# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_B
_database_code_depnum_ccdc_archive 'CCDC 1486515'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N3 O3'
_chemical_formula_weight         211.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   26.518(14)
_cell_length_b                   6.018(3)
_cell_length_c                   18.911(8)
_cell_angle_alpha                90
_cell_angle_beta                 134.50(2)
_cell_angle_gamma                90
_cell_volume                     2152.5(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2070
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   0.4805
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4250
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_av_R_equivalents  0.1035
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.154
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1992
_reflns_number_gt                1366
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1313P)²+3.7213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1992
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.2175
_refine_ls_wR_factor_gt          0.1744
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
N1 N 0.05035(12) 0.2511(4) 0.11440(17) 0.0219(6) Uani 1 1 d . . . . .
H1 H 0.0469 0.1370 0.0805 0.033 Uiso 1 1 d R U . . .
N2 N 0.11148(12) 0.3358(4) 0.19808(17) 0.0238(6) Uani 1 1 d . . . . .
N3 N -0.13685(12) 0.4025(4) -0.06851(17) 0.0218(6) Uani 1 1 d . . . . .
C1 C -0.20357(15) 0.3036(6) -0.1583(2) 0.0310(8) Uani 1 1 d . . . . .
H1A H -0.2083 0.3253 -0.2131 0.047 Uiso 1 1 calc R U . . .
H1B H -0.2424 0.3733 -0.1726 0.047 Uiso 1 1 calc R U . . .
H1C H -0.2035 0.1473 -0.1480 0.047 Uiso 1 1 calc R U . . .
C2 C -0.14103(17) 0.6219(5) -0.0399(3) 0.0326(8) Uani 1 1 d . . . . .
H2A H -0.1321 0.6091 0.0187 0.049 Uiso 1 1 calc R U . . .
H2B H -0.1874 0.6828 -0.0928 0.049 Uiso 1 1 calc R U . . .
H2C H -0.1064 0.7182 -0.0268 0.049 Uiso 1 1 calc R U . . .
C3 C -0.07697(14) 0.2870(5) -0.0192(2) 0.0190(6) Uani 1 1 d . . . . .
C4 C -0.00743(14) 0.3747(5) 0.07468(19) 0.0188(6) Uani 1 1 d . . . . .
C5 C 0.01795(15) 0.5517(5) 0.1392(2) 0.0229(7) Uani 1 1 d . . . . .
H5 H -0.0080 0.6659 0.1344 0.027 Uiso 1 1 calc R U . . .
C6 C 0.09145(15) 0.5202(5) 0.2133(2) 0.0214(7) Uani 1 1 d . . . . .
C7 C 0.14601(15) 0.6593(5) 0.3012(2) 0.0243(7) Uani 1 1 d . . . . .
C8 C 0.16280(18) 0.9880(6) 0.3857(2) 0.0330(8) Uani 1 1 d . . . . .
H8A H 0.1868 1.0747 0.3734 0.040 Uiso 1 1 calc R U . . .
H8B H 0.1980 0.9123 0.4487 0.040 Uiso 1 1 calc R U . . .
C9 C 0.1177(2) 1.1368(6) 0.3872(3) 0.0425(9) Uani 1 1 d . . . . .
H9A H 0.0826 1.2086 0.3241 0.064 Uiso 1 1 calc R U . . .
H9B H 0.1470 1.2471 0.4381 0.064 Uiso 1 1 calc R U . . .
H9C H 0.0948 1.0492 0.4005 0.064 Uiso 1 1 calc R U . . .
O1 O -0.07696(11) 0.1017(4) -0.04877(17) 0.0319(6) Uani 1 1 d . . . . .
O2 O 0.20887(11) 0.6300(4) 0.35989(16) 0.0364(6) Uani 1 1 d . . . . .
O3 O 0.11529(11) 0.8278(4) 0.30632(15) 0.0306(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.340(3) . ?
N1 C4 1.361(4) . ?
N1 H1 0.9000 . ?
N2 C6 1.345(4) . ?
N3 C3 1.341(4) . ?
N3 C2 1.460(4) . ?
N3 C1 1.469(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O1 1.248(4) . ?
C3 C4 1.497(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.404(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.479(4) . ?
C7 O2 1.203(4) . ?
C7 O3 1.346(4) . ?
C8 O3 1.456(4) . ?
C8 C9 1.511(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
N2 N1 C4 113.9(2) . . ?
N2 N1 H1 124.5 . . ?
C4 N1 H1 120.8 . . ?
N1 N2 C6 103.5(2) . . ?
C3 N3 C2 124.8(2) . . ?
C3 N3 C1 118.3(2) . . ?
C2 N3 C1 116.9(2) . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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 . . ?
O1 C3 N3 121.6(3) . . ?
O1 C3 C4 117.4(3) . . ?
N3 C3 C4 121.1(3) . . ?
N1 C4 C5 105.7(2) . . ?
N1 C4 C3 115.9(2) . . ?
C5 C4 C3 138.5(3) . . ?
C4 C5 C6 104.6(2) . . ?
C4 C5 H5 127.7 . . ?
C6 C5 H5 127.7 . . ?
N2 C6 C5 112.2(3) . . ?
N2 C6 C7 119.1(3) . . ?
C5 C6 C7 128.7(3) . . ?
O2 C7 O3 124.2(3) . . ?
O2 C7 C6 125.8(3) . . ?
O3 C7 C6 110.0(2) . . ?
O3 C8 C9 106.7(3) . . ?
O3 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O3 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 O3 C8 116.3(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
C4 N1 N2 C6 1.2(3) . . . . ?
C2 N3 C3 O1 -178.6(3) . . . . ?
C1 N3 C3 O1 1.2(4) . . . . ?
C2 N3 C3 C4 2.2(4) . . . . ?
C1 N3 C3 C4 -178.0(2) . . . . ?
N2 N1 C4 C5 -1.6(3) . . . . ?
N2 N1 C4 C3 179.8(2) . . . . ?
O1 C3 C4 N1 5.4(4) . . . . ?
N3 C3 C4 N1 -175.4(2) . . . . ?
O1 C3 C4 C5 -172.6(3) . . . . ?
N3 C3 C4 C5 6.6(5) . . . . ?
N1 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
N1 N2 C6 C5 -0.2(3) . . . . ?
N1 N2 C6 C7 179.7(2) . . . . ?
C4 C5 C6 N2 -0.7(3) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
N2 C6 C7 O2 4.1(5) . . . . ?
C5 C6 C7 O2 -176.0(3) . . . . ?
N2 C6 C7 O3 -176.5(2) . . . . ?
C5 C6 C7 O3 3.4(4) . . . . ?
O2 C7 O3 C8 3.4(4) . . . . ?
C6 C7 O3 C8 -176.0(2) . . . . ?
C9 C8 O3 C7 -170.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8B O2 0.97 2.59 3.505(4) 156.3 7_566
C2 H2C O1 0.96 2.56 3.413(4) 147.9 1_565
C2 H2B O2 0.96 2.49 3.330(4) 146.4 8_465
N1 H1 O1 0.90 1.93 2.788(3) 158.8 5
N1 H1 O1 0.90 1.93 2.788(3) 158.8 5
C2 H2B O2 0.96 2.49 3.330(4) 146.4 8_465
C2 H2C O1 0.96 2.56 3.413(4) 147.9 1_565
C8 H8B O2 0.97 2.59 3.505(4) 156.3 7_566

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.109

_shelxl_version_number           2014/6

