Palladium-catalyzed asymmetric annulation between aryl iodides and racemic epoxides using a chiral norbornene cocatalyst.
Li, Renhe; Liu, Feipeng; Dong, Guangbin; Organic chemistry frontiers : an international journal of organic chemistry 5 (2018) 3108–3112; doi:10.1039/c8qo00808f

data_4037585
_publ_section_title
;
 Palladium-catalyzed asymmetric annulation between aryl iodides and
 racemic epoxides using a chiral norbornene cocatalyst.
;
_journal_issue                   21
_journal_name_full
'Organic chemistry frontiers : an international journal of organic chemistry'
_journal_page_first              3108
_journal_page_last               3112
_journal_paper_doi               10.1039/c8qo00808f
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H25 N O3 S'
_chemical_formula_sum            'C18 H25 N O3 S'
_chemical_formula_weight         335.45
_space_group_crystal_system      orthorhombic
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_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
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_audit_update_record
;
2018-08-01 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.32
_cell_volume                     1686.1(2)
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

Sheldrick, G. M. (2015).  SHELXT.  Acta Cryst. A71, 3-8.

;
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_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       \w-scans
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_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
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_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.819
_diffrn_reflns_theta_min         2.754
_diffrn_source                   'sealed fine focus tube'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS. G. M. Sheldrick. Apex II release 2010, Bruker AXS, Inc.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prism
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_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
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_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         5259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0416P)^2^+0.3040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4834
_reflns_number_total             5259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00808f2.cif
_cod_data_source_block           shelx
_cod_database_code               4037585
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.937
_shelx_res_checksum              9810
_shelx_hkl_checksum              97129