#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228298.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_2228298
loop_
_publ_author_name
'Kashaev, Artyom G.'
'Zimichev, Anatoliy V.'
'Rybakov, Victor B.'
'Klimochkin, Yurij N.'
'Zemtsova, Margarita N.'
_publ_section_title
;
 2,6-Dimethyl-4-(1,3,4-oxadiazol-2-yl)quinoline
;
_journal_coeditor_code           DS2065
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3333
_journal_paper_doi               10.1107/S1600536810048683
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H11 N3 O'
_chemical_formula_moiety         'C13 H11 N3 O'
_chemical_formula_sum            'C13 H11 N3 O'
_chemical_formula_weight         225.25
_chemical_melting_point_gt       448
_chemical_melting_point_lt       449
_chemical_name_systematic
;
2,6-Dimethyl-4-(1,3,4-oxadiazol-2-yl)quinoline
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5372(14)
_cell_length_b                   9.7546(7)
_cell_length_c                   7.3984(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      39.88
_cell_measurement_theta_min      36.28
_cell_volume                     1102.02(15)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2236
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.8649
_exptl_absorpt_correction_T_min  0.3908
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(Walker & Stuart, 1983)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.140
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0669P)²+0.1662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                1855
_reflns_number_total             2236
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2065.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228298
_cod_database_fobs_code          2228298
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.39891(8) 0.63577(13) 0.05252(18) 0.0557(3) Uani d . 1 . .
C C2 0.36926(10) 0.75870(16) 0.0823(2) 0.0549(4) Uani d . 1 . .
C C21 0.42870(12) 0.87852(19) 0.0735(3) 0.0720(5) Uani d . 1 . .
H H21A 0.4875 0.8464 0.0781 0.108 Uiso calc R 1 . .
H H21B 0.4271 0.9383 0.1758 0.108 Uiso calc R 1 . .
H H21C 0.4096 0.9276 -0.0393 0.108 Uiso calc R 1 . .
C C3 0.28466(10) 0.77894(16) 0.1206(2) 0.0537(4) Uani d . 1 . .
H H3 0.2663 0.8673 0.1417 0.064 Uiso calc R 1 . .
C C4 0.22912(9) 0.67122(14) 0.12717(19) 0.0479(3) Uani d . 1 . .
C C5 0.25819(9) 0.53629(15) 0.09414(18) 0.0468(3) Uani d . 1 . .
C C6 0.20838(9) 0.41454(15) 0.09503(19) 0.0505(3) Uani d . 1 . .
H H6 0.1513 0.4206 0.1158 0.061 Uiso calc R 1 . .
C C7 0.24197(10) 0.28864(15) 0.0662(2) 0.0532(4) Uani d . 1 . .
C C71 0.19028(12) 0.15983(16) 0.0748(3) 0.0656(4) Uani d . 1 . .
H H71A 0.1315 0.1829 0.0868 0.098 Uiso calc R 1 . .
H H71B 0.2171 0.1062 0.1789 0.098 Uiso calc R 1 . .
H H71C 0.1891 0.1078 -0.0358 0.098 Uiso calc R 1 . .
C C8 0.32817(11) 0.28112(16) 0.0302(2) 0.0599(4) Uani d . 1 . .
H H8 0.3515 0.1959 0.0097 0.072 Uiso calc R 1 . .
C C9 0.37777(10) 0.39518(17) 0.0249(2) 0.0587(4) Uani d . 1 . .
H H9 0.4340 0.3871 -0.0003 0.070 Uiso calc R 1 . .
C C10 0.34470(9) 0.52589(15) 0.0574(2) 0.0508(3) Uani d . 1 . .
C C11 0.14273(9) 0.69987(15) 0.1721(2) 0.0500(3) Uani d . 1 . .
O O12 0.11965(7) 0.83379(11) 0.18110(16) 0.0631(3) Uani d . 1 . .
C C13 0.03932(11) 0.8249(2) 0.2255(3) 0.0688(5) Uani d . 1 . .
H H13 0.0057 0.9013 0.2419 0.083 Uiso calc R 1 . .
N N14 0.01403(9) 0.70333(17) 0.2429(2) 0.0739(4) Uani d . 1 . .
N N15 0.08253(9) 0.61910(15) 0.2072(2) 0.0651(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
-1 -8 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C10 . . 118.21(12) ?
N1 C2 C3 . . 121.95(14) ?
N1 C2 C21 . . 117.71(14) ?
C3 C2 C21 . . 120.33(14) ?
C2 C21 H21A . . 109.5 ?
C2 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C2 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C4 C3 C2 . . 121.23(14) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 118.75(13) ?
C3 C4 C11 . . 118.15(13) ?
C5 C4 C11 . . 123.09(12) ?
C6 C5 C10 . . 118.46(13) ?
C6 C5 C4 . . 125.54(12) ?
C10 C5 C4 . . 116.00(13) ?
C7 C6 C5 . . 121.84(13) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 118.56(14) ?
C6 C7 C71 . . 121.59(13) ?
C8 C7 C71 . . 119.84(14) ?
C7 C71 H71A . . 109.5 ?
C7 C71 H71B . . 109.5 ?
H71A C71 H71B . . 109.5 ?
C7 C71 H71C . . 109.5 ?
H71A C71 H71C . . 109.5 ?
H71B C71 H71C . . 109.5 ?
C9 C8 C7 . . 121.66(14) ?
C9 C8 H8 . . 119.2 ?
C7 C8 H8 . . 119.2 ?
C8 C9 C10 . . 120.58(13) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
N1 C10 C9 . . 117.26(13) ?
N1 C10 C5 . . 123.86(13) ?
C9 C10 C5 . . 118.88(13) ?
N15 C11 O12 . . 111.76(13) ?
N15 C11 C4 . . 131.21(14) ?
O12 C11 C4 . . 117.03(12) ?
C13 O12 C11 . . 102.38(12) ?
N14 C13 O12 . . 113.79(14) ?
N14 C13 H13 . . 123.1 ?
O12 C13 H13 . . 123.1 ?
C13 N14 N15 . . 105.60(13) ?
C11 N15 N14 . . 106.47(14) ?
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 . 1.3177(19) ?
N1 C10 . 1.3677(18) ?
C2 C3 . 1.408(2) ?
C2 C21 . 1.499(2) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C3 C4 . 1.366(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.4271(19) ?
C4 C11 . 1.4680(19) ?
C5 C6 . 1.4182(19) ?
C5 C10 . 1.4233(19) ?
C6 C7 . 1.366(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.415(2) ?
C7 C71 . 1.499(2) ?
C71 H71A . 0.9600 ?
C71 H71B . 0.9600 ?
C71 H71C . 0.9600 ?
C8 C9 . 1.358(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.412(2) ?
C9 H9 . 0.9300 ?
C11 N15 . 1.286(2) ?
C11 O12 . 1.3596(17) ?
O12 C13 . 1.3508(19) ?
C13 N14 . 1.263(2) ?
C13 H13 . 0.9300 ?
N14 N15 . 1.4075(18) ?
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
C13 H13 N15 2_555 0.93 2.594 3.523(2) 178
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N1 C2 C3 . . . . 0.7(2) ?
C10 N1 C2 C21 . . . . -178.99(14) ?
N1 C2 C3 C4 . . . . -0.4(2) ?
C21 C2 C3 C4 . . . . 179.24(15) ?
C2 C3 C4 C5 . . . . -0.1(2) ?
C2 C3 C4 C11 . . . . 178.58(13) ?
C3 C4 C5 C6 . . . . -179.61(13) ?
C11 C4 C5 C6 . . . . 1.8(2) ?
C3 C4 C5 C10 . . . . 0.3(2) ?
C11 C4 C5 C10 . . . . -178.28(13) ?
C10 C5 C6 C7 . . . . 1.6(2) ?
C4 C5 C6 C7 . . . . -178.43(14) ?
C5 C6 C7 C8 . . . . -1.6(2) ?
C5 C6 C7 C71 . . . . 177.53(14) ?
C6 C7 C8 C9 . . . . 0.4(2) ?
C71 C7 C8 C9 . . . . -178.70(15) ?
C7 C8 C9 C10 . . . . 0.7(3) ?
C2 N1 C10 C9 . . . . 179.94(13) ?
C2 N1 C10 C5 . . . . -0.4(2) ?
C8 C9 C10 N1 . . . . 179.04(14) ?
C8 C9 C10 C5 . . . . -0.6(2) ?
C6 C5 C10 N1 . . . . 179.88(13) ?
C4 C5 C10 N1 . . . . -0.1(2) ?
C6 C5 C10 C9 . . . . -0.5(2) ?
C4 C5 C10 C9 . . . . 179.53(13) ?
C3 C4 C11 N15 . . . . -171.28(16) ?
C5 C4 C11 N15 . . . . 7.4(3) ?
C3 C4 C11 O12 . . . . 8.1(2) ?
C5 C4 C11 O12 . . . . -173.22(12) ?
N15 C11 O12 C13 . . . . 0.07(17) ?
C4 C11 O12 C13 . . . . -179.46(13) ?
C11 O12 C13 N14 . . . . 0.0(2) ?
O12 C13 N14 N15 . . . . -0.1(2) ?
O12 C11 N15 N14 . . . . -0.13(18) ?
C4 C11 N15 N14 . . . . 179.32(15) ?
C13 N14 N15 C11 . . . . 0.14(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231147
