Emeridones A-F, a Series of 3,5-Demethylorsellinic Acid-Based Meroterpenoids with Rearranged Skeletons from an Endophytic Fungus Emericella sp. TJ29.
Li, Qin; Chen, Chunmei; Cheng, Li; Wei, Mengsha; Dai, Chong; He, Yan; Gong, Jiaojiao; Zhu, Runqi; Li, Xiao-Nian; Liu, Junjun; Wang, Jianping; Zhu, Hucheng; Zhang, Yonghui; The Journal of organic chemistry 84 (2019) 1534–1541; doi:10.1021/acs.joc.8b02830

data_4037561
_publ_section_title
;
 Emeridones A-F, a Series of 3,5-Demethylorsellinic Acid-Based
 Meroterpenoids with Rearranged Skeletons from an Endophytic Fungus
 Emericella sp. TJ29.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1534
_journal_page_last               1541
_journal_paper_doi               10.1021/acs.joc.8b02830
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 O6, 0.5(H2 O)'
_chemical_formula_sum            'C25 H29 O6.5'
_chemical_formula_weight         433.48
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                91.4630(10)
_cell_angle_beta                 90.4070(10)
_cell_angle_gamma                100.6940(10)
_cell_formula_units_Z            2
_cell_length_a                   7.96440(10)
_cell_length_b                   10.50270(10)
_cell_length_c                   12.5674(2)
_cell_measurement_reflns_used    30870
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9370
_cell_measurement_theta_min      3.5180
_cell_volume                     1032.56(2)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.972
_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    -17.00  89.00   0.50    0.50    --    0.00  38.00   0.00  212
  2  \w     -6.00 113.00   0.50    0.50    --   24.00  79.00  32.99  238
  3  \w     13.00 133.00   0.50    0.50    --   44.00  82.00-160.10  240
  4  \w     17.00 137.00   0.50    0.50    --   48.00  81.00   4.05  240
  5  \w     17.00 137.00   0.50    0.50    --   48.00  81.00 -72.84  240
  6  \w     25.00 145.00   0.50    0.50    --   56.00  82.00  38.42  240
  7  \w     30.00 149.00   0.50    0.50    --   60.00  80.00  82.34  238
  8  \w     29.00 149.00   0.50    0.50    --   60.00  82.00 169.45  240
  9  \w     34.00 153.00   0.50    0.50    --   64.00  79.00 -69.43  238
 10  \w     38.00 157.00   0.50    0.50    --   68.00  80.00-153.60  238
 11  \w     37.00 157.00   0.50    0.50    --   68.00  82.00   1.16  240
 12  \w     37.00 157.00   0.50    0.50    --   68.00  81.00 116.85  240
 13  \w     41.00 161.00   0.50    0.50    --   72.00  82.00-129.48  240
 14  \w     43.00 161.00   0.50    0.50    --   72.00  78.00  46.82  236
 15  \w     45.00 165.00   0.50    0.50    --   76.00  81.00 155.68  240
 16  \w     45.00 165.00   0.50    0.50    --   76.00  81.00 -47.80  240
 17  \w     49.00 169.00   0.50    0.50    --   80.00  81.00 -10.93  240
 18  \w     51.00 169.00   0.50    0.50    --   80.00  78.00  73.82  236
 19  \w     59.00 177.00   0.50    0.50    --   88.00  76.00-100.50  236
 20  \w      6.00 119.00   0.50    0.50    --   95.20 -61.00 -90.00  226
 21  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00 120.00  242
 22  \w     66.00 185.00   0.50    0.50    --   95.20  77.00   0.00  238
 23  \w     70.00 185.00   0.50    0.50    --   95.20  66.00-172.12  230
 24  \w     79.00 185.00   0.50    0.50    --   95.20  30.00 150.00  212
 25  \w     76.00 185.00   0.50    0.50    --   95.20  45.00 -30.00  218
 26  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00 -30.00  242
 27  \w     66.00 185.00   0.50    0.50    --   95.20  77.00 150.00  238
 28  \w     66.00 185.00   0.50    0.50    --   95.20  77.00  60.00  238
 29  \w     72.00 185.00   0.50    0.50    --   95.20  61.00-150.00  226
 30  \w     66.00 185.00   0.50    0.50    --   95.20  77.00  30.00  238
 31  \w     66.00 185.00   0.50    0.50    --   95.20  77.00 -30.00  238
 32  \w      6.00 127.00   0.50    0.50    --   95.20 -82.00-180.00  242
 33  \w     64.00 185.00   0.50    0.50    --   95.20  82.00  90.00  242
 34  \w     64.00 185.00   0.50    0.50    --   95.20  82.00-150.00  242
 35  \w     76.00 185.00   0.50    0.50    --   95.20  45.00 120.00  218
 36  \w     66.00 185.00   0.50    0.50    --   95.20  77.00 120.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1960355000
_diffrn_orient_matrix_UB_12      0.0406765000
_diffrn_orient_matrix_UB_13      -0.0009523000
_diffrn_orient_matrix_UB_21      0.0086774000
_diffrn_orient_matrix_UB_22      -0.0979823000
_diffrn_orient_matrix_UB_23      -0.0922107000
_diffrn_orient_matrix_UB_31      -0.0158084000
_diffrn_orient_matrix_UB_32      0.1050935000
_diffrn_orient_matrix_UB_33      -0.0808406000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35184
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.283
_diffrn_reflns_theta_min         3.518
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44220
_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            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3738 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         7885
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0521P)^2^+0.2216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                7847
_reflns_number_total             7885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02830_si_004.cif
_cod_data_source_block           18-1-2
_cod_original_formula_sum        'C25 H29 O6.50'
_cod_database_code               4037561
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.866
_reflns_odcompleteness_completeness 99.32
_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.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C11(H11), C00I(H00I), C00T(H00T), C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 C9'(H9'A,H9'B), C1'(H1'A,H1'B), C017(H01G,H01H), C12(H12A,H12B), C01A(H01I,
 H01J), C01D(H01K,H01L), C6(H6A,H6B), C7(H7A,H7B), C01J(H01P,H01Q), C01N(H01X,
 H01Y)
2.d Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C1(H1), C6'(H6'), C00R(H00R), C2(H2), C012(H012)
2.e Idealised Me refined as rotating group:
 C10'(H10A,H10B,H10C), C01I(H01M,H01N,H01O), C01K(H01R,H01S,H01T), C13(H13A,
 H13B,H13C), C01M(H01U,H01V,H01W), C01P(H01A,H01B,H01C), C01Q(H01Z,H,HA),
 C01R(H01D,H01E,H01F)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O003(H003)
;
_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 2.231
_oxdiff_exptl_absorpt_empirical_full_min 0.564