# 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_Bi-BTC
_database_code_depnum_ccdc_archive 'CCDC 1404669'
_audit_update_record             
;
2015-08-11 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Bi-BTC
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Bi N O7, C3 H7 N O, 2(C H4 O )'
_chemical_formula_sum            'C17 H25 Bi N O10'
_chemical_formula_weight         626.19

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   10.137(2)
_cell_length_b                   15.017(3)
_cell_length_c                   11.422(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.441(2)
_cell_angle_gamma                90
_cell_volume                     1715.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7449
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.29

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.425
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    10.306
_shelx_estimated_absorpt_T_min   0.320
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_process_details   'Apex II Suite software'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19035
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             19035
_reflns_number_gt                15529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1070P)²+22.7131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         19035
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.871
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.60874(4) 0.94735(2) 0.39896(4) 0.02036(18) Uani 1 1 d . . . . .
C5 C 0.5646(11) 0.7441(8) 0.6642(10) 0.026(2) Uani 1 1 d . . . . .
O3 O 0.4546(8) 0.8687(5) 0.5645(8) 0.034(2) Uani 1 1 d . . . . .
O5 O 0.8561(9) 0.9490(6) 0.4151(10) 0.046(3) Uani 1 1 d . . . . .
O6 O 0.7278(7) 0.8603(5) 0.2929(7) 0.0276(18) Uani 1 1 d . . . . .
O7 O 0.5916(13) 1.0220(8) 0.2066(10) 0.056(3) Uani 1 1 d . . . . .
O4 O 0.6480(8) 0.8250(6) 0.5156(8) 0.035(2) Uani 1 1 d . . . . .
C8 C 0.5526(12) 0.8174(8) 0.5757(11) 0.029(3) Uani 1 1 d . . . . .
C6 C 0.6878(11) 0.7023(8) 0.7029(11) 0.029(3) Uani 1 1 d . . . . .
H018 H 0.7636 0.7219 0.6744 0.034 Uiso 1 1 calc R U . . .
C1 C 0.6985(10) 0.6327(8) 0.7826(10) 0.025(2) Uani 1 1 d . . . . .
C4 C 0.4509(11) 0.7143(8) 0.7082(11) 0.029(3) Uani 1 1 d . . . . .
H2 H 0.3683 0.7411 0.6834 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5875(11) 0.6038(8) 0.8265(10) 0.026(2) Uani 1 1 d . . . . .
H4 H 0.5952 0.5572 0.8810 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4632(11) 0.6440(8) 0.7898(11) 0.027(3) Uani 1 1 d . . . . .
C7 C 0.8303(11) 0.5895(8) 0.8210(10) 0.024(2) Uani 1 1 d . . . . .
O2 O 0.8369(8) 0.5157(6) 0.8719(7) 0.0278(18) Uani 1 1 d . . . . .
O1 O 0.9354(8) 0.6315(6) 0.7985(8) 0.033(2) Uani 1 1 d . . . . .
C9 C 0.8436(11) 0.8916(8) 0.3354(11) 0.028(3) Uani 1 1 d . . . . .
C10 C 0.496(3) 1.0609(12) 0.1571(18) 0.074(6) Uani 1 1 d . . . . .
H10 H 0.4169 1.0502 0.1859 0.089 Uiso 1 1 calc R U . . .
N1 N 0.4866(19) 1.1173(11) 0.0670(13) 0.089(6) Uani 1 1 d D . . . .
C11 C 0.364(3) 1.1586(17) 0.011(2) 0.140(13) Uani 1 1 d D . . . .
H11A H 0.3474 1.2108 0.0552 0.209 Uiso 1 1 calc R U . . .
H11B H 0.2913 1.1175 0.0102 0.209 Uiso 1 1 calc R U . . .
H11C H 0.3714 1.1751 -0.0685 0.209 Uiso 1 1 calc R U . . .
C12 C 0.603(3) 1.138(2) 0.016(3) 0.166(16) Uani 1 1 d D . . . .
H12A H 0.5766 1.1554 -0.0659 0.250 Uiso 1 1 calc R U . . .
H12B H 0.6602 1.0868 0.0194 0.250 Uiso 1 1 calc R U . . .
H12C H 0.6511 1.1863 0.0587 0.250 Uiso 1 1 calc R U . . .


_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 2.261(7) . ?
Bi1 O4 2.266(8) . ?
Bi1 O1 2.268(8) 4_575 ?
Bi1 O5 2.484(9) . ?
C5 C6 1.403(16) . ?
C5 C4 1.404(15) . ?
C5 C8 1.486(16) . ?
O3 C8 1.246(14) . ?
O5 C9 1.246(15) . ?
O6 C9 1.284(13) . ?
O7 C10 1.19(3) . ?
O4 C8 1.280(14) . ?
C6 C1 1.379(16) . ?
C1 C2 1.375(15) . ?
C1 C7 1.486(15) . ?
C4 C3 1.401(16) . ?
C2 C3 1.399(15) . ?
C3 C9 1.493(15) 4_576 ?
C7 O2 1.249(14) . ?
C7 O1 1.299(13) . ?
O1 Bi1 2.268(8) 4_676 ?
C9 C3 1.493(15) 4_675 ?
C10 N1 1.33(2) . ?
N1 C12 1.44(2) . ?
N1 C11 1.44(2) . ?

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 77.8(3) . . ?
O6 Bi1 O1 82.2(3) . 4_575 ?
O4 Bi1 O1 85.5(3) . 4_575 ?
O6 Bi1 O5 54.9(3) . . ?
O4 Bi1 O5 83.5(3) . . ?
O1 Bi1 O5 137.0(3) 4_575 . ?
C6 C5 C4 119.0(11) . . ?
C6 C5 C8 121.0(10) . . ?
C4 C5 C8 119.9(10) . . ?
C9 O5 Bi1 87.6(7) . . ?
C9 O6 Bi1 97.0(7) . . ?
C8 O4 Bi1 108.2(7) . . ?
O3 C8 O4 123.3(11) . . ?
O3 C8 C5 120.2(11) . . ?
O4 C8 C5 116.5(10) . . ?
C1 C6 C5 121.1(10) . . ?
C2 C1 C6 120.0(10) . . ?
C2 C1 C7 120.3(10) . . ?
C6 C1 C7 119.7(10) . . ?
C3 C4 C5 119.3(11) . . ?
C1 C2 C3 120.3(10) . . ?
C2 C3 C4 120.2(10) . . ?
C2 C3 C9 118.9(10) . 4_576 ?
C4 C3 C9 120.9(10) . 4_576 ?
O2 C7 O1 122.7(10) . . ?
O2 C7 C1 120.1(10) . . ?
O1 C7 C1 117.2(10) . . ?
C7 O1 Bi1 103.8(7) . 4_676 ?
O5 C9 O6 120.4(10) . . ?
O5 C9 C3 120.8(10) . 4_675 ?
O6 C9 C3 118.8(10) . 4_675 ?
O7 C10 N1 129(2) . . ?
C10 N1 C12 120(2) . . ?
C10 N1 C11 124(2) . . ?
C12 N1 C11 116(2) . . ?

_refine_diff_density_max         3.295
_refine_diff_density_min         -3.207
_refine_diff_density_rms         0.301

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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
_platon_squeeze_void_content
1 0.000 0.000 0.500 241 143 ' '
2 0.500 0.500 0.000 241 144 ' '
_platon_squeeze_details          ?
