# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_e1445a_a
_database_code_depnum_ccdc_archive 'CCDC 2090001'
loop_
_audit_author_name
_audit_author_address
'Andrzej Wojtczak'
;Nicolaus Copernicus University
Poland
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 B F2 N2 O'
_chemical_formula_sum            'C19 H17 B F2 N2 O'
_chemical_formula_weight         338.15

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9326(10)
_cell_length_b                   8.4946(9)
_cell_length_c                   12.4339(14)
_cell_angle_alpha                83.493(9)
_cell_angle_beta                 75.117(10)
_cell_angle_gamma                84.165(10)
_cell_volume                     802.22(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1561
_cell_measurement_theta_min      2.4300
_cell_measurement_theta_max      27.2810

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.703
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.208
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_exptl_absorpt_special_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            5246
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.420
_diffrn_reflns_theta_max         28.227
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3516
_reflns_number_gt                2256
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB-2017 (Sheldrick, 2017)'
_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)+(0.0615P)²+0.0636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.051(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3516
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.7424(2) 0.34517(14) 0.62139(11) 0.0531(4) Uani 1 1 d . . . . .
B1 B 0.7777(3) 0.3987(2) 0.72024(19) 0.0424(5) Uani 1 1 d . . . . .
F1 F 0.63600(16) 0.37261(13) 0.80968(9) 0.0615(4) Uani 1 1 d . . . . .
F2 F 0.92729(16) 0.31292(12) 0.74078(10) 0.0615(4) Uani 1 1 d . . . . .
N1 N 0.81074(19) 0.58330(16) 0.70209(12) 0.0361(4) Uani 1 1 d . . . . .
C1 C 0.8396(2) 0.66132(19) 0.78889(15) 0.0378(4) Uani 1 1 d . . . . .
C2 C 0.8345(3) 0.5827(2) 0.89527(17) 0.0482(5) Uani 1 1 d . . . . .
H2A H 0.813650 0.475665 0.909067 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8600(3) 0.6628(2) 0.97889(17) 0.0524(5) Uani 1 1 d . . . . .
H3A H 0.854601 0.609212 1.049060 0.063 Uiso 1 1 calc R U . . .
C4 C 0.8940(3) 0.8233(2) 0.96090(19) 0.0535(5) Uani 1 1 d . . . . .
H4A H 0.912642 0.875583 1.018135 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8995(3) 0.9022(2) 0.85817(18) 0.0501(5) Uani 1 1 d . . . . .
H5A H 0.921132 1.009151 0.846047 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8730(2) 0.8243(2) 0.77015(16) 0.0402(4) Uani 1 1 d . . . . .
C7 C 0.8769(2) 0.9050(2) 0.66318(16) 0.0450(5) Uani 1 1 d . . . . .
H7A H 0.898955 1.011840 0.649410 0.054 Uiso 1 1 calc R U . . .
C8 C 0.8489(2) 0.8271(2) 0.58164(16) 0.0431(5) Uani 1 1 d . . . . .
H8A H 0.852670 0.880816 0.511697 0.052 Uiso 1 1 calc R U . . .
C9 C 0.8133(2) 0.66290(19) 0.60081(15) 0.0363(4) Uani 1 1 d . . . . .
C10 C 0.7804(2) 0.5876(2) 0.51375(15) 0.0406(5) Uani 1 1 d . . . . .
H10A H 0.784121 0.646244 0.445434 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7435(2) 0.4326(2) 0.52533(15) 0.0383(4) Uani 1 1 d . . . . .
C12 C 0.7053(2) 0.3504(2) 0.43786(15) 0.0390(4) Uani 1 1 d . . . . .
C13 C 0.6999(3) 0.4253(2) 0.33240(17) 0.0490(5) Uani 1 1 d . . . . .
H13A H 0.720426 0.532398 0.316949 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6654(3) 0.3461(2) 0.25098(17) 0.0495(5) Uani 1 1 d . . . . .
H14A H 0.662831 0.400768 0.182180 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6339(2) 0.1839(2) 0.26944(16) 0.0420(5) Uani 1 1 d . . . . .
C16 C 0.6374(3) 0.1089(2) 0.37601(16) 0.0458(5) Uani 1 1 d . . . . .
H16A H 0.616203 0.002051 0.392081 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6714(2) 0.1901(2) 0.45676(16) 0.0423(5) Uani 1 1 d . . . . .
H17A H 0.671784 0.136495 0.526214 0.051 Uiso 1 1 calc R U . . .
N2 N 0.6008(2) 0.1037(2) 0.18793(14) 0.0577(5) Uani 1 1 d . . . . .
C18 C 0.6048(3) 0.1818(3) 0.07673(17) 0.0597(6) Uani 1 1 d . . . . .
H18A H 0.578757 0.107961 0.031318 0.072 Uiso 1 1 calc R U . . .
H18B H 0.519279 0.270962 0.082510 0.072 Uiso 1 1 calc R U . . .
H18C H 0.718941 0.217940 0.043162 0.072 Uiso 1 1 calc R U . . .
C19 C 0.5701(3) -0.0629(3) 0.20802(18) 0.0666(7) Uani 1 1 d . . . . .
H19A H 0.549451 -0.098782 0.142367 0.080 Uiso 1 1 calc R U . . .
H19B H 0.670612 -0.122425 0.225532 0.080 Uiso 1 1 calc R U . . .
H19C H 0.469701 -0.078165 0.269539 0.080 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.332(2) . ?
O1 B1 1.457(3) . ?
B1 F1 1.379(3) . ?
B1 F2 1.394(2) . ?
B1 N1 1.598(2) . ?
N1 C9 1.357(2) . ?
N1 C1 1.406(2) . ?
C1 C2 1.405(2) . ?
C1 C6 1.418(2) . ?
C2 C3 1.371(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.398(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.411(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.420(3) . ?
C7 C8 1.347(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.433(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.409(2) . ?
C10 C11 1.362(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.465(3) . ?
C12 C17 1.397(2) . ?
C12 C13 1.400(3) . ?
C13 C14 1.374(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.408(3) . ?
C14 H14A 0.9300 . ?
C15 N2 1.374(2) . ?
C15 C16 1.409(3) . ?
C16 C17 1.375(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
N2 C19 1.443(3) . ?
N2 C18 1.458(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C11 O1 B1 126.27(14) . . ?
F1 B1 F2 110.25(17) . . ?
F1 B1 O1 108.74(17) . . ?
F2 B1 O1 108.78(17) . . ?
F1 B1 N1 109.47(16) . . ?
F2 B1 N1 108.49(16) . . ?
O1 B1 N1 111.11(15) . . ?
C9 N1 C1 120.56(14) . . ?
C9 N1 B1 118.80(15) . . ?
C1 N1 B1 120.63(14) . . ?
C2 C1 N1 121.83(15) . . ?
C2 C1 C6 118.45(17) . . ?
N1 C1 C6 119.72(16) . . ?
C3 C2 C1 120.49(17) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 121.40(19) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 119.16(19) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 121.16(18) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 C1 119.33(17) . . ?
C5 C6 C7 121.83(16) . . ?
C1 C6 C7 118.83(17) . . ?
C8 C7 C6 120.11(16) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 121.13(17) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
N1 C9 C10 121.31(15) . . ?
N1 C9 C8 119.65(16) . . ?
C10 C9 C8 119.04(16) . . ?
C11 C10 C9 122.82(17) . . ?
C11 C10 H10A 118.6 . . ?
C9 C10 H10A 118.6 . . ?
O1 C11 C10 119.57(17) . . ?
O1 C11 C12 115.78(15) . . ?
C10 C11 C12 124.65(16) . . ?
C17 C12 C13 116.33(17) . . ?
C17 C12 C11 120.66(16) . . ?
C13 C12 C11 123.01(16) . . ?
C14 C13 C12 122.24(18) . . ?
C14 C13 H13A 118.9 . . ?
C12 C13 H13A 118.9 . . ?
C13 C14 C15 121.42(18) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
N2 C15 C14 121.65(17) . . ?
N2 C15 C16 122.03(17) . . ?
C14 C15 C16 116.32(17) . . ?
C17 C16 C15 121.55(17) . . ?
C17 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
C16 C17 C12 122.12(17) . . ?
C16 C17 H17A 118.9 . . ?
C12 C17 H17A 118.9 . . ?
C15 N2 C19 120.91(17) . . ?
C15 N2 C18 121.15(17) . . ?
C19 N2 C18 117.86(17) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 B1 F1 123.19(19) . . . . ?
C11 O1 B1 F2 -116.72(19) . . . . ?
C11 O1 B1 N1 2.6(3) . . . . ?
F1 B1 N1 C9 -123.99(17) . . . . ?
F2 B1 N1 C9 115.66(18) . . . . ?
O1 B1 N1 C9 -3.9(2) . . . . ?
F1 B1 N1 C1 57.1(2) . . . . ?
F2 B1 N1 C1 -63.3(2) . . . . ?
O1 B1 N1 C1 177.19(15) . . . . ?
C9 N1 C1 C2 178.77(16) . . . . ?
B1 N1 C1 C2 -2.3(3) . . . . ?
C9 N1 C1 C6 -0.5(3) . . . . ?
B1 N1 C1 C6 178.46(16) . . . . ?
N1 C1 C2 C3 -178.78(18) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 179.50(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C5 179.15(16) . . . . ?
C2 C1 C6 C7 -179.47(16) . . . . ?
N1 C1 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -179.17(18) . . . . ?
C1 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C1 N1 C9 C10 -178.46(16) . . . . ?
B1 N1 C9 C10 2.6(3) . . . . ?
C1 N1 C9 C8 1.1(3) . . . . ?
B1 N1 C9 C8 -177.80(16) . . . . ?
C7 C8 C9 N1 -1.2(3) . . . . ?
C7 C8 C9 C10 178.42(17) . . . . ?
N1 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -179.21(17) . . . . ?
B1 O1 C11 C10 0.1(3) . . . . ?
B1 O1 C11 C12 179.45(17) . . . . ?
C9 C10 C11 O1 -1.9(3) . . . . ?
C9 C10 C11 C12 178.79(16) . . . . ?
O1 C11 C12 C17 -0.3(3) . . . . ?
C10 C11 C12 C17 179.01(17) . . . . ?
O1 C11 C12 C13 179.51(17) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C11 C12 C13 C14 179.40(18) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 N2 -179.41(19) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
N2 C15 C16 C17 179.70(18) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C12 -0.4(3) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
C11 C12 C17 C16 -179.11(17) . . . . ?
C14 C15 N2 C19 179.5(2) . . . . ?
C16 C15 N2 C19 -0.7(3) . . . . ?
C14 C15 N2 C18 2.8(3) . . . . ?
C16 C15 N2 C18 -177.50(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A F1 0.93 2.38 2.943(2) 118.7 . yes
C2 H2A F2 0.93 2.56 3.068(2) 115.1 . yes

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_e1446a
_database_code_depnum_ccdc_archive 'CCDC 2090003'
loop_
_audit_author_name
_audit_author_address
'Andrzej Wojtczak'
;Nicolaus Copernicus University
Poland
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 B F2 N2 O'
_chemical_formula_sum            'C23 H19 B F2 N2 O'
_chemical_formula_weight         388.21

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

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

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

_cell_length_a                   7.4012(9)
_cell_length_b                   18.135(2)
_cell_length_c                   27.312(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3665.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2155
_cell_measurement_theta_min      2.2860
_cell_measurement_theta_max      26.5930

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_exptl_absorpt_special_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            11559
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.367
_diffrn_reflns_theta_max         28.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4213
_reflns_number_gt                1934
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB-2017 (Sheldrick, 2017)'
_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)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4213
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1564
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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
O1 O 0.5148(3) -0.00248(11) 0.09718(8) 0.0653(7) Uani 1 1 d . . . . .
B1 B 0.5695(5) 0.06557(18) 0.12035(13) 0.0449(9) Uani 1 1 d . . . . .
F1 F 0.4416(2) 0.11881(9) 0.11001(7) 0.0580(5) Uani 1 1 d . . . . .
F2 F 0.7349(2) 0.08560(10) 0.10045(6) 0.0617(6) Uani 1 1 d . . . . .
N1 N 0.5857(3) 0.05731(11) 0.17787(8) 0.0364(6) Uani 1 1 d . . . . .
C1 C 0.6411(4) 0.11857(14) 0.20606(11) 0.0367(7) Uani 1 1 d . . . . .
C2 C 0.6929(4) 0.18474(14) 0.18241(12) 0.0486(8) Uani 1 1 d . . . . .
H2A H 0.690435 0.188109 0.148440 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7470(4) 0.24409(15) 0.21028(14) 0.0524(9) Uani 1 1 d . . . . .
H3A H 0.778507 0.287916 0.194800 0.063 Uiso 1 1 calc R U . . .
C4 C 0.7553(4) 0.23992(16) 0.26053(13) 0.0512(9) Uani 1 1 d . . . . .
H4A H 0.794388 0.280257 0.278696 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7058(4) 0.17631(14) 0.28356(12) 0.0447(8) Uani 1 1 d . . . . .
H5A H 0.711429 0.173921 0.317540 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6470(4) 0.11464(14) 0.25735(11) 0.0354(7) Uani 1 1 d . . . . .
C7 C 0.5924(3) 0.04675(14) 0.28112(10) 0.0329(6) Uani 1 1 d . . . . .
C8 C 0.5854(4) 0.03973(15) 0.33273(11) 0.0422(7) Uani 1 1 d . . . . .
H8A H 0.613936 0.080093 0.352262 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5377(4) -0.02521(16) 0.35422(11) 0.0474(8) Uani 1 1 d . . . . .
H9A H 0.534517 -0.029052 0.388168 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4939(4) -0.08545(16) 0.32546(11) 0.0469(8) Uani 1 1 d . . . . .
H10A H 0.463343 -0.129940 0.340234 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4950(4) -0.08019(15) 0.27584(11) 0.0410(7) Uani 1 1 d . . . . .
H11A H 0.462970 -0.120898 0.257035 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5438(3) -0.01432(14) 0.25265(11) 0.0332(6) Uani 1 1 d . . . . .
C13 C 0.5428(3) -0.00734(14) 0.19918(11) 0.0333(7) Uani 1 1 d . . . . .
C14 C 0.4964(4) -0.06805(15) 0.16972(10) 0.0382(7) Uani 1 1 d . . . . .
H14A H 0.471526 -0.112645 0.185125 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4857(4) -0.06544(15) 0.12011(11) 0.0397(7) Uani 1 1 d . . . . .
C16 C 0.4490(4) -0.12798(15) 0.08867(10) 0.0401(7) Uani 1 1 d . . . . .
C17 C 0.4397(4) -0.12078(18) 0.03772(11) 0.0519(8) Uani 1 1 d . . . . .
H17A H 0.444778 -0.073842 0.024065 0.062 Uiso 1 1 calc R U . . .
C18 C 0.4233(5) -0.18036(17) 0.00726(11) 0.0535(9) Uani 1 1 d . . . . .
H18A H 0.418639 -0.172894 -0.026407 0.064 Uiso 1 1 calc R U . . .
C19 C 0.4135(4) -0.25203(17) 0.02562(11) 0.0444(8) Uani 1 1 d . . . . .
C20 C 0.4149(4) -0.25968(16) 0.07682(12) 0.0534(9) Uani 1 1 d . . . . .
H20A H 0.404997 -0.306408 0.090594 0.064 Uiso 1 1 calc R U . . .
C21 C 0.4306(4) -0.19948(15) 0.10675(10) 0.0471(8) Uani 1 1 d . . . . .
H21A H 0.428995 -0.206557 0.140470 0.057 Uiso 1 1 calc R U . . .
N2 N 0.4060(4) -0.31201(15) -0.00438(9) 0.0558(7) Uani 1 1 d . . . . .
C22 C 0.4139(5) -0.3047(2) -0.05690(11) 0.0692(11) Uani 1 1 d . . . . .
H22A H 0.406819 -0.352627 -0.071698 0.083 Uiso 1 1 calc R U . . .
H22B H 0.314485 -0.275032 -0.067945 0.083 Uiso 1 1 calc R U . . .
H22C H 0.525577 -0.281556 -0.066031 0.083 Uiso 1 1 calc R U . . .
C23 C 0.4056(6) -0.38653(18) 0.01539(13) 0.0740(11) Uani 1 1 d . . . . .
H23A H 0.399938 -0.421412 -0.011002 0.089 Uiso 1 1 calc R U . . .
H23B H 0.514157 -0.394490 0.033910 0.089 Uiso 1 1 calc R U . . .
H23C H 0.302567 -0.392853 0.036314 0.089 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.320(3) . ?
O1 B1 1.445(4) . ?
B1 F1 1.382(4) . ?
B1 F2 1.388(4) . ?
B1 N1 1.583(4) . ?
N1 C13 1.347(3) . ?
N1 C1 1.412(3) . ?
C1 C6 1.403(4) . ?
C1 C2 1.416(4) . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.364(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.449(3) . ?
C7 C12 1.400(4) . ?
C7 C8 1.416(4) . ?
C8 C9 1.363(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.384(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.359(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.399(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.466(4) . ?
C13 C14 1.406(4) . ?
C14 C15 1.358(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.448(4) . ?
C16 C21 1.394(4) . ?
C16 C17 1.399(4) . ?
C17 C18 1.369(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.395(4) . ?
C18 H18A 0.9300 . ?
C19 N2 1.363(4) . ?
C19 C20 1.405(4) . ?
C20 C21 1.369(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
N2 C22 1.442(4) . ?
N2 C23 1.455(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C15 O1 B1 125.2(3) . . ?
F1 B1 F2 110.0(2) . . ?
F1 B1 O1 108.4(3) . . ?
F2 B1 O1 107.4(3) . . ?
F1 B1 N1 108.7(3) . . ?
F2 B1 N1 110.3(3) . . ?
O1 B1 N1 112.0(2) . . ?
C13 N1 C1 121.2(2) . . ?
C13 N1 B1 119.6(2) . . ?
C1 N1 B1 119.2(2) . . ?
C6 C1 N1 120.9(2) . . ?
C6 C1 C2 119.4(3) . . ?
N1 C1 C2 119.8(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 122.5(3) . . ?
C1 C6 C7 118.8(3) . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 C6 119.6(3) . . ?
C8 C7 C6 122.2(3) . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 119.4(3) . . ?
C11 C12 C13 121.5(2) . . ?
C7 C12 C13 119.1(2) . . ?
N1 C13 C14 119.5(3) . . ?
N1 C13 C12 120.3(2) . . ?
C14 C13 C12 120.2(2) . . ?
C15 C14 C13 123.9(3) . . ?
C15 C14 H14A 118.0 . . ?
C13 C14 H14A 118.0 . . ?
O1 C15 C14 119.6(3) . . ?
O1 C15 C16 115.3(3) . . ?
C14 C15 C16 125.1(3) . . ?
C21 C16 C17 115.7(3) . . ?
C21 C16 C15 122.5(3) . . ?
C17 C16 C15 121.7(3) . . ?
C18 C17 C16 122.3(3) . . ?
C18 C17 H17A 118.8 . . ?
C16 C17 H17A 118.8 . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18A 119.3 . . ?
C19 C18 H18A 119.3 . . ?
N2 C19 C18 122.0(3) . . ?
N2 C19 C20 121.3(3) . . ?
C18 C19 C20 116.7(3) . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C16 122.6(3) . . ?
C20 C21 H21A 118.7 . . ?
C16 C21 H21A 118.7 . . ?
C19 N2 C22 121.5(3) . . ?
C19 N2 C23 121.2(3) . . ?
C22 N2 C23 117.0(3) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 O1 B1 F1 -121.8(3) . . . . ?
C15 O1 B1 F2 119.5(3) . . . . ?
C15 O1 B1 N1 -1.8(4) . . . . ?
F1 B1 N1 C13 117.2(3) . . . . ?
F2 B1 N1 C13 -122.1(3) . . . . ?
O1 B1 N1 C13 -2.5(4) . . . . ?
F1 B1 N1 C1 -61.4(3) . . . . ?
F2 B1 N1 C1 59.3(3) . . . . ?
O1 B1 N1 C1 178.9(2) . . . . ?
C13 N1 C1 C6 -2.3(4) . . . . ?
B1 N1 C1 C6 176.3(3) . . . . ?
C13 N1 C1 C2 177.2(2) . . . . ?
B1 N1 C1 C2 -4.2(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
N1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
N1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
N1 C1 C6 C7 -0.9(4) . . . . ?
C2 C1 C6 C7 179.6(2) . . . . ?
C5 C6 C7 C12 -176.7(2) . . . . ?
C1 C6 C7 C12 3.1(4) . . . . ?
C5 C6 C7 C8 3.6(4) . . . . ?
C1 C6 C7 C8 -176.6(3) . . . . ?
C12 C7 C8 C9 1.8(4) . . . . ?
C6 C7 C8 C9 -178.5(3) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C10 C11 C12 C13 -178.9(3) . . . . ?
C8 C7 C12 C11 -1.6(4) . . . . ?
C6 C7 C12 C11 178.6(2) . . . . ?
C8 C7 C12 C13 177.5(2) . . . . ?
C6 C7 C12 C13 -2.2(4) . . . . ?
C1 N1 C13 C14 -177.0(2) . . . . ?
B1 N1 C13 C14 4.4(4) . . . . ?
C1 N1 C13 C12 3.2(4) . . . . ?
B1 N1 C13 C12 -175.4(2) . . . . ?
C11 C12 C13 N1 178.2(2) . . . . ?
C7 C12 C13 N1 -0.9(4) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C7 C12 C13 C14 179.3(2) . . . . ?
N1 C13 C14 C15 -2.3(4) . . . . ?
C12 C13 C14 C15 177.5(3) . . . . ?
B1 O1 C15 C14 4.1(5) . . . . ?
B1 O1 C15 C16 -174.2(3) . . . . ?
C13 C14 C15 O1 -2.1(5) . . . . ?
C13 C14 C15 C16 176.1(3) . . . . ?
O1 C15 C16 C21 174.4(3) . . . . ?
C14 C15 C16 C21 -3.8(5) . . . . ?
O1 C15 C16 C17 -2.0(4) . . . . ?
C14 C15 C16 C17 179.8(3) . . . . ?
C21 C16 C17 C18 -3.4(5) . . . . ?
C15 C16 C17 C18 173.3(3) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 N2 -176.7(3) . . . . ?
C17 C18 C19 C20 2.1(5) . . . . ?
N2 C19 C20 C21 177.0(3) . . . . ?
C18 C19 C20 C21 -1.9(5) . . . . ?
C19 C20 C21 C16 -1.1(5) . . . . ?
C17 C16 C21 C20 3.7(5) . . . . ?
C15 C16 C21 C20 -173.0(3) . . . . ?
C18 C19 N2 C22 2.0(5) . . . . ?
C20 C19 N2 C22 -176.8(3) . . . . ?
C18 C19 N2 C23 176.7(3) . . . . ?
C20 C19 N2 C23 -2.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A F1 0.93 2.46 2.967(4) 114.0 . yes
C2 H2A F2 0.93 2.30 2.888(4) 120.9 . yes
C23 H23B F2 0.96 2.62 3.568(4) 167.9 8_755 yes

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_e1444a_a
_database_code_depnum_ccdc_archive 'CCDC 2090002'
loop_
_audit_author_name
_audit_author_address
'Andrzej Wojtczak'
;Nicolaus Copernicus University
Poland
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 B F2 N2 O'
_chemical_formula_sum            'C19 H17 B F2 N2 O'
_chemical_formula_weight         338.15

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

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

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

_cell_length_a                   30.6090(18)
_cell_length_b                   7.2702(5)
_cell_length_c                   44.556(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9915.3(10)
_cell_formula_units_Z            24
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3845
_cell_measurement_theta_min      2.6580
_cell_measurement_theta_max      22.4660

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             4224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_exptl_absorpt_special_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            52584
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_av_R_equivalents  0.1731
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         23.999
_diffrn_reflns_theta_full        23.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7780
_reflns_number_gt                3772
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB-2017 (Sheldrick, 2017)'
_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)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7780
_refine_ls_number_parameters     676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1835
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2093
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.61630(10) 0.9007(5) 0.60587(7) 0.0531(10) Uani 1 1 d . . . . .
B1 B 0.65090(19) 0.8863(9) 0.62816(13) 0.0489(16) Uani 1 1 d . . . . .
F1 F 0.64548(9) 0.7303(5) 0.64522(6) 0.0780(10) Uani 1 1 d . . . . .
F2 F 0.65030(9) 1.0396(5) 0.64614(6) 0.0825(11) Uani 1 1 d . . . . .
N1 N 0.69648(12) 0.8714(5) 0.61207(8) 0.0399(10) Uani 1 1 d . . . . .
C1 C 0.73340(17) 0.9129(6) 0.62838(10) 0.0473(14) Uani 1 1 d . . . . .
H1A H 0.730152 0.958761 0.647738 0.057 Uiso 1 1 calc R U . . .
C2 C 0.77377(16) 0.8897(6) 0.61748(11) 0.0480(14) Uani 1 1 d . . . . .
H2A H 0.797967 0.919060 0.629163 0.058 Uiso 1 1 calc R U . . .
C3 C 0.77936(15) 0.8207(6) 0.58830(10) 0.0376(12) Uani 1 1 d . . . . .
C4 C 0.82098(16) 0.7935(7) 0.57571(12) 0.0523(14) Uani 1 1 d . . . . .
H4A H 0.845703 0.821559 0.586946 0.063 Uiso 1 1 calc R U . . .
C5 C 0.82564(17) 0.7273(7) 0.54764(13) 0.0575(16) Uani 1 1 d . . . . .
H5A H 0.853394 0.711820 0.539537 0.069 Uiso 1 1 calc R U . . .
C6 C 0.78879(16) 0.6820(6) 0.53074(11) 0.0484(14) Uani 1 1 d . . . . .
H6A H 0.792169 0.634224 0.511521 0.058 Uiso 1 1 calc R U . . .
C7 C 0.74777(16) 0.7072(6) 0.54216(10) 0.0425(13) Uani 1 1 d . . . . .
H7A H 0.723461 0.678189 0.530573 0.051 Uiso 1 1 calc R U . . .
C8 C 0.74223(14) 0.7761(6) 0.57100(10) 0.0333(12) Uani 1 1 d . . . . .
C9 C 0.69969(14) 0.8050(6) 0.58363(11) 0.0369(12) Uani 1 1 d . . . . .
C10 C 0.66047(15) 0.7734(6) 0.56793(10) 0.0431(13) Uani 1 1 d . . . . .
H10A H 0.661813 0.714027 0.549464 0.052 Uiso 1 1 calc R U . . .
C11 C 0.62068(16) 0.8258(6) 0.57857(11) 0.0417(13) Uani 1 1 d . . . . .
C12 C 0.57985(16) 0.8104(7) 0.56171(11) 0.0441(13) Uani 1 1 d . . . . .
C13 C 0.57963(15) 0.7916(7) 0.53063(11) 0.0510(14) Uani 1 1 d . . . . .
H13A H 0.606188 0.793398 0.520504 0.061 Uiso 1 1 calc R U . . .
C14 C 0.54196(16) 0.7705(7) 0.51423(11) 0.0557(15) Uani 1 1 d . . . . .
H14A H 0.543539 0.759360 0.493468 0.067 Uiso 1 1 calc R U . . .
C15 C 0.50062(17) 0.7654(7) 0.52869(13) 0.0516(14) Uani 1 1 d . . . . .
C16 C 0.50089(16) 0.7895(7) 0.55967(13) 0.0596(16) Uani 1 1 d . . . . .
H16A H 0.474507 0.789474 0.570023 0.072 Uiso 1 1 calc R U . . .
C17 C 0.53911(17) 0.8131(7) 0.57537(11) 0.0577(15) Uani 1 1 d . . . . .
H17A H 0.537612 0.831709 0.595994 0.069 Uiso 1 1 calc R U . . .
N2 N 0.46314(14) 0.7338(6) 0.51281(11) 0.0663(14) Uani 1 1 d . . . . .
C18 C 0.46343(18) 0.7218(8) 0.48051(13) 0.0781(19) Uani 1 1 d . . . . .
H18A H 0.434302 0.699126 0.473415 0.117 Uiso 1 1 calc R U . . .
H18B H 0.473976 0.835293 0.472230 0.117 Uiso 1 1 calc R U . . .
H18C H 0.482187 0.622855 0.474368 0.117 Uiso 1 1 calc R U . . .
C19 C 0.42112(17) 0.7311(9) 0.52838(14) 0.095(2) Uani 1 1 d . . . . .
H19A H 0.398191 0.707326 0.514195 0.142 Uiso 1 1 calc R U . . .
H19B H 0.421340 0.636184 0.543355 0.142 Uiso 1 1 calc R U . . .
H19C H 0.416223 0.848023 0.537806 0.142 Uiso 1 1 calc R U . . .
N21 N 0.79773(12) 0.3853(5) 0.77997(8) 0.0389(10) Uani 1 1 d . . . . .
B21 B 0.84128(19) 0.3676(9) 0.79847(13) 0.0457(16) Uani 1 1 d . . . . .
F21 F 0.84052(9) 0.2118(5) 0.81515(7) 0.0820(11) Uani 1 1 d . . . . .
F22 F 0.84369(10) 0.5195(5) 0.81692(7) 0.0867(11) Uani 1 1 d . . . . .
O21 O 0.87779(10) 0.3611(5) 0.77830(7) 0.0590(10) Uani 1 1 d . . . . .
C21 C 0.75895(17) 0.3409(6) 0.79380(10) 0.0442(13) Uani 1 1 d . . . . .
H21A H 0.759965 0.290728 0.812985 0.053 Uiso 1 1 calc R U . . .
C22 C 0.72023(15) 0.3661(6) 0.78116(11) 0.0453(13) Uani 1 1 d . . . . .
H22A H 0.694831 0.333728 0.791325 0.054 Uiso 1 1 calc R U . . .
C23 C 0.71795(15) 0.4428(6) 0.75198(10) 0.0395(13) Uani 1 1 d . . . . .
C24 C 0.67730(16) 0.4732(7) 0.73709(12) 0.0526(15) Uani 1 1 d . . . . .
H24A H 0.651268 0.441742 0.746546 0.063 Uiso 1 1 calc R U . . .
C25 C 0.67648(16) 0.5476(7) 0.70932(12) 0.0542(15) Uani 1 1 d . . . . .
H25A H 0.649817 0.566415 0.699791 0.065 Uiso 1 1 calc R U . . .
C26 C 0.71502(16) 0.5965(6) 0.69475(11) 0.0480(14) Uani 1 1 d . . . . .
H26A H 0.713831 0.648969 0.675729 0.058 Uiso 1 1 calc R U . . .
C27 C 0.75463(15) 0.5680(6) 0.70820(10) 0.0391(12) Uani 1 1 d . . . . .
H27A H 0.780172 0.599464 0.698129 0.047 Uiso 1 1 calc R U . . .
C28 C 0.75699(15) 0.4916(6) 0.73708(10) 0.0359(12) Uani 1 1 d . . . . .
C29 C 0.79753(15) 0.4562(6) 0.75214(10) 0.0350(12) Uani 1 1 d . . . . .
C30 C 0.83880(16) 0.4877(7) 0.73829(10) 0.0427(13) Uani 1 1 d . . . . .
H30A H 0.839569 0.547152 0.719812 0.051 Uiso 1 1 calc R U . . .
C31 C 0.87686(16) 0.4346(7) 0.75097(11) 0.0445(14) Uani 1 1 d . . . . .
C32 C 0.91944(16) 0.4397(7) 0.73619(11) 0.0464(13) Uani 1 1 d . . . . .
C33 C 0.92589(16) 0.5277(7) 0.70909(12) 0.0597(16) Uani 1 1 d . . . . .
H33A H 0.902385 0.586845 0.700047 0.072 Uiso 1 1 calc R U . . .
C34 C 0.96598(18) 0.5309(8) 0.69496(12) 0.0663(17) Uani 1 1 d . . . . .
H34A H 0.969056 0.593972 0.676917 0.080 Uiso 1 1 calc R U . . .
C35 C 1.00216(16) 0.4405(7) 0.70742(12) 0.0524(14) Uani 1 1 d . . . . .
C36 C 0.99567(16) 0.3519(8) 0.73442(12) 0.0617(16) Uani 1 1 d . . . . .
H36A H 1.018956 0.290402 0.743324 0.074 Uiso 1 1 calc R U . . .
C37 C 0.95564(17) 0.3518(7) 0.74859(11) 0.0566(15) Uani 1 1 d . . . . .
H37A H 0.952714 0.291581 0.766888 0.068 Uiso 1 1 calc R U . . .
N22 N 1.04217(14) 0.4386(7) 0.69323(11) 0.0726(15) Uani 1 1 d . . . . .
C38 C 1.04999(18) 0.5388(10) 0.66632(14) 0.109(3) Uani 1 1 d . . . . .
H38A H 1.079633 0.519954 0.659996 0.163 Uiso 1 1 calc R U . . .
H38B H 1.030456 0.496590 0.650936 0.163 Uiso 1 1 calc R U . . .
H38C H 1.045151 0.667424 0.669884 0.163 Uiso 1 1 calc R U . . .
C39 C 1.07907(18) 0.3481(9) 0.70615(14) 0.096(2) Uani 1 1 d . . . . .
H39A H 1.103829 0.361473 0.693107 0.144 Uiso 1 1 calc R U . . .
H39B H 1.085560 0.402090 0.725302 0.144 Uiso 1 1 calc R U . . .
H39C H 1.072624 0.219825 0.708734 0.144 Uiso 1 1 calc R U . . .
N41 N 0.70551(12) -0.2582(5) 0.94588(8) 0.0366(10) Uani 1 1 d . . . . .
B41 B 0.6616(2) -0.2736(9) 0.96355(13) 0.0446(15) Uani 1 1 d . . . . .
F41 F 0.65993(9) -0.4386(4) 0.97829(6) 0.0656(9) Uani 1 1 d . . . . .
F42 F 0.66102(9) -0.1319(4) 0.98417(6) 0.0692(9) Uani 1 1 d . . . . .
O41 O 0.62491(10) -0.2584(5) 0.94355(7) 0.0569(10) Uani 1 1 d . . . . .
C41 C 0.74333(16) -0.3082(6) 0.96057(10) 0.0423(13) Uani 1 1 d . . . . .
H41A H 0.741247 -0.362354 0.979427 0.051 Uiso 1 1 calc R U . . .
C42 C 0.78310(16) -0.2815(6) 0.94857(10) 0.0420(13) Uani 1 1 d . . . . .
H42A H 0.807957 -0.315737 0.959192 0.050 Uiso 1 1 calc R U . . .
C43 C 0.78712(15) -0.2017(6) 0.91999(10) 0.0380(12) Uani 1 1 d . . . . .
C44 C 0.82835(16) -0.1695(7) 0.90668(11) 0.0491(14) Uani 1 1 d . . . . .
H44A H 0.853648 -0.200110 0.917097 0.059 Uiso 1 1 calc R U . . .
C45 C 0.83142(16) -0.0948(7) 0.87901(12) 0.0558(15) Uani 1 1 d . . . . .
H45A H 0.858722 -0.075523 0.870400 0.067 Uiso 1 1 calc R U . . .
C46 C 0.79382(17) -0.0466(7) 0.86338(11) 0.0508(14) Uani 1 1 d . . . . .
H46A H 0.796338 0.005242 0.844370 0.061 Uiso 1 1 calc R U . . .
C47 C 0.75316(16) -0.0738(6) 0.87539(10) 0.0441(13) Uani 1 1 d . . . . .
H47A H 0.728385 -0.039749 0.864655 0.053 Uiso 1 1 calc R U . . .
C48 C 0.74895(15) -0.1537(6) 0.90412(10) 0.0359(12) Uani 1 1 d . . . . .
C49 C 0.70704(14) -0.1841(6) 0.91820(10) 0.0345(12) Uani 1 1 d . . . . .
C50 C 0.66676(15) -0.1407(6) 0.90408(10) 0.0401(13) Uani 1 1 d . . . . .
H50A H 0.667337 -0.083657 0.885404 0.048 Uiso 1 1 calc R U . . .
C51 C 0.62720(15) -0.1794(6) 0.91678(11) 0.0403(12) Uani 1 1 d . . . . .
C52 C 0.58520(16) -0.1435(7) 0.90245(10) 0.0429(13) Uani 1 1 d . . . . .
C53 C 0.58109(16) -0.0344(7) 0.87717(12) 0.0549(15) Uani 1 1 d . . . . .
H53A H 0.606056 0.017474 0.868810 0.066 Uiso 1 1 calc R U . . .
C54 C 0.54101(16) 0.0001(7) 0.86392(11) 0.0592(16) Uani 1 1 d . . . . .
H54A H 0.539214 0.077585 0.847362 0.071 Uiso 1 1 calc R U . . .
C55 C 0.50325(16) -0.0817(7) 0.87544(12) 0.0515(14) Uani 1 1 d . . . . .
C56 C 0.50755(17) -0.1920(7) 0.90106(12) 0.0615(16) Uani 1 1 d . . . . .
H56A H 0.482877 -0.246705 0.909343 0.074 Uiso 1 1 calc R U . . .
C57 C 0.54719(17) -0.2203(7) 0.91401(11) 0.0575(15) Uani 1 1 d . . . . .
H57A H 0.548926 -0.293306 0.931105 0.069 Uiso 1 1 calc R U . . .
N42 N 0.46325(14) -0.0542(7) 0.86182(11) 0.0695(14) Uani 1 1 d . . . . .
C58 C 0.45900(18) 0.0627(10) 0.83613(14) 0.106(3) Uani 1 1 d . . . . .
H58A H 0.429030 0.065134 0.829790 0.159 Uiso 1 1 calc R U . . .
H58B H 0.468219 0.184934 0.841237 0.159 Uiso 1 1 calc R U . . .
H58C H 0.476895 0.016285 0.820139 0.159 Uiso 1 1 calc R U . . .
C59 C 0.42383(17) -0.1275(8) 0.87496(14) 0.090(2) Uani 1 1 d . . . . .
H59A H 0.399262 -0.095614 0.862627 0.135 Uiso 1 1 calc R U . . .
H59B H 0.426094 -0.258965 0.876328 0.135 Uiso 1 1 calc R U . . .
H59C H 0.419928 -0.076806 0.894673 0.135 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.339(5) . ?
O1 B1 1.456(6) . ?
B1 F2 1.373(6) . ?
B1 F1 1.376(7) . ?
B1 N1 1.573(6) . ?
N1 C9 1.360(5) . ?
N1 C1 1.377(5) . ?
C1 C2 1.338(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.404(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.406(6) . ?
C3 C8 1.411(6) . ?
C4 C5 1.348(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.396(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.367(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.390(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.434(6) . ?
C9 C10 1.408(6) . ?
C10 C11 1.361(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.462(6) . ?
C12 C17 1.388(6) . ?
C12 C13 1.391(6) . ?
C13 C14 1.374(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.420(6) . ?
C14 H14A 0.9300 . ?
C15 N2 1.367(6) . ?
C15 C16 1.391(6) . ?
C16 C17 1.374(6) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
N2 C18 1.442(6) . ?
N2 C19 1.462(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N21 C29 1.343(5) . ?
N21 C21 1.376(5) . ?
N21 B21 1.573(6) . ?
B21 F21 1.355(6) . ?
B21 F22 1.378(7) . ?
B21 O21 1.435(6) . ?
O21 C31 1.331(5) . ?
C21 C22 1.325(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.416(6) . ?
C22 H22A 0.9300 . ?
C23 C28 1.412(6) . ?
C23 C24 1.427(6) . ?
C24 C25 1.351(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.393(6) . ?
C25 H25A 0.9300 . ?
C26 C27 1.368(6) . ?
C26 H26A 0.9300 . ?
C27 C28 1.404(6) . ?
C27 H27A 0.9300 . ?
C28 C29 1.434(6) . ?
C29 C30 1.424(6) . ?
C30 C31 1.351(6) . ?
C30 H30A 0.9300 . ?
C31 C32 1.461(6) . ?
C32 C33 1.380(6) . ?
C32 C37 1.394(6) . ?
C33 C34 1.379(6) . ?
C33 H33A 0.9300 . ?
C34 C35 1.403(6) . ?
C34 H34A 0.9300 . ?
C35 N22 1.378(6) . ?
C35 C36 1.379(6) . ?
C36 C37 1.378(6) . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9300 . ?
N22 C38 1.423(6) . ?
N22 C39 1.429(6) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
N41 C49 1.347(5) . ?
N41 C41 1.379(5) . ?
N41 B41 1.562(6) . ?
B41 F41 1.369(6) . ?
B41 F42 1.380(6) . ?
B41 O41 1.438(6) . ?
O41 C51 1.326(5) . ?
C41 C42 1.343(6) . ?
C41 H41A 0.9300 . ?
C42 C43 1.405(6) . ?
C42 H42A 0.9300 . ?
C43 C48 1.409(6) . ?
C43 C44 1.414(6) . ?
C44 C45 1.351(6) . ?
C44 H44A 0.9300 . ?
C45 C46 1.390(6) . ?
C45 H45A 0.9300 . ?
C46 C47 1.369(6) . ?
C46 H46A 0.9300 . ?
C47 C48 1.412(6) . ?
C47 H47A 0.9300 . ?
C48 C49 1.445(6) . ?
C49 C50 1.419(6) . ?
C50 C51 1.366(6) . ?
C50 H50A 0.9300 . ?
C51 C52 1.459(6) . ?
C52 C53 1.383(6) . ?
C52 C57 1.390(6) . ?
C53 C54 1.384(6) . ?
C53 H53A 0.9300 . ?
C54 C55 1.397(6) . ?
C54 H54A 0.9300 . ?
C55 N42 1.381(6) . ?
C55 C56 1.401(6) . ?
C56 C57 1.359(6) . ?
C56 H56A 0.9300 . ?
C57 H57A 0.9300 . ?
N42 C58 1.431(6) . ?
N42 C59 1.443(6) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?

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
C11 O1 B1 121.2(4) . . ?
F2 B1 F1 110.2(5) . . ?
F2 B1 O1 109.3(5) . . ?
F1 B1 O1 110.4(5) . . ?
F2 B1 N1 109.5(5) . . ?
F1 B1 N1 107.6(4) . . ?
O1 B1 N1 109.8(4) . . ?
C9 N1 C1 120.7(4) . . ?
C9 N1 B1 120.9(4) . . ?
C1 N1 B1 118.2(4) . . ?
C2 C1 N1 122.6(5) . . ?
C2 C1 H1A 118.7 . . ?
N1 C1 H1A 118.7 . . ?
C1 C2 C3 119.6(5) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 C4 122.0(5) . . ?
C2 C3 C8 119.3(4) . . ?
C4 C3 C8 118.7(5) . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 120.6(5) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.3(5) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C7 C8 C3 119.3(4) . . ?
C7 C8 C9 121.8(4) . . ?
C3 C8 C9 118.9(4) . . ?
N1 C9 C10 117.3(4) . . ?
N1 C9 C8 118.9(4) . . ?
C10 C9 C8 123.7(4) . . ?
C11 C10 C9 123.0(5) . . ?
C11 C10 H10A 118.5 . . ?
C9 C10 H10A 118.5 . . ?
O1 C11 C10 121.3(4) . . ?
O1 C11 C12 114.3(4) . . ?
C10 C11 C12 124.4(5) . . ?
C17 C12 C13 115.7(5) . . ?
C17 C12 C11 122.8(5) . . ?
C13 C12 C11 121.5(4) . . ?
C14 C13 C12 123.0(5) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
N2 C15 C16 122.7(5) . . ?
N2 C15 C14 121.1(5) . . ?
C16 C15 C14 116.2(5) . . ?
C17 C16 C15 121.7(5) . . ?
C17 C16 H16A 119.1 . . ?
C15 C16 H16A 119.1 . . ?
C16 C17 C12 122.7(5) . . ?
C16 C17 H17A 118.7 . . ?
C12 C17 H17A 118.7 . . ?
C15 N2 C18 121.5(5) . . ?
C15 N2 C19 119.7(5) . . ?
C18 N2 C19 118.6(5) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C29 N21 C21 120.0(4) . . ?
C29 N21 B21 121.3(4) . . ?
C21 N21 B21 118.5(4) . . ?
F21 B21 F22 110.1(5) . . ?
F21 B21 O21 109.2(5) . . ?
F22 B21 O21 111.0(5) . . ?
F21 B21 N21 109.9(5) . . ?
F22 B21 N21 107.0(4) . . ?
O21 B21 N21 109.6(4) . . ?
C31 O21 B21 122.9(4) . . ?
C22 C21 N21 123.3(5) . . ?
C22 C21 H21A 118.3 . . ?
N21 C21 H21A 118.3 . . ?
C21 C22 C23 119.3(4) . . ?
C21 C22 H22A 120.4 . . ?
C23 C22 H22A 120.4 . . ?
C28 C23 C22 119.2(4) . . ?
C28 C23 C24 118.7(5) . . ?
C22 C23 C24 122.0(5) . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C24 C25 C26 120.9(5) . . ?
C24 C25 H25A 119.6 . . ?
C26 C25 H25A 119.6 . . ?
C27 C26 C25 120.5(5) . . ?
C27 C26 H26A 119.7 . . ?
C25 C26 H26A 119.7 . . ?
C26 C27 C28 120.5(5) . . ?
C26 C27 H27A 119.8 . . ?
C28 C27 H27A 119.8 . . ?
C27 C28 C23 119.1(4) . . ?
C27 C28 C29 123.0(4) . . ?
C23 C28 C29 117.9(4) . . ?
N21 C29 C30 117.3(4) . . ?
N21 C29 C28 120.3(4) . . ?
C30 C29 C28 122.4(4) . . ?
C31 C30 C29 122.5(4) . . ?
C31 C30 H30A 118.7 . . ?
C29 C30 H30A 118.7 . . ?
O21 C31 C30 121.1(4) . . ?
O21 C31 C32 113.8(4) . . ?
C30 C31 C32 125.0(5) . . ?
C33 C32 C37 116.5(5) . . ?
C33 C32 C31 122.3(5) . . ?
C37 C32 C31 121.3(5) . . ?
C34 C33 C32 122.3(5) . . ?
C34 C33 H33A 118.8 . . ?
C32 C33 H33A 118.8 . . ?
C33 C34 C35 120.9(5) . . ?
C33 C34 H34A 119.5 . . ?
C35 C34 H34A 119.5 . . ?
N22 C35 C36 121.6(5) . . ?
N22 C35 C34 121.6(5) . . ?
C36 C35 C34 116.8(5) . . ?
C37 C36 C35 121.8(5) . . ?
C37 C36 H36A 119.1 . . ?
C35 C36 H36A 119.1 . . ?
C36 C37 C32 121.7(5) . . ?
C36 C37 H37A 119.2 . . ?
C32 C37 H37A 119.2 . . ?
C35 N22 C38 122.1(5) . . ?
C35 N22 C39 121.5(5) . . ?
C38 N22 C39 116.3(5) . . ?
N22 C38 H38A 109.5 . . ?
N22 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N22 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N22 C39 H39A 109.5 . . ?
N22 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N22 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C49 N41 C41 120.7(4) . . ?
C49 N41 B41 121.3(4) . . ?
C41 N41 B41 117.7(4) . . ?
F41 B41 F42 109.5(5) . . ?
F41 B41 O41 109.6(5) . . ?
F42 B41 O41 110.2(5) . . ?
F41 B41 N41 109.7(4) . . ?
F42 B41 N41 107.0(4) . . ?
O41 B41 N41 110.8(4) . . ?
C51 O41 B41 123.3(4) . . ?
C42 C41 N41 122.3(4) . . ?
C42 C41 H41A 118.9 . . ?
N41 C41 H41A 118.9 . . ?
C41 C42 C43 120.0(5) . . ?
C41 C42 H42A 120.0 . . ?
C43 C42 H42A 120.0 . . ?
C42 C43 C48 119.0(4) . . ?
C42 C43 C44 121.8(5) . . ?
C48 C43 C44 119.2(4) . . ?
C45 C44 C43 120.8(5) . . ?
C45 C44 H44A 119.6 . . ?
C43 C44 H44A 119.6 . . ?
C44 C45 C46 120.1(5) . . ?
C44 C45 H45A 120.0 . . ?
C46 C45 H45A 120.0 . . ?
C47 C46 C45 121.4(5) . . ?
C47 C46 H46A 119.3 . . ?
C45 C46 H46A 119.3 . . ?
C46 C47 C48 119.8(5) . . ?
C46 C47 H47A 120.1 . . ?
C48 C47 H47A 120.1 . . ?
C43 C48 C47 118.8(4) . . ?
C43 C48 C49 118.7(4) . . ?
C47 C48 C49 122.5(4) . . ?
N41 C49 C50 117.7(4) . . ?
N41 C49 C48 119.3(4) . . ?
C50 C49 C48 123.0(4) . . ?
C51 C50 C49 122.7(4) . . ?
C51 C50 H50A 118.6 . . ?
C49 C50 H50A 118.6 . . ?
O41 C51 C50 120.6(4) . . ?
O41 C51 C52 115.1(4) . . ?
C50 C51 C52 124.3(4) . . ?
C53 C52 C57 117.1(5) . . ?
C53 C52 C51 122.6(5) . . ?
C57 C52 C51 120.2(4) . . ?
C52 C53 C54 122.1(5) . . ?
C52 C53 H53A 118.9 . . ?
C54 C53 H53A 118.9 . . ?
C53 C54 C55 120.0(5) . . ?
C53 C54 H54A 120.0 . . ?
C55 C54 H54A 120.0 . . ?
N42 C55 C54 120.7(5) . . ?
N42 C55 C56 121.6(5) . . ?
C54 C55 C56 117.7(5) . . ?
C57 C56 C55 121.1(5) . . ?
C57 C56 H56A 119.5 . . ?
C55 C56 H56A 119.5 . . ?
C56 C57 C52 122.0(5) . . ?
C56 C57 H57A 119.0 . . ?
C52 C57 H57A 119.0 . . ?
C55 N42 C58 121.2(5) . . ?
C55 N42 C59 120.6(5) . . ?
C58 N42 C59 117.9(5) . . ?
N42 C58 H58A 109.5 . . ?
N42 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N42 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N42 C59 H59A 109.5 . . ?
N42 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
N42 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 B1 F2 148.7(4) . . . . ?
C11 O1 B1 F1 -89.9(5) . . . . ?
C11 O1 B1 N1 28.6(7) . . . . ?
F2 B1 N1 C9 -144.9(4) . . . . ?
F1 B1 N1 C9 95.3(5) . . . . ?
O1 B1 N1 C9 -24.9(6) . . . . ?
F2 B1 N1 C1 40.4(6) . . . . ?
F1 B1 N1 C1 -79.4(6) . . . . ?
O1 B1 N1 C1 160.4(4) . . . . ?
C9 N1 C1 C2 -0.4(7) . . . . ?
B1 N1 C1 C2 174.3(5) . . . . ?
N1 C1 C2 C3 0.1(7) . . . . ?
C1 C2 C3 C4 -180.0(5) . . . . ?
C1 C2 C3 C8 -0.3(7) . . . . ?
C2 C3 C4 C5 -179.9(5) . . . . ?
C8 C3 C4 C5 0.4(7) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C4 C5 C6 C7 1.2(8) . . . . ?
C5 C6 C7 C8 -0.9(7) . . . . ?
C6 C7 C8 C3 0.4(7) . . . . ?
C6 C7 C8 C9 179.7(4) . . . . ?
C2 C3 C8 C7 -179.8(4) . . . . ?
C4 C3 C8 C7 -0.1(6) . . . . ?
C2 C3 C8 C9 0.8(6) . . . . ?
C4 C3 C8 C9 -179.5(4) . . . . ?
C1 N1 C9 C10 -177.3(4) . . . . ?
B1 N1 C9 C10 8.1(6) . . . . ?
C1 N1 C9 C8 0.9(6) . . . . ?
B1 N1 C9 C8 -173.6(4) . . . . ?
C7 C8 C9 N1 179.5(4) . . . . ?
C3 C8 C9 N1 -1.1(6) . . . . ?
C7 C8 C9 C10 -2.4(7) . . . . ?
C3 C8 C9 C10 177.0(4) . . . . ?
N1 C9 C10 C11 7.8(7) . . . . ?
C8 C9 C10 C11 -170.3(4) . . . . ?
B1 O1 C11 C10 -16.1(7) . . . . ?
B1 O1 C11 C12 165.1(4) . . . . ?
C9 C10 C11 O1 -4.5(7) . . . . ?
C9 C10 C11 C12 174.2(4) . . . . ?
O1 C11 C12 C17 -20.6(7) . . . . ?
C10 C11 C12 C17 160.7(5) . . . . ?
O1 C11 C12 C13 159.6(4) . . . . ?
C10 C11 C12 C13 -19.2(8) . . . . ?
C17 C12 C13 C14 -2.2(7) . . . . ?
C11 C12 C13 C14 177.7(5) . . . . ?
C12 C13 C14 C15 -0.5(8) . . . . ?
C13 C14 C15 N2 -176.1(5) . . . . ?
C13 C14 C15 C16 2.2(8) . . . . ?
N2 C15 C16 C17 177.1(5) . . . . ?
C14 C15 C16 C17 -1.2(8) . . . . ?
C15 C16 C17 C12 -1.6(9) . . . . ?
C13 C12 C17 C16 3.2(8) . . . . ?
C11 C12 C17 C16 -176.7(5) . . . . ?
C16 C15 N2 C18 175.8(5) . . . . ?
C14 C15 N2 C18 -6.0(8) . . . . ?
C16 C15 N2 C19 2.3(8) . . . . ?
C14 C15 N2 C19 -179.5(5) . . . . ?
C29 N21 B21 F21 -144.0(4) . . . . ?
C21 N21 B21 F21 41.4(6) . . . . ?
C29 N21 B21 F22 96.4(5) . . . . ?
C21 N21 B21 F22 -78.1(5) . . . . ?
C29 N21 B21 O21 -24.0(7) . . . . ?
C21 N21 B21 O21 161.5(4) . . . . ?
F21 B21 O21 C31 146.2(4) . . . . ?
F22 B21 O21 C31 -92.2(6) . . . . ?
N21 B21 O21 C31 25.7(7) . . . . ?
C29 N21 C21 C22 -0.7(7) . . . . ?
B21 N21 C21 C22 173.9(5) . . . . ?
N21 C21 C22 C23 -0.2(7) . . . . ?
C21 C22 C23 C28 -0.3(7) . . . . ?
C21 C22 C23 C24 179.9(5) . . . . ?
C28 C23 C24 C25 -0.1(7) . . . . ?
C22 C23 C24 C25 179.7(5) . . . . ?
C23 C24 C25 C26 -0.2(8) . . . . ?
C24 C25 C26 C27 0.8(8) . . . . ?
C25 C26 C27 C28 -1.0(7) . . . . ?
C26 C27 C28 C23 0.6(7) . . . . ?
C26 C27 C28 C29 179.1(4) . . . . ?
C22 C23 C28 C27 -179.9(4) . . . . ?
C24 C23 C28 C27 -0.1(6) . . . . ?
C22 C23 C28 C29 1.6(6) . . . . ?
C24 C23 C28 C29 -178.6(4) . . . . ?
C21 N21 C29 C30 -175.9(4) . . . . ?
B21 N21 C29 C30 9.6(6) . . . . ?
C21 N21 C29 C28 2.0(6) . . . . ?
B21 N21 C29 C28 -172.4(4) . . . . ?
C27 C28 C29 N21 179.0(4) . . . . ?
C23 C28 C29 N21 -2.5(6) . . . . ?
C27 C28 C29 C30 -3.1(7) . . . . ?
C23 C28 C29 C30 175.4(4) . . . . ?
N21 C29 C30 C31 5.9(7) . . . . ?
C28 C29 C30 C31 -172.1(4) . . . . ?
B21 O21 C31 C30 -13.4(7) . . . . ?
B21 O21 C31 C32 170.3(5) . . . . ?
C29 C30 C31 O21 -4.8(8) . . . . ?
C29 C30 C31 C32 171.0(4) . . . . ?
O21 C31 C32 C33 -173.2(5) . . . . ?
C30 C31 C32 C33 10.6(8) . . . . ?
O21 C31 C32 C37 8.2(7) . . . . ?
C30 C31 C32 C37 -168.0(5) . . . . ?
C37 C32 C33 C34 -0.6(8) . . . . ?
C31 C32 C33 C34 -179.3(5) . . . . ?
C32 C33 C34 C35 1.3(9) . . . . ?
C33 C34 C35 N22 178.4(5) . . . . ?
C33 C34 C35 C36 -1.0(8) . . . . ?
N22 C35 C36 C37 -179.4(5) . . . . ?
C34 C35 C36 C37 0.0(8) . . . . ?
C35 C36 C37 C32 0.7(9) . . . . ?
C33 C32 C37 C36 -0.4(8) . . . . ?
C31 C32 C37 C36 178.3(5) . . . . ?
C36 C35 N22 C38 -176.1(6) . . . . ?
C34 C35 N22 C38 4.6(9) . . . . ?
C36 C35 N22 C39 -1.4(9) . . . . ?
C34 C35 N22 C39 179.3(6) . . . . ?
C49 N41 B41 F41 140.0(4) . . . . ?
C41 N41 B41 F41 -45.5(6) . . . . ?
C49 N41 B41 F42 -101.2(5) . . . . ?
C41 N41 B41 F42 73.2(5) . . . . ?
C49 N41 B41 O41 18.9(6) . . . . ?
C41 N41 B41 O41 -166.6(4) . . . . ?
F41 B41 O41 C51 -143.1(4) . . . . ?
F42 B41 O41 C51 96.3(5) . . . . ?
N41 B41 O41 C51 -21.9(7) . . . . ?
C49 N41 C41 C42 1.8(7) . . . . ?
B41 N41 C41 C42 -172.6(4) . . . . ?
N41 C41 C42 C43 -0.6(7) . . . . ?
C41 C42 C43 C48 -1.0(7) . . . . ?
C41 C42 C43 C44 179.4(4) . . . . ?
C42 C43 C44 C45 179.2(5) . . . . ?
C48 C43 C44 C45 -0.4(7) . . . . ?
C43 C44 C45 C46 0.7(8) . . . . ?
C44 C45 C46 C47 -0.3(8) . . . . ?
C45 C46 C47 C48 -0.5(7) . . . . ?
C42 C43 C48 C47 -179.9(4) . . . . ?
C44 C43 C48 C47 -0.3(7) . . . . ?
C42 C43 C48 C49 1.5(6) . . . . ?
C44 C43 C48 C49 -178.8(4) . . . . ?
C46 C47 C48 C43 0.8(7) . . . . ?
C46 C47 C48 C49 179.3(4) . . . . ?
C41 N41 C49 C50 178.3(4) . . . . ?
B41 N41 C49 C50 -7.5(6) . . . . ?
C41 N41 C49 C48 -1.2(6) . . . . ?
B41 N41 C49 C48 173.0(4) . . . . ?
C43 C48 C49 N41 -0.4(6) . . . . ?
C47 C48 C49 N41 -178.9(4) . . . . ?
C43 C48 C49 C50 -179.9(4) . . . . ?
C47 C48 C49 C50 1.6(7) . . . . ?
N41 C49 C50 C51 -3.3(7) . . . . ?
C48 C49 C50 C51 176.2(4) . . . . ?
B41 O41 C51 C50 13.5(7) . . . . ?
B41 O41 C51 C52 -168.0(4) . . . . ?
C49 C50 C51 O41 0.9(7) . . . . ?
C49 C50 C51 C52 -177.5(4) . . . . ?
O41 C51 C52 C53 168.5(5) . . . . ?
C50 C51 C52 C53 -13.0(8) . . . . ?
O41 C51 C52 C57 -11.7(7) . . . . ?
C50 C51 C52 C57 166.7(5) . . . . ?
C57 C52 C53 C54 0.8(8) . . . . ?
C51 C52 C53 C54 -179.4(5) . . . . ?
C52 C53 C54 C55 -2.3(8) . . . . ?
C53 C54 C55 N42 -177.6(5) . . . . ?
C53 C54 C55 C56 2.2(8) . . . . ?
N42 C55 C56 C57 179.0(5) . . . . ?
C54 C55 C56 C57 -0.8(8) . . . . ?
C55 C56 C57 C52 -0.6(9) . . . . ?
C53 C52 C57 C56 0.6(8) . . . . ?
C51 C52 C57 C56 -179.1(5) . . . . ?
C54 C55 N42 C58 -1.8(8) . . . . ?
C56 C55 N42 C58 178.3(5) . . . . ?
C54 C55 N42 C59 -175.4(5) . . . . ?
C56 C55 N42 C59 4.7(8) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
