#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:21:00 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244655 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239329.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_7239329
loop_
_publ_author_name
'Majji, Ganesh'
'Rout, Saroj Kumar'
'Guin, Srimanta'
'Gogoi, Anupal'
'Patel, Bhisma K.'
_publ_section_title
;
 Iodine-catalysed oxidative cyclisation of acylhydrazones to
 2,5-substituted 1,3,4-oxadiazoles
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              5357
_journal_paper_doi               10.1039/c3ra44897e
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C14 H16 N2 O '
_chemical_formula_sum            'C14 H16 N2 O'
_chemical_formula_weight         228.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.896(2)
_cell_angle_beta                 92.553(2)
_cell_angle_gamma                90.149(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7158(2)
_cell_length_b                   9.9633(4)
_cell_length_c                   11.1928(4)
_cell_measurement_temperature    298(2)
_cell_volume                     602.36(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6900
_diffrn_reflns_theta_full        29.59
_diffrn_reflns_theta_max         29.59
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2055
_reflns_number_total             3353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra44897e.txt
_cod_data_source_block           mg-1
_cod_database_code               7239329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C9 C -0.1099(2) 0.43364(12) 0.64235(11) 0.0417(3) Uani 1 1 d .
C8 C -0.1012(2) 0.33147(12) 0.51502(11) 0.0413(3) Uani 1 1 d .
C6 C 0.2191(2) 0.06742(12) 0.29496(10) 0.0425(3) Uani 1 1 d .
H6 H 0.3667 0.1200 0.3011 0.051 Uiso 1 1 calc R
C7 C 0.0411(2) 0.17025(12) 0.36038(11) 0.0417(3) Uani 1 1 d .
C5 C 0.2611(2) -0.04459(13) 0.36070(11) 0.0491(3) Uani 1 1 d .
H5A H 0.3085 0.0022 0.4488 0.059 Uiso 1 1 calc R
H5B H 0.1165 -0.0970 0.3576 0.059 Uiso 1 1 calc R
C14 C 0.0716(2) 0.44533(13) 0.73189(11) 0.0493(3) Uani 1 1 d .
H14 H 0.2028 0.3891 0.7107 0.059 Uiso 1 1 calc R
C10 C -0.3045(2) 0.51964(14) 0.67494(13) 0.0516(3) Uani 1 1 d .
H10 H -0.4264 0.5132 0.6154 0.062 Uiso 1 1 calc R
C3 C 0.3870(3) -0.21733(14) 0.15719(13) 0.0589(4) Uani 1 1 d .
H3A H 0.2484 -0.2771 0.1473 0.071 Uiso 1 1 calc R
H3B H 0.5144 -0.2772 0.1178 0.071 Uiso 1 1 calc R
C1 C 0.1532(3) -0.00435(14) 0.15495(11) 0.0522(3) Uani 1 1 d .
H1A H 0.0050 -0.0551 0.1461 0.063 Uiso 1 1 calc R
H1B H 0.1343 0.0672 0.1137 0.063 Uiso 1 1 calc R
C12 C -0.1369(3) 0.62438(14) 0.88400(13) 0.0607(4) Uani 1 1 d .
H12 H -0.1464 0.6880 0.9654 0.073 Uiso 1 1 calc R
C2 C 0.3411(3) -0.10736(14) 0.09146(12) 0.0596(4) Uani 1 1 d .
H2A H 0.4850 -0.0550 0.0929 0.072 Uiso 1 1 calc R
H2B H 0.2919 -0.1552 0.0038 0.072 Uiso 1 1 calc R
C4 C 0.4497(3) -0.14678(14) 0.29707(12) 0.0549(3) Uani 1 1 d .
H4A H 0.5977 -0.0956 0.3071 0.066 Uiso 1 1 calc R
H4B H 0.4681 -0.2189 0.3376 0.066 Uiso 1 1 calc R
C13 C 0.0576(3) 0.54037(15) 0.85255(13) 0.0582(4) Uani 1 1 d .
H13 H 0.1790 0.5478 0.9126 0.070 Uiso 1 1 calc R
C11 C -0.3160(3) 0.61424(14) 0.79550(13) 0.0594(4) Uani 1 1 d .
H11 H -0.4459 0.6716 0.8171 0.071 Uiso 1 1 calc R
N2 N -0.25967(19) 0.29994(12) 0.42447(10) 0.0557(3) Uani 1 1 d .
N1 N -0.16464(19) 0.19341(12) 0.32215(10) 0.0552(3) Uani 1 1 d .
O1 O 0.09547(13) 0.25372(8) 0.48229(7) 0.0428(2) Uani 1 1 d .
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
C14 C9 C10 119.40(11)
C14 C9 C8 121.00(10)
C10 C9 C8 119.60(11)
N2 C8 O1 112.11(10)
N2 C8 C9 128.93(11)
O1 C8 C9 118.95(10)
C7 C6 C1 112.49(10)
C7 C6 C5 110.68(9)
C1 C6 C5 110.28(10)
N1 C7 O1 112.26(10)
N1 C7 C6 130.27(11)
O1 C7 C6 117.46(10)
C4 C5 C6 110.87(10)
C13 C14 C9 120.09(12)
C11 C10 C9 119.92(13)
C4 C3 C2 111.14(11)
C2 C1 C6 110.74(11)
C11 C12 C13 120.19(12)
C1 C2 C3 111.62(10)
C3 C4 C5 111.09(11)
C14 C13 C12 119.99(13)
C12 C11 C10 120.41(13)
C8 N2 N1 106.37(10)
C7 N1 N2 106.28(10)
C8 O1 C7 102.98(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C14 1.3877(17)
C9 C10 1.3938(16)
C9 C8 1.4617(16)
C8 N2 1.2871(15)
C8 O1 1.3622(13)
C6 C7 1.4856(16)
C6 C1 1.5261(16)
C6 C5 1.5369(16)
C7 N1 1.2806(15)
C7 O1 1.3697(14)
C5 C4 1.5198(17)
C14 C13 1.3816(18)
C10 C11 1.3777(18)
C3 C4 1.5197(19)
C3 C2 1.5222(19)
C1 C2 1.5207(18)
C12 C11 1.373(2)
C12 C13 1.3814(19)
N2 N1 1.4157(15)
