#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151807.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_7151807
loop_
_publ_author_name
'Yella, Ramesh'
'Khatun, Nilufa'
'Rout, Saroj Kumar'
'Patel, Bhisma K.'
_publ_section_title
;
 Tandem regioselective synthesis of tetrazoles and related heterocycles
 using iodine.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3235
_journal_page_last               3245
_journal_paper_doi               10.1039/c0ob01007c
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C14 H13 N5 O'
_chemical_formula_sum            'C14 H13 N5 O'
_chemical_formula_weight         267.29
_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                 107.280(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8360(4)
_cell_length_b                   16.3772(6)
_cell_length_c                   7.6105(3)
_cell_measurement_reflns_used    5051
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1289.63(9)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15943
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0442
_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)+(0.0828P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                1965
_reflns_number_total             3221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01007c.txt
_cod_data_source_block           9b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151807
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14403(10) 0.21400(6) 0.41774(16) 0.0509(3) Uani 1 1 d . . .
N5 N 0.34812(10) 0.14928(7) 0.54249(16) 0.0540(3) Uani 1 1 d . . .
N2 N 0.10122(13) 0.29273(7) 0.38491(19) 0.0695(4) Uani 1 1 d . . .
N4 N 0.31189(12) 0.29338(7) 0.50218(18) 0.0655(4) Uani 1 1 d . . .
N3 N 0.20196(13) 0.33790(7) 0.4351(2) 0.0778(4) Uani 1 1 d . . .
O1 O 0.44775(8) 0.01767(5) 0.72129(13) 0.0605(3) Uani 1 1 d . . .
C1 C 0.05379(12) 0.14774(7) 0.37641(17) 0.0472(3) Uani 1 1 d . . .
C8 C 0.48251(12) 0.14871(7) 0.62733(17) 0.0474(3) Uani 1 1 d . . .
C7 C 0.27330(12) 0.21652(7) 0.49040(17) 0.0480(3) Uani 1 1 d . . .
C13 C 0.53501(11) 0.07797(8) 0.72312(17) 0.0493(3) Uani 1 1 d . . .
C6 C 0.07191(13) 0.08333(8) 0.27057(18) 0.0557(3) Uani 1 1 d . . .
H6 H 0.1438 0.0815 0.2277 0.067 Uiso 1 1 calc R . .
C9 C 0.56437(14) 0.21213(8) 0.6142(2) 0.0601(4) Uani 1 1 d . . .
H9 H 0.5308 0.2585 0.5464 0.072 Uiso 1 1 calc R . .
C4 C -0.12580(14) 0.02448(9) 0.28959(19) 0.0619(4) Uani 1 1 d . . .
H4 H -0.1874 -0.0168 0.2587 0.074 Uiso 1 1 calc R . .
C12 C 0.66627(13) 0.07381(10) 0.8109(2) 0.0650(4) Uani 1 1 d . . .
H12 H 0.7014 0.0272 0.8766 0.078 Uiso 1 1 calc R . .
C5 C -0.01893(15) 0.02120(8) 0.22902(19) 0.0619(4) Uani 1 1 d . . .
H5 H -0.0072 -0.0231 0.1593 0.074 Uiso 1 1 calc R . .
C14 C 0.49804(15) -0.06004(8) 0.7972(2) 0.0668(4) Uani 1 1 d . . .
H14A H 0.5543 -0.0811 0.7316 0.100 Uiso 1 1 calc R . .
H14B H 0.4279 -0.0974 0.7861 0.100 Uiso 1 1 calc R . .
H14C H 0.5455 -0.0535 0.9248 0.100 Uiso 1 1 calc R . .
C2 C -0.05197(12) 0.15046(8) 0.44172(19) 0.0580(4) Uani 1 1 d . . .
H2 H -0.0624 0.1935 0.5158 0.070 Uiso 1 1 calc R . .
C3 C -0.14175(13) 0.08883(9) 0.3960(2) 0.0648(4) Uani 1 1 d . . .
H3 H -0.2142 0.0908 0.4377 0.078 Uiso 1 1 calc R . .
C10 C 0.69493(15) 0.20648(10) 0.7013(3) 0.0716(4) Uani 1 1 d . . .
H10 H 0.7493 0.2492 0.6920 0.086 Uiso 1 1 calc R . .
C11 C 0.74542(14) 0.13849(11) 0.8013(2) 0.0748(5) Uani 1 1 d . . .
H11 H 0.8334 0.1359 0.8631 0.090 Uiso 1 1 calc R . .
H5N H 0.3073(14) 0.1060(10) 0.549(2) 0.072(5) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 107.54(10) . . ?
C7 N1 C1 132.33(9) . . ?
N2 N1 C1 120.12(10) . . ?
C7 N5 C8 125.98(11) . . ?
N3 N2 N1 106.11(11) . . ?
C7 N4 N3 105.13(11) . . ?
N2 N3 N4 112.12(11) . . ?
C13 O1 C14 117.27(10) . . ?
C6 C1 C2 120.95(12) . . ?
C6 C1 N1 120.17(12) . . ?
C2 C1 N1 118.87(11) . . ?
C9 C8 C13 119.21(12) . . ?
C9 C8 N5 123.94(12) . . ?
C13 C8 N5 116.78(11) . . ?
N4 C7 N1 109.10(10) . . ?
N4 C7 N5 127.20(12) . . ?
N1 C7 N5 123.70(11) . . ?
O1 C13 C12 125.45(12) . . ?
O1 C13 C8 114.93(10) . . ?
C12 C13 C8 119.62(12) . . ?
C1 C6 C5 118.76(12) . . ?
C10 C9 C8 120.17(14) . . ?
C5 C4 C3 119.78(13) . . ?
C11 C12 C13 120.26(14) . . ?
C4 C5 C6 120.61(13) . . ?
C3 C2 C1 119.15(12) . . ?
C4 C3 C2 120.71(13) . . ?
C11 C10 C9 120.46(14) . . ?
C10 C11 C12 120.17(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.3451(17) . ?
N1 N2 1.3680(14) . ?
N1 C1 1.4318(15) . ?
N5 C7 1.3551(15) . ?
N5 C8 1.4068(17) . ?
N2 N3 1.2794(17) . ?
N4 C7 1.3210(15) . ?
N4 N3 1.3603(17) . ?
O1 C13 1.3645(15) . ?
O1 C14 1.4365(15) . ?
C1 C6 1.3763(17) . ?
C1 C2 1.3787(18) . ?
C8 C9 1.3886(18) . ?
C8 C13 1.3969(17) . ?
C13 C12 1.3819(18) . ?
C6 C5 1.3853(18) . ?
C9 C10 1.376(2) . ?
C4 C5 1.369(2) . ?
C4 C3 1.371(2) . ?
C12 C11 1.378(2) . ?
C2 C3 1.3730(18) . ?
C10 C11 1.368(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26995691
2 PubChem 53382051
