(\±)-trans,cis-4-Hydroxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one: Synthesis and Facile Dimerization to Decahydrodibenzofurans
Victoria L. Paddock; Robert J. Phipps; Almudena Conde-Angulo; Araceli Blanco-Martin; Carles Giró-Mañas; Laetitia J. Martin; Andrew J. P. White; Alan C. Spivey; Journal of Organic Chemistry 76 (2011) 1483–1486; doi:10.1021/jo102314w

data_4026092
_publ_section_title
;
 (\+-)-trans,cis-4-Hydroxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one:
 Synthesis and Facile Dimerization to Decahydrodibenzofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1483
_journal_page_last               1486
_journal_paper_doi               10.1021/jo102314w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C18 H24 O8'
_chemical_formula_sum            'C18 H24 O8'
_chemical_formula_weight         368.37
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.3473(10)
_cell_length_b                   14.7931(14)
_cell_length_c                   17.9988(19)
_cell_measurement_reflns_used    23456
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.3728
_cell_measurement_theta_min      2.9848
_cell_volume                     3553.8(6)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54248
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30716
_diffrn_reflns_theta_full        69.60
_diffrn_reflns_theta_max         69.60
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.29.6 (release 02-03-2006 CrysAlis171 .NET) 
(compiled Mar  2 2006,16:42:47) 
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    1.377
_exptl_crystal_description       prisms
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2975 Friedel pairs'
_refine_ls_abs_structure_Flack   0.26(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6380
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1047P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                5848
_reflns_number_total             6380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102314w_si_002_2.cif
_cod_data_source_block           8
_cod_database_code               4026092