#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/41/2014109.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_2014109
loop_
_publ_author_name
'Lozano, Virginia'
'Jones, Peter G.'
_publ_section_title
;
 Secondary interactions in the isomorphous compounds
 2,6-bis(chloromethyl)pyridinium chloride and
 2,6-bis(bromomethyl)pyridinium bromide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o653
_journal_page_last               o655
_journal_paper_doi               10.1107/S0108270104017007
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C7 H8 Br2 N + , Br -'
_chemical_formula_moiety         'C7 H8 Br2 N + , Br -'
_chemical_formula_sum            'C7 H8 Br3 N'
_chemical_formula_weight         345.87
_chemical_name_systematic
;
2,6-Bis(bromomethyl)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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.146(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4633(6)
_cell_length_b                   15.0136(12)
_cell_length_c                   8.7377(6)
_cell_measurement_reflns_used    4337
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.7
_cell_volume                     966.62(13)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17828
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    12.458
_exptl_absorpt_correction_T_max  0.608
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.683
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0220
_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)+(0.0299P)²+0.6042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0573
_reflns_number_gt                2503
_reflns_number_total             2825
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1577.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014109
_cod_database_fobs_code          2014109
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N 0.5718(2) 0.24097(11) 0.1566(2) 0.0133(3) Uani d . 1 . . N
H1 0.497(4) 0.1995(17) 0.115(3) 0.018(6) Uiso d . 1 . . H
C2 0.7484(3) 0.22112(13) 0.2048(2) 0.0144(4) Uani d . 1 . . C
C3 0.8637(3) 0.28755(14) 0.2715(2) 0.0164(4) Uani d . 1 . . C
H3 0.9889 0.2755 0.3039 0.020 Uiso calc R 1 . . H
C4 0.7947(3) 0.37227(14) 0.2907(3) 0.0181(4) Uani d . 1 . . C
H4 0.8728 0.4182 0.3369 0.022 Uiso calc R 1 . . H
C5 0.6115(3) 0.38974(14) 0.2424(3) 0.0170(4) Uani d . 1 . . C
H5 0.5634 0.4472 0.2567 0.020 Uiso calc R 1 . . H
C6 0.4995(3) 0.32244(13) 0.1730(2) 0.0135(4) Uani d . 1 . . C
C7 0.8049(3) 0.12665(13) 0.1883(3) 0.0170(4) Uani d . 1 . . C
H7A 0.9283 0.1243 0.1605 0.020 Uiso calc R 1 . . H
H7B 0.7200 0.0966 0.1058 0.020 Uiso calc R 1 . . H
C8 0.3043(3) 0.33418(14) 0.1097(2) 0.0154(4) Uani d . 1 . . C
H8A 0.2508 0.3814 0.1675 0.019 Uiso calc R 1 . . H
H8B 0.2374 0.2780 0.1192 0.019 Uiso calc R 1 . . H
Br1 0.80166(3) 0.067970(15) 0.38717(3) 0.02218(7) Uani d . 1 . . Br
Br2 0.28757(3) 0.367763(14) -0.10939(2) 0.01665(6) Uani d . 1 . . Br
Br3 0.27054(3) 0.096247(13) 0.00963(2) 0.01639(6) Uani d . 1 . . Br
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
N 0.0145(8) 0.0118(7) 0.0135(8) -0.0012(6) 0.0012(6) -0.0008(6)
C2 0.0142(9) 0.0160(9) 0.0129(10) 0.0013(7) 0.0019(7) 0.0010(7)
C3 0.0139(9) 0.0197(9) 0.0151(10) -0.0010(8) 0.0006(7) 0.0013(7)
C4 0.0208(11) 0.0163(9) 0.0161(10) -0.0044(8) 0.0001(8) -0.0015(7)
C5 0.0212(11) 0.0138(9) 0.0159(10) -0.0001(8) 0.0024(8) -0.0013(7)
C6 0.0151(9) 0.0155(9) 0.0102(9) 0.0009(7) 0.0031(7) 0.0008(6)
C7 0.0177(10) 0.0156(9) 0.0169(11) 0.0015(8) 0.0004(8) 0.0004(7)
C8 0.0152(10) 0.0176(9) 0.0136(10) 0.0022(7) 0.0030(7) 0.0007(7)
Br1 0.02415(13) 0.01936(11) 0.02259(13) -0.00011(8) 0.00233(9) 0.00582(8)
Br2 0.01485(11) 0.01887(11) 0.01567(11) 0.00107(7) 0.00069(8) 0.00073(7)
Br3 0.01741(11) 0.01539(10) 0.01555(11) -0.00171(7) 0.00009(7) -0.00152(7)
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'
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
_geom_angle_publ_flag
C2 N C6 123.49(18) y
C2 N H1 120.0(17) ?
C6 N H1 116.5(17) ?
N C2 C3 118.85(19) ?
N C2 C7 117.10(18) ?
C3 C2 C7 123.99(19) ?
C2 C3 C4 119.5(2) ?
C2 C3 H3 120.3 ?
C4 C3 H3 120.3 ?
C5 C4 C3 120.03(19) ?
C5 C4 H4 120.0 ?
C3 C4 H4 120.0 ?
C6 C5 C4 119.36(19) ?
C6 C5 H5 120.3 ?
C4 C5 H5 120.3 ?
N C6 C5 118.77(19) ?
N C6 C8 116.88(18) ?
C5 C6 C8 124.31(18) ?
C2 C7 Br1 107.43(15) ?
C2 C7 H7A 110.2 ?
Br1 C7 H7A 110.2 ?
C2 C7 H7B 110.2 ?
Br1 C7 H7B 110.2 ?
H7A C7 H7B 108.5 ?
C6 C8 Br2 107.47(14) ?
C6 C8 H8A 110.2 ?
Br2 C8 H8A 110.2 ?
C6 C8 H8B 110.2 ?
Br2 C8 H8B 110.2 ?
H8A C8 H8B 108.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N C2 . 1.351(3) ?
N C6 . 1.354(3) ?
N H1 . 0.88(3) ?
C2 C3 . 1.384(3) ?
C2 C7 . 1.493(3) ?
C3 C4 . 1.392(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.390(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9500 ?
C6 C8 . 1.484(3) ?
C7 Br1 . 1.952(2) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 Br2 . 1.964(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
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
N H1 Br3 . 0.88(3) 2.37(3) 3.2417(17) 174(2)
C7 H7A Br3 1_655 0.99 3.08 4.056(2) 167
C7 H7B Br3 3_655 0.99 3.07 3.768(2) 129
C8 H8A Br3 4_566 0.99 2.99 3.694(2) 129
C8 H8B Br3 . 0.99 2.92 3.677(2) 134
C3 H3 Br2 4_666 0.95 3.10 3.935(2) 147
C7 H7A Br2 4_666 0.99 3.09 3.753(2) 126
C8 H8A Br1 2_655 0.99 2.86 3.599(2) 132
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
_geom_torsion_publ_flag
C6 N C2 C3 -1.5(3) ?
C6 N C2 C7 175.88(19) ?
N C2 C3 C4 1.5(3) ?
C7 C2 C3 C4 -175.7(2) ?
C2 C3 C4 C5 -0.3(3) ?
C3 C4 C5 C6 -1.0(3) ?
C2 N C6 C5 0.3(3) ?
C2 N C6 C8 178.21(18) ?
C4 C5 C6 N 1.0(3) ?
C4 C5 C6 C8 -176.8(2) ?
N C2 C7 Br1 -96.15(19) y
C3 C2 C7 Br1 81.1(2) y
N C6 C8 Br2 -87.12(19) y
C5 C6 C8 Br2 90.7(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14007283
