#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151806.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_7151806
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         'C13 H9 Cl2 N5'
_chemical_formula_sum            'C13 H9 Cl2 N5'
_chemical_formula_weight         306.15
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                81.772(2)
_cell_angle_beta                 70.996(2)
_cell_angle_gamma                76.860(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3229(2)
_cell_length_b                   9.8303(3)
_cell_length_c                   10.1610(3)
_cell_measurement_reflns_used    5469
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.90
_cell_volume                     671.58(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0704
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9197
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.050(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   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0573P)²+0.1167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2756
_reflns_number_total             3341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01007c.txt
_cod_data_source_block           7b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               7151806
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.12069(8) 0.54198(5) 0.27397(6) 0.06821(19) Uani 1 1 d . . .
Cl2 Cl 0.33696(7) 1.13966(6) 0.29135(6) 0.06812(19) Uani 1 1 d . . .
N1 N 0.98776(17) 0.81415(12) 0.12742(14) 0.0417(3) Uani 1 1 d . . .
N5 N 0.7384(2) 0.97929(14) 0.26915(15) 0.0470(3) Uani 1 1 d . . .
N2 N 1.18322(19) 0.80500(15) 0.05335(16) 0.0534(4) Uani 1 1 d . . .
N4 N 1.0765(2) 0.99979(14) 0.16024(16) 0.0511(3) Uani 1 1 d . . .
N3 N 1.2319(2) 0.91522(16) 0.07557(18) 0.0570(4) Uani 1 1 d . . .
C6 C 0.8853(2) 0.70545(14) 0.13092(15) 0.0382(3) Uani 1 1 d . . .
C1 C 0.9393(2) 0.57330(15) 0.19316(16) 0.0425(3) Uani 1 1 d . . .
C8 C 0.6782(2) 1.09175(14) 0.35509(15) 0.0415(3) Uani 1 1 d . . .
C5 C 0.7340(2) 0.73168(16) 0.07234(17) 0.0466(4) Uani 1 1 d . . .
H5 H 0.6975 0.8202 0.0314 0.056 Uiso 1 1 calc R . .
C7 C 0.9269(2) 0.93532(14) 0.19026(16) 0.0401(3) Uani 1 1 d . . .
C9 C 0.4901(2) 1.17284(16) 0.37719(16) 0.0462(4) Uani 1 1 d . . .
C3 C 0.6948(3) 0.49314(18) 0.13297(19) 0.0546(4) Uani 1 1 d . . .
H3 H 0.6311 0.4215 0.1324 0.066 Uiso 1 1 calc R . .
C4 C 0.6368(2) 0.62500(19) 0.07503(19) 0.0533(4) Uani 1 1 d . . .
H4 H 0.5327 0.6424 0.0378 0.064 Uiso 1 1 calc R . .
C2 C 0.8456(3) 0.46602(16) 0.19157(18) 0.0514(4) Uani 1 1 d . . .
H2 H 0.8843 0.3766 0.2298 0.062 Uiso 1 1 calc R . .
C10 C 0.4225(3) 1.27904(19) 0.4678(2) 0.0619(5) Uani 1 1 d . . .
H10 H 0.2961 1.3322 0.4822 0.074 Uiso 1 1 calc R . .
C13 C 0.7987(3) 1.11988(19) 0.4244(2) 0.0570(4) Uani 1 1 d . . .
H13 H 0.9252 1.0670 0.4106 0.068 Uiso 1 1 calc R . .
C12 C 0.7313(4) 1.2264(2) 0.5142(2) 0.0688(5) Uani 1 1 d . . .
H12 H 0.8130 1.2449 0.5601 0.083 Uiso 1 1 calc R . .
C11 C 0.5437(4) 1.3052(2) 0.5360(2) 0.0710(6) Uani 1 1 d . . .
H11 H 0.4991 1.3761 0.5969 0.085 Uiso 1 1 calc R . .
H1N H 0.651(3) 0.946(2) 0.263(2) 0.058(6) 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'
Cl Cl 0.1484 0.1585 '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 107.59(12) . . ?
C7 N1 C6 130.99(12) . . ?
N2 N1 C6 121.40(11) . . ?
C7 N5 C8 124.01(13) . . ?
N3 N2 N1 106.02(12) . . ?
C7 N4 N3 105.39(12) . . ?
N2 N3 N4 111.86(13) . . ?
C5 C6 C1 120.31(13) . . ?
C5 C6 N1 119.95(13) . . ?
C1 C6 N1 119.74(13) . . ?
C2 C1 C6 119.85(15) . . ?
C2 C1 Cl1 119.61(12) . . ?
C6 C1 Cl1 120.55(11) . . ?
C13 C8 C9 118.69(14) . . ?
C13 C8 N5 121.55(15) . . ?
C9 C8 N5 119.68(14) . . ?
C6 C5 C4 119.50(15) . . ?
N4 C7 N1 109.12(13) . . ?
N4 C7 N5 127.83(13) . . ?
N1 C7 N5 123.04(13) . . ?
C10 C9 C8 120.98(16) . . ?
C10 C9 Cl2 119.55(14) . . ?
C8 C9 Cl2 119.47(11) . . ?
C2 C3 C4 120.91(14) . . ?
C3 C4 C5 119.97(16) . . ?
C3 C2 C1 119.41(15) . . ?
C11 C10 C9 119.55(18) . . ?
C12 C13 C8 120.20(18) . . ?
C11 C12 C13 120.47(19) . . ?
C10 C11 C12 120.11(16) . . ?
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
Cl1 C1 1.7281(16) . ?
Cl2 C9 1.7347(18) . ?
N1 C7 1.3476(17) . ?
N1 N2 1.3720(17) . ?
N1 C6 1.4290(17) . ?
N5 C7 1.357(2) . ?
N5 C8 1.4082(18) . ?
N2 N3 1.2846(19) . ?
N4 C7 1.3183(19) . ?
N4 N3 1.365(2) . ?
C6 C5 1.380(2) . ?
C6 C1 1.392(2) . ?
C1 C2 1.387(2) . ?
C8 C13 1.387(2) . ?
C8 C9 1.391(2) . ?
C5 C4 1.388(2) . ?
C9 C10 1.388(2) . ?
C3 C2 1.376(3) . ?
C3 C4 1.379(3) . ?
C10 C11 1.374(3) . ?
C13 C12 1.384(2) . ?
C12 C11 1.380(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653485
2 PubChem 53381978
