#------------------------------------------------------------------------------
#$Date: 2018-09-11 16:26:58 +0200 (mar 11 de sep de 2018) $
#$Revision: 210845 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/63/7106302.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7106302
loop_
_publ_author_name
'da Silva, Daniel Botelho'
'Samadi, Abdelouahid'
'Infantes, Lourdes'
'Carreiras, María do Carmo'
'Marco-Contelles, José'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0980P)²+1.7541P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.40161(14) 0.4338(2) 0.53740(8) 0.0248(5) Uani 1 1 d . . .
C2 C 0.39622(14) 0.3259(2) 0.58004(8) 0.0238(5) Uani 1 1 d . . .
C3 C 0.30392(14) 0.2883(2) 0.59814(8) 0.0230(5) Uani 1 1 d . . .
C4 C 0.22150(15) 0.3633(2) 0.57163(8) 0.0245(5) Uani 1 1 d . . .
C5 C 0.23401(14) 0.4721(2) 0.52893(8) 0.0250(5) Uani 1 1 d . . .
C21 C 0.48561(14) 0.2513(2) 0.60367(8) 0.0250(5) Uani 1 1 d . . .
C31 C 0.29835(14) 0.1721(2) 0.64353(8) 0.0242(5) Uani 1 1 d . . .
C32 C 0.35005(15) 0.1978(2) 0.69538(8) 0.0268(5) Uani 1 1 d . . .
C33 C 0.34681(15) 0.0902(3) 0.73782(9) 0.0301(5) Uani 1 1 d . . .
C34 C 0.29443(16) -0.0458(3) 0.72813(9) 0.0326(5) Uani 1 1 d . . .
C35 C 0.24383(16) -0.0727(3) 0.67626(9) 0.0331(6) Uani 1 1 d . . .
C36 C 0.24467(15) 0.0358(2) 0.63408(9) 0.0286(5) Uani 1 1 d . . .
C41 C 0.11725(15) 0.3303(2) 0.58748(8) 0.0233(5) Uani 1 1 d . . .
C42 C 0.01364(16) 0.3200(3) 0.66042(9) 0.0339(6) Uani 1 1 d . . .
H421 H -0.0360(10) 0.3583(8) 0.6322(5) 0.034(6) Uiso 1 1 calc R . .
H422 H 0.0075(2) 0.3772(11) 0.6946(6) 0.039(7) Uiso 1 1 calc R . .
C43 C -0.0039(2) 0.1524(3) 0.67033(11) 0.0465(7) Uani 1 1 d . . .
H431 H 0.0478(12) 0.1126(9) 0.6989(7) 0.063(9) Uiso 1 1 calc R . .
H432 H -0.0007(12) 0.0942(11) 0.6347(6) 0.072(10) Uiso 1 1 calc R . .
H433 H -0.0705(12) 0.1384(5) 0.6840(7) 0.054(8) Uiso 1 1 calc R . .
C51 C 0.14959(15) 0.5610(3) 0.49981(9) 0.0313(5) Uani 1 1 d . . .
H511 H 0.1118(12) 0.4949(14) 0.4747(8) 0.090(12) Uiso 1 1 calc R . .
H512 H 0.1746(5) 0.644(2) 0.4797(8) 0.067(9) Uiso 1 1 calc R . .
H513 H 0.1090(12) 0.600(2) 0.5266(5) 0.085(11) Uiso 1 1 calc R . .
N1 N 0.32324(12) 0.5061(2) 0.51268(7) 0.0262(4) Uani 1 1 d . . .
N11 N 0.49963(12) 0.46822(19) 0.52321(7) 0.0252(4) Uani 1 1 d . . .
N21 N 0.55581(13) 0.1902(2) 0.62226(7) 0.0329(5) Uani 1 1 d . . .
O41 O 0.05115(10) 0.29843(17) 0.55350(6) 0.0319(4) Uani 1 1 d . . .
O42 O 0.11200(10) 0.34521(17) 0.64199(6) 0.0290(4) Uani 1 1 d . . .
H36 H 0.2087(18) 0.017(3) 0.5981(11) 0.034(6) Uiso 1 1 d . . .
H32 H 0.3864(17) 0.294(3) 0.7032(9) 0.028(6) Uiso 1 1 d . . .
H34 H 0.2931(19) -0.117(3) 0.7566(11) 0.039(7) Uiso 1 1 d . . .
H33 H 0.3803(17) 0.109(3) 0.7730(10) 0.029(6) Uiso 1 1 d . . .
H35 H 0.209(2) -0.167(3) 0.6700(11) 0.044(7) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.46(18) . . ?
N1 C1 N11 121.27(17) . . ?
C2 C1 N11 115.21(17) . . ?
C1 C2 C3 119.50(18) . . ?
C1 C2 C21 119.36(17) . . ?
C3 C2 C21 121.12(17) . . ?
C4 C3 C2 116.90(18) . . ?
C4 C3 C31 123.74(17) . . ?
C2 C3 C31 119.37(17) . . ?
C3 C4 C5 119.75(18) . . ?
C3 C4 C41 121.48(17) . . ?
C5 C4 C41 118.77(17) . . ?
N1 C5 C4 122.00(18) . . ?
N1 C5 C51 115.10(17) . . ?
C4 C5 C51 122.88(17) . . ?
N21 C21 C2 179.1(2) . . ?
C32 C31 C36 119.64(19) . . ?
C32 C31 C3 119.50(18) . . ?
C36 C31 C3 120.83(18) . . ?
C33 C32 C31 120.3(2) . . ?
C33 C32 H32 118.7(13) . . ?
C31 C32 H32 120.9(13) . . ?
C34 C33 C32 119.9(2) . . ?
C34 C33 H33 120.2(15) . . ?
C32 C33 H33 119.9(15) . . ?
C33 C34 C35 119.9(2) . . ?
C33 C34 H34 119.3(16) . . ?
C35 C34 H34 120.7(16) . . ?
C36 C35 C34 120.5(2) . . ?
C36 C35 H35 120.4(16) . . ?
C34 C35 H35 119.1(16) . . ?
C35 C36 C31 119.7(2) . . ?
C35 C36 H36 120.2(15) . . ?
C31 C36 H36 120.1(15) . . ?
O41 C41 O42 126.59(19) . . ?
O41 C41 C4 122.07(17) . . ?
O42 C41 C4 111.32(16) . . ?
O42 C42 C43 110.90(19) . . ?
O42 C42 H421 109.5 . . ?
C43 C42 H421 109.5 . . ?
O42 C42 H422 109.5 . . ?
C43 C42 H422 109.5 . . ?
H421 C42 H422 108 . . ?
C42 C43 H431 109.5 . . ?
C42 C43 H432 109.5 . . ?
H431 C43 H432 109.5 . . ?
C42 C43 H433 109.5 . . ?
H431 C43 H433 109.5 . . ?
H432 C43 H433 109.5 . . ?
C5 C51 H511 109.5 . . ?
C5 C51 H512 109.5 . . ?
H511 C51 H512 109.5 . . ?
C5 C51 H513 109.5 . . ?
H511 C51 H513 109.5 . . ?
H512 C51 H513 109.5 . . ?
C1 N1 C5 118.39(17) . . ?
N11 N11 C1 112.9(2) 5_666 . ?
C41 O42 C42 114.73(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.327(3) . ?
C1 C2 1.394(3) . ?
C1 N11 1.435(3) . ?
C2 C3 1.402(3) . ?
C2 C21 1.445(3) . ?
C3 C4 1.396(3) . ?
C3 C31 1.491(3) . ?
C4 C5 1.415(3) . ?
C4 C41 1.526(3) . ?
C5 N1 1.340(3) . ?
C5 C51 1.500(3) . ?
C21 N21 1.145(3) . ?
C31 C32 1.391(3) . ?
C31 C36 1.395(3) . ?
C32 C33 1.385(3) . ?
C32 H32 0.98(2) . ?
C33 C34 1.384(3) . ?
C33 H33 0.94(2) . ?
C34 C35 1.387(3) . ?
C34 H34 0.93(3) . ?
C35 C36 1.383(3) . ?
C35 H35 0.94(3) . ?
C36 H36 0.97(3) . ?
C41 O41 1.190(2) . ?
C41 O42 1.325(2) . ?
C42 O42 1.462(2) . ?
C42 C43 1.494(3) . ?
C42 H421 0.9699 . ?
C42 H422 0.9699 . ?
C43 H431 0.9978 . ?
C43 H432 0.9978 . ?
C43 H433 0.9978 . ?
C51 H511 0.9474 . ?
C51 H512 0.9474 . ?
C51 H513 0.9474 . ?
N11 N11 1.245(3) 5_666 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.7(3) . . . . ?
N11 C1 C2 C3 177.98(17) . . . . ?
N1 C1 C2 C21 178.88(18) . . . . ?
N11 C1 C2 C21 -3.9(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C21 C2 C3 C4 -178.14(17) . . . . ?
C1 C2 C3 C31 179.65(17) . . . . ?
C21 C2 C3 C31 1.5(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C31 C3 C4 C5 179.97(17) . . . . ?
C2 C3 C4 C41 179.39(17) . . . . ?
C31 C3 C4 C41 -0.3(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C41 C4 C5 N1 -179.64(18) . . . . ?
C3 C4 C5 C51 -177.97(19) . . . . ?
C41 C4 C5 C51 2.3(3) . . . . ?
C1 C2 C21 N21 -128(13) . . . . ?
C3 C2 C21 N21 50(13) . . . . ?
C4 C3 C31 C32 -121.6(2) . . . . ?
C2 C3 C31 C32 58.8(2) . . . . ?
C4 C3 C31 C36 60.6(3) . . . . ?
C2 C3 C31 C36 -119.1(2) . . . . ?
C36 C31 C32 C33 -1.3(3) . . . . ?
C3 C31 C32 C33 -179.15(17) . . . . ?
C31 C32 C33 C34 2.0(3) . . . . ?
C32 C33 C34 C35 -1.2(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 C31 1.2(3) . . . . ?
C32 C31 C36 C35 -0.3(3) . . . . ?
C3 C31 C36 C35 177.52(18) . . . . ?
C3 C4 C41 O41 -128.7(2) . . . . ?
C5 C4 C41 O41 51.1(3) . . . . ?
C3 C4 C41 O42 52.6(2) . . . . ?
C5 C4 C41 O42 -127.60(18) . . . . ?
C2 C1 N1 C5 -1.0(3) . . . . ?
N11 C1 N1 C5 -178.07(17) . . . . ?
C4 C5 N1 C1 0.5(3) . . . . ?
C51 C5 N1 C1 178.79(17) . . . . ?
N1 C1 N11 N11 -20.2(3) . . . 5_666 ?
C2 C1 N11 N11 162.5(2) . . . 5_666 ?
O41 C41 O42 C42 -0.4(3) . . . . ?
C4 C41 O42 C42 178.23(16) . . . . ?
C43 C42 O42 C41 85.8(2) . . . . ?
