#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512793.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_4512793
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-210K
_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                112.492(10)
_cell_angle_beta                 117.244(10)
_cell_angle_gamma                95.864(8)
_cell_formula_units_Z            1
_cell_length_a                   10.0464(9)
_cell_length_b                   10.3584(11)
_cell_length_c                   10.8328(12)
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.0680
_cell_measurement_theta_min      3.7568
_cell_volume                     871.7(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      210(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.851
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8204
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9634
_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    1.274
_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         0.404
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0562
_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)+(0.0576P)²+0.2438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                2656
_reflns_number_total             3983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-oc-1D-combined.cif
_cod_data_source_block           1-oc-1d-210k
_cod_original_cell_volume        871.65(16)
_cod_database_code               4512793
#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 1.30181(16) 0.75916(16) 1.24603(15) 0.0373(4) Uani 1 1 d .
H1 H 1.2401 0.7758 1.2765 0.056 Uiso 1 1 calc GR
O2 O 0.63216(17) -0.15784(16) 0.44529(18) 0.0396(4) Uani 1 1 d .
H2 H 0.5342 -0.1788 0.3926 0.059 Uiso 1 1 calc GR
C2 C 0.95843(19) 0.4076(2) 0.5684(2) 0.0217(4) Uani 1 1 d .
C8 C 1.2977(2) 0.6261(2) 1.0122(2) 0.0324(5) Uani 1 1 d .
H8 H 1.4079 0.6472 1.0756 0.039 Uiso 1 1 calc R
C1 C 1.0661(2) 0.3817(2) 0.5008(2) 0.0234(4) Uani 1 1 d .
H1A H 1.1444 0.3430 0.5566 0.028 Uiso 1 1 calc R
H1B H 1.0003 0.3064 0.3883 0.028 Uiso 1 1 calc R
O3 O 0.6746(2) 0.71488(19) 0.6456(2) 0.0505(6) Uani 0.923(4) 1 d .
H3 H 0.6836 0.7711 0.6100 0.076 Uiso 0.923(4) 1 calc GR
C4 C 1.0545(2) 0.5090(2) 0.7501(2) 0.0220(4) Uani 1 1 d .
C5 C 0.9761(2) 0.5674(2) 0.8251(2) 0.0265(4) Uani 1 1 d .
H5 H 0.8665 0.5494 0.7626 0.032 Uiso 1 1 calc R
C6 C 1.0552(2) 0.6512(2) 0.9891(2) 0.0286(4) Uani 1 1 d .
H6 H 0.9994 0.6886 1.0365 0.034 Uiso 1 1 calc R
C10 C 0.8656(2) 0.2563(2) 0.5324(2) 0.0233(4) Uani 1 1 d .
C12 C 0.6216(2) 0.0511(2) 0.3956(2) 0.0313(5) Uani 1 1 d .
H12 H 0.5108 0.0078 0.3235 0.038 Uiso 1 1 calc R
C3 C 0.8465(2) 0.4777(2) 0.4833(2) 0.0236(4) Uani 1 1 d .
H3A H 0.7757 0.4047 0.3704 0.028 Uiso 1 1 calc R
H3B H 0.7803 0.5016 0.5270 0.028 Uiso 1 1 calc R
C15 C 0.9465(2) 0.1797(2) 0.6068(2) 0.0286(4) Uani 1 1 d .
H15 H 1.0571 0.2227 0.6795 0.034 Uiso 1 1 calc R
C14 C 0.8686(2) 0.0425(2) 0.5765(2) 0.0316(5) Uani 1 1 d .
H14 H 0.9262 -0.0066 0.6275 0.038 Uiso 1 1 calc R
C7 C 1.2156(2) 0.6790(2) 1.0817(2) 0.0260(4) Uani 1 1 d .
C9 C 1.2171(2) 0.5410(2) 0.8478(2) 0.0296(4) Uani 1 1 d .
H9 H 1.2740 0.5042 0.8015 0.035 Uiso 1 1 calc R
C13 C 0.7053(2) -0.0219(2) 0.4706(2) 0.0287(4) Uani 1 1 d .
C11 C 0.7012(2) 0.1883(2) 0.4269(2) 0.0289(4) Uani 1 1 d .
H11 H 0.6428 0.2368 0.3755 0.035 Uiso 1 1 calc R
C16 C 0.7011(3) 0.7961(3) 0.7935(3) 0.0352(6) Uani 0.923(4) 1 d .
C21 C 0.7755(3) 0.9457(3) 0.8807(3) 0.0455(7) Uani 0.923(4) 1 d .
H21 H 0.8102 0.9971 0.8399 0.055 Uiso 0.923(4) 1 calc R
C17 C 0.6475(3) 0.7133(3) 0.8490(3) 0.0380(6) Uani 0.923(4) 1 d .
C22 C 0.5671(3) 0.5513(3) 0.7512(3) 0.0488(7) Uani 0.923(4) 1 d .
H22A H 0.4986 0.5258 0.6408 0.073 Uiso 0.923(4) 1 calc GR
H22B H 0.5038 0.5190 0.7865 0.073 Uiso 0.923(4) 1 calc GR
H22C H 0.6461 0.5025 0.7618 0.073 Uiso 0.923(4) 1 calc GR
C18 C 0.6754(3) 0.7937(3) 0.9998(3) 0.0499(7) Uani 0.923(4) 1 d .
H18 H 0.6421 0.7426 1.0416 0.060 Uiso 0.923(4) 1 calc R
C19 C 0.7498(4) 0.9451(4) 1.0903(4) 0.0673(9) Uani 0.923(4) 1 d .
H19 H 0.7660 0.9952 1.1916 0.081 Uiso 0.923(4) 1 calc R
C20 C 0.8007(4) 1.0236(3) 1.0332(3) 0.0604(8) Uani 0.923(4) 1 d .
H20 H 0.8512 1.1271 1.0945 0.073 Uiso 0.923(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 112.68(14) .
C4 C2 C10 107.35(14) .
C10 C2 C1 108.35(14) .
C3 C2 C1 105.97(14) .
C3 C2 C4 110.81(15) .
C3 C2 C10 111.72(14) .
C7 C8 H8 120.1 .
C7 C8 C9 119.74(17) .
C9 C8 H8 120.1 .
C2 C1 H1A 109.0 .
C2 C1 H1B 109.0 .
H1A C1 H1B 107.8 .
C3 C1 C2 113.13(14) 2_766
C3 C1 H1A 109.0 2_766
C3 C1 H1B 109.0 2_766
C16 O3 H3 109.5 .
C5 C4 C2 119.68(15) .
C9 C4 C2 123.54(16) .
C9 C4 C5 116.69(16) .
C4 C5 H5 119.0 .
C6 C5 C4 121.97(17) .
C6 C5 H5 119.0 .
C5 C6 H6 120.2 .
C7 C6 C5 119.57(17) .
C7 C6 H6 120.2 .
C15 C10 C2 119.98(16) .
C11 C10 C2 123.40(16) .
C11 C10 C15 116.61(17) .
C13 C12 H12 120.0 .
C13 C12 C11 119.92(18) .
C11 C12 H12 120.0 .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.50(14) 2_766
C1 C3 H3A 108.9 2_766
C1 C3 H3B 108.9 2_766
H3A C3 H3B 107.7 .
C10 C15 H15 119.0 .
C14 C15 C10 122.07(17) .
C14 C15 H15 119.0 .
C15 C14 H14 120.1 .
C13 C14 C15 119.74(18) .
C13 C14 H14 120.1 .
C8 C7 O1 116.92(16) .
C6 C7 O1 122.85(17) .
C6 C7 C8 120.24(17) .
C8 C9 H9 119.1 .
C4 C9 C8 121.77(17) .
C4 C9 H9 119.1 .
O2 C13 C12 122.44(17) .
O2 C13 C14 117.87(17) .
C12 C13 C14 119.70(18) .
C10 C11 H11 119.0 .
C12 C11 C10 121.96(18) .
C12 C11 H11 119.0 .
O3 C16 C17 115.2(2) .
C21 C16 O3 122.2(2) .
C21 C16 C17 122.6(2) .
C16 C21 H21 120.1 .
C16 C21 C20 119.7(2) .
C20 C21 H21 120.1 .
C16 C17 C22 121.1(2) .
C18 C17 C16 116.0(2) .
C18 C17 C22 122.9(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 118.7 .
C19 C18 C17 122.6(3) .
C19 C18 H18 118.7 .
C18 C19 H19 119.8 .
C20 C19 C18 120.3(3) .
C20 C19 H19 119.8 .
C21 C20 H20 120.6 .
C19 C20 C21 118.8(3) .
C19 C20 H20 120.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8300 .
O1 C7 1.385(2) .
O2 H2 0.8300 .
O2 C13 1.381(2) .
C2 C1 1.553(2) .
C2 C4 1.542(2) .
C2 C10 1.543(3) .
C2 C3 1.540(2) .
C8 H8 0.9400 .
C8 C7 1.376(3) .
C8 C9 1.392(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 C3 1.526(3) 2_766
O3 H3 0.8300 .
O3 C16 1.370(3) .
C4 C5 1.398(2) .
C4 C9 1.392(2) .
C5 H5 0.9400 .
C5 C6 1.389(3) .
C6 H6 0.9400 .
C6 C7 1.375(3) .
C10 C15 1.400(3) .
C10 C11 1.395(2) .
C12 H12 0.9400 .
C12 C13 1.383(3) .
C12 C11 1.388(3) .
C3 C1 1.526(3) 2_766
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C15 H15 0.9400 .
C15 C14 1.386(3) .
C14 H14 0.9400 .
C14 C13 1.385(3) .
C9 H9 0.9400 .
C11 H11 0.9400 .
C16 C21 1.360(3) .
C16 C17 1.409(3) .
C21 H21 0.9400 .
C21 C20 1.414(4) .
C17 C22 1.473(3) .
C17 C18 1.390(4) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 H22C 0.9700 .
C18 H18 0.9400 .
C18 C19 1.376(4) .
C19 H19 0.9400 .
C19 C20 1.376(4) .
C20 H20 0.9400 .
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 175.69(16) .
C2 C4 C9 C8 -176.18(17) .
C2 C10 C15 C14 -179.02(17) .
C2 C10 C11 C12 179.13(17) .
C1 C2 C4 C5 167.16(16) .
C1 C2 C4 C9 -16.3(2) .
C1 C2 C10 C15 67.4(2) .
C1 C2 C10 C11 -112.32(18) .
C1 C2 C3 C1 -55.3(2) 2_766
O3 C16 C21 C20 -179.6(2) .
O3 C16 C17 C22 -0.8(3) .
O3 C16 C17 C18 179.2(2) .
C4 C2 C1 C3 -66.31(19) 2_766
C4 C2 C10 C15 -54.6(2) .
C4 C2 C10 C11 125.72(18) .
C4 C2 C3 C1 67.28(18) 2_766
C4 C5 C6 C7 0.4(3) .
C5 C4 C9 C8 0.4(3) .
C5 C6 C7 O1 -178.71(17) .
C5 C6 C7 C8 0.9(3) .
C10 C2 C1 C3 175.06(14) 2_766
C10 C2 C4 C5 -73.6(2) .
C10 C2 C4 C9 102.90(19) .
C10 C2 C3 C1 -173.06(14) 2_766
C10 C15 C14 C13 -0.5(3) .
C3 C2 C1 C3 55.0(2) 2_766
C3 C2 C4 C5 48.6(2) .
C3 C2 C4 C9 -134.86(18) .
C3 C2 C10 C15 -176.28(16) .
C3 C2 C10 C11 4.0(2) .
C15 C10 C11 C12 -0.6(3) .
C15 C14 C13 O2 -179.24(17) .
C15 C14 C13 C12 0.2(3) .
C7 C8 C9 C4 0.8(3) .
C9 C8 C7 O1 178.12(17) .
C9 C8 C7 C6 -1.5(3) .
C9 C4 C5 C6 -1.1(3) .
C13 C12 C11 C10 0.3(3) .
C11 C10 C15 C14 0.7(3) .
C11 C12 C13 O2 179.33(18) .
C11 C12 C13 C14 -0.1(3) .
C16 C21 C20 C19 0.5(4) .
C16 C17 C18 C19 0.4(4) .
C21 C16 C17 C22 179.9(2) .
C21 C16 C17 C18 -0.1(3) .
C17 C16 C21 C20 -0.3(4) .
C17 C18 C19 C20 -0.2(5) .
C22 C17 C18 C19 -179.6(2) .
C18 C19 C20 C21 -0.3(5) .
