# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_uni1504
_database_code_depnum_ccdc_archive 'CCDC 1422710'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 F3 N5 O2, 1.4(H2 O)'
_chemical_formula_sum            'C25 H23.8 F3 N5 O3.4'
_chemical_formula_weight         505.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.8619(3)
_cell_length_b                   10.1495(2)
_cell_length_c                   17.3464(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.9414(13)
_cell_angle_gamma                90
_cell_volume                     2357.98(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5514
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      72.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.959
_shelx_estimated_absorpt_T_min   0.765
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6593
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14514
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.300
_diffrn_reflns_theta_max         72.742
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4601
_reflns_number_gt                3236
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1241P)²+1.7884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     402
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2321
_refine_ls_wR_factor_gt          0.2051
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.058
_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
F1 F 0.29978(16) 0.4603(2) 0.05861(12) 0.0561(6) Uani 1 1 d . . . . .
F2 F 0.05424(19) 0.1307(3) 0.01556(16) 0.0846(9) Uani 1 1 d . . . . .
F3A F -0.0203(4) 0.3952(6) 0.2866(3) 0.1031(18) Uani 0.6 1 d . . P A 1
F3B F 0.0855(6) 0.5225(13) 0.1295(4) 0.153(5) Uani 0.4 1 d . . P A 2
O1 O 0.47929(19) 0.1999(2) 0.30617(13) 0.0460(6) Uani 1 1 d . . . . .
O2 O 0.1364(2) 0.3422(3) -0.04391(17) 0.0733(9) Uani 1 1 d . . . . .
N1 N 0.50741(19) 0.2115(2) 0.55712(16) 0.0394(6) Uani 1 1 d . . . . .
N2 N 0.41956(18) 0.3635(2) 0.47520(13) 0.0300(5) Uani 1 1 d . . . . .
N3 N 0.35888(18) 0.4688(2) 0.44806(14) 0.0308(5) Uani 1 1 d . . . . .
N4 N 0.26532(19) 0.6351(2) 0.47788(14) 0.0338(6) Uani 1 1 d . . . . .
N5 N 0.3869(2) 0.3850(3) 0.30329(15) 0.0375(6) Uani 1 1 d . . . . .
H5N H 0.367(3) 0.439(4) 0.331(2) 0.052(11) Uiso 1 1 d . . . . .
C1 C 0.3284(2) 0.5324(3) 0.50423(16) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.3590(2) 0.4991(3) 0.58702(17) 0.0357(6) Uani 1 1 d . . . . .
H2 H 0.3364 0.5495 0.6251 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4208(2) 0.3947(3) 0.61077(18) 0.0370(7) Uani 1 1 d . . . . .
H3 H 0.4428 0.3719 0.6656 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4515(2) 0.3211(3) 0.55273(17) 0.0329(6) Uani 1 1 d . . . . .
C5 C 0.5105(2) 0.1855(3) 0.48105(19) 0.0378(7) Uani 1 1 d . . . . .
C6 C 0.4569(2) 0.2773(3) 0.42802(18) 0.0340(6) Uani 1 1 d . . . . .
C7 C 0.4415(2) 0.2850(3) 0.34104(18) 0.0355(6) Uani 1 1 d . . . . .
C8 C 0.3713(3) 0.4071(3) 0.21827(17) 0.0396(7) Uani 1 1 d . . . . .
H8A H 0.4330 0.3828 0.2029 0.047 Uiso 1 1 calc R U . . .
H8B H 0.3593 0.5022 0.2071 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2846(2) 0.3297(3) 0.16709(17) 0.0358(7) Uani 1 1 d . . . . .
C10 C 0.2534(3) 0.3601(3) 0.08689(19) 0.0424(7) Uani 1 1 d . . . . .
C11 C 0.1749(3) 0.2973(4) 0.0338(2) 0.0538(9) Uani 1 1 d . . . . .
C12 C 0.1301(3) 0.1949(4) 0.0657(2) 0.0572(10) Uani 1 1 d . . . . .
C13 C 0.1572(3) 0.1618(4) 0.1439(2) 0.0534(9) Uani 1 1 d . . . . .
H13 H 0.1233 0.0935 0.1637 0.064 Uiso 1 1 calc R U . . .
C14 C 0.2361(3) 0.2298(3) 0.1952(2) 0.0454(8) Uani 1 1 d . . . . .
H14 H 0.2564 0.2065 0.2501 0.055 Uiso 1 1 calc R U . . .
C15 C 0.1970(4) 0.3200(4) -0.0949(3) 0.0697(12) Uani 1 1 d . . . . .
H15A H 0.1645 0.3545 -0.1480 0.084 Uiso 1 1 calc R U . . .
H15B H 0.2612 0.3647 -0.0743 0.084 Uiso 1 1 calc R U . . .
H15C H 0.2084 0.2251 -0.0985 0.084 Uiso 1 1 calc R U . . .
C16 C 0.2482(2) 0.6875(3) 0.39732(17) 0.0378(7) Uani 1 1 d D . . . .
H16 H 0.3142 0.6953 0.3844 0.045 Uiso 1 1 calc R U . B 1
C17 C 0.2103(3) 0.8272(3) 0.4074(2) 0.0481(8) Uani 1 1 d . . . . .
H17A H 0.2665 0.8894 0.4260 0.058 Uiso 1 1 calc R U . . .
H17B H 0.1663 0.8601 0.3567 0.058 Uiso 1 1 calc R U . . .
C18 C 0.1524(3) 0.8091(3) 0.4702(2) 0.0471(8) Uani 1 1 d . . . . .
H18A H 0.0863 0.7686 0.4471 0.057 Uiso 1 1 calc R U . . .
H18B H 0.1431 0.8941 0.4954 0.057 Uiso 1 1 calc R U . . .
C19 C 0.2204(3) 0.7165(3) 0.53000(19) 0.0432(8) Uani 1 1 d . . . . .
H19A H 0.2721 0.7662 0.5693 0.052 Uiso 1 1 calc R U . . .
H19B H 0.1816 0.6619 0.5586 0.052 Uiso 1 1 calc R U . . .
C20A C 0.1767(7) 0.6164(11) 0.3288(5) 0.0392(19) Uani 0.6 1 d D . P A 1
C21A C 0.1084(6) 0.5319(8) 0.3415(4) 0.0421(17) Uani 0.6 1 d . . P A 1
H21A H 0.1035 0.5113 0.3938 0.051 Uiso 0.6 1 calc R U P A 1
C22A C 0.0476(5) 0.4782(7) 0.2770(5) 0.0538(16) Uani 0.6 1 d . . P A 1
C23A C 0.0500(6) 0.5044(8) 0.1989(5) 0.0491(17) Uani 0.6 1 d . . P A 1
H23A H 0.0068 0.4605 0.1550 0.059 Uiso 0.6 1 calc R U P A 1
C24A C 0.1185(6) 0.5977(7) 0.1880(4) 0.0573(18) Uani 0.6 1 d . . P A 1
H24A H 0.1198 0.6222 0.1355 0.069 Uiso 0.6 1 calc R U P A 1
C25A C 0.1841(6) 0.6549(7) 0.2520(4) 0.0442(15) Uani 0.6 1 d . . P A 1
H25A H 0.2323 0.7174 0.2453 0.053 Uiso 0.6 1 calc R U P A 1
C20B C 0.1701(7) 0.5890(9) 0.3431(5) 0.064(9) Uani 0.4 1 d DG . P A 2
C21B C 0.1614(6) 0.5934(8) 0.2615(5) 0.051(2) Uani 0.4 1 d G . P A 2
H21B H 0.2019 0.6521 0.2408 0.061 Uiso 0.4 1 calc R U P A 2
C22B C 0.0933(6) 0.5121(10) 0.2102(4) 0.070(5) Uani 0.4 1 d G . P A 2
C23B C 0.0340(5) 0.4263(9) 0.2404(5) 0.071(3) Uani 0.4 1 d G . P A 2
H23B H -0.0126 0.3708 0.2053 0.085 Uiso 0.4 1 calc R U P A 2
C24B C 0.0427(5) 0.4219(7) 0.3220(5) 0.066(3) Uani 0.4 1 d G . P A 2
H24B H 0.0022 0.3632 0.3427 0.080 Uiso 0.4 1 calc R U P A 2
C25B C 0.1108(7) 0.5032(9) 0.3734(4) 0.045(3) Uani 0.4 1 d G . P A 2
H25B H 0.1168 0.5001 0.4292 0.054 Uiso 0.4 1 calc R U P A 2
O1SA O 0.3735(4) -0.0600(5) 0.2970(3) 0.0588(13) Uiso 0.6 1 d D . P C 1
H1SA H 0.413(4) 0.003(4) 0.297(5) 0.088 Uiso 0.6 1 d D U P D 1
H1SB H 0.403(4) -0.119(3) 0.329(2) 0.088 Uiso 0.6 1 d D U P E 1
O1SB O 0.3829(5) -0.0348(7) 0.3282(4) 0.0464(15) Uiso 0.4 1 d D . P F 2
H1SC H 0.421(5) 0.025(6) 0.320(5) 0.070 Uiso 0.4 1 d D U P G 2
H1SD H 0.414(5) -0.081(5) 0.367(3) 0.070 Uiso 0.4 1 d D U P H 2
O2SB O 0.3413(6) 0.7538(9) 0.2265(5) 0.077(2) Uiso 0.4 1 d D . P I 2
H2SA H 0.356(6) 0.824(5) 0.252(5) 0.115 Uiso 0.4 1 d D U P J 2
H2SB H 0.394(3) 0.717(8) 0.222(6) 0.115 Uiso 0.4 1 d D U P K 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 C10 1.361(4) . ?
F2 C12 1.347(4) . ?
F3A C22A 1.305(9) . ?
F3B C22B 1.380(10) . ?
O1 C7 1.245(4) . ?
O2 C15 1.388(5) . ?
O2 C11 1.393(4) . ?
N1 C4 1.346(4) . ?
N1 C5 1.357(4) . ?
N2 N3 1.366(3) . ?
N2 C4 1.372(3) . ?
N2 C6 1.386(4) . ?
N3 C1 1.326(4) . ?
N4 C1 1.362(4) . ?
N4 C16 1.456(4) . ?
N4 C19 1.475(4) . ?
N5 C7 1.333(4) . ?
N5 C8 1.452(4) . ?
C1 C2 1.429(4) . ?
C2 C3 1.358(4) . ?
C3 C4 1.405(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.470(4) . ?
C8 C9 1.516(4) . ?
C9 C14 1.374(4) . ?
C9 C10 1.381(4) . ?
C10 C11 1.386(5) . ?
C11 C12 1.396(6) . ?
C12 C13 1.353(5) . ?
C13 C14 1.402(5) . ?
C16 C20A 1.520(7) . ?
C16 C17 1.538(4) . ?
C16 C20B 1.591(6) . ?
C17 C18 1.521(5) . ?
C18 C19 1.532(5) . ?
C20A C21A 1.337(13) . ?
C20A C25A 1.416(12) . ?
C21A C22A 1.331(10) . ?
C22A C23A 1.389(11) . ?
C23A C24A 1.387(10) . ?
C24A C25A 1.370(10) . ?
C20B C21B 1.3900 . ?
C20B C25B 1.3900 . ?
C21B C22B 1.3900 . ?
C22B C23B 1.3900 . ?
C23B C24B 1.3900 . ?
C24B C25B 1.3900 . ?

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
C15 O2 C11 114.9(3) . . ?
C4 N1 C5 105.5(2) . . ?
N3 N2 C4 126.7(2) . . ?
N3 N2 C6 125.5(2) . . ?
C4 N2 C6 107.8(2) . . ?
C1 N3 N2 114.4(2) . . ?
C1 N4 C16 122.2(2) . . ?
C1 N4 C19 124.0(2) . . ?
C16 N4 C19 113.2(2) . . ?
C7 N5 C8 122.2(3) . . ?
N3 C1 N4 115.2(2) . . ?
N3 C1 C2 123.7(3) . . ?
N4 C1 C2 121.1(3) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 118.8(3) . . ?
N1 C4 N2 110.5(3) . . ?
N1 C4 C3 132.5(3) . . ?
N2 C4 C3 117.0(3) . . ?
N1 C5 C6 111.7(3) . . ?
C5 C6 N2 104.5(3) . . ?
C5 C6 C7 129.0(3) . . ?
N2 C6 C7 126.5(3) . . ?
O1 C7 N5 123.1(3) . . ?
O1 C7 C6 119.6(3) . . ?
N5 C7 C6 117.3(3) . . ?
N5 C8 C9 113.8(3) . . ?
C14 C9 C10 117.9(3) . . ?
C14 C9 C8 124.1(3) . . ?
C10 C9 C8 118.0(3) . . ?
F1 C10 C9 118.4(3) . . ?
F1 C10 C11 117.9(3) . . ?
C9 C10 C11 123.7(3) . . ?
C10 C11 O2 122.1(4) . . ?
C10 C11 C12 115.6(3) . . ?
O2 C11 C12 121.9(4) . . ?
F2 C12 C13 119.7(4) . . ?
F2 C12 C11 117.2(4) . . ?
C13 C12 C11 123.0(3) . . ?
C12 C13 C14 119.0(4) . . ?
C9 C14 C13 120.7(3) . . ?
N4 C16 C20A 119.3(6) . . ?
N4 C16 C17 101.7(2) . . ?
C20A C16 C17 110.7(5) . . ?
N4 C16 C20B 104.8(4) . . ?
C17 C16 C20B 116.5(5) . . ?
C18 C17 C16 103.2(3) . . ?
C17 C18 C19 102.3(3) . . ?
N4 C19 C18 102.2(2) . . ?
C21A C20A C25A 123.9(6) . . ?
C21A C20A C16 121.5(9) . . ?
C25A C20A C16 114.4(9) . . ?
C22A C21A C20A 116.5(7) . . ?
F3A C22A C21A 118.6(7) . . ?
F3A C22A C23A 116.6(7) . . ?
C21A C22A C23A 124.9(7) . . ?
C24A C23A C22A 116.9(7) . . ?
C25A C24A C23A 120.9(6) . . ?
C24A C25A C20A 116.8(7) . . ?
C21B C20B C25B 120.0 . . ?
C21B C20B C16 116.7(5) . . ?
C25B C20B C16 123.3(5) . . ?
C20B C21B C22B 120.0 . . ?
F3B C22B C23B 122.1(8) . . ?
F3B C22B C21B 117.9(8) . . ?
C23B C22B C21B 120.0 . . ?
C24B C23B C22B 120.0 . . ?
C23B C24B C25B 120.0 . . ?
C24B C25B C20B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 N3 C1 -1.1(4) . . . . ?
C6 N2 N3 C1 176.4(3) . . . . ?
N2 N3 C1 N4 -178.1(2) . . . . ?
N2 N3 C1 C2 2.7(4) . . . . ?
C16 N4 C1 N3 -11.5(4) . . . . ?
C19 N4 C1 N3 178.2(3) . . . . ?
C16 N4 C1 C2 167.7(3) . . . . ?
C19 N4 C1 C2 -2.5(4) . . . . ?
N3 C1 C2 C3 -1.8(4) . . . . ?
N4 C1 C2 C3 179.0(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C5 N1 C4 N2 0.2(3) . . . . ?
C5 N1 C4 C3 179.2(3) . . . . ?
N3 N2 C4 N1 177.7(2) . . . . ?
C6 N2 C4 N1 -0.1(3) . . . . ?
N3 N2 C4 C3 -1.5(4) . . . . ?
C6 N2 C4 C3 -179.3(3) . . . . ?
C2 C3 C4 N1 -176.5(3) . . . . ?
C2 C3 C4 N2 2.5(4) . . . . ?
C4 N1 C5 C6 -0.2(3) . . . . ?
N1 C5 C6 N2 0.1(3) . . . . ?
N1 C5 C6 C7 180.0(3) . . . . ?
N3 N2 C6 C5 -177.9(2) . . . . ?
C4 N2 C6 C5 0.0(3) . . . . ?
N3 N2 C6 C7 2.3(4) . . . . ?
C4 N2 C6 C7 -179.8(3) . . . . ?
C8 N5 C7 O1 -3.4(5) . . . . ?
C8 N5 C7 C6 176.5(3) . . . . ?
C5 C6 C7 O1 0.5(5) . . . . ?
N2 C6 C7 O1 -179.6(3) . . . . ?
C5 C6 C7 N5 -179.3(3) . . . . ?
N2 C6 C7 N5 0.5(5) . . . . ?
C7 N5 C8 C9 85.7(4) . . . . ?
N5 C8 C9 C14 -11.6(4) . . . . ?
N5 C8 C9 C10 169.5(3) . . . . ?
C14 C9 C10 F1 179.0(3) . . . . ?
C8 C9 C10 F1 -2.0(4) . . . . ?
C14 C9 C10 C11 1.3(5) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
F1 C10 C11 O2 -6.8(5) . . . . ?
C9 C10 C11 O2 170.9(3) . . . . ?
F1 C10 C11 C12 179.8(3) . . . . ?
C9 C10 C11 C12 -2.6(5) . . . . ?
C15 O2 C11 C10 72.8(5) . . . . ?
C15 O2 C11 C12 -114.1(5) . . . . ?
C10 C11 C12 F2 -179.2(3) . . . . ?
O2 C11 C12 F2 7.3(6) . . . . ?
C10 C11 C12 C13 3.1(6) . . . . ?
O2 C11 C12 C13 -170.4(4) . . . . ?
F2 C12 C13 C14 -179.9(3) . . . . ?
C11 C12 C13 C14 -2.3(6) . . . . ?
C10 C9 C14 C13 -0.4(5) . . . . ?
C8 C9 C14 C13 -179.3(3) . . . . ?
C12 C13 C14 C9 0.8(6) . . . . ?
C1 N4 C16 C20A 79.9(5) . . . . ?
C19 N4 C16 C20A -108.9(5) . . . . ?
C1 N4 C16 C17 -158.1(3) . . . . ?
C19 N4 C16 C17 13.1(3) . . . . ?
C1 N4 C16 C20B 80.2(5) . . . . ?
C19 N4 C16 C20B -108.6(5) . . . . ?
N4 C16 C17 C18 -33.8(3) . . . . ?
C20A C16 C17 C18 94.0(6) . . . . ?
C20B C16 C17 C18 79.5(5) . . . . ?
C16 C17 C18 C19 42.0(3) . . . . ?
C1 N4 C19 C18 -176.4(3) . . . . ?
C16 N4 C19 C18 12.5(4) . . . . ?
C17 C18 C19 N4 -33.1(3) . . . . ?
N4 C16 C20A C21A 19.5(10) . . . . ?
C17 C16 C20A C21A -97.9(9) . . . . ?
N4 C16 C20A C25A -165.0(5) . . . . ?
C17 C16 C20A C25A 77.5(7) . . . . ?
C25A C20A C21A C22A 3.0(12) . . . . ?
C16 C20A C21A C22A 178.0(8) . . . . ?
C20A C21A C22A F3A -179.9(8) . . . . ?
C20A C21A C22A C23A -0.5(12) . . . . ?
F3A C22A C23A C24A 176.7(7) . . . . ?
C21A C22A C23A C24A -2.8(12) . . . . ?
C22A C23A C24A C25A 3.7(11) . . . . ?
C23A C24A C25A C20A -1.4(11) . . . . ?
C21A C20A C25A C24A -2.1(12) . . . . ?
C16 C20A C25A C24A -177.4(7) . . . . ?
N4 C16 C20B C21B -162.6(4) . . . . ?
C17 C16 C20B C21B 85.9(6) . . . . ?
N4 C16 C20B C25B 18.7(6) . . . . ?
C17 C16 C20B C25B -92.8(6) . . . . ?
C25B C20B C21B C22B 0.0 . . . . ?
C16 C20B C21B C22B -178.7(8) . . . . ?
C20B C21B C22B F3B 178.4(8) . . . . ?
C20B C21B C22B C23B 0.0 . . . . ?
F3B C22B C23B C24B -178.3(9) . . . . ?
C21B C22B C23B C24B 0.0 . . . . ?
C22B C23B C24B C25B 0.0 . . . . ?
C23B C24B C25B C20B 0.0 . . . . ?
C21B C20B C25B C24B 0.0 . . . . ?
C16 C20B C25B C24B 178.7(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5N N3 0.82(4) 2.09(4) 2.772(4) 141(4) .
O1SA H1SA O1 0.840(3) 2.19(2) 3.002(6) 163(7) .
O1SA H1SB N1 0.841(3) 2.256(16) 3.056(6) 159(4) 3_656
O1SB H1SC O1 0.840(3) 1.99(3) 2.805(7) 163(8) .
O1SB H1SD N1 0.841(3) 1.985(14) 2.816(7) 169(7) 3_656
O2SB H2SA O1SB 0.840(3) 1.92(2) 2.743(11) 168(10) 1_565
O2SB H2SB O1 0.840(3) 1.95(4) 2.745(9) 157(10) 2_655

_refine_diff_density_max         0.928
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.068

