#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:18:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178844 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/98/4109817.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_4109817
loop_
_publ_author_name
'Victor I. Ovcharenko'
'Elena V. Gorelik'
'Sergey V. Fokin'
'Galina V. Romanenko'
'Vladimir N. Ikorskii'
'Anna V. Krashilina'
'Vladimir K. Cherkasov'
'Gleb A. Abakumov'
_publ_section_title
;
 Ligand Effects on the Ferro- to Antiferromagnetic Exchange Ratio in
 Bis(o-Semiquinonato)copper(II)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10512
_journal_page_last               10521
_journal_paper_doi               10.1021/ja072463b
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'Cu(C10 H10 O2)2 ((C2 H5)2 O) (C5 H5 N)'
_chemical_formula_sum            'C37 H55 Cu N O5'
_chemical_formula_weight         657.36
_chemical_name_systematic
; 
 [bis(3,6-di-tert-butyl-o-benzosemiquinonato)(pyridine)copper(II)] ester solvate
;
_space_group_IT_number           6
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2y'
_symmetry_space_group_name_H-M   'P 1 m 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                 90.073(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3410(17)
_cell_length_b                   17.855(3)
_cell_length_c                   10.3418(17)
_cell_measurement_reflns_used    5561
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.17
_cell_measurement_theta_min      2.28
_cell_volume                     1909.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14832
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_meas      0
_exptl_crystal_description       'distorted octahedron '
_exptl_crystal_F_000             706
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_coef       0.0000(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         5700
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          10.159
_refine_ls_shift/su_mean         0.217
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                5354
_reflns_number_total             5700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja072463bsi20070522_080040_3.cif
_cod_data_source_block           nnn
_cod_database_code               4109817
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
Cu1 Cu 0.1738 0.5000 0.7121 0.0538(3) Uani 1 2 d S
O11 O 0.1013(5) 0.41949(19) 0.8157(5) 0.0506(11) Uani 1 1 d .
C11 C 0.1411(6) 0.3551(3) 0.7802(6) 0.0346(13) Uani 1 1 d .
C12 C 0.0999(6) 0.2865(2) 0.8367(6) 0.0324(11) Uani 1 1 d .
C13 C -0.0078(7) 0.2872(3) 0.9394(8) 0.0472(15) Uani 1 1 d .
C131 C -0.0392(9) 0.2076(4) 0.9851(10) 0.067(2) Uani 1 1 d .
H13A H -0.0722 0.1789 0.9138 0.06(2) Uiso 1 1 calc R
H13B H -0.1030 0.2096 1.0523 0.08(2) Uiso 1 1 calc R
H13C H 0.0379 0.1843 1.0177 0.024(16) Uiso 1 1 calc R
C132 C 0.0415(10) 0.3299(5) 1.0582(9) 0.073(3) Uani 1 1 d .
H13D H 0.0631 0.3803 1.0338 0.08(3) Uiso 1 1 calc R
H13E H 0.1170 0.3054 1.0918 0.09(3) Uiso 1 1 calc R
H13F H -0.0246 0.3309 1.1232 0.11(4) Uiso 1 1 calc R
C133 C -0.1307(8) 0.3235(6) 0.8844(12) 0.076(3) Uani 1 1 d .
H13G H -0.1598 0.2954 0.8108 0.07(3) Uiso 1 1 calc R
H13H H -0.1121 0.3740 0.8586 0.07(2) Uiso 1 1 calc R
H13I H -0.1969 0.3237 0.9493 0.09(3) Uiso 1 1 calc R
C14 C 0.1548(7) 0.2241(3) 0.7875(7) 0.0362(12) Uani 1 1 d .
H14A H 0.1263 0.1781 0.8184 0.051(15) Uiso 1 1 calc R
C15 C 0.2524(7) 0.2239(3) 0.6926(7) 0.0356(13) Uani 1 1 d .
H15A H 0.2866 0.1782 0.6665 0.038(13) Uiso 1 1 calc R
C16 C 0.2986(6) 0.2872(3) 0.6378(7) 0.0350(11) Uani 1 1 d .
C17 C 0.4070(7) 0.2881(3) 0.5327(8) 0.0451(14) Uani 1 1 d .
C171 C 0.4479(9) 0.2088(4) 0.4948(10) 0.0652(19) Uani 1 1 d .
H17A H 0.5132 0.2113 0.4289 0.046(18) Uiso 1 1 calc R
H17B H 0.3743 0.1819 0.4624 0.06(3) Uiso 1 1 calc R
H17C H 0.4820 0.1834 0.5692 0.12(5) Uiso 1 1 calc R
C172 C 0.5231(8) 0.3306(5) 0.5824(10) 0.068(3) Uani 1 1 d .
H17D H 0.5890 0.3315 0.5170 0.047(19) Uiso 1 1 calc R
H17E H 0.5561 0.3064 0.6584 0.11(4) Uiso 1 1 calc R
H17F H 0.4982 0.3810 0.6032 0.08(3) Uiso 1 1 calc R
C173 C 0.3498(10) 0.3242(6) 0.4090(9) 0.070(3) Uani 1 1 d .
H17G H 0.4145 0.3251 0.3425 0.05(2) Uiso 1 1 calc R
H17H H 0.3226 0.3744 0.4278 0.13(4) Uiso 1 1 calc R
H17I H 0.2770 0.2953 0.3801 0.14(5) Uiso 1 1 calc R
C18 C 0.2420(6) 0.3565(3) 0.6822(6) 0.0329(13) Uani 1 1 d .
O12 O 0.2764(5) 0.4205(2) 0.6380(5) 0.0495(12) Uani 1 1 d .
N11S N 0.0179(9) 0.5000 0.5538(11) 0.071(2) Uani 1 2 d S
C11S C -0.1017(17) 0.5000 0.580(2) 0.110(6) Uani 1 2 d S
H11A H -0.1246 0.5000 0.6672 0.06(3) Uiso 1 2 calc SR
C12S C -0.203(2) 0.5000 0.489(4) 0.164(12) Uani 1 2 d S
H12A H -0.2873 0.5000 0.5191 2(3) Uiso 1 2 calc SR
C13S C -0.185(3) 0.5000 0.374(2) 0.126(7) Uani 1 2 d S
H13J H -0.2530 0.5000 0.3151 2(3) Uiso 1 2 calc SR
C14S C -0.043(4) 0.5000 0.328(2) 0.172(13) Uani 1 2 d S
H14B H -0.0211 0.5000 0.2414 0.13(6) Uiso 1 2 calc SR
C15S C 0.0553(17) 0.5000 0.4328(13) 0.093(5) Uani 1 2 d S
H15B H 0.1429 0.5000 0.4124 2(3) Uiso 1 2 calc SR
Cu2 Cu -0.27152(13) 0.0000 0.21208(13) 0.0530(3) Uani 1 2 d S
O21 O -0.1995(5) 0.08044(19) 0.3164(5) 0.0498(11) Uani 1 1 d .
C21 C -0.2421(6) 0.1444(3) 0.2809(7) 0.0367(13) Uani 1 1 d .
C22 C -0.1978(6) 0.2137(3) 0.3366(7) 0.0351(11) Uani 1 1 d .
C23 C -0.0914(7) 0.2127(3) 0.4400(8) 0.0469(15) Uani 1 1 d .
C231 C -0.0586(10) 0.2929(4) 0.4844(11) 0.072(3) Uani 1 1 d .
H23B H -0.0265 0.3212 0.4124 0.038(19) Uiso 1 1 calc R
H23C H 0.0061 0.2910 0.5509 0.10(3) Uiso 1 1 calc R
H23D H -0.1351 0.3165 0.5177 0.07(3) Uiso 1 1 calc R
C233 C -0.1386(10) 0.1698(6) 0.5595(9) 0.072(3) Uani 1 1 d .
H23E H -0.2157 0.1930 0.5922 0.09(3) Uiso 1 1 calc R
H23F H -0.0727 0.1708 0.6250 0.14(5) Uiso 1 1 calc R
H23G H -0.1568 0.1189 0.5362 0.10(3) Uiso 1 1 calc R
C232 C 0.0325(8) 0.1760(6) 0.3830(11) 0.073(3) Uani 1 1 d .
H23H H 0.0613 0.2044 0.3097 0.09(3) Uiso 1 1 calc R
H23I H 0.0133 0.1257 0.3565 0.08(3) Uiso 1 1 calc R
H23J H 0.0992 0.1753 0.4476 0.08(3) Uiso 1 1 calc R
C24 C -0.2522(7) 0.2759(3) 0.2871(7) 0.0362(12) Uani 1 1 d .
H24D H -0.2236 0.3219 0.3182 0.057(16) Uiso 1 1 calc R
C25 C -0.3486(7) 0.2763(3) 0.1924(8) 0.0373(13) Uani 1 1 d .
H25A H -0.3819 0.3222 0.1660 0.035(12) Uiso 1 1 calc R
C26 C -0.3963(6) 0.2130(3) 0.1367(7) 0.0347(11) Uani 1 1 d .
C27 C -0.5043(7) 0.2117(3) 0.0329(8) 0.0450(14) Uani 1 1 d .
C273 C -0.5470(9) 0.2911(3) -0.0040(10) 0.0631(19) Uani 1 1 d .
H27A H -0.5815 0.3159 0.0707 0.13(5) Uiso 1 1 calc R
H27B H -0.6123 0.2884 -0.0699 0.029(14) Uiso 1 1 calc R
H27C H -0.4740 0.3186 -0.0360 0.06(3) Uiso 1 1 calc R
C272 C -0.4494(9) 0.1758(6) -0.0917(9) 0.071(3) Uani 1 1 d .
H27D H -0.5154 0.1746 -0.1570 0.05(2) Uiso 1 1 calc R
H27E H -0.4214 0.1256 -0.0733 0.10(3) Uiso 1 1 calc R
H27F H -0.3773 0.2048 -0.1219 0.12(4) Uiso 1 1 calc R
C271 C -0.6205(8) 0.1690(6) 0.0843(11) 0.072(3) Uani 1 1 d .
H27G H -0.6524 0.1932 0.1607 0.11(4) Uiso 1 1 calc R
H27H H -0.5953 0.1186 0.1049 0.10(3) Uiso 1 1 calc R
H27I H -0.6872 0.1680 0.0197 0.046(19) Uiso 1 1 calc R
C28 C -0.3440(7) 0.1440(3) 0.1832(7) 0.0324(13) Uani 1 1 d .
O22 O -0.3749(5) 0.07961(19) 0.1384(5) 0.0491(12) Uani 1 1 d .
N21S N -0.1150(9) 0.0000 0.0539(10) 0.069(2) Uani 1 2 d S
C21S C -0.1468(15) 0.0000 -0.0652(12) 0.086(4) Uani 1 2 d S
H21A H -0.2343 0.0000 -0.0858 1.8(6) Uiso 1 2 calc SR
C22S C -0.054(3) 0.0000 -0.171(3) 0.176(11) Uani 1 2 d S
H22A H -0.0784 0.0000 -0.2572 0.14(7) Uiso 1 2 calc SR
C23S C 0.083(3) 0.0000 -0.129(2) 0.135(8) Uani 1 2 d S
H23A H 0.1510 0.0000 -0.1880 0.04(2) Uiso 1 2 calc SR
C24S C 0.1022(19) 0.0000 -0.004(4) 0.175(14) Uani 1 2 d S
H24A H 0.1883 0.0000 0.0224 0.9(11) Uiso 1 2 calc SR
C25S C 0.0110(14) 0.0000 0.097(2) 0.107(6) Uani 1 2 d S
H25B H 0.0293 0.0000 0.1478 0(2) Uiso 1 2 d SR
C21A C -0.681(3) 0.5000 0.045(3) 0.188(12) Uani 1 2 d SD
C22A C -0.600(4) 0.5000 0.171(3) 0.46(6) Uani 1 2 d SD
O21A O -0.503(3) 0.5000 0.069(3) 0.32(2) Uani 1 2 d SD
C23A C -0.527(3) 0.5000 -0.074(3) 0.197(17) Uani 1 2 d SD
C24A C -0.381(4) 0.5000 -0.123(5) 0.62(12) Uani 1 2 d SD
C11A C 0.588(4) 0.0000 0.581(5) 0.42(4) Uani 1 2 d SD
O11A O 0.415(3) 0.0000 0.600(3) 0.43(3) Uani 1 2 d SD
C12A C 0.482(6) 0.0000 0.475(3) 0.39(5) Uani 1 2 d SD
C13A C 0.290(6) 0.0000 0.535(5) 0.85(15) Uani 1 2 d SD
C14A C 0.314(11) 0.0000 0.387(5) 0.55(10) Uani 1 2 d SD
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'
Cu Cu 0.3201 1.2651 '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
O12 Cu1 O12 94.6(2) 2_565 .
O12 Cu1 O11 83.53(11) 2_565 2_565
O12 Cu1 O11 167.09(18) . 2_565
O12 Cu1 O11 167.09(18) 2_565 .
O12 Cu1 O11 83.53(11) . .
O11 Cu1 O11 95.4(2) 2_565 .
O12 Cu1 N11S 95.9(3) 2_565 .
O12 Cu1 N11S 95.9(3) . .
O11 Cu1 N11S 97.0(3) 2_565 .
O11 Cu1 N11S 97.0(3) . .
C11 O11 Cu1 112.5(3) . .
O11 C11 C12 124.1(5) . .
O11 C11 C18 114.7(5) . .
C12 C11 C18 121.1(5) . .
C14 C12 C11 115.4(4) . .
C14 C12 C13 124.8(4) . .
C11 C12 C13 119.6(4) . .
C12 C13 C133 110.3(7) . .
C12 C13 C131 111.0(4) . .
C133 C13 C131 109.2(8) . .
C12 C13 C132 108.5(6) . .
C133 C13 C132 111.2(6) . .
C131 C13 C132 106.6(8) . .
C12 C14 C15 124.5(5) . .
C16 C15 C14 123.0(5) . .
C15 C16 C18 116.1(5) . .
C15 C16 C17 123.7(4) . .
C18 C16 C17 120.2(4) . .
C172 C17 C171 109.4(7) . .
C172 C17 C173 112.0(6) . .
C171 C17 C173 106.2(8) . .
C172 C17 C16 109.8(7) . .
C171 C17 C16 111.5(5) . .
C173 C17 C16 107.8(6) . .
O12 C18 C16 122.6(5) . .
O12 C18 C11 117.6(5) . .
C16 C18 C11 119.9(5) . .
C18 O12 Cu1 111.2(3) . .
C11S N11S C15S 119.7(12) . .
C11S N11S Cu1 122.1(12) . .
C15S N11S Cu1 118.2(9) . .
N11S C11S C12S 125(2) . .
C13S C12S C11S 123(3) . .
C12S C13S C14S 117(2) . .
C15S C14S C13S 115.7(19) . .
N11S C15S C14S 119.4(18) . .
O22 Cu2 O22 94.6(2) 2 .
O22 Cu2 O21 166.55(18) 2 .
O22 Cu2 O21 83.50(11) . .
O22 Cu2 O21 83.50(11) 2 2
O22 Cu2 O21 166.55(18) . 2
O21 Cu2 O21 95.3(2) . 2
O22 Cu2 N21S 96.2(3) 2 .
O22 Cu2 N21S 96.2(3) . .
O21 Cu2 N21S 97.2(3) . .
O21 Cu2 N21S 97.2(3) 2 .
C21 O21 Cu2 111.7(3) . .
O21 C21 C22 123.0(5) . .
O21 C21 C28 116.2(5) . .
C22 C21 C28 120.7(5) . .
C24 C22 C21 115.1(4) . .
C24 C22 C23 125.1(4) . .
C21 C22 C23 119.7(4) . .
C232 C23 C231 108.9(7) . .
C232 C23 C22 109.3(7) . .
C231 C23 C22 110.8(4) . .
C232 C23 C233 110.9(6) . .
C231 C23 C233 107.1(8) . .
C22 C23 C233 109.8(6) . .
C22 C24 C25 124.7(5) . .
C26 C25 C24 123.4(5) . .
C25 C26 C28 115.9(4) . .
C25 C26 C27 124.5(4) . .
C28 C26 C27 119.6(4) . .
C271 C27 C273 108.9(7) . .
C271 C27 C272 111.9(6) . .
C273 C27 C272 106.4(8) . .
C271 C27 C26 109.6(7) . .
C273 C27 C26 111.5(4) . .
C272 C27 C26 108.5(6) . .
O22 C28 C26 123.9(5) . .
O22 C28 C21 115.8(5) . .
C26 C28 C21 120.1(5) . .
C28 O22 Cu2 112.3(3) . .
C21S N21S C25S 123.6(11) . .
C21S N21S Cu2 120.4(8) . .
C25S N21S Cu2 116.0(11) . .
N21S C21S C22S 123.7(17) . .
C21S C22S C23S 115(2) . .
C24S C23S C22S 115(2) . .
C23S C24S C25S 129(2) . .
N21S C25S C24S 114(2) . .
C21A C22A O21A 76(2) . .
C22A O21A C23A 127(2) . .
O21A C23A C24A 99.0(15) . .
C12A O11A C13A 91(5) . .
O11A C12A C11A 73(2) . .
C14A C13A O11A 108(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O12 1.932(4) 2_565
Cu1 O12 1.932(4) .
Cu1 O11 1.943(4) 2_565
Cu1 O11 1.943(4) .
Cu1 N11S 2.296(8) .
O11 C11 1.275(6) .
C11 C12 1.423(7) .
C11 C18 1.456(6) .
C12 C14 1.351(7) .
C12 C13 1.540(8) .
C13 C133 1.535(13) .
C13 C131 1.534(8) .
C13 C132 1.532(13) .
C14 C15 1.408(7) .
C15 C16 1.352(7) .
C16 C18 1.444(7) .
C16 C17 1.563(7) .
C17 C172 1.510(12) .
C17 C171 1.530(8) .
C17 C173 1.548(13) .
C18 O12 1.280(6) .
N11S C11S 1.27(2) .
N11S C15S 1.311(17) .
C11S C12S 1.41(3) .
C12S C13S 1.21(4) .
C13S C14S 1.53(4) .
C14S C15S 1.48(3) .
Cu2 O22 1.935(3) 2
Cu2 O22 1.935(3) .
Cu2 O21 1.944(3) .
Cu2 O21 1.944(3) 2
Cu2 N21S 2.303(8) .
O21 C21 1.278(6) .
C21 C22 1.439(7) .
C21 C28 1.459(6) .
C22 C24 1.345(7) .
C22 C23 1.534(7) .
C23 C232 1.556(13) .
C23 C231 1.541(8) .
C23 C233 1.534(12) .
C24 C25 1.397(7) .
C25 C26 1.361(7) .
C26 C28 1.428(7) .
C26 C27 1.548(7) .
C27 C271 1.521(13) .
C27 C273 1.532(8) .
C27 C272 1.548(13) .
C28 O22 1.281(6) .
N21S C21S 1.274(16) .
N21S C25S 1.375(18) .
C21S C22S 1.46(3) .
C22S C23S 1.48(4) .
C23S C24S 1.31(4) .
C24S C25S 1.40(4) .
C21A C22A 1.55(2) .
C22A O21A 1.45(2) .
O21A C23A 1.500(18) .
C23A C24A 1.596(19) .
C11A C12A 1.55(2) .
O11A C12A 1.461(19) .
O11A C13A 1.46(2) .
C13A C14A 1.55(3) .
