Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
Shen, Zhigao; Pan, Xixian; Lai, Yisheng; Hu, Jiadong; Wan, Xiaolong; Li, Xiaoge; Zhang, Hui; Xie, Weiqing; Chem. Sci. 6 (2015) 6986–; doi:10.1039/C5SC02485D

data_1529474
_publ_section_title
;
 Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo
 iodo-cycloetherification of allyl alcohols
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              6986
_journal_paper_doi               10.1039/C5SC02485D
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H21 I O'
_chemical_formula_weight         344.22
_chemical_name_systematic
(R)-2-(4-(tert-butyl)phenyl)-2-(iodomethyl)-3,3-dimethyloxirane
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-09-05 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.517(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.448(6)
_cell_length_b                   6.0248(16)
_cell_length_c                   11.443(3)
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.354
_cell_measurement_theta_min      4.780
_cell_volume                     1534.3(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4703
_diffrn_reflns_point_group_measured_fraction_full 0.816
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.795
_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.112
_refine_diff_density_max         1.005
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0427P)^2^+1.8756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.473
_reflns_Friedel_fraction_full    0.589
_reflns_Friedel_fraction_max     0.578
_reflns_number_gt                2322
_reflns_number_total             2451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc02485d2.cif
_cod_data_source_block           cd214501
_cod_depositor_comments
'Adding full bibliography for 1529474--1529475.cif.'
_cod_database_code               1529474
_shelxl_version_number           2013-4
_shelx_res_checksum              74462
_shelx_hkl_checksum              51221