# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_wangqiang0312
_database_code_depnum_ccdc_archive 'CCDC 1407786'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_audit_creation_date             2015-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H15 F3 N4'
_chemical_formula_sum            'C13 H15 F3 N4'
_chemical_formula_weight         284.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3589(5)
_cell_length_b                   8.1467(4)
_cell_length_c                   15.8924(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.885(5)
_cell_angle_gamma                90.00
_cell_volume                     1448.80(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1125
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6480
_cell_measurement_theta_min      4.0930
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5607
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.47
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   56.00   87.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  -90.0000 21

#__ type_ start__ end____ width___ exp.time_
  2 omega   47.00   96.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00   71.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000   30.0000 18

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   30.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   23.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000   30.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0356551000
_diffrn_orient_matrix_UB_12      0.0556823000
_diffrn_orient_matrix_UB_13      -0.0277673000
_diffrn_orient_matrix_UB_21      0.0424639000
_diffrn_orient_matrix_UB_22      -0.0016906000
_diffrn_orient_matrix_UB_23      -0.0279142000
_diffrn_orient_matrix_UB_31      -0.0307499000
_diffrn_orient_matrix_UB_32      -0.0668987000
_diffrn_orient_matrix_UB_33      -0.0223964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1506
_reflns_number_total             2830
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0691P)²+0.3381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1959
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C3')
\\sim Ueq, Uanis(C1') \\sim Ueq, Uanis(C2') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F2'(0.3) F3'(0.3) C1'(0.4) H1'A(0.4) H1'B(0.4) H1'C(0.4) C2'(0.4)
 H2'A(0.4) H2'B(0.4) H2'C(0.4) C3'(0.4) H3'A(0.4) H3'B(0.4) H3'C(0.4) C9(0.6)
 H9A(0.6) H9B(0.6) H9C(0.6) F3(0.7) F2(0.7) C8(0.6) H8A(0.6) H8B(0.6) H8C(0.6)
 C10(0.6) H10A(0.6) H10B(0.6) H10C(0.6)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
4.c Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C2'(H2'A,H2'B,H2'C), C3'(H3'A,H3'B,H3'C), C9(H9A,H9B,
 H9C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F -0.0751(2) 0.4112(4) 0.12982(19) 0.1386(11) Uani 1 d A . . .
N1 N 0.3246(2) 0.5208(3) 0.12117(14) 0.0578(7) Uani 1 d . . . .
N2 N 0.4303(2) 0.4404(4) 0.13817(16) 0.0768(9) Uani 1 d . . . .
N3 N 0.4158(3) 0.3223(4) 0.18996(18) 0.0855(9) Uani 1 d . . . .
N4 N 0.3027(3) 0.3232(4) 0.20746(17) 0.0787(9) Uani 1 d . . . .
C1 C 0.2607(3) 0.8015(4) 0.08462(18) 0.0670(9) Uani 1 d . . . .
H1 H 0.2354 0.8119 0.1370 0.080 Uiso 1 calc . . R .
C2 C 0.2482(3) 0.9302(4) 0.02745(18) 0.0703(10) Uani 1 d . . . .
H2 H 0.2128 1.0270 0.0415 0.084 Uiso 1 calc . . R .
C3 C 0.2871(3) 0.9193(3) -0.05029(16) 0.0566(8) Uani 1 d B . . .
C4 C 0.3378(3) 0.7735(4) -0.06872(17) 0.0565(8) Uani 1 d . . . .
H4 H 0.3650 0.7631 -0.1204 0.068 Uiso 1 calc . . R .
C5 C 0.3500(3) 0.6420(4) -0.01325(16) 0.0563(8) Uani 1 d . . . .
H5 H 0.3841 0.5443 -0.0275 0.068 Uiso 1 calc . . R .
C6 C 0.3111(3) 0.6578(3) 0.06293(16) 0.0528(7) Uani 1 d . . . .
C7 C 0.2755(3) 1.0633(4) -0.11253(19) 0.0688(9) Uani 1 d . . . .
C11 C 0.2476(3) 0.4472(4) 0.16464(18) 0.0604(8) Uani 1 d . . . .
C12 C 0.1209(3) 0.4942(4) 0.1622(2) 0.0732(10) Uani 1 d A . . .
H12A H 0.1114 0.5334 0.2182 0.088 Uiso 1 calc . . R .
H12B H 0.1017 0.5844 0.1223 0.088 Uiso 1 calc . . R .
C13 C 0.0365(4) 0.3619(8) 0.1374(3) 0.1057(15) Uani 1 d . . . .
F2' F 0.0552(18) 0.233(2) 0.135(2) 0.169(11) Uani 0.30 d A 2 . .
F3' F 0.0484(19) 0.399(3) 0.0400(10) 0.189(9) Uani 0.30 d A 2 . .
C1' C 0.1945(17) 1.026(2) -0.1872(12) 0.143(9) Uani 0.40 d B 2 . U
H1'A H 0.2157 0.9226 -0.2095 0.214 Uiso 0.40 calc B 2 GR .
H1'B H 0.1972 1.1104 -0.2289 0.214 Uiso 0.40 calc B 2 GR .
H1'C H 0.1152 1.0190 -0.1742 0.214 Uiso 0.40 calc B 2 GR .
C2' C 0.4041(16) 1.077(2) -0.1420(12) 0.139(7) Uani 0.40 d B 2 . U
H2'A H 0.4652 1.0892 -0.0926 0.208 Uiso 0.40 calc B 2 GR .
H2'B H 0.4048 1.1705 -0.1787 0.208 Uiso 0.40 calc B 2 GR .
H2'C H 0.4188 0.9792 -0.1724 0.208 Uiso 0.40 calc B 2 GR .
C3' C 0.277(2) 1.2216(13) -0.0679(9) 0.126(5) Uani 0.40 d B 2 . U
H3'A H 0.2014 1.2381 -0.0495 0.189 Uiso 0.40 calc B 2 GR .
H3'B H 0.2901 1.3087 -0.1059 0.189 Uiso 0.40 calc B 2 GR .
H3'C H 0.3396 1.2215 -0.0191 0.189 Uiso 0.40 calc B 2 GR .
C9 C 0.2576(13) 1.0086(16) -0.2043(6) 0.126(5) Uani 0.60 d B 1 . U
H9A H 0.3260 0.9468 -0.2141 0.189 Uiso 0.60 calc B 1 GR .
H9B H 0.2480 1.1030 -0.2410 0.189 Uiso 0.60 calc B 1 GR .
H9C H 0.1875 0.9410 -0.2164 0.189 Uiso 0.60 calc B 1 GR .
F3 F 0.0496(6) 0.2493(9) 0.2059(5) 0.150(3) Uani 0.70 d A 1 . .
F2 F 0.0483(8) 0.2754(13) 0.0728(6) 0.159(5) Uani 0.70 d A 1 . .
C8 C 0.1635(11) 1.1682(14) -0.1070(7) 0.147(4) Uani 0.60 d B 1 . U
H8A H 0.0938 1.0995 -0.1163 0.221 Uiso 0.60 calc B 1 GR .
H8B H 0.1556 1.2525 -0.1498 0.221 Uiso 0.60 calc B 1 GR .
H8C H 0.1717 1.2176 -0.0515 0.221 Uiso 0.60 calc B 1 GR .
C10 C 0.3817(13) 1.1663(15) -0.0966(9) 0.154(6) Uani 0.60 d B 1 . U
H10A H 0.3986 1.1953 -0.0372 0.231 Uiso 0.60 calc B 1 GR .
H10B H 0.3682 1.2642 -0.1305 0.231 Uiso 0.60 calc B 1 GR .
H10C H 0.4483 1.1073 -0.1116 0.231 Uiso 0.60 calc B 1 GR .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.315(5) . ?
N1 N2 1.353(3) . ?
N1 C6 1.441(3) . ?
N1 C11 1.345(4) . ?
N2 N3 1.295(3) . ?
N3 N4 1.361(4) . ?
N4 C11 1.314(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(4) . ?
C1 C6 1.373(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 C4 1.374(4) . ?
C3 C7 1.525(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(4) . ?
C7 C1' 1.404(15) . ?
C7 C2' 1.613(16) . ?
C7 C3' 1.471(12) . ?
C7 C9 1.505(10) . ?
C7 C8 1.547(9) . ?
C7 C10 1.455(11) . ?
C11 C12 1.484(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.451(6) . ?
C13 F2' 1.072(16) . ?
C13 F3' 1.604(19) . ?
C13 F3 1.412(9) . ?
C13 F2 1.272(9) . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C2' H2'A 0.9600 . ?
C2' H2'B 0.9600 . ?
C2' H2'C 0.9600 . ?
C3' H3'A 0.9600 . ?
C3' H3'B 0.9600 . ?
C3' H3'C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N2 N1 C6 119.7(2) . . ?
C11 N1 N2 108.3(2) . . ?
C11 N1 C6 131.9(3) . . ?
N3 N2 N1 106.3(3) . . ?
N2 N3 N4 110.7(3) . . ?
C11 N4 N3 106.3(3) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.9(3) . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C7 121.6(3) . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C7 121.3(3) . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.3(3) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 N1 120.1(2) . . ?
C5 C6 N1 118.8(3) . . ?
C5 C6 C1 121.0(3) . . ?
C3 C7 C2' 105.1(6) . . ?
C3 C7 C8 111.6(4) . . ?
C1' C7 C3 110.6(8) . . ?
C1' C7 C2' 105.3(11) . . ?
C1' C7 C3' 123.3(12) . . ?
C1' C7 C9 32.6(10) . . ?
C1' C7 C8 75.0(10) . . ?
C1' C7 C10 132.5(9) . . ?
C3' C7 C3 111.6(5) . . ?
C3' C7 C2' 98.4(10) . . ?
C3' C7 C9 135.7(8) . . ?
C3' C7 C8 55.1(8) . . ?
C9 C7 C3 112.5(6) . . ?
C9 C7 C2' 73.6(9) . . ?
C9 C7 C8 104.1(7) . . ?
C8 C7 C2' 140.6(7) . . ?
C10 C7 C3 110.7(5) . . ?
C10 C7 C2' 41.0(7) . . ?
C10 C7 C3' 58.1(8) . . ?
C10 C7 C9 108.0(8) . . ?
C10 C7 C8 109.7(7) . . ?
N1 C11 C12 125.8(3) . . ?
N4 C11 N1 108.4(3) . . ?
N4 C11 C12 125.8(3) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.1(3) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
F1 C13 C12 112.3(5) . . ?
F1 C13 F3' 95.4(9) . . ?
F1 C13 F3 104.0(5) . . ?
C12 C13 F3' 87.8(9) . . ?
F2' C13 F1 119.2(11) . . ?
F2' C13 C12 127.6(12) . . ?
F2' C13 F3' 95.9(16) . . ?
F2' C13 F3 52.6(16) . . ?
F2' C13 F2 52.0(14) . . ?
F3 C13 C12 107.2(5) . . ?
F3 C13 F3' 148.2(10) . . ?
F2 C13 F1 109.2(5) . . ?
F2 C13 C12 118.3(7) . . ?
F2 C13 F3' 44.5(7) . . ?
F2 C13 F3 104.5(8) . . ?
C7 C1' H1'A 109.5 . . ?
C7 C1' H1'B 109.5 . . ?
C7 C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C7 C2' H2'A 109.5 . . ?
C7 C2' H2'B 109.5 . . ?
C7 C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C7 C3' H3'A 109.5 . . ?
C7 C3' H3'B 109.5 . . ?
C7 C3' H3'C 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?

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
N1 N2 N3 N4 0.0(4) . . . . ?
N1 C11 C12 C13 123.7(4) . . . . ?
N2 N1 C6 C1 -132.5(3) . . . . ?
N2 N1 C6 C5 47.0(4) . . . . ?
N2 N1 C11 N4 -0.4(3) . . . . ?
N2 N1 C11 C12 -178.4(3) . . . . ?
N2 N3 N4 C11 -0.2(4) . . . . ?
N3 N4 C11 N1 0.4(3) . . . . ?
N3 N4 C11 C12 178.3(3) . . . . ?
N4 C11 C12 C13 -53.9(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C7 -178.7(3) . . . . ?
C2 C1 C6 N1 -179.6(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C7 C1' -113.7(11) . . . . ?
C2 C3 C7 C2' 133.1(9) . . . . ?
C2 C3 C7 C3' 27.5(12) . . . . ?
C2 C3 C7 C9 -148.8(7) . . . . ?
C2 C3 C7 C8 -32.2(7) . . . . ?
C2 C3 C7 C10 90.3(9) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C3 C7 C1' 67.0(11) . . . . ?
C4 C3 C7 C2' -46.2(9) . . . . ?
C4 C3 C7 C3' -151.8(11) . . . . ?
C4 C3 C7 C9 32.0(7) . . . . ?
C4 C3 C7 C8 148.5(7) . . . . ?
C4 C3 C7 C10 -89.0(9) . . . . ?
C4 C5 C6 N1 -179.5(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C6 N1 N2 N3 -178.4(2) . . . . ?
C6 N1 C11 N4 178.0(3) . . . . ?
C6 N1 C11 C12 0.1(5) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
C7 C3 C4 C5 179.6(3) . . . . ?
C11 N1 N2 N3 0.3(3) . . . . ?
C11 N1 C6 C1 49.2(4) . . . . ?
C11 N1 C6 C5 -131.2(3) . . . . ?
C11 C12 C13 F1 -175.3(4) . . . . ?
C11 C12 C13 F2' 15(2) . . . . ?
C11 C12 C13 F3' -80.4(9) . . . . ?
C11 C12 C13 F3 71.1(6) . . . . ?
C11 C12 C13 F2 -46.6(9) . . . . ?

_olex2_date_sample_data_collection 2015-03-13
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_heyt0504
_database_code_depnum_ccdc_archive 'CCDC 1407787'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H22 F3 N O2'
_chemical_formula_sum            'C24 H22 F3 N O2'
_chemical_formula_weight         413.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.4249(17)
_cell_length_b                   6.2204(3)
_cell_length_c                   20.9937(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.885(4)
_cell_angle_gamma                90.00
_cell_volume                     4333.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1352
_cell_measurement_temperature    293.6(2)
_cell_measurement_theta_max      21.7380
_cell_measurement_theta_min      3.8190
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8148
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000   90.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0021901000
_diffrn_orient_matrix_UB_12      -0.0164466000
_diffrn_orient_matrix_UB_13      -0.0328351000
_diffrn_orient_matrix_UB_21      0.0160779000
_diffrn_orient_matrix_UB_22      -0.0725530000
_diffrn_orient_matrix_UB_23      0.0088462000
_diffrn_orient_matrix_UB_31      -0.0139197000
_diffrn_orient_matrix_UB_32      -0.0863998000
_diffrn_orient_matrix_UB_33      -0.0012025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2053
_reflns_number_total             4254
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.9196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1951
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F2') \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1') \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F1'(0.5) F2'(0.5) F3'(0.5) C13'(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
 C14'(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C15'(0.5) H15A(0.5) H15B(0.5)
 H15C(0.5) C13(0.5) H2A(0.5) H2B(0.5) H2C(0.5) F2(0.5) C15(0.5) H3A(0.5)
 H3B(0.5) H3C(0.5) F1(0.5) F3(0.5) C14(0.5) H1B(0.5) H1A(0.5) H1C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
4.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C13'(H13A,H13B,H13C), C14'(H14A,H14B,H14C), C15'(H15A,
 H15B,H15C), C13(H2A,H2B,H2C), C15(H3A,H3B,H3C), C14(H1B,H1A,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.21528(7) 0.0609(3) 0.49731(11) 0.0781(7) Uani 1 d . . . .
O2 O 0.23570(6) 0.0477(3) 0.39990(10) 0.0644(6) Uani 1 d . . . .
N1 N 0.16500(7) 0.3962(4) 0.45731(11) 0.0533(6) Uani 1 d . . . .
C1 C 0.14058(8) 0.5591(4) 0.43659(14) 0.0523(7) Uani 1 d . . . .
C2 C 0.14000(8) 0.6452(4) 0.37475(14) 0.0537(7) Uani 1 d A . . .
C3 C 0.16724(8) 0.5674(4) 0.33413(13) 0.0519(7) Uani 1 d . . . .
C4 C 0.19241(8) 0.4000(4) 0.35727(13) 0.0538(7) Uani 1 d . . . .
H4 H 0.2109 0.3433 0.3321 0.065 Uiso 1 calc . . R .
C5 C 0.18986(8) 0.3179(4) 0.41784(14) 0.0511(7) Uani 1 d . . . .
C6 C 0.11382(8) 0.6304(5) 0.48463(13) 0.0539(7) Uani 1 d . . . .
C7 C 0.11729(9) 0.8265(5) 0.51446(18) 0.0750(10) Uani 1 d . . . .
H7 H 0.1365 0.9240 0.5036 0.090 Uiso 1 calc . . R .
C8 C 0.09282(10) 0.8818(6) 0.56035(17) 0.0780(10) Uani 1 d . . . .
H8 H 0.0964 1.0148 0.5804 0.094 Uiso 1 calc . . R .
C9 C 0.06323(9) 0.7463(5) 0.57739(15) 0.0630(8) Uani 1 d B . . .
C10 C 0.06039(11) 0.5508(5) 0.54721(19) 0.0832(11) Uani 1 d . . . .
H10 H 0.0409 0.4542 0.5573 0.100 Uiso 1 calc . . R .
C11 C 0.08534(10) 0.4914(5) 0.50244(18) 0.0792(11) Uani 1 d . . . .
H11 H 0.0828 0.3552 0.4841 0.095 Uiso 1 calc . . R .
C12 C 0.03552(11) 0.8076(6) 0.6274(2) 0.0841(11) Uani 1 d . . . .
C16 C 0.10886(12) 0.8109(7) 0.35026(19) 0.0773(10) Uani 1 d . . . .
C17 C 0.17072(9) 0.6466(5) 0.26803(14) 0.0581(8) Uani 1 d . . . .
C18 C 0.18935(12) 0.8378(6) 0.25743(18) 0.0894(12) Uani 1 d . . . .
H18 H 0.1994 0.9238 0.2919 0.107 Uiso 1 calc . . R .
C19 C 0.19324(15) 0.9026(7) 0.1954(2) 0.1138(15) Uani 1 d . . . .
H19 H 0.2063 1.0314 0.1887 0.137 Uiso 1 calc . . R .
C20 C 0.17842(15) 0.7821(9) 0.1443(2) 0.1083(16) Uani 1 d . . . .
H20 H 0.1805 0.8283 0.1027 0.130 Uiso 1 calc . . R .
C21 C 0.16064(13) 0.5948(9) 0.1550(2) 0.1122(15) Uani 1 d . . . .
H21 H 0.1505 0.5105 0.1202 0.135 Uiso 1 calc . . R .
C22 C 0.15697(11) 0.5239(6) 0.21605(17) 0.0919(12) Uani 1 d . . . .
H22 H 0.1450 0.3914 0.2220 0.110 Uiso 1 calc . . R .
C23 C 0.21452(8) 0.1301(5) 0.44386(15) 0.0542(7) Uani 1 d . . . .
C24 C 0.26045(10) -0.1366(5) 0.41949(17) 0.0767(10) Uani 1 d . . . .
H24A H 0.2718 -0.1936 0.3831 0.115 Uiso 1 calc . . GR .
H24B H 0.2443 -0.2447 0.4367 0.115 Uiso 1 calc . . GR .
H24C H 0.2818 -0.0939 0.4517 0.115 Uiso 1 calc . . GR .
F1' F 0.0779(4) 0.820(2) 0.3803(5) 0.148(6) Uani 0.50 d A 2 . U
F2' F 0.1226(4) 0.993(2) 0.3416(6) 0.132(4) Uani 0.50 d A 2 . U
F3' F 0.0924(3) 0.7554(18) 0.2905(6) 0.109(4) Uani 0.50 d A 2 . U
C13' C 0.0564(4) 0.933(4) 0.6786(7) 0.152(7) Uani 0.50 d B 2 . .
H13A H 0.0805 0.8589 0.6958 0.229 Uiso 0.50 calc B 2 GR .
H13B H 0.0393 0.9520 0.7117 0.229 Uiso 0.50 calc B 2 GR .
H13C H 0.0632 1.0704 0.6624 0.229 Uiso 0.50 calc B 2 GR .
C14' C 0.0016(4) 0.946(3) 0.5880(6) 0.136(4) Uani 0.50 d B 2 . .
H14A H 0.0133 1.0741 0.5726 0.204 Uiso 0.50 calc B 2 GR .
H14B H -0.0184 0.9849 0.6152 0.204 Uiso 0.50 calc B 2 GR .
H14C H -0.0108 0.8639 0.5522 0.204 Uiso 0.50 calc B 2 GR .
C15' C 0.0148(7) 0.611(3) 0.6518(9) 0.152(6) Uani 0.50 d B 2 . .
H15A H 0.0014 0.5328 0.6161 0.228 Uiso 0.50 calc B 2 GR .
H15B H -0.0046 0.6570 0.6792 0.228 Uiso 0.50 calc B 2 GR .
H15C H 0.0345 0.5210 0.6756 0.228 Uiso 0.50 calc B 2 GR .
C13 C 0.0330(6) 1.0447(19) 0.6401(10) 0.154(5) Uani 0.50 d B 1 . .
H2A H 0.0592 1.0975 0.6567 0.231 Uiso 0.50 calc B 1 GR .
H2B H 0.0145 1.0699 0.6709 0.231 Uiso 0.50 calc B 1 GR .
H2C H 0.0238 1.1182 0.6008 0.231 Uiso 0.50 calc B 1 GR .
F2 F 0.1170(5) 1.005(2) 0.3792(6) 0.140(5) Uani 0.50 d A 1 . U
C15 C -0.0058(4) 0.725(4) 0.6141(10) 0.157(7) Uani 0.50 d B 1 . .
H3A H -0.0177 0.7759 0.5730 0.235 Uiso 0.50 calc B 1 GR .
H3B H -0.0215 0.7748 0.6467 0.235 Uiso 0.50 calc B 1 GR .
H3C H -0.0053 0.5708 0.6141 0.235 Uiso 0.50 calc B 1 GR .
F1 F 0.0734(3) 0.758(2) 0.3650(7) 0.116(4) Uani 0.50 d A 1 . U
F3 F 0.1039(4) 0.839(3) 0.2895(6) 0.163(6) Uani 0.50 d A 1 . U
C14 C 0.0539(5) 0.704(4) 0.6939(6) 0.167(7) Uani 0.50 d B 1 . .
H1B H 0.0360 0.7302 0.7256 0.251 Uiso 0.50 calc B 1 GR .
H1A H 0.0797 0.7680 0.7076 0.251 Uiso 0.50 calc B 1 GR .
H1C H 0.0571 0.5521 0.6887 0.251 Uiso 0.50 calc B 1 GR .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.199(3) . ?
O2 C23 1.331(3) . ?
O2 C24 1.444(3) . ?
N1 C1 1.340(3) . ?
N1 C5 1.334(3) . ?
C1 C2 1.403(4) . ?
C1 C6 1.493(4) . ?
C2 C3 1.406(4) . ?
C2 C16 1.511(4) . ?
C3 C4 1.389(4) . ?
C3 C17 1.490(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C23 1.495(4) . ?
C6 C7 1.370(4) . ?
C6 C11 1.371(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
C9 C10 1.370(4) . ?
C9 C12 1.529(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13' 1.437(11) . ?
C12 C14' 1.577(11) . ?
C12 C15' 1.522(14) . ?
C12 C13 1.503(11) . ?
C12 C15 1.469(13) . ?
C12 C14 1.594(12) . ?
C16 F1' 1.276(11) . ?
C16 F2' 1.244(14) . ?
C16 F3' 1.354(12) . ?
C16 F2 1.364(14) . ?
C16 F1 1.304(12) . ?
C16 F3 1.278(12) . ?
C17 C18 1.373(4) . ?
C17 C22 1.366(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.353(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.339(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(5) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C13' H13A 0.9600 . ?
C13' H13B 0.9600 . ?
C13' H13C 0.9600 . ?
C14' H14A 0.9600 . ?
C14' H14B 0.9600 . ?
C14' H14C 0.9600 . ?
C15' H15A 0.9600 . ?
C15' H15B 0.9600 . ?
C15' H15C 0.9600 . ?
C13 H2A 0.9600 . ?
C13 H2B 0.9600 . ?
C13 H2C 0.9600 . ?
C15 H3A 0.9600 . ?
C15 H3B 0.9600 . ?
C15 H3C 0.9600 . ?
C14 H1B 0.9600 . ?
C14 H1A 0.9600 . ?
C14 H1C 0.9600 . ?

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
C23 O2 C24 116.3(2) . . ?
C5 N1 C1 118.3(2) . . ?
N1 C1 C2 122.0(3) . . ?
N1 C1 C6 113.3(2) . . ?
C2 C1 C6 124.6(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 C16 120.6(3) . . ?
C3 C2 C16 119.9(3) . . ?
C2 C3 C17 125.4(3) . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C17 117.5(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 123.2(3) . . ?
N1 C5 C23 114.6(3) . . ?
C4 C5 C23 122.2(3) . . ?
C7 C6 C1 123.3(3) . . ?
C7 C6 C11 117.4(3) . . ?
C11 C6 C1 119.2(3) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C12 122.6(3) . . ?
C10 C9 C8 115.8(3) . . ?
C10 C9 C12 121.7(3) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(3) . . ?
C11 C10 H10 118.7 . . ?
C6 C11 C10 120.9(3) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C9 C12 C14' 103.5(5) . . ?
C9 C12 C14 107.4(5) . . ?
C13' C12 C9 111.6(5) . . ?
C13' C12 C14' 110.5(9) . . ?
C13' C12 C15' 112.4(10) . . ?
C13' C12 C13 50.8(7) . . ?
C13' C12 C15 133.7(8) . . ?
C13' C12 C14 57.4(8) . . ?
C14' C12 C14 149.1(6) . . ?
C15' C12 C9 111.7(6) . . ?
C15' C12 C14' 106.7(9) . . ?
C15' C12 C14 61.6(8) . . ?
C13 C12 C9 114.7(5) . . ?
C13 C12 C14' 60.4(7) . . ?
C13 C12 C15' 133.6(7) . . ?
C13 C12 C14 105.3(9) . . ?
C15 C12 C9 114.6(7) . . ?
C15 C12 C14' 59.4(8) . . ?
C15 C12 C15' 47.8(8) . . ?
C15 C12 C13 107.8(9) . . ?
C15 C12 C14 106.3(10) . . ?
F1' C16 C2 115.3(6) . . ?
F1' C16 F3' 101.8(9) . . ?
F1' C16 F2 82.6(9) . . ?
F1' C16 F1 22.9(10) . . ?
F1' C16 F3 118.2(8) . . ?
F2' C16 C2 114.8(7) . . ?
F2' C16 F1' 111.7(10) . . ?
F2' C16 F3' 102.3(8) . . ?
F2' C16 F2 37.1(9) . . ?
F2' C16 F1 128.9(9) . . ?
F2' C16 F3 74.7(8) . . ?
F3' C16 C2 109.2(6) . . ?
F3' C16 F2 132.5(8) . . ?
F2 C16 C2 111.2(7) . . ?
F1 C16 C2 110.8(7) . . ?
F1 C16 F3' 82.8(8) . . ?
F1 C16 F2 104.9(9) . . ?
F3 C16 C2 115.7(6) . . ?
F3 C16 F3' 28.3(10) . . ?
F3 C16 F2 108.6(10) . . ?
F3 C16 F1 105.0(9) . . ?
C18 C17 C3 121.6(3) . . ?
C22 C17 C3 120.2(3) . . ?
C22 C17 C18 118.1(3) . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.5(4) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.1 . . ?
C20 C21 C22 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C17 C22 C21 120.4(4) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
O1 C23 O2 123.8(3) . . ?
O1 C23 C5 124.8(3) . . ?
O2 C23 C5 111.3(3) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C12 C13' H13A 109.5 . . ?
C12 C13' H13B 109.5 . . ?
C12 C13' H13C 109.5 . . ?
H13A C13' H13B 109.5 . . ?
H13A C13' H13C 109.5 . . ?
H13B C13' H13C 109.5 . . ?
C12 C14' H14A 109.5 . . ?
C12 C14' H14B 109.5 . . ?
C12 C14' H14C 109.5 . . ?
H14A C14' H14B 109.5 . . ?
H14A C14' H14C 109.5 . . ?
H14B C14' H14C 109.5 . . ?
C12 C15' H15A 109.5 . . ?
C12 C15' H15B 109.5 . . ?
C12 C15' H15C 109.5 . . ?
H15A C15' H15B 109.5 . . ?
H15A C15' H15C 109.5 . . ?
H15B C15' H15C 109.5 . . ?
C12 C13 H2A 109.5 . . ?
C12 C13 H2B 109.5 . . ?
C12 C13 H2C 109.5 . . ?
C12 C15 H3A 109.5 . . ?
C12 C15 H3B 109.5 . . ?
C12 C15 H3C 109.5 . . ?
C12 C14 H1B 109.5 . . ?
C12 C14 H1A 109.5 . . ?
C12 C14 H1C 109.5 . . ?

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
N1 C1 C2 C3 -3.5(4) . . . . ?
N1 C1 C2 C16 172.9(3) . . . . ?
N1 C1 C6 C7 112.4(3) . . . . ?
N1 C1 C6 C11 -64.6(4) . . . . ?
N1 C5 C23 O1 -5.8(4) . . . . ?
N1 C5 C23 O2 174.0(2) . . . . ?
C1 N1 C5 C4 1.7(4) . . . . ?
C1 N1 C5 C23 -177.3(2) . . . . ?
C1 C2 C3 C4 2.8(4) . . . . ?
C1 C2 C3 C17 -178.6(3) . . . . ?
C1 C2 C16 F1' -18.9(10) . . . . ?
C1 C2 C16 F2' 113.1(8) . . . . ?
C1 C2 C16 F3' -132.8(6) . . . . ?
C1 C2 C16 F2 72.8(9) . . . . ?
C1 C2 C16 F1 -43.4(8) . . . . ?
C1 C2 C16 F3 -162.7(9) . . . . ?
C1 C6 C7 C8 -177.5(3) . . . . ?
C1 C6 C11 C10 179.3(3) . . . . ?
C2 C1 C6 C7 -69.8(4) . . . . ?
C2 C1 C6 C11 113.2(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C17 C18 76.3(4) . . . . ?
C2 C3 C17 C22 -106.9(4) . . . . ?
C3 C2 C16 F1' 157.5(9) . . . . ?
C3 C2 C16 F2' -70.5(8) . . . . ?
C3 C2 C16 F3' 43.6(7) . . . . ?
C3 C2 C16 F2 -110.7(8) . . . . ?
C3 C2 C16 F1 133.0(7) . . . . ?
C3 C2 C16 F3 13.7(11) . . . . ?
C3 C4 C5 N1 -2.3(4) . . . . ?
C3 C4 C5 C23 176.6(3) . . . . ?
C3 C17 C18 C19 177.8(3) . . . . ?
C3 C17 C22 C21 -179.0(3) . . . . ?
C4 C3 C17 C18 -105.1(4) . . . . ?
C4 C3 C17 C22 71.7(4) . . . . ?
C4 C5 C23 O1 175.3(3) . . . . ?
C4 C5 C23 O2 -4.9(4) . . . . ?
C5 N1 C1 C2 1.3(4) . . . . ?
C5 N1 C1 C6 179.2(2) . . . . ?
C6 C1 C2 C3 178.8(3) . . . . ?
C6 C1 C2 C16 -4.8(5) . . . . ?
C6 C7 C8 C9 -1.6(6) . . . . ?
C7 C6 C11 C10 2.1(5) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C7 C8 C9 C12 -179.0(4) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C8 C9 C12 C13' -36.0(12) . . . . ?
C8 C9 C12 C14' 82.8(8) . . . . ?
C8 C9 C12 C15' -162.8(11) . . . . ?
C8 C9 C12 C13 19.5(11) . . . . ?
C8 C9 C12 C15 145.0(12) . . . . ?
C8 C9 C12 C14 -97.1(11) . . . . ?
C9 C10 C11 C6 -1.9(6) . . . . ?
C10 C9 C12 C13' 143.2(12) . . . . ?
C10 C9 C12 C14' -98.0(8) . . . . ?
C10 C9 C12 C15' 16.4(12) . . . . ?
C10 C9 C12 C13 -161.3(11) . . . . ?
C10 C9 C12 C15 -35.7(13) . . . . ?
C10 C9 C12 C14 82.1(12) . . . . ?
C11 C6 C7 C8 -0.4(5) . . . . ?
C12 C9 C10 C11 -179.4(4) . . . . ?
C16 C2 C3 C4 -173.7(3) . . . . ?
C16 C2 C3 C17 5.0(5) . . . . ?
C17 C3 C4 C5 -178.8(3) . . . . ?
C17 C18 C19 C20 1.0(7) . . . . ?
C18 C17 C22 C21 -2.1(5) . . . . ?
C18 C19 C20 C21 -1.6(7) . . . . ?
C19 C20 C21 C22 0.4(7) . . . . ?
C20 C21 C22 C17 1.6(7) . . . . ?
C22 C17 C18 C19 0.9(5) . . . . ?
C24 O2 C23 O1 0.4(4) . . . . ?
C24 O2 C23 C5 -179.4(2) . . . . ?

_olex2_date_sample_data_collection 2015-05-04
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_heyt0428
_database_code_depnum_ccdc_archive 'CCDC 1407788'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_audit_creation_date             2015-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H19 F3 N2'
_chemical_formula_sum            'C21 H19 F3 N2'
_chemical_formula_weight         356.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

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

_cell_length_a                   9.987(3)
_cell_length_b                   10.061(3)
_cell_length_c                   10.1680(16)
_cell_angle_alpha                71.21(2)
_cell_angle_beta                 75.39(2)
_cell_angle_gamma                79.84(2)
_cell_volume                     930.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1037
_cell_measurement_temperature    295.42(10)
_cell_measurement_theta_max      22.0230
_cell_measurement_theta_min      4.1560
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_av_unetI/netI     0.1787
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6242
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   43.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666   57.0000  120.0000 20

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   90.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666   57.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   92.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666   38.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   22.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000 -120.0000 17

#__ type_ start__ end____ width___ exp.time_
  5 omega  -36.00   42.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666  -57.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   91.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       21.3666  178.0000  -90.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0696655000
_diffrn_orient_matrix_UB_12      -0.0235870000
_diffrn_orient_matrix_UB_13      0.0075166000
_diffrn_orient_matrix_UB_21      0.0147981000
_diffrn_orient_matrix_UB_22      0.0710605000
_diffrn_orient_matrix_UB_23      -0.0197236000
_diffrn_orient_matrix_UB_31      -0.0193270000
_diffrn_orient_matrix_UB_32      -0.0009125000
_diffrn_orient_matrix_UB_33      0.0723467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1222
_reflns_number_total             3647
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.24(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1818
_refine_ls_R_factor_gt           0.0880
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1454P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.3307
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.3575(3) 0.0206(4) 0.4873(4) 0.1245(16) Uani 1 d . . .
F2 F 0.1953(4) -0.1132(4) 0.5792(3) 0.1044(12) Uani 1 d . . .
F3 F 0.2483(3) -0.0247(3) 0.3565(3) 0.0894(11) Uani 1 d . . .
N1 N 0.0028(4) 0.3474(4) 0.4014(4) 0.0680(11) Uani 1 d . . .
N2 N 0.0654(4) 0.1197(4) 0.6228(4) 0.0617(11) Uani 1 d . . .
C1 C -0.1528(5) 0.3343(5) 0.8376(5) 0.0696(14) Uani 1 d . . .
H1 H -0.1391 0.4228 0.7728 0.083 Uiso 1 calc . . R
C2 C -0.2205(5) 0.3238(6) 0.9741(6) 0.0747(14) Uani 1 d . . .
H2 H -0.2518 0.4054 1.0016 0.090 Uiso 1 calc . . R
C3 C -0.2430(5) 0.1970(7) 1.0701(5) 0.0815(17) Uani 1 d . . .
H3 H -0.2910 0.1915 1.1625 0.098 Uiso 1 calc . . R
C4 C -0.1939(6) 0.0737(7) 1.0300(5) 0.0916(18) Uani 1 d . . .
H4 H -0.2055 -0.0142 1.0967 0.110 Uiso 1 calc . . R
C5 C -0.1303(5) 0.0826(5) 0.8958(5) 0.0736(14) Uani 1 d . . .
H5 H -0.1027 0.0003 0.8688 0.088 Uiso 1 calc . . R
C6 C -0.1039(5) 0.2132(5) 0.7941(5) 0.0604(12) Uani 1 d . . .
C7 C -0.0335(5) 0.2235(5) 0.6482(5) 0.0600(12) Uani 1 d . . .
C8 C -0.0599(5) 0.3345(5) 0.5320(5) 0.0690(14) Uani 1 d . . .
H8 H -0.1286 0.4059 0.5494 0.083 Uiso 1 calc . . R
C10 C 0.1081(5) 0.2466(5) 0.3737(4) 0.0572(12) Uani 1 d . . .
C11 C 0.1303(5) 0.1307(5) 0.4894(5) 0.0632(13) Uani 1 d . . .
C13 C 0.2340(5) 0.0029(6) 0.4762(5) 0.0694(14) Uani 1 d . . .
C14 C 0.1780(5) 0.2686(5) 0.2248(5) 0.0621(12) Uani 1 d . . .
C15 C 0.1014(5) 0.3048(5) 0.1201(5) 0.0658(13) Uani 1 d . . .
H15 H 0.0048 0.3125 0.1463 0.079 Uiso 1 calc . . R
C16 C 0.1635(5) 0.3298(5) -0.0215(5) 0.0699(14) Uani 1 d . . .
H16 H 0.1077 0.3530 -0.0880 0.084 Uiso 1 calc . . R
C17 C 0.3054(5) 0.3215(5) -0.0675(5) 0.0666(13) Uani 1 d . . .
C18 C 0.3824(6) 0.2880(6) 0.0367(5) 0.0822(16) Uani 1 d . . .
H18 H 0.4789 0.2834 0.0095 0.099 Uiso 1 calc . . R
C19 C 0.3224(5) 0.2614(6) 0.1782(5) 0.0754(15) Uani 1 d . . .
H19 H 0.3786 0.2381 0.2443 0.090 Uiso 1 calc . . R
C20 C 0.3759(5) 0.3543(6) -0.2234(5) 0.0767(15) Uani 1 d . . .
C21 C 0.2809(7) 0.3468(9) -0.3141(6) 0.125(3) Uani 1 d . . .
H21A H 0.2276 0.2678 -0.2658 0.188 Uiso 1 calc . . GR
H21B H 0.3354 0.3356 -0.4030 0.188 Uiso 1 calc . . GR
H21C H 0.2190 0.4323 -0.3314 0.188 Uiso 1 calc . . GR
C22 C 0.4983(7) 0.2443(11) -0.2463(7) 0.160(4) Uani 1 d . . .
H22A H 0.5787 0.2684 -0.2269 0.239 Uiso 1 calc . . GR
H22B H 0.5177 0.2418 -0.3429 0.239 Uiso 1 calc . . GR
H22C H 0.4757 0.1532 -0.1834 0.239 Uiso 1 calc . . GR
C23 C 0.4278(14) 0.4947(10) -0.2719(8) 0.202(6) Uani 1 d . . .
H23A H 0.3504 0.5664 -0.2728 0.304 Uiso 1 calc . . GR
H23B H 0.4844 0.5093 -0.3660 0.304 Uiso 1 calc . . GR
H23C H 0.4823 0.4993 -0.2084 0.304 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.315(5) . ?
F2 C13 1.333(6) . ?
F3 C13 1.301(5) . ?
N1 C8 1.293(5) . ?
N1 C10 1.368(6) . ?
N2 C7 1.346(5) . ?
N2 C11 1.326(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(6) . ?
C1 C6 1.395(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.349(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.333(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(7) . ?
C6 C7 1.451(6) . ?
C7 C8 1.384(6) . ?
C8 H8 0.9300 . ?
C10 C11 1.395(6) . ?
C10 C14 1.461(6) . ?
C11 C13 1.522(6) . ?
C14 C15 1.383(6) . ?
C14 C19 1.396(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(7) . ?
C17 C18 1.384(6) . ?
C17 C20 1.517(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.506(7) . ?
C20 C22 1.522(8) . ?
C20 C23 1.479(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C8 N1 C10 118.2(4) . . ?
C11 N2 C7 118.1(4) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(5) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(5) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.2(4) . . ?
C1 C6 C7 120.8(4) . . ?
C5 C6 C7 121.9(4) . . ?
N2 C7 C6 118.5(4) . . ?
N2 C7 C8 117.2(4) . . ?
C8 C7 C6 124.3(4) . . ?
N1 C8 C7 125.6(4) . . ?
N1 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
N1 C10 C11 116.3(4) . . ?
N1 C10 C14 116.0(4) . . ?
C11 C10 C14 127.6(4) . . ?
N2 C11 C10 124.3(4) . . ?
N2 C11 C13 112.3(4) . . ?
C10 C11 C13 123.4(4) . . ?
F1 C13 F2 106.6(4) . . ?
F1 C13 C11 111.1(4) . . ?
F2 C13 C11 111.3(4) . . ?
F3 C13 F1 107.8(4) . . ?
F3 C13 F2 106.6(4) . . ?
F3 C13 C11 113.1(4) . . ?
C15 C14 C10 120.5(4) . . ?
C15 C14 C19 116.1(4) . . ?
C19 C14 C10 123.4(4) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 C14 122.1(4) . . ?
C16 C15 H15 118.9 . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.9(4) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 116.2(4) . . ?
C16 C17 C20 122.8(4) . . ?
C18 C17 C20 121.0(4) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 C17 122.7(5) . . ?
C19 C18 H18 118.6 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C17 C20 C22 110.5(5) . . ?
C21 C20 C17 112.1(4) . . ?
C21 C20 C22 104.8(5) . . ?
C23 C20 C17 109.5(4) . . ?
C23 C20 C21 111.0(7) . . ?
C23 C20 C22 108.8(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
N1 C10 C11 N2 -6.4(6) . . . . ?
N1 C10 C11 C13 174.5(4) . . . . ?
N1 C10 C14 C15 -46.8(5) . . . . ?
N1 C10 C14 C19 130.2(5) . . . . ?
N2 C7 C8 N1 -0.4(7) . . . . ?
N2 C11 C13 F1 -89.8(5) . . . . ?
N2 C11 C13 F2 28.8(5) . . . . ?
N2 C11 C13 F3 148.9(4) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C1 C6 C7 N2 149.0(4) . . . . ?
C1 C6 C7 C8 -30.1(6) . . . . ?
C2 C1 C6 C5 1.3(6) . . . . ?
C2 C1 C6 C7 179.0(4) . . . . ?
C2 C3 C4 C5 -2.8(8) . . . . ?
C3 C4 C5 C6 3.7(8) . . . . ?
C4 C5 C6 C1 -3.0(7) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C5 C6 C7 N2 -33.5(6) . . . . ?
C5 C6 C7 C8 147.4(5) . . . . ?
C6 C1 C2 C3 -0.5(7) . . . . ?
C6 C7 C8 N1 178.7(4) . . . . ?
C7 N2 C11 C10 3.6(6) . . . . ?
C7 N2 C11 C13 -177.2(4) . . . . ?
C8 N1 C10 C11 5.6(6) . . . . ?
C8 N1 C10 C14 -178.3(4) . . . . ?
C10 N1 C8 C7 -2.6(7) . . . . ?
C10 C11 C13 F1 89.4(5) . . . . ?
C10 C11 C13 F2 -151.9(4) . . . . ?
C10 C11 C13 F3 -31.9(6) . . . . ?
C10 C14 C15 C16 178.3(4) . . . . ?
C10 C14 C19 C18 -177.6(5) . . . . ?
C11 N2 C7 C6 -179.2(3) . . . . ?
C11 N2 C7 C8 -0.1(6) . . . . ?
C11 C10 C14 C15 128.8(5) . . . . ?
C11 C10 C14 C19 -54.2(6) . . . . ?
C14 C10 C11 N2 178.0(4) . . . . ?
C14 C10 C11 C13 -1.1(6) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C15 C14 C19 C18 -0.4(7) . . . . ?
C15 C16 C17 C18 -0.7(7) . . . . ?
C15 C16 C17 C20 -177.5(4) . . . . ?
C16 C17 C18 C19 1.4(8) . . . . ?
C16 C17 C20 C21 -19.6(7) . . . . ?
C16 C17 C20 C22 -136.2(6) . . . . ?
C16 C17 C20 C23 104.0(8) . . . . ?
C17 C18 C19 C14 -0.8(8) . . . . ?
C18 C17 C20 C21 163.6(5) . . . . ?
C18 C17 C20 C22 47.1(7) . . . . ?
C18 C17 C20 C23 -72.7(8) . . . . ?
C19 C14 C15 C16 1.1(7) . . . . ?
C20 C17 C18 C19 178.3(5) . . . . ?

_olex2_date_sample_data_collection 2015-04-28
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_heyt_0409
_database_code_depnum_ccdc_archive 'CCDC 1407789'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_audit_creation_date             2015-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H10 F3 N O'
_chemical_formula_sum            'C14 H10 F3 N O'
_chemical_formula_weight         265.23
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   9.2351(7)
_cell_length_b                   5.3558(4)
_cell_length_c                   12.9094(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.113(7)
_cell_angle_gamma                90.00
_cell_volume                     619.25(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    648
_cell_measurement_temperature    293.42(10)
_cell_measurement_theta_max      24.3150
_cell_measurement_theta_min      4.1320
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2378
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.48
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00    3.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   90.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega    9.00   47.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -180.0000 19
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0113812000
_diffrn_orient_matrix_UB_12      -0.0462482000
_diffrn_orient_matrix_UB_13      -0.0528684000
_diffrn_orient_matrix_UB_21      -0.0747579000
_diffrn_orient_matrix_UB_22      0.0434176000
_diffrn_orient_matrix_UB_23      -0.0117396000
_diffrn_orient_matrix_UB_31      0.0234100000
_diffrn_orient_matrix_UB_32      0.1163322000
_diffrn_orient_matrix_UB_33      -0.0165971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1339
_reflns_number_total             1934
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.2822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1470
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F -0.4304(4) -0.0437(11) -1.1142(3) 0.161(2) Uani 1 d . . .
F2 F -0.4568(5) -0.4120(13) -1.0817(3) 0.196(3) Uani 1 d . . .
F3 F -0.3747(4) -0.3105(10) -1.2111(2) 0.1305(16) Uani 1 d . . .
O1 O -0.2805(4) 0.0357(7) -0.3764(2) 0.0729(10) Uani 1 d . . .
N1 N -0.1242(4) -0.0318(9) -1.0326(3) 0.0727(12) Uani 1 d . . .
C1 C -0.1820(4) 0.1375(9) -0.5283(3) 0.0552(11) Uani 1 d . . .
H1 H -0.1260 0.2696 -0.4925 0.066 Uiso 1 calc . . R
C2 C -0.2673(5) -0.0017(9) -0.4786(3) 0.0587(12) Uani 1 d . . .
C3 C -0.3516(5) -0.2003(9) -0.5311(4) 0.0622(14) Uani 1 d . . .
H3 H -0.4111 -0.2912 -0.4960 0.075 Uiso 1 calc . . R
C4 C -0.3487(5) -0.2640(11) -0.6324(3) 0.0607(12) Uani 1 d . . .
H4 H -0.4036 -0.4001 -0.6654 0.073 Uiso 1 calc . . R
C5 C -0.2617(4) -0.1224(8) -0.6878(3) 0.0481(10) Uani 1 d . . .
C6 C -0.1781(4) 0.0817(8) -0.6348(3) 0.0503(10) Uani 1 d . . .
C7 C -0.0924(5) 0.2249(10) -0.6911(3) 0.0603(12) Uani 1 d . . .
H7 H -0.0360 0.3584 -0.6569 0.072 Uiso 1 calc . . R
C8 C -0.0912(5) 0.1710(9) -0.7935(3) 0.0612(12) Uani 1 d . . .
H8 H -0.0370 0.2699 -0.8297 0.073 Uiso 1 calc . . R
C9 C -0.1731(4) -0.0370(9) -0.8452(3) 0.0508(11) Uani 1 d . . .
C10 C -0.2554(4) -0.1775(8) -0.7930(3) 0.0540(12) Uani 1 d . . .
H10 H -0.3088 -0.3132 -0.8277 0.065 Uiso 1 calc . . R
C11 C -0.1714(4) -0.0974(9) -0.9538(3) 0.0530(11) Uani 1 d . . .
C12 C -0.2177(5) -0.2703(10) -1.0416(3) 0.0606(12) Uani 1 d . . .
H12 H -0.1641 -0.4296 -1.0363 0.073 Uiso 1 calc . . R
C13 C -0.3673(5) -0.2619(14) -1.1123(3) 0.0723(15) Uani 1 d . . .
C14 C -0.2027(7) 0.2397(12) -0.3171(4) 0.0855(16) Uani 1 d . . .
H14A H -0.2393 0.3937 -0.3518 0.128 Uiso 1 calc . . GR
H14B H -0.0979 0.2246 -0.3132 0.128 Uiso 1 calc . . GR
H14C H -0.2183 0.2384 -0.2463 0.128 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.304(8) . ?
F2 C13 1.282(7) . ?
F3 C13 1.287(5) . ?
O1 C2 1.369(5) . ?
O1 C14 1.424(6) . ?
N1 C11 1.251(5) . ?
N1 C12 1.531(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.354(5) . ?
C1 C6 1.417(5) . ?
C2 C3 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.418(6) . ?
C5 C6 1.414(5) . ?
C5 C10 1.405(5) . ?
C6 C7 1.423(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.356(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.418(6) . ?
C9 C10 1.359(5) . ?
C9 C11 1.443(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.445(6) . ?
C12 H12 0.9800 . ?
C12 C13 1.459(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C2 O1 C14 118.6(4) . . ?
C11 N1 C12 61.6(3) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.9(4) . . ?
C6 C1 H1 120.0 . . ?
O1 C2 C3 114.2(4) . . ?
C1 C2 O1 125.1(4) . . ?
C1 C2 C3 120.7(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(5) . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 118.6(4) . . ?
C10 C5 C4 122.5(4) . . ?
C10 C5 C6 118.9(4) . . ?
C1 C6 C7 122.1(4) . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 C7 118.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.7(4) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C11 120.1(4) . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 C11 119.8(4) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 C5 121.5(4) . . ?
C9 C10 H10 119.2 . . ?
N1 C11 C9 144.7(5) . . ?
N1 C11 C12 68.7(3) . . ?
C9 C11 C12 146.6(4) . . ?
N1 C12 H12 117.1 . . ?
C11 C12 N1 49.6(3) . . ?
C11 C12 H12 117.1 . . ?
C11 C12 C13 121.6(4) . . ?
C13 C12 N1 116.9(5) . . ?
C13 C12 H12 117.1 . . ?
F1 C13 C12 113.0(5) . . ?
F2 C13 F1 104.4(5) . . ?
F2 C13 F3 107.2(5) . . ?
F2 C13 C12 111.8(5) . . ?
F3 C13 F1 104.3(5) . . ?
F3 C13 C12 115.3(4) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O1 C2 C3 C4 -178.9(4) . . . . ?
N1 C11 C12 C13 -100.0(5) . . . . ?
N1 C12 C13 F1 -33.8(6) . . . . ?
N1 C12 C13 F2 -151.2(5) . . . . ?
N1 C12 C13 F3 86.0(7) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C1 C6 C7 C8 -179.2(4) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C2 C1 C6 C7 178.9(4) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C3 C4 C5 C10 -179.3(4) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C4 C5 C6 C7 -179.3(4) . . . . ?
C4 C5 C10 C9 179.0(4) . . . . ?
C5 C6 C7 C8 0.8(6) . . . . ?
C6 C1 C2 O1 -179.6(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C6 C5 C10 C9 -1.1(6) . . . . ?
C6 C7 C8 C9 -2.0(7) . . . . ?
C7 C8 C9 C10 1.7(6) . . . . ?
C7 C8 C9 C11 -179.4(4) . . . . ?
C8 C9 C10 C5 -0.1(6) . . . . ?
C8 C9 C11 N1 -2.4(9) . . . . ?
C8 C9 C11 C12 175.3(6) . . . . ?
C9 C11 C12 N1 -178.6(8) . . . . ?
C9 C11 C12 C13 81.4(9) . . . . ?
C10 C5 C6 C1 -179.2(4) . . . . ?
C10 C5 C6 C7 0.8(5) . . . . ?
C10 C9 C11 N1 176.5(6) . . . . ?
C10 C9 C11 C12 -5.8(9) . . . . ?
C11 N1 C12 C13 109.9(5) . . . . ?
C11 C9 C10 C5 -179.0(4) . . . . ?
C11 C12 C13 F1 23.5(7) . . . . ?
C11 C12 C13 F2 -94.0(7) . . . . ?
C11 C12 C13 F3 143.3(6) . . . . ?
C12 N1 C11 C9 178.6(8) . . . . ?
C14 O1 C2 C1 1.8(6) . . . . ?
C14 O1 C2 C3 -177.9(4) . . . . ?

_olex2_date_sample_data_collection 2015-04-09
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wangq0518
_database_code_depnum_ccdc_archive 'CCDC 1407790'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_audit_creation_date             2015-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 F3 N O'
_chemical_formula_sum            'C15 H10 F3 N O'
_chemical_formula_weight         277.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.226(3)
_cell_length_b                   13.605(4)
_cell_length_c                   7.270(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.84(2)
_cell_angle_gamma                90.00
_cell_volume                     1306.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    665
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      22.1390
_cell_measurement_theta_min      4.0760
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1576
_diffrn_reflns_av_unetI/netI     0.1566
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8091
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00   37.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000    0.0000 15

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   23.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 12

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   86.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   19.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   24.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  150.0000 16

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   63.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -99.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   42.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   77.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  178.0000  -90.0000 14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0345076000
_diffrn_orient_matrix_UB_12      0.0127301000
_diffrn_orient_matrix_UB_13      0.0676844000
_diffrn_orient_matrix_UB_21      -0.0247523000
_diffrn_orient_matrix_UB_22      -0.0459124000
_diffrn_orient_matrix_UB_23      -0.0126971000
_diffrn_orient_matrix_UB_31      0.0329283000
_diffrn_orient_matrix_UB_32      -0.0210519000
_diffrn_orient_matrix_UB_33      0.0693409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                887
_reflns_number_total             2559
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2202
_refine_ls_R_factor_gt           0.1085
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1865P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2646
_refine_ls_wR_factor_ref         0.3752
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.8740(3) 0.7317(3) 0.5024(7) 0.0934(16) Uani 1 d . . .
F2 F 0.9567(4) 0.6188(4) 0.3730(8) 0.1170(19) Uani 1 d . . .
F3 F 1.0323(3) 0.7203(3) 0.5561(7) 0.1005(17) Uani 1 d . . .
O1 O 0.3157(3) 0.6505(3) 0.2388(6) 0.0591(13) Uani 1 d . . .
N1 N 0.8527(5) 0.4743(5) 1.0585(11) 0.082(2) Uani 1 d . . .
C1 C 0.7431(4) 0.5975(4) 0.6847(8) 0.0393(13) Uani 1 d . . .
C2 C 0.7117(4) 0.5758(4) 0.5066(9) 0.0444(14) Uani 1 d . . .
H2 H 0.7573 0.5481 0.4282 0.053 Uiso 1 calc . . R
C3 C 0.6098(4) 0.5950(3) 0.4391(8) 0.0415(14) Uani 1 d . . .
C4 C 0.5425(4) 0.6388(3) 0.5586(8) 0.0389(14) Uani 1 d . . .
C5 C 0.5768(4) 0.6596(4) 0.7441(8) 0.0421(14) Uani 1 d . . .
H5 H 0.5323 0.6870 0.8250 0.051 Uiso 1 calc . . R
C6 C 0.6737(4) 0.6399(4) 0.8033(9) 0.0465(15) Uani 1 d . . .
H6 H 0.6948 0.6547 0.9241 0.056 Uiso 1 calc . . R
C7 C 0.4400(3) 0.6566(4) 0.4965(8) 0.0425(14) Uani 1 d . . .
H7 H 0.3940 0.6824 0.5762 0.051 Uiso 1 calc . . R
C8 C 0.4102(4) 0.6348(4) 0.3157(8) 0.0439(15) Uani 1 d . . .
C9 C 0.4780(4) 0.5921(4) 0.1991(9) 0.0475(15) Uani 1 d . . .
H9 H 0.4565 0.5767 0.0788 0.057 Uiso 1 calc . . R
C10 C 0.5744(4) 0.5726(4) 0.2569(8) 0.0481(15) Uani 1 d . . .
H10 H 0.6181 0.5441 0.1760 0.058 Uiso 1 calc . . R
C11 C 0.2414(4) 0.6932(5) 0.3533(11) 0.075(2) Uani 1 d . . .
H11A H 0.1784 0.7004 0.2832 0.113 Uiso 1 calc . . GR
H11B H 0.2645 0.7565 0.3961 0.113 Uiso 1 calc . . GR
H11C H 0.2318 0.6511 0.4570 0.113 Uiso 1 calc . . GR
C12 C 0.8463(4) 0.5744(4) 0.7572(9) 0.0538(17) Uani 1 d . . .
C13 C 0.9347(5) 0.6016(5) 0.6918(11) 0.0621(19) Uani 1 d . . .
H13 H 0.9931 0.5772 0.7518 0.075 Uiso 1 calc . . R
C14 C 0.9480(4) 0.6676(6) 0.5317(13) 0.075(2) Uani 1 d . . .
C15 C 0.8520(5) 0.5179(5) 0.9259(13) 0.066(2) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.320(7) . ?
F2 C14 1.341(9) . ?
F3 C14 1.331(7) . ?
O1 C8 1.361(6) . ?
O1 C11 1.441(8) . ?
N1 C15 1.132(9) . ?
C1 C2 1.372(8) . ?
C1 C6 1.414(8) . ?
C1 C12 1.472(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.435(7) . ?
C3 C4 1.407(8) . ?
C3 C10 1.416(8) . ?
C4 C5 1.430(8) . ?
C4 C7 1.429(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.358(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.385(8) . ?
C8 C9 1.392(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.348(7) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.336(9) . ?
C12 C15 1.446(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.487(11) . ?

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
C8 O1 C11 117.7(5) . . ?
C2 C1 C6 119.2(4) . . ?
C2 C1 C12 121.6(5) . . ?
C6 C1 C12 119.2(5) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 118.6(5) . . ?
C4 C3 C10 118.6(5) . . ?
C10 C3 C2 122.9(5) . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 C7 119.8(5) . . ?
C7 C4 C5 121.0(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C4 C7 H7 120.5 . . ?
C8 C7 C4 119.0(5) . . ?
C8 C7 H7 120.5 . . ?
O1 C8 C7 124.7(5) . . ?
O1 C8 C9 115.0(5) . . ?
C9 C8 C7 120.4(5) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(5) . . ?
C10 C9 H9 119.3 . . ?
C3 C10 H10 119.5 . . ?
C9 C10 C3 120.9(6) . . ?
C9 C10 H10 119.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 128.7(6) . . ?
C13 C12 C15 116.0(6) . . ?
C15 C12 C1 115.2(6) . . ?
C12 C13 H13 117.1 . . ?
C12 C13 C14 125.8(6) . . ?
C14 C13 H13 117.1 . . ?
F1 C14 F2 106.5(6) . . ?
F1 C14 F3 106.0(6) . . ?
F1 C14 C13 114.2(6) . . ?
F2 C14 C13 113.1(6) . . ?
F3 C14 F2 105.9(7) . . ?
F3 C14 C13 110.6(6) . . ?
N1 C15 C12 177.4(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 C8 C9 C10 179.8(5) . . . . ?
C1 C2 C3 C4 1.3(8) . . . . ?
C1 C2 C3 C10 -179.3(5) . . . . ?
C1 C12 C13 C14 3.4(11) . . . . ?
C1 C12 C15 N1 -10(17) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C2 C1 C12 C13 55.8(9) . . . . ?
C2 C1 C12 C15 -127.0(6) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C2 C3 C4 C7 -178.5(5) . . . . ?
C2 C3 C10 C9 -179.9(5) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
C3 C4 C7 C8 -3.3(8) . . . . ?
C4 C3 C10 C9 -0.5(8) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C4 C7 C8 O1 -178.3(4) . . . . ?
C4 C7 C8 C9 2.9(8) . . . . ?
C5 C4 C7 C8 -179.7(5) . . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
C6 C1 C12 C13 -126.4(7) . . . . ?
C6 C1 C12 C15 50.8(7) . . . . ?
C7 C4 C5 C6 178.2(5) . . . . ?
C7 C8 C9 C10 -1.3(8) . . . . ?
C8 C9 C10 C3 0.0(9) . . . . ?
C10 C3 C4 C5 178.6(5) . . . . ?
C10 C3 C4 C7 2.1(7) . . . . ?
C11 O1 C8 C7 0.2(8) . . . . ?
C11 O1 C8 C9 179.1(5) . . . . ?
C12 C1 C2 C3 177.5(5) . . . . ?
C12 C1 C6 C5 -177.9(5) . . . . ?
C12 C13 C14 F1 27.9(11) . . . . ?
C12 C13 C14 F2 -94.1(8) . . . . ?
C12 C13 C14 F3 147.4(7) . . . . ?
C13 C12 C15 N1 168(17) . . . . ?
C15 C12 C13 C14 -173.8(6) . . . . ?

_olex2_date_sample_data_collection 2015-05-18
_olex2_submission_special_instructions 'No special instructions were received'
