#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512791.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_4512791
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-120K
_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                112.504(13)
_cell_angle_beta                 117.532(13)
_cell_angle_gamma                95.440(9)
_cell_formula_units_Z            1
_cell_length_a                   10.0301(10)
_cell_length_b                   10.2569(12)
_cell_length_c                   10.8246(17)
_cell_measurement_reflns_used    1691
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.0725
_cell_measurement_theta_min      3.8348
_cell_volume                     860.7(3)
_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      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.848
_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  0.0564
_diffrn_reflns_av_unetI/netI     0.1032
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8162
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9629
_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            colorless
_exptl_crystal_density_diffrn    1.290
_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         0.453
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0645
_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)+(0.0616P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                2380
_reflns_number_total             3922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-oc-1D-combined.cif
_cod_data_source_block           1-oc-1d-120k
_cod_original_cell_volume        860.65(19)
_cod_database_code               4512791
#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 1.29831(17) 0.76008(19) 1.24587(17) 0.0256(4) Uani 1 1 d .
H1 H 1.2352 0.7766 1.2761 0.038 Uiso 1 1 calc GR
O2 O 0.62896(19) -0.16105(18) 0.44447(19) 0.0271(4) Uani 1 1 d .
H2 H 0.5296 -0.1843 0.3865 0.041 Uiso 1 1 calc GR
C2 C 0.9577(2) 0.4069(2) 0.5684(2) 0.0160(5) Uani 1 1 d .
C8 C 1.2956(3) 0.6258(3) 1.0123(3) 0.0233(6) Uani 1 1 d .
H8 H 1.4073 0.6475 1.0768 0.028 Uiso 1 1 calc R
C1 C 1.0660(2) 0.3801(2) 0.5016(3) 0.0172(5) Uani 1 1 d .
H1A H 1.1450 0.3400 0.5584 0.021 Uiso 1 1 calc R
H1B H 0.9997 0.3037 0.3877 0.021 Uiso 1 1 calc R
O3 O 0.6735(2) 0.7133(2) 0.6458(2) 0.0321(6) Uani 0.936(4) 1 d .
H3 H 0.6824 0.7708 0.6099 0.048 Uiso 0.936(4) 1 calc GR
C4 C 1.0523(2) 0.5091(2) 0.7494(2) 0.0162(5) Uani 1 1 d .
C5 C 0.9735(2) 0.5674(2) 0.8233(3) 0.0186(5) Uani 1 1 d .
H5 H 0.8625 0.5488 0.7591 0.022 Uiso 1 1 calc R
C6 C 1.0511(3) 0.6520(3) 0.9876(3) 0.0208(5) Uani 1 1 d .
H6 H 0.9938 0.6904 1.0345 0.025 Uiso 1 1 calc R
C10 C 0.8642(2) 0.2554(2) 0.5318(2) 0.0173(5) Uani 1 1 d .
C12 C 0.6189(3) 0.0499(3) 0.3942(3) 0.0219(5) Uani 1 1 d .
H12 H 0.5066 0.0068 0.3214 0.026 Uiso 1 1 calc R
C3 C 0.8459(3) 0.4787(2) 0.4820(3) 0.0183(5) Uani 1 1 d .
H3A H 0.7746 0.4046 0.3677 0.022 Uiso 1 1 calc R
H3B H 0.7783 0.5037 0.5254 0.022 Uiso 1 1 calc R
C15 C 0.9441(3) 0.1766(2) 0.6057(3) 0.0193(5) Uani 1 1 d .
H15 H 1.0563 0.2192 0.6790 0.023 Uiso 1 1 calc R
C14 C 0.8660(3) 0.0390(3) 0.5760(3) 0.0216(5) Uani 1 1 d .
H14 H 0.9242 -0.0114 0.6281 0.026 Uiso 1 1 calc R
C7 C 1.2131(3) 0.6797(2) 1.0821(2) 0.0180(5) Uani 1 1 d .
C9 C 1.2160(2) 0.5401(3) 0.8481(3) 0.0206(5) Uani 1 1 d .
H9 H 1.2738 0.5017 0.8018 0.025 Uiso 1 1 calc R
C13 C 0.7018(3) -0.0248(2) 0.4692(3) 0.0204(5) Uani 1 1 d .
C11 C 0.6985(3) 0.1875(3) 0.4247(3) 0.0201(5) Uani 1 1 d .
H11 H 0.6394 0.2370 0.3718 0.024 Uiso 1 1 calc R
C16 C 0.7007(3) 0.7947(3) 0.7938(3) 0.0239(6) Uani 0.936(4) 1 d .
C21 C 0.7778(3) 0.9463(3) 0.8828(3) 0.0296(7) Uani 0.936(4) 1 d .
H21 H 0.8138 0.9982 0.8418 0.036 Uiso 0.936(4) 1 calc R
C17 C 0.6472(3) 0.7123(3) 0.8504(3) 0.0249(6) Uani 0.936(4) 1 d .
C22 C 0.5647(3) 0.5491(3) 0.7520(3) 0.0307(7) Uani 0.936(4) 1 d .
H22A H 0.4986 0.5233 0.6398 0.046 Uiso 0.936(4) 1 calc GR
H22B H 0.4971 0.5180 0.7850 0.046 Uiso 0.936(4) 1 calc GR
H22C H 0.6438 0.4976 0.7658 0.046 Uiso 0.936(4) 1 calc GR
C18 C 0.6756(3) 0.7946(3) 1.0017(3) 0.0309(7) Uani 0.936(4) 1 d .
H18 H 0.6410 0.7431 1.0438 0.037 Uiso 0.936(4) 1 calc R
C19 C 0.7515(4) 0.9468(4) 1.0931(4) 0.0406(8) Uani 0.936(4) 1 d .
H19 H 0.7680 0.9981 1.1956 0.049 Uiso 0.936(4) 1 calc R
C20 C 0.8037(3) 1.0250(3) 1.0356(3) 0.0372(8) Uani 0.936(4) 1 d .
H20 H 0.8563 1.1301 1.0979 0.045 Uiso 0.936(4) 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 112.92(17) .
C4 C2 C10 107.66(17) .
C4 C2 C3 110.46(18) .
C10 C2 C1 108.47(17) .
C10 C2 C3 111.68(16) .
C3 C2 C1 105.69(18) .
C7 C8 H8 119.9 .
C7 C8 C9 120.3(2) .
C9 C8 H8 119.9 .
C2 C1 H1A 108.9 .
C2 C1 H1B 108.9 .
H1A C1 H1B 107.7 .
C3 C1 C2 113.26(18) 2_766
C3 C1 H1A 108.9 2_766
C3 C1 H1B 108.9 2_766
C16 O3 H3 109.5 .
C5 C4 C2 119.94(18) .
C5 C4 C9 116.9(2) .
C9 C4 C2 123.0(2) .
C4 C5 H5 118.8 .
C4 C5 C6 122.5(2) .
C6 C5 H5 118.8 .
C5 C6 H6 120.4 .
C7 C6 C5 119.1(2) .
C7 C6 H6 120.4 .
C15 C10 C2 120.14(18) .
C15 C10 C11 116.3(2) .
C11 C10 C2 123.5(2) .
C13 C12 H12 119.8 .
C13 C12 C11 120.4(2) .
C11 C12 H12 119.8 .
C2 C3 H3A 108.8 .
C2 C3 H3B 108.8 .
C1 C3 C2 113.59(17) 2_766
C1 C3 H3A 108.8 2_766
C1 C3 H3B 108.8 2_766
H3A C3 H3B 107.7 .
C10 C15 H15 118.7 .
C14 C15 C10 122.6(2) .
C14 C15 H15 118.7 .
C15 C14 H14 120.3 .
C15 C14 C13 119.4(2) .
C13 C14 H14 120.3 .
O1 C7 C8 117.34(19) .
O1 C7 C6 122.8(2) .
C8 C7 C6 119.8(2) .
C8 C9 C4 121.3(2) .
C8 C9 H9 119.3 .
C4 C9 H9 119.3 .
O2 C13 C12 122.94(19) .
O2 C13 C14 117.5(2) .
C12 C13 C14 119.6(2) .
C10 C11 H11 119.2 .
C12 C11 C10 121.6(2) .
C12 C11 H11 119.2 .
O3 C16 C21 122.1(2) .
O3 C16 C17 115.7(2) .
C21 C16 C17 122.2(3) .
C16 C21 H21 120.1 .
C16 C21 C20 119.8(3) .
C20 C21 H21 120.1 .
C16 C17 C22 121.0(2) .
C18 C17 C16 116.0(2) .
C18 C17 C22 123.1(2) .
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 118.4 .
C19 C18 C17 123.1(3) .
C19 C18 H18 118.4 .
C18 C19 H19 120.0 .
C18 C19 C20 119.9(3) .
C20 C19 H19 120.0 .
C21 C20 H20 120.5 .
C19 C20 C21 119.0(3) .
C19 C20 H20 120.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8400 .
O1 C7 1.378(3) .
O2 H2 0.8400 .
O2 C13 1.378(3) .
C2 C1 1.552(3) .
C2 C4 1.535(3) .
C2 C10 1.536(3) .
C2 C3 1.546(3) .
C8 H8 0.9500 .
C8 C7 1.381(3) .
C8 C9 1.389(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C3 1.525(3) 2_766
O3 H3 0.8400 .
O3 C16 1.366(3) .
C4 C5 1.389(3) .
C4 C9 1.399(3) .
C5 H5 0.9500 .
C5 C6 1.390(3) .
C6 H6 0.9500 .
C6 C7 1.386(3) .
C10 C15 1.400(3) .
C10 C11 1.405(3) .
C12 H12 0.9500 .
C12 C13 1.382(3) .
C12 C11 1.387(3) .
C3 C1 1.525(3) 2_766
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C15 H15 0.9500 .
C15 C14 1.386(3) .
C14 H14 0.9500 .
C14 C13 1.391(3) .
C9 H9 0.9500 .
C11 H11 0.9500 .
C16 C21 1.371(4) .
C16 C17 1.411(4) .
C21 H21 0.9500 .
C21 C20 1.412(4) .
C17 C22 1.477(4) .
C17 C18 1.393(4) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C18 H18 0.9500 .
C18 C19 1.375(4) .
C19 H19 0.9500 .
C19 C20 1.382(4) .
C20 H20 0.9500 .
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 175.5(2) .
C2 C4 C9 C8 -176.1(2) .
C2 C10 C15 C14 -179.4(2) .
C2 C10 C11 C12 179.5(2) .
C1 C2 C4 C5 167.53(19) .
C1 C2 C4 C9 -16.8(3) .
C1 C2 C10 C15 67.2(3) .
C1 C2 C10 C11 -112.3(2) .
C1 C2 C3 C1 -55.2(2) 2_766
O3 C16 C21 C20 -179.6(3) .
O3 C16 C17 C22 -1.1(3) .
O3 C16 C17 C18 179.5(2) .
C4 C2 C1 C3 -65.8(2) 2_766
C4 C2 C10 C15 -55.3(3) .
C4 C2 C10 C11 125.2(2) .
C4 C2 C3 C1 67.2(2) 2_766
C4 C5 C6 C7 0.0(3) .
C5 C4 C9 C8 -0.3(3) .
C5 C6 C7 O1 -178.8(2) .
C5 C6 C7 C8 1.3(3) .
C10 C2 C1 C3 174.92(17) 2_766
C10 C2 C4 C5 -72.8(2) .
C10 C2 C4 C9 102.9(2) .
C10 C2 C3 C1 -173.00(18) 2_766
C10 C15 C14 C13 -0.2(4) .
C3 C2 C1 C3 55.0(2) 2_766
C3 C2 C4 C5 49.4(3) .
C3 C2 C4 C9 -134.9(2) .
C3 C2 C10 C15 -176.7(2) .
C3 C2 C10 C11 3.8(3) .
C15 C10 C11 C12 0.0(3) .
C15 C14 C13 O2 -179.4(2) .
C15 C14 C13 C12 0.0(3) .
C7 C8 C9 C4 1.6(4) .
C9 C8 C7 O1 178.0(2) .
C9 C8 C7 C6 -2.0(3) .
C9 C4 C5 C6 -0.5(3) .
C13 C12 C11 C10 -0.2(4) .
C11 C10 C15 C14 0.1(3) .
C11 C12 C13 O2 179.5(2) .
C11 C12 C13 C14 0.1(4) .
C16 C21 C20 C19 0.5(4) .
C16 C17 C18 C19 -0.2(4) .
C21 C16 C17 C22 -179.9(2) .
C21 C16 C17 C18 0.8(4) .
C17 C16 C21 C20 -0.9(4) .
C17 C18 C19 C20 -0.2(4) .
C22 C17 C18 C19 -179.6(3) .
C18 C19 C20 C21 0.0(4) .
