# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_bif-89
_database_code_depnum_ccdc_archive 'CCDC 1584142'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 B Cd N8 O5'
_chemical_formula_weight         535.59

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'
B B 0.0013 0.0007 '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'
Cd Cd -0.8075 1.2024 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2198(5)
_cell_length_b                   14.0236(8)
_cell_length_c                   15.7941(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.723(5)
_cell_angle_gamma                90
_cell_volume                     1965.69(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2679
_cell_measurement_theta_min      3.0290
_cell_measurement_theta_max      27.6110

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.162
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.848
_oxdiff_exptl_absorpt_empirical_full_max 1.165
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2083
_diffrn_reflns_number            7230
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3454
_reflns_number_gt                2919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.3235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Cd1 Cd 0.87705(2) 0.33613(2) 0.22395(2) 0.01748(9) Uani 1 1 d . . . . .
N6 N 0.6692(3) 0.5479(2) 0.36848(15) 0.0176(6) Uani 1 1 d . . . . .
O4 O 0.6765(3) 0.3669(2) -0.14084(16) 0.0471(8) Uani 1 1 d . . . . .
C4 C 0.8785(4) 0.6570(3) 0.5828(2) 0.0217(8) Uani 1 1 d . . . . .
N7 N 0.3194(3) 0.7578(2) 0.37437(15) 0.0201(6) Uani 1 1 d . . . . .
O2 O 0.8770(2) 0.48579(18) 0.15009(14) 0.0279(6) Uani 1 1 d . . . . .
N3 N 0.9235(3) 0.6142(2) 0.65982(15) 0.0214(6) Uani 1 1 d . . . . .
C15 C 0.6368(4) 0.4640(2) 0.00046(19) 0.0203(8) Uani 1 1 d . . . . .
H15 H 0.7305 0.4391 0.0009 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5372(4) 0.5120(2) 0.3150(2) 0.0220(8) Uani 1 1 d . . . . .
H8 H 0.4410 0.5361 0.3091 0.026 Uiso 1 1 calc R U . . .
C10 C 0.4414(4) 0.7236(3) 0.3574(2) 0.0212(8) Uani 1 1 d . . . . .
O5 O 0.4450(3) 0.31262(19) -0.17835(15) 0.0350(7) Uani 1 1 d . . . . .
H5 H 0.3636 0.3271 -0.1703 0.053 Uiso 1 1 calc R U . . .
C12 C 0.3318(4) 0.7330(3) 0.46043(19) 0.0222(8) Uani 1 1 d . . . . .
H12 H 0.2616 0.7471 0.4913 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4628(4) 0.6848(3) 0.4931(2) 0.0199(8) Uani 1 1 d . . . . .
C13 C 0.7793(4) 0.5482(3) 0.1327(2) 0.0212(8) Uani 1 1 d . . . . .
O3 O 0.7992(3) 0.63238(19) 0.16231(17) 0.0394(7) Uani 1 1 d . . . . .
C6 C 0.8456(4) 0.5299(3) 0.6497(2) 0.0279(9) Uani 1 1 d . . . . .
N1 N 0.9536(3) 0.7962(2) 0.35484(17) 0.0240(7) Uani 1 1 d . . . . .
C5 C 0.7545(4) 0.5243(3) 0.5662(2) 0.0290(9) Uani 1 1 d . . . . .
N5 N 0.7258(3) 0.4208(2) 0.29783(17) 0.0244(7) Uani 1 1 d . . . . .
C1 C 0.8935(4) 0.7125(3) 0.3615(2) 0.0214(8) Uani 1 1 d . . . . .
C16 C 0.5131(3) 0.4368(2) -0.06691(18) 0.0184(7) Uani 1 1 d . . . . .
C14 C 0.6290(3) 0.5260(2) 0.06698(19) 0.0175(7) Uani 1 1 d . . . . .
O1 O 0.9052(4) 0.1879(2) 0.2926(2) 0.0437(8) Uani 1 1 d . . . . .
C9 C 0.5724(4) 0.4357(3) 0.2726(2) 0.0292(9) Uani 1 1 d . . . . .
H9 H 0.5031 0.3986 0.2323 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7692(4) 0.8118(3) 0.4191(2) 0.0285(9) Uani 1 1 d . . . . .
C17 C 0.5492(4) 0.3695(3) -0.1331(2) 0.0277(9) Uani 1 1 d . . . . .
C3 C 0.8756(4) 0.8594(3) 0.3921(2) 0.0314(9) Uani 1 1 d . . . . .
H3 H 0.8932 0.9247 0.3978 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7777(4) 0.4892(3) 0.3554(2) 0.0241(8) Uani 1 1 d . . . . .
H7 H 0.8794 0.4965 0.3843 0.029 Uiso 1 1 calc R U . . .
B35 B 0.6892(4) 0.6357(3) 0.4286(2) 0.0159(8) Uani 1 1 d . . . . .
N1AA N 0.7797(3) 0.71671(19) 0.39946(15) 0.0165(6) Uani 1 1 d . . . . .
N2AA N 0.7748(3) 0.60596(19) 0.52331(15) 0.0162(6) Uani 1 1 d . . . . .
N0AA N 0.5336(3) 0.67806(19) 0.42665(15) 0.0159(6) Uani 1 1 d . . . . .
H2 H 0.700(4) 0.833(2) 0.446(2) 0.019(9) Uiso 1 1 d . . . . .
H1 H 0.918(4) 0.652(3) 0.340(2) 0.036(11) Uiso 1 1 d . . . . .
H10 H 0.467(3) 0.730(2) 0.305(2) 0.022(9) Uiso 1 1 d . . . . .
H11 H 0.505(4) 0.657(2) 0.546(2) 0.024(9) Uiso 1 1 d . . . . .
H5A H 0.684(4) 0.476(3) 0.538(2) 0.034(10) Uiso 1 1 d . . . . .
H4 H 0.910(3) 0.717(2) 0.5719(17) 0.007(8) Uiso 1 1 d . . . . .
H6 H 0.854(3) 0.478(2) 0.6966(19) 0.021(9) Uiso 1 1 d . . . . .
H1A H 0.852(5) 0.171(3) 0.325(3) 0.063(17) Uiso 1 1 d . . . . .
H1B H 0.973(6) 0.166(4) 0.311(3) 0.06(2) 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
Cd1 N1 2.314(3) 2_745 ?
Cd1 N7 2.318(2) 2_645 ?
Cd1 O1 2.326(3) . ?
Cd1 N3 2.325(2) 3_766 ?
Cd1 N5 2.366(3) . ?
Cd1 O2 2.401(2) . ?
N6 C7 1.354(4) . ?
N6 C8 1.375(4) . ?
N6 B35 1.535(5) . ?
O4 C17 1.213(4) . ?
C4 N3 1.318(4) . ?
C4 N2AA 1.350(4) . ?
C4 H4 0.92(3) . ?
N7 C10 1.315(4) . ?
N7 C12 1.377(4) . ?
N7 Cd1 2.318(2) 2_655 ?
O2 C13 1.233(4) . ?
N3 C6 1.370(4) . ?
N3 Cd1 2.325(2) 3_766 ?
C15 C14 1.380(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C8 C9 1.347(5) . ?
C8 H8 0.9300 . ?
C10 N0AA 1.350(4) . ?
C10 H10 0.92(3) . ?
O5 C17 1.303(4) . ?
O5 H5 0.8200 . ?
C12 C11 1.359(5) . ?
C12 H12 0.9300 . ?
C11 N0AA 1.381(4) . ?
C11 H11 0.91(3) . ?
C13 O3 1.264(4) . ?
C13 C14 1.522(4) . ?
C6 C5 1.360(4) . ?
C6 H6 1.03(3) . ?
N1 C1 1.315(4) . ?
N1 C3 1.371(4) . ?
N1 Cd1 2.314(3) 2_755 ?
C5 N2AA 1.369(4) . ?
C5 H5A 0.96(4) . ?
N5 C7 1.319(4) . ?
N5 C9 1.378(4) . ?
C1 N1AA 1.344(4) . ?
C1 H1 0.96(4) . ?
C16 C14 1.410(4) 3_665 ?
C16 C17 1.511(5) . ?
C14 C16 1.410(4) 3_665 ?
O1 H1A 0.83(5) . ?
O1 H1B 0.68(5) . ?
C9 H9 0.9300 . ?
C2 C3 1.348(5) . ?
C2 N1AA 1.378(4) . ?
C2 H2 0.91(3) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
B35 N0AA 1.545(4) . ?
B35 N2AA 1.548(4) . ?
B35 N1AA 1.551(5) . ?

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
N1 Cd1 N7 92.49(9) 2_745 2_645 ?
N1 Cd1 O1 91.61(12) 2_745 . ?
N7 Cd1 O1 81.77(11) 2_645 . ?
N1 Cd1 N3 89.59(9) 2_745 3_766 ?
N7 Cd1 N3 167.94(10) 2_645 3_766 ?
O1 Cd1 N3 86.30(11) . 3_766 ?
N1 Cd1 N5 163.86(10) 2_745 . ?
N7 Cd1 N5 96.34(9) 2_645 . ?
O1 Cd1 N5 103.00(12) . . ?
N3 Cd1 N5 84.60(9) 3_766 . ?
N1 Cd1 O2 82.05(9) 2_745 . ?
N7 Cd1 O2 101.05(8) 2_645 . ?
O1 Cd1 O2 173.13(11) . . ?
N3 Cd1 O2 91.01(9) 3_766 . ?
N5 Cd1 O2 83.01(9) . . ?
C7 N6 C8 104.5(3) . . ?
C7 N6 B35 127.7(3) . . ?
C8 N6 B35 127.7(3) . . ?
N3 C4 N2AA 112.8(3) . . ?
N3 C4 H4 123.4(18) . . ?
N2AA C4 H4 123.7(18) . . ?
C10 N7 C12 105.2(3) . . ?
C10 N7 Cd1 126.3(2) . 2_655 ?
C12 N7 Cd1 128.4(2) . 2_655 ?
C13 O2 Cd1 129.3(2) . . ?
C4 N3 C6 105.1(3) . . ?
C4 N3 Cd1 125.2(2) . 3_766 ?
C6 N3 Cd1 128.9(2) . 3_766 ?
C14 C15 C16 123.8(3) . . ?
C14 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C9 C8 N6 107.7(3) . . ?
C9 C8 H8 126.1 . . ?
N6 C8 H8 126.1 . . ?
N7 C10 N0AA 113.1(3) . . ?
N7 C10 H10 126(2) . . ?
N0AA C10 H10 121(2) . . ?
C17 O5 H5 109.5 . . ?
C11 C12 N7 109.1(3) . . ?
C11 C12 H12 125.4 . . ?
N7 C12 H12 125.4 . . ?
C12 C11 N0AA 107.5(3) . . ?
C12 C11 H11 133(2) . . ?
N0AA C11 H11 120(2) . . ?
O2 C13 O3 123.8(3) . . ?
O2 C13 C14 118.8(3) . . ?
O3 C13 C14 117.2(3) . . ?
C5 C6 N3 109.3(3) . . ?
C5 C6 H6 124.4(17) . . ?
N3 C6 H6 126.3(17) . . ?
C1 N1 C3 105.2(3) . . ?
C1 N1 Cd1 128.3(2) . 2_755 ?
C3 N1 Cd1 125.7(2) . 2_755 ?
C6 C5 N2AA 107.5(3) . . ?
C6 C5 H5A 130(2) . . ?
N2AA C5 H5A 122(2) . . ?
C7 N5 C9 104.0(3) . . ?
C7 N5 Cd1 123.5(2) . . ?
C9 N5 Cd1 129.1(2) . . ?
N1 C1 N1AA 113.1(3) . . ?
N1 C1 H1 128(2) . . ?
N1AA C1 H1 119(2) . . ?
C15 C16 C14 118.0(3) . 3_665 ?
C15 C16 C17 114.4(3) . . ?
C14 C16 C17 127.6(3) 3_665 . ?
C15 C14 C16 118.2(3) . 3_665 ?
C15 C14 C13 115.0(3) . . ?
C16 C14 C13 126.7(3) 3_665 . ?
Cd1 O1 H1A 122(3) . . ?
Cd1 O1 H1B 125(4) . . ?
H1A O1 H1B 103(5) . . ?
C8 C9 N5 110.1(3) . . ?
C8 C9 H9 125.0 . . ?
N5 C9 H9 125.0 . . ?
C3 C2 N1AA 107.9(3) . . ?
C3 C2 H2 130(2) . . ?
N1AA C2 H2 122(2) . . ?
O4 C17 O5 121.1(3) . . ?
O4 C17 C16 119.3(3) . . ?
O5 C17 C16 119.6(3) . . ?
C2 C3 N1 109.1(3) . . ?
C2 C3 H3 125.5 . . ?
N1 C3 H3 125.5 . . ?
N5 C7 N6 113.7(3) . . ?
N5 C7 H7 123.2 . . ?
N6 C7 H7 123.2 . . ?
N6 B35 N0AA 109.9(3) . . ?
N6 B35 N2AA 109.0(3) . . ?
N0AA B35 N2AA 110.5(2) . . ?
N6 B35 N1AA 112.8(2) . . ?
N0AA B35 N1AA 106.5(3) . . ?
N2AA B35 N1AA 108.1(3) . . ?
C1 N1AA C2 104.7(3) . . ?
C1 N1AA B35 130.4(3) . . ?
C2 N1AA B35 124.5(3) . . ?
C4 N2AA C5 105.3(3) . . ?
C4 N2AA B35 127.6(3) . . ?
C5 N2AA B35 127.0(3) . . ?
C10 N0AA C11 105.1(3) . . ?
C10 N0AA B35 125.1(3) . . ?
C11 N0AA B35 129.7(3) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.099

_shelxl_version_number           2014-3

