# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                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
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data_cu_pauline1b_0m

_audit_update_record             
;
2014-02-07 # Formatted by publCIF

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F N2 O'
_chemical_formula_sum            'C14 H9 F N2 O'
_chemical_formula_weight         240.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.76530(10)
_cell_length_b                   17.7911(4)
_cell_length_c                   16.0214(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.874(2)
_cell_angle_gamma                90
_cell_volume                     1071.90(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9053
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      68.38

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    0.900
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.959
_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      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15339
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.715
_diffrn_reflns_theta_max         68.371
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1971
_reflns_number_gt                1661
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0789P)²+0.9563P] 
 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     SHELXL
_refine_ls_extinction_coef       0.0028(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1971
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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
F1 F 0.2639(5) 0.54438(9) 0.56024(10) 0.0352(5) Uani 1 1 d . . . . .
O1 O 1.0874(6) 1.16556(12) 0.30002(13) 0.0381(6) Uani 1 1 d . . . . .
N1 N 0.6150(6) 0.87210(12) 0.44354(13) 0.0215(5) Uani 1 1 d . . . . .
N2 N 0.6337(6) 0.80594(12) 0.40176(13) 0.0213(5) Uani 1 1 d . . . . .
C1 C 0.9568(7) 1.12276(16) 0.34947(17) 0.0272(6) Uani 1 1 d . . . . .
H1 H 0.8791 1.1435 0.4001 0.033 Uiso 1 1 calc R U . . .
C4 C 0.9111(7) 1.04183(15) 0.33664(16) 0.0224(6) Uani 1 1 d . . . . .
C5 C 0.7742(7) 1.00121(15) 0.40042(16) 0.0216(6) Uani 1 1 d . . . . .
H5 H 0.7072 1.0250 0.4503 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7362(7) 0.92255(15) 0.38919(15) 0.0208(6) Uani 1 1 d . . . . .
C9 C 0.5353(7) 0.73814(15) 0.44202(16) 0.0216(6) Uani 1 1 d . . . . .
C10 C 0.5609(7) 0.73432(15) 0.52854(16) 0.0236(6) Uani 1 1 d . . . . .
H10 H 0.6425 0.7766 0.5602 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4681(7) 0.66912(16) 0.56870(17) 0.0258(6) Uani 1 1 d . . . . .
H11 H 0.4822 0.6661 0.6280 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3546(7) 0.60864(15) 0.52094(18) 0.0256(6) Uani 1 1 d . . . . .
C3 C 1.0126(7) 1.00724(16) 0.26087(16) 0.0242(6) Uani 1 1 d . . . . .
H3 H 1.1098 1.0372 0.2186 0.029 Uiso 1 1 calc R U . . .
C2 C 0.9718(7) 0.93207(16) 0.24860(16) 0.0249(6) Uani 1 1 d . . . . .
H2 H 1.0360 0.9094 0.1978 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8317(7) 0.88827(15) 0.31295(16) 0.0224(6) Uani 1 1 d . . . . .
C8 C 0.7603(7) 0.81254(15) 0.32423(16) 0.0233(6) Uani 1 1 d . . . . .
H8 H 0.7934 0.7731 0.2854 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4177(7) 0.67644(15) 0.39506(17) 0.0258(6) Uani 1 1 d . . . . .
H14 H 0.3987 0.6794 0.3358 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3289(7) 0.61092(16) 0.43503(18) 0.0278(6) Uani 1 1 d . . . . .
H13 H 0.2513 0.5681 0.4038 0.033 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
F1 C12 1.357(3) . ?
O1 C1 1.220(3) . ?
N1 C6 1.346(3) . ?
N1 N2 1.358(3) . ?
N2 C8 1.358(3) . ?
N2 C9 1.426(3) . ?
C1 C4 1.464(4) . ?
C1 H1 0.9500 . ?
C4 C5 1.373(4) . ?
C4 C3 1.430(4) . ?
C5 C6 1.417(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.427(4) . ?
C9 C10 1.386(4) . ?
C9 C14 1.390(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(4) . ?
C3 C2 1.359(4) . ?
C3 H3 0.9500 . ?
C2 C7 1.415(4) . ?
C2 H2 0.9500 . ?
C7 C8 1.387(4) . ?
C8 H8 0.9500 . ?
C14 C13 1.379(4) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?

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
C6 N1 N2 103.4(2) . . ?
N1 N2 C8 113.9(2) . . ?
N1 N2 C9 119.3(2) . . ?
C8 N2 C9 126.7(2) . . ?
O1 C1 C4 124.8(3) . . ?
O1 C1 H1 117.6 . . ?
C4 C1 H1 117.6 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 C1 117.3(2) . . ?
C3 C4 C1 120.5(2) . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
N1 C6 C5 127.7(2) . . ?
N1 C6 C7 112.1(2) . . ?
C5 C6 C7 120.2(2) . . ?
C10 C9 C14 120.4(2) . . ?
C10 C9 N2 119.1(2) . . ?
C14 C9 N2 120.4(2) . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
F1 C12 C13 118.8(2) . . ?
F1 C12 C11 118.6(2) . . ?
C13 C12 C11 122.5(3) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C2 C7 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C7 C2 H2 120.7 . . ?
C8 C7 C2 135.3(3) . . ?
C8 C7 C6 104.2(2) . . ?
C2 C7 C6 120.5(2) . . ?
N2 C8 C7 106.4(2) . . ?
N2 C8 H8 126.8 . . ?
C7 C8 H8 126.8 . . ?
C13 C14 C9 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?

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
C6 N1 N2 C8 0.0(3) . . . . ?
C6 N1 N2 C9 177.9(2) . . . . ?
O1 C1 C4 C5 177.0(3) . . . . ?
O1 C1 C4 C3 -1.8(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C1 C4 C5 C6 -178.7(2) . . . . ?
N2 N1 C6 C5 180.0(2) . . . . ?
N2 N1 C6 C7 0.0(3) . . . . ?
C4 C5 C6 N1 178.7(2) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
N1 N2 C9 C10 -25.7(3) . . . . ?
C8 N2 C9 C10 151.9(3) . . . . ?
N1 N2 C9 C14 154.8(2) . . . . ?
C8 N2 C9 C14 -27.6(4) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
N2 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 F1 179.9(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C5 C4 C3 C2 1.0(4) . . . . ?
C1 C4 C3 C2 179.8(2) . . . . ?
C4 C3 C2 C7 -1.0(4) . . . . ?
C3 C2 C7 C8 -178.4(3) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
N1 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 -180.0(2) . . . . ?
N1 C6 C7 C2 -178.7(2) . . . . ?
C5 C6 C7 C2 1.3(4) . . . . ?
N1 N2 C8 C7 0.0(3) . . . . ?
C9 N2 C8 C7 -177.8(2) . . . . ?
C2 C7 C8 N2 178.4(3) . . . . ?
C6 C7 C8 N2 0.0(3) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
N2 C9 C14 C13 179.0(2) . . . . ?
F1 C12 C13 C14 179.4(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C9 C14 C13 C12 0.9(4) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 986210'
