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

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

data_test_a
_database_code_depnum_ccdc_archive 'CCDC 1842548'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of W?rzburg
Germany
;
_audit_update_record             
;
2018-05-10 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT410_test_a              
;
PROBLEM: Short Intra H...H Contact  H12B     ..H16A             1.73 Ang.
RESPONSE: One of the butyl groups of the cation is disordered over two positions. The short contact is due to the short distance between H atoms of the two different, disordered chains.
;


#=================================================================
#DATA 1
#=================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H39 B F5 N'
_chemical_formula_weight         375.31

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'

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

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

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

_cell_length_a                   8.8965(16)
_cell_length_b                   16.170(3)
_cell_length_c                   15.312(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.429(6)
_cell_angle_gamma                90
_cell_volume                     2178.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.5005
_cell_measurement_theta_max      26.1185

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6491
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27674
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         26.218
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4355
_reflns_number_gt                3549
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0510P)²+1.3061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1A N 0.60362(14) 0.62990(8) 0.69489(8) 0.0239(3) Uani 0.870(3) 1 d . . P A 1
C15A C 0.76512(19) 0.60222(14) 0.69361(12) 0.0213(4) Uani 0.870(3) 1 d . . P A
1
H25A H 0.8332 0.6351 0.7374 0.026 Uiso 0.870(3) 1 calc R U P A 1
H25B H 0.7930 0.6141 0.6346 0.026 Uiso 0.870(3) 1 calc R U P A 1
C16A C 0.79195(19) 0.51126(11) 0.71384(12) 0.0248(4) Uani 0.870(3) 1 d . . P A
1
H26A H 0.7200 0.4778 0.6728 0.030 Uiso 0.870(3) 1 calc R U P A 1
H26B H 0.7727 0.4997 0.7747 0.030 Uiso 0.870(3) 1 calc R U P A 1
C17A C 0.9543(2) 0.48664(14) 0.70478(13) 0.0278(5) Uani 0.870(3) 1 d . . P A 1
H27A H 0.9639 0.4258 0.7108 0.033 Uiso 0.870(3) 1 calc R U P A 1
H27B H 0.9740 0.5014 0.6447 0.033 Uiso 0.870(3) 1 calc R U P A 1
C28A C 1.0745(4) 0.52674(16) 0.7715(2) 0.0410(6) Uani 0.870(3) 1 d . . P A 1
H28A H 1.1744 0.5040 0.7651 0.062 Uiso 0.870(3) 1 calc R U P A 1
H28B H 1.0523 0.5157 0.8312 0.062 Uiso 0.870(3) 1 calc R U P A 1
H28C H 1.0746 0.5866 0.7613 0.062 Uiso 0.870(3) 1 calc R U P A 1
N1B N 0.60362(14) 0.62990(8) 0.69489(8) 0.0239(3) Uani 0.130(3) 1 d . . P A 2
C15B C 0.7463(15) 0.5607(10) 0.6854(9) 0.0213(4) Uani 0.130(3) 1 d . . P A 2
H15A H 0.7046 0.5039 0.6855 0.026 Uiso 0.130(3) 1 calc R U P A 2
H15B H 0.7825 0.5694 0.6280 0.026 Uiso 0.130(3) 1 calc R U P A 2
C16B C 0.8768(13) 0.5675(7) 0.7566(7) 0.022(3) Uani 0.130(3) 1 d . . P A 2
H16A H 0.8494 0.5448 0.8122 0.027 Uiso 0.130(3) 1 calc R U P A 2
H16B H 0.9051 0.6264 0.7665 0.027 Uiso 0.130(3) 1 calc R U P A 2
C17B C 1.010(2) 0.5194(11) 0.7297(12) 0.0278(5) Uani 0.130(3) 1 d . . P A 2
H17A H 0.9796 0.4609 0.7193 0.033 Uiso 0.130(3) 1 calc R U P A 2
H17B H 1.0350 0.5421 0.6736 0.033 Uiso 0.130(3) 1 calc R U P A 2
C18B C 1.150(2) 0.5228(9) 0.7987(12) 0.034(3) Uani 0.130(3) 1 d . . P A 2
H18A H 1.2306 0.4886 0.7796 0.051 Uiso 0.130(3) 1 calc R U P A 2
H18B H 1.1259 0.5018 0.8550 0.051 Uiso 0.130(3) 1 calc R U P A 2
H18C H 1.1857 0.5801 0.8062 0.051 Uiso 0.130(3) 1 calc R U P A 2
F1 F -0.47171(13) 0.60062(6) 0.24586(7) 0.0433(3) Uani 1 1 d . . . . .
H1 H -0.553(2) 0.7450(13) 0.3933(13) 0.044(5) Uiso 1 1 d . . . . .
C1 C -0.46172(17) 0.67711(9) 0.28740(10) 0.0245(3) Uani 1 1 d . . . . .
B1 B -0.5631(2) 0.68292(13) 0.36504(13) 0.0310(4) Uani 1 1 d . . . . .
C2 C -0.29263(19) 0.69100(11) 0.31032(12) 0.0344(4) Uani 1 1 d . . . . .
H2 H -0.516(2) 0.6328(12) 0.4145(12) 0.036(5) Uiso 1 1 d . . . . .
F2 F -0.50439(12) 0.73223(7) 0.21925(7) 0.0423(3) Uani 1 1 d . . . . .
F3 F -0.21811(13) 0.68300(8) 0.24067(8) 0.0535(3) Uani 1 1 d . . . . .
H3 H -0.683(2) 0.6682(12) 0.3353(13) 0.044(5) Uiso 1 1 d . . . . .
C3 C 0.60416(19) 0.72328(10) 0.68828(10) 0.0273(3) Uani 1 1 d . . . . .
F4 F -0.23073(13) 0.63723(9) 0.36993(9) 0.0634(4) Uani 1 1 d . . . . .
H11B H 0.448(2) 0.6290(12) 0.7766(13) 0.040(5) Uiso 1 1 d . . . . .
C4 C 0.64710(18) 0.75921(10) 0.60387(10) 0.0290(4) Uani 1 1 d . . . . .
H4A H 0.7543 0.7459 0.5993 0.035 Uiso 1 1 calc R U . . .
H4B H 0.5819 0.7353 0.5520 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6596(3) 0.89532(13) 0.52402(14) 0.0532(6) Uani 1 1 d . . . . .
H6A H 0.5930 0.8736 0.4724 0.080 Uiso 1 1 calc R U . . .
H6B H 0.7659 0.8858 0.5169 0.080 Uiso 1 1 calc R U . . .
H6C H 0.6418 0.9548 0.5293 0.080 Uiso 1 1 calc R U . . .
H7B H 0.5474(18) 0.5941(10) 0.5674(11) 0.020(4) Uiso 1 1 d . . . . .
F5 F -0.26233(14) 0.76652(8) 0.34208(10) 0.0623(4) Uani 1 1 d . . . . .
H11A H 0.5407(17) 0.5495(11) 0.7786(10) 0.012(4) Uiso 1 1 d . . . . .
C5 C 0.6257(2) 0.85200(11) 0.60593(11) 0.0368(4) Uani 1 1 d . . . . .
H5A H 0.5194 0.8640 0.6139 0.044 Uiso 1 1 calc R U . . .
H5B H 0.6928 0.8748 0.6576 0.044 Uiso 1 1 calc R U . . .
C7 C 0.49670(17) 0.59149(10) 0.61909(10) 0.0241(3) Uani 1 1 d . . . . .
H7A H 0.4881(19) 0.5356(11) 0.6333(11) 0.023(4) Uiso 1 1 d . . . . .
C9 C 0.23007(18) 0.57748(10) 0.54195(10) 0.0301(4) Uani 1 1 d . . . . .
H9A H 0.2124 0.5259 0.5738 0.036 Uiso 1 1 calc R U . . .
H9B H 0.2737 0.5623 0.4883 0.036 Uiso 1 1 calc R U . . .
H3A H 0.503(2) 0.7397(11) 0.6982(11) 0.024(4) Uiso 1 1 d . . . . .
C8 C 0.34165(17) 0.63178(10) 0.60061(10) 0.0254(3) Uani 1 1 d . . . . .
H8A H 0.3507 0.6858 0.5714 0.031 Uiso 1 1 calc R U . . .
H8B H 0.3030 0.6420 0.6571 0.031 Uiso 1 1 calc R U . . .
H3B H 0.675(2) 0.7426(11) 0.7383(12) 0.028(4) Uiso 1 1 d . . . . .
C10 C 0.0800(2) 0.62198(12) 0.51559(13) 0.0413(5) Uani 1 1 d . . . . .
H10A H 0.0942 0.6674 0.4752 0.062 Uiso 1 1 calc R U . . .
H10B H 0.0443 0.6443 0.5684 0.062 Uiso 1 1 calc R U . . .
H10C H 0.0046 0.5830 0.4862 0.062 Uiso 1 1 calc R U . . .
C11 C 0.54743(18) 0.60531(12) 0.78022(10) 0.0275(4) Uani 1 1 d . . . . .
C12 C 0.6413(2) 0.63328(11) 0.86488(10) 0.0314(4) Uani 1 1 d . . . . .
H12A H 0.6443 0.6945 0.8671 0.038 Uiso 1 1 calc R U . . .
H12B H 0.7467 0.6127 0.8677 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5719(2) 0.60011(14) 0.94238(11) 0.0420(5) Uani 1 1 d . . . . .
H13A H 0.4672 0.6218 0.9392 0.050 Uiso 1 1 calc R U . . .
H13B H 0.5655 0.5391 0.9379 0.050 Uiso 1 1 calc R U . . .
C14 C 0.6612(3) 0.62311(13) 1.03069(12) 0.0528(6) Uani 1 1 d . . . . .
H14A H 0.7628 0.5985 1.0361 0.079 Uiso 1 1 calc R U . . .
H14B H 0.6085 0.6023 1.0781 0.079 Uiso 1 1 calc R U . . .
H14C H 0.6701 0.6834 1.0351 0.079 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
N1A C15A 1.508(2) . ?
N1A C3 1.513(2) . ?
N1A C11 1.5189(19) . ?
N1A C7 1.5212(19) . ?
C15A C16A 1.515(3) . ?
C15A H25A 0.9900 . ?
C15A H25B 0.9900 . ?
C16A C17A 1.524(2) . ?
C16A H26A 0.9900 . ?
C16A H26B 0.9900 . ?
C17A C28A 1.512(3) . ?
C17A H27A 0.9900 . ?
C17A H27B 0.9900 . ?
C28A H28A 0.9800 . ?
C28A H28B 0.9800 . ?
C28A H28C 0.9800 . ?
N1B C3 1.513(2) . ?
N1B C11 1.5189(19) . ?
N1B C7 1.5212(19) . ?
N1B C15B 1.715(14) . ?
C15B C16B 1.475(18) . ?
C15B H15A 0.9900 . ?
C15B H15B 0.9900 . ?
C16B C17B 1.525(17) . ?
C16B H16A 0.9900 . ?
C16B H16B 0.9900 . ?
C17B C18B 1.51(3) . ?
C17B H17A 0.9900 . ?
C17B H17B 0.9900 . ?
C18B H18A 0.9800 . ?
C18B H18B 0.9800 . ?
C18B H18C 0.9800 . ?
F1 C1 1.3878(18) . ?
C1 F2 1.3824(17) . ?
C1 C2 1.511(2) . ?
C1 B1 1.597(2) . ?
B1 H1 1.09(2) . ?
B1 H2 1.145(19) . ?
B1 H3 1.12(2) . ?
C2 F4 1.321(2) . ?
C2 F5 1.327(2) . ?
C2 F3 1.342(2) . ?
C3 C4 1.516(2) . ?
C3 H3A 0.974(18) . ?
C3 H3B 0.968(18) . ?
C4 C5 1.513(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C5 1.505(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.514(2) . ?
C7 H7B 0.968(17) . ?
C7 H7A 0.936(18) . ?
C9 C8 1.517(2) . ?
C9 C10 1.518(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.505(2) . ?
C11 H11B 0.96(2) . ?
C11 H11A 0.904(17) . ?
C12 C13 1.514(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.511(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C15A N1A C3 106.44(13) . . ?
C15A N1A C11 111.58(12) . . ?
C3 N1A C11 108.87(12) . . ?
C15A N1A C7 111.06(12) . . ?
C3 N1A C7 111.35(12) . . ?
C11 N1A C7 107.55(12) . . ?
N1A C15A C16A 114.05(15) . . ?
N1A C15A H25A 108.7 . . ?
C16A C15A H25A 108.7 . . ?
N1A C15A H25B 108.7 . . ?
C16A C15A H25B 108.7 . . ?
H25A C15A H25B 107.6 . . ?
C15A C16A C17A 110.98(15) . . ?
C15A C16A H26A 109.4 . . ?
C17A C16A H26A 109.4 . . ?
C15A C16A H26B 109.4 . . ?
C17A C16A H26B 109.4 . . ?
H26A C16A H26B 108.0 . . ?
C28A C17A C16A 114.35(19) . . ?
C28A C17A H27A 108.7 . . ?
C16A C17A H27A 108.7 . . ?
C28A C17A H27B 108.7 . . ?
C16A C17A H27B 108.7 . . ?
H27A C17A H27B 107.6 . . ?
C17A C28A H28A 109.5 . . ?
C17A C28A H28B 109.5 . . ?
H28A C28A H28B 109.5 . . ?
C17A C28A H28C 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C3 N1B C11 108.87(12) . . ?
C3 N1B C7 111.35(12) . . ?
C11 N1B C7 107.55(12) . . ?
C3 N1B C15B 129.5(5) . . ?
C11 N1B C15B 104.1(5) . . ?
C7 N1B C15B 93.3(5) . . ?
C16B C15B N1B 113.6(10) . . ?
C16B C15B H15A 108.8 . . ?
N1B C15B H15A 108.8 . . ?
C16B C15B H15B 108.8 . . ?
N1B C15B H15B 108.8 . . ?
H15A C15B H15B 107.7 . . ?
C15B C16B C17B 108.7(12) . . ?
C15B C16B H16A 109.9 . . ?
C17B C16B H16A 109.9 . . ?
C15B C16B H16B 109.9 . . ?
C17B C16B H16B 109.9 . . ?
H16A C16B H16B 108.3 . . ?
C18B C17B C16B 112.8(14) . . ?
C18B C17B H17A 109.0 . . ?
C16B C17B H17A 109.0 . . ?
C18B C17B H17B 109.0 . . ?
C16B C17B H17B 109.0 . . ?
H17A C17B H17B 107.8 . . ?
C17B C18B H18A 109.5 . . ?
C17B C18B H18B 109.5 . . ?
H18A C18B H18B 109.5 . . ?
C17B C18B H18C 109.5 . . ?
H18A C18B H18C 109.5 . . ?
H18B C18B H18C 109.5 . . ?
F2 C1 F1 103.69(12) . . ?
F2 C1 C2 103.50(13) . . ?
F1 C1 C2 103.51(13) . . ?
F2 C1 B1 113.67(13) . . ?
F1 C1 B1 112.86(13) . . ?
C2 C1 B1 118.05(14) . . ?
C1 B1 H1 109.1(11) . . ?
C1 B1 H2 104.9(9) . . ?
H1 B1 H2 112.8(14) . . ?
C1 B1 H3 107.0(10) . . ?
H1 B1 H3 111.9(15) . . ?
H2 B1 H3 110.7(14) . . ?
F4 C2 F5 108.10(16) . . ?
F4 C2 F3 106.33(14) . . ?
F5 C2 F3 106.40(14) . . ?
F4 C2 C1 111.27(14) . . ?
F5 C2 C1 111.33(14) . . ?
F3 C2 C1 113.09(15) . . ?
N1B C3 C4 116.30(13) . . ?
N1A C3 C4 116.30(13) . . ?
N1B C3 H3A 104.4(10) . . ?
N1A C3 H3A 104.4(10) . . ?
C4 C3 H3A 112.6(10) . . ?
N1B C3 H3B 106.1(10) . . ?
N1A C3 H3B 106.1(10) . . ?
C4 C3 H3B 109.6(10) . . ?
H3A C3 H3B 107.2(14) . . ?
C5 C4 C3 108.30(13) . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C6 C5 C4 113.76(15) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C8 C7 N1A 114.68(12) . . ?
C8 C7 N1B 114.68(12) . . ?
C8 C7 H7B 110.5(10) . . ?
N1A C7 H7B 106.9(10) . . ?
N1B C7 H7B 106.9(10) . . ?
C8 C7 H7A 110.8(10) . . ?
N1A C7 H7A 106.3(10) . . ?
N1B C7 H7A 106.3(10) . . ?
H7B C7 H7A 107.2(14) . . ?
C8 C9 C10 110.89(14) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C7 C8 C9 111.14(13) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1A 116.82(13) . . ?
C12 C11 N1B 116.82(13) . . ?
C12 C11 H11B 108.7(12) . . ?
N1A C11 H11B 105.3(12) . . ?
N1B C11 H11B 105.3(12) . . ?
C12 C11 H11A 110.5(10) . . ?
N1A C11 H11A 105.4(10) . . ?
N1B C11 H11A 105.4(10) . . ?
H11B C11 H11A 109.9(15) . . ?
C11 C12 C13 109.28(14) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 113.16(17) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_JaRo020_a
_database_code_depnum_ccdc_archive 'CCDC 1842550'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of W?rzburg
Germany
;
_audit_update_record             
;
2018-05-10 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;


#=================================================================
#DATA 1
#================================================================= 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 B F5 N2'
_chemical_formula_sum            'C8 H6 B F5 N2'
_chemical_formula_weight         235.96

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   9.7492(10)
_cell_length_b                   8.9386(9)
_cell_length_c                   22.528(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.546(3)
_cell_angle_gamma                90
_cell_volume                     1959.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3114
_cell_measurement_theta_min      2.4515
_cell_measurement_theta_max      25.9295

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11419
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1922
_reflns_number_gt                1601
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0460P)²+0.9280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1922
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
F1 F 0.05926(9) 0.34989(9) 0.64586(4) 0.0197(2) Uani 1 1 d . . . . .
C1 C 0.06321(15) 0.27142(16) 0.59296(6) 0.0140(3) Uani 1 1 d . . . . .
F2 F 0.11192(9) 0.37428(9) 0.55329(4) 0.0199(2) Uani 1 1 d . . . . .
C2 C -0.08704(15) 0.24774(17) 0.57215(7) 0.0191(3) Uani 1 1 d . . . . .
F3 F -0.09720(9) 0.17679(11) 0.52006(4) 0.0318(3) Uani 1 1 d . . . . .
F4 F -0.15156(9) 0.16585(10) 0.61142(4) 0.0276(3) Uani 1 1 d . . . . .
N11 N 0.30380(12) 0.17833(12) 0.62520(5) 0.0147(3) Uani 1 1 d . . . . .
F5 F -0.15664(9) 0.37656(10) 0.56525(4) 0.0273(3) Uani 1 1 d . . . . .
C11 C 0.39258(15) 0.23986(16) 0.58875(7) 0.0166(3) Uani 1 1 d . . . . .
H11 H 0.3700 0.2404 0.5471 0.020 Uiso 1 1 calc R U . . .
N21 N 0.77170(13) 0.42451(15) 0.71512(6) 0.0228(3) Uani 1 1 d . . . . .
B1 B 0.15609(17) 0.12245(19) 0.59919(8) 0.0179(4) Uani 1 1 d . . . . .
H1 H 0.1678(17) 0.0720(19) 0.5550(8) 0.027 Uiso 1 1 d . U . . .
H2 H 0.1104(17) 0.0416(19) 0.6348(8) 0.027 Uiso 1 1 d . U . . .
C21 C 0.67374(15) 0.36761(16) 0.69533(7) 0.0171(3) Uani 1 1 d . . . . .
C15 C 0.33725(16) 0.17240(16) 0.68391(7) 0.0179(3) Uani 1 1 d . . . . .
H15 H 0.2754 0.1265 0.7093 0.022 Uiso 1 1 calc R U . . .
C14 C 0.45884(15) 0.23107(17) 0.70835(7) 0.0192(3) Uani 1 1 d . . . . .
H14 H 0.4810 0.2252 0.7499 0.023 Uiso 1 1 calc R U . . .
C13 C 0.54825(14) 0.29893(15) 0.67090(7) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.51525(15) 0.30205(16) 0.61007(7) 0.0163(3) Uani 1 1 d . . . . .
H12 H 0.5760 0.3461 0.5837 0.020 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
F1 C1 1.3856(16) . ?
C1 F2 1.3862(16) . ?
C1 C2 1.525(2) . ?
C1 B1 1.612(2) . ?
C2 F3 1.3321(18) . ?
C2 F4 1.3354(18) . ?
C2 F5 1.3407(18) . ?
N11 C15 1.343(2) . ?
N11 C11 1.3467(18) . ?
N11 B1 1.601(2) . ?
C11 C12 1.378(2) . ?
C11 H11 0.9500 . ?
N21 C21 1.1475(19) . ?
B1 H1 1.104(17) . ?
B1 H2 1.188(17) . ?
C21 C13 1.447(2) . ?
C15 C14 1.379(2) . ?
C15 H15 0.9500 . ?
C14 C13 1.389(2) . ?
C14 H14 0.9500 . ?
C13 C12 1.388(2) . ?
C12 H12 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
F1 C1 F2 104.33(11) . . ?
F1 C1 C2 104.92(11) . . ?
F2 C1 C2 104.76(11) . . ?
F1 C1 B1 112.88(12) . . ?
F2 C1 B1 113.02(12) . . ?
C2 C1 B1 115.85(12) . . ?
F3 C2 F4 108.07(12) . . ?
F3 C2 F5 107.30(13) . . ?
F4 C2 F5 106.96(12) . . ?
F3 C2 C1 110.77(12) . . ?
F4 C2 C1 110.81(12) . . ?
F5 C2 C1 112.71(12) . . ?
C15 N11 C11 119.36(13) . . ?
C15 N11 B1 120.41(12) . . ?
C11 N11 B1 120.12(12) . . ?
N11 C11 C12 121.93(14) . . ?
N11 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
N11 B1 C1 105.19(11) . . ?
N11 B1 H1 108.4(9) . . ?
C1 B1 H1 110.4(9) . . ?
N11 B1 H2 108.0(8) . . ?
C1 B1 H2 109.3(8) . . ?
H1 B1 H2 115.1(12) . . ?
N21 C21 C13 178.58(16) . . ?
N11 C15 C14 121.89(14) . . ?
N11 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C14 C13 118.66(14) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C12 C13 C14 119.49(14) . . ?
C12 C13 C21 120.39(14) . . ?
C14 C13 C21 120.12(13) . . ?
C11 C12 C13 118.62(14) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_test_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1842549'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of W?rzburg
Germany
;
_audit_update_record             
;
2018-05-10 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;


#=================================================================
#DATA 1
#================================================================= 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 B F5 P'
_chemical_formula_sum            'C20 H17 B F5 P'
_chemical_formula_weight         394.11

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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                   8.943(3)
_cell_length_b                   10.057(4)
_cell_length_c                   10.567(4)
_cell_angle_alpha                96.064(9)
_cell_angle_beta                 101.313(9)
_cell_angle_gamma                95.583(10)
_cell_volume                     920.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2867
_cell_measurement_theta_min      2.3375
_cell_measurement_theta_max      26.3305

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.184
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6309
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   
; 
The crystal was immersed in a film of perfluoropolyether oil, mounted
on a polyimide microloop (MicroMounts of MiTeGen) and transferred to
stream of cold nitrogen (Oxford Cryostream 700). 
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_reflns_number            11995
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         26.124
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3607
_reflns_number_gt                2599
_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       'APEX2 ver. 2010.3 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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     
'w=1/[σ²(Fo²)+(0.0444P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3607
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
P1 P 0.61692(6) 0.64854(5) 0.27110(5) 0.01620(15) Uani 1 1 d . . . . .
F1 F 0.54471(14) 0.82879(12) -0.01135(13) 0.0342(3) Uani 1 1 d . . . . .
B1 B 0.7212(3) 0.7120(2) 0.1412(2) 0.0198(5) Uani 1 1 d . . . . .
C1 C 0.6729(2) 0.84896(18) 0.0881(2) 0.0204(5) Uani 1 1 d . . . . .
H1 H 0.847(3) 0.727(2) 0.195(2) 0.030(6) Uiso 1 1 d . . . . .
F2 F 0.63767(14) 0.94206(11) 0.18038(12) 0.0308(3) Uani 1 1 d . . . . .
C2 C 0.7960(3) 0.92405(19) 0.0340(2) 0.0233(5) Uani 1 1 d . . . . .
H2 H 0.700(2) 0.632(2) 0.059(2) 0.034(6) Uiso 1 1 d . . . . .
F3 F 0.91899(15) 0.97075(13) 0.12891(14) 0.0390(4) Uani 1 1 d . . . . .
C3 C 0.4119(2) 0.60149(18) 0.22496(19) 0.0175(4) Uani 1 1 d . . . . .
C4 C 0.3423(2) 0.47899(18) 0.2490(2) 0.0202(5) Uani 1 1 d . . . . .
H4 H 0.4022 0.4173 0.2868 0.024 Uiso 1 1 calc R U . . .
F4 F 0.74993(14) 1.03151(10) -0.02096(12) 0.0289(3) Uani 1 1 d . . . . .
F5 F 0.84362(16) 0.84503(11) -0.05505(13) 0.0369(4) Uani 1 1 d . . . . .
C5 C 0.1847(2) 0.4494(2) 0.2166(2) 0.0230(5) Uani 1 1 d . . . . .
H5 H 0.1389 0.3676 0.2327 0.028 Uiso 1 1 calc R U . . .
C6 C 0.0938(2) 0.5402(2) 0.1604(2) 0.0246(5) Uani 1 1 d . . . . .
H6 H -0.0125 0.5198 0.1394 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7007(2) 0.49796(18) 0.31203(19) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.3197(2) 0.6920(2) 0.1667(2) 0.0222(5) Uani 1 1 d . . . . .
H8 H 0.3648 0.7733 0.1489 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1619(3) 0.6612(2) 0.1356(2) 0.0268(5) Uani 1 1 d . . . . .
H7 H 0.1012 0.7223 0.0977 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7736(2) 0.48410(19) 0.4380(2) 0.0210(5) Uani 1 1 d . . . . .
H10 H 0.7786 0.5530 0.5053 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8389(2) 0.36767(19) 0.4636(2) 0.0264(5) Uani 1 1 d . . . . .
H11 H 0.8887 0.3591 0.5477 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8299(3) 0.2642(2) 0.3641(2) 0.0289(5) Uani 1 1 d . . . . .
H12 H 0.8728 0.1858 0.3816 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7571(3) 0.27750(19) 0.2383(2) 0.0283(5) Uani 1 1 d . . . . .
H13 H 0.7511 0.2078 0.1716 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6934(2) 0.39353(18) 0.2117(2) 0.0224(5) Uani 1 1 d . . . . .
H14 H 0.6456 0.4024 0.1271 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6505(2) 0.76593(18) 0.41952(19) 0.0173(4) Uani 1 1 d . . . . .
C16 C 0.5391(3) 0.7778(2) 0.4938(2) 0.0266(5) Uani 1 1 d . . . . .
H16 H 0.4446 0.7246 0.4680 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5687(3) 0.8690(2) 0.6064(2) 0.0336(6) Uani 1 1 d . . . . .
H17 H 0.4939 0.8767 0.6559 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7073(3) 0.9477(2) 0.6450(2) 0.0314(6) Uani 1 1 d . . . . .
H18 H 0.7260 1.0094 0.7200 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8199(3) 0.9358(2) 0.5729(2) 0.0357(6) Uani 1 1 d . . . . .
H19 H 0.9147 0.9882 0.6000 0.043 Uiso 1 1 calc R U . . .
C20 C 0.7904(3) 0.8452(2) 0.4598(2) 0.0320(6) Uani 1 1 d . . . . .
H20 H 0.8655 0.8378 0.4107 0.038 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
P1 C3 1.804(2) . ?
P1 C9 1.8097(18) . ?
P1 C15 1.816(2) . ?
P1 B1 1.932(2) . ?
F1 C1 1.378(2) . ?
B1 C1 1.607(3) . ?
B1 H1 1.14(2) . ?
B1 H2 1.09(2) . ?
C1 F2 1.383(2) . ?
C1 C2 1.512(3) . ?
C2 F5 1.328(2) . ?
C2 F4 1.342(2) . ?
C2 F3 1.343(2) . ?
C3 C4 1.396(3) . ?
C3 C8 1.397(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C9 C10 1.390(3) . ?
C9 C14 1.398(3) . ?
C8 C7 1.381(3) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.381(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.388(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C3 P1 C9 106.61(9) . . ?
C3 P1 C15 106.26(9) . . ?
C9 P1 C15 107.45(9) . . ?
C3 P1 B1 117.82(11) . . ?
C9 P1 B1 104.85(9) . . ?
C15 P1 B1 113.25(10) . . ?
C1 B1 P1 116.22(14) . . ?
C1 B1 H1 110.5(10) . . ?
P1 B1 H1 102.2(11) . . ?
C1 B1 H2 108.8(12) . . ?
P1 B1 H2 107.3(12) . . ?
H1 B1 H2 111.8(15) . . ?
F1 C1 F2 104.45(14) . . ?
F1 C1 C2 104.96(17) . . ?
F2 C1 C2 105.03(15) . . ?
F1 C1 B1 113.32(16) . . ?
F2 C1 B1 114.53(17) . . ?
C2 C1 B1 113.56(16) . . ?
F5 C2 F4 107.45(17) . . ?
F5 C2 F3 107.37(17) . . ?
F4 C2 F3 106.24(15) . . ?
F5 C2 C1 111.59(16) . . ?
F4 C2 C1 113.25(17) . . ?
F3 C2 C1 110.62(18) . . ?
C4 C3 C8 119.00(19) . . ?
C4 C3 P1 121.98(15) . . ?
C8 C3 P1 118.99(15) . . ?
C5 C4 C3 120.01(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.69(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C10 C9 C14 119.49(17) . . ?
C10 C9 P1 122.44(14) . . ?
C14 C9 P1 118.06(15) . . ?
C7 C8 C3 120.28(19) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C6 C7 C8 120.38(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C11 C10 C9 120.08(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.96(18) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.29(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.03(19) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C20 C15 C16 119.14(19) . . ?
C20 C15 P1 119.17(15) . . ?
C16 C15 P1 121.69(17) . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.6(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.7(2) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.059

