#------------------------------------------------------------------------------
#$Date: 2022-05-05 12:18:58 +0300 (Thu, 05 May 2022) $
#$Revision: 274925 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105159.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_8105159
loop_
_publ_author_name
'Mou, Xiao-Dong'
'Xu, Yang-Rong'
'Liu, Li'
'Zhang, Xiao-Fan'
'Meng, Qing-Guo'
_publ_section_title
;
 The crystal structure of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine,
 C7H6BrN5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              521
_journal_page_last               522
_journal_paper_doi               10.1515/ncrs-2019-0732
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C7 H6 Br N5'
_chemical_formula_sum            'C7 H6 Br N5'
_chemical_formula_weight         240.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                107.213(5)
_cell_angle_beta                 99.394(4)
_cell_angle_gamma                95.540(4)
_cell_formula_units_Z            4
_cell_length_a                   8.3319(4)
_cell_length_b                   10.0666(5)
_cell_length_c                   11.4042(6)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1310
_cell_measurement_theta_min      3.8180
_cell_volume                     890.71(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -88.00  21.00   1.00    1.29    --  -11.63 -77.00-150.00  109
  2  ω    -16.00  85.00   1.00    1.29    --   11.71  57.00 120.00  101
  3  ω    -61.00  40.00   1.00    1.29    --   11.71 -57.00 -30.00  101
  4  ω   -100.00 -75.00   1.00    1.29    --  -11.63-178.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0855498000
_diffrn_orient_matrix_UB_12      -0.0256448000
_diffrn_orient_matrix_UB_13      -0.0197690000
_diffrn_orient_matrix_UB_21      -0.0012607000
_diffrn_orient_matrix_UB_22      -0.0120141000
_diffrn_orient_matrix_UB_23      0.0580936000
_diffrn_orient_matrix_UB_31      -0.0174770000
_diffrn_orient_matrix_UB_32      0.0690712000
_diffrn_orient_matrix_UB_33      0.0255701000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.566
_diffrn_reflns_theta_min         3.414
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0399P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2696
_reflns_number_total             4190
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0732_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105159
_chemical_oxdiff_formula         'C1 H1 N1 Br1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C10(H10), C11(H11), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.44510(5) 0.72468(3) 0.04301(4) 0.05319(15) Uani 1 1 d . . . . .
Br2 Br -0.28943(5) -0.00876(4) 0.28107(4) 0.06311(17) Uani 1 1 d . . . . .
C1 C 0.2354(4) 0.4913(3) 0.0550(3) 0.0401(8) Uani 1 1 d . . . . .
H1 H 0.2733 0.5332 0.1409 0.048 Uiso 1 1 calc R . . . .
C2 C 0.2927(4) 0.5550(3) -0.0250(3) 0.0359(8) Uani 1 1 d . . . . .
C3 C 0.2416(4) 0.4947(3) -0.1518(3) 0.0410(8) Uani 1 1 d . . . . .
H3 H 0.2811 0.5351 -0.2072 0.049 Uiso 1 1 calc R . . . .
C4 C 0.1303(4) 0.3729(3) -0.1947(3) 0.0409(8) Uani 1 1 d . . . . .
H4 H 0.0914 0.3296 -0.2803 0.049 Uiso 1 1 calc R . . . .
C5 C 0.0764(4) 0.3150(3) -0.1091(3) 0.0336(8) Uani 1 1 d . . . . .
C6 C -0.0449(4) 0.1867(3) -0.1516(3) 0.0344(8) Uani 1 1 d . . . . .
C7 C -0.2890(5) -0.0990(3) -0.1233(4) 0.0530(10) Uani 1 1 d . . . . .
H7A H -0.2119 -0.1495 -0.0892 0.079 Uiso 1 1 calc GR . . . .
H7B H -0.3637 -0.1630 -0.1955 0.079 Uiso 1 1 calc GR . . . .
H7C H -0.3499 -0.0561 -0.0613 0.079 Uiso 1 1 calc GR . . . .
C8 C -0.0390(5) 0.2006(3) 0.4522(3) 0.0465(9) Uani 1 1 d . . . . .
H8 H -0.0665 0.1557 0.5083 0.056 Uiso 1 1 calc R . . . .
C9 C -0.1221(4) 0.1491(3) 0.3300(3) 0.0385(8) Uani 1 1 d . . . . .
C10 C -0.0824(4) 0.2125(3) 0.2452(3) 0.0450(9) Uani 1 1 d . . . . .
H10 H -0.1361 0.1784 0.1616 0.054 Uiso 1 1 calc R . . . .
C11 C 0.0385(5) 0.3275(3) 0.2870(3) 0.0429(9) Uani 1 1 d . . . . .
H11 H 0.0682 0.3726 0.2317 0.051 Uiso 1 1 calc R . . . .
C12 C 0.1164(4) 0.3763(3) 0.4122(3) 0.0337(7) Uani 1 1 d . . . . .
C13 C 0.2456(4) 0.4988(3) 0.4608(3) 0.0345(8) Uani 1 1 d . . . . .
C14 C 0.5067(5) 0.7776(4) 0.4374(4) 0.0600(11) Uani 1 1 d . . . . .
H14A H 0.5730 0.8449 0.5121 0.090 Uiso 1 1 calc GR . . . .
H14B H 0.4344 0.8247 0.3947 0.090 Uiso 1 1 calc GR . . . .
H14C H 0.5767 0.7334 0.3835 0.090 Uiso 1 1 calc GR . . . .
N1 N 0.1292(3) 0.3736(3) 0.0155(2) 0.0387(7) Uani 1 1 d . . . . .
N2 N -0.0878(3) 0.1123(3) -0.0788(2) 0.0367(7) Uani 1 1 d . . . . .
N3 N -0.1997(3) 0.0108(3) -0.1599(3) 0.0385(7) Uani 1 1 d . . . . .
N4 N -0.2280(4) 0.0181(3) -0.2734(3) 0.0506(8) Uani 1 1 d . . . . .
N5 N -0.1306(4) 0.1302(3) -0.2713(3) 0.0497(8) Uani 1 1 d . . . . .
N6 N 0.0791(4) 0.3119(3) 0.4943(3) 0.0456(8) Uani 1 1 d . . . . .
N7 N 0.3303(4) 0.5504(3) 0.5798(3) 0.0437(7) Uani 1 1 d . . . . .
N8 N 0.4346(4) 0.6601(3) 0.5844(3) 0.0460(8) Uani 1 1 d . . . . .
N9 N 0.4088(3) 0.6704(3) 0.4711(3) 0.0408(7) Uani 1 1 d . . . . .
N10 N 0.2922(3) 0.5733(3) 0.3897(3) 0.0402(7) 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'
Br Br -0.2901 2.4595 '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'
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
C1 N1 C5 117.3(3) . .
N3 N2 C6 101.3(3) . .
N8 N9 N10 114.3(2) . .
N8 N9 C14 122.3(3) . .
N10 N9 C14 123.3(3) . .
N4 N5 C6 105.9(3) . .
N9 N8 N7 106.1(3) . .
N2 N3 C7 122.4(3) . .
N4 N3 N2 114.7(3) . .
N4 N3 C7 122.9(3) . .
N1 C1 C2 123.0(3) . .
N3 N4 N5 106.5(3) . .
C1 C2 Br1 119.2(2) . .
C3 C2 Br1 120.8(2) . .
C3 C2 C1 119.9(3) . .
C3 C4 C5 119.3(3) . .
N9 N10 C13 101.4(3) . .
N8 N7 C13 106.0(3) . .
C11 C10 C9 118.2(3) . .
C8 N6 C12 117.8(3) . .
C10 C9 Br2 121.1(3) . .
C8 C9 Br2 119.3(2) . .
C8 C9 C10 119.6(3) . .
C10 C11 C12 119.7(3) . .
N2 C6 N5 111.6(3) . .
N2 C6 C5 125.1(3) . .
N5 C6 C5 123.3(3) . .
N10 C13 N7 112.2(3) . .
N10 C13 C12 122.6(3) . .
N7 C13 C12 125.2(3) . .
N1 C5 C4 122.6(3) . .
N1 C5 C6 116.7(3) . .
C4 C5 C6 120.7(3) . .
N6 C12 C11 121.8(3) . .
N6 C12 C13 116.7(3) . .
C11 C12 C13 121.5(3) . .
C2 C3 C4 117.9(3) . .
N6 C8 C9 123.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.899(3) .
Br2 C9 1.891(3) .
N1 C1 1.319(4) .
N1 C5 1.346(4) .
N2 N3 1.321(3) .
N2 C6 1.339(4) .
N9 N8 1.311(4) .
N9 N10 1.322(4) .
N9 C14 1.468(4) .
N5 N4 1.316(4) .
N5 C6 1.356(4) .
N8 N7 1.320(4) .
N3 N4 1.303(4) .
N3 C7 1.471(4) .
C1 C2 1.380(4) .
C2 C3 1.368(5) .
C4 C5 1.387(4) .
C4 C3 1.371(4) .
N10 C13 1.333(4) .
N7 C13 1.345(4) .
C10 C9 1.372(4) .
C10 C11 1.368(4) .
N6 C12 1.344(4) .
N6 C8 1.330(4) .
C9 C8 1.371(5) .
C11 C12 1.386(5) .
C6 C5 1.463(4) .
C13 C12 1.460(4) .
