# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_TEST77_a
_database_code_depnum_ccdc_archive 'CCDC 1861149'
_audit_update_record             
;
2018-08-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N6 O'
_chemical_formula_weight         292.31

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                   19.810(9)
_cell_length_b                   4.548(2)
_cell_length_c                   16.353(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.47(3)
_cell_angle_gamma                90
_cell_volume                     1420.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    2458
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.70

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .983
_exptl_absorpt_correction_T_max  .987
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5944
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_limit_h_min       -23
_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       18
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1248
_reflns_number_gt                1048
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0420P)²+2.5124P] 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         1248
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
O001 O 0.500000 0.2452(4) 0.750000 0.0247(5) Uani 1 2 d S T P . .
N002 N 0.62003(8) 0.5345(4) 0.75116(11) 0.0209(4) Uani 1 1 d . . . . .
H002 H 0.653646 0.523748 0.798716 0.025 Uiso 1 1 calc R U . . .
N003 N 0.55744(9) 0.6774(4) 0.74824(12) 0.0229(5) Uani 1 1 d . . . . .
H003 H 0.554940 0.870416 0.745292 0.028 Uiso 1 1 calc R U . . .
N004 N 0.66961(10) -0.0978(5) 0.39784(13) 0.0335(5) Uani 1 1 d . . . . .
C005 C 0.62800(10) 0.4092(4) 0.67695(13) 0.0192(5) Uani 1 1 d . . . . .
C006 C 0.68023(10) 0.1953(4) 0.68377(13) 0.0199(5) Uani 1 1 d . . . . .
H006 H 0.707491 0.134831 0.738177 0.024 Uiso 1 1 calc R U . . .
C007 C 0.500000 0.5155(6) 0.750000 0.0191(6) Uani 1 2 d S T P . .
C008 C 0.65244(11) 0.1612(5) 0.53170(14) 0.0223(5) Uani 1 1 d . . . . .
C009 C 0.58893(10) 0.4989(5) 0.59649(14) 0.0235(5) Uani 1 1 d . . . . .
H009 H 0.553939 0.645759 0.591328 0.028 Uiso 1 1 calc R U . . .
C00A C 0.69215(11) 0.0725(4) 0.61187(13) 0.0217(5) Uani 1 1 d . . . . .
H00C H 0.727462 -0.072779 0.616838 0.026 Uiso 1 1 calc R U . . .
C00B C 0.60078(11) 0.3759(5) 0.52474(14) 0.0245(5) Uani 1 1 d . . . . .
H00D H 0.573776 0.437217 0.470292 0.029 Uiso 1 1 calc R U . . .
C00C C 0.66242(11) 0.0212(5) 0.45709(15) 0.0259(5) 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
O001 C007 1.229(3) . ?
N002 C005 1.387(3) . ?
N002 N003 1.389(2) . ?
N002 H002 0.8800 . ?
N003 C007 1.362(2) . ?
N003 H003 0.8800 . ?
N004 C00C 1.152(3) . ?
C005 C009 1.398(3) . ?
C005 C006 1.403(3) . ?
C006 C00A 1.378(3) . ?
C006 H006 0.9500 . ?
C008 C00A 1.396(3) . ?
C008 C00B 1.397(3) . ?
C008 C00C 1.436(3) . ?
C009 C00B 1.375(3) . ?
C009 H009 0.9500 . ?
C00A H00C 0.9500 . ?
C00B H00D 0.9500 . ?

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
C005 N002 N003 118.10(17) . . ?
C005 N002 H002 121.0 . . ?
N003 N002 H002 121.0 . . ?
C007 N003 N002 119.29(17) . . ?
C007 N003 H003 120.4 . . ?
N002 N003 H003 120.4 . . ?
N002 C005 C009 122.67(19) . . ?
N002 C005 C006 117.97(19) . . ?
C009 C005 C006 119.26(19) . . ?
C00A C006 C005 120.3(2) . . ?
C00A C006 H006 119.9 . . ?
C005 C006 H006 119.9 . . ?
O001 C007 N003 122.73(12) . 2_656 ?
O001 C007 N003 122.72(12) . . ?
N003 C007 N003 114.5(2) 2_656 . ?
C00A C008 C00B 119.70(19) . . ?
C00A C008 C00C 119.92(19) . . ?
C00B C008 C00C 120.3(2) . . ?
C00B C009 C005 120.44(19) . . ?
C00B C009 H009 119.8 . . ?
C005 C009 H009 119.8 . . ?
C006 C00A C008 120.15(19) . . ?
C006 C00A H00C 119.9 . . ?
C008 C00A H00C 119.9 . . ?
C009 C00B C008 120.2(2) . . ?
C009 C00B H00D 119.9 . . ?
C008 C00B H00D 119.9 . . ?
N004 C00C C008 178.1(2) . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.049

