# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2333148'
loop_
_audit_author_name
_audit_author_address
'Regine Herbst-Irmer'
;University of Goettingen
Germany
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 B N2 O2'
_chemical_formula_sum            'C17 H15 B N2 O2'
_chemical_formula_weight         290.12

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.336(3)
_cell_length_b                   6.707(2)
_cell_length_c                   13.506(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1389.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9498
_cell_measurement_theta_min      3.0165
_cell_measurement_theta_max      27.1275

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.708
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.163
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microsource'
_diffrn_detector_type            'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38676
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.009
_diffrn_reflns_theta_max         27.126
_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
_reflns_number_total             1678
_reflns_number_gt                1577
_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 APEX2 v2012.2'
_computing_cell_refinement       'Bruker SAINT V8.40A'
_computing_data_reduction        'Bruker SAINT V8.40A'
_computing_structure_solution    'SHELXT(Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0581P)²+0.4876P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1678
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O1 O 0.08775(6) 0.750000 0.65029(7) 0.0181(2) Uani 1 2 d S T P . .
O2 O 0.18336(6) 0.750000 0.31316(7) 0.0188(2) Uani 1 2 d S T P . .
N1 N 0.23005(7) 0.750000 0.61373(8) 0.0154(3) Uani 1 2 d S T P . .
N2 N 0.28016(7) 0.750000 0.43746(8) 0.0154(2) Uani 1 2 d S T P . .
C1 C 0.22270(9) 0.750000 0.71756(10) 0.0152(3) Uani 1 2 d S T P . .
C2 C 0.28431(9) 0.750000 0.79419(10) 0.0166(3) Uani 1 2 d S T P . .
C3 C 0.24955(9) 0.750000 0.88998(10) 0.0185(3) Uani 1 2 d S T P . .
H3 H 0.288743 0.750000 0.944447 0.022 Uiso 1 2 calc R U P . .
C4 C 0.16000(9) 0.750000 0.90954(10) 0.0186(3) Uani 1 2 d S T P . .
H4 H 0.140282 0.750000 0.976225 0.022 Uiso 1 2 calc R U P . .
C5 C 0.09927(9) 0.750000 0.83294(10) 0.0177(3) Uani 1 2 d S T P . .
H5 H 0.038205 0.750000 0.844740 0.021 Uiso 1 2 calc R U P . .
C6 C 0.13392(9) 0.750000 0.73874(10) 0.0161(3) Uani 1 2 d S T P . .
C7 C 0.14880(8) 0.750000 0.57779(10) 0.0167(3) Uani 1 2 d S T P . .
C8 C 0.12567(9) 0.750000 0.47841(10) 0.0199(3) Uani 1 2 d S T P . .
H8 H 0.066712 0.750000 0.456842 0.024 Uiso 1 2 calc R U P . .
C9 C 0.19562(9) 0.750000 0.41295(10) 0.0168(3) Uani 1 2 d S T P . .
C10 C 0.26646(9) 0.750000 0.27224(10) 0.0168(3) Uani 1 2 d S T P . .
C11 C 0.28612(10) 0.750000 0.17263(10) 0.0200(3) Uani 1 2 d S T P . .
H11 H 0.242450 0.750000 0.122743 0.024 Uiso 1 2 calc R U P . .
C12 C 0.37523(10) 0.750000 0.15057(10) 0.0206(3) Uani 1 2 d S T P . .
H12 H 0.393499 0.750000 0.083360 0.025 Uiso 1 2 calc R U P . .
C13 C 0.43785(9) 0.750000 0.22577(10) 0.0193(3) Uani 1 2 d S T P . .
H13 H 0.497677 0.750000 0.207545 0.023 Uiso 1 2 calc R U P . .
C14 C 0.41673(9) 0.750000 0.32667(10) 0.0166(3) Uani 1 2 d S T P . .
C15 C 0.32755(9) 0.750000 0.34832(9) 0.0157(3) Uani 1 2 d S T P . .
C16 C 0.38154(9) 0.750000 0.77824(10) 0.0225(3) Uani 1 2 d S T P . .
H16A H 0.410965 0.715701 0.840359 0.034 Uiso 0.5 1 calc R U P . .
H16B H 0.400309 0.882696 0.756594 0.034 Uiso 0.5 1 calc R U P . .
H16C H 0.396594 0.651603 0.727396 0.034 Uiso 0.5 1 calc R U P . .
C17 C 0.48784(9) 0.750000 0.40352(11) 0.0208(3) Uani 1 2 d S T P . .
H17A H 0.470917 0.836385 0.458798 0.031 Uiso 0.5 1 calc R U P . .
H17B H 0.542002 0.799740 0.373984 0.031 Uiso 0.5 1 calc R U P . .
H17C H 0.496891 0.613875 0.427807 0.031 Uiso 0.5 1 calc R U P . .
B1 B 0.31491(9) 0.750000 0.54778(11) 0.0172(3) Uani 1 2 d S T P . .
H1 H 0.3542(8) 0.8877(19) 0.5617(9) 0.024(3) Uiso 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
O1 C7 1.3548(16) . ?
O1 C6 1.3887(15) . ?
O2 C9 1.3609(16) . ?
O2 C10 1.3892(16) . ?
N1 C7 1.3373(17) . ?
N1 C1 1.4069(16) . ?
N1 B1 1.5770(18) . ?
N2 C9 1.3381(17) . ?
N2 C15 1.4062(16) . ?
N2 B1 1.5824(18) . ?
C1 C6 1.3912(18) . ?
C1 C2 1.4014(18) . ?
C2 C3 1.3992(18) . ?
C2 C16 1.5066(18) . ?
C3 C4 1.3986(19) . ?
C4 C5 1.3921(19) . ?
C5 C6 1.3788(18) . ?
C7 C8 1.3883(18) . ?
C8 C9 1.3901(19) . ?
C10 C11 1.3788(18) . ?
C10 C15 1.3905(18) . ?
C11 C12 1.399(2) . ?
C12 C13 1.3977(19) . ?
C13 C14 1.4008(18) . ?
C14 C15 1.3985(19) . ?
C14 C17 1.5055(19) . ?
B1 H1 1.118(13) . ?
B1 H1 1.118(13) 7_575 ?

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
C7 O1 C6 105.63(10) . . ?
C9 O2 C10 105.50(10) . . ?
C7 N1 C1 106.69(11) . . ?
C7 N1 B1 124.33(11) . . ?
C1 N1 B1 128.98(11) . . ?
C9 N2 C15 106.80(11) . . ?
C9 N2 B1 124.00(11) . . ?
C15 N2 B1 129.20(10) . . ?
C6 C1 C2 120.53(12) . . ?
C6 C1 N1 106.46(11) . . ?
C2 C1 N1 133.01(12) . . ?
C3 C2 C1 115.21(12) . . ?
C3 C2 C16 120.61(12) . . ?
C1 C2 C16 124.18(13) . . ?
C4 C3 C2 123.29(13) . . ?
C5 C4 C3 121.10(13) . . ?
C6 C5 C4 115.34(12) . . ?
C5 C6 O1 126.68(12) . . ?
C5 C6 C1 124.53(12) . . ?
O1 C6 C1 108.79(11) . . ?
N1 C7 O1 112.43(11) . . ?
N1 C7 C8 126.09(12) . . ?
O1 C7 C8 121.48(12) . . ?
C7 C8 C9 114.69(12) . . ?
N2 C9 O2 112.27(12) . . ?
N2 C9 C8 126.19(12) . . ?
O2 C9 C8 121.54(12) . . ?
C11 C10 O2 126.08(12) . . ?
C11 C10 C15 125.01(13) . . ?
O2 C10 C15 108.91(11) . . ?
C10 C11 C12 114.93(13) . . ?
C13 C12 C11 121.10(13) . . ?
C12 C13 C14 123.24(13) . . ?
C15 C14 C13 115.44(12) . . ?
C15 C14 C17 124.35(12) . . ?
C13 C14 C17 120.21(13) . . ?
C10 C15 C14 120.29(12) . . ?
C10 C15 N2 106.53(11) . . ?
C14 C15 N2 133.18(12) . . ?
H1 B1 H1 111.3(12) . 7_575 ?
H1 B1 N1 110.5(6) . . ?
H1 B1 N1 110.5(6) 7_575 . ?
H1 B1 N2 109.9(6) . . ?
H1 B1 N2 109.9(6) 7_575 . ?
N1 B1 N2 104.71(10) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2333150'
loop_
_audit_author_name
_audit_author_address
'Regine Herbst-Irmer'
;University of Goettingen
Germany
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 B Cl2 N2 O2'
_chemical_formula_sum            'C17 H13 B Cl2 N2 O2'
_chemical_formula_weight         359.00

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.935(2)
_cell_length_b                   6.703(2)
_cell_length_c                   14.407(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.76(2)
_cell_angle_gamma                90
_cell_volume                     763.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.5755
_cell_measurement_theta_max      27.12

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.437
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker Rotating Anode'
_diffrn_detector_type            'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'Bruker Smart APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17901
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.576
_diffrn_reflns_theta_max         27.144
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1843
_reflns_number_gt                1754
_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 APEX2 v2012.2'
_computing_cell_refinement       'Bruker SAINT V8.40A'
_computing_data_reduction        'Bruker SAINT V8.40A'
_computing_structure_solution    'SHELXT(Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0386P)²+0.4777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1843
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.4122(2) 0.750000 0.92282(11) 0.0128(3) Uani 1 2 d S T P . .
C2 C 0.2731(2) 0.750000 0.97712(11) 0.0149(3) Uani 1 2 d S T P . .
C3 C 0.3149(2) 0.750000 1.07410(12) 0.0167(3) Uani 1 2 d S T P . .
H3 H 0.225172 0.750000 1.113832 0.020 Uiso 1 2 calc R U P . .
C4 C 0.4801(2) 0.750000 1.11509(12) 0.0176(3) Uani 1 2 d S T P . .
H4 H 0.499529 0.750000 1.181048 0.021 Uiso 1 2 calc R U P . .
C5 C 0.6168(2) 0.750000 1.06074(11) 0.0161(3) Uani 1 2 d S T P . .
H5 H 0.730708 0.750000 1.086974 0.019 Uiso 1 2 calc R U P . .
C6 C 0.5752(2) 0.750000 0.96638(11) 0.0137(3) Uani 1 2 d S T P . .
C7 C 0.6017(2) 0.750000 0.81693(11) 0.0135(3) Uani 1 2 d S T P . .
C8 C 0.6803(2) 0.750000 0.73522(11) 0.0152(3) Uani 1 2 d S T P . .
H8 H 0.799855 0.750000 0.734048 0.018 Uiso 1 2 calc R U P . .
C9 C 0.5718(2) 0.750000 0.65510(11) 0.0138(3) Uani 1 2 d S T P . .
C10 C 0.4894(2) 0.750000 0.50678(11) 0.0134(3) Uani 1 2 d S T P . .
C11 C 0.4944(2) 0.750000 0.41142(12) 0.0160(3) Uani 1 2 d S T P . .
H11 H 0.597236 0.750000 0.382067 0.019 Uiso 1 2 calc R U P . .
C12 C 0.3368(2) 0.750000 0.36167(12) 0.0170(3) Uani 1 2 d S T P . .
H12 H 0.330033 0.750000 0.295524 0.020 Uiso 1 2 calc R U P . .
C13 C 0.1887(2) 0.750000 0.40689(11) 0.0152(3) Uani 1 2 d S T P . .
H13 H 0.084068 0.750000 0.369732 0.018 Uiso 1 2 calc R U P . .
C14 C 0.1843(2) 0.750000 0.50413(11) 0.0128(3) Uani 1 2 d S T P . .
C15 C 0.3434(2) 0.750000 0.55445(11) 0.0123(3) Uani 1 2 d S T P . .
C16 C 0.0139(2) 0.750000 0.54274(12) 0.0154(3) Uani 1 2 d S T P . .
H16A H 0.010954 0.645891 0.590335 0.023 Uiso 0.5 1 calc R U P . .
H16B H -0.074066 0.723816 0.492392 0.023 Uiso 0.5 1 calc R U P . .
H16C H -0.006132 0.880293 0.570652 0.023 Uiso 0.5 1 calc R U P . .
C17 C 0.0891(2) 0.750000 0.94238(12) 0.0203(4) Uani 1 2 d S T P . .
H17A H 0.069482 0.849730 0.892924 0.030 Uiso 0.5 1 calc R U P . .
H17B H 0.020473 0.782541 0.993825 0.030 Uiso 0.5 1 calc R U P . .
H17C H 0.057425 0.617729 0.917747 0.030 Uiso 0.5 1 calc R U P . .
B1 B 0.3040(2) 0.750000 0.73933(12) 0.0120(3) Uani 1 2 d S T P . .
N1 N 0.43360(17) 0.750000 0.82522(9) 0.0121(3) Uani 1 2 d S T P . .
N2 N 0.40142(17) 0.750000 0.65106(9) 0.0119(3) Uani 1 2 d S T P . .
O1 O 0.69203(15) 0.750000 0.90017(8) 0.0147(3) Uani 1 2 d S T P . .
O2 O 0.63030(15) 0.750000 0.57029(8) 0.0152(3) Uani 1 2 d S T P . .
Cl1 Cl 0.17154(3) 0.51953(4) 0.74036(2) 0.01692(11) 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
C1 C6 1.390(2) . ?
C1 C2 1.405(2) . ?
C1 N1 1.430(2) . ?
C2 C3 1.409(2) . ?
C2 C17 1.503(2) . ?
C3 C4 1.392(3) . ?
C4 C5 1.390(2) . ?
C5 C6 1.372(2) . ?
C6 O1 1.384(2) . ?
C7 O1 1.345(2) . ?
C7 N1 1.349(2) . ?
C7 C8 1.377(2) . ?
C8 C9 1.382(2) . ?
C9 O2 1.342(2) . ?
C9 N2 1.349(2) . ?
C10 C11 1.378(2) . ?
C10 O2 1.385(2) . ?
C10 C15 1.396(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.404(2) . ?
C14 C15 1.402(2) . ?
C14 C16 1.504(2) . ?
C15 N2 1.429(2) . ?
B1 N1 1.542(2) . ?
B1 N2 1.542(2) . ?
B1 Cl1 1.8692(11) 4_575 ?
B1 Cl1 1.8692(11) . ?

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 C1 C2 119.55(15) . . ?
C6 C1 N1 105.21(14) . . ?
C2 C1 N1 135.24(15) . . ?
C1 C2 C3 114.87(15) . . ?
C1 C2 C17 126.93(15) . . ?
C3 C2 C17 118.20(15) . . ?
C4 C3 C2 123.84(16) . . ?
C5 C4 C3 120.84(16) . . ?
C6 C5 C4 115.02(16) . . ?
C5 C6 O1 124.24(15) . . ?
C5 C6 C1 125.88(16) . . ?
O1 C6 C1 109.88(14) . . ?
O1 C7 N1 112.25(14) . . ?
O1 C7 C8 121.08(15) . . ?
N1 C7 C8 126.67(15) . . ?
C7 C8 C9 114.77(15) . . ?
O2 C9 N2 112.44(14) . . ?
O2 C9 C8 121.46(15) . . ?
N2 C9 C8 126.10(15) . . ?
C11 C10 O2 124.81(15) . . ?
C11 C10 C15 125.75(16) . . ?
O2 C10 C15 109.43(14) . . ?
C10 C11 C12 114.57(16) . . ?
C11 C12 C13 121.20(16) . . ?
C12 C13 C14 124.04(16) . . ?
C15 C14 C13 114.83(15) . . ?
C15 C14 C16 127.36(15) . . ?
C13 C14 C16 117.81(15) . . ?
C10 C15 C14 119.62(15) . . ?
C10 C15 N2 105.39(14) . . ?
C14 C15 N2 134.99(15) . . ?
N1 B1 N2 108.37(13) . . ?
N1 B1 Cl1 109.37(7) . 4_575 ?
N2 B1 Cl1 109.10(7) . 4_575 ?
N1 B1 Cl1 109.37(7) . . ?
N2 B1 Cl1 109.10(7) . . ?
Cl1 B1 Cl1 111.48(9) 4_575 . ?
C7 N1 C1 106.61(13) . . ?
C7 N1 B1 121.83(13) . . ?
C1 N1 B1 131.56(14) . . ?
C9 N2 C15 106.45(13) . . ?
C9 N2 B1 122.27(13) . . ?
C15 N2 B1 131.29(13) . . ?
C7 O1 C6 106.05(13) . . ?
C9 O2 C10 106.29(13) . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 2333151'
loop_
_audit_author_name
_audit_author_address
'Regine Herbst-Irmer'
;University of Goettingen
Germany
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 B Br2 N2 O2'
_chemical_formula_sum            'C17 H13 B Br2 N2 O2'
_chemical_formula_weight         447.92

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'
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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.877(2)
_cell_length_b                   14.447(3)
_cell_length_c                   7.970(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.81(2)
_cell_angle_gamma                90
_cell_volume                     790.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8421
_cell_measurement_theta_min      2.5615
_cell_measurement_theta_max      29.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.127
_exptl_absorpt_coefficient_mu    5.142
_shelx_estimated_absorpt_T_min   0.328
_shelx_estimated_absorpt_T_max   0.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.599980
_exptl_absorpt_correction_T_max  0.745941
_exptl_absorpt_process_details   'Twinabs Ver 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21013
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.561
_diffrn_reflns_theta_max         29.749
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4055
_reflns_number_gt                3507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.869
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2 v2012.2'
_computing_cell_refinement       'Bruker SAINT V8.40A'
_computing_data_reduction        'Bruker SAINT V8.40A'
_computing_structure_solution    'SHELXT(Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_refine_special_details          'Refined as a 4-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.1539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4055
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.51384(7) 0.04356(4) 0.85602(6) 0.01894(17) Uani 1 1 d . . . . .
C1 C 0.2435(9) 0.2793(4) 0.8231(8) 0.0149(13) Uani 1 1 d . . . . .
O1 O 0.2499(7) 0.2311(3) 0.3835(5) 0.0165(11) Uani 1 1 d . . . . .
Br2 Br 0.02239(7) 0.03841(4) 0.84172(6) 0.01700(15) Uani 1 1 d . . . . .
C2 C 0.2355(9) 0.3764(4) 0.8152(8) 0.0187(14) Uani 1 1 d . . . . .
H2 H 0.232738 0.409571 0.917942 0.022 Uiso 1 1 calc R U . . .
O2 O 0.2597(7) -0.0949(3) 0.3221(5) 0.0183(11) Uani 1 1 d . . . . .
C11 C 0.2540(10) -0.2582(5) 0.3970(8) 0.0197(15) Uani 1 1 d . . . . .
H11 H 0.251182 -0.278935 0.283728 0.024 Uiso 1 1 calc R U . . .
N1 N 0.2526(8) 0.1410(3) 0.6101(6) 0.0123(11) Uani 1 1 d . . . . .
B1 B 0.2607(10) 0.0487(6) 0.7060(7) 0.0147(11) Uani 1 1 d . . . . .
N2 N 0.2611(9) -0.0319(3) 0.5800(6) 0.0132(11) Uani 1 1 d . . . . .
C12 C 0.2541(12) -0.3183(5) 0.5302(9) 0.0213(17) Uani 1 1 d . . . . .
H12 H 0.252176 -0.383061 0.509699 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2438(12) 0.2879(5) 0.5193(8) 0.0157(12) Uani 1 1 d . . . . .
C14 C 0.2583(10) -0.1917(4) 0.7382(8) 0.0139(12) Uani 1 1 d . . . . .
C4 C 0.2390(12) 0.3835(5) 0.5135(9) 0.0195(17) Uani 1 1 d . . . . .
H4 H 0.240604 0.417015 0.411038 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2616(10) -0.1669(4) 0.9220(8) 0.0196(15) Uani 1 1 d . . . . .
H17A H 0.291790 -0.222175 0.990025 0.029 Uiso 1 1 calc R U . . .
H17B H 0.133814 -0.142757 0.947868 0.029 Uiso 1 1 calc R U . . .
H17C H 0.361356 -0.119592 0.947601 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2315(10) 0.4269(5) 0.6674(8) 0.0208(16) Uani 1 1 d . . . . .
H3 H 0.223454 0.492470 0.671938 0.025 Uiso 1 1 calc R U . . .
C15 C 0.2594(11) -0.1313(5) 0.6022(9) 0.0166(14) Uani 1 1 d . . . . .
C8 C 0.2566(10) 0.0687(5) 0.3349(8) 0.0220(15) Uani 1 1 d . . . . .
C7 C 0.2550(10) 0.1432(4) 0.4402(8) 0.0170(13) Uani 1 1 d . . . . .
C6 C 0.2465(10) 0.2351(4) 0.6656(7) 0.0153(15) Uani 1 1 d . . . . .
C10 C 0.2581(10) -0.1670(5) 0.4382(8) 0.0161(14) Uani 1 1 d . . . . .
C16 C 0.2438(10) 0.2349(4) 0.9947(7) 0.0179(15) Uani 1 1 d . . . . .
H16A H 0.258211 0.282852 1.081563 0.027 Uiso 1 1 calc R U . . .
H16B H 0.352708 0.191197 1.008901 0.027 Uiso 1 1 calc R U . . .
H16C H 0.120804 0.201772 1.004960 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2603(10) -0.0157(5) 0.4114(7) 0.0163(13) Uani 1 1 d . . . . .
H1 H 0.268(8) 0.070(4) 0.219(7) 0.013(16) Uiso 1 1 d . . . . .
C13 C 0.2570(11) -0.2860(5) 0.6956(8) 0.0205(14) Uani 1 1 d . . . . .
H13 H 0.258264 -0.330175 0.783903 0.025 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
Br1 B1 2.046(7) . ?
C1 C2 1.406(8) . ?
C1 C6 1.410(8) . ?
C1 C16 1.510(8) . ?
O1 C7 1.348(7) . ?
O1 C5 1.362(8) . ?
Br2 B1 2.028(6) . ?
C2 C3 1.384(8) . ?
O2 C9 1.348(7) . ?
O2 C10 1.394(8) . ?
C11 C10 1.357(9) . ?
C11 C12 1.372(9) . ?
N1 C7 1.356(8) . ?
N1 C6 1.431(8) . ?
N1 B1 1.537(9) . ?
B1 N2 1.538(8) . ?
N2 C9 1.363(8) . ?
N2 C15 1.447(8) . ?
C12 C13 1.397(9) . ?
C5 C4 1.382(9) . ?
C5 C6 1.393(8) . ?
C14 C15 1.391(9) . ?
C14 C13 1.404(8) . ?
C14 C17 1.507(8) . ?
C4 C3 1.381(9) . ?
C15 C10 1.404(9) . ?
C8 C9 1.362(9) . ?
C8 C7 1.365(9) . ?

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
C2 C1 C6 114.5(6) . . ?
C2 C1 C16 117.5(5) . . ?
C6 C1 C16 128.0(5) . . ?
C7 O1 C5 107.7(5) . . ?
C3 C2 C1 124.3(6) . . ?
C9 O2 C10 106.5(5) . . ?
C10 C11 C12 115.3(6) . . ?
C7 N1 C6 106.8(5) . . ?
C7 N1 B1 121.0(5) . . ?
C6 N1 B1 132.2(5) . . ?
N1 B1 N2 109.5(4) . . ?
N1 B1 Br2 109.0(4) . . ?
N2 B1 Br2 109.2(4) . . ?
N1 B1 Br1 108.9(4) . . ?
N2 B1 Br1 108.4(4) . . ?
Br2 B1 Br1 111.8(3) . . ?
C9 N2 C15 107.0(5) . . ?
C9 N2 B1 120.9(5) . . ?
C15 N2 B1 132.1(5) . . ?
C11 C12 C13 121.2(7) . . ?
O1 C5 C4 125.3(6) . . ?
O1 C5 C6 109.6(6) . . ?
C4 C5 C6 125.1(6) . . ?
C15 C14 C13 114.8(6) . . ?
C15 C14 C17 127.4(6) . . ?
C13 C14 C17 117.7(6) . . ?
C3 C4 C5 115.2(6) . . ?
C4 C3 C2 121.1(7) . . ?
C14 C15 C10 119.6(6) . . ?
C14 C15 N2 135.9(6) . . ?
C10 C15 N2 104.5(5) . . ?
C9 C8 C7 115.5(5) . . ?
O1 C7 N1 110.8(5) . . ?
O1 C7 C8 122.6(5) . . ?
N1 C7 C8 126.6(6) . . ?
C5 C6 C1 119.8(6) . . ?
C5 C6 N1 105.1(5) . . ?
C1 C6 N1 135.0(5) . . ?
C11 C10 O2 124.4(6) . . ?
C11 C10 C15 125.5(6) . . ?
O2 C10 C15 110.1(6) . . ?
O2 C9 C8 121.6(5) . . ?
O2 C9 N2 111.9(6) . . ?
C8 C9 N2 126.4(6) . . ?
C12 C13 C14 123.5(6) . . ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 2333149'
loop_
_audit_author_name
_audit_author_address
'Regine Herbst-Irmer'
;University of Goettingen
Germany
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 B F2 N2 O2'
_chemical_formula_sum            'C17 H13 B F2 N2 O2'
_chemical_formula_weight         326.10

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.378(3)
_cell_length_b                   6.800(2)
_cell_length_c                   13.574(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1419.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.649
_cell_measurement_theta_max      27.109

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7081
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microsource'
_diffrn_detector_type            'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34861
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.001
_diffrn_reflns_theta_max         27.114
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1707
_reflns_number_gt                1516
_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 APEX2 v2012.2'
_computing_cell_refinement       'Bruker SAINT V8.38A'
_computing_data_reduction        'Bruker SAINT V8.38A'
_computing_structure_solution    'SHELXT(Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0426P)²+0.9069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1707
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
F1 F 0.64084(5) 0.58296(12) 0.43298(5) 0.0227(2) Uani 1 1 d . . . . .
B1 B 0.68964(12) 0.750000 0.45186(14) 0.0174(4) Uani 1 2 d S T P . .
O1 O 0.91485(8) 0.750000 0.35053(9) 0.0211(3) Uani 1 2 d S T P . .
N1 N 0.77289(9) 0.750000 0.38645(10) 0.0174(3) Uani 1 2 d S T P . .
C1 C 0.78051(11) 0.750000 0.28241(12) 0.0168(4) Uani 1 2 d S T P . .
N2 N 0.72241(9) 0.750000 0.56130(10) 0.0171(3) Uani 1 2 d S T P . .
O2 O 0.81903(8) 0.750000 0.68505(9) 0.0210(3) Uani 1 2 d S T P . .
C2 C 0.71967(11) 0.750000 0.20551(13) 0.0186(4) Uani 1 2 d S T P . .
C3 C 0.75547(12) 0.750000 0.11085(13) 0.0202(4) Uani 1 2 d S T P . .
H3 H 0.716959 0.750000 0.056128 0.024 Uiso 1 2 calc R U P . .
C4 C 0.84489(12) 0.750000 0.09240(13) 0.0203(4) Uani 1 2 d S T P . .
H4 H 0.865078 0.750000 0.026258 0.024 Uiso 1 2 calc R U P . .
C5 C 0.90471(12) 0.750000 0.16895(13) 0.0202(4) Uani 1 2 d S T P . .
H5 H 0.965720 0.750000 0.157932 0.024 Uiso 1 2 calc R U P . .
C6 C 0.86912(12) 0.750000 0.26212(13) 0.0181(4) Uani 1 2 d S T P . .
C7 C 0.85417(11) 0.750000 0.42229(13) 0.0193(4) Uani 1 2 d S T P . .
C9 C 0.80716(12) 0.750000 0.58603(13) 0.0194(4) Uani 1 2 d S T P . .
C8 C 0.87669(12) 0.750000 0.52134(13) 0.0225(4) Uani 1 2 d S T P . .
H8 H 0.935415 0.750000 0.543060 0.027 Uiso 1 2 calc R U P . .
C10 C 0.73603(11) 0.750000 0.72626(13) 0.0182(4) Uani 1 2 d S T P . .
C11 C 0.71721(12) 0.750000 0.82553(13) 0.0211(4) Uani 1 2 d S T P . .
H11 H 0.761034 0.750000 0.874856 0.025 Uiso 1 2 calc R U P . .
C12 C 0.62848(13) 0.750000 0.84782(13) 0.0220(4) Uani 1 2 d S T P . .
H12 H 0.610506 0.750000 0.914781 0.026 Uiso 1 2 calc R U P . .
C13 C 0.56589(12) 0.750000 0.77354(13) 0.0205(4) Uani 1 2 d S T P . .
H13 H 0.506326 0.750000 0.792115 0.025 Uiso 1 2 calc R U P . .
C14 C 0.58623(11) 0.750000 0.67287(12) 0.0173(4) Uani 1 2 d S T P . .
C15 C 0.67513(11) 0.750000 0.65095(12) 0.0164(3) Uani 1 2 d S T P . .
C16 C 0.62266(12) 0.750000 0.21978(13) 0.0244(4) Uani 1 2 d S T P . .
H16A H 0.593989 0.774464 0.156485 0.037 Uiso 0.5 1 calc R U P . .
H16B H 0.606611 0.853516 0.266608 0.037 Uiso 0.5 1 calc R U P . .
H16C H 0.604198 0.622019 0.245557 0.037 Uiso 0.5 1 calc R U P . .
C17 C 0.51532(11) 0.750000 0.59686(13) 0.0213(4) Uani 1 2 d S T P . .
H17A H 0.527474 0.851113 0.547297 0.032 Uiso 0.5 1 calc R U P . .
H17B H 0.459484 0.778049 0.628702 0.032 Uiso 0.5 1 calc R U P . .
H17C H 0.512710 0.620839 0.564974 0.032 Uiso 0.5 1 calc R U P . .


_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 1.3853(13) . ?
B1 N1 1.558(2) . ?
B1 N2 1.569(2) . ?
O1 C7 1.349(2) . ?
O1 C6 1.391(2) . ?
N1 C7 1.341(2) . ?
N1 C1 1.417(2) . ?
C1 C6 1.390(2) . ?
C1 C2 1.402(2) . ?
N2 C9 1.346(2) . ?
N2 C15 1.418(2) . ?
O2 C9 1.356(2) . ?
O2 C10 1.393(2) . ?
C2 C3 1.398(2) . ?
C2 C16 1.504(2) . ?
C3 C4 1.398(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.378(2) . ?
C7 C8 1.388(2) . ?
C9 C8 1.384(3) . ?
C10 C11 1.378(2) . ?
C10 C15 1.387(2) . ?
C11 C12 1.398(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.402(2) . ?
C14 C15 1.399(2) . ?
C14 C17 1.501(2) . ?

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 F1 110.15(14) 7_575 . ?
F1 B1 N1 109.86(10) 7_575 . ?
F1 B1 N1 109.86(10) . . ?
F1 B1 N2 110.44(10) 7_575 . ?
F1 B1 N2 110.44(10) . . ?
N1 B1 N2 106.01(13) . . ?
C7 O1 C6 105.86(13) . . ?
C7 N1 C1 106.53(14) . . ?
C7 N1 B1 123.99(14) . . ?
C1 N1 B1 129.49(14) . . ?
C6 C1 C2 120.44(16) . . ?
C6 C1 N1 106.17(15) . . ?
C2 C1 N1 133.39(16) . . ?
C9 N2 C15 106.41(14) . . ?
C9 N2 B1 123.19(14) . . ?
C15 N2 B1 130.40(14) . . ?
C9 O2 C10 105.94(13) . . ?
C3 C2 C1 114.94(16) . . ?
C3 C2 C16 120.59(16) . . ?
C1 C2 C16 124.47(16) . . ?
C4 C3 C2 123.51(17) . . ?
C5 C4 C3 121.20(17) . . ?
C6 C5 C4 115.07(16) . . ?
C5 C6 C1 124.83(17) . . ?
C5 C6 O1 126.23(16) . . ?
C1 C6 O1 108.94(15) . . ?
N1 C7 O1 112.50(15) . . ?
N1 C7 C8 125.71(16) . . ?
O1 C7 C8 121.79(16) . . ?
N2 C9 O2 112.18(15) . . ?
N2 C9 C8 126.15(16) . . ?
O2 C9 C8 121.66(16) . . ?
C9 C8 C7 114.95(16) . . ?
C11 C10 C15 125.38(17) . . ?
C11 C10 O2 125.79(16) . . ?
C15 C10 O2 108.83(15) . . ?
C10 C11 C12 114.63(16) . . ?
C13 C12 C11 121.17(16) . . ?
C12 C13 C14 123.44(17) . . ?
C15 C14 C13 115.17(16) . . ?
C15 C14 C17 124.30(15) . . ?
C13 C14 C17 120.52(16) . . ?
C10 C15 C14 120.21(16) . . ?
C10 C15 N2 106.65(15) . . ?
C14 C15 N2 133.14(15) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048

