# 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.
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#  fide research purposes only. It may contain copyright material
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data_tc317

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 F N O'
_chemical_formula_weight         193.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   6.0469(2)
_cell_length_b                   9.1864(3)
_cell_length_c                   9.4011(3)
_cell_angle_alpha                110.410(2)
_cell_angle_beta                 96.980(2)
_cell_angle_gamma                92.353(2)
_cell_volume                     483.85(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6489
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini Ultra'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14096
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1907
_reflns_number_gt                1711
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    Mecurry
_computing_publication_material  WinGX

_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)+(0.0378P)²+0.1864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1907
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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
C1 C 0.9519(2) 0.69884(14) 0.67740(14) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.9134(2) 0.83934(15) 0.81542(15) 0.0252(3) Uani 1 1 d . . . . .
H2 H 0.9550 0.8167 0.9114 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6782(2) 0.88681(16) 0.80997(15) 0.0289(3) Uani 1 1 d . . . . .
H3A H 0.6759 0.9931 0.8858 0.035 Uiso 1 1 calc R U . . .
H3B H 0.5806 0.8145 0.8374 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5895(2) 0.88407(15) 0.65064(15) 0.0267(3) Uani 1 1 d . . . . .
H4A H 0.6887 0.9541 0.6215 0.032 Uiso 1 1 calc R U . . .
H4B H 0.4380 0.9211 0.6498 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5803(2) 0.71805(14) 0.53693(14) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.4674 0.6528 0.5635 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5099(2) 0.70444(14) 0.37274(14) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.2882(2) 0.65768(15) 0.30661(16) 0.0260(3) Uani 1 1 d . . . . .
H7 H 0.1840 0.6333 0.3647 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2175(2) 0.64625(17) 0.15687(16) 0.0316(3) Uani 1 1 d . . . . .
H8 H 0.0653 0.6149 0.1133 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3677(2) 0.68038(17) 0.07054(16) 0.0317(3) Uani 1 1 d . . . . .
H9 H 0.3201 0.6706 -0.0327 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5883(2) 0.72897(17) 0.13642(16) 0.0303(3) Uani 1 1 d . . . . .
H10 H 0.6919 0.7541 0.0783 0.036 Uiso 1 1 calc R U . . .
C11 C 0.6592(2) 0.74125(15) 0.28633(15) 0.0254(3) Uani 1 1 d . . . . .
H11 H 0.8108 0.7750 0.3303 0.030 Uiso 1 1 calc R U . . .
N1 N 0.79856(17) 0.65529(12) 0.55254(12) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.8310 0.5813 0.4708 0.024 Uiso 1 1 calc R U . . .
O1 O 1.12428(14) 0.63207(11) 0.68528(10) 0.0252(2) Uani 1 1 d . . . . .
F1 F 1.06059(14) 0.96212(10) 0.81591(10) 0.0410(3) 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
C1 O1 1.2382(15) . ?
C1 N1 1.3325(16) . ?
C1 C2 1.5277(17) . ?
C2 F1 1.4061(15) . ?
C2 C3 1.5046(18) . ?
C3 C4 1.5197(18) . ?
C4 C5 1.5210(17) . ?
C5 N1 1.4731(15) . ?
C5 C6 1.5103(17) . ?
C6 C7 1.3897(18) . ?
C6 C11 1.3908(18) . ?
C7 C8 1.3866(19) . ?
C8 C9 1.384(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.3860(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
O1 C1 N1 122.98(11) . . ?
O1 C1 C2 119.02(11) . . ?
N1 C1 C2 117.99(11) . . ?
F1 C2 C3 109.28(11) . . ?
F1 C2 C1 105.26(10) . . ?
C3 C2 C1 114.57(11) . . ?
C2 C3 C4 110.54(11) . . ?
C3 C4 C5 108.93(11) . . ?
N1 C5 C6 110.21(10) . . ?
N1 C5 C4 109.99(10) . . ?
C6 C5 C4 113.18(10) . . ?
C7 C6 C11 118.71(12) . . ?
C7 C6 C5 119.32(11) . . ?
C11 C6 C5 121.95(11) . . ?
C8 C7 C6 120.74(13) . . ?
C9 C8 C7 120.29(13) . . ?
C8 C9 C10 119.25(13) . . ?
C9 C10 C11 120.56(13) . . ?
C10 C11 C6 120.43(12) . . ?
C1 N1 C5 126.83(10) . . ?

_refine_diff_density_max         0.23
_refine_diff_density_min         -0.20
_refine_diff_density_rms         0.03

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1006297'
