#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:45:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178442 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/63/4026329.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_4026329
loop_
_publ_author_name
'Lev Kuno'
'Silvio E. Biali'
_publ_section_title
;
 Calix[4]arenes with Two Different Chemical Modifications at the Bridges
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3664
_journal_page_last               3675
_journal_paper_doi               10.1021/jo200580m
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C64 H76 O6'
_chemical_formula_sum            'C64 H76 O6'
_chemical_formula_weight         941.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 96.792(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9296(11)
_cell_length_b                   20.074(2)
_cell_length_c                   28.271(3)
_cell_measurement_temperature    173(1)
_cell_volume                     5595.6(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            31758
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       shapeless
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0735P)²+3.5656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1632
_reflns_number_gt                5571
_reflns_number_total             6692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200580m_si_005.cif
_cod_data_source_block           lev101m
_cod_original_cell_volume        5595.8(11)
_cod_database_code               4026329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C1 C 0.40307(16) 0.50096(8) 0.19702(5) 0.0249(3) Uani 1 1 d .
C2 C 0.47666(16) 0.55998(8) 0.20347(5) 0.0240(3) Uani 1 1 d .
C3 C 0.53442(16) 0.58749(8) 0.16502(5) 0.0234(3) Uani 1 1 d .
H3 H 0.5834 0.6281 0.1695 0.028 Uiso 1 1 calc R
C4 C 0.52228(15) 0.55734(8) 0.12057(5) 0.0222(3) Uani 1 1 d .
C5 C 0.44479(15) 0.49907(8) 0.11516(5) 0.0234(3) Uani 1 1 d .
H5 H 0.4314 0.4785 0.0847 0.028 Uiso 1 1 calc R
C6 C 0.38643(15) 0.46992(8) 0.15246(5) 0.0229(3) Uani 1 1 d .
C7 C 0.31311(15) 0.40297(8) 0.14698(6) 0.0240(3) Uani 1 1 d .
H7 H 0.2512 0.4011 0.1724 0.029 Uiso 1 1 calc R
C8 C 0.40365(16) 0.30245(8) 0.19452(6) 0.0246(3) Uani 1 1 d .
C9 C 0.41719(15) 0.34762(8) 0.15795(5) 0.0236(3) Uani 1 1 d .
C10 C 0.53194(16) 0.34217(8) 0.13420(6) 0.0276(3) Uani 1 1 d .
H10 H 0.5444 0.3741 0.1103 0.033 Uiso 1 1 calc R
C11 C 0.62948(16) 0.29244(8) 0.14363(6) 0.0273(3) Uani 1 1 d .
C12 C 0.60935(17) 0.24653(8) 0.17905(6) 0.0291(4) Uani 1 1 d .
H12 H 0.6710 0.2105 0.1852 0.035 Uiso 1 1 calc R
C13 C 0.50029(17) 0.25254(8) 0.20551(6) 0.0265(3) Uani 1 1 d .
C14 C 0.5000 0.21155(11) 0.2500 0.0295(5) Uani 1 2 d S
C15 C 0.5000 0.59677(11) 0.2500 0.0253(5) Uani 1 2 d S
C16 C 0.2344(2) 0.50186(15) 0.25070(8) 0.0602(7) Uani 1 1 d .
H16A H 0.2406 0.5502 0.2466 0.090 Uiso 1 1 calc R
H16B H 0.2322 0.4915 0.2845 0.090 Uiso 1 1 calc R
H16C H 0.1515 0.4853 0.2322 0.090 Uiso 1 1 calc R
C17 C 0.59381(17) 0.58363(8) 0.07893(6) 0.0274(3) Uani 1 1 d .
C18 C 0.6843(2) 0.64364(9) 0.09305(7) 0.0376(4) Uani 1 1 d .
H18A H 0.7287 0.6581 0.0656 0.056 Uiso 1 1 calc R
H18B H 0.7533 0.6312 0.1192 0.056 Uiso 1 1 calc R
H18C H 0.6289 0.6801 0.1033 0.056 Uiso 1 1 calc R
C19 C 0.4881(2) 0.60356(11) 0.03734(6) 0.0420(5) Uani 1 1 d .
H19A H 0.4333 0.6406 0.0471 0.063 Uiso 1 1 calc R
H19B H 0.4292 0.5654 0.0281 0.063 Uiso 1 1 calc R
H19C H 0.5344 0.6174 0.0102 0.063 Uiso 1 1 calc R
C20 C 0.6840(2) 0.52794(10) 0.06233(7) 0.0413(5) Uani 1 1 d .
H20A H 0.7315 0.5444 0.0362 0.062 Uiso 1 1 calc R
H20B H 0.6274 0.4897 0.0513 0.062 Uiso 1 1 calc R
H20C H 0.7505 0.5142 0.0889 0.062 Uiso 1 1 calc R
C21 C 0.22371(16) 0.39463(8) 0.09936(6) 0.0269(3) Uani 1 1 d .
C22 C 0.11511(17) 0.43917(9) 0.08739(7) 0.0333(4) Uani 1 1 d .
C23 C 0.03198(19) 0.42987(10) 0.04477(7) 0.0397(4) Uani 1 1 d .
H23 H -0.0395 0.4607 0.0364 0.048 Uiso 1 1 calc R
C24 C 0.04882(19) 0.37763(10) 0.01392(7) 0.0401(5) Uani 1 1 d .
C25 C 0.1530(2) 0.33345(10) 0.02692(7) 0.0399(4) Uani 1 1 d .
H25 H 0.1656 0.2965 0.0069 0.048 Uiso 1 1 calc R
C26 C 0.23959(18) 0.34204(9) 0.06866(6) 0.0336(4) Uani 1 1 d .
H26 H 0.3114 0.3112 0.0764 0.040 Uiso 1 1 calc R
C27 C 0.0821(2) 0.49373(10) 0.12084(8) 0.0465(5) Uani 1 1 d .
H27A H -0.0037 0.5149 0.1083 0.070 Uiso 1 1 calc R
H27B H 0.1548 0.5270 0.1237 0.070 Uiso 1 1 calc R
H27C H 0.0737 0.4747 0.1523 0.070 Uiso 1 1 calc R
C28 C -0.0465(2) 0.36891(14) -0.03125(8) 0.0592(6) Uani 1 1 d .
H28A H -0.1249 0.3424 -0.0246 0.089 Uiso 1 1 calc R
H28B H 0.0008 0.3460 -0.0551 0.089 Uiso 1 1 calc R
H28C H -0.0774 0.4127 -0.0435 0.089 Uiso 1 1 calc R
C29 C 0.1897(2) 0.26218(12) 0.20865(9) 0.0527(6) Uani 1 1 d .
H29A H 0.1502 0.2700 0.1757 0.079 Uiso 1 1 calc R
H29B H 0.1197 0.2679 0.2300 0.079 Uiso 1 1 calc R
H29C H 0.2258 0.2168 0.2117 0.079 Uiso 1 1 calc R
C30 C 0.76022(18) 0.29420(9) 0.11978(6) 0.0341(4) Uani 1 1 d .
C31 C 0.7309(2) 0.30957(12) 0.06644(7) 0.0482(5) Uani 1 1 d .
H31A H 0.6673 0.2765 0.0512 0.072 Uiso 1 1 calc R
H31B H 0.8157 0.3079 0.0519 0.072 Uiso 1 1 calc R
H31C H 0.6910 0.3541 0.0621 0.072 Uiso 1 1 calc R
C32 C 0.8503(2) 0.34950(12) 0.14371(9) 0.0506(5) Uani 1 1 d .
H32A H 0.8031 0.3923 0.1392 0.076 Uiso 1 1 calc R
H32B H 0.9353 0.3515 0.1294 0.076 Uiso 1 1 calc R
H32C H 0.8701 0.3401 0.1778 0.076 Uiso 1 1 calc R
C33 C 0.8368(2) 0.22817(11) 0.12572(9) 0.0516(6) Uani 1 1 d .
H33A H 0.8646 0.2199 0.1596 0.077 Uiso 1 1 calc R
H33B H 0.9173 0.2303 0.1088 0.077 Uiso 1 1 calc R
H33C H 0.7776 0.1920 0.1125 0.077 Uiso 1 1 calc R
O1 O 0.34999(14) 0.47054(6) 0.23433(4) 0.0384(3) Uani 1 1 d .
O2 O 0.29606(11) 0.30844(6) 0.22105(4) 0.0296(3) Uani 1 1 d .
O3 O 0.5000 0.15113(9) 0.2500 0.0509(5) Uani 1 2 d S
O4 O 0.5000 0.65735(8) 0.2500 0.0371(4) Uani 1 2 d S
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 C2 121.31(14) . .
O1 C1 C6 118.54(14) . .
C2 C1 C6 120.10(14) . .
C1 C2 C3 119.36(14) . .
C1 C2 C15 123.85(13) . .
C3 C2 C15 116.78(14) . .
C4 C3 C2 122.09(14) . .
C4 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
C3 C4 C5 116.85(13) . .
C3 C4 C17 123.03(14) . .
C5 C4 C17 120.07(13) . .
C6 C5 C4 122.84(14) . .
C6 C5 H5 118.6 . .
C4 C5 H5 118.6 . .
C5 C6 C1 118.70(14) . .
C5 C6 C7 121.98(13) . .
C1 C6 C7 119.19(13) . .
C9 C7 C6 108.49(12) . .
C9 C7 C21 114.06(13) . .
C6 C7 C21 113.89(13) . .
C9 C7 H7 106.6 . .
C6 C7 H7 106.6 . .
C21 C7 H7 106.6 . .
O2 C8 C9 119.67(14) . .
O2 C8 C13 119.79(14) . .
C9 C8 C13 120.52(14) . .
C8 C9 C10 117.55(14) . .
C8 C9 C7 120.18(14) . .
C10 C9 C7 122.18(14) . .
C9 C10 C11 123.57(15) . .
C9 C10 H10 118.2 . .
C11 C10 H10 118.2 . .
C12 C11 C10 117.12(15) . .
C12 C11 C30 122.19(15) . .
C10 C11 C30 120.31(15) . .
C13 C12 C11 121.05(15) . .
C13 C12 H12 119.5 . .
C11 C12 H12 119.5 . .
C12 C13 C8 120.01(15) . .
C12 C13 C14 118.73(14) . .
C8 C13 C14 120.63(13) . .
O3 C14 C13 123.18(9) . 2_655
O3 C14 C13 123.18(9) . .
C13 C14 C13 113.63(19) 2_655 .
O4 C15 C2 119.44(9) . .
O4 C15 C2 119.44(9) . 2_655
C2 C15 C2 121.12(18) . 2_655
O1 C16 H16A 109.5 . .
O1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 C19 108.82(15) . .
C18 C17 C4 112.40(13) . .
C19 C17 C4 109.89(14) . .
C18 C17 C20 107.89(15) . .
C19 C17 C20 108.99(15) . .
C4 C17 C20 108.77(13) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 C20 H20A 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C17 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C26 C21 C22 118.18(15) . .
C26 C21 C7 122.41(15) . .
C22 C21 C7 119.26(15) . .
C23 C22 C21 118.79(17) . .
C23 C22 C27 119.35(17) . .
C21 C22 C27 121.76(16) . .
C24 C23 C22 122.91(18) . .
C24 C23 H23 118.5 . .
C22 C23 H23 118.5 . .
C25 C24 C23 117.46(17) . .
C25 C24 C28 121.8(2) . .
C23 C24 C28 120.7(2) . .
C24 C25 C26 121.14(18) . .
C24 C25 H25 119.4 . .
C26 C25 H25 119.4 . .
C25 C26 C21 121.48(17) . .
C25 C26 H26 119.3 . .
C21 C26 H26 119.3 . .
C22 C27 H27A 109.5 . .
C22 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C22 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C24 C28 H28A 109.5 . .
C24 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C24 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O2 C29 H29A 109.5 . .
O2 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
O2 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C33 C30 C32 108.86(17) . .
C33 C30 C11 111.61(15) . .
C32 C30 C11 107.65(15) . .
C33 C30 C31 108.47(16) . .
C32 C30 C31 108.76(17) . .
C11 C30 C31 111.43(15) . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C30 C32 H32A 109.5 . .
C30 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C30 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C30 C33 H33A 109.5 . .
C30 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
C30 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C1 O1 C16 116.54(16) . .
C8 O2 C29 114.19(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.3765(19) .
C1 C2 1.393(2) .
C1 C6 1.398(2) .
C2 C3 1.401(2) .
C2 C15 1.5024(18) .
C3 C4 1.387(2) .
C3 H3 0.9500 .
C4 C5 1.398(2) .
C4 C17 1.538(2) .
C5 C6 1.391(2) .
C5 H5 0.9500 .
C6 C7 1.528(2) .
C7 C9 1.524(2) .
C7 C21 1.532(2) .
C7 H7 1.0000 .
C8 O2 1.3812(19) .
C8 C9 1.394(2) .
C8 C13 1.397(2) .
C9 C10 1.394(2) .
C10 C11 1.395(2) .
C10 H10 0.9500 .
C11 C12 1.393(2) .
C11 C30 1.532(2) .
C12 C13 1.392(2) .
C12 H12 0.9500 .
C13 C14 1.503(2) .
C14 O3 1.213(3) .
C14 C13 1.503(2) 2_655
C15 O4 1.216(3) .
C15 C2 1.5024(18) 2_655
C16 O1 1.432(3) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.527(2) .
C17 C19 1.533(3) .
C17 C20 1.540(2) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C26 1.388(2) .
C21 C22 1.411(2) .
C22 C23 1.390(3) .
C22 C27 1.508(3) .
C23 C24 1.387(3) .
C23 H23 0.9500 .
C24 C25 1.379(3) .
C24 C28 1.507(3) .
C25 C26 1.386(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 O2 1.419(2) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 C33 1.527(3) .
C30 C32 1.532(3) .
C30 C31 1.533(3) .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
