#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/33/1513377.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_1513377
loop_
_publ_author_name
'Surov, Oleg V.'
'Voronova, Marina I.'
'Barannikov, Vladimir P.'
'Shaposhnikov, Gennady P.'
_publ_section_title
;
 Structural Features and Thermal Stability of
 25,26,27,28-Tetrahydroxycalix[4]arene Molecular Complexes with Solvents
;
_journal_issue                   1
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              338
_journal_paper_doi               10.1021/jp409003f
_journal_volume                  118
_journal_year                    2014
_chemical_formula_moiety         'C28 H20 O4'
_chemical_formula_sum            'C28 H20 O4'
_chemical_formula_weight         420.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           176
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 6c'
_symmetry_space_group_name_H-M   'P 63/m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   14.7660(17)
_cell_length_b                   14.7660(17)
_cell_length_c                   17.858(4)
_cell_measurement_reflns_used    1563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.34
_cell_volume                     3372.0(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2492
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_platon_squeeze_details
;
;
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0569
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                1693
_reflns_number_total             2492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp409003f_si_001.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P63/m
_cod_database_code               1513377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
'-x, -y, -z'
'-x+y, -x, -z-1/2'
'y, -x+y, -z'
'x, y, -z-1/2'
'x-y, x, -z'
'-y, x-y, -z-1/2'
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
O1 O 0.00964(18) 0.16383(16) 0.2500 0.0749(8) Uani 1 2 d S
O2 O -0.00610(11) 0.29080(11) 0.34668(9) 0.0580(4) Uani 1 1 d .
O3 O -0.04689(14) 0.39885(15) 0.2500 0.0512(6) Uani 1 2 d S
C1 C 0.1157(3) 0.1945(2) 0.2500 0.0618(10) Uani 1 2 d S
C2 C 0.1655(2) 0.20783(16) 0.31862(17) 0.0636(7) Uani 1 1 d .
C3 C 0.2710(2) 0.23751(17) 0.31663(17) 0.0720(8) Uani 1 1 d .
H3A H 0.3072 0.2474 0.3613 0.086 Uiso 1 1 calc R
C4 C 0.3223(3) 0.2523(3) 0.2500 0.0759(12) Uani 1 2 d S
H4A H 0.3930 0.2727 0.2500 0.091 Uiso 1 2 calc SR
C5 C 0.1103(2) 0.19398(17) 0.39277(16) 0.0732(8) Uani 1 1 d .
H5A H 0.0358 0.1475 0.3857 0.088 Uiso 1 1 calc R
H5B H 0.1348 0.1610 0.4280 0.088 Uiso 1 1 calc R
C6 C 0.12792(19) 0.29595(18) 0.42579(14) 0.0585(7) Uani 1 1 d .
C7 C 0.2002(2) 0.3458(2) 0.48200(14) 0.0635(7) Uani 1 1 d .
H7A H 0.2369 0.3148 0.5009 0.076 Uiso 1 1 calc R
C8 C 0.21933(18) 0.4399(2) 0.51087(14) 0.0640(7) Uani 1 1 d .
H8A H 0.2671 0.4712 0.5497 0.077 Uiso 1 1 calc R
C9 C 0.16711(18) 0.48797(19) 0.48189(12) 0.0558(6) Uani 1 1 d .
H9A H 0.1816 0.5527 0.5004 0.067 Uiso 1 1 calc R
C10 C 0.09273(16) 0.44041(18) 0.42509(12) 0.0469(6) Uani 1 1 d .
C11 C 0.07216(17) 0.34339(18) 0.39898(12) 0.0515(6) Uani 1 1 d .
C12 C 0.03698(16) 0.49450(17) 0.39299(11) 0.0476(6) Uani 1 1 d .
H12A H 0.0415 0.5460 0.4288 0.057 Uiso 1 1 calc R
H12B H -0.0364 0.4431 0.3866 0.057 Uiso 1 1 calc R
C13 C 0.0395(2) 0.5001(2) 0.2500 0.0384(7) Uani 1 2 d S
C14 C 0.08051(15) 0.54841(15) 0.31844(11) 0.0377(5) Uani 1 1 d .
C15 C 0.16545(15) 0.64912(15) 0.31691(11) 0.0405(5) Uani 1 1 d .
H15A H 0.1946 0.6835 0.3617 0.049 Uiso 1 1 calc R
C16 C 0.2073(2) 0.6989(2) 0.2500 0.0422(7) Uani 1 2 d S
H16A H 0.2642 0.7666 0.2500 0.051 Uiso 1 2 calc SR
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
_geom_angle_site_symmetry_3
C2 C1 C2 123.5(4) . 10_556
C2 C1 O1 118.27(19) . .
C2 C1 O1 118.27(19) 10_556 .
C1 C2 C3 116.8(3) . .
C1 C2 C5 122.7(2) . .
C3 C2 C5 120.5(3) . .
C4 C3 C2 121.0(3) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C3 C4 C3 120.9(4) 10_556 .
C3 C4 H4A 119.6 10_556 .
C3 C4 H4A 119.6 . .
C6 C5 C2 113.15(19) . .
C6 C5 H5A 108.9 . .
C2 C5 H5A 108.9 . .
C6 C5 H5B 108.9 . .
C2 C5 H5B 108.9 . .
H5A C5 H5B 107.8 . .
C7 C6 C11 118.1(2) . .
C7 C6 C5 121.1(2) . .
C11 C6 C5 120.7(2) . .
C8 C7 C6 121.8(2) . .
C8 C7 H7A 119.1 . .
C6 C7 H7A 119.1 . .
C7 C8 C9 119.6(2) . .
C7 C8 H8A 120.2 . .
C9 C8 H8A 120.2 . .
C8 C9 C10 120.9(2) . .
C8 C9 H9A 119.6 . .
C10 C9 H9A 119.6 . .
C11 C10 C9 118.2(2) . .
C11 C10 C12 121.3(2) . .
C9 C10 C12 120.4(2) . .
O2 C11 C10 119.8(2) . .
O2 C11 C6 118.9(2) . .
C10 C11 C6 121.3(2) . .
C10 C12 C14 114.09(16) . .
C10 C12 H12A 108.7 . .
C14 C12 H12A 108.7 . .
C10 C12 H12B 108.7 . .
C14 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C14 C13 C14 122.8(3) . 10_556
C14 C13 O3 118.58(13) . .
C14 C13 O3 118.58(13) 10_556 .
C15 C14 C13 117.5(2) . .
C15 C14 C12 119.89(18) . .
C13 C14 C12 122.64(18) . .
C16 C15 C14 120.9(2) . .
C16 C15 H15A 119.5 . .
C14 C15 H15A 119.5 . .
C15 C16 C15 120.4(3) 10_556 .
C15 C16 H16A 119.8 10_556 .
C15 C16 H16A 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.396(4) .
O2 C11 1.383(2) .
O3 C13 1.398(3) .
C1 C2 1.391(3) .
C1 C2 1.391(3) 10_556
C2 C3 1.392(3) .
C2 C5 1.515(3) .
C3 C4 1.368(3) .
C3 H3A 0.9300 .
C4 C3 1.368(3) 10_556
C4 H4A 0.9300 .
C5 C6 1.513(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.379(3) .
C6 C11 1.405(3) .
C7 C8 1.373(3) .
C7 H7A 0.9300 .
C8 C9 1.383(3) .
C8 H8A 0.9300 .
C9 C10 1.399(3) .
C9 H9A 0.9300 .
C10 C11 1.388(3) .
C10 C12 1.517(3) .
C12 C14 1.519(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.392(2) .
C13 C14 1.392(2) 10_556
C14 C15 1.386(3) .
C15 C16 1.377(2) .
C15 H15A 0.9300 .
C16 C15 1.377(2) 10_556
C16 H16A 0.9300 .
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_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 0.9(5) 10_556 .
O1 C1 C2 C3 179.4(2) . .
C2 C1 C2 C5 179.40(19) 10_556 .
O1 C1 C2 C5 -2.1(4) . .
C1 C2 C3 C4 -0.2(4) . .
C5 C2 C3 C4 -178.7(3) . .
C2 C3 C4 C3 -0.6(5) . 10_556
C1 C2 C5 C6 -96.5(3) . .
C3 C2 C5 C6 81.9(3) . .
C2 C5 C6 C7 -100.3(3) . .
C2 C5 C6 C11 78.6(3) . .
C11 C6 C7 C8 -1.0(3) . .
C5 C6 C7 C8 177.9(2) . .
C6 C7 C8 C9 -1.7(4) . .
C7 C8 C9 C10 1.9(3) . .
C8 C9 C10 C11 0.5(3) . .
C8 C9 C10 C12 -179.18(19) . .
C9 C10 C11 O2 175.43(17) . .
C12 C10 C11 O2 -4.9(3) . .
C9 C10 C11 C6 -3.2(3) . .
C12 C10 C11 C6 176.43(19) . .
C7 C6 C11 O2 -175.17(19) . .
C5 C6 C11 O2 5.9(3) . .
C7 C6 C11 C10 3.5(3) . .
C5 C6 C11 C10 -175.5(2) . .
C11 C10 C12 C14 -79.0(3) . .
C9 C10 C12 C14 100.7(2) . .
C14 C13 C14 C15 0.4(4) 10_556 .
O3 C13 C14 C15 -179.38(19) . .
C14 C13 C14 C12 -178.62(16) 10_556 .
O3 C13 C14 C12 1.6(3) . .
C10 C12 C14 C15 -85.0(2) . .
C10 C12 C14 C13 94.0(3) . .
C13 C14 C15 C16 -0.1(3) . .
C12 C14 C15 C16 179.0(2) . .
C14 C15 C16 C15 -0.2(4) . 10_556
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 0.000 0.000 0.000 8 0 ' '
2 0.000 0.000 0.500 8 0 ' '
3 0.333 0.667 0.250 149 46 ' '
4 0.667 0.333 0.750 149 46 ' '
