# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20180510a
_database_code_depnum_ccdc_archive 'CCDC 2010636'
loop_
_audit_author_name
_audit_author_address
'BODIPY b'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_audit_creation_date             2018-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 B Cl4 F2 N2'
_chemical_formula_sum            'C23 H19 B Cl4 F2 N2'
_chemical_formula_weight         514.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   14.694(3)
_cell_length_b                   16.305(3)
_cell_length_c                   9.870(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2364.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.160
_cell_measurement_theta_min      3.230
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.9139.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            37155
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         3.241
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1715
_reflns_number_total             2682
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0761P)²+1.4621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2A-C10 \\sim Cl2B-C10
 with sigma of 0.02
 F1A-B1 \\sim F1B-B1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2B) = Uanis(Cl2A)
4. Others
 Sof(Cl2B)=Sof(F1B)=1-FVAR(1)
 Sof(Cl2A)=Sof(F1A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C8(H8), C9(H9), C11(H11)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
Cl1 Cl 0.36268(7) 0.36948(5) 0.43005(10) 0.0770(4) Uani 1 1 d . . . . .
Cl2B Cl 0.696(4) 0.2934(19) 0.736(5) 0.0880(5) Uani 0.50(12) 1 d D . . A 2
F1B F 0.425(2) 0.063(3) 0.307(3) 0.091(6) Uani 0.50(12) 1 d D . . A 2
N1 N 0.53677(18) 0.15789(13) 0.3628(2) 0.0505(6) Uani 1 1 d . . . . .
C1 C 0.5736(2) 0.13579(18) 0.4800(3) 0.0560(8) Uani 1 1 d . . . . .
H1 H 0.581341 0.081808 0.508108 0.067 Uiso 1 1 calc R . . . .
C2 C 0.5991(2) 0.20471(17) 0.5557(3) 0.0488(7) Uani 1 1 d . . . . .
C3 C 0.5776(2) 0.27150(16) 0.4777(3) 0.0462(7) Uani 1 1 d . . . . .
H3 H 0.587836 0.326075 0.500433 0.055 Uiso 1 1 calc R . . . .
C4 C 0.5376(2) 0.24335(15) 0.3586(3) 0.0452(6) Uani 1 1 d . . . . .
C5 C 0.500000 0.2849(2) 0.250000 0.0413(8) Uani 1 2 d S T P . .
C6 C 0.500000 0.3760(2) 0.250000 0.0390(8) Uani 1 2 d S T P . .
C7 C 0.4400(2) 0.42026(16) 0.3287(3) 0.0478(7) Uani 1 1 d . . . . .
C8 C 0.4394(2) 0.50464(18) 0.3291(3) 0.0639(9) Uani 1 1 d . . . . .
H8 H 0.398034 0.533134 0.382772 0.077 Uiso 1 1 calc R . . . .
C9 C 0.500000 0.5460(3) 0.250000 0.0701(14) Uani 1 2 d S T P . .
H9 H 0.500000 0.603048 0.249999 0.084 Uiso 1 2 calc RS T P . .
C10 C 0.6399(2) 0.20331(19) 0.6908(3) 0.0542(7) Uani 1 1 d D . . . .
C11 C 0.6376(3) 0.1414(2) 0.7745(4) 0.0733(10) Uani 1 1 d . . . . .
H11 H 0.606395 0.095197 0.744701 0.088 Uiso 1 1 calc R . . . .
C12 C 0.6791(3) 0.1357(3) 0.9121(4) 0.0927(14) Uani 1 1 d . . . . .
H12A H 0.718852 0.182396 0.926276 0.111 Uiso 1 1 calc R . . . .
H12B H 0.631282 0.137954 0.979719 0.111 Uiso 1 1 calc R . . . .
C13 C 0.7318(3) 0.0596(3) 0.9306(5) 0.1016(15) Uani 1 1 d . . . . .
H13A H 0.786114 0.061998 0.876733 0.152 Uiso 1 1 calc GR . . . .
H13B H 0.695659 0.013489 0.902641 0.152 Uiso 1 1 calc GR . . . .
H13C H 0.747818 0.053597 1.024329 0.152 Uiso 1 1 calc GR . . . .
B1 B 0.500000 0.1010(3) 0.250000 0.0641(15) Uani 1 2 d DS T P . .
Cl2A Cl 0.696(4) 0.2936(19) 0.734(5) 0.0880(5) Uani 0.50(12) 1 d D . . A 1
F1A F 0.439(2) 0.0435(19) 0.292(4) 0.095(4) Uani 0.50(12) 1 d D . . A 1


_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
Cl1 C7 1.725(3) . ?
Cl2B C10 1.743(11) . ?
F1B B1 1.383(11) . ?
N1 C1 1.326(4) . ?
N1 C4 1.394(3) . ?
N1 B1 1.546(4) . ?
C1 C2 1.400(4) . ?
C2 C3 1.370(4) . ?
C2 C10 1.463(4) . ?
C3 C4 1.392(4) . ?
C4 C5 1.383(3) . ?
C5 C6 1.485(5) . ?
C6 C7 1.379(3) . ?
C6 C7 1.379(3) 4_655 ?
C7 C8 1.376(4) . ?
C8 C9 1.363(4) . ?
C10 C11 1.305(4) . ?
C10 Cl2A 1.743(11) . ?
C11 C12 1.492(5) . ?
C12 C13 1.474(5) . ?
B1 F1A 1.362(11) 4_655 ?
B1 F1A 1.362(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
C1 N1 C4 107.1(2) . . ?
C1 N1 B1 127.4(2) . . ?
C4 N1 B1 125.5(2) . . ?
N1 C1 C2 110.9(2) . . ?
C1 C2 C10 125.7(3) . . ?
C3 C2 C1 106.0(3) . . ?
C3 C2 C10 128.2(3) . . ?
C2 C3 C4 108.0(2) . . ?
C3 C4 N1 107.9(2) . . ?
C5 C4 N1 120.6(3) . . ?
C5 C4 C3 131.4(3) . . ?
C4 C5 C4 121.4(3) . 4_655 ?
C4 C5 C6 119.32(16) . . ?
C4 C5 C6 119.32(16) 4_655 . ?
C7 C6 C5 121.57(16) 4_655 . ?
C7 C6 C5 121.57(16) . . ?
C7 C6 C7 116.9(3) . 4_655 ?
C6 C7 Cl1 119.7(2) . . ?
C8 C7 Cl1 118.3(2) . . ?
C8 C7 C6 122.0(3) . . ?
C9 C8 C7 119.2(3) . . ?
C8 C9 C8 120.7(4) . 4_655 ?
C2 C10 Cl2B 114.5(16) . . ?
C2 C10 Cl2A 114.0(17) . . ?
C11 C10 Cl2B 120.1(16) . . ?
C11 C10 C2 125.4(3) . . ?
C11 C10 Cl2A 120.6(17) . . ?
C10 C11 C12 127.9(4) . . ?
C13 C12 C11 112.3(4) . . ?
F1B B1 F1B 127(5) 4_655 . ?
F1B B1 N1 104.7(14) . . ?
F1B B1 N1 106.4(19) 4_655 . ?
N1 B1 N1 106.3(3) . 4_655 ?
F1A B1 F1B 110(4) . 4_655 ?
F1A B1 F1B 17.0(15) 4_655 4_655 ?
F1A B1 N1 113.8(13) 4_655 . ?
F1A B1 N1 113.8(13) . 4_655 ?
F1A B1 N1 114.9(17) 4_655 4_655 ?
F1A B1 N1 114.9(17) . . ?
F1A B1 F1A 93(4) 4_655 . ?

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
Cl1 C7 C8 C9 179.9(2) . . . . ?
Cl2B C10 C11 C12 0(2) . . . . ?
N1 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C10 178.6(3) . . . . ?
N1 C4 C5 C4 -1.47(19) . . . 4_655 ?
N1 C4 C5 C6 178.53(19) . . . . ?
C1 N1 C4 C3 0.7(3) . . . . ?
C1 N1 C4 C5 -177.4(2) . . . . ?
C1 N1 B1 F1B -70(2) . . . 4_655 ?
C1 N1 B1 F1B 67(2) . . . . ?
C1 N1 B1 N1 179.0(3) . . . 4_655 ?
C1 N1 B1 F1A 52.1(18) . . . . ?
C1 N1 B1 F1A -53(2) . . . 4_655 ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C10 Cl2B 161(2) . . . . ?
C1 C2 C10 C11 -18.4(5) . . . . ?
C1 C2 C10 Cl2A 160(2) . . . . ?
C2 C3 C4 N1 -1.3(3) . . . . ?
C2 C3 C4 C5 176.4(3) . . . . ?
C2 C10 C11 C12 178.8(4) . . . . ?
C3 C2 C10 Cl2B -20(2) . . . . ?
C3 C2 C10 C11 161.2(4) . . . . ?
C3 C2 C10 Cl2A -20(2) . . . . ?
C3 C4 C5 C4 -179.0(4) . . . 4_655 ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 N1 C1 C2 0.2(4) . . . . ?
C4 N1 B1 F1B 110(2) . . . 4_655 ?
C4 N1 B1 F1B -114(2) . . . . ?
C4 N1 B1 N1 -1.5(2) . . . 4_655 ?
C4 N1 B1 F1A 126(2) . . . 4_655 ?
C4 N1 B1 F1A -128.4(18) . . . . ?
C4 C5 C6 C7 -75.9(2) . . . . ?
C4 C5 C6 C7 104.1(2) 4_655 . . . ?
C4 C5 C6 C7 -75.9(2) 4_655 . . 4_655 ?
C4 C5 C6 C7 104.1(2) . . . 4_655 ?
C5 C6 C7 Cl1 -0.1(3) . . . . ?
C5 C6 C7 C8 -179.8(2) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C7 C6 C7 Cl1 179.9(3) 4_655 . . . ?
C7 C6 C7 C8 0.2(2) 4_655 . . . ?
C7 C8 C9 C8 0.2(2) . . . 4_655 ?
C10 C2 C3 C4 -178.2(3) . . . . ?
C10 C11 C12 C13 -131.5(5) . . . . ?
B1 N1 C1 C2 179.8(2) . . . . ?
B1 N1 C4 C3 -178.9(2) . . . . ?
B1 N1 C4 C5 3.0(4) . . . . ?
Cl2A C10 C11 C12 0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_20181018e_0m
_database_code_depnum_ccdc_archive 'CCDC 2418848'
loop_
_audit_author_name
_audit_author_address
'lv fan'
;Anhui Normal University
China
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_audit_creation_date             2025-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H25 B Cl4 F2 N2'
_chemical_formula_sum            'C26 H25 B Cl4 F2 N2'
_chemical_formula_weight         556.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.744
_cell_length_b                   17.965
_cell_length_c                   9.147
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2751.6
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1053 before and 0.0540 after correction. The Ratio of minimum to maximum transmission is 0.9257. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull reddish red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            109216
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.179
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             2508
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.493
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0875
_refine_ls_restrained_S_all      1.080
_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)+(0.1705P)²+3.9562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2541
_refine_ls_wR_factor_ref         0.2792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.01
 C15, C14, C13
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C15, Cl2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.001
4. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C3(H3), C13(H13)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_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
Cl1 Cl 0.30411(8) 0.26406(7) 0.25623(13) 0.0737(5) Uani 1 1 d . . . . .
Cl2 Cl 0.24531(12) -0.01875(12) 0.1184(3) 0.1342(9) Uani 1 1 d . U . . .
F1 F 0.44190(19) 0.04226(15) 0.8121(3) 0.0830(9) Uani 1 1 d . . . . .
N1 N 0.46336(18) 0.13804(14) 0.6319(3) 0.0477(8) Uani 1 1 d . . . . .
C6 C 0.500000 0.3385(2) 0.750000 0.0388(10) Uani 1 2 d S T P . .
C7 C 0.500000 0.2547(2) 0.750000 0.0417(11) Uani 1 2 d S T P . .
C8 C 0.4619(2) 0.21674(17) 0.6376(4) 0.0447(8) Uani 1 1 d . . . . .
C9 C 0.4203(2) 0.24192(18) 0.5162(4) 0.0473(8) Uani 1 1 d . . . . .
H9 H 0.409724 0.291445 0.493877 0.057 Uiso 1 1 calc R . . . .
C10 C 0.3974(2) 0.18122(19) 0.4341(4) 0.0515(9) Uani 1 1 d . . . . .
C4 C 0.500000 0.4938(3) 0.750000 0.0616(15) Uani 1 2 d S T P . .
C2 C 0.5562(2) 0.37649(19) 0.6668(4) 0.0501(9) Uani 1 1 d . . . . .
C11 C 0.4254(3) 0.11798(19) 0.5105(4) 0.0545(9) Uani 1 1 d . . . . .
H11 H 0.418274 0.069053 0.479991 0.065 Uiso 1 1 calc R . . . .
C12 C 0.3536(3) 0.1801(2) 0.2952(5) 0.0576(10) Uani 1 1 d . . . . .
C3 C 0.5546(3) 0.4547(2) 0.6676(5) 0.0612(11) Uani 1 1 d . . . . .
H3 H 0.591379 0.480767 0.611132 0.073 Uiso 1 1 calc R . . . .
B1 B 0.500000 0.0868(3) 0.750000 0.0511(14) Uani 1 2 d S T P . .
C13 C 0.3495(4) 0.1243(3) 0.2016(7) 0.0878(15) Uani 1 1 d . U . . .
H13 H 0.377322 0.081483 0.227160 0.105 Uiso 1 1 calc R . . . .
C1 C 0.6175(3) 0.3355(3) 0.5783(7) 0.0805(14) Uani 1 1 d . . . . .
H1A H 0.648115 0.303674 0.641400 0.121 Uiso 1 1 calc GR . . . .
H1B H 0.652410 0.370589 0.531678 0.121 Uiso 1 1 calc GR . . . .
H1C H 0.591255 0.305894 0.505308 0.121 Uiso 1 1 calc GR . . . .
C5 C 0.500000 0.5780(3) 0.750000 0.104(3) Uani 1 2 d S T P . .
H5A H 0.552384 0.595773 0.774405 0.155 Uiso 0.5 1 calc GR . . A -1
H5B H 0.462262 0.595773 0.820845 0.155 Uiso 0.5 1 calc GR . . A -1
H5C H 0.485353 0.595773 0.654751 0.155 Uiso 0.5 1 calc GR . . A -1
C14 C 0.3056(4) 0.1217(4) 0.0597(7) 0.0947(15) Uani 1 1 d . U . . .
H14A H 0.339995 0.100364 -0.014687 0.114 Uiso 1 1 calc R . . . .
H14B H 0.292055 0.171914 0.029809 0.114 Uiso 1 1 calc R . . . .
C15 C 0.2272(5) 0.0741(5) 0.0720(9) 0.1146(15) Uani 1 1 d . U . . .
H15A H 0.199244 0.075683 -0.020809 0.138 Uiso 1 1 calc R . . . .
H15B H 0.192715 0.096126 0.145320 0.138 Uiso 1 1 calc R . . . .


_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
Cl1 C12 1.757(4) . ?
Cl2 C15 1.747(9) . ?
F1 B1 1.382(4) . ?
N1 C8 1.415(4) . ?
N1 C11 1.329(5) . ?
N1 B1 1.546(4) . ?
C6 C7 1.506(6) . ?
C6 C2 1.389(4) . ?
C6 C2 1.389(4) 3_656 ?
C7 C8 1.389(4) 3_656 ?
C7 C8 1.389(4) . ?
C8 C9 1.387(5) . ?
C9 C10 1.379(5) . ?
C10 C11 1.414(5) . ?
C10 C12 1.468(6) . ?
C4 C3 1.377(5) 3_656 ?
C4 C3 1.377(5) . ?
C4 C5 1.511(8) . ?
C2 C3 1.406(5) . ?
C2 C1 1.501(6) . ?
C12 C13 1.320(7) . ?
C13 C14 1.492(8) . ?
C14 C15 1.571(10) . ?

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
C8 N1 B1 125.1(3) . . ?
C11 N1 C8 107.1(3) . . ?
C11 N1 B1 127.7(3) . . ?
C2 C6 C7 119.4(2) 3_656 . ?
C2 C6 C7 119.4(2) . . ?
C2 C6 C2 121.2(4) 3_656 . ?
C8 C7 C6 119.4(2) 3_656 . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 C8 121.2(4) 3_656 . ?
C7 C8 N1 120.7(3) . . ?
C9 C8 N1 107.8(3) . . ?
C9 C8 C7 131.5(3) . . ?
C10 C9 C8 108.6(3) . . ?
C9 C10 C11 105.9(3) . . ?
C9 C10 C12 128.4(3) . . ?
C11 C10 C12 125.7(3) . . ?
C3 C4 C3 118.7(5) 3_656 . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 C5 120.7(2) 3_656 . ?
C6 C2 C3 118.4(4) . . ?
C6 C2 C1 121.2(3) . . ?
C3 C2 C1 120.4(4) . . ?
N1 C11 C10 110.7(3) . . ?
C10 C12 Cl1 113.6(3) . . ?
C13 C12 Cl1 119.7(4) . . ?
C13 C12 C10 126.7(4) . . ?
C4 C3 C2 121.7(4) . . ?
F1 B1 F1 109.2(5) 3_656 . ?
F1 B1 N1 110.65(17) 3_656 3_656 ?
F1 B1 N1 109.71(17) 3_656 . ?
F1 B1 N1 109.71(17) . 3_656 ?
F1 B1 N1 110.64(17) . . ?
N1 B1 N1 107.0(4) 3_656 . ?
C12 C13 C14 127.9(5) . . ?
C13 C14 C15 111.5(6) . . ?
C14 C15 Cl2 113.1(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
