# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1567143'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2018-01-19 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, C4 H3 O4, 0.155(H2 O)'
_chemical_formula_sum            'C21 H22.31 F N3 O7.16'
_chemical_formula_weight         450.21

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                   8.0133(9)
_cell_length_b                   37.244(4)
_cell_length_c                   6.9698(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.806(2)
_cell_angle_gamma                90.00
_cell_volume                     2077.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5843
_cell_measurement_theta_min      2.545
_cell_measurement_theta_max      30.435

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             942
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_T_max  0.9886
_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_%        ?
_diffrn_reflns_number            22847
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         29.00
_reflns_number_total             5508
_reflns_number_gt                4468
_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)+(0.0586P)²+0.6321P] 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         5508
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 -0.03785(9) 0.55156(2) 0.55890(12) 0.02618(19) Uani 1 1 d . . .
N1 N 0.62733(13) 0.55556(3) 0.79776(15) 0.0194(2) Uani 1 1 d . . .
N2 N 0.11155(14) 0.61765(3) 0.59520(16) 0.0204(2) Uani 1 1 d . . .
N3 N -0.01278(14) 0.68526(3) 0.45483(17) 0.0196(2) Uani 1 1 d . . .
O1 O 0.39708(13) 0.45774(2) 0.71936(15) 0.0290(2) Uani 1 1 d . . .
O2 O 0.89787(14) 0.46119(3) 0.87928(17) 0.0382(3) Uani 1 1 d . . .
O3 O 0.67246(15) 0.42780(3) 0.81172(16) 0.0330(3) Uani 1 1 d . . .
C1 C 0.46843(17) 0.48773(3) 0.74354(18) 0.0206(3) Uani 1 1 d . . .
C2 C 0.64107(17) 0.49136(3) 0.80349(18) 0.0210(3) Uani 1 1 d . . .
C3 C 0.71203(17) 0.52465(4) 0.82869(18) 0.0213(3) Uani 1 1 d . . .
C4 C 0.75068(19) 0.45933(4) 0.83648(19) 0.0268(3) Uani 1 1 d . . .
C5 C 0.71659(16) 0.58946(4) 0.8092(2) 0.0223(3) Uani 1 1 d . . .
C6 C 0.83495(19) 0.59582(4) 0.9781(2) 0.0314(3) Uani 1 1 d . . .
C7 C 0.67507(18) 0.61685(4) 0.9578(2) 0.0279(3) Uani 1 1 d . . .
C8 C 0.37823(16) 0.52134(3) 0.70995(17) 0.0183(2) Uani 1 1 d . . .
C9 C 0.20794(16) 0.52077(3) 0.65052(19) 0.0206(3) Uani 1 1 d . . .
C10 C 0.12732(15) 0.55234(3) 0.61319(18) 0.0195(2) Uani 1 1 d . . .
C11 C 0.20587(16) 0.58623(3) 0.63130(17) 0.0184(2) Uani 1 1 d . . .
C12 C 0.37287(16) 0.58677(3) 0.69249(18) 0.0189(2) Uani 1 1 d . . .
C13 C 0.45928(15) 0.55461(3) 0.73380(17) 0.0176(2) Uani 1 1 d . . .
C14 C 0.04326(17) 0.62149(3) 0.39513(19) 0.0225(3) Uani 1 1 d . . .
C15 C -0.08719(17) 0.65084(3) 0.3823(2) 0.0231(3) Uani 1 1 d . . .
C16 C 0.18856(19) 0.65126(4) 0.6629(2) 0.0262(3) Uani 1 1 d . . .
C17 C 0.05912(19) 0.68100(4) 0.6545(2) 0.0261(3) Uani 1 1 d . . .
H1 H 0.067(2) 0.6913(4) 0.373(2) 0.026(4) Uiso 1 1 d . . .
H2 H -0.090(2) 0.7021(5) 0.457(2) 0.033(5) Uiso 1 1 d . . .
H3 H 0.828(2) 0.5272(4) 0.871(2) 0.017(4) Uiso 1 1 d . . .
H4 H 0.558(3) 0.4341(7) 0.772(4) 0.074(8) Uiso 1 1 d . . .
H5 H 0.746(2) 0.5976(4) 0.687(2) 0.028(4) Uiso 1 1 d . . .
H9 H 0.149(2) 0.4981(5) 0.641(2) 0.027(4) Uiso 1 1 d . . .
H12 H 0.4290(19) 0.6092(4) 0.704(2) 0.020(4) Uiso 1 1 d . . .
H61 H 0.842(2) 0.5768(6) 1.071(3) 0.044(5) Uiso 1 1 d . . .
H62 H 0.935(2) 0.6079(5) 0.955(3) 0.037(5) Uiso 1 1 d . . .
H71 H 0.588(2) 0.6110(5) 1.043(2) 0.028(4) Uiso 1 1 d . . .
H72 H 0.680(2) 0.6419(5) 0.918(3) 0.034(5) Uiso 1 1 d . . .
H141 H 0.138(2) 0.6274(5) 0.312(3) 0.033(4) Uiso 1 1 d . . .
H142 H -0.009(2) 0.5987(5) 0.351(2) 0.028(4) Uiso 1 1 d . . .
H151 H -0.130(2) 0.6540(4) 0.251(2) 0.026(4) Uiso 1 1 d . . .
H152 H -0.179(2) 0.6454(5) 0.461(3) 0.033(4) Uiso 1 1 d . . .
H161 H 0.286(2) 0.6591(5) 0.584(3) 0.034(5) Uiso 1 1 d . . .
H162 H 0.228(2) 0.6486(5) 0.797(3) 0.033(4) Uiso 1 1 d . . .
H171 H 0.110(2) 0.7040(5) 0.692(2) 0.032(4) Uiso 1 1 d . . .
H172 H -0.033(2) 0.6756(5) 0.739(3) 0.031(4) Uiso 1 1 d . . .
O21 O 0.83809(11) 0.71341(3) 0.06109(15) 0.0258(2) Uani 1 1 d . . .
O22 O 0.72843(11) 0.76795(3) 0.00405(16) 0.0279(2) Uani 1 1 d . . .
O23 O 0.11596(11) 0.73953(2) 0.01045(14) 0.0225(2) Uani 1 1 d . . .
O24 O 0.23059(11) 0.69490(3) 0.18750(16) 0.0275(2) Uani 1 1 d . . .
C21 C 0.71542(15) 0.73601(3) 0.04621(19) 0.0196(2) Uani 1 1 d . . .
C22 C 0.54925(15) 0.72017(3) 0.0843(2) 0.0209(3) Uani 1 1 d . . .
C23 C 0.40782(15) 0.73770(3) 0.04745(19) 0.0194(2) Uani 1 1 d . . .
C24 C 0.24034(14) 0.72221(3) 0.08750(18) 0.0184(2) Uani 1 1 d . . .
H21 H 0.964(3) 0.7256(7) 0.039(4) 0.075(8) Uiso 1 1 d . . .
H22 H 0.547(2) 0.6966(5) 0.135(3) 0.041(5) Uiso 1 1 d . . .
H23 H 0.409(2) 0.7618(5) -0.009(3) 0.032(4) Uiso 1 1 d . . .
O11 O 0.5227(10) 0.6682(2) 0.4633(11) 0.039(3) Uiso 0.155(4) 1 d P . .
H11 H 0.6027 0.6793 0.5030 0.058 Uiso 0.155(4) 1 d PR . .
H10 H 0.4660 0.6837 0.4141 0.058 Uiso 0.155(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 1.3589(15) . ?
N1 C3 1.3484(16) . ?
N1 C13 1.3981(16) . ?
N1 C5 1.4515(17) . ?
N2 C11 1.4091(15) . ?
N2 C16 1.4632(17) . ?
N2 C14 1.4797(17) . ?
N3 C17 1.4887(18) . ?
N3 C15 1.4915(17) . ?
N3 H1 0.910(18) . ?
N3 H2 0.880(19) . ?
O1 C1 1.2624(16) . ?
O2 C4 1.2044(19) . ?
O3 C4 1.3383(19) . ?
O3 H4 0.97(3) . ?
C1 C2 1.4318(19) . ?
C1 C8 1.4587(17) . ?
C2 C3 1.3719(19) . ?
C2 C4 1.4924(17) . ?
C3 H3 0.966(16) . ?
C5 C6 1.494(2) . ?
C5 C7 1.502(2) . ?
C5 H5 0.947(17) . ?
C6 C7 1.502(2) . ?
C6 H61 0.96(2) . ?
C6 H62 0.94(2) . ?
C7 H71 0.963(18) . ?
C7 H72 0.973(18) . ?
C8 C13 1.4052(17) . ?
C8 C9 1.4067(18) . ?
C9 C10 1.3607(17) . ?
C9 H9 0.969(17) . ?
C10 C11 1.4133(17) . ?
C11 C12 1.3847(17) . ?
C12 C13 1.4063(17) . ?
C12 H12 0.949(16) . ?
C14 C15 1.5123(18) . ?
C14 H141 1.000(18) . ?
C14 H142 0.987(17) . ?
C15 H151 0.969(17) . ?
C15 H152 0.962(19) . ?
C16 C17 1.5168(19) . ?
C16 H161 1.018(19) . ?
C16 H162 0.980(18) . ?
C17 H171 0.977(18) . ?
C17 H172 0.988(18) . ?
O21 C21 1.2945(15) . ?
O21 H21 1.13(3) . ?
O22 C21 1.2311(16) . ?
O23 C24 1.2827(15) . ?
O24 C24 1.2376(16) . ?
C21 C22 1.4922(17) . ?
C22 C23 1.3224(17) . ?
C22 H22 0.95(2) . ?
C23 C24 1.4995(16) . ?
C23 H23 0.981(18) . ?
O11 H11 0.7998 . ?
O11 H10 0.7999 . ?

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 119.93(11) . . ?
C3 N1 C5 119.42(11) . . ?
C13 N1 C5 120.25(10) . . ?
C11 N2 C16 116.03(10) . . ?
C11 N2 C14 114.76(10) . . ?
C16 N2 C14 110.60(10) . . ?
C17 N3 C15 110.81(10) . . ?
C17 N3 H1 111.3(11) . . ?
C15 N3 H1 106.4(11) . . ?
C17 N3 H2 107.3(11) . . ?
C15 N3 H2 110.5(12) . . ?
H1 N3 H2 110.6(16) . . ?
C4 O3 H4 104.7(15) . . ?
O1 C1 C2 123.19(12) . . ?
O1 C1 C8 121.35(12) . . ?
C2 C1 C8 115.46(11) . . ?
C3 C2 C1 120.75(11) . . ?
C3 C2 C4 117.74(12) . . ?
C1 C2 C4 121.50(12) . . ?
N1 C3 C2 123.30(12) . . ?
N1 C3 H3 115.8(9) . . ?
C2 C3 H3 120.9(9) . . ?
O2 C4 O3 121.95(13) . . ?
O2 C4 C2 123.65(14) . . ?
O3 C4 C2 114.40(13) . . ?
N1 C5 C6 118.24(12) . . ?
N1 C5 C7 120.22(12) . . ?
C6 C5 C7 60.19(10) . . ?
N1 C5 H5 112.1(10) . . ?
C6 C5 H5 118.7(10) . . ?
C7 C5 H5 118.4(10) . . ?
C5 C6 C7 60.18(9) . . ?
C5 C6 H61 115.6(12) . . ?
C7 C6 H61 118.1(12) . . ?
C5 C6 H62 116.9(11) . . ?
C7 C6 H62 117.8(11) . . ?
H61 C6 H62 116.4(16) . . ?
C5 C7 C6 59.63(9) . . ?
C5 C7 H71 117.6(10) . . ?
C6 C7 H71 117.4(10) . . ?
C5 C7 H72 116.3(11) . . ?
C6 C7 H72 118.7(11) . . ?
H71 C7 H72 115.6(15) . . ?
C13 C8 C9 118.96(11) . . ?
C13 C8 C1 121.02(12) . . ?
C9 C8 C1 120.02(11) . . ?
C10 C9 C8 119.21(12) . . ?
C10 C9 H9 120.7(10) . . ?
C8 C9 H9 120.0(10) . . ?
F1 C10 C9 118.78(11) . . ?
F1 C10 C11 117.87(11) . . ?
C9 C10 C11 123.33(12) . . ?
C12 C11 N2 123.01(11) . . ?
C12 C11 C10 117.39(11) . . ?
N2 C11 C10 119.55(11) . . ?
C11 C12 C13 120.63(12) . . ?
C11 C12 H12 119.1(9) . . ?
C13 C12 H12 120.3(9) . . ?
N1 C13 C8 119.49(11) . . ?
N1 C13 C12 120.05(11) . . ?
C8 C13 C12 120.45(11) . . ?
N2 C14 C15 110.37(11) . . ?
N2 C14 H141 108.2(10) . . ?
C15 C14 H141 110.4(10) . . ?
N2 C14 H142 109.9(10) . . ?
C15 C14 H142 108.9(10) . . ?
H141 C14 H142 109.1(14) . . ?
N3 C15 C14 109.73(11) . . ?
N3 C15 H151 109.4(10) . . ?
C14 C15 H151 110.9(10) . . ?
N3 C15 H152 107.1(11) . . ?
C14 C15 H152 111.3(11) . . ?
H151 C15 H152 108.3(15) . . ?
N2 C16 C17 109.61(11) . . ?
N2 C16 H161 113.0(10) . . ?
C17 C16 H161 108.0(10) . . ?
N2 C16 H162 109.4(11) . . ?
C17 C16 H162 107.4(11) . . ?
H161 C16 H162 109.3(15) . . ?
N3 C17 C16 110.25(11) . . ?
N3 C17 H171 106.9(10) . . ?
C16 C17 H171 110.9(11) . . ?
N3 C17 H172 108.1(10) . . ?
C16 C17 H172 111.1(10) . . ?
H171 C17 H172 109.4(15) . . ?
C21 O21 H21 114.3(13) . . ?
O22 C21 O21 125.08(11) . . ?
O22 C21 C22 120.76(11) . . ?
O21 C21 C22 114.16(11) . . ?
C23 C22 C21 122.27(12) . . ?
C23 C22 H22 120.0(12) . . ?
C21 C22 H22 117.7(12) . . ?
C22 C23 C24 122.69(12) . . ?
C22 C23 H23 120.5(10) . . ?
C24 C23 H23 116.8(10) . . ?
O24 C24 O23 125.43(11) . . ?
O24 C24 C23 120.19(11) . . ?
O23 C24 C23 114.38(11) . . ?
H11 O11 H10 101.9 . . ?

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 -179.60(12) . . . . ?
C8 C1 C2 C3 0.84(18) . . . . ?
O1 C1 C2 C4 1.77(19) . . . . ?
C8 C1 C2 C4 -177.79(11) . . . . ?
C13 N1 C3 C2 -1.06(19) . . . . ?
C5 N1 C3 C2 -173.78(12) . . . . ?
C1 C2 C3 N1 -0.7(2) . . . . ?
C4 C2 C3 N1 177.97(12) . . . . ?
C3 C2 C4 O2 -1.8(2) . . . . ?
C1 C2 C4 O2 176.86(13) . . . . ?
C3 C2 C4 O3 179.15(12) . . . . ?
C1 C2 C4 O3 -2.17(18) . . . . ?
C3 N1 C5 C6 -47.51(17) . . . . ?
C13 N1 C5 C6 139.80(13) . . . . ?
C3 N1 C5 C7 -117.62(14) . . . . ?
C13 N1 C5 C7 69.69(16) . . . . ?
N1 C5 C6 C7 -110.53(14) . . . . ?
N1 C5 C7 C6 107.30(14) . . . . ?
O1 C1 C8 C13 -178.83(12) . . . . ?
C2 C1 C8 C13 0.74(17) . . . . ?
O1 C1 C8 C9 0.40(19) . . . . ?
C2 C1 C8 C9 179.97(11) . . . . ?
C13 C8 C9 C10 1.60(19) . . . . ?
C1 C8 C9 C10 -177.65(11) . . . . ?
C8 C9 C10 F1 -178.93(11) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C16 N2 C11 C12 -12.13(18) . . . . ?
C14 N2 C11 C12 118.89(13) . . . . ?
C16 N2 C11 C10 165.04(12) . . . . ?
C14 N2 C11 C10 -63.94(16) . . . . ?
F1 C10 C11 C12 178.03(11) . . . . ?
C9 C10 C11 C12 -0.78(19) . . . . ?
F1 C10 C11 N2 0.70(18) . . . . ?
C9 C10 C11 N2 -178.10(12) . . . . ?
N2 C11 C12 C13 177.43(11) . . . . ?
C10 C11 C12 C13 0.20(18) . . . . ?
C3 N1 C13 C8 2.63(18) . . . . ?
C5 N1 C13 C8 175.28(11) . . . . ?
C3 N1 C13 C12 -176.91(11) . . . . ?
C5 N1 C13 C12 -4.26(18) . . . . ?
C9 C8 C13 N1 178.30(11) . . . . ?
C1 C8 C13 N1 -2.46(18) . . . . ?
C9 C8 C13 C12 -2.17(18) . . . . ?
C1 C8 C13 C12 177.07(11) . . . . ?
C11 C12 C13 N1 -179.21(11) . . . . ?
C11 C12 C13 C8 1.26(19) . . . . ?
C11 N2 C14 C15 166.68(11) . . . . ?
C16 N2 C14 C15 -59.73(15) . . . . ?
C17 N3 C15 C14 -56.40(15) . . . . ?
N2 C14 C15 N3 57.26(15) . . . . ?
C11 N2 C16 C17 -167.37(12) . . . . ?
C14 N2 C16 C17 59.68(15) . . . . ?
C15 N3 C17 C16 57.09(15) . . . . ?
N2 C16 C17 N3 -58.32(16) . . . . ?
O22 C21 C22 C23 10.3(2) . . . . ?
O21 C21 C22 C23 -169.46(13) . . . . ?
C21 C22 C23 C24 -179.22(12) . . . . ?
C22 C23 C24 O24 12.6(2) . . . . ?
C22 C23 C24 O23 -167.30(13) . . . . ?

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 H4 O1 0.97(3) 1.59(3) 2.5275(15) 160(2) .
N3 H1 O24 0.910(18) 1.886(18) 2.7856(15) 169.4(15) .
N3 H2 O22 0.880(19) 1.876(19) 2.7430(14) 167.9(17) 4_476
O21 H21 O23 1.13(3) 1.34(3) 2.4710(13) 179(3) 1_655
O11 H10 O24 0.80 2.44 3.118(8) 143.8 .
O11 H11 O22 0.80 2.21 2.898(8) 144.9 4_576

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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 1567145'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F N3 O3, C4 H3 O4, 2(H2 O)'
_chemical_formula_sum            'C20 H26 F N3 O9'
_chemical_formula_weight         471.44

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                   8.1127(8)
_cell_length_b                   9.6281(9)
_cell_length_c                   27.380(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.525(2)
_cell_angle_gamma                90.00
_cell_volume                     2134.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2414
_cell_measurement_theta_min      2.243
_cell_measurement_theta_max      24.252

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_T_max  0.9976
_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            17344
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3782
_reflns_number_gt                2776
_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)+(0.0359P)²+0.5280P] 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         3782
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.45170(13) 0.32054(11) 0.40320(4) 0.0259(3) Uani 1 1 d . . .
N1 N 0.83784(18) 0.69941(16) 0.50827(5) 0.0186(4) Uani 1 1 d . . .
N2 N 0.48395(19) 0.57663(16) 0.36307(5) 0.0189(4) Uani 1 1 d . . .
N3 N 0.3666(2) 0.64875(17) 0.26578(6) 0.0200(4) Uani 1 1 d . . .
H31 H 0.462(3) 0.688(2) 0.2509(8) 0.037(6) Uiso 1 1 d . . .
H32 H 0.274(3) 0.650(2) 0.2411(8) 0.036(6) Uiso 1 1 d . . .
O1 O 1.07918(19) 0.58224(17) 0.64054(5) 0.0378(4) Uani 1 1 d . . .
O2 O 0.99745(18) 0.36268(17) 0.62880(5) 0.0332(4) Uani 1 1 d . . .
H2 H 0.921(3) 0.310(3) 0.6017(11) 0.081(10) Uiso 1 1 d . . .
O3 O 0.81353(17) 0.29766(14) 0.55753(5) 0.0277(3) Uani 1 1 d . . .
C1 C 1.0028(2) 0.4952(2) 0.61588(7) 0.0266(5) Uani 1 1 d . . .
C2 C 0.9100(2) 0.5278(2) 0.56910(7) 0.0213(5) Uani 1 1 d . . .
C3 C 0.8189(2) 0.4230(2) 0.54286(7) 0.0207(4) Uani 1 1 d . . .
C4 C 0.8541(2) 0.84594(19) 0.49277(7) 0.0222(5) Uani 1 1 d . . .
H4A H 0.8681 0.8490 0.4571 0.027 Uiso 1 1 calc R . .
H4B H 0.9543 0.8866 0.5096 0.027 Uiso 1 1 calc R . .
C5 C 0.7054(3) 0.9325(2) 0.50417(8) 0.0295(5) Uani 1 1 d . . .
H5A H 0.7237 1.0293 0.4948 0.044 Uiso 1 1 calc R . .
H5B H 0.6893 0.9279 0.5393 0.044 Uiso 1 1 calc R . .
H5C H 0.6070 0.8965 0.4858 0.044 Uiso 1 1 calc R . .
C6 C 0.5302(2) 0.4923(2) 0.32079(7) 0.0214(5) Uani 1 1 d . . .
H6A H 0.5464 0.3943 0.3310 0.026 Uiso 1 1 calc R . .
H6B H 0.6353 0.5270 0.3089 0.026 Uiso 1 1 calc R . .
C7 C 0.3956(2) 0.5009(2) 0.28023(7) 0.0230(5) Uani 1 1 d . . .
H7A H 0.4284 0.4469 0.2516 0.028 Uiso 1 1 calc R . .
H7B H 0.2924 0.4603 0.2915 0.028 Uiso 1 1 calc R . .
C8 C 0.3313(2) 0.7371(2) 0.30862(6) 0.0208(5) Uani 1 1 d . . .
H8A H 0.2239 0.7097 0.3210 0.025 Uiso 1 1 calc R . .
H8B H 0.3232 0.8355 0.2982 0.025 Uiso 1 1 calc R . .
C9 C 0.4656(2) 0.72252(19) 0.34925(7) 0.0203(4) Uani 1 1 d . . .
H9A H 0.5713 0.7582 0.3381 0.024 Uiso 1 1 calc R . .
H9B H 0.4365 0.7779 0.3780 0.024 Uiso 1 1 calc R . .
C10 C 0.9149(2) 0.6604(2) 0.55079(7) 0.0210(5) Uani 1 1 d . . .
H10 H 0.9764 0.7283 0.5693 0.025 Uiso 1 1 calc R . .
C11 C 0.7427(2) 0.60326(19) 0.48028(6) 0.0168(4) Uani 1 1 d . . .
C12 C 0.7327(2) 0.46611(19) 0.49744(7) 0.0177(4) Uani 1 1 d . . .
C13 C 0.6353(2) 0.3699(2) 0.46979(7) 0.0194(4) Uani 1 1 d . . .
H13 H 0.6253 0.2769 0.4808 0.023 Uiso 1 1 calc R . .
C14 C 0.5560(2) 0.41115(19) 0.42733(7) 0.0186(4) Uani 1 1 d . . .
C15 C 0.5701(2) 0.54582(19) 0.40764(7) 0.0180(4) Uani 1 1 d . . .
C16 C 0.6628(2) 0.64128(19) 0.43537(6) 0.0173(4) Uani 1 1 d . . .
H16 H 0.6724 0.7338 0.4238 0.021 Uiso 1 1 calc R . .
O21 O 0.47277(17) 0.56379(16) 0.17003(5) 0.0292(4) Uani 1 1 d . . .
H21 H 0.350(4) 0.557(3) 0.1549(11) 0.087(10) Uiso 1 1 d . . .
O22 O 0.56788(16) 0.54758(15) 0.09532(5) 0.0279(4) Uani 1 1 d . . .
O23 O 1.08935(16) 0.63601(15) 0.20406(5) 0.0283(4) Uani 1 1 d . . .
O24 O 1.17748(16) 0.54137(14) 0.13571(5) 0.0250(3) Uani 1 1 d . . .
C21 C 0.5914(2) 0.5592(2) 0.13942(7) 0.0201(4) Uani 1 1 d . . .
C22 C 0.7588(2) 0.5721(2) 0.16438(7) 0.0221(5) Uani 1 1 d . . .
H22 H 0.7691 0.5797 0.1990 0.027 Uiso 1 1 calc R . .
C23 C 0.8928(2) 0.57334(19) 0.13969(7) 0.0204(4) Uani 1 1 d . . .
H23 H 0.8788 0.5662 0.1051 0.025 Uiso 1 1 calc R . .
C24 C 1.0661(2) 0.58512(19) 0.16181(7) 0.0194(4) Uani 1 1 d . . .
O11 O 0.5974(2) 0.84094(17) 0.23958(6) 0.0329(4) Uani 1 1 d . . .
H11 H 0.706(4) 0.806(3) 0.2495(12) 0.109(13) Uiso 1 1 d . . .
H12 H 0.593(3) 0.869(3) 0.2093(11) 0.070(10) Uiso 1 1 d . . .
O12 O 0.8959(2) 0.73852(18) 0.27491(6) 0.0377(4) Uani 1 1 d . . .
H14 H 0.953(4) 0.691(3) 0.2489(11) 0.093(11) Uiso 1 1 d . . .
H15 H 0.923(3) 0.701(3) 0.3044(11) 0.070(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 C14 1.358(2) . ?
N1 C10 1.341(2) . ?
N1 C11 1.402(2) . ?
N1 C4 1.481(2) . ?
N2 C15 1.400(2) . ?
N2 C9 1.460(2) . ?
N2 C6 1.481(2) . ?
N3 C8 1.491(2) . ?
N3 C7 1.493(3) . ?
N3 H31 0.97(2) . ?
N3 H32 0.98(2) . ?
O1 C1 1.221(3) . ?
O2 C1 1.326(3) . ?
O2 H2 1.07(3) . ?
O3 C3 1.274(2) . ?
C1 C2 1.479(3) . ?
C2 C10 1.373(3) . ?
C2 C3 1.419(3) . ?
C3 C12 1.449(3) . ?
C4 C5 1.515(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.511(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 0.9500 . ?
C11 C16 1.403(2) . ?
C11 C12 1.406(3) . ?
C12 C13 1.408(3) . ?
C13 C14 1.353(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.412(3) . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
O21 C21 1.315(2) . ?
O21 H21 1.06(3) . ?
O22 C21 1.216(2) . ?
O23 C24 1.260(2) . ?
O24 C24 1.259(2) . ?
C21 C22 1.487(3) . ?
C22 C23 1.315(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.501(3) . ?
C23 H23 0.9500 . ?
O11 H11 0.96(4) . ?
O11 H12 0.87(3) . ?
O12 H14 0.99(3) . ?
O12 H15 0.90(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
C10 N1 C11 120.05(16) . . ?
C10 N1 C4 118.07(16) . . ?
C11 N1 C4 121.87(15) . . ?
C15 N2 C9 117.86(15) . . ?
C15 N2 C6 115.36(15) . . ?
C9 N2 C6 110.60(15) . . ?
C8 N3 C7 111.75(15) . . ?
C8 N3 H31 107.6(13) . . ?
C7 N3 H31 111.6(13) . . ?
C8 N3 H32 111.0(12) . . ?
C7 N3 H32 107.1(12) . . ?
H31 N3 H32 107.6(17) . . ?
C1 O2 H2 107.6(15) . . ?
O1 C1 O2 122.47(19) . . ?
O1 C1 C2 123.2(2) . . ?
O2 C1 C2 114.33(19) . . ?
C10 C2 C3 120.11(18) . . ?
C10 C2 C1 119.26(19) . . ?
C3 C2 C1 120.62(19) . . ?
O3 C3 C2 122.72(18) . . ?
O3 C3 C12 121.18(18) . . ?
C2 C3 C12 116.09(17) . . ?
N1 C4 C5 112.26(16) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 109.77(15) . . ?
N2 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N3 C7 C6 110.01(16) . . ?
N3 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
N3 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C9 111.14(15) . . ?
N3 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N3 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C8 109.70(15) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N1 C10 C2 123.72(18) . . ?
N1 C10 H10 118.1 . . ?
C2 C10 H10 118.1 . . ?
N1 C11 C16 121.04(17) . . ?
N1 C11 C12 118.60(16) . . ?
C16 C11 C12 120.33(17) . . ?
C11 C12 C13 118.70(17) . . ?
C11 C12 C3 121.40(17) . . ?
C13 C12 C3 119.90(17) . . ?
C14 C13 C12 119.39(18) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 F1 118.59(17) . . ?
C13 C14 C15 123.52(18) . . ?
F1 C14 C15 117.84(16) . . ?
C16 C15 N2 124.23(17) . . ?
C16 C15 C14 117.03(17) . . ?
N2 C15 C14 118.66(16) . . ?
C15 C16 C11 120.91(17) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C21 O21 H21 117.3(16) . . ?
O22 C21 O21 124.02(18) . . ?
O22 C21 C22 123.17(18) . . ?
O21 C21 C22 112.80(16) . . ?
C23 C22 C21 121.66(18) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 125.24(18) . . ?
C22 C23 H23 117.4 . . ?
C24 C23 H23 117.4 . . ?
O24 C24 O23 125.41(17) . . ?
O24 C24 C23 115.66(17) . . ?
O23 C24 C23 118.93(17) . . ?
H11 O11 H12 111(3) . . ?
H14 O12 H15 111(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C10 3.1(3) . . . . ?
O2 C1 C2 C10 -176.29(17) . . . . ?
O1 C1 C2 C3 -177.87(19) . . . . ?
O2 C1 C2 C3 2.7(3) . . . . ?
C10 C2 C3 O3 178.18(17) . . . . ?
C1 C2 C3 O3 -0.8(3) . . . . ?
C10 C2 C3 C12 -0.9(3) . . . . ?
C1 C2 C3 C12 -179.93(16) . . . . ?
C10 N1 C4 C5 -99.3(2) . . . . ?
C11 N1 C4 C5 79.6(2) . . . . ?
C15 N2 C6 C7 161.54(16) . . . . ?
C9 N2 C6 C7 -61.5(2) . . . . ?
C8 N3 C7 C6 -54.3(2) . . . . ?
N2 C6 C7 N3 57.5(2) . . . . ?
C7 N3 C8 C9 53.8(2) . . . . ?
C15 N2 C9 C8 -163.97(15) . . . . ?
C6 N2 C9 C8 60.3(2) . . . . ?
N3 C8 C9 N2 -56.2(2) . . . . ?
C11 N1 C10 C2 1.4(3) . . . . ?
C4 N1 C10 C2 -179.74(17) . . . . ?
C3 C2 C10 N1 -0.4(3) . . . . ?
C1 C2 C10 N1 178.63(17) . . . . ?
C10 N1 C11 C16 -179.14(17) . . . . ?
C4 N1 C11 C16 2.0(3) . . . . ?
C10 N1 C11 C12 -1.0(3) . . . . ?
C4 N1 C11 C12 -179.81(16) . . . . ?
N1 C11 C12 C13 179.04(16) . . . . ?
C16 C11 C12 C13 -2.8(3) . . . . ?
N1 C11 C12 C3 -0.4(3) . . . . ?
C16 C11 C12 C3 177.81(17) . . . . ?
O3 C3 C12 C11 -177.85(17) . . . . ?
C2 C3 C12 C11 1.3(3) . . . . ?
O3 C3 C12 C13 2.8(3) . . . . ?
C2 C3 C12 C13 -178.10(17) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C3 C12 C13 C14 -179.71(17) . . . . ?
C12 C13 C14 F1 -174.59(16) . . . . ?
C12 C13 C14 C15 2.6(3) . . . . ?
C9 N2 C15 C16 -11.6(3) . . . . ?
C6 N2 C15 C16 122.1(2) . . . . ?
C9 N2 C15 C14 164.96(17) . . . . ?
C6 N2 C15 C14 -61.3(2) . . . . ?
C13 C14 C15 C16 -4.0(3) . . . . ?
F1 C14 C15 C16 173.22(16) . . . . ?
C13 C14 C15 N2 179.20(17) . . . . ?
F1 C14 C15 N2 -3.6(2) . . . . ?
N2 C15 C16 C11 178.55(17) . . . . ?
C14 C15 C16 C11 1.9(3) . . . . ?
N1 C11 C16 C15 179.47(16) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
O22 C21 C22 C23 0.8(3) . . . . ?
O21 C21 C22 C23 -178.25(18) . . . . ?
C21 C22 C23 C24 -179.62(17) . . . . ?
C22 C23 C24 O24 158.32(19) . . . . ?
C22 C23 C24 O23 -21.4(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
O2 H2 O3 1.07(3) 1.45(3) 2.463(2) 156(3) .
N3 H31 O11 0.97(2) 1.87(2) 2.758(2) 150.0(18) .
N3 H32 O23 0.98(2) 1.76(2) 2.732(2) 170.5(19) 1_455
O21 H21 O24 1.06(3) 1.47(3) 2.5282(18) 177(3) 1_455
O11 H11 O12 0.96(4) 1.78(4) 2.736(2) 173(3) .
O11 H12 O1 0.87(3) 1.94(3) 2.806(2) 176(3) 4_575
O12 H14 O23 0.99(3) 1.78(3) 2.752(2) 167(3) .
O12 H15 O2 0.90(3) 2.00(3) 2.893(2) 173(3) 3_766

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.194
_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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1567144'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H19 F N3 O3), C4 H2 O4, 2(H2 O)'
_chemical_formula_sum            'C36 H44 F2 N6 O12'
_chemical_formula_weight         790.77

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                   6.7869(4)
_cell_length_b                   9.3544(6)
_cell_length_c                   15.7300(9)
_cell_angle_alpha                93.6351(9)
_cell_angle_beta                 92.6297(9)
_cell_angle_gamma                110.9168(9)
_cell_volume                     928.45(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5555
_cell_measurement_theta_min      2.339
_cell_measurement_theta_max      30.586

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  0.9832
_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            10525
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         29.00
_reflns_number_total             4924
_reflns_number_gt                4275
_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)+(0.0576P)²+0.2112P] 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         4924
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.47754(10) 0.45281(6) 0.39767(4) 0.02441(15) Uani 1 1 d . . .
O1 O 0.09547(14) -0.38115(10) 0.62947(6) 0.0319(2) Uani 1 1 d . . .
O2 O 0.26627(13) -0.15513(10) 0.70231(5) 0.02678(18) Uani 1 1 d . . .
H2 H 0.320(3) -0.049(2) 0.6880(13) 0.063(6) Uiso 1 1 d . . .
O3 O 0.36892(12) 0.08804(9) 0.62661(5) 0.02219(16) Uani 1 1 d . . .
N1 N 0.07738(13) -0.17237(9) 0.40497(5) 0.01512(16) Uani 1 1 d . . .
N2 N 0.29483(13) 0.28633(9) 0.24754(5) 0.01710(17) Uani 1 1 d . . .
N3 N 0.31196(14) 0.43927(10) 0.09671(5) 0.01851(17) Uani 1 1 d . . .
H31 H 0.288(2) 0.5228(19) 0.0717(10) 0.041(4) Uiso 1 1 d . . .
H32 H 0.357(2) 0.3856(17) 0.0571(9) 0.030(4) Uiso 1 1 d . . .
C1 C 0.17395(16) -0.24217(12) 0.63063(7) 0.0222(2) Uani 1 1 d . . .
C2 C 0.17846(15) -0.15635(11) 0.55407(6) 0.01704(19) Uani 1 1 d . . .
C3 C 0.28159(14) 0.00707(11) 0.55808(6) 0.01596(18) Uani 1 1 d . . .
C4 C -0.02612(16) -0.27295(11) 0.32681(7) 0.0196(2) Uani 1 1 d . . .
C5 C 0.1338(2) -0.31430(13) 0.27620(7) 0.0276(2) Uani 1 1 d . . .
C6 C 0.50105(15) 0.37765(11) 0.21840(6) 0.01839(19) Uani 1 1 d . . .
C7 C 0.47753(16) 0.50543(11) 0.16915(7) 0.0196(2) Uani 1 1 d . . .
C8 C 0.10799(16) 0.33121(11) 0.12448(6) 0.01922(19) Uani 1 1 d . . .
C9 C 0.14369(16) 0.20890(11) 0.17514(6) 0.01782(19) Uani 1 1 d . . .
C10 C 0.08263(15) -0.23749(11) 0.47823(6) 0.01734(19) Uani 1 1 d . . .
C11 C 0.18040(14) -0.01450(10) 0.40203(6) 0.01338(17) Uani 1 1 d . . .
C12 C 0.28189(14) 0.07539(10) 0.47771(6) 0.01377(18) Uani 1 1 d . . .
C13 C 0.38457(15) 0.23504(11) 0.47471(6) 0.01604(18) Uani 1 1 d . . .
C14 C 0.38558(15) 0.29834(10) 0.39935(6) 0.01636(18) Uani 1 1 d . . .
C15 C 0.28994(14) 0.21083(10) 0.32142(6) 0.01474(18) Uani 1 1 d . . .
C16 C 0.18544(14) 0.05378(10) 0.32439(6) 0.01457(18) Uani 1 1 d . . .
H10 H 0.016(2) -0.3448(16) 0.4743(8) 0.025(3) Uiso 1 1 d . . .
H13 H 0.451(2) 0.2961(17) 0.5252(9) 0.032(4) Uiso 1 1 d . . .
H16 H 0.124(2) -0.0057(15) 0.2713(9) 0.022(3) Uiso 1 1 d . . .
H41 H -0.103(2) -0.2217(15) 0.2947(8) 0.023(3) Uiso 1 1 d . . .
H42 H -0.130(2) -0.3623(16) 0.3475(9) 0.024(3) Uiso 1 1 d . . .
H51 H 0.198(3) -0.3780(19) 0.3083(10) 0.041(4) Uiso 1 1 d . . .
H52 H 0.062(3) -0.3726(19) 0.2231(11) 0.042(4) Uiso 1 1 d . . .
H53 H 0.244(3) -0.2240(19) 0.2598(10) 0.037(4) Uiso 1 1 d . . .
H61 H 0.602(2) 0.4202(15) 0.2674(8) 0.021(3) Uiso 1 1 d . . .
H62 H 0.552(2) 0.3070(16) 0.1808(9) 0.024(3) Uiso 1 1 d . . .
H71 H 0.435(2) 0.5737(16) 0.2056(9) 0.023(3) Uiso 1 1 d . . .
H72 H 0.610(2) 0.5606(16) 0.1459(9) 0.024(3) Uiso 1 1 d . . .
H81 H 0.050(2) 0.3906(16) 0.1622(9) 0.024(3) Uiso 1 1 d . . .
H82 H 0.018(2) 0.2870(15) 0.0726(9) 0.025(3) Uiso 1 1 d . . .
H91 H 0.007(2) 0.1468(16) 0.1966(9) 0.026(3) Uiso 1 1 d . . .
H92 H 0.194(2) 0.1414(15) 0.1390(8) 0.021(3) Uiso 1 1 d . . .
O21 O 0.23702(12) 0.69211(8) 0.04637(5) 0.02481(17) Uani 1 1 d . . .
O22 O 0.57198(12) 0.75339(8) 0.01313(5) 0.02310(17) Uani 1 1 d . . .
C21 C 0.40962(16) 0.78555(11) 0.02512(6) 0.01787(19) Uani 1 1 d . . .
C22 C 0.41737(16) 0.94593(11) 0.01341(7) 0.0203(2) Uani 1 1 d . . .
H22 H 0.293(2) 0.9663(17) 0.0244(9) 0.033(4) Uiso 1 1 d . . .
O11 O 0.94769(16) 0.82291(12) 0.12373(6) 0.0381(2) Uani 1 1 d . . .
H11 H 0.838(3) 0.810(2) 0.0853(13) 0.058(5) Uiso 1 1 d . . .
H12 H 1.023(3) 0.767(2) 0.0950(13) 0.071(6) 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 C14 1.3567(10) . ?
O1 C1 1.2148(13) . ?
O2 C1 1.3346(14) . ?
O2 H2 0.98(2) . ?
O3 C3 1.2666(12) . ?
N1 C10 1.3420(12) . ?
N1 C11 1.3951(11) . ?
N1 C4 1.4807(12) . ?
N2 C15 1.3933(12) . ?
N2 C9 1.4600(12) . ?
N2 C6 1.4675(12) . ?
N3 C7 1.4969(13) . ?
N3 C8 1.4971(13) . ?
N3 H31 0.956(17) . ?
N3 H32 0.908(16) . ?
C1 C2 1.4847(13) . ?
C2 C10 1.3725(14) . ?
C2 C3 1.4320(13) . ?
C3 C12 1.4521(13) . ?
C4 C5 1.5169(15) . ?
C4 H41 0.970(14) . ?
C4 H42 0.967(14) . ?
C5 H51 1.001(17) . ?
C5 H52 0.975(17) . ?
C5 H53 0.966(16) . ?
C6 C7 1.5155(13) . ?
C6 H61 0.970(13) . ?
C6 H62 1.020(14) . ?
C7 H71 0.957(14) . ?
C7 H72 0.965(14) . ?
C8 C9 1.5161(13) . ?
C8 H81 0.977(14) . ?
C8 H82 0.971(14) . ?
C9 H91 0.990(14) . ?
C9 H92 0.982(13) . ?
C10 H10 0.939(14) . ?
C11 C12 1.4081(12) . ?
C11 C16 1.4099(13) . ?
C12 C13 1.4096(12) . ?
C13 C14 1.3575(13) . ?
C13 H13 0.941(15) . ?
C14 C15 1.4193(13) . ?
C15 C16 1.3897(12) . ?
C16 H16 0.962(14) . ?
O21 C21 1.2609(12) . ?
O22 C21 1.2605(12) . ?
C21 C22 1.5057(13) . ?
C22 C22 1.322(2) 2_675 ?
C22 H22 0.950(15) . ?
O11 H11 0.90(2) . ?
O11 H12 0.96(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 O2 H2 107.2(11) . . ?
C10 N1 C11 120.18(8) . . ?
C10 N1 C4 118.53(8) . . ?
C11 N1 C4 121.14(8) . . ?
C15 N2 C9 119.12(8) . . ?
C15 N2 C6 118.58(8) . . ?
C9 N2 C6 110.93(8) . . ?
C7 N3 C8 112.75(8) . . ?
C7 N3 H31 107.7(9) . . ?
C8 N3 H31 109.7(10) . . ?
C7 N3 H32 109.9(9) . . ?
C8 N3 H32 107.2(9) . . ?
H31 N3 H32 109.6(13) . . ?
O1 C1 O2 121.42(9) . . ?
O1 C1 C2 123.63(10) . . ?
O2 C1 C2 114.94(9) . . ?
C10 C2 C3 120.16(9) . . ?
C10 C2 C1 118.44(9) . . ?
C3 C2 C1 121.39(9) . . ?
O3 C3 C2 122.86(9) . . ?
O3 C3 C12 121.54(9) . . ?
C2 C3 C12 115.59(8) . . ?
N1 C4 C5 111.02(9) . . ?
N1 C4 H41 108.0(8) . . ?
C5 C4 H41 113.5(8) . . ?
N1 C4 H42 104.5(8) . . ?
C5 C4 H42 112.0(8) . . ?
H41 C4 H42 107.3(11) . . ?
C4 C5 H51 111.8(9) . . ?
C4 C5 H52 108.3(10) . . ?
H51 C5 H52 108.9(13) . . ?
C4 C5 H53 111.7(9) . . ?
H51 C5 H53 109.9(13) . . ?
H52 C5 H53 106.0(13) . . ?
N2 C6 C7 109.09(8) . . ?
N2 C6 H61 109.5(8) . . ?
C7 C6 H61 110.3(8) . . ?
N2 C6 H62 108.5(8) . . ?
C7 C6 H62 111.0(8) . . ?
H61 C6 H62 108.4(11) . . ?
N3 C7 C6 109.96(8) . . ?
N3 C7 H71 108.3(8) . . ?
C6 C7 H71 110.4(8) . . ?
N3 C7 H72 108.4(8) . . ?
C6 C7 H72 109.3(8) . . ?
H71 C7 H72 110.4(11) . . ?
N3 C8 C9 111.17(8) . . ?
N3 C8 H81 107.8(8) . . ?
C9 C8 H81 107.5(8) . . ?
N3 C8 H82 106.1(8) . . ?
C9 C8 H82 111.8(8) . . ?
H81 C8 H82 112.5(11) . . ?
N2 C9 C8 107.88(8) . . ?
N2 C9 H91 109.2(8) . . ?
C8 C9 H91 108.0(8) . . ?
N2 C9 H92 111.7(8) . . ?
C8 C9 H92 110.9(8) . . ?
H91 C9 H92 109.0(11) . . ?
N1 C10 C2 123.68(9) . . ?
N1 C10 H10 115.1(8) . . ?
C2 C10 H10 121.3(8) . . ?
N1 C11 C12 118.91(8) . . ?
N1 C11 C16 120.61(8) . . ?
C12 C11 C16 120.48(8) . . ?
C11 C12 C13 118.80(8) . . ?
C11 C12 C3 121.39(8) . . ?
C13 C12 C3 119.80(8) . . ?
C14 C13 C12 119.63(9) . . ?
C14 C13 H13 121.1(9) . . ?
C12 C13 H13 119.3(9) . . ?
F1 C14 C13 119.22(8) . . ?
F1 C14 C15 117.64(8) . . ?
C13 C14 C15 123.12(8) . . ?
C16 C15 N2 123.45(8) . . ?
C16 C15 C14 117.40(8) . . ?
N2 C15 C14 119.05(8) . . ?
C15 C16 C11 120.54(8) . . ?
C15 C16 H16 117.3(8) . . ?
C11 C16 H16 122.1(8) . . ?
O22 C21 O21 124.67(9) . . ?
O22 C21 C22 118.96(9) . . ?
O21 C21 C22 116.37(9) . . ?
C22 C22 C21 123.46(12) 2_675 . ?
C22 C22 H22 120.1(9) 2_675 . ?
C21 C22 H22 116.4(9) . . ?
H11 O11 H12 102.1(17) . . ?

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 C10 2.29(15) . . . . ?
O2 C1 C2 C10 -178.60(8) . . . . ?
O1 C1 C2 C3 -177.09(9) . . . . ?
O2 C1 C2 C3 2.03(14) . . . . ?
C10 C2 C3 O3 178.59(9) . . . . ?
C1 C2 C3 O3 -2.04(15) . . . . ?
C10 C2 C3 C12 -1.95(13) . . . . ?
C1 C2 C3 C12 177.42(8) . . . . ?
C10 N1 C4 C5 -93.84(10) . . . . ?
C11 N1 C4 C5 81.75(11) . . . . ?
C15 N2 C6 C7 -152.22(8) . . . . ?
C9 N2 C6 C7 64.49(10) . . . . ?
C8 N3 C7 C6 51.63(11) . . . . ?
N2 C6 C7 N3 -56.42(10) . . . . ?
C7 N3 C8 C9 -52.35(11) . . . . ?
C15 N2 C9 C8 153.10(8) . . . . ?
C6 N2 C9 C8 -63.83(10) . . . . ?
N3 C8 C9 N2 56.72(10) . . . . ?
C11 N1 C10 C2 2.74(14) . . . . ?
C4 N1 C10 C2 178.38(9) . . . . ?
C3 C2 C10 N1 -0.38(15) . . . . ?
C1 C2 C10 N1 -179.76(8) . . . . ?
C10 N1 C11 C12 -2.55(13) . . . . ?
C4 N1 C11 C12 -178.08(8) . . . . ?
C10 N1 C11 C16 176.58(8) . . . . ?
C4 N1 C11 C16 1.06(13) . . . . ?
N1 C11 C12 C13 -179.54(8) . . . . ?
C16 C11 C12 C13 1.32(13) . . . . ?
N1 C11 C12 C3 0.14(13) . . . . ?
C16 C11 C12 C3 -178.99(8) . . . . ?
O3 C3 C12 C11 -178.50(8) . . . . ?
C2 C3 C12 C11 2.04(13) . . . . ?
O3 C3 C12 C13 1.18(14) . . . . ?
C2 C3 C12 C13 -178.28(8) . . . . ?
C11 C12 C13 C14 -0.70(14) . . . . ?
C3 C12 C13 C14 179.61(8) . . . . ?
C12 C13 C14 F1 177.43(8) . . . . ?
C12 C13 C14 C15 -1.03(15) . . . . ?
C9 N2 C15 C16 15.89(14) . . . . ?
C6 N2 C15 C16 -124.39(10) . . . . ?
C9 N2 C15 C14 -160.37(9) . . . . ?
C6 N2 C15 C14 59.36(12) . . . . ?
F1 C14 C15 C16 -176.39(8) . . . . ?
C13 C14 C15 C16 2.08(14) . . . . ?
F1 C14 C15 N2 0.09(13) . . . . ?
C13 C14 C15 N2 178.56(9) . . . . ?
N2 C15 C16 C11 -177.72(8) . . . . ?
C14 C15 C16 C11 -1.41(13) . . . . ?
N1 C11 C16 C15 -179.35(8) . . . . ?
C12 C11 C16 C15 -0.24(14) . . . . ?
O22 C21 C22 C22 3.76(19) . . . 2_675 ?
O21 C21 C22 C22 -176.03(13) . . . 2_675 ?

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
O2 H2 O3 0.98(2) 1.60(2) 2.5230(11) 156.0(18) .
N3 H31 O21 0.956(17) 1.803(17) 2.7459(11) 168.4(14) .
N3 H32 O22 0.908(16) 1.858(16) 2.7563(11) 170.0(14) 2_665
O11 H11 O22 0.90(2) 1.97(2) 2.8665(13) 170.4(18) .
O11 H12 O21 0.96(2) 1.99(2) 2.9291(13) 166.9(18) 1_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1567678'
_audit_update_record             
;
2017-08-09 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Norfloxacin hemifumarate monohydrate '
_chemical_formula_moiety         'C16 H19 F N3 O3, H2 O, C4 H3 O4'
_chemical_formula_sum            'C20 H24 F N3 O8'
_chemical_formula_weight         453.42
_chemical_melting_point          502.2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6277(4)
_cell_length_b                   7.3695(2)
_cell_length_c                   17.1695(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.1910(10)
_cell_angle_gamma                90
_cell_volume                     2070.72(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.067
_cell_measurement_theta_min      2.410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1670 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.8899.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             952
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.126
_diffrn_reflns_theta_min         1.244
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3892
_reflns_number_total             4578
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+1.0492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C10(H10A,H10B), C11(H11A,H11B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O0AA(H0AA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43213(5) 0.61824(11) 0.49691(4) 0.02087(19) Uani 1 1 d . . . . .
O1 O 0.69946(6) 0.56792(15) 0.89472(6) 0.0250(2) Uani 1 1 d . . . . .
H1 H 0.6938 0.5668 0.8451 0.038 Uiso 1 1 calc GR . . . .
O1S O 0.05107(8) 0.29218(16) 0.45409(7) 0.0372(3) Uani 1 1 d . . . . .
H1SA H 0.0562 0.2026 0.4876 0.056 Uiso 1 1 d G . . . .
H1SB H 0.0118 0.2683 0.4147 0.056 Uiso 1 1 d G . . . .
O2 O 0.61892(6) 0.56897(15) 0.98508(6) 0.0283(2) Uani 1 1 d . . . . .
O0AA O 0.09146(6) 1.48090(12) 0.21312(5) 0.0205(2) Uani 1 1 d . . . . .
H0AA H 0.0863 1.5919 0.2022 0.031 Uiso 1 1 calc GR . . . .
O4 O 0.10417(6) 0.85330(13) 0.31189(5) 0.0217(2) Uani 1 1 d . . . . .
O5 O 0.07349(6) 0.80825(12) 0.18138(5) 0.0202(2) Uani 1 1 d . . . . .
O6 O 0.06409(6) 1.45152(13) 0.08119(6) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.13316(6) 0.59405(15) 0.42067(6) 0.0158(2) Uani 1 1 d . . . . .
H1A H 0.1034 0.5026 0.4371 0.019 Uiso 1 1 calc R . . . .
H1B H 0.1037 0.6412 0.3755 0.019 Uiso 1 1 calc R . . . .
N2 N 0.41033(7) 0.59012(15) 0.81295(6) 0.0156(2) Uani 1 1 d . . . . .
O3 O 0.63627(6) 0.55784(14) 0.74857(6) 0.0221(2) Uani 1 1 d . . . . .
C1 C 0.21107(8) 0.51874(18) 0.40321(7) 0.0172(3) Uani 1 1 d . . . . .
H1C H 0.2389 0.6118 0.3760 0.021 Uiso 1 1 calc R . . . .
H1D H 0.1992 0.4132 0.3674 0.021 Uiso 1 1 calc R . . . .
C2 C 0.26675(8) 0.46054(18) 0.47863(8) 0.0177(3) Uani 1 1 d . . . . .
H2A H 0.2416 0.3584 0.5031 0.021 Uiso 1 1 calc R . . . .
H2B H 0.3197 0.4188 0.4663 0.021 Uiso 1 1 calc R . . . .
N3 N 0.28020(6) 0.61449(15) 0.53414(6) 0.0145(2) Uani 1 1 d . . . . .
C4 C 0.34840(8) 0.60071(17) 0.59477(7) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.34378(8) 0.59737(17) 0.67451(7) 0.0150(3) Uani 1 1 d . . . . .
H5 H 0.2918 0.6000 0.6903 0.018 Uiso 1 1 calc R . . . .
C6 C 0.41518(8) 0.59014(17) 0.73253(7) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.47868(8) 0.58174(17) 0.86739(8) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.4735 0.5817 0.9216 0.020 Uiso 1 1 calc R . . . .
C8 C 0.55571(8) 0.57319(17) 0.84941(8) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.62631(9) 0.56894(18) 0.91585(8) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.14676(8) 0.73848(18) 0.48282(8) 0.0181(3) Uani 1 1 d . . . . .
H10A H 0.0937 0.7745 0.4966 0.022 Uiso 1 1 calc R . . . .
H10B H 0.1710 0.8467 0.4618 0.022 Uiso 1 1 calc R . . . .
C11 C 0.20307(8) 0.67190(19) 0.55640(8) 0.0167(3) Uani 1 1 d . . . . .
H11A H 0.2132 0.7704 0.5962 0.020 Uiso 1 1 calc R . . . .
H11B H 0.1776 0.5687 0.5799 0.020 Uiso 1 1 calc R . . . .
C12 C 0.42714(8) 0.59973(18) 0.57455(7) 0.0161(3) Uani 1 1 d . . . . .
C13 C 0.49699(8) 0.58856(17) 0.62900(8) 0.0164(3) Uani 1 1 d . . . . .
H13 H 0.5486 0.5856 0.6125 0.020 Uiso 1 1 calc R . . . .
C14 C 0.49234(8) 0.58142(17) 0.71006(7) 0.0149(3) Uani 1 1 d . . . . .
C15 C 0.56708(8) 0.56991(17) 0.76865(8) 0.0163(3) Uani 1 1 d . . . . .
C16 C 0.33024(8) 0.59711(19) 0.83942(8) 0.0181(3) Uani 1 1 d . . . . .
H16A H 0.2943 0.6843 0.8059 0.022 Uiso 1 1 calc R . . . .
H16B H 0.3384 0.6420 0.8946 0.022 Uiso 1 1 calc R . . . .
C17 C 0.28847(8) 0.4140(2) 0.83528(8) 0.0213(3) Uani 1 1 d . . . . .
H17A H 0.2770 0.3724 0.7802 0.032 Uiso 1 1 calc GR . . . .
H17B H 0.2371 0.4247 0.8554 0.032 Uiso 1 1 calc GR . . . .
H17C H 0.3242 0.3264 0.8675 0.032 Uiso 1 1 calc GR . . . .
C18 C 0.07669(8) 1.38632(17) 0.14804(8) 0.0162(3) Uani 1 1 d . . . . .
C19 C 0.07642(8) 1.18627(17) 0.15993(8) 0.0156(3) Uani 1 1 d . . . . .
H19 H 0.0714 1.1100 0.1147 0.019 Uiso 1 1 calc R . . . .
C20 C 0.08277(8) 1.10943(16) 0.23043(8) 0.0150(3) Uani 1 1 d . . . . .
H20 H 0.0851 1.1856 0.2754 0.018 Uiso 1 1 calc R . . . .
C21 C 0.08647(7) 0.90845(17) 0.24274(7) 0.0143(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.3572(14) . ?
O1 H1 0.8400 . ?
O1 C9 1.3294(17) . ?
O1S H1SA 0.8702 . ?
O1S H1SB 0.8700 . ?
O2 C9 1.2163(17) . ?
O0AA H0AA 0.8400 . ?
O0AA C18 1.3028(16) . ?
O4 C21 1.2401(15) . ?
O5 C21 1.2732(16) . ?
O6 C18 1.2277(16) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.4877(17) . ?
N1 C10 1.4958(17) . ?
N2 C6 1.3973(16) . ?
N2 C7 1.3392(16) . ?
N2 C16 1.4822(17) . ?
O3 C15 1.2613(16) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.5146(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N3 1.4731(16) . ?
N3 C4 1.4008(16) . ?
N3 C11 1.4640(16) . ?
C4 C5 1.3849(18) . ?
C4 C12 1.4127(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4093(17) . ?
C6 C14 1.4051(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3709(19) . ?
C8 C9 1.4854(18) . ?
C8 C15 1.4325(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5148(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3585(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.4084(18) . ?
C14 C15 1.4564(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.513(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.4885(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3236(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.4958(17) . ?

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
C9 O1 H1 109.5 . . ?
H1SA O1S H1SB 109.5 . . ?
C18 O0AA H0AA 109.5 . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 H1A 109.1 . . ?
C1 N1 H1B 109.1 . . ?
C1 N1 C10 112.46(10) . . ?
C10 N1 H1A 109.1 . . ?
C10 N1 H1B 109.1 . . ?
C6 N2 C16 121.01(10) . . ?
C7 N2 C6 119.96(11) . . ?
C7 N2 C16 119.03(11) . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 C2 110.84(10) . . ?
H1C C1 H1D 108.1 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N3 C2 C1 109.57(10) . . ?
N3 C2 H2A 109.8 . . ?
N3 C2 H2B 109.8 . . ?
C4 N3 C2 115.80(10) . . ?
C4 N3 C11 117.28(10) . . ?
C11 N3 C2 110.60(10) . . ?
N3 C4 C12 118.78(11) . . ?
C5 C4 N3 123.82(11) . . ?
C5 C4 C12 117.31(11) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.81(12) . . ?
C6 C5 H5 119.6 . . ?
N2 C6 C5 120.64(12) . . ?
N2 C6 C14 119.11(11) . . ?
C14 C6 C5 120.24(11) . . ?
N2 C7 H7 118.1 . . ?
N2 C7 C8 123.80(12) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.10(12) . . ?
C7 C8 C15 120.48(12) . . ?
C15 C8 C9 121.42(12) . . ?
O1 C9 C8 115.31(12) . . ?
O2 C9 O1 121.47(12) . . ?
O2 C9 C8 123.21(13) . . ?
N1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
N1 C10 C11 110.95(11) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N3 C11 C10 108.46(10) . . ?
N3 C11 H11A 110.0 . . ?
N3 C11 H11B 110.0 . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
F1 C12 C4 117.47(11) . . ?
F1 C12 C13 119.25(11) . . ?
C13 C12 C4 123.22(12) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.51(12) . . ?
C14 C13 H13 120.2 . . ?
C6 C14 C13 118.82(11) . . ?
C6 C14 C15 121.47(12) . . ?
C13 C14 C15 119.70(12) . . ?
O3 C15 C8 123.28(12) . . ?
O3 C15 C14 121.56(12) . . ?
C8 C15 C14 115.15(12) . . ?
N2 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
N2 C16 C17 112.60(11) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O0AA C18 C19 114.64(11) . . ?
O6 C18 O0AA 124.58(12) . . ?
O6 C18 C19 120.77(12) . . ?
C18 C19 H19 118.4 . . ?
C20 C19 C18 123.19(12) . . ?
C20 C19 H19 118.4 . . ?
C19 C20 H20 118.4 . . ?
C19 C20 C21 123.19(12) . . ?
C21 C20 H20 118.4 . . ?
O4 C21 O5 125.37(12) . . ?
O4 C21 C20 117.16(11) . . ?
O5 C21 C20 117.43(11) . . ?

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
F1 C12 C13 C14 175.83(11) . . . . ?
O0AA C18 C19 C20 6.20(19) . . . . ?
O6 C18 C19 C20 -174.12(13) . . . . ?
N1 C1 C2 N3 -55.49(14) . . . . ?
N1 C10 C11 N3 57.47(14) . . . . ?
N2 C6 C14 C13 -177.58(11) . . . . ?
N2 C6 C14 C15 0.84(18) . . . . ?
N2 C7 C8 C9 178.54(12) . . . . ?
N2 C7 C8 C15 -1.0(2) . . . . ?
C1 N1 C10 C11 -52.86(14) . . . . ?
C1 C2 N3 C4 -161.02(11) . . . . ?
C1 C2 N3 C11 62.46(13) . . . . ?
C2 N3 C4 C5 -118.34(13) . . . . ?
C2 N3 C4 C12 65.18(15) . . . . ?
C2 N3 C11 C10 -63.07(13) . . . . ?
N3 C4 C5 C6 -177.59(12) . . . . ?
N3 C4 C12 F1 2.07(17) . . . . ?
N3 C4 C12 C13 179.38(12) . . . . ?
C4 N3 C11 C10 161.13(11) . . . . ?
C4 C5 C6 N2 178.83(11) . . . . ?
C4 C5 C6 C14 -1.66(19) . . . . ?
C4 C12 C13 C14 -1.4(2) . . . . ?
C5 C4 C12 F1 -174.64(11) . . . . ?
C5 C4 C12 C13 2.66(19) . . . . ?
C5 C6 C14 C13 2.91(18) . . . . ?
C5 C6 C14 C15 -178.67(12) . . . . ?
C6 N2 C7 C8 0.11(19) . . . . ?
C6 N2 C16 C17 79.95(14) . . . . ?
C6 C14 C15 O3 178.33(12) . . . . ?
C6 C14 C15 C8 -1.61(18) . . . . ?
C7 N2 C6 C5 179.47(12) . . . . ?
C7 N2 C6 C14 -0.04(18) . . . . ?
C7 N2 C16 C17 -99.34(14) . . . . ?
C7 C8 C9 O1 -177.44(12) . . . . ?
C7 C8 C9 O2 1.5(2) . . . . ?
C7 C8 C15 O3 -178.28(12) . . . . ?
C7 C8 C15 C14 1.65(18) . . . . ?
C9 C8 C15 O3 2.2(2) . . . . ?
C9 C8 C15 C14 -177.86(11) . . . . ?
C10 N1 C1 C2 51.58(14) . . . . ?
C11 N3 C4 C5 15.21(18) . . . . ?
C11 N3 C4 C12 -161.27(12) . . . . ?
C12 C4 C5 C6 -1.06(18) . . . . ?
C12 C13 C14 C6 -1.40(19) . . . . ?
C12 C13 C14 C15 -179.85(12) . . . . ?
C13 C14 C15 O3 -3.26(19) . . . . ?
C13 C14 C15 C8 176.80(11) . . . . ?
C15 C8 C9 O1 2.08(18) . . . . ?
C15 C8 C9 O2 -178.93(13) . . . . ?
C16 N2 C6 C5 0.19(18) . . . . ?
C16 N2 C6 C14 -179.33(11) . . . . ?
C16 N2 C7 C8 179.41(12) . . . . ?
C18 C19 C20 C21 -177.01(12) . . . . ?
C19 C20 C21 O4 169.86(12) . . . . ?
C19 C20 C21 O5 -8.21(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/water '
