#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151704.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_7151704
loop_
_publ_author_name
'Smith, Catherine J.'
'Nikbin, Nikzad'
'Ley, Steven V.'
'Lange, Heiko'
'Baxendale, Ian R.'
_publ_section_title
;
 A fully automated, multistep flow synthesis of
 5-amino-4-cyano-1,2,3-triazoles.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1938
_journal_page_last               1947
_journal_paper_doi               10.1039/C0OB00815J
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C10 H5 Br N6'
_chemical_formula_sum            'C10 H5 Br N6'
_chemical_formula_weight         289.11
_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                97.305(1)
_cell_angle_beta                 110.101(1)
_cell_angle_gamma                90.585(1)
_cell_formula_units_Z            2
_cell_length_a                   7.2576(2)
_cell_length_b                   8.4262(2)
_cell_length_c                   8.8405(2)
_cell_measurement_reflns_used    5799
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     502.74(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9286
_diffrn_reflns_theta_full        32.02
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    4.072
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0320
_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)+(0.0374P)²+0.2488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                3053
_reflns_number_total             3475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00815J.TXT
_cod_data_source_block           sl1010
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151704
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
Br1 Br 0.02984(3) 0.32350(2) 0.31503(2) 0.02511(7) Uani 1 1 d . . .
N1 N -0.3249(2) 0.84892(17) -0.07837(18) 0.0195(3) Uani 1 1 d . . .
N2 N -0.2912(3) 1.01096(18) -0.0353(2) 0.0256(3) Uani 1 1 d . . .
N3 N -0.4130(3) 1.07523(19) -0.1549(2) 0.0253(3) Uani 1 1 d . . .
N4 N -0.7837(3) 1.0286(2) -0.5330(2) 0.0361(4) Uani 1 1 d . . .
N5 N -0.5284(2) 0.65817(18) -0.30058(18) 0.0206(3) Uani 1 1 d . . .
N6 N -0.4968(3) 0.39128(19) -0.2895(2) 0.0274(4) Uani 1 1 d . . .
H6A H -0.5835 0.3720 -0.3887 0.033 Uiso 1 1 calc R . .
H6B H -0.4442 0.3112 -0.2377 0.033 Uiso 1 1 calc R . .
C1 C -0.4687(3) 0.8092(2) -0.2269(2) 0.0192(3) Uani 1 1 d . . .
C2 C -0.5247(3) 0.9583(2) -0.2733(2) 0.0217(3) Uani 1 1 d . . .
C3 C -0.6702(3) 0.9953(2) -0.4175(2) 0.0253(4) Uani 1 1 d . . .
C4 C -0.2351(3) 0.7326(2) 0.0162(2) 0.0190(3) Uani 1 1 d . . .
C5 C -0.0912(3) 0.7726(2) 0.1704(2) 0.0227(3) Uani 1 1 d . . .
H5B H -0.0491 0.8814 0.2131 0.027 Uiso 1 1 calc R . .
C6 C -0.0115(3) 0.6508(2) 0.2595(2) 0.0230(3) Uani 1 1 d . . .
H6C H 0.0868 0.6752 0.3642 0.028 Uiso 1 1 calc R . .
C7 C -0.0765(3) 0.4915(2) 0.1945(2) 0.0200(3) Uani 1 1 d . . .
C8 C -0.2164(3) 0.4514(2) 0.0409(2) 0.0195(3) Uani 1 1 d . . .
H8A H -0.2565 0.3423 -0.0016 0.023 Uiso 1 1 calc R . .
C9 C -0.2983(3) 0.5734(2) -0.0517(2) 0.0176(3) Uani 1 1 d . . .
C10 C -0.4449(3) 0.5425(2) -0.2172(2) 0.0188(3) 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
_geom_angle_publ_flag
C1 N1 N2 112.23(14) . . ?
C1 N1 C4 121.53(15) . . ?
N2 N1 C4 126.17(15) . . ?
N3 N2 N1 106.07(15) . . ?
N2 N3 C2 110.10(15) . . ?
C10 N5 C1 116.15(15) . . ?
C10 N6 H6A 120.0 . . ?
C10 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N5 C1 N1 124.78(15) . . ?
N5 C1 C2 132.58(17) . . ?
N1 C1 C2 102.63(15) . . ?
N3 C2 C1 108.96(16) . . ?
N3 C2 C3 121.82(16) . . ?
C1 C2 C3 129.22(17) . . ?
N4 C3 C2 178.1(2) . . ?
N1 C4 C5 121.87(16) . . ?
N1 C4 C9 115.95(15) . . ?
C5 C4 C9 122.17(16) . . ?
C6 C5 C4 118.77(17) . . ?
C6 C5 H5B 120.6 . . ?
C4 C5 H5B 120.6 . . ?
C5 C6 C7 119.61(17) . . ?
C5 C6 H6C 120.2 . . ?
C7 C6 H6C 120.2 . . ?
C8 C7 C6 121.75(16) . . ?
C8 C7 Br1 118.02(13) . . ?
C6 C7 Br1 120.21(13) . . ?
C7 C8 C9 119.41(17) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C4 C9 C8 118.26(16) . . ?
C4 C9 C10 118.38(15) . . ?
C8 C9 C10 123.35(16) . . ?
N5 C10 N6 117.46(16) . . ?
N5 C10 C9 122.99(16) . . ?
N6 C10 C9 119.55(15) . . ?
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
Br1 C7 1.8910(17) . ?
N1 C1 1.365(2) . ?
N1 N2 1.366(2) . ?
N1 C4 1.390(2) . ?
N2 N3 1.306(2) . ?
N3 C2 1.365(2) . ?
N4 C3 1.140(3) . ?
N5 C10 1.322(2) . ?
N5 C1 1.347(2) . ?
N6 C10 1.338(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
C1 C2 1.393(2) . ?
C2 C3 1.421(3) . ?
C4 C5 1.400(2) . ?
C4 C9 1.401(2) . ?
C5 C6 1.383(3) . ?
C5 H5B 0.9500 . ?
C6 C7 1.400(3) . ?
C6 H6C 0.9500 . ?
C7 C8 1.385(2) . ?
C8 C9 1.404(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.473(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 0.3(2) . . . . ?
C4 N1 N2 N3 -176.66(18) . . . . ?
N1 N2 N3 C2 0.3(2) . . . . ?
C10 N5 C1 N1 2.9(3) . . . . ?
C10 N5 C1 C2 -178.2(2) . . . . ?
N2 N1 C1 N5 178.44(18) . . . . ?
C4 N1 C1 N5 -4.5(3) . . . . ?
N2 N1 C1 C2 -0.7(2) . . . . ?
C4 N1 C1 C2 176.40(17) . . . . ?
N2 N3 C2 C1 -0.8(2) . . . . ?
N2 N3 C2 C3 179.8(2) . . . . ?
N5 C1 C2 N3 -178.2(2) . . . . ?
N1 C1 C2 N3 0.8(2) . . . . ?
N5 C1 C2 C3 1.2(4) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
N3 C2 C3 N4 34(7) . . . . ?
C1 C2 C3 N4 -145(7) . . . . ?
C1 N1 C4 C5 -178.29(18) . . . . ?
N2 N1 C4 C5 -1.6(3) . . . . ?
C1 N1 C4 C9 1.2(3) . . . . ?
N2 N1 C4 C9 177.89(18) . . . . ?
N1 C4 C5 C6 178.41(18) . . . . ?
C9 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C5 C6 C7 Br1 -179.70(15) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
Br1 C7 C8 C9 179.96(14) . . . . ?
N1 C4 C9 C8 -178.16(16) . . . . ?
C5 C4 C9 C8 1.4(3) . . . . ?
N1 C4 C9 C10 2.8(3) . . . . ?
C5 C4 C9 C10 -177.68(18) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C7 C8 C9 C10 178.77(17) . . . . ?
C1 N5 C10 N6 -177.93(18) . . . . ?
C1 N5 C10 C9 1.5(3) . . . . ?
C4 C9 C10 N5 -4.4(3) . . . . ?
C8 C9 C10 N5 176.60(18) . . . . ?
C4 C9 C10 N6 175.02(19) . . . . ?
C8 C9 C10 N6 -4.0(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653468
2 PubChem 54752261
