#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:32:27 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180477 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/46/7214654.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7214654
loop_
_publ_author_name
'Li, Wei-Liang'
'Wu, An-Kai'
'Lee, Kwang-Ming'
_publ_section_title
;
 Anion-controlled dimerized rectangular, herringbone and tape building
 blocks by L-shaped diamide-substituted pyridinium salts via N--H⋯O
 and C--H⋯O hydrogen bonding
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              6072
_journal_paper_doi               10.1039/c2ce25695a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C8 H10 Br N3 O2'
_chemical_formula_weight         260.10
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                90.00
_cell_angle_beta                 109.0290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.03600(10)
_cell_length_b                   28.8208(7)
_cell_length_c                   6.9016(2)
_cell_measurement_reflns_used    3119
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3810
_cell_measurement_theta_min      3.4277
_cell_volume                     946.97(4)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3519
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    4.318
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.5061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lamellar
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.899
_refine_diff_density_min         -1.678
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.41(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1625
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0464
_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)+(0.0809P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                1529
_reflns_number_total             1625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25695a.txt
_cod_data_source_block           br
_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               7214654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.54574(19) 0.888811(17) 0.49717(17) 0.0255(2) Uani 1 1 d .
C4 C 0.163(3) 0.1161(3) 0.384(2) 0.030(3) Uani 1 1 d .
H4 H 0.2240 0.0961 0.2977 0.036 Uiso 1 1 calc R
C5 C 0.2374(16) 0.1625(2) 0.3992(11) 0.0254(16) Uani 1 1 d .
H5 H 0.3573 0.1742 0.3291 0.030 Uiso 1 1 calc R
C6 C 0.1343(15) 0.1919(3) 0.5182(11) 0.0251(16) Uani 1 1 d .
C7 C -0.0261(15) 0.1735(2) 0.6282(12) 0.0230(15) Uani 1 1 d .
H7 H -0.0930 0.1929 0.7138 0.028 Uiso 1 1 calc R
C8 C -0.0888(17) 0.1260(4) 0.6118(14) 0.0240(18) Uani 1 1 d .
H8 H -0.1987 0.1131 0.6871 0.029 Uiso 1 1 calc R
C2 C -0.0939(15) 0.0503(2) 0.4554(12) 0.0251(15) Uani 1 1 d .
H2A H -0.2058 0.0467 0.3089 0.030 Uiso 1 1 calc R
H2B H -0.2184 0.0435 0.5370 0.030 Uiso 1 1 calc R
C1 C 0.1436(16) 0.0156(2) 0.5097(11) 0.0258(15) Uani 1 1 d .
C3 C 0.2126(15) 0.2425(2) 0.5223(11) 0.0229(14) Uani 1 1 d .
N2 N 0.0032(13) 0.0990(2) 0.4928(14) 0.0224(14) Uani 1 1 d .
N1 N 0.049(2) -0.02838(18) 0.4802(15) 0.0321(14) Uani 1 1 d .
H1B H 0.1689 -0.0516 0.5064 0.039 Uiso 1 1 calc R
H1A H -0.1328 -0.0339 0.4349 0.039 Uiso 1 1 calc R
N3 N 0.0168(13) 0.2719(2) 0.5369(10) 0.0279(17) Uani 1 1 d .
H3B H 0.0477 0.3020 0.5400 0.033 Uiso 1 1 calc R
H3A H -0.1438 0.2613 0.5436 0.033 Uiso 1 1 calc R
O1 O 0.3896(11) 0.02662(18) 0.5716(8) 0.0294(11) Uani 1 1 d .
O2 O 0.4412(11) 0.25402(17) 0.5123(9) 0.0286(11) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0211(3) 0.0292(3) 0.0278(3) -0.0010(4) 0.0102(2) -0.0007(3)
C4 0.026(5) 0.036(5) 0.032(6) 0.001(3) 0.014(4) 0.004(3)
C5 0.019(4) 0.034(4) 0.025(4) 0.003(3) 0.008(3) 0.002(3)
C6 0.015(3) 0.035(3) 0.024(4) 0.000(3) 0.005(3) 0.000(2)
C7 0.013(3) 0.031(3) 0.026(4) -0.002(3) 0.007(3) 0.001(3)
C8 0.015(4) 0.039(4) 0.023(5) 0.007(4) 0.012(3) 0.005(4)
C2 0.022(4) 0.024(3) 0.029(3) 0.004(3) 0.009(3) 0.003(3)
C1 0.027(4) 0.031(4) 0.022(3) 0.001(3) 0.012(3) 0.002(3)
C3 0.016(3) 0.032(3) 0.023(3) -0.003(3) 0.009(3) 0.000(3)
N2 0.014(4) 0.029(2) 0.028(3) 0.005(4) 0.012(3) 0.001(2)
N1 0.025(3) 0.028(2) 0.043(4) -0.002(4) 0.010(3) 0.001(4)
N3 0.016(3) 0.029(3) 0.041(5) -0.002(3) 0.013(3) -0.001(3)
O1 0.019(3) 0.035(3) 0.037(3) -0.001(2) 0.014(2) 0.003(2)
O2 0.020(3) 0.035(3) 0.035(3) 0.002(2) 0.015(2) -0.0038(19)
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
N2 C4 C5 120.3(11)
N2 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 119.2(9)
C4 C5 H5 120.4
C6 C5 H5 120.4
C7 C6 C5 119.3(7)
C7 C6 C3 123.8(7)
C5 C6 C3 116.9(7)
C6 C7 C8 119.1(7)
C6 C7 H7 120.4
C8 C7 H7 120.4
N2 C8 C7 120.7(9)
N2 C8 H8 119.6
C7 C8 H8 119.6
N2 C2 C1 113.3(6)
N2 C2 H2A 108.9
C1 C2 H2A 108.9
N2 C2 H2B 108.9
C1 C2 H2B 108.9
H2A C2 H2B 107.7
O1 C1 N1 124.8(7)
O1 C1 C2 123.2(7)
N1 C1 C2 112.0(7)
O2 C3 N3 124.6(7)
O2 C3 C6 120.4(6)
N3 C3 C6 114.9(6)
C8 N2 C4 121.3(6)
C8 N2 C2 120.3(8)
C4 N2 C2 118.0(8)
C1 N1 H1B 120.0
C1 N1 H1A 120.0
H1B N1 H1A 120.0
C3 N3 H3B 120.0
C3 N3 H3A 120.0
H3B N3 H3A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 N2 1.359(17)
C4 C5 1.384(11)
C4 H4 0.9500
C5 C6 1.392(11)
C5 H5 0.9500
C6 C7 1.381(11)
C6 C3 1.510(10)
C7 C8 1.403(14)
C7 H7 0.9500
C8 N2 1.320(13)
C8 H8 0.9500
C2 N2 1.479(9)
C2 C1 1.511(10)
C2 H2A 0.9900
C2 H2B 0.9900
C1 O1 1.214(9)
C1 N1 1.345(9)
C3 O2 1.222(9)
C3 N3 1.328(9)
N1 H1B 0.8800
N1 H1A 0.8800
N3 H3B 0.8800
N3 H3A 0.8800
