# 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_8829
_database_code_depnum_ccdc_archive 'CCDC 1442033'
_audit_update_record             
;
2015-12-11 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2014-06-27
_audit_block_code                FNG=PB-101-03
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_compound_source        acetonitrile
_chemical_formula_moiety         'C22 H11 F10 N5 O2'
_chemical_formula_sum            'C22 H11 F10 N5 O2'
_chemical_formula_weight         567.36

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'
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'
F F 0.0171 0.0103 '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                   9.1588(9)
_cell_length_b                   10.6738(11)
_cell_length_c                   11.2243(11)
_cell_angle_alpha                96.254(2)
_cell_angle_beta                 90.635(2)
_cell_angle_gamma                93.181(2)
_cell_volume                     1088.91(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.5019
_cell_measurement_theta_max      32.4369

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0600
0.00 0.00 1.00 0.0600
1.00 0.00 0.00 0.0400
-1.00 0.00 0.00 0.0400
0.00 1.00 0.00 0.1600
0.00 -1.00 0.00 0.1600

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_correction_T_min  0.95292
_exptl_absorpt_correction_T_max  0.98771

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            34480
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         32.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7576
_reflns_number_gt                6636
_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       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_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)+(0.0469P)²+0.4439P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7576
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.85100(9) 1.51129(8) 1.39940(8) 0.01208(15) Uani 1 1 d . . . . .
C2 C 0.79466(10) 1.55755(9) 1.50854(8) 0.01339(15) Uani 1 1 d . . . . .
C3 C 0.84540(10) 1.67398(9) 1.56514(8) 0.01346(15) Uani 1 1 d . . . . .
C4 C 0.95306(10) 1.74303(9) 1.51077(8) 0.01343(15) Uani 1 1 d . . . . .
C5 C 1.00694(9) 1.69621(8) 1.40118(8) 0.01235(15) Uani 1 1 d . . . . .
C6 C 0.95854(9) 1.57942(8) 1.34243(7) 0.01098(14) Uani 1 1 d . . . . .
N7 N 1.02644(8) 1.52932(8) 1.23742(7) 0.01269(14) Uani 1 1 d . . . . .
H7 H 1.0905(15) 1.5871(13) 1.2116(12) 0.015 Uiso 1 1 d . U . . .
N8 N 0.93183(8) 1.47703(7) 1.14329(7) 0.01204(13) Uani 1 1 d D . . . .
H8 H 0.9307(15) 1.3966(11) 1.1275(12) 0.014 Uiso 1 1 d D U . . .
C9 C 0.84236(9) 1.55211(8) 1.08990(8) 0.01110(14) Uani 1 1 d . . . . .
C10 C 0.74101(9) 1.48863(8) 0.99344(7) 0.01061(14) Uani 1 1 d . . . . .
C11 C 0.68480(10) 1.56478(8) 0.91169(8) 0.01239(15) Uani 1 1 d . . . . .
H11 H 0.7172 1.6512 0.9155 0.015 Uiso 1 1 calc R U . . .
C12 C 0.58194(10) 1.51436(9) 0.82522(8) 0.01326(15) Uani 1 1 d . . . . .
H12 H 0.5461 1.5657 0.7686 0.016 Uiso 1 1 calc R U . . .
C13 C 0.53133(10) 1.38859(9) 0.82154(8) 0.01253(15) Uani 1 1 d . . . . .
H13 H 0.4584 1.3549 0.7642 0.015 Uiso 1 1 calc R U . . .
C14 C 0.58785(9) 1.31176(8) 0.90230(8) 0.01071(14) Uani 1 1 d . . . . .
C15 C 0.69537(9) 1.36102(8) 0.98671(8) 0.01104(14) Uani 1 1 d . . . . .
H15 H 0.7370 1.3080 1.0391 0.013 Uiso 1 1 calc R U . . .
C16 C 0.53408(9) 1.17670(8) 0.90057(7) 0.01082(14) Uani 1 1 d . . . . .
N17 N 0.38825(8) 1.15538(7) 0.87942(7) 0.01276(14) Uani 1 1 d . . . . .
H17 H 0.3313(16) 1.2145(13) 0.8813(12) 0.015 Uiso 1 1 d . U . . .
N18 N 0.32562(8) 1.03074(7) 0.86293(7) 0.01192(13) Uani 1 1 d D . . . .
H18 H 0.3566(15) 0.9896(12) 0.9196(11) 0.014 Uiso 1 1 d D U . . .
C19 C 0.34984(9) 0.97094(8) 0.74689(8) 0.01119(14) Uani 1 1 d . . . . .
C20 C 0.30321(9) 1.02409(8) 0.64561(8) 0.01293(15) Uani 1 1 d . . . . .
C21 C 0.32307(10) 0.96768(9) 0.53039(8) 0.01395(16) Uani 1 1 d . . . . .
C22 C 0.38897(10) 0.85363(9) 0.51280(8) 0.01396(16) Uani 1 1 d . . . . .
C23 C 0.43393(10) 0.79746(8) 0.61145(8) 0.01335(15) Uani 1 1 d . . . . .
C24 C 0.41527(9) 0.85608(8) 0.72608(8) 0.01208(15) Uani 1 1 d . . . . .
F25 F 0.80350(7) 1.39540(5) 1.35014(5) 0.01721(12) Uani 1 1 d . . . . .
F26 F 0.69569(7) 1.48637(6) 1.56163(5) 0.01940(12) Uani 1 1 d . . . . .
F27 F 0.79276(7) 1.71894(6) 1.67080(5) 0.01915(12) Uani 1 1 d . . . . .
F28 F 1.00318(7) 1.85636(6) 1.56274(6) 0.02009(12) Uani 1 1 d . . . . .
F29 F 1.10928(6) 1.76638(6) 1.34924(6) 0.01790(12) Uani 1 1 d . . . . .
O30 O 0.84438(7) 1.66684(6) 1.11990(6) 0.01528(13) Uani 1 1 d . . . . .
O31 O 0.61520(7) 1.09168(6) 0.91683(6) 0.01394(12) Uani 1 1 d . . . . .
F32 F 0.23663(7) 1.13367(6) 0.65924(6) 0.01849(12) Uani 1 1 d . . . . .
F33 F 0.27899(7) 1.02347(6) 0.43596(5) 0.02030(13) Uani 1 1 d . . . . .
F34 F 0.41231(7) 0.79963(6) 0.40190(5) 0.01987(12) Uani 1 1 d . . . . .
F35 F 0.49911(7) 0.68780(6) 0.59482(6) 0.01836(12) Uani 1 1 d . . . . .
F36 F 0.46345(7) 0.80022(6) 0.81968(5) 0.01758(12) Uani 1 1 d . . . . .
N41 N 0.03687(11) 0.79870(9) 0.87434(9) 0.02498(19) Uani 1 1 d . . . . .
C42 C -0.00286(11) 0.89413(10) 0.85455(9) 0.01746(17) Uani 1 1 d . . . . .
C43 C -0.05406(11) 1.01546(10) 0.82860(10) 0.01989(18) Uani 1 1 d . . . . .
H43A H 0.0188 1.0829 0.8576 0.030 Uiso 1 1 calc R U . . .
H43B H -0.1469 1.0302 0.8689 0.030 Uiso 1 1 calc R U . . .
H43C H -0.0684 1.0148 0.7419 0.030 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 F25 1.3457(10) . ?
C1 C2 1.3861(12) . ?
C1 C6 1.3942(12) . ?
C2 F26 1.3372(10) . ?
C2 C3 1.3862(13) . ?
C3 F27 1.3355(10) . ?
C3 C4 1.3851(13) . ?
C4 F28 1.3390(10) . ?
C4 C5 1.3832(12) . ?
C5 F29 1.3450(10) . ?
C5 C6 1.3922(12) . ?
C6 N7 1.4063(11) . ?
N7 N8 1.4058(11) . ?
N8 C9 1.3563(11) . ?
C9 O30 1.2332(11) . ?
C9 C10 1.4970(12) . ?
C10 C15 1.3962(12) . ?
C10 C11 1.4022(12) . ?
C11 C12 1.3888(13) . ?
C12 C13 1.3918(13) . ?
C13 C14 1.4003(12) . ?
C14 C15 1.3991(12) . ?
C14 C16 1.4953(12) . ?
C16 O31 1.2316(11) . ?
C16 N17 1.3563(11) . ?
N17 N18 1.4116(11) . ?
N18 C19 1.4121(11) . ?
C19 C24 1.3925(12) . ?
C19 C20 1.3976(12) . ?
C20 F32 1.3437(10) . ?
C20 C21 1.3841(13) . ?
C21 F33 1.3400(10) . ?
C21 C22 1.3845(13) . ?
C22 F34 1.3382(10) . ?
C22 C23 1.3846(13) . ?
C23 F35 1.3393(10) . ?
C23 C24 1.3847(12) . ?
C24 F36 1.3452(10) . ?
N41 C42 1.1436(14) . ?
C42 C43 1.4590(14) . ?

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
F25 C1 C2 118.48(8) . . ?
F25 C1 C6 119.67(8) . . ?
C2 C1 C6 121.80(8) . . ?
F26 C2 C1 119.43(8) . . ?
F26 C2 C3 120.10(8) . . ?
C1 C2 C3 120.40(8) . . ?
F27 C3 C4 120.24(8) . . ?
F27 C3 C2 120.88(8) . . ?
C4 C3 C2 118.88(8) . . ?
F28 C4 C5 119.75(8) . . ?
F28 C4 C3 120.22(8) . . ?
C5 C4 C3 120.01(8) . . ?
F29 C5 C4 118.77(8) . . ?
F29 C5 C6 118.83(8) . . ?
C4 C5 C6 122.40(8) . . ?
C5 C6 C1 116.50(8) . . ?
C5 C6 N7 120.66(8) . . ?
C1 C6 N7 122.55(8) . . ?
N8 N7 C6 115.83(7) . . ?
C9 N8 N7 119.87(8) . . ?
O30 C9 N8 121.46(8) . . ?
O30 C9 C10 121.88(8) . . ?
N8 C9 C10 116.66(8) . . ?
C15 C10 C11 119.93(8) . . ?
C15 C10 C9 122.89(8) . . ?
C11 C10 C9 117.08(8) . . ?
C12 C11 C10 120.29(8) . . ?
C11 C12 C13 119.96(8) . . ?
C12 C13 C14 120.01(8) . . ?
C15 C14 C13 120.17(8) . . ?
C15 C14 C16 118.96(7) . . ?
C13 C14 C16 120.87(8) . . ?
C10 C15 C14 119.53(8) . . ?
O31 C16 N17 122.65(8) . . ?
O31 C16 C14 122.94(8) . . ?
N17 C16 C14 114.41(7) . . ?
C16 N17 N18 120.23(7) . . ?
N17 N18 C19 112.09(7) . . ?
C24 C19 C20 116.38(8) . . ?
C24 C19 N18 123.15(8) . . ?
C20 C19 N18 120.44(8) . . ?
F32 C20 C21 118.22(8) . . ?
F32 C20 C19 119.52(8) . . ?
C21 C20 C19 122.26(8) . . ?
F33 C21 C20 120.10(8) . . ?
F33 C21 C22 120.01(8) . . ?
C20 C21 C22 119.89(8) . . ?
F34 C22 C21 120.54(8) . . ?
F34 C22 C23 120.24(8) . . ?
C21 C22 C23 119.20(8) . . ?
F35 C23 C22 119.40(8) . . ?
F35 C23 C24 120.40(8) . . ?
C22 C23 C24 120.18(8) . . ?
F36 C24 C23 118.54(8) . . ?
F36 C24 C19 119.38(8) . . ?
C23 C24 C19 122.07(8) . . ?
N41 C42 C43 179.62(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N8 H8 N41 0.857(11) 2.120(11) 2.9582(13) 165.9(13) 2_677
N17 H17 O30 0.839(14) 2.104(14) 2.9303(10) 168.5(13) 2_687
N18 H18 O31 0.865(11) 2.134(11) 2.9773(10) 164.9(13) 2_677

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-2



