# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_JCK_C32H20BF2N5O4_lowtemp_01192021_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2105103'
loop_
_audit_author_name
_audit_author_address
'Jordan C. Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 B F2 N5 O4'
_chemical_formula_weight         587.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.209(6)
_cell_length_b                   13.821(7)
_cell_length_c                   17.299(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.650(12)
_cell_angle_gamma                90
_cell_volume                     2749(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4762
_cell_measurement_theta_min      2.3051
_cell_measurement_theta_max      25.8109

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            'dark blue, gold'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            33363
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_max         30.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8535
_reflns_number_gt                5252
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.4200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8535
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.38030(15) 0.51039(13) 0.57323(12) 0.0279(4) Uani 1 1 d . . . . .
F2 F 0.36984(8) 0.47575(7) 0.49671(6) 0.0390(3) Uani 1 1 d . . . . .
C2 C 0.36119(12) 0.78254(11) 0.56016(9) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.34339(11) 0.92473(9) 0.48913(8) 0.0436(3) Uani 1 1 d . . . . .
N2 N 0.59484(10) 0.62987(9) 0.65736(8) 0.0247(3) Uani 1 1 d . . . . .
O3 O 0.66889(10) 0.23788(9) 0.77073(7) 0.0385(3) Uani 1 1 d . . . . .
C3 C 0.47911(12) 0.77449(11) 0.60268(9) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.49960(10) 0.47453(9) 0.63663(8) 0.0237(3) Uani 1 1 d . . . . .
N4 N 0.29953(12) 0.87016(10) 0.52620(8) 0.0302(3) Uani 1 1 d . . . . .
O4 O 0.82166(10) 0.29608(10) 0.75080(9) 0.0478(4) Uani 1 1 d . . . . .
C4 C 0.49709(12) 0.67260(11) 0.61359(9) 0.0246(3) Uani 1 1 d . . . . .
N5 N 0.71931(11) 0.30068(10) 0.74549(8) 0.0296(3) Uani 1 1 d . . . . .
C5 C 0.59647(12) 0.53492(11) 0.66671(9) 0.0239(3) Uani 1 1 d . . . . .
F1 F 0.28874(8) 0.48478(7) 0.59702(7) 0.0414(3) Uani 1 1 d . . . . .
C1 C 0.30842(12) 0.69020(11) 0.54525(9) 0.0242(3) Uani 1 1 d . . . . .
O1 O 0.20557(11) 0.88513(10) 0.53536(9) 0.0495(4) Uani 1 1 d . . . . .
N1 N 0.39240(10) 0.62347(9) 0.57577(8) 0.0244(3) Uani 1 1 d . . . . .
C8 C 0.53313(12) 0.38320(11) 0.66124(9) 0.0238(3) Uani 1 1 d . . . . .
C7 C 0.65388(12) 0.38561(11) 0.70778(9) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.69667(12) 0.47921(11) 0.71125(9) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.18539(12) 0.66490(11) 0.50085(10) 0.0264(3) Uani 1 1 d . . . . .
C10 C 0.15468(15) 0.62102(15) 0.42571(12) 0.0436(5) Uani 1 1 d . . . . .
H10 H 0.211527 0.606797 0.402687 0.052 Uiso 1 1 calc R U . . .
C11 C 0.03965(15) 0.59755(17) 0.38354(13) 0.0537(6) Uani 1 1 d . . . . .
H11 H 0.019508 0.569571 0.331736 0.064 Uiso 1 1 calc R U . . .
C12 C -0.04365(15) 0.61514(15) 0.41739(14) 0.0499(5) Uani 1 1 d . . . . .
H12 H -0.120300 0.597015 0.389998 0.060 Uiso 1 1 calc R U . . .
C15 C 0.56610(13) 0.84996(11) 0.63681(9) 0.0264(3) Uani 1 1 d . . . . .
C14 C 0.10096(16) 0.68635(18) 0.53472(13) 0.0567(6) Uani 1 1 d . . . . .
H14 H 0.120500 0.717974 0.585002 0.068 Uiso 1 1 calc R U . . .
C13 C -0.01371(17) 0.6602(2) 0.49291(15) 0.0688(8) Uani 1 1 d . . . . .
H13 H -0.070792 0.673199 0.516012 0.083 Uiso 1 1 calc R U . . .
C16 C 0.53453(15) 0.93645(11) 0.66532(10) 0.0308(4) Uani 1 1 d . . . . .
H16 H 0.457062 0.947501 0.659612 0.037 Uiso 1 1 calc R U . . .
C17 C 0.61737(17) 1.00597(13) 0.70199(11) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.595599 1.062947 0.721488 0.048 Uiso 1 1 calc R U . . .
C18 C 0.73202(18) 0.99074(14) 0.70961(12) 0.0461(5) Uani 1 1 d . . . . .
H18 H 0.787626 1.037431 0.734335 0.055 Uiso 1 1 calc R U . . .
C19 C 0.76462(15) 0.90606(15) 0.68053(12) 0.0432(5) Uani 1 1 d . . . . .
H19 H 0.841997 0.896444 0.685266 0.052 Uiso 1 1 calc R U . . .
C20 C 0.68282(14) 0.83557(13) 0.64444(11) 0.0334(4) Uani 1 1 d . . . . .
H20 H 0.705374 0.778697 0.625287 0.040 Uiso 1 1 calc R U . . .
C21 C 0.81195(12) 0.52215(11) 0.75037(10) 0.0274(3) Uani 1 1 d . . . . .
C22 C 0.85085(13) 0.59396(13) 0.70940(12) 0.0350(4) Uani 1 1 d . . . . .
H22 H 0.805920 0.611098 0.656187 0.042 Uiso 1 1 calc R U . . .
C23 C 0.95648(15) 0.64022(14) 0.74755(14) 0.0473(5) Uani 1 1 d . . . . .
H23 H 0.982251 0.687860 0.719787 0.057 Uiso 1 1 calc R U . . .
C24 C 1.02265(16) 0.61536(17) 0.82634(15) 0.0556(6) Uani 1 1 d . . . . .
H24 H 1.092188 0.647563 0.852425 0.067 Uiso 1 1 calc R U . . .
C25 C 0.98648(16) 0.54307(17) 0.86679(13) 0.0509(5) Uani 1 1 d . . . . .
H25 H 1.032556 0.525766 0.919692 0.061 Uiso 1 1 calc R U . . .
C26 C 0.88194(14) 0.49581(13) 0.82934(11) 0.0365(4) Uani 1 1 d . . . . .
H26 H 0.858449 0.446525 0.856870 0.044 Uiso 1 1 calc R U . . .
C27 C 0.45624(13) 0.29813(11) 0.63609(9) 0.0248(3) Uani 1 1 d . . . . .
C28 C 0.48716(14) 0.22540(11) 0.59185(10) 0.0284(3) Uani 1 1 d . . . . .
H28 H 0.556219 0.230144 0.580519 0.034 Uiso 1 1 calc R U . . .
C29 C 0.41537(15) 0.14582(12) 0.56457(10) 0.0323(4) Uani 1 1 d . . . . .
H29 H 0.434907 0.098151 0.533553 0.039 Uiso 1 1 calc R U . . .
C30 C 0.31448(15) 0.13773(12) 0.58376(11) 0.0348(4) Uani 1 1 d . . . . .
H30 H 0.266340 0.084312 0.565633 0.042 Uiso 1 1 calc R U . . .
C31 C 0.28471(14) 0.20824(12) 0.62954(11) 0.0328(4) Uani 1 1 d . . . . .
H31 H 0.217703 0.201474 0.643262 0.039 Uiso 1 1 calc R U . . .
C32 C 0.35486(13) 0.28946(11) 0.65520(10) 0.0286(3) Uani 1 1 d . . . . .
H32 H 0.334003 0.337755 0.685025 0.034 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
B1 F1 1.362(2) . ?
B1 F2 1.373(2) . ?
B1 N1 1.569(2) . ?
B1 N3 1.580(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.414(2) . ?
C2 N4 1.443(2) . ?
O2 N4 1.2240(18) . ?
N2 C4 1.3185(18) . ?
N2 C5 1.322(2) . ?
O3 N5 1.2263(18) . ?
C3 C4 1.428(2) . ?
C3 C15 1.464(2) . ?
N3 C8 1.351(2) . ?
N3 C5 1.3973(19) . ?
N4 O1 1.2272(18) . ?
O4 N5 1.2234(18) . ?
C4 N1 1.4001(19) . ?
N5 C7 1.446(2) . ?
C5 C6 1.432(2) . ?
C1 N1 1.3478(19) . ?
C1 C9 1.481(2) . ?
C8 C7 1.423(2) . ?
C8 C27 1.476(2) . ?
C7 C6 1.389(2) . ?
C6 C21 1.467(2) . ?
C9 C10 1.367(2) . ?
C9 C14 1.378(3) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C15 C16 1.396(2) . ?
C15 C20 1.400(2) . ?
C14 C13 1.390(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.393(2) . ?
C21 C26 1.394(2) . ?
C22 C23 1.391(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.390(2) . ?
C27 C28 1.390(2) . ?
C28 C29 1.387(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.379(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.391(2) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 112.41(14) . . ?
F1 B1 N1 109.24(14) . . ?
F2 B1 N1 110.60(14) . . ?
F1 B1 N3 111.57(14) . . ?
F2 B1 N3 108.98(13) . . ?
N1 B1 N3 103.71(12) . . ?
C3 C2 C1 110.69(13) . . ?
C3 C2 N4 126.25(14) . . ?
C1 C2 N4 122.69(13) . . ?
C4 N2 C5 119.24(13) . . ?
C2 C3 C4 103.64(13) . . ?
C2 C3 C15 129.89(14) . . ?
C4 C3 C15 126.23(13) . . ?
C8 N3 C5 108.17(12) . . ?
C8 N3 B1 128.53(12) . . ?
C5 N3 B1 122.58(13) . . ?
O2 N4 O1 123.81(14) . . ?
O2 N4 C2 118.06(14) . . ?
O1 N4 C2 118.13(14) . . ?
N2 C4 N1 123.98(14) . . ?
N2 C4 C3 125.93(13) . . ?
N1 C4 C3 109.93(12) . . ?
O4 N5 O3 123.98(14) . . ?
O4 N5 C7 118.13(13) . . ?
O3 N5 C7 117.89(13) . . ?
N2 C5 N3 124.86(13) . . ?
N2 C5 C6 125.10(13) . . ?
N3 C5 C6 110.02(13) . . ?
N1 C1 C2 107.84(13) . . ?
N1 C1 C9 123.16(14) . . ?
C2 C1 C9 128.93(13) . . ?
C1 N1 C4 107.81(13) . . ?
C1 N1 B1 128.21(12) . . ?
C4 N1 B1 123.96(12) . . ?
N3 C8 C7 107.64(13) . . ?
N3 C8 C27 123.79(13) . . ?
C7 C8 C27 128.37(13) . . ?
C6 C7 C8 110.45(13) . . ?
C6 C7 N5 126.43(13) . . ?
C8 C7 N5 123.12(13) . . ?
C7 C6 C5 103.70(13) . . ?
C7 C6 C21 133.28(14) . . ?
C5 C6 C21 123.00(14) . . ?
C10 C9 C14 119.62(16) . . ?
C10 C9 C1 120.26(14) . . ?
C14 C9 C1 120.12(16) . . ?
C9 C10 C11 120.63(17) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.36(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.43(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C16 C15 C20 118.78(15) . . ?
C16 C15 C3 120.24(14) . . ?
C20 C15 C3 120.94(15) . . ?
C9 C14 C13 119.3(2) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C17 C16 C15 120.68(17) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.01(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.10(17) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 120.46(18) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 119.96(18) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C22 C21 C26 118.90(15) . . ?
C22 C21 C6 119.49(14) . . ?
C26 C21 C6 121.56(15) . . ?
C23 C22 C21 120.44(18) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.28(18) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.51(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 119.99(18) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C32 C27 C28 119.81(14) . . ?
C32 C27 C8 121.85(14) . . ?
C28 C27 C8 118.34(14) . . ?
C29 C28 C27 120.22(15) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 119.62(15) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 120.55(15) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.03(16) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 119.72(15) . . ?
C27 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.051


_exptl_crystal_preparation       Luminescent
