Site-Selective Acylation of Natural Products with BINOL-Derived Phosphoric Acids
Li, Junqi; Grosslight, Samantha; Miller, Scott J.; Sigman, Matthew S.; Toste, F. Dean; ACS Catalysis  (2019) 9794–; doi:10.1021/acscatal.9b03535

data_4514894
_publ_section_title
;
 Site-Selective Acylation of Natural Products with BINOL-Derived
 Phosphoric Acids
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9794
_journal_paper_doi               10.1021/acscatal.9b03535
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H30 O3'
_chemical_formula_sum            'C19 H30 O3'
_chemical_formula_weight         306.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.688(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0130(2)
_cell_length_b                   7.4903(2)
_cell_length_c                   22.9488(7)
_cell_measurement_reflns_used    20272
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.5890
_cell_measurement_theta_min      3.8210
_cell_volume                     1701.42(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30266
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        66.567
_diffrn_reflns_theta_max         66.567
_diffrn_reflns_theta_min         3.897
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
; 
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0169(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0526P)^2^+0.6158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2858
_reflns_number_total             2870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03535_si_002.cif
_cod_data_source_block           007b-19028
_cod_database_code               4514894
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              95402
_shelx_hkl_checksum              23129