#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:51:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179600 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/64/4506472.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_4506472
loop_
_publ_author_name
'Gogoi, Abhijit'
'Das, Gopal'
_publ_section_title
;
 Charge-Assisted Complexation of Anions of Different Dimensionality by
 Benzimidazole-Based Receptors Bearing -OH Functionality
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4012
_journal_paper_doi               10.1021/cg300496t
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27
_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                 95.467(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9851(5)
_cell_length_b                   9.1493(4)
_cell_length_c                   12.1930(5)
_cell_measurement_reflns_used    8123
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      33.870
_cell_measurement_theta_min      2.79
_cell_volume                     1219.89(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.09
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22008
_diffrn_reflns_theta_full        33.87
_diffrn_reflns_theta_max         33.87
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504.0
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0611
_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)+(0.1200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1759
_refine_ls_wR_factor_ref         0.1943
_reflns_number_gt                2853
_reflns_number_total             4892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300496t_si_002.cif
_cod_data_source_block           SalL
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1219.90(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4506472
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
O1 O 0.35612(8) 1.04238(8) 0.03148(6) 0.0432(2) Uani 1 1 d .
H1O H 0.3357 1.0858 -0.0262 0.065 Uiso 1 1 calc R
C1 C 0.41085(10) 0.80428(12) 0.09225(8) 0.0379(3) Uani 1 1 d .
C2 C 0.35056(9) 0.89501(12) 0.01309(8) 0.0367(3) Uani 1 1 d .
C7 C 0.48001(11) 0.87445(13) 0.19205(9) 0.0417(3) Uani 1 1 d .
H7B H 0.5266 0.9561 0.1673 0.050 Uiso 1 1 calc R
H7A H 0.4210 0.9136 0.2387 0.050 Uiso 1 1 calc R
C8 C 0.67398(10) 0.74492(11) 0.22690(8) 0.0381(3) Uani 1 1 d .
C14 C 0.85583(11) 0.64165(13) 0.23258(9) 0.0436(3) Uani 1 1 d .
C3 C 0.28676(11) 0.83586(15) -0.08042(9) 0.0484(3) Uani 1 1 d .
H3 H 0.2477 0.8971 -0.1335 0.058 Uiso 1 1 calc R
C9 C 0.83543(11) 0.72969(12) 0.13935(9) 0.0410(3) Uani 1 1 d .
C6 C 0.40414(12) 0.65387(13) 0.07595(11) 0.0516(3) Uani 1 1 d .
H6 H 0.4434 0.5918 0.1284 0.062 Uiso 1 1 calc R
C4 C 0.28130(12) 0.68585(16) -0.09452(12) 0.0565(4) Uani 1 1 d .
H4 H 0.2377 0.6464 -0.1567 0.068 Uiso 1 1 calc R
C5 C 0.34026(13) 0.59482(16) -0.01683(13) 0.0605(4) Uani 1 1 d .
H5 H 0.3372 0.4940 -0.0267 0.073 Uiso 1 1 calc R
C10 C 0.92342(13) 0.74059(16) 0.06590(11) 0.0580(4) Uani 1 1 d .
H10 H 0.9115 0.7996 0.0037 0.070 Uiso 1 1 calc R
C13 C 0.96209(13) 0.56038(17) 0.25466(12) 0.0610(4) Uani 1 1 d .
H13 H 0.9744 0.5006 0.3164 0.073 Uiso 1 1 calc R
C11 C 1.02969(14) 0.6608(2) 0.08798(13) 0.0722(5) Uani 1 1 d .
H11 H 1.0900 0.6665 0.0395 0.087 Uiso 1 1 calc R
C12 C 1.04880(14) 0.5731(2) 0.17974(14) 0.0727(5) Uani 1 1 d .
H12 H 1.1216 0.5212 0.1918 0.087 Uiso 1 1 calc R
N2 N 0.71970(9) 0.79462(10) 0.13746(7) 0.0412(2) Uani 1 1 d .
N3 N 0.75117(9) 0.65298(11) 0.28653(8) 0.0450(3) Uani 1 1 d .
N1 N 0.56302(9) 0.77895(12) 0.25831(8) 0.0474(3) Uani 1 1 d .
H3N H 0.7311(15) 0.6125(16) 0.3478(13) 0.062(4) Uiso 1 1 d .
H1N H 0.5424(13) 0.7350(13) 0.3191(11) 0.046(3) Uiso 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 118.39(10)
C6 C1 C7 123.35(10)
C2 C1 C7 118.26(10)
O1 C2 C3 121.98(10)
O1 C2 C1 117.61(9)
C3 C2 C1 120.40(10)
N1 C7 C1 115.62(9)
N2 C8 N1 125.36(10)
N2 C8 N3 112.83(10)
N1 C8 N3 121.81(10)
N3 C14 C13 132.07(12)
N3 C14 C9 105.58(10)
C13 C14 C9 122.31(12)
C4 C3 C2 120.04(12)
C10 C9 C14 120.14(11)
C10 C9 N2 130.38(11)
C14 C9 N2 109.48(10)
C5 C6 C1 121.27(12)
C5 C4 C3 120.18(12)
C4 C5 C6 119.71(12)
C11 C10 C9 117.76(13)
C12 C13 C14 116.41(14)
C12 C11 C10 121.80(14)
C11 C12 C13 121.58(14)
C8 N2 C9 104.81(9)
C8 N3 C14 107.30(9)
C8 N1 C7 121.19(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3673(13)
C1 C6 1.3914(16)
C1 C2 1.3920(15)
C1 C7 1.5145(16)
C2 C3 1.3898(15)
C7 N1 1.4517(15)
C8 N2 1.3238(13)
C8 N1 1.3484(15)
C8 N3 1.3556(15)
C14 N3 1.3819(16)
C14 C13 1.3886(18)
C14 C9 1.3938(16)
C3 C4 1.3839(19)
C9 C10 1.3824(17)
C9 N2 1.4015(15)
C6 C5 1.3830(19)
C4 C5 1.376(2)
C10 C11 1.381(2)
C13 C12 1.386(2)
C11 C12 1.376(2)
