Two undescribed pairs of isoprenyl hydroxybenzoic acid derivatives from coculture of Pestalotiopsis sp. and Penicillium bialowiezense: enantioseparation and their absolute configurations
Li, Fengli; Huang, Zhangyan; Mo, Shuyuan; Gu, Saisai; Zhang, Sitian; Yang, Beiye; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui; New Journal of Chemistry 46 (2022) 17149–17152; doi:10.1039/D2NJ03531F

data_7061776
_publ_section_title
;
 Two undescribed pairs of isoprenyl hydroxybenzoic acid derivatives from
 coculture of Pestalotiopsis sp. and Penicillium bialowiezense:
 enantioseparation and their absolute configurations
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17149
_journal_page_last               17152
_journal_paper_doi               10.1039/D2NJ03531F
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                107.096(6)
_cell_angle_beta                 100.136(7)
_cell_angle_gamma                93.672(6)
_cell_formula_units_Z            2
_cell_length_a                   4.9574(5)
_cell_length_b                   11.4656(7)
_cell_length_c                   13.0020(8)
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7490
_cell_measurement_theta_min      3.6150
_cell_volume                     690.06(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -14.00  26.00   0.50    0.50    --    0.00 -77.00 -90.00   80
  2  \w     10.00  38.00   0.50    0.50    --   36.00  72.00  64.93   56
  3  \w    -10.00  53.00   0.50    0.50    --   36.00 -42.00-110.30  126
  4  \w     83.00 128.00   0.50    0.50    --   40.00  72.00 177.05   90
  5  \w     16.00  41.00   0.50    0.50    --   40.00  72.00 177.05   50
  6  \w    106.00 131.00   0.50    0.50    --   44.00  71.00 -75.31   50
  7  \w     18.00  49.00   0.50    0.50    --   44.00  71.00 -75.31   62
  8  \w     30.00  57.00   0.50    2.00    --   52.00  67.00-158.11   54
  9  \w     30.00  71.00   0.50    2.00    --   56.00  71.00 -52.19   82
 10  \w     33.00  58.00   0.50    2.00    --   60.00  73.00-131.62   50
 11  \w     97.00 139.00   0.50    2.00    --   60.00  73.00-131.62   84
 12  \w     33.00  63.00   0.50    2.00    --   60.00  75.00  27.96   60
 13  \w     36.00  76.00   0.50    2.00    --   64.00  74.00  77.36   80
 14  \w     40.00  72.00   0.50    2.00    --   64.00  73.00  54.88   64
 15  \w     40.00  66.00   0.50    2.00    --   68.00  74.00  -5.11   52
 16  \w     43.00  74.00   0.50    2.00    --   68.00  73.00  99.21   62
 17  \w     44.00  81.00   0.50    2.00    --   72.00  74.00 128.81   74
 18  \w     47.00  84.00   0.50    2.00    --   72.00  67.00-115.75   74
 19  \w    118.00 163.00   0.50    2.00    --   76.00  67.00 179.54   90
 20  \w     51.00  87.00   0.50    2.00    --   76.00  67.00 179.54   72
 21  \w    136.00 164.00   0.50    2.00    --   76.00  67.00 -77.27   56
 22  \w     52.00  78.00   0.50    2.00    --   76.00  67.00 -77.27   52
 23  \w     94.00 120.00   0.50    2.00    --   76.00  67.00 -77.27   52
 24  \w     54.00  80.00   0.50    2.00    --   80.00  71.00  -2.98   52
 25  \w    112.00 169.00   0.50    2.00    --   80.00  73.00 -25.65  114
 26  \w     54.00  82.00   0.50    2.00    --   80.00  73.00 -25.65   56
 27  \w     71.00 120.00   0.50    2.00    --   94.60  61.00  60.00   98
 28  \w     74.00 151.00   0.50    2.00    --   94.60  61.00 120.00  154
 29  \w     71.00 134.00   0.50    2.00    --   94.60  61.00 -60.00  126
 30  \w    123.00 184.00   0.50    2.00    --   94.60  61.00  60.00  122
 31  \w     73.00 130.00   0.50    2.00    --   94.60  61.00   0.00  114
 32  \w     92.00 132.00   0.50    2.00    --   94.60  82.00 -60.00   80
 33  \w     90.00 126.00   0.50    2.00    --   94.60 -82.00  30.00   72
 34  \w     36.00  63.00   0.50    2.00    --   94.60 -82.00  30.00   54
 35  \w     72.00 131.00   0.50    2.00    --   94.60  61.00-150.00  118
 36  \w     63.00 115.00   0.50    2.00    --   94.60 -61.00 150.00  104
 37  \w     16.00  61.00   0.50    2.00    --   94.60 -61.00 150.00   90
 38  \w     71.00 183.00   0.50    2.00    --   94.60  61.00-120.00  224
 39  \w     73.00 149.00   0.50    2.00    --   94.60  61.00  90.00  152
 40  \w    100.00 184.00   0.50    2.00    --   94.60  82.00 120.00  168
 41  \w    150.00 184.00   0.50    2.00    --   94.60  82.00  60.00   68
 42  \w    135.00 184.00   0.50    2.00    --   94.60  70.00-178.17   98
 43  \w    157.00 182.00   0.50    2.00    --   94.60  61.00 150.00   50
 44  \w     73.00 141.00   0.50    2.00    --   94.60  61.00 150.00  136
 45  \w     26.00 109.00   0.50    2.00    --   94.60 -82.00 150.00  166
 46  \w    149.00 175.00   0.50    2.00    --   94.60  75.00-105.73   52
 47  \w     71.00 140.00   0.50    2.00    --   94.60  75.00-105.73  138
 48  \w     45.00 120.00   0.50    2.00    --   94.60 -82.00 -30.00  150
 49  \w     72.00 111.00   0.50    2.00    --   94.60  70.00-178.17   78
 50  \w     63.00 111.00   0.50    2.00    --   94.60 -61.00   0.00   96
 51  \w    141.00 184.00   0.50    2.00    --   94.60  68.00  13.99   86
 52  \w      6.00  31.00   0.50    2.00    --   94.60 -61.00   0.00   50
 53  \w    133.00 178.00   0.50    2.00    --   94.60  61.00   0.00   90
 54  \w     96.00 126.00   0.50    2.00    --   94.60 -82.00-180.00   60
 55  \w     70.00 130.00   0.50    2.00    --   94.60  68.00  13.99  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1184065000
_diffrn_orient_matrix_UB_12      0.0059619000
_diffrn_orient_matrix_UB_13      -0.1158697000
_diffrn_orient_matrix_UB_21      -0.0823439000
_diffrn_orient_matrix_UB_22      -0.1402863000
_diffrn_orient_matrix_UB_23      -0.0405056000
_diffrn_orient_matrix_UB_31      -0.2835291000
_diffrn_orient_matrix_UB_32      0.0186983000
_diffrn_orient_matrix_UB_33      0.0311372000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12040
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        64.976
_diffrn_reflns_theta_max         64.976
_diffrn_reflns_theta_min         3.633
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28443
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1209P)^2^+0.2766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1917
_reflns_number_total             2344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03531f2.cif
_cod_data_source_block           20200729_lfl5-23-2
_cod_depositor_comments          'Adding full bibliography for 7061776.cif.'
_cod_original_cell_volume        690.06(9)
_cod_database_code               7061776
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.680
_reflns_odcompleteness_completeness 99.76
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C9-O3 \\sim C9A-O3A
 with sigma of 0.02
 C10-O4 \\sim C10A-O4A
 with sigma of 0.02
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C8-O3 \\sim C8-O3A
 with sigma of 0.04
 C9-O4 \\sim C9A-O4A
 with sigma of 0.04
 C10-O3 \\sim C10A-O3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(O3) = Uanis(O4A)
Uanis(O4) = Uanis(O3A)
4. Others
 Sof(H8BC)=Sof(H8BD)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(O3A)=
 Sof(H3A)=Sof(O4A)=Sof(H4A)=1-FVAR(1)
 Sof(H8AA)=Sof(H8AB)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(O3)=
 Sof(H3)=Sof(O4)=Sof(H4)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8AA,H8AB), C8(H8BC,H8BD), C11(H11A,H11B), C10(H10A,H10B), C10A(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C12(H12)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
5.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O3(H3), O4(H4), O3A(H3A), O4A(H4A)
;
_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 2.579
_oxdiff_exptl_absorpt_empirical_full_min 0.461