# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2Cl
_database_code_depnum_ccdc_archive 'CCDC 2357740'
loop_
_audit_author_name
_audit_author_address
'Harie Zacharias'
;Baylor University
United States of America
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2Cl
_chemical_name_common            ?
_chemical_melting_point          370.15
_chemical_formula_moiety         C14H8BCl
_chemical_formula_sum            'C14 H8 B Cl'
_chemical_formula_weight         222.46

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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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                   8.5508(5)
_cell_length_b                   3.8729(3)
_cell_length_c                   15.8451(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.727(3)
_cell_angle_gamma                90
_cell_volume                     511.84(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6939
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      29.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.332
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_process_details   SADabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            9979
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2491
_reflns_number_gt                2267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.988

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion 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)+(0.1057P)²+1.0363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'DIRECT METHODS'
_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_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2491
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2273
_refine_ls_wR_factor_gt          0.2234
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.227
_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
B1 B 0.9111(9) 0.6745(19) 0.8265(5) 0.0195(14) Uani 1 1 d . . . . .
C1 C 0.9068(8) 0.5319(16) 0.7326(4) 0.0173(13) Uani 1 1 d . . . . .
C2 C 0.7500(7) 0.397(2) 0.7045(4) 0.0199(13) Uani 1 1 d . . . . .
C3 C 0.6546(8) 0.4393(14) 0.7675(4) 0.0174(13) Uani 1 1 d . . . . .
C4 C 0.7437(8) 0.6082(16) 0.8445(4) 0.0173(13) Uani 1 1 d . . . . .
C5 C 1.0063(8) 0.5023(17) 0.6746(5) 0.0227(15) Uani 1 1 d . . . . .
H5 H 1.113414 0.585469 0.689439 0.027 Uiso 1 1 calc R U . . .
C6 C 0.9449(8) 0.343(2) 0.5909(4) 0.0258(15) Uani 1 1 d . . . . .
H6 H 1.012403 0.325859 0.550815 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7950(9) 0.219(2) 0.5689(4) 0.0254(15) Uani 1 1 d . . . . .
H7 H 0.759412 0.109619 0.514311 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6891(9) 0.2478(17) 0.6257(5) 0.0219(14) Uani 1 1 d . . . . .
C9 C 0.4982(8) 0.3325(18) 0.7539(4) 0.0211(14) Uani 1 1 d . . . . .
C10 C 0.4203(8) 0.395(2) 0.8226(5) 0.0260(14) Uani 1 1 d . . . . .
H10 H 0.312141 0.324795 0.817338 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5004(9) 0.5580(19) 0.8969(5) 0.0255(16) Uani 1 1 d . . . . .
H11 H 0.444604 0.600556 0.941463 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6610(8) 0.6637(17) 0.9095(4) 0.0194(13) Uani 1 1 d . . . . .
H12 H 0.712563 0.772071 0.962094 0.023 Uiso 1 1 calc R U . . .
C13 C 0.5222(8) 0.1316(17) 0.6110(4) 0.0203(14) Uani 1 1 d . . . . .
H13 H 0.475125 0.025138 0.557379 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4332(8) 0.1699(19) 0.6705(5) 0.0260(15) Uani 1 1 d . . . . .
H14 H 0.325602 0.089311 0.657990 0.031 Uiso 1 1 calc R U . . .
Cl1 Cl 1.07418(19) 0.8686(5) 0.89606(11) 0.0291(5) 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
B1 C4 1.541(10) . ?
B1 C1 1.580(10) . ?
B1 Cl1 1.746(8) . ?
C1 C5 1.389(9) . ?
C1 C2 1.417(9) . ?
C2 C8 1.370(10) . ?
C2 C3 1.431(8) . ?
C3 C9 1.371(9) . ?
C3 C4 1.444(10) . ?
C4 C12 1.389(9) . ?
C5 C6 1.453(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.341(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(10) . ?
C7 H7 0.9500 . ?
C8 C13 1.465(10) . ?
C9 C10 1.416(9) . ?
C9 C14 1.459(10) . ?
C10 C11 1.377(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.344(10) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 B1 C1 106.6(6) . . ?
C4 B1 Cl1 126.9(6) . . ?
C1 B1 Cl1 126.5(5) . . ?
C5 C1 C2 115.9(6) . . ?
C5 C1 B1 139.7(6) . . ?
C2 C1 B1 104.4(5) . . ?
C8 C2 C1 125.9(6) . . ?
C8 C2 C3 121.6(6) . . ?
C1 C2 C3 112.5(6) . . ?
C9 C3 C2 122.8(6) . . ?
C9 C3 C4 125.7(6) . . ?
C2 C3 C4 111.5(6) . . ?
C12 C4 C3 115.9(6) . . ?
C12 C4 B1 139.2(7) . . ?
C3 C4 B1 104.9(5) . . ?
C1 C5 C6 119.2(6) . . ?
C1 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 121.5(5) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 121.0(7) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C2 C8 C7 116.4(6) . . ?
C2 C8 C13 115.8(6) . . ?
C7 C8 C13 127.7(7) . . ?
C3 C9 C10 115.8(6) . . ?
C3 C9 C14 115.9(6) . . ?
C10 C9 C14 128.3(6) . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 122.8(6) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C4 C12 C11 119.4(7) . . ?
C4 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C8 122.5(6) . . ?
C14 C13 H13 118.8 . . ?
C8 C13 H13 118.8 . . ?
C13 C14 C9 121.4(6) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?

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
C4 B1 C1 C5 179.6(8) . . . . ?
Cl1 B1 C1 C5 -0.5(12) . . . . ?
C4 B1 C1 C2 -0.9(7) . . . . ?
Cl1 B1 C1 C2 179.0(6) . . . . ?
C5 C1 C2 C8 -1.3(10) . . . . ?
B1 C1 C2 C8 179.1(7) . . . . ?
C5 C1 C2 C3 -179.5(6) . . . . ?
B1 C1 C2 C3 0.8(7) . . . . ?
C8 C2 C3 C9 0.7(10) . . . . ?
C1 C2 C3 C9 179.0(6) . . . . ?
C8 C2 C3 C4 -178.8(6) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C9 C3 C4 C12 0.1(9) . . . . ?
C2 C3 C4 C12 179.6(6) . . . . ?
C9 C3 C4 B1 -179.6(6) . . . . ?
C2 C3 C4 B1 -0.1(7) . . . . ?
C1 B1 C4 C12 -179.1(7) . . . . ?
Cl1 B1 C4 C12 1.0(12) . . . . ?
C1 B1 C4 C3 0.6(6) . . . . ?
Cl1 B1 C4 C3 -179.3(5) . . . . ?
C2 C1 C5 C6 0.6(9) . . . . ?
B1 C1 C5 C6 -179.9(8) . . . . ?
C1 C5 C6 C7 -1.0(11) . . . . ?
C5 C6 C7 C8 1.9(11) . . . . ?
C1 C2 C8 C7 2.1(10) . . . . ?
C3 C2 C8 C7 -179.8(6) . . . . ?
C1 C2 C8 C13 -179.1(6) . . . . ?
C3 C2 C8 C13 -1.0(10) . . . . ?
C6 C7 C8 C2 -2.3(10) . . . . ?
C6 C7 C8 C13 179.0(7) . . . . ?
C2 C3 C9 C10 -179.7(7) . . . . ?
C4 C3 C9 C10 -0.3(9) . . . . ?
C2 C3 C9 C14 0.1(9) . . . . ?
C4 C3 C9 C14 179.5(6) . . . . ?
C3 C9 C10 C11 0.7(10) . . . . ?
C14 C9 C10 C11 -179.0(7) . . . . ?
C9 C10 C11 C12 -1.1(11) . . . . ?
C3 C4 C12 C11 -0.4(9) . . . . ?
B1 C4 C12 C11 179.2(7) . . . . ?
C10 C11 C12 C4 1.0(10) . . . . ?
C2 C8 C13 C14 0.5(10) . . . . ?
C7 C8 C13 C14 179.2(7) . . . . ?
C8 C13 C14 C9 0.3(11) . . . . ?
C3 C9 C14 C13 -0.5(10) . . . . ?
C10 C9 C14 C13 179.2(7) . . . . ?

_refine_diff_density_max         0.958
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.148


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene, Hexanes'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_3Ph
_database_code_depnum_ccdc_archive 'CCDC 2357741'
loop_
_audit_author_name
_audit_author_address
'Harie Zacharias'
;Baylor University
United States of America
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3Ph
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C21H15BClN
_chemical_formula_sum            'C21 H15 B Cl N'
_chemical_formula_weight         327.60

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.4556(3)
_cell_length_b                   16.6414(13)
_cell_length_c                   17.5759(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1595.70(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.08

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   SADabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            43931
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.621
_diffrn_reflns_theta_max         26.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3377
_reflns_number_gt                3222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0409P)²+0.5194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'DIRECT METHODS'
_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_abs_structure_details 
; 
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3377
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_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 0.99795(13) 0.61612(4) 0.78218(4) 0.03343(17) Uani 1 1 d . . . . .
B1 B 0.8049(5) 0.68459(16) 0.73149(14) 0.0222(5) Uani 1 1 d . . . . .
N1 N 0.8240(4) 0.76774(12) 0.74439(11) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.4758(4) 0.79252(13) 0.65891(12) 0.0199(5) Uani 1 1 d . . . . .
C4 C 0.6124(5) 0.65174(15) 0.67638(14) 0.0227(5) Uani 1 1 d . . . . .
C3 C 0.4481(4) 0.70837(14) 0.64365(13) 0.0197(5) Uani 1 1 d . . . . .
C1 C 0.6623(4) 0.82231(14) 0.70806(13) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.2564(4) 0.68116(16) 0.59560(13) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.2376(5) 0.59851(16) 0.58001(14) 0.0279(6) Uani 1 1 d . . . . .
H10 H 0.108748 0.579729 0.548283 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3106(5) 0.84762(15) 0.62451(13) 0.0235(5) Uani 1 1 d . . . . .
C5 C 0.6808(5) 0.90486(15) 0.72020(14) 0.0276(5) Uani 1 1 d . . . . .
H5 H 0.803654 0.924962 0.753441 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5874(5) 0.57097(16) 0.65737(15) 0.0276(5) Uani 1 1 d . . . . .
H12 H 0.700278 0.533039 0.677485 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3374(5) 0.93042(16) 0.63772(14) 0.0293(6) Uani 1 1 d . . . . .
H7 H 0.228043 0.967435 0.614440 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4013(5) 0.54458(16) 0.60969(15) 0.0299(6) Uani 1 1 d . . . . .
H11 H 0.387458 0.489114 0.597640 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5226(6) 0.95809(14) 0.68455(14) 0.0306(6) Uani 1 1 d . . . . .
H6 H 0.541800 1.014221 0.692384 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1159(5) 0.81732(17) 0.57763(14) 0.0267(5) Uani 1 1 d . . . . .
H13 H 0.003281 0.854113 0.555598 0.032 Uiso 1 1 calc R U . . .
C14 C 0.0886(5) 0.73821(16) 0.56405(14) 0.0268(5) Uani 1 1 d . . . . .
H14 H -0.043391 0.720101 0.533230 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0180(5) 0.80190(14) 0.79313(13) 0.0242(5) Uani 1 1 d . . . . .
H15A H 1.091105 0.848543 0.766522 0.029 Uiso 1 1 calc R U . . .
H15B H 1.148551 0.761116 0.799425 0.029 Uiso 1 1 calc R U . . .
C18 C 1.0320(6) 0.90345(16) 0.98511(15) 0.0343(6) Uani 1 1 d . . . . .
H18 H 1.138939 0.938432 1.012002 0.041 Uiso 1 1 calc R U . . .
C17 C 1.0874(5) 0.88050(15) 0.91133(14) 0.0263(5) Uani 1 1 d . . . . .
H17 H 1.231875 0.900431 0.887803 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9351(4) 0.82884(14) 0.87125(13) 0.0200(5) Uani 1 1 d . . . . .
C19 C 0.8199(6) 0.87525(18) 1.01972(15) 0.0371(7) Uani 1 1 d . . . . .
H19 H 0.781047 0.890863 1.070299 0.044 Uiso 1 1 calc R U . . .
C20 C 0.6662(5) 0.82450(17) 0.98024(15) 0.0316(6) Uani 1 1 d . . . . .
H20 H 0.520673 0.805349 1.003746 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7222(5) 0.80098(15) 0.90612(14) 0.0249(5) Uani 1 1 d . . . . .
H21 H 0.615033 0.765937 0.879384 0.030 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 1.789(3) . ?
B1 N1 1.406(3) . ?
B1 C4 1.530(4) . ?
N1 C1 1.418(3) . ?
N1 C15 1.476(3) . ?
C2 C8 1.421(3) . ?
C2 C1 1.424(3) . ?
C2 C3 1.434(3) . ?
C4 C12 1.392(4) . ?
C4 C3 1.422(3) . ?
C3 C9 1.418(3) . ?
C1 C5 1.394(3) . ?
C9 C10 1.406(4) . ?
C9 C14 1.431(4) . ?
C10 C11 1.370(4) . ?
C8 C7 1.405(4) . ?
C8 C13 1.436(4) . ?
C5 C6 1.386(4) . ?
C12 C11 1.388(4) . ?
C7 C6 1.382(4) . ?
C13 C14 1.346(4) . ?
C15 C16 1.513(3) . ?
C18 C17 1.385(4) . ?
C18 C19 1.389(4) . ?
C17 C16 1.388(3) . ?
C16 C21 1.393(3) . ?
C19 C20 1.378(4) . ?
C20 C21 1.394(4) . ?

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
N1 B1 C4 120.3(2) . . ?
N1 B1 Cl1 120.19(19) . . ?
C4 B1 Cl1 119.45(19) . . ?
B1 N1 C1 120.8(2) . . ?
B1 N1 C15 121.7(2) . . ?
C1 N1 C15 117.44(19) . . ?
C8 C2 C1 119.1(2) . . ?
C8 C2 C3 118.9(2) . . ?
C1 C2 C3 121.9(2) . . ?
C12 C4 C3 118.8(2) . . ?
C12 C4 B1 124.4(2) . . ?
C3 C4 B1 116.9(2) . . ?
C9 C3 C4 119.6(2) . . ?
C9 C3 C2 120.1(2) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C1 N1 121.2(2) . . ?
C5 C1 C2 119.2(2) . . ?
N1 C1 C2 119.7(2) . . ?
C10 C9 C3 118.8(2) . . ?
C10 C9 C14 121.8(2) . . ?
C3 C9 C14 119.4(2) . . ?
C11 C10 C9 121.3(2) . . ?
C7 C8 C2 119.8(2) . . ?
C7 C8 C13 121.1(2) . . ?
C2 C8 C13 119.1(2) . . ?
C6 C5 C1 121.0(2) . . ?
C11 C12 C4 121.5(2) . . ?
C6 C7 C8 120.1(2) . . ?
C10 C11 C12 120.0(2) . . ?
C7 C6 C5 120.8(2) . . ?
C14 C13 C8 121.8(2) . . ?
C13 C14 C9 120.6(2) . . ?
N1 C15 C16 115.2(2) . . ?
C17 C18 C19 119.9(3) . . ?
C18 C17 C16 121.0(2) . . ?
C17 C16 C21 118.8(2) . . ?
C17 C16 C15 117.7(2) . . ?
C21 C16 C15 123.4(2) . . ?
C20 C19 C18 119.6(2) . . ?
C19 C20 C21 120.6(3) . . ?
C16 C21 C20 120.0(2) . . ?

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
C4 B1 N1 C1 1.4(3) . . . . ?
Cl1 B1 N1 C1 -176.20(17) . . . . ?
C4 B1 N1 C15 -175.8(2) . . . . ?
Cl1 B1 N1 C15 6.5(3) . . . . ?
N1 B1 C4 C12 176.9(2) . . . . ?
Cl1 B1 C4 C12 -5.5(3) . . . . ?
N1 B1 C4 C3 -3.9(3) . . . . ?
Cl1 B1 C4 C3 173.79(17) . . . . ?
C12 C4 C3 C9 3.0(3) . . . . ?
B1 C4 C3 C9 -176.3(2) . . . . ?
C12 C4 C3 C2 -176.9(2) . . . . ?
B1 C4 C3 C2 3.8(3) . . . . ?
C8 C2 C3 C9 -0.7(3) . . . . ?
C1 C2 C3 C9 178.7(2) . . . . ?
C8 C2 C3 C4 179.1(2) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
B1 N1 C1 C5 -179.7(2) . . . . ?
C15 N1 C1 C5 -2.3(3) . . . . ?
B1 N1 C1 C2 1.1(3) . . . . ?
C15 N1 C1 C2 178.4(2) . . . . ?
C8 C2 C1 C5 -1.0(3) . . . . ?
C3 C2 C1 C5 179.6(2) . . . . ?
C8 C2 C1 N1 178.2(2) . . . . ?
C3 C2 C1 N1 -1.1(3) . . . . ?
C4 C3 C9 C10 -1.5(3) . . . . ?
C2 C3 C9 C10 178.3(2) . . . . ?
C4 C3 C9 C14 178.8(2) . . . . ?
C2 C3 C9 C14 -1.4(3) . . . . ?
C3 C9 C10 C11 -0.6(4) . . . . ?
C14 C9 C10 C11 179.1(2) . . . . ?
C1 C2 C8 C7 1.7(3) . . . . ?
C3 C2 C8 C7 -178.9(2) . . . . ?
C1 C2 C8 C13 -177.3(2) . . . . ?
C3 C2 C8 C13 2.1(3) . . . . ?
N1 C1 C5 C6 179.9(2) . . . . ?
C2 C1 C5 C6 -0.8(4) . . . . ?
C3 C4 C12 C11 -2.3(4) . . . . ?
B1 C4 C12 C11 176.9(2) . . . . ?
C2 C8 C7 C6 -0.5(4) . . . . ?
C13 C8 C7 C6 178.4(2) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C4 C12 C11 C10 0.2(4) . . . . ?
C8 C7 C6 C5 -1.3(4) . . . . ?
C1 C5 C6 C7 2.0(4) . . . . ?
C7 C8 C13 C14 179.6(2) . . . . ?
C2 C8 C13 C14 -1.4(3) . . . . ?
C8 C13 C14 C9 -0.7(4) . . . . ?
C10 C9 C14 C13 -177.6(2) . . . . ?
C3 C9 C14 C13 2.1(4) . . . . ?
B1 N1 C15 C16 -104.4(3) . . . . ?
C1 N1 C15 C16 78.3(3) . . . . ?
C19 C18 C17 C16 -0.6(4) . . . . ?
C18 C17 C16 C21 0.9(4) . . . . ?
C18 C17 C16 C15 -175.6(2) . . . . ?
N1 C15 C16 C17 -162.7(2) . . . . ?
N1 C15 C16 C21 21.0(3) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C17 C16 C21 C20 -0.5(4) . . . . ?
C15 C16 C21 C20 175.7(2) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040



#===END


_exptl_crystal_recrystallization_method 
'Vapor diffusion of Chloroform into Toluene'
