Highly efficient and practical resolution of 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione and stereoselective synthesis of its chiral diamine derivatives
Wang, Bin; Gu, Zhenhua; Org. Chem. Front. 1 (2014) 271–; doi:10.1039/C4QO00011K

data_1552969
_publ_section_title
;
 Highly efficient and practical resolution of
 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione and stereoselective
 synthesis of its chiral diamine derivatives
;
_journal_issue                   3
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              271
_journal_paper_doi               10.1039/C4QO00011K
_journal_volume                  1
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H14 O2, C17 H11 O2'
_chemical_formula_sum            'C37 H26 O4'
_chemical_formula_weight         534.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1215(7)
_cell_length_b                   11.0922(5)
_cell_length_c                   9.3453(4)
_cell_measurement_reflns_used    1228
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      28.7028
_cell_measurement_theta_min      3.0987
_cell_volume                     1360.17(11)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4423
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.034(3)
_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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0426P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                1685
_reflns_number_total             2565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00011k2.cif
_cod_data_source_block           shelxl
_cod_database_code               1552969
_olex2_refinement_description
;
1. Others
 Fixed Sof: H9A(0.5) H3(0.5)
 Fixed U13: C9(0)
 Fixed U23: C9(0)
 Fixed Uiso: H2(0.12) H13(0.08) H19(0.09) H16(0.101) H2A(0.091) H15(0.109)
 H14(0.1) H18(0.094) H1(0.117) H5(0.131) H7(0.112) H9A(0.146) H3(0.146)
 H6(0.143)
 Fixed X: H2(-0.5735) H13(-0.4099) H19(-0.7569) H16(-0.6827) H2A(-0.8197) H15(-
 0.5523) H14(-0.4159) H18(-0.7609) H1(-0.68) H5(-0.779) H7(-0.9116) C9(-1) H9A(-
 1.0499) H3(-0.9501) H6(-0.6622)
 Fixed Y: H2(0.0963) H13(-0.1078) H19(-0.1041) H16(-0.3734) H2A(0.2243) H15(-
 0.3975) H14(-0.2659) H18(-0.2594) H1(0.1183) H5(-0.1748) H7(-0.1511) C9(0)
 H9A(-0.0393) H3(0.0393) H6(-0.0813)
 Fixed Z: H2(-0.7191) H13(-0.3222) H19(-0.6859) H16(-0.3241) H2A(-0.0667) H15(-
 0.1665) H14(-0.1653) H18(-0.5271) H1(0.0149) H5(-0.1884) H7(-0.3761) H9A(-
 0.4719) H3(-0.4719) H6(-0.0475)
;