#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228649.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_2228649
loop_
_publ_author_name
'Ye, Yuan-Feng'
'Wang, Huai-Qing'
'Feng, Zhi-Qiang'
_publ_section_title
;
 2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile
;
_journal_coeditor_code           BQ2258
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o71
_journal_paper_doi               10.1107/S1600536810050609
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H13 Cl2 N3'
_chemical_formula_moiety         'C22 H13 Cl2 N3'
_chemical_formula_sum            'C22 H13 Cl2 N3'
_chemical_formula_weight         390.25
_chemical_name_systematic
;
2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile
;
_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                72.78(3)
_cell_angle_beta                 89.17(3)
_cell_angle_gamma                74.81(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5020(19)
_cell_length_b                   10.054(2)
_cell_length_c                   10.735(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     943.1(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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  'Entaf--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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3686
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0483
_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)+(0.0950P)²+] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                2648
_reflns_number_total             3463
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2258.cif
_cod_data_source_block           I
_cod_original_cell_volume        943.1(3)
_cod_database_code               2228649
_cod_database_fobs_code          2228649
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.37446(8) 0.08316(9) 0.92700(9) 0.0687(3) Uani d . 1 . .
N N1 0.36411(19) 0.4640(2) 0.89712(17) 0.0331(4) Uani d . 1 . .
C C1 -0.0992(3) 0.2943(3) 0.9925(3) 0.0425(6) Uani d . 1 . .
H H1B -0.0942 0.3531 1.0439 0.051 Uiso calc R 1 . .
Cl Cl2 0.13996(8) 0.12749(9) 0.73801(8) 0.0635(3) Uani d . 1 . .
N N2 0.4248(2) 0.3529(3) 1.1161(2) 0.0414(5) Uani d . 1 . .
H H2A 0.480(3) 0.408(3) 1.110(2) 0.044(7) Uiso d . 1 . .
H H2B 0.398(3) 0.313(3) 1.193(3) 0.053(8) Uiso d . 1 . .
C C2 -0.2176(3) 0.2375(3) 0.9987(3) 0.0477(6) Uani d . 1 . .
H H2C -0.2919 0.2580 1.0532 0.057 Uiso calc R 1 . .
C C3 -0.2235(3) 0.1508(3) 0.9234(3) 0.0442(6) Uani d . 1 . .
N N3 0.1702(3) 0.1711(3) 1.2494(2) 0.0542(6) Uani d . 1 . .
C C4 -0.1143(3) 0.1165(3) 0.8436(2) 0.0426(6) Uani d . 1 . .
H H4A -0.1192 0.0557 0.7942 0.051 Uiso calc R 1 . .
C C5 0.0034(3) 0.1752(3) 0.8384(2) 0.0390(6) Uani d . 1 . .
C C6 0.0130(2) 0.2659(2) 0.9114(2) 0.0350(5) Uani d . 1 . .
C C7 0.1356(2) 0.3340(2) 0.9053(2) 0.0347(5) Uani d . 1 . .
C C8 0.1657(3) 0.4256(3) 0.7898(2) 0.0394(6) Uani d . 1 . .
H H8A 0.1114 0.4431 0.7125 0.047 Uiso calc R 1 . .
C C9 0.2771(2) 0.4911(2) 0.7898(2) 0.0353(5) Uani d . 1 . .
C C10 0.3364(2) 0.3766(2) 1.0103(2) 0.0315(5) Uani d . 1 . .
C C11 0.2194(2) 0.3119(2) 1.0184(2) 0.0327(5) Uani d . 1 . .
C C12 0.1897(2) 0.2309(3) 1.1454(2) 0.0372(5) Uani d . 1 . .
C C13 0.3005(2) 0.6054(3) 0.6730(2) 0.0364(5) Uani d . 1 . .
C C14 0.1836(3) 0.7200(3) 0.6165(3) 0.0528(7) Uani d . 1 . .
H H14A 0.0907 0.7181 0.6441 0.063 Uiso calc R 1 . .
C C15 0.2017(4) 0.8417(3) 0.5168(3) 0.0660(9) Uani d . 1 . .
H H15A 0.1209 0.9184 0.4783 0.079 Uiso calc R 1 . .
C C16 0.3370(3) 0.8461(3) 0.4774(3) 0.0615(8) Uani d . 1 . .
H H16A 0.3486 0.9278 0.4140 0.074 Uiso calc R 1 . .
C C17 0.4602(3) 0.7293(3) 0.5308(2) 0.0459(6) Uani d . 1 . .
C C18 0.6025(3) 0.7317(4) 0.4896(3) 0.0615(8) Uani d . 1 . .
H H18A 0.6156 0.8140 0.4280 0.074 Uiso calc R 1 . .
C C19 0.7199(3) 0.6162(4) 0.5385(3) 0.0623(8) Uani d . 1 . .
H H19A 0.8128 0.6208 0.5126 0.075 Uiso calc R 1 . .
C C20 0.7004(3) 0.4907(3) 0.6275(3) 0.0520(7) Uani d . 1 . .
H H20A 0.7801 0.4101 0.6576 0.062 Uiso calc R 1 . .
C C21 0.5663(3) 0.4846(3) 0.6708(2) 0.0411(6) Uani d . 1 . .
H H21A 0.5561 0.3999 0.7306 0.049 Uiso calc R 1 . .
C C22 0.4431(3) 0.6037(3) 0.6270(2) 0.0355(5) Uani d . 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'
Cl Cl 0.1484 0.1585 '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
C10 N1 C9 . . 118.57(19) ?
C2 C1 C6 . . 121.8(2) ?
C2 C1 H1B . . 119.1 ?
C6 C1 H1B . . 119.1 ?
C10 N2 H2A . . 117.4(17) ?
C10 N2 H2B . . 118.6(19) ?
H2A N2 H2B . . 118(2) ?
C3 C2 C1 . . 118.7(2) ?
C3 C2 H2C . . 120.7 ?
C1 C2 H2C . . 120.7 ?
C2 C3 C4 . . 122.0(2) ?
C2 C3 Cl1 . . 119.0(2) ?
C4 C3 Cl1 . . 118.96(19) ?
C3 C4 C5 . . 118.3(2) ?
C3 C4 H4A . . 120.8 ?
C5 C4 H4A . . 120.8 ?
C6 C5 C4 . . 121.7(2) ?
C6 C5 Cl2 . . 121.38(17) ?
C4 C5 Cl2 . . 116.88(19) ?
C5 C6 C1 . . 117.4(2) ?
C5 C6 C7 . . 123.1(2) ?
C1 C6 C7 . . 119.5(2) ?
C8 C7 C11 . . 118.0(2) ?
C8 C7 C6 . . 121.8(2) ?
C11 C7 C6 . . 120.2(2) ?
C9 C8 C7 . . 119.8(2) ?
C9 C8 H8A . . 120.1 ?
C7 C8 H8A . . 120.1 ?
N1 C9 C8 . . 122.7(2) ?
N1 C9 C13 . . 115.38(19) ?
C8 C9 C13 . . 121.8(2) ?
N1 C10 N2 . . 117.0(2) ?
N1 C10 C11 . . 121.53(19) ?
N2 C10 C11 . . 121.4(2) ?
C7 C11 C10 . . 119.3(2) ?
C7 C11 C12 . . 123.0(2) ?
C10 C11 C12 . . 117.6(2) ?
N3 C12 C11 . . 175.9(3) ?
C14 C13 C22 . . 120.1(2) ?
C14 C13 C9 . . 118.0(2) ?
C22 C13 C9 . . 121.7(2) ?
C13 C14 C15 . . 121.0(3) ?
C13 C14 H14A . . 119.5 ?
C15 C14 H14A . . 119.5 ?
C16 C15 C14 . . 119.8(3) ?
C16 C15 H15A . . 120.1 ?
C14 C15 H15A . . 120.1 ?
C15 C16 C17 . . 121.2(3) ?
C15 C16 H16A . . 119.4 ?
C17 C16 H16A . . 119.4 ?
C16 C17 C18 . . 121.9(3) ?
C16 C17 C22 . . 119.7(2) ?
C18 C17 C22 . . 118.4(2) ?
C19 C18 C17 . . 121.3(3) ?
C19 C18 H18A . . 119.3 ?
C17 C18 H18A . . 119.3 ?
C18 C19 C20 . . 119.6(3) ?
C18 C19 H19A . . 120.2 ?
C20 C19 H19A . . 120.2 ?
C21 C20 C19 . . 120.8(3) ?
C21 C20 H20A . . 119.6 ?
C19 C20 H20A . . 119.6 ?
C20 C21 C22 . . 121.4(2) ?
C20 C21 H21A . . 119.3 ?
C22 C21 H21A . . 119.3 ?
C21 C22 C17 . . 118.2(2) ?
C21 C22 C13 . . 123.8(2) ?
C17 C22 C13 . . 118.0(2) ?
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
Cl1 C3 . 1.736(2) ?
N1 C10 . 1.341(3) ?
N1 C9 . 1.345(3) ?
C1 C2 . 1.382(3) ?
C1 C6 . 1.392(3) ?
C1 H1B . 0.9300 ?
Cl2 C5 . 1.736(2) ?
N2 C10 . 1.347(3) ?
N2 H2A . 0.84(3) ?
N2 H2B . 0.86(3) ?
C2 C3 . 1.365(4) ?
C2 H2C . 0.9300 ?
C3 C4 . 1.376(3) ?
N3 C12 . 1.139(3) ?
C4 C5 . 1.388(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.387(3) ?
C6 C7 . 1.490(3) ?
C7 C8 . 1.386(3) ?
C7 C11 . 1.390(3) ?
C8 C9 . 1.384(3) ?
C8 H8A . 0.9300 ?
C9 C13 . 1.488(3) ?
C10 C11 . 1.417(3) ?
C11 C12 . 1.434(3) ?
C13 C14 . 1.365(4) ?
C13 C22 . 1.432(3) ?
C14 C15 . 1.414(4) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.356(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.406(4) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.421(4) ?
C17 C22 . 1.421(3) ?
C18 C19 . 1.358(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.394(4) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.360(4) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.405(3) ?
C21 H21A . 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
_geom_hbond_publ_flag
N2 H2A N1 2_667 0.85(3) 2.19(3) 3.034(3) 176(2) yes
C4 H4A N3 2_557 0.93 2.62 3.488(4) 155 yes
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
C6 C1 C2 C3 . . . . 0.3(4) ?
C1 C2 C3 C4 . . . . 1.1(4) ?
C1 C2 C3 Cl1 . . . . -178.1(2) ?
C2 C3 C4 C5 . . . . -1.3(4) ?
Cl1 C3 C4 C5 . . . . 177.91(18) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C3 C4 C5 Cl2 . . . . 179.22(19) ?
C4 C5 C6 C1 . . . . 1.2(4) ?
Cl2 C5 C6 C1 . . . . -177.86(18) ?
C4 C5 C6 C7 . . . . -178.2(2) ?
Cl2 C5 C6 C7 . . . . 2.7(3) ?
C2 C1 C6 C5 . . . . -1.4(4) ?
C2 C1 C6 C7 . . . . 178.0(2) ?
C5 C6 C7 C8 . . . . 59.9(3) ?
C1 C6 C7 C8 . . . . -119.5(3) ?
C5 C6 C7 C11 . . . . -123.1(3) ?
C1 C6 C7 C11 . . . . 57.5(3) ?
C11 C7 C8 C9 . . . . 0.3(4) ?
C6 C7 C8 C9 . . . . 177.4(2) ?
C10 N1 C9 C8 . . . . -4.0(3) ?
C10 N1 C9 C13 . . . . 171.27(19) ?
C7 C8 C9 N1 . . . . 3.5(4) ?
C7 C8 C9 C13 . . . . -171.4(2) ?
C9 N1 C10 N2 . . . . -179.4(2) ?
C9 N1 C10 C11 . . . . 0.7(3) ?
C8 C7 C11 C10 . . . . -3.4(3) ?
C6 C7 C11 C10 . . . . 179.4(2) ?
C8 C7 C11 C12 . . . . 173.9(2) ?
C6 C7 C11 C12 . . . . -3.3(3) ?
N1 C10 C11 C7 . . . . 3.1(3) ?
N2 C10 C11 C7 . . . . -176.9(2) ?
N1 C10 C11 C12 . . . . -174.4(2) ?
N2 C10 C11 C12 . . . . 5.6(3) ?
C7 C11 C12 N3 . . . . -155(4) ?
C10 C11 C12 N3 . . . . 22(4) ?
N1 C9 C13 C14 . . . . -123.8(2) ?
C8 C9 C13 C14 . . . . 51.5(3) ?
N1 C9 C13 C22 . . . . 50.6(3) ?
C8 C9 C13 C22 . . . . -134.1(2) ?
C22 C13 C14 C15 . . . . -3.2(4) ?
C9 C13 C14 C15 . . . . 171.4(3) ?
C13 C14 C15 C16 . . . . -0.9(5) ?
C14 C15 C16 C17 . . . . 2.3(5) ?
C15 C16 C17 C18 . . . . 179.4(3) ?
C15 C16 C17 C22 . . . . 0.4(5) ?
C16 C17 C18 C19 . . . . -177.6(3) ?
C22 C17 C18 C19 . . . . 1.3(4) ?
C17 C18 C19 C20 . . . . 2.2(5) ?
C18 C19 C20 C21 . . . . -3.1(4) ?
C19 C20 C21 C22 . . . . 0.4(4) ?
C20 C21 C22 C17 . . . . 3.1(4) ?
C20 C21 C22 C13 . . . . -177.5(2) ?
C16 C17 C22 C21 . . . . 175.1(2) ?
C18 C17 C22 C21 . . . . -3.9(4) ?
C16 C17 C22 C13 . . . . -4.4(4) ?
C18 C17 C22 C13 . . . . 176.7(2) ?
C14 C13 C22 C21 . . . . -173.7(2) ?
C9 C13 C22 C21 . . . . 12.0(3) ?
C14 C13 C22 C17 . . . . 5.7(3) ?
C9 C13 C22 C17 . . . . -168.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656407
