# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_F2_23_294K
_database_code_depnum_ccdc_archive 'CCDC 1453270'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(F2_23 or 11-059)'
_chemical_name_common            ?
_chemical_melting_point          388
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   4.99550(10)
_cell_length_b                   17.1031(4)
_cell_length_c                   13.0176(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.380(2)
_cell_angle_gamma                90
_cell_volume                     1094.00(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3105
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.67

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.630
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            9209
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         27.706
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.713
_diffrn_reflns_point_group_measured_fraction_full 0.763
_reflns_number_total             3670
_reflns_number_gt                2456
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.491
_reflns_Friedel_fraction_max     0.472
_reflns_Friedel_fraction_full    0.526
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0546P)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_abs_structure_details 
;
Flack x from 642 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3670
_refine_ls_number_parameters     315
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.031

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
F22A F 0.2164(5) 0.48341(13) 0.11549(16) 0.0750(7) Uani 1 1 d . . . . .
F23A F 0.0982(6) 0.58883(14) -0.0348(2) 0.0893(8) Uani 1 1 d . . . . .
O1A O 0.1507(5) 0.32340(16) 0.1030(2) 0.0674(7) Uani 1 1 d . . . . .
C1A C 0.3930(6) 0.3175(2) 0.1395(3) 0.0487(9) Uani 1 1 d . . . . .
N1A N 0.5829(6) 0.36151(19) 0.1045(3) 0.0508(8) Uani 1 1 d . . . . .
H1A H 0.742(10) 0.350(2) 0.122(3) 0.071(13) Uiso 1 1 d . . . . .
C11A C 0.4945(7) 0.2633(2) 0.2269(3) 0.0496(9) Uani 1 1 d . . . . .
C12A C 0.3411(9) 0.1979(3) 0.2384(3) 0.0665(11) Uani 1 1 d . . . . .
H12A H 0.1816 0.1881 0.1912 0.080 Uiso 1 1 calc R U . . .
C13A C 0.4260(11) 0.1469(3) 0.3209(4) 0.0832(15) Uani 1 1 d . . . . .
H13A H 0.3243 0.1023 0.3279 0.100 Uiso 1 1 calc R U . . .
C14A C 0.6542(10) 0.1614(3) 0.3908(4) 0.0838(15) Uani 1 1 d . . . . .
H14A H 0.7073 0.1272 0.4462 0.101 Uiso 1 1 calc R U . . .
C15A C 0.8068(9) 0.2254(3) 0.3811(3) 0.0782(14) Uani 1 1 d . . . . .
H15A H 0.9636 0.2349 0.4300 0.094 Uiso 1 1 calc R U . . .
C16A C 0.7313(8) 0.2769(3) 0.2989(3) 0.0652(11) Uani 1 1 d . . . . .
H16A H 0.8385 0.3204 0.2920 0.078 Uiso 1 1 calc R U . . .
C21A C 0.5174(6) 0.4180(2) 0.0237(3) 0.0453(8) Uani 1 1 d . . . . .
C22A C 0.3350(7) 0.4770(2) 0.0320(3) 0.0511(9) Uani 1 1 d . . . . .
C23A C 0.2782(8) 0.5326(2) -0.0457(3) 0.0567(10) Uani 1 1 d . . . . .
C24A C 0.3999(9) 0.5316(3) -0.1306(3) 0.0707(12) Uani 1 1 d . . . . .
H24A H 0.3588 0.5691 -0.1829 0.085 Uiso 1 1 calc R U . . .
C25A C 0.5879(9) 0.4731(3) -0.1369(3) 0.0721(12) Uani 1 1 d . . . . .
H25A H 0.6777 0.4720 -0.1936 0.086 Uiso 1 1 calc R U . . .
C26A C 0.6435(7) 0.4171(3) -0.0616(3) 0.0635(11) Uani 1 1 d . . . . .
H26A H 0.7682 0.3778 -0.0681 0.076 Uiso 1 1 calc R U . . .
F22B F 0.5298(4) 0.15691(14) -0.2754(2) 0.0868(8) Uani 1 1 d . . . . .
F23B F 0.4071(6) 0.2621(2) -0.4259(2) 0.1143(11) Uani 1 1 d . . . . .
O1B O 0.5683(5) 0.17478(16) -0.0640(2) 0.0713(8) Uani 1 1 d . . . . .
C1B C 0.7971(7) 0.1476(2) -0.0557(3) 0.0506(9) Uani 1 1 d . . . . .
N1B N 0.9746(6) 0.17333(18) -0.1147(2) 0.0499(8) Uani 1 1 d . . . . .
H1B H 1.128(9) 0.161(2) -0.098(3) 0.070(13) Uiso 1 1 d . . . . .
C11B C 0.8923(6) 0.0823(2) 0.0167(3) 0.0511(9) Uani 1 1 d . . . . .
C12B C 0.7723(7) 0.0735(3) 0.1036(3) 0.0647(11) Uani 1 1 d . . . . .
H12B H 0.6388 0.1084 0.1159 0.078 Uiso 1 1 calc R U . . .
C13B C 0.8512(9) 0.0129(3) 0.1721(4) 0.0752(12) Uani 1 1 d . . . . .
H13B H 0.7729 0.0078 0.2314 0.090 Uiso 1 1 calc R U . . .
C14B C 1.0420(8) -0.0398(3) 0.1542(4) 0.0720(12) Uani 1 1 d . . . . .
H14B H 1.0913 -0.0808 0.2006 0.086 Uiso 1 1 calc R U . . .
C15B C 1.1617(8) -0.0323(2) 0.0679(4) 0.0662(11) Uani 1 1 d . . . . .
H15B H 1.2914 -0.0684 0.0555 0.079 Uiso 1 1 calc R U . . .
C16B C 1.0892(7) 0.0292(2) -0.0010(3) 0.0577(10) Uani 1 1 d . . . . .
H16B H 1.1725 0.0348 -0.0590 0.069 Uiso 1 1 calc R U . . .
C21B C 0.9074(6) 0.2308(2) -0.1950(3) 0.0431(8) Uani 1 1 d . . . . .
C22B C 0.6868(7) 0.2217(2) -0.2726(3) 0.0545(9) Uani 1 1 d . . . . .
C23B C 0.6264(8) 0.2762(3) -0.3518(3) 0.0712(13) Uani 1 1 d . . . . .
C24B C 0.7897(10) 0.3393(3) -0.3556(4) 0.0773(14) Uani 1 1 d . . . . .
H24B H 0.7501 0.3758 -0.4091 0.093 Uiso 1 1 calc R U . . .
C25B C 1.0147(9) 0.3475(3) -0.2786(4) 0.0709(12) Uani 1 1 d . . . . .
H25B H 1.1298 0.3901 -0.2804 0.085 Uiso 1 1 calc R U . . .
C26B C 1.0732(7) 0.2944(2) -0.1989(3) 0.0533(9) Uani 1 1 d . . . . .
H26B H 1.2259 0.3014 -0.1471 0.064 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
F22A C22A 1.333(4) . ?
F23A C23A 1.342(4) . ?
O1A C1A 1.222(4) . ?
C1A N1A 1.352(5) . ?
C1A C11A 1.484(5) . ?
N1A C21A 1.422(5) . ?
N1A H1A 0.81(5) . ?
C11A C12A 1.379(5) . ?
C11A C16A 1.391(5) . ?
C12A C13A 1.389(6) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.348(7) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.352(7) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.384(6) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21A C26A 1.372(5) . ?
C21A C22A 1.376(5) . ?
C22A C23A 1.379(5) . ?
C23A C24A 1.354(5) . ?
C24A C25A 1.385(6) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.363(6) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
F22B C22B 1.354(4) . ?
F23B C23B 1.346(5) . ?
O1B C1B 1.220(4) . ?
C1B N1B 1.348(4) . ?
C1B C11B 1.484(5) . ?
N1B C21B 1.430(4) . ?
N1B H1B 0.79(5) . ?
C11B C12B 1.382(5) . ?
C11B C16B 1.388(5) . ?
C12B C13B 1.378(6) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.362(6) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.371(6) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.386(5) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21B C22B 1.362(5) . ?
C21B C26B 1.372(5) . ?
C22B C23B 1.382(6) . ?
C23B C24B 1.358(6) . ?
C24B C25B 1.372(7) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.371(6) . ?
C25B H25B 0.9300 . ?
C26B H26B 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
O1A C1A N1A 122.0(3) . . ?
O1A C1A C11A 121.8(3) . . ?
N1A C1A C11A 116.2(3) . . ?
C1A N1A C21A 123.0(3) . . ?
C1A N1A H1A 119(3) . . ?
C21A N1A H1A 117(3) . . ?
C12A C11A C16A 118.9(4) . . ?
C12A C11A C1A 118.0(3) . . ?
C16A C11A C1A 123.0(3) . . ?
C11A C12A C13A 119.7(4) . . ?
C11A C12A H12A 120.1 . . ?
C13A C12A H12A 120.1 . . ?
C14A C13A C12A 120.6(5) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C13A C14A C15A 120.6(5) . . ?
C13A C14A H14A 119.7 . . ?
C15A C14A H14A 119.7 . . ?
C14A C15A C16A 120.5(4) . . ?
C14A C15A H15A 119.7 . . ?
C16A C15A H15A 119.7 . . ?
C15A C16A C11A 119.7(4) . . ?
C15A C16A H16A 120.2 . . ?
C11A C16A H16A 120.2 . . ?
C26A C21A C22A 118.6(3) . . ?
C26A C21A N1A 120.8(3) . . ?
C22A C21A N1A 120.5(3) . . ?
F22A C22A C21A 121.4(3) . . ?
F22A C22A C23A 118.6(3) . . ?
C21A C22A C23A 120.0(3) . . ?
F23A C23A C24A 120.2(4) . . ?
F23A C23A C22A 118.0(4) . . ?
C24A C23A C22A 121.8(4) . . ?
C23A C24A C25A 117.8(4) . . ?
C23A C24A H24A 121.1 . . ?
C25A C24A H24A 121.1 . . ?
C26A C25A C24A 121.2(4) . . ?
C26A C25A H25A 119.4 . . ?
C24A C25A H25A 119.4 . . ?
C25A C26A C21A 120.6(4) . . ?
C25A C26A H26A 119.7 . . ?
C21A C26A H26A 119.7 . . ?
O1B C1B N1B 121.8(3) . . ?
O1B C1B C11B 122.1(3) . . ?
N1B C1B C11B 116.1(3) . . ?
C1B N1B C21B 123.3(3) . . ?
C1B N1B H1B 118(3) . . ?
C21B N1B H1B 118(3) . . ?
C12B C11B C16B 119.3(4) . . ?
C12B C11B C1B 117.7(3) . . ?
C16B C11B C1B 122.9(3) . . ?
C13B C12B C11B 119.7(4) . . ?
C13B C12B H12B 120.1 . . ?
C11B C12B H12B 120.1 . . ?
C14B C13B C12B 121.0(4) . . ?
C14B C13B H13B 119.5 . . ?
C12B C13B H13B 119.5 . . ?
C13B C14B C15B 120.1(4) . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C14B C15B C16B 120.0(4) . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B C11B 120.0(4) . . ?
C15B C16B H16B 120.0 . . ?
C11B C16B H16B 120.0 . . ?
C22B C21B C26B 118.5(3) . . ?
C22B C21B N1B 121.0(3) . . ?
C26B C21B N1B 120.5(3) . . ?
F22B C22B C21B 120.1(4) . . ?
F22B C22B C23B 119.0(4) . . ?
C21B C22B C23B 120.9(4) . . ?
F23B C23B C24B 122.2(4) . . ?
F23B C23B C22B 117.0(4) . . ?
C24B C23B C22B 120.8(4) . . ?
C23B C24B C25B 118.2(4) . . ?
C23B C24B H24B 120.9 . . ?
C25B C24B H24B 120.9 . . ?
C26B C25B C24B 121.3(4) . . ?
C26B C25B H25B 119.4 . . ?
C24B C25B H25B 119.4 . . ?
C25B C26B C21B 120.3(4) . . ?
C25B C26B H26B 119.8 . . ?
C21B C26B H26B 119.8 . . ?

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
O1A C1A N1A C21A 0.4(5) . . . . ?
C11A C1A N1A C21A -177.8(3) . . . . ?
O1A C1A C11A C12A 26.8(5) . . . . ?
N1A C1A C11A C12A -154.9(3) . . . . ?
O1A C1A C11A C16A -151.1(4) . . . . ?
N1A C1A C11A C16A 27.1(5) . . . . ?
C16A C11A C12A C13A -0.3(6) . . . . ?
C1A C11A C12A C13A -178.4(4) . . . . ?
C11A C12A C13A C14A 1.2(7) . . . . ?
C12A C13A C14A C15A -0.9(7) . . . . ?
C13A C14A C15A C16A -0.2(7) . . . . ?
C14A C15A C16A C11A 1.0(7) . . . . ?
C12A C11A C16A C15A -0.8(6) . . . . ?
C1A C11A C16A C15A 177.2(4) . . . . ?
C1A N1A C21A C26A -127.6(4) . . . . ?
C1A N1A C21A C22A 55.4(5) . . . . ?
C26A C21A C22A F22A -176.5(3) . . . . ?
N1A C21A C22A F22A 0.5(5) . . . . ?
C26A C21A C22A C23A 1.3(5) . . . . ?
N1A C21A C22A C23A 178.4(3) . . . . ?
F22A C22A C23A F23A -2.4(5) . . . . ?
C21A C22A C23A F23A 179.7(3) . . . . ?
F22A C22A C23A C24A 177.2(3) . . . . ?
C21A C22A C23A C24A -0.8(5) . . . . ?
F23A C23A C24A C25A 178.8(3) . . . . ?
C22A C23A C24A C25A -0.7(6) . . . . ?
C23A C24A C25A C26A 1.6(6) . . . . ?
C24A C25A C26A C21A -1.1(6) . . . . ?
C22A C21A C26A C25A -0.4(6) . . . . ?
N1A C21A C26A C25A -177.5(4) . . . . ?
O1B C1B N1B C21B -3.4(5) . . . . ?
C11B C1B N1B C21B 174.1(3) . . . . ?
O1B C1B C11B C12B -26.6(5) . . . . ?
N1B C1B C11B C12B 155.9(3) . . . . ?
O1B C1B C11B C16B 151.6(4) . . . . ?
N1B C1B C11B C16B -25.9(5) . . . . ?
C16B C11B C12B C13B 0.7(6) . . . . ?
C1B C11B C12B C13B 179.0(4) . . . . ?
C11B C12B C13B C14B -1.4(7) . . . . ?
C12B C13B C14B C15B 0.9(7) . . . . ?
C13B C14B C15B C16B 0.3(7) . . . . ?
C14B C15B C16B C11B -1.1(6) . . . . ?
C12B C11B C16B C15B 0.6(5) . . . . ?
C1B C11B C16B C15B -177.6(3) . . . . ?
C1B N1B C21B C22B -53.6(5) . . . . ?
C1B N1B C21B C26B 130.1(4) . . . . ?
C26B C21B C22B F22B 175.3(3) . . . . ?
N1B C21B C22B F22B -1.1(5) . . . . ?
C26B C21B C22B C23B -1.8(5) . . . . ?
N1B C21B C22B C23B -178.2(3) . . . . ?
F22B C22B C23B F23B 2.0(5) . . . . ?
C21B C22B C23B F23B 179.1(3) . . . . ?
F22B C22B C23B C24B -175.4(3) . . . . ?
C21B C22B C23B C24B 1.7(6) . . . . ?
F23B C23B C24B C25B -177.7(4) . . . . ?
C22B C23B C24B C25B -0.4(6) . . . . ?
C23B C24B C25B C26B -0.7(6) . . . . ?
C24B C25B C26B C21B 0.5(6) . . . . ?
C22B C21B C26B C25B 0.7(5) . . . . ?
N1B C21B C26B C25B 177.1(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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A O1A 0.81(5) 2.15(5) 2.914(4) 158(4) 1_655 yes
N1B H1B O1B 0.79(5) 2.18(5) 2.920(4) 157(4) 1_655 yes
C14B H14B F22B 0.93 2.52 3.160(5) 126 2_655 yes
#   C25B H25B F22A  0.93      2.63      3.432(4)  145       2_664  yes
#   C12B H12B C12A  0.93      2.82      3.689(6)  156       .      no
#   C26A H26A C26B  0.93      2.86      3.686(5)  148       .      no

#   Contact data for C-H...F and C-H...C interactions.
#
#    Crystals grown from CH2Cl2

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_23_F2_294K
_database_code_depnum_ccdc_archive 'CCDC 1453271'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(23_F2 or 10-015)'
_chemical_name_common            ?
_chemical_melting_point          377
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   5.2115(2)
_cell_length_b                   6.4193(3)
_cell_length_c                   16.1911(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.894(4)
_cell_angle_gamma                90
_cell_volume                     536.53(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2054
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.985

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'Empirical - ABSPACK'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            3561
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.419
_diffrn_reflns_theta_max         27.334
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_point_group_measured_fraction_full 0.791
_reflns_number_total             1810
_reflns_number_gt                1466
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.552
_reflns_Friedel_fraction_max     0.531
_reflns_Friedel_fraction_full    0.582

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/6 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0665P)²+0.0116P] 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_abs_structure_details 
;
Flack x from 445 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.4(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1810
_refine_ls_number_parameters     158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030

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
F12 F 0.8744(4) 0.6872(3) 0.16863(15) 0.0715(6) Uani 1 1 d . . . . .
F13 F 1.0045(5) 0.3828(4) 0.27550(17) 0.0936(8) Uani 1 1 d . . . . .
O1 O 0.1873(4) 0.6931(4) 0.02035(19) 0.0698(7) Uani 1 1 d . . . . .
N1 N 0.6027(5) 0.7736(4) 0.00920(18) 0.0486(6) Uani 1 1 d . . . . .
H1 H 0.789(8) 0.745(5) 0.029(2) 0.059(9) Uiso 1 1 d . . . . .
C1 C 0.4212(5) 0.6646(5) 0.0407(2) 0.0482(7) Uani 1 1 d . . . . .
C11 C 0.5101(6) 0.4980(4) 0.10206(19) 0.0479(7) Uani 1 1 d . . . . .
C12 C 0.7285(6) 0.5137(5) 0.1616(2) 0.0509(7) Uani 1 1 d . . . . .
C13 C 0.7952(7) 0.3552(6) 0.2177(2) 0.0623(9) Uani 1 1 d . . . . .
C14 C 0.6530(8) 0.1778(6) 0.2163(3) 0.0706(10) Uani 1 1 d . . . . .
H14 H 0.7018 0.0709 0.2539 0.085 Uiso 1 1 calc R U . . .
C15 C 0.4365(9) 0.1591(6) 0.1586(3) 0.0753(11) Uani 1 1 d . . . . .
H15 H 0.3369 0.0385 0.1571 0.090 Uiso 1 1 calc R U . . .
C16 C 0.3642(8) 0.3176(5) 0.1023(3) 0.0656(9) Uani 1 1 d . . . . .
H16 H 0.2152 0.3028 0.0640 0.079 Uiso 1 1 calc R U . . .
C21 C 0.5626(5) 0.9506(4) -0.04435(18) 0.0468(7) Uani 1 1 d . . . . .
C22 C 0.3440(6) 0.9750(6) -0.1014(2) 0.0589(8) Uani 1 1 d . . . . .
H22 H 0.2165 0.8726 -0.1078 0.071 Uiso 1 1 calc R U . . .
C23 C 0.3166(7) 1.1562(6) -0.1495(2) 0.0698(10) Uani 1 1 d . . . . .
H23 H 0.1685 1.1750 -0.1879 0.084 Uiso 1 1 calc R U . . .
C24 C 0.5036(8) 1.3055(7) -0.1410(3) 0.0721(11) Uani 1 1 d . . . . .
H24 H 0.4815 1.4263 -0.1729 0.087 Uiso 1 1 calc R U . . .
C25 C 0.7254(8) 1.2784(6) -0.0852(3) 0.0711(11) Uani 1 1 d . . . . .
H25 H 0.8551 1.3790 -0.0799 0.085 Uiso 1 1 calc R U . . .
C26 C 0.7528(7) 1.0997(5) -0.0372(2) 0.0612(9) Uani 1 1 d . . . . .
H26 H 0.9024 1.0802 0.0004 0.073 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
F12 C12 1.344(4) . ?
F13 C13 1.348(4) . ?
O1 C1 1.232(4) . ?
N1 C1 1.333(4) . ?
N1 C21 1.427(4) . ?
N1 H1 1.00(4) . ?
C1 C11 1.490(4) . ?
C11 C16 1.386(5) . ?
C11 C12 1.391(4) . ?
C12 C13 1.377(5) . ?
C13 C14 1.357(6) . ?
C14 C15 1.368(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.371(4) . ?
C21 C22 1.373(4) . ?
C22 C23 1.397(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 N1 C21 126.7(2) . . ?
C1 N1 H1 119(2) . . ?
C21 N1 H1 114(2) . . ?
O1 C1 N1 123.3(3) . . ?
O1 C1 C11 119.4(3) . . ?
N1 C1 C11 117.4(3) . . ?
C16 C11 C12 117.1(3) . . ?
C16 C11 C1 118.8(3) . . ?
C12 C11 C1 124.1(2) . . ?
F12 C12 C13 117.9(3) . . ?
F12 C12 C11 121.3(3) . . ?
C13 C12 C11 120.8(3) . . ?
F13 C13 C14 120.6(3) . . ?
F13 C13 C12 117.9(3) . . ?
C14 C13 C12 121.5(3) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.1(4) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C26 C21 C22 120.0(3) . . ?
C26 C21 N1 117.4(3) . . ?
C22 C21 N1 122.6(3) . . ?
C21 C22 C23 118.8(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 119.1(4) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C21 C26 C25 121.0(4) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?

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
C21 N1 C1 O1 7.2(5) . . . . ?
C21 N1 C1 C11 -174.1(3) . . . . ?
O1 C1 C11 C16 33.9(5) . . . . ?
N1 C1 C11 C16 -144.9(3) . . . . ?
O1 C1 C11 C12 -144.2(3) . . . . ?
N1 C1 C11 C12 37.0(4) . . . . ?
C16 C11 C12 F12 -176.7(3) . . . . ?
C1 C11 C12 F12 1.4(4) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C1 C11 C12 C13 178.4(3) . . . . ?
F12 C12 C13 F13 -0.8(4) . . . . ?
C11 C12 C13 F13 -177.9(3) . . . . ?
F12 C12 C13 C14 177.9(3) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
F13 C13 C14 C15 177.6(4) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C11 0.8(6) . . . . ?
C12 C11 C16 C15 -1.1(5) . . . . ?
C1 C11 C16 C15 -179.3(3) . . . . ?
C1 N1 C21 C26 147.8(3) . . . . ?
C1 N1 C21 C22 -32.3(5) . . . . ?
C26 C21 C22 C23 -2.0(5) . . . . ?
N1 C21 C22 C23 178.0(3) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C25 0.9(6) . . . . ?
C23 C24 C25 C26 -1.2(6) . . . . ?
C22 C21 C26 C25 1.8(5) . . . . ?
N1 C21 C26 C25 -178.2(3) . . . . ?
C24 C25 C26 C21 -0.2(5) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 O1 1.00(4) 2.13(4) 3.071(3) 157(3) 1_655 yes
N1 H1 F12 1.00(4) 2.27(4) 2.823(4) 114(3) . yes
C22 H22 O1 0.93 2.40 2.875(4) 112 . yes
#   C22  H22  F13   0.93      2.63      3.378(4)  138       2_464  yes

#   Contact data for C-H...F interaction.
#
#    Crystals grown from n-hexane

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_F2_24_294K
_database_code_depnum_ccdc_archive 'CCDC 1453272'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(F2_24 or 11-051)'
_chemical_name_common            ?
_chemical_melting_point          395
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   5.5268(3)
_cell_length_b                   4.9905(2)
_cell_length_c                   19.7058(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.665(5)
_cell_angle_gamma                90
_cell_volume                     543.48(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1059
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      27.96

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            6736
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.083
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2370
_reflns_number_gt                1051
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.909
_reflns_Friedel_fraction_full    0.997

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_refine_special_details          
'Twin, Disordered components treated accordingly'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x from 394 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.9(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     209
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   0.767
_refine_ls_restrained_S_all      0.767
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.075
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.020

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
O1 O 0.5068(6) 1.1266(5) 0.17874(18) 0.0741(10) Uani 0.88 1 d . . P A 1
C1 C 0.5672(8) 0.8901(9) 0.1738(3) 0.0570(13) Uani 0.88 1 d . . P A 1
N1 N 0.4895(7) 0.7000(8) 0.2142(2) 0.0524(12) Uani 0.88 1 d . . P A 1
H1 H 0.5374 0.5385 0.2071 0.09(2) Uiso 1 1 calc R . . A 1
C11 C 0.7509(7) 0.8014(8) 0.1198(2) 0.0624(12) Uani 1 1 d . . . A 1
C12 C 0.7583(8) 0.9462(9) 0.0625(2) 0.0736(14) Uani 1 1 d . . . A 1
H12 H 0.6451 1.0817 0.0556 0.088 Uiso 1 1 calc R U . A 1
C13 C 0.9247(9) 0.9007(10) 0.0147(2) 0.0793(15) Uani 1 1 d . . . A 1
H13 H 0.9255 1.0051 -0.0244 0.095 Uiso 1 1 calc R U . A 1
C14 C 1.0929(9) 0.7020(10) 0.0231(2) 0.0803(14) Uani 1 1 d . . . A 1
H14 H 1.2098 0.6716 -0.0096 0.096 Uiso 0.88 1 calc R U P A 1
C15 C 1.0853(8) 0.5468(8) 0.0816(3) 0.0794(17) Uani 1 1 d . . . A 1
H15 H 1.1974 0.4103 0.0885 0.095 Uiso 1 1 calc R U . A 1
C16 C 0.9099(8) 0.5970(8) 0.1292(2) 0.0691(13) Uani 1 1 d . . . A 1
H16 H 0.9006 0.4906 0.1678 0.083 Uiso 0.88 1 calc R U P A 1
C21 C 0.3316(7) 0.7470(8) 0.2687(2) 0.0531(12) Uani 1 1 d . . . A 1
C22 C 0.3521(7) 0.5840(9) 0.3247(2) 0.0592(12) Uani 1 1 d . . . A 1
H22 H 0.4760 0.4580 0.3260 0.071 Uiso 0.18 1 calc R U P A 1
C23 C 0.1989(9) 0.5988(9) 0.3783(2) 0.0723(13) Uani 1 1 d . . . A 1
H23 H 0.2179 0.4873 0.4158 0.087 Uiso 1 1 calc R U . A 1
C24 C 0.0176(8) 0.7822(9) 0.3750(3) 0.0742(15) Uani 1 1 d . . . A 1
H24 H -0.0884 0.7953 0.4111 0.089 Uiso 0.12 1 calc R U P A 1
C25 C -0.0144(8) 0.9463(8) 0.3210(3) 0.0691(15) Uani 1 1 d . . . A 1
H25 H -0.1412 1.0687 0.3200 0.083 Uiso 1 1 calc R U . A 1
C26 C 0.1434(7) 0.9297(8) 0.2676(2) 0.0630(12) Uani 1 1 d . . . A 1
H26 H 0.1233 1.0426 0.2305 0.076 Uiso 0.94 1 calc R U P A 1
F22 F 0.5313(4) 0.4021(5) 0.32878(14) 0.0795(9) Uani 0.82 1 d . . P B 2
F24 F -0.1369(5) 0.8031(6) 0.42853(16) 0.1065(12) Uani 0.88 1 d . . P C 2
F14B F 1.248(5) 0.732(5) -0.0337(13) 0.138(10) Uani 0.12 1 d . U P D 2
F16B F 0.995(5) 0.383(4) 0.1775(14) 0.123(8) Uani 0.12 1 d . U P E 2
F26B F 0.137(7) 1.092(7) 0.2187(18) 0.064(9) Uani 0.06 1 d . U P F 2
O1B O 0.626(5) 0.367(5) 0.2109(14) 0.091(7) Uani 0.12 1 d . U P A 2
C1B C 0.483(11) 0.838(11) 0.219(3) 0.081(9) Uani 0.12 1 d . U P A 2
N1B N 0.625(6) 0.621(7) 0.1792(17) 0.084(7) Uani 0.12 1 d . U P A 2


_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
O1 C1 1.231(5) . ?
C1 N1 1.314(6) . ?
C1 C11 1.544(6) . ?
N1 C21 1.411(6) . ?
N1 H1 0.8600 . ?
C11 C12 1.343(5) . ?
C11 C16 1.357(5) . ?
C12 C13 1.343(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C1B 1.37(7) . ?
C21 C22 1.374(5) . ?
C21 C26 1.383(5) . ?
C22 C23 1.364(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.358(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.352(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O1B N1B 1.41(4) . ?
C1B N1B 1.56(5) . ?

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 123.6(5) . . ?
O1 C1 C11 120.7(4) . . ?
N1 C1 C11 115.6(4) . . ?
C1 N1 C21 123.4(4) . . ?
C1 N1 H1 118.3 . . ?
C21 N1 H1 118.3 . . ?
C12 C11 C16 119.5(4) . . ?
C12 C11 C1 116.9(4) . . ?
C16 C11 C1 123.5(4) . . ?
C11 C12 C13 121.8(4) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 118.5(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 119.4(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C11 C16 C15 120.2(4) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C22 C21 C26 117.2(4) . . ?
C22 C21 N1 117.8(4) . . ?
C26 C21 N1 124.8(4) . . ?
C23 C22 C21 122.9(4) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C24 C23 C22 117.6(5) . . ?
C24 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
C25 C24 C23 122.4(5) . . ?
C25 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
C24 C25 C26 119.1(4) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 120.7(4) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
O1B N1B C1B 114(4) . . ?

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
O1 C1 N1 C21 -1.3(6) . . . . ?
C11 C1 N1 C21 176.5(4) . . . . ?
O1 C1 C11 C12 -29.1(6) . . . . ?
N1 C1 C11 C12 153.0(4) . . . . ?
O1 C1 C11 C16 147.4(4) . . . . ?
N1 C1 C11 C16 -30.5(6) . . . . ?
C16 C11 C12 C13 -2.4(7) . . . . ?
C1 C11 C12 C13 174.3(4) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C12 C11 C16 C15 3.1(6) . . . . ?
C1 C11 C16 C15 -173.3(4) . . . . ?
C14 C15 C16 C11 -1.9(6) . . . . ?
C1 N1 C21 C22 -148.9(4) . . . . ?
C1 N1 C21 C26 37.0(6) . . . . ?
C26 C21 C22 C23 -0.9(6) . . . . ?
N1 C21 C22 C23 -175.4(4) . . . . ?
C21 C22 C23 C24 0.7(7) . . . . ?
C22 C23 C24 C25 0.1(7) . . . . ?
C23 C24 C25 C26 -0.6(7) . . . . ?
C24 C25 C26 C21 0.4(6) . . . . ?
C22 C21 C26 C25 0.4(6) . . . . ?
N1 C21 C26 C25 174.5(4) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 O1 0.86 2.14 2.948(5) 157 1_545 yes
C26 H26 O1 0.93 2.40 2.854(5) 110 . yes
C25 H25 F22 0.93 2.47 3.393(5) 175 1_465 yes

#
#    Crystals grown from CH2Cl2

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_24_F2_294K
_database_code_depnum_ccdc_archive 'CCDC 1453273'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(24-F2 or 10-016)'
_chemical_name_common            ?
_chemical_melting_point          396
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.4250(2)
_cell_length_b                   7.7256(3)
_cell_length_c                   25.4216(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.708(3)
_cell_angle_gamma                90
_cell_volume                     1064.26(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1102
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      27.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            7313
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.571
_diffrn_reflns_theta_max         27.038
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2297
_reflns_number_gt                1038
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_refine_special_details          
;
Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)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         2297
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_restrained_S_all      0.837
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.060

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
F12 F -0.2735(2) 0.6217(2) 0.20650(5) 0.0624(4) Uani 1 1 d . . . . .
F14 F -0.0210(3) 0.7760(2) 0.04061(6) 0.0778(5) Uani 1 1 d . . . . .
O1 O 0.3659(3) 0.8176(3) 0.27566(7) 0.0703(6) Uani 1 1 d . . . . .
N1 N -0.0342(4) 0.7720(3) 0.29216(8) 0.0425(5) Uani 1 1 d . . . . .
H1 H -0.165(4) 0.757(3) 0.2782(9) 0.041(8) Uiso 1 1 d . . . . .
C1 C 0.1518(4) 0.7921(3) 0.25966(9) 0.0445(6) Uani 1 1 d . . . . .
C11 C 0.0903(4) 0.7867(3) 0.20156(8) 0.0395(6) Uani 1 1 d . . . . .
C12 C -0.1087(4) 0.7031(3) 0.17691(9) 0.0419(6) Uani 1 1 d . . . . .
C13 C -0.1493(4) 0.6963(3) 0.12343(9) 0.0491(6) Uani 1 1 d . . . . .
H13 H -0.2839 0.6374 0.1081 0.059 Uiso 1 1 calc R U . . .
C14 C 0.0159(4) 0.7797(4) 0.09353(9) 0.0509(6) Uani 1 1 d . . . . .
C15 C 0.2176(4) 0.8658(4) 0.11485(10) 0.0524(7) Uani 1 1 d . . . . .
H15 H 0.3272 0.9219 0.0935 0.063 Uiso 1 1 calc R U . . .
C16 C 0.2525(4) 0.8667(3) 0.16856(10) 0.0476(6) Uani 1 1 d . . . . .
H16 H 0.3901 0.9231 0.1835 0.057 Uiso 1 1 calc R U . . .
C21 C -0.0258(4) 0.7771(3) 0.34771(9) 0.0395(5) Uani 1 1 d . . . . .
C22 C 0.1622(4) 0.8580(3) 0.37722(9) 0.0495(6) Uani 1 1 d . . . . .
H22 H 0.2918 0.9105 0.3606 0.059 Uiso 1 1 calc R U . . .
C23 C 0.1560(4) 0.8601(4) 0.43140(10) 0.0567(7) Uani 1 1 d . . . . .
H23 H 0.2820 0.9147 0.4511 0.068 Uiso 1 1 calc R U . . .
C24 C -0.0335(5) 0.7828(4) 0.45672(10) 0.0600(7) Uani 1 1 d . . . . .
H24 H -0.0357 0.7844 0.4933 0.072 Uiso 1 1 calc R U . . .
C25 C -0.2194(4) 0.7031(4) 0.42725(10) 0.0582(7) Uani 1 1 d . . . . .
H25 H -0.3484 0.6505 0.4441 0.070 Uiso 1 1 calc R U . . .
C26 C -0.2173(4) 0.7001(3) 0.37312(10) 0.0494(6) Uani 1 1 d . . . . .
H26 H -0.3447 0.6462 0.3536 0.059 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
F12 C12 1.350(2) . ?
F14 C14 1.351(3) . ?
O1 C1 1.228(3) . ?
N1 C1 1.343(3) . ?
N1 C21 1.411(3) . ?
N1 H1 0.79(2) . ?
C1 C11 1.499(3) . ?
C11 C12 1.383(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.368(3) . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(4) . ?
C15 C16 1.370(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.383(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.374(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 N1 C21 128.5(2) . . ?
C1 N1 H1 115.4(16) . . ?
C21 N1 H1 116.1(16) . . ?
O1 C1 N1 122.8(2) . . ?
O1 C1 C11 119.6(2) . . ?
N1 C1 C11 117.7(2) . . ?
C12 C11 C16 115.9(2) . . ?
C12 C11 C1 126.3(2) . . ?
C16 C11 C1 117.7(2) . . ?
F12 C12 C13 117.1(2) . . ?
F12 C12 C11 119.2(2) . . ?
C13 C12 C11 123.6(2) . . ?
C14 C13 C12 117.2(2) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
F14 C14 C13 118.3(2) . . ?
F14 C14 C15 118.8(2) . . ?
C13 C14 C15 122.9(2) . . ?
C16 C15 C14 117.8(2) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C11 122.6(2) . . ?
C15 C16 H16 118.7 . . ?
C11 C16 H16 118.7 . . ?
C26 C21 C22 119.4(2) . . ?
C26 C21 N1 117.8(2) . . ?
C22 C21 N1 122.9(2) . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 120.8(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 120.1(2) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?

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
C21 N1 C1 O1 0.7(4) . . . . ?
C21 N1 C1 C11 -178.0(2) . . . . ?
O1 C1 C11 C12 155.7(2) . . . . ?
N1 C1 C11 C12 -25.6(4) . . . . ?
O1 C1 C11 C16 -21.5(4) . . . . ?
N1 C1 C11 C16 157.2(2) . . . . ?
C16 C11 C12 F12 179.7(2) . . . . ?
C1 C11 C12 F12 2.4(4) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
C1 C11 C12 C13 -177.0(3) . . . . ?
F12 C12 C13 C14 179.5(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 F14 -179.6(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
F14 C14 C15 C16 -179.4(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C11 -1.0(4) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
C1 C11 C16 C15 178.4(2) . . . . ?
C1 N1 C21 C26 -159.8(2) . . . . ?
C1 N1 C21 C22 21.4(4) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
N1 C21 C22 C23 179.0(2) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
C22 C21 C26 C25 -0.4(4) . . . . ?
N1 C21 C26 C25 -179.3(2) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 O1 0.79(2) 2.58(2) 3.281(3) 148(2) 1_455 yes
N1 H1 F12 0.79(2) 2.16(2) 2.740(2) 131(2) . yes
C22 H22 O1 0.93 2.33 2.873(3) 117 . yes

#
#    Crystals grown from n-hexane

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_F2_25_294K
_database_code_depnum_ccdc_archive 'CCDC 1453274'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(F2_25 or 11-034)'
_chemical_name_common            ?
_chemical_melting_point          388
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   24.4897(16)
_cell_length_b                   5.0316(3)
_cell_length_c                   8.6187(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1062.02(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    221
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.70

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            5645
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         26.969
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             2078
_reflns_number_gt                1819
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.806
_reflns_Friedel_fraction_full    0.831

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0988P)²+0.2560P] 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_abs_structure_details 
;
Flack x from 635 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   1.7(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1675
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.068

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
F22 F 0.25190(13) -0.0863(5) 1.0999(4) 0.0621(8) Uani 1 1 d . . . . .
F25 F 0.13901(11) 0.6203(6) 0.7542(4) 0.0711(10) Uani 1 1 d . . . . .
O1 O 0.33291(12) 0.6557(5) 0.8533(5) 0.0553(9) Uani 1 1 d . . . . .
C1 C 0.34613(17) 0.4287(7) 0.8842(5) 0.0407(9) Uani 1 1 d . . . . .
N1 N 0.30956(13) 0.2334(7) 0.9152(5) 0.0446(8) Uani 1 1 d . . . . .
H1 H 0.321(2) 0.060(12) 0.933(8) 0.066(16) Uiso 1 1 d . . . . .
C11 C 0.40479(16) 0.3456(7) 0.8929(5) 0.0411(9) Uani 1 1 d . . . . .
C12 C 0.44202(18) 0.4886(9) 0.8037(6) 0.0497(10) Uani 1 1 d . . . . .
H12 H 0.4298 0.6279 0.7419 0.060 Uiso 1 1 calc R U . . .
C13 C 0.49688(19) 0.4255(9) 0.8064(7) 0.0589(12) Uani 1 1 d . . . . .
H13 H 0.5214 0.5203 0.7455 0.071 Uiso 1 1 calc R U . . .
C14 C 0.51521(18) 0.2218(10) 0.8996(7) 0.0590(12) Uani 1 1 d . . . . .
H14 H 0.5521 0.1789 0.9017 0.071 Uiso 1 1 calc R U . . .
C15 C 0.4789(2) 0.0822(10) 0.9891(7) 0.0594(13) Uani 1 1 d . . . . .
H15 H 0.4915 -0.0545 1.0522 0.071 Uiso 1 1 calc R U . . .
C16 C 0.42378(18) 0.1416(8) 0.9870(6) 0.0506(10) Uani 1 1 d . . . . .
H16 H 0.3996 0.0455 1.0483 0.061 Uiso 1 1 calc R U . . .
C21 C 0.25240(15) 0.2619(7) 0.9195(5) 0.0379(8) Uani 1 1 d . . . . .
C22 C 0.22304(18) 0.0913(8) 1.0151(5) 0.0435(9) Uani 1 1 d . . . . .
C23 C 0.1675(2) 0.0966(9) 1.0258(7) 0.0561(12) Uani 1 1 d . . . . .
H23 H 0.1494 -0.0206 1.0915 0.067 Uiso 1 1 calc R U . . .
C24 C 0.13866(17) 0.2768(10) 0.9387(7) 0.0558(12) Uani 1 1 d . . . . .
H24 H 0.1008 0.2853 0.9447 0.067 Uiso 1 1 calc R U . . .
C25 C 0.16726(18) 0.4443(8) 0.8424(6) 0.0484(10) Uani 1 1 d . . . . .
C26 C 0.22336(17) 0.4436(8) 0.8315(6) 0.0447(9) Uani 1 1 d . . . . .
H26 H 0.2413 0.5626 0.7666 0.054 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
F22 C22 1.354(5) . ?
F25 C25 1.357(5) . ?
O1 C1 1.216(4) . ?
C1 N1 1.356(5) . ?
C1 C11 1.498(5) . ?
N1 C21 1.407(5) . ?
N1 H1 0.93(6) . ?
C11 C16 1.389(6) . ?
C11 C12 1.393(6) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.384(6) . ?
C21 C22 1.391(5) . ?
C22 C23 1.363(6) . ?
C23 C24 1.373(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(6) . ?
C26 H26 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
O1 C1 N1 123.2(4) . . ?
O1 C1 C11 121.9(3) . . ?
N1 C1 C11 114.9(3) . . ?
C1 N1 C21 126.0(3) . . ?
C1 N1 H1 121(3) . . ?
C21 N1 H1 113(3) . . ?
C16 C11 C12 119.0(4) . . ?
C16 C11 C1 123.8(4) . . ?
C12 C11 C1 117.1(4) . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C26 C21 C22 117.8(4) . . ?
C26 C21 N1 124.3(4) . . ?
C22 C21 N1 117.8(4) . . ?
F22 C22 C23 119.8(4) . . ?
F22 C22 C21 117.2(4) . . ?
C23 C22 C21 122.9(4) . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 118.2(4) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
F25 C25 C24 118.6(4) . . ?
F25 C25 C26 118.2(4) . . ?
C24 C25 C26 123.2(4) . . ?
C25 C26 C21 118.5(4) . . ?
C25 C26 H26 120.8 . . ?
C21 C26 H26 120.8 . . ?

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
O1 C1 N1 C21 -1.3(7) . . . . ?
C11 C1 N1 C21 177.9(4) . . . . ?
O1 C1 C11 C16 151.0(5) . . . . ?
N1 C1 C11 C16 -28.2(6) . . . . ?
O1 C1 C11 C12 -27.1(7) . . . . ?
N1 C1 C11 C12 153.6(4) . . . . ?
C16 C11 C12 C13 1.3(7) . . . . ?
C1 C11 C12 C13 179.5(4) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C13 C14 C15 C16 0.4(9) . . . . ?
C14 C15 C16 C11 0.0(8) . . . . ?
C12 C11 C16 C15 -0.8(7) . . . . ?
C1 C11 C16 C15 -178.9(5) . . . . ?
C1 N1 C21 C26 30.0(7) . . . . ?
C1 N1 C21 C22 -151.9(4) . . . . ?
C26 C21 C22 F22 179.7(4) . . . . ?
N1 C21 C22 F22 1.4(6) . . . . ?
C26 C21 C22 C23 -0.2(7) . . . . ?
N1 C21 C22 C23 -178.5(4) . . . . ?
F22 C22 C23 C24 -179.7(4) . . . . ?
C21 C22 C23 C24 0.2(7) . . . . ?
C22 C23 C24 C25 0.6(8) . . . . ?
C23 C24 C25 F25 179.1(4) . . . . ?
C23 C24 C25 C26 -1.4(8) . . . . ?
F25 C25 C26 C21 -179.1(4) . . . . ?
C24 C25 C26 C21 1.4(7) . . . . ?
C22 C21 C26 C25 -0.5(6) . . . . ?
N1 C21 C26 C25 177.6(4) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 O1 0.93(6) 2.17(6) 3.010(4) 151(6) 1_545 yes
C26 H26 O1 0.93 2.41 2.893(5) 112 . yes
C26 H26 F22 0.93 2.28 3.153(5) 156 4_564 yes

#   The C-H...F interaction is a short interaction.
#
#    Crystals grown from CHCl3

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_25_F2_294K
_database_code_depnum_ccdc_archive 'CCDC 1453275'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(25_F2 or 10-017)'
_chemical_name_common            ?
_chemical_melting_point          380
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   5.1850(8)
_cell_length_b                   24.767(4)
_cell_length_c                   8.3089(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.206(17)
_cell_angle_gamma                90
_cell_volume                     1067.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      27.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'Empirical - ABSPACK'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            7448
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.290
_diffrn_reflns_theta_max         27.205
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3629
_reflns_number_gt                1816
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.951

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_refine_special_details          
'Twin, Disordered components treated accordingly'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²] 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-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.0061(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
Flack x from 487 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -2.8(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3629
_refine_ls_number_parameters     384
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_restrained_S_all      0.812
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035

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
F12A F 0.9050(9) 0.47810(18) -0.1396(6) 0.0499(13) Uani 1 1 d . . . . .
F15A F 0.3037(11) 0.61623(16) 0.1943(7) 0.0658(16) Uani 1 1 d . . . . .
O1A O 0.2660(10) 0.4184(2) 0.0964(8) 0.0522(16) Uani 1 1 d . . . . .
N1A N 0.6729(12) 0.3969(3) 0.0281(9) 0.058(3) Uani 1 1 d . . . . .
H1A H 0.8236 0.4104 0.0122 0.070 Uiso 1 1 calc R U . . .
C1A C 0.4823(16) 0.4315(3) 0.0587(10) 0.0343(18) Uani 1 1 d . . . . .
C11A C 0.5567(13) 0.4897(3) 0.0359(9) 0.038(2) Uani 1 1 d . . . . .
C12A C 0.7495(13) 0.5120(3) -0.0546(9) 0.0365(17) Uani 1 1 d . . . . .
C13A C 0.7876(17) 0.5665(3) -0.0652(12) 0.060(3) Uani 1 1 d . . . . .
H13A H 0.9165 0.5795 -0.1324 0.072 Uiso 1 1 calc R U . . .
C14A C 0.6392(19) 0.6032(4) 0.0215(12) 0.074(3) Uani 1 1 d . . . . .
H14A H 0.6714 0.6401 0.0189 0.088 Uiso 1 1 calc R U . . .
C15A C 0.4478(17) 0.5821(3) 0.1088(11) 0.055(2) Uani 1 1 d . . . . .
C16A C 0.3942(16) 0.5282(3) 0.1235(8) 0.0388(19) Uani 1 1 d . . . . .
H16A H 0.2584 0.5163 0.1872 0.047 Uiso 1 1 calc R U . . .
C21A C 0.6490(13) 0.3371(3) 0.0188(10) 0.051(3) Uani 1 1 d . . . . .
C22A C 0.467(2) 0.3111(3) 0.1019(14) 0.056(3) Uani 1 1 d . . . . .
H22A H 0.3484 0.3304 0.1626 0.068 Uiso 1 1 calc R U . . .
C23A C 0.456(2) 0.2537(3) 0.0973(15) 0.065(3) Uani 1 1 d . . . . .
H23A H 0.3383 0.2345 0.1593 0.078 Uiso 1 1 calc R U . . .
C24A C 0.629(2) 0.2274(4) -0.0042(11) 0.070(3) Uani 1 1 d . . . . .
H24A H 0.6171 0.1902 -0.0176 0.084 Uiso 1 1 calc R U . . .
C25A C 0.8138(19) 0.2550(4) -0.0833(14) 0.064(3) Uani 1 1 d . . . . .
H25A H 0.9320 0.2369 -0.1476 0.076 Uiso 1 1 calc R U . . .
C26A C 0.825(2) 0.3089(4) -0.0679(13) 0.060(3) Uani 1 1 d . . . . .
H26A H 0.9574 0.3276 -0.1184 0.072 Uiso 1 1 calc R U . . .
F12B F -0.142(2) -0.0230(4) -0.1482(13) 0.088(3) Uani 0.6 1 d . . P A -1
F15B F 0.474(2) 0.1151(4) 0.1824(14) 0.099(4) Uani 0.6 1 d . . P A -1
O1B O 0.503(2) -0.0816(5) 0.0877(17) 0.080(3) Uani 0.6 1 d . U P A -1
N1B N 0.095(3) -0.1070(7) 0.0189(19) 0.047(4) Uani 0.6 1 d . U P A -1
H1B H -0.0590 -0.0943 0.0096 0.056 Uiso 0.6 1 calc R U P A -1
C1B C 0.287(4) -0.0705(6) 0.0452(19) 0.060(4) Uani 0.6 1 d . U P A -1
C11B C 0.211(2) -0.0103(3) 0.0300(14) 0.054(3) Uani 0.6 1 d G U P A -1
C12B C 0.011(2) 0.0083(4) -0.0666(15) 0.060(4) Uani 0.6 1 d G U P A -1
C13B C -0.039(2) 0.0634(5) -0.0771(17) 0.060(4) Uani 0.6 1 d G U P A -1
H13B H -0.1729 0.0759 -0.1418 0.072 Uiso 0.6 1 calc R U P A -1
C14B C 0.112(3) 0.0998(3) 0.0091(19) 0.059(4) Uani 0.6 1 d G U P A -1
H14B H 0.0787 0.1366 0.0021 0.071 Uiso 0.6 1 calc R U P A -1
C15B C 0.312(2) 0.0811(4) 0.1058(17) 0.055(4) Uani 0.6 1 d G U P A -1
C16B C 0.3619(19) 0.0261(4) 0.1162(14) 0.054(3) Uani 0.6 1 d G U P A -1
H16B H 0.4960 0.0136 0.1809 0.065 Uiso 0.6 1 calc R U P A -1
F12D F 0.389(4) -0.0217(6) 0.168(2) 0.129(6) Uani 0.4 1 d . . P A -2
F15D F -0.235(5) 0.1149(6) -0.173(3) 0.173(8) Uani 0.4 1 d . . P A -2
O1D O -0.256(4) -0.0762(7) -0.078(3) 0.111(6) Uani 0.4 1 d . U P A -2
N1D N 0.162(6) -0.1059(14) -0.014(4) 0.086(8) Uani 0.4 1 d . U P A -2
H1D H 0.3193 -0.0947 -0.0113 0.103 Uiso 0.4 1 calc R U P A -2
C1D C -0.019(5) -0.0694(11) -0.037(4) 0.091(6) Uani 0.4 1 d . U P A -2
C11D C 0.061(5) -0.0101(6) -0.011(3) 0.081(5) Uani 0.4 1 d G U P A -2
C12D C 0.265(4) 0.0103(9) 0.080(3) 0.080(5) Uani 0.4 1 d G U P A -2
C13D C 0.309(4) 0.0657(9) 0.084(3) 0.081(6) Uani 0.4 1 d G U P A -2
H13D H 0.4460 0.0794 0.1445 0.098 Uiso 0.4 1 calc R U P A -2
C14D C 0.149(5) 0.1006(6) -0.001(4) 0.084(7) Uani 0.4 1 d G U P A -2
H14D H 0.1791 0.1376 0.0022 0.100 Uiso 0.4 1 calc R U P A -2
C15D C -0.055(5) 0.0801(8) -0.091(3) 0.079(6) Uani 0.4 1 d G U P A -2
C16D C -0.099(4) 0.0248(9) -0.096(2) 0.081(6) Uani 0.4 1 d G U P A -2
H16D H -0.2357 0.0111 -0.1561 0.098 Uiso 0.4 1 calc R U P A -2
C21B C 0.121(2) -0.1600(4) 0.0062(10) 0.072(3) Uani 1 1 d . . . . .
C22B C -0.065(2) -0.1883(4) -0.0915(14) 0.067(3) Uani 1 1 d . . . . .
H22B H -0.1839 -0.1697 -0.1544 0.080 Uiso 1 1 calc R U . . .
C23B C -0.060(3) -0.2452(5) -0.0886(16) 0.083(4) Uani 1 1 d . . . . .
H23B H -0.1874 -0.2640 -0.1437 0.100 Uiso 1 1 calc R U . . .
C24B C 0.1273(19) -0.2739(4) -0.0072(14) 0.080(4) Uani 1 1 d . . . . .
H24B H 0.1292 -0.3114 -0.0100 0.096 Uiso 1 1 calc R U . . .
C25B C 0.309(2) -0.2460(4) 0.0772(17) 0.084(4) Uani 1 1 d . . . . .
H25B H 0.4361 -0.2655 0.1314 0.101 Uiso 1 1 calc R U . . .
C26B C 0.315(2) -0.1905(4) 0.0866(15) 0.077(3) Uani 1 1 d . . . . .
H26B H 0.4443 -0.1732 0.1447 0.092 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
F12A C12A 1.363(9) . ?
F15A C15A 1.334(9) . ?
O1A C1A 1.211(9) . ?
N1A C1A 1.333(10) . ?
N1A C21A 1.489(10) . ?
N1A H1A 0.8600 . ?
C1A C11A 1.504(11) . ?
C11A C12A 1.370(9) . ?
C11A C16A 1.467(9) . ?
C12A C13A 1.366(9) . ?
C13A C14A 1.393(12) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.337(12) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.369(9) . ?
C16A H16A 0.9300 . ?
C21A C22A 1.337(12) . ?
C21A C26A 1.356(12) . ?
C22A C23A 1.422(11) . ?
C22A H22A 0.9300 . ?
C23A C24A 1.396(15) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.349(13) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.343(12) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
F12B C12B 1.298(11) . ?
F15B C15B 1.347(12) . ?
O1B C1B 1.202(18) . ?
N1B C21B 1.323(19) . ?
N1B C1B 1.37(2) . ?
N1B H1B 0.8600 . ?
C1B C11B 1.546(16) . ?
C11B C12B 1.3900 . ?
C11B C16B 1.3900 . ?
C12B C13B 1.3900 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9300 . ?
C14B C15B 1.3900 . ?
C14B H14B 0.9300 . ?
C15B C16B 1.3900 . ?
C16B H16B 0.9300 . ?
F12D C12D 1.26(2) . ?
F15D C15D 1.44(2) . ?
O1D C1D 1.28(3) . ?
N1D C1D 1.32(4) . ?
N1D C21B 1.37(3) . ?
N1D H1D 0.8600 . ?
C1D C11D 1.54(3) . ?
C11D C12D 1.3900 . ?
C11D C16D 1.3900 . ?
C12D C13D 1.3900 . ?
C13D C14D 1.3900 . ?
C13D H13D 0.9300 . ?
C14D C15D 1.3900 . ?
C14D H14D 0.9300 . ?
C15D C16D 1.3900 . ?
C16D H16D 0.9300 . ?
C21B C26B 1.424(13) . ?
C21B C22B 1.439(13) . ?
C22B C23B 1.408(13) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.378(14) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.362(14) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.377(13) . ?
C25B H25B 0.9300 . ?
C26B H26B 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
C1A N1A C21A 126.0(6) . . ?
C1A N1A H1A 117.0 . . ?
C21A N1A H1A 117.0 . . ?
O1A C1A N1A 124.3(7) . . ?
O1A C1A C11A 122.0(7) . . ?
N1A C1A C11A 113.7(7) . . ?
C12A C11A C16A 115.6(6) . . ?
C12A C11A C1A 130.1(7) . . ?
C16A C11A C1A 114.4(6) . . ?
F12A C12A C13A 119.3(7) . . ?
F12A C12A C11A 118.0(6) . . ?
C13A C12A C11A 122.7(7) . . ?
C12A C13A C14A 122.0(8) . . ?
C12A C13A H13A 119.0 . . ?
C14A C13A H13A 119.0 . . ?
C15A C14A C13A 116.0(7) . . ?
C15A C14A H14A 122.0 . . ?
C13A C14A H14A 122.0 . . ?
F15A C15A C14A 117.4(8) . . ?
F15A C15A C16A 117.1(7) . . ?
C14A C15A C16A 125.4(7) . . ?
C15A C16A C11A 118.2(6) . . ?
C15A C16A H16A 120.9 . . ?
C11A C16A H16A 120.9 . . ?
C22A C21A C26A 120.2(8) . . ?
C22A C21A N1A 120.7(8) . . ?
C26A C21A N1A 118.9(7) . . ?
C21A C22A C23A 119.7(10) . . ?
C21A C22A H22A 120.1 . . ?
C23A C22A H22A 120.1 . . ?
C24A C23A C22A 117.2(11) . . ?
C24A C23A H23A 121.4 . . ?
C22A C23A H23A 121.4 . . ?
C25A C24A C23A 121.1(9) . . ?
C25A C24A H24A 119.5 . . ?
C23A C24A H24A 119.5 . . ?
C26A C25A C24A 119.2(10) . . ?
C26A C25A H25A 120.4 . . ?
C24A C25A H25A 120.4 . . ?
C25A C26A C21A 122.2(9) . . ?
C25A C26A H26A 118.9 . . ?
C21A C26A H26A 118.9 . . ?
C21B N1B C1B 126.5(16) . . ?
C21B N1B H1B 116.7 . . ?
C1B N1B H1B 116.7 . . ?
O1B C1B N1B 125.0(16) . . ?
O1B C1B C11B 118.8(15) . . ?
N1B C1B C11B 116.0(15) . . ?
C12B C11B C16B 120.0 . . ?
C12B C11B C1B 123.9(9) . . ?
C16B C11B C1B 116.1(9) . . ?
F12B C12B C11B 123.8(10) . . ?
F12B C12B C13B 116.2(10) . . ?
C11B C12B C13B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C15B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
F15B C15B C14B 121.8(9) . . ?
F15B C15B C16B 118.0(9) . . ?
C14B C15B C16B 120.0 . . ?
C15B C16B C11B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C11B C16B H16B 120.0 . . ?
C1D N1D C21B 125(3) . . ?
C1D N1D H1D 117.4 . . ?
C21B N1D H1D 117.4 . . ?
O1D C1D N1D 129(3) . . ?
O1D C1D C11D 115(2) . . ?
N1D C1D C11D 116(2) . . ?
C12D C11D C16D 120.0 . . ?
C12D C11D C1D 128.9(18) . . ?
C16D C11D C1D 111.1(18) . . ?
F12D C12D C11D 118.1(19) . . ?
F12D C12D C13D 121.5(19) . . ?
C11D C12D C13D 120.0 . . ?
C14D C13D C12D 120.0 . . ?
C14D C13D H13D 120.0 . . ?
C12D C13D H13D 120.0 . . ?
C15D C14D C13D 120.0 . . ?
C15D C14D H14D 120.0 . . ?
C13D C14D H14D 120.0 . . ?
C14D C15D C16D 120.0 . . ?
C14D C15D F15D 121.9(16) . . ?
C16D C15D F15D 118.0(16) . . ?
C15D C16D C11D 120.0 . . ?
C15D C16D H16D 120.0 . . ?
C11D C16D H16D 120.0 . . ?
N1B C21B C26B 124.2(12) . . ?
N1D C21B C26B 117.8(16) . . ?
N1B C21B C22B 117.4(11) . . ?
N1D C21B C22B 120.9(17) . . ?
C26B C21B C22B 118.4(9) . . ?
C23B C22B C21B 117.7(10) . . ?
C23B C22B H22B 121.1 . . ?
C21B C22B H22B 121.1 . . ?
C24B C23B C22B 122.5(10) . . ?
C24B C23B H23B 118.7 . . ?
C22B C23B H23B 118.7 . . ?
C25B C24B C23B 118.4(9) . . ?
C25B C24B H24B 120.8 . . ?
C23B C24B H24B 120.8 . . ?
C24B C25B C26B 123.3(9) . . ?
C24B C25B H25B 118.3 . . ?
C26B C25B H25B 118.3 . . ?
C25B C26B C21B 119.2(10) . . ?
C25B C26B H26B 120.4 . . ?
C21B C26B H26B 120.4 . . ?

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
C21A N1A C1A O1A 6.4(14) . . . . ?
C21A N1A C1A C11A -171.3(7) . . . . ?
O1A C1A C11A C12A -155.1(8) . . . . ?
N1A C1A C11A C12A 22.7(12) . . . . ?
O1A C1A C11A C16A 24.1(11) . . . . ?
N1A C1A C11A C16A -158.1(7) . . . . ?
C16A C11A C12A F12A -179.4(7) . . . . ?
C1A C11A C12A F12A -0.2(12) . . . . ?
C16A C11A C12A C13A -0.8(9) . . . . ?
C1A C11A C12A C13A 178.4(8) . . . . ?
F12A C12A C13A C14A -178.5(9) . . . . ?
C11A C12A C13A C14A 2.9(12) . . . . ?
C12A C13A C14A C15A -3.6(13) . . . . ?
C13A C14A C15A F15A 179.4(9) . . . . ?
C13A C14A C15A C16A 2.5(13) . . . . ?
F15A C15A C16A C11A -177.5(8) . . . . ?
C14A C15A C16A C11A -0.6(11) . . . . ?
C12A C11A C16A C15A -0.4(8) . . . . ?
C1A C11A C16A C15A -179.7(7) . . . . ?
C1A N1A C21A C22A -27.9(13) . . . . ?
C1A N1A C21A C26A 156.1(9) . . . . ?
C26A C21A C22A C23A -1.0(13) . . . . ?
N1A C21A C22A C23A -177.0(9) . . . . ?
C21A C22A C23A C24A -4.0(16) . . . . ?
C22A C23A C24A C25A 5.7(14) . . . . ?
C23A C24A C25A C26A -2.3(14) . . . . ?
C24A C25A C26A C21A -3.1(16) . . . . ?
C22A C21A C26A C25A 4.7(14) . . . . ?
N1A C21A C26A C25A -179.2(10) . . . . ?
C21B N1B C1B O1B -13(3) . . . . ?
C21B N1B C1B C11B 171.3(13) . . . . ?
O1B C1B C11B C12B 156.9(13) . . . . ?
N1B C1B C11B C12B -27.4(18) . . . . ?
O1B C1B C11B C16B -21.0(18) . . . . ?
N1B C1B C11B C16B 154.6(12) . . . . ?
C16B C11B C12B F12B -178.5(14) . . . . ?
C1B C11B C12B F12B 3.6(16) . . . . ?
C16B C11B C12B C13B 0.0 . . . . ?
C1B C11B C12B C13B -177.9(13) . . . . ?
F12B C12B C13B C14B 178.6(13) . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C13B C14B C15B F15B 175.4(14) . . . . ?
C13B C14B C15B C16B 0.0 . . . . ?
F15B C15B C16B C11B -175.5(14) . . . . ?
C14B C15B C16B C11B 0.0 . . . . ?
C12B C11B C16B C15B 0.0 . . . . ?
C1B C11B C16B C15B 178.0(12) . . . . ?
C21B N1D C1D O1D -16(6) . . . . ?
C21B N1D C1D C11D 164(2) . . . . ?
O1D C1D C11D C12D 158(2) . . . . ?
N1D C1D C11D C12D -22(4) . . . . ?
O1D C1D C11D C16D -24(3) . . . . ?
N1D C1D C11D C16D 156(2) . . . . ?
C16D C11D C12D F12D 173(2) . . . . ?
C1D C11D C12D F12D -9(3) . . . . ?
C16D C11D C12D C13D 0.0 . . . . ?
C1D C11D C12D C13D 178(3) . . . . ?
F12D C12D C13D C14D -172(2) . . . . ?
C11D C12D C13D C14D 0.0 . . . . ?
C12D C13D C14D C15D 0.0 . . . . ?
C13D C14D C15D C16D 0.0 . . . . ?
C13D C14D C15D F15D 176(2) . . . . ?
C14D C15D C16D C11D 0.0 . . . . ?
F15D C15D C16D C11D -176(2) . . . . ?
C12D C11D C16D C15D 0.0 . . . . ?
C1D C11D C16D C15D -179(2) . . . . ?
C1B N1B C21B C26B 30(2) . . . . ?
C1B N1B C21B C22B -151.5(15) . . . . ?
C1D N1D C21B C26B -157(3) . . . . ?
C1D N1D C21B C22B 42(4) . . . . ?
N1B C21B C22B C23B -171.7(13) . . . . ?
N1D C21B C22B C23B 166.9(17) . . . . ?
C26B C21B C22B C23B 6.5(13) . . . . ?
C21B C22B C23B C24B -5.4(18) . . . . ?
C22B C23B C24B C25B 2.0(17) . . . . ?
C23B C24B C25B C26B 0.5(19) . . . . ?
C24B C25B C26B C21B 1(2) . . . . ?
N1B C21B C26B C25B 173.7(13) . . . . ?
N1D C21B C26B C25B -165.4(18) . . . . ?
C22B C21B C26B C25B -4.3(14) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A O1A 0.86 2.40 3.170(9) 149 1_655 yes
N1A H1A F12A 0.86 2.14 2.729(8) 125 . yes
N1B H1B F12B 0.86 2.24 2.785(19) 121 . yes
N1D H1D F12D 0.86 2.37 2.83(4) 114 . yes

#   Intermolecular N-H...O=C interaction and Intramolecular N-H...F
#
#    Crystals grown from n-hexane

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_F2_26_294K
_database_code_depnum_ccdc_archive 'CCDC 1453276'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(F2_26 or 11-045)'
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.0951(3)
_cell_length_b                   12.1037(3)
_cell_length_c                   16.9753(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.195(2)
_cell_angle_gamma                90
_cell_volume                     2273.54(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4753
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            21895
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6011
_reflns_number_gt                3551
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0629P)²+0.578P] 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         6011
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.030

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
F22A F 0.34889(19) 0.20858(15) 0.35217(10) 0.1276(7) Uani 1 1 d . . . . .
F26A F 0.50814(16) 0.11405(12) 0.11627(9) 0.1084(5) Uani 1 1 d . . . . .
O1A O 0.60041(15) 0.28557(12) 0.31974(9) 0.0824(5) Uani 1 1 d . . . . .
C1A C 0.54290(17) 0.33145(15) 0.26517(10) 0.0568(4) Uani 1 1 d . . . . .
N1A N 0.45714(15) 0.27678(13) 0.21972(9) 0.0615(4) Uani 1 1 d . . . . .
H1A H 0.4231(19) 0.3058(17) 0.1756(13) 0.070(6) Uiso 1 1 d . . . . .
C11A C 0.56400(17) 0.44897(15) 0.24550(10) 0.0575(4) Uani 1 1 d . . . . .
C12A C 0.6745(2) 0.4955(2) 0.26698(15) 0.0863(7) Uani 1 1 d . . . . .
H12A H 0.7345 0.4527 0.2931 0.104 Uiso 1 1 calc R U . . .
C13A C 0.6980(3) 0.6041(2) 0.25055(19) 0.1051(9) Uani 1 1 d . . . . .
H13A H 0.7738 0.6336 0.2650 0.126 Uiso 1 1 calc R U . . .
C14A C 0.6125(3) 0.6682(2) 0.21371(16) 0.0964(8) Uani 1 1 d . . . . .
H14A H 0.6289 0.7417 0.2024 0.116 Uiso 1 1 calc R U . . .
C15A C 0.5024(3) 0.6248(2) 0.19331(18) 0.1071(10) Uani 1 1 d . . . . .
H15A H 0.4425 0.6692 0.1687 0.128 Uiso 1 1 calc R U . . .
C16A C 0.4774(2) 0.51504(19) 0.20857(15) 0.0862(7) Uani 1 1 d . . . . .
H16A H 0.4015 0.4862 0.1936 0.103 Uiso 1 1 calc R U . . .
C21A C 0.43008(17) 0.16555(15) 0.23383(11) 0.0581(4) Uani 1 1 d . . . . .
C22A C 0.3775(2) 0.1312(2) 0.30034(13) 0.0772(6) Uani 1 1 d . . . . .
C23A C 0.3537(2) 0.0226(2) 0.31544(17) 0.0923(8) Uani 1 1 d . . . . .
H23A H 0.3189 0.0025 0.3615 0.111 Uiso 1 1 calc R U . . .
C24A C 0.3816(2) -0.0552(2) 0.26230(18) 0.0927(8) Uani 1 1 d . . . . .
H24A H 0.3653 -0.1292 0.2719 0.111 Uiso 1 1 calc R U . . .
C25A C 0.4331(2) -0.0261(2) 0.19495(17) 0.0898(7) Uani 1 1 d . . . . .
H25A H 0.4521 -0.0793 0.1583 0.108 Uiso 1 1 calc R U . . .
C26A C 0.4563(2) 0.08306(18) 0.18249(13) 0.0711(5) Uani 1 1 d . . . . .
F22B F 0.0471(2) 0.2022(2) 0.07884(16) 0.1866(11) Uani 1 1 d . . . . .
F26B F 0.36288(19) 0.11386(14) -0.07072(12) 0.1324(7) Uani 1 1 d . . . . .
O1B O 0.31390(16) 0.33760(13) 0.07921(8) 0.0875(5) Uani 1 1 d . . . . .
C1B C 0.26188(17) 0.35320(16) 0.01463(10) 0.0595(5) Uani 1 1 d . . . . .
N1B N 0.20710(18) 0.27085(14) -0.02642(10) 0.0686(5) Uani 1 1 d . . . . .
H1B H 0.179(2) 0.2820(18) -0.0733(14) 0.072(6) Uiso 1 1 d . . . . .
C11B C 0.25452(18) 0.46513(16) -0.02159(10) 0.0606(5) Uani 1 1 d . . . . .
C12B C 0.3431(2) 0.5405(2) -0.00073(14) 0.0809(6) Uani 1 1 d . . . . .
H12B H 0.4072 0.5205 0.0348 0.097 Uiso 1 1 calc R U . . .
C13B C 0.3384(3) 0.6464(2) -0.03193(18) 0.1003(8) Uani 1 1 d . . . . .
H13B H 0.4001 0.6963 -0.0181 0.120 Uiso 1 1 calc R U . . .
C14B C 0.2456(4) 0.6770(2) -0.08175(17) 0.1133(11) Uani 1 1 d . . . . .
H14B H 0.2423 0.7483 -0.1022 0.136 Uiso 1 1 calc R U . . .
C15B C 0.1570(4) 0.6042(2) -0.1023(2) 0.1367(15) Uani 1 1 d . . . . .
H15B H 0.0925 0.6259 -0.1369 0.164 Uiso 1 1 calc R U . . .
C16B C 0.1603(3) 0.4982(2) -0.07282(16) 0.1050(10) Uani 1 1 d . . . . .
H16B H 0.0984 0.4490 -0.0877 0.126 Uiso 1 1 calc R U . . .
C21B C 0.2037(2) 0.16147(17) 0.00234(11) 0.0647(5) Uani 1 1 d . . . . .
C22B C 0.1228(3) 0.1259(3) 0.05306(17) 0.1044(9) Uani 1 1 d . . . . .
C23B C 0.1169(4) 0.0145(4) 0.0769(2) 0.1293(12) Uani 1 1 d . . . . .
H23B H 0.0606 -0.0088 0.1113 0.155 Uiso 1 1 calc R U . . .
C24B C 0.1956(4) -0.0568(3) 0.0482(2) 0.1237(12) Uani 1 1 d . . . . .
H24B H 0.1924 -0.1308 0.0625 0.148 Uiso 1 1 calc R U . . .
C25B C 0.2773(4) -0.0250(2) 0.00030(18) 0.1164(11) Uani 1 1 d . . . . .
H25B H 0.3319 -0.0755 -0.0180 0.140 Uiso 1 1 calc R U . . .
C26B C 0.2801(3) 0.08221(18) -0.02171(14) 0.0832(7) 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
F22A C22A 1.339(3) . ?
F26A C26A 1.353(2) . ?
O1A C1A 1.220(2) . ?
C1A N1A 1.353(2) . ?
C1A C11A 1.484(3) . ?
N1A C21A 1.404(2) . ?
N1A H1A 0.89(2) . ?
C11A C16A 1.366(3) . ?
C11A C12A 1.374(3) . ?
C12A C13A 1.373(4) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.344(4) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.352(4) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.385(3) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21A C26A 1.370(3) . ?
C21A C22A 1.373(3) . ?
C22A C23A 1.368(3) . ?
C23A C24A 1.356(4) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.362(4) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.365(3) . ?
C25A H25A 0.9300 . ?
F22B C22B 1.343(4) . ?
F26B C26B 1.339(3) . ?
O1B C1B 1.216(2) . ?
C1B N1B 1.337(2) . ?
C1B C11B 1.488(3) . ?
N1B C21B 1.413(3) . ?
N1B H1B 0.84(2) . ?
C11B C12B 1.369(3) . ?
C11B C16B 1.370(3) . ?
C12B C13B 1.386(3) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.336(4) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.347(5) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.376(4) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21B C22B 1.358(3) . ?
C21B C26B 1.363(3) . ?
C22B C23B 1.410(5) . ?
C23B C24B 1.344(5) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.318(4) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.351(3) . ?
C25B H25B 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
O1A C1A N1A 121.17(18) . . ?
O1A C1A C11A 121.67(17) . . ?
N1A C1A C11A 117.16(15) . . ?
C1A N1A C21A 121.46(15) . . ?
C1A N1A H1A 121.8(13) . . ?
C21A N1A H1A 116.2(13) . . ?
C16A C11A C12A 117.7(2) . . ?
C16A C11A C1A 123.17(18) . . ?
C12A C11A C1A 119.06(18) . . ?
C13A C12A C11A 121.2(2) . . ?
C13A C12A H12A 119.4 . . ?
C11A C12A H12A 119.4 . . ?
C14A C13A C12A 120.6(3) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C13A C14A C15A 119.2(2) . . ?
C13A C14A H14A 120.4 . . ?
C15A C14A H14A 120.4 . . ?
C14A C15A C16A 121.0(2) . . ?
C14A C15A H15A 119.5 . . ?
C16A C15A H15A 119.5 . . ?
C11A C16A C15A 120.2(2) . . ?
C11A C16A H16A 119.9 . . ?
C15A C16A H16A 119.9 . . ?
C26A C21A C22A 115.16(19) . . ?
C26A C21A N1A 122.16(18) . . ?
C22A C21A N1A 122.68(18) . . ?
F22A C22A C23A 119.4(2) . . ?
F22A C22A C21A 117.6(2) . . ?
C23A C22A C21A 123.0(2) . . ?
C24A C23A C22A 119.1(2) . . ?
C24A C23A H23A 120.5 . . ?
C22A C23A H23A 120.5 . . ?
C23A C24A C25A 120.6(2) . . ?
C23A C24A H24A 119.7 . . ?
C25A C24A H24A 119.7 . . ?
C24A C25A C26A 118.4(2) . . ?
C24A C25A H25A 120.8 . . ?
C26A C25A H25A 120.8 . . ?
F26A C26A C25A 119.6(2) . . ?
F26A C26A C21A 116.70(18) . . ?
C25A C26A C21A 123.7(2) . . ?
O1B C1B N1B 121.48(19) . . ?
O1B C1B C11B 121.48(18) . . ?
N1B C1B C11B 117.03(16) . . ?
C1B N1B C21B 122.78(17) . . ?
C1B N1B H1B 119.6(15) . . ?
C21B N1B H1B 117.3(15) . . ?
C12B C11B C16B 118.0(2) . . ?
C12B C11B C1B 118.92(18) . . ?
C16B C11B C1B 123.0(2) . . ?
C11B C12B C13B 120.7(2) . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B H12B 119.6 . . ?
C14B C13B C12B 120.3(3) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 119.8(3) . . ?
C13B C14B H14B 120.1 . . ?
C15B C14B H14B 120.1 . . ?
C14B C15B C16B 121.0(3) . . ?
C14B C15B H15B 119.5 . . ?
C16B C15B H15B 119.5 . . ?
C11B C16B C15B 120.1(3) . . ?
C11B C16B H16B 119.9 . . ?
C15B C16B H16B 119.9 . . ?
C22B C21B C26B 114.9(2) . . ?
C22B C21B N1B 123.5(2) . . ?
C26B C21B N1B 121.5(2) . . ?
F22B C22B C21B 116.5(3) . . ?
F22B C22B C23B 121.4(3) . . ?
C21B C22B C23B 122.1(3) . . ?
C24B C23B C22B 117.7(3) . . ?
C24B C23B H23B 121.2 . . ?
C22B C23B H23B 121.2 . . ?
C25B C24B C23B 122.0(3) . . ?
C25B C24B H24B 119.0 . . ?
C23B C24B H24B 119.0 . . ?
C24B C25B C26B 118.8(3) . . ?
C24B C25B H25B 120.6 . . ?
C26B C25B H25B 120.6 . . ?
F26B C26B C25B 118.5(3) . . ?
F26B C26B C21B 117.05(19) . . ?
C25B C26B C21B 124.4(3) . . ?

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
O1A C1A N1A C21A 0.6(3) . . . . ?
C11A C1A N1A C21A -179.68(16) . . . . ?
O1A C1A C11A C16A -153.8(2) . . . . ?
N1A C1A C11A C16A 26.5(3) . . . . ?
O1A C1A C11A C12A 24.5(3) . . . . ?
N1A C1A C11A C12A -155.3(2) . . . . ?
C16A C11A C12A C13A -1.2(4) . . . . ?
C1A C11A C12A C13A -179.6(2) . . . . ?
C11A C12A C13A C14A 0.8(5) . . . . ?
C12A C13A C14A C15A 0.4(5) . . . . ?
C13A C14A C15A C16A -1.1(5) . . . . ?
C12A C11A C16A C15A 0.5(4) . . . . ?
C1A C11A C16A C15A 178.7(2) . . . . ?
C14A C15A C16A C11A 0.7(5) . . . . ?
C1A N1A C21A C26A -111.8(2) . . . . ?
C1A N1A C21A C22A 67.1(3) . . . . ?
C26A C21A C22A F22A -179.4(2) . . . . ?
N1A C21A C22A F22A 1.7(3) . . . . ?
C26A C21A C22A C23A 0.7(3) . . . . ?
N1A C21A C22A C23A -178.3(2) . . . . ?
F22A C22A C23A C24A 179.2(2) . . . . ?
C21A C22A C23A C24A -0.8(4) . . . . ?
C22A C23A C24A C25A 0.3(4) . . . . ?
C23A C24A C25A C26A 0.2(4) . . . . ?
C24A C25A C26A F26A 179.6(2) . . . . ?
C24A C25A C26A C21A -0.3(4) . . . . ?
C22A C21A C26A F26A 179.96(19) . . . . ?
N1A C21A C26A F26A -1.0(3) . . . . ?
C22A C21A C26A C25A -0.1(3) . . . . ?
N1A C21A C26A C25A 178.9(2) . . . . ?
O1B C1B N1B C21B 1.2(3) . . . . ?
C11B C1B N1B C21B -177.77(18) . . . . ?
O1B C1B C11B C12B 26.7(3) . . . . ?
N1B C1B C11B C12B -154.4(2) . . . . ?
O1B C1B C11B C16B -150.6(2) . . . . ?
N1B C1B C11B C16B 28.3(3) . . . . ?
C16B C11B C12B C13B -1.3(4) . . . . ?
C1B C11B C12B C13B -178.7(2) . . . . ?
C11B C12B C13B C14B 1.4(4) . . . . ?
C12B C13B C14B C15B -0.6(5) . . . . ?
C13B C14B C15B C16B -0.1(6) . . . . ?
C12B C11B C16B C15B 0.5(4) . . . . ?
C1B C11B C16B C15B 177.9(3) . . . . ?
C14B C15B C16B C11B 0.2(6) . . . . ?
C1B N1B C21B C22B 82.1(3) . . . . ?
C1B N1B C21B C26B -100.3(3) . . . . ?
C26B C21B C22B F22B 179.1(3) . . . . ?
N1B C21B C22B F22B -3.2(4) . . . . ?
C26B C21B C22B C23B -1.7(4) . . . . ?
N1B C21B C22B C23B 176.0(3) . . . . ?
F22B C22B C23B C24B 179.7(3) . . . . ?
C21B C22B C23B C24B 0.6(5) . . . . ?
C22B C23B C24B C25B 1.0(6) . . . . ?
C23B C24B C25B C26B -1.3(6) . . . . ?
C24B C25B C26B F26B -179.6(3) . . . . ?
C24B C25B C26B C21B 0.0(5) . . . . ?
C22B C21B C26B F26B -178.9(2) . . . . ?
N1B C21B C26B F26B 3.3(3) . . . . ?
C22B C21B C26B C25B 1.4(4) . . . . ?
N1B C21B C26B C25B -176.4(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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A O1B 0.89(2) 2.00(2) 2.864(2) 164.2(19) . yes
N1B H1B O1A 0.84(2) 2.12(2) 2.870(2) 148(2) 4_565 yes
C24B H24B F22A 0.93 2.49 3.361(4) 157 2_545 yes
C25B H25B F26A 0.93 2.57 3.382(4) 147 3_655 yes

#
#    Crystals grown from CHCl3

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_26_F2_294K
_database_code_depnum_ccdc_archive 'CCDC 1453277'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(26_F2 or 11-018)'
_chemical_name_common            ?
_chemical_melting_point          402
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.1031(18)
_cell_length_b                   21.838(3)
_cell_length_c                   4.8875(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1078.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2293
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      27.38

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Empirical - ABSPACK'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            7275
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.450
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_point_group_measured_fraction_full 0.838
_reflns_number_total             1980
_reflns_number_gt                1187
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.480
_reflns_Friedel_fraction_max     0.588
_reflns_Friedel_fraction_full    0.634

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0311P)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_abs_structure_details 
;
Flack x from 298 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.8(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1980
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_restrained_S_all      0.848
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.025

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
F12 F 0.70504(17) 0.21904(6) -0.2881(4) 0.0731(5) Uani 1 1 d . . . . .
F16 F 0.38804(15) 0.32590(7) 0.2188(4) 0.0727(5) Uani 1 1 d . . . . .
O1 O 0.6306(2) 0.34167(9) -0.3877(3) 0.0659(6) Uani 1 1 d . . . . .
N1 N 0.6297(2) 0.37738(10) 0.0454(4) 0.0464(5) Uani 1 1 d . . . . .
H1 H 0.610(2) 0.3696(11) 0.228(6) 0.063(7) Uiso 1 1 d . . . . .
C1 C 0.6070(3) 0.33481(12) -0.1458(5) 0.0436(7) Uani 1 1 d . . . . .
C11 C 0.5514(3) 0.27622(12) -0.0387(5) 0.0394(6) Uani 1 1 d . . . . .
C12 C 0.6018(3) 0.22027(13) -0.1158(5) 0.0472(7) Uani 1 1 d . . . . .
C13 C 0.5559(3) 0.16592(12) -0.0204(6) 0.0550(7) Uani 1 1 d . . . . .
H13 H 0.5936 0.1293 -0.0782 0.066 Uiso 1 1 calc R U . . .
C14 C 0.4527(3) 0.16584(13) 0.1633(5) 0.0598(8) Uani 1 1 d . . . . .
H14 H 0.4212 0.1290 0.2329 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3963(3) 0.21984(13) 0.2437(6) 0.0573(8) Uani 1 1 d . . . . .
H15 H 0.3253 0.2202 0.3649 0.069 Uiso 1 1 calc R U . . .
C16 C 0.4464(3) 0.27288(12) 0.1423(5) 0.0489(7) Uani 1 1 d . . . . .
C21 C 0.6802(2) 0.43709(12) 0.0030(5) 0.0452(6) Uani 1 1 d . . . . .
C22 C 0.7768(3) 0.45020(15) -0.1869(5) 0.0637(8) Uani 1 1 d . . . . .
H22 H 0.8098 0.4193 -0.2985 0.076 Uiso 1 1 calc R U . . .
C23 C 0.8246(3) 0.50897(16) -0.2122(7) 0.0758(9) Uani 1 1 d . . . . .
H23 H 0.8899 0.5176 -0.3406 0.091 Uiso 1 1 calc R U . . .
C24 C 0.7766(4) 0.55449(14) -0.0503(8) 0.0738(10) Uani 1 1 d . . . . .
H24 H 0.8081 0.5943 -0.0697 0.089 Uiso 1 1 calc R U . . .
C25 C 0.6818(3) 0.54156(14) 0.1410(7) 0.0721(9) Uani 1 1 d . . . . .
H25 H 0.6502 0.5725 0.2543 0.087 Uiso 1 1 calc R U . . .
C26 C 0.6334(3) 0.48325(12) 0.1665(6) 0.0584(7) Uani 1 1 d . . . . .
H26 H 0.5683 0.4749 0.2957 0.070 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
F12 C12 1.341(3) . ?
F16 C16 1.352(3) . ?
O1 C1 1.216(3) . ?
N1 C1 1.338(3) . ?
N1 C21 1.416(3) . ?
N1 H1 0.93(3) . ?
C1 C11 1.492(3) . ?
C11 C12 1.376(3) . ?
C11 C16 1.384(3) . ?
C12 C13 1.357(3) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(3) . ?
C15 H15 0.9300 . ?
C21 C26 1.370(4) . ?
C21 C22 1.377(4) . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(4) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 N1 C21 126.9(2) . . ?
C1 N1 H1 120.4(15) . . ?
C21 N1 H1 112.7(15) . . ?
O1 C1 N1 124.1(3) . . ?
O1 C1 C11 121.4(2) . . ?
N1 C1 C11 114.6(2) . . ?
C12 C11 C16 114.3(2) . . ?
C12 C11 C1 121.8(2) . . ?
C16 C11 C1 123.9(2) . . ?
F12 C12 C13 117.7(2) . . ?
F12 C12 C11 118.5(2) . . ?
C13 C12 C11 123.8(2) . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F16 C16 C15 117.8(2) . . ?
F16 C16 C11 117.8(2) . . ?
C15 C16 C11 124.4(3) . . ?
C26 C21 C22 119.0(3) . . ?
C26 C21 N1 117.9(2) . . ?
C22 C21 N1 123.1(3) . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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
C21 N1 C1 O1 2.0(5) . . . . ?
C21 N1 C1 C11 -179.2(2) . . . . ?
O1 C1 C11 C12 46.1(4) . . . . ?
N1 C1 C11 C12 -132.8(3) . . . . ?
O1 C1 C11 C16 -133.6(3) . . . . ?
N1 C1 C11 C16 47.5(3) . . . . ?
C16 C11 C12 F12 -179.1(2) . . . . ?
C1 C11 C12 F12 1.1(3) . . . . ?
C16 C11 C12 C13 -1.4(3) . . . . ?
C1 C11 C12 C13 178.9(2) . . . . ?
F12 C12 C13 C14 178.0(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 -1.3(4) . . . . ?
C14 C15 C16 F16 178.6(2) . . . . ?
C14 C15 C16 C11 0.1(4) . . . . ?
C12 C11 C16 F16 -177.4(2) . . . . ?
C1 C11 C16 F16 2.4(3) . . . . ?
C12 C11 C16 C15 1.2(3) . . . . ?
C1 C11 C16 C15 -179.1(3) . . . . ?
C1 N1 C21 C26 144.9(3) . . . . ?
C1 N1 C21 C22 -37.5(4) . . . . ?
C26 C21 C22 C23 -0.4(4) . . . . ?
N1 C21 C22 C23 -178.0(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C23 C24 C25 C26 -1.2(5) . . . . ?
C24 C25 C26 C21 0.7(4) . . . . ?
C22 C21 C26 C25 0.1(4) . . . . ?
N1 C21 C26 C25 177.8(2) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 O1 0.93(3) 1.99(3) 2.878(2) 160(2) 1_556 yes
N1 H1 F16 0.93(3) 2.44(2) 2.818(3) 104.6(18) . yes
C15 H15 F12 0.93 2.47 3.279(3) 145 3_456 yes
C15 H15 O1 0.93 2.68 3.500(3) 148 3_456 yes
C22 H22 O1 0.93 2.52 2.960(4) 109 . yes

#
#    Crystals grown from n-hexane

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_F2_34_294K
_database_code_depnum_ccdc_archive 'CCDC 1453278'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(F2_34 or 11-036)'
_chemical_name_common            ?
_chemical_melting_point          434
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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                   5.4841(3)
_cell_length_b                   7.8068(6)
_cell_length_c                   12.6875(5)
_cell_angle_alpha                106.756(5)
_cell_angle_beta                 98.878(4)
_cell_angle_gamma                90.151(5)
_cell_volume                     513.26(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2383
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      29.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            4632
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         29.485
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2666
_reflns_number_gt                2320
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0578P)²+0.1272P] 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         2666
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039

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
F23 F 0.61300(16) 0.49395(13) 0.90599(6) 0.0536(3) Uani 1 1 d . . . . .
F24 F 1.01761(18) 0.71152(13) 0.96949(7) 0.0575(3) Uani 1 1 d . . . . .
O1 O 0.39066(17) 0.25162(16) 0.50617(8) 0.0502(3) Uani 1 1 d . . . . .
C1 C 0.5862(2) 0.21669(16) 0.47158(9) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.81061(19) 0.27465(14) 0.53531(8) 0.0336(2) Uani 1 1 d . . . . .
H1 H 0.937(3) 0.259(2) 0.5043(13) 0.041(4) Uiso 1 1 d . . . . .
C11 C 0.5928(2) 0.10817(15) 0.35372(9) 0.0295(2) Uani 1 1 d . . . . .
C12 C 0.3902(2) 0.11344(17) 0.27423(10) 0.0347(3) Uani 1 1 d . . . . .
H12 H 0.2587 0.1830 0.2954 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3831(2) 0.01554(18) 0.16356(10) 0.0395(3) Uani 1 1 d . . . . .
H13 H 0.2482 0.0208 0.1105 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5771(3) -0.09002(18) 0.13212(10) 0.0401(3) Uani 1 1 d . . . . .
H14 H 0.5719 -0.1564 0.0580 0.048 Uiso 1 1 calc R U . . .
C15 C 0.7784(2) -0.09677(17) 0.21088(11) 0.0392(3) Uani 1 1 d . . . . .
H15 H 0.9081 -0.1683 0.1896 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7881(2) 0.00251(16) 0.32145(10) 0.0341(3) Uani 1 1 d . . . . .
H16 H 0.9247 -0.0014 0.3740 0.041 Uiso 1 1 calc R U . . .
C21 C 0.8542(2) 0.38687(15) 0.64677(9) 0.0297(2) Uani 1 1 d . . . . .
C22 C 0.6979(2) 0.38238(17) 0.72273(9) 0.0335(3) Uani 1 1 d . . . . .
H22 H 0.5561 0.3070 0.7014 0.040 Uiso 1 1 calc R U . . .
C23 C 0.7594(2) 0.49306(18) 0.83062(9) 0.0356(3) Uani 1 1 d . . . . .
C24 C 0.9688(2) 0.60444(17) 0.86318(10) 0.0378(3) Uani 1 1 d . . . . .
C25 C 1.1234(2) 0.60930(18) 0.78898(11) 0.0396(3) Uani 1 1 d . . . . .
H25 H 1.2649 0.6850 0.8113 0.048 Uiso 1 1 calc R U . . .
C26 C 1.0660(2) 0.49972(17) 0.68005(10) 0.0349(3) Uani 1 1 d . . . . .
H26 H 1.1698 0.5018 0.6289 0.042 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
F23 C23 1.3389(14) . ?
F24 C24 1.3517(13) . ?
O1 C1 1.2225(14) . ?
C1 N1 1.3610(15) . ?
C1 C11 1.4972(15) . ?
N1 C21 1.4159(13) . ?
N1 H1 0.843(16) . ?
C11 C12 1.3897(16) . ?
C11 C16 1.3930(16) . ?
C12 C13 1.3861(16) . ?
C12 H12 0.9300 . ?
C13 C14 1.3842(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.3822(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.3862(16) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.3898(16) . ?
C21 C22 1.3928(16) . ?
C22 C23 1.3813(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.3735(19) . ?
C24 C25 1.3687(19) . ?
C25 C26 1.3870(17) . ?
C25 H25 0.9300 . ?
C26 H26 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
O1 C1 N1 123.22(10) . . ?
O1 C1 C11 121.40(10) . . ?
N1 C1 C11 115.38(10) . . ?
C1 N1 C21 126.42(10) . . ?
C1 N1 H1 118.7(11) . . ?
C21 N1 H1 114.0(11) . . ?
C12 C11 C16 119.45(10) . . ?
C12 C11 C1 117.21(10) . . ?
C16 C11 C1 123.33(10) . . ?
C13 C12 C11 120.35(11) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.93(11) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.02(11) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.34(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.90(11) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C26 C21 C22 120.25(10) . . ?
C26 C21 N1 117.50(10) . . ?
C22 C21 N1 122.22(10) . . ?
C23 C22 C21 118.09(11) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
F23 C23 C24 118.52(11) . . ?
F23 C23 C22 119.99(11) . . ?
C24 C23 C22 121.49(11) . . ?
F24 C24 C25 120.49(12) . . ?
F24 C24 C23 118.80(12) . . ?
C25 C24 C23 120.70(11) . . ?
C24 C25 C26 119.04(12) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 120.43(11) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?

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
O1 C1 N1 C21 -2.6(2) . . . . ?
C11 C1 N1 C21 176.33(11) . . . . ?
O1 C1 C11 C12 27.12(18) . . . . ?
N1 C1 C11 C12 -151.86(12) . . . . ?
O1 C1 C11 C16 -152.01(13) . . . . ?
N1 C1 C11 C16 29.01(17) . . . . ?
C16 C11 C12 C13 -0.49(19) . . . . ?
C1 C11 C12 C13 -179.66(11) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 0.71(19) . . . . ?
C12 C11 C16 C15 -0.30(18) . . . . ?
C1 C11 C16 C15 178.82(11) . . . . ?
C1 N1 C21 C26 -149.29(12) . . . . ?
C1 N1 C21 C22 32.81(18) . . . . ?
C26 C21 C22 C23 0.25(18) . . . . ?
N1 C21 C22 C23 178.10(11) . . . . ?
C21 C22 C23 F23 179.44(11) . . . . ?
C21 C22 C23 C24 -0.24(19) . . . . ?
F23 C23 C24 F24 -0.59(18) . . . . ?
C22 C23 C24 F24 179.09(11) . . . . ?
F23 C23 C24 C25 -179.53(12) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
F24 C24 C25 C26 -179.00(11) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C24 C25 C26 C21 0.10(19) . . . . ?
C22 C21 C26 C25 -0.19(18) . . . . ?
N1 C21 C26 C25 -178.13(11) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A      D-H...A   symm   publ
#   -    -    -     ---       -----     -----      -------   ----   ----
N1 H1 O1 0.843(16) 2.483(17) 3.2582(14) 153.3(14) 1_655 yes
C26 H26 O1 0.93 2.56 3.2489(15) 131.3 1_655 yes
C22 H22 O1 0.93 2.42 2.8939(15) 111.9 . yes

#
#    Crystals grown from CHCl3

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_34_F2_294K
_database_code_depnum_ccdc_archive 'CCDC 1453279'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(34_F2 or 10-019)'
_chemical_name_common            ?
_chemical_melting_point          470
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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                   5.4519(2)
_cell_length_b                   7.7415(5)
_cell_length_c                   12.9335(7)
_cell_angle_alpha                106.965(5)
_cell_angle_beta                 100.535(4)
_cell_angle_gamma                90.213(4)
_cell_volume                     512.37(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4601
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      27.1

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            7552
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.356
_diffrn_reflns_theta_max         27.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2183
_reflns_number_gt                1781
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0519P)²+0.0765P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2183
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033

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
F13 F 0.19057(17) -0.00943(13) 0.08354(7) 0.0578(3) Uani 1 1 d . . . . .
F14 F 0.57065(19) -0.21505(13) 0.03710(7) 0.0595(3) Uani 1 1 d . . . . .
O1 O 0.38282(18) 0.25821(16) 0.49546(8) 0.0514(3) Uani 1 1 d . . . . .
N1 N 0.8075(2) 0.28782(15) 0.53305(9) 0.0351(3) Uani 1 1 d . . . . .
H1 H 0.930(3) 0.278(2) 0.5032(13) 0.044(4) Uiso 1 1 d . . . . .
C1 C 0.5830(2) 0.22550(17) 0.46626(10) 0.0341(3) Uani 1 1 d . . . . .
C11 C 0.5942(2) 0.11163(16) 0.35204(10) 0.0315(3) Uani 1 1 d . . . . .
C12 C 0.3897(2) 0.10779(17) 0.26954(10) 0.0350(3) Uani 1 1 d . . . . .
H12 H 0.2560 0.1784 0.2854 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3868(2) -0.00093(19) 0.16451(11) 0.0383(3) Uani 1 1 d . . . . .
C14 C 0.5840(3) -0.10684(18) 0.14074(11) 0.0390(3) Uani 1 1 d . . . . .
C15 C 0.7865(3) -0.10561(19) 0.22085(11) 0.0404(3) Uani 1 1 d . . . . .
H15 H 0.9183 -0.1779 0.2042 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7926(2) 0.00469(18) 0.32699(11) 0.0363(3) Uani 1 1 d . . . . .
H16 H 0.9302 0.0074 0.3820 0.044 Uiso 1 1 calc R U . . .
C21 C 0.8515(2) 0.39187(16) 0.64532(10) 0.0312(3) Uani 1 1 d . . . . .
C22 C 0.6926(2) 0.37923(18) 0.71572(10) 0.0360(3) Uani 1 1 d . . . . .
H22 H 0.5464 0.3049 0.6890 0.043 Uiso 1 1 calc R U . . .
C23 C 0.7535(3) 0.47817(19) 0.82592(11) 0.0398(3) Uani 1 1 d . . . . .
H23 H 0.6469 0.4699 0.8730 0.048 Uiso 1 1 calc R U . . .
C24 C 0.9700(3) 0.58905(19) 0.86706(11) 0.0415(3) Uani 1 1 d . . . . .
H24 H 1.0093 0.6547 0.9413 0.050 Uiso 1 1 calc R U . . .
C25 C 1.1273(3) 0.60131(18) 0.79670(11) 0.0404(3) Uani 1 1 d . . . . .
H25 H 1.2733 0.6758 0.8237 0.048 Uiso 1 1 calc R U . . .
C26 C 1.0691(2) 0.50347(18) 0.68637(11) 0.0358(3) Uani 1 1 d . . . . .
H26 H 1.1759 0.5124 0.6395 0.043 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
F13 C13 1.3398(15) . ?
F14 C14 1.3462(15) . ?
O1 C1 1.2224(16) . ?
N1 C1 1.3578(16) . ?
N1 C21 1.4155(16) . ?
N1 H1 0.824(17) . ?
C1 C11 1.4956(17) . ?
C11 C12 1.3886(18) . ?
C11 C16 1.3926(18) . ?
C12 C13 1.3706(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(2) . ?
C14 C15 1.367(2) . ?
C15 C16 1.3833(18) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C22 1.3891(18) . ?
C21 C26 1.3892(18) . ?
C22 C23 1.3843(18) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.381(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.3829(19) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 N1 C21 127.20(11) . . ?
C1 N1 H1 116.6(11) . . ?
C21 N1 H1 115.4(11) . . ?
O1 C1 N1 123.50(12) . . ?
O1 C1 C11 121.09(11) . . ?
N1 C1 C11 115.41(11) . . ?
C12 C11 C16 119.58(11) . . ?
C12 C11 C1 117.36(11) . . ?
C16 C11 C1 122.99(11) . . ?
C13 C12 C11 119.42(12) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
F13 C13 C12 120.77(13) . . ?
F13 C13 C14 118.72(12) . . ?
C12 C13 C14 120.50(12) . . ?
F14 C14 C15 120.45(13) . . ?
F14 C14 C13 118.54(12) . . ?
C15 C14 C13 120.99(12) . . ?
C14 C15 C16 119.06(12) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 120.44(12) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C21 C26 119.62(11) . . ?
C22 C21 N1 122.48(11) . . ?
C26 C21 N1 117.83(11) . . ?
C23 C22 C21 119.44(12) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 121.09(12) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.25(12) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.38(12) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.22(12) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?

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
C21 N1 C1 O1 2.6(2) . . . . ?
C21 N1 C1 C11 -177.43(12) . . . . ?
O1 C1 C11 C12 26.46(19) . . . . ?
N1 C1 C11 C12 -153.54(12) . . . . ?
O1 C1 C11 C16 -150.34(14) . . . . ?
N1 C1 C11 C16 29.65(18) . . . . ?
C16 C11 C12 C13 -0.20(19) . . . . ?
C1 C11 C12 C13 -177.12(12) . . . . ?
C11 C12 C13 F13 179.04(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
F13 C13 C14 F14 -0.26(19) . . . . ?
C12 C13 C14 F14 178.35(12) . . . . ?
F13 C13 C14 C15 -178.79(12) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
F14 C14 C15 C16 -178.86(12) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C12 C11 C16 C15 -0.3(2) . . . . ?
C1 C11 C16 C15 176.40(12) . . . . ?
C1 N1 C21 C22 29.5(2) . . . . ?
C1 N1 C21 C26 -153.66(13) . . . . ?
C26 C21 C22 C23 -0.02(19) . . . . ?
N1 C21 C22 C23 176.74(12) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C24 C25 C26 C21 0.0(2) . . . . ?
C22 C21 C26 C25 0.07(19) . . . . ?
N1 C21 C26 C25 -176.84(12) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A      D-H...A   symm   publ
#   -    -    -     ---       -----     -----      -------   ----   ----
N1 H1 O1 0.824(17) 2.493(17) 3.2594(15) 155.3(15) 1_655 yes
C22 H22 O1 0.93 2.42 2.9182(16) 114 . yes
#   C26  H26  O1    0.93      2.69      3.3852(16) 132       1_655  yes

#   C15  H15  C21   0.93  3.02  3.5810(19)  120.5  2_756  no
#   C15  H15  C22   0.93  2.86  3.6651(19)  145.9  2_756  no
#   C15  H15  C23   0.93  2.92  3.816(2)    162.8  2_756  no
#   C15  H15  C24   0.93  3.14  3.895(2)    139.5  2_756  no
#   C15  H15  C25   0.93  3.28  3.813(2)    118.4  2_756  no
#   C15  H15  C26   0.93  3.23  3.657(2)    110.5  2_756  no

#   C12  H12  C21   0.93  3.27  4.0030(18)  137.4  2_666  no
#   C12  H12  C22   0.93  3.44  3.9511(19)  117.1  2_666  no
#   C12  H12  C23   0.93  3.37  3.7925(19)  110.2  2_666  no
#   C12  H12  C24   0.93  3.14  3.696(2)    120.4  2_666  no
#   C12  H12  C25   0.93  2.95  3.7473(19)  145.3  2_666  no
#   C12  H12  C26   0.93  3.01  3.9007(19)  159.9  2_666  no

#   C22  H22  C11   0.93  3.18  3.8939(18)  135.2  2_656  no
#   C22  H22  C12   0.93  3.40  3.8589(19)  113.0  2_656  no
#   C22  H22  C13   0.93  3.41  3.7478(19)  104.3  2_656  no
#   C22  H22  C14   0.93  3.20  3.6676(19)  113.2  2_656  no
#   C22  H22  C15   0.93  2.97  3.7064(19)  136.9  2_656  no
#   C22  H22  C16   0.93  2.96  3.8190(18)  154.8  2_656  no


#   Complete details for the three C-H...\p(arene) interactions
#
#    Crystals grown from n-hexane

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_F2_35_294K
_database_code_depnum_ccdc_archive 'CCDC 1453280'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(F2_35 or 11-035)'
_chemical_name_common            ?
_chemical_melting_point          419
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.3601(2)
_cell_length_b                   5.15750(10)
_cell_length_c                   20.2429(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.012(2)
_cell_angle_gamma                90
_cell_volume                     1053.85(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2833
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.95

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            6778
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.465
_diffrn_reflns_theta_max         27.012
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2266
_reflns_number_gt                1996
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'

_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)+(0.0398P)²+0.2321P] 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     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.0063(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029

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
F23 F 1.02981(9) 0.10438(19) -0.10378(5) 0.0672(3) Uani 1 1 d . . . . .
F25 F 0.78647(11) 0.83296(19) -0.19555(4) 0.0713(3) Uani 1 1 d . . . . .
O1 O 0.67864(10) 0.89705(16) 0.02080(5) 0.0496(3) Uani 1 1 d . . . . .
C1 C 0.67975(12) 0.6755(2) 0.04263(6) 0.0376(3) Uani 1 1 d . . . . .
N1 N 0.72635(11) 0.4702(2) 0.01319(5) 0.0418(3) Uani 1 1 d . . . . .
H1 H 0.7190(15) 0.321(3) 0.0288(8) 0.050(4) Uiso 1 1 d . . . . .
C11 C 0.62966(12) 0.6159(2) 0.10467(6) 0.0374(3) Uani 1 1 d . . . . .
C12 C 0.53340(13) 0.7780(3) 0.11942(7) 0.0461(3) Uani 1 1 d . . . . .
H12 H 0.5011 0.9150 0.0905 0.055 Uiso 1 1 calc R U . . .
C13 C 0.48505(15) 0.7372(3) 0.17698(7) 0.0541(3) Uani 1 1 d . . . . .
H13 H 0.4190 0.8443 0.1861 0.065 Uiso 1 1 calc R U . . .
C14 C 0.53436(15) 0.5391(3) 0.22050(7) 0.0539(4) Uani 1 1 d . . . . .
H14 H 0.5027 0.5138 0.2595 0.065 Uiso 1 1 calc R U . . .
C15 C 0.63037(16) 0.3779(3) 0.20662(7) 0.0555(4) Uani 1 1 d . . . . .
H15 H 0.6635 0.2437 0.2363 0.067 Uiso 1 1 calc R U . . .
C16 C 0.67812(14) 0.4144(3) 0.14856(7) 0.0484(3) Uani 1 1 d . . . . .
H16 H 0.7426 0.3039 0.1391 0.058 Uiso 1 1 calc R U . . .
C21 C 0.78766(12) 0.4792(2) -0.04243(6) 0.0376(3) Uani 1 1 d . . . . .
C22 C 0.87971(13) 0.2877(2) -0.04615(6) 0.0425(3) Uani 1 1 d . . . . .
H22 H 0.9007 0.1608 -0.0128 0.051 Uiso 1 1 calc R U . . .
C23 C 0.93902(13) 0.2905(3) -0.10036(7) 0.0455(3) Uani 1 1 d . . . . .
C24 C 0.91168(14) 0.4710(3) -0.15121(7) 0.0489(3) Uani 1 1 d . . . . .
H24 H 0.9535 0.4693 -0.1873 0.059 Uiso 1 1 calc R U . . .
C25 C 0.81933(14) 0.6534(3) -0.14567(6) 0.0473(3) Uani 1 1 d . . . . .
C26 C 0.75630(13) 0.6660(2) -0.09271(6) 0.0445(3) Uani 1 1 d . . . . .
H26 H 0.6948 0.7955 -0.0907 0.053 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
F23 C23 1.3567(15) . ?
F25 C25 1.3557(15) . ?
O1 C1 1.2244(14) . ?
C1 N1 1.3558(15) . ?
C1 C11 1.4948(16) . ?
N1 C21 1.4126(15) . ?
N1 H1 0.843(16) . ?
C11 C12 1.3845(17) . ?
C11 C16 1.3858(17) . ?
C12 C13 1.3841(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3868(19) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.3860(17) . ?
C21 C22 1.3865(17) . ?
C22 C23 1.3732(17) . ?
C22 H22 0.9300 . ?
C23 C24 1.3692(19) . ?
C24 C25 1.3644(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.3768(18) . ?
C26 H26 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
O1 C1 N1 123.05(11) . . ?
O1 C1 C11 121.21(10) . . ?
N1 C1 C11 115.73(10) . . ?
C1 N1 C21 126.40(10) . . ?
C1 N1 H1 118.5(10) . . ?
C21 N1 H1 115.1(10) . . ?
C12 C11 C16 119.28(11) . . ?
C12 C11 C1 117.41(11) . . ?
C16 C11 C1 123.27(11) . . ?
C13 C12 C11 120.30(12) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.09(13) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.15(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.28(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 119.89(13) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C26 C21 C22 120.38(11) . . ?
C26 C21 N1 122.33(11) . . ?
C22 C21 N1 117.27(10) . . ?
C23 C22 C21 118.21(11) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
F23 C23 C24 118.10(12) . . ?
F23 C23 C22 118.26(12) . . ?
C24 C23 C22 123.64(12) . . ?
C25 C24 C23 115.92(12) . . ?
C25 C24 H24 122.0 . . ?
C23 C24 H24 122.0 . . ?
F25 C25 C24 118.23(11) . . ?
F25 C25 C26 117.66(12) . . ?
C24 C25 C26 124.12(12) . . ?
C25 C26 C21 117.72(12) . . ?
C25 C26 H26 121.1 . . ?
C21 C26 H26 121.1 . . ?

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
O1 C1 N1 C21 4.7(2) . . . . ?
C11 C1 N1 C21 -174.91(11) . . . . ?
O1 C1 C11 C12 27.58(18) . . . . ?
N1 C1 C11 C12 -152.83(12) . . . . ?
O1 C1 C11 C16 -150.05(13) . . . . ?
N1 C1 C11 C16 29.54(17) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C1 C11 C12 C13 -178.49(12) . . . . ?
C11 C12 C13 C14 1.4(2) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C1 C11 C16 C15 177.35(12) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C1 N1 C21 C26 -30.62(19) . . . . ?
C1 N1 C21 C22 150.93(12) . . . . ?
C26 C21 C22 C23 0.55(18) . . . . ?
N1 C21 C22 C23 179.04(11) . . . . ?
C21 C22 C23 F23 179.53(11) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
F23 C23 C24 C25 179.72(12) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 F25 -178.50(12) . . . . ?
C23 C24 C25 C26 1.0(2) . . . . ?
F25 C25 C26 C21 178.61(12) . . . . ?
C24 C25 C26 C21 -0.9(2) . . . . ?
C22 C21 C26 C25 0.07(19) . . . . ?
N1 C21 C26 C25 -178.33(12) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A      D-H...A   symm   publ
#   -    -    -     ---       -----     -----      -------   ----   ----
N1 H1 O1 0.843(16) 2.225(16) 3.0069(13) 154.5(14) 1_545 yes
C26 H26 O1 0.93 2.36 2.8598(15) 113 . yes

#
#    Crystals grown from CHCl3

#=====================================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_35_F2_294K
_database_code_depnum_ccdc_archive 'CCDC 1453281'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(35_F2 or 10-021)'
_chemical_name_common            ?
_chemical_melting_point          412
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   5.10950(10)
_cell_length_b                   9.4583(4)
_cell_length_c                   22.2306(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.284(3)
_cell_angle_gamma                90
_cell_volume                     1067.89(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1760
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      26.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            6521
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.506
_diffrn_reflns_theta_max         26.939
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.730
_diffrn_reflns_point_group_measured_fraction_full 0.751
_reflns_number_total             3400
_reflns_number_gt                1894
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.490
_reflns_Friedel_fraction_max     0.481
_reflns_Friedel_fraction_full    0.507

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_refine_special_details          
'Two disordered molecules treated using SHELXL14/7'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²] 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_abs_structure_details 
;
Flack x from 491 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   2.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3400
_refine_ls_number_parameters     411
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_restrained_S_all      0.869
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.025

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
F13A F 1.2728(11) 0.5088(6) 0.4006(3) 0.0797(13) Uani 0.78 1 d . . P A 1
F15A F 0.5781(8) 0.8133(5) 0.42865(18) 0.0668(11) Uani 0.78 1 d . . P A 1
O1A O 1.2248(8) 0.8456(6) 0.2274(2) 0.0554(13) Uani 0.78 1 d . . P A 1
N1A N 0.7953(12) 0.8978(8) 0.2116(3) 0.0517(18) Uani 0.78 1 d . . P A 1
H1A H 0.6486 0.8894 0.2269 0.062 Uiso 0.78 1 calc R U P A 1
C1A C 1.0034(19) 0.8457(13) 0.2438(4) 0.049(2) Uani 0.78 1 d . . P A 1
C11A C 0.9575(19) 0.7709(12) 0.3024(4) 0.051(2) Uani 0.78 1 d . . P A 1
C12A C 1.122(2) 0.6628(11) 0.3240(4) 0.052(3) Uani 0.78 1 d . . P A 1
H12A H 1.2448 0.6249 0.3006 0.062 Uiso 0.78 1 calc R U P A 1
C13A C 1.0984(17) 0.6113(10) 0.3824(3) 0.047(2) Uani 0.78 1 d . . P A 1
C14A C 0.9151(19) 0.6612(10) 0.4172(4) 0.058(3) Uani 0.78 1 d . . P A 1
H14A H 0.8986 0.6240 0.4554 0.070 Uiso 0.78 1 calc R U P A 1
C15A C 0.7576(15) 0.7678(10) 0.3936(4) 0.054(2) Uani 0.78 1 d . . P A 1
C16A C 0.7735(16) 0.8286(10) 0.3371(4) 0.050(2) Uani 0.78 1 d . . P A 1
H16A H 0.6666 0.9040 0.3233 0.060 Uiso 0.78 1 calc R U P A 1
C21A C 0.7828(17) 0.9652(10) 0.1557(4) 0.049(2) Uani 0.78 1 d . . P A 1
C22A C 0.5895(19) 1.0684(12) 0.1429(5) 0.061(3) Uani 0.78 1 d . . P A 1
H22A H 0.4730 1.0881 0.1711 0.073 Uiso 0.78 1 calc R U P A 1
C23A C 0.570(3) 1.1358(14) 0.0931(6) 0.083(3) Uani 0.78 1 d . . P A 1
H23A H 0.4486 1.2089 0.0875 0.099 Uiso 0.78 1 calc R U P A 1
C24A C 0.726(3) 1.1048(15) 0.0453(5) 0.075(3) Uani 0.78 1 d . . P A 1
H24A H 0.7038 1.1513 0.0083 0.090 Uiso 0.78 1 calc R U P A 1
C25A C 0.913(2) 1.0012(16) 0.0582(4) 0.071(3) Uani 0.78 1 d . . P A 1
H25A H 1.0185 0.9758 0.0285 0.085 Uiso 0.78 1 calc R U P A 1
C26A C 0.9475(18) 0.9359(11) 0.1113(3) 0.058(3) Uani 0.78 1 d . . P A 1
H26A H 1.0826 0.8703 0.1189 0.070 Uiso 0.78 1 calc R U P A 1
F13C F 1.073(6) 0.953(4) 0.0218(13) 0.175(13) Uani 0.22 1 d . U P B 2
F15C F 0.408(4) 1.246(2) 0.0602(9) 0.092(5) Uani 0.22 1 d . U P B 2
O1C O 0.466(5) 0.894(4) 0.2318(15) 0.153(13) Uani 0.22 1 d D U P B 2
N1C N 0.909(6) 0.844(4) 0.2485(13) 0.102(14) Uani 0.22 1 d D U P B 2
H1C H 1.0485 0.8363 0.2305 0.123 Uiso 0.22 1 calc R U P B 2
C1C C 0.709(5) 0.911(3) 0.2171(11) 0.038(2) Uiso 0.22 1 d D U P B 2
C11C C 0.743(5) 0.993(3) 0.1601(8) 0.038(2) Uiso 0.22 1 d DG U P B 2
C12C C 0.549(5) 1.090(3) 0.1396(11) 0.038(2) Uiso 0.22 1 d DG U P B 2
H12C H 0.4170 1.1133 0.1635 0.046 Uiso 0.22 1 calc R U P B 2
C13C C 0.553(6) 1.153(3) 0.0832(11) 0.038(2) Uiso 0.22 1 d G U P B 2
C14C C 0.751(6) 1.119(3) 0.0474(9) 0.038(2) Uiso 0.22 1 d G U P B 2
H14C H 0.7533 1.1612 0.0096 0.046 Uiso 0.22 1 calc R U P B 2
C15C C 0.944(5) 1.022(3) 0.0679(9) 0.038(2) Uiso 0.22 1 d G U P B 2
C16C C 0.940(4) 0.959(2) 0.1243(9) 0.038(2) Uiso 0.22 1 d DG U P B 2
H16C H 1.0694 0.8939 0.1381 0.046 Uiso 0.22 1 calc R U P B 2
C21C C 0.924(6) 0.786(3) 0.3059(11) 0.038(2) Uiso 0.22 1 d DG U P B 2
C22C C 1.131(5) 0.692(3) 0.3195(12) 0.038(2) Uiso 0.22 1 d G U P B 2
H22C H 1.2599 0.6825 0.2933 0.046 Uiso 0.22 1 calc R U P B 2
C23C C 1.145(4) 0.612(2) 0.3721(12) 0.038(2) Uiso 0.22 1 d G U P B 2
H23C H 1.2836 0.5488 0.3812 0.046 Uiso 0.22 1 calc R U P B 2
C24C C 0.952(5) 0.626(2) 0.4113(9) 0.038(2) Uiso 0.22 1 d G U P B 2
H24C H 0.9619 0.5723 0.4465 0.046 Uiso 0.22 1 calc R U P B 2
C25C C 0.746(4) 0.720(2) 0.3978(11) 0.038(2) Uiso 0.22 1 d G U P B 2
H25C H 0.6166 0.7295 0.4239 0.046 Uiso 0.22 1 calc R U P B 2
C26C C 0.731(4) 0.800(2) 0.3451(13) 0.038(2) Uiso 0.22 1 d G U P B 2
H26C H 0.5930 0.8633 0.3360 0.046 Uiso 0.22 1 calc R U P B 2
F13B F 0.4097(9) 0.7452(5) 0.06295(19) 0.0751(11) Uani 0.85 1 d . . P C 1
F15B F 1.1074(9) 0.4430(6) 0.0341(2) 0.0869(15) Uani 0.85 1 d . . P C 1
O1B O 0.4683(8) 0.4049(6) 0.2364(2) 0.0655(14) Uani 0.85 1 d . . P C 1
N1B N 0.9014(9) 0.3544(7) 0.2517(3) 0.0538(15) Uani 0.85 1 d . . P C 1
H1B H 1.0484 0.3629 0.2365 0.065 Uiso 0.85 1 calc R U P C 1
C1B C 0.6909(13) 0.4126(8) 0.2206(3) 0.0489(18) Uani 0.85 1 d . . P C 1
C11B C 0.7281(12) 0.4756(9) 0.1606(3) 0.0451(18) Uani 0.85 1 d . . P C 1
C12B C 0.5551(14) 0.5809(9) 0.1390(3) 0.0462(19) Uani 0.85 1 d . . P C 1
H12B H 0.4240 0.6125 0.1617 0.055 Uiso 0.85 1 calc R U P C 1
C13B C 0.5811(19) 0.6348(10) 0.0857(4) 0.063(2) Uani 0.85 1 d . . P C 1
C14B C 0.7616(16) 0.5924(9) 0.0467(3) 0.051(2) Uani 0.85 1 d . . P C 1
H14B H 0.7678 0.6308 0.0083 0.061 Uiso 0.85 1 calc R U P C 1
C15B C 0.9279(14) 0.4893(9) 0.0703(3) 0.0508(19) Uani 0.85 1 d . . P C 1
C16B C 0.9187(13) 0.4308(9) 0.1256(3) 0.052(2) Uani 0.85 1 d . . P C 1
H16B H 1.0391 0.3615 0.1397 0.062 Uiso 0.85 1 calc R U P C 1
C21B C 0.9085(15) 0.2782(10) 0.3086(3) 0.051(2) Uani 0.85 1 d . . P C 1
C22B C 1.1003(17) 0.1769(11) 0.3192(4) 0.064(3) Uani 0.85 1 d . . P C 1
H22B H 1.2096 0.1544 0.2898 0.077 Uiso 0.85 1 calc R U P C 1
C23B C 1.129(2) 0.1066(10) 0.3767(4) 0.066(3) Uani 0.85 1 d . . P C 1
H23B H 1.2597 0.0391 0.3854 0.079 Uiso 0.85 1 calc R U P C 1
C24B C 0.970(2) 0.1377(11) 0.4166(5) 0.076(3) Uani 0.85 1 d . . P C 1
H24B H 0.9883 0.0907 0.4536 0.091 Uiso 0.85 1 calc R U P C 1
C25B C 0.7764(17) 0.2374(13) 0.4061(4) 0.070(3) Uani 0.85 1 d . . P C 1
H25B H 0.6657 0.2560 0.4357 0.084 Uiso 0.85 1 calc R U P C 1
C26B C 0.7430(17) 0.3114(11) 0.3517(3) 0.062(2) Uani 0.85 1 d . . P C 1
H26B H 0.6139 0.3806 0.3446 0.075 Uiso 0.85 1 calc R U P C 1
F13D F 1.286(7) 0.026(3) 0.3683(19) 0.176(16) Uani 0.15 1 d . U P D 2
F15D F 0.574(5) 0.305(3) 0.4263(12) 0.072(6) Uani 0.15 1 d . U P D 2
O1D O 1.230(6) 0.340(5) 0.2223(17) 0.115(13) Uani 0.15 1 d D U P D 2
N1D N 0.806(7) 0.413(4) 0.2031(12) 0.091(14) Uani 0.15 1 d D U P D 2
H1D H 0.6543 0.3862 0.2119 0.109 Uiso 0.15 1 calc R U P D 2
C1D C 1.004(5) 0.365(3) 0.2419(11) 0.038(4) Uiso 0.15 1 d D U P D 2
C11D C 0.948(6) 0.291(4) 0.3003(12) 0.038(4) Uiso 0.15 1 d DG U P D 2
C12D C 1.146(5) 0.199(4) 0.3237(14) 0.038(4) Uiso 0.15 1 d DG U P D 2
H12D H 1.2826 0.1765 0.3009 0.046 Uiso 0.15 1 calc R U P D 2
C13D C 1.141(6) 0.141(3) 0.3810(14) 0.038(4) Uiso 0.15 1 d G U P D 2
C14D C 0.937(7) 0.175(4) 0.4150(11) 0.038(4) Uiso 0.15 1 d G U P D 2
H14D H 0.9334 0.1367 0.4534 0.046 Uiso 0.15 1 calc R U P D 2
C15D C 0.738(6) 0.267(4) 0.3917(12) 0.038(4) Uiso 0.15 1 d G U P D 2
C16D C 0.744(5) 0.324(4) 0.3343(13) 0.038(4) Uiso 0.15 1 d DG U P D 2
H16D H 0.6108 0.3857 0.3187 0.046 Uiso 0.15 1 calc R U P D 2
C21D C 0.794(5) 0.496(3) 0.1519(10) 0.038(4) Uiso 0.15 1 d DG U P D 2
C22D C 0.606(6) 0.602(4) 0.1412(12) 0.038(4) Uiso 0.15 1 d G U P D 2
H22D H 0.5070 0.6299 0.1719 0.046 Uiso 0.15 1 calc R U P D 2
C23D C 0.566(7) 0.666(3) 0.0847(15) 0.038(4) Uiso 0.15 1 d G U P D 2
H23D H 0.4399 0.7370 0.0776 0.046 Uiso 0.15 1 calc R U P D 2
C24D C 0.713(7) 0.624(4) 0.0389(11) 0.038(4) Uiso 0.15 1 d G U P D 2
H24D H 0.6866 0.6673 0.0011 0.046 Uiso 0.15 1 calc R U P D 2
C25D C 0.901(5) 0.519(3) 0.0496(10) 0.038(4) Uiso 0.15 1 d G U P D 2
H25D H 1.0004 0.4906 0.0189 0.046 Uiso 0.15 1 calc R U P D 2
C26D C 0.942(5) 0.454(3) 0.1061(13) 0.038(4) Uiso 0.15 1 d G U P D 2
H26D H 1.0675 0.3836 0.1133 0.046 Uiso 0.15 1 calc R U P D 2


_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
F13A C13A 1.348(10) . ?
F15A C15A 1.338(9) . ?
O1A C1A 1.226(10) . ?
N1A C1A 1.311(10) . ?
N1A C21A 1.392(10) . ?
N1A H1A 0.8600 . ?
C1A C11A 1.523(13) . ?
C11A C12A 1.376(13) . ?
C11A C16A 1.392(10) . ?
C12A C13A 1.404(11) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.363(11) . ?
C14A C15A 1.360(13) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.392(11) . ?
C16A H16A 0.9300 . ?
C21A C26A 1.393(10) . ?
C21A C22A 1.396(11) . ?
C22A C23A 1.273(13) . ?
C22A H22A 0.9300 . ?
C23A C24A 1.425(12) . ?
C23A H23A 0.9300 . ?
C24A C25A 1.374(14) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.326(12) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
F13C C15C 1.43(3) . ?
F15C C13C 1.22(3) . ?
O1C C1C 1.33(2) . ?
N1C C1C 1.33(2) . ?
N1C C21C 1.38(2) . ?
N1C H1C 0.8600 . ?
C1C C11C 1.513(17) . ?
C11C C12C 1.3900 . ?
C11C C16C 1.3900 . ?
C12C C13C 1.3900 . ?
C12C H12C 0.9300 . ?
C13C C14C 1.3900 . ?
C14C C15C 1.3900 . ?
C14C H14C 0.9300 . ?
C15C C16C 1.3900 . ?
C16C H16C 0.9300 . ?
C21C C22C 1.3900 . ?
C21C C26C 1.3900 . ?
C22C C23C 1.3900 . ?
C22C H22C 0.9300 . ?
C23C C24C 1.3900 . ?
C23C H23C 0.9300 . ?
C24C C25C 1.3900 . ?
C24C H24C 0.9300 . ?
C25C C26C 1.3900 . ?
C25C H25C 0.9300 . ?
C26C H26C 0.9300 . ?
F13B C13B 1.420(9) . ?
F15B C15B 1.357(8) . ?
O1B C1B 1.229(7) . ?
N1B C1B 1.332(7) . ?
N1B C21B 1.452(10) . ?
N1B H1B 0.8600 . ?
C1B C11B 1.490(10) . ?
C11B C16B 1.379(9) . ?
C11B C12B 1.382(11) . ?
C12B C13B 1.309(11) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.393(10) . ?
C14B C15B 1.361(11) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.354(9) . ?
C16B H16B 0.9300 . ?
C21B C22B 1.372(12) . ?
C21B C26B 1.382(10) . ?
C22B C23B 1.433(12) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.301(11) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.367(12) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.392(11) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
F13D C13D 1.36(4) . ?
F15D C15D 1.25(3) . ?
O1D C1D 1.30(2) . ?
N1D C1D 1.33(2) . ?
N1D C21D 1.38(2) . ?
N1D H1D 0.8600 . ?
C1D C11D 1.532(17) . ?
C11D C12D 1.3900 . ?
C11D C16D 1.3900 . ?
C12D C13D 1.3900 . ?
C12D H12D 0.9300 . ?
C13D C14D 1.3900 . ?
C14D C15D 1.3900 . ?
C14D H14D 0.9300 . ?
C15D C16D 1.3900 . ?
C16D H16D 0.9300 . ?
C21D C22D 1.3900 . ?
C21D C26D 1.3900 . ?
C22D C23D 1.3900 . ?
C22D H22D 0.9300 . ?
C23D C24D 1.3900 . ?
C23D H23D 0.9300 . ?
C24D C25D 1.3900 . ?
C24D H24D 0.9300 . ?
C25D C26D 1.3900 . ?
C25D H25D 0.9300 . ?
C26D H26D 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
C1A N1A C21A 127.9(7) . . ?
C1A N1A H1A 116.0 . . ?
C21A N1A H1A 116.0 . . ?
O1A C1A N1A 123.9(8) . . ?
O1A C1A C11A 119.2(8) . . ?
N1A C1A C11A 116.7(8) . . ?
C12A C11A C16A 121.4(8) . . ?
C12A C11A C1A 119.9(8) . . ?
C16A C11A C1A 118.0(9) . . ?
C11A C12A C13A 118.0(7) . . ?
C11A C12A H12A 121.0 . . ?
C13A C12A H12A 121.0 . . ?
F13A C13A C14A 123.4(7) . . ?
F13A C13A C12A 114.0(7) . . ?
C14A C13A C12A 122.6(8) . . ?
C15A C14A C13A 116.8(7) . . ?
C15A C14A H14A 121.6 . . ?
C13A C14A H14A 121.6 . . ?
F15A C15A C14A 115.4(8) . . ?
F15A C15A C16A 120.3(8) . . ?
C14A C15A C16A 124.4(8) . . ?
C11A C16A C15A 116.6(8) . . ?
C11A C16A H16A 121.7 . . ?
C15A C16A H16A 121.7 . . ?
N1A C21A C26A 124.7(8) . . ?
N1A C21A C22A 117.7(7) . . ?
C26A C21A C22A 117.6(7) . . ?
C23A C22A C21A 120.8(8) . . ?
C23A C22A H22A 119.6 . . ?
C21A C22A H22A 119.6 . . ?
C22A C23A C24A 123.3(9) . . ?
C22A C23A H23A 118.3 . . ?
C24A C23A H23A 118.3 . . ?
C25A C24A C23A 115.0(8) . . ?
C25A C24A H24A 122.5 . . ?
C23A C24A H24A 122.5 . . ?
C26A C25A C24A 122.7(8) . . ?
C26A C25A H25A 118.7 . . ?
C24A C25A H25A 118.7 . . ?
C25A C26A C21A 120.3(8) . . ?
C25A C26A H26A 119.8 . . ?
C21A C26A H26A 119.8 . . ?
C1C N1C C21C 129(3) . . ?
C1C N1C H1C 115.3 . . ?
C21C N1C H1C 115.3 . . ?
O1C C1C N1C 120(2) . . ?
O1C C1C C11C 117.5(18) . . ?
N1C C1C C11C 122.2(18) . . ?
C12C C11C C16C 120.0 . . ?
C12C C11C C1C 118.4(14) . . ?
C16C C11C C1C 121.0(14) . . ?
C13C C12C C11C 120.0 . . ?
C13C C12C H12C 120.0 . . ?
C11C C12C H12C 120.0 . . ?
F15C C13C C12C 128(2) . . ?
F15C C13C C14C 112(2) . . ?
C12C C13C C14C 120.0 . . ?
C15C C14C C13C 120.0 . . ?
C15C C14C H14C 120.0 . . ?
C13C C14C H14C 120.0 . . ?
C14C C15C C16C 120.0 . . ?
C14C C15C F13C 115.4(19) . . ?
C16C C15C F13C 120(2) . . ?
C15C C16C C11C 120.0 . . ?
C15C C16C H16C 120.0 . . ?
C11C C16C H16C 120.0 . . ?
N1C C21C C22C 115(2) . . ?
N1C C21C C26C 124(2) . . ?
C22C C21C C26C 120.0 . . ?
C23C C22C C21C 120.0 . . ?
C23C C22C H22C 120.0 . . ?
C21C C22C H22C 120.0 . . ?
C22C C23C C24C 120.0 . . ?
C22C C23C H23C 120.0 . . ?
C24C C23C H23C 120.0 . . ?
C25C C24C C23C 120.0 . . ?
C25C C24C H24C 120.0 . . ?
C23C C24C H24C 120.0 . . ?
C26C C25C C24C 120.0 . . ?
C26C C25C H25C 120.0 . . ?
C24C C25C H25C 120.0 . . ?
C25C C26C C21C 120.0 . . ?
C25C C26C H26C 120.0 . . ?
C21C C26C H26C 120.0 . . ?
C1B N1B C21B 126.8(6) . . ?
C1B N1B H1B 116.6 . . ?
C21B N1B H1B 116.6 . . ?
O1B C1B N1B 123.1(6) . . ?
O1B C1B C11B 119.5(6) . . ?
N1B C1B C11B 117.1(6) . . ?
C16B C11B C12B 119.3(7) . . ?
C16B C11B C1B 123.3(7) . . ?
C12B C11B C1B 117.4(6) . . ?
C13B C12B C11B 118.1(7) . . ?
C13B C12B H12B 121.0 . . ?
C11B C12B H12B 121.0 . . ?
C12B C13B C14B 126.3(8) . . ?
C12B C13B F13B 119.3(8) . . ?
C14B C13B F13B 114.4(8) . . ?
C15B C14B C13B 113.2(6) . . ?
C15B C14B H14B 123.4 . . ?
C13B C14B H14B 123.4 . . ?
C16B C15B F15B 119.9(7) . . ?
C16B C15B C14B 124.1(7) . . ?
F15B C15B C14B 115.9(7) . . ?
C15B C16B C11B 119.0(7) . . ?
C15B C16B H16B 120.5 . . ?
C11B C16B H16B 120.5 . . ?
C22B C21B C26B 121.2(7) . . ?
C22B C21B N1B 116.5(7) . . ?
C26B C21B N1B 122.1(8) . . ?
C21B C22B C23B 118.6(7) . . ?
C21B C22B H22B 120.7 . . ?
C23B C22B H22B 120.7 . . ?
C24B C23B C22B 119.5(8) . . ?
C24B C23B H23B 120.2 . . ?
C22B C23B H23B 120.2 . . ?
C23B C24B C25B 122.2(8) . . ?
C23B C24B H24B 118.9 . . ?
C25B C24B H24B 118.9 . . ?
C24B C25B C26B 120.9(8) . . ?
C24B C25B H25B 119.6 . . ?
C26B C25B H25B 119.6 . . ?
C21B C26B C25B 117.5(8) . . ?
C21B C26B H26B 121.2 . . ?
C25B C26B H26B 121.2 . . ?
C1D N1D C21D 134(3) . . ?
C1D N1D H1D 113.1 . . ?
C21D N1D H1D 113.1 . . ?
O1D C1D N1D 119(2) . . ?
O1D C1D C11D 117(2) . . ?
N1D C1D C11D 120(2) . . ?
C12D C11D C16D 120.0 . . ?
C12D C11D C1D 114.0(16) . . ?
C16D C11D C1D 125.2(16) . . ?
C13D C12D C11D 120.0 . . ?
C13D C12D H12D 120.0 . . ?
C11D C12D H12D 120.0 . . ?
F13D C13D C12D 93(3) . . ?
F13D C13D C14D 139(3) . . ?
C12D C13D C14D 120.0 . . ?
C13D C14D C15D 120.0 . . ?
C13D C14D H14D 120.0 . . ?
C15D C14D H14D 120.0 . . ?
F15D C15D C16D 122(2) . . ?
F15D C15D C14D 118(2) . . ?
C16D C15D C14D 120.0 . . ?
C15D C16D C11D 120.0 . . ?
C15D C16D H16D 120.0 . . ?
C11D C16D H16D 120.0 . . ?
N1D C21D C22D 121(2) . . ?
N1D C21D C26D 118(2) . . ?
C22D C21D C26D 120.0 . . ?
C23D C22D C21D 120.0 . . ?
C23D C22D H22D 120.0 . . ?
C21D C22D H22D 120.0 . . ?
C22D C23D C24D 120.0 . . ?
C22D C23D H23D 120.0 . . ?
C24D C23D H23D 120.0 . . ?
C25D C24D C23D 120.0 . . ?
C25D C24D H24D 120.0 . . ?
C23D C24D H24D 120.0 . . ?
C24D C25D C26D 120.0 . . ?
C24D C25D H25D 120.0 . . ?
C26D C25D H25D 120.0 . . ?
C25D C26D C21D 120.0 . . ?
C25D C26D H26D 120.0 . . ?
C21D C26D H26D 120.0 . . ?

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
C21A N1A C1A O1A -2(2) . . . . ?
C21A N1A C1A C11A -177.2(9) . . . . ?
O1A C1A C11A C12A -24.7(16) . . . . ?
N1A C1A C11A C12A 150.4(11) . . . . ?
O1A C1A C11A C16A 145.8(10) . . . . ?
N1A C1A C11A C16A -39.1(16) . . . . ?
C16A C11A C12A C13A 0.2(13) . . . . ?
C1A C11A C12A C13A 170.4(10) . . . . ?
C11A C12A C13A F13A -177.9(9) . . . . ?
C11A C12A C13A C14A 2.1(13) . . . . ?
F13A C13A C14A C15A 178.0(9) . . . . ?
C12A C13A C14A C15A -2.0(13) . . . . ?
C13A C14A C15A F15A 179.3(8) . . . . ?
C13A C14A C15A C16A -0.5(13) . . . . ?
C12A C11A C16A C15A -2.4(12) . . . . ?
C1A C11A C16A C15A -172.8(9) . . . . ?
F15A C15A C16A C11A -177.2(8) . . . . ?
C14A C15A C16A C11A 2.6(12) . . . . ?
C1A N1A C21A C26A 31.2(17) . . . . ?
C1A N1A C21A C22A -149.6(12) . . . . ?
N1A C21A C22A C23A 178.7(11) . . . . ?
C26A C21A C22A C23A -2.0(14) . . . . ?
C21A C22A C23A C24A 5.1(15) . . . . ?
C22A C23A C24A C25A -3.7(14) . . . . ?
C23A C24A C25A C26A -0.8(15) . . . . ?
C24A C25A C26A C21A 3.7(15) . . . . ?
N1A C21A C26A C25A 176.9(10) . . . . ?
C22A C21A C26A C25A -2.4(13) . . . . ?
C21C N1C C1C O1C -19(7) . . . . ?
C21C N1C C1C C11C 167(4) . . . . ?
O1C C1C C11C C12C 24(4) . . . . ?
N1C C1C C11C C12C -162(3) . . . . ?
O1C C1C C11C C16C -146(3) . . . . ?
N1C C1C C11C C16C 27(5) . . . . ?
C16C C11C C12C C13C 0.0 . . . . ?
C1C C11C C12C C13C -171(3) . . . . ?
C11C C12C C13C F15C -175(3) . . . . ?
C11C C12C C13C C14C 0.0 . . . . ?
F15C C13C C14C C15C 176(3) . . . . ?
C12C C13C C14C C15C 0.0 . . . . ?
C13C C14C C15C C16C 0.0 . . . . ?
C13C C14C C15C F13C 157(3) . . . . ?
C14C C15C C16C C11C 0.0 . . . . ?
F13C C15C C16C C11C -156(3) . . . . ?
C12C C11C C16C C15C 0.0 . . . . ?
C1C C11C C16C C15C 171(3) . . . . ?
C1C N1C C21C C22C 163(4) . . . . ?
C1C N1C C21C C26C -7(7) . . . . ?
N1C C21C C22C C23C -171(3) . . . . ?
C26C C21C C22C C23C 0.0 . . . . ?
C21C C22C C23C C24C 0.0 . . . . ?
C22C C23C C24C C25C 0.0 . . . . ?
C23C C24C C25C C26C 0.0 . . . . ?
C24C C25C C26C C21C 0.0 . . . . ?
N1C C21C C26C C25C 170(4) . . . . ?
C22C C21C C26C C25C 0.0 . . . . ?
C21B N1B C1B O1B -1.9(13) . . . . ?
C21B N1B C1B C11B -175.2(9) . . . . ?
O1B C1B C11B C16B -146.5(8) . . . . ?
N1B C1B C11B C16B 27.0(11) . . . . ?
O1B C1B C11B C12B 31.3(11) . . . . ?
N1B C1B C11B C12B -155.2(7) . . . . ?
C16B C11B C12B C13B -0.4(12) . . . . ?
C1B C11B C12B C13B -178.3(8) . . . . ?
C11B C12B C13B C14B 2.8(13) . . . . ?
C11B C12B C13B F13B -178.7(8) . . . . ?
C12B C13B C14B C15B -3.1(13) . . . . ?
F13B C13B C14B C15B 178.3(8) . . . . ?
C13B C14B C15B C16B 1.1(11) . . . . ?
C13B C14B C15B F15B 179.6(7) . . . . ?
F15B C15B C16B C11B -177.4(7) . . . . ?
C14B C15B C16B C11B 0.9(12) . . . . ?
C12B C11B C16B C15B -1.3(11) . . . . ?
C1B C11B C16B C15B 176.4(7) . . . . ?
C1B N1B C21B C22B 151.7(8) . . . . ?
C1B N1B C21B C26B -32.4(12) . . . . ?
C26B C21B C22B C23B -0.8(13) . . . . ?
N1B C21B C22B C23B 175.2(8) . . . . ?
C21B C22B C23B C24B 1.5(13) . . . . ?
C22B C23B C24B C25B -0.8(14) . . . . ?
C23B C24B C25B C26B -0.6(15) . . . . ?
C22B C21B C26B C25B -0.6(13) . . . . ?
N1B C21B C26B C25B -176.3(9) . . . . ?
C24B C25B C26B C21B 1.3(13) . . . . ?
C21D N1D C1D O1D -31(7) . . . . ?
C21D N1D C1D C11D 171(4) . . . . ?
O1D C1D C11D C12D -3(4) . . . . ?
N1D C1D C11D C12D 155(3) . . . . ?
O1D C1D C11D C16D 167(3) . . . . ?
N1D C1D C11D C16D -35(5) . . . . ?
C16D C11D C12D C13D 0.0 . . . . ?
C1D C11D C12D C13D 170(3) . . . . ?
C11D C12D C13D F13D 155(3) . . . . ?
C11D C12D C13D C14D 0.0 . . . . ?
F13D C13D C14D C15D -140(4) . . . . ?
C12D C13D C14D C15D 0.0 . . . . ?
C13D C14D C15D F15D -173(3) . . . . ?
C13D C14D C15D C16D 0.0 . . . . ?
F15D C15D C16D C11D 172(4) . . . . ?
C14D C15D C16D C11D 0.0 . . . . ?
C12D C11D C16D C15D 0.0 . . . . ?
C1D C11D C16D C15D -169(4) . . . . ?
C1D N1D C21D C22D -138(4) . . . . ?
C1D N1D C21D C26D 54(5) . . . . ?
N1D C21D C22D C23D -168(3) . . . . ?
C26D C21D C22D C23D 0.0 . . . . ?
C21D C22D C23D C24D 0.0 . . . . ?
C22D C23D C24D C25D 0.0 . . . . ?
C23D C24D C25D C26D 0.0 . . . . ?
C24D C25D C26D C21D 0.0 . . . . ?
N1D C21D C26D C25D 169(3) . . . . ?
C22D C21D C26D C25D 0.0 . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A O1A 0.86 2.21 3.015(6) 157 1_455 yes
N1B H1B O1B 0.86 2.18 2.992(6) 157 1_655 yes
N1C H1C O1C 0.86 2.20 2.95(3) 146 1_655 yes
N1D H1D O1D 0.86 2.25 3.10(4) 171 1_455 yes

#
#    Crystals grown from n-hexane

#=====================================================================



#=====================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
