# Electronic Supplementary Material (ESI) for Green 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_P027_002M
_database_code_depnum_ccdc_archive 'CCDC 1864239'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 F3 N O3'
_chemical_formula_weight         381.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.3180(17)
_cell_length_b                   11.515(2)
_cell_length_c                   11.539(2)
_cell_angle_alpha                61.60(3)
_cell_angle_beta                 78.05(3)
_cell_angle_gamma                75.08(3)
_cell_volume                     934.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14988
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8930
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.986
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4586
_reflns_number_gt                3876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'PAL BL2D-SMDC Program'
_computing_cell_refinement       HKL3000sm
_computing_data_reduction        HKL3000sm
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1208P)²+0.1221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1927
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
O1 O 0.04892(13) 0.21892(10) 0.37190(10) 0.0345(2) Uani 1 1 d . . . . .
O3 O -0.62493(13) 0.38370(10) 0.11427(10) 0.0383(3) Uani 1 1 d . . . . .
N1 N 0.36134(16) 0.09656(12) 0.83765(12) 0.0381(3) Uani 1 1 d . . . . .
F1 F 0.61750(13) 0.28949(11) 0.79198(10) 0.0511(3) Uani 1 1 d . . . . .
F2 F 0.86221(13) 0.22815(11) 0.71278(11) 0.0522(3) Uani 1 1 d . . . . .
C1 C 0.33465(17) 0.22124(14) 0.73911(13) 0.0333(3) Uani 1 1 d . . . . .
C14 C -0.16826(17) 0.21266(13) 0.27204(13) 0.0315(3) Uani 1 1 d . . . . .
C17 C -0.47400(17) 0.32241(13) 0.16378(13) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.07378(14) 0.04156(11) 0.33339(12) 0.0434(3) Uani 1 1 d . . . . .
C12 C 0.20709(18) 0.15515(14) 0.42932(14) 0.0341(3) Uani 1 1 d . . . . .
H12A H 0.297465 0.148846 0.360517 0.041 Uiso 1 1 calc R U . . .
H12B H 0.200275 0.063145 0.499906 0.041 Uiso 1 1 calc R U . . .
C19 C -0.25611(18) 0.33806(13) 0.26185(13) 0.0333(3) Uani 1 1 d . . . . .
H19 H -0.211185 0.385972 0.291679 0.040 Uiso 1 1 calc R U . . .
C13 C -0.00487(18) 0.14784(14) 0.32778(13) 0.0328(3) Uani 1 1 d . . . . .
C7 C 0.45385(18) 0.24811(13) 0.61343(14) 0.0335(3) Uani 1 1 d . . . . .
H7 H 0.437177 0.347051 0.554641 0.040 Uiso 1 1 calc R U . . .
C2 C 0.20114(18) 0.31978(13) 0.74708(14) 0.0350(3) Uani 1 1 d . . . . .
H2 H 0.186856 0.407221 0.675015 0.042 Uiso 1 1 calc R U . . .
C8 C 0.63712(18) 0.19657(14) 0.64351(14) 0.0356(3) Uani 1 1 d . . . . .
H8A H 0.648317 0.103443 0.715248 0.043 Uiso 1 1 calc R U . . .
H8B H 0.706836 0.193946 0.563778 0.043 Uiso 1 1 calc R U . . .
C15 C -0.23616(17) 0.14416(13) 0.22767(13) 0.0319(3) Uani 1 1 d . . . . .
H15 H -0.177428 0.058896 0.234753 0.038 Uiso 1 1 calc R U . . .
C3 C 0.08874(18) 0.29054(15) 0.86017(15) 0.0371(3) Uani 1 1 d . . . . .
C10 C 0.41476(18) 0.17743(14) 0.54058(13) 0.0338(3) Uani 1 1 d . . . . .
H10A H 0.502591 0.183540 0.466495 0.041 Uiso 1 1 calc R U . . .
H10B H 0.417668 0.081127 0.602387 0.041 Uiso 1 1 calc R U . . .
C18 C -0.40802(18) 0.39242(13) 0.20854(14) 0.0343(3) Uani 1 1 d . . . . .
H18 H -0.467484 0.477205 0.202332 0.041 Uiso 1 1 calc R U . . .
C11 C 0.24458(19) 0.23818(14) 0.48628(14) 0.0368(3) Uani 1 1 d . . . . .
H11A H 0.156917 0.240455 0.558121 0.044 Uiso 1 1 calc R U . . .
H11B H 0.244787 0.331507 0.416573 0.044 Uiso 1 1 calc R U . . .
C16 C -0.38820(18) 0.19790(13) 0.17317(13) 0.0328(3) Uani 1 1 d . . . . .
H16 H -0.432781 0.150262 0.142809 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2533(2) 0.06885(15) 0.94719(15) 0.0418(4) Uani 1 1 d . . . . .
H5 H 0.271293 -0.018955 1.018382 0.050 Uiso 1 1 calc R U . . .
C20 C -0.6937(2) 0.31862(16) 0.06245(15) 0.0399(3) Uani 1 1 d . . . . .
H20A H -0.617352 0.309885 -0.011197 0.060 Uiso 1 1 calc R U . . .
H20B H -0.801982 0.372040 0.030781 0.060 Uiso 1 1 calc R U . . .
H20C H -0.709008 0.229223 0.132151 0.060 Uiso 1 1 calc R U . . .
F3 F 0.70243(17) 0.40624(10) 0.58955(12) 0.0654(3) Uani 1 1 d . . . . .
C4 C 0.1168(2) 0.16148(16) 0.96223(15) 0.0409(3) Uani 1 1 d . . . . .
H4 H 0.043393 0.136645 1.041603 0.049 Uiso 1 1 calc R U . . .
C9 C 0.70306(19) 0.27974(15) 0.68398(16) 0.0393(3) Uani 1 1 d . . . . .
C6 C -0.0594(2) 0.39455(17) 0.87054(17) 0.0453(4) Uani 1 1 d . . . . .
H6A H -0.029127 0.483782 0.821964 0.068 Uiso 1 1 calc R U . . .
H6B H -0.091867 0.374483 0.963835 0.068 Uiso 1 1 calc R U . . .
H6C H -0.153283 0.392840 0.832547 0.068 Uiso 1 1 calc R U . . .


_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
O1 C13 1.3447(17) . ?
O1 C12 1.4526(17) . ?
O3 C17 1.3631(17) . ?
O3 C20 1.4265(18) . ?
N1 C1 1.338(2) . ?
N1 C5 1.342(2) . ?
F1 C9 1.3405(18) . ?
F2 C9 1.3436(18) . ?
C1 C2 1.3919(18) . ?
C1 C7 1.5224(19) . ?
C14 C15 1.3917(19) . ?
C14 C19 1.4013(18) . ?
C14 C13 1.484(2) . ?
C17 C16 1.3907(18) . ?
C17 C18 1.400(2) . ?
O2 C13 1.2083(17) . ?
C12 C11 1.5098(19) . ?
C19 C18 1.384(2) . ?
C7 C8 1.534(2) . ?
C7 C10 1.5410(18) . ?
C2 C3 1.389(2) . ?
C8 C9 1.496(2) . ?
C15 C16 1.391(2) . ?
C3 C4 1.386(2) . ?
C3 C6 1.511(2) . ?
C10 C11 1.525(2) . ?
C5 C4 1.389(2) . ?
F3 C9 1.3409(19) . ?

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
C13 O1 C12 114.10(10) . . ?
C17 O3 C20 117.41(11) . . ?
C1 N1 C5 117.20(12) . . ?
N1 C1 C2 122.55(13) . . ?
N1 C1 C7 116.14(12) . . ?
C2 C1 C7 121.24(13) . . ?
C15 C14 C19 118.95(13) . . ?
C15 C14 C13 117.54(11) . . ?
C19 C14 C13 123.52(13) . . ?
O3 C17 C16 124.12(13) . . ?
O3 C17 C18 115.49(11) . . ?
C16 C17 C18 120.38(13) . . ?
O1 C12 C11 108.67(11) . . ?
C18 C19 C14 120.30(13) . . ?
O2 C13 O1 122.59(13) . . ?
O2 C13 C14 123.85(13) . . ?
O1 C13 C14 113.56(11) . . ?
C1 C7 C8 111.82(11) . . ?
C1 C7 C10 109.26(12) . . ?
C8 C7 C10 108.75(11) . . ?
C3 C2 C1 120.15(13) . . ?
C9 C8 C7 114.05(11) . . ?
C16 C15 C14 121.38(12) . . ?
C4 C3 C2 117.23(13) . . ?
C4 C3 C6 121.43(14) . . ?
C2 C3 C6 121.34(14) . . ?
C11 C10 C7 112.70(11) . . ?
C19 C18 C17 119.97(12) . . ?
C12 C11 C10 109.70(11) . . ?
C15 C16 C17 119.02(13) . . ?
N1 C5 C4 123.60(14) . . ?
C3 C4 C5 119.27(14) . . ?
F1 C9 F3 105.92(13) . . ?
F1 C9 F2 105.76(12) . . ?
F3 C9 F2 106.05(14) . . ?
F1 C9 C8 113.66(13) . . ?
F3 C9 C8 113.21(13) . . ?
F2 C9 C8 111.61(12) . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.073

