#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210217.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_2210217
loop_
_publ_author_name
'Song, Qing-Bao'
'Zhang, Jie'
'Tiekink, Edward R. T.'
_publ_section_title
;2-[3-Acetyl-5-(3,6-dichloropyridin-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl]phenyl
 acetate
;
_journal_coeditor_code           EZ2027
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4115
_journal_page_last               o4117
_journal_paper_doi               10.1107/S1600536806033605
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H13 Cl2 N3 O4'
_chemical_formula_moiety         'C17 H13 Cl2 N3 O4'
_chemical_formula_sum            'C17 H13 Cl2 N3 O4'
_chemical_formula_weight         394.20
_chemical_name_systematic
;
2-[3-Acetyl-5-(3,6-dichloropyridin-2-yl)-2,3-dihydro-1,3,4-oxadiazol-
2-yl]phenyl acetate
;
_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
_cell_angle_beta                 105.658(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.839(4)
_cell_length_b                   7.917(3)
_cell_length_c                   19.255(7)
_cell_measurement_reflns_used    7799
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.2
_cell_volume                     1737.8(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.013
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45244
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.16
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0598P)²+0.6091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.115
_refine_ls_wR_factor_ref         0.116
_reflns_number_gt                3911
_reflns_number_total             3956
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2027.cif
_cod_data_source_block           I
_cod_original_cell_volume        1737.6(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210217
_cod_database_fobs_code          2210217
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
Cl Cl1 0.48052(4) 0.23291(5) 0.58331(2) 0.03789(13) Uani d . 1
Cl Cl2 0.04411(4) -0.21332(6) 0.55474(3) 0.04736(14) Uani d . 1
O O1 0.25459(9) -0.02089(14) 0.38154(5) 0.0298(2) Uani d . 1
O O2 0.45798(11) 0.17231(16) 0.25855(6) 0.0408(3) Uani d . 1
O O3 0.16906(10) 0.32542(14) 0.34882(6) 0.0316(2) Uani d . 1
O O4 0.25871(14) 0.54765(19) 0.31337(7) 0.0557(4) Uani d . 1
N N1 0.19930(12) -0.05955(16) 0.50423(7) 0.0297(3) Uani d . 1
N N2 0.40095(11) 0.16292(16) 0.42805(6) 0.0294(3) Uani d . 1
N N3 0.39041(11) 0.14552(17) 0.35489(7) 0.0305(3) Uani d . 1
C C1 0.32140(13) 0.06568(18) 0.43967(7) 0.0272(3) Uani d . 1
C C2 0.29341(13) 0.03139(19) 0.32006(7) 0.0288(3) Uani d . 1
H H2 0.3240 -0.0678 0.2986 0.035 Uiso calc R 1
C C3 0.29372(13) 0.03905(18) 0.50851(7) 0.0271(3) Uani d . 1
C C4 0.35774(14) 0.10874(19) 0.57434(8) 0.0301(3) Uani d . 1
C C5 0.32249(15) 0.0743(2) 0.63595(8) 0.0362(4) Uani d . 1
H H5 0.3648 0.1198 0.6811 0.043 Uiso calc R 1
C C6 0.22593(16) -0.0262(2) 0.63137(8) 0.0374(4) Uani d . 1
H H6 0.1999 -0.0520 0.6727 0.045 Uiso calc R 1
C C7 0.16817(14) -0.0880(2) 0.56353(8) 0.0325(3) Uani d . 1
C C8 0.46718(14) 0.2126(2) 0.32090(9) 0.0315(3) Uani d . 1
C C9 0.55533(16) 0.3366(2) 0.36294(10) 0.0402(4) Uani d . 1
H H9A 0.6284 0.3266 0.3486 0.060 Uiso calc R 1
H H9B 0.5708 0.3127 0.4146 0.060 Uiso calc R 1
H H9C 0.5243 0.4515 0.3531 0.060 Uiso calc R 1
C C10 0.19631(13) 0.11692(19) 0.26380(7) 0.0281(3) Uani d . 1
C C11 0.13857(14) 0.26011(19) 0.27843(8) 0.0287(3) Uani d . 1
C C12 0.04761(14) 0.3348(2) 0.22653(9) 0.0344(3) Uani d . 1
H H12 0.0083 0.4310 0.2381 0.041 Uiso calc R 1
C C13 0.01478(15) 0.2673(2) 0.15757(9) 0.0366(4) Uani d . 1
H H13 -0.0467 0.3181 0.1214 0.044 Uiso calc R 1
C C14 0.07173(15) 0.1258(2) 0.14134(8) 0.0363(3) Uani d . 1
H H14 0.0494 0.0801 0.0940 0.044 Uiso calc R 1
C C15 0.16141(14) 0.0503(2) 0.19416(8) 0.0324(3) Uani d . 1
H H15 0.1993 -0.0476 0.1827 0.039 Uiso calc R 1
C C16 0.22915(15) 0.4757(2) 0.35959(9) 0.0359(3) Uani d . 1
C C17 0.25322(17) 0.5307(2) 0.43643(9) 0.0433(4) Uani d . 1
H H17A 0.3316 0.4926 0.4633 0.065 Uiso calc R 1
H H17B 0.1945 0.4813 0.4579 0.065 Uiso calc R 1
H H17C 0.2493 0.6542 0.4385 0.065 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 0.0016 '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 106.63(11) y
C16 O3 C11 116.92(12) ?
C7 N1 C3 118.03(13) ?
C1 N2 N3 104.40(12) y
N2 N3 C2 111.64(12) y
N2 N3 C8 124.06(13) y
C2 N3 C8 124.02(13) y
N2 C1 O1 116.61(13) ?
N2 C1 C3 126.80(13) ?
O1 C1 C3 116.58(13) ?
N3 C2 C10 113.62(12) ?
N3 C2 O1 100.63(11) ?
C10 C2 O1 111.60(12) ?
N3 C2 H2 110.2 ?
C10 C2 H2 110.2 ?
O1 C2 H2 110.2 ?
N1 C3 C4 121.35(14) ?
N1 C3 C1 114.37(13) ?
C4 C3 C1 124.28(14) ?
C5 C4 C3 118.79(15) ?
C5 C4 Cl1 117.82(12) ?
C3 C4 Cl1 123.37(12) ?
C4 C5 C6 119.72(14) ?
C4 C5 H5 120.1 ?
C6 C5 H5 120.1 ?
C7 C6 C5 116.96(15) ?
C7 C6 H6 121.5 ?
C5 C6 H6 121.5 ?
N1 C7 C6 125.14(16) ?
N1 C7 Cl2 116.18(12) ?
C6 C7 Cl2 118.68(13) ?
O2 C8 N3 118.52(16) ?
O2 C8 C9 124.53(15) ?
N3 C8 C9 116.92(14) ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C15 C10 C11 117.93(14) ?
C15 C10 C2 119.36(13) ?
C11 C10 C2 122.71(13) ?
C12 C11 O3 119.06(14) ?
C12 C11 C10 121.94(14) ?
O3 C11 C10 118.90(13) ?
C11 C12 C13 119.23(15) ?
C11 C12 H12 120.4 ?
C13 C12 H12 120.4 ?
C14 C13 C12 119.99(15) ?
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 120.26(15) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C10 120.63(15) ?
C14 C15 H15 119.7 ?
C10 C15 H15 119.7 ?
O4 C16 O3 123.28(15) ?
O4 C16 C17 125.93(17) ?
O3 C16 C17 110.78(15) ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.7245(17) y
Cl2 C7 1.7423(18) y
O1 C1 1.3675(17) y
O1 C2 1.4414(17) y
O2 C8 1.218(2) y
O3 C16 1.373(2) y
O3 C11 1.4037(18) y
O4 C16 1.186(2) y
N1 C7 1.311(2) y
N1 C3 1.348(2) y
N2 C1 1.282(2) y
N2 N3 1.3871(17) y
N3 C8 1.363(2) y
N3 C2 1.4727(19) y
C1 C3 1.464(2) ?
C2 C10 1.510(2) ?
C2 H2 1.0000 ?
C3 C4 1.402(2) ?
C4 C5 1.387(2) ?
C5 C6 1.376(3) ?
C5 H5 0.9500 ?
C6 C7 1.390(2) ?
C6 H6 0.9500 ?
C8 C9 1.501(2) ?
C9 H9A 0.9800 ?
C9 H9B 0.9800 ?
C9 H9C 0.9800 ?
C10 C15 1.396(2) ?
C10 C11 1.391(2) ?
C11 C12 1.388(2) ?
C12 C13 1.386(2) ?
C12 H12 0.9500 ?
C13 C14 1.386(2) ?
C13 H13 0.9500 ?
C14 C15 1.392(2) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 C17 1.494(2) ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
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
C1 N2 N3 C8 -172.25(14)
C1 N2 N3 C2 1.86(16)
N3 N2 C1 O1 0.23(17)
N3 N2 C1 C3 -179.04(14)
C2 O1 C1 N2 -2.20(17)
C2 O1 C1 C3 177.13(12)
C8 N3 C2 C10 -69.50(18)
N2 N3 C2 C10 116.39(13)
C8 N3 C2 O1 171.11(13)
N2 N3 C2 O1 -3.00(15)
C1 O1 C2 N3 2.92(14)
C1 O1 C2 C10 -117.92(13)
C7 N1 C3 C4 0.4(2)
C7 N1 C3 C1 -179.35(13)
N2 C1 C3 N1 174.75(14)
O1 C1 C3 N1 -4.51(18)
N2 C1 C3 C4 -5.0(2)
O1 C1 C3 C4 175.74(13)
N1 C3 C4 C5 0.2(2)
C1 C3 C4 C5 179.89(14)
N1 C3 C4 Cl1 178.93(11)
C1 C3 C4 Cl1 -1.3(2)
C3 C4 C5 C6 -0.3(2)
Cl1 C4 C5 C6 -179.13(12)
C4 C5 C6 C7 -0.1(2)
C3 N1 C7 C6 -0.9(2)
C3 N1 C7 Cl2 178.95(11)
C5 C6 C7 N1 0.8(2)
C5 C6 C7 Cl2 -179.09(12)
N2 N3 C8 O2 171.01(14)
C2 N3 C8 O2 -2.4(2)
N2 N3 C8 C9 -11.0(2)
C2 N3 C8 C9 175.61(14)
N3 C2 C10 C15 125.63(15)
O1 C2 C10 C15 -121.44(15)
N3 C2 C10 C11 -54.91(19)
O1 C2 C10 C11 58.02(18)
C16 O3 C11 C12 -74.34(19)
C16 O3 C11 C10 109.06(16)
C15 C10 C11 C12 1.0(2)
C2 C10 C11 C12 -178.44(14)
C15 C10 C11 O3 177.53(13)
C2 C10 C11 O3 -1.9(2)
O3 C11 C12 C13 -177.96(15)
C10 C11 C12 C13 -1.5(2)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 0.4(3)
C13 C14 C15 C10 -0.8(3)
C11 C10 C15 C14 0.1(2)
C2 C10 C15 C14 179.61(14)
C11 O3 C16 O4 -2.4(2)
C11 O3 C16 C17 178.86(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13086836
