# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mo_150929_0m
_database_code_depnum_ccdc_archive 'CCDC 1434531'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 B F4 N'
_chemical_formula_weight         361.18

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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 '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                   9.0489(7)
_cell_length_b                   10.2453(9)
_cell_length_c                   10.8052(9)
_cell_angle_alpha                78.224(2)
_cell_angle_beta                 65.746(2)
_cell_angle_gamma                73.570(2)
_cell_volume                     871.59(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1780
_cell_measurement_theta_min      2.7908
_cell_measurement_theta_max      22.0267

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9064
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12209
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.078
_diffrn_reflns_theta_max         26.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3512
_reflns_number_gt                1342
_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 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1795P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3512
_refine_ls_number_parameters     283
_refine_ls_number_restraints     255
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2990
_refine_ls_wR_factor_gt          0.2507
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      1.107
_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
C1 C 0.3809(5) 0.6370(4) 0.6622(4) 0.0684(11) Uani 1 1 d . . . . .
H1 H 0.4588 0.6048 0.5739 0.082 Uiso 1 1 calc R U . . .
C2 C 0.2818(6) 0.7787(4) 0.6333(5) 0.0839(14) Uani 1 1 d . . . . .
H2A H 0.3532 0.8433 0.6007 0.101 Uiso 1 1 calc R U . . .
H2B H 0.2434 0.7769 0.5622 0.101 Uiso 1 1 calc R U . . .
C3 C 0.1340(6) 0.8255(4) 0.7595(5) 0.0877(14) Uani 1 1 d . . . . .
H3A H 0.1721 0.8308 0.8298 0.105 Uiso 1 1 calc R U . . .
H3B H 0.0736 0.9159 0.7381 0.105 Uiso 1 1 calc R U . . .
C4 C -0.1390(6) 0.7763(5) 0.8716(5) 0.0842(13) Uani 1 1 d . . . . .
H4 H -0.1792 0.8696 0.8797 0.101 Uiso 1 1 calc R U . . .
C5 C -0.2490(6) 0.6910(6) 0.9238(4) 0.0870(14) Uani 1 1 d . . . . .
H5 H -0.3622 0.7262 0.9671 0.104 Uiso 1 1 calc R U . . .
C6 C -0.1908(6) 0.5573(6) 0.9115(4) 0.0816(13) Uani 1 1 d . . . . .
H6 H -0.2646 0.4995 0.9455 0.098 Uiso 1 1 calc R U . . .
C7 C -0.0187(5) 0.5019(4) 0.8477(4) 0.0666(11) Uani 1 1 d . . . . .
C8 C 0.0493(6) 0.3595(5) 0.8360(4) 0.0780(13) Uani 1 1 d . . . . .
H8 H -0.0216 0.2993 0.8698 0.094 Uiso 1 1 calc R U . . .
C9 C 0.2164(6) 0.3098(4) 0.7760(4) 0.0742(12) Uani 1 1 d . . . . .
C10 C 0.3194(5) 0.4036(4) 0.7235(4) 0.0691(11) Uani 1 1 d . . . . .
H10 H 0.4334 0.3699 0.6824 0.083 Uiso 1 1 calc R U . . .
C11 C 0.2630(5) 0.5402(4) 0.7290(4) 0.0613(10) Uani 1 1 d . . . . .
C12 C 0.0899(5) 0.5918(4) 0.7950(3) 0.0579(10) Uani 1 1 d . . . . .
C13 C 0.2868(7) 0.1600(5) 0.7654(6) 0.1088(17) Uani 1 1 d . . . . .
H13A H 0.3381 0.1432 0.6711 0.163 Uiso 1 1 calc R U . . .
H13B H 0.1993 0.1114 0.8119 0.163 Uiso 1 1 calc R U . . .
H13C H 0.3684 0.1291 0.8065 0.163 Uiso 1 1 calc R U . . .
C14 C 0.4826(5) 0.6338(4) 0.7446(4) 0.0716(12) Uani 1 1 d . . . . .
H14A H 0.5288 0.5394 0.7697 0.086 Uiso 1 1 calc R U . . .
H14B H 0.4106 0.6761 0.8279 0.086 Uiso 1 1 calc R U . . .
C15 C 0.6233(6) 0.7077(4) 0.6664(4) 0.0687(11) Uani 1 1 d . . . . .
C16 C 0.7705(6) 0.6442(5) 0.5705(5) 0.0805(13) Uani 1 1 d . . . . .
H16 H 0.7833 0.5553 0.5538 0.097 Uiso 1 1 calc R U . . .
C17 C 0.8980(6) 0.7113(6) 0.4996(5) 0.0933(15) Uani 1 1 d . . . . .
H17 H 0.9973 0.6672 0.4370 0.112 Uiso 1 1 calc R U . . .
C18 C 0.8777(7) 0.8436(6) 0.5218(5) 0.0915(15) Uani 1 1 d . . . . .
H18 H 0.9635 0.8891 0.4735 0.110 Uiso 1 1 calc R U . . .
C19 C 0.7349(7) 0.9080(5) 0.6129(5) 0.0884(14) Uani 1 1 d . . . . .
H19 H 0.7214 0.9979 0.6269 0.106 Uiso 1 1 calc R U . . .
C20 C 0.6081(6) 0.8394(4) 0.6855(5) 0.0774(12) Uani 1 1 d . . . . .
H20 H 0.5101 0.8841 0.7488 0.093 Uiso 1 1 calc R U . . .
N1 N 0.0221(4) 0.7283(3) 0.8103(3) 0.0676(9) Uani 1 1 d . . . . .
B1 B 0.7214(14) 0.1842(12) 0.8519(13) 0.101(3) Uani 0.560(7) 1 d D U P A 1
F1 F 0.8640(8) 0.1117(7) 0.8309(11) 0.149(3) Uani 0.560(7) 1 d D U P A 1
F2 F 0.7065(9) 0.2420(10) 0.7316(8) 0.177(3) Uani 0.560(7) 1 d D U P A 1
F3 F 0.6670(14) 0.2738(11) 0.9296(10) 0.159(3) Uani 0.560(7) 1 d D U P A 1
F4 F 0.6283(12) 0.0934(11) 0.8776(12) 0.199(4) Uani 0.560(7) 1 d D U P A 1
B1' B 0.7125(18) 0.1767(13) 0.8783(14) 0.107(3) Uani 0.440(7) 1 d D U P A 2
F1' F 0.7896(13) 0.1264(9) 0.9558(12) 0.156(3) Uani 0.440(7) 1 d D U P A 2
F2' F 0.7888(16) 0.1302(14) 0.7662(11) 0.184(4) Uani 0.440(7) 1 d D U P A 2
F3' F 0.654(2) 0.3034(12) 0.8761(15) 0.152(4) Uani 0.440(7) 1 d D U P A 2
F4' F 0.5784(14) 0.1134(17) 0.9369(15) 0.212(5) Uani 0.440(7) 1 d 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
C1 C14 1.511(5) . ?
C1 C11 1.522(5) . ?
C1 C2 1.522(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.511(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.485(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.319(6) . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.334(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(6) . ?
C6 H6 0.9300 . ?
C7 C12 1.405(5) . ?
C7 C8 1.424(6) . ?
C8 C9 1.364(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(5) . ?
C9 C13 1.494(6) . ?
C10 C11 1.352(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(5) . ?
C12 N1 1.373(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.520(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.366(5) . ?
C15 C16 1.387(6) . ?
C16 C17 1.378(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.346(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
B1 F3 1.228(10) . ?
B1 F1 1.247(10) . ?
B1 F4 1.341(11) . ?
B1 F2 1.357(11) . ?
B1' F2' 1.238(12) . ?
B1' F1' 1.247(12) . ?
B1' F3' 1.255(11) . ?
B1' F4' 1.393(12) . ?

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
C14 C1 C11 111.9(3) . . ?
C14 C1 C2 114.3(3) . . ?
C11 C1 C2 108.8(3) . . ?
C14 C1 H1 107.2 . . ?
C11 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
C3 C2 C1 111.5(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C2 110.1(4) . . ?
N1 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C5 121.4(5) . . ?
N1 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.1(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C12 C7 C6 118.3(4) . . ?
C12 C7 C8 118.7(4) . . ?
C6 C7 C8 123.0(4) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.0(4) . . ?
C8 C9 C13 120.9(4) . . ?
C10 C9 C13 121.2(4) . . ?
C11 C10 C9 123.9(4) . . ?
C11 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C10 C11 C12 118.3(4) . . ?
C10 C11 C1 121.1(4) . . ?
C12 C11 C1 120.6(4) . . ?
N1 C12 C7 117.8(4) . . ?
N1 C12 C11 122.4(4) . . ?
C7 C12 C11 119.8(4) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C15 112.2(3) . . ?
C1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C20 C15 C16 117.8(4) . . ?
C20 C15 C14 121.5(4) . . ?
C16 C15 C14 120.7(4) . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.6(5) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.5(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 121.7(5) . . ?
C15 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C4 N1 C12 122.3(4) . . ?
C4 N1 C3 118.6(4) . . ?
C12 N1 C3 119.1(3) . . ?
F3 B1 F1 119.2(11) . . ?
F3 B1 F4 117.1(11) . . ?
F1 B1 F4 103.6(9) . . ?
F3 B1 F2 108.3(10) . . ?
F1 B1 F2 110.1(10) . . ?
F4 B1 F2 96.0(9) . . ?
F2' B1' F1' 110.6(12) . . ?
F2' B1' F3' 116.5(13) . . ?
F1' B1' F3' 116.1(11) . . ?
F2' B1' F4' 102.6(10) . . ?
F1' B1' F4' 101.5(11) . . ?
F3' B1' F4' 107.3(14) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_a16581a
_database_code_depnum_ccdc_archive 'CCDC 1434532'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H24 N2'
_chemical_formula_sum            'C32 H24 N2'
_chemical_formula_weight         436.53

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   7.917(6)
_cell_length_b                   22.675(14)
_cell_length_c                   25.49(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4577(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19221
_diffrn_reflns_av_R_equivalents  0.1883
_diffrn_reflns_av_sigmaI/netI    0.4043
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4006
_reflns_number_gt                1068
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4006
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3434
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.2222
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5328(9) 0.2436(3) 0.1496(3) 0.045(2) Uani 1 1 d . . .
H1 H 0.5188 0.2243 0.1168 0.054 Uiso 1 1 calc R . .
C2 C 0.5937(8) 0.3035(3) 0.1495(3) 0.043(2) Uani 1 1 d . . .
H2 H 0.6116 0.3239 0.1174 0.051 Uiso 1 1 calc R . .
C3 C 0.6257(8) 0.3305(3) 0.1971(3) 0.0308(19) Uani 1 1 d . . .
C4 C 0.6864(10) 0.3936(3) 0.1942(3) 0.039(2) Uani 1 1 d . . .
C5 C 0.8037(9) 0.4112(3) 0.1560(3) 0.042(2) Uani 1 1 d . . .
H5 H 0.8482 0.3829 0.1323 0.050 Uiso 1 1 calc R . .
C6 C 0.8550(9) 0.4694(3) 0.1526(3) 0.048(2) Uani 1 1 d . . .
H6 H 0.9351 0.4806 0.1267 0.057 Uiso 1 1 calc R . .
C7 C 0.7916(9) 0.5107(3) 0.1860(3) 0.045(2) Uani 1 1 d . . .
H7 H 0.8281 0.5505 0.1833 0.054 Uiso 1 1 calc R . .
C8 C 0.6746(10) 0.4953(3) 0.2238(3) 0.044(2) Uani 1 1 d . . .
H8 H 0.6315 0.5242 0.2472 0.053 Uiso 1 1 calc R . .
C9 C 0.6195(9) 0.4361(3) 0.2275(3) 0.036(2) Uani 1 1 d . . .
H9 H 0.5367 0.4254 0.2527 0.043 Uiso 1 1 calc R . .
C10 C 0.5978(9) 0.2982(3) 0.2438(3) 0.0310(19) Uani 1 1 d . . .
C11 C 0.5250(9) 0.2404(3) 0.2394(3) 0.0347(19) Uani 1 1 d . . .
C12 C 0.4805(8) 0.2098(3) 0.2859(3) 0.035(2) Uani 1 1 d . . .
C13 C 0.3961(9) 0.1505(3) 0.2811(3) 0.051(2) Uani 1 1 d . . .
H13A H 0.3797 0.1410 0.2440 0.077 Uiso 1 1 calc R . .
H13B H 0.2863 0.1516 0.2988 0.077 Uiso 1 1 calc R . .
H13C H 0.4675 0.1203 0.2975 0.077 Uiso 1 1 calc R . .
C14 C 0.5196(9) 0.2323(3) 0.3334(3) 0.038(2) Uani 1 1 d . . .
H14 H 0.4861 0.2115 0.3641 0.046 Uiso 1 1 calc R . .
C15 C 0.6107(9) 0.2871(3) 0.3388(3) 0.035(2) Uani 1 1 d . . .
C16 C 0.6455(8) 0.3190(3) 0.2939(3) 0.036(2) Uani 1 1 d . . .
H16 H 0.7026 0.3557 0.2967 0.043 Uiso 1 1 calc R . .
C17 C 0.6691(8) 0.3051(3) 0.3929(3) 0.0331(19) Uani 1 1 d . . .
C18 C 0.7047(9) 0.2621(3) 0.4313(3) 0.040(2) Uani 1 1 d . . .
H18 H 0.6893 0.2218 0.4222 0.048 Uiso 1 1 calc R . .
C19 C 0.7595(9) 0.2745(3) 0.4805(3) 0.038(2) Uani 1 1 d . . .
C20 C 0.7840(9) 0.2264(3) 0.5199(3) 0.052(2) Uani 1 1 d . . .
H20A H 0.8246 0.2433 0.5530 0.078 Uiso 1 1 calc R . .
H20B H 0.8673 0.1981 0.5067 0.078 Uiso 1 1 calc R . .
H20C H 0.6763 0.2062 0.5260 0.078 Uiso 1 1 calc R . .
C21 C 0.7867(9) 0.3354(3) 0.4943(3) 0.041(2) Uani 1 1 d . . .
C22 C 0.7560(8) 0.3802(3) 0.4569(3) 0.0322(19) Uani 1 1 d . . .
C23 C 0.6939(8) 0.3648(3) 0.4064(3) 0.039(2) Uani 1 1 d . . .
H23 H 0.6690 0.3949 0.3816 0.046 Uiso 1 1 calc R . .
C24 C 0.7812(8) 0.4412(3) 0.4723(3) 0.038(2) Uani 1 1 d . . .
C25 C 0.7544(9) 0.4923(3) 0.4362(3) 0.036(2) Uani 1 1 d . . .
C26 C 0.8274(9) 0.4952(3) 0.3868(3) 0.039(2) Uani 1 1 d . . .
H26 H 0.8973 0.4638 0.3751 0.047 Uiso 1 1 calc R . .
C27 C 0.8001(9) 0.5432(3) 0.3543(3) 0.050(2) Uani 1 1 d . . .
H27 H 0.8513 0.5444 0.3206 0.061 Uiso 1 1 calc R . .
C28 C 0.6963(10) 0.5903(3) 0.3709(4) 0.053(2) Uani 1 1 d . . .
H28 H 0.6748 0.6228 0.3483 0.064 Uiso 1 1 calc R . .
C29 C 0.6269(10) 0.5883(3) 0.4206(4) 0.055(2) Uani 1 1 d . . .
H29 H 0.5604 0.6204 0.4327 0.066 Uiso 1 1 calc R . .
C30 C 0.6532(9) 0.5395(3) 0.4531(3) 0.050(2) Uani 1 1 d . . .
H30 H 0.6025 0.5383 0.4869 0.060 Uiso 1 1 calc R . .
C31 C 0.8312(10) 0.4501(3) 0.5228(3) 0.053(2) Uani 1 1 d . . .
H31 H 0.8482 0.4893 0.5348 0.064 Uiso 1 1 calc R . .
C32 C 0.8587(10) 0.4030(3) 0.5579(3) 0.057(3) Uani 1 1 d . . .
H32 H 0.8945 0.4121 0.5925 0.069 Uiso 1 1 calc R . .
N1 N 0.4951(7) 0.2139(2) 0.1928(3) 0.0414(17) Uani 1 1 d . . .
N2 N 0.8371(8) 0.3465(3) 0.5451(3) 0.0533(19) 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
C1 N1 1.325(8) . ?
C1 C2 1.441(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(8) . ?
C2 H2 0.9500 . ?
C3 C10 1.414(8) . ?
C3 C4 1.511(8) . ?
C4 C9 1.389(8) . ?
C4 C5 1.403(8) . ?
C5 C6 1.384(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.362(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.413(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C16 1.412(8) . ?
C10 C11 1.437(8) . ?
C11 N1 1.352(8) . ?
C11 C12 1.418(9) . ?
C12 C14 1.352(8) . ?
C12 C13 1.506(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.443(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(8) . ?
C15 C17 1.511(9) . ?
C16 H16 0.9500 . ?
C17 C23 1.410(8) . ?
C17 C18 1.411(8) . ?
C18 C19 1.356(8) . ?
C18 H18 0.9500 . ?
C19 C21 1.441(8) . ?
C19 C20 1.496(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N2 1.379(8) . ?
C21 C22 1.415(8) . ?
C22 C23 1.423(8) . ?
C22 C24 1.450(8) . ?
C23 H23 0.9500 . ?
C24 C31 1.362(8) . ?
C24 C25 1.495(9) . ?
C25 C26 1.386(8) . ?
C25 C30 1.405(8) . ?
C26 C27 1.385(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.413(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(8) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.408(8) . ?
C31 H31 0.9500 . ?
C32 N2 1.333(7) . ?
C32 H32 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
N1 C1 C2 123.7(7) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 118.5(7) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C10 118.7(6) . . ?
C2 C3 C4 115.8(6) . . ?
C10 C3 C4 125.5(6) . . ?
C9 C4 C5 118.6(7) . . ?
C9 C4 C3 120.4(7) . . ?
C5 C4 C3 120.9(7) . . ?
C6 C5 C4 120.6(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.5(7) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.7(7) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.5(7) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C4 C9 C8 120.0(7) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C16 C10 C3 123.1(6) . . ?
C16 C10 C11 118.8(6) . . ?
C3 C10 C11 118.0(6) . . ?
N1 C11 C12 118.2(7) . . ?
N1 C11 C10 123.0(7) . . ?
C12 C11 C10 118.8(7) . . ?
C14 C12 C11 120.5(7) . . ?
C14 C12 C13 120.7(7) . . ?
C11 C12 C13 118.7(7) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 121.7(7) . . ?
C12 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 118.1(7) . . ?
C16 C15 C17 123.6(6) . . ?
C14 C15 C17 118.2(6) . . ?
C15 C16 C10 121.4(7) . . ?
C15 C16 H16 119.3 . . ?
C10 C16 H16 119.3 . . ?
C23 C17 C18 117.9(7) . . ?
C23 C17 C15 121.6(6) . . ?
C18 C17 C15 120.4(6) . . ?
C19 C18 C17 124.1(7) . . ?
C19 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?
C18 C19 C21 118.3(7) . . ?
C18 C19 C20 120.7(6) . . ?
C21 C19 C20 121.0(7) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 123.5(7) . . ?
N2 C21 C19 116.7(7) . . ?
C22 C21 C19 119.8(7) . . ?
C21 C22 C23 119.6(6) . . ?
C21 C22 C24 118.6(7) . . ?
C23 C22 C24 121.8(6) . . ?
C17 C23 C22 120.3(6) . . ?
C17 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C31 C24 C22 115.9(7) . . ?
C31 C24 C25 120.6(7) . . ?
C22 C24 C25 123.6(7) . . ?
C26 C25 C30 118.7(7) . . ?
C26 C25 C24 122.4(7) . . ?
C30 C25 C24 118.9(7) . . ?
C27 C26 C25 121.0(7) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 120.4(7) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 118.7(8) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C30 120.7(8) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 120.4(8) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C24 C31 C32 122.2(7) . . ?
C24 C31 H31 118.9 . . ?
C32 C31 H31 118.9 . . ?
N2 C32 C31 123.6(7) . . ?
N2 C32 H32 118.2 . . ?
C31 C32 H32 118.2 . . ?
C1 N1 C11 117.7(6) . . ?
C32 N2 C21 116.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_140445LT_a
_database_code_depnum_ccdc_archive 'CCDC 1434533'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H36 B2 F8 N2'
_chemical_formula_weight         814.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   13.2275(13)
_cell_length_b                   12.9049(11)
_cell_length_c                   12.2015(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.482(6)
_cell_angle_gamma                90
_cell_volume                     1951.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    729
_cell_measurement_theta_min      3.5669
_cell_measurement_theta_max      32.1474

_exptl_crystal_description       Lump
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.897
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13094
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.567
_diffrn_reflns_theta_max         66.746
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             3356
_reflns_number_gt                657
_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 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_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)+(0.1438P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3356
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2009
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2861
_refine_ls_wR_factor_gt          0.2190
_refine_ls_goodness_of_fit_ref   0.670
_refine_ls_restrained_S_all      0.670
_refine_ls_shift/su_max          0.004
_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 B 0.1946(18) 0.1088(14) 0.7459(15) 0.253(9) Uani 1 1 d . . . . .
C1 C 0.0319(10) 0.2988(8) 0.9295(8) 0.217(4) Uani 1 1 d . . . . .
H1A H 0.0035 0.3576 0.9623 0.260 Uiso 1 1 calc R U . . .
H1B H 0.0655 0.2495 0.9942 0.260 Uiso 1 1 calc R U . . .
C2 C -0.0579(9) 0.2477(6) 0.8438(10) 0.198(4) Uani 1 1 d . . . . .
H2 H -0.0821 0.1802 0.8534 0.238 Uiso 1 1 calc R U . . .
C3 C -0.1079(8) 0.3124(7) 0.7394(10) 0.198(3) Uani 1 1 d . . . . .
H3 H -0.1465 0.3678 0.7666 0.238 Uiso 1 1 calc R U . . .
C4 C -0.0233(7) 0.3709(5) 0.7053(8) 0.147(2) Uani 1 1 d . . . . .
C5 C -0.0545(5) 0.4183(5) 0.5972(7) 0.139(2) Uani 1 1 d . . . . .
H5 H -0.1278 0.4139 0.5472 0.167 Uiso 1 1 calc R U . . .
C6 C 0.0197(6) 0.4737(4) 0.5583(5) 0.125(2) Uani 1 1 d . . . . .
C7 C 0.1246(6) 0.4716(5) 0.6283(7) 0.133(2) Uani 1 1 d . . . . .
H7 H 0.1766 0.5027 0.6013 0.159 Uiso 1 1 calc R U . . .
C8 C 0.1597(7) 0.4255(5) 0.7392(7) 0.136(2) Uani 1 1 d . . . . .
C9 C 0.2711(8) 0.4239(6) 0.8113(9) 0.158(3) Uani 1 1 d . . . . .
C10 C 0.2978(8) 0.3801(8) 0.9192(9) 0.181(3) Uani 1 1 d . . . . .
H10 H 0.3716 0.3738 0.9671 0.218 Uiso 1 1 calc R U . . .
C11 C 0.2190(11) 0.3449(7) 0.9598(8) 0.180(3) Uani 1 1 d . . . . .
H11 H 0.2389 0.3251 1.0396 0.216 Uiso 1 1 calc R U . . .
C12 C 0.0805(8) 0.3769(5) 0.7783(8) 0.139(2) Uani 1 1 d . . . . .
C13 C -0.1964(11) 0.2620(8) 0.6354(10) 0.168(3) Uani 1 1 d . . . . .
C14 C -0.1767(10) 0.1791(10) 0.5750(12) 0.202(4) Uani 1 1 d . . . . .
H14 H -0.1081 0.1463 0.6025 0.243 Uiso 1 1 calc R U . . .
C15 C -0.2537(16) 0.1436(11) 0.4771(15) 0.235(7) Uani 1 1 d . . . . .
H15 H -0.2366 0.0912 0.4318 0.282 Uiso 1 1 calc R U . . .
C16 C -0.3557(15) 0.1824(14) 0.4430(14) 0.248(7) Uani 1 1 d . . . . .
H16 H -0.4112 0.1513 0.3794 0.298 Uiso 1 1 calc R U . . .
C17 C -0.3787(10) 0.2637(12) 0.4978(14) 0.215(4) Uani 1 1 d . . . . .
H17 H -0.4485 0.2942 0.4699 0.258 Uiso 1 1 calc R U . . .
C18 C -0.2996(13) 0.3023(7) 0.5951(11) 0.185(3) Uani 1 1 d . . . . .
H18 H -0.3163 0.3585 0.6361 0.222 Uiso 1 1 calc R U . . .
C19 C 0.3557(7) 0.4595(9) 0.7677(9) 0.170(3) Uani 1 1 d . . . . .
C20 C 0.4164(11) 0.5387(9) 0.8161(8) 0.207(4) Uani 1 1 d . . . . .
H20 H 0.4038 0.5732 0.8789 0.248 Uiso 1 1 calc R U . . .
C21 C 0.4976(11) 0.5743(12) 0.7802(9) 0.246(6) Uani 1 1 d . . . . .
H21 H 0.5408 0.6316 0.8181 0.295 Uiso 1 1 calc R U . . .
C22 C 0.5141(8) 0.5285(12) 0.6941(12) 0.226(6) Uani 1 1 d . . . . .
H22 H 0.5723 0.5511 0.6715 0.271 Uiso 1 1 calc R U . . .
C23 C 0.4490(10) 0.4458(11) 0.6321(10) 0.247(5) Uani 1 1 d . . . . .
H23 H 0.4600 0.4134 0.5673 0.296 Uiso 1 1 calc R U . . .
C24 C 0.3674(7) 0.4152(8) 0.6727(11) 0.230(5) Uani 1 1 d . . . . .
H24 H 0.3190 0.3619 0.6327 0.276 Uiso 1 1 calc R U . . .
F1 F 0.2074(5) 0.1021(4) 0.8602(5) 0.277(3) Uani 1 1 d . . . . .
F2 F 0.2208(5) 0.0316(4) 0.7103(6) 0.279(3) Uani 1 1 d . . . . .
F3 F 0.0862(6) 0.1097(9) 0.6981(7) 0.387(6) Uani 1 1 d . . . . .
F4 F 0.2275(7) 0.1934(4) 0.7172(5) 0.287(4) Uani 1 1 d . . . . .
N1 N 0.1144(8) 0.3376(5) 0.8896(8) 0.163(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 F2 1.186(13) . ?
B1 F4 1.27(2) . ?
B1 F3 1.35(2) . ?
B1 F1 1.347(13) . ?
C1 N1 1.432(9) . ?
C1 C2 1.439(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.471(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.523(9) . ?
C3 C13 1.538(10) . ?
C3 H3 1.0000 . ?
C4 C12 1.353(8) . ?
C4 C5 1.380(8) . ?
C5 C6 1.423(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.351(7) . ?
C6 C6 1.496(10) 3_566 ?
C7 C8 1.399(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.429(8) . ?
C8 C12 1.438(8) . ?
C9 C10 1.360(9) . ?
C9 C19 1.470(11) . ?
C10 C11 1.378(10) . ?
C10 H10 0.9500 . ?
C11 N1 1.352(8) . ?
C11 H11 0.9500 . ?
C12 N1 1.370(8) . ?
C13 C14 1.374(11) . ?
C13 C18 1.380(9) . ?
C14 C15 1.350(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.360(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.335(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(12) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.306(10) . ?
C19 C24 1.349(10) . ?
C20 C21 1.373(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.289(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.413(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(12) . ?
C23 H23 0.9500 . ?
C24 H24 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
F2 B1 F4 116.7(14) . . ?
F2 B1 F3 105(2) . . ?
F4 B1 F3 106.8(9) . . ?
F2 B1 F1 112.2(11) . . ?
F4 B1 F1 114.2(19) . . ?
F3 B1 F1 100.3(12) . . ?
N1 C1 C2 116.5(8) . . ?
N1 C1 H1A 108.2 . . ?
C2 C1 H1A 108.2 . . ?
N1 C1 H1B 108.2 . . ?
C2 C1 H1B 108.2 . . ?
H1A C1 H1B 107.3 . . ?
C1 C2 C3 112.1(8) . . ?
C1 C2 H2 124.0 . . ?
C3 C2 H2 124.0 . . ?
C2 C3 C4 111.5(9) . . ?
C2 C3 C13 117.1(9) . . ?
C4 C3 C13 113.8(8) . . ?
C2 C3 H3 104.2 . . ?
C4 C3 H3 104.2 . . ?
C13 C3 H3 104.2 . . ?
C12 C4 C5 119.9(8) . . ?
C12 C4 C3 121.5(9) . . ?
C5 C4 C3 118.6(9) . . ?
C4 C5 C6 122.1(7) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.0(6) . . ?
C7 C6 C6 123.4(8) . 3_566 ?
C5 C6 C6 119.6(9) . 3_566 ?
C6 C7 C8 122.7(7) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C9 121.6(9) . . ?
C7 C8 C12 118.2(8) . . ?
C9 C8 C12 120.2(9) . . ?
C10 C9 C8 117.7(10) . . ?
C10 C9 C19 120.5(10) . . ?
C8 C9 C19 121.6(9) . . ?
C9 C10 C11 120.9(11) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N1 C11 C10 122.0(10) . . ?
N1 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C4 C12 N1 122.4(10) . . ?
C4 C12 C8 119.7(9) . . ?
N1 C12 C8 117.9(9) . . ?
C14 C13 C18 116.8(11) . . ?
C14 C13 C3 122.7(14) . . ?
C18 C13 C3 120.4(11) . . ?
C15 C14 C13 120.8(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.5(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.7(18) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 118.7(14) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C13 122.1(11) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
C20 C19 C24 118.9(11) . . ?
C20 C19 C9 120.4(12) . . ?
C24 C19 C9 120.6(10) . . ?
C19 C20 C21 122.9(12) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C22 C21 C20 118.7(16) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 122.5(15) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C24 C23 C22 115.3(11) . . ?
C24 C23 H23 122.4 . . ?
C22 C23 H23 122.4 . . ?
C19 C24 C23 121.4(11) . . ?
C19 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C11 N1 C12 120.6(9) . . ?
C11 N1 C1 122.8(10) . . ?
C12 N1 C1 116.3(9) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

