#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/48/2234815.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_2234815
loop_
_publ_author_name
'He, Jian-Ling'
_publ_section_title
;
 2-Chloro-5-nitropyridin-4-amine
;
_journal_coeditor_code           SU2408
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1540
_journal_paper_doi               10.1107/S1600536812017643
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C5 H4 Cl N3 O2'
_chemical_formula_moiety         'C5 H4 Cl N3 O2'
_chemical_formula_sum            'C5 H4 Cl N3 O2'
_chemical_formula_weight         173.5
_chemical_name_systematic
;
2-Chloro-5-nitropyridin-4-amine
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.596(2)
_cell_length_b                   6.2782(10)
_cell_length_c                   7.3018(12)
_cell_measurement_reflns_used    2718
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      2.8
_cell_volume                     669.11(18)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo,1995)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3496
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  0.9267
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0282
_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)+(0.0499P)²+0.1012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                625
_reflns_number_total             663
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2408.cif
_cod_data_source_block           I
_cod_database_code               2234815
_cod_database_fobs_code          2234815
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,1/2-z
4 -x,1/2+y,-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,1/2+z
8 x,1/2-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_symmetry_multiplicity
Cl Cl1 0.49841(3) 0.2500 0.77100(7) 0.0475(2) Uani d S 1 2
O O1 0.10325(10) 0.2500 0.3741(2) 0.0610(5) Uani d S 1 2
O O2 0.18179(10) 0.2500 0.12421(19) 0.0495(4) Uani d S 1 2
N N1 0.32242(10) 0.2500 0.70422(19) 0.0329(4) Uani d S 1 2
N N2 0.36482(14) 0.2500 0.1360(2) 0.0492(5) Uani d S 1 2
H H2A 0.4186 0.2500 0.1145 0.059 Uiso d SR 1 2
H H2B 0.3196 0.2500 0.0623 0.059 Uiso d SR 1 2
N N3 0.17674(11) 0.2500 0.2932(2) 0.0377(4) Uani d S 1 2
C C1 0.40493(11) 0.2500 0.6229(2) 0.0317(4) Uani d S 1 2
C C2 0.42218(12) 0.2500 0.4395(2) 0.0350(4) Uani d S 1 2
H H2 0.4821 0.2500 0.3964 0.042 Uiso calc SR 1 2
C C3 0.34767(13) 0.2500 0.3155(3) 0.0329(4) Uani d S 1 2
C C4 0.26029(11) 0.2500 0.3989(2) 0.0311(4) Uani d S 1 2
C C5 0.25209(11) 0.2500 0.5895(2) 0.0330(4) Uani d S 1 2
H H5 0.1934 0.2500 0.6392 0.040 Uiso calc SR 1 2
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
Cl1 0.0280(3) 0.0797(4) 0.0347(4) 0.000 -0.00544(16) 0.000
O1 0.0275(8) 0.0978(12) 0.0575(10) 0.000 -0.0049(7) 0.000
O2 0.0551(9) 0.0551(8) 0.0384(8) 0.000 -0.0163(7) 0.000
N1 0.0277(8) 0.0446(8) 0.0264(8) 0.000 0.0025(5) 0.000
N2 0.0451(10) 0.0759(12) 0.0266(9) 0.000 0.0030(7) 0.000
N3 0.0346(9) 0.0395(8) 0.0390(10) 0.000 -0.0097(7) 0.000
C1 0.0261(8) 0.0403(9) 0.0288(8) 0.000 -0.0020(6) 0.000
C2 0.0262(8) 0.0479(10) 0.0310(9) 0.000 0.0059(7) 0.000
C3 0.0359(10) 0.0355(8) 0.0272(8) 0.000 0.0020(7) 0.000
C4 0.0296(9) 0.0327(8) 0.0311(9) 0.000 -0.0026(7) 0.000
C5 0.0258(9) 0.0397(9) 0.0333(10) 0.000 0.0046(6) 0.000
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C1 114.55(14)
C3 N2 H2A 112.1
C3 N2 H2B 118.4
H2A N2 H2B 129.5
O1 N3 O2 122.27(16)
O1 N3 C4 118.81(16)
O2 N3 C4 118.92(16)
N1 C1 C2 126.90(15)
N1 C1 Cl1 115.35(12)
C2 C1 Cl1 117.75(13)
C1 C2 C3 119.13(16)
C1 C2 H2 120.4
C3 C2 H2 120.4
N2 C3 C4 126.34(18)
N2 C3 C2 118.97(16)
C4 C3 C2 114.70(16)
C5 C4 C3 120.44(16)
C5 C4 N3 117.42(15)
C3 C4 N3 122.14(17)
N1 C5 C4 124.29(14)
N1 C5 H5 117.9
C4 C5 H5 117.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7410(16)
O1 N3 1.225(2)
O2 N3 1.236(2)
N1 C5 1.325(2)
N1 C1 1.343(2)
N2 C3 1.335(3)
N2 H2A 0.8009
N2 H2B 0.8515
N3 C4 1.443(2)
C1 C2 1.363(2)
C2 C3 1.415(3)
C2 H2 0.9300
C3 C4 1.413(2)
C4 C5 1.397(3)
C5 H5 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
_geom_hbond_publ_flag
N2 H2B O2 . 0.85 2.06 2.673(3) 128 yes
C5 H5 O1 . 0.93 2.34 2.682(2) 101 yes
N2 H2A Cl1 1_554 0.80 2.77 3.3023(18) 126 yes
N2 H2B N1 1_554 0.85 2.61 3.213(2) 128 yes
