Asymmetric Kita spirolactonisation catalysed by anti-dimethanoanthracene-based iodoarenes
Stephen J. Murray; Hasim Ibrahim; Chem.Commun. 51 (2015) 2376–; doi:10.1039/C4cc09724F

data_7116455
_publ_section_title
;
 Asymmetric Kita spirolactonisation catalysed by
 anti-dimethanoanthracene-based iodoarenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              2376
_journal_paper_doi               10.1039/C4cc09724F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C16 H17 I'
_chemical_formula_weight         336.20
_chemical_name_systematic
(+/-)-9-Iodo-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-anti-dimethanoanthracene
_chemical_properties_physical    Light-sensitive
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2014-12-17 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.441(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6651(12)
_cell_length_b                   14.1041(16)
_cell_length_c                   17.531(2)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.37
_cell_volume                     2584.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25474
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    2.453
_exptl_absorpt_correction_T_max  0.9300
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/MeOH'
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.480
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+1.0264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                5569
_reflns_number_total             6419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc09724f2.cif
_cod_data_source_block           has02
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7116455