#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:01:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180408 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/77/7207762.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_7207762
loop_
_publ_author_name
'Wu, An-Kai'
'Lee, Kwang-Ming'
_publ_section_title
;
 Self-assembly of seven diamide-containing pyridinium salts via
 nonconventional C--H⋯O hydrogen bonding catemers
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              3424
_journal_paper_doi               10.1039/c2ce06448k
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 114.243(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3283(8)
_cell_length_b                   8.1976(7)
_cell_length_c                   12.3290(9)
_cell_measurement_reflns_used    5398
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3569
_cell_measurement_theta_min      3.0755
_cell_volume                     951.81(13)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7935
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    4.296
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.7754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0168
_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)+(0.0172P)²+0.8088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0420
_reflns_number_gt                1832
_reflns_number_total             1937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06448k.txt
_cod_data_source_block           838305
_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               7207762
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.756031(16) 0.892408(19) 0.905524(13) 0.01267(6) Uani 1 1 d .
O1 O 0.10833(12) 0.64526(14) 0.68310(10) 0.0149(2) Uani 1 1 d .
O2 O 0.57406(12) 0.43667(14) 1.15911(10) 0.0127(2) Uani 1 1 d .
N1 N 0.13794(15) 0.40814(17) 0.60015(12) 0.0153(3) Uani 1 1 d .
H1A H 0.1354 0.4561 0.5354 0.018 Uiso 1 1 calc R
H1B H 0.1493 0.3018 0.6084 0.018 Uiso 1 1 calc R
N2 N 0.16935(13) 0.48606(16) 0.89904(11) 0.0098(3) Uani 1 1 d .
N3 N 0.49898(14) 0.50962(17) 1.30113(11) 0.0137(3) Uani 1 1 d .
H3A H 0.5794 0.4809 1.3598 0.016 Uiso 1 1 calc R
H3B H 0.4295 0.5500 1.3167 0.016 Uiso 1 1 calc R
C1 C 0.12461(16) 0.4965(2) 0.68564(13) 0.0117(3) Uani 1 1 d .
C2 C 0.12527(17) 0.39147(19) 0.78845(13) 0.0116(3) Uani 1 1 d .
H2B H 0.0289 0.3469 0.7676 0.014 Uiso 1 1 calc R
H2A H 0.1910 0.2985 0.8009 0.014 Uiso 1 1 calc R
C3 C 0.29648(16) 0.45556(19) 0.98757(13) 0.0097(3) Uani 1 1 d .
H3 H 0.3571 0.3759 0.9771 0.012 Uiso 1 1 calc R
C4 C 0.33980(16) 0.53962(19) 1.09421(13) 0.0099(3) Uani 1 1 d .
C5 C 0.48243(16) 0.49199(19) 1.18869(13) 0.0108(3) Uani 1 1 d .
C6 C 0.25125(17) 0.6577(2) 1.10741(14) 0.0131(3) Uani 1 1 d .
H6 H 0.2797 0.7173 1.1796 0.016 Uiso 1 1 calc R
C7 C 0.11992(17) 0.6884(2) 1.01368(14) 0.0133(3) Uani 1 1 d .
H7 H 0.0585 0.7694 1.0214 0.016 Uiso 1 1 calc R
C8 C 0.08044(17) 0.60013(19) 0.91012(14) 0.0123(3) Uani 1 1 d .
H8 H -0.0092 0.6191 0.8463 0.015 Uiso 1 1 calc R
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 0.01182(9) 0.01403(10) 0.01304(9) -0.00073(6) 0.00601(6) -0.00147(6)
O1 0.0159(6) 0.0117(6) 0.0155(6) 0.0026(4) 0.0048(5) 0.0009(4)
O2 0.0118(5) 0.0133(5) 0.0134(5) 0.0013(4) 0.0056(4) 0.0014(4)
N1 0.0200(7) 0.0143(7) 0.0125(6) 0.0016(5) 0.0077(6) 0.0011(6)
N2 0.0112(6) 0.0091(6) 0.0093(6) 0.0010(5) 0.0043(5) -0.0009(5)
N3 0.0104(6) 0.0189(7) 0.0101(6) 0.0007(5) 0.0026(5) 0.0034(5)
C1 0.0069(7) 0.0159(8) 0.0098(7) 0.0013(6) 0.0010(6) -0.0011(6)
C2 0.0133(7) 0.0114(8) 0.0095(7) -0.0014(6) 0.0040(6) -0.0017(6)
C3 0.0103(7) 0.0079(7) 0.0125(7) 0.0032(6) 0.0063(6) 0.0002(6)
C4 0.0102(7) 0.0094(7) 0.0108(7) 0.0026(6) 0.0048(6) -0.0014(6)
C5 0.0122(7) 0.0078(7) 0.0117(7) 0.0007(6) 0.0043(6) -0.0022(6)
C6 0.0173(8) 0.0105(8) 0.0127(7) 0.0006(6) 0.0074(6) -0.0010(6)
C7 0.0142(8) 0.0115(8) 0.0158(8) 0.0020(6) 0.0076(6) 0.0036(6)
C8 0.0104(7) 0.0129(8) 0.0134(7) 0.0037(6) 0.0048(6) 0.0014(6)
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
C1 N1 H1A 120.0
C1 N1 H1B 120.0
H1A N1 H1B 120.0
C3 N2 C8 121.56(13)
C3 N2 C2 118.91(13)
C8 N2 C2 119.53(13)
C5 N3 H3A 120.0
C5 N3 H3B 120.0
H3A N3 H3B 120.0
O1 C1 N1 125.24(14)
O1 C1 C2 122.23(14)
N1 C1 C2 112.49(14)
N2 C2 C1 111.47(13)
N2 C2 H2B 109.3
C1 C2 H2B 109.3
N2 C2 H2A 109.3
C1 C2 H2A 109.3
H2B C2 H2A 108.0
N2 C3 C4 120.39(14)
N2 C3 H3 119.8
C4 C3 H3 119.8
C3 C4 C6 119.14(14)
C3 C4 C5 115.91(13)
C6 C4 C5 124.95(14)
O2 C5 N3 124.17(14)
O2 C5 C4 119.51(13)
N3 C5 C4 116.30(13)
C4 C6 C7 119.46(15)
C4 C6 H6 120.3
C7 C6 H6 120.3
C8 C7 C6 119.35(15)
C8 C7 H7 120.3
C6 C7 H7 120.3
N2 C8 C7 120.09(14)
N2 C8 H8 120.0
C7 C8 H8 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.229(2)
O2 C5 1.2320(19)
N1 C1 1.332(2)
N1 H1A 0.8800
N1 H1B 0.8800
N2 C3 1.342(2)
N2 C8 1.356(2)
N2 C2 1.4690(19)
N3 C5 1.333(2)
N3 H3A 0.8800
N3 H3B 0.8800
C1 C2 1.530(2)
C2 H2B 0.9900
C2 H2A 0.9900
C3 C4 1.386(2)
C3 H3 0.9500
C4 C6 1.387(2)
C4 C5 1.507(2)
C6 C7 1.397(2)
C6 H6 0.9500
C7 C8 1.376(2)
C7 H7 0.9500
C8 H8 0.9500
