#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/44/2014441.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_2014441
loop_
_publ_author_name
'Jones, Peter G.'
'Lozano, Virginia'
_publ_section_title
;
 Secondary interactions in 3-bromopyridinium tribromoacetate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o876
_journal_page_last               o878
_journal_paper_doi               10.1107/S0108270104024977
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C5 H5 Br N + , C2 Br3 O2 -'
_chemical_formula_moiety         'C5 H5 Br N + , C2 Br3 O2 -'
_chemical_formula_sum            'C7 H5 Br4 N O2'
_chemical_formula_weight         454.76
_chemical_name_systematic
;
3-bromopyridinium tribromoacetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                96.520(4)
_cell_angle_beta                 95.900(4)
_cell_angle_gamma                103.883(4)
_cell_formula_units_Z            4
_cell_length_a                   6.2478(4)
_cell_length_b                   12.6754(8)
_cell_length_c                   15.4525(8)
_cell_measurement_reflns_used    7447
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.3
_cell_volume                     1169.53(12)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.041
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22507
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.34
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.738
_exptl_absorpt_correction_T_max  0.382
_exptl_absorpt_correction_T_min  0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.92
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         6811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0219P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0537
_refine_ls_wR_factor_ref         0.0560
_reflns_number_gt                5031
_reflns_number_total             6811
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1583.cif
_cod_data_source_block           I
_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_database_code               2014441
_cod_database_fobs_code          2014441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 0.2666(5) 0.3606(2) 0.01628(18) 0.0195(6) Uani d . 1 . . N
H01 0.192(6) 0.385(3) 0.043(3) 0.036(12) Uiso d . 1 . . H
C2 0.3737(5) 0.2933(3) 0.0520(2) 0.0206(7) Uani d . 1 . . C
H2 0.3457 0.2725 0.1077 0.025 Uiso calc R 1 . . H
C3 0.5245(5) 0.2545(3) 0.0073(2) 0.0206(7) Uani d . 1 . . C
C4 0.5639(5) 0.2848(3) -0.0737(2) 0.0222(7) Uani d . 1 . . C
H4 0.6707 0.2597 -0.1044 0.027 Uiso calc R 1 . . H
C5 0.4455(5) 0.3524(3) -0.1098(2) 0.0249(7) Uani d . 1 . . C
H5 0.4669 0.3725 -0.1662 0.030 Uiso calc R 1 . . H
C6 0.2956(5) 0.3903(3) -0.0625(2) 0.0228(7) Uani d . 1 . . C
H6 0.2141 0.4372 -0.0862 0.027 Uiso calc R 1 . . H
Br1 0.67862(7) 0.16420(4) 0.06202(2) 0.03651(10) Uani d . 1 . . Br
N11 0.3039(5) 0.8782(2) 0.48251(18) 0.0201(6) Uani d . 1 . . N
H011 0.245(6) 0.914(3) 0.453(3) 0.042(13) Uiso d . 1 . . H
C12 0.4472(5) 0.8286(3) 0.4468(2) 0.0197(7) Uani d . 1 . . C
H12 0.4845 0.8404 0.3899 0.024 Uiso calc R 1 . . H
C13 0.5396(5) 0.7606(3) 0.4933(2) 0.0187(7) Uani d . 1 . . C
C14 0.4851(5) 0.7427(3) 0.5762(2) 0.0233(7) Uani d . 1 . . C
H14 0.5469 0.6949 0.6082 0.028 Uiso calc R 1 . . H
C15 0.3367(5) 0.7972(3) 0.6111(2) 0.0243(7) Uani d . 1 . . C
H15 0.2986 0.7881 0.6682 0.029 Uiso calc R 1 . . H
C16 0.2454(5) 0.8643(3) 0.5622(2) 0.0226(7) Uani d . 1 . . C
H16 0.1419 0.9003 0.5850 0.027 Uiso calc R 1 . . H
Br11 0.73370(6) 0.68930(3) 0.43950(2) 0.03000(9) Uani d . 1 . . Br
C7 0.0055(5) 0.4965(3) 0.27340(19) 0.0170(6) Uani d . 1 . . C
C8 0.0984(5) 0.4347(3) 0.1980(2) 0.0175(6) Uani d . 1 . . C
Br2 0.11141(6) 0.46883(3) 0.38836(2) 0.02665(8) Uani d . 1 . . Br
Br3 -0.31699(5) 0.44636(3) 0.25431(2) 0.01900(7) Uani d . 1 . . Br
Br4 0.09679(5) 0.65316(3) 0.26887(2) 0.02019(7) Uani d . 1 . . Br
O1 0.0379(4) 0.45329(19) 0.12177(14) 0.0241(5) Uani d . 1 . . O
O2 0.2172(3) 0.37511(19) 0.21896(14) 0.0224(5) Uani d . 1 . . O
C17 -0.0025(5) 0.9897(3) 0.2265(2) 0.0184(7) Uani d . 1 . . C
C18 0.1295(5) 0.9479(3) 0.3003(2) 0.0192(7) Uani d . 1 . . C
Br12 0.04550(6) 0.93276(3) 0.11044(2) 0.02841(9) Uani d . 1 . . Br
Br13 0.09443(5) 1.14903(3) 0.23974(2) 0.02129(8) Uani d . 1 . . Br
Br14 -0.31807(5) 0.94628(3) 0.23634(2) 0.02114(8) Uani d . 1 . . Br
O11 0.1076(4) 0.9856(2) 0.37772(14) 0.0270(6) Uani d . 1 . . O
O12 0.2401(3) 0.88441(18) 0.27873(14) 0.0228(5) Uani d . 1 . . O
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
_geom_angle_publ_flag
C6 N1 C2 122.8(3) y
N1 C2 C3 119.4(3) ?
C2 C3 C4 120.1(3) ?
C2 C3 Br1 117.8(2) ?
C4 C3 Br1 122.1(2) ?
C3 C4 C5 119.0(3) ?
C6 C5 C4 119.3(3) ?
N1 C6 C5 119.5(3) ?
C16 N11 C12 122.8(3) y
N11 C12 C13 119.2(3) ?
C12 C13 C14 120.7(3) ?
C12 C13 Br11 117.9(2) ?
C14 C13 Br11 121.4(2) ?
C13 C14 C15 118.0(3) ?
C16 C15 C14 119.8(3) ?
N11 C16 C15 119.5(3) ?
C8 C7 Br2 112.4(2) ?
C8 C7 Br4 108.9(2) ?
Br2 C7 Br4 108.89(15) ?
C8 C7 Br3 108.22(19) ?
Br2 C7 Br3 108.63(14) ?
Br4 C7 Br3 109.83(14) ?
O2 C8 O1 128.1(3) ?
O2 C8 C7 117.6(3) ?
O1 C8 C7 114.3(3) ?
C18 C17 Br12 112.1(2) ?
C18 C17 Br14 109.5(2) ?
Br12 C17 Br14 109.16(15) ?
C18 C17 Br13 109.3(2) ?
Br12 C17 Br13 107.78(15) ?
Br14 C17 Br13 109.01(14) ?
O12 C18 O11 127.5(3) ?
O12 C18 C17 118.2(3) ?
O11 C18 C17 114.3(3) ?
C6 N1 H01 119(3) ?
C2 N1 H01 119(3) ?
N1 C2 H2 120.3 ?
C3 C2 H2 120.3 ?
C3 C4 H4 120.5 ?
C5 C4 H4 120.5 ?
C6 C5 H5 120.4 ?
C4 C5 H5 120.4 ?
N1 C6 H6 120.2 ?
C5 C6 H6 120.2 ?
C16 N11 H011 120(3) ?
C12 N11 H011 117(3) ?
N11 C12 H12 120.4 ?
C13 C12 H12 120.4 ?
C13 C14 H14 121.0 ?
C15 C14 H14 121.0 ?
C16 C15 H15 120.1 ?
C14 C15 H15 120.1 ?
N11 C16 H16 120.2 ?
C15 C16 H16 120.2 ?
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
N1 C6 . 1.332(4) ?
N1 C2 . 1.336(4) ?
C2 C3 . 1.373(4) ?
C3 C4 . 1.380(4) ?
C3 Br1 . 1.880(3) ?
C4 C5 . 1.385(5) ?
C5 C6 . 1.385(4) ?
N11 C16 . 1.339(4) ?
N11 C12 . 1.340(4) ?
C12 C13 . 1.374(4) ?
C13 C14 . 1.388(4) ?
C13 Br11 . 1.881(3) ?
C14 C15 . 1.398(4) ?
C15 C16 . 1.382(4) ?
C7 C8 . 1.567(4) ?
C7 Br2 . 1.931(3) y
C7 Br3 . 1.942(3) y
C7 Br4 . 1.941(3) y
C8 O2 . 1.225(4) y
C8 O1 . 1.265(4) y
C17 C18 . 1.553(4) ?
C17 Br12 . 1.937(3) y
C17 Br13 . 1.944(3) y
C17 Br14 . 1.943(3) y
C18 O12 . 1.221(3) y
C18 O11 . 1.270(4) y
N1 H01 . 0.75(3) ?
C2 H2 . 0.9500 ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
N11 H011 . 0.80(4) ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
N1 H01 O1 . 0.75(3) 1.89(4) 2.632(3) 172(4)
N11 H011 O11 . 0.80(4) 1.82(4) 2.621(4) 175(4)
C6 H6 O1 2_565 0.95 2.40 3.334(4) 168
C16 H16 O11 2_576 0.95 2.44 3.373(4) 169
C2 H2 Br13 1_545 0.95 3.05 3.939(3) 157
C12 H12 Br14 1_655 0.95 3.08 3.997(3) 163
C16 H16 Br14 2_576 0.95 3.12 3.626(3) 115
C5 H5 Br3 2_565 0.95 3.08 3.748(3) 129
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 N1 C2 C3 1.6(5) ?
N1 C2 C3 C4 -0.2(5) ?
N1 C2 C3 Br1 177.8(2) ?
C2 C3 C4 C5 -1.5(5) ?
Br1 C3 C4 C5 -179.4(2) ?
C3 C4 C5 C6 1.8(5) ?
C2 N1 C6 C5 -1.2(5) ?
C4 C5 C6 N1 -0.5(5) ?
C16 N11 C12 C13 -0.1(5) ?
N11 C12 C13 C14 0.2(5) ?
N11 C12 C13 Br11 178.3(2) ?
C12 C13 C14 C15 -0.9(5) ?
Br11 C13 C14 C15 -178.9(2) ?
C13 C14 C15 C16 1.5(5) ?
C12 N11 C16 C15 0.7(5) ?
C14 C15 C16 N11 -1.4(5) ?
Br2 C7 C8 O2 2.3(4) y
Br4 C7 C8 O2 123.0(3) ?
Br3 C7 C8 O2 -117.7(3) ?
Br2 C7 C8 O1 -178.0(2) ?
Br4 C7 C8 O1 -57.3(3) ?
Br3 C7 C8 O1 62.0(3) ?
Br12 C17 C18 O12 -1.7(4) y
Br14 C17 C18 O12 119.5(3) ?
Br13 C17 C18 O12 -121.2(3) ?
Br12 C17 C18 O11 178.3(2) ?
Br14 C17 C18 O11 -60.5(3) ?
Br13 C17 C18 O11 58.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107543
