Harvesting the strain installed by a Paternò-Büchi step in a synthetically useful way: high-yielding photoprotolytic oxametathesis in polycyclic systems.
Valiulin, Roman A.; Kutateladze, Andrei G.; Organic letters 11 (2009) 3886–3889; doi:10.1021/ol901456m

data_1504089
_publ_section_title
;
 Harvesting the strain installed by a Patern\`o-B\"uchi step in a
 synthetically useful way: high-yielding photoprotolytic oxametathesis in
 polycyclic systems.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3886
_journal_page_last               3889
_journal_paper_doi               10.1021/ol901456m
_journal_volume                  11
_journal_year                    2009
_chemical_compound_source        kgroup
_chemical_formula_moiety         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_chemical_name_common            'polycyclic hemiacetal'
_chemical_name_systematic
3-hydroxy-8-(4-pyridyl)-1-(2-thienyl)-2-oxatricyclo[5.2.1.0(4,9)]decane
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.66410(10)
_cell_length_b                   7.83820(10)
_cell_length_c                   18.3358(2)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.6576
_cell_measurement_theta_min      2.3192
_cell_volume                     1524.39(3)
_computing_cell_refinement       'Apex2/SAINT (Bruker)'
_computing_data_collection       'Apex2 (Bruker)'
_computing_data_reduction        'Apex2 (Bruker)'
_computing_molecular_graphics    'XSHELL (Bruker)'
_computing_publication_material  'Apex2/enCIFer (Bruker/CCDC)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 APEXII Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            60084
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldric, G.M.(2009). SADABS Univ of G\"ottingen, Germany'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method 'slow evaporation hexane ethanol'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+0.7575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                4845
_reflns_number_total             5801
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901456m_si_001.cif
_cod_data_source_block           rav28237_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1504089