# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_13
_database_code_depnum_ccdc_archive 'CCDC 2209647'
loop_
_audit_author_name
_audit_author_address
'Alexandra M. Z. Slawin'
;university of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-09-26
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C17 H16 B Br F4 N4 O'
_chemical_formula_moiety         'C17 H16 B Br F4 N4 O'
_chemical_formula_weight         459.05
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.7229(6)
_cell_length_b                   11.8712(8)
_cell_length_c                   15.4592(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1784.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2359
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920.00
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.931

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            18551
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4098
_reflns_number_gt                3220
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0587
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4098
_refine_ls_number_parameters     257
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br17 Br 0.50498(5) 0.48412(3) 0.09377(2) 0.03326(11) Uani 1 1 d . . . . .
F1 F 0.0843(4) 0.4614(3) 0.3672(2) 0.0744(10) Uani 1 1 d . . . . .
F2 F -0.0353(3) 0.6183(2) 0.3832(2) 0.0621(8) Uani 1 1 d . . . . .
F3 F -0.1431(3) 0.4634(3) 0.3349(2) 0.0741(10) Uani 1 1 d . . . . .
F4 F 0.0096(3) 0.5525(3) 0.24954(16) 0.0706(9) Uani 1 1 d . . . . .
O15 O 0.2668(3) 0.6145(2) 0.20717(16) 0.0286(6) Uani 1 1 d D . . . .
N1 N 0.3513(3) 0.5724(2) 0.43327(17) 0.0183(6) Uani 1 1 d . . . . .
N2 N 0.2963(3) 0.6347(3) 0.5006(2) 0.0223(7) Uani 1 1 d . . . . .
N7 N 0.2559(3) 0.7137(2) 0.37365(18) 0.0204(7) Uani 1 1 d . . . . .
N21 N 0.5537(3) 0.7081(3) 0.2959(2) 0.0263(7) Uani 1 1 d . . . . .
C3 C 0.2399(4) 0.7198(3) 0.4609(2) 0.0221(8) Uani 1 1 d . . . . .
C4 C 0.1643(4) 0.8236(3) 0.4863(3) 0.0310(10) Uani 1 1 d . . . . .
H4A H 0.226202 0.878785 0.514377 0.037 Uiso 1 1 calc R U . . .
H4B H 0.087101 0.806115 0.525795 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1116(4) 0.8678(3) 0.3983(3) 0.0335(9) Uani 1 1 d . . . . .
H5A H 0.012280 0.851439 0.392017 0.040 Uiso 1 1 calc R U . . .
H5B H 0.124845 0.950383 0.394675 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1934(4) 0.8087(3) 0.3261(3) 0.0298(9) Uani 1 1 d . . . . .
H6A H 0.132198 0.781850 0.279228 0.036 Uiso 1 1 calc R U . . .
H6B H 0.264497 0.858940 0.301280 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3272(3) 0.6201(3) 0.3564(2) 0.0184(7) Uani 1 1 d . . . . .
C9 C 0.4199(3) 0.4685(3) 0.4529(2) 0.0191(7) Uani 1 1 d . . . . .
C10 C 0.3699(4) 0.4036(3) 0.5202(2) 0.0230(8) Uani 1 1 d . . . . .
H10 H 0.290463 0.426342 0.551384 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4380(4) 0.3048(3) 0.5411(3) 0.0263(8) Uani 1 1 d . . . . .
H11 H 0.406247 0.260375 0.588161 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5517(4) 0.2700(3) 0.4944(3) 0.0259(8) Uani 1 1 d . . . . .
H12 H 0.596554 0.201416 0.508582 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5997(4) 0.3359(3) 0.4268(2) 0.0273(9) Uani 1 1 d . . . . .
H13 H 0.676889 0.311497 0.394076 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5363(3) 0.4365(3) 0.4066(3) 0.0231(8) Uani 1 1 d . . . . .
H14 H 0.571497 0.483125 0.361867 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3662(4) 0.5789(3) 0.2680(2) 0.0212(8) Uani 1 1 d . . . . .
H15 H 0.372607 0.494794 0.267995 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5043(4) 0.6297(2) 0.24239(19) 0.0211(6) Uani 1 1 d . . . . .
C17 C 0.5733(4) 0.5974(3) 0.1677(2) 0.0242(8) Uani 1 1 d . . . . .
C18 C 0.6964(4) 0.6503(3) 0.1473(3) 0.0309(9) Uani 1 1 d . . . . .
H18 H 0.744915 0.630887 0.096122 0.037 Uiso 1 1 calc R U . . .
C19 C 0.7467(4) 0.7310(3) 0.2021(3) 0.0338(10) Uani 1 1 d . . . . .
H19 H 0.830393 0.768782 0.189317 0.041 Uiso 1 1 calc R U . . .
C20 C 0.6744(4) 0.7563(3) 0.2757(3) 0.0311(9) Uani 1 1 d . . . . .
H20 H 0.711455 0.810611 0.314335 0.037 Uiso 1 1 calc R U . . .
B1 B -0.0240(5) 0.5219(4) 0.3339(3) 0.0358(11) Uani 1 1 d . . . . .
H15O H 0.179(2) 0.581(3) 0.223(3) 0.051(14) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br17 C17 1.885(4) . ?
F1 B1 1.374(6) . ?
F2 B1 1.379(5) . ?
F3 B1 1.350(5) . ?
F4 B1 1.393(5) . ?
O15 C15 1.413(4) . ?
O15 H15O 0.974(7) . ?
N1 C8 1.337(4) . ?
N1 N2 1.384(4) . ?
N1 C9 1.435(4) . ?
N2 C3 1.302(5) . ?
N7 C8 1.337(4) . ?
N7 C3 1.360(4) . ?
N7 C6 1.477(5) . ?
N21 C16 1.334(4) . ?
N21 C20 1.342(5) . ?
C3 C4 1.488(5) . ?
C4 C5 1.545(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.541(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C15 1.501(5) . ?
C9 C10 1.382(5) . ?
C9 C14 1.392(5) . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.524(5) . ?
C15 H15 1.0000 . ?
C16 C17 1.390(5) . ?
C17 C18 1.388(5) . ?
C18 C19 1.369(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(6) . ?
C19 H19 0.9500 . ?
C20 H20 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
C15 O15 H15O 108(3) . . ?
C8 N1 N2 112.0(3) . . ?
C8 N1 C9 129.3(3) . . ?
N2 N1 C9 118.7(3) . . ?
C3 N2 N1 102.9(3) . . ?
C8 N7 C3 107.5(3) . . ?
C8 N7 C6 138.5(3) . . ?
C3 N7 C6 114.0(3) . . ?
C16 N21 C20 117.9(3) . . ?
N2 C3 N7 112.2(3) . . ?
N2 C3 C4 136.6(3) . . ?
N7 C3 C4 111.2(3) . . ?
C3 C4 C5 102.3(3) . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
C5 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C6 C5 C4 108.2(3) . . ?
C6 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N7 C6 C5 101.5(3) . . ?
N7 C6 H6A 111.5 . . ?
C5 C6 H6A 111.5 . . ?
N7 C6 H6B 111.5 . . ?
C5 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
N7 C8 N1 105.4(3) . . ?
N7 C8 C15 125.7(3) . . ?
N1 C8 C15 128.8(3) . . ?
C10 C9 C14 121.3(3) . . ?
C10 C9 N1 118.4(3) . . ?
C14 C9 N1 120.3(3) . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 118.9(3) . . ?
C13 C14 H14 120.5 . . ?
C9 C14 H14 120.5 . . ?
O15 C15 C8 109.6(3) . . ?
O15 C15 C16 108.1(3) . . ?
C8 C15 C16 109.3(3) . . ?
O15 C15 H15 109.9 . . ?
C8 C15 H15 109.9 . . ?
C16 C15 H15 109.9 . . ?
N21 C16 C17 122.3(4) . . ?
N21 C16 C15 115.6(3) . . ?
C17 C16 C15 122.1(3) . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 Br17 119.3(3) . . ?
C16 C17 Br17 122.1(3) . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N21 C20 C19 123.2(4) . . ?
N21 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
F3 B1 F1 112.6(4) . . ?
F3 B1 F2 110.6(4) . . ?
F1 B1 F2 106.7(4) . . ?
F3 B1 F4 110.2(4) . . ?
F1 B1 F4 107.9(4) . . ?
F2 B1 F4 108.6(4) . . ?

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
C8 N1 N2 C3 -0.1(4) . . . . ?
C9 N1 N2 C3 -178.3(3) . . . . ?
N1 N2 C3 N7 0.3(4) . . . . ?
N1 N2 C3 C4 -178.3(4) . . . . ?
C8 N7 C3 N2 -0.4(4) . . . . ?
C6 N7 C3 N2 -180.0(3) . . . . ?
C8 N7 C3 C4 178.5(3) . . . . ?
C6 N7 C3 C4 -1.0(5) . . . . ?
N2 C3 C4 C5 -170.5(4) . . . . ?
N7 C3 C4 C5 10.9(4) . . . . ?
C3 C4 C5 C6 -16.4(4) . . . . ?
C8 N7 C6 C5 171.3(4) . . . . ?
C3 N7 C6 C5 -9.4(4) . . . . ?
C4 C5 C6 N7 15.7(4) . . . . ?
C3 N7 C8 N1 0.4(4) . . . . ?
C6 N7 C8 N1 179.7(4) . . . . ?
C3 N7 C8 C15 178.8(3) . . . . ?
C6 N7 C8 C15 -1.9(7) . . . . ?
N2 N1 C8 N7 -0.2(4) . . . . ?
C9 N1 C8 N7 177.8(3) . . . . ?
N2 N1 C8 C15 -178.6(3) . . . . ?
C9 N1 C8 C15 -0.5(6) . . . . ?
C8 N1 C9 C10 -142.8(4) . . . . ?
N2 N1 C9 C10 35.2(4) . . . . ?
C8 N1 C9 C14 39.1(5) . . . . ?
N2 N1 C9 C14 -142.9(3) . . . . ?
C14 C9 C10 C11 -0.1(5) . . . . ?
N1 C9 C10 C11 -178.2(3) . . . . ?
C9 C10 C11 C12 -1.6(5) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 C9 -2.7(5) . . . . ?
C10 C9 C14 C13 2.2(5) . . . . ?
N1 C9 C14 C13 -179.8(3) . . . . ?
N7 C8 C15 O15 -29.3(5) . . . . ?
N1 C8 C15 O15 148.7(3) . . . . ?
N7 C8 C15 C16 89.0(4) . . . . ?
N1 C8 C15 C16 -92.9(4) . . . . ?
C20 N21 C16 C17 0.0(5) . . . . ?
C20 N21 C16 C15 -179.3(3) . . . . ?
O15 C15 C16 N21 111.6(3) . . . . ?
C8 C15 C16 N21 -7.6(4) . . . . ?
O15 C15 C16 C17 -67.7(4) . . . . ?
C8 C15 C16 C17 173.0(3) . . . . ?
N21 C16 C17 C18 -1.4(5) . . . . ?
C15 C16 C17 C18 177.9(3) . . . . ?
N21 C16 C17 Br17 178.5(3) . . . . ?
C15 C16 C17 Br17 -2.2(5) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
Br17 C17 C18 C19 -178.8(3) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C16 N21 C20 C19 1.8(6) . . . . ?
C18 C19 C20 N21 -2.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O15 H15o F4 . . . 2.688(4) 0.97(3) 1.73(3) 167(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
