# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_kor2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (R)-2,3,3,3-Tetrafluoro-N-methyl-N-((R)-1-phenylethyl)propanamide  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 F4 N O'
_chemical_formula_weight         263.23

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.07446(13)
_cell_length_b                   8.98778(19)
_cell_length_c                   24.2410(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1323.46(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    1.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Kuma
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21223
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         5.25
_diffrn_reflns_theta_max         75.62
_reflns_number_total             2734
_reflns_number_gt                2492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0772P)²+0.1076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         2734
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1019(2) 0.71762(16) 0.79717(6) 0.0783(4) Uani 1 1 d . . .
F1 F 0.1626(3) 0.8916(2) 0.71388(7) 0.1228(7) Uani 1 1 d . . .
F2 F -0.3799(3) 0.7741(2) 0.69868(8) 0.1323(7) Uani 1 1 d . . .
F3 F -0.0936(5) 0.64769(19) 0.68475(8) 0.1460(9) Uani 1 1 d . . .
F4 F -0.1457(5) 0.8446(2) 0.63797(7) 0.1492(9) Uani 1 1 d . . .
N1 N -0.2170(3) 0.83070(16) 0.82115(7) 0.0666(4) Uani 1 1 d . . .
C1 C -0.0511(3) 0.80177(18) 0.78689(8) 0.0611(4) Uani 1 1 d . . .
C2 C -0.0519(4) 0.8775(2) 0.73023(9) 0.0721(5) Uani 1 1 d . . .
H2A H -0.1216 0.9756 0.7327 0.087 Uiso 1 1 calc R . .
C3 C -0.1661(6) 0.7840(3) 0.68730(10) 0.0936(7) Uani 1 1 d . . .
C4 C -0.2270(4) 0.7479(2) 0.87407(9) 0.0743(5) Uani 1 1 d . . .
H4A H -0.0938 0.6866 0.8760 0.089 Uiso 1 1 calc R . .
C5 C -0.4215(6) 0.6420(3) 0.87366(14) 0.1097(9) Uani 1 1 d . . .
H5A H -0.4096 0.5761 0.8426 0.165 Uiso 1 1 calc R . .
H5B H -0.5557 0.6980 0.8709 0.165 Uiso 1 1 calc R . .
H5C H -0.4224 0.5850 0.9071 0.165 Uiso 1 1 calc R . .
C6 C -0.2166(4) 0.8568(3) 0.92208(8) 0.0781(5) Uani 1 1 d . . .
C7 C -0.0325(6) 0.9463(3) 0.92717(11) 0.0983(8) Uani 1 1 d . . .
H7A H 0.0814 0.9373 0.9017 0.118 Uiso 1 1 calc R . .
C8 C -0.0148(9) 1.0495(4) 0.96961(14) 0.1280(13) Uani 1 1 d . . .
H8A H 0.1096 1.1093 0.9725 0.154 Uiso 1 1 calc R . .
C9 C -0.1819(11) 1.0620(4) 1.00695(14) 0.1391(16) Uani 1 1 d . . .
H9A H -0.1734 1.1327 1.0349 0.167 Uiso 1 1 calc R . .
C10 C -0.3623(9) 0.9709(5) 1.00339(14) 0.1372(14) Uani 1 1 d . . .
H10A H -0.4732 0.9779 1.0297 0.165 Uiso 1 1 calc R . .
C11 C -0.3809(6) 0.8678(4) 0.96078(12) 0.1096(9) Uani 1 1 d . . .
H11A H -0.5041 0.8066 0.9585 0.132 Uiso 1 1 calc R . .
C12 C -0.3945(4) 0.9373(3) 0.81078(10) 0.0858(6) Uani 1 1 d . . .
H12A H -0.3710 0.9847 0.7758 0.129 Uiso 1 1 calc R . .
H12B H -0.3957 1.0110 0.8394 0.129 Uiso 1 1 calc R . .
H12C H -0.5330 0.8859 0.8103 0.129 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0708(8) 0.0740(8) 0.0902(9) 0.0046(7) -0.0012(7) 0.0166(7)
F1 0.0859(9) 0.1665(17) 0.1162(11) 0.0390(12) 0.0189(9) -0.0096(10)
F2 0.1109(13) 0.1423(15) 0.1437(15) -0.0351(13) -0.0373(11) -0.0159(12)
F3 0.230(3) 0.0935(10) 0.1142(12) -0.0388(9) -0.0474(15) 0.0510(14)
F4 0.220(2) 0.1558(16) 0.0722(9) 0.0101(9) -0.0206(12) 0.0196(18)
N1 0.0678(9) 0.0630(8) 0.0691(8) 0.0047(7) -0.0012(7) 0.0109(7)
C1 0.0609(8) 0.0492(7) 0.0731(10) -0.0018(7) -0.0047(8) -0.0011(7)
C2 0.0765(11) 0.0654(10) 0.0743(11) 0.0050(9) 0.0017(9) -0.0005(9)
C3 0.126(2) 0.0810(14) 0.0736(12) -0.0043(11) -0.0133(14) 0.0208(14)
C4 0.0762(11) 0.0677(10) 0.0789(11) 0.0125(9) 0.0031(9) 0.0087(9)
C5 0.122(2) 0.0966(17) 0.1100(19) 0.0109(15) 0.0107(17) -0.0279(17)
C6 0.0891(14) 0.0779(11) 0.0673(11) 0.0124(9) 0.0015(10) 0.0101(12)
C7 0.119(2) 0.0955(16) 0.0804(14) 0.0066(13) -0.0018(14) -0.0077(17)
C8 0.190(4) 0.1010(19) 0.093(2) 0.0046(16) -0.023(2) -0.018(2)
C9 0.233(5) 0.105(2) 0.0797(18) -0.0039(16) -0.014(3) 0.037(3)
C10 0.167(4) 0.164(4) 0.0814(18) -0.009(2) 0.019(2) 0.041(3)
C11 0.112(2) 0.130(2) 0.0871(16) 0.0093(16) 0.0189(15) 0.015(2)
C12 0.0785(13) 0.0895(13) 0.0895(14) 0.0051(12) -0.0053(11) 0.0276(11)

_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 C1 1.224(2) . ?
F1 C2 1.368(3) . ?
F2 C3 1.331(4) . ?
F3 C3 1.303(3) . ?
F4 C3 1.320(3) . ?
N1 C1 1.331(3) . ?
N1 C12 1.464(2) . ?
N1 C4 1.484(3) . ?
C1 C2 1.533(3) . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9800 . ?
C4 C5 1.517(4) . ?
C4 C6 1.522(3) . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.373(4) . ?
C6 C7 1.383(4) . ?
C7 C8 1.389(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.365(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.371(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.392(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C1 N1 C12 125.32(17) . . ?
C1 N1 C4 118.17(15) . . ?
C12 N1 C4 116.51(16) . . ?
O1 C1 N1 124.66(17) . . ?
O1 C1 C2 117.32(18) . . ?
N1 C1 C2 118.02(15) . . ?
F1 C2 C3 106.9(2) . . ?
F1 C2 C1 107.32(17) . . ?
C3 C2 C1 111.88(17) . . ?
F1 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
F3 C3 F4 108.3(2) . . ?
F3 C3 F2 106.1(3) . . ?
F4 C3 F2 107.9(3) . . ?
F3 C3 C2 113.7(2) . . ?
F4 C3 C2 110.6(2) . . ?
F2 C3 C2 110.1(2) . . ?
N1 C4 C5 109.90(19) . . ?
N1 C4 C6 109.70(16) . . ?
C5 C4 C6 116.1(2) . . ?
N1 C4 H4A 106.9 . . ?
C5 C4 H4A 106.9 . . ?
C6 C4 H4A 106.9 . . ?
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 . . ?
C11 C6 C7 119.0(3) . . ?
C11 C6 C4 122.6(3) . . ?
C7 C6 C4 118.4(2) . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C6 C11 C10 119.7(4) . . ?
C6 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C12 N1 C1 O1 176.3(2) . . . . ?
C4 N1 C1 O1 -4.4(3) . . . . ?
C12 N1 C1 C2 -4.4(3) . . . . ?
C4 N1 C1 C2 174.88(16) . . . . ?
O1 C1 C2 F1 -28.7(2) . . . . ?
N1 C1 C2 F1 151.94(19) . . . . ?
O1 C1 C2 C3 88.2(2) . . . . ?
N1 C1 C2 C3 -91.1(2) . . . . ?
F1 C2 C3 F3 65.4(3) . . . . ?
C1 C2 C3 F3 -51.8(3) . . . . ?
F1 C2 C3 F4 -56.7(3) . . . . ?
C1 C2 C3 F4 -173.8(2) . . . . ?
F1 C2 C3 F2 -175.8(2) . . . . ?
C1 C2 C3 F2 67.0(3) . . . . ?
C1 N1 C4 C5 -111.4(2) . . . . ?
C12 N1 C4 C5 67.9(3) . . . . ?
C1 N1 C4 C6 119.78(19) . . . . ?
C12 N1 C4 C6 -60.9(2) . . . . ?
N1 C4 C6 C11 120.5(2) . . . . ?
C5 C4 C6 C11 -4.8(3) . . . . ?
N1 C4 C6 C7 -60.5(3) . . . . ?
C5 C4 C6 C7 174.1(2) . . . . ?
C11 C6 C7 C8 -2.0(4) . . . . ?
C4 C6 C7 C8 179.0(2) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C8 C9 C10 C11 -2.1(6) . . . . ?
C7 C6 C11 C10 1.7(4) . . . . ?
C4 C6 C11 C10 -179.3(3) . . . . ?
C9 C10 C11 C6 0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        75.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 989111'
