Harnessing Anionic Rearrangements on the Benzenoid Ring of Quinoline for the Synthesis of 6,6'-Disubstituted 7,7'-Dihydroxy-8,8'-biquinolyls
Blakemore, Paul R.; Kilner, Colin; Milicevic, Selena D.; The Journal of Organic Chemistry 70 (2005) 373–376; doi:10.1021/jo048258l

data_4020004
_publ_section_title
;
 Harnessing Anionic Rearrangements on the Benzenoid Ring of Quinoline
 for the Synthesis of 6,6'-Disubstituted 7,7'-Dihydroxy-8,8'-biquinolyls
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   1
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              373
_journal_page_last               376
_journal_paper_doi               10.1021/jo048258l
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C28 H28 I2 N4 O4'
_chemical_formula_sum            'C28 H28 I2 N4 O4'
_chemical_formula_weight         738.34
_chemical_name_systematic
;
7,7'-bis(diethylaminocarbonyloxy)-6,6'-diiodo-8,8'-biquinolyl
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.7820(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3233(2)
_cell_length_b                   18.2087(4)
_cell_length_c                   13.2098(3)
_cell_measurement_reflns_used    16214
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2890.71(10)
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'phi-omega scans'
_diffrn_radiation_detector       'CCD plate'
_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  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30034
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_T_max  0.9166
_exptl_absorpt_correction_T_min  0.5862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Using multiple and symmetry-related data
 measurements via the program SORTAV.  See
 R.H. Blessing, Acta Cryst (1995), A51, 33-38.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0372P)^2^+0.5818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                4163
_reflns_number_total             5677
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4020004