# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_tmp1byf
_database_code_depnum_ccdc_archive 'CCDC 1856378'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H13 N2, B F4, 2(H2 O)'
_chemical_formula_sum            'C8 H17 B F4 N2 O2'
_chemical_formula_weight         260.04

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'
O O 0.0106 0.0060 '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                   7.469(5)
_cell_length_b                   8.644(5)
_cell_length_c                   10.230(7)
_cell_angle_alpha                88.12(5)
_cell_angle_beta                 88.89(5)
_cell_angle_gamma                71.28(6)
_cell_volume                     625.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2427
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'KM4 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3877
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.880
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2367
_reflns_number_gt                1748
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.1652P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2367
_refine_ls_number_parameters     198
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2205
_refine_ls_wR_factor_gt          0.2072
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.056
_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
N1 N 0.7692(2) 0.5668(2) 0.64908(17) 0.0289(5) Uani 1 1 d . . . . .
H1 H 0.775573 0.585435 0.564304 0.035 Uiso 1 1 calc R U . . .
N2 N 0.7494(3) 0.5103(2) 0.90801(17) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.7393(3) 0.4281(2) 0.6892(2) 0.0297(5) Uani 1 1 d . . . . .
C3 C 0.7295(3) 0.4005(3) 0.8239(2) 0.0311(5) Uani 1 1 d . . . . .
C4 C 0.7787(3) 0.6473(3) 0.8637(2) 0.0300(5) Uani 1 1 d . . . . .
C5 C 0.7903(3) 0.6796(3) 0.7294(2) 0.0296(5) Uani 1 1 d . . . . .
C6 C 0.7208(4) 0.3130(3) 0.5889(2) 0.0404(6) Uani 1 1 d . . . . .
H6A H 0.716412 0.364365 0.501641 0.061 Uiso 1 1 calc R U . . .
H6B H 0.604169 0.286303 0.605142 0.061 Uiso 1 1 calc R U . . .
H6C H 0.829535 0.212781 0.593921 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6986(4) 0.2488(3) 0.8790(3) 0.0423(6) Uani 1 1 d . . . . .
H7A H 0.812649 0.155241 0.865338 0.063 Uiso 1 1 calc R U . . .
H7B H 0.591752 0.231114 0.834910 0.063 Uiso 1 1 calc R U . . .
H7C H 0.671056 0.260667 0.972869 0.063 Uiso 1 1 calc R U . . .
C8 C 0.7953(4) 0.7674(3) 0.9604(2) 0.0407(6) Uani 1 1 d . . . . .
H8A H 0.683148 0.864946 0.955669 0.061 Uiso 1 1 calc R U . . .
H8B H 0.908409 0.798206 0.940254 0.061 Uiso 1 1 calc R U . . .
H8C H 0.805373 0.718062 1.048674 0.061 Uiso 1 1 calc R U . . .
C9 C 0.8217(4) 0.8288(3) 0.6712(2) 0.0392(6) Uani 1 1 d . . . . .
H9A H 0.855442 0.811986 0.578473 0.059 Uiso 1 1 calc R U . . .
H9B H 0.924639 0.850610 0.717137 0.059 Uiso 1 1 calc R U . . .
H9C H 0.705810 0.922005 0.679592 0.059 Uiso 1 1 calc R U . . .
O1 O 0.7979(3) 0.6290(2) 0.38911(16) 0.0463(5) Uani 1 1 d G . . . .
H1A H 0.769001 0.724179 0.353845 0.069 Uiso 1 1 d G U . . .
H1B H 0.790896 0.567803 0.327408 0.069 Uiso 1 1 d G U . . .
O2 O 0.7443(3) 0.4516(2) 0.19070(17) 0.0501(5) Uani 1 1 d G . . . .
H2A H 0.735845 0.356911 0.206113 0.075 Uiso 1 1 d G U . . .
H2B H 0.746183 0.460714 0.107728 0.075 Uiso 1 1 d G U . . .
B B 0.7285(4) 0.0379(3) 0.2644(3) 0.0386(7) Uani 1 1 d . . . . .
F1 F 0.6138(6) -0.0517(6) 0.2376(5) 0.0682(12) Uani 0.795(10) 1 d D . P A 1
F2 F 0.6296(3) 0.1964(3) 0.2978(4) 0.0590(11) Uani 0.795(10) 1 d D . P A 1
F3 F 0.8427(6) -0.0354(6) 0.3668(4) 0.0865(14) Uani 0.795(10) 1 d D . P A 1
F4 F 0.8490(5) 0.0431(5) 0.1584(3) 0.0594(10) Uani 0.795(10) 1 d D . P A 1
F1A F 0.583(2) 0.015(2) 0.1880(16) 0.060(5) Uiso 0.129(6) 1 d D . P A 2
F2A F 0.778(3) 0.121(3) 0.175(2) 0.091(8) Uiso 0.129(6) 1 d D . P A 2
F3A F 0.625(2) 0.128(2) 0.3718(18) 0.068(5) Uiso 0.129(6) 1 d D . P A 2
F4A F 0.862(3) -0.082(2) 0.314(2) 0.072(7) Uiso 0.129(6) 1 d D . P A 2
F1B F 0.578(6) -0.043(6) 0.212(5) 0.0682(12) Uani 0.076(8) 1 d D . P A 3
F2B F 0.621(3) 0.186(3) 0.237(3) 0.034(6) Uiso 0.076(8) 1 d D . P A 3
F3B F 0.721(7) -0.031(4) 0.386(3) 0.105(14) Uiso 0.076(8) 1 d D . P A 3
F4B F 0.881(3) -0.022(4) 0.210(4) 0.064(9) Uiso 0.076(8) 1 d D . P A 3


_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
N1 C2 1.339(3) . ?
N1 C5 1.344(3) . ?
N1 H1 0.8800 . ?
N2 C4 1.334(3) . ?
N2 C3 1.347(3) . ?
C2 C3 1.395(3) . ?
C2 C6 1.491(3) . ?
C3 C7 1.493(3) . ?
C4 C5 1.400(3) . ?
C4 C8 1.492(3) . ?
C5 C9 1.487(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O1 H1A 0.8501 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8502 . ?
B F4B 1.22(2) . ?
B F2A 1.269(19) . ?
B F4A 1.285(19) . ?
B F2B 1.29(2) . ?
B F1 1.363(4) . ?
B F3 1.368(4) . ?
B F3B 1.37(3) . ?
B F2 1.382(4) . ?
B F4 1.404(4) . ?
B F1A 1.418(16) . ?
B F3A 1.432(15) . ?
B F1B 1.61(3) . ?

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
C2 N1 C5 124.48(19) . . ?
C2 N1 H1 117.8 . . ?
C5 N1 H1 117.8 . . ?
C4 N2 C3 120.49(19) . . ?
N1 C2 C3 117.08(19) . . ?
N1 C2 C6 118.6(2) . . ?
C3 C2 C6 124.3(2) . . ?
N2 C3 C2 120.5(2) . . ?
N2 C3 C7 118.2(2) . . ?
C2 C3 C7 121.4(2) . . ?
N2 C4 C5 120.95(19) . . ?
N2 C4 C8 118.7(2) . . ?
C5 C4 C8 120.4(2) . . ?
N1 C5 C4 116.55(19) . . ?
N1 C5 C9 118.7(2) . . ?
C4 C5 C9 124.7(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H1A O1 H1B 104.5 . . ?
H2A O2 H2B 104.5 . . ?
F2A B F4A 115.9(14) . . ?
F4B B F2B 122.1(19) . . ?
F1 B F3 109.0(3) . . ?
F4B B F3B 112.4(19) . . ?
F2B B F3B 120.0(17) . . ?
F1 B F2 113.1(3) . . ?
F3 B F2 108.0(4) . . ?
F1 B F4 111.6(3) . . ?
F3 B F4 106.4(3) . . ?
F2 B F4 108.5(3) . . ?
F2A B F1A 93.2(11) . . ?
F4A B F1A 122.5(11) . . ?
F2A B F3A 115.8(13) . . ?
F4A B F3A 106.5(11) . . ?
F1A B F3A 102.4(9) . . ?
F4B B F1B 110(2) . . ?
F2B B F1B 93.5(19) . . ?
F3B B F1B 90(2) . . ?

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
C5 N1 C2 C3 0.0(3) . . . . ?
C5 N1 C2 C6 -179.29(18) . . . . ?
C4 N2 C3 C2 0.1(3) . . . . ?
C4 N2 C3 C7 179.5(2) . . . . ?
N1 C2 C3 N2 0.1(3) . . . . ?
C6 C2 C3 N2 179.38(19) . . . . ?
N1 C2 C3 C7 -179.3(2) . . . . ?
C6 C2 C3 C7 0.0(3) . . . . ?
C3 N2 C4 C5 -0.4(3) . . . . ?
C3 N2 C4 C8 178.5(2) . . . . ?
C2 N1 C5 C4 -0.3(3) . . . . ?
C2 N1 C5 C9 -179.6(2) . . . . ?
N2 C4 C5 N1 0.5(3) . . . . ?
C8 C4 C5 N1 -178.42(19) . . . . ?
N2 C4 C5 C9 179.7(2) . . . . ?
C8 C4 C5 C9 0.8(3) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.88 1.83 2.714(3) 177.1 . yes
O1 H1B O2 0.85 1.85 2.695(3) 172.7 . yes
O2 H2A F2^a 0.85 2.01 2.796(4) 154.0 . yes
O2 H2A F2A^b 0.85 1.99 2.79(2) 156.5 . yes
O2 H2A F2B^c 0.85 1.95 2.76(2) 159.4 . yes
O1 H1A F3^a 0.85 2.32 3.025(5) 140.2 1_565 yes
O1 H1A F3B^c 0.85 2.07 2.81(3) 145.2 1_565 yes
O1 H1A F4A^b 0.85 2.03 2.77(2) 144.4 1_565 yes

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_ct1
_database_code_depnum_ccdc_archive 'CCDC 1856380'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 B2 F8 N4'
_chemical_formula_weight         448.03

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P c n b'
_space_group_name_Hall           '-P 2b 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, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0340(4)
_cell_length_b                   15.2270(5)
_cell_length_c                   24.4497(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4107.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7738
_cell_measurement_theta_min      3.1012
_cell_measurement_theta_max      36.6942

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_method       ω
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            30394
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_max         36.780
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.565
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.565
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5822
_reflns_number_gt                3193
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0980P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5822
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   0.910
_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_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
F5 F 0.70508(10) 0.65384(7) 0.31226(4) 0.0318(3) Uani 1 1 d . . . . .
F8 F 0.71262(11) 0.57481(7) 0.23351(4) 0.0323(3) Uani 1 1 d . . . . .
F6 F 0.71938(12) 0.72339(7) 0.23056(5) 0.0428(3) Uani 1 1 d . . . . .
F7 F 0.87853(10) 0.64658(9) 0.26397(6) 0.0488(4) Uani 1 1 d . . . . .
B2 B 0.75366(17) 0.64993(13) 0.25996(8) 0.0191(4) Uani 1 1 d . . . . .
F2 F 0.69523(11) 0.34459(7) -0.05950(5) 0.0374(3) Uani 1 1 d . . . . .
F1 F 0.70783(10) 0.42550(7) 0.01832(4) 0.0304(3) Uani 1 1 d . . . . .
F4 F 0.87719(10) 0.37043(7) -0.02083(5) 0.0371(3) Uani 1 1 d . . . . .
F3 F 0.74472(11) 0.27898(8) 0.02111(5) 0.0399(3) Uani 1 1 d . . . . .
B1 B 0.75524(18) 0.35420(13) -0.01021(8) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.19987(14) 0.45922(10) 0.08293(6) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.19878(14) 0.54560(10) 0.16413(6) 0.0156(3) Uani 1 1 d . . . . .
N1 N 0.14285(12) 0.50546(8) 0.12210(5) 0.0151(3) Uani 1 1 d . . . . .
H1 H 0.063443 0.509763 0.120109 0.026(5) Uiso 1 1 calc R . . . .
N3 N 0.63841(12) 0.49690(8) 0.12707(5) 0.0149(3) Uani 1 1 d . . . . .
H3 H 0.558774 0.494391 0.128243 0.034(6) Uiso 1 1 calc R . . . .
N2 N 0.38531(12) 0.49267(8) 0.12799(5) 0.0152(3) Uani 1 1 d . . . . .
N4 N 0.88133(12) 0.50449(8) 0.12319(5) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.70001(14) 0.42258(10) 0.13675(6) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.32494(14) 0.53738(10) 0.16667(6) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.32619(14) 0.45412(10) 0.08631(6) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.68942(14) 0.57485(10) 0.11573(6) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.82660(14) 0.42761(11) 0.13424(6) 0.0157(3) Uani 1 1 d . . . . .
C31 C 0.39483(15) 0.57720(11) 0.21288(7) 0.0205(4) Uani 1 1 d . . . . .
H31A H 0.379996 0.640631 0.213943 0.031 Uiso 1 1 calc R U . . .
H31B H 0.481548 0.566311 0.207499 0.031 Uiso 1 1 calc R U . . .
H31C H 0.368712 0.550730 0.247462 0.031 Uiso 1 1 calc R U . . .
C61 C 0.90404(15) 0.34770(11) 0.14194(7) 0.0216(4) Uani 1 1 d . . . . .
H61A H 0.902217 0.312053 0.108581 0.032 Uiso 1 1 calc R U . . .
H61B H 0.872941 0.313094 0.172685 0.032 Uiso 1 1 calc R U . . .
H61C H 0.987606 0.365706 0.149602 0.032 Uiso 1 1 calc R U . . .
C51 C 0.63085(15) 0.34022(11) 0.14760(7) 0.0192(4) Uani 1 1 d . . . . .
H51A H 0.546700 0.354869 0.156620 0.029 Uiso 1 1 calc R U . . .
H51B H 0.667861 0.308824 0.178347 0.029 Uiso 1 1 calc R U . . .
H51C H 0.632540 0.302864 0.114972 0.029 Uiso 1 1 calc R U . . .
C21 C 0.39788(15) 0.40656(12) 0.04394(7) 0.0203(4) Uani 1 1 d . . . . .
H21A H 0.375022 0.344366 0.043918 0.030 Uiso 1 1 calc R U . . .
H21B H 0.484474 0.412039 0.052170 0.030 Uiso 1 1 calc R U . . .
H21C H 0.381256 0.432007 0.007902 0.030 Uiso 1 1 calc R U . . .
C11 C 0.12650(15) 0.41810(11) 0.03862(7) 0.0202(4) Uani 1 1 d . . . . .
H11A H 0.040297 0.429304 0.045274 0.030 Uiso 1 1 calc R U . . .
H11B H 0.141121 0.354624 0.038153 0.030 Uiso 1 1 calc R U . . .
H11C H 0.149851 0.443339 0.003280 0.030 Uiso 1 1 calc R U . . .
C41 C 0.12438(14) 0.59447(12) 0.20473(7) 0.0199(4) Uani 1 1 d . . . . .
H41A H 0.038493 0.589556 0.194993 0.030 Uiso 1 1 calc R U . . .
H41B H 0.148249 0.656460 0.204723 0.030 Uiso 1 1 calc R U . . .
H41C H 0.137385 0.569582 0.241228 0.030 Uiso 1 1 calc R U . . .
C7 C 0.81621(14) 0.57760(10) 0.11429(6) 0.0155(3) Uani 1 1 d . . . . .
C81 C 0.60888(15) 0.65236(11) 0.10751(7) 0.0204(4) Uani 1 1 d . . . . .
H81A H 0.525811 0.632297 0.100789 0.031 Uiso 1 1 calc R U . . .
H81B H 0.637386 0.686408 0.076028 0.031 Uiso 1 1 calc R U . . .
H81C H 0.610493 0.689313 0.140322 0.031 Uiso 1 1 calc R U . . .
C71 C 0.88224(15) 0.66183(11) 0.10456(7) 0.0210(4) Uani 1 1 d . . . . .
H71A H 0.882067 0.696904 0.138165 0.032 Uiso 1 1 calc R U . . .
H71B H 0.841945 0.694684 0.075280 0.032 Uiso 1 1 calc R U . . .
H71C H 0.966015 0.649143 0.093846 0.032 Uiso 1 1 calc R U . . .


_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
F5 B2 1.388(2) . ?
F8 B2 1.390(2) . ?
F6 B2 1.382(2) . ?
F7 B2 1.382(2) . ?
F2 B1 1.383(2) . ?
F1 B1 1.392(2) . ?
F4 B1 1.393(2) . ?
F3 B1 1.383(2) . ?
C1 N1 1.3451(19) . ?
C1 C2 1.398(2) . ?
C1 C11 1.490(2) . ?
C4 N1 1.3455(19) . ?
C4 C3 1.399(2) . ?
C4 C41 1.488(2) . ?
N1 H1 0.8800 . ?
N3 C5 1.3411(19) . ?
N3 C8 1.3426(19) . ?
N3 H3 0.8800 . ?
N2 C3 1.3423(19) . ?
N2 C2 1.3447(19) . ?
N4 C7 1.343(2) . ?
N4 C6 1.345(2) . ?
C5 C6 1.400(2) . ?
C5 C51 1.492(2) . ?
C3 C31 1.496(2) . ?
C2 C21 1.491(2) . ?
C8 C7 1.400(2) . ?
C8 C81 1.491(2) . ?
C6 C61 1.499(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C7 C71 1.494(2) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F7 B2 F6 109.85(16) . . ?
F7 B2 F5 108.73(15) . . ?
F6 B2 F5 109.80(15) . . ?
F7 B2 F8 109.11(15) . . ?
F6 B2 F8 109.57(15) . . ?
F5 B2 F8 109.76(15) . . ?
F2 B1 F3 110.78(15) . . ?
F2 B1 F4 108.60(15) . . ?
F3 B1 F4 109.36(15) . . ?
F2 B1 F1 109.83(15) . . ?
F3 B1 F1 109.69(15) . . ?
F4 B1 F1 108.55(15) . . ?
N1 C1 C2 116.94(14) . . ?
N1 C1 C11 118.92(14) . . ?
C2 C1 C11 124.13(14) . . ?
N1 C4 C3 116.71(13) . . ?
N1 C4 C41 118.93(14) . . ?
C3 C4 C41 124.36(14) . . ?
C1 N1 C4 124.55(14) . . ?
C1 N1 H1 117.7 . . ?
C4 N1 H1 117.7 . . ?
C5 N3 C8 124.74(15) . . ?
C5 N3 H3 117.6 . . ?
C8 N3 H3 117.6 . . ?
C3 N2 C2 120.96(14) . . ?
C7 N4 C6 120.93(14) . . ?
N3 C5 C6 116.85(14) . . ?
N3 C5 C51 118.78(14) . . ?
C6 C5 C51 124.34(14) . . ?
N2 C3 C4 120.53(14) . . ?
N2 C3 C31 118.80(14) . . ?
C4 C3 C31 120.66(14) . . ?
N2 C2 C1 120.28(14) . . ?
N2 C2 C21 118.75(14) . . ?
C1 C2 C21 120.97(14) . . ?
N3 C8 C7 116.78(14) . . ?
N3 C8 C81 118.54(14) . . ?
C7 C8 C81 124.64(14) . . ?
N4 C6 C5 120.29(14) . . ?
N4 C6 C61 118.43(14) . . ?
C5 C6 C61 121.25(14) . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C6 C61 H61A 109.5 . . ?
C6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N4 C7 C8 120.38(14) . . ?
N4 C7 C71 118.46(14) . . ?
C8 C7 C71 121.13(14) . . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?

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
C2 C1 N1 C4 -0.9(2) . . . . ?
C11 C1 N1 C4 -179.98(15) . . . . ?
C3 C4 N1 C1 -0.4(2) . . . . ?
C41 C4 N1 C1 -179.84(14) . . . . ?
C8 N3 C5 C6 -0.6(2) . . . . ?
C8 N3 C5 C51 -178.66(14) . . . . ?
C2 N2 C3 C4 -0.6(2) . . . . ?
C2 N2 C3 C31 178.56(14) . . . . ?
N1 C4 C3 N2 1.2(2) . . . . ?
C41 C4 C3 N2 -179.41(15) . . . . ?
N1 C4 C3 C31 -177.98(14) . . . . ?
C41 C4 C3 C31 1.4(2) . . . . ?
C3 N2 C2 C1 -0.7(2) . . . . ?
C3 N2 C2 C21 178.97(14) . . . . ?
N1 C1 C2 N2 1.5(2) . . . . ?
C11 C1 C2 N2 -179.50(15) . . . . ?
N1 C1 C2 C21 -178.23(14) . . . . ?
C11 C1 C2 C21 0.8(2) . . . . ?
C5 N3 C8 C7 -0.3(2) . . . . ?
C5 N3 C8 C81 -178.22(14) . . . . ?
C7 N4 C6 C5 -0.1(2) . . . . ?
C7 N4 C6 C61 178.00(14) . . . . ?
N3 C5 C6 N4 0.8(2) . . . . ?
C51 C5 C6 N4 178.74(14) . . . . ?
N3 C5 C6 C61 -177.30(14) . . . . ?
C51 C5 C6 C61 0.7(2) . . . . ?
C6 N4 C7 C8 -0.8(2) . . . . ?
C6 N4 C7 C71 177.44(14) . . . . ?
N3 C8 C7 N4 0.9(2) . . . . ?
C81 C8 C7 N4 178.76(14) . . . . ?
N3 C8 C7 C71 -177.21(14) . . . . ?
C81 C8 C7 C71 0.6(2) . . . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_tmpbf250
_database_code_depnum_ccdc_archive 'CCDC 1856379'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N2, 2(B F4)'
_chemical_formula_sum            'C8 H14 B2 F8 N2'
_chemical_formula_weight         311.83

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   9.790(4)
_cell_length_b                   12.442(5)
_cell_length_c                   11.160(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1359.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    3133
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      31.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'KM4 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9372
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.216
_diffrn_reflns_theta_max         36.916
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1709
_reflns_number_gt                964
_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       'CrysAlis CCD, Agilent Technologies, 2010'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS(Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1490P)²+0.1540P] 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         1709
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2722
_refine_ls_wR_factor_gt          0.2256
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.500000 0.59054(12) 0.44117(13) 0.0520(4) Uani 1 2 d S T P . .
H1 H 0.500000 0.651150 0.402302 0.062 Uiso 1 2 calc R U P . .
C1 C 0.37842(13) 0.54801(10) 0.46845(11) 0.0521(4) Uani 1 1 d . . . . .
C2 C 0.25153(18) 0.60408(16) 0.43060(19) 0.0763(5) Uani 1 1 d . . . . .
H21 H 0.198420 0.557115 0.379196 0.114 Uiso 1 1 calc R U . . .
H22 H 0.275185 0.668960 0.387103 0.114 Uiso 1 1 calc R U . . .
H23 H 0.198152 0.622770 0.500802 0.114 Uiso 1 1 calc R U . . .
B B 0.500000 0.8413(2) 0.2539(2) 0.0654(6) Uani 1 2 d S T P . .
F11 F 0.500000 0.8008(7) 0.3681(6) 0.120(3) Uani 0.62(2) 2 d S T P A 1
F21 F 0.4353(15) 0.7955(10) 0.1696(8) 0.136(4) Uani 0.312(11) 1 d . . P A 1
F31 F 0.6278(13) 0.8681(13) 0.2141(16) 0.148(5) Uani 0.312(11) 1 d . . P A 1
F41 F 0.4408(17) 0.9309(9) 0.2466(11) 0.138(5) Uani 0.312(11) 1 d . . P A 1
F12 F 0.500000 0.9452(12) 0.274(2) 0.212(14) Uani 0.38(2) 2 d S T P A 2
F22 F 0.4744(18) 0.7888(7) 0.3586(12) 0.111(6) Uani 0.188(11) 1 d . . P A 2
F32 F 0.500000 0.7500(16) 0.199(3) 0.219(10) Uani 0.38(2) 2 d S T P A 2
F42 F 0.6425(19) 0.822(2) 0.231(3) 0.137(6) Uani 0.188(11) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3376(16) 12_655 ?
N1 C1 1.3377(16) . ?
N1 H1 0.8700 . ?
C1 C1 1.387(3) 4_566 ?
C1 C2 1.486(2) . ?
C2 H21 0.9700 . ?
C2 H22 0.9700 . ?
C2 H23 0.9700 . ?
B F41 1.259(6) . ?
B F21 1.270(6) . ?
B F32 1.293(13) . ?
B F12 1.311(17) . ?
B F22 1.362(8) . ?
B F31 1.369(9) . ?
B F11 1.370(6) . ?
F32 F42 1.70(3) . ?

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 C1 125.69(16) 12_655 . ?
C1 N1 H1 117.2 12_655 . ?
C1 N1 H1 117.2 . . ?
N1 C1 C1 117.15(8) . 4_566 ?
N1 C1 C2 119.57(14) . . ?
C1 C1 C2 123.28(10) 4_566 . ?
C1 C2 H21 109.5 . . ?
C1 C2 H22 109.5 . . ?
H21 C2 H22 109.5 . . ?
C1 C2 H23 109.5 . . ?
H21 C2 H23 109.5 . . ?
H22 C2 H23 109.5 . . ?
F41 B F21 96.9(12) . . ?
F32 B F12 161(2) . . ?
F32 B F22 89.3(17) . . ?
F12 B F22 109.2(11) . . ?
F41 B F31 100.6(10) . . ?
F21 B F31 108.9(10) . . ?
F41 B F11 112.7(6) . . ?
F21 B F11 121.6(6) . . ?
F31 B F11 113.0(6) . . ?
B F32 F42 55.5(8) . . ?
B F42 F32 47.8(8) . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_bf4_150
_database_code_depnum_ccdc_archive 'CCDC 1856381'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 B2 F8 N2'
_chemical_formula_weight         311.83

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.870(4)
_cell_length_b                   9.528(3)
_cell_length_c                   12.575(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1302.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9642
_cell_measurement_theta_min      3.2336
_cell_measurement_theta_max      36.7766

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_method       ω
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            20344
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.240
_diffrn_reflns_theta_max         36.863
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3199
_reflns_number_gt                2487
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0884P)²+0.3099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3199
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1745
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
N N 0.05601(7) 0.50509(8) 0.40785(6) 0.02231(16) Uani 1 1 d . . . . .
H1 H 0.093080 0.508460 0.345694 0.041(5) Uiso 1 1 calc R . . . .
C1 C 0.02662(8) 0.62816(9) 0.45328(6) 0.02242(17) Uani 1 1 d . . . . .
C2 C 0.03396(8) 0.37750(9) 0.44867(7) 0.02250(17) Uani 1 1 d . . . . .
C11 C 0.05973(11) 0.76190(11) 0.39982(8) 0.0318(2) Uani 1 1 d . . . . .
H111 H 0.103722 0.741550 0.333571 0.048 Uiso 1 1 calc R U . . .
H112 H 0.112606 0.817523 0.446811 0.048 Uiso 1 1 calc R U . . .
H113 H -0.015296 0.814878 0.383816 0.048 Uiso 1 1 calc R U . . .
C21 C 0.07470(11) 0.25019(11) 0.39037(9) 0.0326(2) Uani 1 1 d . . . . .
H211 H 0.121021 0.278109 0.326948 0.049 Uiso 1 1 calc R U . . .
H212 H 0.002609 0.195204 0.369055 0.049 Uiso 1 1 calc R U . . .
H213 H 0.127347 0.193249 0.436637 0.049 Uiso 1 1 calc R U . . .
B B 0.24842(10) 0.53447(13) 0.15899(9) 0.0271(2) Uani 1 1 d . . . . .
F1 F 0.24743(9) 0.47500(10) 0.05935(6) 0.0456(2) Uani 1 1 d . . . . .
F2 F 0.13181(7) 0.51001(9) 0.20633(6) 0.0390(2) Uani 1 1 d . . . . .
F3 F 0.33782(9) 0.47632(12) 0.22220(8) 0.0568(3) Uani 1 1 d . . . . .
F4 F 0.26684(11) 0.67574(10) 0.15001(9) 0.0663(3) 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
N C2 1.3412(12) . ?
N C1 1.3429(12) . ?
C1 C2 1.3988(14) 5_566 ?
C1 C11 1.4850(13) . ?
C2 C21 1.4848(14) . ?
B F4 1.3655(15) . ?
B F3 1.3723(15) . ?
B F1 1.3752(15) . ?
B F2 1.4198(13) . ?

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
C2 N C1 125.89(9) . . ?
N C1 C2 116.95(8) . 5_566 ?
N C1 C11 119.94(8) . . ?
C2 C1 C11 123.10(8) 5_566 . ?
N C2 C1 117.15(8) . 5_566 ?
N C2 C21 119.88(9) . . ?
C1 C2 C21 122.96(8) 5_566 . ?
F4 B F3 110.01(11) . . ?
F4 B F1 109.39(10) . . ?
F3 B F1 111.53(11) . . ?
F4 B F2 109.11(10) . . ?
F3 B F2 108.85(9) . . ?
F1 B F2 107.90(9) . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.072

