# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I
_audit_block_doi                 10.5517/cc1jk83g
_database_code_depnum_ccdc_archive 'CCDC 1416765'
_audit_update_record             
;
2015-08-04 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 F3 N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         423.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   14.1742(13)
_cell_length_b                   11.9882(11)
_cell_length_c                   11.3206(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.796(3)
_cell_angle_gamma                90
_cell_volume                     1923.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9751
_cell_measurement_theta_min      2.8494
_cell_measurement_theta_max      25.0501
_cell_measurement_temperature    93.0(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.0(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            12346
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3328
_reflns_number_gt                3073
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1279
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²+1.2577P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v3.0.29'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruke AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.15832(12) 1.24585(14) 0.21020(16) 0.0211(4) Uani d . . . 1 . .
H H1A 0.0972 1.2239 0.1761 0.032 Uiso calc U . R 1 . .
H H1B 0.1712 1.324 0.1906 0.032 Uiso calc U . R 1 . .
H H1C 0.1569 1.2371 0.2962 0.032 Uiso calc U . R 1 . .
C C2 0.33027(12) 1.19856(14) 0.21745(16) 0.0206(4) Uani d . . . 1 . .
H H2A 0.3256 1.1909 0.3034 0.031 Uiso calc U . R 1 . .
H H2B 0.3485 1.2752 0.1979 0.031 Uiso calc U . R 1 . .
H H2C 0.378 1.1466 0.1882 0.031 Uiso calc U . R 1 . .
C C3 0.23965(13) 1.17686(14) 0.02653(15) 0.0213(4) Uani d . . . 1 . .
H H3A 0.2883 1.1254 -0.0012 0.032 Uiso calc U . R 1 . .
H H3B 0.2551 1.2529 0.0016 0.032 Uiso calc U . R 1 . .
H H3C 0.1783 1.1553 -0.0073 0.032 Uiso calc U . R 1 . .
C C4 0.23548(12) 1.17219(13) 0.16002(15) 0.0170(4) Uani d . . . 1 . .
C C5 0.13964(11) 1.00385(13) 0.17380(14) 0.0143(4) Uani d . . . 1 . .
C C6 0.09675(11) 0.80264(13) 0.18621(14) 0.0142(4) Uani d . . . 1 . .
C C7 0.03855(11) 0.78986(14) 0.08677(15) 0.0163(4) Uani d . . . 1 . .
H H7 0.0196 0.8516 0.0395 0.02 Uiso calc U . R 1 . .
C C8 0.01000(12) 0.68225(14) 0.06093(15) 0.0187(4) Uani d . . . 1 . .
H H8 -0.03 0.6699 -0.0059 0.022 Uiso calc U . R 1 . .
C C9 0.03806(12) 0.59038(14) 0.13011(15) 0.0189(4) Uani d . . . 1 . .
H H9 0.0163 0.5179 0.1094 0.023 Uiso calc U . R 1 . .
C C10 0.09649(11) 0.60335(13) 0.22716(15) 0.0168(4) Uani d . . . 1 . .
H H10 0.1156 0.541 0.2735 0.02 Uiso calc U . R 1 . .
C C11 0.12684(11) 0.71114(13) 0.25553(14) 0.0146(3) Uani d . . . 1 . .
C C12 0.18709(11) 0.75572(13) 0.34705(14) 0.0141(3) Uani d . . . 1 . .
C C13 0.23419(11) 0.69954(13) 0.44496(14) 0.0146(4) Uani d . . . 1 . .
C C14 0.29258(11) 0.77306(13) 0.52746(14) 0.0152(4) Uani d . . . 1 . .
C C15 0.29284(11) 0.88549(14) 0.51436(14) 0.0160(4) Uani d . . . 1 . .
C C16 0.22821(11) 0.94243(13) 0.42836(14) 0.0155(4) Uani d . . . 1 . .
C C17 0.19121(11) 0.86910(13) 0.33311(14) 0.0141(3) Uani d . . . 1 . .
C C18 0.40275(12) 0.63133(14) 0.59924(15) 0.0194(4) Uani d . . . 1 . .
H H18 0.3664 0.5638 0.5737 0.023 Uiso calc U . R 1 . .
C C19 0.47262(14) 0.66244(17) 0.50567(19) 0.0317(5) Uani d . . . 1 . .
H H19A 0.4391 0.6751 0.4305 0.048 Uiso calc U . R 1 . .
H H19B 0.5182 0.6018 0.4963 0.048 Uiso calc U . R 1 . .
H H19C 0.5059 0.7307 0.5293 0.048 Uiso calc U . R 1 . .
C C20 0.44770(14) 0.61101(17) 0.71833(17) 0.0288(4) Uani d . . . 1 . .
H H20A 0.4807 0.6786 0.7446 0.043 Uiso calc U . R 1 . .
H H20B 0.4928 0.5494 0.7127 0.043 Uiso calc U . R 1 . .
H H20C 0.3988 0.5918 0.7753 0.043 Uiso calc U . R 1 . .
C C21 0.35247(12) 0.96006(14) 0.59236(15) 0.0193(4) Uani d . . . 1 . .
F F1 0.43224(8) 0.91174(9) 0.62951(12) 0.0393(3) Uani d . . . 1 . .
F F2 0.30714(9) 0.99459(11) 0.68782(10) 0.0400(3) Uani d . . . 1 . .
F F3 0.37996(8) 1.05163(9) 0.53530(10) 0.0317(3) Uani d . . . 1 . .
N N1 0.13729(9) 0.90009(11) 0.23554(12) 0.0137(3) Uani d . . . 1 . .
O O1 0.07651(8) 1.03218(9) 0.10939(10) 0.0184(3) Uani d . . . 1 . .
O O2 0.22039(8) 1.05451(9) 0.19845(10) 0.0154(3) Uani d . . . 1 . .
O O3 0.20435(9) 1.03899(9) 0.44139(10) 0.0194(3) Uani d . . . 1 . .
O O4 0.22932(8) 0.59927(9) 0.46243(11) 0.0198(3) Uani d . . . 1 . .
O O5 0.33734(8) 0.72504(9) 0.61940(10) 0.0175(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C4 . 1.522(2) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C4 . 1.518(2) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 C4 . 1.514(2) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 O2 . 1.4925(18) ?
C5 O1 . 1.196(2) ?
C5 O2 . 1.322(2) ?
C5 N1 . 1.427(2) ?
C6 C7 . 1.395(2) ?
C6 C11 . 1.411(2) ?
C6 N1 . 1.413(2) ?
C7 C8 . 1.382(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.406(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.375(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.398(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.437(2) ?
C12 C17 . 1.370(2) ?
C12 C13 . 1.452(2) ?
C13 O4 . 1.220(2) ?
C13 C14 . 1.521(2) ?
C14 O5 . 1.341(2) ?
C14 C15 . 1.356(2) ?
C15 C16 . 1.493(2) ?
C15 C21 . 1.507(2) ?
C16 O3 . 1.216(2) ?
C16 C17 . 1.481(2) ?
C17 N1 . 1.385(2) ?
C18 O5 . 1.476(2) ?
C18 C20 . 1.503(3) ?
C18 C19 . 1.507(3) ?
C18 H18 . 1.0 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 F2 . 1.331(2) ?
C21 F1 . 1.333(2) ?
C21 F3 . 1.335(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 C1 H1A . . 109.5 ?
C4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C2 H2A . . 109.5 ?
C4 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C4 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O2 C4 C3 . . 109.49(13) ?
O2 C4 C2 . . 101.63(13) ?
C3 C4 C2 . . 111.91(14) ?
O2 C4 C1 . . 109.45(13) ?
C3 C4 C1 . . 112.92(14) ?
C2 C4 C1 . . 110.83(14) ?
O1 C5 O2 . . 129.54(15) ?
O1 C5 N1 . . 121.59(14) ?
O2 C5 N1 . . 108.84(13) ?
C7 C6 C11 . . 122.29(15) ?
C7 C6 N1 . . 129.97(15) ?
C11 C6 N1 . . 107.74(14) ?
C8 C7 C6 . . 116.20(15) ?
C8 C7 H7 . . 121.9 ?
C6 C7 H7 . . 121.9 ?
C7 C8 C9 . . 122.25(16) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
C10 C9 C8 . . 121.27(15) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C9 C10 C11 . . 117.90(15) ?
C9 C10 H10 . . 121.0 ?
C11 C10 H10 . . 121.0 ?
C10 C11 C6 . . 120.07(16) ?
C10 C11 C12 . . 133.44(16) ?
C6 C11 C12 . . 106.49(14) ?
C17 C12 C11 . . 108.18(14) ?
C17 C12 C13 . . 121.91(14) ?
C11 C12 C13 . . 129.83(15) ?
O4 C13 C12 . . 123.66(15) ?
O4 C13 C14 . . 120.20(15) ?
C12 C13 C14 . . 116.14(14) ?
O5 C14 C15 . . 120.64(15) ?
O5 C14 C13 . . 118.38(14) ?
C15 C14 C13 . . 120.75(14) ?
C14 C15 C16 . . 121.55(15) ?
C14 C15 C21 . . 121.85(15) ?
C16 C15 C21 . . 116.42(14) ?
O3 C16 C17 . . 123.86(15) ?
O3 C16 C15 . . 121.71(15) ?
C17 C16 C15 . . 114.28(14) ?
C12 C17 N1 . . 109.52(14) ?
C12 C17 C16 . . 121.35(14) ?
N1 C17 C16 . . 127.37(14) ?
O5 C18 C20 . . 104.12(13) ?
O5 C18 C19 . . 109.91(14) ?
C20 C18 C19 . . 113.33(16) ?
O5 C18 H18 . . 109.8 ?
C20 C18 H18 . . 109.8 ?
C19 C18 H18 . . 109.8 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
F2 C21 F1 . . 107.20(15) ?
F2 C21 F3 . . 106.53(14) ?
F1 C21 F3 . . 104.95(14) ?
F2 C21 C15 . . 112.77(14) ?
F1 C21 C15 . . 113.16(14) ?
F3 C21 C15 . . 111.68(14) ?
C17 N1 C6 . . 108.07(13) ?
C17 N1 C5 . . 127.43(13) ?
C6 N1 C5 . . 122.61(14) ?
C5 O2 C4 . . 119.99(12) ?
C14 O5 C18 . . 119.87(12) ?



