#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:04:00 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178883 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/12/4111292.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_4111292
loop_
_publ_author_name
'Jian-Ming Lü'
'Sergiy V. Rosokha'
'Ivan S. Neretin'
'Jay K. Kochi'
_publ_section_title
;
 Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis)
 Characteristics and Electron-Transfer Reactivities of Their Reduced Anion
 Radicals as Separated vs Contact Ion Pairs
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16708
_journal_page_last               16719
_journal_paper_doi               10.1021/ja066471o
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C16 H36 N, 1.5(C8 Cl2 N2 O2)'
_chemical_formula_sum            'C28 H36 Cl3 N4 O3'
_chemical_formula_weight         582.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.21(3)
_cell_angle_beta                 97.26(4)
_cell_angle_gamma                108.24(5)
_cell_formula_units_Z            2
_cell_length_a                   9.672(13)
_cell_length_b                   12.917(16)
_cell_length_c                   13.233(16)
_cell_measurement_reflns_used    1118
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.76
_cell_measurement_theta_min      2.27
_cell_volume                     1509(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT & SADABS (Bruker, 2003)'
_computing_molecular_graphics    'XP (Bruker, 1999)'
_computing_publication_material  'SHELXL, XCIF (Bruker, 1999)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_method       'omega-scan, full sphere'
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.2280
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13133
_diffrn_reflns_theta_full        30.44
_diffrn_reflns_theta_max         30.44
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             614
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         8478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.814
_refine_ls_R_factor_all          0.2125
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1811
_reflns_number_gt                2476
_reflns_number_total             8478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja066471osi20061006_023416.cif
_cod_data_source_block           ros62
_cod_database_code               4111292
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.78613(12) 0.33946(10) 0.12760(10) 0.0607(4) Uani 1 1 d . . .
Cl2 Cl 0.50152(14) 0.14807(12) -0.02267(10) 0.0727(4) Uani 1 1 d . . .
C1 C 0.5348(4) 0.2626(3) 0.4419(4) 0.0418(11) Uani 1 1 d . . .
C2 C 0.5296(4) 0.2355(3) 0.3300(3) 0.0354(10) Uani 1 1 d . . .
C3 C 0.6549(4) 0.2949(3) 0.2908(4) 0.0384(11) Uani 1 1 d . . .
C4 C 0.6402(4) 0.2652(3) 0.1761(4) 0.0424(11) Uani 1 1 d . . .
C5 C 0.5186(5) 0.1833(3) 0.1115(3) 0.0422(11) Uani 1 1 d . . .
C6 C 0.3898(4) 0.1204(3) 0.1509(4) 0.0406(11) Uani 1 1 d . . .
C7 C 0.4030(4) 0.1522(3) 0.2640(3) 0.0333(10) Uani 1 1 d . . .
C8 C 0.2783(5) 0.0976(3) 0.3059(3) 0.0351(10) Uani 1 1 d . . .
O1 O 0.7682(3) 0.3673(2) 0.3507(2) 0.0518(8) Uani 1 1 d . . .
O2 O 0.2788(3) 0.0450(2) 0.0928(2) 0.0516(8) Uani 1 1 d . . .
N1 N 0.5377(4) 0.2824(3) 0.5312(3) 0.0549(11) Uani 1 1 d . . .
N2 N 0.1786(4) 0.0553(3) 0.3399(3) 0.0505(10) Uani 1 1 d . . .
C9 C 1.0712(14) 0.2209(9) 0.0209(10) 0.044(3) Uani 0.50 1 d P A 1
C13 C 0.9290(17) 0.1096(10) 0.1682(11) 0.040(3) Uani 0.50 1 d P A 1
N3 N 0.896(2) 0.1557(19) 0.2417(13) 0.067(5) Uani 0.50 1 d P A 1
N4 N 1.124(2) 0.3168(12) 0.0285(15) 0.064(5) Uani 0.50 1 d P A 1
Cl3 Cl 1.1001(6) 0.2799(4) 0.0467(5) 0.0517(10) Uani 0.50 1 d P A 2
Cl4 Cl 0.9341(7) 0.1567(6) 0.2078(4) 0.0537(13) Uani 0.50 1 d P A 2
C10 C 1.0390(5) 0.1201(5) 0.0205(4) 0.0531(13) Uani 1 1 d . . .
C11 C 0.9695(5) 0.0672(5) 0.0879(4) 0.0568(14) Uani 1 1 d . A .
C12 C 0.9302(5) -0.0556(5) 0.0759(4) 0.0608(14) Uani 1 1 d . . .
O3 O 0.8754(3) -0.1014(3) 0.1397(2) 0.0649(10) Uani 1 1 d . A .
N5 N 0.9753(3) 0.7271(2) 0.4023(2) 0.0323(8) Uani 1 1 d . . .
C14 C 0.9426(4) 0.6454(3) 0.4733(3) 0.0360(10) Uani 1 1 d . . .
H14A H 0.9102 0.5678 0.4283 0.043 Uiso 1 1 calc R . .
H14B H 1.0369 0.6581 0.5212 0.043 Uiso 1 1 calc R . .
C15 C 0.8274(4) 0.6513(3) 0.5396(3) 0.0376(10) Uani 1 1 d . . .
H15A H 0.7293 0.6313 0.4933 0.045 Uiso 1 1 calc R . .
H15B H 0.8547 0.7290 0.5832 0.045 Uiso 1 1 calc R . .
C16 C 0.8183(4) 0.5708(3) 0.6097(3) 0.0448(11) Uani 1 1 d . . .
H16A H 0.7971 0.4941 0.5658 0.054 Uiso 1 1 calc R . .
H16B H 0.9155 0.5934 0.6580 0.054 Uiso 1 1 calc R . .
C17 C 0.6991(5) 0.5692(4) 0.6732(4) 0.0638(14) Uani 1 1 d . . .
H17A H 0.7207 0.6448 0.7176 0.096 Uiso 1 1 calc R . .
H17B H 0.6966 0.5165 0.7177 0.096 Uiso 1 1 calc R . .
H17C H 0.6025 0.5453 0.6256 0.096 Uiso 1 1 calc R . .
C18 C 0.8318(4) 0.7212(3) 0.3344(3) 0.0359(10) Uani 1 1 d . . .
H18A H 0.7681 0.7429 0.3812 0.043 Uiso 1 1 calc R . .
H18B H 0.8567 0.7771 0.2919 0.043 Uiso 1 1 calc R . .
C19 C 0.7432(4) 0.6069(3) 0.2608(3) 0.0465(11) Uani 1 1 d . . .
H19A H 0.7191 0.5497 0.3021 0.056 Uiso 1 1 calc R . .
H19B H 0.8037 0.5857 0.2110 0.056 Uiso 1 1 calc R . .
C20 C 0.5984(4) 0.6088(4) 0.1990(4) 0.0605(14) Uani 1 1 d . . .
H20A H 0.5389 0.6318 0.2488 0.073 Uiso 1 1 calc R . .
H20B H 0.6225 0.6646 0.1563 0.073 Uiso 1 1 calc R . .
C21 C 0.5085(6) 0.4937(5) 0.1277(4) 0.107(2) Uani 1 1 d . . .
H21A H 0.5692 0.4694 0.0808 0.161 Uiso 1 1 calc R . .
H21B H 0.4200 0.4976 0.0858 0.161 Uiso 1 1 calc R . .
H21C H 0.4781 0.4397 0.1705 0.161 Uiso 1 1 calc R . .
C22 C 1.0768(4) 0.6921(3) 0.3361(3) 0.0358(10) Uani 1 1 d . . .
H22A H 1.0265 0.6121 0.2978 0.043 Uiso 1 1 calc R . .
H22B H 1.1677 0.6973 0.3837 0.043 Uiso 1 1 calc R . .
C23 C 1.1231(5) 0.7601(3) 0.2567(3) 0.0459(11) Uani 1 1 d . . .
H23A H 1.1770 0.8400 0.2938 0.055 Uiso 1 1 calc R . .
H23B H 1.0335 0.7559 0.2083 0.055 Uiso 1 1 calc R . .
C24 C 1.2236(5) 0.7147(4) 0.1933(4) 0.0545(12) Uani 1 1 d . . .
H24A H 1.2617 0.7659 0.1485 0.065 Uiso 1 1 calc R . .
H24B H 1.3101 0.7160 0.2429 0.065 Uiso 1 1 calc R . .
C25 C 1.1480(5) 0.5959(4) 0.1237(4) 0.0624(13) Uani 1 1 d . . .
H25A H 1.1222 0.5428 0.1679 0.094 Uiso 1 1 calc R . .
H25B H 1.2155 0.5766 0.0804 0.094 Uiso 1 1 calc R . .
H25C H 1.0574 0.5919 0.0781 0.094 Uiso 1 1 calc R . .
C26 C 1.0456(4) 0.8477(3) 0.4681(3) 0.0318(9) Uani 1 1 d . . .
H26A H 0.9783 0.8622 0.5151 0.038 Uiso 1 1 calc R . .
H26B H 1.0515 0.8983 0.4201 0.038 Uiso 1 1 calc R . .
C27 C 1.1995(4) 0.8799(3) 0.5351(3) 0.0374(10) Uani 1 1 d . . .
H27A H 1.2711 0.8724 0.4894 0.045 Uiso 1 1 calc R . .
H27B H 1.1976 0.8288 0.5823 0.045 Uiso 1 1 calc R . .
C28 C 1.2488(4) 1.0022(3) 0.6009(3) 0.0457(11) Uani 1 1 d . . .
H28A H 1.2501 1.0524 0.5530 0.055 Uiso 1 1 calc R . .
H28B H 1.1752 1.0090 0.6451 0.055 Uiso 1 1 calc R . .
C29 C 1.4007(5) 1.0405(4) 0.6709(4) 0.0700(15) Uani 1 1 d . . .
H29A H 1.3997 0.9921 0.7196 0.105 Uiso 1 1 calc R . .
H29B H 1.4264 1.1185 0.7111 0.105 Uiso 1 1 calc R . .
H29C H 1.4746 1.0358 0.6276 0.105 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 0.0000 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'
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
N1 C1 C2 178.8(5) . .
C7 C2 C3 122.5(4) . .
C7 C2 C1 118.9(4) . .
C3 C2 C1 118.6(4) . .
O1 C3 C2 121.8(4) . .
O1 C3 C4 122.6(4) . .
C2 C3 C4 115.6(4) . .
C5 C4 C3 122.3(4) . .
C5 C4 Cl1 121.5(4) . .
C3 C4 Cl1 116.2(3) . .
C4 C5 C6 122.6(4) . .
C4 C5 Cl2 122.3(3) . .
C6 C5 Cl2 115.0(3) . .
O2 C6 C7 121.8(4) . .
O2 C6 C5 123.2(4) . .
C7 C6 C5 115.0(4) . .
C2 C7 C8 120.8(4) . .
C2 C7 C6 122.0(4) . .
C8 C7 C6 117.2(3) . .
N2 C8 C7 179.1(4) . .
N4 C9 C10 169.0(18) . .
N3 C13 C11 175.7(16) . .
C9 C10 C11 127.4(8) . .
C9 C10 C12 110.9(8) . 2_755
C11 C10 C12 121.2(5) . 2_755
C11 C10 Cl3 120.1(5) . .
C12 C10 Cl3 118.7(4) 2_755 .
C13 C11 C10 128.0(8) . .
C13 C11 C12 109.7(8) . .
C10 C11 C12 122.3(6) . .
C10 C11 Cl4 118.0(5) . .
C12 C11 Cl4 119.5(4) . .
O3 C12 C11 121.9(6) . .
O3 C12 C10 121.8(5) . 2_755
C11 C12 C10 116.3(5) . 2_755
C22 N5 C26 112.4(3) . .
C22 N5 C18 111.6(3) . .
C26 N5 C18 106.0(3) . .
C22 N5 C14 105.7(3) . .
C26 N5 C14 110.5(3) . .
C18 N5 C14 110.8(3) . .
C15 C14 N5 117.4(3) . .
C15 C14 H14A 107.9 . .
N5 C14 H14A 107.9 . .
C15 C14 H14B 107.9 . .
N5 C14 H14B 107.9 . .
H14A C14 H14B 107.2 . .
C14 C15 C16 109.7(3) . .
C14 C15 H15A 109.7 . .
C16 C15 H15A 109.7 . .
C14 C15 H15B 109.7 . .
C16 C15 H15B 109.7 . .
H15A C15 H15B 108.2 . .
C17 C16 C15 111.7(3) . .
C17 C16 H16A 109.3 . .
C15 C16 H16A 109.3 . .
C17 C16 H16B 109.3 . .
C15 C16 H16B 109.3 . .
H16A C16 H16B 107.9 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C19 C18 N5 114.9(3) . .
C19 C18 H18A 108.5 . .
N5 C18 H18A 108.5 . .
C19 C18 H18B 108.5 . .
N5 C18 H18B 108.5 . .
H18A C18 H18B 107.5 . .
C18 C19 C20 110.8(3) . .
C18 C19 H19A 109.5 . .
C20 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C20 C19 H19B 109.5 . .
H19A C19 H19B 108.1 . .
C21 C20 C19 110.6(4) . .
C21 C20 H20A 109.5 . .
C19 C20 H20A 109.5 . .
C21 C20 H20B 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 108.1 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N5 C22 C23 115.7(3) . .
N5 C22 H22A 108.4 . .
C23 C22 H22A 108.4 . .
N5 C22 H22B 108.4 . .
C23 C22 H22B 108.4 . .
H22A C22 H22B 107.4 . .
C22 C23 C24 110.4(3) . .
C22 C23 H23A 109.6 . .
C24 C23 H23A 109.6 . .
C22 C23 H23B 109.6 . .
C24 C23 H23B 109.6 . .
H23A C23 H23B 108.1 . .
C25 C24 C23 114.6(4) . .
C25 C24 H24A 108.6 . .
C23 C24 H24A 108.6 . .
C25 C24 H24B 108.6 . .
C23 C24 H24B 108.6 . .
H24A C24 H24B 107.6 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
N5 C26 C27 116.8(3) . .
N5 C26 H26A 108.1 . .
C27 C26 H26A 108.1 . .
N5 C26 H26B 108.1 . .
C27 C26 H26B 108.1 . .
H26A C26 H26B 107.3 . .
C26 C27 C28 109.5(3) . .
C26 C27 H27A 109.8 . .
C28 C27 H27A 109.8 . .
C26 C27 H27B 109.8 . .
C28 C27 H27B 109.8 . .
H27A C27 H27B 108.2 . .
C29 C28 C27 112.8(3) . .
C29 C28 H28A 109.0 . .
C27 C28 H28A 109.0 . .
C29 C28 H28B 109.0 . .
C27 C28 H28B 109.0 . .
H28A C28 H28B 107.8 . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C4 1.716(4) .
Cl2 C5 1.717(5) .
C1 N1 1.154(5) .
C1 C2 1.444(6) .
C2 C7 1.400(5) .
C2 C3 1.435(5) .
C3 O1 1.247(4) .
C3 C4 1.468(6) .
C4 C5 1.360(5) .
C5 C6 1.476(6) .
C6 O2 1.240(4) .
C6 C7 1.451(6) .
C7 C8 1.430(6) .
C8 N2 1.143(5) .
C9 N4 1.160(16) .
C9 C10 1.240(11) .
C13 N3 1.17(2) .
C13 C11 1.263(14) .
Cl3 C10 1.907(7) .
Cl4 C11 1.909(8) .
C10 C11 1.347(6) .
C10 C12 1.499(7) 2_755
C11 C12 1.481(7) .
C12 O3 1.206(5) .
C12 C10 1.499(7) 2_755
N5 C22 1.509(5) .
N5 C26 1.518(5) .
N5 C18 1.527(4) .
N5 C14 1.534(4) .
C14 C15 1.514(5) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.514(5) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.508(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.516(5) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.539(5) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.515(7) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C23 1.519(5) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.538(6) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.521(6) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 C27 1.521(5) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 C28 1.539(5) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C28 C29 1.512(6) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
