# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_pr_rb1_auto
_database_code_depnum_ccdc_archive 'CCDC 2300176'
loop_
_audit_author_name
_audit_author_address
'Miguel Chacon Teran'
;The University of California, Merced
United States of America
;
_audit_update_record             
;
2023-10-09 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_date             2023-10-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        'Benzoyl Pyrazinium'
_chemical_formula_moiety         'C12 H11 N2 O, B F3.954'
_chemical_formula_sum            'C12 H11 B F3.95 N2 O'
_chemical_formula_weight         285.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H11 N2 O1 B1 F4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4674(5)
_cell_length_b                   22.5949(16)
_cell_length_c                   7.9393(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.116(6)
_cell_angle_gamma                90
_cell_volume                     1331.94(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3207
_cell_measurement_temperature    298.76(10)
_cell_measurement_theta_max      30.5980
_cell_measurement_theta_min      2.7360
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
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_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             582
_exptl_crystal_preparation       'Slow crysatliazation'
_exptl_crystal_recrystallization_method 'Crystalized in ACN'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.692
_diffrn_reflns_theta_min         2.733
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.76(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  26.00   0.50   15.00    --   -5.19 -99.00  90.00   52
  2  ω    -54.00   8.00   0.50   15.00    --   -5.19 -38.00 -60.00  124
  3  ω    -70.00  -4.00   0.50   15.00    --    5.35 -19.00  60.00  132
  4  ω     -7.00  58.00   0.50   15.00    --    5.35  38.00-150.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0506760000
_diffrn_orient_matrix_UB_12      -0.0002930000
_diffrn_orient_matrix_UB_13      -0.0706689000
_diffrn_orient_matrix_UB_21      0.0015797000
_diffrn_orient_matrix_UB_22      -0.0313810000
_diffrn_orient_matrix_UB_23      0.0020820000
_diffrn_orient_matrix_UB_31      -0.0809558000
_diffrn_orient_matrix_UB_32      -0.0008185000
_diffrn_orient_matrix_UB_33      -0.0554560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             3437
_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 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.630
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.1261
_refine_ls_restrained_S_all      1.630
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4146
_refine_ls_wR_factor_ref         0.4453
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H),
 C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00F(H00B,H00F,H00G)
;
_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
N001 N 0.9135(4) 0.30692(14) 0.4855(3) 0.0604(9) Uani 1 1 d . . . . .
O002 O 0.4583(3) 0.39091(15) 0.6039(5) 0.0964(12) Uani 1 1 d . . . . .
N003 N 0.8981(4) 0.42628(14) 0.5367(4) 0.0681(9) Uani 1 1 d . . . . .
C004 C 0.7630(4) 0.39140(16) 0.5679(4) 0.0549(9) Uani 1 1 d . . . . .
C005 C 0.7646(4) 0.33150(16) 0.5402(4) 0.0543(9) Uani 1 1 d . . . . .
H005 H 0.665796 0.308268 0.558656 0.065 Uiso 1 1 calc R U . . .
F006 F 0.8752(6) 0.25784(17) -0.1155(5) 0.1336(14) Uani 1 1 d . . . . .
C007 C 0.5980(4) 0.41754(17) 0.6336(5) 0.0622(9) Uani 1 1 d . . . . .
F008 F 1.0362(5) 0.3384(2) -0.1364(5) 0.1459(17) Uani 1 1 d . . . . .
C009 C 0.6084(6) 0.47410(17) 0.7262(5) 0.0704(11) Uani 1 1 d . . . . .
C00A C 1.0514(4) 0.33991(19) 0.4561(5) 0.0657(10) Uani 1 1 d . . . . .
H00A H 1.154285 0.322870 0.420478 0.079 Uiso 1 1 calc R U . . .
F00B F 1.0412(7) 0.2951(3) 0.1062(5) 0.169(2) Uani 1 1 d . . . . .
C00C C 1.0412(5) 0.4001(2) 0.4788(6) 0.0739(11) Uani 1 1 d . . . . .
H00C H 1.136988 0.423620 0.453285 0.089 Uiso 1 1 calc R U . . .
C00D C 0.4506(7) 0.5052(2) 0.7372(6) 0.0867(14) Uani 1 1 d . . . . .
H00D H 0.342835 0.491333 0.681436 0.104 Uiso 1 1 calc R U . . .
C00E C 0.7701(8) 0.4956(2) 0.8097(7) 0.0887(14) Uani 1 1 d . . . . .
H00E H 0.876240 0.474686 0.802210 0.106 Uiso 1 1 calc R U . . .
C00F C 0.9217(7) 0.2426(2) 0.4634(8) 0.0939(15) Uani 1 1 d . . . . .
H00B H 0.844839 0.223690 0.536709 0.141 Uiso 1 1 calc R U . . .
H00F H 1.043320 0.229288 0.491172 0.141 Uiso 1 1 calc R U . . .
H00G H 0.882183 0.232671 0.347795 0.141 Uiso 1 1 calc R U . . .
F00G F 0.7841(8) 0.3403(3) -0.0218(13) 0.229(5) Uani 0.954(18) 1 d . . . A 1
C00H C 0.4527(11) 0.5577(3) 0.8324(7) 0.122(3) Uani 1 1 d . . . . .
H00H H 0.346339 0.578335 0.841406 0.147 Uiso 1 1 calc R U . . .
B00I B 0.9246(7) 0.3076(2) -0.0291(6) 0.0748(13) Uani 1 1 d . . . . .
C00J C 0.6111(16) 0.5781(3) 0.9113(8) 0.139(3) Uani 1 1 d . . . . .
H00J H 0.612588 0.613219 0.972494 0.166 Uiso 1 1 calc R U . . .
C00K C 0.7750(12) 0.5466(3) 0.9018(9) 0.129(2) Uani 1 1 d . . . . .
H00K H 0.882778 0.560541 0.957130 0.155 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
N001 C005 1.355(4) . ?
N001 C00A 1.312(5) . ?
N001 C00F 1.466(5) . ?
O002 C007 1.205(4) . ?
N003 C004 1.324(4) . ?
N003 C00C 1.344(5) . ?
C004 C005 1.371(5) . ?
C004 C007 1.509(5) . ?
C005 H005 0.9300 . ?
F006 B00I 1.347(6) . ?
C007 C009 1.472(6) . ?
F008 B00I 1.434(7) . ?
C009 C00D 1.383(6) . ?
C009 C00E 1.402(7) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.376(6) . ?
F00B B00I 1.339(6) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00H 1.407(8) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.363(8) . ?
C00F H00B 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
F00G B00I 1.291(7) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.359(11) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.424(12) . ?
C00K H00K 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
C005 N001 C00F 119.4(3) . . ?
C00A N001 C005 120.7(3) . . ?
C00A N001 C00F 119.9(3) . . ?
C004 N003 C00C 116.9(3) . . ?
N003 C004 C005 122.5(3) . . ?
N003 C004 C007 119.9(3) . . ?
C005 C004 C007 117.6(3) . . ?
N001 C005 C004 118.5(3) . . ?
N001 C005 H005 120.7 . . ?
C004 C005 H005 120.7 . . ?
O002 C007 C004 117.3(3) . . ?
O002 C007 C009 122.0(3) . . ?
C009 C007 C004 120.7(3) . . ?
C00D C009 C007 118.2(4) . . ?
C00D C009 C00E 119.4(4) . . ?
C00E C009 C007 122.3(4) . . ?
N001 C00A H00A 120.5 . . ?
N001 C00A C00C 118.9(3) . . ?
C00C C00A H00A 120.5 . . ?
N003 C00C C00A 122.4(3) . . ?
N003 C00C H00C 118.8 . . ?
C00A C00C H00C 118.8 . . ?
C009 C00D H00D 119.9 . . ?
C009 C00D C00H 120.1(6) . . ?
C00H C00D H00D 119.9 . . ?
C009 C00E H00E 119.4 . . ?
C00K C00E C009 121.3(6) . . ?
C00K C00E H00E 119.4 . . ?
N001 C00F H00B 109.5 . . ?
N001 C00F H00F 109.5 . . ?
N001 C00F H00G 109.5 . . ?
H00B C00F H00F 109.5 . . ?
H00B C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
C00D C00H H00H 120.2 . . ?
C00J C00H C00D 119.6(6) . . ?
C00J C00H H00H 120.2 . . ?
F006 B00I F008 104.4(4) . . ?
F00B B00I F006 110.6(5) . . ?
F00B B00I F008 102.1(4) . . ?
F00G B00I F006 108.7(5) . . ?
F00G B00I F008 105.9(6) . . ?
F00G B00I F00B 123.2(6) . . ?
C00H C00J H00J 119.4 . . ?
C00H C00J C00K 121.1(6) . . ?
C00K C00J H00J 119.4 . . ?
C00E C00K C00J 118.5(7) . . ?
C00E C00K H00K 120.8 . . ?
C00J C00K H00K 120.8 . . ?

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
N001 C00A C00C N003 2.7(6) . . . . ?
O002 C007 C009 C00D -18.3(6) . . . . ?
O002 C007 C009 C00E 158.4(4) . . . . ?
N003 C004 C005 N001 2.8(5) . . . . ?
N003 C004 C007 O002 154.0(4) . . . . ?
N003 C004 C007 C009 -24.4(5) . . . . ?
C004 N003 C00C C00A -1.5(6) . . . . ?
C004 C007 C009 C00D 160.1(4) . . . . ?
C004 C007 C009 C00E -23.2(6) . . . . ?
C005 N001 C00A C00C -1.2(5) . . . . ?
C005 C004 C007 O002 -25.0(5) . . . . ?
C005 C004 C007 C009 156.6(3) . . . . ?
C007 C004 C005 N001 -178.3(3) . . . . ?
C007 C009 C00D C00H 176.4(4) . . . . ?
C007 C009 C00E C00K -176.7(5) . . . . ?
C009 C00D C00H C00J 1.0(8) . . . . ?
C009 C00E C00K C00J -0.2(9) . . . . ?
C00A N001 C005 C004 -1.4(5) . . . . ?
C00C N003 C004 C005 -1.3(5) . . . . ?
C00C N003 C004 C007 179.8(3) . . . . ?
C00D C009 C00E C00K 0.0(7) . . . . ?
C00D C00H C00J C00K -1.2(10) . . . . ?
C00E C009 C00D C00H -0.4(7) . . . . ?
C00F N001 C005 C004 176.9(3) . . . . ?
C00F N001 C00A C00C -179.5(4) . . . . ?
C00H C00J C00K C00E 0.8(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'Nylon loop'
_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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.714
