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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1452951'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_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 H26 B2 F2'
_chemical_formula_sum            'C20 H26 B2 F2'
_chemical_formula_weight         326.03

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'

_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                   9.024(3)
_cell_length_b                   15.783(8)
_cell_length_c                   12.907(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.65(2)
_cell_angle_gamma                90
_cell_volume                     1826.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.73

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.750
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_T_max  0.7454
_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                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            27350
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3722
_reflns_number_gt                2938
_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. V7.68A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V7.68A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_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          
;
 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)+(0.0400P)²+0.8388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
F1 F 1.09027(11) 0.32379(8) 0.43890(8) 0.0540(3) Uani 1 1 d . . . . .
C1 C 0.74578(15) 0.36962(9) 0.32321(11) 0.0235(3) Uani 1 1 d . . . . .
B1 B 1.02728(19) 0.32582(13) 0.34044(16) 0.0356(4) Uani 1 1 d . . . . .
F2 F 1.05341(11) 0.25654(7) 0.28702(10) 0.0536(3) Uani 1 1 d . . . . .
C2 C 0.65691(15) 0.31500(9) 0.25684(11) 0.0246(3) Uani 1 1 d . . . . .
B2 B 0.90292(18) 0.40087(11) 0.29284(13) 0.0255(4) Uani 1 1 d . . . . .
C3 C 0.52190(16) 0.28416(9) 0.28637(11) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.48164(15) 0.30808(10) 0.38319(12) 0.0279(3) Uani 1 1 d . . . . .
H4 H 0.3898 0.2881 0.4032 0.033 Uiso 1 1 calc R U . . .
C5 C 0.57006(16) 0.35989(10) 0.45158(11) 0.0271(3) Uani 1 1 d . . . . .
C6 C 0.70384(15) 0.39115(9) 0.42139(11) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.70582(19) 0.28788(11) 0.15350(12) 0.0353(4) Uani 1 1 d . . . . .
H7A H 0.8017 0.3144 0.1446 0.053 Uiso 1 1 calc R U . . .
H7B H 0.6308 0.3056 0.0966 0.053 Uiso 1 1 calc R U . . .
H7C H 0.7166 0.2261 0.1524 0.053 Uiso 1 1 calc R U . . .
C8 C 0.42473(17) 0.22547(11) 0.21589(13) 0.0348(4) Uani 1 1 d . . . . .
H8A H 0.4032 0.2514 0.1468 0.052 Uiso 1 1 calc R U . . .
H8B H 0.3311 0.2153 0.2455 0.052 Uiso 1 1 calc R U . . .
H8C H 0.4767 0.1715 0.2096 0.052 Uiso 1 1 calc R U . . .
C9 C 0.52355(19) 0.38119(12) 0.55781(13) 0.0375(4) Uani 1 1 d . . . . .
H9A H 0.4236 0.3585 0.5630 0.056 Uiso 1 1 calc R U . . .
H9B H 0.5224 0.4428 0.5667 0.056 Uiso 1 1 calc R U . . .
H9C H 0.5946 0.3560 0.6124 0.056 Uiso 1 1 calc R U . . .
C10 C 0.80284(18) 0.44918(11) 0.49215(12) 0.0343(4) Uani 1 1 d . . . . .
H10A H 0.7490 0.5017 0.5034 0.051 Uiso 1 1 calc R U . . .
H10B H 0.8930 0.4624 0.4597 0.051 Uiso 1 1 calc R U . . .
H10C H 0.8307 0.4211 0.5593 0.051 Uiso 1 1 calc R U . . .
C11 C 0.93572(15) 0.47811(9) 0.22444(11) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.82002(15) 0.53261(9) 0.17795(11) 0.0248(3) Uani 1 1 d . . . . .
C13 C 0.84861(16) 0.58982(9) 0.09991(11) 0.0248(3) Uani 1 1 d . . . . .
C14 C 0.99239(16) 0.59546(9) 0.07222(11) 0.0258(3) Uani 1 1 d . . . . .
H14 H 1.0103 0.6328 0.0173 0.031 Uiso 1 1 calc R U . . .
C15 C 1.11130(15) 0.54908(9) 0.12112(11) 0.0236(3) Uani 1 1 d . . . . .
C16 C 1.08369(15) 0.48988(9) 0.19681(11) 0.0226(3) Uani 1 1 d . . . . .
C17 C 0.66446(17) 0.53207(11) 0.21134(14) 0.0374(4) Uani 1 1 d . . . . .
H17A H 0.6017 0.4922 0.1677 0.056 Uiso 1 1 calc R U . . .
H17B H 0.6215 0.5890 0.2034 0.056 Uiso 1 1 calc R U . . .
H17C H 0.6696 0.5146 0.2845 0.056 Uiso 1 1 calc R U . . .
C18 C 0.72930(17) 0.64691(10) 0.04577(13) 0.0329(4) Uani 1 1 d . . . . .
H18A H 0.7039 0.6909 0.0943 0.049 Uiso 1 1 calc R U . . .
H18B H 0.6403 0.6133 0.0226 0.049 Uiso 1 1 calc R U . . .
H18C H 0.7665 0.6736 -0.0148 0.049 Uiso 1 1 calc R U . . .
C19 C 1.26596(17) 0.56581(11) 0.09134(12) 0.0322(4) Uani 1 1 d . . . . .
H19A H 1.3281 0.5910 0.1507 0.048 Uiso 1 1 calc R U . . .
H19B H 1.2593 0.6049 0.0320 0.048 Uiso 1 1 calc R U . . .
H19C H 1.3107 0.5123 0.0720 0.048 Uiso 1 1 calc R U . . .
C20 C 1.21524(16) 0.43982(10) 0.24806(12) 0.0305(4) Uani 1 1 d . . . . .
H20A H 1.2220 0.3858 0.2115 0.046 Uiso 1 1 calc R U . . .
H20B H 1.2017 0.4290 0.3211 0.046 Uiso 1 1 calc R U . . .
H20C H 1.3072 0.4723 0.2448 0.046 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 B1 1.331(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.405(2) . ?
C1 B2 1.593(2) . ?
B1 F2 1.328(2) . ?
B1 B2 1.697(3) . ?
C2 C3 1.405(2) . ?
C2 C7 1.514(2) . ?
B2 C11 1.554(2) . ?
C3 C4 1.393(2) . ?
C3 C8 1.507(2) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(2) . ?
C5 C9 1.517(2) . ?
C6 C10 1.511(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.430(2) . ?
C11 C16 1.434(2) . ?
C12 C13 1.399(2) . ?
C12 C17 1.515(2) . ?
C13 C14 1.388(2) . ?
C13 C18 1.512(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(2) . ?
C15 C19 1.513(2) . ?
C16 C20 1.513(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 C1 C6 120.36(13) . . ?
C2 C1 B2 120.21(12) . . ?
C6 C1 B2 119.17(13) . . ?
F2 B1 F1 113.20(16) . . ?
F2 B1 B2 122.44(16) . . ?
F1 B1 B2 123.62(16) . . ?
C1 C2 C3 120.03(13) . . ?
C1 C2 C7 120.54(13) . . ?
C3 C2 C7 119.42(14) . . ?
C11 B2 C1 128.06(13) . . ?
C11 B2 B1 126.29(13) . . ?
C1 B2 B1 105.37(13) . . ?
C4 C3 C2 118.27(14) . . ?
C4 C3 C8 120.94(14) . . ?
C2 C3 C8 120.77(14) . . ?
C5 C4 C3 122.71(13) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 118.80(14) . . ?
C4 C5 C9 120.46(14) . . ?
C6 C5 C9 120.73(14) . . ?
C5 C6 C1 119.76(14) . . ?
C5 C6 C10 120.92(13) . . ?
C1 C6 C10 119.31(13) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.27(13) . . ?
C12 C11 B2 122.17(13) . . ?
C16 C11 B2 119.16(12) . . ?
C13 C12 C11 120.25(13) . . ?
C13 C12 C17 117.55(13) . . ?
C11 C12 C17 122.19(13) . . ?
C14 C13 C12 118.85(13) . . ?
C14 C13 C18 118.67(13) . . ?
C12 C13 C18 122.47(13) . . ?
C13 C14 C15 123.05(13) . . ?
C13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C14 C15 C16 118.69(13) . . ?
C14 C15 C19 118.65(13) . . ?
C16 C15 C19 122.65(13) . . ?
C15 C16 C11 120.53(13) . . ?
C15 C16 C20 117.47(12) . . ?
C11 C16 C20 121.99(13) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C3 2.6(2) . . . . ?
B2 C1 C2 C3 176.77(13) . . . . ?
C6 C1 C2 C7 -176.69(14) . . . . ?
B2 C1 C2 C7 -2.5(2) . . . . ?
C2 C1 B2 C11 86.5(2) . . . . ?
C6 C1 B2 C11 -99.29(18) . . . . ?
C2 C1 B2 B1 -87.68(16) . . . . ?
C6 C1 B2 B1 86.54(17) . . . . ?
F2 B1 B2 C11 -88.0(2) . . . . ?
F1 B1 B2 C11 102.50(19) . . . . ?
F2 B1 B2 C1 86.28(17) . . . . ?
F1 B1 B2 C1 -83.19(18) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C7 C2 C3 C4 178.12(14) . . . . ?
C1 C2 C3 C8 179.90(13) . . . . ?
C7 C2 C3 C8 -0.8(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C8 C3 C4 C5 178.03(14) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C3 C4 C5 C9 -177.63(14) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C9 C5 C6 C1 179.08(14) . . . . ?
C4 C5 C6 C10 178.84(14) . . . . ?
C9 C5 C6 C10 -2.0(2) . . . . ?
C2 C1 C6 C5 -2.0(2) . . . . ?
B2 C1 C6 C5 -176.20(13) . . . . ?
C2 C1 C6 C10 179.11(14) . . . . ?
B2 C1 C6 C10 4.9(2) . . . . ?
C1 B2 C11 C12 -0.4(2) . . . . ?
B1 B2 C11 C12 172.62(15) . . . . ?
C1 B2 C11 C16 -173.06(14) . . . . ?
B1 B2 C11 C16 0.0(2) . . . . ?
C16 C11 C12 C13 6.3(2) . . . . ?
B2 C11 C12 C13 -166.39(13) . . . . ?
C16 C11 C12 C17 -172.74(14) . . . . ?
B2 C11 C12 C17 14.6(2) . . . . ?
C11 C12 C13 C14 -3.0(2) . . . . ?
C17 C12 C13 C14 176.07(14) . . . . ?
C11 C12 C13 C18 178.03(13) . . . . ?
C17 C12 C13 C18 -2.9(2) . . . . ?
C12 C13 C14 C15 -2.5(2) . . . . ?
C18 C13 C14 C15 176.50(13) . . . . ?
C13 C14 C15 C16 4.4(2) . . . . ?
C13 C14 C15 C19 -174.62(14) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
C19 C15 C16 C11 178.16(13) . . . . ?
C14 C15 C16 C20 179.50(13) . . . . ?
C19 C15 C16 C20 -1.5(2) . . . . ?
C12 C11 C16 C15 -4.4(2) . . . . ?
B2 C11 C16 C15 168.57(13) . . . . ?
C12 C11 C16 C20 175.27(13) . . . . ?
B2 C11 C16 C20 -11.8(2) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1452952'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H31 B2 F2 P'
_chemical_formula_sum            'C21 H31 B2 F2 P'
_chemical_formula_weight         374.05

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   8.463(2)
_cell_length_b                   14.8650(19)
_cell_length_c                   32.625(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4104.4(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_T_max  0.7454
_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                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_detector                 'CCD area detector (Apex1)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            66180
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.711
_diffrn_reflns_theta_max         26.371
_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             4198
_reflns_number_gt                3424
_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       'Smart NT ver. 5.63 (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, 2012)'
_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          
;
 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)+(0.0462P)²+2.7842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4198
_refine_ls_number_parameters     263
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_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 0.86546(5) 0.57081(3) 0.60525(2) 0.01900(13) Uani 1 1 d . . . . .
C1 C 0.5720(2) 0.42809(10) 0.59880(5) 0.0143(3) Uani 1 1 d . . . . .
B1 B 0.8159(3) 0.39074(15) 0.64203(7) 0.0270(5) Uani 1 1 d . . . . .
B2 B 0.7040(2) 0.48071(12) 0.62777(5) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.4399(2) 0.38887(10) 0.61875(5) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.5798(2) 0.41454(10) 0.55569(5) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.3266(2) 0.33681(11) 0.55394(5) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.3217(2) 0.34523(11) 0.59637(5) 0.0187(4) Uani 1 1 d . . . . .
H3 H 0.2344 0.3203 0.6107 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4591(2) 0.37090(11) 0.53450(5) 0.0187(4) Uani 1 1 d . . . . .
H5 H 0.4681 0.3643 0.5056 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1926(2) 0.29372(14) 0.53050(6) 0.0319(5) Uani 1 1 d . . . . .
H00V H 0.1402 0.3392 0.5135 0.048 Uiso 1 1 calc R U . . .
H00W H 0.1163 0.2681 0.5498 0.048 Uiso 1 1 calc R U . . .
H00X H 0.2344 0.2459 0.5129 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4113(2) 0.39233(12) 0.66464(5) 0.0222(4) Uani 1 1 d . . . . .
H00I H 0.3636 0.4502 0.6719 0.033 Uiso 1 1 calc R U . . .
H00J H 0.5121 0.3855 0.6791 0.033 Uiso 1 1 calc R U . . .
H00K H 0.3399 0.3435 0.6726 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7177(2) 0.44657(12) 0.53062(5) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.7020 0.4295 0.5019 0.034 Uiso 1 1 calc R U . . .
H00F H 0.8150 0.4189 0.5409 0.034 Uiso 1 1 calc R U . . .
H00G H 0.7260 0.5122 0.5327 0.034 Uiso 1 1 calc R U . . .
C10 C 0.62602(19) 0.54773(10) 0.66235(5) 0.0149(3) Uani 1 1 d . . . . .
C13 C 0.5065(2) 0.67930(12) 0.71839(5) 0.0246(4) Uani 1 1 d . . . . .
C14 C 0.4496(2) 0.67304(11) 0.67890(5) 0.0222(4) Uani 1 1 d . . . . .
H00L H 0.3692 0.7134 0.6703 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5063(2) 0.60932(11) 0.65101(5) 0.0177(4) Uani 1 1 d . . . . .
C16 C 0.7923(2) 0.48409(12) 0.72187(5) 0.0267(4) Uani 1 1 d . . . . .
H00M H 0.8856 0.4799 0.7042 0.040 Uiso 1 1 calc R U . . .
H00N H 0.7418 0.4249 0.7239 0.040 Uiso 1 1 calc R U . . .
H00O H 0.8243 0.5042 0.7492 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4532(3) 0.75380(13) 0.74673(6) 0.0367(5) Uani 1 1 d . . . . .
H011 H 0.5114 0.8090 0.7403 0.055 Uiso 1 1 calc R U . . .
H012 H 0.4739 0.7364 0.7752 0.055 Uiso 1 1 calc R U . . .
H013 H 0.3398 0.7643 0.7430 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4279(2) 0.60867(12) 0.60940(5) 0.0234(4) Uani 1 1 d . . . . .
H00A H 0.5078 0.5982 0.5882 0.035 Uiso 1 1 calc R U . . .
H00C H 0.3764 0.6668 0.6046 0.035 Uiso 1 1 calc R U . . .
H18 H 0.3488 0.5606 0.6084 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7893(2) 0.67561(12) 0.58483(6) 0.0286(4) Uani 1 1 d . . . . .
H00S H 0.7349 0.6640 0.5588 0.043 Uiso 1 1 calc R U . . .
H00T H 0.8770 0.7174 0.5802 0.043 Uiso 1 1 calc R U . . .
H00U H 0.7149 0.7020 0.6044 0.043 Uiso 1 1 calc R U . . .
C20 C 0.9830(3) 0.60969(15) 0.64827(6) 0.0364(5) Uani 1 1 d . . . . .
H00Y H 1.0465 0.5597 0.6589 0.055 Uiso 1 1 calc R U . . .
H00Z H 0.9129 0.6321 0.6699 0.055 Uiso 1 1 calc R U . . .
H010 H 1.0531 0.6583 0.6392 0.055 Uiso 1 1 calc R U . . .
C21 C 1.0237(2) 0.54275(14) 0.56935(6) 0.0277(4) Uani 1 1 d . . . . .
H00P H 0.9801 0.5376 0.5416 0.041 Uiso 1 1 calc R U . . .
H00Q H 1.0718 0.4854 0.5773 0.041 Uiso 1 1 calc R U . . .
H00R H 1.1040 0.5902 0.5699 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6176(2) 0.61614(12) 0.73056(5) 0.0240(4) Uani 1 1 d . . . . .
H00H H 0.6548 0.6173 0.7580 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6768(2) 0.55090(11) 0.70382(5) 0.0191(4) Uani 1 1 d . . . . .
F1A F 0.9435(6) 0.3643(3) 0.6198(2) 0.0462(12) Uani 0.502(11) 1 d . U P A 1
F2A F 0.771(4) 0.322(2) 0.6598(8) 0.028(2) Uani 0.502(11) 1 d . U P A 1
F1B F 0.9775(6) 0.3881(4) 0.6380(2) 0.0494(13) Uani 0.498(11) 1 d . U P A 2
F2B F 0.757(4) 0.318(2) 0.6651(8) 0.0234(18) Uani 0.498(11) 1 d . U P A 2


_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 C19 1.8126(19) . ?
P1 C20 1.815(2) . ?
P1 C21 1.8273(19) . ?
P1 B2 2.0495(19) . ?
C1 C2 1.419(2) . ?
C1 C6 1.422(2) . ?
C1 B2 1.660(2) . ?
B1 F2A 1.24(3) . ?
B1 F1A 1.359(5) . ?
B1 F1B 1.374(5) . ?
B1 F2B 1.41(3) . ?
B1 B2 1.704(3) . ?
B2 C10 1.643(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.518(2) . ?
C6 C5 1.394(2) . ?
C6 C9 1.503(2) . ?
C4 C5 1.385(2) . ?
C4 C3 1.390(2) . ?
C4 C8 1.510(2) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C8 H00V 0.9800 . ?
C8 H00W 0.9800 . ?
C8 H00X 0.9800 . ?
C7 H00I 0.9800 . ?
C7 H00J 0.9800 . ?
C7 H00K 0.9800 . ?
C9 H9 0.9800 . ?
C9 H00F 0.9800 . ?
C9 H00G 0.9800 . ?
C10 C15 1.415(2) . ?
C10 C11 1.421(2) . ?
C13 C14 1.378(3) . ?
C13 C12 1.387(3) . ?
C13 C17 1.511(2) . ?
C14 C15 1.398(2) . ?
C14 H00L 0.9500 . ?
C15 C18 1.511(2) . ?
C16 C11 1.513(3) . ?
C16 H00M 0.9800 . ?
C16 H00N 0.9800 . ?
C16 H00O 0.9800 . ?
C17 H011 0.9800 . ?
C17 H012 0.9800 . ?
C17 H013 0.9800 . ?
C18 H00A 0.9800 . ?
C18 H00C 0.9800 . ?
C18 H18 0.9800 . ?
C19 H00S 0.9800 . ?
C19 H00T 0.9800 . ?
C19 H00U 0.9800 . ?
C20 H00Y 0.9800 . ?
C20 H00Z 0.9800 . ?
C20 H010 0.9800 . ?
C21 H00P 0.9800 . ?
C21 H00Q 0.9800 . ?
C21 H00R 0.9800 . ?
C12 C11 1.397(2) . ?
C12 H00H 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
C19 P1 C20 101.85(10) . . ?
C19 P1 C21 102.78(9) . . ?
C20 P1 C21 99.60(10) . . ?
C19 P1 B2 117.15(9) . . ?
C20 P1 B2 107.24(9) . . ?
C21 P1 B2 124.69(9) . . ?
C2 C1 C6 115.60(15) . . ?
C2 C1 B2 117.57(14) . . ?
C6 C1 B2 126.77(15) . . ?
F2A B1 F1A 104.9(15) . . ?
F1B B1 F2B 112.5(14) . . ?
F2A B1 B2 127.3(15) . . ?
F1A B1 B2 121.5(3) . . ?
F1B B1 B2 123.3(3) . . ?
F2B B1 B2 123.4(14) . . ?
C10 B2 C1 113.97(14) . . ?
C10 B2 B1 120.77(14) . . ?
C1 B2 B1 99.20(13) . . ?
C10 B2 P1 96.76(10) . . ?
C1 B2 P1 123.56(11) . . ?
B1 B2 P1 103.90(12) . . ?
C3 C2 C1 120.99(15) . . ?
C3 C2 C7 114.63(15) . . ?
C1 C2 C7 124.36(15) . . ?
C5 C6 C1 121.50(16) . . ?
C5 C6 C9 116.53(15) . . ?
C1 C6 C9 121.97(15) . . ?
C5 C4 C3 116.58(16) . . ?
C5 C4 C8 122.10(16) . . ?
C3 C4 C8 121.32(17) . . ?
C4 C3 C2 122.69(16) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C4 C5 C6 122.45(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C4 C8 H00V 109.5 . . ?
C4 C8 H00W 109.5 . . ?
H00V C8 H00W 109.5 . . ?
C4 C8 H00X 109.5 . . ?
H00V C8 H00X 109.5 . . ?
H00W C8 H00X 109.5 . . ?
C2 C7 H00I 109.5 . . ?
C2 C7 H00J 109.5 . . ?
H00I C7 H00J 109.5 . . ?
C2 C7 H00K 109.5 . . ?
H00I C7 H00K 109.5 . . ?
H00J C7 H00K 109.5 . . ?
C6 C9 H9 109.5 . . ?
C6 C9 H00F 109.5 . . ?
H9 C9 H00F 109.5 . . ?
C6 C9 H00G 109.5 . . ?
H9 C9 H00G 109.5 . . ?
H00F C9 H00G 109.5 . . ?
C15 C10 C11 116.37(15) . . ?
C15 C10 B2 120.04(14) . . ?
C11 C10 B2 123.53(15) . . ?
C14 C13 C12 117.29(16) . . ?
C14 C13 C17 121.15(18) . . ?
C12 C13 C17 121.53(18) . . ?
C13 C14 C15 122.31(17) . . ?
C13 C14 H00L 118.8 . . ?
C15 C14 H00L 118.8 . . ?
C14 C15 C10 120.92(16) . . ?
C14 C15 C18 116.01(16) . . ?
C10 C15 C18 123.03(14) . . ?
C11 C16 H00M 109.5 . . ?
C11 C16 H00N 109.5 . . ?
H00M C16 H00N 109.5 . . ?
C11 C16 H00O 109.5 . . ?
H00M C16 H00O 109.5 . . ?
H00N C16 H00O 109.5 . . ?
C13 C17 H011 109.5 . . ?
C13 C17 H012 109.5 . . ?
H011 C17 H012 109.5 . . ?
C13 C17 H013 109.5 . . ?
H011 C17 H013 109.5 . . ?
H012 C17 H013 109.5 . . ?
C15 C18 H00A 109.5 . . ?
C15 C18 H00C 109.5 . . ?
H00A C18 H00C 109.5 . . ?
C15 C18 H18 109.5 . . ?
H00A C18 H18 109.5 . . ?
H00C C18 H18 109.5 . . ?
P1 C19 H00S 109.5 . . ?
P1 C19 H00T 109.5 . . ?
H00S C19 H00T 109.5 . . ?
P1 C19 H00U 109.5 . . ?
H00S C19 H00U 109.5 . . ?
H00T C19 H00U 109.5 . . ?
P1 C20 H00Y 109.5 . . ?
P1 C20 H00Z 109.5 . . ?
H00Y C20 H00Z 109.5 . . ?
P1 C20 H010 109.5 . . ?
H00Y C20 H010 109.5 . . ?
H00Z C20 H010 109.5 . . ?
P1 C21 H00P 109.5 . . ?
P1 C21 H00Q 109.5 . . ?
H00P C21 H00Q 109.5 . . ?
P1 C21 H00R 109.5 . . ?
H00P C21 H00R 109.5 . . ?
H00Q C21 H00R 109.5 . . ?
C13 C12 C11 122.28(17) . . ?
C13 C12 H00H 118.9 . . ?
C11 C12 H00H 118.9 . . ?
C12 C11 C10 120.62(16) . . ?
C12 C11 C16 116.37(16) . . ?
C10 C11 C16 122.99(15) . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1452953'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H31 B2 F2 O3 P'
_chemical_formula_sum            'C21 H31 B2 F2 O3 P'
_chemical_formula_weight         422.05

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'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.300(6)
_cell_length_b                   14.375(10)
_cell_length_c                   15.204(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.850(14)
_cell_angle_gamma                90
_cell_volume                     2176(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3518
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.509
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5618
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SadAbs 2014/4 (Bruker AXS)'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0620
-1.00 0.00 0.00 0.0320
-2.00 -2.00 -1.00 0.1300
2.00 2.00 1.00 0.1060
0.00 -2.00 -1.00 0.2100
0.00 -1.00 -2.00 0.2180
0.00 1.00 2.00 0.2270
0.00 0.00 -1.00 0.2130
0.00 0.00 1.00 0.2380
0.00 -1.00 1.00 0.2390
0.00 1.00 0.00 0.0900
0.00 -1.00 0.00 0.1660

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14236
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5394
_reflns_number_gt                4112
_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, 2012)'
_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          
;
 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.
 The for the 1,2- and 1,3-distances in XXX were restraint with RIGU keyword in ShelXL 
 input ('enhnaced rigid bond' restraint for all bonds in the connectivity list. 
 Standard values of 0.004 for both parameters s1 and s2 were used).
 The displacement parameters of atoms XXX and XXX of the residue YYY
 were restrained to the same value with similarity restraint SIMU. 
 The Uii displacement parameters of atoms XXX and YYY were restrained with 
 ISOR keyword to approximate isotropic behavior. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+1.4263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5394
_refine_ls_number_parameters     299
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.066
_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
B2 B 0.7495(2) 0.36527(14) 0.23681(17) 0.0193(5) Uani 1 1 d . . . . .
B1_1 B 0.8726(3) 0.4191(2) 0.1984(3) 0.0264(8) Uani 0.731(4) 1 d D U P A 1
F1_1 F 1.00311(18) 0.39860(13) 0.22934(17) 0.0426(7) Uani 0.731(4) 1 d D U P A
1
F2_1 F 0.8579(3) 0.49699(19) 0.1488(2) 0.0340(8) Uani 0.731(4) 1 d D U P A 1
B1_11 B 0.8636(9) 0.4115(5) 0.1809(8) 0.0292(18) Uani 0.269(4) 1 d D U P A 2
F1_11 F 0.9450(5) 0.3630(3) 0.1422(4) 0.0432(16) Uani 0.269(4) 1 d D U P A 2
F2_11 F 0.8892(10) 0.5024(4) 0.1768(7) 0.0348(17) Uani 0.269(4) 1 d D U P A 2
P1_2 P 0.80764(5) 0.23511(3) 0.24526(4) 0.01947(14) Uani 1 1 d . . . . .
O2_2 O 0.74463(15) 0.17091(9) 0.30772(12) 0.0266(4) Uani 1 1 d . . . . .
O3_2 O 0.96324(14) 0.21620(10) 0.27587(11) 0.0254(3) Uani 1 1 d . . . . .
O4_2 O 0.76974(14) 0.18914(10) 0.14727(11) 0.0244(3) Uani 1 1 d . . . . .
C5_2 C 0.7907(3) 0.07570(14) 0.3271(2) 0.0379(6) Uani 1 1 d . . . . .
H5A_2 H 0.7286 0.0425 0.3531 0.057 Uiso 1 1 calc R U . . .
H5B_2 H 0.8778 0.0759 0.3694 0.057 Uiso 1 1 calc R U . . .
H5C_2 H 0.7962 0.0458 0.2717 0.057 Uiso 1 1 calc R U . . .
C6_2 C 1.0468(2) 0.17937(18) 0.22131(18) 0.0333(5) Uani 1 1 d . . . . .
H6A_2 H 1.1385 0.1778 0.2567 0.050 Uiso 1 1 calc R U . . .
H6B_2 H 1.0397 0.2183 0.1690 0.050 Uiso 1 1 calc R U . . .
H6C_2 H 1.0180 0.1175 0.2019 0.050 Uiso 1 1 calc R U . . .
C7_2 C 0.6408(2) 0.14588(15) 0.10677(19) 0.0321(5) Uani 1 1 d . . . . .
H7A_2 H 0.6539 0.0812 0.0959 0.048 Uiso 1 1 calc R U . . .
H7B_2 H 0.5995 0.1761 0.0502 0.048 Uiso 1 1 calc R U . . .
H7C_2 H 0.5837 0.1518 0.1475 0.048 Uiso 1 1 calc R U . . .
C1_3 C 0.59266(19) 0.35513(12) 0.17679(14) 0.0186(4) Uani 1 1 d . . . . .
C2_3 C 0.5515(2) 0.36462(13) 0.08144(15) 0.0227(4) Uani 1 1 d . . . . .
C3_3 C 0.4157(2) 0.36452(13) 0.03548(16) 0.0261(5) Uani 1 1 d . . . . .
H3_3 H 0.3916 0.3712 -0.0275 0.031 Uiso 1 1 calc R U . . .
C4_3 C 0.3147(2) 0.35477(13) 0.08093(17) 0.0250(5) Uani 1 1 d . . . . .
C5_3 C 0.3548(2) 0.34074(12) 0.17363(16) 0.0227(4) Uani 1 1 d . . . . .
H5_3 H 0.2893 0.3316 0.2050 0.027 Uiso 1 1 calc R U . . .
C6_3 C 0.4895(2) 0.33967(12) 0.22248(15) 0.0194(4) Uani 1 1 d . . . . .
C7_3 C 0.6495(2) 0.37618(16) 0.02263(17) 0.0308(5) Uani 1 1 d . . . . .
H7A_3 H 0.6043 0.3634 -0.0397 0.046 Uiso 1 1 calc R U . . .
H7B_3 H 0.7230 0.3336 0.0426 0.046 Uiso 1 1 calc R U . . .
H7C_3 H 0.6830 0.4388 0.0278 0.046 Uiso 1 1 calc R U . . .
C8_3 C 0.1683(2) 0.35836(16) 0.0301(2) 0.0377(6) Uani 1 1 d . . . . .
H8A_3 H 0.1298 0.4157 0.0437 0.057 Uiso 1 1 calc R U . . .
H8B_3 H 0.1217 0.3070 0.0485 0.057 Uiso 1 1 calc R U . . .
H8C_3 H 0.1602 0.3546 -0.0341 0.057 Uiso 1 1 calc R U . . .
C9_3 C 0.5172(2) 0.32476(13) 0.32378(15) 0.0216(4) Uani 1 1 d . . . . .
H9A_3 H 0.4419 0.2940 0.3373 0.032 Uiso 1 1 calc R U . . .
H9B_3 H 0.5312 0.3838 0.3543 0.032 Uiso 1 1 calc R U . . .
H9C_3 H 0.5961 0.2870 0.3442 0.032 Uiso 1 1 calc R U . . .
C1_4 C 0.76475(18) 0.43297(12) 0.32712(15) 0.0183(4) Uani 1 1 d . . . . .
C2_4 C 0.69723(19) 0.52094(13) 0.31320(15) 0.0210(4) Uani 1 1 d . . . . .
C3_4 C 0.6978(2) 0.57902(13) 0.38716(16) 0.0236(5) Uani 1 1 d . . . . .
H3_4 H 0.6534 0.6359 0.3760 0.028 Uiso 1 1 calc R U . . .
C4_4 C 0.7611(2) 0.55585(13) 0.47598(17) 0.0253(5) Uani 1 1 d . . . . .
C5_4 C 0.8329(2) 0.47304(14) 0.48903(16) 0.0243(4) Uani 1 1 d . . . . .
H5_4 H 0.8804 0.4569 0.5477 0.029 Uiso 1 1 calc R U . . .
C6_4 C 0.8364(2) 0.41291(13) 0.41743(16) 0.0221(4) Uani 1 1 d . . . . .
C7_4 C 0.6168(2) 0.55603(14) 0.22164(17) 0.0282(5) Uani 1 1 d . . . . .
H7A_4 H 0.6098 0.6226 0.2234 0.042 Uiso 1 1 calc R U . . .
H7B_4 H 0.5285 0.5292 0.2077 0.042 Uiso 1 1 calc R U . . .
H7C_4 H 0.6609 0.5386 0.1757 0.042 Uiso 1 1 calc R U . . .
C8_4 C 0.7481(3) 0.61493(16) 0.55510(19) 0.0360(6) Uani 1 1 d . . . . .
H8A_4 H 0.8270 0.6077 0.6045 0.054 Uiso 1 1 calc R U . . .
H8B_4 H 0.6706 0.5957 0.5744 0.054 Uiso 1 1 calc R U . . .
H8C_4 H 0.7386 0.6790 0.5368 0.054 Uiso 1 1 calc R U . . .
C9_4 C 0.9165(2) 0.32533(15) 0.44438(17) 0.0292(5) Uani 1 1 d . . . . .
H9A_4 H 0.9766 0.3332 0.5036 0.044 Uiso 1 1 calc R U . . .
H9B_4 H 0.9675 0.3124 0.4010 0.044 Uiso 1 1 calc R U . . .
H9C_4 H 0.8567 0.2744 0.4457 0.044 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
B2 C1_3 1.646(3) . ?
B2 C1_4 1.657(3) . ?
B2 B1_1 1.711(4) . ?
B2 B1_11 1.749(7) . ?
B2 P1_2 1.959(2) . ?
B1_1 F2_1 1.336(2) . ?
B1_1 F1_1 1.338(2) . ?
B1_11 F2_11 1.337(3) . ?
B1_11 F1_11 1.338(2) . ?
P1_2 O3_2 1.5737(18) . ?
P1_2 O2_2 1.5782(15) . ?
P1_2 O4_2 1.5844(18) . ?
O2_2 C5_2 1.454(2) . ?
O3_2 C6_2 1.441(2) . ?
O4_2 C7_2 1.453(3) . ?
C5_2 H5A_2 0.9600 . ?
C5_2 H5B_2 0.9600 . ?
C5_2 H5C_2 0.9600 . ?
C6_2 H6A_2 0.9600 . ?
C6_2 H6B_2 0.9600 . ?
C6_2 H6C_2 0.9600 . ?
C7_2 H7A_2 0.9600 . ?
C7_2 H7B_2 0.9600 . ?
C7_2 H7C_2 0.9600 . ?
C1_3 C2_3 1.409(3) . ?
C1_3 C6_3 1.428(3) . ?
C2_3 C3_3 1.395(3) . ?
C2_3 C7_3 1.519(3) . ?
C3_3 C4_3 1.395(3) . ?
C3_3 H3_3 0.9300 . ?
C4_3 C5_3 1.378(3) . ?
C4_3 C8_3 1.509(3) . ?
C5_3 C6_3 1.396(3) . ?
C5_3 H5_3 0.9300 . ?
C6_3 C9_3 1.508(3) . ?
C7_3 H7A_3 0.9600 . ?
C7_3 H7B_3 0.9600 . ?
C7_3 H7C_3 0.9600 . ?
C8_3 H8A_3 0.9600 . ?
C8_3 H8B_3 0.9600 . ?
C8_3 H8C_3 0.9600 . ?
C9_3 H9A_3 0.9600 . ?
C9_3 H9B_3 0.9600 . ?
C9_3 H9C_3 0.9600 . ?
C1_4 C6_4 1.412(3) . ?
C1_4 C2_4 1.433(3) . ?
C2_4 C3_4 1.399(3) . ?
C2_4 C7_4 1.513(3) . ?
C3_4 C4_4 1.382(3) . ?
C3_4 H3_4 0.9300 . ?
C4_4 C5_4 1.388(3) . ?
C4_4 C8_4 1.506(3) . ?
C5_4 C6_4 1.398(3) . ?
C5_4 H5_4 0.9300 . ?
C6_4 C9_4 1.503(3) . ?
C7_4 H7A_4 0.9600 . ?
C7_4 H7B_4 0.9600 . ?
C7_4 H7C_4 0.9600 . ?
C8_4 H8A_4 0.9600 . ?
C8_4 H8B_4 0.9600 . ?
C8_4 H8C_4 0.9600 . ?
C9_4 H9A_4 0.9600 . ?
C9_4 H9B_4 0.9600 . ?
C9_4 H9C_4 0.9600 . ?

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_3 B2 C1_4 112.49(15) . . ?
C1_3 B2 B1_1 123.97(19) . . ?
C1_4 B2 B1_1 95.5(2) . . ?
C1_3 B2 B1_11 116.8(4) . . ?
C1_4 B2 B1_11 104.3(3) . . ?
C1_3 B2 P1_2 101.06(12) . . ?
C1_4 B2 P1_2 122.97(15) . . ?
B1_1 B2 P1_2 102.33(15) . . ?
B1_11 B2 P1_2 99.4(2) . . ?
F2_1 B1_1 F1_1 110.0(2) . . ?
F2_1 B1_1 B2 125.8(2) . . ?
F1_1 B1_1 B2 123.1(2) . . ?
F2_11 B1_11 F1_11 109.7(3) . . ?
F2_11 B1_11 B2 124.0(5) . . ?
F1_11 B1_11 B2 126.2(5) . . ?
O3_2 P1_2 O2_2 105.41(9) . . ?
O3_2 P1_2 O4_2 101.12(8) . . ?
O2_2 P1_2 O4_2 106.37(9) . . ?
O3_2 P1_2 B2 117.09(9) . . ?
O2_2 P1_2 B2 115.60(9) . . ?
O4_2 P1_2 B2 109.83(10) . . ?
C5_2 O2_2 P1_2 120.61(13) . . ?
C6_2 O3_2 P1_2 127.36(15) . . ?
C7_2 O4_2 P1_2 123.72(14) . . ?
O2_2 C5_2 H5A_2 109.5 . . ?
O2_2 C5_2 H5B_2 109.5 . . ?
H5A_2 C5_2 H5B_2 109.5 . . ?
O2_2 C5_2 H5C_2 109.5 . . ?
H5A_2 C5_2 H5C_2 109.5 . . ?
H5B_2 C5_2 H5C_2 109.5 . . ?
O3_2 C6_2 H6A_2 109.5 . . ?
O3_2 C6_2 H6B_2 109.5 . . ?
H6A_2 C6_2 H6B_2 109.5 . . ?
O3_2 C6_2 H6C_2 109.5 . . ?
H6A_2 C6_2 H6C_2 109.5 . . ?
H6B_2 C6_2 H6C_2 109.5 . . ?
O4_2 C7_2 H7A_2 109.5 . . ?
O4_2 C7_2 H7B_2 109.5 . . ?
H7A_2 C7_2 H7B_2 109.5 . . ?
O4_2 C7_2 H7C_2 109.5 . . ?
H7A_2 C7_2 H7C_2 109.5 . . ?
H7B_2 C7_2 H7C_2 109.5 . . ?
C2_3 C1_3 C6_3 116.79(19) . . ?
C2_3 C1_3 B2 123.75(17) . . ?
C6_3 C1_3 B2 119.40(19) . . ?
C3_3 C2_3 C1_3 120.93(19) . . ?
C3_3 C2_3 C7_3 115.9(2) . . ?
C1_3 C2_3 C7_3 123.1(2) . . ?
C2_3 C3_3 C4_3 122.1(2) . . ?
C2_3 C3_3 H3_3 119.0 . . ?
C4_3 C3_3 H3_3 119.0 . . ?
C5_3 C4_3 C3_3 117.1(2) . . ?
C5_3 C4_3 C8_3 121.8(2) . . ?
C3_3 C4_3 C8_3 121.1(2) . . ?
C4_3 C5_3 C6_3 122.81(19) . . ?
C4_3 C5_3 H5_3 118.6 . . ?
C6_3 C5_3 H5_3 118.6 . . ?
C5_3 C6_3 C1_3 120.1(2) . . ?
C5_3 C6_3 C9_3 116.54(17) . . ?
C1_3 C6_3 C9_3 123.34(18) . . ?
C2_3 C7_3 H7A_3 109.5 . . ?
C2_3 C7_3 H7B_3 109.5 . . ?
H7A_3 C7_3 H7B_3 109.5 . . ?
C2_3 C7_3 H7C_3 109.5 . . ?
H7A_3 C7_3 H7C_3 109.5 . . ?
H7B_3 C7_3 H7C_3 109.5 . . ?
C4_3 C8_3 H8A_3 109.5 . . ?
C4_3 C8_3 H8B_3 109.5 . . ?
H8A_3 C8_3 H8B_3 109.5 . . ?
C4_3 C8_3 H8C_3 109.5 . . ?
H8A_3 C8_3 H8C_3 109.5 . . ?
H8B_3 C8_3 H8C_3 109.5 . . ?
C6_3 C9_3 H9A_3 109.5 . . ?
C6_3 C9_3 H9B_3 109.5 . . ?
H9A_3 C9_3 H9B_3 109.5 . . ?
C6_3 C9_3 H9C_3 109.5 . . ?
H9A_3 C9_3 H9C_3 109.5 . . ?
H9B_3 C9_3 H9C_3 109.5 . . ?
C6_4 C1_4 C2_4 115.90(18) . . ?
C6_4 C1_4 B2 126.92(17) . . ?
C2_4 C1_4 B2 117.17(18) . . ?
C3_4 C2_4 C1_4 120.4(2) . . ?
C3_4 C2_4 C7_4 115.40(18) . . ?
C1_4 C2_4 C7_4 124.13(19) . . ?
C4_4 C3_4 C2_4 123.04(18) . . ?
C4_4 C3_4 H3_4 118.5 . . ?
C2_4 C3_4 H3_4 118.5 . . ?
C3_4 C4_4 C5_4 116.6(2) . . ?
C3_4 C4_4 C8_4 121.9(2) . . ?
C5_4 C4_4 C8_4 121.5(2) . . ?
C4_4 C5_4 C6_4 122.6(2) . . ?
C4_4 C5_4 H5_4 118.7 . . ?
C6_4 C5_4 H5_4 118.7 . . ?
C5_4 C6_4 C1_4 121.30(18) . . ?
C5_4 C6_4 C9_4 115.3(2) . . ?
C1_4 C6_4 C9_4 123.34(19) . . ?
C2_4 C7_4 H7A_4 109.5 . . ?
C2_4 C7_4 H7B_4 109.5 . . ?
H7A_4 C7_4 H7B_4 109.5 . . ?
C2_4 C7_4 H7C_4 109.5 . . ?
H7A_4 C7_4 H7C_4 109.5 . . ?
H7B_4 C7_4 H7C_4 109.5 . . ?
C4_4 C8_4 H8A_4 109.5 . . ?
C4_4 C8_4 H8B_4 109.5 . . ?
H8A_4 C8_4 H8B_4 109.5 . . ?
C4_4 C8_4 H8C_4 109.5 . . ?
H8A_4 C8_4 H8C_4 109.5 . . ?
H8B_4 C8_4 H8C_4 109.5 . . ?
C6_4 C9_4 H9A_4 109.5 . . ?
C6_4 C9_4 H9B_4 109.5 . . ?
H9A_4 C9_4 H9B_4 109.5 . . ?
C6_4 C9_4 H9C_4 109.5 . . ?
H9A_4 C9_4 H9C_4 109.5 . . ?
H9B_4 C9_4 H9C_4 109.5 . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.064

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1452954'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16.50 H22 B Cl F N2'
_chemical_formula_sum            'C16.50 H22 B Cl F N2'
_chemical_formula_weight         313.62

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

_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                   11.043(2)
_cell_length_b                   11.083(4)
_cell_length_c                   14.473(3)
_cell_angle_alpha                92.267(9)
_cell_angle_beta                 92.359(10)
_cell_angle_gamma                113.535(10)
_cell_volume                     1619.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.50


_exptl_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 (Bruker 
Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.16
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_max          0.48
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7128
_exptl_absorpt_correction_T_max  0.7456
_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                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            30293
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7433
_reflns_number_gt                6734
_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          
;

 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. 

The crystal was a pseudo-merohedral twin with domains with second domaine
described by [0 -1 0][-1 0 0][0 0 -1] matrix. The BASF parameter was refined 
to 18%.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1193P)²+1.0508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         7433
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1_1 B 0.3302(2) 0.5085(2) 0.74677(17) 0.0105(4) Uani 1 1 d . . . . .
F1_1 F 0.26781(13) 0.48081(14) 0.65423(9) 0.0138(3) Uani 1 1 d . . . . .
B2_1 B 0.4799(2) 0.6549(2) 0.74868(17) 0.0108(5) Uani 1 1 d . . . . .
F2_1 F 0.50988(13) 0.71986(13) 0.83955(9) 0.0131(3) Uani 1 1 d . . . . .
C1_2 C 0.3126(2) 0.3701(2) 0.79467(15) 0.0116(4) Uani 1 1 d . . . . .
C2_2 C 0.1969(2) 0.2533(2) 0.77417(16) 0.0137(4) Uani 1 1 d . . . . .
C3_2 C 0.1774(3) 0.1379(2) 0.81846(17) 0.0171(5) Uani 1 1 d . . . . .
H3_2 H 0.1004 0.0607 0.8011 0.021 Uiso 1 1 calc R U . . .
C4_2 C 0.2663(3) 0.1317(2) 0.88713(18) 0.0196(5) Uani 1 1 d . . . . .
C5_2 C 0.3794(3) 0.2454(2) 0.90828(17) 0.0186(5) Uani 1 1 d . . . . .
H5_2 H 0.4409 0.2452 0.9560 0.022 Uiso 1 1 calc R U . . .
C6_2 C 0.4058(2) 0.3605(2) 0.86161(16) 0.0142(4) Uani 1 1 d . . . . .
C7_2 C 0.0865(2) 0.2456(3) 0.70502(19) 0.0201(5) Uani 1 1 d . . . . .
H7A_2 H 0.0532 0.3123 0.7233 0.030 Uiso 1 1 calc R U . . .
H7B_2 H 0.0144 0.1577 0.7040 0.030 Uiso 1 1 calc R U . . .
H7C_2 H 0.1205 0.2617 0.6432 0.030 Uiso 1 1 calc R U . . .
C8_2 C 0.2405(4) 0.0077(3) 0.9365(2) 0.0321(7) Uani 1 1 d . . . . .
H8A_2 H 0.3217 0.0154 0.9711 0.048 Uiso 1 1 calc R U . . .
H8B_2 H 0.2123 -0.0677 0.8911 0.048 Uiso 1 1 calc R U . . .
H8C_2 H 0.1707 -0.0053 0.9795 0.048 Uiso 1 1 calc R U . . .
C9_2 C 0.5395(2) 0.4721(2) 0.88502(17) 0.0172(5) Uani 1 1 d . . . . .
H9A_2 H 0.5961 0.4394 0.9210 0.026 Uiso 1 1 calc R U . . .
H9B_2 H 0.5281 0.5427 0.9216 0.026 Uiso 1 1 calc R U . . .
H9C_2 H 0.5810 0.5064 0.8277 0.026 Uiso 1 1 calc R U . . .
C1_3 C 0.6178(2) 0.6670(2) 0.70076(15) 0.0110(4) Uani 1 1 d . . . . .
C2_3 C 0.6281(2) 0.5688(2) 0.63978(15) 0.0131(4) Uani 1 1 d . . . . .
C3_3 C 0.7451(2) 0.5890(3) 0.59624(16) 0.0169(5) Uani 1 1 d . . . . .
H3_3 H 0.7471 0.5212 0.5549 0.020 Uiso 1 1 calc R U . . .
C4_3 C 0.8577(2) 0.7041(3) 0.61145(16) 0.0171(5) Uani 1 1 d . . . . .
C5_3 C 0.8505(2) 0.8005(2) 0.67261(17) 0.0169(5) Uani 1 1 d . . . . .
H5_3 H 0.9269 0.8801 0.6852 0.020 Uiso 1 1 calc R U . . .
C6_3 C 0.7347(2) 0.7845(2) 0.71628(15) 0.0130(4) Uani 1 1 d . . . . .
C7_3 C 0.5149(2) 0.4362(2) 0.61838(17) 0.0168(5) Uani 1 1 d . . . . .
H7A_3 H 0.4467 0.4468 0.5782 0.025 Uiso 1 1 calc R U . . .
H7B_3 H 0.4771 0.3995 0.6762 0.025 Uiso 1 1 calc R U . . .
H7C_3 H 0.5476 0.3763 0.5869 0.025 Uiso 1 1 calc R U . . .
C8_3 C 0.9829(3) 0.7250(3) 0.56365(19) 0.0245(6) Uani 1 1 d . . . . .
H8A_3 H 1.0008 0.7962 0.5213 0.037 Uiso 1 1 calc R U . . .
H8B_3 H 0.9721 0.6436 0.5285 0.037 Uiso 1 1 calc R U . . .
H8C_3 H 1.0571 0.7487 0.6101 0.037 Uiso 1 1 calc R U . . .
C9_3 C 0.7417(2) 0.8987(2) 0.78035(18) 0.0174(5) Uani 1 1 d . . . . .
H9A_3 H 0.7334 0.8718 0.8443 0.026 Uiso 1 1 calc R U . . .
H9B_3 H 0.6694 0.9248 0.7626 0.026 Uiso 1 1 calc R U . . .
H9C_3 H 0.8267 0.9734 0.7757 0.026 Uiso 1 1 calc R U . . .
N1_4 N 0.23067(19) 0.55721(19) 0.80475(13) 0.0112(4) Uani 1 1 d . . . . .
C2_4 C 0.1340(2) 0.5849(2) 0.76378(16) 0.0139(4) Uani 1 1 d . . . . .
H2_4 H 0.1211 0.5733 0.6982 0.017 Uiso 1 1 calc R U . . .
C3_4 C 0.0521(2) 0.6292(2) 0.81158(17) 0.0161(5) Uani 1 1 d . . . . .
H3_4 H -0.0150 0.6469 0.7791 0.019 Uiso 1 1 calc R U . . .
C4_4 C 0.0692(2) 0.6478(2) 0.90960(17) 0.0146(4) Uani 1 1 d . . . . .
C5_4 C 0.1743(2) 0.6223(2) 0.95118(16) 0.0145(4) Uani 1 1 d . . . . .
H5_4 H 0.1926 0.6361 1.0164 0.017 Uiso 1 1 calc R U . . .
C6_4 C 0.2495(2) 0.5779(2) 0.89848(15) 0.0133(4) Uani 1 1 d . . . . .
H6_4 H 0.3183 0.5606 0.9287 0.016 Uiso 1 1 calc R U . . .
N7_4 N -0.0103(2) 0.6870(2) 0.95991(16) 0.0199(4) Uani 1 1 d . . . . .
C8_4 C -0.1146(3) 0.7166(3) 0.9153(2) 0.0286(6) Uani 1 1 d . . . . .
H8A_4 H -0.0755 0.8013 0.8866 0.043 Uiso 1 1 calc R U . . .
H8B_4 H -0.1750 0.7217 0.9615 0.043 Uiso 1 1 calc R U . . .
H8C_4 H -0.1637 0.6470 0.8675 0.043 Uiso 1 1 calc R U . . .
C9_4 C 0.0179(3) 0.7175(3) 1.05921(19) 0.0243(6) Uani 1 1 d . . . . .
H9A_4 H 0.0240 0.6418 1.0886 0.036 Uiso 1 1 calc R U . . .
H9B_4 H -0.0533 0.7369 1.0853 0.036 Uiso 1 1 calc R U . . .
H9C_4 H 0.1020 0.7945 1.0706 0.036 Uiso 1 1 calc R U . . .
N1_5 N 0.43163(18) 0.75338(19) 0.68876(13) 0.0107(4) Uani 1 1 d . . . . .
C2_5 C 0.4187(2) 0.7394(2) 0.59520(16) 0.0138(4) Uani 1 1 d . . . . .
H2_5 H 0.4430 0.6754 0.5651 0.017 Uiso 1 1 calc R U . . .
C3_5 C 0.3723(2) 0.8125(2) 0.54156(16) 0.0152(4) Uani 1 1 d . . . . .
H3_5 H 0.3643 0.7977 0.4761 0.018 Uiso 1 1 calc R U . . .
C4_5 C 0.3361(2) 0.9102(2) 0.58311(16) 0.0134(4) Uani 1 1 d . . . . .
C5_5 C 0.3469(2) 0.9210(2) 0.68113(16) 0.0150(4) Uani 1 1 d . . . . .
H5_5 H 0.3216 0.9826 0.7135 0.018 Uiso 1 1 calc R U . . .
C6_5 C 0.3937(2) 0.8432(2) 0.72957(16) 0.0137(4) Uani 1 1 d . . . . .
H6_5 H 0.3997 0.8529 0.7953 0.016 Uiso 1 1 calc R U . . .
N7_5 N 0.2941(2) 0.9868(2) 0.53177(15) 0.0183(4) Uani 1 1 d . . . . .
C8_5 C 0.2744(3) 0.9638(3) 0.43123(18) 0.0228(5) Uani 1 1 d . . . . .
H8A_5 H 0.3602 0.9862 0.4044 0.034 Uiso 1 1 calc R U . . .
H8B_5 H 0.2318 1.0192 0.4063 0.034 Uiso 1 1 calc R U . . .
H8C_5 H 0.2179 0.8708 0.4154 0.034 Uiso 1 1 calc R U . . .
C9_5 C 0.2580(3) 1.0872(3) 0.5754(2) 0.0251(6) Uani 1 1 d . . . . .
H9A_5 H 0.1755 1.0447 0.6063 0.038 Uiso 1 1 calc R U . . .
H9B_5 H 0.2457 1.1429 0.5281 0.038 Uiso 1 1 calc R U . . .
H9C_5 H 0.3286 1.1417 0.6211 0.038 Uiso 1 1 calc R U . . .
C1_6 C 0.6125(4) 0.2113(3) 0.7681(2) 0.0379(7) Uani 1 1 d . . . . .
H1A_6 H 0.5848 0.1473 0.7136 0.046 Uiso 1 1 calc R U . . .
H1B_6 H 0.5466 0.2506 0.7728 0.046 Uiso 1 1 calc R U . . .
Cl2_6 Cl 0.61351(8) 0.12599(8) 0.86993(6) 0.0384(2) Uani 1 1 d . . . . .
Cl3_6 Cl 0.76512(9) 0.33428(10) 0.75110(7) 0.0485(2) 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_1 F1_1 1.444(3) . ?
B1_1 N1_4 1.649(3) . ?
B1_1 C1_2 1.652(3) . ?
B1_1 B2_1 1.794(4) . ?
B2_1 F2_1 1.434(3) . ?
B2_1 N1_5 1.652(3) . ?
B2_1 C1_3 1.657(3) . ?
C1_2 C2_2 1.419(3) . ?
C1_2 C6_2 1.422(3) . ?
C2_2 C3_2 1.396(3) . ?
C2_2 C7_2 1.518(3) . ?
C3_2 C4_2 1.391(4) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.387(4) . ?
C4_2 C8_2 1.504(4) . ?
C5_2 C6_2 1.398(3) . ?
C5_2 H5_2 0.9500 . ?
C6_2 C9_2 1.515(3) . ?
C7_2 H7A_2 0.9800 . ?
C7_2 H7B_2 0.9800 . ?
C7_2 H7C_2 0.9800 . ?
C8_2 H8A_2 0.9800 . ?
C8_2 H8B_2 0.9800 . ?
C8_2 H8C_2 0.9800 . ?
C9_2 H9A_2 0.9800 . ?
C9_2 H9B_2 0.9800 . ?
C9_2 H9C_2 0.9800 . ?
C1_3 C2_3 1.417(3) . ?
C1_3 C6_3 1.423(3) . ?
C2_3 C3_3 1.402(3) . ?
C2_3 C7_3 1.511(3) . ?
C3_3 C4_3 1.383(4) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.389(4) . ?
C4_3 C8_3 1.510(3) . ?
C5_3 C6_3 1.400(3) . ?
C5_3 H5_3 0.9500 . ?
C6_3 C9_3 1.514(3) . ?
C7_3 H7A_3 0.9800 . ?
C7_3 H7B_3 0.9800 . ?
C7_3 H7C_3 0.9800 . ?
C8_3 H8A_3 0.9800 . ?
C8_3 H8B_3 0.9800 . ?
C8_3 H8C_3 0.9800 . ?
C9_3 H9A_3 0.9800 . ?
C9_3 H9B_3 0.9800 . ?
C9_3 H9C_3 0.9800 . ?
N1_4 C2_4 1.345(3) . ?
N1_4 C6_4 1.360(3) . ?
C2_4 C3_4 1.385(3) . ?
C2_4 H2_4 0.9500 . ?
C3_4 C4_4 1.419(3) . ?
C3_4 H3_4 0.9500 . ?
C4_4 N7_4 1.350(3) . ?
C4_4 C5_4 1.417(3) . ?
C5_4 C6_4 1.364(3) . ?
C5_4 H5_4 0.9500 . ?
C6_4 H6_4 0.9500 . ?
N7_4 C8_4 1.453(3) . ?
N7_4 C9_4 1.455(4) . ?
C8_4 H8A_4 0.9800 . ?
C8_4 H8B_4 0.9800 . ?
C8_4 H8C_4 0.9800 . ?
C9_4 H9A_4 0.9800 . ?
C9_4 H9B_4 0.9800 . ?
C9_4 H9C_4 0.9800 . ?
N1_5 C6_5 1.349(3) . ?
N1_5 C2_5 1.352(3) . ?
C2_5 C3_5 1.368(3) . ?
C2_5 H2_5 0.9500 . ?
C3_5 C4_5 1.417(3) . ?
C3_5 H3_5 0.9500 . ?
C4_5 N7_5 1.350(3) . ?
C4_5 C5_5 1.415(3) . ?
C5_5 C6_5 1.370(3) . ?
C5_5 H5_5 0.9500 . ?
C6_5 H6_5 0.9500 . ?
N7_5 C9_5 1.455(3) . ?
N7_5 C8_5 1.459(3) . ?
C8_5 H8A_5 0.9800 . ?
C8_5 H8B_5 0.9800 . ?
C8_5 H8C_5 0.9800 . ?
C9_5 H9A_5 0.9800 . ?
C9_5 H9B_5 0.9800 . ?
C9_5 H9C_5 0.9800 . ?
C1_6 Cl3_6 1.728(4) . ?
C1_6 Cl2_6 1.784(4) . ?
C1_6 H1A_6 0.9900 . ?
C1_6 H1B_6 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1_1 B1_1 N1_4 102.50(17) . . ?
F1_1 B1_1 C1_2 110.45(18) . . ?
N1_4 B1_1 C1_2 102.53(16) . . ?
F1_1 B1_1 B2_1 109.08(17) . . ?
N1_4 B1_1 B2_1 103.15(17) . . ?
C1_2 B1_1 B2_1 126.02(18) . . ?
F2_1 B2_1 N1_5 102.52(17) . . ?
F2_1 B2_1 C1_3 110.38(18) . . ?
N1_5 B2_1 C1_3 103.19(16) . . ?
F2_1 B2_1 B1_1 110.16(17) . . ?
N1_5 B2_1 B1_1 101.77(17) . . ?
C1_3 B2_1 B1_1 125.59(19) . . ?
C2_2 C1_2 C6_2 115.7(2) . . ?
C2_2 C1_2 B1_1 120.7(2) . . ?
C6_2 C1_2 B1_1 123.5(2) . . ?
C3_2 C2_2 C1_2 121.1(2) . . ?
C3_2 C2_2 C7_2 115.9(2) . . ?
C1_2 C2_2 C7_2 123.0(2) . . ?
C4_2 C3_2 C2_2 122.5(2) . . ?
C4_2 C3_2 H3_2 118.7 . . ?
C2_2 C3_2 H3_2 118.7 . . ?
C5_2 C4_2 C3_2 116.9(2) . . ?
C5_2 C4_2 C8_2 121.6(3) . . ?
C3_2 C4_2 C8_2 121.6(3) . . ?
C4_2 C5_2 C6_2 122.1(2) . . ?
C4_2 C5_2 H5_2 118.9 . . ?
C6_2 C5_2 H5_2 118.9 . . ?
C5_2 C6_2 C1_2 121.4(2) . . ?
C5_2 C6_2 C9_2 116.2(2) . . ?
C1_2 C6_2 C9_2 122.3(2) . . ?
C2_2 C7_2 H7A_2 109.5 . . ?
C2_2 C7_2 H7B_2 109.5 . . ?
H7A_2 C7_2 H7B_2 109.5 . . ?
C2_2 C7_2 H7C_2 109.5 . . ?
H7A_2 C7_2 H7C_2 109.5 . . ?
H7B_2 C7_2 H7C_2 109.5 . . ?
C4_2 C8_2 H8A_2 109.5 . . ?
C4_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
C4_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C6_2 C9_2 H9A_2 109.5 . . ?
C6_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9B_2 109.5 . . ?
C6_2 C9_2 H9C_2 109.5 . . ?
H9A_2 C9_2 H9C_2 109.5 . . ?
H9B_2 C9_2 H9C_2 109.5 . . ?
C2_3 C1_3 C6_3 115.4(2) . . ?
C2_3 C1_3 B2_1 124.4(2) . . ?
C6_3 C1_3 B2_1 120.09(19) . . ?
C3_3 C2_3 C1_3 121.6(2) . . ?
C3_3 C2_3 C7_3 116.0(2) . . ?
C1_3 C2_3 C7_3 122.4(2) . . ?
C4_3 C3_3 C2_3 122.3(2) . . ?
C4_3 C3_3 H3_3 118.9 . . ?
C2_3 C3_3 H3_3 118.9 . . ?
C3_3 C4_3 C5_3 117.0(2) . . ?
C3_3 C4_3 C8_3 121.7(2) . . ?
C5_3 C4_3 C8_3 121.3(2) . . ?
C4_3 C5_3 C6_3 122.3(2) . . ?
C4_3 C5_3 H5_3 118.8 . . ?
C6_3 C5_3 H5_3 118.8 . . ?
C5_3 C6_3 C1_3 121.4(2) . . ?
C5_3 C6_3 C9_3 116.2(2) . . ?
C1_3 C6_3 C9_3 122.4(2) . . ?
C2_3 C7_3 H7A_3 109.5 . . ?
C2_3 C7_3 H7B_3 109.5 . . ?
H7A_3 C7_3 H7B_3 109.5 . . ?
C2_3 C7_3 H7C_3 109.5 . . ?
H7A_3 C7_3 H7C_3 109.5 . . ?
H7B_3 C7_3 H7C_3 109.5 . . ?
C4_3 C8_3 H8A_3 109.5 . . ?
C4_3 C8_3 H8B_3 109.5 . . ?
H8A_3 C8_3 H8B_3 109.5 . . ?
C4_3 C8_3 H8C_3 109.5 . . ?
H8A_3 C8_3 H8C_3 109.5 . . ?
H8B_3 C8_3 H8C_3 109.5 . . ?
C6_3 C9_3 H9A_3 109.5 . . ?
C6_3 C9_3 H9B_3 109.5 . . ?
H9A_3 C9_3 H9B_3 109.5 . . ?
C6_3 C9_3 H9C_3 109.5 . . ?
H9A_3 C9_3 H9C_3 109.5 . . ?
H9B_3 C9_3 H9C_3 109.5 . . ?
C2_4 N1_4 C6_4 117.0(2) . . ?
C2_4 N1_4 B1_1 123.35(18) . . ?
C6_4 N1_4 B1_1 119.60(18) . . ?
N1_4 C2_4 C3_4 123.9(2) . . ?
N1_4 C2_4 H2_4 118.1 . . ?
C3_4 C2_4 H2_4 118.1 . . ?
C2_4 C3_4 C4_4 119.3(2) . . ?
C2_4 C3_4 H3_4 120.3 . . ?
C4_4 C3_4 H3_4 120.3 . . ?
N7_4 C4_4 C5_4 122.2(2) . . ?
N7_4 C4_4 C3_4 121.8(2) . . ?
C5_4 C4_4 C3_4 115.9(2) . . ?
C6_4 C5_4 C4_4 120.6(2) . . ?
C6_4 C5_4 H5_4 119.7 . . ?
C4_4 C5_4 H5_4 119.7 . . ?
N1_4 C6_4 C5_4 123.2(2) . . ?
N1_4 C6_4 H6_4 118.4 . . ?
C5_4 C6_4 H6_4 118.4 . . ?
C4_4 N7_4 C8_4 121.1(2) . . ?
C4_4 N7_4 C9_4 120.4(2) . . ?
C8_4 N7_4 C9_4 118.1(2) . . ?
N7_4 C8_4 H8A_4 109.5 . . ?
N7_4 C8_4 H8B_4 109.5 . . ?
H8A_4 C8_4 H8B_4 109.5 . . ?
N7_4 C8_4 H8C_4 109.5 . . ?
H8A_4 C8_4 H8C_4 109.5 . . ?
H8B_4 C8_4 H8C_4 109.5 . . ?
N7_4 C9_4 H9A_4 109.5 . . ?
N7_4 C9_4 H9B_4 109.5 . . ?
H9A_4 C9_4 H9B_4 109.5 . . ?
N7_4 C9_4 H9C_4 109.5 . . ?
H9A_4 C9_4 H9C_4 109.5 . . ?
H9B_4 C9_4 H9C_4 109.5 . . ?
C6_5 N1_5 C2_5 116.93(19) . . ?
C6_5 N1_5 B2_1 122.52(18) . . ?
C2_5 N1_5 B2_1 120.35(18) . . ?
N1_5 C2_5 C3_5 123.4(2) . . ?
N1_5 C2_5 H2_5 118.3 . . ?
C3_5 C2_5 H2_5 118.3 . . ?
C2_5 C3_5 C4_5 120.4(2) . . ?
C2_5 C3_5 H3_5 119.8 . . ?
C4_5 C3_5 H3_5 119.8 . . ?
N7_5 C4_5 C5_5 123.0(2) . . ?
N7_5 C4_5 C3_5 121.7(2) . . ?
C5_5 C4_5 C3_5 115.4(2) . . ?
C6_5 C5_5 C4_5 120.4(2) . . ?
C6_5 C5_5 H5_5 119.8 . . ?
C4_5 C5_5 H5_5 119.8 . . ?
N1_5 C6_5 C5_5 123.4(2) . . ?
N1_5 C6_5 H6_5 118.3 . . ?
C5_5 C6_5 H6_5 118.3 . . ?
C4_5 N7_5 C9_5 121.1(2) . . ?
C4_5 N7_5 C8_5 120.5(2) . . ?
C9_5 N7_5 C8_5 118.3(2) . . ?
N7_5 C8_5 H8A_5 109.5 . . ?
N7_5 C8_5 H8B_5 109.5 . . ?
H8A_5 C8_5 H8B_5 109.5 . . ?
N7_5 C8_5 H8C_5 109.5 . . ?
H8A_5 C8_5 H8C_5 109.5 . . ?
H8B_5 C8_5 H8C_5 109.5 . . ?
N7_5 C9_5 H9A_5 109.5 . . ?
N7_5 C9_5 H9B_5 109.5 . . ?
H9A_5 C9_5 H9B_5 109.5 . . ?
N7_5 C9_5 H9C_5 109.5 . . ?
H9A_5 C9_5 H9C_5 109.5 . . ?
H9B_5 C9_5 H9C_5 109.5 . . ?
Cl3_6 C1_6 Cl2_6 112.77(19) . . ?
Cl3_6 C1_6 H1A_6 109.0 . . ?
Cl2_6 C1_6 H1A_6 109.0 . . ?
Cl3_6 C1_6 H1B_6 109.0 . . ?
Cl2_6 C1_6 H1B_6 109.0 . . ?
H1A_6 C1_6 H1B_6 107.8 . . ?

_refine_diff_density_max         1.455
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.093

