# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_3OTf
_database_code_depnum_ccdc_archive 'CCDC 1448866'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            DAC-BCl-N(iPr)2-OTf
_chemical_melting_point          ?
_chemical_formula_moiety         {(C24H28N2O2)-B-Cl-N(C3H7)2-SO3CF3-CH2Cl2
_chemical_formula_sum            'C32 H44 B Cl3 F3 N3 O5 S'
_chemical_formula_weight         756.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   13.8269(7)
_cell_length_b                   17.9052(9)
_cell_length_c                   15.9013(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.190(8)
_cell_angle_gamma                90
_cell_volume                     3760.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27438
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.356
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31927
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             6614
_reflns_number_gt                5112
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0541P)²+3.3632P] 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         6614
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
S1 S 0.79286(6) 0.13740(4) 0.59750(5) 0.0369(2) Uani 1 1 d . . . . .
Cl1 Cl 1.05722(6) 0.34580(5) 0.55538(5) 0.0448(2) Uani 1 1 d . . . . .
N1 N 1.00142(16) 0.31257(13) 0.76089(14) 0.0275(5) Uani 1 1 d . . . . .
O1 O 0.88096(15) 0.27634(13) 0.82402(13) 0.0425(5) Uani 1 1 d . . . . .
B1 B 1.1197(2) 0.35539(18) 0.6699(2) 0.0298(7) Uani 1 1 d . . . . .
C1 C 1.07817(19) 0.29497(15) 0.72871(16) 0.0258(6) Uani 1 1 d . . . . .
F1 F 0.8870(2) 0.01142(13) 0.59435(19) 0.0885(8) Uani 1 1 d . . . . .
N2 N 1.11708(16) 0.22578(12) 0.73887(14) 0.0270(5) Uani 1 1 d . . . . .
O2 O 1.11209(16) 0.10513(12) 0.78213(14) 0.0446(5) Uani 1 1 d . . . . .
F2 F 0.7274(2) -0.00035(13) 0.56142(15) 0.0826(8) Uani 1 1 d . . . . .
C2 C 0.9583(2) 0.26024(17) 0.80914(17) 0.0316(6) Uani 1 1 d . . . . .
Cl2 Cl 0.07529(10) 0.12032(9) 0.14148(9) 0.1081(5) Uani 1 1 d . . . . .
N3 N 1.19342(17) 0.40746(13) 0.70216(14) 0.0324(5) Uani 1 1 d . . . . .
F3 F 0.81300(19) 0.01677(12) 0.69494(13) 0.0723(7) Uani 1 1 d . . . . .
C3 C 1.0226(2) 0.19326(16) 0.84568(18) 0.0316(6) Uani 1 1 d . . . . .
O3 O 0.69985(18) 0.15441(15) 0.61531(17) 0.0607(7) Uani 1 1 d . . . . .
Cl3 Cl 0.11555(10) 0.18018(8) 0.31827(8) 0.0893(4) Uani 1 1 d . . . . .
C4 C 1.0833(2) 0.16715(17) 0.78610(17) 0.0313(6) Uani 1 1 d . . . . .
O4 O 0.79201(17) 0.14781(13) 0.50792(14) 0.0493(6) Uani 1 1 d . . . . .
O5 O 0.88258(17) 0.16485(13) 0.66208(14) 0.0477(6) Uani 1 1 d . . . . .
C5 C 0.9600(2) 0.12989(19) 0.8669(2) 0.0439(8) Uani 1 1 d . . . . .
H5B H 1.0033 0.0882 0.8900 0.066 Uiso 1 1 calc R U . . .
H5C H 0.9284 0.1465 0.9097 0.066 Uiso 1 1 calc R U . . .
H5D H 0.9089 0.1150 0.8142 0.066 Uiso 1 1 calc R U . . .
C6 C 1.1024(2) 0.22044(19) 0.93189(18) 0.0410(7) Uani 1 1 d . . . . .
H6A H 1.1458 0.1796 0.9582 0.061 Uiso 1 1 calc R U . . .
H6B H 1.1422 0.2599 0.9181 0.061 Uiso 1 1 calc R U . . .
H6C H 1.0682 0.2385 0.9723 0.061 Uiso 1 1 calc R U . . .
C11 C 0.9534(2) 0.38622(16) 0.74236(17) 0.0294(6) Uani 1 1 d . . . . .
C12 C 0.9755(2) 0.43972(17) 0.80957(18) 0.0351(7) Uani 1 1 d . . . . .
C13 C 0.9341(2) 0.51022(18) 0.7887(2) 0.0438(8) Uani 1 1 d . . . . .
H13A H 0.9487 0.5470 0.8320 0.053 Uiso 1 1 calc R U . . .
C14 C 0.8715(2) 0.52791(18) 0.7052(2) 0.0422(8) Uani 1 1 d . . . . .
C15 C 0.8445(2) 0.47143(18) 0.6440(2) 0.0403(7) Uani 1 1 d . . . . .
H15A H 0.7989 0.4819 0.5894 0.048 Uiso 1 1 calc R U . . .
C16 C 0.8829(2) 0.39918(17) 0.66086(18) 0.0328(6) Uani 1 1 d . . . . .
C17 C 0.8403(2) 0.33818(18) 0.59479(19) 0.0418(7) Uani 1 1 d . . . . .
H17A H 0.7932 0.3594 0.5434 0.063 Uiso 1 1 calc R U . . .
H17B H 0.8944 0.3144 0.5785 0.063 Uiso 1 1 calc R U . . .
H17C H 0.8063 0.3019 0.6204 0.063 Uiso 1 1 calc R U . . .
C18 C 1.0373(2) 0.42180(19) 0.90260(18) 0.0442(8) Uani 1 1 d . . . . .
H18A H 1.0601 0.3710 0.9056 0.066 Uiso 1 1 calc R U . . .
H18B H 1.0947 0.4546 0.9200 0.066 Uiso 1 1 calc R U . . .
H18C H 0.9963 0.4285 0.9414 0.066 Uiso 1 1 calc R U . . .
C19 C 0.8329(3) 0.6065(2) 0.6833(3) 0.0603(10) Uani 1 1 d . . . . .
H19A H 0.8595 0.6380 0.7337 0.091 Uiso 1 1 calc R U . . .
H19B H 0.8543 0.6249 0.6350 0.091 Uiso 1 1 calc R U . . .
H19C H 0.7603 0.6066 0.6673 0.091 Uiso 1 1 calc R U . . .
C21 C 1.1959(2) 0.20690(15) 0.69778(18) 0.0292(6) Uani 1 1 d . . . . .
C22 C 1.2966(2) 0.21237(16) 0.74902(19) 0.0337(6) Uani 1 1 d . . . . .
C23 C 1.3700(2) 0.20318(17) 0.7059(2) 0.0409(7) Uani 1 1 d . . . . .
H23A H 1.4379 0.2083 0.7379 0.049 Uiso 1 1 calc R U . . .
C24 C 1.3452(3) 0.18670(19) 0.6167(2) 0.0454(8) Uani 1 1 d . . . . .
C25 C 1.2448(2) 0.17404(18) 0.5717(2) 0.0424(8) Uani 1 1 d . . . . .
H25A H 1.2281 0.1594 0.5131 0.051 Uiso 1 1 calc R U . . .
C26 C 1.1678(2) 0.18233(16) 0.61052(19) 0.0356(7) Uani 1 1 d . . . . .
C27 C 1.0609(2) 0.1610(2) 0.5602(2) 0.0497(8) Uani 1 1 d . . . . .
H27A H 1.0171 0.1700 0.5960 0.075 Uiso 1 1 calc R U . . .
H27B H 1.0388 0.1903 0.5074 0.075 Uiso 1 1 calc R U . . .
H27C H 1.0586 0.1089 0.5451 0.075 Uiso 1 1 calc R U . . .
C28 C 1.3263(2) 0.22369(19) 0.84727(19) 0.0416(7) Uani 1 1 d . . . . .
H28A H 1.2665 0.2290 0.8657 0.062 Uiso 1 1 calc R U . . .
H28B H 1.3645 0.1813 0.8762 0.062 Uiso 1 1 calc R U . . .
H28C H 1.3670 0.2679 0.8625 0.062 Uiso 1 1 calc R U . . .
C29 C 1.4251(3) 0.1813(3) 0.5695(3) 0.0736(13) Uani 1 1 d . . . . .
H29A H 1.4904 0.1916 0.6102 0.110 Uiso 1 1 calc R U . . .
H29B H 1.4249 0.1319 0.5461 0.110 Uiso 1 1 calc R U . . .
H29C H 1.4108 0.2169 0.5224 0.110 Uiso 1 1 calc R U . . .
C30 C 1.2459(2) 0.41811(17) 0.79813(18) 0.0376(7) Uani 1 1 d . . . . .
H30A H 1.2193 0.3808 0.8305 0.045 Uiso 1 1 calc R U . . .
C31 C 1.3600(2) 0.4058(2) 0.8201(2) 0.0520(9) Uani 1 1 d . . . . .
H31A H 1.3911 0.4131 0.8821 0.078 Uiso 1 1 calc R U . . .
H31B H 1.3729 0.3559 0.8044 0.078 Uiso 1 1 calc R U . . .
H31C H 1.3878 0.4408 0.7877 0.078 Uiso 1 1 calc R U . . .
C32 C 1.2245(3) 0.49490(19) 0.8294(2) 0.0519(9) Uani 1 1 d . . . . .
H32A H 1.2591 0.5000 0.8911 0.078 Uiso 1 1 calc R U . . .
H32B H 1.2478 0.5327 0.7972 0.078 Uiso 1 1 calc R U . . .
H32C H 1.1530 0.5005 0.8197 0.078 Uiso 1 1 calc R U . . .
C33 C 1.2298(3) 0.46022(19) 0.6454(2) 0.0490(9) Uani 1 1 d . . . . .
H33A H 1.2816 0.4911 0.6858 0.059 Uiso 1 1 calc R U . . .
C34 C 1.2835(3) 0.4201(3) 0.5871(2) 0.0664(11) Uani 1 1 d . . . . .
H34A H 1.3055 0.4560 0.5519 0.100 Uiso 1 1 calc R U . . .
H34B H 1.3411 0.3935 0.6235 0.100 Uiso 1 1 calc R U . . .
H34C H 1.2376 0.3854 0.5494 0.100 Uiso 1 1 calc R U . . .
C35 C 1.1479(4) 0.5139(2) 0.5958(3) 0.0719(12) Uani 1 1 d . . . . .
H35A H 1.1747 0.5466 0.5604 0.108 Uiso 1 1 calc R U . . .
H35B H 1.0921 0.4862 0.5587 0.108 Uiso 1 1 calc R U . . .
H35C H 1.1252 0.5429 0.6371 0.108 Uiso 1 1 calc R U . . .
C40 C 0.1619(3) 0.1659(3) 0.2288(3) 0.0732(12) Uani 1 1 d . . . . .
H40A H 0.1790 0.2138 0.2085 0.088 Uiso 1 1 calc R U . . .
H40B H 0.2234 0.1364 0.2478 0.088 Uiso 1 1 calc R U . . .
C41 C 0.8055(3) 0.0364(2) 0.6127(2) 0.0504(9) 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
S1 O3 1.429(2) . ?
S1 O4 1.433(2) . ?
S1 O5 1.443(2) . ?
S1 C41 1.826(4) . ?
Cl1 B1 1.779(3) . ?
N1 C1 1.345(3) . ?
N1 C2 1.447(3) . ?
N1 C11 1.466(3) . ?
O1 C2 1.196(3) . ?
B1 N3 1.365(4) . ?
B1 C1 1.640(4) . ?
C1 N2 1.341(3) . ?
F1 C41 1.323(4) . ?
N2 C4 1.446(3) . ?
N2 C21 1.466(3) . ?
O2 C4 1.188(3) . ?
F2 C41 1.321(4) . ?
C2 C3 1.504(4) . ?
Cl2 C40 1.745(4) . ?
N3 C30 1.496(3) . ?
N3 C33 1.493(4) . ?
F3 C41 1.328(4) . ?
C3 C4 1.514(4) . ?
C3 C5 1.524(4) . ?
C3 C6 1.562(4) . ?
Cl3 C40 1.743(4) . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 H5D 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C11 C16 1.392(4) . ?
C11 C12 1.400(4) . ?
C12 C13 1.385(4) . ?
C12 C18 1.508(4) . ?
C13 C14 1.390(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(4) . ?
C14 C19 1.509(5) . ?
C15 C16 1.394(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.509(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.393(4) . ?
C21 C26 1.397(4) . ?
C22 C23 1.393(4) . ?
C22 C28 1.507(4) . ?
C23 C24 1.389(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.380(5) . ?
C24 C29 1.511(4) . ?
C25 C26 1.387(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.508(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C32 1.521(4) . ?
C30 C31 1.528(4) . ?
C30 H30A 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C35 1.516(5) . ?
C33 C34 1.527(5) . ?
C33 H33A 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C40 H40A 0.9700 . ?
C40 H40B 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
O3 S1 O4 115.20(15) . . ?
O3 S1 O5 114.90(16) . . ?
O4 S1 O5 114.58(14) . . ?
O3 S1 C41 103.97(17) . . ?
O4 S1 C41 103.46(15) . . ?
O5 S1 C41 102.39(15) . . ?
C1 N1 C2 123.1(2) . . ?
C1 N1 C11 119.7(2) . . ?
C2 N1 C11 117.1(2) . . ?
N3 B1 C1 125.8(2) . . ?
N3 B1 Cl1 122.2(2) . . ?
C1 B1 Cl1 112.0(2) . . ?
N1 C1 N2 120.3(2) . . ?
N1 C1 B1 120.7(2) . . ?
N2 C1 B1 118.8(2) . . ?
C1 N2 C4 123.6(2) . . ?
C1 N2 C21 118.9(2) . . ?
C4 N2 C21 117.4(2) . . ?
O1 C2 N1 118.8(3) . . ?
O1 C2 C3 125.2(3) . . ?
N1 C2 C3 115.6(2) . . ?
B1 N3 C30 123.6(2) . . ?
B1 N3 C33 123.6(2) . . ?
C30 N3 C33 112.8(2) . . ?
C2 C3 C4 112.2(2) . . ?
C2 C3 C5 111.7(2) . . ?
C4 C3 C5 111.4(3) . . ?
C2 C3 C6 105.9(2) . . ?
C4 C3 C6 105.5(2) . . ?
C5 C3 C6 109.8(2) . . ?
O2 C4 N2 119.1(3) . . ?
O2 C4 C3 125.4(3) . . ?
N2 C4 C3 115.1(2) . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C5 H5D 109.5 . . ?
H5B C5 H5D 109.5 . . ?
H5C C5 H5D 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C16 C11 C12 122.1(3) . . ?
C16 C11 N1 119.2(2) . . ?
C12 C11 N1 118.6(2) . . ?
C13 C12 C11 117.3(3) . . ?
C13 C12 C18 120.2(3) . . ?
C11 C12 C18 122.4(3) . . ?
C12 C13 C14 122.2(3) . . ?
C12 C13 H13A 118.9 . . ?
C14 C13 H13A 118.9 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 C19 121.3(3) . . ?
C13 C14 C19 120.7(3) . . ?
C14 C15 C16 122.6(3) . . ?
C14 C15 H15A 118.7 . . ?
C16 C15 H15A 118.7 . . ?
C11 C16 C15 117.1(3) . . ?
C11 C16 C17 123.3(3) . . ?
C15 C16 C17 119.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C26 122.7(3) . . ?
C22 C21 N2 118.0(2) . . ?
C26 C21 N2 119.3(2) . . ?
C23 C22 C21 116.9(3) . . ?
C23 C22 C28 120.7(3) . . ?
C21 C22 C28 122.4(3) . . ?
C24 C23 C22 122.1(3) . . ?
C24 C23 H23A 118.9 . . ?
C22 C23 H23A 118.9 . . ?
C25 C24 C23 118.1(3) . . ?
C25 C24 C29 120.2(3) . . ?
C23 C24 C29 121.6(3) . . ?
C24 C25 C26 122.6(3) . . ?
C24 C25 H25A 118.7 . . ?
C26 C25 H25A 118.7 . . ?
C25 C26 C21 116.8(3) . . ?
C25 C26 C27 119.9(3) . . ?
C21 C26 C27 123.3(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 C32 111.5(2) . . ?
N3 C30 C31 111.8(3) . . ?
C32 C30 C31 110.1(3) . . ?
N3 C30 H30A 107.8 . . ?
C32 C30 H30A 107.8 . . ?
C31 C30 H30A 107.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N3 C33 C35 112.4(3) . . ?
N3 C33 C34 112.3(3) . . ?
C35 C33 C34 113.9(3) . . ?
N3 C33 H33A 105.8 . . ?
C35 C33 H33A 105.8 . . ?
C34 C33 H33A 105.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
Cl2 C40 Cl3 112.8(2) . . ?
Cl2 C40 H40A 109.0 . . ?
Cl3 C40 H40A 109.0 . . ?
Cl2 C40 H40B 109.0 . . ?
Cl3 C40 H40B 109.0 . . ?
H40A C40 H40B 107.8 . . ?
F1 C41 F2 106.8(3) . . ?
F1 C41 F3 107.7(3) . . ?
F2 C41 F3 106.7(3) . . ?
F1 C41 S1 111.1(2) . . ?
F2 C41 S1 112.5(2) . . ?
F3 C41 S1 111.7(2) . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-radical
_database_code_depnum_ccdc_archive 'CCDC 1448867'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            DAC-BCl-N(iPr)2-radical
_chemical_melting_point          ?
_chemical_formula_moiety         {(C24H28N2O2)-B-Cl-N(C3H7)2-C6H6
_chemical_formula_sum            'C33 H45 B Cl N3 O2'
_chemical_formula_weight         561.98

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'
Cl Cl 0.1484 0.1585 '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'
B B 0.0013 0.0007 '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                   8.2331(18)
_cell_length_b                   11.975(3)
_cell_length_c                   16.574(4)
_cell_angle_alpha                75.271(5)
_cell_angle_beta                 87.907(5)
_cell_angle_gamma                84.925(4)
_cell_volume                     1573.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6091
_cell_measurement_theta_min      1.2660
_cell_measurement_theta_max      27.4773

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21212
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             5540
_reflns_number_gt                4540
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0737P)²+2.1522P] 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         5540
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.02478(8) 0.77667(6) 0.20283(6) 0.0462(3) Uani 1 1 d . . . . .
O1 O -0.1844(2) 0.38569(15) 0.40944(11) 0.0239(4) Uani 1 1 d . . . . .
N1 N -0.2190(2) 0.55870(17) 0.31292(12) 0.0176(4) Uani 1 1 d . . . . .
C1 C -0.2251(3) 0.6223(2) 0.22928(15) 0.0179(5) Uani 1 1 d . . . . .
B1 B -0.1906(3) 0.7542(2) 0.20323(17) 0.0196(6) Uani 1 1 d . . . . .
O2 O -0.1885(2) 0.38021(15) 0.14040(11) 0.0257(4) Uani 1 1 d . . . . .
N2 N -0.2193(2) 0.55616(17) 0.17019(12) 0.0174(4) Uani 1 1 d . . . . .
C2 C -0.1667(3) 0.4426(2) 0.33798(15) 0.0187(5) Uani 1 1 d . . . . .
N3 N -0.3025(2) 0.84888(17) 0.18235(12) 0.0183(4) Uani 1 1 d . . . . .
C3 C -0.0787(3) 0.3933(2) 0.27058(15) 0.0187(5) Uani 1 1 d . . . . .
C4 C -0.1679(3) 0.4395(2) 0.18821(15) 0.0188(5) Uani 1 1 d . . . . .
C5 C -0.0705(3) 0.2614(2) 0.29646(16) 0.0241(6) Uani 1 1 d . . . . .
H5A H -0.0138 0.2303 0.2529 0.036 Uiso 1 1 calc R U . . .
H5B H -0.0111 0.2329 0.3489 0.036 Uiso 1 1 calc R U . . .
H5C H -0.1813 0.2361 0.3043 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0950(3) 0.4353(2) 0.25915(16) 0.0220(5) Uani 1 1 d . . . . .
H6A H 0.1540 0.4045 0.2160 0.033 Uiso 1 1 calc R U . . .
H6B H 0.0878 0.5201 0.2423 0.033 Uiso 1 1 calc R U . . .
H6C H 0.1534 0.4077 0.3119 0.033 Uiso 1 1 calc R U . . .
C11 C -0.2774(3) 0.6140(2) 0.37798(15) 0.0184(5) Uani 1 1 d . . . . .
C12 C -0.4447(3) 0.6199(2) 0.39754(15) 0.0199(5) Uani 1 1 d . . . . .
C13 C -0.4980(3) 0.6720(2) 0.46065(15) 0.0231(6) Uani 1 1 d . . . . .
H13A H -0.6112 0.6779 0.4738 0.028 Uiso 1 1 calc R U . . .
C14 C -0.3908(3) 0.7156(2) 0.50513(16) 0.0241(6) Uani 1 1 d . . . . .
C15 C -0.2246(3) 0.7035(2) 0.48674(16) 0.0254(6) Uani 1 1 d . . . . .
H15A H -0.1498 0.7314 0.5178 0.030 Uiso 1 1 calc R U . . .
C16 C -0.1649(3) 0.6517(2) 0.42417(16) 0.0219(5) Uani 1 1 d . . . . .
C17 C 0.0168(3) 0.6312(3) 0.41222(19) 0.0316(6) Uani 1 1 d . . . . .
H17A H 0.0385 0.5944 0.3660 0.047 Uiso 1 1 calc R U . . .
H17B H 0.0660 0.7054 0.3994 0.047 Uiso 1 1 calc R U . . .
H17C H 0.0638 0.5805 0.4635 0.047 Uiso 1 1 calc R U . . .
C18 C -0.5663(3) 0.5675(2) 0.35501(16) 0.0250(6) Uani 1 1 d . . . . .
H18A H -0.5101 0.5344 0.3122 0.037 Uiso 1 1 calc R U . . .
H18B H -0.6173 0.5063 0.3963 0.037 Uiso 1 1 calc R U . . .
H18C H -0.6503 0.6276 0.3289 0.037 Uiso 1 1 calc R U . . .
C19 C -0.4516(4) 0.7715(3) 0.57349(18) 0.0339(7) Uani 1 1 d . . . . .
H19A H -0.3592 0.7970 0.5978 0.051 Uiso 1 1 calc R U . . .
H19B H -0.5283 0.8385 0.5503 0.051 Uiso 1 1 calc R U . . .
H19C H -0.5070 0.7154 0.6168 0.051 Uiso 1 1 calc R U . . .
C21 C -0.2729(3) 0.6106(2) 0.08564(15) 0.0195(5) Uani 1 1 d . . . . .
C22 C -0.1564(3) 0.6518(2) 0.02402(16) 0.0235(6) Uani 1 1 d . . . . .
C23 C -0.2103(3) 0.7027(2) -0.05663(16) 0.0260(6) Uani 1 1 d . . . . .
H23A H -0.1335 0.7342 -0.0986 0.031 Uiso 1 1 calc R U . . .
C24 C -0.3741(3) 0.7087(2) -0.07775(16) 0.0235(6) Uani 1 1 d . . . . .
C25 C -0.4847(3) 0.6619(2) -0.01580(16) 0.0239(6) Uani 1 1 d . . . . .
H25A H -0.5959 0.6633 -0.0298 0.029 Uiso 1 1 calc R U . . .
C26 C -0.4372(3) 0.6130(2) 0.06616(15) 0.0206(5) Uani 1 1 d . . . . .
C27 C -0.5627(3) 0.5608(2) 0.13034(16) 0.0254(6) Uani 1 1 d . . . . .
H27A H -0.5107 0.5301 0.1846 0.038 Uiso 1 1 calc R U . . .
H27B H -0.6496 0.6205 0.1346 0.038 Uiso 1 1 calc R U . . .
H27C H -0.6092 0.4978 0.1134 0.038 Uiso 1 1 calc R U . . .
C28 C 0.0241(3) 0.6369(3) 0.04114(18) 0.0363(7) Uani 1 1 d . . . . .
H28A H 0.0418 0.6001 0.1004 0.054 Uiso 1 1 calc R U . . .
H28B H 0.0791 0.5880 0.0074 0.054 Uiso 1 1 calc R U . . .
H28C H 0.0685 0.7129 0.0267 0.054 Uiso 1 1 calc R U . . .
C29 C -0.4283(4) 0.7607(2) -0.16631(17) 0.0299(6) Uani 1 1 d . . . . .
H29A H -0.3344 0.7893 -0.2011 0.045 Uiso 1 1 calc R U . . .
H29B H -0.4746 0.7016 -0.1878 0.045 Uiso 1 1 calc R U . . .
H29C H -0.5110 0.8252 -0.1676 0.045 Uiso 1 1 calc R U . . .
C30 C -0.4797(3) 0.8325(2) 0.18848(17) 0.0242(6) Uani 1 1 d . . . . .
H30A H -0.4905 0.7472 0.2054 0.029 Uiso 1 1 calc R U . . .
C31 C -0.5639(3) 0.8797(2) 0.10488(19) 0.0331(7) Uani 1 1 d . . . . .
H31A H -0.6802 0.8672 0.1117 0.050 Uiso 1 1 calc R U . . .
H31B H -0.5511 0.9628 0.0848 0.050 Uiso 1 1 calc R U . . .
H31C H -0.5147 0.8394 0.0643 0.050 Uiso 1 1 calc R U . . .
C32 C -0.5631(3) 0.8833(2) 0.2563(2) 0.0352(7) Uani 1 1 d . . . . .
H32A H -0.6795 0.8712 0.2588 0.053 Uiso 1 1 calc R U . . .
H32B H -0.5138 0.8449 0.3103 0.053 Uiso 1 1 calc R U . . .
H32C H -0.5496 0.9665 0.2435 0.053 Uiso 1 1 calc R U . . .
C33 C -0.2645(3) 0.9726(2) 0.15253(17) 0.0268(6) Uani 1 1 d . . . . .
H33A H -0.3719 1.0186 0.1395 0.032 Uiso 1 1 calc R U . . .
C34 C -0.1897(4) 1.0177(3) 0.2191(2) 0.0429(8) Uani 1 1 d . . . . .
H34A H -0.1676 1.0988 0.1960 0.064 Uiso 1 1 calc R U . . .
H34B H -0.2658 1.0121 0.2666 0.064 Uiso 1 1 calc R U . . .
H34C H -0.0876 0.9713 0.2377 0.064 Uiso 1 1 calc R U . . .
C35 C -0.1667(4) 0.9965(3) 0.07141(19) 0.0395(7) Uani 1 1 d . . . . .
H35A H -0.1453 1.0785 0.0548 0.059 Uiso 1 1 calc R U . . .
H35B H -0.0630 0.9484 0.0793 0.059 Uiso 1 1 calc R U . . .
H35C H -0.2288 0.9780 0.0278 0.059 Uiso 1 1 calc R U . . .
C40 C 0.1443(5) 0.9542(3) 0.4727(2) 0.0568(10) Uani 1 1 d . . . . .
H40A H 0.2437 0.9225 0.4535 0.068 Uiso 1 1 calc R U . . .
C41 C -0.0003(5) 0.9504(3) 0.4337(2) 0.0571(10) Uani 1 1 d . . . . .
H41A H -0.0001 0.9160 0.3879 0.068 Uiso 1 1 calc R U . . .
C42 C -0.1449(5) 0.9967(3) 0.4614(3) 0.0577(10) Uani 1 1 d . . . . .
H42A H -0.2443 0.9945 0.4348 0.069 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 1.817(3) . ?
O1 C2 1.218(3) . ?
N1 C2 1.380(3) . ?
N1 C1 1.402(3) . ?
N1 C11 1.450(3) . ?
C1 N2 1.405(3) . ?
C1 B1 1.576(4) . ?
B1 N3 1.376(4) . ?
O2 C4 1.215(3) . ?
N2 C4 1.383(3) . ?
N2 C21 1.454(3) . ?
C2 C3 1.524(3) . ?
N3 C30 1.486(3) . ?
N3 C33 1.495(3) . ?
C3 C4 1.525(3) . ?
C3 C5 1.524(3) . ?
C3 C6 1.547(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 C16 1.397(4) . ?
C11 C12 1.403(3) . ?
C12 C13 1.387(4) . ?
C12 C18 1.510(4) . ?
C13 C14 1.386(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.394(4) . ?
C14 C19 1.506(4) . ?
C15 C16 1.392(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.508(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C26 1.398(3) . ?
C21 C22 1.401(4) . ?
C22 C23 1.392(4) . ?
C22 C28 1.509(4) . ?
C23 C24 1.396(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.388(4) . ?
C24 C29 1.508(4) . ?
C25 C26 1.391(4) . ?
C25 H25A 0.9500 . ?
C26 C27 1.512(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.524(4) . ?
C30 C32 1.524(4) . ?
C30 H30A 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.516(4) . ?
C33 C35 1.518(4) . ?
C33 H33A 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C40 C42 1.366(6) 2_576 ?
C40 C41 1.385(5) . ?
C40 H40A 0.9500 . ?
C41 C42 1.382(6) . ?
C41 H41A 0.9500 . ?
C42 C40 1.366(6) 2_576 ?
C42 H42A 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
C2 N1 C1 123.7(2) . . ?
C2 N1 C11 116.65(19) . . ?
C1 N1 C11 119.57(19) . . ?
N1 C1 N2 115.5(2) . . ?
N1 C1 B1 121.2(2) . . ?
N2 C1 B1 121.1(2) . . ?
N3 B1 C1 127.7(2) . . ?
N3 B1 Cl1 119.2(2) . . ?
C1 B1 Cl1 113.15(18) . . ?
C4 N2 C1 123.5(2) . . ?
C4 N2 C21 117.11(19) . . ?
C1 N2 C21 119.38(19) . . ?
O1 C2 N1 122.1(2) . . ?
O1 C2 C3 123.0(2) . . ?
N1 C2 C3 114.8(2) . . ?
B1 N3 C30 119.9(2) . . ?
B1 N3 C33 126.1(2) . . ?
C30 N3 C33 113.99(19) . . ?
C2 C3 C4 109.67(19) . . ?
C2 C3 C5 109.9(2) . . ?
C4 C3 C5 110.4(2) . . ?
C2 C3 C6 108.05(19) . . ?
C4 C3 C6 108.37(19) . . ?
C5 C3 C6 110.4(2) . . ?
O2 C4 N2 122.0(2) . . ?
O2 C4 C3 123.2(2) . . ?
N2 C4 C3 114.7(2) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C16 C11 C12 121.4(2) . . ?
C16 C11 N1 119.2(2) . . ?
C12 C11 N1 119.1(2) . . ?
C13 C12 C11 118.2(2) . . ?
C13 C12 C18 119.3(2) . . ?
C11 C12 C18 122.4(2) . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C13 C14 C15 118.4(2) . . ?
C13 C14 C19 120.9(2) . . ?
C15 C14 C19 120.7(2) . . ?
C16 C15 C14 121.9(2) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C15 C16 C11 117.9(2) . . ?
C15 C16 C17 119.6(2) . . ?
C11 C16 C17 122.4(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C21 C22 121.4(2) . . ?
C26 C21 N2 119.5(2) . . ?
C22 C21 N2 119.0(2) . . ?
C23 C22 C21 118.0(2) . . ?
C23 C22 C28 119.5(2) . . ?
C21 C22 C28 122.4(2) . . ?
C22 C23 C24 121.9(2) . . ?
C22 C23 H23A 119.0 . . ?
C24 C23 H23A 119.0 . . ?
C25 C24 C23 118.3(2) . . ?
C25 C24 C29 120.9(2) . . ?
C23 C24 C29 120.8(2) . . ?
C24 C25 C26 121.8(2) . . ?
C24 C25 H25A 119.1 . . ?
C26 C25 H25A 119.1 . . ?
C25 C26 C21 118.5(2) . . ?
C25 C26 C27 119.3(2) . . ?
C21 C26 C27 122.2(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 C31 112.2(2) . . ?
N3 C30 C32 111.4(2) . . ?
C31 C30 C32 111.6(2) . . ?
N3 C30 H30A 107.1 . . ?
C31 C30 H30A 107.1 . . ?
C32 C30 H30A 107.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N3 C33 C34 113.2(2) . . ?
N3 C33 C35 112.9(2) . . ?
C34 C33 C35 112.5(2) . . ?
N3 C33 H33A 105.8 . . ?
C34 C33 H33A 105.8 . . ?
C35 C33 H33A 105.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C42 C40 C41 120.4(4) 2_576 . ?
C42 C40 H40A 119.8 2_576 . ?
C41 C40 H40A 119.8 . . ?
C42 C41 C40 119.8(4) . . ?
C42 C41 H41A 120.1 . . ?
C40 C41 H41A 120.1 . . ?
C40 C42 C41 119.8(4) 2_576 . ?
C40 C42 H42A 120.1 2_576 . ?
C41 C42 H42A 120.1 . . ?

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
C2 N1 C1 N2 17.4(3) . . . . ?
C11 N1 C1 N2 -159.50(19) . . . . ?
C2 N1 C1 B1 -146.1(2) . . . . ?
C11 N1 C1 B1 37.0(3) . . . . ?
N1 C1 B1 N3 -102.9(3) . . . . ?
N2 C1 B1 N3 94.5(3) . . . . ?
N1 C1 B1 Cl1 76.7(3) . . . . ?
N2 C1 B1 Cl1 -85.9(2) . . . . ?
N1 C1 N2 C4 -16.9(3) . . . . ?
B1 C1 N2 C4 146.6(2) . . . . ?
N1 C1 N2 C21 161.71(19) . . . . ?
B1 C1 N2 C21 -34.8(3) . . . . ?
C1 N1 C2 O1 -169.2(2) . . . . ?
C11 N1 C2 O1 7.7(3) . . . . ?
C1 N1 C2 C3 13.5(3) . . . . ?
C11 N1 C2 C3 -169.59(19) . . . . ?
C1 B1 N3 C30 4.2(4) . . . . ?
Cl1 B1 N3 C30 -175.42(18) . . . . ?
C1 B1 N3 C33 -175.7(2) . . . . ?
Cl1 B1 N3 C33 4.7(3) . . . . ?
O1 C2 C3 C4 140.4(2) . . . . ?
N1 C2 C3 C4 -42.3(3) . . . . ?
O1 C2 C3 C5 18.9(3) . . . . ?
N1 C2 C3 C5 -163.8(2) . . . . ?
O1 C2 C3 C6 -101.7(3) . . . . ?
N1 C2 C3 C6 75.6(2) . . . . ?
C1 N2 C4 O2 167.9(2) . . . . ?
C21 N2 C4 O2 -10.7(3) . . . . ?
C1 N2 C4 C3 -14.3(3) . . . . ?
C21 N2 C4 C3 167.11(19) . . . . ?
C2 C3 C4 O2 -139.5(2) . . . . ?
C5 C3 C4 O2 -18.3(3) . . . . ?
C6 C3 C4 O2 102.7(3) . . . . ?
C2 C3 C4 N2 42.7(3) . . . . ?
C5 C3 C4 N2 163.9(2) . . . . ?
C6 C3 C4 N2 -75.1(2) . . . . ?
C2 N1 C11 C16 81.6(3) . . . . ?
C1 N1 C11 C16 -101.3(3) . . . . ?
C2 N1 C11 C12 -93.2(3) . . . . ?
C1 N1 C11 C12 83.8(3) . . . . ?
C16 C11 C12 C13 4.5(4) . . . . ?
N1 C11 C12 C13 179.2(2) . . . . ?
C16 C11 C12 C18 -172.9(2) . . . . ?
N1 C11 C12 C18 1.9(3) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C18 C12 C13 C14 176.2(2) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C12 C13 C14 C19 -179.9(2) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C19 C14 C15 C16 179.7(2) . . . . ?
C14 C15 C16 C11 1.6(4) . . . . ?
C14 C15 C16 C17 -174.5(2) . . . . ?
C12 C11 C16 C15 -4.6(4) . . . . ?
N1 C11 C16 C15 -179.4(2) . . . . ?
C12 C11 C16 C17 171.3(2) . . . . ?
N1 C11 C16 C17 -3.4(4) . . . . ?
C4 N2 C21 C26 90.4(3) . . . . ?
C1 N2 C21 C26 -88.3(3) . . . . ?
C4 N2 C21 C22 -84.9(3) . . . . ?
C1 N2 C21 C22 96.4(3) . . . . ?
C26 C21 C22 C23 4.2(4) . . . . ?
N2 C21 C22 C23 179.4(2) . . . . ?
C26 C21 C22 C28 -172.2(3) . . . . ?
N2 C21 C22 C28 2.9(4) . . . . ?
C21 C22 C23 C24 -2.8(4) . . . . ?
C28 C22 C23 C24 173.8(3) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C22 C23 C24 C29 -178.0(2) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C29 C24 C25 C26 179.7(2) . . . . ?
C24 C25 C26 C21 -0.6(4) . . . . ?
C24 C25 C26 C27 -178.5(2) . . . . ?
C22 C21 C26 C25 -2.6(4) . . . . ?
N2 C21 C26 C25 -177.8(2) . . . . ?
C22 C21 C26 C27 175.3(2) . . . . ?
N2 C21 C26 C27 0.1(3) . . . . ?
B1 N3 C30 C31 -120.5(2) . . . . ?
C33 N3 C30 C31 59.4(3) . . . . ?
B1 N3 C30 C32 113.5(3) . . . . ?
C33 N3 C30 C32 -66.7(3) . . . . ?
B1 N3 C33 C34 -68.1(3) . . . . ?
C30 N3 C33 C34 112.0(3) . . . . ?
B1 N3 C33 C35 61.1(3) . . . . ?
C30 N3 C33 C35 -118.7(2) . . . . ?
C42 C40 C41 C42 0.1(6) 2_576 . . . ?
C40 C41 C42 C40 -0.1(6) . . . 2_576 ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.059

