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_4128257
_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         'C33 H29 I1 O3'
_chemical_formula_sum            'C33 H29 I O3'
_chemical_formula_weight         600.50
_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             2019-01-16
_audit_creation_method           CRYSTALS_ver_14.61_build_7005
_cell_angle_alpha                90
_cell_angle_beta                 94.2377(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.1120(3)
_cell_length_b                   7.19960(10)
_cell_length_c                   29.2680(3)
_cell_measurement_reflns_used    35874
_cell_measurement_temperature    100
_cell_measurement_theta_max      36
_cell_measurement_theta_min      2
_cell_volume                     5487.22(11)
_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      100
_diffrn_detector                 'Photon counting pixel array (area)'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.116
_diffrn_reflns_av_unetI/netI     0.106
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            90125
_diffrn_reflns_theta_full        28.855
_diffrn_reflns_theta_max         36.072
_diffrn_reflns_theta_min         1.501
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.089
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.76
_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    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2431.986
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         4.05
_refine_diff_density_min         -1.87
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0369
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         15998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0818
_refine_ls_shift/su_max          0.0027937
_refine_ls_shift/su_mean         0.0000817
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0916
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0847
_reflns_limit_h_max              42
_reflns_limit_h_min              -43
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              49
_reflns_limit_l_min              0
_reflns_number_gt                14657
_reflns_number_total             24521
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      0.78
_oxford_refine_ls_r_factor_ref   0.0874
_oxford_refine_ls_scale          1.1208(17)
_oxford_reflns_number_all        24521
_oxford_structure_analysis_title DIA0363
_cod_data_source_file            ja9b02198_si_003.cif
_cod_data_source_block           3ad-derivative
_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_original_formula_sum        'C33 H29 I1 O3'
_cod_database_code               4128257
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)