# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_k13mfm4
_database_code_depnum_ccdc_archive 'CCDC 1051714'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16.50 H15.50 Bi N1.50 O6.50'
_chemical_formula_weight         547.78

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbna

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x, y-1/2, z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1350(2)
_cell_length_b                   19.2390(5)
_cell_length_c                   23.2510(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3191.67(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    94479
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080
_exptl_absorpt_coefficient_mu    11.089
# Absorption correction 

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.294
_exptl_absorpt_correction_T_max  0.346
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45367
_diffrn_reflns_av_R_equivalents  0.1311
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2818
_reflns_number_gt                1989
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The asymmetric unit consists of one bismuth, 1 deferiprone ligand, 1 BDC ligand
and a small amount of residual solvent.
All atoms in the DFP ligand are disordered in a 50:50 ratio over 2 sites.
Fractional occupancy atoms were refined anisotropically, but with some ADP 
restraints, in order to assist convergence.
Residual electron density approximates to 1/2 of a molecule of DMF per 
bismuth, and allowance has been made for this in the formula presented. 

The latter could not be treated using squeeze, as the solvent accessible 
regions coincide with the disordered deferiprone fragment. As such - SQUEEZE
see no solvent accessible voids. Using the algorithm without one set of the 
disordered ligand atoms served to give an estimate of the volume however.
This estimate, couple with the residual electron density maxima in that region
were used to make the guest solvent estimate.

The crystal was of 'adequate' quality here, but not of 'rolls-royce' calibre.
The highest residual maximum is at a chemically insignificant distance from
the bismuth centre.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0407P)²+49.1677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     284
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Bi1 Bi 0.58335(5) 0.10293(2) 0.713637(16) 0.01992(15) Uani 1 1 d . . .
O1 O 0.5886(10) 0.2342(4) 0.6837(3) 0.0274(17) Uani 1 1 d . . .
O2 O 0.8468(11) 0.1743(4) 0.7031(3) 0.0266(19) Uani 1 1 d . . .
O3 O 1.1475(10) 0.5329(4) 0.7045(3) 0.0245(18) Uani 1 1 d . . .
O4 O 1.4066(10) 0.4723(4) 0.6893(3) 0.0261(17) Uani 1 1 d . . .
O5 O 0.6068(10) 0.1008(4) 0.6205(3) 0.0259(17) Uani 1 1 d . . .
O6 O 0.2791(10) 0.1034(4) 0.6770(3) 0.0259(17) Uani 1 1 d . . .
N1 N 0.293(3) 0.0617(11) 0.5054(8) 0.033(5) Uani 0.50 1 d PU A 1
N1A N 0.277(3) 0.1480(11) 0.5059(9) 0.033(5) Uani 0.50 1 d PU A 2
C1 C 0.7658(16) 0.2321(5) 0.6882(5) 0.023(2) Uani 1 1 d . . .
C2 C 0.8850(15) 0.2952(6) 0.6820(5) 0.024(3) Uani 1 1 d . . .
C3 C 0.8067(16) 0.3599(6) 0.6764(5) 0.024(3) Uani 1 1 d . . .
H3 H 0.6752 0.3640 0.6710 0.029 Uiso 1 1 calc R A .
C4 C 0.9159(16) 0.4196(6) 0.6785(5) 0.025(2) Uani 1 1 d . . .
H4 H 0.8605 0.4644 0.6755 0.031 Uiso 1 1 calc R . .
C5 C 1.1112(15) 0.4120(5) 0.6851(4) 0.019(2) Uani 1 1 d . . .
C6 C 1.1918(17) 0.3457(6) 0.6863(5) 0.025(3) Uani 1 1 d . . .
H6 H 1.3242 0.3409 0.6880 0.030 Uiso 1 1 calc R . .
C7 C 1.0807(16) 0.2877(5) 0.6850(4) 0.024(2) Uani 1 1 d . . .
H7 H 1.1355 0.2428 0.6861 0.029 Uiso 1 1 calc R A .
C8 C 1.2310(16) 0.4745(6) 0.6931(4) 0.023(3) Uani 1 1 d . . .
C9 C 0.453(4) 0.0876(13) 0.5935(11) 0.018(6) Uani 0.50 1 d PU A 1
C10 C 0.277(7) 0.0934(18) 0.623(2) 0.030(11) Uani 0.50 1 d PU A 1
C11 C 0.116(3) 0.0876(12) 0.5907(9) 0.019(5) Uani 0.50 1 d PU A 1
H11 H -0.0035 0.0941 0.6082 0.023 Uiso 0.50 1 calc PR A 1
C12 C 0.128(3) 0.0720(12) 0.5327(10) 0.023(5) Uani 0.50 1 d PU A 1
H12 H 0.0159 0.0685 0.5110 0.028 Uiso 0.50 1 calc PR A 1
C13 C 0.459(3) 0.0723(13) 0.5355(10) 0.025(5) Uani 0.50 1 d PU A 1
C14 C 0.291(4) 0.0475(14) 0.4434(10) 0.040(7) Uani 0.50 1 d PU A 1
H14A H 0.3619 0.0050 0.4354 0.060 Uiso 0.50 1 calc PR A 1
H14B H 0.3480 0.0866 0.4227 0.060 Uiso 0.50 1 calc PR A 1
H14C H 0.1611 0.0416 0.4305 0.060 Uiso 0.50 1 calc PR A 1
C15 C 0.641(3) 0.0579(14) 0.5040(10) 0.034(6) Uani 0.50 1 d PU A 1
H15A H 0.6195 0.0228 0.4742 0.051 Uiso 0.50 1 calc PR A 1
H15B H 0.7347 0.0408 0.5313 0.051 Uiso 0.50 1 calc PR A 1
H15C H 0.6863 0.1009 0.4861 0.051 Uiso 0.50 1 calc PR A 1
C9A C 0.445(4) 0.1205(14) 0.5898(12) 0.024(7) Uani 0.50 1 d PU A 2
C10A C 0.271(6) 0.1171(18) 0.6213(18) 0.022(8) Uani 0.50 1 d PU A 2
C11A C 0.108(3) 0.1348(13) 0.5910(10) 0.028(5) Uani 0.50 1 d PU A 2
H11A H -0.0094 0.1374 0.6104 0.033 Uiso 0.50 1 calc PR A 2
C12A C 0.118(4) 0.1479(14) 0.5344(11) 0.037(6) Uani 0.50 1 d PU A 2
H12A H 0.0060 0.1577 0.5140 0.044 Uiso 0.50 1 calc PR A 2
C13A C 0.444(3) 0.1358(12) 0.5332(10) 0.027(5) Uani 0.50 1 d PU A 2
C14A C 0.286(4) 0.1639(16) 0.4428(11) 0.050(8) Uani 0.50 1 d PU A 2
H14D H 0.3465 0.1253 0.4225 0.075 Uiso 0.50 1 calc PR A 2
H14E H 0.3576 0.2066 0.4367 0.075 Uiso 0.50 1 calc PR A 2
H14F H 0.1582 0.1701 0.4280 0.075 Uiso 0.50 1 calc PR A 2
C15A C 0.622(3) 0.1388(14) 0.4969(11) 0.036(6) Uani 0.50 1 d PU A 2
H15D H 0.6493 0.1873 0.4871 0.054 Uiso 0.50 1 calc PR A 2
H15E H 0.6031 0.1120 0.4616 0.054 Uiso 0.50 1 calc PR A 2
H15F H 0.7264 0.1192 0.5188 0.054 Uiso 0.50 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O5 2.172(7) . ?
Bi1 O6 2.332(7) . ?
Bi1 O2 2.341(8) . ?
Bi1 O3 2.355(7) 7_755 ?
Bi1 O4 2.578(7) 7_755 ?
Bi1 O1 2.620(7) . ?
Bi1 C8 2.844(11) 7_755 ?
Bi1 C1 2.867(11) . ?
O1 C1 1.270(14) . ?
O2 C1 1.300(13) . ?
O3 C8 1.299(13) . ?
O3 Bi1 2.355(7) 7_765 ?
O4 C8 1.257(14) . ?
O4 Bi1 2.578(7) 7_765 ?
O5 C9 1.29(3) . ?
O5 C9A 1.41(3) . ?
O6 C10 1.28(5) . ?
O6 C10A 1.32(4) . ?
N1 C12 1.35(3) . ?
N1 C13 1.39(3) . ?
N1 C14 1.47(3) . ?
N1A C12A 1.31(3) . ?
N1A C13A 1.37(3) . ?
N1A C14A 1.50(3) . ?
C1 C2 1.490(15) . ?
C2 C3 1.371(15) . ?
C2 C7 1.406(16) . ?
C3 C4 1.388(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(15) . ?
C5 C8 1.487(15) . ?
C6 C7 1.369(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 Bi1 2.844(11) 7_765 ?
C9 C13 1.38(3) . ?
C9 C10 1.43(6) . ?
C10 C11 1.37(5) . ?
C11 C12 1.38(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C15 1.52(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9A C13A 1.35(4) . ?
C9A C10A 1.44(6) . ?
C10A C11A 1.41(5) . ?
C11A C12A 1.34(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C15A 1.52(3) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

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
_geom_angle_publ_flag
O5 Bi1 O6 73.0(3) . . ?
O5 Bi1 O2 81.1(3) . . ?
O6 Bi1 O2 135.0(3) . . ?
O5 Bi1 O3 80.6(3) . 7_755 ?
O6 Bi1 O3 136.8(3) . 7_755 ?
O2 Bi1 O3 70.8(2) . 7_755 ?
O5 Bi1 O4 76.1(3) . 7_755 ?
O6 Bi1 O4 87.1(3) . 7_755 ?
O2 Bi1 O4 121.8(2) . 7_755 ?
O3 Bi1 O4 53.1(2) 7_755 7_755 ?
O5 Bi1 O1 75.7(3) . . ?
O6 Bi1 O1 85.0(3) . . ?
O2 Bi1 O1 52.8(2) . . ?
O3 Bi1 O1 121.1(2) 7_755 . ?
O4 Bi1 O1 151.8(2) 7_755 . ?
O5 Bi1 C8 77.3(3) . 7_755 ?
O6 Bi1 C8 112.1(3) . 7_755 ?
O2 Bi1 C8 96.8(3) . 7_755 ?
O3 Bi1 C8 26.9(3) 7_755 7_755 ?
O4 Bi1 C8 26.2(3) 7_755 7_755 ?
O1 Bi1 C8 141.8(3) . 7_755 ?
O5 Bi1 C1 77.0(3) . . ?
O6 Bi1 C1 110.1(3) . . ?
O2 Bi1 C1 26.5(3) . . ?
O3 Bi1 C1 96.1(3) 7_755 . ?
O4 Bi1 C1 141.9(3) 7_755 . ?
O1 Bi1 C1 26.3(3) . . ?
C8 Bi1 C1 120.4(3) 7_755 . ?
C1 O1 Bi1 87.7(6) . . ?
C1 O2 Bi1 99.9(7) . . ?
C8 O3 Bi1 98.0(6) . 7_765 ?
C8 O4 Bi1 88.8(7) . 7_765 ?
C9 O5 C9A 27.0(11) . . ?
C9 O5 Bi1 115.0(12) . . ?
C9A O5 Bi1 115.8(13) . . ?
C10 O6 C10A 20(2) . . ?
C10 O6 Bi1 112(2) . . ?
C10A O6 Bi1 113(2) . . ?
C12 N1 C13 118.8(18) . . ?
C12 N1 C14 119(2) . . ?
C13 N1 C14 122(2) . . ?
C12A N1A C13A 121(2) . . ?
C12A N1A C14A 122(2) . . ?
C13A N1A C14A 117(2) . . ?
O1 C1 O2 119.5(10) . . ?
O1 C1 C2 122.2(10) . . ?
O2 C1 C2 118.0(10) . . ?
O1 C1 Bi1 66.0(6) . . ?
O2 C1 Bi1 53.5(5) . . ?
C2 C1 Bi1 170.4(8) . . ?
C3 C2 C7 120.2(10) . . ?
C3 C2 C1 121.2(10) . . ?
C7 C2 C1 118.6(10) . . ?
C2 C3 C4 121.3(10) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.2(10) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.2(10) . . ?
C6 C5 C8 119.9(10) . . ?
C4 C5 C8 119.8(10) . . ?
C7 C6 C5 120.3(10) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 119.5(10) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O4 C8 O3 120.1(10) . . ?
O4 C8 C5 122.4(11) . . ?
O3 C8 C5 117.5(10) . . ?
O4 C8 Bi1 65.0(6) . 7_765 ?
O3 C8 Bi1 55.1(5) . 7_765 ?
C5 C8 Bi1 172.5(8) . 7_765 ?
O5 C9 C13 119(2) . . ?
O5 C9 C10 120(3) . . ?
C13 C9 C10 120(3) . . ?
O6 C10 C11 124(4) . . ?
O6 C10 C9 118(4) . . ?
C11 C10 C9 118(4) . . ?
C10 C11 C12 119(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N1 C12 C11 123(2) . . ?
N1 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N1 C13 C9 120(2) . . ?
N1 C13 C15 117.3(19) . . ?
C9 C13 C15 122(2) . . ?
C13A C9A O5 124(3) . . ?
C13A C9A C10A 120(3) . . ?
O5 C9A C10A 116(3) . . ?
O6 C10A C11A 125(4) . . ?
O6 C10A C9A 118(3) . . ?
C11A C10A C9A 117(3) . . ?
C12A C11A C10A 119(3) . . ?
C12A C11A H11A 120.4 . . ?
C10A C11A H11A 120.4 . . ?
N1A C12A C11A 123(2) . . ?
N1A C12A H12A 118.5 . . ?
C11A C12A H12A 118.5 . . ?
C9A C13A N1A 120(2) . . ?
C9A C13A C15A 123(2) . . ?
N1A C13A C15A 117(2) . . ?
N1A C14A H14D 109.5 . . ?
N1A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
N1A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C13A C15A H15D 109.5 . . ?
C13A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C13A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Bi1 O1 C1 -89.7(6) . . . . ?
O6 Bi1 O1 C1 -163.4(6) . . . . ?
O2 Bi1 O1 C1 -0.1(6) . . . . ?
O3 Bi1 O1 C1 -20.2(7) 7_755 . . . ?
O4 Bi1 O1 C1 -89.1(7) 7_755 . . . ?
C8 Bi1 O1 C1 -43.5(8) 7_755 . . . ?
O5 Bi1 O2 C1 78.9(6) . . . . ?
O6 Bi1 O2 C1 24.0(8) . . . . ?
O3 Bi1 O2 C1 162.0(7) 7_755 . . . ?
O4 Bi1 O2 C1 146.4(6) 7_755 . . . ?
O1 Bi1 O2 C1 0.1(6) . . . . ?
C8 Bi1 O2 C1 154.8(6) 7_755 . . . ?
O6 Bi1 O5 C9 -12.6(14) . . . . ?
O2 Bi1 O5 C9 -155.4(14) . . . . ?
O3 Bi1 O5 C9 132.8(14) 7_755 . . . ?
O4 Bi1 O5 C9 78.6(14) 7_755 . . . ?
O1 Bi1 O5 C9 -101.6(14) . . . . ?
C8 Bi1 O5 C9 105.6(14) 7_755 . . . ?
C1 Bi1 O5 C9 -128.7(14) . . . . ?
O6 Bi1 O5 C9A 17.4(14) . . . . ?
O2 Bi1 O5 C9A -125.4(14) . . . . ?
O3 Bi1 O5 C9A 162.7(14) 7_755 . . . ?
O4 Bi1 O5 C9A 108.6(14) 7_755 . . . ?
O1 Bi1 O5 C9A -71.7(14) . . . . ?
C8 Bi1 O5 C9A 135.5(14) 7_755 . . . ?
C1 Bi1 O5 C9A -98.7(14) . . . . ?
O5 Bi1 O6 C10 8.2(18) . . . . ?
O2 Bi1 O6 C10 65.9(18) . . . . ?
O3 Bi1 O6 C10 -46.7(19) 7_755 . . . ?
O4 Bi1 O6 C10 -68.1(18) 7_755 . . . ?
O1 Bi1 O6 C10 84.8(18) . . . . ?
C8 Bi1 O6 C10 -59.9(18) 7_755 . . . ?
C1 Bi1 O6 C10 77.0(18) . . . . ?
O5 Bi1 O6 C10A -13.6(18) . . . . ?
O2 Bi1 O6 C10A 44.0(18) . . . . ?
O3 Bi1 O6 C10A -68.6(18) 7_755 . . . ?
O4 Bi1 O6 C10A -90.0(18) 7_755 . . . ?
O1 Bi1 O6 C10A 62.9(18) . . . . ?
C8 Bi1 O6 C10A -81.7(18) 7_755 . . . ?
C1 Bi1 O6 C10A 55.2(18) . . . . ?
Bi1 O1 C1 O2 0.2(10) . . . . ?
Bi1 O1 C1 C2 -174.4(10) . . . . ?
Bi1 O2 C1 O1 -0.2(11) . . . . ?
Bi1 O2 C1 C2 174.6(8) . . . . ?
O5 Bi1 C1 O1 83.8(6) . . . . ?
O6 Bi1 C1 O1 17.6(7) . . . . ?
O2 Bi1 C1 O1 179.8(11) . . . . ?
O3 Bi1 C1 O1 162.7(6) 7_755 . . . ?
O4 Bi1 C1 O1 130.0(6) 7_755 . . . ?
C8 Bi1 C1 O1 150.4(6) 7_755 . . . ?
O5 Bi1 C1 O2 -96.0(6) . . . . ?
O6 Bi1 C1 O2 -162.2(6) . . . . ?
O3 Bi1 C1 O2 -17.1(7) 7_755 . . . ?
O4 Bi1 C1 O2 -49.8(8) 7_755 . . . ?
O1 Bi1 C1 O2 -179.8(11) . . . . ?
C8 Bi1 C1 O2 -29.4(7) 7_755 . . . ?
O5 Bi1 C1 C2 -126(5) . . . . ?
O6 Bi1 C1 C2 168(5) . . . . ?
O2 Bi1 C1 C2 -30(4) . . . . ?
O3 Bi1 C1 C2 -47(5) 7_755 . . . ?
O4 Bi1 C1 C2 -80(5) 7_755 . . . ?
O1 Bi1 C1 C2 150(5) . . . . ?
C8 Bi1 C1 C2 -59(5) 7_755 . . . ?
O1 C1 C2 C3 6.2(17) . . . . ?
O2 C1 C2 C3 -168.4(10) . . . . ?
Bi1 C1 C2 C3 -141(4) . . . . ?
O1 C1 C2 C7 -177.2(10) . . . . ?
O2 C1 C2 C7 8.2(15) . . . . ?
Bi1 C1 C2 C7 35(5) . . . . ?
C7 C2 C3 C4 -5.5(17) . . . . ?
C1 C2 C3 C4 171.1(10) . . . . ?
C2 C3 C4 C5 1.5(17) . . . . ?
C3 C4 C5 C6 3.4(16) . . . . ?
C3 C4 C5 C8 -174.2(9) . . . . ?
C4 C5 C6 C7 -4.4(17) . . . . ?
C8 C5 C6 C7 173.2(10) . . . . ?
C5 C6 C7 C2 0.5(17) . . . . ?
C3 C2 C7 C6 4.4(17) . . . . ?
C1 C2 C7 C6 -172.2(10) . . . . ?
Bi1 O4 C8 O3 1.3(9) 7_765 . . . ?
Bi1 O4 C8 C5 -178.5(9) 7_765 . . . ?
Bi1 O3 C8 O4 -1.4(10) 7_765 . . . ?
Bi1 O3 C8 C5 178.4(7) 7_765 . . . ?
C6 C5 C8 O4 14.9(15) . . . . ?
C4 C5 C8 O4 -167.5(10) . . . . ?
C6 C5 C8 O3 -164.8(10) . . . . ?
C4 C5 C8 O3 12.8(14) . . . . ?
C6 C5 C8 Bi1 -155(5) . . . 7_765 ?
C4 C5 C8 Bi1 23(6) . . . 7_765 ?
C9A O5 C9 C13 94(5) . . . . ?
Bi1 O5 C9 C13 -168.0(18) . . . . ?
C9A O5 C9 C10 -82(5) . . . . ?
Bi1 O5 C9 C10 16(3) . . . . ?
C10A O6 C10 C11 -85(12) . . . . ?
Bi1 O6 C10 C11 176(2) . . . . ?
C10A O6 C10 C9 95(12) . . . . ?
Bi1 O6 C10 C9 -3(3) . . . . ?
O5 C9 C10 O6 -8(4) . . . . ?
C13 C9 C10 O6 176(2) . . . . ?
O5 C9 C10 C11 172(2) . . . . ?
C13 C9 C10 C11 -4(4) . . . . ?
O6 C10 C11 C12 -176(3) . . . . ?
C9 C10 C11 C12 4(4) . . . . ?
C13 N1 C12 C11 -5(4) . . . . ?
C14 N1 C12 C11 -178(2) . . . . ?
C10 C11 C12 N1 0(4) . . . . ?
C12 N1 C13 C9 5(4) . . . . ?
C14 N1 C13 C9 178(2) . . . . ?
C12 N1 C13 C15 178(2) . . . . ?
C14 N1 C13 C15 -9(4) . . . . ?
O5 C9 C13 N1 -177(2) . . . . ?
C10 C9 C13 N1 -1(4) . . . . ?
O5 C9 C13 C15 11(4) . . . . ?
C10 C9 C13 C15 -173(3) . . . . ?
C9 O5 C9A C13A -99(5) . . . . ?
Bi1 O5 C9A C13A 166(2) . . . . ?
C9 O5 C9A C10A 75(5) . . . . ?
Bi1 O5 C9A C10A -20(3) . . . . ?
C10 O6 C10A C11A 104(12) . . . . ?
Bi1 O6 C10A C11A -166(3) . . . . ?
C10 O6 C10A C9A -82(11) . . . . ?
Bi1 O6 C10A C9A 8(3) . . . . ?
C13A C9A C10A O6 -179(2) . . . . ?
O5 C9A C10A O6 7(4) . . . . ?
C13A C9A C10A C11A -4(4) . . . . ?
O5 C9A C10A C11A -178(2) . . . . ?
O6 C10A C11A C12A 180(3) . . . . ?
C9A C10A C11A C12A 5(4) . . . . ?
C13A N1A C12A C11A -1(4) . . . . ?
C14A N1A C12A C11A -179(3) . . . . ?
C10A C11A C12A N1A -3(4) . . . . ?
O5 C9A C13A N1A 174(2) . . . . ?
C10A C9A C13A N1A 0(4) . . . . ?
O5 C9A C13A C15A -5(4) . . . . ?
C10A C9A C13A C15A -179(3) . . . . ?
C12A N1A C13A C9A 3(4) . . . . ?
C14A N1A C13A C9A -179(2) . . . . ?
C12A N1A C13A C15A -178(2) . . . . ?
C14A N1A C13A C15A -1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.876
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.223
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_h13mfm1
_database_code_depnum_ccdc_archive 'CCDC 1051715'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Bi N3 O8'
_chemical_formula_weight         658.44

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2050(4)
_cell_length_b                   10.6890(4)
_cell_length_c                   12.8740(3)
_cell_angle_alpha                67.243(2)
_cell_angle_beta                 86.289(2)
_cell_angle_gamma                61.884(2)
_cell_volume                     1130.18(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18773
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             642
_exptl_absorpt_coefficient_mu    7.853
# Absorption correction 

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_T_max  0.467
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17806
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         27.55
_reflns_number_total             5140
_reflns_number_gt                4448
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

Asymmetric unit comprises one bismuth centre, 2 deferiprones, half of a bdc
ligand, a water molecule and a DMF molecule. The hydrogens in the water
moiety were located adn refined at a distance of 0.98 Angstroms from O7, and
1.45 Angstroms from each other.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+1.4405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0053(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5140
_refine_ls_number_parameters     311
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Bi1 Bi 0.38659(2) 0.18162(2) 0.347119(16) 0.02563(10) Uani 1 1 d . . .
O1 O 0.6668(4) 0.1340(5) 0.3074(3) 0.0351(10) Uani 1 1 d . . .
O2 O 0.6002(4) 0.1153(5) 0.4777(3) 0.0337(9) Uani 1 1 d . . .
O3 O 0.2980(4) 0.2247(5) 0.5068(3) 0.0304(9) Uani 1 1 d . . .
O4 O 0.1333(4) 0.2986(5) 0.3171(3) 0.0312(9) Uani 1 1 d . . .
O5 O 0.3494(5) 0.2784(5) 0.1495(3) 0.0369(10) Uani 1 1 d . . .
O6 O 0.3617(5) 0.4127(5) 0.2867(3) 0.0334(9) Uani 1 1 d . . .
O7 O 0.5078(5) 0.1126(6) 0.7078(4) 0.0512(12) Uani 1 1 d D . .
O8 O 0.3505(5) 0.1836(6) 0.8888(4) 0.0474(12) Uani 1 1 d . . .
N1 N 0.3188(5) 0.7060(6) 0.0073(4) 0.0290(10) Uani 1 1 d . . .
N2 N -0.1552(5) 0.4032(6) 0.4933(4) 0.0292(10) Uani 1 1 d . . .
N3 N 0.1674(5) 0.2050(6) 1.0018(4) 0.0350(11) Uani 1 1 d . . .
C1 C 0.6971(6) 0.1041(7) 0.4096(5) 0.0288(12) Uani 1 1 d . . .
C2 C 0.8542(6) 0.0511(6) 0.4563(5) 0.0274(11) Uani 1 1 d . . .
C3 C 0.9691(6) 0.0171(6) 0.3899(5) 0.0271(11) Uani 1 1 d . . .
H3 H 0.9478 0.0277 0.3153 0.033 Uiso 1 1 calc R . .
C4 C 0.8852(6) 0.0324(6) 0.5670(5) 0.0270(11) Uani 1 1 d . . .
H4 H 0.8073 0.0534 0.6127 0.032 Uiso 1 1 calc R . .
C5 C 0.1538(6) 0.2786(6) 0.5060(5) 0.0271(11) Uani 1 1 d . . .
C6 C 0.0804(6) 0.3011(7) 0.5978(5) 0.0306(12) Uani 1 1 d . . .
H6 H 0.1368 0.2730 0.6666 0.037 Uiso 1 1 calc R . .
C7 C -0.0715(7) 0.3629(7) 0.5892(5) 0.0322(13) Uani 1 1 d . . .
H7 H -0.1197 0.3781 0.6523 0.039 Uiso 1 1 calc R . .
C8 C -0.0894(6) 0.3800(7) 0.4016(5) 0.0289(12) Uani 1 1 d . . .
C9 C 0.0654(6) 0.3199(6) 0.4056(5) 0.0271(11) Uani 1 1 d . . .
C10 C -0.3187(7) 0.4709(8) 0.4881(6) 0.0382(14) Uani 1 1 d . . .
H10A H -0.3484 0.3949 0.4907 0.057 Uiso 1 1 calc R . .
H10B H -0.3675 0.5637 0.4170 0.057 Uiso 1 1 calc R . .
H10C H -0.3495 0.4992 0.5530 0.057 Uiso 1 1 calc R . .
C11 C -0.1851(7) 0.4231(7) 0.2971(5) 0.0347(13) Uani 1 1 d . . .
H11A H -0.2503 0.3758 0.3184 0.052 Uiso 1 1 calc R . .
H11B H -0.1207 0.3856 0.2443 0.052 Uiso 1 1 calc R . .
H11C H -0.2469 0.5362 0.2603 0.052 Uiso 1 1 calc R . .
C12 C 0.3388(6) 0.4138(7) 0.1032(5) 0.0326(13) Uani 1 1 d . . .
C13 C 0.3185(6) 0.4978(7) -0.0171(5) 0.0320(12) Uani 1 1 d . . .
H13 H 0.3113 0.4534 -0.0663 0.038 Uiso 1 1 calc R . .
C14 C 0.3095(7) 0.6356(7) -0.0613(5) 0.0338(13) Uani 1 1 d . . .
H14 H 0.2964 0.6883 -0.1417 0.041 Uiso 1 1 calc R . .
C15 C 0.3397(7) 0.6292(7) 0.1237(5) 0.0341(13) Uani 1 1 d . . .
C16 C 0.3466(6) 0.4859(6) 0.1707(5) 0.0267(11) Uani 1 1 d . . .
C17 C 0.3100(8) 0.8579(7) -0.0485(6) 0.0430(16) Uani 1 1 d . . .
H17A H 0.2296 0.9315 -0.0228 0.064 Uiso 1 1 calc R . .
H17B H 0.2886 0.8946 -0.1312 0.064 Uiso 1 1 calc R . .
H17C H 0.4059 0.8497 -0.0292 0.064 Uiso 1 1 calc R . .
C18 C 0.3575(8) 0.7039(8) 0.1943(6) 0.0424(15) Uani 1 1 d . . .
H18A H 0.4302 0.7401 0.1659 0.064 Uiso 1 1 calc R . .
H18B H 0.3934 0.6285 0.2736 0.064 Uiso 1 1 calc R . .
H18C H 0.2604 0.7923 0.1898 0.064 Uiso 1 1 calc R . .
C19 C 0.3102(7) 0.1498(8) 0.9833(6) 0.0385(14) Uani 1 1 d . . .
H19 H 0.3861 0.0794 1.0476 0.046 Uiso 1 1 calc R . .
C20 C 0.1319(8) 0.1597(10) 1.1173(6) 0.0512(18) Uani 1 1 d . . .
H20A H 0.0916 0.2484 1.1384 0.077 Uiso 1 1 calc R . .
H20B H 0.2232 0.0744 1.1698 0.077 Uiso 1 1 calc R . .
H20C H 0.0571 0.1256 1.1214 0.077 Uiso 1 1 calc R . .
C21 C 0.0455(8) 0.3176(11) 0.9090(7) 0.063(2) Uani 1 1 d . . .
H21A H -0.0191 0.2746 0.9046 0.094 Uiso 1 1 calc R . .
H21B H 0.0865 0.3423 0.8374 0.094 Uiso 1 1 calc R . .
H21C H -0.0134 0.4122 0.9223 0.094 Uiso 1 1 calc R . .
H7A H 0.426(5) 0.188(7) 0.645(4) 0.076 Uiso 1 1 d D . .
H7B H 0.447(6) 0.131(9) 0.768(4) 0.076 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O6 2.172(4) . ?
Bi1 O4 2.259(4) . ?
Bi1 O3 2.314(4) . ?
Bi1 O5 2.325(4) . ?
Bi1 O2 2.486(4) . ?
Bi1 O1 2.709(4) . ?
O1 C1 1.251(7) . ?
O2 C1 1.272(7) . ?
O3 C5 1.303(6) . ?
O4 C9 1.334(7) . ?
O5 C12 1.286(7) . ?
O6 C16 1.371(7) . ?
O7 H7A 0.979(5) . ?
O7 H7B 0.980(5) . ?
O8 C19 1.230(8) . ?
N1 C15 1.374(7) . ?
N1 C14 1.395(8) . ?
N1 C17 1.459(7) . ?
N2 C7 1.349(8) . ?
N2 C8 1.368(8) . ?
N2 C10 1.467(7) . ?
N3 C19 1.335(8) . ?
N3 C21 1.446(9) . ?
N3 C20 1.454(8) . ?
C1 C2 1.502(8) . ?
C2 C3 1.395(8) . ?
C2 C4 1.396(8) . ?
C3 C4 1.392(8) 2_756 ?
C3 H3 0.9500 . ?
C4 C3 1.392(8) 2_756 ?
C4 H4 0.9500 . ?
C5 C6 1.397(8) . ?
C5 C9 1.419(8) . ?
C6 C7 1.361(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.392(8) . ?
C8 C11 1.498(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C16 1.393(8) . ?
C12 C13 1.428(8) . ?
C13 C14 1.317(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.380(8) . ?
C15 C18 1.489(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
_geom_angle_publ_flag
O6 Bi1 O4 86.74(15) . . ?
O6 Bi1 O3 84.30(14) . . ?
O4 Bi1 O3 71.85(13) . . ?
O6 Bi1 O5 74.09(15) . . ?
O4 Bi1 O5 80.97(14) . . ?
O3 Bi1 O5 146.10(15) . . ?
O6 Bi1 O2 82.62(15) . . ?
O4 Bi1 O2 142.24(14) . . ?
O3 Bi1 O2 71.10(13) . . ?
O5 Bi1 O2 129.53(14) . . ?
O6 Bi1 O1 76.90(14) . . ?
O4 Bi1 O1 158.20(14) . . ?
O3 Bi1 O1 119.84(12) . . ?
O5 Bi1 O1 80.74(13) . . ?
O2 Bi1 O1 50.27(12) . . ?
C1 O1 Bi1 88.4(3) . . ?
C1 O2 Bi1 98.3(3) . . ?
C5 O3 Bi1 114.9(3) . . ?
C9 O4 Bi1 115.4(3) . . ?
C12 O5 Bi1 111.9(4) . . ?
C16 O6 Bi1 114.4(3) . . ?
H7A O7 H7B 95.5(6) . . ?
C15 N1 C14 119.4(5) . . ?
C15 N1 C17 122.6(5) . . ?
C14 N1 C17 118.0(5) . . ?
C7 N2 C8 120.8(5) . . ?
C7 N2 C10 119.4(5) . . ?
C8 N2 C10 119.8(5) . . ?
C19 N3 C21 121.1(6) . . ?
C19 N3 C20 120.2(6) . . ?
C21 N3 C20 118.6(5) . . ?
O1 C1 O2 122.8(5) . . ?
O1 C1 C2 119.7(5) . . ?
O2 C1 C2 117.5(5) . . ?
C3 C2 C4 120.3(5) . . ?
C3 C2 C1 119.9(5) . . ?
C4 C2 C1 119.8(5) . . ?
C4 C3 C2 120.0(5) 2_756 . ?
C4 C3 H3 120.0 2_756 . ?
C2 C3 H3 120.0 . . ?
C3 C4 C2 119.7(5) 2_756 . ?
C3 C4 H4 120.2 2_756 . ?
C2 C4 H4 120.2 . . ?
O3 C5 C6 123.7(5) . . ?
O3 C5 C9 118.4(5) . . ?
C6 C5 C9 118.0(5) . . ?
C7 C6 C5 120.3(5) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 C6 121.6(5) . . ?
N2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N2 C8 C9 119.7(5) . . ?
N2 C8 C11 119.6(5) . . ?
C9 C8 C11 120.7(5) . . ?
O4 C9 C8 121.4(5) . . ?
O4 C9 C5 119.0(5) . . ?
C8 C9 C5 119.6(5) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 C16 120.3(5) . . ?
O5 C12 C13 123.1(5) . . ?
C16 C12 C13 116.6(5) . . ?
C14 C13 C12 121.3(6) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 N1 121.5(5) . . ?
C13 C14 H14 119.2 . . ?
N1 C14 H14 119.2 . . ?
N1 C15 C16 119.5(5) . . ?
N1 C15 C18 118.0(5) . . ?
C16 C15 C18 122.5(6) . . ?
O6 C16 C15 119.2(5) . . ?
O6 C16 C12 119.2(5) . . ?
C15 C16 C12 121.7(5) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O8 C19 N3 124.6(6) . . ?
O8 C19 H19 117.7 . . ?
N3 C19 H19 117.7 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Bi1 O1 C1 93.5(4) . . . . ?
O4 Bi1 O1 C1 135.8(4) . . . . ?
O3 Bi1 O1 C1 18.0(4) . . . . ?
O5 Bi1 O1 C1 169.1(4) . . . . ?
O2 Bi1 O1 C1 2.2(3) . . . . ?
O6 Bi1 O2 C1 -81.3(4) . . . . ?
O4 Bi1 O2 C1 -156.1(3) . . . . ?
O3 Bi1 O2 C1 -167.7(4) . . . . ?
O5 Bi1 O2 C1 -19.0(4) . . . . ?
O1 Bi1 O2 C1 -2.2(3) . . . . ?
O6 Bi1 O3 C5 94.6(4) . . . . ?
O4 Bi1 O3 C5 6.2(3) . . . . ?
O5 Bi1 O3 C5 44.6(5) . . . . ?
O2 Bi1 O3 C5 178.7(4) . . . . ?
O1 Bi1 O3 C5 166.0(3) . . . . ?
O6 Bi1 O4 C9 -90.4(4) . . . . ?
O3 Bi1 O4 C9 -5.3(4) . . . . ?
O5 Bi1 O4 C9 -164.8(4) . . . . ?
O2 Bi1 O4 C9 -16.8(5) . . . . ?
O1 Bi1 O4 C9 -131.5(4) . . . . ?
O6 Bi1 O5 C12 2.5(4) . . . . ?
O4 Bi1 O5 C12 91.7(4) . . . . ?
O3 Bi1 O5 C12 55.0(5) . . . . ?
O2 Bi1 O5 C12 -63.4(4) . . . . ?
O1 Bi1 O5 C12 -76.4(4) . . . . ?
O4 Bi1 O6 C16 -84.9(3) . . . . ?
O3 Bi1 O6 C16 -157.0(4) . . . . ?
O5 Bi1 O6 C16 -3.4(3) . . . . ?
O2 Bi1 O6 C16 131.4(4) . . . . ?
O1 Bi1 O6 C16 80.6(3) . . . . ?
Bi1 O1 C1 O2 -3.9(6) . . . . ?
Bi1 O1 C1 C2 175.4(5) . . . . ?
Bi1 O2 C1 O1 4.3(6) . . . . ?
Bi1 O2 C1 C2 -175.1(4) . . . . ?
O1 C1 C2 C3 -7.9(8) . . . . ?
O2 C1 C2 C3 171.5(5) . . . . ?
O1 C1 C2 C4 173.6(5) . . . . ?
O2 C1 C2 C4 -6.9(8) . . . . ?
C4 C2 C3 C4 -1.4(9) . . . 2_756 ?
C1 C2 C3 C4 -179.9(5) . . . 2_756 ?
C3 C2 C4 C3 1.4(9) . . . 2_756 ?
C1 C2 C4 C3 179.9(5) . . . 2_756 ?
Bi1 O3 C5 C6 175.0(4) . . . . ?
Bi1 O3 C5 C9 -6.4(6) . . . . ?
O3 C5 C6 C7 177.7(5) . . . . ?
C9 C5 C6 C7 -1.0(8) . . . . ?
C8 N2 C7 C6 1.4(9) . . . . ?
C10 N2 C7 C6 -179.4(5) . . . . ?
C5 C6 C7 N2 0.5(9) . . . . ?
C7 N2 C8 C9 -2.6(8) . . . . ?
C10 N2 C8 C9 178.2(5) . . . . ?
C7 N2 C8 C11 178.8(5) . . . . ?
C10 N2 C8 C11 -0.4(8) . . . . ?
Bi1 O4 C9 C8 -175.2(4) . . . . ?
Bi1 O4 C9 C5 4.2(6) . . . . ?
N2 C8 C9 O4 -178.6(5) . . . . ?
C11 C8 C9 O4 -0.1(8) . . . . ?
N2 C8 C9 C5 2.1(8) . . . . ?
C11 C8 C9 C5 -179.4(5) . . . . ?
O3 C5 C9 O4 1.6(8) . . . . ?
C6 C5 C9 O4 -179.6(5) . . . . ?
O3 C5 C9 C8 -179.0(5) . . . . ?
C6 C5 C9 C8 -0.3(8) . . . . ?
Bi1 O5 C12 C16 -1.3(7) . . . . ?
Bi1 O5 C12 C13 178.8(4) . . . . ?
O5 C12 C13 C14 -179.3(6) . . . . ?
C16 C12 C13 C14 0.8(9) . . . . ?
C12 C13 C14 N1 -0.3(9) . . . . ?
C15 N1 C14 C13 0.8(9) . . . . ?
C17 N1 C14 C13 179.1(6) . . . . ?
C14 N1 C15 C16 -1.9(8) . . . . ?
C17 N1 C15 C16 179.9(5) . . . . ?
C14 N1 C15 C18 176.7(5) . . . . ?
C17 N1 C15 C18 -1.5(8) . . . . ?
Bi1 O6 C16 C15 -175.9(4) . . . . ?
Bi1 O6 C16 C12 4.1(6) . . . . ?
N1 C15 C16 O6 -177.5(5) . . . . ?
C18 C15 C16 O6 3.9(9) . . . . ?
N1 C15 C16 C12 2.5(9) . . . . ?
C18 C15 C16 C12 -176.1(6) . . . . ?
O5 C12 C16 O6 -1.8(8) . . . . ?
C13 C12 C16 O6 178.1(5) . . . . ?
O5 C12 C16 C15 178.2(5) . . . . ?
C13 C12 C16 C15 -1.9(8) . . . . ?
C21 N3 C19 O8 -2.6(10) . . . . ?
C20 N3 C19 O8 -178.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         2.159
_refine_diff_density_min         -2.069
_refine_diff_density_rms         0.180
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_k13mfm5
_database_code_depnum_ccdc_archive 'CCDC 1051716'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Bi N3 O9'
_chemical_formula_weight         674.44

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3170(1)
_cell_length_b                   10.6650(1)
_cell_length_c                   12.7980(2)
_cell_angle_alpha                108.125(1)
_cell_angle_beta                 93.568(1)
_cell_angle_gamma                118.699(1)
_cell_volume                     1135.44(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18122
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             658
_exptl_absorpt_coefficient_mu    7.822
# Absorption correction 

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.179
_exptl_absorpt_correction_T_max  0.235
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22651
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5180
_reflns_number_gt                5000
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The asymmetric unit is composed of one bismuth centre, 2 
deferiprone based ligands, half of a dihydroxy-benzenedicarboxylate 
ligand, one guest water molecule and one DMF guest.
The hydrogens in the water were located and refined subject to being 
a distance of 0.98Å from O10. The hydroxyl group pertaining to the 
functionalised BDC ligand was seen to be disordered in a 70:30 ratio 
between locations O7A and O7B, respectively. 
There was some evidence for the fractional-occupancy hydrogen atom 
associated with O7A in the penultimate difference Fourier map. 
This was ultimately included at a calculated position. 
The corresponding 30% occupancy hydrogen attached to O7B 
could not be reliably located and hence was omitted. 
There is a high probability, however, that it occupies a 
position that would facilitate hydrogen bonding to O5. 
The fractional occupancy phenyl hydrogens attached to 
C3/C4 were also omitted from the refinement, due to the disorder. 
There is hydrogen bonding present in the asymmetric unit.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0309P)²+1.0596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5180
_refine_ls_number_parameters     335
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
Bi1 Bi 0.567342(11) 0.682363(12) 0.654581(8) 0.01784(6) Uani 1 1 d . . .
O1 O 0.5218(3) 0.7261(3) 0.49333(19) 0.0214(5) Uani 1 1 d . . .
O2 O 0.4288(3) 0.7938(3) 0.68387(19) 0.0214(5) Uani 1 1 d . . .
O3 O 0.6280(3) 0.7794(3) 0.8511(2) 0.0223(5) Uani 1 1 d . . .
O4 O 0.7721(3) 0.9141(3) 0.71188(19) 0.0222(5) Uani 1 1 d . . .
O5 O 0.7977(3) 0.6292(3) 0.6910(2) 0.0273(5) Uani 1 1 d . . .
O6 O 0.7223(3) 0.6229(3) 0.5223(2) 0.0260(5) Uani 1 1 d . . .
O7A O 0.8723(4) 0.5921(4) 0.3658(3) 0.0228(7) Uani 0.70 1 d PD . .
O7B O 0.9701(8) 0.5174(9) 0.7144(7) 0.0215(15) Uani 0.30 1 d P . .
O9 O 0.5433(3) 0.6891(3) 0.1134(3) 0.0365(6) Uani 1 1 d . . .
O10 O 0.6026(3) 0.6073(3) 0.2952(2) 0.0342(6) Uani 1 1 d D . .
N1 N 0.3794(3) 0.7122(3) 0.0048(3) 0.0249(6) Uani 1 1 d . . .
N2 N 1.0225(3) 1.2023(3) 0.9880(2) 0.0217(6) Uani 1 1 d . . .
N3 N 0.2489(3) 0.9057(3) 0.5103(2) 0.0206(5) Uani 1 1 d . . .
C1 C 0.8023(4) 0.6045(4) 0.5887(3) 0.0208(6) Uani 1 1 d . . .
C2 C 0.9055(3) 0.5516(4) 0.5423(3) 0.0191(6) Uani 1 1 d . . .
C3 C 0.9283(4) 0.5435(4) 0.4338(3) 0.0204(6) Uani 1 1 d . . .
C4 C 0.9773(4) 0.5080(4) 0.6071(3) 0.0192(6) Uani 1 1 d . . .
C5 C 0.8323(4) 0.9874(4) 0.8249(3) 0.0191(6) Uani 1 1 d . . .
C6 C 0.9675(4) 1.1290(4) 0.8717(3) 0.0214(6) Uani 1 1 d . . .
C7 C 0.9467(4) 1.1359(4) 1.0576(3) 0.0235(7) Uani 1 1 d . . .
H7 H 0.9870 1.1892 1.1376 0.028 Uiso 1 1 calc R . .
C8 C 0.8141(4) 0.9946(4) 1.0148(3) 0.0225(6) Uani 1 1 d . . .
H8 H 0.7633 0.9505 1.0650 0.027 Uiso 1 1 calc R . .
C9 C 0.7519(3) 0.9133(4) 0.8964(3) 0.0186(6) Uani 1 1 d . . .
C10 C 1.0584(4) 1.2054(4) 0.7996(3) 0.0316(8) Uani 1 1 d . . .
H10C H 1.0543 1.2978 0.8077 0.047 Uiso 1 1 calc R . .
H10D H 1.0156 1.1327 0.7198 0.047 Uiso 1 1 calc R . .
H10E H 1.1648 1.2357 0.8239 0.047 Uiso 1 1 calc R . .
C11 C 1.1669(4) 1.3533(4) 1.0403(3) 0.0295(8) Uani 1 1 d . . .
H11A H 1.1891 1.3870 1.1231 0.044 Uiso 1 1 calc R . .
H11B H 1.1582 1.4301 1.0189 0.044 Uiso 1 1 calc R . .
H11C H 1.2499 1.3434 1.0135 0.044 Uiso 1 1 calc R . .
C12 C 0.3828(3) 0.8180(4) 0.5965(3) 0.0191(6) Uani 1 1 d . . .
C13 C 0.2902(3) 0.8791(4) 0.6022(3) 0.0201(6) Uani 1 1 d . . .
C14 C 0.2925(4) 0.8696(4) 0.4145(3) 0.0225(7) Uani 1 1 d . . .
H14 H 0.2615 0.8889 0.3527 0.027 Uiso 1 1 calc R . .
C15 C 0.3815(4) 0.8050(4) 0.4040(3) 0.0215(6) Uani 1 1 d . . .
H15 H 0.4088 0.7774 0.3346 0.026 Uiso 1 1 calc R . .
C16 C 0.4315(3) 0.7801(4) 0.4946(3) 0.0190(6) Uani 1 1 d . . .
C17 C 0.2339(4) 0.9174(4) 0.7055(3) 0.0244(7) Uani 1 1 d . . .
H17A H 0.2523 0.8710 0.7555 0.037 Uiso 1 1 calc R . .
H17B H 0.1242 0.8758 0.6826 0.037 Uiso 1 1 calc R . .
H17C H 0.2885 1.0303 0.7461 0.037 Uiso 1 1 calc R . .
C18 C 0.1561(4) 0.9775(4) 0.5175(3) 0.0260(7) Uani 1 1 d . . .
H18A H 0.1550 1.0085 0.4531 0.039 Uiso 1 1 calc R . .
H18B H 0.2004 1.0691 0.5887 0.039 Uiso 1 1 calc R . .
H18C H 0.0514 0.9025 0.5154 0.039 Uiso 1 1 calc R . .
C19 C 0.4642(4) 0.6546(4) 0.0214(3) 0.0250(7) Uani 1 1 d . . .
H19 H 0.4637 0.5803 -0.0434 0.030 Uiso 1 1 calc R . .
C20 C 0.3774(6) 0.8301(6) 0.0984(4) 0.0450(11) Uani 1 1 d . . .
H20A H 0.4342 0.8451 0.1700 0.067 Uiso 1 1 calc R . .
H20B H 0.2715 0.7969 0.1012 0.067 Uiso 1 1 calc R . .
H20C H 0.4252 0.9280 0.0873 0.067 Uiso 1 1 calc R . .
C21 C 0.2953(5) 0.6678(5) -0.1086(3) 0.0379(9) Uani 1 1 d . . .
H21A H 0.3410 0.7566 -0.1311 0.057 Uiso 1 1 calc R . .
H21B H 0.1886 0.6347 -0.1091 0.057 Uiso 1 1 calc R . .
H21C H 0.2994 0.5820 -0.1623 0.057 Uiso 1 1 calc R . .
H10A H 0.582(6) 0.638(6) 0.234(3) 0.050(14) Uiso 1 1 d D . .
H10B H 0.583(9) 0.664(8) 0.363(4) 0.13(3) Uiso 1 1 d D . .
H7A H 0.798(6) 0.610(7) 0.401(5) 0.039(17) Uiso 0.70 1 d PD . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O4 2.185(2) . ?
Bi1 O2 2.239(2) . ?
Bi1 O3 2.313(2) . ?
Bi1 O1 2.321(2) . ?
Bi1 O6 2.543(2) . ?
Bi1 O5 2.739(2) . ?
O1 C16 1.308(4) . ?
O2 C12 1.331(4) . ?
O3 C9 1.284(4) . ?
O4 C5 1.345(4) . ?
O5 C1 1.260(4) . ?
O6 C1 1.271(4) . ?
O7A C3 1.366(4) . ?
O7A H7A 0.979(5) . ?
O7B C4 1.355(8) . ?
O9 C19 1.228(5) . ?
O10 H10A 0.978(5) . ?
O10 H10B 0.978(5) . ?
N1 C19 1.328(4) . ?
N1 C21 1.451(5) . ?
N1 C20 1.452(5) . ?
N2 C7 1.361(4) . ?
N2 C6 1.376(4) . ?
N2 C11 1.471(4) . ?
N3 C14 1.339(4) . ?
N3 C13 1.381(4) . ?
N3 C18 1.478(4) . ?
C1 C2 1.501(4) . ?
C2 C4 1.396(5) . ?
C2 C3 1.405(5) . ?
C3 C4 1.387(4) 2_766 ?
C4 C3 1.387(4) 2_766 ?
C5 C6 1.376(5) . ?
C5 C9 1.437(4) . ?
C6 C10 1.496(5) . ?
C7 C8 1.362(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(5) . ?
C8 H8 0.9500 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.386(4) . ?
C12 C16 1.437(4) . ?
C13 C17 1.496(5) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
_geom_angle_publ_flag
O4 Bi1 O2 88.37(9) . . ?
O4 Bi1 O3 73.90(8) . . ?
O2 Bi1 O3 81.22(8) . . ?
O4 Bi1 O1 84.29(8) . . ?
O2 Bi1 O1 72.35(8) . . ?
O3 Bi1 O1 146.08(8) . . ?
O4 Bi1 O6 80.55(9) . . ?
O2 Bi1 O6 142.33(8) . . ?
O3 Bi1 O6 128.50(8) . . ?
O1 Bi1 O6 70.79(8) . . ?
O4 Bi1 O5 77.28(8) . . ?
O2 Bi1 O5 159.86(8) . . ?
O3 Bi1 O5 81.26(8) . . ?
O1 Bi1 O5 119.33(7) . . ?
O6 Bi1 O5 49.49(7) . . ?
C16 O1 Bi1 114.51(19) . . ?
C12 O2 Bi1 116.05(19) . . ?
C9 O3 Bi1 112.66(19) . . ?
C5 O4 Bi1 115.50(19) . . ?
C1 O5 Bi1 89.46(19) . . ?
C1 O6 Bi1 98.4(2) . . ?
C3 O7A H7A 105(4) . . ?
H10A O10 H10B 107(6) . . ?
C19 N1 C21 120.9(3) . . ?
C19 N1 C20 120.9(3) . . ?
C21 N1 C20 118.0(3) . . ?
C7 N2 C6 121.1(3) . . ?
C7 N2 C11 118.3(3) . . ?
C6 N2 C11 120.6(3) . . ?
C14 N3 C13 121.6(3) . . ?
C14 N3 C18 118.7(3) . . ?
C13 N3 C18 119.6(3) . . ?
O5 C1 O6 122.4(3) . . ?
O5 C1 C2 119.7(3) . . ?
O6 C1 C2 118.0(3) . . ?
C4 C2 C3 120.0(3) . . ?
C4 C2 C1 119.4(3) . . ?
C3 C2 C1 120.6(3) . . ?
O7A C3 C4 115.5(3) . 2_766 ?
O7A C3 C2 125.3(3) . . ?
C4 C3 C2 119.1(3) 2_766 . ?
O7B C4 C3 113.5(4) . 2_766 ?
O7B C4 C2 125.5(4) . . ?
C3 C4 C2 120.9(3) 2_766 . ?
O4 C5 C6 121.4(3) . . ?
O4 C5 C9 118.1(3) . . ?
C6 C5 C9 120.5(3) . . ?
N2 C6 C5 119.5(3) . . ?
N2 C6 C10 118.6(3) . . ?
C5 C6 C10 121.9(3) . . ?
N2 C7 C8 121.3(3) . . ?
N2 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O3 C9 C8 123.2(3) . . ?
O3 C9 C5 119.6(3) . . ?
C8 C9 C5 117.2(3) . . ?
C6 C10 H10C 109.5 . . ?
C6 C10 H10D 109.5 . . ?
H10C C10 H10D 109.5 . . ?
C6 C10 H10E 109.5 . . ?
H10C C10 H10E 109.5 . . ?
H10D C10 H10E 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 121.5(3) . . ?
O2 C12 C16 118.8(3) . . ?
C13 C12 C16 119.7(3) . . ?
N3 C13 C12 119.2(3) . . ?
N3 C13 C17 119.1(3) . . ?
C12 C13 C17 121.7(3) . . ?
N3 C14 C15 121.2(3) . . ?
N3 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O1 C16 C15 124.0(3) . . ?
O1 C16 C12 118.0(3) . . ?
C15 C16 C12 118.1(3) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O9 C19 N1 125.6(3) . . ?
O9 C19 H19 117.2 . . ?
N1 C19 H19 117.2 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Bi1 O1 C16 -95.2(2) . . . . ?
O2 Bi1 O1 C16 -5.1(2) . . . . ?
O3 Bi1 O1 C16 -45.6(3) . . . . ?
O6 Bi1 O1 C16 -177.1(2) . . . . ?
O5 Bi1 O1 C16 -167.1(2) . . . . ?
O4 Bi1 O2 C12 88.9(2) . . . . ?
O3 Bi1 O2 C12 162.9(2) . . . . ?
O1 Bi1 O2 C12 4.4(2) . . . . ?
O6 Bi1 O2 C12 16.7(3) . . . . ?
O5 Bi1 O2 C12 133.1(3) . . . . ?
O4 Bi1 O3 C9 -3.32(19) . . . . ?
O2 Bi1 O3 C9 -94.2(2) . . . . ?
O1 Bi1 O3 C9 -55.4(3) . . . . ?
O6 Bi1 O3 C9 60.1(2) . . . . ?
O5 Bi1 O3 C9 75.9(2) . . . . ?
O2 Bi1 O4 C5 85.4(2) . . . . ?
O3 Bi1 O4 C5 4.1(2) . . . . ?
O1 Bi1 O4 C5 157.8(2) . . . . ?
O6 Bi1 O4 C5 -130.7(2) . . . . ?
O5 Bi1 O4 C5 -80.3(2) . . . . ?
O4 Bi1 O5 C1 -91.3(2) . . . . ?
O2 Bi1 O5 C1 -136.8(2) . . . . ?
O3 Bi1 O5 C1 -166.6(2) . . . . ?
O1 Bi1 O5 C1 -15.4(2) . . . . ?
O6 Bi1 O5 C1 -2.88(18) . . . . ?
O4 Bi1 O6 C1 84.2(2) . . . . ?
O2 Bi1 O6 C1 158.95(19) . . . . ?
O3 Bi1 O6 C1 23.6(2) . . . . ?
O1 Bi1 O6 C1 171.4(2) . . . . ?
O5 Bi1 O6 C1 2.89(18) . . . . ?
Bi1 O5 C1 O6 5.2(3) . . . . ?
Bi1 O5 C1 C2 -175.0(3) . . . . ?
Bi1 O6 C1 O5 -5.7(4) . . . . ?
Bi1 O6 C1 C2 174.5(2) . . . . ?
O5 C1 C2 C4 9.7(5) . . . . ?
O6 C1 C2 C4 -170.5(3) . . . . ?
O5 C1 C2 C3 -171.3(3) . . . . ?
O6 C1 C2 C3 8.5(5) . . . . ?
C4 C2 C3 O7A -175.6(3) . . . . ?
C1 C2 C3 O7A 5.5(5) . . . . ?
C4 C2 C3 C4 -0.1(5) . . . 2_766 ?
C1 C2 C3 C4 -179.1(3) . . . 2_766 ?
C3 C2 C4 O7B 176.8(5) . . . . ?
C1 C2 C4 O7B -4.2(6) . . . . ?
C3 C2 C4 C3 0.1(5) . . . 2_766 ?
C1 C2 C4 C3 179.1(3) . . . 2_766 ?
Bi1 O4 C5 C6 175.1(2) . . . . ?
Bi1 O4 C5 C9 -4.6(3) . . . . ?
C7 N2 C6 C5 1.1(5) . . . . ?
C11 N2 C6 C5 179.7(3) . . . . ?
C7 N2 C6 C10 -178.1(3) . . . . ?
C11 N2 C6 C10 0.5(5) . . . . ?
O4 C5 C6 N2 177.9(3) . . . . ?
C9 C5 C6 N2 -2.4(5) . . . . ?
O4 C5 C6 C10 -3.0(5) . . . . ?
C9 C5 C6 C10 176.7(3) . . . . ?
C6 N2 C7 C8 0.2(5) . . . . ?
C11 N2 C7 C8 -178.4(3) . . . . ?
N2 C7 C8 C9 -0.1(5) . . . . ?
Bi1 O3 C9 C8 -178.6(2) . . . . ?
Bi1 O3 C9 C5 2.2(3) . . . . ?
C7 C8 C9 O3 179.5(3) . . . . ?
C7 C8 C9 C5 -1.2(5) . . . . ?
O4 C5 C9 O3 1.5(4) . . . . ?
C6 C5 C9 O3 -178.2(3) . . . . ?
O4 C5 C9 C8 -177.8(3) . . . . ?
C6 C5 C9 C8 2.5(4) . . . . ?
Bi1 O2 C12 C13 176.8(2) . . . . ?
Bi1 O2 C12 C16 -3.5(4) . . . . ?
C14 N3 C13 C12 2.0(5) . . . . ?
C18 N3 C13 C12 -177.2(3) . . . . ?
C14 N3 C13 C17 -178.1(3) . . . . ?
C18 N3 C13 C17 2.7(4) . . . . ?
O2 C12 C13 N3 178.3(3) . . . . ?
C16 C12 C13 N3 -1.4(5) . . . . ?
O2 C12 C13 C17 -1.5(5) . . . . ?
C16 C12 C13 C17 178.7(3) . . . . ?
C13 N3 C14 C15 -0.4(5) . . . . ?
C18 N3 C14 C15 178.8(3) . . . . ?
N3 C14 C15 C16 -1.8(5) . . . . ?
Bi1 O1 C16 C15 -175.7(2) . . . . ?
Bi1 O1 C16 C12 5.2(4) . . . . ?
C14 C15 C16 O1 -176.7(3) . . . . ?
C14 C15 C16 C12 2.3(5) . . . . ?
O2 C12 C16 O1 -1.3(4) . . . . ?
C13 C12 C16 O1 178.4(3) . . . . ?
O2 C12 C16 C15 179.5(3) . . . . ?
C13 C12 C16 C15 -0.7(5) . . . . ?
C21 N1 C19 O9 177.3(4) . . . . ?
C20 N1 C19 O9 2.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.758
_refine_diff_density_min         -2.366
_refine_diff_density_rms         0.133
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_k13mfm6
_database_code_depnum_ccdc_archive 'CCDC 1051717'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27.50 Bi N3.50 O8'
_chemical_formula_weight         665.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2600(2)
_cell_length_b                   10.7560(2)
_cell_length_c                   12.9810(3)
_cell_angle_alpha                66.799(1)
_cell_angle_beta                 87.134(1)
_cell_angle_gamma                62.981(1)
_cell_volume                     1158.34(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    26767
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             650
_exptl_absorpt_coefficient_mu    7.664
# Absorption correction 

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.273
_exptl_absorpt_correction_T_max  0.485
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22640
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         27.53
_reflns_number_total             5283
_reflns_number_gt                4807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The 1/2 of a BDC-NH2 in the asymmetric unit is near an inversion centre. 
This serves to generate the remainder of this ligand. However, it also 
means that the NH2 functionality is disorder at 2 positions on the 
ring. Consequently, this group has half-occupancy.  Neither the 
hydrogens attached to the N1 nor the hydrogen atom attached to 
C4 for 50% of the time could not be reliably located and hence were 
omitted from the refinement. 

O7 represent a water atom, at full occupancy. The hydrogens could not 
be located with confidence in this case either and were also omitted. 
However, proximity to O3 and O8 suggest that there may be hydrogen 
bonding present to the water hydrogen atoms.

Residual electron density was located in two regions, namely, 
around the guest DMP and the DFP ligand. Careful analysis indicated 
that there might be some disorder (8-10%) present in these regions, 
but elaborate attempts to model same did not improve the refinement 
significantly. On balance, therefore, disorder modelling was not 
included in this structural model. 

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0601P)²+4.5079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5283
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Bi1 Bi 0.11550(3) -0.18816(3) 0.151883(18) 0.04202(13) Uani 1 1 d . A 4
O1 O -0.1604(6) -0.1424(7) 0.1877(4) 0.0544(13) Uani 1 1 d . . .
O2 O -0.0999(6) -0.1162(7) 0.0174(4) 0.0517(12) Uani 1 1 d . . .
O3 O 0.2027(5) -0.2239(6) -0.0084(4) 0.0447(11) Uani 1 1 d . . .
O4 O 0.3665(6) -0.3050(6) 0.1851(4) 0.0476(11) Uani 1 1 d . . .
O5 O 0.1493(7) -0.2805(6) 0.3491(4) 0.0585(14) Uani 1 1 d . A 4
O6 O 0.1380(7) -0.4147(6) 0.2107(5) 0.0594(14) Uani 1 1 d . A 4
O7 O 0.0024(8) -0.1067(10) -0.2084(6) 0.085(2) Uani 1 1 d . . .
O8 O 0.1532(10) -0.1736(10) -0.3866(9) 0.098(3) Uani 1 1 d . B 4
N1 N -0.2942(19) -0.069(2) -0.1418(14) 0.077(5) Uani 0.50 1 d P . .
N2 N 0.6507(7) -0.4014(7) 0.0146(5) 0.0443(13) Uani 1 1 d . A .
N3 N 0.1718(7) -0.7039(7) 0.4901(5) 0.0518(15) Uani 1 1 d . A 4
N4 N 0.3404(11) -0.2135(16) -0.4891(10) 0.102(3) Uani 1 1 d . B 4
C1 C -0.1949(8) -0.1062(8) 0.0854(6) 0.0446(15) Uani 1 1 d . A .
C2 C -0.3528(8) -0.0526(7) 0.0395(6) 0.0422(14) Uani 1 1 d . . .
C3 C -0.4612(8) -0.0191(8) 0.1075(6) 0.0431(15) Uani 1 1 d . . .
H3 H -0.4345 -0.0324 0.1815 0.052 Uiso 1 1 calc R . .
C4 C -0.3919(8) -0.0333(7) -0.0683(6) 0.0425(14) Uani 1 1 d . . .
C5 C 0.4184(8) -0.2987(8) -0.0939(6) 0.0452(15) Uani 1 1 d . . .
H5 H 0.3631 -0.2694 -0.1635 0.054 Uiso 1 1 calc R A .
C6 C 0.5701(9) -0.3610(9) -0.0827(7) 0.0495(16) Uani 1 1 d . A .
H6 H 0.6186 -0.3756 -0.1444 0.059 Uiso 1 1 calc R . .
C7 C 0.5863(8) -0.3819(8) 0.1054(6) 0.0424(15) Uani 1 1 d . . .
C8 C 0.4326(8) -0.3209(8) 0.0983(5) 0.0407(14) Uani 1 1 d . A .
C9 C 0.8153(9) -0.4714(9) 0.0210(8) 0.0558(19) Uani 1 1 d . . .
H9A H 0.8430 -0.4888 -0.0473 0.084 Uiso 1 1 calc R A .
H9B H 0.8622 -0.5696 0.0881 0.084 Uiso 1 1 calc R . .
H9C H 0.8487 -0.4018 0.0265 0.084 Uiso 1 1 calc R . .
C10 C 0.6804(9) -0.4261(9) 0.2098(6) 0.0502(17) Uani 1 1 d . A .
H10A H 0.7433 -0.5378 0.2448 0.075 Uiso 1 1 calc R . .
H10B H 0.6172 -0.3942 0.2633 0.075 Uiso 1 1 calc R . .
H10C H 0.7427 -0.3756 0.1903 0.075 Uiso 1 1 calc R . .
C11 C 0.1581(8) -0.4112(9) 0.3905(8) 0.0533(19) Uani 1 1 d . A 4
C12 C 0.1750(9) -0.4966(10) 0.5150(7) 0.0541(18) Uani 1 1 d . A 4
H12 H 0.1786 -0.4511 0.5637 0.065 Uiso 1 1 calc R A 4
C13 C 0.1851(9) -0.6351(9) 0.5595(6) 0.056(2) Uani 1 1 d . A 4
H13 H 0.2016 -0.6896 0.6397 0.068 Uiso 1 1 calc R A 4
C14 C 0.1547(9) -0.6280(9) 0.3757(7) 0.0489(16) Uani 1 1 d . A 4
C15 C 0.1526(7) -0.4874(7) 0.3307(6) 0.0398(14) Uani 1 1 d . A 4
C16 C 0.1818(12) -0.8558(10) 0.5514(9) 0.069(2) Uani 1 1 d . A 4
H16A H 0.0946 -0.8557 0.5236 0.104 Uiso 1 1 calc R A 4
H16B H 0.1858 -0.8805 0.6327 0.104 Uiso 1 1 calc R A 4
H16C H 0.2716 -0.9329 0.5388 0.104 Uiso 1 1 calc R A 4
C17 C 0.1369(11) -0.6965(12) 0.3025(9) 0.067(2) Uani 1 1 d . A 4
H17A H 0.2297 -0.7889 0.3129 0.100 Uiso 1 1 calc R A 4
H17B H 0.1120 -0.6222 0.2229 0.100 Uiso 1 1 calc R A 4
H17C H 0.0573 -0.7238 0.3229 0.100 Uiso 1 1 calc R A 4
C18 C 0.1946(14) -0.1572(16) -0.4790(12) 0.088(3) Uani 1 1 d . B 4
H18 H 0.1227 -0.1035 -0.5453 0.106 Uiso 1 1 calc R B 4
C19 C 0.4577(12) -0.2825(16) -0.3961(12) 0.099(4) Uani 1 1 d . B 4
H19A H 0.4171 -0.2974 -0.3248 0.149 Uiso 1 1 calc R B 4
H19B H 0.5018 -0.2149 -0.4081 0.149 Uiso 1 1 calc R B 4
H19C H 0.5338 -0.3820 -0.3923 0.149 Uiso 1 1 calc R B 4
C20 C 0.385(3) -0.161(3) -0.6088(15) 0.205(13) Uani 1 1 d . B 4
H20A H 0.4936 -0.2109 -0.6020 0.308 Uiso 1 1 calc R B 4
H20B H 0.3463 -0.0491 -0.6422 0.308 Uiso 1 1 calc R B 4
H20C H 0.3445 -0.1888 -0.6575 0.308 Uiso 1 1 calc R B 4
C25 C 0.3456(8) -0.2783(8) -0.0043(6) 0.0405(14) Uani 1 1 d . A .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O6 2.148(6) . ?
Bi1 O4 2.268(5) . ?
Bi1 O3 2.326(5) . ?
Bi1 O5 2.331(5) . ?
Bi1 O2 2.510(5) . ?
Bi1 O1 2.694(5) . ?
O1 C1 1.246(9) . ?
O2 C1 1.279(9) . ?
O3 C25 1.303(8) . ?
O4 C8 1.314(9) . ?
O5 C11 1.252(9) . ?
O6 C15 1.420(9) . ?
O8 C18 1.224(14) . ?
N1 C4 1.381(16) . ?
N2 C6 1.347(10) . ?
N2 C7 1.365(10) . ?
N2 C9 1.495(10) . ?
N3 C14 1.359(10) . ?
N3 C13 1.417(11) . ?
N3 C16 1.464(10) . ?
N4 C18 1.357(15) . ?
N4 C19 1.444(16) . ?
N4 C20 1.56(2) . ?
C1 C2 1.512(10) . ?
C2 C4 1.383(10) . ?
C2 C3 1.391(10) . ?
C3 C4 1.388(11) 2_455 ?
C3 H3 0.9500 . ?
C4 C3 1.388(11) 2_455 ?
C5 C6 1.375(11) . ?
C5 C25 1.387(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.397(10) . ?
C7 C10 1.483(10) . ?
C8 C25 1.431(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C15 1.351(10) . ?
C11 C12 1.483(12) . ?
C12 C13 1.324(12) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.379(10) . ?
C14 C17 1.473(11) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
_geom_angle_publ_flag
O6 Bi1 O4 86.3(2) . . ?
O6 Bi1 O3 85.2(2) . . ?
O4 Bi1 O3 71.81(17) . . ?
O6 Bi1 O5 75.5(2) . . ?
O4 Bi1 O5 81.5(2) . . ?
O3 Bi1 O5 147.9(2) . . ?
O6 Bi1 O2 83.6(2) . . ?
O4 Bi1 O2 142.68(18) . . ?
O3 Bi1 O2 71.62(17) . . ?
O5 Bi1 O2 129.67(19) . . ?
O6 Bi1 O1 77.2(2) . . ?
O4 Bi1 O1 158.05(17) . . ?
O3 Bi1 O1 120.21(17) . . ?
O5 Bi1 O1 80.52(19) . . ?
O2 Bi1 O1 50.10(16) . . ?
C1 O1 Bi1 89.9(4) . . ?
C1 O2 Bi1 97.7(4) . . ?
C25 O3 Bi1 114.4(4) . . ?
C8 O4 Bi1 115.6(4) . . ?
C11 O5 Bi1 108.6(5) . . ?
C15 O6 Bi1 112.7(4) . . ?
C6 N2 C7 121.9(6) . . ?
C6 N2 C9 117.7(7) . . ?
C7 N2 C9 120.5(6) . . ?
C14 N3 C13 118.8(6) . . ?
C14 N3 C16 126.0(8) . . ?
C13 N3 C16 115.2(7) . . ?
C18 N4 C19 123.7(11) . . ?
C18 N4 C20 119.3(14) . . ?
C19 N4 C20 114.4(14) . . ?
O1 C1 O2 122.1(7) . . ?
O1 C1 C2 119.7(6) . . ?
O2 C1 C2 118.1(6) . . ?
C4 C2 C3 119.6(7) . . ?
C4 C2 C1 121.9(7) . . ?
C3 C2 C1 118.5(6) . . ?
C4 C3 C2 120.7(6) 2_455 . ?
C4 C3 H3 119.7 2_455 . ?
C2 C3 H3 119.7 . . ?
N1 C4 C2 125.3(9) . . ?
N1 C4 C3 114.9(9) . 2_455 ?
C2 C4 C3 119.7(6) . 2_455 ?
C6 C5 C25 120.5(7) . . ?
C6 C5 H5 119.7 . . ?
C25 C5 H5 119.7 . . ?
N2 C6 C5 120.8(7) . . ?
N2 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N2 C7 C8 119.2(6) . . ?
N2 C7 C10 119.5(7) . . ?
C8 C7 C10 121.3(7) . . ?
O4 C8 C7 121.2(6) . . ?
O4 C8 C25 119.2(6) . . ?
C7 C8 C25 119.6(6) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 C15 125.6(9) . . ?
O5 C11 C12 120.7(7) . . ?
C15 C11 C12 113.7(7) . . ?
C13 C12 C11 121.1(7) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 N3 121.4(7) . . ?
C12 C13 H13 119.3 . . ?
N3 C13 H13 119.3 . . ?
N3 C14 C15 119.1(7) . . ?
N3 C14 C17 119.3(8) . . ?
C15 C14 C17 121.6(8) . . ?
C11 C15 C14 125.7(8) . . ?
C11 C15 O6 117.5(7) . . ?
C14 C15 O6 116.8(6) . . ?
O8 C18 N4 121.7(13) . . ?
O8 C18 H18 119.1 . . ?
N4 C18 H18 119.1 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C25 C5 123.5(6) . . ?
O3 C25 C8 118.5(6) . . ?
C5 C25 C8 118.0(6) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Bi1 O1 C1 -95.4(5) . . . . ?
O4 Bi1 O1 C1 -137.4(5) . . . . ?
O3 Bi1 O1 C1 -18.8(5) . . . . ?
O5 Bi1 O1 C1 -172.6(5) . . . . ?
O2 Bi1 O1 C1 -3.1(4) . . . . ?
O6 Bi1 O2 C1 81.6(4) . . . . ?
O4 Bi1 O2 C1 156.8(4) . . . . ?
O3 Bi1 O2 C1 168.7(5) . . . . ?
O5 Bi1 O2 C1 16.5(5) . . . . ?
O1 Bi1 O2 C1 3.0(4) . . . . ?
O6 Bi1 O3 C25 -93.3(5) . . . . ?
O4 Bi1 O3 C25 -5.6(4) . . . . ?
O5 Bi1 O3 C25 -40.6(6) . . . . ?
O2 Bi1 O3 C25 -178.1(5) . . . . ?
O1 Bi1 O3 C25 -165.4(4) . . . . ?
O6 Bi1 O4 C8 92.1(5) . . . . ?
O3 Bi1 O4 C8 5.9(4) . . . . ?
O5 Bi1 O4 C8 167.9(5) . . . . ?
O2 Bi1 O4 C8 17.7(6) . . . . ?
O1 Bi1 O4 C8 132.9(5) . . . . ?
O6 Bi1 O5 C11 -2.4(5) . . . . ?
O4 Bi1 O5 C11 -90.7(5) . . . . ?
O3 Bi1 O5 C11 -57.3(7) . . . . ?
O2 Bi1 O5 C11 66.2(6) . . . . ?
O1 Bi1 O5 C11 76.7(5) . . . . ?
O4 Bi1 O6 C15 85.0(4) . . . . ?
O3 Bi1 O6 C15 157.0(5) . . . . ?
O5 Bi1 O6 C15 2.9(4) . . . . ?
O2 Bi1 O6 C15 -131.0(5) . . . . ?
O1 Bi1 O6 C15 -80.5(4) . . . . ?
Bi1 O1 C1 O2 5.5(7) . . . . ?
Bi1 O1 C1 C2 -176.2(6) . . . . ?
Bi1 O2 C1 O1 -5.9(8) . . . . ?
Bi1 O2 C1 C2 175.7(5) . . . . ?
O1 C1 C2 C4 -170.1(6) . . . . ?
O2 C1 C2 C4 8.3(10) . . . . ?
O1 C1 C2 C3 11.1(10) . . . . ?
O2 C1 C2 C3 -170.5(6) . . . . ?
C4 C2 C3 C4 0.0(11) . . . 2_455 ?
C1 C2 C3 C4 178.7(6) . . . 2_455 ?
C3 C2 C4 N1 -176.6(12) . . . . ?
C1 C2 C4 N1 4.7(15) . . . . ?
C3 C2 C4 C3 0.0(11) . . . 2_455 ?
C1 C2 C4 C3 -178.7(6) . . . 2_455 ?
C7 N2 C6 C5 -0.3(11) . . . . ?
C9 N2 C6 C5 178.7(7) . . . . ?
C25 C5 C6 N2 -0.9(11) . . . . ?
C6 N2 C7 C8 1.2(10) . . . . ?
C9 N2 C7 C8 -177.8(6) . . . . ?
C6 N2 C7 C10 -179.0(6) . . . . ?
C9 N2 C7 C10 2.0(9) . . . . ?
Bi1 O4 C8 C7 175.8(5) . . . . ?
Bi1 O4 C8 C25 -5.7(8) . . . . ?
N2 C7 C8 O4 177.7(6) . . . . ?
C10 C7 C8 O4 -2.1(10) . . . . ?
N2 C7 C8 C25 -0.8(9) . . . . ?
C10 C7 C8 C25 179.4(6) . . . . ?
Bi1 O5 C11 C15 1.5(9) . . . . ?
Bi1 O5 C11 C12 -178.0(6) . . . . ?
O5 C11 C12 C13 -179.7(8) . . . . ?
C15 C11 C12 C13 0.8(11) . . . . ?
C11 C12 C13 N3 -3.6(13) . . . . ?
C14 N3 C13 C12 2.9(12) . . . . ?
C16 N3 C13 C12 -178.6(8) . . . . ?
C13 N3 C14 C15 0.7(11) . . . . ?
C16 N3 C14 C15 -177.6(8) . . . . ?
C13 N3 C14 C17 -178.5(7) . . . . ?
C16 N3 C14 C17 3.2(12) . . . . ?
O5 C11 C15 C14 -176.5(7) . . . . ?
C12 C11 C15 C14 3.0(11) . . . . ?
O5 C11 C15 O6 1.1(11) . . . . ?
C12 C11 C15 O6 -179.4(6) . . . . ?
N3 C14 C15 C11 -3.8(12) . . . . ?
C17 C14 C15 C11 175.3(7) . . . . ?
N3 C14 C15 O6 178.5(6) . . . . ?
C17 C14 C15 O6 -2.3(11) . . . . ?
Bi1 O6 C15 C11 -3.3(8) . . . . ?
Bi1 O6 C15 C14 174.5(5) . . . . ?
C19 N4 C18 O8 -7(2) . . . . ?
C20 N4 C18 O8 -167.3(15) . . . . ?
Bi1 O3 C25 C5 -175.8(5) . . . . ?
Bi1 O3 C25 C8 4.9(7) . . . . ?
C6 C5 C25 O3 -178.1(7) . . . . ?
C6 C5 C25 C8 1.2(10) . . . . ?
O4 C8 C25 O3 0.4(9) . . . . ?
C7 C8 C25 O3 179.0(6) . . . . ?
O4 C8 C25 C5 -178.9(6) . . . . ?
C7 C8 C25 C5 -0.4(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         2.357
_refine_diff_density_min         -1.468
_refine_diff_density_rms         0.162

#===end
