Intramolecular Photocycloaddition of 2(5 H)-Furanones to Temporarily Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically Pure Polyfunctionalyzed Cyclobutanes.
Xin, Yangchun; Rodríguez-Santiago, Luís; Sodupe, Mariona; Álvarez-Larena, Angel; Busqué, Félix; Alibés, Ramon; The Journal of organic chemistry 83 (2018) 3188–3199; doi:10.1021/acs.joc.8b00088

data_4035174
_publ_section_title
;
 Intramolecular Photocycloaddition of 2(5 H)-Furanones to Temporarily
 Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically
 Pure Polyfunctionalyzed Cyclobutanes.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3188
_journal_page_last               3199
_journal_paper_doi               10.1021/acs.joc.8b00088
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C9 H12 O4'
_chemical_formula_sum            'C9 H12 O4'
_chemical_formula_weight         184.19
_chemical_name_systematic
;
(1R,3S,9S,12S)-5,7,10-trioxatricyclo[7.3.0.0^3,12^]dodecan-11-one
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2534(4)
_cell_length_b                   8.9301(5)
_cell_length_c                   11.6896(7)
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     861.57(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-Axis Spider diffractometer'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3393
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.891
_diffrn_reflns_theta_min         2.870
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (RIGAKU, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0793
_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^)+(0.1106P)^2^+0.1216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2121
_refine_ls_wR_factor_ref         0.2285
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                1744
_reflns_number_total             2221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00088_si_003.cif
_cod_data_source_block           compound22
_cod_database_code               4035174
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              79958
_shelx_hkl_checksum              93706