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_4033145
_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 ad
_chemical_formula_sum            'C23 H33 N2 O3 S'
_chemical_formula_weight         417.57
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0629(16)
_cell_length_b                   17.1594(18)
_cell_length_c                   18.0137(19)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.26
_cell_volume                     4656.0(9)
_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 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker 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  0.0434
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            57862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.983
_diffrn_reflns_theta_min         1.639
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.256
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
; 
 Flack x determined using 4163 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.006(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         11683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0870P)^2^+2.2598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                10411
_reflns_number_total             11683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02458_si_006.cif
_cod_data_source_block           leo291
_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               4033145
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.959
_exptl_absorpt_special_details
; 
Reflections not merged. 57964 Corrected reflections written to 
file leo291s.hkl. Estimated minimum and maximum transmission: 
0.6904  0.7458. The ratio (0.9257) 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              61948
_shelx_hkl_checksum              32593