Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical.
Garnsey, Michelle R.; Slutskyy, Yuriy; Jamison, Christopher R.; Zhao, Peng; Lee, Juyeol; Rhee, Young Ho; Overman, Larry E.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02458

data_4033146
_publ_section_title
;
 Short Enantioselective Total Syntheses of Cheloviolenes A and B and
 Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon
 Radical.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02458
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_sum            'C21 H25 N O6'
_chemical_formula_weight         387.42
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                89.1869(16)
_cell_angle_beta                 83.5067(16)
_cell_angle_gamma                74.6777(16)
_cell_formula_units_Z            4
_cell_length_a                   7.9748(9)
_cell_length_b                   14.1924(17)
_cell_length_c                   17.903(2)
_cell_measurement_reflns_used    7554
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.29
_cell_volume                     1941.5(4)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23899
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_min         1.488
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
; 
 Flack x determined using 4172 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1008
_refine_ls_number_reflns         17948
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0741
_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^)+(0.1034P)^2^+1.0961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.2089
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                11844
_reflns_number_total             17948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02458_si_002.cif
_cod_data_source_block           leo296
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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_database_code               4033146
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.989
_exptl_absorpt_special_details
; 
Reflections not merged 
23899 Corrected reflections written to file leo296s.hkl 
Estimated minimum and maximum transmission:  0.6725  0.7457 
The ratio (0.9018) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_shelx_res_checksum              60498
_shelx_hkl_checksum              77924