# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_3l
_database_code_depnum_ccdc_archive 'CCDC 1578045'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;


#mo_v433_GuillotICMMO

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N6 O'
_chemical_formula_sum            'C12 H14 N6 O'
_chemical_formula_weight         258.29

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      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                   8.3805(7)
_cell_length_b                   8.9419(8)
_cell_length_c                   9.0849(7)
_cell_angle_alpha                103.317(3)
_cell_angle_beta                 107.305(3)
_cell_angle_gamma                98.863(4)
_cell_volume                     614.08(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2729
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.38

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13706
_diffrn_reflns_av_unetI/netI     0.2330
_diffrn_reflns_av_R_equivalents  0.3305
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2165
_reflns_number_gt                1129
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0143P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2165
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_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
C1 C 0.7197(3) 0.6521(3) 0.1519(3) 0.0180(6) Uani 1 1 d . . . . .
H1 H 0.821431 0.617395 0.152250 0.022 Uiso 1 1 calc R U . . .
C2 C 0.6403(3) 0.7068(3) 0.0263(3) 0.0181(6) Uani 1 1 d . . . . .
H2 H 0.683759 0.710709 -0.058500 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4928(3) 0.7557(3) 0.0318(3) 0.0155(6) Uani 1 1 d . . . . .
H3 H 0.434084 0.794620 -0.052611 0.019 Uiso 1 1 calc R U . . .
C4 C 0.5172(3) 0.6951(3) 0.2651(3) 0.0126(6) Uani 1 1 d . . . . .
C5 C 0.2795(3) 0.6959(3) 0.3726(3) 0.0123(6) Uani 1 1 d . . . . .
C6 C 0.2520(3) 0.8657(3) 0.3938(3) 0.0163(6) Uani 1 1 d . . . . .
H6A H 0.132661 0.869625 0.336928 0.020 Uiso 1 1 calc R U . . .
H6B H 0.336240 0.937537 0.369333 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2939(3) 0.8858(3) 0.5765(3) 0.0208(6) Uani 1 1 d . . . . .
H7A H 0.414905 0.940589 0.643419 0.025 Uiso 1 1 calc R U . . .
H7B H 0.213015 0.933451 0.621329 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2570(3) 0.7055(3) 0.5384(3) 0.0138(6) Uani 1 1 d . . . . .
H8 H 0.134862 0.659590 0.524083 0.017 Uiso 1 1 calc R U . . .
C9 C 0.1036(2) 0.4242(3) 0.2185(3) 0.0117(6) Uani 1 1 d . . . . .
C10 C -0.0720(3) 0.1831(3) 0.0680(3) 0.0145(6) Uani 1 1 d . . . . .
H10 H -0.158909 0.116239 -0.028605 0.017 Uiso 1 1 calc R U . . .
C11 C -0.0093(3) 0.1187(3) 0.1909(3) 0.0153(6) Uani 1 1 d . . . . .
H11 H -0.050203 0.010671 0.181846 0.018 Uiso 1 1 calc R U . . .
C12 C 0.1160(3) 0.2210(3) 0.3274(3) 0.0156(6) Uani 1 1 d . . . . .
H12 H 0.162818 0.180273 0.414381 0.019 Uiso 1 1 calc R U . . .
N1 N 0.6630(2) 0.6445(2) 0.2737(2) 0.0148(5) Uani 1 1 d . . . . .
N2 N 0.4283(2) 0.7514(2) 0.1488(2) 0.0132(5) Uani 1 1 d . . . . .
N3 N 0.4562(2) 0.6890(2) 0.3874(2) 0.0131(5) Uani 1 1 d . . . . .
N4 N 0.1523(2) 0.5796(2) 0.2310(2) 0.0130(5) Uani 1 1 d . . . . .
N5 N 0.1767(2) 0.3743(2) 0.3461(2) 0.0126(5) Uani 1 1 d . . . . .
N6 N -0.0173(2) 0.3344(2) 0.0770(2) 0.0128(5) Uani 1 1 d . . . . .
O1 O 0.37168(18) 0.65126(19) 0.64977(18) 0.0210(4) Uani 1 1 d . . . . .
H100 H 0.3260(18) 0.545(3) 0.6360(19) 0.031 Uiso 1 1 calc R U . . .
H30 H 0.506(3) 0.641(3) 0.458(3) 0.033(7) Uiso 1 1 d . . . . .
H4 H 0.113(3) 0.605(3) 0.141(3) 0.037(8) 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
C1 N1 1.339(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.333(3) . ?
C3 H3 0.9500 . ?
C4 N2 1.347(2) . ?
C4 N1 1.354(2) . ?
C4 N3 1.363(3) . ?
C5 N4 1.449(3) . ?
C5 N3 1.459(2) . ?
C5 C6 1.548(3) . ?
C5 C8 1.557(3) . ?
C6 C7 1.551(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.405(2) . ?
C8 H8 1.0000 . ?
C9 N5 1.349(3) . ?
C9 N6 1.350(3) . ?
C9 N4 1.355(3) . ?
C10 N6 1.335(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9500 . ?
C12 N5 1.339(3) . ?
C12 H12 0.9500 . ?
N3 H30 0.89(2) . ?
N4 H4 0.88(2) . ?
O1 H100 0.93(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
N1 C1 C2 124.2(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 115.4(2) . . ?
C1 C2 H2 122.3 . . ?
C3 C2 H2 122.3 . . ?
N2 C3 C2 123.8(2) . . ?
N2 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N2 C4 N1 126.5(2) . . ?
N2 C4 N3 117.34(19) . . ?
N1 C4 N3 116.15(19) . . ?
N4 C5 N3 113.33(18) . . ?
N4 C5 C6 113.67(15) . . ?
N3 C5 C6 112.90(19) . . ?
N4 C5 C8 117.71(19) . . ?
N3 C5 C8 109.02(16) . . ?
C6 C5 C8 87.76(17) . . ?
C5 C6 C7 88.60(16) . . ?
C5 C6 H6A 113.9 . . ?
C7 C6 H6A 113.9 . . ?
C5 C6 H6B 113.9 . . ?
C7 C6 H6B 113.9 . . ?
H6A C6 H6B 111.1 . . ?
C8 C7 C6 88.59(17) . . ?
C8 C7 H7A 113.9 . . ?
C6 C7 H7A 113.9 . . ?
C8 C7 H7B 113.9 . . ?
C6 C7 H7B 113.9 . . ?
H7A C7 H7B 111.1 . . ?
O1 C8 C7 114.11(19) . . ?
O1 C8 C5 118.66(17) . . ?
C7 C8 C5 89.01(17) . . ?
O1 C8 H8 111.1 . . ?
C7 C8 H8 111.1 . . ?
C5 C8 H8 111.1 . . ?
N5 C9 N6 126.4(2) . . ?
N5 C9 N4 118.1(2) . . ?
N6 C9 N4 115.4(2) . . ?
N6 C10 C11 123.6(2) . . ?
N6 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 C10 115.6(2) . . ?
C12 C11 H11 122.2 . . ?
C10 C11 H11 122.2 . . ?
N5 C12 C11 124.32(19) . . ?
N5 C12 H12 117.8 . . ?
C11 C12 H12 117.8 . . ?
C1 N1 C4 114.71(18) . . ?
C3 N2 C4 115.35(19) . . ?
C4 N3 C5 121.82(18) . . ?
C4 N3 H30 117.9(15) . . ?
C5 N3 H30 115.5(15) . . ?
C9 N4 C5 124.18(19) . . ?
C9 N4 H4 115.5(16) . . ?
C5 N4 H4 119.7(16) . . ?
C12 N5 C9 114.64(19) . . ?
C10 N6 C9 115.38(19) . . ?
C8 O1 H100 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.064

