 
data_08132016-1
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C25 H31 B F2 N4 O3, C7 H8'
_chemical_formula_sum
 'C32 H39 B F2 N4 O3' 
_chemical_formula_weight          576.48

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'
 'O'  'O'   0.0492   0.0322
 '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                    15.1030(5)
_cell_length_b                    12.2789(3)
_cell_length_c                    16.4063(12)
_cell_angle_alpha                 90
_cell_angle_beta                  95.270(7)
_cell_angle_gamma                 90
_cell_volume                      3029.7(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used           8647
_cell_measurement_theta_min             2.9
_cell_measurement_theta_max             66.5
 
_exptl_crystal_description              'Platelet'
_exptl_crystal_colour                   'Red'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.264          
_exptl_crystal_F_000              1224
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max                 0.15
_exptl_crystal_size_mid                 0.15
_exptl_crystal_size_min                 0.10
_exptl_absorpt_coefficient_mu     0.732
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_max         1.000
_exptl_absorpt_correction_T_min         0.476
_exptl_absorpt_process_details    
;
FS_PROCESS, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      1.54187
_diffrn_radiation_type            CuK\a
_diffrn_source                          'Sealed Tube'
_diffrn_radiation_monochromator         'Graphite Monochromator'
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean        10.0000
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_reflns_number             17365
_diffrn_reflns_av_unetI/netI      0.1659
_diffrn_reflns_av_R_equivalents   0.1112
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.938
_diffrn_reflns_theta_max          58.936
_diffrn_reflns_theta_full         58.936
_diffrn_measured_fraction_theta_max   0.989
_diffrn_measured_fraction_theta_full  0.989
_diffrn_reflns_Laue_measured_fraction_max    0.989
_diffrn_reflns_Laue_measured_fraction_full   0.989
_diffrn_reflns_point_group_measured_fraction_max   0.989
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              4307
_reflns_number_gt                 1392
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1350P)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          4307
_refine_ls_number_parameters      386
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2199
_refine_ls_R_factor_gt            0.0948
_refine_ls_wR_factor_ref          0.2937
_refine_ls_wR_factor_gt           0.2034
_refine_ls_goodness_of_fit_ref    0.918
_refine_ls_restrained_S_all       0.918
_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 0.0624(2) 0.7504(3) -0.0116(2) 0.0873(12) Uani 1 1 d . . . . .
F2 F 0.1513(2) 0.7640(3) 0.1069(2) 0.0892(12) Uani 1 1 d . . . . .
O1 O -0.2027(3) 0.7116(4) 0.2471(3) 0.0974(16) Uani 1 1 d . . . . .
O2 O 0.3845(3) 0.5517(4) -0.1059(3) 0.0977(16) Uani 1 1 d . . . . .
O3 O 0.3763(3) 0.3814(4) -0.0562(3) 0.0932(15) Uani 1 1 d . . . . .
N1 N 0.0258(4) 0.6404(5) 0.1028(3) 0.0743(16) Uani 1 1 d . . . . .
N2 N 0.1566(4) 0.5988(5) 0.0281(3) 0.0726(16) Uani 1 1 d . . . . .
N3 N -0.2048(4) 0.5272(6) 0.2454(3) 0.0864(18) Uani 1 1 d . . . . .
N4 N -0.0933(4) 0.9861(5) 0.1751(3) 0.0824(17) Uani 1 1 d . . . . .
C1 C -0.0368(5) 0.6952(6) 0.1403(4) 0.077(2) Uani 1 1 d . . . . .
C2 C -0.0926(5) 0.6157(6) 0.1776(4) 0.073(2) Uani 1 1 d . . . . .
C3 C -0.0617(5) 0.5124(7) 0.1597(4) 0.0728(19) Uani 1 1 d . . . . .
C4 C 0.0152(5) 0.5278(6) 0.1141(4) 0.073(2) Uani 1 1 d . . . . .
C5 C 0.0710(5) 0.4546(6) 0.0838(4) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.0597 0.3792 0.0906 0.091 Uiso 1 1 calc R U . . .
C6 C 0.1457(5) 0.4862(6) 0.0421(4) 0.074(2) Uani 1 1 d . . . . .
C7 C 0.2110(5) 0.4260(6) 0.0095(4) 0.0718(19) Uani 1 1 d . . . . .
C8 C 0.2649(5) 0.5030(6) -0.0253(4) 0.076(2) Uani 1 1 d . . . . .
C9 C 0.2315(5) 0.6081(6) -0.0140(4) 0.0717(19) Uani 1 1 d . . . . .
C10 C 0.2653(4) 0.7172(5) -0.0380(4) 0.084(2) Uani 1 1 d . . . . .
H10A H 0.2987 0.7091 -0.0861 0.126 Uiso 1 1 calc R U . . .
H10B H 0.3043 0.7474 0.0075 0.126 Uiso 1 1 calc R U . . .
H10C H 0.2149 0.7665 -0.0510 0.126 Uiso 1 1 calc R U . . .
C11 C 0.2180(4) 0.3052(5) 0.0120(4) 0.084(2) Uani 1 1 d . . . . .
H11A H 0.2253 0.2776 -0.0431 0.127 Uiso 1 1 calc R U . . .
H11B H 0.1638 0.2745 0.0313 0.127 Uiso 1 1 calc R U . . .
H11C H 0.2695 0.2840 0.0493 0.127 Uiso 1 1 calc R U . . .
C12 C 0.3468(5) 0.4860(7) -0.0674(4) 0.077(2) Uani 1 1 d . . . . .
C13 C 0.4577(5) 0.3561(6) -0.0934(4) 0.104(3) Uani 1 1 d . . . . .
H13A H 0.5057 0.4072 -0.0737 0.125 Uiso 1 1 calc R U . . .
H13B H 0.4480 0.3617 -0.1537 0.125 Uiso 1 1 calc R U . . .
C14 C 0.4816(5) 0.2439(6) -0.0687(5) 0.123(3) Uani 1 1 d . . . . .
H14A H 0.5365 0.2229 -0.0921 0.185 Uiso 1 1 calc R U . . .
H14B H 0.4335 0.1944 -0.0887 0.185 Uiso 1 1 calc R U . . .
H14C H 0.4906 0.2396 -0.0089 0.185 Uiso 1 1 calc R U . . .
C15 C -0.1000(5) 0.4152(6) 0.1855(4) 0.079(2) Uani 1 1 d . . . . .
H15 H -0.0765 0.3457 0.1740 0.095 Uiso 1 1 calc R U . . .
C16 C -0.1717(6) 0.4268(7) 0.2273(4) 0.083(2) Uani 1 1 d . . . . .
H16 H -0.2006 0.3635 0.2449 0.100 Uiso 1 1 calc R U . . .
C17 C -0.1693(5) 0.6273(8) 0.2234(4) 0.080(2) Uani 1 1 d . . . . .
C18 C -0.2817(5) 0.5282(5) 0.2953(4) 0.086(2) Uani 1 1 d . . . . .
H18A H -0.3203 0.4646 0.2808 0.104 Uiso 1 1 calc R U . . .
H18B H -0.3172 0.5951 0.2834 0.104 Uiso 1 1 calc R U . . .
C19 C -0.2495(4) 0.5243(5) 0.3867(4) 0.083(2) Uani 1 1 d . . . . .
H19A H -0.2140 0.4574 0.3983 0.099 Uiso 1 1 calc R U . . .
H19B H -0.2106 0.5878 0.4008 0.099 Uiso 1 1 calc R U . . .
C20 C -0.3266(5) 0.5255(5) 0.4390(4) 0.090(2) Uani 1 1 d . . . . .
H20A H -0.3659 0.4626 0.4245 0.108 Uiso 1 1 calc R U . . .
H20B H -0.3616 0.5929 0.4280 0.108 Uiso 1 1 calc R U . . .
C21 C -0.2941(5) 0.5201(5) 0.5310(4) 0.100(2) Uani 1 1 d . . . . .
H21A H -0.3455 0.5158 0.5633 0.150 Uiso 1 1 calc R U . . .
H21B H -0.2595 0.5855 0.5466 0.150 Uiso 1 1 calc R U . . .
H21C H -0.2568 0.4554 0.5416 0.150 Uiso 1 1 calc R U . . .
C22 C -0.0385(4) 0.8085(6) 0.1384(3) 0.078(2) Uani 1 1 d . . . . .
H22 H 0.0036 0.8434 0.1075 0.093 Uiso 1 1 calc R U . . .
C23 C -0.0953(5) 0.8751(6) 0.1769(4) 0.080(2) Uani 1 1 d . . . . .
H23 H -0.1388 0.8413 0.2067 0.096 Uiso 1 1 calc R U . . .
C24 C -0.1584(5) 1.0510(6) 0.2157(4) 0.098(2) Uani 1 1 d . . . . .
H24A H -0.1273 1.1069 0.2499 0.147 Uiso 1 1 calc R U . . .
H24B H -0.1914 1.0033 0.2500 0.147 Uiso 1 1 calc R U . . .
H24C H -0.1999 1.0859 0.1743 0.147 Uiso 1 1 calc R U . . .
C25 C -0.0313(5) 1.0459(5) 0.1281(4) 0.100(2) Uani 1 1 d . . . . .
H25A H -0.0343 1.1238 0.1407 0.151 Uiso 1 1 calc R U . . .
H25B H -0.0474 1.0347 0.0695 0.151 Uiso 1 1 calc R U . . .
H25C H 0.0293 1.0194 0.1426 0.151 Uiso 1 1 calc R U . . .
B1 B 0.1019(6) 0.6922(7) 0.0568(5) 0.074(2) Uani 1 1 d . . . . .
C26 C 0.3944(5) 0.3842(6) 0.1945(4) 0.113(3) Uani 1 1 d . . . . .
H26A H 0.4276 0.3368 0.2345 0.169 Uiso 1 1 calc R U . . .
H26B H 0.4212 0.3810 0.1424 0.169 Uiso 1 1 calc R U . . .
H26C H 0.3325 0.3598 0.1863 0.169 Uiso 1 1 calc R U . . .
C27 C 0.3975(6) 0.5004(7) 0.2260(5) 0.086(2) Uani 1 1 d . . . . .
C28 C 0.3430(6) 0.5774(8) 0.1843(5) 0.092(2) Uani 1 1 d . . . . .
H28 H 0.3050 0.5567 0.1376 0.110 Uiso 1 1 calc R U . . .
C29 C 0.3445(5) 0.6839(8) 0.2113(5) 0.094(2) Uani 1 1 d . . . . .
H29 H 0.3074 0.7356 0.1817 0.113 Uiso 1 1 calc R U . . .
C30 C 0.3974(6) 0.7186(7) 0.2789(6) 0.101(3) Uani 1 1 d . . . . .
H30 H 0.3964 0.7920 0.2972 0.121 Uiso 1 1 calc R U . . .
C31 C 0.4519(6) 0.6417(9) 0.3190(5) 0.105(3) Uani 1 1 d . . . . .
H31 H 0.4909 0.6630 0.3650 0.125 Uiso 1 1 calc R U . . .
C32 C 0.4511(5) 0.5341(8) 0.2937(5) 0.098(3) Uani 1 1 d . . . . .
H32 H 0.4882 0.4826 0.3235 0.118 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 1.415(8) . ?
F2 B1 1.378(9) . ?
O1 C17 1.230(7) . ?
O2 C12 1.200(7) . ?
O3 C12 1.366(7) . ?
O3 C13 1.455(7) . ?
N1 C1 1.353(7) . ?
N1 C4 1.406(7) . ?
N1 B1 1.567(9) . ?
N2 C9 1.382(8) . ?
N2 C6 1.413(7) . ?
N2 B1 1.514(9) . ?
N3 C16 1.373(8) . ?
N3 C17 1.401(8) . ?
N3 C18 1.481(7) . ?
N4 C23 1.364(7) . ?
N4 C25 1.463(7) . ?
N4 C24 1.472(7) . ?
C1 C22 1.392(9) . ?
C1 C2 1.460(8) . ?
C2 C3 1.392(8) . ?
C2 C17 1.445(9) . ?
C3 C15 1.408(8) . ?
C3 C4 1.451(9) . ?
C4 C5 1.357(8) . ?
C5 C6 1.426(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(8) . ?
C7 C8 1.403(8) . ?
C7 C11 1.486(8) . ?
C8 C9 1.404(8) . ?
C8 C12 1.486(9) . ?
C9 C10 1.500(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.471(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.342(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.535(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.509(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.545(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.380(8) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.516(9) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.377(9) . ?
C27 C28 1.390(9) . ?
C28 C29 1.381(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.374(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(9) . ?
C31 H31 0.9500 . ?
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
C12 O3 C13 115.0(5) . . ?
C1 N1 C4 109.7(6) . . ?
C1 N1 B1 126.2(7) . . ?
C4 N1 B1 124.0(6) . . ?
C9 N2 C6 106.0(6) . . ?
C9 N2 B1 126.0(6) . . ?
C6 N2 B1 128.0(7) . . ?
C16 N3 C17 125.2(7) . . ?
C16 N3 C18 116.5(7) . . ?
C17 N3 C18 118.3(6) . . ?
C23 N4 C25 122.0(6) . . ?
C23 N4 C24 120.9(6) . . ?
C25 N4 C24 117.0(6) . . ?
N1 C1 C22 119.9(7) . . ?
N1 C1 C2 108.2(6) . . ?
C22 C1 C2 131.8(8) . . ?
C3 C2 C17 120.0(7) . . ?
C3 C2 C1 107.6(7) . . ?
C17 C2 C1 132.4(7) . . ?
C2 C3 C15 123.7(7) . . ?
C2 C3 C4 106.8(7) . . ?
C15 C3 C4 129.5(7) . . ?
C5 C4 N1 121.4(7) . . ?
C5 C4 C3 131.0(7) . . ?
N1 C4 C3 107.6(7) . . ?
C4 C5 C6 122.7(7) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C7 C6 N2 111.3(7) . . ?
C7 C6 C5 131.7(7) . . ?
N2 C6 C5 117.0(7) . . ?
C6 C7 C8 105.0(7) . . ?
C6 C7 C11 125.1(7) . . ?
C8 C7 C11 129.9(7) . . ?
C7 C8 C9 109.7(7) . . ?
C7 C8 C12 129.3(8) . . ?
C9 C8 C12 121.0(7) . . ?
N2 C9 C8 108.1(6) . . ?
N2 C9 C10 121.2(7) . . ?
C8 C9 C10 130.7(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 122.5(7) . . ?
O2 C12 C8 127.3(8) . . ?
O3 C12 C8 110.2(7) . . ?
O3 C13 C14 106.2(6) . . ?
O3 C13 H13A 110.5 . . ?
C14 C13 H13A 110.5 . . ?
O3 C13 H13B 110.5 . . ?
C14 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C3 115.9(7) . . ?
C16 C15 H15 122.1 . . ?
C3 C15 H15 122.1 . . ?
C15 C16 N3 122.2(7) . . ?
C15 C16 H16 118.9 . . ?
N3 C16 H16 118.9 . . ?
O1 C17 N3 118.6(7) . . ?
O1 C17 C2 128.2(8) . . ?
N3 C17 C2 113.1(7) . . ?
N3 C18 C19 110.2(5) . . ?
N3 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
N3 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 111.4(6) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 111.3(6) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C1 126.4(7) . . ?
C23 C22 H22 116.8 . . ?
C1 C22 H22 116.8 . . ?
N4 C23 C22 124.5(7) . . ?
N4 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 H25A 109.5 . . ?
N4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F2 B1 F1 108.4(6) . . ?
F2 B1 N2 112.9(7) . . ?
F1 B1 N2 109.8(6) . . ?
F2 B1 N1 110.7(6) . . ?
F1 B1 N1 108.2(6) . . ?
N2 B1 N1 106.7(6) . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 118.0(8) . . ?
C32 C27 C26 123.7(9) . . ?
C28 C27 C26 118.3(9) . . ?
C29 C28 C27 119.7(8) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 122.9(8) . . ?
C30 C29 H29 118.5 . . ?
C28 C29 H29 118.5 . . ?
C29 C30 C31 116.8(8) . . ?
C29 C30 H30 121.6 . . ?
C31 C30 H30 121.6 . . ?
C30 C31 C32 121.4(8) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C27 C32 C31 121.1(8) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
 
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
C4 N1 C1 C22 179.0(5) . . . . ?
B1 N1 C1 C22 1.6(9) . . . . ?
C4 N1 C1 C2 -0.8(7) . . . . ?
B1 N1 C1 C2 -178.2(6) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
C22 C1 C2 C3 179.3(6) . . . . ?
N1 C1 C2 C17 -178.7(6) . . . . ?
C22 C1 C2 C17 1.5(12) . . . . ?
C17 C2 C3 C15 -1.6(9) . . . . ?
C1 C2 C3 C15 -179.7(6) . . . . ?
C17 C2 C3 C4 -179.7(5) . . . . ?
C1 C2 C3 C4 2.1(7) . . . . ?
C1 N1 C4 C5 -178.7(6) . . . . ?
B1 N1 C4 C5 -1.2(9) . . . . ?
C1 N1 C4 C3 2.1(7) . . . . ?
B1 N1 C4 C3 179.6(6) . . . . ?
C2 C3 C4 C5 178.2(6) . . . . ?
C15 C3 C4 C5 0.2(11) . . . . ?
C2 C3 C4 N1 -2.6(7) . . . . ?
C15 C3 C4 N1 179.3(6) . . . . ?
N1 C4 C5 C6 3.0(9) . . . . ?
C3 C4 C5 C6 -178.0(6) . . . . ?
C9 N2 C6 C7 -0.4(7) . . . . ?
B1 N2 C6 C7 -177.3(6) . . . . ?
C9 N2 C6 C5 -178.8(5) . . . . ?
B1 N2 C6 C5 4.3(9) . . . . ?
C4 C5 C6 C7 177.7(6) . . . . ?
C4 C5 C6 N2 -4.3(9) . . . . ?
N2 C6 C7 C8 0.6(7) . . . . ?
C5 C6 C7 C8 178.6(6) . . . . ?
N2 C6 C7 C11 -178.8(5) . . . . ?
C5 C6 C7 C11 -0.7(11) . . . . ?
C6 C7 C8 C9 -0.5(7) . . . . ?
C11 C7 C8 C9 178.8(6) . . . . ?
C6 C7 C8 C12 178.3(6) . . . . ?
C11 C7 C8 C12 -2.4(11) . . . . ?
C6 N2 C9 C8 0.1(6) . . . . ?
B1 N2 C9 C8 177.1(6) . . . . ?
C6 N2 C9 C10 -178.5(5) . . . . ?
B1 N2 C9 C10 -1.6(9) . . . . ?
C7 C8 C9 N2 0.2(7) . . . . ?
C12 C8 C9 N2 -178.7(5) . . . . ?
C7 C8 C9 C10 178.7(6) . . . . ?
C12 C8 C9 C10 -0.2(10) . . . . ?
C13 O3 C12 O2 1.0(9) . . . . ?
C13 O3 C12 C8 -178.6(5) . . . . ?
C7 C8 C12 O2 169.2(7) . . . . ?
C9 C8 C12 O2 -12.1(10) . . . . ?
C7 C8 C12 O3 -11.2(9) . . . . ?
C9 C8 C12 O3 167.5(6) . . . . ?
C12 O3 C13 C14 175.5(6) . . . . ?
C2 C3 C15 C16 2.1(9) . . . . ?
C4 C3 C15 C16 179.9(6) . . . . ?
C3 C15 C16 N3 -1.4(9) . . . . ?
C17 N3 C16 C15 0.1(10) . . . . ?
C18 N3 C16 C15 -177.2(6) . . . . ?
C16 N3 C17 O1 -176.4(6) . . . . ?
C18 N3 C17 O1 0.9(9) . . . . ?
C16 N3 C17 C2 0.5(9) . . . . ?
C18 N3 C17 C2 177.8(5) . . . . ?
C3 C2 C17 O1 176.7(7) . . . . ?
C1 C2 C17 O1 -5.7(12) . . . . ?
C3 C2 C17 N3 0.2(9) . . . . ?
C1 C2 C17 N3 177.8(6) . . . . ?
C16 N3 C18 C19 86.0(7) . . . . ?
C17 N3 C18 C19 -91.5(7) . . . . ?
N3 C18 C19 C20 179.8(5) . . . . ?
C18 C19 C20 C21 179.2(5) . . . . ?
N1 C1 C22 C23 -176.7(6) . . . . ?
C2 C1 C22 C23 3.0(11) . . . . ?
C25 N4 C23 C22 2.6(9) . . . . ?
C24 N4 C23 C22 178.0(6) . . . . ?
C1 C22 C23 N4 178.3(6) . . . . ?
C9 N2 B1 F2 -57.0(9) . . . . ?
C6 N2 B1 F2 119.3(7) . . . . ?
C9 N2 B1 F1 64.0(9) . . . . ?
C6 N2 B1 F1 -119.7(6) . . . . ?
C9 N2 B1 N1 -178.8(5) . . . . ?
C6 N2 B1 N1 -2.5(9) . . . . ?
C1 N1 B1 F2 54.7(9) . . . . ?
C4 N1 B1 F2 -122.3(6) . . . . ?
C1 N1 B1 F1 -63.9(8) . . . . ?
C4 N1 B1 F1 119.0(6) . . . . ?
C1 N1 B1 N2 177.9(6) . . . . ?
C4 N1 B1 N2 0.8(9) . . . . ?
C32 C27 C28 C29 0.4(10) . . . . ?
C26 C27 C28 C29 -179.7(6) . . . . ?
C27 C28 C29 C30 -0.7(11) . . . . ?
C28 C29 C30 C31 1.5(10) . . . . ?
C29 C30 C31 C32 -2.0(11) . . . . ?
C28 C27 C32 C31 -0.9(11) . . . . ?
C26 C27 C32 C31 179.2(6) . . . . ?
C30 C31 C32 C27 1.8(11) . . . . ?
 
_refine_diff_density_max    0.244
_refine_diff_density_min   -0.263
_refine_diff_density_rms    0.060



