# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

####################################################################### 
# 
# 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_Ofer10
_database_code_depnum_ccdc_archive 'CCDC 1058391'
_audit_update_record             
;
2015-04-08 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        semiaza-glycoluril
_chemical_name_common            Ofer10
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H20 N5 O1, C1 F3 O3 S'
_chemical_formula_sum            'C12 H20 F3 N5 O4 S'
_chemical_formula_weight         387.39
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4770(5)
_cell_length_b                   10.5840(11)
_cell_length_c                   12.7780(14)
_cell_angle_alpha                85.883(5)
_cell_angle_beta                 86.565(6)
_cell_angle_gamma                75.600(6)
_cell_volume                     845.45(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2369
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      24.14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_process_details   
;
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean 95
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            2442
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         24.14
_reflns_number_total             2442
_reflns_number_gt                2270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius, 2006)'
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 3.5'
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0507P)²+3.8689P] 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         2442
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2240
_refine_ls_wR_factor_gt          0.2142
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_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
S1 S 0.3466(2) 0.87216(16) 0.23469(12) 0.0437(5) Uani 1 1 d . . .
O1 O 1.2640(6) 0.4129(4) 0.1082(3) 0.0437(11) Uani 1 1 d . . .
O2 O 0.5157(8) 0.8881(7) 0.2931(5) 0.090(2) Uani 1 1 d . . .
N1 N 0.9992(7) 0.3206(4) 0.0590(3) 0.0347(11) Uani 1 1 d . . .
N2 N 0.9146(7) 0.4792(4) 0.1686(4) 0.0363(11) Uani 1 1 d . . .
N3 N 0.6495(7) 0.3723(4) 0.2545(3) 0.0309(10) Uani 1 1 d . . .
N4 N 0.7094(7) 0.2276(4) 0.1317(3) 0.0300(10) Uani 1 1 d . . .
N5 N 0.5700(8) 0.1659(5) 0.2938(4) 0.0396(12) Uani 1 1 d . . .
H5 H 0.5375 0.1017 0.2634 0.048 Uiso 1 1 calc R . .
C1 C 1.0788(8) 0.4045(5) 0.1121(4) 0.0331(12) Uani 1 1 d . . .
C2 C 0.9445(10) 0.5679(6) 0.2443(5) 0.0437(14) Uani 1 1 d . . .
H2A H 0.8056 0.6121 0.2754 0.066 Uiso 0.50 1 calc PR . .
H2B H 1.0134 0.6330 0.2091 0.066 Uiso 0.50 1 calc PR . .
H2C H 1.0349 0.5186 0.2997 0.066 Uiso 0.50 1 calc PR . .
H2D H 0.9285 0.5373 0.3190 0.066 Uiso 0.50 1 d PR . .
H2E H 1.0738 0.5741 0.2335 0.066 Uiso 0.50 1 d PR . .
H2F H 0.8457 0.6425 0.2280 0.066 Uiso 0.50 1 d PR . .
C3 C 0.7181(8) 0.4421(5) 0.1595(4) 0.0321(12) Uani 1 1 d . . .
H3 H 0.6019 0.5185 0.1361 0.038 Uiso 1 1 calc R . .
C4 C 0.5197(10) 0.4500(6) 0.3353(5) 0.0473(16) Uani 1 1 d . . .
H4A H 0.5597 0.5332 0.3368 0.071 Uiso 0.50 1 calc PR . .
H4B H 0.5434 0.4022 0.4039 0.071 Uiso 0.50 1 calc PR . .
H4C H 0.3686 0.4668 0.3197 0.071 Uiso 0.50 1 calc PR . .
H4D H 0.4644 0.5269 0.2992 0.071 Uiso 0.50 1 d PR . .
H4E H 0.6032 0.4564 0.3919 0.071 Uiso 0.50 1 d PR . .
H4F H 0.4120 0.4166 0.3622 0.071 Uiso 0.50 1 d PR . .
C5 C 0.6393(8) 0.2521(5) 0.2302(4) 0.0309(12) Uani 1 1 d . . .
C6 C 0.7187(10) 0.1067(6) 0.0829(5) 0.0437(14) Uani 1 1 d . . .
H6A H 0.7768 0.1120 0.0106 0.066 Uiso 1 1 calc R . .
H6B H 0.5748 0.0927 0.0825 0.066 Uiso 1 1 calc R . .
H6C H 0.8107 0.0338 0.1226 0.066 Uiso 1 1 calc R . .
C7 C 0.7727(8) 0.3390(5) 0.0774(4) 0.0318(12) Uani 1 1 d . . .
H7 H 0.7012 0.3605 0.0124 0.038 Uiso 1 1 d R . .
C8 C 1.1271(10) 0.2328(6) -0.0155(5) 0.0432(14) Uani 1 1 d . . .
H8A H 1.2766 0.2364 -0.0140 0.065 Uiso 0.50 1 calc PR . .
H8B H 1.0756 0.2592 -0.0862 0.065 Uiso 0.50 1 calc PR . .
H8C H 1.1156 0.1433 0.0035 0.065 Uiso 0.50 1 calc PR . .
H8D H 1.2371 0.2738 -0.0507 0.065 Uiso 0.50 1 d PR . .
H8E H 1.2292 0.1369 0.0284 0.065 Uiso 0.50 1 d PR . .
H8F H 1.0335 0.2002 -0.0697 0.065 Uiso 0.50 1 d PR . .
C9 C 0.5408(9) 0.1638(6) 0.4070(4) 0.0428(14) Uani 1 1 d . . .
H9A H 0.6220 0.2217 0.4337 0.051 Uiso 1 1 calc R . .
H9B H 0.6029 0.0740 0.4360 0.051 Uiso 1 1 calc R . .
C10 C 0.3158(10) 0.2052(6) 0.4473(5) 0.0456(15) Uani 1 1 d . . .
H10 H 0.2831 0.2102 0.5214 0.055 Uiso 1 1 d R . .
C11 C 0.1496(11) 0.2378(7) 0.3905(6) 0.0593(18) Uani 1 1 d . . .
H11A H 0.0084 0.2637 0.4220 0.071 Uiso 1 1 d R . .
H11B H 0.1695 0.2353 0.3155 0.071 Uiso 1 1 d R . .
O3 O 0.2505(11) 0.9924(5) 0.1744(4) 0.0860(19) Uani 1 1 d . . .
O4 O 0.3763(7) 0.7580(4) 0.1779(3) 0.0506(11) Uani 1 1 d . . .
C12 C 0.1385(10) 0.8591(6) 0.3318(5) 0.0473(16) Uani 1 1 d . . .
F1 F 0.0971(7) 0.9530(4) 0.3977(3) 0.0704(13) Uani 1 1 d . . .
F2 F -0.0394(6) 0.8592(5) 0.2885(4) 0.0863(16) Uani 1 1 d . . .
F3 F 0.1971(9) 0.7450(4) 0.3897(3) 0.0896(17) 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
S1 O2 1.412(5) . ?
S1 O4 1.420(4) . ?
S1 O3 1.457(5) . ?
S1 C12 1.800(6) . ?
O1 C1 1.223(6) . ?
N1 C1 1.368(7) . ?
N1 C7 1.438(7) . ?
N1 C8 1.451(7) . ?
N2 C1 1.359(7) . ?
N2 C3 1.436(7) . ?
N2 C2 1.449(7) . ?
N3 C5 1.349(7) . ?
N3 C4 1.457(7) . ?
N3 C3 1.479(7) . ?
N4 C5 1.333(7) . ?
N4 C6 1.449(7) . ?
N4 C7 1.459(6) . ?
N5 C5 1.322(7) . ?
N5 C9 1.447(7) . ?
N5 H5 0.8800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9930 . ?
C2 H2E 0.8579 . ?
C2 H2F 0.9043 . ?
C3 C7 1.531(8) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9077 . ?
C4 H4E 0.9447 . ?
C4 H4F 0.8981 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9601 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9929 . ?
C8 H8E 1.1874 . ?
C8 H8F 1.0754 . ?
C9 C10 1.485(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.296(9) . ?
C10 H10 0.9600 . ?
C11 H11A 0.9599 . ?
C11 H11B 0.9600 . ?
C12 F2 1.307(8) . ?
C12 F1 1.315(7) . ?
C12 F3 1.352(8) . ?

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 S1 O4 118.9(3) . . ?
O2 S1 O3 111.1(4) . . ?
O4 S1 O3 113.7(3) . . ?
O2 S1 C12 104.6(3) . . ?
O4 S1 C12 104.1(3) . . ?
O3 S1 C12 102.3(3) . . ?
C1 N1 C7 112.4(4) . . ?
C1 N1 C8 123.0(4) . . ?
C7 N1 C8 124.3(4) . . ?
C1 N2 C3 112.2(4) . . ?
C1 N2 C2 123.0(5) . . ?
C3 N2 C2 123.7(5) . . ?
C5 N3 C4 126.2(4) . . ?
C5 N3 C3 109.1(4) . . ?
C4 N3 C3 118.0(4) . . ?
C5 N4 C6 124.8(4) . . ?
C5 N4 C7 111.6(4) . . ?
C6 N4 C7 123.6(4) . . ?
C5 N5 C9 128.1(5) . . ?
C5 N5 H5 115.9 . . ?
C9 N5 H5 115.9 . . ?
O1 C1 N2 125.9(5) . . ?
O1 C1 N1 126.2(5) . . ?
N2 C1 N1 108.0(4) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C2 H2D 114.9 . . ?
H2A C2 H2D 68.9 . . ?
H2B C2 H2D 133.3 . . ?
H2C C2 H2D 41.7 . . ?
N2 C2 H2E 105.4 . . ?
H2A C2 H2E 142.8 . . ?
H2B C2 H2E 44.8 . . ?
H2C C2 H2E 69.3 . . ?
H2D C2 H2E 107.3 . . ?
N2 C2 H2F 103.4 . . ?
H2A C2 H2F 45.3 . . ?
H2B C2 H2F 69.8 . . ?
H2C C2 H2F 144.7 . . ?
H2D C2 H2F 111.8 . . ?
H2E C2 H2F 114.0 . . ?
N2 C3 N3 114.3(4) . . ?
N2 C3 C7 103.9(4) . . ?
N3 C3 C7 104.2(4) . . ?
N2 C3 H3 111.3 . . ?
N3 C3 H3 111.3 . . ?
C7 C3 H3 111.3 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C4 H4D 102.4 . . ?
H4A C4 H4D 51.5 . . ?
H4B C4 H4D 147.4 . . ?
H4C C4 H4D 64.2 . . ?
N3 C4 H4E 110.8 . . ?
H4A C4 H4E 64.8 . . ?
H4B C4 H4E 47.1 . . ?
H4C C4 H4E 138.6 . . ?
H4D C4 H4E 114.8 . . ?
N3 C4 H4F 113.2 . . ?
H4A C4 H4F 136.3 . . ?
H4B C4 H4F 64.5 . . ?
H4C C4 H4F 46.7 . . ?
H4D C4 H4F 108.8 . . ?
H4E C4 H4F 107.0 . . ?
N5 C5 N4 122.2(5) . . ?
N5 C5 N3 125.9(5) . . ?
N4 C5 N3 111.8(4) . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 N4 114.4(4) . . ?
N1 C7 C3 103.1(4) . . ?
N4 C7 C3 102.8(4) . . ?
N1 C7 H7 110.4 . . ?
N4 C7 H7 109.2 . . ?
C3 C7 H7 116.8 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C8 H8D 109.3 . . ?
H8A C8 H8D 36.4 . . ?
H8B C8 H8D 75.9 . . ?
H8C C8 H8D 135.9 . . ?
N1 C8 H8E 111.0 . . ?
H8A C8 H8E 69.5 . . ?
H8B C8 H8E 137.0 . . ?
H8C C8 H8E 42.3 . . ?
H8D C8 H8E 103.4 . . ?
N1 C8 H8F 113.3 . . ?
H8A C8 H8F 135.1 . . ?
H8B C8 H8F 42.7 . . ?
H8C C8 H8F 68.4 . . ?
H8D C8 H8F 113.2 . . ?
H8E C8 H8F 106.2 . . ?
N5 C9 C10 115.1(5) . . ?
N5 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N5 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 125.7(6) . . ?
C11 C10 H10 113.9 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 H11A 121.2 . . ?
C10 C11 H11B 118.9 . . ?
H11A C11 H11B 120.0 . . ?
F2 C12 F1 107.9(5) . . ?
F2 C12 F3 107.0(6) . . ?
F1 C12 F3 106.9(5) . . ?
F2 C12 S1 111.7(5) . . ?
F1 C12 S1 113.4(4) . . ?
F3 C12 S1 109.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.14
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.091
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_ro19
_database_code_depnum_ccdc_archive 'CCDC 1064130'
_audit_update_record             
;
2015-05-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        aza-glycoluril
_chemical_name_common            'N-methyl iminium glycoluril triflate salt '
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H18 N5 O, C F3 O3 S'
_chemical_formula_sum            'C10 H18 F3 N5 O4 S'
_chemical_formula_weight         361.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.56300(10)
_cell_length_b                   14.3405(3)
_cell_length_c                   15.7391(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.2250(10)
_cell_angle_gamma                90
_cell_volume                     1477.29(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    11428
_cell_measurement_theta_min      1.924
_cell_measurement_theta_max      28.311

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '0.5 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            11428
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.924
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3667
_reflns_number_gt                3428
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXTL-2014 (Sheldrick, 2008)'
_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)+(0.0346P)²+0.8082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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 1.06518(18) 0.14965(9) 1.13583(8) 0.0205(2) Uani 1 1 d . . . . .
H1A H 1.2045 0.1259 1.1330 0.031 Uiso 1 1 calc R U . . .
H1B H 0.9986 0.1169 1.1809 0.031 Uiso 1 1 calc R U . . .
H1C H 1.0701 0.2166 1.1484 0.031 Uiso 1 1 calc R U . . .
N2 N 0.95074(14) 0.13438(7) 1.05501(6) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.73052(16) 0.12869(7) 1.04416(7) 0.0119(2) Uani 1 1 d . . . . .
H3 H 0.6766 0.0755 1.0769 0.014 Uiso 1 1 calc R U . . .
N4 N 0.62606(14) 0.21607(7) 1.06114(6) 0.01341(18) Uani 1 1 d . . . . .
C5 C 0.61055(19) 0.24742(8) 1.14864(7) 0.0174(2) Uani 1 1 d . . . . .
H5A H 0.4694 0.2660 1.1564 0.026 Uiso 1 1 calc R U . . .
H5B H 0.7016 0.3008 1.1603 0.026 Uiso 1 1 calc R U . . .
H5C H 0.6502 0.1965 1.1880 0.026 Uiso 1 1 calc R U . . .
C6 C 0.55136(15) 0.25532(7) 0.98823(7) 0.0116(2) Uani 1 1 d . . . . .
N7 N 0.44519(15) 0.33345(7) 0.97913(6) 0.01504(19) Uani 1 1 d . . . . .
H7 H 0.411(2) 0.3486(11) 0.9300(11) 0.022(4) Uiso 1 1 d . . . . .
C8 C 0.3851(2) 0.39802(9) 1.04491(8) 0.0238(3) Uani 1 1 d . . . . .
H8A H 0.5056 0.4151 1.0822 0.036 Uiso 1 1 calc R U . . .
H8B H 0.2841 0.3679 1.0787 0.036 Uiso 1 1 calc R U . . .
H8C H 0.3255 0.4543 1.0179 0.036 Uiso 1 1 calc R U . . .
N9 N 0.59805(14) 0.20498(6) 0.91971(6) 0.01227(18) Uani 1 1 d . . . . .
C10 C 0.48084(17) 0.21359(8) 0.83747(7) 0.0156(2) Uani 1 1 d . . . . .
H10A H 0.5010 0.2760 0.8141 0.023 Uiso 1 1 calc R U . . .
H10B H 0.3355 0.2040 0.8451 0.023 Uiso 1 1 calc R U . . .
H10C H 0.5275 0.1666 0.7981 0.023 Uiso 1 1 calc R U . . .
C11 C 0.68919(16) 0.11521(7) 0.94702(7) 0.0119(2) Uani 1 1 d . . . . .
H11 H 0.5945 0.0618 0.9331 0.014 Uiso 1 1 calc R U . . .
N12 N 0.88956(14) 0.09881(7) 0.91842(6) 0.01497(19) Uani 1 1 d . . . . .
C13 C 0.93086(18) 0.08700(8) 0.83005(7) 0.0182(2) Uani 1 1 d . . . . .
H13A H 0.8279 0.0456 0.8019 0.027 Uiso 1 1 calc R U . . .
H13B H 1.0668 0.0595 0.8268 0.027 Uiso 1 1 calc R U . . .
H13C H 0.9259 0.1478 0.8016 0.027 Uiso 1 1 calc R U . . .
C14 C 1.04109(16) 0.11447(8) 0.98148(7) 0.0136(2) Uani 1 1 d . . . . .
O15 O 1.22534(12) 0.10900(6) 0.97416(6) 0.01902(18) Uani 1 1 d . . . . .
S16 S 1.10024(4) 0.48079(2) 0.80674(2) 0.01293(8) Uani 1 1 d . . . . .
O17 O 1.29477(13) 0.43705(8) 0.83006(6) 0.0289(2) Uani 1 1 d . . . . .
O18 O 1.03693(13) 0.47501(6) 0.71721(5) 0.01932(18) Uani 1 1 d . . . . .
O19 O 1.06910(16) 0.56994(6) 0.84549(6) 0.0281(2) Uani 1 1 d . . . . .
C20 C 0.91986(17) 0.40445(8) 0.85620(7) 0.0161(2) Uani 1 1 d . . . . .
F21 F 0.93530(15) 0.31737(6) 0.82749(6) 0.0385(2) Uani 1 1 d . . . . .
F22 F 0.95284(12) 0.40226(6) 0.94049(5) 0.03002(19) Uani 1 1 d . . . . .
F23 F 0.72823(11) 0.43199(6) 0.83831(5) 0.02620(18) 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 1.4454(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C14 1.3688(14) . ?
N2 C3 1.4451(13) . ?
C3 N4 1.4624(14) . ?
C3 C11 1.5452(15) . ?
C3 H3 1.0000 . ?
N4 C6 1.3382(14) . ?
N4 C5 1.4594(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N7 1.3217(14) . ?
C6 N9 1.3517(14) . ?
N7 C8 1.4646(15) . ?
N7 H7 0.818(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N9 C10 1.4614(13) . ?
N9 C11 1.4703(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N12 1.4403(13) . ?
C11 H11 1.0000 . ?
N12 C14 1.3709(14) . ?
N12 C13 1.4465(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O15 1.2256(13) . ?
S16 O19 1.4375(9) . ?
S16 O18 1.4418(9) . ?
S16 O17 1.4454(9) . ?
S16 C20 1.8282(12) . ?
C20 F23 1.3285(13) . ?
C20 F22 1.3287(14) . ?
C20 F21 1.3345(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 N2 C3 112.34(9) . . ?
C14 N2 C1 123.11(9) . . ?
C3 N2 C1 124.26(9) . . ?
N2 C3 N4 114.09(9) . . ?
N2 C3 C11 103.01(8) . . ?
N4 C3 C11 103.74(8) . . ?
N2 C3 H3 111.8 . . ?
N4 C3 H3 111.8 . . ?
C11 C3 H3 111.8 . . ?
C6 N4 C5 129.27(10) . . ?
C6 N4 C3 110.54(9) . . ?
C5 N4 C3 120.17(9) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N7 C6 N4 127.33(10) . . ?
N7 C6 N9 121.00(10) . . ?
N4 C6 N9 111.67(9) . . ?
C6 N7 C8 128.80(10) . . ?
C6 N7 H7 115.7(11) . . ?
C8 N7 H7 115.5(11) . . ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 N9 C10 121.74(9) . . ?
C6 N9 C11 110.22(9) . . ?
C10 N9 C11 120.61(9) . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N12 C11 N9 114.37(9) . . ?
N12 C11 C3 103.41(8) . . ?
N9 C11 C3 102.58(8) . . ?
N12 C11 H11 111.9 . . ?
N9 C11 H11 111.9 . . ?
C3 C11 H11 111.9 . . ?
C14 N12 C11 112.17(9) . . ?
C14 N12 C13 122.56(10) . . ?
C11 N12 C13 124.04(9) . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O15 C14 N2 125.79(10) . . ?
O15 C14 N12 126.12(11) . . ?
N2 C14 N12 108.06(9) . . ?
O19 S16 O18 115.22(6) . . ?
O19 S16 O17 115.39(7) . . ?
O18 S16 O17 114.13(6) . . ?
O19 S16 C20 103.60(5) . . ?
O18 S16 C20 103.46(5) . . ?
O17 S16 C20 102.68(5) . . ?
F23 C20 F22 107.50(9) . . ?
F23 C20 F21 107.50(10) . . ?
F22 C20 F21 107.77(10) . . ?
F23 C20 S16 111.36(8) . . ?
F22 C20 S16 112.11(8) . . ?
F21 C20 S16 110.39(8) . . ?

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
C14 N2 C3 N4 -119.53(10) . . . . ?
C1 N2 C3 N4 66.56(14) . . . . ?
C14 N2 C3 C11 -7.80(12) . . . . ?
C1 N2 C3 C11 178.29(10) . . . . ?
N2 C3 N4 C6 105.91(10) . . . . ?
C11 C3 N4 C6 -5.39(11) . . . . ?
N2 C3 N4 C5 -75.66(12) . . . . ?
C11 C3 N4 C5 173.04(9) . . . . ?
C5 N4 C6 N7 0.40(19) . . . . ?
C3 N4 C6 N7 178.64(10) . . . . ?
C5 N4 C6 N9 180.00(10) . . . . ?
C3 N4 C6 N9 -1.76(12) . . . . ?
N4 C6 N7 C8 1.33(19) . . . . ?
N9 C6 N7 C8 -178.23(11) . . . . ?
N7 C6 N9 C10 -21.66(15) . . . . ?
N4 C6 N9 C10 158.71(9) . . . . ?
N7 C6 N9 C11 -171.64(9) . . . . ?
N4 C6 N9 C11 8.73(12) . . . . ?
C6 N9 C11 N12 -122.55(10) . . . . ?
C10 N9 C11 N12 87.07(12) . . . . ?
C6 N9 C11 C3 -11.33(11) . . . . ?
C10 N9 C11 C3 -161.70(9) . . . . ?
N2 C3 C11 N12 9.67(11) . . . . ?
N4 C3 C11 N12 128.87(9) . . . . ?
N2 C3 C11 N9 -109.52(9) . . . . ?
N4 C3 C11 N9 9.67(10) . . . . ?
N9 C11 N12 C14 101.66(11) . . . . ?
C3 C11 N12 C14 -9.06(12) . . . . ?
N9 C11 N12 C13 -65.87(14) . . . . ?
C3 C11 N12 C13 -176.59(10) . . . . ?
C3 N2 C14 O15 -175.56(11) . . . . ?
C1 N2 C14 O15 -1.57(19) . . . . ?
C3 N2 C14 N12 2.52(13) . . . . ?
C1 N2 C14 N12 176.51(10) . . . . ?
C11 N12 C14 O15 -177.36(11) . . . . ?
C13 N12 C14 O15 -9.62(18) . . . . ?
C11 N12 C14 N2 4.57(13) . . . . ?
C13 N12 C14 N2 172.31(10) . . . . ?
O19 S16 C20 F23 62.21(10) . . . . ?
O18 S16 C20 F23 -58.37(9) . . . . ?
O17 S16 C20 F23 -177.36(8) . . . . ?
O19 S16 C20 F22 -58.29(10) . . . . ?
O18 S16 C20 F22 -178.87(8) . . . . ?
O17 S16 C20 F22 62.14(10) . . . . ?
O19 S16 C20 F21 -178.45(9) . . . . ?
O18 S16 C20 F21 60.97(10) . . . . ?
O17 S16 C20 F21 -58.02(10) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.050

