#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:17:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178464 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/85/4028568.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_4028568
loop_
_publ_author_name
'Monica Cîrcu'
'Albert Soran'
'Niculina Daniela Hădade'
'Monica Rednic'
'Anamaria Terec'
'Ion Grosu'
_publ_section_title
;
 Cryptands with 1,3,5-Tris(1',3'-dioxan-2'-yl)-benzene Units: Synthesis
 and Structural Investigations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8722
_journal_page_last               8729
_journal_paper_doi               10.1021/jo401432y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C36 H48 O9, C H Cl3'
_chemical_formula_sum            'C37 H49 Cl3 O9'
_chemical_formula_weight         744.11
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                   12.5910(7)
_cell_length_b                   12.5910(7)
_cell_length_c                   43.157(5)
_cell_measurement_reflns_used    4056
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      2.66
_cell_volume                     5925.2(8)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            14367
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9202
_exptl_absorpt_correction_T_min  0.8884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             2364
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0871
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0406P)²+24.3483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                1924
_reflns_number_total             2325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401432y_si_002.cif
_cod_data_source_block           122alb
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4028568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.1674(3) 0.2651(3) 0.11624(9) 0.0431(9) Uani 1 1 d .
C2 C 0.2973(4) 0.2790(4) 0.07451(10) 0.0580(11) Uani 1 1 d .
H2A H 0.2506 0.1919 0.0701 0.070 Uiso 1 1 calc R
H2B H 0.3825 0.3074 0.0696 0.070 Uiso 1 1 calc R
C3 C 0.2510(4) 0.3459(4) 0.05396(10) 0.0636(11) Uani 1 1 d .
C4 C 0.1211(4) 0.3044(4) 0.06520(10) 0.0624(11) Uani 1 1 d .
H4A H 0.0889 0.3492 0.0541 0.075 Uiso 1 1 calc R
H4B H 0.0688 0.2178 0.0607 0.075 Uiso 1 1 calc R
C5 C 0.3325(4) 0.4847(4) 0.05775(13) 0.0873(16) Uani 1 1 d .
H5A H 0.4149 0.5088 0.0517 0.131 Uiso 1 1 calc R
H5B H 0.3319 0.5066 0.0790 0.131 Uiso 1 1 calc R
H5C H 0.3020 0.5258 0.0449 0.131 Uiso 1 1 calc R
C6 C 0.2479(5) 0.3079(5) 0.02035(11) 0.0965(17) Uani 1 1 d .
H6A H 0.2192 0.3506 0.0075 0.145 Uiso 1 1 calc R
H6B H 0.1936 0.2212 0.0184 0.145 Uiso 1 1 calc R
H6C H 0.3289 0.3281 0.0140 0.145 Uiso 1 1 calc R
C7 C 0.0811(3) 0.1259(3) 0.11631(8) 0.0386(8) Uani 1 1 d .
C8 C 0.1247(3) 0.0447(3) 0.11657(8) 0.0408(8) Uani 1 1 d .
H8 H 0.2088 0.0748 0.1169 0.049 Uiso 1 1 calc R
C9 C 0.1809(3) 0.3217(3) 0.14791(9) 0.0492(9) Uani 1 1 d .
H9A H 0.2264 0.4104 0.1461 0.059 Uiso 1 1 calc R
H9B H 0.1004 0.2979 0.1562 0.059 Uiso 1 1 calc R
C10 C 0.1918(3) 0.2549(3) 0.19880(9) 0.0530(10) Uani 1 1 d .
H10A H 0.1591 0.3079 0.2041 0.064 Uiso 1 1 calc R
H10B H 0.2558 0.2698 0.2136 0.064 Uiso 1 1 calc R
C11 C 0.0915(3) 0.1232(3) 0.20082(8) 0.0432(8) Uani 1 1 d .
C12 C 0.1215(3) 0.0311(3) 0.20084(8) 0.0446(9) Uani 1 1 d .
H12 H 0.2036 0.0522 0.2009 0.054 Uiso 1 1 calc R
C13 C 0.3333 0.6667 0.94524(19) 0.070(2) Uani 1 3 d S
H13 H 0.3333 0.6667 0.9225 0.084 Uiso 1 3 calc SR
Cl1 Cl 0.35197(17) 0.54566(16) 0.95705(5) 0.1363(8) Uani 1 1 d .
O1 O 0.2872(2) 0.2977(2) 0.10656(6) 0.0475(7) Uani 1 1 d .
O2 O 0.1189(2) 0.3245(2) 0.09774(6) 0.0496(7) Uani 1 1 d .
O3 O 0.2428(2) 0.2836(2) 0.16835(6) 0.0496(7) Uani 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 O2 110.9(3) . .
O1 C1 C9 106.1(3) . .
O2 C1 C9 103.6(3) . .
O1 C1 C7 112.1(3) . .
O2 C1 C7 110.9(3) . .
C9 C1 C7 112.7(3) . .
O1 C2 C3 112.6(3) . .
O1 C2 H2A 109.1 . .
C3 C2 H2A 109.1 . .
O1 C2 H2B 109.1 . .
C3 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
C6 C3 C2 109.7(4) . .
C6 C3 C4 109.9(4) . .
C2 C3 C4 105.4(3) . .
C6 C3 C5 111.0(4) . .
C2 C3 C5 110.2(4) . .
C4 C3 C5 110.5(4) . .
O2 C4 C3 111.4(3) . .
O2 C4 H4A 109.4 . .
C3 C4 H4A 109.4 . .
O2 C4 H4B 109.4 . .
C3 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 C8 118.9(3) . 2
C8 C7 C1 122.0(3) . .
C8 C7 C1 119.1(3) 2 .
C7 C8 C7 121.1(3) . 3
C7 C8 H8 119.5 . .
C7 C8 H8 119.5 3 .
O3 C9 C1 110.9(3) . .
O3 C9 H9A 109.5 . .
C1 C9 H9A 109.5 . .
O3 C9 H9B 109.5 . .
C1 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
O3 C10 C11 110.9(3) . .
O3 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
O3 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C12 C11 C12 118.6(4) 2 .
C12 C11 C10 121.8(3) 2 .
C12 C11 C10 119.5(3) . .
C11 C12 C11 121.4(4) 3 .
C11 C12 H12 119.3 3 .
C11 C12 H12 119.3 . .
Cl1 C13 Cl1 111.7(2) 3_565 2_665
Cl1 C13 Cl1 111.7(2) 3_565 .
Cl1 C13 Cl1 111.7(2) 2_665 .
Cl1 C13 H13 107.1 3_565 .
Cl1 C13 H13 107.1 2_665 .
Cl1 C13 H13 107.1 . .
C1 O1 C2 114.2(3) . .
C1 O2 C4 113.9(3) . .
C9 O3 C10 114.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.414(4) .
C1 O2 1.424(4) .
C1 C9 1.511(5) .
C1 C7 1.532(4) .
C2 O1 1.420(5) .
C2 C3 1.525(6) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C6 1.522(6) .
C3 C4 1.526(6) .
C3 C5 1.530(6) .
C4 O2 1.430(5) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.381(4) .
C7 C8 1.389(4) 2
C8 C7 1.389(4) 3
C8 H8 0.9300 .
C9 O3 1.411(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O3 1.428(4) .
C10 C11 1.503(5) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.383(5) 2
C11 C12 1.388(5) .
C12 C11 1.383(5) 3
C12 H12 0.9300 .
C13 Cl1 1.730(3) 3_565
C13 Cl1 1.730(3) 2_665
C13 Cl1 1.730(3) .
C13 H13 0.9800 .
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 C2 C3 C6 -172.2(4) . .
O1 C2 C3 C4 -53.9(4) . .
O1 C2 C3 C5 65.3(4) . .
C6 C3 C4 O2 172.6(3) . .
C2 C3 C4 O2 54.4(4) . .
C5 C3 C4 O2 -64.7(4) . .
O1 C1 C7 C8 19.0(5) . .
O2 C1 C7 C8 143.7(3) . .
C9 C1 C7 C8 -100.7(4) . .
O1 C1 C7 C8 -161.9(3) . 2
O2 C1 C7 C8 -37.3(4) . 2
C9 C1 C7 C8 78.4(4) . 2
C8 C7 C8 C7 1.6(7) 2 3
C1 C7 C8 C7 -179.3(2) . 3
O1 C1 C9 O3 -55.7(3) . .
O2 C1 C9 O3 -172.6(3) . .
C7 C1 C9 O3 67.4(4) . .
O3 C10 C11 C12 -103.2(4) . 2
O3 C10 C11 C12 72.9(4) . .
C12 C11 C12 C11 0.1(7) 2 3
C10 C11 C12 C11 -176.1(3) . 3
O2 C1 O1 C2 -53.4(4) . .
C9 C1 O1 C2 -165.3(3) . .
C7 C1 O1 C2 71.3(4) . .
C3 C2 O1 C1 55.9(4) . .
O1 C1 O2 C4 54.5(4) . .
C9 C1 O2 C4 168.0(3) . .
C7 C1 O2 C4 -70.9(4) . .
C3 C4 O2 C1 -57.5(4) . .
C1 C9 O3 C10 -138.4(3) . .
C11 C10 O3 C9 87.6(4) . .
