Unusual <i>ent</i>-Labdane Diterpenoid Dimers and their Selective Activation of TRPV Channels.
Gao, Suyu; Wang, Dun; Chai, Hao; Xu, Jiamin; Li, Tianyu; Niu, Yingxue; Chen, Xinxin; Qiu, Feng; Li, Yang; Li, Hua; Chen, Lixia; The Journal of organic chemistry 84 (2019) 13595–13603; doi:10.1021/acs.joc.9b01864

data_4034571
_publ_section_title
;
 Unusual <i>ent</i>-Labdane Diterpenoid Dimers and their Selective
 Activation of TRPV Channels.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13595
_journal_page_last               13603
_journal_paper_doi               10.1021/acs.joc.9b01864
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C46 H64 O8'
_chemical_formula_sum            'C46 H64 O8'
_chemical_formula_weight         744.97
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.48940(10)
_cell_length_b                   13.86650(10)
_cell_length_c                   22.2258(2)
_cell_measurement_reflns_used    19972
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4650
_cell_measurement_theta_min      3.1350
_cell_volume                     4157.35(6)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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    -96.00  -2.00   1.00    1.00    --  -41.11 125.00-180.00   94
  2  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00  60.00   81
  3  \w    -33.00  66.00   1.00    1.00    --   41.11 -38.00 -30.00   99
  4  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00-120.00   81
  5  \w     35.00 136.00   1.00    1.00    --  106.95 -61.00 -30.00  101
  6  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 120.00   85
  7  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -90.00  104
  8  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 120.00  100
  9  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-120.00  100
 10  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00   0.00  100
 11  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 120.00  100
 12  \w     81.00 108.00   1.00    1.00    --  106.95  48.00  38.00   27
;
_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      -0.0563486000
_diffrn_orient_matrix_UB_12      -0.0804693000
_diffrn_orient_matrix_UB_13      0.0334559000
_diffrn_orient_matrix_UB_21      -0.0989430000
_diffrn_orient_matrix_UB_22      0.0398830000
_diffrn_orient_matrix_UB_23      -0.0240461000
_diffrn_orient_matrix_UB_31      0.0088724000
_diffrn_orient_matrix_UB_32      -0.0654698000
_diffrn_orient_matrix_UB_33      -0.0557067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.706
_diffrn_reflns_theta_min         3.757
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80077
_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    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       0.00203(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         8233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0478P)^2^+0.4700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                8055
_reflns_number_total             8233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01864_si_002.cif
_cod_data_source_block           ba-e5p-45
_cod_database_code               4034571
_shelx_shelxl_version_number     2018/3
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C15'(H15'), C5'(H5'), C5(H5), C12(H12), C3'(H3'), C9'(H9')
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1'(H1'A,H1'B), C11(H11A,H11B), C6(H6A,H6B), C19(H19A,H19B),
 C1(H1A,H1B), C19'(H19C,H19D), C7(H7A,H7B), C15(H15A,H15B), C6'(H6'A,H6'B),
 C2'(H2'A,H2'B), C7'(H7'A,H7'B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C11'(H11'), C12'(H12'), C14'(H14')
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20'(H20D,H20E,H20F), C23(H23A,H23B,H23C), C18'(H18A,
 H18B,H18C), C22(H22A,H22B,H22C), C18(H18D,H18E,H18F), C22'(H22D,H22E,H22F),
 C23'(H23D,H23E,H23F)
;
_olex2_date_sample_data_collection 2019-04-09
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.672