Construction of a meroterpenoid-like compound collection by precursor-assisted biosynthesis.
Ren, Panlong; Miao, Xinyu; Tang, Ting; Wu, Yueting; Wang, Jing; Zeng, Ying; Li, Yun; Gao, Kun; Yang, Yan-Long; Organic & biomolecular chemistry 18 (2020) 5850–5856; doi:10.1039/d0ob01235a

data_7157588
_publ_section_title
;
 Construction of a meroterpenoid-like compound collection by
 precursor-assisted biosynthesis.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5850
_journal_page_last               5856
_journal_paper_doi               10.1039/d0ob01235a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C16 H20 O4, H2 O'
_chemical_formula_sum            'C16 H22 O5'
_chemical_formula_weight         294.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_Hall           '-P 2a 2ac'
_space_group_name_H-M_alt        'P c c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.6901(5)
_cell_length_b                   12.36143(17)
_cell_length_c                   7.35394(11)
_cell_measurement_reflns_used    8065
_cell_measurement_temperature    294.04(10)
_cell_measurement_theta_max      69.5770
_cell_measurement_theta_min      7.4840
_cell_volume                     2971.70(8)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -21.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   90
  2  \w    -21.00  69.00   1.00    1.00    --    0.00  57.00   0.00   90
  3  \w     24.00 124.00   1.00    2.00    --   54.00  77.00  30.00  100
  4  \w    -15.00  75.00   1.00    2.00    --   54.00 -57.00 -30.00   90
  5  \w     33.00 123.00   1.00    2.00    --   54.00  57.00-180.00   90
  6  \w    -16.00  84.00   1.00    2.00    --   54.00 -77.00 -90.00  100
  7  \w     36.00 116.00   1.00    3.00    --  108.00-111.00 150.00   80
  8  \w     35.00 178.00   1.00    3.00    --  108.00 -12.00   0.00  143
  9  \w     36.00 146.00   1.00    3.00    --  108.00 -91.00   0.00  110
 10  \w     38.00 130.00   1.00    3.00    --  108.00 -50.00 -30.00   92
 11  \w     35.00 142.00   1.00    3.00    --  108.00 -25.00 -90.00  107
 12  \w    -55.00   1.00   1.00    1.00    --    0.00 121.00 135.00   56
 13  \w     77.00 123.00   1.00    2.00    --   54.00 153.00 -65.00   46
 14  \w     33.00 123.00   1.00    2.00    --   54.00  57.00 -60.00   90
 15  \w     36.00 119.00   1.00    3.00    --  108.00-119.00 -39.00   83
 16  \w     38.00 130.00   1.00    3.00    --  108.00 -50.00 120.00   92
 17  \w     74.00 178.00   1.00    3.00    --  108.00  25.00-180.00  104
 18  \w     74.00 178.00   1.00    3.00    --  108.00  25.00  90.00  104
 19  \w    -70.00  30.00   1.00    1.00    --    0.00 -77.00 -60.00  100
 20  \w     24.00 124.00   1.00    2.00    --   54.00  77.00-120.00  100
 21  \w     33.00 123.00   1.00    2.00    --   54.00  57.00 120.00   90
 22  \w     74.00 101.00   1.00    3.00    --  108.00  25.00 -90.00   27
 23  \w     78.00 178.00   1.00    3.00    --  108.00  77.00  90.00  100
 24  \w     74.00 178.00   1.00    3.00    --  108.00  25.00   0.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0467156000
_diffrn_orient_matrix_UB_12      0.0071642000
_diffrn_orient_matrix_UB_13      0.0246830000
_diffrn_orient_matrix_UB_21      -0.0020219000
_diffrn_orient_matrix_UB_22      -0.1235702000
_diffrn_orient_matrix_UB_23      0.0259904000
_diffrn_orient_matrix_UB_31      0.0058325000
_diffrn_orient_matrix_UB_32      0.0146367000
_diffrn_orient_matrix_UB_33      0.2063998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            24301
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49829
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0548P)^2^+1.0401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2312
_reflns_number_total             2633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01235a2.cif
_cod_data_source_block           renpl_1204
_cod_depositor_comments
;Adding full bibliography for 7157587--7157591.cif.

 Adding full bibliography for 7157587--7157591.cif.
;
_cod_original_cell_volume        2971.70(7)
_cod_database_code               7157588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'nature product'
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C6BA(H6BA), C4AA(H4AA), C6AA(H6AA)
3.c Secondary CH2 refined with riding coordinates:
 C7AA(H7AA,H7AB), C21(H21A,H21B)
3.d Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C2AA(H2AA)
3.e Idealised Me refined as rotating group:
 C9AA(H9AA,H9AB,H9AC), C0BA(H0BA,H0BB,H0BC), C22(H22A,H22B,H22C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1BA(H1BA), O3BA(H3BA)
;
_shelx_res_checksum              39358
_olex2_date_sample_data_collection 2019-12-04
_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 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.537