#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/27/2232702.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_2232702
loop_
_publ_author_name
'Akhmad Aznan, Aina Mardia'
'Fairuz, Zainal Abidin'
'Abdullah, Zanariah'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N-(4-Chlorophenyl)-3-nitropyridin-2-amine
;
_journal_coeditor_code           HB6473
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3176
_journal_paper_doi               10.1107/S1600536811045570
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H8 Cl N3 O2'
_chemical_formula_moiety         'C11 H8 Cl N3 O2'
_chemical_formula_sum            'C11 H8 Cl N3 O2'
_chemical_formula_weight         249.65
_chemical_name_common            N-(4-Chlorphenyl)-3-nitropyridine-2-amine
_chemical_name_systematic
;
N-(4-Chlorophenyl)-3-nitropyridin-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
_cell_angle_alpha                90.00
_cell_angle_beta                 123.1530(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.472(3)
_cell_length_b                   3.8032(4)
_cell_length_c                   21.300(2)
_cell_measurement_reflns_used    2586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.973
_cell_measurement_theta_min      2.284
_cell_volume                     2066.6(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8919
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.8690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+1.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                1912
_reflns_number_total             2347
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6473.cif
_cod_data_source_block           I
_cod_original_cell_volume        2066.7(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2232702
_cod_database_fobs_code          2232702
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
_atom_site_symmetry_multiplicity
Cl Cl1 0.223442(15) 0.15167(11) 0.28841(2) 0.01760(13) Uani d . 1 1
O O1 0.00287(5) 1.1095(3) 0.32850(6) 0.0239(3) Uani d . 1 1
O O2 -0.01657(5) 1.3711(4) 0.40019(7) 0.0271(3) Uani d . 1 1
N N1 0.09477(5) 0.8069(4) 0.38672(8) 0.0151(3) Uani d . 1 1
H H1n 0.0640(8) 0.866(5) 0.3481(11) 0.021(5) Uiso d . 1 1
N N2 0.14771(5) 0.8205(4) 0.51652(7) 0.0155(3) Uani d . 1 1
N N3 0.01356(5) 1.1930(4) 0.39171(8) 0.0180(3) Uani d . 1 1
C C1 0.10203(6) 0.9037(4) 0.45291(9) 0.0141(3) Uani d . 1 1
C C2 0.06265(6) 1.0832(4) 0.45711(9) 0.0148(3) Uani d . 1 1
C C3 0.07133(7) 1.1672(4) 0.52649(9) 0.0175(3) Uani d . 1 1
H H3 0.0452 1.2859 0.5296 0.021 Uiso calc R 1 1
C C4 0.11814(7) 1.0768(4) 0.59046(9) 0.0181(4) Uani d . 1 1
H H4 0.1252 1.1299 0.6388 0.022 Uiso calc R 1 1
C C5 0.15475(6) 0.9047(4) 0.58188(9) 0.0172(3) Uani d . 1 1
H H5 0.1872 0.8427 0.6261 0.021 Uiso calc R 1 1
C C6 0.12870(6) 0.6443(4) 0.36965(9) 0.0137(3) Uani d . 1 1
C C7 0.18163(6) 0.5712(4) 0.42051(9) 0.0161(3) Uani d . 1 1
H H7 0.1978 0.6249 0.4722 0.019 Uiso calc R 1 1
C C8 0.21055(6) 0.4195(4) 0.39510(9) 0.0163(3) Uani d . 1 1
H H8 0.2467 0.3708 0.4294 0.020 Uiso calc R 1 1
C C9 0.18699(6) 0.3393(4) 0.32026(9) 0.0149(3) Uani d . 1 1
C C10 0.13421(6) 0.4065(4) 0.26931(9) 0.0161(3) Uani d . 1 1
H H10 0.1181 0.3478 0.2179 0.019 Uiso calc R 1 1
C C11 0.10550(6) 0.5593(4) 0.29426(9) 0.0158(3) Uani d . 1 1
H H11 0.0694 0.6076 0.2596 0.019 Uiso calc R 1 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'
O O 0.0106 0.0060 '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
C1 N1 C6 131.43(14)
C1 N1 H1n 113.1(12)
C6 N1 H1n 115.4(12)
C5 N2 C1 118.99(14)
O2 N3 O1 121.71(14)
O2 N3 C2 118.75(13)
O1 N3 C2 119.54(13)
N2 C1 N1 118.36(14)
N2 C1 C2 119.48(14)
N1 C1 C2 122.15(14)
C3 C2 C1 120.01(15)
C3 C2 N3 117.09(14)
C1 C2 N3 122.88(14)
C4 C3 C2 119.25(15)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 117.45(15)
C3 C4 H4 121.3
C5 C4 H4 121.3
N2 C5 C4 124.83(15)
N2 C5 H5 117.6
C4 C5 H5 117.6
C11 C6 C7 119.45(15)
C11 C6 N1 114.64(14)
C7 C6 N1 125.90(14)
C8 C7 C6 119.47(14)
C8 C7 H7 120.3
C6 C7 H7 120.3
C9 C8 C7 120.22(15)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 120.84(15)
C8 C9 Cl1 120.15(13)
C10 C9 Cl1 119.02(12)
C11 C10 C9 119.08(15)
C11 C10 H10 120.5
C9 C10 H10 120.5
C10 C11 C6 120.93(15)
C10 C11 H11 119.5
C6 C11 H11 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.7400(16)
O1 N3 1.2408(18)
O2 N3 1.2312(18)
N1 C1 1.353(2)
N1 C6 1.412(2)
N1 H1n 0.87(2)
N2 C5 1.327(2)
N2 C1 1.346(2)
N3 C2 1.440(2)
C1 C2 1.426(2)
C2 C3 1.389(2)
C3 C4 1.372(2)
C3 H3 0.9500
C4 C5 1.389(2)
C4 H4 0.9500
C5 H5 0.9500
C6 C11 1.393(2)
C6 C7 1.393(2)
C7 C8 1.387(2)
C7 H7 0.9500
C8 C9 1.378(2)
C8 H8 0.9500
C9 C10 1.386(2)
C10 C11 1.376(2)
C10 H10 0.9500
C11 H11 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
N1 H1n O1 . 0.87(2) 1.91(2) 2.6280(18) 138.2(17)
C7 H7 N2 . 0.95 2.31 2.909(2) 120
C3 H3 O2 5_586 0.95 2.48 3.340(3) 152
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
C5 N2 C1 N1 -178.05(15)
C5 N2 C1 C2 0.7(2)
C6 N1 C1 N2 -4.5(3)
C6 N1 C1 C2 176.74(16)
N2 C1 C2 C3 -0.7(2)
N1 C1 C2 C3 177.97(16)
N2 C1 C2 N3 177.63(14)
N1 C1 C2 N3 -3.7(3)
O2 N3 C2 C3 4.2(2)
O1 N3 C2 C3 -176.53(15)
O2 N3 C2 C1 -174.27(15)
O1 N3 C2 C1 5.0(2)
C1 C2 C3 C4 0.3(3)
N3 C2 C3 C4 -178.19(15)
C2 C3 C4 C5 0.2(3)
C1 N2 C5 C4 -0.2(3)
C3 C4 C5 N2 -0.2(3)
C1 N1 C6 C11 175.03(16)
C1 N1 C6 C7 -6.0(3)
C11 C6 C7 C8 0.9(2)
N1 C6 C7 C8 -178.01(15)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C10 -0.3(3)
C7 C8 C9 Cl1 179.57(13)
C8 C9 C10 C11 0.8(2)
Cl1 C9 C10 C11 -179.10(13)
C9 C10 C11 C6 -0.4(3)
C7 C6 C11 C10 -0.4(2)
N1 C6 C11 C10 178.60(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2353216
