Asymmetric total syntheses of callistrilones B, G and J
Hu, Li-Jun; Cheng, Min-Jing; Cao, Jia-Qing; Zhong, Li-Ping; Hu, Ya-Jian; Wang, Ying; Wang, Lei; Ye, Wen-Cai; Li, Chuang-Chuang; Organic Chemistry Frontiers 5 (2018) 1506–; doi:10.1039/C8QO00130H

data_1554258
_publ_section_title
;
 Asymmetric total syntheses of callistrilones B, G and J
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1506
_journal_paper_doi               10.1039/C8QO00130H
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_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_block_doi                 10.5517/ccdc.csd.cc1z42sz
_audit_creation_date             2016-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2018-02-01 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.882(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.82030(10)
_cell_length_b                   9.9500(2)
_cell_length_c                   11.3663(2)
_cell_measurement_reflns_used    8310
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5380
_cell_measurement_theta_min      4.4540
_cell_volume                     964.07(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, 2008)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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   -114.00 -11.00   1.00    1.00    --  -40.46 -57.00 -30.00  103
  2  \w   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00-120.00  103
  3  \w   -119.00  -7.00   1.00    1.00    --  -40.46 -77.00 -30.00  112
  4  \w   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00   0.00  103
  5  \w      7.00 119.00   1.00    1.00    --   40.46  77.00 -30.00  112
  6  \w      1.00  82.00   1.00    1.00    --   40.46 -99.00 120.00   81
  7  \w      1.00  82.00   1.00    1.00    --   40.46 -99.00-150.00   81
  8  \w     74.00 178.00   1.00    1.00    --  107.48  77.00 -90.00  104
  9  \w     74.00 178.00   1.00    1.00    --  107.48  77.00 -60.00  104
 10  \w     74.00 178.00   1.00    1.00    --  107.48  77.00  30.00  104
 11  \w     80.00 178.00   1.00    1.00    --  107.48  45.00  30.00   98
 12  \w     23.00 109.00   1.00    1.00    --  107.48 -94.00   0.00   86
 13  \w     23.00 109.00   1.00    1.00    --  107.48 -94.00  60.00   86
 14  \w     77.00 178.00   1.00    1.00    --  107.48  61.00 -30.00  101
 15  \w     77.00 178.00   1.00    1.00    --  107.48  61.00   0.00  101
 16  \w     77.00 178.00   1.00    1.00    --  107.48  61.00  30.00  101
 17  \w     77.00 178.00   1.00    1.00    --  107.48  61.00 -60.00  101
;
_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      0.1308471000
_diffrn_orient_matrix_UB_12      -0.0433345000
_diffrn_orient_matrix_UB_13      -0.0593470000
_diffrn_orient_matrix_UB_21      0.1173788000
_diffrn_orient_matrix_UB_22      -0.0050089000
_diffrn_orient_matrix_UB_23      0.1264567000
_diffrn_orient_matrix_UB_31      -0.0420328000
_diffrn_orient_matrix_UB_32      -0.1484931000
_diffrn_orient_matrix_UB_33      0.0131508000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9166
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.569
_diffrn_reflns_theta_min         4.024
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47752
_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_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_coef       0.0132(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.1358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                3412
_reflns_number_total             3438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00130h2.cif
_cod_data_source_block           ej-3+2ch3
_cod_database_code               1554258
_reflns_odcompleteness_completeness 99.95
_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:
 C8(H8), C2'(H2'), C6'(H6'), C9A(H9AA)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C3'(H3'A,H3'B,H3'C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C), C7'(H7'A,H7'B,
 H7'C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,H9'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              11201
_shelx_hkl_checksum              51310
_shelx_shelxl_version_number     2014/7
_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 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.409