#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:06:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/64/4336452.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_4336452
loop_
_publ_author_name
'Pauline J. Han'
'Arnold L. Rheingold'
'William C. Trogler'
_publ_section_title
;
 Luminescent Tris(8-hydroxyquinolates) of Bismuth(III)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12033
_journal_page_last               12045
_journal_paper_doi               10.1021/ic401850v
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C31 H23 Bi Br3 N3 O4'
_chemical_formula_weight         950.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   40.5434(17)
_cell_length_b                   40.5434(17)
_cell_length_c                   11.0916(4)
_cell_measurement_reflns_used    9036
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.39
_cell_volume                     15789.4(11)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45033
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    8.477
_exptl_absorpt_correction_T_max  0.2459
_exptl_absorpt_correction_T_min  0.1663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_description       block
_exptl_crystal_F_000             8100
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_platon_squeeze_details
; 
 SQUEEZE (PLATON, A. Spek) was used to treat diffuse solvent 
 contributions.  Total electron count found = 419/unit cell (in 
 three equal vol.).  Calculated for 12 THF (the re'xtal solvent) 
 = 480/unit cell.  The intensive properties (density, F(000), 
 etc.) reflect these contributions.
;
_refine_diff_density_max         1.563
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6405
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      2.169
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0340P)²+188.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                5605
_reflns_number_total             6405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401850v_si_002_3.cif
_cod_data_source_block           trog41
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4336452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.319855(12) 0.121692(11) 0.08871(4) 0.02767(17) Uani 1 1 d .
Br1 Br 0.22067(4) 0.14818(4) 0.32581(14) 0.0494(4) Uani 1 1 d .
Br2 Br 0.29405(3) 0.23624(3) 0.00345(10) 0.0308(3) Uani 1 1 d .
Br3 Br 0.33642(3) 0.01766(3) -0.16342(10) 0.0313(3) Uani 1 1 d .
O1 O 0.2764(2) 0.1280(2) 0.2102(7) 0.0303(18) Uani 1 1 d .
O2 O 0.3096(2) 0.1702(2) 0.0289(7) 0.0286(17) Uani 1 1 d .
O3 O 0.3230(2) 0.0730(2) -0.0122(7) 0.0283(17) Uani 1 1 d .
O4 O 0.1833(9) 0.1656(8) -0.090(3) 0.198(11) Uiso 1 1 d D
N1 N 0.2775(3) 0.0622(3) 0.2212(8) 0.028(2) Uani 1 1 d .
N2 N 0.3489(3) 0.1492(3) -0.1201(8) 0.029(2) Uani 1 1 d .
N3 N 0.2648(3) 0.0874(3) -0.0268(8) 0.027(2) Uani 1 1 d .
C1 C 0.2783(3) 0.0300(3) 0.2248(10) 0.032(3) Uani 1 1 d .
H1A H 0.2947 0.0266 0.1713 0.038 Uiso 1 1 calc R
C2 C 0.2557(4) 0.0008(3) 0.3055(11) 0.037(3) Uani 1 1 d .
H2A H 0.2569 -0.0220 0.3068 0.045 Uiso 1 1 calc R
C3 C 0.2320(4) 0.0050(4) 0.3814(11) 0.041(3) Uani 1 1 d .
H3A H 0.2170 -0.0146 0.4372 0.049 Uiso 1 1 calc R
C4 C 0.2293(4) 0.0380(3) 0.3783(11) 0.034(3) Uani 1 1 d .
C5 C 0.2039(4) 0.0439(4) 0.4515(12) 0.042(3) Uani 1 1 d .
H5A H 0.1886 0.0255 0.5103 0.050 Uiso 1 1 calc R
C6 C 0.2017(4) 0.0771(4) 0.4359(11) 0.040(3) Uani 1 1 d .
H6A H 0.1841 0.0810 0.4817 0.048 Uiso 1 1 calc R
C7 C 0.2259(4) 0.1046(4) 0.3512(12) 0.037(3) Uani 1 1 d .
C8 C 0.2529(3) 0.1015(3) 0.2829(10) 0.029(2) Uani 1 1 d .
C9 C 0.2533(3) 0.0667(3) 0.2954(10) 0.030(2) Uani 1 1 d .
C10 C 0.3688(3) 0.1396(3) -0.1895(10) 0.031(3) Uani 1 1 d .
H10A H 0.3692 0.1169 -0.1711 0.038 Uiso 1 1 calc R
C11 C 0.3898(4) 0.1612(3) -0.2905(11) 0.035(3) Uani 1 1 d .
H11A H 0.4039 0.1531 -0.3384 0.042 Uiso 1 1 calc R
C12 C 0.3895(3) 0.1940(3) -0.3182(10) 0.033(3) Uani 1 1 d .
H12A H 0.4034 0.2090 -0.3855 0.040 Uiso 1 1 calc R
C13 C 0.3680(3) 0.2053(3) -0.2455(10) 0.030(2) Uani 1 1 d .
C14 C 0.3658(3) 0.2385(3) -0.2673(10) 0.032(3) Uani 1 1 d .
H14A H 0.3793 0.2547 -0.3331 0.038 Uiso 1 1 calc R
C15 C 0.3443(3) 0.2472(3) -0.1933(10) 0.031(3) Uani 1 1 d .
H15A H 0.3430 0.2696 -0.2075 0.037 Uiso 1 1 calc R
C16 C 0.3240(3) 0.2232(3) -0.0967(10) 0.027(2) Uani 1 1 d .
C17 C 0.3260(3) 0.1911(3) -0.0673(10) 0.028(2) Uani 1 1 d .
C18 C 0.3481(3) 0.1820(3) -0.1467(10) 0.027(2) Uani 1 1 d .
C19 C 0.2367(4) 0.0954(4) -0.0298(11) 0.036(3) Uani 1 1 d .
H19A H 0.2382 0.1154 0.0188 0.043 Uiso 1 1 calc R
C20 C 0.2050(4) 0.0747(4) -0.1035(12) 0.042(3) Uani 1 1 d .
H20A H 0.1849 0.0803 -0.1036 0.051 Uiso 1 1 calc R
C21 C 0.2028(4) 0.0464(4) -0.1751(12) 0.041(3) Uani 1 1 d .
H21A H 0.1813 0.0326 -0.2260 0.050 Uiso 1 1 calc R
C22 C 0.2324(3) 0.0374(3) -0.1742(10) 0.032(3) Uani 1 1 d .
C23 C 0.2330(3) 0.0094(3) -0.2472(10) 0.033(3) Uani 1 1 d .
H23A H 0.2125 -0.0051 -0.3010 0.040 Uiso 1 1 calc R
C24 C 0.2632(3) 0.0030(3) -0.2410(10) 0.031(3) Uani 1 1 d .
H24A H 0.2633 -0.0163 -0.2893 0.037 Uiso 1 1 calc R
C25 C 0.2937(3) 0.0248(3) -0.1635(9) 0.027(2) Uani 1 1 d .
C27 C 0.2632(3) 0.0588(3) -0.0949(10) 0.027(2) Uani 1 1 d .
C26 C 0.2950(3) 0.0528(3) -0.0863(9) 0.026(2) Uani 1 1 d .
C28 C 0.1406(13) 0.1518(14) -0.142(4) 0.23(2) Uiso 1 1 d D
H28A H 0.1220 0.1471 -0.0767 0.277 Uiso 1 1 calc R
H28B H 0.1402 0.1695 -0.2023 0.277 Uiso 1 1 calc R
C29 C 0.1353(13) 0.1142(18) -0.199(6) 0.43(5) Uiso 1 1 d D
H29A H 0.1338 0.0959 -0.1369 0.510 Uiso 1 1 calc R
H29B H 0.1125 0.1018 -0.2513 0.510 Uiso 1 1 calc R
C30 C 0.1714(17) 0.1304(16) -0.270(4) 0.30(3) Uiso 1 1 d D
H30A H 0.1760 0.1100 -0.2999 0.358 Uiso 1 1 calc R
H30B H 0.1709 0.1455 -0.3393 0.358 Uiso 1 1 calc R
C31 C 0.2007(12) 0.1550(19) -0.179(6) 0.36(4) Uiso 1 1 d D
H31A H 0.2122 0.1409 -0.1424 0.433 Uiso 1 1 calc R
H31B H 0.2212 0.1780 -0.2194 0.433 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'
Br Br -0.2901 2.4595 '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_3
O2 Bi1 O3 134.1(3) .
O2 Bi1 O1 66.6(3) .
O3 Bi1 O1 137.4(3) .
O2 Bi1 N3 79.8(3) .
O3 Bi1 N3 70.9(3) .
O1 Bi1 N3 80.4(3) .
O2 Bi1 N2 67.1(3) .
O3 Bi1 N2 74.3(3) .
O1 Bi1 N2 132.5(3) .
N3 Bi1 N2 81.9(3) .
O2 Bi1 N1 129.5(3) .
O3 Bi1 N1 77.1(3) .
O1 Bi1 N1 65.9(3) .
N3 Bi1 N1 76.6(3) .
N2 Bi1 N1 148.5(3) .
O2 Bi1 Bi1 51.60(19) 13
O3 Bi1 Bi1 162.38(19) 13
O1 Bi1 Bi1 58.97(19) 13
N3 Bi1 Bi1 124.8(2) 13
N2 Bi1 Bi1 98.5(2) 13
N1 Bi1 Bi1 112.6(2) 13
C8 O1 Bi1 123.3(7) .
C17 O2 Bi1 122.2(7) .
C26 O3 Bi1 115.9(7) .
C31 O4 C28 105(2) .
C1 N1 C9 119.2(10) .
C1 N1 Bi1 126.9(8) .
C9 N1 Bi1 113.9(7) .
C10 N2 C18 118.5(10) .
C10 N2 Bi1 127.9(8) .
C18 N2 Bi1 112.5(7) .
C19 N3 C27 120.8(10) .
C19 N3 Bi1 123.3(8) .
C27 N3 Bi1 115.8(7) .
N1 C1 C2 121.6(11) .
C3 C2 C1 120.0(11) .
C2 C3 C4 120.5(12) .
C3 C4 C9 116.8(11) .
C3 C4 C5 123.8(12) .
C9 C4 C5 119.4(11) .
C6 C5 C4 119.3(12) .
C5 C6 C7 119.2(11) .
C8 C7 C6 124.0(11) .
C8 C7 Br1 117.5(9) .
C6 C7 Br1 118.5(9) .
O1 C8 C7 123.3(10) .
O1 C8 C9 120.8(10) .
C7 C8 C9 115.9(11) .
N1 C9 C4 122.0(10) .
N1 C9 C8 116.0(10) .
C4 C9 C8 122.0(11) .
N2 C10 C11 123.5(11) .
C12 C11 C10 118.8(11) .
C11 C12 C13 119.3(11) .
C18 C13 C14 119.0(10) .
C18 C13 C12 117.6(10) .
C14 C13 C12 123.4(10) .
C15 C14 C13 119.7(11) .
C14 C15 C16 120.5(11) .
C17 C16 C15 122.8(10) .
C17 C16 Br2 118.0(8) .
C15 C16 Br2 119.1(8) .
O2 C17 C16 123.2(10) .
O2 C17 C18 120.9(10) .
C16 C17 C18 115.9(10) .
N2 C18 C13 122.1(10) .
N2 C18 C17 115.9(10) .
C13 C18 C17 121.9(10) .
N3 C19 C20 120.8(12) .
C21 C20 C19 120.1(12) .
C20 C21 C22 120.4(12) .
C23 C22 C27 119.0(11) .
C23 C22 C21 124.3(11) .
C27 C22 C21 116.7(11) .
C24 C23 C22 120.1(11) .
C23 C24 C25 120.1(11) .
C24 C25 C26 123.4(11) .
C24 C25 Br3 119.4(8) .
C26 C25 Br3 117.2(8) .
N3 C27 C22 121.2(10) .
N3 C27 C26 116.5(10) .
C22 C27 C26 122.2(10) .
O3 C26 C25 124.2(10) .
O3 C26 C27 120.7(10) .
C25 C26 C27 115.1(10) .
C29 C28 O4 95(3) .
C30 C29 C28 99(3) .
C31 C30 C29 102.4(17) .
O4 C31 C30 109(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 O2 2.303(7) .
Bi1 O3 2.328(7) .
Bi1 O1 2.331(7) .
Bi1 N3 2.335(9) .
Bi1 N2 2.585(9) .
Bi1 N1 2.603(9) .
Bi1 Bi1 3.6743(8) 13
Br1 C7 1.902(12) .
Br2 C16 1.904(11) .
Br3 C25 1.893(11) .
O1 C8 1.300(14) .
O2 C17 1.316(13) .
O3 C26 1.305(13) .
O4 C31 1.40(6) .
O4 C28 1.63(5) .
N1 C1 1.325(14) .
N1 C9 1.359(15) .
N2 C10 1.309(14) .
N2 C18 1.376(14) .
N3 C19 1.332(15) .
N3 C27 1.360(14) .
C1 C2 1.399(17) .
C2 C3 1.350(18) .
C3 C4 1.394(17) .
C4 C9 1.419(16) .
C4 C5 1.422(18) .
C5 C6 1.403(18) .
C6 C7 1.413(18) .
C7 C8 1.387(17) .
C8 C9 1.429(15) .
C10 C11 1.414(17) .
C11 C12 1.374(17) .
C12 C13 1.419(16) .
C13 C18 1.410(16) .
C13 C14 1.413(16) .
C14 C15 1.368(16) .
C15 C16 1.404(16) .
C16 C17 1.385(15) .
C17 C18 1.430(16) .
C19 C20 1.395(18) .
C20 C21 1.360(19) .
C21 C22 1.418(18) .
C22 C23 1.405(17) .
C22 C27 1.416(16) .
C23 C24 1.375(17) .
C24 C25 1.400(16) .
C25 C26 1.401(15) .
C27 C26 1.429(16) .
C28 C29 1.56(7) .
C29 C30 1.50(2) .
C30 C31 1.49(2) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 -0.007 1089 140
2 0.333 0.667 0.497 1090 139
3 0.667 0.333 0.164 1090 140
