# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_13
_database_code_depnum_ccdc_archive 'CCDC 1885848'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz, Institut of Organic Chemistry
Germany
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-4-(4-(4-fluorophenyl)-2-(phenyldiazenyl)thiazol-5-yl)pyridin-2-amine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 F N5 S'
_chemical_formula_sum            'C20 H14 F N5 S'
_chemical_formula_weight         375.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.0319(6)
_cell_length_b                   8.6937(6)
_cell_length_c                   20.5271(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.512(4)
_cell_angle_gamma                90
_cell_volume                     1781.98(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    14741
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      67.95

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.827
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8320
_exptl_absorpt_correction_T_max  0.9637
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0100
0 0 -1 0.0100
1 0 0 0.0190
-1 0 0 0.0190
0 -1 0 0.0825
0 1 0 0.0825

_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'Incoatec microSource Cu'
_diffrn_radiation_monochromator  'X-ray mirror'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 780 frames, detector distance = 40 mm
;
_diffrn_reflns_number            12766
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.328
_diffrn_reflns_theta_max         67.637
_diffrn_reflns_theta_full        67.637
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3179
_reflns_number_gt                2270
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SHELXT-20014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0547P)²] 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         3179
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
F1 F 1.09081(14) 0.9228(2) 0.41646(8) 0.0686(5) Uani 1 1 d . . . . .
C2 C 0.9637(2) 0.8815(3) 0.42743(12) 0.0430(6) Uani 1 1 d . . . . .
C3 C 0.8591(3) 0.9332(3) 0.38501(12) 0.0491(7) Uani 1 1 d . . . . .
H3 H 0.8747 0.9992 0.3496 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7305(2) 0.8874(3) 0.39481(10) 0.0384(5) Uani 1 1 d . . . . .
H4 H 0.6571 0.9205 0.3655 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7082(2) 0.7927(2) 0.44748(9) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.57062(19) 0.7395(2) 0.45601(9) 0.0222(4) Uani 1 1 d . . . . .
N7 N 0.49612(16) 0.67843(19) 0.40198(7) 0.0245(4) Uani 1 1 d . . . . .
C8 C 0.3788(2) 0.6340(2) 0.41709(9) 0.0242(4) Uani 1 1 d . . . . .
N9 N 0.28736(17) 0.56356(19) 0.37010(8) 0.0281(4) Uani 1 1 d . . . . .
N10 N 0.17715(17) 0.5340(2) 0.39263(8) 0.0287(4) Uani 1 1 d . . . . .
C11 C 0.0844(2) 0.4498(2) 0.34929(9) 0.0277(5) Uani 1 1 d . . . . .
C12 C 0.1214(2) 0.3630(3) 0.29719(11) 0.0404(6) Uani 1 1 d . . . . .
H12 H 0.2119 0.3619 0.2871 0.049 Uiso 1 1 calc R U . . .
C13 C 0.0253(3) 0.2784(3) 0.26010(12) 0.0489(6) Uani 1 1 d . . . . .
H13 H 0.0505 0.2166 0.2251 0.059 Uiso 1 1 calc R U . . .
C14 C -0.1066(3) 0.2831(3) 0.27337(11) 0.0454(6) Uani 1 1 d . . . . .
H14 H -0.1724 0.2266 0.2470 0.054 Uiso 1 1 calc R U . . .
C15 C -0.1429(3) 0.3698(3) 0.32503(13) 0.0522(7) Uani 1 1 d . . . . .
H15 H -0.2340 0.3735 0.3341 0.063 Uiso 1 1 calc R U . . .
C16 C -0.0466(2) 0.4517(3) 0.36382(11) 0.0441(6) Uani 1 1 d . . . . .
H16 H -0.0711 0.5090 0.4003 0.053 Uiso 1 1 calc R U . . .
S17 S 0.34866(5) 0.66117(6) 0.49802(2) 0.02582(14) Uani 1 1 d . . . . .
C18 C 0.50751(19) 0.7388(2) 0.51291(9) 0.0214(4) Uani 1 1 d . . . . .
C19 C 0.55002(19) 0.8007(2) 0.57893(8) 0.0214(4) Uani 1 1 d . . . . .
C20 C 0.50506(19) 0.7319(2) 0.63386(9) 0.0235(4) Uani 1 1 d . . . . .
H20 H 0.4538 0.6399 0.6297 0.028 Uiso 1 1 calc R U . . .
C21 C 0.5362(2) 0.8000(2) 0.69583(9) 0.0254(5) Uani 1 1 d . . . . .
N22 N 0.60888(17) 0.92938(19) 0.70392(8) 0.0276(4) Uani 1 1 d . . . . .
C23 C 0.6546(2) 0.9901(2) 0.65014(9) 0.0270(4) Uani 1 1 d . . . . .
H23 H 0.7092 1.0794 0.6556 0.032 Uiso 1 1 calc R U . . .
C24 C 0.6284(2) 0.9327(2) 0.58770(9) 0.0256(4) Uani 1 1 d . . . . .
H24 H 0.6628 0.9819 0.5515 0.031 Uiso 1 1 calc R U . . .
C25 C 0.8169(2) 0.7460(3) 0.49006(10) 0.0319(5) Uani 1 1 d . . . . .
H25 H 0.8023 0.6830 0.5265 0.038 Uiso 1 1 calc R U . . .
C26 C 0.9461(2) 0.7899(3) 0.48009(12) 0.0410(6) Uani 1 1 d . . . . .
H26 H 1.0204 0.7573 0.5090 0.049 Uiso 1 1 calc R U . . .
N27 N 0.4900(2) 0.7380(3) 0.75005(9) 0.0417(5) Uani 1 1 d . . . . .
H27A H 0.459(3) 0.639(3) 0.7479(12) 0.049(5) Uiso 1 1 d . U . . .
H27B H 0.513(2) 0.783(3) 0.7884(12) 0.049(5) Uiso 1 1 d . 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
F1 C2 1.364(2) . ?
C2 C26 1.368(3) . ?
C2 C3 1.373(4) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C25 1.391(3) . ?
C5 C6 1.482(3) . ?
C6 C18 1.381(3) . ?
C6 N7 1.382(2) . ?
N7 C8 1.304(2) . ?
C8 N9 1.406(2) . ?
C8 S17 1.7330(18) . ?
N9 N10 1.265(2) . ?
N10 C11 1.426(2) . ?
C11 C16 1.376(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
S17 C18 1.730(2) . ?
C18 C19 1.482(2) . ?
C19 C20 1.389(3) . ?
C19 C24 1.393(3) . ?
C20 C21 1.410(3) . ?
C20 H20 0.9500 . ?
C21 N22 1.342(3) . ?
C21 N27 1.357(3) . ?
N22 C23 1.344(2) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N27 H27A 0.91(3) . ?
N27 H27B 0.89(3) . ?

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
F1 C2 C26 118.5(2) . . ?
F1 C2 C3 118.6(2) . . ?
C26 C2 C3 122.9(2) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C25 C5 C4 119.0(2) . . ?
C25 C5 C6 121.17(18) . . ?
C4 C5 C6 119.82(19) . . ?
C18 C6 N7 114.87(17) . . ?
C18 C6 C5 127.52(17) . . ?
N7 C6 C5 117.58(16) . . ?
C8 N7 C6 110.71(15) . . ?
N7 C8 N9 120.67(17) . . ?
N7 C8 S17 115.60(14) . . ?
N9 C8 S17 123.69(15) . . ?
N10 N9 C8 111.90(16) . . ?
N9 N10 C11 114.64(16) . . ?
C16 C11 C12 120.4(2) . . ?
C16 C11 N10 115.98(19) . . ?
C12 C11 N10 123.56(19) . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.7(2) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 S17 C8 88.86(9) . . ?
C6 C18 C19 131.05(18) . . ?
C6 C18 S17 109.96(14) . . ?
C19 C18 S17 118.84(14) . . ?
C20 C19 C24 118.21(17) . . ?
C20 C19 C18 119.90(17) . . ?
C24 C19 C18 121.78(17) . . ?
C19 C20 C21 119.37(18) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N22 C21 N27 117.08(18) . . ?
N22 C21 C20 122.26(17) . . ?
N27 C21 C20 120.64(19) . . ?
C21 N22 C23 116.88(16) . . ?
N22 C23 C24 124.93(19) . . ?
N22 C23 H23 117.5 . . ?
C24 C23 H23 117.5 . . ?
C23 C24 C19 118.28(18) . . ?
C23 C24 H24 120.9 . . ?
C19 C24 H24 120.9 . . ?
C26 C25 C5 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C5 C25 H25 119.5 . . ?
C2 C26 C25 118.1(2) . . ?
C2 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C21 N27 H27A 118.4(16) . . ?
C21 N27 H27B 118.2(17) . . ?
H27A N27 H27B 121(2) . . ?

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
F1 C2 C3 C4 177.9(2) . . . . ?
C26 C2 C3 C4 -1.8(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C25 0.3(3) . . . . ?
C3 C4 C5 C6 -177.7(2) . . . . ?
C25 C5 C6 C18 48.2(3) . . . . ?
C4 C5 C6 C18 -133.8(2) . . . . ?
C25 C5 C6 N7 -129.6(2) . . . . ?
C4 C5 C6 N7 48.4(3) . . . . ?
C18 C6 N7 C8 0.7(2) . . . . ?
C5 C6 N7 C8 178.78(17) . . . . ?
C6 N7 C8 N9 -177.92(17) . . . . ?
C6 N7 C8 S17 -0.4(2) . . . . ?
N7 C8 N9 N10 -177.33(18) . . . . ?
S17 C8 N9 N10 5.3(2) . . . . ?
C8 N9 N10 C11 -174.55(16) . . . . ?
N9 N10 C11 C16 -162.9(2) . . . . ?
N9 N10 C11 C12 20.5(3) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
N10 C11 C12 C13 176.4(2) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
C12 C13 C14 C15 -1.6(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C12 C11 C16 C15 -1.8(4) . . . . ?
N10 C11 C16 C15 -178.5(2) . . . . ?
C14 C15 C16 C11 2.0(4) . . . . ?
N7 C8 S17 C18 -0.03(16) . . . . ?
N9 C8 S17 C18 177.44(17) . . . . ?
N7 C6 C18 C19 -176.13(19) . . . . ?
C5 C6 C18 C19 6.0(4) . . . . ?
N7 C6 C18 S17 -0.7(2) . . . . ?
C5 C6 C18 S17 -178.57(16) . . . . ?
C8 S17 C18 C6 0.42(15) . . . . ?
C8 S17 C18 C19 176.46(16) . . . . ?
C6 C18 C19 C20 -151.0(2) . . . . ?
S17 C18 C19 C20 33.9(2) . . . . ?
C6 C18 C19 C24 32.8(3) . . . . ?
S17 C18 C19 C24 -142.25(17) . . . . ?
C24 C19 C20 C21 2.0(3) . . . . ?
C18 C19 C20 C21 -174.28(18) . . . . ?
C19 C20 C21 N22 -0.4(3) . . . . ?
C19 C20 C21 N27 177.9(2) . . . . ?
N27 C21 N22 C23 179.8(2) . . . . ?
C20 C21 N22 C23 -1.8(3) . . . . ?
C21 N22 C23 C24 2.5(3) . . . . ?
N22 C23 C24 C19 -0.9(3) . . . . ?
C20 C19 C24 C23 -1.4(3) . . . . ?
C18 C19 C24 C23 174.79(18) . . . . ?
C4 C5 C25 C26 -1.1(3) . . . . ?
C6 C5 C25 C26 176.82(19) . . . . ?
F1 C2 C26 C25 -178.7(2) . . . . ?
C3 C2 C26 C25 1.0(4) . . . . ?
C5 C25 C26 C2 0.5(3) . . . . ?

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
C23 H23 F1 0.95 2.60 3.104(2) 113.2 3_776
C24 H24 F1 0.95 2.63 3.093(2) 110.5 3_776
N27 H27B N7 0.89(3) 2.38(3) 3.197(2) 153(2) 4_576
N27 H27A N22 0.91(3) 2.21(3) 3.043(3) 151(2) 2_646

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.053

