#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228196.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_2228196
loop_
_publ_author_name
'Yang, Xiao-Hui'
'Zhou, Yong-Hong'
'Hu, Li-Hong'
'Liu, Hong-Jun'
_publ_section_title
;
 2-Amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenylnicotinonitrile
;
_journal_coeditor_code           ZS2068
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2746
_journal_paper_doi               10.1107/S1600536810039127
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H17 N3 O3'
_chemical_formula_moiety         'C20 H17 N3 O3'
_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_weight         347.37
_chemical_name_systematic
;
2-Amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenylnicotinonitrile
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.28(3)
_cell_angle_beta                 68.36(3)
_cell_angle_gamma                84.66(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1320(16)
_cell_length_b                   10.497(2)
_cell_length_c                   10.914(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     844.6(3)
_computing_cell_refinement       'SMART (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (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 four-circle'
_diffrn_measurement_method       'ω/2θ scans'
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3294
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(semi-empirical; North et al., 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0689
_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)+(0.060P)²+0.50P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                1776
_reflns_number_total             3058
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2068.cif
_cod_data_source_block           I
_cod_database_code               2228196
_cod_database_fobs_code          2228196
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.2727(5) -0.1198(2) 1.0345(3) 0.0793(13) Uani . . 1.000
O O2 0.2820(4) -0.0923(2) 0.5979(3) 0.0590(10) Uani . . 1.000
O O3 0.2628(3) -0.2323(2) 0.8421(2) 0.0535(9) Uani . . 1.000
N N1 0.4176(4) 0.5786(2) 0.6850(3) 0.0442(10) Uani . . 1.000
N N2 0.2265(4) 0.6279(3) 0.5721(3) 0.0598(11) Uani . . 1.000
N N3 0.0259(5) 0.3444(3) 0.5868(4) 0.0697(14) Uani . . 1.000
C C1 0.6885(5) 0.6715(3) 0.7396(4) 0.0529(12) Uani . . 1.000
C C2 0.8049(5) 0.7227(4) 0.7807(4) 0.0641(16) Uani . . 1.000
C C3 0.8678(5) 0.6491(4) 0.8747(4) 0.0630(16) Uani . . 1.000
C C4 0.8153(5) 0.5217(4) 0.9273(4) 0.0600(14) Uani . . 1.000
C C5 0.6991(5) 0.4705(3) 0.8868(4) 0.0512(11) Uani . . 1.000
C C6 0.6330(4) 0.5439(3) 0.7930(3) 0.0433(11) Uani . . 1.000
C C7 0.5053(4) 0.4907(3) 0.7504(3) 0.0413(11) Uani . . 1.000
C C8 0.4765(5) 0.3580(3) 0.7747(3) 0.0459(11) Uani . . 1.000
C C9 0.3556(4) 0.3108(3) 0.7332(3) 0.0429(11) Uani . . 1.000
C C10 0.2667(4) 0.4028(3) 0.6648(3) 0.0436(11) Uani . . 1.000
C C11 0.3040(4) 0.5356(3) 0.6404(3) 0.0423(11) Uani . . 1.000
C C12 0.3250(4) 0.1688(3) 0.7618(4) 0.0453(11) Uani . . 1.000
C C13 0.3115(5) 0.0937(3) 0.8868(4) 0.0528(14) Uani . . 1.000
C C14 0.2894(5) -0.0402(3) 0.9136(4) 0.0496(11) Uani . . 1.000
C C15 0.2843(4) -0.1017(3) 0.8137(3) 0.0395(11) Uani . . 1.000
C C16 0.2939(4) -0.0246(3) 0.6902(3) 0.0428(11) Uani . . 1.000
C C17 0.3166(4) 0.1081(3) 0.6633(3) 0.0438(11) Uani . . 1.000
C C18 0.1322(5) 0.3671(3) 0.6226(4) 0.0477(11) Uani . . 1.000
C C19 0.2036(7) -0.0690(5) 1.1506(5) 0.096(2) Uani . . 1.000
C C20 0.2425(5) -0.0191(4) 0.4867(4) 0.0641(16) Uani . . 1.000
H H1B 0.64720 0.72290 0.67560 0.0630 Uiso calc R 1.000
H H2A 0.25100 0.70880 0.55940 0.0720 Uiso calc R 1.000
H H2B 0.15250 0.60600 0.54110 0.0720 Uiso calc R 1.000
H H2C 0.84120 0.80870 0.74410 0.0770 Uiso calc R 1.000
H H3A 0.94520 0.68490 0.90260 0.0750 Uiso calc R 1.000
H H3B 0.25970 -0.26200 0.91900 0.0800 Uiso calc R 1.000
H H4A 0.85840 0.47030 0.99020 0.0720 Uiso calc R 1.000
H H5A 0.66400 0.38430 0.92330 0.0620 Uiso calc R 1.000
H H8A 0.53890 0.29950 0.81940 0.0550 Uiso calc R 1.000
H H13A 0.31720 0.13370 0.95320 0.0640 Uiso calc R 1.000
H H17A 0.32640 0.15730 0.57890 0.0520 Uiso calc R 1.000
H H19A 0.20010 -0.13640 1.22690 0.1430 Uiso calc R 1.000
H H19B 0.08590 -0.03610 1.16140 0.1430 Uiso calc R 1.000
H H19C 0.27690 0.00070 1.14390 0.1430 Uiso calc R 1.000
H H20A 0.23850 -0.07660 0.43050 0.0970 Uiso calc R 1.000
H H20B 0.33230 0.04490 0.43580 0.0970 Uiso calc R 1.000
H H20C 0.12980 0.02400 0.51810 0.0970 Uiso calc R 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O1 C19 . . . 119.3(3) no
C16 O2 C20 . . . 117.4(3) no
C15 O3 H3B . . . 109.00 no
C7 N1 C11 . . . 119.1(3) no
C11 N2 H2B . . . 120.00 no
H2A N2 H2B . . . 120.00 no
C11 N2 H2A . . . 120.00 no
C2 C1 C6 . . . 120.3(4) no
C1 C2 C3 . . . 121.1(4) no
C2 C3 C4 . . . 119.2(4) no
C3 C4 C5 . . . 119.9(4) no
C4 C5 C6 . . . 121.7(3) no
C5 C6 C7 . . . 122.2(3) no
C1 C6 C5 . . . 117.9(3) no
C1 C6 C7 . . . 119.9(3) no
C6 C7 C8 . . . 122.3(3) no
N1 C7 C8 . . . 121.2(3) no
N1 C7 C6 . . . 116.5(3) no
C7 C8 C9 . . . 121.0(3) no
C8 C9 C10 . . . 117.2(3) no
C8 C9 C12 . . . 120.1(3) no
C10 C9 C12 . . . 122.7(3) no
C9 C10 C11 . . . 119.3(3) no
C9 C10 C18 . . . 122.6(3) no
C11 C10 C18 . . . 118.0(3) no
N1 C11 C10 . . . 122.1(3) no
N2 C11 C10 . . . 122.0(3) no
N1 C11 N2 . . . 115.9(3) no
C13 C12 C17 . . . 119.2(3) no
C9 C12 C13 . . . 119.9(3) no
C9 C12 C17 . . . 120.9(3) no
C12 C13 C14 . . . 120.6(3) no
O1 C14 C15 . . . 116.0(3) no
C13 C14 C15 . . . 120.2(3) no
O1 C14 C13 . . . 123.8(3) no
O3 C15 C14 . . . 119.2(3) no
O3 C15 C16 . . . 122.4(3) no
C14 C15 C16 . . . 118.3(3) no
O2 C16 C15 . . . 114.9(3) no
C15 C16 C17 . . . 121.4(3) no
O2 C16 C17 . . . 123.7(3) no
C12 C17 C16 . . . 120.1(3) no
N3 C18 C10 . . . 177.1(4) no
C2 C1 H1B . . . 120.00 no
C6 C1 H1B . . . 120.00 no
C1 C2 H2C . . . 119.00 no
C3 C2 H2C . . . 119.00 no
C2 C3 H3A . . . 120.00 no
C4 C3 H3A . . . 120.00 no
C3 C4 H4A . . . 120.00 no
C5 C4 H4A . . . 120.00 no
C4 C5 H5A . . . 119.00 no
C6 C5 H5A . . . 119.00 no
C7 C8 H8A . . . 120.00 no
C9 C8 H8A . . . 119.00 no
C12 C13 H13A . . . 120.00 no
C14 C13 H13A . . . 120.00 no
C12 C17 H17A . . . 120.00 no
C16 C17 H17A . . . 120.00 no
O1 C19 H19A . . . 109.00 no
O1 C19 H19B . . . 109.00 no
O1 C19 H19C . . . 109.00 no
H19A C19 H19B . . . 109.00 no
H19A C19 H19C . . . 109.00 no
H19B C19 H19C . . . 109.00 no
O2 C20 H20A . . . 109.00 no
O2 C20 H20B . . . 110.00 no
O2 C20 H20C . . . 110.00 no
H20A C20 H20B . . . 109.00 no
H20A C20 H20C . . . 109.00 no
H20B C20 H20C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 . . 1.364(5) no
O1 C19 . . 1.387(6) no
O2 C16 . . 1.389(4) no
O2 C20 . . 1.413(5) no
O3 C15 . . 1.350(4) no
O3 H3B . . 0.8200 no
N1 C7 . . 1.354(4) no
N1 C11 . . 1.342(5) no
N2 C11 . . 1.344(5) no
N3 C18 . . 1.134(6) no
N2 H2B . . 0.8600 no
N2 H2A . . 0.8600 no
C1 C2 . . 1.378(6) no
C1 C6 . . 1.383(5) no
C2 C3 . . 1.370(6) no
C3 C4 . . 1.374(6) no
C4 C5 . . 1.373(6) no
C5 C6 . . 1.383(5) no
C6 C7 . . 1.478(5) no
C7 C8 . . 1.385(5) no
C8 C9 . . 1.391(5) no
C9 C10 . . 1.401(5) no
C9 C12 . . 1.479(5) no
C10 C11 . . 1.401(5) no
C10 C18 . . 1.440(5) no
C12 C17 . . 1.389(5) no
C12 C13 . . 1.388(5) no
C13 C14 . . 1.386(5) no
C14 C15 . . 1.398(5) no
C15 C16 . . 1.390(4) no
C16 C17 . . 1.374(5) no
C1 H1B . . 0.9300 no
C2 H2C . . 0.9300 no
C3 H3A . . 0.9300 no
C4 H4A . . 0.9300 no
C5 H5A . . 0.9300 no
C8 H8A . . 0.9300 no
C13 H13A . . 0.9300 no
C17 H17A . . 0.9300 no
C19 H19A . . 0.9600 no
C19 H19B . . 0.9600 no
C19 H19C . . 0.9600 no
C20 H20A . . 0.9600 no
C20 H20B . . 0.9600 no
C20 H20C . . 0.9600 no
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
_geom_hbond_publ_flag
N2 H2A O2 1_565 0.86 2.27 3.101(4) 162 yes
N2 H2B N3 2_566 0.86 2.31 3.098(5) 152 yes
O3 H3B O1 . 0.82 2.19 2.654(4) 116 no
C1 H1B N1 . 0.93 2.47 2.790(5) 100 no
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
C19 O1 C14 C13 . . . . 27.2(7) no
C19 O1 C14 C15 . . . . -153.2(4) no
C20 O2 C16 C15 . . . . 163.1(3) no
C20 O2 C16 C17 . . . . -18.0(5) no
C11 N1 C7 C6 . . . . 178.0(3) no
C11 N1 C7 C8 . . . . -1.6(5) no
C7 N1 C11 N2 . . . . -177.7(3) no
C7 N1 C11 C10 . . . . 3.1(5) no
C6 C1 C2 C3 . . . . -0.1(6) no
C2 C1 C6 C5 . . . . -0.6(5) no
C2 C1 C6 C7 . . . . 178.7(3) no
C1 C2 C3 C4 . . . . 0.8(6) no
C2 C3 C4 C5 . . . . -1.0(6) no
C3 C4 C5 C6 . . . . 0.3(6) no
C4 C5 C6 C1 . . . . 0.5(6) no
C4 C5 C6 C7 . . . . -178.9(3) no
C1 C6 C7 N1 . . . . -15.1(5) no
C1 C6 C7 C8 . . . . 164.5(3) no
C5 C6 C7 N1 . . . . 164.2(3) no
C5 C6 C7 C8 . . . . -16.2(5) no
N1 C7 C8 C9 . . . . -0.3(5) no
C6 C7 C8 C9 . . . . -179.9(3) no
C7 C8 C9 C10 . . . . 0.8(5) no
C7 C8 C9 C12 . . . . -179.2(3) no
C8 C9 C10 C11 . . . . 0.7(4) no
C8 C9 C10 C18 . . . . -176.8(3) no
C12 C9 C10 C11 . . . . -179.4(3) no
C12 C9 C10 C18 . . . . 3.1(5) no
C8 C9 C12 C13 . . . . 42.3(5) no
C8 C9 C12 C17 . . . . -135.1(4) no
C10 C9 C12 C13 . . . . -137.6(4) no
C10 C9 C12 C17 . . . . 45.0(5) no
C9 C10 C11 N1 . . . . -2.6(5) no
C9 C10 C11 N2 . . . . 178.1(3) no
C18 C10 C11 N1 . . . . 175.0(3) no
C18 C10 C11 N2 . . . . -4.3(5) no
C9 C12 C13 C14 . . . . -177.6(4) no
C17 C12 C13 C14 . . . . -0.2(6) no
C9 C12 C17 C16 . . . . 177.9(3) no
C13 C12 C17 C16 . . . . 0.5(5) no
C12 C13 C14 O1 . . . . -179.1(4) no
C12 C13 C14 C15 . . . . 1.4(6) no
O1 C14 C15 O3 . . . . 0.4(5) no
O1 C14 C15 C16 . . . . 177.6(4) no
C13 C14 C15 O3 . . . . 179.9(4) no
C13 C14 C15 C16 . . . . -2.8(6) no
O3 C15 C16 O2 . . . . -0.8(5) no
O3 C15 C16 C17 . . . . -179.7(3) no
C14 C15 C16 O2 . . . . -177.9(3) no
C14 C15 C16 C17 . . . . 3.2(5) no
O2 C16 C17 C12 . . . . 179.2(3) no
C15 C16 C17 C12 . . . . -2.0(5) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29630263
