#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/64/2016489.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_2016489
loop_
_publ_author_name
'Janczak, Jan'
_publ_section_title
;
 Wave-like structure in
 3-(4,6-diamino-1,3,5-triazin-2-yl)-2-naphthonitrile
;
_journal_coeditor_code           GD3192
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o159
_journal_page_last               o161
_journal_paper_doi               10.1107/S0108270108003831
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 N6'
_chemical_formula_moiety         'C14 H10 N6'
_chemical_formula_sum            'C14 H10 N6'
_chemical_formula_weight         262.28
_chemical_name_systematic
;
3-(4,6-diamino-1,3,5-triazin-2-yl)-2-naphthonitrile
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   35.798(7)
_cell_length_b                   7.3190(10)
_cell_length_c                   21.459(4)
_cell_measurement_reflns_used    1203
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.86
_cell_volume                     4919(2)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Kuma KM-4 with CCD area-detector'
_diffrn_measurement_method       ω-scan
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0927
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27666
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'face-indexed (SHELXTL; Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      1.41
_exptl_crystal_density_method    flotation
_exptl_crystal_description       paralellepiped
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.242
_refine_ls_extinction_coef       0.000643(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0055P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0714
_reflns_number_gt                3357
_reflns_number_total             5875
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3192.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2016489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N N1 0.24088(5) -0.0920(2) 0.36585(8) 0.0428(4) Uani d . 1
N N2 0.16587(5) -0.0631(3) 0.32362(8) 0.0436(4) Uani d . 1
N N3 0.19370(4) -0.0352(2) 0.24293(7) 0.0409(4) Uani d . 1
N N4 0.21289(5) -0.1033(3) 0.44220(8) 0.0545(5) Uani d . 1
H H4A 0.1916 -0.0994 0.4505 0.065 Uiso calc R 1
H H4B 0.2384 -0.1183 0.4768 0.065 Uiso calc R 1
N N5 0.12212(5) -0.0133(3) 0.20440(8) 0.0590(6) Uani d . 1
H H5A 0.1005 -0.0139 0.2118 0.071 Uiso calc R 1
H H5B 0.1183 0.0032 0.1620 0.071 Uiso calc R 1
N N6 0.33079(7) 0.1134(4) 0.46499(10) 0.0747(7) Uani d . 1
C C1 0.34280(6) 0.0222(3) 0.32101(12) 0.0554(6) Uani d . 1
H H1 0.3696 0.0619 0.3557 0.066 Uiso calc R 1
C C2 0.31020(6) 0.0096(3) 0.33764(10) 0.0433(5) Uani d . 1
C C3 0.26894(5) -0.0503(3) 0.28489(9) 0.0384(4) Uani d . 1
C C4 0.26267(6) -0.0921(3) 0.21832(10) 0.0449(5) Uani d . 1
H H4 0.2357 -0.1300 0.1837 0.054 Uiso calc R 1
C C5 0.29570(7) -0.0799(3) 0.20034(11) 0.0514(6) Uani d . 1
C C6 0.28874(9) -0.1225(4) 0.13115(13) 0.0526(7) Uani d . 1
H H6 0.2617 -0.1571 0.0958 0.065 Uiso calc R 1
C C7 0.32178(13) -0.1126(5) 0.11631(19) 0.0641(11) Uani d . 1
H H7 0.3172 -0.1410 0.0709 0.089 Uiso calc R 1
C C8 0.36263(12) -0.0600(5) 0.1694(2) 0.0779(12) Uani d . 1
H H8 0.3850 -0.0552 0.1589 0.101 Uiso calc R 1
C C9 0.36997(9) -0.0161(5) 0.23543(18) 0.0669(10) Uani d . 1
H H9 0.3973 0.0193 0.2697 0.083 Uiso calc R 1
C C10 0.33665(7) -0.0233(3) 0.25343(13) 0.0567(6) Uani d . 1
C C11 0.31975(6) 0.0652(3) 0.40836(11) 0.0512(6) Uani d . 1
C C12 0.23228(5) -0.0616(3) 0.29931(9) 0.0378(4) Uani d . 1
C C13 0.20624(6) -0.0861(3) 0.37555(9) 0.0412(5) Uani d . 1
C C14 0.16155(5) -0.0379(3) 0.25874(9) 0.0416(5) Uani d . 1
N N21 0.06563(5) 0.0934(3) 0.42305(7) 0.0420(4) Uani d . 1
N N22 0.13485(4) -0.0428(2) 0.47121(7) 0.0408(4) Uani d . 1
N N23 0.10629(4) 0.0448(2) 0.54784(7) 0.0393(4) Uani d . 1
N N24 0.09287(5) 0.0056(3) 0.35111(8) 0.0593(6) Uani d . 1
H H24A 0.1127 -0.0414 0.3444 0.071 Uiso calc R 1
H H24B 0.0696 0.0440 0.3154 0.071 Uiso calc R 1
N N25 0.17220(5) -0.0912(3) 0.59144(8) 0.0514(5) Uani d . 1
H H25A 0.1922 -0.1397 0.5857 0.062 Uiso calc R 1
H H25B 0.1748 -0.0839 0.6334 0.062 Uiso calc R 1
N N26 -0.03217(6) 0.1319(4) 0.30228(9) 0.0725(7) Uani d . 1
C C21 -0.03870(6) 0.2784(3) 0.44141(10) 0.0434(5) Uani d . 1
H H21 -0.0648 0.2985 0.4008 0.052 Uiso calc R 1
C C22 -0.00531(5) 0.2085(3) 0.43414(9) 0.0387(4) Uani d . 1
C C23 0.03541(5) 0.1792(3) 0.49551(9) 0.0364(4) Uani d . 1
C C24 0.03951(6) 0.2220(3) 0.56061(9) 0.0429(5) Uani d . 1
H H24 0.0660 0.2056 0.6009 0.052 Uiso calc R 1
C C25 0.00547(6) 0.2899(3) 0.56967(9) 0.0421(5) Uani d . 1
C C26 0.00936(7) 0.3294(4) 0.63708(11) 0.0601(7) Uani d . 1
H H26 0.0353 0.3103 0.6782 0.072 Uiso calc R 1
C C27 -0.02471(8) 0.3955(4) 0.64224(13) 0.0709(8) Uani d . 1
H H27 -0.0217 0.4209 0.6869 0.085 Uiso calc R 1
C C28 -0.06406(7) 0.4255(4) 0.58130(13) 0.0627(7) Uani d . 1
H H28 -0.0869 0.4713 0.5857 0.075 Uiso calc R 1
C C29 -0.06891(7) 0.3884(3) 0.51653(12) 0.0521(6) Uani d . 1
H H29 -0.0953 0.4080 0.4764 0.062 Uiso calc R 1
C C210 -0.03451(6) 0.3201(3) 0.50836(10) 0.0407(5) Uani d . 1
C C211 -0.01620(6) 0.1632(3) 0.36179(10) 0.0492(5) Uani d . 1
C C212 0.07168(5) 0.1017(3) 0.48856(9) 0.0360(4) Uani d . 1
C C213 0.09817(5) 0.0186(3) 0.41668(9) 0.0404(5) Uani d . 1
C C214 0.13691(5) -0.0271(3) 0.53504(9) 0.0387(4) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C12 N1 C13 114.13(15) y
C14 N2 C13 114.67(15) y
C12 N3 C14 113.74(15) y
C13 N4 H4A 120.0 ?
C13 N4 H4B 120.0 ?
H4A N4 H4B 120.0 ?
C14 N5 H5A 120.0 ?
C14 N5 H5B 120.0 ?
H5A N5 H5B 120.0 ?
C2 C1 C10 121.7(2) ?
C2 C1 H1 119.2 ?
C10 C1 H1 119.2 ?
C1 C2 C3 119.68(18) ?
C1 C2 C11 117.03(19) ?
C3 C2 C11 123.26(16) ?
C4 C3 C2 118.72(16) ?
C4 C3 C12 119.29(17) ?
C2 C3 C12 121.95(16) ?
C3 C4 C5 122.35(19) ?
C3 C4 H4 118.8 ?
C5 C4 H4 118.8 ?
C4 C5 C10 118.41(19) ?
C4 C5 C6 121.8(2) ?
C10 C5 C6 119.8(2) ?
C7 C6 C5 120.0(3) ?
C7 C6 H6 120.0 ?
C5 C6 H6 120.0 ?
C6 C7 C8 120.2(3) ?
C6 C7 H7 119.9 ?
C8 C7 H7 119.9 ?
C9 C8 C7 120.9(2) ?
C9 C8 H8 119.5 ?
C7 C8 H8 119.5 ?
C8 C9 C10 121.0(3) ?
C8 C9 H9 119.5 ?
C10 C9 H9 119.5 ?
C1 C10 C5 119.13(18) ?
C1 C10 C9 122.8(2) ?
C5 C10 C9 118.0(2) ?
N6 C11 C2 173.9(2) y
N1 C12 N3 126.72(16) y
N1 C12 C3 117.74(16) ?
N3 C12 C3 115.52(15) ?
N4 C13 N2 117.57(16) ?
N4 C13 N1 117.39(16) ?
N2 C13 N1 125.04(16) y
N2 C14 N5 117.86(16) ?
N2 C14 N3 125.60(16) y
N5 C14 N3 116.54(16) ?
C212 N21 C213 115.00(15) y
C214 N22 C213 114.09(15) y
C212 N23 C214 113.13(14) y
C213 N24 H24A 120.0 ?
C213 N24 H24B 120.0 ?
H24A N24 H24B 120.0 ?
C214 N25 H25A 120.0 ?
C214 N25 H25B 120.0 ?
H25A N25 H25B 120.0 ?
C22 C21 C210 121.92(17) ?
C22 C21 H21 119.0 ?
C210 C21 H21 119.0 ?
C21 C22 C23 120.29(16) ?
C21 C22 C211 114.23(16) ?
C23 C22 C211 125.43(16) ?
C24 C23 C22 117.62(16) ?
C24 C23 C212 121.48(16) ?
C22 C23 C212 120.90(15) ?
C23 C24 C25 123.21(17) ?
C23 C24 H24 118.4 ?
C25 C24 H24 118.4 ?
C24 C25 C26 123.25(18) ?
C24 C25 C210 118.50(16) ?
C26 C25 C210 118.25(18) ?
C27 C26 C25 120.4(2) ?
C27 C26 H26 119.8 ?
C25 C26 H26 119.8 ?
C26 C27 C28 120.9(2) ?
C26 C27 H27 119.5 ?
C28 C27 H27 119.5 ?
C29 C28 C27 120.2(2) ?
C29 C28 H28 119.9 ?
C27 C28 H28 119.9 ?
C28 C29 C210 121.0(2) ?
C28 C29 H29 119.5 ?
C210 C29 H29 119.5 ?
C21 C210 C25 118.43(16) ?
C21 C210 C29 122.37(18) ?
C25 C210 C29 119.19(17) ?
N26 C211 C22 167.7(2) y
N21 C212 N23 126.70(16) y
N21 C212 C23 115.11(15) ?
N23 C212 C23 118.18(15) ?
N24 C213 N22 118.44(16) ?
N24 C213 N21 116.61(16) ?
N22 C213 N21 124.95(15) y
N22 C214 N25 116.99(16) ?
N22 C214 N23 126.13(16) y
N25 C214 N23 116.87(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C12 1.325(2) ?
N1 C13 1.352(2) ?
N2 C14 1.337(2) ?
N2 C13 1.340(2) ?
N3 C12 1.337(2) ?
N3 C14 1.347(2) ?
N4 C13 1.337(2) ?
N4 H4A 0.8600 ?
N4 H4B 0.8600 ?
N5 C14 1.337(2) ?
N5 H5A 0.8600 ?
N5 H5B 0.8600 ?
N6 C11 1.136(3) y
C1 C2 1.378(2) ?
C1 C10 1.397(3) ?
C1 H1 0.9300 ?
C2 C3 1.425(3) y
C2 C11 1.443(3) y
C3 C4 1.369(3) ?
C3 C12 1.488(2) y
C4 C5 1.412(3) ?
C4 H4 0.9300 ?
C5 C10 1.413(3) ?
C5 C6 1.415(3) ?
C6 C7 1.366(4) ?
C6 H6 0.9300 ?
C7 C8 1.402(5) ?
C7 H7 0.9300 ?
C8 C9 1.349(4) ?
C8 H8 0.9300 ?
C9 C10 1.420(3) ?
C9 H9 0.9300 ?
N21 C212 1.316(2) ?
N21 C213 1.351(2) ?
N22 C214 1.340(2) ?
N22 C213 1.343(2) ?
N23 C212 1.341(2) ?
N23 C214 1.357(2) ?
N24 C213 1.329(2) ?
N24 H24A 0.8600 ?
N24 H24B 0.8600 ?
N25 C214 1.340(2) ?
N25 H25A 0.8600 ?
N25 H25B 0.8600 ?
N26 C211 1.141(2) y
C21 C22 1.375(2) ?
C21 C210 1.404(2) ?
C21 H21 0.9300 ?
C22 C23 1.429(2) ?
C22 C211 1.444(2) y
C23 C24 1.368(2) ?
C23 C212 1.488(2) y
C24 C25 1.412(3) ?
C24 H24 0.9300 ?
C25 C26 1.414(2) ?
C25 C210 1.414(3) ?
C26 C27 1.364(3) ?
C26 H26 0.9300 ?
C27 C28 1.398(3) ?
C27 H27 0.9300 ?
C28 C29 1.342(3) ?
C28 H28 0.9300 ?
C29 C210 1.415(3) ?
C29 H29 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
N4 H4A N22 . 0.86 2.32 3.171(2) 172 y
N5 H5B N23 6 0.86 2.30 3.132(2) 163 y
N24 H24A N2 . 0.86 2.16 2.984(2) 161 y
N24 H24B N26 2 0.86 2.30 3.078(3) 150 y
N25 H25B N3 6_556 0.86 2.28 3.096(2) 158 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726186
