#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:16:28 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178892 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/21/4112147.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_4112147
loop_
_publ_author_name
'Daniel Maspoch'
'Neus Domingo'
'Daniel Ruiz-Molina'
'Klaus Wurst'
'Javier Tejada'
'Concepció Rovira'
'Jaume Veciana'
_publ_section_title
;
 A Robust Nanocontainer Based on a Pure Organic Free Radical
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              730
_journal_page_last               731
_journal_paper_doi               10.1021/ja038988v
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C27 H16 Cl13 O4'
_chemical_formula_weight         865.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_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            18
_cell_length_a                   31.4651(6)
_cell_length_b                   31.4651(7)
_cell_length_c                   18.8447(7)
_cell_measurement_reflns_used    22698
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      1.0
_cell_volume                     16157.6(8)
_computing_data_collection       'Kappa CCD'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '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  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19275
_diffrn_reflns_theta_full        19.99
_diffrn_reflns_theta_max         19.99
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.032
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       prism
_exptl_crystal_F_000             7758
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    'refined with bond restraints at O2 and O4'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0696P)²+63.9858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                2592
_reflns_number_total             3346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038988vsi20031010_120803.cif
_cod_data_source_block           ff
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4112147
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65424(15) 0.22329(15) 0.8477(3) 0.0706(12) Uani 1 1 d . . .
O2 O 0.71354(18) 0.22570(18) 0.7813(3) 0.0722(13) Uani 1 1 d D . .
H2 H 0.730(4) 0.255(2) 0.799(6) 0.22(6) Uiso 1 1 d D . .
O3 O 0.67216(17) -0.11238(15) 0.8526(3) 0.0763(14) Uani 1 1 d . . .
O4 O 0.6195(2) -0.1674(2) 0.7805(3) 0.0969(18) Uani 1 1 d D . .
H4 H 0.636(4) -0.180(4) 0.797(6) 0.20(6) Uiso 1 1 d D . .
C1 C 0.6713(3) 0.2036(2) 0.8109(4) 0.0555(16) Uani 1 1 d . . .
C2 C 0.6376(2) -0.1291(2) 0.8112(4) 0.0499(16) Uani 1 1 d . . .
C3 C 0.6429(2) 0.1484(2) 0.8001(3) 0.0456(15) Uani 1 1 d . . .
C4 C 0.6040(2) 0.1286(2) 0.7516(3) 0.0434(14) Uani 1 1 d . . .
C5 C 0.57435(18) 0.0778(2) 0.7467(3) 0.0392(14) Uani 1 1 d . . .
C6 C 0.58154(19) 0.04615(19) 0.7914(3) 0.0385(14) Uani 1 1 d . . .
C7 C 0.6213(2) 0.0677(2) 0.8380(3) 0.0474(15) Uani 1 1 d . . .
C8 C 0.6517(2) 0.1177(2) 0.8412(3) 0.0482(15) Uani 1 1 d . . .
C9 C 0.5479(2) -0.0070(2) 0.7901(3) 0.0452(15) Uani 1 1 d . . .
C10 C 0.56805(19) -0.04034(19) 0.7914(3) 0.0395(14) Uani 1 1 d . . .
C11 C 0.60524(19) -0.03482(18) 0.7438(3) 0.0385(13) Uani 1 1 d . . .
C12 C 0.62688(19) -0.0637(2) 0.7495(3) 0.0419(14) Uani 1 1 d . . .
C13 C 0.6114(2) -0.09952(19) 0.8014(3) 0.0459(15) Uani 1 1 d . . .
C14 C 0.5736(2) -0.1070(2) 0.8465(3) 0.0502(15) Uani 1 1 d . . .
C15 C 0.5527(2) -0.0775(2) 0.8423(3) 0.0499(15) Uani 1 1 d . . .
C16 C 0.4949(2) -0.0267(2) 0.7932(3) 0.0434(14) Uani 1 1 d . . .
C17 C 0.4625(2) -0.0649(2) 0.7484(3) 0.0520(16) Uani 1 1 d . . .
C18 C 0.4123(2) -0.0826(2) 0.7506(4) 0.0654(18) Uani 1 1 d . . .
C19 C 0.3933(2) -0.0624(3) 0.7979(4) 0.072(2) Uani 1 1 d . . .
C20 C 0.4243(3) -0.0254(3) 0.8426(4) 0.0694(19) Uani 1 1 d . . .
C21 C 0.4742(2) -0.0072(2) 0.8415(3) 0.0556(16) Uani 1 1 d . . .
Cl1 Cl 0.59515(6) 0.16745(5) 0.69792(8) 0.0556(5) Uani 1 1 d . . .
Cl2 Cl 0.52843(5) 0.05396(5) 0.68371(7) 0.0465(4) Uani 1 1 d . . .
Cl3 Cl 0.63114(6) 0.03254(6) 0.89905(9) 0.0706(5) Uani 1 1 d . . .
Cl4 Cl 0.70076(6) 0.14347(6) 0.89914(10) 0.0785(6) Uani 1 1 d . . .
Cl5 Cl 0.62325(5) 0.00796(5) 0.67692(7) 0.0531(4) Uani 1 1 d . . .
Cl6 Cl 0.67257(6) -0.05635(6) 0.69191(8) 0.0603(5) Uani 1 1 d . . .
Cl7 Cl 0.55369(7) -0.15285(6) 0.90846(10) 0.0807(6) Uani 1 1 d . . .
Cl8 Cl 0.51057(7) -0.08474(7) 0.90621(9) 0.0815(6) Uani 1 1 d . . .
Cl9 Cl 0.48535(6) -0.08890(6) 0.68707(9) 0.0693(5) Uani 1 1 d . . .
Cl10 Cl 0.37404(7) -0.12818(8) 0.69337(12) 0.1027(7) Uani 1 1 d . . .
Cl11 Cl 0.33148(7) -0.08285(10) 0.79846(15) 0.1266(9) Uani 1 1 d . . .
Cl12 Cl 0.40057(8) -0.00092(9) 0.90310(12) 0.1035(7) Uani 1 1 d . . .
Cl13 Cl 0.51037(6) 0.03517(7) 0.90398(9) 0.0760(5) Uani 1 1 d . . .
C22 C 0.3333 -0.3333 1.047(2) 0.320(19) Uiso 1 3 d SD . 1
C23 C 0.360(2) -0.2948(16) 0.990(2) 0.29(3) Uiso 0.33 1 d PD . 1
C25 C 0.379(2) -0.2134(16) 0.936(3) 0.28(3) Uiso 0.33 1 d PD A 1
C24 C 0.343(2) -0.258(2) 0.979(4) 0.34(4) Uiso 0.33 1 d PD A 1
C26 C 0.361(2) -0.1766(16) 0.927(4) 0.24(3) Uiso 0.33 1 d PD A 1
C27 C 0.3914(14) -0.1297(14) 0.9690(19) 0.152(13) Uiso 0.33 1 d PD A 1
C22A C 0.261(3) -0.318(3) 0.745(4) 0.33(4) Uiso 0.33 1 d PD B 2
C23A C 0.260(3) -0.274(3) 0.778(4) 0.30(5) Uiso 0.33 1 d PD B 2
C24A C 0.300(3) -0.253(5) 0.835(5) 0.52(9) Uiso 0.33 1 d PD B 2
C25A C 0.344(3) -0.257(4) 0.811(6) 0.60(9) Uiso 0.33 1 d PD B 2
C26A C 0.390(2) -0.219(3) 0.854(4) 0.34(4) Uiso 0.33 1 d PD B 2
C27A C 0.372(3) -0.188(3) 0.893(4) 0.30(4) Uiso 0.33 1 d PD B 2
C22B C 0.228(2) -0.329(2) 0.790(3) 0.25(2) Uiso 0.33 1 d PD C 3
C23B C 0.272(4) -0.278(3) 0.777(4) 0.54(12) Uiso 0.33 1 d PD C 3
C24B C 0.277(2) -0.245(3) 0.840(7) 0.50(8) Uiso 0.33 1 d PD C 3
C25B C 0.3297(18) -0.2186(19) 0.868(2) 0.201(17) Uiso 0.33 1 d PD C 3
C26B C 0.343(3) -0.171(2) 0.906(4) 0.32(4) Uiso 0.33 1 d PD C 3
C27B C 0.3775(18) -0.1658(18) 0.967(2) 0.182(16) Uiso 0.33 1 d PD C 3
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
H2 O2 C1 109(8) . .
H4 O4 C2 101(8) . .
O1 C1 O2 124.9(6) . .
O1 C1 C3 120.0(6) . .
O2 C1 C3 115.0(6) . .
O4 C2 O3 127.8(6) . .
O4 C2 C13 115.3(6) . .
O3 C2 C13 116.7(5) . .
C8 C3 C4 119.6(5) . .
C8 C3 C1 121.3(5) . .
C4 C3 C1 118.9(5) . .
C5 C4 C3 119.4(5) . .
C5 C4 Cl1 121.7(4) . .
C3 C4 Cl1 118.9(4) . .
C4 C5 C6 121.3(5) . .
C4 C5 Cl2 118.6(4) . .
C6 C5 Cl2 120.1(4) . .
C7 C6 C5 117.1(5) . .
C7 C6 C9 121.7(5) . .
C5 C6 C9 121.2(5) . .
C8 C7 C6 121.7(5) . .
C8 C7 Cl3 117.3(4) . .
C6 C7 Cl3 120.8(4) . .
C3 C8 C7 120.8(5) . .
C3 C8 Cl4 118.4(4) . .
C7 C8 Cl4 120.8(5) . .
C16 C9 C6 120.1(5) . .
C16 C9 C10 120.3(5) . .
C6 C9 C10 119.4(5) . .
C15 C10 C11 117.1(5) . .
C15 C10 C9 121.1(5) . .
C11 C10 C9 121.7(5) . .
C12 C11 C10 121.3(5) . .
C12 C11 Cl5 119.4(4) . .
C10 C11 Cl5 119.3(4) . .
C11 C12 C13 120.0(5) . .
C11 C12 Cl6 121.0(4) . .
C13 C12 Cl6 118.9(4) . .
C14 C13 C12 119.6(5) . .
C14 C13 C2 120.1(5) . .
C12 C13 C2 120.2(5) . .
C15 C14 C13 120.6(5) . .
C15 C14 Cl7 120.5(5) . .
C13 C14 Cl7 119.0(4) . .
C14 C15 C10 121.2(5) . .
C14 C15 Cl8 117.8(5) . .
C10 C15 Cl8 120.8(4) . .
C17 C16 C21 117.5(5) . .
C17 C16 C9 121.6(5) . .
C21 C16 C9 121.0(5) . .
C18 C17 C16 121.2(6) . .
C18 C17 Cl9 119.0(5) . .
C16 C17 Cl9 119.7(4) . .
C17 C18 C19 119.9(6) . .
C17 C18 Cl10 119.9(6) . .
C19 C18 Cl10 120.2(6) . .
C20 C19 C18 119.7(6) . .
C20 C19 Cl11 120.4(6) . .
C18 C19 Cl11 119.9(6) . .
C19 C20 C21 121.5(6) . .
C19 C20 Cl12 119.9(5) . .
C21 C20 Cl12 118.6(6) . .
C20 C21 C16 120.2(6) . .
C20 C21 Cl13 119.2(5) . .
C16 C21 Cl13 120.4(4) . .
C23 C22 C23 76(4) 2_545 .
C23 C22 C23 76(4) 2_545 3_655
C23 C22 C23 76(4) . 3_655
C22 C23 C24 117(3) . .
C22 C23 C23 52.0(19) . 3_655
C24 C23 C23 149(5) . 3_655
C22 C23 C23 52.0(19) . 2_545
C24 C23 C23 90(5) . 2_545
C23 C23 C23 60.000(4) 3_655 2_545
C24 C25 C26 111(3) . .
C23 C24 C25 113(3) . .
C27 C26 C25 113(3) . .
C22A C23A C24A 106(3) . .
C25A C24A C23A 111(3) . .
C24A C25A C26A 108(3) . .
C27A C26A C25A 105(3) . .
C22B C23B C24B 109(3) . .
C25B C24B C23B 111(4) . .
C24B C25B C26B 113(3) . .
C25B C26B C27B 106(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.220(7) .
O2 H2 0.87(3) .
O2 C1 1.279(7) .
O3 C2 1.225(7) .
O4 H4 0.84(3) .
O4 C2 1.195(7) .
C1 C3 1.515(8) .
C2 C13 1.529(8) .
C3 C8 1.371(8) .
C3 C4 1.399(7) .
C4 C5 1.393(7) .
C4 Cl1 1.714(6) .
C5 C6 1.406(7) .
C5 Cl2 1.725(5) .
C6 C7 1.395(7) .
C6 C9 1.465(7) .
C7 C8 1.376(8) .
C7 Cl3 1.728(6) .
C8 Cl4 1.726(6) .
C9 C16 1.463(7) .
C9 C10 1.471(7) .
C10 C15 1.399(7) .
C10 C11 1.414(7) .
C11 C12 1.384(7) .
C11 Cl5 1.721(5) .
C12 C13 1.385(7) .
C12 Cl6 1.722(5) .
C13 C14 1.383(8) .
C14 C15 1.383(8) .
C14 Cl7 1.712(6) .
C15 Cl8 1.719(6) .
C16 C17 1.406(8) .
C16 C21 1.421(8) .
C17 C18 1.388(8) .
C17 Cl9 1.722(6) .
C18 C19 1.391(9) .
C18 Cl10 1.714(7) .
C19 C20 1.371(10) .
C19 Cl11 1.716(7) .
C20 C21 1.378(9) .
C20 Cl12 1.740(7) .
C21 Cl13 1.716(6) .
C22 C23 1.51(2) 2_545
C22 C23 1.51(2) .
C22 C23 1.51(2) 3_655
C23 C24 1.52(2) .
C23 C23 1.86(8) 3_655
C23 C23 1.86(8) 2_545
C25 C24 1.52(2) .
C25 C26 1.53(2) .
C26 C27 1.52(2) .
C22A C23A 1.53(2) .
C23A C24A 1.54(2) .
C24A C25A 1.53(2) .
C25A C26A 1.54(2) .
C26A C27A 1.53(2) .
C22B C23B 1.53(2) .
C23B C24B 1.53(2) .
C24B C25B 1.52(2) .
C25B C26B 1.53(2) .
C26B C27B 1.53(2) .
