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# 
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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_a31209b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 F N2 O2'
_chemical_formula_weight         324.34

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   7.512(3)
_cell_length_b                   16.751(6)
_cell_length_c                   26.703(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3360(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    956
_cell_measurement_theta_min      2.548
_cell_measurement_theta_max      25.292

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15148
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.525
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3636
_reflns_number_gt                1871
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0512P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3636
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_restrained_S_all      0.879
_refine_ls_shift/su_max          0.002
_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 0.9704(2) 0.36702(8) 0.24308(4) 0.1022(5) Uani 1 1 d . . . . .
N1 N 0.4415(2) 0.35712(9) 0.08953(6) 0.0592(4) Uani 1 1 d . . . . .
N2 N 0.7917(2) 0.28313(9) 0.04999(6) 0.0536(4) Uani 1 1 d . . . . .
O1 O 0.31254(16) 0.40938(8) 0.06871(5) 0.0709(4) Uani 1 1 d . . . . .
O2 O 1.01429(19) 0.19928(9) 0.02439(5) 0.0691(4) Uani 1 1 d . . . . .
C1 C 0.7353(2) 0.35854(10) 0.12513(6) 0.0467(4) Uani 1 1 d . . . . .
C2 C 0.8427(2) 0.30470(10) 0.09890(6) 0.0464(4) Uani 1 1 d . . . . .
C3 C 0.9939(3) 0.27449(12) 0.12158(7) 0.0588(5) Uani 1 1 d . . . . .
H3 H 1.0665 0.2393 0.1040 0.071 Uiso 1 1 calc R U . . .
C4 C 1.0382(3) 0.29587(13) 0.16983(8) 0.0674(6) Uani 1 1 d . . . . .
H4 H 1.1408 0.2760 0.1848 0.081 Uiso 1 1 calc R U . . .
C5 C 0.9293(3) 0.34650(13) 0.19513(7) 0.0659(6) Uani 1 1 d . . . . .
C6 C 0.7812(3) 0.37906(12) 0.17382(7) 0.0604(5) Uani 1 1 d . . . . .
H6 H 0.7113 0.4148 0.1918 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5785(2) 0.39777(10) 0.10235(6) 0.0477(4) Uani 1 1 d . . . . .
C8 C 0.5643(2) 0.48355(11) 0.09034(7) 0.0534(5) Uani 1 1 d . . . . .
C9 C 0.6680(3) 0.54810(12) 0.11523(9) 0.0758(6) Uani 1 1 d . . . . .
H9A H 0.6101 0.5993 0.1198 0.091 Uiso 1 1 calc R U . . .
H9B H 0.7483 0.5329 0.1420 0.091 Uiso 1 1 calc R U . . .
C10 C 0.7165(3) 0.52464(13) 0.06368(9) 0.0771(6) Uani 1 1 d . . . . .
H10A H 0.8259 0.4948 0.0590 0.093 Uiso 1 1 calc R U . . .
H10B H 0.6874 0.5613 0.0368 0.093 Uiso 1 1 calc R U . . .
C11 C 0.3718(3) 0.49220(11) 0.07434(7) 0.0584(5) Uani 1 1 d . . . . .
H11 H 0.3665 0.5192 0.0418 0.070 Uiso 1 1 calc R U . . .
C12 C 0.2543(2) 0.53530(10) 0.11103(7) 0.0534(5) Uani 1 1 d . . . . .
C13 C 0.1766(2) 0.60665(11) 0.09837(8) 0.0641(5) Uani 1 1 d . . . . .
H13 H 0.1913 0.6267 0.0662 0.077 Uiso 1 1 calc R U . . .
C14 C 0.0767(3) 0.64929(12) 0.13279(10) 0.0753(6) Uani 1 1 d . . . . .
H14 H 0.0280 0.6981 0.1234 0.090 Uiso 1 1 calc R U . . .
C15 C 0.0482(3) 0.62146(13) 0.17985(9) 0.0703(6) Uani 1 1 d . . . . .
C16 C 0.1235(3) 0.54966(14) 0.19248(8) 0.0804(7) Uani 1 1 d . . . . .
H16 H 0.1064 0.5295 0.2246 0.096 Uiso 1 1 calc R U . . .
C17 C 0.2243(3) 0.50667(13) 0.15866(8) 0.0737(6) Uani 1 1 d . . . . .
H17 H 0.2725 0.4578 0.1682 0.088 Uiso 1 1 calc R U . . .
C18 C -0.0629(3) 0.66775(16) 0.21702(11) 0.1156(10) Uani 1 1 d . . . . .
H18A H -0.0505 0.6444 0.2497 0.173 Uiso 1 1 calc R U . . .
H18B H -0.1856 0.6661 0.2070 0.173 Uiso 1 1 calc R U . . .
H18C H -0.0231 0.7222 0.2180 0.173 Uiso 1 1 calc R U . . .
C19 C 0.8749(3) 0.23443(11) 0.01759(7) 0.0570(5) Uani 1 1 d . . . . .
H19 H 0.8200 0.2268 -0.0133 0.068 Uiso 1 1 calc R U . . .
H2 H 0.689(3) 0.3029(11) 0.0386(7) 0.065(6) Uiso 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 C5 1.361(2) . ?
N1 C7 1.280(2) . ?
N1 O1 1.4192(18) . ?
N2 C19 1.343(2) . ?
N2 C2 1.408(2) . ?
N2 H2 0.892(19) . ?
O1 C11 1.465(2) . ?
O2 C19 1.215(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.398(2) . ?
C1 C7 1.480(2) . ?
C2 C3 1.383(2) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.476(2) . ?
C8 C9 1.489(3) . ?
C8 C10 1.513(3) . ?
C8 C11 1.514(3) . ?
C9 C10 1.477(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.503(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.373(2) . ?
C12 C17 1.378(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 C18 1.511(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 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
C7 N1 O1 108.99(14) . . ?
C19 N2 C2 128.80(17) . . ?
C19 N2 H2 114.1(12) . . ?
C2 N2 H2 117.1(12) . . ?
N1 O1 C11 109.65(13) . . ?
C6 C1 C2 119.04(17) . . ?
C6 C1 C7 118.23(16) . . ?
C2 C1 C7 122.68(15) . . ?
C3 C2 C1 119.38(16) . . ?
C3 C2 N2 122.38(17) . . ?
C1 C2 N2 118.23(16) . . ?
C4 C3 C2 120.85(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.79(19) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 F1 119.27(19) . . ?
C4 C5 C6 122.26(18) . . ?
F1 C5 C6 118.5(2) . . ?
C5 C6 C1 119.64(18) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C8 113.67(16) . . ?
N1 C7 C1 120.89(16) . . ?
C8 C7 C1 125.40(16) . . ?
C7 C8 C9 124.88(16) . . ?
C7 C8 C10 119.37(16) . . ?
C9 C8 C10 58.94(13) . . ?
C7 C8 C11 102.91(15) . . ?
C9 C8 C11 123.77(16) . . ?
C10 C8 C11 123.06(17) . . ?
C10 C9 C8 61.31(14) . . ?
C10 C9 H9A 117.6 . . ?
C8 C9 H9A 117.6 . . ?
C10 C9 H9B 117.6 . . ?
C8 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
C9 C10 C8 59.75(13) . . ?
C9 C10 H10A 117.8 . . ?
C8 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
C8 C10 H10B 117.8 . . ?
H10A C10 H10B 114.9 . . ?
O1 C11 C12 110.08(15) . . ?
O1 C11 C8 103.21(14) . . ?
C12 C11 C8 115.01(15) . . ?
O1 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
C8 C11 H11 109.4 . . ?
C13 C12 C17 117.45(19) . . ?
C13 C12 C11 120.49(18) . . ?
C17 C12 C11 122.04(17) . . ?
C12 C13 C14 121.1(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 121.5(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 117.6(2) . . ?
C14 C15 C18 121.3(2) . . ?
C16 C15 C18 121.1(2) . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C12 C17 C16 120.8(2) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 N2 126.79(19) . . ?
O2 C19 H19 116.6 . . ?
N2 C19 H19 116.6 . . ?

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
C7 N1 O1 C11 -6.46(19) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 C1 C2 C3 175.69(16) . . . . ?
C6 C1 C2 N2 178.51(16) . . . . ?
C7 C1 C2 N2 -4.4(2) . . . . ?
C19 N2 C2 C3 -1.7(3) . . . . ?
C19 N2 C2 C1 178.40(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
N2 C2 C3 C4 -178.90(17) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 F1 178.99(18) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
F1 C5 C6 C1 -179.37(17) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C7 C1 C6 C5 -177.25(17) . . . . ?
O1 N1 C7 C8 -2.0(2) . . . . ?
O1 N1 C7 C1 -179.80(14) . . . . ?
C6 C1 C7 N1 -116.62(19) . . . . ?
C2 C1 C7 N1 66.3(2) . . . . ?
C6 C1 C7 C8 65.9(2) . . . . ?
C2 C1 C7 C8 -111.2(2) . . . . ?
N1 C7 C8 C9 157.92(19) . . . . ?
C1 C7 C8 C9 -24.4(3) . . . . ?
N1 C7 C8 C10 -131.31(18) . . . . ?
C1 C7 C8 C10 46.3(3) . . . . ?
N1 C7 C8 C11 9.2(2) . . . . ?
C1 C7 C8 C11 -173.19(15) . . . . ?
C7 C8 C9 C10 106.1(2) . . . . ?
C11 C8 C9 C10 -111.3(2) . . . . ?
C7 C8 C10 C9 -115.28(19) . . . . ?
C11 C8 C10 C9 112.5(2) . . . . ?
N1 O1 C11 C12 -111.64(16) . . . . ?
N1 O1 C11 C8 11.60(18) . . . . ?
C7 C8 C11 O1 -11.85(18) . . . . ?
C9 C8 C11 O1 -161.06(18) . . . . ?
C10 C8 C11 O1 126.72(19) . . . . ?
C7 C8 C11 C12 108.06(17) . . . . ?
C9 C8 C11 C12 -41.2(3) . . . . ?
C10 C8 C11 C12 -113.4(2) . . . . ?
O1 C11 C12 C13 -127.80(18) . . . . ?
C8 C11 C12 C13 116.2(2) . . . . ?
O1 C11 C12 C17 54.1(2) . . . . ?
C8 C11 C12 C17 -61.9(2) . . . . ?
C17 C12 C13 C14 2.0(3) . . . . ?
C11 C12 C13 C14 -176.15(18) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C13 C14 C15 C18 -179.2(2) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C18 C15 C16 C17 179.6(2) . . . . ?
C13 C12 C17 C16 -1.6(3) . . . . ?
C11 C12 C17 C16 176.5(2) . . . . ?
C15 C16 C17 C12 0.8(4) . . . . ?
C2 N2 C19 O2 -0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.892(19) 2.135(19) 2.894(2) 142.4(16) 4_455

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 995733'
