#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203684.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_2203684
loop_
_publ_author_name
'Shao, Si-Chang'
'Liu, Hui-Jun'
'Zhang, Shu-Ping'
'Yang, Song'
'Hao, Fu-Ying'
'Li, Cheng-Peng'
'Zhu, Hai-Liang'
_publ_section_title
;
4-(3,4-Dimethylphenyl)-3,5-di-2-pyridyl-4H-1,2,4-triazole
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o722
_journal_page_last               o723
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H17 N5'
_chemical_formula_moiety         'C20 H17 N5'
_chemical_formula_sum            'C20 H17 N5'
_chemical_formula_weight         327.39
_chemical_name_systematic
;
4-(3,4-Dimethylphenyl)-3,5-di-2-pyridyl-4H-1,2,4-triazole
;
_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
_cell_angle_alpha                82.630(5)
_cell_angle_beta                 62.925(5)
_cell_angle_gamma                63.291(5)
_cell_formula_units_Z            2
_cell_length_a                   10.006(3)
_cell_length_b                   10.318(3)
_cell_length_c                   10.371(3)
_cell_measurement_reflns_used    979
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.49
_cell_measurement_theta_min      2.518
_cell_volume                     847.7(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4485
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0456P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                1530
_reflns_number_total             2954
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ww6178.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               2203684
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
N1 0.2576(2) 0.4342(2) 0.0180(2) 0.0443(6) Uani d . 1 N
N2 0.3253(3) 0.2051(2) -0.0289(2) 0.0616(7) Uani d . 1 N
N3 0.3246(3) 0.2766(2) -0.1507(2) 0.0593(7) Uani d . 1 N
N4 0.1628(3) 0.3565(2) 0.3287(2) 0.0550(6) Uani d . 1 N
N5 0.3793(3) 0.5879(2) -0.2439(2) 0.0567(6) Uani d . 1 N
C1 0.2860(3) 0.3006(3) 0.0705(3) 0.0470(7) Uani d . 1 C
C2 0.2842(3) 0.4129(3) -0.1205(3) 0.0461(7) Uani d . 1 C
C3 0.2804(3) 0.2602(3) 0.2134(3) 0.0460(7) Uani d . 1 C
C4 0.3947(3) 0.1236(3) 0.2220(3) 0.0557(7) Uani d . 1 C
H4A 0.4752 0.0594 0.1389 0.067 Uiso calc R 1 H
C5 0.3861(4) 0.0850(3) 0.3565(3) 0.0660(8) Uani d . 1 C
H5A 0.4604 -0.0064 0.3661 0.079 Uiso calc R 1 H
C6 0.2673(4) 0.1826(3) 0.4757(3) 0.0682(9) Uani d . 1 C
H6A 0.2601 0.1597 0.5676 0.082 Uiso calc R 1 H
C7 0.1589(4) 0.3149(3) 0.4572(3) 0.0640(8) Uani d . 1 C
H7A 0.0772 0.3801 0.5393 0.077 Uiso calc R 1 H
C8 0.2884(3) 0.5195(3) -0.2288(3) 0.0471(7) Uani d . 1 C
C9 0.2127(3) 0.5372(3) -0.3162(3) 0.0626(8) Uani d . 1 C
H9A 0.1477 0.4894 -0.3009 0.075 Uiso calc R 1 H
C10 0.2341(4) 0.6266(3) -0.4266(3) 0.0728(9) Uani d . 1 C
H10A 0.1840 0.6403 -0.4871 0.087 Uiso calc R 1 H
C11 0.3303(4) 0.6947(3) -0.4455(3) 0.0672(9) Uani d . 1 C
H11A 0.3497 0.7540 -0.5205 0.081 Uiso calc R 1 H
C12 0.3971(3) 0.6732(3) -0.3512(3) 0.0655(8) Uani d . 1 C
H12A 0.4600 0.7222 -0.3631 0.079 Uiso calc R 1 H
C13 0.2100(3) 0.5706(3) 0.0880(2) 0.0428(6) Uani d . 1 C
C14 0.0683(3) 0.6906(3) 0.0961(2) 0.0467(7) Uani d . 1 C
H14A 0.0014 0.6814 0.0618 0.056 Uiso calc R 1 H
C15 0.0236(3) 0.8273(3) 0.1559(3) 0.0499(7) Uani d . 1 C
C16 0.1265(4) 0.8370(3) 0.2062(3) 0.0591(8) Uani d . 1 C
C17 0.2641(4) 0.7147(3) 0.1994(3) 0.0603(8) Uani d . 1 C
H17A 0.3300 0.7224 0.2359 0.072 Uiso calc R 1 H
C18 0.3090(3) 0.5809(3) 0.1408(3) 0.0506(7) Uani d . 1 C
H18A 0.4038 0.4993 0.1369 0.061 Uiso calc R 1 H
C19 -0.1306(3) 0.9553(3) 0.1632(3) 0.0725(9) Uani d . 1 C
H19A -0.1440 1.0402 0.2061 0.109 Uiso calc R 1 H
H19B -0.2261 0.9369 0.2215 0.109 Uiso calc R 1 H
H19C -0.1212 0.9714 0.0669 0.109 Uiso calc R 1 H
C20 0.0835(5) 0.9831(3) 0.2699(4) 0.1001(12) Uani d . 1 C
H20A 0.1662 0.9716 0.2991 0.150 Uiso calc R 1 H
H20B -0.0245 1.0186 0.3528 0.150 Uiso calc R 1 H
H20C 0.0817 1.0515 0.1979 0.150 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0456(13) 0.0378(13) 0.0451(13) -0.0116(10) -0.0219(11) -0.0030(10)
N2 0.0760(17) 0.0474(14) 0.0604(15) -0.0204(13) -0.0349(13) -0.0014(12)
N3 0.0682(17) 0.0500(15) 0.0573(15) -0.0178(13) -0.0324(13) -0.0033(12)
N4 0.0496(14) 0.0508(14) 0.0516(14) -0.0111(12) -0.0220(12) -0.0015(12)
N5 0.0513(15) 0.0607(15) 0.0608(15) -0.0248(13) -0.0272(12) 0.0053(13)
C1 0.0432(16) 0.0395(16) 0.0510(16) -0.0116(13) -0.0200(13) -0.0038(13)
C2 0.0427(16) 0.0463(17) 0.0488(16) -0.0145(13) -0.0232(13) -0.0034(14)
C3 0.0469(16) 0.0393(16) 0.0511(16) -0.0173(14) -0.0230(14) 0.0033(13)
C4 0.0513(18) 0.0439(17) 0.0620(18) -0.0131(14) -0.0240(15) -0.0011(14)
C5 0.061(2) 0.0528(19) 0.082(2) -0.0222(16) -0.0384(18) 0.0233(17)
C6 0.064(2) 0.075(2) 0.0598(19) -0.0297(18) -0.0287(17) 0.0255(17)
C7 0.057(2) 0.069(2) 0.0511(18) -0.0202(17) -0.0196(15) 0.0015(16)
C8 0.0433(16) 0.0490(17) 0.0445(16) -0.0145(14) -0.0195(13) -0.0059(13)
C9 0.065(2) 0.077(2) 0.0562(18) -0.0346(17) -0.0315(16) 0.0054(16)
C10 0.077(2) 0.087(2) 0.059(2) -0.032(2) -0.0406(18) 0.0112(18)
C11 0.071(2) 0.060(2) 0.0559(19) -0.0215(18) -0.0250(17) 0.0080(15)
C12 0.064(2) 0.064(2) 0.068(2) -0.0325(17) -0.0242(17) 0.0038(17)
C13 0.0430(16) 0.0373(15) 0.0401(14) -0.0136(13) -0.0153(12) -0.0014(12)
C14 0.0419(16) 0.0477(17) 0.0449(15) -0.0182(14) -0.0164(13) 0.0033(13)
C15 0.0435(16) 0.0372(16) 0.0452(15) -0.0114(13) -0.0077(13) 0.0030(12)
C16 0.065(2) 0.057(2) 0.0552(17) -0.0326(17) -0.0193(16) -0.0013(14)
C17 0.0576(19) 0.074(2) 0.0531(18) -0.0331(17) -0.0220(15) -0.0019(16)
C18 0.0474(17) 0.0568(19) 0.0451(15) -0.0215(14) -0.0183(13) -0.0025(13)
C19 0.062(2) 0.0526(19) 0.075(2) -0.0162(16) -0.0181(16) 0.0076(15)
C20 0.124(3) 0.072(2) 0.109(3) -0.048(2) -0.044(2) -0.020(2)
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
C2 N1 C1 104.8(2)
C2 N1 C13 125.5(2)
C1 N1 C13 129.7(2)
C1 N2 N3 107.4(2)
C2 N3 N2 107.34(19)
C3 N4 C7 116.4(2)
C12 N5 C8 116.4(2)
N2 C1 N1 110.0(2)
N2 C1 C3 122.1(2)
N1 C1 C3 127.8(2)
N3 C2 N1 110.3(2)
N3 C2 C8 123.3(2)
N1 C2 C8 126.0(2)
N4 C3 C4 123.3(2)
N4 C3 C1 118.0(2)
C4 C3 C1 118.6(2)
C5 C4 C3 118.3(2)
C5 C4 H4A 120.8
C3 C4 H4A 120.8
C6 C5 C4 119.1(3)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
C5 C6 C7 118.6(3)
C5 C6 H6A 120.7
C7 C6 H6A 120.7
N4 C7 C6 124.2(3)
N4 C7 H7A 117.9
C6 C7 H7A 117.9
N5 C8 C9 122.9(3)
N5 C8 C2 116.1(2)
C9 C8 C2 120.8(3)
C10 C9 C8 119.1(3)
C10 C9 H9A 120.4
C8 C9 H9A 120.4
C9 C10 C11 118.6(3)
C9 C10 H10A 120.7
C11 C10 H10A 120.7
C12 C11 C10 118.0(3)
C12 C11 H11A 121.0
C10 C11 H11A 121.0
N5 C12 C11 124.9(3)
N5 C12 H12A 117.5
C11 C12 H12A 117.5
C14 C13 C18 120.9(2)
C14 C13 N1 119.0(2)
C18 C13 N1 120.1(2)
C13 C14 C15 120.4(2)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C16 C15 C14 118.2(2)
C16 C15 C19 122.6(3)
C14 C15 C19 119.2(3)
C17 C16 C15 119.7(3)
C17 C16 C20 120.6(3)
C15 C16 C20 119.7(3)
C16 C17 C18 122.5(3)
C16 C17 H17A 118.7
C18 C17 H17A 118.7
C17 C18 C13 118.2(2)
C17 C18 H18A 120.9
C13 C18 H18A 120.9
C15 C19 H19A 109.5
C15 C19 H19B 109.5
H19A C19 H19B 109.5
C15 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C16 C20 H20A 109.5
C16 C20 H20B 109.5
H20A C20 H20B 109.5
C16 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.365(3) yes
N1 C1 1.369(3) yes
N1 C13 1.442(3) yes
N2 C1 1.317(3) yes
N2 N3 1.380(3) yes
N3 C2 1.314(3) yes
N4 C3 1.332(3) yes
N4 C7 1.335(3) yes
N5 C12 1.325(3) yes
N5 C8 1.330(3) yes
C1 C3 1.469(3) ?
C2 C8 1.467(3) ?
C3 C4 1.384(3) ?
C4 C5 1.376(3) ?
C4 H4A 0.9300 ?
C5 C6 1.364(4) ?
C5 H5A 0.9300 ?
C6 C7 1.367(3) ?
C6 H6A 0.9300 ?
C7 H7A 0.9300 ?
C8 C9 1.373(3) ?
C9 C10 1.375(4) ?
C9 H9A 0.9300 ?
C10 C11 1.363(4) ?
C10 H10A 0.9300 ?
C11 C12 1.364(4) ?
C11 H11A 0.9300 ?
C12 H12A 0.9300 ?
C13 C14 1.375(3) ?
C13 C18 1.377(3) ?
C14 C15 1.407(3) ?
C14 H14A 0.9300 ?
C15 C16 1.391(4) ?
C15 C19 1.490(3) yes
C16 C17 1.366(4) ?
C16 C20 1.519(3) ?
C17 C18 1.374(3) ?
C17 H17A 0.9300 ?
C18 H18A 0.9300 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
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
C1 N2 N3 C2 -0.3(3) ?
N3 N2 C1 N1 0.6(3) ?
N3 N2 C1 C3 -178.0(2) ?
C2 N1 C1 N2 -0.7(3) ?
C13 N1 C1 N2 179.3(2) ?
C2 N1 C1 C3 177.8(2) ?
C13 N1 C1 C3 -2.3(4) ?
N2 N3 C2 N1 -0.2(3) ?
N2 N3 C2 C8 173.1(2) ?
C1 N1 C2 N3 0.5(3) ?
C13 N1 C2 N3 -179.4(2) ?
C1 N1 C2 C8 -172.5(2) ?
C13 N1 C2 C8 7.5(4) ?
C7 N4 C3 C4 -0.1(4) ?
C7 N4 C3 C1 178.5(2) ?
N2 C1 C3 N4 -143.6(3) yes
N1 C1 C3 N4 38.1(4) ?
N2 C1 C3 C4 35.0(4) ?
N1 C1 C3 C4 -143.3(3) ?
N4 C3 C4 C5 0.2(4) ?
C1 C3 C4 C5 -178.4(3) ?
C3 C4 C5 C6 -0.6(4) ?
C4 C5 C6 C7 1.0(4) ?
C3 N4 C7 C6 0.5(4) ?
C5 C6 C7 N4 -1.0(5) ?
C12 N5 C8 C9 -1.5(4) ?
C12 N5 C8 C2 173.5(2) ?
N3 C2 C8 N5 -125.4(3) ?
N1 C2 C8 N5 46.8(3) ?
N3 C2 C8 C9 49.7(3) yes
N1 C2 C8 C9 -138.1(3) ?
N5 C8 C9 C10 1.6(4) ?
C2 C8 C9 C10 -173.2(2) ?
C8 C9 C10 C11 0.0(4) ?
C9 C10 C11 C12 -1.6(4) ?
C8 N5 C12 C11 -0.2(4) ?
C10 C11 C12 N5 1.8(4) ?
C2 N1 C13 C14 55.7(3) ?
C1 N1 C13 C14 -124.3(3) ?
C2 N1 C13 C18 -121.9(3) ?
C1 N1 C13 C18 58.1(3) yes
C18 C13 C14 C15 1.4(4) ?
N1 C13 C14 C15 -176.2(2) ?
C13 C14 C15 C16 0.0(3) ?
C13 C14 C15 C19 180.0(2) ?
C14 C15 C16 C17 -1.5(4) ?
C19 C15 C16 C17 178.5(2) ?
C14 C15 C16 C20 179.3(2) ?
C19 C15 C16 C20 -0.7(4) yes
C15 C16 C17 C18 1.8(4) ?
C20 C16 C17 C18 -179.0(2) ?
C16 C17 C18 C13 -0.4(4) ?
C14 C13 C18 C17 -1.2(4) ?
N1 C13 C18 C17 176.4(2) ?