#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:18:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179571 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/36/4503603.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_4503603
loop_
_publ_author_name
'Custelcean, Radu'
'Jiang, De-en'
'Hay, Benjamin P.'
'Luo, Wensui'
'Gu, Baohua'
_publ_section_title
;
 Hydrogen-Bonded Helices for Anion Binding and Separation
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1909
_journal_paper_doi               10.1021/cg800137e
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C11 H11 Br N4 O'
_chemical_formula_weight         295.15
_chemical_name_common            1-HBr
_chemical_name_systematic
; 
 ? 
;
_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                90.00
_cell_angle_beta                 102.711(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8359(14)
_cell_length_b                   7.6971(9)
_cell_length_c                   13.3409(16)
_cell_measurement_temperature    173(2)
_cell_volume                     1185.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14585
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    3.456
_exptl_absorpt_correction_T_max  0.8741
_exptl_absorpt_correction_T_min  0.3862
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0293
_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)+(0.0508P)²+0.2280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0809
_reflns_number_gt                2456
_reflns_number_total             2951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800137e-file001.cif
_cod_data_source_block           1-HBr
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4503603
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_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 0.827525(16) 0.12451(3) 0.404401(13) 0.02700(9) Uani 1 1 d .
O1 O 0.57375(13) 0.11379(18) 0.67089(11) 0.0275(3) Uani 1 1 d .
N1 N 0.83239(14) -0.1206(2) 0.88263(14) 0.0245(3) Uani 1 1 d .
H1N H 0.8041 -0.1336 0.9379 0.029 Uiso 1 1 calc R
C1 C 0.76657(16) -0.0425(2) 0.80080(14) 0.0231(4) Uani 1 1 d .
H1 H 0.6917 -0.0012 0.8037 0.028 Uiso 1 1 calc R
N2 N 0.74497(14) 0.0585(2) 0.62324(12) 0.0248(3) Uani 1 1 d .
H2N H 0.7809 0.0735 0.5727 0.030 Uiso 1 1 calc R
C2 C 0.80740(16) -0.0216(2) 0.71143(14) 0.0214(4) Uani 1 1 d .
N3 N 0.59482(14) 0.1777(2) 0.50845(12) 0.0233(3) Uani 1 1 d .
H3N H 0.6421 0.1637 0.4666 0.028 Uiso 1 1 calc R
C3 C 0.91876(18) -0.0833(3) 0.71113(16) 0.0252(4) Uani 1 1 d .
H3 H 0.9492 -0.0719 0.6513 0.030 Uiso 1 1 calc R
N4 N 0.30020(16) 0.3599(2) 0.47624(14) 0.0276(4) Uani 1 1 d .
C4 C 0.98415(18) -0.1610(3) 0.79857(18) 0.0290(4) Uani 1 1 d .
H4 H 1.0601 -0.2011 0.7989 0.035 Uiso 1 1 calc R
C5 C 0.93965(18) -0.1802(3) 0.88481(18) 0.0312(5) Uani 1 1 d .
H5 H 0.9838 -0.2345 0.9447 0.037 Uiso 1 1 calc R
C6 C 0.63215(18) 0.1169(2) 0.60689(14) 0.0210(4) Uani 1 1 d .
C7 C 0.39893(17) 0.2775(3) 0.51884(14) 0.0247(4) Uani 1 1 d .
H7 H 0.4077 0.2297 0.5858 0.030 Uiso 1 1 calc R
C8 C 0.48903(16) 0.2599(2) 0.46776(13) 0.0207(4) Uani 1 1 d .
C9 C 0.47340(18) 0.3270(3) 0.36862(14) 0.0252(4) Uani 1 1 d .
H9 H 0.5323 0.3140 0.3310 0.030 Uiso 1 1 calc R
C10 C 0.3716(2) 0.4124(3) 0.32540(16) 0.0306(5) Uani 1 1 d .
H10 H 0.3599 0.4602 0.2583 0.037 Uiso 1 1 calc R
C11 C 0.2873(2) 0.4268(3) 0.38160(16) 0.0309(5) Uani 1 1 d .
H11 H 0.2176 0.4864 0.3523 0.037 Uiso 1 1 calc R
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 C5 123.32(19)
N1 C1 C2 120.15(18)
C6 N2 C2 126.49(16)
N2 C2 C1 123.87(17)
N2 C2 C3 118.26(17)
C1 C2 C3 117.86(18)
C6 N3 C8 126.64(16)
C4 C3 C2 119.69(19)
C11 N4 C7 119.24(19)
C5 C4 C3 120.34(19)
N1 C5 C4 118.62(19)
O1 C6 N3 124.59(18)
O1 C6 N2 124.37(17)
N3 C6 N2 111.04(17)
N4 C7 C8 121.87(18)
C7 C8 C9 118.20(17)
C7 C8 N3 124.70(16)
C9 C8 N3 117.10(17)
C10 C9 C8 119.57(19)
C11 C10 C9 118.70(19)
N4 C11 C10 122.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.211(2)
N1 C1 1.336(2)
N1 C5 1.344(3)
C1 C2 1.391(3)
N2 C6 1.380(2)
N2 C2 1.388(2)
C2 C3 1.402(3)
N3 C6 1.372(2)
N3 C8 1.401(2)
C3 C4 1.386(3)
N4 C11 1.341(3)
N4 C7 1.341(3)
C4 C5 1.375(3)
C7 C8 1.393(3)
C8 C9 1.394(3)
C9 C10 1.382(3)
C10 C11 1.378(3)
