Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4 + 3] Cycloaddition/SmI2-Pinacol Coupling.
Hassan, Ahmed H. E.; Lee, Jae Kyun; Pae, Ae Nim; Min, Sun-Joon; Cho, Yong Seo; Organic letters 17 (2015) 2672–2675; doi:10.1021/acs.orglett.5b01054

data_1519848
_publ_section_title
;
 Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular
 [4 + 3] Cycloaddition/SmI2-Pinacol Coupling.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2672
_journal_page_last               2675
_journal_paper_doi               10.1021/acs.orglett.5b01054
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.638(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.8887(9)
_cell_length_b                   18.4179(18)
_cell_length_c                   6.9957(7)
_cell_measurement_reflns_used    5737
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.32
_cell_volume                     1032.52(18)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9954
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1023P)^2^+0.1879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2168
_reflns_number_gt                1285
_reflns_number_total             2353
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol5b01054_si_003.cif
_cod_data_source_block           1301
_cod_depositor_comments
'Adding full bibliography for 1519848--1519849.cif.'
_cod_original_cell_volume        1032.51(18)
_cod_database_code               1519848