HFIP Solvent Enables Alcohols To Act as Alkylating Agents in Stereoselective Heterocyclization.
Zhu, Yuxiang; Colomer, Ignacio; Thompson, Amber L.; Donohoe, Timothy J.; Journal of the American Chemical Society 141 (2019) 6489–6493; doi:10.1021/jacs.9b02198

data_4128256
_publ_section_title
;
 HFIP Solvent Enables Alcohols To Act as Alkylating Agents in
 Stereoselective Heterocyclization.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6489
_journal_page_last               6493
_journal_paper_doi               10.1021/jacs.9b02198
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C26 H30 O3'
_chemical_formula_sum            'C26 H30 O3'
_chemical_formula_weight         390.52
_chemical_melting_point          ?
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-07-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_cell_angle_alpha                90
_cell_angle_beta                 96.2374(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8835(2)
_cell_length_b                   13.7039(3)
_cell_length_c                   11.1974(2)
_cell_measurement_reflns_used    9493
_cell_measurement_temperature    150
_cell_measurement_theta_max      75
_cell_measurement_theta_min      5
_cell_volume                     2117.78(7)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26917
_diffrn_reflns_theta_full        74.832
_diffrn_reflns_theta_max         76.359
_diffrn_reflns_theta_min         4.547
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.0004432
_refine_ls_shift/su_mean         0.0000612
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.53P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1167
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1167
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3682
_reflns_number_total             4397
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.89
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0500
_oxford_refine_ls_scale          5.53(11)
_oxford_reflns_number_all        4397
_oxford_structure_analysis_title 6991
_cod_data_source_file            ja9b02198_si_003.cif
_cod_data_source_block           3v
_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_sg_symbol_H-M      'P 21/c '
_cod_database_code               4128256
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)