#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226928.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_2226928
loop_
_publ_author_name
'Fairuz, Zainal A.'
'Aiyub, Zaharah'
'Abdullah, Zanariah'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N-(4-Chlorophenyl)-4-methylpyridin-2-amine
;
_journal_coeditor_code           HB5582
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2186
_journal_paper_doi               10.1107/S1600536810030138
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H11 Cl N2'
_chemical_formula_moiety         'C12 H11 Cl N2'
_chemical_formula_sum            'C12 H11 Cl N2'
_chemical_formula_weight         218.68
_chemical_name_systematic
;
N-(4-Chlorophenyl)-4-methylpyridin-2-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 98.7550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9335(15)
_cell_length_b                   4.0651(4)
_cell_length_c                   17.0153(16)
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.4
_cell_volume                     1089.26(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9785
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.1992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.120
_refine_ls_wR_factor_ref         0.132
_reflns_number_gt                1886
_reflns_number_total             2509
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5582.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226928
_cod_database_fobs_code          2226928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.59502(4) 1.02913(16) 0.10424(3) 0.0834(2) Uani d . 1 . .
N N1 0.60831(9) 0.5290(4) 0.56614(8) 0.0495(4) Uani d . 1 . .
N N2 0.57324(9) 0.6997(4) 0.43820(9) 0.0552(4) Uani d D 1 . .
H H2n 0.5222(7) 0.653(5) 0.4444(11) 0.061(6) Uiso d D 1 . .
C C1 0.63451(10) 0.6751(4) 0.50365(9) 0.0439(4) Uani d . 1 . .
C C2 0.66466(12) 0.5088(5) 0.63260(11) 0.0578(5) Uani d . 1 . .
H H2 0.6472 0.4101 0.6767 0.069 Uiso calc R 1 . .
C C3 0.74612(12) 0.6230(5) 0.64035(10) 0.0570(5) Uani d . 1 . .
H H3 0.7827 0.5985 0.6881 0.068 Uiso calc R 1 . .
C C4 0.77369(11) 0.7769(4) 0.57556(10) 0.0498(4) Uani d . 1 . .
C C5 0.71648(10) 0.8019(4) 0.50667(10) 0.0461(4) Uani d . 1 . .
H H5 0.7323 0.9030 0.4621 0.055 Uiso calc R 1 . .
C C6 0.86175(12) 0.9137(6) 0.58031(13) 0.0661(5) Uani d . 1 . .
H H6A 0.8620 1.0847 0.5414 0.099 Uiso calc R 1 . .
H H6B 0.8999 0.7416 0.5701 0.099 Uiso calc R 1 . .
H H6C 0.8797 1.0023 0.6325 0.099 Uiso calc R 1 . .
C C7 0.58319(10) 0.7850(4) 0.36041(9) 0.0428(4) Uani d . 1 . .
C C8 0.51945(11) 0.9664(4) 0.31600(11) 0.0496(4) Uani d . 1 . .
H H8 0.4740 1.0406 0.3396 0.059 Uiso calc R 1 . .
C C9 0.52239(12) 1.0389(4) 0.23723(11) 0.0544(4) Uani d . 1 . .
H H9 0.4789 1.1588 0.2077 0.065 Uiso calc R 1 . .
C C10 0.59014(12) 0.9323(4) 0.20290(10) 0.0493(4) Uani d . 1 . .
C C11 0.65418(11) 0.7545(4) 0.24569(10) 0.0481(4) Uani d . 1 . .
H H11 0.6998 0.6843 0.2219 0.058 Uiso calc R 1 . .
C C12 0.65108(10) 0.6791(4) 0.32428(10) 0.0462(4) Uani d . 1 . .
H H12 0.6946 0.5570 0.3532 0.055 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'
Cl Cl 0.1484 0.1585 '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 N1 C1 . . 116.69(15) ?
C1 N2 C7 . . 128.17(14) ?
C1 N2 H2n . . 117.2(13) ?
C7 N2 H2n . . 114.6(13) ?
N1 C1 N2 . . 114.12(15) ?
N1 C1 C5 . . 122.47(15) ?
N2 C1 C5 . . 123.36(15) ?
N1 C2 C3 . . 124.59(18) ?
N1 C2 H2 . . 117.7 ?
C3 C2 H2 . . 117.7 ?
C2 C3 C4 . . 119.00(16) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 117.32(16) ?
C5 C4 C6 . . 120.81(17) ?
C3 C4 C6 . . 121.87(16) ?
C4 C5 C1 . . 119.92(16) ?
C4 C5 H5 . . 120.0 ?
C1 C5 H5 . . 120.0 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C12 . . 118.64(15) ?
C8 C7 N2 . . 117.97(15) ?
C12 C7 N2 . . 123.27(15) ?
C9 C8 C7 . . 120.91(16) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C10 C9 C8 . . 119.40(16) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C11 C10 C9 . . 120.77(16) ?
C11 C10 Cl1 . . 119.67(14) ?
C9 C10 Cl1 . . 119.55(14) ?
C10 C11 C12 . . 119.99(16) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C7 . . 120.28(15) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
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
Cl1 C10 . 1.7376(18) ?
N1 C2 . 1.335(2) ?
N1 C1 . 1.339(2) ?
N2 C1 . 1.368(2) ?
N2 C7 . 1.400(2) ?
N2 H2n . 0.857(9) ?
C1 C5 . 1.398(2) ?
C2 C3 . 1.366(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.396(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(2) ?
C4 C6 . 1.500(3) ?
C5 H5 . 0.9300 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C8 . 1.383(2) ?
C7 C12 . 1.391(2) ?
C8 C9 . 1.380(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.373(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.367(2) ?
C11 C12 . 1.380(2) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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 H2n N1 3_666 0.857(9) 2.189(11) 3.029(2) 166.5(18)
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
C2 N1 C1 N2 . . . . -177.70(15) ?
C2 N1 C1 C5 . . . . 0.0(2) ?
C7 N2 C1 N1 . . . . -167.92(17) ?
C7 N2 C1 C5 . . . . 14.4(3) ?
C1 N1 C2 C3 . . . . -0.7(3) ?
N1 C2 C3 C4 . . . . 1.0(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C2 C3 C4 C6 . . . . 178.85(18) ?
C3 C4 C5 C1 . . . . -0.1(2) ?
C6 C4 C5 C1 . . . . -179.50(17) ?
N1 C1 C5 C4 . . . . 0.4(3) ?
N2 C1 C5 C4 . . . . 177.85(16) ?
C1 N2 C7 C8 . . . . -144.79(18) ?
C1 N2 C7 C12 . . . . 39.4(3) ?
C12 C7 C8 C9 . . . . 0.6(3) ?
N2 C7 C8 C9 . . . . -175.42(16) ?
C7 C8 C9 C10 . . . . -0.8(3) ?
C8 C9 C10 C11 . . . . 0.3(3) ?
C8 C9 C10 Cl1 . . . . -178.88(14) ?
C9 C10 C11 C12 . . . . 0.2(3) ?
Cl1 C10 C11 C12 . . . . 179.44(13) ?
C10 C11 C12 C7 . . . . -0.4(3) ?
C8 C7 C12 C11 . . . . -0.1(2) ?
N2 C7 C12 C11 . . . . 175.77(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745683
