#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:49:28 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178407 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/28/4022856.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_4022856
loop_
_publ_author_name
'Josep Lluís Torres'
'Anna Carreras'
'Aurora Jiménez'
'Enric Brillas'
'Xavier Torrelles'
'Jordi Rius'
'Luis Juliá'
_publ_section_title
;
 Reducing Power of Simple Polyphenols by Electron-Transfer
 Reactions Using a New Stable Radical of the PTM Series,
 Tris(2,3,5,6-tetrachloro-4-nitrophenyl)methyl Radical
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3750
_journal_page_last               3756
_journal_paper_doi               10.1021/jo062665a
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C19 Cl12 N3 O6'
_chemical_formula_weight         791.66
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.87
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.581
_cell_length_b                   20.907
_cell_length_c                   9.078
_cell_measurement_temperature    293(2)
_cell_volume                     3130.5
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_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    0.0214
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4563
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    1.100
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             1548
_refine_diff_density_max         1.214
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.120
_refine_ls_goodness_of_fit_obs   1.228
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_restrained_S_obs      1.228
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_obs          0.0776
_refine_ls_shift/esd_max         0.085
_refine_ls_shift/esd_mean        0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1898P)²+1.1680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2723
_refine_ls_wR_factor_obs         0.2598
_reflns_number_observed          3485
_reflns_number_total             4563
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo062665asi20070315_085423.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1898P)^2^+1.1680P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1898P)^2^+1.1680P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022856
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.28075(10) 0.08208(7) -0.2825(2) 0.0927(5) Uani 1 d .
Cl2 Cl 0.40408(8) 0.16151(6) -0.43815(11) 0.0745(4) Uani 1 d .
Cl3 Cl 0.47218(6) 0.29836(5) 0.06508(10) 0.0590(3) Uani 1 d .
Cl4 Cl 0.33985(8) 0.22315(7) 0.20778(11) 0.0762(4) Uani 1 d .
Cl5 Cl 0.65371(5) 0.32852(5) -0.11635(12) 0.0663(3) Uani 1 d .
Cl6 Cl 0.65232(8) 0.47627(6) -0.1215(2) 0.0870(4) Uani 1 d .
C1 C 0.3214(2) 0.1563(2) -0.0459(4) 0.0514(7) Uani 1 d .
C2 C 0.3349(2) 0.1421(2) -0.1886(4) 0.0547(8) Uani 1 d .
C3 C 0.3919(2) 0.1774(2) -0.2570(3) 0.0484(7) Uani 1 d .
C4 C 0.4364(2) 0.22692(13) -0.1807(3) 0.0408(6) Uani 1 d .
C5 C 0.4190(2) 0.24078(15) -0.0361(3) 0.0432(6) Uani 1 d .
C6 C 0.3610(2) 0.2058(2) 0.0314(4) 0.0474(7) Uani 1 d .
C7 C 0.5000 0.2625(2) -0.2500 0.0605(14) Uani 1 d S
C8 C 0.5000 0.3334(2) -0.2500 0.0392(8) Uani 1 d S
C9 C 0.5687(2) 0.36768(15) -0.1940(3) 0.0444(6) Uani 1 d .
C10 C 0.5690(2) 0.4351(2) -0.1944(4) 0.0525(7) Uani 1 d .
C11 C 0.5000 0.4657(2) -0.2500 0.0545(11) Uani 1 d S
N1 N 0.2629(2) 0.1168(2) 0.0278(4) 0.0632(8) Uani 1 d .
N2 N 0.5000 0.5372(2) -0.2500 0.077(2) Uani 1 d S
O1 O 0.1954(2) 0.1359(2) 0.0281(5) 0.0932(11) Uani 1 d .
O2 O 0.2873(3) 0.0663(2) 0.0778(6) 0.107(2) Uani 1 d .
O3 O 0.4720(4) 0.5627(2) -0.1492(6) 0.120(2) Uani 1 d .
04 O 0.5000 0.1067(3) 0.2500 0.103(2) Uiso 1 d S
O5 O 0.5000 0.0000 0.5000 0.103(2) Uiso 0.256(15) d SP
O6 O 0.4934(11) -0.0219(8) 0.3391(18) 0.103(2) Uiso 0.269(11) d P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
C2 C1 C6 121.9(3) . .
C2 C1 N1 118.9(3) . .
C6 C1 N1 119.2(3) . .
C1 C2 C3 119.3(3) . .
C1 C2 Cl1 120.0(3) . .
C3 C2 Cl1 120.7(3) . .
C2 C3 C4 121.0(3) . .
C2 C3 Cl2 118.4(3) . .
C4 C3 Cl2 120.5(2) . .
C5 C4 C3 117.6(3) . .
C5 C4 C7 121.2(3) . .
C3 C4 C7 121.2(3) . .
C6 C5 C4 121.3(3) . .
C6 C5 Cl3 118.3(2) . .
C4 C5 Cl3 120.3(2) . .
C1 C6 C5 118.9(3) . .
C1 C6 Cl4 120.2(3) . .
C5 C6 Cl4 120.9(3) . .
C4 C7 C4 119.8(4) . 2_654
C4 C7 C8 120.1(2) . .
C4 C7 C8 120.1(2) 2_654 .
C9 C8 C9 118.3(4) . 2_654
C9 C8 C7 120.9(2) . .
C9 C8 C7 120.9(2) 2_654 .
C8 C9 C10 121.0(3) . .
C8 C9 Cl5 120.6(2) . .
C10 C9 Cl5 118.4(3) . .
C11 C10 C9 117.8(3) . .
C11 C10 Cl6 121.7(3) . .
C9 C10 Cl6 120.5(3) . .
C10 C11 C10 124.1(4) 2_654 .
C10 C11 N2 118.0(2) 2_654 .
C10 C11 N2 118.0(2) . .
O1 N1 O2 125.1(4) . .
O1 N1 C1 118.2(4) . .
O2 N1 C1 116.6(4) . .
O3 N2 O3 127.0(5) . 2_654
O3 N2 C11 116.5(3) . .
O3 N2 C11 116.5(3) 2_654 .
O6 O5 O6 180.000(3) . 5_656
O5 O6 O6 158.9(12) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.717(3) .
Cl2 C3 1.710(3) .
Cl3 C5 1.705(3) .
Cl4 C6 1.713(3) .
Cl5 C9 1.717(3) .
Cl6 C10 1.703(4) .
C1 C2 1.370(5) .
C1 C6 1.378(5) .
C1 N1 1.484(4) .
C2 C3 1.395(4) .
C3 C4 1.411(4) .
C4 C5 1.402(4) .
C4 C7 1.481(3) .
C5 C6 1.399(4) .
C7 C4 1.481(3) 2_654
C7 C8 1.483(6) .
C8 C9 1.397(4) .
C8 C9 1.397(4) 2_654
C9 C10 1.410(5) .
C10 C11 1.361(5) .
C11 C10 1.361(5) 2_654
C11 N2 1.495(6) .
N1 O1 1.189(5) .
N1 O2 1.203(6) .
N2 O3 1.194(4) .
N2 O3 1.194(4) 2_654
O5 O6 1.52(2) .
O5 O6 1.52(2) 5_656
O6 O6 1.65(3) 2_655
