#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/49/2234988.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_2234988
loop_
_publ_author_name
'Köppen, Robert'
'Emmerling, Franziska'
'Koch, Matthias'
_publ_section_title
;
 rac-1-(2-Aminocarbonyl-2-bromoethyl)pyridinium bromide
;
_journal_coeditor_code           FJ2549
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1666
_journal_paper_doi               10.1107/S1600536812019721
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H10 Br N2 O +, Br -'
_chemical_formula_moiety         'C8 H10 Br N2 O +, Br -'
_chemical_formula_sum            'C8 H10 Br2 N2 O'
_chemical_formula_weight         310.00
_chemical_name_systematic
;
rac-1-(2-Aminocarbonyl-2-bromoethyl)pyridinium bromide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 121.501(8)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   8.6024(9)
_cell_length_b                   16.1200(19)
_cell_length_c                   9.5092(12)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     1124.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996)'
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.1061
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10331
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    7.176
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.564
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0444
_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)+(0.0659P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                1442
_reflns_number_total             2252
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2549.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234988
_cod_database_fobs_code          2234988
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'
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
Br Br1 0.23648(10) 0.06295(5) 0.72065(9) 0.0538(3) Uani d . 1 1
O O1 0.3105(6) 0.2759(3) 0.8640(6) 0.0652(15) Uani d . 1 1
N N1 0.6197(6) 0.1137(3) 0.7616(6) 0.0384(12) Uani d . 1 1
N N2 0.0498(7) 0.2553(4) 0.6168(7) 0.0661(18) Uani d . 1 1
H H2A -0.0084 0.2935 0.6335 0.079 Uiso d R 1 1
H H2B -0.0038 0.2274 0.5263 0.079 Uiso d R 1 1
C C1 0.3180(8) 0.1706(4) 0.6882(7) 0.0357(14) Uani d . 1 1
H H1 0.2813 0.1761 0.5722 0.043 Uiso calc R 1 1
C C2 0.2227(9) 0.2392(4) 0.7308(8) 0.0460(16) Uani d . 1 1
C C3 0.5231(8) 0.1790(4) 0.7954(7) 0.0408(15) Uani d . 1 1
H H3A 0.5591 0.2329 0.7764 0.049 Uiso calc R 1 1
H H3B 0.5590 0.1762 0.9104 0.049 Uiso calc R 1 1
C C4 0.6778(10) 0.0453(4) 0.8562(8) 0.0487(17) Uani d . 1 1
H H4 0.6589 0.0398 0.9435 0.058 Uiso calc R 1 1
C C5 0.7646(11) -0.0161(5) 0.8247(9) 0.061(2) Uani d . 1 1
H H5 0.8030 -0.0639 0.8891 0.073 Uiso calc R 1 1
C C6 0.7945(10) -0.0071(5) 0.6982(10) 0.061(2) Uani d . 1 1
H H6 0.8561 -0.0482 0.6778 0.073 Uiso calc R 1 1
C C7 0.7336(10) 0.0633(4) 0.6000(9) 0.0541(18) Uani d . 1 1
H H7 0.7516 0.0698 0.5123 0.065 Uiso calc R 1 1
C C8 0.6458(8) 0.1229(4) 0.6362(8) 0.0432(15) Uani d . 1 1
H H8 0.6038 0.1707 0.5720 0.052 Uiso calc R 1 1
Br Br2 0.79943(9) 0.35088(4) 0.75292(7) 0.0465(3) Uani d . 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'
Br Br -0.2901 2.4595 '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
C8 N1 C4 120.9(5)
C8 N1 C3 119.4(5)
C4 N1 C3 119.7(5)
C2 N2 H2A 120.0
C2 N2 H2B 120.0
H2A N2 H2B 120.0
C3 C1 C2 110.5(5)
C3 C1 Br1 111.2(4)
C2 C1 Br1 108.0(4)
C3 C1 H1 109.1
C2 C1 H1 109.1
Br1 C1 H1 109.1
O1 C2 N2 124.5(6)
O1 C2 C1 119.0(6)
N2 C2 C1 116.4(5)
N1 C3 C1 112.3(5)
N1 C3 H3A 109.1
C1 C3 H3A 109.1
N1 C3 H3B 109.1
C1 C3 H3B 109.1
H3A C3 H3B 107.9
N1 C4 C5 120.3(6)
N1 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 119.5(7)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C7 120.2(7)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 117.9(6)
C8 C7 H7 121.1
C6 C7 H7 121.1
N1 C8 C7 121.2(6)
N1 C8 H8 119.4
C7 C8 H8 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.956(6)
O1 C2 1.235(7)
N1 C8 1.333(7)
N1 C4 1.343(8)
N1 C3 1.477(7)
N2 C2 1.330(8)
N2 H2A 0.8599
N2 H2B 0.8601
C1 C3 1.513(8)
C1 C2 1.550(9)
C1 H1 0.9800
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.364(9)
C4 H4 0.9300
C5 C6 1.363(10)
C5 H5 0.9300
C6 C7 1.386(10)
C6 H6 0.9300
C7 C8 1.373(9)
C7 H7 0.9300
C8 H8 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
N2 H2A Br2 1_455 0.86 2.62 3.406(7) 154
N2 H2B Br2 4_465 0.86 2.57 3.428(6) 173
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
C3 C1 C2 O1 -18.5(8)
Br1 C1 C2 O1 103.3(6)
C3 C1 C2 N2 160.2(6)
Br1 C1 C2 N2 -78.1(6)
C8 N1 C3 C1 83.1(7)
C4 N1 C3 C1 -96.1(7)
C2 C1 C3 N1 178.7(5)
Br1 C1 C3 N1 58.8(6)
C8 N1 C4 C5 -0.2(10)
C3 N1 C4 C5 178.9(6)
N1 C4 C5 C6 1.1(11)
C4 C5 C6 C7 -1.5(12)
C5 C6 C7 C8 1.0(11)
C4 N1 C8 C7 -0.3(9)
C3 N1 C8 C7 -179.4(6)
C6 C7 C8 N1 -0.1(10)
