#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/18/7221861.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_7221861
loop_
_publ_author_name
'Singh, Amanpreet'
'Singh, Ajnesh'
'Singh, Narinder'
'Jang, Doo Ok'
_publ_section_title
;
 A benzimidazolium-based organic trication: a selective fluorescent sensor
 for detecting cysteine in water
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA14501E
_journal_year                    2015
_chemical_formula_moiety         'C11 H15 Br3 N2 O'
_chemical_formula_sum            'C11 H15 Br3 N2 O'
_chemical_formula_weight         430.98
_chemical_melting_point          ?
_chemical_name_common            R1
_chemical_name_systematic        ns44
_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_block_doi                 10.5517/cc13vvqj
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-28 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.512(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2281(8)
_cell_length_b                   8.6541(7)
_cell_length_c                   16.8320(14)
_cell_measurement_reflns_used    850
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.65
_cell_volume                     1485.3(2)
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'APEX2 (Bruker, 2007)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker KAPPA APEXII'
_diffrn_measurement_method       'combination of 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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46209
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    8.135
_exptl_absorpt_correction_T_max  0.085
_exptl_absorpt_correction_T_min  0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flackes
_exptl_crystal_F_000             832
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         1.012
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0315
_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)+(0.0326P)²+2.4365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                2535
_reflns_number_total             2918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra14501e2.cif
_cod_data_source_block           ns44
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7221861
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 0.12474(4) 0.06581(4) 0.21538(2) 0.04749(11) Uani 1 1 d .
Br2 Br 0.48034(4) 0.14302(5) 0.27356(3) 0.06092(13) Uani 1 1 d .
Br3 Br 0.46589(4) -0.24715(8) 0.46122(4) 0.09118(19) Uani 1 1 d .
N1 N 0.7762(2) 0.0583(3) 0.35665(14) 0.0348(5) Uani 1 1 d .
N2 N 0.7669(2) -0.1287(3) 0.44255(15) 0.0359(5) Uani 1 1 d .
C1 C 0.7451(3) -0.0891(4) 0.36673(19) 0.0376(7) Uani 1 1 d .
H1A H 0.7126 -0.1550 0.3262 0.045 Uiso 1 1 calc R
C2 C 0.8146(3) -0.0002(4) 0.48538(18) 0.0342(6) Uani 1 1 d .
C3 C 0.8534(3) 0.0202(4) 0.56546(18) 0.0417(7) Uani 1 1 d .
H3A H 0.8503 -0.0599 0.6021 0.050 Uiso 1 1 calc R
C4 C 0.8966(3) 0.1650(4) 0.5876(2) 0.0473(8) Uani 1 1 d .
H4A H 0.9232 0.1837 0.6408 0.057 Uiso 1 1 calc R
C5 C 0.9019(3) 0.2856(4) 0.5325(2) 0.0468(8) Uani 1 1 d .
H5A H 0.9320 0.3820 0.5502 0.056 Uiso 1 1 calc R
C6 C 0.8639(3) 0.2657(4) 0.4531(2) 0.0401(7) Uani 1 1 d .
H6A H 0.8676 0.3457 0.4165 0.048 Uiso 1 1 calc R
C7 C 0.8199(3) 0.1193(4) 0.43084(17) 0.0331(6) Uani 1 1 d .
C8 C 0.7617(3) 0.1440(4) 0.28155(19) 0.0437(7) Uani 1 1 d .
H8A H 0.7514 0.0712 0.2377 0.052 Uiso 1 1 calc R
H8B H 0.8409 0.2030 0.2757 0.052 Uiso 1 1 calc R
C9 C 0.6466(3) 0.2517(4) 0.2767(2) 0.0493(8) Uani 1 1 d .
H9A H 0.6488 0.3149 0.2293 0.059 Uiso 1 1 calc R
H9B H 0.6537 0.3200 0.3226 0.059 Uiso 1 1 calc R
C10 C 0.7448(3) -0.2824(4) 0.4754(2) 0.0453(8) Uani 1 1 d .
H10A H 0.8224 -0.3137 0.5084 0.054 Uiso 1 1 calc R
H10B H 0.7318 -0.3558 0.4319 0.054 Uiso 1 1 calc R
C11 C 0.6290(4) -0.2875(5) 0.5240(2) 0.0589(10) Uani 1 1 d .
H11A H 0.6405 -0.2115 0.5663 0.071 Uiso 1 1 calc R
H11B H 0.6245 -0.3886 0.5485 0.071 Uiso 1 1 calc R
O1 O 0.8547(3) -0.1357(4) 0.16128(18) 0.0699(8) Uani 1 1 d .
H1W H 0.8583 -0.2101 0.1946 0.076(15) Uiso 1 1 d R
H2W H 0.9174 -0.0787 0.1724 0.093(19) Uiso 1 1 d 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 0.0546(2) 0.04069(19) 0.0468(2) 0.00329(14) 0.00148(14) 0.00190(15)
Br2 0.0482(2) 0.0617(3) 0.0712(3) 0.00780(19) -0.00577(18) -0.00515(17)
Br3 0.0443(2) 0.1240(5) 0.1054(4) 0.0024(3) 0.0074(2) -0.0035(3)
N1 0.0374(13) 0.0355(13) 0.0313(12) -0.0018(10) 0.0010(10) 0.0025(11)
N2 0.0364(13) 0.0310(13) 0.0402(14) -0.0009(11) 0.0031(11) 0.0007(10)
C1 0.0351(15) 0.0382(16) 0.0392(16) -0.0061(13) 0.0024(12) 0.0029(13)
C2 0.0273(13) 0.0366(15) 0.0388(15) -0.0012(13) 0.0040(11) 0.0020(12)
C3 0.0413(17) 0.0499(19) 0.0337(16) 0.0033(14) 0.0017(13) 0.0009(14)
C4 0.0463(18) 0.061(2) 0.0341(16) -0.0068(15) -0.0017(14) -0.0030(16)
C5 0.0447(18) 0.0457(19) 0.0495(19) -0.0114(16) 0.0011(15) -0.0088(15)
C6 0.0400(16) 0.0373(16) 0.0432(17) 0.0003(13) 0.0049(13) -0.0032(13)
C7 0.0283(14) 0.0384(16) 0.0325(14) -0.0032(12) 0.0021(11) 0.0025(12)
C8 0.0494(18) 0.0482(19) 0.0333(16) 0.0035(14) 0.0026(14) -0.0029(15)
C9 0.0496(19) 0.0423(18) 0.054(2) 0.0074(15) -0.0112(16) -0.0062(15)
C10 0.0460(18) 0.0331(16) 0.057(2) 0.0044(15) 0.0053(15) 0.0003(14)
C11 0.058(2) 0.062(2) 0.058(2) 0.0068(19) 0.0104(18) -0.0120(19)
O1 0.082(2) 0.0595(18) 0.0660(18) -0.0011(15) -0.0073(15) -0.0104(16)
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 C7 108.2(3)
C1 N1 C8 126.0(3)
C7 N1 C8 125.8(3)
C1 N2 C2 108.5(3)
C1 N2 C10 125.5(3)
C2 N2 C10 126.0(3)
N2 C1 N1 110.4(3)
C3 C2 C7 121.7(3)
C3 C2 N2 131.8(3)
C7 C2 N2 106.4(3)
C4 C3 C2 116.2(3)
C3 C4 C5 122.0(3)
C6 C5 C4 121.9(3)
C5 C6 C7 116.0(3)
C2 C7 C6 122.1(3)
C2 C7 N1 106.5(3)
C6 C7 N1 131.4(3)
N1 C8 C9 112.8(3)
C8 C9 Br2 112.5(2)
N2 C10 C11 112.8(3)
C10 C11 Br3 112.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C9 1.941(3)
Br3 C11 1.936(4)
N1 C1 1.328(4)
N1 C7 1.396(4)
N1 C8 1.463(4)
N2 C1 1.323(4)
N2 C2 1.393(4)
N2 C10 1.464(4)
C2 C3 1.386(4)
C2 C7 1.386(4)
C3 C4 1.371(5)
C4 C5 1.400(5)
C5 C6 1.372(5)
C6 C7 1.387(4)
C8 C9 1.498(5)
C10 C11 1.492(5)
