# Supplementary Information (SI) for Chemical Science.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2004799'
loop_
_audit_author_name
_audit_author_address
'Tamas Holczbauer'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2024-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C18 H10 B Cl5 F O 1-, C5 H12 N 1+, C5 H11 N
;
_chemical_formula_sum            'C28 H33 B Cl5 F N2 O'
_chemical_formula_weight         620.62

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.5595(2)
_cell_length_b                   18.0868(4)
_cell_length_c                   18.9345(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.522(7)
_cell_angle_gamma                90
_cell_volume                     2890.94(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    131696
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      29.095

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.534
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.958676
_exptl_absorpt_correction_T_max  0.986656
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_radiation_detector       RX
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            116433
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         3.025
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5286
_reflns_number_gt                5089
_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       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
# Spek, A. L. (2009). Acta Cryst. D65, 148--155. 
_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)+(0.0444P)²+3.6442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5286
_refine_ls_number_parameters     410
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.189
_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
Cl2 Cl 1.32900(7) 0.25943(4) 0.12875(4) 0.02958(16) Uani 1 1 d . . . . .
Cl3 Cl 1.02192(9) 0.17579(4) -0.09227(3) 0.03600(18) Uani 1 1 d . . . . .
Cl1 Cl 0.72723(8) 0.22157(4) 0.19054(4) 0.03560(18) Uani 1 1 d . . . . .
Cl4 Cl 0.99032(11) 0.39126(4) 0.10963(4) 0.0459(2) Uani 1 1 d . . . . .
Cl5A Cl 0.8315(5) 0.0466(2) 0.0948(3) 0.0452(5) Uani 0.6 1 d . . P A 1
F1A F 0.7172(15) 0.3220(7) 0.0170(5) 0.0433(7) Uani 0.4 1 d . . P A 1
F1B F 0.8547(13) 0.0553(6) 0.0960(8) 0.0452(5) Uani 0.6 1 d . . P B 2
Cl5B Cl 0.6925(6) 0.3143(2) -0.00199(17) 0.0433(7) Uani 0.4 1 d . . P B 2
O1 O 1.0850(2) 0.14879(9) 0.06388(9) 0.0227(4) Uani 1 1 d . . . . .
H1O H 1.066781 0.129120 0.023461 0.058(11) Uiso 1 1 d R . . . .
C1 C 1.0280(3) 0.23279(13) 0.15625(13) 0.0211(5) Uani 1 1 d . . . . .
C2 C 0.9340(3) 0.22865(14) 0.21012(14) 0.0247(5) Uani 1 1 d . . . . .
C3 C 0.9911(3) 0.23220(14) 0.28336(14) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.920517 0.227569 0.316893 0.040 Uiso 1 1 calc R U . . .
C4 C 1.1511(3) 0.24248(15) 0.30682(14) 0.0306(6) Uani 1 1 d . . . . .
H4 H 1.192206 0.243847 0.356575 0.043 Uiso 1 1 calc R U . . .
C5 C 1.2499(3) 0.25071(14) 0.25707(14) 0.0277(6) Uani 1 1 d . . . . .
H5 H 1.359694 0.259680 0.272092 0.039 Uiso 1 1 calc R U . . .
C6 C 1.1881(3) 0.24582(13) 0.18489(13) 0.0231(5) Uani 1 1 d . . . . .
C7 C 1.0249(3) 0.27992(14) 0.01484(13) 0.0226(5) Uani 1 1 d . . . . .
C8 C 1.0551(3) 0.26513(15) -0.05418(14) 0.0272(6) Uani 1 1 d . . . . .
C9 C 1.1061(3) 0.31573(19) -0.10063(15) 0.0381(7) Uani 1 1 d . . . . .
H9 H 1.124714 0.300844 -0.146635 0.053 Uiso 1 1 calc R U . . .
C10 C 1.1292(3) 0.38820(19) -0.07836(17) 0.0427(8) Uani 1 1 d . . . . .
H10 H 1.167391 0.423700 -0.108344 0.060 Uiso 1 1 calc R U . . .
C11 C 1.0964(4) 0.40848(17) -0.01235(17) 0.0397(7) Uani 1 1 d . . . . .
H11 H 1.109531 0.458348 0.003249 0.056 Uiso 1 1 calc R U . . .
C12 C 1.0442(3) 0.35574(15) 0.03106(15) 0.0304(6) Uani 1 1 d . . . . .
C13A C 0.792(3) 0.1945(10) 0.0408(13) 0.019(2) Uani 0.6 1 d . U P A 1
C14A C 0.7205(17) 0.1246(7) 0.0448(8) 0.024(2) Uani 0.6 1 d . U P A 1
C15A C 0.5619(11) 0.1056(4) 0.0191(5) 0.0272(18) Uani 0.6 1 d . U P A 1
H15A H 0.524325 0.056585 0.023026 0.041 Uiso 0.6 1 calc R U P A 1
C16A C 0.4640(11) 0.1606(5) -0.0117(4) 0.0272(17) Uani 0.6 1 d . U P A 1
H16A H 0.356943 0.149690 -0.031068 0.041 Uiso 0.6 1 calc R U P A 1
C17A C 0.5195(10) 0.2316(4) -0.0150(5) 0.0270(16) Uani 0.6 1 d . U P A 1
H17A H 0.451480 0.270252 -0.035306 0.041 Uiso 0.6 1 calc R U P A 1
C18A C 0.675(3) 0.2450(10) 0.0118(15) 0.035(4) Uani 0.6 1 d . U P A 1
C13B C 0.789(5) 0.1811(17) 0.047(2) 0.019(2) Uani 0.4 1 d . U P B 2
C14B C 0.671(5) 0.2284(15) 0.008(2) 0.026(4) Uani 0.4 1 d . U P B 2
C15B C 0.5112(19) 0.2006(9) -0.0156(8) 0.037(4) Uani 0.4 1 d . U P B 2
H15B H 0.430637 0.232689 -0.038515 0.056 Uiso 0.4 1 calc R U P B 2
C16B C 0.479(2) 0.1285(9) -0.0049(8) 0.039(3) Uani 0.4 1 d . U P B 2
H16B H 0.376273 0.109337 -0.022041 0.058 Uiso 0.4 1 calc R U P B 2
C17B C 0.5961(19) 0.0827(8) 0.0312(8) 0.041(4) Uani 0.4 1 d . U P B 2
H17B H 0.572269 0.032455 0.039359 0.062 Uiso 0.4 1 calc R U P B 2
C18B C 0.746(3) 0.1091(10) 0.0552(12) 0.026(4) Uani 0.4 1 d . U P B 2
B1 B 0.9791(3) 0.21351(15) 0.06933(15) 0.0216(6) Uani 1 1 d . . . . .
N1 N 0.2515(3) 0.05648(13) 0.16157(12) 0.0261(5) Uani 1 1 d . . . . .
C19 C 0.4142(3) 0.08176(15) 0.19143(14) 0.0296(6) Uani 1 1 d . . . . .
H19A H 0.407971 0.123992 0.224109 0.041 Uiso 1 1 calc R U . . .
H19B H 0.467741 0.098982 0.151930 0.041 Uiso 1 1 calc R U . . .
C20 C 0.5105(3) 0.02031(16) 0.23187(15) 0.0345(6) Uani 1 1 d . . . . .
H20A H 0.466044 0.008449 0.275569 0.048 Uiso 1 1 calc R U . . .
H20B H 0.620828 0.037504 0.246946 0.048 Uiso 1 1 calc R U . . .
C21 C 0.5114(3) -0.04942(16) 0.18656(16) 0.0366(7) Uani 1 1 d . . . . .
H21A H 0.570442 -0.039896 0.146738 0.051 Uiso 1 1 calc R U . . .
H21B H 0.565715 -0.089778 0.216325 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3433(3) -0.07287(15) 0.15648(16) 0.0323(6) Uani 1 1 d . . . . .
H22A H 0.346279 -0.115683 0.124145 0.045 Uiso 1 1 calc R U . . .
H22B H 0.288881 -0.088595 0.196212 0.045 Uiso 1 1 calc R U . . .
C23 C 0.2511(3) -0.01056(14) 0.11564(15) 0.0300(6) Uani 1 1 d . . . . .
H23A H 0.298943 0.001683 0.072927 0.042 Uiso 1 1 calc R U . . .
H23B H 0.140596 -0.026661 0.099092 0.042 Uiso 1 1 calc R U . . .
N2 N 0.4230(3) 0.52625(15) 0.22789(13) 0.0359(6) Uani 1 1 d . . . . .
C24 C 0.4955(4) 0.45226(18) 0.22958(16) 0.0417(7) Uani 1 1 d . . . . .
H24A H 0.410645 0.414578 0.225605 0.058 Uiso 1 1 calc R U . . .
H24B H 0.564776 0.445314 0.276426 0.058 Uiso 1 1 calc R U . . .
C25 C 0.5928(4) 0.43938(19) 0.17024(17) 0.0419(7) Uani 1 1 d . . . . .
H25A H 0.687529 0.471616 0.178005 0.059 Uiso 1 1 calc R U . . .
H25B H 0.628996 0.387341 0.171522 0.059 Uiso 1 1 calc R U . . .
C26 C 0.4947(4) 0.4560(2) 0.09760(17) 0.0473(8) Uani 1 1 d . . . . .
H26A H 0.409862 0.418532 0.086599 0.066 Uiso 1 1 calc R U . . .
H26B H 0.562991 0.452790 0.060307 0.066 Uiso 1 1 calc R U . . .
C27 C 0.4210(4) 0.5325(2) 0.09600(17) 0.0478(8) Uani 1 1 d . . . . .
H27A H 0.349286 0.539883 0.049851 0.067 Uiso 1 1 calc R U . . .
H27B H 0.505309 0.570485 0.099898 0.067 Uiso 1 1 calc R U . . .
C28 C 0.3282(4) 0.54161(17) 0.15743(16) 0.0389(7) Uani 1 1 d . . . . .
H28A H 0.287298 0.592839 0.157092 0.054 Uiso 1 1 calc R U . . .
H28B H 0.235966 0.507802 0.149705 0.054 Uiso 1 1 calc R U . . .
H1NA H 0.199(4) 0.0458(18) 0.1971(18) 0.039(9) Uiso 1 1 d . . . . .
H1NB H 0.201(4) 0.0890(19) 0.1359(18) 0.039(9) Uiso 1 1 d . . . . .
H2N H 0.487(4) 0.556(2) 0.2331(18) 0.037(10) 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
Cl2 C6 1.752(3) . ?
Cl3 C8 1.773(3) . ?
Cl1 C2 1.752(3) . ?
Cl4 C12 1.751(3) . ?
Cl5A C14A 1.868(13) . ?
F1A C18A 1.44(2) . ?
F1B C18B 1.47(2) . ?
Cl5B C14B 1.58(3) . ?
O1 B1 1.495(3) . ?
O1 H1O 0.8350 . ?
C1 C2 1.402(4) . ?
C1 C6 1.408(4) . ?
C1 B1 1.667(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.399(4) . ?
C7 C12 1.409(4) . ?
C7 B1 1.672(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.381(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C13A C18A 1.40(3) . ?
C13A C14A 1.41(2) . ?
C13A B1 1.64(3) . ?
C14A C15A 1.407(18) . ?
C15A C16A 1.368(10) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.373(10) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.36(3) . ?
C17A H17A 0.9500 . ?
C13B C18B 1.37(4) . ?
C13B C14B 1.42(5) . ?
C13B B1 1.72(4) . ?
C14B C15B 1.46(4) . ?
C15B C16B 1.354(17) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.391(18) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.37(3) . ?
C17B H17B 0.9500 . ?
N1 C19 1.486(4) . ?
N1 C23 1.492(3) . ?
N1 H1NA 0.89(3) . ?
N1 H1NB 0.84(4) . ?
C19 C20 1.514(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.526(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.513(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
N2 C28 1.469(4) . ?
N2 C24 1.473(4) . ?
N2 H2N 0.76(4) . ?
C24 C25 1.523(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.518(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.520(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.522(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
B1 O1 H1O 111.9 . . ?
C2 C1 C6 111.6(2) . . ?
C2 C1 B1 128.8(2) . . ?
C6 C1 B1 119.0(2) . . ?
C3 C2 C1 124.9(2) . . ?
C3 C2 Cl1 112.9(2) . . ?
C1 C2 Cl1 122.09(19) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 125.4(2) . . ?
C5 C6 Cl2 113.6(2) . . ?
C1 C6 Cl2 120.92(19) . . ?
C8 C7 C12 110.9(2) . . ?
C8 C7 B1 122.5(2) . . ?
C12 C7 B1 126.6(2) . . ?
C9 C8 C7 126.3(3) . . ?
C9 C8 Cl3 112.9(2) . . ?
C7 C8 Cl3 120.8(2) . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 125.5(3) . . ?
C11 C12 Cl4 114.1(2) . . ?
C7 C12 Cl4 120.3(2) . . ?
C18A C13A C14A 108(2) . . ?
C18A C13A B1 126.2(16) . . ?
C14A C13A B1 125.3(16) . . ?
C15A C14A C13A 127.0(14) . . ?
C15A C14A Cl5A 111.8(9) . . ?
C13A C14A Cl5A 121.0(14) . . ?
C16A C15A C14A 117.2(8) . . ?
C16A C15A H15A 121.4 . . ?
C14A C15A H15A 121.4 . . ?
C15A C16A C17A 120.5(8) . . ?
C15A C16A H16A 119.8 . . ?
C17A C16A H16A 119.8 . . ?
C18A C17A C16A 118.2(11) . . ?
C18A C17A H17A 120.9 . . ?
C16A C17A H17A 120.9 . . ?
C17A C18A C13A 128.4(18) . . ?
C17A C18A F1A 114.7(17) . . ?
C13A C18A F1A 117(2) . . ?
C18B C13B C14B 117(3) . . ?
C18B C13B B1 124(3) . . ?
C14B C13B B1 119(2) . . ?
C13B C14B C15B 120(3) . . ?
C13B C14B Cl5B 124(3) . . ?
C15B C14B Cl5B 115(2) . . ?
C16B C15B C14B 119.3(17) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
C15B C16B C17B 119.8(14) . . ?
C15B C16B H16B 120.1 . . ?
C17B C16B H16B 120.1 . . ?
C18B C17B C16B 120.9(14) . . ?
C18B C17B H17B 119.5 . . ?
C16B C17B H17B 119.5 . . ?
C13B C18B C17B 123(2) . . ?
C13B C18B F1B 122(2) . . ?
C17B C18B F1B 114.7(15) . . ?
O1 B1 C13A 112.6(8) . . ?
O1 B1 C1 100.12(19) . . ?
C13A B1 C1 116.2(9) . . ?
O1 B1 C7 108.25(19) . . ?
C13A B1 C7 105.3(7) . . ?
C1 B1 C7 114.4(2) . . ?
O1 B1 C13B 106.0(12) . . ?
C1 B1 C13B 113.1(14) . . ?
C7 B1 C13B 113.5(11) . . ?
C19 N1 C23 112.5(2) . . ?
C19 N1 H1NA 110(2) . . ?
C23 N1 H1NA 108(2) . . ?
C19 N1 H1NB 112(2) . . ?
C23 N1 H1NB 106(2) . . ?
H1NA N1 H1NB 108(3) . . ?
N1 C19 C20 111.4(2) . . ?
N1 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
N1 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 112.0(2) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 110.5(2) . . ?
C22 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C21 111.4(2) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
N1 C23 C22 110.9(2) . . ?
N1 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.0 . . ?
C28 N2 C24 111.0(2) . . ?
C28 N2 H2N 105(3) . . ?
C24 N2 H2N 110(3) . . ?
N2 C24 C25 113.8(3) . . ?
N2 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
N2 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C26 C25 C24 110.5(3) . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 C27 111.4(3) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 C28 110.5(3) . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
N2 C28 C27 113.2(3) . . ?
N2 C28 H28A 108.9 . . ?
C27 C28 H28A 108.9 . . ?
N2 C28 H28B 108.9 . . ?
C27 C28 H28B 108.9 . . ?
H28A C28 H28B 107.8 . . ?

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
C6 C1 C2 C3 -3.8(4) . . . . ?
B1 C1 C2 C3 167.2(2) . . . . ?
C6 C1 C2 Cl1 173.87(18) . . . . ?
B1 C1 C2 Cl1 -15.1(4) . . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
Cl1 C2 C3 C4 -176.0(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 Cl2 178.8(2) . . . . ?
C2 C1 C6 C5 2.9(4) . . . . ?
B1 C1 C6 C5 -169.1(2) . . . . ?
C2 C1 C6 Cl2 -175.80(18) . . . . ?
B1 C1 C6 Cl2 12.2(3) . . . . ?
C12 C7 C8 C9 3.5(4) . . . . ?
B1 C7 C8 C9 -174.5(2) . . . . ?
C12 C7 C8 Cl3 -174.04(18) . . . . ?
B1 C7 C8 Cl3 8.0(3) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
Cl3 C8 C9 C10 177.1(2) . . . . ?
C8 C9 C10 C11 -2.1(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 C7 2.1(4) . . . . ?
C10 C11 C12 Cl4 -174.5(2) . . . . ?
C8 C7 C12 C11 -4.2(4) . . . . ?
B1 C7 C12 C11 173.6(3) . . . . ?
C8 C7 C12 Cl4 172.12(19) . . . . ?
B1 C7 C12 Cl4 -10.0(4) . . . . ?
C18A C13A C14A C15A 5(3) . . . . ?
B1 C13A C14A C15A -178.0(14) . . . . ?
C18A C13A C14A Cl5A -169.6(17) . . . . ?
B1 C13A C14A Cl5A 8(3) . . . . ?
C13A C14A C15A C16A -2(2) . . . . ?
Cl5A C14A C15A C16A 173.2(8) . . . . ?
C14A C15A C16A C17A -1.9(15) . . . . ?
C15A C16A C17A C18A 1.5(19) . . . . ?
C16A C17A C18A C13A 3(4) . . . . ?
C16A C17A C18A F1A -170.4(14) . . . . ?
C14A C13A C18A C17A -5(4) . . . . ?
B1 C13A C18A C17A 177(2) . . . . ?
C14A C13A C18A F1A 167(2) . . . . ?
B1 C13A C18A F1A -10(4) . . . . ?
C18B C13B C14B C15B 3(5) . . . . ?
B1 C13B C14B C15B 176(3) . . . . ?
C18B C13B C14B Cl5B 175(3) . . . . ?
B1 C13B C14B Cl5B -12(5) . . . . ?
C13B C14B C15B C16B -4(4) . . . . ?
Cl5B C14B C15B C16B -176.0(18) . . . . ?
C14B C15B C16B C17B 2(3) . . . . ?
C15B C16B C17B C18B -1(3) . . . . ?
C14B C13B C18B C17B -2(5) . . . . ?
B1 C13B C18B C17B -174(2) . . . . ?
C14B C13B C18B F1B -177(3) . . . . ?
B1 C13B C18B F1B 10(5) . . . . ?
C16B C17B C18B C13B 1(4) . . . . ?
C16B C17B C18B F1B 176.7(15) . . . . ?
C18A C13A B1 O1 -152(2) . . . . ?
C14A C13A B1 O1 31(2) . . . . ?
C18A C13A B1 C1 93(2) . . . . ?
C14A C13A B1 C1 -84(2) . . . . ?
C18A C13A B1 C7 -35(3) . . . . ?
C14A C13A B1 C7 148.7(19) . . . . ?
C2 C1 B1 O1 -115.1(3) . . . . ?
C6 C1 B1 O1 55.3(3) . . . . ?
C2 C1 B1 C13A 6.3(8) . . . . ?
C6 C1 B1 C13A 176.8(7) . . . . ?
C2 C1 B1 C7 129.4(3) . . . . ?
C6 C1 B1 C7 -60.2(3) . . . . ?
C2 C1 B1 C13B -2.7(13) . . . . ?
C6 C1 B1 C13B 167.7(12) . . . . ?
C8 C7 B1 O1 42.5(3) . . . . ?
C12 C7 B1 O1 -135.1(2) . . . . ?
C8 C7 B1 C13A -78.1(10) . . . . ?
C12 C7 B1 C13A 104.3(10) . . . . ?
C8 C7 B1 C1 153.2(2) . . . . ?
C12 C7 B1 C1 -24.4(3) . . . . ?
C8 C7 B1 C13B -74.9(15) . . . . ?
C12 C7 B1 C13B 107.5(15) . . . . ?
C18B C13B B1 O1 27(4) . . . . ?
C14B C13B B1 O1 -145(3) . . . . ?
C18B C13B B1 C1 -82(3) . . . . ?
C14B C13B B1 C1 106(3) . . . . ?
C18B C13B B1 C7 146(3) . . . . ?
C14B C13B B1 C7 -26(4) . . . . ?
C23 N1 C19 C20 -55.0(3) . . . . ?
N1 C19 C20 C21 53.5(3) . . . . ?
C19 C20 C21 C22 -53.3(3) . . . . ?
C20 C21 C22 C23 54.5(3) . . . . ?
C19 N1 C23 C22 56.3(3) . . . . ?
C21 C22 C23 N1 -55.9(3) . . . . ?
C28 N2 C24 C25 54.3(3) . . . . ?
N2 C24 C25 C26 -53.6(4) . . . . ?
C24 C25 C26 C27 52.7(4) . . . . ?
C25 C26 C27 C28 -53.5(4) . . . . ?
C24 N2 C28 C27 -54.8(3) . . . . ?
C26 C27 C28 N2 55.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O Cl3 0.83 2.32 2.9569(18) 133 . yes
N1 H1NB O1 0.84(4) 1.89(4) 2.714(3) 169(3) 1_455 yes
N1 H1NA N2 0.89(3) 1.93(4) 2.819(3) 177(3) 2_545 yes

_refine_diff_density_max         0.667
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.066



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: piperidine'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2004800'
loop_
_audit_author_name
_audit_author_address
'Tamas Holczbauer'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2024-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(2-chloro-6-fluorophenyl)bis(2,6-dichlorophenyl)(hydroxy)borate + piperidin-1-ium, +2 piperidine'
_chemical_name_common            
'asymmetrically halogenated triaryl borane structure hydridecomplex'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C18 H9 B Cl5 F, O H2, 3(C5 H11 N)
;
_chemical_formula_sum            'C29 H31 B Cl5 F N2.20 O'
_chemical_formula_weight         633.42

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'
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'
O O 0.0106 0.0060 '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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   10.208(2)
_cell_length_b                   17.008(3)
_cell_length_c                   20.085(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.581(6)
_cell_angle_gamma                90
_cell_volume                     3485.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    10248
_cell_measurement_theta_min      3.045
_cell_measurement_theta_max      21.85

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             1310
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.445
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.971643
_exptl_absorpt_correction_T_max  0.996687
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_radiation_detector       RX
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14920
_diffrn_reflns_av_unetI/netI     0.1662
_diffrn_reflns_av_R_equivalents  0.1706
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_max         21.897
_diffrn_reflns_theta_full        21.897
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4200
_reflns_number_gt                2303
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
# Spek, A. L. (2009). Acta Cryst. D65, 148--155. 
_refine_special_details          
'Refined as a 2-component perfect inversion 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)+(0.1786P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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 a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4200
_refine_ls_number_parameters     271
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.1116
_refine_ls_wR_factor_ref         0.3163
_refine_ls_wR_factor_gt          0.2789
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was stable under a N2-piperidine atmosphere in an 
ampoule in glove box. Fastly decomposed during the preparation on the air.
High resolution data was lost, and 
disordered region is appeared in the crystal lattices. So
the high resolution data was cut during the refinement.
;
_vrf_PLAT234_shelx               
;
PROBLEM: Large Hirshfeld Difference C1 --C6 . 0.26 Ang.
RESPONSE: The crystal was stable under a N2-piperidine atmosphere in an 
ampoule in glove box. Fastly decomposed during the preparation on the air.
High resolution data was lost, and 
disordered region is appeared in the crystal lattices. So
the high resolution data was cut during the refinement.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.025 Ang.
RESPONSE: The crystal was stable under a N2-piperidine atmosphere in an 
ampoule in glove box. Fastly decomposed during the preparation on the air.
High resolution data was lost, and 
disordered region is appeared in the crystal lattices. So
the high resolution data was cut during the refinement.
;
_vrf_PLAT430_shelx               
;
PROBLEM: Short Inter D...A Contact O1 ..N1 . 2.73 Ang.
RESPONSE: The crystal was stable under a N2-piperidine atmosphere in an 
ampoule in glove box. Fastly decomposed during the preparation on the air.
High resolution data was lost, and 
disordered region is appeared in the crystal lattices. So
the high resolution data was cut during the refinement.
;
# end Validation Reply Form


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 0.6278(6) 0.9518(3) 0.6850(3) 0.0653(17) Uani 1 1 d . . . . .
Cl2 Cl 0.2830(6) 0.8573(4) 0.8730(3) 0.0679(18) Uani 1 1 d . . . . .
Cl3 Cl 0.6455(6) 0.6701(4) 0.8786(3) 0.074(2) Uani 1 1 d . . . . .
Cl4 Cl 0.3347(6) 0.8063(4) 0.6857(4) 0.082(2) Uani 1 1 d . . . . .
Cl5 Cl 0.6732(6) 0.7270(4) 0.6807(4) 0.080(2) Uani 1 1 d . . . . .
F6 F 0.7678(11) 0.9381(6) 0.8622(6) 0.053(3) Uani 1 1 d . . . . .
O1 O 0.5652(13) 0.8335(8) 0.8815(7) 0.053(4) Uani 1 1 d . . . . .
C1 C 0.4808(13) 0.7412(7) 0.7889(8) 0.057(6) Uani 1 1 d G U . . .
C2 C 0.5157(13) 0.6759(9) 0.8270(7) 0.063(7) Uani 1 1 d G U . . .
C3 C 0.4475(18) 0.6057(8) 0.8187(9) 0.087(9) Uani 1 1 d G U . . .
H3 H 0.470843 0.561997 0.844145 0.121 Uiso 1 1 calc R U . . .
C4 C 0.3442(17) 0.6008(8) 0.7722(10) 0.082(9) Uani 1 1 d G U . . .
H4 H 0.298542 0.553882 0.766679 0.115 Uiso 1 1 calc R U . . .
C5 C 0.3093(15) 0.6662(10) 0.7341(8) 0.077(8) Uani 1 1 d G U . . .
H5 H 0.240213 0.662903 0.703082 0.108 Uiso 1 1 calc R U . . .
C6 C 0.3776(15) 0.7363(8) 0.7424(7) 0.051(6) Uani 1 1 d G U . . .
C7 C 0.4661(14) 0.9099(8) 0.7870(8) 0.062(6) Uani 1 1 d G U . . .
C8 C 0.3541(15) 0.9232(9) 0.8232(8) 0.063(7) Uani 1 1 d G U . . .
C9 C 0.2818(13) 0.9916(10) 0.8130(9) 0.069(7) Uani 1 1 d G U . . .
H9 H 0.206896 1.000504 0.837273 0.096 Uiso 1 1 calc R U . . .
C10 C 0.3214(17) 1.0467(8) 0.7666(9) 0.086(9) Uani 1 1 d G U . . .
H10 H 0.272976 1.092468 0.759773 0.120 Uiso 1 1 calc R U . . .
C11 C 0.4333(17) 1.0334(8) 0.7304(8) 0.080(8) Uani 1 1 d G U . . .
H11 H 0.459799 1.070280 0.699303 0.112 Uiso 1 1 calc R U . . .
C12 C 0.5057(13) 0.9650(9) 0.7406(8) 0.060(6) Uani 1 1 d G U . . .
C13 C 0.7157(10) 0.8290(10) 0.7825(8) 0.066(7) Uani 1 1 d G U . . .
C14 C 0.7639(16) 0.7773(9) 0.7355(8) 0.069(8) Uani 1 1 d G U . . .
C15 C 0.8982(17) 0.7707(10) 0.7274(9) 0.091(9) Uani 1 1 d G U . . .
H15 H 0.930450 0.736064 0.695902 0.128 Uiso 1 1 calc R U . . .
C16 C 0.9844(11) 0.8157(12) 0.7662(11) 0.088(9) Uani 1 1 d G U . . .
H16 H 1.074255 0.811305 0.760728 0.123 Uiso 1 1 calc R U . . .
C17 C 0.9362(14) 0.8674(11) 0.8132(10) 0.084(9) Uani 1 1 d G U . . .
H17 H 0.993869 0.897599 0.839191 0.117 Uiso 1 1 calc R U . . .
C18 C 0.8019(15) 0.8741(10) 0.8214(8) 0.068(7) Uani 1 1 d G U . . .
B1 B 0.558(2) 0.8264(15) 0.8087(12) 0.047(7) Uani 1 1 d . . . . .
N1 N 0.580(2) 0.9453(12) 0.9789(11) 0.076(6) Uiso 1 1 d . . . . .
C19 C 0.457(3) 0.9314(18) 1.0184(17) 0.100(10) Uiso 1 1 d . . . . .
H19A H 0.455506 0.966887 1.056229 0.140 Uiso 1 1 calc R U . . .
H19B H 0.379379 0.941477 0.990576 0.140 Uiso 1 1 calc R U . . .
C20 C 0.456(3) 0.8498(17) 1.0417(17) 0.097(9) Uiso 1 1 d . . . . .
H20A H 0.442723 0.815333 1.003586 0.136 Uiso 1 1 calc R U . . .
H20B H 0.382622 0.842502 1.070724 0.136 Uiso 1 1 calc R U . . .
C21 C 0.581(2) 0.8258(15) 1.0789(13) 0.072(7) Uiso 1 1 d . . . . .
H21A H 0.582512 0.849127 1.122936 0.100 Uiso 1 1 calc R U . . .
H21B H 0.582490 0.769094 1.084100 0.100 Uiso 1 1 calc R U . . .
C22 C 0.699(3) 0.8509(16) 1.0433(15) 0.084(8) Uiso 1 1 d . . . . .
H22A H 0.775019 0.845585 1.073259 0.118 Uiso 1 1 calc R U . . .
H22B H 0.711748 0.815785 1.006004 0.118 Uiso 1 1 calc R U . . .
C23 C 0.694(3) 0.9299(16) 1.0191(15) 0.084(8) Uiso 1 1 d . . . . .
H23A H 0.771216 0.939843 0.993070 0.117 Uiso 1 1 calc R U . . .
H23B H 0.696631 0.965740 1.056638 0.117 Uiso 1 1 calc R U . . .
N2 N 0.640(4) 1.102(3) 0.912(3) 0.139(18) Uiso 0.6 1 d D . P . .
C24 C 0.731(3) 1.151(2) 0.951(2) 0.077(13) Uiso 0.6 1 d D . P . .
H24A H 0.752463 1.197097 0.925718 0.108 Uiso 0.6 1 calc R U P . .
H24B H 0.810858 1.121695 0.960321 0.108 Uiso 0.6 1 calc R U P . .
C25 C 0.674(4) 1.176(3) 1.016(2) 0.117(19) Uiso 0.6 1 d D . P . .
H25A H 0.654864 1.129489 1.042258 0.164 Uiso 0.6 1 calc R U P . .
H25B H 0.737044 1.207402 1.040608 0.164 Uiso 0.6 1 calc R U P . .
C26 C 0.552(4) 1.221(3) 1.005(3) 0.19(3) Uiso 0.6 1 d D . P . .
H26A H 0.570048 1.266830 0.977563 0.272 Uiso 0.6 1 calc R U P . .
H26B H 0.521343 1.239957 1.047441 0.272 Uiso 0.6 1 calc R U P . .
C27 C 0.447(4) 1.172(3) 0.971(2) 0.093(15) Uiso 0.6 1 d D . P . .
H27A H 0.407810 1.138325 1.004109 0.122 Uiso 0.6 1 calc R U P . .
H27B H 0.379630 1.206267 0.952791 0.122 Uiso 0.6 1 calc R U P . .
C28 C 0.502(4) 1.123(5) 0.918(4) 0.23(4) Uiso 0.6 1 d D . P . .
H28A H 0.454115 1.074215 0.917930 0.294 Uiso 0.6 1 calc R U P . .
H28B H 0.477803 1.149398 0.876160 0.294 Uiso 0.6 1 calc R U P . .
C29 C 0.993(5) 1.025(3) 1.144(3) 0.089(14) Uiso 0.6 1 d . . P . .
H29A H 1.070637 1.039414 1.170331 0.125 Uiso 0.6 1 calc R U P . .
H29B H 0.921030 1.021812 1.174939 0.125 Uiso 0.6 1 calc R U P . .
C30 C 0.965(5) 1.085(3) 1.099(3) 0.100(16) Uiso 0.6 1 d . . P . .
H30A H 0.954790 1.134084 1.123347 0.140 Uiso 0.6 1 calc R U P . .
H30B H 0.883081 1.074006 1.075666 0.140 Uiso 0.6 1 calc R U P . .
C31 C 1.079(7) 1.096(4) 1.046(4) 0.14(2) Uiso 0.6 1 d . . P . .
H31A H 1.053706 1.134972 1.012371 0.195 Uiso 0.6 1 calc R U P . .
H31B H 1.160415 1.112213 1.067440 0.195 Uiso 0.6 1 calc R U P . .
C32 C 1.092(5) 1.013(3) 1.014(3) 0.101(16) Uiso 0.6 1 d . . P . .
H32A H 1.015924 1.003841 0.984691 0.141 Uiso 0.6 1 calc R U P . .
H32B H 1.168302 1.013114 0.985904 0.141 Uiso 0.6 1 calc R U P . .
C33 C 1.105(6) 0.942(3) 1.063(3) 0.099(16) Uiso 0.6 1 d . . P . .
H33A H 1.083215 0.893589 1.039863 0.138 Uiso 0.6 1 calc R U P . .
H33B H 1.194660 0.938350 1.080008 0.138 Uiso 0.6 1 calc R U P . .
N3 N 1.011(5) 0.955(3) 1.121(3) 0.123(16) Uiso 0.6 1 d . . 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
Cl1 C12 1.712(13) . ?
Cl2 C8 1.681(14) . ?
Cl3 C2 1.663(14) . ?
Cl4 C6 1.696(14) . ?
Cl5 C14 1.657(15) . ?
F6 C18 1.413(17) . ?
O1 B1 1.47(3) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 B1 1.69(3) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 B1 1.75(3) . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 B1 1.71(3) . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
N1 C23 1.43(3) . ?
N1 C19 1.52(4) . ?
C19 C20 1.46(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.52(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.48(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.43(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
N2 C24 1.46(3) . ?
N2 C28 1.46(3) . ?
C24 C25 1.50(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.47(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.50(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.49(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 N3 1.29(6) . ?
C29 C30 1.40(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.61(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.56(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.56(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 N3 1.54(7) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

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 120.0 . . ?
C2 C1 B1 116.3(12) . . ?
C6 C1 B1 123.3(12) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 Cl3 125.4(10) . . ?
C3 C2 Cl3 114.4(10) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 Cl4 113.7(10) . . ?
C1 C6 Cl4 125.9(10) . . ?
C8 C7 C12 120.0 . . ?
C8 C7 B1 116.4(13) . . ?
C12 C7 B1 123.4(13) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 Cl2 114.2(9) . . ?
C7 C8 Cl2 125.3(9) . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 Cl1 114.0(10) . . ?
C7 C12 Cl1 125.4(10) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 B1 123.2(13) . . ?
C18 C13 B1 115.3(13) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 Cl5 114.5(11) . . ?
C13 C14 Cl5 125.2(11) . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 F6 113.0(12) . . ?
C13 C18 F6 126.1(12) . . ?
O1 B1 C1 108.4(18) . . ?
O1 B1 C13 106.5(15) . . ?
C1 B1 C13 112.7(15) . . ?
O1 B1 C7 101.1(16) . . ?
C1 B1 C7 113.1(14) . . ?
C13 B1 C7 114.0(17) . . ?
C23 N1 C19 111(2) . . ?
C20 C19 N1 109(3) . . ?
C20 C19 H19A 109.9 . . ?
N1 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
N1 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 C21 114(3) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 112(2) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 114(2) . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 N1 113(2) . . ?
C22 C23 H23A 109.0 . . ?
N1 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
N1 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C24 N2 C28 114(3) . . ?
N2 C24 C25 112(3) . . ?
N2 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
N2 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C26 C25 C24 112(3) . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 111(3) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C28 C27 C26 111(2) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
N2 C28 C27 125(3) . . ?
N2 C28 H28A 105.9 . . ?
C27 C28 H28A 105.9 . . ?
N2 C28 H28B 106.0 . . ?
C27 C28 H28B 106.0 . . ?
H28A C28 H28B 106.3 . . ?
N3 C29 C30 118(5) . . ?
N3 C29 H29A 107.9 . . ?
C30 C29 H29A 107.9 . . ?
N3 C29 H29B 107.9 . . ?
C30 C29 H29B 107.9 . . ?
H29A C29 H29B 107.2 . . ?
C29 C30 C31 112(5) . . ?
C29 C30 H30A 109.1 . . ?
C31 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
C31 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C30 104(5) . . ?
C32 C31 H31A 110.9 . . ?
C30 C31 H31A 111.0 . . ?
C32 C31 H31B 111.0 . . ?
C30 C31 H31B 110.9 . . ?
H31A C31 H31B 109.0 . . ?
C33 C32 C31 116(5) . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32B 108.2 . . ?
C31 C32 H32B 108.2 . . ?
H32A C32 H32B 107.3 . . ?
N3 C33 C32 109(4) . . ?
N3 C33 H33A 109.9 . . ?
C32 C33 H33A 109.9 . . ?
N3 C33 H33B 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
C29 N3 C33 121(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
C6 C1 C2 C3 0.0 . . . . ?
B1 C1 C2 C3 173.2(14) . . . . ?
C6 C1 C2 Cl3 173.5(14) . . . . ?
B1 C1 C2 Cl3 -13.3(15) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
Cl3 C2 C3 C4 -174.2(12) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 Cl4 172.9(12) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
B1 C1 C6 C5 -172.7(15) . . . . ?
C2 C1 C6 Cl4 -172.0(13) . . . . ?
B1 C1 C6 Cl4 15.3(18) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
B1 C7 C8 C9 174.5(15) . . . . ?
C12 C7 C8 Cl2 171.2(14) . . . . ?
B1 C7 C8 Cl2 -14.3(15) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
Cl2 C8 C9 C10 -172.1(13) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C10 C11 C12 Cl1 172.1(12) . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
B1 C7 C12 C11 -174.1(16) . . . . ?
C8 C7 C12 Cl1 -171.2(13) . . . . ?
B1 C7 C12 Cl1 14.7(17) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
B1 C13 C14 C15 -165.6(17) . . . . ?
C18 C13 C14 Cl5 -173.3(14) . . . . ?
B1 C13 C14 Cl5 21.1(18) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
Cl5 C14 C15 C16 174.0(13) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C16 C17 C18 F6 -169.6(15) . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
B1 C13 C18 C17 166.6(16) . . . . ?
C14 C13 C18 F6 168.2(17) . . . . ?
B1 C13 C18 F6 -25.2(17) . . . . ?
C2 C1 B1 O1 -42.4(18) . . . . ?
C6 C1 B1 O1 130.6(14) . . . . ?
C2 C1 B1 C13 75.2(17) . . . . ?
C6 C1 B1 C13 -111.8(15) . . . . ?
C2 C1 B1 C7 -153.7(13) . . . . ?
C6 C1 B1 C7 19(2) . . . . ?
C14 C13 B1 O1 134.8(14) . . . . ?
C18 C13 B1 O1 -31(2) . . . . ?
C14 C13 B1 C1 16(2) . . . . ?
C18 C13 B1 C1 -150.1(13) . . . . ?
C14 C13 B1 C7 -114.6(17) . . . . ?
C18 C13 B1 C7 79.2(17) . . . . ?
C8 C7 B1 O1 -46.8(18) . . . . ?
C12 C7 B1 O1 127.6(14) . . . . ?
C8 C7 B1 C1 68.9(18) . . . . ?
C12 C7 B1 C1 -116.7(15) . . . . ?
C8 C7 B1 C13 -160.6(12) . . . . ?
C12 C7 B1 C13 14(2) . . . . ?
C23 N1 C19 C20 -59(3) . . . . ?
N1 C19 C20 C21 53(3) . . . . ?
C19 C20 C21 C22 -46(4) . . . . ?
C20 C21 C22 C23 45(3) . . . . ?
C21 C22 C23 N1 -53(4) . . . . ?
C19 N1 C23 C22 60(3) . . . . ?
C28 N2 C24 C25 35(7) . . . . ?
N2 C24 C25 C26 -60(5) . . . . ?
C24 C25 C26 C27 63(5) . . . . ?
C25 C26 C27 C28 -42(7) . . . . ?
C24 N2 C28 C27 -18(12) . . . . ?
C26 C27 C28 N2 21(11) . . . . ?
N3 C29 C30 C31 -58(7) . . . . ?
C29 C30 C31 C32 55(6) . . . . ?
C30 C31 C32 C33 -49(6) . . . . ?
C31 C32 C33 N3 40(6) . . . . ?
C30 C29 N3 C33 49(8) . . . . ?
C32 C33 N3 C29 -37(7) . . . . ?

_refine_diff_density_max         0.705
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.102



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: piperidine'
