# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_21
_database_code_depnum_ccdc_archive 'CCDC 1978281'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_audit_creation_date             2018-08-08
_audit_creation_method           'by CrystalStructure 4.3'



_chemical_formula_sum            'C18 H18 F3 N O4'
_chemical_formula_moiety         'C18 H18 F3 N O4'
_chemical_formula_weight         369.34
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.18600(6)
_cell_length_b                   11.35580(7)
_cell_length_c                   15.52960(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1796.312(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16416
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      75.23
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768.00
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.980

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20749
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_theta_max         75.443
_diffrn_reflns_theta_min         5.835
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3627
_reflns_number_gt                3576
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.994

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.1016
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3627
_refine_ls_number_parameters     240
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0670P)²+0.0871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.049(3)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.22896(17) 0.75184(16) 0.44307(15) 0.1128(6) Uani 1 1 d . . . . .
F2 F -0.05845(18) 0.85656(14) 0.42218(15) 0.1120(6) Uani 1 1 d . . . . .
F3 F -0.0498(2) 0.70746(19) 0.50776(10) 0.1138(6) Uani 1 1 d . . . . .
O8 O -0.11736(14) 0.71749(13) 0.28252(11) 0.0735(4) Uani 1 1 d D . . . .
O10 O 0.1922(2) 0.4774(3) 0.47219(12) 0.1157(8) Uani 1 1 d . . . . .
O11 O 0.31310(17) 0.38077(16) 0.37621(13) 0.0879(5) Uani 1 1 d . . . . .
O15 O 0.68073(14) 0.60698(16) 0.19544(11) 0.0787(4) Uani 1 1 d . . . . .
N4 N -0.01891(16) 0.45159(14) 0.35211(11) 0.0638(4) Uani 1 1 d . . . . .
C1 C -0.2197(2) 0.4956(2) 0.39517(18) 0.0795(6) Uani 1 1 d . . . . .
H1 H -0.2943 0.5371 0.4115 0.095 Uiso 1 1 calc R U . . .
C2 C -0.2078(3) 0.3725(2) 0.3898(2) 0.0882(7) Uani 1 1 d . . . . .
H2 H -0.2731 0.3177 0.4020 0.106 Uiso 1 1 calc R U . . .
C3 C -0.0846(2) 0.34835(19) 0.36380(18) 0.0796(6) Uani 1 1 d . . . . .
H3 H -0.0500 0.2735 0.3552 0.096 Uiso 1 1 calc R U . . .
C5 C 0.11740(19) 0.46106(16) 0.32538(11) 0.0601(4) Uani 1 1 d . . . . .
H5 H 0.1346 0.4009 0.2816 0.072 Uiso 1 1 calc R U . . .
C6 C 0.14096(17) 0.58321(15) 0.28508(11) 0.0553(4) Uani 1 1 d . . . . .
H6 H 0.0879 0.5874 0.2325 0.066 Uiso 1 1 calc R U . . .
C7 C 0.09065(17) 0.67838(16) 0.34596(12) 0.0597(4) Uani 1 1 d . . . . .
H7A H 0.1122 0.7554 0.3229 0.072 Uiso 1 1 calc R U . . .
H7B H 0.1335 0.6704 0.4014 0.072 Uiso 1 1 calc R U . . .
C8 C -0.05816(19) 0.66843(16) 0.35755(12) 0.0612(4) Uani 1 1 d . . . . .
C9 C -0.10086(19) 0.54345(17) 0.37198(12) 0.0623(4) Uani 1 1 d . . . . .
C10 C 0.2092(2) 0.4398(2) 0.40136(14) 0.0716(5) Uani 1 1 d . . . . .
C11 C 0.4156(3) 0.3657(4) 0.4397(3) 0.1230(13) Uani 1 1 d . . . . .
H11A H 0.4867 0.3216 0.4150 0.148 Uiso 1 1 calc R U . . .
H11B H 0.4470 0.4415 0.4577 0.148 Uiso 1 1 calc R U . . .
H11C H 0.3813 0.3240 0.4885 0.148 Uiso 1 1 calc R U . . .
C12 C 0.28337(18) 0.59691(15) 0.25850(10) 0.0553(4) Uani 1 1 d . . . . .
C13 C 0.3286(2) 0.5387(2) 0.18604(12) 0.0705(5) Uani 1 1 d . . . . .
H13 H 0.2692 0.4974 0.1520 0.085 Uiso 1 1 calc R U . . .
C14 C 0.4598(2) 0.5403(2) 0.16287(13) 0.0726(5) Uani 1 1 d . . . . .
H14 H 0.4879 0.5001 0.1141 0.087 Uiso 1 1 calc R U . . .
C15 C 0.54832(19) 0.60165(17) 0.21239(12) 0.0630(4) Uani 1 1 d . . . . .
C16 C 0.5044(2) 0.6653(2) 0.28269(15) 0.0716(5) Uani 1 1 d . . . . .
H16 H 0.5631 0.7102 0.3147 0.086 Uiso 1 1 calc R U . . .
C17 C 0.3735(2) 0.66195(19) 0.30531(13) 0.0650(4) Uani 1 1 d . . . . .
H17 H 0.3452 0.7043 0.3531 0.078 Uiso 1 1 calc R U . . .
C18 C 0.7334(3) 0.5265(4) 0.1369(3) 0.1401(18) Uani 1 1 d . . . . .
H18A H 0.8260 0.5400 0.1312 0.168 Uiso 1 1 calc R U . . .
H18B H 0.7186 0.4478 0.1575 0.168 Uiso 1 1 calc R U . . .
H18C H 0.6918 0.5362 0.0820 0.168 Uiso 1 1 calc R U . . .
C19 C -0.0995(3) 0.7457(2) 0.43301(19) 0.0834(6) Uani 1 1 d . . . . .
H8O H -0.200(2) 0.675(3) 0.274(3) 0.125(12) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C19 1.330(3) . ?
F2 C19 1.337(3) . ?
F3 C19 1.339(4) . ?
O8 C8 1.425(2) . ?
O8 H8O 0.977(7) . ?
O10 C10 1.193(3) . ?
O11 C10 1.312(3) . ?
O11 C11 1.447(4) . ?
O15 C15 1.375(2) . ?
O15 C18 1.396(4) . ?
N4 C3 1.362(3) . ?
N4 C9 1.371(2) . ?
N4 C5 1.453(2) . ?
C1 C9 1.375(3) . ?
C1 C2 1.405(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 C10 1.525(3) . ?
C5 C6 1.541(2) . ?
C5 H5 0.9800 . ?
C6 C12 1.516(2) . ?
C6 C7 1.525(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.501(3) . ?
C8 C19 1.523(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.384(3) . ?
C12 C17 1.385(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 O8 H8O 107(2) . . ?
C10 O11 C11 116.1(3) . . ?
C15 O15 C18 118.2(2) . . ?
C3 N4 C9 109.02(16) . . ?
C3 N4 C5 124.81(17) . . ?
C9 N4 C5 126.14(16) . . ?
C9 C1 C2 107.6(2) . . ?
C9 C1 H1 126.2 . . ?
C2 C1 H1 126.2 . . ?
C3 C2 C1 107.5(2) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 N4 108.8(2) . . ?
C2 C3 H3 125.6 . . ?
N4 C3 H3 125.6 . . ?
N4 C5 C10 110.70(16) . . ?
N4 C5 C6 109.35(15) . . ?
C10 C5 C6 111.17(16) . . ?
N4 C5 H5 108.5 . . ?
C10 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C12 C6 C7 114.68(14) . . ?
C12 C6 C5 110.61(15) . . ?
C7 C6 C5 109.51(14) . . ?
C12 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
C5 C6 H6 107.2 . . ?
C6 C7 C8 110.70(14) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O8 C8 C9 111.66(16) . . ?
O8 C8 C19 106.66(17) . . ?
C9 C8 C19 110.48(17) . . ?
O8 C8 C7 107.09(15) . . ?
C9 C8 C7 111.98(15) . . ?
C19 C8 C7 108.75(17) . . ?
N4 C9 C1 107.10(18) . . ?
N4 C9 C8 120.62(17) . . ?
C1 C9 C8 131.91(19) . . ?
O10 C10 O11 125.1(2) . . ?
O10 C10 C5 124.6(2) . . ?
O11 C10 C5 110.19(19) . . ?
O11 C11 H11A 109.5 . . ?
O11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O11 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.44(17) . . ?
C13 C12 C6 119.39(16) . . ?
C17 C12 C6 123.12(15) . . ?
C12 C13 C14 121.77(18) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 119.65(18) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 O15 123.96(18) . . ?
C14 C15 C16 119.60(19) . . ?
O15 C15 C16 116.42(17) . . ?
C17 C16 C15 119.94(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 121.47(18) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O15 C18 H18A 109.5 . . ?
O15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 C19 F2 106.0(2) . . ?
F1 C19 F3 106.9(2) . . ?
F2 C19 F3 107.2(2) . . ?
F1 C19 C8 113.2(2) . . ?
F2 C19 C8 111.1(2) . . ?
F3 C19 C8 112.05(19) . . ?

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
C9 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 N4 -0.4(3) . . . . ?
C9 N4 C3 C2 0.8(3) . . . . ?
C5 N4 C3 C2 179.0(2) . . . . ?
C3 N4 C5 C10 -79.5(3) . . . . ?
C9 N4 C5 C10 98.4(2) . . . . ?
C3 N4 C5 C6 157.7(2) . . . . ?
C9 N4 C5 C6 -24.4(2) . . . . ?
N4 C5 C6 C12 178.60(14) . . . . ?
C10 C5 C6 C12 56.07(18) . . . . ?
N4 C5 C6 C7 51.26(18) . . . . ?
C10 C5 C6 C7 -71.27(19) . . . . ?
C12 C6 C7 C8 170.98(14) . . . . ?
C5 C6 C7 C8 -64.00(19) . . . . ?
C6 C7 C8 O8 -77.63(18) . . . . ?
C6 C7 C8 C9 45.1(2) . . . . ?
C6 C7 C8 C19 167.46(17) . . . . ?
C3 N4 C9 C1 -0.8(2) . . . . ?
C5 N4 C9 C1 -179.06(19) . . . . ?
C3 N4 C9 C8 -174.6(2) . . . . ?
C5 N4 C9 C8 7.1(3) . . . . ?
C2 C1 C9 N4 0.6(3) . . . . ?
C2 C1 C9 C8 173.4(2) . . . . ?
O8 C8 C9 N4 103.2(2) . . . . ?
C19 C8 C9 N4 -138.2(2) . . . . ?
C7 C8 C9 N4 -16.9(3) . . . . ?
O8 C8 C9 C1 -68.8(3) . . . . ?
C19 C8 C9 C1 49.7(3) . . . . ?
C7 C8 C9 C1 171.1(2) . . . . ?
C11 O11 C10 O10 -2.7(4) . . . . ?
C11 O11 C10 C5 173.4(2) . . . . ?
N4 C5 C10 O10 -41.5(3) . . . . ?
C6 C5 C10 O10 80.3(3) . . . . ?
N4 C5 C10 O11 142.39(18) . . . . ?
C6 C5 C10 O11 -95.9(2) . . . . ?
C7 C6 C12 C13 -161.25(18) . . . . ?
C5 C6 C12 C13 74.3(2) . . . . ?
C7 C6 C12 C17 21.3(2) . . . . ?
C5 C6 C12 C17 -103.1(2) . . . . ?
C17 C12 C13 C14 2.9(3) . . . . ?
C6 C12 C13 C14 -174.6(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 O15 178.9(2) . . . . ?
C13 C14 C15 C16 -2.8(4) . . . . ?
C18 O15 C15 C14 -14.6(4) . . . . ?
C18 O15 C15 C16 167.1(3) . . . . ?
C14 C15 C16 C17 3.3(4) . . . . ?
O15 C15 C16 C17 -178.3(2) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C13 C12 C17 C16 -2.4(3) . . . . ?
C6 C12 C17 C16 175.1(2) . . . . ?
O8 C8 C19 F1 58.7(3) . . . . ?
C9 C8 C19 F1 -62.8(3) . . . . ?
C7 C8 C19 F1 173.9(2) . . . . ?
O8 C8 C19 F2 -60.4(3) . . . . ?
C9 C8 C19 F2 178.1(2) . . . . ?
C7 C8 C19 F2 54.8(3) . . . . ?
O8 C8 C19 F3 179.7(2) . . . . ?
C9 C8 C19 F3 58.2(3) . . . . ?
C7 C8 C19 F3 -65.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O8 H8O O15 . . 1_455 2.763(2) 0.98(3) 1.89(3) 148(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


