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#$Date: 2016-03-23 15:45:59 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179346 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/43/4324360.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_4324360
loop_
_publ_author_name
'David Schweinfurth'
'Hari Sankar Das'
'Fritz Weisser'
'Denis Bubrin'
'Biprajit Sarkar'
_publ_section_title
;
 One-Pot Synthesis of Symmetric and Asymmetric p-Quinone Ligands and
 Unprecedented Substituent Induced Reactivity in Their Dinuclear Ruthenium
 Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1150
_journal_page_last               1159
_journal_paper_doi               10.1021/ic101972u
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C20 H12 F6 N2 O2'
_chemical_formula_sum            'C20 H12 F6 N2 O2'
_chemical_formula_weight         426.32
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.961(2)
_cell_length_b                   11.829(2)
_cell_length_c                   15.068(3)
_cell_measurement_reflns_used    2235
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      0.41
_cell_volume                     1772.8(6)
_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_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'four-circle, ccd detector'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4072
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Scalepack (W. Minor & Z. Otwinowski)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.308
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0424
_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)+(0.0557P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1673
_reflns_number_total             2165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101972u_si_004.cif
_cod_data_source_block           bs09
_cod_original_cell_volume        1772.9(6)
_cod_database_code               4324360
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O O 0.39779(10) 0.46930(10) -0.16624(7) 0.0201(3) Uani 1 1 d .
N N 0.33903(12) 0.49366(12) 0.14280(8) 0.0170(3) Uani 1 1 d .
H0A H 0.3783 0.5112 0.1931 0.020 Uiso 1 1 calc R
F1 F 0.03390(10) 0.74196(9) 0.14524(8) 0.0366(3) Uani 1 1 d .
C1 C 0.44074(14) 0.48132(13) -0.08823(10) 0.0145(3) Uani 1 1 d .
F2 F 0.20826(11) 0.70345(9) 0.07348(7) 0.0297(3) Uani 1 1 d .
C2 C 0.35933(14) 0.47346(13) -0.01414(10) 0.0158(3) Uani 1 1 d .
H2A H 0.2690 0.4546 -0.0233 0.019 Uiso 1 1 calc R
F3 F 0.21964(10) 0.69874(9) 0.21574(7) 0.0308(3) Uani 1 1 d .
C3 C 0.41080(14) 0.49299(13) 0.07036(10) 0.0140(3) Uani 1 1 d .
C11 C 0.19896(14) 0.46614(13) 0.13929(10) 0.0143(3) Uani 1 1 d .
C12 C 0.10072(14) 0.55094(13) 0.14094(9) 0.0134(3) Uani 1 1 d .
C13 C -0.03459(14) 0.52123(13) 0.13932(10) 0.0151(3) Uani 1 1 d .
H13A H -0.0999 0.5773 0.1412 0.018 Uiso 1 1 calc R
C14 C -0.07243(15) 0.40901(14) 0.13487(11) 0.0192(3) Uani 1 1 d .
H14A H -0.1630 0.3896 0.1341 0.023 Uiso 1 1 calc R
C15 C 0.02455(16) 0.32531(14) 0.13162(12) 0.0225(4) Uani 1 1 d .
H15A H -0.0012 0.2498 0.1280 0.027 Uiso 1 1 calc R
C16 C 0.15990(16) 0.35361(13) 0.13369(11) 0.0200(3) Uani 1 1 d .
H16A H 0.2245 0.2971 0.1313 0.024 Uiso 1 1 calc R
C17 C 0.14015(15) 0.67285(13) 0.14372(10) 0.0190(3) 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'
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'
F F 0.0171 0.0103 '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
C3 N C11 122.14(13) .
C3 N H0A 118.9 .
C11 N H0A 118.9 .
O C1 C2 123.88(13) .
O C1 C3 118.33(13) 5_665
C2 C1 C3 117.79(12) 5_665
C3 C2 C1 121.40(13) .
C3 C2 H2A 119.3 .
C1 C2 H2A 119.3 .
N C3 C2 124.87(13) .
N C3 C1 114.36(12) 5_665
C2 C3 C1 120.76(13) 5_665
C16 C11 C12 119.57(13) .
C16 C11 N 119.33(13) .
C12 C11 N 121.10(14) .
C13 C12 C11 119.67(13) .
C13 C12 C17 119.80(13) .
C11 C12 C17 120.53(13) .
C14 C13 C12 120.35(14) .
C14 C13 H13A 119.8 .
C12 C13 H13A 119.8 .
C13 C14 C15 119.97(14) .
C13 C14 H14A 120.0 .
C15 C14 H14A 120.0 .
C14 C15 C16 120.33(15) .
C14 C15 H15A 119.8 .
C16 C15 H15A 119.8 .
C15 C16 C11 120.09(14) .
C15 C16 H16A 120.0 .
C11 C16 H16A 120.0 .
F1 C17 F2 106.48(13) .
F1 C17 F3 106.20(13) .
F2 C17 F3 105.99(12) .
F1 C17 C12 112.52(12) .
F2 C17 C12 112.50(13) .
F3 C17 C12 112.64(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O C1 1.2372(18) .
N C3 1.3367(19) .
N C11 1.4308(18) .
N H0A 0.8600 .
F1 C17 1.3384(19) .
C1 C2 1.418(2) .
C1 C3 1.519(2) 5_665
F2 C17 1.3375(19) .
C2 C3 1.366(2) .
C2 H2A 0.9300 .
F3 C17 1.3437(18) .
C3 C1 1.519(2) 5_665
C11 C16 1.388(2) .
C11 C12 1.402(2) .
C12 C13 1.392(2) .
C12 C17 1.495(2) .
C13 C14 1.381(2) .
C13 H13A 0.9300 .
C14 C15 1.386(2) .
C14 H14A 0.9300 .
C15 C16 1.388(2) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
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
O C1 C2 C3 -176.73(15) . .
C3 C1 C2 C3 2.7(2) 5_665 .
C11 N C3 C2 4.1(2) . .
C11 N C3 C1 -177.04(14) . 5_665
C1 C2 C3 N 175.92(15) . .
C1 C2 C3 C1 -2.8(3) . 5_665
C3 N C11 C16 77.9(2) . .
C3 N C11 C12 -101.81(18) . .
C16 C11 C12 C13 1.7(2) . .
N C11 C12 C13 -178.65(13) . .
C16 C11 C12 C17 -177.84(14) . .
N C11 C12 C17 1.8(2) . .
C11 C12 C13 C14 -0.9(2) . .
C17 C12 C13 C14 178.64(14) . .
C12 C13 C14 C15 -0.3(2) . .
C13 C14 C15 C16 0.6(2) . .
C14 C15 C16 C11 0.2(3) . .
C12 C11 C16 C15 -1.3(2) . .
N C11 C16 C15 179.00(14) . .
C13 C12 C17 F1 0.6(2) . .
C11 C12 C17 F1 -179.84(13) . .
C13 C12 C17 F2 -119.63(15) . .
C11 C12 C17 F2 59.90(18) . .
C13 C12 C17 F3 120.64(15) . .
C11 C12 C17 F3 -59.83(19) . .
