# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cmpd_4a
_database_code_depnum_ccdc_archive 'CCDC 1964346'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_cmpd_4a             
;
PROBLEM: D-H Without Acceptor       O5     --  H12    ...     Please Check 
RESPONSE: The hydrogen position of H12 was checked, and there is indeed the 
electron density found, and the hydrogen atom could also be freely refined 
without significant changes on the atom position.
;

_audit_creation_date             2017-05-11


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C11 H16 B3 N O7'
_chemical_formula_sum            'C11 H16 B3 N O7'
_chemical_formula_weight         306.68

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

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

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

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

_cell_length_a                   8.430(6)
_cell_length_b                   17.184(13)
_cell_length_c                   9.073(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.26(4)
_cell_angle_gamma                90
_cell_volume                     1312.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2935
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.97
_cell_special_details            
;
To simulate systematic errors the final estimation of uncertainties
in unit cell parameters was based on 32 Monte-Carlo simulations.
;


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 700).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_T_max  0.7453
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -2.00 1.00 0.0740
2.00 -3.00 0.00 0.0670
-1.00 3.00 -1.00 0.0430
0.00 3.00 -2.00 0.0340
0.00 -3.00 2.00 0.1230
1.00 -3.00 1.00 0.0740
-1.00 2.00 0.00 0.1040
1.00 -2.00 0.00 0.0680
0.00 -2.00 1.00 0.1120
0.00 3.00 -1.00 0.0330
0.00 -3.00 1.00 0.0980
1.00 2.00 -1.00 0.0570
1.00 4.00 1.00 0.0350
-1.00 -4.00 0.00 0.0660
-3.00 2.00 2.00 0.1800
-2.00 4.00 1.00 0.1330
-1.00 1.00 0.00 0.1090
0.00 1.00 2.00 0.1460
-1.00 -4.00 -4.00 0.0330
-1.00 -3.00 -1.00 0.0050
1.00 3.00 1.00 0.0360

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10207
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         26.057
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2587
_reflns_number_gt                1992
_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       'APEX3 ver. 2016.1-0 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0554P)²+0.8515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         2587
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.23684(17) 0.49924(8) 0.39682(16) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.1925(2) 0.56568(12) 0.4633(2) 0.0231(5) Uani 1 1 d . . . . .
N1 N 0.48378(19) 0.64077(10) 0.25848(19) 0.0216(4) Uani 1 1 d . . . . .
H1 H 0.5383 0.6113 0.1808 0.026 Uiso 1 1 calc R U . . .
B1 B 0.2957(3) 0.51729(14) 0.2499(3) 0.0219(5) Uani 1 1 d . . . . .
B2 B 0.2163(3) 0.45029(14) 0.0131(3) 0.0228(5) Uani 1 1 d . . . . .
O2 O 0.17713(15) 0.49202(8) 0.13135(15) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.1186(2) 0.56716(13) 0.5967(2) 0.0262(5) Uani 1 1 d . . . . .
H2 H 0.0996 0.5205 0.6489 0.031 Uiso 1 1 calc R U . . .
O3 O 0.36994(17) 0.42023(8) 0.00414(16) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.0734(2) 0.63864(14) 0.6512(2) 0.0283(5) Uani 1 1 d . . . . .
H3 H 0.0235 0.6408 0.7424 0.034 Uiso 1 1 calc R U . . .
B3 B 0.4792(3) 0.43157(14) 0.1215(3) 0.0225(5) Uani 1 1 d . . . . .
O4 O 0.44801(16) 0.47692(8) 0.23622(16) 0.0245(4) Uani 1 1 d . . . . .
C4 C 0.0995(2) 0.70739(13) 0.5748(2) 0.0273(5) Uani 1 1 d . . . . .
H4 H 0.0660 0.7558 0.6131 0.033 Uiso 1 1 calc R U . . .
O5 O 0.62144(18) 0.39394(9) 0.11118(18) 0.0288(4) Uani 1 1 d . . . . .
H12 H 0.682(2) 0.4047(13) 0.186(3) 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1747(2) 0.70504(13) 0.4427(2) 0.0238(5) Uani 1 1 d . . . . .
H5 H 0.1919 0.7518 0.3900 0.029 Uiso 1 1 calc R U . . .
O7 O 0.74449(17) 0.73435(9) 0.37509(18) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.3106(2) 0.61350(12) 0.2509(2) 0.0211(5) Uani 1 1 d . . . . .
H7 H 0.2526 0.6356 0.1613 0.025 Uiso 1 1 calc R U . . .
O6 O 0.11424(19) 0.43405(10) -0.10393(17) 0.0326(4) Uani 1 1 d . . . . .
H6 H 0.024(3) 0.4525(16) -0.0888(15) 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2250(2) 0.63431(12) 0.3873(2) 0.0211(5) Uani 1 1 d . . . . .
C8 C 0.4994(2) 0.72531(12) 0.2227(3) 0.0249(5) Uani 1 1 d . . . . .
H8A H 0.4394 0.7566 0.2924 0.030 Uiso 1 1 calc R U . . .
H8B H 0.4535 0.7353 0.1216 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6730(3) 0.74992(14) 0.2332(3) 0.0299(5) Uani 1 1 d . . . . .
H9A H 0.7311 0.7216 0.1580 0.036 Uiso 1 1 calc R U . . .
H9B H 0.6805 0.8063 0.2121 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7409(3) 0.65239(13) 0.4010(3) 0.0293(5) Uani 1 1 d . . . . .
H10A H 0.7981 0.6406 0.4967 0.035 Uiso 1 1 calc R U . . .
H10B H 0.7961 0.6252 0.3225 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5716(2) 0.62290(13) 0.4031(2) 0.0245(5) Uani 1 1 d . . . . .
H11A H 0.5720 0.5660 0.4203 0.029 Uiso 1 1 calc R U . . .
H11B H 0.5175 0.6481 0.4845 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.354(3) . ?
O1 B1 1.481(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.401(3) . ?
N1 C8 1.496(3) . ?
N1 C11 1.501(3) . ?
N1 C7 1.531(3) . ?
N1 H1 1.0000 . ?
B1 O4 1.471(3) . ?
B1 O2 1.491(3) . ?
B1 C7 1.658(3) . ?
B2 O2 1.347(3) . ?
B2 O6 1.357(3) . ?
B2 O3 1.401(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
O3 B3 1.381(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
B3 O4 1.339(3) . ?
B3 O5 1.371(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
O5 H12 0.85(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
O7 C9 1.416(3) . ?
O7 C10 1.428(3) . ?
C7 C6 1.511(3) . ?
C7 H7 1.0000 . ?
O6 H6 0.84(3) . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 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
C1 O1 B1 109.86(17) . . ?
O1 C1 C2 123.5(2) . . ?
O1 C1 C6 115.08(19) . . ?
C2 C1 C6 121.5(2) . . ?
C8 N1 C11 110.06(16) . . ?
C8 N1 C7 112.52(15) . . ?
C11 N1 C7 113.47(16) . . ?
C8 N1 H1 106.8 . . ?
C11 N1 H1 106.8 . . ?
C7 N1 H1 106.8 . . ?
O4 B1 O1 108.42(17) . . ?
O4 B1 O2 110.76(18) . . ?
O1 B1 O2 110.05(17) . . ?
O4 B1 C7 113.87(17) . . ?
O1 B1 C7 103.47(17) . . ?
O2 B1 C7 109.99(17) . . ?
O2 B2 O6 124.0(2) . . ?
O2 B2 O3 120.80(19) . . ?
O6 B2 O3 115.2(2) . . ?
B2 O2 B1 123.01(17) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
B3 O3 B2 118.76(18) . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
O4 B3 O5 122.6(2) . . ?
O4 B3 O3 122.0(2) . . ?
O5 B3 O3 115.4(2) . . ?
B3 O4 B1 123.44(17) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
B3 O5 H12 109.5 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C9 O7 C10 108.92(17) . . ?
C6 C7 N1 112.94(16) . . ?
C6 C7 B1 101.59(17) . . ?
N1 C7 B1 112.16(16) . . ?
C6 C7 H7 110.0 . . ?
N1 C7 H7 110.0 . . ?
B1 C7 H7 110.0 . . ?
B2 O6 H6 109.5 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 132.3(2) . . ?
C1 C6 C7 108.65(18) . . ?
N1 C8 C9 110.66(17) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O7 C9 C8 111.24(18) . . ?
O7 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O7 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O7 C10 C11 111.12(17) . . ?
O7 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
O7 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N1 C11 C10 109.80(18) . . ?
N1 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?

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
B1 O1 C1 C2 173.86(19) . . . . ?
B1 O1 C1 C6 -5.5(2) . . . . ?
C1 O1 B1 O4 131.59(17) . . . . ?
C1 O1 B1 O2 -107.12(18) . . . . ?
C1 O1 B1 C7 10.4(2) . . . . ?
O6 B2 O2 B1 -172.4(2) . . . . ?
O3 B2 O2 B1 7.7(3) . . . . ?
O4 B1 O2 B2 -12.2(3) . . . . ?
O1 B1 O2 B2 -132.1(2) . . . . ?
C7 B1 O2 B2 114.5(2) . . . . ?
O1 C1 C2 C3 -177.60(18) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
O2 B2 O3 B3 2.5(3) . . . . ?
O6 B2 O3 B3 -177.47(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
B2 O3 B3 O4 -7.0(3) . . . . ?
B2 O3 B3 O5 173.69(18) . . . . ?
O5 B3 O4 B1 -179.50(19) . . . . ?
O3 B3 O4 B1 1.2(3) . . . . ?
O1 B1 O4 B3 128.7(2) . . . . ?
O2 B1 O4 B3 7.8(3) . . . . ?
C7 B1 O4 B3 -116.8(2) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C8 N1 C7 C6 -79.9(2) . . . . ?
C11 N1 C7 C6 45.9(2) . . . . ?
C8 N1 C7 B1 166.04(18) . . . . ?
C11 N1 C7 B1 -68.2(2) . . . . ?
O4 B1 C7 C6 -128.67(18) . . . . ?
O1 B1 C7 C6 -11.19(19) . . . . ?
O2 B1 C7 C6 106.35(19) . . . . ?
O4 B1 C7 N1 -7.8(3) . . . . ?
O1 B1 C7 N1 109.68(18) . . . . ?
O2 B1 C7 N1 -132.78(17) . . . . ?
C4 C5 C6 C1 2.7(3) . . . . ?
C4 C5 C6 C7 -178.85(19) . . . . ?
O1 C1 C6 C5 176.04(17) . . . . ?
C2 C1 C6 C5 -3.3(3) . . . . ?
O1 C1 C6 C7 -2.8(2) . . . . ?
C2 C1 C6 C7 177.86(18) . . . . ?
N1 C7 C6 C5 69.7(3) . . . . ?
B1 C7 C6 C5 -170.0(2) . . . . ?
N1 C7 C6 C1 -111.73(18) . . . . ?
B1 C7 C6 C1 8.6(2) . . . . ?
C11 N1 C8 C9 51.8(2) . . . . ?
C7 N1 C8 C9 179.42(17) . . . . ?
C10 O7 C9 C8 62.3(2) . . . . ?
N1 C8 C9 O7 -57.4(2) . . . . ?
C9 O7 C10 C11 -63.4(2) . . . . ?
C8 N1 C11 C10 -52.5(2) . . . . ?
C7 N1 C11 C10 -179.58(16) . . . . ?
O7 C10 C11 N1 58.9(2) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.053


_chemical_name_systematic        
4',6'-dihydroxy-3-(morpholino-4-ium)-3H-spiro[benzo[d][1,2]oxaborole-2,2'-[1,3,5,2,4,6]trioxatriborinan]-2-uide
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/toluene'
####################################################################### 
# 
# 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_cmpd_4d
_database_code_depnum_ccdc_archive 'CCDC 1964347'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(dibenzylammonio)-4',6'-dihydroxy-3H-spiro[benzo[d][1,2]oxaborole-2,2'-[1,3,5,2,4,6]trioxatriborinan]-2-uide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 B3 N O6, 2(C3 H6 O)'
_chemical_formula_sum            'C27 H34 B3 N O8'
_chemical_formula_weight         532.98

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                   9.549(5)
_cell_length_b                   11.307(2)
_cell_length_c                   13.260(3)
_cell_angle_alpha                100.88(3)
_cell_angle_beta                 92.261(11)
_cell_angle_gamma                105.79(3)
_cell_volume                     1346.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4684
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.35


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
glass fiber and transferred to stream of cold nitrogen.
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.155
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5848
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            15073
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.571
_diffrn_reflns_theta_max         26.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5534
_reflns_number_gt                4451
_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       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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.
Due to disorder of solventmolecule aceton the displacement parameters of atoms 
C1_1, C2_1, C3_1, O4_1, C1_11, C2_11, C3_11 and O4_11 of the residue 1 were 
restrained to the same value with similarity restraint SIMU. Furthermore, their
Uii displacement parameters were restrained with ISOR keyword to approximate 
isotropic behavior. The 1-2 and 1-3 distances in AC residues were restrained to 
the same values with SAME. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5534
_refine_ls_number_parameters     399
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1_1 C 0.632(2) -0.0636(11) 0.5402(12) 0.0210(10) Uani 0.43(2) 1 d D U P A 1
C2_1 C 0.7338(13) -0.0200(11) 0.4640(9) 0.0296(17) Uani 0.43(2) 1 d D U P A 1
H2A_1 H 0.6835 -0.0508 0.3943 0.044 Uiso 0.43(2) 1 calc R U P A 1
H2B_1 H 0.8186 -0.0524 0.4688 0.044 Uiso 0.43(2) 1 calc R U P A 1
H2C_1 H 0.7666 0.0721 0.4789 0.044 Uiso 0.43(2) 1 calc R U P A 1
C3_1 C 0.5531(14) -0.2008(9) 0.5219(8) 0.0231(14) Uani 0.43(2) 1 d D U P A 1
H3A_1 H 0.5162 -0.2317 0.4490 0.035 Uiso 0.43(2) 1 calc R U P A 1
H3B_1 H 0.4710 -0.2140 0.5646 0.035 Uiso 0.43(2) 1 calc R U P A 1
H3C_1 H 0.6206 -0.2467 0.5402 0.035 Uiso 0.43(2) 1 calc R U P A 1
O4_1 O 0.6012(17) 0.0096(17) 0.6103(14) 0.0240(15) Uani 0.43(2) 1 d D U P A 1
C1_11 C 0.6408(15) -0.0531(8) 0.5347(9) 0.0205(9) Uani 0.57(2) 1 d D U P A 2
C2_11 C 0.7190(9) -0.0022(8) 0.4496(7) 0.0252(13) Uani 0.57(2) 1 d D U P A 2
H2A_11 H 0.6620 -0.0446 0.3832 0.038 Uiso 0.57(2) 1 calc R U P A 2
H2B_11 H 0.8154 -0.0170 0.4494 0.038 Uiso 0.57(2) 1 calc R U P A 2
H2C_11 H 0.7307 0.0882 0.4603 0.038 Uiso 0.57(2) 1 calc R U P A 2
C3_11 C 0.5970(12) -0.1929(7) 0.5229(6) 0.0263(11) Uani 0.57(2) 1 d D U P A 2
H3A_11 H 0.5323 -0.2319 0.4591 0.039 Uiso 0.57(2) 1 calc R U P A 2
H3B_11 H 0.5455 -0.2159 0.5820 0.039 Uiso 0.57(2) 1 calc R U P A 2
H3C_11 H 0.6844 -0.2225 0.5199 0.039 Uiso 0.57(2) 1 calc R U P A 2
O4_11 O 0.6225(13) 0.0151(13) 0.6129(10) 0.0245(12) Uani 0.57(2) 1 d D U P A 2
C1_2 C 0.45381(17) 0.77249(14) 0.78324(11) 0.0204(3) Uani 1 1 d D . . . .
C2_2 C 0.5863(2) 0.86777(15) 0.84137(13) 0.0312(4) Uani 1 1 d D . . . .
H2A_2 H 0.6626 0.8271 0.8518 0.047 Uiso 1 1 calc R U . . .
H2B_2 H 0.5613 0.9055 0.9085 0.047 Uiso 1 1 calc R U . . .
H2C_2 H 0.6220 0.9333 0.8020 0.047 Uiso 1 1 calc R U . . .
C3_2 C 0.3242(2) 0.81681(16) 0.76088(14) 0.0321(4) Uani 1 1 d D . . . .
H3A_2 H 0.3574 0.9022 0.7481 0.048 Uiso 1 1 calc R U . . .
H3B_2 H 0.2660 0.8168 0.8201 0.048 Uiso 1 1 calc R U . . .
H3C_2 H 0.2642 0.7605 0.6998 0.048 Uiso 1 1 calc R U . . .
O4_2 O 0.45089(12) 0.66272(9) 0.75543(8) 0.0238(3) Uani 1 1 d D . . . .
C1_3 C 0.16401(16) 0.57845(12) 0.92109(10) 0.0140(3) Uani 1 1 d . . . . .
C2_3 C 0.04281(16) 0.62441(13) 0.92112(11) 0.0152(3) Uani 1 1 d . . . . .
H2_3 H -0.0467 0.5741 0.8830 0.018 Uiso 1 1 calc R U . . .
C3_3 C 0.05278(16) 0.74391(13) 0.97697(11) 0.0172(3) Uani 1 1 d . . . . .
H3_3 H -0.0300 0.7752 0.9769 0.021 Uiso 1 1 calc R U . . .
C4_3 C 0.18272(17) 0.81746(13) 1.03270(11) 0.0184(3) Uani 1 1 d . . . . .
H4_3 H 0.1885 0.8987 1.0714 0.022 Uiso 1 1 calc R U . . .
C5_3 C 0.30503(17) 0.77318(13) 1.03232(11) 0.0179(3) Uani 1 1 d . . . . .
H5_3 H 0.3945 0.8242 1.0700 0.022 Uiso 1 1 calc R U . . .
C6_3 C 0.29562(16) 0.65389(13) 0.97649(10) 0.0152(3) Uani 1 1 d . . . . .
H6_3 H 0.3790 0.6234 0.9759 0.018 Uiso 1 1 calc R U . . .
C7_3 C 0.15210(16) 0.44456(12) 0.86971(10) 0.0142(3) Uani 1 1 d . . . . .
H7A_3 H 0.0484 0.3942 0.8628 0.017 Uiso 1 1 calc R U . . .
H7AB_3 H 0.2082 0.4091 0.9144 0.017 Uiso 1 1 calc R U . . .
C1_4 C 0.12943(16) 0.42029(13) 0.57575(11) 0.0166(3) Uani 1 1 d . . . . .
C2_4 C 0.02781(18) 0.32697(14) 0.50513(12) 0.0213(3) Uani 1 1 d . . . . .
H2_4 H -0.0598 0.2808 0.5277 0.026 Uiso 1 1 calc R U . . .
C3_4 C 0.05279(18) 0.30032(14) 0.40191(12) 0.0236(4) Uani 1 1 d . . . . .
H3_4 H -0.0171 0.2356 0.3546 0.028 Uiso 1 1 calc R U . . .
C4_4 C 0.1791(2) 0.36771(14) 0.36787(12) 0.0254(4) Uani 1 1 d . . . . .
H4_4 H 0.1960 0.3499 0.2972 0.030 Uiso 1 1 calc R U . . .
C5_4 C 0.28093(19) 0.46148(14) 0.43765(12) 0.0251(4) Uani 1 1 d . . . . .
H5_4 H 0.3679 0.5082 0.4147 0.030 Uiso 1 1 calc R U . . .
C6_4 C 0.25613(18) 0.48732(13) 0.54102(11) 0.0212(3) Uani 1 1 d . . . . .
H6_4 H 0.3266 0.5515 0.5884 0.025 Uiso 1 1 calc R U . . .
C7_4 C 0.09546(16) 0.44584(13) 0.68661(11) 0.0164(3) Uani 1 1 d . . . . .
H7A_4 H -0.0002 0.3871 0.6930 0.020 Uiso 1 1 calc R U . . .
H7AB_4 H 0.0859 0.5322 0.7044 0.020 Uiso 1 1 calc R U . . .
C1_5 C 0.25860(16) 0.31438(12) 0.73681(11) 0.0138(3) Uani 1 1 d . . . . .
H1_5 H 0.2759 0.2987 0.6622 0.017 Uiso 1 1 calc R U . . .
C2_5 C 0.15428(15) 0.19858(12) 0.76049(10) 0.0135(3) Uani 1 1 d . . . . .
C3_5 C 0.21838(16) 0.16292(12) 0.84223(11) 0.0144(3) Uani 1 1 d . . . . .
C4_5 C 0.14943(17) 0.05471(13) 0.87597(11) 0.0180(3) Uani 1 1 d . . . . .
H4_5 H 0.1929 0.0317 0.9322 0.022 Uiso 1 1 calc R U . . .
C5_5 C 0.01510(17) -0.01930(13) 0.82535(12) 0.0203(3) Uani 1 1 d . . . . .
H5_5 H -0.0333 -0.0942 0.8471 0.024 Uiso 1 1 calc R U . . .
C6_5 C -0.04955(17) 0.01405(13) 0.74378(12) 0.0203(3) Uani 1 1 d . . . . .
H6_5 H -0.1414 -0.0379 0.7101 0.024 Uiso 1 1 calc R U . . .
C7_5 C 0.02005(16) 0.12372(12) 0.71108(11) 0.0166(3) Uani 1 1 d . . . . .
H7_5 H -0.0242 0.1470 0.6554 0.020 Uiso 1 1 calc R U . . .
B8_5 B 0.40919(18) 0.32490(14) 0.80855(12) 0.0147(3) Uani 1 1 d . . . . .
B9_5 B 0.62436(18) 0.50914(14) 0.86184(12) 0.0148(3) Uani 1 1 d . . . . .
B10_5 B 0.64847(19) 0.32952(15) 0.74418(12) 0.0159(3) Uani 1 1 d . . . . .
O11_5 O 0.48142(11) 0.45095(9) 0.86741(7) 0.0152(2) Uani 1 1 d . . . . .
O12_5 O 0.69655(11) 0.62475(9) 0.91979(8) 0.0179(2) Uani 1 1 d . . . . .
H12_5 H 0.6439(14) 0.6464(9) 0.9651(13) 0.027 Uiso 1 1 calc R U . . .
O13_5 O 0.70864(11) 0.45265(9) 0.79711(7) 0.0177(2) Uani 1 1 d . . . . .
O14_5 O 0.74036(12) 0.27353(10) 0.68967(8) 0.0218(2) Uani 1 1 d . . . . .
H14_5 H 0.6916(12) 0.1912(18) 0.6617(13) 0.033 Uiso 1 1 calc R U . . .
O15_5 O 0.50616(11) 0.26908(9) 0.74537(7) 0.0163(2) Uani 1 1 d . . . . .
O16_5 O 0.35131(11) 0.24096(8) 0.88402(7) 0.0154(2) Uani 1 1 d . . . . .
N17_5 N 0.20841(13) 0.43288(10) 0.76384(9) 0.0132(3) Uani 1 1 d . . . . .
H17_5 H 0.2968 0.5062 0.7680 0.016 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1_1 O4_1 1.223(10) . ?
C1_1 C2_1 1.490(10) . ?
C1_1 C3_1 1.496(10) . ?
C2_1 H2A_1 0.9800 . ?
C2_1 H2B_1 0.9800 . ?
C2_1 H2C_1 0.9800 . ?
C3_1 H3A_1 0.9800 . ?
C3_1 H3B_1 0.9800 . ?
C3_1 H3C_1 0.9800 . ?
C1_11 O4_11 1.219(8) . ?
C1_11 C2_11 1.497(8) . ?
C1_11 C3_11 1.497(8) . ?
C2_11 H2A_11 0.9800 . ?
C2_11 H2B_11 0.9800 . ?
C2_11 H2C_11 0.9800 . ?
C3_11 H3A_11 0.9800 . ?
C3_11 H3B_11 0.9800 . ?
C3_11 H3C_11 0.9800 . ?
C1_2 O4_2 1.2185(18) . ?
C1_2 C2_2 1.491(2) . ?
C1_2 C3_2 1.496(2) . ?
C2_2 H2A_2 0.9800 . ?
C2_2 H2B_2 0.9800 . ?
C2_2 H2C_2 0.9800 . ?
C3_2 H3A_2 0.9800 . ?
C3_2 H3B_2 0.9800 . ?
C3_2 H3C_2 0.9800 . ?
C1_3 C2_3 1.392(2) . ?
C1_3 C6_3 1.398(2) . ?
C1_3 C7_3 1.5099(18) . ?
C2_3 C3_3 1.3893(19) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.382(2) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.390(2) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.3883(19) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
C7_3 N17_5 1.5184(17) . ?
C7_3 H7A_3 0.9900 . ?
C7_3 H7AB_3 0.9900 . ?
C1_4 C6_4 1.388(2) . ?
C1_4 C2_4 1.389(2) . ?
C1_4 C7_4 1.5092(19) . ?
C2_4 C3_4 1.389(2) . ?
C2_4 H2_4 0.9500 . ?
C3_4 C4_4 1.383(2) . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.387(2) . ?
C4_4 H4_4 0.9500 . ?
C5_4 C6_4 1.390(2) . ?
C5_4 H5_4 0.9500 . ?
C6_4 H6_4 0.9500 . ?
C7_4 N17_5 1.5130(19) . ?
C7_4 H7A_4 0.9900 . ?
C7_4 H7AB_4 0.9900 . ?
C1_5 C2_5 1.508(2) . ?
C1_5 N17_5 1.5282(17) . ?
C1_5 B8_5 1.656(2) . ?
C1_5 H1_5 1.0000 . ?
C2_5 C7_5 1.387(2) . ?
C2_5 C3_5 1.400(2) . ?
C3_5 O16_5 1.3592(18) . ?
C3_5 C4_5 1.386(2) . ?
C4_5 C5_5 1.390(2) . ?
C4_5 H4_5 0.9500 . ?
C5_5 C6_5 1.386(2) . ?
C5_5 H5_5 0.9500 . ?
C6_5 C7_5 1.394(2) . ?
C6_5 H6_5 0.9500 . ?
C7_5 H7_5 0.9500 . ?
B8_5 O11_5 1.4556(18) . ?
B8_5 O15_5 1.4620(18) . ?
B8_5 O16_5 1.5246(19) . ?
B9_5 O11_5 1.356(2) . ?
B9_5 O12_5 1.3649(19) . ?
B9_5 O13_5 1.3855(19) . ?
B10_5 O15_5 1.347(2) . ?
B10_5 O14_5 1.3686(19) . ?
B10_5 O13_5 1.3875(19) . ?
O12_5 H12_5 0.842(19) . ?
O14_5 H14_5 0.917(19) . ?
N17_5 H17_5 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4_1 C1_1 C2_1 122.2(11) . . ?
O4_1 C1_1 C3_1 119.8(11) . . ?
C2_1 C1_1 C3_1 117.6(9) . . ?
C1_1 C2_1 H2A_1 109.5 . . ?
C1_1 C2_1 H2B_1 109.5 . . ?
H2A_1 C2_1 H2B_1 109.5 . . ?
C1_1 C2_1 H2C_1 109.5 . . ?
H2A_1 C2_1 H2C_1 109.5 . . ?
H2B_1 C2_1 H2C_1 109.5 . . ?
C1_1 C3_1 H3A_1 109.5 . . ?
C1_1 C3_1 H3B_1 109.5 . . ?
H3A_1 C3_1 H3B_1 109.5 . . ?
C1_1 C3_1 H3C_1 109.5 . . ?
H3A_1 C3_1 H3C_1 109.5 . . ?
H3B_1 C3_1 H3C_1 109.5 . . ?
O4_11 C1_11 C2_11 122.3(9) . . ?
O4_11 C1_11 C3_11 121.3(9) . . ?
C2_11 C1_11 C3_11 116.3(6) . . ?
C1_11 C2_11 H2A_11 109.5 . . ?
C1_11 C2_11 H2B_11 109.5 . . ?
H2A_11 C2_11 H2B_11 109.5 . . ?
C1_11 C2_11 H2C_11 109.5 . . ?
H2A_11 C2_11 H2C_11 109.5 . . ?
H2B_11 C2_11 H2C_11 109.5 . . ?
C1_11 C3_11 H3A_11 109.5 . . ?
C1_11 C3_11 H3B_11 109.5 . . ?
H3A_11 C3_11 H3B_11 109.5 . . ?
C1_11 C3_11 H3C_11 109.5 . . ?
H3A_11 C3_11 H3C_11 109.5 . . ?
H3B_11 C3_11 H3C_11 109.5 . . ?
O4_2 C1_2 C2_2 121.39(16) . . ?
O4_2 C1_2 C3_2 121.25(15) . . ?
C2_2 C1_2 C3_2 117.36(14) . . ?
C1_2 C2_2 H2A_2 109.5 . . ?
C1_2 C2_2 H2B_2 109.5 . . ?
H2A_2 C2_2 H2B_2 109.5 . . ?
C1_2 C2_2 H2C_2 109.5 . . ?
H2A_2 C2_2 H2C_2 109.5 . . ?
H2B_2 C2_2 H2C_2 109.5 . . ?
C1_2 C3_2 H3A_2 109.5 . . ?
C1_2 C3_2 H3B_2 109.5 . . ?
H3A_2 C3_2 H3B_2 109.5 . . ?
C1_2 C3_2 H3C_2 109.5 . . ?
H3A_2 C3_2 H3C_2 109.5 . . ?
H3B_2 C3_2 H3C_2 109.5 . . ?
C2_3 C1_3 C6_3 119.53(13) . . ?
C2_3 C1_3 C7_3 120.94(13) . . ?
C6_3 C1_3 C7_3 119.33(13) . . ?
C3_3 C2_3 C1_3 119.96(14) . . ?
C3_3 C2_3 H2_3 120.0 . . ?
C1_3 C2_3 H2_3 120.0 . . ?
C4_3 C3_3 C2_3 120.25(14) . . ?
C4_3 C3_3 H3_3 119.9 . . ?
C2_3 C3_3 H3_3 119.9 . . ?
C3_3 C4_3 C5_3 120.34(13) . . ?
C3_3 C4_3 H4_3 119.8 . . ?
C5_3 C4_3 H4_3 119.8 . . ?
C6_3 C5_3 C4_3 119.61(14) . . ?
C6_3 C5_3 H5_3 120.2 . . ?
C4_3 C5_3 H5_3 120.2 . . ?
C5_3 C6_3 C1_3 120.32(14) . . ?
C5_3 C6_3 H6_3 119.8 . . ?
C1_3 C6_3 H6_3 119.8 . . ?
C1_3 C7_3 N17_5 113.19(11) . . ?
C1_3 C7_3 H7A_3 108.9 . . ?
N17_5 C7_3 H7A_3 108.9 . . ?
C1_3 C7_3 H7AB_3 108.9 . . ?
N17_5 C7_3 H7AB_3 108.9 . . ?
H7A_3 C7_3 H7AB_3 107.8 . . ?
C6_4 C1_4 C2_4 118.68(14) . . ?
C6_4 C1_4 C7_4 122.96(13) . . ?
C2_4 C1_4 C7_4 118.34(13) . . ?
C1_4 C2_4 C3_4 120.78(15) . . ?
C1_4 C2_4 H2_4 119.6 . . ?
C3_4 C2_4 H2_4 119.6 . . ?
C4_4 C3_4 C2_4 120.19(14) . . ?
C4_4 C3_4 H3_4 119.9 . . ?
C2_4 C3_4 H3_4 119.9 . . ?
C3_4 C4_4 C5_4 119.48(15) . . ?
C3_4 C4_4 H4_4 120.3 . . ?
C5_4 C4_4 H4_4 120.3 . . ?
C4_4 C5_4 C6_4 120.20(15) . . ?
C4_4 C5_4 H5_4 119.9 . . ?
C6_4 C5_4 H5_4 119.9 . . ?
C1_4 C6_4 C5_4 120.67(14) . . ?
C1_4 C6_4 H6_4 119.7 . . ?
C5_4 C6_4 H6_4 119.7 . . ?
C1_4 C7_4 N17_5 114.60(12) . . ?
C1_4 C7_4 H7A_4 108.6 . . ?
N17_5 C7_4 H7A_4 108.6 . . ?
C1_4 C7_4 H7AB_4 108.6 . . ?
N17_5 C7_4 H7AB_4 108.6 . . ?
H7A_4 C7_4 H7AB_4 107.6 . . ?
C2_5 C1_5 N17_5 114.14(11) . . ?
C2_5 C1_5 B8_5 101.48(12) . . ?
N17_5 C1_5 B8_5 112.01(11) . . ?
C2_5 C1_5 H1_5 109.6 . . ?
N17_5 C1_5 H1_5 109.6 . . ?
B8_5 C1_5 H1_5 109.6 . . ?
C7_5 C2_5 C3_5 119.62(13) . . ?
C7_5 C2_5 C1_5 130.98(14) . . ?
C3_5 C2_5 C1_5 109.19(13) . . ?
O16_5 C3_5 C4_5 123.55(14) . . ?
O16_5 C3_5 C2_5 115.13(12) . . ?
C4_5 C3_5 C2_5 121.32(14) . . ?
C3_5 C4_5 C5_5 118.24(14) . . ?
C3_5 C4_5 H4_5 120.9 . . ?
C5_5 C4_5 H4_5 120.9 . . ?
C6_5 C5_5 C4_5 121.24(14) . . ?
C6_5 C5_5 H5_5 119.4 . . ?
C4_5 C5_5 H5_5 119.4 . . ?
C5_5 C6_5 C7_5 120.07(15) . . ?
C5_5 C6_5 H6_5 120.0 . . ?
C7_5 C6_5 H6_5 120.0 . . ?
C2_5 C7_5 C6_5 119.51(14) . . ?
C2_5 C7_5 H7_5 120.2 . . ?
C6_5 C7_5 H7_5 120.2 . . ?
O11_5 B8_5 O15_5 113.33(13) . . ?
O11_5 B8_5 O16_5 108.38(11) . . ?
O15_5 B8_5 O16_5 108.10(11) . . ?
O11_5 B8_5 C1_5 113.99(11) . . ?
O15_5 B8_5 C1_5 109.83(12) . . ?
O16_5 B8_5 C1_5 102.47(12) . . ?
O11_5 B9_5 O12_5 123.39(13) . . ?
O11_5 B9_5 O13_5 121.48(13) . . ?
O12_5 B9_5 O13_5 115.12(14) . . ?
O15_5 B10_5 O14_5 121.85(13) . . ?
O15_5 B10_5 O13_5 121.48(13) . . ?
O14_5 B10_5 O13_5 116.66(14) . . ?
B9_5 O11_5 B8_5 122.19(11) . . ?
B9_5 O12_5 H12_5 109.5 . . ?
B9_5 O13_5 B10_5 118.83(12) . . ?
B10_5 O14_5 H14_5 109.5 . . ?
B10_5 O15_5 B8_5 122.33(11) . . ?
C3_5 O16_5 B8_5 107.69(11) . . ?
C7_4 N17_5 C7_3 109.15(11) . . ?
C7_4 N17_5 C1_5 115.73(11) . . ?
C7_3 N17_5 C1_5 110.72(10) . . ?
C7_4 N17_5 H17_5 106.9 . . ?
C7_3 N17_5 H17_5 106.9 . . ?
C1_5 N17_5 H17_5 106.9 . . ?

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
C6_3 C1_3 C2_3 C3_3 -0.8(2) . . . . ?
C7_3 C1_3 C2_3 C3_3 173.98(12) . . . . ?
C1_3 C2_3 C3_3 C4_3 -0.1(2) . . . . ?
C2_3 C3_3 C4_3 C5_3 0.8(2) . . . . ?
C3_3 C4_3 C5_3 C6_3 -0.7(2) . . . . ?
C4_3 C5_3 C6_3 C1_3 -0.1(2) . . . . ?
C2_3 C1_3 C6_3 C5_3 0.9(2) . . . . ?
C7_3 C1_3 C6_3 C5_3 -173.96(13) . . . . ?
C2_3 C1_3 C7_3 N17_5 100.64(15) . . . . ?
C6_3 C1_3 C7_3 N17_5 -84.60(16) . . . . ?
C6_4 C1_4 C2_4 C3_4 0.5(2) . . . . ?
C7_4 C1_4 C2_4 C3_4 179.38(14) . . . . ?
C1_4 C2_4 C3_4 C4_4 -0.7(2) . . . . ?
C2_4 C3_4 C4_4 C5_4 0.4(2) . . . . ?
C3_4 C4_4 C5_4 C6_4 0.1(2) . . . . ?
C2_4 C1_4 C6_4 C5_4 -0.1(2) . . . . ?
C7_4 C1_4 C6_4 C5_4 -178.85(14) . . . . ?
C4_4 C5_4 C6_4 C1_4 -0.2(2) . . . . ?
C6_4 C1_4 C7_4 N17_5 -58.57(18) . . . . ?
C2_4 C1_4 C7_4 N17_5 122.65(14) . . . . ?
N17_5 C1_5 C2_5 C7_5 74.12(18) . . . . ?
B8_5 C1_5 C2_5 C7_5 -165.21(14) . . . . ?
N17_5 C1_5 C2_5 C3_5 -111.26(13) . . . . ?
B8_5 C1_5 C2_5 C3_5 9.42(13) . . . . ?
C7_5 C2_5 C3_5 O16_5 178.59(11) . . . . ?
C1_5 C2_5 C3_5 O16_5 3.26(15) . . . . ?
C7_5 C2_5 C3_5 C4_5 -0.85(19) . . . . ?
C1_5 C2_5 C3_5 C4_5 -176.18(12) . . . . ?
O16_5 C3_5 C4_5 C5_5 -178.40(12) . . . . ?
C2_5 C3_5 C4_5 C5_5 1.0(2) . . . . ?
C3_5 C4_5 C5_5 C6_5 -0.5(2) . . . . ?
C4_5 C5_5 C6_5 C7_5 -0.1(2) . . . . ?
C3_5 C2_5 C7_5 C6_5 0.2(2) . . . . ?
C1_5 C2_5 C7_5 C6_5 174.37(13) . . . . ?
C5_5 C6_5 C7_5 C2_5 0.2(2) . . . . ?
C2_5 C1_5 B8_5 O11_5 -134.08(12) . . . . ?
N17_5 C1_5 B8_5 O11_5 -11.93(16) . . . . ?
C2_5 C1_5 B8_5 O15_5 97.50(13) . . . . ?
N17_5 C1_5 B8_5 O15_5 -140.34(11) . . . . ?
C2_5 C1_5 B8_5 O16_5 -17.21(12) . . . . ?
N17_5 C1_5 B8_5 O16_5 104.95(12) . . . . ?
O12_5 B9_5 O11_5 B8_5 -176.79(13) . . . . ?
O13_5 B9_5 O11_5 B8_5 1.9(2) . . . . ?
O15_5 B8_5 O11_5 B9_5 0.67(19) . . . . ?
O16_5 B8_5 O11_5 B9_5 120.67(13) . . . . ?
C1_5 B8_5 O11_5 B9_5 -125.94(14) . . . . ?
O11_5 B9_5 O13_5 B10_5 -5.9(2) . . . . ?
O12_5 B9_5 O13_5 B10_5 172.87(12) . . . . ?
O15_5 B10_5 O13_5 B9_5 7.5(2) . . . . ?
O14_5 B10_5 O13_5 B9_5 -173.45(13) . . . . ?
O14_5 B10_5 O15_5 B8_5 175.95(13) . . . . ?
O13_5 B10_5 O15_5 B8_5 -5.0(2) . . . . ?
O11_5 B8_5 O15_5 B10_5 0.89(19) . . . . ?
O16_5 B8_5 O15_5 B10_5 -119.26(14) . . . . ?
C1_5 B8_5 O15_5 B10_5 129.67(14) . . . . ?
C4_5 C3_5 O16_5 B8_5 163.70(12) . . . . ?
C2_5 C3_5 O16_5 B8_5 -15.73(14) . . . . ?
O11_5 B8_5 O16_5 C3_5 140.74(11) . . . . ?
O15_5 B8_5 O16_5 C3_5 -96.05(13) . . . . ?
C1_5 B8_5 O16_5 C3_5 19.92(12) . . . . ?
C1_4 C7_4 N17_5 C7_3 -172.88(11) . . . . ?
C1_4 C7_4 N17_5 C1_5 -47.21(16) . . . . ?
C1_3 C7_3 N17_5 C7_4 -77.08(14) . . . . ?
C1_3 C7_3 N17_5 C1_5 154.41(12) . . . . ?
C2_5 C1_5 N17_5 C7_4 -79.78(15) . . . . ?
B8_5 C1_5 N17_5 C7_4 165.61(11) . . . . ?
C2_5 C1_5 N17_5 C7_3 45.08(15) . . . . ?
B8_5 C1_5 N17_5 C7_3 -69.53(14) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/toluene'
####################################################################### 
# 
# 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_cmpd_4p
_database_code_depnum_ccdc_archive 'CCDC 1964348'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_audit_creation_date             2019-11-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yudha_prawira.budiman@uni_wuerzburg.de
wenbo.ming@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_common            ?
_chemical_name_systematic        
5,7-di-tert-butyl-4',6'-dihydroxy-3-(morpholino-4-ium)-3H-spiro[benzo[d][1,2]oxaborole-2,2'-[1,3,5,2,4,6]trioxatriborinan]-2-uide
_chemical_formula_moiety         'C19 H32 B3 N O7'
_chemical_formula_sum            'C19 H32 B3 N O7'
_chemical_formula_weight         418.88
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.314(7)
_cell_length_b                   11.980(8)
_cell_length_c                   17.961(10)
_cell_angle_alpha                72.586(9)
_cell_angle_beta                 79.494(13)
_cell_angle_gamma                72.755(19)
_cell_volume                     2207(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.59
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0749 before and 0.0626 after correction. The Ratio of 
minimum to maximum transmission is 0.8078. The λ/2 correction factor 
is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.204
_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold
nitrogen (Bruker Kryoflex2).
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1277
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         1.895
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.6 mm double-pinhole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_size              '0.1 x 1 mm fine focus'
_diffrn_source_type              'Nonius FR-591'
_diffrn_source_voltage           50
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4916
_reflns_number_total             9038
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         9038
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+2.3934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1569
_refine_special_details          
;
 'The distances between atoms H5O_1 and H5O_$2 were kept during refinement 
 at the value of 2.2 using DFIX restraint.'
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H5O_1-H5O_$1
 2.2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), N1(H1N), C1(H1), N1(H1N)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C16(H16A,H16B), C19(H19A,
 H19B), C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C5(H5), C7(H7)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C9(H9A,H9B,
 H9C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C14(H14A,
 H14B,H14C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C),
 C9(H9A,H9B,H9C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5O), O4(H4), O5(H5O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.5270(2) 0.1178(2) 0.25725(13) 0.0232(6) Uani 1 1 d . . . . .
C2 C 0.3477(3) 0.2758(3) 0.24817(19) 0.0196(8) Uani 1 1 d . . . . .
C3 C 0.4461(3) 0.2052(3) 0.2092(2) 0.0205(8) Uani 1 1 d . . . . .
C4 C 0.4594(3) 0.2252(3) 0.12778(19) 0.0185(8) Uani 1 1 d . . . . .
C5 C 0.3719(3) 0.3238(3) 0.08819(19) 0.0190(8) Uani 1 1 d . . . . .
H5 H 0.378447 0.340867 0.032651 0.023 Uiso 1 1 calc R . . . .
C6 C 0.2753(3) 0.3994(3) 0.12470(19) 0.0188(8) Uani 1 1 d . . . . .
O6 O 0.5902(2) 0.2132(2) 0.34099(13) 0.0242(6) Uani 1 1 d . . . . .
C7 C 0.2641(3) 0.3730(3) 0.2061(2) 0.0205(8) Uani 1 1 d . . . . .
H7 H 0.198833 0.422031 0.232759 0.025 Uiso 1 1 calc R . . . .
O7 O 0.0291(2) 0.1017(2) 0.41096(14) 0.0278(6) Uani 1 1 d . . . . .
C1 C 0.3606(3) 0.2336(3) 0.33528(19) 0.0210(8) Uani 1 1 d . . . . .
H1 H 0.357374 0.304125 0.355136 0.025 Uiso 1 1 calc R . . . .
C13 C 0.2146(3) 0.5294(4) -0.0096(2) 0.0306(9) Uani 1 1 d . . . . .
H13A H 0.156076 0.602583 -0.036606 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.208816 0.459565 -0.025105 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.299443 0.539150 -0.023885 0.046 Uiso 1 1 calc GR . . . .
C12 C 0.1822(3) 0.5089(3) 0.07939(19) 0.0222(8) Uani 1 1 d . . . . .
C11 C 0.5562(3) 0.1792(4) -0.0027(2) 0.0325(10) Uani 1 1 d . . . . .
H11A H 0.559039 0.263729 -0.025628 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.477546 0.169196 -0.011755 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.625867 0.126420 -0.027220 0.049 Uiso 1 1 calc GR . . . .
C10 C 0.6899(3) 0.1605(4) 0.0985(2) 0.0338(10) Uani 1 1 d . . . . .
H10A H 0.758467 0.111514 0.070718 0.051 Uiso 1 1 calc GR . . . .
H10B H 0.699758 0.133865 0.154736 0.051 Uiso 1 1 calc GR . . . .
H10C H 0.690805 0.245922 0.078387 0.051 Uiso 1 1 calc GR . . . .
C9 C 0.5664(4) 0.0111(3) 0.1189(2) 0.0317(9) Uani 1 1 d . . . . .
H9A H 0.488647 -0.000826 0.109842 0.047 Uiso 1 1 calc GR . . . .
H9B H 0.573883 -0.013093 0.175324 0.047 Uiso 1 1 calc GR . . . .
H9C H 0.636991 -0.038309 0.092630 0.047 Uiso 1 1 calc GR . . . .
C8 C 0.5657(3) 0.1454(3) 0.08562(19) 0.0223(8) Uani 1 1 d . . . . .
C15 C 0.1829(3) 0.6250(3) 0.1001(2) 0.0271(9) Uani 1 1 d . . . . .
H15A H 0.265832 0.639518 0.084897 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.161646 0.614992 0.156640 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.121620 0.694016 0.071723 0.041 Uiso 1 1 calc GR . . . .
C14 C 0.0508(3) 0.4894(3) 0.1005(2) 0.0282(9) Uani 1 1 d . . . . .
H14A H -0.009053 0.561897 0.074096 0.042 Uiso 1 1 calc GR . . . .
H14B H 0.029491 0.473960 0.157404 0.042 Uiso 1 1 calc GR . . . .
H14C H 0.048168 0.419764 0.083488 0.042 Uiso 1 1 calc GR . . . .
B1 B 0.5015(4) 0.1446(4) 0.3361(2) 0.0219(9) Uani 1 1 d . . . . .
B2 B 0.7039(4) 0.1504(4) 0.3638(2) 0.0215(9) Uani 1 1 d . . . . .
O2 O 0.7292(2) 0.0289(2) 0.40281(14) 0.0259(6) Uani 1 1 d . . . . .
B3 B 0.6307(4) -0.0248(4) 0.4228(2) 0.0207(9) Uani 1 1 d . . . . .
O3 O 0.5187(2) 0.0301(2) 0.39582(13) 0.0234(6) Uani 1 1 d . . . . .
O4 O 0.7936(2) 0.2111(2) 0.35421(14) 0.0254(6) Uani 1 1 d . . . . .
H4 H 0.859298 0.161920 0.370918 0.038 Uiso 1 1 calc GR . . . .
O5 O 0.6560(2) -0.1372(2) 0.47229(13) 0.0237(6) Uani 1 1 d . . . . .
H5O H 0.591767 -0.162905 0.483486 0.036 Uiso 1 1 calc DGR . . . .
N1 N 0.2616(2) 0.1696(3) 0.38326(15) 0.0195(7) Uani 1 1 d . . . . .
H1N H 0.290444 0.128860 0.436525 0.023 Uiso 1 1 calc R . . . .
C17 C 0.1458(3) 0.0135(3) 0.4038(2) 0.0286(9) Uani 1 1 d . . . . .
H17A H 0.134410 -0.047501 0.380676 0.034 Uiso 1 1 calc R . . . .
H17B H 0.173457 -0.028854 0.456603 0.034 Uiso 1 1 calc R . . . .
C18 C 0.0454(3) 0.1876(3) 0.4469(2) 0.0245(8) Uani 1 1 d . . . . .
H18A H 0.076153 0.144858 0.498831 0.029 Uiso 1 1 calc R . . . .
H18B H -0.035526 0.245968 0.454854 0.029 Uiso 1 1 calc R . . . .
C19 C 0.1376(3) 0.2547(3) 0.39519(19) 0.0226(8) Uani 1 1 d . . . . .
H19A H 0.105683 0.298629 0.343706 0.027 Uiso 1 1 calc R . . . .
H19B H 0.146637 0.315098 0.419769 0.027 Uiso 1 1 calc R . . . .
C16 C 0.2451(3) 0.0723(3) 0.3527(2) 0.0245(8) Uani 1 1 d . . . . .
H16A H 0.325080 0.009940 0.351037 0.029 Uiso 1 1 calc R . . . .
H16B H 0.221372 0.107626 0.298497 0.029 Uiso 1 1 calc R . . . .
C1_1 C 0.3627(3) 0.6870(3) 0.34486(19) 0.0204(8) Uani 1 1 d . . . . .
H1_1 H 0.393425 0.737308 0.368678 0.025 Uiso 1 1 calc R . . . .
O1_1 O 0.1845(2) 0.5969(2) 0.38488(13) 0.0207(5) Uani 1 1 d . . . . .
C2_1 C 0.2503(3) 0.7623(3) 0.30215(19) 0.0198(8) Uani 1 1 d . . . . .
C3_1 C 0.1545(3) 0.7044(3) 0.32987(19) 0.0190(8) Uani 1 1 d . . . . .
C4_1 C 0.0367(3) 0.7550(3) 0.30188(19) 0.0206(8) Uani 1 1 d . . . . .
C5_1 C 0.0238(3) 0.8646(3) 0.24475(18) 0.0196(8) Uani 1 1 d . . . . .
H5_1 H -0.054637 0.900996 0.224572 0.023 Uiso 1 1 calc R . . . .
C6_1 C 0.1177(3) 0.9255(3) 0.21456(19) 0.0206(8) Uani 1 1 d . . . . .
O6_1 O 0.2774(2) 0.6128(2) 0.49089(13) 0.0232(6) Uani 1 1 d . . . . .
C7_1 C 0.2317(3) 0.8730(3) 0.24493(19) 0.0205(8) Uani 1 1 d . . . . .
H7_1 H 0.297192 0.912203 0.226833 0.025 Uiso 1 1 calc R . . . .
O7_1 O 0.5991(2) 0.5845(2) 0.14567(14) 0.0330(7) Uani 1 1 d . . . . .
N1_1 N 0.4674(2) 0.6253(3) 0.29184(15) 0.0189(6) Uani 1 1 d . . . . .
H1N_1 H 0.526543 0.560521 0.326935 0.023 Uiso 1 1 calc R . . . .
C19_1 C 0.5402(3) 0.7089(3) 0.2379(2) 0.0255(9) Uani 1 1 d . . . . .
H19A_1 H 0.575177 0.745079 0.268816 0.031 Uiso 1 1 calc R . . . .
H19B_1 H 0.484728 0.775227 0.202329 0.031 Uiso 1 1 calc R . . . .
C18_1 C 0.6448(3) 0.6395(4) 0.1900(2) 0.0326(10) Uani 1 1 d . . . . .
H18A_1 H 0.692034 0.695575 0.154172 0.039 Uiso 1 1 calc R . . . .
H18B_1 H 0.702572 0.576281 0.225742 0.039 Uiso 1 1 calc R . . . .
C17_1 C 0.5334(3) 0.5003(4) 0.1969(2) 0.0292(9) Uani 1 1 d . . . . .
H17A_1 H 0.590272 0.436949 0.233070 0.035 Uiso 1 1 calc R . . . .
H17B_1 H 0.504079 0.460366 0.165483 0.035 Uiso 1 1 calc R . . . .
C16_1 C 0.4235(3) 0.5644(3) 0.2436(2) 0.0240(8) Uani 1 1 d . . . . .
H16A_1 H 0.364961 0.625655 0.207615 0.029 Uiso 1 1 calc R . . . .
H16B_1 H 0.379072 0.505238 0.278689 0.029 Uiso 1 1 calc R . . . .
C15_1 C -0.1897(3) 0.7665(4) 0.2976(2) 0.0298(9) Uani 1 1 d . . . . .
H15A_1 H -0.212231 0.846484 0.307783 0.045 Uiso 1 1 calc GR . . . .
H15B_1 H -0.255907 0.725652 0.322051 0.045 Uiso 1 1 calc GR . . . .
H15C_1 H -0.179151 0.775633 0.240911 0.045 Uiso 1 1 calc GR . . . .
C14_1 C -0.0284(3) 0.5705(3) 0.3098(2) 0.0306(9) Uani 1 1 d . . . . .
H14A_1 H -0.092044 0.525823 0.332411 0.046 Uiso 1 1 calc GR . . . .
H14B_1 H 0.051061 0.522329 0.330083 0.046 Uiso 1 1 calc GR . . . .
H14C_1 H -0.019176 0.586178 0.252559 0.046 Uiso 1 1 calc GR . . . .
C13_1 C -0.0926(3) 0.6659(4) 0.4220(2) 0.0292(9) Uani 1 1 d . . . . .
H13A_1 H -0.015116 0.620178 0.445636 0.044 Uiso 1 1 calc GR . . . .
H13B_1 H -0.154648 0.618810 0.441175 0.044 Uiso 1 1 calc GR . . . .
H13C_1 H -0.123892 0.742972 0.436440 0.044 Uiso 1 1 calc GR . . . .
C12_1 C -0.0677(3) 0.6907(3) 0.3322(2) 0.0216(8) Uani 1 1 d . . . . .
C11_1 C 0.2029(3) 1.0975(4) 0.1218(2) 0.0305(9) Uani 1 1 d . . . . .
H11A_1 H 0.228333 1.116477 0.164988 0.046 Uiso 1 1 calc GR . . . .
H11B_1 H 0.181442 1.171540 0.079434 0.046 Uiso 1 1 calc GR . . . .
H11C_1 H 0.271567 1.037932 0.102126 0.046 Uiso 1 1 calc GR . . . .
C10_1 C -0.0143(3) 1.1398(3) 0.1842(2) 0.0307(9) Uani 1 1 d . . . . .
H10A_1 H 0.013838 1.155424 0.227656 0.046 Uiso 1 1 calc GR . . . .
H10B_1 H -0.088379 1.108786 0.203088 0.046 Uiso 1 1 calc GR . . . .
H10C_1 H -0.034681 1.215164 0.142697 0.046 Uiso 1 1 calc GR . . . .
C9_1 C 0.0488(3) 1.0253(4) 0.0803(2) 0.0309(9) Uani 1 1 d . . . . .
H9A_1 H -0.024813 0.993321 0.096903 0.046 Uiso 1 1 calc GR . . . .
H9B_1 H 0.116524 0.967346 0.058487 0.046 Uiso 1 1 calc GR . . . .
H9C_1 H 0.028759 1.102445 0.040216 0.046 Uiso 1 1 calc GR . . . .
C8_1 C 0.0897(3) 1.0455(3) 0.1514(2) 0.0241(8) Uani 1 1 d . . . . .
B1_1 B 0.3040(4) 0.5855(4) 0.4139(2) 0.0199(9) Uani 1 1 d . . . . .
B2_1 B 0.3240(4) 0.5340(4) 0.5557(2) 0.0217(9) Uani 1 1 d . . . . .
O2_1 O 0.3991(2) 0.4181(2) 0.55514(13) 0.0213(5) Uani 1 1 d . . . . .
B3_1 B 0.4268(3) 0.3887(4) 0.4847(2) 0.0210(9) Uani 1 1 d . . . . .
O3_1 O 0.3827(2) 0.4625(2) 0.41847(13) 0.0208(5) Uani 1 1 d . . . . .
O4_1 O 0.3086(2) 0.5561(2) 0.62744(13) 0.0223(6) Uani 1 1 d . . . . .
H4_1 H 0.265994 0.627521 0.624786 0.033 Uiso 1 1 calc GR . . . .
O5_1 O 0.5053(2) 0.2748(2) 0.48484(14) 0.0259(6) Uani 1 1 d . . . . .
H5O_1 H 0.527329 0.269849 0.438432 0.039 Uiso 1 1 calc DGR . . . .


_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 C3 1.363(4) . ?
O1 B1 1.503(4) . ?
C2 C3 1.399(5) . ?
C2 C7 1.380(5) . ?
C2 C1 1.514(5) . ?
C3 C4 1.395(5) . ?
C4 C5 1.394(5) . ?
C4 C8 1.534(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(5) . ?
C6 C7 1.390(5) . ?
C6 C12 1.532(5) . ?
O6 B1 1.502(5) . ?
O6 B2 1.350(5) . ?
C7 H7 0.9500 . ?
O7 C17 1.438(4) . ?
O7 C18 1.437(4) . ?
C1 H1 1.0000 . ?
C1 B1 1.634(5) . ?
C1 N1 1.532(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C12 1.534(5) . ?
C12 C15 1.545(5) . ?
C12 C14 1.535(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C8 1.531(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C8 1.535(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C8 1.537(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
B1 O3 1.452(5) . ?
B2 O2 1.381(5) . ?
B2 O4 1.374(5) . ?
O2 B3 1.388(5) . ?
B3 O3 1.346(5) . ?
B3 O5 1.354(5) . ?
O4 H4 0.8400 . ?
O5 H5O 0.8400 . ?
N1 H1N 1.0000 . ?
N1 C19 1.492(4) . ?
N1 C16 1.498(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.520(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.515(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C1_1 H1_1 1.0000 . ?
C1_1 C2_1 1.510(5) . ?
C1_1 N1_1 1.532(4) . ?
C1_1 B1_1 1.653(5) . ?
O1_1 C3_1 1.361(4) . ?
O1_1 B1_1 1.491(4) . ?
C2_1 C3_1 1.394(5) . ?
C2_1 C7_1 1.399(5) . ?
C3_1 C4_1 1.407(5) . ?
C4_1 C5_1 1.390(5) . ?
C4_1 C12_1 1.529(5) . ?
C5_1 H5_1 0.9500 . ?
C5_1 C6_1 1.403(5) . ?
C6_1 C7_1 1.388(5) . ?
C6_1 C8_1 1.530(5) . ?
O6_1 B1_1 1.473(4) . ?
O6_1 B2_1 1.340(5) . ?
C7_1 H7_1 0.9500 . ?
O7_1 C18_1 1.415(4) . ?
O7_1 C17_1 1.434(4) . ?
N1_1 H1N_1 1.0000 . ?
N1_1 C19_1 1.495(4) . ?
N1_1 C16_1 1.509(4) . ?
C19_1 H19A_1 0.9900 . ?
C19_1 H19B_1 0.9900 . ?
C19_1 C18_1 1.518(5) . ?
C18_1 H18A_1 0.9900 . ?
C18_1 H18B_1 0.9900 . ?
C17_1 H17A_1 0.9900 . ?
C17_1 H17B_1 0.9900 . ?
C17_1 C16_1 1.510(5) . ?
C16_1 H16A_1 0.9900 . ?
C16_1 H16B_1 0.9900 . ?
C15_1 H15A_1 0.9800 . ?
C15_1 H15B_1 0.9800 . ?
C15_1 H15C_1 0.9800 . ?
C15_1 C12_1 1.533(5) . ?
C14_1 H14A_1 0.9800 . ?
C14_1 H14B_1 0.9800 . ?
C14_1 H14C_1 0.9800 . ?
C14_1 C12_1 1.529(5) . ?
C13_1 H13A_1 0.9800 . ?
C13_1 H13B_1 0.9800 . ?
C13_1 H13C_1 0.9800 . ?
C13_1 C12_1 1.538(5) . ?
C11_1 H11A_1 0.9800 . ?
C11_1 H11B_1 0.9800 . ?
C11_1 H11C_1 0.9800 . ?
C11_1 C8_1 1.530(5) . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C10_1 C8_1 1.538(5) . ?
C9_1 H9A_1 0.9800 . ?
C9_1 H9B_1 0.9800 . ?
C9_1 H9C_1 0.9800 . ?
C9_1 C8_1 1.539(5) . ?
B1_1 O3_1 1.465(5) . ?
B2_1 O2_1 1.399(5) . ?
B2_1 O4_1 1.363(4) . ?
O2_1 B3_1 1.371(4) . ?
B3_1 O3_1 1.331(5) . ?
B3_1 O5_1 1.389(5) . ?
O4_1 H4_1 0.8400 . ?
O5_1 H5O_1 0.8400 . ?

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
C3 O1 B1 107.9(3) . . ?
C3 C2 C1 109.3(3) . . ?
C7 C2 C3 120.2(3) . . ?
C7 C2 C1 130.2(3) . . ?
O1 C3 C2 114.2(3) . . ?
O1 C3 C4 123.8(3) . . ?
C4 C3 C2 122.0(3) . . ?
C3 C4 C8 121.7(3) . . ?
C5 C4 C3 115.3(3) . . ?
C5 C4 C8 123.0(3) . . ?
C4 C5 H5 117.8 . . ?
C4 C5 C6 124.4(3) . . ?
C6 C5 H5 117.8 . . ?
C5 C6 C12 123.2(3) . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 C12 119.0(3) . . ?
B2 O6 B1 118.8(3) . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C18 O7 C17 109.0(3) . . ?
C2 C1 H1 109.6 . . ?
C2 C1 B1 100.8(3) . . ?
C2 C1 N1 113.4(3) . . ?
B1 C1 H1 109.6 . . ?
N1 C1 H1 109.6 . . ?
N1 C1 B1 113.4(3) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
C6 C12 C13 111.7(3) . . ?
C6 C12 C15 110.2(3) . . ?
C6 C12 C14 109.8(3) . . ?
C13 C12 C15 107.5(3) . . ?
C13 C12 C14 108.4(3) . . ?
C14 C12 C15 109.1(3) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
C4 C8 C10 108.7(3) . . ?
C4 C8 C9 110.9(3) . . ?
C11 C8 C4 112.2(3) . . ?
C11 C8 C10 108.6(3) . . ?
C11 C8 C9 108.0(3) . . ?
C10 C8 C9 108.2(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 B1 C1 103.6(3) . . ?
O6 B1 O1 109.0(3) . . ?
O6 B1 C1 109.0(3) . . ?
O3 B1 O1 108.0(3) . . ?
O3 B1 O6 110.7(3) . . ?
O3 B1 C1 116.1(3) . . ?
O6 B2 O2 121.7(3) . . ?
O6 B2 O4 119.1(3) . . ?
O4 B2 O2 118.9(3) . . ?
B2 O2 B3 117.4(3) . . ?
O3 B3 O2 123.0(3) . . ?
O3 B3 O5 122.5(3) . . ?
O5 B3 O2 114.5(3) . . ?
B3 O3 B1 119.8(3) . . ?
B2 O4 H4 109.5 . . ?
B3 O5 H5O 109.5 . . ?
C1 N1 H1N 106.4 . . ?
C19 N1 C1 113.3(3) . . ?
C19 N1 H1N 106.4 . . ?
C19 N1 C16 108.9(3) . . ?
C16 N1 C1 114.9(3) . . ?
C16 N1 H1N 106.4 . . ?
O7 C17 H17A 109.4 . . ?
O7 C17 H17B 109.4 . . ?
O7 C17 C16 111.4(3) . . ?
H17A C17 H17B 108.0 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
O7 C18 H18A 109.7 . . ?
O7 C18 H18B 109.7 . . ?
O7 C18 C19 110.0(3) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
N1 C19 C18 111.1(3) . . ?
N1 C19 H19A 109.4 . . ?
N1 C19 H19B 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N1 C16 C17 111.4(3) . . ?
N1 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C2_1 C1_1 H1_1 110.6 . . ?
C2_1 C1_1 N1_1 112.3(3) . . ?
C2_1 C1_1 B1_1 101.6(3) . . ?
N1_1 C1_1 H1_1 110.6 . . ?
N1_1 C1_1 B1_1 110.7(3) . . ?
B1_1 C1_1 H1_1 110.6 . . ?
C3_1 O1_1 B1_1 108.8(3) . . ?
C3_1 C2_1 C1_1 108.6(3) . . ?
C3_1 C2_1 C7_1 120.5(3) . . ?
C7_1 C2_1 C1_1 130.9(3) . . ?
O1_1 C3_1 C2_1 114.9(3) . . ?
O1_1 C3_1 C4_1 123.5(3) . . ?
C2_1 C3_1 C4_1 121.5(3) . . ?
C3_1 C4_1 C12_1 121.2(3) . . ?
C5_1 C4_1 C3_1 115.4(3) . . ?
C5_1 C4_1 C12_1 123.3(3) . . ?
C4_1 C5_1 H5_1 117.5 . . ?
C4_1 C5_1 C6_1 125.0(3) . . ?
C6_1 C5_1 H5_1 117.5 . . ?
C5_1 C6_1 C8_1 119.0(3) . . ?
C7_1 C6_1 C5_1 117.4(3) . . ?
C7_1 C6_1 C8_1 123.6(3) . . ?
B2_1 O6_1 B1_1 122.8(3) . . ?
C2_1 C7_1 H7_1 120.0 . . ?
C6_1 C7_1 C2_1 120.1(3) . . ?
C6_1 C7_1 H7_1 120.0 . . ?
C18_1 O7_1 C17_1 110.1(3) . . ?
C1_1 N1_1 H1N_1 107.0 . . ?
C19_1 N1_1 C1_1 113.3(3) . . ?
C19_1 N1_1 H1N_1 107.0 . . ?
C19_1 N1_1 C16_1 108.5(3) . . ?
C16_1 N1_1 C1_1 113.6(2) . . ?
C16_1 N1_1 H1N_1 107.0 . . ?
N1_1 C19_1 H19A_1 109.7 . . ?
N1_1 C19_1 H19B_1 109.7 . . ?
N1_1 C19_1 C18_1 109.8(3) . . ?
H19A_1 C19_1 H19B_1 108.2 . . ?
C18_1 C19_1 H19A_1 109.7 . . ?
C18_1 C19_1 H19B_1 109.7 . . ?
O7_1 C18_1 C19_1 111.7(3) . . ?
O7_1 C18_1 H18A_1 109.3 . . ?
O7_1 C18_1 H18B_1 109.3 . . ?
C19_1 C18_1 H18A_1 109.3 . . ?
C19_1 C18_1 H18B_1 109.3 . . ?
H18A_1 C18_1 H18B_1 108.0 . . ?
O7_1 C17_1 H17A_1 109.5 . . ?
O7_1 C17_1 H17B_1 109.5 . . ?
O7_1 C17_1 C16_1 110.5(3) . . ?
H17A_1 C17_1 H17B_1 108.1 . . ?
C16_1 C17_1 H17A_1 109.5 . . ?
C16_1 C17_1 H17B_1 109.5 . . ?
N1_1 C16_1 C17_1 109.9(3) . . ?
N1_1 C16_1 H16A_1 109.7 . . ?
N1_1 C16_1 H16B_1 109.7 . . ?
C17_1 C16_1 H16A_1 109.7 . . ?
C17_1 C16_1 H16B_1 109.7 . . ?
H16A_1 C16_1 H16B_1 108.2 . . ?
H15A_1 C15_1 H15B_1 109.5 . . ?
H15A_1 C15_1 H15C_1 109.5 . . ?
H15B_1 C15_1 H15C_1 109.5 . . ?
C12_1 C15_1 H15A_1 109.5 . . ?
C12_1 C15_1 H15B_1 109.5 . . ?
C12_1 C15_1 H15C_1 109.5 . . ?
H14A_1 C14_1 H14B_1 109.5 . . ?
H14A_1 C14_1 H14C_1 109.5 . . ?
H14B_1 C14_1 H14C_1 109.5 . . ?
C12_1 C14_1 H14A_1 109.5 . . ?
C12_1 C14_1 H14B_1 109.5 . . ?
C12_1 C14_1 H14C_1 109.5 . . ?
H13A_1 C13_1 H13B_1 109.5 . . ?
H13A_1 C13_1 H13C_1 109.5 . . ?
H13B_1 C13_1 H13C_1 109.5 . . ?
C12_1 C13_1 H13A_1 109.5 . . ?
C12_1 C13_1 H13B_1 109.5 . . ?
C12_1 C13_1 H13C_1 109.5 . . ?
C4_1 C12_1 C15_1 112.0(3) . . ?
C4_1 C12_1 C13_1 110.2(3) . . ?
C15_1 C12_1 C13_1 107.7(3) . . ?
C14_1 C12_1 C4_1 108.9(3) . . ?
C14_1 C12_1 C15_1 108.7(3) . . ?
C14_1 C12_1 C13_1 109.2(3) . . ?
H11A_1 C11_1 H11B_1 109.5 . . ?
H11A_1 C11_1 H11C_1 109.5 . . ?
H11B_1 C11_1 H11C_1 109.5 . . ?
C8_1 C11_1 H11A_1 109.5 . . ?
C8_1 C11_1 H11B_1 109.5 . . ?
C8_1 C11_1 H11C_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C8_1 C10_1 H10A_1 109.5 . . ?
C8_1 C10_1 H10B_1 109.5 . . ?
C8_1 C10_1 H10C_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
C8_1 C9_1 H9A_1 109.5 . . ?
C8_1 C9_1 H9B_1 109.5 . . ?
C8_1 C9_1 H9C_1 109.5 . . ?
C6_1 C8_1 C11_1 112.7(3) . . ?
C6_1 C8_1 C10_1 109.9(3) . . ?
C6_1 C8_1 C9_1 109.3(3) . . ?
C11_1 C8_1 C10_1 107.9(3) . . ?
C11_1 C8_1 C9_1 107.2(3) . . ?
C10_1 C8_1 C9_1 109.8(3) . . ?
O1_1 B1_1 C1_1 102.7(3) . . ?
O6_1 B1_1 C1_1 112.8(3) . . ?
O6_1 B1_1 O1_1 109.1(3) . . ?
O3_1 B1_1 C1_1 111.5(3) . . ?
O3_1 B1_1 O1_1 108.5(3) . . ?
O3_1 B1_1 O6_1 111.8(3) . . ?
O6_1 B2_1 O2_1 121.9(3) . . ?
O6_1 B2_1 O4_1 125.6(4) . . ?
O4_1 B2_1 O2_1 112.4(3) . . ?
B3_1 O2_1 B2_1 117.3(3) . . ?
O2_1 B3_1 O5_1 116.4(3) . . ?
O3_1 B3_1 O2_1 123.6(4) . . ?
O3_1 B3_1 O5_1 120.0(3) . . ?
B3_1 O3_1 B1_1 122.5(3) . . ?
B2_1 O4_1 H4_1 109.5 . . ?
B3_1 O5_1 H5O_1 109.5 . . ?

_olex2_submission_original_sample_id WM-D088-D1
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
