Efficient and Divergent Total Synthesis of (-)-Epicoccin G and (-)-Rostratin A Enabled by Double C(sp<sup>3</sup>)-H Activation.
Thesmar, Pierre; Baudoin, Olivier; Journal of the American Chemical Society 141 (2019) 15779–15783; doi:10.1021/jacs.9b09359

data_4128304
_publ_section_title
;
 Efficient and Divergent Total Synthesis of (-)-Epicoccin G and
 (-)-Rostratin A Enabled by Double C(sp<sup>3</sup>)-H Activation.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15779
_journal_page_last               15783
_journal_paper_doi               10.1021/jacs.9b09359
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H26 N2 O6'
_chemical_formula_sum            'C22 H26 N2 O6'
_chemical_formula_weight         414.46
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                79.7133(18)
_cell_angle_beta                 87.5882(17)
_cell_angle_gamma                60.4663(16)
_cell_formula_units_Z            2
_cell_length_a                   9.4800(6)
_cell_length_b                   9.5062(6)
_cell_length_c                   13.0768(8)
_cell_measurement_reflns_used    8927
_cell_measurement_temperature    123
_cell_measurement_theta_max      70
_cell_measurement_theta_min      5
_cell_volume                     1007.41(11)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9449
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         70.048
_diffrn_reflns_theta_min         5.371
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             439.997
_exptl_crystal_recrystallization_method
; 
 
;
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 2757 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6362
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.0003489
_refine_ls_shift/su_mean         0.0000588
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.174 0.101 0.449E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0318
_refine_ls_wR_factor_gt          0.0318
_refine_ls_wR_factor_ref         0.0317
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              -12
_reflns_number_gt                6369
_reflns_number_total             6392
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0287
_oxford_refine_ls_scale          0.4031(4)
_oxford_reflns_number_all        6375
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            ja9b09359_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4128304