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_7157590
_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_absolute_configuration unk
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-15
_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            4
_cell_length_a                   8.3946(2)
_cell_length_b                   11.4810(3)
_cell_length_c                   15.2872(4)
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    292.64(10)
_cell_measurement_theta_max      69.7020
_cell_measurement_theta_min      7.1230
_cell_volume                     1473.36(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      292.64(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega  -22.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -180.0000 28

  2 omega  -74.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -180.0000 29

  3 omega  -73.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 31

  4 omega  -68.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 28

  5 omega  -64.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000   30.0000 40

  6 omega   40.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 83

  7 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 26

  8 omega   29.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    4.8064 47

  9 omega   49.00   75.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

 10 omega   44.00  128.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 84

 11 omega   76.00  110.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 34

 12 omega   46.00   72.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 26

 13 omega  127.00  176.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -150.0000 49

 14 omega   38.00   85.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 47

 15 omega   45.00   93.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 48

 16 omega   36.00   83.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 47

 17 omega   37.00   90.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 53

 18 omega   45.00   93.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 48

 19 omega   37.00   70.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0436449000
_diffrn_orient_matrix_UB_12      0.1066294000
_diffrn_orient_matrix_UB_13      0.0562846000
_diffrn_orient_matrix_UB_21      -0.0257804000
_diffrn_orient_matrix_UB_22      0.0800031000
_diffrn_orient_matrix_UB_23      -0.0796391000
_diffrn_orient_matrix_UB_31      -0.1763942000
_diffrn_orient_matrix_UB_32      0.0146770000
_diffrn_orient_matrix_UB_33      0.0255845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4707
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         4.817
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0354P)^2^+0.0658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0718
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                2297
_reflns_number_total             2480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01235a2.cif
_cod_data_source_block           tangt_0107
_cod_depositor_comments
;Adding full bibliography for 7157587--7157591.cif.

 Adding full bibliography for 7157587--7157591.cif.
;
_cod_original_cell_volume        1473.35(7)
_cod_database_code               7157590
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.881
_reflns_odcompleteness_completeness 96.83
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4)
;
_shelx_res_checksum              24617
_olex2_date_sample_data_collection 2019-01-07
_olex2_submission_special_instructions 'No special instructions were received'