# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1576561'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2017-11-27 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 H26 N2'
_chemical_formula_weight         390.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   6.4301(2)
_cell_length_b                   13.8923(3)
_cell_length_c                   12.2241(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.031(2)
_cell_angle_gamma                90
_cell_volume                     1063.84(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3992
_cell_measurement_theta_min      4.8760
_cell_measurement_theta_max      74.1390

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    0.541
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75467
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_reflns_number            6768
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.891
_diffrn_reflns_theta_max         74.066
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2123
_reflns_number_gt                1905
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.2705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2123
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.88622(17) 0.84978(8) 0.40074(9) 0.0165(2) Uani 1 1 d . . . . .
C2 C 1.11214(17) 0.85230(8) 0.41709(9) 0.0182(2) Uani 1 1 d . . . . .
H2 H 1.1850 0.8010 0.3904 0.022 Uiso 1 1 calc R U . . .
C3 C 0.77599(17) 1.07170(8) 0.52903(9) 0.0180(2) Uani 1 1 d . . . . .
H3 H 0.6250 1.0696 0.5176 0.022 Uiso 1 1 calc R U . . .
C4 C 0.88749(16) 0.99594(8) 0.49027(8) 0.0155(2) Uani 1 1 d . . . . .
C5 C 0.76268(17) 0.76495(8) 0.34646(9) 0.0174(2) Uani 1 1 d . . . . .
C6 C 0.60505(18) 0.72772(8) 0.39643(10) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.5748 0.7593 0.4600 0.025 Uiso 1 1 calc R U . . .
C7 C 0.49169(19) 0.64553(8) 0.35504(10) 0.0241(3) Uani 1 1 d . . . . .
H7 H 0.3850 0.6211 0.3901 0.029 Uiso 1 1 calc R U . . .
C8 C 0.53531(19) 0.59938(9) 0.26213(10) 0.0254(3) Uani 1 1 d . . . . .
H8 H 0.4591 0.5429 0.2333 0.030 Uiso 1 1 calc R U . . .
C9 C 0.69056(19) 0.63608(8) 0.21160(10) 0.0238(3) Uani 1 1 d . . . . .
H9 H 0.7197 0.6037 0.1482 0.029 Uiso 1 1 calc R U . . .
C10 C 0.80577(17) 0.71927(8) 0.25091(9) 0.0192(3) Uani 1 1 d . . . . .
C11 C 0.96548(18) 0.75371(8) 0.18895(9) 0.0217(3) Uani 1 1 d . . . . .
H11 H 1.0721 0.7088 0.1804 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9763(2) 0.84035(9) 0.14400(10) 0.0252(3) Uani 1 1 d . . . . .
C13 C 0.8213(2) 0.92032(9) 0.14688(11) 0.0321(3) Uani 1 1 d . . . . .
H13A H 0.7018 0.8959 0.1764 0.048 Uiso 1 1 calc R U . . .
H13B H 0.7675 0.9452 0.0707 0.048 Uiso 1 1 calc R U . . .
H13C H 0.8933 0.9721 0.1954 0.048 Uiso 1 1 calc R U . . .
C14 C 1.1495(3) 0.86431(11) 0.08423(13) 0.0398(4) Uani 1 1 d . . . . .
H14A H 1.2487 0.8100 0.0904 0.060 Uiso 1 1 calc R U . . .
H14B H 1.2268 0.9215 0.1184 0.060 Uiso 1 1 calc R U . . .
H14C H 1.0861 0.8771 0.0049 0.060 Uiso 1 1 calc R U . . .
N1 N 0.77642(14) 0.91922(6) 0.43634(7) 0.0167(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
C1 N1 1.3255(14) . ?
C1 C2 1.4215(15) . ?
C1 C5 1.4907(14) . ?
C2 C3 1.3610(15) 3_776 ?
C2 H2 0.9500 . ?
C3 C2 1.3611(15) 3_776 ?
C3 C4 1.4140(15) . ?
C3 H3 0.9500 . ?
C4 N1 1.3669(14) . ?
C4 C4 1.417(2) 3_776 ?
C5 C6 1.3954(16) . ?
C5 C10 1.4106(16) . ?
C6 C7 1.3873(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3869(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3842(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3982(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4859(16) . ?
C11 C12 1.3315(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4981(18) . ?
C12 C14 1.5006(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 C1 C2 122.62(10) . . ?
N1 C1 C5 116.84(9) . . ?
C2 C1 C5 120.48(9) . . ?
C3 C2 C1 119.93(10) 3_776 . ?
C3 C2 H2 120.0 3_776 . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.15(10) 3_776 . ?
C2 C3 H3 120.4 3_776 . ?
C4 C3 H3 120.4 . . ?
N1 C4 C3 119.52(9) . . ?
N1 C4 C4 123.08(12) . 3_776 ?
C3 C4 C4 117.39(12) . 3_776 ?
C6 C5 C10 119.56(10) . . ?
C6 C5 C1 117.71(10) . . ?
C10 C5 C1 122.66(10) . . ?
C7 C6 C5 121.28(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 119.51(11) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 119.64(11) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 122.05(11) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C5 117.95(10) . . ?
C9 C10 C11 117.68(10) . . ?
C5 C10 C11 124.37(10) . . ?
C12 C11 C10 127.44(11) . . ?
C12 C11 H11 116.3 . . ?
C10 C11 H11 116.3 . . ?
C11 C12 C13 124.32(11) . . ?
C11 C12 C14 121.00(12) . . ?
C13 C12 C14 114.68(11) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C4 117.82(9) . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.048



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1576563'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2017-11-27 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 H54 B2 N2'
_chemical_formula_weight         584.47

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'

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

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

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

_cell_length_a                   9.0141(7)
_cell_length_b                   12.9277(10)
_cell_length_c                   15.5179(9)
_cell_angle_alpha                111.750(6)
_cell_angle_beta                 98.849(6)
_cell_angle_gamma                99.031(7)
_cell_volume                     1613.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4289
_cell_measurement_theta_min      3.9790
_cell_measurement_theta_max      29.2090

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_reflns_number            16240
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.881
_diffrn_reflns_theta_max         29.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7575
_reflns_number_gt                5569
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+0.6732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7575
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2994(2) -0.00858(16) 0.77814(13) 0.0250(4) Uani 1 1 d . . . . .
C2 C 0.2170(2) -0.09120(17) 0.80153(14) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.1983 -0.1698 0.7601 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1618(2) -0.06103(17) 0.88398(14) 0.0319(4) Uani 1 1 d . . . . .
H3 H 0.1040 -0.1187 0.8977 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1906(2) 0.05306(17) 0.94655(14) 0.0310(4) Uani 1 1 d . . . . .
H4 H 0.1554 0.0734 1.0039 0.037 Uiso 1 1 calc R U . . .
C5 C 0.2706(2) 0.13669(17) 0.92482(13) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.2891 0.2150 0.9669 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3247(2) 0.10645(15) 0.84084(12) 0.0237(4) Uani 1 1 d . . . . .
C7 C 0.3691(2) -0.03878(16) 0.69177(13) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.3857 -0.1174 0.6786 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2567(2) -0.05147(18) 0.59973(13) 0.0321(5) Uani 1 1 d . . . . .
H8 H 0.3138 -0.0721 0.5477 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2064(2) 0.05732(19) 0.60443(14) 0.0355(5) Uani 1 1 d . . . . .
H9A H 0.1571 0.0844 0.6581 0.053 Uiso 1 1 calc R U . . .
H9B H 0.1328 0.0410 0.5449 0.053 Uiso 1 1 calc R U . . .
H9C H 0.2968 0.1165 0.6133 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1136(3) -0.1494(2) 0.56864(16) 0.0449(6) Uani 1 1 d . . . . .
H10A H 0.0540 -0.1611 0.5060 0.067 Uiso 1 1 calc R U . . .
H10B H 0.0495 -0.1301 0.6153 0.067 Uiso 1 1 calc R U . . .
H10C H 0.1456 -0.2198 0.5646 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6536(2) 0.03306(17) 0.81045(13) 0.0292(4) Uani 1 1 d . . . . .
H11 H 0.6029 0.0522 0.8655 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6651(3) -0.09320(19) 0.77801(16) 0.0381(5) Uani 1 1 d . . . . .
H12A H 0.5666 -0.1388 0.7787 0.046 Uiso 1 1 calc R U . . .
H12B H 0.7472 -0.0978 0.8258 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6993(3) -0.15047(18) 0.67834(16) 0.0389(5) Uani 1 1 d . . . . .
H13A H 0.8127 -0.1351 0.6859 0.047 Uiso 1 1 calc R U . . .
H13B H 0.6607 -0.2343 0.6551 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6299(3) -0.11269(18) 0.60127(15) 0.0357(5) Uani 1 1 d . . . . .
H14A H 0.5207 -0.1551 0.5738 0.043 Uiso 1 1 calc R U . . .
H14B H 0.6857 -0.1337 0.5494 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6374(2) 0.01675(16) 0.63836(13) 0.0273(4) Uani 1 1 d . . . . .
H15 H 0.5828 0.0334 0.5855 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8085(2) 0.08348(18) 0.66939(15) 0.0346(5) Uani 1 1 d . . . . .
H16A H 0.8608 0.0458 0.6187 0.041 Uiso 1 1 calc R U . . .
H16B H 0.8109 0.1616 0.6724 0.041 Uiso 1 1 calc R U . . .
C17 C 0.9037(3) 0.0949(2) 0.76466(16) 0.0393(5) Uani 1 1 d . . . . .
H17A H 0.9402 0.0239 0.7549 0.047 Uiso 1 1 calc R U . . .
H17B H 0.9957 0.1590 0.7864 0.047 Uiso 1 1 calc R U . . .
C18 C 0.8125(2) 0.11599(19) 0.84215(15) 0.0372(5) Uani 1 1 d . . . . .
H18A H 0.7984 0.1953 0.8630 0.045 Uiso 1 1 calc R U . . .
H18B H 0.8736 0.1094 0.8978 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4037(2) 0.19673(15) 0.81689(12) 0.0226(4) Uani 1 1 d . . . . .
C20 C 0.3684(2) 0.30259(15) 0.84559(12) 0.0240(4) Uani 1 1 d . . . . .
H20 H 0.2913 0.3165 0.8811 0.029 Uiso 1 1 calc R U . . .
C21 C 0.4421(2) 0.38918(15) 0.82413(12) 0.0224(4) Uani 1 1 d . . . . .
C22 C 0.5711(2) 0.25983(15) 0.73873(12) 0.0229(4) Uani 1 1 d . . . . .
H22 H 0.6400 0.2431 0.6975 0.027 Uiso 1 1 calc R U . . .
C23 C 0.4390(2) 0.57747(15) 0.81439(12) 0.0241(4) Uani 1 1 d . . . . .
C24 C 0.4049(2) 0.68477(17) 0.85269(14) 0.0299(4) Uani 1 1 d . . . . .
H24 H 0.4262 0.7370 0.8238 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3412(2) 0.71712(17) 0.93148(14) 0.0316(4) Uani 1 1 d . . . . .
H25 H 0.3186 0.7905 0.9559 0.038 Uiso 1 1 calc R U . . .
C26 C 0.3102(2) 0.64242(17) 0.97466(13) 0.0301(4) Uani 1 1 d . . . . .
H26 H 0.2663 0.6643 1.0287 0.036 Uiso 1 1 calc R U . . .
C27 C 0.3431(2) 0.53647(16) 0.93918(13) 0.0270(4) Uani 1 1 d . . . . .
H27 H 0.3214 0.4852 0.9689 0.032 Uiso 1 1 calc R U . . .
C28 C 0.4084(2) 0.50311(15) 0.85957(12) 0.0232(4) Uani 1 1 d . . . . .
C29 C 0.5145(2) 0.54339(16) 0.73092(12) 0.0253(4) Uani 1 1 d . . . . .
H29 H 0.5746 0.6173 0.7343 0.030 Uiso 1 1 calc R U . . .
C30 C 0.3954(2) 0.49137(18) 0.63259(13) 0.0316(4) Uani 1 1 d . . . . .
H30 H 0.4569 0.4784 0.5827 0.038 Uiso 1 1 calc R U . . .
C31 C 0.2896(3) 0.37594(19) 0.60971(15) 0.0392(5) Uani 1 1 d . . . . .
H31A H 0.2191 0.3498 0.5471 0.059 Uiso 1 1 calc R U . . .
H31B H 0.2297 0.3838 0.6585 0.059 Uiso 1 1 calc R U . . .
H31C H 0.3518 0.3200 0.6088 0.059 Uiso 1 1 calc R U . . .
C32 C 0.2984(3) 0.5742(2) 0.62095(16) 0.0468(6) Uani 1 1 d . . . . .
H32A H 0.2376 0.5433 0.5551 0.070 Uiso 1 1 calc R U . . .
H32B H 0.3666 0.6484 0.6357 0.070 Uiso 1 1 calc R U . . .
H32C H 0.2289 0.5841 0.6646 0.070 Uiso 1 1 calc R U . . .
C33 C 0.7784(2) 0.54597(17) 0.84607(13) 0.0282(4) Uani 1 1 d . . . . .
H33 H 0.7275 0.5647 0.9011 0.034 Uiso 1 1 calc R U . . .
C34 C 0.8931(2) 0.4729(2) 0.85850(16) 0.0380(5) Uani 1 1 d . . . . .
H34A H 0.9720 0.5183 0.9186 0.046 Uiso 1 1 calc R U . . .
H34B H 0.8365 0.4050 0.8650 0.046 Uiso 1 1 calc R U . . .
C35 C 0.9750(3) 0.4320(2) 0.77727(19) 0.0454(6) Uani 1 1 d . . . . .
H35A H 1.0267 0.3725 0.7844 0.054 Uiso 1 1 calc R U . . .
H35B H 1.0565 0.4972 0.7838 0.054 Uiso 1 1 calc R U . . .
C36 C 0.8710(3) 0.38291(19) 0.67653(17) 0.0394(5) Uani 1 1 d . . . . .
H36A H 0.8269 0.3006 0.6582 0.047 Uiso 1 1 calc R U . . .
H36B H 0.9361 0.3885 0.6318 0.047 Uiso 1 1 calc R U . . .
C37 C 0.7377(2) 0.44043(16) 0.66324(14) 0.0304(4) Uani 1 1 d . . . . .
H37 H 0.6623 0.3895 0.6018 0.036 Uiso 1 1 calc R U . . .
C38 C 0.8044(2) 0.55525(17) 0.65750(14) 0.0320(4) Uani 1 1 d . . . . .
H38A H 0.8636 0.5397 0.6072 0.038 Uiso 1 1 calc R U . . .
H38B H 0.7175 0.5861 0.6379 0.038 Uiso 1 1 calc R U . . .
C39 C 0.9100(2) 0.64745(17) 0.75090(14) 0.0332(5) Uani 1 1 d . . . . .
H39A H 0.9211 0.7223 0.7459 0.040 Uiso 1 1 calc R U . . .
H39B H 1.0136 0.6306 0.7569 0.040 Uiso 1 1 calc R U . . .
C40 C 0.8566(2) 0.65918(17) 0.84292(14) 0.0321(4) Uani 1 1 d . . . . .
H40A H 0.7834 0.7098 0.8518 0.038 Uiso 1 1 calc R U . . .
H40B H 0.9474 0.6975 0.8974 0.038 Uiso 1 1 calc R U . . .
N1 N 0.50887(18) 0.17547(13) 0.76150(10) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.54632(17) 0.36576(13) 0.76810(10) 0.0230(3) Uani 1 1 d . . . . .
B1 B 0.5427(2) 0.04333(17) 0.72198(14) 0.0231(4) Uani 1 1 d . . . . .
B2 B 0.6450(2) 0.47392(17) 0.74785(15) 0.0243(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
C1 C2 1.395(3) . ?
C1 C6 1.401(3) . ?
C1 C7 1.514(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C6 C19 1.466(3) . ?
C7 C8 1.556(3) . ?
C7 B1 1.637(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.525(3) . ?
C8 C10 1.531(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C18 1.535(3) . ?
C11 C12 1.546(3) . ?
C11 B1 1.630(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.551(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.536(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.541(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.549(3) . ?
C15 B1 1.623(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.534(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N1 1.368(2) . ?
C19 C20 1.379(3) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 N2 1.370(2) . ?
C21 C28 1.468(2) . ?
C22 N1 1.336(2) . ?
C22 N2 1.341(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(3) . ?
C23 C28 1.403(3) . ?
C23 C29 1.510(2) . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.373(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.403(2) . ?
C27 H27 0.9500 . ?
C29 C30 1.563(3) . ?
C29 B2 1.634(3) . ?
C29 H29 1.0000 . ?
C30 C31 1.523(3) . ?
C30 C32 1.527(3) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.542(3) . ?
C33 C40 1.543(3) . ?
C33 B2 1.634(3) . ?
C33 H33 1.0000 . ?
C34 C35 1.526(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.534(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.536(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.552(3) . ?
C37 B2 1.624(3) . ?
C37 H37 1.0000 . ?
C38 C39 1.538(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.539(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
N1 B1 1.683(2) . ?
N2 B2 1.693(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.72(17) . . ?
C2 C1 C7 122.75(16) . . ?
C6 C1 C7 119.43(16) . . ?
C3 C2 C1 121.39(17) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.30(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.56(17) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.19(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.82(17) . . ?
C1 C6 C19 119.72(16) . . ?
C5 C6 C19 119.42(16) . . ?
C1 C7 C8 113.45(15) . . ?
C1 C7 B1 108.93(14) . . ?
C8 C7 B1 118.42(16) . . ?
C1 C7 H7 104.9 . . ?
C8 C7 H7 104.9 . . ?
B1 C7 H7 104.9 . . ?
C9 C8 C10 109.23(18) . . ?
C9 C8 C7 114.86(16) . . ?
C10 C8 C7 112.48(18) . . ?
C9 C8 H8 106.6 . . ?
C10 C8 H8 106.6 . . ?
C7 C8 H8 106.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C18 C11 C12 112.26(17) . . ?
C18 C11 B1 111.76(17) . . ?
C12 C11 B1 107.29(16) . . ?
C18 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
B1 C11 H11 108.5 . . ?
C11 C12 C13 116.92(17) . . ?
C11 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
C11 C12 H12B 108.1 . . ?
C13 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C14 C13 C12 116.40(17) . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 C15 113.69(17) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 109.24(16) . . ?
C14 C15 B1 105.52(15) . . ?
C16 C15 B1 115.53(16) . . ?
C14 C15 H15 108.8 . . ?
C16 C15 H15 108.8 . . ?
B1 C15 H15 108.8 . . ?
C17 C16 C15 117.51(17) . . ?
C17 C16 H16A 107.9 . . ?
C15 C16 H16A 107.9 . . ?
C17 C16 H16B 107.9 . . ?
C15 C16 H16B 107.9 . . ?
H16A C16 H16B 107.2 . . ?
C18 C17 C16 112.82(18) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C11 113.86(17) . . ?
C17 C18 H18A 108.8 . . ?
C11 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C11 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
N1 C19 C20 118.64(16) . . ?
N1 C19 C6 120.35(16) . . ?
C20 C19 C6 120.93(16) . . ?
C19 C20 C21 121.87(16) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
N2 C21 C20 118.39(16) . . ?
N2 C21 C28 120.63(16) . . ?
C20 C21 C28 120.98(16) . . ?
N1 C22 N2 126.63(16) . . ?
N1 C22 H22 116.7 . . ?
N2 C22 H22 116.7 . . ?
C24 C23 C28 117.66(16) . . ?
C24 C23 C29 122.09(17) . . ?
C28 C23 C29 120.16(16) . . ?
C25 C24 C23 121.81(18) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C26 C25 C24 119.86(18) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 119.84(17) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.70(18) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C23 C28 C27 120.11(17) . . ?
C23 C28 C21 120.98(16) . . ?
C27 C28 C21 118.90(16) . . ?
C23 C29 C30 112.77(15) . . ?
C23 C29 B2 110.22(15) . . ?
C30 C29 B2 118.27(15) . . ?
C23 C29 H29 104.7 . . ?
C30 C29 H29 104.7 . . ?
B2 C29 H29 104.7 . . ?
C31 C30 C32 109.52(19) . . ?
C31 C30 C29 114.92(16) . . ?
C32 C30 C29 112.35(16) . . ?
C31 C30 H30 106.5 . . ?
C32 C30 H30 106.5 . . ?
C29 C30 H30 106.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C40 113.05(17) . . ?
C34 C33 B2 110.27(16) . . ?
C40 C33 B2 108.29(15) . . ?
C34 C33 H33 108.4 . . ?
C40 C33 H33 108.4 . . ?
B2 C33 H33 108.4 . . ?
C35 C34 C33 114.85(17) . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34B 108.6 . . ?
C33 C34 H34B 108.6 . . ?
H34A C34 H34B 107.5 . . ?
C34 C35 C36 115.34(19) . . ?
C34 C35 H35A 108.4 . . ?
C36 C35 H35A 108.4 . . ?
C34 C35 H35B 108.4 . . ?
C36 C35 H35B 108.4 . . ?
H35A C35 H35B 107.5 . . ?
C35 C36 C37 115.95(18) . . ?
C35 C36 H36A 108.3 . . ?
C37 C36 H36A 108.3 . . ?
C35 C36 H36B 108.3 . . ?
C37 C36 H36B 108.3 . . ?
H36A C36 H36B 107.4 . . ?
C36 C37 C38 108.33(17) . . ?
C36 C37 B2 116.72(17) . . ?
C38 C37 B2 105.28(15) . . ?
C36 C37 H37 108.8 . . ?
C38 C37 H37 108.8 . . ?
B2 C37 H37 108.8 . . ?
C39 C38 C37 114.76(16) . . ?
C39 C38 H38A 108.6 . . ?
C37 C38 H38A 108.6 . . ?
C39 C38 H38B 108.6 . . ?
C37 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?
C38 C39 C40 116.21(16) . . ?
C38 C39 H39A 108.2 . . ?
C40 C39 H39A 108.2 . . ?
C38 C39 H39B 108.2 . . ?
C40 C39 H39B 108.2 . . ?
H39A C39 H39B 107.4 . . ?
C39 C40 C33 115.54(16) . . ?
C39 C40 H40A 108.4 . . ?
C33 C40 H40A 108.4 . . ?
C39 C40 H40B 108.4 . . ?
C33 C40 H40B 108.4 . . ?
H40A C40 H40B 107.5 . . ?
C22 N1 C19 117.20(15) . . ?
C22 N1 B1 124.82(14) . . ?
C19 N1 B1 117.88(14) . . ?
C22 N2 C21 117.11(15) . . ?
C22 N2 B2 124.35(14) . . ?
C21 N2 B2 118.36(14) . . ?
C15 B1 C11 104.92(15) . . ?
C15 B1 C7 115.08(15) . . ?
C11 B1 C7 112.32(16) . . ?
C15 B1 N1 114.46(15) . . ?
C11 B1 N1 107.68(14) . . ?
C7 B1 N1 102.39(14) . . ?
C37 B2 C33 105.20(16) . . ?
C37 B2 C29 112.90(16) . . ?
C33 B2 C29 113.58(15) . . ?
C37 B2 N2 117.67(14) . . ?
C33 B2 N2 103.97(14) . . ?
C29 B2 N2 103.47(14) . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.311
_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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1576562'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2017-11-27 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 H54 B2 N2'
_chemical_formula_weight         584.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.2519(2)
_cell_length_b                   10.4002(1)
_cell_length_c                   18.7527(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.829(1)
_cell_angle_gamma                90
_cell_volume                     3352.73(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10796
_cell_measurement_theta_min      4.7130
_cell_measurement_theta_max      73.6030

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.484
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_reflns_number            23298
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.344
_diffrn_reflns_theta_max         74.114
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6718
_reflns_number_gt                5754
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0789P)²+2.5274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6718
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.56133(10) 0.01707(17) 0.75163(9) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.62921(11) -0.0228(2) 0.79125(11) 0.0371(4) Uani 1 1 d . . . . .
H2 H 0.6568 0.0372 0.8220 0.045 Uiso 1 1 calc R U . . .
C3 C 0.65769(12) -0.1464(2) 0.78722(12) 0.0444(5) Uani 1 1 d . . . . .
H3 H 0.7037 -0.1703 0.8154 0.053 Uiso 1 1 calc R U . . .
C4 C 0.61938(12) -0.2355(2) 0.74218(13) 0.0439(5) Uani 1 1 d . . . . .
H4 H 0.6389 -0.3206 0.7394 0.053 Uiso 1 1 calc R U . . .
C5 C 0.55245(11) -0.19937(18) 0.70128(11) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.5263 -0.2600 0.6699 0.041 Uiso 1 1 calc R U . . .
C6 C 0.52275(9) -0.07465(16) 0.70563(9) 0.0249(3) Uani 1 1 d . . . . .
C7 C 0.53242(10) 0.15380(17) 0.75462(9) 0.0285(4) Uani 1 1 d . . . . .
H7 H 0.5802 0.2073 0.7653 0.034 Uiso 1 1 calc R U . . .
C8 C 0.48031(12) 0.1823(2) 0.81647(11) 0.0413(5) Uani 1 1 d . . . . .
H8 H 0.4659 0.2752 0.8119 0.050 Uiso 1 1 calc R U . . .
C9 C 0.40562(15) 0.1104(3) 0.81468(14) 0.0644(8) Uani 1 1 d . . . . .
H9A H 0.4161 0.0178 0.8138 0.097 Uiso 1 1 calc R U . . .
H9B H 0.3725 0.1346 0.7717 0.097 Uiso 1 1 calc R U . . .
H9C H 0.3790 0.1314 0.8574 0.097 Uiso 1 1 calc R U . . .
C10 C 0.52383(18) 0.1677(5) 0.88923(14) 0.1053(16) Uani 1 1 d . . . . .
H10A H 0.4938 0.2074 0.9255 0.158 Uiso 1 1 calc R U . . .
H10B H 0.5746 0.2102 0.8893 0.158 Uiso 1 1 calc R U . . .
H10C H 0.5314 0.0762 0.9001 0.158 Uiso 1 1 calc R U . . .
C11 C 0.56149(10) 0.18129(17) 0.61532(10) 0.0293(4) Uani 1 1 d . . . . .
H11 H 0.5818 0.0912 0.6181 0.035 Uiso 1 1 calc R U . . .
C12 C 0.63005(11) 0.27308(19) 0.63573(12) 0.0393(5) Uani 1 1 d . . . . .
H12A H 0.6643 0.2741 0.5960 0.047 Uiso 1 1 calc R U . . .
H12B H 0.6606 0.2375 0.6782 0.047 Uiso 1 1 calc R U . . .
C13 C 0.60820(12) 0.4133(2) 0.65235(14) 0.0460(5) Uani 1 1 d . . . . .
H13A H 0.6527 0.4536 0.6808 0.055 Uiso 1 1 calc R U . . .
H13B H 0.6001 0.4610 0.6066 0.055 Uiso 1 1 calc R U . . .
C14 C 0.53512(12) 0.42884(18) 0.69321(13) 0.0419(5) Uani 1 1 d . . . . .
H14A H 0.5184 0.5199 0.6905 0.050 Uiso 1 1 calc R U . . .
H14B H 0.5487 0.4080 0.7443 0.050 Uiso 1 1 calc R U . . .
C15 C 0.46597(10) 0.34304(17) 0.66464(11) 0.0316(4) Uani 1 1 d . . . . .
H15 H 0.4222 0.3554 0.6958 0.038 Uiso 1 1 calc R U . . .
C16 C 0.43773(12) 0.38202(19) 0.58710(12) 0.0407(5) Uani 1 1 d . . . . .
H16A H 0.3843 0.3485 0.5765 0.049 Uiso 1 1 calc R U . . .
H16B H 0.4347 0.4770 0.5850 0.049 Uiso 1 1 calc R U . . .
C17 C 0.48733(14) 0.3362(2) 0.52759(12) 0.0463(5) Uani 1 1 d . . . . .
H17A H 0.4544 0.3357 0.4817 0.056 Uiso 1 1 calc R U . . .
H17B H 0.5297 0.3991 0.5230 0.056 Uiso 1 1 calc R U . . .
C18 C 0.52321(12) 0.2032(2) 0.53954(10) 0.0377(4) Uani 1 1 d . . . . .
H18A H 0.5628 0.1903 0.5049 0.045 Uiso 1 1 calc R U . . .
H18B H 0.4821 0.1377 0.5294 0.045 Uiso 1 1 calc R U . . .
C19 C 0.45001(9) -0.04051(15) 0.66386(8) 0.0215(3) Uani 1 1 d . . . . .
C20 C 0.39765(9) -0.13052(16) 0.63381(8) 0.0227(3) Uani 1 1 d . . . . .
H20 H 0.4115 -0.2189 0.6349 0.027 Uiso 1 1 calc R U . . .
C21 C 0.32527(9) -0.09390(16) 0.60216(8) 0.0230(3) Uani 1 1 d . . . . .
C22 C 0.35924(9) 0.11558(16) 0.63005(8) 0.0236(3) Uani 1 1 d . . . . .
H22 H 0.3457 0.2041 0.6284 0.028 Uiso 1 1 calc R U . . .
C23 C 0.21050(10) -0.1351(2) 0.51581(10) 0.0335(4) Uani 1 1 d . . . . .
C24 C 0.16367(12) -0.2263(2) 0.47770(11) 0.0444(5) Uani 1 1 d . . . . .
H24 H 0.1222 -0.1971 0.4452 0.053 Uiso 1 1 calc R U . . .
C25 C 0.17560(13) -0.3568(2) 0.48562(12) 0.0456(5) Uani 1 1 d . . . . .
H25 H 0.1423 -0.4154 0.4590 0.055 Uiso 1 1 calc R U . . .
C26 C 0.23575(13) -0.4028(2) 0.53198(11) 0.0403(5) Uani 1 1 d . . . . .
H26 H 0.2442 -0.4927 0.5374 0.048 Uiso 1 1 calc R U . . .
C27 C 0.28335(11) -0.31622(18) 0.57025(10) 0.0320(4) Uani 1 1 d . . . . .
H27 H 0.3249 -0.3472 0.6021 0.038 Uiso 1 1 calc R U . . .
C28 C 0.27156(10) -0.18305(17) 0.56296(9) 0.0271(4) Uani 1 1 d . . . . .
C29 C 0.19361(12) 0.0068(2) 0.50875(11) 0.0398(5) Uani 1 1 d . . . . .
H29 H 0.1358 0.0128 0.4995 0.048 Uiso 1 1 calc R U . . .
C30 C 0.22593(16) 0.0706(2) 0.44383(12) 0.0529(6) Uani 1 1 d . . . . .
H30 H 0.2056 0.1607 0.4423 0.063 Uiso 1 1 calc R U . . .
C31 C 0.1966(2) 0.0086(3) 0.37205(13) 0.0814(10) Uani 1 1 d . . . . .
H31A H 0.2116 0.0624 0.3326 0.122 Uiso 1 1 calc R U . . .
H31B H 0.1398 0.0009 0.3693 0.122 Uiso 1 1 calc R U . . .
H31C H 0.2198 -0.0770 0.3686 0.122 Uiso 1 1 calc R U . . .
C32 C 0.31105(17) 0.0812(3) 0.44754(13) 0.0617(7) Uani 1 1 d . . . . .
H32A H 0.3343 -0.0038 0.4566 0.093 Uiso 1 1 calc R U . . .
H32B H 0.3290 0.1398 0.4864 0.093 Uiso 1 1 calc R U . . .
H32C H 0.3267 0.1148 0.4021 0.093 Uiso 1 1 calc R U . . .
C33 C 0.16243(11) 0.0206(2) 0.64904(12) 0.0393(5) Uani 1 1 d . . . . .
H33 H 0.1693 -0.0748 0.6513 0.047 Uiso 1 1 calc R U . . .
C34 C 0.07534(12) 0.0501(3) 0.62792(16) 0.0598(7) Uani 1 1 d . . . . .
H34A H 0.0570 -0.0069 0.5877 0.072 Uiso 1 1 calc R U . . .
H34B H 0.0452 0.0283 0.6689 0.072 Uiso 1 1 calc R U . . .
C35 C 0.05688(13) 0.1909(3) 0.60572(17) 0.0659(8) Uani 1 1 d . . . . .
H35A H 0.0055 0.1929 0.5780 0.079 Uiso 1 1 calc R U . . .
H35B H 0.0527 0.2424 0.6496 0.079 Uiso 1 1 calc R U . . .
C36 C 0.11651(13) 0.2558(3) 0.56103(12) 0.0500(6) Uani 1 1 d . . . . .
H36A H 0.1068 0.3496 0.5601 0.060 Uiso 1 1 calc R U . . .
H36B H 0.1085 0.2239 0.5112 0.060 Uiso 1 1 calc R U . . .
C37 C 0.20195(11) 0.23166(19) 0.58917(10) 0.0333(4) Uani 1 1 d . . . . .
H37 H 0.2365 0.2725 0.5555 0.040 Uiso 1 1 calc R U . . .
C38 C 0.21773(12) 0.2954(2) 0.66349(11) 0.0380(4) Uani 1 1 d . . . . .
H38A H 0.2746 0.3064 0.6732 0.046 Uiso 1 1 calc R U . . .
H38B H 0.1942 0.3822 0.6613 0.046 Uiso 1 1 calc R U . . .
C39 C 0.18727(14) 0.2231(2) 0.72679(12) 0.0486(5) Uani 1 1 d . . . . .
H39A H 0.2178 0.2507 0.7712 0.058 Uiso 1 1 calc R U . . .
H39B H 0.1326 0.2488 0.7308 0.058 Uiso 1 1 calc R U . . .
C40 C 0.19085(13) 0.0771(2) 0.72204(11) 0.0438(5) Uani 1 1 d . . . . .
H40A H 0.1591 0.0403 0.7586 0.053 Uiso 1 1 calc R U . . .
H40B H 0.2453 0.0495 0.7340 0.053 Uiso 1 1 calc R U . . .
N1 N 0.43143(8) 0.08642(13) 0.65498(7) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.30425(8) 0.03220(14) 0.60724(7) 0.0235(3) Uani 1 1 d . . . . .
B1 B 0.49810(11) 0.19662(18) 0.67445(10) 0.0241(4) Uani 1 1 d . . . . .
B2 B 0.21353(11) 0.0767(2) 0.58620(11) 0.0303(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
C1 C2 1.396(3) . ?
C1 C6 1.414(2) . ?
C1 C7 1.510(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C19 1.466(2) . ?
C7 C8 1.555(3) . ?
C7 B1 1.631(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.488(3) . ?
C8 C10 1.508(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C18 1.533(3) . ?
C11 C12 1.543(3) . ?
C11 B1 1.629(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.545(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.549(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.548(3) . ?
C15 B1 1.626(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.538(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.524(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N1 1.365(2) . ?
C19 C20 1.387(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C21 N2 1.366(2) . ?
C21 C28 1.464(2) . ?
C22 N1 1.328(2) . ?
C22 N2 1.329(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(3) . ?
C23 C28 1.408(3) . ?
C23 C29 1.508(3) . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.379(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.405(3) . ?
C27 H27 0.9500 . ?
C29 C30 1.532(3) . ?
C29 B2 1.635(3) . ?
C29 H29 1.0000 . ?
C30 C32 1.468(4) . ?
C30 C31 1.539(3) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C40 1.532(3) . ?
C33 C34 1.552(3) . ?
C33 B2 1.637(3) . ?
C33 H33 1.0000 . ?
C34 C35 1.549(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.536(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.544(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.546(3) . ?
C37 B2 1.625(3) . ?
C37 H37 1.0000 . ?
C38 C39 1.535(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.523(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
N1 B1 1.643(2) . ?
N2 B2 1.648(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
C2 C1 C6 117.07(17) . . ?
C2 C1 C7 121.65(16) . . ?
C6 C1 C7 121.21(15) . . ?
C3 C2 C1 122.26(18) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 120.20(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.36(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.78(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.33(16) . . ?
C5 C6 C19 119.63(15) . . ?
C1 C6 C19 120.01(15) . . ?
C1 C7 C8 114.88(16) . . ?
C1 C7 B1 108.57(14) . . ?
C8 C7 B1 116.61(15) . . ?
C1 C7 H7 105.2 . . ?
C8 C7 H7 105.2 . . ?
B1 C7 H7 105.2 . . ?
C9 C8 C10 109.5(2) . . ?
C9 C8 C7 116.22(18) . . ?
C10 C8 C7 112.38(19) . . ?
C9 C8 H8 106.0 . . ?
C10 C8 H8 106.0 . . ?
C7 C8 H8 106.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C18 C11 C12 113.54(16) . . ?
C18 C11 B1 110.78(15) . . ?
C12 C11 B1 108.36(15) . . ?
C18 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
B1 C11 H11 108.0 . . ?
C11 C12 C13 116.05(16) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 115.07(16) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 C15 114.02(17) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 110.27(16) . . ?
C16 C15 B1 115.39(15) . . ?
C14 C15 B1 104.78(15) . . ?
C16 C15 H15 108.7 . . ?
C14 C15 H15 108.7 . . ?
B1 C15 H15 108.7 . . ?
C17 C16 C15 116.75(17) . . ?
C17 C16 H16A 108.1 . . ?
C15 C16 H16A 108.1 . . ?
C17 C16 H16B 108.1 . . ?
C15 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C16 114.71(16) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C11 114.17(17) . . ?
C17 C18 H18A 108.7 . . ?
C11 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C11 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
N1 C19 C20 117.69(14) . . ?
N1 C19 C6 118.75(14) . . ?
C20 C19 C6 123.54(15) . . ?
C19 C20 C21 121.30(15) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
N2 C21 C20 117.87(15) . . ?
N2 C21 C28 118.84(15) . . ?
C20 C21 C28 123.28(15) . . ?
N1 C22 N2 125.95(15) . . ?
N1 C22 H22 117.0 . . ?
N2 C22 H22 117.0 . . ?
C24 C23 C28 116.65(19) . . ?
C24 C23 C29 121.23(18) . . ?
C28 C23 C29 122.06(16) . . ?
C25 C24 C23 122.5(2) . . ?
C25 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
C24 C25 C26 120.40(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 118.9(2) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 121.21(19) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C27 C28 C23 120.34(16) . . ?
C27 C28 C21 119.67(16) . . ?
C23 C28 C21 119.93(16) . . ?
C23 C29 C30 114.41(18) . . ?
C23 C29 B2 109.43(16) . . ?
C30 C29 B2 116.74(18) . . ?
C23 C29 H29 105.0 . . ?
C30 C29 H29 105.0 . . ?
B2 C29 H29 105.0 . . ?
C32 C30 C29 115.09(19) . . ?
C32 C30 C31 109.1(2) . . ?
C29 C30 C31 113.5(2) . . ?
C32 C30 H30 106.2 . . ?
C29 C30 H30 106.2 . . ?
C31 C30 H30 106.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C40 C33 C34 112.49(19) . . ?
C40 C33 B2 110.81(16) . . ?
C34 C33 B2 108.32(18) . . ?
C40 C33 H33 108.4 . . ?
C34 C33 H33 108.4 . . ?
B2 C33 H33 108.4 . . ?
C35 C34 C33 115.4(2) . . ?
C35 C34 H34A 108.4 . . ?
C33 C34 H34A 108.4 . . ?
C35 C34 H34B 108.4 . . ?
C33 C34 H34B 108.4 . . ?
H34A C34 H34B 107.5 . . ?
C36 C35 C34 115.45(19) . . ?
C36 C35 H35A 108.4 . . ?
C34 C35 H35A 108.4 . . ?
C36 C35 H35B 108.4 . . ?
C34 C35 H35B 108.4 . . ?
H35A C35 H35B 107.5 . . ?
C35 C36 C37 113.96(19) . . ?
C35 C36 H36A 108.8 . . ?
C37 C36 H36A 108.8 . . ?
C35 C36 H36B 108.8 . . ?
C37 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
C36 C37 C38 109.22(16) . . ?
C36 C37 B2 105.42(17) . . ?
C38 C37 B2 116.28(16) . . ?
C36 C37 H37 108.6 . . ?
C38 C37 H37 108.6 . . ?
B2 C37 H37 108.6 . . ?
C39 C38 C37 116.20(18) . . ?
C39 C38 H38A 108.2 . . ?
C37 C38 H38A 108.2 . . ?
C39 C38 H38B 108.2 . . ?
C37 C38 H38B 108.2 . . ?
H38A C38 H38B 107.4 . . ?
C40 C39 C38 115.14(17) . . ?
C40 C39 H39A 108.5 . . ?
C38 C39 H39A 108.5 . . ?
C40 C39 H39B 108.5 . . ?
C38 C39 H39B 108.5 . . ?
H39A C39 H39B 107.5 . . ?
C39 C40 C33 115.03(19) . . ?
C39 C40 H40A 108.5 . . ?
C33 C40 H40A 108.5 . . ?
C39 C40 H40B 108.5 . . ?
C33 C40 H40B 108.5 . . ?
H40A C40 H40B 107.5 . . ?
C22 N1 C19 117.86(14) . . ?
C22 N1 B1 122.49(13) . . ?
C19 N1 B1 119.65(13) . . ?
C22 N2 C21 117.54(14) . . ?
C22 N2 B2 122.10(14) . . ?
C21 N2 B2 120.36(14) . . ?
C15 B1 C11 104.88(14) . . ?
C15 B1 C7 117.00(15) . . ?
C11 B1 C7 112.84(14) . . ?
C15 B1 N1 113.75(13) . . ?
C11 B1 N1 106.14(13) . . ?
C7 B1 N1 101.97(13) . . ?
C37 B2 C29 117.01(16) . . ?
C37 B2 C33 104.69(15) . . ?
C29 B2 C33 113.28(17) . . ?
C37 B2 N2 112.79(15) . . ?
C29 B2 N2 102.25(14) . . ?
C33 B2 N2 106.59(15) . . ?

_refine_diff_density_max         0.878
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.048



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

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1576564'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2017-11-27 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            'C44 H56 B2 N2'
_chemical_formula_weight         634.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.7137(3)
_cell_length_b                   14.9388(4)
_cell_length_c                   11.2075(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.824(3)
_cell_angle_gamma                90
_cell_volume                     1755.70(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3888
_cell_measurement_theta_min      2.9550
_cell_measurement_theta_max      28.1510

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_reflns_number            9978
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_max         29.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.642
_diffrn_reflns_point_group_measured_fraction_full 0.803
_reflns_number_total             6295
_reflns_number_gt                5474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.463
_reflns_Friedel_fraction_max     0.421
_reflns_Friedel_fraction_full    0.591

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.3597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1519 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   3.1(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         6295
_refine_ls_number_parameters     437
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1643(2) 0.78121(19) -0.1739(2) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.2884(2) 0.8127(2) -0.1236(2) 0.0249(6) Uani 1 1 d . . . . .
H2 H 0.3290 0.8526 -0.1696 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3506(2) 0.7871(2) -0.0109(2) 0.0235(6) Uani 1 1 d . . . . .
H3 H 0.4372 0.8035 0.0182 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2856(2) 0.73610(18) 0.0623(2) 0.0201(6) Uani 1 1 d . . . . .
C5 C 0.2696(2) 0.69450(19) 0.2602(2) 0.0207(6) Uani 1 1 d . . . . .
C6 C 0.1353(2) 0.6946(2) 0.2220(2) 0.0237(6) Uani 1 1 d . . . . .
H6 H 0.0836 0.6893 0.2811 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0791(2) 0.7021(2) 0.1022(2) 0.0237(6) Uani 1 1 d . . . . .
H7 H -0.0105 0.6950 0.0766 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1550(2) 0.72044(19) 0.0167(2) 0.0199(6) Uani 1 1 d . . . . .
C9 C 0.1048(2) 0.80386(19) -0.3018(2) 0.0205(6) Uani 1 1 d . . . . .
C10 C 0.1808(3) 0.8277(2) -0.3839(3) 0.0254(6) Uani 1 1 d . . . . .
H10 H 0.2707 0.8315 -0.3567 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1272(3) 0.8461(2) -0.5042(3) 0.0293(7) Uani 1 1 d . . . . .
H11 H 0.1797 0.8622 -0.5594 0.035 Uiso 1 1 calc R U . . .
C12 C -0.0033(3) 0.8408(2) -0.5435(2) 0.0300(7) Uani 1 1 d . . . . .
H12 H -0.0407 0.8530 -0.6263 0.036 Uiso 1 1 calc R U . . .
C13 C -0.0798(3) 0.8178(2) -0.4629(2) 0.0278(6) Uani 1 1 d . . . . .
H13 H -0.1696 0.8150 -0.4912 0.033 Uiso 1 1 calc R U . . .
C14 C -0.0284(2) 0.79867(18) -0.3407(2) 0.0210(6) Uani 1 1 d . . . . .
C15 C -0.1092(2) 0.76768(19) -0.2536(2) 0.0215(6) Uani 1 1 d . . . . .
H15 H -0.1919 0.7461 -0.3037 0.026 Uiso 1 1 calc R U . . .
C16 C -0.1408(3) 0.84615(19) -0.1727(3) 0.0249(6) Uani 1 1 d . . . . .
H16 H -0.0652 0.8553 -0.1049 0.030 Uiso 1 1 calc R U . . .
C17 C -0.2546(3) 0.8230(2) -0.1159(3) 0.0378(8) Uani 1 1 d . . . . .
H17A H -0.2728 0.8734 -0.0661 0.057 Uiso 1 1 calc R U . . .
H17B H -0.2348 0.7697 -0.0646 0.057 Uiso 1 1 calc R U . . .
H17C H -0.3293 0.8111 -0.1807 0.057 Uiso 1 1 calc R U . . .
C18 C -0.1677(3) 0.9346(2) -0.2416(3) 0.0370(8) Uani 1 1 d . . . . .
H18A H -0.2415 0.9275 -0.3088 0.055 Uiso 1 1 calc R U . . .
H18B H -0.0931 0.9520 -0.2742 0.055 Uiso 1 1 calc R U . . .
H18C H -0.1857 0.9812 -0.1858 0.055 Uiso 1 1 calc R U . . .
C19 C 0.0168(2) 0.61059(19) -0.2751(2) 0.0218(6) Uani 1 1 d . . . . .
H19 H 0.0712 0.6457 -0.3210 0.026 Uiso 1 1 calc R U . . .
C20 C -0.0999(3) 0.5758(2) -0.3689(2) 0.0272(6) Uani 1 1 d . . . . .
H20A H -0.1364 0.6263 -0.4220 0.033 Uiso 1 1 calc R U . . .
H20B H -0.0700 0.5305 -0.4212 0.033 Uiso 1 1 calc R U . . .
C21 C -0.2061(3) 0.5340(2) -0.3135(3) 0.0313(7) Uani 1 1 d . . . . .
H21A H -0.2855 0.5325 -0.3768 0.038 Uiso 1 1 calc R U . . .
H21B H -0.1824 0.4714 -0.2905 0.038 Uiso 1 1 calc R U . . .
C22 C -0.2332(3) 0.5828(2) -0.2018(2) 0.0259(6) Uani 1 1 d . . . . .
H22A H -0.2839 0.5426 -0.1599 0.031 Uiso 1 1 calc R U . . .
H22B H -0.2863 0.6359 -0.2298 0.031 Uiso 1 1 calc R U . . .
C23 C -0.1139(2) 0.61376(19) -0.1082(2) 0.0218(6) Uani 1 1 d . . . . .
H23 H -0.1430 0.6498 -0.0438 0.026 Uiso 1 1 calc R U . . .
C24 C -0.0385(3) 0.5321(2) -0.0466(2) 0.0276(6) Uani 1 1 d . . . . .
H24A H 0.0237 0.5534 0.0256 0.033 Uiso 1 1 calc R U . . .
H24B H -0.0989 0.4917 -0.0170 0.033 Uiso 1 1 calc R U . . .
C25 C 0.0333(3) 0.4776(2) -0.1264(3) 0.0336(7) Uani 1 1 d . . . . .
H25A H 0.0974 0.4395 -0.0734 0.040 Uiso 1 1 calc R U . . .
H25B H -0.0276 0.4376 -0.1797 0.040 Uiso 1 1 calc R U . . .
C26 C 0.1004(3) 0.5358(2) -0.2055(3) 0.0286(6) Uani 1 1 d . . . . .
H26A H 0.1308 0.4970 -0.2653 0.034 Uiso 1 1 calc R U . . .
H26B H 0.1763 0.5634 -0.1531 0.034 Uiso 1 1 calc R U . . .
C27 C 0.3274(2) 0.68000(19) 0.3904(2) 0.0204(6) Uani 1 1 d . . . . .
C28 C 0.2597(2) 0.6341(2) 0.4656(3) 0.0259(6) Uani 1 1 d . . . . .
H28 H 0.1769 0.6117 0.4324 0.031 Uiso 1 1 calc R U . . .
C29 C 0.3118(3) 0.6211(2) 0.5873(3) 0.0287(7) Uani 1 1 d . . . . .
H29 H 0.2652 0.5895 0.6375 0.034 Uiso 1 1 calc R U . . .
C30 C 0.4320(3) 0.6540(2) 0.6361(3) 0.0300(7) Uani 1 1 d . . . . .
H30 H 0.4676 0.6461 0.7203 0.036 Uiso 1 1 calc R U . . .
C31 C 0.5003(2) 0.6983(2) 0.5622(2) 0.0256(6) Uani 1 1 d . . . . .
H31 H 0.5831 0.7203 0.5965 0.031 Uiso 1 1 calc R U . . .
C32 C 0.4508(2) 0.71166(19) 0.4386(2) 0.0204(6) Uani 1 1 d . . . . .
C33 C 0.5273(2) 0.75515(18) 0.3549(2) 0.0191(6) Uani 1 1 d . . . . .
H33 H 0.6193 0.7496 0.3952 0.023 Uiso 1 1 calc R U . . .
C34 C 0.4970(3) 0.8566(2) 0.3405(3) 0.0263(6) Uani 1 1 d . . . . .
H34 H 0.4076 0.8633 0.2932 0.032 Uiso 1 1 calc R U . . .
C35 C 0.5854(4) 0.9052(2) 0.2716(3) 0.0448(9) Uani 1 1 d . . . . .
H35A H 0.5625 0.9687 0.2643 0.067 Uiso 1 1 calc R U . . .
H35B H 0.5768 0.8790 0.1901 0.067 Uiso 1 1 calc R U . . .
H35C H 0.6738 0.8990 0.3161 0.067 Uiso 1 1 calc R U . . .
C36 C 0.5065(3) 0.9039(2) 0.4637(3) 0.0342(7) Uani 1 1 d . . . . .
H36A H 0.5915 0.8941 0.5142 0.051 Uiso 1 1 calc R U . . .
H36B H 0.4418 0.8796 0.5052 0.051 Uiso 1 1 calc R U . . .
H36C H 0.4922 0.9682 0.4502 0.051 Uiso 1 1 calc R U . . .
C37 C 0.5148(2) 0.5844(2) 0.2612(2) 0.0239(6) Uani 1 1 d . . . . .
H37 H 0.4547 0.5705 0.3162 0.029 Uiso 1 1 calc R U . . .
C38 C 0.6511(3) 0.5647(2) 0.3328(3) 0.0324(7) Uani 1 1 d . . . . .
H38A H 0.6617 0.5931 0.4140 0.039 Uiso 1 1 calc R U . . .
H38B H 0.6597 0.4992 0.3457 0.039 Uiso 1 1 calc R U . . .
C39 C 0.7600(3) 0.5965(3) 0.2730(3) 0.0381(8) Uani 1 1 d . . . . .
H39A H 0.7737 0.5513 0.2124 0.046 Uiso 1 1 calc R U . . .
H39B H 0.8393 0.6001 0.3363 0.046 Uiso 1 1 calc R U . . .
C40 C 0.7363(2) 0.6878(2) 0.2094(3) 0.0298(7) Uani 1 1 d . . . . .
H40A H 0.7966 0.6944 0.1537 0.036 Uiso 1 1 calc R U . . .
H40B H 0.7566 0.7352 0.2721 0.036 Uiso 1 1 calc R U . . .
C41 C 0.5991(2) 0.7041(2) 0.1350(2) 0.0231(6) Uani 1 1 d . . . . .
H41 H 0.5931 0.7675 0.1056 0.028 Uiso 1 1 calc R U . . .
C42 C 0.5676(3) 0.6416(2) 0.0228(3) 0.0292(7) Uani 1 1 d . . . . .
H42A H 0.4873 0.6627 -0.0300 0.035 Uiso 1 1 calc R U . . .
H42B H 0.6359 0.6481 -0.0242 0.035 Uiso 1 1 calc R U . . .
C43 C 0.5530(3) 0.5425(2) 0.0484(3) 0.0365(8) Uani 1 1 d . . . . .
H43A H 0.6386 0.5155 0.0748 0.044 Uiso 1 1 calc R U . . .
H43B H 0.5104 0.5123 -0.0277 0.044 Uiso 1 1 calc R U . . .
C44 C 0.4757(3) 0.5265(2) 0.1463(3) 0.0335(7) Uani 1 1 d . . . . .
H44A H 0.4839 0.4627 0.1706 0.040 Uiso 1 1 calc R U . . .
H44B H 0.3847 0.5380 0.1107 0.040 Uiso 1 1 calc R U . . .
N1 N 0.10056(19) 0.73237(15) -0.10550(19) 0.0196(5) Uani 1 1 d . . . . .
N2 N 0.34389(19) 0.71172(15) 0.18002(18) 0.0189(5) Uani 1 1 d . . . . .
B1 B -0.0353(3) 0.6800(2) -0.1832(3) 0.0199(6) Uani 1 1 d . . . . .
B2 B 0.5044(3) 0.6920(2) 0.2318(3) 0.0204(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(3) . ?
C1 C2 1.414(3) . ?
C1 C9 1.483(3) . ?
C2 C3 1.357(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(4) . ?
C3 H3 0.9500 . ?
C4 N2 1.388(3) . ?
C4 C8 1.407(3) . ?
C5 N2 1.342(3) . ?
C5 C6 1.414(3) . ?
C5 C27 1.479(3) . ?
C6 C7 1.359(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.385(3) . ?
C9 C10 1.394(4) . ?
C9 C14 1.407(3) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.504(4) . ?
C15 C16 1.561(4) . ?
C15 B1 1.646(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.526(4) . ?
C16 C18 1.528(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C26 1.540(4) . ?
C19 C20 1.549(4) . ?
C19 B1 1.638(4) . ?
C19 H19 1.0000 . ?
C20 C21 1.536(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.527(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.549(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.546(4) . ?
C23 B1 1.639(4) . ?
C23 H23 1.0000 . ?
C24 C25 1.528(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.523(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.399(4) . ?
C27 C32 1.404(4) . ?
C28 C29 1.377(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.512(4) . ?
C33 C34 1.552(4) . ?
C33 B2 1.648(4) . ?
C33 H33 1.0000 . ?
C34 C35 1.523(4) . ?
C34 C36 1.535(4) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C44 1.536(4) . ?
C37 C38 1.543(4) . ?
C37 B2 1.641(4) . ?
C37 H37 1.0000 . ?
C38 C39 1.535(4) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.536(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.554(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.547(4) . ?
C41 B2 1.641(4) . ?
C41 H41 1.0000 . ?
C42 C43 1.522(5) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.523(4) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
N1 B1 1.723(4) . ?
N2 B2 1.724(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 120.0(2) . . ?
N1 C1 C9 120.5(2) . . ?
C2 C1 C9 119.5(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
N2 C4 C3 121.1(2) . . ?
N2 C4 C8 121.5(2) . . ?
C3 C4 C8 116.9(2) . . ?
N2 C5 C6 120.2(2) . . ?
N2 C5 C27 120.2(2) . . ?
C6 C5 C27 119.6(2) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N1 C8 C7 121.0(2) . . ?
N1 C8 C4 121.6(2) . . ?
C7 C8 C4 117.1(2) . . ?
C10 C9 C14 120.2(2) . . ?
C10 C9 C1 120.2(2) . . ?
C14 C9 C1 119.6(2) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 117.6(2) . . ?
C13 C14 C15 122.4(2) . . ?
C9 C14 C15 119.9(2) . . ?
C14 C15 C16 111.6(2) . . ?
C14 C15 B1 105.8(2) . . ?
C16 C15 B1 117.3(2) . . ?
C14 C15 H15 107.2 . . ?
C16 C15 H15 107.2 . . ?
B1 C15 H15 107.2 . . ?
C17 C16 C18 108.8(2) . . ?
C17 C16 C15 111.0(2) . . ?
C18 C16 C15 113.4(2) . . ?
C17 C16 H16 107.8 . . ?
C18 C16 H16 107.8 . . ?
C15 C16 H16 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C19 C20 113.9(2) . . ?
C26 C19 B1 112.3(2) . . ?
C20 C19 B1 107.9(2) . . ?
C26 C19 H19 107.5 . . ?
C20 C19 H19 107.5 . . ?
B1 C19 H19 107.5 . . ?
C21 C20 C19 115.0(2) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C20 114.8(2) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 115.4(2) . . ?
C21 C22 H22A 108.4 . . ?
C23 C22 H22A 108.4 . . ?
C21 C22 H22B 108.4 . . ?
C23 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C24 C23 C22 110.4(2) . . ?
C24 C23 B1 115.4(2) . . ?
C22 C23 B1 105.8(2) . . ?
C24 C23 H23 108.3 . . ?
C22 C23 H23 108.3 . . ?
B1 C23 H23 108.3 . . ?
C25 C24 C23 116.0(2) . . ?
C25 C24 H24A 108.3 . . ?
C23 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
C23 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C26 C25 C24 113.1(3) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C19 114.4(2) . . ?
C25 C26 H26A 108.7 . . ?
C19 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C19 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C32 119.8(2) . . ?
C28 C27 C5 120.1(2) . . ?
C32 C27 C5 120.1(2) . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 121.7(3) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C31 C32 C27 118.1(2) . . ?
C31 C32 C33 122.3(2) . . ?
C27 C32 C33 119.6(2) . . ?
C32 C33 C34 110.8(2) . . ?
C32 C33 B2 105.4(2) . . ?
C34 C33 B2 118.7(2) . . ?
C32 C33 H33 107.1 . . ?
C34 C33 H33 107.1 . . ?
B2 C33 H33 107.1 . . ?
C35 C34 C36 107.6(2) . . ?
C35 C34 C33 112.3(2) . . ?
C36 C34 C33 112.5(2) . . ?
C35 C34 H34 108.1 . . ?
C36 C34 H34 108.1 . . ?
C33 C34 H34 108.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C44 C37 C38 113.3(2) . . ?
C44 C37 B2 112.8(2) . . ?
C38 C37 B2 108.0(2) . . ?
C44 C37 H37 107.5 . . ?
C38 C37 H37 107.5 . . ?
B2 C37 H37 107.5 . . ?
C39 C38 C37 115.9(2) . . ?
C39 C38 H38A 108.3 . . ?
C37 C38 H38A 108.3 . . ?
C39 C38 H38B 108.3 . . ?
C37 C38 H38B 108.3 . . ?
H38A C38 H38B 107.4 . . ?
C38 C39 C40 114.2(2) . . ?
C38 C39 H39A 108.7 . . ?
C40 C39 H39A 108.7 . . ?
C38 C39 H39B 108.7 . . ?
C40 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
C39 C40 C41 115.9(2) . . ?
C39 C40 H40A 108.3 . . ?
C41 C40 H40A 108.3 . . ?
C39 C40 H40B 108.3 . . ?
C41 C40 H40B 108.3 . . ?
H40A C40 H40B 107.4 . . ?
C42 C41 C40 111.5(2) . . ?
C42 C41 B2 114.2(2) . . ?
C40 C41 B2 105.9(2) . . ?
C42 C41 H41 108.4 . . ?
C40 C41 H41 108.4 . . ?
B2 C41 H41 108.4 . . ?
C43 C42 C41 116.6(3) . . ?
C43 C42 H42A 108.1 . . ?
C41 C42 H42A 108.1 . . ?
C43 C42 H42B 108.1 . . ?
C41 C42 H42B 108.1 . . ?
H42A C42 H42B 107.3 . . ?
C42 C43 C44 112.4(3) . . ?
C42 C43 H43A 109.1 . . ?
C44 C43 H43A 109.1 . . ?
C42 C43 H43B 109.1 . . ?
C44 C43 H43B 109.1 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 C37 114.9(2) . . ?
C43 C44 H44A 108.6 . . ?
C37 C44 H44A 108.6 . . ?
C43 C44 H44B 108.6 . . ?
C37 C44 H44B 108.6 . . ?
H44A C44 H44B 107.5 . . ?
C1 N1 C8 118.3(2) . . ?
C1 N1 B1 115.7(2) . . ?
C8 N1 B1 125.6(2) . . ?
C5 N2 C4 118.3(2) . . ?
C5 N2 B2 115.43(19) . . ?
C4 N2 B2 126.1(2) . . ?
C19 B1 C23 102.6(2) . . ?
C19 B1 C15 113.3(2) . . ?
C23 B1 C15 118.6(2) . . ?
C19 B1 N1 104.11(19) . . ?
C23 B1 N1 119.0(2) . . ?
C15 B1 N1 98.9(2) . . ?
C37 B2 C41 102.4(2) . . ?
C37 B2 C33 113.6(2) . . ?
C41 B2 C33 119.0(2) . . ?
C37 B2 N2 104.9(2) . . ?
C41 B2 N2 117.9(2) . . ?
C33 B2 N2 98.72(19) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1576565'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2017-11-27 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            'C50 H29 B2 F20 N3'
_chemical_formula_weight         1073.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   13.3636(3)
_cell_length_b                   12.7650(2)
_cell_length_c                   15.0491(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.844(2)
_cell_angle_gamma                90
_cell_volume                     2382.85(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4783
_cell_measurement_theta_min      3.4470
_cell_measurement_theta_max      74.0410

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    1.265
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_reflns_number            9545
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.462
_diffrn_reflns_theta_max         74.117
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4709
_reflns_number_gt                4051
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1192P)²+0.7405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4709
_refine_ls_number_parameters     356
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1688
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45569(16) 0.08371(15) 0.66992(13) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.35799(16) 0.03209(17) 0.65083(15) 0.0263(4) Uani 1 1 d . . . . .
H2 H 0.2924 0.0678 0.6169 0.032 Uiso 1 1 calc R U . . .
C3 C 0.35449(17) -0.07111(18) 0.68053(15) 0.0287(5) Uani 1 1 d . . . . .
H3 H 0.2869 -0.1047 0.6666 0.034 Uiso 1 1 calc R U . . .
C4 C 0.44947(17) -0.12502(16) 0.73042(15) 0.0259(4) Uani 1 1 d . . . . .
H4 H 0.4468 -0.1947 0.7516 0.031 Uiso 1 1 calc R U . . .
C5 C 0.54762(16) -0.07639(15) 0.74889(14) 0.0230(4) Uani 1 1 d . . . . .
H5 H 0.6127 -0.1133 0.7817 0.028 Uiso 1 1 calc R U . . .
C6 C 0.55144(15) 0.02702(15) 0.71949(13) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.46109(15) 0.19773(15) 0.64425(13) 0.0207(4) Uani 1 1 d . . . . .
H7 H 0.3907 0.2298 0.6387 0.025 Uiso 1 1 calc R U . . .
C8 C 0.47046(17) 0.21134(16) 0.54374(14) 0.0248(4) Uani 1 1 d . . . . .
H8 H 0.4834 0.2875 0.5364 0.030 Uiso 1 1 calc R U . . .
C9 C 0.36326(18) 0.1833(2) 0.46434(15) 0.0345(5) Uani 1 1 d . . . . .
H9A H 0.3670 0.1992 0.4019 0.052 Uiso 1 1 calc R U . . .
H9B H 0.3052 0.2242 0.4724 0.052 Uiso 1 1 calc R U . . .
H9C H 0.3488 0.1084 0.4677 0.052 Uiso 1 1 calc R U . . .
C10 C 0.56059(17) 0.15106(19) 0.52673(15) 0.0311(5) Uani 1 1 d . . . . .
H10A H 0.5570 0.0770 0.5424 0.047 Uiso 1 1 calc R U . . .
H10B H 0.6306 0.1800 0.5675 0.047 Uiso 1 1 calc R U . . .
H10C H 0.5520 0.1576 0.4594 0.047 Uiso 1 1 calc R U . . .
C11 C 0.52187(15) 0.22429(16) 0.83331(14) 0.0223(4) Uani 1 1 d . . . . .
C12 C 0.57459(16) 0.16044(16) 0.91101(15) 0.0251(4) Uani 1 1 d . . . . .
C13 C 0.53780(18) 0.1398(2) 0.98420(15) 0.0322(5) Uani 1 1 d . . . . .
C14 C 0.44480(19) 0.1866(2) 0.98286(16) 0.0393(6) Uani 1 1 d . . . . .
C15 C 0.39094(17) 0.2546(2) 0.90940(16) 0.0345(5) Uani 1 1 d . . . . .
C16 C 0.42930(16) 0.27177(17) 0.83737(14) 0.0264(4) Uani 1 1 d . . . . .
C17 C 0.57748(16) 0.37589(15) 0.74290(14) 0.0220(4) Uani 1 1 d . . . . .
C18 C 0.65947(17) 0.41846(16) 0.82236(15) 0.0252(4) Uani 1 1 d . . . . .
C19 C 0.68449(19) 0.52390(17) 0.83599(17) 0.0323(5) Uani 1 1 d . . . . .
C20 C 0.6231(2) 0.59390(17) 0.76757(19) 0.0355(5) Uani 1 1 d . . . . .
C21 C 0.53832(19) 0.55780(18) 0.68945(17) 0.0326(5) Uani 1 1 d . . . . .
C22 C 0.51640(17) 0.45115(17) 0.67857(15) 0.0263(4) Uani 1 1 d . . . . .
C23 C 0.65574(15) 0.07773(15) 0.73918(13) 0.0196(4) Uani 1 1 d . . . . .
C24 C 0.7500 0.2323(2) 0.7500 0.0187(5) Uani 1 2 d S T P . .
H24 H 0.7500 0.3067 0.7500 0.022 Uiso 1 2 calc R U P . .
C25 C 0.7500 0.0241(2) 0.7500 0.0212(5) Uani 1 2 d S T P . .
H25 H 0.7500 -0.0504 0.7500 0.025 Uiso 1 2 calc R U P . .
N1 N 0.66044(12) 0.18508(12) 0.74621(11) 0.0187(3) Uani 1 1 d . . . . .
F12 F 0.66880(10) 0.11256(11) 0.92052(9) 0.0301(3) Uani 1 1 d . . . . .
F13 F 0.59212(12) 0.07456(14) 1.05586(10) 0.0445(4) Uani 1 1 d . . . . .
F14 F 0.40735(13) 0.16798(19) 1.05232(11) 0.0620(6) Uani 1 1 d . . . . .
F15 F 0.30209(11) 0.30391(16) 0.90964(11) 0.0493(4) Uani 1 1 d . . . . .
F16 F 0.37242(10) 0.33875(11) 0.76767(9) 0.0328(3) Uani 1 1 d . . . . .
F18 F 0.72232(10) 0.35349(10) 0.89203(9) 0.0298(3) Uani 1 1 d . . . . .
F19 F 0.76635(12) 0.55757(12) 0.91282(11) 0.0444(4) Uani 1 1 d . . . . .
F20 F 0.64525(14) 0.69654(11) 0.77848(13) 0.0512(4) Uani 1 1 d . . . . .
F21 F 0.47626(14) 0.62593(11) 0.62455(12) 0.0476(4) Uani 1 1 d . . . . .
F22 F 0.42884(11) 0.42430(10) 0.60268(9) 0.0346(3) Uani 1 1 d . . . . .
B1 B 0.55252(17) 0.24976(17) 0.73871(15) 0.0196(4) Uani 1 1 d . . . . .
C26 C 0.2861(8) 0.5664(9) 0.8993(7) 0.094(3) Uani 0.5 1 d D U P . .
H26A H 0.3026 0.5051 0.9416 0.141 Uiso 0.5 1 calc R U P . .
H26B H 0.2265 0.5497 0.8393 0.141 Uiso 0.5 1 calc R U P . .
H26C H 0.2655 0.6252 0.9308 0.141 Uiso 0.5 1 calc R U P . .
C27 C 0.3748(8) 0.5931(6) 0.8803(6) 0.085(3) Uani 0.5 1 d D U P . .
N2 N 0.4436(10) 0.6188(9) 0.8599(10) 0.150(5) Uani 0.5 1 d D U 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
C1 C2 1.394(3) . ?
C1 C6 1.417(3) . ?
C1 C7 1.514(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C23 1.464(3) . ?
C7 C8 1.573(3) . ?
C7 B1 1.632(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.528(3) . ?
C8 C10 1.529(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.384(3) . ?
C11 C16 1.399(3) . ?
C11 B1 1.653(3) . ?
C12 F12 1.358(2) . ?
C12 C13 1.388(3) . ?
C13 F13 1.342(3) . ?
C13 C14 1.373(3) . ?
C14 F14 1.338(3) . ?
C14 C15 1.379(3) . ?
C15 F15 1.345(3) . ?
C15 C16 1.378(3) . ?
C16 F16 1.348(2) . ?
C17 C22 1.392(3) . ?
C17 C18 1.397(3) . ?
C17 B1 1.641(3) . ?
C18 F18 1.355(2) . ?
C18 C19 1.384(3) . ?
C19 F19 1.333(3) . ?
C19 C20 1.379(3) . ?
C20 F20 1.340(3) . ?
C20 C21 1.374(3) . ?
C21 F21 1.340(3) . ?
C21 C22 1.389(3) . ?
C22 F22 1.340(2) . ?
C23 N1 1.374(2) . ?
C23 C25 1.389(2) . ?
C24 N1 1.322(2) . ?
C24 N1 1.322(2) 2_656 ?
C24 H24 0.9500 . ?
C25 C23 1.389(2) 2_656 ?
C25 H25 0.9500 . ?
N1 B1 1.629(2) . ?
C26 C27 1.362(10) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 N2 1.121(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.41(18) . . ?
C2 C1 C7 122.12(18) . . ?
C6 C1 C7 120.39(17) . . ?
C1 C2 C3 121.34(19) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.40(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.52(19) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.23(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.09(18) . . ?
C5 C6 C23 119.82(17) . . ?
C1 C6 C23 119.09(17) . . ?
C1 C7 C8 112.32(16) . . ?
C1 C7 B1 105.09(15) . . ?
C8 C7 B1 119.40(16) . . ?
C1 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
B1 C7 H7 106.4 . . ?
C9 C8 C10 108.59(17) . . ?
C9 C8 C7 109.82(17) . . ?
C10 C8 C7 117.05(17) . . ?
C9 C8 H8 107.0 . . ?
C10 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 113.50(18) . . ?
C12 C11 B1 129.19(17) . . ?
C16 C11 B1 117.30(17) . . ?
F12 C12 C11 120.98(17) . . ?
F12 C12 C13 114.76(18) . . ?
C11 C12 C13 124.3(2) . . ?
F13 C13 C14 119.9(2) . . ?
F13 C13 C12 120.7(2) . . ?
C14 C13 C12 119.4(2) . . ?
F14 C14 C13 120.7(2) . . ?
F14 C14 C15 120.2(2) . . ?
C13 C14 C15 119.1(2) . . ?
F15 C15 C16 121.0(2) . . ?
F15 C15 C14 119.4(2) . . ?
C16 C15 C14 119.6(2) . . ?
F16 C16 C15 116.47(19) . . ?
F16 C16 C11 119.52(18) . . ?
C15 C16 C11 124.0(2) . . ?
C22 C17 C18 113.40(18) . . ?
C22 C17 B1 126.31(18) . . ?
C18 C17 B1 119.88(17) . . ?
F18 C18 C19 115.76(19) . . ?
F18 C18 C17 119.15(18) . . ?
C19 C18 C17 125.1(2) . . ?
F19 C19 C20 120.4(2) . . ?
F19 C19 C18 121.1(2) . . ?
C20 C19 C18 118.4(2) . . ?
F20 C20 C21 120.5(2) . . ?
F20 C20 C19 119.9(2) . . ?
C21 C20 C19 119.6(2) . . ?
F21 C21 C20 119.7(2) . . ?
F21 C21 C22 120.3(2) . . ?
C20 C21 C22 120.0(2) . . ?
F22 C22 C21 115.46(19) . . ?
F22 C22 C17 121.07(19) . . ?
C21 C22 C17 123.4(2) . . ?
N1 C23 C25 117.99(17) . . ?
N1 C23 C6 118.00(16) . . ?
C25 C23 C6 124.00(18) . . ?
N1 C24 N1 125.8(2) . 2_656 ?
N1 C24 H24 117.1 . . ?
N1 C24 H24 117.1 2_656 . ?
C23 C25 C23 120.9(2) . 2_656 ?
C23 C25 H25 119.5 . . ?
C23 C25 H25 119.5 2_656 . ?
C24 N1 C23 118.20(17) . . ?
C24 N1 B1 122.40(17) . . ?
C23 N1 B1 119.10(15) . . ?
N1 B1 C7 102.17(14) . . ?
N1 B1 C17 109.43(15) . . ?
C7 B1 C17 120.57(16) . . ?
N1 B1 C11 109.71(15) . . ?
C7 B1 C11 108.96(15) . . ?
C17 B1 C11 105.78(15) . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 C26 175.5(15) . . ?

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1576566'
_audit_update_record             
;
2017-09-26 deposited with the CCDC.
2017-11-27 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            'C60 H38 B2 F20 N2'
_chemical_formula_weight         1188.54

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'
F F 0.0171 0.0103 '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'

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

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

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

_cell_length_a                   11.196(5)
_cell_length_b                   13.488(7)
_cell_length_c                   19.102(11)
_cell_angle_alpha                102.11(2)
_cell_angle_beta                 104.06(2)
_cell_angle_gamma                108.18(2)
_cell_volume                     2528(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.33

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             1204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7206
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0686 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.9667. The λ/2 correction factor is Not present.'
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83239
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         28.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             10291
_reflns_number_gt                8956
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+1.5049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10291
_refine_ls_number_parameters     761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.65770(15) 0.57370(13) 0.85289(9) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.67832(16) 0.49565(14) 0.88187(9) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.6489 0.4835 0.9231 0.025 Uiso 1 1 calc R U . . .
C3 C 0.74533(17) 0.42918(14) 0.85079(10) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.7584 0.3758 0.8740 0.028 Uiso 1 1 calc R U . . .
C4 C 0.79313(17) 0.43761(14) 0.78822(10) 0.0232(4) Uani 1 1 d . . . . .
H4 H 0.8350 0.3915 0.7697 0.028 Uiso 1 1 calc R U . . .
C5 C 0.77508(16) 0.51383(14) 0.75800(9) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.8042 0.5242 0.7164 0.025 Uiso 1 1 calc R U . . .
C6 C 0.70892(15) 0.58268(13) 0.78999(9) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.58287(15) 0.64542(13) 0.88643(9) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.5208 0.5969 0.9061 0.021 Uiso 1 1 calc R U . . .
C8 C 0.67113(16) 0.75380(14) 0.95610(9) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.6160 0.7988 0.9618 0.026 Uiso 1 1 calc R U . . .
C9 C 0.79649(17) 0.82361(15) 0.94245(10) 0.0275(4) Uani 1 1 d . . . . .
H9A H 0.8491 0.8888 0.9868 0.041 Uiso 1 1 calc R U . . .
H9B H 0.7697 0.8463 0.8976 0.041 Uiso 1 1 calc R U . . .
H9C H 0.8503 0.7801 0.9343 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7055(2) 0.72498(17) 1.02592(10) 0.0321(4) Uani 1 1 d . . . . .
H10A H 0.7628 0.6834 1.0227 0.048 Uiso 1 1 calc R U . . .
H10B H 0.6239 0.6801 1.0325 0.048 Uiso 1 1 calc R U . . .
H10C H 0.7528 0.7921 1.0693 0.048 Uiso 1 1 calc R U . . .
C11 C 0.40338(15) 0.52675(13) 0.75148(9) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.35806(16) 0.51123(13) 0.67624(9) 0.0194(3) Uani 1 1 d . . . . .
C13 C 0.28441(16) 0.40950(14) 0.61880(9) 0.0224(4) Uani 1 1 d . . . . .
C14 C 0.24913(16) 0.31357(14) 0.63507(10) 0.0236(4) Uani 1 1 d . . . . .
C15 C 0.28781(16) 0.32318(14) 0.70899(10) 0.0230(4) Uani 1 1 d . . . . .
C16 C 0.36130(15) 0.42687(14) 0.76476(9) 0.0201(3) Uani 1 1 d . . . . .
C17 C 0.40705(15) 0.73298(13) 0.83866(8) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.45855(15) 0.84924(14) 0.87620(9) 0.0185(3) Uani 1 1 d . . . . .
C19 C 0.38707(17) 0.91607(14) 0.89750(9) 0.0218(4) Uani 1 1 d . . . . .
C20 C 0.25384(17) 0.86703(16) 0.88026(10) 0.0250(4) Uani 1 1 d . . . . .
C21 C 0.19640(16) 0.75263(15) 0.84248(10) 0.0234(4) Uani 1 1 d . . . . .
C22 C 0.27155(16) 0.68871(14) 0.82387(9) 0.0191(3) Uani 1 1 d . . . . .
C23 C 0.69547(15) 0.66559(13) 0.75841(9) 0.0164(3) Uani 1 1 d . . . . .
C24 C 0.77949(15) 0.70833(13) 0.71776(9) 0.0174(3) Uani 1 1 d . . . . .
H24 H 0.8439 0.6792 0.7098 0.021 Uiso 1 1 calc R U . . .
C25 C 0.76713(15) 0.78964(13) 0.69085(8) 0.0163(3) Uani 1 1 d . . . . .
C26 C 0.59119(15) 0.78501(13) 0.74394(8) 0.0151(3) Uani 1 1 d . . . . .
H26 H 0.5269 0.8143 0.7518 0.018 Uiso 1 1 calc R U . . .
C27 C 0.85827(15) 0.84099(14) 0.65168(9) 0.0182(3) Uani 1 1 d . . . . .
C28 C 0.92240(16) 0.77949(15) 0.60965(9) 0.0222(4) Uani 1 1 d . . . . .
H28 H 0.9034 0.7049 0.6072 0.027 Uiso 1 1 calc R U . . .
C29 C 1.01002(17) 0.82760(16) 0.57339(10) 0.0258(4) Uani 1 1 d . . . . .
H29 H 1.0491 0.7874 0.5458 0.031 Uiso 1 1 calc R U . . .
C30 C 1.03600(17) 0.93835(16) 0.58051(10) 0.0278(4) Uani 1 1 d . . . . .
H30 H 1.0956 0.9750 0.5578 0.033 Uiso 1 1 calc R U . . .
C31 C 0.97265(16) 0.99998(15) 0.62266(10) 0.0238(4) Uani 1 1 d . . . . .
H31 H 0.9943 1.0751 0.6259 0.029 Uiso 1 1 calc R U . . .
C32 C 0.88171(15) 0.95318(14) 0.65833(9) 0.0189(3) Uani 1 1 d . . . . .
C33 C 0.80603(15) 1.01542(13) 0.70123(9) 0.0180(3) Uani 1 1 d . . . . .
H33 H 0.7997 1.0733 0.6770 0.022 Uiso 1 1 calc R U . . .
C34 C 0.87264(16) 1.07729(13) 0.78876(9) 0.0199(3) Uani 1 1 d . . . . .
H34 H 0.8016 1.0830 0.8106 0.024 Uiso 1 1 calc R U . . .
C35 C 0.93919(18) 1.01581(15) 0.82538(10) 0.0278(4) Uani 1 1 d . . . . .
H35A H 1.0036 1.0040 0.8012 0.042 Uiso 1 1 calc R U . . .
H35B H 0.8730 0.9447 0.8203 0.042 Uiso 1 1 calc R U . . .
H35C H 0.9859 1.0572 0.8793 0.042 Uiso 1 1 calc R U . . .
C36 C 0.97234(19) 1.19325(15) 0.80317(11) 0.0325(4) Uani 1 1 d . . . . .
H36A H 1.0140 1.2302 0.8580 0.049 Uiso 1 1 calc R U . . .
H36B H 0.9256 1.2349 0.7801 0.049 Uiso 1 1 calc R U . . .
H36C H 1.0411 1.1887 0.7807 0.049 Uiso 1 1 calc R U . . .
C37 C 0.60897(15) 0.86839(13) 0.58015(9) 0.0174(3) Uani 1 1 d . . . . .
C38 C 0.61904(16) 0.93806(14) 0.53862(10) 0.0213(4) Uani 1 1 d . . . . .
C39 C 0.58348(17) 0.89989(16) 0.46023(10) 0.0259(4) Uani 1 1 d . . . . .
C40 C 0.52901(17) 0.78638(16) 0.41846(9) 0.0262(4) Uani 1 1 d . . . . .
C41 C 0.51512(16) 0.71276(15) 0.45616(10) 0.0229(4) Uani 1 1 d . . . . .
C42 C 0.55634(16) 0.75479(14) 0.53465(9) 0.0199(3) Uani 1 1 d . . . . .
C43 C 0.54529(15) 0.97138(13) 0.70560(9) 0.0174(3) Uani 1 1 d . . . . .
C44 C 0.56244(16) 1.08218(14) 0.74636(9) 0.0198(3) Uani 1 1 d . . . . .
C45 C 0.46643(17) 1.11568(14) 0.77369(9) 0.0222(4) Uani 1 1 d . . . . .
C46 C 0.34441(17) 1.03621(15) 0.76019(10) 0.0238(4) Uani 1 1 d . . . . .
C47 C 0.31991(16) 0.92580(14) 0.71707(9) 0.0223(4) Uani 1 1 d . . . . .
C48 C 0.41734(16) 0.89713(13) 0.68920(9) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.59942(12) 0.70690(11) 0.77121(7) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.66844(12) 0.82764(10) 0.70494(7) 0.0148(3) Uani 1 1 d . . . . .
F12 F 0.38200(10) 0.60175(8) 0.65596(6) 0.0295(2) Uani 1 1 d . . . . .
F13 F 0.24683(11) 0.40406(9) 0.54783(6) 0.0365(3) Uani 1 1 d . . . . .
F14 F 0.17794(11) 0.21307(9) 0.58099(6) 0.0352(3) Uani 1 1 d . . . . .
F15 F 0.25300(10) 0.23009(8) 0.72576(7) 0.0347(3) Uani 1 1 d . . . . .
F16 F 0.38700(10) 0.42562(8) 0.83547(6) 0.0295(2) Uani 1 1 d . . . . .
F18 F 0.58843(9) 0.90644(8) 0.89194(5) 0.0233(2) Uani 1 1 d . . . . .
F19 F 0.44543(11) 1.02782(8) 0.93336(6) 0.0307(2) Uani 1 1 d . . . . .
F20 F 0.18275(11) 0.92987(10) 0.89962(7) 0.0376(3) Uani 1 1 d . . . . .
F21 F 0.06652(10) 0.70350(10) 0.82297(7) 0.0347(3) Uani 1 1 d . . . . .
F22 F 0.20439(9) 0.57747(8) 0.78940(6) 0.0261(2) Uani 1 1 d . . . . .
F38 F 0.66502(10) 1.05089(8) 0.57514(6) 0.0292(2) Uani 1 1 d . . . . .
F39 F 0.60123(11) 0.97379(10) 0.42488(6) 0.0367(3) Uani 1 1 d . . . . .
F40 F 0.48954(12) 0.74797(11) 0.34263(6) 0.0380(3) Uani 1 1 d . . . . .
F41 F 0.46078(11) 0.60161(9) 0.41679(6) 0.0320(2) Uani 1 1 d . . . . .
F42 F 0.54014(10) 0.67572(8) 0.56600(5) 0.0259(2) Uani 1 1 d . . . . .
F44 F 0.67652(9) 1.16635(8) 0.76048(6) 0.0261(2) Uani 1 1 d . . . . .
F45 F 0.49077(11) 1.22372(9) 0.81344(6) 0.0314(2) Uani 1 1 d . . . . .
F46 F 0.25202(11) 1.06594(10) 0.78862(7) 0.0337(3) Uani 1 1 d . . . . .
F47 F 0.20276(9) 0.84649(9) 0.70382(6) 0.0317(3) Uani 1 1 d . . . . .
F48 F 0.38480(9) 0.78802(8) 0.64493(5) 0.0239(2) Uani 1 1 d . . . . .
B1 B 0.49437(17) 0.65416(15) 0.81587(10) 0.0151(3) Uani 1 1 d . . . . .
B2 B 0.65647(17) 0.92629(15) 0.67406(10) 0.0161(4) Uani 1 1 d . . . . .
C49 C -0.12645(19) 0.29626(17) 0.60730(11) 0.0312(4) Uani 1 1 d . . . . .
H49 H -0.1350 0.2351 0.6258 0.037 Uiso 1 1 calc R U . . .
C50 C -0.02092(19) 0.39481(17) 0.64597(11) 0.0333(4) Uani 1 1 d . . . . .
H50 H 0.0418 0.3996 0.6914 0.040 Uiso 1 1 calc R U . . .
C51 C -0.00112(19) 0.48513(17) 0.62315(12) 0.0342(4) Uani 1 1 d . . . . .
H51 H 0.0735 0.5517 0.6510 0.041 Uiso 1 1 calc R U . . .
C52 C -0.0889(2) 0.47646(17) 0.56134(11) 0.0338(4) Uani 1 1 d . . . . .
H52 H -0.0801 0.5375 0.5428 0.041 Uiso 1 1 calc R U . . .
C53 C -0.1951(2) 0.37814(17) 0.52285(11) 0.0345(4) Uani 1 1 d . . . . .
H53 H -0.2587 0.3737 0.4779 0.041 Uiso 1 1 calc R U . . .
C54 C -0.21400(18) 0.28757(17) 0.54546(11) 0.0318(4) Uani 1 1 d . . . . .
H54 H -0.2880 0.2207 0.5173 0.038 Uiso 1 1 calc R U . . .
C55 C 0.1363(2) 0.74721(19) 1.01571(12) 0.0401(5) Uani 1 1 d . . . . .
H55 H 0.0941 0.7952 1.0306 0.048 Uiso 1 1 calc R U . . .
C56 C 0.0619(2) 0.6373(2) 0.97145(13) 0.0464(6) Uani 1 1 d . . . . .
H56 H -0.0325 0.6117 0.9572 0.056 Uiso 1 1 calc R U . . .
C57 C 0.1196(3) 0.5616(2) 0.94647(13) 0.0471(6) Uani 1 1 d . . . . .
H57 H 0.0645 0.4880 0.9164 0.056 Uiso 1 1 calc R U . . .
C58 C 0.2538(3) 0.5963(2) 0.96633(13) 0.0463(6) Uani 1 1 d . . . . .
H58 H 0.2961 0.5488 0.9506 0.056 Uiso 1 1 calc R U . . .
C59 C 0.3280(2) 0.7068(2) 1.01161(12) 0.0436(6) Uani 1 1 d . . . . .
H59 H 0.4225 0.7329 1.0266 0.052 Uiso 1 1 calc R U . . .
C60 C 0.2691(2) 0.78176(19) 1.03619(12) 0.0412(5) Uani 1 1 d . . . . .
H60 H 0.3236 0.8553 1.0667 0.049 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
C1 C2 1.343(2) . ?
C1 C6 1.463(2) . ?
C1 C7 1.598(2) . ?
C2 C3 1.460(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.434(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.324(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.482(2) . ?
C5 H5 0.9500 . ?
C6 C23 1.408(2) . ?
C7 B1 1.518(2) . ?
C7 C8 1.590(2) . ?
C7 H7 1.0000 . ?
C8 C10 1.463(2) . ?
C8 C9 1.543(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.349(2) . ?
C11 C16 1.381(2) . ?
C11 B1 1.708(3) . ?
C12 F12 1.3257(19) . ?
C12 C13 1.410(3) . ?
C13 F13 1.297(2) . ?
C13 C14 1.355(2) . ?
C14 C15 1.338(3) . ?
C14 F14 1.370(2) . ?
C15 F15 1.3249(19) . ?
C15 C16 1.414(3) . ?
C16 F16 1.316(2) . ?
C17 C22 1.376(2) . ?
C17 C18 1.438(2) . ?
C17 B1 1.714(2) . ?
C18 F18 1.3380(19) . ?
C18 C19 1.440(2) . ?
C19 C20 1.351(3) . ?
C19 F19 1.380(2) . ?
C20 F20 1.386(2) . ?
C20 C21 1.415(3) . ?
C21 F21 1.313(2) . ?
C21 C22 1.431(3) . ?
C22 F22 1.375(2) . ?
C23 N1 1.404(2) . ?
C23 C24 1.423(2) . ?
C24 C25 1.335(2) . ?
C24 H24 0.9500 . ?
C25 N2 1.413(2) . ?
C25 C27 1.493(2) . ?
C26 N1 1.287(2) . ?
C26 N2 1.348(2) . ?
C26 H26 0.9500 . ?
C27 C32 1.425(2) . ?
C27 C28 1.490(3) . ?
C28 C29 1.409(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.400(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.485(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.420(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.608(2) . ?
C33 C34 1.571(2) . ?
C33 B2 1.606(2) . ?
C33 H33 1.0000 . ?
C34 C35 1.452(2) . ?
C34 C36 1.533(3) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.347(2) . ?
C37 C42 1.442(3) . ?
C37 B2 1.673(3) . ?
C38 C39 1.387(3) . ?
C38 F38 1.400(2) . ?
C39 F39 1.309(2) . ?
C39 C40 1.422(3) . ?
C40 C41 1.337(3) . ?
C40 F40 1.339(2) . ?
C41 F41 1.385(2) . ?
C41 C42 1.388(3) . ?
C42 F42 1.3149(19) . ?
C43 C48 1.381(2) . ?
C43 C44 1.462(3) . ?
C43 B2 1.722(3) . ?
C44 F44 1.339(2) . ?
C44 C45 1.452(3) . ?
C45 C46 1.371(3) . ?
C45 F45 1.401(2) . ?
C46 F46 1.402(2) . ?
C46 C47 1.446(3) . ?
C47 F47 1.333(2) . ?
C47 C48 1.443(3) . ?
C48 F48 1.417(2) . ?
N1 B1 1.684(2) . ?
N2 B2 1.593(2) . ?
C49 C54 1.295(3) . ?
C49 C50 1.376(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.351(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.296(3) . ?
C51 H51 0.9500 . ?
C52 C53 1.376(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.352(3) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 C60 1.337(3) . ?
C55 C56 1.402(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.431(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.353(4) . ?
C57 H57 0.9500 . ?
C58 C59 1.413(4) . ?
C58 H58 0.9500 . ?
C59 C60 1.430(4) . ?
C59 H59 0.9500 . ?
C60 H60 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
C2 C1 C6 113.08(15) . . ?
C2 C1 C7 120.72(15) . . ?
C6 C1 C7 126.20(13) . . ?
C1 C2 C3 120.84(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 125.51(14) . . ?
C4 C3 H3 117.2 . . ?
C2 C3 H3 117.2 . . ?
C5 C4 C3 115.65(16) . . ?
C5 C4 H4 122.2 . . ?
C3 C4 H4 122.2 . . ?
C4 C5 C6 119.12(16) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C23 C6 C1 116.44(15) . . ?
C23 C6 C5 117.77(15) . . ?
C1 C6 C5 125.79(14) . . ?
B1 C7 C8 118.75(14) . . ?
B1 C7 C1 103.06(13) . . ?
C8 C7 C1 117.50(13) . . ?
B1 C7 H7 105.4 . . ?
C8 C7 H7 105.4 . . ?
C1 C7 H7 105.4 . . ?
C10 C8 C9 111.62(15) . . ?
C10 C8 C7 109.76(15) . . ?
C9 C8 C7 111.82(14) . . ?
C10 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 109.31(15) . . ?
C12 C11 B1 122.16(14) . . ?
C16 C11 B1 128.51(14) . . ?
F12 C12 C11 115.60(15) . . ?
F12 C12 C13 118.05(14) . . ?
C11 C12 C13 126.30(15) . . ?
F13 C13 C14 117.10(16) . . ?
F13 C13 C12 121.11(15) . . ?
C14 C13 C12 121.79(16) . . ?
C15 C14 C13 115.09(16) . . ?
C15 C14 F14 121.29(16) . . ?
C13 C14 F14 123.62(16) . . ?
F15 C15 C14 115.75(16) . . ?
F15 C15 C16 122.98(16) . . ?
C14 C15 C16 121.28(15) . . ?
F16 C16 C11 118.54(15) . . ?
F16 C16 C15 115.25(14) . . ?
C11 C16 C15 126.18(15) . . ?
C22 C17 C18 110.01(15) . . ?
C22 C17 B1 122.22(15) . . ?
C18 C17 B1 127.75(14) . . ?
F18 C18 C17 117.99(14) . . ?
F18 C18 C19 113.56(15) . . ?
C17 C18 C19 128.40(15) . . ?
C20 C19 F19 117.52(16) . . ?
C20 C19 C18 118.23(16) . . ?
F19 C19 C18 124.24(15) . . ?
C19 C20 F20 119.26(17) . . ?
C19 C20 C21 116.29(16) . . ?
F20 C20 C21 124.45(16) . . ?
F21 C21 C20 117.55(16) . . ?
F21 C21 C22 118.72(16) . . ?
C20 C21 C22 123.73(15) . . ?
F22 C22 C17 118.62(15) . . ?
F22 C22 C21 118.06(14) . . ?
C17 C22 C21 123.32(16) . . ?
N1 C23 C6 117.20(14) . . ?
N1 C23 C24 121.64(14) . . ?
C6 C23 C24 121.11(15) . . ?
C25 C24 C23 119.52(15) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 N2 116.49(14) . . ?
C24 C25 C27 121.20(15) . . ?
N2 C25 C27 122.22(13) . . ?
N1 C26 N2 123.87(15) . . ?
N1 C26 H26 118.1 . . ?
N2 C26 H26 118.1 . . ?
C32 C27 C28 122.27(15) . . ?
C32 C27 C25 115.56(15) . . ?
C28 C27 C25 122.16(15) . . ?
C29 C28 C27 122.62(16) . . ?
C29 C28 H28 118.7 . . ?
C27 C28 H28 118.7 . . ?
C30 C29 C28 115.84(17) . . ?
C30 C29 H29 122.1 . . ?
C28 C29 H29 122.1 . . ?
C29 C30 C31 121.64(16) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 H30 119.2 . . ?
C32 C31 C30 123.84(16) . . ?
C32 C31 H31 118.1 . . ?
C30 C31 H31 118.1 . . ?
C31 C32 C27 113.76(16) . . ?
C31 C32 C33 125.39(15) . . ?
C27 C32 C33 120.84(14) . . ?
C34 C33 B2 116.30(14) . . ?
C34 C33 C32 118.91(13) . . ?
B2 C33 C32 104.11(13) . . ?
C34 C33 H33 105.4 . . ?
B2 C33 H33 105.4 . . ?
C32 C33 H33 105.4 . . ?
C35 C34 C36 110.22(15) . . ?
C35 C34 C33 109.76(15) . . ?
C36 C34 C33 110.50(14) . . ?
C35 C34 H34 108.8 . . ?
C36 C34 H34 108.8 . . ?
C33 C34 H34 108.8 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C42 113.15(15) . . ?
C38 C37 B2 115.85(15) . . ?
C42 C37 B2 131.00(13) . . ?
C37 C38 C39 121.19(17) . . ?
C37 C38 F38 119.42(15) . . ?
C39 C38 F38 119.39(14) . . ?
F39 C39 C38 116.91(17) . . ?
F39 C39 C40 120.19(16) . . ?
C38 C39 C40 122.90(15) . . ?
C41 C40 F40 117.37(18) . . ?
C41 C40 C39 118.93(16) . . ?
F40 C40 C39 123.70(16) . . ?
C40 C41 F41 120.10(16) . . ?
C40 C41 C42 116.16(17) . . ?
F41 C41 C42 123.74(15) . . ?
F42 C42 C41 111.15(16) . . ?
F42 C42 C37 121.23(15) . . ?
C41 C42 C37 127.61(15) . . ?
C48 C43 C44 111.52(15) . . ?
C48 C43 B2 118.89(15) . . ?
C44 C43 B2 129.53(14) . . ?
F44 C44 C45 113.01(15) . . ?
F44 C44 C43 119.53(15) . . ?
C45 C44 C43 127.45(15) . . ?
C46 C45 F45 117.92(16) . . ?
C46 C45 C44 117.85(16) . . ?
F45 C45 C44 124.23(15) . . ?
C45 C46 F46 118.83(17) . . ?
C45 C46 C47 117.01(16) . . ?
F46 C46 C47 124.16(15) . . ?
F47 C47 C48 118.53(16) . . ?
F47 C47 C46 118.39(16) . . ?
C48 C47 C46 123.06(15) . . ?
C43 C48 F48 117.14(15) . . ?
C43 C48 C47 122.80(16) . . ?
F48 C48 C47 120.02(14) . . ?
C26 N1 C23 116.42(14) . . ?
C26 N1 B1 120.96(13) . . ?
C23 N1 B1 122.55(12) . . ?
C26 N2 C25 122.05(13) . . ?
C26 N2 B2 121.83(13) . . ?
C25 N2 B2 116.10(13) . . ?
C7 B1 N1 104.66(13) . . ?
C7 B1 C11 109.98(13) . . ?
N1 B1 C11 99.98(12) . . ?
C7 B1 C17 111.34(14) . . ?
N1 B1 C17 113.26(12) . . ?
C11 B1 C17 116.51(13) . . ?
N2 B2 C33 105.52(12) . . ?
N2 B2 C37 101.86(13) . . ?
C33 B2 C37 107.74(13) . . ?
N2 B2 C43 109.40(12) . . ?
C33 B2 C43 115.66(14) . . ?
C37 B2 C43 115.34(12) . . ?
C54 C49 C50 119.38(19) . . ?
C54 C49 H49 120.3 . . ?
C50 C49 H49 120.3 . . ?
C51 C50 C49 123.90(18) . . ?
C51 C50 H50 118.0 . . ?
C49 C50 H50 118.0 . . ?
C52 C51 C50 116.69(19) . . ?
C52 C51 H51 121.7 . . ?
C50 C51 H51 121.7 . . ?
C51 C52 C53 119.49(19) . . ?
C51 C52 H52 120.3 . . ?
C53 C52 H52 120.3 . . ?
C54 C53 C52 123.68(18) . . ?
C54 C53 H53 118.2 . . ?
C52 C53 H53 118.2 . . ?
C49 C54 C53 116.85(19) . . ?
C49 C54 H54 121.6 . . ?
C53 C54 H54 121.6 . . ?
C60 C55 C56 117.4(2) . . ?
C60 C55 H55 121.3 . . ?
C56 C55 H55 121.3 . . ?
C55 C56 C57 123.9(2) . . ?
C55 C56 H56 118.0 . . ?
C57 C56 H56 118.0 . . ?
C58 C57 C56 119.0(2) . . ?
C58 C57 H57 120.5 . . ?
C56 C57 H57 120.5 . . ?
C57 C58 C59 116.7(2) . . ?
C57 C58 H58 121.7 . . ?
C59 C58 H58 121.7 . . ?
C58 C59 C60 123.7(2) . . ?
C58 C59 H59 118.1 . . ?
C60 C59 H59 118.1 . . ?
C55 C60 C59 119.3(2) . . ?
C55 C60 H60 120.4 . . ?
C59 C60 H60 120.4 . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.050



