#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/64/4506477.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_4506477
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 H14 N3 O, H2 O4 P, C H4 O '
_chemical_formula_sum            'C15 H20 N3 O6 P'
_chemical_formula_weight         369.31
_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                 94.871(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1440(11)
_cell_length_b                   19.3775(19)
_cell_length_c                   8.1560(8)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      1.83
_cell_volume                     1754.9(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18487
_diffrn_reflns_theta_full        27.20
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0482
_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)+(0.1650P)²+0.1053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                2864
_reflns_number_total             3902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300496t_si_002.cif
_cod_data_source_block           Sal-H2PO4
_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_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C15 H20 N3 O6 P '
_cod_database_code               4506477
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
P1 P 0.62050(5) 0.22165(2) 0.02299(6) 0.0383(2) Uani 1 1 d .
C1 C 0.80713(17) 0.86229(10) 0.1516(2) 0.0399(5) Uani 1 1 d .
C2 C 0.9279(2) 0.87927(11) 0.1624(3) 0.0532(6) Uani 1 1 d .
C6 C 0.7721(3) 0.80437(13) 0.2340(4) 0.0663(7) Uani 1 1 d .
H6 H 0.6911 0.7921 0.2274 0.080 Uiso 1 1 calc R
C3 C 1.0118(3) 0.83879(16) 0.2544(5) 0.0820(10) Uani 1 1 d .
H3 H 1.0932 0.8501 0.2610 0.098 Uiso 1 1 calc R
C4 C 0.9731(4) 0.78178(17) 0.3355(5) 0.0915(12) Uani 1 1 d .
H4 H 1.0288 0.7547 0.3979 0.110 Uiso 1 1 calc R
C5 C 0.8550(4) 0.76454(18) 0.3258(5) 0.0942(12) Uani 1 1 d .
H5 H 0.8299 0.7258 0.3810 0.113 Uiso 1 1 calc R
C9 C 0.41826(18) 0.98338(11) 0.2821(2) 0.0432(5) Uani 1 1 d .
C14 C 0.46032(19) 1.05053(11) 0.3030(3) 0.0433(5) Uani 1 1 d .
C13 C 0.3947(2) 1.10029(14) 0.3760(3) 0.0596(6) Uani 1 1 d .
H13 H 0.4231 1.1451 0.3918 0.072 Uiso 1 1 calc R
C10 C 0.3080(2) 0.96269(15) 0.3318(3) 0.0610(6) Uani 1 1 d .
H10 H 0.2807 0.9175 0.3187 0.073 Uiso 1 1 calc R
C12 C 0.2829(3) 1.07975(18) 0.4251(3) 0.0726(8) Uani 1 1 d .
H12 H 0.2354 1.1118 0.4744 0.087 Uiso 1 1 calc R
C11 C 0.2411(2) 1.01299(18) 0.4022(4) 0.0740(8) Uani 1 1 d .
H11 H 0.1657 1.0016 0.4351 0.089 Uiso 1 1 calc R
N3 N 0.57298(16) 1.05202(9) 0.2389(2) 0.0442(4) Uani 1 1 d .
N2 N 0.50538(16) 0.94691(9) 0.2043(2) 0.0422(4) Uani 1 1 d .
C8 C 0.59642(17) 0.98937(10) 0.1801(2) 0.0388(4) Uani 1 1 d .
N1 N 0.69543(18) 0.97282(10) 0.1090(3) 0.0504(5) Uani 1 1 d .
C7 C 0.7193(2) 0.90464(12) 0.0432(3) 0.0533(6) Uani 1 1 d .
H7A H 0.7505 0.9101 -0.0635 0.064 Uiso 1 1 calc R
H7B H 0.6439 0.8796 0.0266 0.064 Uiso 1 1 calc R
O1 O 0.95856(19) 0.93721(9) 0.0821(4) 0.0967(9) Uani 1 1 d .
H1O H 1.0172 0.9292 0.0309 0.145 Uiso 1 1 calc R
O3 O 0.68061(13) 0.17938(7) 0.16186(18) 0.0449(4) Uani 1 1 d .
O2 O 0.56443(15) 0.18255(8) -0.12116(19) 0.0559(5) Uani 1 1 d .
O5 O 0.7157(2) 0.27326(11) -0.0312(2) 0.0822(7) Uani 1 1 d .
H5O H 0.6982 0.2847 -0.1271 0.123 Uiso 1 1 calc R
O4 O 0.51553(19) 0.26383(12) 0.0900(3) 0.0791(6) Uani 1 1 d .
H4O H 0.5422 0.2878 0.1675 0.119 Uiso 1 1 calc R
O6 O 0.13887(14) 0.90953(9) 0.8781(2) 0.0669(5) Uani 1 1 d .
H6O H 0.1848 0.8764 0.8880 0.100 Uiso 1 1 calc R
C15 C 0.0673(3) 0.9048(2) 0.7251(5) 0.1020(12) Uani 1 1 d .
H15C H 0.0175 0.9450 0.7101 0.153 Uiso 1 1 calc R
H15B H 0.0174 0.8644 0.7251 0.153 Uiso 1 1 calc R
H15A H 0.1190 0.9016 0.6370 0.153 Uiso 1 1 calc R
H3N H 0.608(3) 1.0869(16) 0.223(4) 0.071(9) Uiso 1 1 d .
H2N H 0.492(2) 0.9061(13) 0.181(3) 0.051(7) Uiso 1 1 d .
H1N H 0.747(3) 1.0022(15) 0.118(3) 0.062(8) 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'
P P 0.1023 0.0942 '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
O2 P1 O3 116.50(9)
O2 P1 O5 110.75(10)
O3 P1 O5 107.08(9)
O2 P1 O4 105.40(10)
O3 P1 O4 108.62(10)
O5 P1 O4 108.24(15)
C2 C1 C6 118.5(2)
C2 C1 C7 119.3(2)
C6 C1 C7 122.1(2)
O1 C2 C1 116.7(2)
O1 C2 C3 122.8(2)
C1 C2 C3 120.5(2)
C5 C6 C1 121.1(3)
C4 C3 C2 119.2(3)
C5 C4 C3 120.8(3)
C4 C5 C6 119.9(3)
C10 C9 C14 122.2(2)
C10 C9 N2 130.9(2)
C14 C9 N2 106.84(18)
C13 C14 C9 121.6(2)
C13 C14 N3 132.3(2)
C9 C14 N3 106.10(18)
C14 C13 C12 116.3(3)
C11 C10 C9 116.2(3)
C11 C12 C13 121.7(3)
C10 C11 C12 122.0(3)
C8 N3 C14 108.86(18)
C8 N2 C9 108.78(17)
N1 C8 N2 125.86(19)
N1 C8 N3 124.7(2)
N2 C8 N3 109.41(19)
C8 N1 C7 124.3(2)
N1 C7 C1 114.01(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.4906(15)
P1 O3 1.5078(14)
P1 O5 1.5494(18)
P1 O4 1.5633(19)
C1 C2 1.381(3)
C1 C6 1.382(3)
C1 C7 1.506(3)
C2 O1 1.358(3)
C2 C3 1.391(3)
C6 C5 1.375(4)
C3 C4 1.376(5)
C4 C5 1.355(5)
C9 C10 1.385(3)
C9 C14 1.389(3)
C9 N2 1.396(3)
C14 C13 1.376(3)
C14 N3 1.401(3)
C13 C12 1.399(4)
C10 C11 1.381(4)
C12 C11 1.382(5)
N3 C8 1.339(3)
N2 C8 1.334(3)
C8 N1 1.329(3)
N1 C7 1.459(3)
O6 C15 1.426(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146127
