# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_160103a
_audit_block_doi                 10.5517/cc1kl6kx
_database_code_depnum_ccdc_archive 'CCDC 1447469'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(R,Z)-3-(4-fluorophenyl)-2-(hydroxyimino)-3-(trifluoromethyl)-3,5,6,7-tetrahydrobenzofuran-4(2H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F4 N O3'
_chemical_formula_weight         329.25

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.7967(4)
_cell_length_b                   9.2428(4)
_cell_length_c                   17.2636(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1403.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3309
_cell_measurement_theta_min      5.1130
_cell_measurement_theta_max      71.0200

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_T_max  0.6880
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8522
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.12
_diffrn_reflns_theta_max         66.45
_reflns_number_total             2477
_reflns_number_gt                2166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0355P)²+0.3309P] 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       0.0143(6)
_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)
_chemical_absolute_configuration R
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.0196(2) 0.3849(2) 0.92412(11) 0.0806(6) Uani 1 1 d . . .
F2 F 0.08690(19) 0.25168(18) 0.56177(10) 0.0610(5) Uani 1 1 d . . .
F3 F 0.1163(2) 0.47932(19) 0.56547(12) 0.0724(6) Uani 1 1 d . . .
F4 F 0.2749(2) 0.3468(2) 0.50360(9) 0.0706(6) Uani 1 1 d . . .
N1 N 0.3115(2) 0.0742(2) 0.63873(14) 0.0486(6) Uani 1 1 d . . .
O1 O 0.53001(19) 0.21663(17) 0.64337(12) 0.0482(5) Uani 1 1 d . . .
O2 O 0.3317(2) 0.67821(18) 0.62728(13) 0.0571(6) Uani 1 1 d . . .
O3 O 0.4191(2) -0.03696(19) 0.64167(17) 0.0689(7) Uani 1 1 d . . .
H3 H 0.3759 -0.1153 0.6382 0.103 Uiso 1 1 calc R . .
C1 C 0.3739(3) 0.1958(3) 0.64029(15) 0.0365(5) Uani 1 1 d . . .
C2 C 0.2913(3) 0.3432(2) 0.63991(13) 0.0319(5) Uani 1 1 d . . .
C3 C 0.4302(3) 0.4414(2) 0.63236(14) 0.0336(5) Uani 1 1 d . . .
C4 C 0.4417(3) 0.5986(2) 0.62403(15) 0.0390(5) Uani 1 1 d . . .
C5 C 0.6001(3) 0.6574(3) 0.61418(19) 0.0504(7) Uani 1 1 d . . .
H5A H 0.6336 0.6957 0.6636 0.061 Uiso 1 1 calc R . .
H5B H 0.5960 0.7376 0.5780 0.061 Uiso 1 1 calc R . .
C6 C 0.7180(3) 0.5509(3) 0.58576(19) 0.0574(8) Uani 1 1 d . . .
H6A H 0.6987 0.5286 0.5317 0.069 Uiso 1 1 calc R . .
H6B H 0.8180 0.5946 0.5893 0.069 Uiso 1 1 calc R . .
C7 C 0.7157(3) 0.4125(3) 0.63248(19) 0.0513(7) Uani 1 1 d . . .
H7A H 0.7794 0.3400 0.6081 0.062 Uiso 1 1 calc R . .
H7B H 0.7537 0.4302 0.6844 0.062 Uiso 1 1 calc R . .
C8 C 0.5554(3) 0.3616(2) 0.63570(15) 0.0388(5) Uani 1 1 d . . .
C9 C 0.2004(3) 0.3620(2) 0.71501(13) 0.0340(5) Uani 1 1 d . . .
C10 C 0.0805(3) 0.2690(3) 0.73192(16) 0.0466(6) Uani 1 1 d . . .
H10 H 0.0513 0.1998 0.6958 0.056 Uiso 1 1 calc R . .
C11 C 0.0040(3) 0.2781(4) 0.80192(18) 0.0568(8) Uani 1 1 d . . .
H11 H -0.0773 0.2170 0.8128 0.068 Uiso 1 1 calc R . .
C12 C 0.0508(3) 0.3789(3) 0.85444(16) 0.0522(7) Uani 1 1 d . . .
C13 C 0.1673(3) 0.4720(3) 0.83996(16) 0.0513(7) Uani 1 1 d . . .
H13 H 0.1961 0.5404 0.8766 0.062 Uiso 1 1 calc R . .
C14 C 0.2418(3) 0.4628(3) 0.76965(14) 0.0412(6) Uani 1 1 d . . .
H14 H 0.3215 0.5259 0.7591 0.049 Uiso 1 1 calc R . .
C15 C 0.1907(3) 0.3559(3) 0.56753(15) 0.0414(6) 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 C12 1.354(3) . ?
F2 C15 1.331(3) . ?
F3 C15 1.316(3) . ?
F4 C15 1.332(3) . ?
N1 C1 1.251(3) . ?
N1 O3 1.398(3) . ?
O1 C8 1.365(3) . ?
O1 C1 1.388(3) . ?
O2 C4 1.217(3) . ?
O3 H3 0.8200 . ?
C1 C2 1.544(3) . ?
C2 C3 1.527(3) . ?
C2 C9 1.533(3) . ?
C2 C15 1.536(3) . ?
C3 C8 1.327(3) . ?
C3 C4 1.463(3) . ?
C4 C5 1.506(3) . ?
C5 C6 1.512(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.512(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.487(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C14 1.375(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(4) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 O3 111.3(2) . . ?
C8 O1 C1 107.13(19) . . ?
N1 O3 H3 109.5 . . ?
N1 C1 O1 124.0(2) . . ?
N1 C1 C2 125.9(2) . . ?
O1 C1 C2 110.09(19) . . ?
C3 C2 C9 114.98(19) . . ?
C3 C2 C15 110.26(19) . . ?
C9 C2 C15 112.25(19) . . ?
C3 C2 C1 98.53(18) . . ?
C9 C2 C1 109.96(19) . . ?
C15 C2 C1 109.99(19) . . ?
C8 C3 C4 119.9(2) . . ?
C8 C3 C2 109.25(18) . . ?
C4 C3 C2 130.8(2) . . ?
O2 C4 C3 122.8(2) . . ?
O2 C4 C5 121.5(2) . . ?
C3 C4 C5 115.7(2) . . ?
C4 C5 C6 115.9(2) . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 111.6(2) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 107.5(2) . . ?
C8 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C3 C8 O1 114.5(2) . . ?
C3 C8 C7 127.5(2) . . ?
O1 C8 C7 118.0(2) . . ?
C14 C9 C10 118.4(2) . . ?
C14 C9 C2 121.2(2) . . ?
C10 C9 C2 120.2(2) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
F1 C12 C13 118.8(3) . . ?
F1 C12 C11 118.7(3) . . ?
C13 C12 C11 122.5(3) . . ?
C12 C13 C14 118.7(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C13 121.2(3) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
F3 C15 F2 106.5(2) . . ?
F3 C15 F4 108.0(2) . . ?
F2 C15 F4 105.9(2) . . ?
F3 C15 C2 112.0(2) . . ?
F2 C15 C2 113.6(2) . . ?
F4 C15 C2 110.4(2) . . ?

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
O3 N1 C1 O1 0.9(4) . . . . ?
O3 N1 C1 C2 -178.5(3) . . . . ?
C8 O1 C1 N1 173.5(3) . . . . ?
C8 O1 C1 C2 -7.0(3) . . . . ?
N1 C1 C2 C3 -173.4(3) . . . . ?
O1 C1 C2 C3 7.2(3) . . . . ?
N1 C1 C2 C9 66.0(3) . . . . ?
O1 C1 C2 C9 -113.4(2) . . . . ?
N1 C1 C2 C15 -58.1(3) . . . . ?
O1 C1 C2 C15 122.4(2) . . . . ?
C9 C2 C3 C8 112.0(2) . . . . ?
C15 C2 C3 C8 -119.9(2) . . . . ?
C1 C2 C3 C8 -4.8(2) . . . . ?
C9 C2 C3 C4 -66.9(3) . . . . ?
C15 C2 C3 C4 61.2(3) . . . . ?
C1 C2 C3 C4 176.3(3) . . . . ?
C8 C3 C4 O2 -173.6(3) . . . . ?
C2 C3 C4 O2 5.2(4) . . . . ?
C8 C3 C4 C5 4.1(4) . . . . ?
C2 C3 C4 C5 -177.1(2) . . . . ?
O2 C4 C5 C6 -161.2(3) . . . . ?
C3 C4 C5 C6 21.1(4) . . . . ?
C4 C5 C6 C7 -49.9(4) . . . . ?
C5 C6 C7 C8 50.3(3) . . . . ?
C4 C3 C8 O1 -179.9(2) . . . . ?
C2 C3 C8 O1 1.1(3) . . . . ?
C4 C3 C8 C7 0.5(4) . . . . ?
C2 C3 C8 C7 -178.6(3) . . . . ?
C1 O1 C8 C3 3.8(3) . . . . ?
C1 O1 C8 C7 -176.5(2) . . . . ?
C6 C7 C8 C3 -28.4(4) . . . . ?
C6 C7 C8 O1 151.9(2) . . . . ?
C3 C2 C9 C14 1.3(3) . . . . ?
C15 C2 C9 C14 -125.8(2) . . . . ?
C1 C2 C9 C14 111.4(2) . . . . ?
C3 C2 C9 C10 -173.7(2) . . . . ?
C15 C2 C9 C10 59.2(3) . . . . ?
C1 C2 C9 C10 -63.6(3) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C2 C9 C10 C11 175.5(2) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C10 C11 C12 F1 -177.5(3) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
F1 C12 C13 C14 178.1(2) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C2 C9 C14 C13 -174.8(2) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C3 C2 C15 F3 -73.3(3) . . . . ?
C9 C2 C15 F3 56.3(3) . . . . ?
C1 C2 C15 F3 179.0(2) . . . . ?
C3 C2 C15 F2 165.90(19) . . . . ?
C9 C2 C15 F2 -64.5(3) . . . . ?
C1 C2 C15 F2 58.3(3) . . . . ?
C3 C2 C15 F4 47.1(3) . . . . ?
C9 C2 C15 F4 176.7(2) . . . . ?
C1 C2 C15 F4 -60.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.45
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
