# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_red
# publcif _publ_body_element loop end

_audit_update_record             
;
2013-10-15 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N4 O2'
_chemical_formula_weight         332.36

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.3809(14)
_cell_length_b                   5.5940(4)
_cell_length_c                   15.3584(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.915(4)
_cell_angle_gamma                90.00
_cell_volume                     1683.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11617
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3240
_reflns_number_gt                1964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for negative
F². The threshold expression of F² > 2sigma(F²) is used only for
calculating R-factors(gt) etc. and is not relevant to the
choice of reflections for refinement. R-factors based on F² are
statistically about twice as large as those based on F, and R-- factors based
on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42202(6) 0.9355(3) 0.08344(10) 0.0445(4) Uani 1 1 d . . .
O2 O 0.74408(9) 0.8960(4) 0.23546(14) 0.0905(7) Uani 1 1 d . . .
C1 C 0.12290(10) 1.0006(4) -0.00207(14) 0.0406(6) Uani 1 1 d . . .
N3 N 0.21759(8) 0.8636(3) -0.05852(12) 0.0412(5) Uani 1 1 d . . .
N1 N 0.28348(9) 0.5605(4) -0.03142(14) 0.0569(6) Uani 1 1 d . . .
N2 N 0.04135(12) 1.0048(5) 0.30081(17) 0.0789(8) Uani 1 1 d . . .
C4 C 0.05630(11) 1.0039(5) 0.23474(18) 0.0544(6) Uani 1 1 d . . .
C5 C 0.07738(10) 1.0045(4) 0.15206(15) 0.0437(6) Uani 1 1 d . . .
C6 C 0.05962(11) 0.8177(4) 0.09081(16) 0.0495(6) Uani 1 1 d . . .
H6 H 0.0322 0.6938 0.1011 0.059 Uiso 1 1 calc R . .
C7 C 0.08273(10) 0.8168(4) 0.01498(15) 0.0456(6) Uani 1 1 d . . .
H7 H 0.0712 0.6905 -0.0257 0.055 Uiso 1 1 calc R . .
C8 C 0.15203(10) 0.9905(4) -0.08231(15) 0.0474(6) Uani 1 1 d . . .
H8A H 0.1202 0.9091 -0.1321 0.057 Uiso 1 1 calc R . .
H8B H 0.1585 1.1516 -0.1018 0.057 Uiso 1 1 calc R . .
C9 C 0.28079(10) 0.9536(4) -0.02611(15) 0.0417(6) Uani 1 1 d . . .
C10 C 0.32221(10) 0.7583(4) -0.00921(14) 0.0387(5) Uani 1 1 d . . .
C11 C 0.39764(10) 0.7384(4) 0.02447(15) 0.0434(6) Uani 1 1 d . . .
H11A H 0.4101 0.5890 0.0569 0.052 Uiso 1 1 calc R . .
H11B H 0.4177 0.7414 -0.0259 0.052 Uiso 1 1 calc R . .
C12 C 0.49104(10) 0.9541(4) 0.12043(13) 0.0372(5) Uani 1 1 d . . .
C13 C 0.51304(11) 1.1511(4) 0.17551(14) 0.0436(6) Uani 1 1 d . . .
H13 H 0.4814 1.2605 0.1852 0.052 Uiso 1 1 calc R . .
C14 C 0.58188(11) 1.1854(4) 0.21605(14) 0.0464(6) Uani 1 1 d . . .
H14 H 0.5963 1.3193 0.2521 0.056 Uiso 1 1 calc R . .
C15 C 0.62999(10) 1.0211(4) 0.20342(14) 0.0427(6) Uani 1 1 d . . .
C16 C 0.70482(12) 1.0522(5) 0.24459(15) 0.0544(7) Uani 1 1 d . . .
C17 C 0.73203(13) 1.2771(6) 0.29333(19) 0.0778(9) Uani 1 1 d . . .
H17A H 0.7773 1.2494 0.3315 0.117 Uiso 1 1 calc R . .
H17B H 0.7030 1.3269 0.3297 0.117 Uiso 1 1 calc R . .
H17C H 0.7334 1.3997 0.2501 0.117 Uiso 1 1 calc R . .
N18 N 0.21894(9) 0.6249(4) -0.06172(15) 0.0611(6) Uani 1 1 d . . .
C19 C 0.11674(11) 1.1914(4) 0.13516(17) 0.0535(6) Uani 1 1 d . . .
H19 H 0.1279 1.3187 0.1755 0.064 Uiso 1 1 calc R . .
C1A C 0.13930(11) 1.1883(4) 0.05866(17) 0.0517(6) Uani 1 1 d . . .
H1A H 0.1659 1.3137 0.0476 0.062 Uiso 1 1 calc R . .
C1B C 0.53850(10) 0.7898(4) 0.10720(15) 0.0432(6) Uani 1 1 d . . .
H1B H 0.5243 0.6569 0.0705 0.052 Uiso 1 1 calc R . .
C20 C 0.60680(11) 0.8252(4) 0.14891(15) 0.0464(6) Uani 1 1 d . . .
H20 H 0.6383 0.7139 0.1401 0.056 Uiso 1 1 calc R . .
H9 H 0.2896(11) 1.132(5) -0.0154(15) 0.065(7) 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
O1 C12 1.369(2) . ?
O1 C11 1.427(3) . ?
O2 C16 1.218(3) . ?
C1 C1A 1.383(3) . ?
C1 C7 1.383(3) . ?
C1 C8 1.509(3) . ?
N3 N18 1.337(3) . ?
N3 C9 1.345(3) . ?
N3 C8 1.468(3) . ?
N1 N18 1.319(2) . ?
N1 C10 1.348(3) . ?
N2 C4 1.137(3) . ?
C4 C5 1.448(3) . ?
C5 C19 1.385(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.361(3) . ?
C9 H9 1.02(3) . ?
C10 C11 1.486(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.387(3) . ?
C12 C1B 1.389(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.381(3) . ?
C15 C16 1.492(3) . ?
C16 C17 1.491(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 C1A 1.374(3) . ?
C19 H19 0.9300 . ?
C1A H1A 0.9300 . ?
C1B C20 1.378(3) . ?
C1B H1B 0.9300 . ?
C20 H20 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
C12 O1 C11 117.48(15) . . ?
C1A C1 C7 118.9(2) . . ?
C1A C1 C8 120.2(2) . . ?
C7 C1 C8 120.8(2) . . ?
N18 N3 C9 111.12(17) . . ?
N18 N3 C8 120.04(17) . . ?
C9 N3 C8 128.7(2) . . ?
N18 N1 C10 108.86(18) . . ?
N2 C4 C5 178.3(3) . . ?
C19 C5 C6 119.9(2) . . ?
C19 C5 C4 119.5(2) . . ?
C6 C5 C4 120.6(2) . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C1 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
C1 C7 H7 119.4 . . ?
N3 C8 C1 110.49(17) . . ?
N3 C8 H8A 109.6 . . ?
C1 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C1 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 C10 104.5(2) . . ?
N3 C9 H9 122.3(12) . . ?
C10 C9 H9 133.0(12) . . ?
N1 C10 C9 108.73(19) . . ?
N1 C10 C11 120.31(19) . . ?
C9 C10 C11 130.9(2) . . ?
O1 C11 C10 108.05(16) . . ?
O1 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O1 C12 C13 115.91(18) . . ?
O1 C12 C1B 124.52(19) . . ?
C13 C12 C1B 119.56(19) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C20 C15 C14 118.03(19) . . ?
C20 C15 C16 119.3(2) . . ?
C14 C15 C16 122.7(2) . . ?
O2 C16 C17 119.8(2) . . ?
O2 C16 C15 119.7(2) . . ?
C17 C16 C15 120.5(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 N18 N3 106.75(17) . . ?
C1A C19 C5 119.8(2) . . ?
C1A C19 H19 120.1 . . ?
C5 C19 H19 120.1 . . ?
C19 C1A C1 120.7(2) . . ?
C19 C1A H1A 119.7 . . ?
C1 C1A H1A 119.7 . . ?
C20 C1B C12 119.5(2) . . ?
C20 C1B H1B 120.3 . . ?
C12 C1B H1B 120.3 . . ?
C1B C20 C15 122.0(2) . . ?
C1B C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?

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
N2 C4 C5 C19 -47(10) . . . . ?
N2 C4 C5 C6 132(9) . . . . ?
C19 C5 C6 C7 1.7(3) . . . . ?
C4 C5 C6 C7 -177.1(2) . . . . ?
C5 C6 C7 C1 -0.7(3) . . . . ?
C1A C1 C7 C6 -0.4(3) . . . . ?
C8 C1 C7 C6 175.88(19) . . . . ?
N18 N3 C8 C1 83.6(2) . . . . ?
C9 N3 C8 C1 -91.3(3) . . . . ?
C1A C1 C8 N3 89.2(2) . . . . ?
C7 C1 C8 N3 -87.1(2) . . . . ?
N18 N3 C9 C10 0.2(2) . . . . ?
C8 N3 C9 C10 175.36(19) . . . . ?
N18 N1 C10 C9 0.0(3) . . . . ?
N18 N1 C10 C11 -178.2(2) . . . . ?
N3 C9 C10 N1 -0.1(2) . . . . ?
N3 C9 C10 C11 177.8(2) . . . . ?
C12 O1 C11 C10 -178.46(16) . . . . ?
N1 C10 C11 O1 -150.81(19) . . . . ?
C9 C10 C11 O1 31.5(3) . . . . ?
C11 O1 C12 C13 178.38(18) . . . . ?
C11 O1 C12 C1B -2.6(3) . . . . ?
O1 C12 C13 C14 179.94(18) . . . . ?
C1B C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C20 0.5(3) . . . . ?
C13 C14 C15 C16 179.06(19) . . . . ?
C20 C15 C16 O2 -5.6(3) . . . . ?
C14 C15 C16 O2 175.8(2) . . . . ?
C20 C15 C16 C17 171.7(2) . . . . ?
C14 C15 C16 C17 -6.8(3) . . . . ?
C10 N1 N18 N3 0.1(3) . . . . ?
C9 N3 N18 N1 -0.2(2) . . . . ?
C8 N3 N18 N1 -175.87(18) . . . . ?
C6 C5 C19 C1A -1.4(3) . . . . ?
C4 C5 C19 C1A 177.3(2) . . . . ?
C5 C19 C1A C1 0.3(3) . . . . ?
C7 C1 C1A C19 0.7(3) . . . . ?
C8 C1 C1A C19 -175.7(2) . . . . ?
O1 C12 C1B C20 -179.12(19) . . . . ?
C13 C12 C1B C20 -0.1(3) . . . . ?
C12 C1B C20 C15 -0.5(3) . . . . ?
C14 C15 C20 C1B 0.3(3) . . . . ?
C16 C15 C20 C1B -178.36(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.041

_database_code_depnum_ccdc_archive 'CCDC 966496'
