#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512790.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_4512790
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-298K
_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                99.286(5)
_cell_angle_beta                 97.955(5)
_cell_angle_gamma                101.210(5)
_cell_formula_units_Z            1
_cell_length_a                   6.2326(3)
_cell_length_b                   10.8899(7)
_cell_length_c                   15.7278(11)
_cell_measurement_reflns_used    2979
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.0001
_cell_measurement_theta_min      3.8266
_cell_volume                     1017.38(11)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.864
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0390
_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       -21
_diffrn_reflns_number            11646
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.9675
_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    1.245
_exptl_crystal_density_method    'not measured'
_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         0.321
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0613
_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)+(0.1107P)²+0.0936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.1990
_reflns_number_gt                3317
_reflns_number_total             4695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-mc-combined.cif
_cod_data_source_block           1-mc-298k
_cod_original_formula_sum        'C48.90 H52 O7.70'
_cod_database_code               4512790
#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 0.2216(3) 0.88676(13) 0.18656(10) 0.0512(4) Uani 1 1 d .
H1 H 0.1368 0.9357 0.1877 0.077 Uiso 1 1 calc GR
O2 O -0.0630(2) 0.04382(13) 0.17746(10) 0.0498(4) Uani 1 1 d .
H2 H -0.1928 0.0139 0.1540 0.075 Uiso 1 1 calc GR
O3 O 0.5407(3) 0.91393(14) 0.08580(11) 0.0601(5) Uani 1 1 d .
H3 H 0.4330 0.8957 0.1096 0.090 Uiso 1 1 calc GR
C2 C 0.0260(2) 0.52343(15) 0.40714(10) 0.0273(4) Uani 1 1 d .
C1 C -0.1844(3) 0.53150(16) 0.44714(11) 0.0298(4) Uani 1 1 d .
H1A H -0.1735 0.6191 0.4753 0.036 Uiso 1 1 calc R
H1B H -0.3129 0.5077 0.4005 0.036 Uiso 1 1 calc R
C4 C 0.0710(3) 0.62275(15) 0.34805(11) 0.0301(4) Uani 1 1 d .
C3 C 0.2192(2) 0.55474(16) 0.48600(11) 0.0293(4) Uani 1 1 d .
H3A H 0.3555 0.5470 0.4645 0.035 Uiso 1 1 calc R
H3B H 0.2373 0.6427 0.5150 0.035 Uiso 1 1 calc R
C10 C 0.0000(3) 0.39026(15) 0.34913(10) 0.0292(4) Uani 1 1 d .
C14 C -0.2195(3) 0.22139(17) 0.23103(12) 0.0396(4) Uani 1 1 d .
H14 H -0.3506 0.1879 0.1910 0.048 Uiso 1 1 calc R
C7 C 0.1688(3) 0.80100(17) 0.24038(12) 0.0377(4) Uani 1 1 d .
C12 C 0.1459(3) 0.20834(18) 0.29360(13) 0.0429(5) Uani 1 1 d .
H12 H 0.2619 0.1660 0.2953 0.052 Uiso 1 1 calc R
C15 C -0.1935(3) 0.33635(17) 0.28812(12) 0.0357(4) Uani 1 1 d .
H15 H -0.3091 0.3790 0.2857 0.043 Uiso 1 1 calc R
C17 C 0.3717(3) 0.70521(19) -0.00269(13) 0.0429(5) Uani 1 1 d .
H17 H 0.2464 0.7015 0.0236 0.051 Uiso 1 1 calc R
C8 C 0.3044(3) 0.71679(19) 0.25316(13) 0.0420(5) Uani 1 1 d .
H8 H 0.4288 0.7191 0.2264 0.050 Uiso 1 1 calc R
C6 C -0.0156(3) 0.79624(18) 0.28031(14) 0.0440(5) Uani 1 1 d .
H6 H -0.1082 0.8522 0.2718 0.053 Uiso 1 1 calc R
C13 C -0.0492(3) 0.15673(16) 0.23388(12) 0.0362(4) Uani 1 1 d .
C21 C 0.7324(4) 0.8197(2) -0.01714(15) 0.0533(5) Uani 1 1 d .
H21 H 0.8477 0.8919 -0.0014 0.064 Uiso 1 1 calc R
C11 C 0.1681(3) 0.32251(18) 0.35048(12) 0.0376(4) Uani 1 1 d .
H11 H 0.2989 0.3551 0.3908 0.045 Uiso 1 1 calc R
C20 C 0.7437(4) 0.7182(2) -0.08027(15) 0.0587(6) Uani 1 1 d .
H20 H 0.8692 0.7218 -0.1064 0.070 Uiso 1 1 calc R
C9 C 0.2541(3) 0.62930(18) 0.30586(13) 0.0387(4) Uani 1 1 d .
H9 H 0.3458 0.5726 0.3135 0.046 Uiso 1 1 calc R
C16 C 0.5457(3) 0.81174(19) 0.02230(13) 0.0433(5) Uani 1 1 d .
C5 C -0.0623(3) 0.70756(18) 0.33323(13) 0.0405(4) Uani 1 1 d .
H5 H -0.1874 0.7051 0.3596 0.049 Uiso 1 1 calc R
C18 C 0.3837(4) 0.6043(2) -0.06657(13) 0.0472(5) Uani 1 1 d .
C19 C 0.5721(4) 0.6120(2) -0.10505(14) 0.0544(6) Uani 1 1 d .
H19 H 0.5824 0.5448 -0.1479 0.065 Uiso 1 1 calc R
C22 C 0.1925(5) 0.4894(2) -0.09523(17) 0.0679(7) Uani 1 1 d .
H22A H 0.1323 0.4684 -0.0451 0.102 Uiso 1 1 calc GR
H22B H 0.2442 0.4184 -0.1231 0.102 Uiso 1 1 calc GR
H22C H 0.0792 0.5085 -0.1357 0.102 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 C4 111.56(13) .
C1 C2 C3 105.41(13) .
C1 C2 C10 110.76(13) .
C4 C2 C3 108.94(13) .
C4 C2 C10 106.89(12) .
C3 C2 C10 113.35(13) .
C2 C1 H1A 109.0 .
C2 C1 H1B 109.0 .
H1A C1 H1B 107.8 .
C3 C1 C2 112.91(13) 2_566
C3 C1 H1A 109.0 2_566
C3 C1 H1B 109.0 2_566
C9 C4 C2 119.77(14) .
C5 C4 C2 123.76(14) .
C5 C4 C9 116.47(16) .
C2 C3 H3A 108.8 .
C2 C3 H3B 108.8 .
C1 C3 C2 113.66(13) 2_566
C1 C3 H3A 108.8 2_566
C1 C3 H3B 108.8 2_566
H3A C3 H3B 107.7 .
C15 C10 C2 119.95(14) .
C11 C10 C2 123.19(15) .
C11 C10 C15 116.74(15) .
C15 C14 H14 120.2 .
C13 C14 H14 120.2 .
C13 C14 C15 119.59(17) .
C8 C7 O1 118.43(16) .
C6 C7 O1 122.02(16) .
C6 C7 C8 119.55(17) .
C13 C12 H12 120.0 .
C11 C12 H12 120.0 .
C11 C12 C13 120.09(16) .
C10 C15 H15 118.9 .
C14 C15 C10 122.23(16) .
C14 C15 H15 118.9 .
C16 C17 H17 119.8 .
C18 C17 H17 119.8 .
C18 C17 C16 120.34(19) .
C7 C8 H8 120.2 .
C9 C8 C7 119.59(16) .
C9 C8 H8 120.2 .
C7 C6 H6 120.1 .
C7 C6 C5 119.77(17) .
C5 C6 H6 120.1 .
O2 C13 C14 122.26(17) .
O2 C13 C12 118.21(16) .
C14 C13 C12 119.50(16) .
C20 C21 H21 120.6 .
C20 C21 C16 118.7(2) .
C16 C21 H21 120.6 .
C10 C11 H11 119.1 .
C12 C11 C10 121.85(16) .
C12 C11 H11 119.1 .
C21 C20 H20 119.5 .
C19 C20 C21 121.0(2) .
C19 C20 H20 119.5 .
C4 C9 H9 118.8 .
C8 C9 C4 122.46(16) .
C8 C9 H9 118.8 .
O3 C16 C17 122.16(17) .
O3 C16 C21 117.28(18) .
C17 C16 C21 120.55(18) .
C4 C5 C6 122.15(16) .
C4 C5 H5 118.9 .
C6 C5 H5 118.9 .
C17 C18 C19 118.9(2) .
C17 C18 C22 120.4(2) .
C19 C18 C22 120.7(2) .
C20 C19 C18 120.51(19) .
C20 C19 H19 119.7 .
C18 C19 H19 119.7 .
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 1.382(2) .
O2 H2 0.8200 .
O2 C13 1.376(2) .
O3 H3 0.8200 .
O3 C16 1.378(2) .
C2 C1 1.542(2) .
C2 C4 1.546(2) .
C2 C3 1.547(2) .
C2 C10 1.550(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C3 1.529(2) 2_566
C4 C9 1.393(2) .
C4 C5 1.383(2) .
C3 C1 1.529(2) 2_566
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C10 C15 1.394(2) .
C10 C11 1.393(2) .
C14 H14 0.9300 .
C14 C15 1.385(2) .
C14 C13 1.383(2) .
C7 C8 1.382(3) .
C7 C6 1.380(3) .
C12 H12 0.9300 .
C12 C13 1.387(3) .
C12 C11 1.380(2) .
C15 H15 0.9300 .
C17 H17 0.9300 .
C17 C16 1.386(3) .
C17 C18 1.386(3) .
C8 H8 0.9300 .
C8 C9 1.380(3) .
C6 H6 0.9300 .
C6 C5 1.388(3) .
C21 H21 0.9300 .
C21 C20 1.381(3) .
C21 C16 1.387(3) .
C11 H11 0.9300 .
C20 H20 0.9300 .
C20 C19 1.376(3) .
C9 H9 0.9300 .
C5 H5 0.9300 .
C18 C19 1.388(3) .
C18 C22 1.509(3) .
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 -179.32(18) .
O1 C7 C6 C5 179.47(18) .
C2 C4 C9 C8 -179.22(17) .
C2 C4 C5 C6 179.43(17) .
C2 C10 C15 C14 175.93(16) .
C2 C10 C11 C12 -175.24(17) .
C1 C2 C4 C9 -179.72(15) .
C1 C2 C4 C5 -0.2(2) .
C1 C2 C3 C1 55.84(18) 2_566
C1 C2 C10 C15 47.2(2) .
C1 C2 C10 C11 -136.85(17) .
C4 C2 C1 C3 -173.45(13) 2_566
C4 C2 C3 C1 175.68(12) 2_566
C4 C2 C10 C15 -74.48(18) .
C4 C2 C10 C11 101.42(18) .
C3 C2 C1 C3 -55.36(19) 2_566
C3 C2 C4 C9 64.33(19) .
C3 C2 C4 C5 -116.11(18) .
C3 C2 C10 C15 165.49(15) .
C3 C2 C10 C11 -18.6(2) .
C10 C2 C1 C3 67.60(17) 2_566
C10 C2 C4 C9 -58.50(19) .
C10 C2 C4 C5 121.07(17) .
C10 C2 C3 C1 -65.46(17) 2_566
C7 C8 C9 C4 -0.6(3) .
C7 C6 C5 C4 0.3(3) .
C15 C10 C11 C12 0.8(3) .
C15 C14 C13 O2 -178.36(17) .
C15 C14 C13 C12 -0.4(3) .
C17 C18 C19 C20 -0.1(3) .
C8 C7 C6 C5 0.4(3) .
C6 C7 C8 C9 -0.2(3) .
C13 C14 C15 C10 0.0(3) .
C13 C12 C11 C10 -1.1(3) .
C21 C20 C19 C18 -0.3(4) .
C11 C10 C15 C14 -0.2(3) .
C11 C12 C13 O2 178.98(17) .
C11 C12 C13 C14 0.9(3) .
C20 C21 C16 O3 179.2(2) .
C20 C21 C16 C17 -1.5(3) .
C9 C4 C5 C6 -1.0(3) .
C16 C17 C18 C19 -0.2(3) .
C16 C17 C18 C22 -178.7(2) .
C16 C21 C20 C19 1.1(4) .
C5 C4 C9 C8 1.2(3) .
C18 C17 C16 O3 -179.74(19) .
C18 C17 C16 C21 1.0(3) .
C22 C18 C19 C20 178.4(2) .
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 0.500 176 14 ' '
