#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512792.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_4512792
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-165K
_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                112.454(9)
_cell_angle_beta                 117.403(9)
_cell_angle_gamma                95.683(7)
_cell_formula_units_Z            1
_cell_length_a                   10.0433(8)
_cell_length_b                   10.3060(10)
_cell_length_c                   10.8398(11)
_cell_measurement_reflns_used    2303
_cell_measurement_temperature    165(2)
_cell_measurement_theta_max      29.2205
_cell_measurement_theta_min      3.7661
_cell_volume                     867.4(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      165(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8212
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.9632
_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    1.280
_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         0.370
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0533
_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)+(0.0545P)²+0.2267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                2835
_reflns_number_total             3982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-oc-1D-combined.cif
_cod_data_source_block           1-oc-1d-165k
_cod_original_cell_volume        867.40(14)
_cod_database_code               4512792
#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 1.30008(14) 0.75970(14) 1.24606(13) 0.0296(3) Uani 1 1 d .
H1 H 1.2376 0.7792 1.2762 0.044 Uiso 1 1 calc GR
O2 O 0.63060(15) -0.15946(14) 0.44510(15) 0.0314(3) Uani 1 1 d .
H2 H 0.5314 -0.1808 0.3912 0.047 Uiso 1 1 calc GR
C2 C 0.95799(18) 0.40692(18) 0.56804(18) 0.0177(3) Uani 1 1 d .
C8 C 1.2966(2) 0.6259(2) 1.0122(2) 0.0267(4) Uani 1 1 d .
H8 H 1.4080 0.6471 1.0764 0.032 Uiso 1 1 calc R
C1 C 1.06586(19) 0.38095(18) 0.50116(19) 0.0190(3) Uani 1 1 d .
H1A H 1.1448 0.3412 0.5576 0.023 Uiso 1 1 calc R
H1B H 0.9996 0.3049 0.3875 0.023 Uiso 1 1 calc R
O3 O 0.6743(2) 0.71396(16) 0.64567(17) 0.0392(4) Uani 0.934(3) 1 d .
H3 H 0.6831 0.7714 0.6098 0.059 Uiso 0.934(3) 1 calc GR
C4 C 1.05369(18) 0.50904(17) 0.74981(18) 0.0179(3) Uani 1 1 d .
C5 C 0.97459(19) 0.56768(18) 0.82416(19) 0.0216(4) Uani 1 1 d .
H5 H 0.8638 0.5497 0.7605 0.026 Uiso 1 1 calc R
C6 C 1.0530(2) 0.65144(19) 0.9882(2) 0.0236(4) Uani 1 1 d .
H6 H 0.9963 0.6893 1.0356 0.028 Uiso 1 1 calc R
C10 C 0.86470(18) 0.25576(18) 0.53214(18) 0.0189(3) Uani 1 1 d .
C12 C 0.6203(2) 0.0504(2) 0.3949(2) 0.0251(4) Uani 1 1 d .
H12 H 0.5083 0.0070 0.3219 0.030 Uiso 1 1 calc R
C3 C 0.84590(19) 0.47770(18) 0.48231(19) 0.0191(3) Uani 1 1 d .
H3A H 0.7746 0.4039 0.3682 0.023 Uiso 1 1 calc R
H3B H 0.7786 0.5021 0.5259 0.023 Uiso 1 1 calc R
C15 C 0.94539(19) 0.17834(19) 0.6065(2) 0.0226(4) Uani 1 1 d .
H15 H 1.0573 0.2216 0.6801 0.027 Uiso 1 1 calc R
C14 C 0.8675(2) 0.04065(19) 0.5764(2) 0.0248(4) Uani 1 1 d .
H14 H 0.9258 -0.0093 0.6283 0.030 Uiso 1 1 calc R
C7 C 1.21434(19) 0.67922(18) 1.08172(19) 0.0213(4) Uani 1 1 d .
C9 C 1.2164(2) 0.5410(2) 0.8480(2) 0.0246(4) Uani 1 1 d .
H9 H 1.2742 0.5038 0.8016 0.030 Uiso 1 1 calc R
C13 C 0.7036(2) -0.02374(18) 0.4698(2) 0.0230(4) Uani 1 1 d .
C11 C 0.70006(19) 0.18775(19) 0.4261(2) 0.0228(4) Uani 1 1 d .
H11 H 0.6410 0.2372 0.3739 0.027 Uiso 1 1 calc R
C16 C 0.7015(2) 0.7954(2) 0.7943(2) 0.0273(5) Uani 0.934(3) 1 d .
C21 C 0.7771(3) 0.9463(2) 0.8825(3) 0.0355(5) Uani 0.934(3) 1 d .
H21 H 0.8125 0.9985 0.8415 0.043 Uiso 0.934(3) 1 calc R
C17 C 0.6472(2) 0.7133(2) 0.8500(2) 0.0292(5) Uani 0.934(3) 1 d .
C22 C 0.5658(2) 0.5498(2) 0.7510(3) 0.0377(6) Uani 0.934(3) 1 d .
H22A H 0.4973 0.5244 0.6395 0.056 Uiso 0.934(3) 1 calc GR
H22B H 0.5008 0.5171 0.7857 0.056 Uiso 0.934(3) 1 calc GR
H22C H 0.6454 0.4997 0.7624 0.056 Uiso 0.934(3) 1 calc GR
C18 C 0.6752(3) 0.7942(3) 1.0011(3) 0.0392(6) Uani 0.934(3) 1 d .
H18 H 0.6413 0.7425 1.0432 0.047 Uiso 0.934(3) 1 calc R
C19 C 0.7500(3) 0.9458(3) 1.0915(3) 0.0515(7) Uani 0.934(3) 1 d .
H19 H 0.7657 0.9969 1.1935 0.062 Uiso 0.934(3) 1 calc R
C20 C 0.8022(3) 1.0242(3) 1.0345(3) 0.0465(6) Uani 0.934(3) 1 d .
H20 H 0.8542 1.1290 1.0967 0.056 Uiso 0.934(3) 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 112.73(13) .
C10 C2 C1 108.66(13) .
C10 C2 C4 107.38(12) .
C10 C2 C3 111.57(12) .
C3 C2 C1 105.89(12) .
C3 C2 C4 110.66(13) .
C7 C8 H8 120.0 .
C7 C8 C9 119.96(15) .
C9 C8 H8 120.0 .
C2 C1 H1A 108.9 .
C2 C1 H1B 108.9 .
H1A C1 H1B 107.7 .
C3 C1 C2 113.24(13) 2_766
C3 C1 H1A 108.9 2_766
C3 C1 H1B 108.9 2_766
C16 O3 H3 109.5 .
C5 C4 C2 119.70(14) .
C9 C4 C2 123.42(14) .
C9 C4 C5 116.79(15) .
C4 C5 H5 119.0 .
C6 C5 C4 122.02(15) .
C6 C5 H5 119.0 .
C5 C6 H6 120.3 .
C7 C6 C5 119.44(16) .
C7 C6 H6 120.3 .
C15 C10 C2 119.91(14) .
C11 C10 C2 123.55(14) .
C11 C10 C15 116.53(15) .
C13 C12 H12 119.9 .
C13 C12 C11 120.15(16) .
C11 C12 H12 119.9 .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.37(13) 2_766
C1 C3 H3A 108.9 2_766
C1 C3 H3B 108.9 2_766
H3A C3 H3B 107.7 .
C10 C15 H15 118.9 .
C14 C15 C10 122.25(15) .
C14 C15 H15 118.9 .
C15 C14 H14 120.2 .
C15 C14 C13 119.59(15) .
C13 C14 H14 120.2 .
C8 C7 O1 117.23(15) .
C8 C7 C6 120.04(15) .
C6 C7 O1 122.72(15) .
C8 C9 C4 121.73(16) .
C8 C9 H9 119.1 .
C4 C9 H9 119.1 .
O2 C13 C12 122.74(15) .
O2 C13 C14 117.74(15) .
C12 C13 C14 119.51(16) .
C10 C11 H11 119.0 .
C12 C11 C10 121.96(16) .
C12 C11 H11 119.0 .
O3 C16 C17 115.66(18) .
C21 C16 O3 122.15(18) .
C21 C16 C17 122.19(19) .
C16 C21 H21 120.1 .
C16 C21 C20 119.8(2) .
C20 C21 H21 120.1 .
C16 C17 C22 120.66(19) .
C18 C17 C16 116.27(19) .
C18 C17 C22 123.07(19) .
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 118.7 .
C19 C18 C17 122.6(2) .
C19 C18 H18 118.7 .
C18 C19 H19 119.9 .
C18 C19 C20 120.2(2) .
C20 C19 H19 119.9 .
C21 C20 H20 120.5 .
C19 C20 C21 119.0(2) .
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 1.3859(19) .
O2 H2 0.8400 .
O2 C13 1.377(2) .
C2 C1 1.550(2) .
C2 C4 1.545(2) .
C2 C10 1.539(2) .
C2 C3 1.543(2) .
C8 H8 0.9500 .
C8 C7 1.378(2) .
C8 C9 1.391(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C3 1.529(2) 2_766
O3 H3 0.8400 .
O3 C16 1.375(2) .
C4 C5 1.399(2) .
C4 C9 1.392(2) .
C5 H5 0.9500 .
C5 C6 1.390(2) .
C6 H6 0.9500 .
C6 C7 1.382(2) .
C10 C15 1.400(2) .
C10 C11 1.397(2) .
C12 H12 0.9500 .
C12 C13 1.385(2) .
C12 C11 1.386(2) .
C3 C1 1.529(2) 2_766
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C15 H15 0.9500 .
C15 C14 1.387(2) .
C14 H14 0.9500 .
C14 C13 1.390(2) .
C9 H9 0.9500 .
C11 H11 0.9500 .
C16 C21 1.368(3) .
C16 C17 1.407(3) .
C21 H21 0.9500 .
C21 C20 1.411(3) .
C17 C22 1.482(3) .
C17 C18 1.394(3) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C18 H18 0.9500 .
C18 C19 1.374(3) .
C19 H19 0.9500 .
C19 C20 1.380(3) .
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 175.39(15) .
C2 C4 C9 C8 -175.91(16) .
C2 C10 C15 C14 -178.90(15) .
C2 C10 C11 C12 178.99(15) .
C1 C2 C4 C5 167.16(14) .
C1 C2 C4 C9 -16.5(2) .
C1 C2 C10 C15 67.20(18) .
C1 C2 C10 C11 -112.21(17) .
C1 C2 C3 C1 -55.26(18) 2_766
O3 C16 C21 C20 -179.84(19) .
O3 C16 C17 C22 -0.2(3) .
O3 C16 C17 C18 179.45(17) .
C4 C2 C1 C3 -65.95(17) 2_766
C4 C2 C10 C15 -55.01(19) .
C4 C2 C10 C11 125.58(16) .
C4 C2 C3 C1 67.20(17) 2_766
C4 C5 C6 C7 0.5(3) .
C5 C4 C9 C8 0.6(2) .
C5 C6 C7 O1 -178.93(15) .
C5 C6 C7 C8 0.9(2) .
C10 C2 C1 C3 175.14(12) 2_766
C10 C2 C4 C5 -73.20(18) .
C10 C2 C4 C9 103.19(17) .
C10 C2 C3 C1 -173.30(13) 2_766
C10 C15 C14 C13 -0.4(3) .
C3 C2 C1 C3 55.17(18) 2_766
C3 C2 C4 C5 48.79(19) .
C3 C2 C4 C9 -134.83(16) .
C3 C2 C10 C15 -176.43(14) .
C3 C2 C10 C11 4.2(2) .
C15 C10 C11 C12 -0.4(2) .
C15 C14 C13 O2 -179.07(15) .
C15 C14 C13 C12 0.1(3) .
C7 C8 C9 C4 0.8(3) .
C9 C8 C7 O1 178.30(15) .
C9 C8 C7 C6 -1.6(3) .
C9 C4 C5 C6 -1.2(2) .
C13 C12 C11 C10 0.2(3) .
C11 C10 C15 C14 0.5(2) .
C11 C12 C13 O2 179.13(16) .
C11 C12 C13 C14 0.0(3) .
C16 C21 C20 C19 0.1(3) .
C16 C17 C18 C19 0.7(3) .
C21 C16 C17 C22 179.98(18) .
C21 C16 C17 C18 -0.3(3) .
C17 C16 C21 C20 -0.1(3) .
C17 C18 C19 C20 -0.7(4) .
C22 C17 C18 C19 -179.6(2) .
C18 C19 C20 C21 0.2(4) .
