.00 178.00   1.00    3.50    --  106.95 125.00 150.00   78
 10  \w   -113.00 -14.00   1.00    2.00    --  -41.23 -57.00  90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0726901000
_diffrn_orient_matrix_UB_12      -0.0690696000
_diffrn_orient_matrix_UB_13      -0.0257737000
_diffrn_orient_matrix_UB_21      0.0730065000
_diffrn_orient_matrix_UB_22      0.0405014000
_diffrn_orient_matrix_UB_23      0.0308123000
_diffrn_orient_matrix_UB_31      -0.0115098000
_diffrn_orient_matrix_UB_32      -0.1793959000
_diffrn_orient_matrix_UB_33      0.0168928000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16490
_diffrn_reflns_point_group_measured_fraction_full 0.694
_diffrn_reflns_point_group_measured_fraction_max 0.662
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.068
_diffrn_reflns_theta_min         2.499
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.00024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     940
_refine_ls_number_reflns         11071
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1912
_reflns_Friedel_coverage         0.272
_reflns_Friedel_fraction_full    0.337
_reflns_Friedel_fraction_max     0.307
_reflns_number_gt                6460
_reflns_number_total             11071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00675_si_002.cif
_cod_data_source_block           3g6
_cod_database_code               1559409
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Rigid bond restraints
 C33, C34
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C34, C35
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C71, C72
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C33 \\sim C34: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C34 \\sim C35: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C71 \\sim C72: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
Uanis(C22) = Uanis(C74)
Uanis(C68) = Uanis(C69)
Uanis(C70) = Uanis(C71)
4.a Ternary CH refined with riding coordinates:
 C23(H23), C4(H4A), C26(H26), C39(H39), C6(H6), C65(H65), C36(H36), C68(H68)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C40(H40A,H40B), C24(H24A,H24B), C70(H70A,H70B), C67(H67A,H67B),
 C28(H28A,H28B), C7(H7A,H7B), C35(H35A,H35B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), N3(H3A), N4(H4B), C20(H20), C45(H45), C60(H60), C49(H49),
 C48(H48), C5'(H5'), C9'(H9'), C54(H54), C51(H51), C58(H58), C52(H52), C6'(H6'),
  C2'(H2'), C14(H14), C15(H15), C57(H57), C8'(H8'), C55(H55), C18(H18), C8(H8),
 C17(H17), C29(H29), C71(H71), C9(H9), C72(H72), C34(H34), C30(H30), C33(H33)
4.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C38(H38A,H38B,
 H38C), C10(H10A,H10B,H10C), C37(H37A,H37B,H37C), C25(H25A,H25B,H25C), C73(H73A,
 H73B,H73C), C69(H69A,H69B,H69C), C66(H66A,H66B,H66C), C32(H32A,H32B,H32C),
 C31(H31A,H31B,H31C)
4.e Idealised tetrahedral OH refined as rotating group:
 O7(H7), O13(H13), O3(H3), O16(H16), O12(H12), O15(H15A), O6(H6A), O4(H4)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              18834
_shelx_hkl_checksum              66386
_shelx_fab_checksum              59467
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.614