# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_Kuwar
_database_code_depnum_ccdc_archive 'CCDC 1524229'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N4 O2'
_chemical_formula_sum            'C20 H16 N4 O2'
_chemical_formula_weight         344.372

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                   8.473(5)
_cell_length_b                   5.922(5)
_cell_length_c                   15.324(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.525(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     768.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4646
_cell_measurement_theta_min      0.881
_cell_measurement_theta_max      0.915

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   0.881
_exptl_transmission_factor_max   0.915
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.759
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4635
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.22
_diffrn_reflns_theta_max         72.83
_diffrn_reflns_theta_full        72.83
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1492
_reflns_number_gt                1253
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (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)+(0.1000P)²+0.5513P] 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         1492
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2223
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_restrained_S_all      1.256
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

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 0.5496(3) 0.0696(4) 0.63539(16) 0.0279(6) Uani 1 1 d . . . . .
C6 C 0.6492(3) 0.2557(4) 0.62273(16) 0.0302(6) Uani 1 1 d . . . . .
C5 C 0.7939(3) 0.2720(5) 0.66576(17) 0.0360(7) Uani 1 1 d . . . . .
H5 H 0.858327 0.397062 0.657691 0.043 Uiso 1 1 calc R U . . .
C10 C -0.0325(3) 0.1996(4) 0.45591(17) 0.0324(6) Uani 1 1 d . . . . .
H10 H -0.054268 0.333542 0.426267 0.039 Uiso 1 1 calc R U . . .
N2 N 0.4041(2) 0.0891(4) 0.58965(13) 0.0291(6) Uani 1 1 d . . . . .
C9 C 0.1126(3) 0.1705(5) 0.49766(17) 0.0323(6) Uani 1 1 d . . . . .
H9 H 0.187592 0.285019 0.495979 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2996(3) -0.0640(4) 0.58789(17) 0.0311(6) Uani 1 1 d . . . . .
H11 H 0.319758 -0.200586 0.615998 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8416(3) 0.0987(5) 0.72122(18) 0.0398(7) Uani 1 1 d . . . . .
H4 H 0.940129 0.105965 0.749256 0.048 Uiso 1 1 calc R U . . .
O1 O 0.5999(2) 0.4211(3) 0.56714(14) 0.0424(6) Uani 1 1 d . . . . .
H1 H 0.511316 0.390774 0.547687 0.064 Uiso 1 1 calc R U . . .
C3 C 0.7447(3) -0.0852(5) 0.73553(19) 0.0384(7) Uani 1 1 d . . . . .
H3 H 0.776868 -0.198118 0.774262 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1475(3) -0.0289(5) 0.54222(16) 0.0295(6) Uani 1 1 d . . . . .
C2 C 0.6000(3) -0.1005(5) 0.69210(17) 0.0345(7) Uani 1 1 d . . . . .
H2 H 0.535867 -0.225518 0.700883 0.041 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
C1 C2 1.390(4) . ?
C1 C6 1.405(4) . ?
C1 N2 1.407(3) . ?
C6 O1 1.357(3) . ?
C6 C5 1.380(4) . ?
C5 C4 1.386(4) . ?
C10 C9 1.382(4) . ?
C10 C8 1.405(4) 3_556 ?
N2 C11 1.267(3) . ?
C9 C8 1.392(4) . ?
C11 C8 1.465(4) . ?
C4 C3 1.385(4) . ?
C3 C2 1.382(4) . ?
C8 C10 1.405(4) 3_556 ?

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
C2 C1 C6 118.7(2) . . ?
C2 C1 N2 128.4(2) . . ?
C6 C1 N2 112.8(2) . . ?
O1 C6 C5 120.3(2) . . ?
O1 C6 C1 118.5(2) . . ?
C5 C6 C1 121.2(2) . . ?
C6 C5 C4 118.8(3) . . ?
C9 C10 C8 120.7(3) . 3_556 ?
C11 N2 C1 123.7(2) . . ?
C10 C9 C8 120.5(2) . . ?
N2 C11 C8 120.9(2) . . ?
C3 C4 C5 121.0(2) . . ?
C2 C3 C4 119.8(3) . . ?
C9 C8 C10 118.8(2) . 3_556 ?
C9 C8 C11 121.8(2) . . ?
C10 C8 C11 119.3(2) 3_556 . ?
C3 C2 C1 120.5(2) . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.147

