# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_InIDA1
_database_code_depnum_ccdc_archive 'CCDC 1561408'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2016-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H5 Cl In N O4'
_chemical_formula_sum            'C4 H5 Cl In N O4'
_chemical_formula_weight         281.36
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.7276 1.3100 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   13.5719(4)
_cell_length_b                   8.7940(3)
_cell_length_c                   6.0584(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     723.08(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2792
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0494 before and 0.0278 after correction.
The Ratio of minimum to maximum transmission is 0.9172.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3412
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                856
_reflns_number_total             878
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0140
_refine_ls_R_factor_gt           0.0136
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+0.0812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0358
_refine_ls_wR_factor_ref         0.0360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Others
 Fixed Sof: In1(0.25) Cl1(0.25) O1(0.5) N1(0.25) H1(0.25) O2(0.5) C1(0.5)
 C2(0.5) H2A(0.5) H2B(0.5)
3.a Ternary CH refined with riding coordinates:
 N1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.035
;
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
In1 In 0.81750(2) 0.2500 0.39217(3) 0.01443(7) Uani 0.5 2 d S T P . .
Cl1 Cl 0.97290(4) 0.2500 0.58275(11) 0.02681(15) Uani 0.5 2 d S T P . .
O1 O 0.75881(9) 0.43298(18) 0.5969(2) 0.0274(3) Uani 0.5 1 d . . . . .
N1 N 0.65177(14) 0.2500 0.3131(3) 0.0145(4) Uani 0.5 2 d S T P . .
H1 H 0.6436 0.2500 0.1523 0.017 Uiso 0.5 2 calc RS T P . .
O2 O 0.63318(9) 0.58982(16) 0.6481(2) 0.0272(3) Uani 0.5 1 d . . . . .
C1 C 0.67204(11) 0.4757(2) 0.5605(3) 0.0187(3) Uani 0.5 1 d . . . . .
C2 C 0.60672(12) 0.3905(2) 0.4026(3) 0.0179(4) Uani 0.5 1 d . . . . .
H2A H 0.5460 0.3639 0.4777 0.022 Uiso 0.5 1 calc R . . . .
H2B H 0.5899 0.4571 0.2806 0.022 Uiso 0.5 1 calc R . . . .


_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
In1 Cl1 2.4044(6) . ?
In1 O1 2.1820(13) . ?
In1 O1 2.1820(13) 8_565 ?
In1 N1 2.2998(19) . ?
In1 O2 2.1491(13) 7_755 ?
In1 O2 2.1491(13) 2_664 ?
O1 C1 1.256(2) . ?
N1 H1 0.9800 . ?
N1 C2 1.481(2) . ?
N1 C2 1.481(2) 8_565 ?
O2 In1 2.1491(13) 2_665 ?
O2 C1 1.252(2) . ?
C1 C2 1.504(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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
O1 In1 Cl1 92.71(3) . . ?
O1 In1 Cl1 92.71(3) 8_565 . ?
O1 In1 O1 95.03(8) . 8_565 ?
O1 In1 N1 76.20(5) 8_565 . ?
O1 In1 N1 76.20(5) . . ?
N1 In1 Cl1 163.33(5) . . ?
O2 In1 Cl1 93.28(4) 2_664 . ?
O2 In1 Cl1 93.28(4) 7_755 . ?
O2 In1 O1 171.13(5) 2_664 8_565 ?
O2 In1 O1 171.13(5) 7_755 . ?
O2 In1 O1 91.22(6) 7_755 8_565 ?
O2 In1 O1 91.22(6) 2_664 . ?
O2 In1 N1 99.28(5) 7_755 . ?
O2 In1 N1 99.28(5) 2_664 . ?
O2 In1 O2 81.91(8) 7_755 2_664 ?
C1 O1 In1 117.59(12) . . ?
In1 N1 H1 108.5 . . ?
C2 N1 In1 109.12(10) 8_565 . ?
C2 N1 In1 109.12(10) . . ?
C2 N1 H1 108.5 . . ?
C2 N1 H1 108.5 8_565 . ?
C2 N1 C2 113.02(18) 8_565 . ?
C1 O2 In1 133.32(12) . 2_665 ?
O1 C1 C2 121.04(17) . . ?
O2 C1 O1 124.08(17) . . ?
O2 C1 C2 114.89(15) . . ?
N1 C2 C1 113.89(14) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?

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
In1 O1 C1 O2 -171.73(15) . . . . ?
In1 O1 C1 C2 7.8(2) . . . . ?
In1 N1 C2 C1 -13.06(18) . . . . ?
In1 O2 C1 O1 -3.6(3) 2_665 . . . ?
In1 O2 C1 C2 176.78(12) 2_665 . . . ?
O1 C1 C2 N1 4.5(3) . . . . ?
O2 C1 C2 N1 -175.94(16) . . . . ?
C2 N1 C2 C1 108.54(17) 8_565 . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Hydrothermal
####################################################################### 
# 
# 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_bi12
_database_code_depnum_ccdc_archive 'CCDC 1561409'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Bi N4 O8'
_chemical_formula_sum            'C18 H16 Bi N4 O8'
_chemical_formula_weight         625.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3852(6)
_cell_length_b                   9.6474(7)
_cell_length_c                   13.4442(9)
_cell_angle_alpha                72.378(6)
_cell_angle_beta                 74.943(6)
_cell_angle_gamma                62.844(7)
_cell_volume                     1021.60(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1430
_cell_measurement_theta_min      2.6070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.330
_diffrn_reflns_theta_min         1.606
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 110.00   1.00   40.00    --   27.63  54.00   0.00  180
  2  ω    -70.00 110.00   1.00   40.00    --   27.63  54.00 120.00  180
  3  ω    -70.00 110.00   1.00   40.00    --   27.63  54.00 240.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0592094000
_diffrn_orient_matrix_UB_12      0.0599541000
_diffrn_orient_matrix_UB_13      -0.0314867000
_diffrn_orient_matrix_UB_21      -0.0621231000
_diffrn_orient_matrix_UB_22      -0.0101855000
_diffrn_orient_matrix_UB_23      0.0407122000
_diffrn_orient_matrix_UB_31      -0.0010734000
_diffrn_orient_matrix_UB_32      0.0588083000
_diffrn_orient_matrix_UB_33      0.0219037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5849
_reflns_number_total             7803
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.459
_refine_diff_density_min         -1.703
_refine_diff_density_rms         0.213
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         7803
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C16, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C17)
Uanis(C17) = Uanis(C18)
4. Others
 Fixed Sof: O7A(0.5) O7B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C7(H7), C6(H6), C8(H8), C15(H15), C12(H12), C14(H14),
 C13(H13), C16(H16)
5.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.06844(2) 0.54850(2) 0.25022(2) 0.02546(6) Uani 1 1 d . . . . .
O1 O 0.1770(4) 0.3712(4) 0.6375(3) 0.0336(8) Uani 1 1 d . . . . .
O3 O 0.1613(4) 0.5115(5) 0.4048(3) 0.0381(9) Uani 1 1 d . . . . .
C3 C 0.4025(5) 0.5022(5) 0.4373(4) 0.0254(9) Uani 1 1 d . . . . .
C2 C 0.3466(5) 0.5030(5) 0.5435(4) 0.0254(9) Uani 1 1 d . . . . .
O4 O 0.3471(5) 0.5224(5) 0.2706(3) 0.0461(10) Uani 1 1 d . . . . .
C4 C 0.5545(5) 0.4998(6) 0.3948(4) 0.0264(9) Uani 1 1 d . . . . .
H4 H 0.590871 0.499997 0.323509 0.032 Uiso 1 1 calc R . . . .
C1 C 0.1840(5) 0.5053(6) 0.5986(4) 0.0267(9) Uani 1 1 d . . . . .
O2 O 0.0719(4) 0.6324(5) 0.6129(3) 0.0409(9) Uani 1 1 d . . . . .
C5 C 0.2994(6) 0.5115(6) 0.3650(4) 0.0301(10) Uani 1 1 d . . . . .
N2 N 0.0363(6) 0.8139(5) 0.2422(4) 0.0398(10) Uani 1 1 d . . . . .
N1 N 0.1939(5) 0.6697(6) 0.0788(3) 0.0366(10) Uani 1 1 d . . . . .
C11 C 0.0951(7) 0.8962(7) 0.1544(5) 0.0422(13) Uani 1 1 d . . . . .
C9 C 0.2661(11) 0.8768(10) -0.0248(6) 0.076(2) Uani 1 1 d . . . . .
H9 H 0.263434 0.977537 -0.034360 0.091 Uiso 1 1 calc R . . . .
C10 C 0.1865(7) 0.8145(7) 0.0675(5) 0.0461(14) Uani 1 1 d . . . . .
C7 C 0.3553(9) 0.6494(12) -0.0886(6) 0.072(2) Uani 1 1 d . . . . .
H7 H 0.413642 0.589967 -0.140093 0.086 Uiso 1 1 calc R . . . .
C6 C 0.2749(8) 0.5879(8) 0.0030(5) 0.0502(15) Uani 1 1 d . . . . .
H6 H 0.277509 0.487400 0.011782 0.060 Uiso 1 1 calc R . . . .
C8 C 0.3479(12) 0.7910(14) -0.1012(6) 0.092(3) Uani 1 1 d . . . . .
H8 H 0.399067 0.834494 -0.163115 0.111 Uiso 1 1 calc R . . . .
C15 C -0.0400(8) 0.8803(9) 0.3240(6) 0.0610(18) Uani 1 1 d . . . . .
H15 H -0.078317 0.821822 0.384497 0.073 Uiso 1 1 calc R . . . .
C12 C 0.0688(10) 1.0499(8) 0.1511(7) 0.071(2) Uani 1 1 d . . . . .
H12 H 0.106151 1.108328 0.090112 0.085 Uiso 1 1 calc R . . . .
C14 C -0.0655(11) 1.0329(10) 0.3240(8) 0.085(3) Uani 1 1 d . . . . .
H14 H -0.118986 1.076542 0.383208 0.102 Uiso 1 1 calc R . . . .
C13 C -0.0106(12) 1.1168(10) 0.2356(10) 0.093(3) Uani 1 1 d . . . . .
H13 H -0.027259 1.220612 0.232638 0.112 Uiso 1 1 calc R . . . .
O5 O 0.2693(6) 0.2554(6) 0.2443(5) 0.0821(17) Uani 1 1 d . U . . .
N3 N 0.3752(10) 0.0066(9) 0.3381(10) 0.125(4) Uani 1 1 d . . . . .
C17 C 0.4389(13) -0.0667(12) 0.2503(10) 0.137(3) Uani 1 1 d . . . . .
H17A H 0.554832 -0.116158 0.243702 0.205 Uiso 1 1 calc GR . . . .
H17B H 0.406233 0.012417 0.187392 0.205 Uiso 1 1 calc GR . . . .
H17C H 0.398717 -0.146076 0.260209 0.205 Uiso 1 1 calc GR . . . .
C16 C 0.2914(15) 0.1610(14) 0.3314(12) 0.137(3) Uani 1 1 d . U . . .
H16 H 0.248018 0.200340 0.392771 0.164 Uiso 1 1 calc R . . . .
C18 C 0.4094(15) -0.0940(14) 0.4408(11) 0.137(3) Uani 1 1 d . . . . .
H18A H 0.361755 -0.169279 0.458131 0.205 Uiso 1 1 calc GR . . . .
H18B H 0.364776 -0.029328 0.492536 0.205 Uiso 1 1 calc GR . . . .
H18C H 0.524344 -0.150181 0.439920 0.205 Uiso 1 1 calc GR . . . .
O6 O -0.1467(6) 0.7446(5) 0.1337(4) 0.0578(12) Uani 1 1 d . . . . .
O7A O -0.076(3) 0.506(2) 0.1153(16) 0.115(8) Uani 0.5 1 d . . P A 1
N4 N -0.1929(9) 0.6624(8) 0.1095(6) 0.076(2) Uani 1 1 d . . . . .
O8 O -0.2955(13) 0.7250(9) 0.0523(8) 0.169(5) Uani 1 1 d . . . . .
O7B O -0.1583(16) 0.5217(16) 0.1605(10) 0.051(3) Uani 0.5 1 d . . P 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 O1 2.336(3) 2_566 ?
Bi1 O3 2.326(3) . ?
Bi1 O4 2.590(4) . ?
Bi1 C1 2.828(4) 2_566 ?
Bi1 O2 2.657(4) 2_566 ?
Bi1 C5 2.811(5) . ?
Bi1 N2 2.409(4) . ?
Bi1 N1 2.506(4) . ?
Bi1 O5 2.598(5) . ?
Bi1 O6 2.544(4) . ?
Bi1 O7A 2.742(18) . ?
O1 C1 1.265(6) . ?
O3 C5 1.267(5) . ?
C3 C2 1.389(6) . ?
C3 C4 1.385(6) . ?
C3 C5 1.498(6) . ?
C2 C4 1.383(6) 2_666 ?
C2 C1 1.506(6) . ?
O4 C5 1.220(6) . ?
C4 H4 0.9300 . ?
C1 O2 1.228(6) . ?
N2 C11 1.350(7) . ?
N2 C15 1.316(8) . ?
N1 C10 1.330(7) . ?
N1 C6 1.332(7) . ?
C11 C10 1.463(9) . ?
C11 C12 1.376(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(9) . ?
C9 C8 1.362(12) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(9) . ?
C7 C8 1.296(12) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.379(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.352(12) . ?
C14 H14 0.9300 . ?
C14 C13 1.347(13) . ?
C13 H13 0.9300 . ?
O5 C16 1.246(14) . ?
N3 C17 1.415(14) . ?
N3 C16 1.316(13) . ?
N3 C18 1.444(15) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O6 N4 1.210(7) . ?
O7A N4 1.39(2) . ?
N4 O8 1.207(8) . ?
N4 O7B 1.252(15) . ?

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
O1 Bi1 O4 129.00(12) 2_566 . ?
O1 Bi1 C1 26.21(12) 2_566 2_566 ?
O1 Bi1 O2 51.71(11) 2_566 2_566 ?
O1 Bi1 C5 104.79(13) 2_566 . ?
O1 Bi1 N2 81.76(14) 2_566 . ?
O1 Bi1 N1 136.75(14) 2_566 . ?
O1 Bi1 O5 125.66(15) 2_566 . ?
O1 Bi1 O6 73.44(14) 2_566 . ?
O1 Bi1 O7A 90.3(5) 2_566 . ?
O3 Bi1 O1 79.87(12) . 2_566 ?
O3 Bi1 O4 52.14(11) . . ?
O3 Bi1 C1 79.86(12) . 2_566 ?
O3 Bi1 O2 78.53(13) . 2_566 ?
O3 Bi1 C5 26.46(13) . . ?
O3 Bi1 N2 78.67(15) . . ?
O3 Bi1 N1 118.81(13) . . ?
O3 Bi1 O5 87.30(18) . . ?
O3 Bi1 O6 142.47(15) . . ?
O3 Bi1 O7A 158.8(4) . . ?
O4 Bi1 C1 131.40(12) . 2_566 ?
O4 Bi1 O2 121.16(13) . 2_566 ?
O4 Bi1 C5 25.69(12) . . ?
O4 Bi1 O5 73.78(17) . . ?
O4 Bi1 O7A 140.7(5) . . ?
O2 Bi1 C1 25.63(12) 2_566 2_566 ?
O2 Bi1 C5 100.87(13) 2_566 . ?
O2 Bi1 O7A 80.6(4) 2_566 . ?
C5 Bi1 C1 106.14(13) . 2_566 ?
N2 Bi1 O4 73.67(15) . . ?
N2 Bi1 C1 107.35(15) . 2_566 ?
N2 Bi1 O2 130.91(14) . 2_566 ?
N2 Bi1 C5 73.94(16) . . ?
N2 Bi1 N1 66.32(16) . . ?
N2 Bi1 O5 146.59(17) . . ?
N2 Bi1 O6 71.88(16) . . ?
N2 Bi1 O7A 118.7(4) . . ?
N1 Bi1 O4 70.14(13) . . ?
N1 Bi1 C1 156.57(14) . 2_566 ?
N1 Bi1 O2 159.87(14) . 2_566 ?
N1 Bi1 C5 93.97(14) . . ?
N1 Bi1 O5 95.49(18) . . ?
N1 Bi1 O6 69.44(15) . . ?
N1 Bi1 O7A 81.1(4) . . ?
O5 Bi1 C1 99.67(16) . 2_566 ?
O5 Bi1 O2 74.04(15) . 2_566 ?
O5 Bi1 C5 80.02(18) . . ?
O5 Bi1 O7A 83.2(5) . . ?
O6 Bi1 O4 134.61(14) . . ?
O6 Bi1 C1 87.13(14) . 2_566 ?
O6 Bi1 O2 103.71(14) . 2_566 ?
O6 Bi1 C5 145.67(15) . . ?
O6 Bi1 O5 129.77(19) . . ?
O6 Bi1 O7A 48.0(5) . . ?
O7A Bi1 C1 83.1(5) . 2_566 ?
O7A Bi1 C5 162.0(5) . . ?
C1 O1 Bi1 99.1(3) . 2_566 ?
C5 O3 Bi1 98.6(3) . . ?
C2 C3 C5 121.8(4) . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 C5 118.3(4) . . ?
C3 C2 C1 124.7(4) . . ?
C4 C2 C3 118.9(4) 2_666 . ?
C4 C2 C1 116.3(4) 2_666 . ?
C5 O4 Bi1 87.3(3) . . ?
C3 C4 H4 119.4 . . ?
C2 C4 C3 121.2(4) 2_666 . ?
C2 C4 H4 119.4 2_666 . ?
O1 C1 Bi1 54.7(2) . 2_566 ?
O1 C1 C2 116.6(4) . . ?
C2 C1 Bi1 163.4(3) . 2_566 ?
O2 C1 Bi1 69.4(3) . 2_566 ?
O2 C1 O1 123.6(4) . . ?
O2 C1 C2 119.4(4) . . ?
C1 O2 Bi1 85.0(3) . 2_566 ?
O3 C5 Bi1 54.9(2) . . ?
O3 C5 C3 117.9(4) . . ?
C3 C5 Bi1 171.9(3) . . ?
O4 C5 Bi1 67.0(3) . . ?
O4 C5 O3 121.8(4) . . ?
O4 C5 C3 120.3(4) . . ?
C11 N2 Bi1 120.8(4) . . ?
C15 N2 Bi1 119.9(4) . . ?
C15 N2 C11 119.3(5) . . ?
C10 N1 Bi1 118.3(4) . . ?
C10 N1 C6 120.4(5) . . ?
C6 N1 Bi1 121.1(4) . . ?
N2 C11 C10 117.4(5) . . ?
N2 C11 C12 119.2(6) . . ?
C12 C11 C10 123.4(6) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(8) . . ?
N1 C10 C11 117.0(5) . . ?
N1 C10 C9 118.2(6) . . ?
C9 C10 C11 124.8(6) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C8 C7 C6 118.9(8) . . ?
N1 C6 C7 121.4(7) . . ?
N1 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.8(7) . . ?
C7 C8 H8 119.6 . . ?
N2 C15 H15 118.6 . . ?
N2 C15 C14 122.9(8) . . ?
C14 C15 H15 118.6 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(8) . . ?
C13 C12 H12 119.6 . . ?
C15 C14 H14 121.0 . . ?
C13 C14 C15 117.9(8) . . ?
C13 C14 H14 121.0 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(7) . . ?
C14 C13 H13 120.1 . . ?
C16 O5 Bi1 115.8(7) . . ?
C17 N3 C18 117.8(9) . . ?
C16 N3 C17 124.1(12) . . ?
C16 N3 C18 118.1(12) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C16 N3 121.2(13) . . ?
O5 C16 H16 119.4 . . ?
N3 C16 H16 119.4 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 O6 Bi1 104.6(4) . . ?
N4 O7A Bi1 90.2(9) . . ?
O6 N4 O7A 111.7(9) . . ?
O6 N4 O7B 118.7(8) . . ?
O8 N4 O6 119.1(7) . . ?
O8 N4 O7A 123.8(10) . . ?
O8 N4 O7B 120.5(9) . . ?

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
Bi1 O1 C1 C2 163.6(3) 2_566 . . . ?
Bi1 O1 C1 O2 -8.8(5) 2_566 . . . ?
Bi1 O3 C5 C3 175.6(4) . . . . ?
Bi1 O3 C5 O4 -2.7(6) . . . . ?
Bi1 O4 C5 O3 2.4(5) . . . . ?
Bi1 O4 C5 C3 -175.9(4) . . . . ?
Bi1 N2 C11 C10 -3.4(7) . . . . ?
Bi1 N2 C11 C12 177.4(5) . . . . ?
Bi1 N2 C15 C14 -178.6(6) . . . . ?
Bi1 N1 C10 C11 -4.1(7) . . . . ?
Bi1 N1 C10 C9 175.5(5) . . . . ?
Bi1 N1 C6 C7 -174.8(5) . . . . ?
Bi1 O5 C16 N3 171.9(9) . . . . ?
Bi1 O6 N4 O7A -24.1(12) . . . . ?
Bi1 O6 N4 O8 -179.1(9) . . . . ?
Bi1 O6 N4 O7B 15.3(11) . . . . ?
Bi1 O7A N4 O6 21.5(10) . . . . ?
Bi1 O7A N4 O8 175.1(10) . . . . ?
O1 C1 O2 Bi1 7.6(5) . . . 2_566 ?
C3 C2 C1 Bi1 143.2(9) . . . 2_566 ?
C3 C2 C1 O1 89.1(6) . . . . ?
C3 C2 C1 O2 -98.2(6) . . . . ?
C2 C3 C4 C2 0.4(8) . . . 2_666 ?
C2 C3 C5 O3 -3.8(7) . . . . ?
C2 C3 C5 O4 174.6(5) . . . . ?
C2 C1 O2 Bi1 -164.5(4) . . . 2_566 ?
C4 C3 C2 C4 -0.4(8) . . . 2_666 ?
C4 C3 C2 C1 -179.9(4) . . . . ?
C4 C3 C5 O3 179.1(5) . . . . ?
C4 C3 C5 O4 -2.6(7) . . . . ?
C4 C2 C1 Bi1 -36.3(13) 2_666 . . 2_566 ?
C4 C2 C1 O1 -90.4(5) 2_666 . . . ?
C4 C2 C1 O2 82.3(6) 2_666 . . . ?
C5 C3 C2 C4 -177.5(4) . . . 2_666 ?
C5 C3 C2 C1 3.0(7) . . . . ?
C5 C3 C4 C2 177.6(4) . . . 2_666 ?
N2 C11 C10 N1 5.0(8) . . . . ?
N2 C11 C10 C9 -174.6(6) . . . . ?
N2 C11 C12 C13 2.0(11) . . . . ?
N2 C15 C14 C13 0.6(13) . . . . ?
C11 N2 C15 C14 1.1(11) . . . . ?
C11 C12 C13 C14 -0.3(14) . . . . ?
C10 N1 C6 C7 0.9(9) . . . . ?
C10 C11 C12 C13 -177.1(7) . . . . ?
C10 C9 C8 C7 -1.2(15) . . . . ?
C6 N1 C10 C11 -180.0(5) . . . . ?
C6 N1 C10 C9 -0.4(9) . . . . ?
C6 C7 C8 C9 1.7(15) . . . . ?
C8 C9 C10 N1 0.5(12) . . . . ?
C8 C9 C10 C11 -179.9(8) . . . . ?
C8 C7 C6 N1 -1.6(12) . . . . ?
C15 N2 C11 C10 176.8(6) . . . . ?
C15 N2 C11 C12 -2.3(9) . . . . ?
C15 C14 C13 C12 -1.0(15) . . . . ?
C12 C11 C10 N1 -175.9(6) . . . . ?
C12 C11 C10 C9 4.5(10) . . . . ?
C17 N3 C16 O5 -4(2) . . . . ?
C18 N3 C16 O5 174.1(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.718
_exptl_crystal_recrystallization_method Hydrothermal
####################################################################### 
# 
# 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_zn4r3
_database_code_depnum_ccdc_archive 'CCDC 1561411'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2016-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 N2 O5 Zn'
_chemical_formula_sum            'C15 H11 N2 O5 Zn'
_chemical_formula_weight         364.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 N2 H10 O10 Zn'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6958(6)
_cell_length_b                   8.8864(7)
_cell_length_c                   10.6748(9)
_cell_angle_alpha                80.941(7)
_cell_angle_beta                 70.420(8)
_cell_angle_gamma                78.138(7)
_cell_volume                     670.01(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0340
_cell_measurement_theta_min      2.4250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90986
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         34.267
_diffrn_reflns_theta_min         2.848
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 110.00   1.00   50.00    --   27.63  54.00   0.00  180
  2  ω    -70.00 110.00   1.00   50.00    --   27.63  54.00 120.00  180
  3  ω    -70.00 110.00   1.00   50.00    --   27.63  54.00 240.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0146983000
_diffrn_orient_matrix_UB_12      -0.0609556000
_diffrn_orient_matrix_UB_13      0.0520385000
_diffrn_orient_matrix_UB_21      -0.0367712000
_diffrn_orient_matrix_UB_22      -0.0376523000
_diffrn_orient_matrix_UB_23      -0.0369674000
_diffrn_orient_matrix_UB_31      0.0909207000
_diffrn_orient_matrix_UB_32      -0.0397575000
_diffrn_orient_matrix_UB_33      -0.0307481000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3706
_reflns_number_total             5108
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.2873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C6(H6), C9(H9), C7(H7), C8(H8), C14(H14), C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Zn1 Zn 0.68213(3) 0.63295(3) 0.78246(2) 0.02279(8) Uani 1 1 d . . . . .
O1 O 0.4282(2) 0.71255(19) 0.89632(16) 0.0302(3) Uani 1 1 d . . . . .
O4 O -0.1938(2) 0.79482(19) 0.82181(17) 0.0337(4) Uani 1 1 d . . . . .
O2 O 0.3782(3) 0.8518(2) 0.71837(17) 0.0450(5) Uani 1 1 d . . . . .
N1 N 0.7884(3) 0.6872(2) 0.57760(17) 0.0252(4) Uani 1 1 d . . . . .
O5 O 0.7711(3) 0.4751(2) 0.9170(2) 0.0448(5) Uani 1 1 d . . . . .
O3 O 0.0555(2) 0.6417(2) 0.8582(2) 0.0474(5) Uani 1 1 d . . . . .
N2 N 0.6424(3) 0.4407(2) 0.70046(19) 0.0293(4) Uani 1 1 d . . . . .
C3 C -0.0220(3) 0.8919(2) 0.92723(19) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.1564(3) 0.9030(2) 0.92665(19) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.1755(3) 1.0102(2) 1.0002(2) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.2942 1.0169 1.0011 0.025 Uiso 1 1 calc R . . . .
C1 C 0.3317(3) 0.8151(2) 0.8376(2) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.7832(3) 0.5875(2) 0.4979(2) 0.0242(4) Uani 1 1 d . . . . .
C4 C -0.0534(3) 0.7662(2) 0.8624(2) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.7032(3) 0.4476(3) 0.5669(2) 0.0253(4) Uani 1 1 d . . . . .
C12 C 0.6888(3) 0.3318(3) 0.4998(2) 0.0326(5) Uani 1 1 d . . . . .
H12 H 0.7301 0.3392 0.4069 0.039 Uiso 1 1 calc R . . . .
C6 C 0.8521(4) 0.8184(3) 0.5230(2) 0.0333(5) Uani 1 1 d . . . . .
H6 H 0.8550 0.8874 0.5791 0.040 Uiso 1 1 calc R . . . .
C9 C 0.8491(4) 0.6158(3) 0.3602(2) 0.0338(5) Uani 1 1 d . . . . .
H9 H 0.8491 0.5438 0.3056 0.041 Uiso 1 1 calc R . . . .
C7 C 0.9137(4) 0.8564(3) 0.3874(3) 0.0389(6) Uani 1 1 d . . . . .
H7 H 0.9537 0.9505 0.3522 0.047 Uiso 1 1 calc R . . . .
C8 C 0.9147(4) 0.7521(3) 0.3054(2) 0.0386(6) Uani 1 1 d . . . . .
H8 H 0.9594 0.7733 0.2131 0.046 Uiso 1 1 calc R . . . .
C14 C 0.5560(4) 0.1969(3) 0.7089(3) 0.0436(6) Uani 1 1 d . . . . .
H14 H 0.5073 0.1112 0.7597 0.052 Uiso 1 1 calc R . . . .
C13 C 0.6130(4) 0.2062(3) 0.5721(3) 0.0381(6) Uani 1 1 d . . . . .
H13 H 0.6004 0.1280 0.5288 0.046 Uiso 1 1 calc R . . . .
C15 C 0.5721(4) 0.3163(3) 0.7692(3) 0.0404(6) Uani 1 1 d . . . . .
H15 H 0.5324 0.3102 0.8620 0.048 Uiso 1 1 calc R . . . .
H5A H 0.709(5) 0.427(4) 0.973(4) 0.067(12) Uiso 1 1 d . . . . .
H5B H 0.858(5) 0.491(4) 0.935(4) 0.069(12) Uiso 1 1 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
Zn1 O1 1.9768(15) . ?
Zn1 O4 2.0447(15) 1_655 ?
Zn1 N1 2.0773(18) . ?
Zn1 O5 2.032(2) . ?
Zn1 N2 2.1552(19) . ?
O1 C1 1.276(3) . ?
O4 Zn1 2.0447(15) 1_455 ?
O4 C4 1.259(3) . ?
O2 C1 1.211(3) . ?
N1 C10 1.336(3) . ?
N1 C6 1.329(3) . ?
O5 H5A 0.77(4) . ?
O5 H5B 0.80(4) . ?
O3 C4 1.240(3) . ?
N2 C11 1.339(3) . ?
N2 C15 1.333(3) . ?
C3 C2 1.394(3) . ?
C3 C5 1.389(3) 2_577 ?
C3 C4 1.500(3) . ?
C2 C5 1.385(3) . ?
C2 C1 1.508(3) . ?
C5 C3 1.389(3) 2_577 ?
C5 H5 0.9300 . ?
C10 C11 1.479(3) . ?
C10 C9 1.385(3) . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(4) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.371(4) . ?
C14 C15 1.371(4) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?

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
O1 Zn1 O4 94.84(7) . 1_655 ?
O1 Zn1 N1 125.35(7) . . ?
O1 Zn1 O5 99.92(8) . . ?
O1 Zn1 N2 103.69(7) . . ?
O4 Zn1 N1 92.09(7) 1_655 . ?
O4 Zn1 N2 161.46(7) 1_655 . ?
N1 Zn1 N2 76.72(7) . . ?
O5 Zn1 O4 90.62(8) . 1_655 ?
O5 Zn1 N1 134.17(9) . . ?
O5 Zn1 N2 86.90(8) . . ?
C1 O1 Zn1 115.16(13) . . ?
C4 O4 Zn1 125.35(15) . 1_455 ?
C10 N1 Zn1 117.53(15) . . ?
C6 N1 Zn1 123.34(15) . . ?
C6 N1 C10 119.05(19) . . ?
Zn1 O5 H5A 125(3) . . ?
Zn1 O5 H5B 117(3) . . ?
H5A O5 H5B 112(4) . . ?
C11 N2 Zn1 114.89(15) . . ?
C15 N2 Zn1 126.52(16) . . ?
C15 N2 C11 118.5(2) . . ?
C2 C3 C4 121.28(17) . . ?
C5 C3 C2 119.36(17) 2_577 . ?
C5 C3 C4 119.08(18) 2_577 . ?
C3 C2 C1 122.59(17) . . ?
C5 C2 C3 119.01(18) . . ?
C5 C2 C1 118.07(18) . . ?
C3 C5 H5 119.2 2_577 . ?
C2 C5 C3 121.62(18) . 2_577 ?
C2 C5 H5 119.2 . . ?
O1 C1 C2 116.25(18) . . ?
O2 C1 O1 124.4(2) . . ?
O2 C1 C2 119.1(2) . . ?
N1 C10 C11 115.54(18) . . ?
N1 C10 C9 121.2(2) . . ?
C9 C10 C11 123.2(2) . . ?
O4 C4 C3 116.64(19) . . ?
O3 C4 O4 125.6(2) . . ?
O3 C4 C3 117.67(19) . . ?
N2 C11 C10 115.29(18) . . ?
N2 C11 C12 121.5(2) . . ?
C12 C11 C10 123.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
N1 C6 H6 118.6 . . ?
N1 C6 C7 122.8(2) . . ?
C7 C6 H6 118.6 . . ?
C10 C9 H9 120.6 . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 120.6 . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.3(2) . . ?
C8 C7 H7 120.9 . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.7(2) . . ?
C15 C14 H14 120.7 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N2 C15 C14 122.8(2) . . ?
N2 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?

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
Zn1 O1 C1 O2 8.1(3) . . . . ?
Zn1 O1 C1 C2 -166.88(13) . . . . ?
Zn1 O4 C4 O3 16.3(3) 1_455 . . . ?
Zn1 O4 C4 C3 -160.54(14) 1_455 . . . ?
Zn1 N1 C10 C11 -0.8(2) . . . . ?
Zn1 N1 C10 C9 179.23(17) . . . . ?
Zn1 N1 C6 C7 -176.77(19) . . . . ?
Zn1 N2 C11 C10 -1.4(2) . . . . ?
Zn1 N2 C11 C12 179.37(17) . . . . ?
Zn1 N2 C15 C14 -178.3(2) . . . . ?
N1 C10 C11 N2 1.4(3) . . . . ?
N1 C10 C11 C12 -179.3(2) . . . . ?
N1 C10 C9 C8 -2.4(3) . . . . ?
N1 C6 C7 C8 -2.1(4) . . . . ?
N2 C11 C12 C13 -1.0(4) . . . . ?
C3 C2 C5 C3 -1.0(3) . . . 2_577 ?
C3 C2 C1 O1 -114.5(2) . . . . ?
C3 C2 C1 O2 70.3(3) . . . . ?
C2 C3 C4 O4 -153.5(2) . . . . ?
C2 C3 C4 O3 29.4(3) . . . . ?
C5 C3 C2 C5 0.9(3) 2_577 . . . ?
C5 C3 C2 C1 -172.33(19) 2_577 . . . ?
C5 C3 C4 O4 32.5(3) 2_577 . . . ?
C5 C3 C4 O3 -144.6(2) 2_577 . . . ?
C5 C2 C1 O1 72.2(3) . . . . ?
C5 C2 C1 O2 -103.0(2) . . . . ?
C1 C2 C5 C3 172.62(19) . . . 2_577 ?
C10 N1 C6 C7 -0.2(4) . . . . ?
C10 C11 C12 C13 179.9(2) . . . . ?
C10 C9 C8 C7 0.1(4) . . . . ?
C4 C3 C2 C5 -172.97(18) . . . . ?
C4 C3 C2 C1 13.8(3) . . . . ?
C11 N2 C15 C14 -1.4(4) . . . . ?
C11 C10 C9 C8 177.6(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C6 N1 C10 C11 -177.6(2) . . . . ?
C6 N1 C10 C9 2.4(3) . . . . ?
C6 C7 C8 C9 2.1(4) . . . . ?
C9 C10 C11 N2 -178.5(2) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C13 C14 C15 N2 -0.6(4) . . . . ?
C15 N2 C11 C10 -178.6(2) . . . . ?
C15 N2 C11 C12 2.2(3) . . . . ?
C15 C14 C13 C12 1.8(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.131
_oxdiff_exptl_absorpt_empirical_full_min 0.890
_exptl_crystal_recrystallization_method Hydrothermal
####################################################################### 
# 
# 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_Bi13
_database_code_depnum_ccdc_archive 'CCDC 1561410'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Bi N2 O8'
_chemical_formula_sum            'C8 H11 Bi N2 O8'
_chemical_formula_weight         472.17
_chemical_melting_point          ?
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.337(5)
_cell_length_b                   12.223(3)
_cell_length_c                   10.707(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.479(9)
_cell_angle_gamma                90
_cell_volume                     2323.6(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.217
_exptl_absorpt_correction_T_max  0.527
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.699
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2604
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.271
_diffrn_reflns_theta_min         2.023
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -70.0000 - 110.0000
	     Image width: 1.0000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 50.3266
	          2theta: 27.5575
scan:
	Number of images: 180
	           Slice: -70.0000 - 110.0000
	     Image width: 1.0000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 50.3266
	          2theta: 27.5575
scan:
	Number of images: 180
	           Slice: -70.0000 - 110.0000
	     Image width: 1.0000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 50.3266
	          2theta: 27.5575
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.052698
_diffrn_orient_matrix_UB_12      0.006464
_diffrn_orient_matrix_UB_13      -0.018802
_diffrn_orient_matrix_UB_21      -0.013916
_diffrn_orient_matrix_UB_22      0.055807
_diffrn_orient_matrix_UB_23      0.058187
_diffrn_orient_matrix_UB_31      0.006324
_diffrn_orient_matrix_UB_32      0.070217
_diffrn_orient_matrix_UB_33      -0.065832
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2154
_reflns_number_total             2604
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.940
_refine_diff_density_min         -1.768
_refine_diff_density_rms         0.178
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+1.7249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C3(H3A,H3B), C2(H2C,H2D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.67631(2) 0.75556(2) 0.60718(2) 0.02165(9) Uani 1 1 d . . . . .
O5 O 0.6507(3) 0.7684(3) 0.8168(4) 0.0339(10) Uani 1 1 d . . . . .
O3 O 0.7071(2) 0.6296(3) 0.4701(4) 0.0300(9) Uani 1 1 d . . . . .
N2 N 0.6089(2) 0.8131(4) 1.0293(4) 0.0275(11) Uani 1 1 d . . . . .
H2A H 0.659010 0.815201 1.052729 0.033 Uiso 1 1 calc R . . . .
H2B H 0.595548 0.745537 1.001916 0.033 Uiso 1 1 calc R . . . .
O4 O 0.7539(2) 0.4650(4) 0.4510(4) 0.0426(11) Uani 1 1 d . . . . .
C4 C 0.7237(3) 0.5307(5) 0.5080(5) 0.0269(13) Uani 1 1 d . . . . .
C5 C 0.6134(3) 0.8575(5) 0.8075(6) 0.0283(13) Uani 1 1 d . . . . .
C6 C 0.5826(3) 0.8893(4) 0.9201(5) 0.0280(13) Uani 1 1 d . . . . .
H6A H 0.598631 0.962996 0.947298 0.034 Uiso 1 1 calc R . . . .
H6B H 0.527947 0.888539 0.893880 0.034 Uiso 1 1 calc R . . . .
O6 O 0.6011(3) 0.9183(3) 0.7120(4) 0.0436(12) Uani 1 1 d . . . . .
C7 C 0.5804(3) 0.8346(5) 1.1448(5) 0.0296(14) Uani 1 1 d . . . . .
H7A H 0.537777 0.787232 1.143385 0.036 Uiso 1 1 calc R . . . .
H7B H 0.563172 0.909810 1.142886 0.036 Uiso 1 1 calc R . . . .
O1 O 0.5552(2) 0.7101(4) 0.5429(4) 0.0407(11) Uani 1 1 d . . . . .
C1 C 0.5309(3) 0.6261(5) 0.5886(6) 0.0300(13) Uani 1 1 d . . . . .
C3 C 0.7083(4) 0.4975(5) 0.6338(6) 0.0337(14) Uani 1 1 d . . . . .
H3A H 0.681019 0.428691 0.621549 0.040 Uiso 1 1 calc R . . . .
H3B H 0.755960 0.484994 0.696101 0.040 Uiso 1 1 calc R . . . .
C2 C 0.5863(3) 0.5493(5) 0.6746(7) 0.0371(15) Uani 1 1 d . . . . .
H2C H 0.576684 0.549090 0.759618 0.045 Uiso 1 1 calc R . . . .
H2D H 0.577560 0.475768 0.640088 0.045 Uiso 1 1 calc R . . . .
O8 O 0.7041(2) 0.7887(4) 1.2506(4) 0.0320(9) Uani 1 1 d . . . . .
O7 O 0.6236(2) 0.8297(4) 1.3692(4) 0.0387(11) Uani 1 1 d . . . . .
C8 C 0.6405(3) 0.8153(4) 1.2672(6) 0.0271(13) Uani 1 1 d . . . . .
N1 N 0.6649(2) 0.5775(4) 0.6874(4) 0.0239(10) Uani 1 1 d . . . . .
H1 H 0.688399 0.580384 0.780224 0.029 Uiso 1 1 calc R . . . .
O2 O 0.4624(2) 0.6072(4) 0.5687(5) 0.0452(12) Uani 1 1 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 O5 2.411(4) . ?
Bi1 O3 2.293(4) . ?
Bi1 O1 2.224(4) . ?
Bi1 O8 2.398(4) 7_667 ?
Bi1 O7 2.649(4) 1_554 ?
Bi1 N1 2.369(4) . ?
O5 C5 1.277(7) . ?
O3 C4 1.287(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C6 1.478(6) . ?
N2 C7 1.482(6) . ?
O4 C4 1.222(7) . ?
C4 C3 1.500(8) . ?
C5 C6 1.505(7) . ?
C5 O6 1.238(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.505(7) . ?
O1 C1 1.266(7) . ?
C1 C2 1.514(8) . ?
C1 O2 1.243(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 N1 1.464(7) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C2 N1 1.455(7) . ?
O8 C8 1.265(7) . ?
O7 C8 1.220(7) . ?
N1 H1 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 O7 139.81(13) . 1_554 ?
O3 Bi1 O5 140.92(13) . . ?
O3 Bi1 O8 85.54(14) . 7_667 ?
O3 Bi1 O7 72.73(13) . 1_554 ?
O3 Bi1 N1 70.93(14) . . ?
O1 Bi1 O5 83.82(16) . . ?
O1 Bi1 O3 91.20(17) . . ?
O1 Bi1 O8 145.47(15) . 7_667 ?
O1 Bi1 O7 72.03(14) . 1_554 ?
O1 Bi1 N1 73.22(16) . . ?
O8 Bi1 O5 77.52(14) 7_667 . ?
O8 Bi1 O7 138.07(13) 7_667 1_554 ?
N1 Bi1 O5 70.53(14) . . ?
N1 Bi1 O8 73.25(15) . 7_667 ?
N1 Bi1 O7 128.26(15) . 1_554 ?
C5 O5 Bi1 102.0(4) . . ?
C4 O3 Bi1 120.3(4) . . ?
H2A N2 H2B 107.4 . . ?
C6 N2 H2A 108.3 . . ?
C6 N2 H2B 108.3 . . ?
C6 N2 C7 115.7(4) . . ?
C7 N2 H2A 108.3 . . ?
C7 N2 H2B 108.3 . . ?
O3 C4 C3 117.1(5) . . ?
O4 C4 O3 124.1(6) . . ?
O4 C4 C3 118.7(5) . . ?
O5 C5 C6 117.3(5) . . ?
O6 C5 O5 124.0(5) . . ?
O6 C5 C6 118.7(5) . . ?
N2 C6 C5 110.9(4) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
N2 C7 C8 111.4(5) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C1 O1 Bi1 120.2(4) . . ?
O1 C1 C2 119.4(5) . . ?
O2 C1 O1 121.6(6) . . ?
O2 C1 C2 119.0(6) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C3 C4 114.4(5) . . ?
N1 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
C1 C2 H2C 108.7 . . ?
C1 C2 H2D 108.7 . . ?
H2C C2 H2D 107.6 . . ?
N1 C2 C1 114.2(5) . . ?
N1 C2 H2C 108.7 . . ?
N1 C2 H2D 108.7 . . ?
C8 O8 Bi1 134.2(4) . 7_667 ?
C8 O7 Bi1 134.2(4) . 1_556 ?
O8 C8 C7 114.7(5) . . ?
O7 C8 C7 117.5(5) . . ?
O7 C8 O8 127.8(5) . . ?
Bi1 N1 H1 106.1 . . ?
C3 N1 Bi1 111.5(3) . . ?
C3 N1 H1 106.1 . . ?
C2 N1 Bi1 111.0(3) . . ?
C2 N1 C3 115.3(5) . . ?
C2 N1 H1 106.1 . . ?

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
Bi1 O5 C5 C6 176.0(4) . . . . ?
Bi1 O5 C5 O6 -3.7(7) . . . . ?
Bi1 O3 C4 O4 -165.8(4) . . . . ?
Bi1 O3 C4 C3 10.9(7) . . . . ?
Bi1 O1 C1 C2 -7.4(7) . . . . ?
Bi1 O1 C1 O2 169.7(4) . . . . ?
Bi1 O8 C8 C7 -179.4(4) 7_667 . . . ?
Bi1 O8 C8 O7 3.0(10) 7_667 . . . ?
Bi1 O7 C8 C7 156.1(4) 1_556 . . . ?
Bi1 O7 C8 O8 -26.3(10) 1_556 . . . ?
O5 C5 C6 N2 5.8(7) . . . . ?
O3 C4 C3 N1 9.3(8) . . . . ?
N2 C7 C8 O8 2.6(7) . . . . ?
N2 C7 C8 O7 -179.6(5) . . . . ?
O4 C4 C3 N1 -173.8(5) . . . . ?
C4 C3 N1 Bi1 -23.1(6) . . . . ?
C4 C3 N1 C2 104.6(6) . . . . ?
C6 N2 C7 C8 -141.1(5) . . . . ?
O6 C5 C6 N2 -174.5(5) . . . . ?
C7 N2 C6 C5 -178.5(5) . . . . ?
O1 C1 C2 N1 -4.7(8) . . . . ?
C1 C2 N1 Bi1 13.0(6) . . . . ?
C1 C2 N1 C3 -114.9(6) . . . . ?
O2 C1 C2 N1 178.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Hydrothermal
