#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/59/2215961.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215961
loop_
_publ_author_name
'Jian Wu'
_publ_section_title
;
 N-(6-Bromopyridin-2-yl)pyridin-2-amine
;
_journal_coeditor_code           HB2598
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4413
_journal_page_last               o4413
_journal_paper_doi               10.1107/S1600536807051860
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H8 Br N3'
_chemical_formula_moiety         'C10 H8 Br N3'
_chemical_formula_sum            'C10 H8 Br N3'
_chemical_formula_weight         250.10
_chemical_name_systematic
;
N-(6-Bromopyridin-2-yl)pyridin-2-amine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.299(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.177(7)
_cell_length_b                   7.551(2)
_cell_length_c                   12.293(4)
_cell_measurement_reflns_used    1723
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      1.95
_cell_volume                     1942.9(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5705
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.95
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.191
_exptl_absorpt_correction_T_max  0.503
_exptl_absorpt_correction_T_min  0.376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.445
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0325
_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)+(0.0456P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                1403
_reflns_number_total             1723
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2598.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2215961
_cod_database_fobs_code          2215961
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.348533(14) 0.03734(6) 0.56958(3) 0.06353(18) Uani d . 1
C C1 0.41493(12) 0.1357(4) 0.5224(2) 0.0404(6) Uani d . 1
C C2 0.41213(13) 0.1193(4) 0.4089(2) 0.0450(7) Uani d . 1
H H2 0.3782 0.0637 0.3537 0.054 Uiso calc R 1
C C3 0.46233(13) 0.1898(4) 0.3832(2) 0.0475(7) Uani d . 1
H H3 0.4623 0.1853 0.3076 0.057 Uiso calc R 1
C C4 0.51341(13) 0.2679(4) 0.4666(2) 0.0431(7) Uani d . 1
H H4 0.5476 0.3156 0.4485 0.052 Uiso calc R 1
C C5 0.51153(11) 0.2723(4) 0.5782(2) 0.0367(6) Uani d . 1
C C6 0.61548(12) 0.4275(4) 0.6853(2) 0.0381(6) Uani d . 1
C C7 0.64667(14) 0.5036(4) 0.7932(2) 0.0449(7) Uani d . 1
H H7 0.6301 0.4932 0.8533 0.054 Uiso calc R 1
C C8 0.69133(15) 0.5299(4) 0.6151(3) 0.0526(8) Uani d . 1
H H8 0.7069 0.5397 0.5538 0.063 Uiso calc R 1
C C9 0.72529(13) 0.6080(5) 0.7165(3) 0.0525(8) Uani d . 1
H H9 0.7629 0.6692 0.7241 0.063 Uiso calc R 1
C C10 0.70248(13) 0.5941(5) 0.8077(3) 0.0510(8) Uani d . 1
H H10 0.7247 0.6455 0.8784 0.061 Uiso calc R 1
N N1 0.46154(9) 0.2106(3) 0.60504(16) 0.0381(5) Uani d . 1
N N2 0.63662(11) 0.4391(3) 0.5976(2) 0.0465(6) Uani d . 1
N N3 0.55897(10) 0.3372(3) 0.67403(17) 0.0438(6) Uani d . 1
H H3A 0.5523 0.3185 0.7382 0.053 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0490(2) 0.0850(3) 0.0585(3) -0.02186(15) 0.02024(17) -0.00919(16)
C1 0.0378(13) 0.0412(18) 0.0436(15) 0.0047(12) 0.0153(12) 0.0020(12)
C2 0.0442(15) 0.0518(19) 0.0350(14) 0.0043(13) 0.0077(12) -0.0079(13)
C3 0.0497(16) 0.062(2) 0.0308(13) 0.0095(14) 0.0126(12) -0.0004(13)
C4 0.0457(14) 0.0493(19) 0.0388(14) 0.0059(12) 0.0200(13) 0.0036(13)
C5 0.0344(13) 0.0395(16) 0.0353(13) 0.0053(11) 0.0103(11) 0.0022(12)
C6 0.0332(13) 0.0424(18) 0.0376(14) 0.0059(11) 0.0103(11) 0.0052(12)
C7 0.0426(15) 0.053(2) 0.0386(15) 0.0000(12) 0.0128(13) 0.0025(13)
C8 0.0430(16) 0.070(2) 0.0493(17) -0.0016(14) 0.0218(14) 0.0038(16)
C9 0.0371(14) 0.058(2) 0.0602(19) -0.0044(14) 0.0131(14) 0.0058(16)
C10 0.0442(16) 0.056(2) 0.0454(16) -0.0016(14) 0.0054(13) -0.0014(14)
N1 0.0370(11) 0.0448(14) 0.0325(11) 0.0009(10) 0.0113(9) -0.0016(10)
N2 0.0411(13) 0.0582(19) 0.0439(13) -0.0025(11) 0.0189(11) -0.0007(11)
N3 0.0394(11) 0.0616(18) 0.0312(11) -0.0077(11) 0.0126(10) 0.0019(10)
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'
Br Br -0.2901 2.4595 '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
N1 C1 C2 125.5(3)
N1 C1 Br1 115.00(19)
C2 C1 Br1 119.5(2)
C3 C2 C1 115.6(3)
C3 C2 H2 122.2
C1 C2 H2 122.2
C2 C3 C4 121.8(3)
C2 C3 H3 119.1
C4 C3 H3 119.1
C3 C4 C5 117.3(3)
C3 C4 H4 121.4
C5 C4 H4 121.4
N1 C5 N3 111.8(2)
N1 C5 C4 122.2(2)
N3 C5 C4 126.0(2)
N2 C6 N3 120.3(2)
N2 C6 C7 123.5(3)
N3 C6 C7 116.2(2)
C10 C7 C6 117.9(3)
C10 C7 H7 121.0
C6 C7 H7 121.0
N2 C8 C9 124.3(3)
N2 C8 H8 117.8
C9 C8 H8 117.8
C8 C9 C10 118.1(3)
C8 C9 H9 120.9
C10 C9 H9 120.9
C7 C10 C9 119.4(3)
C7 C10 H10 120.3
C9 C10 H10 120.3
C1 N1 C5 117.6(2)
C6 N2 C8 116.7(2)
C5 N3 C6 131.6(2)
C5 N3 H3A 114.2
C6 N3 H3A 114.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.903(3)
C1 N1 1.314(3)
C1 C2 1.381(4)
C2 C3 1.362(4)
C2 H2 0.9300
C3 C4 1.384(4)
C3 H3 0.9300
C4 C5 1.387(4)
C4 H4 0.9300
C5 N1 1.340(3)
C5 N3 1.384(3)
C6 N2 1.313(4)
C6 N3 1.392(3)
C6 C7 1.401(4)
C7 C10 1.373(4)
C7 H7 0.9300
C8 N2 1.348(4)
C8 C9 1.359(5)
C8 H8 0.9300
C9 C10 1.378(4)
C9 H9 0.9300
C10 H10 0.9300
N3 H3A 0.8600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A N1 2_656 0.86 2.21 3.052(3) 168
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21121269
