Deoxygenation of Hydroquinones as a General Route to Norbornane-Fused Aromatic Systems: An Entry into Substituted and Functionalized Dimethano- and Methanoanthracenes
Prasad Ganji; Hasim Ibrahim; Journal of Organic Chemistry 77 (2012) 511–518; doi:10.1021/jo202023w

data_4026855
_publ_section_title
;
 Deoxygenation of Hydroquinones as a General Route to Norbornane-Fused
 Aromatic Systems: An Entry into Substituted and Functionalized Dimethano-
 and Methanoanthracenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              511
_journal_page_last               518
_journal_paper_doi               10.1021/jo202023w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H16 O'
_chemical_formula_sum            'C16 H16 O'
_chemical_formula_weight         224.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.773(7)
_cell_angle_beta                 92.481(7)
_cell_angle_gamma                99.717(8)
_cell_formula_units_Z            1
_cell_length_a                   5.7182(5)
_cell_length_b                   5.9604(6)
_cell_length_c                   8.6336(7)
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4089
_cell_measurement_theta_min      5.1656
_cell_volume                     287.41(5)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6566
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.61
_diffrn_reflns_theta_min         5.17
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       rod
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.1840
_exptl_crystal_size_mid          0.0626
_exptl_crystal_size_min          0.0296
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0478P)^2^+0.1182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1108
_reflns_number_total             1198
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202023w_si_001.cif
_cod_data_source_block           has25
_cod_original_cell_volume        287.41(4)
_cod_database_code               4026855