# 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_AVDPy
_database_code_depnum_ccdc_archive 'CCDC 1527279'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        2,3-Dihydroxypyrazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N2 O2'
_chemical_formula_sum            'C4 H4 N2 O2'
_chemical_formula_weight         112.09

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

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

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

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

_cell_length_a                   6.1105(3)
_cell_length_b                   10.2259(5)
_cell_length_c                   6.9669(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.973(2)
_cell_angle_gamma                90
_cell_volume                     434.28(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8935
_cell_measurement_theta_min      3.3420
_cell_measurement_theta_max      27.1208

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7133
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            14626
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         27.121
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             957
_reflns_number_gt                882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR2014 (M. C. Burla, R. Caliandro, B. Carrozzini, G. L. Cascarano, 
C. Cuocci, C. Giacovazzo, M. Mallamo, A. Mazzone and G. Polidori, 
J. Appl. Cryst. 2015, 48, 306-309.)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, 
Kreuzherrenstr. 102, 53227 Bonn, Germany)
;

_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
;
_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)+(0.0534P)²+0.1961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         957
_refine_ls_number_parameters     81
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42284(18) 0.80162(11) 0.22124(15) 0.0106(3) Uani 1 1 d . . . . .
C2 C 0.24075(17) 0.88962(11) 0.13935(15) 0.0100(3) Uani 1 1 d . . . . .
C3 C 0.01732(18) 0.69713(11) 0.08111(16) 0.0119(3) Uani 1 1 d . . . . .
H3 H -0.1202 0.6615 0.0357 0.014 Uiso 1 1 calc R U . . .
C4 C 0.17935(18) 0.61853(11) 0.14883(16) 0.0119(3) Uani 1 1 d . . . . .
H4 H 0.1584 0.5265 0.1497 0.014 Uiso 1 1 calc R U . . .
N1 N 0.37839(15) 0.67167(10) 0.21788(14) 0.0112(2) Uani 1 1 d . . . . .
N2 N 0.05145(15) 0.83105(9) 0.07763(14) 0.0106(2) Uani 1 1 d . . . . .
O1 O 0.59849(13) 0.84814(8) 0.28437(12) 0.0158(2) Uani 1 1 d . . . . .
O2 O 0.26816(13) 1.00954(8) 0.12927(12) 0.0130(2) Uani 1 1 d . . . . .
H1 H 0.483(3) 0.6158(16) 0.261(2) 0.022(4) Uiso 1 1 d . . . . .
H2 H -0.058(3) 0.8831(17) 0.020(2) 0.023(4) Uiso 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 1.2273(13) . ?
C1 N1 1.3562(15) . ?
C1 C2 1.5117(15) . ?
C2 O2 1.2403(14) . ?
C2 N2 1.3463(14) . ?
C3 C4 1.3357(15) . ?
C3 N2 1.3857(14) . ?
C3 H3 0.9500 . ?
C4 N1 1.3874(14) . ?
C4 H4 0.9500 . ?
N1 H1 0.895(18) . ?
N2 H2 0.926(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 123.71(10) . . ?
O1 C1 C2 120.47(10) . . ?
N1 C1 C2 115.82(10) . . ?
O2 C2 N2 122.56(10) . . ?
O2 C2 C1 120.74(10) . . ?
N2 C2 C1 116.70(10) . . ?
C4 C3 N2 119.48(10) . . ?
C4 C3 H3 120.3 . . ?
N2 C3 H3 120.3 . . ?
C3 C4 N1 119.82(10) . . ?
C3 C4 H4 120.1 . . ?
N1 C4 H4 120.1 . . ?
C1 N1 C4 124.02(10) . . ?
C1 N1 H1 118.8(11) . . ?
C4 N1 H1 117.1(11) . . ?
C2 N2 C3 124.13(10) . . ?
C2 N2 H2 117.6(10) . . ?
C3 N2 H2 118.1(10) . . ?

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 2.21(16) . . . . ?
N1 C1 C2 O2 -177.29(10) . . . . ?
O1 C1 C2 N2 -178.36(10) . . . . ?
N1 C1 C2 N2 2.14(14) . . . . ?
N2 C3 C4 N1 1.10(16) . . . . ?
O1 C1 N1 C4 179.21(10) . . . . ?
C2 C1 N1 C4 -1.31(15) . . . . ?
C3 C4 N1 C1 -0.31(16) . . . . ?
O2 C2 N2 C3 177.91(10) . . . . ?
C1 C2 N2 C3 -1.51(15) . . . . ?
C4 C3 N2 C2 -0.12(17) . . . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054

_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_lhf172
_database_code_depnum_ccdc_archive 'CCDC 1484824'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'
_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 H16 B F2 Li N8 O2'
_chemical_formula_sum            'C10 H16 B F2 Li N8 O2'
_chemical_formula_weight         336.06

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

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

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

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

_cell_length_a                   8.1367(13)
_cell_length_b                   9.2057(16)
_cell_length_c                   11.0783(17)
_cell_angle_alpha                107.287(13)
_cell_angle_beta                 101.500(13)
_cell_angle_gamma                97.456(13)
_cell_volume                     760.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4437
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            6652
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.989
_diffrn_reflns_theta_max         26.828
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3209
_reflns_number_gt                1528
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R.
(2005). J. Appl. Cryst. 38, 381-388.)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
Ortep-3 for Windows (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 
102, 53227 Bonn, Germany)
;

_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
ShelXle (C. B. Huebschle, G. M. Sheldrick, B. Dittrich, J. Appl. Cryst. 
2011, 44, 1281-1284)
;
_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)+(0.0361P)²] 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         3209
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_restrained_S_all      0.762
_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 0.1251(3) 0.8729(3) 0.6291(2) 0.0478(5) Uani 1 1 d . . . . .
C2 C 0.0325(3) 0.7573(2) 0.5027(2) 0.0479(5) Uani 1 1 d . . . . .
C3 C 0.1037(3) 0.7214(3) 1.0853(2) 0.0620(7) Uani 1 1 d . . . . .
H3A H 0.0019 0.6452 1.0791 0.074 Uiso 1 1 calc R U . . .
H3B H 0.0768 0.8265 1.1103 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2575(3) 0.7140(3) 1.1861(2) 0.0615(6) Uani 1 1 d . . . . .
H4A H 0.3257 0.8191 1.2385 0.074 Uiso 1 1 calc R U . . .
H4B H 0.2208 0.6620 1.2456 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3586(3) 0.6189(3) 1.1026(2) 0.0593(6) Uani 1 1 d . . . . .
H5A H 0.4819 0.6437 1.1476 0.071 Uiso 1 1 calc R U . . .
H5B H 0.3143 0.5061 1.0786 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3280(3) 0.6707(3) 0.9856(2) 0.0662(7) Uani 1 1 d . . . . .
H6A H 0.4044 0.7716 1.0034 0.079 Uiso 1 1 calc R U . . .
H6B H 0.3481 0.5930 0.9093 0.079 Uiso 1 1 calc R U . . .
C7 C -0.3499(3) 0.6029(3) 0.6565(2) 0.0566(6) Uani 1 1 d . . . . .
H7A H -0.3927 0.4919 0.6421 0.068 Uiso 1 1 calc R U . . .
H7B H -0.3138 0.6117 0.5783 0.068 Uiso 1 1 calc R U . . .
C8 C -0.4877(3) 0.6956(3) 0.6823(2) 0.0660(7) Uani 1 1 d . . . . .
H8A H -0.5502 0.7092 0.6013 0.079 Uiso 1 1 calc R U . . .
H8B H -0.5705 0.6444 0.7188 0.079 Uiso 1 1 calc R U . . .
C9 C -0.3886(3) 0.8487(3) 0.7799(2) 0.0677(7) Uani 1 1 d . . . . .
H9A H -0.4610 0.9019 0.8334 0.081 Uiso 1 1 calc R U . . .
H9B H -0.3414 0.9178 0.7362 0.081 Uiso 1 1 calc R U . . .
C10 C -0.2470(3) 0.8011(3) 0.8622(2) 0.0642(7) Uani 1 1 d . . . . .
H10A H -0.1450 0.8865 0.9019 0.077 Uiso 1 1 calc R U . . .
H10B H -0.2862 0.7723 0.9326 0.077 Uiso 1 1 calc R U . . .
Li1 Li 0.0292(5) 0.6601(4) 0.7886(4) 0.0535(9) Uani 1 1 d . . . . .
B1 B 0.2333(4) 1.1110(3) 0.5556(3) 0.0527(7) Uani 1 1 d . . . . .
N1 N 0.2072(2) 1.0177(2) 0.65079(17) 0.0481(5) Uani 1 1 d . . . . .
N2 N 0.2714(2) 1.0827(2) 0.78204(19) 0.0547(5) Uani 1 1 d . . . . .
N3 N 0.2286(2) 0.9793(2) 0.83501(18) 0.0546(5) Uani 1 1 d . . . . .
N4 N 0.1367(2) 0.8452(2) 0.74103(18) 0.0511(5) Uani 1 1 d . . . . .
N5 N 0.0815(2) 0.6270(2) 0.44871(18) 0.0504(5) Uani 1 1 d . . . . .
N6 N -0.0416(2) 0.5522(2) 0.33684(18) 0.0521(5) Uani 1 1 d . . . . .
N7 N -0.1612(2) 0.6322(2) 0.32231(18) 0.0523(5) Uani 1 1 d . . . . .
N8 N -0.1175(2) 0.76274(19) 0.42704(17) 0.0476(5) Uani 1 1 d . . . . .
F1 F 0.17387(15) 1.00946(13) 0.43071(12) 0.0530(3) Uani 1 1 d . . . . .
F2 F 0.39973(16) 1.18490(14) 0.58701(12) 0.0585(4) Uani 1 1 d . . . . .
O1 O 0.1497(2) 0.68553(19) 0.96215(15) 0.0603(4) Uani 1 1 d . . . . .
O2 O -0.20837(19) 0.66835(17) 0.77134(15) 0.0582(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.326(3) . ?
C1 N1 1.340(3) . ?
C1 C2 1.465(3) . ?
C2 N5 1.322(2) . ?
C2 N8 1.352(3) . ?
C3 O1 1.442(3) . ?
C3 C4 1.526(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.496(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O1 1.453(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.445(3) . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.502(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2 1.449(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
Li1 O1 1.906(4) . ?
Li1 O2 1.918(4) . ?
Li1 N6 2.063(4) 2_566 ?
Li1 N4 2.068(4) . ?
B1 F2 1.360(3) . ?
B1 F1 1.367(3) . ?
B1 N1 1.574(3) . ?
B1 N8 1.581(3) 2_576 ?
N1 N2 1.358(2) . ?
N2 N3 1.303(2) . ?
N3 N4 1.361(2) . ?
N5 N6 1.353(2) . ?
N6 N7 1.307(2) . ?
N6 Li1 2.063(4) 2_566 ?
N7 N8 1.346(2) . ?
N8 B1 1.581(3) 2_576 ?

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
N4 C1 N1 110.27(19) . . ?
N4 C1 C2 122.7(2) . . ?
N1 C1 C2 127.0(2) . . ?
N5 C2 N8 109.82(18) . . ?
N5 C2 C1 124.1(2) . . ?
N8 C2 C1 126.04(19) . . ?
O1 C3 C4 106.83(19) . . ?
O1 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
O1 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 103.07(19) . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C6 C5 C4 101.63(19) . . ?
C6 C5 H5A 111.4 . . ?
C4 C5 H5A 111.4 . . ?
C6 C5 H5B 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.3 . . ?
O1 C6 C5 104.9(2) . . ?
O1 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
O1 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.8 . . ?
O2 C7 C8 106.14(18) . . ?
O2 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O2 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C9 C8 C7 103.3(2) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C8 C9 C10 102.6(2) . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C10 C9 H9B 111.2 . . ?
H9A C9 H9B 109.2 . . ?
O2 C10 C9 104.60(19) . . ?
O2 C10 H10A 110.8 . . ?
C9 C10 H10A 110.8 . . ?
O2 C10 H10B 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
O1 Li1 O2 113.3(2) . . ?
O1 Li1 N6 109.90(18) . 2_566 ?
O2 Li1 N6 107.36(19) . 2_566 ?
O1 Li1 N4 107.25(19) . . ?
O2 Li1 N4 106.15(18) . . ?
N6 Li1 N4 112.89(18) 2_566 . ?
F2 B1 F1 114.9(2) . . ?
F2 B1 N1 109.9(2) . . ?
F1 B1 N1 107.57(19) . . ?
F2 B1 N8 108.59(19) . 2_576 ?
F1 B1 N8 107.5(2) . 2_576 ?
N1 B1 N8 108.20(18) . 2_576 ?
C1 N1 N2 106.46(17) . . ?
C1 N1 B1 131.95(19) . . ?
N2 N1 B1 121.59(18) . . ?
N3 N2 N1 107.80(17) . . ?
N2 N3 N4 110.17(18) . . ?
C1 N4 N3 105.31(18) . . ?
C1 N4 Li1 133.02(19) . . ?
N3 N4 Li1 121.38(18) . . ?
C2 N5 N6 105.02(17) . . ?
N7 N6 N5 111.23(17) . . ?
N7 N6 Li1 127.09(18) . 2_566 ?
N5 N6 Li1 121.68(17) . 2_566 ?
N6 N7 N8 106.87(18) . . ?
N7 N8 C2 107.06(16) . . ?
N7 N8 B1 121.55(19) . 2_576 ?
C2 N8 B1 131.39(17) . 2_576 ?
C3 O1 C6 108.00(17) . . ?
C3 O1 Li1 133.61(17) . . ?
C6 O1 Li1 118.38(17) . . ?
C7 O2 C10 109.64(16) . . ?
C7 O2 Li1 129.01(17) . . ?
C10 O2 Li1 116.49(18) . . ?

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
N4 C1 C2 N5 -67.4(3) . . . . ?
N1 C1 C2 N5 113.1(3) . . . . ?
N4 C1 C2 N8 109.3(3) . . . . ?
N1 C1 C2 N8 -70.2(3) . . . . ?
O1 C3 C4 C5 -19.2(3) . . . . ?
C3 C4 C5 C6 35.1(2) . . . . ?
C4 C5 C6 O1 -39.1(2) . . . . ?
O2 C7 C8 C9 24.9(2) . . . . ?
C7 C8 C9 C10 -35.9(3) . . . . ?
C8 C9 C10 O2 34.3(2) . . . . ?
N4 C1 N1 N2 -0.4(2) . . . . ?
C2 C1 N1 N2 179.1(2) . . . . ?
N4 C1 N1 B1 -179.6(2) . . . . ?
C2 C1 N1 B1 -0.1(4) . . . . ?
F2 B1 N1 C1 -134.2(2) . . . . ?
F1 B1 N1 C1 -8.5(3) . . . . ?
N8 B1 N1 C1 107.3(2) 2_576 . . . ?
F2 B1 N1 N2 46.7(3) . . . . ?
F1 B1 N1 N2 172.50(17) . . . . ?
N8 B1 N1 N2 -71.7(2) 2_576 . . . ?
C1 N1 N2 N3 0.2(2) . . . . ?
B1 N1 N2 N3 179.43(18) . . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N1 C1 N4 N3 0.5(2) . . . . ?
C2 C1 N4 N3 -179.02(19) . . . . ?
N1 C1 N4 Li1 174.11(19) . . . . ?
C2 C1 N4 Li1 -5.4(3) . . . . ?
N2 N3 N4 C1 -0.4(2) . . . . ?
N2 N3 N4 Li1 -174.91(17) . . . . ?
N8 C2 N5 N6 0.5(2) . . . . ?
C1 C2 N5 N6 177.7(2) . . . . ?
C2 N5 N6 N7 -0.1(2) . . . . ?
C2 N5 N6 Li1 179.62(19) . . . 2_566 ?
N5 N6 N7 N8 -0.4(2) . . . . ?
Li1 N6 N7 N8 179.97(19) 2_566 . . . ?
N6 N7 N8 C2 0.6(2) . . . . ?
N6 N7 N8 B1 -179.60(18) . . . 2_576 ?
N5 C2 N8 N7 -0.7(2) . . . . ?
C1 C2 N8 N7 -177.8(2) . . . . ?
N5 C2 N8 B1 179.6(2) . . . 2_576 ?
C1 C2 N8 B1 2.4(4) . . . 2_576 ?
C4 C3 O1 C6 -5.1(3) . . . . ?
C4 C3 O1 Li1 176.3(2) . . . . ?
C5 C6 O1 C3 28.0(3) . . . . ?
C5 C6 O1 Li1 -153.08(19) . . . . ?
C8 C7 O2 C10 -3.4(2) . . . . ?
C8 C7 O2 Li1 -157.4(2) . . . . ?
C9 C10 O2 C7 -19.4(2) . . . . ?
C9 C10 O2 Li1 138.2(2) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.041

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'THF, diethyl ether'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_AVDPySiMe3
_database_code_depnum_ccdc_archive 'CCDC 1527278'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        2,3-Bis(trimethylsilyloxy)pyrazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H20 N2 O2 Si2'
_chemical_formula_sum            'C10 H20 N2 O2 Si2'
_chemical_formula_weight         256.46

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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2602(6)
_cell_length_b                   11.0540(5)
_cell_length_c                   23.4337(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2916.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.5087
_cell_measurement_theta_max      27.1559

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            49784
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.509
_diffrn_reflns_theta_max         27.156
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3235
_reflns_number_gt                2766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR2014 (M. C. Burla, R. Caliandro, B. Carrozzini, G. L. Cascarano, 
C. Cuocci, C. Giacovazzo, M. Mallamo, A. Mazzone and G. Polidori, 
J. Appl. Cryst. 2015, 48, 306-309.)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, 
Kreuzherrenstr. 102, 53227 Bonn, Germany)
;
_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
;
_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)+(0.0391P)²+0.8716P] 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         3235
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0702
_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 0.33938(9) 0.36505(10) 0.07279(5) 0.0108(2) Uani 1 1 d . . . . .
C2 C 0.37454(9) 0.35617(10) 0.13102(5) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.26532(11) 0.52374(12) 0.15037(5) 0.0197(3) Uani 1 1 d . . . . .
H3 H 0.2382 0.5829 0.1767 0.024 Uiso 1 1 calc R U . . .
C4 C 0.22860(11) 0.53048(11) 0.09504(5) 0.0180(3) Uani 1 1 d . . . . .
H4 H 0.1750 0.5926 0.0841 0.022 Uiso 1 1 calc R U . . .
C5 C 0.18573(12) 0.25535(12) -0.04235(6) 0.0218(3) Uani 1 1 d . . . . .
H5A H 0.1555 0.2005 -0.0129 0.033 Uiso 1 1 calc R U . . .
H5B H 0.1683 0.2218 -0.0801 0.033 Uiso 1 1 calc R U . . .
H5C H 0.1473 0.3345 -0.0385 0.033 Uiso 1 1 calc R U . . .
C6 C 0.42523(12) 0.13196(12) -0.05581(5) 0.0225(3) Uani 1 1 d . . . . .
H6A H 0.5110 0.1414 -0.0503 0.034 Uiso 1 1 calc R U . . .
H6B H 0.4088 0.1156 -0.0961 0.034 Uiso 1 1 calc R U . . .
H6C H 0.3965 0.0643 -0.0326 0.034 Uiso 1 1 calc R U . . .
C7 C 0.40913(13) 0.40665(12) -0.07161(5) 0.0240(3) Uani 1 1 d . . . . .
H7A H 0.3733 0.4803 -0.0559 0.036 Uiso 1 1 calc R U . . .
H7B H 0.3907 0.4008 -0.1124 0.036 Uiso 1 1 calc R U . . .
H7C H 0.4954 0.4097 -0.0664 0.036 Uiso 1 1 calc R U . . .
C8 C 0.60252(11) 0.10407(11) 0.19320(5) 0.0180(3) Uani 1 1 d . . . . .
H8A H 0.5442 0.0430 0.1817 0.027 Uiso 1 1 calc R U . . .
H8B H 0.6423 0.0779 0.2283 0.027 Uiso 1 1 calc R U . . .
H8C H 0.6615 0.1142 0.1628 0.027 Uiso 1 1 calc R U . . .
C9 C 0.43291(12) 0.24085(11) 0.27099(5) 0.0193(3) Uani 1 1 d . . . . .
H9A H 0.3966 0.3199 0.2784 0.029 Uiso 1 1 calc R U . . .
H9B H 0.4824 0.2176 0.3036 0.029 Uiso 1 1 calc R U . . .
H9C H 0.3704 0.1803 0.2654 0.029 Uiso 1 1 calc R U . . .
C10 C 0.62742(11) 0.38143(11) 0.21043(5) 0.0191(3) Uani 1 1 d . . . . .
H10A H 0.6785 0.3834 0.1766 0.029 Uiso 1 1 calc R U . . .
H10B H 0.6767 0.3744 0.2447 0.029 Uiso 1 1 calc R U . . .
H10C H 0.5807 0.4561 0.2123 0.029 Uiso 1 1 calc R U . . .
N1 N 0.26697(9) 0.45033(9) 0.05525(4) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.33928(9) 0.43540(9) 0.16907(4) 0.0164(2) Uani 1 1 d . . . . .
O1 O 0.38243(7) 0.28313(7) 0.03608(3) 0.01256(18) Uani 1 1 d . . . . .
O2 O 0.44402(7) 0.26301(7) 0.14618(3) 0.01304(17) Uani 1 1 d . . . . .
Si1 Si 0.34851(3) 0.27286(3) -0.03397(2) 0.01234(9) Uani 1 1 d . . . . .
Si2 Si 0.52615(3) 0.24990(3) 0.20598(2) 0.01108(9) 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 1.3124(14) . ?
C1 O1 1.3397(13) . ?
C1 C2 1.4243(15) . ?
C2 N2 1.3115(14) . ?
C2 O2 1.3411(13) . ?
C3 N2 1.3562(15) . ?
C3 C4 1.3629(17) . ?
C3 H3 0.9500 . ?
C4 N1 1.3569(15) . ?
C4 H4 0.9500 . ?
C5 Si1 1.8535(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 Si1 1.8532(13) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 Si1 1.8524(13) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si2 1.8513(12) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 Si2 1.8530(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 Si2 1.8507(12) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1 Si1 1.6892(9) . ?
O2 Si2 1.6852(8) . ?

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 O1 120.62(10) . . ?
N1 C1 C2 121.48(10) . . ?
O1 C1 C2 117.90(10) . . ?
N2 C2 O2 120.61(10) . . ?
N2 C2 C1 121.42(10) . . ?
O2 C2 C1 117.97(10) . . ?
N2 C3 C4 122.21(11) . . ?
N2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
N1 C4 C3 121.43(11) . . ?
N1 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si2 C8 H8A 109.5 . . ?
Si2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si2 C9 H9A 109.5 . . ?
Si2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si2 C10 H10A 109.5 . . ?
Si2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C4 116.85(10) . . ?
C2 N2 C3 116.55(10) . . ?
C1 O1 Si1 125.98(7) . . ?
C2 O2 Si2 127.34(7) . . ?
O1 Si1 C7 109.01(5) . . ?
O1 Si1 C6 102.68(5) . . ?
C7 Si1 C6 111.57(6) . . ?
O1 Si1 C5 109.49(5) . . ?
C7 Si1 C5 113.41(6) . . ?
C6 Si1 C5 110.12(6) . . ?
O2 Si2 C10 108.50(5) . . ?
O2 Si2 C8 101.27(5) . . ?
C10 Si2 C8 114.01(6) . . ?
O2 Si2 C9 112.17(5) . . ?
C10 Si2 C9 110.19(6) . . ?
C8 Si2 C9 110.44(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -2.44(17) . . . . ?
O1 C1 C2 N2 177.69(10) . . . . ?
N1 C1 C2 O2 176.73(10) . . . . ?
O1 C1 C2 O2 -3.15(15) . . . . ?
N2 C3 C4 N1 -1.8(2) . . . . ?
O1 C1 N1 C4 -179.23(10) . . . . ?
C2 C1 N1 C4 0.89(16) . . . . ?
C3 C4 N1 C1 1.10(18) . . . . ?
O2 C2 N2 C3 -177.39(10) . . . . ?
C1 C2 N2 C3 1.76(17) . . . . ?
C4 C3 N2 C2 0.24(19) . . . . ?
N1 C1 O1 Si1 -2.56(15) . . . . ?
C2 C1 O1 Si1 177.32(8) . . . . ?
N2 C2 O2 Si2 -18.05(15) . . . . ?
C1 C2 O2 Si2 162.78(8) . . . . ?
C1 O1 Si1 C7 67.57(10) . . . . ?
C1 O1 Si1 C6 -174.00(9) . . . . ?
C1 O1 Si1 C5 -57.02(10) . . . . ?
C2 O2 Si2 C10 -56.02(10) . . . . ?
C2 O2 Si2 C8 -176.30(9) . . . . ?
C2 O2 Si2 C9 65.95(10) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_fin145_2
_database_code_depnum_ccdc_archive 'CCDC 1484825'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT026_fin145_2            
;
PROBLEM: Ratio Observed / Unique Reflections too Low ....         18 %     
RESPONSE: The crystal was very weakly scattering and a non-merohedral twin
further complicating an appropriate integration. Best refinement results were
reached with merging friedel pairs and equivalent reflections during 
integration instead of an absorption correction. This circumstance equally 
apply to the B-Alerts. 
;
_audit_contact_author            'Joerg Sundermeyer'
_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 H6 B2 F2 Li2 N18 O, 3(C2 H3 N)
;
_chemical_formula_sum            'C14 H15 B2 F2 Li2 N21 O'
_chemical_formula_weight         566.97

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   9.6535(14)
_cell_length_b                   18.036(2)
_cell_length_c                   15.8966(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.860(10)
_cell_angle_gamma                90
_cell_volume                     2708.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2245
_cell_measurement_theta_min      1.72
_cell_measurement_theta_max      23.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            13720
_diffrn_reflns_av_unetI/netI     0.6013
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         25.612
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13720
_reflns_number_gt                2420
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, 
R. Spagna, J. Appl. Cryst. 1999, 32, 115-119)
;

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
Ortep-3 for Windows (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 
102, 53227 Bonn, Germany)
;

_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
ShelXle (C. B. Huebschle, G. M. Sheldrick, B. Dittrich, J. Appl. Cryst. 
2011, 44, 1281-1284)
;
_refine_special_details          'Refined as a 2-component twin., 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)+(0.0096P)²] 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         13720
_refine_ls_number_parameters     385
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.2816
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.589
_refine_ls_restrained_S_all      0.589
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002

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 0.9522(11) 0.1988(6) 0.1973(7) 0.018(3) Uani 1 1 d . U . . .
C2 C 1.0357(10) 0.2035(6) 0.2827(7) 0.022(3) Uani 1 1 d . U . . .
C3 C 0.5853(11) 0.2014(6) 0.3125(7) 0.021(3) Uani 1 1 d . . . . .
C4 C 0.6702(10) 0.1974(6) 0.3968(7) 0.021(3) Uani 1 1 d . . . . .
C5 C 0.8053(14) 0.4424(8) 1.0412(9) 0.080(5) Uani 1 1 d . . . . .
H5A H 0.7252 0.4764 1.0241 0.120 Uiso 1 1 calc R U . . .
H5B H 0.8724 0.4635 1.0901 0.120 Uiso 1 1 calc R U . . .
H5C H 0.7709 0.3946 1.0578 0.120 Uiso 1 1 calc R U . . .
C6 C 0.8774(11) 0.4315(8) 0.9677(9) 0.050(4) Uani 1 1 d . . . . .
C7 C 0.4676(13) 0.1289(6) 0.9667(8) 0.047(3) Uani 1 1 d . . . . .
H7A H 0.4357 0.1401 0.9054 0.071 Uiso 1 1 calc R U . . .
H7B H 0.5565 0.1010 0.9754 0.071 Uiso 1 1 calc R U . . .
H7C H 0.4827 0.1753 0.9994 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3607(13) 0.0849(7) 0.9962(8) 0.049(4) Uani 1 1 d . . . . .
C9 C 0.0835(13) 0.4915(7) 0.2737(9) 0.065(4) Uani 1 1 d . . . . .
H9A H 0.1290 0.4889 0.3347 0.098 Uiso 1 1 calc R U . . .
H9B H -0.0190 0.4855 0.2674 0.098 Uiso 1 1 calc R U . . .
H9C H 0.1036 0.5397 0.2504 0.098 Uiso 1 1 calc R U . . .
C10 C 0.1390(12) 0.4320(7) 0.2264(8) 0.038(3) Uani 1 1 d . . . . .
C11 C 0.5642(11) 0.4058(6) 0.1839(8) 0.045(3) Uani 1 1 d . . . . .
H11A H 0.4896 0.4017 0.2172 0.068 Uiso 1 1 calc R U . . .
H11B H 0.5286 0.3872 0.1255 0.068 Uiso 1 1 calc R U . . .
H11C H 0.5921 0.4578 0.1812 0.068 Uiso 1 1 calc R U . . .
C12 C 0.6871(12) 0.3617(6) 0.2253(7) 0.029(3) Uani 1 1 d . . . . .
C13 C 1.4966(12) 0.5232(5) 0.3775(8) 0.041(3) Uani 1 1 d . . . . .
H13A H 1.4336 0.5576 0.3993 0.061 Uiso 1 1 calc R U . . .
H13B H 1.4868 0.5305 0.3155 0.061 Uiso 1 1 calc R U . . .
H13C H 1.5947 0.5328 0.4065 0.061 Uiso 1 1 calc R U . . .
C14 C 1.4586(12) 0.4466(7) 0.3943(8) 0.033(3) Uani 1 1 d . . . . .
Li1 Li 0.2129(17) 0.2756(11) 0.1617(11) 0.026(5) Uani 1 1 d . . . . .
Li2 Li 1.4158(16) 0.2752(10) 0.4307(10) 0.025(5) Uani 1 1 d . . . . .
B1 B 0.7322(12) 0.1169(7) 0.2181(9) 0.023(3) Uani 1 1 d . . . . .
B2 B 0.8912(13) 0.1198(7) 0.3720(9) 0.021(3) Uani 1 1 d . U . . .
N1 N 0.8238(9) 0.1690(5) 0.1682(6) 0.021(2) Uani 1 1 d . U . . .
N2 N 0.7896(9) 0.1800(6) 0.0827(6) 0.032(3) Uani 1 1 d . . . . .
N3 N 0.8942(9) 0.2156(5) 0.0612(6) 0.026(2) Uani 1 1 d . . . . .
N4 N 0.9990(8) 0.2291(5) 0.1319(6) 0.023(2) Uani 1 1 d . . . . .
N5 N 1.0154(8) 0.1755(5) 0.3570(6) 0.020(2) Uani 1 1 d . U . . .
N6 N 1.1258(9) 0.1967(5) 0.4198(6) 0.028(2) Uani 1 1 d . . . . .
N7 N 1.2076(8) 0.2358(5) 0.3822(6) 0.026(2) Uani 1 1 d . . . . .
N8 N 1.1542(9) 0.2428(5) 0.2962(6) 0.026(2) Uani 1 1 d . . . . .
N9 N 0.4648(8) 0.2407(5) 0.2980(6) 0.023(2) Uani 1 1 d . . . . .
N10 N 0.4123(9) 0.2351(5) 0.2134(6) 0.027(2) Uani 1 1 d . . . . .
N11 N 0.4954(9) 0.1912(5) 0.1765(6) 0.023(2) Uani 1 1 d . . . . .
N12 N 0.6083(8) 0.1703(5) 0.2383(5) 0.017(2) Uani 1 1 d . . . . .
N13 N 0.7983(9) 0.1642(5) 0.4253(6) 0.024(2) Uani 1 1 d . . . . .
N14 N 0.8312(9) 0.1753(5) 0.5115(6) 0.025(2) Uani 1 1 d . . . . .
N15 N 0.7290(9) 0.2136(5) 0.5333(6) 0.028(2) Uani 1 1 d . . . . .
N16 N 0.6266(9) 0.2287(5) 0.4639(6) 0.027(2) Uani 1 1 d . . . . .
N17 N 0.9333(11) 0.4225(5) 0.9119(8) 0.061(3) Uani 1 1 d . . . . .
N18 N 0.2775(12) 0.0481(7) 1.0187(8) 0.077(4) Uani 1 1 d . . . . .
N19 N 0.1790(12) 0.3850(5) 0.1920(7) 0.037(3) Uani 1 1 d . . . . .
N20 N 0.7871(9) 0.3296(5) 0.2587(6) 0.044(3) Uani 1 1 d . . . . .
N21 N 1.4315(10) 0.3862(5) 0.4062(6) 0.036(3) Uani 1 1 d . . . . .
F1 F 0.6682(6) 0.0648(3) 0.1637(4) 0.0302(16) Uani 1 1 d . . . . .
F2 F 0.9584(6) 0.0648(3) 0.4271(4) 0.0272(16) Uani 1 1 d . . . . .
O1 O 0.8133(8) 0.0926(3) 0.2962(5) 0.0225(14) 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 N4 1.334(12) . ?
C1 N1 1.342(13) . ?
C1 C2 1.432(15) . ?
C2 N8 1.325(12) . ?
C2 N5 1.335(12) . ?
C3 N9 1.340(13) . ?
C3 N12 1.365(12) . ?
C3 C4 1.422(15) . ?
C4 N16 1.348(11) . ?
C4 N13 1.364(12) . ?
C5 C6 1.491(16) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N17 1.140(14) . ?
C7 C8 1.454(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N18 1.154(14) . ?
C9 C10 1.473(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N19 1.120(13) . ?
C11 C12 1.467(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N20 1.158(13) . ?
C13 C14 1.468(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N21 1.145(13) . ?
Li1 N10 2.065(19) . ?
Li1 N19 2.07(2) . ?
Li1 N15 2.088(19) 4_565 ?
Li1 N4 2.188(19) 1_455 ?
Li1 N8 2.395(19) 1_455 ?
Li2 N21 2.05(2) . ?
Li2 N7 2.122(19) . ?
Li2 N3 2.133(19) 4_666 ?
Li2 N16 2.164(18) 1_655 ?
Li2 N9 2.339(18) 1_655 ?
B1 F1 1.339(13) . ?
B1 O1 1.394(14) . ?
B1 N1 1.608(14) . ?
B1 N12 1.619(13) . ?
B2 O1 1.373(14) . ?
B2 F2 1.392(13) . ?
B2 N13 1.573(13) . ?
B2 N5 1.619(13) . ?
N1 N2 1.347(12) . ?
N2 N3 1.301(11) . ?
N3 N4 1.371(11) . ?
N3 Li2 2.133(19) 4_565 ?
N4 Li1 2.188(19) 1_655 ?
N5 N6 1.357(11) . ?
N6 N7 1.294(11) . ?
N7 N8 1.364(11) . ?
N8 Li1 2.395(19) 1_655 ?
N9 N10 1.340(11) . ?
N9 Li2 2.339(18) 1_455 ?
N10 N11 1.344(11) . ?
N11 N12 1.362(11) . ?
N13 N14 1.357(11) . ?
N14 N15 1.308(10) . ?
N15 N16 1.350(12) . ?
N15 Li1 2.088(19) 4_666 ?
N16 Li2 2.164(18) 1_455 ?

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
N4 C1 N1 109.4(10) . . ?
N4 C1 C2 120.0(10) . . ?
N1 C1 C2 130.6(10) . . ?
N8 C2 N5 109.8(10) . . ?
N8 C2 C1 119.0(9) . . ?
N5 C2 C1 131.2(10) . . ?
N9 C3 N12 111.0(10) . . ?
N9 C3 C4 120.1(10) . . ?
N12 C3 C4 128.9(10) . . ?
N16 C4 N13 109.3(9) . . ?
N16 C4 C3 120.7(10) . . ?
N13 C4 C3 130.0(9) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N17 C6 C5 179.2(16) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N18 C8 C7 178.0(14) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N19 C10 C9 177.6(13) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N20 C12 C11 177.3(12) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N21 C14 C13 178.2(11) . . ?
N10 Li1 N19 115.1(10) . . ?
N10 Li1 N15 99.8(7) . 4_565 ?
N19 Li1 N15 100.7(8) . 4_565 ?
N10 Li1 N4 135.4(10) . 1_455 ?
N19 Li1 N4 103.2(8) . 1_455 ?
N15 Li1 N4 94.6(8) 4_565 1_455 ?
N10 Li1 N8 86.0(7) . 1_455 ?
N19 Li1 N8 87.2(7) . 1_455 ?
N15 Li1 N8 167.0(10) 4_565 1_455 ?
N4 Li1 N8 73.3(5) 1_455 1_455 ?
N21 Li2 N7 111.0(8) . . ?
N21 Li2 N3 97.7(8) . 4_666 ?
N7 Li2 N3 96.0(7) . 4_666 ?
N21 Li2 N16 108.8(8) . 1_655 ?
N7 Li2 N16 137.1(10) . 1_655 ?
N3 Li2 N16 93.9(7) 4_666 1_655 ?
N21 Li2 N9 93.0(7) . 1_655 ?
N7 Li2 N9 86.2(7) . 1_655 ?
N3 Li2 N9 167.4(9) 4_666 1_655 ?
N16 Li2 N9 76.2(6) 1_655 1_655 ?
F1 B1 O1 117.1(10) . . ?
F1 B1 N1 108.6(9) . . ?
O1 B1 N1 110.9(9) . . ?
F1 B1 N12 106.5(8) . . ?
O1 B1 N12 108.2(9) . . ?
N1 B1 N12 104.7(8) . . ?
O1 B2 F2 113.5(9) . . ?
O1 B2 N13 112.6(9) . . ?
F2 B2 N13 105.5(9) . . ?
O1 B2 N5 112.4(9) . . ?
F2 B2 N5 105.7(9) . . ?
N13 B2 N5 106.5(8) . . ?
C1 N1 N2 107.9(8) . . ?
C1 N1 B1 128.8(10) . . ?
N2 N1 B1 122.5(9) . . ?
N3 N2 N1 107.1(8) . . ?
N2 N3 N4 110.7(9) . . ?
N2 N3 Li2 122.0(8) . 4_565 ?
N4 N3 Li2 125.5(7) . 4_565 ?
C1 N4 N3 104.8(8) . . ?
C1 N4 Li1 116.4(9) . 1_655 ?
N3 N4 Li1 138.6(8) . 1_655 ?
C2 N5 N6 107.9(8) . . ?
C2 N5 B2 127.8(9) . . ?
N6 N5 B2 124.0(9) . . ?
N7 N6 N5 106.0(8) . . ?
N6 N7 N8 111.9(8) . . ?
N6 N7 Li2 129.5(9) . . ?
N8 N7 Li2 117.9(8) . . ?
C2 N8 N7 104.4(8) . . ?
C2 N8 Li1 110.0(9) . 1_655 ?
N7 N8 Li1 143.8(7) . 1_655 ?
N10 N9 C3 105.6(8) . . ?
N10 N9 Li2 145.2(7) . 1_455 ?
C3 N9 Li2 108.3(8) . 1_455 ?
N9 N10 N11 110.3(9) . . ?
N9 N10 Li1 120.1(8) . . ?
N11 N10 Li1 128.7(9) . . ?
N10 N11 N12 108.0(8) . . ?
N11 N12 C3 105.2(8) . . ?
N11 N12 B1 122.4(8) . . ?
C3 N12 B1 132.4(10) . . ?
N14 N13 C4 106.2(8) . . ?
N14 N13 B2 125.3(9) . . ?
C4 N13 B2 128.5(9) . . ?
N15 N14 N13 108.2(8) . . ?
N14 N15 N16 110.8(8) . . ?
N14 N15 Li1 121.4(9) . 4_666 ?
N16 N15 Li1 126.3(8) . 4_666 ?
C4 N16 N15 105.5(8) . . ?
C4 N16 Li2 113.6(9) . 1_455 ?
N15 N16 Li2 140.5(8) . 1_455 ?
C10 N19 Li1 157.0(11) . . ?
C14 N21 Li2 171.2(11) . . ?
B2 O1 B1 140.8(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
N4 C1 C2 N8 4.8(16) . . . . ?
N1 C1 C2 N8 -173.1(10) . . . . ?
N4 C1 C2 N5 -176.7(10) . . . . ?
N1 C1 C2 N5 5(2) . . . . ?
N9 C3 C4 N16 4.2(16) . . . . ?
N12 C3 C4 N16 -176.5(10) . . . . ?
N9 C3 C4 N13 -176.4(10) . . . . ?
N12 C3 C4 N13 2.9(19) . . . . ?
N4 C1 N1 N2 0.7(12) . . . . ?
C2 C1 N1 N2 178.8(11) . . . . ?
N4 C1 N1 B1 170.8(9) . . . . ?
C2 C1 N1 B1 -11.1(18) . . . . ?
F1 B1 N1 C1 -141.0(10) . . . . ?
O1 B1 N1 C1 -11.0(15) . . . . ?
N12 B1 N1 C1 105.5(11) . . . . ?
F1 B1 N1 N2 27.8(13) . . . . ?
O1 B1 N1 N2 157.8(9) . . . . ?
N12 B1 N1 N2 -85.7(11) . . . . ?
C1 N1 N2 N3 -0.3(12) . . . . ?
B1 N1 N2 N3 -171.1(9) . . . . ?
N1 N2 N3 N4 -0.2(12) . . . . ?
N1 N2 N3 Li2 165.5(9) . . . 4_565 ?
N1 C1 N4 N3 -0.8(11) . . . . ?
C2 C1 N4 N3 -179.1(9) . . . . ?
N1 C1 N4 Li1 -176.4(8) . . . 1_655 ?
C2 C1 N4 Li1 5.3(13) . . . 1_655 ?
N2 N3 N4 C1 0.6(11) . . . . ?
Li2 N3 N4 C1 -164.4(9) 4_565 . . . ?
N2 N3 N4 Li1 174.6(11) . . . 1_655 ?
Li2 N3 N4 Li1 9.6(16) 4_565 . . 1_655 ?
N8 C2 N5 N6 -1.0(12) . . . . ?
C1 C2 N5 N6 -179.5(11) . . . . ?
N8 C2 N5 B2 -175.8(9) . . . . ?
C1 C2 N5 B2 5.7(19) . . . . ?
O1 B2 N5 C2 9.4(15) . . . . ?
F2 B2 N5 C2 133.7(10) . . . . ?
N13 B2 N5 C2 -114.3(11) . . . . ?
O1 B2 N5 N6 -164.6(9) . . . . ?
F2 B2 N5 N6 -40.3(13) . . . . ?
N13 B2 N5 N6 71.6(12) . . . . ?
C2 N5 N6 N7 -0.1(11) . . . . ?
B2 N5 N6 N7 174.9(9) . . . . ?
N5 N6 N7 N8 1.2(12) . . . . ?
N5 N6 N7 Li2 -169.5(9) . . . . ?
N5 C2 N8 N7 1.6(12) . . . . ?
C1 C2 N8 N7 -179.7(9) . . . . ?
N5 C2 N8 Li1 170.2(8) . . . 1_655 ?
C1 C2 N8 Li1 -11.0(13) . . . 1_655 ?
N6 N7 N8 C2 -1.7(12) . . . . ?
Li2 N7 N8 C2 170.1(9) . . . . ?
N6 N7 N8 Li1 -163.5(12) . . . 1_655 ?
Li2 N7 N8 Li1 8(2) . . . 1_655 ?
N12 C3 N9 N10 -0.9(12) . . . . ?
C4 C3 N9 N10 178.5(10) . . . . ?
N12 C3 N9 Li2 170.9(8) . . . 1_455 ?
C4 C3 N9 Li2 -9.7(13) . . . 1_455 ?
C3 N9 N10 N11 2.2(11) . . . . ?
Li2 N9 N10 N11 -164.1(12) 1_455 . . . ?
C3 N9 N10 Li1 172.2(9) . . . . ?
Li2 N9 N10 Li1 6(2) 1_455 . . . ?
N9 N10 N11 N12 -2.7(11) . . . . ?
Li1 N10 N11 N12 -171.6(9) . . . . ?
N10 N11 N12 C3 2.0(10) . . . . ?
N10 N11 N12 B1 180.0(8) . . . . ?
N9 C3 N12 N11 -0.7(12) . . . . ?
C4 C3 N12 N11 180.0(10) . . . . ?
N9 C3 N12 B1 -178.4(10) . . . . ?
C4 C3 N12 B1 2.3(19) . . . . ?
F1 B1 N12 N11 -40.1(13) . . . . ?
O1 B1 N12 N11 -166.8(8) . . . . ?
N1 B1 N12 N11 74.8(11) . . . . ?
F1 B1 N12 C3 137.2(11) . . . . ?
O1 B1 N12 C3 10.6(16) . . . . ?
N1 B1 N12 C3 -107.8(13) . . . . ?
N16 C4 N13 N14 0.7(11) . . . . ?
C3 C4 N13 N14 -178.6(11) . . . . ?
N16 C4 N13 B2 179.2(9) . . . . ?
C3 C4 N13 B2 -0.1(18) . . . . ?
O1 B2 N13 N14 156.2(9) . . . . ?
F2 B2 N13 N14 31.9(13) . . . . ?
N5 B2 N13 N14 -80.2(12) . . . . ?
O1 B2 N13 C4 -22.0(15) . . . . ?
F2 B2 N13 C4 -146.4(10) . . . . ?
N5 B2 N13 C4 101.6(12) . . . . ?
C4 N13 N14 N15 -0.6(11) . . . . ?
B2 N13 N14 N15 -179.2(9) . . . . ?
N13 N14 N15 N16 0.2(12) . . . . ?
N13 N14 N15 Li1 166.8(8) . . . 4_666 ?
N13 C4 N16 N15 -0.6(12) . . . . ?
C3 C4 N16 N15 178.9(10) . . . . ?
N13 C4 N16 Li2 -174.8(8) . . . 1_455 ?
C3 C4 N16 Li2 4.6(14) . . . 1_455 ?
N14 N15 N16 C4 0.2(12) . . . . ?
Li1 N15 N16 C4 -165.5(9) 4_666 . . . ?
N14 N15 N16 Li2 171.9(11) . . . 1_455 ?
Li1 N15 N16 Li2 6.2(18) 4_666 . . 1_455 ?
F2 B2 O1 B1 -176.2(10) . . . . ?
N13 B2 O1 B1 63.9(16) . . . . ?
N5 B2 O1 B1 -56.4(17) . . . . ?
F1 B1 O1 B2 -176.3(10) . . . . ?
N1 B1 O1 B2 58.3(16) . . . . ?
N12 B1 O1 B2 -56.1(17) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.073

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_FIN085
_database_code_depnum_ccdc_archive 'CCDC 1484826'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;

# start Validation Reply Form  
_vrf_PLAT430_FIN085              
;
PROBLEM: Short Inter D...A Contact  O3     ..  O4      ..       2.80 Ang.
RESPONSE: There is a short intermolecular Distance, but no hydrogen atom 
in between. Denotation as Donor and Acceptor is in this case inappropriate.
;
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
3(C12 B N8 O4), 3(C6 H11 N2), 2(C2 H3 N)
;
_chemical_formula_sum            'C58 H39 B3 N32 O12'
_chemical_formula_weight         1408.64

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   15.460(5)
_cell_length_b                   9.897(5)
_cell_length_c                   41.241(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.289(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     6300(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    121
_cell_measurement_theta_min      3.5077
_cell_measurement_theta_max      24.0477

_exptl_crystal_description       plate
_exptl_crystal_colour            'fluorescent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             2888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5733
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            54995
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         27.161
_diffrn_reflns_theta_full        25.000
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6977
_reflns_number_gt                4187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v3.0.28'
_computing_cell_refinement       'APEX2 v2013.4-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, 
R. Spagna, J. Appl. Cryst. 1999, 32, 115-119)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
Ortep-3 for Windows (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 
102, 53227 Bonn, Germany)
;

_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
ShelXle (C. B. Huebschle, G. M. Sheldrick, B. Dittrich, J. Appl. Cryst. 
2011, 44, 1281-1284)
;
_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)+(0.0515P)²+13.3756P] 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         6977
_refine_ls_number_parameters     516
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24142(18) 0.1812(3) 0.67440(6) 0.0291(7) Uani 1 1 d . . . . .
C2 C 0.15676(18) 0.2313(3) 0.67944(6) 0.0268(6) Uani 1 1 d . . . . .
C3 C 0.20875(16) 0.1822(3) 0.62121(6) 0.0232(6) Uani 1 1 d . . . . .
C4 C 0.12697(16) 0.2271(3) 0.62628(6) 0.0219(6) Uani 1 1 d . . . . .
C5 C 0.23456(16) 0.1583(3) 0.58875(7) 0.0258(6) Uani 1 1 d . . . . .
C6 C 0.06617(17) 0.2467(3) 0.59903(6) 0.0253(6) Uani 1 1 d . . . . .
C7 C 0.28250(19) 0.2831(3) 0.77719(6) 0.0293(7) Uani 1 1 d . . . . .
C8 C 0.25046(19) 0.1492(3) 0.78078(6) 0.0296(7) Uani 1 1 d . . . . .
C9 C 0.32451(16) 0.2834(3) 0.82947(6) 0.0219(6) Uani 1 1 d . . . . .
C10 C 0.29428(16) 0.1539(3) 0.83257(6) 0.0219(6) Uani 1 1 d . . . . .
C11 C 0.36677(16) 0.3524(3) 0.85663(6) 0.0234(6) Uani 1 1 d . . . . .
C12 C 0.30592(16) 0.0844(3) 0.86330(6) 0.0225(6) Uani 1 1 d . . . . .
C13 C 0.49813(15) 0.0042(3) 0.69671(6) 0.0200(6) Uani 1 1 d . . . . .
C14 C 0.43698(16) -0.1001(3) 0.70062(6) 0.0208(6) Uani 1 1 d . . . . .
C15 C 0.46063(15) 0.0099(2) 0.64407(6) 0.0194(5) Uani 1 1 d . . . . .
C16 C 0.40339(15) -0.0945(2) 0.64768(6) 0.0195(5) Uani 1 1 d . . . . .
C17 C 0.46859(16) 0.0719(3) 0.61272(6) 0.0235(6) Uani 1 1 d . . . . .
C18 C 0.35311(16) -0.1464(3) 0.61998(6) 0.0223(6) Uani 1 1 d . . . . .
C41 C 0.8862(2) 0.9551(3) 0.59254(8) 0.0463(8) Uani 1 1 d . . . . .
H25A H 0.8878 1.0435 0.6033 0.069 Uiso 1 1 calc R U . . .
H25B H 0.9452 0.9192 0.5921 0.069 Uiso 1 1 calc R U . . .
H25C H 0.8504 0.8929 0.6045 0.069 Uiso 1 1 calc R U . . .
C42 C 0.8494(2) 0.9697(3) 0.55951(10) 0.0456(8) Uani 1 1 d . . . . .
B1 B 0.2286(3) 0.2110(3) 0.72855(8) 0.0387(9) Uani 1 1 d . . . . .
B2 B 0.5000 -0.0518(4) 0.7500 0.0237(9) Uani 1 2 d S T P . .
N1 N 0.27035(14) 0.1575(2) 0.64592(5) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.09777(14) 0.2540(2) 0.65634(5) 0.0251(5) Uani 1 1 d . . . . .
N3 N 0.25361(15) 0.1418(3) 0.56266(6) 0.0373(6) Uani 1 1 d . . . . .
N4 N 0.01867(15) 0.2605(3) 0.57682(6) 0.0376(6) Uani 1 1 d . . . . .
N5 N 0.25493(14) 0.0810(2) 0.80768(5) 0.0262(5) Uani 1 1 d . . . . .
N6 N 0.31950(14) 0.3536(2) 0.80076(5) 0.0268(5) Uani 1 1 d . . . . .
N7 N 0.40135(15) 0.4076(2) 0.87815(6) 0.0323(6) Uani 1 1 d . . . . .
N8 N 0.31584(14) 0.0289(2) 0.88752(5) 0.0291(5) Uani 1 1 d . . . . .
N9 N 0.38893(13) -0.1526(2) 0.67694(5) 0.0218(5) Uani 1 1 d . . . . .
N10 N 0.51104(13) 0.0631(2) 0.66929(5) 0.0205(5) Uani 1 1 d . . . . .
N11 N 0.47354(15) 0.1211(2) 0.58774(5) 0.0316(6) Uani 1 1 d . . . . .
N12 N 0.31386(14) -0.1883(2) 0.59787(6) 0.0323(6) Uani 1 1 d . . . . .
N41 N 0.8209(2) 0.9803(3) 0.53372(8) 0.0626(9) Uani 1 1 d . . . . .
O1 O 0.28584(13) 0.1648(2) 0.70249(4) 0.0382(5) Uani 1 1 d . . . . .
O2 O 0.14643(13) 0.24985(19) 0.71073(4) 0.0352(5) Uani 1 1 d . . . . .
O3 O 0.27047(15) 0.32313(19) 0.74669(4) 0.0402(6) Uani 1 1 d . . . . .
O4 O 0.21478(15) 0.10515(19) 0.75266(4) 0.0413(6) Uani 1 1 d . . . . .
O5 O 0.43520(11) -0.13598(18) 0.73158(4) 0.0262(4) Uani 1 1 d . . . . .
O6 O 0.53863(11) 0.03489(18) 0.72513(4) 0.0243(4) Uani 1 1 d . . . . .
C27 C 0.4318(2) -0.4062(4) 0.46288(8) 0.0525(9) Uani 1 1 d . . . . .
H23A H 0.4268 -0.4409 0.4850 0.079 Uiso 1 1 calc R U . . .
H23B H 0.4885 -0.3633 0.4613 0.079 Uiso 1 1 calc R U . . .
H23C H 0.4260 -0.4811 0.4473 0.079 Uiso 1 1 calc R U . . .
C22 C 0.37473(19) -0.0631(3) 0.46875(7) 0.0393(8) Uani 1 1 d D . . . .
H19 H 0.3762 -0.0317 0.4470 0.047 Uiso 1 1 calc R U . . .
C24 C 0.37383(19) -0.0678(3) 0.52107(6) 0.0361(7) Uani 1 1 d D . . . .
H20 H 0.3743 -0.0392 0.5431 0.043 Uiso 1 1 calc R U . . .
C25 C 0.3685(2) -0.1954(3) 0.51067(7) 0.0402(8) Uani 1 1 d D . . . .
H21 H 0.3652 -0.2741 0.5237 0.048 Uiso 1 1 calc R U . . .
C26 C 0.3636(2) -0.3072(4) 0.45554(8) 0.0525(10) Uani 1 1 d D . . . .
H22A H 0.3066 -0.3515 0.4570 0.063 Uiso 1 1 calc R U . . .
H22B H 0.3677 -0.2752 0.4329 0.063 Uiso 1 1 calc R U . . .
C28 C 0.3825(2) 0.1644(3) 0.49563(8) 0.0505(9) Uani 1 1 d D . . . .
H24A H 0.3286 0.2017 0.4857 0.076 Uiso 1 1 calc R U . . .
H24B H 0.4315 0.1953 0.4835 0.076 Uiso 1 1 calc R U . . .
H24C H 0.3900 0.1950 0.5182 0.076 Uiso 1 1 calc R U . . .
N21 N 0.36871(15) -0.1908(3) 0.47751(5) 0.0352(6) Uani 1 1 d D . . . .
N23 N 0.37843(15) 0.0143(3) 0.49482(5) 0.0341(6) Uani 1 1 d D . . . .
C37 C -0.0723(6) -0.0960(10) 0.6787(2) 0.073(2) Uani 0.5 1 d . U P A -1
H37A H -0.0429 -0.1833 0.6816 0.110 Uiso 0.5 1 calc R U P A -1
H37B H -0.0691 -0.0660 0.6562 0.110 Uiso 0.5 1 calc R U P A -1
H37C H -0.1331 -0.1055 0.6838 0.110 Uiso 0.5 1 calc R U P A -1
C32 C 0.0140(7) 0.0454(8) 0.76121(17) 0.087(3) Uani 0.5 1 d D U P A -1
H32 H 0.0153 0.1414 0.7612 0.104 Uiso 0.5 1 calc R U P A -1
C34 C 0.0142(7) -0.1598(8) 0.77683(19) 0.075(3) Uani 0.5 1 d D U P A -1
H34 H 0.0137 -0.2400 0.7895 0.090 Uiso 0.5 1 calc R U P A -1
C35 C -0.0131(9) -0.1601(7) 0.7440(2) 0.083(3) Uani 0.5 1 d D U P A -1
H35 H -0.0303 -0.2327 0.7300 0.099 Uiso 0.5 1 calc R U P A -1
C36 C -0.0233(5) 0.0197(11) 0.7040(2) 0.063(2) Uani 0.5 1 d D U P A -1
H36A H 0.0329 0.0463 0.6956 0.075 Uiso 0.5 1 calc R U P A -1
H36B H -0.0600 0.1015 0.7047 0.075 Uiso 0.5 1 calc R U P A -1
C38 C 0.0520(7) 0.0044(9) 0.8183(2) 0.075(3) Uani 0.5 1 d D U P A -1
H38A H 0.0067 -0.0239 0.8325 0.113 Uiso 0.5 1 calc R U P A -1
H38B H 0.0505 0.1028 0.8158 0.113 Uiso 0.5 1 calc R U P A -1
H38C H 0.1087 -0.0231 0.8279 0.113 Uiso 0.5 1 calc R U P A -1
N31 N -0.0083(4) -0.0385(6) 0.73860(14) 0.0529(15) Uani 0.5 1 d D U P A -1
N33 N 0.0380(4) -0.0560(7) 0.78819(15) 0.0547(16) Uani 0.5 1 d D U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.302(3) . ?
C1 O1 1.322(3) . ?
C1 C2 1.426(4) . ?
C2 N2 1.300(3) . ?
C2 O2 1.322(3) . ?
C3 C4 1.368(3) . ?
C3 N1 1.376(3) . ?
C3 C5 1.438(4) . ?
C4 N2 1.370(3) . ?
C4 C6 1.436(4) . ?
C5 N3 1.143(3) . ?
C6 N4 1.149(3) . ?
C7 N6 1.302(3) . ?
C7 O3 1.322(3) . ?
C7 C8 1.425(4) . ?
C8 N5 1.297(3) . ?
C8 O4 1.329(3) . ?
C9 N6 1.371(3) . ?
C9 C10 1.372(4) . ?
C9 C11 1.437(4) . ?
C10 N5 1.369(3) . ?
C10 C12 1.444(4) . ?
C11 N7 1.148(3) . ?
C12 N8 1.142(3) . ?
C13 N10 1.298(3) . ?
C13 O6 1.332(3) . ?
C13 C14 1.415(4) . ?
C14 N9 1.301(3) . ?
C14 O5 1.327(3) . ?
C15 N10 1.369(3) . ?
C15 C16 1.374(3) . ?
C15 C17 1.443(4) . ?
C16 N9 1.367(3) . ?
C16 C18 1.439(4) . ?
C17 N11 1.146(3) . ?
C18 N12 1.144(3) . ?
C41 C42 1.453(5) . ?
C41 H25A 0.9800 . ?
C41 H25B 0.9800 . ?
C41 H25C 0.9800 . ?
C42 N41 1.133(4) . ?
B1 O3 1.468(4) . ?
B1 O4 1.468(4) . ?
B1 O2 1.481(4) . ?
B1 O1 1.502(4) . ?
B2 O5 1.479(3) . ?
B2 O5 1.479(3) 2_656 ?
B2 O6 1.488(3) 2_656 ?
B2 O6 1.488(3) . ?
C27 C26 1.458(5) . ?
C27 H23A 0.9800 . ?
C27 H23B 0.9800 . ?
C27 H23C 0.9800 . ?
C22 N23 1.319(4) . ?
C22 N21 1.319(4) . ?
C22 H19 0.9500 . ?
C24 C25 1.335(4) . ?
C24 N23 1.359(3) . ?
C24 H20 0.9500 . ?
C25 N21 1.369(3) . ?
C25 H21 0.9500 . ?
C26 N21 1.465(4) . ?
C26 H22A 0.9900 . ?
C26 H22B 0.9900 . ?
C28 N23 1.487(4) . ?
C28 H24A 0.9800 . ?
C28 H24B 0.9800 . ?
C28 H24C 0.9800 . ?
C37 C36 1.698(14) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C32 N31 1.281(7) . ?
C32 N33 1.528(9) . ?
C32 H32 0.9500 . ?
C34 N33 1.180(8) . ?
C34 C35 1.394(11) . ?
C34 H34 0.9500 . ?
C35 N31 1.227(8) . ?
C35 H35 0.9500 . ?
C36 N31 1.544(9) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C38 N33 1.385(9) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 O1 125.5(3) . . ?
N1 C1 C2 124.0(2) . . ?
O1 C1 C2 110.5(2) . . ?
N2 C2 O2 124.9(2) . . ?
N2 C2 C1 124.4(2) . . ?
O2 C2 C1 110.7(2) . . ?
C4 C3 N1 123.5(2) . . ?
C4 C3 C5 120.3(2) . . ?
N1 C3 C5 116.3(2) . . ?
C3 C4 N2 123.8(2) . . ?
C3 C4 C6 119.6(2) . . ?
N2 C4 C6 116.6(2) . . ?
N3 C5 C3 178.2(3) . . ?
N4 C6 C4 178.4(3) . . ?
N6 C7 O3 125.5(3) . . ?
N6 C7 C8 124.2(2) . . ?
O3 C7 C8 110.3(2) . . ?
N5 C8 O4 125.0(3) . . ?
N5 C8 C7 124.8(2) . . ?
O4 C8 C7 110.1(2) . . ?
N6 C9 C10 123.5(2) . . ?
N6 C9 C11 115.6(2) . . ?
C10 C9 C11 120.9(2) . . ?
N5 C10 C9 124.2(2) . . ?
N5 C10 C12 115.7(2) . . ?
C9 C10 C12 120.0(2) . . ?
N7 C11 C9 179.3(3) . . ?
N8 C12 C10 179.4(3) . . ?
N10 C13 O6 125.2(2) . . ?
N10 C13 C14 124.3(2) . . ?
O6 C13 C14 110.5(2) . . ?
N9 C14 O5 124.9(2) . . ?
N9 C14 C13 124.2(2) . . ?
O5 C14 C13 110.8(2) . . ?
N10 C15 C16 123.3(2) . . ?
N10 C15 C17 116.3(2) . . ?
C16 C15 C17 120.4(2) . . ?
N9 C16 C15 123.5(2) . . ?
N9 C16 C18 116.2(2) . . ?
C15 C16 C18 120.3(2) . . ?
N11 C17 C15 178.9(3) . . ?
N12 C18 C16 179.3(3) . . ?
C42 C41 H25A 109.5 . . ?
C42 C41 H25B 109.5 . . ?
H25A C41 H25B 109.5 . . ?
C42 C41 H25C 109.5 . . ?
H25A C41 H25C 109.5 . . ?
H25B C41 H25C 109.5 . . ?
N41 C42 C41 179.6(4) . . ?
O3 B1 O4 105.8(2) . . ?
O3 B1 O2 113.4(2) . . ?
O4 B1 O2 111.6(3) . . ?
O3 B1 O1 109.5(3) . . ?
O4 B1 O1 112.5(2) . . ?
O2 B1 O1 104.3(2) . . ?
O5 B2 O5 111.4(3) . 2_656 ?
O5 B2 O6 113.07(10) . 2_656 ?
O5 B2 O6 104.92(9) 2_656 2_656 ?
O5 B2 O6 104.92(9) . . ?
O5 B2 O6 113.07(10) 2_656 . ?
O6 B2 O6 109.6(3) 2_656 . ?
C1 N1 C3 112.2(2) . . ?
C2 N2 C4 112.1(2) . . ?
C8 N5 C10 111.5(2) . . ?
C7 N6 C9 111.9(2) . . ?
C14 N9 C16 112.3(2) . . ?
C13 N10 C15 112.3(2) . . ?
C1 O1 B1 107.0(2) . . ?
C2 O2 B1 107.5(2) . . ?
C7 O3 B1 107.0(2) . . ?
C8 O4 B1 106.7(2) . . ?
C14 O5 B2 107.00(18) . . ?
C13 O6 B2 106.74(17) . . ?
C26 C27 H23A 109.5 . . ?
C26 C27 H23B 109.5 . . ?
H23A C27 H23B 109.5 . . ?
C26 C27 H23C 109.5 . . ?
H23A C27 H23C 109.5 . . ?
H23B C27 H23C 109.5 . . ?
N23 C22 N21 109.5(3) . . ?
N23 C22 H19 125.3 . . ?
N21 C22 H19 125.3 . . ?
C25 C24 N23 108.3(3) . . ?
C25 C24 H20 125.8 . . ?
N23 C24 H20 125.8 . . ?
C24 C25 N21 106.6(3) . . ?
C24 C25 H21 126.7 . . ?
N21 C25 H21 126.7 . . ?
C27 C26 N21 112.8(3) . . ?
C27 C26 H22A 109.0 . . ?
N21 C26 H22A 109.0 . . ?
C27 C26 H22B 109.0 . . ?
N21 C26 H22B 109.0 . . ?
H22A C26 H22B 107.8 . . ?
N23 C28 H24A 109.5 . . ?
N23 C28 H24B 109.5 . . ?
H24A C28 H24B 109.5 . . ?
N23 C28 H24C 109.5 . . ?
H24A C28 H24C 109.5 . . ?
H24B C28 H24C 109.5 . . ?
C22 N21 C25 108.0(3) . . ?
C22 N21 C26 125.9(3) . . ?
C25 N21 C26 126.1(3) . . ?
C22 N23 C24 107.5(3) . . ?
C22 N23 C28 126.8(3) . . ?
C24 N23 C28 125.7(2) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N31 C32 N33 98.5(6) . . ?
N31 C32 H32 130.7 . . ?
N33 C32 H32 130.7 . . ?
N33 C34 C35 117.2(8) . . ?
N33 C34 H34 121.4 . . ?
C35 C34 H34 121.4 . . ?
N31 C35 C34 99.0(7) . . ?
N31 C35 H35 130.5 . . ?
C34 C35 H35 130.5 . . ?
N31 C36 C37 110.7(7) . . ?
N31 C36 H36A 109.5 . . ?
C37 C36 H36A 109.5 . . ?
N31 C36 H36B 109.5 . . ?
C37 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
N33 C38 H38A 109.5 . . ?
N33 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N33 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 N31 C32 121.3(7) . . ?
C35 N31 C36 121.8(7) . . ?
C32 N31 C36 116.8(6) . . ?
C34 N33 C38 139.6(8) . . ?
C34 N33 C32 103.1(7) . . ?
C38 N33 C32 112.9(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
N1 C1 C2 N2 2.8(5) . . . . ?
O1 C1 C2 N2 -178.2(3) . . . . ?
N1 C1 C2 O2 -177.9(3) . . . . ?
O1 C1 C2 O2 1.1(3) . . . . ?
N1 C3 C4 N2 0.8(4) . . . . ?
C5 C3 C4 N2 -179.1(2) . . . . ?
N1 C3 C4 C6 -178.3(2) . . . . ?
C5 C3 C4 C6 1.8(4) . . . . ?
N6 C7 C8 N5 -0.8(5) . . . . ?
O3 C7 C8 N5 178.2(3) . . . . ?
N6 C7 C8 O4 178.7(3) . . . . ?
O3 C7 C8 O4 -2.3(3) . . . . ?
N6 C9 C10 N5 -0.8(4) . . . . ?
C11 C9 C10 N5 -178.7(2) . . . . ?
N6 C9 C10 C12 176.9(2) . . . . ?
C11 C9 C10 C12 -1.0(4) . . . . ?
N10 C13 C14 N9 2.8(4) . . . . ?
O6 C13 C14 N9 -178.7(2) . . . . ?
N10 C13 C14 O5 -176.9(2) . . . . ?
O6 C13 C14 O5 1.6(3) . . . . ?
N10 C15 C16 N9 2.2(4) . . . . ?
C17 C15 C16 N9 -176.1(2) . . . . ?
N10 C15 C16 C18 -179.3(2) . . . . ?
C17 C15 C16 C18 2.3(4) . . . . ?
O1 C1 N1 C3 179.2(3) . . . . ?
C2 C1 N1 C3 -2.0(4) . . . . ?
C4 C3 N1 C1 0.3(4) . . . . ?
C5 C3 N1 C1 -179.7(2) . . . . ?
O2 C2 N2 C4 179.3(3) . . . . ?
C1 C2 N2 C4 -1.4(4) . . . . ?
C3 C4 N2 C2 -0.2(4) . . . . ?
C6 C4 N2 C2 178.9(2) . . . . ?
O4 C8 N5 C10 -179.2(3) . . . . ?
C7 C8 N5 C10 0.3(4) . . . . ?
C9 C10 N5 C8 0.5(4) . . . . ?
C12 C10 N5 C8 -177.3(2) . . . . ?
O3 C7 N6 C9 -178.4(3) . . . . ?
C8 C7 N6 C9 0.4(4) . . . . ?
C10 C9 N6 C7 0.3(4) . . . . ?
C11 C9 N6 C7 178.3(2) . . . . ?
O5 C14 N9 C16 178.9(2) . . . . ?
C13 C14 N9 C16 -0.8(3) . . . . ?
C15 C16 N9 C14 -1.6(3) . . . . ?
C18 C16 N9 C14 179.9(2) . . . . ?
O6 C13 N10 C15 179.6(2) . . . . ?
C14 C13 N10 C15 -2.1(3) . . . . ?
C16 C15 N10 C13 -0.3(3) . . . . ?
C17 C15 N10 C13 178.1(2) . . . . ?
N1 C1 O1 B1 177.1(3) . . . . ?
C2 C1 O1 B1 -1.8(3) . . . . ?
O3 B1 O1 C1 -119.8(2) . . . . ?
O4 B1 O1 C1 122.9(3) . . . . ?
O2 B1 O1 C1 1.9(3) . . . . ?
N2 C2 O2 B1 179.5(3) . . . . ?
C1 C2 O2 B1 0.2(3) . . . . ?
O3 B1 O2 C2 117.8(3) . . . . ?
O4 B1 O2 C2 -122.9(3) . . . . ?
O1 B1 O2 C2 -1.2(3) . . . . ?
N6 C7 O3 B1 178.7(3) . . . . ?
C8 C7 O3 B1 -0.3(3) . . . . ?
O4 B1 O3 C7 2.5(3) . . . . ?
O2 B1 O3 C7 125.0(3) . . . . ?
O1 B1 O3 C7 -118.9(2) . . . . ?
N5 C8 O4 B1 -176.7(3) . . . . ?
C7 C8 O4 B1 3.8(3) . . . . ?
O3 B1 O4 C8 -3.9(3) . . . . ?
O2 B1 O4 C8 -127.6(2) . . . . ?
O1 B1 O4 C8 115.6(3) . . . . ?
N9 C14 O5 B2 179.7(2) . . . . ?
C13 C14 O5 B2 -0.6(3) . . . . ?
O5 B2 O5 C14 -123.19(18) 2_656 . . . ?
O6 B2 O5 C14 118.9(2) 2_656 . . . ?
O6 B2 O5 C14 -0.5(3) . . . . ?
N10 C13 O6 B2 176.7(2) . . . . ?
C14 C13 O6 B2 -1.9(3) . . . . ?
O5 B2 O6 C13 1.5(3) . . . . ?
O5 B2 O6 C13 123.1(2) 2_656 . . . ?
O6 B2 O6 C13 -120.25(17) 2_656 . . . ?
N23 C24 C25 N21 -0.8(3) . . . . ?
N23 C22 N21 C25 0.0(3) . . . . ?
N23 C22 N21 C26 -179.7(3) . . . . ?
C24 C25 N21 C22 0.5(3) . . . . ?
C24 C25 N21 C26 -179.8(3) . . . . ?
C27 C26 N21 C22 123.5(4) . . . . ?
C27 C26 N21 C25 -56.2(4) . . . . ?
N21 C22 N23 C24 -0.5(3) . . . . ?
N21 C22 N23 C28 -177.8(3) . . . . ?
C25 C24 N23 C22 0.8(3) . . . . ?
C25 C24 N23 C28 178.1(3) . . . . ?
N33 C34 C35 N31 -5.2(10) . . . . ?
C34 C35 N31 C32 -2.3(12) . . . . ?
C34 C35 N31 C36 174.0(7) . . . . ?
N33 C32 N31 C35 6.8(12) . . . . ?
N33 C32 N31 C36 -169.7(6) . . . . ?
C37 C36 N31 C35 15.5(12) . . . . ?
C37 C36 N31 C32 -168.1(7) . . . . ?
C35 C34 N33 C38 161.6(12) . . . . ?
C35 C34 N33 C32 8.8(9) . . . . ?
N31 C32 N33 C34 -8.7(9) . . . . ?
N31 C32 N33 C38 -170.0(7) . . . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.059

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'acetonitrile. diethyl ether'
_chemical_properties_physical    ', Moisture-sensitive,Hygroscopic'
####################################################################### 
# 
# 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_LHF71
_database_code_depnum_ccdc_archive 'CCDC 1484823'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
2,2'-Bis-(trimethylsilyl)-5,5'-bistetrazol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H18 N8 Si2'
_chemical_formula_sum            'C8 H18 N8 Si2'
_chemical_formula_weight         282.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   7.113(7)
_cell_length_b                   11.2141(13)
_cell_length_c                   18.634(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.884(9)
_cell_angle_gamma                90
_cell_volume                     1475.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2877
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      20.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_T_max  1.0138
_exptl_absorpt_process_details   
; 
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            6461
_diffrn_reflns_av_unetI/netI     0.1372
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         25.615
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2769
_reflns_number_gt                1388
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          
; 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²] 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         2769
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.824
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2650(6) 0.0277(3) 0.4287(2) 0.0391(10) Uani 1 1 d . . . . .
C2 C 0.2652(6) 0.0044(3) 0.3518(2) 0.0377(9) Uani 1 1 d . . . . .
C3 C 0.0666(6) 0.3202(3) 0.5701(2) 0.0485(11) Uani 1 1 d . . . . .
H3A H 0.0706 0.3604 0.5236 0.073 Uiso 1 1 calc R U . . .
H3B H 0.0525 0.3798 0.6075 0.073 Uiso 1 1 calc R U . . .
H3C H -0.0410 0.2651 0.5664 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2963(6) 0.1608(3) 0.68174(19) 0.0441(10) Uani 1 1 d . . . . .
H4A H 0.1716 0.1268 0.6868 0.066 Uiso 1 1 calc R U . . .
H4B H 0.3306 0.2184 0.7207 0.066 Uiso 1 1 calc R U . . .
H4C H 0.3909 0.0969 0.6846 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5034(6) 0.3221(3) 0.5802(2) 0.0492(11) Uani 1 1 d . . . . .
H5A H 0.6148 0.2704 0.5895 0.074 Uiso 1 1 calc R U . . .
H5B H 0.5167 0.3899 0.6136 0.074 Uiso 1 1 calc R U . . .
H5C H 0.4927 0.3513 0.5304 0.074 Uiso 1 1 calc R U . . .
C6 C -0.0864(6) -0.1337(3) 0.1431(2) 0.0480(11) Uani 1 1 d . . . . .
H6A H -0.1624 -0.1262 0.1834 0.072 Uiso 1 1 calc R U . . .
H6B H -0.1453 -0.1921 0.1083 0.072 Uiso 1 1 calc R U . . .
H6C H -0.0796 -0.0561 0.1193 0.072 Uiso 1 1 calc R U . . .
C7 C 0.1635(7) -0.3312(3) 0.2227(2) 0.0504(11) Uani 1 1 d . . . . .
H7A H 0.2923 -0.3457 0.2461 0.076 Uiso 1 1 calc R U . . .
H7B H 0.1288 -0.3935 0.1866 0.076 Uiso 1 1 calc R U . . .
H7C H 0.0748 -0.3324 0.2590 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3259(6) -0.1682(4) 0.1122(2) 0.0545(12) Uani 1 1 d . . . . .
H8A H 0.3280 -0.0853 0.0956 0.082 Uiso 1 1 calc R U . . .
H8B H 0.2896 -0.2206 0.0707 0.082 Uiso 1 1 calc R U . . .
H8C H 0.4520 -0.1906 0.1353 0.082 Uiso 1 1 calc R U . . .
N1 N 0.2906(5) 0.1356(3) 0.45797(16) 0.0423(8) Uani 1 1 d . . . . .
N2 N 0.2793(5) 0.1152(3) 0.52825(16) 0.0404(8) Uani 1 1 d . . . . .
N3 N 0.2461(5) -0.0006(3) 0.54135(17) 0.0457(9) Uani 1 1 d . . . . .
N4 N 0.2389(5) -0.0564(3) 0.47835(17) 0.0465(9) Uani 1 1 d . . . . .
N5 N 0.2059(5) -0.0973(3) 0.32068(16) 0.0403(8) Uani 1 1 d . . . . .
N6 N 0.2292(5) -0.0790(2) 0.25065(16) 0.0403(8) Uani 1 1 d . . . . .
N7 N 0.3001(5) 0.0313(3) 0.24077(17) 0.0437(8) Uani 1 1 d . . . . .
N8 N 0.3246(5) 0.0841(3) 0.30465(16) 0.0434(9) Uani 1 1 d . . . . .
Si1 Si 0.28820(18) 0.23638(9) 0.59400(6) 0.0411(3) Uani 1 1 d . . . . .
Si2 Si 0.15362(18) -0.18344(9) 0.17753(6) 0.0444(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 1.331(4) . ?
C1 N4 1.350(4) . ?
C1 C2 1.456(5) . ?
C2 N5 1.325(4) . ?
C2 N8 1.356(4) . ?
C3 Si1 1.844(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 Si1 1.836(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 Si1 1.851(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 Si2 1.837(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 Si2 1.855(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si2 1.836(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 N2 1.341(4) . ?
N2 N3 1.347(4) . ?
N2 Si1 1.826(3) . ?
N3 N4 1.326(4) . ?
N5 N6 1.351(4) . ?
N6 N7 1.357(4) . ?
N6 Si2 1.828(3) . ?
N7 N8 1.322(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 112.2(3) . . ?
N1 C1 C2 123.4(3) . . ?
N4 C1 C2 124.4(3) . . ?
N5 C2 N8 113.0(3) . . ?
N5 C2 C1 123.2(3) . . ?
N8 C2 C1 123.8(3) . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si2 C6 H6A 109.5 . . ?
Si2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si2 C7 H7A 109.5 . . ?
Si2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si2 C8 H8A 109.5 . . ?
Si2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 N2 103.0(3) . . ?
N1 N2 N3 111.9(3) . . ?
N1 N2 Si1 121.8(2) . . ?
N3 N2 Si1 126.0(2) . . ?
N4 N3 N2 106.5(3) . . ?
N3 N4 C1 106.4(3) . . ?
C2 N5 N6 102.9(3) . . ?
N5 N6 N7 111.1(3) . . ?
N5 N6 Si2 124.3(2) . . ?
N7 N6 Si2 124.3(2) . . ?
N8 N7 N6 107.3(3) . . ?
N7 N8 C2 105.7(3) . . ?
N2 Si1 C4 104.41(16) . . ?
N2 Si1 C3 104.93(18) . . ?
C4 Si1 C3 112.67(18) . . ?
N2 Si1 C5 104.83(16) . . ?
C4 Si1 C5 115.1(2) . . ?
C3 Si1 C5 113.51(19) . . ?
N6 Si2 C8 105.97(17) . . ?
N6 Si2 C6 104.09(16) . . ?
C8 Si2 C6 114.0(2) . . ?
N6 Si2 C7 104.03(17) . . ?
C8 Si2 C7 113.04(19) . . ?
C6 Si2 C7 114.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N5 -167.2(4) . . . . ?
N4 C1 C2 N5 12.7(6) . . . . ?
N1 C1 C2 N8 12.4(6) . . . . ?
N4 C1 C2 N8 -167.7(4) . . . . ?
N4 C1 N1 N2 0.0(4) . . . . ?
C2 C1 N1 N2 179.9(4) . . . . ?
C1 N1 N2 N3 -0.6(4) . . . . ?
C1 N1 N2 Si1 -175.6(3) . . . . ?
N1 N2 N3 N4 1.0(4) . . . . ?
Si1 N2 N3 N4 175.8(3) . . . . ?
N2 N3 N4 C1 -1.0(4) . . . . ?
N1 C1 N4 N3 0.6(4) . . . . ?
C2 C1 N4 N3 -179.3(4) . . . . ?
N8 C2 N5 N6 -0.3(4) . . . . ?
C1 C2 N5 N6 179.4(3) . . . . ?
C2 N5 N6 N7 -0.2(4) . . . . ?
C2 N5 N6 Si2 -174.7(3) . . . . ?
N5 N6 N7 N8 0.7(4) . . . . ?
Si2 N6 N7 N8 175.1(3) . . . . ?
N6 N7 N8 C2 -0.8(4) . . . . ?
N5 C2 N8 N7 0.7(4) . . . . ?
C1 C2 N8 N7 -178.9(4) . . . . ?
N1 N2 Si1 C4 -173.4(3) . . . . ?
N3 N2 Si1 C4 12.3(4) . . . . ?
N1 N2 Si1 C3 67.9(3) . . . . ?
N3 N2 Si1 C3 -106.4(3) . . . . ?
N1 N2 Si1 C5 -52.0(3) . . . . ?
N3 N2 Si1 C5 133.8(3) . . . . ?
N5 N6 Si2 C8 -147.4(3) . . . . ?
N7 N6 Si2 C8 38.9(4) . . . . ?
N5 N6 Si2 C6 92.1(3) . . . . ?
N7 N6 Si2 C6 -81.6(3) . . . . ?
N5 N6 Si2 C7 -28.0(3) . . . . ?
N7 N6 Si2 C7 158.3(3) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050

_exptl_crystal_recrystallization_method Sublimation
_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Hygroscopic'
####################################################################### 
# 
# 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_AVD94
_database_code_depnum_ccdc_archive 'CCDC 1527276'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Tetrabutylammonium bis(2,3-oxypyrazine)borate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 B N4 O4, C16 H36 N'
_chemical_formula_sum            'C24 H40 B N5 O4'
_chemical_formula_weight         473.42

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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.7012(7)
_cell_length_b                   16.4098(10)
_cell_length_c                   15.3653(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.945(2)
_cell_angle_gamma                90
_cell_volume                     2618.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.4414
_cell_measurement_theta_max      27.9006

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            61767
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         27.955
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6261
_reflns_number_gt                4937
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR92 (A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, 
G. Polidori, M. Camalli, J. Appl. Cryst. 1994, 27, 435.)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, 
Kreuzherrenstr. 102, 53227 Bonn, Germany)
;
_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
;
_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)+(0.0527P)²+1.1840P] 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         6261
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1084
_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 0.40494(13) 0.36806(8) 0.18346(9) 0.0184(3) Uani 1 1 d . . . . .
C2 C 0.29059(13) 0.41109(8) 0.14393(9) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.36162(16) 0.42826(9) 0.02059(10) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.3517 0.4494 -0.0382 0.034 Uiso 1 1 calc R U . . .
C4 C 0.47147(16) 0.38645(9) 0.05833(11) 0.0275(3) Uani 1 1 d . . . . .
H4 H 0.5338 0.3795 0.0242 0.033 Uiso 1 1 calc R U . . .
C5 C 0.23333(12) 0.39323(8) 0.41778(9) 0.0175(3) Uani 1 1 d . . . . .
C6 C 0.17642(13) 0.31799(8) 0.38384(9) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.10569(15) 0.30404(9) 0.50788(11) 0.0268(3) Uani 1 1 d . . . . .
H7 H 0.0615 0.2739 0.5440 0.032 Uiso 1 1 calc R U . . .
C8 C 0.15824(15) 0.37723(9) 0.53933(10) 0.0260(3) Uani 1 1 d . . . . .
H8 H 0.1474 0.3959 0.5956 0.031 Uiso 1 1 calc R U . . .
C9 C 0.28000(12) 0.18274(8) 0.12200(9) 0.0172(3) Uani 1 1 d . . . . .
H9A H 0.3338 0.2190 0.0945 0.021 Uiso 1 1 calc R U . . .
H9B H 0.2642 0.2115 0.1750 0.021 Uiso 1 1 calc R U . . .
C10 C 0.35718(13) 0.10637(8) 0.15453(10) 0.0205(3) Uani 1 1 d . . . . .
H10A H 0.3829 0.0796 0.1038 0.025 Uiso 1 1 calc R U . . .
H10B H 0.3038 0.0676 0.1793 0.025 Uiso 1 1 calc R U . . .
C11 C 0.47711(13) 0.12935(9) 0.22702(9) 0.0212(3) Uani 1 1 d . . . . .
H11A H 0.5325 0.1654 0.2007 0.025 Uiso 1 1 calc R U . . .
H11B H 0.4508 0.1601 0.2751 0.025 Uiso 1 1 calc R U . . .
C12 C 0.55414(15) 0.05463(10) 0.26742(11) 0.0304(3) Uani 1 1 d . . . . .
H12A H 0.4998 0.0189 0.2938 0.046 Uiso 1 1 calc R U . . .
H12B H 0.6291 0.0718 0.3141 0.046 Uiso 1 1 calc R U . . .
H12C H 0.5831 0.0251 0.2204 0.046 Uiso 1 1 calc R U . . .
C13 C 0.06690(13) 0.11093(8) 0.08937(9) 0.0167(3) Uani 1 1 d . . . . .
H13A H -0.0160 0.1059 0.0441 0.020 Uiso 1 1 calc R U . . .
H13B H 0.1094 0.0570 0.0944 0.020 Uiso 1 1 calc R U . . .
C14 C 0.03813(15) 0.13097(9) 0.17895(10) 0.0233(3) Uani 1 1 d . . . . .
H14A H -0.0156 0.1807 0.1734 0.028 Uiso 1 1 calc R U . . .
H14B H 0.1194 0.1412 0.2244 0.028 Uiso 1 1 calc R U . . .
C15 C -0.03304(14) 0.05913(9) 0.20774(10) 0.0225(3) Uani 1 1 d . . . . .
H15A H -0.1140 0.0498 0.1616 0.027 Uiso 1 1 calc R U . . .
H15B H 0.0206 0.0096 0.2107 0.027 Uiso 1 1 calc R U . . .
C16 C -0.06482(18) 0.07154(10) 0.29780(12) 0.0353(4) Uani 1 1 d . . . . .
H16A H 0.0146 0.0820 0.3437 0.053 Uiso 1 1 calc R U . . .
H16B H -0.1066 0.0225 0.3137 0.053 Uiso 1 1 calc R U . . .
H16C H -0.1231 0.1182 0.2942 0.053 Uiso 1 1 calc R U . . .
C17 C 0.16868(13) 0.13608(8) -0.03306(9) 0.0178(3) Uani 1 1 d . . . . .
H17A H 0.2199 0.0854 -0.0193 0.021 Uiso 1 1 calc R U . . .
H17B H 0.0829 0.1207 -0.0702 0.021 Uiso 1 1 calc R U . . .
C18 C 0.23367(14) 0.19073(8) -0.08894(9) 0.0211(3) Uani 1 1 d . . . . .
H18A H 0.3113 0.2161 -0.0501 0.025 Uiso 1 1 calc R U . . .
H18B H 0.1740 0.2347 -0.1169 0.025 Uiso 1 1 calc R U . . .
C19 C 0.27147(16) 0.13983(10) -0.16144(10) 0.0289(3) Uani 1 1 d . . . . .
H19A H 0.3395 0.1007 -0.1328 0.035 Uiso 1 1 calc R U . . .
H19B H 0.1958 0.1081 -0.1938 0.035 Uiso 1 1 calc R U . . .
C20 C 0.32038(17) 0.19164(11) -0.22852(11) 0.0355(4) Uani 1 1 d . . . . .
H20A H 0.2504 0.2262 -0.2619 0.053 Uiso 1 1 calc R U . . .
H20B H 0.3508 0.1560 -0.2703 0.053 Uiso 1 1 calc R U . . .
H20C H 0.3915 0.2261 -0.1964 0.053 Uiso 1 1 calc R U . . .
C21 C 0.08988(13) 0.25561(8) 0.04162(9) 0.0175(3) Uani 1 1 d . . . . .
H21A H 0.0833 0.2765 0.1008 0.021 Uiso 1 1 calc R U . . .
H21B H 0.1481 0.2925 0.0191 0.021 Uiso 1 1 calc R U . . .
C22 C -0.04263(13) 0.25957(8) -0.02222(10) 0.0212(3) Uani 1 1 d . . . . .
H22A H -0.1043 0.2272 0.0024 0.025 Uiso 1 1 calc R U . . .
H22B H -0.0390 0.2358 -0.0808 0.025 Uiso 1 1 calc R U . . .
C23 C -0.08913(15) 0.34820(8) -0.03558(10) 0.0236(3) Uani 1 1 d . . . . .
H23A H -0.0222 0.3814 -0.0534 0.028 Uiso 1 1 calc R U . . .
H23B H -0.1678 0.3504 -0.0851 0.028 Uiso 1 1 calc R U . . .
C24 C -0.11843(17) 0.38522(10) 0.04796(11) 0.0333(4) Uani 1 1 d . . . . .
H24A H -0.1847 0.3527 0.0661 0.050 Uiso 1 1 calc R U . . .
H24B H -0.1495 0.4412 0.0351 0.050 Uiso 1 1 calc R U . . .
H24C H -0.0400 0.3857 0.0966 0.050 Uiso 1 1 calc R U . . .
N1 N 0.49655(12) 0.35400(7) 0.14292(8) 0.0239(3) Uani 1 1 d . . . . .
N2 N 0.26478(13) 0.44122(8) 0.06349(8) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.22611(11) 0.42519(7) 0.49362(8) 0.0219(3) Uani 1 1 d . . . . .
N4 N 0.11307(12) 0.27162(7) 0.42706(9) 0.0239(3) Uani 1 1 d . . . . .
N5 N 0.15084(10) 0.17139(6) 0.05469(7) 0.0152(2) Uani 1 1 d . . . . .
O1 O 0.40280(9) 0.34267(6) 0.26616(6) 0.0191(2) Uani 1 1 d . . . . .
O2 O 0.21191(9) 0.41342(6) 0.20005(7) 0.0233(2) Uani 1 1 d . . . . .
O3 O 0.20095(9) 0.30154(6) 0.30409(7) 0.0214(2) Uani 1 1 d . . . . .
O4 O 0.29910(9) 0.42509(6) 0.36179(6) 0.0194(2) Uani 1 1 d . . . . .
B1 B 0.27843(15) 0.37045(9) 0.28267(10) 0.0184(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 1.3026(18) . ?
C1 O1 1.3427(16) . ?
C1 C2 1.4166(19) . ?
C2 N2 1.2977(19) . ?
C2 O2 1.3430(17) . ?
C3 C4 1.364(2) . ?
C3 N2 1.372(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.370(2) . ?
C4 H4 0.9500 . ?
C5 N3 1.2971(18) . ?
C5 O4 1.3418(16) . ?
C5 C6 1.4191(18) . ?
C6 N4 1.3024(18) . ?
C6 O3 1.3410(16) . ?
C7 C8 1.364(2) . ?
C7 N4 1.371(2) . ?
C7 H7 0.9500 . ?
C8 N3 1.3733(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.5178(18) . ?
C9 N5 1.5251(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5300(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5170(19) . ?
C13 N5 1.5186(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5258(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.516(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5208(18) . ?
C17 N5 1.5213(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5229(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5188(19) . ?
C21 N5 1.5206(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5348(19) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.520(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1 B1 1.4854(18) . ?
O2 B1 1.4764(18) . ?
O3 B1 1.4853(18) . ?
O4 B1 1.4837(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 O1 125.74(13) . . ?
N1 C1 C2 123.72(13) . . ?
O1 C1 C2 110.51(12) . . ?
N2 C2 O2 125.32(13) . . ?
N2 C2 C1 124.19(13) . . ?
O2 C2 C1 110.45(12) . . ?
C4 C3 N2 123.16(14) . . ?
C4 C3 H3 118.4 . . ?
N2 C3 H3 118.4 . . ?
C3 C4 N1 123.41(14) . . ?
C3 C4 H4 118.3 . . ?
N1 C4 H4 118.3 . . ?
N3 C5 O4 124.92(12) . . ?
N3 C5 C6 124.66(12) . . ?
O4 C5 C6 110.39(11) . . ?
N4 C6 O3 126.07(12) . . ?
N4 C6 C5 123.43(13) . . ?
O3 C6 C5 110.47(11) . . ?
C8 C7 N4 123.62(13) . . ?
C8 C7 H7 118.2 . . ?
N4 C7 H7 118.2 . . ?
C7 C8 N3 123.16(14) . . ?
C7 C8 H8 118.4 . . ?
N3 C8 H8 118.4 . . ?
C10 C9 N5 117.05(10) . . ?
C10 C9 H9A 108.0 . . ?
N5 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
N5 C9 H9B 108.0 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 C11 109.30(11) . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C10 112.01(12) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N5 116.31(11) . . ?
C14 C13 H13A 108.2 . . ?
N5 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
N5 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 108.67(11) . . ?
C13 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 C14 113.48(13) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N5 116.61(11) . . ?
C18 C17 H17A 108.1 . . ?
N5 C17 H17A 108.1 . . ?
C18 C17 H17B 108.1 . . ?
N5 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 C19 109.14(11) . . ?
C17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 C18 112.59(13) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
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 . . ?
C22 C21 N5 115.35(10) . . ?
C22 C21 H21A 108.4 . . ?
N5 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
N5 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 110.43(11) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 113.09(12) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C4 112.76(13) . . ?
C2 N2 C3 112.74(13) . . ?
C5 N3 C8 112.40(12) . . ?
C6 N4 C7 112.70(12) . . ?
C13 N5 C21 111.65(10) . . ?
C13 N5 C17 105.86(10) . . ?
C21 N5 C17 111.76(10) . . ?
C13 N5 C9 110.96(10) . . ?
C21 N5 C9 105.57(9) . . ?
C17 N5 C9 111.15(10) . . ?
C1 O1 B1 106.66(10) . . ?
C2 O2 B1 106.95(11) . . ?
C6 O3 B1 106.97(10) . . ?
C5 O4 B1 106.99(10) . . ?
O2 B1 O4 111.21(11) . . ?
O2 B1 O3 112.02(11) . . ?
O4 B1 O3 105.04(11) . . ?
O2 B1 O1 105.42(11) . . ?
O4 B1 O1 111.26(11) . . ?
O3 B1 O1 112.04(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
N1 C1 C2 N2 -0.1(2) . . . . ?
O1 C1 C2 N2 -178.47(13) . . . . ?
N1 C1 C2 O2 177.61(12) . . . . ?
O1 C1 C2 O2 -0.72(16) . . . . ?
N2 C3 C4 N1 -0.7(2) . . . . ?
N3 C5 C6 N4 -1.9(2) . . . . ?
O4 C5 C6 N4 176.03(13) . . . . ?
N3 C5 C6 O3 -179.99(13) . . . . ?
O4 C5 C6 O3 -2.08(15) . . . . ?
N4 C7 C8 N3 -1.2(3) . . . . ?
N5 C9 C10 C11 -175.22(11) . . . . ?
C9 C10 C11 C12 175.91(12) . . . . ?
N5 C13 C14 C15 -173.35(11) . . . . ?
C13 C14 C15 C16 178.87(13) . . . . ?
N5 C17 C18 C19 166.87(12) . . . . ?
C17 C18 C19 C20 172.06(13) . . . . ?
N5 C21 C22 C23 -175.51(11) . . . . ?
C21 C22 C23 C24 -68.59(17) . . . . ?
O1 C1 N1 C4 179.05(12) . . . . ?
C2 C1 N1 C4 0.98(19) . . . . ?
C3 C4 N1 C1 -0.6(2) . . . . ?
O2 C2 N2 C3 -178.49(13) . . . . ?
C1 C2 N2 C3 -1.1(2) . . . . ?
C4 C3 N2 C2 1.4(2) . . . . ?
O4 C5 N3 C8 -176.60(13) . . . . ?
C6 C5 N3 C8 1.0(2) . . . . ?
C7 C8 N3 C5 0.4(2) . . . . ?
O3 C6 N4 C7 178.81(13) . . . . ?
C5 C6 N4 C7 1.0(2) . . . . ?
C8 C7 N4 C6 0.4(2) . . . . ?
C14 C13 N5 C21 -60.11(14) . . . . ?
C14 C13 N5 C17 178.06(11) . . . . ?
C14 C13 N5 C9 57.36(14) . . . . ?
C22 C21 N5 C13 -58.21(14) . . . . ?
C22 C21 N5 C17 60.15(14) . . . . ?
C22 C21 N5 C9 -178.89(11) . . . . ?
C18 C17 N5 C13 171.52(11) . . . . ?
C18 C17 N5 C21 49.76(15) . . . . ?
C18 C17 N5 C9 -67.90(14) . . . . ?
C10 C9 N5 C13 53.31(15) . . . . ?
C10 C9 N5 C21 174.44(11) . . . . ?
C10 C9 N5 C17 -64.21(14) . . . . ?
N1 C1 O1 B1 -178.10(13) . . . . ?
C2 C1 O1 B1 0.19(14) . . . . ?
N2 C2 O2 B1 178.62(14) . . . . ?
C1 C2 O2 B1 0.90(15) . . . . ?
N4 C6 O3 B1 -178.52(14) . . . . ?
C5 C6 O3 B1 -0.47(15) . . . . ?
N3 C5 O4 B1 -178.45(13) . . . . ?
C6 C5 O4 B1 3.65(14) . . . . ?
C2 O2 B1 O4 119.94(12) . . . . ?
C2 O2 B1 O3 -122.86(12) . . . . ?
C2 O2 B1 O1 -0.76(14) . . . . ?
C5 O4 B1 O2 117.59(12) . . . . ?
C5 O4 B1 O3 -3.79(14) . . . . ?
C5 O4 B1 O1 -125.22(11) . . . . ?
C6 O3 B1 O2 -118.28(12) . . . . ?
C6 O3 B1 O4 2.56(14) . . . . ?
C6 O3 B1 O1 123.48(12) . . . . ?
C1 O1 B1 O2 0.34(13) . . . . ?
C1 O1 B1 O4 -120.32(12) . . . . ?
C1 O1 B1 O3 122.43(12) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_fin289
_database_code_depnum_ccdc_archive 'CCDC 1484827'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'
_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 B N8 O4, C6 H14 N'
_chemical_formula_sum            'C18 H14 B N9 O4'
_chemical_formula_weight         431.19

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                   10.1140(6)
_cell_length_b                   11.7988(7)
_cell_length_c                   17.7771(10)
_cell_angle_alpha                87.703(2)
_cell_angle_beta                 74.253(2)
_cell_angle_gamma                79.855(2)
_cell_volume                     2009.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            22424
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         27.151
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8855
_reflns_number_gt                5996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
SIR2011 (M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, C. Giacovazzo, M. Mallamo, A. Mazzone, G. Polidori, 
R. Spagna, J. Appl. Cryst. 2012, 45, 357-361)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. 
Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 
102, 53227 Bonn, Germany)
;


_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
;
_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)+(0.0351P)²+0.6834P] 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         8855
_refine_ls_number_parameters     730
_refine_ls_number_restraints     149
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.72784(18) 0.79115(15) 0.94869(11) 0.0146(4) Uani 1 1 d . . . . .
C2 C 0.84275(18) 0.84759(15) 0.91392(10) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.64229(19) 0.93248(16) 1.03600(11) 0.0172(4) Uani 1 1 d . . . . .
C4 C 0.75353(19) 0.98735(15) 1.00211(11) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.5338(2) 0.98316(17) 1.10231(12) 0.0230(4) Uani 1 1 d . . . . .
C6 C 0.7633(2) 1.09532(17) 1.03339(11) 0.0216(4) Uani 1 1 d . . . . .
C7 C 0.98097(18) 0.51714(15) 0.78331(10) 0.0150(4) Uani 1 1 d . . . . .
C8 C 0.90086(19) 0.58133(15) 0.73578(11) 0.0172(4) Uani 1 1 d . . . . .
C9 C 1.0495(2) 0.37685(16) 0.69471(11) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.9691(2) 0.43775(17) 0.65032(12) 0.0243(5) Uani 1 1 d . U . . .
C11 C 1.1286(2) 0.26479(17) 0.66936(12) 0.0249(5) Uani 1 1 d . . . . .
C13 C 0.12503(18) 0.99244(15) 0.78047(11) 0.0152(4) Uani 1 1 d . . . . .
C14 C 0.0022(2) 1.00974(15) 0.75406(11) 0.0179(4) Uani 1 1 d . . . . .
C15 C 0.03829(18) 1.14794(15) 0.85476(10) 0.0142(4) Uani 1 1 d . . . . .
C16 C -0.08030(19) 1.16510(15) 0.82910(11) 0.0158(4) Uani 1 1 d . . . . .
C17 C 0.05509(18) 1.22671(15) 0.91027(11) 0.0146(4) Uani 1 1 d . . . . .
C18 C -0.1883(2) 1.26307(17) 0.85584(12) 0.0212(4) Uani 1 1 d . . . . .
O7 O 0.14658(14) 0.73351(10) 0.69627(7) 0.0206(3) Uani 1 1 d . . . . .
O8 O 0.23575(17) 0.87184(11) 0.60662(8) 0.0347(4) Uani 1 1 d . . . . .
C19 C 0.2132(2) 0.68527(16) 0.62738(11) 0.0242(5) Uani 1 1 d . . . . .
C20 C 0.2661(3) 0.76935(17) 0.57316(12) 0.0371(6) Uani 1 1 d . . . . .
N13 N 0.2292(2) 0.57658(14) 0.61100(10) 0.0293(4) Uani 1 1 d . . . . .
C31 C 0.28855(19) 0.59641(16) 0.81986(11) 0.0180(4) Uani 1 1 d . . . . .
H31A H 0.2077 0.6568 0.8430 0.022 Uiso 1 1 calc R U . . .
H31B H 0.2630 0.5504 0.7823 0.022 Uiso 1 1 calc R U . . .
C32 C 0.41487(19) 0.65077(17) 0.77887(12) 0.0231(5) Uani 1 1 d . . . . .
H32A H 0.3930 0.7355 0.7856 0.028 Uiso 1 1 calc R U . . .
H32B H 0.4443 0.6322 0.7223 0.028 Uiso 1 1 calc R U . . .
C34 C 0.5296(2) 0.59948(18) 0.81748(12) 0.0258(5) Uani 1 1 d . . . . .
H34A H 0.5902 0.5318 0.7877 0.031 Uiso 1 1 calc R U . . .
H34B H 0.5877 0.6572 0.8213 0.031 Uiso 1 1 calc R U . . .
C35 C 0.45140(19) 0.56501(18) 0.89742(11) 0.0225(5) Uani 1 1 d . . . . .
H35A H 0.4190 0.6321 0.9335 0.027 Uiso 1 1 calc R U . . .
H35B H 0.5108 0.5047 0.9197 0.027 Uiso 1 1 calc R U . . .
C36 C 0.2119(2) 0.52655(17) 0.95613(11) 0.0235(5) Uani 1 1 d . . . . .
H36A H 0.1334 0.4987 0.9450 0.035 Uiso 1 1 calc R U . . .
H36B H 0.1826 0.6067 0.9743 0.035 Uiso 1 1 calc R U . . .
H36C H 0.2425 0.4789 0.9967 0.035 Uiso 1 1 calc R U . . .
C37 C 0.3735(2) 0.39752(16) 0.85549(12) 0.0262(5) Uani 1 1 d . . . . .
H37A H 0.4061 0.3497 0.8955 0.039 Uiso 1 1 calc R U . . .
H37B H 0.4492 0.3931 0.8071 0.039 Uiso 1 1 calc R U . . .
H37C H 0.2941 0.3696 0.8455 0.039 Uiso 1 1 calc R U . . .
B1 B 0.8696(2) 0.68472(18) 0.84572(13) 0.0168(5) Uani 1 1 d . . . . .
B2 B 0.1509(3) 0.85881(19) 0.68859(13) 0.0227(5) Uani 1 1 d . . . . .
N1 N 0.62639(15) 0.82982(13) 1.00891(9) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.85895(16) 0.94533(13) 0.93820(9) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.4471(2) 1.02649(16) 1.15358(11) 0.0364(5) Uani 1 1 d . . . . .
N4 N 0.77143(19) 1.18168(15) 1.05763(10) 0.0317(4) Uani 1 1 d . . . . .
N5 N 1.05636(16) 0.41646(13) 0.76479(9) 0.0172(3) Uani 1 1 d . . . . .
N6 N 0.89115(17) 0.54474(14) 0.66994(9) 0.0242(4) Uani 1 1 d . . . . .
N7 N 1.1895(2) 0.17525(15) 0.64839(11) 0.0356(5) Uani 1 1 d . . . . .
N9 N 0.14686(15) 1.05906(13) 0.83036(9) 0.0163(3) Uani 1 1 d . . . . .
N10 N -0.10150(17) 1.09396(13) 0.77604(9) 0.0201(4) Uani 1 1 d . . . . .
N11 N 0.06922(16) 1.28815(13) 0.95449(10) 0.0208(4) Uani 1 1 d . . . . .
N12 N -0.27186(19) 1.34284(16) 0.87665(11) 0.0337(5) Uani 1 1 d . . . . .
N18 N 0.32959(15) 0.51958(13) 0.88351(9) 0.0166(3) Uani 1 1 d . . . . .
O1 O 0.73986(12) 0.69353(10) 0.91101(7) 0.0175(3) Uani 1 1 d . . . . .
O2 O 0.92966(12) 0.78727(11) 0.85387(7) 0.0178(3) Uani 1 1 d . . . . .
O3 O 0.96557(12) 0.57494(10) 0.84819(7) 0.0171(3) Uani 1 1 d . . . . .
O4 O 0.83701(13) 0.68190(10) 0.76919(7) 0.0182(3) Uani 1 1 d . . . . .
O5 O 0.21382(13) 0.90143(11) 0.74495(7) 0.0201(3) Uani 1 1 d . . . . .
O6 O 0.01121(15) 0.92940(11) 0.70147(8) 0.0244(3) Uani 1 1 d . . . . .
N17 N 0.3042(12) 0.0881(7) 0.3837(8) 0.0155(18) Uani 0.502(2) 1 d D . P A 1
C25 C 0.3723(5) 0.0463(3) 0.4481(2) 0.0230(10) Uani 0.502(2) 1 d D . P A 1
H25A H 0.4078 0.1093 0.4674 0.028 Uiso 0.502(2) 1 calc R U P A 1
H25B H 0.3059 0.0154 0.4923 0.028 Uiso 0.502(2) 1 calc R U P A 1
C26 C 0.4887(4) -0.0459(4) 0.4094(3) 0.0321(11) Uani 0.502(2) 1 d D . P A 1
H26A H 0.5012 -0.1092 0.4465 0.039 Uiso 0.502(2) 1 calc R U P A 1
H26B H 0.5768 -0.0148 0.3917 0.039 Uiso 0.502(2) 1 calc R U P A 1
C27 C 0.4505(5) -0.0910(3) 0.3383(3) 0.0327(11) Uani 0.502(2) 1 d D . P A 1
H27A H 0.5169 -0.0749 0.2884 0.039 Uiso 0.502(2) 1 calc R U P A 1
H27B H 0.4495 -0.1748 0.3421 0.039 Uiso 0.502(2) 1 calc R U P A 1
C28 C 0.3041(9) -0.0226(6) 0.3448(5) 0.0268(18) Uani 0.502(2) 1 d D . P A 1
H28A H 0.2877 -0.0082 0.2925 0.032 Uiso 0.502(2) 1 calc R U P A 1
H28B H 0.2315 -0.0641 0.3770 0.032 Uiso 0.502(2) 1 calc R U P A 1
C29 C 0.1612(4) 0.1529(4) 0.4144(3) 0.0289(11) Uani 0.502(2) 1 d D . P A 1
H29A H 0.1210 0.1774 0.3708 0.043 Uiso 0.502(2) 1 calc R U P A 1
H29B H 0.1643 0.2208 0.4434 0.043 Uiso 0.502(2) 1 calc R U P A 1
H29C H 0.1034 0.1035 0.4493 0.043 Uiso 0.502(2) 1 calc R U P A 1
C30 C 0.3905(4) 0.1632(4) 0.3281(2) 0.0263(10) Uani 0.502(2) 1 d D . P A 1
H30A H 0.4860 0.1214 0.3085 0.039 Uiso 0.502(2) 1 calc R U P A 1
H30B H 0.3918 0.2334 0.3554 0.039 Uiso 0.502(2) 1 calc R U P A 1
H30C H 0.3501 0.1837 0.2841 0.039 Uiso 0.502(2) 1 calc R U P A 1
N17A N 0.3281(13) 0.0570(8) 0.3843(8) 0.0174(19) Uani 0.498(2) 1 d D . P A 2
C25A C 0.2816(10) -0.0504(7) 0.3655(5) 0.028(2) Uani 0.498(2) 1 d D . P A 2
H25C H 0.2708 -0.0472 0.3117 0.034 Uiso 0.498(2) 1 calc R U P A 2
H25D H 0.3504 -0.1195 0.3700 0.034 Uiso 0.498(2) 1 calc R U P A 2
C26A C 0.1447(4) -0.0542(3) 0.4239(2) 0.0264(10) Uani 0.498(2) 1 d D . P A 2
H26C H 0.1474 -0.1286 0.4517 0.032 Uiso 0.498(2) 1 calc R U P A 2
H26D H 0.0692 -0.0457 0.3973 0.032 Uiso 0.498(2) 1 calc R U P A 2
C27A C 0.1185(4) 0.0457(4) 0.4818(3) 0.0358(12) Uani 0.498(2) 1 d D . P A 2
H27C H 0.0528 0.1118 0.4695 0.043 Uiso 0.498(2) 1 calc R U P A 2
H27D H 0.0806 0.0211 0.5362 0.043 Uiso 0.498(2) 1 calc R U P A 2
C28A C 0.2615(5) 0.0762(4) 0.4704(2) 0.0265(10) Uani 0.498(2) 1 d D . P A 2
H28C H 0.2549 0.1574 0.4852 0.032 Uiso 0.498(2) 1 calc R U P A 2
H28D H 0.3150 0.0257 0.5017 0.032 Uiso 0.498(2) 1 calc R U P A 2
C29A C 0.4823(4) 0.0481(5) 0.3644(3) 0.0430(13) Uani 0.498(2) 1 d D . P A 2
H29D H 0.5055 0.1175 0.3826 0.064 Uiso 0.498(2) 1 calc R U P A 2
H29E H 0.5210 0.0405 0.3076 0.064 Uiso 0.498(2) 1 calc R U P A 2
H29F H 0.5221 -0.0197 0.3897 0.064 Uiso 0.498(2) 1 calc R U P A 2
C30A C 0.2746(5) 0.1578(3) 0.3393(2) 0.0250(10) Uani 0.498(2) 1 d D . P A 2
H30D H 0.1745 0.1613 0.3460 0.037 Uiso 0.498(2) 1 calc R U P A 2
H30E H 0.3241 0.1482 0.2837 0.037 Uiso 0.498(2) 1 calc R U P A 2
H30F H 0.2904 0.2292 0.3590 0.037 Uiso 0.498(2) 1 calc R U P A 2
N14 N 0.3034(16) 0.7509(5) 0.4990(3) 0.0205(19) Uani 0.49(2) 1 d D U P B 3
N15 N 0.3149(14) 0.3450(7) 0.4875(6) 0.0303(18) Uani 0.49(2) 1 d D U P B 3
N16 N 0.437(2) 0.5806(9) 0.3371(4) 0.065(4) Uani 0.49(2) 1 d D U P B 3
C21 C 0.2744(13) 0.5550(6) 0.5353(5) 0.0161(16) Uani 0.49(2) 1 d D U P B 3
C22 C 0.3189(16) 0.6362(6) 0.4815(3) 0.0218(19) Uani 0.49(2) 1 d D U P B 3
C23 C 0.2946(13) 0.4377(7) 0.5092(6) 0.0202(16) Uani 0.49(2) 1 d D U P B 3
C24 C 0.3843(19) 0.6045(7) 0.4007(4) 0.038(3) Uani 0.49(2) 1 d D U P B 3
N14A N 0.3618(12) 0.7449(4) 0.5020(3) 0.0172(14) Uani 0.51(2) 1 d D U P B 4
N15A N 0.3706(16) 0.3381(8) 0.4863(6) 0.041(2) Uani 0.51(2) 1 d D U P B 4
N16A N 0.5091(13) 0.5753(8) 0.3395(4) 0.046(2) Uani 0.51(2) 1 d D U P B 4
C21A C 0.3255(13) 0.5492(6) 0.5338(4) 0.0151(16) Uani 0.51(2) 1 d D U P B 4
C22A C 0.3776(13) 0.6312(5) 0.4827(3) 0.0166(15) Uani 0.51(2) 1 d D U P B 4
C23A C 0.3479(15) 0.4312(7) 0.5089(6) 0.0244(18) Uani 0.51(2) 1 d D U P B 4
C24A C 0.4507(13) 0.6020(6) 0.4024(3) 0.0265(18) Uani 0.51(2) 1 d D U P B 4
N8A N 0.986(3) 0.3492(7) 0.5175(7) 0.035(4) Uani 0.57(5) 1 d . U P C 3
C12A C 0.982(2) 0.3925(10) 0.5741(7) 0.021(2) Uani 0.57(5) 1 d . U P C 3
N8 N 0.925(2) 0.3424(8) 0.5292(6) 0.024(2) Uani 0.43(5) 1 d . U P C 4
C12 C 0.938(2) 0.3819(14) 0.5837(8) 0.019(2) Uani 0.43(5) 1 d . U P C 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 N1 1.298(2) . ?
C1 O1 1.326(2) . ?
C1 C2 1.423(2) . ?
C2 N2 1.299(2) . ?
C2 O2 1.323(2) . ?
C3 N1 1.372(2) . ?
C3 C4 1.380(3) . ?
C3 C5 1.440(3) . ?
C4 N2 1.369(2) . ?
C4 C6 1.440(3) . ?
C5 N3 1.143(2) . ?
C6 N4 1.147(2) . ?
C7 N5 1.295(2) . ?
C7 O3 1.322(2) . ?
C7 C8 1.431(2) . ?
C8 N6 1.298(2) . ?
C8 O4 1.325(2) . ?
C9 N5 1.371(2) . ?
C9 C10 1.377(3) . ?
C9 C11 1.439(3) . ?
C10 N6 1.368(2) . ?
C10 C12A 1.440(9) . ?
C10 C12 1.507(14) . ?
C11 N7 1.145(2) . ?
C13 N9 1.295(2) . ?
C13 O5 1.329(2) . ?
C13 C14 1.423(3) . ?
C14 N10 1.297(2) . ?
C14 O6 1.332(2) . ?
C15 N9 1.366(2) . ?
C15 C16 1.375(2) . ?
C15 C17 1.444(2) . ?
C16 N10 1.370(2) . ?
C16 C18 1.440(3) . ?
C17 N11 1.143(2) . ?
C18 N12 1.147(2) . ?
O7 C19 1.323(2) . ?
O7 B2 1.486(2) . ?
O8 C20 1.318(2) . ?
O8 B2 1.494(3) . ?
C19 N13 1.299(2) . ?
C19 C20 1.425(3) . ?
C20 N14 1.286(6) . ?
C20 N14A 1.373(7) . ?
N13 C21 1.317(8) . ?
N13 C21A 1.461(9) . ?
C31 N18 1.521(2) . ?
C31 C32 1.523(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C34 1.528(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C34 C35 1.506(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 N18 1.508(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N18 1.493(2) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 N18 1.494(2) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
B1 O2 1.475(2) . ?
B1 O3 1.482(2) . ?
B1 O4 1.487(2) . ?
B1 O1 1.488(2) . ?
B2 O5 1.470(3) . ?
B2 O6 1.472(3) . ?
N17 C29 1.480(11) . ?
N17 C30 1.503(10) . ?
N17 C28 1.503(14) . ?
N17 C25 1.513(13) . ?
C25 C26 1.487(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.557(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.533(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N17A C29A 1.488(13) . ?
N17A C28A 1.504(14) . ?
N17A C25A 1.506(14) . ?
N17A C30A 1.510(8) . ?
C25A C26A 1.494(9) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A C27A 1.536(6) . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
C27A C28A 1.510(6) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
C28A H28C 0.9900 . ?
C28A H28D 0.9900 . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
C30A H30D 0.9800 . ?
C30A H30E 0.9800 . ?
C30A H30F 0.9800 . ?
N14 C22 1.373(6) . ?
N15 C23 1.140(7) . ?
N16 C24 1.135(7) . ?
C21 C22 1.371(7) . ?
C21 C23 1.440(8) . ?
C22 C24 1.442(7) . ?
N14A C22A 1.368(6) . ?
N15A C23A 1.147(7) . ?
N16A C24A 1.141(6) . ?
C21A C22A 1.374(7) . ?
C21A C23A 1.439(7) . ?
C22A C24A 1.443(6) . ?
N8A C12A 1.137(8) . ?
N8 C12 1.140(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
N1 C1 O1 125.08(16) . . ?
N1 C1 C2 124.64(16) . . ?
O1 C1 C2 110.28(15) . . ?
N2 C2 O2 125.00(16) . . ?
N2 C2 C1 124.17(17) . . ?
O2 C2 C1 110.84(15) . . ?
N1 C3 C4 123.21(17) . . ?
N1 C3 C5 116.29(16) . . ?
C4 C3 C5 120.49(17) . . ?
N2 C4 C3 123.67(16) . . ?
N2 C4 C6 116.05(16) . . ?
C3 C4 C6 120.28(17) . . ?
N3 C5 C3 177.8(2) . . ?
N4 C6 C4 179.4(2) . . ?
N5 C7 O3 125.57(17) . . ?
N5 C7 C8 124.14(17) . . ?
O3 C7 C8 110.28(15) . . ?
N6 C8 O4 125.24(17) . . ?
N6 C8 C7 124.39(17) . . ?
O4 C8 C7 110.36(16) . . ?
N5 C9 C10 123.07(17) . . ?
N5 C9 C11 116.70(17) . . ?
C10 C9 C11 120.21(18) . . ?
N6 C10 C9 124.01(18) . . ?
N6 C10 C12A 117.9(5) . . ?
C9 C10 C12A 117.6(5) . . ?
N6 C10 C12 113.5(6) . . ?
C9 C10 C12 121.5(6) . . ?
N7 C11 C9 178.5(2) . . ?
N9 C13 O5 125.67(16) . . ?
N9 C13 C14 123.95(17) . . ?
O5 C13 C14 110.35(15) . . ?
N10 C14 O6 124.88(17) . . ?
N10 C14 C13 124.82(17) . . ?
O6 C14 C13 110.26(16) . . ?
N9 C15 C16 123.97(16) . . ?
N9 C15 C17 115.56(15) . . ?
C16 C15 C17 120.47(16) . . ?
N10 C16 C15 123.09(17) . . ?
N10 C16 C18 116.32(16) . . ?
C15 C16 C18 120.57(17) . . ?
N11 C17 C15 179.3(2) . . ?
N12 C18 C16 178.3(2) . . ?
C19 O7 B2 107.24(15) . . ?
C20 O8 B2 107.03(15) . . ?
N13 C19 O7 125.18(18) . . ?
N13 C19 C20 124.34(19) . . ?
O7 C19 C20 110.48(16) . . ?
N14 C20 O8 124.9(3) . . ?
O8 C20 N14A 122.9(3) . . ?
N14 C20 C19 121.9(3) . . ?
O8 C20 C19 110.76(18) . . ?
N14A C20 C19 124.8(3) . . ?
C19 N13 C21 112.6(3) . . ?
C19 N13 C21A 111.0(3) . . ?
N18 C31 C32 106.72(14) . . ?
N18 C31 H31A 110.4 . . ?
C32 C31 H31A 110.4 . . ?
N18 C31 H31B 110.4 . . ?
C32 C31 H31B 110.4 . . ?
H31A C31 H31B 108.6 . . ?
C31 C32 C34 105.79(15) . . ?
C31 C32 H32A 110.6 . . ?
C34 C32 H32A 110.6 . . ?
C31 C32 H32B 110.6 . . ?
C34 C32 H32B 110.6 . . ?
H32A C32 H32B 108.7 . . ?
C35 C34 C32 104.07(15) . . ?
C35 C34 H34A 110.9 . . ?
C32 C34 H34A 110.9 . . ?
C35 C34 H34B 110.9 . . ?
C32 C34 H34B 110.9 . . ?
H34A C34 H34B 109.0 . . ?
C34 C35 N18 104.15(15) . . ?
C34 C35 H35A 110.9 . . ?
N18 C35 H35A 110.9 . . ?
C34 C35 H35B 110.9 . . ?
N18 C35 H35B 110.9 . . ?
H35A C35 H35B 108.9 . . ?
N18 C36 H36A 109.5 . . ?
N18 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N18 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N18 C37 H37A 109.5 . . ?
N18 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N18 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O2 B1 O3 113.26(15) . . ?
O2 B1 O4 111.82(15) . . ?
O3 B1 O4 104.69(15) . . ?
O2 B1 O1 105.19(15) . . ?
O3 B1 O1 111.54(16) . . ?
O4 B1 O1 110.48(15) . . ?
O5 B2 O6 105.80(15) . . ?
O5 B2 O7 112.87(16) . . ?
O6 B2 O7 112.58(17) . . ?
O5 B2 O8 110.94(17) . . ?
O6 B2 O8 110.36(17) . . ?
O7 B2 O8 104.39(15) . . ?
C1 N1 C3 112.12(15) . . ?
C2 N2 C4 112.19(15) . . ?
C7 N5 C9 112.45(16) . . ?
C8 N6 C10 111.89(16) . . ?
C13 N9 C15 112.19(15) . . ?
C14 N10 C16 111.99(16) . . ?
C36 N18 C37 109.42(15) . . ?
C36 N18 C35 111.27(14) . . ?
C37 N18 C35 110.25(15) . . ?
C36 N18 C31 111.30(14) . . ?
C37 N18 C31 110.16(14) . . ?
C35 N18 C31 104.37(13) . . ?
C1 O1 B1 106.72(14) . . ?
C2 O2 B1 106.94(14) . . ?
C7 O3 B1 107.47(14) . . ?
C8 O4 B1 107.11(14) . . ?
C13 O5 B2 106.75(15) . . ?
C14 O6 B2 106.55(15) . . ?
C29 N17 C30 109.1(5) . . ?
C29 N17 C28 111.6(9) . . ?
C30 N17 C28 111.1(9) . . ?
C29 N17 C25 112.4(9) . . ?
C30 N17 C25 110.3(8) . . ?
C28 N17 C25 102.3(6) . . ?
C26 C25 N17 103.6(5) . . ?
C26 C25 H25A 111.0 . . ?
N17 C25 H25A 111.0 . . ?
C26 C25 H25B 111.0 . . ?
N17 C25 H25B 111.0 . . ?
H25A C25 H25B 109.0 . . ?
C25 C26 C27 107.5(3) . . ?
C25 C26 H26A 110.2 . . ?
C27 C26 H26A 110.2 . . ?
C25 C26 H26B 110.2 . . ?
C27 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
C28 C27 C26 102.9(4) . . ?
C28 C27 H27A 111.2 . . ?
C26 C27 H27A 111.2 . . ?
C28 C27 H27B 111.2 . . ?
C26 C27 H27B 111.2 . . ?
H27A C27 H27B 109.1 . . ?
N17 C28 C27 103.6(7) . . ?
N17 C28 H28A 111.0 . . ?
C27 C28 H28A 111.0 . . ?
N17 C28 H28B 111.0 . . ?
C27 C28 H28B 111.0 . . ?
H28A C28 H28B 109.0 . . ?
N17 C29 H29A 109.5 . . ?
N17 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N17 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N17 C30 H30A 109.5 . . ?
N17 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N17 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29A N17A C28A 112.0(10) . . ?
C29A N17A C25A 113.6(8) . . ?
C28A N17A C25A 104.5(7) . . ?
C29A N17A C30A 106.8(7) . . ?
C28A N17A C30A 109.7(7) . . ?
C25A N17A C30A 110.2(10) . . ?
C26A C25A N17A 105.9(8) . . ?
C26A C25A H25C 110.6 . . ?
N17A C25A H25C 110.6 . . ?
C26A C25A H25D 110.6 . . ?
N17A C25A H25D 110.6 . . ?
H25C C25A H25D 108.7 . . ?
C25A C26A C27A 107.3(4) . . ?
C25A C26A H26C 110.3 . . ?
C27A C26A H26C 110.3 . . ?
C25A C26A H26D 110.3 . . ?
C27A C26A H26D 110.3 . . ?
H26C C26A H26D 108.5 . . ?
C28A C27A C26A 103.5(3) . . ?
C28A C27A H27C 111.1 . . ?
C26A C27A H27C 111.1 . . ?
C28A C27A H27D 111.1 . . ?
C26A C27A H27D 111.1 . . ?
H27C C27A H27D 109.0 . . ?
N17A C28A C27A 103.5(6) . . ?
N17A C28A H28C 111.1 . . ?
C27A C28A H28C 111.1 . . ?
N17A C28A H28D 111.1 . . ?
C27A C28A H28D 111.1 . . ?
H28C C28A H28D 109.0 . . ?
N17A C29A H29D 109.5 . . ?
N17A C29A H29E 109.5 . . ?
H29D C29A H29E 109.5 . . ?
N17A C29A H29F 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
N17A C30A H30D 109.5 . . ?
N17A C30A H30E 109.5 . . ?
H30D C30A H30E 109.5 . . ?
N17A C30A H30F 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 109.5 . . ?
C20 N14 C22 111.7(5) . . ?
N13 C21 C22 122.9(6) . . ?
N13 C21 C23 118.2(6) . . ?
C22 C21 C23 118.4(7) . . ?
C21 C22 N14 123.8(6) . . ?
C21 C22 C24 120.7(6) . . ?
N14 C22 C24 115.5(5) . . ?
N15 C23 C21 177.9(8) . . ?
N16 C24 C22 179.1(8) . . ?
C22A N14A C20 110.7(5) . . ?
C22A C21A C23A 120.5(7) . . ?
C22A C21A N13 123.4(5) . . ?
C23A C21A N13 115.6(6) . . ?
N14A C22A C21A 124.1(5) . . ?
N14A C22A C24A 115.1(5) . . ?
C21A C22A C24A 120.8(5) . . ?
N15A C23A C21A 177.0(10) . . ?
N16A C24A C22A 177.8(8) . . ?
N8A C12A C10 173.6(9) . . ?
N8 C12 C10 173.9(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.5(3) . . . . ?
O1 C1 C2 N2 179.75(16) . . . . ?
N1 C1 C2 O2 179.63(17) . . . . ?
O1 C1 C2 O2 -0.1(2) . . . . ?
N1 C3 C4 N2 0.1(3) . . . . ?
C5 C3 C4 N2 -178.79(18) . . . . ?
N1 C3 C4 C6 179.70(17) . . . . ?
C5 C3 C4 C6 0.8(3) . . . . ?
N5 C7 C8 N6 2.2(3) . . . . ?
O3 C7 C8 N6 -177.31(17) . . . . ?
N5 C7 C8 O4 -178.77(16) . . . . ?
O3 C7 C8 O4 1.7(2) . . . . ?
N5 C9 C10 N6 1.9(3) . . . . ?
C11 C9 C10 N6 -179.81(19) . . . . ?
N5 C9 C10 C12A 173.6(10) . . . . ?
C11 C9 C10 C12A -8.2(10) . . . . ?
N5 C9 C10 C12 -166.0(9) . . . . ?
C11 C9 C10 C12 12.3(10) . . . . ?
N9 C13 C14 N10 0.5(3) . . . . ?
O5 C13 C14 N10 -177.56(17) . . . . ?
N9 C13 C14 O6 178.33(16) . . . . ?
O5 C13 C14 O6 0.2(2) . . . . ?
N9 C15 C16 N10 0.1(3) . . . . ?
C17 C15 C16 N10 179.40(17) . . . . ?
N9 C15 C16 C18 -178.04(17) . . . . ?
C17 C15 C16 C18 1.3(3) . . . . ?
B2 O7 C19 N13 -178.9(2) . . . . ?
B2 O7 C19 C20 1.4(2) . . . . ?
B2 O8 C20 N14 160.0(9) . . . . ?
B2 O8 C20 N14A -168.9(6) . . . . ?
B2 O8 C20 C19 -2.5(3) . . . . ?
N13 C19 C20 N14 17.9(9) . . . . ?
O7 C19 C20 N14 -162.3(9) . . . . ?
N13 C19 C20 O8 -179.0(2) . . . . ?
O7 C19 C20 O8 0.7(3) . . . . ?
N13 C19 C20 N14A -12.8(7) . . . . ?
O7 C19 C20 N14A 166.9(6) . . . . ?
O7 C19 N13 C21 167.3(6) . . . . ?
C20 C19 N13 C21 -13.0(7) . . . . ?
O7 C19 N13 C21A -171.2(5) . . . . ?
C20 C19 N13 C21A 8.4(6) . . . . ?
N18 C31 C32 C34 2.6(2) . . . . ?
C31 C32 C34 C35 -24.9(2) . . . . ?
C32 C34 C35 N18 38.08(19) . . . . ?
C19 O7 B2 O5 -123.34(18) . . . . ?
C19 O7 B2 O6 116.96(18) . . . . ?
C19 O7 B2 O8 -2.8(2) . . . . ?
C20 O8 B2 O5 125.1(2) . . . . ?
C20 O8 B2 O6 -118.01(19) . . . . ?
C20 O8 B2 O7 3.2(2) . . . . ?
O1 C1 N1 C3 179.50(16) . . . . ?
C2 C1 N1 C3 -0.2(3) . . . . ?
C4 C3 N1 C1 0.4(3) . . . . ?
C5 C3 N1 C1 179.28(17) . . . . ?
O2 C2 N2 C4 -179.26(16) . . . . ?
C1 C2 N2 C4 0.9(3) . . . . ?
C3 C4 N2 C2 -0.7(3) . . . . ?
C6 C4 N2 C2 179.65(16) . . . . ?
O3 C7 N5 C9 178.49(17) . . . . ?
C8 C7 N5 C9 -0.9(3) . . . . ?
C10 C9 N5 C7 -0.9(3) . . . . ?
C11 C9 N5 C7 -179.29(16) . . . . ?
O4 C8 N6 C10 179.90(17) . . . . ?
C7 C8 N6 C10 -1.2(3) . . . . ?
C9 C10 N6 C8 -0.7(3) . . . . ?
C12A C10 N6 C8 -172.3(10) . . . . ?
C12 C10 N6 C8 168.1(9) . . . . ?
O5 C13 N9 C15 177.80(16) . . . . ?
C14 C13 N9 C15 0.0(2) . . . . ?
C16 C15 N9 C13 -0.3(2) . . . . ?
C17 C15 N9 C13 -179.64(16) . . . . ?
O6 C14 N10 C16 -178.18(17) . . . . ?
C13 C14 N10 C16 -0.7(3) . . . . ?
C15 C16 N10 C14 0.4(3) . . . . ?
C18 C16 N10 C14 178.59(16) . . . . ?
C34 C35 N18 C36 -156.58(16) . . . . ?
C34 C35 N18 C37 81.83(18) . . . . ?
C34 C35 N18 C31 -36.44(18) . . . . ?
C32 C31 N18 C36 140.80(15) . . . . ?
C32 C31 N18 C37 -97.66(17) . . . . ?
C32 C31 N18 C35 20.68(18) . . . . ?
N1 C1 O1 B1 179.12(18) . . . . ?
C2 C1 O1 B1 -1.18(19) . . . . ?
O2 B1 O1 C1 1.90(19) . . . . ?
O3 B1 O1 C1 125.06(15) . . . . ?
O4 B1 O1 C1 -118.94(15) . . . . ?
N2 C2 O2 B1 -178.52(17) . . . . ?
C1 C2 O2 B1 1.3(2) . . . . ?
O3 B1 O2 C2 -124.00(16) . . . . ?
O4 B1 O2 C2 118.01(16) . . . . ?
O1 B1 O2 C2 -1.94(19) . . . . ?
N5 C7 O3 B1 -179.33(17) . . . . ?
C8 C7 O3 B1 0.15(19) . . . . ?
O2 B1 O3 C7 -123.79(16) . . . . ?
O4 B1 O3 C7 -1.73(18) . . . . ?
O1 B1 O3 C7 117.77(16) . . . . ?
N6 C8 O4 B1 176.27(19) . . . . ?
C7 C8 O4 B1 -2.8(2) . . . . ?
O2 B1 O4 C8 125.77(16) . . . . ?
O3 B1 O4 C8 2.76(18) . . . . ?
O1 B1 O4 C8 -117.44(16) . . . . ?
N9 C13 O5 B2 -174.92(18) . . . . ?
C14 C13 O5 B2 3.1(2) . . . . ?
O6 B2 O5 C13 -5.08(19) . . . . ?
O7 B2 O5 C13 -128.62(17) . . . . ?
O8 B2 O5 C13 114.62(17) . . . . ?
N10 C14 O6 B2 174.31(18) . . . . ?
C13 C14 O6 B2 -3.5(2) . . . . ?
O5 B2 O6 C14 5.21(19) . . . . ?
O7 B2 O6 C14 128.94(16) . . . . ?
O8 B2 O6 C14 -114.87(17) . . . . ?
C29 N17 C25 C26 161.7(6) . . . . ?
C30 N17 C25 C26 -76.4(7) . . . . ?
C28 N17 C25 C26 41.9(8) . . . . ?
N17 C25 C26 C27 -23.5(6) . . . . ?
C25 C26 C27 C28 -3.4(5) . . . . ?
C29 N17 C28 C27 -164.7(6) . . . . ?
C30 N17 C28 C27 73.4(8) . . . . ?
C25 N17 C28 C27 -44.3(8) . . . . ?
C26 C27 C28 N17 29.1(7) . . . . ?
C29A N17A C25A C26A 150.0(7) . . . . ?
C28A N17A C25A C26A 27.6(9) . . . . ?
C30A N17A C25A C26A -90.2(9) . . . . ?
N17A C25A C26A C27A -5.4(8) . . . . ?
C25A C26A C27A C28A -18.6(5) . . . . ?
C29A N17A C28A C27A -162.9(5) . . . . ?
C25A N17A C28A C27A -39.4(8) . . . . ?
C30A N17A C28A C27A 78.7(8) . . . . ?
C26A C27A C28A N17A 35.4(5) . . . . ?
O8 C20 N14 C22 -175.8(4) . . . . ?
C19 C20 N14 C22 -15.2(9) . . . . ?
C19 N13 C21 C22 9.1(7) . . . . ?
C19 N13 C21 C23 -179.1(4) . . . . ?
N13 C21 C22 N14 -9.3(9) . . . . ?
C23 C21 C22 N14 178.9(5) . . . . ?
N13 C21 C22 C24 171.8(7) . . . . ?
C23 C21 C22 C24 0.0(8) . . . . ?
C20 N14 C22 C21 11.8(9) . . . . ?
C20 N14 C22 C24 -169.3(7) . . . . ?
O8 C20 N14A C22A 177.3(3) . . . . ?
C19 C20 N14A C22A 12.8(7) . . . . ?
C19 N13 C21A C22A -7.2(7) . . . . ?
C19 N13 C21A C23A -178.4(4) . . . . ?
C20 N14A C22A C21A -11.4(8) . . . . ?
C20 N14A C22A C24A 166.6(6) . . . . ?
C23A C21A C22A N14A -179.5(5) . . . . ?
N13 C21A C22A N14A 9.7(9) . . . . ?
C23A C21A C22A C24A 2.6(8) . . . . ?
N13 C21A C22A C24A -168.3(7) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'acetonitrile, diethylether'
_chemical_properties_physical    ', Moisture-sensitive,Hygroscopic'
####################################################################### 
# 
# 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_AVD124
_database_code_depnum_ccdc_archive 'CCDC 1527277'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'Tris(1,2-dimethoxyethane)lithium bis(pyrazine-5,6-dicarbonitrile-2,3-diolato)borate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 B N8 O4, C12 H30 Li O6'
_chemical_formula_sum            'C24 H30 B Li N8 O10'
_chemical_formula_weight         608.31

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'
Li Li -0.0003 0.0001 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   18.9060(11)
_cell_length_b                   15.4153(9)
_cell_length_c                   21.5073(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.314(2)
_cell_angle_gamma                90
_cell_volume                     6230.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9269
_cell_measurement_theta_min      2.4693
_cell_measurement_theta_max      27.1299

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             2544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5921
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            50912
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         27.159
_diffrn_reflns_theta_full        25.000
_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             6912
_reflns_number_gt                5171
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR2014 (M. C. Burla, R. Caliandro, B. Carrozzini, G. L. Cascarano, 
C. Cuocci, C. Giacovazzo, M. Mallamo, A. Mazzone and G. Polidori, 
J. Appl. Cryst. 2015, 48, 306-309.)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (G. M. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields,
 R. Taylor, M. Towler, J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102,
53227 Bonn, Germany)
;
_computing_publication_material  
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
;
_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)+(0.0384P)²+4.4359P] 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         6912
_refine_ls_number_parameters     404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59000(7) 0.39208(8) 0.69404(6) 0.0184(3) Uani 1 1 d . . . . .
C2 C 0.61522(7) 0.32703(8) 0.73898(6) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.72225(8) 0.33596(9) 0.70579(7) 0.0217(3) Uani 1 1 d . . . . .
C4 C 0.69781(7) 0.39808(9) 0.66214(6) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.79538(8) 0.30872(10) 0.71114(7) 0.0275(3) Uani 1 1 d . . . . .
C6 C 0.74462(8) 0.43529(10) 0.62061(7) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.61368(7) 0.04914(8) 0.73567(6) 0.0183(3) Uani 1 1 d . . . . .
C8 C 0.58736(7) 0.11334(9) 0.69070(6) 0.0188(3) Uani 1 1 d . . . . .
C9 C 0.71714(7) 0.05082(9) 0.69512(6) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.69145(8) 0.11226(9) 0.65167(7) 0.0218(3) Uani 1 1 d . . . . .
C11 C 0.78828(8) 0.01730(10) 0.69469(7) 0.0256(3) Uani 1 1 d . . . . .
C12 C 0.73626(8) 0.14498(11) 0.60670(7) 0.0297(4) Uani 1 1 d . . . . .
C13 C 0.42068(11) 0.10674(11) 0.53957(9) 0.0417(4) Uani 1 1 d . . . . .
H13A H 0.4707 0.1003 0.5565 0.063 Uiso 1 1 calc R U . . .
H13B H 0.4116 0.0727 0.5010 0.063 Uiso 1 1 calc R U . . .
H13C H 0.3901 0.0859 0.5703 0.063 Uiso 1 1 calc R U . . .
C14 C 0.41959(9) 0.24776(10) 0.58117(7) 0.0284(3) Uani 1 1 d . . . . .
H14A H 0.4712 0.2484 0.5953 0.034 Uiso 1 1 calc R U . . .
H14B H 0.3944 0.2236 0.6152 0.034 Uiso 1 1 calc R U . . .
C15 C 0.39393(9) 0.33775(10) 0.56551(7) 0.0281(3) Uani 1 1 d . . . . .
H15A H 0.3415 0.3380 0.5560 0.034 Uiso 1 1 calc R U . . .
H15B H 0.4069 0.3769 0.6015 0.034 Uiso 1 1 calc R U . . .
C16 C 0.40788(10) 0.45438(10) 0.49701(8) 0.0325(4) Uani 1 1 d . . . . .
H16A H 0.3560 0.4600 0.4905 0.049 Uiso 1 1 calc R U . . .
H16B H 0.4281 0.4708 0.4586 0.049 Uiso 1 1 calc R U . . .
H16C H 0.4269 0.4925 0.5313 0.049 Uiso 1 1 calc R U . . .
C17 C 0.59472(8) 0.31110(9) 0.53302(7) 0.0242(3) Uani 1 1 d . . . . .
H17A H 0.6026 0.2755 0.5709 0.036 Uiso 1 1 calc R U . . .
H17B H 0.5668 0.3625 0.5415 0.036 Uiso 1 1 calc R U . . .
H17C H 0.6407 0.3292 0.5203 0.036 Uiso 1 1 calc R U . . .
C18 C 0.59205(8) 0.18373(10) 0.47161(8) 0.0298(4) Uani 1 1 d . . . . .
H18A H 0.5887 0.1420 0.5061 0.036 Uiso 1 1 calc R U . . .
H18B H 0.6430 0.1952 0.4682 0.036 Uiso 1 1 calc R U . . .
C19 C 0.55768(9) 0.14681(10) 0.41189(8) 0.0311(4) Uani 1 1 d . . . . .
H19A H 0.5722 0.1804 0.3761 0.037 Uiso 1 1 calc R U . . .
H19B H 0.5731 0.0859 0.4076 0.037 Uiso 1 1 calc R U . . .
C20 C 0.44683(10) 0.10600(12) 0.35947(9) 0.0440(5) Uani 1 1 d . . . . .
H20A H 0.4602 0.1313 0.3206 0.066 Uiso 1 1 calc R U . . .
H20B H 0.3954 0.1118 0.3605 0.066 Uiso 1 1 calc R U . . .
H20C H 0.4599 0.0445 0.3614 0.066 Uiso 1 1 calc R U . . .
C21 C 0.28398(9) 0.25002(14) 0.41238(9) 0.0450(5) Uani 1 1 d . . . . .
H21A H 0.2670 0.3005 0.4341 0.068 Uiso 1 1 calc R U . . .
H21B H 0.2889 0.2004 0.4410 0.068 Uiso 1 1 calc R U . . .
H21C H 0.2498 0.2358 0.3762 0.068 Uiso 1 1 calc R U . . .
C22 C 0.34696(8) 0.34168(10) 0.35030(7) 0.0277(3) Uani 1 1 d . . . . .
H22A H 0.3349 0.3949 0.3726 0.033 Uiso 1 1 calc R U . . .
H22B H 0.3096 0.3318 0.3150 0.033 Uiso 1 1 calc R U . . .
C23 C 0.41780(8) 0.35176(10) 0.32645(7) 0.0253(3) Uani 1 1 d . . . . .
H23A H 0.4274 0.3015 0.2999 0.030 Uiso 1 1 calc R U . . .
H23B H 0.4185 0.4051 0.3009 0.030 Uiso 1 1 calc R U . . .
C24 C 0.53834(8) 0.37858(10) 0.35972(7) 0.0268(3) Uani 1 1 d . . . . .
H24A H 0.5510 0.3361 0.3289 0.040 Uiso 1 1 calc R U . . .
H24B H 0.5744 0.3780 0.3961 0.040 Uiso 1 1 calc R U . . .
H24C H 0.5361 0.4365 0.3409 0.040 Uiso 1 1 calc R U . . .
Li1 Li 0.44983(13) 0.26798(15) 0.45011(11) 0.0228(5) Uani 1 1 d . . . . .
B1 B 0.5000 0.08054(14) 0.7500 0.0207(5) Uani 1 2 d S T P . .
B2 B 0.5000 0.35575(14) 0.7500 0.0214(5) Uani 1 2 d S T P . .
N1 N 0.62924(6) 0.42824(7) 0.65541(5) 0.0199(3) Uani 1 1 d . . . . .
N2 N 0.68000(6) 0.29741(7) 0.74573(6) 0.0226(3) Uani 1 1 d . . . . .
N3 N 0.85381(8) 0.28683(10) 0.71522(7) 0.0390(4) Uani 1 1 d . . . . .
N4 N 0.78081(7) 0.46466(10) 0.58677(7) 0.0363(3) Uani 1 1 d . . . . .
N5 N 0.62418(7) 0.14560(8) 0.64851(6) 0.0231(3) Uani 1 1 d . . . . .
N6 N 0.67766(6) 0.01683(8) 0.73918(5) 0.0220(3) Uani 1 1 d . . . . .
N7 N 0.84479(7) -0.00899(9) 0.69354(7) 0.0347(3) Uani 1 1 d . . . . .
N8 N 0.77217(8) 0.17106(11) 0.57155(7) 0.0468(4) Uani 1 1 d . . . . .
O1 O 0.52234(5) 0.40945(6) 0.69827(4) 0.0214(2) Uani 1 1 d . . . . .
O2 O 0.56339(5) 0.30257(6) 0.77158(5) 0.0224(2) Uani 1 1 d . . . . .
O3 O 0.52100(5) 0.13337(6) 0.69756(4) 0.0225(2) Uani 1 1 d . . . . .
O4 O 0.56363(5) 0.02717(6) 0.77092(4) 0.0221(2) Uani 1 1 d . . . . .
O5 O 0.42632(5) 0.36683(6) 0.51245(5) 0.0236(2) Uani 1 1 d . . . . .
O6 O 0.40575(6) 0.19601(7) 0.52620(5) 0.0298(3) Uani 1 1 d . . . . .
O7 O 0.35084(5) 0.26927(7) 0.39183(5) 0.0278(2) Uani 1 1 d . . . . .
O8 O 0.47057(5) 0.35688(6) 0.37897(4) 0.0225(2) Uani 1 1 d . . . . .
O9 O 0.48316(6) 0.15019(7) 0.41157(5) 0.0315(3) Uani 1 1 d . . . . .
O10 O 0.55707(5) 0.26178(6) 0.48415(5) 0.0249(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.2989(18) . ?
C1 O1 1.3197(17) . ?
C1 C2 1.4373(19) . ?
C2 N2 1.3001(18) . ?
C2 O2 1.3210(17) . ?
C3 N2 1.3711(19) . ?
C3 C4 1.384(2) . ?
C3 C5 1.437(2) . ?
C4 N1 1.3698(18) . ?
C4 C6 1.443(2) . ?
C5 N3 1.149(2) . ?
C6 N4 1.146(2) . ?
C7 N6 1.3025(18) . ?
C7 O4 1.3202(17) . ?
C7 C8 1.4340(19) . ?
C8 N5 1.3016(18) . ?
C8 O3 1.3159(17) . ?
C9 N6 1.3730(18) . ?
C9 C10 1.381(2) . ?
C9 C11 1.442(2) . ?
C10 N5 1.3665(19) . ?
C10 C12 1.445(2) . ?
C11 N7 1.145(2) . ?
C12 N8 1.143(2) . ?
C13 O6 1.428(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O6 1.4264(18) . ?
C14 C15 1.496(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O5 1.4256(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O5 1.4240(17) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O10 1.4231(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O10 1.4131(18) . ?
C18 C19 1.487(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O9 1.409(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O9 1.4220(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O7 1.416(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O7 1.4264(18) . ?
C22 C23 1.494(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O8 1.4247(17) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O8 1.4288(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
Li1 O10 2.081(3) . ?
Li1 O5 2.109(3) . ?
Li1 O9 2.120(3) . ?
Li1 O8 2.122(3) . ?
Li1 O7 2.135(3) . ?
Li1 O6 2.214(3) . ?
B1 O3 1.4803(15) 2_656 ?
B1 O3 1.4803(15) . ?
B1 O4 1.4858(15) 2_656 ?
B1 O4 1.4858(15) . ?
B2 O2 1.4836(15) . ?
B2 O2 1.4837(15) 2_656 ?
B2 O1 1.4849(16) . ?
B2 O1 1.4850(16) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 O1 125.67(12) . . ?
N1 C1 C2 123.99(13) . . ?
O1 C1 C2 110.34(12) . . ?
N2 C2 O2 125.82(12) . . ?
N2 C2 C1 123.97(13) . . ?
O2 C2 C1 110.21(12) . . ?
N2 C3 C4 123.41(13) . . ?
N2 C3 C5 116.41(13) . . ?
C4 C3 C5 120.19(14) . . ?
N1 C4 C3 123.22(13) . . ?
N1 C4 C6 115.93(12) . . ?
C3 C4 C6 120.85(13) . . ?
N3 C5 C3 179.8(2) . . ?
N4 C6 C4 178.75(17) . . ?
N6 C7 O4 126.03(12) . . ?
N6 C7 C8 123.66(13) . . ?
O4 C7 C8 110.29(12) . . ?
N5 C8 O3 125.32(13) . . ?
N5 C8 C7 124.14(13) . . ?
O3 C8 C7 110.53(12) . . ?
N6 C9 C10 123.47(13) . . ?
N6 C9 C11 116.49(12) . . ?
C10 C9 C11 120.02(13) . . ?
N5 C10 C9 123.20(13) . . ?
N5 C10 C12 116.53(13) . . ?
C9 C10 C12 120.27(13) . . ?
N7 C11 C9 179.09(16) . . ?
N8 C12 C10 179.4(2) . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 C15 107.87(12) . . ?
O6 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O6 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O5 C15 C14 108.34(12) . . ?
O5 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O10 C17 H17A 109.5 . . ?
O10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C18 C19 108.74(12) . . ?
O10 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O10 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O9 C19 C18 109.37(13) . . ?
O9 C19 H19A 109.8 . . ?
C18 C19 H19A 109.8 . . ?
O9 C19 H19B 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
O9 C20 H20A 109.5 . . ?
O9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 C23 108.06(12) . . ?
O7 C22 H22A 110.1 . . ?
C23 C22 H22A 110.1 . . ?
O7 C22 H22B 110.1 . . ?
C23 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
O8 C23 C22 108.04(12) . . ?
O8 C23 H23A 110.1 . . ?
C22 C23 H23A 110.1 . . ?
O8 C23 H23B 110.1 . . ?
C22 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O10 Li1 O5 94.30(10) . . ?
O10 Li1 O9 77.19(9) . . ?
O5 Li1 O9 163.67(13) . . ?
O10 Li1 O8 91.90(10) . . ?
O5 Li1 O8 93.46(10) . . ?
O9 Li1 O8 100.64(11) . . ?
O10 Li1 O7 164.65(13) . . ?
O5 Li1 O7 97.71(11) . . ?
O9 Li1 O7 93.29(10) . . ?
O8 Li1 O7 77.90(9) . . ?
O10 Li1 O6 98.53(10) . . ?
O5 Li1 O6 76.67(9) . . ?
O9 Li1 O6 90.68(10) . . ?
O8 Li1 O6 166.08(13) . . ?
O7 Li1 O6 93.54(10) . . ?
O3 B1 O3 113.25(16) 2_656 . ?
O3 B1 O4 105.03(5) 2_656 2_656 ?
O3 B1 O4 110.49(5) . 2_656 ?
O3 B1 O4 110.49(5) 2_656 . ?
O3 B1 O4 105.03(5) . . ?
O4 B1 O4 112.75(16) 2_656 . ?
O2 B2 O2 112.91(16) . 2_656 ?
O2 B2 O1 104.82(5) . . ?
O2 B2 O1 111.11(5) 2_656 . ?
O2 B2 O1 111.11(5) . 2_656 ?
O2 B2 O1 104.83(5) 2_656 2_656 ?
O1 B2 O1 112.23(16) . 2_656 ?
C1 N1 C4 112.79(12) . . ?
C2 N2 C3 112.61(12) . . ?
C8 N5 C10 112.83(12) . . ?
C7 N6 C9 112.69(12) . . ?
C1 O1 B2 107.23(9) . . ?
C2 O2 B2 107.29(9) . . ?
C8 O3 B1 107.17(9) . . ?
C7 O4 B1 106.96(9) . . ?
C16 O5 C15 111.66(11) . . ?
C16 O5 Li1 126.86(11) . . ?
C15 O5 Li1 114.89(11) . . ?
C14 O6 C13 110.97(12) . . ?
C14 O6 Li1 106.42(10) . . ?
C13 O6 Li1 123.35(12) . . ?
C21 O7 C22 111.92(13) . . ?
C21 O7 Li1 124.74(11) . . ?
C22 O7 Li1 110.87(11) . . ?
C23 O8 C24 110.81(11) . . ?
C23 O8 Li1 111.53(10) . . ?
C24 O8 Li1 127.07(11) . . ?
C19 O9 C20 112.47(13) . . ?
C19 O9 Li1 111.69(11) . . ?
C20 O9 Li1 125.43(12) . . ?
C18 O10 C17 112.90(11) . . ?
C18 O10 Li1 115.50(11) . . ?
C17 O10 Li1 128.63(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
N1 C1 C2 N2 0.0(2) . . . . ?
O1 C1 C2 N2 -179.64(12) . . . . ?
N1 C1 C2 O2 -179.99(12) . . . . ?
O1 C1 C2 O2 0.41(16) . . . . ?
N2 C3 C4 N1 1.3(2) . . . . ?
C5 C3 C4 N1 -178.64(13) . . . . ?
N2 C3 C4 C6 -178.95(13) . . . . ?
C5 C3 C4 C6 1.2(2) . . . . ?
N6 C7 C8 N5 0.5(2) . . . . ?
O4 C7 C8 N5 -178.05(13) . . . . ?
N6 C7 C8 O3 179.38(12) . . . . ?
O4 C7 C8 O3 0.83(16) . . . . ?
N6 C9 C10 N5 0.3(2) . . . . ?
C11 C9 C10 N5 178.66(13) . . . . ?
N6 C9 C10 C12 -179.99(14) . . . . ?
C11 C9 C10 C12 -1.7(2) . . . . ?
O6 C14 C15 O5 -54.20(16) . . . . ?
O10 C18 C19 O9 -45.53(18) . . . . ?
O7 C22 C23 O8 -53.92(15) . . . . ?
O1 C1 N1 C4 179.25(12) . . . . ?
C2 C1 N1 C4 -0.29(19) . . . . ?
C3 C4 N1 C1 -0.29(19) . . . . ?
C6 C4 N1 C1 179.90(12) . . . . ?
O2 C2 N2 C3 -179.17(13) . . . . ?
C1 C2 N2 C3 0.89(19) . . . . ?
C4 C3 N2 C2 -1.5(2) . . . . ?
C5 C3 N2 C2 178.43(13) . . . . ?
O3 C8 N5 C10 -179.18(12) . . . . ?
C7 C8 N5 C10 -0.5(2) . . . . ?
C9 C10 N5 C8 0.1(2) . . . . ?
C12 C10 N5 C8 -179.61(13) . . . . ?
O4 C7 N6 C9 178.26(12) . . . . ?
C8 C7 N6 C9 -0.07(19) . . . . ?
C10 C9 N6 C7 -0.3(2) . . . . ?
C11 C9 N6 C7 -178.69(12) . . . . ?
N1 C1 O1 B2 -177.83(13) . . . . ?
C2 C1 O1 B2 1.76(14) . . . . ?
O2 B2 O1 C1 -3.06(14) . . . . ?
O2 B2 O1 C1 -125.33(11) 2_656 . . . ?
O1 B2 O1 C1 117.65(9) 2_656 . . . ?
N2 C2 O2 B2 177.68(13) . . . . ?
C1 C2 O2 B2 -2.38(14) . . . . ?
O2 B2 O2 C2 124.40(10) 2_656 . . . ?
O1 B2 O2 C2 3.30(14) . . . . ?
O1 B2 O2 C2 -118.15(12) 2_656 . . . ?
N5 C8 O3 B1 178.92(13) . . . . ?
C7 C8 O3 B1 0.05(15) . . . . ?
O3 B1 O3 C8 119.85(10) 2_656 . . . ?
O4 B1 O3 C8 -122.65(11) 2_656 . . . ?
O4 B1 O3 C8 -0.80(14) . . . . ?
N6 C7 O4 B1 -179.81(13) . . . . ?
C8 C7 O4 B1 -1.30(14) . . . . ?
O3 B1 O4 C7 -121.16(11) 2_656 . . . ?
O3 B1 O4 C7 1.29(14) . . . . ?
O4 B1 O4 C7 121.66(10) 2_656 . . . ?
C14 C15 O5 C16 -176.34(12) . . . . ?
C14 C15 O5 Li1 30.06(16) . . . . ?
C15 C14 O6 C13 -172.72(13) . . . . ?
C15 C14 O6 Li1 50.67(15) . . . . ?
C23 C22 O7 C21 -174.67(13) . . . . ?
C23 C22 O7 Li1 41.14(15) . . . . ?
C22 C23 O8 C24 -171.96(12) . . . . ?
C22 C23 O8 Li1 40.57(15) . . . . ?
C18 C19 O9 C20 -172.48(14) . . . . ?
C18 C19 O9 Li1 40.41(17) . . . . ?
C19 C18 O10 C17 -167.85(13) . . . . ?
C19 C18 O10 Li1 29.92(17) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
