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_4128303
_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_compound_source        'Pierre Thesmar'
_chemical_formula_moiety         'C22 H27 N2 O8.50'
_chemical_formula_sum            'C22 H27 N2 O8.5'
_chemical_formula_weight         455.46
_chemical_melting_point          ?
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-06-08
_audit_creation_method           CRYSTALS_ver_14.61_build_6949
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.8830(4)
_cell_length_b                   9.8830(4)
_cell_length_c                   36.809(2)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    123
_cell_measurement_theta_max      69
_cell_measurement_theta_min      4
_cell_volume                     3113.6(2)
_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 0.989
_diffrn_measured_fraction_theta_max 0.976
_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  0.031
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16837
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         69.282
_diffrn_reflns_theta_min         3.602
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1446
_exptl_crystal_recrystallization_method
; 
Cyclohexane / AcOEt
;
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1133 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9809
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.0006589
_refine_ls_shift/su_mean         0.0001010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.58P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0854
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0842
_reflns_limit_h_max              4
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              43
_reflns_limit_l_min              0
_reflns_number_gt                3293
_reflns_number_total             3391
_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   0.0333
_oxford_refine_ls_scale          0.13028(6)
_oxford_reflns_number_all        3378
_oxford_structure_analysis_title 'P3221 in P3(2)21'
_cod_data_source_file            ja9b09359_si_003.cif
_cod_data_source_block           THP_1149_123K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3113.7(2)
_cod_original_sg_symbol_Hall     'P 32 2'
_cod_original_sg_symbol_H-M      'P 32 2 1 '
_cod_original_formula_sum        'C22 H27 N2 O8.50'
_cod_database_code               4128303
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.04(8)
_oxford_bijvoet_difference       0.05(6)
_oxford_refined_flack_x          0.14(14)