#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512794.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_4512794
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-255K
_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                112.518(7)
_cell_angle_beta                 117.072(7)
_cell_angle_gamma                96.240(5)
_cell_formula_units_Z            1
_cell_length_a                   10.0444(6)
_cell_length_b                   10.4376(8)
_cell_length_c                   10.8259(8)
_cell_measurement_reflns_used    2464
_cell_measurement_temperature    255(2)
_cell_measurement_theta_max      29.1242
_cell_measurement_theta_min      3.8277
_cell_volume                     876.59(16)
_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 0.993
_diffrn_measured_fraction_theta_max 0.850
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8342
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9636
_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    1.267
_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         0.775
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0680
_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)+(0.1186P)²+0.2183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1916
_refine_ls_wR_factor_ref         0.2152
_reflns_number_gt                2725
_reflns_number_total             4024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-oc-1D-combined.cif
_cod_data_source_block           1-oc-1d-255k
_cod_original_cell_volume        876.58(10)
_cod_database_code               4512794
#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 1.30323(18) 0.75785(19) 1.24639(17) 0.0459(5) Uani 1 1 d .
H1 H 1.2419 0.7769 1.2768 0.069 Uiso 1 1 calc GR
O2 O 0.6349(2) -0.15665(18) 0.4457(2) 0.0493(5) Uani 1 1 d .
H2 H 0.5368 -0.1809 0.3884 0.074 Uiso 1 1 calc GR
C2 C 0.9591(2) 0.4078(2) 0.5686(2) 0.0264(4) Uani 1 1 d .
C8 C 1.2989(2) 0.6265(3) 1.0123(2) 0.0394(5) Uani 1 1 d .
H8 H 1.4091 0.6479 1.0755 0.047 Uiso 1 1 calc R
C1 C 1.0667(2) 0.3834(2) 0.5009(2) 0.0279(4) Uani 1 1 d .
H1A H 1.1454 0.3457 0.5567 0.033 Uiso 1 1 calc R
H1B H 1.0009 0.3082 0.3882 0.033 Uiso 1 1 calc R
O3 O 0.6739(3) 0.7151(2) 0.6450(3) 0.0621(8) Uani 0.838(5) 1 d .
H3 H 0.6835 0.7702 0.6088 0.093 Uiso 0.838(5) 1 calc GR
C4 C 1.0558(2) 0.5091(2) 0.7505(2) 0.0265(4) Uani 1 1 d .
C5 C 0.9772(2) 0.5662(2) 0.8253(2) 0.0326(5) Uani 1 1 d .
H5 H 0.8675 0.5474 0.7627 0.039 Uiso 1 1 calc R
C6 C 1.0565(3) 0.6500(2) 0.9893(2) 0.0363(5) Uani 1 1 d .
H6 H 1.0008 0.6870 1.0368 0.044 Uiso 1 1 calc R
C10 C 0.8665(2) 0.2568(2) 0.5327(2) 0.0284(4) Uani 1 1 d .
C12 C 0.6229(3) 0.0506(2) 0.3957(3) 0.0389(5) Uani 1 1 d .
H12 H 0.5120 0.0063 0.3235 0.047 Uiso 1 1 calc R
C3 C 0.8462(2) 0.4760(2) 0.4830(2) 0.0288(4) Uani 1 1 d .
H3A H 0.7757 0.4030 0.3699 0.035 Uiso 1 1 calc R
H3B H 0.7797 0.4988 0.5265 0.035 Uiso 1 1 calc R
C15 C 0.9475(2) 0.1819(2) 0.6071(3) 0.0359(5) Uani 1 1 d .
H15 H 1.0583 0.2259 0.6801 0.043 Uiso 1 1 calc R
C14 C 0.8705(3) 0.0449(2) 0.5771(3) 0.0384(5) Uani 1 1 d .
H14 H 0.9287 -0.0030 0.6286 0.046 Uiso 1 1 calc R
C7 C 1.2169(2) 0.6785(2) 1.0820(2) 0.0322(5) Uani 1 1 d .
C9 C 1.2180(2) 0.5419(3) 0.8477(2) 0.0369(5) Uani 1 1 d .
H9 H 1.2749 0.5061 0.8012 0.044 Uiso 1 1 calc R
C13 C 0.7078(3) -0.0204(2) 0.4709(3) 0.0364(5) Uani 1 1 d .
C11 C 0.7024(2) 0.1882(2) 0.4271(2) 0.0361(5) Uani 1 1 d .
H11 H 0.6436 0.2359 0.3756 0.043 Uiso 1 1 calc R
C16 C 0.7010(3) 0.7980(4) 0.7939(4) 0.0442(7) Uani 0.838(5) 1 d .
C21 C 0.7730(4) 0.9439(4) 0.8775(4) 0.0591(9) Uani 0.838(5) 1 d .
H21 H 0.8060 0.9942 0.8350 0.071 Uiso 0.838(5) 1 calc R
C17 C 0.6473(3) 0.7134(4) 0.8480(4) 0.0500(8) Uani 0.838(5) 1 d .
C22 C 0.5703(4) 0.5558(4) 0.7541(5) 0.0614(10) Uani 0.838(5) 1 d .
H22A H 0.5132 0.5275 0.6421 0.092 Uiso 0.838(5) 1 calc GR
H22B H 0.4959 0.5251 0.7796 0.092 Uiso 0.838(5) 1 calc GR
H22C H 0.6497 0.5085 0.7770 0.092 Uiso 0.838(5) 1 calc GR
C18 C 0.6762(4) 0.7958(4) 1.0002(4) 0.0598(9) Uani 0.838(5) 1 d .
H18 H 0.6440 0.7459 1.0434 0.072 Uiso 0.838(5) 1 calc R
C19 C 0.7493(6) 0.9458(6) 1.0884(5) 0.0871(14) Uani 0.838(5) 1 d .
H19 H 0.7647 0.9956 1.1895 0.105 Uiso 0.838(5) 1 calc R
C20 C 0.8001(5) 1.0248(5) 1.0338(5) 0.0772(12) Uani 0.838(5) 1 d .
H20 H 0.8508 1.1278 1.0953 0.093 Uiso 0.838(5) 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 112.51(15) .
C4 C2 C10 107.36(15) .
C10 C2 C1 108.44(15) .
C3 C2 C1 105.87(15) .
C3 C2 C4 111.05(15) .
C3 C2 C10 111.64(15) .
C7 C8 H8 120.1 .
C7 C8 C9 119.75(19) .
C9 C8 H8 120.1 .
C2 C1 H1A 109.0 .
C2 C1 H1B 109.0 .
H1A C1 H1B 107.8 .
C3 C1 C2 113.11(15) 2_766
C3 C1 H1A 109.0 2_766
C3 C1 H1B 109.0 2_766
C16 O3 H3 109.5 .
C5 C4 C2 119.43(17) .
C9 C4 C2 123.57(17) .
C9 C4 C5 116.91(18) .
C4 C5 H5 119.1 .
C6 C5 C4 121.85(19) .
C6 C5 H5 119.1 .
C5 C6 H6 120.2 .
C7 C6 C5 119.64(19) .
C7 C6 H6 120.2 .
C15 C10 C2 120.03(17) .
C11 C10 C2 123.22(18) .
C11 C10 C15 116.76(19) .
C13 C12 H12 120.1 .
C13 C12 C11 119.72(19) .
C11 C12 H12 120.1 .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.45(15) 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 .
C14 C15 C10 122.33(19) .
C14 C15 H15 118.8 .
C15 C14 H14 120.3 .
C13 C14 C15 119.4(2) .
C13 C14 H14 120.3 .
C8 C7 O1 116.93(18) .
C6 C7 O1 122.96(19) .
C6 C7 C8 120.11(18) .
C8 C9 H9 119.1 .
C4 C9 C8 121.72(19) .
C4 C9 H9 119.1 .
C12 C13 O2 122.27(19) .
C14 C13 O2 117.67(19) .
C14 C13 C12 120.05(19) .
C10 C11 C12 121.7(2) .
C10 C11 H11 119.2 .
C12 C11 H11 119.2 .
O3 C16 C17 113.7(3) .
C21 C16 O3 122.2(3) .
C21 C16 C17 124.1(3) .
C16 C21 H21 120.1 .
C16 C21 C20 119.7(3) .
C20 C21 H21 120.1 .
C16 C17 C22 122.3(3) .
C18 C17 C16 114.4(3) .
C18 C17 C22 123.3(3) .
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 118.6 .
C19 C18 C17 122.8(3) .
C19 C18 H18 118.6 .
C18 C19 H19 119.2 .
C20 C19 C18 121.7(4) .
C20 C19 H19 119.2 .
C21 C20 H20 121.3 .
C19 C20 C21 117.3(4) .
C19 C20 H20 121.3 .
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 1.384(2) .
O2 H2 0.8300 .
O2 C13 1.388(2) .
C2 C1 1.552(3) .
C2 C4 1.543(3) .
C2 C10 1.544(3) .
C2 C3 1.541(3) .
C8 H8 0.9400 .
C8 C7 1.376(3) .
C8 C9 1.391(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 C3 1.528(3) 2_766
O3 H3 0.8300 .
O3 C16 1.379(4) .
C4 C5 1.395(3) .
C4 C9 1.387(3) .
C5 H5 0.9400 .
C5 C6 1.387(3) .
C6 H6 0.9400 .
C6 C7 1.374(3) .
C10 C15 1.394(3) .
C10 C11 1.392(3) .
C12 H12 0.9400 .
C12 C13 1.381(3) .
C12 C11 1.395(3) .
C3 C1 1.528(3) 2_766
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C15 H15 0.9400 .
C15 C14 1.387(3) .
C14 H14 0.9400 .
C14 C13 1.381(3) .
C9 H9 0.9400 .
C11 H11 0.9400 .
C16 C21 1.331(4) .
C16 C17 1.413(4) .
C21 H21 0.9400 .
C21 C20 1.444(5) .
C17 C22 1.436(5) .
C17 C18 1.401(5) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 H22C 0.9700 .
C18 H18 0.9400 .
C18 C19 1.367(6) .
C19 H19 0.9400 .
C19 C20 1.358(6) .
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 175.77(19) .
C2 C4 C9 C8 -175.99(19) .
C2 C10 C15 C14 -178.92(18) .
C2 C10 C11 C12 179.05(18) .
C1 C2 C4 C5 166.98(18) .
C1 C2 C4 C9 -16.4(3) .
C1 C2 C10 C15 67.5(2) .
C1 C2 C10 C11 -112.2(2) .
C1 C2 C3 C1 -55.4(2) 2_766
O3 C16 C21 C20 -179.2(3) .
O3 C16 C17 C22 -0.6(4) .
O3 C16 C17 C18 179.1(3) .
C4 C2 C1 C3 -66.3(2) 2_766
C4 C2 C10 C15 -54.3(2) .
C4 C2 C10 C11 126.0(2) .
C4 C2 C3 C1 67.03(19) 2_766
C4 C5 C6 C7 0.2(3) .
C5 C4 C9 C8 0.7(3) .
C5 C6 C7 O1 -178.27(19) .
C5 C6 C7 C8 1.1(3) .
C10 C2 C1 C3 175.10(15) 2_766
C10 C2 C4 C5 -73.8(2) .
C10 C2 C4 C9 102.8(2) .
C10 C2 C3 C1 -173.19(15) 2_766
C10 C15 C14 C13 -0.5(3) .
C3 C2 C1 C3 55.2(2) 2_766
C3 C2 C4 C5 48.5(2) .
C3 C2 C4 C9 -134.9(2) .
C3 C2 C10 C15 -176.21(17) .
C3 C2 C10 C11 4.0(3) .
C15 C10 C11 C12 -0.7(3) .
C15 C14 C13 O2 -179.19(19) .
C15 C14 C13 C12 0.0(3) .
C7 C8 C9 C4 0.6(3) .
C9 C8 C7 O1 178.0(2) .
C9 C8 C7 C6 -1.5(3) .
C9 C4 C5 C6 -1.0(3) .
C13 C12 C11 C10 0.2(3) .
C11 C10 C15 C14 0.8(3) .
C11 C12 C13 O2 179.3(2) .
C11 C12 C13 C14 0.1(3) .
C16 C21 C20 C19 -0.1(6) .
C16 C17 C18 C19 0.5(5) .
C21 C16 C17 C22 -179.9(3) .
C21 C16 C17 C18 -0.2(4) .
C17 C16 C21 C20 0.1(5) .
C17 C18 C19 C20 -0.6(7) .
C22 C17 C18 C19 -179.8(4) .
C18 C19 C20 C21 0.4(7) .
