# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1993397'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-03-29 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 F N3 O3, C7 H6 N O2, H2 O'
_chemical_formula_sum            'C24 H27 F N4 O6'
_chemical_formula_weight         486.50

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   21.457(2)
_cell_length_b                   14.4489(15)
_cell_length_c                   7.3700(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.013(2)
_cell_angle_gamma                90.00
_cell_volume                     2284.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4486
_cell_measurement_theta_min      2.365
_cell_measurement_theta_max      30.250

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23168
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         28.00
_reflns_number_total             5512
_reflns_number_gt                4282
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0566P)²+1.5604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5512
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.67470(5) 0.82983(7) 0.18556(14) 0.0207(2) Uani 1 1 d . . .
O1 O 0.89199(6) 0.91164(9) 0.37118(18) 0.0241(3) Uani 1 1 d . . .
O2 O 1.04069(6) 0.76275(10) 0.5693(2) 0.0303(3) Uani 1 1 d . . .
O3 O 1.00075(6) 0.90043(9) 0.5089(2) 0.0285(3) Uani 1 1 d . . .
H33 H 0.9629(14) 0.9221(19) 0.458(4) 0.049(8) Uiso 1 1 d . . .
N1 N 0.87823(7) 0.62930(10) 0.4125(2) 0.0173(3) Uani 1 1 d . . .
N2 N 0.65794(6) 0.64505(10) 0.24912(19) 0.0175(3) Uani 1 1 d . . .
N3 N 0.54580(7) 0.54594(11) 0.1762(2) 0.0204(3) Uani 1 1 d . . .
H31 H 0.5018(14) 0.5409(19) 0.187(4) 0.049(7) Uiso 1 1 d . . .
H32 H 0.5590(11) 0.5020(17) 0.103(3) 0.034(6) Uiso 1 1 d . . .
C1 C 0.88768(8) 0.82523(12) 0.3860(2) 0.0179(3) Uani 1 1 d . . .
C2 C 0.93749(8) 0.76811(12) 0.4520(2) 0.0187(3) Uani 1 1 d . . .
C3 C 0.93038(8) 0.67430(12) 0.4605(2) 0.0184(3) Uani 1 1 d . . .
C4 C 0.99740(8) 0.80877(13) 0.5137(2) 0.0219(4) Uani 1 1 d . . .
C5 C 0.87491(8) 0.52916(12) 0.4356(3) 0.0192(4) Uani 1 1 d . . .
C6 C 0.92846(9) 0.47215(14) 0.3684(3) 0.0270(4) Uani 1 1 d . . .
C7 C 0.86708(9) 0.46993(14) 0.2699(3) 0.0264(4) Uani 1 1 d . . .
C8 C 0.83089(8) 0.77598(12) 0.3382(2) 0.0168(3) Uani 1 1 d . . .
C9 C 0.77874(8) 0.82553(13) 0.2772(2) 0.0181(3) Uani 1 1 d . . .
C10 C 0.72487(8) 0.78009(12) 0.2400(2) 0.0170(3) Uani 1 1 d . . .
C11 C 0.71725(8) 0.68364(12) 0.2659(2) 0.0168(3) Uani 1 1 d . . .
C12 C 0.76918(8) 0.63425(12) 0.3216(2) 0.0174(3) Uani 1 1 d . . .
C13 C 0.82594(8) 0.67966(12) 0.3559(2) 0.0162(3) Uani 1 1 d . . .
C14 C 0.62736(8) 0.65271(13) 0.0701(2) 0.0190(3) Uani 1 1 d . . .
C15 C 0.55819(8) 0.63698(13) 0.0876(3) 0.0217(4) Uani 1 1 d . . .
C16 C 0.64683(8) 0.55422(12) 0.3310(3) 0.0196(4) Uani 1 1 d . . .
C17 C 0.57721(8) 0.54103(13) 0.3558(2) 0.0209(4) Uani 1 1 d . . .
H3 H 0.9612(10) 0.6367(14) 0.504(3) 0.018(5) Uiso 1 1 d . . .
H5 H 0.8577(9) 0.5146(13) 0.548(3) 0.013(5) Uiso 1 1 d . . .
H9 H 0.7798(11) 0.8835(17) 0.269(3) 0.030(6) Uiso 1 1 d . . .
H12 H 0.7659(10) 0.5646(16) 0.338(3) 0.027(6) Uiso 1 1 d . . .
H61 H 0.9628(12) 0.5045(17) 0.304(3) 0.036(6) Uiso 1 1 d . . .
H62 H 0.9402(10) 0.4189(16) 0.442(3) 0.027(6) Uiso 1 1 d . . .
H71 H 0.8655(11) 0.5026(16) 0.151(3) 0.031(6) Uiso 1 1 d . . .
H72 H 0.8382(11) 0.4136(17) 0.286(3) 0.031(6) Uiso 1 1 d . . .
H141 H 0.6453(10) 0.6056(15) -0.010(3) 0.022(5) Uiso 1 1 d . . .
H142 H 0.6329(9) 0.7133(14) 0.020(3) 0.016(5) Uiso 1 1 d . . .
H151 H 0.5392(10) 0.6875(15) 0.166(3) 0.023(5) Uiso 1 1 d . . .
H152 H 0.5388(10) 0.6373(15) -0.029(3) 0.026(5) Uiso 1 1 d . . .
H161 H 0.6640(11) 0.5058(17) 0.253(3) 0.035(6) Uiso 1 1 d . . .
H162 H 0.6661(10) 0.5541(14) 0.451(3) 0.019(5) Uiso 1 1 d . . .
H171 H 0.5610(10) 0.5873(16) 0.430(3) 0.025(6) Uiso 1 1 d . . .
H172 H 0.5674(11) 0.4823(17) 0.410(3) 0.034(6) Uiso 1 1 d . . .
N21 N 0.14061(8) 0.66906(15) 0.3343(3) 0.0358(4) Uani 1 1 d . . .
H21 H 0.1292(12) 0.713(2) 0.416(4) 0.043(7) Uiso 1 1 d . . .
H22 H 0.1187(13) 0.6588(18) 0.238(4) 0.042(7) Uiso 1 1 d . . .
O21 O 0.43815(6) 0.64960(9) 0.36725(18) 0.0254(3) Uani 1 1 d . . .
O22 O 0.41982(6) 0.53957(10) 0.16312(18) 0.0266(3) Uani 1 1 d . . .
C21 C 0.40150(8) 0.60171(12) 0.2717(2) 0.0206(4) Uani 1 1 d . . .
C22 C 0.33269(8) 0.61755(12) 0.2891(2) 0.0207(4) Uani 1 1 d . . .
C23 C 0.30924(10) 0.67542(15) 0.4239(3) 0.0295(4) Uani 1 1 d . . .
C24 C 0.24626(10) 0.69104(16) 0.4406(3) 0.0330(5) Uani 1 1 d . . .
C25 C 0.20376(9) 0.65158(13) 0.3198(3) 0.0249(4) Uani 1 1 d . . .
C26 C 0.22689(9) 0.59178(14) 0.1868(3) 0.0271(4) Uani 1 1 d . . .
C27 C 0.29039(9) 0.57593(13) 0.1729(3) 0.0251(4) Uani 1 1 d . . .
H23 H 0.3351(12) 0.7040(18) 0.513(3) 0.039(7) Uiso 1 1 d . . .
H24 H 0.2316(13) 0.732(2) 0.534(4) 0.052(8) Uiso 1 1 d . . .
H26 H 0.2001(12) 0.5637(18) 0.102(3) 0.039(7) Uiso 1 1 d . . .
H27 H 0.3044(11) 0.5353(17) 0.080(3) 0.036(6) Uiso 1 1 d . . .
O10 O 0.45498(10) 0.66491(12) 0.7489(3) 0.0490(5) Uani 1 1 d . . .
H10 H 0.4503(14) 0.674(2) 0.629(4) 0.055(8) Uiso 1 1 d . . .
H11 H 0.4476(14) 0.717(2) 0.795(4) 0.057(9) 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 1.3551(18) . ?
O1 C1 1.257(2) . ?
O2 C4 1.214(2) . ?
O3 C4 1.327(2) . ?
O3 H33 0.95(3) . ?
N1 C3 1.341(2) . ?
N1 C13 1.401(2) . ?
N1 C5 1.459(2) . ?
N2 C11 1.395(2) . ?
N2 C16 1.464(2) . ?
N2 C14 1.477(2) . ?
N3 C17 1.487(2) . ?
N3 C15 1.493(2) . ?
N3 H31 0.95(3) . ?
N3 H32 0.88(3) . ?
C1 C2 1.435(2) . ?
C1 C8 1.454(2) . ?
C2 C3 1.365(2) . ?
C2 C4 1.485(2) . ?
C3 H3 0.91(2) . ?
C5 C6 1.498(3) . ?
C5 C7 1.500(3) . ?
C5 H5 0.93(2) . ?
C6 C7 1.504(3) . ?
C6 H61 0.99(3) . ?
C6 H62 0.98(2) . ?
C7 H71 1.00(2) . ?
C7 H72 1.03(2) . ?
C8 C13 1.402(2) . ?
C8 C9 1.402(2) . ?
C9 C10 1.357(2) . ?
C9 H9 0.84(2) . ?
C10 C11 1.416(2) . ?
C11 C12 1.385(2) . ?
C12 C13 1.406(2) . ?
C12 H12 1.02(2) . ?
C14 C15 1.507(2) . ?
C14 H141 0.98(2) . ?
C14 H142 0.96(2) . ?
C15 H151 1.01(2) . ?
C15 H152 0.96(2) . ?
C16 C17 1.517(2) . ?
C16 H161 0.98(2) . ?
C16 H162 0.97(2) . ?
C17 H171 0.93(2) . ?
C17 H172 0.96(3) . ?
N21 C25 1.382(3) . ?
N21 H21 0.91(3) . ?
N21 H22 0.86(3) . ?
O21 C21 1.262(2) . ?
O22 C21 1.265(2) . ?
C21 C22 1.500(2) . ?
C22 C27 1.385(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.376(3) . ?
C23 H23 0.95(3) . ?
C24 C25 1.396(3) . ?
C24 H24 0.96(3) . ?
C25 C26 1.398(3) . ?
C26 C27 1.385(3) . ?
C26 H26 0.94(3) . ?
C27 H27 0.95(3) . ?
O10 H10 0.90(3) . ?
O10 H11 0.84(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
C4 O3 H33 107.1(17) . . ?
C3 N1 C13 119.66(14) . . ?
C3 N1 C5 119.39(14) . . ?
C13 N1 C5 120.72(14) . . ?
C11 N2 C16 118.06(14) . . ?
C11 N2 C14 117.02(14) . . ?
C16 N2 C14 111.29(14) . . ?
C17 N3 C15 110.54(14) . . ?
C17 N3 H31 111.7(16) . . ?
C15 N3 H31 106.4(17) . . ?
C17 N3 H32 111.3(16) . . ?
C15 N3 H32 108.1(16) . . ?
H31 N3 H32 109(2) . . ?
O1 C1 C2 123.08(16) . . ?
O1 C1 C8 121.79(16) . . ?
C2 C1 C8 115.12(15) . . ?
C3 C2 C1 120.21(16) . . ?
C3 C2 C4 118.40(16) . . ?
C1 C2 C4 121.39(16) . . ?
N1 C3 C2 124.21(16) . . ?
N1 C3 H3 114.1(13) . . ?
C2 C3 H3 121.7(13) . . ?
O2 C4 O3 120.96(17) . . ?
O2 C4 C2 123.31(17) . . ?
O3 C4 C2 115.71(16) . . ?
N1 C5 C6 118.00(16) . . ?
N1 C5 C7 118.45(16) . . ?
C6 C5 C7 60.20(13) . . ?
N1 C5 H5 110.3(12) . . ?
C6 C5 H5 118.3(12) . . ?
C7 C5 H5 123.4(12) . . ?
C5 C6 C7 59.98(13) . . ?
C5 C6 H61 117.9(14) . . ?
C7 C6 H61 115.6(14) . . ?
C5 C6 H62 116.6(13) . . ?
C7 C6 H62 118.6(13) . . ?
H61 C6 H62 116.4(19) . . ?
C5 C7 C6 59.82(12) . . ?
C5 C7 H71 116.8(14) . . ?
C6 C7 H71 116.4(14) . . ?
C5 C7 H72 115.2(13) . . ?
C6 C7 H72 119.3(13) . . ?
H71 C7 H72 116.9(19) . . ?
C13 C8 C9 118.45(15) . . ?
C13 C8 C1 121.78(15) . . ?
C9 C8 C1 119.75(15) . . ?
C10 C9 C8 119.81(16) . . ?
C10 C9 H9 119.4(16) . . ?
C8 C9 H9 120.7(16) . . ?
F1 C10 C9 118.66(15) . . ?
F1 C10 C11 118.04(14) . . ?
C9 C10 C11 123.18(16) . . ?
C12 C11 N2 123.65(16) . . ?
C12 C11 C10 117.00(15) . . ?
N2 C11 C10 119.14(15) . . ?
C11 C12 C13 120.62(16) . . ?
C11 C12 H12 119.2(13) . . ?
C13 C12 H12 120.1(12) . . ?
N1 C13 C8 118.87(15) . . ?
N1 C13 C12 120.32(15) . . ?
C8 C13 C12 120.80(15) . . ?
N2 C14 C15 110.46(14) . . ?
N2 C14 H141 108.2(12) . . ?
C15 C14 H141 109.4(12) . . ?
N2 C14 H142 110.9(12) . . ?
C15 C14 H142 107.1(12) . . ?
H141 C14 H142 110.7(17) . . ?
N3 C15 C14 110.23(15) . . ?
N3 C15 H151 108.3(12) . . ?
C14 C15 H151 109.6(12) . . ?
N3 C15 H152 108.7(13) . . ?
C14 C15 H152 110.5(13) . . ?
H151 C15 H152 109.4(18) . . ?
N2 C16 C17 108.83(14) . . ?
N2 C16 H161 109.8(14) . . ?
C17 C16 H161 110.6(14) . . ?
N2 C16 H162 107.8(12) . . ?
C17 C16 H162 108.0(12) . . ?
H161 C16 H162 111.8(18) . . ?
N3 C17 C16 109.45(15) . . ?
N3 C17 H171 108.7(13) . . ?
C16 C17 H171 110.4(14) . . ?
N3 C17 H172 108.4(14) . . ?
C16 C17 H172 112.1(14) . . ?
H171 C17 H172 107.7(19) . . ?
C25 N21 H21 116.4(17) . . ?
C25 N21 H22 116.1(18) . . ?
H21 N21 H22 121(2) . . ?
O21 C21 O22 123.24(17) . . ?
O21 C21 C22 118.83(16) . . ?
O22 C21 C22 117.92(16) . . ?
C27 C22 C23 117.71(17) . . ?
C27 C22 C21 121.75(16) . . ?
C23 C22 C21 120.55(17) . . ?
C24 C23 C22 121.17(19) . . ?
C24 C23 H23 116.1(15) . . ?
C22 C23 H23 122.7(15) . . ?
C23 C24 C25 121.14(19) . . ?
C23 C24 H24 119.1(17) . . ?
C25 C24 H24 119.7(17) . . ?
N21 C25 C24 121.06(19) . . ?
N21 C25 C26 121.0(2) . . ?
C24 C25 C26 117.88(18) . . ?
C27 C26 C25 120.22(18) . . ?
C27 C26 H26 118.9(16) . . ?
C25 C26 H26 120.9(16) . . ?
C22 C27 C26 121.80(18) . . ?
C22 C27 H27 120.4(15) . . ?
C26 C27 H27 117.8(15) . . ?
H10 O10 H11 104(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 -178.35(17) . . . . ?
C8 C1 C2 C3 2.2(2) . . . . ?
O1 C1 C2 C4 2.1(3) . . . . ?
C8 C1 C2 C4 -177.33(15) . . . . ?
C13 N1 C3 C2 -2.6(3) . . . . ?
C5 N1 C3 C2 -177.07(17) . . . . ?
C1 C2 C3 N1 -0.9(3) . . . . ?
C4 C2 C3 N1 178.59(16) . . . . ?
C3 C2 C4 O2 0.9(3) . . . . ?
C1 C2 C4 O2 -179.55(17) . . . . ?
C3 C2 C4 O3 -177.47(16) . . . . ?
C1 C2 C4 O3 2.1(2) . . . . ?
C3 N1 C5 C6 -47.8(2) . . . . ?
C13 N1 C5 C6 137.72(17) . . . . ?
C3 N1 C5 C7 -117.23(18) . . . . ?
C13 N1 C5 C7 68.3(2) . . . . ?
N1 C5 C6 C7 -108.50(18) . . . . ?
N1 C5 C7 C6 107.76(18) . . . . ?
O1 C1 C8 C13 -179.55(16) . . . . ?
C2 C1 C8 C13 -0.1(2) . . . . ?
O1 C1 C8 C9 -1.3(3) . . . . ?
C2 C1 C8 C9 178.14(15) . . . . ?
C13 C8 C9 C10 1.1(2) . . . . ?
C1 C8 C9 C10 -177.17(16) . . . . ?
C8 C9 C10 F1 178.42(14) . . . . ?
C8 C9 C10 C11 2.4(3) . . . . ?
C16 N2 C11 C12 13.8(2) . . . . ?
C14 N2 C11 C12 -123.42(18) . . . . ?
C16 N2 C11 C10 -160.70(15) . . . . ?
C14 N2 C11 C10 62.1(2) . . . . ?
F1 C10 C11 C12 180.00(14) . . . . ?
C9 C10 C11 C12 -4.0(3) . . . . ?
F1 C10 C11 N2 -5.2(2) . . . . ?
C9 C10 C11 N2 170.85(16) . . . . ?
N2 C11 C12 C13 -172.57(15) . . . . ?
C10 C11 C12 C13 2.0(2) . . . . ?
C3 N1 C13 C8 4.6(2) . . . . ?
C5 N1 C13 C8 179.00(15) . . . . ?
C3 N1 C13 C12 -173.96(16) . . . . ?
C5 N1 C13 C12 0.5(2) . . . . ?
C9 C8 C13 N1 178.50(15) . . . . ?
C1 C8 C13 N1 -3.3(2) . . . . ?
C9 C8 C13 C12 -3.0(2) . . . . ?
C1 C8 C13 C12 175.28(15) . . . . ?
C11 C12 C13 N1 179.87(15) . . . . ?
C11 C12 C13 C8 1.4(2) . . . . ?
C11 N2 C14 C15 -161.69(15) . . . . ?
C16 N2 C14 C15 58.37(19) . . . . ?
C17 N3 C15 C14 56.6(2) . . . . ?
N2 C14 C15 N3 -55.4(2) . . . . ?
C11 N2 C16 C17 160.26(15) . . . . ?
C14 N2 C16 C17 -60.26(18) . . . . ?
C15 N3 C17 C16 -58.9(2) . . . . ?
N2 C16 C17 N3 60.20(19) . . . . ?
O21 C21 C22 C27 171.84(17) . . . . ?
O22 C21 C22 C27 -9.2(3) . . . . ?
O21 C21 C22 C23 -8.0(3) . . . . ?
O22 C21 C22 C23 170.96(18) . . . . ?
C27 C22 C23 C24 -0.3(3) . . . . ?
C21 C22 C23 C24 179.58(19) . . . . ?
C22 C23 C24 C25 -1.9(3) . . . . ?
C23 C24 C25 N21 -178.5(2) . . . . ?
C23 C24 C25 C26 3.3(3) . . . . ?
N21 C25 C26 C27 179.23(19) . . . . ?
C24 C25 C26 C27 -2.5(3) . . . . ?
C23 C22 C27 C26 1.0(3) . . . . ?
C21 C22 C27 C26 -178.85(18) . . . . ?
C25 C26 C27 C22 0.4(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
O3 H33 O1 0.95(3) 1.66(3) 2.5497(19) 155(3) .
N3 H31 O22 0.95(3) 1.77(3) 2.706(2) 169(2) .
N3 H32 O22 0.88(3) 2.10(3) 2.886(2) 148(2) 3_665
N21 H21 O2 0.91(3) 2.32(3) 3.071(2) 139(2) 1_455
N21 H22 O2 0.86(3) 2.37(3) 3.062(2) 137(2) 4_475
O10 H10 O21 0.90(3) 1.98(3) 2.844(2) 162(3) .
O10 H11 O21 0.84(3) 2.01(4) 2.842(2) 170(3) 4_576

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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 1993399'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-03-29 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_vrf_PLAT355_a                   
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O3       - H30      .       1.10 Ang.  
RESPONSE: This is a result of strong hydrogen bonding between atoms
O3 and O1 - 2.5149(16) A
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 F N3 O3, C7 H5 O3, H2 O'
_chemical_formula_sum            'C24 H26 F N3 O7'
_chemical_formula_weight         487.48

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'

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

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

_cell_length_a                   7.1977(13)
_cell_length_b                   9.9766(18)
_cell_length_c                   16.836(3)
_cell_angle_alpha                81.999(3)
_cell_angle_beta                 80.626(3)
_cell_angle_gamma                72.472(3)
_cell_volume                     1132.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3895
_cell_measurement_theta_min      2.374
_cell_measurement_theta_max      30.543

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12642
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         29.00
_reflns_number_total             5996
_reflns_number_gt                4671
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.2378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5996
_refine_ls_number_parameters     420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.65870(13) 0.96824(8) 0.43240(5) 0.0336(2) Uani 1 1 d . . .
O1 O 0.63436(15) 0.54637(12) 0.62840(6) 0.0326(2) Uani 1 1 d . . .
O2 O 0.78786(19) 0.11855(13) 0.61127(7) 0.0448(3) Uani 1 1 d . . .
O3 O 0.66930(17) 0.29622(13) 0.68881(6) 0.0374(3) Uani 1 1 d . . .
N1 N 0.87423(16) 0.39483(11) 0.40836(6) 0.0216(2) Uani 1 1 d . . .
N2 N 0.80141(16) 0.87703(11) 0.28218(6) 0.0233(2) Uani 1 1 d . . .
N3 N 0.64693(16) 0.91095(12) 0.13100(7) 0.0224(2) Uani 1 1 d . . .
C1 C 0.70734(18) 0.49881(15) 0.56046(8) 0.0242(3) Uani 1 1 d . . .
C2 C 0.76821(19) 0.35186(15) 0.54961(8) 0.0252(3) Uani 1 1 d . . .
C3 C 0.8498(2) 0.30691(15) 0.47499(8) 0.0249(3) Uani 1 1 d . . .
C4 C 0.7448(2) 0.24323(17) 0.61794(9) 0.0313(3) Uani 1 1 d . . .
C5 C 0.9644(2) 0.33869(14) 0.33111(8) 0.0238(3) Uani 1 1 d . . .
C6 C 0.9269(3) 0.20912(17) 0.31063(10) 0.0373(4) Uani 1 1 d . . .
C7 C 0.8347(2) 0.34993(18) 0.26798(9) 0.0333(3) Uani 1 1 d . . .
C8 C 0.73381(18) 0.59343(14) 0.48864(7) 0.0216(3) Uani 1 1 d . . .
C9 C 0.67801(19) 0.74029(15) 0.49306(8) 0.0245(3) Uani 1 1 d . . .
C10 C 0.70203(19) 0.82806(14) 0.42558(8) 0.0239(3) Uani 1 1 d . . .
C11 C 0.77943(18) 0.77970(14) 0.34823(7) 0.0208(2) Uani 1 1 d . . .
C12 C 0.84002(18) 0.63431(14) 0.34439(7) 0.0207(2) Uani 1 1 d . . .
C13 C 0.81720(17) 0.54104(13) 0.41357(7) 0.0196(2) Uani 1 1 d . . .
C14 C 0.6305(2) 0.99671(14) 0.26325(9) 0.0275(3) Uani 1 1 d . . .
C15 C 0.5160(2) 0.95874(15) 0.20609(8) 0.0255(3) Uani 1 1 d . . .
C16 C 0.9268(2) 0.82759(15) 0.20874(8) 0.0243(3) Uani 1 1 d . . .
C17 C 0.8170(2) 0.78793(14) 0.14987(8) 0.0240(3) Uani 1 1 d . . .
H3 H 0.896(2) 0.2093(18) 0.4670(10) 0.029(4) Uiso 1 1 d . . .
H5 H 1.094(2) 0.3484(16) 0.3146(10) 0.028(4) Uiso 1 1 d . . .
H9 H 0.629(3) 0.7780(18) 0.5455(11) 0.037(5) Uiso 1 1 d . . .
H12 H 0.897(2) 0.5963(17) 0.2937(10) 0.028(4) Uiso 1 1 d . . .
H61 H 0.840(3) 0.169(2) 0.3478(12) 0.045(5) Uiso 1 1 d . . .
H62 H 1.039(3) 0.142(2) 0.2814(12) 0.046(5) Uiso 1 1 d . . .
H71 H 0.697(3) 0.3936(19) 0.2825(11) 0.040(5) Uiso 1 1 d . . .
H72 H 0.884(3) 0.3724(18) 0.2133(11) 0.035(4) Uiso 1 1 d . . .
H14A H 0.678(3) 1.0746(19) 0.2380(10) 0.035(4) Uiso 1 1 d . . .
H14B H 0.542(2) 1.0248(17) 0.3128(11) 0.031(4) Uiso 1 1 d . . .
H15A H 0.465(2) 0.8818(18) 0.2304(10) 0.030(4) Uiso 1 1 d . . .
H15B H 0.412(2) 1.0427(18) 0.1905(10) 0.033(4) Uiso 1 1 d . . .
H16A H 1.037(2) 0.7486(17) 0.2226(9) 0.028(4) Uiso 1 1 d . . .
H16B H 0.980(2) 0.9064(17) 0.1827(10) 0.029(4) Uiso 1 1 d . . .
H17A H 0.900(2) 0.7654(17) 0.1007(10) 0.030(4) Uiso 1 1 d . . .
H17B H 0.762(2) 0.7097(16) 0.1741(9) 0.024(4) Uiso 1 1 d . . .
H30 H 0.635(3) 0.411(3) 0.6734(15) 0.076(7) Uiso 1 1 d . . .
H31 H 0.573(3) 0.8895(18) 0.0963(11) 0.038(5) Uiso 1 1 d . . .
H32 H 0.693(3) 0.9886(19) 0.1034(11) 0.037(5) Uiso 1 1 d . . .
O21 O 0.38558(15) 0.88330(10) 0.03991(6) 0.0300(2) Uani 1 1 d . . .
O22 O 0.23278(14) 0.86110(10) -0.05958(6) 0.0267(2) Uani 1 1 d . . .
O23 O 0.25905(15) 0.28075(10) 0.15427(6) 0.0283(2) Uani 1 1 d . . .
C21 C 0.30939(18) 0.81317(13) 0.00511(8) 0.0205(2) Uani 1 1 d . . .
C22 C 0.30371(17) 0.66950(12) 0.04251(7) 0.0183(2) Uani 1 1 d . . .
C23 C 0.35590(18) 0.62178(13) 0.12004(8) 0.0210(3) Uani 1 1 d . . .
C24 C 0.34079(19) 0.49176(14) 0.15695(8) 0.0229(3) Uani 1 1 d . . .
C25 C 0.27416(18) 0.40661(13) 0.11584(8) 0.0207(2) Uani 1 1 d . . .
C26 C 0.22566(18) 0.45185(13) 0.03767(8) 0.0214(3) Uani 1 1 d . . .
C27 C 0.24020(18) 0.58249(13) 0.00188(8) 0.0202(2) Uani 1 1 d . . .
H23 H 0.399(2) 0.6817(16) 0.1484(9) 0.025(4) Uiso 1 1 d . . .
H24 H 0.372(2) 0.4612(16) 0.2117(10) 0.026(4) Uiso 1 1 d . . .
H25 H 0.215(3) 0.237(2) 0.1220(13) 0.058(6) Uiso 1 1 d . . .
H26 H 0.185(2) 0.3912(16) 0.0087(9) 0.024(4) Uiso 1 1 d . . .
H27 H 0.207(2) 0.6114(16) -0.0534(10) 0.025(4) Uiso 1 1 d . . .
O10 O 0.14267(18) 0.14458(12) 0.05950(8) 0.0372(3) Uani 1 1 d . . .
H10 H 0.224(3) 0.057(2) 0.0514(13) 0.059(6) Uiso 1 1 d . . .
H11 H 0.024(4) 0.140(2) 0.0650(14) 0.066(7) 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 1.3552(15) . ?
O1 C1 1.2707(16) . ?
O2 C4 1.205(2) . ?
O3 C4 1.3378(19) . ?
O3 H30 1.10(2) . ?
N1 C3 1.3465(17) . ?
N1 C13 1.4026(17) . ?
N1 C5 1.4614(17) . ?
N2 C11 1.3925(16) . ?
N2 C16 1.4575(17) . ?
N2 C14 1.4755(17) . ?
N3 C17 1.4898(17) . ?
N3 C15 1.4911(18) . ?
N3 H31 0.937(19) . ?
N3 H32 0.966(18) . ?
C1 C2 1.427(2) . ?
C1 C8 1.4509(18) . ?
C2 C3 1.372(2) . ?
C2 C4 1.4921(18) . ?
C3 H3 0.951(17) . ?
C5 C6 1.493(2) . ?
C5 C7 1.497(2) . ?
C5 H5 0.956(17) . ?
C6 C7 1.497(2) . ?
C6 H61 0.95(2) . ?
C6 H62 0.99(2) . ?
C7 H71 0.958(18) . ?
C7 H72 0.952(18) . ?
C8 C13 1.4066(18) . ?
C8 C9 1.4070(19) . ?
C9 C10 1.3556(19) . ?
C9 H9 0.978(18) . ?
C10 C11 1.4197(18) . ?
C11 C12 1.3908(18) . ?
C12 C13 1.4063(17) . ?
C12 H12 0.961(16) . ?
C14 C15 1.516(2) . ?
C14 H14A 0.959(18) . ?
C14 H14B 0.982(17) . ?
C15 H15A 0.962(17) . ?
C15 H15B 0.979(17) . ?
C16 C17 1.5215(19) . ?
C16 H16A 0.966(16) . ?
C16 H16B 0.993(16) . ?
C17 H17A 0.951(17) . ?
C17 H17B 0.988(16) . ?
O21 C21 1.2583(15) . ?
O22 C21 1.2692(16) . ?
O23 C25 1.3565(15) . ?
O23 H25 0.89(2) . ?
C21 C22 1.4928(17) . ?
C22 C27 1.3916(17) . ?
C22 C23 1.3966(17) . ?
C23 C24 1.3854(18) . ?
C23 H23 0.961(16) . ?
C24 C25 1.3958(18) . ?
C24 H24 0.969(16) . ?
C25 C26 1.3954(18) . ?
C26 C27 1.3841(18) . ?
C26 H26 0.962(16) . ?
C27 H27 0.982(16) . ?
O10 H10 0.90(2) . ?
O10 H11 0.85(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H30 96.5(9) . . ?
C4 O3 H30 103.7(13) . . ?
C3 N1 C13 119.78(11) . . ?
C3 N1 C5 120.43(11) . . ?
C13 N1 C5 119.77(10) . . ?
C11 N2 C16 119.30(11) . . ?
C11 N2 C14 119.22(11) . . ?
C16 N2 C14 111.27(10) . . ?
C17 N3 C15 111.25(10) . . ?
C17 N3 H31 111.5(11) . . ?
C15 N3 H31 108.8(11) . . ?
C17 N3 H32 109.9(10) . . ?
C15 N3 H32 108.6(10) . . ?
H31 N3 H32 106.6(15) . . ?
O1 C1 C2 123.03(12) . . ?
O1 C1 C8 120.95(13) . . ?
C2 C1 C8 116.02(12) . . ?
C3 C2 C1 120.26(12) . . ?
C3 C2 C4 118.13(13) . . ?
C1 C2 C4 121.61(13) . . ?
N1 C3 C2 123.66(13) . . ?
N1 C3 H3 114.8(10) . . ?
C2 C3 H3 121.5(10) . . ?
O2 C4 O3 121.91(13) . . ?
O2 C4 C2 124.09(14) . . ?
O3 C4 C2 114.00(13) . . ?
N1 C5 C6 119.42(12) . . ?
N1 C5 C7 118.41(12) . . ?
C6 C5 C7 60.12(11) . . ?
N1 C5 H5 113.2(10) . . ?
C6 C5 H5 116.9(10) . . ?
C7 C5 H5 119.1(10) . . ?
C5 C6 C7 60.08(10) . . ?
C5 C6 H61 117.8(11) . . ?
C7 C6 H61 115.7(11) . . ?
C5 C6 H62 116.2(11) . . ?
C7 C6 H62 119.0(11) . . ?
H61 C6 H62 116.3(16) . . ?
C5 C7 C6 59.80(10) . . ?
C5 C7 H71 116.0(11) . . ?
C6 C7 H71 118.3(11) . . ?
C5 C7 H72 117.4(11) . . ?
C6 C7 H72 119.5(10) . . ?
H71 C7 H72 114.7(15) . . ?
C13 C8 C9 118.56(11) . . ?
C13 C8 C1 121.10(12) . . ?
C9 C8 C1 120.34(12) . . ?
C10 C9 C8 119.98(12) . . ?
C10 C9 H9 120.3(10) . . ?
C8 C9 H9 119.6(10) . . ?
F1 C10 C9 118.78(12) . . ?
F1 C10 C11 117.98(11) . . ?
C9 C10 C11 123.17(12) . . ?
C12 C11 N2 123.67(11) . . ?
C12 C11 C10 116.77(11) . . ?
N2 C11 C10 119.45(12) . . ?
C11 C12 C13 121.09(12) . . ?
C11 C12 H12 119.9(9) . . ?
C13 C12 H12 119.0(9) . . ?
N1 C13 C12 120.46(11) . . ?
N1 C13 C8 119.16(11) . . ?
C12 C13 C8 120.37(12) . . ?
N2 C14 C15 111.09(11) . . ?
N2 C14 H14A 108.3(10) . . ?
C15 C14 H14A 109.0(10) . . ?
N2 C14 H14B 110.7(10) . . ?
C15 C14 H14B 108.5(10) . . ?
H14A C14 H14B 109.2(14) . . ?
N3 C15 C14 110.28(11) . . ?
N3 C15 H15A 106.9(10) . . ?
C14 C15 H15A 110.8(10) . . ?
N3 C15 H15B 107.7(10) . . ?
C14 C15 H15B 109.1(10) . . ?
H15A C15 H15B 112.0(14) . . ?
N2 C16 C17 113.03(11) . . ?
N2 C16 H16A 109.7(9) . . ?
C17 C16 H16A 110.4(9) . . ?
N2 C16 H16B 106.5(9) . . ?
C17 C16 H16B 109.3(9) . . ?
H16A C16 H16B 107.7(13) . . ?
N3 C17 C16 108.97(11) . . ?
N3 C17 H17A 108.1(10) . . ?
C16 C17 H17A 110.4(10) . . ?
N3 C17 H17B 106.5(9) . . ?
C16 C17 H17B 111.3(9) . . ?
H17A C17 H17B 111.4(13) . . ?
C25 O23 H25 109.5(14) . . ?
O21 C21 O22 122.59(11) . . ?
O21 C21 C22 118.80(11) . . ?
O22 C21 C22 118.59(11) . . ?
C27 C22 C23 118.77(11) . . ?
C27 C22 C21 120.63(11) . . ?
C23 C22 C21 120.57(11) . . ?
C24 C23 C22 120.94(12) . . ?
C24 C23 H23 120.0(9) . . ?
C22 C23 H23 119.0(9) . . ?
C23 C24 C25 119.58(12) . . ?
C23 C24 H24 120.5(9) . . ?
C25 C24 H24 119.9(9) . . ?
O23 C25 C26 122.10(11) . . ?
O23 C25 C24 117.91(12) . . ?
C26 C25 C24 119.98(11) . . ?
C27 C26 C25 119.71(12) . . ?
C27 C26 H26 120.5(9) . . ?
C25 C26 H26 119.7(9) . . ?
C26 C27 C22 121.00(12) . . ?
C26 C27 H27 118.2(9) . . ?
C22 C27 H27 120.8(9) . . ?
H10 O10 H11 108(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
O1 C1 C2 C3 -178.62(12) . . . . ?
C8 C1 C2 C3 1.23(18) . . . . ?
O1 C1 C2 C4 1.7(2) . . . . ?
C8 C1 C2 C4 -178.46(11) . . . . ?
C13 N1 C3 C2 0.94(19) . . . . ?
C5 N1 C3 C2 179.34(12) . . . . ?
C1 C2 C3 N1 -1.4(2) . . . . ?
C4 C2 C3 N1 178.34(12) . . . . ?
C3 C2 C4 O2 -2.2(2) . . . . ?
C1 C2 C4 O2 177.48(14) . . . . ?
C3 C2 C4 O3 178.16(12) . . . . ?
C1 C2 C4 O3 -2.14(18) . . . . ?
C3 N1 C5 C6 35.10(18) . . . . ?
C13 N1 C5 C6 -146.50(13) . . . . ?
C3 N1 C5 C7 104.90(15) . . . . ?
C13 N1 C5 C7 -76.70(16) . . . . ?
N1 C5 C6 C7 107.82(14) . . . . ?
N1 C5 C7 C6 -109.46(14) . . . . ?
O1 C1 C8 C13 179.06(12) . . . . ?
C2 C1 C8 C13 -0.79(18) . . . . ?
O1 C1 C8 C9 -0.26(19) . . . . ?
C2 C1 C8 C9 179.89(11) . . . . ?
C13 C8 C9 C10 1.10(19) . . . . ?
C1 C8 C9 C10 -179.57(12) . . . . ?
C8 C9 C10 F1 -175.88(11) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C16 N2 C11 C12 -12.43(18) . . . . ?
C14 N2 C11 C12 129.81(13) . . . . ?
C16 N2 C11 C10 163.66(11) . . . . ?
C14 N2 C11 C10 -54.11(17) . . . . ?
F1 C10 C11 C12 174.06(11) . . . . ?
C9 C10 C11 C12 -2.89(19) . . . . ?
F1 C10 C11 N2 -2.29(18) . . . . ?
C9 C10 C11 N2 -179.24(12) . . . . ?
N2 C11 C12 C13 178.80(11) . . . . ?
C10 C11 C12 C13 2.62(18) . . . . ?
C3 N1 C13 C12 -179.40(11) . . . . ?
C5 N1 C13 C12 2.19(17) . . . . ?
C3 N1 C13 C8 -0.45(17) . . . . ?
C5 N1 C13 C8 -178.86(11) . . . . ?
C11 C12 C13 N1 178.32(11) . . . . ?
C11 C12 C13 C8 -0.62(18) . . . . ?
C9 C8 C13 N1 179.74(11) . . . . ?
C1 C8 C13 N1 0.42(18) . . . . ?
C9 C8 C13 C12 -1.30(18) . . . . ?
C1 C8 C13 C12 179.37(11) . . . . ?
C11 N2 C14 C15 -89.84(14) . . . . ?
C16 N2 C14 C15 55.19(15) . . . . ?
C17 N3 C15 C14 57.66(14) . . . . ?
N2 C14 C15 N3 -56.27(15) . . . . ?
C11 N2 C16 C17 89.42(14) . . . . ?
C14 N2 C16 C17 -55.59(15) . . . . ?
C15 N3 C17 C16 -56.22(14) . . . . ?
N2 C16 C17 N3 55.60(14) . . . . ?
O21 C21 C22 C27 -173.09(12) . . . . ?
O22 C21 C22 C27 8.60(18) . . . . ?
O21 C21 C22 C23 9.03(18) . . . . ?
O22 C21 C22 C23 -169.28(11) . . . . ?
C27 C22 C23 C24 -1.49(18) . . . . ?
C21 C22 C23 C24 176.44(11) . . . . ?
C22 C23 C24 C25 0.59(19) . . . . ?
C23 C24 C25 O23 -179.23(11) . . . . ?
C23 C24 C25 C26 0.82(19) . . . . ?
O23 C25 C26 C27 178.75(11) . . . . ?
C24 C25 C26 C27 -1.29(19) . . . . ?
C25 C26 C27 C22 0.38(19) . . . . ?
C23 C22 C27 C26 1.00(18) . . . . ?
C21 C22 C27 C26 -176.92(11) . . . . ?

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
O3 H30 O1 1.10(2) 1.45(3) 2.5149(16) 160(2) .
N3 H31 O21 0.937(19) 1.789(19) 2.7086(15) 166.2(16) .
N3 H32 O22 0.966(18) 1.767(19) 2.7300(15) 175.2(16) 2_675
O23 H25 O10 0.89(2) 1.72(2) 2.6110(16) 177(2) .
O10 H10 O21 0.90(2) 1.79(2) 2.6957(16) 178(2) 1_545
O10 H11 O22 0.85(2) 1.87(3) 2.7198(16) 171(2) 2_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1993398'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-03-29 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 F N3 O3, C7 H5 O5, 2.167(H2 O)'
_chemical_formula_sum            'C24 H28.33 F N3 O10.17'
_chemical_formula_weight         540.47

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.1210(7)
_cell_length_b                   27.264(2)
_cell_length_c                   10.3393(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.365(1)
_cell_angle_gamma                90.00
_cell_volume                     2566.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7185
_cell_measurement_theta_min      2.475
_cell_measurement_theta_max      30.490

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1134.7
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            28802
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         29.00
_reflns_number_total             6829
_reflns_number_gt                5346
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.9557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         6829
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.03121(9) 0.50616(3) 0.16772(8) 0.02329(19) Uani 1 1 d . . .
O1 O 0.35861(11) 0.51033(4) 0.57816(9) 0.0210(2) Uani 1 1 d . . .
O2 O 0.38609(12) 0.42740(5) 0.90790(10) 0.0300(3) Uani 1 1 d . . .
O3 O 0.47381(11) 0.48978(4) 0.79863(10) 0.0250(2) Uani 1 1 d . . .
N1 N 0.06938(12) 0.39684(4) 0.61665(10) 0.0171(2) Uani 1 1 d . . .
N2 N -0.16104(12) 0.42699(4) 0.18749(10) 0.0159(2) Uani 1 1 d . . .
N3 N -0.34234(13) 0.38082(4) -0.01250(11) 0.0170(2) Uani 1 1 d . . .
C1 C 0.26935(14) 0.47544(5) 0.58777(12) 0.0145(2) Uani 1 1 d . . .
C2 C 0.27103(14) 0.44538(5) 0.70148(12) 0.0167(3) Uani 1 1 d . . .
C3 C 0.17135(15) 0.40828(5) 0.71064(13) 0.0185(3) Uani 1 1 d . . .
C4 C 0.38054(15) 0.45345(5) 0.81098(13) 0.0201(3) Uani 1 1 d . . .
C5 C -0.04121(16) 0.35954(6) 0.63977(14) 0.0231(3) Uani 1 1 d . . .
C6 C 0.0068(2) 0.31323(7) 0.70715(19) 0.0394(4) Uani 1 1 d . . .
C7 C -0.0416(2) 0.31223(6) 0.56624(18) 0.0322(4) Uani 1 1 d . . .
C8 C 0.15934(13) 0.46302(5) 0.48623(12) 0.0136(2) Uani 1 1 d . . .
C9 C 0.14816(14) 0.49009(5) 0.36992(12) 0.0154(3) Uani 1 1 d . . .
C10 C 0.04388(14) 0.47771(5) 0.27593(12) 0.0151(3) Uani 1 1 d . . .
C11 C -0.05374(13) 0.43772(5) 0.28624(12) 0.0142(2) Uani 1 1 d . . .
C12 C -0.04306(14) 0.41172(5) 0.40187(12) 0.0152(3) Uani 1 1 d . . .
C13 C 0.06172(14) 0.42402(5) 0.50112(12) 0.0140(2) Uani 1 1 d . . .
C14 C -0.10984(15) 0.42049(5) 0.05549(12) 0.0175(3) Uani 1 1 d . . .
C15 C -0.23905(16) 0.42091(5) -0.04347(13) 0.0191(3) Uani 1 1 d . . .
C16 C -0.26516(14) 0.38834(5) 0.21892(13) 0.0168(3) Uani 1 1 d . . .
C17 C -0.39468(15) 0.38786(5) 0.11993(13) 0.0180(3) Uani 1 1 d . . .
H3 H 0.1710(18) 0.3878(6) 0.7864(16) 0.021(4) Uiso 1 1 d . . .
H5 H -0.135(2) 0.3726(6) 0.6593(17) 0.027(4) Uiso 1 1 d . . .
H9 H 0.2128(18) 0.5180(6) 0.3587(16) 0.021(4) Uiso 1 1 d . . .
H10 H -0.1050(18) 0.3849(6) 0.4158(16) 0.022(4) Uiso 1 1 d . . .
H30 H 0.456(3) 0.5026(8) 0.714(2) 0.055(7) Uiso 1 1 d . . .
H31 H -0.292(2) 0.3504(7) -0.0148(18) 0.036(5) Uiso 1 1 d . . .
H32 H -0.4181(19) 0.3808(6) -0.0702(17) 0.023(4) Uiso 1 1 d . . .
H61 H -0.055(3) 0.3013(8) 0.769(2) 0.055(7) Uiso 1 1 d . . .
H62 H 0.108(2) 0.3091(8) 0.724(2) 0.043(6) Uiso 1 1 d . . .
H71 H -0.137(2) 0.2989(7) 0.543(2) 0.045(6) Uiso 1 1 d . . .
H72 H 0.035(2) 0.3086(7) 0.5033(19) 0.036(5) Uiso 1 1 d . . .
H141 H -0.0554(18) 0.3891(6) 0.0495(16) 0.024(4) Uiso 1 1 d . . .
H142 H -0.0419(19) 0.4456(6) 0.0344(16) 0.023(4) Uiso 1 1 d . . .
H151 H -0.2070(19) 0.4154(6) -0.1272(18) 0.026(4) Uiso 1 1 d . . .
H152 H -0.2964(18) 0.4513(6) -0.0441(16) 0.021(4) Uiso 1 1 d . . .
H161 H -0.3057(17) 0.3966(6) 0.3039(16) 0.018(4) Uiso 1 1 d . . .
H162 H -0.2159(18) 0.3558(6) 0.2231(16) 0.023(4) Uiso 1 1 d . . .
H171 H -0.4608(19) 0.3611(6) 0.1374(16) 0.023(4) Uiso 1 1 d . . .
H172 H -0.4466(17) 0.4185(6) 0.1202(15) 0.014(4) Uiso 1 1 d . . .
O21 O 0.69474(12) 0.79435(4) 0.49850(10) 0.0234(2) Uani 1 1 d . . .
O22 O 0.82316(12) 0.75374(4) 0.65502(10) 0.0260(2) Uani 1 1 d . . .
O24 O 0.39938(12) 0.66151(4) 0.25640(10) 0.0250(2) Uani 1 1 d . . .
O25 O 0.40448(11) 0.58521(4) 0.41610(10) 0.0212(2) Uani 1 1 d . . .
O26 O 0.57598(11) 0.58575(3) 0.64442(9) 0.0174(2) Uani 1 1 d . . .
C21 C 0.72941(15) 0.75550(5) 0.55981(13) 0.0178(3) Uani 1 1 d . . .
C22 C 0.65139(14) 0.70905(5) 0.51894(12) 0.0165(3) Uani 1 1 d . . .
C23 C 0.56830(15) 0.70674(5) 0.40093(13) 0.0176(3) Uani 1 1 d . . .
H23 H 0.5722(18) 0.7340(6) 0.3424(16) 0.023(4) Uiso 1 1 d . . .
C24 C 0.48565(15) 0.66527(5) 0.36876(12) 0.0168(3) Uani 1 1 d . . .
C25 C 0.48802(14) 0.62489(5) 0.45232(12) 0.0152(3) Uani 1 1 d . . .
C26 C 0.57604(14) 0.62658(5) 0.56772(12) 0.0143(2) Uani 1 1 d . . .
C27 C 0.65627(15) 0.66859(5) 0.60108(13) 0.0164(3) Uani 1 1 d . . .
H27 H 0.7121(17) 0.6695(6) 0.6794(16) 0.016(4) Uiso 1 1 d . . .
H24 H 0.379(2) 0.6920(9) 0.224(2) 0.052(6) Uiso 1 1 d . . .
H25 H 0.410(2) 0.5630(8) 0.478(2) 0.043(6) Uiso 1 1 d . . .
H26 H 0.637(2) 0.5905(7) 0.711(2) 0.040(5) Uiso 1 1 d . . .
O10 O 0.75470(12) 0.59745(5) 0.86232(11) 0.0251(2) Uani 1 1 d . . .
H1 H 0.719(2) 0.5909(8) 0.935(2) 0.050(6) Uiso 1 1 d . . .
H2 H 0.802(2) 0.6243(9) 0.871(2) 0.048(6) Uiso 1 1 d . . .
O11 O 0.8808(19) 0.6914(6) 0.8911(15) 0.046(2) Uani 0.42(4) 1 d P . .
O12 O 0.9258(17) 0.6817(3) 0.8485(18) 0.048(3) Uani 0.58(4) 1 d P . .
H11 H 0.885(3) 0.7057(11) 0.799(3) 0.091(10) Uiso 1 1 d . . .
H12 H 0.989(3) 0.6938(10) 0.906(3) 0.072(8) Uiso 1 1 d . . .
O13 O 0.3829(9) 0.3104(3) 0.9452(8) 0.046(3) Uani 0.167(4) 1 d P . .
H13 H 0.3840 0.3414 0.9352 0.069 Uiso 0.167(4) 1 d PR . .
H14 H 0.3087 0.3098 0.9913 0.069 Uiso 0.167(4) 1 d PR . .


_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 1.3607(14) . ?
O1 C1 1.2597(16) . ?
O2 C4 1.2269(17) . ?
O3 C4 1.3168(18) . ?
O3 H30 0.94(2) . ?
N1 C3 1.3418(16) . ?
N1 C13 1.4040(16) . ?
N1 C5 1.4620(18) . ?
N2 C11 1.4031(15) . ?
N2 C16 1.4676(17) . ?
N2 C14 1.4789(17) . ?
N3 C17 1.4888(17) . ?
N3 C15 1.4901(18) . ?
N3 H31 0.95(2) . ?
N3 H32 0.886(17) . ?
C1 C2 1.4325(18) . ?
C1 C8 1.4492(16) . ?
C2 C3 1.3670(19) . ?
C2 C4 1.4816(17) . ?
C3 H3 0.962(17) . ?
C5 C6 1.495(2) . ?
C5 C7 1.497(2) . ?
C5 H5 0.961(18) . ?
C6 C7 1.498(3) . ?
C6 H61 0.93(2) . ?
C6 H62 0.93(2) . ?
C7 H71 0.96(2) . ?
C7 H72 0.99(2) . ?
C8 C13 1.4011(18) . ?
C8 C9 1.4095(18) . ?
C9 C10 1.3618(17) . ?
C9 H9 0.973(17) . ?
C10 C11 1.4156(18) . ?
C11 C12 1.3883(18) . ?
C12 C13 1.4014(17) . ?
C12 H10 0.940(17) . ?
C14 C15 1.5147(18) . ?
C14 H141 0.992(17) . ?
C14 H142 0.958(18) . ?
C15 H151 0.941(18) . ?
C15 H152 0.980(17) . ?
C16 C17 1.5169(17) . ?
C16 H161 0.999(16) . ?
C16 H162 0.995(17) . ?
C17 H171 0.970(17) . ?
C17 H172 0.960(16) . ?
O21 C21 1.2650(16) . ?
O22 C21 1.2664(16) . ?
O24 C24 1.3682(15) . ?
O24 H24 0.91(2) . ?
O25 C25 1.3631(15) . ?
O25 H25 0.88(2) . ?
O26 C26 1.3667(15) . ?
O26 H26 0.87(2) . ?
C21 C22 1.5011(18) . ?
C22 C27 1.3914(19) . ?
C22 C23 1.3995(17) . ?
C23 C24 1.3885(18) . ?
C23 H23 0.961(17) . ?
C24 C25 1.3989(19) . ?
C25 C26 1.3992(17) . ?
C26 C27 1.3916(18) . ?
C27 H27 0.931(16) . ?
O10 H1 0.85(2) . ?
O10 H2 0.85(2) . ?
O11 H11 1.03(3) . ?
O11 H12 0.99(3) . ?
O12 H11 0.90(3) . ?
O12 H12 0.87(3) . ?
O13 H13 0.8501 . ?
O13 H14 0.8500 . ?

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
C4 O3 H30 106.7(14) . . ?
C3 N1 C13 119.43(11) . . ?
C3 N1 C5 119.92(11) . . ?
C13 N1 C5 120.40(11) . . ?
C11 N2 C16 114.93(10) . . ?
C11 N2 C14 116.87(11) . . ?
C16 N2 C14 111.21(10) . . ?
C17 N3 C15 110.12(10) . . ?
C17 N3 H31 108.6(12) . . ?
C15 N3 H31 108.6(12) . . ?
C17 N3 H32 109.9(11) . . ?
C15 N3 H32 109.5(11) . . ?
H31 N3 H32 110.1(16) . . ?
O1 C1 C2 121.39(11) . . ?
O1 C1 C8 122.85(12) . . ?
C2 C1 C8 115.75(11) . . ?
C3 C2 C1 120.34(11) . . ?
C3 C2 C4 118.57(12) . . ?
C1 C2 C4 121.09(12) . . ?
N1 C3 C2 123.87(12) . . ?
N1 C3 H3 114.8(10) . . ?
C2 C3 H3 121.4(10) . . ?
O2 C4 O3 121.25(12) . . ?
O2 C4 C2 122.13(13) . . ?
O3 C4 C2 116.62(12) . . ?
N1 C5 C6 118.53(13) . . ?
N1 C5 C7 119.83(14) . . ?
C6 C5 C7 60.07(12) . . ?
N1 C5 H5 114.1(11) . . ?
C6 C5 H5 117.1(11) . . ?
C7 C5 H5 116.8(11) . . ?
C5 C6 C7 60.03(11) . . ?
C5 C6 H61 116.3(14) . . ?
C7 C6 H61 120.4(14) . . ?
C5 C6 H62 116.5(13) . . ?
C7 C6 H62 114.0(13) . . ?
H61 C6 H62 117.3(19) . . ?
C5 C7 C6 59.90(12) . . ?
C5 C7 H71 115.3(12) . . ?
C6 C7 H71 117.2(13) . . ?
C5 C7 H72 116.2(11) . . ?
C6 C7 H72 117.7(11) . . ?
H71 C7 H72 117.6(17) . . ?
C13 C8 C9 118.45(11) . . ?
C13 C8 C1 121.01(11) . . ?
C9 C8 C1 120.54(12) . . ?
C10 C9 C8 119.45(12) . . ?
C10 C9 H9 120.7(10) . . ?
C8 C9 H9 119.8(10) . . ?
F1 C10 C9 117.88(11) . . ?
F1 C10 C11 118.52(11) . . ?
C9 C10 C11 123.58(12) . . ?
C12 C11 N2 122.06(12) . . ?
C12 C11 C10 116.46(11) . . ?
N2 C11 C10 121.38(11) . . ?
C11 C12 C13 121.24(12) . . ?
C11 C12 H10 121.1(10) . . ?
C13 C12 H10 117.7(10) . . ?
C8 C13 C12 120.77(11) . . ?
C8 C13 N1 119.59(11) . . ?
C12 C13 N1 119.63(12) . . ?
N2 C14 C15 110.31(11) . . ?
N2 C14 H141 110.3(10) . . ?
C15 C14 H141 109.7(10) . . ?
N2 C14 H142 111.6(10) . . ?
C15 C14 H142 109.2(10) . . ?
H141 C14 H142 105.6(14) . . ?
N3 C15 C14 109.02(11) . . ?
N3 C15 H151 108.4(11) . . ?
C14 C15 H151 110.4(11) . . ?
N3 C15 H152 106.2(10) . . ?
C14 C15 H152 113.8(10) . . ?
H151 C15 H152 108.8(14) . . ?
N2 C16 C17 110.20(11) . . ?
N2 C16 H161 108.1(9) . . ?
C17 C16 H161 106.3(9) . . ?
N2 C16 H162 110.8(10) . . ?
C17 C16 H162 110.7(9) . . ?
H161 C16 H162 110.6(13) . . ?
N3 C17 C16 110.04(11) . . ?
N3 C17 H171 108.1(10) . . ?
C16 C17 H171 110.4(10) . . ?
N3 C17 H172 107.4(9) . . ?
C16 C17 H172 110.8(9) . . ?
H171 C17 H172 110.0(13) . . ?
C24 O24 H24 109.5(14) . . ?
C25 O25 H25 110.0(14) . . ?
C26 O26 H26 108.3(13) . . ?
O21 C21 O22 123.96(12) . . ?
O21 C21 C22 117.70(11) . . ?
O22 C21 C22 118.31(12) . . ?
C27 C22 C23 119.52(12) . . ?
C27 C22 C21 119.97(11) . . ?
C23 C22 C21 120.46(12) . . ?
C24 C23 C22 120.27(12) . . ?
C24 C23 H23 121.3(10) . . ?
C22 C23 H23 118.4(10) . . ?
O24 C24 C23 122.78(12) . . ?
O24 C24 C25 116.92(11) . . ?
C23 C24 C25 120.29(11) . . ?
O25 C25 C24 117.83(11) . . ?
O25 C25 C26 122.95(12) . . ?
C24 C25 C26 119.21(12) . . ?
O26 C26 C27 123.00(11) . . ?
O26 C26 C25 116.63(11) . . ?
C27 C26 C25 120.37(12) . . ?
C22 C27 C26 120.25(12) . . ?
C22 C27 H27 120.3(10) . . ?
C26 C27 H27 119.4(10) . . ?
H1 O10 H2 107(2) . . ?
H11 O11 H12 91(3) . . ?
H11 O12 H12 110(3) . . ?
H13 O13 H14 95.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.83(13) . . . . ?
C8 C1 C2 C3 -1.19(18) . . . . ?
O1 C1 C2 C4 -1.5(2) . . . . ?
C8 C1 C2 C4 178.45(12) . . . . ?
C13 N1 C3 C2 -0.2(2) . . . . ?
C5 N1 C3 C2 -174.36(13) . . . . ?
C1 C2 C3 N1 1.2(2) . . . . ?
C4 C2 C3 N1 -178.46(13) . . . . ?
C3 C2 C4 O2 1.4(2) . . . . ?
C1 C2 C4 O2 -178.24(13) . . . . ?
C3 C2 C4 O3 -179.51(12) . . . . ?
C1 C2 C4 O3 0.84(19) . . . . ?
C3 N1 C5 C6 -43.6(2) . . . . ?
C13 N1 C5 C6 142.24(15) . . . . ?
C3 N1 C5 C7 -113.57(16) . . . . ?
C13 N1 C5 C7 72.29(18) . . . . ?
N1 C5 C6 C7 -109.89(16) . . . . ?
N1 C5 C7 C6 107.77(16) . . . . ?
O1 C1 C8 C13 -179.73(12) . . . . ?
C2 C1 C8 C13 0.28(18) . . . . ?
O1 C1 C8 C9 0.2(2) . . . . ?
C2 C1 C8 C9 -179.78(12) . . . . ?
C13 C8 C9 C10 -0.06(19) . . . . ?
C1 C8 C9 C10 -179.99(12) . . . . ?
C8 C9 C10 F1 176.69(12) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C16 N2 C11 C12 3.30(18) . . . . ?
C14 N2 C11 C12 -129.77(14) . . . . ?
C16 N2 C11 C10 -172.86(12) . . . . ?
C14 N2 C11 C10 54.08(17) . . . . ?
F1 C10 C11 C12 -175.91(12) . . . . ?
C9 C10 C11 C12 2.5(2) . . . . ?
F1 C10 C11 N2 0.45(19) . . . . ?
C9 C10 C11 N2 178.90(12) . . . . ?
N2 C11 C12 C13 -177.85(12) . . . . ?
C10 C11 C12 C13 -1.52(19) . . . . ?
C9 C8 C13 C12 1.00(19) . . . . ?
C1 C8 C13 C12 -179.07(12) . . . . ?
C9 C8 C13 N1 -179.25(12) . . . . ?
C1 C8 C13 N1 0.68(19) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C11 C12 C13 N1 -179.91(12) . . . . ?
C3 N1 C13 C8 -0.77(19) . . . . ?
C5 N1 C13 C8 173.39(12) . . . . ?
C3 N1 C13 C12 178.98(12) . . . . ?
C5 N1 C13 C12 -6.86(19) . . . . ?
C11 N2 C14 C15 -166.92(11) . . . . ?
C16 N2 C14 C15 58.37(14) . . . . ?
C17 N3 C15 C14 59.27(14) . . . . ?
N2 C14 C15 N3 -58.64(15) . . . . ?
C11 N2 C16 C17 167.08(11) . . . . ?
C14 N2 C16 C17 -57.27(14) . . . . ?
C15 N3 C17 C16 -58.84(14) . . . . ?
N2 C16 C17 N3 57.32(15) . . . . ?
O21 C21 C22 C27 -163.56(13) . . . . ?
O22 C21 C22 C27 14.8(2) . . . . ?
O21 C21 C22 C23 13.7(2) . . . . ?
O22 C21 C22 C23 -167.90(13) . . . . ?
C27 C22 C23 C24 3.1(2) . . . . ?
C21 C22 C23 C24 -174.18(13) . . . . ?
C22 C23 C24 O24 178.21(13) . . . . ?
C22 C23 C24 C25 -1.8(2) . . . . ?
O24 C24 C25 O25 -0.23(19) . . . . ?
C23 C24 C25 O25 179.82(13) . . . . ?
O24 C24 C25 C26 179.14(12) . . . . ?
C23 C24 C25 C26 -0.8(2) . . . . ?
O25 C25 C26 O26 0.46(19) . . . . ?
C24 C25 C26 O26 -178.87(12) . . . . ?
O25 C25 C26 C27 -178.44(13) . . . . ?
C24 C25 C26 C27 2.22(19) . . . . ?
C23 C22 C27 C26 -1.7(2) . . . . ?
C21 C22 C27 C26 175.60(12) . . . . ?
O26 C26 C27 C22 -179.80(12) . . . . ?
C25 C26 C27 C22 -1.0(2) . . . . ?

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
O3 H30 O1 0.94(2) 1.63(2) 2.5165(14) 154(2) .
N3 H31 O21 0.95(2) 1.77(2) 2.7145(15) 173.1(18) 2_545
N3 H32 O2 0.886(17) 2.193(17) 2.8612(16) 131.9(14) 1_454
N3 H32 O24 0.886(17) 2.260(17) 2.7942(15) 118.6(14) 3_565
O24 H24 O22 0.91(2) 1.71(2) 2.6144(14) 173(2) 4_575
O25 H25 O1 0.88(2) 1.85(2) 2.6895(14) 160(2) .
O26 H26 O10 0.87(2) 1.86(2) 2.7210(14) 174(2) .
O10 H1 O2 0.85(2) 2.00(2) 2.8480(16) 173(2) 3_667
O10 H2 O11 0.85(2) 1.97(3) 2.816(10) 171(2) .
O10 H2 O12 0.85(2) 1.95(3) 2.785(6) 165(2) .
O11 H11 O22 1.03(3) 2.04(3) 2.996(7) 153(3) .
O12 H11 O22 0.90(3) 2.04(3) 2.919(5) 167(3) .
O11 H12 O21 0.99(3) 2.08(3) 3.035(11) 161(3) 4_676
O12 H12 O21 0.87(3) 2.08(3) 2.899(4) 157(3) 4_676
O13 H13 O2 0.85 2.36 3.213(8) 179.7 .
O13 H14 O11 0.85 2.17 3.02(2) 179.7 3_667

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049
