# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_bww17164
_database_code_depnum_ccdc_archive 'CCDC 1574740'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2017-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 B F2 N O3'
_chemical_formula_sum            'C24 H20 B F2 N O3'
_chemical_formula_weight         419.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.151(2)
_cell_length_b                   13.828(3)
_cell_length_c                   13.934(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.20(3)
_cell_angle_gamma                90
_cell_volume                     1989.2(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6267
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.4726
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13400
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.159
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3879
_reflns_number_total             4488
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0962
_refine_ls_restrained_S_all      1.238
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+2.3050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.1853
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.20318(18) 0.46399(14) 0.67931(16) 0.0455(5) Uani 1 1 d . . . . .
F2 F 0.34697(19) 0.50530(14) 0.83816(17) 0.0499(5) Uani 1 1 d . . . . .
O1 O 0.3879(2) 0.36982(15) 0.75929(19) 0.0400(6) Uani 1 1 d . . . . .
O2 O 0.2124(2) 0.37374(14) 0.82305(18) 0.0365(5) Uani 1 1 d . . . . .
O3 O -0.1563(2) 0.10104(17) 0.95051(19) 0.0433(6) Uani 1 1 d . . . . .
N1 N 0.7664(2) 0.10697(18) 0.6453(2) 0.0333(6) Uani 1 1 d . . . . .
C1 C 0.8213(3) 0.1896(2) 0.6211(2) 0.0314(6) Uani 1 1 d . . . . .
C2 C 0.9257(3) 0.1959(3) 0.5891(2) 0.0388(7) Uani 1 1 d . . . . .
H2 H 0.9692 0.1399 0.5794 0.047 Uiso 1 1 calc R . . . .
C3 C 0.9625(3) 0.2875(3) 0.5723(3) 0.0428(8) Uani 1 1 d . . . . .
H3 H 1.0329 0.2944 0.5503 0.051 Uiso 1 1 calc R . . . .
C4 C 0.8999(3) 0.3706(3) 0.5866(3) 0.0412(8) Uani 1 1 d . . . . .
H4 H 0.9288 0.4325 0.5749 0.049 Uiso 1 1 calc R . . . .
C5 C 0.7958(3) 0.3631(2) 0.6176(2) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.7523 0.4194 0.6266 0.042 Uiso 1 1 calc R . . . .
C6 C 0.7566(3) 0.2723(2) 0.6353(2) 0.0294(6) Uani 1 1 d . . . . .
C7 C 0.6549(3) 0.2373(2) 0.6680(2) 0.0280(6) Uani 1 1 d . . . . .
C8 C 0.5610(3) 0.2823(2) 0.6947(2) 0.0279(6) Uani 1 1 d . . . . .
H8 H 0.5542 0.3508 0.6930 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4759(3) 0.2262(2) 0.7243(2) 0.0296(6) Uani 1 1 d . . . . .
C10 C 0.4875(3) 0.1243(2) 0.7266(2) 0.0316(6) Uani 1 1 d . . . . .
H10 H 0.4290 0.0867 0.7461 0.038 Uiso 1 1 calc R . . . .
C11 C 0.5807(3) 0.0778(2) 0.7016(2) 0.0326(7) Uani 1 1 d . . . . .
H11 H 0.5872 0.0093 0.7036 0.039 Uiso 1 1 calc R . . . .
C12 C 0.6658(3) 0.1346(2) 0.6729(2) 0.0295(6) Uani 1 1 d . . . . .
C13 C 0.8079(3) 0.0078(2) 0.6404(3) 0.0416(8) Uani 1 1 d . . . . .
H13A H 0.7867 -0.0320 0.6909 0.050 Uiso 1 1 calc R . . . .
H13B H 0.9031 0.0068 0.6608 0.050 Uiso 1 1 calc R . . . .
C14 C 0.7457(5) -0.0356(3) 0.5354(3) 0.0650(12) Uani 1 1 d . . . . .
H14A H 0.7596 0.0066 0.4841 0.097 Uiso 1 1 calc GR . . . .
H14B H 0.6525 -0.0428 0.5187 0.097 Uiso 1 1 calc GR . . . .
H14C H 0.7839 -0.0992 0.5343 0.097 Uiso 1 1 calc GR . . . .
C15 C 0.3788(3) 0.2747(2) 0.7540(2) 0.0277(6) Uani 1 1 d . . . . .
C16 C 0.2851(3) 0.2274(2) 0.7788(2) 0.0304(6) Uani 1 1 d . . . . .
H16 H 0.2749 0.1594 0.7698 0.036 Uiso 1 1 calc R . . . .
C17 C 0.2058(3) 0.2793(2) 0.8169(2) 0.0287(6) Uani 1 1 d . . . . .
C18 C 0.1122(3) 0.2340(2) 0.8531(2) 0.0274(6) Uani 1 1 d . . . . .
C19 C 0.1058(3) 0.1331(2) 0.8622(3) 0.0356(7) Uani 1 1 d . . . . .
H19 H 0.1646 0.0930 0.8458 0.043 Uiso 1 1 calc R . . . .
C20 C 0.0154(3) 0.0918(2) 0.8947(3) 0.0372(7) Uani 1 1 d . . . . .
H20 H 0.0122 0.0235 0.9009 0.045 Uiso 1 1 calc R . . . .
C21 C -0.0711(3) 0.1496(2) 0.9184(2) 0.0325(7) Uani 1 1 d . . . . .
C22 C -0.0667(3) 0.2498(2) 0.9107(2) 0.0323(7) Uani 1 1 d . . . . .
H22 H -0.1258 0.2894 0.9272 0.039 Uiso 1 1 calc R . . . .
C23 C 0.0259(3) 0.2910(2) 0.8785(2) 0.0320(6) Uani 1 1 d . . . . .
H23 H 0.0301 0.3594 0.8737 0.038 Uiso 1 1 calc R . . . .
C24 C -0.2503(3) 0.1563(3) 0.9743(3) 0.0436(8) Uani 1 1 d . . . . .
H24A H -0.3039 0.1931 0.9130 0.065 Uiso 1 1 calc GR . . . .
H24B H -0.2057 0.2011 1.0312 0.065 Uiso 1 1 calc GR . . . .
H24C H -0.3053 0.1126 0.9951 0.065 Uiso 1 1 calc GR . . . .
B1 B 0.2876(3) 0.4300(3) 0.7745(3) 0.0350(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
F1 B1 1.387(4) . ?
F2 B1 1.366(4) . ?
O1 C15 1.319(3) . ?
O1 B1 1.473(4) . ?
O2 C17 1.310(3) . ?
O2 B1 1.480(4) . ?
O3 C21 1.370(4) . ?
O3 C24 1.433(4) . ?
N1 C1 1.396(4) . ?
N1 C12 1.370(4) . ?
N1 C13 1.456(4) . ?
C1 C2 1.399(4) . ?
C1 C6 1.406(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C6 C7 1.455(4) . ?
C7 C8 1.384(4) . ?
C7 C12 1.425(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.402(4) . ?
C9 C10 1.415(4) . ?
C9 C15 1.459(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.402(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.489(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(4) . ?
C17 C18 1.460(4) . ?
C18 C19 1.406(4) . ?
C18 C23 1.388(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(4) . ?
C21 C22 1.391(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.394(4) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 B1 121.7(2) . . ?
C17 O2 B1 121.5(2) . . ?
C21 O3 C24 118.1(3) . . ?
C1 N1 C13 125.7(3) . . ?
C12 N1 C1 108.6(2) . . ?
C12 N1 C13 125.7(3) . . ?
N1 C1 C2 128.5(3) . . ?
N1 C1 C6 109.7(2) . . ?
C2 C1 C6 121.8(3) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.7(3) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.0(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 134.0(3) . . ?
C8 C7 C6 133.9(3) . . ?
C8 C7 C12 119.6(3) . . ?
C12 C7 C6 106.5(2) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 C15 119.1(3) . . ?
C10 C9 C15 121.5(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.1(3) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 118.0(3) . . ?
C12 C11 H11 121.0 . . ?
N1 C12 C7 109.2(2) . . ?
N1 C12 C11 129.7(3) . . ?
C11 C12 C7 121.1(3) . . ?
N1 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
N1 C13 C14 112.8(3) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C9 115.1(2) . . ?
O1 C15 C16 120.4(3) . . ?
C16 C15 C9 124.4(3) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
O2 C17 C16 120.7(3) . . ?
O2 C17 C18 115.8(2) . . ?
C16 C17 C18 123.5(3) . . ?
C19 C18 C17 121.6(3) . . ?
C23 C18 C17 120.0(3) . . ?
C23 C18 C19 118.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
O3 C21 C20 115.2(3) . . ?
O3 C21 C22 124.2(3) . . ?
C20 C21 C22 120.6(3) . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.0(3) . . ?
C23 C22 H22 120.5 . . ?
C18 C23 C22 121.3(3) . . ?
C18 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
F1 B1 O1 109.3(3) . . ?
F1 B1 O2 108.6(3) . . ?
F2 B1 F1 110.5(3) . . ?
F2 B1 O1 108.4(3) . . ?
F2 B1 O2 108.9(3) . . ?
O1 B1 O2 111.1(3) . . ?

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
O1 C15 C16 C17 -4.8(4) . . . . ?
O2 C17 C18 C19 -172.4(3) . . . . ?
O2 C17 C18 C23 8.2(4) . . . . ?
O3 C21 C22 C23 179.1(3) . . . . ?
N1 C1 C2 C3 -178.6(3) . . . . ?
N1 C1 C6 C5 178.9(3) . . . . ?
N1 C1 C6 C7 -1.1(3) . . . . ?
C1 N1 C12 C7 -0.7(3) . . . . ?
C1 N1 C12 C11 178.8(3) . . . . ?
C1 N1 C13 C14 -86.3(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C6 C7 C8 179.2(3) . . . . ?
C1 C6 C7 C12 0.7(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 -0.9(6) . . . . ?
C5 C6 C7 C12 -179.4(3) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C6 C7 C12 N1 0.0(3) . . . . ?
C6 C7 C12 C11 -179.5(3) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C9 C15 178.9(3) . . . . ?
C8 C7 C12 N1 -178.8(2) . . . . ?
C8 C7 C12 C11 1.7(4) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C8 C9 C15 O1 -6.0(4) . . . . ?
C8 C9 C15 C16 176.1(3) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C15 C16 C17 173.0(3) . . . . ?
C10 C9 C15 O1 172.8(3) . . . . ?
C10 C9 C15 C16 -5.1(4) . . . . ?
C10 C11 C12 N1 179.5(3) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
C12 N1 C1 C2 -179.9(3) . . . . ?
C12 N1 C1 C6 1.2(3) . . . . ?
C12 N1 C13 C14 92.7(4) . . . . ?
C12 C7 C8 C9 -1.2(4) . . . . ?
C13 N1 C1 C2 -0.8(5) . . . . ?
C13 N1 C1 C6 -179.7(3) . . . . ?
C13 N1 C12 C7 -179.8(3) . . . . ?
C13 N1 C12 C11 -0.4(5) . . . . ?
C15 O1 B1 F1 -97.2(3) . . . . ?
C15 O1 B1 F2 142.3(3) . . . . ?
C15 O1 B1 O2 22.7(4) . . . . ?
C15 C9 C10 C11 -178.2(3) . . . . ?
C15 C16 C17 O2 4.8(4) . . . . ?
C15 C16 C17 C18 -174.6(3) . . . . ?
C16 C17 C18 C19 7.0(4) . . . . ?
C16 C17 C18 C23 -172.4(3) . . . . ?
C17 O2 B1 F1 97.7(3) . . . . ?
C17 O2 B1 F2 -142.0(3) . . . . ?
C17 O2 B1 O1 -22.6(4) . . . . ?
C17 C18 C19 C20 -178.8(3) . . . . ?
C17 C18 C23 C22 178.3(3) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C18 C23 C22 -1.0(4) . . . . ?
C19 C20 C21 O3 -179.6(3) . . . . ?
C19 C20 C21 C22 -0.6(5) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C18 0.7(4) . . . . ?
C23 C18 C19 C20 0.6(5) . . . . ?
C24 O3 C21 C20 -178.8(3) . . . . ?
C24 O3 C21 C22 2.3(4) . . . . ?
B1 O1 C15 C9 171.8(3) . . . . ?
B1 O1 C15 C16 -10.2(4) . . . . ?
B1 O2 C17 C16 10.2(4) . . . . ?
B1 O2 C17 C18 -170.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bww17128
_database_code_depnum_ccdc_archive 'CCDC 1574741'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2017-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 B F2 N O2'
_chemical_formula_sum            'C18 H16 B F2 N O2'
_chemical_formula_weight         327.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.231(4)
_cell_length_b                   9.2009(18)
_cell_length_c                   16.416(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.76(3)
_cell_angle_gamma                90
_cell_volume                     3086.2(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.9934
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12172
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3095
_reflns_number_total             3513
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0839
_refine_ls_restrained_S_all      1.261
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+8.3736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1722
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.10267(10) 0.3928(2) 0.21405(13) 0.0492(6) Uani 1 1 d . . . . .
F2 F 0.17665(9) 0.2112(2) 0.23136(11) 0.0390(5) Uani 1 1 d . . . . .
O1 O 0.17959(11) 0.3658(3) 0.34386(13) 0.0394(6) Uani 1 1 d . . . . .
O2 O 0.09161(12) 0.1901(3) 0.29196(15) 0.0486(7) Uani 1 1 d . . . . .
N1 N 0.33411(11) 0.7097(3) 0.66351(14) 0.0257(5) Uani 1 1 d . . . . .
C1 C 0.43151(14) 0.8514(3) 0.64812(19) 0.0306(7) Uani 1 1 d . . . . .
H1 H 0.4427 0.8913 0.7036 0.037 Uiso 1 1 calc R . . . .
C2 C 0.46765(15) 0.8814(4) 0.5923(2) 0.0369(7) Uani 1 1 d . . . . .
H2 H 0.5048 0.9429 0.6100 0.044 Uiso 1 1 calc R . . . .
C3 C 0.45159(16) 0.8245(4) 0.5103(2) 0.0381(8) Uani 1 1 d . . . . .
H3 H 0.4778 0.8476 0.4735 0.046 Uiso 1 1 calc R . . . .
C4 C 0.39767(15) 0.7343(3) 0.48250(19) 0.0318(7) Uani 1 1 d . . . . .
H4 H 0.3864 0.6966 0.4265 0.038 Uiso 1 1 calc R . . . .
C5 C 0.36055(13) 0.7000(3) 0.53731(17) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.37788(13) 0.7600(3) 0.61971(17) 0.0254(6) Uani 1 1 d . . . . .
C7 C 0.30415(14) 0.6087(3) 0.53188(17) 0.0260(6) Uani 1 1 d . . . . .
C8 C 0.29036(13) 0.6162(3) 0.61200(17) 0.0252(6) Uani 1 1 d . . . . .
C9 C 0.23967(15) 0.5389(3) 0.62976(18) 0.0308(7) Uani 1 1 d . . . . .
H9 H 0.2314 0.5441 0.6837 0.037 Uiso 1 1 calc R . . . .
C10 C 0.20185(15) 0.4542(3) 0.56596(18) 0.0309(7) Uani 1 1 d . . . . .
H10 H 0.1669 0.3999 0.5768 0.037 Uiso 1 1 calc R . . . .
C11 C 0.21285(13) 0.4447(3) 0.48495(17) 0.0255(6) Uani 1 1 d . . . . .
C12 C 0.26440(13) 0.5239(3) 0.46828(17) 0.0263(6) Uani 1 1 d . . . . .
H12 H 0.2721 0.5196 0.4140 0.032 Uiso 1 1 calc R . . . .
C13 C 0.17040(14) 0.3579(3) 0.41870(17) 0.0271(6) Uani 1 1 d . . . . .
C14 C 0.12174(15) 0.2674(3) 0.43159(19) 0.0355(7) Uani 1 1 d . . . . .
H14 H 0.1144 0.2635 0.4861 0.043 Uiso 1 1 calc R . . . .
C15 C 0.08399(14) 0.1834(3) 0.36779(19) 0.0301(6) Uani 1 1 d . . . . .
C16 C 0.03191(15) 0.0826(4) 0.3783(2) 0.0381(8) Uani 1 1 d . . . . .
H16A H -0.0110 0.1192 0.3461 0.057 Uiso 1 1 calc GR . . . .
H16B H 0.0333 0.0763 0.4383 0.057 Uiso 1 1 calc GR . . . .
H16C H 0.0391 -0.0140 0.3574 0.057 Uiso 1 1 calc GR . . . .
C17 C 0.33708(15) 0.7454(3) 0.75141(18) 0.0311(7) Uani 1 1 d . . . . .
H17A H 0.2926 0.7385 0.7595 0.037 Uiso 1 1 calc R . . . .
H17B H 0.3525 0.8467 0.7634 0.037 Uiso 1 1 calc R . . . .
C18 C 0.38265(18) 0.6441(4) 0.8129(2) 0.0422(8) Uani 1 1 d . . . . .
H18A H 0.3665 0.5441 0.8028 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.3843 0.6723 0.8710 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.4266 0.6503 0.8048 0.063 Uiso 1 1 calc GR . . . .
B1 B 0.13747(18) 0.2901(4) 0.2688(2) 0.0361(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
F1 B1 1.373(5) . ?
F2 B1 1.369(4) . ?
O1 C13 1.297(3) . ?
O1 B1 1.485(4) . ?
O2 C15 1.300(4) . ?
O2 B1 1.463(4) . ?
N1 C6 1.399(4) . ?
N1 C8 1.375(4) . ?
N1 C17 1.464(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(4) . ?
C1 C6 1.390(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 C6 1.414(4) . ?
C5 C7 1.446(4) . ?
C7 C8 1.425(4) . ?
C7 C12 1.390(4) . ?
C8 C9 1.386(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.414(4) . ?
C11 C12 1.402(4) . ?
C11 C13 1.450(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(4) . ?
C15 C16 1.489(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.515(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 B1 123.2(3) . . ?
C15 O2 B1 122.9(3) . . ?
C6 N1 C17 125.1(2) . . ?
C8 N1 C6 108.8(2) . . ?
C8 N1 C17 126.0(2) . . ?
C2 C1 H1 121.5 . . ?
C2 C1 C6 116.9(3) . . ?
C6 C1 H1 121.5 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 C7 134.5(3) . . ?
C6 C5 C7 106.4(2) . . ?
N1 C6 C5 109.0(2) . . ?
C1 C6 N1 128.7(3) . . ?
C1 C6 C5 122.3(3) . . ?
C8 C7 C5 106.8(2) . . ?
C12 C7 C5 134.1(3) . . ?
C12 C7 C8 119.0(3) . . ?
N1 C8 C7 108.9(2) . . ?
N1 C8 C9 128.7(3) . . ?
C9 C8 C7 122.4(3) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 C8 117.2(3) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.7(3) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C13 120.8(3) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 C13 120.0(3) . . ?
C7 C12 C11 119.5(3) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O1 C13 C11 117.2(3) . . ?
O1 C13 C14 119.2(3) . . ?
C14 C13 C11 123.6(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 H14 119.1 . . ?
O2 C15 C14 120.4(3) . . ?
O2 C15 C16 115.4(3) . . ?
C14 C15 C16 124.1(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
N1 C17 C18 111.6(3) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 B1 O1 108.4(3) . . ?
F1 B1 O2 109.0(3) . . ?
F2 B1 F1 110.8(3) . . ?
F2 B1 O1 108.6(3) . . ?
F2 B1 O2 108.2(3) . . ?
O2 B1 O1 111.9(3) . . ?

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
O1 C13 C14 C15 1.5(5) . . . . ?
N1 C8 C9 C10 178.7(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C1 C6 N1 178.5(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C7 -177.6(3) . . . . ?
C4 C5 C6 N1 -179.6(3) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C7 C8 178.2(3) . . . . ?
C4 C5 C7 C12 -2.5(6) . . . . ?
C5 C7 C8 N1 1.7(3) . . . . ?
C5 C7 C8 C9 -178.8(3) . . . . ?
C5 C7 C12 C11 179.0(3) . . . . ?
C6 N1 C8 C7 -2.0(3) . . . . ?
C6 N1 C8 C9 178.5(3) . . . . ?
C6 N1 C17 C18 -85.6(4) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C6 C5 C7 C8 -0.7(3) . . . . ?
C6 C5 C7 C12 178.7(3) . . . . ?
C7 C5 C6 N1 -0.5(3) . . . . ?
C7 C5 C6 C1 178.4(3) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 N1 C6 C1 -177.2(3) . . . . ?
C8 N1 C6 C5 1.5(3) . . . . ?
C8 N1 C17 C18 90.9(3) . . . . ?
C8 C7 C12 C11 -1.7(4) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 C13 -177.9(3) . . . . ?
C10 C11 C12 C7 0.8(4) . . . . ?
C10 C11 C13 O1 173.4(3) . . . . ?
C10 C11 C13 C14 -7.2(4) . . . . ?
C11 C13 C14 C15 -177.9(3) . . . . ?
C12 C7 C8 N1 -177.8(2) . . . . ?
C12 C7 C8 C9 1.8(4) . . . . ?
C12 C11 C13 O1 -4.8(4) . . . . ?
C12 C11 C13 C14 174.6(3) . . . . ?
C13 O1 B1 F1 111.7(3) . . . . ?
C13 O1 B1 F2 -127.9(3) . . . . ?
C13 O1 B1 O2 -8.5(5) . . . . ?
C13 C11 C12 C7 179.0(3) . . . . ?
C13 C14 C15 O2 -2.2(5) . . . . ?
C13 C14 C15 C16 178.9(3) . . . . ?
C15 O2 B1 F1 -112.0(3) . . . . ?
C15 O2 B1 F2 127.4(3) . . . . ?
C15 O2 B1 O1 7.9(5) . . . . ?
C17 N1 C6 C1 -0.2(5) . . . . ?
C17 N1 C6 C5 178.5(3) . . . . ?
C17 N1 C8 C7 -178.9(3) . . . . ?
C17 N1 C8 C9 1.5(5) . . . . ?
B1 O1 C13 C11 -176.3(3) . . . . ?
B1 O1 C13 C14 4.3(5) . . . . ?
B1 O2 C15 C14 -3.1(5) . . . . ?
B1 O2 C15 C16 175.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1574742'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2017-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H19 B2 F4 N O4'
_chemical_formula_sum            'C22 H19 B2 F4 N O4'
_chemical_formula_weight         459.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x+1/2, z+1/2'
3 '-x+1/2, -y+1/2, z'
4 'y+1/2, -x, z+1/2'
5 '-x, -y, -z'
6 'y, -x-1/2, -z-1/2'
7 'x-1/2, y-1/2, -z'
8 '-y-1/2, x, -z-1/2'

_cell_length_a                   23.179(3)
_cell_length_b                   23.179(3)
_cell_length_c                   7.6814(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4127.0(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12141
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.2424
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7766
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26668
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3526
_reflns_number_total             3596
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.392
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0910
_refine_ls_restrained_S_all      1.392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0054P)²+7.3875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1425
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C22(H22), C38(H38), C39(H39), C40(H40), C47(H47), C48(H48), C61(H61)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C58(H58A,H58B,H58C), C63(H63A,H63B,H63C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F2 F 0.04706(11) 0.33269(9) 0.1027(3) 0.0465(7) Uani 1 d . . .
F6 F 0.12020(11) 0.27885(11) -0.0081(3) 0.0476(7) Uani 1 d . . .
F20 F 0.11767(11) -0.29439(10) 0.4725(4) 0.0500(7) Uani 1 d . . .
F32 F 0.08491(13) -0.26387(13) 0.7331(4) 0.0651(9) Uani 1 d . . .
O1 O 0.04389(11) 0.23328(10) 0.1320(3) 0.0299(6) Uani 1 d . . .
O9 O 0.11353(12) 0.29203(11) 0.2922(4) 0.0372(7) Uani 1 d . . .
O10 O 0.16805(13) -0.22356(11) 0.6180(4) 0.0454(8) Uani 1 d . . .
O25 O 0.07237(12) -0.20510(10) 0.4929(4) 0.0357(7) Uani 1 d . . .
N14 N -0.07515(12) -0.00984(12) 0.1379(4) 0.0255(7) Uani 1 d . . .
C12 C 0.04526(15) -0.11648(14) 0.3727(5) 0.0232(8) Uani 1 d . . .
C17 C -0.04909(16) -0.11054(15) 0.2322(5) 0.0274(8) Uani 1 d . . .
H17 H -0.0834 -0.1284 0.1908 0.033 Uiso 1 calc . . R
C21 C -0.04878(15) 0.04358(15) 0.1525(5) 0.0242(8) Uani 1 d . . .
C22 C -0.03250(15) 0.14348(15) 0.1195(5) 0.0253(8) Uani 1 d . . .
H22 H -0.0440 0.1802 0.0772 0.030 Uiso 1 calc . . R
C24 C -0.03992(15) -0.05098(15) 0.2149(5) 0.0233(8) Uani 1 d . . .
C28 C 0.02088(15) 0.13833(15) 0.2081(5) 0.0248(8) Uani 1 d . . .
C29 C 0.08885(16) -0.15275(15) 0.4561(5) 0.0257(8) Uani 1 d . . .
C34 C 0.00474(14) 0.03706(14) 0.2404(4) 0.0210(7) Uani 1 d . . .
C37 C 0.16495(18) 0.25791(18) 0.5370(6) 0.0434(11) Uani 1 d . . .
H37A H 0.1948 0.2854 0.5013 0.065 Uiso 1 calc . . GR
H37B H 0.1831 0.2216 0.5730 0.065 Uiso 1 calc . . GR
H37C H 0.1430 0.2740 0.6347 0.065 Uiso 1 calc . . GR
C38 C -0.06790(15) 0.09703(15) 0.0930(5) 0.0251(8) Uani 1 d . . .
H38 H -0.1041 0.1011 0.0362 0.030 Uiso 1 calc . . R
C39 C 0.03920(15) 0.08468(15) 0.2699(5) 0.0241(8) Uani 1 d . . .
H39 H 0.0747 0.0810 0.3309 0.029 Uiso 1 calc . . R
C40 C -0.00611(16) -0.14186(16) 0.3118(5) 0.0282(8) Uani 1 d . . .
H40 H -0.0113 -0.1822 0.3262 0.034 Uiso 1 calc . . R
C45 C 0.01057(15) -0.02425(14) 0.2791(5) 0.0229(8) Uani 1 d . . .
C47 C 0.10010(15) 0.19427(15) 0.3571(5) 0.0263(8) Uani 1 d . . .
H47 H 0.1123 0.1612 0.4205 0.032 Uiso 1 calc . . R
C48 C 0.05311(15) -0.05672(15) 0.3572(5) 0.0242(8) Uani 1 d . . .
H48 H 0.0872 -0.0389 0.3997 0.029 Uiso 1 calc . . R
C52 C 0.05652(15) 0.18933(15) 0.2320(5) 0.0242(8) Uani 1 d . . .
C53 C -0.12982(15) -0.02062(16) 0.0482(5) 0.0283(8) Uani 1 d . . .
H53A H -0.1292 -0.0600 -0.0016 0.034 Uiso 1 calc . . R
H53B H -0.1338 0.0070 -0.0492 0.034 Uiso 1 calc . . R
C54 C 0.12527(16) 0.24681(16) 0.3880(5) 0.0309(9) Uani 1 d . . .
C57 C 0.18328(17) -0.17160(16) 0.5704(5) 0.0320(9) Uani 1 d . . .
C58 C -0.18127(16) -0.01491(19) 0.1670(6) 0.0405(10) Uani 1 d . . .
H58A H -0.2168 -0.0204 0.0997 0.061 Uiso 1 calc . . GR
H58B H -0.1815 0.0236 0.2197 0.061 Uiso 1 calc . . GR
H58C H -0.1791 -0.0442 0.2588 0.061 Uiso 1 calc . . GR
C61 C 0.14466(16) -0.13489(17) 0.4919(5) 0.0321(9) Uani 1 d . . .
H61 H 0.1563 -0.0969 0.4619 0.039 Uiso 1 calc . . R
C63 C 0.24484(17) -0.15671(18) 0.6012(6) 0.0417(11) Uani 1 d . . .
H63A H 0.2583 -0.1758 0.7076 0.063 Uiso 1 calc . . GR
H63B H 0.2487 -0.1148 0.6140 0.063 Uiso 1 calc . . GR
H63C H 0.2681 -0.1697 0.5021 0.063 Uiso 1 calc . . GR
B41 B 0.0813(2) 0.28508(19) 0.1262(7) 0.0355(11) Uani 1 d . . .
B46 B 0.1105(2) -0.24782(19) 0.5809(7) 0.0382(11) Uani 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 B41 1.371(5) . ?
F6 B41 1.378(5) . ?
F20 B46 1.373(5) . ?
F32 B46 1.362(6) . ?
O1 C52 1.309(4) . ?
O1 B41 1.481(5) . ?
O9 C54 1.309(5) . ?
O9 B41 1.487(6) . ?
O10 C57 1.307(5) . ?
O10 B46 1.475(6) . ?
O25 C29 1.303(4) . ?
O25 B46 1.489(5) . ?
N14 C21 1.385(4) . ?
N14 C24 1.388(4) . ?
N14 C53 1.464(4) . ?
C12 C29 1.462(5) . ?
C12 C40 1.408(5) . ?
C12 C48 1.402(5) . ?
C17 H17 0.9500 . ?
C17 C24 1.403(5) . ?
C17 C40 1.376(5) . ?
C21 C34 1.421(5) . ?
C21 C38 1.393(5) . ?
C22 H22 0.9500 . ?
C22 C28 1.417(5) . ?
C22 C38 1.369(5) . ?
C24 C45 1.413(5) . ?
C28 C39 1.397(5) . ?
C28 C52 1.454(5) . ?
C29 C61 1.386(5) . ?
C34 C39 1.381(5) . ?
C34 C45 1.458(5) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37 C54 1.491(6) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C45 C48 1.378(5) . ?
C47 H47 0.9500 . ?
C47 C52 1.399(5) . ?
C47 C54 1.371(5) . ?
C48 H48 0.9500 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C53 C58 1.507(5) . ?
C57 C61 1.374(5) . ?
C57 C63 1.487(5) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C61 H61 0.9500 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C52 O1 B41 121.2(3) . . ?
C54 O9 B41 120.0(3) . . ?
C57 O10 B46 122.8(3) . . ?
C29 O25 B46 122.9(3) . . ?
C21 N14 C24 108.7(3) . . ?
C21 N14 C53 124.9(3) . . ?
C24 N14 C53 126.4(3) . . ?
C40 C12 C29 119.3(3) . . ?
C48 C12 C29 121.1(3) . . ?
C48 C12 C40 119.6(3) . . ?
C24 C17 H17 121.6 . . ?
C40 C17 H17 121.6 . . ?
C40 C17 C24 116.8(3) . . ?
N14 C21 C34 109.2(3) . . ?
N14 C21 C38 128.9(3) . . ?
C38 C21 C34 121.9(3) . . ?
C28 C22 H22 119.1 . . ?
C38 C22 H22 119.1 . . ?
C38 C22 C28 121.9(3) . . ?
N14 C24 C17 128.8(3) . . ?
N14 C24 C45 109.6(3) . . ?
C17 C24 C45 121.6(3) . . ?
C22 C28 C52 119.2(3) . . ?
C39 C28 C22 120.2(3) . . ?
C39 C28 C52 120.5(3) . . ?
O25 C29 C12 115.3(3) . . ?
O25 C29 C61 120.6(3) . . ?
C61 C29 C12 124.1(3) . . ?
C21 C34 C45 106.3(3) . . ?
C39 C34 C21 119.9(3) . . ?
C39 C34 C45 133.8(3) . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C54 C37 H37A 109.5 . . ?
C54 C37 H37B 109.5 . . ?
C54 C37 H37C 109.5 . . ?
C21 C38 H38 121.3 . . ?
C22 C38 C21 117.4(3) . . ?
C22 C38 H38 121.3 . . ?
C28 C39 H39 120.7 . . ?
C34 C39 C28 118.7(3) . . ?
C34 C39 H39 120.7 . . ?
C12 C40 H40 118.7 . . ?
C17 C40 C12 122.7(3) . . ?
C17 C40 H40 118.7 . . ?
C24 C45 C34 106.2(3) . . ?
C48 C45 C24 120.3(3) . . ?
C48 C45 C34 133.4(3) . . ?
C52 C47 H47 120.0 . . ?
C54 C47 H47 120.0 . . ?
C54 C47 C52 119.9(3) . . ?
C12 C48 H48 120.5 . . ?
C45 C48 C12 118.9(3) . . ?
C45 C48 H48 120.5 . . ?
O1 C52 C28 115.6(3) . . ?
O1 C52 C47 120.1(3) . . ?
C47 C52 C28 124.3(3) . . ?
N14 C53 H53A 109.1 . . ?
N14 C53 H53B 109.1 . . ?
N14 C53 C58 112.7(3) . . ?
H53A C53 H53B 107.8 . . ?
C58 C53 H53A 109.1 . . ?
C58 C53 H53B 109.1 . . ?
O9 C54 C37 114.9(3) . . ?
O9 C54 C47 121.7(4) . . ?
C47 C54 C37 123.3(4) . . ?
O10 C57 C61 121.1(4) . . ?
O10 C57 C63 115.4(3) . . ?
C61 C57 C63 123.4(4) . . ?
C53 C58 H58A 109.5 . . ?
C53 C58 H58B 109.5 . . ?
C53 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C29 C61 H61 119.7 . . ?
C57 C61 C29 120.7(4) . . ?
C57 C61 H61 119.7 . . ?
C57 C63 H63A 109.5 . . ?
C57 C63 H63B 109.5 . . ?
C57 C63 H63C 109.5 . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
F2 B41 F6 111.4(4) . . ?
F2 B41 O1 108.6(4) . . ?
F2 B41 O9 108.4(3) . . ?
F6 B41 O1 108.7(3) . . ?
F6 B41 O9 108.9(4) . . ?
O1 B41 O9 110.8(3) . . ?
F20 B46 O10 107.9(4) . . ?
F20 B46 O25 108.6(4) . . ?
F32 B46 F20 111.0(4) . . ?
F32 B46 O10 109.4(4) . . ?
F32 B46 O25 108.2(4) . . ?
O10 B46 O25 111.8(3) . . ?

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
O10 C57 C61 C29 -2.0(6) . . . . ?
O25 C29 C61 C57 -1.5(6) . . . . ?
N14 C21 C34 C39 179.7(3) . . . . ?
N14 C21 C34 C45 0.4(4) . . . . ?
N14 C21 C38 C22 -178.0(4) . . . . ?
N14 C24 C45 C34 0.9(4) . . . . ?
N14 C24 C45 C48 -178.2(3) . . . . ?
C12 C29 C61 C57 -179.9(4) . . . . ?
C17 C24 C45 C34 -179.2(3) . . . . ?
C17 C24 C45 C48 1.6(5) . . . . ?
C21 N14 C24 C17 179.5(4) . . . . ?
C21 N14 C24 C45 -0.7(4) . . . . ?
C21 N14 C53 C58 -90.1(4) . . . . ?
C21 C34 C39 C28 -1.5(5) . . . . ?
C21 C34 C45 C24 -0.8(4) . . . . ?
C21 C34 C45 C48 178.1(4) . . . . ?
C22 C28 C39 C34 0.9(5) . . . . ?
C22 C28 C52 O1 -16.8(5) . . . . ?
C22 C28 C52 C47 160.2(3) . . . . ?
C24 N14 C21 C34 0.1(4) . . . . ?
C24 N14 C21 C38 179.4(4) . . . . ?
C24 N14 C53 C58 93.1(4) . . . . ?
C24 C17 C40 C12 -0.6(5) . . . . ?
C24 C45 C48 C12 -0.4(5) . . . . ?
C28 C22 C38 C21 -1.8(5) . . . . ?
C29 O25 B46 F20 -119.5(4) . . . . ?
C29 O25 B46 F32 120.0(4) . . . . ?
C29 O25 B46 O10 -0.6(6) . . . . ?
C29 C12 C40 C17 179.9(3) . . . . ?
C29 C12 C48 C45 -179.4(3) . . . . ?
C34 C21 C38 C22 1.2(5) . . . . ?
C34 C45 C48 C12 -179.2(4) . . . . ?
C38 C21 C34 C39 0.4(5) . . . . ?
C38 C21 C34 C45 -178.9(3) . . . . ?
C38 C22 C28 C39 0.7(5) . . . . ?
C38 C22 C28 C52 180.0(3) . . . . ?
C39 C28 C52 O1 162.4(3) . . . . ?
C39 C28 C52 C47 -20.5(5) . . . . ?
C39 C34 C45 C24 -180.0(4) . . . . ?
C39 C34 C45 C48 -1.1(7) . . . . ?
C40 C12 C29 O25 -10.7(5) . . . . ?
C40 C12 C29 C61 167.7(4) . . . . ?
C40 C12 C48 C45 -1.2(5) . . . . ?
C40 C17 C24 N14 178.6(3) . . . . ?
C40 C17 C24 C45 -1.1(5) . . . . ?
C45 C34 C39 C28 177.6(4) . . . . ?
C48 C12 C29 O25 167.4(3) . . . . ?
C48 C12 C29 C61 -14.1(6) . . . . ?
C48 C12 C40 C17 1.8(6) . . . . ?
C52 O1 B41 F2 -145.5(3) . . . . ?
C52 O1 B41 F6 93.2(4) . . . . ?
C52 O1 B41 O9 -26.5(5) . . . . ?
C52 C28 C39 C34 -178.3(3) . . . . ?
C52 C47 C54 O9 -6.5(6) . . . . ?
C52 C47 C54 C37 169.9(4) . . . . ?
C53 N14 C21 C34 -177.2(3) . . . . ?
C53 N14 C21 C38 2.1(6) . . . . ?
C53 N14 C24 C17 -3.2(6) . . . . ?
C53 N14 C24 C45 176.6(3) . . . . ?
C54 O9 B41 F2 145.9(3) . . . . ?
C54 O9 B41 F6 -92.7(4) . . . . ?
C54 O9 B41 O1 26.8(5) . . . . ?
C54 C47 C52 O1 7.1(5) . . . . ?
C54 C47 C52 C28 -169.8(3) . . . . ?
C57 O10 B46 F20 116.4(4) . . . . ?
C57 O10 B46 F32 -122.7(4) . . . . ?
C57 O10 B46 O25 -2.9(6) . . . . ?
C63 C57 C61 C29 175.5(4) . . . . ?
B41 O1 C52 C28 -172.0(3) . . . . ?
B41 O1 C52 C47 10.9(5) . . . . ?
B41 O9 C54 C37 171.4(4) . . . . ?
B41 O9 C54 C47 -11.9(5) . . . . ?
B46 O10 C57 C61 4.2(6) . . . . ?
B46 O10 C57 C63 -173.5(4) . . . . ?
B46 O25 C29 C12 -178.8(4) . . . . ?
B46 O25 C29 C61 2.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
