Structural Elucidation and Biomimetic Synthesis of (±)-Cochlactone A with Anti-Inflammatory Activity.
Peng, Xing-Rong; Lu, Shuang-Yang; Shao, Li-Dong; Zhou, Lin; Qiu, Ming-Hua; The Journal of organic chemistry 83 (2018) 5516–5522; doi:10.1021/acs.joc.8b00525

data_4034821
_publ_section_title
;
 Structural Elucidation and Biomimetic Synthesis of (+-)-Cochlactone A
 with Anti-Inflammatory Activity.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5516
_journal_page_last               5522
_journal_paper_doi               10.1021/acs.joc.8b00525
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H26 O5'
_chemical_formula_sum            'C21 H26 O5'
_chemical_formula_weight         358.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.085(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5047(3)
_cell_length_b                   17.1549(7)
_cell_length_c                   16.2889(7)
_cell_measurement_reflns_used    9070
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8680
_cell_measurement_theta_min      2.6700
_cell_volume                     1817.31(14)
_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)'
_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 0.985
_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      2.00  60.00   1.00    1.00    --   39.98 -99.00  30.00   58
  2  \w     77.00 120.00   1.00    1.00    --  108.20-125.00 -30.00   43
  3  \w     44.00  96.00   1.00    1.00    --   39.98-125.00-120.00   52
  4  \w     37.00 130.00   1.00    1.00    --  108.20 -61.00-180.00   93
  5  \w     39.00 135.00   1.00    1.00    --  108.20 -30.00 -90.00   96
  6  \w     83.00 112.00   1.00    1.00    --  108.20  45.00  90.00   29
  7  \w     85.00 153.00   1.00    1.00    --  108.20  30.00 150.00   68
  8  \w    149.00 176.00   1.00    1.00    --  108.20  45.00  90.00   27
  9  \w     74.00 108.00   1.00    1.00    --  108.20 -94.00 150.00   34
 10  \w     79.00 118.00   1.00    1.00    --  108.20-125.00 120.00   39
 11  \w     42.00 131.00   1.00    1.00    --  108.20 -61.00  60.00   89
 12  \w     43.00 140.00   1.00    1.00    --  108.20 -77.00 -60.00   97
 13  \w     31.00 161.00   1.00    1.00    --  108.20 -15.00 120.00  130
 14  \w    -66.00 -13.00   1.00    1.00    --  -39.98 125.00  30.00   53
 15  \w   -120.00   1.00   1.00    1.00    --  -39.98 -19.00 120.00  121
 16  \w   -112.00 -16.00   1.00    1.00    --  -39.98 -37.00-120.00   96
 17  \w    -60.00  32.00   1.00    1.00    --  -41.23  37.00 -90.00   92
 18  \w     76.00 105.00   1.00    1.00    --   41.23  37.00  90.00   29
 19  \w    101.00 143.00   1.00    1.00    --  106.95  45.00-180.00   42
 20  \w     46.00  76.00   1.00    1.00    --  106.95 -30.00   0.00   30
 21  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00 120.00  108
 22  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00-150.00  108
 23  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00   0.00  100
 24  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00 -30.00  108
 25  \w    -33.00  66.00   1.00    1.00    --   41.23 -37.00 150.00   99
 26  \w     79.00 178.00   1.00    1.00    --  106.95  30.00-120.00   99
 27  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  90.00  104
 28  \w     79.00 172.00   1.00    1.00    --  106.95  30.00 -60.00   93
;
_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      -0.0403581000
_diffrn_orient_matrix_UB_12      -0.0820948000
_diffrn_orient_matrix_UB_13      -0.0350168000
_diffrn_orient_matrix_UB_21      -0.0734348000
_diffrn_orient_matrix_UB_22      -0.0272171000
_diffrn_orient_matrix_UB_23      0.0847447000
_diffrn_orient_matrix_UB_31      -0.2215319000
_diffrn_orient_matrix_UB_32      0.0240863000
_diffrn_orient_matrix_UB_33      -0.0234008000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20837
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.273
_diffrn_reflns_theta_min         2.713
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75738
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Flack x determined using 2695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0936
_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^)+(0.1470P)^2^+5.6348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2703
_refine_ls_wR_factor_ref         0.2747
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                6642
_reflns_number_total             7178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00525_si_002.cif
_cod_data_source_block           b-1
_cod_original_cell_volume        1817.32(13)
_cod_database_code               4034821
_shelx_shelxl_version_number     2017/1
_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 Ternary CH refined with riding coordinates:
 C6'(H6'), C018(H018)
2.b Secondary CH2 refined with riding coordinates:
 C8'(H8'A,H8'B), C15'(H15A,H15B), C2'(H2'A,H2'B), C00T(H00B,H00C), C5'(H5'A,
 H5'B), C00Y(H00D,H00E), C010(H01A,H01B), C011(H01C,H01D), C9'(H9'A,H9'B),
 C016(H01E,H01F), C019(H01G,H01H), C01A(H01I,H01J), C4'(H4'A,H4'B), C10'(H10A,
 H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C00K(H00K), C6(H6), C00R(H00R), C00S(H00S), C3(H3)
2.d Idealised Me refined as rotating group:
 C01C(H01K,H01L,H01M), C01D(H01N,H01O,H01P), C12'(H12A,H12B,H12C), C13'(H13A,
 H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O008(H008), O2(H2), O00A(H00A)
;
_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.601