# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_FTC-bpeta
_database_code_depnum_ccdc_archive 'CCDC 1981473'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
gonzalo-campillo-alvarado@uiowa.edu
elizabeth-keene@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        
'[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[1,2-Bis(4-pyridyl)ethane]'
_chemical_formula_moiety         '2(C8 H10 F N3 O3 S), C12 H12 N2'
_chemical_formula_sum            'C28 H32 F2 N8 O6 S2'
_chemical_formula_weight         678.73
_chemical_absolute_configuration syn
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6333(8)
_cell_length_b                   11.2359(11)
_cell_length_c                   18.1058(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.640(5)
_cell_angle_gamma                90
_cell_volume                     1531.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6823
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.9145
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1097 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9521. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             708
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15295
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.756
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D-8 Venture Duo-Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4924
_reflns_number_total             5271
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0700
_refine_special_details          
'Some reflections were omitted from refinement due to beamstop'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
3. Others
 Sof(C23B)=Sof(H23A)=Sof(H23B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=1-FVAR(1)
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C12(H12), C2(H2), C10(H10), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C1(H1A,H1B), C3(H3C,H3D), C9(H9A,H9B), C23B(H23A,H23B),
 C22B(H22A,H22B), C22A(H22C,H22D), C23A(H23C,H23D)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C24(H24), C21(H21), C20(H20), C17(H17), C18(H18), C27(H27),
 C25(H25), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 1.04810(11) 0.44580(8) 0.69273(4) 0.0468(2) Uani 1 1 d . . . . .
S2 S 0.78327(11) 0.65646(7) -0.17255(4) 0.0462(2) Uani 1 1 d . . . . .
F1 F 0.7420(3) 0.18111(15) 0.36770(10) 0.0503(5) Uani 1 1 d . . . . .
F2 F 0.8234(3) 0.81909(16) 0.11380(10) 0.0575(5) Uani 1 1 d . . . . .
O5 O 0.6948(3) 0.48719(18) -0.09045(10) 0.0388(5) Uani 1 1 d . . . . .
O2 O 0.7914(3) 0.4697(2) 0.57730(10) 0.0437(5) Uani 1 1 d . . . . .
O6 O 0.9303(4) 0.36123(19) 0.06230(12) 0.0543(6) Uani 1 1 d . . . . .
O3 O 1.0027(3) 0.61596(19) 0.42914(11) 0.0531(6) Uani 1 1 d . . . . .
N4 N 0.8865(3) 0.5494(2) 0.01601(12) 0.0320(5) Uani 1 1 d . . . . .
N1 N 0.9218(3) 0.4370(2) 0.47220(11) 0.0330(5) Uani 1 1 d . . . . .
N2 N 0.9172(3) 0.4726(2) 0.34264(12) 0.0386(6) Uani 1 1 d . . . . .
O4 O 0.3847(3) 0.6396(3) -0.15889(15) 0.0626(7) Uani 1 1 d . . . . .
O1 O 0.5387(3) 0.3307(3) 0.64907(16) 0.0598(7) Uani 1 1 d . . . . .
N5 N 0.9107(3) 0.5082(2) 0.14625(12) 0.0382(6) Uani 1 1 d . . . . .
N6 N 0.8892(5) 0.6594(3) 0.22904(15) 0.0510(7) Uani 1 1 d . . . . .
N8 N 0.3766(4) 0.5962(3) -0.00440(15) 0.0517(7) Uani 1 1 d . . . . .
C8 C 0.8516(4) 0.3259(3) 0.45641(15) 0.0352(6) Uani 1 1 d . . . . .
H8 H 0.828894 0.276445 0.494884 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8780(4) 0.5041(3) -0.06008(14) 0.0339(6) Uani 1 1 d . . . . .
H12 H 0.937493 0.426539 -0.057453 0.041 Uiso 1 1 calc R . . . .
N3 N 0.8330(4) 0.3255(3) 0.25632(15) 0.0482(7) Uani 1 1 d . . . . .
N7 N 0.4085(4) 0.3658(3) 0.49441(15) 0.0534(7) Uani 1 1 d . . . . .
C16 C 0.8543(4) 0.6669(3) 0.02858(15) 0.0367(6) Uani 1 1 d . . . . .
H16 H 0.832642 0.720314 -0.011133 0.044 Uiso 1 1 calc R . . . .
C2 C 0.8113(4) 0.4441(3) 0.65531(14) 0.0381(6) Uani 1 1 d . . . . .
H2 H 0.752937 0.506906 0.679822 0.046 Uiso 1 1 calc R . . . .
C7 C 0.8162(4) 0.2893(2) 0.38551(16) 0.0352(6) Uani 1 1 d . . . . .
C10 C 0.6531(4) 0.5237(3) -0.16615(14) 0.0377(6) Uani 1 1 d . . . . .
H10 H 0.693439 0.462008 -0.197674 0.045 Uiso 1 1 calc R . . . .
C5 C 0.9493(4) 0.5148(3) 0.41422(14) 0.0352(6) Uani 1 1 d . . . . .
C11 C 0.9636(4) 0.5854(3) -0.11221(16) 0.0405(7) Uani 1 1 d . . . . .
H11A H 1.034988 0.539193 -0.141326 0.049 Uiso 1 1 calc R . . . .
H11B H 1.039132 0.644275 -0.083375 0.049 Uiso 1 1 calc R . . . .
C6 C 0.8557(4) 0.3633(3) 0.32674(15) 0.0352(6) Uani 1 1 d . . . . .
C4 C 0.9545(4) 0.4794(3) 0.54963(14) 0.0340(6) Uani 1 1 d . . . . .
H4 H 0.989308 0.563426 0.550045 0.041 Uiso 1 1 calc R . . . .
C13 C 0.9106(4) 0.4659(3) 0.07541(14) 0.0358(6) Uani 1 1 d . . . . .
C1 C 0.7247(4) 0.3266(3) 0.66724(17) 0.0433(7) Uani 1 1 d . . . . .
H1A H 0.769115 0.266385 0.636750 0.052 Uiso 1 1 calc R . . . .
H1B H 0.757842 0.303375 0.719293 0.052 Uiso 1 1 calc R . . . .
C3 C 1.0957(4) 0.4105(3) 0.60087(15) 0.0413(7) Uani 1 1 d . . . . .
H3C H 1.213929 0.436638 0.595393 0.050 Uiso 1 1 calc R . . . .
H3D H 1.085208 0.325719 0.591029 0.050 Uiso 1 1 calc R . . . .
C24 C 0.4167(5) 0.4884(3) 0.02510(19) 0.0556(9) Uani 1 1 d . . . . .
H24 H 0.430772 0.426082 -0.007194 0.067 Uiso 1 1 calc R . . . .
C15 C 0.8544(4) 0.7032(3) 0.09806(16) 0.0366(6) Uani 1 1 d . . . . .
C19 C 0.3562(4) 0.4256(3) 0.34222(17) 0.0515(8) Uani 1 1 d . . . . .
C14 C 0.8856(4) 0.6218(3) 0.15894(15) 0.0359(6) Uani 1 1 d . . . . .
C9 C 0.4565(4) 0.5396(4) -0.18947(17) 0.0537(9) Uani 1 1 d . . . . .
H9A H 0.430521 0.545420 -0.243658 0.064 Uiso 1 1 calc R . . . .
H9B H 0.397092 0.469046 -0.175097 0.064 Uiso 1 1 calc R . . . .
C21 C 0.4405(4) 0.4746(3) 0.47128(18) 0.0525(8) Uani 1 1 d . . . . .
H21 H 0.480008 0.531692 0.507418 0.063 Uiso 1 1 calc R . . . .
C20 C 0.4188(5) 0.5082(3) 0.39712(19) 0.0534(9) Uani 1 1 d . . . . .
H20 H 0.445781 0.585311 0.384104 0.064 Uiso 1 1 calc R . . . .
C17 C 0.3468(5) 0.2880(4) 0.4411(2) 0.0550(9) Uani 1 1 d . . . . .
H17 H 0.320975 0.211450 0.455638 0.066 Uiso 1 1 calc R . . . .
C26 C 0.4185(5) 0.5549(4) 0.15031(18) 0.0532(9) Uani 1 1 d . . . . .
C18 C 0.3190(5) 0.3133(3) 0.3663(2) 0.0554(9) Uani 1 1 d . . . . .
H18 H 0.275093 0.254996 0.331610 0.066 Uiso 1 1 calc R . . . .
C27 C 0.3749(5) 0.6650(4) 0.1192(2) 0.0612(9) Uani 1 1 d . . . . .
H27 H 0.357740 0.728689 0.149972 0.073 Uiso 1 1 calc R . . . .
C25 C 0.4382(5) 0.4648(4) 0.1007(2) 0.0591(9) Uani 1 1 d . . . . .
H25 H 0.465944 0.388188 0.118318 0.071 Uiso 1 1 calc R . . . .
C28 C 0.3566(5) 0.6814(4) 0.0439(2) 0.0593(9) Uani 1 1 d . . . . .
H28 H 0.328322 0.757323 0.025153 0.071 Uiso 1 1 calc R . . . .
C23B C 0.461(3) 0.487(2) 0.2315(10) 0.0512(14) Uani 0.238(14) 1 d . . P A 2
H23A H 0.495480 0.405229 0.224384 0.061 Uiso 0.238(14) 1 calc R . P A 2
H23B H 0.557907 0.526391 0.263563 0.061 Uiso 0.238(14) 1 calc R . P A 2
C22B C 0.319(9) 0.489(5) 0.263(3) 0.085(4) Uani 0.238(14) 1 d . . P A 2
H22A H 0.222652 0.448126 0.231202 0.102 Uiso 0.238(14) 1 calc R . P A 2
H22B H 0.283237 0.570336 0.269154 0.102 Uiso 0.238(14) 1 calc R . P A 2
H3A H 0.859(5) 0.374(3) 0.223(2) 0.050(10) Uiso 1 1 d . . . . .
H4A H 0.386(6) 0.632(4) -0.115(3) 0.078(14) Uiso 1 1 d . . . . .
H6A H 0.913(5) 0.605(4) 0.267(2) 0.070(12) Uiso 1 1 d . . . . .
H1 H 0.502(7) 0.346(5) 0.605(3) 0.103(19) Uiso 1 1 d . . . . .
H3B H 0.791(5) 0.255(4) 0.244(2) 0.053(11) Uiso 1 1 d . . . . .
C22A C 0.327(3) 0.4488(11) 0.2593(8) 0.085(4) Uani 0.762(14) 1 d . . P A 1
H22C H 0.203795 0.472080 0.243424 0.102 Uiso 0.762(14) 1 calc R . P A 1
H22D H 0.345509 0.375160 0.233786 0.102 Uiso 0.762(14) 1 calc R . P A 1
C23A C 0.4459(8) 0.5443(7) 0.2348(3) 0.0512(14) Uani 0.762(14) 1 d . . P A 1
H23C H 0.420034 0.620131 0.256197 0.061 Uiso 0.762(14) 1 calc R . P A 1
H23D H 0.569112 0.524812 0.253468 0.061 Uiso 0.762(14) 1 calc R . P A 1
H6B H 0.878(6) 0.729(4) 0.237(2) 0.075(14) Uiso 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 C2 1.821(3) . ?
S1 C3 1.805(3) . ?
S2 C10 1.806(3) . ?
S2 C11 1.795(3) . ?
F1 C7 1.357(3) . ?
F2 C15 1.362(3) . ?
O5 C12 1.427(3) . ?
O5 C10 1.415(3) . ?
O2 C2 1.424(3) . ?
O2 C4 1.422(3) . ?
O6 C13 1.214(4) . ?
O3 C5 1.223(4) . ?
N4 C12 1.460(3) . ?
N4 C16 1.369(4) . ?
N4 C13 1.416(3) . ?
N1 C8 1.369(4) . ?
N1 C5 1.408(3) . ?
N1 C4 1.462(3) . ?
N2 C5 1.363(3) . ?
N2 C6 1.329(4) . ?
O4 C9 1.404(5) . ?
O4 H4A 0.80(5) . ?
O1 C1 1.403(4) . ?
O1 H1 0.82(5) . ?
N5 C13 1.368(3) . ?
N5 C14 1.317(4) . ?
N6 C14 1.334(4) . ?
N6 H6A 0.91(4) . ?
N6 H6B 0.81(5) . ?
N8 C24 1.338(5) . ?
N8 C28 1.323(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.332(4) . ?
C12 H12 0.9800 . ?
C12 C11 1.537(4) . ?
N3 C6 1.327(4) . ?
N3 H3A 0.87(4) . ?
N3 H3B 0.87(4) . ?
N7 C21 1.328(5) . ?
N7 C17 1.329(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.323(4) . ?
C2 H2 0.9800 . ?
C2 C1 1.507(4) . ?
C7 C6 1.422(4) . ?
C10 H10 0.9800 . ?
C10 C9 1.500(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4 0.9800 . ?
C4 C3 1.512(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C24 H24 0.9300 . ?
C24 C25 1.377(5) . ?
C15 C14 1.422(4) . ?
C19 C20 1.385(5) . ?
C19 C18 1.380(5) . ?
C19 C22B 1.58(6) . ?
C19 C22A 1.503(15) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 H21 0.9300 . ?
C21 C20 1.378(5) . ?
C20 H20 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.366(5) . ?
C26 C27 1.376(5) . ?
C26 C25 1.378(5) . ?
C26 C23B 1.641(19) . ?
C26 C23A 1.513(6) . ?
C18 H18 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.360(5) . ?
C25 H25 0.9300 . ?
C28 H28 0.9300 . ?
C23B H23A 0.9700 . ?
C23B H23B 0.9700 . ?
C23B C22B 1.30(7) . ?
C22B H22A 0.9700 . ?
C22B H22B 0.9700 . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.520(15) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?

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
C3 S1 C2 89.72(13) . . ?
C11 S2 C10 88.17(14) . . ?
C10 O5 C12 112.4(2) . . ?
C4 O2 C2 114.2(2) . . ?
C16 N4 C12 120.8(2) . . ?
C16 N4 C13 121.1(2) . . ?
C13 N4 C12 117.7(2) . . ?
C8 N1 C5 120.8(2) . . ?
C8 N1 C4 119.7(2) . . ?
C5 N1 C4 119.3(2) . . ?
C6 N2 C5 121.9(2) . . ?
C9 O4 H4A 111(3) . . ?
C1 O1 H1 114(4) . . ?
C14 N5 C13 121.6(2) . . ?
C14 N6 H6A 118(3) . . ?
C14 N6 H6B 120(3) . . ?
H6A N6 H6B 123(4) . . ?
C28 N8 C24 115.8(3) . . ?
N1 C8 H8 120.3 . . ?
C7 C8 N1 119.5(3) . . ?
C7 C8 H8 120.3 . . ?
O5 C12 N4 107.2(2) . . ?
O5 C12 H12 108.5 . . ?
O5 C12 C11 109.4(2) . . ?
N4 C12 H12 108.5 . . ?
N4 C12 C11 114.6(2) . . ?
C11 C12 H12 108.5 . . ?
C6 N3 H3A 118(2) . . ?
C6 N3 H3B 122(2) . . ?
H3A N3 H3B 120(3) . . ?
C21 N7 C17 116.0(3) . . ?
N4 C16 H16 120.5 . . ?
C15 C16 N4 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
S1 C2 H2 108.8 . . ?
O2 C2 S1 107.54(18) . . ?
O2 C2 H2 108.8 . . ?
O2 C2 C1 110.0(2) . . ?
C1 C2 S1 112.8(2) . . ?
C1 C2 H2 108.8 . . ?
F1 C7 C6 118.6(2) . . ?
C8 C7 F1 121.0(3) . . ?
C8 C7 C6 120.4(3) . . ?
S2 C10 H10 108.5 . . ?
O5 C10 S2 105.36(18) . . ?
O5 C10 H10 108.5 . . ?
O5 C10 C9 111.0(2) . . ?
C9 C10 S2 114.8(2) . . ?
C9 C10 H10 108.5 . . ?
O3 C5 N1 119.9(2) . . ?
O3 C5 N2 122.2(3) . . ?
N2 C5 N1 117.9(3) . . ?
S2 C11 H11A 110.5 . . ?
S2 C11 H11B 110.5 . . ?
C12 C11 S2 106.05(19) . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N2 C6 C7 119.3(2) . . ?
N3 C6 N2 119.3(3) . . ?
N3 C6 C7 121.4(3) . . ?
O2 C4 N1 107.1(2) . . ?
O2 C4 H4 108.9 . . ?
O2 C4 C3 108.7(2) . . ?
N1 C4 H4 108.9 . . ?
N1 C4 C3 114.2(2) . . ?
C3 C4 H4 108.9 . . ?
O6 C13 N4 119.9(2) . . ?
O6 C13 N5 122.6(3) . . ?
N5 C13 N4 117.5(3) . . ?
O1 C1 C2 112.9(3) . . ?
O1 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
S1 C3 H3C 111.2 . . ?
S1 C3 H3D 111.2 . . ?
C4 C3 S1 102.7(2) . . ?
C4 C3 H3C 111.2 . . ?
C4 C3 H3D 111.2 . . ?
H3C C3 H3D 109.1 . . ?
N8 C24 H24 118.2 . . ?
N8 C24 C25 123.5(3) . . ?
C25 C24 H24 118.2 . . ?
F2 C15 C14 117.7(2) . . ?
C16 C15 F2 121.5(3) . . ?
C16 C15 C14 120.8(3) . . ?
C20 C19 C22B 109.8(17) . . ?
C20 C19 C22A 125.2(5) . . ?
C18 C19 C20 116.8(3) . . ?
C18 C19 C22B 132.9(17) . . ?
C18 C19 C22A 118.0(5) . . ?
N5 C14 N6 119.5(3) . . ?
N5 C14 C15 119.9(2) . . ?
N6 C14 C15 120.5(3) . . ?
O4 C9 C10 115.0(3) . . ?
O4 C9 H9A 108.5 . . ?
O4 C9 H9B 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N7 C21 H21 117.9 . . ?
N7 C21 C20 124.1(3) . . ?
C20 C21 H21 117.9 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20 120.4 . . ?
N7 C17 H17 117.9 . . ?
N7 C17 C18 124.1(4) . . ?
C18 C17 H17 117.9 . . ?
C27 C26 C25 116.0(3) . . ?
C27 C26 C23B 141.5(9) . . ?
C27 C26 C23A 117.9(4) . . ?
C25 C26 C23B 102.4(9) . . ?
C25 C26 C23A 126.1(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(4) . . ?
C28 C27 H27 119.7 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
N8 C28 C27 124.1(4) . . ?
N8 C28 H28 118.0 . . ?
C27 C28 H28 118.0 . . ?
C26 C23B H23A 109.8 . . ?
C26 C23B H23B 109.8 . . ?
H23A C23B H23B 108.2 . . ?
C22B C23B C26 110(3) . . ?
C22B C23B H23A 109.8 . . ?
C22B C23B H23B 109.8 . . ?
C19 C22B H22A 109.5 . . ?
C19 C22B H22B 109.5 . . ?
C23B C22B C19 111(5) . . ?
C23B C22B H22A 109.5 . . ?
C23B C22B H22B 109.5 . . ?
H22A C22B H22B 108.1 . . ?
C19 C22A H22C 108.6 . . ?
C19 C22A H22D 108.6 . . ?
C19 C22A C23A 114.6(9) . . ?
H22C C22A H22D 107.6 . . ?
C23A C22A H22C 108.6 . . ?
C23A C22A H22D 108.6 . . ?
C26 C23A C22A 111.3(7) . . ?
C26 C23A H23C 109.4 . . ?
C26 C23A H23D 109.4 . . ?
C22A C23A H23C 109.4 . . ?
C22A C23A H23D 109.4 . . ?
H23C C23A H23D 108.0 . . ?

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
S1 C2 C1 O1 170.8(2) . . . . ?
S2 C10 C9 O4 -47.4(3) . . . . ?
F1 C7 C6 N2 175.5(3) . . . . ?
F1 C7 C6 N3 -4.7(4) . . . . ?
F2 C15 C14 N5 177.9(3) . . . . ?
F2 C15 C14 N6 -1.9(4) . . . . ?
O5 C12 C11 S2 16.3(3) . . . . ?
O5 C10 C9 O4 72.0(4) . . . . ?
O2 C2 C1 O1 -69.1(3) . . . . ?
O2 C4 C3 S1 -40.6(3) . . . . ?
N4 C12 C11 S2 -104.1(2) . . . . ?
N4 C16 C15 F2 179.9(3) . . . . ?
N4 C16 C15 C14 -0.7(4) . . . . ?
N1 C8 C7 F1 -178.1(3) . . . . ?
N1 C8 C7 C6 1.9(4) . . . . ?
N1 C4 C3 S1 -160.13(19) . . . . ?
N8 C24 C25 C26 -0.1(6) . . . . ?
C8 N1 C5 O3 175.9(3) . . . . ?
C8 N1 C5 N2 -5.1(4) . . . . ?
C8 N1 C4 O2 -54.9(3) . . . . ?
C8 N1 C4 C3 65.5(3) . . . . ?
C8 C7 C6 N2 -4.5(4) . . . . ?
C8 C7 C6 N3 175.3(3) . . . . ?
C12 O5 C10 S2 -38.2(3) . . . . ?
C12 O5 C10 C9 -163.1(3) . . . . ?
C12 N4 C16 C15 176.6(3) . . . . ?
C12 N4 C13 O6 2.9(4) . . . . ?
C12 N4 C13 N5 -177.2(2) . . . . ?
N7 C21 C20 C19 1.5(5) . . . . ?
N7 C17 C18 C19 0.2(6) . . . . ?
C16 N4 C12 O5 -79.4(3) . . . . ?
C16 N4 C12 C11 42.3(4) . . . . ?
C16 N4 C13 O6 176.4(3) . . . . ?
C16 N4 C13 N5 -3.7(4) . . . . ?
C16 C15 C14 N5 -1.6(4) . . . . ?
C16 C15 C14 N6 178.6(3) . . . . ?
C2 S1 C3 C4 36.7(2) . . . . ?
C2 O2 C4 N1 147.7(2) . . . . ?
C2 O2 C4 C3 23.8(3) . . . . ?
C10 S2 C11 C12 -31.7(2) . . . . ?
C10 O5 C12 N4 139.1(2) . . . . ?
C10 O5 C12 C11 14.3(3) . . . . ?
C5 N1 C8 C7 2.9(4) . . . . ?
C5 N1 C4 O2 119.9(3) . . . . ?
C5 N1 C4 C3 -119.7(3) . . . . ?
C5 N2 C6 N3 -177.6(3) . . . . ?
C5 N2 C6 C7 2.2(4) . . . . ?
C11 S2 C10 O5 40.3(2) . . . . ?
C11 S2 C10 C9 162.8(2) . . . . ?
C6 N2 C5 O3 -178.6(3) . . . . ?
C6 N2 C5 N1 2.4(4) . . . . ?
C4 O2 C2 S1 4.8(3) . . . . ?
C4 O2 C2 C1 -118.5(3) . . . . ?
C4 N1 C8 C7 177.6(3) . . . . ?
C4 N1 C5 O3 1.2(4) . . . . ?
C4 N1 C5 N2 -179.8(2) . . . . ?
C13 N4 C12 O5 94.1(3) . . . . ?
C13 N4 C12 C11 -144.2(2) . . . . ?
C13 N4 C16 C15 3.3(4) . . . . ?
C13 N5 C14 N6 -179.1(3) . . . . ?
C13 N5 C14 C15 1.1(4) . . . . ?
C3 S1 C2 O2 -25.1(2) . . . . ?
C3 S1 C2 C1 96.4(2) . . . . ?
C24 N8 C28 C27 0.2(6) . . . . ?
C19 C22A C23A C26 175.3(9) . . . . ?
C14 N5 C13 O6 -178.6(3) . . . . ?
C14 N5 C13 N4 1.5(4) . . . . ?
C21 N7 C17 C18 1.2(5) . . . . ?
C20 C19 C18 C17 -0.9(5) . . . . ?
C20 C19 C22B C23B 90(4) . . . . ?
C20 C19 C22A C23A 28.1(19) . . . . ?
C17 N7 C21 C20 -2.1(5) . . . . ?
C26 C27 C28 N8 0.7(6) . . . . ?
C26 C23B C22B C19 -179.0(19) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C18 C19 C22B C23B -99(4) . . . . ?
C18 C19 C22A C23A -151.7(9) . . . . ?
C27 C26 C25 C24 0.9(5) . . . . ?
C27 C26 C23B C22B 64(3) . . . . ?
C27 C26 C23A C22A 124.7(10) . . . . ?
C25 C26 C27 C28 -1.2(6) . . . . ?
C25 C26 C23B C22B -117(3) . . . . ?
C25 C26 C23A C22A -57.4(11) . . . . ?
C28 N8 C24 C25 -0.5(5) . . . . ?
C23B C26 C27 C28 178.0(12) . . . . ?
C23B C26 C25 C24 -178.6(8) . . . . ?
C22B C19 C20 C21 173(3) . . . . ?
C22B C19 C18 C17 -171(4) . . . . ?
C22A C19 C20 C21 -179.7(10) . . . . ?
C22A C19 C18 C17 178.9(10) . . . . ?
C23A C26 C27 C28 177.0(4) . . . . ?
C23A C26 C25 C24 -177.1(4) . . . . ?

_olex2_submission_original_sample_id EMT-bpeta
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_FTC-bpe
_database_code_depnum_ccdc_archive 'CCDC 1981474'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
gonzalo-campillo-alvarado@uiowa.edu
elizabeth-keene@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        
'[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[1,2-Bis(4-pyridyl)ethylene]'
_chemical_formula_moiety         '2(C8 H10 F N3 O3 S), C12 H10 N2'
_chemical_formula_sum            'C28 H30 F2 N8 O6 S2'
_chemical_formula_weight         676.72
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4883(7)
_cell_length_b                   11.2957(11)
_cell_length_c                   18.1735(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.406(5)
_cell_angle_gamma                90
_cell_volume                     1511.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7248
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.906
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0625 before and 0.0397 after correction. The Ratio of minimum to maximum transmission is 0.9564. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12872
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         2.766
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker D-8 Venture Duo-Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_full    0.759
_reflns_Friedel_fraction_max     0.660
_reflns_number_gt                5525
_reflns_number_total             6094
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6094
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.4239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          
'Some reflections were omitted from refinement due to beamstop'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12), C2(H2), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3C,H3D), C11(H11A,H11B), C1(H1A,H1B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C18(H18), C24(H24), C27(H27), C20(H20), C17(H17), C25(H25),
 C22(H22), C28(H28), C23(H23), C21(H21)
2.d X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N3(H3A,H3B)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 1.04465(11) 0.44483(9) 0.69432(4) 0.0451(2) Uani 1 1 d . . . . .
S2 S 0.79010(11) 0.65505(8) -0.17153(5) 0.0455(2) Uani 1 1 d . . . . .
F2 F 0.8332(3) 0.81660(17) 0.11576(11) 0.0567(6) Uani 1 1 d . . . . .
F1 F 0.7438(3) 0.18314(17) 0.36711(11) 0.0518(5) Uani 1 1 d . . . . .
O5 O 0.6946(3) 0.4903(2) -0.08906(11) 0.0386(5) Uani 1 1 d . . . . .
O3 O 0.9986(4) 0.6178(2) 0.43267(12) 0.0532(6) Uani 1 1 d . . . . .
O2 O 0.7820(3) 0.4669(2) 0.57762(10) 0.0441(6) Uani 1 1 d . . . . .
O1 O 0.5273(3) 0.3240(3) 0.64734(14) 0.0575(7) Uani 1 1 d . . . . .
H1 H 0.497534 0.329341 0.601768 0.086 Uiso 1 1 calc GR . . . .
O6 O 0.9331(4) 0.3611(2) 0.06349(13) 0.0541(6) Uani 1 1 d . . . . .
N1 N 0.9171(3) 0.4384(2) 0.47369(11) 0.0319(5) Uani 1 1 d . . . . .
N5 N 0.9158(3) 0.5066(2) 0.14758(13) 0.0373(6) Uani 1 1 d . . . . .
N4 N 0.8947(3) 0.5491(2) 0.01780(12) 0.0311(5) Uani 1 1 d . . . . .
N2 N 0.9147(4) 0.4761(2) 0.34523(12) 0.0382(6) Uani 1 1 d . . . . .
O4 O 0.3852(3) 0.6456(3) -0.15916(14) 0.0612(7) Uani 1 1 d . . . . .
H4A H 0.395971 0.639108 -0.113628 0.092 Uiso 1 1 calc GR . . . .
N6 N 0.8941(4) 0.6561(3) 0.23029(14) 0.0512(7) Uani 1 1 d . . . . .
H6A H 0.911540 0.606199 0.266605 0.061 Uiso 1 1 calc R . . . .
H6B H 0.878267 0.729849 0.239038 0.061 Uiso 1 1 calc R . . . .
C7 C 0.8147(4) 0.2914(3) 0.38569(16) 0.0346(6) Uani 1 1 d . . . . .
N3 N 0.8308(4) 0.3309(3) 0.25747(14) 0.0491(7) Uani 1 1 d . . . . .
H3A H 0.855131 0.377622 0.223248 0.059 Uiso 1 1 calc R . . . .
H3B H 0.791522 0.260513 0.245996 0.059 Uiso 1 1 calc R . . . .
N8 N 0.3862(4) 0.6089(3) -0.00350(16) 0.0484(7) Uani 1 1 d . . . . .
C5 C 0.9457(4) 0.5168(3) 0.41667(15) 0.0342(6) Uani 1 1 d . . . . .
N7 N 0.3942(4) 0.3690(3) 0.49206(16) 0.0518(7) Uani 1 1 d . . . . .
C8 C 0.8492(4) 0.3268(3) 0.45692(15) 0.0339(6) Uani 1 1 d . . . . .
H8 H 0.827419 0.276386 0.494789 0.041 Uiso 1 1 calc R . . . .
C16 C 0.8641(4) 0.6661(3) 0.03080(16) 0.0350(6) Uani 1 1 d . . . . .
H16 H 0.844355 0.719944 -0.008554 0.042 Uiso 1 1 calc R . . . .
C10 C 0.6537(4) 0.5253(3) -0.16485(15) 0.0360(6) Uani 1 1 d . . . . .
H10 H 0.692520 0.462439 -0.195651 0.043 Uiso 1 1 calc R . . . .
C13 C 0.9153(4) 0.4658(3) 0.07680(15) 0.0349(6) Uani 1 1 d . . . . .
C6 C 0.8541(4) 0.3675(3) 0.32829(15) 0.0345(6) Uani 1 1 d . . . . .
C12 C 0.8832(4) 0.5041(3) -0.05837(15) 0.0326(6) Uani 1 1 d . . . . .
H12 H 0.941424 0.426156 -0.055948 0.039 Uiso 1 1 calc R . . . .
C15 C 0.8630(4) 0.7017(3) 0.10021(16) 0.0364(6) Uani 1 1 d . . . . .
C2 C 0.8027(4) 0.4405(3) 0.65537(14) 0.0370(6) Uani 1 1 d . . . . .
H2 H 0.741272 0.502004 0.679567 0.044 Uiso 1 1 calc R . . . .
C3 C 1.0942(4) 0.4115(3) 0.60293(15) 0.0390(7) Uani 1 1 d . . . . .
H3C H 1.214587 0.438628 0.598351 0.047 Uiso 1 1 calc R . . . .
H3D H 1.085046 0.327245 0.592703 0.047 Uiso 1 1 calc R . . . .
C19 C 0.3762(4) 0.4240(3) 0.34064(18) 0.0456(8) Uani 1 1 d . . . . .
C4 C 0.9488(4) 0.4796(3) 0.55118(14) 0.0324(6) Uani 1 1 d . . . . .
H4 H 0.982188 0.563561 0.552385 0.039 Uiso 1 1 calc R . . . .
C18 C 0.3313(5) 0.3127(4) 0.3635(2) 0.0539(9) Uani 1 1 d . . . . .
H18 H 0.293490 0.253979 0.328294 0.065 Uiso 1 1 calc R . . . .
C11 C 0.9727(4) 0.5846(3) -0.10930(17) 0.0388(7) Uani 1 1 d . . . . .
H11A H 1.046772 0.538389 -0.137302 0.047 Uiso 1 1 calc R . . . .
H11B H 1.049115 0.643252 -0.079903 0.047 Uiso 1 1 calc R . . . .
C14 C 0.8915(4) 0.6194(3) 0.16068(15) 0.0356(6) Uani 1 1 d . . . . .
C1 C 0.7177(4) 0.3224(3) 0.66682(18) 0.0430(7) Uani 1 1 d . . . . .
H1A H 0.765232 0.263181 0.636884 0.052 Uiso 1 1 calc R . . . .
H1B H 0.751819 0.299646 0.718926 0.052 Uiso 1 1 calc R . . . .
C26 C 0.4039(4) 0.5652(3) 0.15001(19) 0.0451(8) Uani 1 1 d . . . . .
C24 C 0.4042(5) 0.4997(4) 0.0251(2) 0.0553(9) Uani 1 1 d . . . . .
H24 H 0.410711 0.437179 -0.007572 0.066 Uiso 1 1 calc R . . . .
C27 C 0.3888(5) 0.6782(4) 0.1204(2) 0.0534(9) Uani 1 1 d . . . . .
H27 H 0.386382 0.742891 0.151895 0.064 Uiso 1 1 calc R . . . .
C20 C 0.4265(5) 0.5080(3) 0.39609(18) 0.0481(8) Uani 1 1 d . . . . .
H20 H 0.456639 0.584319 0.383582 0.058 Uiso 1 1 calc R . . . .
C17 C 0.3426(5) 0.2892(4) 0.4382(2) 0.0551(9) Uani 1 1 d . . . . .
H17 H 0.312702 0.213579 0.452075 0.066 Uiso 1 1 calc R . . . .
C25 C 0.4136(5) 0.4735(3) 0.0994(2) 0.0534(9) Uani 1 1 d . . . . .
H25 H 0.426318 0.395531 0.115887 0.064 Uiso 1 1 calc R . . . .
C22 C 0.3698(5) 0.4472(4) 0.26037(19) 0.0558(9) Uani 1 1 d . . . . .
H22 H 0.330390 0.385406 0.227606 0.067 Uiso 1 1 calc R . . . .
C28 C 0.3772(5) 0.6958(4) 0.0453(2) 0.0537(9) Uani 1 1 d . . . . .
H28 H 0.362256 0.772866 0.027260 0.064 Uiso 1 1 calc R . . . .
C9 C 0.4536(5) 0.5435(4) -0.18848(19) 0.0537(9) Uani 1 1 d . . . . .
H9A H 0.425772 0.547651 -0.242659 0.064 Uiso 1 1 calc R . . . .
H9B H 0.391079 0.474993 -0.173275 0.064 Uiso 1 1 calc R . . . .
C23 C 0.4139(5) 0.5460(4) 0.2306(2) 0.0503(8) Uani 1 1 d . . . . .
H23 H 0.454288 0.608394 0.262724 0.060 Uiso 1 1 calc R . . . .
C21 C 0.4316(5) 0.4777(4) 0.4697(2) 0.0531(9) Uani 1 1 d . . . . .
H21 H 0.462759 0.535880 0.505969 0.064 Uiso 1 1 calc R . . . .


_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 C2 1.823(3) . ?
S1 C3 1.806(3) . ?
S2 C10 1.803(3) . ?
S2 C11 1.795(3) . ?
F2 C15 1.356(4) . ?
F1 C7 1.351(4) . ?
O5 C10 1.412(3) . ?
O5 C12 1.430(3) . ?
O3 C5 1.225(4) . ?
O2 C2 1.425(3) . ?
O2 C4 1.425(3) . ?
O1 H1 0.8200 . ?
O1 C1 1.406(4) . ?
O6 C13 1.219(4) . ?
N1 C5 1.409(4) . ?
N1 C8 1.373(4) . ?
N1 C4 1.461(3) . ?
N5 C13 1.366(4) . ?
N5 C14 1.315(4) . ?
N4 C16 1.370(4) . ?
N4 C13 1.414(4) . ?
N4 C12 1.462(3) . ?
N2 C5 1.357(4) . ?
N2 C6 1.325(4) . ?
O4 H4A 0.8200 . ?
O4 C9 1.406(5) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C14 1.328(4) . ?
C7 C8 1.335(4) . ?
C7 C6 1.423(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C6 1.333(4) . ?
N8 C24 1.336(5) . ?
N8 C28 1.333(5) . ?
N7 C17 1.336(5) . ?
N7 C21 1.338(5) . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.325(4) . ?
C10 H10 0.9800 . ?
C10 C9 1.496(5) . ?
C12 H12 0.9800 . ?
C12 C11 1.536(4) . ?
C15 C14 1.426(4) . ?
C2 H2 0.9800 . ?
C2 C1 1.508(5) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C3 C4 1.514(4) . ?
C19 C18 1.385(5) . ?
C19 C20 1.385(5) . ?
C19 C22 1.474(5) . ?
C4 H4 0.9800 . ?
C18 H18 0.9300 . ?
C18 C17 1.369(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C26 C27 1.382(5) . ?
C26 C25 1.395(5) . ?
C26 C23 1.470(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.371(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.366(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(5) . ?
C17 H17 0.9300 . ?
C25 H25 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.308(5) . ?
C28 H28 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C23 H23 0.9300 . ?
C21 H21 0.9300 . ?

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
C3 S1 C2 89.55(13) . . ?
C11 S2 C10 88.49(15) . . ?
C10 O5 C12 112.0(2) . . ?
C4 O2 C2 114.2(2) . . ?
C1 O1 H1 109.5 . . ?
C5 N1 C4 119.3(2) . . ?
C8 N1 C5 120.9(2) . . ?
C8 N1 C4 119.7(2) . . ?
C14 N5 C13 121.4(3) . . ?
C16 N4 C13 120.7(2) . . ?
C16 N4 C12 121.0(2) . . ?
C13 N4 C12 117.8(2) . . ?
C6 N2 C5 121.9(2) . . ?
C9 O4 H4A 109.5 . . ?
H6A N6 H6B 120.0 . . ?
C14 N6 H6A 120.0 . . ?
C14 N6 H6B 120.0 . . ?
F1 C7 C6 119.2(3) . . ?
C8 C7 F1 120.8(3) . . ?
C8 C7 C6 120.0(3) . . ?
H3A N3 H3B 120.0 . . ?
C6 N3 H3A 120.0 . . ?
C6 N3 H3B 120.0 . . ?
C28 N8 C24 115.7(3) . . ?
O3 C5 N1 119.7(3) . . ?
O3 C5 N2 122.3(3) . . ?
N2 C5 N1 117.9(3) . . ?
C17 N7 C21 116.4(3) . . ?
N1 C8 H8 120.3 . . ?
C7 C8 N1 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
N4 C16 H16 120.4 . . ?
C15 C16 N4 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
S2 C10 H10 108.7 . . ?
O5 C10 S2 105.50(19) . . ?
O5 C10 H10 108.7 . . ?
O5 C10 C9 110.4(2) . . ?
C9 C10 S2 114.8(3) . . ?
C9 C10 H10 108.7 . . ?
O6 C13 N5 122.2(3) . . ?
O6 C13 N4 119.7(3) . . ?
N5 C13 N4 118.1(3) . . ?
N2 C6 C7 119.8(3) . . ?
N2 C6 N3 119.4(3) . . ?
N3 C6 C7 120.8(3) . . ?
O5 C12 N4 107.0(2) . . ?
O5 C12 H12 108.7 . . ?
O5 C12 C11 109.7(2) . . ?
N4 C12 H12 108.7 . . ?
N4 C12 C11 114.0(3) . . ?
C11 C12 H12 108.7 . . ?
F2 C15 C14 118.1(3) . . ?
C16 C15 F2 121.2(3) . . ?
C16 C15 C14 120.7(3) . . ?
S1 C2 H2 108.7 . . ?
O2 C2 S1 107.58(18) . . ?
O2 C2 H2 108.7 . . ?
O2 C2 C1 110.4(3) . . ?
C1 C2 S1 112.6(2) . . ?
C1 C2 H2 108.7 . . ?
S1 C3 H3C 111.2 . . ?
S1 C3 H3D 111.2 . . ?
H3C C3 H3D 109.1 . . ?
C4 C3 S1 102.8(2) . . ?
C4 C3 H3C 111.2 . . ?
C4 C3 H3D 111.2 . . ?
C18 C19 C20 116.9(3) . . ?
C18 C19 C22 119.5(3) . . ?
C20 C19 C22 123.7(3) . . ?
O2 C4 N1 107.0(2) . . ?
O2 C4 C3 108.4(2) . . ?
O2 C4 H4 109.0 . . ?
N1 C4 C3 114.3(2) . . ?
N1 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.0 . . ?
S2 C11 H11A 110.5 . . ?
S2 C11 H11B 110.5 . . ?
C12 C11 S2 106.0(2) . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N5 C14 N6 119.8(3) . . ?
N5 C14 C15 119.9(3) . . ?
N6 C14 C15 120.3(3) . . ?
O1 C1 C2 112.9(3) . . ?
O1 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C27 C26 C25 116.1(3) . . ?
C27 C26 C23 120.7(3) . . ?
C25 C26 C23 123.2(4) . . ?
N8 C24 H24 117.8 . . ?
N8 C24 C25 124.5(4) . . ?
C25 C24 H24 117.8 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(4) . . ?
C28 C27 H27 119.7 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
N7 C17 C18 123.6(4) . . ?
N7 C17 H17 118.2 . . ?
C18 C17 H17 118.2 . . ?
C26 C25 H25 120.4 . . ?
C24 C25 C26 119.3(4) . . ?
C24 C25 H25 120.4 . . ?
C19 C22 H22 116.8 . . ?
C23 C22 C19 126.5(4) . . ?
C23 C22 H22 116.8 . . ?
N8 C28 C27 123.8(4) . . ?
N8 C28 H28 118.1 . . ?
C27 C28 H28 118.1 . . ?
O4 C9 C10 114.7(3) . . ?
O4 C9 H9A 108.6 . . ?
O4 C9 H9B 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C26 C23 H23 117.7 . . ?
C22 C23 C26 124.5(4) . . ?
C22 C23 H23 117.7 . . ?
N7 C21 C20 123.6(4) . . ?
N7 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?

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
S1 C2 C1 O1 170.9(2) . . . . ?
S1 C3 C4 O2 -41.1(3) . . . . ?
S1 C3 C4 N1 -160.3(2) . . . . ?
S2 C10 C9 O4 -46.5(3) . . . . ?
F2 C15 C14 N5 178.1(3) . . . . ?
F2 C15 C14 N6 -2.0(4) . . . . ?
F1 C7 C8 N1 -178.4(3) . . . . ?
F1 C7 C6 N2 176.5(3) . . . . ?
F1 C7 C6 N3 -3.6(4) . . . . ?
O5 C10 C9 O4 72.5(4) . . . . ?
O5 C12 C11 S2 14.3(3) . . . . ?
O2 C2 C1 O1 -68.9(3) . . . . ?
N4 C16 C15 F2 -180.0(3) . . . . ?
N4 C16 C15 C14 -0.6(4) . . . . ?
N4 C12 C11 S2 -105.7(2) . . . . ?
N8 C24 C25 C26 0.1(6) . . . . ?
C5 N1 C8 C7 1.8(4) . . . . ?
C5 N1 C4 O2 120.8(3) . . . . ?
C5 N1 C4 C3 -119.2(3) . . . . ?
C5 N2 C6 C7 1.8(4) . . . . ?
C5 N2 C6 N3 -178.1(3) . . . . ?
C8 N1 C5 O3 176.7(3) . . . . ?
C8 N1 C5 N2 -3.9(4) . . . . ?
C8 N1 C4 O2 -55.1(3) . . . . ?
C8 N1 C4 C3 64.9(3) . . . . ?
C8 C7 C6 N2 -4.0(4) . . . . ?
C8 C7 C6 N3 175.9(3) . . . . ?
C16 N4 C13 O6 176.2(3) . . . . ?
C16 N4 C13 N5 -4.3(4) . . . . ?
C16 N4 C12 O5 -78.6(3) . . . . ?
C16 N4 C12 C11 42.9(4) . . . . ?
C16 C15 C14 N5 -1.3(4) . . . . ?
C16 C15 C14 N6 178.6(3) . . . . ?
C10 S2 C11 C12 -30.3(2) . . . . ?
C10 O5 C12 N4 140.3(2) . . . . ?
C10 O5 C12 C11 16.1(3) . . . . ?
C13 N5 C14 N6 -179.5(3) . . . . ?
C13 N5 C14 C15 0.3(4) . . . . ?
C13 N4 C16 C15 3.4(4) . . . . ?
C13 N4 C12 O5 93.5(3) . . . . ?
C13 N4 C12 C11 -145.0(3) . . . . ?
C6 N2 C5 O3 -178.7(3) . . . . ?
C6 N2 C5 N1 2.0(4) . . . . ?
C6 C7 C8 N1 2.1(4) . . . . ?
C12 O5 C10 S2 -39.1(3) . . . . ?
C12 O5 C10 C9 -163.6(3) . . . . ?
C12 N4 C16 C15 175.2(3) . . . . ?
C12 N4 C13 O6 4.1(4) . . . . ?
C12 N4 C13 N5 -176.4(2) . . . . ?
C2 S1 C3 C4 37.0(2) . . . . ?
C2 O2 C4 N1 147.9(3) . . . . ?
C2 O2 C4 C3 24.2(4) . . . . ?
C3 S1 C2 O2 -25.2(2) . . . . ?
C3 S1 C2 C1 96.7(2) . . . . ?
C19 C18 C17 N7 0.6(6) . . . . ?
C19 C20 C21 N7 1.6(5) . . . . ?
C19 C22 C23 C26 -179.6(3) . . . . ?
C4 O2 C2 S1 4.6(3) . . . . ?
C4 O2 C2 C1 -118.7(3) . . . . ?
C4 N1 C5 O3 0.8(4) . . . . ?
C4 N1 C5 N2 -179.9(2) . . . . ?
C4 N1 C8 C7 177.7(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C18 C19 C22 C23 -177.6(4) . . . . ?
C11 S2 C10 O5 40.1(2) . . . . ?
C11 S2 C10 C9 161.7(2) . . . . ?
C14 N5 C13 O6 -178.1(3) . . . . ?
C14 N5 C13 N4 2.4(4) . . . . ?
C26 C27 C28 N8 -2.5(6) . . . . ?
C24 N8 C28 C27 1.3(5) . . . . ?
C27 C26 C25 C24 -1.2(5) . . . . ?
C27 C26 C23 C22 156.7(4) . . . . ?
C20 C19 C18 C17 -1.7(5) . . . . ?
C20 C19 C22 C23 2.0(6) . . . . ?
C17 N7 C21 C20 -2.7(5) . . . . ?
C25 C26 C27 C28 2.4(5) . . . . ?
C25 C26 C23 C22 -25.0(6) . . . . ?
C22 C19 C18 C17 177.9(3) . . . . ?
C22 C19 C20 C21 -178.9(3) . . . . ?
C28 N8 C24 C25 -0.1(5) . . . . ?
C23 C26 C27 C28 -179.2(3) . . . . ?
C23 C26 C25 C24 -179.6(3) . . . . ?
C21 N7 C17 C18 1.7(5) . . . . ?

_olex2_submission_original_sample_id FTC-bpe
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_FTC-apy
_database_code_depnum_ccdc_archive 'CCDC 1981475'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
gonzalo-campillo-alvarado@uiowa.edu
elizabeth-keene@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            ?
_chemical_name_systematic        
"[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[4-azopyridine]'"
_chemical_formula_moiety         'C8 H9 F N3 O3 S, C8 H10 F N3 O3 S, C10 H8 N4'
_chemical_formula_sum            'C26 H27 F2 N10 O6 S2'
_chemical_formula_weight         677.69
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5024(8)
_cell_length_b                   11.2194(11)
_cell_length_c                   18.2134(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.538(5)
_cell_angle_gamma                90
_cell_volume                     1507.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.265
_cell_measurement_theta_min      2.2745
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0713 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.9738. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             702
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32670
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.893
_diffrn_reflns_theta_min         2.275
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D-8 Venture Duo-Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                6093
_reflns_number_total             7064
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 2297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7064
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.5135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1157
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N9-C19 \\sim N9B-C19
 with sigma of 0.02
 N9-N10 \\sim N9B-N10B
 with sigma of 0.02
 C24-N10 \\sim C24-N10B
 with sigma of 0.02
 N9-C24 \\sim N9B-C24
 with sigma of 0.04
 C19-N10 \\sim C19-N10B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(N10) = Uanis(N10B)
Uanis(N9B) = Uanis(N9)
4. Others
 Sof(N10B)=Sof(N9B)=1-FVAR(1)
 Sof(N9)=Sof(N10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C4(H4), C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C3(H3C,H3D), C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C22(H22), C9(H9), C17(H17), C23(H23), C26(H26), C18(H18),
 C21(H21), C20(H20), C25(H25)
5.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N6(H6A,H6B)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S2 S 0.21523(15) 0.65785(9) 1.16877(6) 0.0463(3) Uani 1 1 d . . . . .
S1 S -0.03878(16) 0.44652(11) 0.30789(5) 0.0503(3) Uani 1 1 d . . . . .
F1 F 0.2629(4) 0.1835(2) 0.63342(13) 0.0532(6) Uani 1 1 d . . . . .
F2 F 0.1763(4) 0.8172(2) 0.88634(14) 0.0592(7) Uani 1 1 d . . . . .
O5 O 0.3007(4) 0.4811(2) 1.09105(13) 0.0413(6) Uani 1 1 d . . . . .
O3 O -0.0080(5) 0.6173(3) 0.56988(16) 0.0565(9) Uani 1 1 d . . . . .
O6 O 0.0747(5) 0.3590(3) 0.93750(17) 0.0578(9) Uani 1 1 d . . . . .
O2 O 0.2178(4) 0.4773(3) 0.42543(14) 0.0473(7) Uani 1 1 d . . . . .
N1 N 0.0809(4) 0.4399(3) 0.52797(15) 0.0346(6) Uani 1 1 d . . . . .
N4 N 0.1100(4) 0.5476(3) 0.98301(15) 0.0325(6) Uani 1 1 d . . . . .
N5 N 0.0893(5) 0.5059(3) 0.85346(17) 0.0388(7) Uani 1 1 d . . . . .
O4 O 0.6175(5) 0.6341(4) 1.1568(2) 0.0735(12) Uani 1 1 d . . . . .
H4A H 0.625193 0.618401 1.113492 0.110 Uiso 1 1 calc GR . . . .
O1 O 0.4818(5) 0.3334(4) 0.3643(2) 0.0701(10) Uani 1 1 d . . . . .
H1 H 0.504927 0.350204 0.408880 0.105 Uiso 1 1 calc GR . . . .
N2 N 0.0804(5) 0.4746(3) 0.65662(16) 0.0404(7) Uani 1 1 d . . . . .
C8 C 0.1525(5) 0.3290(3) 0.5445(2) 0.0356(8) Uani 1 1 d . . . . .
H8 H 0.176807 0.279713 0.506464 0.043 Uiso 1 1 calc R . . . .
N8 N 0.6110(5) 0.5894(4) 0.9998(2) 0.0558(10) Uani 1 1 d . . . . .
N7 N 0.6085(6) 0.3857(4) 0.5203(2) 0.0615(11) Uani 1 1 d . . . . .
N3 N 0.1698(6) 0.3288(3) 0.74327(18) 0.0531(9) Uani 1 1 d . . . . .
H3A H 0.143121 0.374761 0.777452 0.064 Uiso 1 1 calc R . . . .
H3B H 0.212139 0.258580 0.754624 0.064 Uiso 1 1 calc R . . . .
C12 C 0.1152(5) 0.5019(3) 1.05853(19) 0.0338(8) Uani 1 1 d . . . . .
H12 H 0.050971 0.425407 1.054851 0.041 Uiso 1 1 calc R . . . .
C10 C 0.3438(6) 0.5218(4) 1.16604(19) 0.0401(9) Uani 1 1 d . . . . .
H10 H 0.302211 0.462636 1.198720 0.048 Uiso 1 1 calc R . . . .
C7 C 0.1876(5) 0.2915(3) 0.6150(2) 0.0367(8) Uani 1 1 d . . . . .
C4 C 0.0492(5) 0.4822(3) 0.45119(19) 0.0372(8) Uani 1 1 d . . . . .
H4 H 0.009159 0.565428 0.450458 0.045 Uiso 1 1 calc R . . . .
C5 C 0.0487(5) 0.5167(3) 0.58550(19) 0.0367(8) Uani 1 1 d . . . . .
C14 C 0.1432(5) 0.6652(4) 0.9706(2) 0.0362(7) Uani 1 1 d . . . . .
H14 H 0.164694 0.718982 1.010096 0.043 Uiso 1 1 calc R . . . .
C11 C 0.0292(5) 0.5846(4) 1.1094(2) 0.0392(8) Uani 1 1 d . . . . .
H11A H -0.041926 0.539067 1.138962 0.047 Uiso 1 1 calc R . . . .
H11B H -0.049235 0.642561 1.079932 0.047 Uiso 1 1 calc R . . . .
N6 N 0.1077(6) 0.6577(3) 0.77114(18) 0.0562(10) Uani 1 1 d . . . . .
H6A H 0.089535 0.607797 0.734678 0.067 Uiso 1 1 calc R . . . .
H6B H 0.122717 0.732055 0.762660 0.067 Uiso 1 1 calc R . . . .
C13 C 0.0897(5) 0.4640(3) 0.92420(19) 0.0362(8) Uani 1 1 d . . . . .
C3 C -0.0884(6) 0.4117(4) 0.3984(2) 0.0435(9) Uani 1 1 d . . . . .
H3C H -0.210682 0.435806 0.402034 0.052 Uiso 1 1 calc R . . . .
H3D H -0.075078 0.327022 0.408713 0.052 Uiso 1 1 calc R . . . .
C2 C 0.2023(6) 0.4466(4) 0.34840(19) 0.0432(9) Uani 1 1 d . . . . .
H2 H 0.262742 0.508078 0.323568 0.052 Uiso 1 1 calc R . . . .
C15 C 0.1442(6) 0.7013(3) 0.9013(2) 0.0371(8) Uani 1 1 d . . . . .
N9 N 0.6199(6) 0.4375(4) 0.7502(2) 0.0539(12) Uani 0.900(8) 1 d D . P A 1
C22 C 0.5788(7) 0.4814(5) 0.9702(3) 0.0594(12) Uani 1 1 d . . . . .
H22 H 0.555904 0.419825 1.001338 0.071 Uiso 1 1 calc R . . . .
C6 C 0.1459(5) 0.3660(3) 0.6733(2) 0.0356(8) Uani 1 1 d . . . . .
C1 C 0.2934(6) 0.3275(4) 0.3407(2) 0.0497(10) Uani 1 1 d . . . . .
H1A H 0.243912 0.268151 0.370128 0.060 Uiso 1 1 calc R . . . .
H1B H 0.266758 0.302429 0.288874 0.060 Uiso 1 1 calc R . . . .
C9 C 0.5435(7) 0.5367(6) 1.1886(3) 0.0655(14) Uani 1 1 d . . . . .
H9 H 0.614151 0.484739 1.221530 0.079 Uiso 1 1 calc R . . . .
C17 C 0.6620(7) 0.3036(5) 0.5714(3) 0.0609(12) Uani 1 1 d . . . . .
H17 H 0.696263 0.229692 0.555597 0.073 Uiso 1 1 calc R . . . .
C23 C 0.5773(7) 0.4549(5) 0.8956(3) 0.0591(11) Uani 1 1 d . . . . .
H23 H 0.554605 0.378089 0.877119 0.071 Uiso 1 1 calc R . . . .
C16 C 0.1124(5) 0.6197(4) 0.8408(2) 0.0377(8) Uani 1 1 d . . . . .
C26 C 0.6426(7) 0.6754(5) 0.9544(3) 0.0591(12) Uani 1 1 d . . . . .
H26 H 0.666435 0.751236 0.974388 0.071 Uiso 1 1 calc R . . . .
C18 C 0.6701(7) 0.3206(5) 0.6465(3) 0.0603(12) Uani 1 1 d . . . . .
H18 H 0.709563 0.260126 0.680484 0.072 Uiso 1 1 calc R . . . .
C19 C 0.6182(6) 0.4296(5) 0.6702(2) 0.0518(11) Uani 1 1 d D . . . .
C24 C 0.6112(6) 0.5482(5) 0.8497(2) 0.0521(11) Uani 1 1 d D . . . .
C21 C 0.5615(7) 0.4927(5) 0.5440(3) 0.0632(13) Uani 1 1 d . . . . .
H21 H 0.526554 0.552272 0.508830 0.076 Uiso 1 1 calc R . . . .
C20 C 0.5628(7) 0.5184(5) 0.6184(3) 0.0603(12) Uani 1 1 d . . . . .
H20 H 0.527568 0.592812 0.633060 0.072 Uiso 1 1 calc R . . . .
N10 N 0.6143(7) 0.5392(4) 0.7706(3) 0.0588(13) Uani 0.900(8) 1 d D . P A 1
C25 C 0.6426(7) 0.6603(5) 0.8800(3) 0.0624(12) Uani 1 1 d . . . . .
H25 H 0.663495 0.724440 0.850346 0.075 Uiso 1 1 calc R . . . .
N10B N 0.594(7) 0.465(3) 0.7857(15) 0.0588(13) Uani 0.100(8) 1 d D . P A 2
N9B N 0.618(6) 0.515(3) 0.7301(16) 0.0539(12) Uani 0.100(8) 1 d 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
S2 C10 1.811(4) . ?
S2 C11 1.801(4) . ?
S1 C3 1.799(4) . ?
S1 C2 1.824(4) . ?
F1 C7 1.354(4) . ?
F2 C15 1.359(4) . ?
O5 C12 1.429(5) . ?
O5 C10 1.420(4) . ?
O3 C5 1.221(5) . ?
O6 C13 1.212(5) . ?
O2 C4 1.428(5) . ?
O2 C2 1.428(4) . ?
N1 C8 1.367(5) . ?
N1 C4 1.455(4) . ?
N1 C5 1.412(4) . ?
N4 C12 1.462(4) . ?
N4 C14 1.369(5) . ?
N4 C13 1.411(4) . ?
N5 C13 1.371(5) . ?
N5 C16 1.314(5) . ?
O4 H4A 0.8200 . ?
O4 C9 1.399(7) . ?
O1 H1 0.8200 . ?
O1 C1 1.402(6) . ?
N2 C5 1.358(5) . ?
N2 C6 1.328(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.332(5) . ?
N8 C22 1.331(7) . ?
N8 C26 1.320(7) . ?
N7 C17 1.320(7) . ?
N7 C21 1.345(7) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C6 1.322(5) . ?
C12 H12 0.9800 . ?
C12 C11 1.535(5) . ?
C10 H10 0.9800 . ?
C10 C9 1.489(6) . ?
C7 C6 1.429(5) . ?
C4 H4 0.9800 . ?
C4 C3 1.501(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.327(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C16 1.333(5) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C2 H2 0.9800 . ?
C2 C1 1.520(6) . ?
C15 C16 1.418(5) . ?
N9 C19 1.458(6) . ?
N9 N10 1.203(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.370(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(7) . ?
C26 H26 0.9300 . ?
C26 C25 1.366(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(7) . ?
C19 C20 1.383(7) . ?
C19 N9B 1.45(2) . ?
C24 N10 1.448(6) . ?
C24 C25 1.376(7) . ?
C24 N10B 1.48(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.382(7) . ?
C20 H20 0.9300 . ?
C25 H25 0.9300 . ?
N10B N9B 1.20(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
C11 S2 C10 87.54(18) . . ?
C3 S1 C2 89.17(17) . . ?
C10 O5 C12 112.3(3) . . ?
C4 O2 C2 114.4(3) . . ?
C8 N1 C4 119.8(3) . . ?
C8 N1 C5 120.4(3) . . ?
C5 N1 C4 119.6(3) . . ?
C14 N4 C12 121.3(3) . . ?
C14 N4 C13 120.9(3) . . ?
C13 N4 C12 117.5(3) . . ?
C16 N5 C13 121.4(3) . . ?
C9 O4 H4A 109.5 . . ?
C1 O1 H1 109.5 . . ?
C6 N2 C5 122.0(3) . . ?
N1 C8 H8 120.0 . . ?
C7 C8 N1 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C26 N8 C22 116.8(4) . . ?
C17 N7 C21 117.4(4) . . ?
H3A N3 H3B 120.0 . . ?
C6 N3 H3A 120.0 . . ?
C6 N3 H3B 120.0 . . ?
O5 C12 N4 107.7(3) . . ?
O5 C12 H12 108.4 . . ?
O5 C12 C11 109.5(3) . . ?
N4 C12 H12 108.4 . . ?
N4 C12 C11 114.4(3) . . ?
C11 C12 H12 108.4 . . ?
S2 C10 H10 108.9 . . ?
O5 C10 S2 105.6(2) . . ?
O5 C10 H10 108.9 . . ?
O5 C10 C9 110.0(3) . . ?
C9 C10 S2 114.3(4) . . ?
C9 C10 H10 108.9 . . ?
F1 C7 C6 118.6(3) . . ?
C8 C7 F1 121.4(3) . . ?
C8 C7 C6 120.0(3) . . ?
O2 C4 N1 107.7(3) . . ?
O2 C4 H4 108.7 . . ?
O2 C4 C3 108.4(3) . . ?
N1 C4 H4 108.7 . . ?
N1 C4 C3 114.6(3) . . ?
C3 C4 H4 108.7 . . ?
O3 C5 N1 119.4(3) . . ?
O3 C5 N2 122.5(3) . . ?
N2 C5 N1 118.1(3) . . ?
N4 C14 H14 120.5 . . ?
C15 C14 N4 118.9(3) . . ?
C15 C14 H14 120.5 . . ?
S2 C11 H11A 110.6 . . ?
S2 C11 H11B 110.6 . . ?
C12 C11 S2 105.9(3) . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
H6A N6 H6B 120.0 . . ?
C16 N6 H6A 120.0 . . ?
C16 N6 H6B 120.0 . . ?
O6 C13 N4 119.7(3) . . ?
O6 C13 N5 122.5(3) . . ?
N5 C13 N4 117.8(3) . . ?
S1 C3 H3C 111.0 . . ?
S1 C3 H3D 111.0 . . ?
C4 C3 S1 103.8(3) . . ?
C4 C3 H3C 111.0 . . ?
C4 C3 H3D 111.0 . . ?
H3C C3 H3D 109.0 . . ?
S1 C2 H2 108.8 . . ?
O2 C2 S1 107.1(3) . . ?
O2 C2 H2 108.8 . . ?
O2 C2 C1 110.2(3) . . ?
C1 C2 S1 113.0(3) . . ?
C1 C2 H2 108.8 . . ?
F2 C15 C16 118.3(3) . . ?
C14 C15 F2 120.9(3) . . ?
C14 C15 C16 120.8(4) . . ?
N10 N9 C19 111.9(4) . . ?
N8 C22 H22 118.0 . . ?
N8 C22 C23 124.1(5) . . ?
C23 C22 H22 118.0 . . ?
N2 C6 C7 119.2(3) . . ?
N3 C6 N2 119.3(4) . . ?
N3 C6 C7 121.5(4) . . ?
O1 C1 C2 112.0(4) . . ?
O1 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O4 C9 C10 115.4(4) . . ?
O4 C9 H9 122.3 . . ?
C10 C9 H9 122.3 . . ?
N7 C17 H17 118.0 . . ?
N7 C17 C18 124.0(5) . . ?
C18 C17 H17 118.0 . . ?
C22 C23 H23 121.4 . . ?
C22 C23 C24 117.2(5) . . ?
C24 C23 H23 121.4 . . ?
N5 C16 N6 119.8(4) . . ?
N5 C16 C15 120.0(3) . . ?
N6 C16 C15 120.3(4) . . ?
N8 C26 H26 117.8 . . ?
N8 C26 C25 124.3(5) . . ?
C25 C26 H26 117.8 . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.2(5) . . ?
C19 C18 H18 120.9 . . ?
C18 C19 N9 114.6(4) . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 N9B 149.3(16) . . ?
C20 C19 N9 125.7(5) . . ?
C20 C19 N9B 89.9(15) . . ?
C23 C24 N10 125.7(5) . . ?
C23 C24 N10B 90.1(14) . . ?
C25 C24 C23 118.9(4) . . ?
C25 C24 N10 115.4(4) . . ?
C25 C24 N10B 151.0(14) . . ?
N7 C21 H21 118.5 . . ?
N7 C21 C20 123.1(5) . . ?
C20 C21 H21 118.5 . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.7(5) . . ?
C21 C20 H20 121.1 . . ?
N9 N10 C24 112.5(4) . . ?
C26 C25 C24 118.7(5) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
N9B N10B C24 112(3) . . ?
N10B N9B C19 111(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
S2 C10 C9 O4 -46.1(5) . . . . ?
S1 C2 C1 O1 173.1(3) . . . . ?
F1 C7 C6 N2 176.6(3) . . . . ?
F1 C7 C6 N3 -3.8(6) . . . . ?
F2 C15 C16 N5 176.8(4) . . . . ?
F2 C15 C16 N6 -2.5(6) . . . . ?
O5 C12 C11 S2 19.4(3) . . . . ?
O5 C10 C9 O4 72.5(5) . . . . ?
O2 C4 C3 S1 -39.3(4) . . . . ?
O2 C2 C1 O1 -67.0(5) . . . . ?
N1 C8 C7 F1 -178.2(3) . . . . ?
N1 C8 C7 C6 1.7(6) . . . . ?
N1 C4 C3 S1 -159.7(3) . . . . ?
N4 C12 C11 S2 -101.6(3) . . . . ?
N4 C14 C15 F2 179.9(4) . . . . ?
N4 C14 C15 C16 -0.3(6) . . . . ?
C8 N1 C4 O2 -57.0(4) . . . . ?
C8 N1 C4 C3 63.7(5) . . . . ?
C8 N1 C5 O3 176.9(4) . . . . ?
C8 N1 C5 N2 -3.9(5) . . . . ?
C8 C7 C6 N2 -3.3(6) . . . . ?
C8 C7 C6 N3 176.3(4) . . . . ?
N8 C22 C23 C24 -0.2(8) . . . . ?
N8 C26 C25 C24 -1.3(8) . . . . ?
N7 C17 C18 C19 0.5(8) . . . . ?
N7 C21 C20 C19 1.1(8) . . . . ?
C12 O5 C10 S2 -37.0(4) . . . . ?
C12 O5 C10 C9 -160.9(4) . . . . ?
C12 N4 C14 C15 177.3(3) . . . . ?
C12 N4 C13 O6 1.1(5) . . . . ?
C12 N4 C13 N5 -178.4(3) . . . . ?
C10 S2 C11 C12 -33.7(3) . . . . ?
C10 O5 C12 N4 136.4(3) . . . . ?
C10 O5 C12 C11 11.5(4) . . . . ?
C4 O2 C2 S1 8.3(4) . . . . ?
C4 O2 C2 C1 -115.0(4) . . . . ?
C4 N1 C8 C7 177.7(4) . . . . ?
C4 N1 C5 O3 1.0(6) . . . . ?
C4 N1 C5 N2 -179.7(3) . . . . ?
C5 N1 C8 C7 1.9(5) . . . . ?
C5 N1 C4 O2 118.8(4) . . . . ?
C5 N1 C4 C3 -120.4(4) . . . . ?
C5 N2 C6 N3 -178.3(4) . . . . ?
C5 N2 C6 C7 1.2(6) . . . . ?
C14 N4 C12 O5 -81.2(4) . . . . ?
C14 N4 C12 C11 40.8(5) . . . . ?
C14 N4 C13 O6 174.2(4) . . . . ?
C14 N4 C13 N5 -5.3(5) . . . . ?
C14 C15 C16 N5 -3.0(6) . . . . ?
C14 C15 C16 N6 177.7(4) . . . . ?
C11 S2 C10 O5 40.8(3) . . . . ?
C11 S2 C10 C9 161.9(3) . . . . ?
C13 N4 C12 O5 91.9(4) . . . . ?
C13 N4 C12 C11 -146.1(3) . . . . ?
C13 N4 C14 C15 4.4(6) . . . . ?
C13 N5 C16 N6 -178.7(4) . . . . ?
C13 N5 C16 C15 2.0(6) . . . . ?
C3 S1 C2 O2 -27.1(3) . . . . ?
C3 S1 C2 C1 94.4(3) . . . . ?
C2 S1 C3 C4 37.4(3) . . . . ?
C2 O2 C4 N1 144.9(3) . . . . ?
C2 O2 C4 C3 20.3(4) . . . . ?
N9 C19 C20 C21 -176.7(5) . . . . ?
C22 N8 C26 C25 0.6(8) . . . . ?
C22 C23 C24 N10 -179.5(5) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C22 C23 C24 N10B 179(2) . . . . ?
C6 N2 C5 O3 -178.5(4) . . . . ?
C6 N2 C5 N1 2.3(6) . . . . ?
C17 N7 C21 C20 -1.7(8) . . . . ?
C17 C18 C19 N9 176.3(5) . . . . ?
C17 C18 C19 C20 -1.0(7) . . . . ?
C17 C18 C19 N9B -163(3) . . . . ?
C23 C24 N10 N9 -13.9(8) . . . . ?
C23 C24 C25 C26 1.2(7) . . . . ?
C23 C24 N10B N9B -179(4) . . . . ?
C16 N5 C13 O6 -177.5(4) . . . . ?
C16 N5 C13 N4 2.0(5) . . . . ?
C26 N8 C22 C23 0.2(7) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C18 C19 N9B N10B -42(6) . . . . ?
C19 N9 N10 C24 178.5(4) . . . . ?
C24 N10B N9B C19 174(3) . . . . ?
C21 N7 C17 C18 0.8(8) . . . . ?
C20 C19 N9B N10B 154(4) . . . . ?
N10 N9 C19 C18 164.3(5) . . . . ?
N10 N9 C19 C20 -18.6(7) . . . . ?
N10 C24 C25 C26 -179.7(5) . . . . ?
C25 C24 N10 N9 167.0(5) . . . . ?
C25 C24 N10B N9B 0(7) . . . . ?
N10B C24 C25 C26 -178(4) . . . . ?
N9B C19 C20 C21 171.0(18) . . . . ?

_olex2_date_sample_data_collection 2019-09-17
_olex2_date_sample_submission    2019-09-03
_olex2_submission_original_sample_id FTC-apy
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_FTC-bipy
_database_code_depnum_ccdc_archive 'CCDC 1981476'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;University of Iowa
United States of America
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
loop_
_audit_author_email
gonzalo-campillo-alvarado@uiowa.edu
elizabeth-keene@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_systematic        
"[4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one]-[4,4'-bipyridine]"
_chemical_formula_moiety         '2(C8 H10 F N3 O3 S), 2(C10 H8 N2), H2 O'
_chemical_formula_sum            'C36 H38 F2 N10 O7 S2'
_chemical_formula_weight         824.895
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   7.4668(10)
_cell_length_b                   9.6700(14)
_cell_length_c                   26.187(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.087(4)
_cell_angle_gamma                90
_cell_volume                     1890.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.245
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0949 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.7869.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       irregular
_exptl_crystal_F_000             860.930
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.9933
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            48450
_diffrn_reflns_point_group_measured_fraction_full 0.9977
_diffrn_reflns_point_group_measured_fraction_max 0.9901
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.25
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9933
_diffrn_measurement_device_type  'Bruker D-8 Venture Duo-Photon 3'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          'Cystal is a pseudo-merohedral twin'
_reflns_Friedel_coverage         0.986
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              32
_reflns_limit_l_min              -32
_reflns_number_gt                7060
_reflns_number_total             7767
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.4154
_refine_diff_density_min         -0.3906
_refine_diff_density_rms         0.0777
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_d_res_high            0.7968
_refine_ls_d_res_low             9.0713
_refine_ls_goodness_of_fit_ref   1.0385
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    70
_refine_ls_number_parameters     508
_refine_ls_number_reflns         7767
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.0351
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+3.6194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          'Applied TWIN (100, 0-10, 00-1) and BASF 0.5'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5000(16)
 0.5000(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Rigid bond restraints
 H8, C29, C28, C27, N10, C31, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C29 \\sim C28 \\sim C27 \\sim N10 \\sim C31 \\sim C30: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
5.a Free rotating group:
 O7(H7a,H7b)
5.b Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C4(H4), C2(H2)
5.c Secondary CH2 refined with riding coordinates:
 C3(H3c,H3d), C11(H11a,H11b), C9(H9a,H9b), C1(H1a,H1b)
5.d Aromatic/amide H refined with riding coordinates:
 C24(H24), C16(H16), C21(H21), C28(H28), C27(H27), C31(H31), C30(H30),
 C20(H20), C35(H35), C18(H18), C33(H33), C32(H32), C23(H23), C25(H25), C8(H8),
 C26(H26), C36(H36), C17(H17)
5.e Fitted hexagon refined as free rotating group:
 C29(C28,C27,N10,C31,C30)
5.f X=CH2 refined with riding coordinates:
 N3(H3a,H3b), N6(H6a,H6b)
5.g Idealised tetrahedral OH refined as rotating group:
 O4(H4a), O1(H1)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.1447(2) 0.48180(15) 0.03187(6) 0.0388(3) Uani 1.000000 . .
S2 S 0.6198(2) 0.57708(17) 0.50297(6) 0.0431(4) Uani 1.000000 . .
F2 F 1.3659(5) 0.6700(4) 0.63169(13) 0.0456(9) Uani 1.000000 . .
F1 F 0.8862(5) 0.3374(4) -0.09412(13) 0.0406(8) Uani 1.000000 . .
O6 O 0.7112(5) 0.5588(5) 0.69950(14) 0.0359(9) Uani 1.000000 . .
O3 O 0.2342(5) 0.4770(4) -0.16226(15) 0.0345(9) Uani 1.000000 . .
O2 O 0.2576(5) 0.2950(4) -0.03348(15) 0.0329(9) Uani 1.000000 . .
O5 O 0.7310(6) 0.7465(4) 0.57531(14) 0.0355(9) Uani 1.000000 . .
C15 C 1.1996(7) 0.6320(5) 0.6469(2) 0.0299(12) Uani 1.000000 . .
C6 C 0.6942(9) 0.4272(6) -0.1596(2) 0.0339(13) Uani 1.000000 . .
N1 N 0.4171(6) 0.4144(5) -0.09492(18) 0.0299(11) Uani 1.000000 . .
C12 C 0.7408(8) 0.6121(6) 0.59552(19) 0.0328(14) Uani 1.000000 . .
H12 H 0.6267(8) 0.5901(6) 0.61377(19) 0.0393(16) Uiso 1.000000 R .
N2 N 0.5309(6) 0.4573(4) -0.17794(18) 0.0271(10) Uani 1.000000 . .
C5 C 0.3863(8) 0.4497(6) -0.1463(2) 0.0323(12) Uani 1.000000 . .
C24 C 0.3769(10) 0.5961(8) 0.3945(2) 0.0484(16) Uani 1.000000 . .
H24 H 0.3421(10) 0.5530(8) 0.4255(2) 0.058(2) Uiso 1.000000 R .
C22 C 0.4044(8) 0.5858(6) 0.3040(2) 0.0346(12) Uani 1.000000 . .
C16 C 1.0607(8) 0.6439(7) 0.6145(2) 0.0366(14) Uani 1.000000 . .
H16 H 1.0784(8) 0.6746(7) 0.5804(2) 0.0439(16) Uiso 1.000000 R .
N3 N 0.8339(7) 0.4436(5) -0.19092(18) 0.0423(13) Uani 1.000000 . .
H3a H 0.8169(7) 0.4732(5) -0.22234(18) 0.0508(15) Uiso 1.000000 R .
H3b H 0.9429(7) 0.4249(5) -0.18013(18) 0.0508(15) Uiso 1.000000 R .
O4 O 0.9719(6) 0.7525(5) 0.49021(18) 0.0467(12) Uani 1.000000 . .
H4a H 0.966(4) 0.691(6) 0.468(2) 0.0700(17) Uiso 1.000000 GR .
N4 N 0.8902(6) 0.6103(5) 0.63202(17) 0.0342(12) Uani 1.000000 . .
N5 N 1.0108(6) 0.5605(5) 0.71447(17) 0.0287(10) Uani 1.000000 . .
C21 C 0.3324(11) 0.5114(7) 0.1635(2) 0.0517(18) Uani 1.000000 . .
H21 H 0.3099(11) 0.5631(7) 0.1333(2) 0.062(2) Uiso 1.000000 R .
C29 C 0.8792(6) 0.5322(3) 0.23102(10) 0.0378(14) Uani 1.000000 . U
C28 C 0.8872(6) 0.3927(3) 0.21847(12) 0.0471(16) Uani 1.000000 G U
H28 H 0.9086(6) 0.3258(3) 0.24433(12) 0.0565(19) Uiso 1.000000 R .
C27 C 0.8638(7) 0.3511(3) 0.16810(14) 0.0450(15) Uani 1.000000 G U
H27 H 0.8692(7) 0.2557(3) 0.15952(14) 0.0540(18) Uiso 1.000000 R .
N10 N 0.8324(6) 0.4490(4) 0.13027(11) 0.0502(14) Uani 1.000000 G U
C31 C 0.8244(6) 0.5885(3) 0.14282(12) 0.0484(15) Uani 1.000000 G U
H31 H 0.8030(6) 0.6555(3) 0.11696(12) 0.0581(18) Uiso 1.000000 R .
C30 C 0.8478(6) 0.6302(3) 0.19319(13) 0.0432(14) Uani 1.000000 G U
H30 H 0.8424(6) 0.7255(3) 0.20177(13) 0.0518(17) Uiso 1.000000 R .
C20 C 0.3530(9) 0.5788(6) 0.2087(2) 0.0400(13) Uani 1.000000 . .
H20 H 0.3463(9) 0.6769(6) 0.2087(2) 0.0480(16) Uiso 1.000000 R .
C13 C 0.8670(6) 0.5748(5) 0.68312(19) 0.0255(10) Uani 1.000000 . .
N9 N 0.9374(9) 0.6537(7) 0.3887(2) 0.0520(15) Uani 1.000000 . .
C35 C 0.9694(8) 0.7034(6) 0.2991(2) 0.0371(14) Uani 1.000000 . .
H35 H 1.0005(8) 0.7681(6) 0.2733(2) 0.0445(16) Uiso 1.000000 R .
C18 C 0.3910(9) 0.3709(6) 0.2514(2) 0.0414(14) Uani 1.000000 . .
H18 H 0.4093(9) 0.3180(6) 0.2815(2) 0.0496(17) Uiso 1.000000 R .
N7 N 0.3435(8) 0.3738(6) 0.16082(19) 0.0427(12) Uani 1.000000 . .
O1 O 0.3581(6) 0.2174(4) 0.07166(15) 0.0414(10) Uani 1.000000 . .
H1 H 0.3416(7) 0.251(7) 0.1008(11) 0.0621(15) Uiso 1.000000 GR .
O7 O 0.6678(7) 0.3631(5) 0.03724(18) 0.0517(12) Uani 1.000000 . .
H7a H 0.687(11) 0.409(7) 0.0653(15) 0.0775(18) Uiso 1.000000 G .
H7b H 0.589(9) 0.301(6) 0.046(2) 0.0775(18) Uiso 1.000000 G .
N8 N 0.4467(9) 0.7244(6) 0.3980(2) 0.0482(14) Uani 1.000000 . .
C14 C 1.1734(7) 0.5874(6) 0.6981(2) 0.0288(11) Uani 1.000000 . .
C10 C 0.6691(9) 0.7531(6) 0.5236(2) 0.0387(14) Uani 1.000000 . .
H10 H 0.5547(9) 0.8068(6) 0.5231(2) 0.0464(16) Uiso 1.000000 R .
C33 C 0.8418(8) 0.4926(7) 0.3254(2) 0.0403(14) Uani 1.000000 . .
H33 H 0.7818(8) 0.4081(7) 0.3183(2) 0.0483(16) Uiso 1.000000 R .
C4 C 0.2678(7) 0.4256(5) -0.0578(2) 0.0277(12) Uani 1.000000 . .
H4 H 0.1529(7) 0.4474(5) -0.0757(2) 0.0332(14) Uiso 1.000000 R .
N6 N 1.3170(6) 0.5660(5) 0.72858(17) 0.0329(10) Uani 1.000000 . .
H6a H 1.4257(6) 0.5797(5) 0.71671(17) 0.0395(12) Uiso 1.000000 R .
H6b H 1.3017(6) 0.5385(5) 0.76030(17) 0.0395(12) Uiso 1.000000 R .
C7 C 0.7196(7) 0.3787(5) -0.1098(2) 0.0262(11) Uani 1.000000 . .
C32 C 0.8649(10) 0.5319(7) 0.3757(2) 0.0470(16) Uani 1.000000 . .
H32 H 0.8282(10) 0.4705(7) 0.4020(2) 0.0564(19) Uiso 1.000000 R .
C3 C 0.3047(8) 0.5304(5) -0.0163(2) 0.0368(14) Uani 1.000000 . .
H3c H 0.2836(8) 0.6259(5) -0.0285(2) 0.0442(16) Uiso 1.000000 R .
H3d H 0.4290(8) 0.5227(5) -0.0034(2) 0.0442(16) Uiso 1.000000 R .
C23 C 0.3509(7) 0.5204(6) 0.3497(2) 0.0363(13) Uani 1.000000 . .
H23 H 0.3003(7) 0.4303(6) 0.3500(2) 0.0436(15) Uiso 1.000000 R .
C25 C 0.4909(10) 0.7814(7) 0.3537(2) 0.0478(17) Uani 1.000000 . .
H25 H 0.5393(10) 0.8722(7) 0.3544(2) 0.057(2) Uiso 1.000000 R .
C8 C 0.5821(8) 0.3756(7) -0.0774(2) 0.0353(13) Uani 1.000000 . .
H8 H 0.5984(8) 0.3472(7) -0.0429(2) 0.0423(16) Uiso 1.000000 R U
C2 C 0.1380(9) 0.3000(6) 0.0080(2) 0.0355(13) Uani 1.000000 . .
H2 H 0.0143(9) 0.2785(6) -0.0044(2) 0.0426(15) Uiso 1.000000 R .
C11 C 0.7663(8) 0.5123(6) 0.5523(2) 0.0347(13) Uani 1.000000 . .
H11a H 0.7317(8) 0.4174(6) 0.5626(2) 0.0416(16) Uiso 1.000000 R .
H11b H 0.8924(8) 0.5116(6) 0.5407(2) 0.0416(16) Uiso 1.000000 R .
C19 C 0.3830(8) 0.5124(6) 0.2544(2) 0.0357(13) Uani 1.000000 . .
C26 C 0.4715(9) 0.7179(6) 0.3068(3) 0.0401(14) Uani 1.000000 . .
H26 H 0.5044(9) 0.7655(6) 0.2765(3) 0.0481(17) Uiso 1.000000 R .
C36 C 0.9891(9) 0.7373(7) 0.3512(3) 0.0457(16) Uani 1.000000 . .
H36 H 1.0416(9) 0.8237(7) 0.3598(3) 0.0548(19) Uiso 1.000000 R .
C17 C 0.3726(10) 0.3038(7) 0.2047(2) 0.0471(16) Uani 1.000000 . .
H17 H 0.3808(10) 0.2058(7) 0.2036(2) 0.0566(19) Uiso 1.000000 R .
C34 C 0.9019(8) 0.5705(7) 0.2860(2) 0.0367(13) Uani 1.000000 . .
C9 C 0.8045(9) 0.8304(6) 0.4915(2) 0.0413(15) Uani 1.000000 . .
H9a H 0.8259(9) 0.9232(6) 0.5062(2) 0.0496(18) Uiso 1.000000 R .
H9b H 0.7579(9) 0.8422(6) 0.4563(2) 0.0496(18) Uiso 1.000000 R .
C1 C 0.1916(9) 0.1957(6) 0.0476(2) 0.0422(15) Uani 1.000000 . .
H1a H 0.1936(9) 0.1033(6) 0.0314(2) 0.0506(18) Uiso 1.000000 R .
H1b H 0.0978(9) 0.1938(6) 0.0743(2) 0.0506(18) Uiso 1.000000 R .


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 C3 1.801(6) . ?
S1 C2 1.866(6) . ?
S2 C10 1.823(7) . ?
S2 C11 1.804(6) . ?
F2 C15 1.355(6) . ?
F1 C7 1.368(6) . ?
O6 C13 1.250(6) . ?
O3 C5 1.238(7) . ?
O2 C4 1.417(6) . ?
O2 C2 1.407(7) . ?
O5 C12 1.406(7) . ?
O5 C10 1.432(7) . ?
C15 C16 1.344(8) . ?
C15 C14 1.422(8) . ?
C6 N2 1.342(8) . ?
C6 N3 1.338(8) . ?
C6 C7 1.399(8) . ?
N1 C5 1.407(7) . ?
N1 C4 1.485(6) . ?
N1 C8 1.367(7) . ?
C12 N4 1.468(7) . ?
C12 C11 1.500(7) . ?
N2 C5 1.363(7) . ?
C24 N8 1.349(9) . ?
C24 C23 1.395(9) . ?
C22 C23 1.412(8) . ?
C22 C19 1.487(8) . ?
C22 C26 1.374(8) . ?
C16 N4 1.392(7) . ?
O4 C9 1.459(8) . ?
N4 C13 1.392(7) . ?
N5 C13 1.358(6) . ?
N5 C14 1.314(7) . ?
C21 C20 1.359(8) . ?
C21 N7 1.335(9) . ?
C29 C28 1.3900 . ?
C29 C30 1.3900 . ?
C29 C34 1.495(6) . ?
C28 C27 1.3900 . ?
C27 N10 1.3900 . ?
N10 C31 1.3900 . ?
C31 C30 1.3900 . ?
C20 C19 1.377(8) . ?
N9 C32 1.339(9) . ?
N9 C36 1.331(8) . ?
C35 C36 1.409(9) . ?
C35 C34 1.422(9) . ?
C18 C19 1.372(8) . ?
C18 C17 1.391(8) . ?
N7 C17 1.351(8) . ?
O1 C1 1.408(7) . ?
N8 C25 1.325(8) . ?
C14 N6 1.352(6) . ?
C10 C9 1.513(8) . ?
C33 C32 1.381(9) . ?
C33 C34 1.356(8) . ?
C4 C3 1.510(8) . ?
C7 C8 1.333(7) . ?
C25 C26 1.382(9) . ?
C2 C1 1.502(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
C2 S1 C3 91.6(2) . . ?
C11 S2 C10 89.5(3) . . ?
C2 O2 C4 110.5(4) . . ?
C10 O5 C12 114.5(4) . . ?
C16 C15 F2 119.8(5) . . ?
C14 C15 F2 119.1(5) . . ?
C14 C15 C16 120.9(5) . . ?
N3 C6 N2 117.6(5) . . ?
C7 C6 N2 122.0(5) . . ?
C7 C6 N3 120.5(6) . . ?
C4 N1 C5 119.2(4) . . ?
C8 N1 C5 122.3(5) . . ?
C8 N1 C4 118.5(5) . . ?
N4 C12 O5 107.2(5) . . ?
C11 C12 O5 108.5(4) . . ?
C11 C12 N4 112.7(5) . . ?
C5 N2 C6 119.3(5) . . ?
N1 C5 O3 121.5(5) . . ?
N2 C5 O3 120.7(5) . . ?
N2 C5 N1 117.8(5) . . ?
C23 C24 N8 126.4(6) . . ?
C19 C22 C23 119.8(5) . . ?
C26 C22 C23 118.3(6) . . ?
C26 C22 C19 121.9(6) . . ?
N4 C16 C15 118.5(5) . . ?
C16 N4 C12 118.5(4) . . ?
C13 N4 C12 122.2(4) . . ?
C13 N4 C16 119.3(4) . . ?
C14 N5 C13 120.8(5) . . ?
N7 C21 C20 121.1(6) . . ?
C30 C29 C28 120.0 . . ?
C34 C29 C28 117.6 . . ?
C34 C29 C30 122.4 . . ?
C27 C28 C29 120.0 . . ?
N10 C27 C28 120.0 . . ?
C31 N10 C27 120.0 . . ?
C30 C31 N10 120.0 . . ?
C31 C30 C29 120.0 . . ?
C19 C20 C21 123.5(6) . . ?
N4 C13 O6 118.5(4) . . ?
N5 C13 O6 121.0(5) . . ?
N5 C13 N4 120.5(4) . . ?
C36 N9 C32 117.6(6) . . ?
C34 C35 C36 118.7(6) . . ?
C17 C18 C19 120.9(6) . . ?
C17 N7 C21 117.7(6) . . ?
C25 N8 C24 114.8(6) . . ?
N5 C14 C15 119.8(5) . . ?
N6 C14 C15 119.5(5) . . ?
N6 C14 N5 120.6(5) . . ?
O5 C10 S2 107.6(4) . . ?
C9 C10 S2 115.6(4) . . ?
C9 C10 O5 109.4(5) . . ?
C34 C33 C32 122.1(7) . . ?
N1 C4 O2 105.7(4) . . ?
C3 C4 O2 106.6(4) . . ?
C3 C4 N1 112.6(5) . . ?
C6 C7 F1 119.9(5) . . ?
C8 C7 F1 120.2(5) . . ?
C8 C7 C6 119.8(5) . . ?
C33 C32 N9 122.3(6) . . ?
C4 C3 S1 102.0(4) . . ?
C22 C23 C24 116.0(6) . . ?
C26 C25 N8 124.6(7) . . ?
C7 C8 N1 118.3(5) . . ?
O2 C2 S1 105.9(4) . . ?
C1 C2 S1 113.2(4) . . ?
C1 C2 O2 110.0(5) . . ?
C12 C11 S2 103.8(4) . . ?
C20 C19 C22 123.6(5) . . ?
C18 C19 C22 121.5(5) . . ?
C18 C19 C20 114.9(6) . . ?
C25 C26 C22 119.9(6) . . ?
C35 C36 N9 122.9(7) . . ?
N7 C17 C18 121.9(6) . . ?
C35 C34 C29 119.7(5) . . ?
C33 C34 C29 124.0(6) . . ?
C33 C34 C35 115.8(6) . . ?
C10 C9 O4 109.3(5) . . ?
C2 C1 O1 116.3(5) . . ?

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
S1 C3 C4 O2 -46.7(4) . . . . ?
S1 C3 C4 N1 -162.1(3) . . . . ?
S1 C2 O2 C4 -29.1(5) . . . . ?
S1 C2 C1 O1 -53.7(4) . . . . ?
S2 C10 O5 C12 1.3(5) . . . . ?
S2 C10 C9 O4 -57.4(4) . . . . ?
S2 C11 C12 O5 -40.7(4) . . . . ?
S2 C11 C12 N4 -159.2(3) . . . . ?
F2 C15 C16 N4 -177.0(5) . . . . ?
F2 C15 C14 N5 174.8(5) . . . . ?
F2 C15 C14 N6 -8.8(6) . . . . ?
F1 C7 C6 N2 174.1(5) . . . . ?
F1 C7 C6 N3 -5.1(6) . . . . ?
F1 C7 C8 N1 -178.4(5) . . . . ?
O6 C13 N4 C12 -7.9(7) . . . . ?
O6 C13 N4 C16 172.8(6) . . . . ?
O6 C13 N5 C14 -174.9(5) . . . . ?
O3 C5 N1 C4 -7.1(7) . . . . ?
O3 C5 N1 C8 175.8(5) . . . . ?
O3 C5 N2 C6 180.0(5) . . . . ?
O2 C4 N1 C5 127.0(4) . . . . ?
O2 C4 N1 C8 -55.8(5) . . . . ?
O2 C2 C1 O1 64.5(5) . . . . ?
O5 C12 N4 C16 -58.9(5) . . . . ?
O5 C12 N4 C13 121.8(4) . . . . ?
O5 C10 C9 O4 64.3(5) . . . . ?
C15 C16 N4 C12 -174.9(6) . . . . ?
C15 C16 N4 C13 4.4(7) . . . . ?
C15 C14 N5 C13 -0.1(7) . . . . ?
C6 N2 C5 N1 2.0(6) . . . . ?
C6 C7 C8 N1 3.1(6) . . . . ?
C12 N4 C13 N5 173.2(5) . . . . ?
C24 N8 C25 C26 -0.7(8) . . . . ?
C24 C23 C22 C19 179.5(5) . . . . ?
C24 C23 C22 C26 -2.0(7) . . . . ?
C22 C19 C20 C21 -179.6(7) . . . . ?
C22 C19 C18 C17 -179.3(7) . . . . ?
C22 C26 C25 N8 -0.9(8) . . . . ?
C16 N4 C13 N5 -6.1(6) . . . . ?
N4 C13 N5 C14 3.9(7) . . . . ?
C21 C20 C19 C18 -0.0(8) . . . . ?
C21 N7 C17 C18 -0.1(8) . . . . ?
C29 C28 C27 N10 0.0(3) . . . . ?
C29 C30 C31 N10 -0.0(4) . . . . ?
C29 C34 C35 C36 179.8(5) . . . . ?
C29 C34 C33 C32 -179.8(6) . . . . ?
C28 C27 N10 C31 -0.0(4) . . . . ?
C27 N10 C31 C30 0.0(3) . . . . ?
C20 C19 C18 C17 1.1(7) . . . . ?
N9 C32 C33 C34 4.6(8) . . . . ?
N9 C36 C35 C34 -4.1(8) . . . . ?
C35 C34 C33 C32 -7.8(7) . . . . ?


_olex2_date_sample_data_collection 2020-01-08
_olex2_date_sample_submission    2020-01-07
_olex2_submission_original_sample_id FTC-bipy
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
C29 C28 0.0100 0.0409 -0.0288
C29 C27 0.0100 0.0491 0.0020
C29 C31 0.0100 0.0510 0.0107
C29 C30 0.0100 0.0298 0.0061
C28 C27 0.0100 0.0513 -0.0047
C28 N10 0.0100 0.0403 -0.0042
C28 C30 0.0100 0.0392 0.0107
C27 N10 0.0100 0.0414 -0.0038
C27 C31 0.0100 0.0422 -0.0166
N10 C31 0.0100 0.0567 -0.0100
N10 C30 0.0100 0.0555 -0.0095
C31 C30 0.0100 0.0550 0.0038

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C29 C28 0.0400
C29 C30 0.0400
C28 C27 0.0400
C27 N10 0.0400
N10 C31 0.0400
C31 C30 0.0400

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5000(16)
2 0.5000(16)

