# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_les099_compound_9b
_database_code_depnum_ccdc_archive 'CCDC 912582'
_audit_update_record             
;
2012-11-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
#TrackingRef 'kosta_Angew_2012.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
chloro(perfluorophenyl)(3-(2,2,6,6-tetramethylpiperidin-1-ium-1-yl)-
phenyl)hydroborate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 B Cl F5 N'
_chemical_formula_sum            'C21 H24 B Cl F5 N'
_chemical_formula_weight         431.67
_chemical_absolute_configuration ad

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_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                   10.8901(7)
_cell_length_b                   12.3059(7)
_cell_length_c                   15.2966(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2049.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    509
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8524
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
dx = 35 mm, 60 sec./deg., 2 deg., 11 sets, 414 frames,
18501 refl. postref.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47114
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4689
_reflns_number_gt                4364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Determination of absolute structure using Bayesian statistics on Bijvoet
differences (Hooft, Straver and Spek, 2008): y = -0.008(12)
(Platon: Spek, 2003)

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.5190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_number_reflns         4689
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.26528(4) 0.52746(3) 0.50335(3) 0.02578(10) Uani 1 1 d . . .
B1 B 0.44260(16) 0.50580(14) 0.50326(13) 0.0210(3) Uani 1 1 d . . .
H1 H 0.4798(18) 0.5588(17) 0.5618(13) 0.025 Uiso 1 1 d . . .
C1 C 0.51623(14) 0.54378(13) 0.41586(10) 0.0184(3) Uani 1 1 d . . .
C2 C 0.63710(15) 0.50154(13) 0.40987(11) 0.0240(3) Uani 1 1 d . . .
H2 H 0.6615 0.4472 0.4504 0.029 Uiso 1 1 calc R . .
C3 C 0.72113(16) 0.53546(15) 0.34806(12) 0.0278(4) Uani 1 1 d . . .
H3 H 0.8014 0.5053 0.3474 0.033 Uiso 1 1 calc R . .
C4 C 0.68850(17) 0.61312(15) 0.28729(13) 0.0299(4) Uani 1 1 d . . .
H4 H 0.7459 0.6365 0.2445 0.036 Uiso 1 1 calc R . .
C5 C 0.57162(16) 0.65643(13) 0.28930(11) 0.0241(3) Uani 1 1 d . . .
H5 H 0.5482 0.7097 0.2476 0.029 Uiso 1 1 calc R . .
C6 C 0.48802(14) 0.62218(12) 0.35243(10) 0.0181(3) Uani 1 1 d . . .
N7 N 0.36426(12) 0.67323(10) 0.35406(8) 0.0162(3) Uani 1 1 d . . .
H7 H 0.3271(18) 0.6391(16) 0.3937(13) 0.019 Uiso 1 1 d . . .
C8 C 0.36416(15) 0.79360(12) 0.38856(11) 0.0211(3) Uani 1 1 d . . .
C9 C 0.22903(17) 0.82671(14) 0.40025(11) 0.0274(4) Uani 1 1 d . . .
H9A H 0.1946 0.7864 0.4506 0.033 Uiso 1 1 calc R . .
H9B H 0.2256 0.9051 0.4146 0.033 Uiso 1 1 calc R . .
C10 C 0.14853(18) 0.80576(15) 0.32054(13) 0.0302(4) Uani 1 1 d . . .
H10A H 0.1793 0.8481 0.2701 0.036 Uiso 1 1 calc R . .
H10B H 0.0632 0.8289 0.3328 0.036 Uiso 1 1 calc R . .
C11 C 0.15143(16) 0.68467(15) 0.29922(12) 0.0265(4) Uani 1 1 d . . .
H11A H 0.0944 0.6702 0.2502 0.032 Uiso 1 1 calc R . .
H11B H 0.1218 0.6434 0.3506 0.032 Uiso 1 1 calc R . .
C12 C 0.27946(15) 0.64366(12) 0.27443(10) 0.0197(3) Uani 1 1 d . . .
C13 C 0.27791(17) 0.51997(13) 0.26743(11) 0.0257(3) Uani 1 1 d . . .
H13A H 0.2515 0.4887 0.3233 0.039 Uiso 1 1 calc R . .
H13B H 0.3605 0.4938 0.2532 0.039 Uiso 1 1 calc R . .
H13C H 0.2207 0.4979 0.2213 0.039 Uiso 1 1 calc R . .
C14 C 0.32077(19) 0.69050(15) 0.18640(11) 0.0292(4) Uani 1 1 d . . .
H14A H 0.4030 0.6634 0.1723 0.044 Uiso 1 1 calc R . .
H14B H 0.3226 0.7700 0.1899 0.044 Uiso 1 1 calc R . .
H14C H 0.2631 0.6681 0.1407 0.044 Uiso 1 1 calc R . .
C15 C 0.43398(19) 0.87281(14) 0.33042(13) 0.0305(4) Uani 1 1 d . . .
H15A H 0.3959 0.8748 0.2724 0.046 Uiso 1 1 calc R . .
H15B H 0.5195 0.8491 0.3250 0.046 Uiso 1 1 calc R . .
H15C H 0.4315 0.9455 0.3564 0.046 Uiso 1 1 calc R . .
C16 C 0.42554(17) 0.79153(14) 0.47839(11) 0.0281(4) Uani 1 1 d . . .
H16A H 0.3817 0.7407 0.5166 0.042 Uiso 1 1 calc R . .
H16B H 0.4232 0.8645 0.5040 0.042 Uiso 1 1 calc R . .
H16C H 0.5111 0.7681 0.4722 0.042 Uiso 1 1 calc R . .
C17 C 0.46255(16) 0.37673(13) 0.52334(10) 0.0223(3) Uani 1 1 d . . .
C18 C 0.52818(15) 0.34156(13) 0.59524(11) 0.0219(3) Uani 1 1 d . . .
F18 F 0.58128(10) 0.41439(8) 0.65002(7) 0.0310(2) Uani 1 1 d . . .
C19 C 0.54390(15) 0.23335(14) 0.61772(12) 0.0244(3) Uani 1 1 d . . .
F19 F 0.60677(10) 0.20520(9) 0.68980(8) 0.0354(3) Uani 1 1 d . . .
C20 C 0.49226(16) 0.15412(14) 0.56600(13) 0.0272(4) Uani 1 1 d . . .
F20 F 0.50410(11) 0.04883(8) 0.58655(8) 0.0381(3) Uani 1 1 d . . .
C21 C 0.42663(17) 0.18495(14) 0.49262(13) 0.0297(4) Uani 1 1 d . . .
F21 F 0.37446(13) 0.10840(9) 0.44151(9) 0.0454(3) Uani 1 1 d . . .
C22 C 0.41434(17) 0.29368(15) 0.47268(11) 0.0275(4) Uani 1 1 d . . .
F22 F 0.35234(13) 0.31800(9) 0.39880(7) 0.0403(3) 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
Cl1 B1 1.9494(18) . ?
B1 C1 1.627(2) . ?
B1 C17 1.632(2) . ?
B1 H1 1.18(2) . ?
C1 C6 1.402(2) . ?
C1 C2 1.418(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 N7 1.487(2) . ?
N7 C12 1.571(2) . ?
N7 C8 1.5724(19) . ?
N7 H7 0.84(2) . ?
C8 C15 1.523(2) . ?
C8 C16 1.528(2) . ?
C8 C9 1.537(2) . ?
C9 C10 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.531(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.526(2) . ?
C12 C14 1.532(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.381(2) . ?
C17 C22 1.386(2) . ?
C18 F18 1.3565(19) . ?
C18 C19 1.386(2) . ?
C19 F19 1.343(2) . ?
C19 C20 1.376(3) . ?
C20 F20 1.3395(19) . ?
C20 C21 1.384(3) . ?
C21 F21 1.350(2) . ?
C21 C22 1.379(3) . ?
C22 F22 1.350(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 C17 111.62(13) . . ?
C1 B1 Cl1 116.71(11) . . ?
C17 B1 Cl1 105.35(11) . . ?
C1 B1 H1 107.2(10) . . ?
C17 B1 H1 110.4(10) . . ?
Cl1 B1 H1 105.3(10) . . ?
C6 C1 C2 114.25(14) . . ?
C6 C1 B1 131.15(14) . . ?
C2 C1 B1 113.90(14) . . ?
C3 C2 C1 123.28(16) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C4 C3 C2 120.01(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.34(16) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.10(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 123.01(15) . . ?
C5 C6 N7 118.44(14) . . ?
C1 C6 N7 118.53(14) . . ?
C6 N7 C12 114.95(12) . . ?
C6 N7 C8 113.84(12) . . ?
C12 N7 C8 118.55(12) . . ?
C6 N7 H7 103.7(13) . . ?
C12 N7 H7 99.2(13) . . ?
C8 N7 H7 103.2(13) . . ?
C15 C8 C16 108.50(14) . . ?
C15 C8 C9 112.10(14) . . ?
C16 C8 C9 108.57(14) . . ?
C15 C8 N7 113.99(13) . . ?
C16 C8 N7 106.60(12) . . ?
C9 C8 N7 106.82(13) . . ?
C10 C9 C8 114.38(14) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 108.93(14) . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 C12 113.20(15) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 109.65(14) . . ?
C13 C12 C14 108.48(14) . . ?
C11 C12 C14 111.17(14) . . ?
C13 C12 N7 106.97(13) . . ?
C11 C12 N7 105.48(12) . . ?
C14 C12 N7 114.93(13) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 114.22(15) . . ?
C18 C17 B1 121.57(15) . . ?
C22 C17 B1 124.19(15) . . ?
F18 C18 C17 120.36(14) . . ?
F18 C18 C19 115.40(15) . . ?
C17 C18 C19 124.23(16) . . ?
F19 C19 C20 119.84(15) . . ?
F19 C19 C18 120.95(16) . . ?
C20 C19 C18 119.19(16) . . ?
F20 C20 C19 120.75(17) . . ?
F20 C20 C21 120.35(17) . . ?
C19 C20 C21 118.90(15) . . ?
F21 C21 C22 120.55(18) . . ?
F21 C21 C20 119.74(16) . . ?
C22 C21 C20 119.71(16) . . ?
F22 C22 C21 116.67(16) . . ?
F22 C22 C17 119.61(16) . . ?
C21 C22 C17 123.72(17) . . ?

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
C17 B1 C1 C6 146.89(16) . . . . ?
Cl1 B1 C1 C6 25.7(2) . . . . ?
C17 B1 C1 C2 -43.43(18) . . . . ?
Cl1 B1 C1 C2 -164.64(12) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
B1 C1 C2 C3 -170.48(15) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 N7 178.19(14) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
B1 C1 C6 C5 169.18(16) . . . . ?
C2 C1 C6 N7 -178.82(13) . . . . ?
B1 C1 C6 N7 -9.2(2) . . . . ?
C5 C6 N7 C12 69.13(18) . . . . ?
C1 C6 N7 C12 -112.46(15) . . . . ?
C5 C6 N7 C8 -72.31(18) . . . . ?
C1 C6 N7 C8 106.11(16) . . . . ?
C6 N7 C8 C15 64.77(18) . . . . ?
C12 N7 C8 C15 -75.17(18) . . . . ?
C6 N7 C8 C16 -54.91(17) . . . . ?
C12 N7 C8 C16 165.14(13) . . . . ?
C6 N7 C8 C9 -170.84(13) . . . . ?
C12 N7 C8 C9 49.21(18) . . . . ?
C15 C8 C9 C10 74.39(19) . . . . ?
C16 C8 C9 C10 -165.76(15) . . . . ?
N7 C8 C9 C10 -51.14(19) . . . . ?
C8 C9 C10 C11 59.5(2) . . . . ?
C9 C10 C11 C12 -62.8(2) . . . . ?
C10 C11 C12 C13 171.67(14) . . . . ?
C10 C11 C12 C14 -68.38(19) . . . . ?
C10 C11 C12 N7 56.81(18) . . . . ?
C6 N7 C12 C13 51.85(17) . . . . ?
C8 N7 C12 C13 -168.63(13) . . . . ?
C6 N7 C12 C11 168.55(13) . . . . ?
C8 N7 C12 C11 -51.92(17) . . . . ?
C6 N7 C12 C14 -68.63(17) . . . . ?
C8 N7 C12 C14 70.89(18) . . . . ?
C1 B1 C17 C18 111.97(17) . . . . ?
Cl1 B1 C17 C18 -120.43(15) . . . . ?
C1 B1 C17 C22 -69.6(2) . . . . ?
Cl1 B1 C17 C22 57.99(19) . . . . ?
C22 C17 C18 F18 179.43(15) . . . . ?
B1 C17 C18 F18 -2.0(2) . . . . ?
C22 C17 C18 C19 -1.4(3) . . . . ?
B1 C17 C18 C19 177.20(16) . . . . ?
F18 C18 C19 F19 0.7(2) . . . . ?
C17 C18 C19 F19 -178.53(15) . . . . ?
F18 C18 C19 C20 179.55(15) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
F19 C19 C20 F20 -0.1(2) . . . . ?
C18 C19 C20 F20 -178.99(15) . . . . ?
F19 C19 C20 C21 179.23(15) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
F20 C20 C21 F21 -0.1(2) . . . . ?
C19 C20 C21 F21 -179.45(16) . . . . ?
F20 C20 C21 C22 179.46(16) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
F21 C21 C22 F22 -2.4(3) . . . . ?
C20 C21 C22 F22 178.07(16) . . . . ?
F21 C21 C22 C17 178.24(17) . . . . ?
C20 C21 C22 C17 -1.3(3) . . . . ?
C18 C17 C22 F22 -177.49(15) . . . . ?
B1 C17 C22 F22 4.0(3) . . . . ?
C18 C17 C22 C21 1.9(3) . . . . ?
B1 C17 C22 C21 -176.66(16) . . . . ?

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
N7 H7 Cl1 0.84(2) 2.27(2) 3.0976(14) 167.7(18) .
C13 H13A Cl1 0.98 2.80 3.6126(18) 140.8 .
C3 H3 F20 0.95 2.52 3.402(2) 154.9 4_556
C4 H4 F18 0.95 2.45 3.288(2) 146.4 2_664
C15 H15C F21 0.98 2.47 3.422(2) 164.3 1_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_les095_c_compound_9c
_database_code_depnum_ccdc_archive 'CCDC 912583'
_audit_update_record             
;
2012-11-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
#TrackingRef 'kosta_Angew_2012.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dichloro(2-(2,2,6,6-tetramethylpiperidin-1-ium-1-yl)phenyl)hydroborate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 B Cl2 N'
_chemical_formula_sum            'C15 H24 B Cl2 N'
_chemical_formula_weight         300.06

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C m c 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   11.1847(5)
_cell_length_b                   11.3284(5)
_cell_length_c                   12.5977(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1596.19(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    97
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
dx = 35 mm, 60 sec./deg., 2 deg., 8 sets, 377 frames,
6782 refl. postref.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg,'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16342
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1921
_reflns_number_gt                1851
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Determination of absolute structure using Bayesian statistics on Bijvoet
differences (Hooft, Straver and Spek, 2008): y = 0.006(16)
(Platon: Spek, 2003).

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.6431P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_number_reflns         1921
_refine_ls_number_parameters     104
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.084
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.36309(2) 0.17603(2) 0.38679(4) 0.02378(9) Uani 1 1 d . . .
B1 B 0.5000 0.24141(17) 0.32246(15) 0.0155(4) Uani 1 2 d S . .
H1 H 0.5000 0.3395(18) 0.3473(17) 0.019 Uiso 1 2 d S . .
C2 C 0.5000 0.21369(15) 0.19715(13) 0.0149(3) Uani 1 2 d S . .
C3 C 0.5000 0.09575(16) 0.16246(14) 0.0197(4) Uani 1 2 d S . .
H3 H 0.5000 0.0347 0.2141 0.024 Uiso 1 2 calc SR . .
C4 C 0.5000 0.06499(18) 0.05639(16) 0.0262(4) Uani 1 2 d S . .
H4 H 0.5000 -0.0158 0.0361 0.031 Uiso 1 2 calc SR . .
C5 C 0.5000 0.15262(19) -0.02009(16) 0.0314(5) Uani 1 2 d S . .
H5 H 0.5000 0.1318 -0.0931 0.038 Uiso 1 2 calc SR . .
C6 C 0.5000 0.27117(18) 0.00938(14) 0.0263(4) Uani 1 2 d S . .
H6 H 0.5000 0.3316 -0.0429 0.032 Uiso 1 2 calc SR . .
C7 C 0.5000 0.29958(17) 0.11722(15) 0.0167(4) Uani 1 2 d S . .
N8 N 0.5000 0.42498(12) 0.15211(11) 0.0138(3) Uani 1 2 d S . .
H8 H 0.5000 0.4166(19) 0.2199(19) 0.017 Uiso 1 2 d S . .
C9 C 0.37926(9) 0.49260(14) 0.13480(15) 0.0197(2) Uani 1 1 d . . .
C10 C 0.38902(14) 0.60645(12) 0.19914(12) 0.0285(3) Uani 1 1 d . . .
H10A H 0.3173 0.6553 0.1853 0.034 Uiso 1 1 calc R . .
H10B H 0.3892 0.5862 0.2756 0.034 Uiso 1 1 calc R . .
C11 C 0.5000 0.67936(17) 0.17462(19) 0.0311(6) Uani 1 2 d S . .
H11A H 0.5000 0.7025 0.0988 0.037 Uiso 1 2 calc SR . .
H11B H 0.5000 0.7521 0.2182 0.037 Uiso 1 2 calc SR . .
C12 C 0.35041(12) 0.51722(13) 0.01852(11) 0.0260(3) Uani 1 1 d . . .
H12A H 0.3450 0.4424 -0.0202 0.039 Uiso 1 1 calc R . .
H12B H 0.4138 0.5660 -0.0125 0.039 Uiso 1 1 calc R . .
H12C H 0.2739 0.5591 0.0136 0.039 Uiso 1 1 calc R . .
C13 C 0.28117(12) 0.41399(13) 0.18175(13) 0.0307(3) Uani 1 1 d . . .
H13A H 0.2755 0.3408 0.1405 0.046 Uiso 1 1 calc R . .
H13B H 0.2045 0.4557 0.1791 0.046 Uiso 1 1 calc R . .
H13C H 0.3008 0.3951 0.2556 0.046 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.8842(11) . ?
B1 C2 1.610(2) . ?
B1 Cl1 1.8842(11) 4_655 ?
B1 H1 1.15(2) . ?
C2 C7 1.400(2) . ?
C2 C3 1.406(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 N8 1.487(2) . ?
N8 C9 1.5679(13) 4_655 ?
N8 C9 1.5679(13) . ?
N8 H8 0.86(2) . ?
C9 C12 1.526(2) . ?
C9 C10 1.527(2) . ?
C9 C13 1.5318(19) . ?
C10 C11 1.5226(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C10 1.5226(19) 4_655 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 B1 Cl1 110.19(8) . 4_655 ?
C2 B1 Cl1 110.19(8) . . ?
Cl1 B1 Cl1 108.72(9) 4_655 . ?
C2 B1 H1 117.0(10) . . ?
Cl1 B1 H1 105.2(6) 4_655 . ?
Cl1 B1 H1 105.2(6) . . ?
C7 C2 C3 115.90(16) . . ?
C7 C2 B1 124.73(15) . . ?
C3 C2 B1 119.36(15) . . ?
C4 C3 C2 122.73(17) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 119.53(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.40(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 118.78(18) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 122.66(18) . . ?
C6 C7 N8 120.52(16) . . ?
C2 C7 N8 116.82(15) . . ?
C7 N8 C9 115.19(8) . 4_655 ?
C7 N8 C9 115.19(8) . . ?
C9 N8 C9 118.94(14) 4_655 . ?
C7 N8 H8 100.8(14) . . ?
C9 N8 H8 101.1(7) 4_655 . ?
C9 N8 H8 101.1(7) . . ?
C12 C9 C10 111.74(13) . . ?
C12 C9 C13 109.00(12) . . ?
C10 C9 C13 109.71(13) . . ?
C12 C9 N8 113.89(13) . . ?
C10 C9 N8 106.09(11) . . ?
C13 C9 N8 106.21(12) . . ?
C11 C10 C9 114.13(13) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C10 109.21(15) 4_655 . ?
C10 C11 H11A 109.8 4_655 . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 4_655 . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 B1 C2 C7 -120.02(8) 4_655 . . . ?
Cl1 B1 C2 C7 120.02(8) . . . . ?
Cl1 B1 C2 C3 59.98(8) 4_655 . . . ?
Cl1 B1 C2 C3 -59.98(8) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
B1 C2 C3 C4 180.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C5 C6 C7 N8 180.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
B1 C2 C7 C6 180.0 . . . . ?
C3 C2 C7 N8 180.0 . . . . ?
B1 C2 C7 N8 0.0 . . . . ?
C6 C7 N8 C9 -72.15(11) . . . 4_655 ?
C2 C7 N8 C9 107.85(11) . . . 4_655 ?
C6 C7 N8 C9 72.15(11) . . . . ?
C2 C7 N8 C9 -107.85(11) . . . . ?
C7 N8 C9 C12 -70.10(16) . . . . ?
C9 N8 C9 C12 72.8(2) 4_655 . . . ?
C7 N8 C9 C10 166.57(13) . . . . ?
C9 N8 C9 C10 -50.5(2) 4_655 . . . ?
C7 N8 C9 C13 49.87(18) . . . . ?
C9 N8 C9 C13 -167.24(10) 4_655 . . . ?
C12 C9 C10 C11 -71.22(15) . . . . ?
C13 C9 C10 C11 167.78(13) . . . . ?
N8 C9 C10 C11 53.45(17) . . . . ?
C9 C10 C11 C10 -60.3(2) . . . 4_655 ?

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
N8 H8 H1 0.86(2) 1.83(3) 2.64(2) 158(2) .
B1 H1 H8 1.15(2) 1.83(3) 2.37(2) 102.8(15) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_les102_compound_10b
_database_code_depnum_ccdc_archive 'CCDC 912584'
_audit_update_record             
;
2012-11-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
#TrackingRef 'kosta_Angew_2012.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dichloro(perfluorophenyl(2-(2,2,6,6-tetramethylpiperidin-1-ium-1-yl)-
phenyl)borate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 B Cl2 F5 N'
_chemical_formula_sum            'C21 H23 B Cl2 F5 N'
_chemical_formula_weight         466.11

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_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'
'-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                   14.123(1)
_cell_length_b                   15.558(1)
_cell_length_c                   19.000(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4174.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    347
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8294
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
dx = 35 mm, 20 sec./deg., 1 deg., 1 set, 363 frames,
7916 refl. postref.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi, 1 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39511
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4789
_reflns_number_gt                3875
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0308P)²+3.1813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4789
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.21442(15) 0.55383(13) 0.60563(10) 0.0154(4) Uani 1 1 d . . .
Cl1 Cl 0.14418(3) 0.60133(3) 0.52778(2) 0.01692(10) Uani 1 1 d . . .
Cl2 Cl 0.12581(3) 0.50099(3) 0.66666(2) 0.01987(11) Uani 1 1 d . . .
C1 C 0.28810(12) 0.47618(11) 0.58627(9) 0.0142(4) Uani 1 1 d . . .
C2 C 0.34606(13) 0.45311(12) 0.64366(10) 0.0184(4) Uani 1 1 d . . .
H2 H 0.3421 0.4866 0.6854 0.022 Uiso 1 1 calc R . .
C3 C 0.40804(13) 0.38496(12) 0.64266(10) 0.0205(4) Uani 1 1 d . . .
H3 H 0.4455 0.3723 0.6829 0.025 Uiso 1 1 calc R . .
C4 C 0.41554(13) 0.33490(12) 0.58282(11) 0.0212(4) Uani 1 1 d . . .
H4 H 0.4580 0.2875 0.5816 0.025 Uiso 1 1 calc R . .
C5 C 0.36069(13) 0.35442(12) 0.52469(10) 0.0185(4) Uani 1 1 d . . .
H5 H 0.3655 0.3206 0.4832 0.022 Uiso 1 1 calc R . .
C6 C 0.29818(12) 0.42389(11) 0.52694(9) 0.0136(3) Uani 1 1 d . . .
N7 N 0.23853(10) 0.44045(9) 0.46363(7) 0.0129(3) Uani 1 1 d D . .
H7 H 0.2048(13) 0.4867(11) 0.4761(10) 0.015 Uiso 1 1 d D . .
C8 C 0.15791(12) 0.37263(11) 0.45078(10) 0.0157(4) Uani 1 1 d . . .
C9 C 0.09174(13) 0.41327(12) 0.39620(9) 0.0180(4) Uani 1 1 d . . .
H9A H 0.0426 0.3707 0.3832 0.022 Uiso 1 1 calc R . .
H9B H 0.0593 0.4630 0.4181 0.022 Uiso 1 1 calc R . .
C10 C 0.14127(13) 0.44347(13) 0.32959(9) 0.0204(4) Uani 1 1 d . . .
H10A H 0.0943 0.4690 0.2970 0.025 Uiso 1 1 calc R . .
H10B H 0.1710 0.3938 0.3057 0.025 Uiso 1 1 calc R . .
C11 C 0.21663(14) 0.50988(12) 0.34754(10) 0.0201(4) Uani 1 1 d . . .
H11A H 0.1856 0.5604 0.3692 0.024 Uiso 1 1 calc R . .
H11B H 0.2472 0.5293 0.3034 0.024 Uiso 1 1 calc R . .
C12 C 0.29319(13) 0.47654(12) 0.39779(9) 0.0167(4) Uani 1 1 d . . .
C13 C 0.35849(14) 0.41217(13) 0.36175(10) 0.0219(4) Uani 1 1 d . . .
H13A H 0.4061 0.3919 0.3954 0.033 Uiso 1 1 calc R . .
H13B H 0.3901 0.4400 0.3219 0.033 Uiso 1 1 calc R . .
H13C H 0.3212 0.3632 0.3448 0.033 Uiso 1 1 calc R . .
C14 C 0.35331(14) 0.55127(12) 0.42463(10) 0.0222(4) Uani 1 1 d . . .
H14A H 0.3125 0.5934 0.4480 0.033 Uiso 1 1 calc R . .
H14B H 0.3857 0.5786 0.3849 0.033 Uiso 1 1 calc R . .
H14C H 0.4003 0.5297 0.4582 0.033 Uiso 1 1 calc R . .
C15 C 0.10518(13) 0.36303(13) 0.52038(10) 0.0205(4) Uani 1 1 d . . .
H15A H 0.0822 0.4194 0.5358 0.031 Uiso 1 1 calc R . .
H15B H 0.1481 0.3395 0.5560 0.031 Uiso 1 1 calc R . .
H15C H 0.0514 0.3240 0.5141 0.031 Uiso 1 1 calc R . .
C16 C 0.19303(14) 0.28428(12) 0.42766(11) 0.0240(4) Uani 1 1 d . . .
H16A H 0.2271 0.2896 0.3829 0.036 Uiso 1 1 calc R . .
H16B H 0.1389 0.2456 0.4216 0.036 Uiso 1 1 calc R . .
H16C H 0.2357 0.2609 0.4636 0.036 Uiso 1 1 calc R . .
C17 C 0.26204(13) 0.63667(12) 0.64411(9) 0.0173(4) Uani 1 1 d . . .
C18 C 0.35622(14) 0.66023(12) 0.63497(10) 0.0201(4) Uani 1 1 d . . .
F18 F 0.41080(8) 0.61990(7) 0.58659(6) 0.0267(3) Uani 1 1 d . . .
C19 C 0.40037(14) 0.72564(12) 0.67242(11) 0.0233(4) Uani 1 1 d . . .
F19 F 0.49232(8) 0.74363(8) 0.66155(7) 0.0342(3) Uani 1 1 d . . .
C20 C 0.34942(15) 0.77169(12) 0.72090(10) 0.0238(4) Uani 1 1 d . . .
F20 F 0.39153(9) 0.83236(7) 0.76022(6) 0.0339(3) Uani 1 1 d . . .
C21 C 0.25417(15) 0.75509(13) 0.72857(10) 0.0226(4) Uani 1 1 d . . .
F21 F 0.20289(9) 0.80156(7) 0.77467(6) 0.0308(3) Uani 1 1 d . . .
C22 C 0.21263(14) 0.69026(12) 0.69022(10) 0.0195(4) Uani 1 1 d . . .
F22 F 0.11880(8) 0.68052(7) 0.69995(6) 0.0247(3) 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 C17 1.627(3) . ?
B1 C1 1.636(3) . ?
B1 Cl2 1.894(2) . ?
B1 Cl1 1.928(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.410(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C6 N7 1.491(2) . ?
N7 C8 1.571(2) . ?
N7 C12 1.574(2) . ?
N7 H7 0.895(15) . ?
C8 C15 1.525(3) . ?
C8 C16 1.526(3) . ?
C8 C9 1.532(2) . ?
C9 C10 1.520(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.533(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(3) . ?
C12 C14 1.527(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.391(3) . ?
C17 C22 1.396(3) . ?
C18 F18 1.354(2) . ?
C18 C19 1.389(3) . ?
C19 F19 1.344(2) . ?
C19 C20 1.371(3) . ?
C20 F20 1.343(2) . ?
C20 C21 1.378(3) . ?
C21 F21 1.347(2) . ?
C21 C22 1.376(3) . ?
C22 F22 1.347(2) . ?

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
C17 B1 C1 115.02(15) . . ?
C17 B1 Cl2 109.99(12) . . ?
C1 B1 Cl2 103.73(12) . . ?
C17 B1 Cl1 104.70(12) . . ?
C1 B1 Cl1 115.96(13) . . ?
Cl2 B1 Cl1 107.22(10) . . ?
C6 C1 C2 114.61(16) . . ?
C6 C1 B1 132.52(16) . . ?
C2 C1 B1 112.54(15) . . ?
C3 C2 C1 123.73(18) . . ?
C3 C2 H2 118.1 . . ?
C1 C2 H2 118.1 . . ?
C2 C3 C4 119.64(17) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.36(17) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 119.98(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 122.67(16) . . ?
C5 C6 N7 117.79(16) . . ?
C1 C6 N7 119.52(15) . . ?
C6 N7 C8 114.75(13) . . ?
C6 N7 C12 115.21(13) . . ?
C8 N7 C12 118.13(13) . . ?
C6 N7 H7 103.0(13) . . ?
C8 N7 H7 101.3(13) . . ?
C12 N7 H7 100.7(13) . . ?
C15 C8 C16 108.67(16) . . ?
C15 C8 C9 109.24(15) . . ?
C16 C8 C9 112.02(15) . . ?
C15 C8 N7 106.56(14) . . ?
C16 C8 N7 114.46(14) . . ?
C9 C8 N7 105.66(14) . . ?
C10 C9 C8 114.22(15) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 110.18(15) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 113.77(15) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C14 108.29(15) . . ?
C13 C12 C11 111.68(15) . . ?
C14 C12 C11 110.03(15) . . ?
C13 C12 N7 114.81(15) . . ?
C14 C12 N7 106.19(14) . . ?
C11 C12 N7 105.66(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 113.52(17) . . ?
C18 C17 B1 123.23(16) . . ?
C22 C17 B1 123.25(17) . . ?
F18 C18 C19 115.57(17) . . ?
F18 C18 C17 120.48(17) . . ?
C19 C18 C17 123.94(18) . . ?
F19 C19 C20 120.09(18) . . ?
F19 C19 C18 120.49(18) . . ?
C20 C19 C18 119.43(18) . . ?
F20 C20 C19 120.59(19) . . ?
F20 C20 C21 120.36(18) . . ?
C19 C20 C21 119.05(18) . . ?
F21 C21 C22 120.58(18) . . ?
F21 C21 C20 119.55(18) . . ?
C22 C21 C20 119.86(18) . . ?
F22 C22 C21 115.43(17) . . ?
F22 C22 C17 120.72(17) . . ?
C21 C22 C17 123.85(19) . . ?

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
C17 B1 C1 C6 -137.91(19) . . . . ?
Cl2 B1 C1 C6 101.9(2) . . . . ?
Cl1 B1 C1 C6 -15.3(3) . . . . ?
C17 B1 C1 C2 49.1(2) . . . . ?
Cl2 B1 C1 C2 -71.05(16) . . . . ?
Cl1 B1 C1 C2 171.69(13) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
B1 C1 C2 C3 174.30(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 N7 -178.12(16) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
B1 C1 C6 C5 -172.92(18) . . . . ?
C2 C1 C6 N7 178.25(15) . . . . ?
B1 C1 C6 N7 5.4(3) . . . . ?
C5 C6 N7 C8 70.99(19) . . . . ?
C1 C6 N7 C8 -107.38(18) . . . . ?
C5 C6 N7 C12 -71.28(19) . . . . ?
C1 C6 N7 C12 110.35(17) . . . . ?
C6 N7 C8 C15 49.96(19) . . . . ?
C12 N7 C8 C15 -168.93(14) . . . . ?
C6 N7 C8 C16 -70.17(19) . . . . ?
C12 N7 C8 C16 70.9(2) . . . . ?
C6 N7 C8 C9 166.09(14) . . . . ?
C12 N7 C8 C9 -52.80(18) . . . . ?
C15 C8 C9 C10 167.79(16) . . . . ?
C16 C8 C9 C10 -71.8(2) . . . . ?
N7 C8 C9 C10 53.50(19) . . . . ?
C8 C9 C10 C11 -59.1(2) . . . . ?
C9 C10 C11 C12 59.4(2) . . . . ?
C10 C11 C12 C13 71.3(2) . . . . ?
C10 C11 C12 C14 -168.40(15) . . . . ?
C10 C11 C12 N7 -54.17(19) . . . . ?
C6 N7 C12 C13 70.68(19) . . . . ?
C8 N7 C12 C13 -70.3(2) . . . . ?
C6 N7 C12 C14 -48.94(19) . . . . ?
C8 N7 C12 C14 170.12(14) . . . . ?
C6 N7 C12 C11 -165.80(14) . . . . ?
C8 N7 C12 C11 53.26(18) . . . . ?
C1 B1 C17 C18 27.3(2) . . . . ?
Cl2 B1 C17 C18 143.96(16) . . . . ?
Cl1 B1 C17 C18 -101.13(18) . . . . ?
C1 B1 C17 C22 -151.79(17) . . . . ?
Cl2 B1 C17 C22 -35.1(2) . . . . ?
Cl1 B1 C17 C22 79.76(19) . . . . ?
C22 C17 C18 F18 -173.36(16) . . . . ?
B1 C17 C18 F18 7.5(3) . . . . ?
C22 C17 C18 C19 5.6(3) . . . . ?
B1 C17 C18 C19 -173.62(17) . . . . ?
F18 C18 C19 F19 -2.3(3) . . . . ?
C17 C18 C19 F19 178.74(17) . . . . ?
F18 C18 C19 C20 177.95(17) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
F19 C19 C20 F20 -3.0(3) . . . . ?
C18 C19 C20 F20 176.72(17) . . . . ?
F19 C19 C20 C21 176.71(17) . . . . ?
C18 C19 C20 C21 -3.5(3) . . . . ?
F20 C20 C21 F21 1.6(3) . . . . ?
C19 C20 C21 F21 -178.19(17) . . . . ?
F20 C20 C21 C22 -177.17(16) . . . . ?
C19 C20 C21 C22 3.1(3) . . . . ?
F21 C21 C22 F22 3.0(3) . . . . ?
C20 C21 C22 F22 -178.29(16) . . . . ?
F21 C21 C22 C17 -176.72(17) . . . . ?
C20 C21 C22 C17 2.0(3) . . . . ?
C18 C17 C22 F22 174.25(16) . . . . ?
B1 C17 C22 F22 -6.6(3) . . . . ?
C18 C17 C22 C21 -6.1(3) . . . . ?
B1 C17 C22 C21 173.13(17) . . . . ?

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
N7 H7 Cl1 0.895(15) 2.209(15) 3.0864(15) 166.8(17) .
C14 H14A Cl1 0.98 2.82 3.629(2) 140.2 .
C15 H15A Cl1 0.98 2.97 3.751(2) 137.8 .
C15 H15A Cl2 0.98 2.86 3.524(2) 125.8 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_les106_t_compound_2c
_database_code_depnum_ccdc_archive 'CCDC 1511243'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'8,8-dichloro-7,7-dimethyl-7-aza-8-borabicyclo[4.2.0]octa- 1,3,5-trien-7-ium-8-uide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 B Cl2 N'
_chemical_formula_sum            'C8 H10 B Cl2 N'
_chemical_formula_weight         201.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.838(1)
_cell_length_b                   8.394(1)
_cell_length_c                   8.943(1)
_cell_angle_alpha                85.04(1)
_cell_angle_beta                 80.45(1)
_cell_angle_gamma                69.04(1)
_cell_volume                     472.50(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    120
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.627
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7660
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 dx = 35 mm, 30 sec./deg., 2 deg., 5 sets, 234 frames,
 2348 refl. postref.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in φ and ω, 2°'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6082
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2157
_reflns_number_gt                1810
_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       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0576P)²+0.1752P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2157
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.61601(8) 0.10725(6) 0.15910(6) 0.02504(18) Uani 1 1 d . . . . .
Cl2 Cl 0.52084(8) 0.26439(6) 0.46609(6) 0.02318(17) Uani 1 1 d . . . . .
B1 B 0.4160(4) 0.2607(3) 0.2904(3) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.2715(3) 0.4358(2) 0.2216(2) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.2508(3) 0.5944(3) 0.1507(2) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.3686 0.6313 0.1250 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0506(4) 0.6963(3) 0.1191(2) 0.0202(4) Uani 1 1 d . . . . .
H3 H 0.0318 0.8054 0.0716 0.024 Uiso 1 1 calc R U . . .
C4 C -0.1233(3) 0.6433(3) 0.1549(2) 0.0196(4) Uani 1 1 d . . . . .
H4 H -0.2569 0.7169 0.1306 0.024 Uiso 1 1 calc R U . . .
C5 C -0.1061(3) 0.4847(3) 0.2257(2) 0.0182(4) Uani 1 1 d . . . . .
H5 H -0.2227 0.4464 0.2517 0.022 Uiso 1 1 calc R U . . .
C6 C 0.0957(3) 0.3887(2) 0.2544(2) 0.0156(4) Uani 1 1 d . . . . .
N7 N 0.1855(3) 0.2183(2) 0.32781(18) 0.0150(4) Uani 1 1 d . . . . .
C8 C 0.0922(3) 0.2108(3) 0.4894(2) 0.0196(4) Uani 1 1 d . . . . .
H8A H 0.0900 0.3098 0.5412 0.029 Uiso 1 1 calc R U . . .
H8B H 0.1776 0.1057 0.5385 0.029 Uiso 1 1 calc R U . . .
H8C H -0.0527 0.2119 0.4953 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1704(4) 0.0772(3) 0.2454(2) 0.0202(4) Uani 1 1 d . . . . .
H9A H 0.0224 0.0845 0.2573 0.030 Uiso 1 1 calc R U . . .
H9B H 0.2559 -0.0328 0.2872 0.030 Uiso 1 1 calc R U . . .
H9C H 0.2231 0.0871 0.1374 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 1.838(2) . ?
Cl2 B1 1.839(2) . ?
B1 C1 1.588(3) . ?
B1 N7 1.711(3) . ?
C1 C6 1.375(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 N7 1.482(2) . ?
N7 C8 1.486(3) . ?
N7 C9 1.490(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 N7 83.79(14) . . ?
C1 B1 Cl1 118.12(15) . . ?
N7 B1 Cl1 111.55(14) . . ?
C1 B1 Cl2 118.59(15) . . ?
N7 B1 Cl2 111.29(14) . . ?
Cl1 B1 Cl2 110.46(12) . . ?
C6 C1 C2 118.68(18) . . ?
C6 C1 B1 91.77(16) . . ?
C2 C1 B1 149.5(2) . . ?
C3 C2 C1 117.22(19) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 122.08(19) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 121.65(19) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 113.94(19) . . ?
C6 C5 H5 123.0 . . ?
C4 C5 H5 123.0 . . ?
C1 C6 C5 126.41(18) . . ?
C1 C6 N7 100.98(16) . . ?
C5 C6 N7 132.58(19) . . ?
C6 N7 C8 112.83(15) . . ?
C6 N7 C9 113.40(15) . . ?
C8 N7 C9 109.61(16) . . ?
C6 N7 B1 83.44(14) . . ?
C8 N7 B1 117.37(15) . . ?
C9 N7 B1 117.93(15) . . ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N7 C9 H9A 109.5 . . ?
N7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 B1 C1 C6 -0.82(14) . . . . ?
Cl1 B1 C1 C6 110.34(17) . . . . ?
Cl2 B1 C1 C6 -111.72(17) . . . . ?
N7 B1 C1 C2 180.0(3) . . . . ?
Cl1 B1 C1 C2 -68.9(4) . . . . ?
Cl2 B1 C1 C2 69.1(4) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
B1 C1 C2 C3 179.8(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
B1 C1 C6 C5 179.7(2) . . . . ?
C2 C1 C6 N7 -179.51(17) . . . . ?
B1 C1 C6 N7 0.95(16) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 N7 178.91(19) . . . . ?
C1 C6 N7 C8 116.09(18) . . . . ?
C5 C6 N7 C8 -62.5(3) . . . . ?
C1 C6 N7 C9 -118.53(18) . . . . ?
C5 C6 N7 C9 62.9(3) . . . . ?
C1 C6 N7 B1 -0.89(15) . . . . ?
C5 C6 N7 B1 -179.5(2) . . . . ?
C1 B1 N7 C6 0.76(13) . . . . ?
Cl1 B1 N7 C6 -117.06(14) . . . . ?
Cl2 B1 N7 C6 119.07(14) . . . . ?
C1 B1 N7 C8 -111.59(17) . . . . ?
Cl1 B1 N7 C8 130.58(15) . . . . ?
Cl2 B1 N7 C8 6.7(2) . . . . ?
C1 B1 N7 C9 113.81(17) . . . . ?
Cl1 B1 N7 C9 -4.0(2) . . . . ?
Cl2 B1 N7 C9 -127.88(16) . . . . ?

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
C8 H8C Cl2 0.98 2.84 3.809(2) 168.8 1_455

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_les101_f_compound_10c
_database_code_depnum_ccdc_archive 'CCDC 912585'
_audit_update_record             
;
2012-11-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
#TrackingRef 'kosta_Angew_2012.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
trichloro(2-(2,2,6,6-tetramethylpiperidin-1-ium-1-yl)phenyl)borate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 B Cl3 N'
_chemical_formula_sum            'C15 H23 B Cl3 N'
_chemical_formula_weight         334.50

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'

loop_
_symmetry_equiv_pos_as_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                   7.867(1)
_cell_length_b                   15.592(2)
_cell_length_c                   14.279(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.89(2)
_cell_angle_gamma                90.00
_cell_volume                     1692.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    497
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8574
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
dx = 35 mm, 70 sec./deg., 2 deg., 9 sets, 391 frames,
7950 refl. postrefinement
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18128
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3894
_reflns_number_gt                3675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.4400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_number_reflns         3894
_refine_ls_number_parameters     184
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0292(3) 0.47732(16) 0.51994(17) 0.0208(5) Uani 1 1 d . . .
Cl1 Cl 0.03479(6) 0.49030(3) 0.65299(4) 0.02303(12) Uani 1 1 d . . .
Cl2 Cl -0.19173(7) 0.43032(4) 0.46076(4) 0.03501(15) Uani 1 1 d . . .
Cl3 Cl 0.04245(9) 0.58799(4) 0.47270(5) 0.03982(17) Uani 1 1 d . . .
C1 C 0.1791(3) 0.41697(12) 0.49390(14) 0.0176(4) Uani 1 1 d . . .
C2 C 0.1762(3) 0.41824(14) 0.39487(15) 0.0216(4) Uani 1 1 d . . .
H2 H 0.0949 0.4553 0.3530 0.026 Uiso 1 1 calc R . .
C3 C 0.2860(3) 0.36814(15) 0.35526(16) 0.0238(4) Uani 1 1 d . . .
H3 H 0.2811 0.3723 0.2882 0.029 Uiso 1 1 calc R . .
C4 C 0.4020(3) 0.31241(15) 0.41391(17) 0.0248(5) Uani 1 1 d . . .
H4 H 0.4754 0.2767 0.3871 0.030 Uiso 1 1 calc R . .
C5 C 0.4116(3) 0.30850(14) 0.51195(16) 0.0211(4) Uani 1 1 d . . .
H5 H 0.4920 0.2703 0.5525 0.025 Uiso 1 1 calc R . .
C6 C 0.3035(3) 0.36061(13) 0.55120(14) 0.0164(4) Uani 1 1 d . . .
N7 N 0.3246(2) 0.35704(11) 0.65732(12) 0.0159(3) Uani 1 1 d D . .
H7 H 0.244(3) 0.3930(15) 0.6667(18) 0.019 Uiso 1 1 d D . .
C8 C 0.4997(3) 0.39909(15) 0.71954(16) 0.0224(4) Uani 1 1 d . . .
C9 C 0.4780(3) 0.40631(16) 0.82265(17) 0.0296(5) Uani 1 1 d . . .
H9A H 0.5893 0.4279 0.8656 0.036 Uiso 1 1 calc R . .
H9B H 0.3852 0.4491 0.8231 0.036 Uiso 1 1 calc R . .
C10 C 0.4300(3) 0.32236(17) 0.86371(17) 0.0313(5) Uani 1 1 d . . .
H10A H 0.5241 0.2796 0.8663 0.038 Uiso 1 1 calc R . .
H10B H 0.4191 0.3317 0.9305 0.038 Uiso 1 1 calc R . .
C11 C 0.2573(3) 0.28869(16) 0.80067(16) 0.0253(5) Uani 1 1 d . . .
H11A H 0.1635 0.3306 0.8020 0.030 Uiso 1 1 calc R . .
H11B H 0.2281 0.2346 0.8292 0.030 Uiso 1 1 calc R . .
C12 C 0.2565(3) 0.27189(13) 0.69471(15) 0.0193(4) Uani 1 1 d . . .
C13 C 0.0665(3) 0.25950(15) 0.63433(18) 0.0261(5) Uani 1 1 d . . .
H13A H -0.0030 0.3104 0.6405 0.039 Uiso 1 1 calc R . .
H13B H 0.0156 0.2090 0.6578 0.039 Uiso 1 1 calc R . .
H13C H 0.0654 0.2512 0.5661 0.039 Uiso 1 1 calc R . .
C14 C 0.3624(3) 0.19258(15) 0.68443(19) 0.0272(5) Uani 1 1 d . . .
H14A H 0.4841 0.1998 0.7229 0.041 Uiso 1 1 calc R . .
H14B H 0.3609 0.1845 0.6161 0.041 Uiso 1 1 calc R . .
H14C H 0.3107 0.1422 0.7076 0.041 Uiso 1 1 calc R . .
C15 C 0.5106(3) 0.48827(15) 0.67723(19) 0.0298(5) Uani 1 1 d . . .
H15A H 0.5241 0.4828 0.6111 0.045 Uiso 1 1 calc R . .
H15B H 0.6120 0.5190 0.7174 0.045 Uiso 1 1 calc R . .
H15C H 0.4027 0.5202 0.6759 0.045 Uiso 1 1 calc R . .
C16 C 0.6671(3) 0.34982(17) 0.71751(19) 0.0289(5) Uani 1 1 d . . .
H16A H 0.6769 0.3459 0.6506 0.043 Uiso 1 1 calc R . .
H16B H 0.6616 0.2920 0.7435 0.043 Uiso 1 1 calc R . .
H16C H 0.7698 0.3800 0.7572 0.043 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C1 1.625(3) . ?
B1 Cl3 1.865(2) . ?
B1 Cl2 1.875(3) . ?
B1 Cl1 1.900(2) . ?
C1 C2 1.408(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 N7 1.482(3) . ?
N7 C12 1.575(3) . ?
N7 C8 1.578(3) . ?
N7 H7 0.883(16) . ?
C8 C15 1.527(3) . ?
C8 C9 1.529(3) . ?
C8 C16 1.531(3) . ?
C9 C10 1.521(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.534(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.519(3) . ?
C12 C13 1.534(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 Cl3 109.98(15) . . ?
C1 B1 Cl2 108.29(15) . . ?
Cl3 B1 Cl2 109.27(12) . . ?
C1 B1 Cl1 117.32(15) . . ?
Cl3 B1 Cl1 105.90(12) . . ?
Cl2 B1 Cl1 105.83(12) . . ?
C2 C1 C6 114.92(18) . . ?
C2 C1 B1 113.32(18) . . ?
C6 C1 B1 131.65(18) . . ?
C3 C2 C1 123.3(2) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 122.30(19) . . ?
C5 C6 N7 118.02(18) . . ?
C1 C6 N7 119.68(17) . . ?
C6 N7 C12 114.82(15) . . ?
C6 N7 C8 114.33(15) . . ?
C12 N7 C8 118.90(15) . . ?
C6 N7 H7 103.6(16) . . ?
C12 N7 H7 99.4(17) . . ?
C8 N7 H7 102.0(17) . . ?
C15 C8 C9 110.2(2) . . ?
C15 C8 C16 108.27(19) . . ?
C9 C8 C16 111.39(19) . . ?
C15 C8 N7 106.57(17) . . ?
C9 C8 N7 105.97(17) . . ?
C16 C8 N7 114.31(18) . . ?
C10 C9 C8 114.1(2) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 110.00(19) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C12 114.88(18) . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C14 C12 C11 111.78(18) . . ?
C14 C12 C13 108.83(18) . . ?
C11 C12 C13 109.42(17) . . ?
C14 C12 N7 114.23(16) . . ?
C11 C12 N7 105.94(17) . . ?
C13 C12 N7 106.42(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl3 B1 C1 C2 -52.7(2) . . . . ?
Cl2 B1 C1 C2 66.7(2) . . . . ?
Cl1 B1 C1 C2 -173.73(16) . . . . ?
Cl3 B1 C1 C6 131.4(2) . . . . ?
Cl2 B1 C1 C6 -109.3(2) . . . . ?
Cl1 B1 C1 C6 10.3(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
B1 C1 C2 C3 -176.5(2) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 N7 -177.19(19) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
B1 C1 C6 C5 174.2(2) . . . . ?
C2 C1 C6 N7 177.01(18) . . . . ?
B1 C1 C6 N7 -7.1(3) . . . . ?
C5 C6 N7 C12 -71.3(2) . . . . ?
C1 C6 N7 C12 109.9(2) . . . . ?
C5 C6 N7 C8 71.2(2) . . . . ?
C1 C6 N7 C8 -107.6(2) . . . . ?
C6 N7 C8 C15 50.7(2) . . . . ?
C12 N7 C8 C15 -168.44(18) . . . . ?
C6 N7 C8 C9 168.08(17) . . . . ?
C12 N7 C8 C9 -51.1(2) . . . . ?
C6 N7 C8 C16 -68.9(2) . . . . ?
C12 N7 C8 C16 72.0(2) . . . . ?
C15 C8 C9 C10 168.6(2) . . . . ?
C16 C8 C9 C10 -71.2(3) . . . . ?
N7 C8 C9 C10 53.7(2) . . . . ?
C8 C9 C10 C11 -59.8(3) . . . . ?
C9 C10 C11 C12 59.0(3) . . . . ?
C10 C11 C12 C14 73.0(3) . . . . ?
C10 C11 C12 C13 -166.41(19) . . . . ?
C10 C11 C12 N7 -52.0(2) . . . . ?
C6 N7 C12 C14 67.2(2) . . . . ?
C8 N7 C12 C14 -73.5(2) . . . . ?
C6 N7 C12 C11 -169.30(16) . . . . ?
C8 N7 C12 C11 50.0(2) . . . . ?
C6 N7 C12 C13 -52.9(2) . . . . ?
C8 N7 C12 C13 166.41(17) . . . . ?

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
N7 H7 Cl1 0.883(16) 2.209(18) 3.0735(18) 166(2) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.053

#==============================================================================
# _eof # End of Crystallographic Information File



