An Asymmetric, Catalytic (4 + 3) Cycloaddition Reaction of Cyclopentenyl Oxyallylic Cations.
Topinka, Michael; Zawatzky, Kerstin; Barnes, Charles L.; Welch, Christopher J.; Harmata, Michael; Organic letters 19 (2017) 4106–4109; doi:10.1021/acs.orglett.7b01868

data_1546764
_publ_section_title
;
 An Asymmetric, Catalytic (4 + 3) Cycloaddition Reaction of Cyclopentenyl
 Oxyallylic Cations.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4106
_journal_page_last               4109
_journal_paper_doi               10.1021/acs.orglett.7b01868
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H14 O2 Se'
_chemical_formula_sum            'C15 H14 O2 Se'
_chemical_formula_weight         305.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9869(2)
_cell_length_b                   10.9322(4)
_cell_length_c                   19.3709(7)
_cell_measurement_reflns_used    7823
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.8
_cell_volume                     1267.83(8)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker VENTURE CMOS area detector'
_diffrn_measurement_method       'shutterless omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11638
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         2.810
_diffrn_source                   'Incoatec IMuS microfocus Mo tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    2.952
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 G\"ottingen, Germany).
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       Needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0170P)^2^+0.0460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0551
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2747
_reflns_number_total             3117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01868_si_004.cif
_cod_data_source_block           MT-X-153-A2
_cod_original_cell_volume        1267.82(8)
_cod_database_code               1546764
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.471
_shelx_estimated_absorpt_t_max   0.943
_shelx_res_checksum              36271
_shelx_hkl_checksum              64884