Syntheses and Structures of Isomeric Diaminotriazinyl-Substituted 2,2'-Bipyridines and 1,10-Phenanthrolines
Adam Duong; Thierry Maris; Olivier Lebel; James D. Wuest; Journal of Organic Chemistry 76 (2011) 1333–1341; doi:10.1021/jo102191n

data_4025923
_publ_section_title
;
 Syntheses and Structures of Isomeric Diaminotriazinyl-Substituted
 2,2'-Bipyridines and 1,10-Phenanthrolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1333
_journal_page_last               1341
_journal_paper_doi               10.1021/jo102191n
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         '3(C18 H14 N12), 2(C2 H6 O S), C H2 Cl2'
_chemical_formula_sum            'C59 H56 Cl2 N36 O2 S2'
_chemical_formula_weight         1436.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.221(4)
_cell_angle_beta                 82.535(4)
_cell_angle_gamma                69.260(4)
_cell_formula_units_Z            2
_cell_length_a                   14.5409(13)
_cell_length_b                   14.7369(12)
_cell_length_c                   21.9376(17)
_cell_measurement_reflns_used    7855
_cell_measurement_temperature    150
_cell_measurement_theta_max      59.98
_cell_measurement_theta_min      3.21
_cell_volume                     4351.5(6)
_computing_cell_refinement       'SAINT V7.34A(Bruker AXS, 2007)'
_computing_data_collection       'APEX2  (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.34A(Bruker AXS, 2007)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.860
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            67228
_diffrn_reflns_theta_full        67.63
_diffrn_reflns_theta_max         67.63
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  0.8806
_exptl_absorpt_correction_T_min  0.7221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
Attempts to  model disordered solvent molecules
were unsuccessful. PLATON/SQUEEZE  was used to correct
the data for the presence of the disordered solvent.
A potential solvent volume of 2050.4 \%A^3^, 
47.1 % of the total unit-cell volume, was found.
401 electrons per unit cell worth of scattering were located
in the void. The reported structure is based on the 
PLATON/SQUEEZE corrected data. The actual solvent content is
unknown, so several quantities calculated like empirical formula, density, 
absorption coefficient, F(000) etc. may be incorrect.

Ref:  Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201.
;
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     865
_refine_ls_number_reflns         13545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0780P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                7919
_reflns_number_total             13545
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            COD_J_Org_Chem_76_2011_1333_1341.cif
_cod_data_source_block           jw1329
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4025923