#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023275.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_4023275
loop_
_publ_author_name
'Yangping Liu'
'Frederick A. Villamena'
'Jian Sun'
'Yingkai Xu'
'Ilirian Dhimitruka'
'Jay L. Zweier'
_publ_section_title
;
 Synthesis and Characterization of Ester-Derivatized
 Tetrathiatriarylmethyl Radicals as Intracellular Oxygen Probes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1490
_journal_page_last               1497
_journal_paper_doi               10.1021/jo7022747
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C43 H45 O6 S12, 3(C H2 Cl2)'
_chemical_formula_sum            'C46 H51 Cl6 O6 S12'
_chemical_formula_weight         1297.29
_chemical_name_common            'Zweier 1546'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      146
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-04-19T11:24:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   21.2273(3)
_cell_length_b                   21.2273(3)
_cell_length_c                   11.3541(2)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     4430.70(12)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.258598E-1
_diffrn_orient_matrix_UB_12      -0.413695E-1
_diffrn_orient_matrix_UB_13      -0.240596E-1
_diffrn_orient_matrix_UB_21      0.245763E-1
_diffrn_orient_matrix_UB_22      -0.37974E-1
_diffrn_orient_matrix_UB_23      0.302161E-1
_diffrn_orient_matrix_UB_31      -0.74363E-1
_diffrn_orient_matrix_UB_32      -0.471776E-1
_diffrn_orient_matrix_UB_33      0.11928E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30981
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark purple-brown'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             2007
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0735P)²+9.1446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                4077
_reflns_number_total             4526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7022747-File001.cif
_cod_data_source_block           Zweier1546
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4023275
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'
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 0.6667 0.3333 0.6283(5) 0.0166(10) Uani 1 3 d S . .
C2 C 0.74275(16) 0.35357(17) 0.6273(3) 0.0169(6) Uani 1 1 d . . .
C3 C 0.76888(16) 0.31839(16) 0.7024(3) 0.0167(6) Uani 1 1 d . . .
C4 C 0.84268(17) 0.33931(17) 0.7046(3) 0.0190(6) Uani 1 1 d . . .
C5 C 0.89200(17) 0.39281(17) 0.6275(3) 0.0181(6) Uani 1 1 d . . .
C6 C 0.86637(17) 0.42770(17) 0.5513(3) 0.0186(6) Uani 1 1 d . . .
C7 C 0.79379(16) 0.40989(16) 0.5537(3) 0.0162(6) Uani 1 1 d . . .
C8 C 0.78478(19) 0.26508(19) 0.9024(3) 0.0243(7) Uani 1 1 d . . .
C9 C 0.7982(2) 0.3253(2) 0.9890(4) 0.0379(9) Uani 1 1 d . . .
H9A H 0.7535 0.3115 1.0334 0.057 Uiso 1 1 calc R . .
H9B H 0.8126 0.3705 0.9458 0.057 Uiso 1 1 calc R . .
H9C H 0.8371 0.3328 1.0437 0.057 Uiso 1 1 calc R . .
C10 C 0.7653(2) 0.1943(2) 0.9661(4) 0.0356(9) Uani 1 1 d . . .
H10A H 0.8034 0.2032 1.0235 0.053 Uiso 1 1 calc R . .
H10B H 0.7613 0.158 0.9087 0.053 Uiso 1 1 calc R . .
H10C H 0.7188 0.1762 1.007 0.053 Uiso 1 1 calc R . .
C11 C 0.84434(18) 0.48177(19) 0.3549(3) 0.0247(7) Uani 1 1 d . . .
C12 C 0.8635(2) 0.5529(2) 0.2927(3) 0.0347(9) Uani 1 1 d . . .
H12A H 0.9082 0.5695 0.2468 0.052 Uiso 1 1 calc R . .
H12B H 0.871 0.5898 0.3514 0.052 Uiso 1 1 calc R . .
H12C H 0.8237 0.545 0.2399 0.052 Uiso 1 1 calc R . .
C13 C 0.8244(2) 0.4205(2) 0.2675(4) 0.0363(9) Uani 1 1 d . . .
H13A H 0.7828 0.4135 0.2201 0.054 Uiso 1 1 calc R . .
H13B H 0.8115 0.3755 0.3103 0.054 Uiso 1 1 calc R . .
H13C H 0.8659 0.4329 0.2158 0.054 Uiso 1 1 calc R . .
C14 C 0.97024(17) 0.41579(18) 0.6220(3) 0.0229(7) Uani 1 1 d . . .
C15 C 1.0601(2) 0.3870(3) 0.6751(4) 0.0374(9) Uani 1 1 d . . .
H15A H 1.0793 0.3924 0.5949 0.056 Uiso 1 1 calc R . .
H15B H 1.0649 0.3489 0.7162 0.056 Uiso 1 1 calc R . .
H15C H 1.0877 0.4331 0.7175 0.056 Uiso 1 1 calc R . .
O1 O 1.01593(13) 0.47136(14) 0.5763(3) 0.0336(6) Uani 1 1 d . . .
O2 O 0.98458(13) 0.36695(14) 0.6701(2) 0.0286(5) Uani 1 1 d . . .
S1 S 0.71201(4) 0.24866(4) 0.79998(7) 0.02267(18) Uani 1 1 d . . .
S2 S 0.86581(4) 0.29298(5) 0.81055(7) 0.02478(19) Uani 1 1 d . . .
S3 S 0.76877(4) 0.45786(4) 0.45598(7) 0.02196(18) Uani 1 1 d . . .
S4 S 0.92073(5) 0.49472(4) 0.44752(7) 0.02527(19) Uani 1 1 d . . .
Cl1 Cl 0.71213(12) 0.04490(10) 0.70784(16) 0.0898(5) Uani 1 1 d . . .
Cl2 Cl 0.83223(16) 0.1338(2) 0.5529(3) 0.1728(17) Uani 1 1 d . . .
C1A C 0.7553(4) 0.1214(4) 0.6161(6) 0.0714(16) Uani 1 1 d . . .
H1A1 H 0.7209 0.1168 0.5532 0.086 Uiso 1 1 calc R . .
H1A2 H 0.7668 0.1652 0.6629 0.086 Uiso 1 1 calc R . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C2 C1 C2 119.994(8) . 3_665 ?
C2 C1 C2 119.994(9) . 2_655 ?
C2 C1 C2 119.994(8) 3_665 2_655 ?
C7 C2 C3 117.7(3) . . ?
C7 C2 C1 121.6(3) . . ?
C3 C2 C1 120.7(3) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 S1 116.4(2) . . ?
C2 C3 S1 122.6(2) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 S2 114.4(2) . . ?
C5 C4 S2 124.9(2) . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 C14 123.6(3) . . ?
C6 C5 C14 117.7(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 S4 115.0(2) . . ?
C5 C6 S4 124.4(2) . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 S3 116.4(2) . . ?
C2 C7 S3 122.4(2) . . ?
C9 C8 C10 111.4(3) . . ?
C9 C8 S1 110.9(3) . . ?
C10 C8 S1 109.1(3) . . ?
C9 C8 S2 110.1(3) . . ?
C10 C8 S2 109.6(2) . . ?
S1 C8 S2 105.49(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C12 111.6(3) . . ?
C13 C11 S3 110.0(3) . . ?
C12 C11 S3 109.2(2) . . ?
C13 C11 S4 110.5(3) . . ?
C12 C11 S4 109.8(3) . . ?
S3 C11 S4 105.61(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 O2 123.4(3) . . ?
O1 C14 C5 124.1(3) . . ?
O2 C14 C5 112.4(3) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 O2 C15 116.1(3) . . ?
C3 S1 C8 94.67(15) . . ?
C4 S2 C8 95.15(14) . . ?
C7 S3 C11 94.58(15) . . ?
C6 S4 C11 95.13(15) . . ?
Cl2 C1A Cl1 114.6(4) . . ?
Cl2 C1A H1A1 108.6 . . ?
Cl1 C1A H1A1 108.6 . . ?
Cl2 C1A H1A2 108.6 . . ?
Cl1 C1A H1A2 108.6 . . ?
H1A1 C1A H1A2 107.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.449(3) . ?
C1 C2 1.449(3) 3_665 ?
C1 C2 1.449(3) 2_655 ?
C2 C7 1.416(5) . ?
C2 C3 1.416(4) . ?
C3 C4 1.399(4) . ?
C3 S1 1.757(3) . ?
C4 C5 1.401(5) . ?
C4 S2 1.772(3) . ?
C5 C6 1.413(5) . ?
C5 C14 1.480(4) . ?
C6 C7 1.391(4) . ?
C6 S4 1.761(3) . ?
C7 S3 1.758(3) . ?
C8 C9 1.523(5) . ?
C8 C10 1.527(5) . ?
C8 S1 1.822(3) . ?
C8 S2 1.838(4) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C13 1.519(5) . ?
C11 C12 1.526(5) . ?
C11 S3 1.826(3) . ?
C11 S4 1.835(4) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 O1 1.207(4) . ?
C14 O2 1.334(4) . ?
C15 O2 1.440(4) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
Cl1 C1A 1.753(7) . ?
Cl2 C1A 1.679(7) . ?
C1A H1A1 0.99 . ?
C1A H1A2 0.99 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C7 135.8(3) 3_665 . . . ?
C2 C1 C2 C7 -42.7(6) 2_655 . . . ?
C2 C1 C2 C3 -45.6(6) 3_665 . . . ?
C2 C1 C2 C3 135.9(3) 2_655 . . . ?
C7 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C4 -177.9(3) . . . . ?
C7 C2 C3 S1 179.0(2) . . . . ?
C1 C2 C3 S1 0.3(4) . . . . ?
C2 C3 C4 C5 -3.7(4) . . . . ?
S1 C3 C4 C5 178.0(2) . . . . ?
C2 C3 C4 S2 176.2(2) . . . . ?
S1 C3 C4 S2 -2.1(3) . . . . ?
C3 C4 C5 C6 3.0(4) . . . . ?
S2 C4 C5 C6 -177.0(2) . . . . ?
C3 C4 C5 C14 -177.8(3) . . . . ?
S2 C4 C5 C14 2.3(5) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C14 C5 C6 C7 -178.6(3) . . . . ?
C4 C5 C6 S4 -178.8(2) . . . . ?
C14 C5 C6 S4 1.9(4) . . . . ?
C5 C6 C7 C2 -3.7(5) . . . . ?
S4 C6 C7 C2 175.9(2) . . . . ?
C5 C6 C7 S3 179.2(2) . . . . ?
S4 C6 C7 S3 -1.2(3) . . . . ?
C3 C2 C7 C6 2.9(5) . . . . ?
C1 C2 C7 C6 -178.4(3) . . . . ?
C3 C2 C7 S3 179.8(2) . . . . ?
C1 C2 C7 S3 -1.5(5) . . . . ?
C4 C5 C14 O1 -163.1(3) . . . . ?
C6 C5 C14 O1 16.2(5) . . . . ?
C4 C5 C14 O2 18.9(4) . . . . ?
C6 C5 C14 O2 -161.8(3) . . . . ?
O1 C14 O2 C15 5.7(5) . . . . ?
C5 C14 O2 C15 -176.3(3) . . . . ?
C4 C3 S1 C8 23.9(3) . . . . ?
C2 C3 S1 C8 -154.4(3) . . . . ?
C9 C8 S1 C3 84.4(3) . . . . ?
C10 C8 S1 C3 -152.5(3) . . . . ?
S2 C8 S1 C3 -34.78(18) . . . . ?
C3 C4 S2 C8 -20.7(3) . . . . ?
C5 C4 S2 C8 159.3(3) . . . . ?
C9 C8 S2 C4 -85.7(3) . . . . ?
C10 C8 S2 C4 151.5(3) . . . . ?
S1 C8 S2 C4 34.10(19) . . . . ?
C6 C7 S3 C11 22.8(3) . . . . ?
C2 C7 S3 C11 -154.2(3) . . . . ?
C13 C11 S3 C7 85.4(3) . . . . ?
C12 C11 S3 C7 -151.9(3) . . . . ?
S4 C11 S3 C7 -33.90(18) . . . . ?
C7 C6 S4 C11 -21.0(3) . . . . ?
C5 C6 S4 C11 158.6(3) . . . . ?
C13 C11 S4 C6 -85.3(3) . . . . ?
C12 C11 S4 C6 151.2(3) . . . . ?
S3 C11 S4 C6 33.62(19) . . . . ?
