#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:07:06 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179880 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/76/7017616.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_7017616
loop_
_publ_author_name
'Gao, Hui'
'Zhang, Xian-Ming'
_publ_section_title
;
 Three novel Bi(iii) complexes with in situ generated anilate ligands:
 unusual oxidation of cyclohexanedione to dihydroxy benzoquinone.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1562
_journal_page_last               1567
_journal_paper_doi               10.1039/c1dt11258a
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C34 H38 Bi2 N4 O24'
_chemical_formula_weight         1304.64
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 112.5330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1663(5)
_cell_length_b                   20.7198(10)
_cell_length_c                   11.3749(5)
_cell_measurement_reflns_used    3349
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.4
_cell_volume                     2213.13(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8865
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        no
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    8.031
_exptl_absorpt_correction_T_max  0.5659
_exptl_absorpt_correction_T_min  0.2120
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'dark red'
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.938
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0358P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                3588
_reflns_number_total             4661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11258a.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7017616
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Bi1 Bi 0.46139(2) 0.903052(9) 0.187655(18) 0.03548(8) Uani 1 1 d .
O1 O 0.4605(4) 0.8046(2) 0.3155(4) 0.0529(11) Uani 1 1 d .
O2 O 0.6990(4) 0.85735(18) 0.3133(4) 0.0494(10) Uani 1 1 d .
O3 O 0.9632(4) 0.68728(19) 0.5609(4) 0.0477(10) Uani 1 1 d .
O4 O 0.7283(4) 0.63464(18) 0.5632(4) 0.0479(10) Uani 1 1 d .
O5 O 1.0397(8) 0.8463(4) 0.5206(8) 0.160(4) Uani 1 1 d .
O6 O 1.0185(5) 0.7880(3) 0.3550(5) 0.0828(15) Uani 1 1 d .
O7 O 0.3643(6) 0.6597(4) 0.3369(6) 0.128(3) Uani 1 1 d .
O8 O 0.4324(5) 0.6850(3) 0.5340(5) 0.0881(18) Uani 1 1 d .
O9 O 0.5918(6) 1.0044(3) 0.3020(6) 0.0929(18) Uani 1 1 d .
O10 O 0.2992(5) 0.9534(2) 0.2900(4) 0.0606(12) Uani 1 1 d .
O11 O 0.3960(4) 1.06569(18) -0.0776(4) 0.0474(10) Uani 1 1 d .
O12 O 0.3502(4) 0.98793(19) 0.0359(4) 0.0481(10) Uani 1 1 d .
C1 C 0.5821(5) 0.7148(3) 0.4340(5) 0.0408(13) Uani 1 1 d .
C2 C 0.5748(6) 0.7745(3) 0.3719(5) 0.0386(13) Uani 1 1 d .
C3 C 0.7129(6) 0.8058(3) 0.3737(5) 0.0394(13) Uani 1 1 d .
C4 C 0.8443(5) 0.7767(3) 0.4407(5) 0.0414(13) Uani 1 1 d .
C5 C 0.8502(5) 0.7177(3) 0.5028(5) 0.0372(12) Uani 1 1 d .
C6 C 0.7130(6) 0.6866(3) 0.5020(5) 0.0388(13) Uani 1 1 d .
C7 C 0.4482(7) 0.6831(3) 0.4281(7) 0.0511(16) Uani 1 1 d .
C8 C 0.9754(6) 0.8084(3) 0.4441(7) 0.0512(16) Uani 1 1 d .
C9 C 0.3084(8) 0.6534(5) 0.5421(8) 0.101(3) Uani 1 1 d .
H9A H 0.3100 0.6582 0.6266 0.151 Uiso 1 1 calc R
H9B H 0.3100 0.6083 0.5229 0.151 Uiso 1 1 calc R
H9C H 0.2233 0.6727 0.4821 0.151 Uiso 1 1 calc R
C10 C 1.1452(8) 0.8167(5) 0.3509(9) 0.109(3) Uani 1 1 d .
H10A H 1.1654 0.7981 0.2823 0.164 Uiso 1 1 calc R
H10B H 1.2237 0.8089 0.4299 0.164 Uiso 1 1 calc R
H10C H 1.1314 0.8624 0.3376 0.164 Uiso 1 1 calc R
C11 C 0.6309(13) 1.1313(6) 0.2534(10) 0.138(4) Uani 1 1 d .
H11A H 0.6737 1.0956 0.2275 0.206 Uiso 1 1 calc R
H11B H 0.7039 1.1602 0.3053 0.206 Uiso 1 1 calc R
H11C H 0.5682 1.1539 0.1794 0.206 Uiso 1 1 calc R
C12 C 0.4821(12) 1.1547(5) 0.3725(10) 0.148(5) Uani 1 1 d .
H12A H 0.4342 1.1334 0.4197 0.222 Uiso 1 1 calc R
H12B H 0.4139 1.1780 0.3027 0.222 Uiso 1 1 calc R
H12C H 0.5513 1.1843 0.4272 0.222 Uiso 1 1 calc R
C13 C 0.5390(9) 1.0473(4) 0.3436(9) 0.100(3) Uani 1 1 d .
C14 C 0.1500(10) 1.0184(7) 0.4115(8) 0.158(6) Uani 1 1 d .
H14A H 0.2465 1.0036 0.4517 0.238 Uiso 1 1 calc R
H14B H 0.0926 0.9985 0.4515 0.238 Uiso 1 1 calc R
H14C H 0.1473 1.0645 0.4200 0.238 Uiso 1 1 calc R
C15 C -0.0501(8) 1.0209(6) 0.2049(9) 0.123(4) Uani 1 1 d .
H15A H -0.0764 1.0071 0.1183 0.185 Uiso 1 1 calc R
H15B H -0.0575 1.0670 0.2073 0.185 Uiso 1 1 calc R
H15C H -0.1126 1.0015 0.2401 0.185 Uiso 1 1 calc R
C16 C 0.1746(8) 0.9719(3) 0.2311(7) 0.0672(19) Uani 1 1 d .
H16A H 0.1349 0.9634 0.1442 0.081 Uiso 1 1 calc R
C17 C 0.4266(5) 1.0157(3) -0.0119(5) 0.0397(13) Uani 1 1 d .
N1 N 0.5518(7) 1.1080(3) 0.3247(5) 0.077(2) Uani 1 1 d .
N2 N 0.0956(6) 1.0015(3) 0.2788(6) 0.0727(18) 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'
Bi Bi -4.1077 10.2566 '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
O11 Bi1 O3 75.04(14) 3_675 4_575
O11 Bi1 O4 116.91(14) 3_675 4_575
O3 Bi1 O4 67.45(12) 4_575 4_575
O11 Bi1 O12 68.49(12) 3_675 .
O3 Bi1 O12 104.52(14) 4_575 .
O4 Bi1 O12 74.19(13) 4_575 .
O11 Bi1 O2 75.35(13) 3_675 .
O3 Bi1 O2 79.37(13) 4_575 .
O4 Bi1 O2 138.34(13) 4_575 .
O12 Bi1 O2 140.86(12) . .
O11 Bi1 O1 132.52(13) 3_675 .
O3 Bi1 O1 73.29(15) 4_575 .
O4 Bi1 O1 81.59(13) 4_575 .
O12 Bi1 O1 154.23(13) . .
O2 Bi1 O1 64.76(12) . .
O11 Bi1 O9 74.83(18) 3_675 .
O3 Bi1 O9 146.69(17) 4_575 .
O4 Bi1 O9 140.94(15) 4_575 .
O12 Bi1 O9 77.02(17) . .
O2 Bi1 O9 79.60(15) . .
O1 Bi1 O9 119.32(17) . .
O11 Bi1 O10 139.86(15) 3_675 .
O3 Bi1 O10 138.73(13) 4_575 .
O4 Bi1 O10 74.80(13) 4_575 .
O12 Bi1 O10 79.79(14) . .
O2 Bi1 O10 123.10(13) . .
O1 Bi1 O10 85.55(14) . .
O9 Bi1 O10 74.58(17) . .
C2 O1 Bi1 119.4(3) . .
C3 O2 Bi1 121.7(3) . .
C5 O3 Bi1 119.9(3) . 4_676
C6 O4 Bi1 119.6(3) . 4_676
C8 O6 C10 117.4(6) . .
C7 O8 C9 118.1(6) . .
C13 O9 Bi1 125.1(6) . .
C16 O10 Bi1 125.2(4) . .
C17 O11 Bi1 119.2(3) . 3_675
C17 O12 Bi1 116.6(3) . .
C6 C1 C2 120.2(5) . .
C6 C1 C7 120.3(5) . .
C2 C1 C7 119.4(5) . .
O1 C2 C1 123.4(5) . .
O1 C2 C3 117.3(5) . .
C1 C2 C3 119.3(5) . .
O2 C3 C4 123.6(5) . .
O2 C3 C2 116.3(5) . .
C4 C3 C2 120.1(5) . .
C3 C4 C5 120.0(5) . .
C3 C4 C8 119.2(5) . .
C5 C4 C8 120.8(5) . .
O3 C5 C4 123.8(5) . .
O3 C5 C6 116.2(5) . .
C4 C5 C6 120.0(5) . .
O4 C6 C1 123.9(5) . .
O4 C6 C5 115.8(5) . .
C1 C6 C5 120.2(5) . .
O7 C7 O8 122.7(7) . .
O7 C7 C1 124.6(7) . .
O8 C7 C1 112.7(6) . .
O5 C8 O6 122.1(7) . .
O5 C8 C4 124.2(7) . .
O6 C8 C4 113.6(6) . .
O8 C9 H9A 109.5 . .
O8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O6 C10 H10A 109.5 . .
O6 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
O6 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 H11A 109.5 . .
N1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N1 C12 H12A 109.5 . .
N1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O9 C13 N1 123.8(11) . .
N2 C14 H14A 109.5 . .
N2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N2 C15 H15A 109.5 . .
N2 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N2 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O10 C16 N2 126.2(7) . .
O10 C16 H16A 116.9 . .
N2 C16 H16A 116.9 . .
O11 C17 O12 126.3(5) . .
O11 C17 C17 117.1(6) . 3_675
O12 C17 C17 116.5(6) . 3_675
C13 N1 C12 120.1(10) . .
C13 N1 C11 122.6(9) . .
C12 N1 C11 117.2(9) . .
C16 N2 C14 120.6(6) . .
C16 N2 C15 123.5(7) . .
C14 N2 C15 115.9(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 O11 2.341(4) 3_675
Bi1 O3 2.367(4) 4_575
Bi1 O4 2.379(4) 4_575
Bi1 O12 2.419(4) .
Bi1 O2 2.476(4) .
Bi1 O1 2.507(4) .
Bi1 O9 2.557(5) .
Bi1 O10 2.576(4) .
O1 C2 1.256(6) .
O2 C3 1.248(6) .
O3 C5 1.253(6) .
O3 Bi1 2.367(4) 4_676
O4 C6 1.259(6) .
O4 Bi1 2.379(4) 4_676
O5 C8 1.169(8) .
O6 C8 1.319(8) .
O6 C10 1.436(8) .
O7 C7 1.166(7) .
O8 C7 1.276(8) .
O8 C9 1.456(8) .
O9 C13 1.224(10) .
O10 C16 1.245(7) .
O11 C17 1.244(6) .
O11 Bi1 2.341(4) 3_675
O12 C17 1.247(6) .
C1 C6 1.386(7) .
C1 C2 1.413(7) .
C1 C7 1.490(8) .
C2 C3 1.540(7) .
C3 C4 1.396(7) .
C4 C5 1.403(7) .
C4 C8 1.472(8) .
C5 C6 1.533(7) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N1 1.428(11) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 N1 1.424(11) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 N1 1.291(11) .
C14 N2 1.438(9) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 N2 1.452(8) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 N2 1.284(8) .
C16 H16A 0.9300 .
C17 C17 1.555(11) 3_675
