#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/85/2208525.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_2208525
loop_
_publ_author_name
'Lemmerer, Andreas'
'Billing, David G.'
_publ_section_title
;
 p-Nitroaniline hydrobromide
;
_journal_coeditor_code           BT2035
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1562
_journal_page_last               o1564
_journal_paper_doi               10.1107/S1600536806010166
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C6 H7 N2 O2 + , Br -'
_chemical_formula_moiety         'C6 H7 N2 O2 + , Br -'
_chemical_formula_sum            'C6 H7 Br N2 O2'
_chemical_formula_weight         219.05
_chemical_name_systematic
;
p-Nitroaniline hydrobromide
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   20.625(5)
_cell_length_b                   30.408(5)
_cell_length_c                   5.080(5)
_cell_measurement_reflns_used    898
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.867
_cell_measurement_theta_min      3.3295
_cell_volume                     3186(3)
_computing_cell_refinement       SMART-NT
_computing_data_collection       'SMART-NT (Bruker (1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4378
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    5.111
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.291
_refine_ls_abs_structure_details 'Flack (1983), 425 Friedel pairs'
_refine_ls_abs_structure_Flack   0.022(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1254
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+2.6422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                1157
_reflns_number_total             1254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2035.cif
_cod_data_source_block           I
_cod_depositor_comments
;
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_enum 1527 2010-12-29 10:47:43Z 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 
;
_cod_database_code               2208525
_cod_database_fobs_code          2208525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
C C1 0.39716(15) 0.25556(12) 0.1947(8) 0.0316(9) Uani d . 1
C C2 0.35624(17) 0.25214(11) 0.4062(9) 0.0370(9) Uani d . 1
H H2 0.3539 0.2262 0.5029 0.044 Uiso calc R 1
C C3 0.31829(17) 0.28829(13) 0.4732(8) 0.0377(9) Uani d . 1
H H3 0.289 0.2868 0.612 0.045 Uiso calc R 1
C C4 0.32510(15) 0.32612(12) 0.3302(8) 0.0281(9) Uani d . 1
C C5 0.36652(15) 0.32939(11) 0.1168(9) 0.0339(7) Uani d . 1
H H5 0.3694 0.3554 0.0217 0.041 Uiso calc R 1
C C6 0.40326(17) 0.29348(13) 0.0476(7) 0.0347(9) Uani d . 1
H H6 0.4315 0.2947 -0.0948 0.042 Uiso calc R 1
N N1 0.43751(14) 0.21729(10) 0.1249(13) 0.0413(7) Uani d . 1
N N2 0.28665(15) 0.36505(10) 0.3998(9) 0.0397(7) Uani d . 1
H H2A 0.2618 0.3589 0.5383 0.06 Uiso calc R 1
H H2B 0.2617 0.3726 0.2641 0.06 Uiso calc R 1
H H2C 0.3131 0.3872 0.4392 0.06 Uiso calc R 1
O O1 0.44171(14) 0.18736(10) 0.2833(7) 0.0549(9) Uani d . 1
O O2 0.46439(14) 0.21709(10) -0.0926(8) 0.0588(9) Uani d . 1
Br Br1 0.186979(17) 0.344520(12) 0.88052(13) 0.03852(13) Uani d . 1
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
C1 0.0266(17) 0.0278(19) 0.040(2) -0.0006(14) -0.0060(16) -0.0015(16)
C2 0.0400(18) 0.0279(18) 0.043(2) -0.0033(14) 0.004(2) 0.0094(19)
C3 0.039(2) 0.037(2) 0.037(2) -0.0055(17) 0.0123(18) 0.0057(17)
C4 0.0257(16) 0.0292(18) 0.029(3) -0.0031(13) -0.0006(16) 0.0005(16)
C5 0.0369(17) 0.0313(18) 0.0337(19) -0.0032(15) 0.004(2) 0.0081(18)
C6 0.0295(17) 0.042(2) 0.033(2) -0.0031(16) 0.0040(16) 0.0035(17)
N1 0.0312(14) 0.0361(17) 0.056(2) 0.0027(14) 0.0010(18) 0.004(3)
N2 0.0449(16) 0.0351(17) 0.0391(19) 0.0017(13) 0.0080(19) 0.0010(18)
O1 0.0561(18) 0.0418(19) 0.067(2) 0.0137(14) -0.0062(15) 0.0100(17)
O2 0.0550(17) 0.0518(19) 0.070(2) 0.0078(14) 0.026(2) -0.002(2)
Br1 0.03616(18) 0.0443(2) 0.03514(19) -0.00076(15) 0.00584(18) -0.00469(18)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 '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
C2 C1 C6 123.0(3)
C2 C1 N1 118.5(4)
C6 C1 N1 118.6(4)
C1 C2 C3 118.6(3)
C1 C2 H2 120.7
C3 C2 H2 120.7
C4 C3 C2 118.5(4)
C4 C3 H3 120.8
C2 C3 H3 120.8
C3 C4 C5 122.7(3)
C3 C4 N2 119.6(3)
C5 C4 N2 117.7(4)
C6 C5 C4 118.9(3)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 118.4(3)
C5 C6 H6 120.8
C1 C6 H6 120.8
O1 N1 O2 123.7(4)
O1 N1 C1 118.1(5)
O2 N1 C1 118.2(4)
C4 N2 H2A 109.5
C4 N2 H2B 109.5
H2A N2 H2B 109.5
C4 N2 H2C 109.5
H2A N2 H2C 109.5
H2B N2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.370(5) ?
C1 C6 1.380(5) ?
C1 N1 1.474(5) y
C2 C3 1.392(5) ?
C2 H2 0.93 ?
C3 C4 1.368(6) ?
C3 H3 0.93 ?
C4 C5 1.384(5) ?
C4 N2 1.468(5) y
C5 C6 1.375(5) ?
C5 H5 0.93 ?
C6 H6 0.93 ?
N1 O1 1.218(6) y
N1 O2 1.236(7) y
N2 H2A 0.89 ?
N2 H2B 0.89 ?
N2 H2C 0.89 ?
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 H2A Br1 . 0.89 2.37 3.253(4) 174.4
N2 H2B O1 11_554 0.89 2.48 2.915(5) 110.3
N2 H2B Br1 1_554 0.89 2.63 3.402(5) 146.1
N2 H2C Br1 8_554 0.89 2.79 3.535(4) 142.3
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
C6 C1 C2 C3 1.1(6)
N1 C1 C2 C3 179.7(4)
C1 C2 C3 C4 -2.1(6)
C2 C3 C4 C5 2.2(6)
C2 C3 C4 N2 -178.8(4)
C3 C4 C5 C6 -1.1(6)
N2 C4 C5 C6 179.8(4)
C4 C5 C6 C1 0.0(5)
C2 C1 C6 C5 -0.1(5)
N1 C1 C6 C5 -178.7(4)
C2 C1 N1 O1 -13.0(5)
C6 C1 N1 O1 165.6(3)
C2 C1 N1 O2 165.9(4)
C6 C1 N1 O2 -15.4(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13757042
