#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512787.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_4512787
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-165K
_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                99.136(5)
_cell_angle_beta                 98.214(5)
_cell_angle_gamma                101.257(5)
_cell_formula_units_Z            1
_cell_length_a                   6.1775(3)
_cell_length_b                   10.8049(6)
_cell_length_c                   15.6264(9)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    165(2)
_cell_measurement_theta_max      29.0722
_cell_measurement_theta_min      3.8827
_cell_volume                     993.56(10)
_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 0.992
_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  0.0227
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9052
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         3.89
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9668
_exptl_absorpt_correction_T_min  0.9668
_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    1.275
_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         0.307
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0546
_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)+(0.1070P)²+0.1534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1785
_reflns_number_gt                3535
_reflns_number_total             4531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-mc-combined.cif
_cod_data_source_block           1-mc-165k
_cod_original_cell_volume        993.57(9)
_cod_original_formula_sum        'C48.90 H52 O7.70'
_cod_database_code               4512787
#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 0.2264(2) 0.89138(11) 0.18577(9) 0.0320(3) Uani 1 1 d .
H1 H 0.1344 0.9367 0.1832 0.048 Uiso 1 1 calc GR
O2 O -0.0630(2) 0.04537(11) 0.17314(8) 0.0304(3) Uani 1 1 d .
H2 H -0.1936 0.0163 0.1483 0.046 Uiso 1 1 calc GR
O3 O 0.5381(2) 0.91538(12) 0.08216(9) 0.0349(3) Uani 1 1 d .
H3 H 0.4372 0.8951 0.1096 0.052 Uiso 1 1 calc GR
C2 C 0.0263(2) 0.52515(14) 0.40711(10) 0.0190(3) Uani 1 1 d .
C1 C -0.1863(2) 0.53284(15) 0.44680(10) 0.0198(3) Uani 1 1 d .
H1A H -0.1749 0.6208 0.4757 0.024 Uiso 1 1 calc R
H1B H -0.3158 0.5096 0.3996 0.024 Uiso 1 1 calc R
C4 C 0.0730(2) 0.62545(14) 0.34833(10) 0.0204(3) Uani 1 1 d .
C3 C 0.2219(2) 0.55558(14) 0.48669(10) 0.0190(3) Uani 1 1 d .
H3A H 0.3594 0.5481 0.4651 0.023 Uiso 1 1 calc R
H3B H 0.2406 0.6439 0.5165 0.023 Uiso 1 1 calc R
C10 C -0.0007(2) 0.39155(14) 0.34873(10) 0.0196(3) Uani 1 1 d .
C14 C -0.2229(3) 0.22236(15) 0.22866(11) 0.0248(4) Uani 1 1 d .
H14 H -0.3557 0.1886 0.1884 0.030 Uiso 1 1 calc R
C7 C 0.1732(3) 0.80576(15) 0.23987(11) 0.0245(3) Uani 1 1 d .
C12 C 0.1475(3) 0.20857(16) 0.29193(11) 0.0271(4) Uani 1 1 d .
H12 H 0.2640 0.1654 0.2940 0.033 Uiso 1 1 calc R
C15 C -0.1966(2) 0.33726(15) 0.28665(11) 0.0235(3) Uani 1 1 d .
H15 H -0.3136 0.3800 0.2843 0.028 Uiso 1 1 calc R
C17 C 0.3677(3) 0.70325(15) -0.00430(11) 0.0259(4) Uani 1 1 d .
H17 H 0.2416 0.7004 0.0222 0.031 Uiso 1 1 calc R
C8 C 0.3094(3) 0.72000(15) 0.25277(11) 0.0256(4) Uani 1 1 d .
H8 H 0.4345 0.7220 0.2258 0.031 Uiso 1 1 calc R
C6 C -0.0127(3) 0.80199(16) 0.28070(12) 0.0288(4) Uani 1 1 d .
H6 H -0.1051 0.8591 0.2723 0.035 Uiso 1 1 calc R
C13 C -0.0493(3) 0.15768(14) 0.23107(11) 0.0233(3) Uani 1 1 d .
C21 C 0.7336(3) 0.81738(17) -0.01883(12) 0.0311(4) Uani 1 1 d .
H21 H 0.8508 0.8899 -0.0030 0.037 Uiso 1 1 calc R
C11 C 0.1702(2) 0.32335(15) 0.34945(11) 0.0244(3) Uani 1 1 d .
H11 H 0.3030 0.3563 0.3899 0.029 Uiso 1 1 calc R
C20 C 0.7455(3) 0.71371(18) -0.08152(12) 0.0327(4) Uani 1 1 d .
H20 H 0.8720 0.7165 -0.1077 0.039 Uiso 1 1 calc R
C9 C 0.2583(3) 0.63148(15) 0.30591(11) 0.0245(3) Uani 1 1 d .
H9 H 0.3503 0.5740 0.3137 0.029 Uiso 1 1 calc R
C16 C 0.5445(3) 0.81109(16) 0.01973(11) 0.0259(4) Uani 1 1 d .
C5 C -0.0604(3) 0.71268(16) 0.33416(11) 0.0263(4) Uani 1 1 d .
H5 H -0.1852 0.7112 0.3613 0.032 Uiso 1 1 calc R
C18 C 0.3787(3) 0.59950(16) -0.06786(11) 0.0285(4) Uani 1 1 d .
C19 C 0.5703(3) 0.60599(17) -0.10554(12) 0.0316(4) Uani 1 1 d .
H19 H 0.5811 0.5371 -0.1474 0.038 Uiso 1 1 calc R
C22 C 0.1855(3) 0.48424(18) -0.09623(13) 0.0390(5) Uani 1 1 d .
H22A H 0.2245 0.4132 -0.0725 0.059 Uiso 1 1 calc GR
H22B H 0.1531 0.4617 -0.1594 0.059 Uiso 1 1 calc GR
H22C H 0.0558 0.5043 -0.0749 0.059 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 105.71(12) .
C1 C2 C10 110.56(12) .
C4 C2 C1 111.72(12) .
C4 C2 C3 108.83(12) .
C4 C2 C10 107.00(11) .
C10 C2 C3 113.10(12) .
C2 C1 H1A 109.1 .
C2 C1 H1B 109.1 .
H1A C1 H1B 107.8 .
C3 C1 C2 112.66(12) 2_566
C3 C1 H1A 109.1 2_566
C3 C1 H1B 109.1 2_566
C9 C4 C2 119.65(13) .
C5 C4 C2 123.59(13) .
C5 C4 C9 116.77(14) .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.52(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 120.13(13) .
C15 C10 C11 116.50(14) .
C11 C10 C2 123.19(13) .
C15 C14 H14 120.3 .
C15 C14 C13 119.45(14) .
C13 C14 H14 120.3 .
O1 C7 C8 118.40(14) .
O1 C7 C6 122.05(14) .
C8 C7 C6 119.55(15) .
C13 C12 H12 120.0 .
C11 C12 H12 120.0 .
C11 C12 C13 119.93(14) .
C10 C15 H15 118.8 .
C14 C15 C10 122.42(14) .
C14 C15 H15 118.8 .
C16 C17 H17 119.9 .
C16 C17 C18 120.30(15) .
C18 C17 H17 119.9 .
C7 C8 H8 120.1 .
C9 C8 C7 119.72(14) .
C9 C8 H8 120.1 .
C7 C6 H6 120.1 .
C7 C6 C5 119.80(15) .
C5 C6 H6 120.1 .
O2 C13 C14 121.99(14) .
O2 C13 C12 118.27(14) .
C12 C13 C14 119.72(15) .
C20 C21 H21 120.6 .
C16 C21 H21 120.6 .
C16 C21 C20 118.88(16) .
C10 C11 H11 119.0 .
C12 C11 C10 121.98(14) .
C12 C11 H11 119.0 .
C21 C20 H20 119.7 .
C19 C20 C21 120.56(16) .
C19 C20 H20 119.7 .
C4 C9 H9 118.9 .
C8 C9 C4 122.20(14) .
C8 C9 H9 118.9 .
O3 C16 C17 121.63(14) .
O3 C16 C21 117.54(14) .
C21 C16 C17 120.83(16) .
C4 C5 H5 119.0 .
C6 C5 C4 121.96(14) .
C6 C5 H5 119.0 .
C17 C18 C22 120.66(16) .
C19 C18 C17 118.51(15) .
C19 C18 C22 120.81(16) .
C20 C19 C18 120.92(16) .
C20 C19 H19 119.5 .
C18 C19 H19 119.5 .
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 1.3738(19) .
O2 H2 0.8200 .
O2 C13 1.3741(19) .
O3 H3 0.8200 .
O3 C16 1.379(2) .
C2 C1 1.541(2) .
C2 C4 1.540(2) .
C2 C3 1.549(2) .
C2 C10 1.545(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C3 1.530(2) 2_566
C4 C9 1.398(2) .
C4 C5 1.391(2) .
C3 C1 1.530(2) 2_566
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C10 C15 1.399(2) .
C10 C11 1.400(2) .
C14 H14 0.9300 .
C14 C15 1.382(2) .
C14 C13 1.389(2) .
C7 C8 1.386(2) .
C7 C6 1.388(2) .
C12 H12 0.9300 .
C12 C13 1.388(2) .
C12 C11 1.381(2) .
C15 H15 0.9300 .
C17 H17 0.9300 .
C17 C16 1.392(2) .
C17 C18 1.394(2) .
C8 H8 0.9300 .
C8 C9 1.383(2) .
C6 H6 0.9300 .
C6 C5 1.390(2) .
C21 H21 0.9300 .
C21 C20 1.387(3) .
C21 C16 1.384(2) .
C11 H11 0.9300 .
C20 H20 0.9300 .
C20 C19 1.386(3) .
C9 H9 0.9300 .
C5 H5 0.9300 .
C18 C19 1.390(3) .
C18 C22 1.505(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 -179.11(14) .
O1 C7 C6 C5 179.38(15) .
C2 C4 C9 C8 -179.60(14) .
C2 C4 C5 C6 179.92(15) .
C2 C10 C15 C14 175.38(13) .
C2 C10 C11 C12 -175.07(14) .
C1 C2 C4 C9 -179.27(13) .
C1 C2 C4 C5 0.7(2) .
C1 C2 C3 C1 56.03(16) 2_566
C1 C2 C10 C15 47.28(18) .
C1 C2 C10 C11 -137.71(15) .
C4 C2 C1 C3 -173.71(12) 2_566
C4 C2 C3 C1 176.16(11) 2_566
C4 C2 C10 C15 -74.59(16) .
C4 C2 C10 C11 100.43(16) .
C3 C2 C1 C3 -55.49(17) 2_566
C3 C2 C4 C9 64.39(17) .
C3 C2 C4 C5 -115.67(16) .
C3 C2 C10 C15 165.59(13) .
C3 C2 C10 C11 -19.4(2) .
C10 C2 C1 C3 67.25(15) 2_566
C10 C2 C4 C9 -58.14(17) .
C10 C2 C4 C5 121.80(16) .
C10 C2 C3 C1 -65.07(15) 2_566
C7 C8 C9 C4 -0.5(3) .
C7 C6 C5 C4 -0.1(3) .
C15 C10 C11 C12 0.1(2) .
C15 C14 C13 O2 -177.81(14) .
C15 C14 C13 C12 0.4(2) .
C17 C18 C19 C20 -0.9(3) .
C8 C7 C6 C5 0.1(3) .
C6 C7 C8 C9 0.2(3) .
C13 C14 C15 C10 -0.3(2) .
C13 C12 C11 C10 0.0(2) .
C21 C20 C19 C18 0.3(3) .
C11 C10 C15 C14 0.0(2) .
C11 C12 C13 O2 178.02(14) .
C11 C12 C13 C14 -0.3(2) .
C20 C21 C16 O3 179.68(16) .
C20 C21 C16 C17 -0.6(3) .
C9 C4 C5 C6 -0.1(2) .
C16 C17 C18 C19 0.7(2) .
C16 C17 C18 C22 -178.15(16) .
C16 C21 C20 C19 0.4(3) .
C5 C4 C9 C8 0.5(2) .
C18 C17 C16 O3 179.76(15) .
C18 C17 C16 C21 0.0(3) .
C22 C18 C19 C20 177.97(17) .
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 -0.019 0.000 0.500 168 14 ' '
