# Electronic Supplementary Material (ESI) for ChemComm.
# 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_d13232twin
_database_code_depnum_ccdc_archive 'CCDC 1021097'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

# start Validation Reply Form
_vrf_PLAT019_d13232twin          
;
PROBLEM: Check _diffrn_measured_fraction_theta_full/_max       0.975       
RESPONSE: 97.9% of the data were measured to the required thata max. 
For CuKalpha radiation and the geometry of this type of diffractomer 
we feel this is acceptable. The good precision of the structure is 
reflected in the R-factors and the standard unceratinties of the 
geometric parameters, especially in a structure with slight
twinning.
;
# end Validation Reply Form

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 B N2 O9'
_chemical_formula_sum            'C20 H19 B N2 O9'
_chemical_formula_weight         442.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   16.8086(4)
_cell_length_b                   10.0372(2)
_cell_length_c                   24.1763(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.321(2)
_cell_angle_gamma                90
_cell_volume                     4078.75(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    5316
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      66.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.968
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13647
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.656
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             3520
_reflns_number_gt                3213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+12.2499P] 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         3520
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66947(12) 0.97663(18) 0.32619(8) 0.0338(4) Uani 1 1 d . . . . .
O2 O 0.74300(13) 0.9873(2) 0.24963(8) 0.0416(5) Uani 1 1 d . . . . .
O3 O 0.54038(11) 0.87250(19) 0.33722(7) 0.0317(4) Uani 1 1 d . . . . .
O4 O 0.45276(11) 0.7263(2) 0.30328(7) 0.0373(5) Uani 1 1 d . . . . .
O5 O 0.66965(12) 0.7682(3) 0.51992(9) 0.0517(6) Uani 1 1 d . . . . .
O6 O 0.53993(10) 0.7793(2) 0.54435(7) 0.0339(5) Uani 1 1 d . . . . .
O7 O 0.50244(10) 0.90094(19) 0.45778(7) 0.0302(4) Uani 1 1 d . . . . .
O8 O 0.43973(11) 0.70695(19) 0.43402(7) 0.0312(4) Uani 1 1 d . . . . .
O9 O 0.37733(10) 0.90495(19) 0.45113(7) 0.0306(4) Uani 1 1 d . . . . .
N1 N 0.65759(12) 0.7370(2) 0.33535(8) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.57617(12) 0.8304(2) 0.45680(9) 0.0310(5) Uani 1 1 d . . . . .
C1 C 0.69280(15) 0.7756(2) 0.28053(10) 0.0245(5) Uani 1 1 d . . . . .
H1A H 0.6559 0.7526 0.2499 0.029 Uiso 1 1 calc R U . . .
H1B H 0.7438 0.7286 0.2746 0.029 Uiso 1 1 calc R U . . .
C2 C 0.70595(16) 0.9245(3) 0.28282(10) 0.0284(6) Uani 1 1 d . . . . .
C3 C 0.58514(15) 0.6538(3) 0.32848(11) 0.0273(6) Uani 1 1 d . . . . .
H3A H 0.5764 0.5978 0.3616 0.033 Uiso 1 1 calc R U . . .
H3B H 0.5898 0.5953 0.2957 0.033 Uiso 1 1 calc R U . . .
C4 C 0.51793(15) 0.7525(3) 0.32097(10) 0.0279(6) Uani 1 1 d . . . . .
C5 C 0.71963(16) 0.6719(3) 0.37112(11) 0.0299(6) Uani 1 1 d . . . . .
H5A H 0.7362 0.5877 0.3542 0.045 Uiso 1 1 calc R U . . .
H5B H 0.6975 0.6544 0.4078 0.045 Uiso 1 1 calc R U . . .
H5C H 0.7657 0.7311 0.3747 0.045 Uiso 1 1 calc R U . . .
C6 C 0.63227(16) 0.9079(3) 0.42227(11) 0.0332(6) Uani 1 1 d . . . . .
H6A H 0.6873 0.8865 0.4340 0.040 Uiso 1 1 calc R U . . .
H6B H 0.6235 1.0041 0.4291 0.040 Uiso 1 1 calc R U . . .
C7 C 0.60214(15) 0.7935(3) 0.50929(11) 0.0337(6) Uani 1 1 d . . . . .
C8 C 0.56138(15) 0.7437(3) 0.59913(11) 0.0291(6) Uani 1 1 d . . . . .
C9 C 0.58058(17) 0.6143(3) 0.61159(13) 0.0406(7) Uani 1 1 d . . . . .
H9A H 0.5827 0.5480 0.5836 0.049 Uiso 1 1 calc R U . . .
C10 C 0.5968(2) 0.5833(4) 0.66644(16) 0.0516(9) Uani 1 1 d . . . . .
H10A H 0.6111 0.4947 0.6762 0.062 Uiso 1 1 calc R U . . .
C11 C 0.59253(18) 0.6793(4) 0.70690(13) 0.0473(8) Uani 1 1 d . . . . .
H11A H 0.6037 0.6568 0.7443 0.057 Uiso 1 1 calc R U . . .
C12 C 0.57207(17) 0.8080(3) 0.69325(12) 0.0403(7) Uani 1 1 d . . . . .
H12A H 0.5683 0.8738 0.7213 0.048 Uiso 1 1 calc R U . . .
C13 C 0.55697(15) 0.8417(3) 0.63851(11) 0.0317(6) Uani 1 1 d . . . . .
H13A H 0.5439 0.9306 0.6285 0.038 Uiso 1 1 calc R U . . .
C14 C 0.43926(15) 0.8219(3) 0.44590(10) 0.0258(5) Uani 1 1 d . . . . .
C15 C 0.30151(15) 0.8640(3) 0.43236(10) 0.0267(5) Uani 1 1 d . . . . .
C16 C 0.23834(16) 0.8969(3) 0.46533(11) 0.0329(6) Uani 1 1 d . . . . .
H16A H 0.2467 0.9385 0.5002 0.040 Uiso 1 1 calc R U . . .
C17 C 0.16211(17) 0.8684(3) 0.44689(13) 0.0411(7) Uani 1 1 d . . . . .
H17A H 0.1177 0.8898 0.4693 0.049 Uiso 1 1 calc R U . . .
C18 C 0.15046(17) 0.8087(3) 0.39589(13) 0.0412(7) Uani 1 1 d . . . . .
H18A H 0.0981 0.7894 0.3833 0.049 Uiso 1 1 calc R U . . .
C19 C 0.21477(18) 0.7776(3) 0.36361(13) 0.0391(7) Uani 1 1 d . . . . .
H19A H 0.2063 0.7364 0.3287 0.047 Uiso 1 1 calc R U . . .
C20 C 0.29156(16) 0.8052(3) 0.38093(11) 0.0317(6) Uani 1 1 d . . . . .
H20A H 0.3360 0.7844 0.3584 0.038 Uiso 1 1 calc R U . . .
B1 B 0.62373(18) 0.8803(3) 0.35786(12) 0.0282(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.325(3) . ?
O1 B1 1.455(4) . ?
O2 C2 1.198(3) . ?
O3 C4 1.321(3) . ?
O3 B1 1.487(3) . ?
O4 C4 1.203(3) . ?
O5 C7 1.190(3) . ?
O6 C7 1.357(3) . ?
O6 C8 1.416(3) . ?
O7 C14 1.355(3) . ?
O7 N2 1.428(3) . ?
O8 C14 1.189(3) . ?
O9 C14 1.340(3) . ?
O9 C15 1.411(3) . ?
N1 C3 1.485(3) . ?
N1 C5 1.501(3) . ?
N1 C1 1.505(3) . ?
N1 B1 1.641(3) . ?
N2 C7 1.390(4) . ?
N2 C6 1.483(4) . ?
C1 C2 1.511(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 B1 1.587(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.371(4) . ?
C8 C13 1.371(4) . ?
C9 C10 1.388(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.376(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C16 1.372(4) . ?
C15 C20 1.386(4) . ?
C16 C17 1.384(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.383(5) . ?
C17 H17A 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.383(4) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 B1 113.7(2) . . ?
C4 O3 B1 114.5(2) . . ?
C7 O6 C8 114.7(2) . . ?
C14 O7 N2 112.69(19) . . ?
C14 O9 C15 119.3(2) . . ?
C3 N1 C5 112.7(2) . . ?
C3 N1 C1 111.86(19) . . ?
C5 N1 C1 110.13(19) . . ?
C3 N1 B1 104.13(19) . . ?
C5 N1 B1 115.59(19) . . ?
C1 N1 B1 101.83(18) . . ?
C7 N2 O7 112.67(19) . . ?
C7 N2 C6 117.2(2) . . ?
O7 N2 C6 107.7(2) . . ?
N1 C1 C2 106.3(2) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O2 C2 O1 124.5(3) . . ?
O2 C2 C1 124.9(2) . . ?
O1 C2 C1 110.6(2) . . ?
N1 C3 C4 104.9(2) . . ?
N1 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
N1 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
O4 C4 O3 124.3(3) . . ?
O4 C4 C3 125.3(3) . . ?
O3 C4 C3 110.4(2) . . ?
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 . . ?
N2 C6 B1 114.0(2) . . ?
N2 C6 H6A 108.8 . . ?
B1 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
B1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O5 C7 O6 125.4(3) . . ?
O5 C7 N2 123.3(2) . . ?
O6 C7 N2 111.0(2) . . ?
C9 C8 C13 122.7(3) . . ?
C9 C8 O6 120.2(3) . . ?
C13 C8 O6 117.0(2) . . ?
C8 C9 C10 117.8(3) . . ?
C8 C9 H9A 121.1 . . ?
C10 C9 H9A 121.1 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C8 C13 C12 118.5(3) . . ?
C8 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
O8 C14 O9 129.2(2) . . ?
O8 C14 O7 127.8(2) . . ?
O9 C14 O7 103.0(2) . . ?
C16 C15 C20 122.3(2) . . ?
C16 C15 O9 116.3(2) . . ?
C20 C15 O9 121.1(2) . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16A 120.6 . . ?
C17 C16 H16A 120.6 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19A 119.4 . . ?
C20 C19 H19A 119.4 . . ?
C19 C20 C15 117.7(3) . . ?
C19 C20 H20A 121.2 . . ?
C15 C20 H20A 121.2 . . ?
O1 B1 O3 111.0(2) . . ?
O1 B1 C6 110.8(2) . . ?
O3 B1 C6 114.7(2) . . ?
O1 B1 N1 102.8(2) . . ?
O3 B1 N1 99.8(2) . . ?
C6 B1 N1 116.7(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
C14 O7 N2 C7 -98.8(3) . . . . ?
C14 O7 N2 C6 130.5(2) . . . . ?
C3 N1 C1 C2 130.2(2) . . . . ?
C5 N1 C1 C2 -103.6(2) . . . . ?
B1 N1 C1 C2 19.6(2) . . . . ?
B1 O1 C2 O2 175.7(3) . . . . ?
B1 O1 C2 C1 -3.1(3) . . . . ?
N1 C1 C2 O2 169.2(2) . . . . ?
N1 C1 C2 O1 -11.9(3) . . . . ?
C5 N1 C3 C4 149.9(2) . . . . ?
C1 N1 C3 C4 -85.3(2) . . . . ?
B1 N1 C3 C4 23.9(2) . . . . ?
B1 O3 C4 O4 179.7(2) . . . . ?
B1 O3 C4 C3 0.3(3) . . . . ?
N1 C3 C4 O4 164.2(2) . . . . ?
N1 C3 C4 O3 -16.5(3) . . . . ?
C7 N2 C6 B1 148.0(2) . . . . ?
O7 N2 C6 B1 -83.8(3) . . . . ?
C8 O6 C7 O5 6.5(4) . . . . ?
C8 O6 C7 N2 -179.1(2) . . . . ?
O7 N2 C7 O5 -158.6(3) . . . . ?
C6 N2 C7 O5 -32.8(4) . . . . ?
O7 N2 C7 O6 26.8(3) . . . . ?
C6 N2 C7 O6 152.6(2) . . . . ?
C7 O6 C8 C9 -78.7(3) . . . . ?
C7 O6 C8 C13 105.3(3) . . . . ?
C13 C8 C9 C10 -0.7(4) . . . . ?
O6 C8 C9 C10 -176.5(3) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
O6 C8 C13 C12 175.5(2) . . . . ?
C11 C12 C13 C8 1.3(4) . . . . ?
C15 O9 C14 O8 -11.4(4) . . . . ?
C15 O9 C14 O7 168.8(2) . . . . ?
N2 O7 C14 O8 -2.1(4) . . . . ?
N2 O7 C14 O9 177.69(18) . . . . ?
C14 O9 C15 C16 139.2(2) . . . . ?
C14 O9 C15 C20 -46.6(3) . . . . ?
C20 C15 C16 C17 1.0(4) . . . . ?
O9 C15 C16 C17 175.1(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 C15 0.7(4) . . . . ?
C16 C15 C20 C19 -1.1(4) . . . . ?
O9 C15 C20 C19 -174.9(3) . . . . ?
C2 O1 B1 O3 -90.6(3) . . . . ?
C2 O1 B1 C6 140.7(2) . . . . ?
C2 O1 B1 N1 15.4(3) . . . . ?
C4 O3 B1 O1 122.1(2) . . . . ?
C4 O3 B1 C6 -111.4(3) . . . . ?
C4 O3 B1 N1 14.1(3) . . . . ?
N2 C6 B1 O1 169.4(2) . . . . ?
N2 C6 B1 O3 42.7(3) . . . . ?
N2 C6 B1 N1 -73.5(3) . . . . ?
C3 N1 B1 O1 -137.4(2) . . . . ?
C5 N1 B1 O1 98.4(2) . . . . ?
C1 N1 B1 O1 -20.9(2) . . . . ?
C3 N1 B1 O3 -23.0(2) . . . . ?
C5 N1 B1 O3 -147.2(2) . . . . ?
C1 N1 B1 O3 93.4(2) . . . . ?
C3 N1 B1 C6 101.2(3) . . . . ?
C5 N1 B1 C6 -23.0(3) . . . . ?
C1 N1 B1 C6 -142.4(2) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_d1360
_database_code_depnum_ccdc_archive 'CCDC 1021098'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 B Cl N5 O4, 4(H2 O)'
_chemical_formula_sum            'C11 H19 B Cl N5 O8'
_chemical_formula_weight         395.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   14.3477(18)
_cell_length_b                   6.9395(7)
_cell_length_c                   17.098(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.140(3)
_cell_angle_gamma                90.00
_cell_volume                     1698.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    4463
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.45

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Bruker Triumph'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15259
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.51
_reflns_number_total             3886
_reflns_number_gt                3234
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0379P)²+0.7025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3886
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.40436(2) 0.32818(5) 0.58131(2) 0.01948(10) Uani 1 1 d . . .
O1 O 0.79896(7) 0.41950(15) 0.40250(6) 0.0172(2) Uani 1 1 d . . .
O2 O 0.78318(8) 0.64292(16) 0.30808(6) 0.0235(2) Uani 1 1 d . . .
O3 O 0.89656(7) 0.21776(15) 0.49025(6) 0.0185(2) Uani 1 1 d . . .
O4 O 1.04339(8) 0.28148(17) 0.53609(6) 0.0253(3) Uani 1 1 d . . .
N1 N 0.91657(8) 0.21893(17) 0.35007(6) 0.0123(2) Uani 1 1 d . . .
N2 N 0.68667(8) 0.11035(18) 0.46073(7) 0.0151(2) Uani 1 1 d . . .
N3 N 0.61861(8) 0.17289(18) 0.57294(7) 0.0173(3) Uani 1 1 d . . .
N4 N 0.42178(8) 0.29886(18) 0.43039(7) 0.0186(3) Uani 1 1 d . . .
N5 N 0.55738(9) 0.19174(18) 0.36666(7) 0.0183(3) Uani 1 1 d . . .
C1 C 0.88181(10) 0.3669(2) 0.29126(8) 0.0168(3) Uani 1 1 d . . .
H1A H 0.8479 0.3047 0.2455 0.020 Uiso 1 1 calc R . .
H1B H 0.9345 0.4425 0.2728 0.020 Uiso 1 1 calc R . .
C2 C 0.81679(9) 0.4953(2) 0.33395(8) 0.0159(3) Uani 1 1 d . . .
C3 C 1.00437(9) 0.2817(2) 0.39640(8) 0.0175(3) Uani 1 1 d . . .
H3A H 1.0192 0.4173 0.3843 0.021 Uiso 1 1 calc R . .
H3B H 1.0577 0.1996 0.3837 0.021 Uiso 1 1 calc R . .
C4 C 0.98571(10) 0.2607(2) 0.48212(8) 0.0167(3) Uani 1 1 d . . .
C5 C 0.92922(10) 0.0267(2) 0.31266(8) 0.0187(3) Uani 1 1 d . . .
H5A H 0.9763 0.0370 0.2741 0.028 Uiso 1 1 calc R . .
H5B H 0.8697 -0.0154 0.2864 0.028 Uiso 1 1 calc R . .
H5C H 0.9499 -0.0674 0.3530 0.028 Uiso 1 1 calc R . .
C6 C 0.76069(10) 0.0614(2) 0.40840(8) 0.0174(3) Uani 1 1 d . . .
H6A H 0.7338 0.0532 0.3535 0.021 Uiso 1 1 calc R . .
H6B H 0.7882 -0.0653 0.4233 0.021 Uiso 1 1 calc R . .
C7 C 0.69444(10) 0.1133(2) 0.54109(8) 0.0169(3) Uani 1 1 d . . .
H7A H 0.7497 0.0757 0.5712 0.020 Uiso 1 1 calc R . .
C8 C 0.55698(10) 0.2119(2) 0.50924(8) 0.0146(3) Uani 1 1 d . . .
C9 C 0.46567(10) 0.2758(2) 0.50047(8) 0.0161(3) Uani 1 1 d . . .
C10 C 0.46979(10) 0.2552(2) 0.36736(9) 0.0206(3) Uani 1 1 d . . .
H10A H 0.4370 0.2718 0.3175 0.025 Uiso 1 1 calc R . .
C11 C 0.59841(10) 0.1734(2) 0.43871(8) 0.0148(3) Uani 1 1 d . . .
B1 B 0.83968(10) 0.2240(2) 0.41561(9) 0.0140(3) Uani 1 1 d . . .
O2W O 0.22264(9) 0.3934(2) 0.43647(7) 0.0301(3) Uani 1 1 d . . .
O4W O 0.80805(10) 0.0166(2) 0.71184(8) 0.0337(3) Uani 1 1 d . . .
O1W O 0.58489(8) 0.21362(18) 0.73222(7) 0.0244(3) Uani 1 1 d . . .
O3W O 0.65650(10) -0.1015(2) 0.80977(8) 0.0362(3) Uani 1 1 d . . .
H1WA H 0.5910(16) 0.203(3) 0.6844(14) 0.046(6) Uiso 1 1 d . . .
H1WB H 0.6087(15) 0.112(3) 0.7546(12) 0.037(6) Uiso 1 1 d . . .
H2WA H 0.2792(18) 0.369(3) 0.4334(13) 0.051(7) Uiso 1 1 d . . .
H2WB H 0.2146(18) 0.416(4) 0.4839(16) 0.066(8) Uiso 1 1 d . . .
H3WA H 0.6644(18) -0.217(4) 0.8063(15) 0.056(8) Uiso 1 1 d . . .
H3WB H 0.6791(16) -0.060(3) 0.8540(14) 0.049(7) Uiso 1 1 d . . .
H4WA H 0.8440(18) -0.071(4) 0.7277(14) 0.053(7) Uiso 1 1 d . . .
H4WB H 0.761(2) 0.000(4) 0.7376(16) 0.069(9) 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
Cl1 C9 1.7297(14) . ?
O1 C2 1.3261(17) . ?
O1 B1 1.4879(19) . ?
O2 C2 1.2031(18) . ?
O3 C4 1.3304(17) . ?
O3 B1 1.4650(18) . ?
O4 C4 1.2030(17) . ?
N1 C5 1.4960(18) . ?
N1 C1 1.4974(18) . ?
N1 C3 1.5032(17) . ?
N1 B1 1.6286(18) . ?
N2 C11 1.3668(18) . ?
N2 C7 1.3706(18) . ?
N2 C6 1.4768(17) . ?
N3 C7 1.3180(18) . ?
N3 C8 1.3792(18) . ?
N4 C9 1.3226(19) . ?
N4 C10 1.3547(19) . ?
N5 C10 1.3325(19) . ?
N5 C11 1.3326(18) . ?
C1 C2 1.5148(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.5158(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 B1 1.597(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(2) . ?
C8 C11 1.4081(18) . ?
C10 H10A 0.9500 . ?
O2W H2WA 0.83(3) . ?
O2W H2WB 0.84(3) . ?
O4W H4WA 0.83(3) . ?
O4W H4WB 0.84(3) . ?
O1W H1WA 0.83(2) . ?
O1W H1WB 0.86(2) . ?
O3W H3WA 0.81(3) . ?
O3W H3WB 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 B1 113.32(11) . . ?
C4 O3 B1 112.43(11) . . ?
C5 N1 C1 111.67(11) . . ?
C5 N1 C3 111.14(11) . . ?
C1 N1 C3 112.40(11) . . ?
C5 N1 B1 114.99(11) . . ?
C1 N1 B1 103.77(10) . . ?
C3 N1 B1 102.40(10) . . ?
C11 N2 C7 106.14(11) . . ?
C11 N2 C6 126.81(12) . . ?
C7 N2 C6 126.93(12) . . ?
C7 N3 C8 103.69(12) . . ?
C9 N4 C10 117.22(13) . . ?
C10 N5 C11 112.16(12) . . ?
N1 C1 C2 105.46(11) . . ?
N1 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
N1 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
O2 C2 O1 124.39(13) . . ?
O2 C2 C1 124.61(13) . . ?
O1 C2 C1 110.95(12) . . ?
N1 C3 C4 106.37(11) . . ?
N1 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
N1 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.6 . . ?
O4 C4 O3 124.05(13) . . ?
O4 C4 C3 124.79(13) . . ?
O3 C4 C3 111.15(11) . . ?
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 . . ?
N2 C6 B1 109.16(11) . . ?
N2 C6 H6A 109.8 . . ?
B1 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
B1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N3 C7 N2 114.15(13) . . ?
N3 C7 H7A 122.9 . . ?
N2 C7 H7A 122.9 . . ?
N3 C8 C9 134.26(13) . . ?
N3 C8 C11 110.66(12) . . ?
C9 C8 C11 115.07(13) . . ?
N4 C9 C8 121.55(13) . . ?
N4 C9 Cl1 117.53(11) . . ?
C8 C9 Cl1 120.93(11) . . ?
N5 C10 N4 127.97(14) . . ?
N5 C10 H10A 116.0 . . ?
N4 C10 H10A 116.0 . . ?
N5 C11 N2 128.60(13) . . ?
N5 C11 C8 126.02(13) . . ?
N2 C11 C8 105.36(12) . . ?
O3 B1 O1 110.25(12) . . ?
O3 B1 C6 113.20(12) . . ?
O1 B1 C6 111.32(11) . . ?
O3 B1 N1 103.67(10) . . ?
O1 B1 N1 101.19(11) . . ?
C6 B1 N1 116.35(11) . . ?
H2WA O2W H2WB 107(2) . . ?
H4WA O4W H4WB 103(2) . . ?
H1WA O1W H1WB 107(2) . . ?
H3WA O3W H3WB 111(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
C5 N1 C1 C2 144.56(11) . . . . ?
C3 N1 C1 C2 -89.75(13) . . . . ?
B1 N1 C1 C2 20.13(13) . . . . ?
B1 O1 C2 O2 172.39(14) . . . . ?
B1 O1 C2 C1 -5.25(16) . . . . ?
N1 C1 C2 O2 171.69(13) . . . . ?
N1 C1 C2 O1 -10.68(15) . . . . ?
C5 N1 C3 C4 -107.00(13) . . . . ?
C1 N1 C3 C4 127.02(12) . . . . ?
B1 N1 C3 C4 16.28(14) . . . . ?
B1 O3 C4 O4 173.08(14) . . . . ?
B1 O3 C4 C3 -6.39(17) . . . . ?
N1 C3 C4 O4 172.96(14) . . . . ?
N1 C3 C4 O3 -7.58(16) . . . . ?
C11 N2 C6 B1 108.22(15) . . . . ?
C7 N2 C6 B1 -67.33(18) . . . . ?
C8 N3 C7 N2 -0.07(17) . . . . ?
C11 N2 C7 N3 0.04(17) . . . . ?
C6 N2 C7 N3 176.34(13) . . . . ?
C7 N3 C8 C9 178.92(16) . . . . ?
C7 N3 C8 C11 0.08(16) . . . . ?
C10 N4 C9 C8 0.7(2) . . . . ?
C10 N4 C9 Cl1 -179.16(11) . . . . ?
N3 C8 C9 N4 -179.02(15) . . . . ?
C11 C8 C9 N4 -0.2(2) . . . . ?
N3 C8 C9 Cl1 0.8(2) . . . . ?
C11 C8 C9 Cl1 179.62(10) . . . . ?
C11 N5 C10 N4 -0.3(2) . . . . ?
C9 N4 C10 N5 -0.4(2) . . . . ?
C10 N5 C11 N2 179.03(14) . . . . ?
C10 N5 C11 C8 0.9(2) . . . . ?
C7 N2 C11 N5 -178.45(14) . . . . ?
C6 N2 C11 N5 5.2(2) . . . . ?
C7 N2 C11 C8 0.01(15) . . . . ?
C6 N2 C11 C8 -176.29(13) . . . . ?
N3 C8 C11 N5 178.46(13) . . . . ?
C9 C8 C11 N5 -0.6(2) . . . . ?
N3 C8 C11 N2 -0.06(16) . . . . ?
C9 C8 C11 N2 -179.14(12) . . . . ?
C4 O3 B1 O1 -91.18(13) . . . . ?
C4 O3 B1 C6 143.39(12) . . . . ?
C4 O3 B1 N1 16.44(15) . . . . ?
C2 O1 B1 O3 126.61(12) . . . . ?
C2 O1 B1 C6 -106.90(13) . . . . ?
C2 O1 B1 N1 17.35(14) . . . . ?
N2 C6 B1 O3 71.84(15) . . . . ?
N2 C6 B1 O1 -53.01(15) . . . . ?
N2 C6 B1 N1 -168.21(11) . . . . ?
C5 N1 B1 O3 101.08(13) . . . . ?
C1 N1 B1 O3 -136.67(11) . . . . ?
C3 N1 B1 O3 -19.57(14) . . . . ?
C5 N1 B1 O1 -144.64(11) . . . . ?
C1 N1 B1 O1 -22.40(13) . . . . ?
C3 N1 B1 O1 94.70(12) . . . . ?
C5 N1 B1 C6 -23.87(17) . . . . ?
C1 N1 B1 C6 98.37(14) . . . . ?
C3 N1 B1 C6 -144.53(13) . . . . ?

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
O1W H1WA N3 0.83(2) 1.98(2) 2.8144(17) 174(2) .
O1W H1WB O3W 0.86(2) 1.86(2) 2.7201(19) 176(2) .
O2W H2WA N4 0.83(3) 2.11(3) 2.9406(18) 177(2) .
O2W H2WB O1 0.84(3) 2.27(3) 3.0800(16) 161(3) 3_666
O3W H3WA O4W 0.81(3) 1.92(3) 2.729(2) 173(3) 2_646
O3W H3WB O2W 0.85(3) 1.89(3) 2.717(2) 162(2) 4_666
O4W H4WA O1W 0.83(3) 1.91(3) 2.7357(19) 174(2) 2_646
O4W H4WB O3W 0.84(3) 2.13(3) 2.955(2) 167(3) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051


####################################################################### 
# 
# 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_d1357
_database_code_depnum_ccdc_archive 'CCDC 1021099'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 B N6 O8, H2 O'
_chemical_formula_sum            'C21 H31 B N6 O9'
_chemical_formula_weight         522.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   19.2489(7)
_cell_length_b                   7.1031(2)
_cell_length_c                   20.6727(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.222(0)
_cell_angle_gamma                90.00
_cell_volume                     2557.04(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    7414
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      66.13

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Bruker ImuS'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17278
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         66.47
_reflns_number_total             4414
_reflns_number_gt                3934
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.6719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4414
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49123(5) 0.53988(12) 1.10850(5) 0.0199(2) Uani 1 1 d . . .
O2 O 0.56402(5) 0.64667(13) 1.05624(5) 0.0252(2) Uani 1 1 d . . .
O3 O 0.51878(5) 0.41144(14) 1.22625(4) 0.0220(2) Uani 1 1 d . . .
O4 O 0.60111(6) 0.28092(16) 1.32846(5) 0.0315(3) Uani 1 1 d . . .
O5 O 0.28242(5) 0.31570(16) 0.76379(5) 0.0293(2) Uani 1 1 d . . .
O6 O 0.16192(5) 0.39781(14) 0.68548(4) 0.0216(2) Uani 1 1 d . . .
O7 O 0.10453(5) 0.62538(13) 0.75377(5) 0.0252(2) Uani 1 1 d . . .
O8 O 0.10374(5) 0.44646(13) 0.84415(4) 0.0211(2) Uani 1 1 d . . .
N1 N 0.54600(6) 0.22692(15) 1.14191(5) 0.0172(2) Uani 1 1 d . . .
N2 N 0.34501(6) 0.36167(15) 1.04838(5) 0.0170(2) Uani 1 1 d . . .
N3 N 0.27816(6) 0.55113(15) 0.95474(5) 0.0194(2) Uani 1 1 d . . .
N4 N 0.23481(6) 0.09340(16) 0.86146(6) 0.0213(2) Uani 1 1 d . . .
N5 N 0.31447(6) 0.05938(15) 0.98767(6) 0.0206(2) Uani 1 1 d . . .
N6 N 0.19066(6) 0.38297(15) 0.80280(5) 0.0178(2) Uani 1 1 d . . .
C1 C 0.59496(8) 0.35118(19) 1.11969(7) 0.0237(3) Uani 1 1 d . . .
H1A H 0.6064 0.2886 1.0825 0.028 Uiso 1 1 calc R . .
H1B H 0.6441 0.3800 1.1612 0.028 Uiso 1 1 calc R . .
C2 C 0.54950(7) 0.52900(18) 1.09060(6) 0.0181(3) Uani 1 1 d . . .
C3 C 0.58831(8) 0.1513(2) 1.21613(7) 0.0237(3) Uani 1 1 d . . .
H3A H 0.6441 0.1456 1.2295 0.028 Uiso 1 1 calc R . .
H3B H 0.5700 0.0232 1.2198 0.028 Uiso 1 1 calc R . .
C4 C 0.57170(7) 0.2863(2) 1.26410(6) 0.0219(3) Uani 1 1 d . . .
C5 C 0.51233(9) 0.0718(2) 1.08904(7) 0.0279(3) Uani 1 1 d . . .
H5A H 0.5536 -0.0083 1.0887 0.042 Uiso 1 1 calc R . .
H5B H 0.4834 0.1254 1.0413 0.042 Uiso 1 1 calc R . .
H5C H 0.4778 -0.0037 1.1024 0.042 Uiso 1 1 calc R . .
C6 C 0.39660(7) 0.30873(19) 1.12226(6) 0.0190(3) Uani 1 1 d . . .
H6A H 0.3961 0.1700 1.1265 0.023 Uiso 1 1 calc R . .
H6B H 0.3761 0.3625 1.1548 0.023 Uiso 1 1 calc R . .
C7 C 0.32377(7) 0.54074(18) 1.02336(6) 0.0195(3) Uani 1 1 d . . .
H7A H 0.3406 0.6487 1.0532 0.023 Uiso 1 1 calc R . .
C8 C 0.26937(7) 0.36577(18) 0.93289(6) 0.0163(3) Uani 1 1 d . . .
C9 C 0.23204(7) 0.27899(18) 0.86726(6) 0.0169(3) Uani 1 1 d . . .
C10 C 0.27499(7) -0.00593(19) 0.92141(7) 0.0227(3) Uani 1 1 d . . .
H10A H 0.2753 -0.1386 0.9158 0.027 Uiso 1 1 calc R . .
C11 C 0.31027(7) 0.24577(18) 0.99053(6) 0.0156(3) Uani 1 1 d . . .
C12 C 0.21760(7) 0.36341(19) 0.74905(6) 0.0195(3) Uani 1 1 d . . .
C13 C 0.17648(8) 0.3885(2) 0.62010(7) 0.0255(3) Uani 1 1 d . . .
C14 C 0.23999(10) 0.5233(2) 0.62683(8) 0.0372(4) Uani 1 1 d . . .
H14A H 0.2277 0.6494 0.6382 0.056 Uiso 1 1 calc R . .
H14B H 0.2449 0.5273 0.5816 0.056 Uiso 1 1 calc R . .
H14C H 0.2885 0.4806 0.6651 0.056 Uiso 1 1 calc R . .
C15 C 0.09949(9) 0.4498(3) 0.56259(7) 0.0373(4) Uani 1 1 d . . .
H15A H 0.0875 0.5770 0.5732 0.056 Uiso 1 1 calc R . .
H15B H 0.0595 0.3625 0.5613 0.056 Uiso 1 1 calc R . .
H15C H 0.1016 0.4498 0.5161 0.056 Uiso 1 1 calc R . .
C16 C 0.19449(9) 0.1862(2) 0.60922(8) 0.0317(3) Uani 1 1 d . . .
H16A H 0.1522 0.1045 0.6064 0.048 Uiso 1 1 calc R . .
H16B H 0.2421 0.1469 0.6495 0.048 Uiso 1 1 calc R . .
H16C H 0.2008 0.1764 0.5647 0.048 Uiso 1 1 calc R . .
C17 C 0.12891(7) 0.49949(18) 0.79642(6) 0.0181(3) Uani 1 1 d . . .
C18 C 0.04828(8) 0.5669(2) 0.85846(7) 0.0250(3) Uani 1 1 d . . .
C19 C 0.03780(11) 0.4533(3) 0.91584(9) 0.0473(5) Uani 1 1 d . . .
H19A H 0.0875 0.4392 0.9573 0.071 Uiso 1 1 calc R . .
H19B H 0.0173 0.3288 0.8969 0.071 Uiso 1 1 calc R . .
H19C H 0.0019 0.5188 0.9303 0.071 Uiso 1 1 calc R . .
C20 C -0.02711(8) 0.5806(2) 0.79236(7) 0.0284(3) Uani 1 1 d . . .
H20A H -0.0194 0.6514 0.7552 0.043 Uiso 1 1 calc R . .
H20B H -0.0650 0.6455 0.8043 0.043 Uiso 1 1 calc R . .
H20C H -0.0457 0.4538 0.7748 0.043 Uiso 1 1 calc R . .
C21 C 0.08476(9) 0.7564(2) 0.88577(8) 0.0376(4) Uani 1 1 d . . .
H21A H 0.0930 0.8222 0.8479 0.056 Uiso 1 1 calc R . .
H21B H 0.1342 0.7384 0.9272 0.056 Uiso 1 1 calc R . .
H21C H 0.0508 0.8316 0.8999 0.056 Uiso 1 1 calc R . .
B1 B 0.48400(8) 0.3771(2) 1.14828(7) 0.0174(3) Uani 1 1 d . . .
O1W O 0.22845(7) 0.84114(17) 0.74888(6) 0.0382(3) Uani 1 1 d . . .
H1WA H 0.1790(15) 0.770(4) 0.7378(13) 0.083(8) Uiso 1 1 d . . .
H1WB H 0.2240(12) 0.935(3) 0.7815(11) 0.059(6) 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
O1 C2 1.3247(15) . ?
O1 B1 1.4597(17) . ?
O2 C2 1.2044(16) . ?
O3 C4 1.3268(17) . ?
O3 B1 1.4784(16) . ?
O4 C4 1.2041(16) . ?
O5 C12 1.2001(16) . ?
O6 C12 1.3172(15) . ?
O6 C13 1.4943(14) . ?
O7 C17 1.2019(16) . ?
O8 C17 1.3257(15) . ?
O8 C18 1.4927(15) . ?
N1 C5 1.4918(17) . ?
N1 C3 1.4971(15) . ?
N1 C1 1.4990(16) . ?
N1 B1 1.6473(17) . ?
N2 C7 1.3683(17) . ?
N2 C11 1.3688(16) . ?
N2 C6 1.4722(15) . ?
N3 C7 1.3142(17) . ?
N3 C8 1.3788(17) . ?
N4 C9 1.3268(17) . ?
N4 C10 1.3472(17) . ?
N5 C11 1.3293(17) . ?
N5 C10 1.3349(17) . ?
N6 C17 1.4078(16) . ?
N6 C12 1.4192(16) . ?
N6 C9 1.4322(15) . ?
C1 C2 1.5080(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.509(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 B1 1.6074(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9500 . ?
C8 C9 1.3806(17) . ?
C8 C11 1.4025(17) . ?
C10 H10A 0.9500 . ?
C13 C14 1.512(2) . ?
C13 C15 1.516(2) . ?
C13 C16 1.517(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C21 1.512(2) . ?
C18 C20 1.5141(19) . ?
C18 C19 1.517(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O1W H1WA 1.01(3) . ?
O1W H1WB 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 B1 113.99(10) . . ?
C4 O3 B1 114.18(10) . . ?
C12 O6 C13 120.50(10) . . ?
C17 O8 C18 120.24(10) . . ?
C5 N1 C3 111.24(11) . . ?
C5 N1 C1 110.13(10) . . ?
C3 N1 C1 112.77(10) . . ?
C5 N1 B1 115.70(10) . . ?
C3 N1 B1 104.28(9) . . ?
C1 N1 B1 102.41(9) . . ?
C7 N2 C11 105.83(10) . . ?
C7 N2 C6 126.18(10) . . ?
C11 N2 C6 127.96(11) . . ?
C7 N3 C8 103.43(10) . . ?
C9 N4 C10 117.81(11) . . ?
C11 N5 C10 111.90(11) . . ?
C17 N6 C12 124.05(10) . . ?
C17 N6 C9 120.19(10) . . ?
C12 N6 C9 115.73(10) . . ?
N1 C1 C2 106.36(10) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.6 . . ?
O2 C2 O1 124.13(12) . . ?
O2 C2 C1 125.13(12) . . ?
O1 C2 C1 110.73(10) . . ?
N1 C3 C4 105.68(10) . . ?
N1 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
N1 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
O4 C4 O3 123.67(13) . . ?
O4 C4 C3 125.05(13) . . ?
O3 C4 C3 111.26(10) . . ?
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 . . ?
N2 C6 B1 114.66(10) . . ?
N2 C6 H6A 108.6 . . ?
B1 C6 H6A 108.6 . . ?
N2 C6 H6B 108.6 . . ?
B1 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
N3 C7 N2 114.51(11) . . ?
N3 C7 H7A 122.7 . . ?
N2 C7 H7A 122.7 . . ?
N3 C8 C9 133.48(11) . . ?
N3 C8 C11 110.85(11) . . ?
C9 C8 C11 115.61(11) . . ?
N4 C9 C8 120.55(11) . . ?
N4 C9 N6 117.14(11) . . ?
C8 C9 N6 122.29(11) . . ?
N5 C10 N4 127.93(12) . . ?
N5 C10 H10A 116.0 . . ?
N4 C10 H10A 116.0 . . ?
N5 C11 N2 128.43(11) . . ?
N5 C11 C8 126.17(11) . . ?
N2 C11 C8 105.38(11) . . ?
O5 C12 O6 128.45(11) . . ?
O5 C12 N6 121.06(11) . . ?
O6 C12 N6 110.45(11) . . ?
O6 C13 C14 110.16(11) . . ?
O6 C13 C15 101.48(10) . . ?
C14 C13 C15 111.84(13) . . ?
O6 C13 C16 108.59(11) . . ?
C14 C13 C16 112.75(13) . . ?
C15 C13 C16 111.40(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O7 C17 O8 127.25(12) . . ?
O7 C17 N6 123.79(11) . . ?
O8 C17 N6 108.97(10) . . ?
O8 C18 C21 109.07(11) . . ?
O8 C18 C20 110.45(10) . . ?
C21 C18 C20 113.18(12) . . ?
O8 C18 C19 101.23(11) . . ?
C21 C18 C19 112.13(13) . . ?
C20 C18 C19 110.12(13) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 B1 O3 112.08(11) . . ?
O1 B1 C6 112.84(10) . . ?
O3 B1 C6 109.75(10) . . ?
O1 B1 N1 102.80(9) . . ?
O3 B1 N1 100.79(9) . . ?
C6 B1 N1 117.92(11) . . ?
H1WA O1W H1WB 98.3(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
C5 N1 C1 C2 104.97(12) . . . . ?
C3 N1 C1 C2 -130.12(11) . . . . ?
B1 N1 C1 C2 -18.64(12) . . . . ?
B1 O1 C2 O2 178.12(12) . . . . ?
B1 O1 C2 C1 -2.41(14) . . . . ?
N1 C1 C2 O2 -166.01(12) . . . . ?
N1 C1 C2 O1 14.53(14) . . . . ?
C5 N1 C3 C4 -141.86(11) . . . . ?
C1 N1 C3 C4 93.84(12) . . . . ?
B1 N1 C3 C4 -16.48(13) . . . . ?
B1 O3 C4 O4 -172.86(12) . . . . ?
B1 O3 C4 C3 5.84(15) . . . . ?
N1 C3 C4 O4 -173.35(12) . . . . ?
N1 C3 C4 O3 7.97(14) . . . . ?
C7 N2 C6 B1 -65.94(16) . . . . ?
C11 N2 C6 B1 112.09(14) . . . . ?
C8 N3 C7 N2 -0.62(14) . . . . ?
C11 N2 C7 N3 0.35(15) . . . . ?
C6 N2 C7 N3 178.73(11) . . . . ?
C7 N3 C8 C9 -176.41(14) . . . . ?
C7 N3 C8 C11 0.65(14) . . . . ?
C10 N4 C9 C8 0.02(18) . . . . ?
C10 N4 C9 N6 178.52(11) . . . . ?
N3 C8 C9 N4 178.16(13) . . . . ?
C11 C8 C9 N4 1.20(17) . . . . ?
N3 C8 C9 N6 -0.3(2) . . . . ?
C11 C8 C9 N6 -177.22(11) . . . . ?
C17 N6 C9 N4 122.31(13) . . . . ?
C12 N6 C9 N4 -59.38(15) . . . . ?
C17 N6 C9 C8 -59.22(16) . . . . ?
C12 N6 C9 C8 119.09(13) . . . . ?
C11 N5 C10 N4 0.65(19) . . . . ?
C9 N4 C10 N5 -1.1(2) . . . . ?
C10 N5 C11 N2 -177.81(12) . . . . ?
C10 N5 C11 C8 0.82(18) . . . . ?
C7 N2 C11 N5 178.95(12) . . . . ?
C6 N2 C11 N5 0.6(2) . . . . ?
C7 N2 C11 C8 0.09(13) . . . . ?
C6 N2 C11 C8 -178.26(11) . . . . ?
N3 C8 C11 N5 -179.36(11) . . . . ?
C9 C8 C11 N5 -1.72(18) . . . . ?
N3 C8 C11 N2 -0.47(13) . . . . ?
C9 C8 C11 N2 177.17(10) . . . . ?
C13 O6 C12 O5 -3.1(2) . . . . ?
C13 O6 C12 N6 179.24(11) . . . . ?
C17 N6 C12 O5 155.50(13) . . . . ?
C9 N6 C12 O5 -22.73(18) . . . . ?
C17 N6 C12 O6 -26.65(17) . . . . ?
C9 N6 C12 O6 155.12(11) . . . . ?
C12 O6 C13 C14 -57.76(17) . . . . ?
C12 O6 C13 C15 -176.37(12) . . . . ?
C12 O6 C13 C16 66.18(15) . . . . ?
C18 O8 C17 O7 -11.31(19) . . . . ?
C18 O8 C17 N6 168.76(10) . . . . ?
C12 N6 C17 O7 -18.15(19) . . . . ?
C9 N6 C17 O7 160.01(12) . . . . ?
C12 N6 C17 O8 161.78(11) . . . . ?
C9 N6 C17 O8 -20.06(15) . . . . ?
C17 O8 C18 C21 -60.79(15) . . . . ?
C17 O8 C18 C20 64.20(16) . . . . ?
C17 O8 C18 C19 -179.15(13) . . . . ?
C2 O1 B1 O3 97.96(12) . . . . ?
C2 O1 B1 C6 -137.53(11) . . . . ?
C2 O1 B1 N1 -9.45(13) . . . . ?
C4 O3 B1 O1 -124.22(11) . . . . ?
C4 O3 B1 C6 109.58(12) . . . . ?
C4 O3 B1 N1 -15.51(13) . . . . ?
N2 C6 B1 O1 24.08(15) . . . . ?
N2 C6 B1 O3 149.85(11) . . . . ?
N2 C6 B1 N1 -95.61(13) . . . . ?
C5 N1 B1 O1 -102.65(12) . . . . ?
C3 N1 B1 O1 134.85(10) . . . . ?
C1 N1 B1 O1 17.15(11) . . . . ?
C5 N1 B1 O3 141.52(10) . . . . ?
C3 N1 B1 O3 19.01(12) . . . . ?
C1 N1 B1 O3 -98.69(10) . . . . ?
C5 N1 B1 C6 22.16(15) . . . . ?
C3 N1 B1 C6 -100.34(12) . . . . ?
C1 N1 B1 C6 141.96(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
O1W H1WA O7 1.01(3) 1.90(3) 2.8729(15) 159(2) .
O1W H1WB N4 0.98(2) 1.94(2) 2.8981(15) 167.5(19) 1_565

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        66.47
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047


