#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512786.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_4512786
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, 2.3(C7 H8 O), 0.7(C4 H8 O2)'
_chemical_formula_sum            'C48.9 H52 O7.7'
_chemical_formula_weight         762.91
_chemical_name_common            1-mc-120K
_chemical_name_systematic
;
 1,1,4,4,-tetrakis(4-hydroxyphenyl)cyclohexane.3-methylphenol.ethylacetate 
;
_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             2014-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                99.099(4)
_cell_angle_beta                 98.303(4)
_cell_angle_gamma                101.279(4)
_cell_formula_units_Z            1
_cell_length_a                   6.1632(3)
_cell_length_b                   10.7711(5)
_cell_length_c                   15.6073(8)
_cell_measurement_reflns_used    4177
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.1778
_cell_measurement_theta_min      3.7010
_cell_volume                     986.70(9)
_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 0.992
_diffrn_measured_fraction_theta_max 0.852
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10747
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_correction_T_min  0.9665
_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    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             407
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_platon_squeeze_details
;
0.15 molecules of 3-methylphenol and 0.35 
molecules of ethylacetate have been squeezed from the asymmetric unit
;
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0527
_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)+(0.0893P)²+0.3694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1667
_reflns_number_gt                3790
_reflns_number_total             4587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-mc-combined.cif
_cod_data_source_block           1-mc-120k
_cod_original_cell_volume        986.71(8)
_cod_original_formula_sum        'C48.90 H52 O7.70'
_cod_database_code               4512786
#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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C15(H15), C17(H17), C8(H8), C6(H6), C21(H21), C11(H11),
 C20(H20), C9(H9), C5(H5), C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.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 0.2273(2) 0.89275(11) 0.18540(8) 0.0237(3) Uani 1 1 d .
H1 H 0.1348 0.9379 0.1825 0.036 Uiso 1 1 calc GR
O2 O -0.06302(19) 0.04582(11) 0.17203(8) 0.0225(3) Uani 1 1 d .
H2 H -0.1941 0.0162 0.1475 0.034 Uiso 1 1 calc GR
O3 O 0.5377(2) 0.91587(11) 0.08133(8) 0.0254(3) Uani 1 1 d .
H3 H 0.4376 0.8955 0.1092 0.038 Uiso 1 1 calc GR
C2 C 0.0265(2) 0.52536(14) 0.40706(9) 0.0133(3) Uani 1 1 d .
C1 C -0.1867(2) 0.53344(14) 0.44683(10) 0.0138(3) Uani 1 1 d .
H1A H -0.1745 0.6216 0.4760 0.017 Uiso 1 1 calc R
H1B H -0.3166 0.5106 0.3996 0.017 Uiso 1 1 calc R
C4 C 0.0737(2) 0.62622(14) 0.34847(10) 0.0146(3) Uani 1 1 d .
C3 C 0.2226(2) 0.55580(14) 0.48685(9) 0.0137(3) Uani 1 1 d .
H3A H 0.3605 0.5486 0.4654 0.016 Uiso 1 1 calc R
H3B H 0.2410 0.6442 0.5169 0.016 Uiso 1 1 calc R
C10 C -0.0003(2) 0.39198(14) 0.34865(10) 0.0142(3) Uani 1 1 d .
C14 C -0.2240(2) 0.22244(15) 0.22799(10) 0.0178(3) Uani 1 1 d .
H14 H -0.3570 0.1888 0.1874 0.021 Uiso 1 1 calc R
C7 C 0.1737(3) 0.80690(15) 0.23963(10) 0.0177(3) Uani 1 1 d .
C12 C 0.1480(3) 0.20854(15) 0.29144(11) 0.0205(3) Uani 1 1 d .
H12 H 0.2649 0.1654 0.2933 0.025 Uiso 1 1 calc R
C15 C -0.1974(2) 0.33762(15) 0.28662(10) 0.0170(3) Uani 1 1 d .
H15 H -0.3149 0.3803 0.2847 0.020 Uiso 1 1 calc R
C17 C 0.3661(3) 0.70287(15) -0.00463(10) 0.0189(3) Uani 1 1 d .
H17 H 0.2396 0.7003 0.0217 0.023 Uiso 1 1 calc R
C8 C 0.3110(2) 0.72078(15) 0.25251(11) 0.0189(3) Uani 1 1 d .
H8 H 0.4363 0.7228 0.2255 0.023 Uiso 1 1 calc R
C6 C -0.0117(3) 0.80366(16) 0.28069(11) 0.0219(3) Uani 1 1 d .
H6 H -0.1036 0.8613 0.2724 0.026 Uiso 1 1 calc R
C13 C -0.0496(3) 0.15774(14) 0.23051(10) 0.0172(3) Uani 1 1 d .
C21 C 0.7339(3) 0.81711(16) -0.01946(11) 0.0223(3) Uani 1 1 d .
H21 H 0.8512 0.8900 -0.0040 0.027 Uiso 1 1 calc R
C11 C 0.1707(2) 0.32350(15) 0.34945(10) 0.0178(3) Uani 1 1 d .
H11 H 0.3035 0.3562 0.3902 0.021 Uiso 1 1 calc R
C20 C 0.7454(3) 0.71211(17) -0.08192(11) 0.0241(4) Uani 1 1 d .
H20 H 0.8724 0.7144 -0.1079 0.029 Uiso 1 1 calc R
C9 C 0.2597(2) 0.63177(15) 0.30598(10) 0.0176(3) Uani 1 1 d .
H9 H 0.3517 0.5740 0.3138 0.021 Uiso 1 1 calc R
C16 C 0.5440(3) 0.81096(15) 0.01926(10) 0.0189(3) Uani 1 1 d .
C5 C -0.0600(3) 0.71387(16) 0.33445(11) 0.0197(3) Uani 1 1 d .
H5 H -0.1849 0.7125 0.3616 0.024 Uiso 1 1 calc R
C18 C 0.3776(3) 0.59854(16) -0.06806(11) 0.0204(3) Uani 1 1 d .
C19 C 0.5696(3) 0.60431(16) -0.10568(11) 0.0226(3) Uani 1 1 d .
H19 H 0.5800 0.5348 -0.1474 0.027 Uiso 1 1 calc R
C22 C 0.1835(3) 0.48280(17) -0.09622(12) 0.0278(4) Uani 1 1 d .
H22A H 0.2278 0.4094 -0.0773 0.042 Uiso 1 1 calc GR
H22B H 0.1407 0.4652 -0.1593 0.042 Uiso 1 1 calc GR
H22C H 0.0582 0.5001 -0.0700 0.042 Uiso 1 1 calc GR
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 .
C16 O3 H3 109.5 .
C1 C2 C3 105.62(11) .
C4 C2 C1 111.59(12) .
C4 C2 C3 108.74(11) .
C4 C2 C10 107.00(11) .
C10 C2 C1 110.82(11) .
C10 C2 C3 113.13(12) .
C2 C1 H1A 109.1 .
C2 C1 H1B 109.1 .
H1A C1 H1B 107.8 .
C3 C1 C2 112.46(12) 2_566
C3 C1 H1A 109.1 2_566
C3 C1 H1B 109.1 2_566
C9 C4 C2 119.43(13) .
C5 C4 C2 123.51(13) .
C5 C4 C9 117.06(14) .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.43(12) 2_566
C1 C3 H3A 108.9 2_566
C1 C3 H3B 108.9 2_566
H3A C3 H3B 107.7 .
C15 C10 C2 119.97(13) .
C11 C10 C2 123.26(13) .
C11 C10 C15 116.62(14) .
C15 C14 H14 120.4 .
C15 C14 C13 119.22(14) .
C13 C14 H14 120.4 .
O1 C7 C8 118.11(13) .
O1 C7 C6 122.11(14) .
C6 C7 C8 119.78(14) .
C13 C12 H12 120.1 .
C11 C12 H12 120.1 .
C11 C12 C13 119.84(14) .
C10 C15 H15 118.8 .
C14 C15 C10 122.40(14) .
C14 C15 H15 118.8 .
C16 C17 H17 120.0 .
C16 C17 C18 120.03(14) .
C18 C17 H17 120.0 .
C7 C8 H8 120.2 .
C9 C8 C7 119.52(14) .
C9 C8 H8 120.2 .
C7 C6 H6 120.1 .
C7 C6 C5 119.88(15) .
C5 C6 H6 120.1 .
O2 C13 C14 121.83(14) .
O2 C13 C12 118.19(14) .
C12 C13 C14 119.94(14) .
C20 C21 H21 120.6 .
C16 C21 H21 120.6 .
C16 C21 C20 118.73(15) .
C10 C11 H11 119.0 .
C12 C11 C10 121.97(14) .
C12 C11 H11 119.0 .
C21 C20 H20 119.7 .
C19 C20 C21 120.58(15) .
C19 C20 H20 119.7 .
C4 C9 H9 119.0 .
C8 C9 C4 122.03(14) .
C8 C9 H9 119.0 .
O3 C16 C17 121.54(14) .
O3 C16 C21 117.52(14) .
C21 C16 C17 120.94(15) .
C4 C5 C6 121.72(14) .
C4 C5 H5 119.1 .
C6 C5 H5 119.1 .
C17 C18 C22 120.45(15) .
C19 C18 C17 118.82(15) .
C19 C18 C22 120.72(15) .
C20 C19 C18 120.88(15) .
C20 C19 H19 119.6 .
C18 C19 H19 119.6 .
C18 C22 H22A 109.5 .
C18 C22 H22B 109.5 .
C18 C22 H22C 109.5 .
H22A C22 H22B 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8200 .
O1 C7 1.3746(18) .
O2 H2 0.8200 .
O2 C13 1.3727(18) .
O3 H3 0.8200 .
O3 C16 1.3779(19) .
C2 C1 1.5435(19) .
C2 C4 1.539(2) .
C2 C3 1.549(2) .
C2 C10 1.540(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C3 1.530(2) 2_566
C4 C9 1.401(2) .
C4 C5 1.391(2) .
C3 C1 1.530(2) 2_566
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C10 C15 1.400(2) .
C10 C11 1.399(2) .
C14 H14 0.9300 .
C14 C15 1.386(2) .
C14 C13 1.390(2) .
C7 C8 1.391(2) .
C7 C6 1.385(2) .
C12 H12 0.9300 .
C12 C13 1.388(2) .
C12 C11 1.383(2) .
C15 H15 0.9300 .
C17 H17 0.9300 .
C17 C16 1.394(2) .
C17 C18 1.395(2) .
C8 H8 0.9300 .
C8 C9 1.388(2) .
C6 H6 0.9300 .
C6 C5 1.394(2) .
C21 H21 0.9300 .
C21 C20 1.392(2) .
C21 C16 1.388(2) .
C11 H11 0.9300 .
C20 H20 0.9300 .
C20 C19 1.384(2) .
C9 H9 0.9300 .
C5 H5 0.9300 .
C18 C19 1.390(2) .
C18 C22 1.507(2) .
C19 H19 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
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
O1 C7 C8 C9 -179.18(14) .
O1 C7 C6 C5 179.40(15) .
C2 C4 C9 C8 -179.85(13) .
C2 C4 C5 C6 -179.89(14) .
C2 C10 C15 C14 175.19(13) .
C2 C10 C11 C12 -174.90(14) .
C1 C2 C4 C9 -179.23(13) .
C1 C2 C4 C5 0.5(2) .
C1 C2 C3 C1 56.39(16) 2_566
C1 C2 C10 C15 46.93(18) .
C1 C2 C10 C11 -137.65(14) .
C4 C2 C1 C3 -173.78(11) 2_566
C4 C2 C3 C1 176.28(11) 2_566
C4 C2 C10 C15 -74.94(16) .
C4 C2 C10 C11 100.49(16) .
C3 C2 C1 C3 -55.78(16) 2_566
C3 C2 C4 C9 64.66(17) .
C3 C2 C4 C5 -115.58(16) .
C3 C2 C10 C15 165.33(13) .
C3 C2 C10 C11 -19.24(19) .
C10 C2 C1 C3 67.09(15) 2_566
C10 C2 C4 C9 -57.85(17) .
C10 C2 C4 C5 121.90(15) .
C10 C2 C3 C1 -64.99(15) 2_566
C7 C8 C9 C4 -0.6(2) .
C7 C6 C5 C4 0.1(3) .
C15 C10 C11 C12 0.7(2) .
C15 C14 C13 O2 -177.60(14) .
C15 C14 C13 C12 0.2(2) .
C17 C18 C19 C20 -1.0(2) .
C8 C7 C6 C5 -0.2(2) .
C6 C7 C8 C9 0.5(2) .
C13 C14 C15 C10 0.1(2) .
C13 C12 C11 C10 -0.4(2) .
C21 C20 C19 C18 0.2(3) .
C11 C10 C15 C14 -0.5(2) .
C11 C12 C13 O2 177.80(14) .
C11 C12 C13 C14 0.0(2) .
C20 C21 C16 O3 179.56(15) .
C20 C21 C16 C17 -1.0(3) .
C9 C4 C5 C6 -0.1(2) .
C16 C17 C18 C19 0.7(2) .
C16 C17 C18 C22 -178.27(16) .
C16 C21 C20 C19 0.8(3) .
C5 C4 C9 C8 0.4(2) .
C18 C17 C16 O3 179.69(15) .
C18 C17 C16 C21 0.3(2) .
C22 C18 C19 C20 178.02(16) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.018 0.000 0.500 164 14 ' '
