# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Martinez-Castro, Elisa'
'Gonzalez-Benjumea, Alejandro'
'Lopez, Oscar'
'Maya, Ines'
'Alvarez, Eleuterio'
'Fernandez-Bolanos, Jose'

_publ_contact_author_name        'Fernandez-Bolanos, Jose'
_publ_contact_author_email       bolanos@us.es

_publ_section_title              
;
Intramolecular cyclization of alkoxyaminosugars:
access to novel glycosidase inhibitor families
;

# Attachment '- ea11610a.cif'

data_ea11610a
_database_code_depnum_ccdc_archive 'CCDC 864830'
#TrackingRef '- ea11610a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H29 B N2 O6'
_chemical_formula_sum            'C20 H29 B N2 O6'
_chemical_formula_weight         404.26
_chemical_absolute_configuration rm

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.5632(3)
_cell_length_b                   11.8122(4)
_cell_length_c                   10.9084(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6900(10)
_cell_angle_gamma                90.00
_cell_volume                     1102.91(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8206
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      30.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.45
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15535
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         30.51
_reflns_number_total             3469
_reflns_number_gt                3271
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0542P)^2^+0.1073P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3469
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31023(10) 0.32805(8) 0.11730(9) 0.02255(19) Uani 1 1 d . . .
O2 O 0.39902(12) 0.29180(11) 0.31679(10) 0.0324(2) Uani 1 1 d . . .
O3 O 0.63733(12) 0.35282(11) 0.26116(9) 0.0310(2) Uani 1 1 d . . .
O4 O 0.57041(12) 0.25398(10) -0.04820(9) 0.0291(2) Uani 1 1 d . . .
O5 O 0.46067(13) 0.41964(11) -0.11075(9) 0.0321(2) Uani 1 1 d . . .
O6 O 0.11131(11) 0.52390(9) 0.22853(9) 0.02296(19) Uani 1 1 d . . .
N1 N 0.08512(12) 0.49101(9) 0.10146(10) 0.0192(2) Uani 1 1 d . . .
H1N H 0.0624 0.4140 0.1006 0.023 Uiso 1 1 calc R . .
N2 N 0.01299(17) 0.77091(14) -0.0187(2) 0.0524(5) Uani 1 1 d . . .
C1 C 0.41039(15) 0.26140(12) 0.19178(13) 0.0247(3) Uani 1 1 d . . .
H1 H 0.3825 0.1797 0.1811 0.030 Uiso 1 1 calc R . .
C2 C 0.58475(15) 0.27839(13) 0.16601(13) 0.0261(3) Uani 1 1 d . . .
H2 H 0.6417 0.2046 0.1720 0.031 Uiso 1 1 calc R . .
C3 C 0.61384(15) 0.33450(13) 0.04462(12) 0.0240(3) Uani 1 1 d . . .
H3 H 0.7264 0.3556 0.0387 0.029 Uiso 1 1 calc R . .
C4 C 0.50826(15) 0.43703(13) 0.01479(12) 0.0222(2) Uani 1 1 d . . .
H4 H 0.5692 0.5089 0.0235 0.027 Uiso 1 1 calc R . .
C5 C 0.36718(13) 0.43989(11) 0.09679(11) 0.0192(2) Uani 1 1 d . . .
H5 H 0.3978 0.4753 0.1772 0.023 Uiso 1 1 calc R . .
C6 C 0.23352(14) 0.50647(11) 0.03756(12) 0.0211(2) Uani 1 1 d . . .
H6A H 0.2610 0.5879 0.0376 0.025 Uiso 1 1 calc R . .
H6B H 0.2190 0.4821 -0.0489 0.025 Uiso 1 1 calc R . .
C7 C 0.54841(18) 0.32712(16) 0.36579(13) 0.0318(3) Uani 1 1 d . . .
C8 C 0.5290(3) 0.4338(2) 0.43898(17) 0.0484(5) Uani 1 1 d . . .
H8A H 0.6319 0.4620 0.4663 0.073 Uiso 1 1 calc R . .
H8B H 0.4661 0.4178 0.5106 0.073 Uiso 1 1 calc R . .
H8C H 0.4763 0.4912 0.3878 0.073 Uiso 1 1 calc R . .
C9 C 0.6231(3) 0.2307(2) 0.43946(18) 0.0496(5) Uani 1 1 d . . .
H9A H 0.6361 0.1648 0.3861 0.074 Uiso 1 1 calc R . .
H9B H 0.5557 0.2104 0.5071 0.074 Uiso 1 1 calc R . .
H9C H 0.7254 0.2548 0.4726 0.074 Uiso 1 1 calc R . .
C10 C 0.52905(16) 0.31709(14) -0.15503(13) 0.0278(3) Uani 1 1 d . . .
C11 C 0.4051(2) 0.2517(2) -0.22669(17) 0.0436(4) Uani 1 1 d . . .
H11A H 0.4476 0.1786 -0.2517 0.065 Uiso 1 1 calc R . .
H11B H 0.3724 0.2950 -0.2997 0.065 Uiso 1 1 calc R . .
H11C H 0.3148 0.2393 -0.1751 0.065 Uiso 1 1 calc R . .
C12 C 0.67292(18) 0.3446(2) -0.22756(14) 0.0379(4) Uani 1 1 d . . .
H12A H 0.7494 0.3843 -0.1746 0.057 Uiso 1 1 calc R . .
H12B H 0.6432 0.3929 -0.2975 0.057 Uiso 1 1 calc R . .
H12C H 0.7191 0.2742 -0.2574 0.057 Uiso 1 1 calc R . .
C13 C -0.01514(16) 0.68106(13) 0.01193(18) 0.0327(3) Uani 1 1 d . . .
C14 C 0.03264(19) 0.44397(13) 0.30608(14) 0.0301(3) Uani 1 1 d . . .
H14A H 0.0931 0.3726 0.3121 0.036 Uiso 1 1 calc R . .
H14B H -0.0724 0.4265 0.2708 0.036 Uiso 1 1 calc R . .
C15 C 0.01882(17) 0.49568(14) 0.43057(14) 0.0296(3) Uani 1 1 d . . .
C16 C -0.0762(3) 0.5882(2) 0.4478(2) 0.0506(5) Uani 1 1 d . . .
H16 H -0.1276 0.6228 0.3792 0.061 Uiso 1 1 calc R . .
C17 C -0.0974(4) 0.6312(2) 0.5644(3) 0.0681(7) Uani 1 1 d . . .
H17 H -0.1646 0.6942 0.5753 0.082 Uiso 1 1 calc R . .
C18 C -0.0228(4) 0.5838(3) 0.6629(2) 0.0734(9) Uani 1 1 d . . .
H18 H -0.0353 0.6149 0.7424 0.088 Uiso 1 1 calc R . .
C19 C 0.0696(5) 0.4920(3) 0.6481(2) 0.0910(12) Uani 1 1 d . . .
H19 H 0.1189 0.4573 0.7176 0.109 Uiso 1 1 calc R . .
C20 C 0.0929(4) 0.4485(2) 0.5317(2) 0.0629(7) Uani 1 1 d . . .
H20 H 0.1605 0.3856 0.5219 0.075 Uiso 1 1 calc R . .
B1 B -0.06145(17) 0.55496(13) 0.04196(17) 0.0257(3) Uani 1 1 d . . .
H1A H -0.0966 0.5158 -0.0342 0.031 Uiso 1 1 calc R . .
H1B H -0.1486 0.5543 0.0996 0.031 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0189(4) 0.0199(4) 0.0288(5) 0.0045(4) -0.0005(3) -0.0013(3)
O2 0.0287(5) 0.0440(6) 0.0247(5) 0.0091(5) 0.0062(4) -0.0012(4)
O3 0.0252(5) 0.0484(7) 0.0195(5) 0.0015(5) 0.0003(3) -0.0046(5)
O4 0.0331(5) 0.0314(5) 0.0230(5) -0.0029(4) 0.0008(4) 0.0067(4)
O5 0.0378(5) 0.0397(6) 0.0189(4) 0.0031(4) 0.0018(4) 0.0135(5)
O6 0.0257(4) 0.0222(4) 0.0211(4) -0.0024(4) 0.0034(3) -0.0031(3)
N1 0.0204(4) 0.0164(5) 0.0207(5) -0.0013(4) 0.0004(3) -0.0002(4)
N2 0.0265(6) 0.0266(7) 0.1033(15) 0.0196(9) -0.0128(7) 0.0012(5)
C1 0.0247(6) 0.0220(6) 0.0273(7) 0.0064(5) 0.0015(5) 0.0011(5)
C2 0.0241(6) 0.0309(7) 0.0234(6) 0.0032(5) 0.0002(5) 0.0069(5)
C3 0.0200(5) 0.0306(7) 0.0214(6) -0.0001(5) 0.0022(4) 0.0042(5)
C4 0.0207(5) 0.0254(6) 0.0207(6) 0.0024(5) 0.0025(4) 0.0004(5)
C5 0.0187(5) 0.0181(5) 0.0209(5) 0.0009(5) 0.0010(4) 0.0003(4)
C6 0.0198(5) 0.0219(6) 0.0217(6) 0.0034(5) 0.0018(4) 0.0026(4)
C7 0.0323(7) 0.0430(8) 0.0203(6) 0.0071(6) 0.0018(5) 0.0025(6)
C8 0.0666(12) 0.0511(11) 0.0277(8) -0.0040(8) 0.0063(7) -0.0039(10)
C9 0.0544(10) 0.0658(13) 0.0286(8) 0.0160(9) 0.0011(7) 0.0206(10)
C10 0.0259(6) 0.0376(8) 0.0199(6) -0.0025(6) 0.0016(4) 0.0034(5)
C11 0.0400(8) 0.0567(12) 0.0338(9) -0.0052(8) -0.0056(7) -0.0098(8)
C12 0.0292(7) 0.0620(12) 0.0230(7) -0.0025(7) 0.0062(5) 0.0025(7)
C13 0.0200(6) 0.0221(6) 0.0557(10) 0.0061(7) -0.0063(6) 0.0024(5)
C14 0.0398(7) 0.0241(6) 0.0268(7) 0.0002(6) 0.0093(5) -0.0047(6)
C15 0.0314(6) 0.0303(7) 0.0276(7) -0.0013(6) 0.0096(5) -0.0003(6)
C16 0.0591(12) 0.0425(10) 0.0503(12) -0.0089(9) 0.0039(9) 0.0155(9)
C17 0.0818(17) 0.0525(13) 0.0717(17) -0.0252(13) 0.0307(13) 0.0072(12)
C18 0.119(2) 0.0632(15) 0.0395(12) -0.0187(12) 0.0335(14) -0.0199(16)
C19 0.160(3) 0.085(2) 0.0276(10) -0.0002(13) -0.0010(15) 0.022(2)
C20 0.0921(18) 0.0617(14) 0.0347(10) -0.0025(10) -0.0007(10) 0.0293(13)
B1 0.0206(6) 0.0191(6) 0.0370(8) 0.0031(6) -0.0043(6) -0.0005(5)

_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 1.4052(16) . ?
O1 C5 1.4282(15) . ?
O2 C1 1.4162(18) . ?
O2 C7 1.4339(19) . ?
O3 C2 1.4232(18) . ?
O3 C7 1.4233(18) . ?
O4 C10 1.4194(18) . ?
O4 C3 1.4303(17) . ?
O5 C4 1.4320(17) . ?
O5 C10 1.4353(19) . ?
O6 C14 1.4472(17) . ?
O6 N1 1.4506(14) . ?
N1 C6 1.4787(16) . ?
N1 B1 1.5872(18) . ?
N1 H1N 0.9300 . ?
N2 C13 1.141(2) . ?
C1 C2 1.5405(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.5081(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.5404(19) . ?
C3 H3 1.0000 . ?
C4 C5 1.5247(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.5173(16) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.504(3) . ?
C7 C9 1.524(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.512(2) . ?
C10 C12 1.519(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 B1 1.578(2) . ?
C14 C15 1.497(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.374(3) . ?
C15 C16 1.378(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.355(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.355(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
B1 H1A 0.9900 . ?
B1 H1B 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 C5 113.79(9) . . ?
C1 O2 C7 110.29(11) . . ?
C2 O3 C7 106.73(12) . . ?
C10 O4 C3 106.58(12) . . ?
C4 O5 C10 109.60(11) . . ?
C14 O6 N1 108.80(10) . . ?
O6 N1 C6 107.85(9) . . ?
O6 N1 B1 111.19(10) . . ?
C6 N1 B1 115.38(11) . . ?
O6 N1 H1N 107.4 . . ?
C6 N1 H1N 107.4 . . ?
B1 N1 H1N 107.4 . . ?
O1 C1 O2 110.89(12) . . ?
O1 C1 C2 113.57(11) . . ?
O2 C1 C2 103.73(11) . . ?
O1 C1 H1 109.5 . . ?
O2 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
O3 C2 C3 108.18(12) . . ?
O3 C2 C1 103.58(11) . . ?
C3 C2 C1 113.80(11) . . ?
O3 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
O4 C3 C2 106.44(12) . . ?
O4 C3 C4 103.56(10) . . ?
C2 C3 C4 114.83(11) . . ?
O4 C3 H3 110.6 . . ?
C2 C3 H3 110.6 . . ?
C4 C3 H3 110.6 . . ?
O5 C4 C5 110.86(10) . . ?
O5 C4 C3 103.76(11) . . ?
C5 C4 C3 111.33(11) . . ?
O5 C4 H4 110.2 . . ?
C5 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
O1 C5 C6 106.82(9) . . ?
O1 C5 C4 110.58(10) . . ?
C6 C5 C4 111.25(10) . . ?
O1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
N1 C6 C5 112.53(10) . . ?
N1 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
O3 C7 O2 104.81(11) . . ?
O3 C7 C8 108.50(15) . . ?
O2 C7 C8 109.29(14) . . ?
O3 C7 C9 110.87(14) . . ?
O2 C7 C9 109.56(16) . . ?
C8 C7 C9 113.44(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O5 105.15(11) . . ?
O4 C10 C11 108.11(14) . . ?
O5 C10 C11 108.51(14) . . ?
O4 C10 C12 110.69(12) . . ?
O5 C10 C12 109.89(15) . . ?
C11 C10 C12 114.07(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 B1 174.6(2) . . ?
O6 C14 C15 108.34(12) . . ?
O6 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O6 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C20 C15 C16 118.17(18) . . ?
C20 C15 C14 121.04(16) . . ?
C16 C15 C14 120.67(16) . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.5(2) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C13 B1 N1 109.48(11) . . ?
C13 B1 H1A 109.8 . . ?
N1 B1 H1A 109.8 . . ?
C13 B1 H1B 109.8 . . ?
N1 B1 H1B 109.8 . . ?
H1A B1 H1B 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
C14 O6 N1 C6 -138.87(11) . . . . ?
C14 O6 N1 B1 93.70(13) . . . . ?
C5 O1 C1 O2 76.88(13) . . . . ?
C5 O1 C1 C2 -39.45(16) . . . . ?
C7 O2 C1 O1 -121.01(13) . . . . ?
C7 O2 C1 C2 1.25(15) . . . . ?
C7 O3 C2 C3 153.48(12) . . . . ?
C7 O3 C2 C1 32.40(14) . . . . ?
O1 C1 C2 O3 100.11(13) . . . . ?
O2 C1 C2 O3 -20.36(14) . . . . ?
O1 C1 C2 C3 -17.11(18) . . . . ?
O2 C1 C2 C3 -137.58(13) . . . . ?
C10 O4 C3 C2 154.15(10) . . . . ?
C10 O4 C3 C4 32.71(13) . . . . ?
O3 C2 C3 O4 175.81(10) . . . . ?
C1 C2 C3 O4 -69.67(14) . . . . ?
O3 C2 C3 C4 -70.24(14) . . . . ?
C1 C2 C3 C4 44.28(17) . . . . ?
C10 O5 C4 C5 -119.60(13) . . . . ?
C10 O5 C4 C3 0.01(14) . . . . ?
O4 C3 C4 O5 -19.71(13) . . . . ?
C2 C3 C4 O5 -135.34(12) . . . . ?
O4 C3 C4 C5 99.58(12) . . . . ?
C2 C3 C4 C5 -16.04(16) . . . . ?
C1 O1 C5 C6 -168.99(11) . . . . ?
C1 O1 C5 C4 69.81(13) . . . . ?
O5 C4 C5 O1 76.99(13) . . . . ?
C3 C4 C5 O1 -37.99(14) . . . . ?
O5 C4 C5 C6 -41.55(15) . . . . ?
C3 C4 C5 C6 -156.52(11) . . . . ?
O6 N1 C6 C5 56.98(13) . . . . ?
B1 N1 C6 C5 -178.04(11) . . . . ?
O1 C5 C6 N1 47.16(14) . . . . ?
C4 C5 C6 N1 167.93(11) . . . . ?
C2 O3 C7 O2 -32.04(16) . . . . ?
C2 O3 C7 C8 -148.70(13) . . . . ?
C2 O3 C7 C9 86.09(17) . . . . ?
C1 O2 C7 O3 18.42(17) . . . . ?
C1 O2 C7 C8 134.55(14) . . . . ?
C1 O2 C7 C9 -100.60(15) . . . . ?
C3 O4 C10 O5 -33.24(14) . . . . ?
C3 O4 C10 C11 -149.00(13) . . . . ?
C3 O4 C10 C12 85.39(15) . . . . ?
C4 O5 C10 O4 20.00(15) . . . . ?
C4 O5 C10 C11 135.49(14) . . . . ?
C4 O5 C10 C12 -99.16(13) . . . . ?
N1 O6 C14 C15 -163.29(11) . . . . ?
O6 C14 C15 C20 -116.3(2) . . . . ?
O6 C14 C15 C16 67.6(2) . . . . ?
C20 C15 C16 C17 -0.8(4) . . . . ?
C14 C15 C16 C17 175.5(2) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C19 -1.8(5) . . . . ?
C17 C18 C19 C20 2.3(6) . . . . ?
C16 C15 C20 C19 1.2(4) . . . . ?
C14 C15 C20 C19 -175.0(3) . . . . ?
C18 C19 C20 C15 -2.0(6) . . . . ?
N2 C13 B1 N1 132.1(17) . . . . ?
O6 N1 B1 C13 76.33(15) . . . . ?
C6 N1 B1 C13 -46.89(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.93 2.01 2.8698(18) 153.1 2_545

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035