From Chiral ortho-Benzoquinone Monoketals to Nonracemic Indolinocodeines through Diels-Alder and Cope Reactions
Jihong Gao; Josephine Orso Simon; Russell Rodrigo; Abdeljalil Assoud; Journal of Organic Chemistry 78 (2013) 48–58; doi:10.1021/jo3014098

data_4027835
_publ_section_title
;
 From Chiral ortho-Benzoquinone Monoketals to Nonracemic Indolinocodeines
 through Diels-Alder and Cope Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              48
_journal_page_last               58
_journal_paper_doi               10.1021/jo3014098
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C36 H44 O6'
_chemical_formula_weight         572.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   8.9733(18)
_cell_length_b                   19.948(4)
_cell_length_c                   34.123(7)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.37
_cell_volume                     6108(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       w-scan
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            35558
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0.0(1)
_diffrn_standards_interval_time  30
_diffrn_standards_number         6003
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       'Plate fragment'
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00137(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.307
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0607
_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^)+(0.0017P)^2^+4.5801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                4708
_reflns_number_total             5987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3014098_si_002.cif
_cod_data_source_block           rr1223q_final
_cod_database_code               4027835