# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_compound_09
_database_code_depnum_ccdc_archive 'CCDC 1535315'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C30 H28 N2'
_chemical_formula_weight         416.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4010(6)
_cell_length_b                   9.7328(6)
_cell_length_c                   14.7598(10)
_cell_angle_alpha                71.445(2)
_cell_angle_beta                 79.849(3)
_cell_angle_gamma                86.645(3)
_cell_volume                     1126.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7165
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7101
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15427
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.476
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5177
_reflns_number_gt                4030
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0729P)²+0.1370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5177
_refine_ls_number_parameters     301
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
N01 N 0.67211(12) 0.37406(11) 0.24035(7) 0.0190(2) Uani 1 1 d D . . . .
H1N H 0.7521(18) 0.3891(17) 0.2695(11) 0.039(4) Uiso 1 1 d D . . . .
N02 N 0.41415(12) 0.23094(10) 0.36494(7) 0.0187(2) Uani 1 1 d D . . . .
H2N H 0.5109(16) 0.1999(16) 0.3407(11) 0.033(4) Uiso 1 1 d D . . . .
C01 C 0.44878(15) 0.32697(15) 0.11386(10) 0.0266(3) Uani 1 1 d . . . . .
H01A H 0.4035 0.3000 0.0651 0.040 Uiso 1 1 calc R U . . .
H01B H 0.4128 0.4250 0.1129 0.040 Uiso 1 1 calc R U . . .
H01C H 0.4117 0.2584 0.1782 0.040 Uiso 1 1 calc R U . . .
C02 C 1.01320(15) 0.36627(16) 0.18684(10) 0.0296(3) Uani 1 1 d . . . . .
H02A H 0.9893 0.4612 0.1960 0.044 Uiso 1 1 calc R U . . .
H02B H 1.1253 0.3645 0.1545 0.044 Uiso 1 1 calc R U . . .
H02C H 0.9982 0.2906 0.2500 0.044 Uiso 1 1 calc R U . . .
C03 C 0.48405(17) 0.31322(13) 0.52862(10) 0.0267(3) Uani 1 1 d . . . . .
H03A H 0.5838 0.3121 0.4830 0.040 Uiso 1 1 calc R U . . .
H03B H 0.5111 0.3102 0.5912 0.040 Uiso 1 1 calc R U . . .
H03C H 0.4230 0.4019 0.5030 0.040 Uiso 1 1 calc R U . . .
C04 C 0.23151(17) -0.01732(14) 0.39025(10) 0.0276(3) Uani 1 1 d . . . . .
H04A H 0.1598 -0.1016 0.4127 0.041 Uiso 1 1 calc R U . . .
H04B H 0.3343 -0.0409 0.3553 0.041 Uiso 1 1 calc R U . . .
H04C H 0.1804 0.0645 0.3469 0.041 Uiso 1 1 calc R U . . .
C101 C 0.40070(14) 0.38075(11) 0.32457(8) 0.0162(2) Uani 1 1 d . . . . .
C102 C 0.24920(14) 0.45587(12) 0.34085(8) 0.0166(2) Uani 1 1 d . . . . .
C103 C 0.10871(15) 0.38191(13) 0.39819(9) 0.0199(3) Uani 1 1 d . . . . .
H103 H 0.1148 0.2809 0.4307 0.024 Uiso 1 1 calc R U . . .
C104 C -0.03656(15) 0.45214(13) 0.40823(10) 0.0241(3) Uani 1 1 d . . . . .
H104 H -0.1294 0.4000 0.4476 0.029 Uiso 1 1 calc R U . . .
C105 C -0.04765(16) 0.60011(14) 0.36048(10) 0.0271(3) Uani 1 1 d . . . . .
H105 H -0.1484 0.6487 0.3666 0.033 Uiso 1 1 calc R U . . .
C106 C 0.08697(16) 0.67555(13) 0.30464(10) 0.0250(3) Uani 1 1 d . . . . .
H106 H 0.0779 0.7766 0.2731 0.030 Uiso 1 1 calc R U . . .
C107 C 0.23832(15) 0.60750(12) 0.29267(8) 0.0188(3) Uani 1 1 d . . . . .
C108 C 0.37975(15) 0.68650(12) 0.23109(8) 0.0192(3) Uani 1 1 d . . . . .
C109 C 0.38078(17) 0.83888(13) 0.18764(9) 0.0251(3) Uani 1 1 d . . . . .
H109 H 0.2857 0.8928 0.1992 0.030 Uiso 1 1 calc R U . . .
C110 C 0.51577(18) 0.91040(13) 0.12936(10) 0.0302(3) Uani 1 1 d . . . . .
H110 H 0.5138 1.0128 0.1015 0.036 Uiso 1 1 calc R U . . .
C111 C 0.65606(18) 0.83301(14) 0.11083(10) 0.0305(3) Uani 1 1 d . . . . .
H111 H 0.7493 0.8828 0.0701 0.037 Uiso 1 1 calc R U . . .
C112 C 0.65971(16) 0.68480(13) 0.15143(9) 0.0249(3) Uani 1 1 d . . . . .
H112 H 0.7556 0.6330 0.1381 0.030 Uiso 1 1 calc R U . . .
C113 C 0.52287(15) 0.60851(12) 0.21269(8) 0.0190(3) Uani 1 1 d . . . . .
C114 C 0.52819(14) 0.45433(12) 0.25859(8) 0.0169(2) Uani 1 1 d . . . . .
C201 C 0.73206(14) 0.34890(12) 0.15072(8) 0.0170(2) Uani 1 1 d . . . . .
C202 C 0.63033(15) 0.32326(12) 0.09144(9) 0.0197(3) Uani 1 1 d . . . . .
C203 C 0.70132(17) 0.28851(13) 0.00890(9) 0.0262(3) Uani 1 1 d . . . . .
H203 H 0.6335 0.2722 -0.0318 0.031 Uiso 1 1 calc R U . . .
C204 C 0.86675(18) 0.27692(16) -0.01600(10) 0.0327(3) Uani 1 1 d . . . . .
H204 H 0.9120 0.2517 -0.0723 0.039 Uiso 1 1 calc R U . . .
C205 C 0.96514(17) 0.30268(15) 0.04263(10) 0.0305(3) Uani 1 1 d . . . . .
H205 H 1.0791 0.2952 0.0261 0.037 Uiso 1 1 calc R U . . .
C206 C 0.90064(15) 0.33938(13) 0.12531(9) 0.0218(3) Uani 1 1 d . . . . .
C301 C 0.35195(13) 0.14703(11) 0.46260(8) 0.0159(2) Uani 1 1 d . . . . .
C302 C 0.38338(14) 0.18357(12) 0.54198(9) 0.0182(3) Uani 1 1 d . . . . .
C303 C 0.31891(15) 0.09721(13) 0.63511(9) 0.0223(3) Uani 1 1 d . . . . .
H303 H 0.3389 0.1214 0.6896 0.027 Uiso 1 1 calc R U . . .
C304 C 0.22637(16) -0.02311(13) 0.64940(9) 0.0249(3) Uani 1 1 d . . . . .
H304 H 0.1812 -0.0800 0.7131 0.030 Uiso 1 1 calc R U . . .
C305 C 0.20006(15) -0.06010(12) 0.56987(10) 0.0242(3) Uani 1 1 d . . . . .
H305 H 0.1381 -0.1439 0.5800 0.029 Uiso 1 1 calc R U . . .
C306 C 0.26220(14) 0.02259(12) 0.47580(9) 0.0190(3) 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
N01 C201 1.4214(15) . ?
N01 C114 1.4330(15) . ?
N02 C101 1.3947(14) . ?
N02 C301 1.4329(15) . ?
C01 C202 1.5034(17) . ?
C02 C206 1.5068(18) . ?
C03 C302 1.5014(16) . ?
C04 C306 1.5000(18) . ?
C101 C114 1.3735(16) . ?
C101 C102 1.4516(16) . ?
C102 C103 1.4097(16) . ?
C102 C107 1.4252(15) . ?
C103 C104 1.3717(17) . ?
C104 C105 1.3932(18) . ?
C105 C106 1.3714(19) . ?
C106 C107 1.4083(17) . ?
C107 C108 1.4528(17) . ?
C108 C113 1.4159(17) . ?
C108 C109 1.4161(16) . ?
C109 C110 1.3704(19) . ?
C110 C111 1.395(2) . ?
C111 C112 1.3755(18) . ?
C112 C113 1.4130(17) . ?
C113 C114 1.4383(15) . ?
C201 C206 1.4052(17) . ?
C201 C202 1.4092(17) . ?
C202 C203 1.3918(17) . ?
C203 C204 1.3810(19) . ?
C204 C205 1.382(2) . ?
C205 C206 1.3900(18) . ?
C301 C302 1.3979(17) . ?
C301 C306 1.4065(15) . ?
C302 C303 1.3946(17) . ?
C303 C304 1.3827(17) . ?
C304 C305 1.3878(19) . ?
C305 C306 1.3895(18) . ?

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
C201 N01 C114 124.72(10) . . ?
C101 N02 C301 126.19(10) . . ?
C114 C101 N02 118.34(10) . . ?
C114 C101 C102 119.74(10) . . ?
N02 C101 C102 121.41(10) . . ?
C103 C102 C107 118.54(10) . . ?
C103 C102 C101 122.00(10) . . ?
C107 C102 C101 119.34(10) . . ?
C104 C103 C102 121.67(11) . . ?
C103 C104 C105 119.84(12) . . ?
C106 C105 C104 119.99(12) . . ?
C105 C106 C107 121.90(11) . . ?
C106 C107 C102 118.07(11) . . ?
C106 C107 C108 121.89(11) . . ?
C102 C107 C108 120.02(11) . . ?
C113 C108 C109 118.18(11) . . ?
C113 C108 C107 118.98(10) . . ?
C109 C108 C107 122.83(11) . . ?
C110 C109 C108 121.54(12) . . ?
C109 C110 C111 120.08(12) . . ?
C112 C111 C110 120.13(12) . . ?
C111 C112 C113 120.97(12) . . ?
C112 C113 C108 119.10(11) . . ?
C112 C113 C114 121.19(11) . . ?
C108 C113 C114 119.69(11) . . ?
C101 C114 N01 117.93(10) . . ?
C101 C114 C113 121.74(10) . . ?
N01 C114 C113 120.24(10) . . ?
C206 C201 C202 119.71(11) . . ?
C206 C201 N01 117.23(10) . . ?
C202 C201 N01 122.90(11) . . ?
C203 C202 C201 118.35(11) . . ?
C203 C202 C01 117.96(11) . . ?
C201 C202 C01 123.66(11) . . ?
C204 C203 C202 122.39(12) . . ?
C203 C204 C205 118.67(12) . . ?
C204 C205 C206 121.30(12) . . ?
C205 C206 C201 119.57(12) . . ?
C205 C206 C02 119.21(12) . . ?
C201 C206 C02 121.21(11) . . ?
C302 C301 C306 120.99(11) . . ?
C302 C301 N02 121.78(10) . . ?
C306 C301 N02 117.20(10) . . ?
C303 C302 C301 118.78(10) . . ?
C303 C302 C03 119.88(11) . . ?
C301 C302 C03 121.34(11) . . ?
C304 C303 C302 121.01(12) . . ?
C303 C304 C305 119.45(11) . . ?
C304 C305 C306 121.51(11) . . ?
C305 C306 C301 118.21(11) . . ?
C305 C306 C04 121.11(11) . . ?
C301 C306 C04 120.66(11) . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_compound_12
_database_code_depnum_ccdc_archive 'CCDC 1535320'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C73 H54 B2 Cl2 F10 N4'
_chemical_formula_weight         1269.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.950(3)
_cell_length_b                   15.254(5)
_cell_length_c                   14.255(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.584(16)
_cell_angle_gamma                90
_cell_volume                     3032.2(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2304
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      18.46

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46574
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_av_R_equivalents  0.1672
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5491
_reflns_number_gt                2709
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0414P)²+1.8844P] 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         5491
_refine_ls_number_parameters     428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
B01 B -0.1651(3) 0.3027(3) -0.4775(3) 0.0245(10) Uani 1 1 d . . . . .
N01 N -0.08059(18) 0.25670(19) -0.50176(18) 0.0238(7) Uani 1 1 d . . . . .
N02 N -0.14138(18) 0.35530(19) -0.39846(18) 0.0243(7) Uani 1 1 d . . . . .
F402 F -0.31877(15) 0.19338(16) -0.41076(15) 0.0517(7) Uani 1 1 d . . . . .
F403 F -0.49508(15) 0.18150(19) -0.48656(17) 0.0648(8) Uani 1 1 d . . . . .
F404 F -0.54386(15) 0.27413(17) -0.64469(17) 0.0615(8) Uani 1 1 d . . . . .
F405 F -0.41206(17) 0.37742(16) -0.72556(16) 0.0584(7) Uani 1 1 d . . . . .
F406 F -0.23355(15) 0.39024(15) -0.65021(14) 0.0477(6) Uani 1 1 d . . . . .
C01 C -0.0093(3) 0.3240(3) -0.6777(3) 0.0414(11) Uani 1 1 d . . . . .
H01A H 0.0478 0.3363 -0.6383 0.062 Uiso 1 1 calc R U . . .
H01B H -0.0617 0.3627 -0.6596 0.062 Uiso 1 1 calc R U . . .
H01C H 0.0052 0.3341 -0.7437 0.062 Uiso 1 1 calc R U . . .
C02 C -0.1226(3) 0.0750(3) -0.4723(2) 0.0413(11) Uani 1 1 d . . . . .
H02A H -0.1868 0.0967 -0.4586 0.062 Uiso 1 1 calc R U . . .
H02B H -0.0768 0.0955 -0.4237 0.062 Uiso 1 1 calc R U . . .
H02C H -0.1232 0.0107 -0.4732 0.062 Uiso 1 1 calc R U . . .
C03 C -0.1419(3) 0.5277(3) -0.4790(3) 0.0494(12) Uani 1 1 d . . . . .
H03A H -0.1659 0.4940 -0.5332 0.074 Uiso 1 1 calc R U . . .
H03B H -0.0747 0.5126 -0.4656 0.074 Uiso 1 1 calc R U . . .
H03C H -0.1471 0.5905 -0.4928 0.074 Uiso 1 1 calc R U . . .
C04 C -0.2503(3) 0.3096(3) -0.2350(3) 0.0430(11) Uani 1 1 d . . . . .
H04A H -0.2001 0.3083 -0.1855 0.064 Uiso 1 1 calc R U . . .
H04B H -0.2358 0.2661 -0.2832 0.064 Uiso 1 1 calc R U . . .
H04C H -0.3124 0.2959 -0.2079 0.064 Uiso 1 1 calc R U . . .
C101 C -0.0429(2) 0.3420(2) -0.3749(2) 0.0246(9) Uani 1 1 d . . . . .
C102 C 0.0149(2) 0.3808(2) -0.3000(2) 0.0265(9) Uani 1 1 d . . . . .
C103 C -0.0193(3) 0.4436(3) -0.2352(2) 0.0347(10) Uani 1 1 d . . . . .
H103 H -0.0843 0.4620 -0.2397 0.042 Uiso 1 1 calc R U . . .
C104 C 0.0403(3) 0.4780(3) -0.1663(3) 0.0424(11) Uani 1 1 d . . . . .
H104 H 0.0162 0.5191 -0.1229 0.051 Uiso 1 1 calc R U . . .
C105 C 0.1360(3) 0.4526(3) -0.1600(3) 0.0444(11) Uani 1 1 d . . . . .
H105 H 0.1773 0.4772 -0.1129 0.053 Uiso 1 1 calc R U . . .
C106 C 0.1706(3) 0.3924(3) -0.2212(3) 0.0383(10) Uani 1 1 d . . . . .
H106 H 0.2363 0.3763 -0.2162 0.046 Uiso 1 1 calc R U . . .
C107 C 0.1120(2) 0.3534(2) -0.2918(2) 0.0276(9) Uani 1 1 d . . . . .
C108 C 0.1495(2) 0.2876(2) -0.3548(2) 0.0271(9) Uani 1 1 d . . . . .
C109 C 0.2447(3) 0.2561(3) -0.3437(3) 0.0366(10) Uani 1 1 d . . . . .
H109 H 0.2844 0.2788 -0.2942 0.044 Uiso 1 1 calc R U . . .
C110 C 0.2810(3) 0.1941(3) -0.4022(3) 0.0408(11) Uani 1 1 d . . . . .
H110 H 0.3453 0.1748 -0.3931 0.049 Uiso 1 1 calc R U . . .
C111 C 0.2242(2) 0.1592(3) -0.4749(2) 0.0344(10) Uani 1 1 d . . . . .
H111 H 0.2496 0.1163 -0.5156 0.041 Uiso 1 1 calc R U . . .
C112 C 0.1311(2) 0.1874(2) -0.4873(2) 0.0296(9) Uani 1 1 d . . . . .
H112 H 0.0929 0.1636 -0.5373 0.036 Uiso 1 1 calc R U . . .
C113 C 0.0904(2) 0.2506(2) -0.4281(2) 0.0229(8) Uani 1 1 d . . . . .
C114 C -0.0065(2) 0.2815(2) -0.4360(2) 0.0247(9) Uani 1 1 d . . . . .
C201 C -0.0707(2) 0.1971(2) -0.5794(2) 0.0222(8) Uani 1 1 d . . . . .
C202 C -0.0389(2) 0.2297(2) -0.6647(2) 0.0249(9) Uani 1 1 d . . . . .
C203 C -0.0314(2) 0.1699(3) -0.7384(2) 0.0331(10) Uani 1 1 d . . . . .
H203 H -0.0101 0.1899 -0.7974 0.040 Uiso 1 1 calc R U . . .
C204 C -0.0545(3) 0.0822(3) -0.7274(3) 0.0374(10) Uani 1 1 d . . . . .
H204 H -0.0489 0.0428 -0.7785 0.045 Uiso 1 1 calc R U . . .
C205 C -0.0855(2) 0.0523(3) -0.6420(3) 0.0344(10) Uani 1 1 d . . . . .
H205 H -0.1016 -0.0078 -0.6350 0.041 Uiso 1 1 calc R U . . .
C206 C -0.0934(2) 0.1087(3) -0.5662(2) 0.0266(9) Uani 1 1 d . . . . .
C301 C -0.2007(2) 0.4211(2) -0.3569(2) 0.0263(9) Uani 1 1 d . . . . .
C302 C -0.2006(2) 0.5063(3) -0.3948(3) 0.0332(10) Uani 1 1 d . . . . .
C303 C -0.2540(3) 0.5712(3) -0.3506(3) 0.0423(11) Uani 1 1 d . . . . .
H303 H -0.2539 0.6294 -0.3741 0.051 Uiso 1 1 calc R U . . .
C304 C -0.3068(3) 0.5509(3) -0.2728(3) 0.0440(11) Uani 1 1 d . . . . .
H304 H -0.3428 0.5952 -0.2428 0.053 Uiso 1 1 calc R U . . .
C305 C -0.3072(3) 0.4661(3) -0.2388(3) 0.0371(10) Uani 1 1 d . . . . .
H305 H -0.3451 0.4528 -0.1863 0.045 Uiso 1 1 calc R U . . .
C306 C -0.2543(2) 0.3997(3) -0.2786(2) 0.0292(9) Uani 1 1 d . . . . .
C401 C -0.2684(2) 0.2932(2) -0.5265(2) 0.0262(9) Uani 1 1 d . . . . .
C402 C -0.3387(3) 0.2416(3) -0.4891(2) 0.0330(10) Uani 1 1 d . . . . .
C403 C -0.4304(3) 0.2339(3) -0.5270(3) 0.0381(10) Uani 1 1 d . . . . .
C404 C -0.4547(3) 0.2797(3) -0.6067(3) 0.0412(11) Uani 1 1 d . . . . .
C405 C -0.3880(3) 0.3319(3) -0.6474(3) 0.0370(10) Uani 1 1 d . . . . .
C406 C -0.2969(3) 0.3375(3) -0.6075(3) 0.0327(10) Uani 1 1 d . . . . .
Cl2 Cl -0.1073(2) 0.0851(2) -0.96414(17) 0.0831(10) Uani 0.5 1 d . . P A -1
Cl1 Cl 0.0550(4) -0.0272(5) -0.9965(6) 0.089(3) Uani 0.5 1 d . . P A -1
C1 C -0.0554(19) 0.008(2) -1.035(2) 0.119(15) Uani 0.5 1 d . . P A -1
H1A H -0.0987 -0.0432 -1.0411 0.142 Uiso 0.5 1 calc R U P A -1
H1B H -0.0493 0.0334 -1.0990 0.142 Uiso 0.5 1 calc R U P A -1


_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
B01 N02 1.416(5) . ?
B01 N01 1.423(5) . ?
B01 C401 1.590(5) . ?
N01 C114 1.427(4) . ?
N01 C201 1.441(4) . ?
N02 C101 1.419(4) . ?
N02 C301 1.439(4) . ?
F402 C402 1.359(4) . ?
F403 C403 1.346(4) . ?
F404 C404 1.346(4) . ?
F405 C405 1.347(4) . ?
F406 C406 1.353(4) . ?
C01 C202 1.509(5) . ?
C02 C206 1.501(5) . ?
C03 C302 1.507(5) . ?
C04 C306 1.509(5) . ?
C101 C114 1.376(5) . ?
C101 C102 1.448(5) . ?
C102 C107 1.419(5) . ?
C102 C103 1.422(5) . ?
C103 C104 1.374(5) . ?
C104 C105 1.390(5) . ?
C105 C106 1.364(5) . ?
C106 C107 1.411(5) . ?
C107 C108 1.454(5) . ?
C108 C109 1.416(5) . ?
C108 C113 1.428(5) . ?
C109 C110 1.368(5) . ?
C110 C111 1.394(5) . ?
C111 C112 1.375(5) . ?
C112 C113 1.411(5) . ?
C113 C114 1.433(5) . ?
C201 C202 1.397(5) . ?
C201 C206 1.399(5) . ?
C202 C203 1.397(5) . ?
C203 C204 1.386(5) . ?
C204 C205 1.380(5) . ?
C205 C206 1.389(5) . ?
C301 C306 1.398(5) . ?
C301 C302 1.408(5) . ?
C302 C303 1.398(5) . ?
C303 C304 1.384(5) . ?
C304 C305 1.382(5) . ?
C305 C306 1.383(5) . ?
C401 C402 1.376(5) . ?
C401 C406 1.387(5) . ?
C402 C403 1.380(5) . ?
C403 C404 1.369(5) . ?
C404 C405 1.366(5) . ?
C405 C406 1.381(5) . ?
Cl2 C1 1.73(3) . ?
Cl1 C1 1.71(2) . ?

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
N02 B01 N01 107.2(3) . . ?
N02 B01 C401 126.2(3) . . ?
N01 B01 C401 126.6(3) . . ?
B01 N01 C114 107.5(3) . . ?
B01 N01 C201 126.5(3) . . ?
C114 N01 C201 126.0(3) . . ?
B01 N02 C101 108.1(3) . . ?
B01 N02 C301 126.8(3) . . ?
C101 N02 C301 124.5(3) . . ?
C114 C101 N02 108.6(3) . . ?
C114 C101 C102 122.2(3) . . ?
N02 C101 C102 129.2(3) . . ?
C107 C102 C103 118.8(3) . . ?
C107 C102 C101 116.8(3) . . ?
C103 C102 C101 124.3(3) . . ?
C104 C103 C102 120.9(4) . . ?
C103 C104 C105 120.1(4) . . ?
C106 C105 C104 120.2(4) . . ?
C105 C106 C107 122.1(4) . . ?
C106 C107 C102 117.8(3) . . ?
C106 C107 C108 121.4(3) . . ?
C102 C107 C108 120.8(3) . . ?
C109 C108 C113 117.9(3) . . ?
C109 C108 C107 121.1(3) . . ?
C113 C108 C107 121.0(3) . . ?
C110 C109 C108 121.8(3) . . ?
C109 C110 C111 120.4(3) . . ?
C112 C111 C110 119.4(4) . . ?
C111 C112 C113 122.1(3) . . ?
C112 C113 C108 118.3(3) . . ?
C112 C113 C114 124.9(3) . . ?
C108 C113 C114 116.8(3) . . ?
C101 C114 N01 108.6(3) . . ?
C101 C114 C113 122.4(3) . . ?
N01 C114 C113 129.0(3) . . ?
C202 C201 C206 122.5(3) . . ?
C202 C201 N01 118.9(3) . . ?
C206 C201 N01 118.5(3) . . ?
C201 C202 C203 117.1(3) . . ?
C201 C202 C01 122.7(3) . . ?
C203 C202 C01 120.2(3) . . ?
C204 C203 C202 121.4(3) . . ?
C205 C204 C203 119.9(4) . . ?
C204 C205 C206 121.0(4) . . ?
C205 C206 C201 118.0(3) . . ?
C205 C206 C02 120.7(4) . . ?
C201 C206 C02 121.2(3) . . ?
C306 C301 C302 121.8(3) . . ?
C306 C301 N02 119.5(3) . . ?
C302 C301 N02 118.6(3) . . ?
C303 C302 C301 118.3(3) . . ?
C303 C302 C03 120.9(4) . . ?
C301 C302 C03 120.8(3) . . ?
C304 C303 C302 120.3(4) . . ?
C305 C304 C303 119.9(4) . . ?
C304 C305 C306 122.3(4) . . ?
C305 C306 C301 117.4(4) . . ?
C305 C306 C04 120.7(3) . . ?
C301 C306 C04 121.8(3) . . ?
C402 C401 C406 114.2(3) . . ?
C402 C401 B01 121.9(3) . . ?
C406 C401 B01 123.9(3) . . ?
F402 C402 C401 119.7(3) . . ?
F402 C402 C403 116.2(3) . . ?
C401 C402 C403 124.1(4) . . ?
F403 C403 C404 120.3(3) . . ?
F403 C403 C402 120.6(4) . . ?
C404 C403 C402 119.1(4) . . ?
F404 C404 C405 119.9(4) . . ?
F404 C404 C403 120.4(4) . . ?
C405 C404 C403 119.7(3) . . ?
F405 C405 C404 119.7(3) . . ?
F405 C405 C406 120.9(4) . . ?
C404 C405 C406 119.4(4) . . ?
F406 C406 C405 117.2(3) . . ?
F406 C406 C401 119.2(3) . . ?
C405 C406 C401 123.6(4) . . ?
Cl1 C1 Cl2 114.3(16) . . ?

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
N02 B01 N01 C114 0.6(4) . . . . ?
C401 B01 N01 C114 -176.5(3) . . . . ?
N02 B01 N01 C201 -178.4(3) . . . . ?
C401 B01 N01 C201 4.5(6) . . . . ?
N01 B01 N02 C101 0.3(4) . . . . ?
C401 B01 N02 C101 177.5(3) . . . . ?
N01 B01 N02 C301 171.6(3) . . . . ?
C401 B01 N02 C301 -11.3(6) . . . . ?
B01 N02 C101 C114 -1.2(4) . . . . ?
C301 N02 C101 C114 -172.7(3) . . . . ?
B01 N02 C101 C102 179.9(4) . . . . ?
C301 N02 C101 C102 8.4(6) . . . . ?
C114 C101 C102 C107 -0.3(5) . . . . ?
N02 C101 C102 C107 178.5(3) . . . . ?
C114 C101 C102 C103 179.9(3) . . . . ?
N02 C101 C102 C103 -1.3(6) . . . . ?
C107 C102 C103 C104 0.6(5) . . . . ?
C101 C102 C103 C104 -179.5(4) . . . . ?
C102 C103 C104 C105 1.0(6) . . . . ?
C103 C104 C105 C106 -1.1(6) . . . . ?
C104 C105 C106 C107 -0.6(6) . . . . ?
C105 C106 C107 C102 2.2(6) . . . . ?
C105 C106 C107 C108 -178.2(4) . . . . ?
C103 C102 C107 C106 -2.1(5) . . . . ?
C101 C102 C107 C106 178.0(3) . . . . ?
C103 C102 C107 C108 178.3(3) . . . . ?
C101 C102 C107 C108 -1.6(5) . . . . ?
C106 C107 C108 C109 4.1(5) . . . . ?
C102 C107 C108 C109 -176.3(3) . . . . ?
C106 C107 C108 C113 -177.9(3) . . . . ?
C102 C107 C108 C113 1.7(5) . . . . ?
C113 C108 C109 C110 1.8(5) . . . . ?
C107 C108 C109 C110 179.9(3) . . . . ?
C108 C109 C110 C111 -0.5(6) . . . . ?
C109 C110 C111 C112 -0.2(6) . . . . ?
C110 C111 C112 C113 -0.4(6) . . . . ?
C111 C112 C113 C108 1.7(5) . . . . ?
C111 C112 C113 C114 -178.8(3) . . . . ?
C109 C108 C113 C112 -2.4(5) . . . . ?
C107 C108 C113 C112 179.6(3) . . . . ?
C109 C108 C113 C114 178.2(3) . . . . ?
C107 C108 C113 C114 0.1(5) . . . . ?
N02 C101 C114 N01 1.6(4) . . . . ?
C102 C101 C114 N01 -179.4(3) . . . . ?
N02 C101 C114 C113 -176.9(3) . . . . ?
C102 C101 C114 C113 2.1(5) . . . . ?
B01 N01 C114 C101 -1.3(4) . . . . ?
C201 N01 C114 C101 177.6(3) . . . . ?
B01 N01 C114 C113 177.0(3) . . . . ?
C201 N01 C114 C113 -4.0(5) . . . . ?
C112 C113 C114 C101 178.6(3) . . . . ?
C108 C113 C114 C101 -2.0(5) . . . . ?
C112 C113 C114 N01 0.4(6) . . . . ?
C108 C113 C114 N01 179.9(3) . . . . ?
B01 N01 C201 C202 92.8(4) . . . . ?
C114 N01 C201 C202 -86.0(4) . . . . ?
B01 N01 C201 C206 -87.2(4) . . . . ?
C114 N01 C201 C206 94.0(4) . . . . ?
C206 C201 C202 C203 0.7(5) . . . . ?
N01 C201 C202 C203 -179.2(3) . . . . ?
C206 C201 C202 C01 -176.7(3) . . . . ?
N01 C201 C202 C01 3.3(5) . . . . ?
C201 C202 C203 C204 -0.1(5) . . . . ?
C01 C202 C203 C204 177.4(3) . . . . ?
C202 C203 C204 C205 -0.1(5) . . . . ?
C203 C204 C205 C206 -0.4(5) . . . . ?
C204 C205 C206 C201 1.1(5) . . . . ?
C204 C205 C206 C02 -177.0(3) . . . . ?
C202 C201 C206 C205 -1.2(5) . . . . ?
N01 C201 C206 C205 178.7(3) . . . . ?
C202 C201 C206 C02 176.8(3) . . . . ?
N01 C201 C206 C02 -3.2(4) . . . . ?
B01 N02 C301 C306 97.4(4) . . . . ?
C101 N02 C301 C306 -92.8(4) . . . . ?
B01 N02 C301 C302 -84.6(4) . . . . ?
C101 N02 C301 C302 85.3(4) . . . . ?
C306 C301 C302 C303 1.8(5) . . . . ?
N02 C301 C302 C303 -176.2(3) . . . . ?
C306 C301 C302 C03 179.8(3) . . . . ?
N02 C301 C302 C03 1.8(5) . . . . ?
C301 C302 C303 C304 -1.3(5) . . . . ?
C03 C302 C303 C304 -179.4(3) . . . . ?
C302 C303 C304 C305 -0.2(6) . . . . ?
C303 C304 C305 C306 1.5(6) . . . . ?
C304 C305 C306 C301 -1.1(5) . . . . ?
C304 C305 C306 C04 175.1(3) . . . . ?
C302 C301 C306 C305 -0.5(5) . . . . ?
N02 C301 C306 C305 177.4(3) . . . . ?
C302 C301 C306 C04 -176.7(3) . . . . ?
N02 C301 C306 C04 1.3(5) . . . . ?
N02 B01 C401 C402 -78.0(5) . . . . ?
N01 B01 C401 C402 98.6(4) . . . . ?
N02 B01 C401 C406 99.7(4) . . . . ?
N01 B01 C401 C406 -83.7(5) . . . . ?
C406 C401 C402 F402 178.5(3) . . . . ?
B01 C401 C402 F402 -3.6(5) . . . . ?
C406 C401 C402 C403 -0.4(5) . . . . ?
B01 C401 C402 C403 177.5(4) . . . . ?
F402 C402 C403 F403 0.5(5) . . . . ?
C401 C402 C403 F403 179.5(3) . . . . ?
F402 C402 C403 C404 -179.0(3) . . . . ?
C401 C402 C403 C404 0.0(6) . . . . ?
F403 C403 C404 F404 1.2(6) . . . . ?
C402 C403 C404 F404 -179.3(3) . . . . ?
F403 C403 C404 C405 -179.4(3) . . . . ?
C402 C403 C404 C405 0.1(6) . . . . ?
F404 C404 C405 F405 -0.1(6) . . . . ?
C403 C404 C405 F405 -179.6(3) . . . . ?
F404 C404 C405 C406 179.6(3) . . . . ?
C403 C404 C405 C406 0.2(6) . . . . ?
F405 C405 C406 F406 -0.1(5) . . . . ?
C404 C405 C406 F406 -179.8(3) . . . . ?
F405 C405 C406 C401 179.1(3) . . . . ?
C404 C405 C406 C401 -0.7(6) . . . . ?
C402 C401 C406 F406 179.9(3) . . . . ?
B01 C401 C406 F406 2.0(5) . . . . ?
C402 C401 C406 C405 0.8(5) . . . . ?
B01 C401 C406 C405 -177.1(4) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_compound_05
_database_code_depnum_ccdc_archive 'CCDC 1535313'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C28 H17 B F5 N O'
_chemical_formula_weight         489.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.5655(18)
_cell_length_b                   10.2491(16)
_cell_length_c                   17.699(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.760(5)
_cell_angle_gamma                90
_cell_volume                     2246.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2016
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19715
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.848
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5166
_reflns_number_gt                2774
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0700P)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         5166
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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
F304 F 0.14007(12) 0.71055(16) 0.06997(8) 0.0381(4) Uani 1 1 d . . . . .
F305 F 0.27330(13) 0.49963(15) 0.07834(8) 0.0388(4) Uani 1 1 d . . . . .
F306 F 0.43978(12) 0.47725(15) 0.19481(8) 0.0357(4) Uani 1 1 d . . . . .
F302 F 0.33923(12) 0.87541(15) 0.29694(8) 0.0352(4) Uani 1 1 d . . . . .
F303 F 0.17364(12) 0.89569(16) 0.17997(9) 0.0413(4) Uani 1 1 d . . . . .
O1 O 0.52023(13) 0.55802(17) 0.36286(9) 0.0252(4) Uani 1 1 d . . . . .
N1 N 0.58357(15) 0.7562(2) 0.33129(10) 0.0218(5) Uani 1 1 d . . . . .
C204 C 0.5882(2) 1.1126(3) 0.21669(18) 0.0478(9) Uani 1 1 d . . . . .
H204 H 0.5853 1.1924 0.1891 0.057 Uiso 1 1 calc R U . . .
C203 C 0.6150(2) 0.9999(3) 0.18343(16) 0.0414(8) Uani 1 1 d . . . . .
H203 H 0.6323 1.0033 0.1332 0.050 Uiso 1 1 calc R U . . .
C202 C 0.6178(2) 0.8807(3) 0.22052(14) 0.0311(7) Uani 1 1 d . . . . .
C201 C 0.59076(19) 0.8800(3) 0.29429(13) 0.0238(6) Uani 1 1 d . . . . .
C114 C 0.65994(19) 0.7000(2) 0.39047(12) 0.0204(6) Uani 1 1 d . . . . .
C101 C 0.61889(19) 0.5835(2) 0.40821(13) 0.0218(6) Uani 1 1 d . . . . .
C102 C 0.6699(2) 0.4970(2) 0.46530(13) 0.0232(6) Uani 1 1 d . . . . .
C107 C 0.77375(19) 0.5353(3) 0.50448(13) 0.0223(6) Uani 1 1 d . . . . .
C106 C 0.8250(2) 0.4503(3) 0.56212(14) 0.0296(6) Uani 1 1 d . . . . .
H106 H 0.8939 0.4732 0.5900 0.035 Uiso 1 1 calc R U . . .
C105 C 0.7783(2) 0.3360(3) 0.57883(15) 0.0348(7) Uani 1 1 d . . . . .
H105 H 0.8153 0.2808 0.6178 0.042 Uiso 1 1 calc R U . . .
C304 C 0.2231(2) 0.6985(3) 0.12840(13) 0.0257(6) Uani 1 1 d . . . . .
C305 C 0.2904(2) 0.5919(3) 0.13259(13) 0.0262(6) Uani 1 1 d . . . . .
C306 C 0.3748(2) 0.5824(3) 0.19292(13) 0.0242(6) Uani 1 1 d . . . . .
C301 C 0.39670(19) 0.6761(3) 0.25032(13) 0.0233(6) Uani 1 1 d . . . . .
C302 C 0.3263(2) 0.7805(2) 0.24316(13) 0.0247(6) Uani 1 1 d . . . . .
C303 C 0.2401(2) 0.7936(3) 0.18352(14) 0.0273(6) Uani 1 1 d . . . . .
C205 C 0.5651(2) 1.1109(3) 0.29091(17) 0.0397(8) Uani 1 1 d . . . . .
H205 H 0.5477 1.1898 0.3142 0.048 Uiso 1 1 calc R U . . .
C206 C 0.5675(2) 0.9941(3) 0.33092(14) 0.0261(6) Uani 1 1 d . . . . .
C2 C 0.5462(2) 0.9912(3) 0.41224(14) 0.0341(7) Uani 1 1 d . . . . .
H2A H 0.4825 0.9372 0.4148 0.051 Uiso 1 1 calc R U . . .
H2B H 0.5333 1.0801 0.4289 0.051 Uiso 1 1 calc R U . . .
H2C H 0.6089 0.9543 0.4459 0.051 Uiso 1 1 calc R U . . .
C1 C 0.6488(2) 0.7573(3) 0.18382(15) 0.0433(8) Uani 1 1 d . . . . .
H1A H 0.5840 0.7047 0.1669 0.065 Uiso 1 1 calc R U . . .
H1B H 0.6997 0.7076 0.2211 0.065 Uiso 1 1 calc R U . . .
H1C H 0.6828 0.7791 0.1396 0.065 Uiso 1 1 calc R U . . .
C113 C 0.76528(19) 0.7418(2) 0.42633(12) 0.0205(6) Uani 1 1 d . . . . .
C108 C 0.82244(19) 0.6555(2) 0.48303(12) 0.0211(6) Uani 1 1 d . . . . .
C103 C 0.6230(2) 0.3790(3) 0.48344(14) 0.0299(6) Uani 1 1 d . . . . .
H103 H 0.5538 0.3544 0.4568 0.036 Uiso 1 1 calc R U . . .
C104 C 0.6769(2) 0.2989(3) 0.53956(15) 0.0342(7) Uani 1 1 d . . . . .
H104 H 0.6453 0.2189 0.5515 0.041 Uiso 1 1 calc R U . . .
C109 C 0.9298(2) 0.6898(3) 0.51435(14) 0.0278(6) Uani 1 1 d . . . . .
H109 H 0.9698 0.6345 0.5519 0.033 Uiso 1 1 calc R U . . .
C110 C 0.9781(2) 0.8000(3) 0.49236(14) 0.0308(7) Uani 1 1 d . . . . .
H110 H 1.0508 0.8195 0.5141 0.037 Uiso 1 1 calc R U . . .
C111 C 0.9206(2) 0.8836(3) 0.43804(14) 0.0281(6) Uani 1 1 d . . . . .
H111 H 0.9542 0.9602 0.4231 0.034 Uiso 1 1 calc R U . . .
C112 C 0.8161(2) 0.8558(2) 0.40618(13) 0.0241(6) Uani 1 1 d . . . . .
H112 H 0.7773 0.9143 0.3699 0.029 Uiso 1 1 calc R U . . .
B1 B 0.4985(2) 0.6646(3) 0.31481(15) 0.0234(7) 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
F304 C304 1.345(3) . ?
F305 C305 1.339(3) . ?
F306 C306 1.349(3) . ?
F302 C302 1.351(3) . ?
F303 C303 1.334(3) . ?
O1 B1 1.383(3) . ?
O1 C101 1.383(3) . ?
N1 B1 1.416(3) . ?
N1 C114 1.417(3) . ?
N1 C201 1.438(3) . ?
C204 C203 1.365(4) . ?
C204 C205 1.393(4) . ?
C204 H204 0.9500 . ?
C203 C202 1.384(4) . ?
C203 H203 0.9500 . ?
C202 C201 1.404(3) . ?
C202 C1 1.503(4) . ?
C201 C206 1.392(4) . ?
C114 C101 1.359(3) . ?
C114 C113 1.433(3) . ?
C101 C102 1.413(3) . ?
C102 C103 1.406(4) . ?
C102 C107 1.425(3) . ?
C107 C106 1.411(3) . ?
C107 C108 1.455(4) . ?
C106 C105 1.365(4) . ?
C106 H106 0.9500 . ?
C105 C104 1.397(4) . ?
C105 H105 0.9500 . ?
C304 C303 1.370(4) . ?
C304 C305 1.375(4) . ?
C305 C306 1.375(3) . ?
C306 C301 1.391(3) . ?
C301 C302 1.380(3) . ?
C301 B1 1.568(4) . ?
C302 C303 1.385(3) . ?
C205 C206 1.388(4) . ?
C205 H205 0.9500 . ?
C206 C2 1.508(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C113 C112 1.406(3) . ?
C113 C108 1.435(3) . ?
C108 C109 1.413(3) . ?
C103 C104 1.375(3) . ?
C103 H103 0.9500 . ?
C104 H104 0.9500 . ?
C109 C110 1.369(4) . ?
C109 H109 0.9500 . ?
C110 C111 1.395(4) . ?
C110 H110 0.9500 . ?
C111 C112 1.369(3) . ?
C111 H111 0.9500 . ?
C112 H112 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C101 105.79(19) . . ?
B1 N1 C114 106.0(2) . . ?
B1 N1 C201 126.54(19) . . ?
C114 N1 C201 127.45(19) . . ?
C203 C204 C205 120.2(3) . . ?
C203 C204 H204 119.9 . . ?
C205 C204 H204 119.9 . . ?
C204 C203 C202 122.1(3) . . ?
C204 C203 H203 119.0 . . ?
C202 C203 H203 119.0 . . ?
C203 C202 C201 117.1(3) . . ?
C203 C202 C1 121.7(3) . . ?
C201 C202 C1 121.2(2) . . ?
C206 C201 C202 122.1(2) . . ?
C206 C201 N1 119.7(2) . . ?
C202 C201 N1 118.2(2) . . ?
C101 C114 N1 107.0(2) . . ?
C101 C114 C113 121.2(2) . . ?
N1 C114 C113 131.7(2) . . ?
C114 C101 O1 111.7(2) . . ?
C114 C101 C102 124.9(2) . . ?
O1 C101 C102 123.3(2) . . ?
C103 C102 C101 123.1(2) . . ?
C103 C102 C107 120.7(2) . . ?
C101 C102 C107 116.2(2) . . ?
C106 C107 C102 116.7(2) . . ?
C106 C107 C108 123.4(2) . . ?
C102 C107 C108 119.8(2) . . ?
C105 C106 C107 121.7(2) . . ?
C105 C106 H106 119.1 . . ?
C107 C106 H106 119.1 . . ?
C106 C105 C104 121.0(2) . . ?
C106 C105 H105 119.5 . . ?
C104 C105 H105 119.5 . . ?
F304 C304 C303 119.3(2) . . ?
F304 C304 C305 120.3(2) . . ?
C303 C304 C305 120.4(2) . . ?
F305 C305 C306 121.0(2) . . ?
F305 C305 C304 120.0(2) . . ?
C306 C305 C304 119.0(2) . . ?
F306 C306 C305 117.4(2) . . ?
F306 C306 C301 119.3(2) . . ?
C305 C306 C301 123.3(2) . . ?
C302 C301 C306 115.1(2) . . ?
C302 C301 B1 123.8(2) . . ?
C306 C301 B1 121.0(2) . . ?
F302 C302 C301 119.7(2) . . ?
F302 C302 C303 116.9(2) . . ?
C301 C302 C303 123.4(2) . . ?
F303 C303 C304 120.3(2) . . ?
F303 C303 C302 121.0(2) . . ?
C304 C303 C302 118.8(2) . . ?
C206 C205 C204 120.1(3) . . ?
C206 C205 H205 119.9 . . ?
C204 C205 H205 119.9 . . ?
C205 C206 C201 118.4(2) . . ?
C205 C206 C2 120.8(3) . . ?
C201 C206 C2 120.9(2) . . ?
C206 C2 H2A 109.5 . . ?
C206 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C206 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C202 C1 H1A 109.5 . . ?
C202 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C202 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C112 C113 C114 124.1(2) . . ?
C112 C113 C108 119.6(2) . . ?
C114 C113 C108 116.2(2) . . ?
C109 C108 C113 116.9(2) . . ?
C109 C108 C107 121.6(2) . . ?
C113 C108 C107 121.4(2) . . ?
C104 C103 C102 120.3(2) . . ?
C104 C103 H103 119.8 . . ?
C102 C103 H103 119.8 . . ?
C103 C104 C105 119.5(3) . . ?
C103 C104 H104 120.3 . . ?
C105 C104 H104 120.3 . . ?
C110 C109 C108 122.2(2) . . ?
C110 C109 H109 118.9 . . ?
C108 C109 H109 118.9 . . ?
C109 C110 C111 120.0(2) . . ?
C109 C110 H110 120.0 . . ?
C111 C110 H110 120.0 . . ?
C112 C111 C110 120.3(3) . . ?
C112 C111 H111 119.8 . . ?
C110 C111 H111 119.8 . . ?
C111 C112 C113 120.9(2) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.5 . . ?
O1 B1 N1 109.5(2) . . ?
O1 B1 C301 124.0(2) . . ?
N1 B1 C301 126.4(2) . . ?

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
C205 C204 C203 C202 1.6(4) . . . . ?
C204 C203 C202 C201 0.6(4) . . . . ?
C204 C203 C202 C1 -179.2(3) . . . . ?
C203 C202 C201 C206 -3.3(3) . . . . ?
C1 C202 C201 C206 176.5(2) . . . . ?
C203 C202 C201 N1 174.5(2) . . . . ?
C1 C202 C201 N1 -5.7(3) . . . . ?
B1 N1 C201 C206 102.3(3) . . . . ?
C114 N1 C201 C206 -78.7(3) . . . . ?
B1 N1 C201 C202 -75.6(3) . . . . ?
C114 N1 C201 C202 103.4(3) . . . . ?
B1 N1 C114 C101 -1.5(3) . . . . ?
C201 N1 C114 C101 179.3(2) . . . . ?
B1 N1 C114 C113 174.4(3) . . . . ?
C201 N1 C114 C113 -4.7(4) . . . . ?
N1 C114 C101 O1 1.2(3) . . . . ?
C113 C114 C101 O1 -175.3(2) . . . . ?
N1 C114 C101 C102 -179.3(2) . . . . ?
C113 C114 C101 C102 4.2(4) . . . . ?
B1 O1 C101 C114 -0.4(3) . . . . ?
B1 O1 C101 C102 -179.9(2) . . . . ?
C114 C101 C102 C103 178.0(3) . . . . ?
O1 C101 C102 C103 -2.6(4) . . . . ?
C114 C101 C102 C107 -2.3(4) . . . . ?
O1 C101 C102 C107 177.2(2) . . . . ?
C103 C102 C107 C106 -0.8(4) . . . . ?
C101 C102 C107 C106 179.4(2) . . . . ?
C103 C102 C107 C108 177.9(2) . . . . ?
C101 C102 C107 C108 -1.9(3) . . . . ?
C102 C107 C106 C105 1.0(4) . . . . ?
C108 C107 C106 C105 -177.7(2) . . . . ?
C107 C106 C105 C104 -0.4(4) . . . . ?
F304 C304 C305 F305 0.1(4) . . . . ?
C303 C304 C305 F305 -179.8(2) . . . . ?
F304 C304 C305 C306 179.9(2) . . . . ?
C303 C304 C305 C306 0.0(4) . . . . ?
F305 C305 C306 F306 0.5(4) . . . . ?
C304 C305 C306 F306 -179.3(2) . . . . ?
F305 C305 C306 C301 179.3(2) . . . . ?
C304 C305 C306 C301 -0.5(4) . . . . ?
F306 C306 C301 C302 179.5(2) . . . . ?
C305 C306 C301 C302 0.7(4) . . . . ?
F306 C306 C301 B1 2.9(4) . . . . ?
C305 C306 C301 B1 -176.0(2) . . . . ?
C306 C301 C302 F302 178.5(2) . . . . ?
B1 C301 C302 F302 -4.9(4) . . . . ?
C306 C301 C302 C303 -0.4(4) . . . . ?
B1 C301 C302 C303 176.2(2) . . . . ?
F304 C304 C303 F303 1.3(4) . . . . ?
C305 C304 C303 F303 -178.8(2) . . . . ?
F304 C304 C303 C302 -179.6(2) . . . . ?
C305 C304 C303 C302 0.3(4) . . . . ?
F302 C302 C303 F303 0.1(4) . . . . ?
C301 C302 C303 F303 179.1(2) . . . . ?
F302 C302 C303 C304 -179.0(2) . . . . ?
C301 C302 C303 C304 -0.1(4) . . . . ?
C203 C204 C205 C206 -1.1(4) . . . . ?
C204 C205 C206 C201 -1.6(4) . . . . ?
C204 C205 C206 C2 178.0(2) . . . . ?
C202 C201 C206 C205 3.8(4) . . . . ?
N1 C201 C206 C205 -174.0(2) . . . . ?
C202 C201 C206 C2 -175.8(2) . . . . ?
N1 C201 C206 C2 6.4(3) . . . . ?
C101 C114 C113 C112 174.5(2) . . . . ?
N1 C114 C113 C112 -0.9(4) . . . . ?
C101 C114 C113 C108 -1.8(3) . . . . ?
N1 C114 C113 C108 -177.3(2) . . . . ?
C112 C113 C108 C109 -1.6(3) . . . . ?
C114 C113 C108 C109 174.9(2) . . . . ?
C112 C113 C108 C107 -178.8(2) . . . . ?
C114 C113 C108 C107 -2.3(3) . . . . ?
C106 C107 C108 C109 5.7(4) . . . . ?
C102 C107 C108 C109 -172.9(2) . . . . ?
C106 C107 C108 C113 -177.3(2) . . . . ?
C102 C107 C108 C113 4.1(4) . . . . ?
C101 C102 C103 C104 179.9(2) . . . . ?
C107 C102 C103 C104 0.2(4) . . . . ?
C102 C103 C104 C105 0.4(4) . . . . ?
C106 C105 C104 C103 -0.3(4) . . . . ?
C113 C108 C109 C110 0.1(4) . . . . ?
C107 C108 C109 C110 177.3(2) . . . . ?
C108 C109 C110 C111 0.8(4) . . . . ?
C109 C110 C111 C112 -0.3(4) . . . . ?
C110 C111 C112 C113 -1.2(4) . . . . ?
C114 C113 C112 C111 -174.0(2) . . . . ?
C108 C113 C112 C111 2.2(4) . . . . ?
C101 O1 B1 N1 -0.6(3) . . . . ?
C101 O1 B1 C301 177.1(2) . . . . ?
C114 N1 B1 O1 1.3(3) . . . . ?
C201 N1 B1 O1 -179.5(2) . . . . ?
C114 N1 B1 C301 -176.3(2) . . . . ?
C201 N1 B1 C301 2.8(4) . . . . ?
C302 C301 B1 O1 127.0(3) . . . . ?
C306 C301 B1 O1 -56.7(4) . . . . ?
C302 C301 B1 N1 -55.7(4) . . . . ?
C306 C301 B1 N1 120.7(3) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_compound_15
_database_code_depnum_ccdc_archive 'CCDC 1535319'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C28 H24 N2'
_chemical_formula_weight         388.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   20.763(4)
_cell_length_b                   5.6764(9)
_cell_length_c                   35.740(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.442(11)
_cell_angle_gamma                90
_cell_volume                     4155.2(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1563
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.07

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5729
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33306
_diffrn_reflns_av_unetI/netI     0.2267
_diffrn_reflns_av_R_equivalents  0.1756
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8109
_reflns_number_gt                3210
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0689P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8109
_refine_ls_number_parameters     561
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2337
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2149
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_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
N01 N 0.2301(2) 0.9999(6) 0.12804(10) 0.0282(10) Uani 1 1 d D . . . .
H1N H 0.209(2) 1.118(7) 0.1385(12) 0.063(18) Uiso 1 1 d D . . . .
N02 N 0.3614(2) 0.9461(7) 0.15968(11) 0.0312(10) Uani 1 1 d D . . . .
H2N H 0.337(2) 1.069(7) 0.1489(13) 0.07(2) Uiso 1 1 d D . . . .
N03 N 0.73142(19) 0.9836(6) 0.13362(10) 0.0255(9) Uani 1 1 d D . . . .
H3N H 0.707(2) 1.090(7) 0.1440(12) 0.051(16) Uiso 1 1 d D . . . .
N04 N 0.8660(2) 0.9419(7) 0.15086(10) 0.0285(10) Uani 1 1 d D . . . .
H4N H 0.841(2) 1.070(6) 0.1417(11) 0.042(15) Uiso 1 1 d D . . . .
C01 C 0.5385(3) 0.6643(10) 0.06071(14) 0.0536(16) Uani 1 1 d . . . . .
H01A H 0.5191 0.7111 0.0349 0.080 Uiso 1 1 calc R U . . .
H01B H 0.5443 0.4929 0.0617 0.080 Uiso 1 1 calc R U . . .
H01C H 0.5810 0.7412 0.0677 0.080 Uiso 1 1 calc R U . . .
C02 C 0.1679(3) 0.8555(9) -0.03229(12) 0.0436(14) Uani 1 1 d . . . . .
H02A H 0.1772 0.6920 -0.0384 0.065 Uiso 1 1 calc R U . . .
H02B H 0.1943 0.9619 -0.0452 0.065 Uiso 1 1 calc R U . . .
H02C H 0.1215 0.8889 -0.0407 0.065 Uiso 1 1 calc R U . . .
C03 C 1.0362(3) 0.7239(9) 0.04401(13) 0.0479(15) Uani 1 1 d . . . . .
H03A H 1.0374 0.5531 0.0402 0.072 Uiso 1 1 calc R U . . .
H03B H 1.0802 0.7812 0.0538 0.072 Uiso 1 1 calc R U . . .
H03C H 1.0199 0.8012 0.0198 0.072 Uiso 1 1 calc R U . . .
C04 C 0.6426(3) 0.8916(9) -0.02612(12) 0.0501(16) Uani 1 1 d . . . . .
H04A H 0.6621 0.7507 -0.0355 0.075 Uiso 1 1 calc R U . . .
H04B H 0.6560 1.0312 -0.0390 0.075 Uiso 1 1 calc R U . . .
H04C H 0.5949 0.8781 -0.0312 0.075 Uiso 1 1 calc R U . . .
C101 C 0.2498(2) 0.8096(7) 0.15376(11) 0.0238(11) Uani 1 1 d . . . . .
C102 C 0.2010(2) 0.6445(8) 0.16250(11) 0.0221(11) Uani 1 1 d . . . . .
C103 C 0.1356(2) 0.6636(8) 0.14591(12) 0.0302(12) Uani 1 1 d . . . . .
H103 H 0.1221 0.7927 0.1296 0.036 Uiso 1 1 calc R U . . .
C104 C 0.0900(2) 0.4984(8) 0.15273(12) 0.0311(12) Uani 1 1 d . . . . .
H104 H 0.0456 0.5135 0.1411 0.037 Uiso 1 1 calc R U . . .
C105 C 0.1099(2) 0.3088(8) 0.17688(12) 0.0273(11) Uani 1 1 d . . . . .
H105 H 0.0790 0.1925 0.1812 0.033 Uiso 1 1 calc R U . . .
C106 C 0.1731(2) 0.2892(8) 0.19433(12) 0.0280(12) Uani 1 1 d . . . . .
H106 H 0.1851 0.1623 0.2114 0.034 Uiso 1 1 calc R U . . .
C107 C 0.2214(2) 0.4538(7) 0.18766(10) 0.0212(11) Uani 1 1 d . . . . .
C108 C 0.2891(2) 0.4366(8) 0.20514(11) 0.0217(10) Uani 1 1 d . . . . .
C109 C 0.3118(2) 0.2603(8) 0.23181(11) 0.0283(11) Uani 1 1 d . . . . .
H109 H 0.2818 0.1473 0.2384 0.034 Uiso 1 1 calc R U . . .
C110 C 0.3760(2) 0.2477(8) 0.24851(12) 0.0333(12) Uani 1 1 d . . . . .
H110 H 0.3902 0.1259 0.2662 0.040 Uiso 1 1 calc R U . . .
C111 C 0.4205(2) 0.4143(8) 0.23950(12) 0.0334(12) Uani 1 1 d . . . . .
H111 H 0.4649 0.4080 0.2514 0.040 Uiso 1 1 calc R U . . .
C112 C 0.4001(2) 0.5858(8) 0.21363(12) 0.0308(12) Uani 1 1 d . . . . .
H112 H 0.4308 0.6970 0.2074 0.037 Uiso 1 1 calc R U . . .
C113 C 0.3350(2) 0.6020(7) 0.19602(11) 0.0235(11) Uani 1 1 d . . . . .
C114 C 0.3137(2) 0.7871(7) 0.16923(11) 0.0227(11) Uani 1 1 d . . . . .
C201 C 0.4060(2) 0.8666(8) 0.13636(11) 0.0256(11) Uani 1 1 d . . . . .
C202 C 0.4570(2) 1.0151(8) 0.13122(13) 0.0361(13) Uani 1 1 d . . . . .
H202 H 0.4624 1.1622 0.1440 0.043 Uiso 1 1 calc R U . . .
C203 C 0.4999(2) 0.9474(9) 0.10724(14) 0.0416(13) Uani 1 1 d . . . . .
H203 H 0.5346 1.0505 0.1040 0.050 Uiso 1 1 calc R U . . .
C204 C 0.4941(2) 0.7376(9) 0.08807(13) 0.0319(12) Uani 1 1 d . . . . .
C205 C 0.4443(2) 0.5890(9) 0.09487(12) 0.0364(13) Uani 1 1 d . . . . .
H205 H 0.4403 0.4389 0.0829 0.044 Uiso 1 1 calc R U . . .
C206 C 0.4005(2) 0.6510(8) 0.11835(12) 0.0324(12) Uani 1 1 d . . . . .
H206 H 0.3666 0.5454 0.1221 0.039 Uiso 1 1 calc R U . . .
C301 C 0.2138(2) 0.9605(8) 0.08900(11) 0.0235(11) Uani 1 1 d . . . . .
C302 C 0.2307(2) 0.7527(8) 0.07238(12) 0.0292(12) Uani 1 1 d . . . . .
H302 H 0.2527 0.6316 0.0878 0.035 Uiso 1 1 calc R U . . .
C303 C 0.2156(2) 0.7214(8) 0.03353(12) 0.0321(12) Uani 1 1 d . . . . .
H303 H 0.2272 0.5773 0.0229 0.038 Uiso 1 1 calc R U . . .
C304 C 0.1844(2) 0.8919(8) 0.00976(12) 0.0293(12) Uani 1 1 d . . . . .
C305 C 0.1679(2) 1.0983(9) 0.02639(12) 0.0346(13) Uani 1 1 d . . . . .
H305 H 0.1464 1.2196 0.0108 0.042 Uiso 1 1 calc R U . . .
C306 C 0.1820(2) 1.1324(8) 0.06538(12) 0.0323(12) Uani 1 1 d . . . . .
H306 H 0.1698 1.2758 0.0760 0.039 Uiso 1 1 calc R U . . .
C401 C 0.7592(2) 0.7946(7) 0.15687(11) 0.0212(11) Uani 1 1 d . . . . .
C402 C 0.7174(2) 0.6248(8) 0.17142(11) 0.0233(11) Uani 1 1 d . . . . .
C403 C 0.6495(2) 0.6350(8) 0.16088(12) 0.0302(12) Uani 1 1 d . . . . .
H403 H 0.6304 0.7586 0.1449 0.036 Uiso 1 1 calc R U . . .
C404 C 0.6099(3) 0.4676(9) 0.17348(12) 0.0362(13) Uani 1 1 d . . . . .
H404 H 0.5639 0.4755 0.1659 0.043 Uiso 1 1 calc R U . . .
C405 C 0.6372(3) 0.2874(8) 0.19725(13) 0.0316(12) Uani 1 1 d . . . . .
H405 H 0.6100 0.1716 0.2058 0.038 Uiso 1 1 calc R U . . .
C406 C 0.7037(2) 0.2772(8) 0.20836(12) 0.0299(12) Uani 1 1 d . . . . .
H406 H 0.7215 0.1559 0.2253 0.036 Uiso 1 1 calc R U . . .
C407 C 0.7462(2) 0.4401(8) 0.19558(11) 0.0239(11) Uani 1 1 d . . . . .
C408 C 0.8166(2) 0.4264(7) 0.20537(11) 0.0231(11) Uani 1 1 d . . . . .
C409 C 0.8484(2) 0.2581(8) 0.23084(11) 0.0309(12) Uani 1 1 d . . . . .
H409 H 0.8231 0.1459 0.2418 0.037 Uiso 1 1 calc R U . . .
C410 C 0.9145(3) 0.2522(9) 0.24014(13) 0.0390(13) Uani 1 1 d . . . . .
H410 H 0.9346 0.1358 0.2573 0.047 Uiso 1 1 calc R U . . .
C411 C 0.9527(2) 0.4138(8) 0.22494(12) 0.0353(13) Uani 1 1 d . . . . .
H411 H 0.9989 0.4082 0.2317 0.042 Uiso 1 1 calc R U . . .
C412 C 0.9244(2) 0.5813(8) 0.20023(11) 0.0307(12) Uani 1 1 d . . . . .
H412 H 0.9510 0.6914 0.1898 0.037 Uiso 1 1 calc R U . . .
C413 C 0.8558(2) 0.5923(8) 0.18998(11) 0.0243(11) Uani 1 1 d . . . . .
C414 C 0.8253(2) 0.7744(7) 0.16462(11) 0.0252(11) Uani 1 1 d . . . . .
C501 C 0.9082(2) 0.8795(8) 0.12490(11) 0.0249(11) Uani 1 1 d . . . . .
C502 C 0.9561(2) 1.0372(8) 0.11863(11) 0.0279(12) Uani 1 1 d . . . . .
H502 H 0.9612 1.1810 0.1324 0.033 Uiso 1 1 calc R U . . .
C503 C 0.9968(2) 0.9884(8) 0.09260(12) 0.0325(12) Uani 1 1 d . . . . .
H503 H 1.0291 1.0998 0.0886 0.039 Uiso 1 1 calc R U . . .
C504 C 0.9912(2) 0.7798(8) 0.07226(12) 0.0306(12) Uani 1 1 d . . . . .
C505 C 0.9444(2) 0.6215(8) 0.07933(12) 0.0315(12) Uani 1 1 d . . . . .
H505 H 0.9406 0.4754 0.0662 0.038 Uiso 1 1 calc R U . . .
C506 C 0.9028(2) 0.6682(8) 0.10496(11) 0.0266(11) Uani 1 1 d . . . . .
H506 H 0.8706 0.5561 0.1089 0.032 Uiso 1 1 calc R U . . .
C601 C 0.7086(2) 0.9537(8) 0.09479(11) 0.0232(11) Uani 1 1 d . . . . .
C602 C 0.7221(2) 0.7544(7) 0.07512(12) 0.0258(11) Uani 1 1 d . . . . .
H602 H 0.7461 0.6284 0.0882 0.031 Uiso 1 1 calc R U . . .
C603 C 0.7008(2) 0.7382(8) 0.03644(12) 0.0283(12) Uani 1 1 d . . . . .
H603 H 0.7108 0.6003 0.0235 0.034 Uiso 1 1 calc R U . . .
C604 C 0.6655(2) 0.9143(9) 0.01603(12) 0.0315(12) Uani 1 1 d . . . . .
C605 C 0.6515(2) 1.1133(8) 0.03606(13) 0.0348(13) Uani 1 1 d . . . . .
H605 H 0.6271 1.2384 0.0229 0.042 Uiso 1 1 calc R U . . .
C606 C 0.6722(2) 1.1322(8) 0.07457(12) 0.0294(12) Uani 1 1 d . . . . .
H606 H 0.6616 1.2691 0.0876 0.035 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
N01 C301 1.399(5) . ?
N01 C101 1.434(5) . ?
N02 C201 1.418(6) . ?
N02 C114 1.422(6) . ?
N03 C601 1.401(5) . ?
N03 C401 1.420(5) . ?
N04 C414 1.413(5) . ?
N04 C501 1.421(6) . ?
C01 C204 1.508(6) . ?
C02 C304 1.500(6) . ?
C03 C504 1.516(6) . ?
C04 C604 1.509(6) . ?
C101 C114 1.356(6) . ?
C101 C102 1.452(6) . ?
C102 C103 1.394(6) . ?
C102 C107 1.426(6) . ?
C103 C104 1.383(6) . ?
C104 C105 1.399(6) . ?
C105 C106 1.362(6) . ?
C106 C107 1.419(6) . ?
C107 C108 1.446(6) . ?
C108 C109 1.408(6) . ?
C108 C113 1.414(6) . ?
C109 C110 1.371(6) . ?
C110 C111 1.396(6) . ?
C111 C112 1.361(6) . ?
C112 C113 1.396(6) . ?
C113 C114 1.442(6) . ?
C201 C206 1.379(6) . ?
C201 C202 1.388(6) . ?
C202 C203 1.389(6) . ?
C203 C204 1.369(6) . ?
C204 C205 1.386(6) . ?
C205 C206 1.382(6) . ?
C301 C306 1.384(6) . ?
C301 C302 1.391(6) . ?
C302 C303 1.384(6) . ?
C303 C304 1.377(6) . ?
C304 C305 1.382(6) . ?
C305 C306 1.390(6) . ?
C401 C414 1.360(6) . ?
C401 C402 1.450(6) . ?
C402 C403 1.399(6) . ?
C402 C407 1.426(6) . ?
C403 C404 1.379(6) . ?
C404 C405 1.390(6) . ?
C405 C406 1.373(7) . ?
C406 C407 1.406(6) . ?
C407 C408 1.448(6) . ?
C408 C409 1.407(6) . ?
C408 C413 1.414(6) . ?
C409 C410 1.357(7) . ?
C410 C411 1.381(6) . ?
C411 C412 1.364(6) . ?
C412 C413 1.412(6) . ?
C413 C414 1.450(6) . ?
C501 C502 1.384(6) . ?
C501 C506 1.391(6) . ?
C502 C503 1.383(6) . ?
C503 C504 1.384(6) . ?
C504 C505 1.377(6) . ?
C505 C506 1.385(6) . ?
C601 C602 1.385(6) . ?
C601 C606 1.393(6) . ?
C602 C603 1.384(6) . ?
C603 C604 1.376(6) . ?
C604 C605 1.394(6) . ?
C605 C606 1.377(6) . ?

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
C301 N01 C101 121.1(4) . . ?
C201 N02 C114 119.2(4) . . ?
C601 N03 C401 121.8(4) . . ?
C414 N04 C501 121.8(4) . . ?
C114 C101 N01 119.3(4) . . ?
C114 C101 C102 121.5(4) . . ?
N01 C101 C102 119.2(4) . . ?
C103 C102 C107 119.6(4) . . ?
C103 C102 C101 121.6(4) . . ?
C107 C102 C101 118.7(4) . . ?
C104 C103 C102 121.3(4) . . ?
C103 C104 C105 119.2(5) . . ?
C106 C105 C104 120.7(4) . . ?
C105 C106 C107 121.6(4) . . ?
C106 C107 C102 117.5(4) . . ?
C106 C107 C108 123.1(4) . . ?
C102 C107 C108 119.4(4) . . ?
C109 C108 C113 117.7(4) . . ?
C109 C108 C107 122.3(4) . . ?
C113 C108 C107 120.0(4) . . ?
C110 C109 C108 121.7(5) . . ?
C109 C110 C111 119.8(4) . . ?
C112 C111 C110 119.8(5) . . ?
C111 C112 C113 121.6(4) . . ?
C112 C113 C108 119.4(4) . . ?
C112 C113 C114 121.1(4) . . ?
C108 C113 C114 119.4(4) . . ?
C101 C114 N02 121.0(4) . . ?
C101 C114 C113 120.9(4) . . ?
N02 C114 C113 118.1(4) . . ?
C206 C201 C202 119.0(4) . . ?
C206 C201 N02 123.0(4) . . ?
C202 C201 N02 118.0(4) . . ?
C201 C202 C203 119.6(5) . . ?
C204 C203 C202 122.5(5) . . ?
C203 C204 C205 116.7(5) . . ?
C203 C204 C01 123.5(5) . . ?
C205 C204 C01 119.9(5) . . ?
C206 C205 C204 122.4(5) . . ?
C201 C206 C205 119.8(4) . . ?
C306 C301 C302 117.7(4) . . ?
C306 C301 N01 120.6(4) . . ?
C302 C301 N01 121.6(4) . . ?
C303 C302 C301 120.4(4) . . ?
C304 C303 C302 122.3(4) . . ?
C303 C304 C305 117.1(4) . . ?
C303 C304 C02 121.9(4) . . ?
C305 C304 C02 121.0(4) . . ?
C304 C305 C306 121.5(4) . . ?
C301 C306 C305 121.0(4) . . ?
C414 C401 N03 118.8(4) . . ?
C414 C401 C402 121.0(4) . . ?
N03 C401 C402 120.2(4) . . ?
C403 C402 C407 119.9(4) . . ?
C403 C402 C401 120.8(4) . . ?
C407 C402 C401 119.3(4) . . ?
C404 C403 C402 120.7(5) . . ?
C403 C404 C405 120.1(5) . . ?
C406 C405 C404 119.8(5) . . ?
C405 C406 C407 122.2(5) . . ?
C406 C407 C402 117.1(4) . . ?
C406 C407 C408 123.3(4) . . ?
C402 C407 C408 119.5(4) . . ?
C409 C408 C413 117.7(4) . . ?
C409 C408 C407 122.7(4) . . ?
C413 C408 C407 119.5(4) . . ?
C410 C409 C408 121.5(4) . . ?
C409 C410 C411 120.7(5) . . ?
C412 C411 C410 120.2(5) . . ?
C411 C412 C413 120.6(4) . . ?
C412 C413 C408 119.3(4) . . ?
C412 C413 C414 120.8(4) . . ?
C408 C413 C414 119.8(4) . . ?
C401 C414 N04 120.9(4) . . ?
C401 C414 C413 120.7(4) . . ?
N04 C414 C413 118.2(4) . . ?
C502 C501 C506 118.3(4) . . ?
C502 C501 N04 118.8(4) . . ?
C506 C501 N04 122.9(4) . . ?
C503 C502 C501 120.9(4) . . ?
C502 C503 C504 121.1(4) . . ?
C505 C504 C503 117.5(4) . . ?
C505 C504 C03 121.0(4) . . ?
C503 C504 C03 121.4(4) . . ?
C504 C505 C506 122.2(5) . . ?
C505 C506 C501 119.8(4) . . ?
C602 C601 C606 117.9(4) . . ?
C602 C601 N03 122.6(4) . . ?
C606 C601 N03 119.5(4) . . ?
C603 C602 C601 120.2(4) . . ?
C604 C603 C602 122.5(4) . . ?
C603 C604 C605 117.0(4) . . ?
C603 C604 C04 121.4(4) . . ?
C605 C604 C04 121.6(5) . . ?
C606 C605 C604 121.3(4) . . ?
C605 C606 C601 121.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C301 N01 C101 C114 105.6(5) . . . . ?
C301 N01 C101 C102 -74.1(5) . . . . ?
C114 C101 C102 C103 -178.4(4) . . . . ?
N01 C101 C102 C103 1.3(6) . . . . ?
C114 C101 C102 C107 -0.6(6) . . . . ?
N01 C101 C102 C107 179.0(4) . . . . ?
C107 C102 C103 C104 -1.3(6) . . . . ?
C101 C102 C103 C104 176.4(4) . . . . ?
C102 C103 C104 C105 0.2(7) . . . . ?
C103 C104 C105 C106 1.7(7) . . . . ?
C104 C105 C106 C107 -2.4(7) . . . . ?
C105 C106 C107 C102 1.3(6) . . . . ?
C105 C106 C107 C108 -178.9(4) . . . . ?
C103 C102 C107 C106 0.6(6) . . . . ?
C101 C102 C107 C106 -177.2(4) . . . . ?
C103 C102 C107 C108 -179.3(4) . . . . ?
C101 C102 C107 C108 3.0(5) . . . . ?
C106 C107 C108 C109 -3.4(6) . . . . ?
C102 C107 C108 C109 176.5(4) . . . . ?
C106 C107 C108 C113 177.5(4) . . . . ?
C102 C107 C108 C113 -2.7(6) . . . . ?
C113 C108 C109 C110 -0.1(6) . . . . ?
C107 C108 C109 C110 -179.2(4) . . . . ?
C108 C109 C110 C111 0.8(7) . . . . ?
C109 C110 C111 C112 -1.2(7) . . . . ?
C110 C111 C112 C113 0.9(7) . . . . ?
C111 C112 C113 C108 -0.1(7) . . . . ?
C111 C112 C113 C114 178.7(4) . . . . ?
C109 C108 C113 C112 -0.3(6) . . . . ?
C107 C108 C113 C112 178.8(4) . . . . ?
C109 C108 C113 C114 -179.2(4) . . . . ?
C107 C108 C113 C114 0.0(6) . . . . ?
N01 C101 C114 N02 -1.4(6) . . . . ?
C102 C101 C114 N02 178.3(4) . . . . ?
N01 C101 C114 C113 178.2(4) . . . . ?
C102 C101 C114 C113 -2.1(6) . . . . ?
C201 N02 C114 C101 -107.8(5) . . . . ?
C201 N02 C114 C113 72.5(5) . . . . ?
C112 C113 C114 C101 -176.4(4) . . . . ?
C108 C113 C114 C101 2.4(6) . . . . ?
C112 C113 C114 N02 3.2(6) . . . . ?
C108 C113 C114 N02 -177.9(4) . . . . ?
C114 N02 C201 C206 8.6(7) . . . . ?
C114 N02 C201 C202 -172.3(4) . . . . ?
C206 C201 C202 C203 2.0(7) . . . . ?
N02 C201 C202 C203 -177.2(4) . . . . ?
C201 C202 C203 C204 0.2(7) . . . . ?
C202 C203 C204 C205 -2.6(7) . . . . ?
C202 C203 C204 C01 177.5(5) . . . . ?
C203 C204 C205 C206 2.9(7) . . . . ?
C01 C204 C205 C206 -177.1(4) . . . . ?
C202 C201 C206 C205 -1.6(7) . . . . ?
N02 C201 C206 C205 177.5(4) . . . . ?
C204 C205 C206 C201 -0.9(7) . . . . ?
C101 N01 C301 C306 166.4(4) . . . . ?
C101 N01 C301 C302 -16.0(7) . . . . ?
C306 C301 C302 C303 -0.3(7) . . . . ?
N01 C301 C302 C303 -178.0(4) . . . . ?
C301 C302 C303 C304 0.7(7) . . . . ?
C302 C303 C304 C305 -0.5(7) . . . . ?
C302 C303 C304 C02 -179.6(4) . . . . ?
C303 C304 C305 C306 -0.1(7) . . . . ?
C02 C304 C305 C306 179.0(4) . . . . ?
C302 C301 C306 C305 -0.2(7) . . . . ?
N01 C301 C306 C305 177.5(4) . . . . ?
C304 C305 C306 C301 0.5(7) . . . . ?
C601 N03 C401 C414 98.0(5) . . . . ?
C601 N03 C401 C402 -81.0(5) . . . . ?
C414 C401 C402 C403 -174.8(4) . . . . ?
N03 C401 C402 C403 4.2(6) . . . . ?
C414 C401 C402 C407 2.8(6) . . . . ?
N03 C401 C402 C407 -178.3(3) . . . . ?
C407 C402 C403 C404 -0.2(6) . . . . ?
C401 C402 C403 C404 177.3(4) . . . . ?
C402 C403 C404 C405 0.7(7) . . . . ?
C403 C404 C405 C406 0.4(7) . . . . ?
C404 C405 C406 C407 -2.0(7) . . . . ?
C405 C406 C407 C402 2.3(6) . . . . ?
C405 C406 C407 C408 -176.9(4) . . . . ?
C403 C402 C407 C406 -1.2(6) . . . . ?
C401 C402 C407 C406 -178.8(4) . . . . ?
C403 C402 C407 C408 178.0(4) . . . . ?
C401 C402 C407 C408 0.5(6) . . . . ?
C406 C407 C408 C409 -4.8(6) . . . . ?
C402 C407 C408 C409 176.0(4) . . . . ?
C406 C407 C408 C413 177.4(4) . . . . ?
C402 C407 C408 C413 -1.8(6) . . . . ?
C413 C408 C409 C410 -0.7(6) . . . . ?
C407 C408 C409 C410 -178.6(4) . . . . ?
C408 C409 C410 C411 0.5(7) . . . . ?
C409 C410 C411 C412 -0.2(7) . . . . ?
C410 C411 C412 C413 0.2(7) . . . . ?
C411 C412 C413 C408 -0.5(6) . . . . ?
C411 C412 C413 C414 178.1(4) . . . . ?
C409 C408 C413 C412 0.8(6) . . . . ?
C407 C408 C413 C412 178.7(4) . . . . ?
C409 C408 C413 C414 -177.9(4) . . . . ?
C407 C408 C413 C414 0.1(6) . . . . ?
N03 C401 C414 N04 1.9(6) . . . . ?
C402 C401 C414 N04 -179.1(4) . . . . ?
N03 C401 C414 C413 176.4(4) . . . . ?
C402 C401 C414 C413 -4.6(6) . . . . ?
C501 N04 C414 C401 -116.6(5) . . . . ?
C501 N04 C414 C413 68.7(5) . . . . ?
C412 C413 C414 C401 -175.4(4) . . . . ?
C408 C413 C414 C401 3.2(6) . . . . ?
C412 C413 C414 N04 -0.8(6) . . . . ?
C408 C413 C414 N04 177.8(4) . . . . ?
C414 N04 C501 C502 -166.7(4) . . . . ?
C414 N04 C501 C506 14.4(7) . . . . ?
C506 C501 C502 C503 1.3(7) . . . . ?
N04 C501 C502 C503 -177.6(4) . . . . ?
C501 C502 C503 C504 -0.5(7) . . . . ?
C502 C503 C504 C505 -1.0(7) . . . . ?
C502 C503 C504 C03 -179.3(4) . . . . ?
C503 C504 C505 C506 1.7(7) . . . . ?
C03 C504 C505 C506 -180.0(4) . . . . ?
C504 C505 C506 C501 -0.9(7) . . . . ?
C502 C501 C506 C505 -0.6(6) . . . . ?
N04 C501 C506 C505 178.3(4) . . . . ?
C401 N03 C601 C602 -12.2(6) . . . . ?
C401 N03 C601 C606 169.4(4) . . . . ?
C606 C601 C602 C603 1.2(6) . . . . ?
N03 C601 C602 C603 -177.2(4) . . . . ?
C601 C602 C603 C604 -0.4(7) . . . . ?
C602 C603 C604 C605 -0.3(7) . . . . ?
C602 C603 C604 C04 -179.8(4) . . . . ?
C603 C604 C605 C606 0.2(7) . . . . ?
C04 C604 C605 C606 179.6(4) . . . . ?
C604 C605 C606 C601 0.7(7) . . . . ?
C602 C601 C606 C605 -1.3(6) . . . . ?
N03 C601 C606 C605 177.1(4) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_compound_04
_database_code_depnum_ccdc_archive 'CCDC 1535314'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C34 H17 B F10 N O'
_chemical_formula_weight         656.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   17.968(3)
_cell_length_b                   22.919(4)
_cell_length_c                   16.083(3)
_cell_angle_alpha                90
_cell_angle_beta                 122.027(7)
_cell_angle_gamma                90
_cell_volume                     5615.2(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3699
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      21.07

_exptl_crystal_description       shard
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             2648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22087
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.605
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4951
_reflns_number_gt                3027
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0800P)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         4951
_refine_ls_number_parameters     426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.75852(14) 0.06691(9) 0.27162(15) 0.0248(5) Uani 1 1 d . . . . .
B1 B 0.6699(2) 0.08621(14) 0.2651(2) 0.0276(8) Uani 1 1 d . . . . .
O1 O 0.64244(12) 0.02748(8) 0.28311(14) 0.0312(5) Uani 1 1 d . . . . .
F302 F 0.79346(11) 0.06162(7) 0.47033(11) 0.0384(4) Uani 1 1 d . . . . .
F303 F 0.81388(13) 0.11829(8) 0.62513(13) 0.0543(5) Uani 1 1 d . . . . .
F304 F 0.71717(15) 0.21498(9) 0.60230(15) 0.0646(6) Uani 1 1 d . . . . .
F305 F 0.59955(13) 0.25469(8) 0.41811(16) 0.0614(6) Uani 1 1 d . . . . .
F306 F 0.57947(12) 0.20088(8) 0.26199(14) 0.0508(5) Uani 1 1 d . . . . .
F402 F 0.68432(10) 0.19655(7) 0.18701(11) 0.0362(4) Uani 1 1 d . . . . .
F403 F 0.57786(12) 0.23846(7) 0.00599(13) 0.0457(5) Uani 1 1 d . . . . .
F404 F 0.43168(12) 0.17871(8) -0.12523(12) 0.0513(5) Uani 1 1 d . . . . .
F405 F 0.39447(12) 0.07510(8) -0.07310(13) 0.0544(5) Uani 1 1 d . . . . .
F406 F 0.50073(11) 0.03037(8) 0.10405(13) 0.0492(5) Uani 1 1 d . . . . .
C1 C 0.8830(2) 0.16028(14) 0.3805(2) 0.0396(8) Uani 1 1 d . . . . .
H1A H 0.9348 0.1857 0.4098 0.059 Uiso 1 1 calc R U . . .
H1B H 0.8962 0.1253 0.4211 0.059 Uiso 1 1 calc R U . . .
H1C H 0.8338 0.1812 0.3768 0.059 Uiso 1 1 calc R U . . .
C2 C 0.7206(2) 0.02851(13) 0.0816(2) 0.0376(8) Uani 1 1 d . . . . .
H2A H 0.7069 0.0279 0.0139 0.056 Uiso 1 1 calc R U . . .
H2B H 0.6663 0.0332 0.0813 0.056 Uiso 1 1 calc R U . . .
H2C H 0.7491 -0.0083 0.1141 0.056 Uiso 1 1 calc R U . . .
C101 C 0.70263(19) -0.01212(12) 0.30171(19) 0.0275(7) Uani 1 1 d . . . . .
C102 C 0.6957(2) -0.07118(13) 0.32256(19) 0.0320(7) Uani 1 1 d . . . . .
C103 C 0.6245(2) -0.09107(14) 0.3275(2) 0.0406(8) Uani 1 1 d . . . . .
H103 H 0.5793 -0.0647 0.3166 0.049 Uiso 1 1 calc R U . . .
C104 C 0.6198(3) -0.14927(15) 0.3482(2) 0.0548(10) Uani 1 1 d . . . . .
H104 H 0.5721 -0.1631 0.3525 0.066 Uiso 1 1 calc R U . . .
C105 C 0.6859(3) -0.18686(16) 0.3624(2) 0.0585(11) Uani 1 1 d . . . . .
H105 H 0.6832 -0.2266 0.3773 0.070 Uiso 1 1 calc R U . . .
C106 C 0.7548(3) -0.16859(14) 0.3556(2) 0.0503(10) Uani 1 1 d . . . . .
H106 H 0.7977 -0.1961 0.3637 0.060 Uiso 1 1 calc R U . . .
C107 C 0.7635(2) -0.10975(13) 0.33684(19) 0.0351(8) Uani 1 1 d . . . . .
C108 C 0.8398(2) -0.08755(13) 0.3372(2) 0.0369(8) Uani 1 1 d . . . . .
C109 C 0.9100(2) -0.12401(16) 0.3572(2) 0.0502(10) Uani 1 1 d . . . . .
H109 H 0.9061 -0.1645 0.3668 0.060 Uiso 1 1 calc R U . . .
C110 C 0.9842(3) -0.10315(18) 0.3634(3) 0.0601(11) Uani 1 1 d . . . . .
H110 H 1.0302 -0.1292 0.3758 0.072 Uiso 1 1 calc R U . . .
C111 C 0.9925(2) -0.04395(18) 0.3515(2) 0.0540(10) Uani 1 1 d . . . . .
H111 H 1.0451 -0.0293 0.3589 0.065 Uiso 1 1 calc R U . . .
C112 C 0.9243(2) -0.00638(15) 0.3290(2) 0.0414(8) Uani 1 1 d . . . . .
H112 H 0.9297 0.0340 0.3198 0.050 Uiso 1 1 calc R U . . .
C113 C 0.84662(19) -0.02760(13) 0.31967(19) 0.0320(7) Uani 1 1 d . . . . .
C114 C 0.77336(18) 0.00997(12) 0.29726(18) 0.0262(7) Uani 1 1 d . . . . .
C201 C 0.80093(17) 0.09684(12) 0.22869(19) 0.0246(6) Uani 1 1 d . . . . .
C202 C 0.85904(17) 0.14282(13) 0.2792(2) 0.0286(7) Uani 1 1 d . . . . .
C203 C 0.89616(19) 0.17092(14) 0.2334(2) 0.0371(8) Uani 1 1 d . . . . .
H203 H 0.9350 0.2027 0.2655 0.045 Uiso 1 1 calc R U . . .
C204 C 0.8779(2) 0.15376(15) 0.1420(2) 0.0427(8) Uani 1 1 d . . . . .
H204 H 0.9044 0.1735 0.1122 0.051 Uiso 1 1 calc R U . . .
C205 C 0.8215(2) 0.10818(14) 0.0944(2) 0.0387(8) Uani 1 1 d . . . . .
H205 H 0.8095 0.0966 0.0317 0.046 Uiso 1 1 calc R U . . .
C206 C 0.78142(18) 0.07851(13) 0.1359(2) 0.0292(7) Uani 1 1 d . . . . .
C301 C 0.68488(18) 0.12766(13) 0.3563(2) 0.0299(7) Uani 1 1 d . . . . .
C302 C 0.74324(19) 0.11000(13) 0.4529(2) 0.0316(7) Uani 1 1 d . . . . .
C303 C 0.7551(2) 0.13824(14) 0.5343(2) 0.0389(8) Uani 1 1 d . . . . .
C304 C 0.7059(2) 0.18701(14) 0.5228(3) 0.0428(9) Uani 1 1 d . . . . .
C305 C 0.6478(2) 0.20648(13) 0.4304(3) 0.0422(8) Uani 1 1 d . . . . .
C306 C 0.6382(2) 0.17769(13) 0.3499(2) 0.0364(8) Uani 1 1 d . . . . .
C401 C 0.59994(17) 0.11072(12) 0.1555(2) 0.0265(7) Uani 1 1 d . . . . .
C402 C 0.61402(18) 0.16377(12) 0.1235(2) 0.0283(7) Uani 1 1 d . . . . .
C403 C 0.55972(19) 0.18675(12) 0.0320(2) 0.0332(7) Uani 1 1 d . . . . .
C404 C 0.48547(19) 0.15699(13) -0.0349(2) 0.0354(8) Uani 1 1 d . . . . .
C405 C 0.46704(19) 0.10461(14) -0.0084(2) 0.0369(8) Uani 1 1 d . . . . .
C406 C 0.52366(19) 0.08273(13) 0.0847(2) 0.0332(7) 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
N1 C114 1.352(3) . ?
N1 C201 1.444(3) . ?
N1 B1 1.600(4) . ?
B1 O1 1.514(4) . ?
B1 C401 1.628(4) . ?
B1 C301 1.647(4) . ?
O1 C101 1.319(3) . ?
F302 C302 1.362(3) . ?
F303 C303 1.350(4) . ?
F304 C304 1.346(3) . ?
F305 C305 1.353(3) . ?
F306 C306 1.346(4) . ?
F402 C402 1.355(3) . ?
F403 C403 1.353(3) . ?
F404 C404 1.343(3) . ?
F405 C405 1.342(3) . ?
F406 C406 1.357(3) . ?
C1 C202 1.502(4) . ?
C2 C206 1.502(4) . ?
C101 C114 1.405(4) . ?
C101 C102 1.416(4) . ?
C102 C103 1.400(4) . ?
C102 C107 1.421(4) . ?
C103 C104 1.388(4) . ?
C104 C105 1.385(5) . ?
C105 C106 1.366(5) . ?
C106 C107 1.409(4) . ?
C107 C108 1.459(4) . ?
C108 C109 1.402(4) . ?
C108 C113 1.421(4) . ?
C109 C110 1.370(5) . ?
C110 C111 1.389(5) . ?
C111 C112 1.380(4) . ?
C112 C113 1.408(4) . ?
C113 C114 1.449(4) . ?
C201 C202 1.400(4) . ?
C201 C206 1.404(4) . ?
C202 C203 1.388(4) . ?
C203 C204 1.383(4) . ?
C204 C205 1.372(4) . ?
C205 C206 1.391(4) . ?
C301 C306 1.392(4) . ?
C301 C302 1.396(4) . ?
C302 C303 1.372(4) . ?
C303 C304 1.375(5) . ?
C304 C305 1.361(5) . ?
C305 C306 1.381(4) . ?
C401 C406 1.390(4) . ?
C401 C402 1.395(4) . ?
C402 C403 1.368(4) . ?
C403 C404 1.371(4) . ?
C404 C405 1.372(4) . ?
C405 C406 1.383(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
C114 N1 C201 122.4(2) . . ?
C114 N1 B1 108.4(2) . . ?
C201 N1 B1 126.6(2) . . ?
O1 B1 N1 99.0(2) . . ?
O1 B1 C401 111.8(2) . . ?
N1 B1 C401 109.7(2) . . ?
O1 B1 C301 104.9(2) . . ?
N1 B1 C301 114.5(2) . . ?
C401 B1 C301 115.6(2) . . ?
C101 O1 B1 110.1(2) . . ?
O1 C101 C114 113.3(2) . . ?
O1 C101 C102 123.2(3) . . ?
C114 C101 C102 123.5(3) . . ?
C103 C102 C101 121.5(3) . . ?
C103 C102 C107 121.3(3) . . ?
C101 C102 C107 117.2(3) . . ?
C104 C103 C102 120.0(3) . . ?
C105 C104 C103 118.8(4) . . ?
C106 C105 C104 122.1(3) . . ?
C105 C106 C107 121.2(3) . . ?
C106 C107 C102 116.6(3) . . ?
C106 C107 C108 122.9(3) . . ?
C102 C107 C108 120.4(3) . . ?
C109 C108 C113 117.4(3) . . ?
C109 C108 C107 121.5(3) . . ?
C113 C108 C107 121.1(3) . . ?
C110 C109 C108 122.1(3) . . ?
C109 C110 C111 120.1(3) . . ?
C112 C111 C110 120.0(4) . . ?
C111 C112 C113 120.3(3) . . ?
C112 C113 C108 119.8(3) . . ?
C112 C113 C114 122.6(3) . . ?
C108 C113 C114 117.5(3) . . ?
N1 C114 C101 109.0(2) . . ?
N1 C114 C113 131.0(3) . . ?
C101 C114 C113 120.0(3) . . ?
C202 C201 C206 122.1(2) . . ?
C202 C201 N1 120.0(2) . . ?
C206 C201 N1 117.9(2) . . ?
C203 C202 C201 117.5(3) . . ?
C203 C202 C1 120.7(3) . . ?
C201 C202 C1 121.8(3) . . ?
C204 C203 C202 121.6(3) . . ?
C205 C204 C203 119.9(3) . . ?
C204 C205 C206 121.5(3) . . ?
C205 C206 C201 117.6(3) . . ?
C205 C206 C2 119.7(3) . . ?
C201 C206 C2 122.8(2) . . ?
C306 C301 C302 112.9(3) . . ?
C306 C301 B1 127.0(3) . . ?
C302 C301 B1 119.7(3) . . ?
F302 C302 C303 115.9(3) . . ?
F302 C302 C301 119.4(2) . . ?
C303 C302 C301 124.7(3) . . ?
F303 C303 C302 120.6(3) . . ?
F303 C303 C304 120.0(3) . . ?
C302 C303 C304 119.4(3) . . ?
F304 C304 C305 121.5(3) . . ?
F304 C304 C303 119.8(3) . . ?
C305 C304 C303 118.7(3) . . ?
F305 C305 C304 119.3(3) . . ?
F305 C305 C306 120.1(3) . . ?
C304 C305 C306 120.6(3) . . ?
F306 C306 C305 115.8(3) . . ?
F306 C306 C301 120.6(3) . . ?
C305 C306 C301 123.6(3) . . ?
C406 C401 C402 113.2(3) . . ?
C406 C401 B1 126.0(3) . . ?
C402 C401 B1 120.8(2) . . ?
F402 C402 C403 116.4(2) . . ?
F402 C402 C401 119.0(2) . . ?
C403 C402 C401 124.5(3) . . ?
F403 C403 C402 121.2(3) . . ?
F403 C403 C404 119.1(3) . . ?
C402 C403 C404 119.7(3) . . ?
F404 C404 C403 120.5(3) . . ?
F404 C404 C405 120.4(3) . . ?
C403 C404 C405 119.1(3) . . ?
F405 C405 C404 119.7(3) . . ?
F405 C405 C406 120.7(3) . . ?
C404 C405 C406 119.6(3) . . ?
F406 C406 C405 115.5(3) . . ?
F406 C406 C401 120.5(3) . . ?
C405 C406 C401 124.0(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
C114 N1 B1 O1 -4.7(3) . . . . ?
C201 N1 B1 O1 156.9(2) . . . . ?
C114 N1 B1 C401 -121.8(2) . . . . ?
C201 N1 B1 C401 39.8(3) . . . . ?
C114 N1 B1 C301 106.3(3) . . . . ?
C201 N1 B1 C301 -92.1(3) . . . . ?
N1 B1 O1 C101 3.7(3) . . . . ?
C401 B1 O1 C101 119.2(2) . . . . ?
C301 B1 O1 C101 -114.8(2) . . . . ?
B1 O1 C101 C114 -1.6(3) . . . . ?
B1 O1 C101 C102 179.3(3) . . . . ?
O1 C101 C102 C103 -1.8(4) . . . . ?
C114 C101 C102 C103 179.2(3) . . . . ?
O1 C101 C102 C107 177.2(2) . . . . ?
C114 C101 C102 C107 -1.8(4) . . . . ?
C101 C102 C103 C104 -179.9(3) . . . . ?
C107 C102 C103 C104 1.0(4) . . . . ?
C102 C103 C104 C105 -0.8(5) . . . . ?
C103 C104 C105 C106 -0.7(5) . . . . ?
C104 C105 C106 C107 2.1(5) . . . . ?
C105 C106 C107 C102 -1.8(4) . . . . ?
C105 C106 C107 C108 174.7(3) . . . . ?
C103 C102 C107 C106 0.3(4) . . . . ?
C101 C102 C107 C106 -178.8(2) . . . . ?
C103 C102 C107 C108 -176.4(3) . . . . ?
C101 C102 C107 C108 4.6(4) . . . . ?
C106 C107 C108 C109 -0.5(4) . . . . ?
C102 C107 C108 C109 175.9(3) . . . . ?
C106 C107 C108 C113 -178.8(3) . . . . ?
C102 C107 C108 C113 -2.4(4) . . . . ?
C113 C108 C109 C110 2.3(5) . . . . ?
C107 C108 C109 C110 -176.1(3) . . . . ?
C108 C109 C110 C111 1.2(5) . . . . ?
C109 C110 C111 C112 -2.9(5) . . . . ?
C110 C111 C112 C113 1.1(5) . . . . ?
C111 C112 C113 C108 2.5(4) . . . . ?
C111 C112 C113 C114 179.3(3) . . . . ?
C109 C108 C113 C112 -4.1(4) . . . . ?
C107 C108 C113 C112 174.4(3) . . . . ?
C109 C108 C113 C114 178.9(3) . . . . ?
C107 C108 C113 C114 -2.6(4) . . . . ?
C201 N1 C114 C101 -158.3(2) . . . . ?
B1 N1 C114 C101 4.2(3) . . . . ?
C201 N1 C114 C113 22.3(4) . . . . ?
B1 N1 C114 C113 -175.2(3) . . . . ?
O1 C101 C114 N1 -1.8(3) . . . . ?
C102 C101 C114 N1 177.3(2) . . . . ?
O1 C101 C114 C113 177.6(2) . . . . ?
C102 C101 C114 C113 -3.3(4) . . . . ?
C112 C113 C114 N1 7.8(5) . . . . ?
C108 C113 C114 N1 -175.3(3) . . . . ?
C112 C113 C114 C101 -171.5(3) . . . . ?
C108 C113 C114 C101 5.4(4) . . . . ?
C114 N1 C201 C202 -115.6(3) . . . . ?
B1 N1 C201 C202 85.2(3) . . . . ?
C114 N1 C201 C206 64.8(3) . . . . ?
B1 N1 C201 C206 -94.4(3) . . . . ?
C206 C201 C202 C203 1.2(4) . . . . ?
N1 C201 C202 C203 -178.4(2) . . . . ?
C206 C201 C202 C1 -176.9(3) . . . . ?
N1 C201 C202 C1 3.5(4) . . . . ?
C201 C202 C203 C204 -1.1(4) . . . . ?
C1 C202 C203 C204 177.1(3) . . . . ?
C202 C203 C204 C205 0.4(5) . . . . ?
C203 C204 C205 C206 0.2(5) . . . . ?
C204 C205 C206 C201 -0.1(4) . . . . ?
C204 C205 C206 C2 -179.5(3) . . . . ?
C202 C201 C206 C205 -0.6(4) . . . . ?
N1 C201 C206 C205 179.0(2) . . . . ?
C202 C201 C206 C2 178.7(3) . . . . ?
N1 C201 C206 C2 -1.6(4) . . . . ?
O1 B1 C301 C306 -116.7(3) . . . . ?
N1 B1 C301 C306 135.9(3) . . . . ?
C401 B1 C301 C306 6.9(4) . . . . ?
O1 B1 C301 C302 56.0(3) . . . . ?
N1 B1 C301 C302 -51.4(3) . . . . ?
C401 B1 C301 C302 179.6(2) . . . . ?
C306 C301 C302 F302 -179.9(2) . . . . ?
B1 C301 C302 F302 6.4(4) . . . . ?
C306 C301 C302 C303 -0.3(4) . . . . ?
B1 C301 C302 C303 -173.9(3) . . . . ?
F302 C302 C303 F303 0.4(4) . . . . ?
C301 C302 C303 F303 -179.2(3) . . . . ?
F302 C302 C303 C304 -179.1(3) . . . . ?
C301 C302 C303 C304 1.2(5) . . . . ?
F303 C303 C304 F304 0.5(5) . . . . ?
C302 C303 C304 F304 -180.0(3) . . . . ?
F303 C303 C304 C305 179.3(3) . . . . ?
C302 C303 C304 C305 -1.1(5) . . . . ?
F304 C304 C305 F305 -0.7(5) . . . . ?
C303 C304 C305 F305 -179.5(3) . . . . ?
F304 C304 C305 C306 179.0(3) . . . . ?
C303 C304 C305 C306 0.2(5) . . . . ?
F305 C305 C306 F306 0.2(4) . . . . ?
C304 C305 C306 F306 -179.5(3) . . . . ?
F305 C305 C306 C301 -179.5(3) . . . . ?
C304 C305 C306 C301 0.8(5) . . . . ?
C302 C301 C306 F306 179.6(3) . . . . ?
B1 C301 C306 F306 -7.4(4) . . . . ?
C302 C301 C306 C305 -0.7(4) . . . . ?
B1 C301 C306 C305 172.4(3) . . . . ?
O1 B1 C401 C406 -0.2(4) . . . . ?
N1 B1 C401 C406 108.6(3) . . . . ?
C301 B1 C401 C406 -120.1(3) . . . . ?
O1 B1 C401 C402 -178.8(2) . . . . ?
N1 B1 C401 C402 -70.0(3) . . . . ?
C301 B1 C401 C402 61.3(3) . . . . ?
C406 C401 C402 F402 177.3(2) . . . . ?
B1 C401 C402 F402 -3.9(4) . . . . ?
C406 C401 C402 C403 -0.5(4) . . . . ?
B1 C401 C402 C403 178.3(3) . . . . ?
F402 C402 C403 F403 2.5(4) . . . . ?
C401 C402 C403 F403 -179.7(3) . . . . ?
F402 C402 C403 C404 -177.6(3) . . . . ?
C401 C402 C403 C404 0.3(5) . . . . ?
F403 C403 C404 F404 0.3(4) . . . . ?
C402 C403 C404 F404 -179.6(3) . . . . ?
F403 C403 C404 C405 -179.9(3) . . . . ?
C402 C403 C404 C405 0.2(5) . . . . ?
F404 C404 C405 F405 -0.4(4) . . . . ?
C403 C404 C405 F405 179.8(3) . . . . ?
F404 C404 C405 C406 179.4(3) . . . . ?
C403 C404 C405 C406 -0.3(5) . . . . ?
F405 C405 C406 F406 0.6(4) . . . . ?
C404 C405 C406 F406 -179.2(3) . . . . ?
F405 C405 C406 C401 179.9(3) . . . . ?
C404 C405 C406 C401 0.1(5) . . . . ?
C402 C401 C406 F406 179.6(2) . . . . ?
B1 C401 C406 F406 0.9(4) . . . . ?
C402 C401 C406 C405 0.3(4) . . . . ?
B1 C401 C406 C405 -178.4(3) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_compound_06
_database_code_depnum_ccdc_archive 'CCDC 1535316'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9350(9)
_cell_length_b                   9.8367(11)
_cell_length_c                   20.542(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.585(5)
_cell_angle_gamma                90
_cell_volume                     1589.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2634
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.38

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13959
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3617
_reflns_number_gt                2427
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0613P)²+0.3151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_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
O1 O 0.12502(16) -0.12010(12) 0.07841(6) 0.0278(3) Uani 1 1 d D . . . .
H1O H 0.180(2) -0.0962(19) 0.0476(8) 0.033 Uiso 1 1 d D U . . .
N1 N 0.23072(18) 0.11958(14) 0.03125(7) 0.0215(3) Uani 1 1 d D . . . .
H1N H 0.153(2) 0.1408(18) -0.0031(8) 0.026 Uiso 1 1 d D U . . .
C2 C 0.5276(2) 0.02677(18) 0.12051(9) 0.0305(4) Uani 1 1 d . . . . .
H2A H 0.4625 0.0568 0.1552 0.046 Uiso 1 1 calc R U . . .
H2B H 0.6431 0.0023 0.1399 0.046 Uiso 1 1 calc R U . . .
H2C H 0.4720 -0.0526 0.0982 0.046 Uiso 1 1 calc R U . . .
C1 C 0.2592(2) 0.3207(2) -0.06882(9) 0.0363(5) Uani 1 1 d . . . . .
H1A H 0.2891 0.4005 -0.0935 0.054 Uiso 1 1 calc R U . . .
H1B H 0.1627 0.3427 -0.0455 0.054 Uiso 1 1 calc R U . . .
H1C H 0.2282 0.2454 -0.0993 0.054 Uiso 1 1 calc R U . . .
C101 C 0.1086(2) -0.00320(16) 0.11351(8) 0.0200(4) Uani 1 1 d . . . . .
C102 C 0.04147(19) -0.01891(16) 0.17461(8) 0.0197(4) Uani 1 1 d . . . . .
C103 C 0.0015(2) -0.14864(17) 0.19769(8) 0.0248(4) Uani 1 1 d . . . . .
H103 H 0.0213 -0.2272 0.1729 0.030 Uiso 1 1 calc R U . . .
C104 C -0.0655(2) -0.16249(18) 0.25539(9) 0.0297(4) Uani 1 1 d . . . . .
H104 H -0.0929 -0.2502 0.2703 0.036 Uiso 1 1 calc R U . . .
C105 C -0.0935(2) -0.04737(19) 0.29232(9) 0.0303(4) Uani 1 1 d . . . . .
H105 H -0.1416 -0.0569 0.3320 0.036 Uiso 1 1 calc R U . . .
C106 C -0.0519(2) 0.07966(18) 0.27153(8) 0.0267(4) Uani 1 1 d . . . . .
H106 H -0.0709 0.1568 0.2974 0.032 Uiso 1 1 calc R U . . .
C107 C 0.0186(2) 0.09795(16) 0.21243(8) 0.0203(4) Uani 1 1 d . . . . .
C108 C 0.0670(2) 0.23062(16) 0.18950(8) 0.0200(4) Uani 1 1 d . . . . .
C109 C 0.0451(2) 0.35092(17) 0.22488(9) 0.0266(4) Uani 1 1 d . . . . .
H109 H 0.0006 0.3455 0.2655 0.032 Uiso 1 1 calc R U . . .
C110 C 0.0869(2) 0.47587(18) 0.20161(9) 0.0301(4) Uani 1 1 d . . . . .
H110 H 0.0732 0.5553 0.2267 0.036 Uiso 1 1 calc R U . . .
C111 C 0.1494(2) 0.48663(17) 0.14143(9) 0.0287(4) Uani 1 1 d . . . . .
H111 H 0.1740 0.5735 0.1248 0.034 Uiso 1 1 calc R U . . .
C112 C 0.1753(2) 0.37118(16) 0.10624(8) 0.0229(4) Uani 1 1 d . . . . .
H112 H 0.2202 0.3791 0.0658 0.027 Uiso 1 1 calc R U . . .
C113 C 0.13622(19) 0.24072(16) 0.12927(8) 0.0190(4) Uani 1 1 d . . . . .
C114 C 0.1584(2) 0.11907(16) 0.09209(8) 0.0193(4) Uani 1 1 d . . . . .
C201 C 0.3923(2) 0.18127(16) 0.02820(8) 0.0200(4) Uani 1 1 d . . . . .
C202 C 0.4088(2) 0.27999(17) -0.02016(8) 0.0246(4) Uani 1 1 d . . . . .
C203 C 0.5671(2) 0.33973(18) -0.02274(9) 0.0298(4) Uani 1 1 d . . . . .
H203 H 0.5792 0.4060 -0.0554 0.036 Uiso 1 1 calc R U . . .
C204 C 0.7068(2) 0.30418(19) 0.02141(10) 0.0317(4) Uani 1 1 d . . . . .
H204 H 0.8131 0.3477 0.0199 0.038 Uiso 1 1 calc R U . . .
C205 C 0.6905(2) 0.20471(18) 0.06779(9) 0.0292(4) Uani 1 1 d . . . . .
H205 H 0.7872 0.1796 0.0977 0.035 Uiso 1 1 calc R U . . .
C206 C 0.5355(2) 0.14037(17) 0.07160(8) 0.0234(4) 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
O1 C101 1.3725(18) . ?
O1 H1O 0.848(15) . ?
N1 C201 1.427(2) . ?
N1 C114 1.443(2) . ?
N1 H1N 0.899(14) . ?
C2 C206 1.509(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 C202 1.502(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C101 C114 1.357(2) . ?
C101 C102 1.435(2) . ?
C102 C103 1.412(2) . ?
C102 C107 1.413(2) . ?
C103 C104 1.368(2) . ?
C103 H103 0.9500 . ?
C104 C105 1.397(2) . ?
C104 H104 0.9500 . ?
C105 C106 1.375(2) . ?
C105 H105 0.9500 . ?
C106 C107 1.413(2) . ?
C106 H106 0.9500 . ?
C107 C108 1.456(2) . ?
C108 C109 1.411(2) . ?
C108 C113 1.422(2) . ?
C109 C110 1.375(2) . ?
C109 H109 0.9500 . ?
C110 C111 1.395(3) . ?
C110 H110 0.9500 . ?
C111 C112 1.376(2) . ?
C111 H111 0.9500 . ?
C112 C113 1.416(2) . ?
C112 H112 0.9500 . ?
C113 C114 1.443(2) . ?
C201 C206 1.407(2) . ?
C201 C202 1.408(2) . ?
C202 C203 1.394(2) . ?
C203 C204 1.381(3) . ?
C203 H203 0.9500 . ?
C204 C205 1.384(3) . ?
C204 H204 0.9500 . ?
C205 C206 1.395(2) . ?
C205 H205 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C101 O1 H1O 104.7(13) . . ?
C201 N1 C114 120.12(13) . . ?
C201 N1 H1N 113.4(11) . . ?
C114 N1 H1N 111.6(11) . . ?
C206 C2 H2A 109.5 . . ?
C206 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C206 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C202 C1 H1A 109.5 . . ?
C202 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C202 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C114 C101 O1 121.36(14) . . ?
C114 C101 C102 122.44(14) . . ?
O1 C101 C102 116.17(14) . . ?
C103 C102 C107 120.00(15) . . ?
C103 C102 C101 121.11(14) . . ?
C107 C102 C101 118.88(14) . . ?
C104 C103 C102 120.73(16) . . ?
C104 C103 H103 119.6 . . ?
C102 C103 H103 119.6 . . ?
C103 C104 C105 119.84(16) . . ?
C103 C104 H104 120.1 . . ?
C105 C104 H104 120.1 . . ?
C106 C105 C104 120.39(16) . . ?
C106 C105 H105 119.8 . . ?
C104 C105 H105 119.8 . . ?
C105 C106 C107 121.40(16) . . ?
C105 C106 H106 119.3 . . ?
C107 C106 H106 119.3 . . ?
C102 C107 C106 117.58(15) . . ?
C102 C107 C108 119.52(14) . . ?
C106 C107 C108 122.90(15) . . ?
C109 C108 C113 118.52(14) . . ?
C109 C108 C107 121.93(14) . . ?
C113 C108 C107 119.54(14) . . ?
C110 C109 C108 121.23(16) . . ?
C110 C109 H109 119.4 . . ?
C108 C109 H109 119.4 . . ?
C109 C110 C111 120.40(16) . . ?
C109 C110 H110 119.8 . . ?
C111 C110 H110 119.8 . . ?
C112 C111 C110 119.86(16) . . ?
C112 C111 H111 120.1 . . ?
C110 C111 H111 120.1 . . ?
C111 C112 C113 121.19(15) . . ?
C111 C112 H112 119.4 . . ?
C113 C112 H112 119.4 . . ?
C112 C113 C108 118.74(14) . . ?
C112 C113 C114 121.83(14) . . ?
C108 C113 C114 119.39(14) . . ?
C101 C114 N1 116.74(14) . . ?
C101 C114 C113 120.16(14) . . ?
N1 C114 C113 123.09(14) . . ?
C206 C201 C202 120.11(15) . . ?
C206 C201 N1 120.36(15) . . ?
C202 C201 N1 119.48(14) . . ?
C203 C202 C201 119.08(16) . . ?
C203 C202 C1 119.96(16) . . ?
C201 C202 C1 120.96(15) . . ?
C204 C203 C202 121.14(17) . . ?
C204 C203 H203 119.4 . . ?
C202 C203 H203 119.4 . . ?
C203 C204 C205 119.46(16) . . ?
C203 C204 H204 120.3 . . ?
C205 C204 H204 120.3 . . ?
C204 C205 C206 121.50(17) . . ?
C204 C205 H205 119.2 . . ?
C206 C205 H205 119.2 . . ?
C205 C206 C201 118.62(16) . . ?
C205 C206 C2 119.18(16) . . ?
C201 C206 C2 122.17(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
C114 C101 C102 C103 -175.70(15) . . . . ?
O1 C101 C102 C103 2.4(2) . . . . ?
C114 C101 C102 C107 3.1(2) . . . . ?
O1 C101 C102 C107 -178.83(14) . . . . ?
C107 C102 C103 C104 2.4(2) . . . . ?
C101 C102 C103 C104 -178.76(15) . . . . ?
C102 C103 C104 C105 -0.5(3) . . . . ?
C103 C104 C105 C106 -1.0(3) . . . . ?
C104 C105 C106 C107 0.5(3) . . . . ?
C103 C102 C107 C106 -2.8(2) . . . . ?
C101 C102 C107 C106 178.40(15) . . . . ?
C103 C102 C107 C108 177.39(15) . . . . ?
C101 C102 C107 C108 -1.4(2) . . . . ?
C105 C106 C107 C102 1.3(3) . . . . ?
C105 C106 C107 C108 -178.84(16) . . . . ?
C102 C107 C108 C109 179.22(15) . . . . ?
C106 C107 C108 C109 -0.6(3) . . . . ?
C102 C107 C108 C113 0.2(2) . . . . ?
C106 C107 C108 C113 -179.62(15) . . . . ?
C113 C108 C109 C110 0.9(2) . . . . ?
C107 C108 C109 C110 -178.08(16) . . . . ?
C108 C109 C110 C111 1.2(3) . . . . ?
C109 C110 C111 C112 -2.4(3) . . . . ?
C110 C111 C112 C113 1.4(3) . . . . ?
C111 C112 C113 C108 0.8(2) . . . . ?
C111 C112 C113 C114 178.30(15) . . . . ?
C109 C108 C113 C112 -1.9(2) . . . . ?
C107 C108 C113 C112 177.12(14) . . . . ?
C109 C108 C113 C114 -179.49(15) . . . . ?
C107 C108 C113 C114 -0.4(2) . . . . ?
O1 C101 C114 N1 -0.7(2) . . . . ?
C102 C101 C114 N1 177.28(14) . . . . ?
O1 C101 C114 C113 178.64(14) . . . . ?
C102 C101 C114 C113 -3.4(2) . . . . ?
C201 N1 C114 C101 -127.16(16) . . . . ?
C201 N1 C114 C113 53.5(2) . . . . ?
C112 C113 C114 C101 -175.46(15) . . . . ?
C108 C113 C114 C101 2.0(2) . . . . ?
C112 C113 C114 N1 3.8(2) . . . . ?
C108 C113 C114 N1 -178.70(14) . . . . ?
C114 N1 C201 C206 55.5(2) . . . . ?
C114 N1 C201 C202 -126.86(16) . . . . ?
C206 C201 C202 C203 -2.3(2) . . . . ?
N1 C201 C202 C203 179.99(14) . . . . ?
C206 C201 C202 C1 177.32(16) . . . . ?
N1 C201 C202 C1 -0.4(2) . . . . ?
C201 C202 C203 C204 -0.4(3) . . . . ?
C1 C202 C203 C204 179.99(17) . . . . ?
C202 C203 C204 C205 1.9(3) . . . . ?
C203 C204 C205 C206 -0.8(3) . . . . ?
C204 C205 C206 C201 -1.8(3) . . . . ?
C204 C205 C206 C2 176.38(16) . . . . ?
C202 C201 C206 C205 3.4(2) . . . . ?
N1 C201 C206 C205 -178.96(14) . . . . ?
C202 C201 C206 C2 -174.77(16) . . . . ?
N1 C201 C206 C2 2.9(2) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_compound_18
_database_code_depnum_ccdc_archive 'CCDC 1535318'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C40 H22 B F10 N2'
_chemical_formula_weight         731.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   9.508(4)
_cell_length_b                   21.381(8)
_cell_length_c                   15.841(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3220(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    587
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      14.63

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             1484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4833
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14156
_diffrn_reflns_av_unetI/netI     0.1262
_diffrn_reflns_av_R_equivalents  0.2099
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         20.000
_diffrn_reflns_theta_full        20.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1507
_reflns_number_gt                861
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0919P)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         1507
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1971
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
B01 B 0.0000 0.1775(6) 0.2500 0.029(4) Uani 1 2 d S T P . .
N01 N 0.0561(7) 0.2264(3) 0.3163(4) 0.0303(19) Uani 1 1 d . . . . .
F302 F 0.3036(5) 0.2099(2) 0.2312(3) 0.0496(14) Uani 1 1 d . . . . .
F303 F 0.4943(7) 0.1438(3) 0.1479(3) 0.0688(17) Uani 1 1 d . . . . .
F304 F 0.4257(6) 0.0374(3) 0.0665(3) 0.0712(19) Uani 1 1 d . . . . .
F305 F 0.1561(6) -0.0051(2) 0.0740(3) 0.0708(19) Uani 1 1 d . . . . .
F306 F -0.0356(6) 0.0552(2) 0.1629(3) 0.0492(15) Uani 1 1 d . . . . .
C01 C 0.1519(11) 0.1450(4) 0.6572(5) 0.066(3) Uani 1 1 d . . . . .
H01A H 0.1317 0.1786 0.6976 0.098 Uiso 1 1 calc R U . . .
H01B H 0.2491 0.1308 0.6648 0.098 Uiso 1 1 calc R U . . .
H01C H 0.0874 0.1100 0.6670 0.098 Uiso 1 1 calc R U . . .
C101 C 0.0370(8) 0.2863(4) 0.2892(5) 0.031(2) Uani 1 1 d . . . . .
C102 C 0.0937(9) 0.3435(4) 0.3227(5) 0.034(2) Uani 1 1 d . . . . .
C103 C 0.2013(9) 0.3453(4) 0.3844(5) 0.041(2) Uani 1 1 d . . . . .
H103 H 0.2309 0.3074 0.4102 0.050 Uiso 1 1 calc R U . . .
C104 C 0.2643(10) 0.4008(5) 0.4079(6) 0.048(3) Uani 1 1 d . . . . .
H104 H 0.3371 0.4009 0.4490 0.058 Uiso 1 1 calc R U . . .
C105 C 0.2206(12) 0.4561(5) 0.3711(7) 0.056(3) Uani 1 1 d . . . . .
H105 H 0.2628 0.4945 0.3876 0.068 Uiso 1 1 calc R U . . .
C106 C 0.1180(12) 0.4560(4) 0.3117(6) 0.052(3) Uani 1 1 d . . . . .
H106 H 0.0895 0.4948 0.2881 0.062 Uiso 1 1 calc R U . . .
C107 C 0.0519(9) 0.4009(4) 0.2836(5) 0.039(2) Uani 1 1 d . . . . .
C201 C 0.0853(9) 0.2085(4) 0.4015(5) 0.026(2) Uani 1 1 d . . . . .
C202 C 0.0095(9) 0.2357(4) 0.4669(6) 0.037(2) Uani 1 1 d . . . . .
H202 H -0.0587 0.2671 0.4559 0.044 Uiso 1 1 calc R U . . .
C203 C 0.0356(10) 0.2159(4) 0.5485(5) 0.043(3) Uani 1 1 d . . . . .
H203 H -0.0150 0.2349 0.5934 0.051 Uiso 1 1 calc R U . . .
C204 C 0.1327(10) 0.1694(4) 0.5676(6) 0.043(3) Uani 1 1 d . . . . .
C205 C 0.2083(9) 0.1432(4) 0.5016(6) 0.039(2) Uani 1 1 d . . . . .
H205 H 0.2761 0.1116 0.5127 0.047 Uiso 1 1 calc R U . . .
C206 C 0.1849(9) 0.1631(4) 0.4191(5) 0.032(2) Uani 1 1 d . . . . .
H206 H 0.2379 0.1454 0.3743 0.039 Uiso 1 1 calc R U . . .
C301 C 0.1222(10) 0.1347(4) 0.2032(5) 0.030(2) Uani 1 1 d . . . . .
C302 C 0.2608(11) 0.1543(4) 0.1946(5) 0.042(2) Uani 1 1 d . . . . .
C303 C 0.3625(10) 0.1210(5) 0.1510(6) 0.048(3) Uani 1 1 d . . . . .
C304 C 0.3247(14) 0.0667(5) 0.1111(5) 0.051(3) Uani 1 1 d . . . . .
C305 C 0.1902(12) 0.0475(5) 0.1149(6) 0.044(3) Uani 1 1 d . . . . .
C306 C 0.0952(10) 0.0798(4) 0.1606(5) 0.034(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B01 N01 1.574(11) 4 ?
B01 N01 1.574(11) . ?
B01 C301 1.654(11) 4 ?
B01 C301 1.654(11) . ?
N01 C101 1.363(10) . ?
N01 C201 1.430(9) . ?
F302 C302 1.383(10) . ?
F303 C303 1.346(10) . ?
F304 C304 1.346(10) . ?
F305 C305 1.339(10) . ?
F306 C306 1.350(9) . ?
C01 C204 1.523(12) . ?
C101 C101 1.428(16) 4 ?
C101 C102 1.440(11) . ?
C102 C103 1.415(12) . ?
C102 C107 1.431(11) . ?
C103 C104 1.379(11) . ?
C104 C105 1.383(13) . ?
C105 C106 1.355(13) . ?
C106 C107 1.408(12) . ?
C107 C107 1.452(16) 4 ?
C201 C206 1.384(10) . ?
C201 C202 1.390(11) . ?
C202 C203 1.381(11) . ?
C203 C204 1.390(12) . ?
C204 C205 1.388(12) . ?
C205 C206 1.393(11) . ?
C301 C306 1.379(11) . ?
C301 C302 1.389(12) . ?
C302 C303 1.386(13) . ?
C303 C304 1.370(13) . ?
C304 C305 1.345(13) . ?
C305 C306 1.347(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N01 B01 N01 96.9(9) 4 . ?
N01 B01 C301 115.3(4) 4 4 ?
N01 B01 C301 107.8(3) . 4 ?
N01 B01 C301 107.8(3) 4 . ?
N01 B01 C301 115.3(4) . . ?
C301 B01 C301 112.8(10) 4 . ?
C101 N01 C201 125.0(6) . . ?
C101 N01 B01 111.6(6) . . ?
C201 N01 B01 121.3(6) . . ?
N01 C101 C101 109.8(4) . 4 ?
N01 C101 C102 129.3(7) . . ?
C101 C101 C102 120.3(5) 4 . ?
C103 C102 C107 118.5(8) . . ?
C103 C102 C101 123.2(8) . . ?
C107 C102 C101 117.8(8) . . ?
C104 C103 C102 121.6(9) . . ?
C103 C104 C105 119.4(9) . . ?
C106 C105 C104 120.5(9) . . ?
C105 C106 C107 122.8(10) . . ?
C106 C107 C102 117.1(8) . . ?
C106 C107 C107 122.4(6) . 4 ?
C102 C107 C107 120.4(5) . 4 ?
C206 C201 C202 119.8(7) . . ?
C206 C201 N01 120.6(7) . . ?
C202 C201 N01 119.5(8) . . ?
C203 C202 C201 118.5(8) . . ?
C202 C203 C204 122.8(8) . . ?
C205 C204 C203 117.9(8) . . ?
C205 C204 C01 120.1(9) . . ?
C203 C204 C01 121.9(9) . . ?
C204 C205 C206 120.0(9) . . ?
C201 C206 C205 120.9(8) . . ?
C306 C301 C302 112.7(8) . . ?
C306 C301 B01 124.1(8) . . ?
C302 C301 B01 122.9(8) . . ?
F302 C302 C303 116.4(9) . . ?
F302 C302 C301 119.8(9) . . ?
C303 C302 C301 123.7(9) . . ?
F303 C303 C304 122.3(10) . . ?
F303 C303 C302 118.8(11) . . ?
C304 C303 C302 118.9(10) . . ?
C305 C304 F304 124.1(11) . . ?
C305 C304 C303 119.1(9) . . ?
F304 C304 C303 116.7(12) . . ?
F305 C305 C304 117.7(9) . . ?
F305 C305 C306 121.9(10) . . ?
C304 C305 C306 120.4(10) . . ?
C305 C306 F306 115.6(9) . . ?
C305 C306 C301 125.1(9) . . ?
F306 C306 C301 119.3(9) . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_compound_03
_database_code_depnum_ccdc_archive 'CCDC 1535312'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C34 H18 B F10 N O'
_chemical_formula_weight         657.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.7684(15)
_cell_length_b                   14.767(3)
_cell_length_c                   19.986(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.712(6)
_cell_angle_gamma                90
_cell_volume                     2800.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1114
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      19.76

_exptl_crystal_description       prism
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21191
_diffrn_reflns_av_unetI/netI     0.1203
_diffrn_reflns_av_R_equivalents  0.1245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.733
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4943
_reflns_number_gt                2679
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0636P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4943
_refine_ls_number_parameters     429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
F305 F 1.2022(2) 0.75987(18) 0.35981(14) 0.0413(7) Uani 1 1 d . . . . .
F404 F 1.0411(3) 0.28348(18) 0.49227(13) 0.0410(7) Uani 1 1 d . . . . .
N1 N 0.6005(3) 0.5629(2) 0.29465(17) 0.0165(8) Uani 1 1 d . . . . .
H1N H 0.581(4) 0.615(3) 0.3175(19) 0.020 Uiso 1 1 d . U . . .
C302 C 0.7788(4) 0.7440(3) 0.3359(2) 0.0198(10) Uani 1 1 d . . . . .
C301 C 0.8461(4) 0.6638(3) 0.32640(19) 0.0169(9) Uani 1 1 d . . . . .
C401 C 0.8538(4) 0.4839(3) 0.3521(2) 0.0179(9) Uani 1 1 d . . . . .
C306 C 0.9906(4) 0.6750(3) 0.3345(2) 0.0191(10) Uani 1 1 d . . . . .
C303 C 0.8443(4) 0.8258(3) 0.3522(2) 0.0201(10) Uani 1 1 d . . . . .
C406 C 0.9377(4) 0.4157(3) 0.3354(2) 0.0203(10) Uani 1 1 d . . . . .
C304 C 0.9879(4) 0.8322(3) 0.3614(2) 0.0244(10) Uani 1 1 d . . . . .
C402 C 0.8407(4) 0.4798(3) 0.4196(2) 0.0208(10) Uani 1 1 d . . . . .
C403 C 0.8977(4) 0.4138(3) 0.4667(2) 0.0223(10) Uani 1 1 d . . . . .
F402 F 0.7689(2) 0.54719(16) 0.44354(11) 0.0253(6) Uani 1 1 d . . . . .
B1 B 0.7780(5) 0.5636(3) 0.3017(2) 0.0182(11) Uani 1 1 d . . . . .
F302 F 0.6364(2) 0.74439(16) 0.32948(13) 0.0300(6) Uani 1 1 d . . . . .
F306 F 1.0692(2) 0.60216(16) 0.32487(12) 0.0262(6) Uani 1 1 d . . . . .
F303 F 0.7699(2) 0.90064(17) 0.35931(13) 0.0324(6) Uani 1 1 d . . . . .
F406 F 0.9631(2) 0.41197(17) 0.27186(12) 0.0298(6) Uani 1 1 d . . . . .
F304 F 1.0558(3) 0.91040(17) 0.37924(14) 0.0393(7) Uani 1 1 d . . . . .
F405 F 1.0811(2) 0.28453(17) 0.36129(13) 0.0369(7) Uani 1 1 d . . . . .
F403 F 0.8754(2) 0.41328(18) 0.53057(12) 0.0357(7) Uani 1 1 d . . . . .
O1 O 0.7831(2) 0.55245(18) 0.22886(13) 0.0172(7) Uani 1 1 d . . . . .
C405 C 0.9999(4) 0.3488(3) 0.3812(2) 0.0251(11) Uani 1 1 d . . . . .
C305 C 1.0611(4) 0.7553(3) 0.3520(2) 0.0236(10) Uani 1 1 d . . . . .
C404 C 0.9793(4) 0.3479(3) 0.4472(2) 0.0261(11) Uani 1 1 d . . . . .
C101 C 0.6551(4) 0.5733(3) 0.18834(19) 0.0150(9) Uani 1 1 d . . . . .
C102 C 0.6349(4) 0.5873(3) 0.11596(19) 0.0161(9) Uani 1 1 d . . . . .
C103 C 0.7478(4) 0.5826(3) 0.0835(2) 0.0196(10) Uani 1 1 d . . . . .
H103 H 0.8398 0.5687 0.1098 0.023 Uiso 1 1 calc R U . . .
C104 C 0.7260(4) 0.5979(3) 0.0141(2) 0.0270(11) Uani 1 1 d . . . . .
H104 H 0.8025 0.5948 -0.0076 0.032 Uiso 1 1 calc R U . . .
C105 C 0.5910(4) 0.6182(3) -0.0244(2) 0.0287(11) Uani 1 1 d . . . . .
H105 H 0.5761 0.6297 -0.0723 0.034 Uiso 1 1 calc R U . . .
C106 C 0.4795(4) 0.6219(3) 0.0061(2) 0.0260(11) Uani 1 1 d . . . . .
H106 H 0.3882 0.6353 -0.0213 0.031 Uiso 1 1 calc R U . . .
C107 C 0.4970(4) 0.6063(3) 0.0771(2) 0.0190(10) Uani 1 1 d . . . . .
C108 C 0.3807(4) 0.6086(3) 0.1115(2) 0.0165(9) Uani 1 1 d . . . . .
C109 C 0.2413(4) 0.6234(3) 0.0741(2) 0.0231(10) Uani 1 1 d . . . . .
H109 H 0.2226 0.6322 0.0257 0.028 Uiso 1 1 calc R U . . .
C110 C 0.1312(4) 0.6255(3) 0.1065(2) 0.0271(11) Uani 1 1 d . . . . .
H110 H 0.0380 0.6358 0.0801 0.033 Uiso 1 1 calc R U . . .
C111 C 0.1554(4) 0.6127(3) 0.1773(2) 0.0248(11) Uani 1 1 d . . . . .
H111 H 0.0791 0.6148 0.1993 0.030 Uiso 1 1 calc R U . . .
C112 C 0.2906(4) 0.5971(3) 0.2155(2) 0.0193(10) Uani 1 1 d . . . . .
H112 H 0.3069 0.5879 0.2637 0.023 Uiso 1 1 calc R U . . .
C113 C 0.4050(4) 0.5945(3) 0.18370(19) 0.0155(9) Uani 1 1 d . . . . .
C114 C 0.5480(4) 0.5781(3) 0.21989(19) 0.0148(9) Uani 1 1 d . . . . .
C201 C 0.5334(4) 0.4888(3) 0.3256(2) 0.0186(10) Uani 1 1 d . . . . .
C206 C 0.5363(4) 0.3998(3) 0.3018(2) 0.0198(10) Uani 1 1 d . . . . .
C205 C 0.4734(4) 0.3333(3) 0.3341(2) 0.0277(11) Uani 1 1 d . . . . .
H205 H 0.4742 0.2724 0.3190 0.033 Uiso 1 1 calc R U . . .
C204 C 0.4100(4) 0.3531(4) 0.3872(2) 0.0380(13) Uani 1 1 d . . . . .
H204 H 0.3696 0.3064 0.4090 0.046 Uiso 1 1 calc R U . . .
C203 C 0.4065(4) 0.4423(3) 0.4082(2) 0.0305(12) Uani 1 1 d . . . . .
H203 H 0.3608 0.4561 0.4439 0.037 Uiso 1 1 calc R U . . .
C202 C 0.4679(4) 0.5125(3) 0.3787(2) 0.0225(10) Uani 1 1 d . . . . .
C1 C 0.4604(4) 0.6082(3) 0.4039(2) 0.0306(12) Uani 1 1 d . . . . .
H1A H 0.4070 0.6091 0.4397 0.046 Uiso 1 1 calc R U . . .
H1B H 0.4135 0.6468 0.3654 0.046 Uiso 1 1 calc R U . . .
H1C H 0.5560 0.6308 0.4231 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6005(4) 0.3718(3) 0.2432(2) 0.0247(10) Uani 1 1 d . . . . .
H2A H 0.5331 0.3833 0.1993 0.037 Uiso 1 1 calc R U . . .
H2B H 0.6233 0.3071 0.2472 0.037 Uiso 1 1 calc R U . . .
H2C H 0.6866 0.4068 0.2453 0.037 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
F305 C305 1.352(4) . ?
F404 C404 1.350(5) . ?
N1 C114 1.477(5) . ?
N1 C201 1.484(5) . ?
N1 B1 1.706(5) . ?
N1 H1N 0.93(4) . ?
C302 F302 1.367(4) . ?
C302 C303 1.370(6) . ?
C302 C301 1.389(6) . ?
C301 C306 1.391(5) . ?
C301 B1 1.649(6) . ?
C401 C402 1.387(5) . ?
C401 C406 1.388(5) . ?
C401 B1 1.611(6) . ?
C306 F306 1.361(4) . ?
C306 C305 1.375(6) . ?
C303 F303 1.349(4) . ?
C303 C304 1.374(6) . ?
C406 F406 1.351(4) . ?
C406 C405 1.387(6) . ?
C304 F304 1.336(5) . ?
C304 C305 1.378(6) . ?
C402 F402 1.367(4) . ?
C402 C403 1.378(6) . ?
C403 F403 1.345(4) . ?
C403 C404 1.372(6) . ?
B1 O1 1.478(5) . ?
F405 C405 1.356(5) . ?
O1 C101 1.354(4) . ?
C405 C404 1.380(6) . ?
C101 C114 1.345(5) . ?
C101 C102 1.428(5) . ?
C102 C103 1.408(5) . ?
C102 C107 1.414(5) . ?
C103 C104 1.371(5) . ?
C103 H103 0.9500 . ?
C104 C105 1.392(6) . ?
C104 H104 0.9500 . ?
C105 C106 1.370(5) . ?
C105 H105 0.9500 . ?
C106 C107 1.407(5) . ?
C106 H106 0.9500 . ?
C107 C108 1.461(5) . ?
C108 C109 1.407(5) . ?
C108 C113 1.421(5) . ?
C109 C110 1.381(5) . ?
C109 H109 0.9500 . ?
C110 C111 1.392(6) . ?
C110 H110 0.9500 . ?
C111 C112 1.379(5) . ?
C111 H111 0.9500 . ?
C112 C113 1.410(5) . ?
C112 H112 0.9500 . ?
C113 C114 1.433(5) . ?
C201 C206 1.399(6) . ?
C201 C202 1.408(5) . ?
C206 C205 1.395(6) . ?
C206 C2 1.511(5) . ?
C205 C204 1.382(6) . ?
C205 H205 0.9500 . ?
C204 C203 1.385(6) . ?
C204 H204 0.9500 . ?
C203 C202 1.397(6) . ?
C203 H203 0.9500 . ?
C202 C1 1.508(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C114 N1 C201 116.8(3) . . ?
C114 N1 B1 100.7(3) . . ?
C201 N1 B1 120.7(3) . . ?
C114 N1 H1N 108(2) . . ?
C201 N1 H1N 104(2) . . ?
B1 N1 H1N 106(2) . . ?
F302 C302 C303 115.2(4) . . ?
F302 C302 C301 119.7(4) . . ?
C303 C302 C301 125.1(4) . . ?
C302 C301 C306 112.5(4) . . ?
C302 C301 B1 129.4(3) . . ?
C306 C301 B1 117.9(3) . . ?
C402 C401 C406 113.5(4) . . ?
C402 C401 B1 120.4(3) . . ?
C406 C401 B1 126.1(4) . . ?
F306 C306 C305 116.9(3) . . ?
F306 C306 C301 118.7(4) . . ?
C305 C306 C301 124.4(4) . . ?
F303 C303 C302 121.0(4) . . ?
F303 C303 C304 119.2(4) . . ?
C302 C303 C304 119.8(4) . . ?
F406 C406 C405 116.3(4) . . ?
F406 C406 C401 120.5(4) . . ?
C405 C406 C401 123.3(4) . . ?
F304 C304 C303 121.4(4) . . ?
F304 C304 C305 120.5(4) . . ?
C303 C304 C305 118.1(4) . . ?
F402 C402 C403 115.7(4) . . ?
F402 C402 C401 118.8(4) . . ?
C403 C402 C401 125.4(4) . . ?
F403 C403 C404 120.1(4) . . ?
F403 C403 C402 121.5(4) . . ?
C404 C403 C402 118.4(4) . . ?
O1 B1 C401 114.7(3) . . ?
O1 B1 C301 106.8(3) . . ?
C401 B1 C301 112.0(3) . . ?
O1 B1 N1 100.9(3) . . ?
C401 B1 N1 110.8(3) . . ?
C301 B1 N1 111.1(3) . . ?
C101 O1 B1 108.8(3) . . ?
F405 C405 C404 120.1(4) . . ?
F405 C405 C406 120.0(4) . . ?
C404 C405 C406 119.9(4) . . ?
F305 C305 C306 120.5(4) . . ?
F305 C305 C304 119.4(4) . . ?
C306 C305 C304 120.1(4) . . ?
F404 C404 C403 120.6(4) . . ?
F404 C404 C405 120.0(4) . . ?
C403 C404 C405 119.4(4) . . ?
C114 C101 O1 116.2(3) . . ?
C114 C101 C102 122.1(3) . . ?
O1 C101 C102 121.7(3) . . ?
C103 C102 C107 120.3(4) . . ?
C103 C102 C101 121.6(3) . . ?
C107 C102 C101 118.0(3) . . ?
C104 C103 C102 120.5(4) . . ?
C104 C103 H103 119.8 . . ?
C102 C103 H103 119.8 . . ?
C103 C104 C105 119.6(4) . . ?
C103 C104 H104 120.2 . . ?
C105 C104 H104 120.2 . . ?
C106 C105 C104 120.7(4) . . ?
C106 C105 H105 119.6 . . ?
C104 C105 H105 119.6 . . ?
C105 C106 C107 121.5(4) . . ?
C105 C106 H106 119.2 . . ?
C107 C106 H106 119.2 . . ?
C106 C107 C102 117.3(3) . . ?
C106 C107 C108 123.3(4) . . ?
C102 C107 C108 119.5(3) . . ?
C109 C108 C113 118.1(3) . . ?
C109 C108 C107 121.1(4) . . ?
C113 C108 C107 120.9(3) . . ?
C110 C109 C108 121.2(4) . . ?
C110 C109 H109 119.4 . . ?
C108 C109 H109 119.4 . . ?
C109 C110 C111 120.7(4) . . ?
C109 C110 H110 119.6 . . ?
C111 C110 H110 119.6 . . ?
C112 C111 C110 119.6(4) . . ?
C112 C111 H111 120.2 . . ?
C110 C111 H111 120.2 . . ?
C111 C112 C113 120.9(4) . . ?
C111 C112 H112 119.6 . . ?
C113 C112 H112 119.6 . . ?
C112 C113 C108 119.6(3) . . ?
C112 C113 C114 124.0(3) . . ?
C108 C113 C114 116.4(3) . . ?
C101 C114 C113 123.1(4) . . ?
C101 C114 N1 110.1(3) . . ?
C113 C114 N1 126.8(3) . . ?
C206 C201 C202 122.6(4) . . ?
C206 C201 N1 120.4(3) . . ?
C202 C201 N1 117.0(4) . . ?
C205 C206 C201 117.2(4) . . ?
C205 C206 C2 118.3(4) . . ?
C201 C206 C2 124.4(4) . . ?
C204 C205 C206 122.3(4) . . ?
C204 C205 H205 118.9 . . ?
C206 C205 H205 118.9 . . ?
C205 C204 C203 118.8(4) . . ?
C205 C204 H204 120.6 . . ?
C203 C204 H204 120.6 . . ?
C204 C203 C202 122.3(4) . . ?
C204 C203 H203 118.9 . . ?
C202 C203 H203 118.9 . . ?
C203 C202 C201 116.8(4) . . ?
C203 C202 C1 119.6(4) . . ?
C201 C202 C1 123.6(4) . . ?
C202 C1 H1A 109.5 . . ?
C202 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C202 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C206 C2 H2A 109.5 . . ?
C206 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C206 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
F302 C302 C301 C306 179.8(3) . . . . ?
C303 C302 C301 C306 -0.7(6) . . . . ?
F302 C302 C301 B1 5.1(6) . . . . ?
C303 C302 C301 B1 -175.4(4) . . . . ?
C302 C301 C306 F306 -178.3(3) . . . . ?
B1 C301 C306 F306 -2.9(5) . . . . ?
C302 C301 C306 C305 1.8(6) . . . . ?
B1 C301 C306 C305 177.2(4) . . . . ?
F302 C302 C303 F303 -1.7(5) . . . . ?
C301 C302 C303 F303 178.8(4) . . . . ?
F302 C302 C303 C304 178.5(3) . . . . ?
C301 C302 C303 C304 -1.0(6) . . . . ?
C402 C401 C406 F406 -178.5(3) . . . . ?
B1 C401 C406 F406 0.3(6) . . . . ?
C402 C401 C406 C405 1.4(6) . . . . ?
B1 C401 C406 C405 -179.9(4) . . . . ?
F303 C303 C304 F304 2.0(6) . . . . ?
C302 C303 C304 F304 -178.2(4) . . . . ?
F303 C303 C304 C305 -178.2(4) . . . . ?
C302 C303 C304 C305 1.6(6) . . . . ?
C406 C401 C402 F402 175.4(3) . . . . ?
B1 C401 C402 F402 -3.5(5) . . . . ?
C406 C401 C402 C403 -2.8(6) . . . . ?
B1 C401 C402 C403 178.3(4) . . . . ?
F402 C402 C403 F403 4.3(6) . . . . ?
C401 C402 C403 F403 -177.5(4) . . . . ?
F402 C402 C403 C404 -175.5(3) . . . . ?
C401 C402 C403 C404 2.7(6) . . . . ?
C402 C401 B1 O1 -171.5(3) . . . . ?
C406 C401 B1 O1 9.8(6) . . . . ?
C402 C401 B1 C301 66.6(5) . . . . ?
C406 C401 B1 C301 -112.1(4) . . . . ?
C402 C401 B1 N1 -58.1(5) . . . . ?
C406 C401 B1 N1 123.2(4) . . . . ?
C302 C301 B1 O1 103.6(4) . . . . ?
C306 C301 B1 O1 -70.9(4) . . . . ?
C302 C301 B1 C401 -130.1(4) . . . . ?
C306 C301 B1 C401 55.4(5) . . . . ?
C302 C301 B1 N1 -5.6(6) . . . . ?
C306 C301 B1 N1 180.0(3) . . . . ?
C114 N1 B1 O1 -15.5(4) . . . . ?
C201 N1 B1 O1 114.7(4) . . . . ?
C114 N1 B1 C401 -137.3(3) . . . . ?
C201 N1 B1 C401 -7.1(5) . . . . ?
C114 N1 B1 C301 97.5(3) . . . . ?
C201 N1 B1 C301 -132.3(4) . . . . ?
C401 B1 O1 C101 136.9(3) . . . . ?
C301 B1 O1 C101 -98.4(3) . . . . ?
N1 B1 O1 C101 17.8(4) . . . . ?
F406 C406 C405 F405 0.1(6) . . . . ?
C401 C406 C405 F405 -179.7(4) . . . . ?
F406 C406 C405 C404 179.9(4) . . . . ?
C401 C406 C405 C404 0.1(6) . . . . ?
F306 C306 C305 F305 -0.8(6) . . . . ?
C301 C306 C305 F305 179.1(4) . . . . ?
F306 C306 C305 C304 178.9(4) . . . . ?
C301 C306 C305 C304 -1.2(6) . . . . ?
F304 C304 C305 F305 -1.1(6) . . . . ?
C303 C304 C305 F305 179.1(4) . . . . ?
F304 C304 C305 C306 179.2(4) . . . . ?
C303 C304 C305 C306 -0.6(6) . . . . ?
F403 C403 C404 F404 -1.9(6) . . . . ?
C402 C403 C404 F404 177.9(4) . . . . ?
F403 C403 C404 C405 179.2(4) . . . . ?
C402 C403 C404 C405 -1.0(6) . . . . ?
F405 C405 C404 F404 0.6(6) . . . . ?
C406 C405 C404 F404 -179.2(4) . . . . ?
F405 C405 C404 C403 179.5(4) . . . . ?
C406 C405 C404 C403 -0.3(6) . . . . ?
B1 O1 C101 C114 -14.7(5) . . . . ?
B1 O1 C101 C102 166.7(4) . . . . ?
C114 C101 C102 C103 179.6(4) . . . . ?
O1 C101 C102 C103 -1.8(6) . . . . ?
C114 C101 C102 C107 -0.3(6) . . . . ?
O1 C101 C102 C107 178.2(3) . . . . ?
C107 C102 C103 C104 1.1(6) . . . . ?
C101 C102 C103 C104 -178.8(4) . . . . ?
C102 C103 C104 C105 0.0(7) . . . . ?
C103 C104 C105 C106 -0.8(7) . . . . ?
C104 C105 C106 C107 0.6(7) . . . . ?
C105 C106 C107 C102 0.5(6) . . . . ?
C105 C106 C107 C108 -179.3(4) . . . . ?
C103 C102 C107 C106 -1.3(6) . . . . ?
C101 C102 C107 C106 178.6(4) . . . . ?
C103 C102 C107 C108 178.5(4) . . . . ?
C101 C102 C107 C108 -1.6(6) . . . . ?
C106 C107 C108 C109 2.5(6) . . . . ?
C102 C107 C108 C109 -177.3(4) . . . . ?
C106 C107 C108 C113 -178.5(4) . . . . ?
C102 C107 C108 C113 1.8(6) . . . . ?
C113 C108 C109 C110 0.9(6) . . . . ?
C107 C108 C109 C110 179.9(4) . . . . ?
C108 C109 C110 C111 -0.2(7) . . . . ?
C109 C110 C111 C112 -0.5(7) . . . . ?
C110 C111 C112 C113 0.5(7) . . . . ?
C111 C112 C113 C108 0.3(6) . . . . ?
C111 C112 C113 C114 -179.7(4) . . . . ?
C109 C108 C113 C112 -0.9(6) . . . . ?
C107 C108 C113 C112 -180.0(4) . . . . ?
C109 C108 C113 C114 179.0(4) . . . . ?
C107 C108 C113 C114 0.0(6) . . . . ?
O1 C101 C114 C113 -176.5(3) . . . . ?
C102 C101 C114 C113 2.2(6) . . . . ?
O1 C101 C114 N1 2.7(5) . . . . ?
C102 C101 C114 N1 -178.6(3) . . . . ?
C112 C113 C114 C101 178.0(4) . . . . ?
C108 C113 C114 C101 -1.9(6) . . . . ?
C112 C113 C114 N1 -1.0(6) . . . . ?
C108 C113 C114 N1 179.0(4) . . . . ?
C201 N1 C114 C101 -124.1(4) . . . . ?
B1 N1 C114 C101 8.5(4) . . . . ?
C201 N1 C114 C113 55.1(5) . . . . ?
B1 N1 C114 C113 -172.4(4) . . . . ?
C114 N1 C201 C206 58.8(5) . . . . ?
B1 N1 C201 C206 -63.9(5) . . . . ?
C114 N1 C201 C202 -121.0(4) . . . . ?
B1 N1 C201 C202 116.3(4) . . . . ?
C202 C201 C206 C205 -1.4(6) . . . . ?
N1 C201 C206 C205 178.9(3) . . . . ?
C202 C201 C206 C2 177.6(4) . . . . ?
N1 C201 C206 C2 -2.2(6) . . . . ?
C201 C206 C205 C204 0.2(6) . . . . ?
C2 C206 C205 C204 -178.8(4) . . . . ?
C206 C205 C204 C203 1.3(7) . . . . ?
C205 C204 C203 C202 -1.7(7) . . . . ?
C204 C203 C202 C201 0.5(6) . . . . ?
C204 C203 C202 C1 -180.0(4) . . . . ?
C206 C201 C202 C203 1.0(6) . . . . ?
N1 C201 C202 C203 -179.2(3) . . . . ?
C206 C201 C202 C1 -178.5(4) . . . . ?
N1 C201 C202 C1 1.3(5) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_compound_10
_database_code_depnum_ccdc_archive 'CCDC 1535317'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C49 H35 B1 F10 N2'
_chemical_formula_weight         852.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   50.971(13)
_cell_length_b                   17.609(4)
_cell_length_c                   18.424(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.812(15)
_cell_angle_gamma                90
_cell_volume                     15987(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7014
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.72

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             7008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63167
_diffrn_reflns_av_unetI/netI     0.1283
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         0.826
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             15404
_reflns_number_gt                7092
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0888P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15404
_refine_ls_number_parameters     1173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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
B01 B 1.41013(8) 0.5295(2) 1.6824(3) 0.0246(10) Uani 1 1 d . . . . .
B02 B 1.09020(8) 0.5162(2) 1.3193(3) 0.0263(10) Uani 1 1 d . . . . .
N01 N 1.34328(6) 0.42839(17) 1.67679(18) 0.0267(7) Uani 1 1 d D . . . .
H1N H 1.3595(5) 0.4189(19) 1.7080(18) 0.032 Uiso 1 1 d D U . . .
N02 N 1.38330(6) 0.53769(15) 1.68570(17) 0.0228(7) Uani 1 1 d . . . . .
N03 N 1.15767(6) 0.41682(17) 1.41612(19) 0.0280(8) Uani 1 1 d D . . . .
H3N H 1.1410(5) 0.406(2) 1.422(2) 0.046(12) Uiso 1 1 d D . . . .
N04 N 1.11684(6) 0.52474(15) 1.36237(17) 0.0233(7) Uani 1 1 d . . . . .
F002 F 1.04084(4) 0.43691(12) 1.31727(15) 0.0442(6) Uani 1 1 d . . . . .
F003 F 0.99658(5) 0.49738(15) 1.34477(18) 0.0643(8) Uani 1 1 d . . . . .
F004 F 0.99663(5) 0.64422(17) 1.3863(2) 0.0825(10) Uani 1 1 d . . . . .
F005 F 1.04170(6) 0.73068(14) 1.39765(18) 0.0722(9) Uani 1 1 d . . . . .
F006 F 1.08550(5) 0.67155(12) 1.36916(14) 0.0445(6) Uani 1 1 d . . . . .
F402 F 1.39328(4) 0.37595(11) 1.63224(13) 0.0397(6) Uani 1 1 d . . . . .
F403 F 1.40845(5) 0.30183(15) 1.52489(17) 0.0675(9) Uani 1 1 d . . . . .
F404 F 1.44111(6) 0.36839(18) 1.45000(17) 0.0763(9) Uani 1 1 d . . . . .
F405 F 1.45881(5) 0.51145(16) 1.48399(15) 0.0578(7) Uani 1 1 d . . . . .
F406 F 1.44363(4) 0.58751(12) 1.59154(13) 0.0402(6) Uani 1 1 d . . . . .
F502 F 1.45944(4) 0.45118(12) 1.75471(14) 0.0438(6) Uani 1 1 d . . . . .
F503 F 1.50320(5) 0.51332(15) 1.84637(16) 0.0604(8) Uani 1 1 d . . . . .
F504 F 1.50268(5) 0.66053(17) 1.88459(19) 0.0797(10) Uani 1 1 d . . . . .
F505 F 1.45749(6) 0.74578(14) 1.82986(19) 0.0745(9) Uani 1 1 d . . . . .
F506 F 1.41384(4) 0.68457(11) 1.73898(14) 0.0429(6) Uani 1 1 d . . . . .
F902 F 1.10717(4) 0.36254(12) 1.29462(14) 0.0421(6) Uani 1 1 d . . . . .
F903 F 1.09224(6) 0.28741(15) 1.16526(17) 0.0698(9) Uani 1 1 d . . . . .
F904 F 1.06055(6) 0.35453(17) 1.04234(16) 0.0731(9) Uani 1 1 d . . . . .
F905 F 1.04310(5) 0.49795(16) 1.04988(14) 0.0569(7) Uani 1 1 d . . . . .
F906 F 1.05765(4) 0.57470(12) 1.17895(13) 0.0420(6) Uani 1 1 d . . . . .
C1 C 1.28926(9) 0.7434(3) 1.4829(3) 0.0770(18) Uani 1 1 d . . . . .
H1A H 1.3042 0.7459 1.4585 0.116 Uiso 1 1 calc R U . . .
H1B H 1.2926 0.7019 1.5196 0.116 Uiso 1 1 calc R U . . .
H1C H 1.2881 0.7915 1.5085 0.116 Uiso 1 1 calc R U . . .
C2 C 1.26329(8) 0.7293(3) 1.4253(3) 0.0426(12) Uani 1 1 d . . . . .
C3 C 1.25204(10) 0.6579(2) 1.4130(3) 0.0463(12) Uani 1 1 d . . . . .
H3 H 1.2605 0.6166 1.4433 0.056 Uiso 1 1 calc R U . . .
C4 C 1.22862(11) 0.6456(3) 1.3571(3) 0.0547(14) Uani 1 1 d . . . . .
H4 H 1.2212 0.5959 1.3492 0.066 Uiso 1 1 calc R U . . .
C5 C 1.21606(9) 0.7040(3) 1.3133(3) 0.0566(14) Uani 1 1 d . . . . .
H5 H 1.2000 0.6951 1.2747 0.068 Uiso 1 1 calc R U . . .
C6 C 1.22665(10) 0.7747(3) 1.3253(3) 0.0559(13) Uani 1 1 d . . . . .
H6 H 1.2178 0.8158 1.2953 0.067 Uiso 1 1 calc R U . . .
C7 C 1.24992(10) 0.7874(3) 1.3802(3) 0.0495(13) Uani 1 1 d . . . . .
H7 H 1.2571 0.8374 1.3875 0.059 Uiso 1 1 calc R U . . .
C9A C 0.97093(17) 1.2334(4) 1.1447(5) 0.066(3) Uani 0.5 1 d G . P A -1
C10A C 0.9722(3) 1.2931(4) 1.0962(6) 0.171(10) Uani 0.5 1 d G . P A -1
H10A H 0.9613 1.3369 1.0955 0.206 Uiso 0.5 1 calc R U P A -1
C11A C 0.9894(3) 1.2886(5) 1.0489(6) 0.187(15) Uani 0.5 1 d G . P A -1
H11A H 0.9903 1.3294 1.0158 0.225 Uiso 0.5 1 calc R U P A -1
C12A C 1.0054(2) 1.2245(6) 1.0499(5) 0.113(8) Uani 0.5 1 d G . P A -1
H12A H 1.0172 1.2214 1.0176 0.135 Uiso 0.5 1 calc R U P A -1
C13A C 1.00417(16) 1.1648(5) 1.0983(5) 0.084(4) Uani 0.5 1 d G . P A -1
H13A H 1.0151 1.1210 1.0991 0.100 Uiso 0.5 1 calc R U P A -1
C14A C 0.98693(16) 1.1693(4) 1.1457(4) 0.061(3) Uani 0.5 1 d G . P A -1
H14A H 0.9861 1.1285 1.1788 0.073 Uiso 0.5 1 calc R U P A -1
C8B C 0.9520(10) 1.248(3) 1.202(4) 0.135(19) Uani 0.5 1 d . . P A -1
H8BA H 0.9524 1.2029 1.2339 0.203 Uiso 0.5 1 calc R U P A -1
H8BB H 0.9588 1.2919 1.2342 0.203 Uiso 0.5 1 calc R U P A -1
H8BC H 0.9333 1.2577 1.1737 0.203 Uiso 0.5 1 calc R U P A -1
C9B C 1.00247(17) 1.3207(4) 1.4073(5) 0.088(4) Uani 0.5 1 d G . P B -2
H9BA H 1.0131 1.3649 1.4229 0.105 Uiso 0.5 1 calc R U P B -2
C10B C 0.98630(17) 1.3152(4) 1.3343(5) 0.075(3) Uani 0.5 1 d G . P B -2
H10B H 0.9859 1.3557 1.2999 0.090 Uiso 0.5 1 calc R U P B -2
C13B C 0.97076(18) 1.2505(5) 1.3115(5) 0.080(4) Uani 0.5 1 d G . P B -2
C14B C 0.9714(3) 1.1913(4) 1.3618(6) 0.171(10) Uani 0.5 1 d G . P B -2
H14B H 0.9607 1.1471 1.3462 0.205 Uiso 0.5 1 calc R U P B -2
C11B C 0.9875(3) 1.1968(5) 1.4348(5) 0.159(12) Uani 0.5 1 d G . P B -2
H11B H 0.9880 1.1563 1.4692 0.190 Uiso 0.5 1 calc R U P B -2
C12B C 1.0031(2) 1.2615(5) 1.4576(4) 0.096(6) Uani 0.5 1 d G . P B -2
H12B H 1.0141 1.2652 1.5075 0.116 Uiso 0.5 1 calc R U P B -2
C8A C 0.9567(9) 1.239(3) 1.224(3) 0.096(10) Uani 0.5 1 d . . P B -2
H8AA H 0.9464 1.1917 1.2163 0.144 Uiso 0.5 1 calc R U P B -2
H8AB H 0.9443 1.2819 1.2058 0.144 Uiso 0.5 1 calc R U P B -2
H8AC H 0.9706 1.2379 1.1960 0.144 Uiso 0.5 1 calc R U P B -2
C01 C 1.35160(8) 0.2814(2) 1.7359(2) 0.0368(10) Uani 1 1 d . . . . .
H01A H 1.3672 0.3044 1.7717 0.055 Uiso 1 1 calc R U . . .
H01B H 1.3547 0.2823 1.6855 0.055 Uiso 1 1 calc R U . . .
H01C H 1.3495 0.2287 1.7506 0.055 Uiso 1 1 calc R U . . .
C02 C 1.29527(8) 0.5211(2) 1.6840(3) 0.0387(11) Uani 1 1 d . . . . .
H02A H 1.2884 0.5233 1.6293 0.058 Uiso 1 1 calc R U . . .
H02B H 1.3126 0.5482 1.6992 0.058 Uiso 1 1 calc R U . . .
H02C H 1.2821 0.5449 1.7076 0.058 Uiso 1 1 calc R U . . .
C03 C 1.40305(8) 0.4434(2) 1.8218(2) 0.0325(10) Uani 1 1 d . . . . .
H03A H 1.3968 0.4029 1.8498 0.049 Uiso 1 1 calc R U . . .
H03B H 1.4218 0.4571 1.8473 0.049 Uiso 1 1 calc R U . . .
H03C H 1.4023 0.4256 1.7709 0.049 Uiso 1 1 calc R U . . .
C04 C 1.34957(8) 0.6735(2) 1.6913(2) 0.0327(10) Uani 1 1 d . . . . .
H04A H 1.3432 0.7206 1.7092 0.049 Uiso 1 1 calc R U . . .
H04B H 1.3347 0.6499 1.6537 0.049 Uiso 1 1 calc R U . . .
H04C H 1.3646 0.6848 1.6688 0.049 Uiso 1 1 calc R U . . .
C05 C 1.15098(9) 0.2692(2) 1.4661(3) 0.0412(11) Uani 1 1 d . . . . .
H05A H 1.1354 0.2893 1.4818 0.062 Uiso 1 1 calc R U . . .
H05B H 1.1540 0.2161 1.4822 0.062 Uiso 1 1 calc R U . . .
H05C H 1.1474 0.2720 1.4113 0.062 Uiso 1 1 calc R U . . .
C06 C 1.20499(8) 0.5132(2) 1.4898(3) 0.0415(11) Uani 1 1 d . . . . .
H06A H 1.2191 0.5371 1.5295 0.062 Uiso 1 1 calc R U . . .
H06B H 1.1878 0.5404 1.4844 0.062 Uiso 1 1 calc R U . . .
H06C H 1.2103 0.5153 1.4423 0.062 Uiso 1 1 calc R U . . .
C07 C 1.09665(8) 0.4312(2) 1.4689(2) 0.0340(10) Uani 1 1 d . . . . .
H07A H 1.0777 0.4432 1.4663 0.051 Uiso 1 1 calc R U . . .
H07B H 1.1030 0.3913 1.5064 0.051 Uiso 1 1 calc R U . . .
H07C H 1.0982 0.4135 1.4198 0.051 Uiso 1 1 calc R U . . .
C08 C 1.14927(8) 0.6631(2) 1.4159(2) 0.0335(10) Uani 1 1 d . . . . .
H08A H 1.1642 0.6394 1.3999 0.050 Uiso 1 1 calc R U . . .
H08B H 1.1556 0.7102 1.4430 0.050 Uiso 1 1 calc R U . . .
H08C H 1.1344 0.6745 1.3718 0.050 Uiso 1 1 calc R U . . .
C001 C 1.06409(8) 0.6251(2) 1.3640(2) 0.0339(10) Uani 1 1 d . . . . .
C002 C 1.04170(7) 0.5102(2) 1.3375(2) 0.0327(10) Uani 1 1 d . . . . .
C003 C 1.01882(8) 0.5400(2) 1.3511(3) 0.0421(11) Uani 1 1 d . . . . .
C004 C 1.01872(8) 0.6145(3) 1.3717(3) 0.0498(13) Uani 1 1 d . . . . .
C005 C 1.04120(9) 0.6575(2) 1.3774(3) 0.0454(12) Uani 1 1 d . . . . .
C006 C 1.06532(7) 0.5507(2) 1.3436(2) 0.0289(9) Uani 1 1 d . . . . .
C101 C 1.36164(7) 0.52824(19) 1.6186(2) 0.0234(8) Uani 1 1 d . . . . .
C102 C 1.36168(7) 0.5759(2) 1.5555(2) 0.0264(9) Uani 1 1 d . . . . .
C103 C 1.38170(7) 0.6315(2) 1.5578(2) 0.0278(9) Uani 1 1 d . . . . .
H103 H 1.3960 0.6371 1.6020 0.033 Uiso 1 1 calc R U . . .
C104 C 1.38097(8) 0.6772(2) 1.4982(2) 0.0328(10) Uani 1 1 d . . . . .
H104 H 1.3947 0.7143 1.5009 0.039 Uiso 1 1 calc R U . . .
C105 C 1.36026(8) 0.6702(2) 1.4333(2) 0.0330(10) Uani 1 1 d . . . . .
H105 H 1.3598 0.7025 1.3917 0.040 Uiso 1 1 calc R U . . .
C106 C 1.34050(8) 0.6169(2) 1.4291(2) 0.0326(10) Uani 1 1 d . . . . .
H106 H 1.3265 0.6120 1.3841 0.039 Uiso 1 1 calc R U . . .
C107 C 1.34050(7) 0.56914(19) 1.4899(2) 0.0259(9) Uani 1 1 d . . . . .
C108 C 1.31955(7) 0.5128(2) 1.4856(2) 0.0254(9) Uani 1 1 d . . . . .
C109 C 1.29867(8) 0.5022(2) 1.4205(3) 0.0419(11) Uani 1 1 d . . . . .
H109 H 1.2978 0.5344 1.3785 0.050 Uiso 1 1 calc R U . . .
C110 C 1.27960(8) 0.4471(2) 1.4156(3) 0.0446(12) Uani 1 1 d . . . . .
H110 H 1.2652 0.4426 1.3714 0.054 Uiso 1 1 calc R U . . .
C111 C 1.28114(8) 0.3976(2) 1.4748(3) 0.0387(11) Uani 1 1 d . . . . .
H111 H 1.2681 0.3582 1.4708 0.046 Uiso 1 1 calc R U . . .
C112 C 1.30145(7) 0.4055(2) 1.5392(2) 0.0313(9) Uani 1 1 d . . . . .
H112 H 1.3027 0.3705 1.5791 0.038 Uiso 1 1 calc R U . . .
C113 C 1.32063(7) 0.4651(2) 1.5473(2) 0.0266(9) Uani 1 1 d . . . . .
C114 C 1.34163(7) 0.47552(19) 1.6156(2) 0.0235(8) Uani 1 1 d . . . . .
C201 C 1.32241(7) 0.3987(2) 1.7064(2) 0.0256(9) Uani 1 1 d . . . . .
C202 C 1.32642(8) 0.3253(2) 1.7357(2) 0.0279(9) Uani 1 1 d . . . . .
C203 C 1.30636(8) 0.2931(2) 1.7639(2) 0.0356(10) Uani 1 1 d . . . . .
H203 H 1.3089 0.2435 1.7848 0.043 Uiso 1 1 calc R U . . .
C204 C 1.28278(8) 0.3319(2) 1.7624(2) 0.0380(11) Uani 1 1 d . . . . .
H204 H 1.2688 0.3083 1.7801 0.046 Uiso 1 1 calc R U . . .
C205 C 1.27954(7) 0.4045(2) 1.7354(2) 0.0319(10) Uani 1 1 d . . . . .
H205 H 1.2633 0.4311 1.7351 0.038 Uiso 1 1 calc R U . . .
C206 C 1.29934(7) 0.4399(2) 1.7085(2) 0.0278(9) Uani 1 1 d . . . . .
C301 C 1.37600(7) 0.5574(2) 1.7545(2) 0.0252(9) Uani 1 1 d . . . . .
C302 C 1.38501(7) 0.5120(2) 1.8176(2) 0.0271(9) Uani 1 1 d . . . . .
C303 C 1.37679(8) 0.5292(2) 1.8813(2) 0.0331(10) Uani 1 1 d . . . . .
H303 H 1.3828 0.4982 1.9246 0.040 Uiso 1 1 calc R U . . .
C304 C 1.36017(8) 0.5898(2) 1.8839(3) 0.0381(11) Uani 1 1 d . . . . .
H304 H 1.3547 0.6008 1.9284 0.046 Uiso 1 1 calc R U . . .
C305 C 1.35168(8) 0.6342(2) 1.8217(2) 0.0352(10) Uani 1 1 d . . . . .
H305 H 1.3402 0.6763 1.8237 0.042 Uiso 1 1 calc R U . . .
C306 C 1.35913(7) 0.6203(2) 1.7558(2) 0.0278(9) Uani 1 1 d . . . . .
C401 C 1.41743(7) 0.4857(2) 1.6160(2) 0.0263(9) Uani 1 1 d . . . . .
C402 C 1.40929(7) 0.4128(2) 1.5956(2) 0.0324(10) Uani 1 1 d . . . . .
C403 C 1.41710(8) 0.3726(2) 1.5419(3) 0.0413(11) Uani 1 1 d . . . . .
C404 C 1.43381(9) 0.4062(3) 1.5040(3) 0.0465(12) Uani 1 1 d . . . . .
C405 C 1.44257(8) 0.4784(3) 1.5216(2) 0.0411(11) Uani 1 1 d . . . . .
C406 C 1.43457(7) 0.5164(2) 1.5764(2) 0.0317(10) Uani 1 1 d . . . . .
C501 C 1.43469(7) 0.5644(2) 1.7438(2) 0.0271(9) Uani 1 1 d . . . . .
C502 C 1.45817(7) 0.5248(2) 1.7725(2) 0.0305(9) Uani 1 1 d . . . . .
C503 C 1.48092(8) 0.5552(2) 1.8197(2) 0.0388(11) Uani 1 1 d . . . . .
C504 C 1.48077(8) 0.6301(3) 1.8388(3) 0.0486(12) Uani 1 1 d . . . . .
C505 C 1.45792(9) 0.6723(2) 1.8109(3) 0.0458(12) Uani 1 1 d . . . . .
C506 C 1.43559(8) 0.6391(2) 1.7654(2) 0.0333(10) Uani 1 1 d . . . . .
C601 C 1.13916(7) 0.51449(19) 1.3277(2) 0.0233(8) Uani 1 1 d . . . . .
C602 C 1.13982(7) 0.5621(2) 1.2656(2) 0.0264(9) Uani 1 1 d . . . . .
C603 C 1.12006(8) 0.6185(2) 1.2380(2) 0.0311(9) Uani 1 1 d . . . . .
H603 H 1.1051 0.6232 1.2596 0.037 Uiso 1 1 calc R U . . .
C604 C 1.12176(9) 0.6664(2) 1.1813(2) 0.0376(10) Uani 1 1 d . . . . .
H604 H 1.1083 0.7041 1.1640 0.045 Uiso 1 1 calc R U . . .
C605 C 1.14344(9) 0.6593(2) 1.1491(2) 0.0391(11) Uani 1 1 d . . . . .
H605 H 1.1449 0.6925 1.1097 0.047 Uiso 1 1 calc R U . . .
C606 C 1.16267(8) 0.6051(2) 1.1735(2) 0.0342(10) Uani 1 1 d . . . . .
H606 H 1.1773 0.6013 1.1506 0.041 Uiso 1 1 calc R U . . .
C607 C 1.16146(7) 0.5548(2) 1.2315(2) 0.0283(9) Uani 1 1 d . . . . .
C608 C 1.18153(7) 0.4961(2) 1.2569(2) 0.0289(9) Uani 1 1 d . . . . .
C609 C 1.20202(8) 0.4818(2) 1.2204(3) 0.0388(11) Uani 1 1 d . . . . .
H609 H 1.2035 0.5134 1.1798 0.047 Uiso 1 1 calc R U . . .
C610 C 1.21977(8) 0.4240(3) 1.2417(3) 0.0423(12) Uani 1 1 d . . . . .
H610 H 1.2337 0.4164 1.2167 0.051 Uiso 1 1 calc R U . . .
C611 C 1.21795(8) 0.3757(2) 1.2994(2) 0.0370(11) Uani 1 1 d . . . . .
H611 H 1.2303 0.3346 1.3133 0.044 Uiso 1 1 calc R U . . .
C612 C 1.19821(7) 0.3877(2) 1.3360(2) 0.0331(10) Uani 1 1 d . . . . .
H612 H 1.1967 0.3538 1.3749 0.040 Uiso 1 1 calc R U . . .
C613 C 1.18000(7) 0.4495(2) 1.3173(2) 0.0266(9) Uani 1 1 d . . . . .
C614 C 1.15899(7) 0.46246(19) 1.3561(2) 0.0231(8) Uani 1 1 d . . . . .
C701 C 1.17865(7) 0.3890(2) 1.4758(2) 0.0267(9) Uani 1 1 d . . . . .
C702 C 1.20156(7) 0.4325(2) 1.5099(2) 0.0296(9) Uani 1 1 d . . . . .
C703 C 1.22172(8) 0.3991(2) 1.5664(2) 0.0367(10) Uani 1 1 d . . . . .
H703 H 1.2377 0.4271 1.5883 0.044 Uiso 1 1 calc R U . . .
C704 C 1.21909(9) 0.3268(2) 1.5911(3) 0.0427(11) Uani 1 1 d . . . . .
H704 H 1.2330 0.3051 1.6299 0.051 Uiso 1 1 calc R U . . .
C705 C 1.19599(8) 0.2859(2) 1.5591(2) 0.0378(11) Uani 1 1 d . . . . .
H705 H 1.1940 0.2362 1.5771 0.045 Uiso 1 1 calc R U . . .
C706 C 1.17574(8) 0.3152(2) 1.5014(2) 0.0295(9) Uani 1 1 d . . . . .
C801 C 1.12345(7) 0.54621(19) 1.4404(2) 0.0235(8) Uani 1 1 d . . . . .
C802 C 1.11377(7) 0.50124(19) 1.4910(2) 0.0260(9) Uani 1 1 d . . . . .
C803 C 1.12079(7) 0.5212(2) 1.5654(2) 0.0320(10) Uani 1 1 d . . . . .
H803 H 1.1144 0.4911 1.6001 0.038 Uiso 1 1 calc R U . . .
C804 C 1.13675(8) 0.5832(2) 1.5917(2) 0.0343(10) Uani 1 1 d . . . . .
H804 H 1.1414 0.5955 1.6436 0.041 Uiso 1 1 calc R U . . .
C805 C 1.14592(8) 0.6271(2) 1.5419(2) 0.0322(10) Uani 1 1 d . . . . .
H805 H 1.1570 0.6701 1.5597 0.039 Uiso 1 1 calc R U . . .
C806 C 1.13943(7) 0.61012(19) 1.4662(2) 0.0276(9) Uani 1 1 d . . . . .
C901 C 1.08327(7) 0.4726(2) 1.2418(2) 0.0275(9) Uani 1 1 d . . . . .
C902 C 1.09136(8) 0.3985(2) 1.2347(2) 0.0337(10) Uani 1 1 d . . . . .
C903 C 1.08368(8) 0.3588(2) 1.1691(3) 0.0422(11) Uani 1 1 d . . . . .
C904 C 1.06751(9) 0.3919(3) 1.1072(3) 0.0488(12) Uani 1 1 d . . . . .
C905 C 1.05869(8) 0.4646(3) 1.1109(2) 0.0405(11) Uani 1 1 d . . . . .
C906 C 1.06654(7) 0.5029(2) 1.1781(2) 0.0335(10) 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
B01 N02 1.391(5) . ?
B01 C401 1.570(6) . ?
B01 C501 1.581(6) . ?
B02 N04 1.395(5) . ?
B02 C006 1.571(5) . ?
B02 C901 1.579(6) . ?
N01 C114 1.386(5) . ?
N01 C201 1.415(4) . ?
N02 C101 1.441(5) . ?
N02 C301 1.451(5) . ?
N03 C614 1.383(5) . ?
N03 C701 1.411(5) . ?
N04 C801 1.440(5) . ?
N04 C601 1.451(4) . ?
F002 C002 1.341(4) . ?
F003 C003 1.340(5) . ?
F004 C004 1.330(4) . ?
F005 C005 1.340(4) . ?
F006 C001 1.348(4) . ?
F402 C402 1.351(4) . ?
F403 C403 1.332(5) . ?
F404 C404 1.327(5) . ?
F405 C405 1.341(5) . ?
F406 C406 1.340(4) . ?
F502 C502 1.343(4) . ?
F503 C503 1.338(5) . ?
F504 C504 1.329(5) . ?
F505 C505 1.341(4) . ?
F506 C506 1.353(4) . ?
F902 C902 1.348(5) . ?
F903 C903 1.338(5) . ?
F904 C904 1.330(5) . ?
F905 C905 1.336(5) . ?
F906 C906 1.345(4) . ?
C1 C2 1.491(6) . ?
C2 C3 1.377(6) . ?
C2 C7 1.383(6) . ?
C3 C4 1.379(7) . ?
C4 C5 1.362(7) . ?
C5 C6 1.353(7) . ?
C6 C7 1.366(7) . ?
C9A C10A 1.3900 . ?
C9A C14A 1.3900 . ?
C9A C8B 1.63(6) . ?
C10A C11A 1.3900 . ?
C11A C12A 1.3900 . ?
C12A C13A 1.3900 . ?
C13A C14A 1.3900 . ?
C9B C10B 1.3900 . ?
C9B C12B 1.3900 . ?
C10B C13B 1.3900 . ?
C13B C14B 1.3900 . ?
C13B C8A 1.60(5) . ?
C14B C11B 1.3900 . ?
C11B C12B 1.3900 . ?
C01 C202 1.498(5) . ?
C02 C206 1.497(5) . ?
C03 C302 1.507(5) . ?
C04 C306 1.493(5) . ?
C05 C706 1.501(5) . ?
C06 C702 1.490(5) . ?
C07 C802 1.506(5) . ?
C08 C806 1.489(5) . ?
C001 C006 1.369(5) . ?
C001 C005 1.376(5) . ?
C002 C003 1.359(5) . ?
C002 C006 1.379(5) . ?
C003 C004 1.365(6) . ?
C004 C005 1.355(6) . ?
C101 C114 1.370(5) . ?
C101 C102 1.434(5) . ?
C102 C107 1.405(5) . ?
C102 C103 1.407(5) . ?
C103 C104 1.355(5) . ?
C104 C105 1.383(6) . ?
C105 C106 1.364(5) . ?
C106 C107 1.401(5) . ?
C107 C108 1.446(5) . ?
C108 C109 1.397(6) . ?
C108 C113 1.403(5) . ?
C109 C110 1.361(6) . ?
C110 C111 1.382(6) . ?
C111 C112 1.367(6) . ?
C112 C113 1.415(5) . ?
C113 C114 1.440(5) . ?
C201 C206 1.391(5) . ?
C201 C202 1.395(5) . ?
C202 C203 1.381(5) . ?
C203 C204 1.376(6) . ?
C204 C205 1.366(5) . ?
C205 C206 1.382(5) . ?
C301 C302 1.389(5) . ?
C301 C306 1.406(5) . ?
C302 C303 1.378(5) . ?
C303 C304 1.372(5) . ?
C304 C305 1.363(6) . ?
C305 C306 1.385(5) . ?
C401 C402 1.371(5) . ?
C401 C406 1.383(5) . ?
C402 C403 1.356(5) . ?
C403 C404 1.368(6) . ?
C404 C405 1.359(6) . ?
C405 C406 1.358(6) . ?
C501 C502 1.369(5) . ?
C501 C506 1.373(5) . ?
C502 C503 1.368(5) . ?
C503 C504 1.365(6) . ?
C504 C505 1.367(6) . ?
C505 C506 1.361(6) . ?
C601 C614 1.365(5) . ?
C601 C602 1.426(5) . ?
C602 C607 1.408(5) . ?
C602 C603 1.414(5) . ?
C603 C604 1.362(5) . ?
C604 C605 1.386(6) . ?
C605 C606 1.359(6) . ?
C606 C607 1.401(5) . ?
C607 C608 1.445(5) . ?
C608 C613 1.401(5) . ?
C608 C609 1.402(5) . ?
C609 C610 1.352(6) . ?
C610 C611 1.382(6) . ?
C611 C612 1.364(5) . ?
C612 C613 1.415(5) . ?
C613 C614 1.450(5) . ?
C701 C706 1.402(5) . ?
C701 C702 1.404(5) . ?
C702 C703 1.392(5) . ?
C703 C704 1.371(6) . ?
C704 C705 1.378(6) . ?
C705 C706 1.379(6) . ?
C801 C806 1.400(5) . ?
C801 C802 1.405(5) . ?
C802 C803 1.372(6) . ?
C803 C804 1.374(5) . ?
C804 C805 1.370(5) . ?
C805 C806 1.380(5) . ?
C901 C906 1.369(5) . ?
C901 C902 1.385(5) . ?
C902 C903 1.364(6) . ?
C903 C904 1.357(6) . ?
C904 C905 1.365(6) . ?
C905 C906 1.376(6) . ?

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
N02 B01 C401 121.1(3) . . ?
N02 B01 C501 122.4(3) . . ?
C401 B01 C501 116.5(3) . . ?
N04 B02 C006 122.4(4) . . ?
N04 B02 C901 121.8(3) . . ?
C006 B02 C901 115.8(3) . . ?
C114 N01 C201 129.8(3) . . ?
B01 N02 C101 119.8(3) . . ?
B01 N02 C301 122.5(3) . . ?
C101 N02 C301 117.7(3) . . ?
C614 N03 C701 130.1(3) . . ?
B02 N04 C801 122.8(3) . . ?
B02 N04 C601 119.7(3) . . ?
C801 N04 C601 117.5(3) . . ?
C3 C2 C7 117.2(4) . . ?
C3 C2 C1 121.7(5) . . ?
C7 C2 C1 121.1(4) . . ?
C2 C3 C4 120.7(5) . . ?
C5 C4 C3 120.7(4) . . ?
C6 C5 C4 119.4(5) . . ?
C5 C6 C7 120.4(5) . . ?
C6 C7 C2 121.7(4) . . ?
C10A C9A C14A 120.0 . . ?
C10A C9A C8B 115.6(19) . . ?
C14A C9A C8B 124(2) . . ?
C9A C10A C11A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C13A C14A C9A 120.0 . . ?
C10B C9B C12B 120.0 . . ?
C9B C10B C13B 120.0 . . ?
C10B C13B C14B 120.0 . . ?
C10B C13B C8A 118.6(17) . . ?
C14B C13B C8A 120.5(18) . . ?
C13B C14B C11B 120.0 . . ?
C12B C11B C14B 120.0 . . ?
C11B C12B C9B 120.0 . . ?
F006 C001 C006 120.4(3) . . ?
F006 C001 C005 116.4(3) . . ?
C006 C001 C005 123.1(4) . . ?
F002 C002 C003 117.0(3) . . ?
F002 C002 C006 119.1(3) . . ?
C003 C002 C006 123.9(4) . . ?
F003 C003 C002 120.9(4) . . ?
F003 C003 C004 119.9(4) . . ?
C002 C003 C004 119.1(4) . . ?
F004 C004 C005 120.4(4) . . ?
F004 C004 C003 119.9(4) . . ?
C005 C004 C003 119.7(4) . . ?
F005 C005 C004 121.0(4) . . ?
F005 C005 C001 119.5(4) . . ?
C004 C005 C001 119.5(4) . . ?
C001 C006 C002 114.7(3) . . ?
C001 C006 B02 123.1(3) . . ?
C002 C006 B02 121.9(3) . . ?
C114 C101 C102 121.3(3) . . ?
C114 C101 N02 120.8(3) . . ?
C102 C101 N02 117.9(3) . . ?
C107 C102 C103 118.5(4) . . ?
C107 C102 C101 119.2(3) . . ?
C103 C102 C101 122.3(4) . . ?
C104 C103 C102 121.3(4) . . ?
C103 C104 C105 120.3(4) . . ?
C106 C105 C104 120.0(4) . . ?
C105 C106 C107 121.2(4) . . ?
C106 C107 C102 118.7(3) . . ?
C106 C107 C108 121.2(4) . . ?
C102 C107 C108 120.1(3) . . ?
C109 C108 C113 118.7(4) . . ?
C109 C108 C107 121.9(4) . . ?
C113 C108 C107 119.4(3) . . ?
C110 C109 C108 121.7(4) . . ?
C109 C110 C111 120.1(4) . . ?
C112 C111 C110 119.9(4) . . ?
C111 C112 C113 121.1(4) . . ?
C108 C113 C112 118.3(4) . . ?
C108 C113 C114 119.9(3) . . ?
C112 C113 C114 121.8(4) . . ?
C101 C114 N01 118.9(3) . . ?
C101 C114 C113 120.1(3) . . ?
N01 C114 C113 120.8(3) . . ?
C206 C201 C202 121.0(3) . . ?
C206 C201 N01 122.8(3) . . ?
C202 C201 N01 116.2(3) . . ?
C203 C202 C201 118.4(4) . . ?
C203 C202 C01 120.2(4) . . ?
C201 C202 C01 121.3(3) . . ?
C204 C203 C202 121.0(4) . . ?
C205 C204 C203 119.7(4) . . ?
C204 C205 C206 121.5(4) . . ?
C205 C206 C201 118.2(3) . . ?
C205 C206 C02 118.8(3) . . ?
C201 C206 C02 122.9(3) . . ?
C302 C301 C306 120.8(4) . . ?
C302 C301 N02 119.3(3) . . ?
C306 C301 N02 119.9(3) . . ?
C303 C302 C301 118.7(4) . . ?
C303 C302 C03 116.6(4) . . ?
C301 C302 C03 124.8(4) . . ?
C304 C303 C302 121.7(4) . . ?
C305 C304 C303 118.9(4) . . ?
C304 C305 C306 122.4(4) . . ?
C305 C306 C301 117.5(4) . . ?
C305 C306 C04 118.7(3) . . ?
C301 C306 C04 123.8(3) . . ?
C402 C401 C406 114.1(3) . . ?
C402 C401 B01 124.0(3) . . ?
C406 C401 B01 121.8(3) . . ?
F402 C402 C403 116.1(3) . . ?
F402 C402 C401 119.4(3) . . ?
C403 C402 C401 124.4(4) . . ?
F403 C403 C402 121.3(4) . . ?
F403 C403 C404 119.8(4) . . ?
C402 C403 C404 118.9(4) . . ?
F404 C404 C405 120.7(4) . . ?
F404 C404 C403 119.7(4) . . ?
C405 C404 C403 119.6(4) . . ?
F405 C405 C406 120.9(4) . . ?
F405 C405 C404 119.4(4) . . ?
C406 C405 C404 119.7(4) . . ?
F406 C406 C405 117.5(4) . . ?
F406 C406 C401 119.1(3) . . ?
C405 C406 C401 123.4(4) . . ?
C502 C501 C506 114.5(3) . . ?
C502 C501 B01 122.2(3) . . ?
C506 C501 B01 122.8(3) . . ?
F502 C502 C503 116.5(4) . . ?
F502 C502 C501 119.3(3) . . ?
C503 C502 C501 124.2(4) . . ?
F503 C503 C504 119.9(4) . . ?
F503 C503 C502 121.3(4) . . ?
C504 C503 C502 118.8(4) . . ?
F504 C504 C503 119.6(4) . . ?
F504 C504 C505 121.0(4) . . ?
C503 C504 C505 119.3(4) . . ?
F505 C505 C506 120.5(4) . . ?
F505 C505 C504 119.8(4) . . ?
C506 C505 C504 119.7(4) . . ?
F506 C506 C505 116.5(4) . . ?
F506 C506 C501 120.0(3) . . ?
C505 C506 C501 123.5(4) . . ?
C614 C601 C602 122.3(3) . . ?
C614 C601 N04 120.2(3) . . ?
C602 C601 N04 117.5(3) . . ?
C607 C602 C603 118.0(3) . . ?
C607 C602 C601 119.2(3) . . ?
C603 C602 C601 122.8(3) . . ?
C604 C603 C602 122.1(4) . . ?
C603 C604 C605 119.1(4) . . ?
C606 C605 C604 120.6(4) . . ?
C605 C606 C607 121.8(4) . . ?
C606 C607 C602 118.4(4) . . ?
C606 C607 C608 122.2(3) . . ?
C602 C607 C608 119.4(3) . . ?
C613 C608 C609 118.4(4) . . ?
C613 C608 C607 119.9(3) . . ?
C609 C608 C607 121.7(4) . . ?
C610 C609 C608 121.4(4) . . ?
C609 C610 C611 121.0(4) . . ?
C612 C611 C610 119.3(4) . . ?
C611 C612 C613 121.2(4) . . ?
C608 C613 C612 118.6(3) . . ?
C608 C613 C614 119.8(3) . . ?
C612 C613 C614 121.5(4) . . ?
C601 C614 N03 120.9(3) . . ?
C601 C614 C613 119.0(3) . . ?
N03 C614 C613 119.7(3) . . ?
C706 C701 C702 120.2(4) . . ?
C706 C701 N03 117.3(3) . . ?
C702 C701 N03 122.5(3) . . ?
C703 C702 C701 118.3(4) . . ?
C703 C702 C06 118.5(4) . . ?
C701 C702 C06 123.1(4) . . ?
C704 C703 C702 121.6(4) . . ?
C703 C704 C705 119.3(4) . . ?
C704 C705 C706 121.5(4) . . ?
C705 C706 C701 118.9(4) . . ?
C705 C706 C05 120.8(4) . . ?
C701 C706 C05 120.3(4) . . ?
C806 C801 C802 120.0(4) . . ?
C806 C801 N04 121.2(3) . . ?
C802 C801 N04 118.8(3) . . ?
C803 C802 C801 118.2(3) . . ?
C803 C802 C07 117.7(3) . . ?
C801 C802 C07 124.1(4) . . ?
C802 C803 C804 122.4(4) . . ?
C805 C804 C803 119.0(4) . . ?
C804 C805 C806 121.3(4) . . ?
C805 C806 C801 119.1(3) . . ?
C805 C806 C08 117.4(3) . . ?
C801 C806 C08 123.4(4) . . ?
C906 C901 C902 114.9(4) . . ?
C906 C901 B02 122.1(3) . . ?
C902 C901 B02 122.7(4) . . ?
F902 C902 C903 117.4(4) . . ?
F902 C902 C901 119.7(4) . . ?
C903 C902 C901 122.9(4) . . ?
F903 C903 C904 119.7(4) . . ?
F903 C903 C902 120.4(4) . . ?
C904 C903 C902 120.0(4) . . ?
F904 C904 C903 120.5(4) . . ?
F904 C904 C905 119.6(4) . . ?
C903 C904 C905 119.8(4) . . ?
F905 C905 C904 120.1(4) . . ?
F905 C905 C906 121.1(4) . . ?
C904 C905 C906 118.8(4) . . ?
F906 C906 C901 119.6(4) . . ?
F906 C906 C905 116.7(4) . . ?
C901 C906 C905 123.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C401 B01 N02 C101 -19.8(5) . . . . ?
C501 B01 N02 C101 159.2(3) . . . . ?
C401 B01 N02 C301 161.7(3) . . . . ?
C501 B01 N02 C301 -19.3(5) . . . . ?
C006 B02 N04 C801 17.7(5) . . . . ?
C901 B02 N04 C801 -163.6(3) . . . . ?
C006 B02 N04 C601 -160.0(3) . . . . ?
C901 B02 N04 C601 18.7(5) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 -177.2(4) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C5 C6 C7 C2 -0.3(7) . . . . ?
C3 C2 C7 C6 -0.6(6) . . . . ?
C1 C2 C7 C6 177.5(4) . . . . ?
C14A C9A C10A C11A 0.0 . . . . ?
C8B C9A C10A C11A 175(2) . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C9A 0.0 . . . . ?
C10A C9A C14A C13A 0.0 . . . . ?
C8B C9A C14A C13A -175(3) . . . . ?
C12B C9B C10B C13B 0.0 . . . . ?
C9B C10B C13B C14B 0.0 . . . . ?
C9B C10B C13B C8A -169.1(19) . . . . ?
C10B C13B C14B C11B 0.0 . . . . ?
C8A C13B C14B C11B 168.9(19) . . . . ?
C13B C14B C11B C12B 0.0 . . . . ?
C14B C11B C12B C9B 0.0 . . . . ?
C10B C9B C12B C11B 0.0 . . . . ?
F002 C002 C003 F003 0.3(6) . . . . ?
C006 C002 C003 F003 -179.3(4) . . . . ?
F002 C002 C003 C004 -179.9(4) . . . . ?
C006 C002 C003 C004 0.5(7) . . . . ?
F003 C003 C004 F004 0.8(7) . . . . ?
C002 C003 C004 F004 -179.0(4) . . . . ?
F003 C003 C004 C005 -179.5(4) . . . . ?
C002 C003 C004 C005 0.7(7) . . . . ?
F004 C004 C005 F005 -0.1(7) . . . . ?
C003 C004 C005 F005 -179.8(4) . . . . ?
F004 C004 C005 C001 178.2(4) . . . . ?
C003 C004 C005 C001 -1.5(8) . . . . ?
F006 C001 C005 F005 -3.0(6) . . . . ?
C006 C001 C005 F005 179.5(4) . . . . ?
F006 C001 C005 C004 178.7(4) . . . . ?
C006 C001 C005 C004 1.2(7) . . . . ?
F006 C001 C006 C002 -177.4(4) . . . . ?
C005 C001 C006 C002 0.0(6) . . . . ?
F006 C001 C006 B02 -4.8(6) . . . . ?
C005 C001 C006 B02 172.6(4) . . . . ?
F002 C002 C006 C001 179.6(4) . . . . ?
C003 C002 C006 C001 -0.8(6) . . . . ?
F002 C002 C006 B02 6.8(6) . . . . ?
C003 C002 C006 B02 -173.5(4) . . . . ?
N04 B02 C006 C001 51.1(6) . . . . ?
C901 B02 C006 C001 -127.6(4) . . . . ?
N04 B02 C006 C002 -136.7(4) . . . . ?
C901 B02 C006 C002 44.5(5) . . . . ?
B01 N02 C101 C114 122.7(4) . . . . ?
C301 N02 C101 C114 -58.7(4) . . . . ?
B01 N02 C101 C102 -57.5(4) . . . . ?
C301 N02 C101 C102 121.1(3) . . . . ?
C114 C101 C102 C107 1.1(5) . . . . ?
N02 C101 C102 C107 -178.6(3) . . . . ?
C114 C101 C102 C103 178.7(3) . . . . ?
N02 C101 C102 C103 -1.0(5) . . . . ?
C107 C102 C103 C104 -0.7(5) . . . . ?
C101 C102 C103 C104 -178.3(3) . . . . ?
C102 C103 C104 C105 0.1(6) . . . . ?
C103 C104 C105 C106 -0.2(6) . . . . ?
C104 C105 C106 C107 0.8(6) . . . . ?
C105 C106 C107 C102 -1.3(5) . . . . ?
C105 C106 C107 C108 179.9(3) . . . . ?
C103 C102 C107 C106 1.3(5) . . . . ?
C101 C102 C107 C106 179.0(3) . . . . ?
C103 C102 C107 C108 -179.9(3) . . . . ?
C101 C102 C107 C108 -2.2(5) . . . . ?
C106 C107 C108 C109 1.1(5) . . . . ?
C102 C107 C108 C109 -177.6(4) . . . . ?
C106 C107 C108 C113 178.7(3) . . . . ?
C102 C107 C108 C113 -0.1(5) . . . . ?
C113 C108 C109 C110 -0.2(6) . . . . ?
C107 C108 C109 C110 177.4(4) . . . . ?
C108 C109 C110 C111 -2.7(7) . . . . ?
C109 C110 C111 C112 1.8(6) . . . . ?
C110 C111 C112 C113 1.8(6) . . . . ?
C109 C108 C113 C112 3.7(5) . . . . ?
C107 C108 C113 C112 -173.9(3) . . . . ?
C109 C108 C113 C114 -178.9(3) . . . . ?
C107 C108 C113 C114 3.5(5) . . . . ?
C111 C112 C113 C108 -4.6(5) . . . . ?
C111 C112 C113 C114 178.1(3) . . . . ?
C102 C101 C114 N01 176.9(3) . . . . ?
N02 C101 C114 N01 -3.4(5) . . . . ?
C102 C101 C114 C113 2.3(5) . . . . ?
N02 C101 C114 C113 -177.9(3) . . . . ?
C201 N01 C114 C101 145.1(4) . . . . ?
C201 N01 C114 C113 -40.4(5) . . . . ?
C108 C113 C114 C101 -4.7(5) . . . . ?
C112 C113 C114 C101 172.7(3) . . . . ?
C108 C113 C114 N01 -179.1(3) . . . . ?
C112 C113 C114 N01 -1.8(5) . . . . ?
C114 N01 C201 C206 -37.2(6) . . . . ?
C114 N01 C201 C202 144.2(4) . . . . ?
C206 C201 C202 C203 2.8(6) . . . . ?
N01 C201 C202 C203 -178.7(3) . . . . ?
C206 C201 C202 C01 -178.1(4) . . . . ?
N01 C201 C202 C01 0.5(5) . . . . ?
C201 C202 C203 C204 0.9(6) . . . . ?
C01 C202 C203 C204 -178.3(4) . . . . ?
C202 C203 C204 C205 -2.7(6) . . . . ?
C203 C204 C205 C206 0.8(6) . . . . ?
C204 C205 C206 C201 2.7(6) . . . . ?
C204 C205 C206 C02 -176.3(4) . . . . ?
C202 C201 C206 C205 -4.5(6) . . . . ?
N01 C201 C206 C205 177.0(3) . . . . ?
C202 C201 C206 C02 174.5(4) . . . . ?
N01 C201 C206 C02 -4.0(6) . . . . ?
B01 N02 C301 C302 -56.6(4) . . . . ?
C101 N02 C301 C302 124.8(3) . . . . ?
B01 N02 C301 C306 125.7(4) . . . . ?
C101 N02 C301 C306 -52.8(4) . . . . ?
C306 C301 C302 C303 0.9(5) . . . . ?
N02 C301 C302 C303 -176.8(3) . . . . ?
C306 C301 C302 C03 179.9(3) . . . . ?
N02 C301 C302 C03 2.2(5) . . . . ?
C301 C302 C303 C304 -0.4(5) . . . . ?
C03 C302 C303 C304 -179.5(3) . . . . ?
C302 C303 C304 C305 -0.1(6) . . . . ?
C303 C304 C305 C306 0.2(6) . . . . ?
C304 C305 C306 C301 0.3(6) . . . . ?
C304 C305 C306 C04 -178.0(4) . . . . ?
C302 C301 C306 C305 -0.8(5) . . . . ?
N02 C301 C306 C305 176.8(3) . . . . ?
C302 C301 C306 C04 177.4(3) . . . . ?
N02 C301 C306 C04 -5.0(5) . . . . ?
N02 B01 C401 C402 -54.6(5) . . . . ?
C501 B01 C401 C402 126.3(4) . . . . ?
N02 B01 C401 C406 130.3(4) . . . . ?
C501 B01 C401 C406 -48.8(5) . . . . ?
C406 C401 C402 F402 177.7(3) . . . . ?
B01 C401 C402 F402 2.2(6) . . . . ?
C406 C401 C402 C403 0.4(6) . . . . ?
B01 C401 C402 C403 -175.0(4) . . . . ?
F402 C402 C403 F403 2.6(6) . . . . ?
C401 C402 C403 F403 179.9(4) . . . . ?
F402 C402 C403 C404 -178.6(4) . . . . ?
C401 C402 C403 C404 -1.3(7) . . . . ?
F403 C403 C404 F404 0.6(7) . . . . ?
C402 C403 C404 F404 -178.3(4) . . . . ?
F403 C403 C404 C405 180.0(4) . . . . ?
C402 C403 C404 C405 1.1(7) . . . . ?
F404 C404 C405 F405 -0.2(7) . . . . ?
C403 C404 C405 F405 -179.6(4) . . . . ?
F404 C404 C405 C406 179.2(4) . . . . ?
C403 C404 C405 C406 -0.2(7) . . . . ?
F405 C405 C406 F406 -0.3(6) . . . . ?
C404 C405 C406 F406 -179.7(4) . . . . ?
F405 C405 C406 C401 178.7(4) . . . . ?
C404 C405 C406 C401 -0.6(7) . . . . ?
C402 C401 C406 F406 179.6(3) . . . . ?
B01 C401 C406 F406 -4.9(5) . . . . ?
C402 C401 C406 C405 0.5(6) . . . . ?
B01 C401 C406 C405 176.1(4) . . . . ?
N02 B01 C501 C502 136.9(4) . . . . ?
C401 B01 C501 C502 -44.0(5) . . . . ?
N02 B01 C501 C506 -51.4(5) . . . . ?
C401 B01 C501 C506 127.7(4) . . . . ?
C506 C501 C502 F502 -180.0(3) . . . . ?
B01 C501 C502 F502 -7.7(5) . . . . ?
C506 C501 C502 C503 0.8(6) . . . . ?
B01 C501 C502 C503 173.1(4) . . . . ?
F502 C502 C503 F503 0.2(6) . . . . ?
C501 C502 C503 F503 179.5(4) . . . . ?
F502 C502 C503 C504 179.2(4) . . . . ?
C501 C502 C503 C504 -1.5(6) . . . . ?
F503 C503 C504 F504 -1.0(7) . . . . ?
C502 C503 C504 F504 -180.0(4) . . . . ?
F503 C503 C504 C505 179.7(4) . . . . ?
C502 C503 C504 C505 0.8(7) . . . . ?
F504 C504 C505 F505 0.1(7) . . . . ?
C503 C504 C505 F505 179.4(4) . . . . ?
F504 C504 C505 C506 -178.6(4) . . . . ?
C503 C504 C505 C506 0.7(7) . . . . ?
F505 C505 C506 F506 2.3(6) . . . . ?
C504 C505 C506 F506 -179.0(4) . . . . ?
F505 C505 C506 C501 179.8(4) . . . . ?
C504 C505 C506 C501 -1.5(7) . . . . ?
C502 C501 C506 F506 178.2(3) . . . . ?
B01 C501 C506 F506 5.9(5) . . . . ?
C502 C501 C506 C505 0.8(6) . . . . ?
B01 C501 C506 C505 -171.5(4) . . . . ?
B02 N04 C601 C614 -123.5(4) . . . . ?
C801 N04 C601 C614 58.7(4) . . . . ?
B02 N04 C601 C602 58.4(4) . . . . ?
C801 N04 C601 C602 -119.4(4) . . . . ?
C614 C601 C602 C607 0.7(5) . . . . ?
N04 C601 C602 C607 178.7(3) . . . . ?
C614 C601 C602 C603 -177.0(3) . . . . ?
N04 C601 C602 C603 1.0(5) . . . . ?
C607 C602 C603 C604 -1.5(6) . . . . ?
C601 C602 C603 C604 176.3(4) . . . . ?
C602 C603 C604 C605 0.5(6) . . . . ?
C603 C604 C605 C606 0.3(6) . . . . ?
C604 C605 C606 C607 -0.1(6) . . . . ?
C605 C606 C607 C602 -1.0(6) . . . . ?
C605 C606 C607 C608 178.8(4) . . . . ?
C603 C602 C607 C606 1.7(5) . . . . ?
C601 C602 C607 C606 -176.2(3) . . . . ?
C603 C602 C607 C608 -178.1(3) . . . . ?
C601 C602 C607 C608 4.1(5) . . . . ?
C606 C607 C608 C613 177.2(3) . . . . ?
C602 C607 C608 C613 -3.0(5) . . . . ?
C606 C607 C608 C609 -5.8(6) . . . . ?
C602 C607 C608 C609 173.9(4) . . . . ?
C613 C608 C609 C610 0.9(6) . . . . ?
C607 C608 C609 C610 -176.1(4) . . . . ?
C608 C609 C610 C611 1.5(6) . . . . ?
C609 C610 C611 C612 -1.2(6) . . . . ?
C610 C611 C612 C613 -1.4(6) . . . . ?
C609 C608 C613 C612 -3.4(5) . . . . ?
C607 C608 C613 C612 173.7(3) . . . . ?
C609 C608 C613 C614 -179.7(3) . . . . ?
C607 C608 C613 C614 -2.7(5) . . . . ?
C611 C612 C613 C608 3.7(6) . . . . ?
C611 C612 C613 C614 180.0(4) . . . . ?
C602 C601 C614 N03 -179.6(3) . . . . ?
N04 C601 C614 N03 2.5(5) . . . . ?
C602 C601 C614 C613 -6.4(5) . . . . ?
N04 C601 C614 C613 175.6(3) . . . . ?
C701 N03 C614 C601 -145.3(4) . . . . ?
C701 N03 C614 C613 41.6(5) . . . . ?
C608 C613 C614 C601 7.4(5) . . . . ?
C612 C613 C614 C601 -168.9(3) . . . . ?
C608 C613 C614 N03 -179.4(3) . . . . ?
C612 C613 C614 N03 4.4(5) . . . . ?
C614 N03 C701 C706 -142.9(4) . . . . ?
C614 N03 C701 C702 37.9(6) . . . . ?
C706 C701 C702 C703 3.4(5) . . . . ?
N03 C701 C702 C703 -177.4(3) . . . . ?
C706 C701 C702 C06 -175.1(4) . . . . ?
N03 C701 C702 C06 4.1(6) . . . . ?
C701 C702 C703 C704 -2.9(6) . . . . ?
C06 C702 C703 C704 175.7(4) . . . . ?
C702 C703 C704 C705 0.4(6) . . . . ?
C703 C704 C705 C706 1.6(6) . . . . ?
C704 C705 C706 C701 -1.1(6) . . . . ?
C704 C705 C706 C05 178.7(4) . . . . ?
C702 C701 C706 C705 -1.5(5) . . . . ?
N03 C701 C706 C705 179.3(3) . . . . ?
C702 C701 C706 C05 178.7(3) . . . . ?
N03 C701 C706 C05 -0.5(5) . . . . ?
B02 N04 C801 C806 -123.5(4) . . . . ?
C601 N04 C801 C806 54.3(4) . . . . ?
B02 N04 C801 C802 57.2(5) . . . . ?
C601 N04 C801 C802 -125.1(3) . . . . ?
C806 C801 C802 C803 -1.0(5) . . . . ?
N04 C801 C802 C803 178.4(3) . . . . ?
C806 C801 C802 C07 -179.5(3) . . . . ?
N04 C801 C802 C07 -0.2(5) . . . . ?
C801 C802 C803 C804 0.1(5) . . . . ?
C07 C802 C803 C804 178.8(3) . . . . ?
C802 C803 C804 C805 0.4(6) . . . . ?
C803 C804 C805 C806 0.0(6) . . . . ?
C804 C805 C806 C801 -0.8(5) . . . . ?
C804 C805 C806 C08 177.3(3) . . . . ?
C802 C801 C806 C805 1.3(5) . . . . ?
N04 C801 C806 C805 -178.0(3) . . . . ?
C802 C801 C806 C08 -176.6(3) . . . . ?
N04 C801 C806 C08 4.0(5) . . . . ?
N04 B02 C901 C906 -130.6(4) . . . . ?
C006 B02 C901 C906 48.2(5) . . . . ?
N04 B02 C901 C902 56.0(5) . . . . ?
C006 B02 C901 C902 -125.3(4) . . . . ?
C906 C901 C902 F902 -178.0(3) . . . . ?
B02 C901 C902 F902 -4.1(5) . . . . ?
C906 C901 C902 C903 1.0(6) . . . . ?
B02 C901 C902 C903 174.9(4) . . . . ?
F902 C902 C903 F903 -1.5(6) . . . . ?
C901 C902 C903 F903 179.6(4) . . . . ?
F902 C902 C903 C904 179.3(4) . . . . ?
C901 C902 C903 C904 0.3(6) . . . . ?
F903 C903 C904 F904 -1.3(7) . . . . ?
C902 C903 C904 F904 177.9(4) . . . . ?
F903 C903 C904 C905 179.9(4) . . . . ?
C902 C903 C904 C905 -0.9(7) . . . . ?
F904 C904 C905 F905 0.1(6) . . . . ?
C903 C904 C905 F905 179.0(4) . . . . ?
F904 C904 C905 C906 -178.7(4) . . . . ?
C903 C904 C905 C906 0.1(6) . . . . ?
C902 C901 C906 F906 -179.6(3) . . . . ?
B02 C901 C906 F906 6.5(5) . . . . ?
C902 C901 C906 C905 -1.8(6) . . . . ?
B02 C901 C906 C905 -175.7(4) . . . . ?
F905 C905 C906 F906 0.3(5) . . . . ?
C904 C905 C906 F906 179.1(3) . . . . ?
F905 C905 C906 C901 -177.6(3) . . . . ?
C904 C905 C906 C901 1.3(6) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_compound_17
_database_code_depnum_ccdc_archive 'CCDC 1535321'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-03-28 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         ?
_chemical_formula_sum            'C34 H22 B F5 N2'
_chemical_formula_weight         564.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   10.3922(19)
_cell_length_b                   19.522(3)
_cell_length_c                   39.998(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8115(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6096
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      22.25

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             3480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72097
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         1.018
_diffrn_reflns_theta_max         27.637
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9400
_reflns_number_gt                5227
_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       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_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)+(0.0482P)²+3.1085P] 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         9400
_refine_ls_number_parameters     573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
B01 B 0.5788(3) 0.46431(13) 0.58211(6) 0.0249(6) Uani 1 1 d . . . . .
B02 B 0.5000 0.18346(19) 0.7500 0.0259(9) Uani 1 2 d S T P . .
N01 N 0.45626(18) 0.46740(9) 0.59722(4) 0.0227(4) Uani 1 1 d . . . . .
N02 N 0.59177(18) 0.52415(9) 0.56197(4) 0.0226(4) Uani 1 1 d . . . . .
N03 N 0.58955(18) 0.22696(9) 0.73376(4) 0.0238(4) Uani 1 1 d . . . . .
F402 F 0.55462(15) 0.32266(7) 0.56024(4) 0.0482(4) Uani 1 1 d . . . . .
F403 F 0.72523(17) 0.22323(7) 0.57313(4) 0.0593(5) Uani 1 1 d . . . . .
F404 F 0.94377(15) 0.25238(8) 0.60710(4) 0.0564(5) Uani 1 1 d . . . . .
F405 F 0.98653(14) 0.38172(8) 0.62974(4) 0.0515(4) Uani 1 1 d . . . . .
F406 F 0.81490(13) 0.48123(6) 0.61736(3) 0.0380(4) Uani 1 1 d . . . . .
F802 F 0.33290(17) 0.09796(8) 0.71058(4) 0.0580(5) Uani 1 1 d . . . . .
F803 F 0.3357(2) -0.04008(9) 0.70996(5) 0.0849(7) Uani 1 1 d . . . . .
F804 F 0.5000 -0.10943(10) 0.7500 0.0898(11) Uani 1 2 d S T P . .
C01 C 0.2284(3) 0.24791(16) 0.67185(8) 0.0657(10) Uani 1 1 d . . . . .
H01A H 0.2665 0.2462 0.6943 0.098 Uiso 1 1 calc R U . . .
H01B H 0.2441 0.2044 0.6603 0.098 Uiso 1 1 calc R U . . .
H01C H 0.1356 0.2557 0.6737 0.098 Uiso 1 1 calc R U . . .
C02 C 0.9922(3) 0.58384(14) 0.46756(7) 0.0427(7) Uani 1 1 d . . . . .
H02A H 1.0000 0.5462 0.4515 0.064 Uiso 1 1 calc R U . . .
H02B H 1.0749 0.5908 0.4788 0.064 Uiso 1 1 calc R U . . .
H02C H 0.9677 0.6259 0.4558 0.064 Uiso 1 1 calc R U . . .
C03 C 0.9905(3) 0.11136(13) 0.65373(7) 0.0398(7) Uani 1 1 d . . . . .
H03A H 0.9570 0.0681 0.6449 0.060 Uiso 1 1 calc R U . . .
H03B H 1.0660 0.1022 0.6677 0.060 Uiso 1 1 calc R U . . .
H03C H 1.0151 0.1413 0.6351 0.060 Uiso 1 1 calc R U . . .
C101 C 0.4771(2) 0.56259(11) 0.56517(5) 0.0201(5) Uani 1 1 d . . . . .
C102 C 0.4420(2) 0.62643(11) 0.54984(5) 0.0221(5) Uani 1 1 d . . . . .
C103 C 0.5213(2) 0.66366(11) 0.52768(6) 0.0301(6) Uani 1 1 d . . . . .
H103 H 0.6053 0.6472 0.5228 0.036 Uiso 1 1 calc R U . . .
C104 C 0.4791(3) 0.72322(12) 0.51302(6) 0.0381(6) Uani 1 1 d . . . . .
H104 H 0.5343 0.7476 0.4983 0.046 Uiso 1 1 calc R U . . .
C105 C 0.3574(3) 0.74784(13) 0.51950(6) 0.0407(7) Uani 1 1 d . . . . .
H105 H 0.3275 0.7882 0.5087 0.049 Uiso 1 1 calc R U . . .
C106 C 0.2801(3) 0.71381(12) 0.54155(6) 0.0341(6) Uani 1 1 d . . . . .
H106 H 0.1968 0.7317 0.5461 0.041 Uiso 1 1 calc R U . . .
C107 C 0.3191(2) 0.65314(11) 0.55783(5) 0.0254(5) Uani 1 1 d . . . . .
C108 C 0.2371(2) 0.61929(11) 0.58215(5) 0.0231(5) Uani 1 1 d . . . . .
C109 C 0.1188(2) 0.64795(12) 0.59208(6) 0.0321(6) Uani 1 1 d . . . . .
H109 H 0.0912 0.6897 0.5822 0.038 Uiso 1 1 calc R U . . .
C110 C 0.0428(2) 0.61721(13) 0.61552(6) 0.0349(6) Uani 1 1 d . . . . .
H110 H -0.0370 0.6375 0.6215 0.042 Uiso 1 1 calc R U . . .
C111 C 0.0815(2) 0.55630(13) 0.63069(6) 0.0340(6) Uani 1 1 d . . . . .
H111 H 0.0286 0.5353 0.6471 0.041 Uiso 1 1 calc R U . . .
C112 C 0.1961(2) 0.52683(12) 0.62179(6) 0.0299(6) Uani 1 1 d . . . . .
H112 H 0.2224 0.4855 0.6323 0.036 Uiso 1 1 calc R U . . .
C113 C 0.2759(2) 0.55669(11) 0.59728(5) 0.0221(5) Uani 1 1 d . . . . .
C114 C 0.3964(2) 0.52846(10) 0.58684(5) 0.0208(5) Uani 1 1 d . . . . .
C201 C 0.3985(2) 0.41295(11) 0.61628(5) 0.0232(5) Uani 1 1 d . . . . .
C202 C 0.4301(2) 0.40346(13) 0.64927(6) 0.0360(6) Uani 1 1 d . . . . .
H202 H 0.4899 0.4332 0.6599 0.043 Uiso 1 1 calc R U . . .
C203 C 0.3746(3) 0.35040(14) 0.66703(7) 0.0449(7) Uani 1 1 d . . . . .
H203 H 0.3958 0.3446 0.6900 0.054 Uiso 1 1 calc R U . . .
C204 C 0.2888(2) 0.30554(13) 0.65224(6) 0.0377(6) Uani 1 1 d . . . . .
C205 C 0.2595(2) 0.31545(12) 0.61886(6) 0.0320(6) Uani 1 1 d . . . . .
H205 H 0.2014 0.2851 0.6081 0.038 Uiso 1 1 calc R U . . .
C206 C 0.3131(2) 0.36854(11) 0.60097(6) 0.0272(5) Uani 1 1 d . . . . .
H206 H 0.2914 0.3747 0.5781 0.033 Uiso 1 1 calc R U . . .
C301 C 0.6947(2) 0.53761(10) 0.53892(5) 0.0209(5) Uani 1 1 d . . . . .
C302 C 0.6878(2) 0.51277(12) 0.50668(5) 0.0282(5) Uani 1 1 d . . . . .
H302 H 0.6165 0.4856 0.5000 0.034 Uiso 1 1 calc R U . . .
C303 C 0.7847(2) 0.52742(12) 0.48411(6) 0.0321(6) Uani 1 1 d . . . . .
H303 H 0.7785 0.5104 0.4619 0.039 Uiso 1 1 calc R U . . .
C304 C 0.8904(2) 0.56631(11) 0.49313(6) 0.0273(5) Uani 1 1 d . . . . .
C305 C 0.8980(2) 0.58837(11) 0.52610(6) 0.0284(5) Uani 1 1 d . . . . .
H305 H 0.9712 0.6137 0.5331 0.034 Uiso 1 1 calc R U . . .
C306 C 0.8016(2) 0.57440(11) 0.54888(5) 0.0253(5) Uani 1 1 d . . . . .
H306 H 0.8087 0.5900 0.5713 0.030 Uiso 1 1 calc R U . . .
C401 C 0.7919(2) 0.41778(11) 0.60528(6) 0.0268(5) Uani 1 1 d . . . . .
C402 C 0.6620(2) 0.33908(12) 0.57729(6) 0.0320(6) Uani 1 1 d . . . . .
C403 C 0.7486(3) 0.28748(12) 0.58352(6) 0.0369(6) Uani 1 1 d . . . . .
C404 C 0.8582(3) 0.30206(12) 0.60087(6) 0.0360(6) Uani 1 1 d . . . . .
C405 C 0.8803(2) 0.36744(13) 0.61212(6) 0.0328(6) Uani 1 1 d . . . . .
C406 C 0.6800(2) 0.40602(11) 0.58762(5) 0.0249(5) Uani 1 1 d . . . . .
C501 C 0.5546(2) 0.29546(10) 0.74014(5) 0.0213(5) Uani 1 1 d . . . . .
C502 C 0.6131(2) 0.35788(11) 0.72879(5) 0.0234(5) Uani 1 1 d . . . . .
C503 C 0.7213(2) 0.36028(12) 0.70751(6) 0.0285(5) Uani 1 1 d . . . . .
H503 H 0.7605 0.3187 0.7006 0.034 Uiso 1 1 calc R U . . .
C504 C 0.7710(2) 0.42139(12) 0.69664(6) 0.0322(6) Uani 1 1 d . . . . .
H504 H 0.8444 0.4218 0.6825 0.039 Uiso 1 1 calc R U . . .
C505 C 0.7141(2) 0.48263(12) 0.70626(6) 0.0352(6) Uani 1 1 d . . . . .
H505 H 0.7477 0.5249 0.6984 0.042 Uiso 1 1 calc R U . . .
C506 C 0.6097(2) 0.48208(12) 0.72707(6) 0.0334(6) Uani 1 1 d . . . . .
H506 H 0.5725 0.5244 0.7337 0.040 Uiso 1 1 calc R U . . .
C507 C 0.5557(2) 0.42048(11) 0.73904(5) 0.0253(5) Uani 1 1 d . . . . .
C601 C 0.6933(2) 0.20289(10) 0.71337(5) 0.0226(5) Uani 1 1 d . . . . .
C602 C 0.8126(2) 0.19140(11) 0.72692(6) 0.0286(6) Uani 1 1 d . . . . .
H602 H 0.8286 0.2025 0.7497 0.034 Uiso 1 1 calc R U . . .
C603 C 0.9097(2) 0.16362(12) 0.70747(6) 0.0302(6) Uani 1 1 d . . . . .
H603 H 0.9924 0.1566 0.7170 0.036 Uiso 1 1 calc R U . . .
C604 C 0.8885(2) 0.14585(11) 0.67436(6) 0.0266(5) Uani 1 1 d . . . . .
C605 C 0.7693(2) 0.15873(13) 0.66122(6) 0.0364(6) Uani 1 1 d . . . . .
H605 H 0.7534 0.1480 0.6384 0.044 Uiso 1 1 calc R U . . .
C606 C 0.6713(2) 0.18699(13) 0.68023(6) 0.0337(6) Uani 1 1 d . . . . .
H606 H 0.5894 0.1954 0.6705 0.040 Uiso 1 1 calc R U . . .
C801 C 0.5000 0.10275(16) 0.7500 0.0303(8) Uani 1 2 d S T P . .
C802 C 0.4179(3) 0.06501(13) 0.73029(7) 0.0415(7) Uani 1 1 d . . . . .
C803 C 0.4173(3) -0.00582(14) 0.72979(8) 0.0542(9) Uani 1 1 d . . . . .
C804 C 0.5000 -0.04075(19) 0.7500 0.0583(14) Uani 1 2 d S T P . .


_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
B01 N01 1.411(3) . ?
B01 N02 1.425(3) . ?
B01 C406 1.566(3) . ?
B02 N03 1.417(3) . ?
B02 N03 1.418(3) 3_656 ?
B02 C801 1.576(5) . ?
N01 C114 1.407(3) . ?
N01 C201 1.439(3) . ?
N02 C101 1.414(3) . ?
N02 C301 1.437(3) . ?
N03 C501 1.409(3) . ?
N03 C601 1.431(3) . ?
F402 C402 1.347(3) . ?
F403 C403 1.343(3) . ?
F404 C404 1.339(3) . ?
F405 C405 1.339(3) . ?
F406 C401 1.351(2) . ?
F802 C802 1.347(3) . ?
F803 C803 1.340(4) . ?
F804 C804 1.341(4) . ?
C01 C204 1.508(3) . ?
C02 C304 1.511(3) . ?
C03 C604 1.503(3) . ?
C101 C114 1.378(3) . ?
C101 C102 1.436(3) . ?
C102 C103 1.412(3) . ?
C102 C107 1.416(3) . ?
C103 C104 1.374(3) . ?
C104 C105 1.378(4) . ?
C105 C106 1.366(3) . ?
C106 C107 1.411(3) . ?
C107 C108 1.452(3) . ?
C108 C109 1.408(3) . ?
C108 C113 1.422(3) . ?
C109 C110 1.365(3) . ?
C110 C111 1.394(3) . ?
C111 C112 1.370(3) . ?
C112 C113 1.410(3) . ?
C113 C114 1.430(3) . ?
C201 C202 1.372(3) . ?
C201 C206 1.384(3) . ?
C202 C203 1.382(3) . ?
C203 C204 1.383(4) . ?
C204 C205 1.383(3) . ?
C205 C206 1.377(3) . ?
C301 C302 1.380(3) . ?
C301 C306 1.381(3) . ?
C302 C303 1.382(3) . ?
C303 C304 1.383(3) . ?
C304 C305 1.389(3) . ?
C305 C306 1.382(3) . ?
C401 C405 1.373(3) . ?
C401 C406 1.380(3) . ?
C402 C403 1.374(3) . ?
C402 C406 1.383(3) . ?
C403 C404 1.364(4) . ?
C404 C405 1.373(4) . ?
C501 C501 1.382(4) 3_656 ?
C501 C502 1.436(3) . ?
C502 C503 1.411(3) . ?
C502 C507 1.420(3) . ?
C503 C504 1.371(3) . ?
C504 C505 1.388(3) . ?
C505 C506 1.367(3) . ?
C506 C507 1.411(3) . ?
C507 C507 1.452(5) 3_656 ?
C601 C602 1.372(3) . ?
C601 C606 1.380(3) . ?
C602 C603 1.385(3) . ?
C603 C604 1.387(3) . ?
C604 C605 1.369(3) . ?
C605 C606 1.386(3) . ?
C801 C802 1.376(3) 3_656 ?
C801 C802 1.376(3) . ?
C802 C803 1.383(4) . ?
C803 C804 1.362(4) . ?
C804 C803 1.362(4) 3_656 ?

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
N01 B01 N02 107.0(2) . . ?
N01 B01 C406 125.3(2) . . ?
N02 B01 C406 127.7(2) . . ?
N03 B02 N03 106.4(3) . 3_656 ?
N03 B02 C801 126.80(14) . . ?
N03 B02 C801 126.80(14) 3_656 . ?
C114 N01 B01 107.99(18) . . ?
C114 N01 C201 126.70(18) . . ?
B01 N01 C201 124.87(19) . . ?
C101 N02 B01 107.69(18) . . ?
C101 N02 C301 126.06(17) . . ?
B01 N02 C301 125.67(19) . . ?
C501 N03 B02 108.44(19) . . ?
C501 N03 C601 127.52(18) . . ?
B02 N03 C601 123.99(19) . . ?
C114 C101 N02 108.26(18) . . ?
C114 C101 C102 122.3(2) . . ?
N02 C101 C102 129.48(19) . . ?
C103 C102 C107 118.6(2) . . ?
C103 C102 C101 124.5(2) . . ?
C107 C102 C101 116.9(2) . . ?
C104 C103 C102 121.1(2) . . ?
C103 C104 C105 120.5(2) . . ?
C106 C105 C104 119.5(2) . . ?
C105 C106 C107 122.5(2) . . ?
C106 C107 C102 117.7(2) . . ?
C106 C107 C108 121.5(2) . . ?
C102 C107 C108 120.8(2) . . ?
C109 C108 C113 118.0(2) . . ?
C109 C108 C107 121.4(2) . . ?
C113 C108 C107 120.6(2) . . ?
C110 C109 C108 121.6(2) . . ?
C109 C110 C111 120.5(2) . . ?
C112 C111 C110 119.7(2) . . ?
C111 C112 C113 121.2(2) . . ?
C112 C113 C108 119.0(2) . . ?
C112 C113 C114 124.0(2) . . ?
C108 C113 C114 117.07(19) . . ?
C101 C114 N01 109.04(19) . . ?
C101 C114 C113 122.02(19) . . ?
N01 C114 C113 128.84(19) . . ?
C202 C201 C206 119.6(2) . . ?
C202 C201 N01 120.6(2) . . ?
C206 C201 N01 119.73(19) . . ?
C201 C202 C203 119.7(2) . . ?
C202 C203 C204 121.6(2) . . ?
C203 C204 C205 117.8(2) . . ?
C203 C204 C01 121.2(2) . . ?
C205 C204 C01 121.0(2) . . ?
C206 C205 C204 121.2(2) . . ?
C205 C206 C201 120.1(2) . . ?
C302 C301 C306 119.6(2) . . ?
C302 C301 N02 119.8(2) . . ?
C306 C301 N02 120.59(19) . . ?
C301 C302 C303 120.0(2) . . ?
C302 C303 C304 121.4(2) . . ?
C303 C304 C305 117.6(2) . . ?
C303 C304 C02 120.2(2) . . ?
C305 C304 C02 122.2(2) . . ?
C306 C305 C304 121.6(2) . . ?
C301 C306 C305 119.7(2) . . ?
F406 C401 C405 117.8(2) . . ?
F406 C401 C406 119.0(2) . . ?
C405 C401 C406 123.2(2) . . ?
F402 C402 C403 117.4(2) . . ?
F402 C402 C406 119.2(2) . . ?
C403 C402 C406 123.3(2) . . ?
F403 C403 C404 120.2(2) . . ?
F403 C403 C402 120.7(2) . . ?
C404 C403 C402 119.1(2) . . ?
F404 C404 C403 119.9(2) . . ?
F404 C404 C405 120.1(2) . . ?
C403 C404 C405 120.0(2) . . ?
F405 C405 C401 120.5(2) . . ?
F405 C405 C404 120.3(2) . . ?
C401 C405 C404 119.2(2) . . ?
C401 C406 C402 115.1(2) . . ?
C401 C406 B01 121.2(2) . . ?
C402 C406 B01 123.6(2) . . ?
C501 C501 N03 108.37(12) 3_656 . ?
C501 C501 C502 121.88(13) 3_656 . ?
N03 C501 C502 129.7(2) . . ?
C503 C502 C507 118.7(2) . . ?
C503 C502 C501 123.8(2) . . ?
C507 C502 C501 117.5(2) . . ?
C504 C503 C502 121.4(2) . . ?
C503 C504 C505 120.1(2) . . ?
C506 C505 C504 120.0(2) . . ?
C505 C506 C507 121.9(2) . . ?
C506 C507 C502 117.9(2) . . ?
C506 C507 C507 121.48(14) . 3_656 ?
C502 C507 C507 120.60(13) . 3_656 ?
C602 C601 C606 119.5(2) . . ?
C602 C601 N03 120.63(19) . . ?
C606 C601 N03 119.8(2) . . ?
C601 C602 C603 120.0(2) . . ?
C602 C603 C604 121.3(2) . . ?
C605 C604 C603 117.7(2) . . ?
C605 C604 C03 120.6(2) . . ?
C603 C604 C03 121.7(2) . . ?
C604 C605 C606 121.8(2) . . ?
C601 C606 C605 119.7(2) . . ?
C802 C801 C802 115.2(3) 3_656 . ?
C802 C801 B02 122.38(16) 3_656 . ?
C802 C801 B02 122.38(16) . . ?
F802 C802 C801 119.1(2) . . ?
F802 C802 C803 117.8(3) . . ?
C801 C802 C803 123.1(3) . . ?
F803 C803 C804 120.0(2) . . ?
F803 C803 C802 120.7(3) . . ?
C804 C803 C802 119.3(3) . . ?
F804 C804 C803 120.03(18) . 3_656 ?
F804 C804 C803 120.03(18) . . ?
C803 C804 C803 119.9(4) 3_656 . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.054

