# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_gb_mm_vd060_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2301453'
loop_
_audit_author_name
_audit_author_address
'Mohand Melaimi'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2023-10-16 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C17 H16 N3 O'
_chemical_formula_sum            'C17 H16 B F4 N3 O'
_chemical_formula_weight         365.14
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8608(3)
_cell_length_b                   9.5883(4)
_cell_length_c                   11.0615(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.807(2)
_cell_angle_gamma                90
_cell_volume                     827.85(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.310
_cell_measurement_theta_min      2.610
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1405 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.9502.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17888
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.609
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3135
_reflns_number_total             3356
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.053
_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)+(0.0274P)²+0.1685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C13(H13), C8(H8), C17(H17), C4(H4), C16(H16), C6(H6), C5(H5),
 C15(H15), C7(H7), C14(H14)
;
_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 0.49311(16) 0.78119(14) 0.38594(11) 0.0252(3) Uani 1 1 d . . . . .
F2 F 0.73533(17) 0.64923(15) 0.39937(12) 0.0323(3) Uani 1 1 d . . . . .
F4 F 0.68998(17) 0.81713(14) 0.25421(12) 0.0296(3) Uani 1 1 d . . . . .
F3 F 0.52846(17) 0.62030(15) 0.23924(12) 0.0326(3) Uani 1 1 d . . . . .
O1 O 0.1223(2) 0.64483(16) 0.63093(13) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.2576(2) 0.44496(19) 0.30451(16) 0.0172(4) Uani 1 1 d . . . . .
N2 N 0.1754(2) 0.55030(19) 0.24509(16) 0.0190(4) Uani 1 1 d . . . . .
N3 N 0.1572(2) 0.63947(19) 0.33274(15) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.2911(3) 0.4684(2) 0.42698(19) 0.0179(4) Uani 1 1 d . . . . .
H1 H 0.348381 0.408446 0.486926 0.022 Uiso 1 1 calc R U . . .
C2 C 0.2239(2) 0.5970(2) 0.44383(18) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.1339(3) 0.7133(2) 0.74147(19) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.3121(3) 0.3269(2) 0.23869(19) 0.0192(5) Uani 1 1 d . . . . .
C13 C 0.0850(3) 0.6346(2) 0.83721(19) 0.0229(5) Uani 1 1 d . . . . .
H13 H 0.049040 0.540630 0.824309 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0923(3) 0.7835(2) 0.32553(19) 0.0208(5) Uani 1 1 d . . . . .
H9A H -0.025312 0.788295 0.282447 0.025 Uiso 1 1 calc R U . . .
H9B H 0.168239 0.845824 0.284764 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2054(3) 0.7070(2) 0.53684(18) 0.0182(4) Uani 1 1 d . . . . .
H11 H 0.319739 0.745399 0.570006 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3382(3) 0.3441(3) 0.1179(2) 0.0236(5) Uani 1 1 d . . . . .
H8 H 0.314651 0.430653 0.077490 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1880(3) 0.8502(2) 0.7587(2) 0.0202(5) Uani 1 1 d . . . . .
H17 H 0.221113 0.903391 0.692974 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3433(3) 0.2024(2) 0.2999(2) 0.0219(5) Uani 1 1 d . . . . .
H4 H 0.320973 0.192654 0.382075 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1927(3) 0.9081(2) 0.8747(2) 0.0244(5) Uani 1 1 d . . . . .
H16 H 0.230749 1.001495 0.888155 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0959(3) 0.8194(2) 0.4615(2) 0.0236(5) Uani 1 1 d . . . . .
H10A H -0.022017 0.820185 0.484506 0.028 Uiso 1 1 calc R U . . .
H10B H 0.146783 0.912933 0.478064 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4363(3) 0.1064(3) 0.1177(2) 0.0284(5) Uani 1 1 d . . . . .
H6 H 0.480847 0.030435 0.076176 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4081(3) 0.0915(2) 0.2385(2) 0.0260(5) Uani 1 1 d . . . . .
H5 H 0.433114 0.005452 0.279239 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1427(3) 0.8318(3) 0.9703(2) 0.0276(5) Uani 1 1 d . . . . .
H15 H 0.144951 0.872914 1.048652 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4000(3) 0.2311(3) 0.0575(2) 0.0282(6) Uani 1 1 d . . . . .
H7 H 0.417285 0.239648 -0.025768 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0892(3) 0.6944(3) 0.9514(2) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.055351 0.641404 1.017055 0.033 Uiso 1 1 calc R U . . .
B1 B 0.6123(3) 0.7157(3) 0.3182(2) 0.0199(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 B1 1.414(3) . ?
F2 B1 1.393(3) . ?
F4 B1 1.387(3) . ?
F3 B1 1.378(3) . ?
O1 C12 1.381(3) . ?
O1 C11 1.423(3) . ?
N1 N2 1.330(3) . ?
N1 C1 1.368(3) . ?
N1 C3 1.438(3) . ?
N2 N3 1.313(2) . ?
N3 C2 1.341(3) . ?
N3 C9 1.471(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.363(3) . ?
C2 C11 1.492(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.385(3) . ?
C3 C8 1.386(3) . ?
C3 C4 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.540(3) . ?
C11 H11 1.0000 . ?
C11 C10 1.558(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.380(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.387(3) . ?
C6 C7 1.382(4) . ?
C5 H5 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.392(4) . ?
C7 H7 0.9500 . ?
C14 H14 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
C12 O1 C11 117.39(16) . . ?
N2 N1 C1 112.94(18) . . ?
N2 N1 C3 120.27(17) . . ?
C1 N1 C3 126.64(18) . . ?
N3 N2 N1 102.63(16) . . ?
N2 N3 C2 114.45(18) . . ?
N2 N3 C9 129.69(17) . . ?
C2 N3 C9 115.48(18) . . ?
N1 C1 H1 127.7 . . ?
C2 C1 N1 104.60(19) . . ?
C2 C1 H1 127.7 . . ?
N3 C2 C1 105.38(19) . . ?
N3 C2 C11 110.96(19) . . ?
C1 C2 C11 143.6(2) . . ?
O1 C12 C13 114.86(19) . . ?
O1 C12 C17 124.0(2) . . ?
C17 C12 C13 121.1(2) . . ?
C8 C3 N1 118.8(2) . . ?
C4 C3 N1 118.58(19) . . ?
C4 C3 C8 122.6(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
N3 C9 H9A 111.6 . . ?
N3 C9 H9B 111.6 . . ?
N3 C9 C10 100.99(17) . . ?
H9A C9 H9B 109.4 . . ?
C10 C9 H9A 111.6 . . ?
C10 C9 H9B 111.6 . . ?
O1 C11 C2 107.41(17) . . ?
O1 C11 H11 110.9 . . ?
O1 C11 C10 114.09(17) . . ?
C2 C11 H11 110.9 . . ?
C2 C11 C10 102.31(16) . . ?
C10 C11 H11 110.9 . . ?
C3 C8 H8 121.0 . . ?
C3 C8 C7 118.1(2) . . ?
C7 C8 H8 121.0 . . ?
C12 C17 H17 120.7 . . ?
C12 C17 C16 118.6(2) . . ?
C16 C17 H17 120.7 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C9 C10 C11 108.21(18) . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
F2 B1 F1 108.36(18) . . ?
F4 B1 F1 108.6(2) . . ?
F4 B1 F2 109.63(19) . . ?
F3 B1 F1 109.48(19) . . ?
F3 B1 F2 110.4(2) . . ?
F3 B1 F4 110.37(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 C14 -178.9(2) . . . . ?
O1 C12 C17 C16 179.4(2) . . . . ?
O1 C11 C10 C9 -128.19(19) . . . . ?
N1 N2 N3 C2 0.4(2) . . . . ?
N1 N2 N3 C9 172.85(19) . . . . ?
N1 C1 C2 N3 0.0(2) . . . . ?
N1 C1 C2 C11 -176.0(3) . . . . ?
N1 C3 C8 C7 176.54(19) . . . . ?
N1 C3 C4 C5 -175.31(18) . . . . ?
N2 N1 C1 C2 0.3(2) . . . . ?
N2 N1 C3 C8 24.1(3) . . . . ?
N2 N1 C3 C4 -158.52(19) . . . . ?
N2 N3 C2 C1 -0.2(2) . . . . ?
N2 N3 C2 C11 177.22(17) . . . . ?
N2 N3 C9 C10 176.32(19) . . . . ?
N3 C2 C11 O1 126.22(18) . . . . ?
N3 C2 C11 C10 5.8(2) . . . . ?
N3 C9 C10 C11 14.1(2) . . . . ?
C1 N1 N2 N3 -0.4(2) . . . . ?
C1 N1 C3 C8 -151.0(2) . . . . ?
C1 N1 C3 C4 26.3(3) . . . . ?
C1 C2 C11 O1 -58.0(4) . . . . ?
C1 C2 C11 C10 -178.4(3) . . . . ?
C2 N3 C9 C10 -11.3(2) . . . . ?
C2 C11 C10 C9 -12.5(2) . . . . ?
C12 O1 C11 C2 162.25(17) . . . . ?
C12 O1 C11 C10 -85.1(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C12 C17 C16 C15 -0.8(3) . . . . ?
C3 N1 N2 N3 -176.16(17) . . . . ?
C3 N1 C1 C2 175.73(18) . . . . ?
C3 C8 C7 C6 -1.0(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C9 N3 C2 C1 -173.80(17) . . . . ?
C9 N3 C2 C11 3.6(2) . . . . ?
C11 O1 C12 C13 -166.22(17) . . . . ?
C11 O1 C12 C17 14.4(3) . . . . ?
C8 C3 C4 C5 1.9(3) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C17 C16 C15 C14 0.9(4) . . . . ?
C4 C3 C8 C7 -0.7(3) . . . . ?
C16 C15 C14 C13 -0.3(4) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C7 C6 C5 C4 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
