# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2020

####################################################################### 
# 
# 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 1037923'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H34 F6 O6'
_chemical_formula_sum            'C29 H34 F6 O6'
_chemical_formula_weight         592.56

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'
F F 0.0171 0.0103 '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 2yc'

_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+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'

_cell_length_a                   21.3540(16)
_cell_length_b                   12.3394(10)
_cell_length_c                   10.9586(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.844(6)
_cell_angle_gamma                90
_cell_volume                     2826.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10025
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      26.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            17707
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         25.767
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2669
_reflns_number_gt                1756
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0640P)²] 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         2669
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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
C1 C 0.18713(11) 0.6781(2) 0.0575(2) 0.0218(6) Uani 1 1 d . . . . .
H1 H 0.2256 0.6591 0.0265 0.026 Uiso 1 1 calc R U . . .
C2 C 0.14026(11) 0.7329(2) -0.0429(2) 0.0203(5) Uani 1 1 d . . . . .
C3 C 0.10837(11) 0.8269(2) -0.0448(2) 0.0203(5) Uani 1 1 d . . . . .
H3 H 0.1099 0.8745 0.0214 0.024 Uiso 1 1 calc R U . . .
C4 C 0.07148(10) 0.8393(2) -0.1693(2) 0.0190(5) Uani 1 1 d . . . . .
C5 C 0.08472(10) 0.7522(2) -0.2356(2) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.06815(11) 0.7211(2) -0.3697(2) 0.0234(6) Uani 1 1 d . . . . .
H6A H 0.1073 0.7194 -0.4016 0.028 Uiso 1 1 calc R U . . .
H6B H 0.0411 0.7773 -0.4147 0.028 Uiso 1 1 calc R U . . .
C7 C 0.03421(13) 0.6126(2) -0.3985(3) 0.0304(7) Uani 1 1 d . . . . .
H7A H 0.0256 0.6002 -0.4869 0.046 Uiso 1 1 calc R U . . .
H7B H -0.0053 0.6136 -0.3697 0.046 Uiso 1 1 calc R U . . .
H7C H 0.0610 0.5556 -0.3571 0.046 Uiso 1 1 calc R U . . .
C8 C 0.02982(11) 0.9313(2) -0.2148(2) 0.0208(5) Uani 1 1 d . . . . .
C9 C 0.05260(12) 1.0437(2) -0.1819(3) 0.0309(7) Uani 1 1 d . . . . .
C10 C 0.0000 1.1200(3) -0.2500 0.0244(8) Uani 1 2 d S T P . .
C11 C 0.24799(12) 0.7092(2) 0.2569(2) 0.0278(6) Uani 1 1 d . . . . .
H11A H 0.2570 0.7620 0.3238 0.033 Uiso 1 1 calc R U . . .
H11B H 0.2877 0.6939 0.2303 0.033 Uiso 1 1 calc R U . . .
C12 C 0.22319(11) 0.6053(2) 0.3056(2) 0.0232(6) Uani 1 1 d . . . . .
C13 C 0.20336(12) 0.5309(2) 0.1940(2) 0.0257(6) Uani 1 1 d . . . . .
H13A H 0.2411 0.5087 0.1639 0.031 Uiso 1 1 calc R U . . .
H13B H 0.1835 0.4664 0.2195 0.031 Uiso 1 1 calc R U . . .
C14 C 0.27790(13) 0.5532(3) 0.3994(3) 0.0330(7) Uani 1 1 d . . . . .
H14A H 0.2903 0.6003 0.4699 0.050 Uiso 1 1 calc R U . . .
H14B H 0.3138 0.5416 0.3606 0.050 Uiso 1 1 calc R U . . .
H14C H 0.2639 0.4851 0.4266 0.050 Uiso 1 1 calc R U . . .
C15 C 0.16608(13) 0.6294(3) 0.3658(3) 0.0352(7) Uani 1 1 d . . . . .
H15A H 0.1793 0.6768 0.4358 0.053 Uiso 1 1 calc R U . . .
H15B H 0.1502 0.5629 0.3934 0.053 Uiso 1 1 calc R U . . .
H15C H 0.1329 0.6637 0.3059 0.053 Uiso 1 1 calc R U . . .
F1 F 0.10883(8) 1.06492(15) -0.2157(3) 0.0719(8) Uani 1 1 d . . . . .
F2 F 0.06352(12) 1.06178(16) -0.05763(18) 0.0699(7) Uani 1 1 d . . . . .
F3 F -0.02159(8) 1.18382(19) -0.17030(18) 0.0592(6) Uani 1 1 d . . . . .
O1 O 0.12686(7) 0.68486(14) -0.15878(15) 0.0205(4) Uani 1 1 d . . . . .
O2 O 0.20264(8) 0.75403(14) 0.15416(16) 0.0248(4) Uani 1 1 d . . . . .
O3 O 0.15919(8) 0.58351(15) 0.09465(16) 0.0248(4) Uani 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
C1 O2 1.402(3) . ?
C1 O3 1.409(3) . ?
C1 C2 1.489(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.343(4) . ?
C2 O1 1.377(3) . ?
C3 C4 1.437(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(3) . ?
C4 C8 1.465(3) . ?
C5 O1 1.378(3) . ?
C5 C6 1.489(3) . ?
C6 C7 1.525(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C8 1.347(5) 2_554 ?
C8 C9 1.490(4) . ?
C9 F2 1.352(3) . ?
C9 F1 1.353(3) . ?
C9 C10 1.536(4) . ?
C10 F3 1.327(3) . ?
C10 F3 1.327(3) 2_554 ?
C10 C9 1.536(4) 2_554 ?
C11 O2 1.437(3) . ?
C11 C12 1.524(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(4) . ?
C12 C15 1.530(4) . ?
C12 C14 1.531(4) . ?
C13 O3 1.440(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
O2 C1 O3 112.55(19) . . ?
O2 C1 C2 105.9(2) . . ?
O3 C1 C2 109.22(19) . . ?
O2 C1 H1 109.7 . . ?
O3 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C3 C2 O1 110.4(2) . . ?
C3 C2 C1 131.7(2) . . ?
O1 C2 C1 117.9(2) . . ?
C2 C3 C4 106.5(2) . . ?
C2 C3 H3 126.7 . . ?
C4 C3 H3 126.7 . . ?
C5 C4 C3 106.8(2) . . ?
C5 C4 C8 127.5(2) . . ?
C3 C4 C8 125.6(2) . . ?
C4 C5 O1 109.4(2) . . ?
C4 C5 C6 134.3(2) . . ?
O1 C5 C6 116.1(2) . . ?
C5 C6 C7 115.9(2) . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C7 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C8 C4 129.17(13) 2_554 . ?
C8 C8 C9 111.23(14) 2_554 . ?
C4 C8 C9 119.6(2) . . ?
F2 C9 F1 105.4(2) . . ?
F2 C9 C8 112.2(2) . . ?
F1 C9 C8 112.2(2) . . ?
F2 C9 C10 110.2(2) . . ?
F1 C9 C10 110.5(2) . . ?
C8 C9 C10 106.5(2) . . ?
F3 C10 F3 107.2(3) . 2_554 ?
F3 C10 C9 111.24(13) . . ?
F3 C10 C9 111.41(14) 2_554 . ?
F3 C10 C9 111.41(14) . 2_554 ?
F3 C10 C9 111.24(13) 2_554 2_554 ?
C9 C10 C9 104.4(3) . 2_554 ?
O2 C11 C12 111.8(2) . . ?
O2 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O2 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 106.6(2) . . ?
C13 C12 C15 110.5(2) . . ?
C11 C12 C15 110.6(2) . . ?
C13 C12 C14 109.6(2) . . ?
C11 C12 C14 108.4(2) . . ?
C15 C12 C14 111.0(2) . . ?
O3 C13 C12 111.6(2) . . ?
O3 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O3 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 O1 C5 106.85(19) . . ?
C1 O2 C11 110.6(2) . . ?
C1 O3 C13 109.96(18) . . ?

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
O2 C1 C2 C3 -10.0(3) . . . . ?
O3 C1 C2 C3 111.4(3) . . . . ?
O2 C1 C2 O1 166.99(18) . . . . ?
O3 C1 C2 O1 -71.6(3) . . . . ?
O1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C8 -179.1(2) . . . . ?
C3 C4 C5 O1 1.2(2) . . . . ?
C8 C4 C5 O1 179.0(2) . . . . ?
C3 C4 C5 C6 -172.8(2) . . . . ?
C8 C4 C5 C6 5.0(4) . . . . ?
C4 C5 C6 C7 -123.8(3) . . . . ?
O1 C5 C6 C7 62.5(3) . . . . ?
C5 C4 C8 C8 47.6(5) . . . 2_554 ?
C3 C4 C8 C8 -135.0(3) . . . 2_554 ?
C5 C4 C8 C9 -133.1(3) . . . . ?
C3 C4 C8 C9 44.3(3) . . . . ?
C8 C8 C9 F2 116.7(3) 2_554 . . . ?
C4 C8 C9 F2 -62.8(3) . . . . ?
C8 C8 C9 F1 -125.0(3) 2_554 . . . ?
C4 C8 C9 F1 55.6(3) . . . . ?
C8 C8 C9 C10 -4.0(3) 2_554 . . . ?
C4 C8 C9 C10 176.60(18) . . . . ?
F2 C9 C10 F3 -0.2(3) . . . . ?
F1 C9 C10 F3 -116.3(2) . . . . ?
C8 C9 C10 F3 121.6(2) . . . . ?
F2 C9 C10 F3 119.3(3) . . . 2_554 ?
F1 C9 C10 F3 3.3(3) . . . 2_554 ?
C8 C9 C10 F3 -118.8(2) . . . 2_554 ?
F2 C9 C10 C9 -120.5(2) . . . 2_554 ?
F1 C9 C10 C9 123.4(2) . . . 2_554 ?
C8 C9 C10 C9 1.35(11) . . . 2_554 ?
O2 C11 C12 C13 52.9(3) . . . . ?
O2 C11 C12 C15 -67.2(3) . . . . ?
O2 C11 C12 C14 170.9(2) . . . . ?
C11 C12 C13 O3 -53.7(3) . . . . ?
C15 C12 C13 O3 66.6(3) . . . . ?
C14 C12 C13 O3 -170.9(2) . . . . ?
C3 C2 O1 C5 -0.1(2) . . . . ?
C1 C2 O1 C5 -177.7(2) . . . . ?
C4 C5 O1 C2 -0.8(2) . . . . ?
C6 C5 O1 C2 174.52(19) . . . . ?
O3 C1 O2 C11 60.7(2) . . . . ?
C2 C1 O2 C11 179.97(18) . . . . ?
C12 C11 O2 C1 -57.0(3) . . . . ?
O2 C1 O3 C13 -61.2(2) . . . . ?
C2 C1 O3 C13 -178.6(2) . . . . ?
C12 C13 O3 C1 58.4(2) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexanes'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1037924'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 F4 N5 S2'
_chemical_formula_sum            'C29 H21 F4 N5 S2'
_chemical_formula_weight         579.63

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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                   6.3781(16)
_cell_length_b                   13.826(4)
_cell_length_c                   15.124(4)
_cell_angle_alpha                92.61(2)
_cell_angle_beta                 91.07(2)
_cell_angle_gamma                96.54(2)
_cell_volume                     1323.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19106
_cell_measurement_theta_min      1.48
_cell_measurement_theta_max      22.28

_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            14778
_diffrn_reflns_av_unetI/netI     0.1389
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.484
_diffrn_reflns_theta_max         26.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5138
_reflns_number_gt                1975
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0568P)²] 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         5138
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.846
_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
C1 C 1.0727(10) 0.8912(4) 0.4063(3) 0.0736(14) Uani 1 1 d . . . . .
C2 C 0.8592(8) 0.9117(3) 0.4194(3) 0.0684(13) Uani 1 1 d . . . . .
C3 C 0.7900(8) 0.9889(4) 0.3697(3) 0.0769(14) Uani 1 1 d . . . . .
C4 C 0.7301(8) 0.8706(3) 0.4816(3) 0.0711(13) Uani 1 1 d . . . . .
H4A H 0.5937 0.8918 0.4841 0.085 Uiso 1 1 calc R U . . .
C5 C 0.7730(8) 0.7986(3) 0.5449(3) 0.0708(13) Uani 1 1 d . . . . .
C6 C 0.6568(7) 0.7889(3) 0.6210(3) 0.0648(12) Uani 1 1 d . . . . .
H6A H 0.5341 0.8202 0.6318 0.078 Uiso 1 1 calc R U . . .
C7 C 0.7418(8) 0.7269(3) 0.6808(3) 0.0649(12) Uani 1 1 d . . . . .
C8 C 0.9093(7) 0.6840(3) 0.6464(3) 0.0635(12) Uani 1 1 d . . . . .
C9 C 1.0221(7) 0.6074(3) 0.6875(3) 0.0655(12) Uani 1 1 d . . . . .
H9A H 1.0770 0.6352 0.7468 0.079 Uiso 1 1 calc R U . . .
C18 C 0.8664(7) 0.5147(3) 0.7047(3) 0.0628(12) Uani 1 1 d . . . . .
C17 C 0.7267(7) 0.5315(3) 0.7848(3) 0.0658(12) Uani 1 1 d . . . . .
C16 C 0.7240(8) 0.4521(3) 0.8431(3) 0.0686(13) Uani 1 1 d . . . . .
H12A H 0.6259 0.4443 0.8894 0.082 Uiso 1 1 calc R U . . .
C15 C 0.8682(8) 0.3891(3) 0.8286(3) 0.0661(12) Uani 1 1 d . . . . .
C14 C 0.9020(8) 0.3174(3) 0.8904(3) 0.0698(13) Uani 1 1 d . . . . .
H14A H 0.8058 0.3131 0.9376 0.084 Uiso 1 1 calc R U . . .
C12 C 1.0494(8) 0.2545(3) 0.8925(3) 0.0710(13) Uani 1 1 d . . . . .
C13 C 1.2027(9) 0.2433(4) 0.8253(3) 0.0788(14) Uani 1 1 d . . . . .
C11 C 1.0558(8) 0.1920(4) 0.9675(3) 0.0726(13) Uani 1 1 d . . . . .
C22 C 0.6393(7) 0.6140(3) 0.8071(3) 0.0615(12) Uani 1 1 d . . . . .
C21 C 0.6502(7) 0.7072(3) 0.7685(3) 0.0631(12) Uani 1 1 d . . . . .
C25 C 0.5696(8) 0.7775(4) 0.8218(3) 0.0660(12) Uani 1 1 d . . . . .
C24 C 0.4441(8) 0.7259(4) 0.8936(3) 0.0695(13) Uani 1 1 d . . . . .
C23 C 0.5137(8) 0.6224(4) 0.8910(3) 0.0685(13) Uani 1 1 d . . . . .
C29 C 0.7715(8) 0.9305(3) 0.7773(3) 0.0788(14) Uani 1 1 d . . . . .
H23A H 0.7383 0.9392 0.7142 0.095 Uiso 1 1 calc R U . . .
H23B H 0.9011 0.8977 0.7816 0.095 Uiso 1 1 calc R U . . .
C28 C 0.7975(10) 1.0259(4) 0.8285(3) 0.0919(17) Uani 1 1 d . . . . .
H24A H 0.8629 1.0786 0.7922 0.110 Uiso 1 1 calc R U . . .
H24B H 0.8850 1.0230 0.8828 0.110 Uiso 1 1 calc R U . . .
C27 C 0.5751(11) 1.0410(4) 0.8504(3) 0.0949(18) Uani 1 1 d . . . . .
H25A H 0.5007 1.0643 0.7989 0.114 Uiso 1 1 calc R U . . .
H25B H 0.5720 1.0888 0.9010 0.114 Uiso 1 1 calc R U . . .
C26 C 0.4751(9) 0.9402(3) 0.8742(3) 0.0860(16) Uani 1 1 d . . . . .
H26A H 0.4942 0.9303 0.9382 0.103 Uiso 1 1 calc R U . . .
H26B H 0.3225 0.9307 0.8586 0.103 Uiso 1 1 calc R U . . .
C10 C 1.2158(7) 0.5840(3) 0.6343(3) 0.0739(13) Uani 1 1 d . . . . .
H27C H 1.3001 0.5437 0.6690 0.089 Uiso 1 1 calc R U . . .
H27B H 1.3019 0.6448 0.6215 0.089 Uiso 1 1 calc R U . . .
H27A H 1.1682 0.5486 0.5786 0.089 Uiso 1 1 calc R U . . .
C19 C 0.7359(7) 0.4796(3) 0.6203(3) 0.0668(12) Uani 1 1 d . . . . .
H28B H 0.6552 0.5329 0.6025 0.080 Uiso 1 1 calc R U . . .
H28A H 0.8348 0.4678 0.5724 0.080 Uiso 1 1 calc R U . . .
C20 C 0.5815(8) 0.3878(3) 0.6274(3) 0.0758(13) Uani 1 1 d . . . . .
H29C H 0.5037 0.3731 0.5710 0.091 Uiso 1 1 calc R U . . .
H29B H 0.4820 0.3981 0.6745 0.091 Uiso 1 1 calc R U . . .
H29A H 0.6597 0.3330 0.6411 0.091 Uiso 1 1 calc R U . . .
F4 F 0.4709(4) 0.76887(18) 0.97555(15) 0.0761(7) Uani 1 1 d . . . . .
F3 F 0.2322(5) 0.72099(19) 0.87552(16) 0.0791(8) Uani 1 1 d . . . . .
F1 F 0.3451(5) 0.55416(19) 0.89551(16) 0.0789(7) Uani 1 1 d . . . . .
F2 F 0.6342(4) 0.61444(18) 0.96542(15) 0.0798(8) Uani 1 1 d . . . . .
N2 N 1.2441(8) 0.8781(3) 0.3962(3) 0.0905(14) Uani 1 1 d . . . . .
N1 N 0.7389(7) 1.0540(3) 0.3328(3) 0.0864(13) Uani 1 1 d . . . . .
N4 N 1.3220(8) 0.2293(3) 0.7729(3) 0.1053(16) Uani 1 1 d . . . . .
N3 N 1.0605(7) 0.1427(3) 1.0260(3) 0.0848(13) Uani 1 1 d . . . . .
N5 N 0.5920(6) 0.8739(3) 0.8201(2) 0.0706(11) Uani 1 1 d . . . . .
S1 S 0.9736(2) 0.72617(9) 0.54301(7) 0.0704(4) Uani 1 1 d . . . . .
S2 S 1.0234(2) 0.41523(9) 0.73605(7) 0.0715(4) Uani 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
C1 N2 1.140(6) . ?
C1 C2 1.437(7) . ?
C2 C4 1.362(6) . ?
C2 C3 1.438(7) . ?
C3 N1 1.155(5) . ?
C4 C5 1.457(6) . ?
C5 C6 1.384(5) . ?
C5 S1 1.712(5) . ?
C6 C7 1.416(6) . ?
C7 C8 1.379(6) . ?
C7 C21 1.483(6) . ?
C8 C9 1.496(6) . ?
C8 S1 1.734(4) . ?
C9 C10 1.544(6) . ?
C9 C18 1.565(6) . ?
C18 C19 1.539(6) . ?
C18 C17 1.541(6) . ?
C18 S2 1.864(4) . ?
C17 C22 1.358(6) . ?
C17 C16 1.438(6) . ?
C16 C15 1.351(6) . ?
C15 C14 1.425(6) . ?
C15 S2 1.756(4) . ?
C14 C12 1.352(6) . ?
C12 C13 1.439(7) . ?
C12 C11 1.459(6) . ?
C13 N4 1.135(5) . ?
C11 N3 1.143(5) . ?
C22 C21 1.433(6) . ?
C22 C23 1.521(6) . ?
C21 C25 1.384(6) . ?
C25 N5 1.325(5) . ?
C25 C24 1.517(6) . ?
C24 F4 1.349(5) . ?
C24 F3 1.367(5) . ?
C24 C23 1.545(6) . ?
C23 F1 1.352(5) . ?
C23 F2 1.367(5) . ?
C29 N5 1.487(6) . ?
C29 C28 1.489(6) . ?
C28 C27 1.498(7) . ?
C27 C26 1.527(7) . ?
C26 N5 1.476(5) . ?
C19 C20 1.525(6) . ?

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
N2 C1 C2 177.8(6) . . ?
C4 C2 C1 124.4(4) . . ?
C4 C2 C3 118.9(4) . . ?
C1 C2 C3 116.3(4) . . ?
N1 C3 C2 176.8(6) . . ?
C2 C4 C5 128.7(4) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 S1 112.0(3) . . ?
C4 C5 S1 127.4(3) . . ?
C5 C6 C7 112.2(4) . . ?
C8 C7 C6 112.6(4) . . ?
C8 C7 C21 124.6(4) . . ?
C6 C7 C21 122.7(4) . . ?
C7 C8 C9 126.9(4) . . ?
C7 C8 S1 111.3(3) . . ?
C9 C8 S1 121.8(3) . . ?
C8 C9 C10 112.2(3) . . ?
C8 C9 C18 111.2(4) . . ?
C10 C9 C18 112.9(4) . . ?
C19 C18 C17 112.5(4) . . ?
C19 C18 C9 110.7(3) . . ?
C17 C18 C9 111.7(3) . . ?
C19 C18 S2 108.0(3) . . ?
C17 C18 S2 105.1(3) . . ?
C9 C18 S2 108.6(3) . . ?
C22 C17 C16 121.9(4) . . ?
C22 C17 C18 126.8(4) . . ?
C16 C17 C18 110.7(4) . . ?
C15 C16 C17 116.5(4) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 S2 113.3(3) . . ?
C14 C15 S2 125.2(4) . . ?
C12 C14 C15 130.2(4) . . ?
C14 C12 C13 124.8(4) . . ?
C14 C12 C11 118.8(4) . . ?
C13 C12 C11 116.4(4) . . ?
N4 C13 C12 176.3(5) . . ?
N3 C11 C12 179.8(6) . . ?
C17 C22 C21 132.4(4) . . ?
C17 C22 C23 121.2(4) . . ?
C21 C22 C23 106.3(4) . . ?
C25 C21 C22 113.4(4) . . ?
C25 C21 C7 123.2(4) . . ?
C22 C21 C7 123.4(4) . . ?
N5 C25 C21 131.4(4) . . ?
N5 C25 C24 120.8(4) . . ?
C21 C25 C24 107.8(4) . . ?
F4 C24 F3 104.9(4) . . ?
F4 C24 C25 115.5(4) . . ?
F3 C24 C25 110.8(4) . . ?
F4 C24 C23 111.2(4) . . ?
F3 C24 C23 110.1(4) . . ?
C25 C24 C23 104.5(4) . . ?
F1 C23 F2 105.9(4) . . ?
F1 C23 C22 114.4(4) . . ?
F2 C23 C22 112.0(4) . . ?
F1 C23 C24 110.9(4) . . ?
F2 C23 C24 107.9(4) . . ?
C22 C23 C24 105.7(4) . . ?
N5 C29 C28 103.9(4) . . ?
C29 C28 C27 102.9(5) . . ?
C28 C27 C26 104.0(4) . . ?
N5 C26 C27 103.0(4) . . ?
C20 C19 C18 116.1(4) . . ?
C25 N5 C26 125.7(4) . . ?
C25 N5 C29 123.2(4) . . ?
C26 N5 C29 109.9(4) . . ?
C5 S1 C8 91.6(2) . . ?
C15 S2 C18 92.3(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
C1 C2 C4 C5 -1.5(8) . . . . ?
C3 C2 C4 C5 -173.9(5) . . . . ?
C2 C4 C5 C6 158.2(5) . . . . ?
C2 C4 C5 S1 -15.6(8) . . . . ?
C4 C5 C6 C7 -170.6(4) . . . . ?
S1 C5 C6 C7 4.2(5) . . . . ?
C5 C6 C7 C8 -5.3(6) . . . . ?
C5 C6 C7 C21 178.0(4) . . . . ?
C6 C7 C8 C9 -173.5(4) . . . . ?
C21 C7 C8 C9 3.2(8) . . . . ?
C6 C7 C8 S1 4.0(5) . . . . ?
C21 C7 C8 S1 -179.3(4) . . . . ?
C7 C8 C9 C10 -174.4(4) . . . . ?
S1 C8 C9 C10 8.4(6) . . . . ?
C7 C8 C9 C18 58.0(6) . . . . ?
S1 C8 C9 C18 -119.2(4) . . . . ?
C8 C9 C18 C19 51.4(4) . . . . ?
C10 C9 C18 C19 -75.8(4) . . . . ?
C8 C9 C18 C17 -74.8(4) . . . . ?
C10 C9 C18 C17 158.0(4) . . . . ?
C8 C9 C18 S2 169.8(3) . . . . ?
C10 C9 C18 S2 42.5(4) . . . . ?
C19 C18 C17 C22 -86.2(5) . . . . ?
C9 C18 C17 C22 38.9(6) . . . . ?
S2 C18 C17 C22 156.6(4) . . . . ?
C19 C18 C17 C16 102.6(4) . . . . ?
C9 C18 C17 C16 -132.3(4) . . . . ?
S2 C18 C17 C16 -14.6(4) . . . . ?
C22 C17 C16 C15 -159.6(5) . . . . ?
C18 C17 C16 C15 12.1(6) . . . . ?
C17 C16 C15 C14 169.9(4) . . . . ?
C17 C16 C15 S2 -2.9(6) . . . . ?
C16 C15 C14 C12 -173.2(5) . . . . ?
S2 C15 C14 C12 -1.3(8) . . . . ?
C15 C14 C12 C13 -4.1(9) . . . . ?
C15 C14 C12 C11 176.3(5) . . . . ?
C16 C17 C22 C21 168.5(5) . . . . ?
C18 C17 C22 C21 -1.8(8) . . . . ?
C16 C17 C22 C23 -6.5(7) . . . . ?
C18 C17 C22 C23 -176.8(4) . . . . ?
C17 C22 C21 C25 -168.4(5) . . . . ?
C23 C22 C21 C25 7.1(5) . . . . ?
C17 C22 C21 C7 10.7(8) . . . . ?
C23 C22 C21 C7 -173.8(4) . . . . ?
C8 C7 C21 C25 145.3(5) . . . . ?
C6 C7 C21 C25 -38.3(7) . . . . ?
C8 C7 C21 C22 -33.7(7) . . . . ?
C6 C7 C21 C22 142.7(5) . . . . ?
C22 C21 C25 N5 162.9(5) . . . . ?
C7 C21 C25 N5 -16.2(8) . . . . ?
C22 C21 C25 C24 -14.5(5) . . . . ?
C7 C21 C25 C24 166.4(4) . . . . ?
N5 C25 C24 F4 -39.9(6) . . . . ?
C21 C25 C24 F4 137.9(4) . . . . ?
N5 C25 C24 F3 79.1(5) . . . . ?
C21 C25 C24 F3 -103.1(4) . . . . ?
N5 C25 C24 C23 -162.4(4) . . . . ?
C21 C25 C24 C23 15.4(5) . . . . ?
C17 C22 C23 F1 -58.5(6) . . . . ?
C21 C22 C23 F1 125.4(4) . . . . ?
C17 C22 C23 F2 62.0(6) . . . . ?
C21 C22 C23 F2 -114.1(4) . . . . ?
C17 C22 C23 C24 179.2(4) . . . . ?
C21 C22 C23 C24 3.1(5) . . . . ?
F4 C24 C23 F1 99.3(4) . . . . ?
F3 C24 C23 F1 -16.5(5) . . . . ?
C25 C24 C23 F1 -135.5(4) . . . . ?
F4 C24 C23 F2 -16.3(5) . . . . ?
F3 C24 C23 F2 -132.0(4) . . . . ?
C25 C24 C23 F2 109.0(4) . . . . ?
F4 C24 C23 C22 -136.3(4) . . . . ?
F3 C24 C23 C22 108.0(4) . . . . ?
C25 C24 C23 C22 -11.0(5) . . . . ?
N5 C29 C28 C27 -35.1(5) . . . . ?
C29 C28 C27 C26 40.7(5) . . . . ?
C28 C27 C26 N5 -29.9(5) . . . . ?
C17 C18 C19 C20 -55.9(5) . . . . ?
C9 C18 C19 C20 178.4(4) . . . . ?
S2 C18 C19 C20 59.6(4) . . . . ?
C21 C25 N5 C26 171.8(5) . . . . ?
C24 C25 N5 C26 -11.0(7) . . . . ?
C21 C25 N5 C29 -21.9(7) . . . . ?
C24 C25 N5 C29 155.2(4) . . . . ?
C27 C26 N5 C25 175.9(4) . . . . ?
C27 C26 N5 C29 8.1(5) . . . . ?
C28 C29 N5 C25 -151.4(4) . . . . ?
C28 C29 N5 C26 16.8(5) . . . . ?
C6 C5 S1 C8 -1.6(4) . . . . ?
C4 C5 S1 C8 172.7(5) . . . . ?
C7 C8 S1 C5 -1.4(4) . . . . ?
C9 C8 S1 C5 176.2(4) . . . . ?
C16 C15 S2 C18 -5.5(4) . . . . ?
C14 C15 S2 C18 -178.0(4) . . . . ?
C19 C18 S2 C15 -109.0(3) . . . . ?
C17 C18 S2 C15 11.3(3) . . . . ?
C9 C18 S2 C15 131.0(3) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CD2Cl2'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 894167'
_audit_update_record             
;
2012-07-29 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
#TrackingRef '12920_web_deposit_cif_file_0_thomashuhn_1343575040.ds08_pub.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H10 F6 N4 O2'
_chemical_formula_sum            'C23 H10 F6 N4 O2'
_chemical_formula_weight         488.35

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   21.890(4)
_cell_length_b                   9.2771(15)
_cell_length_c                   10.6726(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.344(12)
_cell_angle_gamma                90.00
_cell_volume                     2138.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8437
_cell_measurement_theta_min      1.81
_cell_measurement_theta_max      27.05

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14031
_diffrn_reflns_av_R_equivalents  0.2274
_diffrn_reflns_av_sigmaI/netI    0.2457
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.82
_reflns_number_total             2275
_reflns_number_gt                1357
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0563P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
F1A F 0.0952(2) 1.0897(4) 0.3393(6) 0.0550(17) Uani 0.494(8) 1 d P A 1
F2A F 0.0468(3) 1.0723(5) 0.0701(5) 0.0489(14) Uani 0.494(8) 1 d P A 1
F3A F 0.0325(2) 1.2008(7) 0.3674(4) 0.0575(15) Uani 0.494(8) 1 d P A 1
F1B F 0.11123(17) 1.0820(4) 0.2484(7) 0.0576(19) Uani 0.506(8) 1 d P A 2
F2B F 0.0731(3) 1.0907(5) 0.1341(7) 0.0530(14) Uani 0.506(8) 1 d P A 2
F3B F 0.0072(3) 1.2724(5) 0.3219(5) 0.0615(16) Uani 0.506(8) 1 d P . 2
O1 O 0.12565(7) 0.58285(17) 0.26568(16) 0.0325(4) Uani 1 1 d . . .
N1 N 0.20696(11) 0.2981(3) 0.3212(2) 0.0489(6) Uani 1 1 d . . .
N2 N 0.30888(12) 0.3788(3) 0.0094(3) 0.0692(9) Uani 1 1 d . . .
C1 C 0.27071(13) 0.4157(3) 0.0637(3) 0.0477(7) Uani 1 1 d . . .
C2 C 0.22309(11) 0.4609(3) 0.1335(3) 0.0357(6) Uani 1 1 d . . .
C3 C 0.19142(11) 0.5836(3) 0.1028(3) 0.0368(6) Uani 1 1 d . . .
H3 H 0.2015 0.6327 0.0329 0.044 Uiso 1 1 calc R . .
C4 C 0.14447(11) 0.6494(3) 0.1625(2) 0.0321(6) Uani 1 1 d . . .
C5 C 0.11300(11) 0.7736(3) 0.1364(2) 0.0353(6) Uani 1 1 d . . .
H5 H 0.1177 0.8387 0.0724 0.042 Uiso 1 1 calc R . .
C6 C 0.07113(10) 0.7866(2) 0.2252(2) 0.0289(5) Uani 1 1 d . . .
C7 C 0.02908(11) 0.9064(2) 0.2368(2) 0.0320(6) Uani 1 1 d . . .
C8 C 0.05051(14) 1.0574(3) 0.2197(4) 0.0581(10) Uani 1 1 d . . .
C9 C 0.0000 1.1550(4) 0.2500 0.0506(11) Uani 1 2 d S . .
C10 C 0.08117(10) 0.6686(3) 0.3030(2) 0.0298(6) Uani 1 1 d . . .
C11 C 0.05722(12) 0.6215(3) 0.4176(3) 0.0410(7) Uani 1 1 d . . .
H11A H 0.0317 0.5377 0.3981 0.062 Uiso 1 1 calc R . .
H11B H 0.0331 0.6975 0.4462 0.062 Uiso 1 1 calc R . .
H11C H 0.0912 0.5984 0.4833 0.062 Uiso 1 1 calc R . .
C12 C 0.21389(11) 0.3708(3) 0.2376(3) 0.0369(6) Uani 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
F1A C8 1.507(5) . ?
F2A C8 1.592(7) . ?
F3A C9 1.403(4) . ?
F1B C8 1.334(4) . ?
F1B F2B 1.363(12) . ?
F2B C8 1.150(6) . ?
F3B C9 1.327(5) . ?
F3B F3B 1.516(11) 2 ?
O1 C10 1.366(3) . ?
O1 C4 1.383(3) . ?
N1 C12 1.148(3) . ?
N2 C1 1.144(4) . ?
C1 C2 1.438(4) . ?
C2 C3 1.346(4) . ?
C2 C12 1.430(4) . ?
C3 C4 1.430(4) . ?
C4 C5 1.348(3) . ?
C5 C6 1.427(3) . ?
C6 C10 1.370(3) . ?
C6 C7 1.461(3) . ?
C7 C7 1.348(5) 2 ?
C7 C8 1.498(4) . ?
C8 C9 1.504(4) . ?
C9 F3B 1.327(5) 2 ?
C9 F3A 1.403(4) 2 ?
C9 C8 1.504(4) 2 ?
C10 C11 1.474(4) . ?

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
C8 F1B F2B 50.4(3) . . ?
C8 F2B F1B 63.5(5) . . ?
C9 F3B F3B 55.2(3) . 2 ?
C10 O1 C4 106.92(18) . . ?
N2 C1 C2 179.2(4) . . ?
C3 C2 C12 123.5(2) . . ?
C3 C2 C1 120.6(3) . . ?
C12 C2 C1 115.9(2) . . ?
C2 C3 C4 129.2(2) . . ?
C5 C4 O1 109.7(2) . . ?
C5 C4 C3 130.7(2) . . ?
O1 C4 C3 119.5(2) . . ?
C4 C5 C6 107.3(2) . . ?
C10 C6 C5 106.2(2) . . ?
C10 C6 C7 126.7(2) . . ?
C5 C6 C7 127.0(2) . . ?
C7 C7 C6 130.33(13) 2 . ?
C7 C7 C8 110.52(16) 2 . ?
C6 C7 C8 119.1(2) . . ?
F2B C8 F1B 66.1(6) . . ?
F2B C8 C7 122.1(4) . . ?
F1B C8 C7 116.9(3) . . ?
F2B C8 C9 115.8(3) . . ?
F1B C8 C9 126.0(3) . . ?
C7 C8 C9 106.3(3) . . ?
F2B C8 F1A 108.3(6) . . ?
C7 C8 F1A 104.8(3) . . ?
C9 C8 F1A 95.6(3) . . ?
F1B C8 F2A 95.8(5) . . ?
C7 C8 F2A 103.7(3) . . ?
C9 C8 F2A 104.2(3) . . ?
F1A C8 F2A 138.8(5) . . ?
F3B C9 F3B 69.6(6) . 2 ?
F3B C9 F3A 105.2(6) 2 . ?
F3B C9 F3A 105.2(6) . 2 ?
F3A C9 F3A 144.7(6) . 2 ?
F3B C9 C8 113.1(2) . 2 ?
F3B C9 C8 126.6(3) 2 2 ?
F3A C9 C8 105.9(2) . 2 ?
F3A C9 C8 95.2(3) 2 2 ?
F3B C9 C8 126.6(3) . . ?
F3B C9 C8 113.0(2) 2 . ?
F3A C9 C8 95.2(3) . . ?
F3A C9 C8 105.9(2) 2 . ?
C8 C9 C8 106.0(3) 2 . ?
O1 C10 C6 109.9(2) . . ?
O1 C10 C11 115.8(2) . . ?
C6 C10 C11 134.2(2) . . ?
N1 C12 C2 179.5(3) . . ?

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
C12 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
C10 O1 C4 C5 0.4(3) . . . . ?
C10 O1 C4 C3 179.8(2) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C4 O1 -1.2(4) . . . . ?
O1 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 C6 179.5(2) . . . . ?
C4 C5 C6 C10 1.4(3) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C10 C6 C7 C7 -42.6(5) . . . 2 ?
C5 C6 C7 C7 142.0(3) . . . 2 ?
C10 C6 C7 C8 136.4(3) . . . . ?
C5 C6 C7 C8 -38.9(4) . . . . ?
F1B F2B C8 C7 -107.8(5) . . . . ?
F1B F2B C8 C9 119.9(3) . . . . ?
F1B F2B C8 F1A 14.0(3) . . . . ?
F1B F2B C8 F2A -166.8(7) . . . . ?
F2B F1B C8 C7 115.3(5) . . . . ?
F2B F1B C8 C9 -105.5(5) . . . . ?
F2B F1B C8 F1A -160.8(4) . . . . ?
F2B F1B C8 F2A 6.7(4) . . . . ?
C7 C7 C8 F2B -131.3(5) 2 . . . ?
C6 C7 C8 F2B 49.5(6) . . . . ?
C7 C7 C8 F1B 151.3(5) 2 . . . ?
C6 C7 C8 F1B -27.9(6) . . . . ?
C7 C7 C8 C9 4.8(4) 2 . . . ?
C6 C7 C8 C9 -174.5(2) . . . . ?
C7 C7 C8 F1A 105.3(4) 2 . . . ?
C6 C7 C8 F1A -73.9(4) . . . . ?
C7 C7 C8 F2A -104.7(4) 2 . . . ?
C6 C7 C8 F2A 76.0(3) . . . . ?
F3B F3B C9 F3A 150.0(6) 2 . . . ?
F3B F3B C9 F3A -19.7(4) 2 . . 2 ?
F3B F3B C9 C8 -122.2(3) 2 . . 2 ?
F3B F3B C9 C8 104.1(5) 2 . . . ?
F2B C8 C9 F3B -86.3(7) . . . . ?
F1B C8 C9 F3B -8.1(6) . . . . ?
C7 C8 C9 F3B 134.5(4) . . . . ?
F1A C8 C9 F3B 27.2(4) . . . . ?
F2A C8 C9 F3B -116.3(5) . . . . ?
F2B C8 C9 F3B -5.2(5) . . . 2 ?
F1B C8 C9 F3B 73.0(7) . . . 2 ?
C7 C8 C9 F3B -144.4(4) . . . 2 ?
F1A C8 C9 F3B 108.3(5) . . . 2 ?
F2A C8 C9 F3B -35.2(4) . . . 2 ?
F2B C8 C9 F3A -114.2(6) . . . . ?
F1B C8 C9 F3A -36.0(5) . . . . ?
C7 C8 C9 F3A 106.6(3) . . . . ?
F1A C8 C9 F3A -0.7(3) . . . . ?
F2A C8 C9 F3A -144.2(4) . . . . ?
F2B C8 C9 F3A 37.3(5) . . . 2 ?
F1B C8 C9 F3A 115.4(6) . . . 2 ?
C7 C8 C9 F3A -102.0(4) . . . 2 ?
F1A C8 C9 F3A 150.8(5) . . . 2 ?
F2A C8 C9 F3A 7.2(4) . . . 2 ?
F2B C8 C9 C8 137.6(5) . . . 2 ?
F1B C8 C9 C8 -144.2(6) . . . 2 ?
C7 C8 C9 C8 -1.64(13) . . . 2 ?
F1A C8 C9 C8 -108.9(3) . . . 2 ?
F2A C8 C9 C8 107.6(3) . . . 2 ?
C4 O1 C10 C6 0.6(2) . . . . ?
C4 O1 C10 C11 -176.5(2) . . . . ?
C5 C6 C10 O1 -1.2(3) . . . . ?
C7 C6 C10 O1 -177.4(2) . . . . ?
C5 C6 C10 C11 175.0(3) . . . . ?
C7 C6 C10 C11 -1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.82
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1946677'
loop_
_audit_author_name
_audit_author_address
'Thomas Huhn'
;Universitaet Konstanz
Germany
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H34 F6 O4 S2'
_chemical_formula_weight         624.68

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   25.3473(19)
_cell_length_b                   11.0250(8)
_cell_length_c                   10.6805(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2984.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10185
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      27.21

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.390
_exptl_absorpt_coefficient_mu    0.25
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8507
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_process_details   
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            41581
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.607
_diffrn_reflns_theta_max         26.830
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3180
_reflns_number_gt                2771
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0583P)²+1.9941P] 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         3180
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.43398(13) 0.8890(3) 0.5104(3) 0.0729(10) Uani 1 1 d . . . . .
H1A H 0.4005 0.8513 0.5345 0.087 Uiso 1 1 calc R U . . .
H1B H 0.4271 0.9689 0.4737 0.087 Uiso 1 1 calc R U . . .
H1C H 0.4564 0.8980 0.5845 0.087 Uiso 1 1 calc R U . . .
C2 C 0.46094(9) 0.81168(19) 0.41756(18) 0.0390(5) Uani 1 1 d . . . . .
H2A H 0.4680 0.7321 0.4570 0.047 Uiso 1 1 calc R U . . .
H2B H 0.4955 0.8491 0.3982 0.047 Uiso 1 1 calc R U . . .
C3 C 0.43268(7) 0.78953(16) 0.29632(16) 0.0261(4) Uani 1 1 d . . . . .
C4 C 0.43801(6) 0.69469(15) 0.21355(15) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.47446(7) 0.59292(15) 0.23127(15) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.45518(8) 0.46631(18) 0.2107(2) 0.0419(5) Uani 1 1 d . . . . .
C7 C 0.5000 0.3834(2) 0.2500 0.0239(5) Uani 1 2 d S T P A .
C8 C 0.40355(6) 0.70523(15) 0.10764(15) 0.0216(3) Uani 1 1 d . . . . .
H8A H 0.4019 0.6470 0.0422 0.026 Uiso 1 1 calc R U . . .
C9 C 0.37359(7) 0.80696(15) 0.11081(15) 0.0228(3) Uani 1 1 d . . . . .
C10 C 0.33639(6) 0.85407(15) 0.01351(15) 0.0226(3) Uani 1 1 d . . . . .
H10A H 0.3571 0.8949 -0.0541 0.027 Uiso 1 1 calc R U . . .
C11 C 0.26896(7) 0.99313(16) -0.02223(16) 0.0253(4) Uani 1 1 d . . . . .
H11B H 0.2906 1.0375 -0.0844 0.030 Uiso 1 1 calc R U . . .
H11A H 0.2450 1.0521 0.0185 0.030 Uiso 1 1 calc R U . . .
C12 C 0.23632(7) 0.89656(16) -0.08903(16) 0.0247(4) Uani 1 1 d . . . . .
C13 C 0.27480(7) 0.80125(16) -0.13758(16) 0.0260(4) Uani 1 1 d . . . . .
H13B H 0.2548 0.7329 -0.1744 0.031 Uiso 1 1 calc R U . . .
H13A H 0.2969 0.8372 -0.2043 0.031 Uiso 1 1 calc R U . . .
C14 C 0.20803(8) 0.95587(18) -0.19954(18) 0.0332(4) Uani 1 1 d . . . . .
H14C H 0.1841 1.0189 -0.1686 0.040 Uiso 1 1 calc R U . . .
H14A H 0.1877 0.8944 -0.2451 0.040 Uiso 1 1 calc R U . . .
H14B H 0.2341 0.9924 -0.2559 0.040 Uiso 1 1 calc R U . . .
C15 C 0.19642(7) 0.83961(19) 0.00058(19) 0.0347(4) Uani 1 1 d . . . . .
H15A H 0.2151 0.8017 0.0707 0.042 Uiso 1 1 calc R U . . .
H15B H 0.1758 0.7780 -0.0440 0.042 Uiso 1 1 calc R U . . .
H15C H 0.1727 0.9026 0.0325 0.042 Uiso 1 1 calc R U . . .
O1 O 0.30829(5) 0.75646(11) -0.03835(11) 0.0249(3) Uani 1 1 d . . . . .
O2 O 0.30302(5) 0.93987(11) 0.07068(11) 0.0249(3) Uani 1 1 d . . . . .
S1 S 0.38578(2) 0.89081(4) 0.24360(4) 0.02747(14) Uani 1 1 d . . . . .
F1 F 0.41691(10) 0.4422(2) 0.3212(3) 0.0379(9) Uani 0.502(5) 1 d . . P A 1
F2 F 0.42831(12) 0.4394(2) 0.1204(3) 0.0366(10) Uani 0.502(5) 1 d . . P A 1
F3 F 0.50916(11) 0.2842(3) 0.1824(3) 0.0354(8) Uani 0.502(5) 1 d . . P A 1
F4 F 0.40843(9) 0.4409(2) 0.2297(3) 0.0373(10) Uani 0.498(5) 1 d . . P A 2
F5 F 0.45784(15) 0.4513(2) 0.0652(3) 0.0349(9) Uani 0.498(5) 1 d . . P A 2
F6 F 0.51961(10) 0.3456(4) 0.1371(3) 0.0370(9) Uani 0.498(5) 1 d . . P A 2


_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 1.475(3) . ?
C2 C3 1.500(2) . ?
C3 C4 1.376(2) . ?
C3 S1 1.7254(17) . ?
C4 C8 1.434(2) . ?
C4 C5 1.466(2) . ?
C5 C5 1.355(3) 4_655 ?
C5 C6 1.495(2) . ?
C6 F2 1.217(3) . ?
C6 F4 1.234(3) . ?
C6 C7 1.517(2) . ?
C6 F1 1.551(4) . ?
C6 F5 1.564(4) . ?
C7 F3 1.331(3) 4_655 ?
C7 F3 1.331(3) . ?
C7 F6 1.369(3) . ?
C7 F6 1.369(3) 4_655 ?
C7 C6 1.517(2) 4_655 ?
C8 C9 1.355(2) . ?
C9 C10 1.496(2) . ?
C9 S1 1.7209(17) . ?
C10 O1 1.404(2) . ?
C10 O2 1.408(2) . ?
C11 O2 1.4405(19) . ?
C11 C12 1.525(2) . ?
C12 C13 1.525(2) . ?
C12 C15 1.527(2) . ?
C12 C14 1.528(2) . ?
C13 O1 1.445(2) . ?
F3 F3 1.516(7) 4_655 ?

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
C1 C2 C3 116.94(18) . . ?
C4 C3 C2 129.16(16) . . ?
C4 C3 S1 110.48(13) . . ?
C2 C3 S1 120.36(13) . . ?
C3 C4 C8 112.67(15) . . ?
C3 C4 C5 124.11(15) . . ?
C8 C4 C5 123.23(15) . . ?
C5 C5 C4 129.82(9) 4_655 . ?
C5 C5 C6 110.85(10) 4_655 . ?
C4 C5 C6 119.31(14) . . ?
F2 C6 C5 121.8(2) . . ?
F4 C6 C5 120.1(2) . . ?
F2 C6 C7 119.5(2) . . ?
F4 C6 C7 122.4(2) . . ?
C5 C6 C7 106.06(15) . . ?
F2 C6 F1 102.2(2) . . ?
C5 C6 F1 104.63(19) . . ?
C7 C6 F1 98.86(18) . . ?
F4 C6 F5 100.4(2) . . ?
C5 C6 F5 103.37(19) . . ?
C7 C6 F5 100.30(17) . . ?
F3 C7 F3 69.4(4) 4_655 . ?
F6 C7 F6 144.5(4) . 4_655 ?
F3 C7 C6 120.96(16) 4_655 . ?
F3 C7 C6 118.40(14) . . ?
F6 C7 C6 102.22(17) . . ?
F6 C7 C6 98.94(18) 4_655 . ?
F3 C7 C6 118.40(14) 4_655 4_655 ?
F3 C7 C6 120.97(16) . 4_655 ?
F6 C7 C6 98.94(18) . 4_655 ?
F6 C7 C6 102.22(17) 4_655 4_655 ?
C6 C7 C6 105.9(2) . 4_655 ?
C9 C8 C4 112.88(15) . . ?
C8 C9 C10 128.55(15) . . ?
C8 C9 S1 111.39(13) . . ?
C10 C9 S1 119.94(12) . . ?
O1 C10 O2 112.41(13) . . ?
O1 C10 C9 109.12(13) . . ?
O2 C10 C9 108.09(13) . . ?
O2 C11 C12 111.27(13) . . ?
C13 C12 C11 107.04(14) . . ?
C13 C12 C15 110.69(15) . . ?
C11 C12 C15 110.67(15) . . ?
C13 C12 C14 109.41(15) . . ?
C11 C12 C14 108.48(14) . . ?
C15 C12 C14 110.45(15) . . ?
O1 C13 C12 111.22(14) . . ?
C10 O1 C13 108.99(12) . . ?
C10 O2 C11 109.58(12) . . ?
C9 S1 C3 92.57(8) . . ?
C7 F3 F3 55.29(19) . 4_655 ?

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
C1 C2 C3 C4 -155.8(3) . . . . ?
C1 C2 C3 S1 24.0(3) . . . . ?
C2 C3 C4 C8 179.58(19) . . . . ?
S1 C3 C4 C8 -0.20(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
S1 C3 C4 C5 -179.68(13) . . . . ?
C3 C4 C5 C5 -44.3(3) . . . 4_655 ?
C8 C4 C5 C5 136.2(2) . . . 4_655 ?
C3 C4 C5 C6 133.5(2) . . . . ?
C8 C4 C5 C6 -45.9(3) . . . . ?
C5 C5 C6 F2 -137.0(3) 4_655 . . . ?
C4 C5 C6 F2 44.7(4) . . . . ?
C5 C5 C6 F4 148.6(3) 4_655 . . . ?
C4 C5 C6 F4 -29.7(4) . . . . ?
C5 C5 C6 C7 4.3(3) 4_655 . . . ?
C4 C5 C6 C7 -173.97(14) . . . . ?
C5 C5 C6 F1 108.2(2) 4_655 . . . ?
C4 C5 C6 F1 -70.0(2) . . . . ?
C5 C5 C6 F5 -100.8(2) 4_655 . . . ?
C4 C5 C6 F5 81.0(2) . . . . ?
F2 C6 C7 F3 -80.6(4) . . . 4_655 ?
F4 C6 C7 F3 -6.3(4) . . . 4_655 ?
C5 C6 C7 F3 137.0(2) . . . 4_655 ?
F1 C6 C7 F3 28.8(3) . . . 4_655 ?
F5 C6 C7 F3 -115.8(3) . . . 4_655 ?
F2 C6 C7 F3 1.2(3) . . . . ?
F4 C6 C7 F3 75.6(3) . . . . ?
C5 C6 C7 F3 -141.2(3) . . . . ?
F1 C6 C7 F3 110.7(2) . . . . ?
F5 C6 C7 F3 -33.9(3) . . . . ?
F2 C6 C7 F6 37.8(3) . . . . ?
F4 C6 C7 F6 112.1(3) . . . . ?
C5 C6 C7 F6 -104.6(2) . . . . ?
F1 C6 C7 F6 147.3(2) . . . . ?
F5 C6 C7 F6 2.7(2) . . . . ?
F2 C6 C7 F6 -113.5(3) . . . 4_655 ?
F4 C6 C7 F6 -39.2(4) . . . 4_655 ?
C5 C6 C7 F6 104.1(2) . . . 4_655 ?
F1 C6 C7 F6 -4.1(3) . . . 4_655 ?
F5 C6 C7 F6 -148.7(3) . . . 4_655 ?
F2 C6 C7 C6 140.9(3) . . . 4_655 ?
F4 C6 C7 C6 -144.7(3) . . . 4_655 ?
C5 C6 C7 C6 -1.47(9) . . . 4_655 ?
F1 C6 C7 C6 -109.58(18) . . . 4_655 ?
F5 C6 C7 C6 105.80(19) . . . 4_655 ?
C3 C4 C8 C9 0.8(2) . . . . ?
C5 C4 C8 C9 -179.74(15) . . . . ?
C4 C8 C9 C10 174.86(16) . . . . ?
C4 C8 C9 S1 -0.99(18) . . . . ?
C8 C9 C10 O1 40.2(2) . . . . ?
S1 C9 C10 O1 -144.22(12) . . . . ?
C8 C9 C10 O2 162.76(16) . . . . ?
S1 C9 C10 O2 -21.69(18) . . . . ?
O2 C11 C12 C13 -52.98(18) . . . . ?
O2 C11 C12 C15 67.73(18) . . . . ?
O2 C11 C12 C14 -170.95(14) . . . . ?
C11 C12 C13 O1 53.57(18) . . . . ?
C15 C12 C13 O1 -67.12(18) . . . . ?
C14 C12 C13 O1 170.93(14) . . . . ?
O2 C10 O1 C13 63.62(17) . . . . ?
C9 C10 O1 C13 -176.48(13) . . . . ?
C12 C13 O1 C10 -58.88(17) . . . . ?
O1 C10 O2 C11 -63.32(17) . . . . ?
C9 C10 O2 C11 176.18(13) . . . . ?
C12 C11 O2 C10 57.83(18) . . . . ?
C8 C9 S1 C3 0.75(14) . . . . ?
C10 C9 S1 C3 -175.51(14) . . . . ?
C4 C3 S1 C9 -0.30(14) . . . . ?
C2 C3 S1 C9 179.89(17) . . . . ?
F6 C7 F3 F3 172.9(3) . . . 4_655 ?
F6 C7 F3 F3 -4.5(2) 4_655 . . 4_655 ?
C6 C7 F3 F3 -114.95(19) . . . 4_655 ?
C6 C7 F3 F3 111.5(2) 4_655 . . 4_655 ?

_refine_diff_density_max         1.091
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2016261'
loop_
_audit_author_name
_audit_author_address
'Thomas Huhn'
;Universitaet Konstanz
Germany
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H10 F6 O2'
_chemical_formula_weight         384.27

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'
F F 0.0171 0.0103 '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      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                   7.1470(10)
_cell_length_b                   8.3925(12)
_cell_length_c                   14.495(2)
_cell_angle_alpha                81.952(12)
_cell_angle_beta                 87.947(12)
_cell_angle_gamma                78.899(12)
_cell_volume                     844.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13031
_cell_measurement_theta_min      1.42
_cell_measurement_theta_max      24.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.667
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_process_details   
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            9373
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.419
_diffrn_reflns_theta_max         24.716
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             2841
_reflns_number_gt                1980
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0562P)²] 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         2841
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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 1.0134(2) 0.70657(17) 0.45553(8) 0.0566(4) Uani 1 1 d . . . . .
F2 F 0.78983(18) 0.90439(17) 0.40243(9) 0.0518(4) Uani 1 1 d . . . . .
F5 F 1.38047(17) 0.87070(19) 0.27299(12) 0.0671(5) Uani 1 1 d . . . . .
F6 F 1.1635(2) 1.06705(16) 0.21643(10) 0.0660(4) Uani 1 1 d . . . . .
O1 O 1.23227(18) 0.61202(17) 0.01988(9) 0.0335(3) Uani 1 1 d . . . . .
O2 O 0.59297(18) 0.53683(17) 0.23153(9) 0.0349(4) Uani 1 1 d . . . . .
C1 C 1.3350(3) 0.8518(3) -0.18406(16) 0.0436(6) Uani 1 1 d . . . . .
H1 H 1.3708 0.8811 -0.2455 0.052 Uiso 1 1 calc R U . . .
C2 C 1.2896(3) 0.8147(3) -0.10599(15) 0.0362(5) Uani 1 1 d . . . . .
C3 C 1.2362(3) 0.7752(2) -0.01140(13) 0.0313(5) Uani 1 1 d . . . . .
C4 C 1.1890(3) 0.8645(3) 0.05880(13) 0.0296(4) Uani 1 1 d . . . . .
H4 H 1.1831 0.9768 0.0559 0.035 Uiso 1 1 calc R U . . .
C5 C 1.1494(2) 0.7554(2) 0.13876(13) 0.0281(4) Uani 1 1 d . . . . .
C6 C 1.1798(3) 0.6031(3) 0.11160(14) 0.0317(5) Uani 1 1 d . . . . .
C7 C 1.1707(3) 0.4375(3) 0.15941(15) 0.0387(5) Uani 1 1 d . . . . .
H7A H 1.1724 0.4374 0.2256 0.058 Uiso 1 1 calc R U . . .
H7B H 1.2785 0.3607 0.1411 0.058 Uiso 1 1 calc R U . . .
H7C H 1.0552 0.4065 0.1426 0.058 Uiso 1 1 calc R U . . .
C8 C 1.0938(3) 0.7997(2) 0.23130(13) 0.0284(4) Uani 1 1 d . . . . .
C9 C 1.1906(3) 0.9199(3) 0.26957(14) 0.0332(5) Uani 1 1 d . . . . .
C10 C 1.1073(4) 0.9377(4) 0.36570(17) 0.0579(7) Uani 1 1 d . . . . .
C11 C 0.9638(3) 0.8214(3) 0.38115(14) 0.0375(5) Uani 1 1 d . . . . .
C12 C 0.9633(3) 0.7491(3) 0.29232(13) 0.0306(5) Uani 1 1 d . . . . .
C13 C 0.8237(3) 0.6457(2) 0.28402(13) 0.0305(5) Uani 1 1 d . . . . .
C14 C 0.7191(3) 0.6399(2) 0.20787(14) 0.0307(5) Uani 1 1 d . . . . .
C15 C 0.7070(3) 0.7233(3) 0.11116(14) 0.0356(5) Uani 1 1 d . . . . .
H15A H 0.7576 0.8220 0.1075 0.053 Uiso 1 1 calc R U . . .
H15B H 0.5761 0.7501 0.0921 0.053 Uiso 1 1 calc R U . . .
H15C H 0.7793 0.6522 0.0709 0.053 Uiso 1 1 calc R U . . .
C16 C 0.7557(3) 0.5410(3) 0.35930(15) 0.0382(5) Uani 1 1 d . . . . .
H16 H 0.7986 0.5206 0.4204 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6184(3) 0.4783(3) 0.32474(14) 0.0383(5) Uani 1 1 d . . . . .
C18 C 0.5005(3) 0.3691(3) 0.36661(16) 0.0478(6) Uani 1 1 d . . . . .
C19 C 0.4059(4) 0.2784(4) 0.40433(18) 0.0661(8) Uani 1 1 d . . . . .
H19 H 0.3314 0.2068 0.4341 0.079 Uiso 1 1 calc R U . . .
F3A F 1.2067(14) 0.9454(11) 0.4314(3) 0.052(2) Uani 0.480(18) 1 d . . P A 1
F4A F 1.073(2) 1.0639(17) 0.3956(10) 0.085(4) Uani 0.480(18) 1 d . . P A 1
F3B F 1.2765(12) 0.844(3) 0.4262(4) 0.104(4) Uani 0.520(18) 1 d . . P A 2
F4B F 0.9830(11) 1.1069(5) 0.3525(6) 0.0515(18) Uani 0.520(18) 1 d . . P A 2


_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 C11 1.350(3) . ?
F2 C11 1.351(2) . ?
F5 C9 1.341(2) . ?
F6 C9 1.345(2) . ?
O1 C6 1.364(2) . ?
O1 C3 1.386(2) . ?
O2 C14 1.369(2) . ?
O2 C17 1.377(2) . ?
C1 C2 1.182(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.421(3) . ?
C3 C4 1.343(3) . ?
C4 C5 1.429(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(3) . ?
C5 C8 1.463(3) . ?
C6 C7 1.476(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C12 1.349(3) . ?
C8 C9 1.502(3) . ?
C9 C10 1.511(3) . ?
C10 F4A 1.179(8) . ?
C10 F3A 1.225(6) . ?
C10 F4B 1.514(6) . ?
C10 C11 1.537(3) . ?
C10 F3B 1.538(10) . ?
C11 C12 1.498(3) . ?
C12 C13 1.462(3) . ?
C13 C14 1.367(3) . ?
C13 C16 1.434(3) . ?
C14 C15 1.474(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.341(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.422(3) . ?
C18 C19 1.179(3) . ?
C19 H19 0.9300 . ?
F3A F4A 1.30(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
C6 O1 C3 106.84(15) . . ?
C14 O2 C17 107.00(15) . . ?
C2 C1 H1 180.0 . . ?
C1 C2 C3 178.1(2) . . ?
C4 C3 O1 109.62(17) . . ?
C4 C3 C2 133.3(2) . . ?
O1 C3 C2 117.11(17) . . ?
C3 C4 C5 107.39(18) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
C6 C5 C4 106.09(17) . . ?
C6 C5 C8 127.66(18) . . ?
C4 C5 C8 126.22(18) . . ?
O1 C6 C5 110.04(17) . . ?
O1 C6 C7 115.67(17) . . ?
C5 C6 C7 134.28(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C8 C5 130.20(18) . . ?
C12 C8 C9 110.97(17) . . ?
C5 C8 C9 118.83(16) . . ?
F5 C9 F6 104.70(18) . . ?
F5 C9 C8 112.21(16) . . ?
F6 C9 C8 112.58(17) . . ?
F5 C9 C10 111.03(19) . . ?
F6 C9 C10 109.82(19) . . ?
C8 C9 C10 106.57(16) . . ?
F4A C10 F3A 65.6(14) . . ?
F4A C10 C9 123.1(6) . . ?
F3A C10 C9 121.8(4) . . ?
C9 C10 F4B 103.1(3) . . ?
F4A C10 C11 119.5(4) . . ?
F3A C10 C11 117.9(3) . . ?
C9 C10 C11 105.42(18) . . ?
F4B C10 C11 103.9(3) . . ?
C9 C10 F3B 100.4(5) . . ?
F4B C10 F3B 138.0(11) . . ?
C11 C10 F3B 102.7(5) . . ?
F1 C11 F2 105.32(17) . . ?
F1 C11 C12 112.69(18) . . ?
F2 C11 C12 112.22(16) . . ?
F1 C11 C10 110.53(19) . . ?
F2 C11 C10 110.2(2) . . ?
C12 C11 C10 105.91(17) . . ?
C8 C12 C13 131.35(18) . . ?
C8 C12 C11 111.01(17) . . ?
C13 C12 C11 117.59(16) . . ?
C14 C13 C16 106.31(17) . . ?
C14 C13 C12 128.10(18) . . ?
C16 C13 C12 125.31(17) . . ?
C13 C14 O2 109.59(17) . . ?
C13 C14 C15 134.86(18) . . ?
O2 C14 C15 115.47(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 106.90(18) . . ?
C17 C16 H16 126.5 . . ?
C13 C16 H16 126.5 . . ?
C16 C17 O2 110.19(18) . . ?
C16 C17 C18 132.0(2) . . ?
O2 C17 C18 117.78(18) . . ?
C19 C18 C17 177.6(3) . . ?
C18 C19 H19 180.0 . . ?
C10 F3A F4A 55.5(7) . . ?
C10 F4A F3A 58.9(9) . . ?

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
C6 O1 C3 C4 0.4(2) . . . . ?
C6 O1 C3 C2 179.40(16) . . . . ?
O1 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C5 -179.8(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C8 179.46(17) . . . . ?
C3 O1 C6 C5 0.4(2) . . . . ?
C3 O1 C6 C7 -178.77(16) . . . . ?
C4 C5 C6 O1 -1.0(2) . . . . ?
C8 C5 C6 O1 -179.18(16) . . . . ?
C4 C5 C6 C7 177.9(2) . . . . ?
C8 C5 C6 C7 -0.2(4) . . . . ?
C6 C5 C8 C12 -42.9(3) . . . . ?
C4 C5 C8 C12 139.3(2) . . . . ?
C6 C5 C8 C9 137.1(2) . . . . ?
C4 C5 C8 C9 -40.7(3) . . . . ?
C12 C8 C9 F5 123.0(2) . . . . ?
C5 C8 C9 F5 -57.0(2) . . . . ?
C12 C8 C9 F6 -119.21(19) . . . . ?
C5 C8 C9 F6 60.8(2) . . . . ?
C12 C8 C9 C10 1.2(2) . . . . ?
C5 C8 C9 C10 -178.75(19) . . . . ?
F5 C9 C10 F4A 96.5(11) . . . . ?
F6 C9 C10 F4A -18.8(11) . . . . ?
C8 C9 C10 F4A -141.0(11) . . . . ?
F5 C9 C10 F3A 16.6(6) . . . . ?
F6 C9 C10 F3A -98.7(6) . . . . ?
C8 C9 C10 F3A 139.1(5) . . . . ?
F5 C9 C10 F4B 129.9(4) . . . . ?
F6 C9 C10 F4B 14.6(4) . . . . ?
C8 C9 C10 F4B -107.6(4) . . . . ?
F5 C9 C10 C11 -121.4(2) . . . . ?
F6 C9 C10 C11 123.3(2) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
F5 C9 C10 F3B -15.0(7) . . . . ?
F6 C9 C10 F3B -130.3(7) . . . . ?
C8 C9 C10 F3B 107.5(6) . . . . ?
F4A C10 C11 F1 -96.7(12) . . . . ?
F3A C10 C11 F1 -20.4(7) . . . . ?
C9 C10 C11 F1 119.5(2) . . . . ?
F4B C10 C11 F1 -132.4(4) . . . . ?
F3B C10 C11 F1 14.9(6) . . . . ?
F4A C10 C11 F2 19.4(12) . . . . ?
F3A C10 C11 F2 95.6(6) . . . . ?
C9 C10 C11 F2 -124.4(2) . . . . ?
F4B C10 C11 F2 -16.3(4) . . . . ?
F3B C10 C11 F2 130.9(6) . . . . ?
F4A C10 C11 C12 141.0(12) . . . . ?
F3A C10 C11 C12 -142.7(6) . . . . ?
C9 C10 C11 C12 -2.8(3) . . . . ?
F4B C10 C11 C12 105.3(4) . . . . ?
F3B C10 C11 C12 -107.5(6) . . . . ?
C5 C8 C12 C13 -6.0(4) . . . . ?
C9 C8 C12 C13 174.0(2) . . . . ?
C5 C8 C12 C11 176.81(19) . . . . ?
C9 C8 C12 C11 -3.2(2) . . . . ?
F1 C11 C12 C8 -117.2(2) . . . . ?
F2 C11 C12 C8 124.13(19) . . . . ?
C10 C11 C12 C8 3.8(3) . . . . ?
F1 C11 C12 C13 65.2(2) . . . . ?
F2 C11 C12 C13 -53.5(2) . . . . ?
C10 C11 C12 C13 -173.8(2) . . . . ?
C8 C12 C13 C14 -37.2(4) . . . . ?
C11 C12 C13 C14 139.9(2) . . . . ?
C8 C12 C13 C16 149.8(2) . . . . ?
C11 C12 C13 C16 -33.2(3) . . . . ?
C16 C13 C14 O2 -0.7(2) . . . . ?
C12 C13 C14 O2 -174.81(18) . . . . ?
C16 C13 C14 C15 175.8(2) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C17 O2 C14 C13 0.6(2) . . . . ?
C17 O2 C14 C15 -176.72(17) . . . . ?
C14 C13 C16 C17 0.6(2) . . . . ?
C12 C13 C16 C17 174.9(2) . . . . ?
C13 C16 C17 O2 -0.3(2) . . . . ?
C13 C16 C17 C18 -179.5(2) . . . . ?
C14 O2 C17 C16 -0.2(2) . . . . ?
C14 O2 C17 C18 179.15(19) . . . . ?
C9 C10 F3A F4A 115.2(4) . . . . ?
F4B C10 F3A F4A 1.3(4) . . . . ?
C11 C10 F3A F4A -111.8(5) . . . . ?
F3B C10 F3A F4A 175.9(7) . . . . ?
C9 C10 F4A F3A -113.3(6) . . . . ?
F4B C10 F4A F3A -177.9(6) . . . . ?
C11 C10 F4A F3A 109.6(7) . . . . ?
F3B C10 F4A F3A -2.4(4) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1946676'
loop_
_audit_author_name
_audit_author_address
'Thomas Huhn'
;Universitaet Konstanz
Germany
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N4 O2'
_chemical_formula_sum            'C23 H16 N4 O2'
_chemical_formula_weight         380.40

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 2yc'

_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+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'

_cell_length_a                   21.831(3)
_cell_length_b                   9.0389(8)
_cell_length_c                   10.1044(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.746(10)
_cell_angle_gamma                90
_cell_volume                     1952.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16564
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      26.59

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.750
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9430
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   
;
'X-SHAPE 2.07 (03-Aug-2005) Stoe & Cie, Darmstadt, Germany'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            11920
_diffrn_reflns_av_unetI/netI     0.2335
_diffrn_reflns_av_R_equivalents  0.2671
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.906
_diffrn_reflns_theta_max         26.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1960
_reflns_number_gt                1477
_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    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0834P)²+0.2911P] 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         1960
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.006
_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
O2 O 0.12383(6) 0.09445(15) 0.76972(13) 0.0338(4) Uani 1 1 d . . . . .
N3 N 0.19379(8) -0.2181(2) 0.80388(17) 0.0403(4) Uani 1 1 d . . . . .
C3 C 0.19022(9) 0.1015(2) 0.60440(19) 0.0347(5) Uani 1 1 d . . . . .
H3 H 0.2025 0.1577 0.5372 0.042 Uiso 1 1 calc R U . . .
C4 C 0.26829(10) -0.0710(2) 0.5602(2) 0.0371(5) Uani 1 1 d . . . . .
C5 C 0.14372(9) 0.1666(2) 0.66541(18) 0.0332(4) Uani 1 1 d . . . . .
C6 C 0.02941(9) 0.4346(2) 0.73955(19) 0.0343(5) Uani 1 1 d . . . . .
C7 C 0.07086(9) 0.3091(2) 0.73025(19) 0.0324(4) Uani 1 1 d . . . . .
N9 N 0.30776(9) -0.0999(2) 0.50495(19) 0.0469(5) Uani 1 1 d . . . . .
C9 C 0.11300(9) 0.2972(2) 0.64005(19) 0.0351(5) Uani 1 1 d . . . . .
H9 H 0.1185 0.3665 0.5754 0.042 Uiso 1 1 calc R U . . .
C10 C 0.20535(9) -0.1346(2) 0.72706(19) 0.0339(5) Uani 1 1 d . . . . .
C11 C 0.07996(9) 0.1838(2) 0.80809(18) 0.0324(4) Uani 1 1 d . . . . .
C12 C 0.05503(10) 0.1304(2) 0.9255(2) 0.0408(5) Uani 1 1 d . . . . .
H12C H 0.0303 0.2068 0.9548 0.049 Uiso 1 1 calc R U . . .
H12B H 0.0892 0.1052 0.9980 0.049 Uiso 1 1 calc R U . . .
H12A H 0.0295 0.0445 0.8997 0.049 Uiso 1 1 calc R U . . .
C13 C 0.21926(9) -0.0306(2) 0.63018(19) 0.0339(5) Uani 1 1 d . . . . .
C14 C 0.0000 0.6876(4) 0.7500 0.0552(9) Uani 1 2 d S T P . .
H14B H -0.0142 0.7504 0.6719 0.066 Uiso 0.5 1 calc R U P . .
H14A H 0.0142 0.7504 0.8281 0.066 Uiso 0.5 1 calc R U P . .
C15 C 0.05291(12) 0.5898(2) 0.7264(3) 0.0514(6) Uani 1 1 d . . . . .
H15A H 0.0615 0.6061 0.6371 0.062 Uiso 1 1 calc R U . . .
H15B H 0.0907 0.6085 0.7934 0.062 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
O2 C11 1.368(2) . ?
O2 C5 1.382(2) . ?
N3 C10 1.147(3) . ?
C3 C13 1.353(3) . ?
C3 C5 1.418(3) . ?
C4 N9 1.148(3) . ?
C4 C13 1.445(3) . ?
C5 C9 1.356(3) . ?
C6 C6 1.343(4) 2_556 ?
C6 C7 1.466(3) . ?
C6 C15 1.509(3) . ?
C7 C11 1.370(3) . ?
C7 C9 1.425(3) . ?
C10 C13 1.434(3) . ?
C11 C12 1.483(3) . ?
C14 C15 1.512(3) . ?
C14 C15 1.512(3) 2_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
C11 O2 C5 106.53(15) . . ?
C13 C3 C5 129.15(18) . . ?
N9 C4 C13 178.4(2) . . ?
C9 C5 O2 109.54(17) . . ?
C9 C5 C3 130.46(17) . . ?
O2 C5 C3 119.99(17) . . ?
C6 C6 C7 129.22(11) 2_556 . ?
C6 C6 C15 111.52(12) 2_556 . ?
C7 C6 C15 119.25(18) . . ?
C11 C7 C9 105.54(17) . . ?
C11 C7 C6 128.47(18) . . ?
C9 C7 C6 125.92(17) . . ?
C5 C9 C7 107.68(17) . . ?
N3 C10 C13 179.5(2) . . ?
O2 C11 C7 110.69(16) . . ?
O2 C11 C12 115.26(16) . . ?
C7 C11 C12 133.98(18) . . ?
C3 C13 C10 123.67(17) . . ?
C3 C13 C4 119.61(18) . . ?
C10 C13 C4 116.71(18) . . ?
C15 C14 C15 108.4(3) . 2_556 ?
C6 C15 C14 104.23(19) . . ?

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
C11 O2 C5 C9 0.1(2) . . . . ?
C11 O2 C5 C3 179.37(17) . . . . ?
C13 C3 C5 C9 -178.6(2) . . . . ?
C13 C3 C5 O2 2.3(3) . . . . ?
C6 C6 C7 C11 -41.8(4) 2_556 . . . ?
C15 C6 C7 C11 137.4(2) . . . . ?
C6 C6 C7 C9 141.7(3) 2_556 . . . ?
C15 C6 C7 C9 -39.1(3) . . . . ?
O2 C5 C9 C7 -0.9(2) . . . . ?
C3 C5 C9 C7 179.92(19) . . . . ?
C11 C7 C9 C5 1.3(2) . . . . ?
C6 C7 C9 C5 178.52(18) . . . . ?
C5 O2 C11 C7 0.8(2) . . . . ?
C5 O2 C11 C12 -176.55(17) . . . . ?
C9 C7 C11 O2 -1.3(2) . . . . ?
C6 C7 C11 O2 -178.41(18) . . . . ?
C9 C7 C11 C12 175.4(2) . . . . ?
C6 C7 C11 C12 -1.7(4) . . . . ?
C5 C3 C13 C10 2.0(3) . . . . ?
C5 C3 C13 C4 -176.44(19) . . . . ?
C6 C6 C15 C14 2.9(3) 2_556 . . . ?
C7 C6 C15 C14 -176.45(15) . . . . ?
C15 C14 C15 C6 -0.97(10) 2_556 . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

