#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221361.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221361
loop_
_publ_author_name
'Xiao, Zhu-Ping'
'Peng, Xiao-Chun'
'Wang, Ying-Chun'
_publ_section_title
(E)-2-(4-Methoxyphenyl)-N-(2-pyridyl)-3-(2-pyridylamino)acrylamide
_journal_coeditor_code           HB2919
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o672
_journal_paper_doi               10.1107/S1600536809007089
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H18 N4 O2'
_chemical_formula_moiety         'C20 H18 N4 O2'
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_weight         346.38
_chemical_name_systematic
(E)-2-(4-Methoxyphenyl)-N-(2-pyridyl)-3-(2-pyridylamino)acrylamide
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.74(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.546(2)
_cell_length_b                   12.148(2)
_cell_length_c                   14.006(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1798.3(7)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0838
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3523
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1891
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0712P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.2002
_reflns_number_gt                1452
_reflns_number_total             3523
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2919.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1798.3(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221361
_cod_database_fobs_code          2221361
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.8670(3) 0.3253(3) 0.3474(3) 0.0628(10) Uani d . 1 . .
H H1A 0.9483 0.3244 0.3725 0.075 Uiso calc R 1 . .
O O1 1.3868(3) 0.5123(3) 0.3652(3) 0.1153(14) Uani d . 1 . .
C C1 1.4551(5) 0.4266(5) 0.3437(5) 0.137(3) Uani d . 1 . .
H H1B 1.5434 0.4450 0.3718 0.206 Uiso calc R 1 . .
H H1C 1.4251 0.4168 0.2696 0.206 Uiso calc R 1 . .
H H1D 1.4432 0.3596 0.3750 0.206 Uiso calc R 1 . .
O O2 0.6560(2) 0.5617(3) 0.1480(2) 0.0756(9) Uani d . 1 . .
N N2 0.6813(3) 0.2469(3) 0.3418(3) 0.0752(11) Uani d . 1 . .
C C2 1.2592(4) 0.5024(5) 0.3320(4) 0.0820(15) Uani d . 1 . .
N N3 0.8252(3) 0.6425(3) 0.1344(2) 0.0591(9) Uani d . 1 . .
H H3A 0.9063 0.6471 0.1648 0.071 Uiso calc R 1 . .
C C3 1.1876(4) 0.4216(4) 0.2676(4) 0.0764(13) Uani d . 1 . .
H H3B 1.2254 0.3682 0.2420 0.092 Uiso calc R 1 . .
N N4 0.8483(3) 0.7805(3) 0.0328(3) 0.0635(9) Uani d . 1 . .
C C4 1.0576(4) 0.4195(3) 0.2404(3) 0.0648(11) Uani d . 1 . .
H H4B 1.0096 0.3645 0.1958 0.078 Uiso calc R 1 . .
C C5 0.9974(4) 0.4961(3) 0.2771(3) 0.0568(11) Uani d . 1 . .
C C6 1.0728(4) 0.5774(4) 0.3409(3) 0.0743(13) Uani d . 1 . .
H H6A 1.0356 0.6313 0.3665 0.089 Uiso calc R 1 . .
C C7 1.2003(4) 0.5811(4) 0.3678(4) 0.0874(15) Uani d . 1 . .
H H7A 1.2479 0.6373 0.4107 0.105 Uiso calc R 1 . .
C C8 0.8599(3) 0.4900(3) 0.2477(3) 0.0545(10) Uani d . 1 . .
C C9 0.8061(4) 0.4077(3) 0.2814(3) 0.0583(11) Uani d . 1 . .
H H9A 0.7183 0.4081 0.2566 0.070 Uiso calc R 1 . .
C C10 0.8054(4) 0.2412(3) 0.3773(3) 0.0602(11) Uani d . 1 . .
C C11 0.8757(4) 0.1591(4) 0.4414(4) 0.0797(15) Uani d . 1 . .
H H11A 0.9634 0.1585 0.4652 0.096 Uiso calc R 1 . .
C C12 0.8136(5) 0.0787(4) 0.4691(4) 0.1026(18) Uani d . 1 . .
H H12A 0.8588 0.0216 0.5122 0.123 Uiso calc R 1 . .
C C13 0.6855(5) 0.0816(4) 0.4340(4) 0.0955(17) Uani d . 1 . .
H H13A 0.6416 0.0268 0.4518 0.115 Uiso calc R 1 . .
C C14 0.6240(5) 0.1666(4) 0.3725(4) 0.0884(16) Uani d . 1 . .
H H14A 0.5365 0.1697 0.3499 0.106 Uiso calc R 1 . .
C C15 0.7711(4) 0.5672(3) 0.1737(3) 0.0537(10) Uani d . 1 . .
C C16 0.7672(4) 0.7143(3) 0.0506(3) 0.0559(10) Uani d . 1 . .
C C17 0.6370(4) 0.7165(4) -0.0105(3) 0.0671(12) Uani d . 1 . .
H H17A 0.5812 0.6716 0.0045 0.080 Uiso calc R 1 . .
C C18 0.5952(5) 0.7878(4) -0.0932(4) 0.0870(15) Uani d . 1 . .
H H18A 0.5094 0.7909 -0.1362 0.104 Uiso calc R 1 . .
C C19 0.6782(5) 0.8542(4) -0.1129(4) 0.0860(16) Uani d . 1 . .
H H19A 0.6505 0.9018 -0.1697 0.103 Uiso calc R 1 . .
C C20 0.8027(4) 0.8489(4) -0.0471(4) 0.0811(14) Uani d . 1 . .
H H20A 0.8588 0.8961 -0.0591 0.097 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C10 . . 123.8(3) ?
C9 N1 H1A . . 118.1 ?
C10 N1 H1A . . 118.1 ?
C2 O1 C1 . . 119.0(5) ?
O1 C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C10 N2 C14 . . 116.3(4) ?
O1 C2 C3 . . 125.0(5) ?
O1 C2 C7 . . 116.1(5) ?
C3 C2 C7 . . 118.8(4) ?
C15 N3 C16 . . 128.6(4) ?
C15 N3 H3A . . 115.7 ?
C16 N3 H3A . . 115.7 ?
C2 C3 C4 . . 119.6(5) ?
C2 C3 H3B . . 120.2 ?
C4 C3 H3B . . 120.2 ?
C20 N4 C16 . . 117.9(4) ?
C5 C4 C3 . . 122.4(4) ?
C5 C4 H4B . . 118.8 ?
C3 C4 H4B . . 118.8 ?
C4 C5 C6 . . 116.3(4) ?
C4 C5 C8 . . 120.7(4) ?
C6 C5 C8 . . 123.0(4) ?
C7 C6 C5 . . 122.0(4) ?
C7 C6 H6A . . 119.0 ?
C5 C6 H6A . . 119.0 ?
C6 C7 C2 . . 120.8(5) ?
C6 C7 H7A . . 119.6 ?
C2 C7 H7A . . 119.6 ?
C9 C8 C15 . . 115.4(4) ?
C9 C8 C5 . . 122.2(4) ?
C15 C8 C5 . . 122.3(4) ?
N1 C9 C8 . . 126.7(4) ?
N1 C9 H9A . . 116.7 ?
C8 C9 H9A . . 116.7 ?
N2 C10 C11 . . 123.7(4) ?
N2 C10 N1 . . 117.1(4) ?
C11 C10 N1 . . 119.2(4) ?
C12 C11 C10 . . 118.0(4) ?
C12 C11 H11A . . 121.0 ?
C10 C11 H11A . . 121.0 ?
C11 C12 C13 . . 120.1(5) ?
C11 C12 H12A . . 120.0 ?
C13 C12 H12A . . 120.0 ?
C14 C13 C12 . . 117.9(5) ?
C14 C13 H13A . . 121.0 ?
C12 C13 H13A . . 121.0 ?
N2 C14 C13 . . 124.0(5) ?
N2 C14 H14A . . 118.0 ?
C13 C14 H14A . . 118.0 ?
O2 C15 N3 . . 122.9(4) ?
O2 C15 C8 . . 122.5(4) ?
N3 C15 C8 . . 114.6(4) ?
N4 C16 N3 . . 113.5(3) ?
N4 C16 C17 . . 122.5(4) ?
N3 C16 C17 . . 124.0(4) ?
C18 C17 C16 . . 117.1(4) ?
C18 C17 H17A . . 121.4 ?
C16 C17 H17A . . 121.4 ?
C19 C18 C17 . . 120.6(4) ?
C19 C18 H18A . . 119.7 ?
C17 C18 H18A . . 119.7 ?
C20 C19 C18 . . 118.2(5) ?
C20 C19 H19A . . 120.9 ?
C18 C19 H19A . . 120.9 ?
N4 C20 C19 . . 123.7(5) ?
N4 C20 H20A . . 118.1 ?
C19 C20 H20A . . 118.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9 . 1.352(4) ?
N1 C10 . 1.402(5) ?
N1 H1A . 0.8600 ?
O1 C2 . 1.360(5) ?
O1 C1 . 1.409(6) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
O2 C15 . 1.231(4) ?
N2 C10 . 1.315(5) ?
N2 C14 . 1.343(5) ?
C2 C3 . 1.365(6) ?
C2 C7 . 1.379(6) ?
N3 C15 . 1.344(5) ?
N3 C16 . 1.398(5) ?
N3 H3A . 0.8600 ?
C3 C4 . 1.393(5) ?
C3 H3B . 0.9300 ?
N4 C20 . 1.321(5) ?
N4 C16 . 1.332(5) ?
C4 C5 . 1.379(5) ?
C4 H4B . 0.9300 ?
C5 C6 . 1.380(5) ?
C5 C8 . 1.472(5) ?
C6 C7 . 1.366(6) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C8 C9 . 1.359(5) ?
C8 C15 . 1.466(5) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.368(5) ?
C11 C12 . 1.358(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.358(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.348(6) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C16 C17 . 1.400(5) ?
C17 C18 . 1.368(6) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.364(6) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.361(6) ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A N4 2_745 0.86 2.25 3.079(5) 163
C9 H9A O2 . 0.93 2.33 2.718(5) 104
C9 H9A N2 . 0.93 2.42 2.754(6) 101
C17 H17A O2 . 0.93 2.27 2.850(5) 120
C11 H11A N4 2_745 0.93 2.62 3.396(6) 141
C14 H14A O2 2_645 0.93 2.59 3.378(5) 143
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 O1 C2 C3 . . . . -8.5(8) ?
C1 O1 C2 C7 . . . . 171.2(5) ?
O1 C2 C3 C4 . . . . 179.1(4) ?
C7 C2 C3 C4 . . . . -0.6(7) ?
C2 C3 C4 C5 . . . . -0.7(7) ?
C3 C4 C5 C6 . . . . 1.5(6) ?
C3 C4 C5 C8 . . . . -179.1(4) ?
C4 C5 C6 C7 . . . . -1.0(6) ?
C8 C5 C6 C7 . . . . 179.6(4) ?
C5 C6 C7 C2 . . . . -0.3(7) ?
O1 C2 C7 C6 . . . . -178.6(4) ?
C3 C2 C7 C6 . . . . 1.2(7) ?
C4 C5 C8 C9 . . . . 68.4(5) ?
C6 C5 C8 C9 . . . . -112.2(5) ?
C4 C5 C8 C15 . . . . -106.8(4) ?
C6 C5 C8 C15 . . . . 72.6(5) ?
C10 N1 C9 C8 . . . . -178.4(4) ?
C15 C8 C9 N1 . . . . 178.4(4) ?
C5 C8 C9 N1 . . . . 2.9(6) ?
C14 N2 C10 C11 . . . . 0.5(7) ?
C14 N2 C10 N1 . . . . -179.0(4) ?
C9 N1 C10 N2 . . . . -3.0(6) ?
C9 N1 C10 C11 . . . . 177.5(4) ?
N2 C10 C11 C12 . . . . 0.5(7) ?
N1 C10 C11 C12 . . . . -180.0(4) ?
C10 C11 C12 C13 . . . . -0.4(8) ?
C11 C12 C13 C14 . . . . -0.6(9) ?
C10 N2 C14 C13 . . . . -1.6(7) ?
C12 C13 C14 N2 . . . . 1.7(9) ?
C16 N3 C15 O2 . . . . -10.3(6) ?
C16 N3 C15 C8 . . . . 168.0(4) ?
C9 C8 C15 O2 . . . . 3.7(6) ?
C5 C8 C15 O2 . . . . 179.2(4) ?
C9 C8 C15 N3 . . . . -174.7(3) ?
C5 C8 C15 N3 . . . . 0.8(5) ?
C20 N4 C16 N3 . . . . 177.8(4) ?
C20 N4 C16 C17 . . . . -1.4(6) ?
C15 N3 C16 N4 . . . . 178.7(4) ?
C15 N3 C16 C17 . . . . -2.1(6) ?
N4 C16 C17 C18 . . . . 2.4(6) ?
N3 C16 C17 C18 . . . . -176.8(4) ?
C16 C17 C18 C19 . . . . -1.0(7) ?
C17 C18 C19 C20 . . . . -1.2(8) ?
C16 N4 C20 C19 . . . . -1.0(7) ?
C18 C19 C20 N4 . . . . 2.3(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655736
