#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/85/2228535.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_2228535
loop_
_publ_author_name
'Wang, Jun'
'Dai, Chuntao'
'Nie, Jianhua'
_publ_section_title
;
 N-Benzylpyridin-2-amine
;
_journal_coeditor_code           RZ2510
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3076
_journal_paper_doi               10.1107/S1600536810044478
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H12 N2'
_chemical_formula_moiety         'C12 H12 N2'
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24
_chemical_name_systematic
;
N-Benzylpyridin-2-amine
;
_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                95.471(4)
_cell_angle_beta                 91.244(4)
_cell_angle_gamma                94.779(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9014(16)
_cell_length_b                   8.025(2)
_cell_length_c                   10.561(3)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.23
_cell_volume                     495.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_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  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2551
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0419
_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)+(0.0576P)²+0.0854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                1387
_reflns_number_total             1762
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2510.cif
_cod_data_source_block           I
_cod_database_code               2228535
_cod_database_fobs_code          2228535
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
C C1 -0.1362(3) 0.24905(19) 0.36541(15) 0.0350(4) Uani d . 1 . .
H H1 -0.2427 0.1909 0.4122 0.042 Uiso calc R 1 . .
C C2 0.0725(3) 0.30933(18) 0.42172(14) 0.0308(4) Uani d . 1 . .
C C3 0.2280(3) 0.39773(19) 0.34991(15) 0.0357(4) Uani d . 1 . .
H H3 0.3689 0.4396 0.3860 0.043 Uiso calc R 1 . .
C C4 0.1748(3) 0.4236(2) 0.22596(16) 0.0397(4) Uani d . 1 . .
H H4 0.2798 0.4832 0.1793 0.048 Uiso calc R 1 . .
C C5 -0.0331(3) 0.3616(2) 0.17061(16) 0.0408(4) Uani d . 1 . .
H H5 -0.0680 0.3788 0.0868 0.049 Uiso calc R 1 . .
C C6 -0.1889(3) 0.2740(2) 0.24050(16) 0.0403(4) Uani d . 1 . .
H H6 -0.3292 0.2317 0.2038 0.048 Uiso calc R 1 . .
C C7 0.1283(3) 0.2820(2) 0.55703(15) 0.0359(4) Uani d . 1 . .
H H7A 0.1617 0.3897 0.6065 0.043 Uiso calc R 1 . .
H H7B -0.0022 0.2242 0.5932 0.043 Uiso calc R 1 . .
C C8 0.4265(3) 0.15939(18) 0.67594(14) 0.0301(4) Uani d . 1 . .
C C9 0.3600(3) 0.23242(19) 0.79450(14) 0.0353(4) Uani d . 1 . .
H H9 0.2360 0.2968 0.7998 0.042 Uiso calc R 1 . .
C C10 0.4814(3) 0.2067(2) 0.90146(15) 0.0412(4) Uani d . 1 . .
H H10 0.4406 0.2545 0.9805 0.049 Uiso calc R 1 . .
C C11 0.6648(3) 0.1099(2) 0.89304(15) 0.0397(4) Uani d . 1 . .
H H11 0.7507 0.0930 0.9649 0.048 Uiso calc R 1 . .
C C12 0.7150(3) 0.03973(19) 0.77449(15) 0.0359(4) Uani d . 1 . .
H H12 0.8367 -0.0269 0.7683 0.043 Uiso calc R 1 . .
N N1 0.6010(2) 0.06064(16) 0.66736(12) 0.0334(3) Uani d . 1 . .
N N2 0.3221(2) 0.18353(16) 0.56430(12) 0.0355(3) Uani d . 1 . .
H H2 0.3734 0.1384 0.4947 0.043 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'
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
C2 C1 C6 . . 121.05(15) ?
C2 C1 H1 . . 119.5 ?
C6 C1 H1 . . 119.5 ?
C1 C2 C3 . . 118.30(14) ?
C1 C2 C7 . . 120.76(14) ?
C3 C2 C7 . . 120.94(14) ?
C4 C3 C2 . . 120.63(15) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.50(16) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 119.57(15) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 119.96(15) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
N2 C7 C2 . . 110.93(13) ?
N2 C7 H7A . . 109.5 ?
C2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.0 ?
N1 C8 N2 . . 115.92(13) ?
N1 C8 C9 . . 121.27(14) ?
N2 C8 C9 . . 122.81(14) ?
C10 C9 C8 . . 118.62(15) ?
C10 C9 H9 . . 120.7 ?
C8 C9 H9 . . 120.7 ?
C9 C10 C11 . . 120.44(15) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 117.34(15) ?
C12 C11 H11 . . 121.3 ?
C10 C11 H11 . . 121.3 ?
N1 C12 C11 . . 124.42(15) ?
N1 C12 H12 . . 117.8 ?
C11 C12 H12 . . 117.8 ?
C12 N1 C8 . . 117.85(13) ?
C8 N2 C7 . . 122.91(13) ?
C8 N2 H2 . . 118.5 ?
C7 N2 H2 . . 118.5 ?
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
C1 C2 . 1.385(2) ?
C1 C6 . 1.386(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.395(2) ?
C2 C7 . 1.500(2) ?
C3 C4 . 1.378(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N2 . 1.448(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.3502(19) ?
C8 N2 . 1.3559(19) ?
C8 C9 . 1.409(2) ?
C9 C10 . 1.366(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.383(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.372(2) ?
C11 H11 . 0.9300 ?
C12 N1 . 1.3353(19) ?
C12 H12 . 0.9300 ?
N2 H2 . 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
N2 H2 N1 2_656 0.86 2.24 3.0518(19) 156.5
C12 H12 Cg1 2_656 0.93 2.72 3.536(2) 147
C4 H4 Cg2 2_666 0.93 3.14 3.804(2) 130
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21847
