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

data_1558378
_publ_section_title
;
 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         'C36 H47 O3 Si'
_chemical_formula_sum            'C36 H47 O3 Si'
_chemical_formula_weight         555.82
_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   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc24s1qq
_audit_creation_date             2019-12-03
_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                   10.7809(7)
_cell_length_b                   12.9537(10)
_cell_length_c                   23.2649(18)
_cell_measurement_reflns_used    2668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8860
_cell_measurement_theta_min      3.8500
_cell_volume                     3249.0(4)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -80.40    2.00   0.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -90.0000 103

  2 omega  -14.00   12.40   0.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -180.0000 33

  3 omega  -22.00   24.40   0.8000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9981  -38.0000  -30.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0098347000
_diffrn_orient_matrix_UB_12      0.0118834000
_diffrn_orient_matrix_UB_13      -0.0293616000
_diffrn_orient_matrix_UB_21      0.0065182000
_diffrn_orient_matrix_UB_22      -0.0533651000
_diffrn_orient_matrix_UB_23      -0.0062528000
_diffrn_orient_matrix_UB_31      -0.0647588000
_diffrn_orient_matrix_UB_32      -0.0036806000
_diffrn_orient_matrix_UB_33      -0.0050970000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0920
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10558
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68669
_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    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0660P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                4624
_reflns_number_total             6350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02829k2.cif
_cod_data_source_block           191202_s4_ytz
_cod_database_code               1558378
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o2si1
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.71
_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), C5(H5), C9(H9), C10(H10), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              99490
_olex2_submission_special_instructions 'No special instructions were received'