#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512789.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_4512789
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-255K
_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                99.230(5)
_cell_angle_beta                 98.051(5)
_cell_angle_gamma                101.221(5)
_cell_formula_units_Z            1
_cell_length_a                   6.2130(4)
_cell_length_b                   10.8567(6)
_cell_length_c                   15.6818(9)
_cell_measurement_reflns_used    3039
_cell_measurement_temperature    255(2)
_cell_measurement_theta_max      29.0450
_cell_measurement_theta_min      3.8633
_cell_volume                     1007.97(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      255(2)
_diffrn_measured_fraction_theta_full 0.993
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0398
_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       -19
_diffrn_reflns_number            10965
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9672
_exptl_absorpt_correction_T_min  0.9672
_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    1.257
_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         0.328
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0593
_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)+(0.1088P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                3431
_reflns_number_total             4629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1-mc-combined.cif
_cod_data_source_block           1-mc-255k
_cod_original_cell_volume        1007.97(10)
_cod_original_formula_sum        'C48.90 H52 O7.70'
_cod_database_code               4512789
#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 0.2232(2) 0.88827(13) 0.18620(10) 0.0437(4) Uani 1 1 d .
H1 H 0.1333 0.9344 0.1846 0.066 Uiso 1 1 calc GR
O2 O -0.0627(2) 0.04448(12) 0.17614(10) 0.0422(4) Uani 1 1 d .
H2 H -0.1915 0.0169 0.1502 0.063 Uiso 1 1 calc GR
O3 O 0.5398(2) 0.91450(14) 0.08445(10) 0.0500(4) Uani 1 1 d .
H3 H 0.4365 0.8947 0.1105 0.075 Uiso 1 1 calc GR
C2 C 0.0261(2) 0.52388(15) 0.40697(10) 0.0241(3) Uani 1 1 d .
C1 C -0.1851(2) 0.53227(15) 0.44695(11) 0.0248(3) Uani 1 1 d .
H1A H -0.1735 0.6200 0.4755 0.030 Uiso 1 1 calc R
H1B H -0.3140 0.5089 0.4002 0.030 Uiso 1 1 calc R
C4 C 0.0721(3) 0.62339(15) 0.34801(11) 0.0259(4) Uani 1 1 d .
C3 C 0.2204(2) 0.55510(15) 0.48629(10) 0.0242(3) Uani 1 1 d .
H3A H 0.3572 0.5476 0.4648 0.029 Uiso 1 1 calc R
H3B H 0.2384 0.6431 0.5156 0.029 Uiso 1 1 calc R
C10 C -0.0001(2) 0.39091(15) 0.34913(10) 0.0247(3) Uani 1 1 d .
C14 C -0.2206(3) 0.22156(16) 0.23013(12) 0.0328(4) Uani 1 1 d .
H14 H -0.3524 0.1878 0.1901 0.039 Uiso 1 1 calc R
C7 C 0.1700(3) 0.80288(16) 0.24024(12) 0.0314(4) Uani 1 1 d .
C12 C 0.1461(3) 0.20831(17) 0.29308(12) 0.0358(4) Uani 1 1 d .
H12 H 0.2620 0.1655 0.2951 0.043 Uiso 1 1 calc R
C15 C -0.1939(3) 0.33680(16) 0.28749(11) 0.0305(4) Uani 1 1 d .
H15 H -0.3097 0.3797 0.2848 0.037 Uiso 1 1 calc R
C17 C 0.3705(3) 0.70443(17) -0.00324(12) 0.0362(4) Uani 1 1 d .
H17 H 0.2454 0.7008 0.0234 0.043 Uiso 1 1 calc R
C8 C 0.3062(3) 0.71812(17) 0.25304(13) 0.0346(4) Uani 1 1 d .
H8 H 0.4307 0.7203 0.2261 0.042 Uiso 1 1 calc R
C6 C -0.0141(3) 0.79847(18) 0.28016(13) 0.0377(4) Uani 1 1 d .
H6 H -0.1067 0.8548 0.2715 0.045 Uiso 1 1 calc R
C13 C -0.0487(3) 0.15715(16) 0.23299(12) 0.0306(4) Uani 1 1 d .
C21 C 0.7328(3) 0.8190(2) -0.01748(14) 0.0438(5) Uani 1 1 d .
H21 H 0.8492 0.8911 -0.0012 0.053 Uiso 1 1 calc R
C11 C 0.1685(3) 0.32281(17) 0.35002(12) 0.0314(4) Uani 1 1 d .
H11 H 0.3002 0.3556 0.3903 0.038 Uiso 1 1 calc R
C20 C 0.7445(4) 0.7167(2) -0.08100(14) 0.0472(5) Uani 1 1 d .
H20 H 0.8700 0.7202 -0.1074 0.057 Uiso 1 1 calc R
C9 C 0.2560(3) 0.63013(17) 0.30613(12) 0.0322(4) Uani 1 1 d .
H9 H 0.3484 0.5735 0.3141 0.039 Uiso 1 1 calc R
C16 C 0.5450(3) 0.81155(18) 0.02105(12) 0.0362(4) Uani 1 1 d .
C5 C -0.0618(3) 0.70945(17) 0.33362(12) 0.0337(4) Uani 1 1 d .
H5 H -0.1866 0.7076 0.3604 0.040 Uiso 1 1 calc R
C18 C 0.3820(3) 0.60235(18) -0.06731(13) 0.0393(4) Uani 1 1 d .
C19 C 0.5715(4) 0.6098(2) -0.10526(13) 0.0450(5) Uani 1 1 d .
H19 H 0.5822 0.5418 -0.1476 0.054 Uiso 1 1 calc R
C22 C 0.1905(4) 0.4876(2) -0.09549(16) 0.0561(6) Uani 1 1 d .
H22A H 0.2339 0.4150 -0.0761 0.084 Uiso 1 1 calc GR
H22B H 0.1502 0.4695 -0.1583 0.084 Uiso 1 1 calc GR
H22C H 0.0652 0.5049 -0.0700 0.084 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 105.45(12) .
C4 C2 C1 111.59(12) .
C4 C2 C3 108.79(12) .
C4 C2 C10 106.98(12) .
C10 C2 C1 110.81(12) .
C10 C2 C3 113.28(12) .
C2 C1 H1A 109.1 .
C2 C1 H1B 109.1 .
H1A C1 H1B 107.8 .
C3 C1 C2 112.68(12) 2_566
C3 C1 H1A 109.1 2_566
C3 C1 H1B 109.1 2_566
C9 C4 C2 119.84(14) .
C5 C4 C2 123.45(14) .
C5 C4 C9 116.70(15) .
C2 C3 H3A 108.9 .
C2 C3 H3B 108.9 .
C1 C3 C2 113.49(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 120.12(14) .
C11 C10 C2 123.37(14) .
C11 C10 C15 116.34(15) .
C15 C14 H14 120.3 .
C15 C14 C13 119.31(15) .
C13 C14 H14 120.3 .
O1 C7 C8 118.17(15) .
C6 C7 O1 122.13(15) .
C6 C7 C8 119.69(16) .
C13 C12 H12 120.0 .
C11 C12 H12 120.0 .
C11 C12 C13 120.06(15) .
C10 C15 H15 118.7 .
C14 C15 C10 122.52(15) .
C14 C15 H15 118.7 .
C16 C17 H17 119.9 .
C16 C17 C18 120.26(17) .
C18 C17 H17 119.9 .
C7 C8 H8 120.2 .
C9 C8 C7 119.62(15) .
C9 C8 H8 120.2 .
C7 C6 H6 120.0 .
C7 C6 C5 119.91(16) .
C5 C6 H6 120.0 .
O2 C13 C14 121.99(16) .
O2 C13 C12 118.32(15) .
C12 C13 C14 119.68(16) .
C20 C21 H21 120.6 .
C16 C21 H21 120.6 .
C16 C21 C20 118.72(18) .
C10 C11 H11 119.0 .
C12 C11 C10 122.08(15) .
C12 C11 H11 119.0 .
C21 C20 H20 119.7 .
C19 C20 C21 120.58(19) .
C19 C20 H20 119.7 .
C4 C9 H9 118.8 .
C8 C9 C4 122.31(15) .
C8 C9 H9 118.8 .
O3 C16 C17 121.91(16) .
O3 C16 C21 117.18(16) .
C21 C16 C17 120.91(18) .
C4 C5 C6 121.77(15) .
C4 C5 H5 119.1 .
C6 C5 H5 119.1 .
C17 C18 C22 120.37(18) .
C19 C18 C17 118.62(18) .
C19 C18 C22 120.99(19) .
C20 C19 C18 120.90(19) .
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 1.378(2) .
O2 H2 0.8200 .
O2 C13 1.373(2) .
O3 H3 0.8200 .
O3 C16 1.380(2) .
C2 C1 1.543(2) .
C2 C4 1.542(2) .
C2 C3 1.551(2) .
C2 C10 1.543(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C3 1.532(2) 2_566
C4 C9 1.391(2) .
C4 C5 1.391(2) .
C3 C1 1.532(2) 2_566
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C10 C15 1.395(2) .
C10 C11 1.395(2) .
C14 H14 0.9300 .
C14 C15 1.385(2) .
C14 C13 1.385(2) .
C7 C8 1.385(2) .
C7 C6 1.376(2) .
C12 H12 0.9300 .
C12 C13 1.383(2) .
C12 C11 1.380(2) .
C15 H15 0.9300 .
C17 H17 0.9300 .
C17 C16 1.387(2) .
C17 C18 1.392(3) .
C8 H8 0.9300 .
C8 C9 1.384(2) .
C6 H6 0.9300 .
C6 C5 1.394(2) .
C21 H21 0.9300 .
C21 C20 1.388(3) .
C21 C16 1.382(3) .
C11 H11 0.9300 .
C20 H20 0.9300 .
C20 C19 1.380(3) .
C9 H9 0.9300 .
C5 H5 0.9300 .
C18 C19 1.386(3) .
C18 C22 1.504(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 -179.26(16) .
O1 C7 C6 C5 179.41(17) .
C2 C4 C9 C8 -179.50(15) .
C2 C4 C5 C6 179.69(16) .
C2 C10 C15 C14 175.84(15) .
C2 C10 C11 C12 -175.22(16) .
C1 C2 C4 C9 -179.95(14) .
C1 C2 C4 C5 0.1(2) .
C1 C2 C3 C1 56.20(17) 2_566
C1 C2 C10 C15 47.5(2) .
C1 C2 C10 C11 -137.32(16) .
C4 C2 C1 C3 -173.64(12) 2_566
C4 C2 C3 C1 176.02(12) 2_566
C4 C2 C10 C15 -74.38(18) .
C4 C2 C10 C11 100.83(17) .
C3 C2 C1 C3 -55.68(18) 2_566
C3 C2 C4 C9 64.11(19) .
C3 C2 C4 C5 -115.80(17) .
C3 C2 C10 C15 165.75(14) .
C3 C2 C10 C11 -19.0(2) .
C10 C2 C1 C3 67.26(16) 2_566
C10 C2 C4 C9 -58.60(18) .
C10 C2 C4 C5 121.49(17) .
C10 C2 C3 C1 -65.15(17) 2_566
C7 C8 C9 C4 -0.2(3) .
C7 C6 C5 C4 -0.2(3) .
C15 C10 C11 C12 0.2(3) .
C15 C14 C13 O2 -178.07(16) .
C15 C14 C13 C12 0.3(3) .
C17 C18 C19 C20 -0.8(3) .
C8 C7 C6 C5 0.4(3) .
C6 C7 C8 C9 -0.2(3) .
C13 C14 C15 C10 -0.5(3) .
C13 C12 C11 C10 -0.4(3) .
C21 C20 C19 C18 0.4(3) .
C11 C10 C15 C14 0.3(3) .
C11 C12 C13 O2 178.57(16) .
C11 C12 C13 C14 0.2(3) .
C20 C21 C16 O3 179.47(19) .
C20 C21 C16 C17 -0.3(3) .
C9 C4 C5 C6 -0.2(3) .
C16 C17 C18 C19 0.7(3) .
C16 C17 C18 C22 -178.37(19) .
C16 C21 C20 C19 0.1(3) .
C5 C4 C9 C8 0.4(3) .
C18 C17 C16 O3 -179.86(18) .
C18 C17 C16 C21 -0.1(3) .
C22 C18 C19 C20 178.2(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 0.500 172 14 ' '
