#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/89/2218908.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_2218908
loop_
_publ_author_name
'Akhtar, Tashfeen'
'Hameed, Shahid'
'Zia-ur-Rehman, Muhammad'
'Hussain Bukhari, Tanveer'
'Khan, Islamullah'
_publ_section_title
;
 4-n-Butyl-3-(3-methylphenyl)-1H-1,2,4-triazol-5(4H)-one
;
_journal_coeditor_code           BT2734
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1388
_journal_paper_doi               10.1107/S1600536808019661
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H17 N3 O'
_chemical_formula_moiety         'C13 H17 N3 O'
_chemical_formula_sum            'C13 H17 N3 O'
_chemical_formula_weight         231.30
_chemical_name_systematic
;
4-n-Butyl-3-(3-methylphenyl)-1H-1,2,4-triazol-5(4H)-one
;
_space_group_IT_number           37
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2 -2c'
_symmetry_space_group_name_H-M   'C c c 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.905(5)
_cell_length_b                   18.139(5)
_cell_length_c                   8.145(2)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.2
_cell_measurement_theta_min      2.99
_cell_volume                     2497.6(12)
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8129
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Orthorhombic
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1791
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0462
_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)+(0.0435P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                1118
_reflns_number_total             1791
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2734.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_original_cell_volume        2497.5(11)
_cod_database_code               2218908
_cod_database_fobs_code          2218908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x, -y, z+1/2'
'-x, y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-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 0.09066(14) 0.37056(10) 0.2364(3) 0.0349(5) Uani d . 1
N N2 0.08503(15) 0.41720(12) -0.0051(3) 0.0407(6) Uani d . 1
N N3 0.08408(14) 0.34149(11) -0.0273(3) 0.0412(6) Uani d . 1
O O1 0.09681(11) 0.49894(11) 0.2110(2) 0.0500(6) Uani d . 1
C C1 0.08634(17) 0.23582(14) 0.1565(3) 0.0350(6) Uani d . 1
C C2 0.02844(17) 0.20574(14) 0.2574(4) 0.0449(8) Uani d . 1
H H2 -0.0090 0.2359 0.3072 0.054 Uiso calc R 1
C C3 0.0272(2) 0.13041(15) 0.2829(4) 0.0531(9) Uani d . 1
H H3 -0.0111 0.1100 0.3510 0.064 Uiso calc R 1
C C4 0.08179(19) 0.08554(16) 0.2092(4) 0.0501(8) Uani d . 1
H H4 0.0791 0.0349 0.2257 0.060 Uiso calc R 1
C C5 0.14059(18) 0.11403(14) 0.1111(4) 0.0423(7) Uani d . 1
C C6 0.14204(17) 0.18975(14) 0.0851(3) 0.0389(7) Uani d . 1
H H6 0.1811 0.2099 0.0185 0.047 Uiso calc R 1
C C7 0.08757(16) 0.31523(14) 0.1205(3) 0.0355(6) Uani d . 1
C C8 0.09113(17) 0.43677(14) 0.1525(3) 0.0360(6) Uani d . 1
C C9 0.11284(18) 0.36397(14) 0.4094(3) 0.0385(7) Uani d . 1
H H9A 0.0902 0.3192 0.4546 0.046 Uiso calc R 1
H H9B 0.0916 0.4055 0.4701 0.046 Uiso calc R 1
C C10 0.20182(18) 0.36205(16) 0.4290(4) 0.0475(7) Uani d . 1
H H10A 0.2223 0.3202 0.3683 0.057 Uiso calc R 1
H H10B 0.2239 0.4063 0.3803 0.057 Uiso calc R 1
C C11 0.22993(18) 0.35668(17) 0.6045(4) 0.0499(8) Uani d . 1
H H11A 0.2064 0.3137 0.6557 0.060 Uiso calc R 1
H H11B 0.2125 0.3999 0.6646 0.060 Uiso calc R 1
C C12 0.2024(2) 0.06501(17) 0.0313(5) 0.0615(10) Uani d . 1
H H13A 0.2245 0.0325 0.1123 0.092 Uiso calc R 1
H H13B 0.2436 0.0951 -0.0145 0.092 Uiso calc R 1
H H13C 0.1782 0.0364 -0.0543 0.092 Uiso calc R 1
H H22 0.0837(17) 0.4487(16) -0.097(4) 0.060(10) Uiso d . 1
C C13 0.31893(19) 0.35095(19) 0.6144(5) 0.0622(9) Uani d . 1
H H13D 0.3366 0.3098 0.5500 0.093 Uiso calc R 1
H H13E 0.3345 0.3440 0.7267 0.093 Uiso calc R 1
H H13F 0.3423 0.3955 0.5730 0.093 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C7 N1 C8 107.1(2)
C7 N1 C9 127.6(2)
C8 N1 C9 123.1(2)
C8 N2 N3 113.0(2)
C8 N2 H22 127.2(19)
N3 N2 H22 119.8(19)
C7 N3 N2 104.0(2)
C6 C1 C2 119.3(2)
C6 C1 C7 119.8(3)
C2 C1 C7 120.8(3)
C3 C2 C1 119.2(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C4 C3 C2 120.8(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 121.2(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C5 C6 118.2(3)
C4 C5 C12 121.7(3)
C6 C5 C12 120.1(3)
C5 C6 C1 121.3(3)
C5 C6 H6 119.3
C1 C6 H6 119.3
N3 C7 N1 111.7(2)
N3 C7 C1 123.0(2)
N1 C7 C1 125.2(2)
O1 C8 N2 128.5(3)
O1 C8 N1 127.4(2)
N2 C8 N1 104.1(2)
N1 C9 C10 111.0(2)
N1 C9 H9A 109.4
C10 C9 H9A 109.4
N1 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108.0
C11 C10 C9 114.5(3)
C11 C10 H10A 108.6
C9 C10 H10A 108.6
C11 C10 H10B 108.6
C9 C10 H10B 108.6
H10A C10 H10B 107.6
C10 C11 C13 111.7(3)
C10 C11 H11A 109.3
C13 C11 H11A 109.3
C10 C11 H11B 109.3
C13 C11 H11B 109.3
H11A C11 H11B 108.0
C5 C12 H13A 109.5
C5 C12 H13B 109.5
H13A C12 H13B 109.5
C5 C12 H13C 109.5
H13A C12 H13C 109.5
H13B C12 H13C 109.5
C11 C13 H13D 109.5
C11 C13 H13E 109.5
H13D C13 H13E 109.5
C11 C13 H13F 109.5
H13D C13 H13F 109.5
H13E C13 H13F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.379(3)
N1 C8 1.382(3)
N1 C9 1.463(3)
N2 C8 1.336(4)
N2 N3 1.385(3)
N2 H22 0.94(3)
N3 C7 1.296(3)
O1 C8 1.228(3)
C1 C6 1.387(4)
C1 C2 1.390(4)
C1 C7 1.470(4)
C2 C3 1.382(3)
C2 H2 0.9300
C3 C4 1.369(4)
C3 H3 0.9300
C4 C5 1.376(4)
C4 H4 0.9300
C5 C6 1.390(4)
C5 C12 1.518(4)
C6 H6 0.9300
C9 C10 1.513(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.509(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C13 1.510(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H13A 0.9600
C12 H13B 0.9600
C12 H13C 0.9600
C13 H13D 0.9600
C13 H13E 0.9600
C13 H13F 0.9600
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 H22 O1 3_564 0.94(3) 1.84(3) 2.775(3) 170(3) 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
C8 N2 N3 C7 1.7(3)
C6 C1 C2 C3 -0.6(4)
C7 C1 C2 C3 177.3(3)
C1 C2 C3 C4 -0.5(5)
C2 C3 C4 C5 1.7(5)
C3 C4 C5 C6 -1.6(5)
C3 C4 C5 C12 178.8(3)
C4 C5 C6 C1 0.5(4)
C12 C5 C6 C1 -179.9(3)
C2 C1 C6 C5 0.7(4)
C7 C1 C6 C5 -177.3(3)
N2 N3 C7 N1 0.0(3)
N2 N3 C7 C1 178.7(3)
C8 N1 C7 N3 -1.6(3)
C9 N1 C7 N3 -164.8(3)
C8 N1 C7 C1 179.8(3)
C9 N1 C7 C1 16.6(4)
C6 C1 C7 N3 55.9(4)
C2 C1 C7 N3 -122.1(3)
C6 C1 C7 N1 -125.7(3)
C2 C1 C7 N1 56.4(4)
N3 N2 C8 O1 176.6(3)
N3 N2 C8 N1 -2.6(3)
C7 N1 C8 O1 -176.8(3)
C9 N1 C8 O1 -12.7(5)
C7 N1 C8 N2 2.5(3)
C9 N1 C8 N2 166.6(3)
C7 N1 C9 C10 80.2(3)
C8 N1 C9 C10 -80.5(3)
N1 C9 C10 C11 178.9(2)
C9 C10 C11 C13 177.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740331
