# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1915619'
loop_
_audit_author_name
_audit_author_address
'Sonia Barroso'
;UCIBIO Applied Molecular Biosciences Unit
Portugal
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H9 N3 O'
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      110(2)
_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 2yn'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   24.8320(8)
_cell_length_b                   7.2057(3)
_cell_length_c                   12.0342(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.7530(10)
_cell_angle_gamma                90
_cell_volume                     2038.99(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7811
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      25.69
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            16950
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.466
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1931
_reflns_number_gt                1693
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP and Mercury'
_computing_publication_material  'WingX and enCIFer'
_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)+(0.0538P)²+1.4289P] 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         1931
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
N2 N 0.96024(4) 0.22108(15) 0.10509(9) 0.0138(2) Uani 1 1 d . . . . .
O1 O 1.11003(4) 0.43235(14) 0.06589(8) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.86044(5) 0.04454(19) -0.17249(11) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.857581 0.020564 -0.250112 0.022 Uiso 1 1 calc R U . . .
N3 N 0.86933(4) 0.10983(15) 0.06321(9) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.77433(5) 0.01135(18) 0.02694(11) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.91329(5) 0.14950(17) 0.02335(10) 0.0134(3) Uani 1 1 d . . . . .
N1 N 1.05102(4) 0.32711(15) 0.16404(9) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.91081(5) 0.11951(17) -0.09430(11) 0.0154(3) Uani 1 1 d . . . . .
C4 C 1.00580(5) 0.24077(18) -0.04453(11) 0.0174(3) Uani 1 1 d . . . . .
H4 H 1.037588 0.274657 -0.064702 0.021 Uiso 1 1 calc R U . . .
C5 C 0.95912(5) 0.16840(18) -0.12544(11) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.958929 0.150802 -0.202126 0.021 Uiso 1 1 calc R U . . .
C3 C 1.00469(5) 0.26341(17) 0.07252(11) 0.0141(3) Uani 1 1 d . . . . .
C10 C 0.82208(5) 0.04398(18) -0.01408(11) 0.0161(3) Uani 1 1 d . . . . .
C1 C 1.10010(5) 0.40795(18) 0.15802(11) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.81606(5) 0.00770(19) -0.13295(11) 0.0193(3) Uani 1 1 d . . . . .
H9 H 0.782275 -0.040581 -0.183279 0.023 Uiso 1 1 calc R U . . .
C2 C 1.14113(6) 0.4644(2) 0.27428(12) 0.0232(3) Uani 1 1 d . . . . .
H2A H 1.167368 0.364929 0.305327 0.035 Uiso 1 1 calc R U . . .
H2B H 1.120623 0.491909 0.327673 0.035 Uiso 1 1 calc R U . . .
H2C H 1.161676 0.572599 0.264347 0.035 Uiso 1 1 calc R U . . .
C12 C 0.73283(5) -0.0130(2) 0.05342(12) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.700277 -0.032171 0.074194 0.028 Uiso 1 1 calc R U . . .
H1 H 1.0471(6) 0.309(2) 0.2343(14) 0.018(4) 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
N2 C3 1.3205(15) . ?
N2 C7 1.3620(16) . ?
O1 C1 1.2235(16) . ?
C8 C9 1.3596(18) . ?
C8 C6 1.4089(18) . ?
C8 H8 0.9300 . ?
N3 C10 1.3286(16) . ?
N3 C7 1.3566(15) . ?
C11 C12 1.1855(18) . ?
C11 C10 1.4428(17) . ?
C7 C6 1.4139(17) . ?
N1 C1 1.3735(16) . ?
N1 C3 1.3901(16) . ?
N1 H1 0.891(16) . ?
C6 C5 1.4117(17) . ?
C4 C5 1.3557(18) . ?
C4 C3 1.4270(17) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C10 C9 1.4140(18) . ?
C1 C2 1.4982(18) . ?
C9 H9 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C12 H12 0.9300 . ?

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
C3 N2 C7 118.44(10) . . ?
C9 C8 C6 119.12(11) . . ?
C9 C8 H8 120.4 . . ?
C6 C8 H8 120.4 . . ?
C10 N3 C7 117.23(10) . . ?
C12 C11 C10 175.71(13) . . ?
N3 C7 N2 115.06(10) . . ?
N3 C7 C6 122.74(11) . . ?
N2 C7 C6 122.19(11) . . ?
C1 N1 C3 128.36(11) . . ?
C1 N1 H1 118.7(9) . . ?
C3 N1 H1 112.9(9) . . ?
C8 C6 C5 124.49(11) . . ?
C8 C6 C7 118.10(11) . . ?
C5 C6 C7 117.41(11) . . ?
C5 C4 C3 118.01(11) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 120.57(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N2 C3 N1 113.52(10) . . ?
N2 C3 C4 123.35(11) . . ?
N1 C3 C4 123.10(11) . . ?
N3 C10 C9 123.83(11) . . ?
N3 C10 C11 117.17(11) . . ?
C9 C10 C11 118.99(11) . . ?
O1 C1 N1 123.34(12) . . ?
O1 C1 C2 122.18(11) . . ?
N1 C1 C2 114.49(11) . . ?
C8 C9 C10 118.94(12) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C11 C12 H12 180.0 . . ?

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
C10 N3 C7 N2 178.38(11) . . . . ?
C10 N3 C7 C6 -1.48(18) . . . . ?
C3 N2 C7 N3 -179.87(10) . . . . ?
C3 N2 C7 C6 -0.01(18) . . . . ?
C9 C8 C6 C5 -178.17(12) . . . . ?
C9 C8 C6 C7 1.34(19) . . . . ?
N3 C7 C6 C8 -0.26(19) . . . . ?
N2 C7 C6 C8 179.89(11) . . . . ?
N3 C7 C6 C5 179.28(11) . . . . ?
N2 C7 C6 C5 -0.57(18) . . . . ?
C3 C4 C5 C6 0.78(19) . . . . ?
C8 C6 C5 C4 179.65(12) . . . . ?
C7 C6 C5 C4 0.14(19) . . . . ?
C7 N2 C3 N1 -177.17(10) . . . . ?
C7 N2 C3 C4 1.03(18) . . . . ?
C1 N1 C3 N2 -169.36(12) . . . . ?
C1 N1 C3 C4 12.4(2) . . . . ?
C5 C4 C3 N2 -1.43(19) . . . . ?
C5 C4 C3 N1 176.59(12) . . . . ?
C7 N3 C10 C9 2.23(19) . . . . ?
C7 N3 C10 C11 -176.73(11) . . . . ?
C3 N1 C1 O1 -1.4(2) . . . . ?
C3 N1 C1 C2 178.74(12) . . . . ?
C6 C8 C9 C10 -0.68(19) . . . . ?
N3 C10 C9 C8 -1.2(2) . . . . ?
C11 C10 C9 C8 177.76(12) . . . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
