#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/04/7220437.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_7220437
loop_
_publ_author_name
'Morohashi, Naoya'
'Nanbu, Kazuki'
'Tonosaki, Ayano'
'Noji, Shintaro'
'Hattori, Tetsutaro'
_publ_section_title
;
 Comparison of inclusion properties between p-tert-butylcalix[4]arene and
 p-tert-butylthiacalix[4]arene towards primary alcohols in crystals
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              4799
_journal_paper_doi               10.1039/C5CE00370A
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C47 H64 O5'
_chemical_formula_weight         708.98
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           85
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4a'
_symmetry_space_group_name_H-M   'P 4/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-23 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.8486(18)
_cell_length_b                   12.8486(18)
_cell_length_c                   12.6773(18)
_cell_measurement_reflns_used    5204
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.26
_cell_volume                     2092.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11340
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1049P)²+1.5925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2109
_reflns_number_gt                1758
_reflns_number_total             2401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00370a2.cif
_cod_data_source_block           1-PrOH
_cod_depositor_comments
'Adding full bibliography for 7220433--7220440.cif.'
_cod_original_sg_symbol_H-M      'P 4/n'
_cod_database_code               7220437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.15896(15) 0.06641(15) 0.46352(16) 0.0170(4) Uani 1 1 d . . .
C2 C 0.23071(15) -0.00240(15) 0.41873(16) 0.0171(4) Uani 1 1 d . . .
C3 C 0.20116(16) -0.05630(15) 0.32882(17) 0.0199(5) Uani 1 1 d . . .
H1 H 0.2480 -0.1031 0.2991 0.024 Uiso 1 1 calc R . .
C4 C 0.10406(16) -0.04338(16) 0.28091(17) 0.0210(5) Uani 1 1 d . . .
C5 C 0.03587(15) 0.02751(15) 0.32743(17) 0.0192(5) Uani 1 1 d . . .
H2 H -0.0290 0.0382 0.2967 0.023 Uiso 1 1 calc R . .
C6 C 0.06152(15) 0.08294(15) 0.41823(16) 0.0169(4) Uani 1 1 d . . .
C7 C 0.07570(18) -0.1083(2) 0.18329(19) 0.0299(6) Uani 1 1 d . . .
C8 C 0.1582(2) -0.0931(3) 0.0976(2) 0.0441(7) Uani 1 1 d . . .
H18 H 0.168(3) -0.012(3) 0.083(3) 0.067(11) Uiso 1 1 d . . .
H8 H 0.228(3) -0.115(2) 0.126(2) 0.045(8) Uiso 1 1 d . . .
C9 C 0.0736(2) -0.2243(2) 0.2147(3) 0.0428(7) Uani 1 1 d . . .
H20 H 0.010(3) -0.229(3) 0.269(3) 0.069(11) Uiso 1 1 d . . .
H9 H 0.056(3) -0.274(3) 0.152(3) 0.060(10) Uiso 1 1 d . . .
C10 C -0.0302(2) -0.0778(3) 0.1380(3) 0.0561(10) Uani 1 1 d . . .
H22 H -0.083(3) -0.099(3) 0.198(3) 0.072(12) Uiso 1 1 d . . .
H10 H -0.028(3) 0.004(3) 0.118(3) 0.070(12) Uiso 1 1 d . . .
C11 C -0.01613(16) 0.16076(16) 0.46387(17) 0.0180(4) Uani 1 1 d . . .
H11 H -0.0124(18) 0.1620(18) 0.541(2) 0.016(6) Uiso 1 1 d . . .
O1 O 0.18768(11) 0.11692(12) 0.55606(11) 0.0206(4) Uani 1 1 d . . .
H14 H 0.154(3) 0.179(3) 0.562(2) 0.046(9) Uiso 1 1 d . . .
H17 H 0.138(3) -0.133(3) 0.035(3) 0.052(9) Uiso 1 1 d . . .
H19 H 0.150(3) -0.249(3) 0.244(3) 0.067(10) Uiso 1 1 d . . .
H21 H -0.044(3) -0.114(3) 0.070(3) 0.065(11) Uiso 1 1 d . . .
H23 H -0.085(2) 0.138(2) 0.445(2) 0.025(6) Uiso 1 1 d . . .
O2A O 0.2500 0.2500 0.2408(8) 0.066(2) Uani 0.50 4 d SPDU A 1
C14B C 0.2500 0.2500 -0.0062(13) 0.076(3) Uani 0.50 4 d SPDU . 2
C14A C 0.2500 0.2500 0.1313(11) 0.095(4) Uani 0.50 4 d SPDU . 1
C12B C 0.2500 0.2500 -0.1275(13) 0.095(5) Uani 0.50 4 d SPDU B 2
C13 C 0.3325(12) 0.2456(14) 0.0557(12) 0.076(3) Uani 0.25 1 d PDU . .
O2C O 0.397(7) 0.321(6) 0.102(6) 0.062(6) Uani 0.0625 1 d PDU . 2
O2B O 0.334(3) 0.250(3) 0.1650(15) 0.068(4) Uani 0.0625 1 d PDU . 2
C12A C 0.399(7) 0.322(6) 0.116(5) 0.077(6) Uani 0.125 1 d PDU . 1
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
O1 C1 C6 120.99(17) . .
O1 C1 C2 117.58(18) . .
C6 C1 C2 121.43(18) . .
C3 C2 C1 117.98(18) . .
C3 C2 C11 120.23(18) . 3
C1 C2 C11 121.76(19) . 3
C2 C3 C4 122.84(18) . .
C2 C3 H1 118.6 . .
C4 C3 H1 118.6 . .
C5 C4 C3 117.04(19) . .
C5 C4 C7 123.10(19) . .
C3 C4 C7 119.83(18) . .
C6 C5 C4 122.32(19) . .
C6 C5 H2 118.8 . .
C4 C5 H2 118.8 . .
C5 C6 C1 118.36(18) . .
C5 C6 C11 119.57(18) . .
C1 C6 C11 122.06(18) . .
C10 C7 C8 108.5(2) . .
C10 C7 C4 112.0(2) . .
C8 C7 C4 109.8(2) . .
C10 C7 C9 109.2(3) . .
C8 C7 C9 108.5(2) . .
C4 C7 C9 108.7(2) . .
C7 C8 H18 109(2) . .
C7 C8 H8 109.5(18) . .
H18 C8 H8 103(3) . .
C7 C8 H17 109(2) . .
H18 C8 H17 113(3) . .
H8 C8 H17 112(3) . .
C7 C9 H20 103(2) . .
C7 C9 H9 113(2) . .
H20 C9 H9 107(3) . .
C7 C9 H19 111(2) . .
H20 C9 H19 117(3) . .
H9 C9 H19 106(3) . .
C7 C10 H22 104(2) . .
C7 C10 H10 108(2) . .
H22 C10 H10 116(3) . .
C7 C10 H21 111(2) . .
H22 C10 H21 113(3) . .
H10 C10 H21 105(3) . .
C2 C11 C6 112.52(16) 4 .
C2 C11 H11 110.8(14) 4 .
C6 C11 H11 110.9(14) . .
C2 C11 H23 106.9(16) 4 .
C6 C11 H23 108.2(16) . .
H11 C11 H23 107(2) . .
C1 O1 H14 111.0(19) . .
C13 C14B C13 69.3(8) 2 4
C13 C14B C13 107.0(17) 2 .
C13 C14B C13 69.3(8) 4 .
C13 C14B C13 69.3(8) 2 3
C13 C14B C13 107.0(17) 4 3
C13 C14B C13 69.3(8) . 3
C13 C14B C12B 126.5(8) 2 .
C13 C14B C12B 126.5(8) 4 .
C13 C14B C12B 126.5(8) . .
C13 C14B C12B 126.5(8) 3 .
O2A C14A C13 132.0(8) . 2
O2A C14A C13 132.0(8) . 4
C13 C14A C13 63.4(8) 2 4
O2A C14A C13 132.0(8) . .
C13 C14A C13 95.9(15) 2 .
C13 C14A C13 63.4(8) 4 .
O2A C14A C13 132.0(8) . 3
C13 C14A C13 63.4(8) 2 3
C13 C14A C13 95.9(15) 4 3
C13 C14A C13 63.4(8) . 3
C14B C13 O2B 127(2) . .
C14B C13 O2C 134(5) . .
O2B C13 O2C 63(4) . .
C14B C13 C14A 78.5(12) . .
O2B C13 C14A 48.8(18) . .
O2C C13 C14A 98(4) . .
C14B C13 C13 55.4(4) . 3
O2B C13 C13 89(2) . 3
O2C C13 C13 83(5) . 3
C14A C13 C13 58.3(4) . 3
C14B C13 C13 55.4(4) . 4
O2B C13 C13 92.4(19) . 4
O2C C13 C13 154(3) . 4
C14A C13 C13 58.3(4) . 4
C13 C13 C13 90.000(2) 3 4
C14B C13 C12A 137(4) . .
O2B C13 C12A 57(3) . .
O2C C13 C12A 6(6) . .
C14A C13 C12A 93(3) . .
C13 C13 C12A 84(4) 3 .
C13 C13 C12A 149(3) 4 .
C14B C13 C12A 102(2) . 4
O2B C13 C12A 70(3) . 4
O2C C13 C12A 121(5) . 4
C14A C13 C12A 74(2) . 4
C13 C13 C12A 130(2) 3 4
C13 C13 C12A 48(2) 4 4
C12A C13 C12A 116(4) . 4
C13 O2B O2B 91.2(19) . 3
C13 O2B O2B 88(2) . 4
O2B O2B O2B 90.000(3) 3 4
C13 C12A C13 48(2) . 3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.391(2) .
C1 C6 1.394(3) .
C1 C2 1.398(3) .
C2 C3 1.387(3) .
C2 C11 1.518(3) 3
C3 C4 1.397(3) .
C3 H1 0.9300 .
C4 C5 1.395(3) .
C4 C7 1.536(3) .
C5 C6 1.393(3) .
C5 H2 0.9300 .
C6 C11 1.526(3) .
C7 C10 1.528(4) .
C7 C8 1.530(4) .
C7 C9 1.544(4) .
C8 H18 1.06(4) .
C8 H8 1.01(3) .
C8 H17 0.98(4) .
C9 H20 1.07(4) .
C9 H9 1.04(4) .
C9 H19 1.10(4) .
C10 H22 1.06(4) .
C10 H10 1.08(4) .
C10 H21 0.99(4) .
C11 C2 1.518(3) 4
C11 H11 0.98(2) .
C11 H23 0.96(3) .
O1 H14 0.91(4) .
O2A C14A 1.389(13) .
C14B C13 1.321(17) 2
C14B C13 1.321(17) 4
C14B C13 1.321(17) .
C14B C13 1.321(17) 3
C14B C12B 1.538(17) .
C14A C13 1.430(14) 2
C14A C13 1.430(14) 4
C14A C13 1.430(14) .
C14A C13 1.430(14) 3
C13 O2B 1.387(14) .
C13 O2C 1.402(15) .
C13 C13 1.50(2) 3
C13 C13 1.50(2) 4
C13 C12A 1.507(19) .
C13 C12A 2.01(8) 4
O2B O2B 1.53(6) 3
O2B O2B 1.53(6) 4
C12A C13 2.01(8) 3
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
O1 C1 C2 C3 177.44(17) . .
C6 C1 C2 C3 -1.6(3) . .
O1 C1 C2 C11 -4.5(3) . 3
C6 C1 C2 C11 176.37(18) . 3
C1 C2 C3 C4 1.0(3) . .
C11 C2 C3 C4 -177.05(18) 3 .
C2 C3 C4 C5 0.1(3) . .
C2 C3 C4 C7 -178.19(19) . .
C3 C4 C5 C6 -0.7(3) . .
C7 C4 C5 C6 177.6(2) . .
C4 C5 C6 C1 0.0(3) . .
C4 C5 C6 C11 178.92(18) . .
O1 C1 C6 C5 -177.90(17) . .
C2 C1 C6 C5 1.2(3) . .
O1 C1 C6 C11 3.2(3) . .
C2 C1 C6 C11 -177.71(18) . .
C5 C4 C7 C10 5.7(4) . .
C3 C4 C7 C10 -176.1(3) . .
C5 C4 C7 C8 126.4(2) . .
C3 C4 C7 C8 -55.4(3) . .
C5 C4 C7 C9 -115.0(2) . .
C3 C4 C7 C9 63.2(3) . .
C5 C6 C11 C2 -89.8(2) . 4
C1 C6 C11 C2 89.1(2) . 4
C13 C14B C13 O2B -3(2) 2 .
C13 C14B C13 O2B -63(2) 4 .
C13 C14B C13 O2B 56(3) 3 .
C12B C14B C13 O2B 177(2) . .
C13 C14B C13 O2C -89(5) 2 .
C13 C14B C13 O2C -149(5) 4 .
C13 C14B C13 O2C -30(5) 3 .
C12B C14B C13 O2C 91(5) . .
C13 C14B C13 C14A 0.0 2 .
C13 C14B C13 C14A -59.3(5) 4 .
C13 C14B C13 C14A 59.3(5) 3 .
C12B C14B C13 C14A 180.0 . .
C13 C14B C13 C13 -59.3(5) 2 3
C13 C14B C13 C13 -118.5(10) 4 3
C12B C14B C13 C13 120.7(5) . 3
C13 C14B C13 C13 59.3(5) 2 4
C13 C14B C13 C13 118.5(10) 3 4
C12B C14B C13 C13 -120.7(5) . 4
C13 C14B C13 C12A -82(5) 2 .
C13 C14B C13 C12A -141(5) 4 .
C13 C14B C13 C12A -23(5) 3 .
C12B C14B C13 C12A 98(5) . .
C13 C14B C13 C12A 71(2) 2 4
C13 C14B C13 C12A 12(2) 4 4
C13 C14B C13 C12A 130(2) 3 4
C12B C14B C13 C12A -109(2) . 4
O2A C14A C13 C14B 180.0 . .
C13 C14A C13 C14B 0.0 2 .
C13 C14A C13 C14B 56.2(4) 4 .
C13 C14A C13 C14B -56.2(4) 3 .
O2A C14A C13 O2B -3(3) . .
C13 C14A C13 O2B 177(3) 2 .
C13 C14A C13 O2B -127(3) 4 .
C13 C14A C13 O2B 120(3) 3 .
O2A C14A C13 O2C -47(5) . .
C13 C14A C13 O2C 133(5) 2 .
C13 C14A C13 O2C -170(5) 4 .
C13 C14A C13 O2C 77(5) 3 .
O2A C14A C13 C13 -123.8(4) . 3
C13 C14A C13 C13 56.2(4) 2 3
C13 C14A C13 C13 112.4(8) 4 3
O2A C14A C13 C13 123.8(4) . 4
C13 C14A C13 C13 -56.2(4) 2 4
C13 C14A C13 C13 -112.4(8) 3 4
O2A C14A C13 C12A -43(4) . .
C13 C14A C13 C12A 137(4) 2 .
C13 C14A C13 C12A -167(4) 4 .
C13 C14A C13 C12A 81(4) 3 .
O2A C14A C13 C12A 74(2) . 4
C13 C14A C13 C12A -106(2) 2 4
C13 C14A C13 C12A -50(2) 4 4
C13 C14A C13 C12A -163(2) 3 4
C14B C13 O2B O2B -40(4) . 3
O2C C13 O2B O2B 86(6) . 3
C14A C13 O2B O2B -43.9(8) . 3
C13 C13 O2B O2B 3(3) 3 3
C13 C13 O2B O2B -87(3) 4 3
C12A C13 O2B O2B 87(6) . 3
C12A C13 O2B O2B -130(3) 4 3
C14B C13 O2B O2B 50(4) . 4
O2C C13 O2B O2B 176(6) . 4
C14A C13 O2B O2B 46.0(7) . 4
C13 C13 O2B O2B 93(2) 3 4
C13 C13 O2B O2B 3(3) 4 4
C12A C13 O2B O2B 177(6) . 4
C12A C13 O2B O2B -40(3) 4 4
C14B C13 C12A C13 19(4) . 3
O2B C13 C12A C13 -92(3) . 3
O2C C13 C12A C13 84(83) . 3
C14A C13 C12A C13 -57.7(7) . 3
C13 C13 C12A C13 -80(7) 4 3
C12A C13 C12A C13 -132(3) 4 3
