# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_d1471_a
_database_code_depnum_ccdc_archive 'CCDC 1522318'
_audit_update_record             
;
2016-12-12 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 B F2 N3 O2'
_chemical_formula_sum            'C19 H22 B F2 N3 O2'
_chemical_formula_weight         373.20

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'
O O 0.0106 0.0060 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   21.7917(19)
_cell_length_b                   11.2285(10)
_cell_length_c                   7.3897(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1808.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    2083
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      21.90

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11348
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4098
_reflns_number_gt                2437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.995

_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0474P)²] 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_abs_structure_details 
; 
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
#_refine_ls_abs_structure_Flack    0.3(6) 
_chemical_absolute_configuration .
_refine_ls_number_reflns         4098
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.15410(11) 0.7797(2) 0.2352(3) 0.0377(7) Uani 1 1 d . . . . .
F2 F 0.13781(11) 0.83905(19) 0.5240(4) 0.0395(7) Uani 1 1 d . . . . .
O1 O 0.07863(14) 0.2629(2) 0.5667(5) 0.0382(8) Uani 1 1 d . . . . .
O2 O 0.42083(14) 0.9973(3) 0.5556(6) 0.0496(10) Uani 1 1 d . . . . .
N1 N 0.16467(14) 0.6344(3) 0.4707(4) 0.0204(8) Uani 1 1 d . . . . .
N2 N 0.24072(14) 0.7954(3) 0.4350(4) 0.0187(8) Uani 1 1 d . . . . .
N3 N 0.42400(14) 0.4637(3) 0.3181(4) 0.0218(8) Uani 1 1 d . . . . .
C1 C 0.11031(18) 0.5779(3) 0.4891(6) 0.0236(10) Uani 1 1 d . . . . .
C2 C 0.12126(18) 0.4550(3) 0.5060(6) 0.0225(10) Uani 1 1 d . . . . .
C3 C 0.18532(18) 0.4363(3) 0.4870(5) 0.0214(9) Uani 1 1 d . . . . .
C4 C 0.21192(17) 0.5493(3) 0.4679(5) 0.0181(9) Uani 1 1 d . . . . .
C5 C 0.27446(18) 0.5868(3) 0.4505(5) 0.0197(9) Uani 1 1 d . . . . .
C6 C 0.28778(17) 0.7123(3) 0.4626(5) 0.0193(9) Uani 1 1 d . . . . .
C7 C 0.34151(17) 0.7743(3) 0.5074(5) 0.0204(9) Uani 1 1 d . . . . .
C8 C 0.32685(18) 0.8974(3) 0.4951(6) 0.0232(10) Uani 1 1 d . . . . .
C9 C 0.26478(19) 0.9062(3) 0.4506(6) 0.0226(9) Uani 1 1 d . . . . .
C10 C 0.04988(18) 0.6410(3) 0.4788(7) 0.0335(11) Uani 1 1 d . . . . .
H10A H 0.0456 0.6786 0.3597 0.050 Uiso 1 1 calc R U . . .
H10B H 0.0480 0.7022 0.5731 0.050 Uiso 1 1 calc R U . . .
H10C H 0.0165 0.5836 0.4967 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0729(2) 0.3700(4) 0.5423(7) 0.0327(11) Uani 1 1 d . . . . .
H11A H 0.0324 0.4007 0.5477 0.039 Uiso 1 1 calc R U . . .
C12 C 0.21514(18) 0.3166(3) 0.4785(7) 0.0284(10) Uani 1 1 d . . . . .
H12A H 0.2449 0.3092 0.5773 0.043 Uiso 1 1 calc R U . . .
H12B H 0.2362 0.3076 0.3622 0.043 Uiso 1 1 calc R U . . .
H12C H 0.1838 0.2545 0.4906 0.043 Uiso 1 1 calc R U . . .
C13 C 0.40100(18) 0.7283(4) 0.5820(7) 0.0300(11) Uani 1 1 d . . . . .
H13A H 0.3949 0.6475 0.6292 0.045 Uiso 1 1 calc R U . . .
H13B H 0.4150 0.7805 0.6798 0.045 Uiso 1 1 calc R U . . .
H13C H 0.4319 0.7266 0.4857 0.045 Uiso 1 1 calc R U . . .
C14 C 0.3661(2) 0.9994(4) 0.5225(6) 0.0351(12) Uani 1 1 d . . . . .
H14A H 0.3474 1.0756 0.5140 0.042 Uiso 1 1 calc R U . . .
C15 C 0.22747(19) 1.0167(3) 0.4220(6) 0.0286(11) Uani 1 1 d . . . . .
H15A H 0.1936 0.9995 0.3386 0.043 Uiso 1 1 calc R U . . .
H15B H 0.2535 1.0792 0.3705 0.043 Uiso 1 1 calc R U . . .
H15C H 0.2108 1.0437 0.5382 0.043 Uiso 1 1 calc R U . . .
C16 C 0.32167(17) 0.5040(3) 0.4241(5) 0.0193(9) Uani 1 1 d . . . . .
H16A H 0.3166 0.4251 0.4682 0.023 Uiso 1 1 calc R U . . .
C17 C 0.37565(17) 0.5340(3) 0.3352(5) 0.0192(9) Uani 1 1 d . . . . .
H17A H 0.3780 0.6110 0.2826 0.023 Uiso 1 1 calc R U . . .
C18 C 0.47346(19) 0.4943(4) 0.1919(6) 0.0297(11) Uani 1 1 d . . . . .
H18A H 0.4671 0.5752 0.1460 0.045 Uiso 1 1 calc R U . . .
H18B H 0.4734 0.4380 0.0906 0.045 Uiso 1 1 calc R U . . .
H18C H 0.5130 0.4901 0.2549 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4266(2) 0.3457(4) 0.4012(6) 0.0298(11) Uani 1 1 d . . . . .
H19A H 0.4118 0.3505 0.5262 0.045 Uiso 1 1 calc R U . . .
H19B H 0.4691 0.3170 0.4008 0.045 Uiso 1 1 calc R U . . .
H19C H 0.4007 0.2905 0.3325 0.045 Uiso 1 1 calc R U . . .
B1 B 0.1725(2) 0.7652(4) 0.4147(7) 0.0224(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 1.395(5) . ?
F2 B1 1.383(5) . ?
O1 C11 1.222(5) . ?
O2 C14 1.217(5) . ?
N1 C1 1.351(5) . ?
N1 C4 1.405(5) . ?
N1 B1 1.535(5) . ?
N2 C9 1.355(5) . ?
N2 C6 1.402(5) . ?
N2 B1 1.533(6) . ?
N3 C17 1.322(4) . ?
N3 C19 1.462(5) . ?
N3 C18 1.466(5) . ?
C1 C2 1.406(5) . ?
C1 C10 1.498(5) . ?
C2 C3 1.419(5) . ?
C2 C11 1.446(6) . ?
C3 C4 1.402(5) . ?
C3 C12 1.494(5) . ?
C4 C5 1.432(5) . ?
C5 C16 1.400(5) . ?
C5 C6 1.441(5) . ?
C6 C7 1.402(5) . ?
C7 C8 1.421(5) . ?
C7 C13 1.501(5) . ?
C8 C9 1.396(6) . ?
C8 C14 1.445(5) . ?
C9 C15 1.499(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.389(5) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 N1 C4 108.9(3) . . ?
C1 N1 B1 125.0(3) . . ?
C4 N1 B1 124.4(3) . . ?
C9 N2 C6 108.4(3) . . ?
C9 N2 B1 125.9(3) . . ?
C6 N2 B1 125.2(3) . . ?
C17 N3 C19 122.1(3) . . ?
C17 N3 C18 120.4(3) . . ?
C19 N3 C18 116.8(3) . . ?
N1 C1 C2 108.8(3) . . ?
N1 C1 C10 122.9(3) . . ?
C2 C1 C10 128.2(4) . . ?
C1 C2 C3 107.7(3) . . ?
C1 C2 C11 122.7(4) . . ?
C3 C2 C11 129.6(3) . . ?
C4 C3 C2 106.4(3) . . ?
C4 C3 C12 129.1(3) . . ?
C2 C3 C12 124.4(3) . . ?
C3 C4 N1 108.1(3) . . ?
C3 C4 C5 131.9(3) . . ?
N1 C4 C5 119.9(3) . . ?
C16 C5 C4 121.1(3) . . ?
C16 C5 C6 120.7(4) . . ?
C4 C5 C6 118.2(3) . . ?
N2 C6 C7 108.3(3) . . ?
N2 C6 C5 119.6(3) . . ?
C7 C6 C5 132.0(4) . . ?
C6 C7 C8 106.3(3) . . ?
C6 C7 C13 129.5(3) . . ?
C8 C7 C13 123.6(3) . . ?
C9 C8 C7 107.6(3) . . ?
C9 C8 C14 123.4(4) . . ?
C7 C8 C14 129.0(4) . . ?
N2 C9 C8 109.2(3) . . ?
N2 C9 C15 122.6(4) . . ?
C8 C9 C15 128.2(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C2 127.1(4) . . ?
O1 C11 H11A 116.5 . . ?
C2 C11 H11A 116.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C8 126.4(4) . . ?
O2 C14 H14A 116.8 . . ?
C8 C14 H14A 116.8 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 121.8(4) . . ?
C17 C16 H16A 119.1 . . ?
C5 C16 H16A 119.1 . . ?
N3 C17 C16 125.1(4) . . ?
N3 C17 H17A 117.4 . . ?
C16 C17 H17A 117.4 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F2 B1 F1 109.2(4) . . ?
F2 B1 N2 109.9(3) . . ?
F1 B1 N2 110.2(3) . . ?
F2 B1 N1 110.8(4) . . ?
F1 B1 N1 109.6(4) . . ?
N2 B1 N1 107.0(3) . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d1594
_database_code_depnum_ccdc_archive 'CCDC 1522319'
_audit_update_record             
;
2016-12-12 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 B F2 N2 O'
_chemical_formula_sum            'C21 H27 B F2 N2 O'
_chemical_formula_weight         372.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5314(8)
_cell_length_b                   10.7672(9)
_cell_length_c                   21.276(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.381(7)
_cell_angle_gamma                90
_cell_volume                     1942.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    2666
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      63.35

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.5582
_exptl_transmission_factor_max   0.7529
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.740
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19300
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.182
_diffrn_reflns_theta_max         67.328
_diffrn_reflns_theta_full        67.328
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3449
_reflns_number_gt                2326
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0436P)²+0.5654P] 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         3449
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.25846(17) 0.49787(12) 0.31588(7) 0.0439(4) Uani 1 1 d . . . . .
F2 F 0.03784(17) 0.60565(11) 0.33219(7) 0.0419(4) Uani 1 1 d . . . . .
O1 O 0.6989(2) 0.96967(15) 0.55462(9) 0.0405(4) Uani 1 1 d . . . . .
N1 N 0.0452(2) 0.38690(16) 0.35467(10) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.2077(2) 0.53415(16) 0.42329(9) 0.0287(4) Uani 1 1 d . . . . .
C1 C 0.1003(3) 0.34746(19) 0.46731(12) 0.0316(6) Uani 1 1 d . . . . .
C2 C 0.0295(3) 0.31248(19) 0.40752(12) 0.0319(6) Uani 1 1 d . . . . .
C3 C -0.0606(3) 0.2050(2) 0.38573(13) 0.0354(6) Uani 1 1 d . . . . .
C4 C -0.0958(3) 0.2192(2) 0.32153(13) 0.0377(6) Uani 1 1 d . . . . .
H4A H -0.1554 0.1626 0.2942 0.045 Uiso 1 1 calc R U . . .
C5 C -0.0290(3) 0.3310(2) 0.30285(13) 0.0348(6) Uani 1 1 d . . . . .
C6 C 0.3001(3) 0.63195(19) 0.44260(12) 0.0293(5) Uani 1 1 d . . . . .
C7 C 0.3499(3) 0.61992(19) 0.50767(11) 0.0296(5) Uani 1 1 d . . . . .
C8 C 0.2822(3) 0.5097(2) 0.52833(12) 0.0317(5) Uani 1 1 d . . . . .
C9 C 0.1927(3) 0.45703(19) 0.47534(12) 0.0300(5) Uani 1 1 d . . . . .
C10 C 0.0803(3) 0.2666(2) 0.52330(13) 0.0404(6) Uani 1 1 d . . . . .
H10A H 0.0735 0.3188 0.5606 0.061 Uiso 1 1 calc R U . . .
H10B H 0.1709 0.2106 0.5310 0.061 Uiso 1 1 calc R U . . .
H10C H -0.0165 0.2177 0.5148 0.061 Uiso 1 1 calc R U . . .
C11 C -0.1031(3) 0.0922(2) 0.42124(14) 0.0442(7) Uani 1 1 d . . . . .
H11A H -0.0074 0.0559 0.4436 0.066 Uiso 1 1 calc R U . . .
H11B H -0.1542 0.0312 0.3915 0.066 Uiso 1 1 calc R U . . .
H11C H -0.1757 0.1156 0.4519 0.066 Uiso 1 1 calc R U . . .
C12 C -0.0314(3) 0.3828(2) 0.23863(13) 0.0444(7) Uani 1 1 d . . . . .
H12A H -0.1046 0.3348 0.2093 0.067 Uiso 1 1 calc R U . . .
H12B H 0.0748 0.3784 0.2252 0.067 Uiso 1 1 calc R U . . .
H12C H -0.0658 0.4696 0.2387 0.067 Uiso 1 1 calc R U . . .
C13 C 0.3354(3) 0.7331(2) 0.39856(12) 0.0350(6) Uani 1 1 d . . . . .
H13A H 0.4492 0.7489 0.4030 0.052 Uiso 1 1 calc R U . . .
H13B H 0.2798 0.8089 0.4087 0.052 Uiso 1 1 calc R U . . .
H13C H 0.3004 0.7082 0.3550 0.052 Uiso 1 1 calc R U . . .
C14 C 0.3057(3) 0.4635(2) 0.59466(13) 0.0413(6) Uani 1 1 d . . . . .
H14A H 0.3952 0.5068 0.6178 0.062 Uiso 1 1 calc R U . . .
H14B H 0.3270 0.3741 0.5946 0.062 Uiso 1 1 calc R U . . .
H14C H 0.2103 0.4792 0.6152 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4577(3) 0.6993(2) 0.54678(12) 0.0315(5) Uani 1 1 d . . . . .
H15A H 0.4925 0.6679 0.5877 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5153(3) 0.8111(2) 0.53325(12) 0.0347(6) Uani 1 1 d . . . . .
H16A H 0.4782 0.8482 0.4939 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6321(3) 0.8793(2) 0.57576(12) 0.0319(6) Uani 1 1 d . . . . .
C18 C 0.6669(3) 0.8422(2) 0.64376(12) 0.0344(6) Uani 1 1 d . . . . .
H18A H 0.7632 0.8862 0.6621 0.041 Uiso 1 1 calc R U . . .
H18B H 0.6895 0.7521 0.6458 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5343(3) 0.8698(2) 0.68417(13) 0.0373(6) Uani 1 1 d . . . . .
H19A H 0.4398 0.8202 0.6672 0.045 Uiso 1 1 calc R U . . .
C20 C 0.4885(3) 1.0061(2) 0.68216(15) 0.0516(8) Uani 1 1 d . . . . .
H20A H 0.4028 1.0196 0.7085 0.077 Uiso 1 1 calc R U . . .
H20B H 0.4531 1.0302 0.6384 0.077 Uiso 1 1 calc R U . . .
H20C H 0.5799 1.0566 0.6982 0.077 Uiso 1 1 calc R U . . .
C21 C 0.5837(4) 0.8283(3) 0.75170(15) 0.0605(8) Uani 1 1 d . . . . .
H21A H 0.4972 0.8433 0.7774 0.091 Uiso 1 1 calc R U . . .
H21B H 0.6769 0.8753 0.7691 0.091 Uiso 1 1 calc R U . . .
H21C H 0.6088 0.7395 0.7521 0.091 Uiso 1 1 calc R U . . .
B1 B 0.1386(3) 0.5092(2) 0.35461(14) 0.0317(6) 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 1.388(3) . ?
F2 B1 1.397(3) . ?
O1 C17 1.237(3) . ?
N1 C5 1.350(3) . ?
N1 C2 1.399(3) . ?
N1 B1 1.540(3) . ?
N2 C6 1.352(3) . ?
N2 C9 1.401(3) . ?
N2 B1 1.537(3) . ?
C1 C2 1.398(3) . ?
C1 C9 1.419(3) . ?
C1 C10 1.500(3) . ?
C2 C3 1.438(3) . ?
C3 C4 1.374(4) . ?
C3 C11 1.496(3) . ?
C4 C5 1.408(3) . ?
C4 H4A 0.9500 . ?
C5 C12 1.474(4) . ?
C6 C7 1.408(3) . ?
C6 C13 1.489(3) . ?
C7 C8 1.411(3) . ?
C7 C15 1.449(3) . ?
C8 C9 1.409(3) . ?
C8 C14 1.489(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.344(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.466(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.498(3) . ?
C18 C19 1.524(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.518(3) . ?
C19 C21 1.519(4) . ?
C19 H19A 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C5 N1 C2 108.84(18) . . ?
C5 N1 B1 125.2(2) . . ?
C2 N1 B1 125.9(2) . . ?
C6 N2 C9 108.82(19) . . ?
C6 N2 B1 125.03(19) . . ?
C9 N2 B1 126.07(18) . . ?
C2 C1 C9 120.8(2) . . ?
C2 C1 C10 119.4(2) . . ?
C9 C1 C10 119.8(2) . . ?
C1 C2 N1 120.45(19) . . ?
C1 C2 C3 132.2(2) . . ?
N1 C2 C3 107.3(2) . . ?
C4 C3 C2 106.3(2) . . ?
C4 C3 C11 123.6(2) . . ?
C2 C3 C11 129.9(2) . . ?
C3 C4 C5 109.0(2) . . ?
C3 C4 H4A 125.5 . . ?
C5 C4 H4A 125.5 . . ?
N1 C5 C4 108.6(2) . . ?
N1 C5 C12 123.0(2) . . ?
C4 C5 C12 128.4(2) . . ?
N2 C6 C7 109.2(2) . . ?
N2 C6 C13 122.0(2) . . ?
C7 C6 C13 128.7(2) . . ?
C6 C7 C8 107.1(2) . . ?
C6 C7 C15 127.8(2) . . ?
C8 C7 C15 124.9(2) . . ?
C9 C8 C7 107.1(2) . . ?
C9 C8 C14 128.9(2) . . ?
C7 C8 C14 124.0(2) . . ?
N2 C9 C8 107.76(19) . . ?
N2 C9 C1 119.7(2) . . ?
C8 C9 C1 132.5(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C7 129.0(2) . . ?
C16 C15 H15A 115.5 . . ?
C7 C15 H15A 115.5 . . ?
C15 C16 C17 123.8(2) . . ?
C15 C16 H16A 118.1 . . ?
C17 C16 H16A 118.1 . . ?
O1 C17 C16 118.6(2) . . ?
O1 C17 C18 120.7(2) . . ?
C16 C17 C18 120.7(2) . . ?
C17 C18 C19 114.4(2) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C21 110.8(2) . . ?
C20 C19 C18 112.2(2) . . ?
C21 C19 C18 109.3(2) . . ?
C20 C19 H19A 108.1 . . ?
C21 C19 H19A 108.1 . . ?
C18 C19 H19A 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1 B1 F2 109.2(2) . . ?
F1 B1 N2 110.5(2) . . ?
F2 B1 N2 110.56(19) . . ?
F1 B1 N1 109.92(19) . . ?
F2 B1 N1 109.7(2) . . ?
N2 B1 N1 106.99(19) . . ?

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 C1 C2 N1 -1.7(3) . . . . ?
C10 C1 C2 N1 179.4(2) . . . . ?
C9 C1 C2 C3 175.9(2) . . . . ?
C10 C1 C2 C3 -3.0(4) . . . . ?
C5 N1 C2 C1 178.0(2) . . . . ?
B1 N1 C2 C1 0.9(3) . . . . ?
C5 N1 C2 C3 -0.2(2) . . . . ?
B1 N1 C2 C3 -177.3(2) . . . . ?
C1 C2 C3 C4 -178.1(2) . . . . ?
N1 C2 C3 C4 -0.3(2) . . . . ?
C1 C2 C3 C11 -2.3(4) . . . . ?
N1 C2 C3 C11 175.6(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C11 C3 C4 C5 -175.6(2) . . . . ?
C2 N1 C5 C4 0.6(3) . . . . ?
B1 N1 C5 C4 177.7(2) . . . . ?
C2 N1 C5 C12 -178.1(2) . . . . ?
B1 N1 C5 C12 -1.0(4) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C3 C4 C5 C12 177.8(2) . . . . ?
C9 N2 C6 C7 1.0(2) . . . . ?
B1 N2 C6 C7 -176.0(2) . . . . ?
C9 N2 C6 C13 -178.3(2) . . . . ?
B1 N2 C6 C13 4.7(3) . . . . ?
N2 C6 C7 C8 -0.6(2) . . . . ?
C13 C6 C7 C8 178.6(2) . . . . ?
N2 C6 C7 C15 175.9(2) . . . . ?
C13 C6 C7 C15 -4.9(4) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C15 C7 C8 C9 -176.6(2) . . . . ?
C6 C7 C8 C14 -179.8(2) . . . . ?
C15 C7 C8 C14 3.6(4) . . . . ?
C6 N2 C9 C8 -0.9(2) . . . . ?
B1 N2 C9 C8 176.0(2) . . . . ?
C6 N2 C9 C1 179.8(2) . . . . ?
B1 N2 C9 C1 -3.2(3) . . . . ?
C7 C8 C9 N2 0.5(2) . . . . ?
C14 C8 C9 N2 -179.6(2) . . . . ?
C7 C8 C9 C1 179.7(2) . . . . ?
C14 C8 C9 C1 -0.5(4) . . . . ?
C2 C1 C9 N2 2.8(3) . . . . ?
C10 C1 C9 N2 -178.3(2) . . . . ?
C2 C1 C9 C8 -176.2(2) . . . . ?
C10 C1 C9 C8 2.7(4) . . . . ?
C6 C7 C15 C16 11.4(4) . . . . ?
C8 C7 C15 C16 -172.7(2) . . . . ?
C7 C15 C16 C17 -176.1(2) . . . . ?
C15 C16 C17 O1 166.9(2) . . . . ?
C15 C16 C17 C18 -14.6(3) . . . . ?
O1 C17 C18 C19 107.9(3) . . . . ?
C16 C17 C18 C19 -70.5(3) . . . . ?
C17 C18 C19 C20 -56.7(3) . . . . ?
C17 C18 C19 C21 -180.0(2) . . . . ?
C6 N2 B1 F1 59.0(3) . . . . ?
C9 N2 B1 F1 -117.4(2) . . . . ?
C6 N2 B1 F2 -61.9(3) . . . . ?
C9 N2 B1 F2 121.6(2) . . . . ?
C6 N2 B1 N1 178.66(19) . . . . ?
C9 N2 B1 N1 2.2(3) . . . . ?
C5 N1 B1 F1 -57.7(3) . . . . ?
C2 N1 B1 F1 119.0(2) . . . . ?
C5 N1 B1 F2 62.4(3) . . . . ?
C2 N1 B1 F2 -120.9(2) . . . . ?
C5 N1 B1 N2 -177.6(2) . . . . ?
C2 N1 B1 N2 -1.0(3) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.046

