Total Synthesis of Crotophorbolone
Yu, Tianzi; Sun, Ying; Tu, Canhui; Chen, Ting; Fu, Shaomin; Liu, Bo; Chemical Science  (2020) –; doi:10.1039/D0SC02829K

data_1558377
_publ_section_title
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 Total Synthesis of Crotophorbolone
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02829K
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C41 H56 O4 Si'
_chemical_formula_sum            'C41 H56 O4 Si'
_chemical_formula_weight         640.94
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc24s1pp
_audit_creation_date             2019-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-10 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4985(3)
_cell_length_b                   13.7129(5)
_cell_length_c                   24.4365(7)
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7860
_cell_measurement_theta_min      3.4580
_cell_volume                     3853.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -62.00  -36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000 -180.0000 26

  2 omega  -26.00    5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -19.0000  120.0000 31

  3 omega   -2.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9981   38.0000  120.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0138518000
_diffrn_orient_matrix_UB_12      -0.0203881000
_diffrn_orient_matrix_UB_13      0.0258727000
_diffrn_orient_matrix_UB_21      -0.0214147000
_diffrn_orient_matrix_UB_22      0.0458600000
_diffrn_orient_matrix_UB_23      0.0088485000
_diffrn_orient_matrix_UB_31      -0.0561771000
_diffrn_orient_matrix_UB_32      -0.0124622000
_diffrn_orient_matrix_UB_33      -0.0097477000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11916
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.971
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0410P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                4828
_reflns_number_total             7151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02829k2.cif
_cod_data_source_block           191119_s2_ytz
_cod_database_code               1558377
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o2
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C1(H1), C2(H2A), C3(H3), C5(H5), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
2.d X=CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C29(H29A,H29B,H29C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              73821
_olex2_submission_special_instructions 'No special instructions were received'