Sporormielones A-E, bioactive novel C-C coupled orsellinic acid derivative dimers, and their biosynthetic origin.
Chen, Guo-Dong; Hu, Dan; Huang, Mei-Juan; Tang, Jia; Wang, Xiao-Xia; Zou, Jian; Xie, Jun; Zhang, Wei-Guang; Guo, Liang-Dong; Yao, Xin-Sheng; Abe, Ikuro; Gao, Hao; Chemical communications (Cambridge, England) 56 (2020) 4607–4610; doi:10.1039/d0cc00855a

data_7126238
_publ_section_title
;
 Sporormielones A-E, bioactive novel C-C coupled orsellinic acid
 derivative dimers, and their biosynthetic origin.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4607
_journal_page_last               4610
_journal_paper_doi               10.1039/d0cc00855a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 O6'
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29
_chemical_name_common            'sporormielone B'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1439(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.17259(16)
_cell_length_b                   11.66700(14)
_cell_length_c                   12.81692(17)
_cell_measurement_reflns_used    17109
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6370
_cell_measurement_theta_min      3.4360
_cell_volume                     1357.79(3)
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00  90.00  100
  2  \w    -69.00  32.00   1.00    1.00    --  -41.11  57.00-120.00  101
  3  \w     13.00 113.00   1.00    1.00    --   41.11  57.00-150.00  100
  4  \w     23.00  97.00   1.00    1.00    --   41.11-125.00 -30.00   74
  5  \w    -33.00  65.00   1.00    1.00    --   41.11 -37.00 -60.00   98
  6  \w    -39.00  82.00   1.00    1.00    --   41.11 -19.00  60.00  121
  7  \w     34.00 122.00   1.00    1.00    --  107.58-125.00  60.00   88
  8  \w     31.00 136.00   1.00    1.00    --  107.58 -30.00   0.00  105
  9  \w     31.00 140.00   1.00    1.00    --  107.58 -77.00  60.00  109
 10  \w     35.00 133.00   1.00    1.00    --  107.58 -45.00 -90.00   98
 11  \w     31.00 136.00   1.00    1.00    --  107.58 -30.00-150.00  105
 12  \w     31.00 136.00   1.00    1.00    --  107.58 -30.00  90.00  105
 13  \w     94.00 178.00   1.00    1.00    --  107.58 125.00 -90.00   84
 14  \w     94.00 178.00   1.00    1.00    --  107.58 125.00 -30.00   84
 15  \w     79.00 178.00   1.00    1.00    --  107.58  30.00  60.00   99
 16  \w     25.00 109.00   1.00    1.00    --  107.58 -94.00 -90.00   84
 17  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 -90.00  100
 18  \w      9.00 117.00   1.00    1.00    --   41.11  77.00  60.00  108
 19  \w     23.00  97.00   1.00    1.00    --   41.11-125.00  90.00   74
 20  \w      9.00 117.00   1.00    1.00    --   41.11  77.00-120.00  108
 21  \w      9.00 117.00   1.00    1.00    --   41.11  77.00 -30.00  108
 22  \w     79.00 178.00   1.00    1.00    --  107.58  30.00 -30.00   99
 23  \w     75.00 178.00   1.00    1.00    --  107.58  77.00-150.00  103
 24  \w     55.00 178.00   1.00    1.00    --  107.58  15.00-120.00  123
 25  \w     75.00 178.00   1.00    1.00    --  107.58  77.00  60.00  103
 26  \w     82.00 178.00   1.00    1.00    --  107.58  45.00   0.00   96
 27  \w     78.00 178.00   1.00    1.00    --  107.58  61.00 -90.00  100
 28  \w     78.00 178.00   1.00    1.00    --  107.58  61.00 150.00  100
 29  \w     75.00 178.00   1.00    1.00    --  107.58  77.00-180.00  103
 30  \w     78.00 178.00   1.00    1.00    --  107.58  61.00 -30.00  100
 31  \w     78.00 178.00   1.00    1.00    --  107.58  61.00 120.00  100
 32  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00  90.00  108
 33  \w   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00 120.00   99
 34  \w   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00-180.00   99
 35  \w   -121.00   0.00   1.00    1.00    --  -41.11 -19.00 150.00  121
 36  \w     13.00  76.00   1.00    1.00    --   41.11  57.00-180.00   63
;
_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      0.0371645000
_diffrn_orient_matrix_UB_12      0.1110581000
_diffrn_orient_matrix_UB_13      0.0632073000
_diffrn_orient_matrix_UB_21      -0.0269504000
_diffrn_orient_matrix_UB_22      0.0700926000
_diffrn_orient_matrix_UB_23      -0.1028169000
_diffrn_orient_matrix_UB_31      -0.1632759000
_diffrn_orient_matrix_UB_32      0.0136738000
_diffrn_orient_matrix_UB_33      0.0135913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27554
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.764
_diffrn_reflns_theta_min         5.150
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61419
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0626P)^2^+0.8309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2539
_reflns_number_total             2724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00855a2.cif
_cod_data_source_block           w1-5-5
_cod_depositor_comments
'Adding full bibliography for 7126234--7126238.cif.'
_cod_database_code               7126238
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 100.00
_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 Secondary CH2 refined with riding coordinates:
 C8(H8B,H8A)
2.b Aromatic/amide H refined with riding coordinates:
 C6'(H6')
2.c Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C1(H1C,H1B,H1A), C8'(H8'A,H8'B,H8'C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1'(H1'), O2(H2), O1(H1), O3(H3)
;
_shelx_res_checksum              65632
_shelx_hkl_checksum              56002
_olex2_date_sample_data_collection 2018-06-26
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.587