#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/36/2223625.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_2223625
loop_
_publ_author_name
'Manjare, Sudesh T.'
'Singh, Harkesh B.'
'Butcher, Ray J.'
_publ_section_title
;
 N-(2-Bromobenzyl)-N'-(2-pyridyl)benzene-1,2-diamine
;
_journal_coeditor_code           BT5071
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2640
_journal_paper_doi               10.1107/S1600536809039130
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H16 Br N3'
_chemical_formula_moiety         'C18 H16 Br N3'
_chemical_formula_sum            'C18 H16 Br N3'
_chemical_formula_weight         354.25
_chemical_name_systematic
;
N-(2-Bromobenzyl)-N'-(2-pyridyl)benzene-1,2-diamine
;
_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                98.741(6)
_cell_angle_beta                 90.727(6)
_cell_angle_gamma                103.581(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9429(5)
_cell_length_b                   9.5314(8)
_cell_length_c                   11.0606(8)
_cell_measurement_reflns_used    3047
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      34.7934
_cell_measurement_theta_min      4.6836
_cell_volume                     803.48(11)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8461
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.68
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular plate'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.483
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.052P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2038
_reflns_number_total             3249
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5071.cif
_cod_data_source_block           I
_cod_original_cell_volume        803.48(10)
_cod_database_code               2223625
_cod_database_fobs_code          2223625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.83487(5) 0.00876(4) 0.69232(3) 0.05856(16) Uani d . 1 . .
N N1 0.7358(3) 0.1251(3) 0.31573(19) 0.0433(6) Uani d . 1 . .
H H1A 0.6776 0.0542 0.2595 0.052 Uiso calc R 1 . .
N N2 0.5888(3) 0.1863(3) 0.1091(2) 0.0405(6) Uani d . 1 . .
H H2A 0.6118 0.1008 0.0849 0.049 Uiso calc R 1 . .
N N3 0.3381(3) 0.0980(2) -0.01114(19) 0.0326(5) Uani d . 1 . .
C C1 0.7931(4) 0.2636(3) 0.2846(2) 0.0351(7) Uani d . 1 . .
C C2 0.7198(4) 0.2970(3) 0.1804(2) 0.0348(7) Uani d . 1 . .
C C3 0.7745(4) 0.4348(3) 0.1484(3) 0.0408(7) Uani d . 1 . .
H H3A 0.7240 0.4563 0.0772 0.049 Uiso calc R 1 . .
C C4 0.9013(4) 0.5417(4) 0.2185(3) 0.0477(8) Uani d . 1 . .
H H4A 0.9353 0.6370 0.1975 0.057 Uiso calc R 1 . .
C C5 0.9773(4) 0.5079(4) 0.3189(3) 0.0481(9) Uani d . 1 . .
H H5A 1.0669 0.5799 0.3661 0.058 Uiso calc R 1 . .
C C6 0.9258(4) 0.3714(3) 0.3522(2) 0.0467(8) Uani d . 1 . .
H H6A 0.9807 0.3501 0.4217 0.056 Uiso calc R 1 . .
C C1A 0.7671(4) 0.0915(3) 0.4359(2) 0.0386(7) Uani d . 1 . .
H H1AA 0.8930 0.1249 0.4575 0.046 Uiso calc R 1 . .
H H1AB 0.7348 -0.0160 0.4317 0.046 Uiso calc R 1 . .
C C2A 0.6705(3) 0.1589(3) 0.5388(2) 0.0342(7) Uani d . 1 . .
C C3A 0.6902(4) 0.1324(3) 0.6583(2) 0.0384(7) Uani d . 1 . .
C C4A 0.6043(4) 0.1895(4) 0.7542(3) 0.0487(9) Uani d . 1 . .
H H4AA 0.6192 0.1680 0.8342 0.058 Uiso calc R 1 . .
C C5A 0.4973(5) 0.2775(4) 0.7325(3) 0.0563(10) Uani d . 1 . .
H H5AA 0.4387 0.3185 0.7981 0.068 Uiso calc R 1 . .
C C6A 0.4744(4) 0.3068(4) 0.6165(3) 0.0546(9) Uani d . 1 . .
H H6AA 0.3992 0.3672 0.6018 0.066 Uiso calc R 1 . .
C C7A 0.5616(4) 0.2476(3) 0.5202(3) 0.0441(8) Uani d . 1 . .
H H7AA 0.5456 0.2690 0.4403 0.053 Uiso calc R 1 . .
C C1B 0.4294(4) 0.2041(3) 0.0757(2) 0.0343(7) Uani d . 1 . .
C C2B 0.3615(4) 0.3199(3) 0.1284(3) 0.0434(8) Uani d . 1 . .
H H2BA 0.4278 0.3943 0.1892 0.052 Uiso calc R 1 . .
C C3B 0.1994(4) 0.3253(4) 0.0920(3) 0.0492(8) Uani d . 1 . .
H H3BA 0.1509 0.4029 0.1282 0.059 Uiso calc R 1 . .
C C4B 0.1052(4) 0.2177(4) 0.0020(3) 0.0495(8) Uani d . 1 . .
H H4BA -0.0076 0.2202 -0.0258 0.059 Uiso calc R 1 . .
C C5B 0.1800(4) 0.1081(4) -0.0453(3) 0.0416(7) Uani d . 1 . .
H H5BA 0.1155 0.0336 -0.1068 0.050 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C1A . . 123.2(2) ?
C1 N1 H1A . . 118.4 ?
C1A N1 H1A . . 118.4 ?
C1B N2 C2 . . 124.4(2) ?
C1B N2 H2A . . 117.8 ?
C2 N2 H2A . . 117.8 ?
C5B N3 C1B . . 117.5(2) ?
N1 C1 C2 . . 119.3(2) ?
N1 C1 C6 . . 122.5(3) ?
C2 C1 C6 . . 118.1(3) ?
C3 C2 C1 . . 120.1(2) ?
C3 C2 N2 . . 121.5(3) ?
C1 C2 N2 . . 118.4(3) ?
C4 C3 C2 . . 121.1(3) ?
C4 C3 H3A . . 119.5 ?
C2 C3 H3A . . 119.5 ?
C5 C4 C3 . . 118.9(3) ?
C5 C4 H4A . . 120.5 ?
C3 C4 H4A . . 120.5 ?
C4 C5 C6 . . 121.1(3) ?
C4 C5 H5A . . 119.4 ?
C6 C5 H5A . . 119.4 ?
C5 C6 C1 . . 120.6(3) ?
C5 C6 H6A . . 119.7 ?
C1 C6 H6A . . 119.7 ?
N1 C1A C2A . . 115.7(3) ?
N1 C1A H1AA . . 108.4 ?
C2A C1A H1AA . . 108.4 ?
N1 C1A H1AB . . 108.4 ?
C2A C1A H1AB . . 108.4 ?
H1AA C1A H1AB . . 107.4 ?
C7A C2A C3A . . 116.8(2) ?
C7A C2A C1A . . 122.8(3) ?
C3A C2A C1A . . 120.4(3) ?
C4A C3A C2A . . 122.6(3) ?
C4A C3A Br . . 117.6(2) ?
C2A C3A Br . . 119.8(2) ?
C5A C4A C3A . . 119.1(3) ?
C5A C4A H4AA . . 120.4 ?
C3A C4A H4AA . . 120.4 ?
C4A C5A C6A . . 120.3(3) ?
C4A C5A H5AA . . 119.9 ?
C6A C5A H5AA . . 119.9 ?
C5A C6A C7A . . 120.0(3) ?
C5A C6A H6AA . . 120.0 ?
C7A C6A H6AA . . 120.0 ?
C2A C7A C6A . . 121.3(3) ?
C2A C7A H7AA . . 119.4 ?
C6A C7A H7AA . . 119.4 ?
N3 C1B N2 . . 115.0(2) ?
N3 C1B C2B . . 121.4(3) ?
N2 C1B C2B . . 123.7(3) ?
C3B C2B C1B . . 119.3(3) ?
C3B C2B H2BA . . 120.4 ?
C1B C2B H2BA . . 120.4 ?
C2B C3B C4B . . 119.8(3) ?
C2B C3B H3BA . . 120.1 ?
C4B C3B H3BA . . 120.1 ?
C5B C4B C3B . . 117.5(3) ?
C5B C4B H4BA . . 121.2 ?
C3B C4B H4BA . . 121.2 ?
N3 C5B C4B . . 124.5(3) ?
N3 C5B H5BA . . 117.8 ?
C4B C5B H5BA . . 117.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br C3A . 1.900(3) ?
N1 C1 . 1.389(4) ?
N1 C1A . 1.446(3) ?
N1 H1A . 0.8800 ?
N2 C1B . 1.370(3) ?
N2 C2 . 1.423(3) ?
N2 H2A . 0.8800 ?
N3 C5B . 1.336(4) ?
N3 C1B . 1.347(3) ?
C1 C2 . 1.397(4) ?
C1 C6 . 1.401(4) ?
C2 C3 . 1.384(4) ?
C3 C4 . 1.383(4) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.372(4) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.377(4) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C1A C2A . 1.526(4) ?
C1A H1AA . 0.9900 ?
C1A H1AB . 0.9900 ?
C2A C7A . 1.377(4) ?
C2A C3A . 1.396(4) ?
C3A C4A . 1.380(4) ?
C4A C5A . 1.369(5) ?
C4A H4AA . 0.9500 ?
C5A C6A . 1.372(5) ?
C5A H5AA . 0.9500 ?
C6A C7A . 1.398(4) ?
C6A H6AA . 0.9500 ?
C7A H7AA . 0.9500 ?
C1B C2B . 1.393(4) ?
C2B C3B . 1.359(4) ?
C2B H2BA . 0.9500 ?
C3B C4B . 1.384(5) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.361(4) ?
C4B H4BA . 0.9500 ?
C5B H5BA . 0.9500 ?
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
N2 H2A N3 2_655 0.88 2.08 2.952(3) 174.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1A N1 C1 C2 . . . . -162.8(3) ?
C1A N1 C1 C6 . . . . 18.9(4) ?
N1 C1 C2 C3 . . . . 179.5(2) ?
C6 C1 C2 C3 . . . . -2.0(4) ?
N1 C1 C2 N2 . . . . -0.4(4) ?
C6 C1 C2 N2 . . . . 178.0(2) ?
C1B N2 C2 C3 . . . . -52.3(4) ?
C1B N2 C2 C1 . . . . 127.6(3) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
N2 C2 C3 C4 . . . . 179.7(3) ?
C2 C3 C4 C5 . . . . 2.1(4) ?
C3 C4 C5 C6 . . . . -1.8(5) ?
C4 C5 C6 C1 . . . . -0.4(5) ?
N1 C1 C6 C5 . . . . -179.3(3) ?
C2 C1 C6 C5 . . . . 2.3(4) ?
C1 N1 C1A C2A . . . . 68.9(3) ?
N1 C1A C2A C7A . . . . -0.8(4) ?
N1 C1A C2A C3A . . . . 179.4(2) ?
C7A C2A C3A C4A . . . . 0.9(4) ?
C1A C2A C3A C4A . . . . -179.3(3) ?
C7A C2A C3A Br . . . . 179.0(2) ?
C1A C2A C3A Br . . . . -1.2(3) ?
C2A C3A C4A C5A . . . . -1.0(5) ?
Br C3A C4A C5A . . . . -179.2(2) ?
C3A C4A C5A C6A . . . . 0.8(5) ?
C4A C5A C6A C7A . . . . -0.6(5) ?
C3A C2A C7A C6A . . . . -0.6(4) ?
C1A C2A C7A C6A . . . . 179.6(3) ?
C5A C6A C7A C2A . . . . 0.4(5) ?
C5B N3 C1B N2 . . . . 178.6(2) ?
C5B N3 C1B C2B . . . . 0.2(4) ?
C2 N2 C1B N3 . . . . 167.2(2) ?
C2 N2 C1B C2B . . . . -14.5(4) ?
N3 C1B C2B C3B . . . . 0.5(4) ?
N2 C1B C2B C3B . . . . -177.8(3) ?
C1B C2B C3B C4B . . . . -1.1(5) ?
C2B C3B C4B C5B . . . . 1.0(5) ?
C1B N3 C5B C4B . . . . -0.3(4) ?
C3B C4B C5B N3 . . . . -0.3(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743398
