#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/70/1507045.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_1507045
loop_
_publ_author_name
'Higham, Luke T.'
'Kreher, Ulf P.'
'Raston, Colin L.'
'Scott, Janet L.'
'Strauss, Christopher R.'
_publ_section_title
;
 Horning-crown macrocycles: novel hybrids of calixarenes and crown ethers.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              3261
_journal_page_last               3264
_journal_paper_doi               10.1021/ol048921s
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C44 H40 O6 . 2(C9 H13 N)'
_chemical_formula_sum            'C62 H66 N2 O6'
_chemical_formula_weight         935.17
_chemical_name_systematic
; 
3,4:9,10:18,19:24,25-Tetrabenzo-5,8,20,23-tetraoxa-tricyclo[25.3.1.112,16]dotriaconta-1(30),3,9,12,14,16(32),18,24,27(31),28-decaene-31,32-diol phenylisopropylamine inclusion complex
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                98.4710(10)
_cell_angle_beta                 107.0440(10)
_cell_angle_gamma                110.4740(10)
_cell_formula_units_Z            1
_cell_length_a                   9.2697(3)
_cell_length_b                   12.5253(3)
_cell_length_c                   12.7887(4)
_cell_measurement_temperature    123(2)
_cell_volume                     1277.17(7)
_computing_cell_refinement       'Nonius collect'
_computing_data_collection       'Nonius collect'
_computing_data_reduction        'Nonius collect'
_computing_molecular_graphics    X-Seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Enraf Nonius Kappa CCD'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4653
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.222
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0737
_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)+(0.1137P)²+0.8918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1951
_refine_ls_wR_factor_ref         0.2205
_reflns_number_gt                3158
_reflns_number_total             4653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048921ssi20040809_091408.cif
_cod_data_source_block           4.phenylisopropylamine
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
O3 O 0.1955(3) 0.70590(18) 0.78597(16) 0.0399(5) Uani 1 1 d .
O2 O -0.0363(2) 0.53623(17) 1.36428(17) 0.0388(5) Uani 1 1 d .
O1 O 0.1671(3) 0.64943(18) 1.1393(2) 0.0451(6) Uani 1 1 d .
C2 C 0.3989(3) 0.8205(2) 1.1444(2) 0.0328(7) Uani 1 1 d .
C1 C 0.3043(3) 0.7529(2) 1.1977(2) 0.0315(6) Uani 1 1 d .
C5 C 0.4930(3) 0.8905(2) 1.3799(2) 0.0332(7) Uani 1 1 d .
H5 H 0.5267 0.9142 1.4604 0.040 Uiso 1 1 calc R
C6 C 0.3512(3) 0.7874(2) 1.3168(2) 0.0302(6) Uani 1 1 d .
C22 C -0.0444(4) 0.6441(3) 1.3686(2) 0.0358(7) Uani 1 1 d .
C21 C 0.0980(4) 0.7360(3) 1.3723(2) 0.0324(7) Uani 1 1 d .
C8 C 0.2485(4) 0.7129(3) 1.3730(3) 0.0361(7) Uani 1 1 d .
H8A H 0.3200 0.7277 1.4530 0.043 Uiso 1 1 calc R
H8B H 0.2106 0.6281 1.3340 0.043 Uiso 1 1 calc R
C4 C 0.5860(3) 0.9592(3) 1.3281(2) 0.0360(7) Uani 1 1 d .
H4 H 0.6814 1.0303 1.3724 0.043 Uiso 1 1 calc R
C3 C 0.5388(3) 0.9235(3) 1.2113(3) 0.0359(7) Uani 1 1 d .
H3 H 0.6035 0.9704 1.1758 0.043 Uiso 1 1 calc R
C9 C -0.1759(4) 0.4392(3) 1.3632(2) 0.0387(7) Uani 1 1 d .
H9A H -0.2792 0.4324 1.3053 0.046 Uiso 1 1 calc R
H9B H -0.1858 0.4512 1.4386 0.046 Uiso 1 1 calc R
C12 C 0.1740(3) 0.8020(2) 0.8330(2) 0.0345(7) Uani 1 1 d .
C7 C 0.3516(4) 0.7851(3) 1.0167(2) 0.0377(7) Uani 1 1 d .
H7A H 0.2869 0.6980 0.9873 0.045 Uiso 1 1 calc R
H7B H 0.4542 0.8046 1.0002 0.045 Uiso 1 1 calc R
N1G N -0.0755(3) 0.6159(3) 0.9481(2) 0.0470(7) Uani 1 1 d .
C11 C 0.2512(3) 0.8440(2) 0.9530(2) 0.0339(7) Uani 1 1 d .
C26 C 0.0961(4) 0.8464(3) 1.3767(3) 0.0433(8) Uani 1 1 d .
H26 H 0.1917 0.9102 1.3794 0.052 Uiso 1 1 calc R
C10 C 0.1482(4) 0.6708(3) 0.6651(2) 0.0402(7) Uani 1 1 d .
H10A H 0.2166 0.7344 0.6400 0.048 Uiso 1 1 calc R
H10B H 0.0301 0.6543 0.6266 0.048 Uiso 1 1 calc R
C13 C 0.0814(4) 0.8537(3) 0.7723(3) 0.0415(8) Uani 1 1 d .
H13 H 0.0283 0.8236 0.6918 0.050 Uiso 1 1 calc R
C16 C 0.2326(4) 0.9406(3) 1.0060(3) 0.0414(7) Uani 1 1 d .
H16 H 0.2837 0.9711 1.0866 0.050 Uiso 1 1 calc R
C15 C 0.1424(4) 0.9935(3) 0.9456(3) 0.0478(8) Uani 1 1 d .
H15 H 0.1329 1.0601 0.9843 0.057 Uiso 1 1 calc R
C1G C -0.3718(4) 0.6371(4) 0.7831(3) 0.0592(11) Uani 1 1 d .
C14 C 0.0664(4) 0.9500(3) 0.8295(3) 0.0485(8) Uani 1 1 d .
H14 H 0.0031 0.9860 0.7879 0.058 Uiso 1 1 calc R
C23 C -0.1848(4) 0.6624(3) 1.3675(3) 0.0525(9) Uani 1 1 d .
H23 H -0.2810 0.5990 1.3645 0.063 Uiso 1 1 calc R
C6G C -0.3481(4) 0.5858(4) 0.6908(3) 0.0591(10) Uani 1 1 d .
H6G H -0.3350 0.5136 0.6875 0.071 Uiso 1 1 calc R
C25 C -0.0421(5) 0.8667(3) 1.3772(3) 0.0558(10) Uani 1 1 d .
H25 H -0.0398 0.9437 1.3817 0.067 Uiso 1 1 calc R
C24 C -0.1824(5) 0.7739(4) 1.3709(4) 0.0613(10) Uani 1 1 d .
H24 H -0.2782 0.7867 1.3690 0.074 Uiso 1 1 calc R
C2G C -0.3906(4) 0.7487(4) 0.7790(4) 0.0821(17) Uani 1 1 d .
H2G H -0.4078 0.7897 0.8396 0.099 Uiso 1 1 calc R
C4G C -0.3605(5) 0.7389(5) 0.6036(5) 0.0862(15) Uani 1 1 d .
H4G H -0.3561 0.7713 0.5414 0.103 Uiso 1 1 calc R
C7G C -0.3755(5) 0.5853(5) 0.8795(4) 0.0847(15) Uani 1 1 d .
H7G1 H -0.4150 0.4983 0.8510 0.102 Uiso 1 1 calc R
H7G2 H -0.4573 0.6000 0.9079 0.102 Uiso 1 1 calc R
C5G C -0.3428(5) 0.6369(5) 0.6027(4) 0.0759(13) Uani 1 1 d .
H5G H -0.3262 0.5991 0.5400 0.091 Uiso 1 1 calc R
C8G C -0.2082(5) 0.6334(5) 0.9802(3) 0.0819(15) Uani 1 1 d .
H8G H -0.1718 0.7214 1.0021 0.098 Uiso 1 1 calc R
C3G C -0.3835(5) 0.7946(5) 0.6871(5) 0.0793(14) Uani 1 1 d .
H3G H -0.3954 0.8667 0.6853 0.095 Uiso 1 1 calc R
C9G C -0.2292(8) 0.5999(8) 1.0745(5) 0.131(3) Uani 1 1 d .
H9G1 H -0.1224 0.6362 1.1387 0.196 Uiso 1 1 calc R
H9G2 H -0.2720 0.5133 1.0577 0.196 Uiso 1 1 calc R
H9G3 H -0.3082 0.6263 1.0941 0.196 Uiso 1 1 calc R
H1NB H -0.052(5) 0.659(4) 0.893(4) 0.067(12) Uiso 1 1 d .
H1NA H -0.109(5) 0.542(4) 0.912(3) 0.060(11) Uiso 1 1 d .
H1O H 0.098(6) 0.651(4) 1.077(4) 0.086(15) Uiso 1 1 d .
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'
N N 0.0061 0.0033 '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_3
C12 O3 C10 118.0(2) .
C22 O2 C9 118.4(2) .
C3 C2 C1 118.5(3) .
C3 C2 C7 119.7(3) .
C1 C2 C7 121.7(2) .
O1 C1 C2 122.6(3) .
O1 C1 C6 116.6(2) .
C2 C1 C6 120.7(2) .
C4 C5 C6 121.4(3) .
C5 C6 C1 118.5(3) .
C5 C6 C8 121.5(3) .
C1 C6 C8 120.0(2) .
O2 C22 C23 123.3(3) .
O2 C22 C21 115.5(2) .
C23 C22 C21 121.3(3) .
C26 C21 C22 117.7(3) .
C26 C21 C8 122.3(3) .
C22 C21 C8 119.9(3) .
C6 C8 C21 114.6(2) .
C5 C4 C3 119.3(3) .
C4 C3 C2 121.6(3) .
O2 C9 C10 107.1(2) 2_567
O3 C12 C13 124.7(3) .
O3 C12 C11 114.2(3) .
C13 C12 C11 121.1(3) .
C2 C7 C11 114.7(2) .
C16 C11 C12 117.0(3) .
C16 C11 C7 123.4(3) .
C12 C11 C7 119.6(3) .
C21 C26 C25 121.8(3) .
O3 C10 C9 106.6(2) 2_567
C12 C13 C14 119.6(3) .
C15 C16 C11 122.1(3) .
C14 C15 C16 119.8(3) .
C6G C1G C2G 114.5(4) .
C6G C1G C7G 122.6(4) .
C2G C1G C7G 122.9(4) .
C15 C14 C13 120.4(3) .
C24 C23 C22 119.3(3) .
C1G C6G C5G 121.4(4) .
C24 C25 C26 119.4(3) .
C25 C24 C23 120.5(3) .
C3G C2G C1G 120.6(4) .
C3G C4G C5G 121.9(6) .
C1G C7G C8G 115.2(4) .
C4G C5G C6G 121.5(5) .
C9G C8G N1G 116.9(5) .
C9G C8G C7G 111.1(4) .
N1G C8G C7G 113.4(3) .
C4G C3G C2G 120.1(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C12 1.370(4) .
O3 C10 1.430(3) .
O2 C22 1.373(4) .
O2 C9 1.427(4) .
O1 C1 1.364(3) .
C2 C3 1.390(4) .
C2 C1 1.397(4) .
C2 C7 1.512(4) .
C1 C6 1.407(4) .
C5 C4 1.381(4) .
C5 C6 1.389(4) .
C6 C8 1.507(4) .
C22 C23 1.395(5) .
C22 C21 1.397(4) .
C21 C26 1.382(4) .
C21 C8 1.519(4) .
C4 C3 1.381(4) .
C9 C10 1.499(4) 2_567
C12 C13 1.381(4) .
C12 C11 1.414(4) .
C7 C11 1.512(4) .
N1G C8G 1.480(5) .
C11 C16 1.387(4) .
C26 C25 1.391(5) .
C10 C9 1.499(4) 2_567
C13 C14 1.388(5) .
C16 C15 1.377(5) .
C15 C14 1.371(5) .
C1G C6G 1.372(5) .
C1G C2G 1.475(7) .
C1G C7G 1.479(6) .
C23 C24 1.382(5) .
C6G C5G 1.380(6) .
C25 C24 1.380(6) .
C2G C3G 1.390(7) .
C4G C3G 1.301(7) .
C4G C5G 1.342(7) .
C7G C8G 1.541(6) .
C8G C9G 1.377(7) .
