# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2130547'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 F N3 O3, C8 H12 N O, C H4 O'
_chemical_formula_sum            'C25 H33 F N4 O5'
_chemical_formula_weight         488.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4159(11)
_cell_length_b                   12.6978(17)
_cell_length_c                   13.8293(17)
_cell_angle_alpha                105.309(4)
_cell_angle_beta                 107.316(4)
_cell_angle_gamma                101.130(4)
_cell_volume                     1300.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2941
_cell_measurement_theta_min      2.555
_cell_measurement_theta_max      30.368

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.7022
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9474
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5013
_reflns_number_gt                3182
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5013
_refine_ls_number_parameters     433
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0734(2) 1.22799(13) 0.50074(13) 0.0596(5) Uani 1 1 d . . . . .
O1 O 0.3770(3) 1.08004(15) 0.77384(14) 0.0515(5) Uani 1 1 d . . . . .
O2 O 0.4843(3) 0.76268(16) 0.74749(16) 0.0593(6) Uani 1 1 d . . . . .
O3 O 0.5314(3) 0.93278(16) 0.86307(15) 0.0531(5) Uani 1 1 d . . . . .
N1 N 0.3296(3) 0.85933(17) 0.48395(16) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.0602(3) 1.09738(18) 0.30184(17) 0.0452(6) Uani 1 1 d . . . . .
N3 N -0.0703(3) 1.1497(2) 0.10703(18) 0.0495(6) Uani 1 1 d . . . . .
C1 C 0.3596(3) 1.0084(2) 0.6876(2) 0.0369(6) Uani 1 1 d . . . . .
C2 C 0.4093(3) 0.9042(2) 0.6766(2) 0.0380(6) Uani 1 1 d . . . . .
C3 C 0.3909(3) 0.8370(2) 0.5760(2) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.4796(3) 0.8644(2) 0.7692(2) 0.0401(6) Uani 1 1 d . . . . .
C5 C 0.3148(4) 0.7763(3) 0.3818(2) 0.0484(7) Uani 1 1 d . . . . .
C6 C 0.1354(6) 0.6942(4) 0.3202(3) 0.0772(11) Uani 1 1 d . . . . .
C8 C 0.2840(3) 1.0275(2) 0.58628(19) 0.0366(6) Uani 1 1 d . . . . .
C9 C 0.2192(4) 1.1221(2) 0.5880(2) 0.0406(6) Uani 1 1 d . . . . .
C10 C 0.1474(4) 1.1410(2) 0.4953(2) 0.0418(6) Uani 1 1 d . . . . .
C11 C 0.1394(3) 1.0736(2) 0.3940(2) 0.0393(6) Uani 1 1 d . . . . .
C12 C 0.2023(4) 0.9806(2) 0.3920(2) 0.0408(6) Uani 1 1 d . . . . .
C13 C 0.2710(3) 0.9552(2) 0.4863(2) 0.0369(6) Uani 1 1 d . . . . .
C14 C 0.1216(4) 1.2139(2) 0.3007(2) 0.0486(7) Uani 1 1 d . . . . .
C15 C -0.0174(5) 1.2343(3) 0.2144(2) 0.0512(8) Uani 1 1 d . . . . .
C16 C 0.0177(4) 1.0106(3) 0.1957(2) 0.0484(7) Uani 1 1 d . . . . .
C17 C -0.1183(4) 1.0339(3) 0.1111(2) 0.0471(7) Uani 1 1 d . . . . .
H3 H 0.418(3) 0.771(2) 0.569(2) 0.041(7) Uiso 1 1 d . . . . .
H9 H 0.223(3) 1.174(2) 0.656(2) 0.041(7) Uiso 1 1 d . . . . .
H12 H 0.195(3) 0.9371(18) 0.3267(19) 0.021(6) Uiso 1 1 d . . . . .
H31 H 0.026(4) 1.161(2) 0.085(2) 0.058(9) Uiso 1 1 d . . . . .
H51 H 0.393(4) 0.732(2) 0.399(2) 0.059(9) Uiso 1 1 d . . . . .
H52 H 0.343(4) 0.815(2) 0.335(2) 0.052(8) Uiso 1 1 d . . . . .
H61 H 0.135(5) 0.635(3) 0.256(3) 0.092(12) Uiso 1 1 d . . . . .
H62 H 0.100(5) 0.646(3) 0.361(3) 0.091(13) Uiso 1 1 d . . . . .
H63 H 0.041(5) 0.734(3) 0.309(3) 0.095(13) Uiso 1 1 d . . . . .
H141 H 0.228(4) 1.216(2) 0.284(2) 0.061(9) Uiso 1 1 d . . . . .
H142 H 0.148(3) 1.269(2) 0.379(2) 0.050(7) Uiso 1 1 d . . . . .
H151 H 0.028(4) 1.308(3) 0.215(3) 0.079(11) Uiso 1 1 d . . . . .
H152 H -0.131(4) 1.233(2) 0.236(2) 0.054(8) Uiso 1 1 d . . . . .
H161 H -0.044(4) 0.932(3) 0.194(2) 0.060(9) Uiso 1 1 d . . . . .
H162 H 0.125(4) 1.005(2) 0.174(2) 0.045(7) Uiso 1 1 d . . . . .
H171 H -0.227(4) 1.028(2) 0.128(2) 0.059(9) Uiso 1 1 d . . . . .
H172 H -0.136(4) 0.979(2) 0.044(2) 0.051(8) Uiso 1 1 d . . . . .
O21 O 0.7175(3) 0.75242(15) 0.91680(18) 0.0526(5) Uani 1 1 d . . . . .
N21 N 0.5880(4) 0.15697(18) 0.9944(2) 0.0409(6) Uani 1 1 d . . . . .
C21 C 0.7119(4) 0.6450(2) 0.9177(2) 0.0436(7) Uani 1 1 d . . . . .
C22 C 0.8139(4) 0.6319(3) 1.0100(3) 0.0557(8) Uani 1 1 d . . . . .
C23 C 0.8116(4) 0.5250(3) 1.0151(3) 0.0552(8) Uani 1 1 d . . . . .
C24 C 0.7095(4) 0.4273(2) 0.9286(2) 0.0447(7) Uani 1 1 d . . . . .
C25 C 0.6069(5) 0.4415(3) 0.8380(3) 0.0575(8) Uani 1 1 d . . . . .
C26 C 0.6071(5) 0.5481(3) 0.8312(3) 0.0570(8) Uani 1 1 d . . . . .
C27 C 0.7077(5) 0.3098(3) 0.9348(3) 0.0531(8) Uani 1 1 d . . . . .
C28 C 0.5899(4) 0.2730(2) 0.9916(2) 0.0426(7) Uani 1 1 d . . . . .
H21 H 0.620(6) 0.743(3) 0.844(3) 0.111(14) Uiso 1 1 d . . . . .
H22 H 0.873(4) 0.700(3) 1.073(3) 0.078(10) Uiso 1 1 d . . . . .
H23 H 0.888(4) 0.520(3) 1.078(3) 0.065(9) Uiso 1 1 d . . . . .
H25 H 0.534(4) 0.383(3) 0.782(3) 0.073(11) Uiso 1 1 d . . . . .
H26 H 0.538(5) 0.554(3) 0.773(3) 0.094(13) Uiso 1 1 d . . . . .
H27 H 0.705(4) 0.150(2) 1.025(2) 0.053(8) Uiso 1 1 d . . . . .
H28 H 0.529(4) 0.136(3) 1.038(3) 0.065(9) Uiso 1 1 d . . . . .
H29 H 0.543(4) 0.103(3) 0.921(3) 0.077(10) Uiso 1 1 d . . . . .
H271 H 0.667(4) 0.247(3) 0.867(3) 0.066(10) Uiso 1 1 d . . . . .
H272 H 0.819(4) 0.310(2) 0.972(2) 0.051(8) Uiso 1 1 d . . . . .
H281 H 0.461(4) 0.272(2) 0.952(2) 0.053(8) Uiso 1 1 d . . . . .
H282 H 0.624(3) 0.325(2) 1.066(2) 0.044(7) Uiso 1 1 d . . . . .
O18 O 0.2901(10) 0.5636(6) 0.5811(6) 0.145(3) Uiso 0.579(6) 1 d D . P A -1
H18 H 0.350283 0.625601 0.632953 0.217 Uiso 0.579(6) 1 d R U P A -1
C18 C 0.1323(17) 0.5297(14) 0.5905(13) 0.246(8) Uiso 0.579(6) 1 d D . P A -1
H18A H 0.146178 0.498936 0.647872 0.370 Uiso 0.579(6) 1 calc R U P A -1
H18B H 0.051486 0.472216 0.524084 0.370 Uiso 0.579(6) 1 calc R U P A -1
H18C H 0.088749 0.594190 0.606151 0.370 Uiso 0.579(6) 1 calc R U P A -1
O19 O 0.4955(18) 0.5691(10) 0.4651(10) 0.189(5) Uiso 0.421(6) 1 d D . P A -2
H19 H 0.560251 0.528392 0.450722 0.284 Uiso 0.421(6) 1 d R U P A -2
C19 C 0.409(3) 0.5309(19) 0.5245(16) 0.211(9) Uiso 0.421(6) 1 d D . P A -2
H19A H 0.405635 0.452730 0.515461 0.317 Uiso 0.421(6) 1 calc R U P A -2
H19B H 0.292511 0.536121 0.500581 0.317 Uiso 0.421(6) 1 calc R U P A -2
H19C H 0.468806 0.576918 0.599303 0.317 Uiso 0.421(6) 1 calc R U P A -2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.364(3) . ?
O1 C1 1.242(3) . ?
O2 C4 1.258(3) . ?
O3 C4 1.245(3) . ?
N1 C3 1.350(3) . ?
N1 C13 1.396(3) . ?
N1 C5 1.477(3) . ?
N2 C11 1.391(3) . ?
N2 C16 1.475(3) . ?
N2 C14 1.476(3) . ?
N3 C15 1.462(4) . ?
N3 C17 1.469(4) . ?
N3 H31 0.95(3) . ?
C1 C2 1.446(3) . ?
C1 C8 1.461(3) . ?
C2 C3 1.372(4) . ?
C2 C4 1.501(3) . ?
C3 H3 0.90(3) . ?
C5 C6 1.500(5) . ?
C5 H51 0.96(3) . ?
C5 H52 0.96(3) . ?
C6 H61 1.00(4) . ?
C6 H62 0.99(4) . ?
C6 H63 1.02(4) . ?
C8 C13 1.403(3) . ?
C8 C9 1.410(3) . ?
C9 C10 1.351(4) . ?
C9 H9 0.98(3) . ?
C10 C11 1.411(3) . ?
C11 C12 1.380(4) . ?
C12 C13 1.408(4) . ?
C12 H12 0.90(2) . ?
C14 C15 1.520(4) . ?
C14 H141 0.99(3) . ?
C14 H142 1.05(3) . ?
C15 H151 0.94(3) . ?
C15 H152 1.08(3) . ?
C16 C17 1.511(4) . ?
C16 H161 1.02(3) . ?
C16 H162 1.05(3) . ?
C17 H171 1.01(3) . ?
C17 H172 0.95(3) . ?
O21 C21 1.359(3) . ?
O21 H21 1.05(5) . ?
N21 C28 1.481(3) . ?
N21 H27 0.98(3) . ?
N21 H28 0.95(3) . ?
N21 H29 0.97(4) . ?
C21 C26 1.378(4) . ?
C21 C22 1.382(4) . ?
C22 C23 1.373(4) . ?
C22 H22 0.97(3) . ?
C23 C24 1.379(4) . ?
C23 H23 0.94(3) . ?
C24 C25 1.373(4) . ?
C24 C27 1.515(4) . ?
C25 C26 1.381(4) . ?
C25 H25 0.87(3) . ?
C26 H26 0.87(4) . ?
C27 C28 1.514(4) . ?
C27 H271 0.97(3) . ?
C27 H272 0.93(3) . ?
C28 H281 1.05(3) . ?
C28 H282 0.98(3) . ?
O18 C18 1.370(9) . ?
O18 H18 0.8500 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O19 C19 1.367(9) . ?
O19 H19 0.8500 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C13 119.6(2) . . ?
C3 N1 C5 118.6(2) . . ?
C13 N1 C5 121.7(2) . . ?
C11 N2 C16 118.3(2) . . ?
C11 N2 C14 118.4(2) . . ?
C16 N2 C14 111.2(2) . . ?
C15 N3 C17 110.0(2) . . ?
C15 N3 H31 107.4(18) . . ?
C17 N3 H31 110.2(18) . . ?
O1 C1 C2 125.7(2) . . ?
O1 C1 C8 119.4(2) . . ?
C2 C1 C8 114.9(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C4 117.6(2) . . ?
C1 C2 C4 123.8(2) . . ?
N1 C3 C2 125.6(2) . . ?
N1 C3 H3 116.0(16) . . ?
C2 C3 H3 118.3(16) . . ?
O3 C4 O2 123.2(2) . . ?
O3 C4 C2 119.1(2) . . ?
O2 C4 C2 117.7(2) . . ?
N1 C5 C6 113.0(3) . . ?
N1 C5 H51 107.6(17) . . ?
C6 C5 H51 107.3(18) . . ?
N1 C5 H52 111.0(16) . . ?
C6 C5 H52 107.1(17) . . ?
H51 C5 H52 111(2) . . ?
C5 C6 H61 110(2) . . ?
C5 C6 H62 112(2) . . ?
H61 C6 H62 101(3) . . ?
C5 C6 H63 113(2) . . ?
H61 C6 H63 118(3) . . ?
H62 C6 H63 101(3) . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C1 123.1(2) . . ?
C9 C8 C1 119.0(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.5(14) . . ?
C8 C9 H9 120.4(14) . . ?
C9 C10 F1 117.4(2) . . ?
C9 C10 C11 123.7(2) . . ?
F1 C10 C11 118.9(2) . . ?
C12 C11 N2 123.4(2) . . ?
C12 C11 C10 116.3(2) . . ?
N2 C11 C10 120.1(2) . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 H12 115.9(14) . . ?
C13 C12 H12 122.4(14) . . ?
N1 C13 C8 118.0(2) . . ?
N1 C13 C12 121.7(2) . . ?
C8 C13 C12 120.3(2) . . ?
N2 C14 C15 109.6(2) . . ?
N2 C14 H141 105.1(17) . . ?
C15 C14 H141 111.3(18) . . ?
N2 C14 H142 105.8(14) . . ?
C15 C14 H142 112.8(15) . . ?
H141 C14 H142 112(2) . . ?
N3 C15 C14 113.4(2) . . ?
N3 C15 H151 111(2) . . ?
C14 C15 H151 107(2) . . ?
N3 C15 H152 108.5(15) . . ?
C14 C15 H152 109.2(15) . . ?
H151 C15 H152 108(3) . . ?
N2 C16 C17 109.1(2) . . ?
N2 C16 H161 110.0(16) . . ?
C17 C16 H161 103.2(17) . . ?
N2 C16 H162 114.5(15) . . ?
C17 C16 H162 110.5(14) . . ?
H161 C16 H162 109(2) . . ?
N3 C17 C16 114.5(2) . . ?
N3 C17 H171 104.2(16) . . ?
C16 C17 H171 109.4(17) . . ?
N3 C17 H172 110.4(16) . . ?
C16 C17 H172 105.5(17) . . ?
H171 C17 H172 113(2) . . ?
C21 O21 H21 106(2) . . ?
C28 N21 H27 113.0(16) . . ?
C28 N21 H28 112.5(18) . . ?
H27 N21 H28 104(2) . . ?
C28 N21 H29 109.4(19) . . ?
H27 N21 H29 103(3) . . ?
H28 N21 H29 114(3) . . ?
O21 C21 C26 123.1(3) . . ?
O21 C21 C22 118.7(3) . . ?
C26 C21 C22 118.2(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 122(2) . . ?
C21 C22 H22 117(2) . . ?
C22 C23 C24 121.6(3) . . ?
C22 C23 H23 118.2(19) . . ?
C24 C23 H23 120.0(19) . . ?
C25 C24 C23 117.0(3) . . ?
C25 C24 C27 121.7(3) . . ?
C23 C24 C27 121.3(3) . . ?
C24 C25 C26 122.4(3) . . ?
C24 C25 H25 121(2) . . ?
C26 C25 H25 116(2) . . ?
C21 C26 C25 120.0(3) . . ?
C21 C26 H26 120(2) . . ?
C25 C26 H26 120(3) . . ?
C28 C27 C24 111.5(2) . . ?
C28 C27 H271 104.3(19) . . ?
C24 C27 H271 116.8(19) . . ?
C28 C27 H272 108.5(18) . . ?
C24 C27 H272 110.0(18) . . ?
H271 C27 H272 105(2) . . ?
N21 C28 C27 110.3(2) . . ?
N21 C28 H281 108.5(15) . . ?
C27 C28 H281 110.9(15) . . ?
N21 C28 H282 108.0(15) . . ?
C27 C28 H282 113.5(15) . . ?
H281 C28 H282 105(2) . . ?
C18 O18 H18 107.8 . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 O19 H19 111.2 . . ?
O19 C19 H19A 109.5 . . ?
O19 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O19 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O1 C1 C2 C3 -176.2(3) . . . . ?
C8 C1 C2 C3 3.4(4) . . . . ?
O1 C1 C2 C4 4.1(4) . . . . ?
C8 C1 C2 C4 -176.3(2) . . . . ?
C13 N1 C3 C2 -3.1(4) . . . . ?
C5 N1 C3 C2 -178.7(3) . . . . ?
C1 C2 C3 N1 0.1(4) . . . . ?
C4 C2 C3 N1 179.8(2) . . . . ?
C3 C2 C4 O3 165.4(3) . . . . ?
C1 C2 C4 O3 -14.9(4) . . . . ?
C3 C2 C4 O2 -14.1(4) . . . . ?
C1 C2 C4 O2 165.6(2) . . . . ?
C3 N1 C5 C6 96.2(4) . . . . ?
C13 N1 C5 C6 -79.3(4) . . . . ?
O1 C1 C8 C13 175.3(2) . . . . ?
C2 C1 C8 C13 -4.3(4) . . . . ?
O1 C1 C8 C9 -5.2(4) . . . . ?
C2 C1 C8 C9 175.2(2) . . . . ?
C13 C8 C9 C10 0.0(4) . . . . ?
C1 C8 C9 C10 -179.4(2) . . . . ?
C8 C9 C10 F1 174.4(2) . . . . ?
C8 C9 C10 C11 -3.2(4) . . . . ?
C16 N2 C11 C12 9.4(4) . . . . ?
C14 N2 C11 C12 -129.9(3) . . . . ?
C16 N2 C11 C10 -165.9(3) . . . . ?
C14 N2 C11 C10 54.8(4) . . . . ?
C9 C10 C11 C12 3.2(4) . . . . ?
F1 C10 C11 C12 -174.3(2) . . . . ?
C9 C10 C11 N2 178.8(2) . . . . ?
F1 C10 C11 N2 1.3(4) . . . . ?
N2 C11 C12 C13 -175.7(2) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C3 N1 C13 C8 2.2(4) . . . . ?
C5 N1 C13 C8 177.6(2) . . . . ?
C3 N1 C13 C12 -178.5(2) . . . . ?
C5 N1 C13 C12 -3.1(4) . . . . ?
C9 C8 C13 N1 -177.9(2) . . . . ?
C1 C8 C13 N1 1.6(4) . . . . ?
C9 C8 C13 C12 2.8(4) . . . . ?
C1 C8 C13 C12 -177.7(2) . . . . ?
C11 C12 C13 N1 178.0(2) . . . . ?
C11 C12 C13 C8 -2.7(4) . . . . ?
C11 N2 C14 C15 -159.9(2) . . . . ?
C16 N2 C14 C15 58.1(3) . . . . ?
C17 N3 C15 C14 52.1(4) . . . . ?
N2 C14 C15 N3 -55.8(4) . . . . ?
C11 N2 C16 C17 160.6(2) . . . . ?
C14 N2 C16 C17 -57.4(3) . . . . ?
C15 N3 C17 C16 -52.3(4) . . . . ?
N2 C16 C17 N3 55.2(4) . . . . ?
O21 C21 C22 C23 179.5(3) . . . . ?
C26 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C22 C23 C24 C25 -1.5(5) . . . . ?
C22 C23 C24 C27 -180.0(3) . . . . ?
C23 C24 C25 C26 1.5(5) . . . . ?
C27 C24 C25 C26 180.0(3) . . . . ?
O21 C21 C26 C25 -179.5(3) . . . . ?
C22 C21 C26 C25 -0.4(5) . . . . ?
C24 C25 C26 C21 -0.6(5) . . . . ?
C25 C24 C27 C28 -97.5(4) . . . . ?
C23 C24 C27 C28 80.9(4) . . . . ?
C24 C27 C28 N21 178.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H31 O21 0.95(3) 2.23(3) 3.137(3) 158(2) 2_676
O21 H21 O2 1.05(5) 1.59(5) 2.622(3) 165(3) .
N21 H27 N3 0.98(3) 1.89(3) 2.866(4) 171(2) 1_646
N21 H28 O3 0.95(3) 1.94(3) 2.849(3) 161(3) 2_667
N21 H29 O1 0.97(4) 2.01(4) 2.818(3) 140(3) 1_545
N21 H29 O3 0.97(4) 2.07(3) 2.804(3) 131(3) 1_545

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2130548'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 F N3 O3, C8 H12 N O, H2 O'
_chemical_formula_sum            'C27 H35 F N4 O5'
_chemical_formula_weight         514.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3821(4)
_cell_length_b                   10.9262(5)
_cell_length_c                   13.5535(6)
_cell_angle_alpha                80.9238(17)
_cell_angle_beta                 79.5855(17)
_cell_angle_gamma                73.4672(18)
_cell_volume                     1301.64(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9084
_cell_measurement_theta_min      2.288
_cell_measurement_theta_max      30.566

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   0.8079
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20135
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6157
_reflns_number_gt                4384
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.1135P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6157
_refine_ls_number_parameters     474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.75853(13) 1.17046(9) 0.55221(7) 0.0558(3) Uani 1 1 d . . . . .
O1 O 0.91030(14) 0.77685(10) 0.79059(8) 0.0439(3) Uani 1 1 d . . . . .
O2 O 0.99458(14) 0.38218(10) 0.75322(9) 0.0480(3) Uani 1 1 d . . . . .
O3 O 0.97869(16) 0.51269(11) 0.86609(9) 0.0579(4) Uani 1 1 d . . . . .
N1 N 0.80540(14) 0.65860(11) 0.54757(9) 0.0332(3) Uani 1 1 d . . . . .
N2 N 0.67591(14) 1.10036(12) 0.38797(9) 0.0343(3) Uani 1 1 d . . . . .
N3 N 0.64532(14) 1.23366(11) 0.18942(9) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.88438(16) 0.73665(14) 0.71690(10) 0.0312(3) Uani 1 1 d . . . . .
C2 C 0.90271(16) 0.60365(14) 0.70601(11) 0.0327(3) Uani 1 1 d . . . . .
C3 C 0.86313(17) 0.57360(15) 0.62285(11) 0.0337(3) Uani 1 1 d . . . . .
C4 C 0.96308(17) 0.49168(15) 0.78162(12) 0.0365(4) Uani 1 1 d . . . . .
C5 C 0.7664(2) 0.61560(15) 0.46252(13) 0.0403(4) Uani 1 1 d . . . . .
C6 C 0.6917(3) 0.5095(2) 0.4815(2) 0.0654(6) Uani 1 1 d . . . . .
C7 C 0.6045(2) 0.6437(2) 0.45197(18) 0.0563(5) Uani 1 1 d . . . . .
C8 C 0.83394(16) 0.82794(14) 0.62999(10) 0.0307(3) Uani 1 1 d . . . . .
C9 C 0.82250(18) 0.95871(15) 0.62830(12) 0.0362(4) Uani 1 1 d . . . . .
C10 C 0.77270(18) 1.04358(14) 0.54943(12) 0.0373(4) Uani 1 1 d . . . . .
C11 C 0.73121(17) 1.00707(14) 0.46600(11) 0.0328(3) Uani 1 1 d . . . . .
C12 C 0.74299(17) 0.87821(15) 0.46729(12) 0.0345(3) Uani 1 1 d . . . . .
C13 C 0.79347(16) 0.78900(13) 0.54813(10) 0.0301(3) Uani 1 1 d . . . . .
C14 C 0.78410(19) 1.17092(16) 0.33281(13) 0.0378(4) Uani 1 1 d . . . . .
C15 C 0.7095(2) 1.28111(15) 0.26132(13) 0.0374(4) Uani 1 1 d . . . . .
C16 C 0.6063(2) 1.05664(17) 0.31737(13) 0.0410(4) Uani 1 1 d . . . . .
C17 C 0.5337(2) 1.17059(17) 0.24701(14) 0.0419(4) Uani 1 1 d . . . . .
C18 C 0.57486(19) 1.33763(17) 0.11610(13) 0.0425(4) Uani 1 1 d . . . . .
C19 C 0.6868(2) 1.3950(2) 0.04399(15) 0.0495(5) Uani 1 1 d . . . . .
H3 H 0.8749(16) 0.4877(15) 0.6149(11) 0.028(4) Uiso 1 1 d . . . . .
H5 H 0.839(2) 0.6199(18) 0.4004(15) 0.055(5) Uiso 1 1 d . . . . .
H9 H 0.8465(18) 0.9904(16) 0.6804(13) 0.040(4) Uiso 1 1 d . . . . .
H12 H 0.7173(19) 0.8485(16) 0.4121(14) 0.045(5) Uiso 1 1 d . . . . .
H61 H 0.726(3) 0.450(2) 0.4313(19) 0.083(7) Uiso 1 1 d . . . . .
H62 H 0.666(3) 0.476(2) 0.552(2) 0.084(7) Uiso 1 1 d . . . . .
H71 H 0.582(2) 0.669(2) 0.3818(18) 0.079(7) Uiso 1 1 d . . . . .
H72 H 0.534(2) 0.687(2) 0.5082(17) 0.066(6) Uiso 1 1 d . . . . .
H141 H 0.869(2) 1.1111(16) 0.2934(13) 0.041(4) Uiso 1 1 d . . . . .
H142 H 0.8263(19) 1.2036(16) 0.3785(13) 0.043(5) Uiso 1 1 d . . . . .
H151 H 0.6295(19) 1.3452(16) 0.3009(13) 0.040(4) Uiso 1 1 d . . . . .
H152 H 0.7854(18) 1.3209(16) 0.2269(12) 0.037(4) Uiso 1 1 d . . . . .
H161 H 0.528(2) 1.0136(17) 0.3527(14) 0.049(5) Uiso 1 1 d . . . . .
H162 H 0.6804(19) 0.9937(16) 0.2776(13) 0.037(4) Uiso 1 1 d . . . . .
H171 H 0.450(2) 1.2354(19) 0.2874(15) 0.059(6) Uiso 1 1 d . . . . .
H172 H 0.487(2) 1.1399(17) 0.2021(14) 0.048(5) Uiso 1 1 d . . . . .
H181 H 0.521(2) 1.2984(17) 0.0781(14) 0.048(5) Uiso 1 1 d . . . . .
H182 H 0.498(2) 1.4050(18) 0.1564(14) 0.051(5) Uiso 1 1 d . . . . .
H191 H 0.756(3) 1.328(2) 0.0067(16) 0.071(7) Uiso 1 1 d . . . . .
H192 H 0.635(2) 1.465(2) -0.0014(16) 0.068(6) Uiso 1 1 d . . . . .
H193 H 0.743(2) 1.4309(19) 0.0806(15) 0.060(6) Uiso 1 1 d . . . . .
O4 O 0.92401(14) 0.16369(13) 0.81524(11) 0.0608(4) Uani 1 1 d . . . . .
H4 H 0.947(3) 0.234(2) 0.7949(18) 0.076(7) Uiso 1 1 d . . . . .
N4 N 0.07215(15) 0.29687(15) 1.00460(11) 0.0382(3) Uani 1 1 d . . . . .
H41 H 0.035(2) 0.225(2) 1.0105(15) 0.058(6) Uiso 1 1 d . . . . .
H42 H 0.031(2) 0.3598(19) 0.9565(15) 0.054(5) Uiso 1 1 d . . . . .
H43 H 0.048(2) 0.331(2) 1.0680(17) 0.063(6) Uiso 1 1 d . . . . .
C21 C 0.46320(19) 0.20291(17) 0.85530(12) 0.0437(4) Uani 1 1 d . . . . .
C22 C 0.5659(2) 0.08779(18) 0.88027(14) 0.0485(4) Uani 1 1 d . . . . .
C23 C 0.7174(2) 0.07623(17) 0.86653(14) 0.0495(4) Uani 1 1 d . . . . .
C24 C 0.77265(19) 0.18079(15) 0.82687(12) 0.0426(4) Uani 1 1 d . . . . .
C25 C 0.6732(2) 0.29637(17) 0.79906(13) 0.0467(4) Uani 1 1 d . . . . .
C26 C 0.5212(2) 0.30630(18) 0.81399(14) 0.0488(4) Uani 1 1 d . . . . .
C27 C 0.2966(2) 0.2178(2) 0.87890(15) 0.0533(5) Uani 1 1 d . . . . .
C28 C 0.23750(18) 0.26494(17) 0.98079(12) 0.0382(4) Uani 1 1 d . . . . .
H22 H 0.529(2) 0.014(2) 0.9074(16) 0.071(6) Uiso 1 1 d . . . . .
H23 H 0.786(2) -0.005(2) 0.8785(15) 0.059(5) Uiso 1 1 d . . . . .
H25 H 0.709(2) 0.368(2) 0.7726(15) 0.059(6) Uiso 1 1 d . . . . .
H26 H 0.453(2) 0.3878(19) 0.7959(14) 0.055(5) Uiso 1 1 d . . . . .
H271 H 0.271(3) 0.139(2) 0.8775(18) 0.080(7) Uiso 1 1 d . . . . .
H272 H 0.245(3) 0.281(2) 0.8310(18) 0.077(7) Uiso 1 1 d . . . . .
H281 H 0.2645(18) 0.3444(17) 0.9824(12) 0.039(4) Uiso 1 1 d . . . . .
H282 H 0.278(2) 0.1996(18) 1.0321(14) 0.052(5) Uiso 1 1 d . . . . .
O5 O 0.91525(18) 1.09198(16) 0.06787(11) 0.0635(4) Uani 1 1 d . . . . .
H51 H 0.824(4) 1.129(3) 0.112(2) 0.115(10) Uiso 1 1 d . . . . .
H52 H 0.937(4) 1.006(4) 0.095(3) 0.154(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
F1 C10 1.3604(17) . ?
O1 C1 1.2395(18) . ?
O2 C4 1.253(2) . ?
O3 C4 1.2440(19) . ?
N1 C3 1.3458(18) . ?
N1 C13 1.3981(18) . ?
N1 C5 1.451(2) . ?
N2 C11 1.4085(17) . ?
N2 C16 1.455(2) . ?
N2 C14 1.474(2) . ?
N3 C17 1.458(2) . ?
N3 C15 1.459(2) . ?
N3 C18 1.4728(18) . ?
C1 C2 1.442(2) . ?
C1 C8 1.4727(19) . ?
C2 C3 1.362(2) . ?
C2 C4 1.512(2) . ?
C3 H3 0.934(15) . ?
C5 C6 1.485(3) . ?
C5 C7 1.490(3) . ?
C5 H5 0.98(2) . ?
C6 C7 1.493(3) . ?
C6 H61 0.96(2) . ?
C6 H62 0.98(3) . ?
C7 H71 0.99(2) . ?
C7 H72 1.00(2) . ?
C8 C13 1.396(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.357(2) . ?
C9 H9 0.921(18) . ?
C10 C11 1.407(2) . ?
C11 C12 1.378(2) . ?
C12 C13 1.401(2) . ?
C12 H12 0.953(18) . ?
C14 C15 1.509(2) . ?
C14 H141 1.004(18) . ?
C14 H142 0.952(18) . ?
C15 H151 1.007(17) . ?
C15 H152 0.951(17) . ?
C16 C17 1.517(2) . ?
C16 H161 0.995(19) . ?
C16 H162 0.978(17) . ?
C17 H171 1.04(2) . ?
C17 H172 0.960(19) . ?
C18 C19 1.503(3) . ?
C18 H181 0.997(19) . ?
C18 H182 1.022(19) . ?
C19 H191 0.97(2) . ?
C19 H192 0.97(2) . ?
C19 H193 0.98(2) . ?
O4 C24 1.362(2) . ?
O4 H4 0.85(3) . ?
N4 C28 1.476(2) . ?
N4 H41 0.93(2) . ?
N4 H42 0.92(2) . ?
N4 H43 0.96(2) . ?
C21 C22 1.385(2) . ?
C21 C26 1.388(3) . ?
C21 C27 1.504(3) . ?
C22 C23 1.372(3) . ?
C22 H22 0.97(2) . ?
C23 C24 1.380(2) . ?
C23 H23 0.94(2) . ?
C24 C25 1.384(2) . ?
C25 C26 1.379(3) . ?
C25 H25 0.93(2) . ?
C26 H26 0.96(2) . ?
C27 C28 1.505(3) . ?
C27 H271 0.96(2) . ?
C27 H272 0.95(2) . ?
C28 H281 0.976(18) . ?
C28 H282 0.958(19) . ?
O5 H51 0.98(3) . ?
O5 H52 0.93(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C13 119.22(12) . . ?
C3 N1 C5 120.83(12) . . ?
C13 N1 C5 119.78(11) . . ?
C11 N2 C16 115.59(12) . . ?
C11 N2 C14 114.40(12) . . ?
C16 N2 C14 110.30(12) . . ?
C17 N3 C15 107.53(12) . . ?
C17 N3 C18 109.94(12) . . ?
C15 N3 C18 112.18(12) . . ?
O1 C1 C2 125.48(12) . . ?
O1 C1 C8 119.73(13) . . ?
C2 C1 C8 114.77(13) . . ?
C3 C2 C1 119.20(13) . . ?
C3 C2 C4 116.14(13) . . ?
C1 C2 C4 124.65(13) . . ?
N1 C3 C2 125.54(14) . . ?
N1 C3 H3 114.5(9) . . ?
C2 C3 H3 119.9(9) . . ?
O3 C4 O2 124.45(14) . . ?
O3 C4 C2 119.34(14) . . ?
O2 C4 C2 116.21(14) . . ?
N1 C5 C6 118.87(16) . . ?
N1 C5 C7 118.37(15) . . ?
C6 C5 C7 60.25(14) . . ?
N1 C5 H5 113.8(11) . . ?
C6 C5 H5 117.9(11) . . ?
C7 C5 H5 117.7(11) . . ?
C5 C6 C7 60.07(13) . . ?
C5 C6 H61 113.7(15) . . ?
C7 C6 H61 119.0(15) . . ?
C5 C6 H62 117.1(15) . . ?
C7 C6 H62 114.7(14) . . ?
H61 C6 H62 119(2) . . ?
C5 C7 C6 59.68(13) . . ?
C5 C7 H71 114.9(13) . . ?
C6 C7 H71 119.1(13) . . ?
C5 C7 H72 114.5(12) . . ?
C6 C7 H72 114.6(12) . . ?
H71 C7 H72 119.7(18) . . ?
C13 C8 C9 117.73(12) . . ?
C13 C8 C1 122.08(13) . . ?
C9 C8 C1 120.18(13) . . ?
C10 C9 C8 120.36(14) . . ?
C10 C9 H9 117.8(10) . . ?
C8 C9 H9 121.8(10) . . ?
C9 C10 F1 118.54(14) . . ?
C9 C10 C11 123.13(14) . . ?
F1 C10 C11 118.30(12) . . ?
C12 C11 C10 116.61(13) . . ?
C12 C11 N2 122.96(13) . . ?
C10 C11 N2 120.39(13) . . ?
C11 C12 C13 121.22(14) . . ?
C11 C12 H12 119.8(10) . . ?
C13 C12 H12 119.0(10) . . ?
C8 C13 N1 118.80(12) . . ?
C8 C13 C12 120.94(13) . . ?
N1 C13 C12 120.25(13) . . ?
N2 C14 C15 110.89(13) . . ?
N2 C14 H141 109.6(10) . . ?
C15 C14 H141 109.2(10) . . ?
N2 C14 H142 110.8(10) . . ?
C15 C14 H142 109.0(10) . . ?
H141 C14 H142 107.2(14) . . ?
N3 C15 C14 110.23(13) . . ?
N3 C15 H151 110.7(10) . . ?
C14 C15 H151 109.6(9) . . ?
N3 C15 H152 110.3(10) . . ?
C14 C15 H152 106.7(10) . . ?
H151 C15 H152 109.1(13) . . ?
N2 C16 C17 109.53(14) . . ?
N2 C16 H161 111.9(10) . . ?
C17 C16 H161 108.5(10) . . ?
N2 C16 H162 111.0(10) . . ?
C17 C16 H162 109.4(10) . . ?
H161 C16 H162 106.4(14) . . ?
N3 C17 C16 110.80(13) . . ?
N3 C17 H171 110.2(11) . . ?
C16 C17 H171 110.5(11) . . ?
N3 C17 H172 110.1(11) . . ?
C16 C17 H172 108.1(11) . . ?
H171 C17 H172 107.0(15) . . ?
N3 C18 C19 113.01(14) . . ?
N3 C18 H181 106.0(10) . . ?
C19 C18 H181 109.9(11) . . ?
N3 C18 H182 107.2(10) . . ?
C19 C18 H182 111.7(11) . . ?
H181 C18 H182 108.8(15) . . ?
C18 C19 H191 108.8(13) . . ?
C18 C19 H192 110.0(12) . . ?
H191 C19 H192 110.9(17) . . ?
C18 C19 H193 110.7(12) . . ?
H191 C19 H193 108.9(18) . . ?
H192 C19 H193 107.5(17) . . ?
C24 O4 H4 110.9(16) . . ?
C28 N4 H41 112.4(12) . . ?
C28 N4 H42 109.3(12) . . ?
H41 N4 H42 111.5(18) . . ?
C28 N4 H43 105.6(12) . . ?
H41 N4 H43 109.4(18) . . ?
H42 N4 H43 108.5(17) . . ?
C22 C21 C26 116.74(16) . . ?
C22 C21 C27 121.62(18) . . ?
C26 C21 C27 121.49(17) . . ?
C23 C22 C21 121.99(18) . . ?
C23 C22 H22 119.4(13) . . ?
C21 C22 H22 118.6(13) . . ?
C22 C23 C24 120.39(16) . . ?
C22 C23 H23 120.6(12) . . ?
C24 C23 H23 118.8(12) . . ?
O4 C24 C23 117.78(15) . . ?
O4 C24 C25 123.24(16) . . ?
C23 C24 C25 118.96(17) . . ?
C26 C25 C24 119.78(18) . . ?
C26 C25 H25 120.2(12) . . ?
C24 C25 H25 119.9(12) . . ?
C25 C26 C21 122.12(16) . . ?
C25 C26 H26 118.9(12) . . ?
C21 C26 H26 119.0(12) . . ?
C21 C27 C28 110.06(15) . . ?
C21 C27 H271 112.4(14) . . ?
C28 C27 H271 109.5(14) . . ?
C21 C27 H272 110.7(14) . . ?
C28 C27 H272 106.7(14) . . ?
H271 C27 H272 107(2) . . ?
N4 C28 C27 113.50(14) . . ?
N4 C28 H281 105.6(9) . . ?
C27 C28 H281 109.4(10) . . ?
N4 C28 H282 107.5(11) . . ?
C27 C28 H282 109.3(11) . . ?
H281 C28 H282 111.5(15) . . ?
H51 O5 H52 102(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 176.91(14) . . . . ?
C8 C1 C2 C3 -4.6(2) . . . . ?
O1 C1 C2 C4 -2.7(2) . . . . ?
C8 C1 C2 C4 175.73(13) . . . . ?
C13 N1 C3 C2 5.1(2) . . . . ?
C5 N1 C3 C2 -179.67(15) . . . . ?
C1 C2 C3 N1 -0.6(2) . . . . ?
C4 C2 C3 N1 179.04(14) . . . . ?
C3 C2 C4 O3 -168.61(15) . . . . ?
C1 C2 C4 O3 11.0(2) . . . . ?
C3 C2 C4 O2 11.6(2) . . . . ?
C1 C2 C4 O2 -168.79(14) . . . . ?
C3 N1 C5 C6 41.1(2) . . . . ?
C13 N1 C5 C6 -143.61(17) . . . . ?
C3 N1 C5 C7 110.89(17) . . . . ?
C13 N1 C5 C7 -73.9(2) . . . . ?
N1 C5 C6 C7 108.05(18) . . . . ?
N1 C5 C7 C6 -108.87(19) . . . . ?
O1 C1 C8 C13 -175.59(13) . . . . ?
C2 C1 C8 C13 5.9(2) . . . . ?
O1 C1 C8 C9 3.2(2) . . . . ?
C2 C1 C8 C9 -175.36(14) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
C1 C8 C9 C10 -178.45(14) . . . . ?
C8 C9 C10 F1 177.88(14) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
F1 C10 C11 C12 -178.16(14) . . . . ?
C9 C10 C11 N2 178.01(15) . . . . ?
F1 C10 C11 N2 -0.3(2) . . . . ?
C16 N2 C11 C12 10.6(2) . . . . ?
C14 N2 C11 C12 -119.14(17) . . . . ?
C16 N2 C11 C10 -167.11(15) . . . . ?
C14 N2 C11 C10 63.11(19) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
N2 C11 C12 C13 -177.66(14) . . . . ?
C9 C8 C13 N1 179.35(13) . . . . ?
C1 C8 C13 N1 -1.8(2) . . . . ?
C9 C8 C13 C12 -0.1(2) . . . . ?
C1 C8 C13 C12 178.71(14) . . . . ?
C3 N1 C13 C8 -3.6(2) . . . . ?
C5 N1 C13 C8 -178.95(13) . . . . ?
C3 N1 C13 C12 175.81(14) . . . . ?
C5 N1 C13 C12 0.5(2) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C11 C12 C13 N1 -179.62(14) . . . . ?
C11 N2 C14 C15 -171.78(14) . . . . ?
C16 N2 C14 C15 55.88(18) . . . . ?
C17 N3 C15 C14 60.63(17) . . . . ?
C18 N3 C15 C14 -178.37(14) . . . . ?
N2 C14 C15 N3 -58.54(19) . . . . ?
C11 N2 C16 C17 172.28(14) . . . . ?
C14 N2 C16 C17 -55.99(19) . . . . ?
C15 N3 C17 C16 -61.95(18) . . . . ?
C18 N3 C17 C16 175.65(15) . . . . ?
N2 C16 C17 N3 60.4(2) . . . . ?
C17 N3 C18 C19 -171.90(16) . . . . ?
C15 N3 C18 C19 68.5(2) . . . . ?
C26 C21 C22 C23 1.0(3) . . . . ?
C27 C21 C22 C23 -174.59(17) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 O4 179.79(17) . . . . ?
C22 C23 C24 C25 -1.5(3) . . . . ?
O4 C24 C25 C26 -179.50(17) . . . . ?
C23 C24 C25 C26 1.9(3) . . . . ?
C24 C25 C26 C21 -0.8(3) . . . . ?
C22 C21 C26 C25 -0.6(3) . . . . ?
C27 C21 C26 C25 174.99(16) . . . . ?
C22 C21 C27 C28 91.4(2) . . . . ?
C26 C21 C27 C28 -84.0(2) . . . . ?
C21 C27 C28 N4 173.13(16) . . . . ?

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
O4 H4 O2 0.85(3) 1.78(3) 2.6286(19) 179(2) .
N4 H41 O5 0.93(2) 2.06(2) 2.954(2) 160.5(17) 1_446
N4 H42 O3 0.92(2) 1.91(2) 2.8063(17) 165.1(18) 1_455
N4 H43 O1 0.96(2) 2.12(2) 2.7867(18) 125.1(16) 2_667
N4 H43 O3 0.96(2) 1.98(2) 2.813(2) 144.4(18) 2_667
O5 H51 N3 0.98(3) 1.96(3) 2.931(2) 170(3) .
O5 H52 O4 0.93(4) 2.27(4) 3.108(2) 151(3) 2_766

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.039



