# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_417b
_database_code_depnum_ccdc_archive 'CCDC 1810840'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 F3 N2 O, C4 H5 O6, H2 O'
_chemical_formula_sum            'C10 H17 F3 N2 O8'
_chemical_formula_weight         350.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0330 0.0200 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.7271(19)
_cell_length_b                   7.2173(14)
_cell_length_c                   11.150(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.74(3)
_cell_angle_gamma                90
_cell_volume                     727.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      32.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.356
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7283
_diffrn_reflns_av_unetI/netI     0.1622
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         38.403
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             2880
_reflns_number_gt                2071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.860
_reflns_Friedel_fraction_full    0.927

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 664 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1730(3) 0.1277(4) 0.5210(2) 0.0251(7) Uani 1 1 d . . . . .
F2 F 0.2903(3) -0.1227(4) 0.6090(2) 0.0284(8) Uani 1 1 d . . . . .
F3 F 0.0700(3) -0.0708(5) 0.6073(2) 0.0293(8) Uani 1 1 d . . . . .
O1 O 0.4271(3) -0.0967(6) 0.9066(3) 0.0259(9) Uani 1 1 d . . . . .
O2 O 0.7133(3) 1.1214(5) 0.9063(3) 0.0187(8) Uani 1 1 d . . . . .
O3 O 0.9105(3) 1.1118(5) 0.8464(3) 0.0182(8) Uani 1 1 d . . . . .
O4 O 0.6939(3) 0.7463(5) 0.9133(3) 0.0199(8) Uani 1 1 d . . . . .
H4 H 0.6199 0.8295 0.8994 0.030 Uiso 1 1 d R U . . .
O5 O 0.6667(3) 0.8143(5) 0.6471(3) 0.0248(9) Uani 1 1 d . . . . .
H5 H 0.6255 0.7228 0.5888 0.037 Uiso 1 1 d R U . . .
O6 O 0.6930(3) 0.4504(5) 0.6673(3) 0.0215(8) Uani 1 1 d . . . . .
O7 O 0.9095(3) 0.4607(5) 0.8379(2) 0.0177(8) Uani 1 1 d . . . . .
H7 H 0.8987 0.3351 0.8355 0.027 Uiso 1 1 d R U . . .
O8 O 0.5287(3) 0.1473(5) 0.5747(2) 0.0196(8) Uani 1 1 d . . . . .
H8A H 0.5712 0.0326 0.5977 0.029 Uiso 1 1 d R U . . .
H8B H 0.5996 0.2376 0.6080 0.029 Uiso 1 1 d R U . . .
N1 N 0.1902(4) -0.0863(6) 0.8952(3) 0.0184(9) Uani 1 1 d . . . . .
H1A H 0.0996 -0.0369 0.8561 0.022 Uiso 1 1 d R U . . .
H1B H 0.2059 -0.1713 0.9579 0.022 Uiso 1 1 d R U . . .
N2 N 0.4099(4) 0.1993(6) 0.7600(3) 0.0187(10) Uani 1 1 d . . . . .
H2A H 0.4845 0.1518 0.8278 0.022 Uiso 1 1 d R U . . .
H2B H 0.4275 0.1753 0.6877 0.022 Uiso 1 1 d R U . . .
C1 C 0.3010(4) -0.0339(7) 0.8608(4) 0.0182(12) Uani 1 1 d . . . . .
C2 C 0.2648(4) 0.1130(7) 0.7516(4) 0.0163(11) Uani 1 1 d . . . . .
C3 C 0.1669(4) 0.2782(7) 0.7575(4) 0.0202(11) Uani 1 1 d . . . . .
H3A H 0.0634 0.2588 0.6978 0.024 Uiso 1 1 calc R U . . .
H3B H 0.1683 0.2943 0.8461 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2337(4) 0.4462(8) 0.7170(4) 0.0209(12) Uani 1 1 d . . . . .
H4A H 0.1996 0.4552 0.6218 0.025 Uiso 1 1 calc R U . . .
H4B H 0.2077 0.5620 0.7512 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3985(5) 0.4094(8) 0.7763(5) 0.0259(13) Uani 1 1 d . . . . .
H5A H 0.4391 0.4448 0.8687 0.031 Uiso 1 1 calc R U . . .
H5B H 0.4520 0.4783 0.7303 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1997(5) 0.0104(8) 0.6215(4) 0.0194(11) Uani 1 1 d . . . . .
C7 C 0.8079(5) 1.0341(7) 0.8773(4) 0.0154(11) Uani 1 1 d . . . . .
C8 C 0.8076(4) 0.8241(7) 0.8768(4) 0.0154(11) Uani 1 1 d . . . . .
H8 H 0.9045 0.7829 0.9423 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7978(4) 0.7464(7) 0.7454(4) 0.0157(11) Uani 1 1 d . . . . .
H9 H 0.8860 0.7885 0.7270 0.019 Uiso 1 1 calc R U . . .
C10 C 0.7946(5) 0.5360(7) 0.7470(4) 0.0152(11) 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 C6 1.351(5) . ?
F2 C6 1.345(6) . ?
F3 C6 1.346(5) . ?
O1 C1 1.227(5) . ?
O2 C7 1.252(5) . ?
O3 C7 1.297(5) . ?
O4 C8 1.427(5) . ?
O4 H4 0.9060 . ?
O5 C9 1.426(5) . ?
O5 H5 0.9090 . ?
O6 C10 1.224(5) . ?
O7 C10 1.317(5) . ?
O7 H7 0.9120 . ?
O8 H8A 0.9180 . ?
O8 H8B 0.9210 . ?
N1 C1 1.326(6) . ?
N1 H1A 0.8999 . ?
N1 H1B 0.9000 . ?
N2 C2 1.514(6) . ?
N2 C5 1.536(7) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.8999 . ?
C1 C2 1.553(7) . ?
C2 C6 1.541(6) . ?
C2 C3 1.542(7) . ?
C3 C4 1.521(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.514(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.515(7) . ?
C8 C9 1.539(6) . ?
C8 H8 1.0000 . ?
C9 C10 1.519(7) . ?
C9 H9 1.0000 . ?

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
C8 O4 H4 109.9 . . ?
C9 O5 H5 109.4 . . ?
C10 O7 H7 109.4 . . ?
H8A O8 H8B 109.5 . . ?
C1 N1 H1A 120.2 . . ?
C1 N1 H1B 119.8 . . ?
H1A N1 H1B 120.0 . . ?
C2 N2 C5 107.9(4) . . ?
C2 N2 H2A 109.8 . . ?
C5 N2 H2A 110.3 . . ?
C2 N2 H2B 110.3 . . ?
C5 N2 H2B 110.0 . . ?
H2A N2 H2B 108.5 . . ?
O1 C1 N1 124.6(5) . . ?
O1 C1 C2 118.7(4) . . ?
N1 C1 C2 116.7(4) . . ?
N2 C2 C6 107.7(4) . . ?
N2 C2 C3 104.8(4) . . ?
C6 C2 C3 111.5(3) . . ?
N2 C2 C1 107.3(3) . . ?
C6 C2 C1 107.7(4) . . ?
C3 C2 C1 117.3(4) . . ?
C4 C3 C2 105.4(4) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C5 C4 C3 103.3(4) . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C4 C5 N2 103.4(4) . . ?
C4 C5 H5A 111.1 . . ?
N2 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
N2 C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
F2 C6 F3 107.4(4) . . ?
F2 C6 F1 107.1(4) . . ?
F3 C6 F1 106.9(3) . . ?
F2 C6 C2 112.6(3) . . ?
F3 C6 C2 111.1(4) . . ?
F1 C6 C2 111.5(4) . . ?
O2 C7 O3 124.2(5) . . ?
O2 C7 C8 120.2(4) . . ?
O3 C7 C8 115.6(4) . . ?
O4 C8 C7 113.2(4) . . ?
O4 C8 C9 110.3(3) . . ?
C7 C8 C9 111.5(4) . . ?
O4 C8 H8 107.2 . . ?
C7 C8 H8 107.2 . . ?
C9 C8 H8 107.2 . . ?
O5 C9 C10 109.6(3) . . ?
O5 C9 C8 109.2(4) . . ?
C10 C9 C8 110.4(4) . . ?
O5 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
C8 C9 H9 109.2 . . ?
O6 C10 O7 125.2(4) . . ?
O6 C10 C9 120.8(4) . . ?
O7 C10 C9 114.0(4) . . ?

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
C5 N2 C2 C6 121.2(4) . . . . ?
C5 N2 C2 C3 2.4(4) . . . . ?
C5 N2 C2 C1 -123.0(4) . . . . ?
O1 C1 C2 N2 -21.1(6) . . . . ?
N1 C1 C2 N2 160.7(4) . . . . ?
O1 C1 C2 C6 94.6(5) . . . . ?
N1 C1 C2 C6 -83.5(5) . . . . ?
O1 C1 C2 C3 -138.6(4) . . . . ?
N1 C1 C2 C3 43.2(6) . . . . ?
N2 C2 C3 C4 21.3(4) . . . . ?
C6 C2 C3 C4 -95.0(4) . . . . ?
C1 C2 C3 C4 140.1(4) . . . . ?
C2 C3 C4 C5 -37.1(5) . . . . ?
C3 C4 C5 N2 37.8(5) . . . . ?
C2 N2 C5 C4 -25.1(5) . . . . ?
N2 C2 C6 F2 59.3(5) . . . . ?
C3 C2 C6 F2 173.8(4) . . . . ?
C1 C2 C6 F2 -56.1(5) . . . . ?
N2 C2 C6 F3 179.8(4) . . . . ?
C3 C2 C6 F3 -65.7(5) . . . . ?
C1 C2 C6 F3 64.4(5) . . . . ?
N2 C2 C6 F1 -61.0(5) . . . . ?
C3 C2 C6 F1 53.5(5) . . . . ?
C1 C2 C6 F1 -176.4(3) . . . . ?
O2 C7 C8 O4 -0.8(5) . . . . ?
O3 C7 C8 O4 179.1(3) . . . . ?
O2 C7 C8 C9 124.3(4) . . . . ?
O3 C7 C8 C9 -55.8(5) . . . . ?
O4 C8 C9 O5 68.4(5) . . . . ?
C7 C8 C9 O5 -58.3(5) . . . . ?
O4 C8 C9 C10 -52.2(5) . . . . ?
C7 C8 C9 C10 -178.9(4) . . . . ?
O5 C9 C10 O6 3.3(6) . . . . ?
C8 C9 C10 O6 123.6(4) . . . . ?
O5 C9 C10 O7 -177.9(3) . . . . ?
C8 C9 C10 O7 -57.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O1 0.91 1.98 2.808(4) 151 1_565
O5 H5 O8 0.91 1.96 2.775(4) 148 2_656
O7 H7 O3 0.91 1.62 2.520(5) 170 1_545
O8 H8A O5 0.92 1.81 2.725(5) 176 1_545
O8 H8B O6 0.92 1.78 2.680(5) 164 .
N1 H1A O3 0.90 2.10 2.941(5) 156 1_445
N1 H1B O2 0.90 2.07 2.948(5) 167 2_637
N2 H2A O2 0.90 2.08 2.850(5) 143 1_545
N2 H2B O8 0.90 1.88 2.741(5) 161 .
C3 H3B O4 0.99 2.54 3.417(5) 148 2_647
C5 H5A O1 0.99 2.38 3.307(6) 156 2_657

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.082

