# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_test1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 F N2 O2'
_chemical_formula_weight         224.23

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'
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   'P 21 21 21'

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                   8.1246(3)
_cell_length_b                   9.2109(3)
_cell_length_c                   14.8139(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1108.59(6)
_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       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7300
_exptl_absorpt_correction_T_max  0.8571
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2419
_diffrn_reflns_av_R_equivalents  0.0077
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.66
_diffrn_reflns_theta_max         67.00
_reflns_number_total             1629
_reflns_number_gt                1520
_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)+(0.0760P)²+0.3328P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_number_reflns         1629
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.8706(4) 0.3254(3) -0.18792(18) 0.0546(7) Uani 1 1 d . . .
C2 C 0.8792(4) 0.1804(3) -0.17059(17) 0.0532(7) Uani 1 1 d . . .
H2 H 0.9003 0.1150 -0.2170 0.064 Uiso 1 1 calc R . .
C3 C 0.8559(3) 0.1307(3) -0.08237(16) 0.0454(6) Uani 1 1 d . . .
C4 C 0.8270(3) 0.2320(3) -0.01271(16) 0.0430(6) Uani 1 1 d . . .
C5 C 0.8191(4) 0.3772(3) -0.03549(19) 0.0555(7) Uani 1 1 d . . .
H5 H 0.7984 0.4445 0.0099 0.067 Uiso 1 1 calc R . .
C6 C 0.8405(4) 0.4271(3) -0.1228(2) 0.0603(7) Uani 1 1 d . . .
H6 H 0.8347 0.5255 -0.1365 0.072 Uiso 1 1 calc R . .
C8 C 0.7756(4) -0.0686(3) 0.01657(18) 0.0589(7) Uani 1 1 d . . .
H8 H 0.6570 -0.0528 0.0095 0.071 Uiso 1 1 calc R . .
C9 C 0.8347(4) 0.0186(3) 0.09416(18) 0.0618(8) Uani 1 1 d . . .
H9A H 0.9523 0.0042 0.1009 0.074 Uiso 1 1 calc R . .
H9B H 0.7818 -0.0161 0.1488 0.074 Uiso 1 1 calc R . .
C10 C 0.8003(3) 0.1803(3) 0.08380(16) 0.0444(6) Uani 1 1 d . . .
H10 H 0.6852 0.1982 0.1001 0.053 Uiso 1 1 calc R . .
C11 C 0.9101(4) 0.2668(4) 0.14801(18) 0.0646(8) Uani 1 1 d . . .
H11A H 1.0246 0.2538 0.1315 0.077 Uiso 1 1 calc R . .
H11B H 0.8840 0.3693 0.1436 0.077 Uiso 1 1 calc R . .
C12 C 0.8071(6) -0.2305(3) 0.0262(2) 0.0791(11) Uani 1 1 d . . .
H12A H 0.9235 -0.2477 0.0300 0.119 Uiso 1 1 calc R . .
H12B H 0.7631 -0.2805 -0.0252 0.119 Uiso 1 1 calc R . .
H12C H 0.7547 -0.2655 0.0801 0.119 Uiso 1 1 calc R . .
F1 F 0.8926(3) 0.3716(2) -0.27434(10) 0.0784(6) Uani 1 1 d . . .
N1 N 0.8830(4) 0.2155(4) 0.24254(17) 0.0706(8) Uani 1 1 d . . .
N2 N 0.8592(4) -0.0157(2) -0.06388(14) 0.0602(7) Uani 1 1 d . . .
H2A H 0.9097 -0.0748 -0.0992 0.072 Uiso 1 1 calc R . .
O1 O 0.9905(5) 0.1463(6) 0.27876(19) 0.1464(19) Uani 1 1 d . . .
O2 O 0.7519(4) 0.2367(3) 0.27633(16) 0.0920(9) Uani 1 1 d . . .

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
C1 0.0519(15) 0.0672(17) 0.0446(12) 0.0119(12) -0.0028(12) -0.0087(14)
C2 0.0589(16) 0.0602(16) 0.0404(12) -0.0057(12) 0.0000(12) -0.0032(14)
C3 0.0455(13) 0.0490(13) 0.0416(11) -0.0022(11) 0.0017(11) -0.0004(11)
C4 0.0417(13) 0.0467(13) 0.0407(12) -0.0033(11) -0.0014(10) -0.0011(10)
C5 0.0671(18) 0.0470(14) 0.0522(13) -0.0055(12) 0.0007(14) 0.0017(14)
C6 0.0691(19) 0.0484(14) 0.0635(16) 0.0090(14) -0.0037(15) -0.0037(14)
C8 0.0755(18) 0.0461(14) 0.0551(15) 0.0004(12) 0.0068(14) -0.0019(14)
C9 0.083(2) 0.0583(16) 0.0440(13) 0.0008(12) 0.0065(14) 0.0043(15)
C10 0.0445(13) 0.0496(13) 0.0391(12) -0.0060(10) 0.0041(11) 0.0001(11)
C11 0.073(2) 0.0769(19) 0.0439(14) -0.0067(13) 0.0018(14) -0.0206(17)
C12 0.122(3) 0.0467(15) 0.0692(18) 0.0034(15) 0.003(2) 0.0037(18)
F1 0.0963(14) 0.0893(12) 0.0494(9) 0.0220(9) 0.0017(9) -0.0136(12)
N1 0.0739(17) 0.095(2) 0.0430(12) -0.0082(13) -0.0039(14) -0.0157(16)
N2 0.0945(19) 0.0443(11) 0.0418(10) -0.0071(9) 0.0128(12) 0.0039(12)
O1 0.100(2) 0.267(6) 0.0721(18) 0.037(3) -0.0219(17) 0.017(3)
O2 0.112(2) 0.103(2) 0.0615(14) 0.0021(13) 0.0285(14) 0.0168(18)

_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
C1 F1 1.361(3) . ?
C1 C2 1.362(4) . ?
C1 C6 1.367(4) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.376(3) . ?
C3 C4 1.411(3) . ?
C4 C5 1.381(4) . ?
C4 C10 1.522(3) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 N2 1.455(4) . ?
C8 C9 1.482(4) . ?
C8 C12 1.520(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.523(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.528(4) . ?
C10 H10 0.9800 . ?
C11 N1 1.494(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 O2 1.193(4) . ?
N1 O1 1.207(5) . ?
N2 H2A 0.8600 . ?

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
F1 C1 C2 118.5(3) . . ?
F1 C1 C6 118.3(3) . . ?
C2 C1 C6 123.2(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N2 C3 C2 120.3(2) . . ?
N2 C3 C4 120.4(2) . . ?
C2 C3 C4 119.3(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 C10 121.7(2) . . ?
C3 C4 C10 120.3(2) . . ?
C4 C5 C6 123.0(3) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C5 117.0(3) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
N2 C8 C9 107.6(2) . . ?
N2 C8 C12 109.1(3) . . ?
C9 C8 C12 113.8(3) . . ?
N2 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C12 C8 H8 108.7 . . ?
C8 C9 C10 113.1(2) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C4 C10 C9 112.0(2) . . ?
C4 C10 C11 109.8(2) . . ?
C9 C10 C11 109.9(2) . . ?
C4 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
N1 C11 C10 109.4(2) . . ?
N1 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N1 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 N1 O1 123.1(3) . . ?
O2 N1 C11 118.2(3) . . ?
O1 N1 C11 118.5(3) . . ?
C3 N2 C8 118.8(2) . . ?
C3 N2 H2A 120.6 . . ?
C8 N2 H2A 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 955384'
