# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_bo3424
_database_code_depnum_ccdc_archive 'CCDC 1431004'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;
_audit_creation_method           'Created with Diamond (www.crystalimpact.com)'
_audit_creation_date             15-09-30
_chemical_formula_sum            'C3 H10 N10 O'
_chemical_formula_weight         202.210
_refine_ls_R_factor_all          0.086
_cell_length_a                   3.805(3)
_cell_length_b                   7.898(6)
_cell_length_c                   15.015(11)
_cell_angle_alpha                84.83(2)
_cell_angle_beta                 82.81(2)
_cell_angle_gamma                83.49(2)
_cell_volume                     443.5(6)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-x, -y, -z'

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? 1.200
N ? 1.200
C ? 1.200
H ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.0561(4) 0.0828(2) 0.3915(1) 1.000 2 i ? d Uani 0.0361(4)
N1 N 0.4855(5) 0.3501(2) 0.1779(1) 1.000 2 i ? d Uani 0.0346(5)
N2 N 0.6476(5) 0.3907(2) 0.0954(1) 1.000 2 i ? d Uani 0.0362(5)
N3 N 0.6865(5) 0.2497(2) 0.0527(1) 1.000 2 i ? d Uani 0.0305(4)
N4 N 0.5626(4) 0.1149(2) 0.1020(1) 1.000 2 i ? d Uani 0.0307(4)
N5 N 0.2889(5) 0.0772(2) 0.2526(1) 1.000 2 i ? d Uani 0.0316(4)
N6 N 0.1894(5) 0.1672(2) 0.3201(1) 1.000 2 i ? d Uani 0.0336(4)
N7 N 0.4536(6) 0.2526(2) 0.5225(1) 1.000 2 i ? d Uani 0.0324(5)
N8 N 0.2420(5) 0.2191(2) 0.6055(1) 1.000 2 i ? d Uani 0.0300(4)
N9 N -0.1263(5) 0.3153(3) 0.7275(1) 1.000 2 i ? d Uani 0.0365(5)
N10 N 0.1508(6) 0.5074(2) 0.6234(1) 1.000 2 i ? d Uani 0.0360(5)
C1 C 0.4395(5) 0.1816(2) 0.1797(1) 1.000 2 i ? d Uani 0.0291(5)
C2 C 0.8571(6) 0.2415(3) -0.0399(1) 1.000 2 i ? d Uani 0.0367(6)
H2A H 0.9548 0.3498 -0.0604 1.000 2 i ? calc Uiso 0.04400
H2B H 0.6809 0.2212 -0.0791 1.000 2 i ? calc Uiso 0.04400
H2C H 1.0499 0.1480 -0.0424 1.000 2 i ? calc Uiso 0.04400
C3 C 0.0855(6) 0.3487(3) 0.6512(1) 1.000 2 i ? d Uani 0.0284(5)
H7A H 0.651(6) 0.190(3) 0.5230(14) 1.000 2 i ? d Uiso 0.046(8)
H7B H 0.332(6) 0.223(3) 0.4808(16) 1.000 2 i ? d Uiso 0.061(8)
H8 H 0.151(6) 0.120(3) 0.6202(14) 1.000 2 i ? d Uiso 0.045(7)
H9A H -0.253(6) 0.399(3) 0.7533(15) 1.000 2 i ? d Uiso 0.050(7)
H9B H -0.196(6) 0.206(4) 0.7431(16) 1.000 2 i ? d Uiso 0.071(9)
H10A H 0.300(6) 0.530(3) 0.5694(16) 1.000 2 i ? d Uiso 0.065(8)
H10B H 0.044(6) 0.587(3) 0.6549(17) 1.000 2 i ? d Uiso 0.063(8)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N6 . . 1.289(2) no
N1 N2 . . 1.341(2) no
N1 C1 . . 1.359(3) no
N2 N3 . . 1.320(2) no
N3 N4 . . 1.337(2) no
N3 C2 . . 1.463(3) no
N4 C1 . . 1.333(2) no
N5 N6 . . 1.285(2) no
N5 C1 . . 1.412(3) no
N7 N8 . . 1.417(3) no
N7 H7A . . 0.85(2) no
N7 H7B . . 0.89(2) no
N8 C3 . . 1.326(2) no
N8 H8 . . 0.89(2) no
N9 C3 . . 1.340(3) no
N9 H9A . . 0.86(2) no
N9 H9B . . 0.93(3) no
N10 C3 . . 1.325(3) no
N10 H10A . . 0.94(2) no
N10 H10B . . 0.86(3) no
C2 H2A . . 0.9800 no
C2 H2B . . 0.9800 no
C2 H2C . . 0.9800 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . . 105.59(16) no
N3 N2 N1 . . . 106.05(16) no
N2 N3 N4 . . . 114.11(17) no
N2 N3 C2 . . . 122.72(17) no
N4 N3 C2 . . . 123.16(17) no
C1 N4 N3 . . . 101.76(17) no
N6 N5 C1 . . . 109.34(17) no
N5 N6 O1 . . . 114.45(17) no
N8 N7 H7A . . . 108.4(15) no
N8 N7 H7B . . . 105.3(15) no
H7A N7 H7B . . . 110.(2) no
C3 N8 N7 . . . 119.48(18) no
C3 N8 H8 . . . 115.2(14) no
N7 N8 H8 . . . 122.4(14) no
C3 N9 H9A . . . 119.1(15) no
C3 N9 H9B . . . 120.8(15) no
H9A N9 H9B . . . 117.(2) no
C3 N10 H10A . . . 120.5(15) no
C3 N10 H10B . . . 117.0(17) no
H10A N10 H10B . . . 122.(2) no
N4 C1 N1 . . . 112.49(19) no
N4 C1 N5 . . . 119.91(18) no
N1 C1 N5 . . . 127.58(19) no
N3 C2 H2A . . . 109.50 no
N3 C2 H2B . . . 109.50 no
H2A C2 H2B . . . 109.50 no
N3 C2 H2C . . . 109.50 no
H2A C2 H2C . . . 109.50 no
H2B C2 H2C . . . 109.50 no
N10 C3 N8 . . . 120.2(2) no
N10 C3 N9 . . . 121.0(2) no
N8 C3 N9 . . . 118.8(2) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 N3 . . . . 0.6(2) no
N1 N2 N3 N4 . . . . -0.6(2) no
N1 N2 N3 C2 . . . . -179.42(17) no
N2 N3 N4 C1 . . . . 0.3(2) no
C2 N3 N4 C1 . . . . 179.10(17) no
C1 N5 N6 O1 . . . . -178.22(15) no
N3 N4 C1 N1 . . . . 0.1(2) no
N3 N4 C1 N5 . . . . -178.68(17) no
N2 N1 C1 N4 . . . . -0.5(2) no
N2 N1 C1 N5 . . . . 178.21(18) no
N6 N5 C1 N4 . . . . 179.87(17) no
N6 N5 C1 N1 . . . . 1.2(3) no
N7 N8 C3 N10 . . . . -5.7(3) no
N7 N8 C3 N9 . . . . 177.10(19) no
####################################################################### 
# 
# 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_bo3428
_database_code_depnum_ccdc_archive 'CCDC 1431005'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H11 N11 O'
_chemical_formula_weight         217.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   15.703(5)
_cell_length_b                   3.7767(11)
_cell_length_c                   16.028(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.331(5)
_cell_angle_gamma                90.00
_cell_volume                     935.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2781
_cell_measurement_theta_min      2.584
_cell_measurement_theta_max      29.134

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9205
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7676
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         29.11
_reflns_number_total             2503
_reflns_number_gt                1909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0635P)²+0.1500P] 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         2503
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.10974(7) 0.9535(3) 0.31083(6) 0.0271(3) Uani 1 1 d . . .
C1 C 0.31202(9) 0.6087(4) 0.35007(8) 0.0195(3) Uani 1 1 d . . .
C2 C 0.52012(10) 0.2570(4) 0.36990(10) 0.0294(3) Uani 1 1 d . . .
H2A H 0.5459 0.1375 0.4227 0.035 Uiso 1 1 calc R . .
H2B H 0.5568 0.4566 0.3598 0.035 Uiso 1 1 calc R . .
H2C H 0.5154 0.0895 0.3226 0.035 Uiso 1 1 calc R . .
C3 C 0.14766(9) 0.7971(4) 0.59714(8) 0.0185(3) Uani 1 1 d . . .
N1 N 0.32297(8) 0.4813(3) 0.43068(7) 0.0234(3) Uani 1 1 d . . .
N2 N 0.40158(8) 0.3390(3) 0.44617(8) 0.0251(3) Uani 1 1 d . . .
N3 N 0.43440(8) 0.3866(3) 0.37680(8) 0.0231(3) Uani 1 1 d . . .
N4 N 0.38151(8) 0.5530(3) 0.31439(7) 0.0241(3) Uani 1 1 d . . .
N5 N 0.23886(8) 0.7735(3) 0.30447(7) 0.0217(3) Uani 1 1 d . . .
N6 N 0.17989(8) 0.8117(3) 0.35032(8) 0.0232(3) Uani 1 1 d . . .
N7 N 0.01277(8) 0.5788(4) 0.62114(8) 0.0233(3) Uani 1 1 d . . .
H7A H 0.0109(11) 0.383(5) 0.6497(12) 0.032(5) Uiso 1 1 d . . .
N8 N 0.09323(8) 0.7431(4) 0.65073(8) 0.0233(3) Uani 1 1 d . . .
H8 H 0.1059(13) 0.823(6) 0.7022(14) 0.045(6) Uiso 1 1 d . . .
N9 N 0.22225(8) 0.9584(4) 0.62695(8) 0.0239(3) Uani 1 1 d . . .
H9 H 0.2335(13) 1.026(5) 0.6797(13) 0.038(5) Uiso 1 1 d . . .
N10 N 0.28495(9) 1.0378(4) 0.57730(8) 0.0267(3) Uani 1 1 d . . .
H10A H 0.3009(13) 0.840(6) 0.5536(14) 0.047(6) Uiso 1 1 d . . .
H10B H 0.2590(13) 1.185(6) 0.5319(14) 0.047(6) Uiso 1 1 d . . .
N11 N 0.12870(9) 0.6869(4) 0.51721(8) 0.0240(3) Uani 1 1 d . . .
H11A H 0.1629(13) 0.740(5) 0.4794(12) 0.042(6) Uiso 1 1 d . . .
H11B H 0.0761(14) 0.595(5) 0.4990(13) 0.038(5) Uiso 1 1 d . . .
H7B H -0.0282(12) 0.730(5) 0.6311(12) 0.034(5) 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 N6 1.2849(16) . ?
C1 N4 1.3362(18) . ?
C1 N1 1.3604(18) . ?
C1 N5 1.3929(18) . ?
C2 N3 1.4552(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N11 1.3289(18) . ?
C3 N9 1.3305(18) . ?
C3 N8 1.3317(17) . ?
N1 N2 1.3283(18) . ?
N2 N3 1.3188(17) . ?
N3 N4 1.3369(17) . ?
N5 N6 1.2893(16) . ?
N7 N8 1.4112(18) . ?
N7 H7A 0.87(2) . ?
N7 H7B 0.90(2) . ?
N8 H8 0.87(2) . ?
N9 N10 1.4048(16) . ?
N9 H9 0.87(2) . ?
N10 H10A 0.89(2) . ?
N10 H10B 0.95(2) . ?
N11 H11A 0.90(2) . ?
N11 H11B 0.89(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
N4 C1 N1 112.16(12) . . ?
N4 C1 N5 120.38(12) . . ?
N1 C1 N5 127.45(12) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N11 C3 N9 121.34(12) . . ?
N11 C3 N8 121.00(13) . . ?
N9 C3 N8 117.64(12) . . ?
N2 N1 C1 105.98(11) . . ?
N3 N2 N1 106.13(11) . . ?
N2 N3 N4 114.24(12) . . ?
N2 N3 C2 121.66(12) . . ?
N4 N3 C2 124.08(12) . . ?
C1 N4 N3 101.48(11) . . ?
N6 N5 C1 111.11(11) . . ?
O1 N6 N5 113.95(11) . . ?
N8 N7 H7A 108.0(12) . . ?
N8 N7 H7B 106.7(12) . . ?
H7A N7 H7B 110.8(17) . . ?
C3 N8 N7 119.35(12) . . ?
C3 N8 H8 119.7(14) . . ?
N7 N8 H8 120.8(14) . . ?
C3 N9 N10 123.75(12) . . ?
C3 N9 H9 119.7(13) . . ?
N10 N9 H9 116.6(13) . . ?
N9 N10 H10A 109.9(14) . . ?
N9 N10 H10B 108.2(13) . . ?
H10A N10 H10B 106.1(19) . . ?
C3 N11 H11A 121.4(13) . . ?
C3 N11 H11B 118.0(13) . . ?
H11A N11 H11B 119.6(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N1 N2 -0.38(16) . . . . ?
N5 C1 N1 N2 178.22(13) . . . . ?
C1 N1 N2 N3 0.47(15) . . . . ?
N1 N2 N3 N4 -0.42(17) . . . . ?
N1 N2 N3 C2 -178.77(12) . . . . ?
N1 C1 N4 N3 0.13(15) . . . . ?
N5 C1 N4 N3 -178.58(12) . . . . ?
N2 N3 N4 C1 0.18(16) . . . . ?
C2 N3 N4 C1 178.48(13) . . . . ?
N4 C1 N5 N6 -178.24(12) . . . . ?
N1 C1 N5 N6 3.3(2) . . . . ?
C1 N5 N6 O1 -178.12(12) . . . . ?
N11 C3 N8 N7 -2.5(2) . . . . ?
N9 C3 N8 N7 178.83(13) . . . . ?
N11 C3 N9 N10 2.5(2) . . . . ?
N8 C3 N9 N10 -178.85(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050


