#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/50/1505065.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_1505065
loop_
_publ_author_name
'Kolev, Tsonko'
'Koleva, Bojidarka B.'
'Spiteller, Michael'
'Mayer-Figge, Heike'
'Sheldrick, William S.'
_publ_section_title
;
 2-amino-4-nitroaniline, a known compound with unexpected properties.
;
_journal_issue                   40
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              10084
_journal_page_last               10089
_journal_paper_doi               10.1021/jp068761x
_journal_volume                  111
_journal_year                    2007
_chemical_formula_moiety         'C6 H7 N3 O2'
_chemical_formula_sum            'C6 H7 N3 O2'
_chemical_formula_weight         153.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   3.7590(8)
_cell_length_b                   10.307(2)
_cell_length_c                   17.290(4)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7.5
_cell_volume                     669.9(2)
_computing_cell_refinement       'Siemens R3m/V (Siemens, 1989)'
_computing_data_collection       'Siemens R3m/V (Siemens, 1989)'
_computing_data_reduction        'XDISK (Siemens, 1989)'
_computing_molecular_graphics    'Siemens SHELXTL-PLUS (Sheldrick, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens P4 4-circle-diffractometer'
_diffrn_measurement_method       'Profile fitted'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            738
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.118
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(4)
_refine_ls_extinction_coef       0.045(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0388
_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)+(0.0711P)²+0.1188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                640
_reflns_number_total             738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp068761xsi20061220_070651.cif
_cod_data_source_block           26-126
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constr.' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1505065
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3826(8) 0.4936(3) 0.00748(15) 0.0304(7) Uani 1 1 d .
N1 N 0.3478(7) 0.4579(2) -0.07275(13) 0.0375(7) Uani 1 1 d .
O1 O 0.2060(8) 0.3533(2) -0.08966(12) 0.0540(7) Uani 1 1 d .
O2 O 0.4580(8) 0.5343(2) -0.12320(12) 0.0580(8) Uani 1 1 d .
C2 C 0.2492(8) 0.4101(2) 0.06409(16) 0.0320(7) Uani 1 1 d .
H2 H 0.1490 0.3311 0.0499 0.038 Uiso 1 1 calc R
C3 C 0.2661(8) 0.4448(3) 0.14100(15) 0.0307(7) Uani 1 1 d .
N3 N 0.1392(7) 0.3604(2) 0.19991(14) 0.0404(7) Uani 1 1 d .
H31 H 0.0500 0.2863 0.1878 0.048 Uiso 1 1 calc R
H32 H 0.1516 0.3835 0.2476 0.048 Uiso 1 1 calc R
C4 C 0.4254(8) 0.5657(3) 0.16160(15) 0.0311(7) Uani 1 1 d .
N4 N 0.4485(9) 0.6021(3) 0.23746(14) 0.0506(9) Uani 1 1 d .
H21 H 0.5444 0.6751 0.2496 0.061 Uiso 1 1 calc R
H22 H 0.3672 0.5520 0.2731 0.061 Uiso 1 1 calc R
C5 C 0.5579(8) 0.6473(3) 0.10321(16) 0.0341(7) Uani 1 1 d .
H5 H 0.6595 0.7265 0.1165 0.041 Uiso 1 1 calc R
C6 C 0.5392(8) 0.6113(2) 0.02627(17) 0.0328(7) Uani 1 1 d .
H6 H 0.6299 0.6651 -0.0122 0.039 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0328(14) 0.0279(12) 0.0304(13) -0.0017(11) -0.0026(12) 0.0064(13)
N1 0.0467(16) 0.0336(13) 0.0322(12) 0.0015(11) -0.0023(12) 0.0035(13)
O1 0.0815(19) 0.0373(11) 0.0432(12) -0.0062(9) -0.0102(14) -0.0068(14)
O2 0.087(2) 0.0522(13) 0.0343(11) 0.0072(11) 0.0050(14) -0.0083(16)
C2 0.0351(15) 0.0249(12) 0.0360(14) 0.0001(12) -0.0022(15) 0.0004(14)
C3 0.0297(14) 0.0273(13) 0.0351(13) 0.0030(12) -0.0016(13) 0.0033(13)
N3 0.0509(16) 0.0365(12) 0.0336(12) 0.0069(11) -0.0002(13) -0.0066(14)
C4 0.0295(14) 0.0320(14) 0.0317(13) -0.0020(11) -0.0009(13) 0.0044(13)
N4 0.070(2) 0.0481(15) 0.0335(14) -0.0066(12) 0.0009(16) -0.0107(17)
C5 0.0342(15) 0.0287(13) 0.0393(15) -0.0020(12) -0.0006(14) -0.0006(14)
C6 0.0340(14) 0.0285(13) 0.0358(14) 0.0071(12) 0.0016(14) 0.0011(13)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 121.8(2)
C6 C1 N1 119.2(2)
C2 C1 N1 119.0(2)
O1 N1 O2 121.9(2)
O1 N1 C1 119.3(2)
O2 N1 C1 118.8(2)
C3 C2 C1 120.0(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 N3 121.1(2)
C2 C3 C4 119.1(2)
N3 C3 C4 119.7(2)
C3 N3 H31 120.0
C3 N3 H32 120.0
H31 N3 H32 120.0
N4 C4 C5 120.2(3)
N4 C4 C3 120.4(3)
C5 C4 C3 119.5(2)
C4 N4 H21 120.0
C4 N4 H22 120.0
H21 N4 H22 120.0
C6 C5 C4 120.8(3)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 118.8(3)
C5 C6 H6 120.6
C1 C6 H6 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.387(4)
C1 C2 1.397(4)
C1 N1 1.441(3)
N1 O1 1.238(3)
N1 O2 1.246(3)
C2 C3 1.379(4)
C2 H2 0.9300
C3 N3 1.422(4)
C3 C4 1.427(4)
N3 H31 0.8600
N3 H32 0.8600
C4 N4 1.367(4)
C4 C5 1.405(4)
N4 H21 0.8600
N4 H22 0.8600
C5 C6 1.383(4)
C5 H5 0.9300
C6 H6 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4286892
