Total Synthesis of Nominal <i>ent</i>-Chlorabietol B.
Li, Yulong; Xu, Zhezhe; Xie, Zhipeng; Guan, Xingchao; Xie, Zhixiang; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00233

data_4038147
_publ_section_title
;
 Total Synthesis of Nominal <i>ent</i>-Chlorabietol B.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00233
_journal_year                    2020
_chemical_formula_moiety         'C49 H50 O8'
_chemical_formula_sum            'C49 H50 O8'
_chemical_formula_weight         766.89
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.276(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5804(5)
_cell_length_b                   17.8970(6)
_cell_length_c                   12.2550(5)
_cell_measurement_reflns_used    5291
_cell_measurement_temperature    293.10(10)
_cell_measurement_theta_max      69.8690
_cell_measurement_theta_min      9.7250
_cell_volume                     2098.41(17)
_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      air
_diffrn_ambient_temperature      293.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      8.00  73.00   1.00    1.00    --   54.00 -38.00  60.00   65
  2  \w     96.00 126.00   1.00    1.00    --   54.00  19.00  90.00   30
  3  \w    110.00 142.00   1.00    1.00    --  108.00 -25.00 120.00   32
  4  \w     68.00 120.00   1.00    1.00    --  108.00 -63.00 150.00   52
  5  \w     37.00  70.00   1.00    1.00    --  108.00 -25.00 120.00   33
  6  \w     17.00  47.00   1.00    1.00    --   54.00  19.00  90.00   30
  7  \w     39.00  64.00   1.00    1.00    --    0.00  57.00  30.00   25
  8  \w     30.00  70.00   1.00    1.00    --    0.00  38.00 120.00   40
  9  \w     -7.00  20.00   1.00    1.00    --    0.00  57.00  30.00   27
 10  \w    -20.00  15.00   1.00    1.00    --    0.00  38.00 120.00   35
 11  \w     36.00 115.00   1.00    1.00    --  108.00-111.00 150.00   79
 12  \w      1.00  95.00   1.00    1.00    --   54.00 -99.00 -60.00   94
 13  \w    101.00 127.00   1.00    1.00    --  108.00 -63.00 -90.00   26
 14  \w     40.00  99.00   1.00    1.00    --   54.00  57.00-150.00   59
 15  \w    102.00 178.00   1.00    1.00    --  108.00 111.00-180.00   76
 16  \w    104.00 165.00   1.00    1.00    --  108.00 111.00-150.00   61
 17  \w     89.00 164.00   1.00    1.00    --  108.00  63.00 -60.00   75
 18  \w     13.00  59.00   1.00    1.00    --    0.00  57.00-150.00   46
 19  \w    -69.00 -44.00   1.00    1.00    --    0.00 -57.00 -30.00   25
 20  \w    -33.00  10.00   1.00    1.00    --    0.00 -57.00 -30.00   43
 21  \w     27.00  53.00   1.00    1.00    --   54.00 -19.00  90.00   26
 22  \w     30.00 122.00   1.00    1.00    --   54.00  77.00  30.00   92
 23  \w     57.00 102.00   1.00    1.00    --   54.00-125.00  90.00   45
 24  \w     30.00 104.00   1.00    1.00    --   54.00  77.00  90.00   74
 25  \w    119.00 171.00   1.00    1.00    --  108.00  77.00   0.00   52
 26  \w    141.00 167.00   1.00    1.00    --  108.00  77.00  60.00   26
 27  \w     80.00 106.00   1.00    1.00    --  108.00  77.00   0.00   26
 28  \w     86.00 128.00   1.00    1.00    --  108.00  63.00 -30.00   42
 29  \w     78.00 104.00   1.00    1.00    --  108.00  77.00  30.00   26
 30  \w     86.00 133.00   1.00    1.00    --  108.00  63.00  60.00   47
 31  \w     94.00 120.00   1.00    1.00    --  108.00  50.00 -30.00   26
 32  \w     78.00 103.00   1.00    1.00    --  108.00  77.00  60.00   25
 33  \w     82.00 107.00   1.00    1.00    --  108.00  38.00  60.00   25
 34  \w     79.00 105.00   1.00    1.00    --  108.00  77.00 -30.00   26
 35  \w    129.00 163.00   1.00    1.00    --  108.00  50.00  90.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0584709000
_diffrn_orient_matrix_UB_12      -0.0419474000
_diffrn_orient_matrix_UB_13      -0.0783022000
_diffrn_orient_matrix_UB_21      0.1257475000
_diffrn_orient_matrix_UB_22      -0.0263784000
_diffrn_orient_matrix_UB_23      0.1147872000
_diffrn_orient_matrix_UB_31      -0.0818680000
_diffrn_orient_matrix_UB_32      -0.0703935000
_diffrn_orient_matrix_UB_33      0.0036118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13000
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.989
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31287
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         6954
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0702P)^2^+0.0820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                6280
_reflns_number_total             6954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00233_si_002.cif
_cod_data_source_block           liyl_1118
_cod_original_cell_volume        2098.39(17)
_cod_database_code               4038147
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.97
_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:
 C11(H11), C5AA(H5AA), C9(H9), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C2AA(H2AA,H2AB), C16(H16A,H16B), C20(H20A,H20B), C23(H23A,
 H23B), C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C24(H24), C27(H27), C28(H28), C31(H31),
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39), C41(H41),
  C43(H43), C1BA(H1BA)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C42(H42A,H42B,H42C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              42780
_shelx_hkl_checksum              252
_olex2_date_sample_data_collection 2019-11-18
_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 2.718
_oxdiff_exptl_absorpt_empirical_full_min 0.643