# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cu_d8v18496_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21by0c
_database_code_depnum_ccdc_archive 'CCDC 1887342'
_audit_update_record             
;
2018-12-26 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H20 F3 N O5'
_chemical_formula_weight         303.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.6250(2)
_cell_length_b                   9.3524(3)
_cell_length_c                   13.0235(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.524(2)
_cell_angle_gamma                90
_cell_volume                     787.73(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5002
_cell_measurement_theta_min      11.747
_cell_measurement_theta_max      139.60

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4791
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10507
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.873
_diffrn_reflns_theta_max         66.494
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2741
_reflns_number_gt                2416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.956

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0621P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 987 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.21(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_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 0.4709(7) 0.8683(4) 0.8318(3) 0.1283(13) Uani 1 1 d . . . . .
F2 F 0.2305(6) 0.7205(6) 0.8372(3) 0.1345(15) Uani 1 1 d . . . . .
F3 F 0.5407(8) 0.6740(6) 0.9175(3) 0.1559(18) Uani 1 1 d . . . . .
O1 O 0.0486(4) 0.4559(3) 0.5067(2) 0.0719(8) Uani 1 1 d . . . . .
O2 O 0.3658(4) 0.3915(3) 0.5863(3) 0.0866(10) Uani 1 1 d . . . . .
H2 H 0.3117 0.3125 0.5847 0.130 Uiso 1 1 calc R U . . .
O3 O 0.3169(4) 0.5691(3) 0.3279(2) 0.0707(8) Uani 1 1 d . . . . .
O4 O 0.0973(4) 0.7566(3) 0.2773(2) 0.0680(7) Uani 1 1 d . . . . .
N1 N 0.2083(4) 0.7113(3) 0.4463(2) 0.0569(7) Uani 1 1 d . . . . .
C1 C 0.3212(5) 0.6314(4) 0.5346(3) 0.0536(8) Uani 1 1 d . . . . .
H1A H 0.4643 0.6206 0.5269 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2295(5) 0.4843(4) 0.5398(3) 0.0574(8) Uani 1 1 d . . . . .
C3 C 0.3220(6) 0.7164(4) 0.6352(3) 0.0645(9) Uani 1 1 d . . . . .
H3A H 0.3601 0.8146 0.6245 0.077 Uiso 1 1 calc R U . . .
H3B H 0.1830 0.7172 0.6478 0.077 Uiso 1 1 calc R U . . .
C4 C 0.4684(7) 0.6580(5) 0.7322(3) 0.0727(10) Uani 1 1 d . . . . .
H4 H 0.4404 0.5555 0.7367 0.087 Uiso 1 1 calc R U . . .
C5 C 0.6947(8) 0.6751(8) 0.7270(5) 0.112(2) Uani 1 1 d . . . . .
H5A H 0.7279 0.6083 0.6772 0.169 Uiso 1 1 calc R U . . .
H5B H 0.7808 0.6571 0.7951 0.169 Uiso 1 1 calc R U . . .
H5C H 0.7180 0.7707 0.7054 0.169 Uiso 1 1 calc R U . . .
C6 C 0.4256(9) 0.7289(7) 0.8298(4) 0.0957(15) Uani 1 1 d . . . . .
C7 C 0.2151(5) 0.6700(4) 0.3472(3) 0.0573(8) Uani 1 1 d . . . . .
C8 C 0.0629(7) 0.7299(6) 0.1635(3) 0.0785(11) Uani 1 1 d . . . . .
C9 C -0.0898(11) 0.8454(7) 0.1193(4) 0.1073(18) Uani 1 1 d . . . . .
H9A H -0.2102 0.8365 0.1486 0.161 Uiso 1 1 calc R U . . .
H9B H -0.1289 0.8359 0.0442 0.161 Uiso 1 1 calc R U . . .
H9C H -0.0276 0.9374 0.1369 0.161 Uiso 1 1 calc R U . . .
C10 C -0.0312(12) 0.5844(7) 0.1381(5) 0.115(2) Uani 1 1 d . . . . .
H10A H 0.0723 0.5124 0.1605 0.172 Uiso 1 1 calc R U . . .
H10B H -0.0839 0.5766 0.0637 0.172 Uiso 1 1 calc R U . . .
H10C H -0.1420 0.5712 0.1740 0.172 Uiso 1 1 calc R U . . .
C11 C 0.2665(11) 0.7494(11) 0.1289(5) 0.128(2) Uani 1 1 d . . . . .
H11A H 0.3328 0.8354 0.1593 0.192 Uiso 1 1 calc R U . . .
H11B H 0.2402 0.7559 0.0536 0.192 Uiso 1 1 calc R U . . .
H11C H 0.3549 0.6690 0.1520 0.192 Uiso 1 1 calc R U . . .
O5 O 0.2676(5) 0.1319(3) 0.6087(3) 0.0907(11) Uani 1 1 d G . . . .
H5D H 0.3791 0.0856 0.6302 0.136 Uiso 1 1 d G U . . .
H5E H 0.1725 0.0748 0.5795 0.136 Uiso 1 1 d G U . . .
H1 H 0.117(8) 0.788(6) 0.453(4) 0.079(13) 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 C6 1.337(8) . ?
F2 C6 1.319(7) . ?
F3 C6 1.332(7) . ?
O1 C2 1.212(4) . ?
O2 C2 1.303(4) . ?
O2 H2 0.8200 . ?
O3 C7 1.217(4) . ?
O4 C7 1.336(4) . ?
O4 C8 1.471(5) . ?
N1 C7 1.357(5) . ?
N1 C1 1.439(4) . ?
N1 H1 0.95(5) . ?
C1 C2 1.511(5) . ?
C1 C3 1.531(5) . ?
C1 H1A 0.9800 . ?
C3 C4 1.518(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.514(7) . ?
C4 C5 1.524(7) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C8 C10 1.504(8) . ?
C8 C9 1.506(8) . ?
C8 C11 1.523(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O5 H5D 0.8500 . ?
O5 H5E 0.8501 . ?

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
C2 O2 H2 109.5 . . ?
C7 O4 C8 121.6(3) . . ?
C7 N1 C1 119.6(3) . . ?
C7 N1 H1 117(3) . . ?
C1 N1 H1 123(3) . . ?
N1 C1 C2 111.4(3) . . ?
N1 C1 C3 108.6(3) . . ?
C2 C1 C3 111.2(3) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
C3 C1 H1A 108.5 . . ?
O1 C2 O2 123.5(3) . . ?
O1 C2 C1 124.1(3) . . ?
O2 C2 C1 112.5(3) . . ?
C4 C3 C1 114.1(3) . . ?
C4 C3 H3A 108.7 . . ?
C1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C6 C4 C3 109.8(4) . . ?
C6 C4 C5 110.9(4) . . ?
C3 C4 C5 112.5(4) . . ?
C6 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
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 . . ?
F2 C6 F3 107.6(5) . . ?
F2 C6 F1 106.0(6) . . ?
F3 C6 F1 105.9(5) . . ?
F2 C6 C4 113.6(4) . . ?
F3 C6 C4 112.0(5) . . ?
F1 C6 C4 111.2(5) . . ?
O3 C7 O4 126.7(3) . . ?
O3 C7 N1 123.5(3) . . ?
O4 C7 N1 109.8(3) . . ?
O4 C8 C10 109.9(4) . . ?
O4 C8 C9 102.0(4) . . ?
C10 C8 C9 110.7(4) . . ?
O4 C8 C11 108.9(4) . . ?
C10 C8 C11 113.2(6) . . ?
C9 C8 C11 111.5(6) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H5D O5 H5E 109.5 . . ?

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
C7 N1 C1 C2 -68.2(4) . . . . ?
C7 N1 C1 C3 169.0(3) . . . . ?
N1 C1 C2 O1 -28.6(5) . . . . ?
C3 C1 C2 O1 92.6(4) . . . . ?
N1 C1 C2 O2 152.9(3) . . . . ?
C3 C1 C2 O2 -85.8(4) . . . . ?
N1 C1 C3 C4 -169.3(3) . . . . ?
C2 C1 C3 C4 67.8(4) . . . . ?
C1 C3 C4 C6 -168.2(4) . . . . ?
C1 C3 C4 C5 67.8(5) . . . . ?
C3 C4 C6 F2 53.5(6) . . . . ?
C5 C4 C6 F2 178.4(6) . . . . ?
C3 C4 C6 F3 175.7(5) . . . . ?
C5 C4 C6 F3 -59.4(6) . . . . ?
C3 C4 C6 F1 -66.0(5) . . . . ?
C5 C4 C6 F1 58.9(6) . . . . ?
C8 O4 C7 O3 5.6(5) . . . . ?
C8 O4 C7 N1 -175.1(3) . . . . ?
C1 N1 C7 O3 -1.8(5) . . . . ?
C1 N1 C7 O4 178.9(3) . . . . ?
C7 O4 C8 C10 58.0(5) . . . . ?
C7 O4 C8 C9 175.5(4) . . . . ?
C7 O4 C8 C11 -66.6(6) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4



