# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_er20170215_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1892765'
loop_
_audit_author_name
_audit_author_address
'Etienne Rochette '
;Universit? Laval 
Canada
;
_audit_update_record             
;
2019-01-31 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_date             2018-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            3-Et
_chemical_name_systematic        3-Et
_chemical_formula_moiety         'C12 H17 B F3 N'
_chemical_formula_sum            'C12 H17 B F3 N'
_chemical_formula_weight         243.07
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1685(7)
_cell_length_b                   14.6515(13)
_cell_length_c                   10.9025(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.1760(10)
_cell_angle_gamma                90
_cell_volume                     1239.71(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5681
_cell_measurement_temperature    150
_cell_measurement_theta_max      2.4080
_cell_measurement_theta_min      31.4699
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0488 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.9364.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_preparation       'Trfiluoroborate method'
_exptl_crystal_recrystallization_method 'Slow evaporation in acetone'
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17578
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.456
_diffrn_reflns_theta_min         1.966
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       Monocrystal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          .
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                7009
_reflns_number_total             8561
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 2742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         8561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.040
_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)+(0.0870P)²+0.0685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1481
_refine_special_details          
'BF3 moieities were refined usins SIMU commands. H atoms refined using riding model or Free refining.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of C9, {H11A,H11B} of C11, {H21A,H21B} of C21,
  {H23A,H23B} of C23, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H22A,H22B} of C22, {H24A,H24B} of C24
2. Uiso/Uaniso restraints and constraints
F1 \\sim F3 \\sim F2: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
F6 \\sim F5 \\sim F4: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
3.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A), C6(H6), C7(H7), C16(H16), C13(H13), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
N1 N 0.9435(2) 0.02439(14) 0.63308(18) 0.0230(4) Uani 1 1 d . . . . .
H1 H 1.0721 0.0236 0.6576 0.028 Uiso 1 1 calc R . . . .
F2 F 1.2739(2) 0.04336(14) 0.7999(2) 0.0474(5) Uani 1 1 d . U . . .
F1 F 1.2908(2) -0.10690(13) 0.8571(2) 0.0423(4) Uani 1 1 d . U . . .
F3 F 1.3273(2) 0.00296(15) 1.01049(17) 0.0453(4) Uani 1 1 d . U . . .
C5 C 0.8000(3) -0.04556(15) 0.9651(2) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.9748(3) -0.04410(16) 0.9709(2) 0.0235(4) Uani 1 1 d . . . . .
H4 H 1.0597 -0.0594 1.0500 0.028 Uiso 1 1 calc R . . . .
C3 C 1.0287(3) -0.02100(14) 0.8646(2) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.8980(3) 0.00093(14) 0.7509(2) 0.0208(4) Uani 1 1 d . . . . .
C1 C 0.7246(3) 0.00168(17) 0.7420(2) 0.0256(4) Uani 1 1 d . . . . .
H1A H 0.6397 0.0177 0.6632 0.031 Uiso 1 1 calc R . . . .
C6 C 0.6765(3) -0.02130(17) 0.8496(2) 0.0261(4) Uani 1 1 d . . . . .
H6 H 0.5582 -0.0205 0.8443 0.031 Uiso 1 1 calc R . . . .
C7 C 0.7413(3) -0.07539(17) 1.0739(3) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.6203 -0.0777 1.0589 0.035 Uiso 1 1 calc R . . . .
C11 C 0.8850(3) 0.11941(17) 0.5820(2) 0.0282(5) Uani 1 1 d . . . . .
H11A H 0.9230 0.1317 0.5059 0.034 Uiso 1 1 calc R . . . .
H11B H 0.7575 0.1220 0.5538 0.034 Uiso 1 1 calc R . . . .
C12 C 0.9563(4) 0.19201(18) 0.6824(3) 0.0336(5) Uani 1 1 d . . . . .
H12A H 0.9157 0.2521 0.6459 0.050 Uiso 1 1 calc GR . . . .
H12B H 1.0824 0.1905 0.7093 0.050 Uiso 1 1 calc GR . . . .
H12C H 0.9170 0.1807 0.7573 0.050 Uiso 1 1 calc GR . . . .
C9 C 0.8772(4) -0.0452(2) 0.5266(3) 0.0342(5) Uani 1 1 d . . . . .
H9A H 0.7506 -0.0506 0.5055 0.041 Uiso 1 1 calc R . . . .
H9B H 0.9024 -0.0240 0.4482 0.041 Uiso 1 1 calc R . . . .
B1 B 1.2336(3) -0.0214(2) 0.8835(3) 0.0277(5) Uani 1 1 d . . . . .
C8 C 0.8404(4) -0.0991(2) 1.1896(3) 0.0399(6) Uani 1 1 d . . . . .
C10 C 0.9579(5) -0.1369(2) 0.5650(3) 0.0443(7) Uani 1 1 d . . . . .
H10A H 0.9085 -0.1808 0.4954 0.066 Uiso 1 1 calc GR . . . .
H10B H 0.9355 -0.1574 0.6438 0.066 Uiso 1 1 calc GR . . . .
H10C H 1.0825 -0.1325 0.5808 0.066 Uiso 1 1 calc GR . . . .
F5 F 0.2810(3) 0.01406(11) 0.31345(18) 0.0418(4) Uani 1 1 d . U . . .
N2 N 0.3415(3) 0.18363(14) 0.22199(19) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.3133 0.1171 0.2188 0.031 Uiso 1 1 calc R . . . .
F4 F 0.2427(3) 0.01282(12) 0.51511(17) 0.0423(4) Uani 1 1 d . U . . .
F6 F 0.0626(2) 0.09452(14) 0.35055(19) 0.0444(4) Uani 1 1 d . U . . .
C16 C 0.4172(3) 0.18583(17) 0.5780(2) 0.0269(4) Uani 1 1 d . . . . .
H16 H 0.3884 0.1507 0.6415 0.032 Uiso 1 1 calc R . . . .
C15 C 0.3605(3) 0.15546(15) 0.4493(2) 0.0240(4) Uani 1 1 d . . . . .
C14 C 0.4082(3) 0.20958(15) 0.3609(2) 0.0231(4) Uani 1 1 d . . . . .
C13 C 0.5035(3) 0.28960(17) 0.3947(3) 0.0292(5) Uani 1 1 d . . . . .
H13 H 0.5320 0.3248 0.3310 0.035 Uiso 1 1 calc R . . . .
C18 C 0.5563(3) 0.31720(17) 0.5231(3) 0.0318(5) Uani 1 1 d . . . . .
H18 H 0.6215 0.3717 0.5471 0.038 Uiso 1 1 calc R . . . .
C17 C 0.5149(3) 0.26601(18) 0.6171(3) 0.0296(5) Uani 1 1 d . . . . .
C23 C 0.4670(4) 0.1965(2) 0.1479(3) 0.0334(5) Uani 1 1 d . . . . .
H23A H 0.4137 0.1750 0.0582 0.040 Uiso 1 1 calc R . . . .
H23B H 0.4925 0.2623 0.1447 0.040 Uiso 1 1 calc R . . . .
C19 C 0.5747(4) 0.2981(2) 0.7516(3) 0.0373(6) Uani 1 1 d . . . . .
H19 H 0.6200 0.3583 0.7659 0.045 Uiso 1 1 calc R . . . .
C21 C 0.1712(3) 0.23460(17) 0.1635(3) 0.0306(5) Uani 1 1 d . . . . .
H21A H 0.079(5) 0.215(3) 0.198(3) 0.037 Uiso 1 1 d R . . . .
H21B H 0.199(5) 0.300(3) 0.166(3) 0.037 Uiso 1 1 d R . . . .
B2 B 0.2366(4) 0.06695(19) 0.4086(3) 0.0300(6) Uani 1 1 d . . . . .
C22 C 0.0759(5) 0.2039(3) 0.0287(3) 0.0452(7) Uani 1 1 d . . . . .
H22A H 0.136(6) 0.215(4) -0.041(5) 0.068 Uiso 1 1 d R . . . .
H22B H 0.048(6) 0.141(4) 0.026(5) 0.068 Uiso 1 1 d R . . . .
C20 C 0.5714(5) 0.2513(3) 0.8547(3) 0.0461(7) Uani 1 1 d . . . . .
C24 C 0.6323(5) 0.1457(3) 0.2073(4) 0.0463(7) Uani 1 1 d . . . . .
H24A H 0.696(7) 0.140(4) 0.164(5) 0.069 Uiso 1 1 d R . . . .
H24B H 0.715(6) 0.172(4) 0.295(5) 0.069 Uiso 1 1 d R . . . .
H8A H 0.958(5) -0.093(3) 1.215(4) 0.041(9) Uiso 1 1 d . . . . .
H20A H 0.618(5) 0.290(3) 0.940(4) 0.039(9) Uiso 1 1 d . . . . .
H8B H 0.775(5) -0.121(3) 1.259(4) 0.055(11) Uiso 1 1 d . . . . .
H20B H 0.541(5) 0.187(3) 0.850(4) 0.043(10) Uiso 1 1 d . . . . .
H24C H 0.626(6) 0.091(4) 0.237(5) 0.066(14) Uiso 1 1 d . . . . .
H22C H -0.039(7) 0.235(4) -0.011(5) 0.067(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.485(3) . ?
N1 C11 1.520(3) . ?
N1 C9 1.512(3) . ?
F2 B1 1.423(3) . ?
F1 B1 1.399(3) . ?
F3 B1 1.403(3) . ?
C5 C4 1.410(3) . ?
C5 C6 1.392(3) . ?
C5 C7 1.478(3) . ?
C4 C3 1.403(3) . ?
C3 C2 1.398(3) . ?
C3 B1 1.621(3) . ?
C2 C1 1.390(3) . ?
C1 C6 1.390(3) . ?
C7 C8 1.316(4) . ?
C11 C12 1.507(4) . ?
C9 C10 1.498(5) . ?
F5 B2 1.429(3) . ?
N2 C14 1.490(3) . ?
N2 C23 1.502(3) . ?
N2 C21 1.531(3) . ?
F4 B2 1.394(3) . ?
F6 B2 1.423(4) . ?
C16 C15 1.405(3) . ?
C16 C17 1.409(4) . ?
C15 C14 1.394(3) . ?
C15 B2 1.619(4) . ?
C14 C13 1.392(3) . ?
C13 C18 1.390(4) . ?
C18 C17 1.394(4) . ?
C17 C19 1.471(4) . ?
C23 C24 1.500(5) . ?
C19 C20 1.324(5) . ?
C21 C22 1.502(4) . ?

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 C11 113.18(18) . . ?
C2 N1 C9 112.42(18) . . ?
C9 N1 C11 109.86(19) . . ?
C4 C5 C7 123.1(2) . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 C7 118.4(2) . . ?
C3 C4 C5 122.8(2) . . ?
C4 C3 B1 118.12(19) . . ?
C2 C3 C4 115.96(18) . . ?
C2 C3 B1 125.92(19) . . ?
C3 C2 N1 119.47(18) . . ?
C1 C2 N1 117.58(19) . . ?
C1 C2 C3 122.9(2) . . ?
C2 C1 C6 119.3(2) . . ?
C1 C6 C5 120.6(2) . . ?
C8 C7 C5 126.2(3) . . ?
C12 C11 N1 112.0(2) . . ?
C10 C9 N1 111.7(2) . . ?
F2 B1 C3 110.63(19) . . ?
F1 B1 F2 107.8(2) . . ?
F1 B1 F3 108.4(2) . . ?
F1 B1 C3 112.0(2) . . ?
F3 B1 F2 107.4(2) . . ?
F3 B1 C3 110.4(2) . . ?
C14 N2 C23 114.80(19) . . ?
C14 N2 C21 107.21(19) . . ?
C23 N2 C21 113.5(2) . . ?
C15 C16 C17 123.1(2) . . ?
C16 C15 B2 120.7(2) . . ?
C14 C15 C16 115.7(2) . . ?
C14 C15 B2 123.5(2) . . ?
C15 C14 N2 117.7(2) . . ?
C13 C14 N2 118.8(2) . . ?
C13 C14 C15 123.3(2) . . ?
C18 C13 C14 119.0(2) . . ?
C13 C18 C17 120.9(2) . . ?
C16 C17 C19 123.3(2) . . ?
C18 C17 C16 118.0(2) . . ?
C18 C17 C19 118.7(2) . . ?
C24 C23 N2 112.3(2) . . ?
C20 C19 C17 126.3(3) . . ?
C22 C21 N2 112.8(2) . . ?
F5 B2 C15 110.8(2) . . ?
F4 B2 F5 110.2(2) . . ?
F4 B2 F6 107.6(2) . . ?
F4 B2 C15 111.8(2) . . ?
F6 B2 F5 106.0(2) . . ?
F6 B2 C15 110.3(2) . . ?

_olex2_exptl_crystal_mounting_method 'Manual '
_olex2_submission_original_sample_id '3-Et '
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT391_er20170215_0m_a     
;
PROBLEM: Deviating Methyl C24       H-C-H Bond Angle ....         95 Degree
RESPONSE: Alkyl chain is free of rotation. Disorder can occur  
;
# end Validation Reply Form

####################################################################### 
# 
# 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_er20161206_0m
_database_code_depnum_ccdc_archive 'CCDC 1892766'
loop_
_audit_author_name
_audit_author_address
'Etienne Rochette '
;Universit? Laval 
Canada
;
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_date             2018-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            3-Me
_chemical_name_systematic        3-Me
_chemical_formula_moiety         '4(C10 H13 B F3 N)'
_chemical_formula_sum            'C40 H52 B4 F12 N4'
_chemical_formula_weight         860.09
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.504(3)
_cell_length_b                   10.4434(19)
_cell_length_c                   7.9038(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.354(3)
_cell_angle_gamma                90
_cell_volume                     1079.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2784
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.8392
_cell_measurement_theta_min      2.4954
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0550 before and 0.0449 after correction. The Ratio of minimum to maximum transmission is 0.9088. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_preparation       'Trifluoroborate method'
_exptl_crystal_recrystallization_method 'Slow evaporation in acetone'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15071
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.173
_diffrn_reflns_theta_min         1.556
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2611
_reflns_number_total             3927
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3927
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.1210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1288
_olex2_refinement_description    
;
1. Rigid bond restraints
 F3A, F3, F1A, F1, F2A, F2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F1A, F1, F3A, F3, F2A, F2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F1A, F1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2A, F2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F3A, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
F1A \\sim F1: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
F3A \\sim F3: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
F2 \\sim F2A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
F2A \\sim F2 \\sim F1 \\sim F1A \\sim F3A \\sim F3: within 3A with sigma of
0.02 and sigma for terminal atoms of 0.04
3. Rigid body (RIGU) restrains
 F3A, F1A, F1, F2A, F2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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 0.8402(4) 0.6145(2) 0.6160(8) 0.0573(11) Uani 0.694(19) 1 d . U P A 1
F2 F 0.8115(2) 0.4276(4) 0.7427(3) 0.0442(7) Uani 0.694(19) 1 d . U P A 1
F3 F 0.9330(4) 0.4296(5) 0.5835(6) 0.0293(6) Uani 0.694(19) 1 d . U P A 1
N1 N 0.86736(7) 0.47387(8) 0.22720(11) 0.02575(19) Uani 1 1 d . . . . .
C1 C 0.56938(9) 0.38768(10) 0.28457(14) 0.0308(2) Uani 1 1 d . . . . .
C2 C 0.59014(9) 0.38793(11) 0.11981(14) 0.0320(2) Uani 1 1 d . . . . .
H2 H 0.5361(10) 0.3696(13) 0.0106(18) 0.040(4) Uiso 1 1 d . . . . .
C3 C 0.68703(9) 0.41528(11) 0.10151(13) 0.0304(2) Uani 1 1 d . . . . .
H3 H 0.7023(10) 0.4137(14) -0.0125(19) 0.045(4) Uiso 1 1 d . . . . .
C4 C 0.76381(8) 0.44415(10) 0.25005(12) 0.0251(2) Uani 1 1 d . . . . .
C5 C 0.74838(8) 0.44642(10) 0.41777(12) 0.0269(2) Uani 1 1 d . . . . .
C6 C 0.64922(9) 0.41648(11) 0.42939(14) 0.0313(2) Uani 1 1 d . . . . .
H6 H 0.6340(10) 0.4163(13) 0.5433(18) 0.039(4) Uiso 1 1 d . . . . .
C7 C 0.46777(9) 0.35845(13) 0.31167(17) 0.0385(3) Uani 1 1 d . . . . .
H7 H 0.4618(11) 0.3700(14) 0.432(2) 0.049(4) Uiso 1 1 d . . . . .
C8 C 0.38625(11) 0.31868(16) 0.1949(2) 0.0489(3) Uani 1 1 d . . . . .
H8A H 0.3881(12) 0.3028(16) 0.073(2) 0.059(5) Uiso 1 1 d . . . . .
H8B H 0.3242(12) 0.2997(16) 0.2289(19) 0.056(4) Uiso 1 1 d . . . . .
C9 C 0.86894(11) 0.59461(13) 0.12659(18) 0.0396(3) Uani 1 1 d . . . . .
H9A H 0.8260(11) 0.5816(14) 0.007(2) 0.048(4) Uiso 1 1 d . . . . .
H9B H 0.9401(12) 0.6122(13) 0.1310(19) 0.042(4) Uiso 1 1 d . . . . .
H9C H 0.8443(11) 0.6614(15) 0.1840(18) 0.044(4) Uiso 1 1 d . . . . .
C10 C 0.91246(10) 0.36376(13) 0.15104(17) 0.0365(3) Uani 1 1 d . . . . .
H10A H 0.9050(12) 0.2873(17) 0.219(2) 0.058(4) Uiso 1 1 d . . . . .
H10B H 0.9841(11) 0.3851(13) 0.1603(18) 0.043(4) Uiso 1 1 d . . . . .
H10C H 0.8727(11) 0.3547(14) 0.033(2) 0.047(4) Uiso 1 1 d . . . . .
B1 B 0.83502(11) 0.48555(14) 0.59060(16) 0.0361(3) Uani 1 1 d . . . . .
F1A F 0.8715(11) 0.6234(7) 0.5606(17) 0.060(2) Uani 0.306(19) 1 d . U P A 2
F2A F 0.8159(6) 0.485(3) 0.7379(9) 0.075(3) Uani 0.306(19) 1 d . U P A 2
F3A F 0.9290(10) 0.4429(13) 0.5951(15) 0.048(3) Uani 0.306(19) 1 d . U P A 2
H1 H 0.9083(10) 0.4883(13) 0.3322(18) 0.038(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.361(3) . ?
F2 B1 1.450(3) . ?
F3 B1 1.461(6) . ?
N1 C4 1.4865(14) . ?
N1 C9 1.4938(15) . ?
N1 C10 1.4957(15) . ?
N1 H1 0.888(14) . ?
C1 C2 1.3984(15) . ?
C1 C6 1.3969(15) . ?
C1 C7 1.4723(17) . ?
C2 H2 1.001(13) . ?
C2 C3 1.3814(17) . ?
C3 H3 0.973(15) . ?
C3 C4 1.3932(14) . ?
C4 C5 1.3923(14) . ?
C5 C6 1.4001(16) . ?
C5 B1 1.6154(16) . ?
C6 H6 0.972(14) . ?
C7 H7 0.978(16) . ?
C7 C8 1.316(2) . ?
C8 H8A 0.987(16) . ?
C8 H8B 0.963(16) . ?
C9 H9A 0.988(15) . ?
C9 H9B 0.970(15) . ?
C9 H9C 0.937(15) . ?
C10 H10A 0.983(17) . ?
C10 H10B 0.978(14) . ?
C10 H10C 0.956(15) . ?
B1 F1A 1.559(13) . ?
B1 F2A 1.254(8) . ?
B1 F3A 1.337(14) . ?

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
C4 N1 C9 112.27(9) . . ?
C4 N1 C10 112.18(9) . . ?
C4 N1 H1 107.9(9) . . ?
C9 N1 C10 111.95(10) . . ?
C9 N1 H1 105.5(9) . . ?
C10 N1 H1 106.6(9) . . ?
C2 C1 C7 123.03(10) . . ?
C6 C1 C2 118.06(10) . . ?
C6 C1 C7 118.90(10) . . ?
C1 C2 H2 122.1(8) . . ?
C3 C2 C1 120.78(10) . . ?
C3 C2 H2 117.2(8) . . ?
C2 C3 H3 121.1(8) . . ?
C2 C3 C4 118.87(10) . . ?
C4 C3 H3 120.0(8) . . ?
C3 C4 N1 117.96(9) . . ?
C5 C4 N1 118.66(9) . . ?
C5 C4 C3 123.39(10) . . ?
C4 C5 C6 115.47(9) . . ?
C4 C5 B1 124.16(10) . . ?
C6 C5 B1 120.34(10) . . ?
C1 C6 C5 123.43(10) . . ?
C1 C6 H6 117.4(8) . . ?
C5 C6 H6 119.1(8) . . ?
C1 C7 H7 114.8(8) . . ?
C8 C7 C1 127.66(13) . . ?
C8 C7 H7 117.6(8) . . ?
C7 C8 H8A 121.3(10) . . ?
C7 C8 H8B 120.3(9) . . ?
H8A C8 H8B 118.3(13) . . ?
N1 C9 H9A 108.1(9) . . ?
N1 C9 H9B 106.6(8) . . ?
N1 C9 H9C 108.5(9) . . ?
H9A C9 H9B 113.7(12) . . ?
H9A C9 H9C 111.7(12) . . ?
H9B C9 H9C 108.0(12) . . ?
N1 C10 H10A 107.3(9) . . ?
N1 C10 H10B 106.8(8) . . ?
N1 C10 H10C 106.4(9) . . ?
H10A C10 H10B 112.3(12) . . ?
H10A C10 H10C 110.1(13) . . ?
H10B C10 H10C 113.7(12) . . ?
F1 B1 F2 107.7(2) . . ?
F1 B1 F3 112.8(4) . . ?
F1 B1 C5 112.05(15) . . ?
F2 B1 F3 104.58(19) . . ?
F2 B1 C5 109.50(18) . . ?
F3 B1 C5 109.9(2) . . ?
F1A B1 C5 107.2(3) . . ?
F2A B1 C5 120.8(5) . . ?
F2A B1 F1A 106.8(7) . . ?
F2A B1 F3A 112.8(7) . . ?
F3A B1 C5 114.9(6) . . ?
F3A B1 F1A 88.8(8) . . ?

_olex2_exptl_crystal_mounting_method 'Manual '
_olex2_submission_original_sample_id NB3178
_olex2_submission_special_instructions 'No special instructions were received'
