# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1533275'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 B F2 N2'
_chemical_formula_weight         320.14

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.418(3)
_cell_length_b                   8.632(4)
_cell_length_c                   14.198(6)
_cell_angle_alpha                74.951(6)
_cell_angle_beta                 81.658(7)
_cell_angle_gamma                86.211(7)
_cell_volume                     751.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5270
_cell_measurement_theta_min      6.35
_cell_measurement_theta_max      55.21

_exptl_crystal_description       equiaxed
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6456
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.175
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3403
_reflns_number_gt                2693
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0844P)²+0.1212P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_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
F001 F 0.08980(15) 0.59338(12) 0.56739(7) 0.0365(3) Uani 1 1 d . . . . .
F002 F 0.04315(16) 0.82695(12) 0.61469(7) 0.0382(3) Uani 1 1 d . . . . .
N003 N 0.2917(2) 0.62682(16) 0.68997(9) 0.0287(3) Uani 1 1 d . . . . .
N004 N 0.3635(2) 0.78337(17) 0.51360(9) 0.0295(3) Uani 1 1 d . . . . .
C005 C 0.2253(3) 0.65332(19) 0.78430(11) 0.0296(4) Uani 1 1 d . . . . .
C006 C 0.5570(3) 0.7112(2) 0.50814(11) 0.0289(4) Uani 1 1 d . . . . .
C007 C 0.7107(3) 0.7744(2) 0.42893(11) 0.0330(4) Uani 1 1 d . . . . .
H1 H 0.8465 0.7238 0.4240 0.040 Uiso 1 1 calc R U . . .
C008 C 0.5224(3) 0.3880(2) 0.74844(11) 0.0288(4) Uani 1 1 d . . . . .
C009 C 0.3582(3) 0.2975(2) 0.80832(11) 0.0317(4) Uani 1 1 d . . . . .
H2 H 0.2173 0.3386 0.8074 0.038 Uiso 1 1 calc R U . . .
C00A C 0.5975(3) 0.5738(2) 0.58527(11) 0.0292(4) Uani 1 1 d . . . . .
H3 H 0.7155 0.5053 0.5741 0.035 Uiso 1 1 calc R U . . .
C00B C 0.4742(3) 0.5368(2) 0.67396(11) 0.0279(4) Uani 1 1 d . . . . .
C00C C 0.3709(3) 0.6655(2) 0.84555(12) 0.0328(4) Uani 1 1 d . . . . .
H4 H 0.5173 0.6559 0.8241 0.039 Uiso 1 1 calc R U . . .
C00D C 0.7282(3) 0.3273(2) 0.75316(12) 0.0326(4) Uani 1 1 d . . . . .
H5 H 0.8421 0.3891 0.7145 0.039 Uiso 1 1 calc R U . . .
C00E C 0.0115(3) 0.6691(2) 0.81689(13) 0.0348(4) Uani 1 1 d . . . . .
H6 H -0.0900 0.6602 0.7762 0.042 Uiso 1 1 calc R U . . .
C00F C 0.3991(3) 0.1483(2) 0.86891(12) 0.0370(4) Uani 1 1 d . . . . .
H7 H 0.2863 0.0873 0.9091 0.044 Uiso 1 1 calc R U . . .
C00G C 0.6030(3) 0.0878(2) 0.87121(12) 0.0383(4) Uani 1 1 d . . . . .
H8 H 0.6303 -0.0154 0.9122 0.046 Uiso 1 1 calc R U . . .
C00H C 0.3181(3) 0.9159(2) 0.44290(12) 0.0346(4) Uani 1 1 d . . . . .
H9 H 0.1809 0.9641 0.4475 0.042 Uiso 1 1 calc R U . . .
C00I C 0.6647(3) 0.9093(2) 0.35862(12) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.7689 0.9535 0.3054 0.043 Uiso 1 1 calc R U . . .
C00J C 0.4645(3) 0.9813(2) 0.36557(12) 0.0372(4) Uani 1 1 d . . . . .
H11 H 0.4304 1.0746 0.3171 0.045 Uiso 1 1 calc R U . . .
C00K C 0.3038(3) 0.6913(2) 0.93766(13) 0.0383(4) Uani 1 1 d . . . . .
H12 H 0.4043 0.6968 0.9796 0.046 Uiso 1 1 calc R U . . .
C00L C 0.7680(3) 0.1776(2) 0.81380(13) 0.0373(4) Uani 1 1 d . . . . .
H13 H 0.9087 0.1364 0.8160 0.045 Uiso 1 1 calc R U . . .
C00M C -0.0535(3) 0.6978(2) 0.90829(13) 0.0400(4) Uani 1 1 d . . . . .
H14 H -0.1996 0.7097 0.9297 0.048 Uiso 1 1 calc R U . . .
C00N C 0.0922(3) 0.7091(2) 0.96870(13) 0.0416(5) Uani 1 1 d . . . . .
H15 H 0.0467 0.7291 1.0313 0.050 Uiso 1 1 calc R U . . .
B00O B 0.1860(3) 0.7061(2) 0.60004(14) 0.0307(4) 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
F001 B00O 1.393(2) . ?
F002 B00O 1.380(2) . ?
N003 C00B 1.386(2) . ?
N003 C005 1.417(2) . ?
N003 B00O 1.515(2) . ?
N004 C006 1.353(2) . ?
N004 C00H 1.359(2) . ?
N004 B00O 1.587(2) . ?
C005 C00C 1.391(2) . ?
C005 C00E 1.393(2) . ?
C006 C007 1.402(2) . ?
C006 C00A 1.429(2) . ?
C007 C00I 1.370(2) . ?
C007 H1 0.9500 . ?
C008 C009 1.396(2) . ?
C008 C00D 1.392(2) . ?
C008 C00B 1.484(2) . ?
C009 C00F 1.383(2) . ?
C009 H2 0.9500 . ?
C00A C00B 1.360(2) . ?
C00A H3 0.9500 . ?
C00C C00K 1.386(2) . ?
C00C H4 0.9500 . ?
C00D C00L 1.385(3) . ?
C00D H5 0.9500 . ?
C00E C00M 1.384(2) . ?
C00E H6 0.9500 . ?
C00F C00G 1.378(3) . ?
C00F H7 0.9500 . ?
C00G C00L 1.384(3) . ?
C00G H8 0.9500 . ?
C00H C00J 1.362(2) . ?
C00H H9 0.9500 . ?
C00I C00J 1.392(3) . ?
C00I H10 0.9500 . ?
C00J H11 0.9500 . ?
C00K C00N 1.377(3) . ?
C00K H12 0.9500 . ?
C00L H13 0.9500 . ?
C00M C00N 1.381(3) . ?
C00M H14 0.9500 . ?
C00N H15 0.9500 . ?

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
C00B N003 C005 120.06(14) . . ?
C00B N003 B00O 116.17(13) . . ?
C005 N003 B00O 123.48(14) . . ?
C006 N004 C00H 120.38(15) . . ?
C006 N004 B00O 119.37(14) . . ?
C00H N004 B00O 120.16(15) . . ?
C00C C005 C00E 118.79(15) . . ?
C00C C005 N003 121.05(15) . . ?
C00E C005 N003 120.15(15) . . ?
N004 C006 C007 119.48(16) . . ?
N004 C006 C00A 118.09(14) . . ?
C007 C006 C00A 122.42(16) . . ?
C00I C007 C006 119.82(17) . . ?
C00I C007 H1 120.1 . . ?
C006 C007 H1 120.1 . . ?
C009 C008 C00D 118.74(16) . . ?
C009 C008 C00B 119.78(15) . . ?
C00D C008 C00B 121.15(15) . . ?
C00F C009 C008 120.46(17) . . ?
C00F C009 H2 119.8 . . ?
C008 C009 H2 119.8 . . ?
C00B C00A C006 122.75(16) . . ?
C00B C00A H3 118.6 . . ?
C006 C00A H3 118.6 . . ?
C00A C00B N003 120.08(15) . . ?
C00A C00B C008 119.20(15) . . ?
N003 C00B C008 120.28(14) . . ?
C00K C00C C005 120.49(16) . . ?
C00K C00C H4 119.8 . . ?
C005 C00C H4 119.8 . . ?
C00L C00D C008 120.45(16) . . ?
C00L C00D H5 119.8 . . ?
C008 C00D H5 119.8 . . ?
C00M C00E C005 120.22(17) . . ?
C00M C00E H6 119.9 . . ?
C005 C00E H6 119.9 . . ?
C00G C00F C009 120.28(17) . . ?
C00G C00F H7 119.9 . . ?
C009 C00F H7 119.9 . . ?
C00F C00G C00L 119.93(17) . . ?
C00F C00G H8 120.0 . . ?
C00L C00G H8 120.0 . . ?
N004 C00H C00J 121.62(17) . . ?
N004 C00H H9 119.2 . . ?
C00J C00H H9 119.2 . . ?
C007 C00I C00J 119.71(16) . . ?
C007 C00I H10 120.1 . . ?
C00J C00I H10 120.1 . . ?
C00H C00J C00I 118.99(17) . . ?
C00H C00J H11 120.5 . . ?
C00I C00J H11 120.5 . . ?
C00N C00K C00C 120.31(17) . . ?
C00N C00K H12 119.8 . . ?
C00C C00K H12 119.8 . . ?
C00D C00L C00G 120.10(17) . . ?
C00D C00L H13 119.9 . . ?
C00G C00L H13 119.9 . . ?
C00N C00M C00E 120.55(17) . . ?
C00N C00M H14 119.7 . . ?
C00E C00M H14 119.7 . . ?
C00K C00N C00M 119.62(17) . . ?
C00K C00N H15 120.2 . . ?
C00M C00N H15 120.2 . . ?
F002 B00O F001 110.20(15) . . ?
F002 B00O N003 113.19(14) . . ?
F001 B00O N003 111.14(15) . . ?
F002 B00O N004 107.68(14) . . ?
F001 B00O N004 106.31(13) . . ?
N003 B00O N004 107.99(14) . . ?

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
C00B N003 C005 C00C 32.3(2) . . . . ?
B00O N003 C005 C00C -141.21(17) . . . . ?
C00B N003 C005 C00E -148.32(16) . . . . ?
B00O N003 C005 C00E 38.2(2) . . . . ?
C00H N004 C006 C007 0.1(2) . . . . ?
B00O N004 C006 C007 176.62(14) . . . . ?
C00H N004 C006 C00A 178.99(14) . . . . ?
B00O N004 C006 C00A -4.5(2) . . . . ?
N004 C006 C007 C00I 0.8(2) . . . . ?
C00A C006 C007 C00I -178.06(15) . . . . ?
C00D C008 C009 C00F -1.9(2) . . . . ?
C00B C008 C009 C00F 171.54(15) . . . . ?
N004 C006 C00A C00B -17.0(2) . . . . ?
C007 C006 C00A C00B 161.82(16) . . . . ?
C006 C00A C00B N003 5.1(2) . . . . ?
C006 C00A C00B C008 177.40(14) . . . . ?
C005 N003 C00B C00A -146.00(15) . . . . ?
B00O N003 C00B C00A 27.9(2) . . . . ?
C005 N003 C00B C008 41.7(2) . . . . ?
B00O N003 C00B C008 -144.32(15) . . . . ?
C009 C008 C00B C00A -142.51(16) . . . . ?
C00D C008 C00B C00A 30.8(2) . . . . ?
C009 C008 C00B N003 29.8(2) . . . . ?
C00D C008 C00B N003 -156.88(15) . . . . ?
C00E C005 C00C C00K 0.6(3) . . . . ?
N003 C005 C00C C00K -179.98(15) . . . . ?
C009 C008 C00D C00L 2.1(2) . . . . ?
C00B C008 C00D C00L -171.23(15) . . . . ?
C00C C005 C00E C00M 0.6(3) . . . . ?
N003 C005 C00E C00M -178.88(15) . . . . ?
C008 C009 C00F C00G 0.4(3) . . . . ?
C009 C00F C00G C00L 1.0(3) . . . . ?
C006 N004 C00H C00J -0.8(2) . . . . ?
B00O N004 C00H C00J -177.29(15) . . . . ?
C006 C007 C00I C00J -1.0(3) . . . . ?
N004 C00H C00J C00I 0.6(3) . . . . ?
C007 C00I C00J C00H 0.3(3) . . . . ?
C005 C00C C00K C00N -1.5(3) . . . . ?
C008 C00D C00L C00G -0.8(3) . . . . ?
C00F C00G C00L C00D -0.8(3) . . . . ?
C005 C00E C00M C00N -0.8(3) . . . . ?
C00C C00K C00N C00M 1.3(3) . . . . ?
C00E C00M C00N C00K -0.2(3) . . . . ?
C00B N003 B00O F002 -163.14(13) . . . . ?
C005 N003 B00O F002 10.6(2) . . . . ?
C00B N003 B00O F001 72.22(18) . . . . ?
C005 N003 B00O F001 -114.08(17) . . . . ?
C00B N003 B00O N004 -44.03(19) . . . . ?
C005 N003 B00O N004 129.68(15) . . . . ?
C006 N004 B00O F002 155.48(14) . . . . ?
C00H N004 B00O F002 -28.0(2) . . . . ?
C006 N004 B00O F001 -86.42(17) . . . . ?
C00H N004 B00O F001 90.11(18) . . . . ?
C006 N004 B00O N003 32.9(2) . . . . ?
C00H N004 B00O N003 -150.54(14) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1533277'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 B F2 N2'
_chemical_formula_weight         318.12

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.2376(8)
_cell_length_b                   11.5433(11)
_cell_length_c                   13.4497(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.264(7)
_cell_angle_gamma                90
_cell_volume                     1419.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      6.12
_cell_measurement_theta_max      55.10

_exptl_crystal_description       equiaxed
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13004
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3230
_reflns_number_gt                2658
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1037P)²+0.2460P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_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
F001 F 0.90716(10) 0.34415(8) 0.58320(7) 0.0303(3) Uani 1 1 d . . . . .
F002 F 0.81717(11) 0.45588(8) 0.44940(7) 0.0308(3) Uani 1 1 d . . . . .
N003 N 0.74304(15) 0.49605(12) 0.60852(10) 0.0249(3) Uani 1 1 d . . . . .
N004 N 0.65531(14) 0.31375(12) 0.50848(10) 0.0243(3) Uani 1 1 d . . . . .
C005 C 0.52571(17) 0.32498(14) 0.54696(11) 0.0243(4) Uani 1 1 d . . . . .
C006 C 0.50574(18) 0.41531(14) 0.61046(12) 0.0266(4) Uani 1 1 d . . . . .
H1 H 0.4142 0.4206 0.6346 0.032 Uiso 1 1 calc R U . . .
C007 C 0.61174(18) 0.50045(14) 0.64211(12) 0.0256(4) Uani 1 1 d . . . . .
C008 C 0.67518(18) 0.22477(14) 0.43944(12) 0.0255(4) Uani 1 1 d . . . . .
C009 C 0.40942(18) 0.23943(14) 0.51998(12) 0.0260(4) Uani 1 1 d . . . . .
C00A C 0.56232(19) 0.14565(14) 0.40766(12) 0.0268(4) Uani 1 1 d . . . . .
C00B C 0.27789(19) 0.24492(16) 0.56132(13) 0.0307(4) Uani 1 1 d . . . . .
H2 H 0.2649 0.3047 0.6077 0.037 Uiso 1 1 calc R U . . .
C00C C 0.80769(19) 0.21473(15) 0.40099(13) 0.0295(4) Uani 1 1 d . . . . .
H3 H 0.8858 0.2661 0.4236 0.035 Uiso 1 1 calc R U . . .
C00D C 0.84846(19) 0.57672(15) 0.63806(13) 0.0294(4) Uani 1 1 d . . . . .
H4 H 0.9393 0.5719 0.6130 0.035 Uiso 1 1 calc R U . . .
C00E C 0.42717(19) 0.15092(14) 0.45112(12) 0.0271(4) Uani 1 1 d . . . . .
C00F C 0.5858(2) 0.59133(15) 0.70797(12) 0.0311(4) Uani 1 1 d . . . . .
H5 H 0.4939 0.5963 0.7316 0.037 Uiso 1 1 calc R U . . .
C00G C 0.31259(19) 0.07061(15) 0.42597(13) 0.0318(4) Uani 1 1 d . . . . .
H6 H 0.3235 0.0107 0.3792 0.038 Uiso 1 1 calc R U . . .
C00H C 0.5843(2) 0.06287(16) 0.33502(13) 0.0330(4) Uani 1 1 d . . . . .
H7 H 0.5076 0.0103 0.3121 0.040 Uiso 1 1 calc R U . . .
C00I C 0.1677(2) 0.16539(16) 0.53587(14) 0.0337(4) Uani 1 1 d . . . . .
H8 H 0.0797 0.1703 0.5645 0.040 Uiso 1 1 calc R U . . .
C00J C 0.6906(2) 0.67134(15) 0.73777(13) 0.0339(4) Uani 1 1 d . . . . .
H9 H 0.6724 0.7319 0.7821 0.041 Uiso 1 1 calc R U . . .
C00K C 0.8262(2) 0.13095(16) 0.33054(13) 0.0333(4) Uani 1 1 d . . . . .
H10 H 0.9171 0.1251 0.3057 0.040 Uiso 1 1 calc R U . . .
C00L C 0.7139(2) 0.05547(16) 0.29582(13) 0.0356(4) Uani 1 1 d . . . . .
H11 H 0.7259 -0.0005 0.2458 0.043 Uiso 1 1 calc R U . . .
C00M C 0.1865(2) 0.07716(16) 0.46745(14) 0.0352(4) Uani 1 1 d . . . . .
H12 H 0.1112 0.0217 0.4499 0.042 Uiso 1 1 calc R U . . .
C00N C 0.8269(2) 0.66403(15) 0.70254(13) 0.0333(4) Uani 1 1 d . . . . .
H13 H 0.9020 0.7187 0.7233 0.040 Uiso 1 1 calc R U . . .
B00O B 0.7837(2) 0.40050(16) 0.53537(13) 0.0250(4) 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
F001 B00O 1.388(2) . ?
F002 B00O 1.394(2) . ?
N003 C007 1.355(2) . ?
N003 C00D 1.365(2) . ?
N003 B00O 1.559(2) . ?
N004 C005 1.377(2) . ?
N004 C008 1.414(2) . ?
N004 B00O 1.554(2) . ?
C005 C006 1.377(2) . ?
C005 C009 1.466(2) . ?
C006 C007 1.409(2) . ?
C006 H1 0.9500 . ?
C007 C00F 1.415(2) . ?
C008 C00C 1.400(2) . ?
C008 C00A 1.406(2) . ?
C009 C00E 1.404(2) . ?
C009 C00B 1.408(2) . ?
C00A C00H 1.402(2) . ?
C00A C00E 1.454(2) . ?
C00B C00I 1.377(3) . ?
C00B H2 0.9500 . ?
C00C C00K 1.382(2) . ?
C00C H3 0.9500 . ?
C00D C00N 1.363(2) . ?
C00D H4 0.9500 . ?
C00E C00G 1.411(2) . ?
C00F C00J 1.356(3) . ?
C00F H5 0.9500 . ?
C00G C00M 1.364(3) . ?
C00G H6 0.9500 . ?
C00H C00L 1.378(3) . ?
C00H H7 0.9500 . ?
C00I C00M 1.400(3) . ?
C00I H8 0.9500 . ?
C00J C00N 1.410(3) . ?
C00J H9 0.9500 . ?
C00K C00L 1.383(3) . ?
C00K H10 0.9500 . ?
C00L H11 0.9500 . ?
C00M H12 0.9500 . ?
C00N H13 0.9500 . ?

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
C007 N003 C00D 120.86(14) . . ?
C007 N003 B00O 123.03(14) . . ?
C00D N003 B00O 116.11(13) . . ?
C005 N004 C008 121.14(14) . . ?
C005 N004 B00O 121.81(13) . . ?
C008 N004 B00O 117.01(13) . . ?
C006 C005 N004 120.37(15) . . ?
C006 C005 C009 120.33(15) . . ?
N004 C005 C009 119.30(14) . . ?
C005 C006 C007 124.49(15) . . ?
C005 C006 H1 117.8 . . ?
C007 C006 H1 117.8 . . ?
N003 C007 C006 119.31(15) . . ?
N003 C007 C00F 118.46(15) . . ?
C006 C007 C00F 122.23(15) . . ?
C00C C008 C00A 118.91(15) . . ?
C00C C008 N004 120.36(15) . . ?
C00A C008 N004 120.73(15) . . ?
C00E C009 C00B 118.82(16) . . ?
C00E C009 C005 120.17(15) . . ?
C00B C009 C005 121.00(15) . . ?
C00H C00A C008 118.63(16) . . ?
C00H C00A C00E 121.84(16) . . ?
C008 C00A C00E 119.52(15) . . ?
C00I C00B C009 121.38(16) . . ?
C00I C00B H2 119.3 . . ?
C009 C00B H2 119.3 . . ?
C00K C00C C008 120.80(16) . . ?
C00K C00C H3 119.6 . . ?
C008 C00C H3 119.6 . . ?
C00N C00D N003 121.77(16) . . ?
C00N C00D H4 119.1 . . ?
N003 C00D H4 119.1 . . ?
C009 C00E C00G 118.78(16) . . ?
C009 C00E C00A 118.95(15) . . ?
C00G C00E C00A 122.27(15) . . ?
C00J C00F C007 120.79(17) . . ?
C00J C00F H5 119.6 . . ?
C007 C00F H5 119.6 . . ?
C00M C00G C00E 121.38(17) . . ?
C00M C00G H6 119.3 . . ?
C00E C00G H6 119.3 . . ?
C00L C00H C00A 121.99(17) . . ?
C00L C00H H7 119.0 . . ?
C00A C00H H7 119.0 . . ?
C00B C00I C00M 119.45(16) . . ?
C00B C00I H8 120.3 . . ?
C00M C00I H8 120.3 . . ?
C00F C00J C00N 119.59(16) . . ?
C00F C00J H9 120.2 . . ?
C00N C00J H9 120.2 . . ?
C00C C00K C00L 120.77(16) . . ?
C00C C00K H10 119.6 . . ?
C00L C00K H10 119.6 . . ?
C00H C00L C00K 118.82(16) . . ?
C00H C00L H11 120.6 . . ?
C00K C00L H11 120.6 . . ?
C00G C00M C00I 120.19(17) . . ?
C00G C00M H12 119.9 . . ?
C00I C00M H12 119.9 . . ?
C00D C00N C00J 118.52(16) . . ?
C00D C00N H13 120.7 . . ?
C00J C00N H13 120.7 . . ?
F001 B00O F002 109.47(14) . . ?
F001 B00O N004 110.76(14) . . ?
F002 B00O N004 110.81(13) . . ?
F001 B00O N003 107.18(13) . . ?
F002 B00O N003 107.53(13) . . ?
N004 B00O N003 110.97(13) . . ?

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
C008 N004 C005 C006 -176.96(14) . . . . ?
B00O N004 C005 C006 0.6(2) . . . . ?
C008 N004 C005 C009 3.3(2) . . . . ?
B00O N004 C005 C009 -179.11(13) . . . . ?
N004 C005 C006 C007 -0.9(3) . . . . ?
C009 C005 C006 C007 178.82(14) . . . . ?
C00D N003 C007 C006 -179.65(14) . . . . ?
B00O N003 C007 C006 0.2(2) . . . . ?
C00D N003 C007 C00F 0.5(2) . . . . ?
B00O N003 C007 C00F -179.66(14) . . . . ?
C005 C006 C007 N003 0.5(2) . . . . ?
C005 C006 C007 C00F -179.68(15) . . . . ?
C005 N004 C008 C00C 179.93(14) . . . . ?
B00O N004 C008 C00C 2.3(2) . . . . ?
C005 N004 C008 C00A 0.4(2) . . . . ?
B00O N004 C008 C00A -177.24(14) . . . . ?
C006 C005 C009 C00E 176.67(15) . . . . ?
N004 C005 C009 C00E -3.6(2) . . . . ?
C006 C005 C009 C00B -2.6(2) . . . . ?
N004 C005 C009 C00B 177.11(14) . . . . ?
C00C C008 C00A C00H -2.9(2) . . . . ?
N004 C008 C00A C00H 176.58(15) . . . . ?
C00C C008 C00A C00E 176.57(15) . . . . ?
N004 C008 C00A C00E -3.9(2) . . . . ?
C00E C009 C00B C00I 0.3(3) . . . . ?
C005 C009 C00B C00I 179.56(16) . . . . ?
C00A C008 C00C C00K 2.1(3) . . . . ?
N004 C008 C00C C00K -177.45(15) . . . . ?
C007 N003 C00D C00N 0.4(2) . . . . ?
B00O N003 C00D C00N -179.40(15) . . . . ?
C00B C009 C00E C00G -0.1(2) . . . . ?
C005 C009 C00E C00G -179.38(14) . . . . ?
C00B C009 C00E C00A 179.47(14) . . . . ?
C005 C009 C00E C00A 0.2(2) . . . . ?
C00H C00A C00E C009 -176.98(15) . . . . ?
C008 C00A C00E C009 3.5(2) . . . . ?
C00H C00A C00E C00G 2.5(3) . . . . ?
C008 C00A C00E C00G -176.93(15) . . . . ?
N003 C007 C00F C00J -0.8(2) . . . . ?
C006 C007 C00F C00J 179.38(15) . . . . ?
C009 C00E C00G C00M -0.4(3) . . . . ?
C00A C00E C00G C00M -179.88(16) . . . . ?
C008 C00A C00H C00L 1.4(3) . . . . ?
C00E C00A C00H C00L -178.07(16) . . . . ?
C009 C00B C00I C00M 0.0(3) . . . . ?
C007 C00F C00J C00N 0.1(3) . . . . ?
C008 C00C C00K C00L 0.4(3) . . . . ?
C00A C00H C00L C00K 1.1(3) . . . . ?
C00C C00K C00L C00H -2.0(3) . . . . ?
C00E C00G C00M C00I 0.6(3) . . . . ?
C00B C00I C00M C00G -0.4(3) . . . . ?
N003 C00D C00N C00J -1.1(3) . . . . ?
C00F C00J C00N C00D 0.8(3) . . . . ?
C005 N004 B00O F001 118.90(15) . . . . ?
C008 N004 B00O F001 -63.43(17) . . . . ?
C005 N004 B00O F002 -119.40(15) . . . . ?
C008 N004 B00O F002 58.26(18) . . . . ?
C005 N004 B00O N003 0.0(2) . . . . ?
C008 N004 B00O N003 177.65(13) . . . . ?
C007 N003 B00O F001 -121.42(15) . . . . ?
C00D N003 B00O F001 58.39(17) . . . . ?
C007 N003 B00O F002 120.96(15) . . . . ?
C00D N003 B00O F002 -59.22(18) . . . . ?
C007 N003 B00O N004 -0.4(2) . . . . ?
C00D N003 B00O N004 179.45(13) . . . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.102



