# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ProfFuruta
_database_code_depnum_ccdc_archive 'CCDC 1055488'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 B Cl2 F2 N3'
_chemical_formula_sum            'C19 H18 B Cl2 F2 N3'
_chemical_formula_weight         408.07

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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   25.408(9)
_cell_length_b                   8.297(3)
_cell_length_c                   8.766(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1848.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7458
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      31.29

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.380
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            30147
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4460
_reflns_number_gt                4322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'
_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)+(0.0369P)²+0.3305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1898 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4460
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Cl1 Cl -0.00651(2) 0.84700(7) -0.30614(7) 0.02423(12) Uani 1 1 d . . . . .
Cl2 Cl 0.02029(2) 0.62370(7) 0.30922(7) 0.02509(13) Uani 1 1 d . . . . .
F1 F 0.37798(6) 1.45296(17) 0.09165(18) 0.0318(3) Uani 1 1 d . . . . .
F2 F 0.39401(5) 1.32000(17) 0.31334(17) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.36168(7) 1.1672(2) 0.0999(2) 0.0168(4) Uani 1 1 d . . . . .
N2 N 0.30370(7) 1.3563(2) 0.2372(2) 0.0162(4) Uani 1 1 d . . . . .
N3 N 0.09308(7) 0.6953(2) 0.0225(2) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.40284(8) 1.1036(3) 0.0246(3) 0.0223(5) Uani 1 1 d . . . . .
H1 H 0.4372 1.1491 0.0224 0.027 Uiso 1 1 calc R U . . .
C2 C 0.38823(9) 0.9615(3) -0.0499(3) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.4103 0.8944 -0.1102 0.027 Uiso 1 1 calc R U . . .
C3 C 0.33536(8) 0.9376(3) -0.0186(2) 0.0177(4) Uani 1 1 d . . . . .
H3 H 0.3142 0.8510 -0.0544 0.021 Uiso 1 1 calc R U . . .
C4 C 0.31856(8) 1.0657(3) 0.0762(2) 0.0149(4) Uani 1 1 d . . . . .
C5 C 0.26855(8) 1.1073(2) 0.1311(2) 0.0137(4) Uani 1 1 d . . . . .
C6 C 0.26169(8) 1.2519(2) 0.2138(2) 0.0144(4) Uani 1 1 d . . . . .
C7 C 0.21752(8) 1.3127(2) 0.2935(3) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.1835 1.2652 0.2982 0.021 Uiso 1 1 calc R U . . .
C8 C 0.23324(9) 1.4553(3) 0.3640(3) 0.0212(5) Uani 1 1 d . . . . .
H8 H 0.2121 1.5238 0.4254 0.025 Uiso 1 1 calc R U . . .
C9 C 0.28638(9) 1.4781(2) 0.3266(3) 0.0204(4) Uani 1 1 d . . . . .
H9 H 0.3073 1.5665 0.3593 0.024 Uiso 1 1 calc R U . . .
C10 C 0.22318(8) 1.0017(2) 0.1029(2) 0.0141(4) Uani 1 1 d . . . . .
C11 C 0.17633(8) 1.0616(3) 0.0400(2) 0.0158(4) Uani 1 1 d . . . . .
H11 H 0.1737 1.1731 0.0168 0.019 Uiso 1 1 calc R U . . .
C12 C 0.13382(8) 0.9622(2) 0.0108(2) 0.0157(4) Uani 1 1 d . . . . .
H12 H 0.1031 1.0058 -0.0355 0.019 Uiso 1 1 calc R U . . .
C13 C 0.13540(8) 0.7965(2) 0.0489(2) 0.0144(4) Uani 1 1 d . . . . .
C14 C 0.18250(7) 0.7376(2) 0.1138(2) 0.0142(4) Uani 1 1 d . . . . .
H14 H 0.1847 0.6273 0.1420 0.017 Uiso 1 1 calc R U . . .
C15 C 0.22555(8) 0.8369(2) 0.1371(2) 0.0148(4) Uani 1 1 d . . . . .
H15 H 0.2572 0.7926 0.1770 0.018 Uiso 1 1 calc R U . . .
C16 C 0.04531(8) 0.7553(3) -0.0507(2) 0.0171(4) Uani 1 1 d . . . . .
H16A H 0.0371 0.8643 -0.0116 0.021 Uiso 1 1 calc R U . . .
H16B H 0.0154 0.6835 -0.0254 0.021 Uiso 1 1 calc R U . . .
C17 C 0.05230(8) 0.7622(3) -0.2236(2) 0.0192(4) Uani 1 1 d . . . . .
H17A H 0.0583 0.6525 -0.2644 0.023 Uiso 1 1 calc R U . . .
H17B H 0.0831 0.8298 -0.2496 0.023 Uiso 1 1 calc R U . . .
C18 C 0.09131(8) 0.5338(2) 0.0903(3) 0.0168(4) Uani 1 1 d . . . . .
H18A H 0.1248 0.4777 0.0677 0.020 Uiso 1 1 calc R U . . .
H18B H 0.0626 0.4718 0.0415 0.020 Uiso 1 1 calc R U . . .
C19 C 0.08273(8) 0.5341(3) 0.2613(3) 0.0190(4) Uani 1 1 d . . . . .
H19A H 0.1114 0.5953 0.3113 0.023 Uiso 1 1 calc R U . . .
H19B H 0.0838 0.4220 0.2999 0.023 Uiso 1 1 calc R U . . .
B1 B 0.36137(9) 1.3290(3) 0.1869(3) 0.0191(5) 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
Cl1 C17 1.803(2) . ?
Cl2 C19 1.802(2) . ?
F1 B1 1.391(3) . ?
F2 B1 1.386(3) . ?
N1 C1 1.344(3) . ?
N1 C4 1.398(3) . ?
N1 B1 1.544(3) . ?
N2 C9 1.352(3) . ?
N2 C6 1.390(3) . ?
N2 B1 1.547(3) . ?
N3 C13 1.384(3) . ?
N3 C16 1.460(3) . ?
N3 C18 1.466(3) . ?
C1 C2 1.399(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.415(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(3) . ?
C5 C6 1.412(3) . ?
C5 C10 1.469(3) . ?
C6 C7 1.415(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.402(3) . ?
C10 C11 1.403(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.412(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.527(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.515(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
C1 N1 C4 107.47(18) . . ?
C1 N1 B1 126.00(18) . . ?
C4 N1 B1 126.41(17) . . ?
C9 N2 C6 107.55(18) . . ?
C9 N2 B1 125.63(18) . . ?
C6 N2 B1 126.46(17) . . ?
C13 N3 C16 120.85(17) . . ?
C13 N3 C18 120.70(17) . . ?
C16 N3 C18 117.62(16) . . ?
N1 C1 C2 110.73(19) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C3 C2 C1 106.6(2) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.5(2) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C5 120.73(19) . . ?
N1 C4 C3 107.68(18) . . ?
C5 C4 C3 131.3(2) . . ?
C4 C5 C6 119.81(18) . . ?
C4 C5 C10 120.44(18) . . ?
C6 C5 C10 119.75(17) . . ?
N2 C6 C5 120.69(18) . . ?
N2 C6 C7 108.30(17) . . ?
C5 C6 C7 130.85(18) . . ?
C8 C7 C6 107.11(19) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 106.68(19) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 110.36(19) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C15 C10 C11 117.77(18) . . ?
C15 C10 C5 120.79(18) . . ?
C11 C10 C5 121.43(18) . . ?
C12 C11 C10 121.67(19) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.86(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
N3 C13 C14 121.07(18) . . ?
N3 C13 C12 121.85(19) . . ?
C14 C13 C12 117.08(18) . . ?
C15 C14 C13 121.56(18) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 120.99(18) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
N3 C16 C17 110.63(16) . . ?
N3 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 Cl1 108.46(14) . . ?
C16 C17 H17A 110.0 . . ?
Cl1 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
Cl1 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
N3 C18 C19 113.81(19) . . ?
N3 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 Cl2 110.97(16) . . ?
C18 C19 H19A 109.4 . . ?
Cl2 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
Cl2 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
F2 B1 F1 109.78(17) . . ?
F2 B1 N1 110.19(19) . . ?
F1 B1 N1 110.16(19) . . ?
F2 B1 N2 110.31(19) . . ?
F1 B1 N2 110.51(18) . . ?
N1 B1 N2 105.83(16) . . ?

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
C4 N1 C1 C2 0.3(3) . . . . ?
B1 N1 C1 C2 -175.8(2) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 N1 C4 C5 -174.9(2) . . . . ?
B1 N1 C4 C5 1.1(3) . . . . ?
C1 N1 C4 C3 -0.6(2) . . . . ?
B1 N1 C4 C3 175.51(19) . . . . ?
C2 C3 C4 N1 0.7(2) . . . . ?
C2 C3 C4 C5 174.2(2) . . . . ?
N1 C4 C5 C6 -1.2(3) . . . . ?
C3 C4 C5 C6 -174.1(2) . . . . ?
N1 C4 C5 C10 178.62(18) . . . . ?
C3 C4 C5 C10 5.8(3) . . . . ?
C9 N2 C6 C5 -176.44(19) . . . . ?
B1 N2 C6 C5 -3.1(3) . . . . ?
C9 N2 C6 C7 -0.6(2) . . . . ?
B1 N2 C6 C7 172.80(19) . . . . ?
C4 C5 C6 N2 2.1(3) . . . . ?
C10 C5 C6 N2 -177.69(18) . . . . ?
C4 C5 C6 C7 -172.7(2) . . . . ?
C10 C5 C6 C7 7.5(3) . . . . ?
N2 C6 C7 C8 0.5(2) . . . . ?
C5 C6 C7 C8 175.8(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C6 N2 C9 C8 0.4(2) . . . . ?
B1 N2 C9 C8 -173.0(2) . . . . ?
C7 C8 C9 N2 -0.1(2) . . . . ?
C4 C5 C10 C15 51.1(3) . . . . ?
C6 C5 C10 C15 -129.1(2) . . . . ?
C4 C5 C10 C11 -128.4(2) . . . . ?
C6 C5 C10 C11 51.4(3) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C5 C10 C11 C12 178.9(2) . . . . ?
C10 C11 C12 C13 2.4(3) . . . . ?
C16 N3 C13 C14 -177.29(18) . . . . ?
C18 N3 C13 C14 13.3(3) . . . . ?
C16 N3 C13 C12 1.9(3) . . . . ?
C18 N3 C13 C12 -167.46(19) . . . . ?
C11 C12 C13 N3 179.2(2) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
N3 C13 C14 C15 178.4(2) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C10 2.7(3) . . . . ?
C11 C10 C15 C14 -1.9(3) . . . . ?
C5 C10 C15 C14 178.58(19) . . . . ?
C13 N3 C16 C17 80.8(2) . . . . ?
C18 N3 C16 C17 -109.5(2) . . . . ?
N3 C16 C17 Cl1 -176.96(13) . . . . ?
C13 N3 C18 C19 70.7(3) . . . . ?
C16 N3 C18 C19 -99.1(2) . . . . ?
N3 C18 C19 Cl2 62.0(2) . . . . ?
C1 N1 B1 F2 -67.0(3) . . . . ?
C4 N1 B1 F2 117.6(2) . . . . ?
C1 N1 B1 F1 54.3(3) . . . . ?
C4 N1 B1 F1 -121.1(2) . . . . ?
C1 N1 B1 N2 173.8(2) . . . . ?
C4 N1 B1 N2 -1.6(3) . . . . ?
C9 N2 B1 F2 55.6(3) . . . . ?
C6 N2 B1 F2 -116.6(2) . . . . ?
C9 N2 B1 F1 -66.0(3) . . . . ?
C6 N2 B1 F1 121.8(2) . . . . ?
C9 N2 B1 N1 174.79(19) . . . . ?
C6 N2 B1 N1 2.6(3) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_ProfFuruta
_database_code_depnum_ccdc_archive 'CCDC 1058841'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 B F2 N9'
_chemical_formula_sum            'C19 H18 B F2 N9'
_chemical_formula_weight         421.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   12.295(6)
_cell_length_b                   20.765(10)
_cell_length_c                   7.858(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.122(9)
_cell_angle_gamma                90
_cell_volume                     1975.1(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6007
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      31.30

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            33795
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.948
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4782
_reflns_number_gt                4058
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'
_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)+(0.0719P)²+0.5304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4782
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
F1 F 1.15457(9) 0.09404(5) 1.18012(14) 0.0267(3) Uani 1 1 d . . . . .
F2 F 1.25176(9) 0.09952(5) 0.96118(15) 0.0262(3) Uani 1 1 d . . . . .
N1 N 1.05329(12) 0.11233(7) 0.8925(2) 0.0214(3) Uani 1 1 d . . . . .
N2 N 1.17063(12) 0.19787(7) 1.04716(19) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.63948(11) 0.40084(7) 0.65821(18) 0.0173(3) Uani 1 1 d . . . . .
N4 N 0.40526(13) 0.38473(7) 0.9006(2) 0.0253(3) Uani 1 1 d . . . . .
N5 N 0.35220(12) 0.42420(7) 0.96772(19) 0.0226(3) Uani 1 1 d . . . . .
N6 N 0.29487(14) 0.45632(8) 1.0290(2) 0.0327(4) Uani 1 1 d . . . . .
N7 N 0.56167(13) 0.43651(7) 0.28965(19) 0.0242(3) Uani 1 1 d . . . . .
N8 N 0.54551(13) 0.37772(8) 0.2967(2) 0.0250(3) Uani 1 1 d . . . . .
N9 N 0.52037(15) 0.32499(9) 0.2888(2) 0.0354(4) Uani 1 1 d . . . . .
C1 C 1.01919(16) 0.05598(9) 0.8145(3) 0.0272(4) Uani 1 1 d . . . . .
H1 H 1.0573 0.0162 0.8356 0.033 Uiso 1 1 calc R U . . .
C2 C 0.92067(16) 0.06431(9) 0.6993(3) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.8805 0.0321 0.6286 0.032 Uiso 1 1 calc R U . . .
C3 C 0.89233(14) 0.12904(8) 0.7075(2) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.8291 0.1494 0.6429 0.026 Uiso 1 1 calc R U . . .
C4 C 0.97505(13) 0.15880(8) 0.8297(2) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.99079(13) 0.22411(8) 0.8785(2) 0.0171(3) Uani 1 1 d . . . . .
C6 C 1.09027(13) 0.24321(8) 0.9819(2) 0.0178(3) Uani 1 1 d . . . . .
C7 C 1.12896(14) 0.30447(8) 1.0468(2) 0.0192(3) Uani 1 1 d . . . . .
H7 H 1.0911 0.3443 1.0250 0.023 Uiso 1 1 calc R U . . .
C8 C 1.23181(14) 0.29535(9) 1.1476(2) 0.0215(4) Uani 1 1 d . . . . .
H8 H 1.2785 0.3277 1.2065 0.026 Uiso 1 1 calc R U . . .
C9 C 1.25409(14) 0.22930(9) 1.1463(2) 0.0220(4) Uani 1 1 d . . . . .
H9 H 1.3191 0.2095 1.2069 0.026 Uiso 1 1 calc R U . . .
C10 C 0.90131(13) 0.27035(8) 0.8222(2) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.79242(14) 0.25586(8) 0.8394(2) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.7770 0.2154 0.8865 0.022 Uiso 1 1 calc R U . . .
C12 C 0.70690(14) 0.29884(8) 0.7896(2) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.6345 0.2880 0.8065 0.022 Uiso 1 1 calc R U . . .
C13 C 0.72529(13) 0.35847(8) 0.7140(2) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.83505(13) 0.37284(8) 0.6965(2) 0.0169(3) Uani 1 1 d . . . . .
H14 H 0.8505 0.4126 0.6457 0.020 Uiso 1 1 calc R U . . .
C15 C 0.92055(13) 0.33037(8) 0.7517(2) 0.0170(3) Uani 1 1 d . . . . .
H15 H 0.9938 0.3421 0.7415 0.020 Uiso 1 1 calc R U . . .
C16 C 0.52789(13) 0.38764(8) 0.6885(2) 0.0186(3) Uani 1 1 d . . . . .
H16A H 0.5116 0.3412 0.6705 0.022 Uiso 1 1 calc R U . . .
H16B H 0.4740 0.4121 0.6043 0.022 Uiso 1 1 calc R U . . .
C17 C 0.51541(14) 0.40637(8) 0.8707(2) 0.0211(4) Uani 1 1 d . . . . .
H17A H 0.5742 0.3858 0.9555 0.025 Uiso 1 1 calc R U . . .
H17B H 0.5221 0.4536 0.8851 0.025 Uiso 1 1 calc R U . . .
C18 C 0.65977(14) 0.46354(8) 0.5859(2) 0.0183(3) Uani 1 1 d . . . . .
H18A H 0.7297 0.4814 0.6502 0.022 Uiso 1 1 calc R U . . .
H18B H 0.5994 0.4934 0.6009 0.022 Uiso 1 1 calc R U . . .
C19 C 0.66705(15) 0.45948(8) 0.3949(2) 0.0216(4) Uani 1 1 d . . . . .
H19A H 0.6851 0.5025 0.3534 0.026 Uiso 1 1 calc R U . . .
H19B H 0.7274 0.4297 0.3796 0.026 Uiso 1 1 calc R U . . .
B1 B 1.16068(17) 0.12377(10) 1.0235(3) 0.0218(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
F1 B1 1.391(2) . ?
F2 B1 1.393(2) . ?
N1 C1 1.353(2) . ?
N1 C4 1.390(2) . ?
N1 B1 1.543(3) . ?
N2 C9 1.343(2) . ?
N2 C6 1.396(2) . ?
N2 B1 1.552(3) . ?
N3 C13 1.384(2) . ?
N3 C16 1.459(2) . ?
N3 C18 1.460(2) . ?
N4 N5 1.223(2) . ?
N4 C17 1.484(2) . ?
N5 N6 1.137(2) . ?
N7 N8 1.240(2) . ?
N7 C19 1.488(2) . ?
N8 N9 1.137(2) . ?
C1 C2 1.390(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(2) . ?
C5 C6 1.401(2) . ?
C5 C10 1.469(2) . ?
C6 C7 1.421(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.401(2) . ?
C10 C11 1.402(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.412(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.518(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
C1 N1 C4 107.42(15) . . ?
C1 N1 B1 126.59(15) . . ?
C4 N1 B1 125.97(14) . . ?
C9 N2 C6 107.74(14) . . ?
C9 N2 B1 125.96(15) . . ?
C6 N2 B1 126.08(15) . . ?
C13 N3 C16 121.00(14) . . ?
C13 N3 C18 121.16(13) . . ?
C16 N3 C18 117.45(13) . . ?
N5 N4 C17 115.85(15) . . ?
N6 N5 N4 173.14(18) . . ?
N8 N7 C19 114.93(15) . . ?
N9 N8 N7 172.12(19) . . ?
N1 C1 C2 110.66(16) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C1 C2 C3 106.63(16) . . ?
C1 C2 H2 126.7 . . ?
C3 C2 H2 126.7 . . ?
C2 C3 C4 107.32(16) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.95(15) . . ?
N1 C4 C5 121.09(15) . . ?
C3 C4 C5 130.71(15) . . ?
C6 C5 C4 119.52(15) . . ?
C6 C5 C10 121.39(15) . . ?
C4 C5 C10 119.07(15) . . ?
N2 C6 C5 120.77(15) . . ?
N2 C6 C7 107.53(15) . . ?
C5 C6 C7 131.64(15) . . ?
C8 C7 C6 107.34(15) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.89(16) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
N2 C9 C8 110.50(15) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C15 C10 C11 117.36(15) . . ?
C15 C10 C5 122.09(15) . . ?
C11 C10 C5 120.54(15) . . ?
C12 C11 C10 121.74(15) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.09(15) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N3 C13 C12 121.49(14) . . ?
N3 C13 C14 121.53(15) . . ?
C12 C13 C14 116.98(14) . . ?
C15 C14 C13 121.46(15) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 121.30(15) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
N3 C16 C17 111.08(14) . . ?
N3 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N4 C17 C16 108.56(14) . . ?
N4 C17 H17A 110.0 . . ?
C16 C17 H17A 110.0 . . ?
N4 C17 H17B 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
N3 C18 C19 112.25(14) . . ?
N3 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N3 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
N7 C19 C18 111.69(14) . . ?
N7 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
N7 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
F1 B1 F2 108.81(15) . . ?
F1 B1 N1 110.43(15) . . ?
F2 B1 N1 110.87(16) . . ?
F1 B1 N2 110.45(15) . . ?
F2 B1 N2 110.44(15) . . ?
N1 B1 N2 105.83(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
C4 N1 C1 C2 0.9(2) . . . . ?
B1 N1 C1 C2 -177.65(17) . . . . ?
N1 C1 C2 C3 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 N1 C4 C3 -1.02(19) . . . . ?
B1 N1 C4 C3 177.50(16) . . . . ?
C1 N1 C4 C5 -175.90(16) . . . . ?
B1 N1 C4 C5 2.6(3) . . . . ?
C2 C3 C4 N1 0.81(19) . . . . ?
C2 C3 C4 C5 175.01(18) . . . . ?
N1 C4 C5 C6 4.6(2) . . . . ?
C3 C4 C5 C6 -168.93(17) . . . . ?
N1 C4 C5 C10 -174.23(15) . . . . ?
C3 C4 C5 C10 12.2(3) . . . . ?
C9 N2 C6 C5 -177.54(15) . . . . ?
B1 N2 C6 C5 -2.7(2) . . . . ?
C9 N2 C6 C7 -0.11(18) . . . . ?
B1 N2 C6 C7 174.71(15) . . . . ?
C4 C5 C6 N2 -4.6(2) . . . . ?
C10 C5 C6 N2 174.28(14) . . . . ?
C4 C5 C6 C7 178.73(17) . . . . ?
C10 C5 C6 C7 -2.4(3) . . . . ?
N2 C6 C7 C8 0.76(18) . . . . ?
C5 C6 C7 C8 177.79(17) . . . . ?
C6 C7 C8 C9 -1.08(19) . . . . ?
C6 N2 C9 C8 -0.57(19) . . . . ?
B1 N2 C9 C8 -175.40(16) . . . . ?
C7 C8 C9 N2 1.1(2) . . . . ?
C6 C5 C10 C15 47.3(2) . . . . ?
C4 C5 C10 C15 -133.82(17) . . . . ?
C6 C5 C10 C11 -131.92(17) . . . . ?
C4 C5 C10 C11 46.9(2) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C5 C10 C11 C12 179.12(15) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C16 N3 C13 C12 5.1(2) . . . . ?
C18 N3 C13 C12 177.74(15) . . . . ?
C16 N3 C13 C14 -175.44(15) . . . . ?
C18 N3 C13 C14 -2.8(2) . . . . ?
C11 C12 C13 N3 177.70(15) . . . . ?
C11 C12 C13 C14 -1.8(2) . . . . ?
N3 C13 C14 C15 -179.72(15) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C10 2.1(3) . . . . ?
C11 C10 C15 C14 -1.9(2) . . . . ?
C5 C10 C15 C14 178.85(15) . . . . ?
C13 N3 C16 C17 81.12(19) . . . . ?
C18 N3 C16 C17 -91.78(17) . . . . ?
N5 N4 C17 C16 -133.73(16) . . . . ?
N3 C16 C17 N4 -173.30(14) . . . . ?
C13 N3 C18 C19 83.32(18) . . . . ?
C16 N3 C18 C19 -103.79(17) . . . . ?
N8 N7 C19 C18 -77.43(19) . . . . ?
N3 C18 C19 N7 62.20(18) . . . . ?
C1 N1 B1 F1 -70.5(2) . . . . ?
C4 N1 B1 F1 111.30(18) . . . . ?
C1 N1 B1 F2 50.2(2) . . . . ?
C4 N1 B1 F2 -128.02(17) . . . . ?
C1 N1 B1 N2 170.00(17) . . . . ?
C4 N1 B1 N2 -8.3(2) . . . . ?
C9 N2 B1 F1 62.7(2) . . . . ?
C6 N2 B1 F1 -111.21(18) . . . . ?
C9 N2 B1 F2 -57.7(2) . . . . ?
C6 N2 B1 F2 128.37(17) . . . . ?
C9 N2 B1 N1 -177.77(15) . . . . ?
C6 N2 B1 N1 8.3(2) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.064

