# 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_NM02
_database_code_depnum_ccdc_archive 'CCDC 1025677'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 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  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

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

_cell_length_a                   35.8393(17)
_cell_length_b                   10.6270(4)
_cell_length_c                   15.1660(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.399(5)
_cell_angle_gamma                90.00
_cell_volume                     5260.3(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4463
_cell_measurement_theta_min      2.3219
_cell_measurement_theta_max      29.3228

_exptl_crystal_description       'Thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2304
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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            25157
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4632
_reflns_number_gt                3475
_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          
; 
 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. 
;

_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)+(0.0369P)²+3.5159P] 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         4632
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    NM02 in C 1 2/c 1
CELL   0.71073  35.8393  10.6270  15.1660  90.000 114.399  90.000
ZERR    16       0.0017   0.0004   0.0007   0.000   0.005   0.000
LATT  7
SYMM -X,Y, 0.50000-Z
SFAC    C   H   N   O   F
UNIT   240 192  16  16  48
MERG    2
L.S.    12
OMIT -1 50
ACTA
HTAB
BOND $H
CONF
TEMP -153
SIZE 0.38 0.26 0.18
FMAP    2
PLAN    5
WGHT    0.036900    3.515900
FVAR       2.24505   0.50833
F1    5    0.435068    0.321361    0.496483    11.00000    0.04012    0.04440 =
         0.02533    0.00635    0.00887    0.01058
F2    5    0.459840    0.397435    0.402275    11.00000    0.02213    0.05079 =
         0.05528    0.01900    0.00944   -0.00381
F3    5    0.441873    0.203376    0.389931    11.00000    0.02931    0.03690 =
         0.04856   -0.00704    0.00684    0.01253
 
N1    3    0.256439    0.190911    0.131718    11.00000    0.01942    0.03010 =
         0.02109   -0.00255    0.00659   -0.00194
O1    4    0.310991    0.130199    0.102630    11.00000    0.03467    0.03399 =
         0.04102   -0.01009    0.02337   -0.00449
C1    1    0.322576    0.297211    0.214044    11.00000    0.02172    0.02718 =
         0.02329    0.00121    0.01400   -0.00063
C2    1    0.362251    0.264393    0.276246    11.00000    0.02307    0.02146 =
         0.02687    0.00509    0.01371    0.00281
AFIX  43
H2    2    0.371205    0.179822    0.278606    11.00000   -1.20000
AFIX   0
C3    1    0.388775    0.354434    0.334777    11.00000    0.02126    0.02778 =
         0.02033    0.00203    0.01168    0.00144
C4    1    0.376487    0.479259    0.330533    11.00000    0.02498    0.02616 =
         0.02653   -0.00232    0.01190   -0.00225
AFIX  43
H4    2    0.395016    0.541254    0.369754    11.00000   -1.20000
AFIX   0
C5    1    0.336887    0.512033    0.268388    11.00000    0.02773    0.02275 =
         0.03335    0.00108    0.01428    0.00304
AFIX  43
H5    2    0.328142    0.596950    0.265238    11.00000   -1.20000
AFIX   0
C6    1    0.310004    0.421856    0.210900    11.00000    0.01991    0.02918 =
         0.02511    0.00373    0.00975    0.00402
AFIX  43
H6    2    0.282809    0.445020    0.169022    11.00000   -1.20000
AFIX   0
C7    1    0.240926    0.244952    0.196628    11.00000    0.01581    0.02404 =
         0.02602   -0.00008    0.00833   -0.00221
C8    1    0.256980    0.207810    0.292752    11.00000    0.01646    0.02625 =
         0.02699    0.00074    0.00645   -0.00209
AFIX  43
H8    2    0.278491    0.147697    0.316278    11.00000   -1.20000
AFIX   0
C9    1    0.241230    0.259555    0.354185    11.00000    0.02491    0.03708 =
         0.02521   -0.00364    0.00989   -0.00666
AFIX  43
H9    2    0.252170    0.235229    0.420352    11.00000   -1.20000
AFIX   0
C10   1    0.209716    0.346304    0.319747    11.00000    0.02915    0.03079 =
         0.04250   -0.00684    0.02120   -0.00420
AFIX  43
H10   2    0.198973    0.381063    0.362139    11.00000   -1.20000
AFIX   0
C11   1    0.193878    0.382374    0.223934    11.00000    0.02269    0.02898 =
         0.04789    0.00696    0.01684    0.00424
AFIX  43
H11   2    0.172255    0.442115    0.200405    11.00000   -1.20000
AFIX   0
C12   1    0.209401    0.331764    0.161873    11.00000    0.02141    0.03108 =
         0.03171    0.00818    0.00940    0.00050
AFIX  43
H12   2    0.198463    0.356521    0.095799    11.00000   -1.20000
AFIX   0
C13   1    0.296338    0.197912    0.145790    11.00000    0.02548    0.02480 =
         0.02409    0.00452    0.01177    0.00117
C14   1    0.228782    0.104889    0.058109    11.00000    0.02757    0.03740 =
         0.02735   -0.00502    0.00669   -0.00615
AFIX 137
H14A  2    0.241897    0.075917    0.016443    11.00000   -1.50000
H14B  2    0.203257    0.148887    0.018790    11.00000   -1.50000
H14C  2    0.222709    0.032373    0.089900    11.00000   -1.50000
AFIX   0
C15   1    0.430958    0.319439    0.404466    11.00000    0.02436    0.02677 =
         0.02811    0.00320    0.01055    0.00159
PART 1
F1A'  5    0.380655    0.367624    0.083720    21.00000    0.03461    0.02694 =
         0.07585    0.00221    0.02285    0.01120
F2A'  5    0.438470    0.387228    0.201229    21.00000    0.07067    0.02597 =
         0.03534   -0.01169    0.01667    0.00239
F3A'  5    0.436679    0.419073    0.060027    21.00000    0.03919    0.01105 =
         0.03520    0.00535    0.01853   -0.00048
PART 2
F1B'  5    0.378510    0.369040    0.036533   -21.00000    0.04738    0.02876 =
         0.14295    0.01520    0.03192    0.01209
F2B'  5    0.423776    0.386891    0.183459   -21.00000    0.21772    0.03342 =
         0.09187   -0.00525    0.12704   -0.00079
F3B'  5    0.436189    0.418119    0.065168   -21.00000    0.12968    0.04286 =
         0.07989    0.01176    0.07469   -0.00175
PART 0
N1'   3    0.378852   -0.208012    0.088073    11.00000    0.02183    0.02234 =
         0.02423   -0.00187    0.00566   -0.00301
O1'   4    0.347415   -0.089190   -0.046500    11.00000    0.03425    0.03406 =
         0.03066    0.00078   -0.00507   -0.00512
C1'   1    0.409031   -0.007792    0.072589    11.00000    0.02249    0.02254 =
         0.01705    0.00021    0.00755   -0.00044
C2'   1    0.398488    0.118353    0.072128    11.00000    0.02255    0.02562 =
         0.02189    0.00156    0.00894    0.00198
AFIX  43
H2'   2    0.370633    0.142067    0.052282    11.00000   -1.20000
AFIX   0
C3'   1    0.428924    0.208799    0.100814    11.00000    0.03043    0.02317 =
         0.02546    0.00073    0.01643   -0.00042
C4'   1    0.469644    0.176033    0.128017    11.00000    0.02665    0.02461 =
         0.02235   -0.00088    0.01151   -0.00745
AFIX  43
H4'   2    0.490282    0.239050    0.147004    11.00000   -1.20000
AFIX   0
C5'   1    0.479899    0.050758    0.127227    11.00000    0.02203    0.02854 =
         0.02892    0.00206    0.01082   -0.00020
AFIX  43
H5'   2    0.507682    0.027508    0.145211    11.00000   -1.20000
AFIX   0
C6'   1    0.449876   -0.040584    0.100378    11.00000    0.02989    0.02015 =
         0.02248    0.00076    0.01165    0.00341
AFIX  43
H6'   2    0.457180   -0.126601    0.100890    11.00000   -1.20000
AFIX   0
C7'   1    0.406046   -0.215042    0.188905    11.00000    0.02141    0.02471 =
         0.02438   -0.00053    0.01113   -0.00764
C8'   1    0.435664   -0.308468    0.221035    11.00000    0.03072    0.02309 =
         0.02987    0.00196    0.01391   -0.00249
AFIX  43
H8'   2    0.438228   -0.366548    0.176240    11.00000   -1.20000
AFIX   0
C9'   1    0.461462   -0.317090    0.318256    11.00000    0.02811    0.03393 =
         0.03122    0.00882    0.01001   -0.00130
AFIX  43
H9'   2    0.481748   -0.381114    0.340320    11.00000   -1.20000
AFIX   0
C10'  1    0.457722   -0.232727    0.383127    11.00000    0.03106    0.04902 =
         0.02305    0.00370    0.00974   -0.00885
AFIX  43
H10'  2    0.475613   -0.238270    0.449849    11.00000   -1.20000
AFIX   0
C11'  1    0.428038   -0.140090    0.351471    11.00000    0.03532    0.04435 =
         0.02740   -0.00902    0.01798   -0.01054
AFIX  43
H11'  2    0.425424   -0.082515    0.396506    11.00000   -1.20000
AFIX   0
C12'  1    0.402060   -0.131079    0.254027    11.00000    0.02361    0.03090 =
         0.03182   -0.00304    0.01486   -0.00229
AFIX  43
H12'  2    0.381625   -0.067481    0.232164    11.00000   -1.20000
AFIX   0
C13'  1    0.375570   -0.103880    0.033810    11.00000    0.02307    0.02457 =
         0.02561   -0.00342    0.00792    0.00114
C14'  1    0.350292   -0.312703    0.046110    11.00000    0.02632    0.02616 =
         0.03345   -0.00533    0.00746   -0.00735
AFIX 137
H14D  2    0.327147   -0.304853    0.064310    11.00000   -1.50000
H14E  2    0.364452   -0.392591    0.070573    11.00000   -1.50000
H14F  2    0.340199   -0.310597   -0.024583    11.00000   -1.50000
AFIX   0
C15'  1    0.418996    0.343670    0.104427    11.00000    0.04405    0.02492 =
         0.05188    0.00352    0.02913   -0.00047
HKLF   4
 
REM     NM02 in C 1 2/c 1
REM R1 =  0.0417 for   3475 Fo > 4sig(Fo)  and  0.0635 for all   4632 data
REM    391 parameters refined using      0 restraints
 
END  
     
WGHT      0.0369      3.5081 
REM Highest difference peak  0.215,  deepest hole -0.244,  1-sigma level  0.048
Q1    1   0.3469 -0.3754  0.0998  11.00000  0.05    0.22
Q2    1   0.3619 -0.3626 -0.0041  11.00000  0.05    0.21
Q3    1   0.2862 -0.0432 -0.0213  11.00000  0.05    0.20
Q4    1   0.3185 -0.2711  0.0020  11.00000  0.05    0.18
Q5    1   0.3469  0.1360  0.1455  11.00000  0.05    0.18
;

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 0.43507(4) 0.32136(12) 0.49648(8) 0.0382(3) Uani 1 1 d . . .
F2 F 0.45984(4) 0.39744(13) 0.40228(9) 0.0449(4) Uani 1 1 d . . .
F3 F 0.44187(4) 0.20338(12) 0.38993(9) 0.0413(3) Uani 1 1 d . . .
N1 N 0.25644(5) 0.19091(16) 0.13172(11) 0.0241(4) Uani 1 1 d . . .
O1 O 0.31099(4) 0.13020(14) 0.10263(10) 0.0340(4) Uani 1 1 d . . .
C1 C 0.32258(6) 0.29721(19) 0.21404(13) 0.0225(4) Uani 1 1 d . . .
C2 C 0.36225(6) 0.26439(19) 0.27625(13) 0.0227(4) Uani 1 1 d . . .
H2 H 0.3712 0.1798 0.2786 0.027 Uiso 1 1 calc R . .
C3 C 0.38878(6) 0.35443(19) 0.33478(13) 0.0221(4) Uani 1 1 d . . .
C4 C 0.37649(6) 0.4793(2) 0.33053(13) 0.0255(5) Uani 1 1 d . . .
H4 H 0.3950 0.5413 0.3698 0.031 Uiso 1 1 calc R . .
C5 C 0.33689(6) 0.5120(2) 0.26839(14) 0.0274(5) Uani 1 1 d . . .
H5 H 0.3281 0.5970 0.2652 0.033 Uiso 1 1 calc R . .
C6 C 0.31000(6) 0.42186(19) 0.21090(13) 0.0246(5) Uani 1 1 d . . .
H6 H 0.2828 0.4450 0.1690 0.030 Uiso 1 1 calc R . .
C7 C 0.24093(6) 0.24495(19) 0.19663(13) 0.0221(4) Uani 1 1 d . . .
C8 C 0.25698(6) 0.20781(19) 0.29275(13) 0.0241(5) Uani 1 1 d . . .
H8 H 0.2785 0.1477 0.3163 0.029 Uiso 1 1 calc R . .
C9 C 0.24123(6) 0.2596(2) 0.35418(14) 0.0292(5) Uani 1 1 d . . .
H9 H 0.2522 0.2352 0.4204 0.035 Uiso 1 1 calc R . .
C10 C 0.20972(6) 0.3463(2) 0.31975(15) 0.0320(5) Uani 1 1 d . . .
H10 H 0.1990 0.3811 0.3621 0.038 Uiso 1 1 calc R . .
C11 C 0.19388(6) 0.3824(2) 0.22393(16) 0.0324(5) Uani 1 1 d . . .
H11 H 0.1723 0.4421 0.2004 0.039 Uiso 1 1 calc R . .
C12 C 0.20940(6) 0.3318(2) 0.16187(15) 0.0286(5) Uani 1 1 d . . .
H12 H 0.1985 0.3565 0.0958 0.034 Uiso 1 1 calc R . .
C13 C 0.29634(6) 0.19791(19) 0.14579(13) 0.0243(5) Uani 1 1 d . . .
C14 C 0.22878(6) 0.1049(2) 0.05811(14) 0.0323(5) Uani 1 1 d . . .
H14A H 0.2419 0.0759 0.0164 0.048 Uiso 1 1 calc R . .
H14B H 0.2033 0.1489 0.0188 0.048 Uiso 1 1 calc R . .
H14C H 0.2227 0.0324 0.0899 0.048 Uiso 1 1 calc R . .
C15 C 0.43096(6) 0.3194(2) 0.40447(14) 0.0265(5) Uani 1 1 d . . .
F1A' F 0.3807(2) 0.3676(8) 0.0837(12) 0.046(2) Uani 0.51(4) 1 d P A 1
F2A' F 0.4385(3) 0.3872(11) 0.2012(6) 0.046(2) Uani 0.51(4) 1 d P A 1
F3A' F 0.4367(2) 0.4191(7) 0.0600(6) 0.027(2) Uani 0.51(4) 1 d P A 1
F1B' F 0.3785(3) 0.3690(8) 0.037(3) 0.075(5) Uani 0.49(4) 1 d P A 2
F2B' F 0.4238(12) 0.3869(11) 0.1835(16) 0.093(5) Uani 0.49(4) 1 d P A 2
F3B' F 0.4362(3) 0.4181(11) 0.0652(9) 0.074(4) Uani 0.49(4) 1 d P A 2
N1' N 0.37885(5) -0.20801(15) 0.08807(11) 0.0241(4) Uani 1 1 d . . .
O1' O 0.34742(5) -0.08919(14) -0.04650(10) 0.0391(4) Uani 1 1 d . . .
C1' C 0.40903(6) -0.00779(19) 0.07259(12) 0.0209(4) Uani 1 1 d . . .
C2' C 0.39849(6) 0.11835(19) 0.07213(13) 0.0234(4) Uani 1 1 d . . .
H2' H 0.3706 0.1421 0.0523 0.028 Uiso 1 1 calc R . .
C3' C 0.42892(6) 0.20880(19) 0.10081(13) 0.0247(5) Uani 1 1 d . A .
C4' C 0.46964(6) 0.17603(19) 0.12802(13) 0.0241(5) Uani 1 1 d . . .
H4' H 0.4903 0.2390 0.1470 0.029 Uiso 1 1 calc R . .
C5' C 0.47990(6) 0.0508(2) 0.12723(14) 0.0264(5) Uani 1 1 d . . .
H5' H 0.5077 0.0275 0.1452 0.032 Uiso 1 1 calc R . .
C6' C 0.44988(6) -0.04058(19) 0.10038(13) 0.0239(5) Uani 1 1 d . . .
H6' H 0.4572 -0.1266 0.1009 0.029 Uiso 1 1 calc R . .
C7' C 0.40605(6) -0.21504(19) 0.18891(13) 0.0229(4) Uani 1 1 d . . .
C8' C 0.43566(6) -0.30847(19) 0.22103(14) 0.0274(5) Uani 1 1 d . . .
H8' H 0.4382 -0.3665 0.1762 0.033 Uiso 1 1 calc R . .
C9' C 0.46146(6) -0.3171(2) 0.31826(14) 0.0318(5) Uani 1 1 d . . .
H9' H 0.4817 -0.3811 0.3403 0.038 Uiso 1 1 calc R . .
C10' C 0.45772(7) -0.2327(2) 0.38313(15) 0.0349(6) Uani 1 1 d . . .
H10' H 0.4756 -0.2383 0.4498 0.042 Uiso 1 1 calc R . .
C11' C 0.42804(7) -0.1401(2) 0.35147(14) 0.0340(5) Uani 1 1 d . . .
H11' H 0.4254 -0.0825 0.3965 0.041 Uiso 1 1 calc R . .
C12' C 0.40206(6) -0.1311(2) 0.25403(14) 0.0276(5) Uani 1 1 d . . .
H12' H 0.3816 -0.0675 0.2322 0.033 Uiso 1 1 calc R . .
C13' C 0.37557(6) -0.10388(19) 0.03381(14) 0.0251(5) Uani 1 1 d . . .
C14' C 0.35029(6) -0.3127(2) 0.04611(14) 0.0303(5) Uani 1 1 d . . .
H14D H 0.3271 -0.3049 0.0643 0.045 Uiso 1 1 calc R . .
H14E H 0.3645 -0.3926 0.0706 0.045 Uiso 1 1 calc R . .
H14F H 0.3402 -0.3106 -0.0246 0.045 Uiso 1 1 calc R . .
C15' C 0.41900(7) 0.3437(2) 0.10443(18) 0.0372(6) 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 1.342(2) . ?
F2 C15 1.337(2) . ?
F3 C15 1.339(2) . ?
N1 C13 1.358(2) . ?
N1 C7 1.435(2) . ?
N1 C14 1.466(2) . ?
O1 C13 1.227(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.394(3) . ?
C1 C13 1.505(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 C15 1.490(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.383(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
F1A' C15' 1.302(7) . ?
F2A' C15' 1.418(9) . ?
F3A' C15' 1.360(10) . ?
F1B' C15' 1.416(17) . ?
F2B' C15' 1.228(14) . ?
F3B' C15' 1.290(13) . ?
N1' C13' 1.355(3) . ?
N1' C7' 1.436(2) . ?
N1' C14' 1.467(2) . ?
O1' C13' 1.229(2) . ?
C1' C6' 1.390(3) . ?
C1' C2' 1.392(3) . ?
C1' C13' 1.498(3) . ?
C2' C3' 1.382(3) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.387(3) . ?
C3' C15' 1.483(3) . ?
C4' C5' 1.382(3) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.380(3) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C12' 1.382(3) . ?
C7' C8' 1.387(3) . ?
C8' C9' 1.382(3) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.378(3) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.382(3) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.387(3) . ?
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 123.47(16) . . ?
C13 N1 C14 119.38(16) . . ?
C7 N1 C14 116.11(15) . . ?
C2 C1 C6 119.22(19) . . ?
C2 C1 C13 117.71(18) . . ?
C6 C1 C13 122.79(17) . . ?
C3 C2 C1 120.16(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.66(18) . . ?
C2 C3 C15 120.65(18) . . ?
C4 C3 C15 118.68(18) . . ?
C5 C4 C3 119.15(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.39(18) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 120.65(18) . . ?
C12 C7 N1 119.49(17) . . ?
C8 C7 N1 119.84(17) . . ?
C7 C8 C9 119.12(19) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.42(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.01(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.62(19) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O1 C13 N1 122.61(18) . . ?
O1 C13 C1 119.64(17) . . ?
N1 C13 C1 117.69(17) . . ?
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 106.56(16) . . ?
F2 C15 F1 105.24(16) . . ?
F3 C15 F1 105.73(16) . . ?
F2 C15 C3 113.37(16) . . ?
F3 C15 C3 113.13(17) . . ?
F1 C15 C3 112.16(16) . . ?
C13' N1' C7' 122.66(16) . . ?
C13' N1' C14' 119.07(15) . . ?
C7' N1' C14' 117.87(16) . . ?
C6' C1' C2' 119.51(18) . . ?
C6' C1' C13' 121.34(18) . . ?
C2' C1' C13' 118.87(17) . . ?
C3' C2' C1' 119.39(18) . . ?
C3' C2' H2' 120.3 . . ?
C1' C2' H2' 120.3 . . ?
C2' C3' C4' 121.04(19) . . ?
C2' C3' C15' 120.89(19) . . ?
C4' C3' C15' 118.07(19) . . ?
C5' C4' C3' 119.34(19) . . ?
C5' C4' H4' 120.3 . . ?
C3' C4' H4' 120.3 . . ?
C6' C5' C4' 120.15(19) . . ?
C6' C5' H5' 119.9 . . ?
C4' C5' H5' 119.9 . . ?
C5' C6' C1' 120.55(19) . . ?
C5' C6' H6' 119.7 . . ?
C1' C6' H6' 119.7 . . ?
C12' C7' C8' 120.10(18) . . ?
C12' C7' N1' 120.17(18) . . ?
C8' C7' N1' 119.72(17) . . ?
C9' C8' C7' 119.99(19) . . ?
C9' C8' H8' 120.0 . . ?
C7' C8' H8' 120.0 . . ?
C10' C9' C8' 119.9(2) . . ?
C10' C9' H9' 120.0 . . ?
C8' C9' H9' 120.0 . . ?
C9' C10' C11' 120.23(19) . . ?
C9' C10' H10' 119.9 . . ?
C11' C10' H10' 119.9 . . ?
C10' C11' C12' 120.1(2) . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' H11' 120.0 . . ?
C7' C12' C11' 119.7(2) . . ?
C7' C12' H12' 120.2 . . ?
C11' C12' H12' 120.2 . . ?
O1' C13' N1' 122.37(18) . . ?
O1' C13' C1' 119.92(18) . . ?
N1' C13' C1' 117.63(16) . . ?
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 . . ?
F2B' C15' F3B' 108.7(10) . . ?
F3B' C15' F1A' 115.3(8) . . ?
F2B' C15' F3A' 110.9(10) . . ?
F1A' C15' F3A' 115.3(8) . . ?
F2B' C15' F1B' 109.1(7) . . ?
F3B' C15' F1B' 95.1(11) . . ?
F3A' C15' F1B' 94.3(10) . . ?
F3B' C15' F2A' 98.8(7) . . ?
F1A' C15' F2A' 101.8(7) . . ?
F3A' C15' F2A' 100.9(6) . . ?
F1B' C15' F2A' 127.5(13) . . ?
F2B' C15' C3' 117.3(8) . . ?
F3B' C15' C3' 114.1(6) . . ?
F1A' C15' C3' 115.2(4) . . ?
F3A' C15' C3' 112.5(4) . . ?
F1B' C15' C3' 110.3(7) . . ?
F2A' C15' C3' 109.3(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
C6 C1 C2 C3 0.5(3) . . . . ?
C13 C1 C2 C3 174.65(17) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C1 C2 C3 C15 177.75(17) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C15 C3 C4 C5 -177.82(17) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C13 C1 C6 C5 -173.21(17) . . . . ?
C13 N1 C7 C12 122.8(2) . . . . ?
C14 N1 C7 C12 -69.0(2) . . . . ?
C13 N1 C7 C8 -58.6(3) . . . . ?
C14 N1 C7 C8 109.6(2) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
N1 C7 C8 C9 -179.05(17) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
N1 C7 C12 C11 178.85(18) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C7 N1 C13 O1 164.03(18) . . . . ?
C14 N1 C13 O1 -3.8(3) . . . . ?
C7 N1 C13 C1 -18.7(3) . . . . ?
C14 N1 C13 C1 173.44(17) . . . . ?
C2 C1 C13 O1 -43.4(3) . . . . ?
C6 C1 C13 O1 130.5(2) . . . . ?
C2 C1 C13 N1 139.26(18) . . . . ?
C6 C1 C13 N1 -46.8(3) . . . . ?
C2 C3 C15 F2 133.65(18) . . . . ?
C4 C3 C15 F2 -47.0(2) . . . . ?
C2 C3 C15 F3 12.2(3) . . . . ?
C4 C3 C15 F3 -168.49(16) . . . . ?
C2 C3 C15 F1 -107.3(2) . . . . ?
C4 C3 C15 F1 72.0(2) . . . . ?
C6' C1' C2' C3' -1.0(3) . . . . ?
C13' C1' C2' C3' -175.11(16) . . . . ?
C1' C2' C3' C4' 1.4(3) . . . . ?
C1' C2' C3' C15' -177.92(18) . . . . ?
C2' C3' C4' C5' -0.6(3) . . . . ?
C15' C3' C4' C5' 178.71(18) . . . . ?
C3' C4' C5' C6' -0.5(3) . . . . ?
C4' C5' C6' C1' 0.9(3) . . . . ?
C2' C1' C6' C5' -0.1(3) . . . . ?
C13' C1' C6' C5' 173.82(17) . . . . ?
C13' N1' C7' C12' 59.2(3) . . . . ?
C14' N1' C7' C12' -113.5(2) . . . . ?
C13' N1' C7' C8' -122.5(2) . . . . ?
C14' N1' C7' C8' 64.8(2) . . . . ?
C12' C7' C8' C9' -0.5(3) . . . . ?
N1' C7' C8' C9' -178.87(17) . . . . ?
C7' C8' C9' C10' 0.0(3) . . . . ?
C8' C9' C10' C11' 0.5(3) . . . . ?
C9' C10' C11' C12' -0.5(3) . . . . ?
C8' C7' C12' C11' 0.5(3) . . . . ?
N1' C7' C12' C11' 178.90(18) . . . . ?
C10' C11' C12' C7' 0.0(3) . . . . ?
C7' N1' C13' O1' -166.38(18) . . . . ?
C14' N1' C13' O1' 6.2(3) . . . . ?
C7' N1' C13' C1' 16.8(3) . . . . ?
C14' N1' C13' C1' -170.55(17) . . . . ?
C6' C1' C13' O1' -123.0(2) . . . . ?
C2' C1' C13' O1' 50.9(3) . . . . ?
C6' C1' C13' N1' 53.8(2) . . . . ?
C2' C1' C13' N1' -132.18(19) . . . . ?
C2' C3' C15' F2B' 98(2) . . . . ?
C4' C3' C15' F2B' -81(2) . . . . ?
C2' C3' C15' F3B' -133.3(6) . . . . ?
C4' C3' C15' F3B' 47.4(6) . . . . ?
C2' C3' C15' F1A' 3.3(9) . . . . ?
C4' C3' C15' F1A' -176.0(9) . . . . ?
C2' C3' C15' F3A' -131.5(4) . . . . ?
C4' C3' C15' F3A' 49.1(4) . . . . ?
C2' C3' C15' F1B' -27.7(15) . . . . ?
C4' C3' C15' F1B' 153.0(15) . . . . ?
C2' C3' C15' F2A' 117.2(5) . . . . ?
C4' C3' C15' F2A' -62.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_NM03
_database_code_depnum_ccdc_archive 'CCDC 1025678'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 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                   15.1633(5)
_cell_length_b                   9.9603(3)
_cell_length_c                   17.7768(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.269(2)
_cell_angle_gamma                90.00
_cell_volume                     2663.27(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9794
_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            22406
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         27.58
_reflns_number_total             6117
_reflns_number_gt                4629
_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          
; 
 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. 
;

_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)+(0.0635P)²+0.7326P] 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         6117
_refine_ls_number_parameters     395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    NM03 in P 1 21/c 1
CELL   0.71073  15.1633   9.9603  17.7768  90.000  97.269  90.000
ZERR     8       0.0005   0.0003   0.0006   0.000   0.002   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    2
L.S.    12
TEMP -153
SIZE  0.34 0.25 0.18
EADP F1B  F2B  F3B
EADP F1B' F2B' F3B'
ACTA
HTAB
BOND $H
CONF
FMAP    2
PLAN   5
WGHT    0.063500    0.732600
FVAR       0.11993   0.84956   0.90381
PART -1
F1A   5    0.502890   -0.323221    0.260508    21.00000    0.07392    0.07786 =
         0.13315    0.03862   -0.06210   -0.01116
F2A   5    0.387959   -0.433503    0.275298    21.00000    0.08103    0.12512 =
         0.09632    0.08070    0.00977   -0.00045
F3A   5    0.460648   -0.483904    0.187291    21.00000    0.19697    0.12249 =
         0.08850   -0.01256   -0.02261    0.12048
PART -2
F1B   5    0.508332   -0.375817    0.217758   -21.00000    0.05261    0.05898 =
         0.10551    0.03457   -0.01026    0.00022
F2B   5    0.428436   -0.341371    0.302490   -21.00000    0.05261    0.05898 =
         0.10551    0.03457   -0.01026    0.00022
F3B   5    0.419229   -0.496378    0.227322   -21.00000    0.05261    0.05898 =
         0.10551    0.03457   -0.01026    0.00022
PART 0
O1    4    0.114109   -0.079937    0.029508    11.00000    0.03304    0.06037 =
         0.04054    0.00238   -0.00043   -0.00316
N1    3    0.213262    0.079370    0.006005    11.00000    0.03265    0.03947 =
         0.03473    0.00041    0.00273    0.00731
C1    1    0.262194   -0.120959    0.080986    11.00000    0.02892    0.03801 =
         0.02609   -0.00088    0.00661   -0.00013
C2    1    0.257015   -0.259635    0.072420    11.00000    0.03493    0.04063 =
         0.03434   -0.00623    0.00564   -0.00515
AFIX  43
H2    2    0.213559   -0.297193    0.035156    11.00000   -1.20000
AFIX   0
C3    1    0.313784   -0.343245    0.117023    11.00000    0.04009    0.03423 =
         0.04528    0.00034    0.01314   -0.00220
AFIX  43
H3    2    0.310927   -0.437699    0.109696    11.00000   -1.20000
AFIX   0
C4    1    0.375277   -0.287922    0.172852    11.00000    0.03275    0.04202 =
         0.03799    0.00901    0.01112    0.00312
C5    1    0.381142   -0.149952    0.182510    11.00000    0.03257    0.04415 =
         0.03200    0.00139    0.00216   -0.00400
AFIX  43
H5    2    0.423524   -0.112880    0.220824    11.00000   -1.20000
AFIX   0
C6    1    0.325221   -0.066484    0.136297    11.00000    0.03491    0.03408 =
         0.02962   -0.00157    0.00374   -0.00161
AFIX  43
H6    2    0.329795    0.028138    0.142281    11.00000   -1.20000
AFIX   0
C7    1    0.302919    0.117010   -0.003409    11.00000    0.03431    0.03666 =
         0.02905    0.00584    0.00374    0.00691
C8    1    0.350280    0.044065   -0.051478    11.00000    0.03929    0.03798 =
         0.02928    0.00219    0.00195    0.00916
AFIX  43
H8    2    0.324726   -0.033276   -0.076832    11.00000   -1.20000
AFIX   0
C9    1    0.434992    0.085036   -0.062108    11.00000    0.03928    0.05014 =
         0.03348    0.00579    0.00729    0.01435
AFIX  43
H9    2    0.467705    0.035373   -0.094846    11.00000   -1.20000
AFIX   0
C10   1    0.472400    0.197556   -0.025512    11.00000    0.03687    0.05214 =
         0.04154    0.01195    0.00619    0.00500
AFIX  43
H10   2    0.530653    0.225062   -0.032969    11.00000   -1.20000
AFIX   0
C11   1    0.424711    0.270034    0.022037    11.00000    0.04738    0.03939 =
         0.04322    0.00259    0.00412   -0.00186
AFIX  43
H11   2    0.450513    0.347237    0.047363    11.00000   -1.20000
AFIX   0
C12   1    0.339711    0.230938    0.032992    11.00000    0.04503    0.03786 =
         0.03725   -0.00068    0.00932    0.00473
AFIX  43
H12   2    0.306822    0.281627    0.065147    11.00000   -1.20000
AFIX   0
C13   1    0.191045   -0.038889    0.036016    11.00000    0.03201    0.04310 =
         0.02381   -0.00604    0.00290    0.00183
C14   1    0.142446    0.163910   -0.032680    11.00000    0.04091    0.04876 =
         0.04246   -0.00021   -0.00222    0.01412
AFIX 137
H14A  2    0.140816    0.153764   -0.087673    11.00000   -1.50000
H14B  2    0.154012    0.258020   -0.018666    11.00000   -1.50000
H14C  2    0.085162    0.136474   -0.017568    11.00000   -1.50000
AFIX   0
C15   1    0.432699   -0.379129    0.224451    11.00000    0.04969    0.05294 =
         0.05690    0.01687    0.00665    0.00832
 
PART -1
F1A'  5    0.273095   -0.020358    0.450699    31.00000    0.14814    0.07529 =
         0.04521    0.01993    0.01030    0.00491
F2A'  5    0.390711   -0.030664    0.402090    31.00000    0.05759    0.08552 =
         0.11470    0.03980   -0.03721   -0.00368
F3A'  5    0.289098   -0.177816    0.373114    31.00000    0.13461    0.02736 =
         0.09382    0.00938   -0.06512    0.00118
PART -2
F1B'  5    0.245997   -0.112409    0.420503   -31.00000    0.07489    0.06321 =
         0.05172    0.01452    0.00354    0.01344
F2B'  5    0.344887   -0.025895    0.442612   -31.00000    0.07489    0.06321 =
         0.05172    0.01452    0.00354    0.01344
F3B'  5    0.372857   -0.141127    0.356357   -31.00000    0.07489    0.06321 =
         0.05172    0.01452    0.00354    0.01344
PART 0
O1'   4    0.186137    0.377550    0.120143    11.00000    0.04481    0.03173 =
         0.04175    0.00327    0.01889   -0.00241
N1'   3    0.048768    0.309147    0.140150    11.00000    0.03454    0.03323 =
         0.02723    0.00580    0.00414    0.00104
C1'   1    0.180410    0.209552    0.213691    11.00000    0.02862    0.02655 =
         0.03006   -0.00343    0.00962    0.00061
C2'   1    0.253267    0.253115    0.262595    11.00000    0.03378    0.02709 =
         0.04125   -0.00415    0.00635   -0.00536
AFIX  43
H2'   2    0.275092    0.341755    0.258004    11.00000   -1.20000
AFIX   0
C3'   1    0.294399    0.168777    0.317932    11.00000    0.03328    0.03860 =
         0.03666   -0.00749   -0.00120   -0.00442
AFIX  43
H3'   2    0.343332    0.199823    0.352179    11.00000   -1.20000
AFIX   0
C4'   1    0.263683    0.038439    0.323084    11.00000    0.03232    0.03526 =
         0.03228   -0.00157    0.00265    0.00067
C5'   1    0.193146   -0.007678    0.272812    11.00000    0.03254    0.02658 =
         0.03854    0.00056    0.00450   -0.00251
AFIX  43
H5'   2    0.173569   -0.097902    0.275799    11.00000   -1.20000
AFIX   0
C6'   1    0.151123    0.077383    0.218238    11.00000    0.02886    0.02910 =
         0.03286   -0.00360    0.00209   -0.00172
AFIX  43
H6'   2    0.102401    0.045942    0.183893    11.00000   -1.20000
AFIX   0
C7'   1   -0.009608    0.250190    0.188490    11.00000    0.02731    0.02780 =
         0.03043    0.00358    0.00354    0.00366
C8'   1   -0.002352    0.284570    0.264585    11.00000    0.03024    0.02967 =
         0.03111   -0.00003    0.00249    0.00324
AFIX  43
H8'   2    0.041387    0.347395    0.285027    11.00000   -1.20000
AFIX   0
C9'   1   -0.059013    0.227109    0.310704    11.00000    0.04304    0.03773 =
         0.03547    0.00609    0.01195    0.00947
AFIX  43
H9'   2   -0.053451    0.249155    0.363084    11.00000   -1.20000
AFIX   0
C10'  1   -0.123626    0.137730    0.280545    11.00000    0.03915    0.03228 =
         0.05799    0.01150    0.01926    0.00526
AFIX  43
H10'  2   -0.162336    0.097942    0.312229    11.00000   -1.20000
AFIX   0
C11'  1   -0.131966    0.106201    0.204366    11.00000    0.03178    0.02969 =
         0.06379    0.00109    0.00393   -0.00156
AFIX  43
H11'  2   -0.177167    0.045810    0.183732    11.00000   -1.20000
AFIX   0
C12'  1   -0.075048    0.161772    0.157656    11.00000    0.03408    0.03338 =
         0.03712   -0.00165   -0.00112    0.00204
AFIX  43
H12'  2   -0.080793    0.139601    0.105287    11.00000   -1.20000
AFIX   0
C13'  1    0.138638    0.305944    0.154474    11.00000    0.03684    0.02443 =
         0.02828   -0.00317    0.00963   -0.00063
C14'  1    0.006874    0.393454    0.078139    11.00000    0.05057    0.04548 =
         0.03589    0.01410    0.00473    0.00725
AFIX 137
H14D  2    0.052975    0.435960    0.052287    11.00000   -1.50000
H14E  2   -0.029107    0.462945    0.098675    11.00000   -1.50000
H14F  2   -0.031269    0.337849    0.041978    11.00000   -1.50000
AFIX   0
C15'  1    0.304959   -0.051228    0.384452    11.00000    0.05318    0.05000 =
         0.04413    0.00795   -0.00995   -0.00586
 
HKLF   4
 
REM     NM03 in P 1 21/c 1
REM R1 =  0.0490 for   4629 Fo > 4sig(Fo)  and  0.0659 for all   6117 data
REM    395 parameters refined using      0 restraints
 
END  
     
WGHT      0.0639      0.7071 
REM Highest difference peak  0.381,  deepest hole -0.357,  1-sigma level  0.042
Q1    1   0.3955 -0.0977  0.3666  11.00000  0.05    0.38
Q2    1   0.4615 -0.2902  0.3001  11.00000  0.05    0.32
Q3    1   0.3419 -0.1821  0.3395  11.00000  0.05    0.29
Q4    1   0.4423 -0.5135  0.1869  11.00000  0.05    0.22
Q5    1   0.3598 -0.4411  0.2811  11.00000  0.05    0.22
;

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
F1A F 0.50289(16) -0.3232(2) 0.26051(18) 0.1014(11) Uani 0.850(5) 1 d P A -1
F2A F 0.38796(15) -0.4335(3) 0.27530(14) 0.1009(11) Uani 0.850(5) 1 d P A -1
F3A F 0.4606(3) -0.4839(3) 0.18729(15) 0.1395(16) Uani 0.850(5) 1 d P A -1
F1B F 0.5083(8) -0.3758(13) 0.2178(9) 0.074(3) Uani 0.150(5) 1 d P A -2
F2B F 0.4284(7) -0.3414(11) 0.3025(6) 0.074(3) Uani 0.150(5) 1 d P A -2
F3B F 0.4192(7) -0.4964(12) 0.2273(10) 0.074(3) Uani 0.150(5) 1 d P A -2
O1 O 0.11411(8) -0.07994(14) 0.02951(7) 0.0451(3) Uani 1 1 d . . .
N1 N 0.21326(9) 0.07937(14) 0.00601(8) 0.0357(3) Uani 1 1 d . . .
C1 C 0.26219(10) -0.12096(16) 0.08099(8) 0.0307(3) Uani 1 1 d . . .
C2 C 0.25701(11) -0.25964(17) 0.07242(10) 0.0365(4) Uani 1 1 d . . .
H2 H 0.2136 -0.2972 0.0352 0.044 Uiso 1 1 calc R . .
C3 C 0.31378(11) -0.34324(18) 0.11702(10) 0.0392(4) Uani 1 1 d . . .
H3 H 0.3109 -0.4377 0.1097 0.047 Uiso 1 1 calc R . .
C4 C 0.37528(11) -0.28792(17) 0.17285(10) 0.0370(4) Uani 1 1 d . A .
C5 C 0.38114(11) -0.14995(18) 0.18251(9) 0.0364(4) Uani 1 1 d . . .
H5 H 0.4235 -0.1129 0.2208 0.044 Uiso 1 1 calc R . .
C6 C 0.32522(11) -0.06648(17) 0.13630(9) 0.0329(4) Uani 1 1 d . . .
H6 H 0.3298 0.0281 0.1423 0.039 Uiso 1 1 calc R . .
C7 C 0.30292(11) 0.11701(17) -0.00341(9) 0.0334(4) Uani 1 1 d . . .
C8 C 0.35028(11) 0.04406(17) -0.05148(9) 0.0357(4) Uani 1 1 d . . .
H8 H 0.3247 -0.0333 -0.0768 0.043 Uiso 1 1 calc R . .
C9 C 0.43499(12) 0.08504(19) -0.06211(10) 0.0407(4) Uani 1 1 d . . .
H9 H 0.4677 0.0354 -0.0948 0.049 Uiso 1 1 calc R . .
C10 C 0.47240(12) 0.19756(19) -0.02551(10) 0.0434(4) Uani 1 1 d . . .
H10 H 0.5307 0.2251 -0.0330 0.052 Uiso 1 1 calc R . .
C11 C 0.42471(12) 0.27003(19) 0.02204(11) 0.0435(4) Uani 1 1 d . . .
H11 H 0.4505 0.3472 0.0474 0.052 Uiso 1 1 calc R . .
C12 C 0.33971(12) 0.23094(18) 0.03299(10) 0.0397(4) Uani 1 1 d . . .
H12 H 0.3068 0.2816 0.0651 0.048 Uiso 1 1 calc R . .
C13 C 0.19105(11) -0.03889(17) 0.03602(8) 0.0330(4) Uani 1 1 d . . .
C14 C 0.14245(12) 0.1639(2) -0.03268(10) 0.0447(4) Uani 1 1 d . . .
H14A H 0.1408 0.1538 -0.0877 0.067 Uiso 1 1 calc R . .
H14B H 0.1540 0.2580 -0.0187 0.067 Uiso 1 1 calc R . .
H14C H 0.0852 0.1365 -0.0176 0.067 Uiso 1 1 calc R . .
C15 C 0.43270(15) -0.3791(2) 0.22445(13) 0.0532(5) Uani 1 1 d . . .
F1A' F 0.27309(17) -0.0204(2) 0.45070(9) 0.0897(7) Uani 0.904(4) 1 d P B -1
F2A' F 0.39071(11) -0.03066(19) 0.40209(13) 0.0901(8) Uani 0.904(4) 1 d P B -1
F3A' F 0.28910(14) -0.17782(13) 0.37311(10) 0.0921(9) Uani 0.904(4) 1 d P B -1
F1B' F 0.2460(10) -0.1124(17) 0.4205(8) 0.064(4) Uani 0.096(4) 1 d P B -2
F2B' F 0.3449(14) -0.0259(15) 0.4426(9) 0.064(4) Uani 0.096(4) 1 d P B -2
F3B' F 0.3729(10) -0.1411(15) 0.3564(7) 0.064(4) Uani 0.096(4) 1 d P B -2
O1' O 0.18614(8) 0.37755(11) 0.12014(7) 0.0383(3) Uani 1 1 d . . .
N1' N 0.04877(9) 0.30915(13) 0.14015(7) 0.0316(3) Uani 1 1 d . . .
C1' C 0.18041(10) 0.20955(15) 0.21369(8) 0.0279(3) Uani 1 1 d . . .
C2' C 0.25327(11) 0.25311(16) 0.26260(9) 0.0339(4) Uani 1 1 d . . .
H2' H 0.2751 0.3418 0.2580 0.041 Uiso 1 1 calc R . .
C3' C 0.29440(11) 0.16878(17) 0.31793(10) 0.0367(4) Uani 1 1 d . . .
H3' H 0.3433 0.1998 0.3522 0.044 Uiso 1 1 calc R . .
C4' C 0.26368(11) 0.03844(16) 0.32308(9) 0.0334(4) Uani 1 1 d . B .
C5' C 0.19315(10) -0.00768(16) 0.27281(9) 0.0326(4) Uani 1 1 d . . .
H5' H 0.1736 -0.0979 0.2758 0.039 Uiso 1 1 calc R . .
C6' C 0.15112(10) 0.07738(15) 0.21824(9) 0.0304(3) Uani 1 1 d . . .
H6' H 0.1024 0.0459 0.1839 0.037 Uiso 1 1 calc R . .
C7' C -0.00961(10) 0.25019(15) 0.18849(9) 0.0285(3) Uani 1 1 d . . .
C8' C -0.00235(10) 0.28457(16) 0.26458(9) 0.0305(3) Uani 1 1 d . . .
H8' H 0.0414 0.3474 0.2850 0.037 Uiso 1 1 calc R . .
C9' C -0.05901(12) 0.22711(17) 0.31070(10) 0.0381(4) Uani 1 1 d . . .
H9' H -0.0535 0.2492 0.3631 0.046 Uiso 1 1 calc R . .
C10' C -0.12363(12) 0.13773(17) 0.28054(11) 0.0420(4) Uani 1 1 d . . .
H10' H -0.1623 0.0979 0.3122 0.050 Uiso 1 1 calc R . .
C11' C -0.13197(12) 0.10620(17) 0.20437(11) 0.0419(4) Uani 1 1 d . . .
H11' H -0.1772 0.0458 0.1837 0.050 Uiso 1 1 calc R . .
C12' C -0.07505(11) 0.16177(16) 0.15766(10) 0.0353(4) Uani 1 1 d . . .
H12' H -0.0808 0.1396 0.1053 0.042 Uiso 1 1 calc R . .
C13' C 0.13864(11) 0.30594(15) 0.15447(8) 0.0294(3) Uani 1 1 d . . .
C14' C 0.00687(13) 0.39345(19) 0.07814(10) 0.0440(4) Uani 1 1 d . . .
H14D H 0.0530 0.4360 0.0523 0.066 Uiso 1 1 calc R . .
H14E H -0.0291 0.4629 0.0987 0.066 Uiso 1 1 calc R . .
H14F H -0.0313 0.3378 0.0420 0.066 Uiso 1 1 calc R . .
C15' C 0.30496(14) -0.0512(2) 0.38445(12) 0.0505(5) 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
F1A C15 1.297(3) . ?
F2A C15 1.314(3) . ?
F3A C15 1.333(3) . ?
F1B C15 1.168(12) . ?
F2B C15 1.447(12) . ?
F3B C15 1.188(11) . ?
O1 C13 1.228(2) . ?
N1 C13 1.353(2) . ?
N1 C7 1.440(2) . ?
N1 C14 1.466(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.392(2) . ?
C1 C13 1.501(2) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 C15 1.491(3) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.388(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
F1A' C15' 1.363(3) . ?
F2A' C15' 1.314(3) . ?
F3A' C15' 1.295(2) . ?
F1B' C15' 1.314(15) . ?
F1B' F2B' 1.73(3) . ?
F2B' C15' 1.158(15) . ?
F3B' C15' 1.497(14) . ?
O1' C13' 1.2293(18) . ?
N1' C13' 1.355(2) . ?
N1' C7' 1.435(2) . ?
N1' C14' 1.465(2) . ?
C1' C2' 1.386(2) . ?
C1' C6' 1.395(2) . ?
C1' C13' 1.504(2) . ?
C2' C3' 1.381(2) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.386(2) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.383(2) . ?
C4' C15' 1.485(2) . ?
C5' C6' 1.382(2) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C8' 1.386(2) . ?
C7' C12' 1.387(2) . ?
C8' C9' 1.384(2) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.381(3) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.380(3) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.386(2) . ?
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 123.93(13) . . ?
C13 N1 C14 118.75(14) . . ?
C7 N1 C14 116.25(14) . . ?
C2 C1 C6 119.26(15) . . ?
C2 C1 C13 117.11(14) . . ?
C6 C1 C13 123.16(15) . . ?
C3 C2 C1 121.05(16) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.15(16) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.61(16) . . ?
C5 C4 C15 120.30(17) . . ?
C3 C4 C15 119.05(17) . . ?
C6 C5 C4 119.86(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.03(15) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C12 C7 C8 120.39(16) . . ?
C12 C7 N1 119.23(14) . . ?
C8 C7 N1 120.30(15) . . ?
C9 C8 C7 119.41(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.54(16) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.74(17) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.50(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 119.42(16) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
O1 C13 N1 122.26(15) . . ?
O1 C13 C1 118.63(15) . . ?
N1 C13 C1 119.08(14) . . ?
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 . . ?
F1B C15 F3B 102.0(8) . . ?
F3B C15 F1A 122.4(5) . . ?
F1B C15 F2A 132.9(6) . . ?
F1A C15 F2A 107.5(2) . . ?
F1A C15 F3A 106.8(3) . . ?
F2A C15 F3A 104.0(3) . . ?
F1B C15 F2B 104.7(9) . . ?
F3B C15 F2B 100.7(9) . . ?
F3A C15 F2B 137.3(4) . . ?
F1B C15 C4 115.1(5) . . ?
F3B C15 C4 122.4(6) . . ?
F1A C15 C4 114.93(19) . . ?
F2A C15 C4 111.24(19) . . ?
F3A C15 C4 111.70(19) . . ?
F2B C15 C4 109.8(4) . . ?
C13' N1' C7' 124.05(13) . . ?
C13' N1' C14' 119.01(13) . . ?
C7' N1' C14' 116.33(13) . . ?
C2' C1' C6' 119.56(15) . . ?
C2' C1' C13' 118.08(13) . . ?
C6' C1' C13' 122.28(14) . . ?
C3' C2' C1' 120.57(14) . . ?
C3' C2' H2' 119.7 . . ?
C1' C2' H2' 119.7 . . ?
C2' C3' C4' 119.44(15) . . ?
C2' C3' H3' 120.3 . . ?
C4' C3' H3' 120.3 . . ?
C5' C4' C3' 120.49(15) . . ?
C5' C4' C15' 119.64(15) . . ?
C3' C4' C15' 119.85(15) . . ?
C6' C5' C4' 120.03(14) . . ?
C6' C5' H5' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C5' C6' C1' 119.84(15) . . ?
C5' C6' H6' 120.1 . . ?
C1' C6' H6' 120.1 . . ?
C8' C7' C12' 120.47(14) . . ?
C8' C7' N1' 120.30(14) . . ?
C12' C7' N1' 119.20(14) . . ?
C9' C8' C7' 119.82(15) . . ?
C9' C8' H8' 120.1 . . ?
C7' C8' H8' 120.1 . . ?
C10' C9' C8' 119.98(16) . . ?
C10' C9' H9' 120.0 . . ?
C8' C9' H9' 120.0 . . ?
C11' C10' C9' 120.00(16) . . ?
C11' C10' H10' 120.0 . . ?
C9' C10' H10' 120.0 . . ?
C10' C11' C12' 120.67(16) . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' H11' 119.7 . . ?
C11' C12' C7' 119.04(16) . . ?
C11' C12' H12' 120.5 . . ?
C7' C12' H12' 120.5 . . ?
O1' C13' N1' 122.12(15) . . ?
O1' C13' C1' 119.77(14) . . ?
N1' C13' C1' 118.11(13) . . ?
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 . . ?
F2B' C15' F3A' 114.7(8) . . ?
F2B' C15' F1B' 88.7(12) . . ?
F3A' C15' F2A' 110.3(2) . . ?
F1B' C15' F2A' 132.0(6) . . ?
F3A' C15' F1A' 105.96(19) . . ?
F2A' C15' F1A' 101.9(2) . . ?
F2B' C15' C4' 130.5(7) . . ?
F3A' C15' C4' 114.74(16) . . ?
F1B' C15' C4' 112.8(6) . . ?
F2A' C15' C4' 113.18(17) . . ?
F1A' C15' C4' 109.65(18) . . ?
F2B' C15' F3B' 97.1(11) . . ?
F1B' C15' F3B' 115.1(9) . . ?
F1A' C15' F3B' 139.2(5) . . ?
C4' C15' F3B' 111.0(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
C6 C1 C2 C3 -0.8(2) . . . . ?
C13 C1 C2 C3 -173.25(15) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C2 C3 C4 C15 176.02(16) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C15 C4 C5 C6 -177.47(16) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C13 C1 C6 C5 171.27(14) . . . . ?
C13 N1 C7 C12 -119.88(17) . . . . ?
C14 N1 C7 C12 72.18(19) . . . . ?
C13 N1 C7 C8 63.4(2) . . . . ?
C14 N1 C7 C8 -104.50(18) . . . . ?
C12 C7 C8 C9 0.8(2) . . . . ?
N1 C7 C8 C9 177.41(14) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C7 0.9(3) . . . . ?
C8 C7 C12 C11 -1.1(2) . . . . ?
N1 C7 C12 C11 -177.80(15) . . . . ?
C7 N1 C13 O1 -164.90(15) . . . . ?
C14 N1 C13 O1 2.7(2) . . . . ?
C7 N1 C13 C1 17.1(2) . . . . ?
C14 N1 C13 C1 -175.24(14) . . . . ?
C2 C1 C13 O1 39.9(2) . . . . ?
C6 C1 C13 O1 -132.21(17) . . . . ?
C2 C1 C13 N1 -142.04(15) . . . . ?
C6 C1 C13 N1 45.8(2) . . . . ?
C5 C4 C15 F1B -69.2(10) . . . . ?
C3 C4 C15 F1B 113.2(10) . . . . ?
C5 C4 C15 F3B 166.1(11) . . . . ?
C3 C4 C15 F3B -11.5(12) . . . . ?
C5 C4 C15 F1A -20.1(3) . . . . ?
C3 C4 C15 F1A 162.3(3) . . . . ?
C5 C4 C15 F2A 102.3(3) . . . . ?
C3 C4 C15 F2A -75.3(3) . . . . ?
C5 C4 C15 F3A -141.9(3) . . . . ?
C3 C4 C15 F3A 40.4(3) . . . . ?
C5 C4 C15 F2B 48.6(5) . . . . ?
C3 C4 C15 F2B -129.0(5) . . . . ?
C6' C1' C2' C3' -3.0(2) . . . . ?
C13' C1' C2' C3' -179.84(14) . . . . ?
C1' C2' C3' C4' 1.7(2) . . . . ?
C2' C3' C4' C5' 0.8(3) . . . . ?
C2' C3' C4' C15' -177.39(17) . . . . ?
C3' C4' C5' C6' -1.8(2) . . . . ?
C15' C4' C5' C6' 176.35(16) . . . . ?
C4' C5' C6' C1' 0.4(2) . . . . ?
C2' C1' C6' C5' 2.0(2) . . . . ?
C13' C1' C6' C5' 178.65(14) . . . . ?
C13' N1' C7' C8' 54.7(2) . . . . ?
C14' N1' C7' C8' -116.25(16) . . . . ?
C13' N1' C7' C12' -127.34(16) . . . . ?
C14' N1' C7' C12' 61.75(19) . . . . ?
C12' C7' C8' C9' 2.0(2) . . . . ?
N1' C7' C8' C9' 179.99(14) . . . . ?
C7' C8' C9' C10' -1.2(2) . . . . ?
C8' C9' C10' C11' -0.3(2) . . . . ?
C9' C10' C11' C12' 1.0(3) . . . . ?
C10' C11' C12' C7' -0.3(2) . . . . ?
C8' C7' C12' C11' -1.3(2) . . . . ?
N1' C7' C12' C11' -179.27(14) . . . . ?
C7' N1' C13' O1' -166.23(14) . . . . ?
C14' N1' C13' O1' 4.5(2) . . . . ?
C7' N1' C13' C1' 14.7(2) . . . . ?
C14' N1' C13' C1' -174.64(14) . . . . ?
C2' C1' C13' O1' 41.4(2) . . . . ?
C6' C1' C13' O1' -135.34(16) . . . . ?
C2' C1' C13' N1' -139.49(15) . . . . ?
C6' C1' C13' N1' 43.8(2) . . . . ?
F1B' F2B' C15' F3A' -55.9(9) . . . . ?
F1B' F2B' C15' F2A' -152.6(9) . . . . ?
F1B' F2B' C15' F1A' 35.5(9) . . . . ?
F1B' F2B' C15' C4' 119.3(11) . . . . ?
F1B' F2B' C15' F3B' -115.1(9) . . . . ?
F2B' F1B' C15' F3A' 119.7(9) . . . . ?
F2B' F1B' C15' F2A' 28.6(11) . . . . ?
F2B' F1B' C15' F1A' -37.1(9) . . . . ?
F2B' F1B' C15' C4' -134.0(9) . . . . ?
F2B' F1B' C15' F3B' 97.3(11) . . . . ?
C5' C4' C15' F2B' -155.7(15) . . . . ?
C3' C4' C15' F2B' 22.4(15) . . . . ?
C5' C4' C15' F3A' 19.4(3) . . . . ?
C3' C4' C15' F3A' -162.4(2) . . . . ?
C5' C4' C15' F1B' -46.8(9) . . . . ?
C3' C4' C15' F1B' 131.4(9) . . . . ?
C5' C4' C15' F2A' 147.3(2) . . . . ?
C3' C4' C15' F2A' -34.6(3) . . . . ?
C5' C4' C15' F1A' -99.6(2) . . . . ?
C3' C4' C15' F1A' 78.5(2) . . . . ?
C5' C4' C15' F3B' 84.1(7) . . . . ?
C3' C4' C15' F3B' -97.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_NM10
_database_code_depnum_ccdc_archive 'CCDC 1025679'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 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           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

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

_cell_length_a                   9.6555(7)
_cell_length_b                   13.7420(11)
_cell_length_c                   19.3339(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2565.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3989
_cell_measurement_theta_min      2.3530
_cell_measurement_theta_max      29.3046

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9237
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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            12605
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2262
_reflns_number_gt                1743
_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          
; 
 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. 
;

_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)+(0.0425P)²+0.5802P] 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     SHELXL
_refine_ls_extinction_coef       0.0077(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2262
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    NM10 in P b c a
CELL   0.71073   9.6555  13.7420  19.3339  90.000  90.000  90.000
ZERR     8       0.0007   0.0011   0.0015   0.000   0.000   0.000
LATT  1
SYMM  0.50000-X,-Y, 0.50000+Z
SYMM  0.50000+X, 0.50000-Y,-Z
SYMM -X, 0.50000+Y, 0.50000-Z
SFAC    C   H   N   O   F
UNIT   120 96   8   8  24
MERG    2
L.S.    12
OMIT -1 50
ACTA
BOND $H
HTAB
CONF
SIZE 0.3 0.22 0.2
TEMP -153
FMAP    2
PLAN    5
WGHT    0.042500    0.580200
EXTI    0.007696
FVAR       3.07145   0.53962
part 1
F1A   5    0.441263    0.227555    0.440296    21.00000    0.04005    0.09926 =
         0.03905    0.03605   -0.00247    0.01950
F2A   5    0.593393    0.172075    0.514219    21.00000    0.01947    0.04523 =
         0.03664    0.00263    0.00244    0.01008
F3A   5    0.476997    0.296423    0.542112    21.00000    0.05704    0.02568 =
         0.05352    0.00214    0.02392   -0.00431
part 2
F1B   5    0.435140    0.222620    0.441090   -21.00000    0.06174    0.10028 =
         0.02485    0.02817    0.00613   -0.03676
F2B   5    0.572424    0.184578    0.514904   -21.00000    0.01346    0.09080 =
         0.07133    0.04928    0.00447    0.00546
F3B   5    0.437296    0.305499    0.526640   -21.00000    0.10645    0.02511 =
         0.09053    0.00367    0.07207    0.00165
part 0
 
N1    3    0.334110    0.232306    0.651805    11.00000    0.01835    0.02604 =
         0.02552   -0.00371   -0.00123    0.00338
O1    4    0.497221    0.320049    0.707240    11.00000    0.03065    0.03085 =
         0.05802   -0.01745   -0.00916    0.00277
C1    1    0.564000    0.160393    0.676043    11.00000    0.02274    0.02760 =
         0.01683   -0.00236   -0.00312    0.00133
C2    1    0.702933    0.183681    0.667404    11.00000    0.02136    0.02949 =
         0.02830    0.00046   -0.00219   -0.00333
AFIX  43
H2    2    0.729621    0.249508    0.660503    11.00000   -1.20000
AFIX   0
C3    1    0.802608    0.111331    0.668815    11.00000    0.02011    0.04246 =
         0.02976   -0.00158   -0.00116    0.00418
AFIX  43
H3    2    0.897206    0.127619    0.661853    11.00000   -1.20000
AFIX   0
C4    1    0.765374    0.015295    0.680312    11.00000    0.02887    0.03444 =
         0.02311   -0.00218   -0.00367    0.01051
AFIX  43
H4    2    0.834081   -0.034159    0.681528    11.00000   -1.20000
AFIX   0
C5    1    0.626791   -0.008067    0.690044    11.00000    0.03180    0.02480 =
         0.02244    0.00127   -0.00251    0.00286
AFIX  43
H5    2    0.600604   -0.073653    0.698426    11.00000   -1.20000
AFIX   0
C6    1    0.526619    0.064077    0.687556    11.00000    0.02146    0.02910 =
         0.01903   -0.00019   -0.00037   -0.00173
AFIX  43
H6    2    0.431873    0.047604    0.693755    11.00000   -1.20000
AFIX   0
C7    1    0.294116    0.156292    0.605026    11.00000    0.01784    0.02395 =
         0.02246    0.00118   -0.00372    0.00451
C8    1    0.190096    0.093051    0.626238    11.00000    0.02078    0.03088 =
         0.02593    0.00075    0.00061    0.00129
AFIX  43
H8    2    0.151506    0.100069    0.671161    11.00000   -1.20000
AFIX   0
C9    1    0.141688    0.020229    0.583357    11.00000    0.02298    0.03070 =
         0.04356   -0.00075   -0.00481   -0.00050
AFIX  43
H9    2    0.069771   -0.021864    0.598500    11.00000   -1.20000
AFIX   0
C10   1    0.198563    0.009039    0.518319    11.00000    0.03407    0.03151 =
         0.04225   -0.01147   -0.01177    0.00369
AFIX  43
H10   2    0.167065   -0.041579    0.488780    11.00000   -1.20000
AFIX   0
C11   1    0.300816    0.071326    0.496477    11.00000    0.03617    0.03954 =
         0.02450   -0.00460   -0.00057    0.01059
AFIX  43
H11   2    0.339931    0.062895    0.451791    11.00000   -1.20000
AFIX   0
C12   1    0.348433    0.146675    0.538501    11.00000    0.02573    0.02663 =
         0.02218    0.00225   -0.00063    0.00723
C13   1    0.462748    0.243473    0.678793    11.00000    0.02286    0.02613 =
         0.02595   -0.00142    0.00013    0.00093
C14   1    0.230198    0.308838    0.662346    11.00000    0.02626    0.02953 =
         0.03290   -0.00495   -0.00257    0.00839
AFIX 137
H14A  2    0.265679    0.356777    0.695426    11.00000   -1.50000
H14B  2    0.144868    0.279869    0.680493    11.00000   -1.50000
H14C  2    0.210667    0.340969    0.618158    11.00000   -1.50000
AFIX   0
C15   1    0.456805    0.212305    0.508433    11.00000    0.03648    0.03378 =
         0.02638    0.00321    0.00955    0.00806
HKLF   4
 
REM     NM10 in P b c a
REM R1 =  0.0398 for   1743 Fo > 4sig(Fo)  and  0.0580 for all   2262 data
REM    211 parameters refined using      0 restraints
 
END  
     
WGHT      0.0425      0.5802 
REM Highest difference peak  0.207,  deepest hole -0.221,  1-sigma level  0.050
Q1    1   0.6272  0.1687  0.6535  11.00000  0.05    0.21
Q2    1   0.2706  0.3817  0.6613  11.00000  0.05    0.19
Q3    1   0.5232  0.4051  0.6657  11.00000  0.05    0.19
Q4    1   0.5237  0.1955  0.6655  11.00000  0.05    0.19
Q5    1   0.3459  0.0950  0.5257  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
F1A F 0.4413(10) 0.2276(9) 0.4403(6) 0.059(4) Uani 0.54(6) 1 d P A 1
F2A F 0.5934(15) 0.1721(9) 0.5142(5) 0.034(2) Uani 0.54(6) 1 d P A 1
F3A F 0.4770(14) 0.2964(11) 0.5421(7) 0.045(2) Uani 0.54(6) 1 d P A 1
F1B F 0.4351(12) 0.2226(10) 0.4411(7) 0.062(4) Uani 0.46(6) 1 d P A 2
F2B F 0.572(2) 0.1846(16) 0.5149(7) 0.059(4) Uani 0.46(6) 1 d P A 2
F3B F 0.437(5) 0.3055(12) 0.5266(19) 0.074(6) Uani 0.46(6) 1 d P A 2
N1 N 0.33411(15) 0.23231(11) 0.65181(8) 0.0233(4) Uani 1 1 d . . .
O1 O 0.49722(14) 0.32005(10) 0.70724(8) 0.0398(4) Uani 1 1 d . . .
C1 C 0.56400(18) 0.16039(13) 0.67604(9) 0.0224(4) Uani 1 1 d . . .
C2 C 0.70293(18) 0.18368(14) 0.66740(10) 0.0264(5) Uani 1 1 d . . .
H2 H 0.7296 0.2495 0.6605 0.032 Uiso 1 1 calc R . .
C3 C 0.8026(2) 0.11133(15) 0.66881(10) 0.0308(5) Uani 1 1 d . . .
H3 H 0.8972 0.1276 0.6619 0.037 Uiso 1 1 calc R . .
C4 C 0.7654(2) 0.01529(14) 0.68031(9) 0.0288(5) Uani 1 1 d . . .
H4 H 0.8341 -0.0342 0.6815 0.035 Uiso 1 1 calc R . .
C5 C 0.6268(2) -0.00807(14) 0.69004(9) 0.0263(5) Uani 1 1 d . . .
H5 H 0.6006 -0.0737 0.6984 0.032 Uiso 1 1 calc R . .
C6 C 0.52662(19) 0.06408(13) 0.68756(9) 0.0232(4) Uani 1 1 d . . .
H6 H 0.4319 0.0476 0.6938 0.028 Uiso 1 1 calc R . .
C7 C 0.29412(17) 0.15629(13) 0.60503(9) 0.0214(4) Uani 1 1 d . . .
C8 C 0.19010(18) 0.09305(13) 0.62624(10) 0.0259(5) Uani 1 1 d . . .
H8 H 0.1515 0.1001 0.6712 0.031 Uiso 1 1 calc R . .
C9 C 0.1417(2) 0.02023(14) 0.58336(10) 0.0324(5) Uani 1 1 d . . .
H9 H 0.0698 -0.0219 0.5985 0.039 Uiso 1 1 calc R . .
C10 C 0.1986(2) 0.00904(15) 0.51832(11) 0.0359(5) Uani 1 1 d . . .
H10 H 0.1671 -0.0416 0.4888 0.043 Uiso 1 1 calc R . .
C11 C 0.3008(2) 0.07133(15) 0.49648(10) 0.0334(5) Uani 1 1 d . . .
H11 H 0.3399 0.0629 0.4518 0.040 Uiso 1 1 calc R . .
C12 C 0.34843(18) 0.14667(13) 0.53850(9) 0.0249(4) Uani 1 1 d . A .
C13 C 0.46275(18) 0.24347(13) 0.67879(10) 0.0250(5) Uani 1 1 d . . .
C14 C 0.2302(2) 0.30884(13) 0.66235(10) 0.0296(5) Uani 1 1 d . . .
H14A H 0.2657 0.3568 0.6954 0.044 Uiso 1 1 calc R . .
H14B H 0.1449 0.2799 0.6805 0.044 Uiso 1 1 calc R . .
H14C H 0.2107 0.3410 0.6182 0.044 Uiso 1 1 calc R . .
C15 C 0.4568(2) 0.21230(15) 0.50843(11) 0.0322(5) 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
F1A C15 1.342(11) . ?
F2A C15 1.434(16) . ?
F3A C15 1.341(14) . ?
F1B C15 1.326(13) . ?
F2B C15 1.19(3) . ?
F3B C15 1.341(16) . ?
N1 C13 1.356(2) . ?
N1 C7 1.435(2) . ?
N1 C14 1.468(2) . ?
O1 C13 1.233(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.390(3) . ?
C1 C13 1.504(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 C12 1.395(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C15 1.499(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 124.86(15) . . ?
C13 N1 C14 119.45(15) . . ?
C7 N1 C14 115.17(14) . . ?
C2 C1 C6 119.30(17) . . ?
C2 C1 C13 117.20(16) . . ?
C6 C1 C13 123.26(16) . . ?
C3 C2 C1 120.24(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.46(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.46(18) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.15(18) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.37(17) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C12 118.97(17) . . ?
C8 C7 N1 117.63(16) . . ?
C12 C7 N1 123.29(16) . . ?
C9 C8 C7 121.36(18) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.53(19) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 119.78(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.39(19) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 118.92(17) . . ?
C11 C12 C15 116.82(17) . . ?
C7 C12 C15 124.26(17) . . ?
O1 C13 N1 121.03(16) . . ?
O1 C13 C1 119.22(16) . . ?
N1 C13 C1 119.73(16) . . ?
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 . . ?
F2B C15 F1B 106.6(9) . . ?
F2B C15 F3A 95.1(7) . . ?
F1B C15 F3A 114.0(8) . . ?
F2B C15 F3B 114.3(17) . . ?
F1B C15 F3B 97.7(19) . . ?
F2B C15 F1A 105.0(8) . . ?
F3A C15 F1A 111.0(7) . . ?
F3B C15 F1A 95.3(17) . . ?
F1B C15 F2A 105.2(7) . . ?
F3A C15 F2A 99.2(7) . . ?
F3B C15 F2A 118(2) . . ?
F1A C15 F2A 103.9(6) . . ?
F2B C15 C12 115.0(8) . . ?
F1B C15 C12 109.6(6) . . ?
F3A C15 C12 115.6(6) . . ?
F3B C15 C12 112.0(9) . . ?
F1A C15 C12 113.4(6) . . ?
F2A C15 C12 112.3(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
C6 C1 C2 C3 1.4(3) . . . . ?
C13 C1 C2 C3 175.90(17) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C13 C1 C6 C5 -174.53(16) . . . . ?
C13 N1 C7 C8 119.14(19) . . . . ?
C14 N1 C7 C8 -69.3(2) . . . . ?
C13 N1 C7 C12 -64.7(2) . . . . ?
C14 N1 C7 C12 106.86(19) . . . . ?
C12 C7 C8 C9 1.2(3) . . . . ?
N1 C7 C8 C9 177.48(16) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C7 2.4(3) . . . . ?
C10 C11 C12 C15 -177.93(18) . . . . ?
C8 C7 C12 C11 -2.7(3) . . . . ?
N1 C7 C12 C11 -178.77(16) . . . . ?
C8 C7 C12 C15 177.63(17) . . . . ?
N1 C7 C12 C15 1.6(3) . . . . ?
C7 N1 C13 O1 165.43(18) . . . . ?
C14 N1 C13 O1 -5.8(3) . . . . ?
C7 N1 C13 C1 -16.4(3) . . . . ?
C14 N1 C13 C1 172.30(16) . . . . ?
C2 C1 C13 O1 -36.2(3) . . . . ?
C6 C1 C13 O1 138.15(19) . . . . ?
C2 C1 C13 N1 145.65(18) . . . . ?
C6 C1 C13 N1 -40.0(3) . . . . ?
C11 C12 C15 F2B -85.9(9) . . . . ?
C7 C12 C15 F2B 93.7(9) . . . . ?
C11 C12 C15 F1B 34.2(6) . . . . ?
C7 C12 C15 F1B -146.2(6) . . . . ?
C11 C12 C15 F3A 164.7(7) . . . . ?
C7 C12 C15 F3A -15.7(8) . . . . ?
C11 C12 C15 F3B 141(3) . . . . ?
C7 C12 C15 F3B -39(3) . . . . ?
C11 C12 C15 F1A 34.9(5) . . . . ?
C7 C12 C15 F1A -145.4(5) . . . . ?
C11 C12 C15 F2A -82.4(4) . . . . ?
C7 C12 C15 F2A 97.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_NM11
_database_code_depnum_ccdc_archive 'CCDC 1025680'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N O'
_chemical_formula_sum            'C16 H11 F6 N O'
_chemical_formula_weight         347.26

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                   8.9803(4)
_cell_length_b                   10.8526(4)
_cell_length_c                   14.8181(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.763(3)
_cell_angle_gamma                90.00
_cell_volume                     1442.49(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7726
_cell_measurement_theta_min      2.5926
_cell_measurement_theta_max      29.3278

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9213
_exptl_absorpt_correction_T_max  0.9530
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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            13687
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2534
_reflns_number_gt                2204
_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          
; 
 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. 
;

_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)+(0.0436P)²+0.8475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    NM11 in P 1 21/c 1
CELL   0.71073   8.9803  10.8526  14.8181  90.000  92.763  90.000
ZERR     4       0.10004   0.0004   0.0005   0.000   0.003   0.000
LATT  1
SYMM -X, 0.50000+Y, 0.50000-Z
SFAC    C   H   N   O   F
UNIT    64  44   4   4  24
MERG    2
L.S.    12
OMIT -1 50
acta
htab
conf
bond $h
EADP N1A N1B
EADP C13A C13B
temp -153
SIZE 0.4 0.3 0.18
FMAP    2
PLAN    5
WGHT    0.043600    0.847500
FVAR       5.54857   0.93859
PART 1
N1A   3    0.633059    0.275317    0.870615    21.00000    0.01707    0.02345 =
         0.02545   -0.00102    0.00028    0.00047
C13A  1    0.765142    0.215112    0.869127    21.00000    0.02034    0.02684 =
         0.01479   -0.00061    0.00141    0.00266
PART 2
N1B   3    0.720042    0.298586    0.885714   -21.00000    0.01707    0.02345 =
         0.02545   -0.00102    0.00028    0.00047
C13B  1    0.674724    0.183903    0.862021   -21.00000    0.02034    0.02684 =
         0.01479   -0.00061    0.00141    0.00266
PART 0
O1    4    0.773987    0.102697    0.864130    11.00000    0.02540    0.02315 =
         0.04119   -0.00241    0.00734    0.00277
F1    5    0.356684    0.205310    0.637679    11.00000    0.03748    0.06266 =
         0.02247    0.00871   -0.00828   -0.01570
F2    5    0.468026    0.356152    0.704574    11.00000    0.05989    0.03272 =
         0.03574    0.00841    0.00670   -0.00998
F3    5    0.585244    0.188510    0.681370    11.00000    0.03221    0.06209 =
         0.02800    0.00567    0.01204    0.00530
F4    5    0.822141    0.274944    1.049971    11.00000    0.02184    0.07872 =
         0.02642    0.00701    0.00411    0.00232
F5    5    1.042085    0.321786    1.098698    11.00000    0.03656    0.07009 =
         0.02442   -0.00169   -0.00967   -0.00668
F6    5    0.999690    0.145339    1.039115    11.00000    0.06116    0.03970 =
         0.04007    0.01279    0.01883    0.00590
C1    1    0.901925    0.295716    0.865682    11.00000    0.01765    0.03174 =
         0.02407    0.00157    0.00179   -0.00123
C2    1    0.998315    0.316984    0.940874    11.00000    0.01989    0.02547 =
         0.02497    0.00027    0.00006    0.00221
C3    1    1.128782    0.383517    0.931031    11.00000    0.01611    0.02975 =
         0.03390   -0.00412   -0.00196    0.00065
AFIX  43
H3    2    1.195520    0.396790    0.981803    11.00000   -1.20000
AFIX   0
C4    1    1.161726    0.430431    0.847597    11.00000    0.01869    0.02719 =
         0.04532    0.00090    0.00759   -0.00232
AFIX  43
H4    2    1.250688    0.476402    0.841444    11.00000   -1.20000
AFIX   0
C5    1    1.066159    0.410928    0.773076    11.00000    0.02495    0.03365 =
         0.03255    0.00931    0.00775    0.00111
AFIX  43
H5    2    1.088918    0.443624    0.715888    11.00000   -1.20000
AFIX   0
C6    1    0.937298    0.343550    0.782333    11.00000    0.02362    0.03988 =
         0.02491    0.00385   -0.00088   -0.00278
AFIX  43
H6    2    0.871904    0.329691    0.731024    11.00000   -1.20000
AFIX   0
C7    1    0.499062    0.201352    0.872518    11.00000    0.01492    0.03016 =
         0.02478    0.00074    0.00122   -0.00046
C8    1    0.456644    0.152848    0.953872    11.00000    0.02103    0.03925 =
         0.02125    0.00076   -0.00062    0.00253
AFIX  43
H8    2    0.519133    0.163429    1.006877    11.00000   -1.20000
AFIX   0
C9    1    0.323550    0.088975    0.958354    11.00000    0.02649    0.02893 =
         0.02510    0.00531    0.00812    0.00284
AFIX  43
H9    2    0.295425    0.054949    1.014095    11.00000   -1.20000
AFIX   0
C10   1    0.231906    0.074988    0.881379    11.00000    0.02272    0.02570 =
         0.03156   -0.00154    0.00645   -0.00494
AFIX  43
H10   2    0.139522    0.032970    0.884667    11.00000   -1.20000
AFIX   0
C11   1    0.274007    0.121906    0.799430    11.00000    0.01981    0.02574 =
         0.02618   -0.00339   -0.00084   -0.00293
AFIX  43
H11   2    0.210755    0.111480    0.746731    11.00000   -1.20000
AFIX   0
C12   1    0.408313    0.184062    0.794193    11.00000    0.01909    0.02438 =
         0.02171    0.00063    0.00125    0.00034
C14   1    0.618883    0.404989    0.895505    11.00000    0.01855    0.02245 =
         0.04247   -0.00690    0.00046    0.00194
C15   1    0.454103    0.233448    0.705436    11.00000    0.02069    0.03309 =
         0.02463    0.00088   -0.00075   -0.00405
C16   1    0.965543    0.265114    1.031262    11.00000    0.02037    0.03882 =
         0.02369   -0.00136   -0.00202    0.00035
 
H14A  2    0.709665    0.448220    0.887950    11.00000    0.04991
H14B  2    0.595255    0.408994    0.955256    11.00000    0.04870
H14C  2    0.540178    0.439918    0.860471    11.00000    0.04718
HKLF   4
 
REM     NM11 in P 1 21/c 1
REM R1 =  0.0368 for   2204 Fo > 4sig(Fo)  and  0.0434 for all   2534 data
REM    236 parameters refined using      0 restraints
 
END  
     
WGHT      0.0436      0.8475 
REM Highest difference peak  0.308,  deepest hole -0.237,  1-sigma level  0.042
Q1    1   0.8986  0.1586  1.0262  11.00000  0.05    0.31
Q2    1   0.8616  0.3564  0.8720  11.00000  0.05    0.28
Q3    1   0.7710  0.1278  0.8065  11.00000  0.05    0.26
Q4    1   0.3192  0.2814  0.6596  11.00000  0.05    0.25
Q5    1   0.5228  0.1328  0.8664  11.00000  0.05    0.24 
;

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
N1A N 0.63306(19) 0.27532(14) 0.87062(10) 0.0220(4) Uani 0.939(3) 1 d P A 1
C13A C 0.7651(2) 0.21511(17) 0.86913(11) 0.0206(4) Uani 0.939(3) 1 d P A 1
N1B N 0.720(3) 0.299(2) 0.8857(16) 0.0220(4) Uani 0.061(3) 1 d P A 2
C13B C 0.675(4) 0.184(3) 0.8620(17) 0.0206(4) Uani 0.061(3) 1 d P A 2
O1 O 0.77399(13) 0.10270(11) 0.86413(8) 0.0297(3) Uani 1 1 d . . .
F1 F 0.35668(12) 0.20531(12) 0.63768(7) 0.0412(3) Uani 1 1 d . A .
F2 F 0.46803(14) 0.35615(10) 0.70457(7) 0.0426(3) Uani 1 1 d . A .
F3 F 0.58524(12) 0.18851(11) 0.68137(7) 0.0404(3) Uani 1 1 d . A .
F4 F 0.82214(11) 0.27494(12) 1.04997(7) 0.0422(3) Uani 1 1 d . A .
F5 F 1.04208(12) 0.32179(12) 1.09870(7) 0.0440(3) Uani 1 1 d . A .
F6 F 0.99969(14) 0.14534(11) 1.03911(8) 0.0464(3) Uani 1 1 d . A .
C1 C 0.90192(18) 0.29572(16) 0.86568(11) 0.0245(4) Uani 1 1 d . . .
C2 C 0.99831(18) 0.31698(15) 0.94087(11) 0.0235(4) Uani 1 1 d . A .
C3 C 1.12878(18) 0.38352(16) 0.93103(12) 0.0267(4) Uani 1 1 d . . .
H3 H 1.1955 0.3968 0.9818 0.032 Uiso 1 1 calc R A .
C4 C 1.16173(19) 0.43043(16) 0.84760(13) 0.0302(4) Uani 1 1 d . A .
H4 H 1.2507 0.4764 0.8414 0.036 Uiso 1 1 calc R . .
C5 C 1.0662(2) 0.41093(17) 0.77308(13) 0.0302(4) Uani 1 1 d . . .
H5 H 1.0889 0.4436 0.7159 0.036 Uiso 1 1 calc R A .
C6 C 0.9373(2) 0.34355(18) 0.78233(12) 0.0295(4) Uani 1 1 d . A .
H6 H 0.8719 0.3297 0.7310 0.035 Uiso 1 1 calc R . .
C7 C 0.49906(18) 0.20135(16) 0.87252(11) 0.0233(4) Uani 1 1 d . . .
C8 C 0.45664(19) 0.15285(17) 0.95387(11) 0.0272(4) Uani 1 1 d . A .
H8 H 0.5191 0.1634 1.0069 0.033 Uiso 1 1 calc R . .
C9 C 0.32355(19) 0.08897(16) 0.95835(11) 0.0266(4) Uani 1 1 d . . .
H9 H 0.2954 0.0549 1.0141 0.032 Uiso 1 1 calc R A .
C10 C 0.2319(2) 0.07499(16) 0.88138(12) 0.0265(4) Uani 1 1 d . A .
H10 H 0.1395 0.0330 0.8847 0.032 Uiso 1 1 calc R . .
C11 C 0.27401(18) 0.12191(16) 0.79943(11) 0.0240(4) Uani 1 1 d . . .
H11 H 0.2108 0.1115 0.7467 0.029 Uiso 1 1 calc R A .
C12 C 0.40831(18) 0.18406(15) 0.79419(11) 0.0217(4) Uani 1 1 d . A .
C14 C 0.6189(2) 0.40499(17) 0.89550(14) 0.0279(4) Uani 1 1 d . . .
C15 C 0.45410(19) 0.23345(17) 0.70544(11) 0.0262(4) Uani 1 1 d . . .
C16 C 0.96554(19) 0.26511(17) 1.03126(11) 0.0277(4) Uani 1 1 d . . .
H14A H 0.710(3) 0.448(2) 0.8880(15) 0.050(6) Uiso 1 1 d . . .
H14B H 0.595(2) 0.409(2) 0.9553(16) 0.049(6) Uiso 1 1 d . . .
H14C H 0.540(3) 0.440(2) 0.8605(15) 0.047(6) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C13A 1.355(3) . ?
N1A C7 1.448(2) . ?
N1A C14 1.462(2) . ?
C13A O1 1.225(2) . ?
C13A C1 1.511(3) . ?
N1B C13B 1.35(4) . ?
N1B C14 1.48(3) . ?
N1B C1 1.67(3) . ?
C13B O1 1.25(3) . ?
C13B C7 1.60(3) . ?
F1 C15 1.3349(19) . ?
F2 C15 1.338(2) . ?
F3 C15 1.339(2) . ?
F4 C16 1.335(2) . ?
F5 C16 1.335(2) . ?
F6 C16 1.339(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.390(2) . ?
C2 C16 1.495(2) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.496(2) . ?
C14 H14A 0.95(3) . ?
C14 H14B 0.92(2) . ?
C14 H14C 0.94(2) . ?

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
C13A N1A C7 117.51(15) . . ?
C13A N1A C14 123.72(17) . . ?
C7 N1A C14 116.50(15) . . ?
O1 C13A N1A 122.71(18) . . ?
O1 C13A C1 121.29(16) . . ?
N1A C13A C1 115.79(16) . . ?
C13B N1B C14 124(3) . . ?
C13B N1B C1 103(2) . . ?
C14 N1B C1 129.8(18) . . ?
O1 C13B N1B 116(3) . . ?
O1 C13B C7 142(2) . . ?
N1B C13B C7 99(2) . . ?
C6 C1 C2 119.18(16) . . ?
C6 C1 C13A 117.84(15) . . ?
C2 C1 C13A 122.84(15) . . ?
C6 C1 N1B 114.6(8) . . ?
C2 C1 N1B 115.3(9) . . ?
C3 C2 C1 119.69(16) . . ?
C3 C2 C16 119.53(15) . . ?
C1 C2 C16 120.74(15) . . ?
C4 C3 C2 120.20(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.46(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.52(16) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.94(16) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C12 119.84(15) . . ?
C8 C7 N1A 119.42(15) . . ?
C12 C7 N1A 120.66(15) . . ?
C8 C7 C13B 110.6(9) . . ?
C12 C7 C13B 116.1(9) . . ?
C7 C8 C9 120.37(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.73(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.39(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.15(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.49(15) . . ?
C11 C12 C15 119.99(15) . . ?
C7 C12 C15 120.51(15) . . ?
N1A C14 H14A 111.1(14) . . ?
N1B C14 H14A 80.8(17) . . ?
N1A C14 H14B 108.3(15) . . ?
N1B C14 H14B 107.6(17) . . ?
H14A C14 H14B 109.1(19) . . ?
N1A C14 H14C 108.8(14) . . ?
N1B C14 H14C 135.4(17) . . ?
H14A C14 H14C 111.3(19) . . ?
H14B C14 H14C 108.1(19) . . ?
F1 C15 F2 106.18(14) . . ?
F1 C15 F3 105.62(14) . . ?
F2 C15 F3 106.04(14) . . ?
F1 C15 C12 112.42(14) . . ?
F2 C15 C12 113.25(14) . . ?
F3 C15 C12 112.72(14) . . ?
F4 C16 F5 105.95(14) . . ?
F4 C16 F6 106.18(15) . . ?
F5 C16 F6 105.94(14) . . ?
F4 C16 C2 112.93(14) . . ?
F5 C16 C2 112.37(15) . . ?
F6 C16 C2 112.90(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1A C13A O1 4.3(2) . . . . ?
C14 N1A C13A O1 166.53(17) . . . . ?
C7 N1A C13A C1 179.07(14) . . . . ?
C14 N1A C13A C1 -18.7(2) . . . . ?
C14 N1B C13B O1 -174.4(16) . . . . ?
C1 N1B C13B O1 24(3) . . . . ?
C14 N1B C13B C7 -12(3) . . . . ?
C1 N1B C13B C7 -173.8(12) . . . . ?
N1A C13A O1 C13B 4.9(17) . . . . ?
C1 C13A O1 C13B -169.6(18) . . . . ?
N1B C13B O1 C13A -10.7(13) . . . . ?
C7 C13B O1 C13A -162(4) . . . . ?
O1 C13A C1 C6 94.3(2) . . . . ?
N1A C13A C1 C6 -80.5(2) . . . . ?
O1 C13A C1 C2 -81.3(2) . . . . ?
N1A C13A C1 C2 103.8(2) . . . . ?
O1 C13A C1 N1B -170.8(14) . . . . ?
N1A C13A C1 N1B 14.3(14) . . . . ?
C13B N1B C1 C6 96.5(17) . . . . ?
C14 N1B C1 C6 -64(2) . . . . ?
C13B N1B C1 C2 -119.4(16) . . . . ?
C14 N1B C1 C2 80(2) . . . . ?
C13B N1B C1 C13A -7.7(11) . . . . ?
C14 N1B C1 C13A -168(3) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C13A C1 C2 C3 174.52(16) . . . . ?
N1B C1 C2 C3 -143.5(10) . . . . ?
C6 C1 C2 C16 -178.86(16) . . . . ?
C13A C1 C2 C16 -3.3(3) . . . . ?
N1B C1 C2 C16 38.7(10) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C16 C2 C3 C4 179.01(16) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C13A C1 C6 C5 -175.54(17) . . . . ?
N1B C1 C6 C5 143.0(10) . . . . ?
C13A N1A C7 C8 81.2(2) . . . . ?
C14 N1A C7 C8 -82.3(2) . . . . ?
C13A N1A C7 C12 -102.24(19) . . . . ?
C14 N1A C7 C12 94.2(2) . . . . ?
C13A N1A C7 C13B -6.8(14) . . . . ?
C14 N1A C7 C13B -170.3(14) . . . . ?
O1 C13B C7 C8 54(3) . . . . ?
N1B C13B C7 C8 -100.1(17) . . . . ?
O1 C13B C7 C12 -87(3) . . . . ?
N1B C13B C7 C12 118.9(15) . . . . ?
O1 C13B C7 N1A 166(4) . . . . ?
N1B C13B C7 N1A 11.4(11) . . . . ?
C12 C7 C8 C9 -1.0(3) . . . . ?
N1A C7 C8 C9 175.55(16) . . . . ?
C13B C7 C8 C9 -140.4(12) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C7 -1.4(3) . . . . ?
C10 C11 C12 C15 179.37(16) . . . . ?
C8 C7 C12 C11 2.2(3) . . . . ?
N1A C7 C12 C11 -174.39(15) . . . . ?
C13B C7 C12 C11 139.4(12) . . . . ?
C8 C7 C12 C15 -178.65(16) . . . . ?
N1A C7 C12 C15 4.8(2) . . . . ?
C13B C7 C12 C15 -41.4(12) . . . . ?
C13A N1A C14 N1B -3.5(16) . . . . ?
C7 N1A C14 N1B 158.9(17) . . . . ?
C13B N1B C14 N1A -3.8(14) . . . . ?
C1 N1B C14 N1A 153(3) . . . . ?
C11 C12 C15 F1 -2.7(2) . . . . ?
C7 C12 C15 F1 178.09(15) . . . . ?
C11 C12 C15 F2 117.64(17) . . . . ?
C7 C12 C15 F2 -61.5(2) . . . . ?
C11 C12 C15 F3 -121.97(17) . . . . ?
C7 C12 C15 F3 58.8(2) . . . . ?
C3 C2 C16 F4 140.12(16) . . . . ?
C1 C2 C16 F4 -42.1(2) . . . . ?
C3 C2 C16 F5 20.3(2) . . . . ?
C1 C2 C16 F5 -161.88(15) . . . . ?
C3 C2 C16 F6 -99.40(19) . . . . ?
C1 C2 C16 F6 78.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_NM12
_database_code_depnum_ccdc_archive 'CCDC 1025681'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N O'
_chemical_formula_sum            'C16 H11 F6 N O'
_chemical_formula_weight         347.26

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                   9.0978(7)
_cell_length_b                   22.1735(15)
_cell_length_c                   7.9449(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.946(4)
_cell_angle_gamma                90.00
_cell_volume                     1568.02(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3184
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.31

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(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            13654
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2767
_reflns_number_gt                2117
_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          
; 
 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. 
;

_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)+(0.0634P)²+0.4580P] 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     SHELXL
_refine_ls_extinction_coef       0.051(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2767
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL NM12R in P2(1)/c
CELL 0.71073 9.0978 22.1735 7.9449 90.000 101.946 90.000
ZERR 4.00 0.0007 0.0015 0.0005 0.000 0.004 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O F
UNIT 64 44 4 4 24
TEMP 24
ACTA
L.S. 12
SIZE 0.33 0.24 0.15
OMIT -1 50
FMAP 2
PLAN 5
BOND $H
WGHT    0.063400    0.458000
EXTI    0.050584
FVAR       0.29081   0.53080
F1    5    1.226642    1.024223    0.336514    11.00000    0.25312    0.07589 =
         0.11112   -0.04145    0.07027   -0.05034
F2    5    1.099032    0.955739    0.415932    11.00000    0.11103    0.11829 =
         0.07168   -0.02717    0.04267   -0.01173
F3    5    1.330745    0.943378    0.441741    11.00000    0.10228    0.19400 =
         0.08074   -0.04578   -0.01900    0.02472
PART -1
F4A   5    0.549992    0.879117   -0.270037    21.00000    0.14732    0.20087 =
         0.12396    0.04719   -0.03938   -0.00751
F5A   5    0.535572    0.789779   -0.200576    21.00000    0.22207    0.25751 =
         0.13096    0.01527   -0.02400   -0.19186
F6A   5    0.721380    0.819558   -0.270059    21.00000    0.11990    0.25168 =
         0.07938   -0.04363   -0.00038   -0.02106
PART -2
F4B   5    0.699540    0.849403   -0.283935   -21.00000    0.23032    0.25634 =
         0.06737    0.00068    0.04485   -0.15228
F6B   5    0.479489    0.837097   -0.227406   -21.00000    0.07789    0.21203 =
         0.11608   -0.04103   -0.02692    0.03037
F5B   5    0.627380    0.767009   -0.193507   -21.00000    0.13997    0.12052 =
         0.13843   -0.07015   -0.02202    0.00738
PART 0
 
N1    3    1.163245    0.835982    0.271531    11.00000    0.04945    0.05142 =
         0.06752    0.01463    0.01457    0.00641
O1    4    1.051702    0.790956    0.466074    11.00000    0.08487    0.07474 =
         0.07661    0.02745    0.02697    0.00708
C1    1    0.890863    0.845089    0.246681    11.00000    0.05082    0.04813 =
         0.05978    0.00191    0.02191   -0.00342
C2    1    0.804936    0.878582    0.337442    11.00000    0.06165    0.07305 =
         0.07294   -0.01083    0.02732   -0.00223
AFIX  43
H2    2    0.843580    0.888368    0.451872    11.00000   -1.20000
AFIX   0
C3    1    0.663299    0.897517    0.260413    11.00000    0.05800    0.09018 =
         0.10340   -0.01520    0.03344    0.00532
AFIX  43
H3    2    0.607328    0.920527    0.322289    11.00000   -1.20000
AFIX   0
C4    1    0.604098    0.882630    0.092659    11.00000    0.04551    0.08320 =
         0.10740    0.00741    0.01804    0.00041
AFIX  43
H4    2    0.508627    0.895912    0.040225    11.00000   -1.20000
AFIX   0
C5    1    0.686848    0.847795    0.001692    11.00000    0.05155    0.07433 =
         0.07175    0.00135    0.01400   -0.01371
C6    1    0.830233    0.829081    0.078382    11.00000    0.05215    0.06105 =
         0.06308   -0.00369    0.02068   -0.00445
AFIX  43
H6    2    0.885772    0.805754    0.016764    11.00000   -1.20000
AFIX   0
C7    1    1.164089    0.877092    0.132397    11.00000    0.04146    0.04754 =
         0.05183    0.00288    0.01414    0.00229
C8    1    1.187739    0.938778    0.161096    11.00000    0.05633    0.04834 =
         0.05039   -0.00134    0.01607   -0.00128
C9    1    1.193316    0.975738    0.022769    11.00000    0.09037    0.05077 =
         0.07248    0.00815    0.02908   -0.00169
AFIX  43
H9    2    1.208004    1.016950    0.040461    11.00000   -1.20000
AFIX   0
C10   1    1.177536    0.952716   -0.140846    11.00000    0.09499    0.08291 =
         0.05630    0.01517    0.02359    0.00180
AFIX  43
H10   2    1.180673    0.978333   -0.232722    11.00000   -1.20000
AFIX   0
C11   1    1.157380    0.892545   -0.167954    11.00000    0.07359    0.09294 =
         0.05066   -0.00939    0.01894   -0.00391
AFIX  43
H11   2    1.147910    0.876867   -0.278250    11.00000   -1.20000
AFIX   0
C12   1    1.150975    0.854835   -0.032545    11.00000    0.05842    0.05744 =
         0.06743   -0.01469    0.02037   -0.00324
AFIX  43
H12   2    1.137599    0.813657   -0.052144    11.00000   -1.20000
AFIX   0
C13   1    1.041439    0.822160    0.336655    11.00000    0.06195    0.04463 =
         0.05652    0.00407    0.01819    0.00157
C14   1    1.306193    0.805684    0.342059    11.00000    0.06178    0.09205 =
         0.12231    0.04822    0.01911    0.02366
AFIX 137
H14A  2    1.328733    0.809558    0.465070    11.00000   -1.50000
H14B  2    1.384948    0.823933    0.295751    11.00000   -1.50000
H14C  2    1.298378    0.763748    0.311478    11.00000   -1.50000
AFIX   0
C15   1    1.211899    0.965091    0.336785    11.00000    0.08105    0.06522 =
         0.06284   -0.01132    0.02016   -0.01168
C16   1    0.623344    0.830159   -0.179756    11.00000    0.07073    0.13195 =
         0.08447   -0.00281    0.00741   -0.01982
HKLF   4
 
REM  NM12R in P2(1)/c
REM R1 =  0.0482 for   2117 Fo > 4sig(Fo)  and  0.0637 for all   2767 data
REM    247 parameters refined using      0 restraints
 
END  
     
WGHT      0.0634      0.4580 
REM Highest difference peak  0.363,  deepest hole -0.222,  1-sigma level  0.036
Q1    1   1.3434  0.9899  0.3573  11.00000  0.05    0.36
Q2    1   1.2088  0.9259  0.4619  11.00000  0.05    0.30
Q3    1   1.1240  1.0011  0.3675  11.00000  0.05    0.25
Q4    1   1.2862  0.7772  0.4370  11.00000  0.05    0.22
Q5    1   1.1367  0.9102  0.1449  11.00000  0.05    0.20
;

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 1.2266(3) 1.02422(8) 0.3365(2) 0.1420(9) Uani 1 1 d . . .
F2 F 1.09903(19) 0.95574(8) 0.41593(18) 0.0969(6) Uani 1 1 d . . .
F3 F 1.3307(2) 0.94338(11) 0.4417(2) 0.1311(8) Uani 1 1 d . . .
F4A F 0.5500(15) 0.8791(5) -0.2700(9) 0.167(3) Uani 0.531(13) 1 d P A -1
F5A F 0.536(2) 0.7898(8) -0.2006(9) 0.212(7) Uani 0.531(13) 1 d P A -1
F6A F 0.7214(12) 0.8196(7) -0.2701(14) 0.153(5) Uani 0.531(13) 1 d P A -1
F4B F 0.700(2) 0.8494(9) -0.2839(15) 0.183(9) Uani 0.469(13) 1 d P A -2
F6B F 0.4795(8) 0.8371(7) -0.2274(13) 0.142(6) Uani 0.469(13) 1 d P A -2
F5B F 0.6274(12) 0.7670(4) -0.1935(11) 0.140(4) Uani 0.469(13) 1 d P A -2
N1 N 1.16325(18) 0.83598(7) 0.2715(2) 0.0558(5) Uani 1 1 d . . .
O1 O 1.05170(19) 0.79096(7) 0.4661(2) 0.0773(5) Uani 1 1 d . . .
C1 C 0.8909(2) 0.84509(8) 0.2467(3) 0.0514(5) Uani 1 1 d . . .
C2 C 0.8049(3) 0.87858(10) 0.3374(3) 0.0673(6) Uani 1 1 d . . .
H2 H 0.8436 0.8884 0.4519 0.081 Uiso 1 1 calc R . .
C3 C 0.6633(3) 0.89752(12) 0.2604(4) 0.0814(8) Uani 1 1 d . . .
H3 H 0.6073 0.9205 0.3223 0.098 Uiso 1 1 calc R . .
C4 C 0.6041(3) 0.88263(12) 0.0927(4) 0.0784(7) Uani 1 1 d . . .
H4 H 0.5086 0.8959 0.0402 0.094 Uiso 1 1 calc R . .
C5 C 0.6868(2) 0.84780(11) 0.0017(3) 0.0657(6) Uani 1 1 d . A .
C6 C 0.8302(2) 0.82908(10) 0.0784(3) 0.0575(5) Uani 1 1 d . . .
H6 H 0.8858 0.8058 0.0168 0.069 Uiso 1 1 calc R . .
C7 C 1.1641(2) 0.87709(8) 0.1324(2) 0.0463(5) Uani 1 1 d . . .
C8 C 1.1877(2) 0.93878(9) 0.1611(2) 0.0510(5) Uani 1 1 d . . .
C9 C 1.1933(3) 0.97574(10) 0.0228(3) 0.0694(6) Uani 1 1 d . . .
H9 H 1.2080 1.0170 0.0405 0.083 Uiso 1 1 calc R . .
C10 C 1.1775(3) 0.95272(13) -0.1408(3) 0.0769(7) Uani 1 1 d . . .
H10 H 1.1807 0.9783 -0.2327 0.092 Uiso 1 1 calc R . .
C11 C 1.1574(3) 0.89254(12) -0.1680(3) 0.0715(7) Uani 1 1 d . . .
H11 H 1.1479 0.8769 -0.2782 0.086 Uiso 1 1 calc R . .
C12 C 1.1510(2) 0.85484(10) -0.0325(3) 0.0600(6) Uani 1 1 d . . .
H12 H 1.1376 0.8137 -0.0521 0.072 Uiso 1 1 calc R . .
C13 C 1.0414(2) 0.82216(9) 0.3367(3) 0.0535(5) Uani 1 1 d . . .
C14 C 1.3062(3) 0.80568(13) 0.3421(4) 0.0920(9) Uani 1 1 d . . .
H14A H 1.3287 0.8096 0.4651 0.138 Uiso 1 1 calc R . .
H14B H 1.3849 0.8239 0.2958 0.138 Uiso 1 1 calc R . .
H14C H 1.2984 0.7637 0.3115 0.138 Uiso 1 1 calc R . .
C15 C 1.2119(3) 0.96509(11) 0.3368(3) 0.0689(6) Uani 1 1 d . . .
C16 C 0.6233(4) 0.83016(19) -0.1798(4) 0.0970(10) 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 1.318(3) . ?
F2 C15 1.327(3) . ?
F3 C15 1.313(3) . ?
F4A C16 1.393(7) . ?
F5A C16 1.188(6) . ?
F6A C16 1.277(12) . ?
F4B C16 1.259(11) . ?
F6B C16 1.294(7) . ?
F5B C16 1.406(8) . ?
N1 C13 1.352(3) . ?
N1 C7 1.434(2) . ?
N1 C14 1.468(3) . ?
O1 C13 1.227(2) . ?
C1 C6 1.383(3) . ?
C1 C2 1.384(3) . ?
C1 C13 1.497(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 C16 1.490(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.382(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.380(3) . ?
C8 C15 1.487(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
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
C13 N1 C7 125.09(16) . . ?
C13 N1 C14 118.81(17) . . ?
C7 N1 C14 116.07(16) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 C13 121.13(18) . . ?
C2 C1 C13 119.55(19) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C16 120.6(2) . . ?
C6 C5 C16 119.2(2) . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C7 C8 119.00(18) . . ?
C12 C7 N1 119.39(17) . . ?
C8 C7 N1 121.48(17) . . ?
C9 C8 C7 118.79(18) . . ?
C9 C8 C15 119.47(19) . . ?
C7 C8 C15 121.72(18) . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 121.1(2) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
O1 C13 N1 121.50(19) . . ?
O1 C13 C1 119.68(18) . . ?
N1 C13 C1 118.81(17) . . ?
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 . . ?
F3 C15 F1 107.2(2) . . ?
F3 C15 F2 105.0(2) . . ?
F1 C15 F2 104.2(2) . . ?
F3 C15 C8 113.3(2) . . ?
F1 C15 C8 112.6(2) . . ?
F2 C15 C8 113.90(19) . . ?
F5A C16 F4B 127.5(8) . . ?
F5A C16 F6A 108.1(9) . . ?
F4B C16 F6B 115.4(8) . . ?
F6A C16 F6B 129.7(7) . . ?
F5A C16 F4A 106.2(7) . . ?
F4B C16 F4A 70.6(8) . . ?
F6A C16 F4A 99.8(7) . . ?
F4B C16 F5B 105.1(10) . . ?
F4A C16 F5B 138.9(4) . . ?
F5A C16 C5 116.6(4) . . ?
F4B C16 C5 113.0(7) . . ?
F6A C16 C5 114.6(5) . . ?
F6B C16 C5 114.7(4) . . ?
F4A C16 C5 110.0(4) . . ?
F5B C16 C5 109.0(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_NM22
_database_code_depnum_ccdc_archive 'CCDC 1025682'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N O'
_chemical_formula_sum            'C16 H11 F6 N O'
_chemical_formula_weight         347.26

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                   8.3764(5)
_cell_length_b                   23.2362(17)
_cell_length_c                   7.9755(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.567(2)
_cell_angle_gamma                90.00
_cell_volume                     1509.00(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8183
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.67

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9198
_exptl_absorpt_correction_T_max  0.9485
_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            21987
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2652
_reflns_number_gt                2199
_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          
; 
 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. 
;

_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)+(0.0466P)²+1.1532P] 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         2652
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL NM22 in P2(1)/c
CELL 0.71073 8.3764 23.2362 7.9755 90.000 103.567 90.000
ZERR 4.00 0.0005 0.0017 0.0006 0.000 0.002 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O F
UNIT 64 44 4 4 24
TEMP -153
ACTA
L.S. 12
SIZE 0.43 0.31 0.22
OMIT -1 50
FMAP 2
PLAN 5
BOND $H
CONF
WGHT    0.046600    1.153200
FVAR       0.17430   0.55872
PART -1
 
F1A   5    0.658192    0.422631   -0.376775    21.00000    0.25545    0.06208 =
         0.02654   -0.01776    0.05092   -0.07403
F2A   5    0.873934    0.467824   -0.251806    21.00000    0.05164    0.07952 =
         0.05723    0.03890    0.03808    0.02351
F3A   5    0.658375    0.512901   -0.296079    21.00000    0.08192    0.02129 =
         0.03336    0.00168    0.01850   -0.00581
PART -2
F1B   5    0.581489    0.429976   -0.386531   -21.00000    0.07338    0.05915 =
         0.02177    0.00694   -0.00253   -0.02913
F2B   5    0.831870    0.446736   -0.307723   -21.00000    0.04658    0.10477 =
         0.03749    0.02598    0.02629    0.03294
F3B   5    0.639874    0.507783   -0.302389   -21.00000    0.03785    0.07307 =
         0.05596    0.04752    0.01761    0.03101
PART 0
F4    5    0.038208    0.340184    0.525102    11.00000    0.11043    0.06534 =
         0.07007   -0.01360    0.07120   -0.03288
F5    5    0.063360    0.429128    0.476656    11.00000    0.05276    0.05832 =
         0.03467   -0.00632    0.01615    0.01888
F6    5    0.267860    0.383296    0.622434    11.00000    0.05176    0.09438 =
         0.02082   -0.00781    0.00266    0.02631
N1    3    0.654022    0.301404    0.138013    11.00000    0.02541    0.01669 =
         0.02323    0.00111    0.00796    0.00408
O1    4    0.523018    0.227923    0.235089    11.00000    0.03780    0.02041 =
         0.03217    0.00792    0.00775    0.00148
C1    1    0.378539    0.316461    0.181913    11.00000    0.02195    0.01621 =
         0.02091    0.00119    0.00428   -0.00503
C2    1    0.330526    0.329546    0.332728    11.00000    0.02454    0.02269 =
         0.01876    0.00304    0.00338   -0.00471
AFIX  43
H2    2    0.391251    0.315289    0.440529    11.00000   -1.20000
AFIX   0
C3    1    0.192829    0.363687    0.324335    11.00000    0.02393    0.02686 =
         0.02242   -0.00089    0.00760   -0.00627
C4    1    0.100854    0.383358    0.166311    11.00000    0.01816    0.03014 =
         0.02692    0.00056    0.00639   -0.00229
AFIX  43
H4    2    0.006852    0.406759    0.161292    11.00000   -1.20000
AFIX   0
C5    1    0.147227    0.368608    0.016673    11.00000    0.02156    0.03141 =
         0.01943    0.00334    0.00183   -0.00240
AFIX  43
H5    2    0.083025    0.381126   -0.091674    11.00000   -1.20000
AFIX   0
C6    1    0.286464    0.335740    0.023324    11.00000    0.02336    0.02353 =
         0.01977    0.00068    0.00632   -0.00516
AFIX  43
H6    2    0.318973    0.326398   -0.079779    11.00000   -1.20000
AFIX   0
C7    1    0.668734    0.361876    0.106812    11.00000    0.01616    0.01939 =
         0.02340    0.00054    0.00598    0.00231
C8    1    0.673864    0.380548   -0.056731    11.00000    0.02049    0.02069 =
         0.02075   -0.00392    0.00561    0.00057
AFIX  43
H8    2    0.664111    0.353823   -0.148725    11.00000   -1.20000
AFIX   0
C9    1    0.693421    0.438755   -0.084440    11.00000    0.02294    0.02274 =
         0.02372    0.00040    0.00755    0.00009
C10   1    0.705907    0.478397    0.048573    11.00000    0.02718    0.01701 =
         0.03157   -0.00199    0.00888   -0.00247
AFIX  43
H10   2    0.718329    0.518237    0.028077    11.00000   -1.20000
AFIX   0
C11   1    0.700032    0.459146    0.211016    11.00000    0.02695    0.02168 =
         0.02758   -0.00873    0.00855   -0.00109
AFIX  43
H11   2    0.708227    0.485897    0.302723    11.00000   -1.20000
AFIX   0
C12   1    0.682236    0.400981    0.240683    11.00000    0.02057    0.02714 =
         0.02015   -0.00156    0.00637    0.00054
AFIX  43
H12   2    0.679293    0.387913    0.352784    11.00000   -1.20000
AFIX   0
C13   1    0.524897    0.278492    0.189595    11.00000    0.02844    0.02002 =
         0.01375    0.00013    0.00206   -0.00140
C14   1    0.790761    0.263918    0.123049    11.00000    0.03205    0.02367 =
         0.03212    0.00157    0.01154    0.00797
AFIX 137
H14A  2    0.873814    0.263863    0.232441    11.00000   -1.50000
H14B  2    0.839798    0.278165    0.030875    11.00000   -1.50000
H14C  2    0.750083    0.224666    0.095827    11.00000   -1.50000
AFIX   0
C15   1    0.703829    0.458530   -0.259741    11.00000    0.05100    0.02531 =
         0.03280    0.00079    0.01879   -0.00007
C16   1    0.141810    0.378638    0.486573    11.00000    0.03372    0.04032 =
         0.02536   -0.00019    0.01097    0.00037
HKLF   4
 
REM  NM22 in P2(1)/c
REM R1 =  0.0410 for   2199 Fo > 4sig(Fo)  and  0.0534 for all   2652 data
REM    246 parameters refined using      0 restraints
 
END  
     
WGHT      0.0466      1.1533 
REM Highest difference peak  0.497,  deepest hole -0.343,  1-sigma level  0.045
Q1    1   0.1400  0.3142  0.5814  11.00000  0.05    0.50
Q2    1   0.0079  0.3943  0.4797  11.00000  0.05    0.37
Q3    1   0.6666  0.4579 -0.0400  11.00000  0.05    0.23
Q4    1   0.2507  0.3408  0.6152  11.00000  0.05    0.22
Q5    1   0.7991  0.3994 -0.3185  11.00000  0.05    0.21
;

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
F1A F 0.658(5) 0.4226(6) -0.3768(12) 0.112(7) Uani 0.56(4) 1 d P A -1
F2A F 0.8739(16) 0.4678(6) -0.252(2) 0.059(3) Uani 0.56(4) 1 d P A -1
F3A F 0.6584(13) 0.5129(3) -0.2961(11) 0.045(2) Uani 0.56(4) 1 d P A -1
F1B F 0.5815(10) 0.4300(5) -0.3865(12) 0.054(2) Uani 0.44(4) 1 d P A -2
F2B F 0.8319(19) 0.4467(11) -0.3077(18) 0.060(4) Uani 0.44(4) 1 d P A -2
F3B F 0.6399(16) 0.5078(6) -0.3024(15) 0.055(3) Uani 0.44(4) 1 d P A -2
F4 F 0.0382(2) 0.34018(7) 0.5251(2) 0.0737(6) Uani 1 1 d . . .
F5 F 0.06336(17) 0.42913(6) 0.47666(17) 0.0476(4) Uani 1 1 d . . .
F6 F 0.26786(18) 0.38330(7) 0.62243(16) 0.0566(4) Uani 1 1 d . . .
N1 N 0.65402(19) 0.30140(6) 0.13801(19) 0.0214(4) Uani 1 1 d . . .
O1 O 0.52302(17) 0.22792(6) 0.23509(18) 0.0302(3) Uani 1 1 d . . .
C1 C 0.3785(2) 0.31646(7) 0.1819(2) 0.0198(4) Uani 1 1 d . . .
C2 C 0.3305(2) 0.32955(8) 0.3327(2) 0.0223(4) Uani 1 1 d . . .
H2 H 0.3913 0.3153 0.4405 0.027 Uiso 1 1 calc R . .
C3 C 0.1928(2) 0.36369(8) 0.3243(2) 0.0240(4) Uani 1 1 d . . .
C4 C 0.1009(2) 0.38336(8) 0.1663(2) 0.0249(4) Uani 1 1 d . . .
H4 H 0.0069 0.4068 0.1613 0.030 Uiso 1 1 calc R . .
C5 C 0.1472(2) 0.36861(8) 0.0167(2) 0.0246(4) Uani 1 1 d . . .
H5 H 0.0830 0.3811 -0.0917 0.030 Uiso 1 1 calc R . .
C6 C 0.2865(2) 0.33574(8) 0.0233(2) 0.0220(4) Uani 1 1 d . . .
H6 H 0.3190 0.3264 -0.0798 0.026 Uiso 1 1 calc R . .
C7 C 0.6687(2) 0.36188(8) 0.1068(2) 0.0194(4) Uani 1 1 d . . .
C8 C 0.6739(2) 0.38055(8) -0.0567(2) 0.0205(4) Uani 1 1 d . . .
H8 H 0.6641 0.3538 -0.1487 0.025 Uiso 1 1 calc R . .
C9 C 0.6934(2) 0.43876(8) -0.0844(2) 0.0228(4) Uani 1 1 d . A .
C10 C 0.7059(2) 0.47840(8) 0.0486(3) 0.0249(4) Uani 1 1 d . . .
H10 H 0.7183 0.5182 0.0281 0.030 Uiso 1 1 calc R . .
C11 C 0.7000(2) 0.45915(8) 0.2110(3) 0.0250(4) Uani 1 1 d . . .
H11 H 0.7082 0.4859 0.3027 0.030 Uiso 1 1 calc R . .
C12 C 0.6822(2) 0.40098(8) 0.2407(2) 0.0224(4) Uani 1 1 d . . .
H12 H 0.6793 0.3879 0.3528 0.027 Uiso 1 1 calc R . .
C13 C 0.5249(2) 0.27849(8) 0.1896(2) 0.0212(4) Uani 1 1 d . . .
C14 C 0.7908(2) 0.26392(9) 0.1230(3) 0.0286(5) Uani 1 1 d . . .
H14A H 0.8738 0.2639 0.2324 0.043 Uiso 1 1 calc R . .
H14B H 0.8398 0.2782 0.0309 0.043 Uiso 1 1 calc R . .
H14C H 0.7501 0.2247 0.0958 0.043 Uiso 1 1 calc R . .
C15 C 0.7038(3) 0.45853(9) -0.2597(3) 0.0349(5) Uani 1 1 d . . .
C16 C 0.1418(3) 0.37864(9) 0.4866(3) 0.0325(5) 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
F1A C15 1.243(8) . ?
F2A C15 1.428(12) . ?
F3A C15 1.332(8) . ?
F1B C15 1.424(9) . ?
F2B C15 1.251(8) . ?
F3B C15 1.276(10) . ?
F4 C16 1.331(3) . ?
F5 C16 1.338(2) . ?
F6 C16 1.328(3) . ?
N1 C13 1.353(2) . ?
N1 C7 1.437(2) . ?
N1 C14 1.466(2) . ?
O1 C13 1.231(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.392(3) . ?
C1 C13 1.500(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 C16 1.496(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 C12 1.386(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C9 C15 1.494(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 122.98(15) . . ?
C13 N1 C14 119.11(15) . . ?
C7 N1 C14 117.80(15) . . ?
C2 C1 C6 120.35(17) . . ?
C2 C1 C13 119.57(16) . . ?
C6 C1 C13 119.98(16) . . ?
C1 C2 C3 119.31(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.57(18) . . ?
C2 C3 C16 119.58(18) . . ?
C4 C3 C16 119.84(18) . . ?
C5 C4 C3 119.52(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.57(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.64(17) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 120.34(17) . . ?
C8 C7 N1 119.49(16) . . ?
C12 C7 N1 120.15(16) . . ?
C7 C8 C9 119.13(17) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 121.02(17) . . ?
C8 C9 C15 118.97(17) . . ?
C10 C9 C15 120.00(17) . . ?
C11 C10 C9 119.20(18) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.29(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.02(17) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
O1 C13 N1 122.11(17) . . ?
O1 C13 C1 120.44(17) . . ?
N1 C13 C1 117.39(15) . . ?
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 . . ?
F1A C15 F3B 111.5(17) . . ?
F2B C15 F3B 116.8(13) . . ?
F1A C15 F3A 116.8(13) . . ?
F2B C15 F3A 111.3(12) . . ?
F2B C15 F1B 101.9(11) . . ?
F3B C15 F1B 92.4(8) . . ?
F3A C15 F1B 99.6(6) . . ?
F1A C15 F2A 105.2(10) . . ?
F3B C15 F2A 103.2(9) . . ?
F3A C15 F2A 95.6(7) . . ?
F1B C15 F2A 130.3(7) . . ?
F1A C15 C9 114.9(4) . . ?
F2B C15 C9 117.5(4) . . ?
F3B C15 C9 114.4(6) . . ?
F3A C15 C9 114.8(4) . . ?
F1B C15 C9 109.3(4) . . ?
F2A C15 C9 106.4(6) . . ?
F6 C16 F4 107.64(19) . . ?
F6 C16 F5 105.20(17) . . ?
F4 C16 F5 105.34(18) . . ?
F6 C16 C3 113.01(17) . . ?
F4 C16 C3 112.21(17) . . ?
F5 C16 C3 112.87(17) . . ?

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 -2.2(3) . . . . ?
C13 C1 C2 C3 -178.60(16) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C2 C3 C16 -179.14(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C16 C3 C4 C5 -178.97(18) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C13 C1 C6 C5 177.07(16) . . . . ?
C13 N1 C7 C8 -118.22(19) . . . . ?
C14 N1 C7 C8 65.6(2) . . . . ?
C13 N1 C7 C12 63.6(2) . . . . ?
C14 N1 C7 C12 -112.58(19) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
N1 C7 C8 C9 -177.93(16) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C7 C8 C9 C15 178.23(17) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C15 C9 C10 C11 -178.43(18) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
N1 C7 C12 C11 178.58(16) . . . . ?
C7 N1 C13 O1 -171.33(17) . . . . ?
C14 N1 C13 O1 4.8(3) . . . . ?
C7 N1 C13 C1 11.4(2) . . . . ?
C14 N1 C13 C1 -172.49(16) . . . . ?
C2 C1 C13 O1 64.5(2) . . . . ?
C6 C1 C13 O1 -112.0(2) . . . . ?
C2 C1 C13 N1 -118.19(19) . . . . ?
C6 C1 C13 N1 65.4(2) . . . . ?
C8 C9 C15 F1A 15(2) . . . . ?
C10 C9 C15 F1A -166(2) . . . . ?
C8 C9 C15 F2B -71.5(16) . . . . ?
C10 C9 C15 F2B 107.5(16) . . . . ?
C8 C9 C15 F3B 145.9(8) . . . . ?
C10 C9 C15 F3B -35.1(8) . . . . ?
C8 C9 C15 F3A 154.8(5) . . . . ?
C10 C9 C15 F3A -26.2(6) . . . . ?
C8 C9 C15 F1B 44.0(5) . . . . ?
C10 C9 C15 F1B -137.0(5) . . . . ?
C8 C9 C15 F2A -100.8(7) . . . . ?
C10 C9 C15 F2A 78.2(7) . . . . ?
C2 C3 C16 F6 32.1(3) . . . . ?
C4 C3 C16 F6 -148.83(19) . . . . ?
C2 C3 C16 F4 -89.9(2) . . . . ?
C4 C3 C16 F4 89.2(2) . . . . ?
C2 C3 C16 F5 151.31(18) . . . . ?
C4 C3 C16 F5 -29.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_NM23
_database_code_depnum_ccdc_archive 'CCDC 1025683'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N O'
_chemical_formula_sum            'C16 H11 F6 N O'
_chemical_formula_weight         347.26

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                   11.2958(5)
_cell_length_b                   14.0246(4)
_cell_length_c                   10.4868(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.258(4)
_cell_angle_gamma                90.00
_cell_volume                     1502.48(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7498
_cell_measurement_theta_min      2.4616
_cell_measurement_theta_max      29.3261

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9336
_exptl_absorpt_correction_T_max  0.9542
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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            14260
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2649
_reflns_number_gt                2238
_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          
; 
 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. 
;

_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)+(0.0477P)²+0.7788P] 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         2649
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    NM23 in P 1 21/c 1
CELL   0.71073  11.2958  14.0246  10.4868  90.000 115.258  90.000
ZERR     4       0.0005   0.0004   0.0003   0.000   0.004   0.000
LATT  1
SYMM -X, 0.50000+Y, 0.50000-Z
SFAC    C   H   N   O   F
UNIT    64  44   4   4  24
MERG    2
L.S.    12
SIZE 0.4 0.25 0.25
OMIT -1 50
EADP F1B F2B F3B
EADP F4B F5B F6B
ACTA
HTAB
BOND $H
CONF
TEMP -153
FMAP    2
PLAN    5
 
WGHT    0.047700    0.778800
FVAR       6.54982   0.93018   0.91128
PART -1
F1A   5    0.079558    0.450441   -0.330396    21.00000    0.06145    0.06396 =
         0.03367   -0.00533   -0.01968    0.01235
F2A   5    0.254224    0.382585   -0.308125    21.00000    0.05433    0.11886 =
         0.04559   -0.04439    0.03495   -0.03522
F3A   5    0.124137    0.312666   -0.240626    21.00000    0.08352    0.04405 =
         0.02911   -0.01006    0.01894   -0.03266
 
F4A   5    0.989708    0.285540    0.445386    31.00000    0.01999    0.10131 =
         0.04433   -0.03249   -0.00173    0.01378
F5A   5    0.881960    0.166450    0.323699    31.00000    0.04935    0.02965 =
         0.09469   -0.00390    0.04219    0.00824
F6A   5    0.887543    0.295362    0.221739    31.00000    0.04431    0.06924 =
         0.05185    0.01957    0.03459    0.01658
PART -2
F1B   5    0.157600    0.444179   -0.350670   -21.00000    0.05161    0.03887 =
         0.03785   -0.00654    0.01886   -0.00939
F2B   5    0.253764    0.320504   -0.259306   -21.00000    0.05161    0.03887 =
         0.03785   -0.00654    0.01886   -0.00939
F3B   5    0.071152    0.361028   -0.265263   -21.00000    0.05161    0.03887 =
         0.03785   -0.00654    0.01886   -0.00939
 
F4B   5    0.966587    0.317879    0.408994   -31.00000    0.02942    0.08952 =
         0.06313    0.00032    0.01702    0.01649
F5B   5    0.924338    0.183498    0.423291   -31.00000    0.02942    0.08952 =
         0.06313    0.00032    0.01702    0.01649
F6B   5    0.871135    0.242674    0.229816   -31.00000    0.02942    0.08952 =
         0.06313    0.00032    0.01702    0.01649
PART 0
 
N1    3    0.301455    0.406172    0.268794    11.00000    0.02116    0.02954 =
         0.01914    0.00273    0.00964    0.00047
O1    4    0.411764    0.368571    0.500192    11.00000    0.03471    0.04739 =
         0.02059    0.00586    0.01470    0.00758
C1    1    0.529914    0.353981    0.361871    11.00000    0.02554    0.01962 =
         0.01566    0.00461    0.00866    0.00224
C2    1    0.650314    0.387921    0.457679    11.00000    0.02960    0.02532 =
         0.01728   -0.00209    0.00937    0.00029
AFIX  43
H2    2    0.654451    0.431702    0.528589    11.00000   -1.20000
AFIX   0
C3    1    0.764697    0.358674    0.451131    11.00000    0.02370    0.02823 =
         0.01970    0.00008    0.00522   -0.00198
AFIX  43
H3    2    0.846947    0.382587    0.516570    11.00000   -1.20000
AFIX   0
C4    1    0.757926    0.294092    0.348020    11.00000    0.02499    0.02262 =
         0.01902    0.00348    0.00832    0.00208
C5    1    0.637880    0.260627    0.250696    11.00000    0.02841    0.01922 =
         0.01921    0.00006    0.00967    0.00094
AFIX  43
H5    2    0.634000    0.217203    0.179488    11.00000   -1.20000
AFIX   0
C6    1    0.523614    0.290278    0.256920    11.00000    0.02326    0.01978 =
         0.01714    0.00210    0.00567   -0.00098
AFIX  43
H6    2    0.441307    0.267388    0.190097    11.00000   -1.20000
AFIX   0
C7    1    0.308907    0.444863    0.145944    11.00000    0.01942    0.02351 =
         0.01937    0.00350    0.00870    0.00467
C8    1    0.240264    0.402004    0.015520    11.00000    0.01837    0.02485 =
         0.02370    0.00114    0.00742   -0.00174
AFIX  43
H8    2    0.188811    0.346749    0.007159    11.00000   -1.20000
AFIX   0
C9    1    0.247791    0.440869   -0.102250    11.00000    0.02015    0.02632 =
         0.02001    0.00116    0.00675    0.00253
C10   1    0.321243    0.522251   -0.091024    11.00000    0.03188    0.02533 =
         0.02358    0.00542    0.01194    0.00129
AFIX  43
H10   2    0.326040    0.548361   -0.172278    11.00000   -1.20000
AFIX   0
C11   1    0.387298    0.565118    0.038609    11.00000    0.03583    0.02304 =
         0.02732    0.00133    0.01274   -0.00555
AFIX  43
H11   2    0.436665    0.621427    0.046371    11.00000   -1.20000
AFIX   0
C12   1    0.381985    0.526415    0.157626    11.00000    0.02735    0.02187 =
         0.02160   -0.00144    0.00761    0.00100
AFIX  43
H12   2    0.428333    0.555731    0.246979    11.00000   -1.20000
AFIX   0
C13   1    0.409882    0.378338    0.383418    11.00000    0.02933    0.02113 =
         0.01952    0.00012    0.01098   -0.00002
C14   1    0.176283    0.417020    0.278809    11.00000    0.02442    0.03893 =
         0.02874    0.00072    0.01364   -0.00021
AFIX 137
H14A  2    0.184156    0.390475    0.368531    11.00000   -1.50000
H14B  2    0.107480    0.383003    0.200591    11.00000   -1.50000
H14C  2    0.153749    0.484816    0.273981    11.00000   -1.50000
AFIX   0
C15   1    0.177771    0.395923   -0.243578    11.00000    0.02753    0.03667 =
         0.02247    0.00143    0.00817   -0.00415
C16   1    0.879203    0.260817    0.337931    11.00000    0.02601    0.03346 =
         0.02612   -0.00505    0.00843    0.00100
HKLF   4
 
REM     NM23 in P 1 21/c 1
REM R1 =  0.0411 for   2238 Fo > 4sig(Fo)  and  0.0499 for all   2649 data
REM    250 parameters refined using      0 restraints
 
END  
     
WGHT      0.0477      0.7789 
REM Highest difference peak  0.398,  deepest hole -0.339,  1-sigma level  0.052
Q1    1   0.9348  0.3268  0.3092  11.00000  0.05    0.40
Q2    1   0.9652  0.2273  0.4864  11.00000  0.05    0.28
Q3    1   0.2038  0.3025 -0.2417  11.00000  0.05    0.24
Q4    1   0.0549  0.4122 -0.2809  11.00000  0.05    0.20
Q5    1   0.2485  0.4972 -0.1015  11.00000  0.05    0.16
;

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
F1A F 0.0796(2) 0.45044(12) -0.33040(17) 0.0669(7) Uani 0.930(4) 1 d P A -1
F2A F 0.25422(16) 0.38258(18) -0.30812(19) 0.0682(8) Uani 0.930(4) 1 d P A -1
F3A F 0.1241(2) 0.31267(14) -0.24063(15) 0.0540(6) Uani 0.930(4) 1 d P A -1
F4A F 0.98971(19) 0.2855(2) 0.4454(2) 0.0606(8) Uani 0.911(5) 1 d P B -1
F5A F 0.88196(17) 0.16645(10) 0.3237(3) 0.0539(7) Uani 0.911(5) 1 d P B -1
F6A F 0.88754(17) 0.29536(17) 0.22174(19) 0.0502(6) Uani 0.911(5) 1 d P B -1
F1B F 0.158(2) 0.4442(14) -0.351(2) 0.043(5) Uani 0.070(4) 1 d P A -2
F2B F 0.2538(19) 0.3205(15) -0.259(2) 0.043(5) Uani 0.070(4) 1 d P A -2
F3B F 0.071(2) 0.3610(18) -0.265(2) 0.043(5) Uani 0.070(4) 1 d P A -2
F4B F 0.967(3) 0.318(2) 0.409(3) 0.062(5) Uani 0.089(5) 1 d P B -2
F5B F 0.9243(16) 0.1835(16) 0.423(3) 0.062(5) Uani 0.089(5) 1 d P B -2
F6B F 0.8711(18) 0.243(2) 0.230(3) 0.062(5) Uani 0.089(5) 1 d P B -2
N1 N 0.30145(13) 0.40617(10) 0.26879(15) 0.0229(3) Uani 1 1 d . . .
O1 O 0.41176(13) 0.36857(10) 0.50019(13) 0.0332(3) Uani 1 1 d . . .
C1 C 0.52991(16) 0.35398(12) 0.36187(18) 0.0203(4) Uani 1 1 d . . .
C2 C 0.65031(17) 0.38792(12) 0.45768(18) 0.0243(4) Uani 1 1 d . . .
H2 H 0.6545 0.4317 0.5286 0.029 Uiso 1 1 calc R . .
C3 C 0.76470(17) 0.35867(12) 0.45113(19) 0.0253(4) Uani 1 1 d . . .
H3 H 0.8469 0.3826 0.5166 0.030 Uiso 1 1 calc R . .
C4 C 0.75793(17) 0.29409(12) 0.34802(18) 0.0226(4) Uani 1 1 d . B .
C5 C 0.63788(17) 0.26063(12) 0.25070(18) 0.0225(4) Uani 1 1 d . . .
H5 H 0.6340 0.2172 0.1795 0.027 Uiso 1 1 calc R . .
C6 C 0.52361(17) 0.29028(12) 0.25692(18) 0.0211(4) Uani 1 1 d . . .
H6 H 0.4413 0.2674 0.1901 0.025 Uiso 1 1 calc R . .
C7 C 0.30891(16) 0.44486(12) 0.14594(18) 0.0206(4) Uani 1 1 d . . .
C8 C 0.24026(16) 0.40200(12) 0.01552(19) 0.0228(4) Uani 1 1 d . . .
H8 H 0.1888 0.3467 0.0072 0.027 Uiso 1 1 calc R . .
C9 C 0.24779(16) 0.44087(12) -0.10225(18) 0.0228(4) Uani 1 1 d . A .
C10 C 0.32124(18) 0.52225(13) -0.09102(19) 0.0269(4) Uani 1 1 d . . .
H10 H 0.3260 0.5484 -0.1723 0.032 Uiso 1 1 calc R . .
C11 C 0.38730(18) 0.56512(13) 0.0386(2) 0.0290(4) Uani 1 1 d . . .
H11 H 0.4367 0.6214 0.0464 0.035 Uiso 1 1 calc R . .
C12 C 0.38199(17) 0.52641(12) 0.15763(19) 0.0246(4) Uani 1 1 d . . .
H12 H 0.4283 0.5557 0.2470 0.030 Uiso 1 1 calc R . .
C13 C 0.40988(17) 0.37834(12) 0.38342(18) 0.0231(4) Uani 1 1 d . . .
C14 C 0.17628(17) 0.41702(14) 0.2788(2) 0.0299(4) Uani 1 1 d . . .
H14A H 0.1842 0.3905 0.3685 0.045 Uiso 1 1 calc R . .
H14B H 0.1075 0.3830 0.2006 0.045 Uiso 1 1 calc R . .
H14C H 0.1537 0.4848 0.2740 0.045 Uiso 1 1 calc R . .
C15 C 0.17777(18) 0.39592(14) -0.2436(2) 0.0298(4) Uani 1 1 d . . .
C16 C 0.87920(19) 0.26082(14) 0.3379(2) 0.0295(4) 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
F1A C15 1.335(2) . ?
F2A C15 1.318(2) . ?
F3A C15 1.322(2) . ?
F4A C16 1.322(3) . ?
F5A C16 1.334(3) . ?
F6A C16 1.351(3) . ?
F1B C15 1.246(19) . ?
F2B C15 1.416(19) . ?
F3B C15 1.23(2) . ?
F4B C16 1.24(3) . ?
F5B C16 1.36(2) . ?
F6B C16 1.13(2) . ?
N1 C13 1.357(2) . ?
N1 C7 1.433(2) . ?
N1 C14 1.470(2) . ?
O1 C13 1.223(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.396(2) . ?
C1 C13 1.506(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 C16 1.493(3) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.385(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 C15 1.490(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 121.89(14) . . ?
C13 N1 C14 119.92(14) . . ?
C7 N1 C14 116.89(14) . . ?
C2 C1 C6 119.72(16) . . ?
C2 C1 C13 118.77(15) . . ?
C6 C1 C13 121.16(15) . . ?
C3 C2 C1 120.67(16) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.32(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.43(16) . . ?
C5 C4 C16 118.76(16) . . ?
C3 C4 C16 120.81(16) . . ?
C6 C5 C4 120.19(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.66(16) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 120.39(16) . . ?
C12 C7 N1 119.64(16) . . ?
C8 C7 N1 119.95(15) . . ?
C9 C8 C7 119.14(16) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.69(16) . . ?
C8 C9 C15 120.79(16) . . ?
C10 C9 C15 118.51(16) . . ?
C11 C10 C9 119.69(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.28(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.81(17) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O1 C13 N1 122.86(16) . . ?
O1 C13 C1 119.51(16) . . ?
N1 C13 C1 117.55(15) . . ?
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 . . ?
F3B C15 F1B 105.2(14) . . ?
F3B C15 F2A 130.8(10) . . ?
F1B C15 F3A 126.3(9) . . ?
F2A C15 F3A 107.09(18) . . ?
F2A C15 F1A 105.48(19) . . ?
F3A C15 F1A 105.43(17) . . ?
F3B C15 F2B 106.0(13) . . ?
F1B C15 F2B 100.8(13) . . ?
F1A C15 F2B 135.8(8) . . ?
F3B C15 C9 114.5(9) . . ?
F1B C15 C9 118.8(8) . . ?
F2A C15 C9 112.64(15) . . ?
F3A C15 C9 113.86(16) . . ?
F1A C15 C9 111.72(17) . . ?
F2B C15 C9 109.9(8) . . ?
F6B C16 F4B 116.8(18) . . ?
F6B C16 F4A 123.9(10) . . ?
F4B C16 F5A 131.0(12) . . ?
F4A C16 F5A 107.28(18) . . ?
F4A C16 F6A 105.7(2) . . ?
F5A C16 F6A 103.94(19) . . ?
F6B C16 F5B 109.2(14) . . ?
F4B C16 F5B 98.1(14) . . ?
F6A C16 F5B 136.8(9) . . ?
F6B C16 C4 117.3(9) . . ?
F4B C16 C4 105.9(12) . . ?
F4A C16 C4 114.76(19) . . ?
F5A C16 C4 112.58(16) . . ?
F6A C16 C4 111.77(16) . . ?
F5B C16 C4 107.5(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.5(3) . . . . ?
C13 C1 C2 C3 172.75(15) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 C16 -179.88(17) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C16 C4 C5 C6 -179.83(16) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C13 C1 C6 C5 -172.26(15) . . . . ?
C13 N1 C7 C12 -58.9(2) . . . . ?
C14 N1 C7 C12 108.01(18) . . . . ?
C13 N1 C7 C8 122.74(18) . . . . ?
C14 N1 C7 C8 -70.3(2) . . . . ?
C12 C7 C8 C9 1.2(2) . . . . ?
N1 C7 C8 C9 179.47(15) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C7 C8 C9 C15 178.78(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C15 C9 C10 C11 -179.83(17) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
N1 C7 C12 C11 -178.71(15) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C7 N1 C13 O1 160.67(17) . . . . ?
C14 N1 C13 O1 -5.9(3) . . . . ?
C7 N1 C13 C1 -22.5(2) . . . . ?
C14 N1 C13 C1 170.90(15) . . . . ?
C2 C1 C13 O1 -47.3(2) . . . . ?
C6 C1 C13 O1 125.85(19) . . . . ?
C2 C1 C13 N1 135.75(17) . . . . ?
C6 C1 C13 N1 -51.1(2) . . . . ?
C8 C9 C15 F3B 35.9(14) . . . . ?
C10 C9 C15 F3B -144.4(14) . . . . ?
C8 C9 C15 F1B 161.4(14) . . . . ?
C10 C9 C15 F1B -18.9(14) . . . . ?
C8 C9 C15 F2A -129.8(2) . . . . ?
C10 C9 C15 F2A 49.9(3) . . . . ?
C8 C9 C15 F3A -7.6(3) . . . . ?
C10 C9 C15 F3A 172.05(19) . . . . ?
C8 C9 C15 F1A 111.7(2) . . . . ?
C10 C9 C15 F1A -68.7(2) . . . . ?
C8 C9 C15 F2B -83.3(11) . . . . ?
C10 C9 C15 F2B 96.4(11) . . . . ?
C5 C4 C16 F6B 30.4(18) . . . . ?
C3 C4 C16 F6B -148.4(17) . . . . ?
C5 C4 C16 F4B 162.9(14) . . . . ?
C3 C4 C16 F4B -15.9(15) . . . . ?
C5 C4 C16 F4A -171.1(2) . . . . ?
C3 C4 C16 F4A 10.0(3) . . . . ?
C5 C4 C16 F5A -48.1(3) . . . . ?
C3 C4 C16 F5A 133.1(2) . . . . ?
C5 C4 C16 F6A 68.5(2) . . . . ?
C3 C4 C16 F6A -110.3(2) . . . . ?
C5 C4 C16 F5B -93.1(12) . . . . ?
C3 C4 C16 F5B 88.1(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_NM31
_database_code_depnum_ccdc_archive 'CCDC 1025684'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N O'
_chemical_formula_sum            'C16 H11 F6 N O'
_chemical_formula_weight         347.26

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                   12.3185(10)
_cell_length_b                   7.9401(5)
_cell_length_c                   15.4912(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.168(4)
_cell_angle_gamma                90.00
_cell_volume                     1515.19(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3569
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      30.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_T_max  0.9771
_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            11173
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2683
_reflns_number_gt                2044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_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)+(0.0354P)²+0.5306P] 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         2683
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL NM31 in P2(1)/c
CELL 0.71073 12.3185 7.9401 15.4912 90.000 90.168 90.000
ZERR 4.00 0.0010 0.0005 0.0012 0.000 0.004 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O F
UNIT 64 44 4 4 24
TEMP -153
ACTA
L.S. 12
SIZE 0.41 0.18 0.16
OMIT -1 50
ACTA
CONF
BOND $H
HTAB
FMAP 2
PLAN 5
BOND $H
CONF
WGHT    0.035400    0.530600
FVAR       0.19243   0.68497
PART -1
F1A   5    0.107605   -0.418016    0.486366    21.00000    0.09574    0.05254 =
         0.10109    0.04032   -0.04496   -0.04628
F2A   5    0.203569   -0.296231    0.576414    21.00000    0.09761    0.03091 =
         0.03311    0.00594   -0.01958    0.00078
F3A   5    0.277988   -0.406083    0.470038    21.00000    0.15890    0.08377 =
         0.08441    0.05559    0.09116    0.09978
PART -2
F1B   5    0.301729   -0.357913    0.495431   -21.00000    0.02798    0.06315 =
         0.15907    0.06012   -0.05348   -0.01218
F2B   5    0.162357   -0.451374    0.451387   -21.00000    0.07160    0.01953 =
         0.05695    0.00128   -0.01763   -0.00953
F3B   5    0.161401   -0.313818    0.566434   -21.00000    0.21239    0.06239 =
         0.06395    0.03750    0.10339    0.07431
PART 0
 
F4    5    0.258060    0.197464    0.105359    11.00000    0.03157    0.04101 =
         0.02719   -0.00318   -0.00876   -0.00792
F5    5    0.365431    0.399520    0.069219    11.00000    0.04769    0.03630 =
         0.02623    0.00848   -0.00813   -0.00512
F6    5    0.419234    0.143484    0.060121    11.00000    0.04559    0.04507 =
         0.02129   -0.00832    0.00110    0.00292
N1    3    0.143421    0.282438    0.297690    11.00000    0.01724    0.02364 =
         0.03318    0.00668   -0.00141    0.00162
O1    4    0.207252    0.493054    0.214213    11.00000    0.02666    0.02337 =
         0.03116    0.00666   -0.00417    0.00161
C1    1    0.338693    0.301912    0.269518    11.00000    0.01892    0.01722 =
         0.02081    0.00075   -0.00125   -0.00273
C2    1    0.404565    0.256469    0.199845    11.00000    0.02345    0.01894 =
         0.01851    0.00023   -0.00027   -0.00288
C3    1    0.512079    0.212051    0.214049    11.00000    0.02195    0.02613 =
         0.02365   -0.00282    0.00429    0.00002
AFIX  43
H3    2    0.556297    0.180193    0.166636    11.00000   -1.20000
AFIX   0
C4    1    0.555674    0.213628    0.296559    11.00000    0.01865    0.02806 =
         0.03038    0.00042   -0.00225    0.00258
AFIX  43
H4    2    0.629602    0.184406    0.305704    11.00000   -1.20000
AFIX   0
C5    1    0.490916    0.257927    0.365233    11.00000    0.02381    0.02899 =
         0.01877    0.00046   -0.00348   -0.00213
AFIX  43
H5    2    0.520333    0.258745    0.421989    11.00000   -1.20000
AFIX   0
C6    1    0.383183    0.301306    0.352140    11.00000    0.02009    0.02475 =
         0.01992   -0.00168    0.00195   -0.00119
AFIX  43
H6    2    0.339244    0.330943    0.400092    11.00000   -1.20000
AFIX   0
C7    1    0.158074    0.131009    0.346168    11.00000    0.01443    0.02151 =
         0.02889    0.00271   -0.00224   -0.00219
C8    1    0.195988   -0.014144    0.306724    11.00000    0.01864    0.02660 =
         0.02373   -0.00169   -0.00159   -0.00435
AFIX  43
H8    2    0.213941   -0.013291    0.247127    11.00000   -1.20000
AFIX   0
C9    1    0.207563   -0.160187    0.354495    11.00000    0.02034    0.02019 =
         0.03103   -0.00427   -0.00108   -0.00094
AFIX  43
H9    2    0.232898   -0.260279    0.327668    11.00000   -1.20000
AFIX   0
C10   1    0.182103   -0.160270    0.441697    11.00000    0.01641    0.02258 =
         0.02803    0.00070   -0.00238   -0.00243
C11   1    0.143599   -0.015602    0.481443    11.00000    0.02271    0.02461 =
         0.02787   -0.00079    0.00408   -0.00227
AFIX  43
H11   2    0.126043   -0.016178    0.541116    11.00000   -1.20000
AFIX   0
C12   1    0.131131    0.129439    0.432990    11.00000    0.02085    0.02068 =
         0.03295   -0.00101    0.00329    0.00093
AFIX  43
H12   2    0.103897    0.228746    0.459401    11.00000   -1.20000
AFIX   0
C13   1    0.224663    0.365555    0.256994    11.00000    0.02261    0.02173 =
         0.01962   -0.00204   -0.00375   -0.00038
C14   1    0.033106    0.351197    0.290769    11.00000    0.01838    0.03592 =
         0.05720    0.01208   -0.00301    0.00511
AFIX 137
H14A  2    0.024192    0.442821    0.332537    11.00000   -1.50000
H14B  2   -0.019777    0.262137    0.302889    11.00000   -1.50000
H14C  2    0.021266    0.394533    0.232260    11.00000   -1.50000
AFIX   0
C15   1    0.196132   -0.318449    0.492493    11.00000    0.03727    0.02318 =
         0.03375   -0.00112   -0.00099   -0.00069
C16   1    0.361679    0.250094    0.109464    11.00000    0.02693    0.02715 =
         0.02593   -0.00119    0.00000   -0.00267
HKLF   4
 
REM  NM31 in P2(1)/c
REM R1 =  0.0384 for   2044 Fo > 4sig(Fo)  and  0.0590 for all   2683 data
REM    246 parameters refined using      0 restraints
 
END  
     
WGHT      0.0354      0.5307 
REM Highest difference peak  0.215,  deepest hole -0.239,  1-sigma level  0.044
Q1    1   0.0395  0.4682  0.2835  11.00000  0.05    0.22
Q2    1   0.2780 -0.3104  0.5601  11.00000  0.05    0.21
Q3    1   0.3883  0.2433  0.1649  11.00000  0.05    0.17
Q4    1   0.2729 -0.4110  0.4159  11.00000  0.05    0.17
Q5    1   0.2777  0.2887  0.2452  11.00000  0.05    0.16
;

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
F1A F 0.1076(6) -0.4180(7) 0.4864(5) 0.083(2) Uani 0.685(12) 1 d P A -1
F2A F 0.2036(4) -0.2962(6) 0.5764(3) 0.0539(14) Uani 0.685(12) 1 d P A -1
F3A F 0.2780(7) -0.4061(8) 0.4700(4) 0.109(3) Uani 0.685(12) 1 d P A -1
F1B F 0.3017(6) -0.3579(12) 0.4954(8) 0.084(4) Uani 0.315(12) 1 d P A -2
F2B F 0.1624(10) -0.4514(6) 0.4514(6) 0.049(2) Uani 0.315(12) 1 d P A -2
F3B F 0.161(2) -0.3138(17) 0.5664(9) 0.113(6) Uani 0.315(12) 1 d P A -2
F4 F 0.25806(9) 0.19746(13) 0.10536(7) 0.0333(3) Uani 1 1 d . . .
F5 F 0.36543(9) 0.39952(13) 0.06922(7) 0.0368(3) Uani 1 1 d . . .
F6 F 0.41923(10) 0.14348(14) 0.06012(7) 0.0373(3) Uani 1 1 d . . .
N1 N 0.14342(12) 0.28244(17) 0.29769(11) 0.0247(4) Uani 1 1 d . . .
O1 O 0.20725(10) 0.49305(14) 0.21421(9) 0.0271(3) Uani 1 1 d . . .
C1 C 0.33869(14) 0.30191(19) 0.26952(12) 0.0190(4) Uani 1 1 d . . .
C2 C 0.40456(14) 0.25647(19) 0.19984(12) 0.0203(4) Uani 1 1 d . . .
C3 C 0.51208(15) 0.2121(2) 0.21405(12) 0.0239(4) Uani 1 1 d . . .
H3 H 0.5563 0.1802 0.1666 0.029 Uiso 1 1 calc R . .
C4 C 0.55567(15) 0.2136(2) 0.29656(13) 0.0257(4) Uani 1 1 d . . .
H4 H 0.6296 0.1844 0.3057 0.031 Uiso 1 1 calc R . .
C5 C 0.49092(15) 0.2579(2) 0.36523(12) 0.0239(4) Uani 1 1 d . . .
H5 H 0.5203 0.2587 0.4220 0.029 Uiso 1 1 calc R . .
C6 C 0.38318(14) 0.3013(2) 0.35214(12) 0.0216(4) Uani 1 1 d . . .
H6 H 0.3392 0.3309 0.4001 0.026 Uiso 1 1 calc R . .
C7 C 0.15807(14) 0.1310(2) 0.34617(12) 0.0216(4) Uani 1 1 d . . .
C8 C 0.19599(14) -0.0141(2) 0.30672(13) 0.0230(4) Uani 1 1 d . . .
H8 H 0.2139 -0.0133 0.2471 0.028 Uiso 1 1 calc R . .
C9 C 0.20756(14) -0.1602(2) 0.35450(13) 0.0239(4) Uani 1 1 d . . .
H9 H 0.2329 -0.2603 0.3277 0.029 Uiso 1 1 calc R . .
C10 C 0.18210(14) -0.1603(2) 0.44170(12) 0.0223(4) Uani 1 1 d . A .
C11 C 0.14360(15) -0.0156(2) 0.48144(13) 0.0251(4) Uani 1 1 d . . .
H11 H 0.1260 -0.0162 0.5411 0.030 Uiso 1 1 calc R . .
C12 C 0.13113(14) 0.1294(2) 0.43299(13) 0.0248(4) Uani 1 1 d . . .
H12 H 0.1039 0.2287 0.4594 0.030 Uiso 1 1 calc R . .
C13 C 0.22466(14) 0.3656(2) 0.25699(12) 0.0213(4) Uani 1 1 d . . .
C14 C 0.03311(15) 0.3512(3) 0.29077(16) 0.0372(5) Uani 1 1 d . . .
H14A H 0.0242 0.4428 0.3325 0.056 Uiso 1 1 calc R . .
H14B H -0.0198 0.2621 0.3029 0.056 Uiso 1 1 calc R . .
H14C H 0.0213 0.3945 0.2323 0.056 Uiso 1 1 calc R . .
C15 C 0.19613(17) -0.3184(2) 0.49249(14) 0.0314(5) Uani 1 1 d . . .
C16 C 0.36168(16) 0.2501(2) 0.10946(13) 0.0267(4) 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
F1A C15 1.350(4) . ?
F2A C15 1.315(5) . ?
F3A C15 1.274(4) . ?
F1B C15 1.339(8) . ?
F2B C15 1.300(6) . ?
F3B C15 1.224(11) . ?
F4 C16 1.344(2) . ?
F5 C16 1.341(2) . ?
F6 C16 1.344(2) . ?
N1 C13 1.356(2) . ?
N1 C7 1.429(2) . ?
N1 C14 1.468(2) . ?
O1 C13 1.229(2) . ?
C1 C6 1.391(3) . ?
C1 C2 1.400(2) . ?
C1 C13 1.505(2) . ?
C2 C3 1.388(2) . ?
C2 C16 1.496(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 C12 1.386(3) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 C15 1.492(3) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 124.18(14) . . ?
C13 N1 C14 117.99(15) . . ?
C7 N1 C14 117.83(15) . . ?
C6 C1 C2 118.75(16) . . ?
C6 C1 C13 119.01(16) . . ?
C2 C1 C13 122.02(16) . . ?
C3 C2 C1 119.90(16) . . ?
C3 C2 C16 118.30(17) . . ?
C1 C2 C16 121.78(16) . . ?
C4 C3 C2 120.76(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.42(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.47(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.68(18) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C12 120.14(16) . . ?
C8 C7 N1 120.68(17) . . ?
C12 C7 N1 119.16(15) . . ?
C9 C8 C7 119.71(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.88(16) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.67(16) . . ?
C11 C10 C15 120.14(18) . . ?
C9 C10 C15 119.19(16) . . ?
C12 C11 C10 119.09(19) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C7 120.50(16) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
O1 C13 N1 121.60(16) . . ?
O1 C13 C1 120.51(16) . . ?
N1 C13 C1 117.81(15) . . ?
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 . . ?
F3B C15 F3A 123.4(8) . . ?
F3B C15 F2B 111.7(8) . . ?
F3A C15 F2A 106.9(4) . . ?
F2B C15 F2A 127.9(5) . . ?
F3B C15 F1B 108.5(10) . . ?
F3A C15 F1A 107.5(3) . . ?
F2A C15 F1A 101.7(4) . . ?
F1B C15 F1A 130.5(4) . . ?
F3B C15 C10 115.3(6) . . ?
F3A C15 C10 114.0(2) . . ?
F2B C15 C10 112.9(3) . . ?
F2A C15 C10 114.6(3) . . ?
F1B C15 C10 109.0(4) . . ?
F1A C15 C10 111.3(2) . . ?
F5 C16 F6 105.89(15) . . ?
F5 C16 F4 106.68(15) . . ?
F6 C16 F4 106.24(14) . . ?
F5 C16 C2 113.12(14) . . ?
F6 C16 C2 111.60(15) . . ?
F4 C16 C2 112.80(16) . . ?

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 0.0(2) . . . . ?
C13 C1 C2 C3 174.56(15) . . . . ?
C6 C1 C2 C16 178.47(15) . . . . ?
C13 C1 C2 C16 -6.9(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C16 C2 C3 C4 -179.19(15) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C13 C1 C6 C5 -174.22(15) . . . . ?
C13 N1 C7 C8 -61.7(2) . . . . ?
C14 N1 C7 C8 117.6(2) . . . . ?
C13 N1 C7 C12 119.97(19) . . . . ?
C14 N1 C7 C12 -60.7(2) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
N1 C7 C8 C9 -178.74(15) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C8 C9 C10 C15 -179.38(17) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C15 C10 C11 C12 -179.91(16) . . . . ?
C10 C11 C12 C7 -0.9(3) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
N1 C7 C12 C11 179.49(16) . . . . ?
C7 N1 C13 O1 178.07(16) . . . . ?
C14 N1 C13 O1 -1.2(3) . . . . ?
C7 N1 C13 C1 -5.1(3) . . . . ?
C14 N1 C13 C1 175.66(16) . . . . ?
C6 C1 C13 O1 115.20(19) . . . . ?
C2 C1 C13 O1 -59.4(2) . . . . ?
C6 C1 C13 N1 -61.7(2) . . . . ?
C2 C1 C13 N1 123.70(18) . . . . ?
C11 C10 C15 F3B 7.1(15) . . . . ?
C9 C10 C15 F3B -172.6(15) . . . . ?
C11 C10 C15 F3A -144.2(6) . . . . ?
C9 C10 C15 F3A 36.1(6) . . . . ?
C11 C10 C15 F2B 137.2(7) . . . . ?
C9 C10 C15 F2B -42.5(7) . . . . ?
C11 C10 C15 F2A -20.6(4) . . . . ?
C9 C10 C15 F2A 159.6(3) . . . . ?
C11 C10 C15 F1B -115.2(6) . . . . ?
C9 C10 C15 F1B 65.0(6) . . . . ?
C11 C10 C15 F1A 94.0(5) . . . . ?
C9 C10 C15 F1A -85.7(5) . . . . ?
C3 C2 C16 F5 -95.55(19) . . . . ?
C1 C2 C16 F5 85.9(2) . . . . ?
C3 C2 C16 F6 23.7(2) . . . . ?
C1 C2 C16 F6 -154.78(15) . . . . ?
C3 C2 C16 F4 143.26(15) . . . . ?
C1 C2 C16 F4 -35.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_NM33
_database_code_depnum_ccdc_archive 'CCDC 1025685'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-13
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N O'
_chemical_formula_sum            'C16 H11 F6 N O'
_chemical_formula_weight         347.26

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           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9977(4)
_cell_length_b                   10.8088(5)
_cell_length_c                   16.6720(9)
_cell_angle_alpha                105.291(2)
_cell_angle_beta                 98.901(2)
_cell_angle_gamma                102.688(2)
_cell_volume                     1486.36(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4159
_cell_measurement_theta_min      2.3708
_cell_measurement_theta_max      29.3038

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9409
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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            30219
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         30.67
_reflns_number_total             9103
_reflns_number_gt                7006
_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          
; 
 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. 
;

_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)+(0.0495P)²+0.6094P] 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         9103
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL NM-3-3 in P-1
CELL 0.71073 8.9977 10.8088 16.6720 105.291 98.901 102.688
ZERR 4.00 0.0004 0.0005 0.0009 0.002 0.002 0.002
LATT 1
SFAC C H N O F
UNIT 64 44 4 4 24
TEMP -153
ACTA
BOND $H
CONF
HTAB
L.S. 12
SIZE 0.2 0.15 0.1
FMAP 2
PLAN 5
BOND $H
WGHT    0.049500    0.609400
FVAR       0.21780   0.53697   0.58478
F1    5    0.336366    0.237305   -0.454014    11.00000    0.03544    0.06455 =
         0.01883    0.01215    0.00869   -0.01159
F2    5    0.194462    0.041847   -0.470574    11.00000    0.07494    0.03668 =
         0.02398    0.00020    0.01998    0.01175
F3    5    0.087319    0.194403   -0.483295    11.00000    0.04047    0.08158 =
         0.02073    0.02040   -0.00172    0.01968
F4    5    0.717787   -0.107926   -0.092601    11.00000    0.03463    0.01862 =
         0.04661    0.00873    0.01153    0.01317
F5    5    0.863526    0.036186    0.023081    11.00000    0.02933    0.04736 =
         0.02859    0.01519    0.00700    0.02497
F6    5    0.880125    0.066747   -0.097635    11.00000    0.03569    0.03420 =
         0.04404    0.02281    0.02828    0.02074
N1    3    0.207807    0.316815   -0.082551    11.00000    0.01507    0.02539 =
         0.01342    0.00249    0.00375    0.00945
O1    4    0.344021    0.401146    0.054619    11.00000    0.02312    0.02370 =
         0.01391    0.00161    0.00399    0.00993
C1    1    0.443260    0.248027   -0.036092    11.00000    0.01579    0.01714 =
         0.01220    0.00466    0.00412    0.00554
C2    1    0.593659    0.300033    0.016214    11.00000    0.01823    0.01628 =
         0.01540    0.00087    0.00147    0.00477
AFIX  43
H2    2    0.622295    0.386954    0.056109    11.00000   -1.20000
AFIX   0
C3    1    0.701354    0.226168    0.010483    11.00000    0.01566    0.01984 =
         0.01881    0.00502    0.00254    0.00557
AFIX  43
H3    2    0.804169    0.262476    0.045439    11.00000   -1.20000
AFIX   0
C4    1    0.657256    0.097996   -0.047120    11.00000    0.01986    0.01795 =
         0.01599    0.00812    0.00749    0.00816
C5    1    0.507600    0.043862   -0.098611    11.00000    0.02095    0.01427 =
         0.01526    0.00440    0.00567    0.00484
AFIX  43
H5    2    0.478298   -0.044200   -0.137097    11.00000   -1.20000
AFIX   0
C6    1    0.400800    0.119535   -0.093441    11.00000    0.01666    0.01740 =
         0.01365    0.00490    0.00293    0.00341
AFIX  43
H6    2    0.298577    0.083539   -0.129110    11.00000   -1.20000
AFIX   0
C7    1    0.210112    0.278412   -0.171319    11.00000    0.01514    0.01934 =
         0.01339    0.00486    0.00339    0.00770
C8    1    0.338117    0.336983   -0.198521    11.00000    0.01465    0.01608 =
         0.01559    0.00361    0.00141    0.00421
AFIX  43
H8    2    0.425583    0.401063   -0.158179    11.00000   -1.20000
AFIX   0
C9    1    0.337969    0.301565   -0.285081    11.00000    0.01635    0.01877 =
         0.01755    0.00733    0.00451    0.00440
AFIX  43
H9    2    0.426041    0.340507   -0.303838    11.00000   -1.20000
AFIX   0
C10   1    0.209519    0.209627   -0.343798    11.00000    0.01870    0.02101 =
         0.01341    0.00640    0.00243    0.00520
C11   1    0.079976    0.151640   -0.316799    11.00000    0.01590    0.02626 =
         0.01646    0.00425    0.00054    0.00135
AFIX  43
H11   2   -0.008141    0.088806   -0.357364    11.00000   -1.20000
AFIX   0
C12   1    0.080182    0.185963   -0.230601    11.00000    0.01465    0.02685 =
         0.01721    0.00612    0.00305    0.00246
AFIX  43
H12   2   -0.007796    0.146722   -0.211893    11.00000   -1.20000
AFIX   0
C13   1    0.330009    0.329745   -0.018603    11.00000    0.01586    0.01662 =
         0.01412    0.00423    0.00414    0.00484
C14   1    0.085014    0.379192   -0.058552    11.00000    0.01797    0.03153 =
         0.02376    0.00287    0.00665    0.01259
AFIX 137
H14A  2    0.074728    0.377158   -0.001215    11.00000   -1.50000
H14B  2   -0.014557    0.330163   -0.099462    11.00000   -1.50000
H14C  2    0.112939    0.471877   -0.058964    11.00000   -1.50000
AFIX   0
C15   1    0.207424    0.171285   -0.437241    11.00000    0.02414    0.03311 =
         0.01573    0.00784    0.00332    0.00165
C16   1    0.777906    0.022330   -0.053627    11.00000    0.02333    0.02060 =
         0.02246    0.00973    0.01007    0.00960
PART -1
F1A'  5    0.796572    0.295426    0.442896    21.00000    0.03408    0.06283 =
         0.05885    0.04282    0.00128    0.01717
F2A'  5    0.837957    0.504062    0.474884    21.00000    0.02595    0.04097 =
         0.07178   -0.02576   -0.00770    0.01093
F3A'  5    0.877248    0.400522    0.358615    21.00000    0.03148    0.09442 =
         0.03119    0.02177    0.01959    0.03591
 
F4A'  5    0.560171    0.999500    0.312920    31.00000    0.03593    0.02632 =
         0.06012    0.00894    0.01575   -0.00353
F6A'  5    0.340961    1.036061    0.291275    31.00000    0.05384    0.02018 =
         0.05605    0.01490   -0.00919    0.01091
F5A'  5    0.449860    1.037582    0.418580    31.00000    0.08988    0.01784 =
         0.03127   -0.00470    0.03200    0.00024
PART -2
F1B'  5    0.807796    0.281395    0.417946   -21.00000    0.03948    0.03747 =
         0.17282    0.03155   -0.01594    0.01862
F2B'  5    0.831586    0.484201    0.483187   -21.00000    0.02362    0.08399 =
         0.01558    0.00697    0.00240    0.01408
F3B'  5    0.878740    0.426380    0.359514   -21.00000    0.01927    0.15156 =
         0.04691    0.03968    0.00993    0.00290
 
F4B'  5    0.515040    1.018139    0.300560   -31.00000    0.13880    0.03095 =
         0.04398   -0.00496    0.05754   -0.02859
F5B'  5    0.472107    1.031354    0.419547   -31.00000    0.06713    0.03102 =
         0.02853   -0.00334   -0.01040   -0.01696
F6B'  5    0.296703    1.040368    0.330395   -31.00000    0.04611    0.01912 =
         0.14904    0.01460   -0.02099    0.01005
PART 0
N1'   3    0.144628    0.329736    0.261372    11.00000    0.02042    0.01417 =
         0.02213    0.00456    0.00157    0.00206
O1'   4   -0.030367    0.388220    0.175822    11.00000    0.03407    0.02573 =
         0.03526    0.00736   -0.01670   -0.00056
C1'   1    0.194636    0.559714    0.257958    11.00000    0.01773    0.01666 =
         0.01759    0.00428   -0.00128    0.00520
C2'   1    0.246247    0.620355    0.199681    11.00000    0.01756    0.01972 =
         0.01493    0.00201    0.00104    0.00794
AFIX  43
H2'   2    0.230157    0.569230    0.141627    11.00000   -1.20000
AFIX   0
C3'   1    0.321016    0.755174    0.226370    11.00000    0.01786    0.02109 =
         0.01787    0.00742    0.00380    0.00608
AFIX  43
H3'   2    0.357328    0.796708    0.186781    11.00000   -1.20000
AFIX   0
C4'   1    0.343134    0.830187    0.311374    11.00000    0.01958    0.01517 =
         0.01958    0.00385    0.00227    0.00542
C5'   1    0.293368    0.770494    0.370312    11.00000    0.02723    0.01862 =
         0.01436    0.00189    0.00202    0.00532
AFIX  43
H5'   2    0.309412    0.821901    0.428300    11.00000   -1.20000
AFIX   0
C6'   1    0.219731    0.634501    0.343423    11.00000    0.02772    0.01990 =
         0.01609    0.00658    0.00239    0.00336
AFIX  43
H6'   2    0.186395    0.592363    0.383361    11.00000   -1.20000
AFIX   0
C7'   1    0.305716    0.348753    0.298439    11.00000    0.02101    0.01211 =
         0.01755    0.00368    0.00363    0.00416
C8'   1    0.416858    0.363187    0.249856    11.00000    0.02810    0.01878 =
         0.01566    0.00618    0.00605    0.00748
AFIX  43
H8'   2    0.386614    0.363540    0.192756    11.00000   -1.20000
AFIX   0
C9'   1    0.572047    0.377081    0.284876    11.00000    0.02515    0.02035 =
         0.02092    0.00763    0.00999    0.00817
AFIX  43
H9'   2    0.648592    0.387538    0.252015    11.00000   -1.20000
AFIX   0
C10'  1    0.615026    0.375635    0.368210    11.00000    0.02182    0.01791 =
         0.02020    0.00554    0.00590    0.00711
C11'  1    0.503498    0.360053    0.416663    11.00000    0.02383    0.02120 =
         0.01617    0.00615    0.00486    0.00649
AFIX  43
H11'  2    0.533527    0.358735    0.473559    11.00000   -1.20000
AFIX   0
C12'  1    0.349100    0.346516    0.381796    11.00000    0.02194    0.01901 =
         0.01881    0.00638    0.00759    0.00475
AFIX  43
H12'  2    0.272563    0.335692    0.414624    11.00000   -1.20000
AFIX   0
C13'  1    0.095106    0.417936    0.226683    11.00000    0.02514    0.01739 =
         0.01897    0.00319   -0.00133    0.00284
C14'  1    0.038155    0.196361    0.242639    11.00000    0.02479    0.01531 =
         0.03596    0.00441    0.00226    0.00007
AFIX 137
H14D  2   -0.070312    0.200945    0.230951    11.00000   -1.50000
H14E  2    0.057061    0.163882    0.291855    11.00000   -1.50000
H14F  2    0.056669    0.135255    0.192612    11.00000   -1.50000
AFIX   0
C15'  1    0.781661    0.392454    0.408443    11.00000    0.02316    0.03088 =
         0.02746    0.00769    0.00757    0.01039
C16'  1    0.417066    0.976676    0.336933    11.00000    0.03486    0.01880 =
         0.02696    0.00665   -0.00138    0.00364
HKLF   4
 
REM  NM-3-3 in P-1
REM R1 =  0.0430 for   7006 Fo > 4sig(Fo)  and  0.0602 for all   9103 data
REM    491 parameters refined using      0 restraints
 
END  
     
WGHT      0.0495      0.6098 
REM Highest difference peak  0.446,  deepest hole -0.380,  1-sigma level  0.053
Q1    1   0.7143  0.0597 -0.0502  11.00000  0.05    0.45
Q2    1   0.3780  0.9012  0.3258  11.00000  0.05    0.43
Q3    1   0.3845  0.2804 -0.0307  11.00000  0.05    0.40
Q4    1   0.2088  0.1923 -0.3889  11.00000  0.05    0.38
Q5    1   0.3314  0.3607  0.3425  11.00000  0.05    0.35
;

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 0.33637(11) 0.23731(11) -0.45401(5) 0.0437(3) Uani 1 1 d . . .
F2 F 0.19446(14) 0.04185(10) -0.47057(6) 0.0466(3) Uani 1 1 d . . .
F3 F 0.08732(12) 0.19440(13) -0.48329(6) 0.0472(3) Uani 1 1 d . . .
F4 F 0.71779(11) -0.10793(8) -0.09260(6) 0.0323(2) Uani 1 1 d . . .
F5 F 0.86353(10) 0.03619(10) 0.02308(5) 0.0319(2) Uani 1 1 d . . .
F6 F 0.88012(10) 0.06675(9) -0.09764(6) 0.0317(2) Uani 1 1 d . . .
N1 N 0.20781(12) 0.31681(11) -0.08255(6) 0.0180(2) Uani 1 1 d . . .
O1 O 0.34402(11) 0.40115(9) 0.05462(5) 0.02053(19) Uani 1 1 d . . .
C1 C 0.44326(13) 0.24803(12) -0.03609(7) 0.0147(2) Uani 1 1 d . . .
C2 C 0.59366(14) 0.30003(12) 0.01621(8) 0.0177(2) Uani 1 1 d . . .
H2 H 0.6223 0.3870 0.0561 0.021 Uiso 1 1 calc R . .
C3 C 0.70135(14) 0.22617(13) 0.01048(8) 0.0183(2) Uani 1 1 d . . .
H3 H 0.8042 0.2625 0.0454 0.022 Uiso 1 1 calc R . .
C4 C 0.65726(14) 0.09800(12) -0.04712(7) 0.0165(2) Uani 1 1 d . . .
C5 C 0.50760(14) 0.04386(12) -0.09861(7) 0.0167(2) Uani 1 1 d . . .
H5 H 0.4783 -0.0442 -0.1371 0.020 Uiso 1 1 calc R . .
C6 C 0.40080(14) 0.11953(12) -0.09344(7) 0.0161(2) Uani 1 1 d . . .
H6 H 0.2986 0.0835 -0.1291 0.019 Uiso 1 1 calc R . .
C7 C 0.21011(14) 0.27841(12) -0.17132(7) 0.0155(2) Uani 1 1 d . . .
C8 C 0.33812(14) 0.33698(12) -0.19852(7) 0.0159(2) Uani 1 1 d . . .
H8 H 0.4256 0.4011 -0.1582 0.019 Uiso 1 1 calc R . .
C9 C 0.33797(14) 0.30157(12) -0.28508(8) 0.0172(2) Uani 1 1 d . . .
H9 H 0.4260 0.3405 -0.3038 0.021 Uiso 1 1 calc R . .
C10 C 0.20952(14) 0.20963(13) -0.34380(7) 0.0177(2) Uani 1 1 d . . .
C11 C 0.07998(15) 0.15164(14) -0.31680(8) 0.0211(2) Uani 1 1 d . . .
H11 H -0.0081 0.0888 -0.3574 0.025 Uiso 1 1 calc R . .
C12 C 0.08018(14) 0.18596(13) -0.23060(8) 0.0203(2) Uani 1 1 d . . .
H12 H -0.0078 0.1467 -0.2119 0.024 Uiso 1 1 calc R . .
C13 C 0.33001(14) 0.32975(12) -0.01860(7) 0.0155(2) Uani 1 1 d . . .
C14 C 0.08501(15) 0.37919(15) -0.05855(9) 0.0244(3) Uani 1 1 d . . .
H14A H 0.0747 0.3772 -0.0012 0.037 Uiso 1 1 calc R . .
H14B H -0.0146 0.3302 -0.0995 0.037 Uiso 1 1 calc R . .
H14C H 0.1129 0.4719 -0.0590 0.037 Uiso 1 1 calc R . .
C15 C 0.20742(16) 0.17128(15) -0.43724(8) 0.0254(3) Uani 1 1 d . . .
C16 C 0.77791(15) 0.02233(13) -0.05363(8) 0.0203(2) Uani 1 1 d . . .
F1A' F 0.7966(9) 0.2954(8) 0.4429(4) 0.0475(14) Uani 0.54(3) 1 d P A -1
F2A' F 0.8380(9) 0.5041(9) 0.4749(5) 0.0568(16) Uani 0.54(3) 1 d P A -1
F3A' F 0.8772(10) 0.4005(11) 0.3586(5) 0.0473(14) Uani 0.54(3) 1 d P A -1
F4A' F 0.5602(5) 0.9995(5) 0.3129(3) 0.0431(9) Uani 0.58(2) 1 d P B -1
F6A' F 0.3410(8) 1.0361(3) 0.2913(3) 0.0451(13) Uani 0.58(2) 1 d P B -1
F5A' F 0.4499(12) 1.0376(9) 0.4186(5) 0.0491(17) Uani 0.58(2) 1 d P B -1
F1B' F 0.8078(12) 0.2814(10) 0.4179(14) 0.087(3) Uani 0.46(3) 1 d P A -2
F2B' F 0.8316(10) 0.4842(10) 0.4832(4) 0.0431(17) Uani 0.46(3) 1 d P A -2
F3B' F 0.8787(12) 0.4264(18) 0.3595(7) 0.074(3) Uani 0.46(3) 1 d P A -2
F4B' F 0.515(2) 1.0181(9) 0.3006(6) 0.079(4) Uani 0.42(2) 1 d P B -2
F5B' F 0.4721(16) 1.0314(14) 0.4195(7) 0.052(3) Uani 0.42(2) 1 d P B -2
F6B' F 0.2967(9) 1.0404(4) 0.3304(14) 0.078(4) Uani 0.42(2) 1 d P B -2
N1' N 0.14463(13) 0.32974(10) 0.26137(7) 0.0199(2) Uani 1 1 d . . .
O1' O -0.03037(13) 0.38822(11) 0.17582(7) 0.0364(3) Uani 1 1 d . . .
C1' C 0.19464(14) 0.55971(12) 0.25796(8) 0.0181(2) Uani 1 1 d . . .
C2' C 0.24625(14) 0.62036(12) 0.19968(8) 0.0179(2) Uani 1 1 d . . .
H2' H 0.2302 0.5692 0.1416 0.021 Uiso 1 1 calc R . .
C3' C 0.32102(14) 0.75517(13) 0.22637(8) 0.0186(2) Uani 1 1 d . . .
H3' H 0.3573 0.7967 0.1868 0.022 Uiso 1 1 calc R . .
C4' C 0.34313(15) 0.83019(12) 0.31137(8) 0.0186(2) Uani 1 1 d . B .
C5' C 0.29337(16) 0.77049(13) 0.37031(8) 0.0212(2) Uani 1 1 d . . .
H5' H 0.3094 0.8219 0.4283 0.025 Uiso 1 1 calc R . .
C6' C 0.21973(16) 0.63450(13) 0.34342(8) 0.0218(3) Uani 1 1 d . . .
H6' H 0.1864 0.5924 0.3834 0.026 Uiso 1 1 calc R . .
C7' C 0.30572(15) 0.34875(12) 0.29844(8) 0.0172(2) Uani 1 1 d . . .
C8' C 0.41686(16) 0.36319(13) 0.24986(8) 0.0204(2) Uani 1 1 d . . .
H8' H 0.3866 0.3635 0.1928 0.024 Uiso 1 1 calc R . .
C9' C 0.57205(16) 0.37708(13) 0.28488(8) 0.0210(2) Uani 1 1 d . . .
H9' H 0.6486 0.3875 0.2520 0.025 Uiso 1 1 calc R . .
C10' C 0.61503(15) 0.37563(13) 0.36821(8) 0.0196(2) Uani 1 1 d . A .
C11' C 0.50350(15) 0.36005(13) 0.41666(8) 0.0202(2) Uani 1 1 d . . .
H11' H 0.5335 0.3587 0.4736 0.024 Uiso 1 1 calc R . .
C12' C 0.34910(15) 0.34652(13) 0.38180(8) 0.0196(2) Uani 1 1 d . . .
H12' H 0.2726 0.3357 0.4146 0.024 Uiso 1 1 calc R . .
C13' C 0.09511(16) 0.41794(13) 0.22668(8) 0.0222(3) Uani 1 1 d . . .
C14' C 0.03816(17) 0.19636(13) 0.24264(10) 0.0275(3) Uani 1 1 d . . .
H14D H -0.0703 0.2009 0.2310 0.041 Uiso 1 1 calc R . .
H14E H 0.0571 0.1639 0.2919 0.041 Uiso 1 1 calc R . .
H14F H 0.0567 0.1353 0.1926 0.041 Uiso 1 1 calc R . .
C15' C 0.78166(17) 0.39245(15) 0.40844(9) 0.0267(3) Uani 1 1 d . . .
C16' C 0.41707(18) 0.97668(14) 0.33693(9) 0.0285(3) 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 1.3324(16) . ?
F2 C15 1.3334(18) . ?
F3 C15 1.3352(17) . ?
F4 C16 1.3309(15) . ?
F5 C16 1.3397(15) . ?
F6 C16 1.3474(14) . ?
N1 C13 1.3625(15) . ?
N1 C7 1.4326(15) . ?
N1 C14 1.4687(16) . ?
O1 C13 1.2306(14) . ?
C1 C6 1.3937(16) . ?
C1 C2 1.3964(17) . ?
C1 C13 1.5017(16) . ?
C2 C3 1.3834(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3921(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3870(17) . ?
C4 C16 1.4963(17) . ?
C5 C6 1.3905(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3877(16) . ?
C7 C12 1.3966(17) . ?
C8 C9 1.3917(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3834(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3944(17) . ?
C10 C15 1.4987(17) . ?
C11 C12 1.3858(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
F1A' C15' 1.343(6) . ?
F2A' C15' 1.339(6) . ?
F3A' C15' 1.290(8) . ?
F4A' C16' 1.397(5) . ?
F6A' C16' 1.323(3) . ?
F5A' C16' 1.300(7) . ?
F1B' C15' 1.317(9) . ?
F2B' C15' 1.310(7) . ?
F3B' C15' 1.342(12) . ?
F4B' C16' 1.217(8) . ?
F5B' C16' 1.312(10) . ?
F6B' C16' 1.410(6) . ?
N1' C13' 1.3563(17) . ?
N1' C7' 1.4318(16) . ?
N1' C14' 1.4686(17) . ?
O1' C13' 1.2238(16) . ?
C1' C2' 1.3896(18) . ?
C1' C6' 1.3955(17) . ?
C1' C13' 1.5011(18) . ?
C2' C3' 1.3816(18) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.3933(17) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.3878(18) . ?
C4' C16' 1.4916(18) . ?
C5' C6' 1.3904(18) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C8' 1.3890(17) . ?
C7' C12' 1.3922(17) . ?
C8' C9' 1.3866(19) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.3885(18) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.3915(17) . ?
C10' C15' 1.4952(19) . ?
C11' C12' 1.3803(18) . ?
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 124.08(10) . . ?
C13 N1 C14 117.15(10) . . ?
C7 N1 C14 116.72(10) . . ?
C6 C1 C2 119.51(11) . . ?
C6 C1 C13 123.56(11) . . ?
C2 C1 C13 116.48(10) . . ?
C3 C2 C1 120.62(11) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.20(11) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.98(11) . . ?
C5 C4 C16 121.13(11) . . ?
C3 C4 C16 117.86(11) . . ?
C4 C5 C6 119.46(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.21(11) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 120.24(11) . . ?
C8 C7 N1 120.10(11) . . ?
C12 C7 N1 119.61(11) . . ?
C7 C8 C9 119.80(11) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.97(11) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.39(11) . . ?
C9 C10 C15 120.51(11) . . ?
C11 C10 C15 119.10(11) . . ?
C12 C11 C10 119.79(11) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 119.80(11) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
O1 C13 N1 121.15(11) . . ?
O1 C13 C1 119.16(11) . . ?
N1 C13 C1 119.54(10) . . ?
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 . . ?
F1 C15 F2 106.59(12) . . ?
F1 C15 F3 106.36(12) . . ?
F2 C15 F3 105.51(12) . . ?
F1 C15 C10 112.62(11) . . ?
F2 C15 C10 112.54(12) . . ?
F3 C15 C10 112.68(12) . . ?
F4 C16 F5 106.87(11) . . ?
F4 C16 F6 106.67(10) . . ?
F5 C16 F6 105.98(11) . . ?
F4 C16 C4 113.46(11) . . ?
F5 C16 C4 112.16(10) . . ?
F6 C16 C4 111.24(10) . . ?
C13' N1' C7' 122.46(11) . . ?
C13' N1' C14' 118.68(11) . . ?
C7' N1' C14' 117.23(11) . . ?
C2' C1' C6' 120.09(11) . . ?
C2' C1' C13' 119.53(11) . . ?
C6' C1' C13' 119.96(11) . . ?
C3' C2' C1' 119.84(11) . . ?
C3' C2' H2' 120.1 . . ?
C1' C2' H2' 120.1 . . ?
C2' C3' C4' 119.97(12) . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C5' C4' C3' 120.70(12) . . ?
C5' C4' C16' 120.81(12) . . ?
C3' C4' C16' 118.47(12) . . ?
C4' C5' C6' 119.17(11) . . ?
C4' C5' H5' 120.4 . . ?
C6' C5' H5' 120.4 . . ?
C5' C6' C1' 120.21(12) . . ?
C5' C6' H6' 119.9 . . ?
C1' C6' H6' 119.9 . . ?
C8' C7' C12' 120.30(12) . . ?
C8' C7' N1' 119.88(11) . . ?
C12' C7' N1' 119.76(11) . . ?
C9' C8' C7' 119.86(12) . . ?
C9' C8' H8' 120.1 . . ?
C7' C8' H8' 120.1 . . ?
C8' C9' C10' 119.67(12) . . ?
C8' C9' H9' 120.2 . . ?
C10' C9' H9' 120.2 . . ?
C9' C10' C11' 120.49(12) . . ?
C9' C10' C15' 121.10(12) . . ?
C11' C10' C15' 118.41(12) . . ?
C12' C11' C10' 119.79(12) . . ?
C12' C11' H11' 120.1 . . ?
C10' C11' H11' 120.1 . . ?
C11' C12' C7' 119.89(11) . . ?
C11' C12' H12' 120.1 . . ?
C7' C12' H12' 120.1 . . ?
O1' C13' N1' 122.71(12) . . ?
O1' C13' C1' 119.58(12) . . ?
N1' C13' C1' 117.54(11) . . ?
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 . . ?
F3A' C15' F2B' 113.6(6) . . ?
F3A' C15' F1B' 92.3(9) . . ?
F2B' C15' F1B' 107.7(8) . . ?
F3A' C15' F2A' 105.5(6) . . ?
F1B' C15' F2A' 118.3(6) . . ?
F2B' C15' F3B' 106.7(7) . . ?
F1B' C15' F3B' 103.7(7) . . ?
F2A' C15' F3B' 97.2(6) . . ?
F3A' C15' F1A' 108.9(5) . . ?
F2B' C15' F1A' 92.0(5) . . ?
F2A' C15' F1A' 103.6(5) . . ?
F3B' C15' F1A' 119.5(7) . . ?
F3A' C15' C10' 114.9(4) . . ?
F2B' C15' C10' 113.3(4) . . ?
F1B' C15' C10' 113.0(4) . . ?
F2A' C15' C10' 111.3(4) . . ?
F3B' C15' C10' 111.8(5) . . ?
F1A' C15' C10' 111.8(3) . . ?
F4B' C16' F5A' 113.9(6) . . ?
F4B' C16' F5B' 108.5(8) . . ?
F5A' C16' F6A' 113.2(5) . . ?
F5B' C16' F6A' 121.2(7) . . ?
F5A' C16' F4A' 105.2(5) . . ?
F5B' C16' F4A' 97.3(7) . . ?
F6A' C16' F4A' 100.5(4) . . ?
F4B' C16' F6B' 109.4(5) . . ?
F5A' C16' F6B' 86.8(8) . . ?
F5B' C16' F6B' 96.4(9) . . ?
F4A' C16' F6B' 130.6(7) . . ?
F4B' C16' C4' 118.7(5) . . ?
F5A' C16' C4' 114.9(4) . . ?
F5B' C16' C4' 113.4(7) . . ?
F6A' C16' C4' 112.34(18) . . ?
F4A' C16' C4' 109.3(2) . . ?
F6B' C16' C4' 108.0(2) . . ?

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 1.17(18) . . . . ?
C13 C1 C2 C3 173.69(11) . . . . ?
C1 C2 C3 C4 -1.14(18) . . . . ?
C2 C3 C4 C5 0.09(18) . . . . ?
C2 C3 C4 C16 178.19(11) . . . . ?
C3 C4 C5 C6 0.93(18) . . . . ?
C16 C4 C5 C6 -177.11(11) . . . . ?
C4 C5 C6 C1 -0.90(17) . . . . ?
C2 C1 C6 C5 -0.13(17) . . . . ?
C13 C1 C6 C5 -172.09(11) . . . . ?
C13 N1 C7 C8 -46.04(18) . . . . ?
C14 N1 C7 C8 117.18(13) . . . . ?
C13 N1 C7 C12 136.65(13) . . . . ?
C14 N1 C7 C12 -60.13(16) . . . . ?
C12 C7 C8 C9 -1.16(18) . . . . ?
N1 C7 C8 C9 -178.45(11) . . . . ?
C7 C8 C9 C10 0.92(18) . . . . ?
C8 C9 C10 C11 -0.22(19) . . . . ?
C8 C9 C10 C15 179.60(12) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C15 C10 C11 C12 179.94(13) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C8 C7 C12 C11 0.70(19) . . . . ?
N1 C7 C12 C11 178.00(12) . . . . ?
C7 N1 C13 O1 156.45(12) . . . . ?
C14 N1 C13 O1 -6.70(18) . . . . ?
C7 N1 C13 C1 -28.03(18) . . . . ?
C14 N1 C13 C1 168.81(11) . . . . ?
C6 C1 C13 O1 142.44(12) . . . . ?
C2 C1 C13 O1 -29.74(16) . . . . ?
C6 C1 C13 N1 -33.16(17) . . . . ?
C2 C1 C13 N1 154.65(11) . . . . ?
C9 C10 C15 F1 -1.79(19) . . . . ?
C11 C10 C15 F1 178.03(13) . . . . ?
C9 C10 C15 F2 118.73(14) . . . . ?
C11 C10 C15 F2 -61.45(17) . . . . ?
C9 C10 C15 F3 -122.11(14) . . . . ?
C11 C10 C15 F3 57.71(17) . . . . ?
C5 C4 C16 F4 -18.10(16) . . . . ?
C3 C4 C16 F4 163.81(11) . . . . ?
C5 C4 C16 F5 -139.32(12) . . . . ?
C3 C4 C16 F5 42.58(15) . . . . ?
C5 C4 C16 F6 102.18(14) . . . . ?
C3 C4 C16 F6 -75.92(14) . . . . ?
C6' C1' C2' C3' -0.68(19) . . . . ?
C13' C1' C2' C3' 171.91(11) . . . . ?
C1' C2' C3' C4' -0.62(18) . . . . ?
C2' C3' C4' C5' 1.21(19) . . . . ?
C2' C3' C4' C16' -176.95(12) . . . . ?
C3' C4' C5' C6' -0.5(2) . . . . ?
C16' C4' C5' C6' 177.64(13) . . . . ?
C4' C5' C6' C1' -0.8(2) . . . . ?
C2' C1' C6' C5' 1.4(2) . . . . ?
C13' C1' C6' C5' -171.16(12) . . . . ?
C13' N1' C7' C8' -57.41(17) . . . . ?
C14' N1' C7' C8' 107.86(14) . . . . ?
C13' N1' C7' C12' 125.55(13) . . . . ?
C14' N1' C7' C12' -69.18(15) . . . . ?
C12' C7' C8' C9' -0.80(19) . . . . ?
N1' C7' C8' C9' -177.82(11) . . . . ?
C7' C8' C9' C10' 0.39(19) . . . . ?
C8' C9' C10' C11' 0.15(19) . . . . ?
C8' C9' C10' C15' -179.05(12) . . . . ?
C9' C10' C11' C12' -0.29(19) . . . . ?
C15' C10' C11' C12' 178.93(12) . . . . ?
C10' C11' C12' C7' -0.12(19) . . . . ?
C8' C7' C12' C11' 0.66(19) . . . . ?
N1' C7' C12' C11' 177.69(11) . . . . ?
C7' N1' C13' O1' 159.95(13) . . . . ?
C14' N1' C13' O1' -5.1(2) . . . . ?
C7' N1' C13' C1' -24.77(18) . . . . ?
C14' N1' C13' C1' 170.16(12) . . . . ?
C2' C1' C13' O1' -59.48(18) . . . . ?
C6' C1' C13' O1' 113.13(16) . . . . ?
C2' C1' C13' N1' 125.10(13) . . . . ?
C6' C1' C13' N1' -62.30(17) . . . . ?
C9' C10' C15' F3A' -3.7(6) . . . . ?
C11' C10' C15' F3A' 177.1(5) . . . . ?
C9' C10' C15' F2B' 129.3(4) . . . . ?
C11' C10' C15' F2B' -49.9(5) . . . . ?
C9' C10' C15' F1B' -107.9(11) . . . . ?
C11' C10' C15' F1B' 72.9(11) . . . . ?
C9' C10' C15' F2A' 116.2(6) . . . . ?
C11' C10' C15' F2A' -63.1(6) . . . . ?
C9' C10' C15' F3B' 8.6(8) . . . . ?
C11' C10' C15' F3B' -170.6(8) . . . . ?
C9' C10' C15' F1A' -128.4(4) . . . . ?
C11' C10' C15' F1A' 52.4(4) . . . . ?
C5' C4' C16' F4B' 149.0(12) . . . . ?
C3' C4' C16' F4B' -32.8(12) . . . . ?
C5' C4' C16' F5A' 9.2(6) . . . . ?
C3' C4' C16' F5A' -172.7(5) . . . . ?
C5' C4' C16' F5B' 19.8(8) . . . . ?
C3' C4' C16' F5B' -162.0(7) . . . . ?
C5' C4' C16' F6A' -122.2(4) . . . . ?
C3' C4' C16' F6A' 56.0(4) . . . . ?
C5' C4' C16' F4A' 127.2(2) . . . . ?
C3' C4' C16' F4A' -54.6(3) . . . . ?
C5' C4' C16' F6B' -85.8(10) . . . . ?
C3' C4' C16' F6B' 92.4(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        30.67
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.053
