# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 F N3 O4'
_chemical_formula_weight         390.43

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

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

_cell_length_a                   8.9553(13)
_cell_length_b                   9.9570(14)
_cell_length_c                   12.2938(17)
_cell_angle_alpha                107.762(2)
_cell_angle_beta                 97.915(2)
_cell_angle_gamma                98.959(2)
_cell_volume                     1011.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1419
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      23.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             414
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8074
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.15
_reflns_number_total             3590
_reflns_number_gt                2138
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker apex II'
_computing_cell_refinement       'Bruker apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3590
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2346
_refine_ls_wR_factor_gt          0.2002
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_restrained_S_all      1.299
_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 0.1976(3) -0.4479(3) 0.4484(2) 0.1118(10) Uani 1 1 d . . .
N1 N 0.2136(3) 0.1988(3) 1.1017(2) 0.0509(7) Uani 1 1 d . . .
H1 H 0.1376 0.1259 1.0798 0.061 Uiso 1 1 calc R . .
N2 N 0.4386(3) 0.3193(3) 1.0690(2) 0.0488(7) Uani 1 1 d . . .
N3 N 0.8456(3) 0.1491(4) 0.8430(3) 0.0709(9) Uani 1 1 d . . .
O1 O 0.1131(2) -0.0661(2) 0.93255(18) 0.0535(7) Uani 1 1 d . . .
O2 O 0.6496(3) 0.3911(3) 0.9982(2) 0.0713(8) Uani 1 1 d . . .
O3 O 0.6605(3) 0.1836(3) 0.7148(2) 0.0850(10) Uani 1 1 d . . .
O4 O 0.3886(4) 0.2448(4) 0.6255(3) 0.1043(11) Uani 1 1 d . . .
H4 H 0.4652 0.2173 0.6477 0.157 Uiso 1 1 calc R . .
C1 C 0.2051(5) -0.3445(5) 0.5532(3) 0.0725(12) Uani 1 1 d . . .
C2 C 0.2358(4) -0.2023(5) 0.5601(3) 0.0683(11) Uani 1 1 d . . .
H2 H 0.2514 -0.1770 0.4951 0.082 Uiso 1 1 calc R . .
C3 C 0.2429(4) -0.0978(4) 0.6656(3) 0.0571(9) Uani 1 1 d . . .
H3 H 0.2655 -0.0009 0.6722 0.068 Uiso 1 1 calc R . .
C4 C 0.2164(3) -0.1364(3) 0.7627(3) 0.0471(8) Uani 1 1 d . . .
C5 C 0.1830(4) -0.2818(4) 0.7509(3) 0.0594(10) Uani 1 1 d . . .
H5 H 0.1631 -0.3089 0.8143 0.071 Uiso 1 1 calc R . .
C6 C 0.1791(5) -0.3870(4) 0.6455(4) 0.0741(12) Uani 1 1 d . . .
H6 H 0.1591 -0.4842 0.6380 0.089 Uiso 1 1 calc R . .
C7 C 0.2139(3) -0.0295(3) 0.8783(3) 0.0446(8) Uani 1 1 d . . .
C8 C 0.3220(3) 0.1034(3) 0.9262(3) 0.0417(8) Uani 1 1 d . . .
C9 C 0.3153(3) 0.2021(3) 1.0339(3) 0.0420(8) Uani 1 1 d . . .
C10 C 0.2239(4) 0.3138(4) 1.2131(3) 0.0646(10) Uani 1 1 d . . .
H10A H 0.1800 0.2730 1.2668 0.078 Uiso 1 1 calc R . .
H10B H 0.1660 0.3841 1.2004 0.078 Uiso 1 1 calc R . .
C11 C 0.3906(5) 0.3858(5) 1.2639(4) 0.0875(14) Uani 1 1 d . . .
H11A H 0.3971 0.4671 1.3336 0.105 Uiso 1 1 calc R . .
H11B H 0.4449 0.3181 1.2858 0.105 Uiso 1 1 calc R . .
C12 C 0.4666(4) 0.4376(4) 1.1784(3) 0.0623(10) Uani 1 1 d . . .
H12A H 0.4249 0.5173 1.1662 0.075 Uiso 1 1 calc R . .
H12B H 0.5767 0.4712 1.2085 0.075 Uiso 1 1 calc R . .
C13 C 0.5309(4) 0.3059(4) 0.9867(3) 0.0513(9) Uani 1 1 d . . .
C14 C 0.4590(3) 0.1687(3) 0.8844(3) 0.0452(8) Uani 1 1 d . . .
H14 H 0.4206 0.1952 0.8169 0.054 Uiso 1 1 calc R . .
C15 C 0.5803(4) 0.0779(4) 0.8537(3) 0.0526(9) Uani 1 1 d . . .
H15A H 0.6321 0.0665 0.9240 0.063 Uiso 1 1 calc R . .
H15B H 0.5290 -0.0173 0.8005 0.063 Uiso 1 1 calc R . .
C16 C 0.6991(4) 0.1441(4) 0.7985(3) 0.0584(10) Uani 1 1 d . . .
C17 C 0.9719(5) 0.2048(5) 0.7905(5) 0.0928(15) Uani 1 1 d . . .
H17A H 1.0532 0.1512 0.7934 0.111 Uiso 1 1 calc R . .
H17B H 0.9323 0.1909 0.7095 0.111 Uiso 1 1 calc R . .
C18 C 1.0326(7) 0.3529(6) 0.8515(7) 0.155(3) Uani 1 1 d . . .
H18A H 0.9531 0.4063 0.8456 0.232 Uiso 1 1 calc R . .
H18B H 1.1158 0.3864 0.8183 0.232 Uiso 1 1 calc R . .
H18C H 1.0701 0.3667 0.9319 0.232 Uiso 1 1 calc R . .
C19 C 0.1797(6) 0.1632(7) 0.4688(5) 0.128(2) Uani 1 1 d . . .
H19A H 0.1294 0.0924 0.4976 0.193 Uiso 1 1 calc R . .
H19B H 0.1525 0.1300 0.3853 0.193 Uiso 1 1 calc R . .
H19C H 0.1474 0.2524 0.4998 0.193 Uiso 1 1 calc R . .
C20 C 0.3459(6) 0.1856(7) 0.5048(4) 0.1052(17) Uani 1 1 d . . .
H20A H 0.3778 0.0942 0.4783 0.126 Uiso 1 1 calc R . .
H20B H 0.3972 0.2499 0.4696 0.126 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.368(4) . ?
N1 C9 1.320(4) . ?
N1 C10 1.473(4) . ?
N1 H1 0.8600 . ?
N2 C13 1.381(4) . ?
N2 C9 1.388(4) . ?
N2 C12 1.452(4) . ?
N3 C16 1.337(4) . ?
N3 C17 1.492(5) . ?
O1 C7 1.267(3) . ?
O2 C13 1.215(4) . ?
O3 C16 1.235(4) . ?
O4 C20 1.391(5) . ?
O4 H4 0.8200 . ?
C1 C6 1.362(6) . ?
C1 C2 1.374(6) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C7 1.499(4) . ?
C5 C6 1.387(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.416(4) . ?
C8 C9 1.403(4) . ?
C8 C14 1.524(4) . ?
C10 C11 1.507(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.501(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.522(4) . ?
C14 C15 1.533(4) . ?
C14 H14 0.9800 . ?
C15 C16 1.510(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.413(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.455(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C10 123.3(3) . . ?
C9 N1 H1 118.4 . . ?
C10 N1 H1 118.4 . . ?
C13 N2 C9 110.6(3) . . ?
C13 N2 C12 125.2(3) . . ?
C9 N2 C12 124.1(3) . . ?
C16 N3 C17 119.6(3) . . ?
C20 O4 H4 109.5 . . ?
C6 C1 F1 118.6(4) . . ?
C6 C1 C2 122.9(4) . . ?
F1 C1 C2 118.4(4) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C7 117.6(3) . . ?
C3 C4 C7 123.6(3) . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 118.4(4) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C8 121.7(3) . . ?
O1 C7 C4 116.5(3) . . ?
C8 C7 C4 121.7(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 C14 107.2(2) . . ?
C7 C8 C14 132.4(3) . . ?
N1 C9 N2 118.6(3) . . ?
N1 C9 C8 130.5(3) . . ?
N2 C9 C8 110.9(3) . . ?
N1 C10 C11 109.2(3) . . ?
N1 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
N1 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C10 111.4(4) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C11 108.8(3) . . ?
N2 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
N2 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O2 C13 N2 123.9(3) . . ?
O2 C13 C14 127.6(3) . . ?
N2 C13 C14 108.5(3) . . ?
C13 C14 C8 102.5(2) . . ?
C13 C14 C15 110.1(3) . . ?
C8 C14 C15 117.4(2) . . ?
C13 C14 H14 108.8 . . ?
C8 C14 H14 108.8 . . ?
C15 C14 H14 108.8 . . ?
C16 C15 C14 112.8(3) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
O3 C16 N3 123.6(3) . . ?
O3 C16 C15 121.2(3) . . ?
N3 C16 C15 115.1(3) . . ?
C18 C17 N3 110.4(5) . . ?
C18 C17 H17A 109.6 . . ?
N3 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
N3 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 C19 110.2(4) . . ?
O4 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
O4 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?

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
C6 C1 C2 C3 1.0(6) . . . . ?
F1 C1 C2 C3 179.8(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 C7 -176.7(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C7 C4 C5 C6 178.3(3) . . . . ?
F1 C1 C6 C5 -178.4(3) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
C4 C5 C6 C1 -1.5(6) . . . . ?
C5 C4 C7 O1 -35.9(4) . . . . ?
C3 C4 C7 O1 140.9(3) . . . . ?
C5 C4 C7 C8 142.1(3) . . . . ?
C3 C4 C7 C8 -41.1(5) . . . . ?
O1 C7 C8 C9 -3.0(5) . . . . ?
C4 C7 C8 C9 179.1(3) . . . . ?
O1 C7 C8 C14 175.4(3) . . . . ?
C4 C7 C8 C14 -2.4(5) . . . . ?
C10 N1 C9 N2 0.2(5) . . . . ?
C10 N1 C9 C8 -179.5(3) . . . . ?
C13 N2 C9 N1 -178.8(3) . . . . ?
C12 N2 C9 N1 2.2(5) . . . . ?
C13 N2 C9 C8 0.9(4) . . . . ?
C12 N2 C9 C8 -178.0(3) . . . . ?
C7 C8 C9 N1 -5.2(5) . . . . ?
C14 C8 C9 N1 176.1(3) . . . . ?
C7 C8 C9 N2 175.1(3) . . . . ?
C14 C8 C9 N2 -3.7(3) . . . . ?
C9 N1 C10 C11 -28.4(5) . . . . ?
N1 C10 C11 C12 54.0(5) . . . . ?
C13 N2 C12 C11 -154.8(4) . . . . ?
C9 N2 C12 C11 24.0(5) . . . . ?
C10 C11 C12 N2 -51.6(5) . . . . ?
C9 N2 C13 O2 -177.1(3) . . . . ?
C12 N2 C13 O2 1.9(5) . . . . ?
C9 N2 C13 C14 2.2(4) . . . . ?
C12 N2 C13 C14 -178.8(3) . . . . ?
O2 C13 C14 C8 175.1(3) . . . . ?
N2 C13 C14 C8 -4.2(3) . . . . ?
O2 C13 C14 C15 49.4(4) . . . . ?
N2 C13 C14 C15 -129.9(3) . . . . ?
C9 C8 C14 C13 4.6(3) . . . . ?
C7 C8 C14 C13 -173.9(3) . . . . ?
C9 C8 C14 C15 125.4(3) . . . . ?
C7 C8 C14 C15 -53.2(5) . . . . ?
C13 C14 C15 C16 -70.9(3) . . . . ?
C8 C14 C15 C16 172.4(3) . . . . ?
C17 N3 C16 O3 -0.1(6) . . . . ?
C17 N3 C16 C15 176.5(3) . . . . ?
C14 C15 C16 O3 -50.8(5) . . . . ?
C14 C15 C16 N3 132.5(3) . . . . ?
C16 N3 C17 C18 94.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 998644'
