#------------------------------------------------------------------------------
#$Date: 2018-09-23 18:18:48 +0300 (Sun, 23 Sep 2018) $
#$Revision: 211127 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/46/4504653.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_4504653
loop_
_publ_author_name
'Bhogala, Balakrishna R.'
'Nangia, Ashwini'
_publ_section_title
;
 Influence of the Ammonium Cation and 18-Crown-6 Guest on the
 Supramolecular Networks of 1,3,5-Cyclohexanetricarboxylic Acid
;
_journal_coden_ASTM              CGDEFU
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              32
_journal_page_last               35
_journal_paper_doi               10.1021/cg050396w
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         '1/6(C9 H12 O6),1/12(C12 H24 O6)'
_chemical_formula_sum            'C2.5 H4 O1.5'
_chemical_formula_weight         58.06
_chemical_melting_point          433
_chemical_name_systematic
; 
 cis,cis-1,3,5-cyclohexanetricarboxylic acid - 18-crown-6 
;
_space_group_IT_number           166
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3 2"'
_symmetry_space_group_name_H-M   'R -3 m :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            36
_cell_length_a                   16.5374(8)
_cell_length_b                   16.5374(8)
_cell_length_c                   11.5830(11)
_cell_measurement_reflns_used    536
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.26
_cell_volume                     2743.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT Plus'
_computing_molecular_graphics    'PLUTON (Spek, 1992)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3396
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0540
_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)+(0.0643P)²+1.6660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                443
_reflns_number_total             670
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050396wsi20050809_044026.cif
_cod_data_source_block           an312_m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Rhombohedral' changed to
'rhombohedral' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'R -3 m'
_cod_original_formula_sum        'C2.50 H4 O1.50'
_cod_database_code               4504653
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
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
O2 O 0.90146(7) 0.09854(7) 0.4807(2) 0.0677(7) Uani 1 2 d S
C6 C 0.80948(14) 0.04853(15) 0.5236(2) 0.0725(8) Uani 1 1 d .
H6A H 0.7756 0.0800 0.5017 0.087 Uiso 1 1 calc R
H6B H 0.8108 0.0464 0.6073 0.087 Uiso 1 1 calc R
C4 C 0.10094(17) 0.05047(8) 0.2223(3) 0.0458(8) Uani 1 2 d S
H4 H 0.0976 0.0488 0.3068 0.055 Uiso 1 2 calc SR
C5 C 0.05084(9) -0.05084(9) 0.1813(3) 0.0470(8) Uani 1 2 d S
H5A H 0.0824 -0.0824 0.2115 0.056 Uiso 1 2 calc SR
H5B H 0.0526 -0.0526 0.0976 0.056 Uiso 1 2 calc SR
O1 O 0.24363(10) 0.18796(9) 0.18252(19) 0.0876(8) Uani 1 1 d .
C3 C 0.20241(18) 0.10120(9) 0.1911(3) 0.0527(8) Uani 1 2 d S
H1 H 0.3333 0.226(2) 0.1667 0.146(16) Uiso 1 2 d S
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
O2 0.0619(11) 0.0619(11) 0.0887(18) -0.0075(6) 0.0075(6) 0.0379(12)
C6 0.0606(15) 0.0878(18) 0.092(2) 0.0078(15) 0.0085(13) 0.0544(13)
C4 0.0335(14) 0.0372(11) 0.065(2) 0.0012(6) 0.0025(13) 0.0167(7)
C5 0.0349(11) 0.0349(11) 0.073(2) -0.0003(6) 0.0003(6) 0.0188(12)
O1 0.0376(9) 0.0387(9) 0.181(2) 0.0178(10) 0.0195(10) 0.0152(7)
C3 0.0363(15) 0.0368(11) 0.085(2) 0.0009(7) 0.0017(15) 0.0182(7)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 O2 C6 112.8(2) 22_665 .
O2 C6 C6 110.09(18) . 5_556
O2 C6 H6A 109.6 . .
C6 C6 H6A 109.6 5_556 .
O2 C6 H6B 109.6 . .
C6 C6 H6B 109.6 5_556 .
H6A C6 H6B 108.2 . .
C3 C4 C5 112.40(15) . 2
C3 C4 C5 112.40(15) . .
C5 C4 C5 111.4(3) 2 .
C3 C4 H4 106.7 . .
C5 C4 H4 106.7 2 .
C5 C4 H4 106.7 . .
C4 C5 C4 110.2(2) . 3
C4 C5 H5A 109.6 . .
C4 C5 H5A 109.6 3 .
C4 C5 H5B 109.6 . .
C4 C5 H5B 109.6 3 .
H5A C5 H5B 108.1 . .
C3 O1 H1 113.5(17) . .
O1 C3 O1 122.6(3) 24 .
O1 C3 C4 118.60(13) 24 .
O1 C3 C4 118.60(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C6 1.410(2) 22_665
O2 C6 1.410(2) .
C6 C6 1.494(4) 5_556
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C4 C3 1.497(3) .
C4 C5 1.527(2) 2
C4 C5 1.527(2) .
C4 H4 0.9800 .
C5 C4 1.527(2) 3
C5 H5A 0.9700 .
C5 H5B 0.9700 .
O1 C3 1.2470(18) .
O1 H1 1.303(4) .
C3 O1 1.2469(18) 24
