#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210504.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_2210504
loop_
_publ_author_name
'Song, Qing-Bao'
'Zhang, Jie'
'Yu Dong'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-[5-(3,6-Dichloropyridin-2-yl)-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone
;
_journal_coeditor_code           BI2059
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4388
_journal_page_last               o4390
_journal_paper_doi               10.1107/S1600536806035926
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H11 Cl2 N3 O2'
_chemical_formula_moiety         'C11 H11 Cl2 N3 O2'
_chemical_formula_sum            'C11 H11 Cl2 N3 O2'
_chemical_formula_weight         288.13
_chemical_name_systematic
;
1-[5-(3,6-Dichloropyridin-2-yl)-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.554(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1149(19)
_cell_length_b                   8.1943(13)
_cell_length_c                   14.122(2)
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.9
_cell_volume                     1283.7(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku AFC12κ/SATURN724 CCD'
_diffrn_measurement_method       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  0.029
_diffrn_reflns_av_sigmaI/netI    0.012
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32711
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.18
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.18
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.040
_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)+(0.0762P)²+0.4744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.123
_refine_ls_wR_factor_ref         0.135
_reflns_number_gt                2887
_reflns_number_total             2924
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2059.cif
_cod_data_source_block           I
_cod_original_cell_volume        1283.8(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210504
_cod_database_fobs_code          2210504
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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
Cl Cl1 0.93462(4) 0.87254(8) -0.10314(4) 0.0523(2) Uani d . 1
Cl Cl2 0.77170(4) 0.48665(7) 0.24046(3) 0.04466(18) Uani d . 1
O O1 0.54047(10) 0.80222(15) 0.04455(9) 0.0317(3) Uani d . 1
O O2 0.22748(11) 0.57282(17) 0.13400(10) 0.0380(3) Uani d . 1
N N1 0.54303(12) 0.56763(18) 0.12651(10) 0.0278(3) Uani d . 1
N N2 0.42304(12) 0.61429(17) 0.10955(10) 0.0275(3) Uani d . 1
N N3 0.77364(13) 0.76615(18) 0.00831(11) 0.0298(3) Uani d . 1
C C1 0.60406(14) 0.67882(19) 0.08809(11) 0.0258(3) Uani d . 1
C C2 0.41458(14) 0.7796(2) 0.06637(11) 0.0264(3) Uani d . 1
C C3 0.33179(15) 0.5243(2) 0.14320(12) 0.0280(3) Uani d . 1
C C4 0.36809(16) 0.3651(2) 0.18937(12) 0.0319(4) Uani d . 1
H H4A 0.2958 0.3045 0.2046 0.048 Uiso calc R 1
H H4B 0.4179 0.3863 0.2477 0.048 Uiso calc R 1
H H4C 0.4142 0.3005 0.1458 0.048 Uiso calc R 1
C C5 0.38273(19) 0.9073(2) 0.13736(14) 0.0388(4) Uani d . 1
H H5A 0.2985 0.8935 0.1526 0.058 Uiso calc R 1
H H5B 0.3936 1.0161 0.1104 0.058 Uiso calc R 1
H H5C 0.4353 0.8954 0.1953 0.058 Uiso calc R 1
C C6 0.33842(15) 0.7869(2) -0.02577(12) 0.0331(4) Uani d . 1
H H6A 0.2534 0.7722 -0.0131 0.050 Uiso calc R 1
H H6B 0.3633 0.7001 -0.0681 0.050 Uiso calc R 1
H H6C 0.3491 0.8932 -0.0560 0.050 Uiso calc R 1
C C7 0.73568(14) 0.6799(2) 0.08202(11) 0.0261(3) Uani d . 1
C C8 0.88991(15) 0.7670(2) -0.00442(13) 0.0332(4) Uani d . 1
C C9 0.97700(16) 0.6893(3) 0.05348(14) 0.0380(4) Uani d . 1
H H9 1.0600 0.6955 0.0412 0.046 Uiso calc R 1
C C10 0.93898(16) 0.6032(2) 0.12927(14) 0.0368(4) Uani d . 1
H H10 0.9957 0.5488 0.1713 0.044 Uiso calc R 1
C C11 0.81627(15) 0.5962(2) 0.14419(12) 0.0300(3) 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C1 O1 C2 106.74(12) y
N2 N1 C1 105.01(13) y
N1 N2 C2 110.86(12) y
N1 N2 C3 121.08(14) y
C2 N2 C3 127.35(13) y
C8 N3 C7 117.74(15) y
N1 C1 O1 116.63(14) ?
N1 C1 C7 125.84(15) ?
O1 C1 C7 117.42(14) ?
O1 C2 N2 99.48(11) ?
O1 C2 C5 108.65(14) ?
N2 C2 C5 111.81(14) ?
O1 C2 C6 107.83(13) ?
N2 C2 C6 114.05(14) ?
C5 C2 C6 113.84(14) ?
O2 C3 N2 120.47(16) ?
O2 C3 C4 123.71(16) ?
N2 C3 C4 115.82(14) ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C2 C5 H5A 109.5 ?
C2 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C2 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C2 C6 H6A 109.5 ?
C2 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C2 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
N3 C7 C11 121.64(15) ?
N3 C7 C1 114.10(14) ?
C11 C7 C1 124.23(15) ?
N3 C8 C9 125.05(17) ?
N3 C8 Cl1 116.35(13) ?
C9 C8 Cl1 118.59(14) ?
C8 C9 C10 117.40(16) ?
C8 C9 H9 121.3 ?
C10 C9 H9 121.3 ?
C11 C10 C9 119.43(16) ?
C11 C10 H10 120.3 ?
C9 C10 H10 120.3 ?
C7 C11 C10 118.71(16) ?
C7 C11 Cl2 123.14(13) ?
C10 C11 Cl2 118.14(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C8 1.7392(18) ?
Cl2 C11 1.7270(18) ?
O1 C1 1.3587(19) y
O1 C2 1.4630(18) y
O2 C3 1.225(2) y
N1 C1 1.277(2) y
N1 N2 1.3938(18) y
N2 C2 1.486(2) y
N2 C3 1.363(2) y
N3 C7 1.347(2) y
N3 C8 1.316(2) y
C1 C7 1.471(2) ?
C2 C5 1.506(2) ?
C2 C6 1.509(2) ?
C3 C4 1.503(2) ?
C4 H4A 0.980 ?
C4 H4B 0.980 ?
C4 H4C 0.980 ?
C5 H5A 0.980 ?
C5 H5B 0.980 ?
C5 H5C 0.980 ?
C6 H6A 0.980 ?
C6 H6B 0.980 ?
C6 H6C 0.980 ?
C7 C11 1.395(2) ?
C8 C9 1.383(3) ?
C9 C10 1.370(3) ?
C9 H9 0.950 ?
C10 C11 1.394(2) ?
C10 H10 0.950 ?
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
C9 H9 O2 1_655 0.95 2.43 3.092(2) 127 y
C6 H6B N1 3_665 0.98 2.59 3.526(2) 161 y
C4 H4B Cl1 4_576 0.98 2.89 3.672(2) 138 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13086834
