Synthesis of (E)-diethyl 6,6'-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates), a new type of 2,2'-azopyridine dyes
da Silva, Daniel Botelho; Samadi, Abdelouahid; Infantes, Lourdes; Carreiras, María do Carmo; Marco-Contelles, José; Tetrahedron Letters 51 (2010) 6278–6281; doi:10.1016/j.tetlet.2010.09.095

data_7106302
_publ_section_title
;
 Synthesis of
 (E)-diethyl 6,6'-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates),
 a new type of 2,2'-azopyridine dyes
;
_journal_issue                   48
_journal_name_full               'Tetrahedron Letters'
_journal_page_first              6278
_journal_page_last               6281
_journal_paper_doi               10.1016/j.tetlet.2010.09.095
_journal_volume                  51
_journal_year                    2010
_chemical_formula_moiety         'C32 H26 N6 O4'
_chemical_formula_sum            'C32 H26 N6 O4'
_chemical_formula_weight         558.59
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-07-13T12:42:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.24
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.581
_cell_length_b                   8.659
_cell_length_c                   24.036
_cell_measurement_temperature    120(2)
_cell_volume                     2814.770
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR2004 (Altomare et al., 1999,J. Appl. Cryst. 32, 115-119)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16382
_diffrn_reflns_theta_full        66.02
_diffrn_reflns_theta_max         66.02
_diffrn_reflns_theta_min         6.07
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.7043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' '
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0006(2)
_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   1.209
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+1.7541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.166
_reflns_number_gt                2092
_reflns_number_total             2379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10641d.txt
_cod_data_source_block           dsb53
_cod_original_cell_volume        2814.8
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7106302