#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102350.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102350
loop_
_publ_author_name
'De-Bao Yang'
'Fang-Ming Liu'
'Song-Wei Shen'
'Ying-Lei Zhou'
'Jia-Wei Ye'
_publ_section_title
;
 Crystal structure of
 1-(2-((1H-1,2,4-triazol-1-yl)methyl)-2,5-diphenyl-1,3,4-oxadiazol-3(2H)-yl)ethanone,
 C19H17N5O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              503
_journal_volume                  223
_journal_year                    2008
_chemical_formula_sum            'C19 H17 N5 O2'
_chemical_formula_weight         347.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.503(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3993(4)
_cell_length_b                   10.8751(7)
_cell_length_c                   21.3560(14)
_cell_measurement_reflns_used    13805
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.08
_cell_volume                     1699.59(18)
_computing_cell_refinement       'Rapid Auto Version 3.0(Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0(Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0(Rigaku 2004)'
_computing_molecular_graphics    'ortep or diamond'
_computing_publication_material  'ortep or diamond'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-axis Spider'
_diffrn_measurement_method       'ω oscillation'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16189
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_correction_T_min  0.9357
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Higashi,T.(1995).Program for Absorption Correction.Rigaku Corporation,Tokyo,Japan.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0146(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0354
_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)+(0.0535P)²+0.4800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                3484
_reflns_number_total             3887
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2411.cff
_cod_data_source_block           mnphso4
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               8102350
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15286(10) 0.80407(7) 0.31831(3) 0.02021(17) Uani 1 1 d . . .
O2 O 0.15405(11) 0.41896(7) 0.31437(4) 0.0295(2) Uani 1 1 d . . .
N1 N 0.23143(12) 0.68919(8) 0.40544(4) 0.02124(19) Uani 1 1 d . . .
N2 N 0.21380(12) 0.61029(8) 0.35259(4) 0.02048(19) Uani 1 1 d . . .
N3 N -0.17265(12) 0.67253(8) 0.30971(4) 0.02089(19) Uani 1 1 d . . .
N4 N -0.20303(13) 0.58898(9) 0.35456(5) 0.0271(2) Uani 1 1 d . . .
N5 N -0.36791(13) 0.76289(10) 0.36232(5) 0.0300(2) Uani 1 1 d . . .
C1 C 0.28310(15) 0.92000(10) 0.47953(5) 0.0247(2) Uani 1 1 d . . .
H1B H 0.3564 0.8537 0.4977 0.030 Uiso 1 1 calc R . .
C2 C 0.26920(16) 1.02681(11) 0.51393(5) 0.0271(2) Uani 1 1 d . . .
H2A H 0.3333 1.0337 0.5557 0.033 Uiso 1 1 calc R . .
C3 C 0.16232(16) 1.12334(10) 0.48754(5) 0.0267(2) Uani 1 1 d . . .
H3A H 0.1532 1.1963 0.5114 0.032 Uiso 1 1 calc R . .
C4 C 0.06836(16) 1.11419(10) 0.42646(6) 0.0269(2) Uani 1 1 d . . .
H4B H -0.0049 1.1807 0.4085 0.032 Uiso 1 1 calc R . .
C5 C 0.08169(15) 1.00773(10) 0.39162(5) 0.0232(2) Uani 1 1 d . . .
H5B H 0.0178 1.0012 0.3498 0.028 Uiso 1 1 calc R . .
C6 C 0.18905(14) 0.91040(9) 0.41822(5) 0.0201(2) Uani 1 1 d . . .
C7 C 0.19585(13) 0.79630(9) 0.38253(5) 0.0192(2) Uani 1 1 d . . .
C8 C 0.15197(14) 0.68010(9) 0.29384(5) 0.0194(2) Uani 1 1 d . . .
C9 C 0.19272(15) 0.48664(10) 0.36023(6) 0.0249(2) Uani 1 1 d . . .
C10 C 0.2253(2) 0.44050(12) 0.42721(6) 0.0378(3) Uani 1 1 d . . .
H10A H 0.2072 0.3512 0.4275 0.057 Uiso 1 1 calc R . .
H10B H 0.1392 0.4802 0.4516 0.057 Uiso 1 1 calc R . .
H10C H 0.3507 0.4600 0.4463 0.057 Uiso 1 1 calc R . .
C11 C 0.27840(13) 0.67412(10) 0.24406(5) 0.0204(2) Uani 1 1 d . . .
C12 C 0.40128(14) 0.57802(10) 0.24154(5) 0.0234(2) Uani 1 1 d . . .
H12A H 0.4110 0.5147 0.2725 0.028 Uiso 1 1 calc R . .
C13 C 0.50992(15) 0.57456(11) 0.19362(6) 0.0276(2) Uani 1 1 d . . .
H13A H 0.5914 0.5077 0.1913 0.033 Uiso 1 1 calc R . .
C14 C 0.49971(16) 0.66816(12) 0.14928(6) 0.0305(3) Uani 1 1 d . . .
H14A H 0.5744 0.6658 0.1168 0.037 Uiso 1 1 calc R . .
C15 C 0.37996(17) 0.76544(12) 0.15252(6) 0.0313(3) Uani 1 1 d . . .
H15A H 0.3747 0.8305 0.1226 0.038 Uiso 1 1 calc R . .
C16 C 0.26761(15) 0.76818(11) 0.19926(5) 0.0264(2) Uani 1 1 d . . .
H16A H 0.1838 0.8339 0.2007 0.032 Uiso 1 1 calc R . .
C17 C -0.04649(14) 0.64959(10) 0.26524(5) 0.0214(2) Uani 1 1 d . . .
H17A H -0.0820 0.7001 0.2268 0.026 Uiso 1 1 calc R . .
H17B H -0.0543 0.5620 0.2525 0.026 Uiso 1 1 calc R . .
C18 C -0.32091(16) 0.64872(12) 0.38417(5) 0.0293(3) Uani 1 1 d . . .
H18A H -0.3698 0.6136 0.4188 0.035 Uiso 1 1 calc R . .
C19 C -0.27136(15) 0.77413(10) 0.31540(5) 0.0252(2) Uani 1 1 d . . .
H19A H -0.2718 0.8447 0.2892 0.030 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 107.07(7) . . ?
C7 N1 N2 105.04(8) . . ?
C9 N2 N1 120.17(9) . . ?
C9 N2 C8 125.43(9) . . ?
N1 N2 C8 110.32(8) . . ?
C19 N3 N4 109.71(9) . . ?
C19 N3 C17 127.90(9) . . ?
N4 N3 C17 122.36(9) . . ?
C18 N4 N3 101.40(9) . . ?
C19 N5 C18 101.92(10) . . ?
C2 C1 C6 119.67(10) . . ?
C2 C1 H1B 120.2 . . ?
C6 C1 H1B 120.2 . . ?
C3 C2 C1 120.19(10) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 120.34(10) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.89(11) . . ?
C5 C4 H4B 120.1 . . ?
C3 C4 H4B 120.1 . . ?
C4 C5 C6 119.79(10) . . ?
C4 C5 H5B 120.1 . . ?
C6 C5 H5B 120.1 . . ?
C5 C6 C1 120.12(10) . . ?
C5 C6 C7 119.61(9) . . ?
C1 C6 C7 120.21(10) . . ?
N1 C7 O1 116.52(9) . . ?
N1 C7 C6 126.62(9) . . ?
O1 C7 C6 116.81(9) . . ?
O1 C8 N2 100.82(7) . . ?
O1 C8 C11 108.84(8) . . ?
N2 C8 C11 115.25(8) . . ?
O1 C8 C17 107.29(8) . . ?
N2 C8 C17 112.49(8) . . ?
C11 C8 C17 111.29(8) . . ?
O2 C9 N2 120.88(11) . . ?
O2 C9 C10 123.14(11) . . ?
N2 C9 C10 115.96(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 119.72(10) . . ?
C12 C11 C8 122.22(10) . . ?
C16 C11 C8 118.05(9) . . ?
C11 C12 C13 120.02(11) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 120.25(10) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 119.79(10) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.38(11) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 119.80(11) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?
N3 C17 C8 111.83(8) . . ?
N3 C17 H17A 109.2 . . ?
C8 C17 H17A 109.2 . . ?
N3 C17 H17B 109.2 . . ?
C8 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N4 C18 N5 116.11(10) . . ?
N4 C18 H18A 121.9 . . ?
N5 C18 H18A 121.9 . . ?
N5 C19 N3 110.86(10) . . ?
N5 C19 H19A 124.6 . . ?
N3 C19 H19A 124.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.3639(12) . ?
O1 C8 1.4456(12) . ?
O2 C9 1.2248(14) . ?
N1 C7 1.2757(14) . ?
N1 N2 1.4084(12) . ?
N2 C9 1.3663(14) . ?
N2 C8 1.4799(13) . ?
N3 C19 1.3398(14) . ?
N3 N4 1.3628(13) . ?
N3 C17 1.4484(13) . ?
N4 C18 1.3214(15) . ?
N5 C19 1.3194(15) . ?
N5 C18 1.3536(17) . ?
C1 C2 1.3862(15) . ?
C1 C6 1.3930(15) . ?
C1 H1B 0.9500 . ?
C2 C3 1.3832(17) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3881(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3877(15) . ?
C4 H4B 0.9500 . ?
C5 C6 1.3931(15) . ?
C5 H5B 0.9500 . ?
C6 C7 1.4610(14) . ?
C8 C11 1.5178(14) . ?
C8 C17 1.5409(14) . ?
C9 C10 1.5014(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3915(15) . ?
C11 C16 1.3949(15) . ?
C12 C13 1.3921(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3846(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3882(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3906(16) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 -161.84(9) . . . . ?
C7 N1 N2 C8 -3.35(11) . . . . ?
C19 N3 N4 C18 0.14(12) . . . . ?
C17 N3 N4 C18 178.61(9) . . . . ?
C6 C1 C2 C3 0.08(16) . . . . ?
C1 C2 C3 C4 -0.08(17) . . . . ?
C2 C3 C4 C5 -0.04(17) . . . . ?
C3 C4 C5 C6 0.16(16) . . . . ?
C4 C5 C6 C1 -0.16(15) . . . . ?
C4 C5 C6 C7 177.11(9) . . . . ?
C2 C1 C6 C5 0.04(16) . . . . ?
C2 C1 C6 C7 -177.21(10) . . . . ?
N2 N1 C7 O1 0.37(12) . . . . ?
N2 N1 C7 C6 177.61(9) . . . . ?
C8 O1 C7 N1 2.77(12) . . . . ?
C8 O1 C7 C6 -174.75(8) . . . . ?
C5 C6 C7 N1 -154.21(10) . . . . ?
C1 C6 C7 N1 23.05(16) . . . . ?
C5 C6 C7 O1 23.02(13) . . . . ?
C1 C6 C7 O1 -159.72(9) . . . . ?
C7 O1 C8 N2 -4.30(9) . . . . ?
C7 O1 C8 C11 -125.91(8) . . . . ?
C7 O1 C8 C17 113.56(9) . . . . ?
C9 N2 C8 O1 161.83(9) . . . . ?
N1 N2 C8 O1 4.73(10) . . . . ?
C9 N2 C8 C11 -81.20(12) . . . . ?
N1 N2 C8 C11 121.70(9) . . . . ?
C9 N2 C8 C17 47.84(13) . . . . ?
N1 N2 C8 C17 -109.26(9) . . . . ?
N1 N2 C9 O2 170.61(9) . . . . ?
C8 N2 C9 O2 15.58(16) . . . . ?
N1 N2 C9 C10 -11.14(15) . . . . ?
C8 N2 C9 C10 -166.18(10) . . . . ?
O1 C8 C11 C12 135.82(10) . . . . ?
N2 C8 C11 C12 23.48(13) . . . . ?
C17 C8 C11 C12 -106.14(11) . . . . ?
O1 C8 C11 C16 -44.95(12) . . . . ?
N2 C8 C11 C16 -157.29(9) . . . . ?
C17 C8 C11 C16 73.09(12) . . . . ?
C16 C11 C12 C13 -1.43(15) . . . . ?
C8 C11 C12 C13 177.78(9) . . . . ?
C11 C12 C13 C14 1.68(16) . . . . ?
C12 C13 C14 C15 -0.32(17) . . . . ?
C13 C14 C15 C16 -1.28(18) . . . . ?
C14 C15 C16 C11 1.52(18) . . . . ?
C12 C11 C16 C15 -0.16(16) . . . . ?
C8 C11 C16 C15 -179.41(10) . . . . ?
C19 N3 C17 C8 94.57(12) . . . . ?
N4 N3 C17 C8 -83.60(12) . . . . ?
O1 C8 C17 N3 -52.52(11) . . . . ?
N2 C8 C17 N3 57.46(11) . . . . ?
C11 C8 C17 N3 -171.48(8) . . . . ?
N3 N4 C18 N5 -0.17(13) . . . . ?
C19 N5 C18 N4 0.12(13) . . . . ?
C18 N5 C19 N3 -0.02(12) . . . . ?
N4 N3 C19 N5 -0.08(13) . . . . ?
C17 N3 C19 N5 -178.44(9) . . . . ?
