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_4020003
_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         'C12 H11 I N2 O2'
_chemical_formula_sum            'C12 H11 I N2 O2'
_chemical_formula_weight         342.13
_chemical_name_systematic
;
N,N-dimethyl (8-iodo-7-hydroxy-6-quinolyl)carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 107.6640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3610(2)
_cell_length_b                   7.7420(2)
_cell_length_c                   15.5390(4)
_cell_measurement_reflns_used    9075
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1187.69(5)
_computing_data_collection
;
DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)
;
_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_collimation    'Nonius miracol'
_diffrn_radiation_detector       'CCD plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_polarisn_norm  ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Fine-focus Sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14007
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_T_max  0.724
_exptl_absorpt_correction_T_min  0.565
_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    1.913
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_ls_extinction_coef       0.0082(7)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.6584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0671
_reflns_number_gt                2106
_reflns_number_total             2331
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4020003