##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C22 H13 Cl2 N3'
_chemical_formula_sum     'C22 H13 Cl2 N3'
_chemical_formula_iupac     'C22 H13 Cl2 N3'
_chemical_formula_weight     390.25
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.5020(19)
_cell_length_b     10.054(2)
_cell_length_c     10.735(2)
_cell_angle_alpha     72.78(3)
_cell_angle_beta     89.17(3)
_cell_angle_gamma     74.81(3)
_cell_volume     943.1(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     14
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.374
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     400
_exptl_absorpt_coefficient_mu     0.355
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.9009
_exptl_absorpt_correction_T_max     0.9653
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Entaf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3686
_diffrn_reflns_av_R_equivalents     0.0140
_diffrn_reflns_av_sigmaI/netI     0.0349
_diffrn_reflns_theta_min     1.99
_diffrn_reflns_theta_max     25.37
_diffrn_reflns_theta_full     25.37
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     2
_diffrn_standards_decay_%     1
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3463
_reflns_number_gt     2648
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0675
_refine_ls_R_factor_gt     0.0483
_refine_ls_wR_factor_gt     0.1304
_refine_ls_wR_factor_ref     0.1455
_refine_ls_goodness_of_fit_ref     1.003
_refine_ls_restrained_S_all     1.003
_refine_ls_number_reflns     3463
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w=1/[σ²(Fo²)+(0.0950P)²+] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.179
_refine_diff_density_min     -0.365
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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_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_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_
    _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
data_global
_journal_date_recd_electronic     2010-11-24
_journal_date_accepted     2010-12-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      1
_journal_page_first     o71
_journal_page_last     o71
_journal_paper_category     QO
_journal_coeditor_code     BQ2258
_publ_contact_author_name     'Professor 'Yuan-Feng Ye'
_publ_contact_author_address
;
'Yuan-Feng Ye'
School of Material Engineering
Jinling Institute of Technology
Nanjing 211169
People's Republic of China
;
_publ_contact_author_email     'dalantom@126.com'
_publ_section_title
;
2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'Yuan-Feng Ye'
;
School of Material Engineering
Jinling Institute of Technology
Nanjing 211169
People's Republic of China
;
    'Huai-Qing Wang'
;
School of Material Engineering
Jinling Institute of Technology
Nanjing 211169
People's Republic of China
;
    'Zhi-Qiang Feng'
;
School of Material Engineering
Jinling Institute of Technology
Nanjing 211169
People's Republic of China
;
