# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_NM30
_database_code_depnum_ccdc_archive 'CCDC 1027431'
_audit_update_record             
;
2014-10-03 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 F3 N O'
_chemical_formula_sum            'C15 H12 F3 N O'
_chemical_formula_weight         279.26

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.731(5)
_cell_length_b                   8.3394(15)
_cell_length_c                   13.706(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.707(12)
_cell_angle_gamma                90.00
_cell_volume                     2597.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5413
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      22.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4556
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_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         0.90
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4556
_reflns_number_gt                3759
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          Twin

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.5571P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4556
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    NM30 in P2(1)/c
CELL 0.71073 23.7307 8.3394 13.7061 90.000 106.707 90.000
ZERR 8.00 0.0049 0.0015 0.0024 0.000 0.012 0.000
LATT  1
SYMM -X, 0.50000+Y, 0.50000-Z
SFAC    C   H   N   O   F
UNIT   120  96   8   8  24
MERG    0
L.S.    12
TEMP -153
SIZE 0.43 0.31 0.14
ACTA
BOND $H
HTAB
CONF
FMAP    2
PLAN    5
WGHT    0.035700    0.557100
BASF   0.41113
FVAR      10.28691
F1    5    0.460072    0.086258    0.912509    11.00000    0.04376    0.02758 =
         0.04648    0.00424   -0.00269   -0.00458
F2    5    0.473094    0.248261    1.039469    11.00000    0.05398    0.04794 =
         0.02916    0.01095    0.01535    0.00929
F3    5    0.538557    0.226721    0.959354    11.00000    0.02700    0.03859 =
         0.03803    0.00126    0.00325    0.00206
F1'   5    0.028122    0.751833    0.569407    11.00000    0.04944    0.05080 =
         0.02498   -0.00583    0.00997    0.01065
F2'   5   -0.036975    0.774852    0.424408    11.00000    0.03027    0.03658 =
         0.03679    0.00098    0.01281    0.00296
F3'   5    0.042071    0.912607    0.455388    11.00000    0.04413    0.02608 =
         0.06120   -0.00916    0.02414   -0.00616
N1    3    0.362466    0.705327    0.662702    11.00000    0.03442    0.01948 =
         0.02426    0.00184    0.00956    0.00040
O1    4    0.317979    0.782680    0.500547    11.00000    0.05002    0.03038 =
         0.03124    0.01373    0.01231    0.00867
N1'   3    0.135279    0.285577    0.300463    11.00000    0.03314    0.01747 =
         0.02526    0.00166    0.00842    0.00403
O1'   4    0.181842    0.205068    0.186947    11.00000    0.04776    0.02705 =
         0.03234   -0.00324    0.01461    0.00431
C1    1    0.320583    0.503118    0.530033    11.00000    0.02374    0.02468 =
         0.02920   -0.00019    0.00198    0.00577
C2    1    0.327325    0.457958    0.436219    11.00000    0.03390    0.03810 =
         0.02751    0.00210    0.00644    0.01051
AFIX  43
H2    2    0.342387    0.532653    0.397728    11.00000   -1.20000
AFIX   0
C3    1    0.312310    0.305824    0.398922    11.00000    0.03704    0.04146 =
         0.03699   -0.01110   -0.00203    0.01568
AFIX  43
H3    2    0.317165    0.275537    0.335008    11.00000   -1.20000
AFIX   0
C4    1    0.290289    0.197793    0.454221    11.00000    0.02857    0.03377 =
         0.06315   -0.02169   -0.00207    0.00443
AFIX  43
H4    2    0.280302    0.092510    0.428602    11.00000   -1.20000
AFIX   0
C5    1    0.282562    0.241086    0.546770    11.00000    0.02451    0.03526 =
         0.06876    0.00044    0.01460   -0.00311
AFIX  43
H5    2    0.266750    0.166596    0.584313    11.00000   -1.20000
AFIX   0
C6    1    0.297965    0.393128    0.584209    11.00000    0.02747    0.02940 =
         0.03813   -0.00031    0.01099    0.00196
AFIX  43
H6    2    0.292975    0.422796    0.648132    11.00000   -1.20000
AFIX   0
C7    1    0.393132    0.588532    0.734764    11.00000    0.02824    0.02175 =
         0.02428   -0.00051    0.00846   -0.00126
C8    1    0.430771    0.480182    0.709591    11.00000    0.03008    0.02919 =
         0.02563    0.00316    0.01126    0.00065
AFIX  43
H8    2    0.437249    0.484893    0.644401    11.00000   -1.20000
AFIX   0
C9    1    0.458882    0.365524    0.778693    11.00000    0.02547    0.02847 =
         0.02988   -0.00146    0.00834    0.00281
AFIX  43
H9    2    0.483695    0.289018    0.760314    11.00000   -1.20000
AFIX   0
C10   1    0.451071    0.361421    0.875051    11.00000    0.02586    0.02129 =
         0.02538    0.00013    0.00418   -0.00241
C11   1    0.414409    0.471992    0.901047    11.00000    0.02743    0.02785 =
         0.02272   -0.00369    0.00850   -0.00831
AFIX  43
H11   2    0.409248    0.469611    0.967245    11.00000   -1.20000
AFIX   0
C12   1    0.385213    0.585917    0.831592    11.00000    0.02815    0.02380 =
         0.02924   -0.00424    0.01035   -0.00232
AFIX  43
H12   2    0.360021    0.661610    0.849678    11.00000   -1.20000
AFIX   0
C13   1    0.334217    0.672331    0.563013    11.00000    0.02846    0.03020 =
         0.02623    0.00348    0.01078    0.00262
C14   1    0.366493    0.873970    0.693750    11.00000    0.05164    0.02330 =
         0.03867   -0.00480    0.01137    0.00105
AFIX 137
H14A  2    0.374015    0.940268    0.639792    11.00000   -1.50000
H14B  2    0.398744    0.887287    0.756562    11.00000   -1.50000
H14C  2    0.329415    0.907205    0.705673    11.00000   -1.50000
AFIX   0
C15   1    0.480264    0.232961    0.947112    11.00000    0.03096    0.03040 =
         0.02975    0.00124    0.00928   -0.00229
C1'   1    0.180227    0.484865    0.213199    11.00000    0.02105    0.02791 =
         0.02718   -0.00269    0.00721    0.00340
C2'   1    0.201907    0.593873    0.291602    11.00000    0.02168    0.03293 =
         0.03853   -0.00696    0.00792    0.00005
AFIX  43
H2'   2    0.206925    0.563053    0.360306    11.00000   -1.20000
AFIX   0
C3'   1    0.216265    0.748804    0.268900    11.00000    0.02849    0.02627 =
         0.06507   -0.00780    0.01313   -0.00359
AFIX  43
H3'   2    0.231297    0.823772    0.322231    11.00000   -1.20000
AFIX   0
C4'   1    0.208670    0.793104    0.169337    11.00000    0.03076    0.03130 =
         0.07230    0.00997    0.01621    0.00024
AFIX  43
H4'   2    0.217307    0.899892    0.154210    11.00000   -1.20000
AFIX   0
C5'   1    0.188809    0.685234    0.091667    11.00000    0.03897    0.04091 =
         0.05119    0.01670    0.01867    0.00817
AFIX  43
H5'   2    0.184630    0.716418    0.023283    11.00000   -1.20000
AFIX   0
C6'   1    0.174933    0.531508    0.113089    11.00000    0.03337    0.03391 =
         0.03297    0.00289    0.01158    0.00801
AFIX  43
H6'   2    0.161626    0.456385    0.059264    11.00000   -1.20000
AFIX   0
C7'   1    0.106295    0.404835    0.342876    11.00000    0.02416    0.01949 =
         0.02826   -0.00109    0.00762   -0.00151
C8'   1    0.115176    0.411931    0.446971    11.00000    0.02926    0.02422 =
         0.02165    0.00494    0.00470    0.00210
AFIX  43
H8'   2    0.140875    0.337168    0.490073    11.00000   -1.20000
AFIX   0
C9'   1    0.086982    0.527055    0.489325    11.00000    0.03451    0.02627 =
         0.02189    0.00065    0.00806   -0.00261
AFIX  43
H9'   2    0.092926    0.530282    0.560863    11.00000   -1.20000
AFIX   0
C10'  1    0.050118    0.637120    0.426311    11.00000    0.02367    0.02458 =
         0.02247   -0.00011    0.00615   -0.00120
C11'  1    0.040677    0.629940    0.321472    11.00000    0.02362    0.02654 =
         0.02668    0.00075    0.00424    0.00564
AFIX  43
H11'  2    0.015306    0.705446    0.278455    11.00000   -1.20000
AFIX   0
C12'  1    0.068003    0.513611    0.279654    11.00000    0.03139    0.02954 =
         0.01891   -0.00065    0.00357    0.00161
AFIX  43
H12'  2    0.060751    0.507586    0.207882    11.00000   -1.20000
AFIX   0
C13'  1    0.165807    0.315015    0.231192    11.00000    0.02752    0.02465 =
         0.01914   -0.00033    0.00003    0.00460
C14'  1    0.126357    0.116722    0.323982    11.00000    0.04665    0.02180 =
         0.03543    0.00139    0.00992    0.00300
AFIX 137
H14D  2    0.104489    0.061258    0.261537    11.00000   -1.50000
H14E  2    0.104007    0.111824    0.373929    11.00000   -1.50000
H14F  2    0.164643    0.064774    0.352122    11.00000   -1.50000
AFIX   0
C15'  1    0.021369    0.766429    0.468702    11.00000    0.02731    0.02730 =
         0.03036   -0.00111    0.01062   -0.00160
HKLF   5
 
REM     NM30 in P2(1)/c
REM R1 =  0.0403 for   3759 Fo > 4sig(Fo)  and  0.0522 for all   4556 data
REM    364 parameters refined using      0 restraints
 
END  
     
WGHT      0.0358      0.5514 
REM Highest difference peak  0.223,  deepest hole -0.182,  1-sigma level  0.043
Q1    1   0.1208  0.3540  0.3212  11.00000  0.05    0.22
Q2    1   0.2994  0.1397  0.6631  11.00000  0.05    0.19
Q3    1   0.4317  0.1487  0.8197  11.00000  0.05    0.17
Q4    1   0.4218  1.0679  0.7393  11.00000  0.05    0.17
Q5    1   0.0699  0.4152  0.2999  11.00000  0.05    0.17
;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.46007(7) 0.08626(18) 0.91251(14) 0.0425(5) Uani 1 1 d . . .
F2 F 0.47309(10) 0.2483(2) 1.03947(15) 0.0430(6) Uani 1 1 d . . .
F3 F 0.53856(7) 0.22672(19) 0.95935(15) 0.0358(5) Uani 1 1 d . . .
F1' F 0.02812(10) 0.75183(18) 0.56941(15) 0.0419(6) Uani 1 1 d . . .
F2' F -0.03698(7) 0.77485(18) 0.42441(15) 0.0339(5) Uani 1 1 d . . .
F3' F 0.04207(7) 0.91261(18) 0.45539(13) 0.0419(5) Uani 1 1 d . . .
N1 N 0.36247(10) 0.7053(3) 0.66270(18) 0.0258(6) Uani 1 1 d . . .
O1 O 0.31798(9) 0.7827(2) 0.50055(17) 0.0371(6) Uani 1 1 d . . .
N1' N 0.13528(10) 0.2856(3) 0.30046(18) 0.0253(6) Uani 1 1 d . . .
O1' O 0.18184(9) 0.2051(2) 0.18695(16) 0.0351(5) Uani 1 1 d . . .
C1 C 0.32058(11) 0.5031(3) 0.5300(2) 0.0270(7) Uani 1 1 d . . .
C2 C 0.32733(12) 0.4580(3) 0.4362(2) 0.0337(7) Uani 1 1 d . . .
H2 H 0.3424 0.5327 0.3977 0.040 Uiso 1 1 calc R . .
C3 C 0.31231(13) 0.3058(4) 0.3989(3) 0.0411(8) Uani 1 1 d . . .
H3 H 0.3172 0.2755 0.3350 0.049 Uiso 1 1 calc R . .
C4 C 0.29029(14) 0.1978(4) 0.4542(3) 0.0450(9) Uani 1 1 d . . .
H4 H 0.2803 0.0925 0.4286 0.054 Uiso 1 1 calc R . .
C5 C 0.28256(15) 0.2411(4) 0.5468(3) 0.0426(11) Uani 1 1 d . . .
H5 H 0.2667 0.1666 0.5843 0.051 Uiso 1 1 calc R . .
C6 C 0.29796(11) 0.3931(3) 0.5842(2) 0.0313(7) Uani 1 1 d . . .
H6 H 0.2930 0.4228 0.6481 0.038 Uiso 1 1 calc R . .
C7 C 0.39313(12) 0.5885(3) 0.7348(2) 0.0246(6) Uani 1 1 d . . .
C8 C 0.43077(11) 0.4802(3) 0.7096(2) 0.0276(7) Uani 1 1 d . . .
H8 H 0.4372 0.4849 0.6444 0.033 Uiso 1 1 calc R . .
C9 C 0.45888(11) 0.3655(3) 0.7787(2) 0.0279(7) Uani 1 1 d . . .
H9 H 0.4837 0.2890 0.7603 0.033 Uiso 1 1 calc R . .
C10 C 0.45107(11) 0.3614(3) 0.8751(2) 0.0248(7) Uani 1 1 d . . .
C11 C 0.41441(11) 0.4720(3) 0.90105(19) 0.0257(6) Uani 1 1 d . . .
H11 H 0.4092 0.4696 0.9672 0.031 Uiso 1 1 calc R . .
C12 C 0.38521(11) 0.5859(3) 0.83159(19) 0.0266(6) Uani 1 1 d . . .
H12 H 0.3600 0.6616 0.8497 0.032 Uiso 1 1 calc R . .
C13 C 0.33422(11) 0.6723(3) 0.5630(2) 0.0277(7) Uani 1 1 d . . .
C14 C 0.36649(13) 0.8740(3) 0.6938(2) 0.0382(8) Uani 1 1 d . . .
H14A H 0.3740 0.9403 0.6398 0.057 Uiso 1 1 calc R . .
H14B H 0.3987 0.8873 0.7566 0.057 Uiso 1 1 calc R . .
H14C H 0.3294 0.9072 0.7057 0.057 Uiso 1 1 calc R . .
C15 C 0.48026(16) 0.2330(3) 0.9471(3) 0.0303(8) Uani 1 1 d . . .
C1' C 0.18023(11) 0.4849(3) 0.2132(2) 0.0253(6) Uani 1 1 d . . .
C2' C 0.20191(11) 0.5939(3) 0.2916(2) 0.0312(7) Uani 1 1 d . . .
H2' H 0.2069 0.5631 0.3603 0.037 Uiso 1 1 calc R . .
C3' C 0.21626(15) 0.7488(3) 0.2689(3) 0.0400(10) Uani 1 1 d . . .
H3' H 0.2313 0.8238 0.3222 0.048 Uiso 1 1 calc R . .
C4' C 0.20867(14) 0.7931(4) 0.1693(3) 0.0445(9) Uani 1 1 d . . .
H4' H 0.2173 0.8999 0.1542 0.053 Uiso 1 1 calc R . .
C5' C 0.18881(13) 0.6852(4) 0.0917(3) 0.0425(8) Uani 1 1 d . . .
H5' H 0.1846 0.7164 0.0233 0.051 Uiso 1 1 calc R . .
C6' C 0.17493(12) 0.5315(3) 0.1131(2) 0.0330(7) Uani 1 1 d . . .
H6' H 0.1616 0.4564 0.0593 0.040 Uiso 1 1 calc R . .
C7' C 0.10629(11) 0.4048(3) 0.3429(2) 0.0240(6) Uani 1 1 d . . .
C8' C 0.11518(11) 0.4119(3) 0.44697(18) 0.0256(6) Uani 1 1 d . . .
H8' H 0.1409 0.3372 0.4901 0.031 Uiso 1 1 calc R . .
C9' C 0.08698(11) 0.5271(3) 0.4893(2) 0.0276(6) Uani 1 1 d . . .
H9' H 0.0929 0.5303 0.5609 0.033 Uiso 1 1 calc R . .
C10' C 0.05012(11) 0.6371(3) 0.4263(2) 0.0237(6) Uani 1 1 d . . .
C11' C 0.04068(11) 0.6299(3) 0.32147(19) 0.0262(6) Uani 1 1 d . . .
H11' H 0.0153 0.7054 0.2785 0.031 Uiso 1 1 calc R . .
C12' C 0.06800(11) 0.5136(3) 0.27965(19) 0.0274(7) Uani 1 1 d . . .
H12' H 0.0608 0.5076 0.2079 0.033 Uiso 1 1 calc R . .
C13' C 0.16581(12) 0.3150(3) 0.2312(2) 0.0252(7) Uani 1 1 d . . .
C14' C 0.12636(13) 0.1167(3) 0.3240(2) 0.0350(8) Uani 1 1 d . . .
H14D H 0.1045 0.0613 0.2615 0.053 Uiso 1 1 calc R . .
H14E H 0.1040 0.1118 0.3739 0.053 Uiso 1 1 calc R . .
H14F H 0.1646 0.0648 0.3521 0.053 Uiso 1 1 calc R . .
C15' C 0.02137(15) 0.7664(3) 0.4687(3) 0.0278(8) 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
F1 C15 1.349(3) . ?
F2 C15 1.331(4) . ?
F3 C15 1.346(4) . ?
F1' C15' 1.349(4) . ?
F2' C15' 1.344(4) . ?
F3' C15' 1.346(3) . ?
N1 C13 1.366(4) . ?
N1 C7 1.428(3) . ?
N1 C14 1.464(3) . ?
O1 C13 1.240(3) . ?
N1' C13' 1.372(4) . ?
N1' C7' 1.425(3) . ?
N1' C14' 1.473(3) . ?
O1' C13' 1.219(3) . ?
C1 C6 1.382(4) . ?
C1 C2 1.393(4) . ?
C1 C13 1.489(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 C12 1.393(4) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C10 C15 1.486(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1' C2' 1.389(4) . ?
C1' C6' 1.397(4) . ?
C1' C13' 1.494(4) . ?
C2' C3' 1.394(4) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.375(5) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.370(5) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.376(4) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C8' 1.382(4) . ?
C7' C12' 1.395(3) . ?
C8' C9' 1.389(4) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.385(3) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.390(4) . ?
C10' C15' 1.481(4) . ?
C11' C12' 1.380(4) . ?
C11' H11' 0.9500 . ?
C12' H12' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?

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
C13 N1 C7 124.1(2) . . ?
C13 N1 C14 117.2(2) . . ?
C7 N1 C14 118.4(2) . . ?
C13' N1' C7' 124.8(2) . . ?
C13' N1' C14' 117.4(2) . . ?
C7' N1' C14' 117.5(2) . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 C13 123.4(2) . . ?
C2 C1 C13 117.7(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C12 120.1(2) . . ?
C8 C7 N1 120.7(2) . . ?
C12 C7 N1 119.2(2) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 C15 121.1(3) . . ?
C9 C10 C15 119.1(3) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
O1 C13 N1 120.4(3) . . ?
O1 C13 C1 119.8(3) . . ?
N1 C13 C1 119.7(2) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F2 C15 F3 107.0(3) . . ?
F2 C15 F1 107.0(3) . . ?
F3 C15 F1 104.9(2) . . ?
F2 C15 C10 113.6(3) . . ?
F3 C15 C10 112.1(3) . . ?
F1 C15 C10 111.7(3) . . ?
C2' C1' C6' 119.1(3) . . ?
C2' C1' C13' 123.0(2) . . ?
C6' C1' C13' 117.8(2) . . ?
C1' C2' C3' 119.6(3) . . ?
C1' C2' H2' 120.2 . . ?
C3' C2' H2' 120.2 . . ?
C4' C3' C2' 120.0(3) . . ?
C4' C3' H3' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C5' C4' C3' 120.8(3) . . ?
C5' C4' H4' 119.6 . . ?
C3' C4' H4' 119.6 . . ?
C4' C5' C6' 119.7(3) . . ?
C4' C5' H5' 120.1 . . ?
C6' C5' H5' 120.1 . . ?
C5' C6' C1' 120.6(3) . . ?
C5' C6' H6' 119.7 . . ?
C1' C6' H6' 119.7 . . ?
C8' C7' C12' 119.5(2) . . ?
C8' C7' N1' 120.2(2) . . ?
C12' C7' N1' 120.3(2) . . ?
C7' C8' C9' 120.8(2) . . ?
C7' C8' H8' 119.6 . . ?
C9' C8' H8' 119.6 . . ?
C10' C9' C8' 119.4(2) . . ?
C10' C9' H9' 120.3 . . ?
C8' C9' H9' 120.3 . . ?
C9' C10' C11' 120.1(2) . . ?
C9' C10' C15' 121.2(3) . . ?
C11' C10' C15' 118.8(3) . . ?
C12' C11' C10' 120.3(2) . . ?
C12' C11' H11' 119.9 . . ?
C10' C11' H11' 119.9 . . ?
C11' C12' C7' 119.9(2) . . ?
C11' C12' H12' 120.0 . . ?
C7' C12' H12' 120.0 . . ?
O1' C13' N1' 120.8(3) . . ?
O1' C13' C1' 120.8(3) . . ?
N1' C13' C1' 118.4(2) . . ?
N1' C14' H14D 109.5 . . ?
N1' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
N1' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
F2' C15' F3' 105.1(2) . . ?
F2' C15' F1' 105.7(3) . . ?
F3' C15' F1' 106.3(2) . . ?
F2' C15' C10' 113.1(3) . . ?
F3' C15' C10' 112.3(3) . . ?
F1' C15' C10' 113.8(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
C6 C1 C2 C3 -0.7(4) . . . . ?
C13 C1 C2 C3 -176.4(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C13 C1 C6 C5 175.7(3) . . . . ?
C13 N1 C7 C8 45.3(4) . . . . ?
C14 N1 C7 C8 -127.9(3) . . . . ?
C13 N1 C7 C12 -135.4(3) . . . . ?
C14 N1 C7 C12 51.4(4) . . . . ?
C12 C7 C8 C9 2.4(4) . . . . ?
N1 C7 C8 C9 -178.3(2) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C8 C9 C10 C15 177.9(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C15 C10 C11 C12 -176.8(2) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
N1 C7 C12 C11 179.4(2) . . . . ?
C7 N1 C13 O1 -166.6(2) . . . . ?
C14 N1 C13 O1 6.7(4) . . . . ?
C7 N1 C13 C1 16.0(4) . . . . ?
C14 N1 C13 C1 -170.7(2) . . . . ?
C6 C1 C13 O1 -133.5(3) . . . . ?
C2 C1 C13 O1 42.0(4) . . . . ?
C6 C1 C13 N1 44.0(4) . . . . ?
C2 C1 C13 N1 -140.6(3) . . . . ?
C11 C10 C15 F2 -7.5(4) . . . . ?
C9 C10 C15 F2 175.3(3) . . . . ?
C11 C10 C15 F3 -129.0(3) . . . . ?
C9 C10 C15 F3 53.8(4) . . . . ?
C11 C10 C15 F1 113.6(3) . . . . ?
C9 C10 C15 F1 -63.6(4) . . . . ?
C6' C1' C2' C3' 1.9(4) . . . . ?
C13' C1' C2' C3' 177.8(3) . . . . ?
C1' C2' C3' C4' 0.3(5) . . . . ?
C2' C3' C4' C5' -2.1(5) . . . . ?
C3' C4' C5' C6' 1.5(5) . . . . ?
C4' C5' C6' C1' 0.8(4) . . . . ?
C2' C1' C6' C5' -2.5(4) . . . . ?
C13' C1' C6' C5' -178.5(2) . . . . ?
C13' N1' C7' C8' -131.0(3) . . . . ?
C14' N1' C7' C8' 56.1(4) . . . . ?
C13' N1' C7' C12' 50.1(4) . . . . ?
C14' N1' C7' C12' -122.8(3) . . . . ?
C12' C7' C8' C9' -0.7(4) . . . . ?
N1' C7' C8' C9' -179.7(2) . . . . ?
C7' C8' C9' C10' -0.8(4) . . . . ?
C8' C9' C10' C11' 1.2(4) . . . . ?
C8' C9' C10' C15' -177.1(2) . . . . ?
C9' C10' C11' C12' -0.1(4) . . . . ?
C15' C10' C11' C12' 178.3(3) . . . . ?
C10' C11' C12' C7' -1.4(4) . . . . ?
C8' C7' C12' C11' 1.8(4) . . . . ?
N1' C7' C12' C11' -179.2(2) . . . . ?
C7' N1' C13' O1' -168.9(2) . . . . ?
C14' N1' C13' O1' 4.0(4) . . . . ?
C7' N1' C13' C1' 12.6(4) . . . . ?
C14' N1' C13' C1' -174.5(2) . . . . ?
C2' C1' C13' O1' -133.9(3) . . . . ?
C6' C1' C13' O1' 42.0(4) . . . . ?
C2' C1' C13' N1' 44.6(4) . . . . ?
C6' C1' C13' N1' -139.5(3) . . . . ?
C9' C10' C15' F2' -129.2(3) . . . . ?
C11' C10' C15' F2' 52.4(4) . . . . ?
C9' C10' C15' F3' 112.2(3) . . . . ?
C11' C10' C15' F3' -66.2(4) . . . . ?
C9' C10' C15' F1' -8.6(4) . . . . ?
C11' C10' C15' F1' 173.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
