#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512795.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_4512795
loop_
_publ_author_name
'Saraswatula, Viswanadha G.'
'Saha, Binoy K.'
_publ_section_title
;
 Modulation of Thermal Expansion by Guests and Polymorphism in a Hydrogen
 Bonded Host
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              593
_journal_paper_doi               10.1021/cg501178f
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C30 H28 O4, 2(C7 H8 O)'
_chemical_formula_sum            'C44 H44 O6'
_chemical_formula_weight         668.79
_chemical_name_common            1-oc-1D-298K
_chemical_name_systematic
;
 1,1,4,4-tetrakis(4-hydroxyphenyl)cyclohexane, 2-methylphenol 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                112.488(10)
_cell_angle_beta                 116.969(9)
_cell_angle_gamma                96.574(8)
_cell_formula_units_Z            1
_cell_length_a                   10.0400(8)
_cell_length_b                   10.4946(11)
_cell_length_c                   10.8190(10)
_cell_measurement_reflns_used    1968
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1265
_cell_measurement_theta_min      4.0233
_cell_volume                     879.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.846
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8416
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         4.03
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0852
_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)+(0.1513P)²+0.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2412
_refine_ls_wR_factor_ref         0.2794
_reflns_number_gt                2552
_reflns_number_total             4022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-oc-1D-combined.cif
_cod_data_source_block           1-oc-1d-298k
_cod_original_cell_volume        879.47(15)
_cod_database_code               4512795
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O3)=Sof(H3)=Sof(C16)=Sof(C21)=Sof(H21)=Sof(C17)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=
 FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C12(H12), C15(H15), C14(H14), C9(H9), C11(H11),
 C21(H21), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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_posn
O1 O 1.3047(2) 0.7566(2) 1.2469(2) 0.0555(6) Uani 1 1 d .
H1 H 1.2437 0.7709 1.2773 0.083 Uiso 1 1 calc GR
O2 O 0.6370(3) -0.1545(2) 0.4461(3) 0.0599(7) Uani 1 1 d .
H2 H 0.5401 -0.1795 0.3879 0.090 Uiso 1 1 calc GR
C2 C 0.9596(3) 0.4077(3) 0.5688(3) 0.0317(6) Uani 1 1 d .
C8 C 1.3001(3) 0.6267(3) 1.0127(3) 0.0475(7) Uani 1 1 d .
H8 H 1.4093 0.6482 1.0754 0.057 Uiso 1 1 calc R
C1 C 1.0668(3) 0.3848(3) 0.5005(3) 0.0343(6) Uani 1 1 d .
H1A H 1.1449 0.3478 0.5552 0.041 Uiso 1 1 calc R
H1B H 1.0013 0.3108 0.3887 0.041 Uiso 1 1 calc R
O3 O 0.6722(5) 0.7151(4) 0.6445(4) 0.0819(13) Uani 0.798(7) 1 d .
H3 H 0.6845 0.7684 0.6085 0.123 Uiso 0.798(7) 1 calc GR
C4 C 1.0568(3) 0.5093(3) 0.7510(3) 0.0320(6) Uani 1 1 d .
C5 C 0.9787(3) 0.5654(3) 0.8255(3) 0.0396(6) Uani 1 1 d .
H5 H 0.8699 0.5463 0.7636 0.048 Uiso 1 1 calc R
C6 C 1.0585(3) 0.6495(3) 0.9904(3) 0.0439(7) Uani 1 1 d .
H6 H 1.0036 0.6859 1.0375 0.053 Uiso 1 1 calc R
C10 C 0.8677(3) 0.2573(3) 0.5330(3) 0.0343(6) Uani 1 1 d .
C12 C 0.6250(3) 0.0506(3) 0.3959(3) 0.0484(7) Uani 1 1 d .
H12 H 0.5152 0.0058 0.3238 0.058 Uiso 1 1 calc R
C3 C 0.8465(3) 0.4753(3) 0.4830(3) 0.0352(6) Uani 1 1 d .
H3A H 0.7767 0.4032 0.3709 0.042 Uiso 1 1 calc R
H3B H 0.7803 0.4970 0.5258 0.042 Uiso 1 1 calc R
C15 C 0.9486(3) 0.1841(3) 0.6069(3) 0.0430(7) Uani 1 1 d .
H15 H 1.0583 0.2283 0.6793 0.052 Uiso 1 1 calc R
C14 C 0.8722(3) 0.0473(3) 0.5769(4) 0.0470(7) Uani 1 1 d .
H14 H 0.9304 0.0006 0.6277 0.056 Uiso 1 1 calc R
C7 C 1.2181(3) 0.6780(3) 1.0822(3) 0.0390(6) Uani 1 1 d .
C9 C 1.2190(3) 0.5425(3) 0.8479(3) 0.0445(7) Uani 1 1 d .
H9 H 1.2752 0.5076 0.8017 0.053 Uiso 1 1 calc R
C13 C 0.7101(3) -0.0187(3) 0.4717(3) 0.0436(7) Uani 1 1 d .
C11 C 0.7039(3) 0.1884(3) 0.4274(3) 0.0438(7) Uani 1 1 d .
H11 H 0.6453 0.2349 0.3765 0.053 Uiso 1 1 calc R
C16 C 0.7004(5) 0.8003(6) 0.7939(5) 0.0584(12) Uani 0.798(7) 1 d .
C21 C 0.7697(6) 0.9420(6) 0.8733(7) 0.0773(15) Uani 0.798(7) 1 d .
H21 H 0.8014 0.9907 0.8298 0.093 Uiso 0.798(7) 1 calc R
C17 C 0.6467(5) 0.7129(6) 0.8462(6) 0.0668(13) Uani 0.798(7) 1 d .
C22 C 0.5729(6) 0.5610(6) 0.7563(7) 0.0795(16) Uani 0.798(7) 1 d .
H22A H 0.5426 0.5293 0.6485 0.119 Uiso 0.798(7) 1 calc GR
H22B H 0.4796 0.5330 0.7582 0.119 Uiso 0.798(7) 1 calc GR
H22C H 0.6454 0.5156 0.8002 0.119 Uiso 0.798(7) 1 calc GR
C18 C 0.6761(6) 0.7959(6) 0.9998(6) 0.0715(14) Uani 0.798(7) 1 d .
H18 H 0.6445 0.7470 1.0432 0.086 Uiso 0.798(7) 1 calc R
C19 C 0.7492(9) 0.9454(9) 1.0869(8) 0.112(2) Uani 0.798(7) 1 d .
H19 H 0.7660 0.9937 1.1876 0.134 Uiso 0.798(7) 1 calc R
C20 C 0.7982(9) 1.0264(8) 1.0343(8) 0.101(2) Uani 0.798(7) 1 d .
H20 H 0.8466 1.1283 1.0947 0.122 Uiso 0.798(7) 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
C7 O1 H1 109.5 .
C13 O2 H2 109.5 .
C4 C2 C1 112.56(19) .
C4 C2 C3 110.9(2) .
C10 C2 C1 108.55(19) .
C10 C2 C4 107.49(19) .
C10 C2 C3 111.90(19) .
C3 C2 C1 105.44(19) .
C7 C8 H8 120.2 .
C7 C8 C9 119.7(2) .
C9 C8 H8 120.2 .
C2 C1 H1A 108.9 .
C2 C1 H1B 108.9 .
H1A C1 H1B 107.7 .
C3 C1 C2 113.2(2) 2_766
C3 C1 H1A 108.9 2_766
C3 C1 H1B 108.9 2_766
C16 O3 H3 109.5 .
C5 C4 C2 119.4(2) .
C9 C4 C2 123.5(2) .
C9 C4 C5 117.0(2) .
C4 C5 H5 119.1 .
C4 C5 C6 121.9(2) .
C6 C5 H5 119.1 .
C5 C6 H6 120.2 .
C7 C6 C5 119.5(2) .
C7 C6 H6 120.2 .
C15 C10 C2 120.1(2) .
C15 C10 C11 116.9(3) .
C11 C10 C2 123.1(2) .
C13 C12 H12 120.1 .
C13 C12 C11 119.9(3) .
C11 C12 H12 120.1 .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.6(2) 2_766
C1 C3 H3A 108.9 2_766
C1 C3 H3B 108.9 2_766
H3A C3 H3B 107.7 .
C10 C15 H15 118.8 .
C10 C15 C14 122.4(3) .
C14 C15 H15 118.8 .
C15 C14 H14 120.2 .
C13 C14 C15 119.6(3) .
C13 C14 H14 120.2 .
C8 C7 O1 116.7(2) .
C6 C7 O1 122.9(2) .
C6 C7 C8 120.3(2) .
C8 C9 H9 119.2 .
C4 C9 C8 121.6(2) .
C4 C9 H9 119.2 .
C12 C13 O2 122.0(3) .
C14 C13 O2 118.1(3) .
C14 C13 C12 119.8(3) .
C10 C11 C12 121.4(3) .
C10 C11 H11 119.3 .
C12 C11 H11 119.3 .
O3 C16 C17 111.6(4) .
C21 C16 O3 122.5(4) .
C21 C16 C17 125.9(5) .
C16 C21 H21 120.2 .
C16 C21 C20 119.6(5) .
C20 C21 H21 120.2 .
C22 C17 C16 123.7(5) .
C22 C17 C18 123.0(5) .
C18 C17 C16 113.3(5) .
C17 C22 H22A 109.5 .
C17 C22 H22B 109.5 .
C17 C22 H22C 109.5 .
H22A C22 H22B 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C17 C18 H18 118.8 .
C19 C18 C17 122.3(5) .
C19 C18 H18 118.8 .
C18 C19 H19 118.3 .
C20 C19 C18 123.4(6) .
C20 C19 H19 118.3 .
C21 C20 H20 122.2 .
C19 C20 C21 115.5(6) .
C19 C20 H20 122.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8200 .
O1 C7 1.384(3) .
O2 H2 0.8200 .
O2 C13 1.385(3) .
C2 C1 1.552(3) .
C2 C4 1.544(3) .
C2 C10 1.538(3) .
C2 C3 1.544(3) .
C8 H8 0.9300 .
C8 C7 1.375(4) .
C8 C9 1.391(4) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C3 1.520(4) 2_766
O3 H3 0.8200 .
O3 C16 1.383(6) .
C4 C5 1.389(3) .
C4 C9 1.384(4) .
C5 H5 0.9300 .
C5 C6 1.393(4) .
C6 H6 0.9300 .
C6 C7 1.364(4) .
C10 C15 1.383(4) .
C10 C11 1.388(4) .
C12 H12 0.9300 .
C12 C13 1.377(4) .
C12 C11 1.396(4) .
C3 C1 1.520(4) 2_766
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C15 H15 0.9300 .
C15 C14 1.386(4) .
C14 H14 0.9300 .
C14 C13 1.372(4) .
C9 H9 0.9300 .
C11 H11 0.9300 .
C16 C21 1.295(6) .
C16 C17 1.418(6) .
C21 H21 0.9300 .
C21 C20 1.487(8) .
C17 C22 1.388(7) .
C17 C18 1.414(7) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C18 H18 0.9300 .
C18 C19 1.366(9) .
C19 H19 0.9300 .
C19 C20 1.348(10) .
C20 H20 0.9300 .
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_4
C2 C4 C5 C6 175.6(2) .
C2 C4 C9 C8 -175.7(3) .
C2 C10 C15 C14 -178.8(2) .
C2 C10 C11 C12 178.9(2) .
C1 C2 C4 C5 166.6(2) .
C1 C2 C4 C9 -17.1(4) .
C1 C2 C10 C15 67.8(3) .
C1 C2 C10 C11 -111.9(3) .
C1 C2 C3 C1 -55.5(3) 2_766
O3 C16 C21 C20 -179.2(5) .
O3 C16 C17 C22 -0.9(6) .
O3 C16 C17 C18 178.9(4) .
C4 C2 C1 C3 -65.8(3) 2_766
C4 C2 C10 C15 -54.2(3) .
C4 C2 C10 C11 126.1(3) .
C4 C2 C3 C1 66.7(2) 2_766
C4 C5 C6 C7 -0.1(4) .
C5 C4 C9 C8 0.7(4) .
C5 C6 C7 O1 -177.9(3) .
C5 C6 C7 C8 1.3(4) .
C10 C2 C1 C3 175.3(2) 2_766
C10 C2 C4 C5 -73.9(3) .
C10 C2 C4 C9 102.4(3) .
C10 C2 C3 C1 -173.27(19) 2_766
C10 C15 C14 C13 -0.8(4) .
C3 C2 C1 C3 55.3(3) 2_766
C3 C2 C4 C5 48.7(3) .
C3 C2 C4 C9 -135.0(3) .
C3 C2 C10 C15 -176.3(2) .
C3 C2 C10 C11 4.0(3) .
C15 C10 C11 C12 -0.8(4) .
C15 C14 C13 O2 -179.1(2) .
C15 C14 C13 C12 0.6(4) .
C7 C8 C9 C4 0.5(5) .
C9 C8 C7 O1 177.8(3) .
C9 C8 C7 C6 -1.5(5) .
C9 C4 C5 C6 -0.9(4) .
C13 C12 C11 C10 0.7(4) .
C11 C10 C15 C14 0.9(4) .
C11 C12 C13 O2 179.1(3) .
C11 C12 C13 C14 -0.6(4) .
C16 C21 C20 C19 0.6(9) .
C16 C17 C18 C19 0.0(7) .
C21 C16 C17 C22 180.0(5) .
C21 C16 C17 C18 -0.2(6) .
C17 C16 C21 C20 -0.1(8) .
C17 C18 C19 C20 0.5(11) .
C22 C17 C18 C19 179.9(5) .
C18 C19 C20 C21 -0.8(11) .
