# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exp_1470
_database_code_depnum_ccdc_archive 'CCDC 1507666'
_audit_update_record             
;
2016-10-01 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F N O'
_chemical_formula_weight         62.03

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      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                   12.1928(12)
_cell_length_b                   8.0344(6)
_cell_length_c                   14.1806(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.454(9)
_cell_angle_gamma                90
_cell_volume                     1351.0(2)
_cell_formula_units_Z            6
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.457
_exptl_crystal_F_000             186
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.051
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5990
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         29.254
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3086
_reflns_number_gt                1979
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0410P)²+0.0820P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.69494(8) 0.61987(12) 0.02938(8) 0.0645(3) Uani 1 1 d . . . . .
F2 F 0.59048(8) 0.44019(13) -0.06630(8) 0.0646(3) Uani 1 1 d . . . . .
O3 O 0.57150(9) 0.25571(14) 0.07891(8) 0.0492(3) Uani 1 1 d . . . . .
N4 N 0.91139(11) 0.47775(16) 0.15042(9) 0.0412(3) Uani 1 1 d . . . . .
H4 H 0.8657 0.5395 0.1729 0.049 Uiso 1 1 calc R U . . .
C5 C 0.88426(13) 0.38949(18) 0.06462(11) 0.0370(4) Uani 1 1 d . . . . .
C6 C 1.02347(13) 0.45114(18) 0.19446(12) 0.0388(4) Uani 1 1 d . . . . .
O7 O 0.67033(11) 0.44309(17) 0.18108(10) 0.0648(4) Uani 1 1 d . . . . .
C8 C 0.98267(13) 0.30790(18) 0.05175(12) 0.0374(4) Uani 1 1 d . . . . .
C9 C 1.07071(13) 0.34541(18) 0.13567(12) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.78128(13) 0.3713(2) -0.00226(12) 0.0398(4) Uani 1 1 d . . . . .
C11 C 0.97684(16) 0.2111(2) -0.03051(13) 0.0477(4) Uani 1 1 d . . . . .
H11 H 1.0410 0.1582 -0.0406 0.057 Uiso 1 1 calc R U . . .
C12 C 1.08629(15) 0.5082(2) 0.28297(13) 0.0483(4) Uani 1 1 d . . . . .
H12 H 1.0551 0.5803 0.3209 0.058 Uiso 1 1 calc R U . . .
C13 C 1.18216(14) 0.2936(2) 0.16794(14) 0.0495(5) Uani 1 1 d . . . . .
H13 H 1.2147 0.2232 0.1300 0.059 Uiso 1 1 calc R U . . .
C14 C 0.67666(14) 0.4531(2) 0.01350(13) 0.0470(4) Uani 1 1 d . . . . .
C15 C 0.87578(16) 0.1944(2) -0.09649(13) 0.0540(5) Uani 1 1 d . . . . .
H15 H 0.8719 0.1300 -0.1517 0.065 Uiso 1 1 calc R U . . .
C16 C 0.77910(15) 0.2718(2) -0.08250(13) 0.0492(5) Uani 1 1 d . . . . .
H16 H 0.7114 0.2565 -0.1279 0.059 Uiso 1 1 calc R U . . .
C17 C 0.63821(13) 0.3858(2) 0.10193(13) 0.0442(4) Uani 1 1 d . . . . .
C18 C 0.52717(16) 0.1853(2) 0.15744(14) 0.0567(5) Uani 1 1 d . . . . .
H18A H 0.4854 0.2692 0.1836 0.068 Uiso 1 1 calc R U . . .
H18B H 0.5886 0.1465 0.2092 0.068 Uiso 1 1 calc R U . . .
C19 C 1.24321(15) 0.3476(2) 0.25632(15) 0.0567(5) Uani 1 1 d . . . . .
H19 H 1.3172 0.3119 0.2788 0.068 Uiso 1 1 calc R U . . .
C20 C 1.19589(15) 0.4552(2) 0.31280(14) 0.0552(5) Uani 1 1 d . . . . .
H20 H 1.2394 0.4919 0.3719 0.066 Uiso 1 1 calc R U . . .
C21 C 0.45200(18) 0.0444(3) 0.11750(16) 0.0713(6) Uani 1 1 d . . . . .
H21A H 0.3946 0.0824 0.0634 0.107 Uiso 1 1 calc R U . . .
H21B H 0.4174 0.0015 0.1668 0.107 Uiso 1 1 calc R U . . .
H21C H 0.4953 -0.0418 0.0965 0.107 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 C14 1.3686(19) . ?
F2 C14 1.3572(19) . ?
O3 C17 1.318(2) . ?
O3 C18 1.4605(19) . ?
N4 C5 1.380(2) . ?
N4 C6 1.381(2) . ?
C5 C10 1.394(2) . ?
C5 C8 1.416(2) . ?
C6 C12 1.387(2) . ?
C6 C9 1.404(2) . ?
O7 C17 1.192(2) . ?
C8 C11 1.390(2) . ?
C8 C9 1.437(2) . ?
C9 C13 1.393(2) . ?
C10 C16 1.386(2) . ?
C10 C14 1.497(2) . ?
C11 C15 1.369(2) . ?
C12 C20 1.372(2) . ?
C13 C19 1.371(3) . ?
C14 C17 1.536(2) . ?
C15 C16 1.387(2) . ?
C18 C21 1.483(3) . ?
C19 C20 1.391(3) . ?

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
C17 O3 C18 115.79(13) . . ?
C5 N4 C6 109.15(13) . . ?
N4 C5 C10 130.29(14) . . ?
N4 C5 C8 108.37(14) . . ?
C10 C5 C8 121.33(15) . . ?
N4 C6 C12 129.64(15) . . ?
N4 C6 C9 108.94(14) . . ?
C12 C6 C9 121.38(16) . . ?
C11 C8 C5 119.20(16) . . ?
C11 C8 C9 134.02(16) . . ?
C5 C8 C9 106.75(14) . . ?
C13 C9 C6 119.31(16) . . ?
C13 C9 C8 133.87(15) . . ?
C6 C9 C8 106.74(14) . . ?
C16 C10 C5 117.46(15) . . ?
C16 C10 C14 121.43(16) . . ?
C5 C10 C14 121.09(15) . . ?
C15 C11 C8 119.37(17) . . ?
C20 C12 C6 117.98(17) . . ?
C19 C13 C9 119.09(17) . . ?
F2 C14 F1 106.07(13) . . ?
F2 C14 C10 111.31(14) . . ?
F1 C14 C10 110.03(13) . . ?
F2 C14 C17 109.25(13) . . ?
F1 C14 C17 106.22(14) . . ?
C10 C14 C17 113.57(14) . . ?
C11 C15 C16 121.18(16) . . ?
C10 C16 C15 121.43(17) . . ?
O7 C17 O3 126.04(16) . . ?
O7 C17 C14 122.47(16) . . ?
O3 C17 C14 111.41(15) . . ?
O3 C18 C21 108.05(15) . . ?
C13 C19 C20 120.89(17) . . ?
C12 C20 C19 121.32(18) . . ?

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 N4 C5 C10 176.82(15) . . . . ?
C6 N4 C5 C8 -1.82(16) . . . . ?
C5 N4 C6 C12 -177.14(16) . . . . ?
C5 N4 C6 C9 0.81(16) . . . . ?
N4 C5 C8 C11 -179.61(13) . . . . ?
C10 C5 C8 C11 1.6(2) . . . . ?
N4 C5 C8 C9 2.08(16) . . . . ?
C10 C5 C8 C9 -176.70(13) . . . . ?
N4 C6 C9 C13 -176.60(13) . . . . ?
C12 C6 C9 C13 1.6(2) . . . . ?
N4 C6 C9 C8 0.49(17) . . . . ?
C12 C6 C9 C8 178.65(14) . . . . ?
C11 C8 C9 C13 -3.0(3) . . . . ?
C5 C8 C9 C13 174.91(16) . . . . ?
C11 C8 C9 C6 -179.52(16) . . . . ?
C5 C8 C9 C6 -1.57(16) . . . . ?
N4 C5 C10 C16 -179.21(15) . . . . ?
C8 C5 C10 C16 -0.7(2) . . . . ?
N4 C5 C10 C14 -0.6(2) . . . . ?
C8 C5 C10 C14 177.83(14) . . . . ?
C5 C8 C11 C15 -1.1(2) . . . . ?
C9 C8 C11 C15 176.65(16) . . . . ?
N4 C6 C12 C20 176.26(15) . . . . ?
C9 C6 C12 C20 -1.5(2) . . . . ?
C6 C9 C13 C19 -0.2(2) . . . . ?
C8 C9 C13 C19 -176.36(16) . . . . ?
C16 C10 C14 F2 -10.7(2) . . . . ?
C5 C10 C14 F2 170.84(13) . . . . ?
C16 C10 C14 F1 -127.93(16) . . . . ?
C5 C10 C14 F1 53.6(2) . . . . ?
C16 C10 C14 C17 113.15(18) . . . . ?
C5 C10 C14 C17 -65.35(19) . . . . ?
C8 C11 C15 C16 -0.3(3) . . . . ?
C5 C10 C16 C15 -0.7(2) . . . . ?
C14 C10 C16 C15 -179.21(15) . . . . ?
C11 C15 C16 C10 1.2(3) . . . . ?
C18 O3 C17 O7 4.9(3) . . . . ?
C18 O3 C17 C14 -178.11(14) . . . . ?
F2 C14 C17 O7 -145.77(17) . . . . ?
F1 C14 C17 O7 -31.8(2) . . . . ?
C10 C14 C17 O7 89.3(2) . . . . ?
F2 C14 C17 O3 37.11(18) . . . . ?
F1 C14 C17 O3 151.12(13) . . . . ?
C10 C14 C17 O3 -87.81(17) . . . . ?
C17 O3 C18 C21 178.40(15) . . . . ?
C9 C13 C19 C20 -1.1(3) . . . . ?
C6 C12 C20 C19 0.1(3) . . . . ?
C13 C19 C20 C12 1.2(3) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_exp_2298
_database_code_depnum_ccdc_archive 'CCDC 1507706'
_audit_update_record             
;
2016-10-01 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_audit_creation_date             2016-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 F2 N O'
_chemical_formula_sum            'C11 H10 F0.25 N O'
_chemical_formula_weight         176.95
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4538(8)
_cell_length_b                   9.4567(7)
_cell_length_c                   10.8021(8)
_cell_angle_alpha                89.874(6)
_cell_angle_beta                 74.590(8)
_cell_angle_gamma                81.932(7)
_cell_volume                     823.73(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9620
_cell_measurement_theta_min      2.9740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             373
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.091
_diffrn_reflns_theta_min         2.750
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0302516000
_diffrn_orient_matrix_UB_12      0.0696680000
_diffrn_orient_matrix_UB_13      0.0279395000
_diffrn_orient_matrix_UB_21      -0.0055937000
_diffrn_orient_matrix_UB_22      0.0255024000
_diffrn_orient_matrix_UB_23      -0.0607141000
_diffrn_orient_matrix_UB_31      -0.0824057000
_diffrn_orient_matrix_UB_32      -0.0155757000
_diffrn_orient_matrix_UB_33      0.0133668000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             3757
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.0928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1388
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), C11(H11), C23(H23), C24(H24), N6(H6), C16(H16), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.12665(15) 0.32624(14) 0.62289(11) 0.0576(4) Uani 1 1 d . . . . .
F2 F 0.09873(16) 0.14213(13) 0.74116(13) 0.0610(4) Uani 1 1 d . . . . .
O7 O -0.07226(19) 0.40538(16) 0.88454(14) 0.0575(4) Uani 1 1 d . . . . .
C9 C 0.1630(3) 0.2669(2) 0.72860(19) 0.0420(5) Uani 1 1 d . . . . .
N10 N 0.1964(2) 0.39662(18) 0.89911(16) 0.0469(4) Uani 1 1 d . . . . .
H10 H 0.1791 0.4501 0.9671 0.056 Uiso 1 1 calc R . . . .
C11 C 0.4793(3) 0.1757(2) 0.6418(2) 0.0459(5) Uani 1 1 d . . . . .
H11 H 0.4688 0.1228 0.5727 0.055 Uiso 1 1 calc R . . . .
C12 C 0.3410(2) 0.2510(2) 0.72480(18) 0.0396(5) Uani 1 1 d . . . . .
C17 C 0.0763(3) 0.3663(2) 0.84763(19) 0.0437(5) Uani 1 1 d . . . . .
C18 C 0.6349(3) 0.1788(2) 0.6615(2) 0.0499(5) Uani 1 1 d . . . . .
C19 C 0.3541(3) 0.3302(2) 0.82821(19) 0.0419(5) Uani 1 1 d . . . . .
C23 C 0.6437(3) 0.2593(2) 0.7657(2) 0.0555(6) Uani 1 1 d . . . . .
H23 H 0.7473 0.2624 0.7794 0.067 Uiso 1 1 calc R . . . .
C24 C 0.5062(3) 0.3351(2) 0.8504(2) 0.0541(6) Uani 1 1 d . . . . .
H24 H 0.5160 0.3875 0.9201 0.065 Uiso 1 1 calc R . . . .
C26 C 0.7877(3) 0.0967(3) 0.5728(2) 0.0719(8) Uani 1 1 d . . . . .
H26A H 0.7836 -0.0039 0.5812 0.108 Uiso 1 1 calc GR . . . .
H26B H 0.8841 0.1198 0.5948 0.108 Uiso 1 1 calc GR . . . .
H26C H 0.7931 0.1217 0.4858 0.108 Uiso 1 1 calc GR . . . .
F3 F 0.29466(17) 0.70538(15) 0.87087(12) 0.0694(4) Uani 1 1 d . . . . .
F4 F 0.31343(17) 0.87191(13) 0.73291(14) 0.0698(4) Uani 1 1 d . . . . .
O5 O 0.31588(19) 0.59747(16) 0.61112(14) 0.0556(4) Uani 1 1 d . . . . .
N6 N 0.5883(2) 0.59553(17) 0.61227(15) 0.0456(4) Uani 1 1 d . . . . .
H6 H 0.6356 0.5333 0.5510 0.055 Uiso 1 1 calc R . . . .
C8 C 0.6750(3) 0.6662(2) 0.68265(18) 0.0418(5) Uani 1 1 d . . . . .
C13 C 0.5646(2) 0.7609(2) 0.77293(18) 0.0404(5) Uani 1 1 d . . . . .
C14 C 0.7876(3) 0.8326(2) 0.8440(2) 0.0500(5) Uani 1 1 d . . . . .
C15 C 0.3959(3) 0.7490(2) 0.7620(2) 0.0456(5) Uani 1 1 d . . . . .
C16 C 0.6190(3) 0.8437(2) 0.8528(2) 0.0487(5) Uani 1 1 d . . . . .
H16 H 0.5433 0.9072 0.9128 0.058 Uiso 1 1 calc R . . . .
C20 C 0.4250(3) 0.6363(2) 0.65162(19) 0.0424(5) Uani 1 1 d . . . . .
C21 C 0.8422(3) 0.6518(2) 0.6719(2) 0.0545(6) Uani 1 1 d . . . . .
H21 H 0.9174 0.5880 0.6118 0.065 Uiso 1 1 calc R . . . .
C22 C 0.8945(3) 0.7356(3) 0.7534(2) 0.0556(6) Uani 1 1 d . . . . .
H22 H 1.0074 0.7263 0.7472 0.067 Uiso 1 1 calc R . . . .
C25 C 0.8501(3) 0.9235(3) 0.9286(2) 0.0677(7) Uani 1 1 d . . . . .
H25A H 0.8417 1.0202 0.9011 0.102 Uiso 1 1 calc GR . . . .
H25B H 0.9639 0.8878 0.9231 0.102 Uiso 1 1 calc GR . . . .
H25C H 0.7847 0.9209 1.0159 0.102 Uiso 1 1 calc GR . . . .


_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 C9 1.360(2) . ?
F2 C9 1.359(2) . ?
O7 C17 1.216(2) . ?
C9 C12 1.481(3) . ?
C9 C17 1.544(3) . ?
N10 C17 1.343(3) . ?
N10 C19 1.408(3) . ?
C11 C12 1.374(3) . ?
C11 C18 1.392(3) . ?
C12 C19 1.383(3) . ?
C18 C23 1.384(3) . ?
C18 C26 1.501(3) . ?
C19 C24 1.376(3) . ?
C23 C24 1.381(3) . ?
F3 C15 1.359(2) . ?
F4 C15 1.351(2) . ?
O5 C20 1.219(2) . ?
N6 C8 1.413(3) . ?
N6 C20 1.333(3) . ?
C8 C13 1.382(3) . ?
C8 C21 1.374(3) . ?
C13 C15 1.481(3) . ?
C13 C16 1.372(3) . ?
C14 C16 1.392(3) . ?
C14 C22 1.384(3) . ?
C14 C25 1.497(3) . ?
C15 C20 1.547(3) . ?
C21 C22 1.381(3) . ?

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 C9 C12 114.28(16) . . ?
F1 C9 C17 109.41(16) . . ?
F2 C9 F1 105.22(16) . . ?
F2 C9 C12 114.16(17) . . ?
F2 C9 C17 109.53(16) . . ?
C12 C9 C17 104.21(16) . . ?
C17 N10 C19 111.73(17) . . ?
C12 C11 C18 119.9(2) . . ?
C11 C12 C9 131.81(19) . . ?
C11 C12 C19 120.9(2) . . ?
C19 C12 C9 107.29(17) . . ?
O7 C17 C9 124.83(19) . . ?
O7 C17 N10 128.8(2) . . ?
N10 C17 C9 106.40(17) . . ?
C11 C18 C26 120.9(2) . . ?
C23 C18 C11 117.8(2) . . ?
C23 C18 C26 121.3(2) . . ?
C12 C19 N10 110.37(18) . . ?
C24 C19 N10 129.00(19) . . ?
C24 C19 C12 120.6(2) . . ?
C24 C23 C18 123.2(2) . . ?
C19 C24 C23 117.6(2) . . ?
C20 N6 C8 112.34(16) . . ?
C13 C8 N6 109.88(18) . . ?
C21 C8 N6 129.61(19) . . ?
C21 C8 C13 120.5(2) . . ?
C8 C13 C15 107.31(18) . . ?
C16 C13 C8 121.0(2) . . ?
C16 C13 C15 131.71(19) . . ?
C16 C14 C25 121.0(2) . . ?
C22 C14 C16 117.4(2) . . ?
C22 C14 C25 121.6(2) . . ?
F3 C15 C13 113.58(18) . . ?
F3 C15 C20 109.84(16) . . ?
F4 C15 F3 105.61(17) . . ?
F4 C15 C13 114.15(17) . . ?
F4 C15 C20 109.36(17) . . ?
C13 C15 C20 104.29(16) . . ?
C13 C16 C14 120.1(2) . . ?
O5 C20 N6 128.99(19) . . ?
O5 C20 C15 124.84(19) . . ?
N6 C20 C15 106.16(17) . . ?
C8 C21 C22 117.7(2) . . ?
C21 C22 C14 123.4(2) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.882
####################################################################### 
# 
# 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_exp_2607
_database_code_depnum_ccdc_archive 'CCDC 1507707'
_audit_update_record             
;
2016-10-01 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_audit_creation_date             2016-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H7 F2 N O'
_chemical_formula_sum            'C11 H10 F0.25 N O'
_chemical_formula_weight         176.95
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9946(10)
_cell_length_b                   7.5522(7)
_cell_length_c                   11.4653(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.431(9)
_cell_angle_gamma                90
_cell_volume                     944.01(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1956
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8550
_cell_measurement_theta_min      3.5850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             373
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7081
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.250
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002118000
_diffrn_orient_matrix_UB_12      0.0933237000
_diffrn_orient_matrix_UB_13      0.0068718000
_diffrn_orient_matrix_UB_21      -0.0570314000
_diffrn_orient_matrix_UB_22      -0.0053962000
_diffrn_orient_matrix_UB_23      0.0224252000
_diffrn_orient_matrix_UB_31      0.0313365000
_diffrn_orient_matrix_UB_32      -0.0089375000
_diffrn_orient_matrix_UB_33      0.0578217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1605
_reflns_number_total             2259
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C3(H3), C2(H2), C7(H7), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F2 F 0.21985(10) 0.25481(12) 0.42587(9) 0.0594(3) Uani 1 1 d . . . . .
F1 F 0.37901(9) 0.37899(14) 0.52258(9) 0.0598(3) Uani 1 1 d . . . . .
C10 C 0.18873(13) 0.51940(19) 0.53416(13) 0.0383(4) Uani 1 1 d . . . . .
C1 C 0.17659(13) 0.6834(2) 0.48442(13) 0.0401(4) Uani 1 1 d . . . . .
N1 N 0.23343(13) 0.69130(18) 0.38106(12) 0.0476(4) Uani 1 1 d . . . . .
H1 H 0.2372 0.7845 0.3385 0.057 Uiso 1 1 calc R . . . .
O1 O 0.32789(13) 0.48951(17) 0.27291(11) 0.0615(4) Uani 1 1 d . . . . .
C9 C 0.13563(13) 0.4780(2) 0.63639(13) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.13987(15) 0.3093(2) 0.68866(14) 0.0470(4) Uani 1 1 d . . . . .
H8 H 0.1824 0.2180 0.6575 0.056 Uiso 1 1 calc R . . . .
C4 C 0.07128(14) 0.6169(2) 0.68490(14) 0.0441(4) Uani 1 1 d . . . . .
C3 C 0.06503(14) 0.7856(2) 0.63222(15) 0.0483(4) Uani 1 1 d . . . . .
H3 H 0.0247 0.8759 0.6668 0.058 Uiso 1 1 calc R . . . .
C2 C 0.11565(15) 0.8216(2) 0.53275(15) 0.0483(4) Uani 1 1 d . . . . .
H2 H 0.1099 0.9335 0.4985 0.058 Uiso 1 1 calc R . . . .
C12 C 0.28077(15) 0.5334(2) 0.35833(14) 0.0458(4) Uani 1 1 d . . . . .
C11 C 0.26533(14) 0.4141(2) 0.46391(14) 0.0427(4) Uani 1 1 d . . . . .
C7 C 0.08198(16) 0.2792(3) 0.78456(16) 0.0576(5) Uani 1 1 d . . . . .
H7 H 0.0841 0.1670 0.8181 0.069 Uiso 1 1 calc R . . . .
C5 C 0.01446(16) 0.5799(3) 0.78558(16) 0.0560(5) Uani 1 1 d . . . . .
H5 H -0.0269 0.6695 0.8198 0.067 Uiso 1 1 calc R . . . .
C6 C 0.01933(17) 0.4157(3) 0.83308(16) 0.0633(5) Uani 1 1 d . . . . .
H6 H -0.0196 0.3935 0.8989 0.076 Uiso 1 1 calc R . . . .


_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
F2 C11 1.3533(17) . ?
F1 C11 1.3666(18) . ?
C10 C1 1.363(2) . ?
C10 C9 1.410(2) . ?
C10 C11 1.472(2) . ?
C1 N1 1.411(2) . ?
C1 C2 1.393(2) . ?
N1 C12 1.340(2) . ?
O1 C12 1.2119(19) . ?
C9 C8 1.406(2) . ?
C9 C4 1.418(2) . ?
C8 C7 1.359(2) . ?
C4 C3 1.408(2) . ?
C4 C5 1.410(2) . ?
C3 C2 1.360(2) . ?
C12 C11 1.536(2) . ?
C7 C6 1.395(3) . ?
C5 C6 1.353(3) . ?

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 C10 C9 121.37(13) . . ?
C1 C10 C11 107.09(13) . . ?
C9 C10 C11 131.51(14) . . ?
C10 C1 N1 111.10(13) . . ?
C10 C1 C2 122.73(15) . . ?
C2 C1 N1 126.17(14) . . ?
C12 N1 C1 110.55(13) . . ?
C10 C9 C4 116.30(14) . . ?
C8 C9 C10 124.09(14) . . ?
C8 C9 C4 119.58(15) . . ?
C7 C8 C9 120.18(17) . . ?
C3 C4 C9 120.00(14) . . ?
C3 C4 C5 121.89(16) . . ?
C5 C4 C9 118.10(16) . . ?
C2 C3 C4 122.57(14) . . ?
C3 C2 C1 116.98(15) . . ?
N1 C12 C11 106.46(13) . . ?
O1 C12 N1 128.16(16) . . ?
O1 C12 C11 125.37(15) . . ?
F2 C11 F1 105.20(12) . . ?
F2 C11 C10 116.29(13) . . ?
F2 C11 C12 109.97(13) . . ?
F1 C11 C10 112.78(13) . . ?
F1 C11 C12 108.33(12) . . ?
C10 C11 C12 104.12(12) . . ?
C8 C7 C6 120.45(18) . . ?
C6 C5 C4 120.84(17) . . ?
C5 C6 C7 120.84(17) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.760
_oxdiff_exptl_absorpt_empirical_full_min 0.634
