# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_ijsf1201
_audit_creation_date             2012-04-24
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H19 F3 N2 O3'
_chemical_formula_sum            'C21 H19 F3 N2 O3'
_chemical_formula_weight         404.38
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H19 F3 N2 O3'
_chemical_oxdiff_usercomment     'Toms TJW/5/143/450/1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7492(3)
_cell_length_b                   9.0043(3)
_cell_length_c                   24.1842(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.900(3)
_cell_angle_gamma                90.00
_cell_volume                     1882.30(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5381
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      27.8109
_cell_measurement_theta_min      3.1089
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3796
_exptl_crystal_size_mid          0.1807
_exptl_crystal_size_min          0.0328
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14377
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.12
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -61.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365 -178.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -78.00  -51.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365 -178.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -30.00   96.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8303    0.0000 -150.0000 126

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   77.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8303 -141.0000  -29.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00    9.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365   57.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega  -92.00    8.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365  -77.0000  -30.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0097380000
_diffrn_orient_matrix_UB_12      0.0026536000
_diffrn_orient_matrix_UB_13      -0.0296944000
_diffrn_orient_matrix_UB_21      -0.0294622000
_diffrn_orient_matrix_UB_22      0.0732094000
_diffrn_orient_matrix_UB_23      0.0005393000
_diffrn_orient_matrix_UB_31      0.0759031000
_diffrn_orient_matrix_UB_32      0.0287956000
_diffrn_orient_matrix_UB_33      0.0013631000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7201
_reflns_number_total             8188
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.5706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1135
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1628(2) 0.3711(3) 0.53527(10) 0.0220(5) Uani 1 1 d . . .
C2 C 0.0627(2) 0.2876(3) 0.48914(9) 0.0201(5) Uani 1 1 d . . .
H2 H -0.0385 0.2700 0.5006 0.024 Uiso 1 1 calc R . .
C3 C 0.1362(3) 0.1356(3) 0.47892(9) 0.0196(5) Uani 1 1 d . . .
H3A H 0.1630 0.0850 0.5145 0.023 Uiso 1 1 calc R . .
H3B H 0.0602 0.0753 0.4555 0.023 Uiso 1 1 calc R . .
C4 C 0.2785(2) 0.1482(3) 0.45141(9) 0.0184(5) Uani 1 1 d . . .
C5 C 0.2724(2) 0.1561(3) 0.39190(9) 0.0188(5) Uani 1 1 d . . .
C6 C 0.1541(3) 0.1410(3) 0.34624(9) 0.0226(5) Uani 1 1 d . . .
H6 H 0.0526 0.1247 0.3518 0.027 Uiso 1 1 calc R . .
C7 C 0.1908(3) 0.1508(3) 0.29254(10) 0.0259(5) Uani 1 1 d . . .
H7 H 0.1132 0.1394 0.2619 0.031 Uiso 1 1 calc R . .
C8 C 0.3425(3) 0.1774(3) 0.28374(10) 0.0271(6) Uani 1 1 d . . .
H8 H 0.3633 0.1850 0.2473 0.032 Uiso 1 1 calc R . .
C9 C 0.4620(3) 0.1926(3) 0.32778(9) 0.0247(5) Uani 1 1 d . . .
H9 H 0.5630 0.2097 0.3218 0.030 Uiso 1 1 calc R . .
C10 C 0.4251(2) 0.1814(3) 0.38186(9) 0.0191(5) Uani 1 1 d . . .
C11 C 0.4308(2) 0.1676(3) 0.47499(9) 0.0173(4) Uani 1 1 d . . .
C12 C 0.5091(2) 0.1706(3) 0.53346(9) 0.0179(4) Uani 1 1 d . . .
C13 C 0.6321(3) 0.2683(3) 0.54958(9) 0.0229(5) Uani 1 1 d . . .
H13 H 0.6633 0.3318 0.5231 0.028 Uiso 1 1 calc R . .
C14 C 0.7079(3) 0.2723(3) 0.60389(10) 0.0239(5) Uani 1 1 d . . .
H14 H 0.7889 0.3386 0.6139 0.029 Uiso 1 1 calc R . .
C15 C 0.6635(3) 0.1775(3) 0.64369(9) 0.0222(5) Uani 1 1 d . . .
C16 C 0.5426(3) 0.0775(3) 0.62865(9) 0.0241(5) Uani 1 1 d . . .
H16 H 0.5127 0.0138 0.6553 0.029 Uiso 1 1 calc R . .
C17 C 0.4673(3) 0.0733(3) 0.57391(9) 0.0226(5) Uani 1 1 d . . .
H17 H 0.3880 0.0052 0.5638 0.027 Uiso 1 1 calc R . .
C18 C 0.2592(3) 0.3801(4) 0.63124(11) 0.0378(7) Uani 1 1 d . . .
H18A H 0.3648 0.3762 0.6249 0.057 Uiso 1 1 calc R . .
H18B H 0.2498 0.3291 0.6654 0.057 Uiso 1 1 calc R . .
H18C H 0.2284 0.4818 0.6340 0.057 Uiso 1 1 calc R . .
C19 C -0.0834(3) 0.3729(3) 0.40043(10) 0.0226(5) Uani 1 1 d . . .
C20 C -0.0845(3) 0.4746(3) 0.35091(10) 0.0310(6) Uani 1 1 d . . .
H20A H -0.0148 0.5559 0.3611 0.047 Uiso 1 1 calc R . .
H20B H -0.1872 0.5122 0.3395 0.047 Uiso 1 1 calc R . .
H20C H -0.0521 0.4205 0.3205 0.047 Uiso 1 1 calc R . .
C21 C 0.7388(3) 0.1876(3) 0.70357(10) 0.0283(6) Uani 1 1 d . . .
F1 F 0.88076(17) 0.2472(2) 0.70945(6) 0.0412(4) Uani 1 1 d . . .
F2 F 0.65734(19) 0.2721(2) 0.73441(6) 0.0450(5) Uani 1 1 d . . .
F3 F 0.7543(2) 0.0553(2) 0.72878(7) 0.0469(5) Uani 1 1 d . . .
N1 N 0.0412(2) 0.3807(2) 0.44009(8) 0.0200(4) Uani 1 1 d . . .
H1 H 0.1119 0.4445 0.4361 0.024 Uiso 1 1 calc R . .
N2 N 0.5184(2) 0.1904(2) 0.43276(7) 0.0186(4) Uani 1 1 d . . .
H2A H 0.620(3) 0.198(3) 0.4372(10) 0.019(6) Uiso 1 1 d . . .
O1 O 0.1605(2) 0.3092(2) 0.58499(7) 0.0308(4) Uani 1 1 d . . .
O2 O 0.23705(19) 0.4804(2) 0.52751(7) 0.0303(4) Uani 1 1 d . . .
O3 O -0.19022(18) 0.2872(3) 0.40432(7) 0.0339(5) Uani 1 1 d . . .
C22 C 0.1505(2) 0.7248(3) 0.02831(9) 0.0197(5) Uani 1 1 d . . .
C23 C 0.0497(2) 0.6447(3) -0.01873(9) 0.0203(5) Uani 1 1 d . . .
H23 H -0.0530 0.6311 -0.0081 0.024 Uiso 1 1 calc R . .
C24 C 0.1167(2) 0.4893(3) -0.02893(9) 0.0205(5) Uani 1 1 d . . .
H24A H 0.1369 0.4367 0.0064 0.025 Uiso 1 1 calc R . .
H24B H 0.0396 0.4334 -0.0536 0.025 Uiso 1 1 calc R . .
C25 C 0.2637(2) 0.4947(3) -0.05416(9) 0.0173(4) Uani 1 1 d . . .
C26 C 0.2669(2) 0.4937(3) -0.11332(9) 0.0183(4) Uani 1 1 d . . .
C27 C 0.1535(3) 0.4778(3) -0.16087(9) 0.0214(5) Uani 1 1 d . . .
H27 H 0.0493 0.4720 -0.1573 0.026 Uiso 1 1 calc R . .
C28 C 0.1994(3) 0.4709(3) -0.21307(10) 0.0243(5) Uani 1 1 d . . .
H28 H 0.1252 0.4587 -0.2447 0.029 Uiso 1 1 calc R . .
C29 C 0.3566(3) 0.4819(3) -0.21907(10) 0.0244(5) Uani 1 1 d . . .
H29 H 0.3844 0.4771 -0.2546 0.029 Uiso 1 1 calc R . .
C30 C 0.4699(3) 0.4997(3) -0.17332(9) 0.0214(5) Uani 1 1 d . . .
H30 H 0.5735 0.5079 -0.1774 0.026 Uiso 1 1 calc R . .
C31 C 0.4238(2) 0.5052(3) -0.12056(9) 0.0180(5) Uani 1 1 d . . .
C32 C 0.4141(2) 0.5068(3) -0.02808(9) 0.0178(5) Uani 1 1 d . . .
C33 C 0.4830(2) 0.5069(3) 0.03150(9) 0.0178(5) Uani 1 1 d . . .
C34 C 0.6000(3) 0.6056(3) 0.05213(10) 0.0236(5) Uani 1 1 d . . .
H34 H 0.6335 0.6750 0.0281 0.028 Uiso 1 1 calc R . .
C35 C 0.6678(3) 0.6025(3) 0.10798(10) 0.0263(5) Uani 1 1 d . . .
H35 H 0.7457 0.6696 0.1213 0.032 Uiso 1 1 calc R . .
C36 C 0.6187(3) 0.4987(3) 0.14376(9) 0.0242(5) Uani 1 1 d . . .
C37 C 0.5028(3) 0.3987(3) 0.12434(10) 0.0235(5) Uani 1 1 d . . .
H37 H 0.4704 0.3293 0.1486 0.028 Uiso 1 1 calc R . .
C38 C 0.4347(3) 0.4024(3) 0.06833(9) 0.0214(5) Uani 1 1 d . . .
H38 H 0.3567 0.3352 0.0552 0.026 Uiso 1 1 calc R . .
C39 C 0.2413(3) 0.7287(3) 0.12502(10) 0.0336(6) Uani 1 1 d . . .
H39A H 0.2277 0.6775 0.1587 0.050 Uiso 1 1 calc R . .
H39B H 0.2123 0.8310 0.1278 0.050 Uiso 1 1 calc R . .
H39C H 0.3477 0.7228 0.1199 0.050 Uiso 1 1 calc R . .
C40 C -0.0848(3) 0.7312(3) -0.10948(10) 0.0228(5) Uani 1 1 d . . .
C41 C -0.0779(3) 0.8393(3) -0.15650(10) 0.0316(6) Uani 1 1 d . . .
H41A H -0.0343 0.9314 -0.1415 0.047 Uiso 1 1 calc R . .
H41B H -0.1805 0.8565 -0.1761 0.047 Uiso 1 1 calc R . .
H41C H -0.0146 0.7989 -0.1819 0.047 Uiso 1 1 calc R . .
C42 C 0.6867(3) 0.4952(3) 0.20451(10) 0.0316(6) Uani 1 1 d . . .
F4 F 0.8198(2) 0.5696(2) 0.21585(7) 0.0550(5) Uani 1 1 d . . .
F5 F 0.5953(2) 0.5546(4) 0.23679(7) 0.0842(9) Uani 1 1 d . . .
F6 F 0.7218(3) 0.3589(2) 0.22285(8) 0.0643(6) Uani 1 1 d . . .
N3 N 0.0344(2) 0.7404(2) -0.06716(8) 0.0213(4) Uani 1 1 d . . .
H3 H 0.1046 0.8063 -0.0691 0.026 Uiso 1 1 calc R . .
N4 N 0.5103(2) 0.5180(2) -0.06845(8) 0.0180(4) Uani 1 1 d . . .
H4 H 0.608(3) 0.514(3) -0.0604(9) 0.010(6) Uiso 1 1 d . . .
O4 O 0.1443(2) 0.6603(2) 0.07756(6) 0.0275(4) Uani 1 1 d . . .
O5 O 0.22726(18) 0.8335(2) 0.02171(7) 0.0258(4) Uani 1 1 d . . .
O6 O -0.19056(19) 0.6421(2) -0.10921(7) 0.0305(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
C1 C2 1.508(3) . ?
C1 O1 1.329(3) . ?
C1 O2 1.210(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.548(3) . ?
C2 N1 1.441(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.505(3) . ?
C4 C5 1.434(3) . ?
C4 C11 1.377(3) . ?
C5 C6 1.398(3) . ?
C5 C10 1.413(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C10 N2 1.370(3) . ?
C11 C12 1.473(3) . ?
C11 N2 1.384(2) . ?
C12 C13 1.397(3) . ?
C12 C17 1.403(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 C16 1.393(3) . ?
C15 C21 1.498(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 O1 1.451(3) . ?
C19 C20 1.507(3) . ?
C19 N1 1.338(3) . ?
C19 O3 1.226(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 F1 1.340(3) . ?
C21 F2 1.345(3) . ?
C21 F3 1.335(3) . ?
N1 H1 0.8600 . ?
N2 H2A 0.88(2) . ?
C22 C23 1.511(3) . ?
C22 O4 1.334(3) . ?
C22 O5 1.211(3) . ?
C23 H23 0.9800 . ?
C23 C24 1.551(3) . ?
C23 N3 1.444(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.507(3) . ?
C25 C26 1.436(3) . ?
C25 C32 1.373(3) . ?
C26 C27 1.405(3) . ?
C26 C31 1.414(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.409(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.376(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.397(3) . ?
C31 N4 1.371(3) . ?
C32 C33 1.473(3) . ?
C32 N4 1.388(3) . ?
C33 C34 1.389(3) . ?
C33 C38 1.404(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.389(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.386(3) . ?
C36 C37 1.383(3) . ?
C36 C42 1.498(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.393(3) . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C39 O4 1.454(3) . ?
C40 C41 1.505(4) . ?
C40 N3 1.346(3) . ?
C40 O6 1.225(3) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 F4 1.334(3) . ?
C42 F5 1.315(3) . ?
C42 F6 1.325(4) . ?
N3 H3 0.8600 . ?
N4 H4 0.85(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
O1 C1 C2 111.8(2) . . ?
O2 C1 C2 123.7(2) . . ?
O2 C1 O1 124.4(2) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 110.54(19) . . ?
C3 C2 H2 108.5 . . ?
N1 C2 C1 107.8(2) . . ?
N1 C2 H2 108.5 . . ?
N1 C2 C3 112.80(17) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.39(19) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C4 C3 122.9(2) . . ?
C11 C4 C3 129.8(2) . . ?
C11 C4 C5 107.03(18) . . ?
C6 C5 C4 134.1(2) . . ?
C6 C5 C10 118.95(19) . . ?
C10 C5 C4 106.93(19) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117.2(2) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 C5 122.3(2) . . ?
N2 C10 C5 107.61(18) . . ?
N2 C10 C9 130.1(2) . . ?
C4 C11 C12 132.57(19) . . ?
C4 C11 N2 108.91(18) . . ?
N2 C11 C12 118.50(19) . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 C17 118.1(2) . . ?
C17 C12 C11 121.7(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 C21 120.3(2) . . ?
C16 C15 C21 119.6(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
N1 C19 C20 116.2(2) . . ?
O3 C19 C20 122.2(2) . . ?
O3 C19 N1 121.6(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F1 C21 C15 112.9(2) . . ?
F1 C21 F2 106.1(2) . . ?
F2 C21 C15 112.2(2) . . ?
F3 C21 C15 112.7(2) . . ?
F3 C21 F1 106.4(2) . . ?
F3 C21 F2 106.0(2) . . ?
C2 N1 H1 118.4 . . ?
C19 N1 C2 123.2(2) . . ?
C19 N1 H1 118.4 . . ?
C10 N2 C11 109.49(18) . . ?
C10 N2 H2A 124.2(15) . . ?
C11 N2 H2A 125.8(15) . . ?
C1 O1 C18 115.0(2) . . ?
O4 C22 C23 111.4(2) . . ?
O5 C22 C23 123.9(2) . . ?
O5 C22 O4 124.7(2) . . ?
C22 C23 H23 108.3 . . ?
C22 C23 C24 111.07(19) . . ?
C24 C23 H23 108.3 . . ?
N3 C23 C22 107.2(2) . . ?
N3 C23 H23 108.3 . . ?
N3 C23 C24 113.53(17) . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.74(19) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C26 C25 C24 123.59(19) . . ?
C32 C25 C24 129.34(19) . . ?
C32 C25 C26 107.03(17) . . ?
C27 C26 C25 134.09(19) . . ?
C27 C26 C31 118.84(19) . . ?
C31 C26 C25 106.99(19) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 C26 118.9(2) . . ?
C28 C27 H27 120.6 . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C29 121.1(2) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.2(2) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 H30 121.1 . . ?
C29 C30 C31 117.7(2) . . ?
C31 C30 H30 121.1 . . ?
C30 C31 C26 122.2(2) . . ?
N4 C31 C26 107.50(18) . . ?
N4 C31 C30 130.3(2) . . ?
C25 C32 C33 131.84(19) . . ?
C25 C32 N4 108.97(19) . . ?
N4 C32 C33 119.17(19) . . ?
C34 C33 C32 121.2(2) . . ?
C34 C33 C38 118.6(2) . . ?
C38 C33 C32 120.2(2) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.1(2) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.6(2) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 C42 120.8(2) . . ?
C37 C36 C35 120.6(2) . . ?
C37 C36 C42 118.6(2) . . ?
C36 C37 H37 120.2 . . ?
C36 C37 C38 119.7(2) . . ?
C38 C37 H37 120.2 . . ?
C33 C38 H38 119.8 . . ?
C37 C38 C33 120.5(2) . . ?
C37 C38 H38 119.8 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O4 C39 H39A 109.5 . . ?
O4 C39 H39B 109.5 . . ?
O4 C39 H39C 109.5 . . ?
N3 C40 C41 114.7(2) . . ?
O6 C40 C41 123.1(2) . . ?
O6 C40 N3 122.2(2) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
F4 C42 C36 113.1(2) . . ?
F5 C42 C36 112.8(2) . . ?
F5 C42 F4 105.4(3) . . ?
F5 C42 F6 108.0(3) . . ?
F6 C42 C36 112.6(2) . . ?
F6 C42 F4 104.3(2) . . ?
C23 N3 H3 118.5 . . ?
C40 N3 C23 122.9(2) . . ?
C40 N3 H3 118.5 . . ?
C31 N4 C32 109.40(18) . . ?
C31 N4 H4 126.9(15) . . ?
C32 N4 H4 122.4(15) . . ?
C22 O4 C39 114.9(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
C1 C2 C3 C4 -71.3(2) . . . . ?
C1 C2 N1 C19 -152.2(2) . . . . ?
C2 C1 O1 C18 177.6(2) . . . . ?
C2 C3 C4 C5 -86.2(3) . . . . ?
C2 C3 C4 C11 87.3(3) . . . . ?
C3 C2 N1 C19 85.5(2) . . . . ?
C3 C4 C5 C6 -7.3(4) . . . . ?
C3 C4 C5 C10 174.5(2) . . . . ?
C3 C4 C11 C12 5.8(5) . . . . ?
C3 C4 C11 N2 -173.0(2) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C4 C5 C10 C9 178.9(2) . . . . ?
C4 C5 C10 N2 -0.8(3) . . . . ?
C4 C11 C12 C13 -143.1(3) . . . . ?
C4 C11 C12 C17 39.2(4) . . . . ?
C4 C11 N2 C10 -1.9(3) . . . . ?
C5 C4 C11 C12 -179.9(2) . . . . ?
C5 C4 C11 N2 1.3(3) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C5 C10 N2 C11 1.6(3) . . . . ?
C6 C5 C10 C9 0.3(4) . . . . ?
C6 C5 C10 N2 -179.4(2) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C8 C9 C10 N2 179.4(3) . . . . ?
C9 C10 N2 C11 -178.0(3) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
C11 C4 C5 C6 178.0(3) . . . . ?
C11 C4 C5 C10 -0.3(3) . . . . ?
C11 C12 C13 C14 -179.5(2) . . . . ?
C11 C12 C17 C16 179.8(2) . . . . ?
C12 C11 N2 C10 179.2(2) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C13 C14 C15 C21 -176.3(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C21 F1 -24.4(3) . . . . ?
C14 C15 C21 F2 95.4(3) . . . . ?
C14 C15 C21 F3 -145.0(2) . . . . ?
C15 C16 C17 C12 -1.2(4) . . . . ?
C16 C15 C21 F1 159.0(2) . . . . ?
C16 C15 C21 F2 -81.2(3) . . . . ?
C16 C15 C21 F3 38.4(3) . . . . ?
C17 C12 C13 C14 -1.7(4) . . . . ?
C20 C19 N1 C2 -177.8(2) . . . . ?
C21 C15 C16 C17 176.6(2) . . . . ?
N1 C2 C3 C4 49.4(3) . . . . ?
N2 C11 C12 C13 35.6(3) . . . . ?
N2 C11 C12 C17 -142.1(2) . . . . ?
O1 C1 C2 C3 -70.4(2) . . . . ?
O1 C1 C2 N1 165.95(18) . . . . ?
O2 C1 C2 C3 109.0(3) . . . . ?
O2 C1 C2 N1 -14.7(3) . . . . ?
O2 C1 O1 C18 -1.7(3) . . . . ?
O3 C19 N1 C2 2.0(4) . . . . ?
C22 C23 C24 C25 -70.1(2) . . . . ?
C22 C23 N3 C40 -156.4(2) . . . . ?
C23 C22 O4 C39 178.6(2) . . . . ?
C23 C24 C25 C26 -90.6(3) . . . . ?
C23 C24 C25 C32 86.7(3) . . . . ?
C24 C23 N3 C40 80.6(2) . . . . ?
C24 C25 C26 C27 -5.3(4) . . . . ?
C24 C25 C26 C31 177.9(2) . . . . ?
C24 C25 C32 C33 5.4(4) . . . . ?
C24 C25 C32 N4 -175.8(2) . . . . ?
C25 C26 C27 C28 -175.1(3) . . . . ?
C25 C26 C31 C30 176.6(2) . . . . ?
C25 C26 C31 N4 -2.0(3) . . . . ?
C25 C32 C33 C34 -137.6(3) . . . . ?
C25 C32 C33 C38 44.7(4) . . . . ?
C25 C32 N4 C31 -3.2(3) . . . . ?
C26 C25 C32 C33 -177.0(2) . . . . ?
C26 C25 C32 N4 1.9(3) . . . . ?
C26 C27 C28 C29 -1.0(4) . . . . ?
C26 C31 N4 C32 3.2(3) . . . . ?
C27 C26 C31 C30 -0.7(4) . . . . ?
C27 C26 C31 N4 -179.4(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 0.6(4) . . . . ?
C29 C30 C31 C26 -0.3(4) . . . . ?
C29 C30 C31 N4 178.1(3) . . . . ?
C30 C31 N4 C32 -175.3(3) . . . . ?
C31 C26 C27 C28 1.3(4) . . . . ?
C32 C25 C26 C27 176.8(3) . . . . ?
C32 C25 C26 C31 0.1(3) . . . . ?
C32 C33 C34 C35 -178.1(2) . . . . ?
C32 C33 C38 C37 177.9(2) . . . . ?
C33 C32 N4 C31 175.8(2) . . . . ?
C33 C34 C35 C36 0.4(4) . . . . ?
C34 C33 C38 C37 0.2(3) . . . . ?
C34 C35 C36 C37 -0.2(4) . . . . ?
C34 C35 C36 C42 -178.4(2) . . . . ?
C35 C36 C37 C38 0.0(4) . . . . ?
C35 C36 C42 F4 -16.9(4) . . . . ?
C35 C36 C42 F5 102.7(3) . . . . ?
C35 C36 C42 F6 -134.8(3) . . . . ?
C36 C37 C38 C33 0.0(3) . . . . ?
C37 C36 C42 F4 164.8(2) . . . . ?
C37 C36 C42 F5 -75.6(3) . . . . ?
C37 C36 C42 F6 47.0(3) . . . . ?
C38 C33 C34 C35 -0.4(3) . . . . ?
C41 C40 N3 C23 -179.0(2) . . . . ?
C42 C36 C37 C38 178.2(2) . . . . ?
N3 C23 C24 C25 50.8(3) . . . . ?
N4 C32 C33 C34 43.6(3) . . . . ?
N4 C32 C33 C38 -134.0(2) . . . . ?
O4 C22 C23 C24 -68.8(2) . . . . ?
O4 C22 C23 N3 166.62(17) . . . . ?
O5 C22 C23 C24 110.9(2) . . . . ?
O5 C22 C23 N3 -13.7(3) . . . . ?
O5 C22 O4 C39 -1.1(3) . . . . ?
O6 C40 N3 C23 1.4(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0164 -0.0000 -0.0000 -0.9999 0.0297 -0.0005 -0.0014
0 0 1 0.0164 0.0000 0.0000 0.9999 -0.0297 0.0005 0.0014
1 0 0 0.0867 1.0001 0.0001 -0.0001 -0.0097 -0.0295 0.0759
-1 0 0 0.0867 -1.0001 -0.0001 0.0001 0.0097 0.0295 -0.0759
0 -1 0 0.1938 0.0000 -1.0000 -0.0001 -0.0027 -0.0732 -0.0288
0 1 0 0.1858 -0.0000 1.0000 0.0001 0.0027 0.0732 0.0288
2 -1 0 0.1409 2.0001 -0.9999 -0.0003 -0.0221 -0.1321 0.1230

_database_code_depnum_ccdc_archive 'CCDC 968490'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ijsf1202
_audit_creation_date             2012-04-13
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 F N2 O3'
_chemical_formula_sum            'C20 H19 F N2 O3'
_chemical_formula_weight         354.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H19 F1 N2 O3'
_chemical_oxdiff_usercomment     'Tom Williams TJW/5/173/465/1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   21.0404(11)
_cell_length_b                   21.0404(11)
_cell_length_c                   10.4652(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4012.2(6)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      32.0836
_cell_measurement_theta_min      2.9596
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1674
_exptl_crystal_size_max          0.2168
_exptl_crystal_size_mid          0.1531
_exptl_crystal_size_min          0.1393
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9531
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         32.16
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -69.00   48.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -      -25.1672   19.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00  -35.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   77.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -128.0000   -7.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00  100.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -178.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00   62.00   1.0000   12.8400
omega____ theta____ kappa____ phi______ frames
    -       26.4172   56.0000  117.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0179086000
_diffrn_orient_matrix_UB_12      -0.0357576000
_diffrn_orient_matrix_UB_13      0.0267633000
_diffrn_orient_matrix_UB_21      -0.0296459000
_diffrn_orient_matrix_UB_22      -0.0103234000
_diffrn_orient_matrix_UB_23      -0.0430230000
_diffrn_orient_matrix_UB_31      0.0175359000
_diffrn_orient_matrix_UB_32      -0.0111921000
_diffrn_orient_matrix_UB_33      -0.0453332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5157
_reflns_number_total             5613
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
Palatinus, L. & Chapuis, G. (2007).
SUPERFLIP - a computer program for the solution of crystal structures
 by charge flipping in arbitrary dimensions.
J. Appl. Cryst. 40, 786-790.
;
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0412P)²+1.5669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0995
_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. 

The hydrogens on the nitrogens were found by difference map.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54326(9) 0.29788(9) 0.51985(15) 0.0237(3) Uani 1 1 d . . .
C2 C 0.52022(9) 0.34868(9) 0.52482(15) 0.0233(3) Uani 1 1 d . . .
H2 H 0.5149 0.3667 0.6028 0.028 Uiso 1 1 calc R . .
C3 C 0.50511(8) 0.37238(9) 0.41058(14) 0.0196(3) Uani 1 1 d . . .
H3 H 0.4891 0.4063 0.4120 0.024 Uiso 1 1 calc R . .
C4 C 0.51388(8) 0.34549(8) 0.29391(13) 0.0157(3) Uani 1 1 d . . .
C5 C 0.53818(8) 0.29447(8) 0.29351(14) 0.0191(3) Uani 1 1 d . . .
H5 H 0.5446 0.2767 0.2161 0.023 Uiso 1 1 calc R . .
C6 C 0.55282(9) 0.27007(9) 0.40693(16) 0.0229(3) Uani 1 1 d . . .
H6 H 0.5686 0.2359 0.4067 0.027 Uiso 1 1 calc R . .
C7 C 0.49634(8) 0.36751(8) 0.17097(13) 0.0151(2) Uani 1 1 d . . .
C8 C 0.51401(8) 0.43501(8) 0.12255(13) 0.0146(2) Uani 1 1 d . . .
C9 C 0.55844(8) 0.50912(7) 0.18290(14) 0.0161(3) Uani 1 1 d . . .
H9A H 0.5455 0.5056 0.2726 0.019 Uiso 1 1 calc R . .
H9B H 0.5458 0.5429 0.1428 0.019 Uiso 1 1 calc R . .
C10 C 0.64169(7) 0.54050(8) 0.17169(13) 0.0139(2) Uani 1 1 d . . .
H10 H 0.6561 0.5114 0.2248 0.017 Uiso 1 1 calc R . .
C11 C 0.66116(8) 0.53645(8) 0.03302(13) 0.0153(3) Uani 1 1 d . . .
C12 C 0.68382(11) 0.46603(11) -0.11590(16) 0.0309(4) Uani 1 1 d . . .
H12A H 0.6398 0.4503 -0.1647 0.046 Uiso 1 1 calc R . .
H12B H 0.6970 0.4285 -0.1176 0.046 Uiso 1 1 calc R . .
H12C H 0.7228 0.5103 -0.1522 0.046 Uiso 1 1 calc R . .
C13 C 0.75258(8) 0.65834(8) 0.20747(13) 0.0162(3) Uani 1 1 d . . .
C14 C 0.78405(9) 0.73524(9) 0.25806(17) 0.0258(3) Uani 1 1 d . . .
H14A H 0.8185 0.7433 0.3250 0.039 Uiso 1 1 calc R . .
H14B H 0.7452 0.7418 0.2912 0.039 Uiso 1 1 calc R . .
H14C H 0.8086 0.7697 0.1902 0.039 Uiso 1 1 calc R . .
C15 C 0.48395(8) 0.42278(8) -0.00434(13) 0.0154(3) Uani 1 1 d . . .
C16 C 0.48216(8) 0.46893(8) -0.09995(15) 0.0187(3) Uani 1 1 d . . .
H16 H 0.5061 0.5195 -0.0880 0.022 Uiso 1 1 calc R . .
C17 C 0.44428(9) 0.43801(9) -0.21186(15) 0.0219(3) Uani 1 1 d . . .
H17 H 0.4429 0.4682 -0.2754 0.026 Uiso 1 1 calc R . .
C18 C 0.40778(9) 0.36167(9) -0.23109(15) 0.0220(3) Uani 1 1 d . . .
H18 H 0.3818 0.3421 -0.3064 0.026 Uiso 1 1 calc R . .
C19 C 0.40995(8) 0.31516(9) -0.13967(15) 0.0211(3) Uani 1 1 d . . .
H19 H 0.3867 0.2648 -0.1531 0.025 Uiso 1 1 calc R . .
C20 C 0.44815(8) 0.34650(8) -0.02694(14) 0.0165(3) Uani 1 1 d . . .
F1 F 0.55774(7) 0.27429(7) 0.63125(9) 0.0371(3) Uani 1 1 d . . .
N1 N 0.67922(7) 0.61582(7) 0.21652(12) 0.0174(2) Uani 1 1 d . . .
H1 H 0.6540(13) 0.6359(13) 0.241(2) 0.039(6) Uiso 1 1 d . . .
N2 N 0.45744(7) 0.31386(7) 0.08007(12) 0.0179(2) Uani 1 1 d . . .
H2A H 0.4351(13) 0.2686(14) 0.093(2) 0.036(6) Uiso 1 1 d . . .
O1 O 0.66376(6) 0.57685(6) -0.05103(10) 0.0198(2) Uani 1 1 d . . .
O2 O 0.67144(6) 0.47957(6) 0.01536(10) 0.0205(2) Uani 1 1 d . . .
O3 O 0.79097(6) 0.63528(6) 0.16024(10) 0.0196(2) 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
C1 C2 1.378(3) . ?
C1 C6 1.377(2) . ?
C1 F1 1.3600(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(2) . ?
C4 C5 1.401(2) . ?
C4 C7 1.4755(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(2) . ?
C7 N2 1.3876(18) . ?
C8 C9 1.4989(19) . ?
C8 C15 1.4377(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5366(19) . ?
C10 H10 0.9800 . ?
C10 C11 1.5218(19) . ?
C10 N1 1.4503(18) . ?
C11 O1 1.2052(18) . ?
C11 O2 1.3312(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 O2 1.4526(19) . ?
C13 C14 1.505(2) . ?
C13 N1 1.3458(19) . ?
C13 O3 1.2345(17) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.408(2) . ?
C15 C20 1.411(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.406(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(2) . ?
C20 N2 1.3778(19) . ?
N1 H1 0.87(2) . ?
N2 H2A 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.01(14) . . ?
F1 C1 C2 118.73(15) . . ?
F1 C1 C6 118.26(15) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.53(14) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.38(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.07(13) . . ?
C3 C4 C7 122.07(13) . . ?
C5 C4 C7 118.84(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.97(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.04(15) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C8 C7 C4 131.75(13) . . ?
C8 C7 N2 109.46(12) . . ?
N2 C7 C4 118.73(13) . . ?
C7 C8 C9 128.77(13) . . ?
C7 C8 C15 106.77(12) . . ?
C15 C8 C9 124.41(13) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.51(11) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10 109.3 . . ?
C11 C10 C9 109.25(11) . . ?
C11 C10 H10 109.3 . . ?
N1 C10 C9 109.00(11) . . ?
N1 C10 H10 109.3 . . ?
N1 C10 C11 110.79(11) . . ?
O1 C11 C10 125.11(13) . . ?
O1 C11 O2 124.20(13) . . ?
O2 C11 C10 110.62(12) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
N1 C13 C14 115.58(13) . . ?
O3 C13 C14 122.74(13) . . ?
O3 C13 N1 121.68(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C8 133.95(14) . . ?
C16 C15 C20 118.84(13) . . ?
C20 C15 C8 107.18(12) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.03(14) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.06(15) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.06(14) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 121.1 . . ?
C18 C19 C20 117.72(14) . . ?
C20 C19 H19 121.1 . . ?
C19 C20 C15 122.26(13) . . ?
N2 C20 C15 107.62(12) . . ?
N2 C20 C19 130.10(13) . . ?
C10 N1 H1 119.8(16) . . ?
C13 N1 C10 121.37(12) . . ?
C13 N1 H1 118.4(16) . . ?
C7 N2 H2A 125.4(15) . . ?
C20 N2 C7 108.94(12) . . ?
C20 N2 H2A 124.3(15) . . ?
C11 O2 C12 115.68(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.87(2) 2.06(2) 2.9155(16) 170(2) 6_565

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
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C7 178.13(14) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C7 C8 47.4(2) . . . . ?
C3 C4 C7 N2 -135.53(15) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C7 C8 C9 0.3(3) . . . . ?
C4 C7 C8 C15 177.89(14) . . . . ?
C4 C7 N2 C20 -179.18(13) . . . . ?
C5 C4 C7 C8 -134.34(16) . . . . ?
C5 C4 C7 N2 42.70(19) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C7 C4 C5 C6 -177.66(14) . . . . ?
C7 C8 C9 C10 80.64(18) . . . . ?
C7 C8 C15 C16 178.36(15) . . . . ?
C7 C8 C15 C20 0.43(16) . . . . ?
C8 C7 N2 C20 -1.52(16) . . . . ?
C8 C9 C10 C11 50.88(16) . . . . ?
C8 C9 C10 N1 172.07(11) . . . . ?
C8 C15 C16 C17 -176.53(15) . . . . ?
C8 C15 C20 C19 177.08(14) . . . . ?
C8 C15 C20 N2 -1.35(16) . . . . ?
C9 C8 C15 C16 -4.0(2) . . . . ?
C9 C8 C15 C20 178.12(13) . . . . ?
C9 C10 C11 O1 75.70(17) . . . . ?
C9 C10 C11 O2 -101.15(13) . . . . ?
C9 C10 N1 C13 -174.53(13) . . . . ?
C10 C11 O2 C12 174.64(13) . . . . ?
C11 C10 N1 C13 -54.29(17) . . . . ?
C14 C13 N1 C10 -179.88(13) . . . . ?
C15 C8 C9 C10 -96.52(16) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C15 C20 N2 C7 1.77(16) . . . . ?
C16 C15 C20 C19 -1.2(2) . . . . ?
C16 C15 C20 N2 -179.65(13) . . . . ?
C16 C17 C18 C19 -1.4(2) . . . . ?
C17 C18 C19 C20 1.4(2) . . . . ?
C18 C19 C20 C15 -0.1(2) . . . . ?
C18 C19 C20 N2 177.96(15) . . . . ?
C19 C20 N2 C7 -176.50(15) . . . . ?
C20 C15 C16 C17 1.2(2) . . . . ?
F1 C1 C2 C3 -179.67(14) . . . . ?
F1 C1 C6 C5 -179.82(14) . . . . ?
N1 C10 C11 O1 -44.40(19) . . . . ?
N1 C10 C11 O2 138.75(12) . . . . ?
N2 C7 C8 C9 -176.90(13) . . . . ?
N2 C7 C8 C15 0.65(16) . . . . ?
O1 C11 O2 C12 -2.2(2) . . . . ?
O3 C13 N1 C10 0.3(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 1 0 0.0998 -2.0000 0.9990 -0.0002 0.0001 0.0490 -0.0462
2 -1 0 0.1128 2.0000 -0.9990 0.0002 -0.0001 -0.0490 0.0462
0 0 1 0.0890 -0.0001 -0.0002 0.9992 0.0267 -0.0430 -0.0453
0 0 -1 0.0736 0.0001 0.0002 -0.9992 -0.0267 0.0430 0.0453
1 -1 -1 0.0662 0.9999 -0.9990 -0.9991 -0.0089 0.0237 0.0740
-1 1 1 0.0732 -0.9999 0.9990 0.9991 0.0089 -0.0237 -0.0740
-1 0 -1 0.0746 -1.0001 -0.0000 -0.9993 -0.0088 0.0726 0.0278
1 0 1 0.0746 1.0001 0.0000 0.9993 0.0088 -0.0726 -0.0278
1 -2 0 0.0574 0.9996 -1.9986 -0.0001 0.0536 -0.0090 0.0399
-1 2 0 0.0854 -0.9996 1.9986 0.0001 -0.0536 0.0090 -0.0399
-1 -1 0 0.0706 -1.0004 -0.9996 -0.0002 0.0537 0.0400 -0.0063
1 1 0 0.0826 1.0004 0.9996 0.0002 -0.0537 -0.0400 0.0063

_database_code_depnum_ccdc_archive 'CCDC 968491'
