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

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

data_10srv060
_database_code_depnum_ccdc_archive 'CCDC 1515550'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-21 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         'C4 H8 B2 O4'
_chemical_formula_sum            'C4 H8 B2 O4'
_chemical_formula_weight         141.72

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   3.9115(11)
_cell_length_b                   8.015(3)
_cell_length_c                   10.187(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.939(11)
_cell_angle_gamma                90
_cell_volume                     314.57(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1223
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      30.05

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2006/1 (Bruker AXS)'



_exptl_special_details           
;
 The collected data covered nominally more than a hemisphere of the
 reciprocal space. A combination of 4 sets of ω scans were used; each
 set at different φ angles and each scan 0.3 deg in ω. Each frame was
 exposed for 10s. Crystal to detector distance 4.85 cm. Corrected for
 crystal being wider than the beam, R(int)=0.0969 before correction.
;


_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1946
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             646
_reflns_number_gt                554
_reflns_threshold_expression     'I > 2σ(I)'


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;



_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'

_computing_structure_solution    
;
 SHELXS-97 (G. M. Sheldrick, Acta Cryst., 2008, A64, 112--122)
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_computing_molecular_graphics    
;

;
_computing_publication_material  
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;


_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Methyl groups were treated as rigid bodies and allowed to rotate about
 the E-CH3 bond but not to tip.


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



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.1228P] 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         646
_refine_ls_number_parameters     46
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.6023(4) 0.71943(18) 0.27330(13) 0.0211(4) Uani 1 1 d . . . . .
H1A H 0.3484 0.7373 0.2514 0.025 Uiso 1 1 calc R U . . .
H1B H 0.7020 0.7296 0.1907 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7704(4) 0.84454(18) 0.37838(14) 0.0218(4) Uani 1 1 d . . . . .
H2A H 0.9123 0.9267 0.3389 0.026 Uiso 1 1 calc R U . . .
H2B H 0.5915 0.9050 0.4176 0.026 Uiso 1 1 calc R U . . .
B1 B 0.9113(4) 0.57983(19) 0.45028(15) 0.0184(4) Uani 1 1 d . . . . .
O1 O 0.6811(3) 0.55705(12) 0.33501(10) 0.0239(3) Uani 1 1 d . . . . .
O2 O 0.9871(3) 0.74386(12) 0.47873(9) 0.0221(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4550(17) . ?
C1 C2 1.530(2) . ?
C2 O2 1.4547(17) . ?
B1 O1 1.3632(19) . ?
B1 O2 1.3677(19) . ?
B1 B1 1.704(3) 3_766 ?

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
O1 C1 C2 104.51(10) . . ?
O2 C2 C1 104.84(11) . . ?
O1 B1 O2 113.46(12) . . ?
O1 B1 B1 123.52(16) . 3_766 ?
O2 B1 B1 123.01(16) . 3_766 ?
B1 O1 C1 108.15(10) . . ?
B1 O2 C2 107.79(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 11.11(13) . . . . ?
O2 B1 O1 C1 3.28(16) . . . . ?
B1 B1 O1 C1 -176.67(15) 3_766 . . . ?
C2 C1 O1 B1 -8.92(14) . . . . ?
O1 B1 O2 C2 4.28(15) . . . . ?
B1 B1 O2 C2 -175.77(15) 3_766 . . . ?
C1 C2 O2 B1 -9.51(13) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_ck41ck_140K
_database_code_depnum_ccdc_archive 'CCDC 1515551'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-21 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         'C10 H20 B2 O4'
_chemical_formula_sum            'C10 H20 B2 O4'
_chemical_formula_weight         225.89

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

_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   8.8506(11)
_cell_length_b                   8.8506(11)
_cell_length_c                   13.7909(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     935.6(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    1851
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      26.84

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.34
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_crystal_recrystallization_method 
;
 Gas phase diffusion of n-hexane into a solution in C6H6 at rt.
;

_exptl_special_details           
;
 The crystal was mounted on top of a human hair with perfluorether oil
 and placed in the nitrogen gas stream on the diffractometer at 290 K.
 The temperature was lowered to 140 K in 25 K steps.
 At each temperature a full measuement was perfomed (approx. 5.5 h per step).

 A combination of 15 sets of ω scans were used; each set at different \j,
 2θ or κ angles and each scan 0.8 deg in ω.
 Each frame was exposed for 10s. Nominal crystal to detector distance 43 mm.
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_reflns_number            8208
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.041
_diffrn_reflns_theta_max         29.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             340
_reflns_number_gt                289
_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.
;



_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
;
 SHELXS (G. M. Sheldrick, Acta Cryst., 2008, A64, 112--122)
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. (2008), A64, 112-122)'
;
_computing_molecular_graphics    
;
 K. Brandenburg, 1999, Diamond 3.2i, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;


_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.


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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.6101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         340
_refine_ls_number_parameters     31
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.519(2) 0.7594(11) 0.4358(15) 0.072(5) Uani 0.3333 2 d S T P . .
H1A H 0.5710 0.8821 0.4167 0.107 Uiso 0.1667 1 calc R U P . .
H1B H 0.5320 0.7519 0.5059 0.107 Uiso 0.1667 1 calc R U P . .
H1C H 0.5776 0.7063 0.4015 0.107 Uiso 0.1667 1 calc R U P . .
C2 C 0.3333 0.6667 0.41074(14) 0.0304(5) Uani 1 6 d S T P . .
C3 C 0.3333 0.6667 0.30041(16) 0.0394(6) Uani 1 6 d S T P . .
H3A H 0.3936 0.7872 0.2767 0.059 Uiso 0.3333 2 calc R U P . .
H3B H 0.3936 0.6064 0.2767 0.059 Uiso 0.3333 2 calc R U P . .
H3C H 0.2128 0.6064 0.2767 0.059 Uiso 0.3333 2 calc R U P . .
C4 C 0.5185(7) 0.7592(3) 0.4529(6) 0.0472(12) Uani 0.6667 2 d S T P . .
H4A H 0.5827 0.7006 0.4309 0.057 Uiso 0.3333 1 calc R U P . .
H4B H 0.5827 0.8821 0.4309 0.057 Uiso 0.3333 1 calc R U P . .
B1 B 0.3695(3) 0.7390(6) 0.6050(3) 0.0548(15) Uani 0.3333 2 d S T P . .
O1 O 0.5045(2) 0.75224(12) 0.55775(12) 0.0648(7) Uani 0.6667 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.463(16) . ?
C2 C1 1.463(16) 3_565 ?
C2 C1 1.463(16) 2_665 ?
C2 C3 1.522(3) . ?
C2 C4 1.534(6) . ?
C2 C4 1.534(6) 2_665 ?
C2 C4 1.534(6) 3_565 ?
C4 O1 1.449(9) . ?
B1 B1 0.960(8) 2_665 ?
B1 B1 0.960(8) 3_565 ?
B1 O1 1.313(3) . ?
B1 O1 1.313(3) 2_665 ?
B1 B1 1.789(8) 26_456 ?
B1 B1 1.789(8) 27_556 ?
B1 O1 1.976(5) 3_565 ?
B1 B1 2.031(9) 25_566 ?
O1 B1 1.313(3) 3_565 ?
O1 B1 1.976(5) 2_665 ?

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
C1 C2 C1 114.6(6) 3_565 . ?
C1 C2 C1 114.6(6) 3_565 2_665 ?
C1 C2 C1 114.6(6) . 2_665 ?
C1 C2 C3 103.6(8) 3_565 . ?
C1 C2 C3 103.6(8) . . ?
C1 C2 C3 103.6(8) 2_665 . ?
C1 C2 C4 111.1(3) 3_565 . ?
C1 C2 C4 8.7(11) . . ?
C1 C2 C4 111.1(3) 2_665 . ?
C3 C2 C4 112.3(3) . . ?
C1 C2 C4 111.1(3) 3_565 2_665 ?
C1 C2 C4 111.1(3) . 2_665 ?
C1 C2 C4 8.7(11) 2_665 2_665 ?
C3 C2 C4 112.3(3) . 2_665 ?
C4 C2 C4 106.5(4) . 2_665 ?
C1 C2 C4 8.7(11) 3_565 3_565 ?
C1 C2 C4 111.1(3) . 3_565 ?
C1 C2 C4 111.1(3) 2_665 3_565 ?
C3 C2 C4 112.3(3) . 3_565 ?
C4 C2 C4 106.5(4) . 3_565 ?
C4 C2 C4 106.5(4) 2_665 3_565 ?
O1 C4 C2 108.1(4) . . ?
B1 B1 B1 60.000(1) 2_665 3_565 ?
B1 B1 O1 120.0(2) 2_665 . ?
B1 B1 O1 68.6(2) 3_565 . ?
B1 B1 O1 68.6(2) 2_665 2_665 ?
B1 B1 O1 120.0(2) 3_565 2_665 ?
O1 B1 O1 119.7(3) . 2_665 ?
B1 B1 B1 90.001(2) 2_665 26_456 ?
B1 B1 B1 74.45(14) 3_565 26_456 ?
O1 B1 B1 104.57(19) . 26_456 ?
O1 B1 B1 135.7(3) 2_665 26_456 ?
B1 B1 B1 74.44(14) 2_665 27_556 ?
B1 B1 B1 90.002(2) 3_565 27_556 ?
O1 B1 B1 135.7(3) . 27_556 ?
O1 B1 B1 104.57(19) 2_665 27_556 ?
B1 B1 B1 31.1(3) 26_456 27_556 ?
B1 B1 O1 35.15(6) 2_665 3_565 ?
B1 B1 O1 35.15(7) 3_565 3_565 ?
O1 B1 O1 84.8(2) . 3_565 ?
O1 B1 O1 84.8(2) 2_665 3_565 ?
B1 B1 O1 99.63(15) 26_456 3_565 ?
B1 B1 O1 99.63(15) 27_556 3_565 ?
B1 B1 B1 61.8(2) 2_665 25_566 ?
B1 B1 B1 61.8(2) 3_565 25_566 ?
O1 B1 B1 117.2(2) . 25_566 ?
O1 B1 B1 117.2(2) 2_665 25_566 ?
B1 B1 B1 28.2(2) 26_456 25_566 ?
B1 B1 B1 28.2(2) 27_556 25_566 ?
O1 B1 B1 76.2(3) 3_565 25_566 ?
B1 O1 B1 42.9(4) . 3_565 ?
B1 O1 C4 123.6(3) . . ?
B1 O1 C4 123.6(3) 3_565 . ?
B1 O1 B1 24.9(2) . 2_665 ?
B1 O1 B1 24.9(2) 3_565 2_665 ?
C4 O1 B1 113.5(3) . 2_665 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C4 O1 -64.4(7) 3_565 . . . ?
C1 C2 C4 O1 180.000(10) . . . . ?
C1 C2 C4 O1 64.4(7) 2_665 . . . ?
C3 C2 C4 O1 180.000(0) . . . . ?
C4 C2 C4 O1 56.7(4) 2_665 . . . ?
C4 C2 C4 O1 -56.7(4) 3_565 . . . ?
B1 B1 O1 B1 -32.18(16) 2_665 . . 3_565 ?
O1 B1 O1 B1 -113.2(3) 2_665 . . 3_565 ?
B1 B1 O1 B1 66.44(19) 26_456 . . 3_565 ?
B1 B1 O1 B1 66.3(4) 27_556 . . 3_565 ?
O1 B1 O1 B1 -32.18(16) 3_565 . . 3_565 ?
B1 B1 O1 B1 39.4(4) 25_566 . . 3_565 ?
B1 B1 O1 C4 72.9(2) 2_665 . . . ?
B1 B1 O1 C4 105.1(2) 3_565 . . . ?
O1 B1 O1 C4 -8.1(5) 2_665 . . . ?
B1 B1 O1 C4 171.54(13) 26_456 . . . ?
B1 B1 O1 C4 171.4(2) 27_556 . . . ?
O1 B1 O1 C4 72.9(2) 3_565 . . . ?
B1 B1 O1 C4 144.4(3) 25_566 . . . ?
B1 B1 O1 B1 32.18(16) 3_565 . . 2_665 ?
O1 B1 O1 B1 -81.0(4) 2_665 . . 2_665 ?
B1 B1 O1 B1 98.62(17) 26_456 . . 2_665 ?
B1 B1 O1 B1 98.5(4) 27_556 . . 2_665 ?
O1 B1 O1 B1 0.001(1) 3_565 . . 2_665 ?
B1 B1 O1 B1 71.5(4) 25_566 . . 2_665 ?
C2 C4 O1 B1 -26.0(3) . . . . ?
C2 C4 O1 B1 26.0(3) . . . 3_565 ?
C2 C4 O1 B1 -0.001(1) . . . 2_665 ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_ck41ck_115K
_database_code_depnum_ccdc_archive 'CCDC 1515552'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-21 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         'C10 H20 B2 O4'
_chemical_formula_sum            'C10 H20 B2 O4'
_chemical_formula_weight         225.89

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

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'

_cell_length_a                   8.8311(5)
_cell_length_b                   8.8311(5)
_cell_length_c                   27.5396(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1860.0(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    2781
_cell_measurement_theta_min      3.038
_cell_measurement_theta_max      26.87
_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.34
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_crystal_recrystallization_method 
;
 Gas phase diffusion of n-hexane into a solution in C6H6 at rt.
;



_exptl_special_details           
;
 The crystal was mounted on top of a human hair with perfluorether oil
 and placed in the nitrogen gas stream on the diffractometer at 290 K.
 The temperature was lowered to 115 K in eight 25 K steps.
 At each temperature a full measuement was perfomed (approx. 5.5 h per step).

 A combination of 15 sets of ω scans were used; each set at different \j,
 2θ or κ angles and each scan 0.8 deg in ω.
 Each frame was exposed for 10s. Nominal crystal to detector distance 43 mm.
;


_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_reflns_number            14504
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.047
_diffrn_reflns_theta_max         28.975
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             552
_reflns_number_gt                490
_reflns_threshold_expression     'I > 2σ(I)'


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;


_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
;
 SHELXS (G. M. Sheldrick, Acta Cryst., 2008, A64, 112--122)
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. (2008), A64, 112-122)'
;
_computing_molecular_graphics    
;
 K. Brandenburg, 1999, Diamond 3.2i, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;


_refine_special_details          
;
 The atoms C1 and C4 were refined using a constraint on the ADP (EADP).

 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.


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



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+2.2065P] 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         552
_refine_ls_number_parameters     37
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.1116(9) 0.1900(7) 0.1391(3) 0.0372(8) Uani 0.6667 1 d . . P . .
H1A H 0.0581 0.2607 0.1293 0.045 Uiso 0.6667 1 calc R U P . .
H1B H 0.2314 0.2440 0.1256 0.045 Uiso 0.6667 1 calc R U P . .
O1 O 0.1134(2) 0.17328(19) 0.19541(5) 0.0411(4) Uani 0.6667 1 d . . P . .
C4 C -0.1758(18) -0.0627(17) 0.1440(7) 0.0372(8) Uani 0.3333 1 d . . P . .
H4A H -0.1658 -0.0591 0.1795 0.056 Uiso 0.3333 1 calc R U P . .
H4B H -0.2214 0.0129 0.1335 0.056 Uiso 0.3333 1 calc R U P . .
H4C H -0.2556 -0.1830 0.1335 0.056 Uiso 0.3333 1 calc R U P . .
C2 C 0.0000 0.0000 0.12200(6) 0.0242(4) Uani 1 3 d S T P . .
C3 C 0.0000 0.0000 0.06672(7) 0.0315(5) Uani 1 3 d S T P . .
H3A H 0.1192 0.0425 0.0549 0.047 Uiso 0.3333 1 calc R U P . .
H3B H -0.0767 -0.1192 0.0549 0.047 Uiso 0.3333 1 calc R U P . .
H3C H -0.0425 0.0767 0.0549 0.047 Uiso 0.3333 1 calc R U P . .
B1 B -0.0109(5) 0.0654(5) 0.21894(12) 0.0285(7) Uani 0.3333 1 d . . 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 1.534(6) . ?
C1 O1 1.560(8) . ?
O1 B1 1.219(4) . ?
C4 C2 1.491(15) . ?
C2 C3 1.523(2) . ?
B1 O1 1.454(4) 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 O1 103.4(4) . . ?
B1 O1 C1 123.7(3) . . ?
C4 C2 C3 114.0(7) . . ?
C4 C2 C1 105.2(6) . . ?
C3 C2 C1 107.8(3) . . ?
O1 B1 O1 121.2(3) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 O1 B1 -35.8(5) . . . . ?
O1 C1 C2 C4 61.9(10) . . . . ?
O1 C1 C2 C3 -176.1(2) . . . . ?
C1 O1 B1 O1 0.7(5) . . . 2 ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_ck41ck1
_database_code_depnum_ccdc_archive 'CCDC 1515553'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-21 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         'C10 H20 B2 O4'
_chemical_formula_sum            'C10 H20 B2 O4'
_chemical_formula_weight         225.88

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

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

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

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

_cell_length_a                   15.2894(8)
_cell_length_b                   8.7342(4)
_cell_length_c                   19.2066(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.807(6)
_cell_angle_gamma                90
_cell_volume                     2467.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10778
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.34

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_crystal_recrystallization_method 
;
 Gas phase diffusion of n-hexane into a solution in C6H6 at rt.
;



_exptl_special_details           
;
 The crystal was mounted on top of a human hair with perfluorether oil
 and placed in the nitrogen gas stream on the diffractometer at 290 K.
 The temperature was lowered to 100K in eight 20-25K steps within 4 h
 (approx. 30 min per step).
 Once 100 K was reached the crystal was heated to 120 K and slowly cooled
 to 100 K in four 5 K steps (approx. 15 min per step); this sequence was
 repeated 6 times.

 Finally data collection was commenced covering nominally a full sphere
 of the reciprocal space.
 A combination of 19 sets of ω scans were used; each set at different \j,
 2θ or κ angles and each scan 0.8 deg in ω.
 Each frame was exposed for 15s. Nominal crystal to detector distance 55 mm.
;


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_reflns_number            12169
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.204
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12169
_reflns_number_gt                7891
_reflns_threshold_expression     'I > 2σ(I)'



_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
;
 SHELXT (Ver. 2014/4) (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. (2008), A64, 112-122)'
;
_computing_molecular_graphics    
;
 K. Brandenburg, 1999, Diamond 3.2i, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;


_refine_special_details          
;
The crystal is a 3-component twin and was refined accordingly;
 the twin factors refined to 0.1576(8) and 0.1083(7).

 The twinning occurs by 120° and 240° rotation about the c*-axis and is
 a reminiscence of a trigonal higher-symmetry high-temperature phase.

 For strcuture solution a dataset consisting only of reflections of the major
 component was used (Rint = 0.0397).

 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Methyl groups were treated as a rigid bodies and allowed to rotate about
 the E-CH3 bond.



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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         12169
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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 0.63813(13) 0.2163(2) 0.90752(10) 0.0185(4) Uani 1 1 d . . . . .
H1A H 0.6837 0.2978 0.9255 0.022 Uiso 1 1 calc R U . . .
H1B H 0.6654 0.1176 0.9277 0.022 Uiso 1 1 calc R U . . .
C2 C 0.55484(13) 0.2476(2) 0.93372(11) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.51255(14) 0.3955(2) 0.89787(10) 0.0183(4) Uani 1 1 d . . . . .
H3A H 0.4548 0.4145 0.9104 0.022 Uiso 1 1 calc R U . . .
H3B H 0.5541 0.4819 0.9169 0.022 Uiso 1 1 calc R U . . .
C4 C 0.58250(15) 0.2685(2) 1.01611(11) 0.0214(5) Uani 1 1 d . . . . .
H4A H 0.6144 0.1767 1.0392 0.032 Uiso 1 1 calc R U . . .
H4B H 0.5280 0.2847 1.0327 0.032 Uiso 1 1 calc R U . . .
H4C H 0.6227 0.3575 1.0290 0.032 Uiso 1 1 calc R U . . .
C5 C 0.48694(14) 0.1157(2) 0.91307(11) 0.0209(5) Uani 1 1 d . . . . .
H5A H 0.4662 0.1068 0.8603 0.031 Uiso 1 1 calc R U . . .
H5B H 0.4347 0.1357 0.9321 0.031 Uiso 1 1 calc R U . . .
H5C H 0.5164 0.0200 0.9337 0.031 Uiso 1 1 calc R U . . .
C6 C 0.46977(14) 0.4046(2) 0.57918(9) 0.0180(4) Uani 1 1 d . . . . .
H6A H 0.5247 0.4208 0.5622 0.022 Uiso 1 1 calc R U . . .
H6B H 0.4262 0.4877 0.5590 0.022 Uiso 1 1 calc R U . . .
C7 C 0.42707(13) 0.2509(2) 0.55114(11) 0.0157(4) Uani 1 1 d . . . . .
C8 C 0.49506(14) 0.1274(2) 0.58719(10) 0.0177(5) Uani 1 1 d . . . . .
H8A H 0.4679 0.0252 0.5733 0.021 Uiso 1 1 calc R U . . .
H8B H 0.5502 0.1358 0.5698 0.021 Uiso 1 1 calc R U . . .
C9 C 0.41200(15) 0.2434(2) 0.46922(11) 0.0209(5) Uani 1 1 d . . . . .
H9A H 0.3716 0.3269 0.4461 0.031 Uiso 1 1 calc R U . . .
H9B H 0.3842 0.1450 0.4511 0.031 Uiso 1 1 calc R U . . .
H9C H 0.4705 0.2534 0.4579 0.031 Uiso 1 1 calc R U . . .
C10 C 0.33716(13) 0.2297(2) 0.57021(11) 0.0223(5) Uani 1 1 d . . . . .
H10A H 0.3484 0.2288 0.6229 0.033 Uiso 1 1 calc R U . . .
H10B H 0.3094 0.1324 0.5502 0.033 Uiso 1 1 calc R U . . .
H10C H 0.2960 0.3142 0.5497 0.033 Uiso 1 1 calc R U . . .
B1 B 0.54534(15) 0.2955(2) 0.78910(11) 0.0166(5) Uani 1 1 d . . . . .
B2 B 0.51852(14) 0.2811(3) 0.69677(12) 0.0175(5) Uani 1 1 d . . . . .
O1 O 0.61609(8) 0.21048(15) 0.82941(6) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.49484(9) 0.38946(15) 0.81971(7) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.49443(9) 0.41218(14) 0.65720(6) 0.0183(3) Uani 1 1 d . . . . .
O4 O 0.52042(9) 0.14174(14) 0.66545(7) 0.0202(3) Uani 1 1 d . . . . .
C1A C 0.39161(14) 0.7689(2) 0.65552(11) 0.0197(5) Uani 1 1 d . . . . .
H1A1 H 0.4220 0.8670 0.6735 0.024 Uiso 1 1 calc R U . . .
H1A2 H 0.4377 0.6865 0.6683 0.024 Uiso 1 1 calc R U . . .
C2A C 0.31719(14) 0.7383(2) 0.69238(11) 0.0169(5) Uani 1 1 d . . . . .
C3A C 0.24461(14) 0.8615(2) 0.66589(10) 0.0197(5) Uani 1 1 d . . . . .
H3A1 H 0.1932 0.8426 0.6869 0.024 Uiso 1 1 calc R U . . .
H3A2 H 0.2706 0.9631 0.6827 0.024 Uiso 1 1 calc R U . . .
C4A C 0.35571(16) 0.7501(2) 0.77442(11) 0.0225(5) Uani 1 1 d . . . . .
H4A1 H 0.4003 0.6684 0.7915 0.034 Uiso 1 1 calc R U . . .
H4A2 H 0.3063 0.7396 0.7976 0.034 Uiso 1 1 calc R U . . .
H4A3 H 0.3852 0.8498 0.7868 0.034 Uiso 1 1 calc R U . . .
C5A C 0.27690(15) 0.5791(2) 0.67231(11) 0.0242(5) Uani 1 1 d . . . . .
H5A1 H 0.2552 0.5701 0.6195 0.036 Uiso 1 1 calc R U . . .
H5A2 H 0.2260 0.5634 0.6934 0.036 Uiso 1 1 calc R U . . .
H5A3 H 0.3237 0.5014 0.6911 0.036 Uiso 1 1 calc R U . . .
C6A C 0.11619(14) 0.7214(2) 0.34681(11) 0.0192(5) Uani 1 1 d . . . . .
H6A1 H 0.0706 0.8027 0.3285 0.023 Uiso 1 1 calc R U . . .
H6A2 H 0.0859 0.6212 0.3338 0.023 Uiso 1 1 calc R U . . .
C7A C 0.19271(14) 0.7370(2) 0.31091(11) 0.0160(4) Uani 1 1 d . . . . .
C8A C 0.24088(14) 0.8879(2) 0.33639(10) 0.0190(5) Uani 1 1 d . . . . .
H8A1 H 0.2941 0.8982 0.3168 0.023 Uiso 1 1 calc R U . . .
H8A2 H 0.1990 0.9740 0.3175 0.023 Uiso 1 1 calc R U . . .
C9A C 0.15345(15) 0.7401(2) 0.22878(11) 0.0210(5) Uani 1 1 d . . . . .
H9A1 H 0.1197 0.6452 0.2128 0.031 Uiso 1 1 calc R U . . .
H9A2 H 0.2031 0.7490 0.2057 0.031 Uiso 1 1 calc R U . . .
H9A3 H 0.1125 0.8279 0.2151 0.031 Uiso 1 1 calc R U . . .
C10A C 0.25954(14) 0.6031(2) 0.33294(11) 0.0202(5) Uani 1 1 d . . . . .
H10D H 0.2861 0.6043 0.3855 0.030 Uiso 1 1 calc R U . . .
H10E H 0.3080 0.6131 0.3087 0.030 Uiso 1 1 calc R U . . .
H10F H 0.2272 0.5063 0.3187 0.030 Uiso 1 1 calc R U . . .
B1A B 0.26785(16) 0.8193(3) 0.54725(12) 0.0199(5) Uani 1 1 d . . . . .
B2A B 0.22600(15) 0.8165(3) 0.45522(12) 0.0201(5) Uani 1 1 d . . . . .
O1A O 0.35598(10) 0.77634(16) 0.57741(7) 0.0210(3) Uani 1 1 d . . . . .
O2A O 0.21170(9) 0.86222(15) 0.58836(6) 0.0225(3) Uani 1 1 d . . . . .
O3A O 0.14918(10) 0.73305(16) 0.42502(8) 0.0223(4) Uani 1 1 d . . . . .
O4A O 0.27068(9) 0.89633(15) 0.41461(7) 0.0225(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.446(2) . ?
C1 C2 1.516(3) . ?
C2 C3 1.523(3) . ?
C2 C5 1.529(3) . ?
C2 C4 1.534(3) . ?
C3 O2 1.452(2) . ?
C6 O3 1.444(2) . ?
C6 C7 1.525(3) . ?
C7 C10 1.527(3) . ?
C7 C8 1.527(3) . ?
C7 C9 1.528(3) . ?
C8 O4 1.452(2) . ?
B1 O2 1.365(3) . ?
B1 O1 1.365(2) . ?
B1 B2 1.712(3) . ?
B2 O4 1.362(3) . ?
B2 O3 1.368(2) . ?
C1A O1A 1.451(2) . ?
C1A C2A 1.519(3) . ?
C2A C5A 1.528(3) . ?
C2A C4A 1.528(3) . ?
C2A C3A 1.530(3) . ?
C3A O2A 1.436(2) . ?
C6A O3A 1.452(2) . ?
C6A C7A 1.517(3) . ?
C7A C8A 1.524(3) . ?
C7A C9A 1.527(3) . ?
C7A C10A 1.535(3) . ?
C8A O4A 1.448(2) . ?
B1A O1A 1.366(3) . ?
B1A O2A 1.368(3) . ?
B1A B2A 1.708(3) . ?
B2A O4A 1.361(3) . ?
B2A O3A 1.370(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
O1 C1 C2 111.79(15) . . ?
C1 C2 C3 107.13(16) . . ?
C1 C2 C5 110.50(16) . . ?
C3 C2 C5 110.32(16) . . ?
C1 C2 C4 110.09(16) . . ?
C3 C2 C4 109.24(16) . . ?
C5 C2 C4 109.52(16) . . ?
O2 C3 C2 111.92(15) . . ?
O3 C6 C7 111.87(15) . . ?
C6 C7 C10 110.41(16) . . ?
C6 C7 C8 106.78(16) . . ?
C10 C7 C8 110.57(16) . . ?
C6 C7 C9 109.36(15) . . ?
C10 C7 C9 110.40(16) . . ?
C8 C7 C9 109.23(16) . . ?
O4 C8 C7 111.41(15) . . ?
O2 B1 O1 122.44(17) . . ?
O2 B1 B2 119.08(16) . . ?
O1 B1 B2 118.48(17) . . ?
O4 B2 O3 122.52(17) . . ?
O4 B2 B1 119.66(17) . . ?
O3 B2 B1 117.82(17) . . ?
B1 O1 C1 119.60(15) . . ?
B1 O2 C3 119.94(15) . . ?
B2 O3 C6 119.55(14) . . ?
B2 O4 C8 120.19(14) . . ?
O1A C1A C2A 111.82(16) . . ?
C1A C2A C5A 110.14(17) . . ?
C1A C2A C4A 109.98(17) . . ?
C5A C2A C4A 109.69(16) . . ?
C1A C2A C3A 106.80(16) . . ?
C5A C2A C3A 110.51(17) . . ?
C4A C2A C3A 109.68(16) . . ?
O2A C3A C2A 111.44(15) . . ?
O3A C6A C7A 111.73(16) . . ?
C6A C7A C8A 107.25(16) . . ?
C6A C7A C9A 109.64(17) . . ?
C8A C7A C9A 109.65(15) . . ?
C6A C7A C10A 110.13(16) . . ?
C8A C7A C10A 110.09(17) . . ?
C9A C7A C10A 110.04(16) . . ?
O4A C8A C7A 111.40(15) . . ?
O1A B1A O2A 122.15(18) . . ?
O1A B1A B2A 118.87(18) . . ?
O2A B1A B2A 118.97(18) . . ?
O4A B2A O3A 122.44(18) . . ?
O4A B2A B1A 118.72(17) . . ?
O3A B2A B1A 118.84(17) . . ?
B1A O1A C1A 119.98(16) . . ?
B1A O2A C3A 119.98(16) . . ?
B2A O3A C6A 119.44(15) . . ?
B2A O4A C8A 120.23(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -55.8(2) . . . . ?
O1 C1 C2 C5 64.4(2) . . . . ?
O1 C1 C2 C4 -174.47(15) . . . . ?
C1 C2 C3 O2 53.9(2) . . . . ?
C5 C2 C3 O2 -66.5(2) . . . . ?
C4 C2 C3 O2 173.09(16) . . . . ?
O3 C6 C7 C10 64.4(2) . . . . ?
O3 C6 C7 C8 -55.8(2) . . . . ?
O3 C6 C7 C9 -173.93(16) . . . . ?
C6 C7 C8 O4 54.7(2) . . . . ?
C10 C7 C8 O4 -65.5(2) . . . . ?
C9 C7 C8 O4 172.86(15) . . . . ?
O2 B1 B2 O4 -138.65(19) . . . . ?
O1 B1 B2 O4 40.6(3) . . . . ?
O2 B1 B2 O3 40.3(2) . . . . ?
O1 B1 B2 O3 -140.44(19) . . . . ?
O2 B1 O1 C1 1.4(3) . . . . ?
B2 B1 O1 C1 -177.83(16) . . . . ?
C2 C1 O1 B1 29.8(2) . . . . ?
O1 B1 O2 C3 -3.3(3) . . . . ?
B2 B1 O2 C3 175.90(16) . . . . ?
C2 C3 O2 B1 -26.0(2) . . . . ?
O4 B2 O3 C6 0.1(3) . . . . ?
B1 B2 O3 C6 -178.91(15) . . . . ?
C7 C6 O3 B2 30.0(2) . . . . ?
O3 B2 O4 C8 -0.9(3) . . . . ?
B1 B2 O4 C8 178.06(16) . . . . ?
C7 C8 O4 B2 -28.3(2) . . . . ?
O1A C1A C2A C5A 65.6(2) . . . . ?
O1A C1A C2A C4A -173.40(15) . . . . ?
O1A C1A C2A C3A -54.5(2) . . . . ?
C1A C2A C3A O2A 56.3(2) . . . . ?
C5A C2A C3A O2A -63.5(2) . . . . ?
C4A C2A C3A O2A 175.45(16) . . . . ?
O3A C6A C7A C8A -55.4(2) . . . . ?
O3A C6A C7A C9A -174.38(15) . . . . ?
O3A C6A C7A C10A 64.4(2) . . . . ?
C6A C7A C8A O4A 54.9(2) . . . . ?
C9A C7A C8A O4A 173.87(16) . . . . ?
C10A C7A C8A O4A -64.9(2) . . . . ?
O1A B1A B2A O4A -55.1(3) . . . . ?
O2A B1A B2A O4A 125.9(2) . . . . ?
O1A B1A B2A O3A 124.4(2) . . . . ?
O2A B1A B2A O3A -54.6(3) . . . . ?
O2A B1A O1A C1A 2.6(3) . . . . ?
B2A B1A O1A C1A -176.32(16) . . . . ?
C2A C1A O1A B1A 26.9(2) . . . . ?
O1A B1A O2A C3A -0.6(3) . . . . ?
B2A B1A O2A C3A 178.30(16) . . . . ?
C2A C3A O2A B1A -30.3(2) . . . . ?
O4A B2A O3A C6A 3.5(3) . . . . ?
B1A B2A O3A C6A -176.02(16) . . . . ?
C7A C6A O3A B2A 27.8(2) . . . . ?
O3A B2A O4A C8A -3.8(3) . . . . ?
B1A B2A O4A C8A 175.69(16) . . . . ?
C7A C8A O4A B2A -27.0(2) . . . . ?

_refine_diff_density_max         0.530
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_ck42ck
_database_code_depnum_ccdc_archive 'CCDC 1515554'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-21 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         'C8 H24 B2 N4'
_chemical_formula_sum            'C8 H24 B2 N4'
_chemical_formula_weight         197.93

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4204(5)
_cell_length_b                   8.8439(6)
_cell_length_c                   16.0580(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.851(5)
_cell_angle_gamma                90
_cell_volume                     1318.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    185(2)
_cell_measurement_reflns_used    10485
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.06


_exptl_crystal_recrystallization_method 
'B2(NMe2)4 was crystallised in situ. Pure B2(NMe2)4 was enclosed in a glass capillary of 1.0 mm outer diameter that narrows at one end into a cone. The capillary was filled with ca. 0.1 /mL of B2(NMe2)4. The capillary was  flame sealed and glued into a brass pin that was mounted on the goniometer head. A part of the conical section of this capillary was centered in the  X-ray beam (0.5 mm dia.), so that a conical section of the capillary filled  with B2(NMe2)4 was exposed to the X-ray beam (bottom diameter: 0.42 mm, top diameter: 0.19 mm). The axis of the capillary was aligned parallel to nitrogen gas stream of the cryostat. The temperature was gradually (within 3 h) lowered from rt to 200 K whereupon the B2(NMe2)4 crystallised upon shock-cooling with a drop of liquid nitrogen; the poly crystalline mass was found to melt at approx. 205 K. Sequences of cooling to 200 - 195 K, annealing, shock-cooling, reheating to 210K were repeated until the diffraction pattern indicated that a reasonably single crystalline sample had formed. Finally the temperature was lowered to 185 K.'


_exptl_special_details           
;
 The diffraction data were collected employing only phi scans in order to 
 maintain the parallel orientation of the sample capillary in the nitrogen gas
 stream and to ensure that the same part of the sample was measured during the 
 entire measurement. For mechanical restrictions of the instrument used that 
 resulted in a data collection strategy using four set of /p scans around 360°
 (each 1 deg in /p) at four different detector positions
 (at positive and negative angles).  Each frame was exposed for 15s at a
 nominal crystal to detector distance of 75 mm.
 To improve the statistics this set of measurement was repeated for more
 than twice.

 However, the mechanical restrictions of the instrument used did not allow to
 collect data under the given restrictions to more than 92.2% completeness.

 Indexation was conducted considering only reflections above a resolution of 
 2.56 Ang., where 70% of all reflections could be indexed with a single cell;
 using three identical cells 91% could be indexed.
 However, only the major component was integrated and used in structure 
 solution and refinement. 
 N.B.: An attempted refinement as a non-merohedral twin including all three 
 indexed components did not improve the quality of the structure and was 
 abandoned.
;




_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.997
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
 (compiled Dec 19 2012,11:08:27)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_diffrn_ambient_temperature      185(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       π-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_reflns_number            37371
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             2143
_reflns_number_gt                1954
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
 (compiled Dec 19 2012,11:08:27)
;
_computing_cell_refinement       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
 (compiled Dec 19 2012,11:08:27)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
 (compiled Dec 19 2012,11:08:27)
;
_computing_structure_solution    
;
 SHELXT (Ver. 2014/4) (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. (2008), A64, 112-122)'
;
_computing_molecular_graphics    
;
 K. Brandenburg, 1999, Diamond 3.2i, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;



_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.5 times the equivalent isotropic
 displacement parameter of the parent atom.
 Methyl groups were treated as a rigid bodies and allowed to rotate about
 the E-CH3 bond.

 11 refections of bad Fo/Fc ratio have been omitted.

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




_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.6341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         2143
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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 0.7248(3) 0.6253(3) 0.79999(14) 0.0611(7) Uani 1 1 d . . . . .
H1A H 0.7295 0.5262 0.8277 0.092 Uiso 1 1 calc R U . . .
H1B H 0.7006 0.7028 0.8389 0.092 Uiso 1 1 calc R U . . .
H1C H 0.8184 0.6488 0.7843 0.092 Uiso 1 1 calc R U . . .
C2 C 0.4767(3) 0.5704(4) 0.74327(18) 0.0671(8) Uani 1 1 d . . . . .
H2A H 0.4138 0.5420 0.6905 0.101 Uiso 1 1 calc R U . . .
H2B H 0.4314 0.6518 0.7708 0.101 Uiso 1 1 calc R U . . .
H2C H 0.4919 0.4825 0.7809 0.101 Uiso 1 1 calc R U . . .
C3 C 0.3948(3) 0.7366(4) 0.57265(18) 0.0651(8) Uani 1 1 d . . . . .
H3A H 0.3819 0.7581 0.6308 0.098 Uiso 1 1 calc R U . . .
H3B H 0.3287 0.6557 0.5492 0.098 Uiso 1 1 calc R U . . .
H3C H 0.3741 0.8280 0.5382 0.098 Uiso 1 1 calc R U . . .
C4 C 0.5746(3) 0.6925(3) 0.48691(14) 0.0568(7) Uani 1 1 d . . . . .
H4A H 0.6755 0.6638 0.4882 0.085 Uiso 1 1 calc R U . . .
H4B H 0.5585 0.7947 0.4637 0.085 Uiso 1 1 calc R U . . .
H4C H 0.5117 0.6211 0.4513 0.085 Uiso 1 1 calc R U . . .
C5 C 0.8213(3) 0.9323(3) 0.60162(16) 0.0538(6) Uani 1 1 d . . . . .
H5A H 0.7827 0.9645 0.5438 0.081 Uiso 1 1 calc R U . . .
H5B H 0.8926 1.0061 0.6281 0.081 Uiso 1 1 calc R U . . .
H5C H 0.7427 0.9254 0.6343 0.081 Uiso 1 1 calc R U . . .
C6 C 1.0010(3) 0.7899(3) 0.54732(16) 0.0570(7) Uani 1 1 d . . . . .
H6A H 1.0272 0.6865 0.5341 0.085 Uiso 1 1 calc R U . . .
H6B H 1.0860 0.8420 0.5779 0.085 Uiso 1 1 calc R U . . .
H6C H 0.9650 0.8442 0.4947 0.085 Uiso 1 1 calc R U . . .
C7 C 1.0681(2) 0.5092(3) 0.65852(16) 0.0566(7) Uani 1 1 d . . . . .
H7A H 1.0996 0.4632 0.6092 0.085 Uiso 1 1 calc R U . . .
H7B H 1.1018 0.4474 0.7087 0.085 Uiso 1 1 calc R U . . .
H7C H 1.1085 0.6112 0.6672 0.085 Uiso 1 1 calc R U . . .
C8 C 0.8469(3) 0.3732(3) 0.65852(16) 0.0546(6) Uani 1 1 d . . . . .
H8A H 0.7424 0.3853 0.6540 0.082 Uiso 1 1 calc R U . . .
H8B H 0.8875 0.3362 0.7151 0.082 Uiso 1 1 calc R U . . .
H8C H 0.8672 0.3004 0.6161 0.082 Uiso 1 1 calc R U . . .
B1 B 0.6500(2) 0.6553(3) 0.64339(14) 0.0352(5) Uani 1 1 d . . . . .
B2 B 0.8284(2) 0.6528(3) 0.62927(13) 0.0325(5) Uani 1 1 d . . . . .
N1 N 0.61527(18) 0.6225(2) 0.72477(11) 0.0438(5) Uani 1 1 d . . . . .
N2 N 0.54234(17) 0.6892(2) 0.57234(11) 0.0442(5) Uani 1 1 d . . . . .
N3 N 0.88942(17) 0.7853(2) 0.59962(11) 0.0392(5) Uani 1 1 d . . . . .
N4 N 0.91107(17) 0.5175(2) 0.64431(11) 0.0399(5) 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 1.449(3) . ?
C2 N1 1.462(3) . ?
C3 N2 1.453(3) . ?
C4 N2 1.455(3) . ?
C5 N3 1.452(3) . ?
C6 N3 1.454(3) . ?
C7 N4 1.460(3) . ?
C8 N4 1.447(3) . ?
B1 N2 1.422(3) . ?
B1 N1 1.430(3) . ?
B1 B2 1.735(3) . ?
B2 N3 1.423(3) . ?
B2 N4 1.425(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
N2 B1 N1 122.20(18) . . ?
N2 B1 B2 118.13(17) . . ?
N1 B1 B2 119.67(17) . . ?
N3 B2 N4 120.53(17) . . ?
N3 B2 B1 119.29(18) . . ?
N4 B2 B1 120.14(18) . . ?
B1 N1 C1 121.13(17) . . ?
B1 N1 C2 126.95(19) . . ?
C1 N1 C2 111.70(18) . . ?
B1 N2 C3 127.52(19) . . ?
B1 N2 C4 121.67(17) . . ?
C3 N2 C4 110.60(18) . . ?
B2 N3 C5 121.64(17) . . ?
B2 N3 C6 126.11(19) . . ?
C5 N3 C6 110.72(18) . . ?
B2 N4 C8 122.43(17) . . ?
B2 N4 C7 125.36(19) . . ?
C8 N4 C7 111.73(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 B1 B2 N3 58.7(3) . . . . ?
N1 B1 B2 N3 -121.8(2) . . . . ?
N2 B1 B2 N4 -119.0(2) . . . . ?
N1 B1 B2 N4 60.5(3) . . . . ?
N2 B1 N1 C1 -164.5(2) . . . . ?
B2 B1 N1 C1 16.0(3) . . . . ?
N2 B1 N1 C2 21.4(4) . . . . ?
B2 B1 N1 C2 -158.1(2) . . . . ?
N1 B1 N2 C3 18.3(4) . . . . ?
B2 B1 N2 C3 -162.3(2) . . . . ?
N1 B1 N2 C4 -167.4(2) . . . . ?
B2 B1 N2 C4 12.0(3) . . . . ?
N4 B2 N3 C5 -166.0(2) . . . . ?
B1 B2 N3 C5 16.3(3) . . . . ?
N4 B2 N3 C6 29.4(3) . . . . ?
B1 B2 N3 C6 -148.3(2) . . . . ?
N3 B2 N4 C8 -167.78(19) . . . . ?
B1 B2 N4 C8 9.9(3) . . . . ?
N3 B2 N4 C7 20.9(3) . . . . ?
B1 B2 N4 C7 -161.46(19) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_ck57ck
_database_code_depnum_ccdc_archive 'CCDC 1515555'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-21 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         'C12 H24 B2 O4'
_chemical_formula_sum            'C12 H24 B2 O4'
_chemical_formula_weight         253.93

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

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

_cell_length_a                   10.1407(7)
_cell_length_b                   14.8953(9)
_cell_length_c                   19.4745(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.798(6)
_cell_angle_gamma                90
_cell_volume                     2907.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4884
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      28.70

_exptl_crystal_description       'fragment of prism'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_recrystallization_method 
;
 From solution in n-pentane at -40 deg C.
;



_exptl_special_details           
;
 The crystal was mounted on top of a human hair with perfluorether oil
 and placed in a cold nitrogen gas stream on the diffractometer.

 The collected data cover nominally a full sphere of the reciprocal space.
 A combination of 13 sets of ω scans were used; each set at different \j,
 2θ or κ angles and each scan 1.0 deg in ω.
 Each frame was exposed for 10s. Nominal crystal to detector distance 43 mm.
;



_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_ambient_environment      N~2~
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_reflns_number            31836
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.450
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6886
_reflns_number_gt                4871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.998

_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, Agilent Technologies,
 Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
 (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
 CrysAlisPro, Rigaku Oxford Diffraction, 2015,
 Version 1.171.38.43, 2015
;
_computing_data_reduction        
;
 CrysAlisPro, Rigaku Oxford Diffraction, 2015,
 Version 1.171.38.43, 2015
;
_computing_structure_solution    
;
 SHELXT (Ver. 2014/4) (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3--8)
;
_computing_molecular_graphics    
;
 K. Brandenburg, 1999, Diamond 3.2i, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
;
 WinGX v2014.1 (L. J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854.)
;


_refine_special_details          
;
 Two disordered pinacolato groups was refined using split atom models
 (0.47(2) and 0.52(1) SOFs of main components).
 Similarity restraints were applied on the H3C-C distances of the disordered
 groups (SADI). A common ADP was refined for each disordered atom pair (EADP).


 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Methyl groups were treated as rigid bodies and allowed to rotate about
 the E-CH3 bond but not to tip.


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




_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.2888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6886
_refine_ls_number_parameters     412
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.4579(5) 0.1668(3) 0.4058(3) 0.0204(10) Uani 1 1 d . . . . .
C2 C 0.3730(5) 0.0888(3) 0.3685(3) 0.0203(10) Uani 1 1 d . . . . .
C3 C 0.4779(4) 0.2466(3) 0.3603(2) 0.0196(9) Uani 1 1 d . . . . .
H3A H 0.3911 0.2730 0.3420 0.029 Uiso 1 1 calc R U . . .
H3B H 0.5222 0.2269 0.3216 0.029 Uiso 1 1 calc R U . . .
H3C H 0.5335 0.2916 0.3878 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5921(4) 0.1351(3) 0.4451(2) 0.0191(9) Uani 1 1 d . . . . .
H4A H 0.6343 0.1842 0.4739 0.029 Uiso 1 1 calc R U . . .
H4B H 0.6502 0.1168 0.4118 0.029 Uiso 1 1 calc R U . . .
H4C H 0.5777 0.0840 0.4748 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2703(4) 0.1210(3) 0.3073(2) 0.0213(9) Uani 1 1 d . . . . .
H5A H 0.2111 0.0712 0.2903 0.032 Uiso 1 1 calc R U . . .
H5B H 0.3168 0.1423 0.2698 0.032 Uiso 1 1 calc R U . . .
H5C H 0.2175 0.1702 0.3226 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4512(5) 0.0094(3) 0.3473(2) 0.0217(9) Uani 1 1 d . . . . .
H6A H 0.5072 -0.0154 0.3884 0.032 Uiso 1 1 calc R U . . .
H6B H 0.5078 0.0291 0.3136 0.032 Uiso 1 1 calc R U . . .
H6C H 0.3890 -0.0368 0.3262 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0316(5) 0.0886(3) 0.5948(3) 0.0201(10) Uani 1 1 d D . . . .
C8 C 0.1262(5) 0.1612(3) 0.6357(3) 0.0202(10) Uani 1 1 d D . . . .
B1 B 0.2935(6) 0.1273(4) 0.4693(3) 0.0199(11) Uani 1 1 d . . . . .
B2 B 0.1981(6) 0.1264(4) 0.5343(3) 0.0210(12) Uani 1 1 d . . . . .
O1 O 0.3791(3) 0.19603(18) 0.45860(13) 0.0150(6) Uani 1 1 d . . . . .
O2 O 0.2945(3) 0.05840(18) 0.42153(14) 0.0161(6) Uani 1 1 d . . . . .
O3 O 0.2421(15) 0.1626(11) 0.5973(8) 0.034(3) Uani 0.47(2) 1 d . . P A 1
O4 O 0.0762(14) 0.0888(10) 0.5267(7) 0.030(3) Uani 0.47(2) 1 d . . P A 1
C9 C -0.1135(17) 0.1155(19) 0.5838(10) 0.032(3) Uani 0.47(2) 1 d D . P A 1
H9A H -0.1236 0.1742 0.5610 0.048 Uiso 0.47(2) 1 calc R U P A 1
H9B H -0.1452 0.1189 0.6288 0.048 Uiso 0.47(2) 1 calc R U P A 1
H9C H -0.1660 0.0707 0.5545 0.048 Uiso 0.47(2) 1 calc R U P A 1
C10 C 0.051(2) -0.0057(13) 0.6239(15) 0.037(3) Uani 0.47(2) 1 d D . P A 1
H10A H -0.0092 -0.0470 0.5950 0.055 Uiso 0.47(2) 1 calc R U P A 1
H10B H 0.0308 -0.0067 0.6715 0.055 Uiso 0.47(2) 1 calc R U P A 1
H10C H 0.1436 -0.0245 0.6239 0.055 Uiso 0.47(2) 1 calc R U P A 1
C11 C 0.070(2) 0.2546(11) 0.6339(10) 0.033(3) Uani 0.47(2) 1 d D . P A 1
H11A H 0.1378 0.2960 0.6570 0.050 Uiso 0.47(2) 1 calc R U P A 1
H11B H -0.0080 0.2555 0.6581 0.050 Uiso 0.47(2) 1 calc R U P A 1
H11C H 0.0432 0.2734 0.5856 0.050 Uiso 0.47(2) 1 calc R U P A 1
C12 C 0.184(3) 0.132(3) 0.7087(10) 0.037(4) Uani 0.47(2) 1 d D . P A 1
H12A H 0.2339 0.0763 0.7067 0.055 Uiso 0.47(2) 1 calc R U P A 1
H12B H 0.1115 0.1229 0.7359 0.055 Uiso 0.47(2) 1 calc R U P A 1
H12C H 0.2440 0.1792 0.7306 0.055 Uiso 0.47(2) 1 calc R U P A 1
O3' O 0.1086(13) 0.0624(8) 0.5406(7) 0.032(2) Uani 0.53(2) 1 d . . P A 2
O4' O 0.2068(13) 0.1890(9) 0.5844(7) 0.030(2) Uani 0.53(2) 1 d . . P A 2
C9' C -0.1022(15) 0.1219(16) 0.5612(9) 0.032(3) Uani 0.53(2) 1 d D . P A 2
H9'1 H -0.1495 0.0737 0.5333 0.048 Uiso 0.53(2) 1 calc R U P A 2
H9'2 H -0.0903 0.1731 0.5311 0.048 Uiso 0.53(2) 1 calc R U P A 2
H9'3 H -0.1542 0.1407 0.5972 0.048 Uiso 0.53(2) 1 calc R U P A 2
C10' C 0.016(2) 0.0045(12) 0.6366(13) 0.037(3) Uani 0.53(2) 1 d D . P A 2
H10D H -0.0351 -0.0404 0.6067 0.055 Uiso 0.53(2) 1 calc R U P A 2
H10E H -0.0321 0.0192 0.6753 0.055 Uiso 0.53(2) 1 calc R U P A 2
H10F H 0.1039 -0.0197 0.6550 0.055 Uiso 0.53(2) 1 calc R U P A 2
C11' C 0.051(2) 0.2433(10) 0.6545(10) 0.033(3) Uani 0.53(2) 1 d D . P A 2
H11D H 0.1143 0.2887 0.6756 0.050 Uiso 0.53(2) 1 calc R U P A 2
H11E H -0.0086 0.2263 0.6876 0.050 Uiso 0.53(2) 1 calc R U P A 2
H11F H -0.0022 0.2680 0.6124 0.050 Uiso 0.53(2) 1 calc R U P A 2
C12' C 0.217(2) 0.127(2) 0.6987(10) 0.037(4) Uani 0.53(2) 1 d D . P A 2
H12D H 0.2555 0.0696 0.6880 0.055 Uiso 0.53(2) 1 calc R U P A 2
H12E H 0.1665 0.1199 0.7372 0.055 Uiso 0.53(2) 1 calc R U P A 2
H12F H 0.2894 0.1708 0.7119 0.055 Uiso 0.53(2) 1 calc R U P A 2
C1A C 0.8612(5) 0.4072(3) 0.3647(3) 0.0198(10) Uani 1 1 d . . . . .
C2A C 0.9559(5) 0.3378(3) 0.4062(3) 0.0218(10) Uani 1 1 d . . . . .
C3A C 0.8095(5) 0.3812(3) 0.2901(2) 0.0231(10) Uani 1 1 d . . . . .
H3A1 H 0.7615 0.3240 0.2894 0.035 Uiso 1 1 calc R U . . .
H3A2 H 0.8847 0.3749 0.2643 0.035 Uiso 1 1 calc R U . . .
H3A3 H 0.7488 0.4278 0.2684 0.035 Uiso 1 1 calc R U . . .
C4A C 0.9172(5) 0.5026(3) 0.3671(2) 0.0201(9) Uani 1 1 d . . . . .
H4A1 H 0.8475 0.5441 0.3461 0.030 Uiso 1 1 calc R U . . .
H4A2 H 0.9928 0.5049 0.3413 0.030 Uiso 1 1 calc R U . . .
H4A3 H 0.9470 0.5199 0.4155 0.030 Uiso 1 1 calc R U . . .
C5A C 0.9338(4) 0.2414(3) 0.3801(2) 0.0202(9) Uani 1 1 d . . . . .
H5A1 H 0.9846 0.2001 0.4134 0.030 Uiso 1 1 calc R U . . .
H5A2 H 0.9639 0.2354 0.3349 0.030 Uiso 1 1 calc R U . . .
H5A3 H 0.8386 0.2267 0.3754 0.030 Uiso 1 1 calc R U . . .
C6A C 1.1048(4) 0.3607(3) 0.4140(2) 0.0227(9) Uani 1 1 d . . . . .
H6A1 H 1.1199 0.4205 0.4347 0.034 Uiso 1 1 calc R U . . .
H6A2 H 1.1337 0.3601 0.3683 0.034 Uiso 1 1 calc R U . . .
H6A3 H 1.1561 0.3163 0.4442 0.034 Uiso 1 1 calc R U . . .
C7A C 0.6219(5) 0.3421(3) 0.6346(3) 0.0218(11) Uani 1 1 d D . . . .
C8A C 0.5304(5) 0.4175(3) 0.5952(3) 0.0216(11) Uani 1 1 d D . . . .
B1A B 0.7886(6) 0.3760(4) 0.4687(3) 0.0206(12) Uani 1 1 d . . . . .
B2A B 0.6939(6) 0.3775(4) 0.5334(3) 0.0217(12) Uani 1 1 d . . . . .
O1A O 0.9168(3) 0.34014(18) 0.47549(14) 0.0151(6) Uani 1 1 d . . . . .
O2A O 0.7477(3) 0.40913(18) 0.40254(15) 0.0155(6) Uani 1 1 d . . . . .
O3A O 0.6092(10) 0.4466(7) 0.5419(5) 0.034(2) Uani 0.517(14) 1 d . . P B 3
O4A O 0.6965(10) 0.3125(6) 0.5812(5) 0.031(2) Uani 0.517(14) 1 d . . P B 3
C9A C 0.5379(18) 0.2613(10) 0.6506(9) 0.032(3) Uani 0.517(14) 1 d D . P B 3
H9A1 H 0.4832 0.2406 0.6077 0.048 Uiso 0.517(14) 1 calc R U P B 3
H9A2 H 0.4797 0.2790 0.6841 0.048 Uiso 0.517(14) 1 calc R U P B 3
H9A3 H 0.5970 0.2127 0.6703 0.048 Uiso 0.517(14) 1 calc R U P B 3
C10A C 0.7146(19) 0.3730(19) 0.6973(8) 0.033(3) Uani 0.517(14) 1 d D . P B 3
H10G H 0.7808 0.3261 0.7118 0.050 Uiso 0.517(14) 1 calc R U P B 3
H10H H 0.6636 0.3853 0.7352 0.050 Uiso 0.517(14) 1 calc R U P B 3
H10I H 0.7602 0.4279 0.6861 0.050 Uiso 0.517(14) 1 calc R U P B 3
C11A C 0.3950(12) 0.3899(10) 0.5577(7) 0.034(2) Uani 0.517(14) 1 d D . P B 3
H11G H 0.3507 0.4421 0.5336 0.050 Uiso 0.517(14) 1 calc R U P B 3
H11H H 0.3408 0.3669 0.5913 0.050 Uiso 0.517(14) 1 calc R U P B 3
H11I H 0.4058 0.3430 0.5237 0.050 Uiso 0.517(14) 1 calc R U P B 3
C12A C 0.5145(16) 0.5006(10) 0.6391(9) 0.039(3) Uani 0.517(14) 1 d D . P B 3
H12G H 0.6028 0.5231 0.6592 0.059 Uiso 0.517(14) 1 calc R U P B 3
H12H H 0.4643 0.4847 0.6766 0.059 Uiso 0.517(14) 1 calc R U P B 3
H12I H 0.4663 0.5472 0.6099 0.059 Uiso 0.517(14) 1 calc R U P B 3
O3B O 0.5737(10) 0.4136(7) 0.5272(5) 0.030(2) Uani 0.483(14) 1 d . . P B 4
O4B O 0.7389(9) 0.3414(6) 0.5968(5) 0.028(2) Uani 0.483(14) 1 d . . P B 4
C9B C 0.566(2) 0.2495(10) 0.6326(9) 0.032(3) Uani 0.483(14) 1 d D . P B 4
H9B1 H 0.5376 0.2314 0.5842 0.048 Uiso 0.483(14) 1 calc R U P B 4
H9B2 H 0.4888 0.2483 0.6575 0.048 Uiso 0.483(14) 1 calc R U P B 4
H9B3 H 0.6342 0.2079 0.6548 0.048 Uiso 0.483(14) 1 calc R U P B 4
C10B C 0.682(2) 0.367(2) 0.7086(9) 0.033(3) Uani 0.483(14) 1 d D . P B 4
H10J H 0.7389 0.3176 0.7292 0.050 Uiso 0.483(14) 1 calc R U P B 4
H10K H 0.6098 0.3767 0.7362 0.050 Uiso 0.483(14) 1 calc R U P B 4
H10L H 0.7348 0.4216 0.7082 0.050 Uiso 0.483(14) 1 calc R U P B 4
C12B C 0.5585(17) 0.5100(10) 0.6238(10) 0.039(3) Uani 0.483(14) 1 d D . P B 4
H12J H 0.6532 0.5241 0.6247 0.059 Uiso 0.483(14) 1 calc R U P B 4
H12K H 0.5369 0.5129 0.6711 0.059 Uiso 0.483(14) 1 calc R U P B 4
H12L H 0.5039 0.5536 0.5944 0.059 Uiso 0.483(14) 1 calc R U P B 4
C11B C 0.3847(13) 0.3919(11) 0.5875(7) 0.034(2) Uani 0.483(14) 1 d D . P B 4
H11J H 0.3306 0.4388 0.5615 0.050 Uiso 0.483(14) 1 calc R U P B 4
H11K H 0.3584 0.3853 0.6336 0.050 Uiso 0.483(14) 1 calc R U P B 4
H11L H 0.3707 0.3349 0.5623 0.050 Uiso 0.483(14) 1 calc R U P B 4


_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 O1 1.462(6) . ?
C1 C3 1.515(6) . ?
C1 C4 1.531(6) . ?
C1 C2 1.557(7) . ?
C2 O2 1.468(6) . ?
C2 C6 1.516(7) . ?
C2 C5 1.536(6) . ?
C7 O3' 1.460(14) . ?
C7 O4 1.466(15) . ?
C7 C9' 1.498(14) . ?
C7 C9 1.509(16) . ?
C7 C10 1.516(16) . ?
C7 C10' 1.516(14) . ?
C7 C8 1.578(7) . ?
C8 O4' 1.444(14) . ?
C8 O3 1.485(17) . ?
C8 C11 1.503(15) . ?
C8 C12' 1.505(15) . ?
C8 C12 1.514(17) . ?
C8 C11' 1.518(14) . ?
B1 O1 1.378(7) . ?
B1 O2 1.386(7) . ?
B1 B2 1.707(5) . ?
B2 O3' 1.336(14) . ?
B2 O4' 1.343(14) . ?
B2 O4 1.344(15) . ?
B2 O3 1.352(17) . ?
C1A O2A 1.459(6) . ?
C1A C3A 1.517(6) . ?
C1A C4A 1.528(6) . ?
C1A C2A 1.552(7) . ?
C2A O1A 1.465(6) . ?
C2A C5A 1.528(6) . ?
C2A C6A 1.533(7) . ?
C7A O4A 1.447(10) . ?
C7A O4B 1.490(11) . ?
C7A C9B 1.490(15) . ?
C7A C10A 1.495(15) . ?
C7A C10B 1.520(16) . ?
C7A C9A 1.534(14) . ?
C7A C8A 1.578(7) . ?
C8A O3B 1.458(11) . ?
C8A O3A 1.468(11) . ?
C8A C12B 1.499(14) . ?
C8A C11A 1.510(13) . ?
C8A C11B 1.511(13) . ?
C8A C12A 1.528(14) . ?
B1A O2A 1.383(7) . ?
B1A O1A 1.393(7) . ?
B1A B2A 1.696(5) . ?
B2A O3B 1.321(12) . ?
B2A O4A 1.341(10) . ?
B2A O4B 1.360(11) . ?
B2A O3A 1.367(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C3 108.3(4) . . ?
O1 C1 C4 106.2(4) . . ?
C3 C1 C4 110.2(4) . . ?
O1 C1 C2 103.2(4) . . ?
C3 C1 C2 115.3(4) . . ?
C4 C1 C2 112.9(4) . . ?
O2 C2 C6 108.2(4) . . ?
O2 C2 C5 105.5(4) . . ?
C6 C2 C5 110.6(4) . . ?
O2 C2 C1 102.9(4) . . ?
C6 C2 C1 115.7(4) . . ?
C5 C2 C1 113.0(4) . . ?
O3' C7 C9' 108.7(8) . . ?
O4 C7 C9 107.5(8) . . ?
O4 C7 C10 107.5(10) . . ?
C9 C7 C10 111.5(13) . . ?
O3' C7 C10' 106.3(8) . . ?
C9' C7 C10' 110.2(12) . . ?
O3' C7 C8 101.4(6) . . ?
O4 C7 C8 101.9(6) . . ?
C9' C7 C8 115.7(10) . . ?
C9 C7 C8 113.2(12) . . ?
C10 C7 C8 114.4(13) . . ?
C10' C7 C8 113.7(11) . . ?
O3 C8 C11 107.6(9) . . ?
O4' C8 C12' 108.5(11) . . ?
O3 C8 C12 104.7(12) . . ?
C11 C8 C12 112.0(17) . . ?
O4' C8 C11' 107.1(7) . . ?
C12' C8 C11' 110.0(14) . . ?
O4' C8 C7 102.3(6) . . ?
O3 C8 C7 102.9(7) . . ?
C11 C8 C7 115.1(11) . . ?
C12' C8 C7 115.6(15) . . ?
C12 C8 C7 113.4(17) . . ?
C11' C8 C7 112.6(9) . . ?
O1 B1 O2 112.3(5) . . ?
O1 B1 B2 124.0(4) . . ?
O2 B1 B2 123.7(4) . . ?
O3' B2 O4' 113.6(9) . . ?
O4 B2 O3 115.9(10) . . ?
O3' B2 B1 122.9(6) . . ?
O4' B2 B1 123.5(7) . . ?
O4 B2 B1 122.5(7) . . ?
O3 B2 B1 121.7(8) . . ?
B1 O1 C1 108.0(4) . . ?
B1 O2 C2 107.7(4) . . ?
B2 O3 C8 105.9(11) . . ?
B2 O4 C7 107.8(9) . . ?
B2 O3' C7 108.7(9) . . ?
B2 O4' C8 108.8(9) . . ?
O2A C1A C3A 107.8(4) . . ?
O2A C1A C4A 106.5(4) . . ?
C3A C1A C4A 109.9(4) . . ?
O2A C1A C2A 102.9(4) . . ?
C3A C1A C2A 115.1(4) . . ?
C4A C1A C2A 114.0(4) . . ?
O1A C2A C5A 106.4(4) . . ?
O1A C2A C6A 107.7(4) . . ?
C5A C2A C6A 109.6(4) . . ?
O1A C2A C1A 103.3(4) . . ?
C5A C2A C1A 113.9(4) . . ?
C6A C2A C1A 115.2(4) . . ?
O4B C7A C9B 108.1(7) . . ?
O4A C7A C10A 110.4(9) . . ?
O4B C7A C10B 103.8(8) . . ?
C9B C7A C10B 110.1(13) . . ?
O4A C7A C9A 105.9(6) . . ?
C10A C7A C9A 112.0(11) . . ?
O4A C7A C8A 101.6(5) . . ?
O4B C7A C8A 102.6(5) . . ?
C9B C7A C8A 116.9(9) . . ?
C10A C7A C8A 115.3(12) . . ?
C10B C7A C8A 114.2(13) . . ?
C9A C7A C8A 110.7(9) . . ?
O3B C8A C12B 107.9(8) . . ?
O3A C8A C11A 106.9(6) . . ?
O3B C8A C11B 109.0(6) . . ?
C12B C8A C11B 113.4(9) . . ?
O3A C8A C12A 105.8(7) . . ?
C11A C8A C12A 109.0(9) . . ?
O3B C8A C7A 100.2(5) . . ?
O3A C8A C7A 102.2(5) . . ?
C12B C8A C7A 114.1(9) . . ?
C11A C8A C7A 117.7(7) . . ?
C11B C8A C7A 111.2(7) . . ?
C12A C8A C7A 114.1(8) . . ?
O2A B1A O1A 111.6(5) . . ?
O2A B1A B2A 124.3(4) . . ?
O1A B1A B2A 124.1(4) . . ?
O3B B2A O4B 114.8(7) . . ?
O4A B2A O3A 113.9(7) . . ?
O3B B2A B1A 123.9(6) . . ?
O4A B2A B1A 123.5(5) . . ?
O4B B2A B1A 121.3(5) . . ?
O3A B2A B1A 122.6(5) . . ?
B1A O1A C2A 107.6(4) . . ?
B1A O2A C1A 108.5(4) . . ?
B2A O3A C8A 106.5(7) . . ?
B2A O4A C7A 108.8(7) . . ?
B2A O3B C8A 109.6(7) . . ?
B2A O4B C7A 105.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -24.1(4) . . . . ?
C3 C1 C2 O2 -141.9(4) . . . . ?
C4 C1 C2 O2 90.2(5) . . . . ?
O1 C1 C2 C6 -141.9(4) . . . . ?
C3 C1 C2 C6 100.2(5) . . . . ?
C4 C1 C2 C6 -27.7(6) . . . . ?
O1 C1 C2 C5 89.1(5) . . . . ?
C3 C1 C2 C5 -28.7(6) . . . . ?
C4 C1 C2 C5 -156.6(5) . . . . ?
O3' C7 C8 O4' 22.1(10) . . . . ?
C9' C7 C8 O4' -95.3(12) . . . . ?
C10' C7 C8 O4' 135.8(11) . . . . ?
O4 C7 C8 O3 -22.9(12) . . . . ?
C9 C7 C8 O3 -138.1(12) . . . . ?
C10 C7 C8 O3 92.7(14) . . . . ?
O4 C7 C8 C11 93.8(13) . . . . ?
C9 C7 C8 C11 -21.3(14) . . . . ?
C10 C7 C8 C11 -150.6(15) . . . . ?
O3' C7 C8 C12' -95.6(14) . . . . ?
C9' C7 C8 C12' 147.0(15) . . . . ?
C10' C7 C8 C12' 18.0(15) . . . . ?
O4 C7 C8 C12 -135.4(15) . . . . ?
C9 C7 C8 C12 109.4(16) . . . . ?
C10 C7 C8 C12 -19.8(17) . . . . ?
O3' C7 C8 C11' 136.8(11) . . . . ?
C9' C7 C8 C11' 19.4(13) . . . . ?
C10' C7 C8 C11' -109.6(13) . . . . ?
O1 B1 B2 O3' 174.9(9) . . . . ?
O2 B1 B2 O3' -5.7(8) . . . . ?
O1 B1 B2 O4' -6.1(8) . . . . ?
O2 B1 B2 O4' 173.4(9) . . . . ?
O1 B1 B2 O4 146.4(10) . . . . ?
O2 B1 B2 O4 -34.2(9) . . . . ?
O1 B1 B2 O3 -34.8(9) . . . . ?
O2 B1 B2 O3 144.6(10) . . . . ?
O2 B1 O1 C1 -8.2(6) . . . . ?
B2 B1 O1 C1 171.3(3) . . . . ?
C3 C1 O1 B1 142.7(4) . . . . ?
C4 C1 O1 B1 -98.9(4) . . . . ?
C2 C1 O1 B1 20.1(5) . . . . ?
O1 B1 O2 C2 -8.4(6) . . . . ?
B2 B1 O2 C2 172.1(3) . . . . ?
C6 C2 O2 B1 143.1(4) . . . . ?
C5 C2 O2 B1 -98.5(4) . . . . ?
C1 C2 O2 B1 20.1(5) . . . . ?
O4 B2 O3 C8 -9.1(11) . . . . ?
B1 B2 O3 C8 171.9(5) . . . . ?
C11 C8 O3 B2 -102.2(14) . . . . ?
C12 C8 O3 B2 138.5(19) . . . . ?
C7 C8 O3 B2 19.7(11) . . . . ?
O3 B2 O4 C7 -7.0(11) . . . . ?
B1 B2 O4 C7 172.0(5) . . . . ?
C9 C7 O4 B2 137.8(14) . . . . ?
C10 C7 O4 B2 -102.0(16) . . . . ?
C8 C7 O4 B2 18.6(11) . . . . ?
O4' B2 O3' C7 9.0(10) . . . . ?
B1 B2 O3' C7 -171.8(5) . . . . ?
C9' C7 O3' B2 103.1(14) . . . . ?
C10' C7 O3' B2 -138.3(14) . . . . ?
C8 C7 O3' B2 -19.3(10) . . . . ?
O3' B2 O4' C8 7.0(10) . . . . ?
B1 B2 O4' C8 -172.1(5) . . . . ?
C12' C8 O4' B2 104.3(17) . . . . ?
C11' C8 O4' B2 -136.9(12) . . . . ?
C7 C8 O4' B2 -18.3(10) . . . . ?
O2A C1A C2A O1A -24.4(4) . . . . ?
C3A C1A C2A O1A -141.3(4) . . . . ?
C4A C1A C2A O1A 90.5(5) . . . . ?
O2A C1A C2A C5A 90.5(5) . . . . ?
C3A C1A C2A C5A -26.4(6) . . . . ?
C4A C1A C2A C5A -154.6(5) . . . . ?
O2A C1A C2A C6A -141.6(4) . . . . ?
C3A C1A C2A C6A 101.5(5) . . . . ?
C4A C1A C2A C6A -26.7(6) . . . . ?
O4B C7A C8A O3B 26.3(8) . . . . ?
C9B C7A C8A O3B -91.7(10) . . . . ?
C10B C7A C8A O3B 137.8(10) . . . . ?
O4A C7A C8A O3A -25.9(9) . . . . ?
C10A C7A C8A O3A 93.5(11) . . . . ?
C9A C7A C8A O3A -138.1(9) . . . . ?
O4B C7A C8A C12B -88.8(11) . . . . ?
C9B C7A C8A C12B 153.2(12) . . . . ?
C10B C7A C8A C12B 22.8(13) . . . . ?
O4A C7A C8A C11A 90.9(10) . . . . ?
C10A C7A C8A C11A -149.8(12) . . . . ?
C9A C7A C8A C11A -21.3(10) . . . . ?
O4B C7A C8A C11B 141.4(9) . . . . ?
C9B C7A C8A C11B 23.5(11) . . . . ?
C10B C7A C8A C11B -107.0(11) . . . . ?
O4A C7A C8A C12A -139.5(10) . . . . ?
C10A C7A C8A C12A -20.2(12) . . . . ?
C9A C7A C8A C12A 108.3(10) . . . . ?
O2A B1A B2A O3B -2.5(8) . . . . ?
O1A B1A B2A O3B 178.2(8) . . . . ?
O2A B1A B2A O4A 145.1(8) . . . . ?
O1A B1A B2A O4A -34.2(8) . . . . ?
O2A B1A B2A O4B 178.1(8) . . . . ?
O1A B1A B2A O4B -1.1(7) . . . . ?
O2A B1A B2A O3A -36.0(7) . . . . ?
O1A B1A B2A O3A 144.8(8) . . . . ?
O2A B1A O1A C2A -8.6(5) . . . . ?
B2A B1A O1A C2A 170.7(3) . . . . ?
C5A C2A O1A B1A -99.8(4) . . . . ?
C6A C2A O1A B1A 142.7(4) . . . . ?
C1A C2A O1A B1A 20.5(5) . . . . ?
O1A B1A O2A C1A -8.2(5) . . . . ?
B2A B1A O2A C1A 172.4(3) . . . . ?
C3A C1A O2A B1A 142.3(4) . . . . ?
C4A C1A O2A B1A -99.9(4) . . . . ?
C2A C1A O2A B1A 20.3(5) . . . . ?
O4A B2A O3A C8A -9.8(9) . . . . ?
B1A B2A O3A C8A 171.1(4) . . . . ?
C11A C8A O3A B2A -102.3(9) . . . . ?
C12A C8A O3A B2A 141.6(10) . . . . ?
C7A C8A O3A B2A 22.0(9) . . . . ?
O3A B2A O4A C7A -8.6(9) . . . . ?
B1A B2A O4A C7A 170.5(5) . . . . ?
C10A C7A O4A B2A -101.4(14) . . . . ?
C9A C7A O4A B2A 137.1(11) . . . . ?
C8A C7A O4A B2A 21.4(9) . . . . ?
O4B B2A O3B C8A 9.2(9) . . . . ?
B1A B2A O3B C8A -170.2(5) . . . . ?
C12B C8A O3B B2A 97.5(12) . . . . ?
C11B C8A O3B B2A -139.0(10) . . . . ?
C7A C8A O3B B2A -22.2(9) . . . . ?
O3B B2A O4B C7A 9.6(9) . . . . ?
B1A B2A O4B C7A -171.0(4) . . . . ?
C9B C7A O4B B2A 101.7(11) . . . . ?
C10B C7A O4B B2A -141.4(14) . . . . ?
C8A C7A O4B B2A -22.3(8) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.055

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

data_test_a
_database_code_depnum_ccdc_archive 'CCDC 1529574'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H40 B2 N4 O4), 3(C7 H8)'
_chemical_formula_sum            'C65 H104 B4 N8 O8'
_chemical_formula_weight         1168.80

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

_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                   14.7679(15)
_cell_length_b                   14.7780(15)
_cell_length_c                   17.5940(18)
_cell_angle_alpha                81.575(3)
_cell_angle_beta                 81.666(3)
_cell_angle_gamma                62.615(2)
_cell_volume                     3359.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_F_000             1265
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43221
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.175
_diffrn_reflns_theta_max         26.091
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13307
_reflns_number_gt                11312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.7697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         13307
_refine_ls_number_parameters     787
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35000(10) 0.39980(11) 0.18032(8) 0.0195(3) Uani 1 1 d . . . . .
B1 B 0.26024(17) 0.46944(16) 0.13636(13) 0.0150(4) Uani 1 1 d . . . . .
N1 N 0.13656(12) 0.39355(12) 0.12892(9) 0.0156(3) Uani 1 1 d . . . . .
C1 C 0.16413(14) 0.44262(14) 0.17045(11) 0.0149(4) Uani 1 1 d . . . . .
O2 O 0.24414(10) 0.57303(10) 0.14579(7) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.17968(16) 0.36871(16) 0.05351(11) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.1612 0.3280 0.0281 0.023 Uiso 1 1 calc R U . . .
B2 B 0.10865(17) 0.46831(17) 0.25857(12) 0.0152(4) Uani 1 1 d . . . . .
N2 N 0.28164(13) 0.45586(13) 0.04893(9) 0.0172(4) Uani 1 1 d . . . . .
O3 O 0.15007(10) 0.51995(10) 0.29742(7) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.24697(16) 0.40221(16) 0.01712(11) 0.0198(4) Uani 1 1 d . . . . .
H3 H 0.2714 0.3867 -0.0347 0.024 Uiso 1 1 calc R U . . .
B3 B 0.47529(17) 0.26521(17) 0.63044(13) 0.0164(5) Uani 1 1 d . . . . .
N3 N -0.05239(12) 0.64090(12) 0.21412(9) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.05202(15) 0.36362(15) 0.15640(11) 0.0182(4) Uani 1 1 d . . . . .
H4 H 0.0326 0.3761 0.2121 0.022 Uiso 1 1 calc R U . . .
O4 O 0.12799(10) 0.37112(10) 0.30742(7) 0.0168(3) Uani 1 1 d . . . . .
B4 B 0.47715(16) 0.11527(16) 0.75450(13) 0.0148(4) Uani 1 1 d . . . . .
N4 N -0.10093(12) 0.53832(12) 0.28755(9) 0.0163(3) Uani 1 1 d . . . . .
C5 C -0.04199(16) 0.43228(17) 0.11263(12) 0.0244(5) Uani 1 1 d . . . . .
H01K H -0.0962 0.4113 0.1297 0.037 Uiso 1 1 calc R U . . .
H01L H -0.0237 0.4260 0.0572 0.037 Uiso 1 1 calc R U . . .
H01M H -0.0663 0.5036 0.1229 0.037 Uiso 1 1 calc R U . . .
O5 O 0.57801(10) 0.25199(10) 0.64061(7) 0.0180(3) Uani 1 1 d . . . . .
N5 N 0.40001(12) 0.14107(12) 0.62555(9) 0.0156(3) Uani 1 1 d . . . . .
O6 O 0.40447(10) 0.35511(10) 0.67234(8) 0.0188(3) Uani 1 1 d . . . . .
N6 N 0.46245(13) 0.28441(13) 0.54317(9) 0.0190(4) Uani 1 1 d . . . . .
C6 C 0.08660(17) 0.25061(16) 0.15041(12) 0.0246(5) Uani 1 1 d . . . . .
H01V H 0.0368 0.2300 0.1806 0.037 Uiso 1 1 calc R U . . .
H01W H 0.1538 0.2103 0.1705 0.037 Uiso 1 1 calc R U . . .
H01X H 0.0915 0.2388 0.0963 0.037 Uiso 1 1 calc R U . . .
C7 C 0.35208(16) 0.49078(16) 0.00134(12) 0.0206(4) Uani 1 1 d . . . . .
H7 H 0.3607 0.5380 0.0317 0.025 Uiso 1 1 calc R U . . .
O7 O 0.52995(10) 0.15744(10) 0.79188(7) 0.0168(3) Uani 1 1 d . . . . .
N7 N 0.54968(12) -0.09457(12) 0.78606(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.30824(18) 0.55207(19) -0.07365(12) 0.0311(5) Uani 1 1 d . . . . .
H02H H 0.3510 0.5845 -0.0988 0.047 Uiso 1 1 calc R U . . .
H02I H 0.2383 0.6049 -0.0621 0.047 Uiso 1 1 calc R U . . .
H02J H 0.3073 0.5061 -0.1081 0.047 Uiso 1 1 calc R U . . .
O8 O 0.38182(10) 0.13326(10) 0.80368(7) 0.0162(3) Uani 1 1 d . . . . .
N8 N 0.65012(12) -0.04599(12) 0.71125(9) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.45732(17) 0.40218(17) -0.01333(13) 0.0287(5) Uani 1 1 d . . . . .
H022 H 0.5025 0.4278 -0.0449 0.043 Uiso 1 1 calc R U . . .
H023 H 0.4514 0.3521 -0.0406 0.043 Uiso 1 1 calc R U . . .
H024 H 0.4859 0.3695 0.0360 0.043 Uiso 1 1 calc R U . . .
C24 C 0.37573(16) 0.18241(16) 0.54986(11) 0.0213(4) Uani 1 1 d . . . . .
H24 H 0.3353 0.1629 0.5250 0.026 Uiso 1 1 calc R U . . .
C23 C 0.44955(14) 0.16928(14) 0.66635(10) 0.0136(4) Uani 1 1 d . . . . .
C22 C -0.16509(18) 0.40785(18) 0.31460(14) 0.0296(5) Uani 1 1 d . . . . .
H02E H -0.1651 0.3513 0.3515 0.044 Uiso 1 1 calc R U . . .
H02F H -0.1333 0.3821 0.2644 0.044 Uiso 1 1 calc R U . . .
H02G H -0.2357 0.4603 0.3093 0.044 Uiso 1 1 calc R U . . .
C34 C 0.46059(16) 0.21524(16) 0.85026(11) 0.0207(4) Uani 1 1 d . . . . .
H34A H 0.4212 0.2875 0.8303 0.025 Uiso 1 1 calc R U . . .
H34B H 0.4968 0.2127 0.8943 0.025 Uiso 1 1 calc R U . . .
C33 C 0.46053(16) 0.40214(16) 0.69336(13) 0.0237(5) Uani 1 1 d . . . . .
H01I H 0.4357 0.4252 0.7458 0.028 Uiso 1 1 calc R U . . .
H01J H 0.4533 0.4621 0.6566 0.028 Uiso 1 1 calc R U . . .
C32 C 0.57120(16) 0.32136(16) 0.69118(12) 0.0216(4) Uani 1 1 d . . . . .
H00D H 0.6180 0.3523 0.6715 0.026 Uiso 1 1 calc R U . . .
H00E H 0.5888 0.2864 0.7433 0.026 Uiso 1 1 calc R U . . .
C31 C 0.41106(17) 0.45529(17) 0.47065(14) 0.0317(5) Uani 1 1 d . . . . .
H025 H 0.4384 0.4987 0.4386 0.048 Uiso 1 1 calc R U . . .
H026 H 0.3722 0.4889 0.5169 0.048 Uiso 1 1 calc R U . . .
H027 H 0.3659 0.4443 0.4413 0.048 Uiso 1 1 calc R U . . .
C30 C 0.5672(2) 0.3029(2) 0.42407(16) 0.0532(8) Uani 1 1 d . . . . .
H02K H 0.5999 0.3452 0.3982 0.080 Uiso 1 1 calc R U . . .
H02L H 0.5259 0.2964 0.3883 0.080 Uiso 1 1 calc R U . . .
H02M H 0.6199 0.2349 0.4405 0.080 Uiso 1 1 calc R U . . .
C36 C 0.55818(14) -0.00984(15) 0.75233(11) 0.0148(4) Uani 1 1 d . . . . .
C38 C 0.69793(15) -0.15200(15) 0.71856(12) 0.0200(4) Uani 1 1 d . . . . .
H38 H 0.7630 -0.1950 0.6948 0.024 Uiso 1 1 calc R U . . .
C37 C 0.63533(15) -0.18238(15) 0.76536(12) 0.0206(4) Uani 1 1 d . . . . .
H37 H 0.6474 -0.2509 0.7813 0.025 Uiso 1 1 calc R U . . .
C43 C 0.80281(16) -0.01619(17) 0.68647(13) 0.0258(5) Uani 1 1 d . . . . .
H00A H 0.8305 0.0290 0.6577 0.039 Uiso 1 1 calc R U . . .
H00B H 0.8469 -0.0867 0.6740 0.039 Uiso 1 1 calc R U . . .
H00C H 0.8003 -0.0124 0.7419 0.039 Uiso 1 1 calc R U . . .
C42 C 0.69527(15) 0.01730(15) 0.66436(11) 0.0184(4) Uani 1 1 d . . . . .
H42 H 0.6524 0.0897 0.6768 0.022 Uiso 1 1 calc R U . . .
C44 C 0.69165(17) 0.01376(17) 0.57893(11) 0.0263(5) Uani 1 1 d . . . . .
H01A H 0.7172 0.0597 0.5486 0.039 Uiso 1 1 calc R U . . .
H01B H 0.6209 0.0355 0.5683 0.039 Uiso 1 1 calc R U . . .
H01C H 0.7345 -0.0563 0.5648 0.039 Uiso 1 1 calc R U . . .
C10 C 0.39684(16) 0.45688(16) 0.20005(12) 0.0230(5) Uani 1 1 d . . . . .
H01Y H 0.4560 0.4506 0.1627 0.028 Uiso 1 1 calc R U . . .
H01Z H 0.4207 0.4331 0.2524 0.028 Uiso 1 1 calc R U . . .
C35 C 0.39120(16) 0.16406(15) 0.87395(11) 0.0194(4) Uani 1 1 d . . . . .
H01D H 0.4222 0.1042 0.9119 0.023 Uiso 1 1 calc R U . . .
H01E H 0.3236 0.2126 0.8967 0.023 Uiso 1 1 calc R U . . .
C12 C 0.20698(16) 0.44988(16) 0.35734(11) 0.0209(4) Uani 1 1 d . . . . .
H01N H 0.2022 0.4861 0.4020 0.025 Uiso 1 1 calc R U . . .
H01O H 0.2800 0.4115 0.3388 0.025 Uiso 1 1 calc R U . . .
C39 C 0.46755(15) -0.09865(15) 0.84362(11) 0.0196(4) Uani 1 1 d . . . . .
H39 H 0.4102 -0.0279 0.8461 0.023 Uiso 1 1 calc R U . . .
C13 C 0.15743(16) 0.37917(16) 0.37885(11) 0.0219(4) Uani 1 1 d . . . . .
H00F H 0.2065 0.3114 0.4011 0.026 Uiso 1 1 calc R U . . .
H00G H 0.0971 0.4085 0.4165 0.026 Uiso 1 1 calc R U . . .
C14 C -0.01679(15) 0.54798(15) 0.25459(10) 0.0152(4) Uani 1 1 d . . . . .
C15 C -0.15768(15) 0.68860(16) 0.22139(12) 0.0199(4) Uani 1 1 d . . . . .
H15 H -0.2007 0.7543 0.1983 0.024 Uiso 1 1 calc R U . . .
C16 C -0.18829(16) 0.62505(15) 0.26714(12) 0.0208(4) Uani 1 1 d . . . . .
H16 H -0.2570 0.6373 0.2826 0.025 Uiso 1 1 calc R U . . .
C19 C -0.01899(17) 0.79184(16) 0.19110(12) 0.0244(5) Uani 1 1 d . . . . .
H010 H 0.0271 0.8185 0.1625 0.037 Uiso 1 1 calc R U . . .
H012 H -0.0147 0.7884 0.2466 0.037 Uiso 1 1 calc R U . . .
H014 H -0.0894 0.8373 0.1788 0.037 Uiso 1 1 calc R U . . .
C11 C 0.31261(16) 0.56749(16) 0.19711(12) 0.0228(5) Uani 1 1 d . . . . .
H01S H 0.2769 0.5844 0.2490 0.027 Uiso 1 1 calc R U . . .
H01T H 0.3419 0.6157 0.1779 0.027 Uiso 1 1 calc R U . . .
C18 C 0.00648(17) 0.68614(17) 0.08270(11) 0.0250(5) Uani 1 1 d . . . . .
H015 H 0.0502 0.7149 0.0530 0.038 Uiso 1 1 calc R U . . .
H017 H -0.0644 0.7280 0.0699 0.038 Uiso 1 1 calc R U . . .
H018 H 0.0301 0.6160 0.0700 0.038 Uiso 1 1 calc R U . . .
C17 C 0.01203(15) 0.68560(15) 0.16851(11) 0.0176(4) Uani 1 1 d . . . . .
H17 H 0.0846 0.6412 0.1804 0.021 Uiso 1 1 calc R U . . .
C41 C 0.42685(17) -0.16703(17) 0.82014(13) 0.0267(5) Uani 1 1 d . . . . .
H019 H 0.3714 -0.1674 0.8581 0.040 Uiso 1 1 calc R U . . .
H020 H 0.4822 -0.2368 0.8179 0.040 Uiso 1 1 calc R U . . .
H021 H 0.4007 -0.1410 0.7693 0.040 Uiso 1 1 calc R U . . .
C21 C -0.15165(17) 0.49491(17) 0.42116(11) 0.0268(5) Uani 1 1 d . . . . .
H028 H -0.1519 0.4389 0.4586 0.040 Uiso 1 1 calc R U . . .
H029 H -0.2221 0.5481 0.4164 0.040 Uiso 1 1 calc R U . . .
H02A H -0.1115 0.5240 0.4388 0.040 Uiso 1 1 calc R U . . .
C29 C 0.49877(16) 0.35301(16) 0.49405(12) 0.0228(5) Uani 1 1 d . . . . .
H01U H 0.5413 0.3671 0.5255 0.027 Uiso 1 1 calc R U . . .
C28 C 0.25565(16) 0.09361(17) 0.65111(12) 0.0244(5) Uani 1 1 d . . . . .
H01P H 0.2345 0.0453 0.6831 0.037 Uiso 1 1 calc R U . . .
H01Q H 0.2421 0.0974 0.5975 0.037 Uiso 1 1 calc R U . . .
H01R H 0.2170 0.1615 0.6702 0.037 Uiso 1 1 calc R U . . .
C20 C -0.10455(15) 0.45432(15) 0.34359(11) 0.0200(4) Uani 1 1 d . . . . .
H20 H -0.0330 0.3999 0.3494 0.024 Uiso 1 1 calc R U . . .
C27 C 0.43560(17) -0.03681(16) 0.61278(12) 0.0236(5) Uani 1 1 d . . . . .
H01F H 0.4175 -0.0920 0.6342 0.035 Uiso 1 1 calc R U . . .
H01G H 0.5078 -0.0585 0.6189 0.035 Uiso 1 1 calc R U . . .
H01H H 0.4243 -0.0209 0.5579 0.035 Uiso 1 1 calc R U . . .
C26 C 0.36942(15) 0.05746(14) 0.65510(11) 0.0175(4) Uani 1 1 d . . . . .
H26 H 0.3832 0.0389 0.7107 0.021 Uiso 1 1 calc R U . . .
C25 C 0.40862(16) 0.24909(16) 0.51186(11) 0.0204(4) Uani 1 1 d . . . . .
H25 H 0.3929 0.2725 0.4600 0.024 Uiso 1 1 calc R U . . .
C40 C 0.51006(17) -0.13572(17) 0.92268(11) 0.0261(5) Uani 1 1 d . . . . .
H02B H 0.4560 -0.1372 0.9616 0.039 Uiso 1 1 calc R U . . .
H02C H 0.5343 -0.0890 0.9361 0.039 Uiso 1 1 calc R U . . .
H02D H 0.5671 -0.2047 0.9210 0.039 Uiso 1 1 calc R U . . .
C120 C 0.10869(18) 0.72805(17) 0.40143(13) 0.0331(6) Uani 1 1 d . . . . .
H120 H 0.1373 0.6870 0.3593 0.040 Uiso 1 1 calc R U . . .
C119 C 0.15818(18) 0.77992(18) 0.42150(14) 0.0399(6) Uani 1 1 d . . . . .
H119 H 0.2203 0.7740 0.3933 0.048 Uiso 1 1 calc R U . . .
C118 C 0.11748(19) 0.83989(19) 0.48206(14) 0.0432(6) Uani 1 1 d . . . . .
H118 H 0.1510 0.8760 0.4958 0.052 Uiso 1 1 calc R U . . .
C117 C 0.02803(19) 0.84728(19) 0.52267(13) 0.0414(6) Uani 1 1 d . . . . .
H117 H -0.0002 0.8884 0.5648 0.050 Uiso 1 1 calc R U . . .
C116 C -0.02149(17) 0.79529(16) 0.50273(12) 0.0308(5) Uani 1 1 d . . . . .
H116 H -0.0834 0.8012 0.5313 0.037 Uiso 1 1 calc R U . . .
C115 C 0.01823(15) 0.73494(15) 0.44176(11) 0.0254(4) Uani 1 1 d . . . . .
C114 C -0.03315(17) 0.67503(16) 0.42224(12) 0.0313(5) Uani 1 1 d . . . . .
H11A H -0.1054 0.7068 0.4420 0.047 Uiso 1 1 calc R U . . .
H11B H 0.0005 0.6046 0.4459 0.047 Uiso 1 1 calc R U . . .
H11C H -0.0280 0.6746 0.3661 0.047 Uiso 1 1 calc R U . . .
C113 C 0.22152(15) 0.95899(16) -0.03327(11) 0.0265(4) Uani 1 1 d . . . . .
H113 H 0.1944 0.9499 -0.0758 0.032 Uiso 1 1 calc R U . . .
C112 C 0.23433(15) 1.04553(16) -0.03402(12) 0.0263(4) Uani 1 1 d . . . . .
H112 H 0.2170 1.0954 -0.0771 0.032 Uiso 1 1 calc R U . . .
C111 C 0.27277(15) 1.05997(15) 0.02848(12) 0.0278(5) Uani 1 1 d . . . . .
H111 H 0.2811 1.1200 0.0283 0.033 Uiso 1 1 calc R U . . .
C110 C 0.29865(15) 0.98721(17) 0.09043(12) 0.0306(5) Uani 1 1 d . . . . .
H110 H 0.3252 0.9970 0.1329 0.037 Uiso 1 1 calc R U . . .
C109 C 0.28619(17) 0.89937(18) 0.09123(12) 0.0301(5) Uani 1 1 d . . . . .
H109 H 0.3040 0.8497 0.1344 0.036 Uiso 1 1 calc R U . . .
C108 C 0.24798(15) 0.88369(15) 0.02953(13) 0.0302(5) Uani 1 1 d . . . . .
C107 C 0.2360(2) 0.78850(18) 0.02893(16) 0.0496(7) Uani 1 1 d . . . . .
H10A H 0.2421 0.7528 0.0809 0.074 Uiso 1 1 calc R U . . .
H10B H 0.2895 0.7436 -0.0070 0.074 Uiso 1 1 calc R U . . .
H10C H 0.1686 0.8068 0.0125 0.074 Uiso 1 1 calc R U . . .
C106 C 0.97875(17) 0.01378(17) 0.24709(19) 0.0399(5) Uani 1 1 d . . . . .
H106 H 1.0427 -0.0451 0.2409 0.048 Uiso 1 1 calc R U . . .
C105 C 0.9240(2) 0.0273(2) 0.31837(18) 0.0498(7) Uani 1 1 d . . . . .
H105 H 0.9497 -0.0216 0.3611 0.060 Uiso 1 1 calc R U . . .
C104 C 0.8312(2) 0.1129(2) 0.32689(16) 0.0518(7) Uani 1 1 d . . . . .
H104 H 0.7925 0.1227 0.3757 0.062 Uiso 1 1 calc R U . . .
C103 C 0.79429(19) 0.1847(2) 0.26491(16) 0.0498(7) Uani 1 1 d . . . . .
H103 H 0.7310 0.2442 0.2714 0.060 Uiso 1 1 calc R U . . .
C102 C 0.84895(18) 0.16992(18) 0.19451(15) 0.0393(6) Uani 1 1 d . . . . .
H102 H 0.8224 0.2190 0.1520 0.047 Uiso 1 1 calc R U . . .
C101 C 0.94211(18) 0.08500(18) 0.18371(14) 0.0335(5) Uani 1 1 d . . . . .
C100 C 1.00114(19) 0.0679(2) 0.10686(15) 0.0514(7) Uani 1 1 d . . . . .
H10D H 0.9734 0.1312 0.0726 0.077 Uiso 1 1 calc R U . . .
H10E H 0.9958 0.0136 0.0848 0.077 Uiso 1 1 calc R U . . .
H10F H 1.0732 0.0477 0.1125 0.077 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
O1 C10 1.415(2) . ?
O1 B1 1.491(3) . ?
B1 O2 1.468(2) . ?
B1 N2 1.548(3) . ?
B1 C1 1.653(3) . ?
N1 C1 1.318(2) . ?
N1 C2 1.408(2) . ?
N1 C4 1.503(2) . ?
C1 B2 1.654(3) . ?
O2 C11 1.418(2) . ?
C2 C3 1.348(3) . ?
C2 H2 0.9500 . ?
B2 O3 1.459(2) . ?
B2 O4 1.488(2) . ?
B2 C14 1.682(3) . ?
N2 C3 1.338(2) . ?
N2 C7 1.471(2) . ?
O3 C12 1.423(2) . ?
C3 H3 0.9500 . ?
B3 O5 1.472(2) . ?
B3 O6 1.479(3) . ?
B3 N6 1.543(3) . ?
B3 C23 1.648(3) . ?
N3 C14 1.352(2) . ?
N3 C15 1.375(3) . ?
N3 C17 1.479(2) . ?
C4 C6 1.521(3) . ?
C4 C5 1.528(3) . ?
C4 H4 1.0000 . ?
O4 C13 1.426(2) . ?
B4 O7 1.464(2) . ?
B4 O8 1.474(2) . ?
B4 C23 1.652(3) . ?
B4 C36 1.680(3) . ?
N4 C14 1.353(2) . ?
N4 C16 1.384(3) . ?
N4 C20 1.484(2) . ?
C5 H01K 0.9800 . ?
C5 H01L 0.9800 . ?
C5 H01M 0.9800 . ?
O5 C32 1.414(2) . ?
N5 C23 1.321(2) . ?
N5 C24 1.405(2) . ?
N5 C26 1.503(2) . ?
O6 C33 1.414(2) . ?
N6 C25 1.342(2) . ?
N6 C29 1.474(2) . ?
C6 H01V 0.9800 . ?
C6 H01W 0.9800 . ?
C6 H01X 0.9800 . ?
C7 C9 1.519(3) . ?
C7 C8 1.529(3) . ?
C7 H7 1.0000 . ?
O7 C34 1.408(2) . ?
N7 C36 1.357(2) . ?
N7 C37 1.383(3) . ?
N7 C39 1.481(2) . ?
C8 H02H 0.9800 . ?
C8 H02I 0.9800 . ?
C8 H02J 0.9800 . ?
O8 C35 1.424(2) . ?
N8 C36 1.346(2) . ?
N8 C38 1.385(2) . ?
N8 C42 1.479(2) . ?
C9 H022 0.9800 . ?
C9 H023 0.9800 . ?
C9 H024 0.9800 . ?
C24 C25 1.344(3) . ?
C24 H24 0.9500 . ?
C22 C20 1.527(3) . ?
C22 H02E 0.9800 . ?
C22 H02F 0.9800 . ?
C22 H02G 0.9800 . ?
C34 C35 1.514(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C33 C32 1.516(3) . ?
C33 H01I 0.9900 . ?
C33 H01J 0.9900 . ?
C32 H00D 0.9900 . ?
C32 H00E 0.9900 . ?
C31 C29 1.518(3) . ?
C31 H025 0.9800 . ?
C31 H026 0.9800 . ?
C31 H027 0.9800 . ?
C30 C29 1.517(3) . ?
C30 H02K 0.9800 . ?
C30 H02L 0.9800 . ?
C30 H02M 0.9800 . ?
C38 C37 1.337(3) . ?
C38 H38 0.9500 . ?
C37 H37 0.9500 . ?
C43 C42 1.523(3) . ?
C43 H00A 0.9800 . ?
C43 H00B 0.9800 . ?
C43 H00C 0.9800 . ?
C42 C44 1.521(3) . ?
C42 H42 1.0000 . ?
C44 H01A 0.9800 . ?
C44 H01B 0.9800 . ?
C44 H01C 0.9800 . ?
C10 C11 1.531(3) . ?
C10 H01Y 0.9900 . ?
C10 H01Z 0.9900 . ?
C35 H01D 0.9900 . ?
C35 H01E 0.9900 . ?
C12 C13 1.509(3) . ?
C12 H01N 0.9900 . ?
C12 H01O 0.9900 . ?
C39 C41 1.519(3) . ?
C39 C40 1.531(3) . ?
C39 H39 1.0000 . ?
C13 H00F 0.9900 . ?
C13 H00G 0.9900 . ?
C15 C16 1.341(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C19 C17 1.517(3) . ?
C19 H010 0.9800 . ?
C19 H012 0.9800 . ?
C19 H014 0.9800 . ?
C11 H01S 0.9900 . ?
C11 H01T 0.9900 . ?
C18 C17 1.522(3) . ?
C18 H015 0.9800 . ?
C18 H017 0.9800 . ?
C18 H018 0.9800 . ?
C17 H17 1.0000 . ?
C41 H019 0.9800 . ?
C41 H020 0.9800 . ?
C41 H021 0.9800 . ?
C21 C20 1.512(3) . ?
C21 H028 0.9800 . ?
C21 H029 0.9800 . ?
C21 H02A 0.9800 . ?
C29 H01U 1.0000 . ?
C28 C26 1.520(3) . ?
C28 H01P 0.9800 . ?
C28 H01Q 0.9800 . ?
C28 H01R 0.9800 . ?
C20 H20 1.0000 . ?
C27 C26 1.514(3) . ?
C27 H01F 0.9800 . ?
C27 H01G 0.9800 . ?
C27 H01H 0.9800 . ?
C26 H26 1.0000 . ?
C25 H25 0.9500 . ?
C40 H02B 0.9800 . ?
C40 H02C 0.9800 . ?
C40 H02D 0.9800 . ?
C120 C119 1.384(3) . ?
C120 C115 1.386(3) . ?
C120 H120 0.9500 . ?
C119 C118 1.372(3) . ?
C119 H119 0.9500 . ?
C118 C117 1.373(3) . ?
C118 H118 0.9500 . ?
C117 C116 1.385(3) . ?
C117 H117 0.9500 . ?
C116 C115 1.381(3) . ?
C116 H116 0.9500 . ?
C115 C114 1.503(3) . ?
C114 H11A 0.9800 . ?
C114 H11B 0.9800 . ?
C114 H11C 0.9800 . ?
C113 C112 1.374(3) . ?
C113 C108 1.406(3) . ?
C113 H113 0.9500 . ?
C112 C111 1.392(3) . ?
C112 H112 0.9500 . ?
C111 C110 1.375(3) . ?
C111 H111 0.9500 . ?
C110 C109 1.390(3) . ?
C110 H110 0.9500 . ?
C109 C108 1.386(3) . ?
C109 H109 0.9500 . ?
C108 C107 1.498(3) . ?
C107 H10A 0.9800 . ?
C107 H10B 0.9800 . ?
C107 H10C 0.9800 . ?
C106 C105 1.378(4) . ?
C106 C101 1.397(4) . ?
C106 H106 0.9500 . ?
C105 C104 1.378(4) . ?
C105 H105 0.9500 . ?
C104 C103 1.383(4) . ?
C104 H104 0.9500 . ?
C103 C102 1.364(4) . ?
C103 H103 0.9500 . ?
C102 C101 1.382(3) . ?
C102 H102 0.9500 . ?
C101 C100 1.486(3) . ?
C100 H10D 0.9800 . ?
C100 H10E 0.9800 . ?
C100 H10F 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
C10 O1 B1 109.13(15) . . ?
O2 B1 O1 104.90(15) . . ?
O2 B1 N2 107.47(15) . . ?
O1 B1 N2 112.60(16) . . ?
O2 B1 C1 115.79(16) . . ?
O1 B1 C1 107.92(15) . . ?
N2 B1 C1 108.27(15) . . ?
C1 N1 C2 123.46(15) . . ?
C1 N1 C4 122.85(15) . . ?
C2 N1 C4 113.62(14) . . ?
N1 C1 B1 119.35(16) . . ?
N1 C1 B2 119.75(15) . . ?
B1 C1 B2 120.72(15) . . ?
C11 O2 B1 109.60(16) . . ?
C3 C2 N1 120.58(18) . . ?
C3 C2 H2 119.7 . . ?
N1 C2 H2 119.7 . . ?
O3 B2 O4 105.52(15) . . ?
O3 B2 C1 112.80(14) . . ?
O4 B2 C1 109.65(16) . . ?
O3 B2 C14 106.12(16) . . ?
O4 B2 C14 112.86(14) . . ?
C1 B2 C14 109.84(16) . . ?
C3 N2 C7 118.57(16) . . ?
C3 N2 B1 121.22(15) . . ?
C7 N2 B1 119.75(15) . . ?
C12 O3 B2 107.92(14) . . ?
N2 C3 C2 124.47(18) . . ?
N2 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
O5 B3 O6 104.48(15) . . ?
O5 B3 N6 107.79(15) . . ?
O6 B3 N6 112.27(17) . . ?
O5 B3 C23 116.10(17) . . ?
O6 B3 C23 107.59(15) . . ?
N6 B3 C23 108.66(15) . . ?
C14 N3 C15 110.29(15) . . ?
C14 N3 C17 125.19(16) . . ?
C15 N3 C17 124.51(16) . . ?
N1 C4 C6 111.80(16) . . ?
N1 C4 C5 109.75(15) . . ?
C6 C4 C5 112.27(16) . . ?
N1 C4 H4 107.6 . . ?
C6 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C13 O4 B2 106.95(14) . . ?
O7 B4 O8 106.23(15) . . ?
O7 B4 C23 113.11(14) . . ?
O8 B4 C23 109.59(16) . . ?
O7 B4 C36 104.98(15) . . ?
O8 B4 C36 112.40(14) . . ?
C23 B4 C36 110.43(16) . . ?
C14 N4 C16 109.88(16) . . ?
C14 N4 C20 127.42(17) . . ?
C16 N4 C20 122.45(15) . . ?
C4 C5 H01K 109.5 . . ?
C4 C5 H01L 109.5 . . ?
H01K C5 H01L 109.5 . . ?
C4 C5 H01M 109.5 . . ?
H01K C5 H01M 109.5 . . ?
H01L C5 H01M 109.5 . . ?
C32 O5 B3 110.39(15) . . ?
C23 N5 C24 123.43(15) . . ?
C23 N5 C26 122.45(15) . . ?
C24 N5 C26 114.05(14) . . ?
C33 O6 B3 109.02(15) . . ?
C25 N6 C29 118.32(16) . . ?
C25 N6 B3 121.33(15) . . ?
C29 N6 B3 119.93(15) . . ?
C4 C6 H01V 109.5 . . ?
C4 C6 H01W 109.5 . . ?
H01V C6 H01W 109.5 . . ?
C4 C6 H01X 109.5 . . ?
H01V C6 H01X 109.5 . . ?
H01W C6 H01X 109.5 . . ?
N2 C7 C9 111.34(16) . . ?
N2 C7 C8 112.12(17) . . ?
C9 C7 C8 111.95(18) . . ?
N2 C7 H7 107.0 . . ?
C9 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C34 O7 B4 107.40(14) . . ?
C36 N7 C37 110.78(16) . . ?
C36 N7 C39 127.28(16) . . ?
C37 N7 C39 121.69(16) . . ?
C7 C8 H02H 109.5 . . ?
C7 C8 H02I 109.5 . . ?
H02H C8 H02I 109.5 . . ?
C7 C8 H02J 109.5 . . ?
H02H C8 H02J 109.5 . . ?
H02I C8 H02J 109.5 . . ?
C35 O8 B4 106.29(14) . . ?
C36 N8 C38 110.66(15) . . ?
C36 N8 C42 125.46(16) . . ?
C38 N8 C42 123.88(16) . . ?
C7 C9 H022 109.5 . . ?
C7 C9 H023 109.5 . . ?
H022 C9 H023 109.5 . . ?
C7 C9 H024 109.5 . . ?
H022 C9 H024 109.5 . . ?
H023 C9 H024 109.5 . . ?
C25 C24 N5 121.29(18) . . ?
C25 C24 H24 119.4 . . ?
N5 C24 H24 119.4 . . ?
N5 C23 B3 118.79(16) . . ?
N5 C23 B4 120.45(15) . . ?
B3 C23 B4 120.60(15) . . ?
C20 C22 H02E 109.5 . . ?
C20 C22 H02F 109.5 . . ?
H02E C22 H02F 109.5 . . ?
C20 C22 H02G 109.5 . . ?
H02E C22 H02G 109.5 . . ?
H02F C22 H02G 109.5 . . ?
O7 C34 C35 103.83(15) . . ?
O7 C34 H34A 111.0 . . ?
C35 C34 H34A 111.0 . . ?
O7 C34 H34B 111.0 . . ?
C35 C34 H34B 111.0 . . ?
H34A C34 H34B 109.0 . . ?
O6 C33 C32 106.02(16) . . ?
O6 C33 H01I 110.5 . . ?
C32 C33 H01I 110.5 . . ?
O6 C33 H01J 110.5 . . ?
C32 C33 H01J 110.5 . . ?
H01I C33 H01J 108.7 . . ?
O5 C32 C33 104.77(16) . . ?
O5 C32 H00D 110.8 . . ?
C33 C32 H00D 110.8 . . ?
O5 C32 H00E 110.8 . . ?
C33 C32 H00E 110.8 . . ?
H00D C32 H00E 108.9 . . ?
C29 C31 H025 109.5 . . ?
C29 C31 H026 109.5 . . ?
H025 C31 H026 109.5 . . ?
C29 C31 H027 109.5 . . ?
H025 C31 H027 109.5 . . ?
H026 C31 H027 109.5 . . ?
C29 C30 H02K 109.5 . . ?
C29 C30 H02L 109.5 . . ?
H02K C30 H02L 109.5 . . ?
C29 C30 H02M 109.5 . . ?
H02K C30 H02M 109.5 . . ?
H02L C30 H02M 109.5 . . ?
N8 C36 N7 104.76(16) . . ?
N8 C36 B4 123.76(15) . . ?
N7 C36 B4 131.45(16) . . ?
C37 C38 N8 107.16(18) . . ?
C37 C38 H38 126.4 . . ?
N8 C38 H38 126.4 . . ?
C38 C37 N7 106.63(17) . . ?
C38 C37 H37 126.7 . . ?
N7 C37 H37 126.7 . . ?
C42 C43 H00A 109.5 . . ?
C42 C43 H00B 109.5 . . ?
H00A C43 H00B 109.5 . . ?
C42 C43 H00C 109.5 . . ?
H00A C43 H00C 109.5 . . ?
H00B C43 H00C 109.5 . . ?
N8 C42 C44 110.22(15) . . ?
N8 C42 C43 109.93(16) . . ?
C44 C42 C43 113.21(17) . . ?
N8 C42 H42 107.8 . . ?
C44 C42 H42 107.8 . . ?
C43 C42 H42 107.8 . . ?
C42 C44 H01A 109.5 . . ?
C42 C44 H01B 109.5 . . ?
H01A C44 H01B 109.5 . . ?
C42 C44 H01C 109.5 . . ?
H01A C44 H01C 109.5 . . ?
H01B C44 H01C 109.5 . . ?
O1 C10 C11 104.61(16) . . ?
O1 C10 H01Y 110.8 . . ?
C11 C10 H01Y 110.8 . . ?
O1 C10 H01Z 110.8 . . ?
C11 C10 H01Z 110.8 . . ?
H01Y C10 H01Z 108.9 . . ?
O8 C35 C34 103.90(14) . . ?
O8 C35 H01D 111.0 . . ?
C34 C35 H01D 111.0 . . ?
O8 C35 H01E 111.0 . . ?
C34 C35 H01E 111.0 . . ?
H01D C35 H01E 109.0 . . ?
O3 C12 C13 104.18(15) . . ?
O3 C12 H01N 110.9 . . ?
C13 C12 H01N 110.9 . . ?
O3 C12 H01O 110.9 . . ?
C13 C12 H01O 110.9 . . ?
H01N C12 H01O 108.9 . . ?
N7 C39 C41 110.56(16) . . ?
N7 C39 C40 108.59(16) . . ?
C41 C39 C40 111.99(17) . . ?
N7 C39 H39 108.5 . . ?
C41 C39 H39 108.5 . . ?
C40 C39 H39 108.5 . . ?
O4 C13 C12 103.74(15) . . ?
O4 C13 H00F 111.0 . . ?
C12 C13 H00F 111.0 . . ?
O4 C13 H00G 111.0 . . ?
C12 C13 H00G 111.0 . . ?
H00F C13 H00G 109.0 . . ?
N3 C14 N4 105.55(16) . . ?
N3 C14 B2 123.21(15) . . ?
N4 C14 B2 131.23(16) . . ?
C16 C15 N3 107.18(18) . . ?
C16 C15 H15 126.4 . . ?
N3 C15 H15 126.4 . . ?
C15 C16 N4 107.09(17) . . ?
C15 C16 H16 126.5 . . ?
N4 C16 H16 126.5 . . ?
C17 C19 H010 109.5 . . ?
C17 C19 H012 109.5 . . ?
H010 C19 H012 109.5 . . ?
C17 C19 H014 109.5 . . ?
H010 C19 H014 109.5 . . ?
H012 C19 H014 109.5 . . ?
O2 C11 C10 105.63(15) . . ?
O2 C11 H01S 110.6 . . ?
C10 C11 H01S 110.6 . . ?
O2 C11 H01T 110.6 . . ?
C10 C11 H01T 110.6 . . ?
H01S C11 H01T 108.7 . . ?
C17 C18 H015 109.5 . . ?
C17 C18 H017 109.5 . . ?
H015 C18 H017 109.5 . . ?
C17 C18 H018 109.5 . . ?
H015 C18 H018 109.5 . . ?
H017 C18 H018 109.5 . . ?
N3 C17 C19 110.68(16) . . ?
N3 C17 C18 110.05(15) . . ?
C19 C17 C18 111.92(17) . . ?
N3 C17 H17 108.0 . . ?
C19 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
C39 C41 H019 109.5 . . ?
C39 C41 H020 109.5 . . ?
H019 C41 H020 109.5 . . ?
C39 C41 H021 109.5 . . ?
H019 C41 H021 109.5 . . ?
H020 C41 H021 109.5 . . ?
C20 C21 H028 109.5 . . ?
C20 C21 H029 109.5 . . ?
H028 C21 H029 109.5 . . ?
C20 C21 H02A 109.5 . . ?
H028 C21 H02A 109.5 . . ?
H029 C21 H02A 109.5 . . ?
N6 C29 C30 111.86(17) . . ?
N6 C29 C31 112.07(17) . . ?
C30 C29 C31 111.2(2) . . ?
N6 C29 H01U 107.1 . . ?
C30 C29 H01U 107.1 . . ?
C31 C29 H01U 107.1 . . ?
C26 C28 H01P 109.5 . . ?
C26 C28 H01Q 109.5 . . ?
H01P C28 H01Q 109.5 . . ?
C26 C28 H01R 109.5 . . ?
H01P C28 H01R 109.5 . . ?
H01Q C28 H01R 109.5 . . ?
N4 C20 C21 109.50(16) . . ?
N4 C20 C22 110.53(17) . . ?
C21 C20 C22 110.82(17) . . ?
N4 C20 H20 108.6 . . ?
C21 C20 H20 108.6 . . ?
C22 C20 H20 108.6 . . ?
C26 C27 H01F 109.5 . . ?
C26 C27 H01G 109.5 . . ?
H01F C27 H01G 109.5 . . ?
C26 C27 H01H 109.5 . . ?
H01F C27 H01H 109.5 . . ?
H01G C27 H01H 109.5 . . ?
N5 C26 C27 109.99(15) . . ?
N5 C26 C28 111.52(16) . . ?
C27 C26 C28 112.75(16) . . ?
N5 C26 H26 107.4 . . ?
C27 C26 H26 107.4 . . ?
C28 C26 H26 107.4 . . ?
N6 C25 C24 123.65(19) . . ?
N6 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?
C39 C40 H02B 109.5 . . ?
C39 C40 H02C 109.5 . . ?
H02B C40 H02C 109.5 . . ?
C39 C40 H02D 109.5 . . ?
H02B C40 H02D 109.5 . . ?
H02C C40 H02D 109.5 . . ?
C119 C120 C115 121.2(2) . . ?
C119 C120 H120 119.4 . . ?
C115 C120 H120 119.4 . . ?
C118 C119 C120 120.0(2) . . ?
C118 C119 H119 120.0 . . ?
C120 C119 H119 120.0 . . ?
C119 C118 C117 119.5(2) . . ?
C119 C118 H118 120.3 . . ?
C117 C118 H118 120.3 . . ?
C118 C117 C116 120.6(2) . . ?
C118 C117 H117 119.7 . . ?
C116 C117 H117 119.7 . . ?
C115 C116 C117 120.7(2) . . ?
C115 C116 H116 119.7 . . ?
C117 C116 H116 119.7 . . ?
C116 C115 C120 118.09(19) . . ?
C116 C115 C114 120.64(18) . . ?
C120 C115 C114 121.22(19) . . ?
C115 C114 H11A 109.5 . . ?
C115 C114 H11B 109.5 . . ?
H11A C114 H11B 109.5 . . ?
C115 C114 H11C 109.5 . . ?
H11A C114 H11C 109.5 . . ?
H11B C114 H11C 109.5 . . ?
C112 C113 C108 120.89(19) . . ?
C112 C113 H113 119.6 . . ?
C108 C113 H113 119.6 . . ?
C113 C112 C111 119.88(19) . . ?
C113 C112 H112 120.1 . . ?
C111 C112 H112 120.1 . . ?
C110 C111 C112 119.91(19) . . ?
C110 C111 H111 120.0 . . ?
C112 C111 H111 120.0 . . ?
C111 C110 C109 120.4(2) . . ?
C111 C110 H110 119.8 . . ?
C109 C110 H110 119.8 . . ?
C108 C109 C110 120.5(2) . . ?
C108 C109 H109 119.7 . . ?
C110 C109 H109 119.7 . . ?
C109 C108 C113 118.41(19) . . ?
C109 C108 C107 121.2(2) . . ?
C113 C108 C107 120.4(2) . . ?
C108 C107 H10A 109.5 . . ?
C108 C107 H10B 109.5 . . ?
H10A C107 H10B 109.5 . . ?
C108 C107 H10C 109.5 . . ?
H10A C107 H10C 109.5 . . ?
H10B C107 H10C 109.5 . . ?
C105 C106 C101 121.3(2) . . ?
C105 C106 H106 119.4 . . ?
C101 C106 H106 119.4 . . ?
C106 C105 C104 119.1(3) . . ?
C106 C105 H105 120.5 . . ?
C104 C105 H105 120.5 . . ?
C105 C104 C103 120.4(3) . . ?
C105 C104 H104 119.8 . . ?
C103 C104 H104 119.8 . . ?
C102 C103 C104 119.9(2) . . ?
C102 C103 H103 120.1 . . ?
C104 C103 H103 120.1 . . ?
C103 C102 C101 121.3(3) . . ?
C103 C102 H102 119.3 . . ?
C101 C102 H102 119.3 . . ?
C102 C101 C106 118.0(2) . . ?
C102 C101 C100 121.5(2) . . ?
C106 C101 C100 120.5(2) . . ?
C101 C100 H10D 109.5 . . ?
C101 C100 H10E 109.5 . . ?
H10D C100 H10E 109.5 . . ?
C101 C100 H10F 109.5 . . ?
H10D C100 H10F 109.5 . . ?
H10E C100 H10F 109.5 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039

_shelxl_version_number           2014/6

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

data_ae147_a
_database_code_depnum_ccdc_archive 'CCDC 1529575'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H32 B2 N2 O4 '
_chemical_formula_sum            'C25 H32 B2 N2 O4'
_chemical_formula_weight         446.14

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

_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                   8.3809(3)
_cell_length_b                   18.6842(6)
_cell_length_c                   15.0663(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.245(2)
_cell_angle_gamma                90
_cell_volume                     2328.59(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6658
_cell_measurement_theta_min      2.462
_cell_measurement_theta_max      26.047

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6094
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22541
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         26.051
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4597
_reflns_number_gt                3677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0504P)²+1.1973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4597
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.48537(18) 0.26534(8) 0.62973(10) 0.0165(3) Uani 1 1 d . . . . .
B1 B 0.6286(2) 0.20338(10) 0.49227(12) 0.0192(4) Uani 1 1 d . . . . .
O1 O 0.78481(14) 0.22817(6) 0.49706(8) 0.0256(3) Uani 1 1 d . . . . .
C2 C 0.5260(2) 0.23777(9) 0.77759(10) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.5544 0.2116 0.8319 0.025 Uiso 1 1 calc R U . . .
B2 B 0.4712(2) 0.25591(9) 0.51788(12) 0.0180(4) Uani 1 1 d . . . . .
O2 O 0.61302(13) 0.13535(6) 0.45642(7) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.4673(2) 0.30457(9) 0.76915(10) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.4463 0.3349 0.8165 0.026 Uiso 1 1 calc R U . . .
O3 O 0.47441(13) 0.32630(6) 0.47362(7) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.60190(19) 0.14517(8) 0.67377(10) 0.0160(3) Uani 1 1 d . . . . .
O4 O 0.30758(14) 0.22639(6) 0.48584(8) 0.0286(3) Uani 1 1 d . . . . .
C5 C 0.77002(19) 0.13761(8) 0.68556(10) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.8308(2) 0.07121(9) 0.66788(11) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.9446 0.0647 0.6761 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5647(2) 0.02331(8) 0.62981(10) 0.0199(3) Uani 1 1 d . . . . .
H8 H 0.4952 -0.0158 0.6107 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7311(2) 0.01366(8) 0.63852(10) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.49722(19) 0.08847(8) 0.64817(10) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.8800(2) 0.19964(9) 0.71488(12) 0.0261(4) Uani 1 1 d . . . . .
H10A H 0.9928 0.1839 0.7209 0.039 Uiso 1 1 calc R U . . .
H10B H 0.8584 0.2176 0.7729 0.039 Uiso 1 1 calc R U . . .
H10C H 0.8606 0.2379 0.6699 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8019(2) -0.05688(9) 0.61647(13) 0.0292(4) Uani 1 1 d . . . . .
H11A H 0.7155 -0.0882 0.5870 0.044 Uiso 1 1 calc R U . . .
H11B H 0.8556 -0.0795 0.6720 0.044 Uiso 1 1 calc R U . . .
H11C H 0.8809 -0.0489 0.5761 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3166(2) 0.09787(9) 0.63949(12) 0.0249(4) Uani 1 1 d . . . . .
H12A H 0.2795 0.1316 0.5907 0.037 Uiso 1 1 calc R U . . .
H12B H 0.2898 0.1166 0.6960 0.037 Uiso 1 1 calc R U . . .
H12C H 0.2633 0.0516 0.6261 0.037 Uiso 1 1 calc R U . . .
C13 C 0.37326(19) 0.38894(8) 0.64676(10) 0.0166(3) Uani 1 1 d . . . . .
C14 C 0.20622(19) 0.39689(8) 0.63999(10) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.14120(19) 0.46400(9) 0.61736(10) 0.0196(3) Uani 1 1 d . . . . .
H15 H 0.0280 0.4707 0.6137 0.024 Uiso 1 1 calc R U . . .
C16 C 0.2359(2) 0.52162(8) 0.59989(10) 0.0186(3) Uani 1 1 d . . . . .
C17 C 0.4019(2) 0.51054(8) 0.60549(10) 0.0186(3) Uani 1 1 d . . . . .
H17 H 0.4679 0.5491 0.5921 0.022 Uiso 1 1 calc R U . . .
C18 C 0.47357(19) 0.44505(8) 0.63002(10) 0.0183(3) Uani 1 1 d . . . . .
C19 C 0.1001(2) 0.33485(9) 0.65601(12) 0.0253(4) Uani 1 1 d . . . . .
H19A H -0.0136 0.3480 0.6374 0.038 Uiso 1 1 calc R U . . .
H19B H 0.1187 0.3226 0.7201 0.038 Uiso 1 1 calc R U . . .
H19C H 0.1260 0.2935 0.6209 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1623(2) 0.59394(9) 0.57730(11) 0.0232(4) Uani 1 1 d . . . . .
H20A H 0.2425 0.6253 0.5566 0.035 Uiso 1 1 calc R U . . .
H20B H 0.1278 0.6147 0.6309 0.035 Uiso 1 1 calc R U . . .
H20C H 0.0685 0.5890 0.5296 0.035 Uiso 1 1 calc R U . . .
C21 C 0.6539(2) 0.43487(9) 0.63812(12) 0.0244(4) Uani 1 1 d . . . . .
H21A H 0.6767 0.3983 0.5953 0.037 Uiso 1 1 calc R U . . .
H21B H 0.6979 0.4196 0.6994 0.037 Uiso 1 1 calc R U . . .
H21C H 0.7043 0.4802 0.6249 0.037 Uiso 1 1 calc R U . . .
C22 C 0.8826(2) 0.17277(10) 0.46706(14) 0.0334(4) Uani 1 1 d . . . . .
H22A H 0.9662 0.1564 0.5169 0.040 Uiso 1 1 calc R U . . .
H22B H 0.9365 0.1902 0.4174 0.040 Uiso 1 1 calc R U . . .
C23 C 0.7663(2) 0.11262(9) 0.43517(11) 0.0246(4) Uani 1 1 d . . . . .
H23A H 0.7595 0.1051 0.3696 0.030 Uiso 1 1 calc R U . . .
H23B H 0.8016 0.0674 0.4667 0.030 Uiso 1 1 calc R U . . .
N28 N 0.53722(15) 0.21438(7) 0.69171(8) 0.0166(3) Uani 1 1 d . . . . .
C25 C 0.2173(2) 0.27587(9) 0.43002(12) 0.0266(4) Uani 1 1 d . . . . .
H25A H 0.1135 0.2853 0.4513 0.032 Uiso 1 1 calc R U . . .
H25B H 0.1934 0.2571 0.3679 0.032 Uiso 1 1 calc R U . . .
C24 C 0.31540(19) 0.34431(9) 0.43202(11) 0.0202(3) Uani 1 1 d . . . . .
H24A H 0.3158 0.3623 0.3702 0.024 Uiso 1 1 calc R U . . .
H24B H 0.2695 0.3818 0.4669 0.024 Uiso 1 1 calc R U . . .
N29 N 0.44307(15) 0.32090(7) 0.67861(8) 0.0172(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N29 1.353(2) . ?
C1 N28 1.3554(19) . ?
C1 B2 1.679(2) . ?
B1 O2 1.379(2) . ?
B1 O1 1.380(2) . ?
B1 B2 1.737(3) . ?
O1 C22 1.437(2) . ?
C2 C3 1.340(2) . ?
C2 N28 1.383(2) . ?
C2 H2 0.9500 . ?
B2 O3 1.477(2) . ?
B2 O4 1.485(2) . ?
O2 C23 1.437(2) . ?
C3 N29 1.381(2) . ?
C3 H3 0.9500 . ?
O3 C24 1.4190(18) . ?
C4 C9 1.390(2) . ?
C4 C5 1.399(2) . ?
C4 N28 1.4442(19) . ?
O4 C25 1.389(2) . ?
C5 C6 1.383(2) . ?
C5 C10 1.502(2) . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.389(2) . ?
C8 C7 1.391(2) . ?
C8 H8 0.9500 . ?
C7 C11 1.504(2) . ?
C9 C12 1.509(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.392(2) . ?
C13 C14 1.395(2) . ?
C13 N29 1.4486(19) . ?
C14 C15 1.388(2) . ?
C14 C19 1.504(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(2) . ?
C16 C20 1.502(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C21 1.509(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.514(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 C24 1.518(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
N29 C1 N28 104.31(13) . . ?
N29 C1 B2 130.11(13) . . ?
N28 C1 B2 125.51(13) . . ?
O2 B1 O1 111.06(15) . . ?
O2 B1 B2 125.47(15) . . ?
O1 B1 B2 123.16(14) . . ?
B1 O1 C22 109.02(13) . . ?
C3 C2 N28 106.54(14) . . ?
C3 C2 H2 126.7 . . ?
N28 C2 H2 126.7 . . ?
O3 B2 O4 105.48(13) . . ?
O3 B2 C1 110.87(12) . . ?
O4 B2 C1 106.14(13) . . ?
O3 B2 B1 109.47(13) . . ?
O4 B2 B1 114.37(13) . . ?
C1 B2 B1 110.39(12) . . ?
B1 O2 C23 109.13(13) . . ?
C2 C3 N29 107.03(14) . . ?
C2 C3 H3 126.5 . . ?
N29 C3 H3 126.5 . . ?
C24 O3 B2 109.06(12) . . ?
C9 C4 C5 122.42(14) . . ?
C9 C4 N28 119.68(14) . . ?
C5 C4 N28 117.87(14) . . ?
C25 O4 B2 109.54(12) . . ?
C6 C5 C4 117.43(14) . . ?
C6 C5 C10 121.42(15) . . ?
C4 C5 C10 121.14(14) . . ?
C5 C6 C7 122.30(15) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C9 C8 C7 121.94(15) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C6 C7 C8 118.16(15) . . ?
C6 C7 C11 120.65(15) . . ?
C8 C7 C11 121.19(15) . . ?
C8 C9 C4 117.67(15) . . ?
C8 C9 C12 121.32(15) . . ?
C4 C9 C12 121.01(14) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.33(14) . . ?
C18 C13 N29 119.83(14) . . ?
C14 C13 N29 117.69(13) . . ?
C15 C14 C13 117.64(14) . . ?
C15 C14 C19 121.12(14) . . ?
C13 C14 C19 121.24(14) . . ?
C16 C15 C14 122.27(15) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 117.93(14) . . ?
C15 C16 C20 120.99(15) . . ?
C17 C16 C20 121.08(14) . . ?
C18 C17 C16 122.13(15) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C13 117.67(14) . . ?
C17 C18 C21 121.22(14) . . ?
C13 C18 C21 121.11(14) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 C23 105.31(14) . . ?
O1 C22 H22A 110.7 . . ?
C23 C22 H22A 110.7 . . ?
O1 C22 H22B 110.7 . . ?
C23 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
O2 C23 C22 105.23(13) . . ?
O2 C23 H23A 110.7 . . ?
C22 C23 H23A 110.7 . . ?
O2 C23 H23B 110.7 . . ?
C22 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
C1 N28 C2 111.11(13) . . ?
C1 N28 C4 126.04(13) . . ?
C2 N28 C4 122.81(13) . . ?
O4 C25 C24 107.92(13) . . ?
O4 C25 H25A 110.1 . . ?
C24 C25 H25A 110.1 . . ?
O4 C25 H25B 110.1 . . ?
C24 C25 H25B 110.1 . . ?
H25A C25 H25B 108.4 . . ?
O3 C24 C25 106.04(12) . . ?
O3 C24 H24A 110.5 . . ?
C25 C24 H24A 110.5 . . ?
O3 C24 H24B 110.5 . . ?
C25 C24 H24B 110.5 . . ?
H24A C24 H24B 108.7 . . ?
C1 N29 C3 111.01(13) . . ?
C1 N29 C13 128.35(13) . . ?
C3 N29 C13 120.57(13) . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

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

data_HS121
_database_code_depnum_ccdc_archive 'CCDC 1529576'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C39 H46 B2 N2 O4), C7 H8'
_chemical_formula_sum            'C85 H100 B4 N4 O8'
_chemical_formula_weight         1348.92

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

_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                   12.395(2)
_cell_length_b                   14.186(2)
_cell_length_c                   23.450(4)
_cell_angle_alpha                90.354(4)
_cell_angle_beta                 96.904(4)
_cell_angle_gamma                98.937(4)
_cell_volume                     4042.6(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9350
_cell_measurement_theta_min      2.284
_cell_measurement_theta_max      26.0885

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_F_000             1444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/4 (Bruker 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45950
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.453
_diffrn_reflns_theta_max         26.097
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             16033
_reflns_number_gt                12724
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0508P)²+1.5916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16033
_refine_ls_number_parameters     928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.57218(11) 0.19601(9) 0.23894(5) 0.0149(3) Uani 1 1 d . . . . .
O1 O 0.49178(9) 0.09775(8) 0.36000(4) 0.0270(2) Uani 1 1 d . . . . .
B1 B 0.51932(13) 0.04728(11) 0.31389(7) 0.0187(3) Uani 1 1 d . . . . .
N1 N 0.63301(9) 0.28180(8) 0.24783(5) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.57001(11) 0.35907(10) 0.22909(6) 0.0198(3) Uani 1 1 d . . . . .
H2A H 0.6127 0.4065 0.2063 0.024 Uiso 1 1 calc R U . . .
H2B H 0.5486 0.3920 0.2623 0.024 Uiso 1 1 calc R U . . .
N2 N 0.47479(9) 0.20513(8) 0.20951(5) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.48722(8) -0.05060(7) 0.32021(4) 0.0239(2) Uani 1 1 d . . . . .
B2 B 0.60437(12) 0.09507(11) 0.26471(6) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.46991(12) 0.30465(10) 0.19248(6) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.4011 0.3255 0.2015 0.024 Uiso 1 1 calc R U . . .
H3B H 0.4757 0.3126 0.1510 0.024 Uiso 1 1 calc R U . . .
B3 B 0.36792(13) 0.52035(11) 0.28003(7) 0.0191(3) Uani 1 1 d . . . . .
N3 N 0.49195(9) 0.70997(8) 0.21426(5) 0.0156(2) Uani 1 1 d . . . . .
O3 O 0.61255(7) 0.02894(6) 0.21565(4) 0.0168(2) Uani 1 1 d . . . . .
C4 C 0.74634(11) 0.30768(9) 0.27296(6) 0.0169(3) Uani 1 1 d . . . . .
B4 B 0.34025(13) 0.55357(11) 0.20954(7) 0.0178(3) Uani 1 1 d . . . . .
N4 N 0.32566(9) 0.73604(8) 0.18537(5) 0.0163(2) Uani 1 1 d . . . . .
O4 O 0.71753(8) 0.11169(7) 0.29803(4) 0.0184(2) Uani 1 1 d . . . . .
C5 C 0.82919(11) 0.30455(10) 0.23733(6) 0.0187(3) Uani 1 1 d . . . . .
O5 O 0.36139(9) 0.57227(7) 0.32987(4) 0.0240(2) Uani 1 1 d . . . . .
C6 C 0.93635(12) 0.34267(10) 0.26006(6) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.9945 0.3427 0.2371 0.028 Uiso 1 1 calc R U . . .
O6 O 0.37957(9) 0.42660(7) 0.29417(4) 0.0225(2) Uani 1 1 d . . . . .
C7 C 0.95943(12) 0.38046(11) 0.31555(6) 0.0260(3) Uani 1 1 d . . . . .
H7 H 1.0328 0.4075 0.3299 0.031 Uiso 1 1 calc R U . . .
O7 O 0.21742(8) 0.53734(7) 0.19660(4) 0.0215(2) Uani 1 1 d . . . . .
C8 C 0.87678(12) 0.37927(10) 0.35034(6) 0.0240(3) Uani 1 1 d . . . . .
H8 H 0.8941 0.4037 0.3887 0.029 Uiso 1 1 calc R U . . .
O8 O 0.37810(8) 0.49089(7) 0.16665(4) 0.0192(2) Uani 1 1 d . . . . .
C9 C 0.76813(12) 0.34248(10) 0.32955(6) 0.0198(3) Uani 1 1 d . . . . .
C10 C 0.80317(12) 0.26141(10) 0.17662(6) 0.0214(3) Uani 1 1 d . . . . .
H10 H 0.7367 0.2114 0.1762 0.026 Uiso 1 1 calc R U . . .
C11 C 0.89579(13) 0.21253(11) 0.15813(7) 0.0262(3) Uani 1 1 d . . . . .
H11A H 0.8703 0.1780 0.1215 0.039 Uiso 1 1 calc R U . . .
H11B H 0.9165 0.1675 0.1875 0.039 Uiso 1 1 calc R U . . .
H11C H 0.9597 0.2608 0.1537 0.039 Uiso 1 1 calc R U . . .
C85 C -0.0229(2) 0.07594(16) 0.57963(8) 0.0553(6) Uani 1 1 d . . . . .
H85A H -0.1031 0.0692 0.5784 0.083 Uiso 1 1 calc R U . . .
H85B H 0.0122 0.1175 0.6124 0.083 Uiso 1 1 calc R U . . .
H85C H 0.0000 0.0130 0.5838 0.083 Uiso 1 1 calc R U . . .
C84 C 0.12071(16) 0.13380(15) 0.51454(9) 0.0489(5) Uani 1 1 d . . . . .
H84 H 0.1756 0.1153 0.5422 0.059 Uiso 1 1 calc R U . . .
C83 C 0.15017(18) 0.17515(16) 0.46439(10) 0.0570(6) Uani 1 1 d . . . . .
H83 H 0.2254 0.1853 0.4581 0.068 Uiso 1 1 calc R U . . .
C82 C 0.07307(18) 0.20171(15) 0.42366(10) 0.0524(5) Uani 1 1 d . . . . .
H82 H 0.0945 0.2304 0.3894 0.063 Uiso 1 1 calc R U . . .
C81 C -0.03512(17) 0.18669(14) 0.43253(8) 0.0435(4) Uani 1 1 d . . . . .
H81 H -0.0893 0.2044 0.4042 0.052 Uiso 1 1 calc R U . . .
C80 C -0.06582(15) 0.14570(13) 0.48270(8) 0.0381(4) Uani 1 1 d . . . . .
H80 H -0.1413 0.1356 0.4883 0.046 Uiso 1 1 calc R U . . .
C79 C 0.01089(15) 0.11905(13) 0.52494(7) 0.0371(4) Uani 1 1 d . . . . .
C78 C 0.28651(12) 0.45587(10) 0.12957(6) 0.0226(3) Uani 1 1 d . . . . .
C77 C 0.28065(14) 0.40145(11) 0.08016(7) 0.0303(3) Uani 1 1 d . . . . .
H77 H 0.3443 0.3811 0.0685 0.036 Uiso 1 1 calc R U . . .
C76 C 0.17703(16) 0.37716(13) 0.04762(8) 0.0416(4) Uani 1 1 d . . . . .
H76 H 0.1705 0.3397 0.0133 0.050 Uiso 1 1 calc R U . . .
C75 C 0.08475(15) 0.40664(13) 0.06461(8) 0.0446(5) Uani 1 1 d . . . . .
H75 H 0.0158 0.3896 0.0416 0.054 Uiso 1 1 calc R U . . .
C74 C 0.09086(13) 0.46110(12) 0.11507(7) 0.0338(4) Uani 1 1 d . . . . .
H74 H 0.0273 0.4813 0.1269 0.041 Uiso 1 1 calc R U . . .
C73 C 0.19251(12) 0.48438(10) 0.14703(6) 0.0231(3) Uani 1 1 d . . . . .
C72 C 0.37751(12) 0.42089(10) 0.35288(6) 0.0212(3) Uani 1 1 d . . . . .
C71 C 0.38706(14) 0.34371(11) 0.38748(6) 0.0296(3) Uani 1 1 d . . . . .
H71 H 0.3951 0.2833 0.3723 0.036 Uiso 1 1 calc R U . . .
C70 C 0.38431(14) 0.35913(12) 0.44590(7) 0.0326(4) Uani 1 1 d . . . . .
H70 H 0.3908 0.3080 0.4714 0.039 Uiso 1 1 calc R U . . .
C69 C 0.37235(15) 0.44703(13) 0.46767(7) 0.0356(4) Uani 1 1 d . . . . .
H69 H 0.3701 0.4548 0.5078 0.043 Uiso 1 1 calc R U . . .
C68 C 0.36351(14) 0.52467(13) 0.43222(7) 0.0333(4) Uani 1 1 d . . . . .
H68 H 0.3560 0.5854 0.4471 0.040 Uiso 1 1 calc R U . . .
C67 C 0.36626(12) 0.50878(11) 0.37451(6) 0.0228(3) Uani 1 1 d . . . . .
C66 C 0.28027(14) 0.65058(12) 0.04189(7) 0.0299(3) Uani 1 1 d . . . . .
H66A H 0.2120 0.6126 0.0235 0.045 Uiso 1 1 calc R U . . .
H66B H 0.3109 0.6160 0.0744 0.045 Uiso 1 1 calc R U . . .
H66C H 0.3335 0.6619 0.0140 0.045 Uiso 1 1 calc R U . . .
C65 C 0.21673(13) 0.80434(11) 0.01236(6) 0.0247(3) Uani 1 1 d . . . . .
H65A H 0.2771 0.8224 -0.0108 0.037 Uiso 1 1 calc R U . . .
H65B H 0.1933 0.8621 0.0267 0.037 Uiso 1 1 calc R U . . .
H65C H 0.1547 0.7660 -0.0113 0.037 Uiso 1 1 calc R U . . .
C64 C 0.25595(12) 0.74594(11) 0.06330(6) 0.0224(3) Uani 1 1 d . . . . .
H64 H 0.3266 0.7823 0.0826 0.027 Uiso 1 1 calc R U . . .
C63 C 0.15333(16) 0.81558(15) 0.29919(8) 0.0454(5) Uani 1 1 d . . . . .
H63A H 0.1941 0.8696 0.2810 0.068 Uiso 1 1 calc R U . . .
H63B H 0.1795 0.8170 0.3404 0.068 Uiso 1 1 calc R U . . .
H63C H 0.0747 0.8201 0.2938 0.068 Uiso 1 1 calc R U . . .
C62 C 0.11264(15) 0.63598(15) 0.30067(7) 0.0423(5) Uani 1 1 d . . . . .
H62A H 0.0347 0.6416 0.2998 0.063 Uiso 1 1 calc R U . . .
H62B H 0.1459 0.6340 0.3406 0.063 Uiso 1 1 calc R U . . .
H62C H 0.1195 0.5772 0.2801 0.063 Uiso 1 1 calc R U . . .
C61 C 0.17165(13) 0.72190(12) 0.27174(6) 0.0279(3) Uani 1 1 d . . . . .
H61 H 0.2523 0.7191 0.2776 0.033 Uiso 1 1 calc R U . . .
C60 C 0.17475(11) 0.73256(10) 0.10767(6) 0.0209(3) Uani 1 1 d . . . . .
C59 C 0.06245(12) 0.72657(12) 0.09017(7) 0.0280(3) Uani 1 1 d . . . . .
H59 H 0.0368 0.7287 0.0504 0.034 Uiso 1 1 calc R U . . .
C58 C -0.01230(12) 0.71748(12) 0.12997(7) 0.0310(4) Uani 1 1 d . . . . .
H58 H -0.0888 0.7123 0.1174 0.037 Uiso 1 1 calc R U . . .
C57 C 0.02399(12) 0.71589(11) 0.18784(7) 0.0273(3) Uani 1 1 d . . . . .
H57 H -0.0280 0.7111 0.2147 0.033 Uiso 1 1 calc R U . . .
C56 C 0.13528(12) 0.72114(10) 0.20764(6) 0.0216(3) Uani 1 1 d . . . . .
C55 C 0.20886(11) 0.72683(9) 0.16657(6) 0.0175(3) Uani 1 1 d . . . . .
C54 C 0.61580(13) 0.68306(11) 0.38624(6) 0.0278(3) Uani 1 1 d . . . . .
H54A H 0.5668 0.6216 0.3810 0.042 Uiso 1 1 calc R U . . .
H54B H 0.5890 0.7232 0.4139 0.042 Uiso 1 1 calc R U . . .
H54C H 0.6903 0.6724 0.4008 0.042 Uiso 1 1 calc R U . . .
C53 C 0.70066(13) 0.82588(11) 0.33608(7) 0.0298(3) Uani 1 1 d . . . . .
H53A H 0.7040 0.8569 0.2990 0.045 Uiso 1 1 calc R U . . .
H53B H 0.7735 0.8113 0.3506 0.045 Uiso 1 1 calc R U . . .
H53C H 0.6774 0.8688 0.3635 0.045 Uiso 1 1 calc R U . . .
C52 C 0.61769(12) 0.73305(10) 0.32850(6) 0.0216(3) Uani 1 1 d . . . . .
H52 H 0.5430 0.7499 0.3166 0.026 Uiso 1 1 calc R U . . .
C51 C 0.63868(14) 0.70361(12) 0.08472(7) 0.0307(4) Uani 1 1 d . . . . .
H51A H 0.7137 0.6907 0.0832 0.046 Uiso 1 1 calc R U . . .
H51B H 0.6414 0.7649 0.1048 0.046 Uiso 1 1 calc R U . . .
H51C H 0.6017 0.7062 0.0455 0.046 Uiso 1 1 calc R U . . .
C50 C 0.56734(14) 0.52886(12) 0.08426(7) 0.0295(3) Uani 1 1 d . . . . .
H50A H 0.5207 0.5301 0.0475 0.044 Uiso 1 1 calc R U . . .
H50B H 0.5354 0.4766 0.1072 0.044 Uiso 1 1 calc R U . . .
H50C H 0.6412 0.5191 0.0771 0.044 Uiso 1 1 calc R U . . .
C49 C 0.57481(12) 0.62373(10) 0.11694(6) 0.0207(3) Uani 1 1 d . . . . .
H49 H 0.4984 0.6379 0.1174 0.025 Uiso 1 1 calc R U . . .
C48 C 0.64672(11) 0.67211(10) 0.28065(6) 0.0183(3) Uani 1 1 d . . . . .
C47 C 0.74149(11) 0.62931(10) 0.28994(6) 0.0220(3) Uani 1 1 d . . . . .
H47 H 0.7813 0.6322 0.3273 0.026 Uiso 1 1 calc R U . . .
C46 C 0.77815(11) 0.58300(10) 0.24598(6) 0.0232(3) Uani 1 1 d . . . . .
H46 H 0.8410 0.5522 0.2535 0.028 Uiso 1 1 calc R U . . .
C45 C 0.72337(11) 0.58131(10) 0.19094(6) 0.0207(3) Uani 1 1 d . . . . .
H45 H 0.7517 0.5521 0.1606 0.025 Uiso 1 1 calc R U . . .
C44 C 0.62752(11) 0.62147(10) 0.17886(6) 0.0180(3) Uani 1 1 d . . . . .
C43 C 0.58826(11) 0.66394(9) 0.22506(6) 0.0164(3) Uani 1 1 d . . . . .
C42 C 0.38893(11) 0.83293(10) 0.19738(6) 0.0213(3) Uani 1 1 d . . . . .
H42A H 0.3722 0.8608 0.2335 0.026 Uiso 1 1 calc R U . . .
H42B H 0.3741 0.8762 0.1654 0.026 Uiso 1 1 calc R U . . .
C41 C 0.50645(11) 0.81335(10) 0.20279(6) 0.0201(3) Uani 1 1 d . . . . .
H41A H 0.5395 0.8274 0.1668 0.024 Uiso 1 1 calc R U . . .
H41B H 0.5528 0.8510 0.2350 0.024 Uiso 1 1 calc R U . . .
C40 C 0.38707(11) 0.66860(9) 0.20045(5) 0.0151(3) Uani 1 1 d . . . . .
C12 C 0.77414(14) 0.33583(12) 0.13283(7) 0.0316(4) Uani 1 1 d . . . . .
H12A H 0.7564 0.3056 0.0945 0.047 Uiso 1 1 calc R U . . .
H12B H 0.8370 0.3871 0.1329 0.047 Uiso 1 1 calc R U . . .
H12C H 0.7104 0.3624 0.1431 0.047 Uiso 1 1 calc R U . . .
C13 C 0.67863(12) 0.33926(10) 0.36891(6) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.6073 0.3108 0.3463 0.027 Uiso 1 1 calc R U . . .
C14 C 0.69916(14) 0.27578(13) 0.42027(7) 0.0337(4) Uani 1 1 d . . . . .
H14A H 0.7074 0.2122 0.4065 0.051 Uiso 1 1 calc R U . . .
H14B H 0.6368 0.2704 0.4427 0.051 Uiso 1 1 calc R U . . .
H14C H 0.7665 0.3040 0.4445 0.051 Uiso 1 1 calc R U . . .
C15 C 0.66719(14) 0.43949(12) 0.38887(7) 0.0322(4) Uani 1 1 d . . . . .
H15A H 0.6510 0.4781 0.3553 0.048 Uiso 1 1 calc R U . . .
H15B H 0.7361 0.4691 0.4113 0.048 Uiso 1 1 calc R U . . .
H15C H 0.6071 0.4355 0.4128 0.048 Uiso 1 1 calc R U . . .
C16 C 0.38845(11) 0.13061(9) 0.18528(6) 0.0160(3) Uani 1 1 d . . . . .
C17 C 0.29154(11) 0.11312(10) 0.21143(6) 0.0193(3) Uani 1 1 d . . . . .
C18 C 0.20538(12) 0.04520(10) 0.18523(6) 0.0232(3) Uani 1 1 d . . . . .
H18 H 0.1397 0.0307 0.2027 0.028 Uiso 1 1 calc R U . . .
C19 C 0.21420(12) -0.00088(10) 0.13449(6) 0.0232(3) Uani 1 1 d . . . . .
H19 H 0.1553 -0.0473 0.1176 0.028 Uiso 1 1 calc R U . . .
C20 C 0.30886(12) 0.02049(10) 0.10821(6) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.3132 -0.0104 0.0727 0.025 Uiso 1 1 calc R U . . .
C21 C 0.39796(11) 0.08637(10) 0.13270(6) 0.0176(3) Uani 1 1 d . . . . .
C22 C 0.27523(12) 0.16820(11) 0.26455(6) 0.0239(3) Uani 1 1 d . . . . .
H22 H 0.3478 0.2057 0.2805 0.029 Uiso 1 1 calc R U . . .
C23 C 0.23354(13) 0.10173(13) 0.31131(7) 0.0322(4) Uani 1 1 d . . . . .
H23A H 0.1557 0.0759 0.3003 0.048 Uiso 1 1 calc R U . . .
H23B H 0.2419 0.1377 0.3478 0.048 Uiso 1 1 calc R U . . .
H23C H 0.2764 0.0491 0.3157 0.048 Uiso 1 1 calc R U . . .
C24 C 0.19455(13) 0.23853(12) 0.24857(8) 0.0339(4) Uani 1 1 d . . . . .
H24A H 0.2218 0.2810 0.2189 0.051 Uiso 1 1 calc R U . . .
H24B H 0.1882 0.2765 0.2827 0.051 Uiso 1 1 calc R U . . .
H24C H 0.1222 0.2029 0.2339 0.051 Uiso 1 1 calc R U . . .
C25 C 0.49700(12) 0.11105(10) 0.10016(6) 0.0202(3) Uani 1 1 d . . . . .
H25 H 0.5571 0.1504 0.1263 0.024 Uiso 1 1 calc R U . . .
C26 C 0.53988(13) 0.02185(11) 0.08088(6) 0.0250(3) Uani 1 1 d . . . . .
H26A H 0.4846 -0.0147 0.0524 0.038 Uiso 1 1 calc R U . . .
H26B H 0.5545 -0.0178 0.1142 0.038 Uiso 1 1 calc R U . . .
H26C H 0.6080 0.0410 0.0638 0.038 Uiso 1 1 calc R U . . .
C27 C 0.46714(13) 0.17113(11) 0.04793(6) 0.0269(3) Uani 1 1 d . . . . .
H27A H 0.5323 0.1896 0.0282 0.040 Uiso 1 1 calc R U . . .
H27B H 0.4413 0.2286 0.0608 0.040 Uiso 1 1 calc R U . . .
H27C H 0.4088 0.1335 0.0215 0.040 Uiso 1 1 calc R U . . .
C28 C 0.44419(13) 0.02979(13) 0.39528(6) 0.0303(4) Uani 1 1 d . . . . .
C29 C 0.40217(15) 0.04342(16) 0.44598(7) 0.0451(5) Uani 1 1 d . . . . .
H29 H 0.4041 0.1053 0.4622 0.054 Uiso 1 1 calc R U . . .
C30 C 0.35690(16) -0.0387(2) 0.47191(8) 0.0551(6) Uani 1 1 d . . . . .
H30 H 0.3265 -0.0329 0.5069 0.066 Uiso 1 1 calc R U . . .
C31 C 0.35481(15) -0.12894(18) 0.44812(8) 0.0523(6) Uani 1 1 d . . . . .
H31 H 0.3231 -0.1833 0.4672 0.063 Uiso 1 1 calc R U . . .
C32 C 0.39808(14) -0.14162(14) 0.39694(8) 0.0406(4) Uani 1 1 d . . . . .
H32 H 0.3974 -0.2032 0.3806 0.049 Uiso 1 1 calc R U . . .
C33 C 0.44187(12) -0.05949(12) 0.37152(6) 0.0279(3) Uani 1 1 d . . . . .
C34 C 0.71827(11) 0.01037(9) 0.22262(6) 0.0177(3) Uani 1 1 d . . . . .
C35 C 0.76405(12) -0.04843(10) 0.18863(6) 0.0230(3) Uani 1 1 d . . . . .
H35 H 0.7237 -0.0784 0.1546 0.028 Uiso 1 1 calc R U . . .
C36 C 0.87270(12) -0.06227(11) 0.20631(7) 0.0288(3) Uani 1 1 d . . . . .
H36 H 0.9064 -0.1030 0.1841 0.035 Uiso 1 1 calc R U . . .
C37 C 0.93106(12) -0.01749(11) 0.25534(7) 0.0286(3) Uani 1 1 d . . . . .
H37 H 1.0039 -0.0291 0.2668 0.034 Uiso 1 1 calc R U . . .
C38 C 0.88555(12) 0.04464(11) 0.28866(7) 0.0239(3) Uani 1 1 d . . . . .
H38 H 0.9267 0.0767 0.3219 0.029 Uiso 1 1 calc R U . . .
C39 C 0.77878(11) 0.05743(9) 0.27143(6) 0.0181(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3294(17) . ?
C1 N2 1.3415(17) . ?
C1 B2 1.645(2) . ?
O1 C28 1.3829(18) . ?
O1 B1 1.3977(19) . ?
B1 O2 1.3977(19) . ?
B1 B2 1.726(2) . ?
N1 C4 1.4469(17) . ?
N1 C2 1.4812(17) . ?
C2 C3 1.5201(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C16 1.4425(17) . ?
N2 C3 1.4779(17) . ?
O2 C33 1.3864(17) . ?
B2 O3 1.5027(17) . ?
B2 O4 1.5050(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
B3 O5 1.3949(19) . ?
B3 O6 1.3976(19) . ?
B3 B4 1.731(2) . ?
N3 C40 1.3412(17) . ?
N3 C43 1.4446(17) . ?
N3 C41 1.4799(17) . ?
O3 C34 1.3674(16) . ?
C4 C9 1.3935(19) . ?
C4 C5 1.4053(19) . ?
B4 O7 1.4974(18) . ?
B4 O8 1.5015(18) . ?
B4 C40 1.669(2) . ?
N4 C40 1.3362(17) . ?
N4 C55 1.4473(17) . ?
N4 C42 1.4802(17) . ?
O4 C39 1.3592(16) . ?
C5 C6 1.394(2) . ?
C5 C10 1.524(2) . ?
O5 C67 1.3871(17) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
O6 C72 1.3828(16) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
O7 C73 1.3571(17) . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
O8 C78 1.3689(17) . ?
C9 C13 1.5216(19) . ?
C10 C12 1.530(2) . ?
C10 C11 1.5330(19) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C85 C79 1.501(3) . ?
C85 H85A 0.9800 . ?
C85 H85B 0.9800 . ?
C85 H85C 0.9800 . ?
C84 C83 1.380(3) . ?
C84 C79 1.396(3) . ?
C84 H84 0.9500 . ?
C83 C82 1.366(3) . ?
C83 H83 0.9500 . ?
C82 C81 1.366(3) . ?
C82 H82 0.9500 . ?
C81 C80 1.384(2) . ?
C81 H81 0.9500 . ?
C80 C79 1.385(3) . ?
C80 H80 0.9500 . ?
C78 C77 1.377(2) . ?
C78 C73 1.396(2) . ?
C77 C76 1.405(2) . ?
C77 H77 0.9500 . ?
C76 C75 1.378(3) . ?
C76 H76 0.9500 . ?
C75 C74 1.397(3) . ?
C75 H75 0.9500 . ?
C74 C73 1.378(2) . ?
C74 H74 0.9500 . ?
C72 C67 1.376(2) . ?
C72 C71 1.378(2) . ?
C71 C70 1.391(2) . ?
C71 H71 0.9500 . ?
C70 C69 1.380(3) . ?
C70 H70 0.9500 . ?
C69 C68 1.394(2) . ?
C69 H69 0.9500 . ?
C68 C67 1.376(2) . ?
C68 H68 0.9500 . ?
C66 C64 1.526(2) . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C65 C64 1.532(2) . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C64 C60 1.5254(19) . ?
C64 H64 1.0000 . ?
C63 C61 1.533(2) . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C62 C61 1.528(2) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C61 C56 1.516(2) . ?
C61 H61 1.0000 . ?
C60 C59 1.392(2) . ?
C60 C55 1.4016(19) . ?
C59 C58 1.385(2) . ?
C59 H59 0.9500 . ?
C58 C57 1.379(2) . ?
C58 H58 0.9500 . ?
C57 C56 1.392(2) . ?
C57 H57 0.9500 . ?
C56 C55 1.3982(19) . ?
C54 C52 1.5331(19) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C53 C52 1.535(2) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C52 C48 1.5225(19) . ?
C52 H52 1.0000 . ?
C51 C49 1.535(2) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C50 C49 1.529(2) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C49 C44 1.5217(19) . ?
C49 H49 1.0000 . ?
C48 C47 1.399(2) . ?
C48 C43 1.4081(19) . ?
C47 C46 1.378(2) . ?
C47 H47 0.9500 . ?
C46 C45 1.383(2) . ?
C46 H46 0.9500 . ?
C45 C44 1.3956(19) . ?
C45 H45 0.9500 . ?
C44 C43 1.4083(19) . ?
C42 C41 1.5156(19) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.527(2) . ?
C13 C14 1.529(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.4025(19) . ?
C16 C21 1.4058(19) . ?
C17 C18 1.401(2) . ?
C17 C22 1.5169(19) . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20 0.9500 . ?
C21 C25 1.5188(19) . ?
C22 C23 1.535(2) . ?
C22 C24 1.536(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.532(2) . ?
C25 C27 1.538(2) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.375(2) . ?
C28 C29 1.378(2) . ?
C29 C30 1.389(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.394(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.377(2) . ?
C32 H32 0.9500 . ?
C34 C35 1.3786(19) . ?
C34 C39 1.395(2) . ?
C35 C36 1.405(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.399(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.376(2) . ?
C38 H38 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 109.17(11) . . ?
N1 C1 B2 126.20(12) . . ?
N2 C1 B2 124.39(11) . . ?
C28 O1 B1 106.02(12) . . ?
O2 B1 O1 109.78(12) . . ?
O2 B1 B2 123.93(12) . . ?
O1 B1 B2 125.07(12) . . ?
C1 N1 C4 129.63(11) . . ?
C1 N1 C2 111.89(11) . . ?
C4 N1 C2 118.47(11) . . ?
N1 C2 C3 102.18(11) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C1 N2 C16 128.15(11) . . ?
C1 N2 C3 111.94(11) . . ?
C16 N2 C3 118.86(10) . . ?
C33 O2 B1 105.76(12) . . ?
O3 B2 O4 105.04(10) . . ?
O3 B2 C1 109.14(10) . . ?
O4 B2 C1 110.28(11) . . ?
O3 B2 B1 115.05(11) . . ?
O4 B2 B1 104.37(10) . . ?
C1 B2 B1 112.54(11) . . ?
N2 C3 C2 102.01(11) . . ?
N2 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
N2 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.2 . . ?
O5 B3 O6 109.35(12) . . ?
O5 B3 B4 127.68(13) . . ?
O6 B3 B4 121.89(12) . . ?
C40 N3 C43 127.82(11) . . ?
C40 N3 C41 111.50(11) . . ?
C43 N3 C41 118.96(10) . . ?
C34 O3 B2 105.97(10) . . ?
C9 C4 C5 122.92(12) . . ?
C9 C4 N1 118.81(12) . . ?
C5 C4 N1 118.02(12) . . ?
O7 B4 O8 104.64(11) . . ?
O7 B4 C40 108.74(11) . . ?
O8 B4 C40 111.34(11) . . ?
O7 B4 B3 105.62(11) . . ?
O8 B4 B3 113.74(11) . . ?
C40 B4 B3 112.18(11) . . ?
C40 N4 C55 129.61(11) . . ?
C40 N4 C42 111.50(11) . . ?
C55 N4 C42 118.42(11) . . ?
C39 O4 B2 106.30(10) . . ?
C6 C5 C4 116.95(13) . . ?
C6 C5 C10 121.49(12) . . ?
C4 C5 C10 121.56(12) . . ?
C67 O5 B3 106.22(11) . . ?
C7 C6 C5 121.09(13) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C72 O6 B3 106.40(11) . . ?
C8 C7 C6 120.62(13) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C73 O7 B4 106.58(11) . . ?
C7 C8 C9 120.53(14) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C78 O8 B4 106.00(11) . . ?
C4 C9 C8 117.81(13) . . ?
C4 C9 C13 122.33(12) . . ?
C8 C9 C13 119.84(13) . . ?
C5 C10 C12 111.50(12) . . ?
C5 C10 C11 113.13(12) . . ?
C12 C10 C11 110.09(12) . . ?
C5 C10 H10 107.3 . . ?
C12 C10 H10 107.3 . . ?
C11 C10 H10 107.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C79 C85 H85A 109.5 . . ?
C79 C85 H85B 109.5 . . ?
H85A C85 H85B 109.5 . . ?
C79 C85 H85C 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?
C83 C84 C79 120.44(19) . . ?
C83 C84 H84 119.8 . . ?
C79 C84 H84 119.8 . . ?
C82 C83 C84 121.12(19) . . ?
C82 C83 H83 119.4 . . ?
C84 C83 H83 119.4 . . ?
C83 C82 C81 119.46(19) . . ?
C83 C82 H82 120.3 . . ?
C81 C82 H82 120.3 . . ?
C82 C81 C80 120.06(19) . . ?
C82 C81 H81 120.0 . . ?
C80 C81 H81 120.0 . . ?
C81 C80 C79 121.60(17) . . ?
C81 C80 H80 119.2 . . ?
C79 C80 H80 119.2 . . ?
C80 C79 C84 117.30(17) . . ?
C80 C79 C85 121.26(18) . . ?
C84 C79 C85 121.44(18) . . ?
O8 C78 C77 127.92(14) . . ?
O8 C78 C73 111.01(12) . . ?
C77 C78 C73 121.05(14) . . ?
C78 C77 C76 117.52(16) . . ?
C78 C77 H77 121.2 . . ?
C76 C77 H77 121.2 . . ?
C75 C76 C77 121.19(16) . . ?
C75 C76 H76 119.4 . . ?
C77 C76 H76 119.4 . . ?
C76 C75 C74 121.11(16) . . ?
C76 C75 H75 119.4 . . ?
C74 C75 H75 119.4 . . ?
C73 C74 C75 117.54(16) . . ?
C73 C74 H74 121.2 . . ?
C75 C74 H74 121.2 . . ?
O7 C73 C74 127.40(14) . . ?
O7 C73 C78 111.02(12) . . ?
C74 C73 C78 121.56(14) . . ?
C67 C72 C71 122.28(13) . . ?
C67 C72 O6 108.96(12) . . ?
C71 C72 O6 128.74(13) . . ?
C72 C71 C70 116.33(15) . . ?
C72 C71 H71 121.8 . . ?
C70 C71 H71 121.8 . . ?
C69 C70 C71 121.52(15) . . ?
C69 C70 H70 119.2 . . ?
C71 C70 H70 119.2 . . ?
C70 C69 C68 121.56(14) . . ?
C70 C69 H69 119.2 . . ?
C68 C69 H69 119.2 . . ?
C67 C68 C69 116.53(15) . . ?
C67 C68 H68 121.7 . . ?
C69 C68 H68 121.7 . . ?
C68 C67 C72 121.78(14) . . ?
C68 C67 O5 129.16(14) . . ?
C72 C67 O5 109.04(12) . . ?
C64 C66 H66A 109.5 . . ?
C64 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C64 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C64 C65 H65A 109.5 . . ?
C64 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
C64 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C60 C64 C66 111.73(12) . . ?
C60 C64 C65 112.28(12) . . ?
C66 C64 C65 110.07(12) . . ?
C60 C64 H64 107.5 . . ?
C66 C64 H64 107.5 . . ?
C65 C64 H64 107.5 . . ?
C61 C63 H63A 109.5 . . ?
C61 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C61 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C56 C61 C62 112.07(14) . . ?
C56 C61 C63 109.62(13) . . ?
C62 C61 C63 110.88(14) . . ?
C56 C61 H61 108.0 . . ?
C62 C61 H61 108.0 . . ?
C63 C61 H61 108.0 . . ?
C59 C60 C55 117.73(13) . . ?
C59 C60 C64 119.94(13) . . ?
C55 C60 C64 122.32(12) . . ?
C58 C59 C60 120.81(14) . . ?
C58 C59 H59 119.6 . . ?
C60 C59 H59 119.6 . . ?
C57 C58 C59 120.19(14) . . ?
C57 C58 H58 119.9 . . ?
C59 C58 H58 119.9 . . ?
C58 C57 C56 121.32(14) . . ?
C58 C57 H57 119.3 . . ?
C56 C57 H57 119.3 . . ?
C57 C56 C55 117.49(13) . . ?
C57 C56 C61 119.46(13) . . ?
C55 C56 C61 123.05(13) . . ?
C56 C55 C60 122.34(12) . . ?
C56 C55 N4 119.28(12) . . ?
C60 C55 N4 118.13(12) . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C48 C52 C54 113.68(12) . . ?
C48 C52 C53 109.04(12) . . ?
C54 C52 C53 109.27(12) . . ?
C48 C52 H52 108.2 . . ?
C54 C52 H52 108.2 . . ?
C53 C52 H52 108.2 . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C44 C49 C50 112.90(12) . . ?
C44 C49 C51 110.45(12) . . ?
C50 C49 C51 109.25(12) . . ?
C44 C49 H49 108.0 . . ?
C50 C49 H49 108.0 . . ?
C51 C49 H49 108.0 . . ?
C47 C48 C43 117.64(13) . . ?
C47 C48 C52 119.24(12) . . ?
C43 C48 C52 122.83(12) . . ?
C46 C47 C48 121.30(13) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C47 C46 C45 119.96(13) . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C45 C44 121.61(13) . . ?
C46 C45 H45 119.2 . . ?
C44 C45 H45 119.2 . . ?
C45 C44 C43 117.40(13) . . ?
C45 C44 C49 119.47(12) . . ?
C43 C44 C49 122.99(12) . . ?
C48 C43 C44 121.85(12) . . ?
C48 C43 N3 118.40(12) . . ?
C44 C43 N3 119.39(12) . . ?
N4 C42 C41 101.76(11) . . ?
N4 C42 H42A 111.4 . . ?
C41 C42 H42A 111.4 . . ?
N4 C42 H42B 111.4 . . ?
C41 C42 H42B 111.4 . . ?
H42A C42 H42B 109.3 . . ?
N3 C41 C42 101.87(10) . . ?
N3 C41 H41A 111.4 . . ?
C42 C41 H41A 111.4 . . ?
N3 C41 H41B 111.4 . . ?
C42 C41 H41B 111.4 . . ?
H41A C41 H41B 109.3 . . ?
N4 C40 N3 108.96(11) . . ?
N4 C40 B4 126.03(12) . . ?
N3 C40 B4 124.53(11) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C15 111.15(12) . . ?
C9 C13 C14 111.56(12) . . ?
C15 C13 C14 110.84(13) . . ?
C9 C13 H13 107.7 . . ?
C15 C13 H13 107.7 . . ?
C14 C13 H13 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 121.86(12) . . ?
C17 C16 N2 118.36(12) . . ?
C21 C16 N2 119.29(12) . . ?
C18 C17 C16 117.83(13) . . ?
C18 C17 C22 119.55(12) . . ?
C16 C17 C22 122.54(12) . . ?
C19 C18 C17 121.13(13) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.00(13) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 121.44(13) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 117.64(12) . . ?
C20 C21 C25 118.99(12) . . ?
C16 C21 C25 123.27(12) . . ?
C17 C22 C23 112.01(13) . . ?
C17 C22 C24 110.13(12) . . ?
C23 C22 C24 109.88(13) . . ?
C17 C22 H22 108.2 . . ?
C23 C22 H22 108.2 . . ?
C24 C22 H22 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 C26 112.15(12) . . ?
C21 C25 C27 109.76(11) . . ?
C26 C25 C27 110.19(12) . . ?
C21 C25 H25 108.2 . . ?
C26 C25 H25 108.2 . . ?
C27 C25 H25 108.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 122.36(16) . . ?
C33 C28 O1 109.14(13) . . ?
C29 C28 O1 128.49(17) . . ?
C28 C29 C30 116.0(2) . . ?
C28 C29 H29 122.0 . . ?
C30 C29 H29 122.0 . . ?
C29 C30 C31 121.76(18) . . ?
C29 C30 H30 119.1 . . ?
C31 C30 H30 119.1 . . ?
C30 C31 C32 121.59(18) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C33 C32 C31 115.9(2) . . ?
C33 C32 H32 122.0 . . ?
C31 C32 H32 122.0 . . ?
C28 C33 C32 122.35(16) . . ?
C28 C33 O2 109.29(13) . . ?
C32 C33 O2 128.35(16) . . ?
O3 C34 C35 127.22(13) . . ?
O3 C34 C39 111.36(11) . . ?
C35 C34 C39 121.40(13) . . ?
C34 C35 C36 117.41(14) . . ?
C34 C35 H35 121.3 . . ?
C36 C35 H35 121.3 . . ?
C37 C36 C35 120.88(14) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 121.52(14) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C39 C38 C37 117.40(14) . . ?
C39 C38 H38 121.3 . . ?
C37 C38 H38 121.3 . . ?
O4 C39 C38 127.38(13) . . ?
O4 C39 C34 111.26(12) . . ?
C38 C39 C34 121.33(13) . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6



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

data_twin5l4
_database_code_depnum_ccdc_archive 'CCDC 1529577'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H44 B2 N4 O6, 2(C6 H6)'
_chemical_formula_sum            'C36 H56 B2 N4 O6'
_chemical_formula_weight         662.46

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

_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                   7.5233(13)
_cell_length_b                   12.070(2)
_cell_length_c                   21.443(4)
_cell_angle_alpha                94.556(5)
_cell_angle_beta                 92.752(5)
_cell_angle_gamma                106.214(5)
_cell_volume                     1858.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4770
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.12

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.447442
_exptl_absorpt_correction_T_max  0.745317
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7263
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_v_R_equivalents   ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.765
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7263
_reflns_number_gt                5598
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.4702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7263
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1878(4) 0.7421(3) -0.08011(15) 0.0139(7) Uani 1 1 d . . . . .
O1 O 0.5655(3) 0.8567(2) 0.03968(12) 0.0165(6) Uani 1 1 d . . . . .
C1 C 0.2805(5) 0.7355(3) -0.02542(18) 0.0148(8) Uani 1 1 d . . . . .
B1 B 0.5076(5) 0.7556(4) -0.0065(2) 0.0122(9) Uani 1 1 d . . . . .
N2 N 0.1528(4) 0.7202(3) 0.01777(15) 0.0148(7) Uani 1 1 d . . . . .
O2 O 0.6194(3) 0.7832(2) -0.06049(12) 0.0146(6) Uani 1 1 d . . . . .
B2 B 0.9649(5) 0.7409(4) 0.4945(2) 0.0121(9) Uani 1 1 d . . . . .
C2 C 0.0025(5) 0.7307(3) -0.07108(19) 0.0190(9) Uani 1 1 d . . . . .
H00P H -0.0913 0.7314 -0.1022 0.023 Uiso 1 1 calc R U . . .
N4 N 1.2584(4) 0.7278(3) 0.42410(15) 0.0139(7) Uani 1 1 d . . . . .
O4 O 0.9244(3) 0.6556(2) 0.54034(12) 0.0143(6) Uani 1 1 d . . . . .
C4 C 0.2667(5) 0.7549(3) -0.14227(18) 0.0157(8) Uani 1 1 d . . . . .
H00Q H 0.4033 0.7655 -0.1362 0.019 Uiso 1 1 calc R U . . .
C3 C -0.0192(5) 0.7184(3) -0.0098(2) 0.0181(9) Uani 1 1 d . . . . .
H00L H -0.1307 0.7101 0.0106 0.022 Uiso 1 1 calc R U . . .
O3 O 0.5324(3) 0.6532(2) 0.02036(12) 0.0142(6) Uani 1 1 d . . . . .
N3 N 1.3297(4) 0.7875(3) 0.52182(15) 0.0145(7) Uani 1 1 d . . . . .
C5 C 0.2378(6) 0.8621(4) -0.1692(2) 0.0246(9) Uani 1 1 d . . . . .
H00U H 0.3035 0.8751 -0.2075 0.037 Uiso 1 1 calc R U . . .
H00V H 0.2862 0.9296 -0.1383 0.037 Uiso 1 1 calc R U . . .
H00W H 0.1049 0.8505 -0.1791 0.037 Uiso 1 1 calc R U . . .
O5 O 0.8333(3) 0.6936(2) 0.43997(12) 0.0138(6) Uani 1 1 d . . . . .
C6 C 0.1815(6) 0.6450(4) -0.1857(2) 0.0257(10) Uani 1 1 d . . . . .
H01C H 0.0480 0.6342 -0.1933 0.039 Uiso 1 1 calc R U . . .
H01D H 0.2016 0.5784 -0.1662 0.039 Uiso 1 1 calc R U . . .
H01E H 0.2399 0.6517 -0.2257 0.039 Uiso 1 1 calc R U . . .
O6 O 0.9519(3) 0.8531(2) 0.52089(12) 0.0128(5) Uani 1 1 d . . . . .
C7 C 0.1900(5) 0.7111(3) 0.08466(19) 0.0199(9) Uani 1 1 d . . . . .
H00T H 0.3250 0.7176 0.0921 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0810(7) 0.5939(4) 0.1019(2) 0.0381(12) Uani 1 1 d . . . . .
H01O H -0.0521 0.5857 0.0955 0.057 Uiso 1 1 calc R U . . .
H01P H 0.1123 0.5868 0.1460 0.057 Uiso 1 1 calc R U . . .
H01Q H 0.1119 0.5330 0.0753 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1504(9) 0.8089(4) 0.1243(2) 0.0460(14) Uani 1 1 d . . . . .
H01R H 0.2165 0.8829 0.1094 0.069 Uiso 1 1 calc R U . . .
H01S H 0.1922 0.8073 0.1681 0.069 Uiso 1 1 calc R U . . .
H01T H 0.0167 0.8000 0.1211 0.069 Uiso 1 1 calc R U . . .
C20 C 1.2303(6) 0.7831(4) 0.3173(2) 0.0267(10) Uani 1 1 d . . . . .
H017 H 1.3588 0.7857 0.3097 0.040 Uiso 1 1 calc R U . . .
H018 H 1.2264 0.8591 0.3358 0.040 Uiso 1 1 calc R U . . .
H019 H 1.1539 0.7630 0.2775 0.040 Uiso 1 1 calc R U . . .
C21 C 1.1672(6) 0.5733(4) 0.3364(2) 0.0286(10) Uani 1 1 d . . . . .
H00X H 1.0946 0.5498 0.2960 0.043 Uiso 1 1 calc R U . . .
H00Y H 1.1171 0.5169 0.3662 0.043 Uiso 1 1 calc R U . . .
H00Z H 1.2970 0.5763 0.3309 0.043 Uiso 1 1 calc R U . . .
C22 C 0.7574(5) 0.5736(3) 0.44608(19) 0.0204(9) Uani 1 1 d . . . . .
H22 H 0.8329 0.5277 0.4258 0.024 Uiso 1 1 calc R U . . .
H00K H 0.6284 0.5452 0.4271 0.024 Uiso 1 1 calc R U . . .
C23 C 0.7633(5) 0.5660(3) 0.5166(2) 0.0235(9) Uani 1 1 d . . . . .
H00F H 0.6507 0.5791 0.5341 0.028 Uiso 1 1 calc R U . . .
H23 H 0.7735 0.4894 0.5267 0.028 Uiso 1 1 calc R U . . .
C24 C 0.9907(5) 0.9432(3) 0.48109(19) 0.0176(8) Uani 1 1 d . . . . .
H00C H 0.8892 0.9287 0.4477 0.021 Uiso 1 1 calc R U . . .
H00D H 1.1074 0.9460 0.4610 0.021 Uiso 1 1 calc R U . . .
C25 C 0.6572(6) 0.7938(4) 0.1874(2) 0.0329(11) Uani 1 1 d . . . . .
H01L H 0.6438 0.8389 0.1541 0.039 Uiso 1 1 calc R U . . .
C26 C 0.7303(6) 0.8478(4) 0.2458(2) 0.0312(11) Uani 1 1 d . . . . .
H01K H 0.7680 0.9300 0.2526 0.037 Uiso 1 1 calc R U . . .
C27 C 0.7486(5) 0.7828(4) 0.2942(2) 0.0284(10) Uani 1 1 d . . . . .
H01M H 0.8005 0.8203 0.3342 0.034 Uiso 1 1 calc R U . . .
C28 C 0.6925(6) 0.6641(4) 0.2850(2) 0.0303(11) Uani 1 1 d . . . . .
H010 H 0.7041 0.6197 0.3188 0.036 Uiso 1 1 calc R U . . .
C29 C 0.6185(6) 0.6087(4) 0.2261(2) 0.0318(11) Uani 1 1 d . . . . .
H01F H 0.5787 0.5265 0.2196 0.038 Uiso 1 1 calc R U . . .
C30 C 0.6034(6) 0.6743(4) 0.1772(2) 0.0337(11) Uani 1 1 d . . . . .
H01B H 0.5560 0.6372 0.1367 0.040 Uiso 1 1 calc R U . . .
C32 C 0.8194(6) 0.9276(4) 0.7342(2) 0.0300(10) Uani 1 1 d . . . . .
H01N H 0.8433 1.0094 0.7355 0.036 Uiso 1 1 calc R U . . .
C33 C 0.7286(5) 0.8692(4) 0.7814(2) 0.0264(10) Uani 1 1 d . . . . .
H011 H 0.6900 0.9106 0.8152 0.032 Uiso 1 1 calc R U . . .
C34 C 0.6940(5) 0.7509(4) 0.7797(2) 0.0231(9) Uani 1 1 d . . . . .
H012 H 0.6321 0.7103 0.8122 0.028 Uiso 1 1 calc R U . . .
C35 C 0.7500(5) 0.6918(4) 0.7303(2) 0.0268(10) Uani 1 1 d . . . . .
H01A H 0.7252 0.6100 0.7288 0.032 Uiso 1 1 calc R U . . .
C36 C 0.8410(6) 0.7493(4) 0.6832(2) 0.0314(11) Uani 1 1 d . . . . .
H013 H 0.8796 0.7075 0.6496 0.038 Uiso 1 1 calc R U . . .
C37 C 0.8761(6) 0.8674(4) 0.6847(2) 0.0327(11) Uani 1 1 d . . . . .
H01G H 0.9387 0.9077 0.6522 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7024(5) 0.9053(3) -0.05237(19) 0.0187(9) Uani 1 1 d . . . . .
H00N H 0.6227 0.9462 -0.0733 0.022 Uiso 1 1 calc R U . . .
H00O H 0.8254 0.9260 -0.0699 0.022 Uiso 1 1 calc R U . . .
C11 C 0.7214(5) 0.9365(3) 0.01788(19) 0.0204(9) Uani 1 1 d . . . . .
H00R H 0.8387 0.9274 0.0366 0.025 Uiso 1 1 calc R U . . .
H00S H 0.7182 1.0173 0.0281 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4861(5) 0.5478(3) -0.01875(18) 0.0160(8) Uani 1 1 d . . . . .
H00A H 0.5657 0.5559 -0.0545 0.019 Uiso 1 1 calc R U . . .
H00B H 0.3551 0.5284 -0.0356 0.019 Uiso 1 1 calc R U . . .
C13 C 1.1859(5) 0.7550(3) 0.47760(17) 0.0114(8) Uani 1 1 d . . . . .
C16 C 1.3165(5) 0.8250(3) 0.58838(17) 0.0164(8) Uani 1 1 d . . . . .
H16 H 1.1879 0.8310 0.5934 0.020 Uiso 1 1 calc R U . . .
C15 C 1.4471(5) 0.7435(3) 0.43518(19) 0.0171(8) Uani 1 1 d . . . . .
H15 H 1.5300 0.7313 0.4051 0.021 Uiso 1 1 calc R U . . .
C14 C 1.4914(5) 0.7793(3) 0.49612(19) 0.0168(8) Uani 1 1 d . . . . .
H00M H 1.6107 0.7958 0.5176 0.020 Uiso 1 1 calc R U . . .
C19 C 1.1562(5) 0.6927(3) 0.36177(18) 0.0162(8) Uani 1 1 d . . . . .
H19 H 1.0228 0.6878 0.3667 0.019 Uiso 1 1 calc R U . . .
C18 C 1.3498(7) 0.7366(4) 0.6305(2) 0.0299(10) Uani 1 1 d . . . . .
H01H H 1.2547 0.6624 0.6197 0.045 Uiso 1 1 calc R U . . .
H01I H 1.3435 0.7639 0.6744 0.045 Uiso 1 1 calc R U . . .
H01J H 1.4727 0.7262 0.6246 0.045 Uiso 1 1 calc R U . . .
C17 C 1.4519(6) 0.9451(4) 0.6050(2) 0.0284(10) Uani 1 1 d . . . . .
H014 H 1.5794 0.9401 0.6036 0.043 Uiso 1 1 calc R U . . .
H015 H 1.4331 0.9748 0.6473 0.043 Uiso 1 1 calc R U . . .
H016 H 1.4301 0.9976 0.5748 0.043 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
N1 C1 1.355(5) . ?
N1 C2 1.386(5) . ?
N1 C4 1.487(5) . ?
O1 C11 1.419(4) . ?
O1 B1 1.459(5) . ?
C1 N2 1.353(5) . ?
C1 B1 1.682(5) . ?
B1 O3 1.457(5) . ?
B1 O2 1.469(5) . ?
N2 C3 1.390(5) . ?
N2 C7 1.467(5) . ?
O2 C10 1.424(4) . ?
B2 O6 1.457(5) . ?
B2 O4 1.461(5) . ?
B2 O5 1.462(5) . ?
B2 C13 1.683(5) . ?
C2 C3 1.346(6) . ?
C2 H00P 0.9500 . ?
N4 C13 1.350(5) . ?
N4 C15 1.385(5) . ?
N4 C19 1.479(5) . ?
O4 C23 1.421(4) . ?
C4 C6 1.520(5) . ?
C4 C5 1.523(5) . ?
C4 H00Q 1.0000 . ?
C3 H00L 0.9500 . ?
O3 C12 1.414(4) . ?
N3 C13 1.352(5) . ?
N3 C14 1.384(5) . ?
N3 C16 1.479(5) . ?
C5 H00U 0.9800 . ?
C5 H00V 0.9800 . ?
C5 H00W 0.9800 . ?
O5 C22 1.420(4) . ?
C6 H01C 0.9800 . ?
C6 H01D 0.9800 . ?
C6 H01E 0.9800 . ?
O6 C24 1.410(4) . ?
C7 C9 1.505(6) . ?
C7 C8 1.508(5) . ?
C7 H00T 1.0000 . ?
C8 H01O 0.9800 . ?
C8 H01P 0.9800 . ?
C8 H01Q 0.9800 . ?
C9 H01R 0.9800 . ?
C9 H01S 0.9800 . ?
C9 H01T 0.9800 . ?
C20 C19 1.513(5) . ?
C20 H017 0.9800 . ?
C20 H018 0.9800 . ?
C20 H019 0.9800 . ?
C21 C19 1.525(5) . ?
C21 H00X 0.9800 . ?
C21 H00Y 0.9800 . ?
C21 H00Z 0.9800 . ?
C22 C23 1.521(6) . ?
C22 H22 0.9900 . ?
C22 H00K 0.9900 . ?
C23 H00F 0.9900 . ?
C23 H23 0.9900 . ?
C24 C24 1.505(7) 2_776 ?
C24 H00C 0.9900 . ?
C24 H00D 0.9900 . ?
C25 C26 1.377(6) . ?
C25 C30 1.381(7) . ?
C25 H01L 0.9500 . ?
C26 C27 1.374(6) . ?
C26 H01K 0.9500 . ?
C27 C28 1.370(6) . ?
C27 H01M 0.9500 . ?
C28 C29 1.394(7) . ?
C28 H010 0.9500 . ?
C29 C30 1.381(7) . ?
C29 H01F 0.9500 . ?
C30 H01B 0.9500 . ?
C32 C33 1.379(6) . ?
C32 C37 1.389(6) . ?
C32 H01N 0.9500 . ?
C33 C34 1.375(6) . ?
C33 H011 0.9500 . ?
C34 C35 1.378(6) . ?
C34 H012 0.9500 . ?
C35 C36 1.372(6) . ?
C35 H01A 0.9500 . ?
C36 C37 1.373(7) . ?
C36 H013 0.9500 . ?
C37 H01G 0.9500 . ?
C10 C11 1.513(6) . ?
C10 H00N 0.9900 . ?
C10 H00O 0.9900 . ?
C11 H00R 0.9900 . ?
C11 H00S 0.9900 . ?
C12 C12 1.514(7) 2_665 ?
C12 H00A 0.9900 . ?
C12 H00B 0.9900 . ?
C16 C18 1.515(6) . ?
C16 C17 1.524(5) . ?
C16 H16 1.0000 . ?
C15 C14 1.339(6) . ?
C15 H15 0.9500 . ?
C14 H00M 0.9500 . ?
C19 H19 1.0000 . ?
C18 H01H 0.9800 . ?
C18 H01I 0.9800 . ?
C18 H01J 0.9800 . ?
C17 H014 0.9800 . ?
C17 H015 0.9800 . ?
C17 H016 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
C1 N1 C2 110.3(3) . . ?
C1 N1 C4 126.2(3) . . ?
C2 N1 C4 123.4(3) . . ?
C11 O1 B1 107.7(3) . . ?
N2 C1 N1 105.5(3) . . ?
N2 C1 B1 122.6(3) . . ?
N1 C1 B1 131.5(3) . . ?
O3 B1 O1 110.6(3) . . ?
O3 B1 O2 111.7(3) . . ?
O1 B1 O2 107.1(3) . . ?
O3 B1 C1 109.2(3) . . ?
O1 B1 C1 106.2(3) . . ?
O2 B1 C1 111.9(3) . . ?
C1 N2 C3 110.2(3) . . ?
C1 N2 C7 125.3(3) . . ?
C3 N2 C7 124.4(3) . . ?
C10 O2 B1 105.8(3) . . ?
O6 B2 O4 111.1(3) . . ?
O6 B2 O5 112.3(3) . . ?
O4 B2 O5 106.7(3) . . ?
O6 B2 C13 108.5(3) . . ?
O4 B2 C13 105.9(3) . . ?
O5 B2 C13 112.3(3) . . ?
C3 C2 N1 107.0(3) . . ?
C3 C2 H00P 126.5 . . ?
N1 C2 H00P 126.5 . . ?
C13 N4 C15 109.9(3) . . ?
C13 N4 C19 125.8(3) . . ?
C15 N4 C19 124.3(3) . . ?
C23 O4 B2 107.7(3) . . ?
N1 C4 C6 109.7(3) . . ?
N1 C4 C5 110.2(3) . . ?
C6 C4 C5 112.3(3) . . ?
N1 C4 H00Q 108.2 . . ?
C6 C4 H00Q 108.2 . . ?
C5 C4 H00Q 108.2 . . ?
C2 C3 N2 106.9(3) . . ?
C2 C3 H00L 126.5 . . ?
N2 C3 H00L 126.5 . . ?
C12 O3 B1 117.9(3) . . ?
C13 N3 C14 110.3(3) . . ?
C13 N3 C16 125.1(3) . . ?
C14 N3 C16 124.6(3) . . ?
C4 C5 H00U 109.5 . . ?
C4 C5 H00V 109.5 . . ?
H00U C5 H00V 109.5 . . ?
C4 C5 H00W 109.5 . . ?
H00U C5 H00W 109.5 . . ?
H00V C5 H00W 109.5 . . ?
C22 O5 B2 106.6(3) . . ?
C4 C6 H01C 109.5 . . ?
C4 C6 H01D 109.5 . . ?
H01C C6 H01D 109.5 . . ?
C4 C6 H01E 109.5 . . ?
H01C C6 H01E 109.5 . . ?
H01D C6 H01E 109.5 . . ?
C24 O6 B2 116.3(3) . . ?
N2 C7 C9 110.8(3) . . ?
N2 C7 C8 110.0(3) . . ?
C9 C7 C8 112.2(4) . . ?
N2 C7 H00T 107.9 . . ?
C9 C7 H00T 107.9 . . ?
C8 C7 H00T 107.9 . . ?
C7 C8 H01O 109.5 . . ?
C7 C8 H01P 109.5 . . ?
H01O C8 H01P 109.5 . . ?
C7 C8 H01Q 109.5 . . ?
H01O C8 H01Q 109.5 . . ?
H01P C8 H01Q 109.5 . . ?
C7 C9 H01R 109.5 . . ?
C7 C9 H01S 109.5 . . ?
H01R C9 H01S 109.5 . . ?
C7 C9 H01T 109.5 . . ?
H01R C9 H01T 109.5 . . ?
H01S C9 H01T 109.5 . . ?
C19 C20 H017 109.5 . . ?
C19 C20 H018 109.5 . . ?
H017 C20 H018 109.5 . . ?
C19 C20 H019 109.5 . . ?
H017 C20 H019 109.5 . . ?
H018 C20 H019 109.5 . . ?
C19 C21 H00X 109.5 . . ?
C19 C21 H00Y 109.5 . . ?
H00X C21 H00Y 109.5 . . ?
C19 C21 H00Z 109.5 . . ?
H00X C21 H00Z 109.5 . . ?
H00Y C21 H00Z 109.5 . . ?
O5 C22 C23 104.0(3) . . ?
O5 C22 H22 110.9 . . ?
C23 C22 H22 110.9 . . ?
O5 C22 H00K 110.9 . . ?
C23 C22 H00K 110.9 . . ?
H22 C22 H00K 109.0 . . ?
O4 C23 C22 104.1(3) . . ?
O4 C23 H00F 110.9 . . ?
C22 C23 H00F 110.9 . . ?
O4 C23 H23 110.9 . . ?
C22 C23 H23 110.9 . . ?
H00F C23 H23 108.9 . . ?
O6 C24 C24 109.3(4) . 2_776 ?
O6 C24 H00C 109.8 . . ?
C24 C24 H00C 109.8 2_776 . ?
O6 C24 H00D 109.8 . . ?
C24 C24 H00D 109.8 2_776 . ?
H00C C24 H00D 108.3 . . ?
C26 C25 C30 120.2(4) . . ?
C26 C25 H01L 119.9 . . ?
C30 C25 H01L 119.9 . . ?
C27 C26 C25 120.0(4) . . ?
C27 C26 H01K 120.0 . . ?
C25 C26 H01K 120.0 . . ?
C28 C27 C26 120.4(4) . . ?
C28 C27 H01M 119.8 . . ?
C26 C27 H01M 119.8 . . ?
C27 C28 C29 120.0(4) . . ?
C27 C28 H010 120.0 . . ?
C29 C28 H010 120.0 . . ?
C30 C29 C28 119.5(4) . . ?
C30 C29 H01F 120.3 . . ?
C28 C29 H01F 120.3 . . ?
C29 C30 C25 119.9(4) . . ?
C29 C30 H01B 120.1 . . ?
C25 C30 H01B 120.1 . . ?
C33 C32 C37 120.2(4) . . ?
C33 C32 H01N 119.9 . . ?
C37 C32 H01N 119.9 . . ?
C34 C33 C32 120.0(4) . . ?
C34 C33 H011 120.0 . . ?
C32 C33 H011 120.0 . . ?
C33 C34 C35 119.4(4) . . ?
C33 C34 H012 120.3 . . ?
C35 C34 H012 120.3 . . ?
C36 C35 C34 121.0(4) . . ?
C36 C35 H01A 119.5 . . ?
C34 C35 H01A 119.5 . . ?
C35 C36 C37 119.9(4) . . ?
C35 C36 H013 120.1 . . ?
C37 C36 H013 120.1 . . ?
C36 C37 C32 119.5(4) . . ?
C36 C37 H01G 120.2 . . ?
C32 C37 H01G 120.2 . . ?
O2 C10 C11 104.9(3) . . ?
O2 C10 H00N 110.8 . . ?
C11 C10 H00N 110.8 . . ?
O2 C10 H00O 110.8 . . ?
C11 C10 H00O 110.8 . . ?
H00N C10 H00O 108.8 . . ?
O1 C11 C10 104.0(3) . . ?
O1 C11 H00R 111.0 . . ?
C10 C11 H00R 111.0 . . ?
O1 C11 H00S 111.0 . . ?
C10 C11 H00S 111.0 . . ?
H00R C11 H00S 109.0 . . ?
O3 C12 C12 109.4(4) . 2_665 ?
O3 C12 H00A 109.8 . . ?
C12 C12 H00A 109.8 2_665 . ?
O3 C12 H00B 109.8 . . ?
C12 C12 H00B 109.8 2_665 . ?
H00A C12 H00B 108.2 . . ?
N4 C13 N3 105.6(3) . . ?
N4 C13 B2 131.3(3) . . ?
N3 C13 B2 122.7(3) . . ?
N3 C16 C18 110.8(3) . . ?
N3 C16 C17 108.9(3) . . ?
C18 C16 C17 112.7(3) . . ?
N3 C16 H16 108.1 . . ?
C18 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
C14 C15 N4 107.4(3) . . ?
C14 C15 H15 126.3 . . ?
N4 C15 H15 126.3 . . ?
C15 C14 N3 106.7(3) . . ?
C15 C14 H00M 126.6 . . ?
N3 C14 H00M 126.6 . . ?
N4 C19 C20 110.1(3) . . ?
N4 C19 C21 110.4(3) . . ?
C20 C19 C21 111.7(3) . . ?
N4 C19 H19 108.2 . . ?
C20 C19 H19 108.2 . . ?
C21 C19 H19 108.2 . . ?
C16 C18 H01H 109.5 . . ?
C16 C18 H01I 109.5 . . ?
H01H C18 H01I 109.5 . . ?
C16 C18 H01J 109.5 . . ?
H01H C18 H01J 109.5 . . ?
H01I C18 H01J 109.5 . . ?
C16 C17 H014 109.5 . . ?
C16 C17 H015 109.5 . . ?
H014 C17 H015 109.5 . . ?
C16 C17 H016 109.5 . . ?
H014 C17 H016 109.5 . . ?
H015 C17 H016 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.1(4) . . . . ?
C4 N1 C1 N2 -177.8(3) . . . . ?
C2 N1 C1 B1 -173.5(4) . . . . ?
C4 N1 C1 B1 8.9(6) . . . . ?
C11 O1 B1 O3 115.1(3) . . . . ?
C11 O1 B1 O2 -6.8(4) . . . . ?
C11 O1 B1 C1 -126.5(3) . . . . ?
N2 C1 B1 O3 62.3(4) . . . . ?
N1 C1 B1 O3 -125.3(4) . . . . ?
N2 C1 B1 O1 -57.0(4) . . . . ?
N1 C1 B1 O1 115.4(4) . . . . ?
N2 C1 B1 O2 -173.5(3) . . . . ?
N1 C1 B1 O2 -1.1(5) . . . . ?
N1 C1 N2 C3 -0.6(4) . . . . ?
B1 C1 N2 C3 173.5(3) . . . . ?
N1 C1 N2 C7 -178.4(3) . . . . ?
B1 C1 N2 C7 -4.4(5) . . . . ?
O3 B1 O2 C10 -135.6(3) . . . . ?
O1 B1 O2 C10 -14.3(4) . . . . ?
C1 B1 O2 C10 101.6(3) . . . . ?
C1 N1 C2 C3 0.8(4) . . . . ?
C4 N1 C2 C3 178.6(3) . . . . ?
O6 B2 O4 C23 117.3(3) . . . . ?
O5 B2 O4 C23 -5.3(4) . . . . ?
C13 B2 O4 C23 -125.1(3) . . . . ?
C1 N1 C4 C6 112.4(4) . . . . ?
C2 N1 C4 C6 -65.0(4) . . . . ?
C1 N1 C4 C5 -123.5(4) . . . . ?
C2 N1 C4 C5 59.2(4) . . . . ?
N1 C2 C3 N2 -1.1(4) . . . . ?
C1 N2 C3 C2 1.1(4) . . . . ?
C7 N2 C3 C2 179.0(3) . . . . ?
O1 B1 O3 C12 -178.8(3) . . . . ?
O2 B1 O3 C12 -59.6(4) . . . . ?
C1 B1 O3 C12 64.7(4) . . . . ?
O6 B2 O5 C22 -138.0(3) . . . . ?
O4 B2 O5 C22 -16.1(4) . . . . ?
C13 B2 O5 C22 99.5(3) . . . . ?
O4 B2 O6 C24 179.2(3) . . . . ?
O5 B2 O6 C24 -61.4(4) . . . . ?
C13 B2 O6 C24 63.2(4) . . . . ?
C1 N2 C7 C9 117.5(4) . . . . ?
C3 N2 C7 C9 -60.1(5) . . . . ?
C1 N2 C7 C8 -117.8(4) . . . . ?
C3 N2 C7 C8 64.6(5) . . . . ?
B2 O5 C22 C23 29.7(4) . . . . ?
B2 O4 C23 C22 23.0(4) . . . . ?
O5 C22 C23 O4 -32.8(4) . . . . ?
B2 O6 C24 C24 -168.6(4) . . . 2_776 ?
C30 C25 C26 C27 -0.5(7) . . . . ?
C25 C26 C27 C28 -0.8(6) . . . . ?
C26 C27 C28 C29 0.8(6) . . . . ?
C27 C28 C29 C30 0.4(6) . . . . ?
C28 C29 C30 C25 -1.6(6) . . . . ?
C26 C25 C30 C29 1.7(7) . . . . ?
C37 C32 C33 C34 0.1(6) . . . . ?
C32 C33 C34 C35 -0.3(6) . . . . ?
C33 C34 C35 C36 0.5(6) . . . . ?
C34 C35 C36 C37 -0.5(7) . . . . ?
C35 C36 C37 C32 0.2(7) . . . . ?
C33 C32 C37 C36 0.0(6) . . . . ?
B1 O2 C10 C11 28.6(4) . . . . ?
B1 O1 C11 C10 23.8(4) . . . . ?
O2 C10 C11 O1 -32.9(4) . . . . ?
B1 O3 C12 C12 -177.6(3) . . . 2_665 ?
C15 N4 C13 N3 -0.1(4) . . . . ?
C19 N4 C13 N3 -176.8(3) . . . . ?
C15 N4 C13 B2 -173.3(4) . . . . ?
C19 N4 C13 B2 10.0(6) . . . . ?
C14 N3 C13 N4 -0.7(4) . . . . ?
C16 N3 C13 N4 -179.9(3) . . . . ?
C14 N3 C13 B2 173.3(3) . . . . ?
C16 N3 C13 B2 -6.0(5) . . . . ?
O6 B2 C13 N4 -126.6(4) . . . . ?
O4 B2 C13 N4 114.1(4) . . . . ?
O5 B2 C13 N4 -1.9(6) . . . . ?
O6 B2 C13 N3 61.2(4) . . . . ?
O4 B2 C13 N3 -58.1(4) . . . . ?
O5 B2 C13 N3 -174.1(3) . . . . ?
C13 N3 C16 C18 111.7(4) . . . . ?
C14 N3 C16 C18 -67.4(4) . . . . ?
C13 N3 C16 C17 -123.9(4) . . . . ?
C14 N3 C16 C17 57.0(5) . . . . ?
C13 N4 C15 C14 0.8(4) . . . . ?
C19 N4 C15 C14 177.6(3) . . . . ?
N4 C15 C14 N3 -1.2(4) . . . . ?
C13 N3 C14 C15 1.2(4) . . . . ?
C16 N3 C14 C15 -179.6(3) . . . . ?
C13 N4 C19 C20 114.5(4) . . . . ?
C15 N4 C19 C20 -61.8(5) . . . . ?
C13 N4 C19 C21 -121.7(4) . . . . ?
C15 N4 C19 C21 62.0(4) . . . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

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

data_ae141_a
_database_code_depnum_ccdc_archive 'CCDC 1529578'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C20.88 H39.63 B2 N2 O4, C21 H40 B2 N2 O4, 0.123(C H3)'
_chemical_formula_sum            'C42 H80 B4 N4 O8'

_chemical_formula_weight         812.34

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   19.0612(13)
_cell_length_b                   15.4007(10)
_cell_length_c                   17.5352(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.309(2)
_cell_angle_gamma                90
_cell_volume                     4887.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      2.319
_cell_measurement_theta_max      25.998

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63152
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.736
_diffrn_reflns_theta_max         26.056
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9644
_reflns_number_gt                7864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0589P)²+3.7685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9644
_refine_ls_number_parameters     653
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.041
_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
O1 O 1.01126(6) 0.61987(7) 0.81880(6) 0.0147(2) Uani 1 1 d . . . . .
N1 N 1.06118(7) 0.75538(9) 0.71294(8) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.99434(9) 0.75466(10) 0.72444(8) 0.0146(3) Uani 1 1 d . . . . .
B1 B 0.95403(10) 0.67359(11) 0.76008(10) 0.0154(3) Uani 1 1 d . . . . .
O2 O 0.91261(6) 0.71640(7) 0.80876(6) 0.0175(2) Uani 1 1 d . . . . .
N2 N 0.96745(7) 0.83581(8) 0.70567(8) 0.0164(3) Uani 1 1 d . . . . .
C2 C 1.07609(9) 0.83710(11) 0.68880(10) 0.0215(4) Uani 1 1 d . . . . .
H2 H 1.1196 0.8542 0.6772 0.026 Uiso 1 1 calc R U . . .
B2 B 0.90109(10) 0.60990(11) 0.68141(11) 0.0161(3) Uani 1 1 d . . . . .
N3 N 0.48987(8) 0.85871(9) 0.22299(8) 0.0216(3) Uani 1 1 d . . . . .
C3 C 1.01786(9) 0.88740(11) 0.68481(10) 0.0200(3) Uani 1 1 d . . . . .
H3 H 1.0122 0.9471 0.6704 0.024 Uiso 1 1 calc R U . . .
B3 B 0.51835(10) 0.68789(12) 0.20015(11) 0.0190(4) Uani 1 1 d . . . . .
N4 N 0.48450(8) 0.77589(9) 0.31953(8) 0.0236(3) Uani 1 1 d . . . . .
C4 C 1.10901(10) 0.67840(11) 0.71801(10) 0.0236(4) Uani 1 1 d . . . . .
H4 H 1.0925 0.6321 0.7485 0.028 Uiso 1 1 calc R U . . .
B4 B 0.43222(11) 0.64563(13) 0.14946(11) 0.0207(4) Uani 1 1 d . . . . .
O5 O 0.56211(6) 0.71945(8) 0.14934(7) 0.0230(3) Uani 1 1 d . . . . .
C5 C 1.18914(11) 0.69977(14) 0.76301(11) 0.0350(5) Uani 1 1 d . . . . .
H5A H 1.2188 0.6466 0.7711 0.053 Uiso 1 1 calc R U . . .
H5B H 1.1926 0.7252 0.8153 0.053 Uiso 1 1 calc R U . . .
H5C H 1.2078 0.7414 0.7317 0.053 Uiso 1 1 calc R U . . .
O6 O 0.56774(6) 0.62584(7) 0.25721(7) 0.0207(3) Uani 1 1 d . . . . .
C6 C 1.09933(11) 0.64444(13) 0.63370(11) 0.0302(4) Uani 1 1 d . . . . .
H6A H 1.1283 0.5912 0.6371 0.045 Uiso 1 1 calc R U . . .
H6B H 1.1165 0.6883 0.6032 0.045 Uiso 1 1 calc R U . . .
H6C H 1.0470 0.6320 0.6065 0.045 Uiso 1 1 calc R U . . .
O7 O 0.39259(7) 0.66632(9) 0.07144(7) 0.0305(3) Uani 1 1 d . . . . .
O8 O 0.39155(6) 0.59440(8) 0.18436(7) 0.0243(3) Uani 1 1 d . . . . .
C10 C 1.01716(9) 0.65292(10) 0.89707(9) 0.0160(3) Uani 1 1 d . . . . .
C11 C 1.06973(10) 0.73089(11) 0.91561(10) 0.0223(4) Uani 1 1 d . . . . .
H11A H 1.0782 0.7495 0.9712 0.033 Uiso 1 1 calc R U . . .
H11B H 1.0477 0.7787 0.8791 0.033 Uiso 1 1 calc R U . . .
H11C H 1.1169 0.7143 0.9084 0.033 Uiso 1 1 calc R U . . .
C12 C 1.04870(10) 0.58260(11) 0.95920(9) 0.0209(3) Uani 1 1 d . . . . .
H12A H 1.0473 0.6023 1.0119 0.031 Uiso 1 1 calc R U . . .
H12B H 1.0999 0.5706 0.9619 0.031 Uiso 1 1 calc R U . . .
H12C H 1.0192 0.5296 0.9439 0.031 Uiso 1 1 calc R U . . .
C13 C 0.93642(9) 0.67938(10) 0.88744(9) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.92858(11) 0.74702(12) 0.94753(11) 0.0286(4) Uani 1 1 d . . . . .
H14A H 0.9505 0.7247 1.0022 0.043 Uiso 1 1 calc R U . . .
H14B H 0.8761 0.7595 0.9380 0.043 Uiso 1 1 calc R U . . .
H14C H 0.9541 0.8004 0.9410 0.043 Uiso 1 1 calc R U . . .
C15 C 0.88706(9) 0.60125(11) 0.88861(10) 0.0211(3) Uani 1 1 d . . . . .
H15A H 0.9008 0.5772 0.9431 0.032 Uiso 1 1 calc R U . . .
H15B H 0.8935 0.5568 0.8514 0.032 Uiso 1 1 calc R U . . .
H15J H 0.8353 0.6198 0.8721 0.032 Uiso 1 1 calc R U . . .
C22 C 0.49900(9) 0.77524(11) 0.24867(10) 0.0201(3) Uani 1 1 d . . . . .
C23 C 0.47387(10) 0.91156(11) 0.27950(10) 0.0232(4) Uani 1 1 d . . . . .
H23 H 0.4670 0.9727 0.2763 0.028 Uiso 1 1 calc R U . . .
C24 C 0.46993(10) 0.85974(11) 0.33935(10) 0.0250(4) Uani 1 1 d . . . . .
H24 H 0.4592 0.8771 0.3865 0.030 Uiso 1 1 calc R U . . .
C25 C 0.49453(11) 0.89036(11) 0.14484(10) 0.0257(4) Uani 1 1 d . . . . .
H25 H 0.4957 0.8388 0.1106 0.031 Uiso 1 1 calc R U . . .
C26 C 0.56544(11) 0.94089(13) 0.15814(12) 0.0331(4) Uani 1 1 d . . . . .
H26A H 0.5686 0.9612 0.1063 0.050 Uiso 1 1 calc R U . . .
H26B H 0.6077 0.9033 0.1839 0.050 Uiso 1 1 calc R U . . .
H26C H 0.5659 0.9909 0.1928 0.050 Uiso 1 1 calc R U . . .
C27 C 0.42638(12) 0.94417(13) 0.10225(11) 0.0333(4) Uani 1 1 d . . . . .
H27A H 0.4269 0.9588 0.0481 0.050 Uiso 1 1 calc R U . . .
H27B H 0.4266 0.9977 0.1326 0.050 Uiso 1 1 calc R U . . .
H27C H 0.3818 0.9106 0.0987 0.050 Uiso 1 1 calc R U . . .
C28 C 0.48005(12) 0.69793(12) 0.36755(11) 0.0313(4) Uani 1 1 d . . . . .
H28 H 0.4902 0.6458 0.3387 0.038 Uiso 1 1 calc R U . . .
C29 C 0.53759(14) 0.70120(17) 0.44899(13) 0.0499(6) Uani 1 1 d . . . . .
H29A H 0.5381 0.6459 0.4768 0.075 Uiso 1 1 calc R U . . .
H29B H 0.5259 0.7484 0.4805 0.075 Uiso 1 1 calc R U . . .
H29C H 0.5863 0.7114 0.4428 0.075 Uiso 1 1 calc R U . . .
C30 C 0.40319(13) 0.68928(14) 0.37298(14) 0.0423(5) Uani 1 1 d . . . . .
H30A H 0.3990 0.6345 0.3997 0.063 Uiso 1 1 calc R U . . .
H30B H 0.3674 0.6897 0.3188 0.063 Uiso 1 1 calc R U . . .
H30C H 0.3930 0.7380 0.4039 0.063 Uiso 1 1 calc R U . . .
C31 C 0.62774(10) 0.66857(12) 0.16705(13) 0.0297(4) Uani 1 1 d . . . . .
C32 C 0.68888(12) 0.72430(15) 0.15317(17) 0.0483(6) Uani 1 1 d . . . . .
H32A H 0.7360 0.6930 0.1720 0.072 Uiso 1 1 calc R U . . .
H32B H 0.6929 0.7789 0.1829 0.072 Uiso 1 1 calc R U . . .
H32C H 0.6771 0.7367 0.0957 0.072 Uiso 1 1 calc R U . . .
C33 C 0.61194(14) 0.59060(13) 0.11026(14) 0.0419(5) Uani 1 1 d . . . . .
H33A H 0.6575 0.5572 0.1184 0.063 Uiso 1 1 calc R U . . .
H33B H 0.5938 0.6110 0.0546 0.063 Uiso 1 1 calc R U . . .
H33C H 0.5745 0.5536 0.1214 0.063 Uiso 1 1 calc R U . . .
C34 C 0.64124(10) 0.64174(12) 0.25565(12) 0.0288(4) Uani 1 1 d . . . . .
C35 C 0.68702(11) 0.55907(14) 0.28141(15) 0.0405(5) Uani 1 1 d . . . . .
H35A H 0.7368 0.5684 0.2780 0.061 Uiso 1 1 calc R U . . .
H35B H 0.6633 0.5111 0.2459 0.061 Uiso 1 1 calc R U . . .
H35C H 0.6903 0.5447 0.3369 0.061 Uiso 1 1 calc R U . . .
C36 C 0.67636(11) 0.71491(14) 0.31463(14) 0.0419(5) Uani 1 1 d . . . . .
H36A H 0.7276 0.7235 0.3157 0.063 Uiso 1 1 calc R U . . .
H36B H 0.6754 0.6993 0.3685 0.063 Uiso 1 1 calc R U . . .
H36C H 0.6484 0.7687 0.2974 0.063 Uiso 1 1 calc R U . . .
C37 C 0.31655(10) 0.63995(13) 0.05764(11) 0.0299(4) Uani 1 1 d . . . . .
C38 C 0.27533(12) 0.72010(15) 0.07279(15) 0.0467(6) Uani 1 1 d . . . . .
H38A H 0.2230 0.7058 0.0621 0.070 Uiso 1 1 calc R U . . .
H38B H 0.2799 0.7672 0.0371 0.070 Uiso 1 1 calc R U . . .
H38C H 0.2967 0.7385 0.1288 0.070 Uiso 1 1 calc R U . . .
C39 C 0.28464(12) 0.61033(18) -0.02902(13) 0.0468(6) Uani 1 1 d . . . . .
H39A H 0.2347 0.5875 -0.0381 0.070 Uiso 1 1 calc R U . . .
H39B H 0.3161 0.5648 -0.0399 0.070 Uiso 1 1 calc R U . . .
H39C H 0.2826 0.6597 -0.0650 0.070 Uiso 1 1 calc R U . . .
C40 C 0.32403(10) 0.56846(12) 0.12165(11) 0.0269(4) Uani 1 1 d . . . . .
C41 C 0.33740(12) 0.47795(14) 0.09310(14) 0.0423(5) Uani 1 1 d . . . . .
H41A H 0.2923 0.4573 0.0527 0.063 Uiso 1 1 calc R U . . .
H41B H 0.3509 0.4379 0.1389 0.063 Uiso 1 1 calc R U . . .
H41C H 0.3776 0.4806 0.0694 0.063 Uiso 1 1 calc R U . . .
C42 C 0.26191(11) 0.56419(16) 0.15830(14) 0.0415(5) Uani 1 1 d . . . . .
H42A H 0.2151 0.5533 0.1159 0.062 Uiso 1 1 calc R U . . .
H42B H 0.2589 0.6194 0.1848 0.062 Uiso 1 1 calc R U . . .
H42C H 0.2716 0.5171 0.1978 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8913(3) 0.8618(3) 0.6948(3) 0.0231(7) Uani 0.743(5) 1 d . U P A 1
H7 H 0.8666 0.8140 0.7153 0.028 Uiso 0.743(5) 1 calc R U P A 1
C8 C 0.89059(17) 0.94197(19) 0.7437(2) 0.0349(7) Uani 0.743(5) 1 d . U P A 1
H8A H 0.8394 0.9600 0.7352 0.052 Uiso 0.743(5) 1 calc R U P A 1
H8B H 0.9174 0.9888 0.7269 0.052 Uiso 0.743(5) 1 calc R U P A 1
H8C H 0.9145 0.9293 0.8007 0.052 Uiso 0.743(5) 1 calc R U P A 1
C9 C 0.84992(15) 0.8746(2) 0.60590(17) 0.0325(7) Uani 0.743(5) 1 d . U P A 1
H9A H 0.7984 0.8898 0.5990 0.049 Uiso 0.743(5) 1 calc R U P A 1
H9B H 0.8516 0.8207 0.5768 0.049 Uiso 0.743(5) 1 calc R U P A 1
H9C H 0.8732 0.9214 0.5846 0.049 Uiso 0.743(5) 1 calc R U P A 1
O3 O 0.90583(10) 0.61071(10) 0.60403(9) 0.0210(3) Uani 0.877(3) 1 d . U P B 3
O4 O 0.85022(11) 0.54890(15) 0.68799(13) 0.0316(5) Uani 0.877(3) 1 d . U P B 3
C16 C 0.86569(13) 0.53546(13) 0.56188(11) 0.0210(5) Uani 0.877(3) 1 d . . P B 3
C17 C 0.92373(14) 0.46384(16) 0.57104(16) 0.0376(6) Uani 0.877(3) 1 d . . P B 3
H17A H 0.9636 0.4853 0.5519 0.056 Uiso 0.877(3) 1 calc R U P B 3
H17B H 0.9006 0.4131 0.5394 0.056 Uiso 0.877(3) 1 calc R U P B 3
H17C H 0.9440 0.4474 0.6277 0.056 Uiso 0.877(3) 1 calc R U P B 3
C18 C 0.83477(17) 0.55493(16) 0.47380(13) 0.0386(6) Uani 0.877(3) 1 d . . P B 3
H18A H 0.8754 0.5645 0.4517 0.058 Uiso 0.877(3) 1 calc R U P B 3
H18B H 0.8040 0.6072 0.4659 0.058 Uiso 0.877(3) 1 calc R U P B 3
H18C H 0.8047 0.5058 0.4462 0.058 Uiso 0.877(3) 1 calc R U P B 3
C19 C 0.81284(14) 0.51364(18) 0.61086(19) 0.0255(7) Uani 0.877(3) 1 d . . P B 3
C20 C 0.7949(3) 0.4210(3) 0.6124(2) 0.0530(13) Uani 0.877(3) 1 d . . P B 3
H20A H 0.7594 0.4131 0.6420 0.079 Uiso 0.877(3) 1 calc R U P B 3
H20B H 0.8400 0.3882 0.6390 0.079 Uiso 0.877(3) 1 calc R U P B 3
H20C H 0.7732 0.3998 0.5573 0.079 Uiso 0.877(3) 1 calc R U P B 3
C21 C 0.74049(15) 0.5702(2) 0.5755(3) 0.0666(12) Uani 0.877(3) 1 d . . P B 3
H21A H 0.7109 0.5679 0.6122 0.100 Uiso 0.877(3) 1 calc R U P B 3
H21B H 0.7115 0.5472 0.5230 0.100 Uiso 0.877(3) 1 calc R U P B 3
H21C H 0.7543 0.6305 0.5695 0.100 Uiso 0.877(3) 1 calc R U P B 3
C227 C 0.8930(11) 0.8718(12) 0.7109(9) 0.0269(10) Uani 0.257(5) 1 d . U P A 2
H27 H 0.8608 0.8227 0.7169 0.032 Uiso 0.257(5) 1 calc R U P A 2
C228 C 0.9106(5) 0.9323(6) 0.7861(6) 0.0307(12) Uani 0.257(5) 1 d . U P A 2
H28A H 0.8645 0.9565 0.7905 0.046 Uiso 0.257(5) 1 calc R U P A 2
H28B H 0.9429 0.9797 0.7805 0.046 Uiso 0.257(5) 1 calc R U P A 2
H28C H 0.9354 0.8987 0.8345 0.046 Uiso 0.257(5) 1 calc R U P A 2
C229 C 0.8558(4) 0.9206(6) 0.6360(6) 0.0345(11) Uani 0.257(5) 1 d . U P A 2
H29X H 0.8053 0.9354 0.6344 0.052 Uiso 0.257(5) 1 calc R U P A 2
H29Y H 0.8541 0.8846 0.5894 0.052 Uiso 0.257(5) 1 calc R U P A 2
H29Z H 0.8834 0.9740 0.6348 0.052 Uiso 0.257(5) 1 calc R U P A 2
O43 O 0.8767(8) 0.6302(8) 0.6059(7) 0.0241(10) Uani 0.123(3) 1 d . U P B 4
O44 O 0.8746(9) 0.5326(13) 0.6957(12) 0.0309(11) Uani 0.123(3) 1 d . U P B 4
C416 C 0.8298(10) 0.5635(11) 0.5599(9) 0.0259(9) Uani 0.123(3) 1 d . U P B 4
C417 C 0.8900(10) 0.5070(12) 0.5316(11) 0.034(2) Uani 0.123(3) 1 d . U P B 4
H41X H 0.9058 0.5404 0.4924 0.051 Uiso 0.123(3) 1 calc R U P B 4
H41Y H 0.8672 0.4525 0.5071 0.051 Uiso 0.123(3) 1 calc R U P B 4
H41Z H 0.9329 0.4942 0.5784 0.051 Uiso 0.123(3) 1 calc R U P B 4
C418 C 0.7909(10) 0.5761(11) 0.4833(9) 0.031(2) Uani 0.123(3) 1 d . U P B 4
H41D H 0.8216 0.6056 0.4559 0.047 Uiso 0.123(3) 1 calc R U P B 4
H41E H 0.7475 0.6119 0.4801 0.047 Uiso 0.123(3) 1 calc R U P B 4
H41F H 0.7747 0.5199 0.4575 0.047 Uiso 0.123(3) 1 calc R U P B 4
C419 C 0.7967(16) 0.5321(17) 0.5993(16) 0.0289(9) Uani 0.123(3) 1 d . U P B 4
C420 C 0.7396(12) 0.5365(15) 0.6310(17) 0.054(6) Uani 0.123(3) 1 d . . P B 4
H42X H 0.7569 0.5176 0.6872 0.081 Uiso 0.123(3) 1 calc R U P B 4
H42Y H 0.6993 0.4986 0.6003 0.081 Uiso 0.123(3) 1 calc R U P B 4
H42Z H 0.7217 0.5965 0.6281 0.081 Uiso 0.123(3) 1 calc R U P B 4
C421 C 0.8022(18) 0.408(2) 0.6290(18) 0.026(2) Uani 0.123(3) 1 d . U P B 4
H42D H 0.7700 0.3965 0.6619 0.038 Uiso 0.123(3) 1 calc R U P B 4
H42E H 0.7860 0.3723 0.5801 0.038 Uiso 0.123(3) 1 calc R U P B 4
H42F H 0.8533 0.3927 0.6596 0.038 Uiso 0.123(3) 1 calc R U P B 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.4347(17) . ?
O1 B1 1.493(2) . ?
N1 C1 1.351(2) . ?
N1 C2 1.386(2) . ?
N1 C4 1.481(2) . ?
C1 N2 1.352(2) . ?
C1 B1 1.686(2) . ?
B1 O2 1.487(2) . ?
B1 B2 1.735(2) . ?
O2 C13 1.4285(18) . ?
N2 C3 1.382(2) . ?
N2 C7 1.459(6) . ?
N2 C227 1.554(19) . ?
C2 C3 1.337(2) . ?
C2 H2 0.9500 . ?
B2 O43 1.297(13) . ?
B2 O44 1.346(19) . ?
B2 O4 1.381(3) . ?
B2 O3 1.388(2) . ?
N3 C22 1.355(2) . ?
N3 C23 1.388(2) . ?
N3 C25 1.483(2) . ?
C3 H3 0.9500 . ?
B3 O5 1.481(2) . ?
B3 O6 1.486(2) . ?
B3 C22 1.693(2) . ?
B3 B4 1.730(3) . ?
N4 C22 1.355(2) . ?
N4 C24 1.388(2) . ?
N4 C28 1.484(2) . ?
C4 C5 1.519(3) . ?
C4 C6 1.524(2) . ?
C4 H4 1.0000 . ?
B4 O7 1.376(2) . ?
B4 O8 1.377(2) . ?
O5 C31 1.425(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O6 C34 1.431(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O7 C37 1.450(2) . ?
O8 C40 1.461(2) . ?
C10 C12 1.520(2) . ?
C10 C11 1.532(2) . ?
C10 C13 1.549(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.522(2) . ?
C13 C15 1.532(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15J 0.9800 . ?
C23 C24 1.339(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.513(3) . ?
C25 C27 1.524(3) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.504(3) . ?
C28 C30 1.504(3) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.527(3) . ?
C31 C33 1.528(3) . ?
C31 C34 1.549(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.529(3) . ?
C34 C36 1.534(3) . ?
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 C39 1.519(3) . ?
C37 C38 1.531(3) . ?
C37 C40 1.547(3) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C42 1.516(3) . ?
C40 C41 1.529(3) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C7 C8 1.505(5) . ?
C7 C9 1.523(5) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O3 C16 1.456(2) . ?
O4 C19 1.423(4) . ?
C16 C18 1.500(3) . ?
C16 C17 1.535(3) . ?
C16 C19 1.552(4) . ?
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 C20 1.470(5) . ?
C19 C21 1.584(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C227 C229 1.485(18) . ?
C227 C228 1.563(16) . ?
C227 H27 1.0000 . ?
C228 H28A 0.9800 . ?
C228 H28B 0.9800 . ?
C228 H28C 0.9800 . ?
C229 H29X 0.9800 . ?
C229 H29Y 0.9800 . ?
C229 H29Z 0.9800 . ?
O43 C416 1.432(19) . ?
O44 C419 1.87(3) . ?
C416 C419 1.18(3) . ?
C416 C418 1.33(2) . ?
C416 C417 1.64(3) . ?
C417 H41X 0.9800 . ?
C417 H41Y 0.9800 . ?
C417 H41Z 0.9800 . ?
C418 H41D 0.9800 . ?
C418 H41E 0.9800 . ?
C418 H41F 0.9800 . ?
C419 C420 1.37(3) . ?
C419 C421 1.98(4) . ?
C420 H42X 0.9800 . ?
C420 H42Y 0.9800 . ?
C420 H42Z 0.9800 . ?
C421 H42D 0.9800 . ?
C421 H42E 0.9800 . ?
C421 H42F 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
C10 O1 B1 106.50(11) . . ?
C1 N1 C2 110.28(13) . . ?
C1 N1 C4 125.17(13) . . ?
C2 N1 C4 124.33(13) . . ?
N1 C1 N2 105.04(13) . . ?
N1 C1 B1 128.49(14) . . ?
N2 C1 B1 126.36(14) . . ?
O2 B1 O1 104.74(12) . . ?
O2 B1 C1 105.70(12) . . ?
O1 B1 C1 110.29(13) . . ?
O2 B1 B2 115.23(13) . . ?
O1 B1 B2 110.59(12) . . ?
C1 B1 B2 110.06(12) . . ?
C13 O2 B1 108.22(12) . . ?
C1 N2 C3 110.73(13) . . ?
C1 N2 C7 124.8(3) . . ?
C3 N2 C7 123.6(3) . . ?
C1 N2 C227 126.8(7) . . ?
C3 N2 C227 122.3(7) . . ?
C3 C2 N1 107.19(14) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
O43 B2 O44 111.6(10) . . ?
O4 B2 O3 110.54(16) . . ?
O43 B2 B1 127.5(6) . . ?
O44 B2 B1 120.7(8) . . ?
O4 B2 B1 124.52(16) . . ?
O3 B2 B1 124.90(14) . . ?
C22 N3 C23 110.68(14) . . ?
C22 N3 C25 125.45(14) . . ?
C23 N3 C25 123.86(14) . . ?
C2 C3 N2 106.74(14) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
O5 B3 O6 104.99(13) . . ?
O5 B3 C22 107.11(13) . . ?
O6 B3 C22 111.38(13) . . ?
O5 B3 B4 115.94(14) . . ?
O6 B3 B4 113.72(13) . . ?
C22 B3 B4 103.64(13) . . ?
C22 N4 C24 110.55(14) . . ?
C22 N4 C28 125.37(14) . . ?
C24 N4 C28 123.99(14) . . ?
N1 C4 C5 110.93(15) . . ?
N1 C4 C6 109.38(14) . . ?
C5 C4 C6 111.97(15) . . ?
N1 C4 H4 108.1 . . ?
C5 C4 H4 108.1 . . ?
C6 C4 H4 108.1 . . ?
O7 B4 O8 111.38(15) . . ?
O7 B4 B3 124.03(15) . . ?
O8 B4 B3 124.27(15) . . ?
C31 O5 B3 108.07(13) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C34 O6 B3 107.10(13) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
B4 O7 C37 107.98(14) . . ?
B4 O8 C40 107.93(13) . . ?
O1 C10 C12 109.11(12) . . ?
O1 C10 C11 109.31(12) . . ?
C12 C10 C11 108.75(13) . . ?
O1 C10 C13 102.26(12) . . ?
C12 C10 C13 114.92(13) . . ?
C11 C10 C13 112.22(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 108.97(13) . . ?
O2 C13 C15 108.45(13) . . ?
C14 C13 C15 109.51(13) . . ?
O2 C13 C10 102.33(12) . . ?
C14 C13 C10 114.50(14) . . ?
C15 C13 C10 112.67(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15J 109.5 . . ?
H15A C15 H15J 109.5 . . ?
H15B C15 H15J 109.5 . . ?
N3 C22 N4 104.82(14) . . ?
N3 C22 B3 127.76(14) . . ?
N4 C22 B3 127.29(14) . . ?
C24 C23 N3 106.80(15) . . ?
C24 C23 H23 126.6 . . ?
N3 C23 H23 126.6 . . ?
C23 C24 N4 107.06(15) . . ?
C23 C24 H24 126.5 . . ?
N4 C24 H24 126.5 . . ?
N3 C25 C26 109.66(15) . . ?
N3 C25 C27 110.02(15) . . ?
C26 C25 C27 112.24(15) . . ?
N3 C25 H25 108.3 . . ?
C26 C25 H25 108.3 . . ?
C27 C25 H25 108.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N4 C28 C29 110.92(17) . . ?
N4 C28 C30 109.76(16) . . ?
C29 C28 C30 112.17(17) . . ?
N4 C28 H28 107.9 . . ?
C29 C28 H28 107.9 . . ?
C30 C28 H28 107.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O5 C31 C32 108.53(15) . . ?
O5 C31 C33 108.08(16) . . ?
C32 C31 C33 109.98(18) . . ?
O5 C31 C34 102.89(14) . . ?
C32 C31 C34 114.52(18) . . ?
C33 C31 C34 112.37(16) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O6 C34 C35 108.85(15) . . ?
O6 C34 C36 109.60(16) . . ?
C35 C34 C36 108.96(17) . . ?
O6 C34 C31 102.10(14) . . ?
C35 C34 C31 114.70(17) . . ?
C36 C34 C31 112.35(16) . . ?
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 . . ?
O7 C37 C39 108.43(16) . . ?
O7 C37 C38 106.60(16) . . ?
C39 C37 C38 110.48(17) . . ?
O7 C37 C40 102.63(14) . . ?
C39 C37 C40 115.41(18) . . ?
C38 C37 C40 112.54(17) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O8 C40 C42 108.26(15) . . ?
O8 C40 C41 107.31(15) . . ?
C42 C40 C41 109.39(17) . . ?
O8 C40 C37 102.14(14) . . ?
C42 C40 C37 115.62(17) . . ?
C41 C40 C37 113.46(16) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N2 C7 C8 109.7(3) . . ?
N2 C7 C9 110.1(3) . . ?
C8 C7 C9 112.5(4) . . ?
N2 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C9 C7 H7 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
B2 O3 C16 107.69(14) . . ?
B2 O4 C19 109.6(2) . . ?
O3 C16 C18 109.72(16) . . ?
O3 C16 C17 105.81(17) . . ?
C18 C16 C17 106.8(2) . . ?
O3 C16 C19 102.73(18) . . ?
C18 C16 C19 120.0(2) . . ?
C17 C16 C19 111.00(18) . . ?
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 . . ?
O4 C19 C20 113.8(3) . . ?
O4 C19 C16 103.0(2) . . ?
C20 C19 C16 114.6(3) . . ?
O4 C19 C21 106.0(2) . . ?
C20 C19 C21 111.2(3) . . ?
C16 C19 C21 107.5(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C229 C227 N2 108.6(11) . . ?
C229 C227 C228 111.2(13) . . ?
N2 C227 C228 107.7(11) . . ?
C229 C227 H27 109.7 . . ?
N2 C227 H27 109.7 . . ?
C228 C227 H27 109.7 . . ?
C227 C228 H28A 109.5 . . ?
C227 C228 H28B 109.5 . . ?
H28A C228 H28B 109.5 . . ?
C227 C228 H28C 109.5 . . ?
H28A C228 H28C 109.5 . . ?
H28B C228 H28C 109.5 . . ?
C227 C229 H29X 109.5 . . ?
C227 C229 H29Y 109.5 . . ?
H29X C229 H29Y 109.5 . . ?
C227 C229 H29Z 109.5 . . ?
H29X C229 H29Z 109.5 . . ?
H29Y C229 H29Z 109.5 . . ?
B2 O43 C416 111.2(11) . . ?
B2 O44 C419 94.2(14) . . ?
C419 C416 C418 115(2) . . ?
C419 C416 O43 108.7(18) . . ?
C418 C416 O43 121.1(14) . . ?
C419 C416 C417 121.0(19) . . ?
C418 C416 C417 89.6(14) . . ?
O43 C416 C417 100.2(13) . . ?
C416 C417 H41X 109.5 . . ?
C416 C417 H41Y 109.5 . . ?
H41X C417 H41Y 109.5 . . ?
C416 C417 H41Z 109.5 . . ?
H41X C417 H41Z 109.5 . . ?
H41Y C417 H41Z 109.5 . . ?
C416 C418 H41D 109.5 . . ?
C416 C418 H41E 109.5 . . ?
H41D C418 H41E 109.5 . . ?
C416 C418 H41F 109.5 . . ?
H41D C418 H41F 109.5 . . ?
H41E C418 H41F 109.5 . . ?
C416 C419 C420 149(3) . . ?
C416 C419 O44 96(2) . . ?
C420 C419 O44 98(2) . . ?
C416 C419 C421 124(2) . . ?
C420 C419 C421 85.7(19) . . ?
O44 C419 C421 78.8(15) . . ?
C419 C420 H42X 109.5 . . ?
C419 C420 H42Y 109.5 . . ?
H42X C420 H42Y 109.5 . . ?
C419 C420 H42Z 109.5 . . ?
H42X C420 H42Z 109.5 . . ?
H42Y C420 H42Z 109.5 . . ?
C419 C421 H42D 109.5 . . ?
C419 C421 H42E 109.5 . . ?
H42D C421 H42E 109.5 . . ?
C419 C421 H42F 109.5 . . ?
H42D C421 H42F 109.5 . . ?
H42E C421 H42F 109.5 . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

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

data_UP097_a
_database_code_depnum_ccdc_archive 'CCDC 1529579'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H44 B2 N4 O6, 2(C6 H6)'
_chemical_formula_sum            'C48 H56 B2 N4 O6'
_chemical_formula_weight         806.58

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

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

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

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

_cell_length_a                   13.6001(9)
_cell_length_b                   15.4857(10)
_cell_length_c                   21.2461(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.861(2)
_cell_angle_gamma                90
_cell_volume                     4472.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38413
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.628
_diffrn_reflns_theta_max         26.083
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8845
_reflns_number_gt                6222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+4.5123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8845
_refine_ls_number_parameters     604
_refine_ls_number_restraints     216
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.027
_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
O5 O 0.45766(11) 0.77819(10) 0.43396(7) 0.0308(4) Uani 1 1 d . . . . .
O3 O 0.49771(12) 0.72434(10) 0.67223(7) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.38573(14) 0.58265(13) 0.41850(9) 0.0314(4) Uani 1 1 d . . . . .
B1 B 0.4252(2) 0.73868(18) 0.37521(12) 0.0306(6) Uani 1 1 d . . . . .
C1 C 0.43778(16) 0.63269(16) 0.37949(10) 0.0295(5) Uani 1 1 d . . . . .
O1 O 0.31990(12) 0.75999(11) 0.36437(8) 0.0387(4) Uani 1 1 d . . . . .
O6 O 0.46236(12) 0.74543(11) 0.55773(7) 0.0336(4) Uani 1 1 d . . . . .
O4 O 0.34428(13) 0.77561(12) 0.63277(8) 0.0420(4) Uani 1 1 d . . . . .
N2 N 0.49289(15) 0.57771(13) 0.34591(9) 0.0341(5) Uani 1 1 d . . . . .
B2 B 0.4514(2) 0.77777(18) 0.62068(13) 0.0322(6) Uani 1 1 d . . . . .
O2 O 0.47495(12) 0.77333(11) 0.31877(7) 0.0339(4) Uani 1 1 d . . . . .
C2 C 0.40784(19) 0.49710(16) 0.40885(13) 0.0392(6) Uani 1 1 d . . . . .
H2 H 0.3810 0.4491 0.4302 0.047 Uiso 1 1 calc R U . . .
C6 C 0.20910(19) 0.5973(2) 0.43517(13) 0.0456(7) Uani 1 1 d . . . . .
H6A H 0.2023 0.6253 0.3939 0.068 Uiso 1 1 calc R U . . .
H6B H 0.1602 0.6211 0.4633 0.068 Uiso 1 1 calc R U . . .
H6C H 0.1986 0.5350 0.4304 0.068 Uiso 1 1 calc R U . . .
C7 C 0.56338(19) 0.60152(19) 0.29706(12) 0.0420(6) Uani 1 1 d . . . . .
H7 H 0.5765 0.6649 0.3006 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5176(2) 0.5841(2) 0.23213(14) 0.0589(8) Uani 1 1 d . . . . .
H8A H 0.5643 0.5999 0.1999 0.088 Uiso 1 1 calc R U . . .
H8B H 0.4575 0.6184 0.2263 0.088 Uiso 1 1 calc R U . . .
H8C H 0.5014 0.5226 0.2283 0.088 Uiso 1 1 calc R U . . .
C9 C 0.6603(2) 0.5543(2) 0.30836(15) 0.0532(8) Uani 1 1 d . . . . .
H9A H 0.6504 0.4923 0.3011 0.080 Uiso 1 1 calc R U . . .
H9B H 0.6840 0.5637 0.3519 0.080 Uiso 1 1 calc R U . . .
H9C H 0.7090 0.5762 0.2793 0.080 Uiso 1 1 calc R U . . .
C10 C 0.49045(19) 0.87937(15) 0.62706(11) 0.0332(5) Uani 1 1 d . . . . .
C11 C 0.5647(2) 1.00283(17) 0.65566(13) 0.0484(7) Uani 1 1 d . . . . .
H11 H 0.6110 1.0420 0.6741 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4830(2) 1.02351(17) 0.62249(14) 0.0504(7) Uani 1 1 d . . . . .
H12 H 0.4602 1.0802 0.6132 0.060 Uiso 1 1 calc R U . . .
C13 C 0.6556(2) 0.86776(18) 0.68776(12) 0.0411(6) Uani 1 1 d . . . . .
H13 H 0.6416 0.8044 0.6866 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6705(3) 0.8944(2) 0.75598(14) 0.0575(8) Uani 1 1 d . . . . .
H14A H 0.6885 0.9557 0.7581 0.086 Uiso 1 1 calc R U . . .
H14B H 0.7233 0.8597 0.7757 0.086 Uiso 1 1 calc R U . . .
H14C H 0.6095 0.8851 0.7783 0.086 Uiso 1 1 calc R U . . .
C15 C 0.7463(2) 0.8844(2) 0.64998(15) 0.0516(7) Uani 1 1 d . . . . .
H15A H 0.7312 0.8727 0.6054 0.077 Uiso 1 1 calc R U . . .
H15B H 0.7997 0.8464 0.6650 0.077 Uiso 1 1 calc R U . . .
H15C H 0.7666 0.9447 0.6552 0.077 Uiso 1 1 calc R U . . .
C16 C 0.3444(2) 0.94235(18) 0.56667(13) 0.0450(7) Uani 1 1 d . . . . .
H16 H 0.3330 0.8807 0.5544 0.054 Uiso 1 1 calc R U . . .
C17 C 0.3511(3) 0.9958(3) 0.50638(18) 0.0770(11) Uani 1 1 d . . . . .
H17A H 0.4088 0.9776 0.4833 0.116 Uiso 1 1 calc R U . . .
H17B H 0.3572 1.0571 0.5173 0.116 Uiso 1 1 calc R U . . .
H17C H 0.2915 0.9870 0.4800 0.116 Uiso 1 1 calc R U . . .
C18 C 0.2605(3) 0.9707(3) 0.6072(2) 0.0783(12) Uani 1 1 d . . . . .
H18A H 0.2703 1.0310 0.6199 0.117 Uiso 1 1 calc R U . . .
H18B H 0.2588 0.9341 0.6448 0.117 Uiso 1 1 calc R U . . .
H18C H 0.1981 0.9653 0.5831 0.117 Uiso 1 1 calc R U . . .
C19 C 0.3113(2) 0.79700(16) 0.30648(12) 0.0393(6) Uani 1 1 d . . . . .
C20 C 0.2273(2) 0.82671(19) 0.27630(15) 0.0531(8) Uani 1 1 d . . . . .
H20 H 0.1651 0.8225 0.2952 0.064 Uiso 1 1 calc R U . . .
C21 C 0.2364(3) 0.8634(2) 0.21681(17) 0.0658(10) Uani 1 1 d . . . . .
H21 H 0.1795 0.8846 0.1949 0.079 Uiso 1 1 calc R U . . .
C22 C 0.3258(3) 0.8694(2) 0.18944(14) 0.0646(10) Uani 1 1 d . . . . .
H22 H 0.3297 0.8948 0.1489 0.077 Uiso 1 1 calc R U . . .
C23 C 0.4118(3) 0.83879(17) 0.22014(12) 0.0493(7) Uani 1 1 d . . . . .
H23 H 0.4739 0.8421 0.2011 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4020(2) 0.80372(15) 0.27907(11) 0.0349(6) Uani 1 1 d . . . . .
C25 C 0.42482(19) 0.70383(15) 0.71187(11) 0.0340(6) Uani 1 1 d . . . . .
C26 C 0.4331(2) 0.66083(19) 0.76805(12) 0.0483(7) Uani 1 1 d . . . . .
H26 H 0.4951 0.6414 0.7843 0.058 Uiso 1 1 calc R U . . .
C27 C 0.3469(3) 0.6465(2) 0.80071(14) 0.0619(9) Uani 1 1 d . . . . .
H27 H 0.3504 0.6169 0.8399 0.074 Uiso 1 1 calc R U . . .
C28 C 0.2575(3) 0.6745(2) 0.77709(14) 0.0589(9) Uani 1 1 d . . . . .
H28 H 0.2000 0.6634 0.8000 0.071 Uiso 1 1 calc R U . . .
C29 C 0.2490(2) 0.71930(18) 0.71962(14) 0.0478(7) Uani 1 1 d . . . . .
H29 H 0.1871 0.7389 0.7032 0.057 Uiso 1 1 calc R U . . .
C30 C 0.3345(2) 0.73342(16) 0.68820(12) 0.0377(6) Uani 1 1 d . . . . .
C37 C 0.9215(3) 0.5968(3) 0.3122(3) 0.0906(15) Uani 1 1 d . . . . .
H37 H 0.9201 0.6267 0.2731 0.109 Uiso 1 1 calc R U . . .
C36 C 0.54882(17) 0.74273(14) 0.52772(10) 0.0273(5) Uani 1 1 d . . . . .
C35 C 0.63845(18) 0.72260(16) 0.55746(11) 0.0341(6) Uani 1 1 d . . . . .
H35 H 0.6412 0.7127 0.6016 0.041 Uiso 1 1 calc R U . . .
C34 C 0.72381(19) 0.71670(18) 0.52398(12) 0.0396(6) Uani 1 1 d . . . . .
H34 H 0.7845 0.7030 0.5451 0.048 Uiso 1 1 calc R U . . .
C33 C 0.72052(19) 0.73072(19) 0.46004(12) 0.0418(6) Uani 1 1 d . . . . .
H33 H 0.7789 0.7269 0.4368 0.050 Uiso 1 1 calc R U . . .
C32 C 0.63160(19) 0.75046(17) 0.42958(11) 0.0366(6) Uani 1 1 d . . . . .
H32 H 0.6297 0.7598 0.3854 0.044 Uiso 1 1 calc R U . . .
C31 C 0.54544(17) 0.75679(14) 0.46241(10) 0.0276(5) Uani 1 1 d . . . . .
C38 C 0.9417(3) 0.6407(3) 0.3671(3) 0.0928(15) Uani 1 1 d . . . . .
H38 H 0.9552 0.7008 0.3660 0.111 Uiso 1 1 calc R U . . .
C39 C 0.9426(3) 0.5981(3) 0.4233(2) 0.0834(13) Uani 1 1 d . . . . .
H39 H 0.9560 0.6290 0.4612 0.100 Uiso 1 1 calc R U . . .
C40 C 0.9246(3) 0.5123(3) 0.4254(2) 0.0802(12) Uani 1 1 d . . . . .
H40 H 0.9256 0.4830 0.4647 0.096 Uiso 1 1 calc R U . . .
C41 C 0.9048(3) 0.4677(3) 0.3703(2) 0.0749(11) Uani 1 1 d . . . . .
H41 H 0.8921 0.4074 0.3718 0.090 Uiso 1 1 calc R U . . .
C42 C 0.9032(3) 0.5092(3) 0.3136(2) 0.0786(11) Uani 1 1 d . . . . .
H42 H 0.8897 0.4782 0.2757 0.094 Uiso 1 1 calc R U . . .
C5 C 0.3292(2) 0.57073(19) 0.52691(12) 0.0454(7) Uani 1 1 d . . . . .
H5A H 0.3150 0.5088 0.5232 0.068 Uiso 1 1 calc R U . . .
H5B H 0.2855 0.5967 0.5575 0.068 Uiso 1 1 calc R U . . .
H5C H 0.3978 0.5789 0.5412 0.068 Uiso 1 1 calc R U . . .
C4 C 0.31231(17) 0.61369(17) 0.46317(11) 0.0336(5) Uani 1 1 d . . . . .
H4 H 0.3211 0.6774 0.4686 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4741(2) 0.49403(17) 0.36376(13) 0.0416(6) Uani 1 1 d . . . . .
H3 H 0.5029 0.4434 0.3471 0.050 Uiso 1 1 calc R U . . .
N3_2 N 0.56925(17) 0.91386(13) 0.65817(10) 0.0384(5) Uani 1 1 d . . . . .
N4_2 N 0.43729(17) 0.94707(13) 0.60404(10) 0.0391(5) Uani 1 1 d . . . . .
C1_5 C 0.6525(14) 0.6780(14) -0.0205(8) 0.0697(13) Uani 0.477(8) 1 d . U P A 1
H1_5 H 0.7175 0.6921 -0.0320 0.084 Uiso 0.477(8) 1 calc R U P A 1
C2_5 C 0.5969(7) 0.6205(7) -0.0578(5) 0.0736(13) Uani 0.477(8) 1 d . U P A 1
H2_5 H 0.6223 0.5962 -0.0950 0.088 Uiso 0.477(8) 1 calc R U P A 1
C3_5 C 0.5010(8) 0.5999(8) -0.0380(5) 0.0783(14) Uani 0.477(8) 1 d . U P A 1
H3_5 H 0.4612 0.5598 -0.0610 0.094 Uiso 0.477(8) 1 calc R U P A 1
C4_5 C 0.4650(8) 0.6413(8) 0.0180(7) 0.0771(13) Uani 0.477(8) 1 d . U P A 1
H4_5 H 0.3994 0.6306 0.0300 0.092 Uiso 0.477(8) 1 calc R U P A 1
C5_5 C 0.5229(9) 0.6950(7) 0.0539(5) 0.0735(13) Uani 0.477(8) 1 d . U P A 1
H5_5 H 0.5008 0.7185 0.0923 0.088 Uiso 0.477(8) 1 calc R U P A 1
C6_5 C 0.6151(8) 0.7140(10) 0.0321(8) 0.0723(13) Uani 0.477(8) 1 d . U P A 1
H6_5 H 0.6546 0.7544 0.0551 0.087 Uiso 0.477(8) 1 calc R U P A 1
C11_5 C 0.6385(12) 0.6752(13) -0.0303(7) 0.0701(13) Uani 0.523(8) 1 d . U P A 2
H11_5 H 0.6931 0.6813 -0.0567 0.084 Uiso 0.523(8) 1 calc R U P A 2
C12_5 C 0.5568(7) 0.6317(7) -0.0519(5) 0.0755(12) Uani 0.523(8) 1 d . U P A 2
H12_5 H 0.5566 0.6031 -0.0915 0.091 Uiso 0.523(8) 1 calc R U P A 2
C13_5 C 0.4737(7) 0.6299(7) -0.0153(6) 0.0770(13) Uani 0.523(8) 1 d . U P A 2
H13_5 H 0.4155 0.6012 -0.0296 0.092 Uiso 0.523(8) 1 calc R U P A 2
C14_5 C 0.4783(8) 0.6704(8) 0.0418(5) 0.0745(13) Uani 0.523(8) 1 d . U P A 2
H14_5 H 0.4208 0.6710 0.0660 0.089 Uiso 0.523(8) 1 calc R U P A 2
C15_5 C 0.5597(7) 0.7095(6) 0.0658(5) 0.0710(13) Uani 0.523(8) 1 d . U P A 2
H15_5 H 0.5592 0.7355 0.1062 0.085 Uiso 0.523(8) 1 calc R U P A 2
C16_5 C 0.6429(7) 0.7115(9) 0.0317(7) 0.0699(13) Uani 0.523(8) 1 d . U P A 2
H16_5 H 0.7019 0.7363 0.0485 0.084 Uiso 0.523(8) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C31 1.361(3) . ?
O5 B1 1.446(3) . ?
O3 C25 1.359(3) . ?
O3 B2 1.495(3) . ?
N1 C1 1.352(3) . ?
N1 C2 1.375(3) . ?
N1 C4 1.480(3) . ?
B1 O1 1.481(3) . ?
B1 O2 1.495(3) . ?
B1 C1 1.652(4) . ?
C1 N2 1.353(3) . ?
O1 C19 1.358(3) . ?
O6 C36 1.356(3) . ?
O6 B2 1.440(3) . ?
O4 C30 1.357(3) . ?
O4 B2 1.488(3) . ?
N2 C3 1.376(3) . ?
N2 C7 1.482(3) . ?
B2 C10 1.665(4) . ?
O2 C24 1.365(3) . ?
C2 C3 1.337(4) . ?
C2 H2 0.9500 . ?
C6 C4 1.528(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.520(4) . ?
C7 C9 1.520(4) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N3_2 1.351(3) . ?
C10 N4_2 1.356(3) . ?
C11 C12 1.336(4) . ?
C11 N3_2 1.380(3) . ?
C11 H11 0.9500 . ?
C12 N4_2 1.387(3) . ?
C12 H12 0.9500 . ?
C13 N3_2 1.495(3) . ?
C13 C14 1.514(4) . ?
C13 C15 1.515(4) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N4_2 1.472(4) . ?
C16 C18 1.517(4) . ?
C16 C17 1.530(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 C20 1.371(4) . ?
C19 C24 1.386(4) . ?
C20 C21 1.395(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.367(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.403(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9500 . ?
C25 C26 1.368(4) . ?
C25 C30 1.390(4) . ?
C26 C27 1.399(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.371(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.406(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9500 . ?
C37 C38 1.370(7) . ?
C37 C42 1.381(6) . ?
C37 H37 0.9500 . ?
C36 C35 1.390(3) . ?
C36 C31 1.404(3) . ?
C35 C34 1.384(4) . ?
C35 H35 0.9500 . ?
C34 C33 1.375(4) . ?
C34 H34 0.9500 . ?
C33 C32 1.387(4) . ?
C33 H33 0.9500 . ?
C32 C31 1.387(3) . ?
C32 H32 0.9500 . ?
C38 C39 1.363(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.352(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.379(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.364(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C5 C4 1.520(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 H4 1.0000 . ?
C3 H3 0.9500 . ?
C1_5 C6_5 1.36(3) . ?
C1_5 C2_5 1.398(19) . ?
C1_5 H1_5 0.9500 . ?
C2_5 C3_5 1.419(13) . ?
C2_5 H2_5 0.9500 . ?
C3_5 C4_5 1.451(15) . ?
C3_5 H3_5 0.9500 . ?
C4_5 C5_5 1.362(14) . ?
C4_5 H4_5 0.9500 . ?
C5_5 C6_5 1.382(15) . ?
C5_5 H5_5 0.9500 . ?
C6_5 H6_5 0.9500 . ?
C11_5 C12_5 1.366(16) . ?
C11_5 C16_5 1.43(2) . ?
C11_5 H11_5 0.9500 . ?
C12_5 C13_5 1.392(13) . ?
C12_5 H12_5 0.9500 . ?
C13_5 C14_5 1.365(13) . ?
C13_5 H13_5 0.9500 . ?
C14_5 C15_5 1.348(12) . ?
C14_5 H14_5 0.9500 . ?
C15_5 C16_5 1.363(14) . ?
C15_5 H15_5 0.9500 . ?
C16_5 H16_5 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
C31 O5 B1 121.25(18) . . ?
C25 O3 B2 106.56(19) . . ?
C1 N1 C2 109.8(2) . . ?
C1 N1 C4 125.8(2) . . ?
C2 N1 C4 124.3(2) . . ?
O5 B1 O1 107.8(2) . . ?
O5 B1 O2 114.0(2) . . ?
O1 B1 O2 104.82(18) . . ?
O5 B1 C1 110.16(19) . . ?
O1 B1 C1 109.1(2) . . ?
O2 B1 C1 110.6(2) . . ?
N1 C1 N2 105.8(2) . . ?
N1 C1 B1 123.2(2) . . ?
N2 C1 B1 130.9(2) . . ?
C19 O1 B1 106.83(19) . . ?
C36 O6 B2 124.37(19) . . ?
C30 O4 B2 106.6(2) . . ?
C1 N2 C3 109.6(2) . . ?
C1 N2 C7 126.5(2) . . ?
C3 N2 C7 123.9(2) . . ?
O6 B2 O4 106.5(2) . . ?
O6 B2 O3 115.7(2) . . ?
O4 B2 O3 104.62(19) . . ?
O6 B2 C10 111.2(2) . . ?
O4 B2 C10 108.6(2) . . ?
O3 B2 C10 109.7(2) . . ?
C24 O2 B1 106.32(19) . . ?
C3 C2 N1 107.3(2) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 109.6(2) . . ?
N2 C7 C9 110.3(2) . . ?
C8 C7 C9 112.7(2) . . ?
N2 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C9 C7 H7 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3_2 C10 N4_2 106.0(2) . . ?
N3_2 C10 B2 131.2(2) . . ?
N4_2 C10 B2 122.5(2) . . ?
C12 C11 N3_2 107.2(3) . . ?
C12 C11 H11 126.4 . . ?
N3_2 C11 H11 126.4 . . ?
C11 C12 N4_2 107.6(2) . . ?
C11 C12 H12 126.2 . . ?
N4_2 C12 H12 126.2 . . ?
N3_2 C13 C14 110.6(2) . . ?
N3_2 C13 C15 109.8(2) . . ?
C14 C13 C15 112.0(2) . . ?
N3_2 C13 H13 108.1 . . ?
C14 C13 H13 108.1 . . ?
C15 C13 H13 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4_2 C16 C18 109.1(2) . . ?
N4_2 C16 C17 110.6(2) . . ?
C18 C16 C17 112.6(3) . . ?
N4_2 C16 H16 108.1 . . ?
C18 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
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 . . ?
O1 C19 C20 127.7(3) . . ?
O1 C19 C24 111.1(2) . . ?
C20 C19 C24 121.2(3) . . ?
C19 C20 C21 117.6(3) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 117.0(3) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
O2 C24 C23 127.6(3) . . ?
O2 C24 C19 110.7(2) . . ?
C23 C24 C19 121.7(3) . . ?
O3 C25 C26 127.8(3) . . ?
O3 C25 C30 110.6(2) . . ?
C26 C25 C30 121.5(2) . . ?
C25 C26 C27 117.6(3) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C28 C27 C26 121.1(3) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 121.4(3) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 116.9(3) . . ?
C30 C29 H29 121.5 . . ?
C28 C29 H29 121.5 . . ?
O4 C30 C29 127.3(3) . . ?
O4 C30 C25 111.2(2) . . ?
C29 C30 C25 121.5(3) . . ?
C38 C37 C42 119.9(4) . . ?
C38 C37 H37 120.0 . . ?
C42 C37 H37 120.0 . . ?
O6 C36 C35 123.6(2) . . ?
O6 C36 C31 117.3(2) . . ?
C35 C36 C31 119.0(2) . . ?
C34 C35 C36 121.3(2) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C33 C34 C35 119.8(2) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C33 C32 119.7(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C31 C32 C33 121.3(2) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
O5 C31 C32 122.5(2) . . ?
O5 C31 C36 118.5(2) . . ?
C32 C31 C36 119.0(2) . . ?
C39 C38 C37 120.1(4) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C40 C39 C38 120.6(5) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C39 C40 C41 119.6(4) . . ?
C39 C40 H40 120.2 . . ?
C41 C40 H40 120.2 . . ?
C42 C41 C40 120.7(4) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C37 119.0(5) . . ?
C41 C42 H42 120.5 . . ?
C37 C42 H42 120.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 C5 110.1(2) . . ?
N1 C4 C6 109.1(2) . . ?
C5 C4 C6 112.6(2) . . ?
N1 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
C6 C4 H4 108.3 . . ?
C2 C3 N2 107.4(2) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
C10 N3_2 C11 110.0(2) . . ?
C10 N3_2 C13 128.1(2) . . ?
C11 N3_2 C13 121.8(2) . . ?
C10 N4_2 C12 109.2(2) . . ?
C10 N4_2 C16 126.5(2) . . ?
C12 N4_2 C16 124.3(2) . . ?
C6_5 C1_5 C2_5 121.1(17) . . ?
C6_5 C1_5 H1_5 119.4 . . ?
C2_5 C1_5 H1_5 119.4 . . ?
C1_5 C2_5 C3_5 117.4(13) . . ?
C1_5 C2_5 H2_5 121.3 . . ?
C3_5 C2_5 H2_5 121.3 . . ?
C2_5 C3_5 C4_5 118.8(10) . . ?
C2_5 C3_5 H3_5 120.6 . . ?
C4_5 C3_5 H3_5 120.6 . . ?
C5_5 C4_5 C3_5 121.6(10) . . ?
C5_5 C4_5 H4_5 119.2 . . ?
C3_5 C4_5 H4_5 119.2 . . ?
C4_5 C5_5 C6_5 117.2(11) . . ?
C4_5 C5_5 H5_5 121.4 . . ?
C6_5 C5_5 H5_5 121.4 . . ?
C1_5 C6_5 C5_5 123.7(16) . . ?
C1_5 C6_5 H6_5 118.2 . . ?
C5_5 C6_5 H6_5 118.2 . . ?
C12_5 C11_5 C16_5 120.8(15) . . ?
C12_5 C11_5 H11_5 119.6 . . ?
C16_5 C11_5 H11_5 119.6 . . ?
C11_5 C12_5 C13_5 119.2(12) . . ?
C11_5 C12_5 H12_5 120.4 . . ?
C13_5 C12_5 H12_5 120.4 . . ?
C14_5 C13_5 C12_5 118.2(9) . . ?
C14_5 C13_5 H13_5 120.9 . . ?
C12_5 C13_5 H13_5 120.9 . . ?
C15_5 C14_5 C13_5 123.8(9) . . ?
C15_5 C14_5 H14_5 118.1 . . ?
C13_5 C14_5 H14_5 118.1 . . ?
C14_5 C15_5 C16_5 119.7(10) . . ?
C14_5 C15_5 H15_5 120.2 . . ?
C16_5 C15_5 H15_5 120.2 . . ?
C15_5 C16_5 C11_5 118.0(12) . . ?
C15_5 C16_5 H16_5 121.0 . . ?
C11_5 C16_5 H16_5 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 O5 B1 O1 167.43(18) . . . . ?
C31 O5 B1 O2 -76.6(3) . . . . ?
C31 O5 B1 C1 48.4(3) . . . . ?
C2 N1 C1 N2 -0.5(2) . . . . ?
C4 N1 C1 N2 -177.89(19) . . . . ?
C2 N1 C1 B1 176.4(2) . . . . ?
C4 N1 C1 B1 -1.0(3) . . . . ?
O5 B1 C1 N1 65.6(3) . . . . ?
O1 B1 C1 N1 -52.6(3) . . . . ?
O2 B1 C1 N1 -167.44(19) . . . . ?
O5 B1 C1 N2 -118.4(3) . . . . ?
O1 B1 C1 N2 123.4(2) . . . . ?
O2 B1 C1 N2 8.6(3) . . . . ?
O5 B1 O1 C19 125.5(2) . . . . ?
O2 B1 O1 C19 3.7(2) . . . . ?
C1 B1 O1 C19 -114.8(2) . . . . ?
N1 C1 N2 C3 0.6(2) . . . . ?
B1 C1 N2 C3 -176.0(2) . . . . ?
N1 C1 N2 C7 -179.4(2) . . . . ?
B1 C1 N2 C7 4.0(4) . . . . ?
C36 O6 B2 O4 175.40(19) . . . . ?
C36 O6 B2 O3 -68.8(3) . . . . ?
C36 O6 B2 C10 57.3(3) . . . . ?
C30 O4 B2 O6 128.6(2) . . . . ?
C30 O4 B2 O3 5.6(2) . . . . ?
C30 O4 B2 C10 -111.5(2) . . . . ?
C25 O3 B2 O6 -123.0(2) . . . . ?
C25 O3 B2 O4 -6.2(2) . . . . ?
C25 O3 B2 C10 110.2(2) . . . . ?
O5 B1 O2 C24 -122.3(2) . . . . ?
O1 B1 O2 C24 -4.6(2) . . . . ?
C1 B1 O2 C24 112.9(2) . . . . ?
C1 N1 C2 C3 0.2(3) . . . . ?
C4 N1 C2 C3 177.6(2) . . . . ?
C1 N2 C7 C8 -103.2(3) . . . . ?
C3 N2 C7 C8 76.8(3) . . . . ?
C1 N2 C7 C9 132.1(3) . . . . ?
C3 N2 C7 C9 -47.9(3) . . . . ?
O6 B2 C10 N3_2 -110.8(3) . . . . ?
O4 B2 C10 N3_2 132.3(3) . . . . ?
O3 B2 C10 N3_2 18.5(4) . . . . ?
O6 B2 C10 N4_2 76.0(3) . . . . ?
O4 B2 C10 N4_2 -40.8(3) . . . . ?
O3 B2 C10 N4_2 -154.7(2) . . . . ?
N3_2 C11 C12 N4_2 -0.5(3) . . . . ?
B1 O1 C19 C20 179.6(3) . . . . ?
B1 O1 C19 C24 -1.5(3) . . . . ?
O1 C19 C20 C21 179.3(3) . . . . ?
C24 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
B1 O2 C24 C23 -177.5(2) . . . . ?
B1 O2 C24 C19 3.9(3) . . . . ?
C22 C23 C24 O2 -177.0(2) . . . . ?
C22 C23 C24 C19 1.4(4) . . . . ?
O1 C19 C24 O2 -1.6(3) . . . . ?
C20 C19 C24 O2 177.4(2) . . . . ?
O1 C19 C24 C23 179.7(2) . . . . ?
C20 C19 C24 C23 -1.3(4) . . . . ?
B2 O3 C25 C26 -175.1(3) . . . . ?
B2 O3 C25 C30 4.6(2) . . . . ?
O3 C25 C26 C27 -179.6(2) . . . . ?
C30 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C28 0.1(5) . . . . ?
C26 C27 C28 C29 -0.7(5) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
B2 O4 C30 C29 176.9(3) . . . . ?
B2 O4 C30 C25 -3.1(3) . . . . ?
C28 C29 C30 O4 -179.3(3) . . . . ?
C28 C29 C30 C25 0.7(4) . . . . ?
O3 C25 C30 O4 -1.0(3) . . . . ?
C26 C25 C30 O4 178.7(2) . . . . ?
O3 C25 C30 C29 179.0(2) . . . . ?
C26 C25 C30 C29 -1.3(4) . . . . ?
B2 O6 C36 C35 38.0(3) . . . . ?
B2 O6 C36 C31 -145.4(2) . . . . ?
O6 C36 C35 C34 176.9(2) . . . . ?
C31 C36 C35 C34 0.3(3) . . . . ?
C36 C35 C34 C33 -0.2(4) . . . . ?
C35 C34 C33 C32 -0.2(4) . . . . ?
C34 C33 C32 C31 0.3(4) . . . . ?
B1 O5 C31 C32 45.7(3) . . . . ?
B1 O5 C31 C36 -135.9(2) . . . . ?
C33 C32 C31 O5 178.3(2) . . . . ?
C33 C32 C31 C36 -0.1(4) . . . . ?
O6 C36 C31 O5 4.6(3) . . . . ?
C35 C36 C31 O5 -178.7(2) . . . . ?
O6 C36 C31 C32 -176.9(2) . . . . ?
C35 C36 C31 C32 -0.2(3) . . . . ?
C42 C37 C38 C39 -0.8(6) . . . . ?
C37 C38 C39 C40 0.7(6) . . . . ?
C38 C39 C40 C41 -0.3(6) . . . . ?
C39 C40 C41 C42 0.0(6) . . . . ?
C40 C41 C42 C37 -0.2(6) . . . . ?
C38 C37 C42 C41 0.6(6) . . . . ?
C1 N1 C4 C5 -134.1(2) . . . . ?
C2 N1 C4 C5 48.9(3) . . . . ?
C1 N1 C4 C6 101.9(3) . . . . ?
C2 N1 C4 C6 -75.2(3) . . . . ?
N1 C2 C3 N2 0.2(3) . . . . ?
C1 N2 C3 C2 -0.5(3) . . . . ?
C7 N2 C3 C2 179.5(2) . . . . ?
N4_2 C10 N3_2 C11 1.1(3) . . . . ?
B2 C10 N3_2 C11 -173.0(2) . . . . ?
N4_2 C10 N3_2 C13 -174.3(2) . . . . ?
B2 C10 N3_2 C13 11.6(4) . . . . ?
C12 C11 N3_2 C10 -0.4(3) . . . . ?
C12 C11 N3_2 C13 175.4(2) . . . . ?
C14 C13 N3_2 C10 -126.6(3) . . . . ?
C15 C13 N3_2 C10 109.4(3) . . . . ?
C14 C13 N3_2 C11 58.5(3) . . . . ?
C15 C13 N3_2 C11 -65.5(3) . . . . ?
N3_2 C10 N4_2 C12 -1.3(3) . . . . ?
B2 C10 N4_2 C12 173.3(2) . . . . ?
N3_2 C10 N4_2 C16 -179.9(2) . . . . ?
B2 C10 N4_2 C16 -5.2(4) . . . . ?
C11 C12 N4_2 C10 1.1(3) . . . . ?
C11 C12 N4_2 C16 179.8(2) . . . . ?
C18 C16 N4_2 C10 107.4(3) . . . . ?
C17 C16 N4_2 C10 -128.2(3) . . . . ?
C18 C16 N4_2 C12 -71.0(3) . . . . ?
C17 C16 N4_2 C12 53.4(4) . . . . ?
C6_5 C1_5 C2_5 C3_5 -1(2) . . . . ?
C1_5 C2_5 C3_5 C4_5 2.0(15) . . . . ?
C2_5 C3_5 C4_5 C5_5 -4.0(15) . . . . ?
C3_5 C4_5 C5_5 C6_5 4.9(15) . . . . ?
C2_5 C1_5 C6_5 C5_5 2(3) . . . . ?
C4_5 C5_5 C6_5 C1_5 -4(2) . . . . ?
C16_5 C11_5 C12_5 C13_5 6(2) . . . . ?
C11_5 C12_5 C13_5 C14_5 -1.4(15) . . . . ?
C12_5 C13_5 C14_5 C15_5 -2.5(14) . . . . ?
C13_5 C14_5 C15_5 C16_5 1.5(14) . . . . ?
C14_5 C15_5 C16_5 C11_5 3.0(17) . . . . ?
C12_5 C11_5 C16_5 C15_5 -7(2) . . . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6

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

data_HS117
_database_code_depnum_ccdc_archive 'CCDC 1529580'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C51 H58 B2 N2 O4'
_chemical_formula_sum            'C51 H58 B2 N2 O4'
_chemical_formula_weight         784.61

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   14.1863(9)
_cell_length_b                   16.4798(10)
_cell_length_c                   18.9462(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4429.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9605
_cell_measurement_theta_min      2.178
_cell_measurement_theta_max      25.9745

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6485
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'TWINABS 2012/1 (Bruker 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82306
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         26.066
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8756
_reflns_number_gt                8153
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+0.9293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8756
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C5 C 0.63276(11) 0.77824(11) 0.59529(9) 0.0147(3) Uani 1 1 d . . . . .
C4 C 0.66112(11) 0.71567(11) 0.55049(8) 0.0134(3) Uani 1 1 d . . . . .
O4 O 0.48212(8) 0.66677(7) 0.49570(6) 0.0141(2) Uani 1 1 d . . . . .
C3 C 0.82787(11) 0.73520(11) 0.40362(8) 0.0142(3) Uani 1 1 d . . . . .
H3A H 0.8879 0.7637 0.3938 0.017 Uiso 1 1 calc R U . . .
H3B H 0.8425 0.6776 0.4138 0.017 Uiso 1 1 calc R U . . .
O3 O 0.52265(8) 0.61524(7) 0.38331(6) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.78073(11) 0.77308(11) 0.46712(9) 0.0148(3) Uani 1 1 d . . . . .
H2A H 0.8199 0.7637 0.5096 0.018 Uiso 1 1 calc R U . . .
H2B H 0.7751 0.8324 0.4600 0.018 Uiso 1 1 calc R U . . .
N2 N 0.76648(9) 0.74019(9) 0.34144(7) 0.0129(3) Uani 1 1 d . . . . .
B2 B 0.52102(13) 0.69018(12) 0.42665(9) 0.0139(4) Uani 1 1 d . . . . .
O2 O 0.46193(8) 0.75493(7) 0.39767(6) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.62797(11) 0.72699(10) 0.42558(8) 0.0122(3) Uani 1 1 d . . . . .
N1 N 0.68516(9) 0.73738(8) 0.47809(7) 0.0121(3) Uani 1 1 d . . . . .
B1 B 0.66847(13) 0.74314(11) 0.34875(9) 0.0132(4) Uani 1 1 d . . . . .
O1 O 0.61475(8) 0.74816(8) 0.28930(6) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.60516(11) 0.75654(12) 0.66331(9) 0.0177(4) Uani 1 1 d . . . . .
H6 H 0.5838 0.7971 0.6952 0.021 Uiso 1 1 calc R U . . .
C20 C 0.91086(12) 0.77052(12) 0.18051(9) 0.0219(4) Uani 1 1 d . . . . .
H20 H 0.9355 0.8133 0.1524 0.026 Uiso 1 1 calc R U . . .
C21 C 0.85286(11) 0.78920(11) 0.23785(9) 0.0175(4) Uani 1 1 d . . . . .
C22 C 0.78306(13) 0.57345(11) 0.29645(9) 0.0189(4) Uani 1 1 d . . . . .
H22 H 0.7569 0.5957 0.3415 0.023 Uiso 1 1 calc R U . . .
C23 C 0.84487(13) 0.50062(12) 0.31580(10) 0.0239(4) Uani 1 1 d . . . . .
H23A H 0.8733 0.4781 0.2729 0.036 Uiso 1 1 calc R U . . .
H23B H 0.8061 0.4590 0.3387 0.036 Uiso 1 1 calc R U . . .
H23C H 0.8948 0.5181 0.3482 0.036 Uiso 1 1 calc R U . . .
C24 C 0.69910(13) 0.54677(12) 0.25101(11) 0.0254(4) Uani 1 1 d . . . . .
H24A H 0.6592 0.5938 0.2408 0.038 Uiso 1 1 calc R U . . .
H24B H 0.6623 0.5059 0.2766 0.038 Uiso 1 1 calc R U . . .
H24C H 0.7222 0.5235 0.2067 0.038 Uiso 1 1 calc R U . . .
C25 C 0.82302(13) 0.87616(11) 0.25364(9) 0.0205(4) Uani 1 1 d . . . . .
H25 H 0.7985 0.8776 0.3031 0.025 Uiso 1 1 calc R U . . .
C26 C 0.74187(14) 0.89969(13) 0.20447(12) 0.0324(5) Uani 1 1 d . . . . .
H01A H 0.7639 0.8989 0.1555 0.049 Uiso 1 1 calc R U . . .
H01B H 0.7197 0.9543 0.2164 0.049 Uiso 1 1 calc R U . . .
H01C H 0.6900 0.8609 0.2100 0.049 Uiso 1 1 calc R U . . .
C27 C 0.90274(13) 0.93811(12) 0.24851(10) 0.0254(4) Uani 1 1 d . . . . .
H27A H 0.9273 0.9390 0.2002 0.038 Uiso 1 1 calc R U . . .
H27B H 0.9534 0.9231 0.2812 0.038 Uiso 1 1 calc R U . . .
H27C H 0.8787 0.9920 0.2609 0.038 Uiso 1 1 calc R U . . .
C28 C 0.52110(11) 0.76602(10) 0.27665(9) 0.0144(3) Uani 1 1 d . . . . .
C29 C 0.50087(12) 0.78430(11) 0.20655(9) 0.0172(4) Uani 1 1 d . . . . .
H29 H 0.5496 0.7812 0.1723 0.021 Uiso 1 1 calc R U . . .
C30 C 0.41097(12) 0.80695(11) 0.18570(9) 0.0196(4) Uani 1 1 d . . . . .
H30 H 0.3982 0.8195 0.1377 0.024 Uiso 1 1 calc R U . . .
C31 C 0.33991(12) 0.81095(11) 0.23597(9) 0.0196(4) Uani 1 1 d . . . . .
H31 H 0.2780 0.8269 0.2227 0.024 Uiso 1 1 calc R U . . .
C32 C 0.35970(12) 0.79151(11) 0.30557(9) 0.0171(4) Uani 1 1 d . . . . .
H32 H 0.3104 0.7936 0.3394 0.021 Uiso 1 1 calc R U . . .
C33 C 0.44958(12) 0.76897(10) 0.32728(9) 0.0145(3) Uani 1 1 d . . . . .
C34 C 0.48194(12) 0.55619(11) 0.42378(9) 0.0162(3) Uani 1 1 d . . . . .
C35 C 0.46563(13) 0.47631(11) 0.40584(10) 0.0214(4) Uani 1 1 d . . . . .
H35 H 0.4817 0.4559 0.3605 0.026 Uiso 1 1 calc R U . . .
C36 C 0.42437(14) 0.42637(12) 0.45730(11) 0.0266(4) Uani 1 1 d . . . . .
H36 H 0.4121 0.3710 0.4467 0.032 Uiso 1 1 calc R U . . .
C37 C 0.40133(13) 0.45666(12) 0.52314(11) 0.0261(4) Uani 1 1 d . . . . .
H37 H 0.3739 0.4215 0.5572 0.031 Uiso 1 1 calc R U . . .
C38 C 0.41753(12) 0.53788(12) 0.54070(10) 0.0212(4) Uani 1 1 d . . . . .
H38 H 0.4011 0.5587 0.5858 0.025 Uiso 1 1 calc R U . . .
C39 C 0.45823(11) 0.58656(11) 0.49000(9) 0.0154(3) Uani 1 1 d . . . . .
C40 C 0.68689(17) 0.69947(14) 0.07756(12) 0.0377(5) Uani 1 1 d . . . . .
H40 H 0.7076 0.7026 0.1252 0.045 Uiso 1 1 calc R U . . .
C41 C 0.73953(16) 0.73390(14) 0.02480(13) 0.0392(5) Uani 1 1 d . . . . .
H41 H 0.7967 0.7610 0.0360 0.047 Uiso 1 1 calc R U . . .
C42 C 0.71019(18) 0.72949(16) -0.04424(13) 0.0431(6) Uani 1 1 d . . . . .
H42 H 0.7472 0.7533 -0.0805 0.052 Uiso 1 1 calc R U . . .
C43 C 0.62733(19) 0.69069(17) -0.06085(13) 0.0482(7) Uani 1 1 d . . . . .
H43 H 0.6069 0.6879 -0.1085 0.058 Uiso 1 1 calc R U . . .
C44 C 0.57417(19) 0.65599(17) -0.00817(15) 0.0513(7) Uani 1 1 d . . . . .
H44 H 0.5169 0.6290 -0.0195 0.062 Uiso 1 1 calc R U . . .
C45 C 0.60392(19) 0.66027(15) 0.06140(13) 0.0433(6) Uani 1 1 d . . . . .
H45 H 0.5672 0.6363 0.0978 0.052 Uiso 1 1 calc R U . . .
C46 C 0.44676(14) 0.54628(12) 0.21767(10) 0.0253(4) Uani 1 1 d . . . . .
H46 H 0.4815 0.5626 0.2582 0.030 Uiso 1 1 calc R U . . .
C47 C 0.36867(15) 0.58998(13) 0.19698(12) 0.0328(5) Uani 1 1 d . . . . .
H47 H 0.3493 0.6362 0.2232 0.039 Uiso 1 1 calc R U . . .
C48 C 0.31886(17) 0.56634(14) 0.13802(15) 0.0461(6) Uani 1 1 d . . . . .
H48 H 0.2650 0.5963 0.1237 0.055 Uiso 1 1 calc R U . . .
C49 C 0.34683(17) 0.49927(14) 0.09955(13) 0.0418(6) Uani 1 1 d . . . . .
H49 H 0.3122 0.4833 0.0589 0.050 Uiso 1 1 calc R U . . .
C50 C 0.42521(15) 0.45545(13) 0.12020(11) 0.0302(5) Uani 1 1 d . . . . .
H50 H 0.4449 0.4096 0.0937 0.036 Uiso 1 1 calc R U . . .
C51 C 0.47475(14) 0.47885(12) 0.17970(11) 0.0257(4) Uani 1 1 d . . . . .
H51 H 0.5281 0.4485 0.1945 0.031 Uiso 1 1 calc R U . . .
C19 C 0.93313(13) 0.69107(13) 0.16385(10) 0.0248(4) Uani 1 1 d . . . . .
H19 H 0.9746 0.6799 0.1257 0.030 Uiso 1 1 calc R U . . .
C18 C 0.89510(13) 0.62776(12) 0.20267(9) 0.0217(4) Uani 1 1 d . . . . .
H18 H 0.9102 0.5734 0.1904 0.026 Uiso 1 1 calc R U . . .
C17 C 0.83488(12) 0.64257(11) 0.25963(9) 0.0167(4) Uani 1 1 d . . . . .
C16 C 0.81750(11) 0.72410(11) 0.27715(8) 0.0146(3) Uani 1 1 d . . . . .
C15 C 0.67332(14) 0.48455(11) 0.53371(10) 0.0217(4) Uani 1 1 d . . . . .
H15A H 0.6045 0.4865 0.5298 0.033 Uiso 1 1 calc R U . . .
H15B H 0.6909 0.4640 0.5804 0.033 Uiso 1 1 calc R U . . .
H15C H 0.6987 0.4485 0.4973 0.033 Uiso 1 1 calc R U . . .
C14 C 0.82112(13) 0.56764(12) 0.53684(10) 0.0227(4) Uani 1 1 d . . . . .
H14A H 0.8507 0.5308 0.5028 0.034 Uiso 1 1 calc R U . . .
H14B H 0.8334 0.5483 0.5849 0.034 Uiso 1 1 calc R U . . .
H14C H 0.8473 0.6223 0.5312 0.034 Uiso 1 1 calc R U . . .
C13 C 0.71377(12) 0.57005(11) 0.52374(9) 0.0174(4) Uani 1 1 d . . . . .
H13 H 0.7031 0.5865 0.4736 0.021 Uiso 1 1 calc R U . . .
C12 C 0.54585(13) 0.91256(12) 0.58965(11) 0.0253(4) Uani 1 1 d . . . . .
H12A H 0.5519 0.9691 0.5741 0.038 Uiso 1 1 calc R U . . .
H12B H 0.5344 0.9111 0.6406 0.038 Uiso 1 1 calc R U . . .
H12C H 0.4930 0.8869 0.5649 0.038 Uiso 1 1 calc R U . . .
C11 C 0.72206(14) 0.90824(12) 0.60734(11) 0.0261(4) Uani 1 1 d . . . . .
H11A H 0.7792 0.8771 0.5968 0.039 Uiso 1 1 calc R U . . .
H11B H 0.7129 0.9106 0.6586 0.039 Uiso 1 1 calc R U . . .
H11C H 0.7286 0.9634 0.5886 0.039 Uiso 1 1 calc R U . . .
C10 C 0.63664(12) 0.86681(11) 0.57290(9) 0.0174(4) Uani 1 1 d . . . . .
H10 H 0.6460 0.8683 0.5206 0.021 Uiso 1 1 calc R U . . .
C9 C 0.66942(12) 0.63438(11) 0.57111(9) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.64111(12) 0.61628(11) 0.63959(9) 0.0176(4) Uani 1 1 d . . . . .
H8 H 0.6440 0.5618 0.6557 0.021 Uiso 1 1 calc R U . . .
C7 C 0.60869(12) 0.67630(12) 0.68478(9) 0.0190(4) Uani 1 1 d . . . . .
H7 H 0.5887 0.6622 0.7310 0.023 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
C5 C6 1.393(2) . ?
C5 C4 1.395(2) . ?
C5 C10 1.521(2) . ?
C4 C9 1.400(2) . ?
C4 N1 1.458(2) . ?
O4 C39 1.369(2) . ?
O4 B2 1.471(2) . ?
C3 N2 1.467(2) . ?
C3 C2 1.511(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O3 C34 1.367(2) . ?
O3 B2 1.483(2) . ?
C2 N1 1.493(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 B1 1.398(2) . ?
N2 C16 1.442(2) . ?
B2 O2 1.464(2) . ?
B2 C1 1.634(2) . ?
O2 C33 1.3649(19) . ?
C1 N1 1.295(2) . ?
C1 B1 1.587(2) . ?
B1 O1 1.362(2) . ?
O1 C28 1.3818(19) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C20 C19 1.383(3) . ?
C20 C21 1.397(2) . ?
C20 H20 0.9500 . ?
C21 C16 1.399(2) . ?
C21 C25 1.524(3) . ?
C22 C17 1.525(2) . ?
C22 C23 1.531(3) . ?
C22 C24 1.534(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C27 1.527(3) . ?
C25 C26 1.531(3) . ?
C25 H25 1.0000 . ?
C26 H01A 0.9800 . ?
C26 H01B 0.9800 . ?
C26 H01C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.392(2) . ?
C28 C33 1.397(2) . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.390(2) . ?
C32 H32 0.9500 . ?
C34 C35 1.379(3) . ?
C34 C39 1.392(2) . ?
C35 C36 1.404(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.398(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(2) . ?
C38 H38 0.9500 . ?
C40 C41 1.371(3) . ?
C40 C45 1.377(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.374(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.375(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.375(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.386(4) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.378(3) . ?
C46 C51 1.382(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.378(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.382(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.382(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.383(3) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C19 C18 1.386(3) . ?
C19 H19 0.9500 . ?
C18 C17 1.398(2) . ?
C18 H18 0.9500 . ?
C17 C16 1.406(2) . ?
C15 C13 1.533(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 C13 1.543(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 C9 1.525(2) . ?
C13 H13 1.0000 . ?
C12 C10 1.526(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 C10 1.536(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10 1.0000 . ?
C9 C8 1.390(2) . ?
C8 C7 1.387(3) . ?
C8 H8 0.9500 . ?
C7 H7 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
C6 C5 C4 117.01(16) . . ?
C6 C5 C10 120.96(15) . . ?
C4 C5 C10 121.95(15) . . ?
C5 C4 C9 124.16(15) . . ?
C5 C4 N1 117.30(15) . . ?
C9 C4 N1 118.52(14) . . ?
C39 O4 B2 106.01(13) . . ?
N2 C3 C2 110.69(13) . . ?
N2 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C34 O3 B2 106.00(13) . . ?
N1 C2 C3 110.48(13) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
B1 N2 C16 126.12(13) . . ?
B1 N2 C3 120.84(13) . . ?
C16 N2 C3 111.72(12) . . ?
O2 B2 O4 108.05(13) . . ?
O2 B2 O3 114.10(14) . . ?
O4 B2 O3 106.25(14) . . ?
O2 B2 C1 104.86(14) . . ?
O4 B2 C1 117.17(14) . . ?
O3 B2 C1 106.72(13) . . ?
C33 O2 B2 124.30(13) . . ?
N1 C1 B1 117.10(14) . . ?
N1 C1 B2 128.40(14) . . ?
B1 C1 B2 114.18(13) . . ?
C1 N1 C4 122.94(13) . . ?
C1 N1 C2 120.94(13) . . ?
C4 N1 C2 116.12(12) . . ?
O1 B1 N2 118.46(15) . . ?
O1 B1 C1 124.46(14) . . ?
N2 B1 C1 116.42(14) . . ?
B1 O1 C28 133.96(13) . . ?
C7 C6 C5 120.44(16) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C19 C20 C21 121.36(17) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 117.14(17) . . ?
C20 C21 C25 121.56(16) . . ?
C16 C21 C25 121.13(15) . . ?
C17 C22 C23 114.78(15) . . ?
C17 C22 C24 109.37(15) . . ?
C23 C22 C24 110.75(15) . . ?
C17 C22 H22 107.2 . . ?
C23 C22 H22 107.2 . . ?
C24 C22 H22 107.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 C27 114.24(15) . . ?
C21 C25 C26 109.12(16) . . ?
C27 C25 C26 110.42(15) . . ?
C21 C25 H25 107.6 . . ?
C27 C25 H25 107.6 . . ?
C26 C25 H25 107.6 . . ?
C25 C26 H01A 109.5 . . ?
C25 C26 H01B 109.5 . . ?
H01A C26 H01B 109.5 . . ?
C25 C26 H01C 109.5 . . ?
H01A C26 H01C 109.5 . . ?
H01B C26 H01C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 C28 C29 114.20(14) . . ?
O1 C28 C33 125.91(14) . . ?
C29 C28 C33 119.87(15) . . ?
C30 C29 C28 121.32(16) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 119.04(16) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C32 C31 C30 119.64(16) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 121.94(16) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
O2 C33 C32 116.88(14) . . ?
O2 C33 C28 124.88(15) . . ?
C32 C33 C28 118.17(15) . . ?
O3 C34 C35 127.75(16) . . ?
O3 C34 C39 110.59(15) . . ?
C35 C34 C39 121.65(16) . . ?
C34 C35 C36 117.28(18) . . ?
C34 C35 H35 121.4 . . ?
C36 C35 H35 121.4 . . ?
C37 C36 C35 120.90(18) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 121.43(18) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C39 C38 C37 117.39(17) . . ?
C39 C38 H38 121.3 . . ?
C37 C38 H38 121.3 . . ?
O4 C39 C38 127.64(16) . . ?
O4 C39 C34 111.00(14) . . ?
C38 C39 C34 121.34(17) . . ?
C41 C40 C45 119.8(2) . . ?
C41 C40 H40 120.1 . . ?
C45 C40 H40 120.1 . . ?
C40 C41 C42 120.5(2) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C43 120.1(2) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C42 C43 C44 119.7(2) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C43 C44 C45 120.1(3) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C40 C45 C44 119.7(2) . . ?
C40 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C47 C46 C51 120.20(19) . . ?
C47 C46 H46 119.9 . . ?
C51 C46 H46 119.9 . . ?
C48 C47 C46 119.7(2) . . ?
C48 C47 H47 120.2 . . ?
C46 C47 H47 120.2 . . ?
C47 C48 C49 120.4(2) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C48 C49 C50 120.0(2) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C49 C50 C51 119.6(2) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C46 C51 C50 120.16(19) . . ?
C46 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C20 C19 C18 120.18(16) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C18 C17 121.07(18) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C17 C16 117.15(16) . . ?
C18 C17 C22 121.16(16) . . ?
C16 C17 C22 121.43(15) . . ?
C21 C16 C17 122.98(15) . . ?
C21 C16 N2 119.27(15) . . ?
C17 C16 N2 117.60(15) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C13 C15 114.33(15) . . ?
C9 C13 C14 109.29(14) . . ?
C15 C13 C14 109.02(15) . . ?
C9 C13 H13 108.0 . . ?
C15 C13 H13 108.0 . . ?
C14 C13 H13 108.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C10 C12 112.69(15) . . ?
C5 C10 C11 109.68(15) . . ?
C12 C10 C11 110.97(15) . . ?
C5 C10 H10 107.8 . . ?
C12 C10 H10 107.8 . . ?
C11 C10 H10 107.8 . . ?
C8 C9 C4 116.18(16) . . ?
C8 C9 C13 121.28(16) . . ?
C4 C9 C13 122.38(15) . . ?
C7 C8 C9 121.26(17) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C6 C7 C8 120.79(16) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.030

_shelxl_version_number           2014/6

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

data_UP096_a
_database_code_depnum_ccdc_archive 'CCDC 1529581'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H37 B N4 O2'
_chemical_formula_sum            'C24 H37 B N4 O2'
_chemical_formula_weight         424.38

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

_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                   9.4793(8)
_cell_length_b                   9.8725(9)
_cell_length_c                   13.4421(11)
_cell_angle_alpha                79.620(2)
_cell_angle_beta                 78.062(2)
_cell_angle_gamma                87.549(2)
_cell_volume                     1210.60(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6198
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.04

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14459
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.573
_diffrn_reflns_theta_max         26.127
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4819
_reflns_number_gt                3802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0349P)²+0.4605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     383
_refine_ls_number_restraints     109
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
N2 N 0.56229(12) 0.63566(11) 0.18753(9) 0.0237(3) Uani 1 1 d . . . . .
C4 C 0.52968(15) 0.78083(14) 0.15180(11) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.5559 0.8347 0.2015 0.031 Uiso 1 1 calc R U . . .
C1 C 0.68868(19) 0.43123(18) 0.27956(14) 0.0220(4) Uani 0.909(2) 1 d . U P A 1
H1 H 0.6047 0.4021 0.3371 0.026 Uiso 0.909(2) 1 calc R U P A 1
C3 C 0.5303(2) 0.5399(2) 0.13047(15) 0.0257(5) Uani 0.909(2) 1 d . U P A 1
H2 H 0.4683 0.5691 0.0834 0.031 Uiso 0.909(2) 1 calc R U P A 1
N1 N 0.68072(14) 0.35315(13) 0.19735(10) 0.0244(3) Uani 0.909(2) 1 d . U P A 1
C2 C 0.58002(18) 0.41068(16) 0.13695(13) 0.0262(4) Uani 0.909(2) 1 d . U P A 1
H3 H 0.5451 0.3530 0.0980 0.031 Uiso 0.909(2) 1 calc R U P A 1
C7 C 0.6676(2) 0.2029(2) 0.23374(17) 0.0310(5) Uani 0.909(2) 1 d . U P A 1
H7 H 0.7460 0.1748 0.2730 0.037 Uiso 0.909(2) 1 calc R U P A 1
C8 C 0.6948(3) 0.1264(2) 0.14266(18) 0.0442(6) Uani 0.909(2) 1 d . U P A 1
H8A H 0.6079 0.1306 0.1134 0.066 Uiso 0.909(2) 1 calc R U P A 1
H8B H 0.7188 0.0300 0.1662 0.066 Uiso 0.909(2) 1 calc R U P A 1
H8C H 0.7751 0.1694 0.0898 0.066 Uiso 0.909(2) 1 calc R U P A 1
C9 C 0.5261(3) 0.1544(3) 0.3060(3) 0.0481(7) Uani 0.909(2) 1 d . U P A 1
H9A H 0.4468 0.1748 0.2690 0.072 Uiso 0.909(2) 1 calc R U P A 1
H9B H 0.5094 0.2022 0.3653 0.072 Uiso 0.909(2) 1 calc R U P A 1
H9C H 0.5312 0.0549 0.3303 0.072 Uiso 0.909(2) 1 calc R U P A 1
C11 C 0.721(2) 0.442(2) 0.2413(16) 0.0238(18) Uani 0.091(2) 1 d . U P A 2
H11 H 0.7760 0.4364 0.1702 0.029 Uiso 0.091(2) 1 calc R U P A 2
C13 C 0.497(3) 0.541(3) 0.161(2) 0.0273(19) Uani 0.091(2) 1 d . U P A 2
H12 H 0.4379 0.5693 0.1112 0.033 Uiso 0.091(2) 1 calc R U P A 2
N11 N 0.5962(15) 0.3519(12) 0.2645(10) 0.0230(16) Uani 0.091(2) 1 d . U P A 2
C12 C 0.5039(19) 0.4103(16) 0.1957(14) 0.0262(16) Uani 0.091(2) 1 d . U P A 2
H13 H 0.4450 0.3499 0.1746 0.031 Uiso 0.091(2) 1 calc R U P A 2
C17 C 0.627(3) 0.200(3) 0.267(2) 0.0305(18) Uani 0.091(2) 1 d . U P A 2
H17 H 0.6819 0.1617 0.3221 0.037 Uiso 0.091(2) 1 calc R U P A 2
C18 C 0.483(4) 0.175(4) 0.300(3) 0.050(4) Uani 0.091(2) 1 d . U P A 2
H18A H 0.4388 0.1756 0.2405 0.076 Uiso 0.091(2) 1 calc R U P A 2
H18B H 0.4387 0.2472 0.3382 0.076 Uiso 0.091(2) 1 calc R U P A 2
H18C H 0.4687 0.0853 0.3456 0.076 Uiso 0.091(2) 1 calc R U P A 2
C19 C 0.704(3) 0.172(3) 0.164(2) 0.045(3) Uani 0.091(2) 1 d . U P A 2
H19A H 0.7401 0.0773 0.1709 0.068 Uiso 0.091(2) 1 calc R U P A 2
H19B H 0.7846 0.2360 0.1368 0.068 Uiso 0.091(2) 1 calc R U P A 2
H19C H 0.6367 0.1853 0.1163 0.068 Uiso 0.091(2) 1 calc R U P A 2
C5 C 0.61992(16) 0.83672(15) 0.04566(11) 0.0305(3) Uani 1 1 d . . . . .
H5A H 0.5998 0.7839 -0.0049 0.046 Uiso 1 1 calc R U . . .
H5B H 0.7225 0.8284 0.0484 0.046 Uiso 1 1 calc R U . . .
H5C H 0.5955 0.9338 0.0252 0.046 Uiso 1 1 calc R U . . .
C6 C 0.36878(16) 0.80590(16) 0.15283(12) 0.0322(3) Uani 1 1 d . . . . .
H6A H 0.3489 0.9051 0.1426 0.048 Uiso 1 1 calc R U . . .
H6B H 0.3122 0.7616 0.2194 0.048 Uiso 1 1 calc R U . . .
H6C H 0.3423 0.7670 0.0971 0.048 Uiso 1 1 calc R U . . .
B1_1 B 0.67842(17) 0.60148(16) 0.24792(12) 0.0232(3) Uani 1 1 d . . . . .
O1_1 O 0.82194(10) 0.66889(10) 0.19421(7) 0.0267(2) Uani 1 1 d . . . . .
C1_1 C 0.85280(15) 0.75620(14) 0.25363(11) 0.0266(3) Uani 1 1 d . . . . .
O2_1 O 0.64534(10) 0.65636(10) 0.34886(7) 0.0259(2) Uani 1 1 d . . . . .
C3_1 C 0.75663(18) 0.83104(15) 0.41604(13) 0.0340(4) Uani 1 1 d . . . . .
H3_1 H 0.6854 0.8264 0.4777 0.041 Uiso 1 1 calc R U . . .
C4_1 C 0.87367(19) 0.92190(16) 0.39468(14) 0.0403(4) Uani 1 1 d . . . . .
H4_1 H 0.8821 0.9794 0.4427 0.048 Uiso 1 1 calc R U . . .
C5_1 C 0.97617(18) 0.92853(16) 0.30499(15) 0.0413(4) Uani 1 1 d . . . . .
H5_1 H 1.0545 0.9904 0.2923 0.050 Uiso 1 1 calc R U . . .
C6_1 C 0.96752(17) 0.84590(15) 0.23188(13) 0.0347(4) Uani 1 1 d . . . . .
H6_1 H 1.0379 0.8514 0.1697 0.042 Uiso 1 1 calc R U . . .
C2_1 C 0.74873(15) 0.74901(14) 0.34476(11) 0.0265(3) Uani 1 1 d . . . . .
C1_2 C 0.82116(15) 0.39084(13) 0.32101(11) 0.0236(3) Uani 1 1 d . . . . .
N1_2 N 0.82330(12) 0.35654(12) 0.42196(9) 0.0261(3) Uani 1 1 d . . . . .
C2_2 C 0.96349(16) 0.32526(16) 0.43307(12) 0.0321(3) Uani 1 1 d . . . . .
H2_2 H 0.9951 0.2977 0.4963 0.039 Uiso 1 1 calc R U . . .
N2_2 N 0.95786(12) 0.38292(12) 0.26871(9) 0.0261(3) Uani 1 1 d . . . . .
C3_2 C 1.04617(16) 0.34103(16) 0.33839(12) 0.0313(3) Uani 1 1 d . . . . .
H3_2 H 1.1474 0.3261 0.3220 0.038 Uiso 1 1 calc R U . . .
C4_2 C 0.69918(16) 0.34754(15) 0.51119(11) 0.0293(3) Uani 1 1 d . . . . .
H4_2 H 0.6110 0.3807 0.4840 0.035 Uiso 1 1 calc R U . . .
C5_2 C 0.67588(18) 0.19777(16) 0.56327(13) 0.0372(4) Uani 1 1 d . . . . .
H5A_2 H 0.6618 0.1425 0.5125 0.056 Uiso 1 1 calc R U . . .
H5B_2 H 0.5904 0.1909 0.6192 0.056 Uiso 1 1 calc R U . . .
H5C_2 H 0.7605 0.1635 0.5917 0.056 Uiso 1 1 calc R U . . .
C6_2 C 0.72380(18) 0.44099(16) 0.58380(12) 0.0357(4) Uani 1 1 d . . . . .
H6A_2 H 0.7391 0.5354 0.5458 0.053 Uiso 1 1 calc R U . . .
H6B_2 H 0.8089 0.4094 0.6124 0.053 Uiso 1 1 calc R U . . .
H6C_2 H 0.6392 0.4386 0.6401 0.053 Uiso 1 1 calc R U . . .
C7_2 C 1.0076(2) 0.4113(3) 0.1553(2) 0.0289(5) Uani 0.909(2) 1 d . U P A 1
H7_2 H 0.9245 0.4486 0.1233 0.035 Uiso 0.909(2) 1 calc R U P A 1
C8_2 C 1.0587(2) 0.2797(2) 0.11683(17) 0.0412(5) Uani 0.909(2) 1 d . U P A 1
H8A_2 H 1.0834 0.2978 0.0412 0.062 Uiso 0.909(2) 1 calc R U P A 1
H8B_2 H 0.9819 0.2109 0.1402 0.062 Uiso 0.909(2) 1 calc R U P A 1
H8C_2 H 1.1440 0.2449 0.1441 0.062 Uiso 0.909(2) 1 calc R U P A 1
C9_2 C 1.1263(3) 0.5202(4) 0.1264(2) 0.0379(6) Uani 0.909(2) 1 d . U P A 1
H9A_2 H 1.1546 0.5439 0.0510 0.057 Uiso 0.909(2) 1 calc R U P A 1
H9B_2 H 1.2101 0.4837 0.1550 0.057 Uiso 0.909(2) 1 calc R U P A 1
H9C_2 H 1.0902 0.6028 0.1546 0.057 Uiso 0.909(2) 1 calc R U P A 1
C18_2 C 1.134(3) 0.284(3) 0.118(2) 0.047(3) Uani 0.091(2) 1 d . U P A 2
H18A_2 H 1.1620 0.2944 0.0423 0.071 Uiso 0.091(2) 1 calc R U P A 2
H18B_2 H 1.0685 0.2061 0.1444 0.071 Uiso 0.091(2) 1 calc R U P A 2
H18C_2 H 1.2202 0.2686 0.1478 0.071 Uiso 0.091(2) 1 calc R U P A 2
C19_2 C 1.155(4) 0.526(5) 0.148(3) 0.040(4) Uani 0.091(2) 1 d . U P A 2
H19A_2 H 1.1107 0.6076 0.1736 0.060 Uiso 0.091(2) 1 calc R U P A 2
H19B_2 H 1.2088 0.5528 0.0768 0.060 Uiso 0.091(2) 1 calc R U P A 2
H19C_2 H 1.2211 0.4828 0.1918 0.060 Uiso 0.091(2) 1 calc R U P A 2
C17_2 C 1.048(3) 0.433(4) 0.150(3) 0.027(2) Uani 0.091(2) 1 d . U P A 2
H17_2 H 0.9825 0.4706 0.1019 0.033 Uiso 0.091(2) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C13 1.29(3) . ?
N2 C3 1.399(3) . ?
N2 C4 1.4683(17) . ?
N2 B1_1 1.4912(19) . ?
C4 C5 1.524(2) . ?
C4 C6 1.532(2) . ?
C4 H4 1.0000 . ?
C1 N1 1.472(2) . ?
C1 C1_2 1.488(2) . ?
C1 B1_1 1.662(2) . ?
C1 H1 1.0000 . ?
C3 C2 1.335(3) . ?
C3 H2 0.9500 . ?
N1 C2 1.4145(19) . ?
N1 C7 1.477(2) . ?
C2 H3 0.9500 . ?
C7 C9 1.523(4) . ?
C7 C8 1.524(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 N11 1.45(2) . ?
C11 C1_2 1.58(2) . ?
C11 B1_1 1.62(2) . ?
C11 H11 1.0000 . ?
C13 C12 1.30(3) . ?
C13 H12 0.9500 . ?
N11 C12 1.433(19) . ?
N11 C17 1.51(3) . ?
C12 H13 0.9500 . ?
C17 C18 1.36(4) . ?
C17 C19 1.49(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
B1_1 O2_1 1.5191(18) . ?
B1_1 O1_1 1.5209(18) . ?
O1_1 C1_1 1.3538(17) . ?
C1_1 C6_1 1.382(2) . ?
C1_1 C2_1 1.398(2) . ?
O2_1 C2_1 1.3551(17) . ?
C3_1 C2_1 1.376(2) . ?
C3_1 C4_1 1.407(2) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.376(3) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.402(2) . ?
C5_1 H5_1 0.9500 . ?
C6_1 H6_1 0.9500 . ?
C1_2 N1_2 1.3422(18) . ?
C1_2 N2_2 1.3468(18) . ?
N1_2 C2_2 1.3834(18) . ?
N1_2 C4_2 1.4892(18) . ?
C2_2 C3_2 1.336(2) . ?
C2_2 H2_2 0.9500 . ?
N2_2 C3_2 1.3800(18) . ?
N2_2 C7_2 1.478(3) . ?
N2_2 C17_2 1.65(3) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C6_2 1.515(2) . ?
C4_2 C5_2 1.522(2) . ?
C4_2 H4_2 1.0000 . ?
C5_2 H5A_2 0.9800 . ?
C5_2 H5B_2 0.9800 . ?
C5_2 H5C_2 0.9800 . ?
C6_2 H6A_2 0.9800 . ?
C6_2 H6B_2 0.9800 . ?
C6_2 H6C_2 0.9800 . ?
C7_2 C8_2 1.508(4) . ?
C7_2 C9_2 1.532(4) . ?
C7_2 H7_2 1.0000 . ?
C8_2 H8A_2 0.9800 . ?
C8_2 H8B_2 0.9800 . ?
C8_2 H8C_2 0.9800 . ?
C9_2 H9A_2 0.9800 . ?
C9_2 H9B_2 0.9800 . ?
C9_2 H9C_2 0.9800 . ?
C18_2 C17_2 1.72(4) . ?
C18_2 H18A_2 0.9800 . ?
C18_2 H18B_2 0.9800 . ?
C18_2 H18C_2 0.9800 . ?
C19_2 C17_2 1.39(4) . ?
C19_2 H19A_2 0.9800 . ?
C19_2 H19B_2 0.9800 . ?
C19_2 H19C_2 0.9800 . ?
C17_2 H17_2 1.0000 . ?

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
C13 N2 C4 119.4(14) . . ?
C3 N2 C4 117.11(13) . . ?
C13 N2 B1_1 121.4(14) . . ?
C3 N2 B1_1 118.49(13) . . ?
C4 N2 B1_1 119.08(11) . . ?
N2 C4 C5 112.23(11) . . ?
N2 C4 C6 112.35(12) . . ?
C5 C4 C6 110.67(12) . . ?
N2 C4 H4 107.1 . . ?
C5 C4 H4 107.1 . . ?
C6 C4 H4 107.1 . . ?
N1 C1 C1_2 109.67(13) . . ?
N1 C1 B1_1 115.87(13) . . ?
C1_2 C1 B1_1 110.36(12) . . ?
N1 C1 H1 106.8 . . ?
C1_2 C1 H1 106.8 . . ?
B1_1 C1 H1 106.8 . . ?
C2 C3 N2 125.15(19) . . ?
C2 C3 H2 117.4 . . ?
N2 C3 H2 117.4 . . ?
C2 N1 C1 112.34(12) . . ?
C2 N1 C7 114.66(13) . . ?
C1 N1 C7 113.54(14) . . ?
C3 C2 N1 124.97(16) . . ?
C3 C2 H3 117.5 . . ?
N1 C2 H3 117.5 . . ?
N1 C7 C9 115.76(18) . . ?
N1 C7 C8 110.69(17) . . ?
C9 C7 C8 109.4(2) . . ?
N1 C7 H7 106.9 . . ?
C9 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N11 C11 C1_2 109.2(14) . . ?
N11 C11 B1_1 113.3(14) . . ?
C1_2 C11 B1_1 107.7(13) . . ?
N11 C11 H11 108.9 . . ?
C1_2 C11 H11 108.9 . . ?
B1_1 C11 H11 108.9 . . ?
N2 C13 C12 125(2) . . ?
N2 C13 H12 117.4 . . ?
C12 C13 H12 117.4 . . ?
C12 N11 C11 106.4(13) . . ?
C12 N11 C17 114.5(15) . . ?
C11 N11 C17 116.5(16) . . ?
C13 C12 N11 123.5(19) . . ?
C13 C12 H13 118.3 . . ?
N11 C12 H13 118.3 . . ?
C18 C17 C19 121(3) . . ?
C18 C17 N11 89(2) . . ?
C19 C17 N11 111(2) . . ?
C18 C17 H17 111.4 . . ?
C19 C17 H17 111.4 . . ?
N11 C17 H17 111.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 B1_1 O2_1 112.22(11) . . ?
N2 B1_1 O1_1 113.50(11) . . ?
O2_1 B1_1 O1_1 102.55(11) . . ?
N2 B1_1 C11 105.4(8) . . ?
O2_1 B1_1 C11 123.1(8) . . ?
O1_1 B1_1 C11 99.6(8) . . ?
N2 B1_1 C1 108.36(12) . . ?
O2_1 B1_1 C1 106.31(12) . . ?
O1_1 B1_1 C1 113.64(12) . . ?
C1_1 O1_1 B1_1 107.48(11) . . ?
O1_1 C1_1 C6_1 127.66(14) . . ?
O1_1 C1_1 C2_1 111.14(12) . . ?
C6_1 C1_1 C2_1 121.19(14) . . ?
C2_1 O2_1 B1_1 107.55(11) . . ?
C2_1 C3_1 C4_1 117.85(16) . . ?
C2_1 C3_1 H3_1 121.1 . . ?
C4_1 C3_1 H3_1 121.1 . . ?
C5_1 C4_1 C3_1 120.78(15) . . ?
C5_1 C4_1 H4_1 119.6 . . ?
C3_1 C4_1 H4_1 119.6 . . ?
C4_1 C5_1 C6_1 121.42(15) . . ?
C4_1 C5_1 H5_1 119.3 . . ?
C6_1 C5_1 H5_1 119.3 . . ?
C1_1 C6_1 C5_1 117.52(16) . . ?
C1_1 C6_1 H6_1 121.2 . . ?
C5_1 C6_1 H6_1 121.2 . . ?
O2_1 C2_1 C3_1 127.74(14) . . ?
O2_1 C2_1 C1_1 111.00(12) . . ?
C3_1 C2_1 C1_1 121.24(14) . . ?
N1_2 C1_2 N2_2 107.23(12) . . ?
N1_2 C1_2 C1 124.17(13) . . ?
N2_2 C1_2 C1 128.59(13) . . ?
N1_2 C1_2 C11 143.9(8) . . ?
N2_2 C1_2 C11 108.8(8) . . ?
C1_2 N1_2 C2_2 108.97(12) . . ?
C1_2 N1_2 C4_2 128.00(12) . . ?
C2_2 N1_2 C4_2 123.01(12) . . ?
C3_2 C2_2 N1_2 107.35(13) . . ?
C3_2 C2_2 H2_2 126.3 . . ?
N1_2 C2_2 H2_2 126.3 . . ?
C1_2 N2_2 C3_2 108.88(12) . . ?
C1_2 N2_2 C7_2 126.50(14) . . ?
C3_2 N2_2 C7_2 124.61(14) . . ?
C1_2 N2_2 C17_2 137.1(11) . . ?
C3_2 N2_2 C17_2 113.1(10) . . ?
C2_2 C3_2 N2_2 107.56(13) . . ?
C2_2 C3_2 H3_2 126.2 . . ?
N2_2 C3_2 H3_2 126.2 . . ?
N1_2 C4_2 C6_2 109.98(12) . . ?
N1_2 C4_2 C5_2 109.33(12) . . ?
C6_2 C4_2 C5_2 113.25(13) . . ?
N1_2 C4_2 H4_2 108.0 . . ?
C6_2 C4_2 H4_2 108.0 . . ?
C5_2 C4_2 H4_2 108.0 . . ?
C4_2 C5_2 H5A_2 109.5 . . ?
C4_2 C5_2 H5B_2 109.5 . . ?
H5A_2 C5_2 H5B_2 109.5 . . ?
C4_2 C5_2 H5C_2 109.5 . . ?
H5A_2 C5_2 H5C_2 109.5 . . ?
H5B_2 C5_2 H5C_2 109.5 . . ?
C4_2 C6_2 H6A_2 109.5 . . ?
C4_2 C6_2 H6B_2 109.5 . . ?
H6A_2 C6_2 H6B_2 109.5 . . ?
C4_2 C6_2 H6C_2 109.5 . . ?
H6A_2 C6_2 H6C_2 109.5 . . ?
H6B_2 C6_2 H6C_2 109.5 . . ?
N2_2 C7_2 C8_2 109.96(19) . . ?
N2_2 C7_2 C9_2 109.4(2) . . ?
C8_2 C7_2 C9_2 111.9(2) . . ?
N2_2 C7_2 H7_2 108.5 . . ?
C8_2 C7_2 H7_2 108.5 . . ?
C9_2 C7_2 H7_2 108.5 . . ?
C7_2 C8_2 H8A_2 109.5 . . ?
C7_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
C7_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C7_2 C9_2 H9A_2 109.5 . . ?
C7_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9B_2 109.5 . . ?
C7_2 C9_2 H9C_2 109.5 . . ?
H9A_2 C9_2 H9C_2 109.5 . . ?
H9B_2 C9_2 H9C_2 109.5 . . ?
C17_2 C18_2 H18A_2 109.5 . . ?
C17_2 C18_2 H18B_2 109.5 . . ?
H18A_2 C18_2 H18B_2 109.5 . . ?
C17_2 C18_2 H18C_2 109.5 . . ?
H18A_2 C18_2 H18C_2 109.5 . . ?
H18B_2 C18_2 H18C_2 109.5 . . ?
C17_2 C19_2 H19A_2 109.5 . . ?
C17_2 C19_2 H19B_2 109.5 . . ?
H19A_2 C19_2 H19B_2 109.5 . . ?
C17_2 C19_2 H19C_2 109.5 . . ?
H19A_2 C19_2 H19C_2 109.5 . . ?
H19B_2 C19_2 H19C_2 109.5 . . ?
C19_2 C17_2 N2_2 111(3) . . ?
C19_2 C17_2 C18_2 107(3) . . ?
N2_2 C17_2 C18_2 104(2) . . ?
C19_2 C17_2 H17_2 111.7 . . ?
N2_2 C17_2 H17_2 111.7 . . ?
C18_2 C17_2 H17_2 111.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N2 C4 C5 -86.2(12) . . . . ?
C3 N2 C4 C5 -64.37(17) . . . . ?
B1_1 N2 C4 C5 89.52(15) . . . . ?
C13 N2 C4 C6 39.3(12) . . . . ?
C3 N2 C4 C6 61.11(17) . . . . ?
B1_1 N2 C4 C6 -145.00(13) . . . . ?
C4 N2 C3 C2 164.56(16) . . . . ?
B1_1 N2 C3 C2 10.5(2) . . . . ?
C1_2 C1 N1 C2 -164.61(13) . . . . ?
B1_1 C1 N1 C2 -38.89(19) . . . . ?
C1_2 C1 N1 C7 63.24(18) . . . . ?
B1_1 C1 N1 C7 -171.04(14) . . . . ?
N2 C3 C2 N1 -4.6(3) . . . . ?
C1 N1 C2 C3 19.9(2) . . . . ?
C7 N1 C2 C3 151.47(18) . . . . ?
C2 N1 C7 C9 -63.0(2) . . . . ?
C1 N1 C7 C9 68.0(2) . . . . ?
C2 N1 C7 C8 62.1(2) . . . . ?
C1 N1 C7 C8 -166.88(16) . . . . ?
C4 N2 C13 C12 -172.2(18) . . . . ?
B1_1 N2 C13 C12 12(3) . . . . ?
C1_2 C11 N11 C12 175.1(13) . . . . ?
B1_1 C11 N11 C12 55.0(18) . . . . ?
C1_2 C11 N11 C17 -56(2) . . . . ?
B1_1 C11 N11 C17 -176.0(15) . . . . ?
N2 C13 C12 N11 -5(4) . . . . ?
C11 N11 C12 C13 -30(3) . . . . ?
C17 N11 C12 C13 -160(2) . . . . ?
C12 N11 C17 C18 -61(3) . . . . ?
C11 N11 C17 C18 174(2) . . . . ?
C12 N11 C17 C19 62(3) . . . . ?
C11 N11 C17 C19 -63(3) . . . . ?
C13 N2 B1_1 O2_1 -122.6(13) . . . . ?
C3 N2 B1_1 O2_1 -144.68(13) . . . . ?
C4 N2 B1_1 O2_1 61.78(16) . . . . ?
C13 N2 B1_1 O1_1 121.7(13) . . . . ?
C3 N2 B1_1 O1_1 99.63(15) . . . . ?
C4 N2 B1_1 O1_1 -53.90(16) . . . . ?
C13 N2 B1_1 C11 13.8(15) . . . . ?
C4 N2 B1_1 C11 -161.8(8) . . . . ?
C3 N2 B1_1 C1 -27.60(19) . . . . ?
C4 N2 B1_1 C1 178.86(12) . . . . ?
N11 C11 B1_1 N2 -48.3(15) . . . . ?
C1_2 C11 B1_1 N2 -169.2(9) . . . . ?
N11 C11 B1_1 O2_1 82.0(15) . . . . ?
C1_2 C11 B1_1 O2_1 -38.9(15) . . . . ?
N11 C11 B1_1 O1_1 -166.1(13) . . . . ?
C1_2 C11 B1_1 O1_1 73.0(11) . . . . ?
N1 C1 B1_1 N2 43.20(18) . . . . ?
C1_2 C1 B1_1 N2 168.57(13) . . . . ?
N1 C1 B1_1 O2_1 164.01(13) . . . . ?
C1_2 C1 B1_1 O2_1 -70.62(15) . . . . ?
N1 C1 B1_1 O1_1 -83.95(16) . . . . ?
C1_2 C1 B1_1 O1_1 41.42(18) . . . . ?
N2 B1_1 O1_1 C1_1 116.31(12) . . . . ?
O2_1 B1_1 O1_1 C1_1 -4.97(13) . . . . ?
C11 B1_1 O1_1 C1_1 -132.1(8) . . . . ?
C1 B1_1 O1_1 C1_1 -119.27(13) . . . . ?
B1_1 O1_1 C1_1 C6_1 -175.36(14) . . . . ?
B1_1 O1_1 C1_1 C2_1 3.27(14) . . . . ?
N2 B1_1 O2_1 C2_1 -117.12(12) . . . . ?
O1_1 B1_1 O2_1 C2_1 5.03(13) . . . . ?
C11 B1_1 O2_1 C2_1 115.4(9) . . . . ?
C1 B1_1 O2_1 C2_1 124.58(12) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.3(2) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.2(2) . . . . ?
O1_1 C1_1 C6_1 C5_1 179.01(13) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.5(2) . . . . ?
C4_1 C5_1 C6_1 C1_1 -0.7(2) . . . . ?
B1_1 O2_1 C2_1 C3_1 175.24(14) . . . . ?
B1_1 O2_1 C2_1 C1_1 -3.43(14) . . . . ?
C4_1 C3_1 C2_1 O2_1 -179.03(13) . . . . ?
C4_1 C3_1 C2_1 C1_1 -0.5(2) . . . . ?
O1_1 C1_1 C2_1 O2_1 0.10(16) . . . . ?
C6_1 C1_1 C2_1 O2_1 178.83(12) . . . . ?
O1_1 C1_1 C2_1 C3_1 -178.67(12) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.1(2) . . . . ?
N1 C1 C1_2 N1_2 -131.14(15) . . . . ?
B1_1 C1 C1_2 N1_2 100.05(16) . . . . ?
N1 C1 C1_2 N2_2 49.8(2) . . . . ?
B1_1 C1 C1_2 N2_2 -78.97(19) . . . . ?
N11 C11 C1_2 N1_2 -52(2) . . . . ?
B1_1 C11 C1_2 N1_2 71.4(17) . . . . ?
N11 C11 C1_2 N2_2 131.3(12) . . . . ?
B1_1 C11 C1_2 N2_2 -105.3(10) . . . . ?
N2_2 C1_2 N1_2 C2_2 -0.60(16) . . . . ?
C1 C1_2 N1_2 C2_2 -179.80(13) . . . . ?
C11 C1_2 N1_2 C2_2 -177.4(14) . . . . ?
N2_2 C1_2 N1_2 C4_2 -178.97(12) . . . . ?
C1 C1_2 N1_2 C4_2 1.8(2) . . . . ?
C11 C1_2 N1_2 C4_2 4.3(14) . . . . ?
C1_2 N1_2 C2_2 C3_2 0.10(17) . . . . ?
C4_2 N1_2 C2_2 C3_2 178.57(13) . . . . ?
N1_2 C1_2 N2_2 C3_2 0.86(15) . . . . ?
C1 C1_2 N2_2 C3_2 -179.98(14) . . . . ?
C11 C1_2 N2_2 C3_2 178.9(8) . . . . ?
N1_2 C1_2 N2_2 C7_2 179.78(16) . . . . ?
C1 C1_2 N2_2 C7_2 -1.1(2) . . . . ?
N1_2 C1_2 N2_2 C17_2 -166.7(17) . . . . ?
C11 C1_2 N2_2 C17_2 11.3(19) . . . . ?
N1_2 C2_2 C3_2 N2_2 0.42(17) . . . . ?
C1_2 N2_2 C3_2 C2_2 -0.81(17) . . . . ?
C7_2 N2_2 C3_2 C2_2 -179.75(16) . . . . ?
C17_2 N2_2 C3_2 C2_2 170.0(13) . . . . ?
C1_2 N1_2 C4_2 C6_2 -123.08(15) . . . . ?
C2_2 N1_2 C4_2 C6_2 58.76(17) . . . . ?
C1_2 N1_2 C4_2 C5_2 111.99(16) . . . . ?
C2_2 N1_2 C4_2 C5_2 -66.17(18) . . . . ?
C1_2 N2_2 C7_2 C8_2 -111.79(19) . . . . ?
C3_2 N2_2 C7_2 C8_2 67.0(2) . . . . ?
C1_2 N2_2 C7_2 C9_2 125.0(2) . . . . ?
C3_2 N2_2 C7_2 C9_2 -56.3(3) . . . . ?
C1_2 N2_2 C17_2 C19_2 118(2) . . . . ?
C3_2 N2_2 C17_2 C19_2 -50(3) . . . . ?
C1_2 N2_2 C17_2 C18_2 -128.0(15) . . . . ?
C3_2 N2_2 C17_2 C18_2 64.8(18) . . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.035

_shelxl_version_number           2014/6

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

data_ae154_a
_database_code_depnum_ccdc_archive 'CCDC 1529582'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H40 B2 N4 O4'
_chemical_formula_sum            'C22 H40 B2 N4 O4'
_chemical_formula_weight         446.20

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.9858(13)
_cell_length_b                   15.1342(19)
_cell_length_c                   16.584(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.132(4)
_cell_angle_gamma                90
_cell_volume                     2505.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6047
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      23.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.23
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17394
_diffrn_reflns_av_unetI/netI     0.1263
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4820
_reflns_number_gt                2392
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0386P)²+2.2677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4820
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5993(2) 0.60894(14) 0.32000(14) 0.0369(6) Uani 1 1 d . . . . .
C1 C 0.7971(3) 0.6319(2) 0.2299(2) 0.0255(8) Uani 1 1 d . . . . .
B1 B 0.6635(4) 0.5747(2) 0.2484(2) 0.0250(9) Uani 1 1 d . . . . .
N1 N 0.8067(2) 0.67426(17) 0.16077(16) 0.0252(7) Uani 1 1 d . . . . .
C2 C 0.7100(3) 0.6669(2) 0.0981(2) 0.0272(8) Uani 1 1 d . . . . .
H2 H 0.7253 0.6948 0.0478 0.033 Uiso 1 1 calc R U . . .
O2 O 0.8515(3) 0.73153(15) 0.34417(15) 0.0496(8) Uani 1 1 d . . . . .
B2 B 0.8980(4) 0.6492(3) 0.3072(2) 0.0342(11) Uani 1 1 d . . . . .
N2 N 0.5672(2) 0.57546(16) 0.17512(17) 0.0271(7) Uani 1 1 d . . . . .
O4 O 0.8910(2) 0.57306(14) 0.36198(13) 0.0351(6) Uani 1 1 d . . . . .
N4 N 0.6779(2) 0.41798(16) 0.33000(17) 0.0253(7) Uani 1 1 d . . . . .
C4 C 0.9197(3) 0.7361(2) 0.1433(2) 0.0335(9) Uani 1 1 d . . . . .
H4 H 0.9853 0.7319 0.1895 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5959(3) 0.6208(2) 0.1086(2) 0.0280(9) Uani 1 1 d . . . . .
H3 H 0.5315 0.6207 0.0657 0.034 Uiso 1 1 calc R U . . .
O3 O 1.0425(2) 0.66046(16) 0.29102(15) 0.0490(8) Uani 1 1 d . . . . .
N3 N 0.7773(3) 0.42026(17) 0.21598(16) 0.0256(7) Uani 1 1 d . . . . .
C5 C 0.8686(4) 0.8305(2) 0.1408(2) 0.0428(10) Uani 1 1 d . . . . .
H00S H 0.9448 0.8713 0.1389 0.064 Uiso 1 1 calc R U . . .
H00T H 0.8167 0.8425 0.1891 0.064 Uiso 1 1 calc R U . . .
H00U H 0.8115 0.8389 0.0927 0.064 Uiso 1 1 calc R U . . .
C6 C 0.9924(4) 0.7093(3) 0.0682(2) 0.0459(11) Uani 1 1 d . . . . .
H00V H 0.9332 0.7175 0.0209 0.069 Uiso 1 1 calc R U . . .
H00W H 1.0185 0.6470 0.0723 0.069 Uiso 1 1 calc R U . . .
H00X H 1.0726 0.7459 0.0626 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3236(3) 0.6059(2) 0.1752(2) 0.0417(10) Uani 1 1 d . . . . .
H00N H 0.3223 0.6313 0.1208 0.063 Uiso 1 1 calc R U . . .
H00O H 0.3412 0.6526 0.2148 0.063 Uiso 1 1 calc R U . . .
H00P H 0.2367 0.5786 0.1856 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4333(3) 0.5361(2) 0.1816(2) 0.0354(9) Uani 1 1 d . . . . .
H7 H 0.4282 0.5097 0.2368 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4084(4) 0.4622(2) 0.1220(3) 0.0697(15) Uani 1 1 d . . . . .
H015 H 0.4149 0.4852 0.0670 0.105 Uiso 1 1 calc R U . . .
H016 H 0.3188 0.4377 0.1297 0.105 Uiso 1 1 calc R U . . .
H017 H 0.4755 0.4157 0.1306 0.105 Uiso 1 1 calc R U . . .
C17 C 0.4860(5) 0.3779(3) 0.4110(3) 0.0925(19) Uani 1 1 d . . . . .
H01B H 0.4292 0.3816 0.3622 0.139 Uiso 1 1 calc R U . . .
H01C H 0.4337 0.3947 0.4579 0.139 Uiso 1 1 calc R U . . .
H01D H 0.5186 0.3173 0.4177 0.139 Uiso 1 1 calc R U . . .
C20 C 0.7297(5) 0.7290(2) 0.3846(2) 0.0528(13) Uani 1 1 d . . . . .
H00Y H 0.7132 0.7885 0.4072 0.063 Uiso 1 1 calc R U . . .
H00Z H 0.7399 0.6877 0.4306 0.063 Uiso 1 1 calc R U . . .
C21 C 1.0141(4) 0.5734(2) 0.4043(2) 0.0402(10) Uani 1 1 d . . . . .
H00B H 1.0374 0.5131 0.4231 0.048 Uiso 1 1 calc R U . . .
H21 H 1.0101 0.6130 0.4517 0.048 Uiso 1 1 calc R U . . .
C22 C 1.1153(4) 0.6062(3) 0.3460(2) 0.0522(12) Uani 1 1 d . . . . .
H013 H 1.1862 0.6406 0.3743 0.063 Uiso 1 1 calc R U . . .
H014 H 1.1574 0.5562 0.3175 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6033(3) 0.4397(2) 0.4033(2) 0.0308(9) Uani 1 1 d . . . . .
H16 H 0.5678 0.5012 0.3975 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7843(4) 0.3838(3) 0.0722(2) 0.0502(11) Uani 1 1 d . . . . .
H010 H 0.8108 0.4063 0.0194 0.075 Uiso 1 1 calc R U . . .
H011 H 0.6865 0.3790 0.0736 0.075 Uiso 1 1 calc R U . . .
H012 H 0.8244 0.3255 0.0813 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7346(3) 0.3358(2) 0.3189(2) 0.0344(9) Uani 1 1 d . . . . .
H12 H 0.7300 0.2872 0.3549 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7970(3) 0.3369(2) 0.2483(2) 0.0328(9) Uani 1 1 d . . . . .
H11 H 0.8455 0.2896 0.2250 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7050(3) 0.4711(2) 0.2666(2) 0.0235(8) Uani 1 1 d . . . . .
C14 C 0.9842(3) 0.4514(2) 0.1442(2) 0.0400(10) Uani 1 1 d . . . . .
H14 H 1.0200 0.4724 0.0931 0.060 Uiso 1 1 calc R U . . .
H00L H 1.0200 0.3924 0.1562 0.060 Uiso 1 1 calc R U . . .
H00M H 1.0106 0.4921 0.1876 0.060 Uiso 1 1 calc R U . . .
C13 C 0.8327(3) 0.4469(2) 0.1378(2) 0.0313(9) Uani 1 1 d . . . . .
H13 H 0.7984 0.5074 0.1243 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6952(4) 0.4372(3) 0.4754(2) 0.0677(14) Uani 1 1 d . . . . .
H018 H 0.7325 0.3776 0.4815 0.102 Uiso 1 1 calc R U . . .
H019 H 0.6454 0.4527 0.5237 0.102 Uiso 1 1 calc R U . . .
H01A H 0.7682 0.4796 0.4682 0.102 Uiso 1 1 calc R U . . .
C19 C 0.6056(4) 0.7016(2) 0.3355(2) 0.0478(11) Uani 1 1 d . . . . .
H00Q H 0.5247 0.7195 0.3650 0.057 Uiso 1 1 calc R U . . .
H00R H 0.6049 0.7337 0.2835 0.057 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
O1 C19 1.427(4) . ?
O1 B1 1.457(4) . ?
C1 N1 1.319(4) . ?
C1 B1 1.624(5) . ?
C1 B2 1.636(5) . ?
B1 N2 1.534(4) . ?
B1 C10 1.649(5) . ?
N1 C2 1.409(4) . ?
N1 C4 1.499(4) . ?
C2 C3 1.350(4) . ?
C2 H2 0.9500 . ?
O2 C20 1.401(5) . ?
O2 B2 1.468(5) . ?
B2 O4 1.470(4) . ?
B2 O3 1.483(5) . ?
N2 C3 1.335(4) . ?
N2 C7 1.470(4) . ?
O4 C21 1.403(4) . ?
N4 C10 1.355(4) . ?
N4 C12 1.380(4) . ?
N4 C16 1.476(4) . ?
C4 C6 1.510(5) . ?
C4 C5 1.517(5) . ?
C4 H4 1.0000 . ?
C3 H3 0.9500 . ?
O3 C22 1.417(4) . ?
N3 C10 1.357(4) . ?
N3 C11 1.384(4) . ?
N3 C13 1.477(4) . ?
C5 H00S 0.9800 . ?
C5 H00T 0.9800 . ?
C5 H00U 0.9800 . ?
C6 H00V 0.9800 . ?
C6 H00W 0.9800 . ?
C6 H00X 0.9800 . ?
C8 C7 1.524(4) . ?
C8 H00N 0.9800 . ?
C8 H00O 0.9800 . ?
C8 H00P 0.9800 . ?
C7 C9 1.511(5) . ?
C7 H7 1.0000 . ?
C9 H015 0.9800 . ?
C9 H016 0.9800 . ?
C9 H017 0.9800 . ?
C17 C16 1.506(5) . ?
C17 H01B 0.9800 . ?
C17 H01C 0.9800 . ?
C17 H01D 0.9800 . ?
C20 C19 1.526(5) . ?
C20 H00Y 0.9900 . ?
C20 H00Z 0.9900 . ?
C21 C22 1.496(5) . ?
C21 H00B 0.9900 . ?
C21 H21 0.9900 . ?
C22 H013 0.9900 . ?
C22 H014 0.9900 . ?
C16 C18 1.493(5) . ?
C16 H16 1.0000 . ?
C15 C13 1.519(4) . ?
C15 H010 0.9800 . ?
C15 H011 0.9800 . ?
C15 H012 0.9800 . ?
C12 C11 1.337(5) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C14 C13 1.516(4) . ?
C14 H14 0.9800 . ?
C14 H00L 0.9800 . ?
C14 H00M 0.9800 . ?
C13 H13 1.0000 . ?
C18 H018 0.9800 . ?
C18 H019 0.9800 . ?
C18 H01A 0.9800 . ?
C19 H00Q 0.9900 . ?
C19 H00R 0.9900 . ?

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
C19 O1 B1 118.5(3) . . ?
N1 C1 B1 119.8(3) . . ?
N1 C1 B2 123.4(3) . . ?
B1 C1 B2 115.7(3) . . ?
O1 B1 N2 111.3(3) . . ?
O1 B1 C1 109.9(3) . . ?
N2 B1 C1 110.6(3) . . ?
O1 B1 C10 107.6(3) . . ?
N2 B1 C10 107.6(2) . . ?
C1 B1 C10 109.7(3) . . ?
C1 N1 C2 122.9(3) . . ?
C1 N1 C4 122.6(2) . . ?
C2 N1 C4 114.5(3) . . ?
C3 C2 N1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
N1 C2 H2 119.6 . . ?
C20 O2 B2 117.5(3) . . ?
O2 B2 O4 112.8(3) . . ?
O2 B2 O3 107.2(3) . . ?
O4 B2 O3 105.1(3) . . ?
O2 B2 C1 105.5(3) . . ?
O4 B2 C1 108.8(3) . . ?
O3 B2 C1 117.6(3) . . ?
C3 N2 C7 118.6(3) . . ?
C3 N2 B1 121.1(3) . . ?
C7 N2 B1 119.7(3) . . ?
C21 O4 B2 104.7(3) . . ?
C10 N4 C12 110.0(3) . . ?
C10 N4 C16 128.3(3) . . ?
C12 N4 C16 121.7(3) . . ?
N1 C4 C6 111.6(3) . . ?
N1 C4 C5 109.9(3) . . ?
C6 C4 C5 113.4(3) . . ?
N1 C4 H4 107.2 . . ?
C6 C4 H4 107.2 . . ?
C5 C4 H4 107.2 . . ?
N2 C3 C2 124.6(3) . . ?
N2 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?
C22 O3 B2 107.8(3) . . ?
C10 N3 C11 110.5(3) . . ?
C10 N3 C13 127.0(3) . . ?
C11 N3 C13 122.5(3) . . ?
C4 C5 H00S 109.5 . . ?
C4 C5 H00T 109.5 . . ?
H00S C5 H00T 109.5 . . ?
C4 C5 H00U 109.5 . . ?
H00S C5 H00U 109.5 . . ?
H00T C5 H00U 109.5 . . ?
C4 C6 H00V 109.5 . . ?
C4 C6 H00W 109.5 . . ?
H00V C6 H00W 109.5 . . ?
C4 C6 H00X 109.5 . . ?
H00V C6 H00X 109.5 . . ?
H00W C6 H00X 109.5 . . ?
C7 C8 H00N 109.5 . . ?
C7 C8 H00O 109.5 . . ?
H00N C8 H00O 109.5 . . ?
C7 C8 H00P 109.5 . . ?
H00N C8 H00P 109.5 . . ?
H00O C8 H00P 109.5 . . ?
N2 C7 C9 112.9(3) . . ?
N2 C7 C8 111.6(3) . . ?
C9 C7 C8 111.0(3) . . ?
N2 C7 H7 107.0 . . ?
C9 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C7 C9 H015 109.5 . . ?
C7 C9 H016 109.5 . . ?
H015 C9 H016 109.5 . . ?
C7 C9 H017 109.5 . . ?
H015 C9 H017 109.5 . . ?
H016 C9 H017 109.5 . . ?
C16 C17 H01B 109.5 . . ?
C16 C17 H01C 109.5 . . ?
H01B C17 H01C 109.5 . . ?
C16 C17 H01D 109.5 . . ?
H01B C17 H01D 109.5 . . ?
H01C C17 H01D 109.5 . . ?
O2 C20 C19 117.1(3) . . ?
O2 C20 H00Y 108.0 . . ?
C19 C20 H00Y 108.0 . . ?
O2 C20 H00Z 108.0 . . ?
C19 C20 H00Z 108.0 . . ?
H00Y C20 H00Z 107.3 . . ?
O4 C21 C22 105.9(3) . . ?
O4 C21 H00B 110.6 . . ?
C22 C21 H00B 110.6 . . ?
O4 C21 H21 110.6 . . ?
C22 C21 H21 110.6 . . ?
H00B C21 H21 108.7 . . ?
O3 C22 C21 105.3(3) . . ?
O3 C22 H013 110.7 . . ?
C21 C22 H013 110.7 . . ?
O3 C22 H014 110.7 . . ?
C21 C22 H014 110.7 . . ?
H013 C22 H014 108.8 . . ?
N4 C16 C18 109.9(3) . . ?
N4 C16 C17 109.7(3) . . ?
C18 C16 C17 112.6(4) . . ?
N4 C16 H16 108.2 . . ?
C18 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C13 C15 H010 109.5 . . ?
C13 C15 H011 109.5 . . ?
H010 C15 H011 109.5 . . ?
C13 C15 H012 109.5 . . ?
H010 C15 H012 109.5 . . ?
H011 C15 H012 109.5 . . ?
C11 C12 N4 107.8(3) . . ?
C11 C12 H12 126.1 . . ?
N4 C12 H12 126.1 . . ?
C12 C11 N3 106.5(3) . . ?
C12 C11 H11 126.7 . . ?
N3 C11 H11 126.7 . . ?
N4 C10 N3 105.1(3) . . ?
N4 C10 B1 130.8(3) . . ?
N3 C10 B1 124.1(3) . . ?
C13 C14 H14 109.5 . . ?
C13 C14 H00L 109.5 . . ?
H14 C14 H00L 109.5 . . ?
C13 C14 H00M 109.5 . . ?
H14 C14 H00M 109.5 . . ?
H00L C14 H00M 109.5 . . ?
N3 C13 C14 109.9(3) . . ?
N3 C13 C15 109.7(3) . . ?
C14 C13 C15 112.4(3) . . ?
N3 C13 H13 108.2 . . ?
C14 C13 H13 108.2 . . ?
C15 C13 H13 108.2 . . ?
C16 C18 H018 109.5 . . ?
C16 C18 H019 109.5 . . ?
H018 C18 H019 109.5 . . ?
C16 C18 H01A 109.5 . . ?
H018 C18 H01A 109.5 . . ?
H019 C18 H01A 109.5 . . ?
O1 C19 C20 113.3(3) . . ?
O1 C19 H00Q 108.9 . . ?
C20 C19 H00Q 108.9 . . ?
O1 C19 H00R 108.9 . . ?
C20 C19 H00R 108.9 . . ?
H00Q C19 H00R 107.7 . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

