# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_1234
_database_code_depnum_ccdc_archive 'CCDC 1540159'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 N10 O'
_chemical_formula_weight         210.19

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           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                   7.5607(8)
_cell_length_b                   13.7150(15)
_cell_length_c                   8.9269(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.388(4)
_cell_angle_gamma                90
_cell_volume                     904.12(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      2.758
_cell_measurement_theta_max      28.344

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(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            13724
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2219
_reflns_number_gt                1640
_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 (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)+(0.0674P)²+0.4096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2219
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.797
_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
N6 N 0.1792(2) 0.45883(12) -0.05056(18) 0.0411(4) Uani 1 1 d . . . . .
N5 N 0.2680(2) 0.43771(11) 0.08270(18) 0.0388(4) Uani 1 1 d D . . . .
O1 O 0.2640(2) 0.36221(11) 0.15813(17) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.4852(2) 0.50594(12) 0.29222(18) 0.0429(4) Uani 1 1 d . . . . .
N9 N -0.1389(2) 0.33841(14) -0.31465(19) 0.0492(4) Uani 1 1 d . . . . .
N7 N 0.0260(2) 0.29798(12) -0.08711(18) 0.0425(4) Uani 1 1 d . . . . .
N4 N 0.4059(2) 0.60059(12) 0.08684(19) 0.0449(4) Uani 1 1 d . . . . .
C2 C 0.3870(2) 0.51480(13) 0.1526(2) 0.0367(4) Uani 1 1 d D . . . .
N8 N -0.0972(2) 0.27080(12) -0.20868(18) 0.0420(4) Uani 1 1 d . . . . .
N10 N -0.0393(2) 0.41514(13) -0.2645(2) 0.0481(4) Uani 1 1 d . . . . .
C3 C 0.0597(2) 0.38846(14) -0.1264(2) 0.0375(4) Uani 1 1 d . . . . .
N2 N 0.5658(2) 0.59227(12) 0.31029(18) 0.0417(4) Uani 1 1 d . . . . .
N3 N 0.5226(2) 0.65022(12) 0.1906(2) 0.0469(4) Uani 1 1 d . . . . .
C4 C -0.1816(4) 0.17450(18) -0.2228(3) 0.0648(7) Uani 1 1 d . . . . .
H4A H -0.2605 0.1683 -0.3221 0.097 Uiso 1 1 calc R U . . .
H4B H -0.2504 0.1667 -0.1449 0.097 Uiso 1 1 calc R U . . .
H4C H -0.0894 0.1253 -0.2108 0.097 Uiso 1 1 calc R U . . .
C1 C 0.6887(3) 0.62194(19) 0.4519(3) 0.0633(7) Uani 1 1 d . . . . .
H1A H 0.7525 0.6797 0.4337 0.095 Uiso 1 1 calc R U . . .
H1B H 0.7739 0.5706 0.4866 0.095 Uiso 1 1 calc R U . . .
H1C H 0.6205 0.6351 0.5289 0.095 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
N6 N5 1.268(2) . ?
N6 C3 1.394(2) . ?
N5 O1 1.239(2) . ?
N5 C2 1.441(2) . ?
N1 C2 1.312(2) . ?
N1 N2 1.326(2) . ?
N9 N8 1.314(2) . ?
N9 N10 1.315(2) . ?
N7 N8 1.323(2) . ?
N7 C3 1.329(3) . ?
N4 N3 1.323(2) . ?
N4 C2 1.336(3) . ?
N8 C4 1.460(3) . ?
N10 C3 1.349(3) . ?
N2 N3 1.315(2) . ?
N2 C1 1.457(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
N5 N6 C3 117.07(16) . . ?
O1 N5 N6 129.13(17) . . ?
O1 N5 C2 117.63(16) . . ?
N6 N5 C2 113.24(15) . . ?
C2 N1 N2 100.63(15) . . ?
N8 N9 N10 106.76(15) . . ?
N8 N7 C3 100.83(15) . . ?
N3 N4 C2 105.28(16) . . ?
N1 C2 N4 114.01(16) . . ?
N1 C2 N5 121.11(16) . . ?
N4 C2 N5 124.86(17) . . ?
N9 N8 N7 114.17(16) . . ?
N9 N8 C4 122.90(17) . . ?
N7 N8 C4 122.92(17) . . ?
N9 N10 C3 105.00(17) . . ?
N7 C3 N10 113.23(17) . . ?
N7 C3 N6 131.25(17) . . ?
N10 C3 N6 115.52(17) . . ?
N3 N2 N1 114.41(16) . . ?
N3 N2 C1 122.49(17) . . ?
N1 N2 C1 123.09(18) . . ?
N2 N3 N4 105.67(15) . . ?
N8 C4 H4A 109.5 . . ?
N8 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N8 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
C3 N6 N5 O1 -0.4(3) . . . . ?
C3 N6 N5 C2 -179.64(14) . . . . ?
N2 N1 C2 N4 0.5(2) . . . . ?
N2 N1 C2 N5 -178.04(15) . . . . ?
N3 N4 C2 N1 -0.3(2) . . . . ?
N3 N4 C2 N5 178.17(16) . . . . ?
O1 N5 C2 N1 -1.2(3) . . . . ?
N6 N5 C2 N1 178.13(16) . . . . ?
O1 N5 C2 N4 -179.57(18) . . . . ?
N6 N5 C2 N4 -0.3(2) . . . . ?
N10 N9 N8 N7 0.5(2) . . . . ?
N10 N9 N8 C4 179.58(19) . . . . ?
C3 N7 N8 N9 -0.6(2) . . . . ?
C3 N7 N8 C4 -179.68(19) . . . . ?
N8 N9 N10 C3 -0.1(2) . . . . ?
N8 N7 C3 N10 0.5(2) . . . . ?
N8 N7 C3 N6 -178.95(18) . . . . ?
N9 N10 C3 N7 -0.2(2) . . . . ?
N9 N10 C3 N6 179.30(15) . . . . ?
N5 N6 C3 N7 -3.8(3) . . . . ?
N5 N6 C3 N10 176.76(16) . . . . ?
C2 N1 N2 N3 -0.5(2) . . . . ?
C2 N1 N2 C1 177.94(19) . . . . ?
N1 N2 N3 N4 0.4(2) . . . . ?
C1 N2 N3 N4 -178.11(19) . . . . ?
C2 N4 N3 N2 0.0(2) . . . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

