# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1043674'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013



_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'B5 H4 O10, C4 H10 N'
_chemical_formula_sum            'C4 H14 B5 N O10'
_chemical_formula_weight         290.21

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                   8.8681(5)
_cell_length_b                   8.8820(6)
_cell_length_c                   9.6340(6)
_cell_angle_alpha                77.006(5)
_cell_angle_beta                 75.896(5)
_cell_angle_gamma                64.320(5)
_cell_volume                     657.07(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5441
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;

_exptl_special_details           
;
Rigaku CrystalClear-SM Expert 2.0 r13
;

_diffrn_ambient_temperature      120(2)
_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source                   'Sealed X-Ray tube'
_diffrn_source_target            Mo
_diffrn_source_size              '12mm x 0.4 mm long fine-focus'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    '0.3 mm'

_diffrn_detector                 'Image plate'
_diffrn_detector_type            'Rigaku Curved Fujifilm '
_diffrn_detector_area_resol_mean 10

_diffrn_measurement_device       'three-circle quarter χ goniometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'profile data from oscillation ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            7117
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2998
_reflns_number_gt                2220
_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       
;
Rigaku CrystalClear-SM Expert 2.0 r13
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r13
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r13
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (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)+(0.0558P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_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
B1 B 0.1184(2) 0.6460(2) 0.1918(2) 0.0145(4) Uani 1 1 d . . . . .
B2 B 0.4191(2) 0.4462(2) 0.1665(2) 0.0160(4) Uani 1 1 d . . . . .
B3 B 0.2345(2) 0.4101(2) 0.0460(2) 0.0180(4) Uani 1 1 d . . . . .
B4 B -0.1245(2) 0.9254(2) 0.1849(2) 0.0177(4) Uani 1 1 d . . . . .
B5 B -0.1350(2) 0.7147(2) 0.3860(2) 0.0182(4) Uani 1 1 d . . . . .
O1 O 0.29558(14) 0.59804(14) 0.19960(13) 0.0164(3) Uani 1 1 d . . . . .
O2 O 0.39076(15) 0.34995(15) 0.08839(13) 0.0196(3) Uani 1 1 d . . . . .
O3 O 0.10310(14) 0.54883(15) 0.09486(13) 0.0178(3) Uani 1 1 d . . . . .
O4 O 0.03921(14) 0.82713(14) 0.13500(12) 0.0158(3) Uani 1 1 d . . . . .
O5 O -0.21629(15) 0.86887(16) 0.30590(13) 0.0229(3) Uani 1 1 d . . . . .
O6 O 0.02828(14) 0.61394(14) 0.33767(12) 0.0176(3) Uani 1 1 d . . . . .
O7 O 0.57183(15) 0.39378(15) 0.20740(15) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.6346 0.2970 0.1849 0.034 Uiso 1 1 calc R U . . .
O8 O 0.21855(15) 0.32362(16) -0.04587(15) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.1183 0.3674 -0.0618 0.036 Uiso 1 1 calc R U . . .
O9 O -0.20437(16) 1.08505(16) 0.11986(14) 0.0247(3) Uani 1 1 d . . . . .
H9 H -0.1404 1.1052 0.0449 0.037 Uiso 1 1 calc R U . . .
O10 O -0.22393(16) 0.67293(17) 0.51199(15) 0.0295(3) Uani 1 1 d . . . . .
H10 H -0.1632 0.5785 0.5519 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3716(3) 0.9676(3) 0.1847(3) 0.0382(5) Uani 1 1 d . . . . .
H11A H 0.3402 0.9772 0.0902 0.046 Uiso 1 1 calc R U . . .
H11B H 0.4456 1.0287 0.1719 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2140(3) 1.0377(3) 0.2963(4) 0.0537(7) Uani 1 1 d . . . . .
H12A H 0.2090 1.1398 0.3260 0.064 Uiso 1 1 calc R U . . .
H12B H 0.1105 1.0682 0.2559 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2269(4) 0.9023(4) 0.4225(3) 0.0575(8) Uani 1 1 d . . . . .
H13A H 0.1538 0.8440 0.4220 0.069 Uiso 1 1 calc R U . . .
H13B H 0.1921 0.9500 0.5144 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4138(3) 0.7806(4) 0.4045(3) 0.0511(7) Uani 1 1 d . . . . .
H14A H 0.4825 0.8197 0.4430 0.061 Uiso 1 1 calc R U . . .
H14B H 0.4285 0.6653 0.4525 0.061 Uiso 1 1 calc R U . . .
N11 N 0.45861(19) 0.7876(2) 0.24412(18) 0.0257(4) Uani 1 1 d . . . . .
H11C H 0.5830 0.7482 0.2132 0.031 Uiso 1 1 calc R U . . .
H11D H 0.4188 0.7157 0.2105 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.456(2) . ?
B1 O3 1.470(2) . ?
B1 O6 1.471(2) . ?
B1 O4 1.481(2) . ?
B2 O7 1.356(2) . ?
B2 O1 1.365(2) . ?
B2 O2 1.388(2) . ?
B3 O3 1.359(2) . ?
B3 O8 1.362(2) . ?
B3 O2 1.381(2) . ?
B4 O9 1.360(2) . ?
B4 O4 1.361(2) . ?
B4 O5 1.379(2) . ?
B5 O10 1.347(2) . ?
B5 O6 1.360(2) . ?
B5 O5 1.390(2) . ?
O7 H7 0.8400 . ?
O8 H8 0.8400 . ?
O9 H9 0.8400 . ?
O10 H10 0.8400 . ?
C11 N11 1.488(3) . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.493(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N11 1.493(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N11 H11C 0.9900 . ?
N11 H11D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O3 110.89(13) . . ?
O1 B1 O6 108.83(13) . . ?
O3 B1 O6 109.47(13) . . ?
O1 B1 O4 110.27(13) . . ?
O3 B1 O4 107.86(13) . . ?
O6 B1 O4 109.51(13) . . ?
O7 B2 O1 118.60(16) . . ?
O7 B2 O2 120.66(15) . . ?
O1 B2 O2 120.70(15) . . ?
O3 B3 O8 121.86(16) . . ?
O3 B3 O2 121.20(16) . . ?
O8 B3 O2 116.95(15) . . ?
O9 B4 O4 121.73(16) . . ?
O9 B4 O5 116.84(15) . . ?
O4 B4 O5 121.42(15) . . ?
O10 B5 O6 122.69(16) . . ?
O10 B5 O5 117.18(15) . . ?
O6 B5 O5 120.12(16) . . ?
B2 O1 B1 122.10(13) . . ?
B3 O2 B2 118.68(14) . . ?
B3 O3 B1 122.78(14) . . ?
B4 O4 B1 121.75(13) . . ?
B4 O5 B5 119.14(14) . . ?
B5 O6 B1 123.08(13) . . ?
B2 O7 H7 109.5 . . ?
B3 O8 H8 109.5 . . ?
B4 O9 H9 109.5 . . ?
B5 O10 H10 109.5 . . ?
N11 C11 C12 104.9(2) . . ?
N11 C11 H11A 110.8 . . ?
C12 C11 H11A 110.8 . . ?
N11 C11 H11B 110.8 . . ?
C12 C11 H11B 110.8 . . ?
H11A C11 H11B 108.8 . . ?
C13 C12 C11 106.7(2) . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 C14 105.2(2) . . ?
C12 C13 H13A 110.7 . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
C14 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
N11 C14 C13 101.4(2) . . ?
N11 C14 H14A 111.5 . . ?
C13 C14 H14A 111.5 . . ?
N11 C14 H14B 111.5 . . ?
C13 C14 H14B 111.5 . . ?
H14A C14 H14B 109.3 . . ?
C11 N11 C14 105.77(19) . . ?
C11 N11 H11C 110.6 . . ?
C14 N11 H11C 110.6 . . ?
C11 N11 H11D 110.6 . . ?
C14 N11 H11D 110.6 . . ?
H11C N11 H11D 108.7 . . ?

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
O7 B2 O1 B1 -164.92(15) . . . . ?
O2 B2 O1 B1 17.2(2) . . . . ?
O3 B1 O1 B2 -22.2(2) . . . . ?
O6 B1 O1 B2 98.26(17) . . . . ?
O4 B1 O1 B2 -141.60(15) . . . . ?
O3 B3 O2 B2 -8.6(2) . . . . ?
O8 B3 O2 B2 171.76(15) . . . . ?
O7 B2 O2 B3 -178.46(16) . . . . ?
O1 B2 O2 B3 -0.6(2) . . . . ?
O8 B3 O3 B1 -178.81(15) . . . . ?
O2 B3 O3 B1 1.6(3) . . . . ?
O1 B1 O3 B3 13.0(2) . . . . ?
O6 B1 O3 B3 -107.14(17) . . . . ?
O4 B1 O3 B3 133.78(15) . . . . ?
O9 B4 O4 B1 -170.94(16) . . . . ?
O5 B4 O4 B1 10.4(3) . . . . ?
O1 B1 O4 B4 -143.35(15) . . . . ?
O3 B1 O4 B4 95.43(17) . . . . ?
O6 B1 O4 B4 -23.6(2) . . . . ?
O9 B4 O5 B5 -172.64(16) . . . . ?
O4 B4 O5 B5 6.1(3) . . . . ?
O10 B5 O5 B4 172.70(17) . . . . ?
O6 B5 O5 B4 -6.3(3) . . . . ?
O10 B5 O6 B1 170.98(16) . . . . ?
O5 B5 O6 B1 -10.0(3) . . . . ?
O1 B1 O6 B5 144.22(15) . . . . ?
O3 B1 O6 B5 -94.44(18) . . . . ?
O4 B1 O6 B5 23.6(2) . . . . ?
N11 C11 C12 C13 6.4(3) . . . . ?
C11 C12 C13 C14 18.1(3) . . . . ?
C12 C13 C14 N11 -35.5(3) . . . . ?
C12 C11 N11 C14 -29.4(2) . . . . ?
C13 C14 N11 C11 40.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O9 0.84 1.93 2.7708(18) 173.8 1_645
O8 H8 O3 0.84 1.86 2.6939(17) 176.5 2_565
O9 H9 O4 0.84 1.85 2.6755(17) 168.6 2_575
O10 H10 O6 0.84 1.87 2.7081(17) 171.2 2_566
N11 H11C O8 0.99 2.05 2.924(2) 145.9 2_665
N11 H11D O1 0.99 1.84 2.801(2) 162.1 .

_refine_diff_density_max         0.782
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1043675'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'B5 H4 O10, C5 H12 N, 0.5(C3 H6 O)'
_chemical_formula_sum            'C6.50 H19 B5 N O10.50'
_chemical_formula_weight         333.28

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                   14.496(3)
_cell_length_b                   11.640(2)
_cell_length_c                   18.255(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.200(4)
_cell_angle_gamma                90
_cell_volume                     2942.5(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3991
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            13841
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3340
_reflns_number_gt                3157
_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       
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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)+(0.0497P)²+1.4935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3340
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
B1 B 0.22541(7) 0.10748(9) 0.30136(6) 0.0112(2) Uani 1 1 d . . . . .
B2 B 0.26901(7) 0.21362(9) 0.19719(6) 0.0119(2) Uani 1 1 d . . . . .
B3 B 0.26754(7) 0.00893(9) 0.19419(6) 0.0123(2) Uani 1 1 d . . . . .
B4 B 0.09150(8) 0.07837(9) 0.35904(6) 0.0127(2) Uani 1 1 d . . . . .
B5 B 0.25277(8) 0.09420(9) 0.44264(6) 0.0130(2) Uani 1 1 d . . . . .
O1 O 0.24347(5) 0.21307(6) 0.26364(4) 0.01204(15) Uani 1 1 d . . . . .
O2 O 0.27929(5) 0.11197(6) 0.16097(4) 0.01425(16) Uani 1 1 d . . . . .
O3 O 0.24840(5) 0.00475(6) 0.26272(4) 0.01233(15) Uani 1 1 d . . . . .
O4 O 0.12260(5) 0.10103(6) 0.29696(4) 0.01227(15) Uani 1 1 d . . . . .
O5 O 0.15602(5) 0.07285(6) 0.43214(4) 0.01470(16) Uani 1 1 d . . . . .
O6 O 0.28676(5) 0.11042(6) 0.38122(4) 0.01272(15) Uani 1 1 d . . . . .
O7 O 0.28643(5) 0.31281(6) 0.16469(4) 0.01492(16) Uani 1 1 d . . . . .
H7 H 0.2726 0.3689 0.1884 0.022 Uiso 1 1 calc R U . . .
O8 O 0.27537(5) -0.08942(6) 0.15526(4) 0.01534(16) Uani 1 1 d . . . . .
H8 H 0.2664 -0.1468 0.1802 0.023 Uiso 1 1 calc R U . . .
O9 O -0.00350(5) 0.06166(6) 0.35222(4) 0.01660(16) Uani 1 1 d . . . . .
H9 H -0.0362 0.0689 0.3061 0.025 Uiso 1 1 calc R U . . .
O10 O 0.31729(5) 0.10129(6) 0.51370(4) 0.01771(16) Uani 1 1 d . . . . .
H10 H 0.2884 0.0924 0.5470 0.027 Uiso 1 1 calc R U . . .
C1 C 0.53617(8) 0.13395(9) 0.44343(7) 0.0242(2) Uani 1 1 d . . . . .
H1A H 0.5512 0.0879 0.4028 0.029 Uiso 1 1 calc R U . . .
H1B H 0.5121 0.0820 0.4766 0.029 Uiso 1 1 calc R U . . .
C2 C 0.62440(8) 0.19944(12) 0.49001(7) 0.0298(3) Uani 1 1 d . . . . .
H2A H 0.6697 0.2124 0.4595 0.036 Uiso 1 1 calc R U . . .
H2B H 0.6584 0.1562 0.5369 0.036 Uiso 1 1 calc R U . . .
C3 C 0.58691(8) 0.31375(10) 0.51083(7) 0.0271(2) Uani 1 1 d . . . . .
H3A H 0.6009 0.3207 0.5671 0.033 Uiso 1 1 calc R U . . .
H3B H 0.6178 0.3788 0.4922 0.033 Uiso 1 1 calc R U . . .
C4 C 0.47824(8) 0.31363(10) 0.47190(6) 0.0237(2) Uani 1 1 d . . . . .
H4A H 0.4429 0.2920 0.5087 0.028 Uiso 1 1 calc R U . . .
H4B H 0.4559 0.3903 0.4504 0.028 Uiso 1 1 calc R U . . .
C5 C 0.47669(8) 0.27382(9) 0.33779(6) 0.0196(2) Uani 1 1 d . . . . .
H5A H 0.5428 0.3029 0.3484 0.029 Uiso 1 1 calc R U . . .
H5B H 0.4309 0.3368 0.3193 0.029 Uiso 1 1 calc R U . . .
H5C H 0.4654 0.2136 0.2986 0.029 Uiso 1 1 calc R U . . .
N1 N 0.46312(6) 0.22559(7) 0.40911(5) 0.01541(18) Uani 1 1 d . . . . .
H1 H 0.3966 0.1928 0.3977 0.018 Uiso 1 1 calc R U . . .
C11 C 0.0000 0.42602(12) 0.2500 0.0200(3) Uani 1 2 d S T P . .
C12 C 0.02464(8) 0.35947(10) 0.18793(7) 0.0246(2) Uani 1 1 d . . . . .
H12A H -0.0350 0.3347 0.1497 0.037 Uiso 1 1 calc R U . . .
H12B H 0.0631 0.2920 0.2103 0.037 Uiso 1 1 calc R U . . .
H12C H 0.0619 0.4083 0.1633 0.037 Uiso 1 1 calc R U . . .
O11 O 0.0000 0.53092(9) 0.2500 0.0288(3) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O6 1.4666(12) . ?
B1 O1 1.4696(12) . ?
B1 O4 1.4704(12) . ?
B1 O3 1.4756(12) . ?
B2 O7 1.3555(12) . ?
B2 O1 1.3689(12) . ?
B2 O2 1.3848(12) . ?
B3 O3 1.3600(12) . ?
B3 O8 1.3698(12) . ?
B3 O2 1.3772(12) . ?
B4 O9 1.3596(13) . ?
B4 O4 1.3636(12) . ?
B4 O5 1.3862(13) . ?
B5 O10 1.3590(13) . ?
B5 O6 1.3647(13) . ?
B5 O5 1.3808(13) . ?
O7 H7 0.8400 . ?
O8 H8 0.8400 . ?
O9 H9 0.8400 . ?
O10 H10 0.8400 . ?
C1 N1 1.5031(13) . ?
C1 C2 1.5154(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5272(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5247(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.5046(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.4833(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N1 H1 1.0000 . ?
C11 O11 1.2211(18) . ?
C11 C12 1.5003(14) . ?
C11 C12 1.5003(14) 2 ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O6 B1 O1 107.85(7) . . ?
O6 B1 O4 111.25(8) . . ?
O1 B1 O4 109.58(7) . . ?
O6 B1 O3 109.74(7) . . ?
O1 B1 O3 110.92(8) . . ?
O4 B1 O3 107.52(7) . . ?
O7 B2 O1 121.74(8) . . ?
O7 B2 O2 117.29(8) . . ?
O1 B2 O2 120.97(8) . . ?
O3 B3 O8 121.20(9) . . ?
O3 B3 O2 121.45(8) . . ?
O8 B3 O2 117.35(8) . . ?
O9 B4 O4 121.77(9) . . ?
O9 B4 O5 117.28(9) . . ?
O4 B4 O5 120.95(9) . . ?
O10 B5 O6 117.53(9) . . ?
O10 B5 O5 121.83(9) . . ?
O6 B5 O5 120.64(9) . . ?
B2 O1 B1 123.46(7) . . ?
B3 O2 B2 119.28(8) . . ?
B3 O3 B1 123.16(7) . . ?
B4 O4 B1 122.91(8) . . ?
B5 O5 B4 119.59(8) . . ?
B5 O6 B1 123.60(8) . . ?
B2 O7 H7 109.5 . . ?
B3 O8 H8 109.5 . . ?
B4 O9 H9 109.5 . . ?
B5 O10 H10 109.5 . . ?
N1 C1 C2 104.51(9) . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C1 C2 C3 105.93(9) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 106.13(9) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C3 104.68(8) . . ?
N1 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
N1 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C5 N1 C1 112.00(8) . . ?
C5 N1 C4 112.56(8) . . ?
C1 N1 C4 103.87(8) . . ?
C5 N1 H1 109.4 . . ?
C1 N1 H1 109.4 . . ?
C4 N1 H1 109.4 . . ?
O11 C11 C12 121.08(7) . . ?
O11 C11 C12 121.08(7) . 2 ?
C12 C11 C12 117.83(13) . 2 ?
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 . . ?

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
O7 B2 O1 B1 -179.03(8) . . . . ?
O2 B2 O1 B1 0.12(14) . . . . ?
O6 B1 O1 B2 126.14(9) . . . . ?
O4 B1 O1 B2 -112.62(9) . . . . ?
O3 B1 O1 B2 5.94(12) . . . . ?
O3 B3 O2 B2 -1.64(14) . . . . ?
O8 B3 O2 B2 178.02(8) . . . . ?
O7 B2 O2 B3 176.44(8) . . . . ?
O1 B2 O2 B3 -2.75(14) . . . . ?
O8 B3 O3 B1 -170.88(8) . . . . ?
O2 B3 O3 B1 8.77(14) . . . . ?
O6 B1 O3 B3 -129.40(9) . . . . ?
O1 B1 O3 B3 -10.33(12) . . . . ?
O4 B1 O3 B3 109.47(9) . . . . ?
O9 B4 O4 B1 -173.41(8) . . . . ?
O5 B4 O4 B1 7.39(13) . . . . ?
O6 B1 O4 B4 -11.70(12) . . . . ?
O1 B1 O4 B4 -130.87(9) . . . . ?
O3 B1 O4 B4 108.48(9) . . . . ?
O10 B5 O5 B4 173.26(9) . . . . ?
O6 B5 O5 B4 -5.93(14) . . . . ?
O9 B4 O5 B5 -177.16(8) . . . . ?
O4 B4 O5 B5 2.08(14) . . . . ?
O10 B5 O6 B1 -178.80(8) . . . . ?
O5 B5 O6 B1 0.42(14) . . . . ?
O1 B1 O6 B5 128.05(9) . . . . ?
O4 B1 O6 B5 7.85(12) . . . . ?
O3 B1 O6 B5 -111.01(9) . . . . ?
N1 C1 C2 C3 25.25(12) . . . . ?
C1 C2 C3 C4 -2.96(13) . . . . ?
C2 C3 C4 N1 -20.39(12) . . . . ?
C2 C1 N1 C5 83.56(11) . . . . ?
C2 C1 N1 C4 -38.18(11) . . . . ?
C3 C4 N1 C5 -85.16(10) . . . . ?
C3 C4 N1 C1 36.20(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O3 0.84 1.88 2.7199(10) 173.4 4
O8 H8 O1 0.84 1.95 2.7912(10) 174.4 4_545
O9 H9 O4 0.84 1.96 2.7975(11) 172.4 2
O10 H10 O8 0.84 2.04 2.8275(11) 155.7 6_556
N1 H1 O6 1.00 1.81 2.7968(11) 170.3 .

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1043676'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012



_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'B5 H4 O10, C6 H14 N'
_chemical_formula_sum            'C6 H18 B5 N O10'
_chemical_formula_weight         318.26

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

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

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

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

_cell_length_a                   9.166(4)
_cell_length_b                   9.380(5)
_cell_length_c                   9.883(4)
_cell_angle_alpha                64.88(2)
_cell_angle_beta                 75.49(3)
_cell_angle_gamma                84.73(4)
_cell_volume                     744.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2954
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      29.4

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_process_details   
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            9366
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.081
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3355
_reflns_number_gt                2919
_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       
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 3.1 b18
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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)+(0.0948P)²+0.0624P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3355
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
B1 B 0.69382(18) 0.38952(19) 0.24829(19) 0.0172(3) Uani 1 1 d . . . . .
B2 B 0.88750(19) 0.6083(2) 0.12982(19) 0.0190(3) Uani 1 1 d . . . . .
B3 B 0.67945(18) 0.61041(19) 0.33085(19) 0.0173(3) Uani 1 1 d . . . . .
B4 B 0.66937(18) 0.1029(2) 0.3283(2) 0.0189(3) Uani 1 1 d . . . . .
B5 B 0.53076(18) 0.2760(2) 0.1489(2) 0.0194(4) Uani 1 1 d . . . . .
O1 O 0.83725(11) 0.46911(12) 0.14460(12) 0.0194(3) Uani 1 1 d . . . . .
O2 O 0.80748(12) 0.68311(12) 0.21966(13) 0.0214(3) Uani 1 1 d . . . . .
O3 O 0.62789(11) 0.46935(12) 0.35124(12) 0.0182(3) Uani 1 1 d . . . . .
O4 O 0.72301(11) 0.22635(12) 0.34084(12) 0.0185(3) Uani 1 1 d . . . . .
O5 O 0.57085(12) 0.12458(12) 0.23555(13) 0.0225(3) Uani 1 1 d . . . . .
O6 O 0.58805(11) 0.40312(12) 0.15289(12) 0.0189(3) Uani 1 1 d . . . . .
O7 O 1.01774(12) 0.68017(13) 0.02972(14) 0.0255(3) Uani 1 1 d . . . . .
H7 H 1.0564 0.6278 -0.0210 0.038 Uiso 1 1 calc R U . . .
O8 O 0.60989(12) 0.68631(12) 0.42036(13) 0.0210(3) Uani 1 1 d . . . . .
H8 H 0.5371 0.6309 0.4877 0.032 Uiso 1 1 calc R U . . .
O9 O 0.71705(13) -0.04396(12) 0.40904(13) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.6754 -0.1105 0.3943 0.035 Uiso 1 1 calc R U . . .
O10 O 0.43505(13) 0.29164(13) 0.05818(14) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.4269 0.3875 0.0022 0.040 Uiso 1 1 calc R U . . .
C1 C 0.0736(2) 0.7738(2) 0.4036(2) 0.0302(4) Uani 1 1 d . . . . .
H1A H -0.0363 0.7789 0.4107 0.036 Uiso 1 1 calc R U . . .
H1B H 0.0916 0.7643 0.5017 0.036 Uiso 1 1 calc R U . . .
C2 C 0.1426(2) 0.6354(2) 0.3664(2) 0.0345(4) Uani 1 1 d . . . . .
H2A H 0.0769 0.6029 0.3184 0.041 Uiso 1 1 calc R U . . .
H2B H 0.1555 0.5442 0.4611 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2964(2) 0.6955(3) 0.2540(3) 0.0414(5) Uani 1 1 d . . . . .
H3A H 0.3784 0.6268 0.2940 0.050 Uiso 1 1 calc R U . . .
H3B H 0.2976 0.6990 0.1522 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3144(2) 0.8612(2) 0.2425(3) 0.0401(5) Uani 1 1 d . . . . .
H4A H 0.3645 0.8582 0.3215 0.048 Uiso 1 1 calc R U . . .
H4B H 0.3737 0.9306 0.1395 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0915(2) 0.9566(2) 0.1320(2) 0.0311(4) Uani 1 1 d . . . . .
H5A H 0.0920 0.8628 0.1119 0.047 Uiso 1 1 calc R U . . .
H5B H 0.1535 1.0400 0.0425 0.047 Uiso 1 1 calc R U . . .
H5C H -0.0121 0.9930 0.1515 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1417(2) 1.0572(2) 0.3065(2) 0.0336(4) Uani 1 1 d . . . . .
H6A H 0.1967 1.1465 0.2175 0.050 Uiso 1 1 calc R U . . .
H6B H 0.1847 1.0332 0.3950 0.050 Uiso 1 1 calc R U . . .
H6C H 0.0353 1.0839 0.3310 0.050 Uiso 1 1 calc R U . . .
N1 N 0.15433(15) 0.91669(16) 0.27007(16) 0.0247(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
B1 O4 1.452(2) . ?
B1 O6 1.476(2) . ?
B1 O1 1.480(2) . ?
B1 O3 1.4889(19) . ?
B2 O7 1.359(2) . ?
B2 O1 1.361(2) . ?
B2 O2 1.388(2) . ?
B3 O3 1.362(2) . ?
B3 O8 1.3655(19) . ?
B3 O2 1.384(2) . ?
B4 O4 1.362(2) . ?
B4 O9 1.362(2) . ?
B4 O5 1.386(2) . ?
B5 O10 1.362(2) . ?
B5 O6 1.365(2) . ?
B5 O5 1.384(2) . ?
O7 H7 0.8400 . ?
O8 H8 0.8400 . ?
O9 H9 0.8400 . ?
O10 H10 0.8400 . ?
C1 N1 1.509(2) . ?
C1 C2 1.535(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.539(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.509(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.501(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N1 1.495(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
O4 B1 O6 111.94(12) . . ?
O4 B1 O1 109.18(13) . . ?
O6 B1 O1 108.14(13) . . ?
O4 B1 O3 109.29(13) . . ?
O6 B1 O3 108.59(12) . . ?
O1 B1 O3 109.68(12) . . ?
O7 B2 O1 122.66(14) . . ?
O7 B2 O2 116.50(13) . . ?
O1 B2 O2 120.83(14) . . ?
O3 B3 O8 122.11(14) . . ?
O3 B3 O2 121.53(14) . . ?
O8 B3 O2 116.34(13) . . ?
O4 B4 O9 117.83(14) . . ?
O4 B4 O5 121.63(15) . . ?
O9 B4 O5 120.54(14) . . ?
O10 B5 O6 122.13(15) . . ?
O10 B5 O5 117.00(14) . . ?
O6 B5 O5 120.86(14) . . ?
B2 O1 B1 124.40(12) . . ?
B3 O2 B2 119.14(12) . . ?
B3 O3 B1 123.44(12) . . ?
B4 O4 B1 123.03(13) . . ?
B5 O5 B4 119.09(13) . . ?
B5 O6 B1 123.19(12) . . ?
B2 O7 H7 109.5 . . ?
B3 O8 H8 109.5 . . ?
B4 O9 H9 109.5 . . ?
B5 O10 H10 109.5 . . ?
N1 C1 C2 103.90(15) . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C1 C2 C3 106.01(16) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 104.68(17) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C3 103.60(15) . . ?
N1 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
N1 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C6 N1 C5 108.81(14) . . ?
C6 N1 C4 112.50(14) . . ?
C5 N1 C4 110.51(15) . . ?
C6 N1 C1 112.22(14) . . ?
C5 N1 C1 110.19(13) . . ?
C4 N1 C1 102.51(14) . . ?

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
O7 B2 O1 B1 -177.89(14) . . . . ?
O2 B2 O1 B1 3.1(2) . . . . ?
O4 B1 O1 B2 -129.34(15) . . . . ?
O6 B1 O1 B2 108.65(15) . . . . ?
O3 B1 O1 B2 -9.6(2) . . . . ?
O3 B3 O2 B2 -1.8(2) . . . . ?
O8 B3 O2 B2 176.93(14) . . . . ?
O7 B2 O2 B3 -175.70(14) . . . . ?
O1 B2 O2 B3 3.4(2) . . . . ?
O8 B3 O3 B1 175.13(14) . . . . ?
O2 B3 O3 B1 -6.2(2) . . . . ?
O4 B1 O3 B3 130.75(14) . . . . ?
O6 B1 O3 B3 -106.88(15) . . . . ?
O1 B1 O3 B3 11.1(2) . . . . ?
O9 B4 O4 B1 173.14(12) . . . . ?
O5 B4 O4 B1 -6.1(2) . . . . ?
O6 B1 O4 B4 5.79(19) . . . . ?
O1 B1 O4 B4 -113.90(15) . . . . ?
O3 B1 O4 B4 126.14(14) . . . . ?
O10 B5 O5 B4 179.28(13) . . . . ?
O6 B5 O5 B4 0.6(2) . . . . ?
O4 B4 O5 B5 2.6(2) . . . . ?
O9 B4 O5 B5 -176.65(13) . . . . ?
O10 B5 O6 B1 -178.99(13) . . . . ?
O5 B5 O6 B1 -0.4(2) . . . . ?
O4 B1 O6 B5 -2.59(19) . . . . ?
O1 B1 O6 B5 117.72(15) . . . . ?
O3 B1 O6 B5 -123.34(14) . . . . ?
N1 C1 C2 C3 21.94(19) . . . . ?
C1 C2 C3 C4 4.6(2) . . . . ?
C2 C3 C4 N1 -29.5(2) . . . . ?
C3 C4 N1 C6 164.32(16) . . . . ?
C3 C4 N1 C5 -73.84(19) . . . . ?
C3 C4 N1 C1 43.57(19) . . . . ?
C2 C1 N1 C6 -161.33(14) . . . . ?
C2 C1 N1 C5 77.25(17) . . . . ?
C2 C1 N1 C4 -40.40(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O1 0.84 1.86 2.6933(18) 172.5 2_765
O8 H8 O3 0.84 1.87 2.702(2) 171.4 2_666
O9 H9 O8 0.84 1.94 2.746(2) 159.6 1_545
O10 H10 O6 0.84 1.93 2.763(2) 170.7 2_665
C1 H1B O4 0.99 2.60 3.495(2) 149.6 2_666

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1043677'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'B5 H4 O10, C5 H12 N O, 0.5(H2 O)'
_chemical_formula_sum            'C5 H17 B5 N O11.50'
_chemical_formula_weight         329.24

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           1
_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'

_cell_length_a                   9.1164(5)
_cell_length_b                   9.1691(5)
_cell_length_c                   9.5532(7)
_cell_angle_alpha                75.798(5)
_cell_angle_beta                 69.608(4)
_cell_angle_gamma                82.611(5)
_cell_volume                     724.81(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11300
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            11353
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.731
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             5960
_reflns_number_gt                5776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.803
_reflns_Friedel_fraction_full    0.880

_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXD-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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)+(0.0652P)²+0.1065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5960
_refine_ls_number_parameters     419
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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
B1 B 0.5962(3) 0.5672(3) 0.5448(3) 0.0160(5) Uani 1 1 d . . . . .
B2 B 0.3765(3) 0.5995(3) 0.4397(3) 0.0176(5) Uani 1 1 d . . . . .
B3 B 0.3819(3) 0.3870(3) 0.6387(3) 0.0195(5) Uani 1 1 d . . . . .
B4 B 0.8815(3) 0.6074(3) 0.4559(3) 0.0181(5) Uani 1 1 d . . . . .
B5 B 0.7097(3) 0.7413(3) 0.6387(3) 0.0198(5) Uani 1 1 d . . . . .
O1 O 0.51699(19) 0.64195(18) 0.43258(17) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.3059(2) 0.4750(2) 0.54292(19) 0.0207(3) Uani 1 1 d . . . . .
O3 O 0.52137(19) 0.42798(18) 0.63770(18) 0.0186(3) Uani 1 1 d . . . . .
O4 O 0.76008(19) 0.53248(18) 0.46011(17) 0.0177(3) Uani 1 1 d . . . . .
O5 O 0.8584(2) 0.7155(2) 0.53971(19) 0.0221(4) Uani 1 1 d . . . . .
O6 O 0.58617(19) 0.66875(18) 0.64566(17) 0.0184(3) Uani 1 1 d . . . . .
O7 O 0.2970(2) 0.68152(19) 0.34629(19) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.3498 0.7545 0.2874 0.031 Uiso 1 1 calc R U . . .
O8 O 0.3115(2) 0.2607(2) 0.7311(2) 0.0274(4) Uani 1 1 d . . . . .
H8 H 0.3694 0.2119 0.7800 0.041 Uiso 1 1 calc R U . . .
O9 O 1.0280(2) 0.5697(2) 0.3681(2) 0.0228(4) Uani 1 1 d . . . . .
H9 H 1.0939 0.6173 0.3803 0.034 Uiso 1 1 calc R U . . .
O10 O 0.6962(2) 0.8413(2) 0.7269(2) 0.0275(4) Uani 1 1 d . . . . .
H10 H 0.6043 0.8433 0.7882 0.041 Uiso 1 1 calc R U . . .
B11 B 0.3901(3) 0.9722(3) 0.0201(3) 0.0166(5) Uani 1 1 d . . . . .
B12 B 0.6041(3) 0.9480(3) 0.1332(3) 0.0186(5) Uani 1 1 d . . . . .
B13 B 0.5986(3) 1.1575(3) -0.0706(3) 0.0179(5) Uani 1 1 d . . . . .
B14 B 0.1033(3) 0.9413(3) 0.1030(3) 0.0174(5) Uani 1 1 d . . . . .
B15 B 0.2752(3) 0.7925(3) -0.0660(3) 0.0189(5) Uani 1 1 d . . . . .
O11 O 0.46919(19) 0.90079(18) 0.13313(17) 0.0181(3) Uani 1 1 d . . . . .
O12 O 0.6696(2) 1.07765(19) 0.03435(19) 0.0208(4) Uani 1 1 d . . . . .
O13 O 0.46788(19) 1.10882(17) -0.07796(18) 0.0178(3) Uani 1 1 d . . . . .
O14 O 0.22792(19) 1.00861(18) 0.10327(18) 0.0183(3) Uani 1 1 d . . . . .
O15 O 0.1257(2) 0.8288(2) 0.0227(2) 0.0210(3) Uani 1 1 d . . . . .
O16 O 0.40035(19) 0.86597(18) -0.07607(18) 0.0182(3) Uani 1 1 d . . . . .
O17 O 0.6804(2) 0.8711(2) 0.2301(2) 0.0242(4) Uani 1 1 d . . . . .
H17 H 0.6228 0.8053 0.2967 0.036 Uiso 1 1 calc R U . . .
O18 O 0.6681(2) 1.2847(2) -0.16191(19) 0.0231(4) Uani 1 1 d . . . . .
H18 H 0.6192 1.3247 -0.2228 0.035 Uiso 1 1 calc R U . . .
O19 O -0.0412(2) 0.9883(2) 0.18442(19) 0.0208(3) Uani 1 1 d . . . . .
H19 H -0.1071 0.9277 0.1931 0.031 Uiso 1 1 calc R U . . .
O20 O 0.2923(2) 0.6795(2) -0.1412(2) 0.0243(4) Uani 1 1 d . . . . .
H20 H 0.3847 0.6751 -0.2012 0.037 Uiso 1 1 calc R U . . .
C21 C 0.9671(3) 0.3238(3) -0.0412(3) 0.0260(5) Uani 1 1 d . . . . .
H21C H 0.9684 0.2461 -0.0976 0.031 Uiso 1 1 calc R U . . .
H21D H 1.0612 0.3072 -0.0091 0.031 Uiso 1 1 calc R U . . .
C22 C 0.9604(3) 0.4810(3) -0.1386(3) 0.0335(6) Uani 1 1 d . . . . .
H22A H 1.0668 0.5139 -0.2032 0.040 Uiso 1 1 calc R U . . .
H22B H 0.8969 0.4848 -0.2052 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8837(4) 0.5784(3) -0.0226(4) 0.0359(7) Uani 1 1 d . . . . .
H23A H 0.8373 0.6732 -0.0692 0.043 Uiso 1 1 calc R U . . .
H23B H 0.9607 0.6031 0.0189 0.043 Uiso 1 1 calc R U . . .
C24 C 0.7575(3) 0.4823(3) 0.1020(3) 0.0260(5) Uani 1 1 d . . . . .
H24 H 0.7452 0.5019 0.2040 0.031 Uiso 1 1 calc R U . . .
C25 C 0.6026(3) 0.5084(3) 0.0745(3) 0.0270(5) Uani 1 1 d . . . . .
H25A H 0.5566 0.6096 0.0892 0.032 Uiso 1 1 calc R U . . .
H25B H 0.6169 0.5021 -0.0315 0.032 Uiso 1 1 calc R U . . .
N21 N 0.8190(2) 0.3203(2) 0.0952(2) 0.0217(4) Uani 1 1 d . . . . .
H21A H 0.8415 0.2700 0.1903 0.026 Uiso 1 1 calc R U . . .
H21B H 0.7395 0.2633 0.0849 0.026 Uiso 1 1 calc R U . . .
O21 O 0.5026(2) 0.3963(3) 0.1799(3) 0.0451(6) Uani 1 1 d . . . . .
H21 H 0.4157 0.4076 0.1656 0.068 Uiso 1 1 calc R U . . .
C31 C 0.2739(4) 0.1418(3) 0.4291(4) 0.0369(6) Uani 1 1 d . . . . .
H31A H 0.2525 0.2286 0.4789 0.044 Uiso 1 1 calc R U . . .
H31B H 0.3804 0.1477 0.3524 0.044 Uiso 1 1 calc R U . . .
C32 C 0.2556(4) -0.0062(3) 0.5458(3) 0.0363(6) Uani 1 1 d . . . . .
H32A H 0.2982 -0.0022 0.6269 0.044 Uiso 1 1 calc R U . . .
H32B H 0.3097 -0.0906 0.4966 0.044 Uiso 1 1 calc R U . . .
C33 C 0.0768(4) -0.0239(4) 0.6116(3) 0.0362(6) Uani 1 1 d . . . . .
H33A H 0.0522 -0.1316 0.6435 0.043 Uiso 1 1 calc R U . . .
H33B H 0.0294 0.0234 0.7010 0.043 Uiso 1 1 calc R U . . .
C34 C 0.0155(3) 0.0570(3) 0.4797(3) 0.0300(5) Uani 1 1 d . . . . .
H34 H -0.0198 -0.0185 0.4398 0.036 Uiso 1 1 calc R U . . .
C35 C -0.1156(4) 0.1729(3) 0.5244(3) 0.0341(6) Uani 1 1 d . . . . .
H35A H -0.2111 0.1221 0.5969 0.041 Uiso 1 1 calc R U . . .
H35B H -0.0853 0.2402 0.5755 0.041 Uiso 1 1 calc R U . . .
N31 N 0.1531(3) 0.1359(2) 0.3582(3) 0.0285(4) Uani 1 1 d . . . . .
H31C H 0.1969 0.0806 0.2745 0.034 Uiso 1 1 calc R U . . .
H31D H 0.1201 0.2392 0.3149 0.034 Uiso 1 1 calc R U . . .
O31 O -0.1469(2) 0.2595(2) 0.3900(2) 0.0286(4) Uani 1 1 d . . . . .
H31 H -0.1779 0.3474 0.4018 0.043 Uiso 1 1 calc R U . . .
O41 O 0.2112(2) 0.4351(2) 0.1336(2) 0.0293(4) Uani 1 1 d G . . . .
H41A H 0.1384 0.4845 0.1933 0.044 Uiso 1 1 d G U . . .
H41B H 0.2376 0.4882 0.0403 0.044 Uiso 1 1 d G U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O3 1.459(3) . ?
B1 O4 1.466(3) . ?
B1 O6 1.470(3) . ?
B1 O1 1.480(3) . ?
B2 O1 1.361(3) . ?
B2 O7 1.366(3) . ?
B2 O2 1.373(3) . ?
B3 O8 1.352(3) . ?
B3 O3 1.368(3) . ?
B3 O2 1.380(3) . ?
B4 O9 1.360(3) . ?
B4 O4 1.360(3) . ?
B4 O5 1.374(3) . ?
B5 O6 1.354(3) . ?
B5 O10 1.358(3) . ?
B5 O5 1.386(3) . ?
O7 H7 0.8400 . ?
O8 H8 0.8400 . ?
O9 H9 0.8400 . ?
O10 H10 0.8400 . ?
B11 O14 1.453(3) . ?
B11 O13 1.462(3) . ?
B11 O16 1.469(3) . ?
B11 O11 1.480(3) . ?
B12 O11 1.355(3) . ?
B12 O17 1.357(3) . ?
B12 O12 1.379(3) . ?
B13 O18 1.352(3) . ?
B13 O13 1.355(3) . ?
B13 O12 1.389(3) . ?
B14 O19 1.353(3) . ?
B14 O14 1.362(3) . ?
B14 O15 1.386(3) . ?
B15 O16 1.362(3) . ?
B15 O20 1.364(3) . ?
B15 O15 1.380(3) . ?
O17 H17 0.8400 . ?
O18 H18 0.8400 . ?
O19 H19 0.8400 . ?
O20 H20 0.8400 . ?
C21 N21 1.512(3) . ?
C21 C22 1.519(4) . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C22 C23 1.516(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.519(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.504(3) . ?
C24 N21 1.527(3) . ?
C24 H24 1.0000 . ?
C25 O21 1.412(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21A 0.9900 . ?
N21 H21B 0.9900 . ?
O21 H21 0.8400 . ?
C31 N31 1.492(3) . ?
C31 C32 1.516(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.544(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.542(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N31 1.500(4) . ?
C34 C35 1.510(4) . ?
C34 H34 1.0000 . ?
C35 O31 1.434(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31C 0.9900 . ?
N31 H31D 0.9900 . ?
O31 H31 0.8400 . ?
O41 H41A 0.8703 . ?
O41 H41B 0.8700 . ?

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
O3 B1 O4 109.36(18) . . ?
O3 B1 O6 108.86(18) . . ?
O4 B1 O6 110.72(18) . . ?
O3 B1 O1 110.57(18) . . ?
O4 B1 O1 108.14(18) . . ?
O6 B1 O1 109.18(18) . . ?
O1 B2 O7 121.3(2) . . ?
O1 B2 O2 121.9(2) . . ?
O7 B2 O2 116.8(2) . . ?
O8 B3 O3 122.8(2) . . ?
O8 B3 O2 116.6(2) . . ?
O3 B3 O2 120.6(2) . . ?
O9 B4 O4 117.8(2) . . ?
O9 B4 O5 120.7(2) . . ?
O4 B4 O5 121.5(2) . . ?
O6 B5 O10 122.7(2) . . ?
O6 B5 O5 120.8(2) . . ?
O10 B5 O5 116.5(2) . . ?
B2 O1 B1 122.56(19) . . ?
B2 O2 B3 119.2(2) . . ?
B3 O3 B1 124.02(18) . . ?
B4 O4 B1 123.07(18) . . ?
B4 O5 B5 119.1(2) . . ?
B5 O6 B1 123.59(19) . . ?
B2 O7 H7 109.5 . . ?
B3 O8 H8 109.5 . . ?
B4 O9 H9 109.5 . . ?
B5 O10 H10 109.5 . . ?
O14 B11 O13 110.27(19) . . ?
O14 B11 O16 111.13(19) . . ?
O13 B11 O16 108.53(18) . . ?
O14 B11 O11 108.08(18) . . ?
O13 B11 O11 110.29(18) . . ?
O16 B11 O11 108.53(18) . . ?
O11 B12 O17 122.0(2) . . ?
O11 B12 O12 121.1(2) . . ?
O17 B12 O12 116.9(2) . . ?
O18 B13 O13 123.4(2) . . ?
O18 B13 O12 115.7(2) . . ?
O13 B13 O12 121.0(2) . . ?
O19 B14 O14 117.3(2) . . ?
O19 B14 O15 122.0(2) . . ?
O14 B14 O15 120.6(2) . . ?
O16 B15 O20 121.6(2) . . ?
O16 B15 O15 121.0(2) . . ?
O20 B15 O15 117.4(2) . . ?
B12 O11 B11 123.89(18) . . ?
B12 O12 B13 119.1(2) . . ?
B13 O13 B11 124.37(18) . . ?
B14 O14 B11 124.00(18) . . ?
B15 O15 B14 119.3(2) . . ?
B15 O16 B11 123.12(19) . . ?
B12 O17 H17 109.5 . . ?
B13 O18 H18 109.5 . . ?
B14 O19 H19 109.5 . . ?
B15 O20 H20 109.5 . . ?
N21 C21 C22 103.81(19) . . ?
N21 C21 H21C 111.0 . . ?
C22 C21 H21C 111.0 . . ?
N21 C21 H21D 111.0 . . ?
C22 C21 H21D 111.0 . . ?
H21C C21 H21D 109.0 . . ?
C23 C22 C21 103.9(2) . . ?
C23 C22 H22A 111.0 . . ?
C21 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C22 C23 C24 104.3(2) . . ?
C22 C23 H23A 110.9 . . ?
C24 C23 H23A 110.9 . . ?
C22 C23 H23B 110.9 . . ?
C24 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
C25 C24 C23 112.5(2) . . ?
C25 C24 N21 109.6(2) . . ?
C23 C24 N21 104.5(2) . . ?
C25 C24 H24 110.0 . . ?
C23 C24 H24 110.0 . . ?
N21 C24 H24 110.0 . . ?
O21 C25 C24 107.8(2) . . ?
O21 C25 H25A 110.2 . . ?
C24 C25 H25A 110.2 . . ?
O21 C25 H25B 110.2 . . ?
C24 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C21 N21 C24 108.37(19) . . ?
C21 N21 H21A 110.0 . . ?
C24 N21 H21A 110.0 . . ?
C21 N21 H21B 110.0 . . ?
C24 N21 H21B 110.0 . . ?
H21A N21 H21B 108.4 . . ?
C25 O21 H21 109.5 . . ?
N31 C31 C32 102.3(2) . . ?
N31 C31 H31A 111.3 . . ?
C32 C31 H31A 111.3 . . ?
N31 C31 H31B 111.3 . . ?
C32 C31 H31B 111.3 . . ?
H31A C31 H31B 109.2 . . ?
C31 C32 C33 103.8(2) . . ?
C31 C32 H32A 111.0 . . ?
C33 C32 H32A 111.0 . . ?
C31 C32 H32B 111.0 . . ?
C33 C32 H32B 111.0 . . ?
H32A C32 H32B 109.0 . . ?
C34 C33 C32 104.9(2) . . ?
C34 C33 H33A 110.8 . . ?
C32 C33 H33A 110.8 . . ?
C34 C33 H33B 110.8 . . ?
C32 C33 H33B 110.8 . . ?
H33A C33 H33B 108.8 . . ?
N31 C34 C35 108.6(2) . . ?
N31 C34 C33 105.2(2) . . ?
C35 C34 C33 113.2(2) . . ?
N31 C34 H34 109.9 . . ?
C35 C34 H34 109.9 . . ?
C33 C34 H34 109.9 . . ?
O31 C35 C34 109.3(2) . . ?
O31 C35 H35A 109.8 . . ?
C34 C35 H35A 109.8 . . ?
O31 C35 H35B 109.8 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.3 . . ?
C31 N31 C34 108.3(2) . . ?
C31 N31 H31C 110.0 . . ?
C34 N31 H31C 110.0 . . ?
C31 N31 H31D 110.0 . . ?
C34 N31 H31D 110.0 . . ?
H31C N31 H31D 108.4 . . ?
C35 O31 H31 109.5 . . ?
H41A O41 H41B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 B2 O1 B1 172.0(2) . . . . ?
O2 B2 O1 B1 -6.4(3) . . . . ?
O3 B1 O1 B2 12.1(3) . . . . ?
O4 B1 O1 B2 131.8(2) . . . . ?
O6 B1 O1 B2 -107.7(2) . . . . ?
O1 B2 O2 B3 -2.4(3) . . . . ?
O7 B2 O2 B3 179.1(2) . . . . ?
O8 B3 O2 B2 -176.0(2) . . . . ?
O3 B3 O2 B2 4.0(3) . . . . ?
O8 B3 O3 B1 -176.8(2) . . . . ?
O2 B3 O3 B1 3.2(3) . . . . ?
O4 B1 O3 B3 -129.5(2) . . . . ?
O6 B1 O3 B3 109.4(2) . . . . ?
O1 B1 O3 B3 -10.6(3) . . . . ?
O9 B4 O4 B1 -177.1(2) . . . . ?
O5 B4 O4 B1 4.1(3) . . . . ?
O3 B1 O4 B4 -131.3(2) . . . . ?
O6 B1 O4 B4 -11.4(3) . . . . ?
O1 B1 O4 B4 108.2(2) . . . . ?
O9 B4 O5 B5 -174.2(2) . . . . ?
O4 B4 O5 B5 4.6(3) . . . . ?
O6 B5 O5 B4 -4.5(3) . . . . ?
O10 B5 O5 B4 175.2(2) . . . . ?
O10 B5 O6 B1 176.1(2) . . . . ?
O5 B5 O6 B1 -4.2(3) . . . . ?
O3 B1 O6 B5 131.7(2) . . . . ?
O4 B1 O6 B5 11.5(3) . . . . ?
O1 B1 O6 B5 -107.5(2) . . . . ?
O17 B12 O11 B11 -173.8(2) . . . . ?
O12 B12 O11 B11 6.4(3) . . . . ?
O14 B11 O11 B12 -127.1(2) . . . . ?
O13 B11 O11 B12 -6.5(3) . . . . ?
O16 B11 O11 B12 112.3(2) . . . . ?
O11 B12 O12 B13 -2.4(3) . . . . ?
O17 B12 O12 B13 177.8(2) . . . . ?
O18 B13 O12 B12 178.9(2) . . . . ?
O13 B13 O12 B12 -0.8(3) . . . . ?
O18 B13 O13 B11 -179.6(2) . . . . ?
O12 B13 O13 B11 0.1(3) . . . . ?
O14 B11 O13 B13 122.5(2) . . . . ?
O16 B11 O13 B13 -115.6(2) . . . . ?
O11 B11 O13 B13 3.2(3) . . . . ?
O19 B14 O14 B11 -179.2(2) . . . . ?
O15 B14 O14 B11 1.2(3) . . . . ?
O13 B11 O14 B14 126.4(2) . . . . ?
O16 B11 O14 B14 6.0(3) . . . . ?
O11 B11 O14 B14 -113.0(2) . . . . ?
O16 B15 O15 B14 -0.3(3) . . . . ?
O20 B15 O15 B14 179.0(2) . . . . ?
O19 B14 O15 B15 175.9(2) . . . . ?
O14 B14 O15 B15 -4.5(3) . . . . ?
O20 B15 O16 B11 -170.8(2) . . . . ?
O15 B15 O16 B11 8.5(3) . . . . ?
O14 B11 O16 B15 -10.8(3) . . . . ?
O13 B11 O16 B15 -132.2(2) . . . . ?
O11 B11 O16 B15 107.9(2) . . . . ?
N21 C21 C22 C23 34.7(3) . . . . ?
C21 C22 C23 C24 -39.3(3) . . . . ?
C22 C23 C24 C25 -91.0(3) . . . . ?
C22 C23 C24 N21 27.8(3) . . . . ?
C23 C24 C25 O21 169.8(2) . . . . ?
N21 C24 C25 O21 54.0(3) . . . . ?
C22 C21 N21 C24 -17.5(2) . . . . ?
C25 C24 N21 C21 114.4(2) . . . . ?
C23 C24 N21 C21 -6.3(2) . . . . ?
N31 C31 C32 C33 -39.3(3) . . . . ?
C31 C32 C33 C34 29.9(3) . . . . ?
C32 C33 C34 N31 -8.8(3) . . . . ?
C32 C33 C34 C35 -127.2(3) . . . . ?
N31 C34 C35 O31 53.9(3) . . . . ?
C33 C34 C35 O31 170.3(2) . . . . ?
C32 C31 N31 C34 34.9(3) . . . . ?
C35 C34 N31 C31 105.4(2) . . . . ?
C33 C34 N31 C31 -16.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O11 0.84 1.86 2.688(2) 171.1 .
O8 H8 O13 0.84 1.88 2.712(2) 169.2 1_546
O9 H9 O7 0.84 1.91 2.701(2) 156.4 1_655
O10 H10 O16 0.84 1.88 2.717(2) 175.0 1_556
O17 H17 O1 0.84 1.84 2.680(2) 172.2 .
O18 H18 O3 0.84 1.86 2.698(2) 175.0 1_564
O19 H19 O17 0.84 1.96 2.736(2) 153.4 1_455
O20 H20 O6 0.84 1.91 2.750(2) 174.1 1_554
N21 H21A O31 0.99 1.93 2.853(3) 154.7 1_655
N21 H21B O12 0.99 2.11 3.018(3) 152.3 1_545
O21 H21 O41 0.84 1.97 2.807(3) 179.5 .
N31 H31C O14 0.99 1.83 2.791(3) 162.7 1_545
N31 H31D O41 0.99 2.18 3.018(3) 140.8 .
O31 H31 O4 0.84 1.87 2.704(2) 170.0 1_455
O41 H41A O9 0.87 1.92 2.748(2) 159.0 1_455
O41 H41B O20 0.87 2.11 2.940(3) 158.8 .

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

