#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/88/4508876.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4508876
loop_
_publ_author_name
'Pigge, F. Christopher'
'Dighe, Mayuri K.'
'Rath, Nigam P.'
_publ_section_title
;
 Self-Assembly of Sticky TABs:  Inclusion Complexes and Hydrates
 from 1,3,5-Tris(4-hydroxybenzoyl)benzene
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2732
_journal_paper_doi               10.1021/cg0604226
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C22 H20 O6'
_chemical_formula_weight         380.38
_space_group_IT_number           161
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :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            18
_cell_length_a                   17.6686(1)
_cell_length_b                   17.66860(1)
_cell_length_c                   32.0818(6)
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      2.31
_cell_volume                     8673.49(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, 2003)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, 2003)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, 2003)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, 2003)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            17786
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       spherical
_exptl_crystal_F_000             3600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0787
_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)+(0.1158P)²+26.6153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2375
_reflns_number_gt                2456
_reflns_number_total             3729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0604226sup1.cif
_cod_data_source_block           p10404
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        8673.48(18)
_cod_original_sg_symbol_H-M      R3c
_cod_database_code               4508876
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'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+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'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+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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 0.2324(2) 0.1083(3) 0.02433(14) 0.0493(11) Uani 1 1 d .
O2 O 0.3414(3) 0.4402(3) 0.13514(16) 0.0686(14) Uani 1 1 d .
H2 H 0.3115 0.4376 0.1560 0.103 Uiso 1 1 calc R
O1' O 0.5456(2) 0.1008(2) 0.03101(12) 0.0384(9) Uani 1 1 d .
O2' O 0.2104(2) 0.0117(2) 0.13503(13) 0.0456(10) Uani 1 1 d .
H2' H 0.2144 0.0402 0.1567 0.068 Uiso 1 1 calc R
C1 C 0.0612(3) -0.0276(3) 0.04702(16) 0.0324(11) Uani 1 1 d .
H1 H 0.1031 -0.0462 0.0465 0.039 Uiso 1 1 calc R
C2 C 0.0888(3) 0.0618(3) 0.04741(15) 0.0319(11) Uani 1 1 d .
C3 C 0.1854(3) 0.1259(3) 0.04610(16) 0.0333(11) Uani 1 1 d .
C4 C 0.2237(3) 0.2070(3) 0.06956(16) 0.0312(11) Uani 1 1 d .
C5 C 0.1801(3) 0.2193(3) 0.10304(16) 0.0348(12) Uani 1 1 d .
H5 H 0.1234 0.1737 0.1105 0.042 Uiso 1 1 calc R
C6 C 0.2179(3) 0.2965(3) 0.12538(17) 0.0392(13) Uani 1 1 d .
H6 H 0.1877 0.3041 0.1480 0.047 Uiso 1 1 calc R
C7 C 0.3006(4) 0.3627(3) 0.11433(19) 0.0439(14) Uani 1 1 d .
C8 C 0.3468(4) 0.3512(4) 0.08200(19) 0.0493(15) Uani 1 1 d .
H8 H 0.4046 0.3958 0.0756 0.059 Uiso 1 1 calc R
C9 C 0.3075(3) 0.2745(4) 0.05940(18) 0.0429(14) Uani 1 1 d .
H9 H 0.3379 0.2674 0.0367 0.051 Uiso 1 1 calc R
C1' C 0.6869(3) 0.2664(3) 0.05124(14) 0.0265(10) Uani 1 1 d .
H1' H 0.7004 0.2206 0.0513 0.032 Uiso 1 1 calc R
C2' C 0.5991(3) 0.2464(3) 0.05121(14) 0.0280(11) Uani 1 1 d .
C3' C 0.5305(3) 0.1516(3) 0.05062(15) 0.0307(11) Uani 1 1 d .
C4' C 0.4473(3) 0.1195(3) 0.07266(15) 0.0299(11) Uani 1 1 d .
C5' C 0.3784(3) 0.0362(3) 0.06259(17) 0.0358(12) Uani 1 1 d .
H5' H 0.3858 0.0037 0.0410 0.043 Uiso 1 1 calc R
C6' C 0.2994(3) 0.0007(4) 0.08381(18) 0.0397(13) Uani 1 1 d .
H6' H 0.2528 -0.0557 0.0767 0.048 Uiso 1 1 calc R
C7' C 0.2891(3) 0.0485(3) 0.11570(16) 0.0342(11) Uani 1 1 d .
C8' C 0.3583(3) 0.1313(3) 0.12632(16) 0.0348(12) Uani 1 1 d .
H8' H 0.3514 0.1638 0.1481 0.042 Uiso 1 1 calc R
C9' C 0.4357(3) 0.1652(3) 0.10520(16) 0.0320(11) Uani 1 1 d .
H9' H 0.4826 0.2210 0.1128 0.038 Uiso 1 1 calc R
O1S O 0.5052(12) 0.7076(8) -0.0276(5) 0.237(8) Uani 1 1 d .
O2S O 0.5386(7) 0.7325(7) 0.0411(3) 0.153(3) Uani 1 1 d .
C1S C 0.6322(13) 0.8372(11) -0.0033(6) 0.179(3) Uani 1 1 d .
H1S1 H 0.6654 0.8323 -0.0266 0.268 Uiso 1 1 calc R
H1S2 H 0.6672 0.8519 0.0222 0.268 Uiso 1 1 calc R
H1S3 H 0.6182 0.8832 -0.0094 0.268 Uiso 1 1 calc R
C2S C 0.5519(16) 0.7546(14) 0.0023(7) 0.179(3) Uani 1 1 d .
C3S C 0.4564(13) 0.6494(11) 0.0481(5) 0.179(3) Uani 1 1 d .
H3S1 H 0.4585 0.5982 0.0370 0.214 Uiso 1 1 calc R
H3S2 H 0.4046 0.6504 0.0371 0.214 Uiso 1 1 calc R
C4S C 0.4620(13) 0.6548(11) 0.0996(5) 0.179(3) Uani 1 1 d .
H4S1 H 0.4812 0.6150 0.1101 0.268 Uiso 1 1 calc R
H4S2 H 0.4043 0.6379 0.1111 0.268 Uiso 1 1 calc R
H4S3 H 0.5040 0.7147 0.1081 0.268 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'
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
C2 C1 C2 120.2(5) 3
C1 C2 C1 119.8(5) 2
C1 C2 C3 121.9(4) 2
C1 C2 C3 118.3(4) .
O1 C3 C4 120.0(5) .
O1 C3 C2 118.5(5) .
C4 C3 C2 121.5(4) .
C9 C4 C5 118.5(5) .
C9 C4 C3 119.5(4) .
C5 C4 C3 122.0(4) .
C6 C5 C4 121.2(5) .
C5 C6 C7 119.1(5) .
O2 C7 C6 121.9(5) .
O2 C7 C8 117.2(5) .
C6 C7 C8 120.9(5) .
C9 C8 C7 119.4(5) .
C8 C9 C4 120.8(5) .
C2' C1' C2' 120.0(5) 2_655
C1' C2' C1' 120.0(5) 3_665
C1' C2' C3' 123.0(4) 3_665
C1' C2' C3' 117.0(4) .
O1' C3' C4' 120.4(4) .
O1' C3' C2' 118.3(4) .
C4' C3' C2' 121.4(4) .
C9' C4' C5' 118.6(4) .
C9' C4' C3' 123.1(4) .
C5' C4' C3' 118.2(4) .
C6' C5' C4' 120.7(5) .
C5' C6' C7' 119.4(5) .
O2' C7' C6' 117.3(4) .
O2' C7' C8' 122.6(4) .
C6' C7' C8' 120.1(4) .
C9' C8' C7' 119.7(4) .
C8' C9' C4' 121.5(4) .
C2S O2S C3S 112.8(16) .
O1S C2S O2S 125(2) .
O1S C2S C1S 123.7(19) .
O2S C2S C1S 111(2) .
O2S C3S C4S 95.4(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.239(6) .
O2 C7 1.362(7) .
O1' C3' 1.229(6) .
O2' C7' 1.356(6) .
C1 C2 1.383(7) 3
C1 C2 1.400(7) .
C2 C1 1.383(7) 2
C2 C3 1.505(7) .
C3 C4 1.452(7) .
C4 C9 1.399(7) .
C4 C5 1.400(7) .
C5 C6 1.382(7) .
C6 C7 1.385(8) .
C7 C8 1.395(8) .
C8 C9 1.380(8) .
C1' C2' 1.385(6) 2_655
C1' C2' 1.409(6) .
C2' C1' 1.385(6) 3_665
C2' C3' 1.497(7) .
C3' C4' 1.466(7) .
C4' C9' 1.396(7) .
C4' C5' 1.400(7) .
C5' C6' 1.389(7) .
C6' C7' 1.395(7) .
C7' C8' 1.401(7) .
C8' C9' 1.367(7) .
O1S C2S 1.27(2) .
O2S C2S 1.29(2) .
O2S C3S 1.478(18) .
C1S C2S 1.45(2) .
C3S C4S 1.65(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C1 -1.8(10) 3 2
C2 C1 C2 C3 -178.8(3) 3 .
C1 C2 C3 O1 -139.6(5) 2 .
C1 C2 C3 O1 37.4(7) . .
C1 C2 C3 C4 40.3(7) 2 .
C1 C2 C3 C4 -142.8(5) . .
O1 C3 C4 C9 16.7(8) . .
C2 C3 C4 C9 -163.1(5) . .
O1 C3 C4 C5 -161.5(5) . .
C2 C3 C4 C5 18.6(8) . .
C9 C4 C5 C6 0.9(8) . .
C3 C4 C5 C6 179.2(5) . .
C4 C5 C6 C7 -0.1(8) . .
C5 C6 C7 O2 -180.0(6) . .
C5 C6 C7 C8 -2.0(9) . .
O2 C7 C8 C9 -178.6(6) . .
C6 C7 C8 C9 3.3(9) . .
C7 C8 C9 C4 -2.5(9) . .
C5 C4 C9 C8 0.4(8) . .
C3 C4 C9 C8 -177.9(5) . .
C2' C1' C2' C1' -0.1(9) 2_655 3_665
C2' C1' C2' C3' 179.1(3) 2_655 .
C1' C2' C3' O1' 144.5(5) 3_665 .
C1' C2' C3' O1' -34.7(6) . .
C1' C2' C3' C4' -35.4(7) 3_665 .
C1' C2' C3' C4' 145.4(5) . .
O1' C3' C4' C9' 159.5(5) . .
C2' C3' C4' C9' -20.7(7) . .
O1' C3' C4' C5' -15.6(7) . .
C2' C3' C4' C5' 164.2(5) . .
C9' C4' C5' C6' 1.6(8) . .
C3' C4' C5' C6' 176.9(5) . .
C4' C5' C6' C7' -0.5(8) . .
C5' C6' C7' O2' 178.9(5) . .
C5' C6' C7' C8' -0.5(8) . .
O2' C7' C8' C9' -179.1(5) . .
C6' C7' C8' C9' 0.2(8) . .
C7' C8' C9' C4' 0.9(8) . .
C5' C4' C9' C8' -1.8(8) . .
C3' C4' C9' C8' -176.9(5) . .
C3S O2S C2S O1S -6(3) . .
C3S O2S C2S C1S 178.9(15) . .
C2S O2S C3S C4S -173.9(14) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 92011712
