#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/34/2013488.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_2013488
loop_
_publ_author_name
'Bruno, Giuseppe'
'Nicoló, Francesco'
'Puntoriero, Fausto'
'Giuffrida, Gaetano'
'Ricevuto, Vittorio'
'Rosace, Giuseppe'
_publ_section_title
4-[4-(Dimethylamino)benzylideneamino]-3,5-bis(2-pyridyl)-4H-1,2,4-triazole
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o390
_journal_page_last               o391
_journal_paper_doi               10.1107/S0108270103011697
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C21 H19 N7'
_chemical_formula_moiety         'C21 H19 N7'
_chemical_formula_sum            'C21 H19 N7'
_chemical_formula_weight         369.43
_chemical_name_systematic
;
(4-Dimethylamino-benzylidene)-(3,5-bis(2-Pyridyl)-1,2,4-triazol-4-yl)amine
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 117.690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.300(4)
_cell_length_b                   9.469(2)
_cell_length_c                   17.440(2)
_cell_measurement_reflns_used    31
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13.59
_cell_measurement_theta_min      6.25
_cell_volume                     3845.8(11)
_computing_cell_refinement       'P3/V '
_computing_data_collection       'P3/V  (Siemens, 1989)'
_computing_data_reduction        'SHELXTL-Plus (Siemens, 1990)'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'PARST97 (Nardelli, 1995) and SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR93 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0102
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4041
_diffrn_reflns_theta_full        0.5
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       'regular prism'
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.142
_refine_ls_extinction_coef       0.00110(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.793
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                2023
_reflns_number_total             3413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1615.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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3846.0(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013488
_cod_database_fobs_code          2013488
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_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
_atom_site_type_symbol
N1 0.08976(5) 1.06093(13) 0.29330(7) 0.0398(3) Uani d . 1 . . N
C1 0.05795(6) 1.02098(16) 0.20868(8) 0.0390(4) Uani d . 1 A . C
N2 0.03231(5) 1.13247(13) 0.16159(7) 0.0457(3) Uani d . 1 . . N
N3 0.04866(5) 1.24847(13) 0.21599(8) 0.0466(3) Uani d . 1 . . N
C2 0.08303(6) 1.20330(16) 0.29491(9) 0.0409(4) Uani d . 1 . . C
C3 0.11035(6) 1.29603(16) 0.37146(9) 0.0436(4) Uani d . 1 . . C
N4 0.16527(6) 1.26995(15) 0.42673(8) 0.0613(4) Uani d . 1 . . N
C4 0.19010(8) 1.3577(2) 0.49395(12) 0.0782(6) Uani d . 1 . . C
H4 0.2284 1.3417 0.5333 0.094 Uiso calc R 1 . . H
C5 0.16306(10) 1.4694(2) 0.50869(13) 0.0835(6) Uani d . 1 . . C
H5 0.1823 1.5271 0.5569 0.1 Uiso calc R 1 . . H
C6 0.10693(9) 1.4945(2) 0.45090(13) 0.0772(6) Uani d . 1 . . C
H6 0.0874 1.5703 0.4589 0.093 Uiso calc R 1 . . H
C7 0.07972(7) 1.40657(17) 0.38097(11) 0.0576(5) Uani d . 1 . . C
H7 0.0415 1.4212 0.3409 0.069 Uiso calc R 1 . . H
C8 0.05264(6) 0.87696(16) 0.17417(9) 0.0414(4) Uani d . 1 . . C
C9 0.03719(6) 0.86539(16) 0.08822(9) 0.0524(5) Uani d P 0.509(14) A 1 C
H9 0.0291 0.945 0.0533 0.063 Uiso calc PR 0.509(14) A 1 H
N9 0.03719(6) 0.86539(16) 0.08822(9) 0.0524(5) Uani d P 0.491(14) A 2 N
C10 0.03394(8) 0.7339(2) 0.05535(11) 0.0671(5) Uani d . 1 . . C
H10 0.0236 0.7236 -0.0031 0.08 Uiso calc R 1 A 1 H
C11 0.04547(8) 0.6165(2) 0.10588(12) 0.0709(5) Uani d . 1 A . C
H11 0.0438 0.527 0.0829 0.085 Uiso calc R 1 . . H
C12 0.05956(8) 0.6335(2) 0.19098(12) 0.0734(5) Uani d . 1 . . C
H12 0.0668 0.554 0.2258 0.088 Uiso calc R 1 A 1 H
N13 0.06339(7) 0.76390(17) 0.22676(9) 0.0611(5) Uani d P 0.509(14) A 1 N
C13 0.06339(7) 0.76390(17) 0.22676(9) 0.0611(5) Uani d P 0.491(14) A 2 C
H13 0.073 0.7744 0.2849 0.073 Uiso calc PR 0.491(14) A 2 H
N5 0.12722(5) 0.97417(13) 0.36358(7) 0.0464(3) Uani d . 1 . . N
C14 0.11254(6) 0.96846(16) 0.42368(9) 0.0440(4) Uani d . 1 . . C
H14 0.0786 1.0117 0.4153 0.053 Uiso calc R 1 . . H
C15 0.14722(6) 0.89665(16) 0.50438(8) 0.0409(4) Uani d . 1 . . C
C16 0.12409(6) 0.85994(17) 0.55869(9) 0.0481(4) Uani d . 1 . . C
H16 0.0862 0.8838 0.5427 0.058 Uiso calc R 1 . . H
C17 0.15525(7) 0.78974(17) 0.63513(9) 0.0496(4) Uani d . 1 . . C
H17 0.1379 0.7647 0.669 0.059 Uiso calc R 1 . . H
C18 0.21295(6) 0.75525(16) 0.66298(9) 0.0442(4) Uani d . 1 . . C
C19 0.23708(6) 0.79526(17) 0.60926(9) 0.0490(4) Uani d . 1 . . C
H19 0.2755 0.7757 0.6263 0.059 Uiso calc R 1 . . H
C20 0.20466(6) 0.86270(16) 0.53208(9) 0.0465(4) Uani d . 1 . . C
H20 0.2215 0.8864 0.4973 0.056 Uiso calc R 1 . . H
N6 0.24416(6) 0.68529(17) 0.73904(8) 0.0641(4) Uani d . 1 . . N
C21 0.21881(9) 0.6491(3) 0.79370(12) 0.1007(8) Uani d . 1 . . C
H21A 0.2466 0.6006 0.8442 0.151 Uiso calc R 1 . . H
H21B 0.1862 0.589 0.7625 0.151 Uiso calc R 1 . . H
H21C 0.2067 0.7337 0.811 0.151 Uiso calc R 1 . . H
C22 0.30393(8) 0.6556(3) 0.76989(13) 0.0988(8) Uani d . 1 . . C
H22A 0.3185 0.606 0.824 0.148 Uiso calc R 1 . . H
H22B 0.3246 0.7426 0.7781 0.148 Uiso calc R 1 . . H
H22C 0.3087 0.5984 0.7283 0.148 Uiso calc R 1 . . H
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 0 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-7 -1 7
9 -1 1
4 4 0
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
C2 N1 C1 106.00(10) yes
C2 N1 N5 126.80(10) yes
C1 N1 N5 126.90(10) yes
N2 C1 N1 109.30(10) yes
N2 C1 C8 124.42(12) ?
N1 C1 C8 126.27(13) ?
C1 N2 N3 107.70(10) yes
C2 N3 N2 107.60(10) yes
N3 C2 N1 109.40(10) yes
N3 C2 C3 124.11(14) ?
N1 C2 C3 126.46(13) ?
N4 C3 C7 123.42(14) ?
N4 C3 C2 116.86(14) ?
C7 C3 C2 119.67(14) ?
C4 N4 C3 116.29(15) ?
N4 C4 C5 124.29(19) ?
N4 C4 H4 117.9 ?
C5 C4 H4 117.9 ?
C4 C5 C6 118.34(18) ?
C4 C5 H5 120.8 ?
C6 C5 H5 120.8 ?
C5 C6 C7 119.25(18) ?
C5 C6 H6 120.4 ?
C7 C6 H6 120.4 ?
C6 C7 C3 118.41(16) ?
C6 C7 H7 120.8 ?
C3 C7 H7 120.8 ?
N13 C8 C9 122.97(15) ?
N13 C8 C1 120.44(13) ?
C9 C8 C1 116.59(13) ?
C10 C9 C8 117.80(15) ?
C10 C9 H9 121.1 ?
C8 C9 H9 121.1 ?
C9 C10 C11 121.60(16) ?
C9 C10 H10 119.2 ?
C11 C10 H10 119.2 ?
C10 C11 C12 118.34(17) ?
C10 C11 H11 120.8 ?
C12 C11 H11 120.8 ?
C11 C12 N13 121.99(17) ?
C11 C12 H12 119 ?
N13 C12 H12 119 ?
C8 N13 C12 117.27(14) ?
C14 N5 N1 112.30(10) yes
N5 C14 C15 121.70(10) yes
N5 C14 H14 119.1 ?
C15 C14 H14 119.1 ?
C16 C15 C20 117.03(13) ?
C16 C15 C14 120.35(13) ?
C20 C15 C14 122.61(14) ?
C17 C16 C15 122.19(14) ?
C17 C16 H16 118.9 ?
C15 C16 H16 118.9 ?
C16 C17 C18 120.84(14) ?
C16 C17 H17 119.6 ?
C18 C17 H17 119.6 ?
N6 C18 C17 121.07(14) ?
N6 C18 C19 121.67(14) ?
C17 C18 C19 117.26(13) ?
C20 C19 C18 120.83(14) ?
C20 C19 H19 119.6 ?
C18 C19 H19 119.6 ?
C19 C20 C15 121.82(14) ?
C19 C20 H20 119.1 ?
C15 C20 H20 119.1 ?
C18 N6 C22 121.31(15) ?
C18 N6 C21 120.42(15) ?
C22 N6 C21 118.09(14) ?
N6 C21 H21A 109.5 ?
N6 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
N6 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
N6 C22 H22A 109.5 ?
N6 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
N6 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
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 C2 . 1.362(2) yes
N1 C1 . 1.369(2) yes
N1 N5 . 1.4230(10) yes
C1 N2 . 1.315(2) yes
C1 C8 . 1.471(2) yes
N2 N3 . 1.383(2) yes
N3 C2 . 1.318(2) yes
C2 C3 . 1.476(2) yes
C3 N4 . 1.3350(19) ?
C3 C7 . 1.377(2) ?
N4 C4 . 1.334(2) ?
C4 C5 . 1.364(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.372(2) ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 N13 . 1.351(2) ?
C8 C9 . 1.3631(19) ?
C9 C10 . 1.357(2) ?
C9 H9 . 0.93 ?
C10 C11 . 1.362(2) ?
C10 H10 . 0.93 ?
C11 C12 . 1.362(2) ?
C11 H11 . 0.93 ?
C12 N13 . 1.366(2) ?
C12 H12 . 0.93 ?
N5 C14 . 1.275(2) yes
C14 C15 . 1.443(2) yes
C14 H14 . 0.93 ?
C15 C16 . 1.3867(19) ?
C15 C20 . 1.3932(19) ?
C16 C17 . 1.3694(19) ?
C16 H16 . 0.93 ?
C17 C18 . 1.400(2) ?
C17 H17 . 0.93 ?
C18 N6 . 1.364(2) yes
C18 C19 . 1.406(2) ?
C19 C20 . 1.371(2) ?
C19 H19 . 0.93 ?
C20 H20 . 0.93 ?
N6 C22 . 1.433(2) yes
N6 C21 . 1.435(2) yes
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9 N2 0.93 2.57 2.864(2) 99 y
C13 H13 N5 0.93 2.38 2.959(2) 120 y
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
_geom_torsion_publ_flag
C2 N1 C1 N2 -1.20(16) ?
N5 N1 C1 N2 -174.92(12) ?
C2 N1 C1 C8 178.70(14) ?
N5 N1 C1 C8 5.0(2) ?
N1 C1 N2 N3 1.41(15) ?
C8 C1 N2 N3 -178.49(13) ?
C1 N2 N3 C2 -1.08(16) ?
N2 N3 C2 N1 0.33(17) ?
N2 N3 C2 C3 179.03(13) ?
C1 N1 C2 N3 0.50(17) ?
N5 N1 C2 N3 174.25(12) ?
C1 N1 C2 C3 -178.15(14) ?
N5 N1 C2 C3 -4.4(2) ?
N3 C2 C3 N4 -137.81(15) ?
N1 C2 C3 N4 40.7(2) yes
N3 C2 C3 C7 39.6(2) ?
N1 C2 C3 C7 -141.88(16) ?
C7 C3 N4 C4 0.2(2) ?
C2 C3 N4 C4 177.58(15) ?
C3 N4 C4 C5 0.0(3) ?
N4 C4 C5 C6 -0.4(3) ?
C4 C5 C6 C7 0.6(3) ?
C5 C6 C7 C3 -0.3(3) ?
N4 C3 C7 C6 -0.1(3) ?
C2 C3 C7 C6 -177.37(16) ?
N2 C1 C8 N13 -157.77(15) ?
N1 C1 C8 N13 22.3(2) yes
N2 C1 C8 C9 22.9(2) ?
N1 C1 C8 C9 -157.01(13) ?
N13 C8 C9 C10 -1.6(2) ?
C1 C8 C9 C10 177.73(14) ?
C8 C9 C10 C11 0.2(3) ?
C9 C10 C11 C12 1.1(3) ?
C10 C11 C12 N13 -1.2(3) ?
C9 C8 N13 C12 1.5(2) ?
C1 C8 N13 C12 -177.78(15) ?
C11 C12 N13 C8 -0.1(3) ?
C2 N1 N5 C14 66.65(19) ?
C1 N1 N5 C14 -120.89(15) ?
N1 N5 C14 C15 -174.50(10) yes
N5 C14 C15 C16 -163.16(15) ?
N5 C14 C15 C20 17.7(2) yes
C20 C15 C16 C17 -1.9(2) ?
C14 C15 C16 C17 178.92(14) ?
C15 C16 C17 C18 1.8(2) ?
C16 C17 C18 N6 -179.97(16) ?
C16 C17 C18 C19 -0.2(2) ?
N6 C18 C19 C20 178.51(15) ?
C17 C18 C19 C20 -1.3(2) ?
C18 C19 C20 C15 1.2(2) ?
C16 C15 C20 C19 0.4(2) ?
C14 C15 C20 C19 179.56(15) ?
C17 C18 N6 C22 -176.99(17) ?
C19 C18 N6 C22 3.2(3) ?
C17 C18 N6 C21 -1.9(3) ?
C19 C18 N6 C21 178.31(17) ?
