# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tc
_database_code_depnum_ccdc_archive 'CCDC 1408052'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 B F2 N3'
_chemical_formula_sum            'C13 H10 B F2 N3'
_chemical_formula_weight         257.05

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   c_c

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   16.361(3)
_cell_length_b                   10.108(2)
_cell_length_c                   7.3990(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.88(3)
_cell_angle_gamma                90.00
_cell_volume                     1143.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1970
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      29.1

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5016
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.1344
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1982
_reflns_number_gt                1421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CAMERON (Watkin, Prout & Pearce,  1996)'
_computing_publication_material  
'CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0507P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3.1(13)
_refine_ls_number_reflns         1982
_refine_ls_number_parameters     172
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.910
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43337(16) 0.8287(2) 0.5031(3) 0.0320(7) Uani 1 1 d . . .
F2 F 0.50855(16) 0.8349(2) 0.2995(3) 0.0325(6) Uani 1 1 d . . .
N1 N 0.4535(2) 0.6241(3) 0.3591(4) 0.0153(7) Uani 1 1 d . . .
N2 N 0.3529(2) 0.7950(3) 0.1631(4) 0.0175(8) Uani 1 1 d . . .
C7 C 0.2251(3) 0.7550(4) -0.0810(5) 0.0190(9) Uani 1 1 d . . .
H7A H 0.1749 0.7113 -0.1672 0.023 Uiso 1 1 calc R . .
C6 C 0.2917(3) 0.6960(3) 0.0767(5) 0.0141(9) Uani 1 1 d . . .
C3 C 0.4258(3) 0.4057(4) 0.3548(5) 0.0170(9) Uani 1 1 d . . .
H3A H 0.3972 0.3224 0.3275 0.020 Uiso 1 1 calc R . .
N3 N 0.1541(2) 0.4869(4) -0.0188(4) 0.0216(8) Uani 1 1 d . . .
H3B H 0.1293 0.5625 -0.0091 0.026 Uiso 1 1 calc R . .
C5 C 0.3085(3) 0.5629(4) 0.1339(5) 0.0158(9) Uani 1 1 d . . .
C8 C 0.2455(3) 0.8873(4) -0.0882(5) 0.0220(10) Uani 1 1 d . . .
H8A H 0.2121 0.9511 -0.1789 0.026 Uiso 1 1 calc R . .
C1 C 0.5242(3) 0.5644(4) 0.4814(5) 0.0195(9) Uani 1 1 d . . .
H1A H 0.5765 0.6081 0.5578 0.023 Uiso 1 1 calc R . .
C4 C 0.3904(3) 0.5265(4) 0.2751(5) 0.0157(9) Uani 1 1 d . . .
C11 C 0.2546(3) 0.3318(4) 0.0032(5) 0.0174(9) Uani 1 1 d . . .
H11A H 0.3087 0.2870 0.0309 0.021 Uiso 1 1 calc R . .
C10 C 0.2438(3) 0.4636(4) 0.0485(5) 0.0154(9) Uani 1 1 d . . .
C9 C 0.3247(3) 0.9089(4) 0.0637(6) 0.0252(10) Uani 1 1 d . . .
H9A H 0.3544 0.9913 0.0930 0.030 Uiso 1 1 calc R . .
C2 C 0.5102(3) 0.4286(4) 0.4810(5) 0.0204(10) Uani 1 1 d . . .
H2A H 0.5509 0.3640 0.5534 0.025 Uiso 1 1 calc R . .
C13 C 0.1106(3) 0.3750(4) -0.1019(6) 0.0319(12) Uani 1 1 d . . .
H13A H 0.0489 0.3657 -0.1583 0.038 Uiso 1 1 calc R . .
C12 C 0.1712(3) 0.2775(4) -0.0903(5) 0.0250(11) Uani 1 1 d . . .
H12A H 0.1588 0.1895 -0.1372 0.030 Uiso 1 1 calc R . .
B1 B 0.4389(3) 0.7756(5) 0.3327(6) 0.0215(11) 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 1.403(5) . ?
F2 B1 1.384(5) . ?
N1 C1 1.332(5) . ?
N1 C4 1.403(5) . ?
N1 B1 1.552(5) . ?
N2 C9 1.356(5) . ?
N2 C6 1.398(5) . ?
N2 B1 1.528(5) . ?
C7 C8 1.384(5) . ?
C7 C6 1.414(5) . ?
C7 H7A 0.9500 . ?
C6 C5 1.408(5) . ?
C3 C2 1.383(5) . ?
C3 C4 1.390(5) . ?
C3 H3A 0.9500 . ?
N3 C13 1.361(5) . ?
N3 C10 1.392(5) . ?
N3 H3B 0.8800 . ?
C5 C4 1.423(5) . ?
C5 C10 1.432(5) . ?
C8 C9 1.397(6) . ?
C8 H8A 0.9500 . ?
C1 C2 1.391(5) . ?
C1 H1A 0.9500 . ?
C11 C10 1.400(5) . ?
C11 C12 1.402(6) . ?
C11 H11A 0.9500 . ?
C9 H9A 0.9500 . ?
C2 H2A 0.9500 . ?
C13 C12 1.379(6) . ?
C13 H13A 0.9500 . ?
C12 H12A 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
C1 N1 C4 107.9(3) . . ?
C1 N1 B1 126.2(3) . . ?
C4 N1 B1 125.6(3) . . ?
C9 N2 C6 108.0(3) . . ?
C9 N2 B1 126.2(3) . . ?
C6 N2 B1 125.7(3) . . ?
C8 C7 C6 108.2(4) . . ?
C8 C7 H7A 125.9 . . ?
C6 C7 H7A 125.9 . . ?
N2 C6 C5 121.0(3) . . ?
N2 C6 C7 107.0(3) . . ?
C5 C6 C7 131.4(3) . . ?
C2 C3 C4 107.7(4) . . ?
C2 C3 H3A 126.1 . . ?
C4 C3 H3A 126.1 . . ?
C13 N3 C10 109.6(4) . . ?
C13 N3 H3B 125.2 . . ?
C10 N3 H3B 125.2 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 C10 120.3(3) . . ?
C4 C5 C10 119.8(3) . . ?
C7 C8 C9 106.7(4) . . ?
C7 C8 H8A 126.6 . . ?
C9 C8 H8A 126.6 . . ?
N1 C1 C2 110.0(4) . . ?
N1 C1 H1A 125.0 . . ?
C2 C1 H1A 125.0 . . ?
C3 C4 N1 107.4(3) . . ?
C3 C4 C5 132.8(4) . . ?
N1 C4 C5 119.7(3) . . ?
C10 C11 C12 107.9(4) . . ?
C10 C11 H11A 126.0 . . ?
C12 C11 H11A 126.0 . . ?
N3 C10 C11 106.4(4) . . ?
N3 C10 C5 123.9(3) . . ?
C11 C10 C5 129.6(4) . . ?
N2 C9 C8 110.0(4) . . ?
N2 C9 H9A 125.0 . . ?
C8 C9 H9A 125.0 . . ?
C3 C2 C1 106.9(4) . . ?
C3 C2 H2A 126.6 . . ?
C1 C2 H2A 126.6 . . ?
N3 C13 C12 108.5(4) . . ?
N3 C13 H13A 125.8 . . ?
C12 C13 H13A 125.8 . . ?
C13 C12 C11 107.6(4) . . ?
C13 C12 H12A 126.2 . . ?
C11 C12 H12A 126.2 . . ?
F2 B1 F1 108.4(3) . . ?
F2 B1 N2 112.0(3) . . ?
F1 B1 N2 110.7(4) . . ?
F2 B1 N1 110.5(4) . . ?
F1 B1 N1 108.7(3) . . ?
N2 B1 N1 106.6(3) . . ?

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
C9 N2 C6 C5 172.2(3) . . . . ?
B1 N2 C6 C5 -4.5(5) . . . . ?
C9 N2 C6 C7 0.3(4) . . . . ?
B1 N2 C6 C7 -176.5(4) . . . . ?
C8 C7 C6 N2 -0.4(4) . . . . ?
C8 C7 C6 C5 -171.2(4) . . . . ?
N2 C6 C5 C4 -3.0(5) . . . . ?
C7 C6 C5 C4 166.7(4) . . . . ?
N2 C6 C5 C10 177.8(3) . . . . ?
C7 C6 C5 C10 -12.5(6) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C4 N1 C1 C2 0.3(4) . . . . ?
B1 N1 C1 C2 173.4(3) . . . . ?
C2 C3 C4 N1 -1.8(4) . . . . ?
C2 C3 C4 C5 177.4(4) . . . . ?
C1 N1 C4 C3 1.0(4) . . . . ?
B1 N1 C4 C3 -172.2(3) . . . . ?
C1 N1 C4 C5 -178.4(3) . . . . ?
B1 N1 C4 C5 8.5(5) . . . . ?
C6 C5 C4 C3 -178.1(3) . . . . ?
C10 C5 C4 C3 1.1(6) . . . . ?
C6 C5 C4 N1 1.1(5) . . . . ?
C10 C5 C4 N1 -179.7(3) . . . . ?
C13 N3 C10 C11 0.2(4) . . . . ?
C13 N3 C10 C5 176.3(3) . . . . ?
C12 C11 C10 N3 -0.1(4) . . . . ?
C12 C11 C10 C5 -176.0(3) . . . . ?
C6 C5 C10 N3 -30.4(5) . . . . ?
C4 C5 C10 N3 150.4(3) . . . . ?
C6 C5 C10 C11 144.8(4) . . . . ?
C4 C5 C10 C11 -34.3(6) . . . . ?
C6 N2 C9 C8 -0.1(4) . . . . ?
B1 N2 C9 C8 176.7(4) . . . . ?
C7 C8 C9 N2 -0.2(4) . . . . ?
C4 C3 C2 C1 2.0(4) . . . . ?
N1 C1 C2 C3 -1.4(4) . . . . ?
C10 N3 C13 C12 -0.2(4) . . . . ?
N3 C13 C12 C11 0.1(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C9 N2 B1 F2 -43.6(5) . . . . ?
C6 N2 B1 F2 132.6(4) . . . . ?
C9 N2 B1 F1 77.5(5) . . . . ?
C6 N2 B1 F1 -106.3(4) . . . . ?
C9 N2 B1 N1 -164.5(3) . . . . ?
C6 N2 B1 N1 11.7(5) . . . . ?
C1 N1 B1 F2 52.5(5) . . . . ?
C4 N1 B1 F2 -135.6(4) . . . . ?
C1 N1 B1 F1 -66.3(5) . . . . ?
C4 N1 B1 F1 105.6(4) . . . . ?
C1 N1 B1 N2 174.4(3) . . . . ?
C4 N1 B1 N2 -13.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B F2 0.88 2.23 2.906(4) 132.9 4_464

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1408053'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;
_audit_creation_date             2015-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 B F2 N3'
_chemical_formula_sum            'C14 H12 B F2 N3'
_chemical_formula_weight         271.08
_chemical_absolute_configuration ?
_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'
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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.531(4)
_cell_length_b                   9.714(4)
_cell_length_c                   15.674(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1298.9(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_process_details   'NUMABS (RIGAKU 1999)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1761
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23878
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         4.107
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   ?
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1943
_reflns_number_total             2278
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0798P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1452
_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.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C13(H13), C2(H2), C11(H11), C12(H12), C1(H1), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F1 F 0.8064(3) 0.5762(3) 0.28561(18) 0.0233(7) Uani 1 1 d . . . . .
F2 F 0.5871(3) 0.5686(3) 0.20525(17) 0.0253(7) Uani 1 1 d . . . . .
N3 N 0.5890(5) 0.1907(4) 0.5498(3) 0.0177(10) Uani 1 1 d . . . . .
N1 N 0.6847(5) 0.3541(4) 0.2623(2) 0.0193(10) Uani 1 1 d . . . . .
N2 N 0.5619(5) 0.5263(4) 0.3564(3) 0.0203(10) Uani 1 1 d . . . . .
C4 C 0.6598(6) 0.2545(5) 0.3253(3) 0.0184(11) Uani 1 1 d . . . . .
C10 C 0.5580(6) 0.1787(5) 0.4645(3) 0.0186(11) Uani 1 1 d . . . . .
C7 C 0.4350(6) 0.4777(6) 0.4794(3) 0.0216(12) Uani 1 1 d . . . . .
H7 H 0.3983 0.4319 0.5275 0.026 Uiso 1 1 calc R . . . .
C14 C 0.6816(6) 0.2968(5) 0.5933(3) 0.0217(12) Uani 1 1 d . . . . .
H14A H 0.7401 0.3484 0.5519 0.033 Uiso 1 1 calc GR . . . .
H14B H 0.7525 0.2539 0.6327 0.033 Uiso 1 1 calc GR . . . .
H14C H 0.6126 0.3576 0.6237 0.033 Uiso 1 1 calc GR . . . .
C3 C 0.7182(6) 0.1288(5) 0.2920(3) 0.0223(12) Uani 1 1 d . . . . .
H3 H 0.7168 0.0440 0.3196 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5861(6) 0.2872(5) 0.4018(3) 0.0173(11) Uani 1 1 d . . . . .
C13 C 0.5457(6) 0.0709(5) 0.5894(3) 0.0207(11) Uani 1 1 d . . . . .
H13 H 0.5554 0.0524 0.6473 0.025 Uiso 1 1 calc R . . . .
C2 C 0.7764(6) 0.1536(6) 0.2128(3) 0.0259(12) Uani 1 1 d . . . . .
H2 H 0.8222 0.0895 0.1765 0.031 Uiso 1 1 calc R . . . .
C11 C 0.4947(6) 0.0493(5) 0.4504(4) 0.0200(11) Uani 1 1 d . . . . .
H11 H 0.4640 0.0134 0.3980 0.024 Uiso 1 1 calc R . . . .
C12 C 0.4855(6) -0.0174(6) 0.5292(4) 0.0239(12) Uani 1 1 d . . . . .
H12 H 0.4460 -0.1052 0.5391 0.029 Uiso 1 1 calc R . . . .
C1 C 0.7544(6) 0.2931(6) 0.1964(3) 0.0241(12) Uani 1 1 d . . . . .
H1 H 0.7843 0.3375 0.1464 0.029 Uiso 1 1 calc R . . . .
C6 C 0.5342(6) 0.4243(5) 0.4170(3) 0.0189(11) Uani 1 1 d . . . . .
C8 C 0.4012(7) 0.6130(5) 0.4560(4) 0.0266(13) Uani 1 1 d . . . . .
H8 H 0.3370 0.6741 0.4853 0.032 Uiso 1 1 calc R . . . .
C9 C 0.4811(6) 0.6393(6) 0.3810(3) 0.0253(13) Uani 1 1 d . . . . .
H9 H 0.4795 0.7226 0.3518 0.030 Uiso 1 1 calc R . . . .
B1 B 0.6613(7) 0.5115(6) 0.2747(4) 0.0196(13) 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 1.400(7) . ?
F2 B1 1.376(7) . ?
N3 C10 1.367(7) . ?
N3 C14 1.467(6) . ?
N3 C13 1.369(6) . ?
N1 C4 1.400(6) . ?
N1 C1 1.330(7) . ?
N1 B1 1.554(7) . ?
N2 C6 1.393(7) . ?
N2 C9 1.352(7) . ?
N2 B1 1.543(7) . ?
C4 C3 1.418(7) . ?
C4 C5 1.390(7) . ?
C10 C5 1.461(7) . ?
C10 C11 1.386(7) . ?
C7 C6 1.393(7) . ?
C7 C8 1.395(7) . ?
C3 C2 1.358(7) . ?
C5 C6 1.424(7) . ?
C13 C12 1.375(8) . ?
C2 C1 1.393(8) . ?
C11 C12 1.397(8) . ?
C8 C9 1.381(8) . ?

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
C10 N3 C14 128.2(4) . . ?
C10 N3 C13 108.6(4) . . ?
C13 N3 C14 122.1(4) . . ?
C4 N1 B1 124.9(4) . . ?
C1 N1 C4 108.0(4) . . ?
C1 N1 B1 126.3(4) . . ?
C6 N2 B1 126.3(4) . . ?
C9 N2 C6 107.2(4) . . ?
C9 N2 B1 126.4(4) . . ?
N1 C4 C3 106.3(4) . . ?
C5 C4 N1 121.3(4) . . ?
C5 C4 C3 132.3(5) . . ?
N3 C10 C5 124.4(4) . . ?
N3 C10 C11 108.0(5) . . ?
C11 C10 C5 127.6(5) . . ?
C6 C7 C8 107.0(5) . . ?
C2 C3 C4 108.2(5) . . ?
C4 C5 C10 119.3(4) . . ?
C4 C5 C6 119.9(5) . . ?
C6 C5 C10 120.7(5) . . ?
N3 C13 C12 108.6(5) . . ?
C3 C2 C1 107.0(5) . . ?
C10 C11 C12 107.5(5) . . ?
C13 C12 C11 107.2(5) . . ?
N1 C1 C2 110.5(4) . . ?
N2 C6 C7 108.4(4) . . ?
N2 C6 C5 119.9(5) . . ?
C7 C6 C5 130.9(5) . . ?
C9 C8 C7 107.2(5) . . ?
N2 C9 C8 110.1(5) . . ?
F1 B1 N1 110.1(4) . . ?
F1 B1 N2 110.0(4) . . ?
F2 B1 F1 108.8(4) . . ?
F2 B1 N1 110.9(4) . . ?
F2 B1 N2 111.5(4) . . ?
N2 B1 N1 105.5(4) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
