# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_S
_database_code_depnum_ccdc_archive 'CCDC 1998621'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2025-12-16 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;
_audit_creation_date             2025-12-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
gcampillo@reed.edu
?
?
?
?
?
_chemical_name_common            ?
_chemical_name_systematic        
"2,4-difluorophenylboronic acid catechol ester adduct of 4,4,'-azopyridine benzene solvate"
_chemical_formula_moiety         'C34 H22 B2 F4 N4 O4, C6 H6'
_chemical_formula_sum            'C40 H28 B2 F4 N4 O4'
_chemical_formula_weight         726.28
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5341(8)
_cell_length_b                   14.4259(14)
_cell_length_c                   16.8748(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.484(5)
_cell_angle_gamma                90
_cell_volume                     1832.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4171
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.0
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'reddish orange'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_av_unetI/netI     0.1185
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8676
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        23.999
_diffrn_reflns_theta_max         23.999
_diffrn_reflns_theta_min         2.824
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_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                1208
_reflns_number_total             2823
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1749
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      0.952
_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)+(0.1037P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.2100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C20, C22, H22, C23, C21, H23, C18, H21, C19, H18, H20, H19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C22(0.5) H22(0.5) C23(0.5) H23(0.5) C18(0.5) H18(0.5) C19(0.5)
 H19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C16(H16), C13(H13), C12(H12), C3(H3), C6(H6), C9(H9),
 C11(H11), C5(H5), C10(H10), C22(H22), C23(H23), C18(H18), C19(H19), C20(H20),
 C21(H21)
4.b Fitted hexagon refined as free rotating group:
 C22(C23,C18,C19,C20,C21)
;
_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
N2 N 0.4828(5) 0.0159(2) 0.03259(19) 0.0639(11) Uani 1 1 d . . . . .
F1 F 0.4878(5) -0.42543(17) 0.18448(17) 0.0881(10) Uani 1 1 d . . . . .
O1 O 0.3204(5) -0.21233(19) 0.34640(18) 0.0727(10) Uani 1 1 d . . . . .
O2 O 0.5722(5) -0.29143(18) 0.30599(16) 0.0666(10) Uani 1 1 d . . . . .
N1 N 0.4245(5) -0.1812(2) 0.21072(19) 0.0570(10) Uani 1 1 d . . . . .
C15 C 0.4678(6) -0.0547(3) 0.0921(3) 0.0569(12) Uani 1 1 d . . . . .
C14 C 0.5316(7) -0.1436(3) 0.0849(3) 0.0696(14) Uani 1 1 d . . . . .
H14 H 0.589577 -0.161737 0.039948 0.083 Uiso 1 1 calc R U . . .
C2 C 0.3091(7) -0.4128(3) 0.1982(3) 0.0656(13) Uani 1 1 d . . . . .
C17 C 0.3644(7) -0.0948(3) 0.2184(3) 0.0694(15) Uani 1 1 d . . . . .
H17 H 0.306715 -0.078197 0.263900 0.083 Uiso 1 1 calc R U . . .
C16 C 0.3867(7) -0.0296(3) 0.1597(3) 0.0723(15) Uani 1 1 d . . . . .
H16 H 0.346881 0.030800 0.166089 0.087 Uiso 1 1 calc R U . . .
C1 C 0.2620(8) -0.3364(3) 0.2409(2) 0.0598(13) Uani 1 1 d . . . . .
C13 C 0.5079(7) -0.2037(3) 0.1448(3) 0.0726(15) Uani 1 1 d . . . . .
H13 H 0.551689 -0.263661 0.140186 0.087 Uiso 1 1 calc R U . . .
C12 C 0.4689(11) -0.1370(3) 0.4622(3) 0.0916(19) Uani 1 1 d . . . . .
H12 H 0.368232 -0.106295 0.478543 0.110 Uiso 1 1 calc R U . . .
B14 B 0.3933(8) -0.2615(3) 0.2796(3) 0.0612(15) Uani 1 1 d . . . . .
C7 C 0.4623(9) -0.1931(3) 0.3959(3) 0.0724(16) Uani 1 1 d . . . . .
C8 C 0.6123(9) -0.2395(3) 0.3728(3) 0.0678(14) Uani 1 1 d . . . . .
C3 C 0.1993(9) -0.4764(4) 0.1630(3) 0.0825(16) Uani 1 1 d . . . . .
H3 H 0.242205 -0.526967 0.135495 0.099 Uiso 1 1 calc R U . . .
F2 F -0.0976(5) -0.5218(3) 0.1368(2) 0.1400(15) Uani 1 1 d . . . . .
C6 C 0.0818(9) -0.3267(4) 0.2452(3) 0.0850(17) Uani 1 1 d . . . . .
H6 H 0.039564 -0.276248 0.273102 0.102 Uiso 1 1 calc R U . . .
C9 C 0.7704(9) -0.2327(3) 0.4132(3) 0.0841(17) Uani 1 1 d . . . . .
H9 H 0.869991 -0.264754 0.397448 0.101 Uiso 1 1 calc R U . . .
C11 C 0.6298(13) -0.1281(4) 0.5031(3) 0.102(2) Uani 1 1 d . . . . .
H11 H 0.638172 -0.089417 0.547247 0.122 Uiso 1 1 calc R U . . .
C5 C -0.0420(9) -0.3876(5) 0.2104(4) 0.0984(19) Uani 1 1 d . . . . .
H5 H -0.163393 -0.378248 0.214349 0.118 Uiso 1 1 calc R U . . .
C10 C 0.7773(11) -0.1744(4) 0.4809(3) 0.098(2) Uani 1 1 d . . . . .
H10 H 0.883639 -0.167614 0.510436 0.118 Uiso 1 1 calc R U . . .
C4 C 0.0226(11) -0.4617(5) 0.1702(3) 0.0914(19) Uani 1 1 d . . . . .
C22 C -0.064(2) 0.0197(13) 0.0758(12) 0.235(13) Uani 0.5 1 d G . P A -1
H22 H -0.118751 0.064355 0.106253 0.282 Uiso 0.5 1 calc R U P A -1
C23 C -0.038(2) -0.0693(17) 0.1055(8) 0.232(13) Uani 0.5 1 d G . P A -1
H23 H -0.074390 -0.084219 0.155873 0.278 Uiso 0.5 1 calc R U P A -1
C18 C 0.043(2) -0.1360(10) 0.0599(14) 0.212(9) Uani 0.5 1 d G . P A -1
H18 H 0.061117 -0.195568 0.079838 0.254 Uiso 0.5 1 calc R U P A -1
C19 C 0.098(2) -0.1137(14) -0.0153(13) 0.199(12) Uani 0.5 1 d G . P A -1
H19 H 0.152264 -0.158344 -0.045818 0.239 Uiso 0.5 1 calc R U P A -1
C20 C 0.071(3) -0.0247(18) -0.0451(10) 0.202(12) Uani 0.5 1 d G . P A -1
H20 H 0.107905 -0.009771 -0.095440 0.242 Uiso 0.5 1 calc R U P A -1
C21 C -0.010(4) 0.0420(11) 0.0005(14) 0.214(11) Uani 0.5 1 d G . P A -1
H21 H -0.027602 0.101579 -0.019406 0.257 Uiso 0.5 1 calc R U P A -1


_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
N2 N2 1.230(6) 3_655 ?
N2 C15 1.438(5) . ?
F1 C2 1.388(5) . ?
O1 B14 1.459(6) . ?
O1 C7 1.357(6) . ?
O2 B14 1.466(6) . ?
O2 C8 1.376(5) . ?
N1 C17 1.335(5) . ?
N1 C13 1.341(5) . ?
N1 B14 1.664(6) . ?
C15 C14 1.376(6) . ?
C15 C16 1.365(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.350(6) . ?
C2 C1 1.371(6) . ?
C2 C3 1.355(7) . ?
C17 H17 0.9300 . ?
C17 C16 1.382(6) . ?
C16 H16 0.9300 . ?
C1 B14 1.588(7) . ?
C1 C6 1.370(7) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C12 C7 1.379(7) . ?
C12 C11 1.375(9) . ?
C7 C8 1.384(7) . ?
C8 C9 1.350(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(8) . ?
F2 C4 1.358(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.393(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.417(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.363(9) . ?
C5 H5 0.9300 . ?
C5 C4 1.366(8) . ?
C10 H10 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.3900 . ?
C22 C21 1.3900 . ?
C23 H23 0.9300 . ?
C23 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C21 1.3900 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N2 C15 112.7(4) 3_655 . ?
C7 O1 B14 105.2(4) . . ?
C8 O2 B14 104.7(4) . . ?
C17 N1 C13 118.7(4) . . ?
C17 N1 B14 121.6(3) . . ?
C13 N1 B14 119.8(3) . . ?
C14 C15 N2 124.1(4) . . ?
C16 C15 N2 116.6(4) . . ?
C16 C15 C14 119.4(4) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C1 C2 F1 117.9(5) . . ?
C3 C2 F1 114.6(5) . . ?
C3 C2 C1 127.4(6) . . ?
N1 C17 H17 119.5 . . ?
N1 C17 C16 120.9(4) . . ?
C16 C17 H17 119.5 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C2 C1 B14 126.4(5) . . ?
C6 C1 C2 113.0(5) . . ?
C6 C1 B14 120.6(5) . . ?
N1 C13 C14 123.2(4) . . ?
N1 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C7 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C11 C12 C7 117.5(6) . . ?
O1 B14 O2 106.3(4) . . ?
O1 B14 N1 105.7(3) . . ?
O1 B14 C1 113.6(5) . . ?
O2 B14 N1 105.2(4) . . ?
O2 B14 C1 118.2(4) . . ?
C1 B14 N1 106.9(4) . . ?
O1 C7 C12 128.2(6) . . ?
O1 C7 C8 111.0(4) . . ?
C12 C7 C8 120.8(6) . . ?
O2 C8 C7 110.0(5) . . ?
C9 C8 O2 127.7(5) . . ?
C9 C8 C7 122.4(5) . . ?
C2 C3 H3 122.1 . . ?
C2 C3 C4 115.9(6) . . ?
C4 C3 H3 122.1 . . ?
C1 C6 H6 118.0 . . ?
C1 C6 C5 124.0(6) . . ?
C5 C6 H6 118.0 . . ?
C8 C9 H9 121.6 . . ?
C8 C9 C10 116.8(6) . . ?
C10 C9 H9 121.6 . . ?
C12 C11 H11 119.1 . . ?
C10 C11 C12 121.8(6) . . ?
C10 C11 H11 119.1 . . ?
C6 C5 H5 121.4 . . ?
C4 C5 C6 117.2(6) . . ?
C4 C5 H5 121.4 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.6 . . ?
C3 C4 C5 122.6(6) . . ?
F2 C4 C3 120.0(7) . . ?
F2 C4 C5 117.4(7) . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C18 C23 H23 120.0 . . ?
C23 C18 H18 120.0 . . ?
C19 C18 C23 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?

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
N2 N2 C15 C14 17.1(7) 3_655 . . . ?
N2 N2 C15 C16 -163.8(5) 3_655 . . . ?
N2 C15 C14 C13 -179.5(5) . . . . ?
N2 C15 C16 C17 178.5(4) . . . . ?
F1 C2 C1 B14 -2.5(6) . . . . ?
F1 C2 C1 C6 174.9(4) . . . . ?
F1 C2 C3 C4 -175.1(4) . . . . ?
O1 C7 C8 O2 0.0(5) . . . . ?
O1 C7 C8 C9 -179.1(4) . . . . ?
O2 C8 C9 C10 -179.7(4) . . . . ?
N1 C17 C16 C15 1.5(8) . . . . ?
C15 C14 C13 N1 0.4(8) . . . . ?
C14 C15 C16 C17 -2.3(8) . . . . ?
C2 C1 B14 O1 -155.8(4) . . . . ?
C2 C1 B14 O2 -30.2(6) . . . . ?
C2 C1 B14 N1 88.0(5) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C2 C3 C4 F2 -180.0(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C17 N1 C13 C14 -1.3(8) . . . . ?
C17 N1 B14 O1 -8.5(6) . . . . ?
C17 N1 B14 O2 -120.7(4) . . . . ?
C17 N1 B14 C1 112.8(5) . . . . ?
C16 C15 C14 C13 1.4(7) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C1 C6 C5 C4 0.5(8) . . . . ?
C13 N1 C17 C16 0.3(7) . . . . ?
C13 N1 B14 O1 173.2(4) . . . . ?
C13 N1 B14 O2 60.9(5) . . . . ?
C13 N1 B14 C1 -65.5(6) . . . . ?
C12 C7 C8 O2 179.4(4) . . . . ?
C12 C7 C8 C9 0.2(7) . . . . ?
C12 C11 C10 C9 1.1(8) . . . . ?
B14 O1 C7 C12 170.5(4) . . . . ?
B14 O1 C7 C8 -10.3(5) . . . . ?
B14 O2 C8 C7 10.2(4) . . . . ?
B14 O2 C8 C9 -170.8(5) . . . . ?
B14 N1 C17 C16 -178.1(5) . . . . ?
B14 N1 C13 C14 177.2(4) . . . . ?
B14 C1 C6 C5 177.7(5) . . . . ?
C7 O1 B14 O2 16.2(4) . . . . ?
C7 O1 B14 N1 -95.3(4) . . . . ?
C7 O1 B14 C1 147.8(4) . . . . ?
C7 C12 C11 C10 -1.6(8) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C8 O2 B14 O1 -16.1(4) . . . . ?
C8 O2 B14 N1 95.8(3) . . . . ?
C8 O2 B14 C1 -145.1(4) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C3 C2 C1 B14 -178.2(5) . . . . ?
C3 C2 C1 C6 -0.9(7) . . . . ?
C6 C1 B14 O1 27.0(6) . . . . ?
C6 C1 B14 O2 152.6(4) . . . . ?
C6 C1 B14 N1 -89.2(5) . . . . ?
C6 C5 C4 C3 -0.6(9) . . . . ?
C6 C5 C4 F2 179.4(5) . . . . ?
C11 C12 C7 O1 -179.9(5) . . . . ?
C11 C12 C7 C8 0.9(7) . . . . ?
C22 C23 C18 C19 0.0 . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C21 C22 C23 C18 0.0 . . . . ?

_olex2_submission_original_sample_id S-298K
_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_D
_database_code_depnum_ccdc_archive 'CCDC 1998622'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2025-12-16 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;
_audit_creation_date             2025-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
gcampillo@reed.edu
?
?
?
?
?
_chemical_name_common            ?
_chemical_name_systematic        
"2,4-difluorophenylboronic acid catechol ester adduct of 4,4,'-azopyridine"
_chemical_formula_moiety         'C34 H22 B2 F4 N4 O4'
_chemical_formula_sum            'C34 H22 B2 F4 N4 O4'
_chemical_formula_weight         648.17
_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'

_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                   7.3611(12)
_cell_length_b                   13.623(2)
_cell_length_c                   15.855(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.723(11)
_cell_angle_gamma                90
_cell_volume                     1550.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4171
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'reddish orange'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8293
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.498
_diffrn_reflns_theta_max         24.498
_diffrn_reflns_theta_min         2.634
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_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                1059
_reflns_number_total             2587
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2115
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      0.999
_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)+(0.0715P)²+0.3751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(N2B) = Uanis(N2A)
2. Others
 Sof(N2A)=1-FVAR(1)
 Sof(N2B)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C17(H17), C13(H13), C16(H16), C12(H12), C14(H14),
 C9(H9), C11(H11), C10(H10)
3.b Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2)
;
_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 0.8246(3) 0.56191(19) 0.82531(17) 0.0976(9) Uani 1 1 d . . . . .
O1 O 0.8304(4) 0.6838(2) 0.66216(18) 0.0738(9) Uani 1 1 d . . . . .
O2 O 0.5599(4) 0.7802(2) 0.6386(2) 0.0793(9) Uani 1 1 d . . . . .
N1 N 0.7748(6) 0.7899(3) 0.7832(2) 0.0722(10) Uani 1 1 d . . . . .
F2 F 0.2480(4) 0.4123(2) 0.8124(2) 0.1309(12) Uani 1 1 d . . . . .
C1 C 0.5589(5) 0.6326(2) 0.73637(19) 0.0641(12) Uani 1 1 d G . . . .
C6 C 0.3673(5) 0.6305(2) 0.70445(18) 0.0838(14) Uani 1 1 d G . . . .
H6 H 0.310271 0.678393 0.665738 0.101 Uiso 1 1 calc R U . . .
C5 C 0.2609(3) 0.5568(3) 0.7304(2) 0.0953(16) Uani 1 1 d G . . . .
H5 H 0.132658 0.555417 0.709028 0.114 Uiso 1 1 calc R U . . .
C4 C 0.3461(5) 0.4853(2) 0.7882(2) 0.0901(15) Uani 1 1 d G . . . .
C3 C 0.5377(5) 0.4874(2) 0.82016(18) 0.0795(13) Uani 1 1 d G . . . .
H3 H 0.594688 0.439478 0.858874 0.095 Uiso 1 1 calc R U . . .
C2 C 0.6441(3) 0.5610(3) 0.79423(19) 0.0694(12) Uani 1 1 d G . . . .
C7 C 0.6580(8) 0.7995(4) 0.5774(3) 0.0767(13) Uani 1 1 d . . . . .
C8 C 0.8187(8) 0.7438(4) 0.5905(3) 0.0780(14) Uani 1 1 d . . . . .
C17 C 0.9541(8) 0.7868(4) 0.8198(3) 0.0897(15) Uani 1 1 d . . . . .
H17 H 1.028830 0.740975 0.800236 0.108 Uiso 1 1 calc R U . . .
C13 C 0.6682(8) 0.8556(4) 0.8117(3) 0.0960(16) Uani 1 1 d . . . . .
H13 H 0.541612 0.858175 0.786604 0.115 Uiso 1 1 calc R U . . .
C16 C 1.0343(9) 0.8492(5) 0.8859(4) 0.1064(19) Uani 1 1 d . . . . .
H16 H 1.161299 0.845011 0.909910 0.128 Uiso 1 1 calc R U . . .
C12 C 0.6154(8) 0.8646(4) 0.5107(4) 0.0961(16) Uani 1 1 d . . . . .
H12 H 0.506865 0.901814 0.501060 0.115 Uiso 1 1 calc R U . . .
C14 C 0.7423(10) 0.9200(4) 0.8778(4) 0.1108(19) Uani 1 1 d . . . . .
H14 H 0.665765 0.965766 0.896344 0.133 Uiso 1 1 calc R U . . .
B1 B 0.6764(8) 0.7156(4) 0.7012(3) 0.0710(15) Uani 1 1 d . . . . .
C9 C 0.9449(8) 0.7505(4) 0.5392(4) 0.1018(17) Uani 1 1 d . . . . .
H9 H 1.052555 0.712666 0.548510 0.122 Uiso 1 1 calc R U . . .
C11 C 0.7394(11) 0.8726(5) 0.4589(4) 0.121(2) Uani 1 1 d . . . . .
H11 H 0.713266 0.916581 0.412946 0.146 Uiso 1 1 calc R U . . .
C10 C 0.8997(11) 0.8196(6) 0.4707(4) 0.125(2) Uani 1 1 d . . . . .
H10 H 0.980225 0.828725 0.433724 0.150 Uiso 1 1 calc R U . . .
C15 C 0.9291(11) 0.9165(5) 0.9161(4) 0.108(2) Uani 1 1 d . . . . .
N2B N 0.9520(16) 1.0228(8) 1.0185(8) 0.082(3) Uani 0.68(2) 1 d . . P A 1
N2A N 0.906(4) 0.9954(19) 0.9852(16) 0.082(3) Uani 0.32(2) 1 d . . P A 2


_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 C2 1.312(3) . ?
O1 C8 1.386(5) . ?
O1 B1 1.472(6) . ?
B1 N1 1.681(6) . yes
O2 C7 1.356(5) . ?
O2 B1 1.457(5) . ?
N1 C17 1.320(5) . ?
N1 C13 1.333(5) . ?
N1 B1 1.681(6) . ?
F2 C4 1.334(4) . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C1 B1 1.596(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C7 C8 1.382(6) . ?
C7 C12 1.364(6) . ?
C8 C9 1.365(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.377(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.354(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.360(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.420(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.360(8) . ?
C10 H10 0.9300 . ?
C15 N2B 1.458(17) 3_777 ?
C15 N2A 1.57(3) . ?
N2B N2B 1.19(2) 3_777 ?
N2A N2A 1.36(5) 3_777 ?

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
C8 O1 B1 104.9(4) . . ?
C7 O2 B1 106.2(4) . . ?
C17 N1 C13 118.5(4) . . ?
C17 N1 B1 122.7(4) . . ?
C13 N1 B1 118.7(4) . . ?
C6 C1 C2 120.0 . . ?
C6 C1 B1 118.2(3) . . ?
C2 C1 B1 121.8(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
F2 C4 C5 121.2(3) . . ?
F2 C4 C3 118.7(3) . . ?
C3 C4 C5 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
F1 C2 C1 120.9(3) . . ?
F1 C2 C3 119.1(3) . . ?
C3 C2 C1 120.0 . . ?
O2 C7 C8 111.0(5) . . ?
O2 C7 C12 127.8(6) . . ?
C12 C7 C8 121.1(5) . . ?
C7 C8 O1 110.1(5) . . ?
C9 C8 O1 126.9(5) . . ?
C9 C8 C7 123.1(5) . . ?
N1 C17 H17 118.8 . . ?
N1 C17 C16 122.4(5) . . ?
C16 C17 H17 118.8 . . ?
N1 C13 H13 119.3 . . ?
N1 C13 C14 121.3(5) . . ?
C14 C13 H13 119.3 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16 119.9 . . ?
C7 C12 H12 121.6 . . ?
C11 C12 C7 116.8(6) . . ?
C11 C12 H12 121.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
O1 B1 N1 105.2(4) . . ?
O1 B1 C1 117.8(4) . . ?
O2 B1 O1 106.4(4) . . ?
O2 B1 N1 104.6(4) . . ?
O2 B1 C1 112.6(4) . . ?
C1 B1 N1 109.3(3) . . ?
C8 C9 H9 122.4 . . ?
C8 C9 C10 115.1(5) . . ?
C10 C9 H9 122.4 . . ?
C12 C11 H11 118.3 . . ?
C12 C11 C10 123.4(6) . . ?
C10 C11 H11 118.3 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(6) . . ?
C11 C10 H10 119.8 . . ?
C16 C15 C14 117.5(6) . . ?
C16 C15 N2B 109.6(7) . 3_777 ?
C16 C15 N2A 150.2(11) . . ?
C14 C15 N2B 132.8(8) . 3_777 ?
C14 C15 N2A 92.0(11) . . ?
N2B N2B C15 108.6(15) 3_777 3_777 ?
N2A N2A C15 93(2) 3_777 . ?

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 C8 C9 C10 -178.9(4) . . . . ?
O2 C7 C8 O1 0.7(5) . . . . ?
O2 C7 C8 C9 -178.5(4) . . . . ?
O2 C7 C12 C11 178.3(5) . . . . ?
N1 C17 C16 C15 0.3(8) . . . . ?
N1 C13 C14 C15 -0.6(8) . . . . ?
F2 C4 C3 C2 178.2(3) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C1 C2 F1 -179.8(3) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 B1 O1 -123.9(3) . . . . ?
C6 C1 B1 O2 0.5(4) . . . . ?
C6 C1 B1 N1 116.3(3) . . . . ?
C6 C5 C4 F2 -178.2(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 F1 179.8(3) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 B1 O1 53.1(4) . . . . ?
C2 C1 B1 O2 177.5(3) . . . . ?
C2 C1 B1 N1 -66.7(4) . . . . ?
C7 O2 B1 O1 -11.1(4) . . . . ?
C7 O2 B1 N1 99.9(4) . . . . ?
C7 O2 B1 C1 -141.5(4) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C7 C12 C11 C10 0.0(9) . . . . ?
C8 O1 B1 O2 11.4(4) . . . . ?
C8 O1 B1 N1 -99.2(3) . . . . ?
C8 O1 B1 C1 138.8(4) . . . . ?
C8 C7 C12 C11 -0.7(7) . . . . ?
C8 C9 C10 C11 -0.9(8) . . . . ?
C17 N1 C13 C14 0.3(7) . . . . ?
C17 N1 B1 O1 -21.9(5) . . . . ?
C17 N1 B1 O2 -133.8(4) . . . . ?
C17 N1 B1 C1 105.5(5) . . . . ?
C17 C16 C15 C14 -0.5(8) . . . . ?
C17 C16 C15 N2B -176.3(6) . . . 3_777 ?
C17 C16 C15 N2A 170(2) . . . . ?
C13 N1 C17 C16 -0.2(7) . . . . ?
C13 N1 B1 O1 157.1(4) . . . . ?
C13 N1 B1 O2 45.2(5) . . . . ?
C13 N1 B1 C1 -75.6(5) . . . . ?
C13 C14 C15 C16 0.7(9) . . . . ?
C13 C14 C15 N2B 175.2(7) . . . 3_777 ?
C13 C14 C15 N2A -174.5(10) . . . . ?
C16 C15 N2A N2A 18(4) . . . 3_777 ?
C12 C7 C8 O1 179.8(4) . . . . ?
C12 C7 C8 C9 0.7(7) . . . . ?
C12 C11 C10 C9 0.8(10) . . . . ?
C14 C15 N2A N2A -171(2) . . . 3_777 ?
B1 O1 C8 C7 -7.6(4) . . . . ?
B1 O1 C8 C9 171.5(5) . . . . ?
B1 O2 C7 C8 6.7(5) . . . . ?
B1 O2 C7 C12 -172.4(4) . . . . ?
B1 N1 C17 C16 178.8(4) . . . . ?
B1 N1 C13 C14 -178.7(5) . . . . ?
B1 C1 C6 C5 177.1(3) . . . . ?
B1 C1 C2 F1 3.2(3) . . . . ?
B1 C1 C2 C3 -177.0(3) . . . . ?

_olex2_submission_original_sample_id D-298
_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_I
_database_code_depnum_ccdc_archive 'CCDC 1998623'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;
_audit_creation_date             2020-04-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
gonzalo-campillo-alvarado@uiowa.edu
dale-swenson@uiowa.edu
''
hugom@uaem.mx
hhopfl@uaem.mx
len-macgillivray@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        
"2,4-difluorophenylboronic acid catechol ester adduct of 4,4,'-azopyridine"
_chemical_formula_moiety         'C34 H22 B2 F4 N4 O4, 0.5(C6 H6)'
_chemical_formula_sum            'C37 H25 B2 F4 N4 O4'
_chemical_formula_weight         687.23
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6124(13)
_cell_length_b                   15.3927(15)
_cell_length_c                   17.4936(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.945(5)
_cell_angle_gamma                90
_cell_volume                     3265.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    190.15
_cell_measurement_theta_max      22.22
_cell_measurement_theta_min      2.4215
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0570 before and 0.0498 after correction.
The Ratio of minimum to maximum transmission is 0.9504.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1412
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         2.675
_diffrn_ambient_temperature      190.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_measurement_method       ?
_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                3916
_reflns_number_total             6620
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6620
_refine_ls_number_restraints     511
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.062
_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)+(0.0941P)²+4.3237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.2171
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C35-C36 \\sim C36-C37 \\sim C37-C38 \\sim C38-C39 \\sim C39-C40 \\sim C40-C35
 with sigma of 0.02
 C35-C39 \\sim C35-C39 \\sim C38-C36 \\sim C38-C40 \\sim C40-C36 \\sim C39-C37
 with sigma of 0.04
3. Restrained planarity
 C35, C36, C37, C38, C39, C40
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C35, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C37, C38, C39, C40, C36, C35
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: C38(0.5) H38(0.5) C39(0.5) H39(0.5) C40(0.5) H40(0.5) C35(0.5)
 H35(0.5) C36(0.5) H36(0.5) C37(0.5) H37(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C31(H31), C22(H22), C34(H34), C12(H12), C16(H16),
 C17(H17), C33(H33), C21(H21), C18(H18), C28(H28), C19(H19), C9(H9), C6(H6),
 C3(H3), C4(H4), C25(H25), C5(H5), C11(H11), C26(H26), C27(H27), C38(H38),
 C39(H39), C40(H40), C35(H35), C36(H36), C37(H37)
7.b Fitted hexagon refined as free rotating group:
 C38(C39,C40,C35,C36,C37)
;
_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
F3 F -0.20327(17) 0.62305(14) 0.75592(13) 0.0462(5) Uani 1 1 d . . . . .
F4 F -0.44972(19) 0.71023(15) 0.51640(14) 0.0532(6) Uani 1 1 d . . . . .
F1 F 0.69267(19) 0.28338(15) 0.69255(14) 0.0518(5) Uani 1 1 d . . . . .
O2 O 0.4691(2) 0.07020(15) 0.69254(14) 0.0365(4) Uani 1 1 d . . . . .
O3 O -0.05693(19) 0.77601(16) 0.84162(14) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.6210(2) 0.13831(15) 0.78089(15) 0.0365(4) Uani 1 1 d . . . . .
O4 O 0.01625(19) 0.83748(16) 0.74366(15) 0.0369(4) Uani 1 1 d . . . . .
F2 F 0.7300(2) 0.20629(19) 0.44290(16) 0.0702(7) Uani 1 1 d . . . . .
N1 N 0.4627(2) 0.23075(18) 0.70761(17) 0.0327(4) Uani 1 1 d . . . . .
N4 N 0.0332(2) 0.67761(18) 0.76395(17) 0.0327(4) Uani 1 1 d . . . . .
N2 N 0.2425(2) 0.43556(19) 0.70555(17) 0.0333(5) Uani 1 1 d . . . . .
N3 N 0.2457(2) 0.46705(19) 0.77149(18) 0.0354(5) Uani 1 1 d . . . . .
C2 C 0.4868(3) 0.0365(2) 0.7675(2) 0.0348(6) Uani 1 1 d . . . . .
C7 C 0.5952(3) 0.1608(2) 0.6306(2) 0.0357(4) Uani 1 1 d . . . . .
C13 C 0.4815(3) 0.2834(2) 0.7708(2) 0.0316(6) Uani 1 1 d . . . . .
H13 H 0.544920 0.273835 0.814079 0.038 Uiso 1 1 calc R U . . .
C23 C 0.0094(3) 0.8453(2) 0.8720(2) 0.0328(5) Uani 1 1 d . . . . .
C29 C -0.1589(3) 0.7474(2) 0.6929(2) 0.0321(4) Uani 1 1 d . . . . .
C32 C -0.3542(3) 0.7225(2) 0.5739(2) 0.0372(6) Uani 1 1 d . . . . .
C14 C 0.4118(3) 0.3511(2) 0.7750(2) 0.0326(6) Uani 1 1 d . . . . .
H14 H 0.426078 0.387151 0.820776 0.039 Uiso 1 1 calc R U . . .
C1 C 0.5768(3) 0.0766(2) 0.8194(2) 0.0349(6) Uani 1 1 d . . . . .
C30 C -0.2301(3) 0.6798(2) 0.6932(2) 0.0330(6) Uani 1 1 d . . . . .
C15 C 0.3206(3) 0.3653(2) 0.7112(2) 0.0307(5) Uani 1 1 d . . . . .
C31 C -0.3277(3) 0.6642(2) 0.6353(2) 0.0365(6) Uani 1 1 d . . . . .
H31 H -0.373540 0.615963 0.637939 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1694(3) 0.5386(2) 0.7649(2) 0.0325(6) Uani 1 1 d . . . . .
C22 C 0.0637(3) 0.6258(2) 0.8272(2) 0.0358(6) Uani 1 1 d . . . . .
H22 H 0.036655 0.637334 0.871786 0.043 Uiso 1 1 calc R U . . .
C34 C -0.1923(3) 0.8038(2) 0.6287(2) 0.0358(6) Uani 1 1 d . . . . .
H34 H -0.146134 0.851619 0.625253 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5739(3) 0.1058(3) 0.5641(2) 0.0409(7) Uani 1 1 d . . . . .
H12 H 0.526392 0.057446 0.561973 0.049 Uiso 1 1 calc R U . . .
C24 C 0.0534(3) 0.8814(2) 0.8140(2) 0.0352(6) Uani 1 1 d . . . . .
C8 C 0.6664(3) 0.2287(2) 0.6293(2) 0.0373(6) Uani 1 1 d . . . . .
C16 C 0.3014(3) 0.3120(2) 0.6457(2) 0.0378(7) Uani 1 1 d . . . . .
H16 H 0.239821 0.321425 0.600970 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3734(3) 0.2448(2) 0.6466(2) 0.0382(7) Uani 1 1 d . . . . .
H17 H 0.359356 0.206779 0.602118 0.046 Uiso 1 1 calc R U . . .
C33 C -0.2898(3) 0.7931(2) 0.5697(2) 0.0416(7) Uani 1 1 d . . . . .
H33 H -0.311699 0.833609 0.527252 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1328(3) 0.5564(2) 0.8299(2) 0.0389(7) Uani 1 1 d . . . . .
H21 H 0.154994 0.521293 0.876233 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0700(3) 0.6611(3) 0.7004(2) 0.0398(7) Uani 1 1 d . . . . .
H18 H 0.048781 0.698402 0.655473 0.048 Uiso 1 1 calc R U . . .
C28 C 0.0330(3) 0.8803(2) 0.9470(2) 0.0396(7) Uani 1 1 d . . . . .
H28 H 0.002903 0.856336 0.986529 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1380(3) 0.5914(2) 0.6987(2) 0.0381(7) Uani 1 1 d . . . . .
H19 H 0.162575 0.579883 0.653062 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7126(3) 0.2466(3) 0.5683(2) 0.0443(7) Uani 1 1 d . . . . .
H9 H 0.759627 0.295207 0.569750 0.053 Uiso 1 1 calc R U . . .
C10 C 0.6868(3) 0.1903(3) 0.5054(2) 0.0465(7) Uani 1 1 d . . . . .
C6 C 0.6148(3) 0.0527(2) 0.8983(2) 0.0402(7) Uani 1 1 d . . . . .
H6 H 0.676431 0.080431 0.933497 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4295(3) -0.0283(2) 0.7929(2) 0.0396(6) Uani 1 1 d . . . . .
H3 H 0.367000 -0.055173 0.757846 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4679(3) -0.0529(3) 0.8730(2) 0.0436(7) Uani 1 1 d . . . . .
H4 H 0.430339 -0.097536 0.892657 0.052 Uiso 1 1 calc R U . . .
C25 C 0.1228(3) 0.9520(2) 0.8302(2) 0.0408(7) Uani 1 1 d . . . . .
H25 H 0.153544 0.976059 0.791049 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5579(3) -0.0143(2) 0.9237(2) 0.0444(7) Uani 1 1 d . . . . .
H5 H 0.582297 -0.033582 0.977295 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6199(3) 0.1196(3) 0.5009(3) 0.0506(8) Uani 1 1 d . . . . .
H11 H 0.605199 0.081308 0.456624 0.061 Uiso 1 1 calc R U . . .
C26 C 0.1462(3) 0.9867(3) 0.9070(2) 0.0473(8) Uani 1 1 d . . . . .
H26 H 0.193679 1.035555 0.920223 0.057 Uiso 1 1 calc R U . . .
C27 C 0.1024(3) 0.9521(3) 0.9631(2) 0.0454(8) Uani 1 1 d . . . . .
H27 H 0.119682 0.977611 1.014482 0.054 Uiso 1 1 calc R U . . .
B1 B 0.5425(3) 0.1455(3) 0.7024(3) 0.0358(3) Uani 1 1 d . . . . .
B2 B -0.0465(3) 0.7633(3) 0.7608(3) 0.0350(3) Uani 1 1 d . . . . .
C38 C -0.0448(12) 0.5603(6) 0.9946(8) 0.119(3) Uani 0.5 1 d DG U P A -1
H38 H -0.088143 0.611696 0.983992 0.143 Uiso 0.5 1 calc R U P A -1
C39 C -0.0815(10) 0.4851(8) 0.9516(7) 0.127(3) Uani 0.5 1 d DG U P A -1
H39 H -0.149892 0.484958 0.911561 0.152 Uiso 0.5 1 calc R U P A -1
C40 C -0.0181(12) 0.4099(6) 0.9671(8) 0.119(3) Uani 0.5 1 d DG U P A -1
H40 H -0.043127 0.358456 0.937664 0.143 Uiso 0.5 1 calc R U P A -1
C35 C 0.0820(12) 0.4100(6) 1.0256(8) 0.118(3) Uani 0.5 1 d DG U P A -1
H35 H 0.125388 0.358690 1.036199 0.142 Uiso 0.5 1 calc R U P A -1
C36 C 0.1187(10) 0.4853(8) 1.0686(7) 0.122(3) Uani 0.5 1 d DG U P A -1
H36 H 0.187139 0.485426 1.108629 0.147 Uiso 0.5 1 calc R U P A -1
C37 C 0.0553(12) 0.5605(6) 1.0531(7) 0.121(3) Uani 0.5 1 d DG U P A -1
H37 H 0.080375 0.611930 1.082528 0.145 Uiso 0.5 1 calc R U P A -1


_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
F3 C30 1.370(4) . ?
F4 C32 1.353(4) . ?
F1 C8 1.357(4) . ?
O2 C2 1.370(4) . ?
O2 B1 1.463(5) . ?
O3 C23 1.369(4) . ?
O3 B2 1.469(5) . ?
O1 C1 1.367(4) . ?
O1 B1 1.460(5) . ?
O4 C24 1.369(4) . ?
O4 B2 1.466(5) . ?
F2 C10 1.372(4) . ?
N1 C13 1.338(4) . ?
N1 C17 1.339(5) . ?
N1 B1 1.672(5) . ?
N4 C22 1.331(5) . ?
N4 C18 1.341(4) . ?
N4 B2 1.650(5) . ?
N2 N3 1.242(4) . ?
N2 C15 1.447(4) . ?
N3 C20 1.446(4) . ?
C2 C1 1.388(5) . ?
C2 C3 1.375(5) . ?
C7 C12 1.403(5) . ?
C7 C8 1.382(5) . ?
C7 B1 1.591(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(5) . ?
C23 C24 1.398(5) . ?
C23 C28 1.374(5) . ?
C29 C30 1.374(5) . ?
C29 C34 1.390(5) . ?
C29 B2 1.599(6) . ?
C32 C31 1.369(5) . ?
C32 C33 1.371(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(5) . ?
C1 C6 1.381(5) . ?
C30 C31 1.384(5) . ?
C15 C16 1.375(5) . ?
C31 H31 0.9500 . ?
C20 C21 1.368(5) . ?
C20 C19 1.379(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.372(5) . ?
C34 H34 0.9500 . ?
C34 C33 1.382(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.399(5) . ?
C24 C25 1.375(5) . ?
C8 C9 1.377(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(5) . ?
C17 H17 0.9500 . ?
C33 H33 0.9500 . ?
C21 H21 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.379(5) . ?
C28 H28 0.9500 . ?
C28 C27 1.389(5) . ?
C19 H19 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.367(6) . ?
C10 C11 1.366(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.397(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.400(5) . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.359(6) . ?
C27 H27 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.3900 . ?
C38 C37 1.3900 . ?
C39 H39 0.9500 . ?
C39 C40 1.3900 . ?
C40 H40 0.9500 . ?
C40 C35 1.3900 . ?
C35 H35 0.9500 . ?
C35 C36 1.3900 . ?
C36 H36 0.9500 . ?
C36 C37 1.3900 . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 B1 104.8(3) . . ?
C23 O3 B2 105.7(3) . . ?
C1 O1 B1 104.7(3) . . ?
C24 O4 B2 105.7(3) . . ?
C13 N1 C17 118.7(3) . . ?
C13 N1 B1 123.2(3) . . ?
C17 N1 B1 118.0(3) . . ?
C22 N4 C18 119.3(3) . . ?
C22 N4 B2 122.7(3) . . ?
C18 N4 B2 118.0(3) . . ?
N3 N2 C15 112.4(3) . . ?
N2 N3 C20 111.8(3) . . ?
O2 C2 C1 110.2(3) . . ?
O2 C2 C3 128.4(4) . . ?
C3 C2 C1 121.3(3) . . ?
C12 C7 B1 122.5(3) . . ?
C8 C7 C12 114.8(3) . . ?
C8 C7 B1 122.7(3) . . ?
N1 C13 H13 119.0 . . ?
N1 C13 C14 122.1(3) . . ?
C14 C13 H13 119.0 . . ?
O3 C23 C24 110.5(3) . . ?
O3 C23 C28 128.7(3) . . ?
C28 C23 C24 120.8(3) . . ?
C30 C29 C34 115.1(3) . . ?
C30 C29 B2 124.0(3) . . ?
C34 C29 B2 120.9(3) . . ?
F4 C32 C31 117.8(3) . . ?
F4 C32 C33 119.4(3) . . ?
C31 C32 C33 122.8(4) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
O1 C1 C2 111.0(3) . . ?
O1 C1 C6 126.9(3) . . ?
C6 C1 C2 122.1(3) . . ?
F3 C30 C29 117.9(3) . . ?
F3 C30 C31 116.7(3) . . ?
C29 C30 C31 125.3(3) . . ?
C14 C15 N2 125.0(3) . . ?
C16 C15 N2 115.3(3) . . ?
C16 C15 C14 119.7(3) . . ?
C32 C31 C30 115.9(3) . . ?
C32 C31 H31 122.0 . . ?
C30 C31 H31 122.0 . . ?
C21 C20 N3 117.1(3) . . ?
C21 C20 C19 119.6(3) . . ?
C19 C20 N3 123.2(3) . . ?
N4 C22 H22 119.0 . . ?
N4 C22 C21 122.0(3) . . ?
C21 C22 H22 119.0 . . ?
C29 C34 H34 118.7 . . ?
C33 C34 C29 122.6(3) . . ?
C33 C34 H34 118.7 . . ?
C7 C12 H12 118.7 . . ?
C11 C12 C7 122.5(4) . . ?
C11 C12 H12 118.7 . . ?
O4 C24 C23 110.5(3) . . ?
O4 C24 C25 128.0(3) . . ?
C25 C24 C23 121.5(3) . . ?
F1 C8 C7 118.0(3) . . ?
F1 C8 C9 116.6(3) . . ?
C9 C8 C7 125.5(4) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 H16 120.8 . . ?
N1 C17 C16 122.6(4) . . ?
N1 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C32 C33 C34 118.3(4) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N4 C18 H18 119.2 . . ?
N4 C18 C19 121.5(4) . . ?
C19 C18 H18 119.2 . . ?
C23 C28 H28 121.2 . . ?
C23 C28 C27 117.7(4) . . ?
C27 C28 H28 121.2 . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C8 C9 H9 122.0 . . ?
C10 C9 C8 116.0(4) . . ?
C10 C9 H9 122.0 . . ?
C9 C10 F2 117.9(4) . . ?
C11 C10 F2 118.1(4) . . ?
C11 C10 C9 124.0(4) . . ?
C1 C6 H6 121.7 . . ?
C1 C6 C5 116.6(4) . . ?
C5 C6 H6 121.7 . . ?
C2 C3 H3 121.6 . . ?
C2 C3 C4 116.8(4) . . ?
C4 C3 H3 121.6 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C24 C25 H25 121.5 . . ?
C24 C25 C26 117.0(4) . . ?
C26 C25 H25 121.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C12 C11 H11 121.4 . . ?
C10 C11 C12 117.3(4) . . ?
C10 C11 H11 121.4 . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.5(4) . . ?
C27 C26 H26 119.2 . . ?
C28 C27 H27 119.2 . . ?
C26 C27 C28 121.6(4) . . ?
C26 C27 H27 119.2 . . ?
O2 B1 N1 104.9(3) . . ?
O2 B1 C7 114.4(3) . . ?
O1 B1 O2 107.1(3) . . ?
O1 B1 N1 105.7(3) . . ?
O1 B1 C7 115.6(3) . . ?
C7 B1 N1 108.3(3) . . ?
O3 B2 N4 106.8(3) . . ?
O3 B2 C29 116.1(3) . . ?
O4 B2 O3 106.8(3) . . ?
O4 B2 N4 105.8(3) . . ?
O4 B2 C29 112.7(3) . . ?
C29 B2 N4 108.1(3) . . ?
C39 C38 H38 120.0 . . ?
C39 C38 C37 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.0 . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C35 C40 C39 120.0 . . ?
C35 C40 H40 120.0 . . ?
C40 C35 H35 120.0 . . ?
C40 C35 C36 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C37 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 H37 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37 120.0 . . ?

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
F3 C30 C31 C32 178.8(3) . . . . ?
F4 C32 C31 C30 -179.3(3) . . . . ?
F4 C32 C33 C34 -179.4(3) . . . . ?
F1 C8 C9 C10 179.1(3) . . . . ?
O2 C2 C1 O1 0.5(4) . . . . ?
O2 C2 C1 C6 -177.8(3) . . . . ?
O2 C2 C3 C4 177.6(3) . . . . ?
O3 C23 C24 O4 0.7(4) . . . . ?
O3 C23 C24 C25 180.0(3) . . . . ?
O3 C23 C28 C27 -179.2(3) . . . . ?
O1 C1 C6 C5 -178.0(3) . . . . ?
O4 C24 C25 C26 178.3(3) . . . . ?
F2 C10 C11 C12 -178.1(4) . . . . ?
N1 C13 C14 C15 -1.0(5) . . . . ?
N4 C22 C21 C20 -1.7(6) . . . . ?
N4 C18 C19 C20 -0.9(6) . . . . ?
N2 N3 C20 C21 155.1(3) . . . . ?
N2 N3 C20 C19 -28.7(5) . . . . ?
N2 C15 C16 C17 179.0(3) . . . . ?
N3 N2 C15 C14 -19.7(4) . . . . ?
N3 N2 C15 C16 162.5(3) . . . . ?
N3 C20 C21 C22 177.5(3) . . . . ?
N3 C20 C19 C18 -176.0(3) . . . . ?
C2 O2 B1 O1 14.6(3) . . . . ?
C2 O2 B1 N1 -97.4(3) . . . . ?
C2 O2 B1 C7 144.0(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C7 C12 C11 C10 -0.7(6) . . . . ?
C7 C8 C9 C10 -1.7(6) . . . . ?
C13 N1 C17 C16 1.1(5) . . . . ?
C13 N1 B1 O2 119.6(3) . . . . ?
C13 N1 B1 O1 6.5(4) . . . . ?
C13 N1 B1 C7 -117.9(4) . . . . ?
C13 C14 C15 N2 -177.5(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C23 O3 B2 O4 -8.3(4) . . . . ?
C23 O3 B2 N4 104.5(3) . . . . ?
C23 O3 B2 C29 -135.0(3) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
C23 C28 C27 C26 -0.2(6) . . . . ?
C29 C30 C31 C32 -0.9(5) . . . . ?
C29 C34 C33 C32 -1.9(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C1 O1 B1 O2 -14.2(3) . . . . ?
C1 O1 B1 N1 97.2(3) . . . . ?
C1 O1 B1 C7 -143.0(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C1 C6 C5 C4 -1.3(5) . . . . ?
C30 C29 C34 C33 0.2(5) . . . . ?
C30 C29 B2 O3 -59.2(5) . . . . ?
C30 C29 B2 O4 177.1(3) . . . . ?
C30 C29 B2 N4 60.6(4) . . . . ?
C15 N2 N3 C20 178.5(3) . . . . ?
C15 C16 C17 N1 -1.8(6) . . . . ?
C31 C32 C33 C34 2.2(6) . . . . ?
C22 N4 C18 C19 0.5(5) . . . . ?
C22 N4 B2 O3 9.4(4) . . . . ?
C22 N4 B2 O4 122.9(3) . . . . ?
C22 N4 B2 C29 -116.1(3) . . . . ?
C34 C29 C30 F3 -178.4(3) . . . . ?
C34 C29 C30 C31 1.2(5) . . . . ?
C34 C29 B2 O3 119.7(4) . . . . ?
C34 C29 B2 O4 -4.0(5) . . . . ?
C34 C29 B2 N4 -120.5(3) . . . . ?
C12 C7 C8 F1 -178.6(3) . . . . ?
C12 C7 C8 C9 2.2(5) . . . . ?
C12 C7 B1 O2 -0.8(5) . . . . ?
C12 C7 B1 O1 124.3(4) . . . . ?
C12 C7 B1 N1 -117.4(4) . . . . ?
C24 O4 B2 O3 8.7(4) . . . . ?
C24 O4 B2 N4 -104.8(3) . . . . ?
C24 O4 B2 C29 137.4(3) . . . . ?
C24 C23 C28 C27 -0.5(5) . . . . ?
C24 C25 C26 C27 0.2(6) . . . . ?
C8 C7 C12 C11 -0.9(5) . . . . ?
C8 C7 B1 O2 179.9(3) . . . . ?
C8 C7 B1 O1 -55.0(5) . . . . ?
C8 C7 B1 N1 63.3(4) . . . . ?
C8 C9 C10 F2 179.3(3) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C17 N1 C13 C14 0.3(5) . . . . ?
C17 N1 B1 O2 -57.9(4) . . . . ?
C17 N1 B1 O1 -171.0(3) . . . . ?
C17 N1 B1 C7 64.6(4) . . . . ?
C33 C32 C31 C30 -0.9(5) . . . . ?
C21 C20 C19 C18 0.0(5) . . . . ?
C18 N4 C22 C21 0.8(5) . . . . ?
C18 N4 B2 O3 -169.3(3) . . . . ?
C18 N4 B2 O4 -55.7(4) . . . . ?
C18 N4 B2 C29 65.2(4) . . . . ?
C28 C23 C24 O4 -178.3(3) . . . . ?
C28 C23 C24 C25 1.1(5) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C3 C2 C1 O1 179.5(3) . . . . ?
C3 C2 C1 C6 1.2(5) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C25 C26 C27 C28 0.4(6) . . . . ?
B1 O2 C2 C1 -9.5(4) . . . . ?
B1 O2 C2 C3 171.7(3) . . . . ?
B1 O1 C1 C2 8.7(4) . . . . ?
B1 O1 C1 C6 -173.1(3) . . . . ?
B1 N1 C13 C14 -177.2(3) . . . . ?
B1 N1 C17 C16 178.7(3) . . . . ?
B1 C7 C12 C11 179.7(4) . . . . ?
B1 C7 C8 F1 0.8(5) . . . . ?
B1 C7 C8 C9 -178.4(3) . . . . ?
B2 O3 C23 C24 4.9(4) . . . . ?
B2 O3 C23 C28 -176.3(4) . . . . ?
B2 O4 C24 C23 -5.9(4) . . . . ?
B2 O4 C24 C25 174.8(4) . . . . ?
B2 N4 C22 C21 -177.9(3) . . . . ?
B2 N4 C18 C19 179.3(3) . . . . ?
B2 C29 C30 F3 0.5(5) . . . . ?
B2 C29 C30 C31 -179.8(3) . . . . ?
B2 C29 C34 C33 -178.8(3) . . . . ?
C38 C39 C40 C35 0.0 . . . . ?
C39 C38 C37 C36 0.0 . . . . ?
C39 C40 C35 C36 0.0 . . . . ?
C40 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C37 C38 C39 C40 0.0 . . . . ?

_olex2_submission_original_sample_id I-190
_olex2_submission_special_instructions 'No special instructions were received'
