# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_1
_database_code_depnum_ccdc_archive 'CCDC 1523987'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-10 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         ?
_chemical_formula_sum            'C14 H11 B F2 N2 O2'
_chemical_formula_weight         288.06

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'
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'
N N 0.0311 0.0180 '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                   6.2396(2)
_cell_length_b                   15.0244(5)
_cell_length_c                   13.6239(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.777(2)
_cell_angle_gamma                90
_cell_volume                     1222.83(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4711
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      65.12

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    1.066
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6968
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7595
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.489
_diffrn_reflns_theta_max         65.773
_diffrn_reflns_theta_full        65.773
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             2021
_reflns_number_gt                1845
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)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         2021
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1856
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   1.608
_refine_ls_restrained_S_all      1.608
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.009

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 0.08715(19) 0.06092(8) 0.90366(9) 0.0352(4) Uani 1 1 d . . . . .
F2 F 0.0789(2) 0.06504(8) 0.73616(8) 0.0359(4) Uani 1 1 d . . . . .
O1 O 0.1355(2) -0.07009(9) 0.82433(10) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.8775(2) 0.24488(9) 0.91640(10) 0.0294(4) Uani 1 1 d . . . . .
H2 H 0.8177 0.1943 0.9091 0.044 Uiso 1 1 d R U . . .
N1 N 0.4392(3) 0.04516(11) 0.86316(11) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.5345(3) 0.13038(11) 0.87390(11) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.2947(3) -0.13303(14) 0.84656(13) 0.0260(5) Uani 1 1 d . . . . .
C2 C 0.2339(4) -0.22254(14) 0.84067(14) 0.0288(5) Uani 1 1 d . . . . .
H2A H 0.0835 -0.2385 0.8219 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3965(3) -0.28708(14) 0.86269(14) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.3549 -0.3467 0.8587 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6255(3) -0.26462(14) 0.89125(14) 0.0291(5) Uani 1 1 d . . . . .
H4A H 0.7342 -0.3089 0.9060 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6858(3) -0.17688(13) 0.89694(13) 0.0273(5) Uani 1 1 d . . . . .
H5 H 0.8366 -0.1616 0.9157 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5227(3) -0.10954(13) 0.87476(13) 0.0246(5) Uani 1 1 d . . . . .
C7 C 0.5849(3) -0.01845(13) 0.88100(12) 0.0241(5) Uani 1 1 d . . . . .
H7 H 0.7361 -0.0039 0.8986 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4001(3) 0.19686(13) 0.86233(13) 0.0264(5) Uani 1 1 d . . . . .
H8 H 0.2468 0.1868 0.8464 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4845(3) 0.28754(13) 0.87375(13) 0.0246(5) Uani 1 1 d . . . . .
C10 C 0.7162(3) 0.30834(14) 0.90128(13) 0.0262(5) Uani 1 1 d . . . . .
C11 C 0.7823(3) 0.39697(13) 0.91407(14) 0.0283(5) Uani 1 1 d . . . . .
H11 H 0.9338 0.4111 0.9334 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6264(4) 0.46389(14) 0.89844(14) 0.0294(5) Uani 1 1 d . . . . .
H12 H 0.6733 0.5229 0.9076 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3982(3) 0.44423(13) 0.86896(14) 0.0287(5) Uani 1 1 d . . . . .
H13 H 0.2926 0.4897 0.8572 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3317(3) 0.35654(13) 0.85753(13) 0.0260(5) Uani 1 1 d . . . . .
H14 H 0.1796 0.3433 0.8384 0.031 Uiso 1 1 calc R U . . .
B1 B 0.1727(4) 0.02498(16) 0.82946(16) 0.0297(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 1.382(2) . ?
F2 B1 1.375(3) . ?
O1 C1 1.342(2) . ?
O1 B1 1.446(3) . ?
O2 C10 1.358(2) . ?
O2 H2 0.8400 . ?
N1 C7 1.293(2) . ?
N1 N2 1.401(2) . ?
N1 B1 1.620(3) . ?
N2 C8 1.284(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.409(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.453(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.383(3) . ?
C9 C10 1.420(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 O1 B1 125.97(17) . . ?
C10 O2 H2 109.4 . . ?
C7 N1 N2 113.67(16) . . ?
C7 N1 B1 121.55(17) . . ?
N2 N1 B1 124.77(15) . . ?
C8 N2 N1 117.10(16) . . ?
O1 C1 C2 119.72(18) . . ?
O1 C1 C6 120.62(19) . . ?
C2 C1 C6 119.66(19) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.18(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.16(19) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 120.80(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.38(19) . . ?
C5 C6 C7 120.89(18) . . ?
C1 C6 C7 119.73(18) . . ?
N1 C7 C6 122.45(18) . . ?
N1 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
N2 C8 C9 120.84(18) . . ?
N2 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C14 C9 C10 118.69(18) . . ?
C14 C9 C8 118.29(18) . . ?
C10 C9 C8 123.01(18) . . ?
O2 C10 C11 118.27(17) . . ?
O2 C10 C9 122.61(18) . . ?
C11 C10 C9 119.12(18) . . ?
C12 C11 C10 120.76(19) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.56(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.99(19) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 121.86(18) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
F2 B1 F1 110.71(18) . . ?
F2 B1 O1 111.60(17) . . ?
F1 B1 O1 109.31(17) . . ?
F2 B1 N1 107.97(16) . . ?
F1 B1 N1 107.52(15) . . ?
O1 B1 N1 109.64(17) . . ?

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
C7 N1 N2 C8 -176.64(15) . . . . ?
B1 N1 N2 C8 4.6(2) . . . . ?
B1 O1 C1 C2 178.37(16) . . . . ?
B1 O1 C1 C6 -2.3(3) . . . . ?
O1 C1 C2 C3 179.55(16) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 179.76(15) . . . . ?
O1 C1 C6 C5 -179.57(15) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
O1 C1 C6 C7 0.8(3) . . . . ?
C2 C1 C6 C7 -179.87(15) . . . . ?
N2 N1 C7 C6 179.66(13) . . . . ?
B1 N1 C7 C6 -1.5(3) . . . . ?
C5 C6 C7 N1 -178.54(15) . . . . ?
C1 C6 C7 N1 1.1(3) . . . . ?
N1 N2 C8 C9 178.99(13) . . . . ?
N2 C8 C9 C14 178.18(16) . . . . ?
N2 C8 C9 C10 -2.2(3) . . . . ?
C14 C9 C10 O2 -178.50(15) . . . . ?
C8 C9 C10 O2 1.9(3) . . . . ?
C14 C9 C10 C11 1.9(3) . . . . ?
C8 C9 C10 C11 -177.72(15) . . . . ?
O2 C10 C11 C12 179.11(15) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 -1.1(3) . . . . ?
C8 C9 C14 C13 178.59(14) . . . . ?
C1 O1 B1 F2 121.31(19) . . . . ?
C1 O1 B1 F1 -115.89(19) . . . . ?
C1 O1 B1 N1 1.7(3) . . . . ?
C7 N1 B1 F2 -121.59(19) . . . . ?
N2 N1 B1 F2 57.1(2) . . . . ?
C7 N1 B1 F1 118.93(18) . . . . ?
N2 N1 B1 F1 -62.4(2) . . . . ?
C7 N1 B1 O1 0.2(2) . . . . ?
N2 N1 B1 O1 178.87(13) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1523990'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-10 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         ?
_chemical_formula_sum            'C29 H20 B2 Cl2 F4 N2 O2'
_chemical_formula_weight         596.99

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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                   11.2748(14)
_cell_length_b                   14.4752(18)
_cell_length_c                   17.300(2)
_cell_angle_alpha                110.390(3)
_cell_angle_beta                 90.141(3)
_cell_angle_gamma                100.184(3)
_cell_volume                     2598.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    0.312
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31100
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.259
_diffrn_reflns_theta_max         25.207
_diffrn_reflns_theta_full        25.207
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             9279
_reflns_number_gt                7285
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.4790P] 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         9279
_refine_ls_number_parameters     739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
B1 B 0.6245(2) 0.9206(2) 0.34917(17) 0.0242(6) Uani 1 1 d . . . . .
B2 B 0.7828(2) 0.9276(2) 0.07476(16) 0.0231(6) Uani 1 1 d . . . . .
B3 B 0.1622(2) 0.5208(2) 0.41987(17) 0.0245(6) Uani 1 1 d . . . . .
B4 B 0.3524(2) 0.5607(2) 0.16401(17) 0.0247(6) Uani 1 1 d . . . . .
C1 C 0.7603(2) 0.79987(17) 0.33065(14) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.8391(2) 0.76241(18) 0.37060(14) 0.0228(5) Uani 1 1 d . . . . .
H2 H 0.8593 0.7939 0.4283 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8858(2) 0.68135(18) 0.32629(14) 0.0230(5) Uani 1 1 d . . . . .
H3 H 0.9384 0.6566 0.3540 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8588(2) 0.63208(18) 0.23967(14) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.9078(2) 0.54761(18) 0.19489(15) 0.0269(6) Uani 1 1 d . . . . .
H5 H 0.9591 0.5224 0.2231 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8829(2) 0.50144(19) 0.11179(16) 0.0313(6) Uani 1 1 d . . . . .
H6 H 0.9162 0.4443 0.0824 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8078(2) 0.5386(2) 0.06981(16) 0.0315(6) Uani 1 1 d . . . . .
H7 H 0.7913 0.5069 0.0117 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7578(2) 0.62034(18) 0.11175(15) 0.0259(6) Uani 1 1 d . . . . .
H8 H 0.7065 0.6441 0.0823 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7813(2) 0.66952(17) 0.19758(14) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.73150(19) 0.75539(17) 0.24565(14) 0.0195(5) Uani 1 1 d . . . . .
C11 C 0.65522(19) 0.79929(17) 0.20900(14) 0.0195(5) Uani 1 1 d . . . . .
H11 H 0.6372 0.7714 0.1509 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5386(2) 0.91952(17) 0.20893(14) 0.0197(5) Uani 1 1 d . . . . .
C13 C 0.4161(2) 0.91219(18) 0.21787(15) 0.0249(5) Uani 1 1 d . . . . .
H13 H 0.3788 0.8799 0.2533 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3474(2) 0.95182(18) 0.17523(15) 0.0257(6) Uani 1 1 d . . . . .
H14 H 0.2631 0.9464 0.1814 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4011(2) 0.99916(18) 0.12378(15) 0.0246(5) Uani 1 1 d . . . . .
H15 H 0.3535 1.0254 0.0941 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5241(2) 1.00829(18) 0.11551(14) 0.0229(5) Uani 1 1 d . . . . .
H16 H 0.5611 1.0407 0.0800 0.027 Uiso 1 1 calc R U . . .
C17 C 0.5934(2) 0.97011(17) 0.15906(14) 0.0194(5) Uani 1 1 d . . . . .
C18 C 0.7879(2) 1.04995(17) 0.21933(14) 0.0194(5) Uani 1 1 d . . . . .
H18 H 0.7492 1.0806 0.2678 0.023 Uiso 1 1 calc R U . . .
C19 C 0.91532(19) 1.07479(17) 0.22031(14) 0.0194(5) Uani 1 1 d . . . . .
C20 C 0.9884(2) 1.14068(17) 0.29446(14) 0.0198(5) Uani 1 1 d . . . . .
C21 C 0.9423(2) 1.17827(18) 0.37188(14) 0.0244(5) Uani 1 1 d . . . . .
H21 H 0.8587 1.1593 0.3778 0.029 Uiso 1 1 calc R U . . .
C22 C 1.0163(2) 1.24237(19) 0.43954(15) 0.0266(6) Uani 1 1 d . . . . .
H22 H 0.9832 1.2689 0.4913 0.032 Uiso 1 1 calc R U . . .
C23 C 1.1399(2) 1.26860(19) 0.43235(15) 0.0262(6) Uani 1 1 d . . . . .
H23 H 1.1907 1.3125 0.4794 0.031 Uiso 1 1 calc R U . . .
C24 C 1.1877(2) 1.23163(18) 0.35834(15) 0.0260(6) Uani 1 1 d . . . . .
H24 H 1.2721 1.2490 0.3543 0.031 Uiso 1 1 calc R U . . .
C25 C 1.1138(2) 1.16788(17) 0.28739(15) 0.0216(5) Uani 1 1 d . . . . .
C26 C 1.1624(2) 1.13211(18) 0.20941(15) 0.0248(5) Uani 1 1 d . . . . .
H26 H 1.2465 1.1517 0.2055 0.030 Uiso 1 1 calc R U . . .
C27 C 1.0934(2) 1.07097(18) 0.14010(15) 0.0240(5) Uani 1 1 d . . . . .
H27 H 1.1287 1.0489 0.0886 0.029 Uiso 1 1 calc R U . . .
C28 C 0.9689(2) 1.04060(17) 0.14534(14) 0.0207(5) Uani 1 1 d . . . . .
C29 C -0.0138(2) 0.40693(18) 0.33254(14) 0.0216(5) Uani 1 1 d . . . . .
C30 C -0.1396(2) 0.37033(19) 0.32727(15) 0.0248(5) Uani 1 1 d . . . . .
H30 H -0.1832 0.3869 0.3756 0.030 Uiso 1 1 calc R U . . .
C31 C -0.1974(2) 0.31177(18) 0.25340(15) 0.0243(5) Uani 1 1 d . . . . .
H31 H -0.2821 0.2885 0.2507 0.029 Uiso 1 1 calc R U . . .
C32 C -0.1360(2) 0.28366(17) 0.17936(14) 0.0218(5) Uani 1 1 d . . . . .
C33 C -0.1981(2) 0.22287(18) 0.10282(14) 0.0247(5) Uani 1 1 d . . . . .
H33 H -0.2827 0.1993 0.1005 0.030 Uiso 1 1 calc R U . . .
C34 C -0.1394(2) 0.19737(18) 0.03242(15) 0.0274(6) Uani 1 1 d . . . . .
H34 H -0.1827 0.1564 -0.0187 0.033 Uiso 1 1 calc R U . . .
C35 C -0.0147(2) 0.23162(18) 0.03530(15) 0.0253(5) Uani 1 1 d . . . . .
H35 H 0.0264 0.2135 -0.0141 0.030 Uiso 1 1 calc R U . . .
C36 C 0.0488(2) 0.29116(18) 0.10884(14) 0.0224(5) Uani 1 1 d . . . . .
H36 H 0.1332 0.3143 0.1097 0.027 Uiso 1 1 calc R U . . .
C37 C -0.0096(2) 0.31808(17) 0.18232(14) 0.0193(5) Uani 1 1 d . . . . .
C38 C 0.05109(19) 0.38029(17) 0.26193(14) 0.0186(5) Uani 1 1 d . . . . .
C39 C 0.1780(2) 0.41055(17) 0.27227(14) 0.0185(5) Uani 1 1 d . . . . .
H39 H 0.2245 0.3859 0.2264 0.022 Uiso 1 1 calc R U . . .
C40 C 0.36360(19) 0.49263(17) 0.34676(13) 0.0188(5) Uani 1 1 d . . . . .
C41 C 0.4289(2) 0.45197(17) 0.39078(14) 0.0207(5) Uani 1 1 d . . . . .
H41 H 0.3880 0.4154 0.4221 0.025 Uiso 1 1 calc R U . . .
C42 C 0.5531(2) 0.46467(18) 0.38907(14) 0.0236(5) Uani 1 1 d . . . . .
H42 H 0.5975 0.4367 0.4192 0.028 Uiso 1 1 calc R U . . .
C43 C 0.6124(2) 0.51787(18) 0.34373(15) 0.0241(5) Uani 1 1 d . . . . .
H43 H 0.6977 0.5252 0.3416 0.029 Uiso 1 1 calc R U . . .
C44 C 0.5481(2) 0.56080(18) 0.30109(14) 0.0237(5) Uani 1 1 d . . . . .
H44 H 0.5894 0.5976 0.2700 0.028 Uiso 1 1 calc R U . . .
C45 C 0.4246(2) 0.54993(17) 0.30395(14) 0.0198(5) Uani 1 1 d . . . . .
C46 C 0.30773(19) 0.67098(17) 0.30456(14) 0.0212(5) Uani 1 1 d . . . . .
H46 H 0.3207 0.6957 0.3631 0.025 Uiso 1 1 calc R U . . .
C47 C 0.2341(2) 0.71605(18) 0.26768(14) 0.0209(5) Uani 1 1 d . . . . .
C48 C 0.1828(2) 0.80163(17) 0.31559(14) 0.0204(5) Uani 1 1 d . . . . .
C49 C 0.2092(2) 0.85259(19) 0.40112(15) 0.0264(6) Uani 1 1 d . . . . .
H49 H 0.2616 0.8296 0.4305 0.032 Uiso 1 1 calc R U . . .
C50 C 0.1603(2) 0.9351(2) 0.44268(16) 0.0303(6) Uani 1 1 d . . . . .
H50 H 0.1787 0.9681 0.5005 0.036 Uiso 1 1 calc R U . . .
C51 C 0.0834(2) 0.97135(19) 0.40080(16) 0.0295(6) Uani 1 1 d . . . . .
H51 H 0.0505 1.0289 0.4299 0.035 Uiso 1 1 calc R U . . .
C52 C 0.0563(2) 0.92295(19) 0.31762(16) 0.0274(6) Uani 1 1 d . . . . .
H52 H 0.0041 0.9472 0.2893 0.033 Uiso 1 1 calc R U . . .
C53 C 0.1044(2) 0.83815(18) 0.27358(15) 0.0223(5) Uani 1 1 d . . . . .
C54 C 0.0770(2) 0.78829(19) 0.18708(15) 0.0251(6) Uani 1 1 d . . . . .
H54 H 0.0221 0.8115 0.1597 0.030 Uiso 1 1 calc R U . . .
C55 C 0.1263(2) 0.70897(19) 0.14226(15) 0.0252(5) Uani 1 1 d . . . . .
H55 H 0.1070 0.6781 0.0844 0.030 Uiso 1 1 calc R U . . .
C56 C 0.2063(2) 0.67269(18) 0.18226(14) 0.0219(5) Uani 1 1 d . . . . .
C57 C 0.5566(3) 0.3506(2) 0.09835(18) 0.0426(7) Uani 1 1 d . . . . .
H57A H 0.5148 0.4060 0.1007 0.051 Uiso 1 1 calc R U . . .
H57B H 0.6401 0.3805 0.1230 0.051 Uiso 1 1 calc R U . . .
C58 C 0.4549(3) 0.1537(2) 0.41930(17) 0.0358(6) Uani 1 1 d . . . . .
H58A H 0.3709 0.1158 0.4043 0.043 Uiso 1 1 calc R U . . .
H58B H 0.5040 0.1102 0.4327 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.56152(7) 0.27380(7) -0.00562(5) 0.0500(2) Uani 1 1 d . . . . .
Cl2 Cl 0.48107(6) 0.28252(6) 0.15663(4) 0.0399(2) Uani 1 1 d . . . . .
Cl3 Cl 0.51268(6) 0.18385(5) 0.33441(4) 0.0395(2) Uani 1 1 d . . . . .
Cl4 Cl 0.45701(7) 0.26257(5) 0.50647(4) 0.0409(2) Uani 1 1 d . . . . .
F1 F 0.51565(12) 0.89694(12) 0.37975(9) 0.0366(4) Uani 1 1 d . . . . .
F2 F 0.66107(13) 1.02373(10) 0.37451(8) 0.0315(4) Uani 1 1 d . . . . .
F3 F 0.71693(12) 0.92000(12) 0.00585(8) 0.0363(4) Uani 1 1 d . . . . .
F4 F 0.78592(14) 0.83366(11) 0.07753(9) 0.0379(4) Uani 1 1 d . . . . .
F5 F 0.16130(14) 0.61795(11) 0.42540(10) 0.0416(4) Uani 1 1 d . . . . .
F6 F 0.21721(12) 0.51775(12) 0.48898(8) 0.0352(4) Uani 1 1 d . . . . .
F7 F 0.33098(13) 0.45734(10) 0.13220(8) 0.0306(3) Uani 1 1 d . . . . .
F8 F 0.46102(12) 0.59979(12) 0.14156(9) 0.0342(4) Uani 1 1 d . . . . .
N1 N 0.60906(16) 0.87609(14) 0.25191(12) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.72225(16) 0.98683(14) 0.15454(11) 0.0198(4) Uani 1 1 d . . . . .
N3 N 0.23378(16) 0.47131(14) 0.34278(11) 0.0188(4) Uani 1 1 d . . . . .
N4 N 0.35842(16) 0.59695(14) 0.26138(12) 0.0203(4) Uani 1 1 d . . . . .
O1 O 0.71739(14) 0.87895(12) 0.37680(10) 0.0249(4) Uani 1 1 d . . . . .
O2 O 0.90423(14) 0.98123(12) 0.07612(9) 0.0225(4) Uani 1 1 d . . . . .
O3 O 0.03876(14) 0.46408(13) 0.40625(9) 0.0243(4) Uani 1 1 d . . . . .
O4 O 0.25247(15) 0.59502(13) 0.13617(10) 0.0266(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.372(3) . ?
B1 F2 1.385(3) . ?
B1 O1 1.453(3) . ?
B1 N1 1.575(3) . ?
B2 F3 1.364(3) . ?
B2 F4 1.384(3) . ?
B2 O2 1.445(3) . ?
B2 N2 1.579(3) . ?
B3 F6 1.364(3) . ?
B3 F5 1.378(3) . ?
B3 O3 1.458(3) . ?
B3 N3 1.577(3) . ?
B4 F8 1.371(3) . ?
B4 F7 1.378(3) . ?
B4 O4 1.453(3) . ?
B4 N4 1.578(3) . ?
C1 O1 1.320(3) . ?
C1 C10 1.395(3) . ?
C1 C2 1.410(3) . ?
C2 C3 1.355(3) . ?
C3 C4 1.422(3) . ?
C4 C5 1.407(3) . ?
C4 C9 1.424(3) . ?
C5 C6 1.362(4) . ?
C6 C7 1.401(3) . ?
C7 C8 1.373(3) . ?
C8 C9 1.406(3) . ?
C9 C10 1.442(3) . ?
C10 C11 1.420(3) . ?
C11 N1 1.300(3) . ?
C12 C13 1.379(3) . ?
C12 C17 1.395(3) . ?
C12 N1 1.442(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.387(3) . ?
C17 N2 1.436(3) . ?
C18 N2 1.297(3) . ?
C18 C19 1.417(3) . ?
C19 C28 1.398(3) . ?
C19 C20 1.449(3) . ?
C20 C21 1.399(3) . ?
C20 C25 1.417(3) . ?
C21 C22 1.376(3) . ?
C22 C23 1.395(3) . ?
C23 C24 1.358(3) . ?
C24 C25 1.409(3) . ?
C25 C26 1.416(3) . ?
C26 C27 1.356(3) . ?
C27 C28 1.408(3) . ?
C28 O2 1.327(3) . ?
C29 O3 1.323(3) . ?
C29 C38 1.397(3) . ?
C29 C30 1.414(3) . ?
C30 C31 1.350(3) . ?
C31 C32 1.424(3) . ?
C32 C33 1.409(3) . ?
C32 C37 1.418(3) . ?
C33 C34 1.355(3) . ?
C34 C35 1.400(3) . ?
C35 C36 1.374(3) . ?
C36 C37 1.397(3) . ?
C37 C38 1.446(3) . ?
C38 C39 1.412(3) . ?
C39 N3 1.308(3) . ?
C40 C41 1.389(3) . ?
C40 C45 1.392(3) . ?
C40 N3 1.438(3) . ?
C41 C42 1.382(3) . ?
C42 C43 1.378(3) . ?
C43 C44 1.390(3) . ?
C44 C45 1.376(3) . ?
C45 N4 1.445(3) . ?
C46 N4 1.302(3) . ?
C46 C47 1.415(3) . ?
C47 C56 1.399(3) . ?
C47 C48 1.447(3) . ?
C48 C49 1.408(3) . ?
C48 C53 1.421(3) . ?
C49 C50 1.372(3) . ?
C50 C51 1.405(3) . ?
C51 C52 1.369(4) . ?
C52 C53 1.402(3) . ?
C53 C54 1.422(3) . ?
C54 C55 1.355(3) . ?
C55 C56 1.410(3) . ?
C56 O4 1.325(3) . ?
C57 Cl1 1.761(3) . ?
C57 Cl2 1.764(3) . ?
C58 Cl4 1.758(3) . ?
C58 Cl3 1.767(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
F1 B1 F2 110.3(2) . . ?
F1 B1 O1 111.3(2) . . ?
F2 B1 O1 108.8(2) . . ?
F1 B1 N1 108.7(2) . . ?
F2 B1 N1 108.8(2) . . ?
O1 B1 N1 108.85(19) . . ?
F3 B2 F4 110.9(2) . . ?
F3 B2 O2 110.0(2) . . ?
F4 B2 O2 110.0(2) . . ?
F3 B2 N2 109.66(19) . . ?
F4 B2 N2 107.37(19) . . ?
O2 B2 N2 108.8(2) . . ?
F6 B3 F5 111.6(2) . . ?
F6 B3 O3 110.2(2) . . ?
F5 B3 O3 109.7(2) . . ?
F6 B3 N3 108.98(19) . . ?
F5 B3 N3 107.9(2) . . ?
O3 B3 N3 108.36(19) . . ?
F8 B4 F7 110.9(2) . . ?
F8 B4 O4 111.9(2) . . ?
F7 B4 O4 108.7(2) . . ?
F8 B4 N4 107.8(2) . . ?
F7 B4 N4 109.0(2) . . ?
O4 B4 N4 108.51(19) . . ?
O1 C1 C10 122.1(2) . . ?
O1 C1 C2 117.2(2) . . ?
C10 C1 C2 120.7(2) . . ?
C3 C2 C1 119.7(2) . . ?
C2 C3 C4 122.2(2) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 C9 119.5(2) . . ?
C3 C4 C9 119.2(2) . . ?
C6 C5 C4 121.1(2) . . ?
C5 C6 C7 119.7(2) . . ?
C8 C7 C6 120.7(2) . . ?
C7 C8 C9 121.1(2) . . ?
C8 C9 C4 118.0(2) . . ?
C8 C9 C10 124.0(2) . . ?
C4 C9 C10 118.0(2) . . ?
C1 C10 C11 117.7(2) . . ?
C1 C10 C9 120.2(2) . . ?
C11 C10 C9 122.1(2) . . ?
N1 C11 C10 122.5(2) . . ?
C13 C12 C17 119.6(2) . . ?
C13 C12 N1 119.9(2) . . ?
C17 C12 N1 120.57(19) . . ?
C12 C13 C14 120.1(2) . . ?
C15 C14 C13 120.3(2) . . ?
C14 C15 C16 120.0(2) . . ?
C15 C16 C17 119.9(2) . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 N2 119.1(2) . . ?
C12 C17 N2 120.74(19) . . ?
N2 C18 C19 122.3(2) . . ?
C28 C19 C18 117.8(2) . . ?
C28 C19 C20 120.1(2) . . ?
C18 C19 C20 121.9(2) . . ?
C21 C20 C25 118.7(2) . . ?
C21 C20 C19 123.8(2) . . ?
C25 C20 C19 117.5(2) . . ?
C22 C21 C20 120.8(2) . . ?
C21 C22 C23 120.3(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 121.0(2) . . ?
C24 C25 C26 121.2(2) . . ?
C24 C25 C20 119.0(2) . . ?
C26 C25 C20 119.7(2) . . ?
C27 C26 C25 122.5(2) . . ?
C26 C27 C28 119.2(2) . . ?
O2 C28 C19 121.6(2) . . ?
O2 C28 C27 117.5(2) . . ?
C19 C28 C27 120.9(2) . . ?
O3 C29 C38 122.3(2) . . ?
O3 C29 C30 117.6(2) . . ?
C38 C29 C30 120.1(2) . . ?
C31 C30 C29 119.8(2) . . ?
C30 C31 C32 122.3(2) . . ?
C33 C32 C37 119.1(2) . . ?
C33 C32 C31 121.4(2) . . ?
C37 C32 C31 119.5(2) . . ?
C34 C33 C32 121.2(2) . . ?
C33 C34 C35 119.8(2) . . ?
C36 C35 C34 120.7(2) . . ?
C35 C36 C37 120.7(2) . . ?
C36 C37 C32 118.7(2) . . ?
C36 C37 C38 123.8(2) . . ?
C32 C37 C38 117.5(2) . . ?
C29 C38 C39 117.6(2) . . ?
C29 C38 C37 120.7(2) . . ?
C39 C38 C37 121.6(2) . . ?
N3 C39 C38 122.3(2) . . ?
C41 C40 C45 119.6(2) . . ?
C41 C40 N3 119.7(2) . . ?
C45 C40 N3 120.70(19) . . ?
C42 C41 C40 120.2(2) . . ?
C43 C42 C41 120.0(2) . . ?
C42 C43 C44 120.2(2) . . ?
C45 C44 C43 119.9(2) . . ?
C44 C45 C40 120.0(2) . . ?
C44 C45 N4 119.8(2) . . ?
C40 C45 N4 120.17(19) . . ?
N4 C46 C47 122.5(2) . . ?
C56 C47 C46 118.0(2) . . ?
C56 C47 C48 119.6(2) . . ?
C46 C47 C48 122.3(2) . . ?
C49 C48 C53 118.1(2) . . ?
C49 C48 C47 123.6(2) . . ?
C53 C48 C47 118.2(2) . . ?
C50 C49 C48 120.8(2) . . ?
C49 C50 C51 120.8(2) . . ?
C52 C51 C50 119.3(2) . . ?
C51 C52 C53 121.1(2) . . ?
C52 C53 C48 119.7(2) . . ?
C52 C53 C54 121.1(2) . . ?
C48 C53 C54 119.1(2) . . ?
C55 C54 C53 122.4(2) . . ?
C54 C55 C56 119.4(2) . . ?
O4 C56 C47 121.4(2) . . ?
O4 C56 C55 117.5(2) . . ?
C47 C56 C55 121.1(2) . . ?
Cl1 C57 Cl2 111.80(17) . . ?
Cl4 C58 Cl3 111.13(15) . . ?
C11 N1 C12 118.71(19) . . ?
C11 N1 B1 121.95(19) . . ?
C12 N1 B1 119.31(18) . . ?
C18 N2 C17 117.79(19) . . ?
C18 N2 B2 120.78(19) . . ?
C17 N2 B2 121.39(18) . . ?
C39 N3 C40 117.13(18) . . ?
C39 N3 B3 121.65(19) . . ?
C40 N3 B3 121.21(18) . . ?
C46 N4 C45 119.08(19) . . ?
C46 N4 B4 121.04(19) . . ?
C45 N4 B4 119.85(18) . . ?
C1 O1 B1 125.10(19) . . ?
C28 O2 B2 123.19(18) . . ?
C29 O3 B3 123.97(18) . . ?
C56 O4 B4 124.23(19) . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1523988'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-10 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         ?
_chemical_formula_sum            'C28 H18 B2 F4 N2 O2'
_chemical_formula_weight         512.06

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'
O O 0.0492 0.0322 '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'

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

_cell_length_a                   10.5217(9)
_cell_length_b                   12.6033(10)
_cell_length_c                   16.7317(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2218.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7797
_cell_measurement_theta_min      5.29
_cell_measurement_theta_max      65.32

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    1.002
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12464
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.287
_diffrn_reflns_theta_max         65.666
_diffrn_reflns_theta_full        65.666
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             1857
_reflns_number_gt                1736
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0607P)²+8.8386P] 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         1857
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.2133
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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
B1 B 0.8407(5) 0.8592(5) 0.3657(3) 0.0403(13) Uani 1 1 d . . . . .
C1 C 0.6231(4) 0.8633(4) 0.4160(3) 0.0352(10) Uani 1 1 d . . . . .
C2 C 0.5259(4) 0.8063(4) 0.4568(3) 0.0406(11) Uani 1 1 d . . . . .
H2 H 0.5456 0.7416 0.4831 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4061(5) 0.8440(4) 0.4580(3) 0.0411(11) Uani 1 1 d . . . . .
H3 H 0.3421 0.8039 0.4844 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3720(4) 0.9415(4) 0.4212(3) 0.0370(11) Uani 1 1 d . . . . .
C5 C 0.2474(5) 0.9809(4) 0.4270(3) 0.0413(11) Uani 1 1 d . . . . .
H5 H 0.1838 0.9396 0.4527 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2172(5) 1.0768(4) 0.3966(3) 0.0447(12) Uani 1 1 d . . . . .
H6 H 0.1327 1.1026 0.4009 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3101(5) 1.1384(4) 0.3585(3) 0.0479(13) Uani 1 1 d . . . . .
H7 H 0.2886 1.2064 0.3380 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4316(4) 1.1011(4) 0.3508(3) 0.0414(11) Uani 1 1 d . . . . .
H8 H 0.4932 1.1432 0.3240 0.050 Uiso 1 1 calc R U . . .
C9 C 0.4671(4) 1.0011(4) 0.3818(3) 0.0347(10) Uani 1 1 d . . . . .
C10 C 0.5946(4) 0.9590(4) 0.3778(3) 0.0338(10) Uani 1 1 d . . . . .
C11 C 0.6946(4) 1.0118(4) 0.3380(3) 0.0371(11) Uani 1 1 d . . . . .
H11 H 0.6774 1.0790 0.3147 0.045 Uiso 1 1 calc R U . . .
C12 C 0.9066(4) 1.0317(3) 0.2907(3) 0.0353(10) Uani 1 1 d . . . . .
C13 C 0.9080(4) 1.1424(4) 0.2924(3) 0.0416(11) Uani 1 1 d . . . . .
H13 H 0.8464 1.1803 0.3225 0.050 Uiso 1 1 calc R U . . .
C14 C 1.0000 1.1958(5) 0.2500 0.0449(17) Uani 1 2 d S T P . .
H14 H 1.0000 1.2712 0.2500 0.054 Uiso 1 2 calc R U P . .
C15 C 1.0000 0.9766(5) 0.2500 0.0356(14) Uani 1 2 d S T P . .
H15 H 1.0000 0.9012 0.2500 0.043 Uiso 1 2 calc R U P . .
F1 F 0.9513(3) 0.8644(3) 0.40846(19) 0.0567(9) Uani 1 1 d . . . . .
F2 F 0.8523(3) 0.7892(2) 0.30201(18) 0.0519(8) Uani 1 1 d . . . . .
N1 N 0.8090(3) 0.9737(3) 0.3314(2) 0.0329(9) Uani 1 1 d . . . . .
O1 O 0.7380(3) 0.8230(3) 0.41656(18) 0.0397(8) 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
B1 F1 1.369(6) . ?
B1 F2 1.388(6) . ?
B1 O1 1.449(6) . ?
B1 N1 1.588(7) . ?
C1 O1 1.312(5) . ?
C1 C10 1.398(6) . ?
C1 C2 1.423(6) . ?
C2 C3 1.348(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.421(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(7) . ?
C4 C9 1.415(6) . ?
C5 C6 1.350(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.413(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.444(6) . ?
C10 C11 1.412(6) . ?
C11 N1 1.301(5) . ?
C11 H11 0.9500 . ?
C12 C15 1.383(5) . ?
C12 C13 1.396(6) . ?
C12 N1 1.433(6) . ?
C13 C14 1.376(6) . ?
C13 H13 0.9500 . ?
C14 C13 1.377(6) 3_755 ?
C14 H14 0.9500 . ?
C15 C12 1.383(5) 3_755 ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 110.9(4) . . ?
F1 B1 O1 110.0(4) . . ?
F2 B1 O1 108.5(4) . . ?
F1 B1 N1 108.9(4) . . ?
F2 B1 N1 108.6(4) . . ?
O1 B1 N1 110.0(4) . . ?
O1 C1 C10 122.4(4) . . ?
O1 C1 C2 117.6(4) . . ?
C10 C1 C2 120.1(4) . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 122.3(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C9 120.3(4) . . ?
C5 C4 C3 120.7(4) . . ?
C9 C4 C3 118.9(4) . . ?
C6 C5 C4 120.6(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.3(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 117.2(4) . . ?
C8 C9 C10 123.8(4) . . ?
C4 C9 C10 118.9(4) . . ?
C1 C10 C11 117.5(4) . . ?
C1 C10 C9 119.7(4) . . ?
C11 C10 C9 122.7(4) . . ?
N1 C11 C10 123.8(4) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C15 C12 C13 120.3(5) . . ?
C15 C12 N1 119.2(4) . . ?
C13 C12 N1 120.5(4) . . ?
C14 C13 C12 119.1(5) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C13 121.4(6) . 3_755 ?
C13 C14 H14 119.3 . . ?
C13 C14 H14 119.3 3_755 . ?
C12 C15 C12 119.7(6) 3_755 . ?
C12 C15 H15 120.1 3_755 . ?
C12 C15 H15 120.1 . . ?
C11 N1 C12 121.0(4) . . ?
C11 N1 B1 119.9(4) . . ?
C12 N1 B1 119.0(3) . . ?
C1 O1 B1 124.1(4) . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1523991'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-10 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         ?
_chemical_formula_sum            'C32 H30 B2 F4 N2 O4 S2'
_chemical_formula_weight         668.32

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'
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'
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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.6836(7)
_cell_length_b                   5.6340(4)
_cell_length_c                   27.2833(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.073(2)
_cell_angle_gamma                90
_cell_volume                     1480.15(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.20

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17125
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.501
_diffrn_reflns_theta_max         25.224
_diffrn_reflns_theta_full        25.224
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2661
_reflns_number_gt                2353
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.2476P] 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         2661
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
B1 B 0.77147(19) 0.6148(4) 0.07887(7) 0.0189(4) Uani 1 1 d . . . . .
C1 C 0.59890(16) 0.5226(3) 0.15496(6) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.70427(17) 0.3655(3) 0.14532(6) 0.0178(4) Uani 1 1 d . . . . .
C3 C 0.73361(17) 0.1631(3) 0.17492(6) 0.0198(4) Uani 1 1 d . . . . .
H3 H 0.8014 0.0520 0.1668 0.024 Uiso 1 1 calc R U . . .
C4 C 0.66426(16) 0.1276(3) 0.21520(6) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.6827 -0.0120 0.2343 0.023 Uiso 1 1 calc R U . . .
C5 C 0.56483(17) 0.2935(3) 0.22955(6) 0.0186(4) Uani 1 1 d . . . . .
C6 C 0.50482(18) 0.2643(3) 0.27396(7) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.5272 0.1283 0.2938 0.024 Uiso 1 1 calc R U . . .
C7 C 0.41431(17) 0.4302(3) 0.28881(6) 0.0210(4) Uani 1 1 d . . . . .
H7 H 0.3751 0.4107 0.3190 0.025 Uiso 1 1 calc R U . . .
C8 C 0.38006(17) 0.6289(3) 0.25897(6) 0.0208(4) Uani 1 1 d . . . . .
H8 H 0.3170 0.7432 0.2692 0.025 Uiso 1 1 calc R U . . .
C9 C 0.43604(17) 0.6614(3) 0.21519(6) 0.0188(4) Uani 1 1 d . . . . .
H9 H 0.4107 0.7968 0.1955 0.023 Uiso 1 1 calc R U . . .
C10 C 0.53071(16) 0.4954(3) 0.19930(6) 0.0172(4) Uani 1 1 d . . . . .
C11 C 0.55301(17) 0.6888(3) 0.11752(6) 0.0175(4) Uani 1 1 d . . . . .
H11 H 0.4700 0.7756 0.1202 0.021 Uiso 1 1 calc R U . . .
C12 C 0.55937(17) 0.8660(3) 0.03901(6) 0.0177(4) Uani 1 1 d . . . . .
C13 C 0.42770(17) 0.8089(3) 0.01700(6) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.3790 0.6774 0.0286 0.024 Uiso 1 1 calc R U . . .
C14 C 0.63258(17) 1.0551(3) 0.02210(6) 0.0193(4) Uani 1 1 d . . . . .
H14 H 0.7231 1.0916 0.0371 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0970(2) 0.1244(4) 0.05198(7) 0.0316(5) Uani 1 1 d . . . . .
H15A H 0.1226 -0.0040 0.0305 0.047 Uiso 1 1 calc R U . . .
H15B H 0.0540 0.2541 0.0318 0.047 Uiso 1 1 calc R U . . .
H15C H 0.0309 0.0645 0.0739 0.047 Uiso 1 1 calc R U . . .
C16 C 0.1620(2) 0.4440(4) 0.12220(8) 0.0332(5) Uani 1 1 d . . . . .
H16A H 0.0880 0.3653 0.1380 0.050 Uiso 1 1 calc R U . . .
H16B H 0.1216 0.5679 0.0999 0.050 Uiso 1 1 calc R U . . .
H16C H 0.2285 0.5158 0.1475 0.050 Uiso 1 1 calc R U . . .
F1 F 0.79722(10) 0.56579(18) 0.03123(4) 0.0252(3) Uani 1 1 d . . . . .
F2 F 0.86779(10) 0.77471(17) 0.10063(4) 0.0248(3) Uani 1 1 d . . . . .
N1 N 0.62163(14) 0.7256(2) 0.07948(5) 0.0168(3) Uani 1 1 d . . . . .
O1 O 0.77587(11) 0.3936(2) 0.10667(4) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.29592(13) 0.0362(2) 0.12323(5) 0.0308(4) Uani 1 1 d . . . . .
S1 S 0.24897(4) 0.23149(8) 0.08808(2) 0.02316(19) 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
B1 F1 1.377(2) . ?
B1 F2 1.384(2) . ?
B1 O1 1.457(2) . ?
B1 N1 1.581(2) . ?
C1 C2 1.397(2) . ?
C1 C11 1.422(2) . ?
C1 C10 1.446(2) . ?
C2 O1 1.3315(19) . ?
C2 C3 1.409(2) . ?
C3 C4 1.362(2) . ?
C4 C5 1.426(2) . ?
C5 C6 1.408(3) . ?
C5 C10 1.424(2) . ?
C6 C7 1.372(2) . ?
C7 C8 1.403(2) . ?
C8 C9 1.375(2) . ?
C9 C10 1.410(2) . ?
C11 N1 1.307(2) . ?
C12 C14 1.386(2) . ?
C12 C13 1.388(2) . ?
C12 N1 1.438(2) . ?
C13 C14 1.391(2) 3_675 ?
C14 C13 1.391(2) 3_675 ?
C15 S1 1.7872(19) . ?
C16 S1 1.782(2) . ?
O2 S1 1.4981(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
F1 B1 F2 110.75(14) . . ?
F1 B1 O1 108.75(14) . . ?
F2 B1 O1 110.61(14) . . ?
F1 B1 N1 110.32(14) . . ?
F2 B1 N1 108.42(14) . . ?
O1 B1 N1 107.96(13) . . ?
C2 C1 C11 117.47(15) . . ?
C2 C1 C10 119.84(15) . . ?
C11 C1 C10 122.34(14) . . ?
O1 C2 C1 121.71(15) . . ?
O1 C2 C3 117.39(14) . . ?
C1 C2 C3 120.81(15) . . ?
C4 C3 C2 119.65(15) . . ?
C3 C4 C5 122.01(16) . . ?
C6 C5 C10 120.06(15) . . ?
C6 C5 C4 120.77(15) . . ?
C10 C5 C4 119.12(15) . . ?
C7 C6 C5 120.62(16) . . ?
C6 C7 C8 119.44(15) . . ?
C9 C8 C7 121.30(16) . . ?
C8 C9 C10 120.51(16) . . ?
C9 C10 C5 118.06(15) . . ?
C9 C10 C1 123.80(15) . . ?
C5 C10 C1 118.11(15) . . ?
N1 C11 C1 121.91(15) . . ?
C14 C12 C13 120.87(16) . . ?
C14 C12 N1 119.40(14) . . ?
C13 C12 N1 119.73(15) . . ?
C12 C13 C14 119.71(16) . 3_675 ?
C12 C14 C13 119.41(15) . 3_675 ?
C11 N1 C12 119.34(14) . . ?
C11 N1 B1 119.34(14) . . ?
C12 N1 B1 121.31(13) . . ?
C2 O1 B1 121.67(13) . . ?
O2 S1 C16 106.70(9) . . ?
O2 S1 C15 106.34(9) . . ?
C16 S1 C15 96.16(9) . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1523989'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-10 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         ?
_chemical_formula_sum            'C22 H15 B F2 N2 O2'
_chemical_formula_weight         388.17

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'
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'
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'

_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                   8.1614(12)
_cell_length_b                   9.4911(14)
_cell_length_c                   11.3018(18)
_cell_angle_alpha                94.706(7)
_cell_angle_beta                 101.989(5)
_cell_angle_gamma                92.791(7)
_cell_volume                     851.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6224
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.14

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.449
_exptl_crystal_size_min          0.372
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8627
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.850
_diffrn_reflns_theta_max         25.148
_diffrn_reflns_theta_full        25.148
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2951
_reflns_number_gt                2540
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1013P)²+26.2575P] 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         2951
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.1410
_refine_ls_wR_factor_ref         0.4405
_refine_ls_wR_factor_gt          0.4363
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
F2 F 0.7288(7) 0.3398(6) 0.7056(5) 0.0212(13) Uani 1 1 d . . . . .
F1 F 0.9718(7) 0.3005(6) 0.6439(5) 0.0238(14) Uani 1 1 d . . . . .
C11 C 0.9324(11) 0.6362(9) 0.6085(8) 0.0129(19) Uani 1 1 d . . . . .
H11 H 0.9197 0.6956 0.5440 0.015 Uiso 1 1 calc R U . . .
O1 O 0.9681(9) 0.4746(7) 0.8038(6) 0.0197(15) Uani 1 1 d . . . . .
C1 C 1.0540(12) 0.5976(10) 0.8156(9) 0.018(2) Uani 1 1 d . . . . .
O2 O 0.6328(9) 0.5696(7) 0.2605(7) 0.0238(17) Uani 1 1 d . . . . .
H2 H 0.6721 0.5892 0.3352 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1811(12) -0.0095(10) 0.2277(9) 0.019(2) Uani 1 1 d . . . . .
H17 H 0.1060 -0.0914 0.2039 0.023 Uiso 1 1 calc R U . . .
C2 C 1.1462(12) 0.6507(10) 0.9329(9) 0.018(2) Uani 1 1 d . . . . .
H2A H 1.1467 0.5964 0.9999 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6373(12) 0.3794(10) 0.4490(9) 0.019(2) Uani 1 1 d . . . . .
H12 H 0.6378 0.3111 0.5061 0.023 Uiso 1 1 calc R U . . .
C20 C 0.3148(12) 0.3129(10) 0.0965(9) 0.020(2) Uani 1 1 d . . . . .
H20 H 0.2438 0.2998 0.0179 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3925(12) 0.1291(10) 0.3810(9) 0.020(2) Uani 1 1 d . . . . .
H15 H 0.4586 0.1415 0.4613 0.024 Uiso 1 1 calc R U . . .
C10 C 1.0458(12) 0.6829(10) 0.7189(9) 0.016(2) Uani 1 1 d . . . . .
C22 C 0.5293(12) 0.4516(10) 0.2433(10) 0.020(2) Uani 1 1 d . . . . .
C18 C 0.1934(12) 0.0881(10) 0.1485(9) 0.020(2) Uani 1 1 d . . . . .
H18 H 0.1236 0.0748 0.0695 0.024 Uiso 1 1 calc R U . . .
C8 C 1.1460(12) 0.9057(10) 0.6402(9) 0.017(2) Uani 1 1 d . . . . .
H8 H 1.0872 0.8742 0.5600 0.020 Uiso 1 1 calc R U . . .
C21 C 0.4207(12) 0.4288(11) 0.1271(9) 0.022(2) Uani 1 1 d . . . . .
H21 H 0.4230 0.4966 0.0701 0.026 Uiso 1 1 calc R U . . .
N1 N 0.8436(9) 0.5138(8) 0.5912(7) 0.0142(17) Uani 1 1 d . . . . .
C14 C 0.4109(11) 0.2315(10) 0.3000(9) 0.018(2) Uani 1 1 d . . . . .
C7 C 1.2319(13) 1.0344(11) 0.6615(10) 0.023(2) Uani 1 1 d . . . . .
H7 H 1.2337 1.0905 0.5959 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5269(12) 0.3574(10) 0.3294(9) 0.016(2) Uani 1 1 d . . . . .
C3 C 1.2336(12) 0.7790(10) 0.9498(9) 0.019(2) Uani 1 1 d . . . . .
H3 H 1.2961 0.8116 1.0288 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2824(12) 0.0126(10) 0.3471(10) 0.021(2) Uani 1 1 d . . . . .
H16 H 0.2735 -0.0543 0.4039 0.025 Uiso 1 1 calc R U . . .
C6 C 1.3194(12) 1.0866(11) 0.7804(10) 0.022(2) Uani 1 1 d . . . . .
H6 H 1.3764 1.1781 0.7955 0.026 Uiso 1 1 calc R U . . .
C9 C 1.1416(12) 0.8168(10) 0.7347(9) 0.017(2) Uani 1 1 d . . . . .
C4 C 1.2346(12) 0.8664(10) 0.8529(9) 0.018(2) Uani 1 1 d . . . . .
C19 C 0.3065(12) 0.2088(10) 0.1797(9) 0.018(2) Uani 1 1 d . . . . .
C5 C 1.3193(12) 1.0020(10) 0.8723(9) 0.020(2) Uani 1 1 d . . . . .
H5 H 1.3782 1.0357 0.9520 0.024 Uiso 1 1 calc R U . . .
B1 B 0.8757(13) 0.4002(11) 0.6878(9) 0.014(2) Uani 1 1 d . . . . .
N2 N 0.7351(9) 0.4942(8) 0.4760(7) 0.0162(17) 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
F2 B1 1.363(12) . ?
F1 B1 1.383(12) . ?
C11 N1 1.317(12) . ?
C11 C10 1.414(13) . ?
C11 H11 0.9500 . ?
O1 C1 1.315(12) . ?
O1 B1 1.473(12) . ?
C1 C10 1.405(13) . ?
C1 C2 1.421(14) . ?
O2 C22 1.346(12) . ?
O2 H2 0.8400 . ?
C17 C18 1.354(14) . ?
C17 C16 1.422(14) . ?
C17 H17 0.9500 . ?
C2 C3 1.359(14) . ?
C2 H2A 0.9500 . ?
C12 N2 1.295(12) . ?
C12 C13 1.454(14) . ?
C12 H12 0.9500 . ?
C20 C21 1.341(15) . ?
C20 C19 1.427(14) . ?
C20 H20 0.9500 . ?
C15 C16 1.366(14) . ?
C15 C14 1.412(14) . ?
C15 H15 0.9500 . ?
C10 C9 1.437(13) . ?
C22 C13 1.377(14) . ?
C22 C21 1.416(14) . ?
C18 C19 1.408(14) . ?
C18 H18 0.9500 . ?
C8 C7 1.357(14) . ?
C8 C9 1.419(13) . ?
C8 H8 0.9500 . ?
C21 H21 0.9500 . ?
N1 N2 1.407(11) . ?
N1 B1 1.589(12) . ?
C14 C19 1.441(14) . ?
C14 C13 1.459(13) . ?
C7 C6 1.421(15) . ?
C7 H7 0.9500 . ?
C3 C4 1.428(14) . ?
C3 H3 0.9500 . ?
C16 H16 0.9500 . ?
C6 C5 1.364(14) . ?
C6 H6 0.9500 . ?
C9 C4 1.422(14) . ?
C4 C5 1.410(14) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C11 C10 122.8(8) . . ?
N1 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C1 O1 B1 125.1(8) . . ?
O1 C1 C10 122.3(9) . . ?
O1 C1 C2 118.3(8) . . ?
C10 C1 C2 119.1(9) . . ?
C22 O2 H2 109.5 . . ?
C18 C17 C16 118.8(9) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C3 C2 C1 120.3(9) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
N2 C12 C13 118.4(9) . . ?
N2 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C21 C20 C19 121.3(9) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C16 C15 C14 121.9(9) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C1 C10 C11 117.5(9) . . ?
C1 C10 C9 120.9(9) . . ?
C11 C10 C9 121.5(8) . . ?
O2 C22 C13 124.0(9) . . ?
O2 C22 C21 114.8(9) . . ?
C13 C22 C21 121.2(9) . . ?
C17 C18 C19 122.1(9) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C7 C8 C9 121.7(9) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C20 C21 C22 121.0(10) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C11 N1 N2 112.0(7) . . ?
C11 N1 B1 121.3(8) . . ?
N2 N1 B1 126.3(7) . . ?
C15 C14 C19 117.0(9) . . ?
C15 C14 C13 125.0(9) . . ?
C19 C14 C13 118.1(9) . . ?
C8 C7 C6 121.1(10) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C22 C13 C12 121.9(9) . . ?
C22 C13 C14 119.3(9) . . ?
C12 C13 C14 118.8(9) . . ?
C2 C3 C4 122.2(9) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C15 C16 C17 120.7(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C5 C6 C7 118.3(9) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C8 C9 C4 117.4(9) . . ?
C8 C9 C10 124.2(9) . . ?
C4 C9 C10 118.4(9) . . ?
C5 C4 C9 119.4(9) . . ?
C5 C4 C3 121.9(9) . . ?
C9 C4 C3 118.7(9) . . ?
C18 C19 C20 121.5(9) . . ?
C18 C19 C14 119.4(9) . . ?
C20 C19 C14 119.0(9) . . ?
C6 C5 C4 122.2(9) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
F2 B1 F1 111.6(8) . . ?
F2 B1 O1 108.5(7) . . ?
F1 B1 O1 110.9(8) . . ?
F2 B1 N1 111.6(8) . . ?
F1 B1 N1 106.5(7) . . ?
O1 B1 N1 107.6(8) . . ?
C12 N2 N1 118.1(8) . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.184

