#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/36/2213648.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_2213648
loop_
_publ_author_name
'Rui-Dian Ma'
'Bao-Lei Wang'
'Zheng-Ming Li'
'Hai-Bin Song'
_publ_section_title
;
 Ethyl 2-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]propanoate
;
_journal_coeditor_code           AT2286
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2897
_journal_page_last               o2897
_journal_paper_doi               10.1107/S160053680702168X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H16 N2 O4'
_chemical_formula_moiety         'C14 H16 N2 O4'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.29
_chemical_name_systematic
;
Ethyl 2-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]propanoate
;
_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                 91.190(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7947(15)
_cell_length_b                   7.8792(5)
_cell_length_c                   10.8786(12)
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     1353.5(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13948
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0485
_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)+(0.0589P)²+0.2367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                2314
_reflns_number_total             2672
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2286.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213648
_cod_database_fobs_code          2213648
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
O O1 0.41602(7) 0.58798(14) 0.23101(10) 0.0254(3) Uani d . 1
O O2 0.77137(7) 0.62012(14) -0.04248(10) 0.0258(3) Uani d . 1
O O3 0.87322(8) 0.71131(15) 0.15754(11) 0.0326(3) Uani d . 1
O O4 0.90040(7) 0.43446(14) 0.19355(10) 0.0265(3) Uani d . 1
N N1 0.38260(9) 0.78071(19) 0.09044(13) 0.0287(4) Uani d . 1
N N2 0.30974(9) 0.74429(19) 0.15997(13) 0.0285(4) Uani d . 1
C C1 0.44251(10) 0.6862(2) 0.13514(14) 0.0234(4) Uani d . 1
C C2 0.33238(10) 0.6316(2) 0.23984(15) 0.0258(4) Uani d . 1
C C3 0.28137(11) 0.5489(2) 0.33429(16) 0.0326(4) Uani d . 1
H H3A 0.3095 0.5619 0.4149 0.049 Uiso calc R 1
H H3B 0.2753 0.4280 0.3150 0.049 Uiso calc R 1
H H3C 0.2252 0.6018 0.3359 0.049 Uiso calc R 1
C C4 0.52943(10) 0.6709(2) 0.09470(14) 0.0228(4) Uani d . 1
C C5 0.55561(11) 0.7610(2) -0.00833(15) 0.0266(4) Uani d . 1
H H5 0.5173 0.8355 -0.0497 0.032 Uiso calc R 1
C C6 0.63673(11) 0.7423(2) -0.05021(15) 0.0268(4) Uani d . 1
H H6 0.6541 0.8040 -0.1203 0.032 Uiso calc R 1
C C7 0.69356(10) 0.6328(2) 0.00992(14) 0.0223(4) Uani d . 1
C C8 0.66890(10) 0.5461(2) 0.11445(15) 0.0242(4) Uani d . 1
H H8 0.7079 0.4746 0.1573 0.029 Uiso calc R 1
C C9 0.58680(10) 0.5646(2) 0.15578(15) 0.0235(4) Uani d . 1
H H9 0.5696 0.5041 0.2265 0.028 Uiso calc R 1
C C10 0.82978(10) 0.4994(2) 0.00736(15) 0.0246(4) Uani d . 1
H H10 0.8006 0.3886 0.0212 0.030 Uiso calc R 1
C C11 0.89808(11) 0.4781(2) -0.08708(16) 0.0313(4) Uani d . 1
H H11A 0.8729 0.4329 -0.1634 0.047 Uiso calc R 1
H H11B 0.9413 0.3991 -0.0555 0.047 Uiso calc R 1
H H11C 0.9242 0.5884 -0.1034 0.047 Uiso calc R 1
C C12 0.86873(10) 0.5645(2) 0.12807(15) 0.0237(4) Uani d . 1
C C13 0.94262(11) 0.4775(2) 0.31044(15) 0.0284(4) Uani d . 1
H H13A 0.9739 0.5855 0.3016 0.034 Uiso calc R 1
H H13B 0.9840 0.3876 0.3328 0.034 Uiso calc R 1
C C14 0.87892(11) 0.4950(2) 0.41083(16) 0.0312(4) Uani d . 1
H H14A 0.9087 0.5080 0.4902 0.047 Uiso calc R 1
H H14B 0.8432 0.3933 0.4126 0.047 Uiso calc R 1
H H14C 0.8435 0.5950 0.3949 0.047 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'
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
C2 O1 C1 102.80(13)
C7 O2 C10 118.05(12)
C12 O4 C13 116.32(13)
C1 N1 N2 106.17(14)
C2 N2 N1 106.39(13)
N1 C1 O1 112.28(15)
N1 C1 C4 128.48(15)
O1 C1 C4 119.21(14)
N2 C2 O1 112.35(15)
N2 C2 C3 128.93(16)
O1 C2 C3 118.73(15)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C9 C4 C5 119.22(15)
C9 C4 C1 120.93(15)
C5 C4 C1 119.84(14)
C6 C5 C4 120.28(15)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 120.30(15)
C5 C6 H6 119.9
C7 C6 H6 119.9
O2 C7 C8 125.03(14)
O2 C7 C6 115.07(14)
C8 C7 C6 119.89(15)
C9 C8 C7 119.51(15)
C9 C8 H8 120.2
C7 C8 H8 120.2
C8 C9 C4 120.75(15)
C8 C9 H9 119.6
C4 C9 H9 119.6
O2 C10 C11 106.30(13)
O2 C10 C12 110.42(13)
C11 C10 C12 109.92(13)
O2 C10 H10 110.0
C11 C10 H10 110.0
C12 C10 H10 110.0
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O3 C12 O4 125.11(15)
O3 C12 C10 124.98(15)
O4 C12 C10 109.85(14)
O4 C13 C14 110.61(14)
O4 C13 H13A 109.5
C14 C13 H13A 109.5
O4 C13 H13B 109.5
C14 C13 H13B 109.5
H13A C13 H13B 108.1
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3704(19)
O1 C1 1.3710(19)
O2 C7 1.3691(19)
O2 C10 1.4246(19)
O3 C12 1.202(2)
O4 C12 1.3391(19)
O4 C13 1.4633(19)
N1 C1 1.291(2)
N1 N2 1.419(2)
N2 C2 1.288(2)
C1 C4 1.455(2)
C2 C3 1.471(2)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 C9 1.393(2)
C4 C5 1.396(2)
C5 C6 1.377(2)
C5 H5 0.9500
C6 C7 1.397(2)
C6 H6 0.9500
C7 C8 1.389(2)
C8 C9 1.389(2)
C8 H8 0.9500
C9 H9 0.9500
C10 C11 1.514(2)
C10 C12 1.527(2)
C10 H10 1.0000
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C13 C14 1.506(2)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
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
C3 H3A N1 4_576 0.98 2.53 3.455(2) 156
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 N1 N2 C2 0.00(17)
N2 N1 C1 O1 -0.33(18)
N2 N1 C1 C4 178.06(15)
C2 O1 C1 N1 0.51(17)
C2 O1 C1 C4 -178.05(13)
N1 N2 C2 O1 0.32(18)
N1 N2 C2 C3 -179.63(16)
C1 O1 C2 N2 -0.50(17)
C1 O1 C2 C3 179.46(14)
N1 C1 C4 C9 178.51(16)
O1 C1 C4 C9 -3.2(2)
N1 C1 C4 C5 -2.9(3)
O1 C1 C4 C5 175.41(14)
C9 C4 C5 C6 1.2(2)
C1 C4 C5 C6 -177.42(15)
C4 C5 C6 C7 0.1(2)
C10 O2 C7 C8 5.2(2)
C10 O2 C7 C6 -174.42(14)
C5 C6 C7 O2 177.83(14)
C5 C6 C7 C8 -1.8(2)
O2 C7 C8 C9 -177.37(14)
C6 C7 C8 C9 2.2(2)
C7 C8 C9 C4 -0.9(2)
C5 C4 C9 C8 -0.8(2)
C1 C4 C9 C8 177.84(14)
C7 O2 C10 C11 164.65(13)
C7 O2 C10 C12 -76.17(17)
C13 O4 C12 O3 0.7(2)
C13 O4 C12 C10 178.02(12)
O2 C10 C12 O3 -23.0(2)
C11 C10 C12 O3 94.0(2)
O2 C10 C12 O4 159.74(13)
C11 C10 C12 O4 -83.30(17)
C12 O4 C13 C14 83.97(17)
