#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150264.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_7150264
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            'C23 H24 N4 O4'
_chemical_formula_weight         420.46
_chemical_name_systematic
;
2-Anilino-6-(N-tert-butyloxycarbonylmethylanilino)-3-nitropyridine
;
_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                90.00
_cell_angle_beta                 108.06(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6072(17)
_cell_length_b                   24.695(4)
_cell_length_c                   11.851(3)
_cell_measurement_temperature    173(2)
_cell_volume                     2116.6(9)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'IPDS system of STOE'
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16630
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9641
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0071(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                2797
_reflns_number_total             4066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b508819b.txt
_cod_data_source_block           7c
_cod_original_cell_volume        2116.7(8)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7150264
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, 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
O1 O 0.20353(16) 0.13283(4) 0.18974(11) 0.0464(3) Uani 1 1 d . . .
O2 O 0.3814(2) 0.12317(4) 0.36941(13) 0.0746(5) Uani 1 1 d . . .
O3 O 0.00996(13) 0.43862(4) 0.14412(8) 0.0301(2) Uani 1 1 d . . .
O4 O 0.05095(14) 0.39888(4) 0.32288(9) 0.0331(2) Uani 1 1 d . . .
N1 N 0.28035(16) 0.30057(4) 0.22199(10) 0.0280(3) Uani 1 1 d . . .
N2 N 0.3048(2) 0.15263(5) 0.28478(13) 0.0452(4) Uani 1 1 d . . .
N3 N 0.13910(18) 0.23018(5) 0.09633(11) 0.0348(3) Uani 1 1 d . . .
HN3 H 0.127(3) 0.1945(8) 0.0921(16) 0.055(5) Uiso 1 1 d . . .
N4 N 0.41494(15) 0.37300(4) 0.33724(10) 0.0277(3) Uani 1 1 d . . .
C1 C 0.52525(19) 0.39766(5) 0.44638(12) 0.0274(3) Uani 1 1 d . . .
C2 C 0.7105(2) 0.40706(5) 0.46399(13) 0.0333(3) Uani 1 1 d . . .
H2 H 0.7653 0.3963 0.4056 0.040 Uiso 1 1 calc R . .
C3 C 0.8162(2) 0.43224(6) 0.56711(14) 0.0393(4) Uani 1 1 d . . .
H3 H 0.9436 0.4390 0.5790 0.047 Uiso 1 1 calc R . .
C4 C 0.7378(2) 0.44758(6) 0.65278(14) 0.0387(4) Uani 1 1 d . . .
H4 H 0.8108 0.4650 0.7233 0.046 Uiso 1 1 calc R . .
C5 C 0.5537(2) 0.43755(6) 0.63553(15) 0.0450(4) Uani 1 1 d . . .
H5 H 0.5000 0.4474 0.6950 0.054 Uiso 1 1 calc R . .
C6 C 0.4459(2) 0.41316(6) 0.53203(14) 0.0401(4) Uani 1 1 d . . .
H6 H 0.3180 0.4071 0.5198 0.048 Uiso 1 1 calc R . .
C7 C 0.30632(19) 0.40828(5) 0.24383(13) 0.0272(3) Uani 1 1 d . . .
H7A H 0.3073 0.3938 0.1662 0.033 Uiso 1 1 calc R . .
H7B H 0.3645 0.4446 0.2537 0.033 Uiso 1 1 calc R . .
C8 C 0.10731(19) 0.41394(5) 0.24347(12) 0.0256(3) Uani 1 1 d . . .
C9 C -0.1910(2) 0.44940(6) 0.11925(13) 0.0349(3) Uani 1 1 d . . .
C10 C -0.2921(2) 0.39643(7) 0.11746(15) 0.0459(4) Uani 1 1 d . . .
H10A H -0.2538 0.3702 0.0675 0.055 Uiso 1 1 calc R . .
H10B H -0.4257 0.4025 0.0853 0.055 Uiso 1 1 calc R . .
H10C H -0.2624 0.3822 0.1984 0.055 Uiso 1 1 calc R . .
C11 C -0.2433(2) 0.47430(8) -0.00397(16) 0.0569(5) Uani 1 1 d . . .
H11A H -0.1694 0.5070 -0.0020 0.068 Uiso 1 1 calc R . .
H11B H -0.3748 0.4838 -0.0297 0.068 Uiso 1 1 calc R . .
H11C H -0.2192 0.4482 -0.0597 0.068 Uiso 1 1 calc R . .
C12 C -0.2179(2) 0.48946(6) 0.21002(15) 0.0439(4) Uani 1 1 d . . .
H12A H -0.1671 0.4742 0.2899 0.053 Uiso 1 1 calc R . .
H12B H -0.3501 0.4967 0.1937 0.053 Uiso 1 1 calc R . .
H12C H -0.1537 0.5233 0.2050 0.053 Uiso 1 1 calc R . .
C13 C 0.39009(19) 0.31813(5) 0.32655(12) 0.0270(3) Uani 1 1 d . . .
C14 C 0.4778(2) 0.28313(5) 0.42201(14) 0.0359(4) Uani 1 1 d . . .
H14 H 0.5555 0.2968 0.4955 0.043 Uiso 1 1 calc R . .
C15 C 0.4462(2) 0.22925(6) 0.40414(14) 0.0396(4) Uani 1 1 d . . .
H15 H 0.5022 0.2046 0.4664 0.048 Uiso 1 1 calc R . .
C16 C 0.3330(2) 0.20956(5) 0.29601(14) 0.0357(4) Uani 1 1 d . . .
C17 C 0.2494(2) 0.24728(5) 0.20348(13) 0.0294(3) Uani 1 1 d . . .
C18 C 0.0419(2) 0.25842(5) -0.00753(13) 0.0319(3) Uani 1 1 d . . .
C19 C 0.0250(3) 0.31413(6) -0.01937(15) 0.0523(5) Uani 1 1 d . . .
H19 H 0.0819 0.3369 0.0464 0.063 Uiso 1 1 calc R . .
C20 C -0.0751(3) 0.33654(7) -0.12724(15) 0.0570(5) Uani 1 1 d . . .
H20 H -0.0848 0.3748 -0.1345 0.068 Uiso 1 1 calc R . .
C21 C -0.1602(3) 0.30512(7) -0.22357(15) 0.0472(4) Uani 1 1 d . . .
H21 H -0.2302 0.3211 -0.2966 0.057 Uiso 1 1 calc R . .
C22 C -0.1422(3) 0.24960(7) -0.21245(15) 0.0482(4) Uani 1 1 d . . .
H22 H -0.1988 0.2271 -0.2788 0.058 Uiso 1 1 calc R . .
C23 C -0.0432(2) 0.22652(6) -0.10621(14) 0.0406(4) Uani 1 1 d . . .
H23 H -0.0327 0.1882 -0.1000 0.049 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
C8 O3 C9 120.91(10) . . ?
C13 N1 C17 119.87(11) . . ?
O2 N2 O1 120.48(12) . . ?
O2 N2 C16 119.26(14) . . ?
O1 N2 C16 120.25(13) . . ?
C17 N3 C18 132.05(12) . . ?
C13 N4 C1 121.81(11) . . ?
C13 N4 C7 119.65(12) . . ?
C1 N4 C7 117.86(10) . . ?
C2 C1 C6 119.96(14) . . ?
C2 C1 N4 119.39(12) . . ?
C6 C1 N4 120.63(13) . . ?
C1 C2 C3 119.76(14) . . ?
C4 C3 C2 120.45(15) . . ?
C5 C4 C3 119.61(15) . . ?
C4 C5 C6 120.47(15) . . ?
C1 C6 C5 119.73(15) . . ?
N4 C7 C8 112.91(11) . . ?
O4 C8 O3 126.65(13) . . ?
O4 C8 C7 124.32(13) . . ?
O3 C8 C7 109.02(11) . . ?
O3 C9 C10 109.54(12) . . ?
O3 C9 C11 102.08(11) . . ?
C10 C9 C11 110.84(14) . . ?
O3 C9 C12 109.33(13) . . ?
C10 C9 C12 113.12(13) . . ?
C11 C9 C12 111.34(14) . . ?
N1 C13 N4 115.89(12) . . ?
N1 C13 C14 123.24(12) . . ?
N4 C13 C14 120.87(13) . . ?
C15 C14 C13 117.20(14) . . ?
C14 C15 C16 121.03(14) . . ?
C15 C16 N2 117.64(13) . . ?
C15 C16 C17 118.70(12) . . ?
N2 C16 C17 123.65(14) . . ?
N1 C17 N3 119.01(13) . . ?
N1 C17 C16 119.97(13) . . ?
N3 C17 C16 121.02(12) . . ?
C19 C18 C23 118.20(14) . . ?
C19 C18 N3 125.99(14) . . ?
C23 C18 N3 115.81(12) . . ?
C18 C19 C20 119.86(15) . . ?
C21 C20 C19 121.81(16) . . ?
C20 C21 C22 118.50(16) . . ?
C23 C22 C21 120.61(15) . . ?
C22 C23 C18 121.00(14) . . ?
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
O1 N2 1.2502(18) . ?
O2 N2 1.2299(18) . ?
O3 C8 1.3287(17) . ?
O3 C9 1.4886(17) . ?
O4 C8 1.2074(16) . ?
N1 C13 1.3339(19) . ?
N1 C17 1.3429(17) . ?
N2 C16 1.4222(18) . ?
N3 C17 1.3543(19) . ?
N3 C18 1.4087(19) . ?
N4 C13 1.3686(17) . ?
N4 C1 1.4405(18) . ?
N4 C7 1.4492(17) . ?
C1 C2 1.378(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.385(2) . ?
C3 C4 1.380(2) . ?
C4 C5 1.374(2) . ?
C5 C6 1.384(2) . ?
C7 C8 1.5191(19) . ?
C9 C10 1.514(2) . ?
C9 C11 1.520(2) . ?
C9 C12 1.521(2) . ?
C13 C14 1.416(2) . ?
C14 C15 1.357(2) . ?
C15 C16 1.391(2) . ?
C16 C17 1.429(2) . ?
C18 C19 1.385(2) . ?
C18 C23 1.392(2) . ?
C19 C20 1.384(2) . ?
C20 C21 1.366(2) . ?
C21 C22 1.380(2) . ?
C22 C23 1.375(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9778922
