# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_perFazop
_database_code_depnum_ccdc_archive 'CCDC 2347086'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-11
_audit_creation_method           
;
Olex2 1.5-ac6-017
(compiled 2024.02.01 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        perfluoroazopyridine
_chemical_formula_moiety         'C10 F8 N4'
_chemical_formula_sum            'C10 F8 N4'
_chemical_formula_weight         328.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H F'
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'
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'

_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                   5.8251(6)
_cell_length_b                   15.5339(18)
_cell_length_c                   5.9792(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.851(12)
_cell_angle_gamma                90
_cell_volume                     531.36(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    914
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      25.1900
_cell_measurement_theta_min      3.5530
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -20 -3 0.0510
7 -4 2 0.0465
-6 14 1 0.0202
-3 -17 -4 0.0486
6 -13 -2 0.0487
8 -5 1 0.0450
-6 12 4 0.0428
-1 12 7 0.0592
0 10 7 0.0647
-5 12 5 0.0529
0 8 8 0.0688
6 -8 -5 0.0698
3 -5 -8 0.0870
0 -1 8 0.0746
0 3 -8 0.0792
0 -7 8 0.0749
8 -2 -2 0.0527
2 7 -8 0.0772
1 -11 7 0.0731
0 11 -7 0.0659
-7 4 -2 0.0202
-1 20 3 0.0298
1 15 -6 0.0603
8 4 -2 0.0546
0 21 -2 0.0275
6 13 0 0.0363
1 22 -1 0.0219
0 22 0 0.0158
0 -22 0 0.0252
2 21 0 0.0187
0 22 1 0.0143
-8 4 -1 0.0187

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.2388 -20.1421 -2.7564 0.8963 -0.2912 0.3344
7.4917 -3.8341 1.6297 -0.0317 0.0103 0.9994
-6.1653 14.4106 0.5806 -0.5106 0.1659 -0.8437
-3.1221 -16.5558 -3.7787 0.8788 -0.2855 -0.3824
6.4294 -13.4194 -2.1952 0.6051 -0.0000 0.7962
7.5088 -5.0532 1.3206 0.0345 -0.0000 0.9994
-6.4216 12.2177 3.5618 -0.6737 -0.1432 -0.7250
-0.6513 12.4648 6.8879 -0.9728 -0.2068 0.1047
-0.2888 10.0885 7.3869 -0.9335 -0.3033 0.1915
-5.4393 11.8493 5.3443 -0.8081 -0.2626 -0.5274
-0.1286 7.7821 7.7534 -0.8850 -0.3940 0.2478
6.3466 -8.3844 -5.4244 0.6928 0.4000 0.6000
3.0902 -5.2649 -8.0031 0.8070 0.5863 0.0712
-0.1296 -1.1068 8.2929 -0.6260 -0.6952 0.3534
-0.0599 3.3490 -8.1725 0.5409 0.7444 -0.3916
0.0712 -7.4400 7.7792 -0.3703 -0.8317 0.4138
8.1914 -1.5744 -1.8527 0.1674 0.3760 0.9114
1.9176 6.8404 -8.0009 0.4000 0.8985 -0.1807
1.0987 -11.0862 6.8514 -0.1763 -0.8295 0.5300
0.1101 11.2051 -7.1438 0.1906 0.8967 -0.3996
-7.4865 4.4955 -1.5152 -0.0000 -0.0000 -1.0000
-0.8901 20.2365 3.1837 -0.9394 0.3052 -0.1560
0.8240 14.6562 -6.2670 0.0000 0.9512 -0.3085
8.0333 4.2190 -2.2141 0.0000 0.5677 0.8232
0.0074 21.2660 -1.9896 -0.5639 0.7761 -0.2822
6.4902 13.1353 -0.2808 -0.4515 0.6215 0.6402
0.8515 21.6707 -0.9759 -0.6624 0.7357 -0.1414
0.1286 21.8854 -0.2010 -0.7287 0.6561 -0.1961
-0.2208 -21.8813 0.1829 0.7304 -0.6577 0.1843
2.2445 20.9724 0.2235 -0.7406 0.6668 0.0830
-0.3459 21.8228 0.6126 -0.7898 0.5738 -0.2169
-7.7417 3.6276 -0.9177 -0.0173 -0.0812 -0.9965

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3070
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  58.00   0.50   15.00    --   20.00  54.00 120.00   92
  2  ω     11.00 110.00   0.50   15.00    --   20.00  54.00-150.00  198
  3  ω    -74.00  93.00   0.50   15.00    --   20.00  54.00   0.00  334
  4  ω    -61.00 -28.00   0.50   15.00    --   20.00  54.00  60.00   66
  5  ω     35.00  60.00   0.50   15.00    --   20.00  54.00  60.00   50
  6  ω    -74.00 -48.00   0.50   15.00    --   20.00  54.00-120.00   52
  7  ω     82.00 107.00   0.50   15.00    --   20.00  54.00-120.00   50
  8  ω    -46.00 -21.00   0.50   15.00    --   20.00  54.00 120.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0042121000
_diffrn_orient_matrix_UB_12      -0.0340077000
_diffrn_orient_matrix_UB_13      -0.0800851000
_diffrn_orient_matrix_UB_21      0.0335219000
_diffrn_orient_matrix_UB_22      0.0290541000
_diffrn_orient_matrix_UB_23      -0.0794280000
_diffrn_orient_matrix_UB_31      0.1192585000
_diffrn_orient_matrix_UB_32      -0.0092644000
_diffrn_orient_matrix_UB_33      0.0432414000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                580
_reflns_number_total             931
_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       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.031
_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)+(0.0290P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
F2 F 1.1496(3) 0.56837(13) 0.4312(3) 0.0294(6) Uani 1 1 d . . . . .
F4 F 0.2948(3) 0.69587(13) 0.1123(4) 0.0334(6) Uani 1 1 d . . . . .
F3 F 0.4828(3) 0.58990(13) -0.1630(4) 0.0327(6) Uani 1 1 d . . . . .
F1 F 0.9332(4) 0.67759(13) 0.6694(4) 0.0352(6) Uani 1 1 d . . . . .
N1 N 0.6165(5) 0.68626(17) 0.3881(5) 0.0246(8) Uani 1 1 d . . . . .
N2 N 0.9005(5) 0.51456(19) -0.0322(5) 0.0302(8) Uani 1 1 d . . . . .
C2 C 0.9368(6) 0.5983(2) 0.3368(6) 0.0225(9) Uani 1 1 d . . . . .
C3 C 0.8234(5) 0.5741(2) 0.1197(6) 0.0199(8) Uani 1 1 d . . . . .
C1 C 0.8254(7) 0.6540(2) 0.4595(6) 0.0252(9) Uani 1 1 d . . . . .
C5 C 0.5091(6) 0.6641(2) 0.1844(7) 0.0247(9) Uani 1 1 d . . . . .
C4 C 0.6038(6) 0.6096(2) 0.0445(6) 0.0245(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.345(4) . ?
F4 C5 1.336(4) . ?
F3 C4 1.342(4) . ?
F1 C1 1.345(4) . ?
N1 C1 1.311(4) . ?
N1 C5 1.306(4) . ?
N2 N2 1.237(5) 3_765 ?
N2 C3 1.426(4) . ?
C2 C3 1.393(5) . ?
C2 C1 1.373(5) . ?
C3 C4 1.388(5) . ?
C5 C4 1.376(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 117.1(3) . . ?
N2 N2 C3 115.3(4) 3_765 . ?
F2 C2 C3 122.4(3) . . ?
F2 C2 C1 119.0(3) . . ?
C1 C2 C3 118.6(3) . . ?
C2 C3 N2 128.2(3) . . ?
C4 C3 N2 115.7(3) . . ?
C4 C3 C2 116.1(3) . . ?
F1 C1 C2 119.1(3) . . ?
N1 C1 F1 116.2(3) . . ?
N1 C1 C2 124.8(4) . . ?
F4 C5 C4 119.2(3) . . ?
N1 C5 F4 117.3(3) . . ?
N1 C5 C4 123.5(3) . . ?
F3 C4 C3 120.0(3) . . ?
F3 C4 C5 120.1(3) . . ?
C5 C4 C3 119.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.594
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_tetraFazop
_database_code_depnum_ccdc_archive 'CCDC 2347090'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-11
_audit_creation_method           
;
Olex2 1.5-ac6-017
(compiled 2024.02.01 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3,5-difluoroazopyridine
_chemical_formula_moiety         'C10 H4 F4 N4'
_chemical_formula_sum            'C10 H4 F4 N4'
_chemical_formula_weight         256.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H2 F2 N2'
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'
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'

_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                   5.0686(6)
_cell_length_b                   5.1891(7)
_cell_length_c                   18.590(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.109(12)
_cell_angle_gamma                90
_cell_volume                     488.96(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    99.9(7)
_cell_measurement_theta_max      29.4790
_cell_measurement_theta_min      2.1540
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0222
0 0 1 0.0326
1 0 -2 0.2206
-2 1 -2 0.3146
-1 0 2 0.2313
1 -1 1 0.3373
0 1 2 0.1940
0 -1 2 0.2245

_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0010 0.0002 -0.9982 0.0070 -0.0337 0.0163
0.0010 -0.0002 0.9982 -0.0070 0.0337 -0.0163
1.0061 0.0017 -2.0031 0.0093 -0.0057 0.1596
-2.0237 1.0050 -1.9698 0.1584 -0.1658 -0.2291
-1.0061 -0.0017 2.0031 -0.0093 0.0057 -0.1596
1.0145 -1.0059 0.9784 -0.1468 0.0706 0.1185
-0.0033 1.0064 2.0094 0.1213 0.0920 -0.0406
0.0073 -1.0074 1.9834 -0.1491 0.0426 -0.0248

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2309
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.191
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  69.00   0.50    5.00    --   20.00  54.00   0.00   80
  2  ω    -73.00 -39.00   0.50    5.00    --   20.00  54.00 120.00   68
  3  ω    -26.00  88.00   0.50    5.00    --   20.00  54.00 120.00  228
  4  ω    -74.00 -38.00   0.50    5.00    --   20.00  54.00-180.00   72
  5  ω    -22.00  26.00   0.50    5.00    --   20.00  54.00-180.00   96
  6  ω     70.00  98.00   0.50    5.00    --   20.00  54.00-180.00   56
  7  ω    -74.00 -43.00   0.50    5.00    --   20.00  54.00 -30.00   62
  8  ω    -37.00 -11.00   0.50    5.00    --   20.00  54.00 -30.00   52
  9  ω     82.00 107.00   0.50    5.00    --   20.00  54.00 -30.00   50
 10  ω    -63.00 -36.00   0.50    5.00    --   20.00  54.00   0.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0048188000
_diffrn_orient_matrix_UB_12      0.1343295000
_diffrn_orient_matrix_UB_13      -0.0069335000
_diffrn_orient_matrix_UB_21      0.0613137000
_diffrn_orient_matrix_UB_22      0.0244320000
_diffrn_orient_matrix_UB_23      0.0336610000
_diffrn_orient_matrix_UB_31      0.1258038000
_diffrn_orient_matrix_UB_32      -0.0069612000
_diffrn_orient_matrix_UB_33      -0.0165000000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                705
_reflns_number_total             848
_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       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.019(11)
_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   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.107
_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)+(0.0772P)²+0.0289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1)
;
_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
F9 F 0.2485(2) 0.0625(2) 0.44788(6) 0.0289(4) Uani 1 1 d . . . . .
F8 F 0.9815(2) 0.5851(2) 0.38273(6) 0.0340(5) Uani 1 1 d . . . . .
N6 N 0.6889(3) 0.0327(3) 0.29623(8) 0.0271(5) Uani 1 1 d . . . . .
N7 N 0.5870(3) 0.5202(4) 0.47855(9) 0.0359(6) Uani 1 1 d . . . . .
C4 C 0.4496(3) 0.1304(4) 0.40413(10) 0.0227(5) Uani 1 1 d . . . . .
C3 C 0.6092(4) 0.3440(4) 0.42020(10) 0.0226(5) Uani 1 1 d . . . . .
C5 C 0.4930(4) -0.0173(4) 0.34287(10) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.379623 -0.159341 0.333602 0.030 Uiso 1 1 calc R U . . .
C1 C 0.8484(4) 0.2340(4) 0.31058(9) 0.0246(5) Uani 1 1 d . . . . .
H1 H 0.989089 0.271816 0.278573 0.029 Uiso 1 1 calc R U . . .
C2 C 0.8127(4) 0.3872(4) 0.37083(10) 0.0234(5) 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
F9 C4 1.352(2) . ?
F8 C2 1.355(2) . ?
N6 C5 1.345(2) . ?
N6 C1 1.347(3) . ?
N7 N7 1.208(3) 3_666 ?
N7 C3 1.423(3) . ?
C4 C3 1.404(3) . ?
C4 C5 1.391(3) . ?
C3 C2 1.400(2) . ?
C1 C2 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N6 C1 117.74(16) . . ?
N7 N7 C3 116.8(2) 3_666 . ?
F9 C4 C3 120.83(17) . . ?
F9 C4 C5 117.99(17) . . ?
C5 C4 C3 121.17(18) . . ?
C4 C3 N7 128.53(18) . . ?
C2 C3 N7 117.15(18) . . ?
C2 C3 C4 114.31(18) . . ?
N6 C5 C4 122.66(19) . . ?
N6 C1 C2 121.69(17) . . ?
F8 C2 C3 118.71(17) . . ?
F8 C2 C1 118.90(16) . . ?
C1 C2 C3 122.39(18) . . ?

_olex2_submission_original_sample_id 3,5Fazop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.088
_oxdiff_exptl_absorpt_empirical_full_min 0.686
####################################################################### 
# 
# 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_PhBE-tetraFazop
_database_code_depnum_ccdc_archive 'CCDC 2347088'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-11
_audit_creation_method           
;
Olex2 1.5-ac6-017
(compiled 2024.02.01 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'3,5-difluoroazopyiridine adduct of phenylboronic acid catechol ester'
_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          ?
_chemical_oxdiff_formula         'C H B N F O'
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                   7.0434(4)
_cell_length_b                   12.8068(7)
_cell_length_c                   16.0013(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.123(5)
_cell_angle_gamma                90
_cell_volume                     1428.89(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2934
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      30.0580
_cell_measurement_theta_min      2.0560
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 2 0.0801
2 1 -2 0.0737
1 -2 1 0.0683
-1 2 -1 0.0434
-1 1 -2 0.0296
1 -1 2 0.0606
0 1 2 0.0733
0 -1 -2 0.0452
0 -1 0 0.0679
-1 2 1 0.0760
1 -2 -1 0.0598
0 -2 1 0.0701
0 2 -1 0.0679
0 -1 2 0.0744
1 0 2 0.0515
0 2 1 0.0579

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9904 -0.9947 1.9854 0.0187 -0.0546 0.2086
1.9904 0.9947 -1.9854 -0.0187 0.0546 -0.2086
0.9943 -1.9916 0.9966 -0.0495 0.1522 -0.0057
-0.9943 1.9916 -0.9966 0.0495 -0.1522 0.0057
-0.9934 0.9964 -1.9922 0.1065 -0.1108 0.0131
0.9934 -0.9964 1.9922 -0.1065 0.1108 -0.0131
-0.0015 0.9950 1.9909 -0.0976 -0.0367 0.0104
0.0015 -0.9950 -1.9909 0.0976 0.0367 -0.0104
0.0002 -0.9954 -0.0005 0.0164 0.0462 0.0252
-0.9956 1.9912 0.9939 -0.0317 -0.1428 0.0413
0.9956 -1.9912 -0.9939 0.0317 0.1428 -0.0413
-0.0003 -1.9910 0.9943 -0.0077 0.0971 0.0682
0.0003 1.9910 -0.9943 0.0077 -0.0971 -0.0682
-0.0012 -0.9958 1.9900 -0.0647 0.0557 0.0608
0.9933 -0.0010 1.9927 -0.1229 0.0646 -0.0383
-0.0010 1.9906 0.9961 -0.0734 -0.0876 -0.0326

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 109.00   0.50   60.00    --   20.00  54.00   0.00  348
  2  ω    -65.00  39.00   0.50   60.00    --   20.00  54.00  60.00  208
  3  ω     60.00  92.00   0.50   60.00    --   20.00  54.00  60.00   64
  4  ω    -65.00 -40.00   0.50   60.00    --   20.00  54.00 -60.00   50
  5  ω    -11.00  14.00   0.50   60.00    --   20.00  54.00 -60.00   50
  6  ω     82.00 107.00   0.50   60.00    --   20.00  54.00 -60.00   50
  7  ω    -74.00 -48.00   0.50   60.00    --   20.00  54.00-180.00   52
  8  ω    -17.00   8.00   0.50   60.00    --   20.00  54.00-180.00   50
  9  ω     85.00 110.00   0.50   60.00    --   20.00  54.00-180.00   50
 10  ω     -6.00  20.00   0.50   60.00    --   20.00  54.00 -90.00   52
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0418783000
_diffrn_orient_matrix_UB_12      -0.0164844000
_diffrn_orient_matrix_UB_13      -0.0408099000
_diffrn_orient_matrix_UB_21      0.0553753000
_diffrn_orient_matrix_UB_22      -0.0463993000
_diffrn_orient_matrix_UB_23      0.0047914000
_diffrn_orient_matrix_UB_31      -0.0743680000
_diffrn_orient_matrix_UB_32      -0.0253400000
_diffrn_orient_matrix_UB_33      0.0178116000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1725
_reflns_number_total             2526
_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       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      0.978
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C17(H17), C11(H11), C14(H14), C15(H15), C10(H10),
 C16(H16), C8(H8), C9(H9)
;
_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 0.16034(16) 0.89427(9) 0.86823(7) 0.0269(3) Uani 1 1 d . . . . .
F2 F 0.82246(17) 0.95204(10) 0.93068(8) 0.0379(4) Uani 1 1 d . . . . .
O2 O 0.6735(2) 0.76883(11) 0.64044(9) 0.0241(4) Uani 1 1 d . . . . .
O1 O 0.41223(19) 0.66515(11) 0.66407(9) 0.0241(4) Uani 1 1 d . . . . .
N1 N 0.5516(2) 0.78765(12) 0.77969(10) 0.0198(4) Uani 1 1 d . . . . .
N2 N 0.4395(2) 0.99957(14) 0.96699(10) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.3411(3) 0.87619(16) 0.85629(13) 0.0196(5) Uani 1 1 d . . . . .
C3 C 0.4872(3) 0.92591(15) 0.90641(13) 0.0200(5) Uani 1 1 d . . . . .
C1 C 0.3729(3) 0.80625(15) 0.79436(13) 0.0205(5) Uani 1 1 d . . . . .
H1 H 0.267962 0.771397 0.762211 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3653(3) 0.72561(16) 0.59352(14) 0.0222(5) Uani 1 1 d . . . . .
C6 C 0.7463(3) 0.62098(15) 0.74814(13) 0.0219(5) Uani 1 1 d . . . . .
C13 C 0.5203(3) 0.78707(16) 0.57933(14) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.6706(3) 0.90449(16) 0.88817(14) 0.0259(6) Uani 1 1 d . . . . .
C5 C 0.6994(3) 0.83659(16) 0.82522(13) 0.0249(5) Uani 1 1 d . . . . .
H5 H 0.826027 0.823971 0.813626 0.030 Uiso 1 1 calc R U . . .
C7 C 0.9324(3) 0.61425(16) 0.72895(14) 0.0255(5) Uani 1 1 d . . . . .
H7 H 0.971432 0.660226 0.688007 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1932(3) 0.73067(16) 0.54110(14) 0.0261(6) Uani 1 1 d . . . . .
H17 H 0.087714 0.687888 0.550013 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6976(3) 0.55298(16) 0.80958(14) 0.0263(5) Uani 1 1 d . . . . .
H11 H 0.572160 0.556348 0.824786 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5100(3) 0.85431(17) 0.51229(14) 0.0285(6) Uani 1 1 d . . . . .
H14 H 0.617315 0.894719 0.501923 0.034 Uiso 1 1 calc R U . . .
C15 C 0.3351(3) 0.86061(17) 0.46019(14) 0.0303(6) Uani 1 1 d . . . . .
H15 H 0.322440 0.907218 0.413543 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8249(3) 0.48113(17) 0.84896(15) 0.0305(6) Uani 1 1 d . . . . .
H10 H 0.787325 0.435746 0.890636 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1803(3) 0.80163(16) 0.47404(14) 0.0285(6) Uani 1 1 d . . . . .
H16 H 0.062346 0.809020 0.437568 0.034 Uiso 1 1 calc R U . . .
C8 C 1.0613(3) 0.54264(17) 0.76778(15) 0.0297(6) Uani 1 1 d . . . . .
H8 H 1.187434 0.539633 0.753315 0.036 Uiso 1 1 calc R U . . .
C9 C 1.0085(3) 0.47530(17) 0.82750(15) 0.0330(6) Uani 1 1 d . . . . .
H9 H 1.097067 0.425281 0.853772 0.040 Uiso 1 1 calc R U . . .
B1 B 0.6002(4) 0.70271(19) 0.70268(16) 0.0228(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.334(2) . ?
F2 C4 1.331(2) . ?
O2 C13 1.370(2) . ?
O2 B1 1.456(3) . ?
O1 C12 1.370(2) . ?
O1 B1 1.461(3) . ?
N1 C1 1.334(2) . ?
N1 C5 1.339(2) . ?
N1 B1 1.714(3) . ?
N2 N2 1.260(3) 3_677 ?
N2 C3 1.426(2) . ?
C2 C3 1.369(3) . ?
C2 C1 1.377(3) . ?
C3 C4 1.391(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.375(3) . ?
C6 C7 1.391(3) . ?
C6 C11 1.392(3) . ?
C6 B1 1.572(3) . ?
C13 C14 1.370(3) . ?
C4 C5 1.367(3) . ?
C7 C8 1.376(3) . ?
C17 C16 1.399(3) . ?
C11 C10 1.374(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.370(3) . ?
C10 C9 1.386(3) . ?
C8 C9 1.377(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 B1 105.53(17) . . ?
C12 O1 B1 105.12(16) . . ?
C1 N1 C5 120.08(18) . . ?
C1 N1 B1 121.96(17) . . ?
C5 N1 B1 117.96(16) . . ?
N2 N2 C3 112.3(2) 3_677 . ?
F1 C2 C3 119.27(18) . . ?
F1 C2 C1 118.13(18) . . ?
C3 C2 C1 122.60(19) . . ?
C2 C3 N2 118.42(18) . . ?
C2 C3 C4 115.39(19) . . ?
C4 C3 N2 126.01(19) . . ?
N1 C1 C2 119.74(19) . . ?
O1 C12 C13 110.56(19) . . ?
O1 C12 C17 128.2(2) . . ?
C17 C12 C13 121.2(2) . . ?
C7 C6 C11 116.8(2) . . ?
C7 C6 B1 120.97(19) . . ?
C11 C6 B1 122.22(19) . . ?
O2 C13 C12 110.14(19) . . ?
C14 C13 O2 128.0(2) . . ?
C14 C13 C12 121.9(2) . . ?
F2 C4 C3 120.37(19) . . ?
F2 C4 C5 118.35(19) . . ?
C5 C4 C3 121.3(2) . . ?
N1 C5 C4 120.88(19) . . ?
C8 C7 C6 121.6(2) . . ?
C12 C17 C16 117.0(2) . . ?
C10 C11 C6 122.2(2) . . ?
C13 C14 C15 116.8(2) . . ?
C16 C15 C14 122.0(2) . . ?
C11 C10 C9 119.6(2) . . ?
C15 C16 C17 121.0(2) . . ?
C7 C8 C9 120.3(2) . . ?
C8 C9 C10 119.4(2) . . ?
O2 B1 O1 106.84(18) . . ?
O2 B1 N1 104.41(16) . . ?
O2 B1 C6 115.58(18) . . ?
O1 B1 N1 104.56(16) . . ?
O1 B1 C6 118.10(18) . . ?
C6 B1 N1 105.91(17) . . ?

_olex2_submission_original_sample_id 34Fazop-PhBE
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.864
####################################################################### 
# 
# 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_PhBE-perFazop
_database_code_depnum_ccdc_archive 'CCDC 2347087'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 F8 N4, 0.5(C24 H18 B2 O4)'
_chemical_formula_sum            'C22 H9 B F8 N4 O2'
_chemical_formula_weight         524.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H B N O F '
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2144(12)
_cell_length_b                   7.2948(13)
_cell_length_c                   11.7785(17)
_cell_angle_alpha                81.392(13)
_cell_angle_beta                 77.890(15)
_cell_angle_gamma                85.140(16)
_cell_volume                     515.41(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      28.8290
_cell_measurement_theta_min      2.8290
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             262
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.089
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6510
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.828
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 104.00   0.50   10.00    --   20.00  54.00-150.00   52
  2  ω      3.00  31.00   0.50   10.00    --   20.00  54.00  90.00   56
  3  ω     57.00 106.00   0.50   10.00    --   20.00  54.00  90.00   98
  4  ω    -74.00  26.00   0.50   10.00    --   20.00  54.00 -30.00  200
  5  ω     48.00  97.00   0.50   10.00    --   20.00  54.00 -30.00   98
  6  ω    -71.00 -11.00   0.50   10.00    --   20.00  54.00  30.00  120
  7  ω     40.00  65.00   0.50   10.00    --   20.00  54.00  30.00   50
  8  ω    -73.00  19.00   0.50   10.00    --   20.00  54.00 120.00  184
  9  ω     48.00  74.00   0.50   10.00    --   20.00  54.00 120.00   52
 10  ω    -52.00   1.00   0.50   10.00    --   20.00  54.00-120.00  106
 11  ω    -49.00  83.00   0.50   10.00    --   20.00  54.00-180.00  264
 12  ω    -74.00  56.00   0.50   10.00    --   20.00  54.00 -90.00  260
 13  ω    -47.00 -22.00   0.50   10.00    --   20.00  54.00   0.00   50
 14  ω    -73.00  58.00   0.50   10.00    --   20.00  54.00-150.00  262
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648184000
_diffrn_orient_matrix_UB_12      0.0129942000
_diffrn_orient_matrix_UB_13      -0.0437734000
_diffrn_orient_matrix_UB_21      0.0632167000
_diffrn_orient_matrix_UB_22      -0.0728167000
_diffrn_orient_matrix_UB_23      -0.0273601000
_diffrn_orient_matrix_UB_31      -0.0739669000
_diffrn_orient_matrix_UB_32      -0.0650334000
_diffrn_orient_matrix_UB_33      0.0346338000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1411
_reflns_number_total             2083
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.010
_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)+(0.0795P)²+0.1487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1614
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 B1, O1, C6, C7, H7, C8, H8, C9, H9, C10, H10, C11, H11, O2, C12, C13, H13,
 C14, H14, C15, H15, C16, H16, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Fixed Sof: O1(0.5) C6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5)
 C10(0.5) H10(0.5) C11(0.5) H11(0.5) O2(0.5) C12(0.5) C17(0.5) C16(0.5)
 H16(0.5) C15(0.5) H15(0.5) C14(0.5) H14(0.5) C13(0.5) H13(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C15(H15), C14(H14),
 C13(H13)
4.b Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C12(C17,C16,C15,C14,C13)
;
_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 0.3129(2) 0.5208(2) 0.84445(12) 0.0462(4) Uani 1 1 d . . . . .
F2 F 0.4886(2) 0.62395(18) 0.61444(12) 0.0378(4) Uani 1 1 d . . . . .
F3 F 0.9537(2) 0.2312(2) 0.91299(12) 0.0460(4) Uani 1 1 d . . . . .
F4 F 1.1609(2) 0.31914(19) 0.68939(11) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.6344(3) 0.3759(3) 0.87636(16) 0.0361(5) Uani 1 1 d . . . . .
N2 N 0.9214(3) 0.5499(3) 0.52373(15) 0.0306(5) Uani 1 1 d . . . . .
C1 C 0.5240(4) 0.4721(3) 0.8022(2) 0.0331(6) Uani 1 1 d . . . . .
C2 C 0.6124(4) 0.5271(3) 0.68530(19) 0.0294(5) Uani 1 1 d . . . . .
C3 C 0.8311(3) 0.4763(3) 0.64225(18) 0.0262(5) Uani 1 1 d . . . . .
C4 C 0.9479(3) 0.3722(3) 0.72098(19) 0.0284(5) Uani 1 1 d . . . . .
C5 C 0.8410(4) 0.3282(3) 0.83610(19) 0.0333(6) Uani 1 1 d . . . . .
B1 B 0.000000 1.000000 0.500000 0.0302(7) Uani 1 2 d S . P . .
O1 O 0.2050(5) 0.9530(4) 0.4724(3) 0.0302(7) Uani 0.5 1 d . . P A 1
C6 C 0.1500(8) 1.0375(6) 0.3654(2) 0.0268(10) Uani 0.5 1 d G . P A 1
C7 C 0.3726(8) 0.9837(5) 0.3376(4) 0.0272(10) Uani 0.5 1 d G . P A 1
H7 H 0.445545 0.921555 0.396919 0.033 Uiso 0.5 1 calc R U P A 1
C8 C 0.4886(4) 1.0208(6) 0.2229(5) 0.0328(12) Uani 0.5 1 d G . P A 1
H8 H 0.640784 0.984076 0.203884 0.039 Uiso 0.5 1 calc R U P A 1
C9 C 0.3819(9) 1.1118(6) 0.1361(2) 0.0349(13) Uani 0.5 1 d G . P A 1
H9 H 0.461212 1.137167 0.057726 0.042 Uiso 0.5 1 calc R U P A 1
C10 C 0.1593(9) 1.1656(6) 0.1639(4) 0.0338(13) Uani 0.5 1 d G . P A 1
H10 H 0.086398 1.227737 0.104600 0.041 Uiso 0.5 1 calc R U P A 1
C11 C 0.0433(4) 1.1284(7) 0.2786(5) 0.0255(11) Uani 0.5 1 d G . P A 1
H11 H -0.108846 1.165218 0.297635 0.031 Uiso 0.5 1 calc R U P A 1
O2 O 0.1066(4) 0.9209(4) 0.5916(2) 0.0268(7) Uani 0.5 1 d . . P A 2
C12 C 0.0667(5) 1.0865(7) 0.3176(4) 0.0256(11) Uani 0.5 1 d G . P B 2
C17 C 0.2553(9) 1.0099(5) 0.3564(2) 0.0267(10) Uani 0.5 1 d G . P B 2
C16 C 0.4558(6) 1.0030(6) 0.2777(5) 0.0306(11) Uani 0.5 1 d G . P B 2
H16 H 0.584662 0.950642 0.304184 0.037 Uiso 0.5 1 calc R U P B 2
C15 C 0.4675(5) 1.0727(6) 0.1602(4) 0.0334(12) Uani 0.5 1 d G . P B 2
H15 H 0.604525 1.067999 0.106399 0.040 Uiso 0.5 1 calc R U P B 2
C14 C 0.2789(9) 1.1493(5) 0.12141(19) 0.0325(12) Uani 0.5 1 d G . P B 2
H14 H 0.286997 1.196968 0.041117 0.039 Uiso 0.5 1 calc R U P B 2
C13 C 0.0785(6) 1.1562(7) 0.2001(4) 0.0278(11) Uani 0.5 1 d G . P B 2
H13 H -0.050397 1.208579 0.173620 0.033 Uiso 0.5 1 calc R U P B 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 C1 1.340(2) . ?
F2 C2 1.338(2) . ?
F3 C5 1.342(3) . ?
F4 C4 1.338(2) . ?
N1 C1 1.308(3) . ?
N1 C5 1.309(3) . ?
N2 N2 1.253(3) 2_766 ?
N2 C3 1.432(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.382(3) . ?
B1 O1 1.277(3) 2_576 ?
B1 O1 1.277(3) . ?
B1 C6 1.658(2) . ?
B1 C6 1.658(2) 2_576 ?
B1 O2 1.409(3) . ?
B1 O2 1.409(3) 2_576 ?
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C7 H7 0.9500 . ?
C7 C8 1.3900 . ?
C8 H8 0.9500 . ?
C8 C9 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3900 . ?
C11 H11 0.9500 . ?
O2 C12 1.348(3) 2_576 ?
C12 C17 1.3900 . ?
C12 C13 1.3900 . ?
C17 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3900 . ?
C15 H15 0.9500 . ?
C15 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 H13 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
C1 N1 C5 117.30(19) . . ?
N2 N2 C3 113.0(2) 2_766 . ?
F1 C1 C2 119.0(2) . . ?
N1 C1 F1 116.8(2) . . ?
N1 C1 C2 124.2(2) . . ?
F2 C2 C1 120.8(2) . . ?
F2 C2 C3 120.53(19) . . ?
C1 C2 C3 118.7(2) . . ?
C2 C3 N2 116.78(19) . . ?
C2 C3 C4 117.11(19) . . ?
C4 C3 N2 125.84(19) . . ?
F4 C4 C3 122.08(19) . . ?
F4 C4 C5 119.3(2) . . ?
C5 C4 C3 118.5(2) . . ?
F3 C5 C4 118.9(2) . . ?
N1 C5 F3 116.9(2) . . ?
N1 C5 C4 124.2(2) . . ?
O1 B1 O1 180.0 2_576 . ?
O1 B1 C6 124.3(2) 2_576 . ?
O1 B1 C6 55.7(2) 2_576 2_576 ?
O1 B1 C6 55.7(2) . . ?
O1 B1 C6 124.3(2) . 2_576 ?
O1 B1 O2 62.70(17) 2_576 2_576 ?
O1 B1 O2 117.30(17) . 2_576 ?
C6 B1 C6 180.0 2_576 . ?
O2 B1 O2 180.00(13) 2_576 . ?
C7 C6 B1 123.1(4) . . ?
C7 C6 C11 120.0 . . ?
C11 C6 B1 116.9(4) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 120.0 . . ?
C10 C11 C6 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 O2 B1 99.9(3) 2_576 . ?
O2 C12 C17 109.7(4) 2_576 . ?
O2 C12 C13 130.3(4) 2_576 . ?
C17 C12 C13 120.0 . . ?
C16 C17 C12 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 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
F1 C1 C2 F2 -1.5(3) . . . . ?
F1 C1 C2 C3 179.93(18) . . . . ?
F2 C2 C3 N2 6.8(3) . . . . ?
F2 C2 C3 C4 -178.70(19) . . . . ?
F4 C4 C5 F3 -0.8(3) . . . . ?
F4 C4 C5 N1 178.9(2) . . . . ?
N1 C1 C2 F2 179.4(2) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
N2 N2 C3 C2 -154.0(2) 2_766 . . . ?
N2 N2 C3 C4 32.1(4) 2_766 . . . ?
N2 C3 C4 F4 -4.6(3) . . . . ?
N2 C3 C4 C5 173.2(2) . . . . ?
C1 N1 C5 F3 179.37(19) . . . . ?
C1 N1 C5 C4 -0.4(4) . . . . ?
C1 C2 C3 N2 -174.6(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 F4 -178.56(19) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 F3 -178.69(19) . . . . ?
C3 C4 C5 N1 1.0(4) . . . . ?
C5 N1 C1 F1 -179.73(19) . . . . ?
C5 N1 C1 C2 -0.6(4) . . . . ?
B1 C6 C7 C8 -179.5(3) . . . . ?
B1 C6 C11 C10 179.6(3) . . . . ?
O1 B1 C6 C7 0.5(3) . . . . ?
O1 B1 C6 C7 -179.5(3) 2_576 . . . ?
O1 B1 C6 C11 -179.1(3) . . . . ?
O1 B1 C6 C11 0.9(3) 2_576 . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C6 0.0 . . . . ?
C11 C6 C7 C8 0.0 . . . . ?
O2 C12 C17 C16 -179.8(4) 2_576 . . . ?
O2 C12 C13 C14 179.7(5) 2_576 . . . ?
C12 C17 C16 C15 0.0 . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C13 C12 C17 C16 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.848
####################################################################### 
# 
# 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_PhBE-azop
_database_code_depnum_ccdc_archive 'CCDC 2347089'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-11
_audit_creation_method           
;
Olex2 1.5-ac6-017
(compiled 2024.02.01 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
"phneylboronicacid catechol ester adduct of 4,4'-bipyridine"
_chemical_formula_moiety         'C34 H26 B2 N4 O4'
_chemical_formula_sum            'C34 H26 B2 N4 O4'
_chemical_formula_weight         576.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H F B N O'
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'

_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                   6.8631(2)
_cell_length_b                   13.1490(3)
_cell_length_c                   15.7054(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.615(3)
_cell_angle_gamma                90
_cell_volume                     1397.39(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5783
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      30.5100
_cell_measurement_theta_min      2.0560
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.1328
0 1 -1 0.1328
0 0 1 0.1192
0 0 -1 0.1539
-1 2 -2 0.1122
1 -2 2 0.0979
-1 2 2 0.1247
1 -2 -2 0.1423
1 -1 1 0.0747
-1 1 -1 0.0933
-1 1 2 0.1191
-2 1 -1 0.0822
1 0 1 0.0895
-1 -1 -1 0.1079
2 1 -2 0.1443
1 1 2 0.1062
-2 -1 2 0.1034
0 1 1 0.1165
0 -1 -1 0.1333

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0009 -1.0028 1.0059 -0.0148 0.0655 0.0233
-0.0009 1.0028 -1.0059 0.0148 -0.0655 -0.0233
-0.0000 0.0001 1.0023 -0.0137 0.0144 0.0414
0.0000 -0.0001 -1.0023 0.0137 -0.0144 -0.0414
-1.0044 2.0076 -2.0201 0.1338 -0.1246 -0.0342
1.0044 -2.0076 2.0201 -0.1338 0.1246 0.0342
-1.0045 2.0079 1.9890 0.0792 -0.0668 0.1313
1.0045 -2.0079 -1.9890 -0.0792 0.0668 -0.1313
1.0035 -1.0048 1.0142 -0.1190 0.0591 0.0109
-1.0035 1.0048 -1.0142 0.1190 -0.0591 -0.0109
-1.0036 1.0050 1.9926 0.0780 -0.0158 0.1132
-2.0061 1.0068 -1.0225 0.2232 -0.0527 0.0016
1.0026 -0.0019 1.0106 -0.1178 0.0081 0.0289
-1.0017 -1.0009 -1.0069 0.1167 0.0429 -0.0470
2.0044 0.9987 -1.9916 -0.1799 -0.0926 -0.0896
1.0016 1.0010 2.0092 -0.1303 -0.0285 0.0883
-2.0044 -0.9987 1.9916 0.1799 0.0926 0.0896
-0.0009 1.0030 0.9986 -0.0125 -0.0366 0.0594
0.0009 -1.0030 -0.9986 0.0125 0.0366 -0.0594

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12564
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.647
_diffrn_reflns_theta_min         2.032
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00 101.00   0.50   30.00    --   20.00  54.00  90.00  264
  2  ω    -74.00 106.50   0.50   30.00    --   20.00  54.00 150.00  361
  3  ω    -47.00 -22.00   0.50   30.00    --   20.00  54.00 -60.00   50
  4  ω     74.00 100.00   0.50   30.00    --   20.00  54.00 -60.00   52
  5  ω    -64.00 -39.00   0.50   30.00    --   20.00  54.00-180.00   50
  6  ω      9.00  35.00   0.50   30.00    --   20.00  54.00-180.00   52
  7  ω    -30.00  -5.00   0.50   30.00    --   20.00  54.00  30.00   50
  8  ω     32.00  57.00   0.50   30.00    --   20.00  54.00  30.00   50
  9  ω     39.00  64.00   0.50   30.00    --   20.00  54.00-120.00   50
 10  ω    -60.00 -35.00   0.50   30.00    --   20.00  54.00  90.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1037949000
_diffrn_orient_matrix_UB_12      0.0010074000
_diffrn_orient_matrix_UB_13      -0.0136233000
_diffrn_orient_matrix_UB_21      -0.0065704000
_diffrn_orient_matrix_UB_22      -0.0508288000
_diffrn_orient_matrix_UB_23      0.0144133000
_diffrn_orient_matrix_UB_31      -0.0127195000
_diffrn_orient_matrix_UB_32      0.0181378000
_diffrn_orient_matrix_UB_33      0.0412671000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3326
_reflns_number_total             4129
_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       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.112a 64-bit (release 01-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4129
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.039
_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)+(0.0579P)²+0.8719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1442
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-C13 \\sim N1B-C13B
 with sigma of 0.02
 N1-C17 \\sim N1B-C17B
 with sigma of 0.02
 N1-B1 \\sim N1B-B1
 with sigma of 0.02
 C13-C14 \\sim C13B-C14B
 with sigma of 0.02
 C17-C16 \\sim C17B-C16B
 with sigma of 0.02
 C15-C14 \\sim C15B-C14B
 with sigma of 0.02
 C15-C16 \\sim C15B-C16B
 with sigma of 0.02
 C15-N2B \\sim C15B-N2B
 with sigma of 0.02
 N1-C14 \\sim N1B-C14B
 with sigma of 0.04
 N1-C16 \\sim N1B-C16B
 with sigma of 0.04
 C13-C17 \\sim C13B-C17B
 with sigma of 0.04
 C13-C15 \\sim C13B-C15B
 with sigma of 0.04
 C13-B1 \\sim C13B-B1
 with sigma of 0.04
 C17-C15 \\sim C17B-C15B
 with sigma of 0.04
 C17-B1 \\sim C17B-B1
 with sigma of 0.04
 C14-C16 \\sim C14B-C16B
 with sigma of 0.04
 C14-N2B \\sim C14B-N2B
 with sigma of 0.04
 C16-N2B \\sim C16B-N2B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N1B)
Uanis(C17B) = Uanis(C17)
Uanis(C16B) = Uanis(C16)
Uanis(C15B) = Uanis(C15)
Uanis(C14B) = Uanis(C14)
Uanis(C13B) = Uanis(C13)
Uanis(N2B) = Uanis(N2)
4. Others
 Sof(N2B)=1-FVAR(1)
 Sof(N2)=FVAR(1)
 Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(N1B)=Sof(C13B)=
 Sof(H13B)=Sof(C14B)=Sof(H14B)=1-FVAR(2)
 Sof(N1)=Sof(C13)=Sof(H13)=Sof(C17)=Sof(H17)=Sof(C15)=Sof(C14)=Sof(H14)=
 Sof(C16)=Sof(H16)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C5(H5), C13(H13), C3(H3), C9(H9), C10(H10), C8(H8),
 C17(H17), C11(H11), C4(H4), C14(H14), C16(H16), C16B(H16B), C17B(H17B),
 C13B(H13B), C14B(H14B)
;
_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
O2 O 0.65904(15) 0.76808(8) 0.63976(6) 0.0244(2) Uani 1 1 d . . . . .
O1 O 0.38372(15) 0.66974(8) 0.66048(6) 0.0247(2) Uani 1 1 d . . . . .
N1 N 0.5346(3) 0.78150(18) 0.78192(16) 0.0185(4) Uani 0.829(5) 1 d D . P A 1
C1 C 0.3371(2) 0.73073(11) 0.58969(9) 0.0244(3) Uani 1 1 d . . . . .
C6 C 0.5009(2) 0.78854(11) 0.57682(9) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.7298(2) 0.61849(11) 0.74518(9) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.9138(2) 0.60716(12) 0.72010(10) 0.0276(3) Uani 1 1 d . . . . .
H12 H 0.949097 0.651393 0.677339 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1558(2) 0.74093(12) 0.53560(10) 0.0294(3) Uani 1 1 d . . . . .
H2 H 0.044008 0.701956 0.543951 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4924(2) 0.85545(12) 0.50939(10) 0.0294(3) Uani 1 1 d . . . . .
H5 H 0.605327 0.892751 0.499792 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3522(3) 0.80082(19) 0.79656(16) 0.0225(4) Uani 0.829(5) 1 d D . P A 1
H13 H 0.243390 0.767168 0.762787 0.027 Uiso 0.829(5) 1 calc R U P A 1
C3 C 0.1462(2) 0.81138(13) 0.46830(10) 0.0316(3) Uani 1 1 d . . . . .
H3 H 0.024399 0.821709 0.430625 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8164(3) 0.47854(12) 0.84512(10) 0.0315(3) Uani 1 1 d . . . . .
H9 H 0.782125 0.434701 0.888380 0.038 Uiso 1 1 calc R U . . .
C10 C 0.9983(3) 0.46795(12) 0.81816(11) 0.0338(4) Uani 1 1 d . . . . .
H10 H 1.088303 0.416588 0.842265 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6849(2) 0.55296(12) 0.80898(9) 0.0267(3) Uani 1 1 d . . . . .
H8 H 0.561354 0.559455 0.828144 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6885(3) 0.82999(19) 0.83001(15) 0.0265(4) Uani 0.829(5) 1 d D . P A 1
H17 H 0.817843 0.817272 0.818487 0.032 Uiso 0.829(5) 1 calc R U P A 1
C11 C 1.0467(2) 0.53336(13) 0.75560(11) 0.0324(3) Uani 1 1 d . . . . .
H11 H 1.171188 0.527504 0.737124 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4756(4) 0.91636(13) 0.91017(11) 0.0201(4) Uani 0.829(5) 1 d D . P A 1
C4 C 0.3107(3) 0.86620(13) 0.45563(10) 0.0330(3) Uani 1 1 d . . . . .
H4 H 0.299363 0.912682 0.408758 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3176(4) 0.86886(15) 0.85990(12) 0.0225(4) Uani 0.829(5) 1 d D . P A 1
H14 H 0.186418 0.882596 0.868560 0.027 Uiso 0.829(5) 1 calc R U P A 1
C16 C 0.6659(4) 0.89703(16) 0.89497(13) 0.0282(4) Uani 0.829(5) 1 d D . P A 1
H16 H 0.777059 0.929129 0.928423 0.034 Uiso 0.829(5) 1 calc R U P A 1
B1 B 0.5805(2) 0.70393(12) 0.70240(9) 0.0206(3) Uani 1 1 d D . . . .
N2 N 0.5739(2) 1.01516(12) 1.02523(11) 0.0250(4) Uani 0.846(4) 1 d . . P B 1
N2B N 0.5858(13) 0.9869(7) 0.9912(6) 0.0250(4) Uani 0.154(4) 1 d . . P A 2
C15B C 0.569(2) 0.9186(7) 0.9165(6) 0.0201(4) Uani 0.171(5) 1 d D . P A 2
C16B C 0.7450(18) 0.8930(9) 0.8943(7) 0.0282(4) Uani 0.171(5) 1 d D . P A 2
H16B H 0.865158 0.919623 0.924994 0.034 Uiso 0.171(5) 1 calc R U P A 2
C17B C 0.7451(17) 0.8265(12) 0.8253(9) 0.0265(4) Uani 0.171(5) 1 d D . P A 2
H17B H 0.866927 0.804678 0.810357 0.032 Uiso 0.171(5) 1 calc R U P A 2
N1B N 0.5750(18) 0.7932(11) 0.7799(9) 0.0185(4) Uani 0.171(5) 1 d D . P A 2
C13B C 0.4015(18) 0.8154(11) 0.8035(9) 0.0225(4) Uani 0.171(5) 1 d D . P A 2
H13B H 0.283255 0.786555 0.772945 0.027 Uiso 0.171(5) 1 calc R U P A 2
C14B C 0.3931(19) 0.8824(8) 0.8748(7) 0.0225(4) Uani 0.171(5) 1 d D . P A 2
H14B H 0.271363 0.900536 0.891899 0.027 Uiso 0.171(5) 1 calc R U 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
O2 C6 1.3671(17) . ?
O2 B1 1.4651(17) . ?
O1 C1 1.3649(17) . ?
O1 B1 1.4707(19) . ?
N1 C13 1.334(2) . ?
N1 C17 1.351(3) . ?
N1 B1 1.683(3) . ?
C1 C6 1.400(2) . ?
C1 C2 1.391(2) . ?
C6 C5 1.371(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.394(2) . ?
C7 B1 1.591(2) . ?
C12 C11 1.384(2) . ?
C2 C3 1.399(2) . ?
C5 C4 1.392(2) . ?
C13 C14 1.388(3) . ?
C3 C4 1.381(2) . ?
C9 C10 1.391(2) . ?
C9 C8 1.387(2) . ?
C10 C11 1.387(2) . ?
C17 C16 1.376(3) . ?
C15 C14 1.379(3) . ?
C15 C16 1.390(3) . ?
C15 N2 1.439(2) 3_677 ?
B1 N1B 1.697(11) . ?
N2 N2 1.244(3) 3_677 ?
N2B N2B 1.300(19) 3_677 ?
N2B C15B 1.468(14) . ?
C15B C16B 1.358(11) . ?
C15B C14B 1.357(11) . ?
C16B C17B 1.392(12) . ?
C17B N1B 1.336(13) . ?
N1B C13B 1.337(12) . ?
C13B C14B 1.433(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 B1 105.20(11) . . ?
C1 O1 B1 104.95(11) . . ?
C13 N1 C17 118.82(18) . . ?
C13 N1 B1 122.75(17) . . ?
C17 N1 B1 118.34(15) . . ?
O1 C1 C6 110.60(13) . . ?
O1 C1 C2 128.21(14) . . ?
C2 C1 C6 121.18(14) . . ?
O2 C6 C1 110.41(12) . . ?
O2 C6 C5 127.67(14) . . ?
C5 C6 C1 121.92(14) . . ?
C12 C7 C8 117.17(13) . . ?
C12 C7 B1 120.42(12) . . ?
C8 C7 B1 122.41(13) . . ?
C11 C12 C7 121.96(14) . . ?
C1 C2 C3 116.74(15) . . ?
C6 C5 C4 116.87(15) . . ?
N1 C13 C14 121.61(18) . . ?
C4 C3 C2 121.20(15) . . ?
C8 C9 C10 120.12(15) . . ?
C11 C10 C9 119.13(15) . . ?
C9 C8 C7 121.58(14) . . ?
N1 C17 C16 122.82(18) . . ?
C12 C11 C10 120.02(14) . . ?
C14 C15 C16 119.36(15) . . ?
C14 C15 N2 115.56(18) . 3_677 ?
C16 C15 N2 125.08(19) . 3_677 ?
C3 C4 C5 122.06(15) . . ?
C15 C14 C13 119.34(16) . . ?
C17 C16 C15 118.03(17) . . ?
O2 B1 O1 106.78(11) . . ?
O2 B1 N1 106.55(13) . . ?
O2 B1 C7 114.02(12) . . ?
O2 B1 N1B 97.9(5) . . ?
O1 B1 N1 104.20(12) . . ?
O1 B1 C7 116.84(12) . . ?
O1 B1 N1B 113.8(4) . . ?
C7 B1 N1 107.56(14) . . ?
C7 B1 N1B 106.0(6) . . ?
N2 N2 C15 112.7(2) 3_677 3_677 ?
N2B N2B C15B 112.1(12) 3_677 . ?
C16B C15B N2B 113.6(10) . . ?
C14B C15B N2B 123.2(10) . . ?
C14B C15B C16B 123.2(8) . . ?
C15B C16B C17B 118.1(9) . . ?
N1B C17B C16B 120.5(10) . . ?
C17B N1B B1 119.2(9) . . ?
C17B N1B C13B 121.3(11) . . ?
C13B N1B B1 118.5(9) . . ?
N1B C13B C14B 120.3(10) . . ?
C15B C14B C13B 116.4(9) . . ?

_olex2_submission_original_sample_id BE-azop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.914
####################################################################### 
# 
# 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_diFazop
_database_code_depnum_ccdc_archive 'CCDC 2347092'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-19
_audit_creation_method           
;
Olex2 1.5-ac6-018
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 F2 N4'
_chemical_formula_sum            'C10 H6 F2 N4'
_chemical_formula_weight         220.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
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'
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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.6796(6)
_cell_length_b                   12.6700(7)
_cell_length_c                   22.3037(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1887.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    99.9(7)
_cell_measurement_theta_max      28.4080
_cell_measurement_theta_min      3.1970
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.999
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0418
1 0 0 0.1209
-2 0 1 0.1457
-2 1 1 0.1418
0 0 -1 0.0466
0 1 2 0.0460
0 1 -2 0.0530
0 -1 -2 0.0428
1 0 -2 0.1054
1 1 -2 0.1071
-1 0 -2 0.1194
-1 1 -2 0.1195
1 1 2 0.1137
-1 0 2 0.1365
-1 1 2 0.1289
3 10 -23 0.0718
0 -18 0 0.0218
-4 -2 28 0.0916
0 17 10 0.0451
0 17 -8 0.0475
-1 0 -31 0.0435
0 -18 0 0.0202
1 -1 31 0.0263
-3 3 -30 0.0544
0 -18 3 0.0204
3 2 30 0.0502

_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.063
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 0.9999 0.0047 -0.0026 0.0020 0.0559
1.0007 0.0001 0.0042 0.0595 0.0879 -0.0007
-2.0014 -0.0007 0.9906 -0.0928 -0.1936 0.0033
-2.0011 0.9992 0.9952 -0.0954 -0.1916 0.0591
-0.0001 0.0004 -0.9990 -0.0263 0.0178 -0.0019
0.0004 0.9991 2.0026 0.0499 -0.0336 0.0598
0.0001 1.0008 -1.9933 -0.0552 0.0377 0.0520
-0.0004 -0.9991 -2.0026 -0.0499 0.0336 -0.0598
1.0006 0.0010 -1.9937 0.0070 0.1235 -0.0045
1.0008 1.0009 -1.9891 0.0044 0.1256 0.0513
-1.0008 0.0007 -2.0022 -0.1121 -0.0523 -0.0032
-1.0006 1.0007 -1.9975 -0.1147 -0.0502 0.0527
1.0011 0.9992 2.0068 0.1095 0.0543 0.0591
-1.0006 -0.0010 1.9937 -0.0070 -0.1235 0.0045
-1.0003 0.9989 1.9984 -0.0096 -0.1215 0.0604
3.4425 10.4995 -22.6782 -0.4209 0.7291 0.5397
-0.2600 -17.8585 0.0654 0.0356 -0.0617 -0.9975
-4.1032 -1.9463 28.0508 0.4994 -0.8649 -0.0508
0.1555 16.8433 10.4652 0.2379 -0.1374 0.9615
-0.2533 17.2119 -8.3547 -0.2823 0.1630 0.9454
-0.6774 -0.1801 -31.3363 -0.8638 0.4987 -0.0712
0.0851 -17.8609 0.4568 0.0664 -0.0383 -0.9971
0.6815 -1.0929 31.2770 0.8660 -0.5000 0.0000
-2.6144 2.5481 -29.8599 -0.9476 0.3079 0.0854
0.4311 -17.7788 2.6574 0.1446 -0.0470 -0.9884
2.5846 1.7356 30.0758 0.9397 -0.3053 0.1544

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         3.216
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  76.00   0.50   30.00    --   20.00  54.00   0.00   52
  2  ω    -73.00 108.00   0.50   30.00    --   20.00  54.00-150.00  362
  3  ω    -59.00   6.00   0.50   30.00    --   20.00  54.00-180.00  130
  4  ω     27.00  96.00   0.50   30.00    --   20.00  54.00-180.00  138
  5  ω    -69.00 -36.00   0.50   30.00    --   20.00  54.00 -90.00   66
  6  ω    -34.00  -9.00   0.50   30.00    --   20.00  54.00 -90.00   50
  7  ω      1.00  26.00   0.50   30.00    --   20.00  54.00 -90.00   50
  8  ω     42.00  68.00   0.50   30.00    --   20.00  54.00 -90.00   52
  9  ω    -71.00  47.00   0.50   30.00    --   20.00  54.00 150.00  236
 10  ω    -55.00 -28.00   0.50   30.00    --   20.00  54.00 -60.00   54
 11  ω     55.00  81.00   0.50   30.00    --   20.00  54.00 -60.00   52
 12  ω    -19.00   6.00   0.50   30.00    --   20.00  54.00   0.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0593947000
_diffrn_orient_matrix_UB_12      -0.0027630000
_diffrn_orient_matrix_UB_13      0.0262982000
_diffrn_orient_matrix_UB_21      0.0879101000
_diffrn_orient_matrix_UB_22      0.0021101000
_diffrn_orient_matrix_UB_23      -0.0178279000
_diffrn_orient_matrix_UB_31      -0.0006780000
_diffrn_orient_matrix_UB_32      0.0558704000
_diffrn_orient_matrix_UB_33      0.0019671000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1143
_reflns_number_total             1651
_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       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      0.958
_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)+(0.0977P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1557
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C6(H6), C5(H5), C10(H10), C1(H1)
;
_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
F2 F 0.2108(2) 0.42510(11) 0.58200(6) 0.0410(5) Uani 1 1 d . . . . .
F1 F 0.4157(2) 0.82917(10) 0.76126(6) 0.0405(5) Uani 1 1 d . . . . .
N2 N 0.3744(3) 0.66234(16) 0.68538(8) 0.0266(5) Uani 1 1 d . . . . .
N4 N 0.3548(3) 0.57893(16) 0.65570(8) 0.0287(6) Uani 1 1 d . . . . .
N1 N 0.3711(3) 0.62908(17) 0.87457(9) 0.0322(6) Uani 1 1 d . . . . .
N3 N 0.3115(3) 0.61759(18) 0.46745(9) 0.0324(6) Uani 1 1 d . . . . .
C3 C 0.3757(4) 0.64466(19) 0.74847(10) 0.0249(6) Uani 1 1 d . . . . .
C8 C 0.3471(4) 0.59681(18) 0.59274(10) 0.0251(6) Uani 1 1 d . . . . .
C4 C 0.3561(4) 0.54745(19) 0.77717(11) 0.0268(6) Uani 1 1 d . . . . .
H4 H 0.344174 0.484346 0.754444 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4080(4) 0.68879(19) 0.56347(11) 0.0277(6) Uani 1 1 d . . . . .
H9 H 0.462649 0.746188 0.585446 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2724(4) 0.5169(2) 0.55673(11) 0.0283(6) Uani 1 1 d . . . . .
C6 C 0.2543(4) 0.5285(2) 0.49559(11) 0.0313(7) Uani 1 1 d . . . . .
H6 H 0.200128 0.472123 0.472643 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3544(4) 0.5441(2) 0.83892(11) 0.0302(7) Uani 1 1 d . . . . .
H5 H 0.340348 0.477068 0.857561 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3872(4) 0.6947(2) 0.50188(11) 0.0314(7) Uani 1 1 d . . . . .
H10 H 0.429317 0.757813 0.482606 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3950(4) 0.73190(19) 0.78569(11) 0.0286(6) Uani 1 1 d . . . . .
C1 C 0.3916(4) 0.7226(2) 0.84744(12) 0.0312(7) Uani 1 1 d . . . . .
H1 H 0.404260 0.784396 0.871275 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C7 1.356(3) . ?
F1 C2 1.355(3) . ?
N2 N4 1.254(3) . ?
N2 C3 1.425(3) . ?
N4 C8 1.423(3) . ?
N1 C5 1.343(3) . ?
N1 C1 1.338(3) . ?
N3 C6 1.347(3) . ?
N3 C10 1.342(3) . ?
C3 C4 1.394(3) . ?
C3 C2 1.388(3) . ?
C8 C9 1.396(3) . ?
C8 C7 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C7 C6 1.377(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C2 C1 1.383(4) . ?
C1 H1 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
N4 N2 C3 112.9(2) . . ?
N2 N4 C8 112.99(19) . . ?
C1 N1 C5 116.8(2) . . ?
C10 N3 C6 116.8(2) . . ?
C4 C3 N2 126.3(2) . . ?
C2 C3 N2 117.8(2) . . ?
C2 C3 C4 115.9(2) . . ?
C9 C8 N4 125.7(2) . . ?
C7 C8 N4 117.9(2) . . ?
C7 C8 C9 116.3(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.7(2) . . ?
C10 C9 H9 120.6 . . ?
F2 C7 C8 119.7(2) . . ?
F2 C7 C6 118.5(2) . . ?
C6 C7 C8 121.9(2) . . ?
N3 C6 C7 121.7(2) . . ?
N3 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
N1 C5 C4 124.5(2) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N3 C10 C9 124.5(2) . . ?
N3 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
F1 C2 C3 119.6(2) . . ?
F1 C2 C1 118.7(2) . . ?
C1 C2 C3 121.8(2) . . ?
N1 C1 C2 121.9(2) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?

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
F2 C7 C6 N3 179.7(2) . . . . ?
F1 C2 C1 N1 179.8(2) . . . . ?
N2 N4 C8 C9 17.0(4) . . . . ?
N2 N4 C8 C7 -162.7(2) . . . . ?
N2 C3 C4 C5 -178.0(2) . . . . ?
N2 C3 C2 F1 -1.4(3) . . . . ?
N2 C3 C2 C1 178.0(2) . . . . ?
N4 N2 C3 C4 -0.6(4) . . . . ?
N4 N2 C3 C2 -179.5(2) . . . . ?
N4 C8 C9 C10 -178.7(2) . . . . ?
N4 C8 C7 F2 -0.4(3) . . . . ?
N4 C8 C7 C6 178.2(2) . . . . ?
C3 N2 N4 C8 178.15(18) . . . . ?
C3 C4 C5 N1 -0.2(4) . . . . ?
C3 C2 C1 N1 0.5(4) . . . . ?
C8 C9 C10 N3 0.0(4) . . . . ?
C8 C7 C6 N3 1.1(4) . . . . ?
C4 C3 C2 F1 179.7(2) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
C9 C8 C7 F2 179.8(2) . . . . ?
C9 C8 C7 C6 -1.6(4) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C6 N3 C10 C9 -0.6(4) . . . . ?
C5 N1 C1 C2 0.2(4) . . . . ?
C10 N3 C6 C7 0.0(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C1 N1 C5 C4 -0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.083
_oxdiff_exptl_absorpt_empirical_full_min 0.635
####################################################################### 
# 
# 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_PhBE-diFazop
_database_code_depnum_ccdc_archive 'CCDC 2347091'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-04-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'3-fluoroazopyridine adduct of phenylboronic acid catechol ester'
_chemical_formula_moiety         'C34 H24 B2 F2 N4 O4'
_chemical_formula_sum            'C34 H24 B2 F2 N4 O4'
_chemical_formula_weight         612.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H F O B'
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                   6.8710(3)
_cell_length_b                   13.0541(6)
_cell_length_c                   15.9373(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.627(4)
_cell_angle_gamma                90
_cell_volume                     1416.86(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4824
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      29.9900
_cell_measurement_theta_min      2.0460
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -11 16 0.1055
1 -14 -14 0.1922
4 15 -11 0.0922
-1 15 13 0.2170
-6 -10 14 0.1025
8 -2 10 0.0776
-8 2 -10 0.0326
1 -2 -2 0.2173
-1 1 2 0.1965
0 -2 1 0.1675
0 2 -1 0.1300
1 -1 -1 0.1951
0 -1 1 0.1417
0 1 -1 0.0909
-2 1 1 0.1071
-1 0 1 0.1132
-2 2 -1 0.0885
-2 0 1 0.0899
-2 -1 1 0.0681
0 -1 2 0.1055
1 0 2 0.1017
2 1 2 0.1046
1 1 0 0.1119
1 2 -1 0.1050
0 -1 -1 0.1845
1 -2 0 0.1894
1 -2 1 0.1686
1 -1 0 0.1509
2 -1 0 0.1369
1 1 2 0.1444

_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.6020 -11.0122 15.7932 -0.0220 -0.0382 0.9990
0.8304 -14.4174 -13.9750 -0.4999 -0.8659 -0.0161
4.1153 14.6808 -10.8454 0.1682 0.2913 -0.9417
-0.6894 14.7334 13.4762 0.4999 0.8659 -0.0143
-6.0388 -9.9777 14.4215 -0.1727 0.0561 0.9834
7.8382 -1.8819 10.4356 0.9493 -0.3085 0.0599
-7.9008 1.7548 -10.2396 -0.9500 0.3087 -0.0476
0.9991 -1.9854 -1.9870 0.0031 -0.1623 -0.0395
-0.9976 0.9907 1.9900 -0.0132 0.1189 0.0699
0.0032 -1.9890 1.0040 0.0100 -0.0728 0.0911
-0.0032 1.9890 -1.0040 -0.0100 0.0728 -0.0911
0.9978 -0.9904 -0.9921 0.0432 -0.1048 -0.0397
0.0017 -0.9944 1.0009 0.0200 -0.0293 0.0606
-0.0017 0.9944 -1.0009 -0.0200 0.0293 -0.0606
-1.9944 0.9859 0.9894 -0.1266 0.1521 0.0797
-0.9963 -0.0042 0.9952 -0.0533 0.0614 0.0702
-1.9962 1.9800 -1.0094 -0.1767 0.1673 -0.0112
-1.9929 -0.0087 0.9925 -0.1366 0.1086 0.1101
-1.9914 -1.0034 0.9955 -0.1466 0.0652 0.1405
0.0019 -0.9941 1.9988 0.0501 -0.0152 0.0908
0.9970 0.0051 1.9985 0.1435 -0.0191 0.0205
1.9920 1.0043 1.9982 0.2368 -0.0229 -0.0499
0.9951 0.9992 -0.0003 0.0934 -0.0038 -0.0704
0.9934 1.9936 -1.0013 0.0733 0.0255 -0.1310
0.0013 -0.9950 -0.9949 -0.0401 -0.0575 0.0002
0.9995 -1.9848 0.0088 0.0633 -0.1341 0.0209
0.9997 -1.9845 1.0067 0.0934 -0.1200 0.0511
0.9980 -0.9902 0.0057 0.0733 -0.0907 -0.0095
1.9946 -0.9856 0.0085 0.1566 -0.1380 -0.0495
0.9955 0.9998 1.9955 0.1535 0.0243 -0.0099

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9101
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 107.00   0.50   10.00    --   20.00  54.00-120.00  144
  2  ω    -46.00  68.00   0.50   10.00    --   20.00  54.00-180.00  228
  3  ω     73.00  99.00   0.50   10.00    --   20.00  54.00-180.00   52
  4  ω     12.00 110.00   0.50   10.00    --   20.00  54.00  60.00  196
  5  ω      6.00 102.00   0.50   10.00    --   20.00  54.00 120.00  192
  6  ω     -1.00  24.00   0.50   10.00    --   20.00  54.00-150.00   50
  7  ω     52.00  89.00   0.50   10.00    --   20.00  54.00-150.00   74
  8  ω    -17.00   8.00   0.50   10.00    --   20.00  54.00-120.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0834969000
_diffrn_orient_matrix_UB_12      0.0102956000
_diffrn_orient_matrix_UB_13      0.0301138000
_diffrn_orient_matrix_UB_21      -0.0476710000
_diffrn_orient_matrix_UB_22      0.0436319000
_diffrn_orient_matrix_UB_23      0.0141158000
_diffrn_orient_matrix_UB_31      -0.0400244000
_diffrn_orient_matrix_UB_32      -0.0305498000
_diffrn_orient_matrix_UB_33      0.0302925000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2016
_reflns_number_total             2494
_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       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.112a 64-bit (release 01-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_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         0.484
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.049
_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)+(0.0725P)²+0.4453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1436
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C8(H8), C13(H13), C9(H9), C2(H2), C16(H16), C17(H17),
 C14(H14), C10(H10), C15(H15), C1(H1)
;
_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 0.86305(16) 0.88871(9) 0.12596(7) 0.0290(3) Uani 1 1 d . . . . .
O1 O 0.3338(2) 0.77040(10) 0.35993(8) 0.0241(4) Uani 1 1 d . . . . .
O2 O 0.60780(19) 0.67052(10) 0.33760(8) 0.0232(4) Uani 1 1 d . . . . .
N1 N 0.4627(2) 0.78675(12) 0.21977(10) 0.0210(4) Uani 1 1 d . . . . .
N2 N 0.5733(2) 0.98766(13) 0.02515(10) 0.0257(4) Uani 1 1 d . . . . .
C6 C 0.4891(3) 0.78967(15) 0.42107(12) 0.0222(5) Uani 1 1 d . . . . .
C4 C 0.6774(3) 0.87207(15) 0.13967(12) 0.0203(5) Uani 1 1 d . . . . .
C7 C 0.6518(3) 0.73147(15) 0.40763(12) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.5245(3) 0.92002(15) 0.09016(13) 0.0230(5) Uani 1 1 d . . . . .
C12 C 0.2671(3) 0.62216(15) 0.25416(12) 0.0226(5) Uani 1 1 d . . . . .
C5 C 0.6448(3) 0.80472(15) 0.20302(12) 0.0207(5) Uani 1 1 d . . . . .
H5 H 0.752696 0.770930 0.234925 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4947(3) 0.85643(16) 0.48778(13) 0.0276(5) Uani 1 1 d . . . . .
H11 H 0.382090 0.894378 0.497877 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8280(3) 0.73997(16) 0.45956(12) 0.0256(5) Uani 1 1 d . . . . .
H8 H 0.938896 0.700066 0.450461 0.031 Uiso 1 1 calc R U . . .
C13 C 0.0764(3) 0.61487(16) 0.27487(13) 0.0265(5) Uani 1 1 d . . . . .
H13 H 0.035743 0.660639 0.315500 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8361(3) 0.80982(16) 0.52609(13) 0.0285(5) Uani 1 1 d . . . . .
H9 H 0.955983 0.818884 0.562479 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3360(3) 0.90118(17) 0.10937(14) 0.0285(5) Uani 1 1 d . . . . .
H2 H 0.225748 0.933706 0.078089 0.034 Uiso 1 1 calc R U . . .
C16 C 0.1884(3) 0.48229(16) 0.15507(14) 0.0286(5) Uani 1 1 d . . . . .
H16 H 0.227221 0.437497 0.113334 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3185(3) 0.55435(15) 0.19338(13) 0.0254(5) Uani 1 1 d . . . . .
H17 H 0.446993 0.557697 0.177713 0.031 Uiso 1 1 calc R U . . .
C14 C -0.0548(3) 0.54243(16) 0.23751(14) 0.0285(5) Uani 1 1 d . . . . .
H14 H -0.183392 0.538675 0.252999 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6735(3) 0.86607(16) 0.54019(13) 0.0285(5) Uani 1 1 d . . . . .
H10 H 0.683443 0.912358 0.586561 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0008(3) 0.47576(16) 0.17792(13) 0.0294(5) Uani 1 1 d . . . . .
H15 H -0.088821 0.425676 0.152673 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3114(3) 0.83504(16) 0.17405(14) 0.0276(5) Uani 1 1 d . . . . .
H1 H 0.182387 0.822882 0.187033 0.033 Uiso 1 1 calc R U . . .
B1 B 0.4146(3) 0.70578(17) 0.29785(14) 0.0213(5) 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 C4 1.340(2) . ?
O1 C6 1.369(2) . ?
O1 B1 1.464(3) . ?
O2 C7 1.371(2) . ?
O2 B1 1.467(3) . ?
N1 C5 1.334(2) . ?
N1 C1 1.345(3) . ?
N1 B1 1.698(3) . ?
N2 N2 1.243(3) 3_675 ?
N2 C3 1.434(3) . ?
C6 C7 1.392(3) . ?
C6 C11 1.371(3) . ?
C4 C3 1.377(3) . ?
C4 C5 1.379(3) . ?
C7 C8 1.377(3) . ?
C3 C2 1.392(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.392(3) . ?
C12 B1 1.586(3) . ?
C11 C10 1.397(3) . ?
C8 C9 1.394(3) . ?
C13 C14 1.385(3) . ?
C9 C10 1.380(3) . ?
C2 C1 1.372(3) . ?
C16 C17 1.383(3) . ?
C16 C15 1.388(3) . ?
C14 C15 1.379(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 B1 104.90(15) . . ?
C7 O2 B1 104.98(15) . . ?
C5 N1 C1 119.16(17) . . ?
C5 N1 B1 122.34(15) . . ?
C1 N1 B1 118.50(16) . . ?
N2 N2 C3 112.2(2) 3_675 . ?
O1 C6 C7 110.87(17) . . ?
O1 C6 C11 127.41(18) . . ?
C11 C6 C7 121.72(19) . . ?
F1 C4 C3 120.18(17) . . ?
F1 C4 C5 118.23(17) . . ?
C3 C4 C5 121.58(18) . . ?
O2 C7 C6 110.31(17) . . ?
O2 C7 C8 128.10(19) . . ?
C8 C7 C6 121.58(19) . . ?
C4 C3 N2 117.40(17) . . ?
C4 C3 C2 117.05(19) . . ?
C2 C3 N2 125.52(18) . . ?
C13 C12 B1 120.54(18) . . ?
C17 C12 C13 116.99(19) . . ?
C17 C12 B1 122.46(18) . . ?
N1 C5 C4 120.40(18) . . ?
C6 C11 C10 116.9(2) . . ?
C7 C8 C9 116.93(19) . . ?
C14 C13 C12 121.5(2) . . ?
C10 C9 C8 121.4(2) . . ?
C1 C2 C3 119.17(19) . . ?
C17 C16 C15 119.6(2) . . ?
C16 C17 C12 122.09(19) . . ?
C15 C14 C13 120.21(19) . . ?
C9 C10 C11 121.4(2) . . ?
C14 C15 C16 119.57(19) . . ?
N1 C1 C2 122.58(19) . . ?
O1 B1 O2 106.95(16) . . ?
O1 B1 N1 105.34(15) . . ?
O1 B1 C12 114.54(17) . . ?
O2 B1 N1 105.00(15) . . ?
O2 B1 C12 117.54(17) . . ?
C12 B1 N1 106.37(15) . . ?

_olex2_submission_original_sample_id 3Fazop-PhBE
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.795
