# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_MM180208_0m
_database_code_depnum_ccdc_archive 'CCDC 1937169'
loop_
_audit_author_name
_audit_author_address
'Benjamin S. Gelfand'
;The University of Calgary
Canada
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 B2 N2 Cl4'
_chemical_formula_sum            'C24 H26 B2 Cl4 N2'
_chemical_formula_weight         505.89

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.8598(9)
_cell_length_b                   6.8679(10)
_cell_length_c                   17.032(3)
_cell_angle_alpha                92.380(7)
_cell_angle_beta                 94.987(7)
_cell_angle_gamma                108.870(6)
_cell_volume                     644.37(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2552
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             262
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.474
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4981
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6197
_diffrn_reflns_av_unetI/netI     0.1271
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2914
_reflns_number_gt                1857
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v. 5.9.8 (Spasyuk, 2009)'
_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)+(0.1123P)²] 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         2914
_refine_ls_number_parameters     148
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2176
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.983
_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
Cl1 Cl 0.66972(17) 0.75642(15) 0.43863(7) 0.0284(3) Uani 1 1 d . U . . .
Cl2 Cl 0.30125(18) 0.93048(14) 0.36123(7) 0.0301(3) Uani 1 1 d . U . . .
N1 N 0.1724(5) 0.6026(4) 0.4562(2) 0.0200(7) Uani 1 1 d . U . . .
C3 C 0.0542(7) 0.3632(6) 0.3478(2) 0.0225(8) Uani 1 1 d . U . . .
C2 C 0.0066(6) 0.4195(5) 0.4251(2) 0.0199(8) Uani 1 1 d . U . . .
C1 C 0.1703(7) 0.6813(6) 0.5270(2) 0.0224(8) Uani 1 1 d . U . . .
H1 H 0.2878 0.8058 0.5458 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2626(7) 0.5097(6) 0.3260(3) 0.0254(9) Uani 1 1 d . U . . .
C7 C 0.0133(8) 0.1635(7) 0.2280(3) 0.0302(10) Uani 1 1 d . U . . .
H7 H -0.0712 0.0479 0.1942 0.036 Uiso 1 1 calc R U . . .
C8 C -0.0739(7) 0.1897(6) 0.2974(3) 0.0267(9) Uani 1 1 d . U . . .
H8 H -0.2155 0.0945 0.3110 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3473(8) 0.4772(7) 0.2563(3) 0.0307(10) Uani 1 1 d . U . . .
H5 H 0.4886 0.5726 0.2426 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2262(8) 0.3035(6) 0.2051(3) 0.0289(9) Uani 1 1 d . U . . .
C9 C 0.3142(9) 0.2619(8) 0.1263(3) 0.0415(12) Uani 1 1 d . U . . .
C10 C 0.5586(10) 0.4199(10) 0.1146(3) 0.0533(15) Uani 1 1 d . U . . .
H10A H 0.5424 0.5543 0.1127 0.080 Uiso 1 1 calc R U . . .
H10B H 0.6112 0.3837 0.0658 0.080 Uiso 1 1 calc R U . . .
H10C H 0.6760 0.4209 0.1577 0.080 Uiso 1 1 calc R U . . .
C11 C 0.3423(11) 0.0475(9) 0.1237(4) 0.0532(14) Uani 1 1 d . U . . .
H11A H 0.4539 0.0410 0.1674 0.080 Uiso 1 1 calc R U . . .
H11B H 0.4031 0.0225 0.0750 0.080 Uiso 1 1 calc R U . . .
H11C H 0.1875 -0.0552 0.1269 0.080 Uiso 1 1 calc R U . . .
B1 B 0.3585(8) 0.6949(6) 0.3919(3) 0.0227(9) Uani 1 1 d . U . . .
C12 C 0.1243(11) 0.2716(11) 0.0589(3) 0.0568(15) Uani 1 1 d . U . . .
H12A H -0.0294 0.1702 0.0648 0.085 Uiso 1 1 calc R U . . .
H12B H 0.1760 0.2441 0.0088 0.085 Uiso 1 1 calc R U . . .
H12C H 0.1083 0.4064 0.0611 0.085 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
Cl1 B1 1.832(5) . ?
Cl2 B1 1.843(5) . ?
N1 C1 1.304(5) . ?
N1 C2 1.368(4) . ?
N1 B1 1.614(5) . ?
C3 C8 1.395(5) . ?
C3 C4 1.399(5) . ?
C3 C2 1.431(6) . ?
C2 C1 1.397(5) 2_566 ?
C1 C2 1.397(5) 2_566 ?
C1 H1 0.9300 . ?
C4 C5 1.364(6) . ?
C4 B1 1.582(6) . ?
C7 C8 1.355(6) . ?
C7 C6 1.405(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9300 . ?
C6 C9 1.527(6) . ?
C9 C10 1.527(7) . ?
C9 C11 1.533(8) . ?
C9 C12 1.548(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 C2 122.8(3) . . ?
C1 N1 B1 128.2(3) . . ?
C2 N1 B1 109.0(3) . . ?
C8 C3 C4 120.7(4) . . ?
C8 C3 C2 128.8(3) . . ?
C4 C3 C2 110.5(3) . . ?
N1 C2 C1 116.6(4) . 2_566 ?
N1 C2 C3 111.8(3) . . ?
C1 C2 C3 131.6(3) 2_566 . ?
N1 C1 C2 120.6(3) . 2_566 ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 2_566 . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 B1 131.2(3) . . ?
C3 C4 B1 109.4(3) . . ?
C8 C7 C6 122.7(4) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C3 118.3(4) . . ?
C7 C8 H8 120.9 . . ?
C3 C8 H8 120.9 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 117.5(4) . . ?
C5 C6 C9 122.9(4) . . ?
C7 C6 C9 119.6(4) . . ?
C10 C9 C6 112.3(4) . . ?
C10 C9 C11 108.2(5) . . ?
C6 C9 C11 109.1(4) . . ?
C10 C9 C12 108.7(5) . . ?
C6 C9 C12 108.4(4) . . ?
C11 C9 C12 110.2(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 B1 N1 99.0(3) . . ?
C4 B1 Cl1 117.8(3) . . ?
N1 B1 Cl1 108.9(3) . . ?
C4 B1 Cl2 112.9(3) . . ?
N1 B1 Cl2 106.3(3) . . ?
Cl1 B1 Cl2 110.6(2) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C1 N1 C2 C1 0.5(6) . . . 2_566 ?
B1 N1 C2 C1 -179.6(4) . . . 2_566 ?
C1 N1 C2 C3 -177.6(4) . . . . ?
B1 N1 C2 C3 2.3(5) . . . . ?
C8 C3 C2 N1 -179.6(4) . . . . ?
C4 C3 C2 N1 1.5(5) . . . . ?
C8 C3 C2 C1 2.5(8) . . . 2_566 ?
C4 C3 C2 C1 -176.3(4) . . . 2_566 ?
C2 N1 C1 C2 -0.6(7) . . . 2_566 ?
B1 N1 C1 C2 179.6(4) . . . 2_566 ?
C8 C3 C4 C5 -3.1(6) . . . . ?
C2 C3 C4 C5 175.9(4) . . . . ?
C8 C3 C4 B1 176.4(4) . . . . ?
C2 C3 C4 B1 -4.7(5) . . . . ?
C6 C7 C8 C3 -0.1(7) . . . . ?
C4 C3 C8 C7 2.2(6) . . . . ?
C2 C3 C8 C7 -176.6(4) . . . . ?
C3 C4 C5 C6 1.9(7) . . . . ?
B1 C4 C5 C6 -177.4(4) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C4 C5 C6 C9 179.7(4) . . . . ?
C8 C7 C6 C5 -1.0(7) . . . . ?
C8 C7 C6 C9 179.3(4) . . . . ?
C5 C6 C9 C10 5.3(7) . . . . ?
C7 C6 C9 C10 -175.1(5) . . . . ?
C5 C6 C9 C11 125.2(5) . . . . ?
C7 C6 C9 C11 -55.2(6) . . . . ?
C5 C6 C9 C12 -114.7(5) . . . . ?
C7 C6 C9 C12 64.9(6) . . . . ?
C5 C4 B1 N1 -175.2(4) . . . . ?
C3 C4 B1 N1 5.4(4) . . . . ?
C5 C4 B1 Cl1 -58.2(6) . . . . ?
C3 C4 B1 Cl1 122.5(3) . . . . ?
C5 C4 B1 Cl2 72.8(5) . . . . ?
C3 C4 B1 Cl2 -106.6(3) . . . . ?
C1 N1 B1 C4 175.4(4) . . . . ?
C2 N1 B1 C4 -4.6(4) . . . . ?
C1 N1 B1 Cl1 51.8(5) . . . . ?
C2 N1 B1 Cl1 -128.1(3) . . . . ?
C1 N1 B1 Cl2 -67.4(5) . . . . ?
C2 N1 B1 Cl2 112.7(3) . . . . ?

_refine_diff_density_max         0.940
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_83
_database_code_depnum_ccdc_archive 'CCDC 1937170'
loop_
_audit_author_name
_audit_author_address
'Benjamin S. Gelfand'
;The University of Calgary
Canada
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-03-07
_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         'C24 H17 B F6 N'
_chemical_formula_sum            'C24 H17 B F6 N'
_chemical_formula_weight         444.19
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0824(4)
_cell_length_b                   22.2704(10)
_cell_length_c                   10.3537(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.631(4)
_cell_angle_gamma                90
_cell_volume                     2094.10(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.118
_cell_measurement_theta_min      3.970
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0878 before and 0.0713 after correction. The Ratio of minimum to maximum transmission is 0.8761. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         1.984
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3287
_reflns_number_total             3653
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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         0.271
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.120
_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)+(0.1589P)²+0.4446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2218
_refine_ls_wR_factor_ref         0.2292
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.742(3)
 0.258(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C1(H1), C7(H7), C17(H17), C15(H15), C23(H23), C21(H21)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_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
F3 F 0.0558(3) 0.64122(12) 0.2385(3) 0.0422(6) Uani 1 1 d . . . . .
F6 F -0.0325(3) 0.53057(13) 0.3736(3) 0.0466(7) Uani 1 1 d . . . . .
F1 F 0.3162(3) 0.59867(13) 0.6245(3) 0.0439(7) Uani 1 1 d . . . . .
F2 F -0.0556(4) 0.74287(17) 0.6194(4) 0.0630(9) Uani 1 1 d . . . . .
F4 F 0.3891(4) 0.49325(17) 0.1291(4) 0.0641(10) Uani 1 1 d . . . . .
N1 N 0.3937(4) 0.52731(16) 0.4299(3) 0.0313(8) Uani 1 1 d . . . . .
F5 F -0.0530(5) 0.39712(18) 0.0287(4) 0.0783(12) Uani 1 1 d . . . . .
C2 C 0.5349(5) 0.54399(18) 0.4136(4) 0.0300(8) Uani 1 1 d . . . . .
C4 C 0.4079(5) 0.60228(19) 0.2599(4) 0.0325(9) Uani 1 1 d . . . . .
C3 C 0.5471(5) 0.58927(18) 0.3132(4) 0.0311(8) Uani 1 1 d . . . . .
C5 C 0.3991(5) 0.6426(2) 0.1572(4) 0.0348(9) Uani 1 1 d . . . . .
H5 H 0.305808 0.651781 0.119768 0.042 Uiso 1 1 calc R . . . .
C18 C 0.0826(5) 0.6504(2) 0.3662(4) 0.0349(9) Uani 1 1 d . . . . .
C19 C 0.1841(5) 0.51826(18) 0.2546(4) 0.0331(9) Uani 1 1 d . . . . .
C8 C 0.6755(5) 0.61620(19) 0.2682(4) 0.0315(8) Uani 1 1 d . . . . .
H8 H 0.769082 0.606986 0.305023 0.038 Uiso 1 1 calc R . . . .
C13 C 0.1905(5) 0.61453(18) 0.4250(4) 0.0305(8) Uani 1 1 d . . . . .
C1 C 0.3561(5) 0.48446(19) 0.5122(4) 0.0308(8) Uani 1 1 d . . . . .
H1 H 0.255755 0.473175 0.520636 0.037 Uiso 1 1 calc R . . . .
C6 C 0.5266(5) 0.67002(19) 0.1083(4) 0.0338(9) Uani 1 1 d . . . . .
C7 C 0.6612(5) 0.6569(2) 0.1676(4) 0.0334(9) Uani 1 1 d . . . . .
H7 H 0.746921 0.676707 0.137720 0.040 Uiso 1 1 calc R . . . .
C12 C 0.6355(7) 0.6965(3) -0.1064(5) 0.0505(12) Uani 1 1 d . . . . .
H12A H 0.731784 0.693507 -0.063184 0.076 Uiso 1 1 calc GR . . . .
H12B H 0.639332 0.727428 -0.173579 0.076 Uiso 1 1 calc GR . . . .
H12C H 0.610222 0.657777 -0.145687 0.076 Uiso 1 1 calc GR . . . .
C10 C 0.5182(6) 0.7134(2) -0.0070(4) 0.0386(10) Uani 1 1 d . . . . .
C16 C 0.0249(6) 0.7013(2) 0.5549(5) 0.0445(11) Uani 1 1 d . . . . .
C17 C -0.0022(5) 0.6929(2) 0.4252(5) 0.0421(11) Uani 1 1 d . . . . .
H17 H -0.075227 0.715187 0.379562 0.051 Uiso 1 1 calc R . . . .
C14 C 0.2103(5) 0.6283(2) 0.5542(4) 0.0339(9) Uani 1 1 d . . . . .
C15 C 0.1303(6) 0.6703(2) 0.6233(5) 0.0451(11) Uani 1 1 d . . . . .
H15 H 0.147579 0.677180 0.712709 0.054 Uiso 1 1 calc R . . . .
C24 C 0.0381(6) 0.5041(2) 0.2737(4) 0.0370(9) Uani 1 1 d . . . . .
C20 C 0.2443(6) 0.4861(2) 0.1527(5) 0.0423(11) Uani 1 1 d . . . . .
C23 C -0.0463(6) 0.4649(2) 0.2011(5) 0.0462(11) Uani 1 1 d . . . . .
H23 H -0.147307 0.458028 0.218706 0.055 Uiso 1 1 calc R . . . .
C22 C 0.0256(7) 0.4360(2) 0.1004(5) 0.0521(13) Uani 1 1 d . . . . .
C11 C 0.3676(7) 0.7132(3) -0.0741(5) 0.0527(13) Uani 1 1 d . . . . .
H11A H 0.345108 0.672588 -0.104838 0.079 Uiso 1 1 calc GR . . . .
H11B H 0.368943 0.740911 -0.147694 0.079 Uiso 1 1 calc GR . . . .
H11C H 0.292245 0.726031 -0.013009 0.079 Uiso 1 1 calc GR . . . .
B1 B 0.2814(5) 0.5664(2) 0.3372(4) 0.0309(9) Uani 1 1 d . . . . .
C21 C 0.1705(7) 0.4465(2) 0.0749(5) 0.0524(13) Uani 1 1 d . . . . .
H21 H 0.218318 0.426991 0.005388 0.063 Uiso 1 1 calc R . . . .
C9 C 0.5518(7) 0.7773(2) 0.0417(5) 0.0503(13) Uani 1 1 d . . . . .
H9A H 0.477412 0.789270 0.104527 0.075 Uiso 1 1 calc GR . . . .
H9B H 0.549984 0.805273 -0.031350 0.075 Uiso 1 1 calc GR . . . .
H9C H 0.649417 0.778007 0.082942 0.075 Uiso 1 1 calc GR . . . .


_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
F3 C18 1.357(5) . ?
F6 C24 1.357(6) . ?
F1 C14 1.369(5) . ?
F2 C16 1.360(6) . ?
F4 C20 1.349(7) . ?
N1 C2 1.348(6) . ?
N1 C1 1.326(6) . ?
N1 B1 1.643(5) . ?
F5 C22 1.341(6) . ?
C2 C3 1.453(5) . ?
C2 C1 1.399(6) 3_666 ?
C4 C3 1.404(6) . ?
C4 C5 1.394(6) . ?
C4 B1 1.618(6) . ?
C3 C8 1.397(6) . ?
C5 C6 1.409(7) . ?
C18 C13 1.398(6) . ?
C18 C17 1.369(6) . ?
C19 C24 1.380(7) . ?
C19 C20 1.392(6) . ?
C19 B1 1.626(6) . ?
C8 C7 1.386(6) . ?
C13 C14 1.383(6) . ?
C13 B1 1.634(6) . ?
C6 C7 1.392(7) . ?
C6 C10 1.537(5) . ?
C12 C10 1.536(7) . ?
C10 C11 1.527(7) . ?
C10 C9 1.538(7) . ?
C16 C17 1.375(7) . ?
C16 C15 1.370(7) . ?
C14 C15 1.387(7) . ?
C24 C23 1.379(7) . ?
C20 C21 1.365(8) . ?
C23 C22 1.395(8) . ?
C22 C21 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 N1 B1 111.5(3) . . ?
C1 N1 C2 122.1(4) . . ?
C1 N1 B1 126.4(4) . . ?
N1 C2 C3 111.2(4) . . ?
N1 C2 C1 118.4(4) . 3_666 ?
C1 C2 C3 130.4(4) 3_666 . ?
C3 C4 B1 110.2(4) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 B1 131.3(4) . . ?
C4 C3 C2 110.4(4) . . ?
C8 C3 C2 127.4(4) . . ?
C8 C3 C4 122.1(4) . . ?
C4 C5 C6 120.9(4) . . ?
F3 C18 C13 117.1(4) . . ?
F3 C18 C17 116.3(4) . . ?
C17 C18 C13 126.6(4) . . ?
C24 C19 C20 112.2(4) . . ?
C24 C19 B1 126.3(4) . . ?
C20 C19 B1 121.5(4) . . ?
C7 C8 C3 117.4(4) . . ?
C18 C13 B1 119.2(4) . . ?
C14 C13 C18 112.2(4) . . ?
C14 C13 B1 128.5(4) . . ?
N1 C1 C2 119.5(4) . 3_666 ?
C5 C6 C10 121.2(4) . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 C10 120.7(4) . . ?
C8 C7 C6 123.0(4) . . ?
C6 C10 C9 108.6(3) . . ?
C12 C10 C6 109.6(4) . . ?
C12 C10 C9 108.0(4) . . ?
C11 C10 C6 112.8(4) . . ?
C11 C10 C12 108.6(4) . . ?
C11 C10 C9 109.0(4) . . ?
F2 C16 C17 118.7(5) . . ?
F2 C16 C15 117.7(5) . . ?
C15 C16 C17 123.6(5) . . ?
C18 C17 C16 115.7(4) . . ?
F1 C14 C13 119.4(4) . . ?
F1 C14 C15 114.8(4) . . ?
C13 C14 C15 125.8(4) . . ?
C16 C15 C14 116.1(4) . . ?
F6 C24 C19 118.3(4) . . ?
F6 C24 C23 115.2(4) . . ?
C23 C24 C19 126.5(5) . . ?
F4 C20 C19 117.9(5) . . ?
F4 C20 C21 116.3(5) . . ?
C21 C20 C19 125.8(5) . . ?
C24 C23 C22 116.0(5) . . ?
F5 C22 C23 117.5(6) . . ?
F5 C22 C21 120.8(5) . . ?
C21 C22 C23 121.7(5) . . ?
C4 B1 N1 96.4(3) . . ?
C4 B1 C19 116.7(3) . . ?
C4 B1 C13 108.5(3) . . ?
C19 B1 N1 106.7(3) . . ?
C19 B1 C13 116.7(4) . . ?
C13 B1 N1 109.7(3) . . ?
C20 C21 C22 117.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.742(3)
2 0.258(3)

