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

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

data_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1533939'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-03-17 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          'not measured'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 B F2 N2 O2'
_chemical_formula_weight         306.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0015 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.382(4)
_cell_length_b                   13.964(5)
_cell_length_c                   27.457(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.853(7)
_cell_angle_gamma                90
_cell_volume                     4362(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20846
_cell_measurement_theta_min      1.461
_cell_measurement_theta_max      27.030

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.1150
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6999
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL02B1'
_diffrn_measurement_device_type  'Rigaku Mercury CCD2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20846
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.461
_diffrn_reflns_theta_max         27.030
_diffrn_reflns_theta_full        24.831
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4937
_reflns_number_gt                2773
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1734P)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         4937
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2874
_refine_ls_wR_factor_gt          0.2446
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.4627(4) 0.2480(4) 0.62326(15) 0.0529(12) Uani 1 1 d . . . . .
H1 H 0.3814 0.2710 0.6232 0.079 Uiso 1 1 calc R U . . .
H1A H 0.5085 0.2793 0.6496 0.079 Uiso 1 1 calc R U . . .
H1B H 0.4638 0.1785 0.6283 0.079 Uiso 1 1 calc R U . . .
C2 C 0.5150(3) 0.2709(3) 0.57567(15) 0.0433(10) Uani 1 1 d . . . . .
C3 C 0.5467(3) 0.3582(3) 0.55708(15) 0.0456(11) Uani 1 1 d . . . . .
H3 H 0.5414 0.4182 0.5732 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5881(3) 0.3432(3) 0.51021(14) 0.0388(9) Uani 1 1 d . . . . .
C5 C 0.6294(4) 0.4206(3) 0.47663(17) 0.0503(11) Uani 1 1 d . . . . .
H5 H 0.6289 0.4824 0.4936 0.075 Uiso 1 1 calc R U . . .
H5A H 0.5767 0.4238 0.4477 0.075 Uiso 1 1 calc R U . . .
H5B H 0.7093 0.4062 0.4667 0.075 Uiso 1 1 calc R U . . .
C6 C 0.5830(3) 0.2450(3) 0.50222(13) 0.0346(9) Uani 1 1 d . . . . .
C7 C 0.6128(3) 0.1880(3) 0.46174(13) 0.0330(8) Uani 1 1 d . . . . .
C8 C 0.6553(3) 0.2224(3) 0.41874(12) 0.0327(8) Uani 1 1 d . . . . .
H8 H 0.6652 0.2893 0.4142 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6832(3) 0.1597(3) 0.38248(12) 0.0306(8) Uani 1 1 d . . . . .
C10 C 0.7318(3) 0.1865(3) 0.33723(12) 0.0309(8) Uani 1 1 d . . . . .
C11 C 0.7728(3) 0.2720(3) 0.31891(14) 0.0356(9) Uani 1 1 d . . . . .
C12 C 0.7713(4) 0.3693(3) 0.34350(15) 0.0438(10) Uani 1 1 d . . . . .
H12 H 0.8083 0.4167 0.3226 0.066 Uiso 1 1 calc R U . . .
H12A H 0.8148 0.3658 0.3748 0.066 Uiso 1 1 calc R U . . .
H12B H 0.6899 0.3882 0.3489 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8174(3) 0.2525(3) 0.27408(14) 0.0418(10) Uani 1 1 d . . . . .
H13 H 0.8519 0.2981 0.2532 0.050 Uiso 1 1 calc R U . . .
C14 C 0.8042(3) 0.1571(3) 0.26437(13) 0.0356(9) Uani 1 1 d . . . . .
C15 C 0.8387(4) 0.0969(3) 0.22241(14) 0.0438(10) Uani 1 1 d . . . . .
H15 H 0.8022 0.0336 0.2248 0.066 Uiso 1 1 calc R U . . .
H15A H 0.9244 0.0899 0.2229 0.066 Uiso 1 1 calc R U . . .
H15B H 0.8122 0.1276 0.1919 0.066 Uiso 1 1 calc R U . . .
C16 C 0.3090(4) 0.1605(4) 0.45306(14) 0.0607(15) Uani 1 1 d . . . . .
H16 H 0.2230 0.1560 0.4519 0.091 Uiso 1 1 calc R U . . .
H16A H 0.3346 0.1997 0.4811 0.091 Uiso 1 1 calc R U . . .
H16B H 0.3429 0.0963 0.4563 0.091 Uiso 1 1 calc R U . . .
C17 C 0.3490(3) 0.2056(4) 0.40745(14) 0.0460(11) Uani 1 1 d . . . . .
C18 C 0.3537(3) 0.2998(3) 0.39294(14) 0.0455(11) Uani 1 1 d . . . . .
H18 H 0.3309 0.3535 0.4117 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3976(3) 0.3032(3) 0.34597(13) 0.0378(9) Uani 1 1 d . . . . .
C20 C 0.4186(3) 0.2104(3) 0.33250(12) 0.0304(8) Uani 1 1 d . . . . .
C21 C 0.4619(3) 0.1673(2) 0.28969(11) 0.0263(7) Uani 1 1 d . . . . .
C22 C 0.5000 0.2173(3) 0.2500 0.0284(10) Uani 1 2 d S T P . .
H22 H 0.5000 0.2853 0.2500 0.034 Uiso 1 2 calc R U P . .
C23 C 0.4101(4) 0.3918(3) 0.31715(15) 0.0463(10) Uani 1 1 d . . . . .
H23 H 0.4922 0.3992 0.3081 0.069 Uiso 1 1 calc R U . . .
H23A H 0.3867 0.4470 0.3366 0.069 Uiso 1 1 calc R U . . .
H23B H 0.3597 0.3879 0.2876 0.069 Uiso 1 1 calc R U . . .
N1 N 0.5398(3) 0.2049(3) 0.54312(11) 0.0390(8) Uani 1 1 d . . . . .
H1C H 0.5296 0.1430 0.5473 0.047 Uiso 1 1 calc R U . . .
N2 N 0.7537(3) 0.1173(2) 0.30343(11) 0.0339(7) Uani 1 1 d . . . . .
H2 H 0.7373 0.0561 0.3066 0.041 Uiso 1 1 calc R U . . .
N3 N 0.3887(3) 0.1527(2) 0.37063(10) 0.0357(7) Uani 1 1 d . . . . .
H3A H 0.3946 0.0898 0.3709 0.043 Uiso 1 1 calc R U . . .
F1 F 0.6834(2) -0.04697(16) 0.44811(8) 0.0449(6) Uani 1 1 d . . . . .
F2 F 0.5033(2) -0.01371(17) 0.41650(8) 0.0452(6) Uani 1 1 d . . . . .
F3 F 0.5925(2) -0.04168(16) 0.26668(8) 0.0465(6) Uani 1 1 d . . . . .
B1 B 0.6132(4) 0.0243(3) 0.43031(16) 0.0371(10) Uani 1 1 d . . . . .
B2 B 0.5000 0.0159(4) 0.2500 0.0380(14) Uani 1 2 d S T P . .
O1 O 0.6661(2) 0.06654(18) 0.38683(9) 0.0378(7) Uani 1 1 d . . . . .
O2 O 0.5961(2) 0.09513(19) 0.46841(9) 0.0378(6) Uani 1 1 d . . . . .
O3 O 0.4610(2) 0.07269(18) 0.29072(9) 0.0368(6) 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 C2 1.488(6) . ?
C2 N1 1.321(5) . ?
C2 C3 1.375(7) . ?
C3 C4 1.401(6) . ?
C4 C6 1.391(6) . ?
C4 C5 1.505(6) . ?
C6 N1 1.361(5) . ?
C6 C7 1.417(5) . ?
C7 O2 1.325(5) . ?
C7 C8 1.376(5) . ?
C8 C9 1.370(5) . ?
C9 O1 1.321(4) . ?
C9 C10 1.426(5) . ?
C10 N2 1.369(5) . ?
C10 C11 1.382(5) . ?
C11 C13 1.374(5) . ?
C11 C12 1.518(5) . ?
C13 C14 1.365(6) . ?
C14 N2 1.353(4) . ?
C14 C15 1.489(5) . ?
C16 C17 1.486(6) . ?
C17 N3 1.342(5) . ?
C17 C18 1.376(7) . ?
C18 C19 1.399(5) . ?
C19 C20 1.371(5) . ?
C19 C23 1.477(6) . ?
C20 N3 1.373(5) . ?
C20 C21 1.423(5) . ?
C21 O3 1.321(4) . ?
C21 C22 1.376(4) . ?
C22 C21 1.376(4) 2_655 ?
F1 B1 1.357(5) . ?
F2 B1 1.400(5) . ?
F3 B2 1.391(4) . ?
B1 O2 1.457(5) . ?
B1 O1 1.477(5) . ?
B2 F3 1.391(4) 2_655 ?
B2 O3 1.452(4) 2_655 ?
B2 O3 1.452(4) . ?

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 C2 C3 107.7(4) . . ?
N1 C2 C1 123.0(4) . . ?
C3 C2 C1 129.4(4) . . ?
C2 C3 C4 108.0(4) . . ?
C6 C4 C3 106.2(4) . . ?
C6 C4 C5 128.6(4) . . ?
C3 C4 C5 125.2(4) . . ?
N1 C6 C4 106.9(3) . . ?
N1 C6 C7 121.2(4) . . ?
C4 C6 C7 131.9(4) . . ?
O2 C7 C8 121.0(3) . . ?
O2 C7 C6 113.7(3) . . ?
C8 C7 C6 125.3(4) . . ?
C9 C8 C7 119.8(4) . . ?
O1 C9 C8 121.6(3) . . ?
O1 C9 C10 113.6(3) . . ?
C8 C9 C10 124.8(3) . . ?
N2 C10 C11 107.0(3) . . ?
N2 C10 C9 119.3(3) . . ?
C11 C10 C9 133.5(4) . . ?
C13 C11 C10 107.1(4) . . ?
C13 C11 C12 125.9(4) . . ?
C10 C11 C12 127.0(4) . . ?
C14 C13 C11 109.1(3) . . ?
N2 C14 C13 107.0(3) . . ?
N2 C14 C15 120.7(4) . . ?
C13 C14 C15 132.2(4) . . ?
N3 C17 C18 106.9(4) . . ?
N3 C17 C16 121.5(5) . . ?
C18 C17 C16 131.6(4) . . ?
C17 C18 C19 108.5(4) . . ?
C20 C19 C18 106.7(4) . . ?
C20 C19 C23 128.7(3) . . ?
C18 C19 C23 124.5(4) . . ?
C19 C20 N3 107.4(3) . . ?
C19 C20 C21 133.8(3) . . ?
N3 C20 C21 118.8(3) . . ?
O3 C21 C22 121.8(3) . . ?
O3 C21 C20 113.8(3) . . ?
C22 C21 C20 124.4(3) . . ?
C21 C22 C21 119.0(4) 2_655 . ?
C2 N1 C6 111.2(4) . . ?
C14 N2 C10 109.8(3) . . ?
C17 N3 C20 110.4(4) . . ?
F1 B1 F2 109.3(3) . . ?
F1 B1 O2 109.3(3) . . ?
F2 B1 O2 108.2(3) . . ?
F1 B1 O1 109.5(3) . . ?
F2 B1 O1 108.5(3) . . ?
O2 B1 O1 112.1(3) . . ?
F3 B2 F3 109.4(4) 2_655 . ?
F3 B2 O3 108.02(13) 2_655 2_655 ?
F3 B2 O3 108.80(14) . 2_655 ?
F3 B2 O3 108.79(14) 2_655 . ?
F3 B2 O3 108.02(13) . . ?
O3 B2 O3 113.8(4) 2_655 . ?
C9 O1 B1 122.1(3) . . ?
C7 O2 B1 122.9(3) . . ?
C21 O3 B2 121.8(3) . . ?

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
N1 C2 C3 C4 2.4(4) . . . . ?
C1 C2 C3 C4 -178.0(4) . . . . ?
C2 C3 C4 C6 -1.5(4) . . . . ?
C2 C3 C4 C5 178.6(4) . . . . ?
C3 C4 C6 N1 0.1(4) . . . . ?
C5 C4 C6 N1 180.0(4) . . . . ?
C3 C4 C6 C7 179.8(4) . . . . ?
C5 C4 C6 C7 -0.4(7) . . . . ?
N1 C6 C7 O2 -1.0(5) . . . . ?
C4 C6 C7 O2 179.4(4) . . . . ?
N1 C6 C7 C8 179.0(3) . . . . ?
C4 C6 C7 C8 -0.6(6) . . . . ?
O2 C7 C8 C9 -1.3(5) . . . . ?
C6 C7 C8 C9 178.7(3) . . . . ?
C7 C8 C9 O1 2.7(5) . . . . ?
C7 C8 C9 C10 -177.6(3) . . . . ?
O1 C9 C10 N2 1.1(5) . . . . ?
C8 C9 C10 N2 -178.7(3) . . . . ?
O1 C9 C10 C11 -173.4(4) . . . . ?
C8 C9 C10 C11 6.9(6) . . . . ?
N2 C10 C11 C13 0.7(4) . . . . ?
C9 C10 C11 C13 175.6(4) . . . . ?
N2 C10 C11 C12 -178.4(3) . . . . ?
C9 C10 C11 C12 -3.5(7) . . . . ?
C10 C11 C13 C14 0.3(4) . . . . ?
C12 C11 C13 C14 179.4(4) . . . . ?
C11 C13 C14 N2 -1.2(4) . . . . ?
C11 C13 C14 C15 -178.3(4) . . . . ?
N3 C17 C18 C19 0.0(4) . . . . ?
C16 C17 C18 C19 -179.2(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C17 C18 C19 C23 177.0(4) . . . . ?
C18 C19 C20 N3 -0.3(4) . . . . ?
C23 C19 C20 N3 -176.9(4) . . . . ?
C18 C19 C20 C21 179.4(4) . . . . ?
C23 C19 C20 C21 2.8(7) . . . . ?
C19 C20 C21 O3 -175.6(4) . . . . ?
N3 C20 C21 O3 4.1(4) . . . . ?
C19 C20 C21 C22 3.5(6) . . . . ?
N3 C20 C21 C22 -176.8(3) . . . . ?
O3 C21 C22 C21 0.1(2) . . . 2_655 ?
C20 C21 C22 C21 -179.0(4) . . . 2_655 ?
C3 C2 N1 C6 -2.4(4) . . . . ?
C1 C2 N1 C6 178.0(3) . . . . ?
C4 C6 N1 C2 1.4(4) . . . . ?
C7 C6 N1 C2 -178.3(3) . . . . ?
C13 C14 N2 C10 1.6(4) . . . . ?
C15 C14 N2 C10 179.2(3) . . . . ?
C11 C10 N2 C14 -1.4(4) . . . . ?
C9 C10 N2 C14 -177.2(3) . . . . ?
C18 C17 N3 C20 -0.2(4) . . . . ?
C16 C17 N3 C20 179.1(3) . . . . ?
C19 C20 N3 C17 0.3(4) . . . . ?
C21 C20 N3 C17 -179.5(3) . . . . ?
C8 C9 O1 B1 1.6(5) . . . . ?
C10 C9 O1 B1 -178.1(3) . . . . ?
F1 B1 O1 C9 -127.9(4) . . . . ?
F2 B1 O1 C9 112.9(4) . . . . ?
O2 B1 O1 C9 -6.5(5) . . . . ?
C8 C7 O2 B1 -4.4(5) . . . . ?
C6 C7 O2 B1 175.6(3) . . . . ?
F1 B1 O2 C7 129.4(3) . . . . ?
F2 B1 O2 C7 -111.7(4) . . . . ?
O1 B1 O2 C7 7.9(5) . . . . ?
C22 C21 O3 B2 -0.2(4) . . . . ?
C20 C21 O3 B2 179.0(2) . . . . ?
F3 B2 O3 C21 -120.4(4) 2_655 . . . ?
F3 B2 O3 C21 121.0(4) . . . . ?
O3 B2 O3 C21 0.1(2) 2_655 . . . ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_60206m
_database_code_depnum_ccdc_archive 'CCDC 1533940'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-03-17 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         'C27 H25 B F2 N2 O2'
_chemical_formula_sum            'C27 H25 B F2 N2 O2'
_chemical_formula_weight         458.30

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

_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'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   8.1530(19)
_cell_length_b                   17.336(3)
_cell_length_c                   17.063(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.3167(10)
_cell_angle_gamma                90
_cell_volume                     2346.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2394
_cell_measurement_theta_min      25.300
_cell_measurement_theta_max      68.200

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   0.913
_exptl_transmission_factor_max   0.956
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.756
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30070
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         7.187
_diffrn_reflns_theta_max         68.546
_diffrn_reflns_theta_full        67.687
_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             4301
_reflns_number_gt                3844
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0454P)²+0.6760P] 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         4301
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.47603(8) 0.73436(4) 0.35770(4) 0.02276(16) Uani 1 1 d . . . . .
F2 F 0.32244(8) 0.76189(4) 0.23196(4) 0.02538(16) Uani 1 1 d . . . . .
O1 O 0.24056(10) 0.66043(4) 0.30408(5) 0.02370(19) Uani 1 1 d . . . . .
O2 O 0.49362(9) 0.65342(4) 0.25054(5) 0.02153(18) Uani 1 1 d . . . . .
N1 N 0.70880(11) 0.58239(5) 0.17909(5) 0.0199(2) Uani 1 1 d . . . . .
H1 H 0.7395 0.6290 0.1971 0.024 Uiso 1 1 calc R U . . .
N2 N -0.00853(11) 0.60225(5) 0.36085(5) 0.0185(2) Uani 1 1 d . . . . .
H2 H -0.0005 0.6529 0.3617 0.022 Uiso 1 1 calc R U . . .
C7 C 0.46417(13) 0.57899(6) 0.23734(6) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.09595(13) 0.55326(6) 0.33101(6) 0.0185(2) Uani 1 1 d . . . . .
C9 C 0.22882(14) 0.58445(6) 0.29976(6) 0.0190(2) Uani 1 1 d . . . . .
C10 C -0.12431(13) 0.56181(6) 0.38842(6) 0.0189(2) Uani 1 1 d . . . . .
C11 C 0.33801(14) 0.54192(6) 0.26499(7) 0.0210(2) Uani 1 1 d . . . . .
H3 H 0.3261 0.4875 0.2602 0.025 Uiso 1 1 calc R U . . .
C12 C 0.57163(13) 0.54275(6) 0.19333(6) 0.0191(2) Uani 1 1 d . . . . .
C13 C -0.09893(14) 0.48334(6) 0.37492(6) 0.0194(2) Uani 1 1 d . . . . .
C14 C 0.78900(14) 0.53937(7) 0.13351(7) 0.0211(2) Uani 1 1 d . . . . .
C15 C 0.63708(14) 0.38477(7) -0.00599(7) 0.0226(2) Uani 1 1 d . . . . .
H4 H 0.5338 0.4116 -0.0245 0.027 Uiso 1 1 calc R U . . .
C16 C 0.56310(14) 0.47185(6) 0.15309(7) 0.0200(2) Uani 1 1 d . . . . .
C17 C -0.37754(17) 0.30687(7) 0.34262(8) 0.0320(3) Uani 1 1 d . . . . .
H5 H -0.4189 0.2705 0.3011 0.038 Uiso 1 1 calc R U . . .
C18 C -0.25798(15) 0.41375(7) 0.46303(7) 0.0248(3) Uani 1 1 d . . . . .
H6 H -0.2183 0.4504 0.5045 0.030 Uiso 1 1 calc R U . . .
C19 C -0.20862(14) 0.41972(6) 0.39025(7) 0.0216(2) Uani 1 1 d . . . . .
C20 C 0.93734(16) 0.30540(8) 0.04631(8) 0.0333(3) Uani 1 1 d . . . . .
H7 H 1.0404 0.2783 0.0644 0.040 Uiso 1 1 calc R U . . .
C21 C 0.74523(14) 0.40641(6) 0.06628(7) 0.0217(2) Uani 1 1 d . . . . .
C22 C 0.89662(16) 0.36605(8) 0.09149(8) 0.0308(3) Uani 1 1 d . . . . .
H8 H 0.9728 0.3803 0.1403 0.037 Uiso 1 1 calc R U . . .
C23 C 0.67845(15) 0.32442(7) -0.05129(7) 0.0246(2) Uani 1 1 d . . . . .
H9 H 0.6037 0.3105 -0.1007 0.030 Uiso 1 1 calc R U . . .
C24 C 0.04198(14) 0.47758(6) 0.34028(6) 0.0197(2) Uani 1 1 d . . . . .
C25 C 0.70098(14) 0.47006(6) 0.11588(6) 0.0205(2) Uani 1 1 d . . . . .
C26 C -0.27005(16) 0.36528(7) 0.33021(7) 0.0272(3) Uani 1 1 d . . . . .
H10 H -0.2377 0.3683 0.2802 0.033 Uiso 1 1 calc R U . . .
C27 C -0.36490(16) 0.35463(7) 0.47559(8) 0.0304(3) Uani 1 1 d . . . . .
H11 H -0.3967 0.3509 0.5256 0.037 Uiso 1 1 calc R U . . .
B1 B 0.38322(16) 0.70293(7) 0.28604(8) 0.0202(3) Uani 1 1 d . . . . .
C29 C 0.82754(16) 0.28446(7) -0.02504(7) 0.0276(3) Uani 1 1 d . . . . .
H12 H 0.8546 0.2427 -0.0559 0.033 Uiso 1 1 calc R U . . .
C30 C -0.42491(16) 0.30142(7) 0.41553(8) 0.0325(3) Uani 1 1 d . . . . .
H13 H -0.4982 0.2613 0.4241 0.039 Uiso 1 1 calc R U . . .
C33 C -0.24803(14) 0.60073(7) 0.42725(7) 0.0241(2) Uani 1 1 d . . . . .
H14 H -0.2033 0.6022 0.4857 0.036 Uiso 1 1 calc R U . . .
H15 H -0.3545 0.5721 0.4150 0.036 Uiso 1 1 calc R U . . .
H16 H -0.2676 0.6535 0.4065 0.036 Uiso 1 1 calc R U . . .
C35 C 0.43054(15) 0.41086(7) 0.14630(7) 0.0260(3) Uani 1 1 d . . . . .
H17 H 0.4332 0.3895 0.1998 0.039 Uiso 1 1 calc R U . . .
H18 H 0.4522 0.3696 0.1107 0.039 Uiso 1 1 calc R U . . .
H19 H 0.3195 0.4335 0.1240 0.039 Uiso 1 1 calc R U . . .
C34 C 0.93922(15) 0.56899(8) 0.10708(8) 0.0297(3) Uani 1 1 d . . . . .
H20 H 0.9616 0.6223 0.1255 0.045 Uiso 1 1 calc R U . . .
H21 H 0.9175 0.5673 0.0482 0.045 Uiso 1 1 calc R U . . .
H22 H 1.0373 0.5368 0.1302 0.045 Uiso 1 1 calc R U . . .
C31 C 0.12662(16) 0.40426(6) 0.32485(7) 0.0256(3) Uani 1 1 d . . . . .
H23 H 0.1133 0.3973 0.2667 0.038 Uiso 1 1 calc R U . . .
H24 H 0.0751 0.3606 0.3467 0.038 Uiso 1 1 calc R U . . .
H25 H 0.2468 0.4069 0.3510 0.038 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3922(15) . ?
F2 B1 1.3897(14) . ?
O1 C9 1.3215(13) . ?
O1 B1 1.4682(15) . ?
O2 C7 1.3223(13) . ?
O2 B1 1.4714(14) . ?
N1 C14 1.3501(14) . ?
N1 C12 1.3810(14) . ?
N1 H1 0.8800 . ?
N2 C10 1.3447(14) . ?
N2 C8 1.3806(14) . ?
N2 H2 0.8800 . ?
C7 C11 1.3846(15) . ?
C7 C12 1.4245(15) . ?
C8 C24 1.4042(15) . ?
C8 C9 1.4200(15) . ?
C9 C11 1.3897(15) . ?
C10 C13 1.4030(15) . ?
C10 C33 1.4898(15) . ?
C11 H3 0.9500 . ?
C12 C16 1.4017(15) . ?
C13 C24 1.4113(16) . ?
C13 C19 1.4806(15) . ?
C14 C25 1.3963(16) . ?
C14 C34 1.4905(16) . ?
C15 C23 1.3877(16) . ?
C15 C21 1.3921(17) . ?
C15 H4 0.9500 . ?
C16 C25 1.4130(16) . ?
C16 C35 1.4973(16) . ?
C17 C26 1.3871(17) . ?
C17 C30 1.388(2) . ?
C17 H5 0.9500 . ?
C18 C27 1.3937(17) . ?
C18 C19 1.3946(17) . ?
C18 H6 0.9500 . ?
C19 C26 1.3981(17) . ?
C20 C29 1.3833(19) . ?
C20 C22 1.3885(18) . ?
C20 H7 0.9500 . ?
C21 C22 1.3977(17) . ?
C21 C25 1.4848(15) . ?
C22 H8 0.9500 . ?
C23 C29 1.3811(18) . ?
C23 H9 0.9500 . ?
C24 C31 1.4983(15) . ?
C26 H10 0.9500 . ?
C27 C30 1.3818(19) . ?
C27 H11 0.9500 . ?
C29 H12 0.9500 . ?
C30 H13 0.9500 . ?
C33 H14 0.9800 . ?
C33 H15 0.9800 . ?
C33 H16 0.9800 . ?
C35 H17 0.9800 . ?
C35 H18 0.9800 . ?
C35 H19 0.9800 . ?
C34 H20 0.9800 . ?
C34 H21 0.9800 . ?
C34 H22 0.9800 . ?
C31 H23 0.9800 . ?
C31 H24 0.9800 . ?
C31 H25 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
C9 O1 B1 122.63(9) . . ?
C7 O2 B1 122.35(9) . . ?
C14 N1 C12 110.23(9) . . ?
C14 N1 H1 124.9 . . ?
C12 N1 H1 124.9 . . ?
C10 N2 C8 110.54(9) . . ?
C10 N2 H2 124.7 . . ?
C8 N2 H2 124.7 . . ?
O2 C7 C11 120.98(10) . . ?
O2 C7 C12 114.24(9) . . ?
C11 C7 C12 124.78(10) . . ?
N2 C8 C24 107.29(9) . . ?
N2 C8 C9 119.54(10) . . ?
C24 C8 C9 133.16(10) . . ?
O1 C9 C11 120.49(10) . . ?
O1 C9 C8 114.23(9) . . ?
C11 C9 C8 125.26(10) . . ?
N2 C10 C13 107.82(9) . . ?
N2 C10 C33 121.41(10) . . ?
C13 C10 C33 130.75(10) . . ?
C7 C11 C9 119.90(10) . . ?
C7 C11 H3 120.0 . . ?
C9 C11 H3 120.0 . . ?
N1 C12 C16 107.51(9) . . ?
N1 C12 C7 119.65(10) . . ?
C16 C12 C7 132.67(10) . . ?
C10 C13 C24 107.60(9) . . ?
C10 C13 C19 125.12(10) . . ?
C24 C13 C19 127.18(10) . . ?
N1 C14 C25 107.84(9) . . ?
N1 C14 C34 121.65(10) . . ?
C25 C14 C34 130.44(10) . . ?
C23 C15 C21 120.73(11) . . ?
C23 C15 H4 119.6 . . ?
C21 C15 H4 119.6 . . ?
C12 C16 C25 106.53(10) . . ?
C12 C16 C35 127.63(10) . . ?
C25 C16 C35 125.77(10) . . ?
C26 C17 C30 120.16(12) . . ?
C26 C17 H5 119.9 . . ?
C30 C17 H5 119.9 . . ?
C27 C18 C19 120.70(11) . . ?
C27 C18 H6 119.6 . . ?
C19 C18 H6 119.6 . . ?
C18 C19 C26 118.31(10) . . ?
C18 C19 C13 121.50(10) . . ?
C26 C19 C13 120.15(10) . . ?
C29 C20 C22 119.89(12) . . ?
C29 C20 H7 120.1 . . ?
C22 C20 H7 120.1 . . ?
C15 C21 C22 118.16(10) . . ?
C15 C21 C25 121.18(10) . . ?
C22 C21 C25 120.66(10) . . ?
C20 C22 C21 121.02(12) . . ?
C20 C22 H8 119.5 . . ?
C21 C22 H8 119.5 . . ?
C29 C23 C15 120.42(11) . . ?
C29 C23 H9 119.8 . . ?
C15 C23 H9 119.8 . . ?
C8 C24 C13 106.71(9) . . ?
C8 C24 C31 127.14(10) . . ?
C13 C24 C31 125.87(10) . . ?
C14 C25 C16 107.87(10) . . ?
C14 C25 C21 125.59(10) . . ?
C16 C25 C21 126.54(10) . . ?
C17 C26 C19 120.88(11) . . ?
C17 C26 H10 119.6 . . ?
C19 C26 H10 119.6 . . ?
C30 C27 C18 120.26(12) . . ?
C30 C27 H11 119.9 . . ?
C18 C27 H11 119.9 . . ?
F2 B1 F1 109.50(9) . . ?
F2 B1 O1 109.25(9) . . ?
F1 B1 O1 107.99(9) . . ?
F2 B1 O2 108.30(9) . . ?
F1 B1 O2 109.25(9) . . ?
O1 B1 O2 112.51(9) . . ?
C23 C29 C20 119.77(11) . . ?
C23 C29 H12 120.1 . . ?
C20 C29 H12 120.1 . . ?
C27 C30 C17 119.69(11) . . ?
C27 C30 H13 120.2 . . ?
C17 C30 H13 120.2 . . ?
C10 C33 H14 109.5 . . ?
C10 C33 H15 109.5 . . ?
H14 C33 H15 109.5 . . ?
C10 C33 H16 109.5 . . ?
H14 C33 H16 109.5 . . ?
H15 C33 H16 109.5 . . ?
C16 C35 H17 109.5 . . ?
C16 C35 H18 109.5 . . ?
H17 C35 H18 109.5 . . ?
C16 C35 H19 109.5 . . ?
H17 C35 H19 109.5 . . ?
H18 C35 H19 109.5 . . ?
C14 C34 H20 109.5 . . ?
C14 C34 H21 109.5 . . ?
H20 C34 H21 109.5 . . ?
C14 C34 H22 109.5 . . ?
H20 C34 H22 109.5 . . ?
H21 C34 H22 109.5 . . ?
C24 C31 H23 109.5 . . ?
C24 C31 H24 109.5 . . ?
H23 C31 H24 109.5 . . ?
C24 C31 H25 109.5 . . ?
H23 C31 H25 109.5 . . ?
H24 C31 H25 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
B1 O2 C7 C11 -7.57(15) . . . . ?
B1 O2 C7 C12 172.34(9) . . . . ?
C10 N2 C8 C24 0.16(12) . . . . ?
C10 N2 C8 C9 -179.21(9) . . . . ?
B1 O1 C9 C11 -10.68(16) . . . . ?
B1 O1 C9 C8 170.91(10) . . . . ?
N2 C8 C9 O1 1.18(14) . . . . ?
C24 C8 C9 O1 -178.01(11) . . . . ?
N2 C8 C9 C11 -177.15(10) . . . . ?
C24 C8 C9 C11 3.7(2) . . . . ?
C8 N2 C10 C13 -1.37(12) . . . . ?
C8 N2 C10 C33 177.23(10) . . . . ?
O2 C7 C11 C9 6.78(16) . . . . ?
C12 C7 C11 C9 -173.11(10) . . . . ?
O1 C9 C11 C7 2.42(16) . . . . ?
C8 C9 C11 C7 -179.35(10) . . . . ?
C14 N1 C12 C16 -1.36(12) . . . . ?
C14 N1 C12 C7 -177.17(10) . . . . ?
O2 C7 C12 N1 9.63(15) . . . . ?
C11 C7 C12 N1 -170.47(10) . . . . ?
O2 C7 C12 C16 -164.93(11) . . . . ?
C11 C7 C12 C16 15.0(2) . . . . ?
N2 C10 C13 C24 2.03(12) . . . . ?
C33 C10 C13 C24 -176.39(11) . . . . ?
N2 C10 C13 C19 -174.60(10) . . . . ?
C33 C10 C13 C19 6.97(19) . . . . ?
C12 N1 C14 C25 1.10(12) . . . . ?
C12 N1 C14 C34 178.30(10) . . . . ?
N1 C12 C16 C25 1.07(12) . . . . ?
C7 C12 C16 C25 176.11(11) . . . . ?
N1 C12 C16 C35 -176.01(11) . . . . ?
C7 C12 C16 C35 -1.0(2) . . . . ?
C27 C18 C19 C26 0.43(17) . . . . ?
C27 C18 C19 C13 178.29(11) . . . . ?
C10 C13 C19 C18 -48.89(16) . . . . ?
C24 C13 C19 C18 135.14(12) . . . . ?
C10 C13 C19 C26 128.93(12) . . . . ?
C24 C13 C19 C26 -47.05(16) . . . . ?
C23 C15 C21 C22 0.42(17) . . . . ?
C23 C15 C21 C25 -179.00(10) . . . . ?
C29 C20 C22 C21 0.3(2) . . . . ?
C15 C21 C22 C20 -0.80(19) . . . . ?
C25 C21 C22 C20 178.63(12) . . . . ?
C21 C15 C23 C29 0.40(17) . . . . ?
N2 C8 C24 C13 1.10(12) . . . . ?
C9 C8 C24 C13 -179.64(11) . . . . ?
N2 C8 C24 C31 -173.06(10) . . . . ?
C9 C8 C24 C31 6.2(2) . . . . ?
C10 C13 C24 C8 -1.91(12) . . . . ?
C19 C13 C24 C8 174.63(10) . . . . ?
C10 C13 C24 C31 172.34(11) . . . . ?
C19 C13 C24 C31 -11.11(18) . . . . ?
N1 C14 C25 C16 -0.40(12) . . . . ?
C34 C14 C25 C16 -177.28(12) . . . . ?
N1 C14 C25 C21 179.26(10) . . . . ?
C34 C14 C25 C21 2.4(2) . . . . ?
C12 C16 C25 C14 -0.42(12) . . . . ?
C35 C16 C25 C14 176.72(11) . . . . ?
C12 C16 C25 C21 179.92(10) . . . . ?
C35 C16 C25 C21 -2.94(18) . . . . ?
C15 C21 C25 C14 -116.53(13) . . . . ?
C22 C21 C25 C14 64.06(16) . . . . ?
C15 C21 C25 C16 63.07(16) . . . . ?
C22 C21 C25 C16 -116.34(14) . . . . ?
C30 C17 C26 C19 -0.42(19) . . . . ?
C18 C19 C26 C17 0.09(17) . . . . ?
C13 C19 C26 C17 -177.79(11) . . . . ?
C19 C18 C27 C30 -0.64(19) . . . . ?
C9 O1 B1 F2 129.72(10) . . . . ?
C9 O1 B1 F1 -111.25(11) . . . . ?
C9 O1 B1 O2 9.40(15) . . . . ?
C7 O2 B1 F2 -121.04(10) . . . . ?
C7 O2 B1 F1 119.75(10) . . . . ?
C7 O2 B1 O1 -0.17(14) . . . . ?
C15 C23 C29 C20 -0.87(18) . . . . ?
C22 C20 C29 C23 0.49(19) . . . . ?
C18 C27 C30 C17 0.3(2) . . . . ?
C26 C17 C30 C27 0.2(2) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_60218m2
_database_code_depnum_ccdc_archive 'CCDC 1533941'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-03-17 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         '2(C15 H17 B F2 N2 O2), C12 H28 N, C6 H14, Cl'
_chemical_formula_sum            'C48 H76 B2 Cl F4 N5 O4'
_chemical_formula_weight         920.20

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   11.592(4)
_cell_length_b                   29.363(9)
_cell_length_c                   15.588(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.696(5)
_cell_angle_gamma                90
_cell_volume                     5132(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2332
_cell_measurement_theta_min      25.70
_cell_measurement_theta_max      67.90

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             1976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.150
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            63179
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         6.601
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_full        65.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             8887
_reflns_number_gt                4804
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.2000P)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         8887
_refine_ls_number_parameters     591
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.1070
_refine_ls_wR_factor_ref         0.3180
_refine_ls_wR_factor_gt          0.2918
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76944(13) 0.00489(5) 0.72281(9) 0.0672(4) Uani 1 1 d . . . . .
F4 F 0.9459(3) -0.19143(10) 0.50263(19) 0.0615(8) Uani 1 1 d . . . . .
O3 O 0.9651(3) -0.11391(12) 0.5156(3) 0.0652(10) Uani 1 1 d . U . . .
F5 F 0.8293(3) -0.14799(12) 0.3979(2) 0.0884(11) Uani 1 1 d . . . . .
N3 N 1.0043(4) -0.00925(14) 0.6394(3) 0.0546(11) Uani 1 1 d . . . . .
H43 H 0.9412 -0.0069 0.6609 0.066 Uiso 1 1 calc R U . . .
C5 C 0.9421(4) -0.08156(17) 0.5644(3) 0.0467(12) Uani 1 1 d . U . . .
N4 N 0.6271(3) -0.08957(15) 0.6603(3) 0.0549(11) Uani 1 1 d . . . . .
H44 H 0.6697 -0.0651 0.6792 0.066 Uiso 1 1 calc R U . . .
C7 C 1.0240(4) -0.04496(16) 0.5876(3) 0.0467(11) Uani 1 1 d . . . . .
C8 C 0.7651(4) -0.12075(17) 0.5797(3) 0.0465(12) Uani 1 1 d . . . . .
O4 O 0.7892(3) -0.15535(14) 0.5365(4) 0.0881(14) Uani 1 1 d . . . . .
C10 C 0.8379(4) -0.08362(18) 0.5937(3) 0.0525(12) Uani 1 1 d . . . . .
H45 H 0.8171 -0.0582 0.6244 0.063 Uiso 1 1 calc R U . . .
C11 C 0.6597(4) -0.12376(18) 0.6107(3) 0.0526(13) Uani 1 1 d . . . . .
C12 C 0.5197(4) -0.0992(2) 0.6760(4) 0.0667(16) Uani 1 1 d . . . . .
C13 C 1.1335(4) -0.03633(18) 0.5670(3) 0.0554(13) Uani 1 1 d . . . . .
C44 C 0.5678(4) -0.15678(19) 0.5950(4) 0.0584(14) Uani 1 1 d . . . . .
C15 C 1.0935(5) 0.02160(19) 0.6533(3) 0.0603(14) Uani 1 1 d . . . . .
C16 C 0.4828(5) -0.1405(2) 0.6363(4) 0.0691(16) Uani 1 1 d . . . . .
H46 H 0.4104 -0.1554 0.6370 0.083 Uiso 1 1 calc R U . . .
C17 C 1.1751(5) 0.0046(2) 0.6088(4) 0.0663(16) Uani 1 1 d . . . . .
H47 H 1.2481 0.0189 0.6073 0.080 Uiso 1 1 calc R U . . .
C18 C 0.5593(5) -0.1995(2) 0.5405(5) 0.0766(18) Uani 1 1 d . . . . .
H1 H 0.5087 -0.2218 0.5605 0.115 Uiso 1 1 calc R U . . .
H2 H 0.6392 -0.2124 0.5475 0.115 Uiso 1 1 calc R U . . .
H3 H 0.5245 -0.1923 0.4778 0.115 Uiso 1 1 calc R U . . .
C19 C 1.1938(4) -0.0644(2) 0.5130(4) 0.0689(16) Uani 1 1 d . . . . .
H4 H 1.2530 -0.0458 0.4939 0.103 Uiso 1 1 calc R U . . .
H5 H 1.1348 -0.0758 0.4608 0.103 Uiso 1 1 calc R U . . .
H6 H 1.2336 -0.0901 0.5483 0.103 Uiso 1 1 calc R U . . .
B2 B 0.8821(6) -0.1522(2) 0.4871(5) 0.0614(17) Uani 1 1 d . . . . .
C21 C 1.0940(7) 0.0636(2) 0.7062(4) 0.0813(19) Uani 1 1 d . . . . .
H7 H 1.0120 0.0717 0.7059 0.122 Uiso 1 1 calc R U . . .
H8 H 1.1304 0.0885 0.6804 0.122 Uiso 1 1 calc R U . . .
H9 H 1.1401 0.0582 0.7674 0.122 Uiso 1 1 calc R U . . .
C22 C 0.4636(6) -0.0668(3) 0.7276(4) 0.0859(19) Uani 1 1 d . . . . .
H10 H 0.4894 -0.0743 0.7908 0.129 Uiso 1 1 calc R U . . .
H11 H 0.3766 -0.0692 0.7074 0.129 Uiso 1 1 calc R U . . .
H12 H 0.4880 -0.0356 0.7183 0.129 Uiso 1 1 calc R U . . .
O1 O 0.0068(3) 0.13133(12) 0.9742(2) 0.0551(9) Uani 1 1 d . . . . .
F2 F -0.1229(3) 0.16312(9) 1.04991(18) 0.0603(8) Uani 1 1 d . . . . .
F3 F -0.0093(3) 0.20919(11) 0.98732(19) 0.0671(8) Uani 1 1 d . . . . .
O2 O -0.1718(3) 0.17300(11) 0.8960(2) 0.0533(8) Uani 1 1 d . . . . .
N2 N 0.0128(4) 0.01813(14) 0.8867(3) 0.0536(10) Uani 1 1 d . . . . .
H48 H -0.0530 0.0149 0.8441 0.064 Uiso 1 1 calc R U . . .
C28 C -0.1480(4) 0.09487(17) 0.8719(3) 0.0472(11) Uani 1 1 d . . . . .
H49 H -0.1819 0.0674 0.8446 0.057 Uiso 1 1 calc R U . . .
N1 N -0.3596(3) 0.10291(15) 0.7276(3) 0.0535(10) Uani 1 1 d . . . . .
H50 H -0.3188 0.0779 0.7253 0.064 Uiso 1 1 calc R U . . .
C30 C -0.2123(4) 0.13523(17) 0.8537(3) 0.0456(11) Uani 1 1 d . . . . .
C31 C 0.0412(4) 0.05606(18) 0.9401(3) 0.0511(12) Uani 1 1 d . . . . .
C32 C -0.3220(4) 0.13812(17) 0.7864(3) 0.0487(12) Uani 1 1 d . . . . .
C33 C -0.0346(4) 0.09426(17) 0.9297(3) 0.0455(11) Uani 1 1 d . . . . .
C34 C 0.1012(5) -0.0136(2) 0.9093(4) 0.0654(16) Uani 1 1 d . . . . .
C35 C -0.4692(4) 0.1125(2) 0.6733(4) 0.0644(15) Uani 1 1 d . . . . .
C36 C 0.1523(4) 0.0475(2) 0.9995(3) 0.0585(14) Uani 1 1 d . . . . .
C37 C 0.1874(5) 0.0040(2) 0.9793(4) 0.0702(17) Uani 1 1 d . . . . .
H51 H 0.2590 -0.0110 1.0089 0.084 Uiso 1 1 calc R U . . .
B1 B -0.0733(6) 0.1698(2) 0.9779(4) 0.0551(15) Uani 1 1 d . . . . .
C39 C -0.4999(5) 0.1550(2) 0.6978(4) 0.0697(16) Uani 1 1 d . . . . .
H52 H -0.5720 0.1705 0.6709 0.084 Uiso 1 1 calc R U . . .
C40 C -0.4103(4) 0.17204(19) 0.7676(4) 0.0585(14) Uani 1 1 d . . . . .
C41 C -0.4108(6) 0.2165(2) 0.8137(4) 0.0771(17) Uani 1 1 d . . . . .
H13 H -0.4927 0.2279 0.8023 0.116 Uiso 1 1 calc R U . . .
H14 H -0.3617 0.2385 0.7915 0.116 Uiso 1 1 calc R U . . .
H15 H -0.3782 0.2123 0.8777 0.116 Uiso 1 1 calc R U . . .
C42 C 0.2181(5) 0.0769(2) 1.0730(4) 0.0748(17) Uani 1 1 d . . . . .
H16 H 0.2696 0.0979 1.0508 0.112 Uiso 1 1 calc R U . . .
H17 H 0.2670 0.0579 1.1201 0.112 Uiso 1 1 calc R U . . .
H18 H 0.1611 0.0944 1.0967 0.112 Uiso 1 1 calc R U . . .
C43 C -0.5278(6) 0.0803(2) 0.6038(4) 0.0835(19) Uani 1 1 d . . . . .
H19 H -0.5045 0.0871 0.5490 0.125 Uiso 1 1 calc R U . . .
H20 H -0.6145 0.0831 0.5932 0.125 Uiso 1 1 calc R U . . .
H21 H -0.5035 0.0492 0.6228 0.125 Uiso 1 1 calc R U . . .
N5 N 0.0314(3) 0.24748(13) 0.7409(2) 0.0457(9) Uani 1 1 d . . . . .
C57 C 0.5963(5) 0.1959(2) 0.0802(4) 0.0669(15) Uani 1 1 d . . . . .
H22 H 0.6745 0.2014 0.0690 0.100 Uiso 1 1 calc R U . . .
H23 H 0.5934 0.2101 0.1365 0.100 Uiso 1 1 calc R U . . .
H24 H 0.5340 0.2090 0.0320 0.100 Uiso 1 1 calc R U . . .
C45 C -0.1811(5) 0.3322(2) 0.8177(4) 0.0782(18) Uani 1 1 d . . . . .
H25 H -0.2485 0.3111 0.8090 0.117 Uiso 1 1 calc R U . . .
H26 H -0.2104 0.3626 0.7966 0.117 Uiso 1 1 calc R U . . .
H27 H -0.1403 0.3338 0.8810 0.117 Uiso 1 1 calc R U . . .
C46 C -0.2272(5) 0.1861(2) 0.5740(4) 0.0764(17) Uani 1 1 d . . . . .
H28 H -0.2646 0.2126 0.5398 0.115 Uiso 1 1 calc R U . . .
H29 H -0.2892 0.1657 0.5842 0.115 Uiso 1 1 calc R U . . .
H30 H -0.1784 0.1699 0.5409 0.115 Uiso 1 1 calc R U . . .
C47 C 0.2093(5) 0.2627(2) 0.6759(4) 0.0806(19) Uani 1 1 d . . . . .
H53 H 0.2565 0.2394 0.7158 0.097 Uiso 1 1 calc R U . . .
H54 H 0.1678 0.2471 0.6203 0.097 Uiso 1 1 calc R U . . .
C58 C 0.5653(6) 0.1193(4) -0.0051(5) 0.098(3) Uani 1 1 d . . . . .
H55 H 0.5052 0.1350 -0.0523 0.118 Uiso 1 1 calc R U . . .
H56 H 0.6428 0.1213 -0.0208 0.118 Uiso 1 1 calc R U . . .
C48 C -0.0372(5) 0.2729(2) 0.7992(4) 0.0793(18) Uani 1 1 d . . . . .
H57 H -0.0988 0.2520 0.8103 0.095 Uiso 1 1 calc R U . . .
H58 H 0.0195 0.2790 0.8573 0.095 Uiso 1 1 calc R U . . .
C49 C -0.1517(5) 0.2012(3) 0.6593(5) 0.094(2) Uani 1 1 d . . . . .
H59 H -0.1146 0.1741 0.6928 0.113 Uiso 1 1 calc R U . . .
H60 H -0.2032 0.2156 0.6934 0.113 Uiso 1 1 calc R U . . .
C63 C 0.0933(6) -0.0571(2) 0.8599(5) 0.0811(19) Uani 1 1 d . . . . .
H31 H 0.0106 -0.0678 0.8442 0.122 Uiso 1 1 calc R U . . .
H32 H 0.1443 -0.0799 0.8972 0.122 Uiso 1 1 calc R U . . .
H33 H 0.1201 -0.0523 0.8058 0.122 Uiso 1 1 calc R U . . .
C50 C 0.2924(5) 0.2969(3) 0.6551(4) 0.0853(19) Uani 1 1 d . . . . .
H34 H 0.2466 0.3209 0.6177 0.128 Uiso 1 1 calc R U . . .
H35 H 0.3452 0.2821 0.6235 0.128 Uiso 1 1 calc R U . . .
H36 H 0.3401 0.3103 0.7103 0.128 Uiso 1 1 calc R U . . .
C51 C 0.0920(5) 0.2081(2) 0.7903(4) 0.0832(19) Uani 1 1 d . . . . .
H61 H 0.0310 0.1907 0.8109 0.100 Uiso 1 1 calc R U . . .
H62 H 0.1185 0.1885 0.7474 0.100 Uiso 1 1 calc R U . . .
C52 C -0.0561(5) 0.2336(2) 0.6544(4) 0.0708(16) Uani 1 1 d . . . . .
H63 H -0.0943 0.2616 0.6250 0.085 Uiso 1 1 calc R U . . .
H64 H -0.0098 0.2202 0.6154 0.085 Uiso 1 1 calc R U . . .
C53 C 0.1179(5) 0.2815(2) 0.7184(4) 0.0782(18) Uani 1 1 d . . . . .
H65 H 0.0711 0.3047 0.6783 0.094 Uiso 1 1 calc R U . . .
H66 H 0.1598 0.2971 0.7738 0.094 Uiso 1 1 calc R U . . .
C54 C 0.1938(6) 0.2138(3) 0.8666(4) 0.102(3) Uani 1 1 d . . . . .
H67 H 0.1663 0.2294 0.9141 0.123 Uiso 1 1 calc R U . . .
H68 H 0.2524 0.2340 0.8492 0.123 Uiso 1 1 calc R U . . .
C59 C 0.5762(7) 0.1453(3) 0.0852(5) 0.107(3) Uani 1 1 d . . . . .
H69 H 0.5023 0.1402 0.1047 0.129 Uiso 1 1 calc R U . . .
H70 H 0.6432 0.1320 0.1308 0.129 Uiso 1 1 calc R U . . .
C55 C 0.2551(6) 0.1713(3) 0.9034(5) 0.097(2) Uani 1 1 d . . . . .
H37 H 0.1966 0.1495 0.9149 0.145 Uiso 1 1 calc R U . . .
H38 H 0.3145 0.1780 0.9589 0.145 Uiso 1 1 calc R U . . .
H39 H 0.2949 0.1581 0.8607 0.145 Uiso 1 1 calc R U . . .
C60 C 0.5179(7) 0.0443(4) -0.0991(7) 0.135(4) Uani 1 1 d . . . . .
H71 H 0.5855 0.0500 -0.1257 0.162 Uiso 1 1 calc R U . . .
H72 H 0.5161 0.0114 -0.0856 0.162 Uiso 1 1 calc R U . . .
C61 C 0.5348(7) 0.0754(3) -0.0043(6) 0.102(2) Uani 1 1 d . . . . .
H73 H 0.4587 0.0739 0.0134 0.122 Uiso 1 1 calc R U . . .
H74 H 0.5959 0.0601 0.0429 0.122 Uiso 1 1 calc R U . . .
C56 C -0.0961(6) 0.3159(3) 0.7670(4) 0.090(2) Uani 1 1 d . . . . .
H75 H -0.1398 0.3121 0.7040 0.108 Uiso 1 1 calc R U . . .
H76 H -0.0343 0.3395 0.7696 0.108 Uiso 1 1 calc R U . . .
C62 C 0.4091(10) 0.0574(6) -0.1590(6) 0.211(8) Uani 1 1 d . . . . .
H40 H 0.4153 0.0533 -0.2200 0.316 Uiso 1 1 calc R U . . .
H41 H 0.3930 0.0895 -0.1493 0.316 Uiso 1 1 calc R U . . .
H42 H 0.3440 0.0386 -0.1489 0.316 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
F4 B2 1.358(7) . ?
O3 C5 1.286(6) . ?
O3 B2 1.472(7) . ?
F5 B2 1.375(8) . ?
N3 C15 1.351(6) . ?
N3 C7 1.378(6) . ?
N3 H43 0.8800 . ?
C5 C10 1.396(7) . ?
C5 C7 1.419(6) . ?
N4 C12 1.358(7) . ?
N4 C11 1.378(7) . ?
N4 H44 0.8800 . ?
C7 C13 1.409(7) . ?
C8 O4 1.288(6) . ?
C8 C10 1.362(7) . ?
C8 C11 1.425(7) . ?
O4 B2 1.478(8) . ?
C10 H45 0.9500 . ?
C11 C44 1.415(7) . ?
C12 C16 1.378(9) . ?
C12 C22 1.497(9) . ?
C13 C17 1.394(8) . ?
C13 C19 1.475(8) . ?
C44 C16 1.392(8) . ?
C44 C18 1.506(9) . ?
C15 C17 1.399(8) . ?
C15 C21 1.482(8) . ?
C16 H46 0.9500 . ?
C17 H47 0.9500 . ?
C18 H1 0.9800 . ?
C18 H2 0.9800 . ?
C18 H3 0.9800 . ?
C19 H4 0.9800 . ?
C19 H5 0.9800 . ?
C19 H6 0.9800 . ?
C21 H7 0.9800 . ?
C21 H8 0.9800 . ?
C21 H9 0.9800 . ?
C22 H10 0.9800 . ?
C22 H11 0.9800 . ?
C22 H12 0.9800 . ?
O1 C33 1.314(6) . ?
O1 B1 1.474(7) . ?
F2 B1 1.400(7) . ?
F3 B1 1.360(7) . ?
O2 C30 1.315(6) . ?
O2 B1 1.484(7) . ?
N2 C34 1.363(6) . ?
N2 C31 1.380(6) . ?
N2 H48 0.8800 . ?
C28 C30 1.390(7) . ?
C28 C33 1.393(6) . ?
C28 H49 0.9500 . ?
N1 C35 1.365(6) . ?
N1 C32 1.377(6) . ?
N1 H50 0.8800 . ?
C30 C32 1.431(6) . ?
C31 C36 1.405(7) . ?
C31 C33 1.408(7) . ?
C32 C40 1.405(7) . ?
C34 C37 1.379(9) . ?
C34 C63 1.482(9) . ?
C35 C39 1.379(9) . ?
C35 C43 1.468(8) . ?
C36 C37 1.400(8) . ?
C36 C42 1.482(8) . ?
C37 H51 0.9500 . ?
C39 C40 1.392(8) . ?
C39 H52 0.9500 . ?
C40 C41 1.491(8) . ?
C41 H13 0.9800 . ?
C41 H14 0.9800 . ?
C41 H15 0.9800 . ?
C42 H16 0.9800 . ?
C42 H17 0.9800 . ?
C42 H18 0.9800 . ?
C43 H19 0.9800 . ?
C43 H20 0.9800 . ?
C43 H21 0.9800 . ?
N5 C51 1.466(7) . ?
N5 C53 1.516(7) . ?
N5 C52 1.523(7) . ?
N5 C48 1.546(7) . ?
C57 C59 1.509(10) . ?
C57 H22 0.9800 . ?
C57 H23 0.9800 . ?
C57 H24 0.9800 . ?
C45 C56 1.491(9) . ?
C45 H25 0.9800 . ?
C45 H26 0.9800 . ?
C45 H27 0.9800 . ?
C46 C49 1.463(9) . ?
C46 H28 0.9800 . ?
C46 H29 0.9800 . ?
C46 H30 0.9800 . ?
C47 C50 1.484(9) . ?
C47 C53 1.491(9) . ?
C47 H53 0.9900 . ?
C47 H54 0.9900 . ?
C58 C61 1.336(11) . ?
C58 C59 1.579(11) . ?
C58 H55 0.9900 . ?
C58 H56 0.9900 . ?
C48 C56 1.461(9) . ?
C48 H57 0.9900 . ?
C48 H58 0.9900 . ?
C49 C52 1.476(9) . ?
C49 H59 0.9900 . ?
C49 H60 0.9900 . ?
C63 H31 0.9800 . ?
C63 H32 0.9800 . ?
C63 H33 0.9800 . ?
C50 H34 0.9800 . ?
C50 H35 0.9800 . ?
C50 H36 0.9800 . ?
C51 C54 1.456(9) . ?
C51 H61 0.9900 . ?
C51 H62 0.9900 . ?
C52 H63 0.9900 . ?
C52 H64 0.9900 . ?
C53 H65 0.9900 . ?
C53 H66 0.9900 . ?
C54 C55 1.480(10) . ?
C54 H67 0.9900 . ?
C54 H68 0.9900 . ?
C59 H69 0.9900 . ?
C59 H70 0.9900 . ?
C55 H37 0.9800 . ?
C55 H38 0.9800 . ?
C55 H39 0.9800 . ?
C60 C62 1.419(14) . ?
C60 C61 1.707(14) . ?
C60 H71 0.9900 . ?
C60 H72 0.9900 . ?
C61 H73 0.9900 . ?
C61 H74 0.9900 . ?
C56 H75 0.9900 . ?
C56 H76 0.9900 . ?
C62 H40 0.9800 . ?
C62 H41 0.9800 . ?
C62 H42 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
C5 O3 B2 121.6(4) . . ?
C15 N3 C7 111.7(4) . . ?
C15 N3 H43 124.2 . . ?
C7 N3 H43 124.2 . . ?
O3 C5 C10 119.2(4) . . ?
O3 C5 C7 119.0(4) . . ?
C10 C5 C7 121.9(5) . . ?
C12 N4 C11 110.1(5) . . ?
C12 N4 H44 124.9 . . ?
C11 N4 H44 124.9 . . ?
N3 C7 C13 106.9(4) . . ?
N3 C7 C5 121.7(4) . . ?
C13 C7 C5 131.4(5) . . ?
O4 C8 C10 120.4(4) . . ?
O4 C8 C11 116.5(4) . . ?
C10 C8 C11 123.1(5) . . ?
C8 O4 B2 120.4(4) . . ?
C8 C10 C5 122.3(5) . . ?
C8 C10 H45 118.8 . . ?
C5 C10 H45 118.8 . . ?
N4 C11 C44 107.1(4) . . ?
N4 C11 C8 121.7(4) . . ?
C44 C11 C8 131.0(5) . . ?
N4 C12 C16 107.3(5) . . ?
N4 C12 C22 120.5(6) . . ?
C16 C12 C22 132.2(5) . . ?
C17 C13 C7 105.9(5) . . ?
C17 C13 C19 126.2(5) . . ?
C7 C13 C19 127.9(5) . . ?
C16 C44 C11 105.9(5) . . ?
C16 C44 C18 126.6(5) . . ?
C11 C44 C18 127.4(5) . . ?
N3 C15 C17 105.6(5) . . ?
N3 C15 C21 122.8(5) . . ?
C17 C15 C21 131.6(5) . . ?
C12 C16 C44 109.5(5) . . ?
C12 C16 H46 125.2 . . ?
C44 C16 H46 125.2 . . ?
C13 C17 C15 110.0(5) . . ?
C13 C17 H47 125.0 . . ?
C15 C17 H47 125.0 . . ?
C44 C18 H1 109.5 . . ?
C44 C18 H2 109.5 . . ?
H1 C18 H2 109.5 . . ?
C44 C18 H3 109.5 . . ?
H1 C18 H3 109.5 . . ?
H2 C18 H3 109.5 . . ?
C13 C19 H4 109.5 . . ?
C13 C19 H5 109.5 . . ?
H4 C19 H5 109.5 . . ?
C13 C19 H6 109.5 . . ?
H4 C19 H6 109.5 . . ?
H5 C19 H6 109.5 . . ?
F4 B2 F5 109.8(5) . . ?
F4 B2 O3 108.1(5) . . ?
F5 B2 O3 109.1(5) . . ?
F4 B2 O4 106.8(5) . . ?
F5 B2 O4 109.6(5) . . ?
O3 B2 O4 113.4(5) . . ?
C15 C21 H7 109.5 . . ?
C15 C21 H8 109.5 . . ?
H7 C21 H8 109.5 . . ?
C15 C21 H9 109.5 . . ?
H7 C21 H9 109.5 . . ?
H8 C21 H9 109.5 . . ?
C12 C22 H10 109.5 . . ?
C12 C22 H11 109.5 . . ?
H10 C22 H11 109.5 . . ?
C12 C22 H12 109.5 . . ?
H10 C22 H12 109.5 . . ?
H11 C22 H12 109.5 . . ?
C33 O1 B1 120.5(4) . . ?
C30 O2 B1 118.6(4) . . ?
C34 N2 C31 110.3(5) . . ?
C34 N2 H48 124.9 . . ?
C31 N2 H48 124.9 . . ?
C30 C28 C33 120.8(5) . . ?
C30 C28 H49 119.6 . . ?
C33 C28 H49 119.6 . . ?
C35 N1 C32 110.2(5) . . ?
C35 N1 H50 124.9 . . ?
C32 N1 H50 124.9 . . ?
O2 C30 C28 120.8(4) . . ?
O2 C30 C32 117.1(4) . . ?
C28 C30 C32 122.1(4) . . ?
N2 C31 C36 107.0(4) . . ?
N2 C31 C33 121.8(4) . . ?
C36 C31 C33 131.2(5) . . ?
N1 C32 C40 107.6(4) . . ?
N1 C32 C30 121.0(4) . . ?
C40 C32 C30 131.3(5) . . ?
O1 C33 C28 119.3(4) . . ?
O1 C33 C31 117.7(4) . . ?
C28 C33 C31 122.9(5) . . ?
N2 C34 C37 107.2(5) . . ?
N2 C34 C63 120.8(6) . . ?
C37 C34 C63 132.1(5) . . ?
N1 C35 C39 106.3(5) . . ?
N1 C35 C43 120.6(6) . . ?
C39 C35 C43 133.1(5) . . ?
C37 C36 C31 106.5(5) . . ?
C37 C36 C42 125.8(5) . . ?
C31 C36 C42 127.6(5) . . ?
C34 C37 C36 109.1(5) . . ?
C34 C37 H51 125.5 . . ?
C36 C37 H51 125.5 . . ?
F3 B1 F2 110.9(4) . . ?
F3 B1 O1 108.9(5) . . ?
F2 B1 O1 108.3(4) . . ?
F3 B1 O2 108.6(4) . . ?
F2 B1 O2 108.4(5) . . ?
O1 B1 O2 111.7(4) . . ?
C35 C39 C40 110.3(5) . . ?
C35 C39 H52 124.8 . . ?
C40 C39 H52 124.8 . . ?
C39 C40 C32 105.5(5) . . ?
C39 C40 C41 126.7(5) . . ?
C32 C40 C41 127.7(5) . . ?
C40 C41 H13 109.5 . . ?
C40 C41 H14 109.5 . . ?
H13 C41 H14 109.5 . . ?
C40 C41 H15 109.5 . . ?
H13 C41 H15 109.5 . . ?
H14 C41 H15 109.5 . . ?
C36 C42 H16 109.5 . . ?
C36 C42 H17 109.5 . . ?
H16 C42 H17 109.5 . . ?
C36 C42 H18 109.5 . . ?
H16 C42 H18 109.5 . . ?
H17 C42 H18 109.5 . . ?
C35 C43 H19 109.5 . . ?
C35 C43 H20 109.5 . . ?
H19 C43 H20 109.5 . . ?
C35 C43 H21 109.5 . . ?
H19 C43 H21 109.5 . . ?
H20 C43 H21 109.5 . . ?
C51 N5 C53 112.6(4) . . ?
C51 N5 C52 112.2(5) . . ?
C53 N5 C52 107.6(4) . . ?
C51 N5 C48 108.7(4) . . ?
C53 N5 C48 106.7(4) . . ?
C52 N5 C48 108.9(4) . . ?
C59 C57 H22 109.5 . . ?
C59 C57 H23 109.5 . . ?
H22 C57 H23 109.5 . . ?
C59 C57 H24 109.5 . . ?
H22 C57 H24 109.5 . . ?
H23 C57 H24 109.5 . . ?
C56 C45 H25 109.5 . . ?
C56 C45 H26 109.5 . . ?
H25 C45 H26 109.5 . . ?
C56 C45 H27 109.5 . . ?
H25 C45 H27 109.5 . . ?
H26 C45 H27 109.5 . . ?
C49 C46 H28 109.5 . . ?
C49 C46 H29 109.5 . . ?
H28 C46 H29 109.5 . . ?
C49 C46 H30 109.5 . . ?
H28 C46 H30 109.5 . . ?
H29 C46 H30 109.5 . . ?
C50 C47 C53 114.9(6) . . ?
C50 C47 H53 108.5 . . ?
C53 C47 H53 108.5 . . ?
C50 C47 H54 108.5 . . ?
C53 C47 H54 108.5 . . ?
H53 C47 H54 107.5 . . ?
C61 C58 C59 114.7(7) . . ?
C61 C58 H55 108.6 . . ?
C59 C58 H55 108.6 . . ?
C61 C58 H56 108.6 . . ?
C59 C58 H56 108.6 . . ?
H55 C58 H56 107.6 . . ?
C56 C48 N5 118.7(6) . . ?
C56 C48 H57 107.6 . . ?
N5 C48 H57 107.6 . . ?
C56 C48 H58 107.6 . . ?
N5 C48 H58 107.6 . . ?
H57 C48 H58 107.1 . . ?
C46 C49 C52 115.7(7) . . ?
C46 C49 H59 108.4 . . ?
C52 C49 H59 108.4 . . ?
C46 C49 H60 108.4 . . ?
C52 C49 H60 108.4 . . ?
H59 C49 H60 107.4 . . ?
C34 C63 H31 109.5 . . ?
C34 C63 H32 109.5 . . ?
H31 C63 H32 109.5 . . ?
C34 C63 H33 109.5 . . ?
H31 C63 H33 109.5 . . ?
H32 C63 H33 109.5 . . ?
C47 C50 H34 109.5 . . ?
C47 C50 H35 109.5 . . ?
H34 C50 H35 109.5 . . ?
C47 C50 H36 109.5 . . ?
H34 C50 H36 109.5 . . ?
H35 C50 H36 109.5 . . ?
C54 C51 N5 121.3(7) . . ?
C54 C51 H61 107.0 . . ?
N5 C51 H61 107.0 . . ?
C54 C51 H62 107.0 . . ?
N5 C51 H62 107.0 . . ?
H61 C51 H62 106.8 . . ?
C49 C52 N5 117.8(5) . . ?
C49 C52 H63 107.8 . . ?
N5 C52 H63 107.8 . . ?
C49 C52 H64 107.8 . . ?
N5 C52 H64 107.8 . . ?
H63 C52 H64 107.2 . . ?
C47 C53 N5 116.4(5) . . ?
C47 C53 H65 108.2 . . ?
N5 C53 H65 108.2 . . ?
C47 C53 H66 108.2 . . ?
N5 C53 H66 108.2 . . ?
H65 C53 H66 107.3 . . ?
C51 C54 C55 115.5(7) . . ?
C51 C54 H67 108.4 . . ?
C55 C54 H67 108.4 . . ?
C51 C54 H68 108.4 . . ?
C55 C54 H68 108.4 . . ?
H67 C54 H68 107.5 . . ?
C57 C59 C58 114.1(7) . . ?
C57 C59 H69 108.7 . . ?
C58 C59 H69 108.7 . . ?
C57 C59 H70 108.7 . . ?
C58 C59 H70 108.7 . . ?
H69 C59 H70 107.6 . . ?
C54 C55 H37 109.5 . . ?
C54 C55 H38 109.5 . . ?
H37 C55 H38 109.5 . . ?
C54 C55 H39 109.5 . . ?
H37 C55 H39 109.5 . . ?
H38 C55 H39 109.5 . . ?
C62 C60 C61 108.1(9) . . ?
C62 C60 H71 110.1 . . ?
C61 C60 H71 110.1 . . ?
C62 C60 H72 110.1 . . ?
C61 C60 H72 110.1 . . ?
H71 C60 H72 108.4 . . ?
C58 C61 C60 118.7(7) . . ?
C58 C61 H73 107.6 . . ?
C60 C61 H73 107.6 . . ?
C58 C61 H74 107.6 . . ?
C60 C61 H74 107.6 . . ?
H73 C61 H74 107.1 . . ?
C48 C56 C45 114.1(6) . . ?
C48 C56 H75 108.7 . . ?
C45 C56 H75 108.7 . . ?
C48 C56 H76 108.7 . . ?
C45 C56 H76 108.7 . . ?
H75 C56 H76 107.6 . . ?
C60 C62 H40 109.5 . . ?
C60 C62 H41 109.5 . . ?
H40 C62 H41 109.5 . . ?
C60 C62 H42 109.5 . . ?
H40 C62 H42 109.5 . . ?
H41 C62 H42 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
B2 O3 C5 C10 2.4(7) . . . . ?
B2 O3 C5 C7 -178.2(5) . . . . ?
C15 N3 C7 C13 0.1(5) . . . . ?
C15 N3 C7 C5 179.9(4) . . . . ?
O3 C5 C7 N3 179.8(4) . . . . ?
C10 C5 C7 N3 -0.8(7) . . . . ?
O3 C5 C7 C13 -0.4(8) . . . . ?
C10 C5 C7 C13 179.0(5) . . . . ?
C10 C8 O4 B2 -11.6(8) . . . . ?
C11 C8 O4 B2 168.1(5) . . . . ?
O4 C8 C10 C5 -1.6(7) . . . . ?
C11 C8 C10 C5 178.7(4) . . . . ?
O3 C5 C10 C8 6.5(7) . . . . ?
C7 C5 C10 C8 -172.9(4) . . . . ?
C12 N4 C11 C44 -0.5(5) . . . . ?
C12 N4 C11 C8 175.7(4) . . . . ?
O4 C8 C11 N4 177.7(5) . . . . ?
C10 C8 C11 N4 -2.6(7) . . . . ?
O4 C8 C11 C44 -7.2(8) . . . . ?
C10 C8 C11 C44 172.5(5) . . . . ?
C11 N4 C12 C16 0.4(6) . . . . ?
C11 N4 C12 C22 -179.0(5) . . . . ?
N3 C7 C13 C17 0.4(5) . . . . ?
C5 C7 C13 C17 -179.4(5) . . . . ?
N3 C7 C13 C19 -179.8(5) . . . . ?
C5 C7 C13 C19 0.4(9) . . . . ?
N4 C11 C44 C16 0.3(5) . . . . ?
C8 C11 C44 C16 -175.3(5) . . . . ?
N4 C11 C44 C18 177.0(5) . . . . ?
C8 C11 C44 C18 1.4(9) . . . . ?
C7 N3 C15 C17 -0.6(5) . . . . ?
C7 N3 C15 C21 179.5(5) . . . . ?
N4 C12 C16 C44 -0.2(6) . . . . ?
C22 C12 C16 C44 179.1(6) . . . . ?
C11 C44 C16 C12 -0.1(6) . . . . ?
C18 C44 C16 C12 -176.8(5) . . . . ?
C7 C13 C17 C15 -0.8(6) . . . . ?
C19 C13 C17 C15 179.4(5) . . . . ?
N3 C15 C17 C13 0.9(6) . . . . ?
C21 C15 C17 C13 -179.2(6) . . . . ?
C5 O3 B2 F4 -132.2(5) . . . . ?
C5 O3 B2 F5 108.4(6) . . . . ?
C5 O3 B2 O4 -14.1(8) . . . . ?
C8 O4 B2 F4 137.7(5) . . . . ?
C8 O4 B2 F5 -103.4(6) . . . . ?
C8 O4 B2 O3 18.8(8) . . . . ?
B1 O2 C30 C28 -15.0(6) . . . . ?
B1 O2 C30 C32 167.4(4) . . . . ?
C33 C28 C30 O2 -5.6(7) . . . . ?
C33 C28 C30 C32 171.9(4) . . . . ?
C34 N2 C31 C36 -0.5(5) . . . . ?
C34 N2 C31 C33 179.1(4) . . . . ?
C35 N1 C32 C40 -1.3(6) . . . . ?
C35 N1 C32 C30 176.6(4) . . . . ?
O2 C30 C32 N1 167.5(4) . . . . ?
C28 C30 C32 N1 -10.1(7) . . . . ?
O2 C30 C32 C40 -15.2(8) . . . . ?
C28 C30 C32 C40 167.3(5) . . . . ?
B1 O1 C33 C28 12.8(6) . . . . ?
B1 O1 C33 C31 -170.1(4) . . . . ?
C30 C28 C33 O1 6.9(7) . . . . ?
C30 C28 C33 C31 -170.1(4) . . . . ?
N2 C31 C33 O1 -170.2(4) . . . . ?
C36 C31 C33 O1 9.3(8) . . . . ?
N2 C31 C33 C28 6.8(7) . . . . ?
C36 C31 C33 C28 -173.7(5) . . . . ?
C31 N2 C34 C37 0.7(6) . . . . ?
C31 N2 C34 C63 -178.4(5) . . . . ?
C32 N1 C35 C39 1.0(6) . . . . ?
C32 N1 C35 C43 179.2(5) . . . . ?
N2 C31 C36 C37 0.1(5) . . . . ?
C33 C31 C36 C37 -179.5(5) . . . . ?
N2 C31 C36 C42 -176.7(5) . . . . ?
C33 C31 C36 C42 3.7(9) . . . . ?
N2 C34 C37 C36 -0.7(6) . . . . ?
C63 C34 C37 C36 178.3(5) . . . . ?
C31 C36 C37 C34 0.4(6) . . . . ?
C42 C36 C37 C34 177.2(5) . . . . ?
C33 O1 B1 F3 -150.9(4) . . . . ?
C33 O1 B1 F2 88.4(5) . . . . ?
C33 O1 B1 O2 -30.9(6) . . . . ?
C30 O2 B1 F3 151.8(4) . . . . ?
C30 O2 B1 F2 -87.6(5) . . . . ?
C30 O2 B1 O1 31.7(6) . . . . ?
N1 C35 C39 C40 -0.3(6) . . . . ?
C43 C35 C39 C40 -178.2(6) . . . . ?
C35 C39 C40 C32 -0.4(6) . . . . ?
C35 C39 C40 C41 -178.9(5) . . . . ?
N1 C32 C40 C39 1.0(6) . . . . ?
C30 C32 C40 C39 -176.6(5) . . . . ?
N1 C32 C40 C41 179.5(5) . . . . ?
C30 C32 C40 C41 1.9(9) . . . . ?
C51 N5 C48 C56 174.6(6) . . . . ?
C53 N5 C48 C56 52.9(7) . . . . ?
C52 N5 C48 C56 -63.0(7) . . . . ?
C53 N5 C51 C54 47.5(7) . . . . ?
C52 N5 C51 C54 169.1(5) . . . . ?
C48 N5 C51 C54 -70.4(7) . . . . ?
C46 C49 C52 N5 -175.1(5) . . . . ?
C51 N5 C52 C49 57.0(7) . . . . ?
C53 N5 C52 C49 -178.6(5) . . . . ?
C48 N5 C52 C49 -63.4(7) . . . . ?
C50 C47 C53 N5 -179.9(5) . . . . ?
C51 N5 C53 C47 50.3(7) . . . . ?
C52 N5 C53 C47 -73.8(6) . . . . ?
C48 N5 C53 C47 169.5(5) . . . . ?
N5 C51 C54 C55 -172.8(6) . . . . ?
C61 C58 C59 C57 -173.1(6) . . . . ?
C59 C58 C61 C60 178.9(6) . . . . ?
C62 C60 C61 C58 -74.3(10) . . . . ?
N5 C48 C56 C45 167.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H8 F5 0.98 2.25 3.210(7) 166.7 3_756
C63 H32 F2 0.98 2.61 3.397(7) 137.4 3_557
N3 H43 Cl1 0.88 2.45 3.327(5) 176.4 .
N4 H44 Cl1 0.88 2.37 3.248(5) 174.8 .
C10 H45 Cl1 0.95 2.55 3.500(5) 173.6 .
C21 H8 F5 0.98 2.25 3.210(7) 166.7 3_756
N2 H48 Cl1 0.88 2.43 3.313(5) 177.9 1_455
C28 H49 Cl1 0.95 2.60 3.488(5) 156.4 1_455
N1 H50 Cl1 0.88 2.38 3.253(5) 172.4 1_455
C63 H32 F2 0.98 2.61 3.397(7) 137.4 3_557
C47 H54 F4 0.99 2.61 3.580(8) 167.2 3_656
C48 H58 F4 0.99 2.29 3.177(7) 148.8 2_656
C52 H63 F2 0.99 2.48 3.436(7) 161.6 4_565
C52 H64 F4 0.99 2.31 3.278(6) 165.6 3_656
C54 H67 F3 0.99 2.64 3.369(8) 130.4 .
C56 H75 F2 0.99 2.56 3.375(8) 139.0 4_565

_refine_diff_density_max         0.947
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_60404m
_database_code_depnum_ccdc_archive 'CCDC 1533942'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-03-17 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         
'C27 H25 B F2 N2 O2, C28 H30 N3, 0.191(C6), 1.309(C Cl2), Cl'
_chemical_formula_sum            'C57.46 H55 B Cl3.62 F2 N5 O2'
_chemical_formula_weight         1024.59

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'
Cl Cl 0.3639 0.7018 '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'
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'

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

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

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

_cell_length_a                   8.5862(12)
_cell_length_b                   19.717(2)
_cell_length_c                   31.483(3)
_cell_angle_alpha                72.702(9)
_cell_angle_beta                 85.311(12)
_cell_angle_gamma                88.492(12)
_cell_volume                     5071.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2665
_cell_measurement_theta_min      25.39
_cell_measurement_theta_max      68.25

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             2141
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.389
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            62082
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         6.544
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_full        65.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             16843
_reflns_number_gt                8790
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1906P)²-2.0000P] 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         16843
_refine_ls_number_parameters     1306
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0934
_refine_ls_wR_factor_ref         0.2912
_refine_ls_wR_factor_gt          0.2549
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.023
_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 0.8111(7) 0.7330(3) -0.0235(2) 0.0579(16) Uani 1 1 d . . . . .
H1 H 0.7983 0.7640 -0.0054 0.069 Uiso 1 1 calc R U . . .
C2 C 0.7491(9) 0.7518(4) -0.0650(2) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.6971 0.7961 -0.0756 0.091 Uiso 1 1 calc R U . . .
C3 C 0.7633(10) 0.7064(5) -0.0904(2) 0.085(2) Uani 1 1 d . . . . .
H3 H 0.7190 0.7191 -0.1184 0.102 Uiso 1 1 calc R U . . .
C4 C 0.8410(10) 0.6421(5) -0.0762(2) 0.081(2) Uani 1 1 d . . . . .
H4 H 0.8509 0.6108 -0.0941 0.097 Uiso 1 1 calc R U . . .
C5 C 0.9031(9) 0.6249(4) -0.0357(2) 0.072(2) Uani 1 1 d . . . . .
H5 H 0.9566 0.5810 -0.0257 0.086 Uiso 1 1 calc R U . . .
C6 C 0.8908(7) 0.6698(3) -0.00831(17) 0.0496(15) Uani 1 1 d . . . . .
C7 C 0.9625(6) 0.6495(3) 0.03429(16) 0.0422(13) Uani 1 1 d . . . . .
C8 C 0.9500(6) 0.5825(3) 0.06725(16) 0.0394(13) Uani 1 1 d . . . . .
C9 C 1.0427(6) 0.5859(3) 0.10111(16) 0.0368(12) Uani 1 1 d . . . . .
N1 N 1.1102(5) 0.6524(2) 0.08887(13) 0.0389(10) Uani 1 1 d . . . . .
H6 H 1.1744 0.6674 0.1046 0.047 Uiso 1 1 calc R U . . .
C10 C 1.0618(7) 0.6910(3) 0.04872(16) 0.0437(13) Uani 1 1 d . . . . .
C11 C 1.1220(8) 0.7655(3) 0.02696(19) 0.0610(17) Uani 1 1 d . . . . .
H73 H 1.0757 0.7856 -0.0016 0.091 Uiso 1 1 calc R U . . .
H74 H 1.0934 0.7950 0.0466 0.091 Uiso 1 1 calc R U . . .
H75 H 1.2360 0.7643 0.0218 0.091 Uiso 1 1 calc R U . . .
C12 C 0.8488(7) 0.5218(3) 0.06749(19) 0.0510(15) Uani 1 1 d . . . . .
H76 H 0.7968 0.5335 0.0396 0.077 Uiso 1 1 calc R U . . .
H77 H 0.9132 0.4792 0.0702 0.077 Uiso 1 1 calc R U . . .
H78 H 0.7698 0.5130 0.0928 0.077 Uiso 1 1 calc R U . . .
C13 C 1.0707(6) 0.5360(3) 0.14258(15) 0.0322(11) Uani 1 1 d . . . . .
C14 C 1.1451(6) 0.5534(3) 0.17435(15) 0.0366(12) Uani 1 1 d . . . . .
H7 H 1.1814 0.6007 0.1685 0.044 Uiso 1 1 calc R U . . .
C15 C 1.1696(5) 0.5044(2) 0.21492(15) 0.0267(10) Uani 1 1 d . . . . .
O1 O 1.1225(4) 0.43885(17) 0.22371(10) 0.0381(8) Uani 1 1 d . . . . .
O2 O 1.0200(5) 0.47037(18) 0.14958(11) 0.0454(9) Uani 1 1 d . . . . .
B1 B 1.0477(7) 0.4133(3) 0.19034(17) 0.0282(12) Uani 1 1 d . . . . .
F1 F 1.1471(4) 0.36439(17) 0.17931(10) 0.0538(9) Uani 1 1 d . . . . .
F2 F 0.9089(3) 0.38244(15) 0.20916(9) 0.0439(7) Uani 1 1 d . . . . .
C16 C 1.2472(5) 0.5217(2) 0.24881(14) 0.0259(10) Uani 1 1 d . . . . .
C17 C 1.2689(5) 0.4835(2) 0.29272(14) 0.0259(10) Uani 1 1 d . . . . .
C18 C 1.3462(5) 0.5288(2) 0.31160(15) 0.0277(10) Uani 1 1 d . . . . .
C19 C 1.3692(5) 0.5938(2) 0.27819(15) 0.0294(11) Uani 1 1 d . . . . .
N2 N 1.3098(5) 0.58854(19) 0.24144(12) 0.0304(9) Uani 1 1 d . . . . .
H8 H 1.3103 0.6228 0.2160 0.036 Uiso 1 1 calc R U . . .
C20 C 1.2149(6) 0.4089(2) 0.31507(15) 0.0295(10) Uani 1 1 d . . . . .
H79 H 1.2442 0.3938 0.3459 0.044 Uiso 1 1 calc R U . . .
H80 H 1.1011 0.4067 0.3149 0.044 Uiso 1 1 calc R U . . .
H81 H 1.2642 0.3773 0.2990 0.044 Uiso 1 1 calc R U . . .
C21 C 1.4470(6) 0.6599(3) 0.27858(17) 0.0390(12) Uani 1 1 d . . . . .
H82 H 1.4830 0.6539 0.3082 0.058 Uiso 1 1 calc R U . . .
H83 H 1.5367 0.6699 0.2563 0.058 Uiso 1 1 calc R U . . .
H84 H 1.3728 0.6995 0.2714 0.058 Uiso 1 1 calc R U . . .
C22 C 1.3771(5) 0.5131(2) 0.35858(15) 0.0280(10) Uani 1 1 d . . . . .
C23 C 1.4288(5) 0.4463(2) 0.38320(15) 0.0321(11) Uani 1 1 d . . . . .
H9 H 1.4546 0.4115 0.3684 0.039 Uiso 1 1 calc R U . . .
C24 C 1.4431(6) 0.4299(3) 0.42835(16) 0.0398(12) Uani 1 1 d . . . . .
H10 H 1.4783 0.3840 0.4443 0.048 Uiso 1 1 calc R U . . .
C25 C 1.4065(7) 0.4798(3) 0.45081(17) 0.0476(14) Uani 1 1 d . . . . .
H11 H 1.4135 0.4680 0.4821 0.057 Uiso 1 1 calc R U . . .
C26 C 1.3601(6) 0.5466(3) 0.42704(17) 0.0448(14) Uani 1 1 d . . . . .
H12 H 1.3390 0.5816 0.4420 0.054 Uiso 1 1 calc R U . . .
C27 C 1.3436(6) 0.5636(3) 0.38192(16) 0.0348(11) Uani 1 1 d . . . . .
H13 H 1.3093 0.6098 0.3663 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 1.27908(15) 0.73070(6) 0.15214(4) 0.0396(3) Uani 1 1 d . . . . .
C28 C 0.9250(8) 0.6703(3) 0.2423(3) 0.0616(18) Uani 1 1 d . . . . .
H14 H 0.9408 0.7137 0.2191 0.074 Uiso 1 1 calc R U . . .
C29 C 0.9866(7) 0.6604(3) 0.2820(3) 0.0598(18) Uani 1 1 d . . . . .
H15 H 1.0442 0.6984 0.2859 0.072 Uiso 1 1 calc R U . . .
C30 C 0.9709(6) 0.5989(4) 0.3169(2) 0.0592(18) Uani 1 1 d . . . . .
H16 H 1.0135 0.5952 0.3445 0.071 Uiso 1 1 calc R U . . .
C31 C 0.8887(6) 0.5408(3) 0.3108(2) 0.0501(15) Uani 1 1 d . . . . .
C32 C 0.8208(6) 0.5505(3) 0.2701(2) 0.0454(14) Uani 1 1 d . . . . .
C33 C 0.8389(7) 0.6164(3) 0.2360(2) 0.0559(16) Uani 1 1 d . . . . .
C34 C 0.6825(7) 0.5725(3) 0.1895(2) 0.0515(15) Uani 1 1 d . . . . .
C35 C 0.6076(7) 0.5835(3) 0.1507(2) 0.0518(15) Uani 1 1 d . . . . .
H17 H 0.6131 0.6282 0.1283 0.062 Uiso 1 1 calc R U . . .
C36 C 0.5240(7) 0.5274(3) 0.14533(19) 0.0485(14) Uani 1 1 d . . . . .
H18 H 0.4718 0.5353 0.1188 0.058 Uiso 1 1 calc R U . . .
C39 C 0.6675(6) 0.5053(3) 0.22303(19) 0.0416(13) Uani 1 1 d . . . . .
C42 C 0.7024(7) 0.2978(3) 0.3604(2) 0.0525(15) Uani 1 1 d . . . . .
H19 H 0.6969 0.2527 0.3823 0.063 Uiso 1 1 calc R U . . .
C43 C 0.7794(6) 0.3531(3) 0.3695(2) 0.0505(15) Uani 1 1 d . . . . .
H20 H 0.8216 0.3458 0.3975 0.061 Uiso 1 1 calc R U . . .
C44 C 0.7933(6) 0.4189(3) 0.3371(2) 0.0442(14) Uani 1 1 d . . . . .
C45 C 0.7245(6) 0.4285(3) 0.2966(2) 0.0439(14) Uani 1 1 d . . . . .
C46 C 0.7369(6) 0.4946(3) 0.2636(2) 0.0424(13) Uani 1 1 d . . . . .
C47 C 0.9518(7) 0.4660(4) 0.3843(2) 0.0625(18) Uani 1 1 d . . . . .
H45 H 1.0485 0.4948 0.3778 0.075 Uiso 1 1 calc R U . . .
H46 H 0.9810 0.4155 0.3969 0.075 Uiso 1 1 calc R U . . .
C48 C 0.8423(8) 0.4889(5) 0.4177(3) 0.091(3) Uani 1 1 d . . . . .
H47 H 0.8133 0.5394 0.4049 0.109 Uiso 1 1 calc R U . . .
H48 H 0.7456 0.4602 0.4239 0.109 Uiso 1 1 calc R U . . .
C49 C 0.9179(13) 0.4796(7) 0.4605(3) 0.137(4) Uani 1 1 d . . . . .
H85 H 0.8450 0.4948 0.4815 0.206 Uiso 1 1 calc R U . . .
H86 H 0.9451 0.4295 0.4734 0.206 Uiso 1 1 calc R U . . .
H87 H 1.0128 0.5086 0.4544 0.206 Uiso 1 1 calc R U . . .
C50 C 0.8325(9) 0.6896(6) 0.1548(4) 0.130(4) Uani 1 1 d . . . . .
H49 H 0.9395 0.7040 0.1580 0.156 Uiso 1 1 calc R U . . .
H50 H 0.8321 0.6773 0.1266 0.156 Uiso 1 1 calc R U . . .
C51 C 0.7268(10) 0.7432(5) 0.1556(3) 0.104(3) Uani 1 1 d . . . . .
H51 H 0.7324 0.7586 0.1826 0.125 Uiso 1 1 calc R U . . .
H52 H 0.6186 0.7283 0.1542 0.125 Uiso 1 1 calc R U . . .
C52 C 0.7869(10) 0.8076(4) 0.1093(3) 0.100(3) Uani 1 1 d . . . . .
H88 H 0.7191 0.8493 0.1063 0.150 Uiso 1 1 calc R U . . .
H89 H 0.8947 0.8206 0.1114 0.150 Uiso 1 1 calc R U . . .
H90 H 0.7819 0.7905 0.0832 0.150 Uiso 1 1 calc R U . . .
B2 B 0.4463(7) 1.0778(3) 0.31414(18) 0.0326(13) Uani 1 1 d . . . . .
N3 N 0.7729(7) 0.6232(3) 0.1971(2) 0.0722(17) Uani 1 1 d . . . . .
C37 C 0.5126(6) 0.4616(3) 0.17599(18) 0.0411(13) Uani 1 1 d . . . . .
H21 H 0.4586 0.4244 0.1700 0.049 Uiso 1 1 calc R U . . .
C38 C 0.5817(6) 0.4498(3) 0.21636(18) 0.0367(12) Uani 1 1 d . . . . .
N4 N 0.5687(4) 0.3856(2) 0.24950(14) 0.0347(10) Uani 1 1 d . . . . .
C40 C 0.6408(6) 0.3721(3) 0.28891(18) 0.0396(13) Uani 1 1 d . . . . .
C41 C 0.6348(6) 0.3056(3) 0.32133(18) 0.0430(13) Uani 1 1 d . . . . .
H22 H 0.5846 0.2666 0.3163 0.052 Uiso 1 1 calc R U . . .
N5 N 0.8754(5) 0.4753(3) 0.34306(17) 0.0525(13) Uani 1 1 d . . . . .
C53 C 0.4757(6) 0.3287(2) 0.24191(17) 0.0352(11) Uani 1 1 d . . . . .
H53 H 0.3832 0.3500 0.2260 0.042 Uiso 1 1 calc R U . . .
H54 H 0.4381 0.2955 0.2710 0.042 Uiso 1 1 calc R U . . .
C54 C 0.5717(6) 0.2877(3) 0.21458(18) 0.0377(12) Uani 1 1 d . . . . .
H55 H 0.6210 0.3215 0.1872 0.045 Uiso 1 1 calc R U . . .
H56 H 0.6558 0.2609 0.2322 0.045 Uiso 1 1 calc R U . . .
C55 C 0.4691(6) 0.2371(3) 0.20215(17) 0.0387(12) Uani 1 1 d . . . . .
H91 H 0.5321 0.2112 0.1847 0.058 Uiso 1 1 calc R U . . .
H92 H 0.4215 0.2034 0.2293 0.058 Uiso 1 1 calc R U . . .
H93 H 0.3868 0.2639 0.1844 0.058 Uiso 1 1 calc R U . . .
C56 C 0.1541(6) 0.9377(3) 0.11640(16) 0.0351(11) Uani 1 1 d . . . . .
H23 H 0.1778 0.8904 0.1330 0.042 Uiso 1 1 calc R U . . .
C57 C 0.1386(7) 0.9545(3) 0.07085(17) 0.0462(14) Uani 1 1 d . . . . .
H24 H 0.1517 0.9184 0.0565 0.055 Uiso 1 1 calc R U . . .
C58 C 0.1043(6) 1.0232(3) 0.04600(17) 0.0448(13) Uani 1 1 d . . . . .
H25 H 0.0954 1.0344 0.0148 0.054 Uiso 1 1 calc R U . . .
C59 C 0.0832(6) 1.0753(3) 0.06719(16) 0.0407(13) Uani 1 1 d . . . . .
H26 H 0.0593 1.1225 0.0504 0.049 Uiso 1 1 calc R U . . .
C60 C 0.0964(6) 1.0593(3) 0.11259(15) 0.0334(11) Uani 1 1 d . . . . .
H27 H 0.0794 1.0956 0.1267 0.040 Uiso 1 1 calc R U . . .
C61 C 0.1345(5) 0.9909(2) 0.13806(14) 0.0264(10) Uani 1 1 d . . . . .
C62 C 0.1585(5) 0.9751(2) 0.18563(15) 0.0273(10) Uani 1 1 d . . . . .
C63 C 0.2410(5) 1.0165(2) 0.20613(14) 0.0261(10) Uani 1 1 d . . . . .
C64 C 0.2473(5) 0.9773(2) 0.25080(14) 0.0251(10) Uani 1 1 d . . . . .
N6 N 0.1709(4) 0.91400(18) 0.25716(12) 0.0266(8) Uani 1 1 d . . . . .
H28 H 0.1584 0.8802 0.2827 0.032 Uiso 1 1 calc R U . . .
C65 C 0.1185(5) 0.9114(2) 0.21881(15) 0.0281(10) Uani 1 1 d . . . . .
C66 C 0.0305(6) 0.8485(2) 0.21665(16) 0.0337(11) Uani 1 1 d . . . . .
H94 H 0.0017 0.8559 0.1861 0.050 Uiso 1 1 calc R U . . .
H95 H 0.0962 0.8059 0.2255 0.050 Uiso 1 1 calc R U . . .
H96 H -0.0644 0.8422 0.2370 0.050 Uiso 1 1 calc R U . . .
C67 C 0.3116(6) 1.0879(2) 0.18424(15) 0.0297(11) Uani 1 1 d . . . . .
H97 H 0.2901 1.1035 0.1527 0.045 Uiso 1 1 calc R U . . .
H98 H 0.2664 1.1219 0.1990 0.045 Uiso 1 1 calc R U . . .
H99 H 0.4248 1.0850 0.1866 0.045 Uiso 1 1 calc R U . . .
C68 C 0.3206(5) 0.9920(2) 0.28647(15) 0.0272(10) Uani 1 1 d . . . . .
C69 C 0.3198(6) 0.9440(2) 0.32874(14) 0.0299(11) Uani 1 1 d . . . . .
H29 H 0.2571 0.9025 0.3360 0.036 Uiso 1 1 calc R U . . .
C70 C 0.4088(6) 0.9556(2) 0.36034(15) 0.0294(11) Uani 1 1 d . . . . .
O3 O 0.4823(4) 1.01665(17) 0.35278(10) 0.0362(8) Uani 1 1 d . . . . .
O4 O 0.3949(4) 1.05303(16) 0.27717(10) 0.0316(8) Uani 1 1 d . . . . .
F3 F 0.3255(4) 1.11612(15) 0.32751(9) 0.0469(8) Uani 1 1 d . . . . .
F4 F 0.5773(4) 1.11778(14) 0.29913(9) 0.0450(7) Uani 1 1 d . . . . .
C71 C 0.4327(6) 0.9028(3) 0.40184(15) 0.0332(11) Uani 1 1 d . . . . .
C72 C 0.5122(6) 0.9055(3) 0.43782(15) 0.0375(12) Uani 1 1 d . . . . .
C73 C 0.4960(6) 0.8371(3) 0.46949(17) 0.0403(13) Uani 1 1 d . . . . .
C74 C 0.4123(7) 0.7952(3) 0.45106(16) 0.0394(12) Uani 1 1 d . . . . .
N7 N 0.3720(5) 0.8347(2) 0.41104(12) 0.0374(10) Uani 1 1 d . . . . .
H30 H 0.3161 0.8200 0.3933 0.045 Uiso 1 1 calc R U . . .
C75 C 0.6005(7) 0.9661(3) 0.44227(18) 0.0487(15) Uani 1 1 d . . . . .
H100 H 0.6447 0.9527 0.4714 0.073 Uiso 1 1 calc R U . . .
H101 H 0.6852 0.9789 0.4185 0.073 Uiso 1 1 calc R U . . .
H102 H 0.5302 1.0068 0.4399 0.073 Uiso 1 1 calc R U . . .
C76 C 0.3656(8) 0.7192(3) 0.46998(19) 0.0546(16) Uani 1 1 d . . . . .
H103 H 0.4060 0.6996 0.4994 0.082 Uiso 1 1 calc R U . . .
H104 H 0.2514 0.7157 0.4729 0.082 Uiso 1 1 calc R U . . .
H105 H 0.4088 0.6923 0.4501 0.082 Uiso 1 1 calc R U . . .
C77 C 0.5493(7) 0.8161(3) 0.51526(18) 0.0481(14) Uani 1 1 d . . . . .
C78 C 0.6440(8) 0.7579(3) 0.5304(2) 0.0616(17) Uani 1 1 d . . . . .
H31 H 0.6734 0.7285 0.5120 0.074 Uiso 1 1 calc R U . . .
C79 C 0.6962(9) 0.7423(4) 0.5731(2) 0.070(2) Uani 1 1 d . . . . .
H32 H 0.7619 0.7022 0.5834 0.084 Uiso 1 1 calc R U . . .
C80 C 0.6564(10) 0.7824(4) 0.6003(3) 0.085(3) Uani 1 1 d . . . . .
H33 H 0.6960 0.7714 0.6289 0.102 Uiso 1 1 calc R U . . .
C81 C 0.5570(11) 0.8399(4) 0.5861(2) 0.088(3) Uani 1 1 d . . . . .
H34 H 0.5261 0.8683 0.6051 0.105 Uiso 1 1 calc R U . . .
C82 C 0.5037(9) 0.8553(3) 0.54422(19) 0.0642(18) Uani 1 1 d . . . . .
H35 H 0.4335 0.8939 0.5348 0.077 Uiso 1 1 calc R U . . .
Cl2 Cl 0.18629(15) 0.76975(6) 0.34384(4) 0.0377(3) Uani 1 1 d . . . . .
C83 C 0.5398(7) 0.9339(3) 0.1550(2) 0.0516(15) Uani 1 1 d . . . . .
H36 H 0.5079 0.9424 0.1257 0.062 Uiso 1 1 calc R U . . .
C84 C 0.5018(6) 0.8716(3) 0.1869(2) 0.0519(16) Uani 1 1 d . . . . .
H37 H 0.4436 0.8375 0.1790 0.062 Uiso 1 1 calc R U . . .
C85 C 0.5435(6) 0.8560(3) 0.2300(2) 0.0502(15) Uani 1 1 d . . . . .
H38 H 0.5134 0.8123 0.2514 0.060 Uiso 1 1 calc R U . . .
C86 C 0.6308(6) 0.9052(3) 0.24155(19) 0.0407(13) Uani 1 1 d . . . . .
C87 C 0.6733(6) 0.9707(3) 0.20902(19) 0.0392(13) Uani 1 1 d . . . . .
C88 C 0.6245(6) 0.9843(3) 0.16526(19) 0.0437(13) Uani 1 1 d . . . . .
N8 N 0.6782(5) 0.8928(2) 0.28488(16) 0.0417(11) Uani 1 1 d . . . . .
C89 C 0.7756(6) 0.9388(2) 0.29586(17) 0.0350(12) Uani 1 1 d . . . . .
C90 C 0.8343(7) 0.9232(3) 0.33734(19) 0.0459(14) Uani 1 1 d . . . . .
H39 H 0.8125 0.8787 0.3591 0.055 Uiso 1 1 calc R U . . .
C91 C 0.9247(6) 0.9728(3) 0.34666(18) 0.0408(13) Uani 1 1 d . . . . .
H40 H 0.9652 0.9612 0.3751 0.049 Uiso 1 1 calc R U . . .
C92 C 0.9597(6) 1.0386(3) 0.31669(16) 0.0350(11) Uani 1 1 d . . . . .
H41 H 1.0194 1.0719 0.3250 0.042 Uiso 1 1 calc R U . . .
C93 C 0.9065(5) 1.0555(2) 0.27440(15) 0.0297(11) Uani 1 1 d . . . . .
C94 C 0.8139(5) 1.0052(2) 0.26322(16) 0.0317(11) Uani 1 1 d . . . . .
C95 C 0.7605(5) 1.0201(2) 0.22073(17) 0.0326(11) Uani 1 1 d . . . . .
N9 N 0.9394(4) 1.11961(19) 0.24229(13) 0.0307(9) Uani 1 1 d . . . . .
C96 C 0.8819(6) 1.1380(2) 0.20047(16) 0.0316(11) Uani 1 1 d . . . . .
C97 C 0.9057(6) 1.2044(3) 0.16980(17) 0.0395(12) Uani 1 1 d . . . . .
H42 H 0.9603 1.2398 0.1775 0.047 Uiso 1 1 calc R U . . .
C98 C 0.8498(6) 1.2191(3) 0.12806(18) 0.0438(13) Uani 1 1 d . . . . .
H43 H 0.8670 1.2650 0.1075 0.053 Uiso 1 1 calc R U . . .
C99 C 0.7698(6) 1.1696(3) 0.11502(18) 0.0448(13) Uani 1 1 d . . . . .
H44 H 0.7357 1.1808 0.0858 0.054 Uiso 1 1 calc R U . . .
C100 C 0.7397(6) 1.1024(3) 0.14576(18) 0.0420(13) Uani 1 1 d . . . . .
C101 C 0.7937(6) 1.0870(3) 0.18888(17) 0.0343(11) Uani 1 1 d . . . . .
N10 N 0.6613(6) 1.0508(2) 0.13452(16) 0.0529(13) Uani 1 1 d . . . . .
C102 C 0.6190(7) 0.8300(3) 0.3202(2) 0.0538(16) Uani 1 1 d . . . . .
H57 H 0.5135 0.8188 0.3137 0.065 Uiso 1 1 calc R U . . .
H58 H 0.6085 0.8414 0.3489 0.065 Uiso 1 1 calc R U . . .
C103 C 0.7222(7) 0.7647(3) 0.3254(2) 0.0485(14) Uani 1 1 d . . . . .
H59 H 0.8304 0.7762 0.3296 0.058 Uiso 1 1 calc R U . . .
H60 H 0.7242 0.7493 0.2981 0.058 Uiso 1 1 calc R U . . .
C104 C 0.6584(8) 0.7050(3) 0.3657(2) 0.0589(16) Uani 1 1 d . . . . .
H106 H 0.7249 0.6628 0.3691 0.088 Uiso 1 1 calc R U . . .
H107 H 0.6577 0.7203 0.3926 0.088 Uiso 1 1 calc R U . . .
H108 H 0.5517 0.6935 0.3613 0.088 Uiso 1 1 calc R U . . .
C105 C 1.0416(6) 1.1696(2) 0.25385(16) 0.0321(11) Uani 1 1 d . . . . .
H61 H 1.0928 1.2018 0.2261 0.038 Uiso 1 1 calc R U . . .
H62 H 1.1245 1.1425 0.2719 0.038 Uiso 1 1 calc R U . . .
C106 C 0.9503(6) 1.2138(2) 0.28003(17) 0.0332(11) Uani 1 1 d . . . . .
H63 H 0.8802 1.2473 0.2603 0.040 Uiso 1 1 calc R U . . .
H64 H 0.8849 1.1821 0.3051 0.040 Uiso 1 1 calc R U . . .
C107 C 1.0608(6) 1.2549(3) 0.29802(17) 0.0386(12) Uani 1 1 d . . . . .
H109 H 1.0007 1.2829 0.3147 0.058 Uiso 1 1 calc R U . . .
H110 H 1.1292 1.2217 0.3179 0.058 Uiso 1 1 calc R U . . .
H111 H 1.1244 1.2867 0.2732 0.058 Uiso 1 1 calc R U . . .
C108 C 0.5621(13) 1.0742(7) 0.0958(5) 0.039(4) Uani 0.49(2) 1 d . U P A 1
H65 H 0.5382 1.1254 0.0894 0.047 Uiso 0.49(2) 1 calc R U P A 1
H66 H 0.4623 1.0477 0.1031 0.047 Uiso 0.49(2) 1 calc R U P A 1
C109 C 0.6495(14) 1.0602(8) 0.0547(6) 0.050(4) Uani 0.49(2) 1 d . U P A 1
H67 H 0.7449 1.0898 0.0455 0.060 Uiso 0.49(2) 1 calc R U P A 1
H68 H 0.6807 1.0096 0.0615 0.060 Uiso 0.49(2) 1 calc R U P A 1
C110 C 0.545(4) 1.0780(18) 0.0198(11) 0.076(9) Uani 0.49(2) 1 d . U P A 1
H112 H 0.5973 1.0697 -0.0071 0.115 Uiso 0.49(2) 1 calc R U P A 1
H113 H 0.4515 1.0483 0.0292 0.115 Uiso 0.49(2) 1 calc R U P A 1
H114 H 0.5154 1.1282 0.0133 0.115 Uiso 0.49(2) 1 calc R U P A 1
C114 C 0.6727(17) 1.0556(7) 0.0839(6) 0.057(5) Uani 0.51(2) 1 d . U P A 2
H69 H 0.7626 1.0855 0.0679 0.069 Uiso 0.51(2) 1 calc R U P A 2
H70 H 0.6861 1.0078 0.0800 0.069 Uiso 0.51(2) 1 calc R U P A 2
C115 C 0.5219(17) 1.0885(8) 0.0665(6) 0.065(5) Uani 0.51(2) 1 d . U P A 2
H71 H 0.5062 1.1350 0.0723 0.078 Uiso 0.51(2) 1 calc R U P A 2
H72 H 0.4332 1.0573 0.0818 0.078 Uiso 0.51(2) 1 calc R U P A 2
C116 C 0.530(5) 1.0993(15) 0.0122(11) 0.071(7) Uani 0.51(2) 1 d . U P A 2
H115 H 0.4321 1.1208 0.0004 0.106 Uiso 0.51(2) 1 calc R U P A 2
H116 H 0.6175 1.1305 -0.0027 0.106 Uiso 0.51(2) 1 calc R U P A 2
H117 H 0.5446 1.0531 0.0067 0.106 Uiso 0.51(2) 1 calc R U P A 2
Cl6 Cl 0.8501(4) 0.99678(18) 0.55550(10) 0.1424(11) Uani 1 1 d . . . . .
C111 C 0.9231(16) 0.9145(6) 0.5515(6) 0.174(6) Uani 1 1 d . . . . .
Cl7 Cl 1.0749(4) 0.88618(17) 0.58242(11) 0.1398(10) Uani 1 1 d . . . . .
Cl8 Cl -0.0807(3) 0.67748(13) 0.46417(9) 0.1206(9) Uani 1 1 d . . . . .
C112 C -0.0900(12) 0.7698(4) 0.4328(3) 0.103(3) Uani 1 1 d . . . . .
Cl9 Cl -0.0037(3) 0.82231(15) 0.46143(11) 0.1341(10) Uani 1 1 d . . . . .
Cl4 Cl 0.6492(4) 0.46223(17) 0.96881(10) 0.0787(12) Uiso 0.617(5) 1 d . . P B 1
Cl5 Cl 0.6546(5) 0.3444(2) 1.04678(14) 0.1054(15) Uiso 0.617(5) 1 d . . P B 1
C113 C 0.540(2) 0.3862(9) 1.0044(5) 0.102(4) Uiso 0.617(5) 1 d . . P B 1
C119 C 0.6055(15) 0.3780(7) 1.0736(4) 0.037(3) Uiso 0.383(5) 1 d D . P B 2
C120 C 0.689(3) 0.3764(15) 1.0345(5) 0.1054(15) Uiso 0.383(5) 1 d D . P B 2
C121 C 0.640(2) 0.4088(10) 0.9899(5) 0.081(6) Uiso 0.383(5) 1 d D . P B 2
C122 C 0.524(2) 0.3702(11) 0.9779(7) 0.102(4) Uiso 0.383(5) 1 d D . P B 2
C123 C 0.5196(12) 0.3211(5) 0.9595(3) 0.021(3) Uiso 0.383(5) 1 d D . P B 2
C124 C 0.4954(17) 0.2742(7) 0.9381(4) 0.046(4) Uiso 0.383(5) 1 d D . P B 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 C6 1.380(8) . ?
C1 C2 1.396(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.364(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.463(7) . ?
C7 C10 1.387(8) . ?
C7 C8 1.417(7) . ?
C8 C9 1.400(7) . ?
C8 C12 1.495(8) . ?
C9 N1 1.381(7) . ?
C9 C13 1.417(7) . ?
N1 C10 1.359(6) . ?
N1 H6 0.8800 . ?
C10 C11 1.509(8) . ?
C11 H73 0.9800 . ?
C11 H74 0.9800 . ?
C11 H75 0.9800 . ?
C12 H76 0.9800 . ?
C12 H77 0.9800 . ?
C12 H78 0.9800 . ?
C13 O2 1.325(6) . ?
C13 C14 1.359(6) . ?
C14 C15 1.382(6) . ?
C14 H7 0.9500 . ?
C15 O1 1.307(5) . ?
C15 C16 1.430(6) . ?
O1 B1 1.487(6) . ?
O2 B1 1.465(6) . ?
B1 F2 1.360(6) . ?
B1 F1 1.374(6) . ?
C16 N2 1.383(6) . ?
C16 C17 1.389(6) . ?
C17 C18 1.416(6) . ?
C17 C20 1.496(6) . ?
C18 C19 1.401(6) . ?
C18 C22 1.463(6) . ?
C19 N2 1.334(6) . ?
C19 C21 1.484(7) . ?
N2 H8 0.8800 . ?
C20 H79 0.9800 . ?
C20 H80 0.9800 . ?
C20 H81 0.9800 . ?
C21 H82 0.9800 . ?
C21 H83 0.9800 . ?
C21 H84 0.9800 . ?
C22 C23 1.397(6) . ?
C22 C27 1.413(6) . ?
C23 C24 1.376(7) . ?
C23 H9 0.9500 . ?
C24 C25 1.389(7) . ?
C24 H10 0.9500 . ?
C25 C26 1.375(8) . ?
C25 H11 0.9500 . ?
C26 C27 1.377(7) . ?
C26 H12 0.9500 . ?
C27 H13 0.9500 . ?
C28 C29 1.355(9) . ?
C28 C33 1.379(8) . ?
C28 H14 0.9500 . ?
C29 C30 1.375(9) . ?
C29 H15 0.9500 . ?
C30 C31 1.430(8) . ?
C30 H16 0.9500 . ?
C31 N5 1.386(8) . ?
C31 C32 1.409(8) . ?
C32 C46 1.407(7) . ?
C32 C33 1.420(9) . ?
C33 N3 1.362(8) . ?
C34 N3 1.367(7) . ?
C34 C35 1.387(8) . ?
C34 C39 1.428(8) . ?
C35 C36 1.393(8) . ?
C35 H17 0.9500 . ?
C36 C37 1.368(8) . ?
C36 H18 0.9500 . ?
C39 C46 1.409(8) . ?
C39 C38 1.411(7) . ?
C42 C41 1.368(8) . ?
C42 C43 1.403(8) . ?
C42 H19 0.9500 . ?
C43 C44 1.392(8) . ?
C43 H20 0.9500 . ?
C44 N5 1.399(7) . ?
C44 C45 1.407(8) . ?
C45 C46 1.405(8) . ?
C45 C40 1.430(7) . ?
C47 N5 1.462(8) . ?
C47 C48 1.514(9) . ?
C47 H45 0.9900 . ?
C47 H46 0.9900 . ?
C48 C49 1.503(12) . ?
C48 H47 0.9900 . ?
C48 H48 0.9900 . ?
C49 H85 0.9800 . ?
C49 H86 0.9800 . ?
C49 H87 0.9800 . ?
C50 C51 1.379(11) . ?
C50 N3 1.624(12) . ?
C50 H49 0.9900 . ?
C50 H50 0.9900 . ?
C51 C52 1.676(12) . ?
C51 H51 0.9900 . ?
C51 H52 0.9900 . ?
C52 H88 0.9800 . ?
C52 H89 0.9800 . ?
C52 H90 0.9800 . ?
B2 F4 1.359(7) . ?
B2 F3 1.378(6) . ?
B2 O3 1.483(6) . ?
B2 O4 1.491(6) . ?
C37 C38 1.400(7) . ?
C37 H21 0.9500 . ?
C38 N4 1.381(6) . ?
N4 C40 1.383(6) . ?
N4 C53 1.479(6) . ?
C40 C41 1.402(7) . ?
C41 H22 0.9500 . ?
C53 C54 1.529(7) . ?
C53 H53 0.9900 . ?
C53 H54 0.9900 . ?
C54 C55 1.502(7) . ?
C54 H55 0.9900 . ?
C54 H56 0.9900 . ?
C55 H91 0.9800 . ?
C55 H92 0.9800 . ?
C55 H93 0.9800 . ?
C56 C57 1.389(7) . ?
C56 C61 1.411(6) . ?
C56 H23 0.9500 . ?
C57 C58 1.385(8) . ?
C57 H24 0.9500 . ?
C58 C59 1.382(7) . ?
C58 H25 0.9500 . ?
C59 C60 1.383(7) . ?
C59 H26 0.9500 . ?
C60 C61 1.395(6) . ?
C60 H27 0.9500 . ?
C61 C62 1.467(6) . ?
C62 C65 1.404(6) . ?
C62 C63 1.416(6) . ?
C63 C64 1.393(6) . ?
C63 C67 1.490(6) . ?
C64 N6 1.379(6) . ?
C64 C68 1.435(6) . ?
N6 C65 1.338(6) . ?
N6 H28 0.8800 . ?
C65 C66 1.491(6) . ?
C66 H94 0.9800 . ?
C66 H95 0.9800 . ?
C66 H96 0.9800 . ?
C67 H97 0.9800 . ?
C67 H98 0.9800 . ?
C67 H99 0.9800 . ?
C68 O4 1.319(5) . ?
C68 C69 1.385(6) . ?
C69 C70 1.376(6) . ?
C69 H29 0.9500 . ?
C70 O3 1.322(6) . ?
C70 C71 1.434(6) . ?
C71 C72 1.384(7) . ?
C71 N7 1.393(6) . ?
C72 C73 1.422(7) . ?
C72 C75 1.478(7) . ?
C73 C74 1.384(7) . ?
C73 C77 1.483(7) . ?
C74 N7 1.336(6) . ?
C74 C76 1.492(7) . ?
N7 H30 0.8800 . ?
C75 H100 0.9800 . ?
C75 H101 0.9800 . ?
C75 H102 0.9800 . ?
C76 H103 0.9800 . ?
C76 H104 0.9800 . ?
C76 H105 0.9800 . ?
C77 C78 1.377(8) . ?
C77 C82 1.387(8) . ?
C78 C79 1.396(9) . ?
C78 H31 0.9500 . ?
C79 C80 1.346(10) . ?
C79 H32 0.9500 . ?
C80 C81 1.387(11) . ?
C80 H33 0.9500 . ?
C81 C82 1.377(9) . ?
C81 H34 0.9500 . ?
C82 H35 0.9500 . ?
C83 C84 1.363(9) . ?
C83 C88 1.375(7) . ?
C83 H36 0.9500 . ?
C84 C85 1.372(8) . ?
C84 H37 0.9500 . ?
C85 C86 1.390(7) . ?
C85 H38 0.9500 . ?
C86 N8 1.405(7) . ?
C86 C87 1.424(8) . ?
C87 C95 1.393(7) . ?
C87 C88 1.419(8) . ?
C88 N10 1.404(7) . ?
N8 C89 1.383(6) . ?
N8 C102 1.466(7) . ?
C89 C90 1.384(7) . ?
C89 C94 1.431(7) . ?
C90 C91 1.376(8) . ?
C90 H39 0.9500 . ?
C91 C92 1.383(7) . ?
C91 H40 0.9500 . ?
C92 C93 1.386(7) . ?
C92 H41 0.9500 . ?
C93 N9 1.383(6) . ?
C93 C94 1.425(7) . ?
C94 C95 1.395(7) . ?
C95 C101 1.419(7) . ?
N9 C96 1.387(6) . ?
N9 C105 1.478(6) . ?
C96 C97 1.386(7) . ?
C96 C101 1.421(7) . ?
C97 C98 1.382(7) . ?
C97 H42 0.9500 . ?
C98 C99 1.383(7) . ?
C98 H43 0.9500 . ?
C99 C100 1.405(8) . ?
C99 H44 0.9500 . ?
C100 N10 1.380(7) . ?
C100 C101 1.414(7) . ?
N10 C108 1.496(15) . ?
N10 C114 1.562(18) . ?
C102 C103 1.520(7) . ?
C102 H57 0.9900 . ?
C102 H58 0.9900 . ?
C103 C104 1.526(8) . ?
C103 H59 0.9900 . ?
C103 H60 0.9900 . ?
C104 H106 0.9800 . ?
C104 H107 0.9800 . ?
C104 H108 0.9800 . ?
C105 C106 1.530(6) . ?
C105 H61 0.9900 . ?
C105 H62 0.9900 . ?
C106 C107 1.509(7) . ?
C106 H63 0.9900 . ?
C106 H64 0.9900 . ?
C107 H109 0.9800 . ?
C107 H110 0.9800 . ?
C107 H111 0.9800 . ?
C108 C109 1.53(2) . ?
C108 H65 0.9900 . ?
C108 H66 0.9900 . ?
C109 C110 1.43(4) . ?
C109 H67 0.9900 . ?
C109 H68 0.9900 . ?
C110 H112 0.9800 . ?
C110 H113 0.9800 . ?
C110 H114 0.9800 . ?
C114 C115 1.50(3) . ?
C114 H69 0.9900 . ?
C114 H70 0.9900 . ?
C115 C116 1.65(4) . ?
C115 H71 0.9900 . ?
C115 H72 0.9900 . ?
C116 H115 0.9800 . ?
C116 H116 0.9800 . ?
C116 H117 0.9800 . ?
Cl6 C111 1.760(12) . ?
C111 Cl7 1.675(11) . ?
Cl8 C112 1.797(8) . ?
C112 Cl9 1.771(9) . ?
Cl4 C113 1.812(17) . ?
Cl5 C113 1.715(16) . ?
C119 C120 1.382(15) . ?
C120 C121 1.453(16) . ?
C121 C122 1.407(15) . ?
C122 C123 1.271(12) . ?
C123 C124 1.324(11) . ?

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
C6 C1 C2 120.7(6) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.7(7) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.2(7) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 122.6(7) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C5 117.4(5) . . ?
C1 C6 C7 122.3(5) . . ?
C5 C6 C7 120.3(5) . . ?
C10 C7 C8 107.5(4) . . ?
C10 C7 C6 126.2(5) . . ?
C8 C7 C6 126.2(5) . . ?
C9 C8 C7 106.5(5) . . ?
C9 C8 C12 126.6(5) . . ?
C7 C8 C12 126.8(5) . . ?
N1 C9 C8 108.1(4) . . ?
N1 C9 C13 120.3(4) . . ?
C8 C9 C13 131.6(5) . . ?
C10 N1 C9 109.1(4) . . ?
C10 N1 H6 125.4 . . ?
C9 N1 H6 125.4 . . ?
N1 C10 C7 108.7(5) . . ?
N1 C10 C11 120.0(5) . . ?
C7 C10 C11 131.2(5) . . ?
C10 C11 H73 109.5 . . ?
C10 C11 H74 109.5 . . ?
H73 C11 H74 109.5 . . ?
C10 C11 H75 109.5 . . ?
H73 C11 H75 109.5 . . ?
H74 C11 H75 109.5 . . ?
C8 C12 H76 109.5 . . ?
C8 C12 H77 109.5 . . ?
H76 C12 H77 109.5 . . ?
C8 C12 H78 109.5 . . ?
H76 C12 H78 109.5 . . ?
H77 C12 H78 109.5 . . ?
O2 C13 C14 120.5(4) . . ?
O2 C13 C9 117.0(4) . . ?
C14 C13 C9 122.5(5) . . ?
C13 C14 C15 121.9(5) . . ?
C13 C14 H7 119.1 . . ?
C15 C14 H7 119.1 . . ?
O1 C15 C14 120.4(4) . . ?
O1 C15 C16 116.9(4) . . ?
C14 C15 C16 122.8(4) . . ?
C15 O1 B1 122.0(4) . . ?
C13 O2 B1 122.1(4) . . ?
F2 B1 F1 110.4(4) . . ?
F2 B1 O2 109.0(4) . . ?
F1 B1 O2 108.6(4) . . ?
F2 B1 O1 108.7(4) . . ?
F1 B1 O1 107.2(4) . . ?
O2 B1 O1 112.9(4) . . ?
N2 C16 C17 107.2(4) . . ?
N2 C16 C15 120.9(4) . . ?
C17 C16 C15 131.8(4) . . ?
C16 C17 C18 107.1(4) . . ?
C16 C17 C20 125.1(4) . . ?
C18 C17 C20 127.8(4) . . ?
C19 C18 C17 106.9(4) . . ?
C19 C18 C22 126.9(4) . . ?
C17 C18 C22 125.8(4) . . ?
N2 C19 C18 108.2(4) . . ?
N2 C19 C21 121.0(4) . . ?
C18 C19 C21 130.7(4) . . ?
C19 N2 C16 110.5(4) . . ?
C19 N2 H8 124.7 . . ?
C16 N2 H8 124.7 . . ?
C17 C20 H79 109.5 . . ?
C17 C20 H80 109.5 . . ?
H79 C20 H80 109.5 . . ?
C17 C20 H81 109.5 . . ?
H79 C20 H81 109.5 . . ?
H80 C20 H81 109.5 . . ?
C19 C21 H82 109.5 . . ?
C19 C21 H83 109.5 . . ?
H82 C21 H83 109.5 . . ?
C19 C21 H84 109.5 . . ?
H82 C21 H84 109.5 . . ?
H83 C21 H84 109.5 . . ?
C23 C22 C27 117.0(4) . . ?
C23 C22 C18 121.8(4) . . ?
C27 C22 C18 120.9(4) . . ?
C24 C23 C22 121.5(5) . . ?
C24 C23 H9 119.3 . . ?
C22 C23 H9 119.3 . . ?
C23 C24 C25 120.5(5) . . ?
C23 C24 H10 119.7 . . ?
C25 C24 H10 119.7 . . ?
C26 C25 C24 119.0(5) . . ?
C26 C25 H11 120.5 . . ?
C24 C25 H11 120.5 . . ?
C25 C26 C27 121.0(5) . . ?
C25 C26 H12 119.5 . . ?
C27 C26 H12 119.5 . . ?
C26 C27 C22 120.9(5) . . ?
C26 C27 H13 119.6 . . ?
C22 C27 H13 119.6 . . ?
C29 C28 C33 119.1(7) . . ?
C29 C28 H14 120.4 . . ?
C33 C28 H14 120.4 . . ?
C28 C29 C30 124.0(6) . . ?
C28 C29 H15 118.0 . . ?
C30 C29 H15 118.0 . . ?
C29 C30 C31 118.3(6) . . ?
C29 C30 H16 120.8 . . ?
C31 C30 H16 120.8 . . ?
N5 C31 C32 119.1(5) . . ?
N5 C31 C30 122.4(6) . . ?
C32 C31 C30 118.5(6) . . ?
C46 C32 C31 119.6(6) . . ?
C46 C32 C33 120.7(6) . . ?
C31 C32 C33 119.7(5) . . ?
N3 C33 C28 122.0(6) . . ?
N3 C33 C32 117.7(5) . . ?
C28 C33 C32 120.3(7) . . ?
N3 C34 C35 122.7(6) . . ?
N3 C34 C39 118.1(6) . . ?
C35 C34 C39 119.2(5) . . ?
C34 C35 C36 118.3(5) . . ?
C34 C35 H17 120.9 . . ?
C36 C35 H17 120.9 . . ?
C37 C36 C35 123.9(6) . . ?
C37 C36 H18 118.0 . . ?
C35 C36 H18 118.0 . . ?
C46 C39 C38 119.5(5) . . ?
C46 C39 C34 119.7(5) . . ?
C38 C39 C34 120.8(5) . . ?
C41 C42 C43 123.2(6) . . ?
C41 C42 H19 118.4 . . ?
C43 C42 H19 118.4 . . ?
C44 C43 C42 119.2(5) . . ?
C44 C43 H20 120.4 . . ?
C42 C43 H20 120.4 . . ?
C43 C44 N5 122.3(5) . . ?
C43 C44 C45 118.9(5) . . ?
N5 C44 C45 118.9(5) . . ?
C46 C45 C44 119.6(5) . . ?
C46 C45 C40 119.6(5) . . ?
C44 C45 C40 120.8(5) . . ?
C45 C46 C32 120.6(5) . . ?
C45 C46 C39 120.3(5) . . ?
C32 C46 C39 119.1(5) . . ?
N5 C47 C48 109.8(5) . . ?
N5 C47 H45 109.7 . . ?
C48 C47 H45 109.7 . . ?
N5 C47 H46 109.7 . . ?
C48 C47 H46 109.7 . . ?
H45 C47 H46 108.2 . . ?
C49 C48 C47 110.9(7) . . ?
C49 C48 H47 109.5 . . ?
C47 C48 H47 109.5 . . ?
C49 C48 H48 109.5 . . ?
C47 C48 H48 109.5 . . ?
H47 C48 H48 108.0 . . ?
C48 C49 H85 109.5 . . ?
C48 C49 H86 109.5 . . ?
H85 C49 H86 109.5 . . ?
C48 C49 H87 109.5 . . ?
H85 C49 H87 109.5 . . ?
H86 C49 H87 109.5 . . ?
C51 C50 N3 104.5(7) . . ?
C51 C50 H49 110.8 . . ?
N3 C50 H49 110.8 . . ?
C51 C50 H50 110.8 . . ?
N3 C50 H50 110.8 . . ?
H49 C50 H50 108.9 . . ?
C50 C51 C52 102.0(7) . . ?
C50 C51 H51 111.4 . . ?
C52 C51 H51 111.4 . . ?
C50 C51 H52 111.4 . . ?
C52 C51 H52 111.4 . . ?
H51 C51 H52 109.2 . . ?
C51 C52 H88 109.5 . . ?
C51 C52 H89 109.5 . . ?
H88 C52 H89 109.5 . . ?
C51 C52 H90 109.5 . . ?
H88 C52 H90 109.5 . . ?
H89 C52 H90 109.5 . . ?
F4 B2 F3 111.9(4) . . ?
F4 B2 O3 108.9(4) . . ?
F3 B2 O3 108.6(4) . . ?
F4 B2 O4 108.7(4) . . ?
F3 B2 O4 108.0(4) . . ?
O3 B2 O4 110.8(4) . . ?
C33 N3 C34 124.5(6) . . ?
C33 N3 C50 116.3(5) . . ?
C34 N3 C50 118.3(6) . . ?
C36 C37 C38 119.0(5) . . ?
C36 C37 H21 120.5 . . ?
C38 C37 H21 120.5 . . ?
N4 C38 C37 122.0(5) . . ?
N4 C38 C39 119.4(5) . . ?
C37 C38 C39 118.7(5) . . ?
C38 N4 C40 122.8(4) . . ?
C38 N4 C53 118.2(4) . . ?
C40 N4 C53 119.1(4) . . ?
N4 C40 C41 122.5(5) . . ?
N4 C40 C45 118.4(5) . . ?
C41 C40 C45 119.1(5) . . ?
C42 C41 C40 118.8(5) . . ?
C42 C41 H22 120.6 . . ?
C40 C41 H22 120.6 . . ?
C31 N5 C44 122.2(5) . . ?
C31 N5 C47 117.9(5) . . ?
C44 N5 C47 119.9(5) . . ?
N4 C53 C54 111.6(4) . . ?
N4 C53 H53 109.3 . . ?
C54 C53 H53 109.3 . . ?
N4 C53 H54 109.3 . . ?
C54 C53 H54 109.3 . . ?
H53 C53 H54 108.0 . . ?
C55 C54 C53 110.4(4) . . ?
C55 C54 H55 109.6 . . ?
C53 C54 H55 109.6 . . ?
C55 C54 H56 109.6 . . ?
C53 C54 H56 109.6 . . ?
H55 C54 H56 108.1 . . ?
C54 C55 H91 109.5 . . ?
C54 C55 H92 109.5 . . ?
H91 C55 H92 109.5 . . ?
C54 C55 H93 109.5 . . ?
H91 C55 H93 109.5 . . ?
H92 C55 H93 109.5 . . ?
C57 C56 C61 120.0(5) . . ?
C57 C56 H23 120.0 . . ?
C61 C56 H23 120.0 . . ?
C58 C57 C56 121.0(5) . . ?
C58 C57 H24 119.5 . . ?
C56 C57 H24 119.5 . . ?
C59 C58 C57 119.2(5) . . ?
C59 C58 H25 120.4 . . ?
C57 C58 H25 120.4 . . ?
C58 C59 C60 120.6(5) . . ?
C58 C59 H26 119.7 . . ?
C60 C59 H26 119.7 . . ?
C59 C60 C61 121.1(5) . . ?
C59 C60 H27 119.4 . . ?
C61 C60 H27 119.4 . . ?
C60 C61 C56 118.0(4) . . ?
C60 C61 C62 121.1(4) . . ?
C56 C61 C62 120.8(4) . . ?
C65 C62 C63 106.7(4) . . ?
C65 C62 C61 125.6(4) . . ?
C63 C62 C61 127.3(4) . . ?
C64 C63 C62 107.1(4) . . ?
C64 C63 C67 126.0(4) . . ?
C62 C63 C67 126.9(4) . . ?
N6 C64 C63 107.5(4) . . ?
N6 C64 C68 121.2(4) . . ?
C63 C64 C68 131.2(4) . . ?
C65 N6 C64 110.2(4) . . ?
C65 N6 H28 124.9 . . ?
C64 N6 H28 124.9 . . ?
N6 C65 C62 108.5(4) . . ?
N6 C65 C66 121.0(4) . . ?
C62 C65 C66 130.6(4) . . ?
C65 C66 H94 109.5 . . ?
C65 C66 H95 109.5 . . ?
H94 C66 H95 109.5 . . ?
C65 C66 H96 109.5 . . ?
H94 C66 H96 109.5 . . ?
H95 C66 H96 109.5 . . ?
C63 C67 H97 109.5 . . ?
C63 C67 H98 109.5 . . ?
H97 C67 H98 109.5 . . ?
C63 C67 H99 109.5 . . ?
H97 C67 H99 109.5 . . ?
H98 C67 H99 109.5 . . ?
O4 C68 C69 120.3(4) . . ?
O4 C68 C64 117.2(4) . . ?
C69 C68 C64 122.5(4) . . ?
C70 C69 C68 120.8(5) . . ?
C70 C69 H29 119.6 . . ?
C68 C69 H29 119.6 . . ?
O3 C70 C69 120.5(4) . . ?
O3 C70 C71 116.3(4) . . ?
C69 C70 C71 123.1(4) . . ?
C70 O3 B2 119.9(4) . . ?
C68 O4 B2 119.7(4) . . ?
C72 C71 N7 108.2(4) . . ?
C72 C71 C70 131.3(5) . . ?
N7 C71 C70 120.5(4) . . ?
C71 C72 C73 106.0(4) . . ?
C71 C72 C75 127.5(4) . . ?
C73 C72 C75 126.5(4) . . ?
C74 C73 C72 107.7(4) . . ?
C74 C73 C77 126.3(5) . . ?
C72 C73 C77 125.8(5) . . ?
N7 C74 C73 108.8(4) . . ?
N7 C74 C76 121.7(5) . . ?
C73 C74 C76 129.5(4) . . ?
C74 N7 C71 109.2(4) . . ?
C74 N7 H30 125.4 . . ?
C71 N7 H30 125.4 . . ?
C72 C75 H100 109.5 . . ?
C72 C75 H101 109.5 . . ?
H100 C75 H101 109.5 . . ?
C72 C75 H102 109.5 . . ?
H100 C75 H102 109.5 . . ?
H101 C75 H102 109.5 . . ?
C74 C76 H103 109.5 . . ?
C74 C76 H104 109.5 . . ?
H103 C76 H104 109.5 . . ?
C74 C76 H105 109.5 . . ?
H103 C76 H105 109.5 . . ?
H104 C76 H105 109.5 . . ?
C78 C77 C82 118.0(6) . . ?
C78 C77 C73 121.7(5) . . ?
C82 C77 C73 120.3(5) . . ?
C77 C78 C79 119.3(7) . . ?
C77 C78 H31 120.3 . . ?
C79 C78 H31 120.3 . . ?
C80 C79 C78 122.1(7) . . ?
C80 C79 H32 119.0 . . ?
C78 C79 H32 119.0 . . ?
C79 C80 C81 119.4(7) . . ?
C79 C80 H33 120.3 . . ?
C81 C80 H33 120.3 . . ?
C82 C81 C80 119.0(8) . . ?
C82 C81 H34 120.5 . . ?
C80 C81 H34 120.5 . . ?
C81 C82 C77 122.1(7) . . ?
C81 C82 H35 118.9 . . ?
C77 C82 H35 118.9 . . ?
C84 C83 C88 119.9(6) . . ?
C84 C83 H36 120.1 . . ?
C88 C83 H36 120.1 . . ?
C83 C84 C85 123.1(5) . . ?
C83 C84 H37 118.4 . . ?
C85 C84 H37 118.4 . . ?
C84 C85 C86 118.7(6) . . ?
C84 C85 H38 120.6 . . ?
C86 C85 H38 120.6 . . ?
C85 C86 N8 121.9(5) . . ?
C85 C86 C87 119.7(5) . . ?
N8 C86 C87 118.3(5) . . ?
C95 C87 C88 121.5(5) . . ?
C95 C87 C86 119.6(5) . . ?
C88 C87 C86 118.9(5) . . ?
C83 C88 N10 122.7(5) . . ?
C83 C88 C87 119.6(5) . . ?
N10 C88 C87 117.6(5) . . ?
C89 N8 C86 122.4(4) . . ?
C89 N8 C102 118.5(5) . . ?
C86 N8 C102 119.1(4) . . ?
N8 C89 C90 122.3(5) . . ?
N8 C89 C94 118.4(5) . . ?
C90 C89 C94 119.3(5) . . ?
C91 C90 C89 119.2(5) . . ?
C91 C90 H39 120.4 . . ?
C89 C90 H39 120.4 . . ?
C90 C91 C92 123.4(5) . . ?
C90 C91 H40 118.3 . . ?
C92 C91 H40 118.3 . . ?
C91 C92 C93 119.1(5) . . ?
C91 C92 H41 120.4 . . ?
C93 C92 H41 120.4 . . ?
N9 C93 C92 122.5(4) . . ?
N9 C93 C94 118.2(4) . . ?
C92 C93 C94 119.2(4) . . ?
C95 C94 C93 120.7(4) . . ?
C95 C94 C89 119.6(4) . . ?
C93 C94 C89 119.7(4) . . ?
C87 C95 C94 121.2(5) . . ?
C87 C95 C101 119.1(5) . . ?
C94 C95 C101 119.6(4) . . ?
C93 N9 C96 122.9(4) . . ?
C93 N9 C105 117.4(4) . . ?
C96 N9 C105 119.7(4) . . ?
C97 C96 N9 122.4(4) . . ?
C97 C96 C101 118.9(4) . . ?
N9 C96 C101 118.7(4) . . ?
C98 C97 C96 119.9(5) . . ?
C98 C97 H42 120.0 . . ?
C96 C97 H42 120.0 . . ?
C97 C98 C99 122.6(5) . . ?
C97 C98 H43 118.7 . . ?
C99 C98 H43 118.7 . . ?
C98 C99 C100 118.9(5) . . ?
C98 C99 H44 120.5 . . ?
C100 C99 H44 120.5 . . ?
N10 C100 C99 121.4(5) . . ?
N10 C100 C101 119.4(5) . . ?
C99 C100 C101 119.2(5) . . ?
C100 C101 C95 119.9(5) . . ?
C100 C101 C96 120.4(5) . . ?
C95 C101 C96 119.7(4) . . ?
C100 N10 C88 122.3(4) . . ?
C100 N10 C108 117.8(6) . . ?
C88 N10 C108 115.9(6) . . ?
C100 N10 C114 116.2(7) . . ?
C88 N10 C114 117.3(6) . . ?
N8 C102 C103 113.9(4) . . ?
N8 C102 H57 108.8 . . ?
C103 C102 H57 108.8 . . ?
N8 C102 H58 108.8 . . ?
C103 C102 H58 108.8 . . ?
H57 C102 H58 107.7 . . ?
C102 C103 C104 109.4(5) . . ?
C102 C103 H59 109.8 . . ?
C104 C103 H59 109.8 . . ?
C102 C103 H60 109.8 . . ?
C104 C103 H60 109.8 . . ?
H59 C103 H60 108.2 . . ?
C103 C104 H106 109.5 . . ?
C103 C104 H107 109.5 . . ?
H106 C104 H107 109.5 . . ?
C103 C104 H108 109.5 . . ?
H106 C104 H108 109.5 . . ?
H107 C104 H108 109.5 . . ?
N9 C105 C106 111.9(4) . . ?
N9 C105 H61 109.2 . . ?
C106 C105 H61 109.2 . . ?
N9 C105 H62 109.2 . . ?
C106 C105 H62 109.2 . . ?
H61 C105 H62 107.9 . . ?
C107 C106 C105 110.4(4) . . ?
C107 C106 H63 109.6 . . ?
C105 C106 H63 109.6 . . ?
C107 C106 H64 109.6 . . ?
C105 C106 H64 109.6 . . ?
H63 C106 H64 108.1 . . ?
C106 C107 H109 109.5 . . ?
C106 C107 H110 109.5 . . ?
H109 C107 H110 109.5 . . ?
C106 C107 H111 109.5 . . ?
H109 C107 H111 109.5 . . ?
H110 C107 H111 109.5 . . ?
N10 C108 C109 109.5(10) . . ?
N10 C108 H65 109.8 . . ?
C109 C108 H65 109.8 . . ?
N10 C108 H66 109.8 . . ?
C109 C108 H66 109.8 . . ?
H65 C108 H66 108.2 . . ?
C110 C109 C108 107.2(16) . . ?
C110 C109 H67 110.3 . . ?
C108 C109 H67 110.3 . . ?
C110 C109 H68 110.3 . . ?
C108 C109 H68 110.3 . . ?
H67 C109 H68 108.5 . . ?
C109 C110 H112 109.5 . . ?
C109 C110 H113 109.5 . . ?
H112 C110 H113 109.5 . . ?
C109 C110 H114 109.5 . . ?
H112 C110 H114 109.5 . . ?
H113 C110 H114 109.5 . . ?
C115 C114 N10 106.0(12) . . ?
C115 C114 H69 110.5 . . ?
N10 C114 H69 110.5 . . ?
C115 C114 H70 110.5 . . ?
N10 C114 H70 110.5 . . ?
H69 C114 H70 108.7 . . ?
C114 C115 C116 108.7(17) . . ?
C114 C115 H71 110.0 . . ?
C116 C115 H71 110.0 . . ?
C114 C115 H72 110.0 . . ?
C116 C115 H72 110.0 . . ?
H71 C115 H72 108.3 . . ?
C115 C116 H115 109.5 . . ?
C115 C116 H116 109.5 . . ?
H115 C116 H116 109.5 . . ?
C115 C116 H117 109.5 . . ?
H115 C116 H117 109.5 . . ?
H116 C116 H117 109.5 . . ?
Cl7 C111 Cl6 112.4(7) . . ?
Cl9 C112 Cl8 110.0(5) . . ?
Cl5 C113 Cl4 107.0(9) . . ?
C119 C120 C121 125.0(16) . . ?
C122 C121 C120 114.0(14) . . ?
C123 C122 C121 137.0(18) . . ?
C122 C123 C124 171.5(15) . . ?

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 1.9(11) . . . . ?
C1 C2 C3 C4 -1.2(12) . . . . ?
C2 C3 C4 C5 0.3(12) . . . . ?
C3 C4 C5 C6 0.0(12) . . . . ?
C2 C1 C6 C5 -1.6(9) . . . . ?
C2 C1 C6 C7 177.6(6) . . . . ?
C4 C5 C6 C1 0.6(10) . . . . ?
C4 C5 C6 C7 -178.6(7) . . . . ?
C1 C6 C7 C10 -50.5(9) . . . . ?
C5 C6 C7 C10 128.7(7) . . . . ?
C1 C6 C7 C8 133.2(6) . . . . ?
C5 C6 C7 C8 -47.6(9) . . . . ?
C10 C7 C8 C9 0.3(6) . . . . ?
C6 C7 C8 C9 177.2(5) . . . . ?
C10 C7 C8 C12 176.3(5) . . . . ?
C6 C7 C8 C12 -6.8(9) . . . . ?
C7 C8 C9 N1 -0.6(5) . . . . ?
C12 C8 C9 N1 -176.6(5) . . . . ?
C7 C8 C9 C13 177.8(5) . . . . ?
C12 C8 C9 C13 1.8(9) . . . . ?
C8 C9 N1 C10 0.6(5) . . . . ?
C13 C9 N1 C10 -178.0(4) . . . . ?
C9 N1 C10 C7 -0.4(6) . . . . ?
C9 N1 C10 C11 -178.4(5) . . . . ?
C8 C7 C10 N1 0.0(6) . . . . ?
C6 C7 C10 N1 -176.8(5) . . . . ?
C8 C7 C10 C11 177.7(6) . . . . ?
C6 C7 C10 C11 0.8(10) . . . . ?
N1 C9 C13 O2 -171.1(4) . . . . ?
C8 C9 C13 O2 10.7(8) . . . . ?
N1 C9 C13 C14 9.3(7) . . . . ?
C8 C9 C13 C14 -168.9(5) . . . . ?
O2 C13 C14 C15 -0.6(8) . . . . ?
C9 C13 C14 C15 179.0(5) . . . . ?
C13 C14 C15 O1 0.7(7) . . . . ?
C13 C14 C15 C16 -179.8(4) . . . . ?
C14 C15 O1 B1 2.7(7) . . . . ?
C16 C15 O1 B1 -176.8(4) . . . . ?
C14 C13 O2 B1 -3.0(7) . . . . ?
C9 C13 O2 B1 177.4(4) . . . . ?
C13 O2 B1 F2 126.7(5) . . . . ?
C13 O2 B1 F1 -113.0(5) . . . . ?
C13 O2 B1 O1 5.8(6) . . . . ?
C15 O1 B1 F2 -126.7(4) . . . . ?
C15 O1 B1 F1 113.9(5) . . . . ?
C15 O1 B1 O2 -5.7(6) . . . . ?
O1 C15 C16 N2 175.9(4) . . . . ?
C14 C15 C16 N2 -3.6(7) . . . . ?
O1 C15 C16 C17 -8.2(7) . . . . ?
C14 C15 C16 C17 172.3(5) . . . . ?
N2 C16 C17 C18 -0.1(5) . . . . ?
C15 C16 C17 C18 -176.3(4) . . . . ?
N2 C16 C17 C20 178.4(4) . . . . ?
C15 C16 C17 C20 2.1(7) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C20 C17 C18 C19 -178.4(4) . . . . ?
C16 C17 C18 C22 172.9(4) . . . . ?
C20 C17 C18 C22 -5.6(7) . . . . ?
C17 C18 C19 N2 0.1(5) . . . . ?
C22 C18 C19 N2 -172.7(4) . . . . ?
C17 C18 C19 C21 -178.3(5) . . . . ?
C22 C18 C19 C21 8.9(8) . . . . ?
C18 C19 N2 C16 -0.1(5) . . . . ?
C21 C19 N2 C16 178.5(4) . . . . ?
C17 C16 N2 C19 0.1(5) . . . . ?
C15 C16 N2 C19 176.9(4) . . . . ?
C19 C18 C22 C23 -146.2(5) . . . . ?
C17 C18 C22 C23 42.3(7) . . . . ?
C19 C18 C22 C27 38.9(7) . . . . ?
C17 C18 C22 C27 -132.5(5) . . . . ?
C27 C22 C23 C24 1.4(7) . . . . ?
C18 C22 C23 C24 -173.6(4) . . . . ?
C22 C23 C24 C25 -0.1(8) . . . . ?
C23 C24 C25 C26 -1.9(8) . . . . ?
C24 C25 C26 C27 2.6(8) . . . . ?
C25 C26 C27 C22 -1.3(8) . . . . ?
C23 C22 C27 C26 -0.7(7) . . . . ?
C18 C22 C27 C26 174.4(5) . . . . ?
C33 C28 C29 C30 0.9(9) . . . . ?
C28 C29 C30 C31 2.0(9) . . . . ?
C29 C30 C31 N5 175.9(5) . . . . ?
C29 C30 C31 C32 -3.3(8) . . . . ?
N5 C31 C32 C46 2.0(7) . . . . ?
C30 C31 C32 C46 -178.8(5) . . . . ?
N5 C31 C32 C33 -177.5(5) . . . . ?
C30 C31 C32 C33 1.7(7) . . . . ?
C29 C28 C33 N3 179.5(6) . . . . ?
C29 C28 C33 C32 -2.6(9) . . . . ?
C46 C32 C33 N3 -0.2(8) . . . . ?
C31 C32 C33 N3 179.2(5) . . . . ?
C46 C32 C33 C28 -178.2(5) . . . . ?
C31 C32 C33 C28 1.2(8) . . . . ?
N3 C34 C35 C36 177.1(6) . . . . ?
C39 C34 C35 C36 -1.9(8) . . . . ?
C34 C35 C36 C37 -0.7(8) . . . . ?
N3 C34 C39 C46 3.9(8) . . . . ?
C35 C34 C39 C46 -177.0(5) . . . . ?
N3 C34 C39 C38 -177.1(5) . . . . ?
C35 C34 C39 C38 2.0(8) . . . . ?
C41 C42 C43 C44 -2.2(8) . . . . ?
C42 C43 C44 N5 -176.7(5) . . . . ?
C42 C43 C44 C45 2.3(8) . . . . ?
C43 C44 C45 C46 179.8(5) . . . . ?
N5 C44 C45 C46 -1.2(7) . . . . ?
C43 C44 C45 C40 0.4(7) . . . . ?
N5 C44 C45 C40 179.4(4) . . . . ?
C44 C45 C46 C32 1.6(7) . . . . ?
C40 C45 C46 C32 -179.0(4) . . . . ?
C44 C45 C46 C39 -179.5(4) . . . . ?
C40 C45 C46 C39 0.0(7) . . . . ?
C31 C32 C46 C45 -2.0(7) . . . . ?
C33 C32 C46 C45 177.4(5) . . . . ?
C31 C32 C46 C39 179.0(4) . . . . ?
C33 C32 C46 C39 -1.5(7) . . . . ?
C38 C39 C46 C45 1.7(7) . . . . ?
C34 C39 C46 C45 -179.3(5) . . . . ?
C38 C39 C46 C32 -179.3(4) . . . . ?
C34 C39 C46 C32 -0.3(7) . . . . ?
N5 C47 C48 C49 179.8(7) . . . . ?
N3 C50 C51 C52 -176.0(6) . . . . ?
C28 C33 N3 C34 -177.8(6) . . . . ?
C32 C33 N3 C34 4.2(9) . . . . ?
C28 C33 N3 C50 13.5(9) . . . . ?
C32 C33 N3 C50 -164.5(5) . . . . ?
C35 C34 N3 C33 174.9(6) . . . . ?
C39 C34 N3 C33 -6.0(9) . . . . ?
C35 C34 N3 C50 -16.7(9) . . . . ?
C39 C34 N3 C50 162.4(5) . . . . ?
C51 C50 N3 C33 -93.6(8) . . . . ?
C51 C50 N3 C34 97.0(8) . . . . ?
C35 C36 C37 C38 3.3(8) . . . . ?
C36 C37 C38 N4 177.1(4) . . . . ?
C36 C37 C38 C39 -3.2(7) . . . . ?
C46 C39 C38 N4 -0.7(7) . . . . ?
C34 C39 C38 N4 -179.7(4) . . . . ?
C46 C39 C38 C37 179.6(4) . . . . ?
C34 C39 C38 C37 0.6(7) . . . . ?
C37 C38 N4 C40 177.6(4) . . . . ?
C39 C38 N4 C40 -2.1(7) . . . . ?
C37 C38 N4 C53 -1.4(6) . . . . ?
C39 C38 N4 C53 178.9(4) . . . . ?
C38 N4 C40 C41 -176.2(4) . . . . ?
C53 N4 C40 C41 2.8(7) . . . . ?
C38 N4 C40 C45 3.8(6) . . . . ?
C53 N4 C40 C45 -177.3(4) . . . . ?
C46 C45 C40 N4 -2.6(7) . . . . ?
C44 C45 C40 N4 176.8(4) . . . . ?
C46 C45 C40 C41 177.3(4) . . . . ?
C44 C45 C40 C41 -3.3(7) . . . . ?
C43 C42 C41 C40 -0.7(8) . . . . ?
N4 C40 C41 C42 -176.7(5) . . . . ?
C45 C40 C41 C42 3.4(7) . . . . ?
C32 C31 N5 C44 -1.6(7) . . . . ?
C30 C31 N5 C44 179.2(5) . . . . ?
C32 C31 N5 C47 177.8(5) . . . . ?
C30 C31 N5 C47 -1.3(7) . . . . ?
C43 C44 N5 C31 -179.8(5) . . . . ?
C45 C44 N5 C31 1.2(7) . . . . ?
C43 C44 N5 C47 0.8(7) . . . . ?
C45 C44 N5 C47 -178.2(5) . . . . ?
C48 C47 N5 C31 87.9(7) . . . . ?
C48 C47 N5 C44 -92.7(7) . . . . ?
C38 N4 C53 C54 83.2(5) . . . . ?
C40 N4 C53 C54 -95.8(5) . . . . ?
N4 C53 C54 C55 -172.4(4) . . . . ?
C61 C56 C57 C58 0.1(8) . . . . ?
C56 C57 C58 C59 -0.9(8) . . . . ?
C57 C58 C59 C60 0.2(8) . . . . ?
C58 C59 C60 C61 1.3(8) . . . . ?
C59 C60 C61 C56 -2.0(7) . . . . ?
C59 C60 C61 C62 176.0(4) . . . . ?
C57 C56 C61 C60 1.3(7) . . . . ?
C57 C56 C61 C62 -176.7(5) . . . . ?
C60 C61 C62 C65 145.2(5) . . . . ?
C56 C61 C62 C65 -36.8(7) . . . . ?
C60 C61 C62 C63 -42.6(7) . . . . ?
C56 C61 C62 C63 135.4(5) . . . . ?
C65 C62 C63 C64 -0.5(5) . . . . ?
C61 C62 C63 C64 -173.9(4) . . . . ?
C65 C62 C63 C67 178.1(4) . . . . ?
C61 C62 C63 C67 4.8(7) . . . . ?
C62 C63 C64 N6 0.0(5) . . . . ?
C67 C63 C64 N6 -178.7(4) . . . . ?
C62 C63 C64 C68 177.5(4) . . . . ?
C67 C63 C64 C68 -1.1(8) . . . . ?
C63 C64 N6 C65 0.5(5) . . . . ?
C68 C64 N6 C65 -177.3(4) . . . . ?
C64 N6 C65 C62 -0.9(5) . . . . ?
C64 N6 C65 C66 -179.6(4) . . . . ?
C63 C62 C65 N6 0.8(5) . . . . ?
C61 C62 C65 N6 174.4(4) . . . . ?
C63 C62 C65 C66 179.4(5) . . . . ?
C61 C62 C65 C66 -7.1(8) . . . . ?
N6 C64 C68 O4 178.1(4) . . . . ?
C63 C64 C68 O4 0.9(7) . . . . ?
N6 C64 C68 C69 0.4(7) . . . . ?
C63 C64 C68 C69 -176.8(4) . . . . ?
O4 C68 C69 C70 -6.5(7) . . . . ?
C64 C68 C69 C70 171.1(4) . . . . ?
C68 C69 C70 O3 8.0(7) . . . . ?
C68 C69 C70 C71 -169.5(4) . . . . ?
C69 C70 O3 B2 11.5(6) . . . . ?
C71 C70 O3 B2 -170.9(4) . . . . ?
F4 B2 O3 C70 -148.6(4) . . . . ?
F3 B2 O3 C70 89.3(5) . . . . ?
O4 B2 O3 C70 -29.1(6) . . . . ?
C69 C68 O4 B2 -14.2(6) . . . . ?
C64 C68 O4 B2 168.1(4) . . . . ?
F4 B2 O4 C68 150.1(4) . . . . ?
F3 B2 O4 C68 -88.3(5) . . . . ?
O3 B2 O4 C68 30.5(6) . . . . ?
O3 C70 C71 C72 5.1(8) . . . . ?
C69 C70 C71 C72 -177.3(5) . . . . ?
O3 C70 C71 N7 -174.0(4) . . . . ?
C69 C70 C71 N7 3.5(7) . . . . ?
N7 C71 C72 C73 -0.9(6) . . . . ?
C70 C71 C72 C73 179.9(5) . . . . ?
N7 C71 C72 C75 177.5(5) . . . . ?
C70 C71 C72 C75 -1.7(9) . . . . ?
C71 C72 C73 C74 1.9(6) . . . . ?
C75 C72 C73 C74 -176.4(5) . . . . ?
C71 C72 C73 C77 -174.1(5) . . . . ?
C75 C72 C73 C77 7.6(9) . . . . ?
C72 C73 C74 N7 -2.3(6) . . . . ?
C77 C73 C74 N7 173.7(5) . . . . ?
C72 C73 C74 C76 178.9(6) . . . . ?
C77 C73 C74 C76 -5.1(10) . . . . ?
C73 C74 N7 C71 1.7(6) . . . . ?
C76 C74 N7 C71 -179.3(5) . . . . ?
C72 C71 N7 C74 -0.5(6) . . . . ?
C70 C71 N7 C74 178.8(4) . . . . ?
C74 C73 C77 C78 57.7(9) . . . . ?
C72 C73 C77 C78 -127.1(6) . . . . ?
C74 C73 C77 C82 -122.1(7) . . . . ?
C72 C73 C77 C82 53.2(9) . . . . ?
C82 C77 C78 C79 -3.0(9) . . . . ?
C73 C77 C78 C79 177.3(6) . . . . ?
C77 C78 C79 C80 0.3(11) . . . . ?
C78 C79 C80 C81 1.8(12) . . . . ?
C79 C80 C81 C82 -1.2(12) . . . . ?
C80 C81 C82 C77 -1.6(11) . . . . ?
C78 C77 C82 C81 3.7(10) . . . . ?
C73 C77 C82 C81 -176.6(6) . . . . ?
C88 C83 C84 C85 0.3(8) . . . . ?
C83 C84 C85 C86 -1.0(8) . . . . ?
C84 C85 C86 N8 -179.8(4) . . . . ?
C84 C85 C86 C87 0.7(7) . . . . ?
C85 C86 C87 C95 179.9(5) . . . . ?
N8 C86 C87 C95 0.4(7) . . . . ?
C85 C86 C87 C88 0.3(7) . . . . ?
N8 C86 C87 C88 -179.2(4) . . . . ?
C84 C83 C88 N10 -177.0(5) . . . . ?
C84 C83 C88 C87 0.8(8) . . . . ?
C95 C87 C88 C83 179.4(5) . . . . ?
C86 C87 C88 C83 -1.0(7) . . . . ?
C95 C87 C88 N10 -2.7(7) . . . . ?
C86 C87 C88 N10 176.9(5) . . . . ?
C85 C86 N8 C89 174.6(4) . . . . ?
C87 C86 N8 C89 -5.9(7) . . . . ?
C85 C86 N8 C102 -7.2(7) . . . . ?
C87 C86 N8 C102 172.2(4) . . . . ?
C86 N8 C89 C90 -173.6(5) . . . . ?
C102 N8 C89 C90 8.3(7) . . . . ?
C86 N8 C89 C94 7.6(6) . . . . ?
C102 N8 C89 C94 -170.6(4) . . . . ?
N8 C89 C90 C91 -177.0(5) . . . . ?
C94 C89 C90 C91 1.8(7) . . . . ?
C89 C90 C91 C92 0.6(8) . . . . ?
C90 C91 C92 C93 -2.4(7) . . . . ?
C91 C92 C93 N9 -178.6(4) . . . . ?
C91 C92 C93 C94 1.5(7) . . . . ?
N9 C93 C94 C95 1.1(6) . . . . ?
C92 C93 C94 C95 -179.0(4) . . . . ?
N9 C93 C94 C89 -179.1(4) . . . . ?
C92 C93 C94 C89 0.8(6) . . . . ?
N8 C89 C94 C95 -3.8(6) . . . . ?
C90 C89 C94 C95 177.3(4) . . . . ?
N8 C89 C94 C93 176.3(4) . . . . ?
C90 C89 C94 C93 -2.5(7) . . . . ?
C88 C87 C95 C94 -177.2(4) . . . . ?
C86 C87 C95 C94 3.2(7) . . . . ?
C88 C87 C95 C101 3.5(7) . . . . ?
C86 C87 C95 C101 -176.0(4) . . . . ?
C93 C94 C95 C87 178.3(4) . . . . ?
C89 C94 C95 C87 -1.5(7) . . . . ?
C93 C94 C95 C101 -2.4(6) . . . . ?
C89 C94 C95 C101 177.7(4) . . . . ?
C92 C93 N9 C96 -177.5(4) . . . . ?
C94 C93 N9 C96 2.4(6) . . . . ?
C92 C93 N9 C105 2.8(6) . . . . ?
C94 C93 N9 C105 -177.2(4) . . . . ?
C93 N9 C96 C97 174.9(4) . . . . ?
C105 N9 C96 C97 -5.5(7) . . . . ?
C93 N9 C96 C101 -4.3(6) . . . . ?
C105 N9 C96 C101 175.3(4) . . . . ?
N9 C96 C97 C98 178.0(4) . . . . ?
C101 C96 C97 C98 -2.8(7) . . . . ?
C96 C97 C98 C99 -0.1(8) . . . . ?
C97 C98 C99 C100 2.0(8) . . . . ?
C98 C99 C100 N10 -179.6(5) . . . . ?
C98 C99 C100 C101 -0.8(8) . . . . ?
N10 C100 C101 C95 -3.0(7) . . . . ?
C99 C100 C101 C95 178.2(5) . . . . ?
N10 C100 C101 C96 176.7(5) . . . . ?
C99 C100 C101 C96 -2.2(7) . . . . ?
C87 C95 C101 C100 -0.7(7) . . . . ?
C94 C95 C101 C100 -179.9(4) . . . . ?
C87 C95 C101 C96 179.7(4) . . . . ?
C94 C95 C101 C96 0.4(7) . . . . ?
C97 C96 C101 C100 4.0(7) . . . . ?
N9 C96 C101 C100 -176.8(4) . . . . ?
C97 C96 C101 C95 -176.4(4) . . . . ?
N9 C96 C101 C95 2.8(7) . . . . ?
C99 C100 N10 C88 -177.4(5) . . . . ?
C101 C100 N10 C88 3.9(8) . . . . ?
C99 C100 N10 C108 -20.7(9) . . . . ?
C101 C100 N10 C108 160.5(7) . . . . ?
C99 C100 N10 C114 26.2(9) . . . . ?
C101 C100 N10 C114 -152.6(7) . . . . ?
C83 C88 N10 C100 176.8(5) . . . . ?
C87 C88 N10 C100 -1.0(8) . . . . ?
C83 C88 N10 C108 19.7(9) . . . . ?
C87 C88 N10 C108 -158.1(6) . . . . ?
C83 C88 N10 C114 -27.0(9) . . . . ?
C87 C88 N10 C114 155.2(7) . . . . ?
C89 N8 C102 C103 -90.8(6) . . . . ?
C86 N8 C102 C103 91.0(6) . . . . ?
N8 C102 C103 C104 174.6(5) . . . . ?
C93 N9 C105 C106 -83.3(5) . . . . ?
C96 N9 C105 C106 97.1(5) . . . . ?
N9 C105 C106 C107 170.3(4) . . . . ?
C100 N10 C108 C109 101.7(9) . . . . ?
C88 N10 C108 C109 -100.1(10) . . . . ?
N10 C108 C109 C110 175.4(17) . . . . ?
C100 N10 C114 C115 -101.0(10) . . . . ?
C88 N10 C114 C115 101.3(10) . . . . ?
N10 C114 C115 C116 177.0(14) . . . . ?
C119 C120 C121 C122 -77(3) . . . . ?
C120 C121 C122 C123 -90(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H6 Cl1 0.88 2.45 3.297(4) 161.8 .
C14 H7 Cl1 0.95 2.61 3.557(5) 179.6 .
N2 H8 Cl1 0.88 2.48 3.351(4) 169.6 .
N1 H6 Cl1 0.88 2.45 3.297(4) 161.8 .
C14 H7 Cl1 0.95 2.61 3.557(5) 179.6 .
N6 H28 Cl2 0.88 2.46 3.313(4) 163.1 .
C69 H29 Cl2 0.95 2.64 3.535(5) 157.4 .
N7 H30 Cl2 0.88 2.43 3.306(4) 173.3 .
C50 H49 Cl1 0.99 2.96 3.929(8) 167.0 .
C50 H50 N1 0.99 2.68 3.247(9) 116.8 .
C51 H52 Cl1 0.99 2.92 3.871(9) 161.3 1_455
C53 H53 F1 0.99 2.56 3.510(6) 160.5 1_455
C102 H57 Cl2 0.99 2.98 3.876(6) 150.8 .
C102 H58 N7 0.99 2.68 3.441(7) 133.9 .
C105 H62 F3 0.99 2.49 3.430(5) 157.7 1_655
C76 H104 Cl9 0.98 2.96 3.706(7) 133.4 .

_refine_diff_density_max         1.227
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.103

