#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150265.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_7150265
loop_
_publ_author_name
'Schmid, Sylvia'
'Röttgen, Martin'
'Thewalt, Ulf'
'Austel, Volkhard'
_publ_section_title
;
 Synthesis and conformational properties of
 2,6-bis-anilino-3-nitropyridines.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3408
_journal_page_last               3421
_journal_paper_doi               10.1039/b508819b
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C18 H16 N4 O2'
_chemical_formula_weight         320.35
_chemical_name_systematic
;
6-Anilino-2-(N-methylanilino)-3-nitropyridine
;
_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
_cell_angle_alpha                107.48(3)
_cell_angle_beta                 95.21(3)
_cell_angle_gamma                102.18(3)
_cell_formula_units_Z            4
_cell_length_a                   10.113(2)
_cell_length_b                   12.417(3)
_cell_length_c                   14.105(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1628.7(7)
_computing_cell_refinement       'IPDS software (STOE, 1997)'
_computing_data_collection       'IPDS software (STOE, 1997)'
_computing_data_reduction        'IPDS software (STOE, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Johnson & Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'STOE IPDS system'
_diffrn_measurement_method       'imaging 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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14892
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9655
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0196(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                3473
_reflns_number_total             5971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b508819b.txt
_cod_data_source_block           7e
_cod_original_cell_volume        1628.5(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.44355(15) 0.33582(12) 0.75337(10) 0.0524(4) Uani 1 1 d . . .
N2 N 0.6369(2) 0.41271(15) 0.56267(13) 0.0690(5) Uani 1 1 d . . .
N3 N 0.64152(17) 0.48084(14) 0.78660(10) 0.0615(4) Uani 1 1 d . . .
N4 N 0.24576(18) 0.18675(14) 0.72379(11) 0.0589(4) Uani 1 1 d . . .
HN4 H 0.179(2) 0.1348(18) 0.6748(14) 0.072(6) Uiso 1 1 d . . .
N5 N 0.95255(16) 0.60443(13) 0.31143(10) 0.0556(4) Uani 1 1 d . . .
N6 N 1.11212(17) 0.90906(14) 0.47017(12) 0.0628(4) Uani 1 1 d . . .
N7 N 1.08552(17) 0.74312(13) 0.25976(10) 0.0602(4) Uani 1 1 d . . .
HN7 H 0.783(3) 0.434(2) 0.4030(18) 0.103(8) Uiso 1 1 d . . .
N8 N 0.81842(19) 0.45624(15) 0.35445(13) 0.0694(5) Uani 1 1 d . . .
O1 O 0.75648(17) 0.43842(13) 0.60558(11) 0.0782(4) Uani 1 1 d . . .
O2 O 0.6092(2) 0.40990(18) 0.47463(11) 0.1134(7) Uani 1 1 d . . .
O3 O 1.17748(16) 0.95838(13) 0.55682(10) 0.0846(5) Uani 1 1 d . . .
O4 O 1.09125(15) 0.96331(12) 0.41207(10) 0.0733(4) Uani 1 1 d . . .
C1 C 0.24552(19) 0.16611(15) 0.81641(12) 0.0531(4) Uani 1 1 d . . .
C2 C 0.3482(2) 0.2192(2) 0.89892(13) 0.0742(6) Uani 1 1 d . . .
H2 H 0.4255 0.2732 0.8959 0.089 Uiso 1 1 calc R . .
C3 C 0.3356(3) 0.1916(2) 0.98681(14) 0.0837(7) Uani 1 1 d . . .
H3 H 0.4050 0.2277 1.0425 0.100 Uiso 1 1 calc R . .
C4 C 0.2239(3) 0.1130(2) 0.99256(15) 0.0795(6) Uani 1 1 d . . .
H4 H 0.2161 0.0958 1.0519 0.095 Uiso 1 1 calc R . .
C5 C 0.1220(3) 0.0587(2) 0.90997(16) 0.0828(7) Uani 1 1 d . . .
H5 H 0.0457 0.0038 0.9131 0.099 Uiso 1 1 calc R . .
C6 C 0.1327(2) 0.08557(18) 0.82285(14) 0.0701(5) Uani 1 1 d . . .
H6 H 0.0629 0.0490 0.7675 0.084 Uiso 1 1 calc R . .
C7 C 0.33644(19) 0.25819(15) 0.69018(12) 0.0520(4) Uani 1 1 d . . .
C8 C 0.3084(2) 0.24660(17) 0.58716(12) 0.0602(5) Uani 1 1 d . . .
H8 H 0.2264 0.1992 0.5467 0.072 Uiso 1 1 calc R . .
C9 C 0.4051(2) 0.30712(17) 0.54960(13) 0.0611(5) Uani 1 1 d . . .
H9 H 0.3907 0.3012 0.4819 0.073 Uiso 1 1 calc R . .
C10 C 0.52613(19) 0.37825(16) 0.61182(12) 0.0547(4) Uani 1 1 d . . .
C11 C 0.53793(19) 0.39844(15) 0.71663(12) 0.0527(4) Uani 1 1 d . . .
C12 C 0.7021(2) 0.58776(16) 0.77096(12) 0.0571(5) Uani 1 1 d . . .
C13 C 0.8426(2) 0.63139(19) 0.79153(16) 0.0748(6) Uani 1 1 d . . .
H13 H 0.8985 0.5913 0.8155 0.090 Uiso 1 1 calc R . .
C14 C 0.8999(3) 0.7350(2) 0.77634(17) 0.0836(7) Uani 1 1 d . . .
H14 H 0.9945 0.7651 0.7902 0.100 Uiso 1 1 calc R . .
C15 C 0.8167(3) 0.79346(19) 0.74069(15) 0.0798(7) Uani 1 1 d . . .
H15 H 0.8555 0.8626 0.7296 0.096 Uiso 1 1 calc R . .
C16 C 0.6771(3) 0.75087(18) 0.72131(14) 0.0717(6) Uani 1 1 d . . .
H16 H 0.6214 0.7914 0.6980 0.086 Uiso 1 1 calc R . .
C17 C 0.6199(2) 0.64814(17) 0.73638(12) 0.0614(5) Uani 1 1 d . . .
H17 H 0.5251 0.6191 0.7232 0.074 Uiso 1 1 calc R . .
C18 C 0.6550(3) 0.4813(2) 0.89074(14) 0.0892(7) Uani 1 1 d . . .
H18A H 0.5801 0.5059 0.9205 0.116 Uiso 1 1 calc R . .
H18B H 0.7400 0.5341 0.9283 0.116 Uiso 1 1 calc R . .
H18C H 0.6536 0.4041 0.8918 0.116 Uiso 1 1 calc R . .
C19 C 0.7737(2) 0.36932(17) 0.25950(13) 0.0607(5) Uani 1 1 d . . .
C20 C 0.7719(3) 0.3897(2) 0.16823(16) 0.0837(7) Uani 1 1 d . . .
H20 H 0.7991 0.4654 0.1667 0.100 Uiso 1 1 calc R . .
C21 C 0.7294(3) 0.2969(2) 0.07931(17) 0.1014(9) Uani 1 1 d . . .
H21 H 0.7302 0.3111 0.0183 0.122 Uiso 1 1 calc R . .
C22 C 0.6867(3) 0.1858(2) 0.07888(18) 0.0967(8) Uani 1 1 d . . .
H22 H 0.6585 0.1244 0.0183 0.116 Uiso 1 1 calc R . .
C23 C 0.6856(2) 0.1651(2) 0.16897(17) 0.0814(6) Uani 1 1 d . . .
H23 H 0.6555 0.0893 0.1696 0.098 Uiso 1 1 calc R . .
C24 C 0.7286(2) 0.25552(18) 0.25806(15) 0.0687(5) Uani 1 1 d . . .
H24 H 0.7275 0.2402 0.3186 0.082 Uiso 1 1 calc R . .
C25 C 0.9037(2) 0.56394(17) 0.38220(13) 0.0584(5) Uani 1 1 d . . .
C26 C 0.9403(2) 0.62826(18) 0.48619(13) 0.0657(5) Uani 1 1 d . . .
H26 H 0.9135 0.5951 0.5346 0.079 Uiso 1 1 calc R . .
C27 C 1.0153(2) 0.73899(19) 0.51266(13) 0.0643(5) Uani 1 1 d . . .
H27 H 1.0396 0.7842 0.5804 0.077 Uiso 1 1 calc R . .
C28 C 1.05682(19) 0.78641(16) 0.43881(12) 0.0558(5) Uani 1 1 d . . .
C29 C 1.03150(19) 0.71235(16) 0.33723(12) 0.0528(4) Uani 1 1 d . . .
C30 C 1.2159(2) 0.82174(15) 0.27433(13) 0.0565(5) Uani 1 1 d . . .
C31 C 1.2413(2) 0.88639(17) 0.21004(15) 0.0685(5) Uani 1 1 d . . .
H31 H 1.1725 0.8799 0.1587 0.082 Uiso 1 1 calc R . .
C32 C 1.3687(3) 0.96015(19) 0.22262(17) 0.0787(6) Uani 1 1 d . . .
H32 H 1.3859 1.0020 0.1784 0.094 Uiso 1 1 calc R . .
C33 C 1.4713(3) 0.97309(19) 0.29956(18) 0.0779(6) Uani 1 1 d . . .
H33 H 1.5565 1.0243 0.3081 0.093 Uiso 1 1 calc R . .
C34 C 1.4465(2) 0.90968(18) 0.36336(16) 0.0711(5) Uani 1 1 d . . .
H34 H 1.5149 0.9184 0.4158 0.085 Uiso 1 1 calc R . .
C35 C 1.3210(2) 0.83332(17) 0.35030(15) 0.0637(5) Uani 1 1 d . . .
H35 H 1.3062 0.7889 0.3927 0.076 Uiso 1 1 calc R . .
C36 C 1.0246(3) 0.66755(18) 0.15665(13) 0.0777(6) Uani 1 1 d . . .
H36A H 1.0474 0.5938 0.1443 0.101 Uiso 1 1 calc R . .
H36B H 1.0598 0.7039 0.1098 0.101 Uiso 1 1 calc R . .
H36C H 0.9268 0.6554 0.1484 0.101 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C7 N1 C11 119.02(14) . . ?
O1 N2 O2 121.55(17) . . ?
O1 N2 C10 120.42(16) . . ?
O2 N2 C10 117.92(19) . . ?
C11 N3 C12 120.65(14) . . ?
C11 N3 C18 118.76(15) . . ?
C12 N3 C18 116.65(16) . . ?
C7 N4 C1 132.69(17) . . ?
C29 N5 C25 119.86(15) . . ?
O4 N6 O3 122.27(17) . . ?
O4 N6 C28 119.64(15) . . ?
O3 N6 C28 118.06(17) . . ?
C29 N7 C30 122.92(15) . . ?
C29 N7 C36 117.08(16) . . ?
C30 N7 C36 117.70(15) . . ?
C25 N8 C19 131.05(16) . . ?
C2 C1 C6 118.84(16) . . ?
C2 C1 N4 125.12(17) . . ?
C6 C1 N4 116.03(16) . . ?
C1 C2 C3 119.7(2) . . ?
C4 C3 C2 121.0(2) . . ?
C3 C4 C5 119.50(19) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C1 120.9(2) . . ?
N1 C7 N4 120.28(15) . . ?
N1 C7 C8 123.13(16) . . ?
N4 C7 C8 116.58(17) . . ?
C9 C8 C7 117.43(18) . . ?
C8 C9 C10 120.15(16) . . ?
C9 C10 C11 118.80(15) . . ?
C9 C10 N2 116.35(16) . . ?
C11 C10 N2 124.26(17) . . ?
N1 C11 N3 115.77(15) . . ?
N1 C11 C10 120.28(16) . . ?
N3 C11 C10 123.95(16) . . ?
C17 C12 C13 119.89(19) . . ?
C17 C12 N3 119.98(18) . . ?
C13 C12 N3 120.13(18) . . ?
C12 C13 C14 119.6(2) . . ?
C15 C14 C13 119.9(2) . . ?
C16 C15 C14 120.6(2) . . ?
C15 C16 C17 119.7(2) . . ?
C16 C17 C12 120.4(2) . . ?
C24 C19 C20 118.1(2) . . ?
C24 C19 N8 117.16(17) . . ?
C20 C19 N8 124.73(19) . . ?
C21 C20 C19 119.7(2) . . ?
C22 C21 C20 121.6(2) . . ?
C21 C22 C23 119.0(2) . . ?
C24 C23 C22 120.4(2) . . ?
C23 C24 C19 121.11(19) . . ?
N5 C25 N8 119.22(17) . . ?
N5 C25 C26 122.62(19) . . ?
N8 C25 C26 118.14(17) . . ?
C27 C26 C25 117.67(17) . . ?
C26 C27 C28 120.23(17) . . ?
C27 C28 C29 118.78(18) . . ?
C27 C28 N6 116.99(16) . . ?
C29 C28 N6 124.02(16) . . ?
N5 C29 N7 115.49(15) . . ?
N5 C29 C28 119.98(15) . . ?
N7 C29 C28 124.52(17) . . ?
C31 C30 C35 118.7(2) . . ?
C31 C30 N7 119.77(18) . . ?
C35 C30 N7 121.46(16) . . ?
C32 C31 C30 119.7(2) . . ?
C31 C32 C33 121.2(2) . . ?
C34 C33 C32 119.3(2) . . ?
C33 C34 C35 120.3(2) . . ?
C34 C35 C30 120.74(18) . . ?
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
N1 C7 1.328(2) . ?
N1 C11 1.343(2) . ?
N2 O1 1.232(2) . ?
N2 O2 1.236(2) . ?
N2 C10 1.427(2) . ?
N3 C11 1.368(2) . ?
N3 C12 1.429(2) . ?
N3 C18 1.461(2) . ?
N4 C7 1.357(2) . ?
N4 C1 1.405(2) . ?
N5 C29 1.330(2) . ?
N5 C25 1.334(2) . ?
N6 O4 1.2370(19) . ?
N6 O3 1.240(2) . ?
N6 C28 1.421(2) . ?
N7 C29 1.382(2) . ?
N7 C30 1.422(2) . ?
N7 C36 1.466(2) . ?
N8 C25 1.350(3) . ?
N8 C19 1.407(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.379(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.355(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.374(3) . ?
C7 C8 1.412(2) . ?
C8 C9 1.351(3) . ?
C9 C10 1.389(3) . ?
C10 C11 1.412(2) . ?
C12 C17 1.378(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.374(3) . ?
C15 C16 1.369(3) . ?
C16 C17 1.371(3) . ?
C19 C24 1.384(3) . ?
C19 C20 1.384(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.353(3) . ?
C22 C23 1.371(3) . ?
C23 C24 1.369(3) . ?
C25 C26 1.414(3) . ?
C26 C27 1.343(3) . ?
C27 C28 1.397(3) . ?
C28 C29 1.416(2) . ?
C30 C31 1.387(2) . ?
C30 C35 1.391(3) . ?
C31 C32 1.376(3) . ?
C32 C33 1.379(3) . ?
C33 C34 1.370(3) . ?
C34 C35 1.374(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9798652
