#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/83/2208301.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_2208301
loop_
_publ_author_name
'Sundar, T. V.'
'Parthasarathi, V.'
'Ravikumar, K.'
'Venkatesan, P.'
'Nallu, M.'
_publ_section_title
;
 4-Amino-1-(4-nitrobenzyl)pyridinium bromide
;
_journal_coeditor_code           CV6638
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1118
_journal_page_last               o1120
_journal_paper_doi               10.1107/S1600536806005605
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H12 N3 O2 +, Br -'
_chemical_formula_moiety         'C12 H12 N3 O2 +, Br -'
_chemical_formula_sum            'C12 H12 Br N3 O2'
_chemical_formula_weight         310.16
_chemical_melting_point          562.0(10)
_chemical_name_systematic
;
4-Amino-1-(4-nitrobenzyl)pyridinium bromide
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c 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            8
_cell_length_a                   6.7257(4)
_cell_length_b                   14.3806(8)
_cell_length_c                   26.0364(15)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      53.138
_cell_measurement_theta_min      5.391
_cell_volume                     2518.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003)
and Qmol (Gans & Shalloway, 2001)
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF99 (Beurskens et al.,  1999)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11396
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.262
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.383
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1205
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.033P)²+2.5916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0677
_reflns_number_gt                1134
_reflns_number_total             1205
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6638.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:

'_chemical_melting_point' value '561--563' was changed to '562.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '561--563' was changed to '562.0(10)'
- the average value was taken and precision was
estimated.

'_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_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_formula_sum        'C12 H12 Br1 N3 O2'
_cod_database_code               2208301
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x, -y, -z'
'-x, y+1/2, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, 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
Br Br 0.0000 0.63077(2) 0.397489(12) 0.05028(15) Uani d S 1
O O1 0.0000 0.20910(16) 0.31724(9) 0.0799(9) Uani d S 1
O O2 0.0000 0.33546(18) 0.35970(7) 0.0620(6) Uani d S 1
N N1 0.0000 0.45006(15) 0.08501(8) 0.0356(5) Uani d S 1
N N2 0.0000 0.3128(2) -0.05308(10) 0.0560(7) Uani d SD 1
H H2N -0.117(3) 0.3041(18) -0.0675(9) 0.069(8) Uiso d D 1
N N3 0.0000 0.29295(18) 0.31927(9) 0.0448(6) Uani d S 1
C C1 0.1729(3) 0.42638(14) 0.06279(7) 0.0426(4) Uani d . 1
H H1 0.2918 0.4424 0.0787 0.051 Uiso calc R 1
C C2 0.1777(3) 0.37939(13) 0.01747(8) 0.0446(5) Uani d . 1
H H2 0.2990 0.3630 0.0029 0.053 Uiso calc R 1
C C3 0.0000 0.35571(18) -0.00732(10) 0.0403(6) Uani d S 1
C C6 0.0000 0.50430(19) 0.13327(10) 0.0415(6) Uani d SD 1
H H6 0.115(3) 0.5424(13) 0.1325(7) 0.042(5) Uiso d D 1
C C7 0.0000 0.44449(18) 0.18069(9) 0.0329(5) Uani d S 1
C C8 0.0000 0.49016(19) 0.22810(9) 0.0387(6) Uani d S 1
H H8 0.0000 0.5548 0.2289 0.046 Uiso calc SR 1
C C9 0.0000 0.44144(19) 0.27341(10) 0.0381(6) Uani d S 1
H H9 0.0000 0.4722 0.3048 0.046 Uiso calc SR 1
C C10 0.0000 0.34555(19) 0.27113(9) 0.0350(6) Uani d S 1
C C11 0.0000 0.29802(19) 0.22501(10) 0.0379(6) Uani d S 1
H H11 0.0000 0.2334 0.2244 0.045 Uiso calc SR 1
C C12 0.0000 0.34850(19) 0.17977(10) 0.0353(6) Uani d S 1
H H12 0.0000 0.3175 0.1484 0.042 Uiso calc SR 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
Br 0.0510(2) 0.0486(2) 0.0513(2) 0.000 0.000 0.01078(12)
O1 0.146(3) 0.0410(14) 0.0524(13) 0.000 0.000 0.0156(10)
O2 0.0914(18) 0.0677(15) 0.0268(10) 0.000 0.000 0.0049(10)
N1 0.0461(13) 0.0361(12) 0.0246(10) 0.000 0.000 0.0039(8)
N2 0.084(2) 0.0501(15) 0.0341(13) 0.000 0.000 -0.0068(11)
N3 0.0491(14) 0.0510(15) 0.0344(12) 0.000 0.000 0.0102(10)
C1 0.0403(11) 0.0507(11) 0.0367(9) -0.0015(9) -0.0031(8) 0.0031(8)
C2 0.0442(12) 0.0517(12) 0.0379(10) 0.0063(8) 0.0064(9) 0.0003(8)
C3 0.0628(18) 0.0303(13) 0.0276(13) 0.000 0.000 0.0048(10)
C6 0.0631(19) 0.0338(14) 0.0276(12) 0.000 0.000 0.0003(10)
C7 0.0348(13) 0.0363(14) 0.0276(12) 0.000 0.000 0.0022(10)
C8 0.0511(16) 0.0320(13) 0.0331(12) 0.000 0.000 -0.0020(10)
C9 0.0465(15) 0.0409(15) 0.0270(12) 0.000 0.000 -0.0043(10)
C10 0.0368(14) 0.0395(14) 0.0287(12) 0.000 0.000 0.0061(10)
C11 0.0440(15) 0.0320(13) 0.0377(13) 0.000 0.000 0.0024(11)
C12 0.0412(14) 0.0368(13) 0.0278(12) 0.000 0.000 -0.0031(10)
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'
Br Br -0.2901 2.4595 '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
C1 N1 C1 . 11 120.0(2)
C1 N1 C6 . . 119.98(11)
C1 N1 C6 11 . 119.98(11)
C3 N2 H2N . . 116.3(18)
O1 N3 O2 . . 122.7(2)
O1 N3 C10 . . 118.6(2)
O2 N3 C10 . . 118.7(2)
N1 C1 C2 . . 121.33(19)
N1 C1 H1 . . 119.3
C2 C1 H1 . . 119.3
C1 C2 C3 . . 120.1(2)
C1 C2 H2 . . 120.0
C3 C2 H2 . . 120.0
N2 C3 C2 . . 121.42(12)
N2 C3 C2 . 11 121.42(12)
C2 C3 C2 . 11 117.2(2)
N1 C6 C7 . . 113.3(2)
N1 C6 H6 . . 106.7(12)
C7 C6 H6 . . 110.3(12)
C12 C7 C8 . . 119.0(2)
C12 C7 C6 . . 123.9(2)
C8 C7 C6 . . 117.1(2)
C9 C8 C7 . . 121.3(2)
C9 C8 H8 . . 119.4
C7 C8 H8 . . 119.4
C8 C9 C10 . . 118.2(2)
C8 C9 H9 . . 120.9
C10 C9 H9 . . 120.9
C9 C10 C11 . . 122.1(2)
C9 C10 N3 . . 118.6(2)
C11 C10 N3 . . 119.2(2)
C10 C11 C12 . . 118.7(2)
C10 C11 H11 . . 120.7
C12 C11 H11 . . 120.7
C7 C12 C11 . . 120.7(2)
C7 C12 H12 . . 119.7
C11 C12 H12 . . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 N3 . 1.207(3)
O2 N3 . 1.217(3)
N1 C1 . 1.343(2)
N1 C1 11 1.343(2)
N1 C6 . 1.479(3)
N2 C3 . 1.342(4)
N2 H2N . 0.881(16)
N3 C10 . 1.464(3)
C1 C2 . 1.360(3)
C1 H1 . 0.9300
C2 C3 . 1.400(3)
C2 H2 . 0.9300
C3 C2 11 1.400(3)
C6 C7 . 1.505(3)
C6 H6 . 0.948(15)
C7 C12 . 1.381(4)
C7 C8 . 1.398(3)
C8 C9 . 1.372(3)
C8 H8 . 0.9300
C9 C10 . 1.380(4)
C9 H9 . 0.9300
C10 C11 . 1.382(4)
C11 C12 . 1.384(4)
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
_geom_hbond_publ_flag
N2 H2N Br 16_465 0.881(16) 2.888(19) 3.6912(11) 152(2) yes
C8 H8 O1 10_566 0.93 2.52 3.363(4) 150 yes
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_4
_geom_torsion
C1 N1 C1 C2 11 . 0.8(4)
C6 N1 C1 C2 . . -177.6(2)
N1 C1 C2 C3 . . 0.8(3)
C1 C2 C3 N2 . . 177.2(2)
C1 C2 C3 C2 . 11 -2.3(4)
C1 N1 C6 C7 . . -90.78(19)
C1 N1 C6 C7 11 . 90.78(19)
N1 C6 C7 C12 . . 0.0
N1 C6 C7 C8 . . 180.0
C12 C7 C8 C9 . . 0.0
C6 C7 C8 C9 . . 180.0
C7 C8 C9 C10 . . 0.0
C8 C9 C10 C11 . . 0.0
C8 C9 C10 N3 . . 180.0
O1 N3 C10 C9 . . 180.0
O2 N3 C10 C9 . . 0.0
O1 N3 C10 C11 . . 0.0
O2 N3 C10 C11 . . 180.0
C9 C10 C11 C12 . . 0.0
N3 C10 C11 C12 . . 180.0
C8 C7 C12 C11 . . 0.0
C6 C7 C12 C11 . . 180.0
C10 C11 C12 C7 . . 0.0
