# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_266
_database_code_depnum_ccdc_archive 'CCDC 1437995'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_audit_creation_date             2014-10-30
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '1(C17 H13 F3 N4 O)'
_chemical_formula_sum            'C17 H13 F3 N4 O'
_chemical_formula_weight         346.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N4 H5'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   14.1362(7)
_cell_length_b                   14.3909(5)
_cell_length_c                   18.0057(8)
_cell_angle_alpha                66.933(4)
_cell_angle_beta                 67.968(4)
_cell_angle_gamma                89.570(3)
_cell_volume                     3081.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8277
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      30.2670
_cell_measurement_theta_min      2.4290
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33672
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.93
_diffrn_reflns_theta_min         2.03
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8656
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   17.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -30.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -19.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   52.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -19.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -90.00  -46.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  178.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -10.00   15.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362 -117.0000   78.2004 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   14.00   65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  -99.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  -34.00   36.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  -57.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   49.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  178.0000   30.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0218562000
_diffrn_orient_matrix_UB_12      -0.0487284000
_diffrn_orient_matrix_UB_13      0.0358850000
_diffrn_orient_matrix_UB_21      -0.0399888000
_diffrn_orient_matrix_UB_22      -0.0036496000
_diffrn_orient_matrix_UB_23      -0.0139725000
_diffrn_orient_matrix_UB_31      0.0305554000
_diffrn_orient_matrix_UB_32      -0.0236856000
_diffrn_orient_matrix_UB_33      -0.0266278000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                11789
_reflns_number_total             16899
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1001
_refine_ls_number_reflns         16899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.026
_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)+(0.0490P)²+0.0490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1225
_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     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
F3C F 0.90209(7) 0.49552(8) -0.10400(6) 0.0302(2) Uani 1 1 d . . .
F2A F 0.21954(9) 0.42244(7) 0.84568(7) 0.0387(3) Uani 1 1 d . . .
F3A F 0.29316(9) 0.41134(8) 0.72155(7) 0.0440(3) Uani 1 1 d . . .
N1 N 1.04675(10) 0.67717(10) 0.55944(9) 0.0218(3) Uani 1 1 d . . .
F2C F 0.88256(7) 0.61629(8) -0.06059(8) 0.0425(3) Uani 1 1 d . . .
F2 F 0.94539(8) 0.87387(8) 0.56291(7) 0.0364(3) Uani 1 1 d . . .
F3B F 0.08457(8) 0.74742(9) 0.69151(8) 0.0436(3) Uani 1 1 d . . .
F1B F 0.11899(8) 0.66633(9) 0.80490(7) 0.0409(3) Uani 1 1 d . . .
F1C F 0.88981(7) 0.46538(9) 0.02562(7) 0.0363(3) Uani 1 1 d . . .
F1A F 0.37302(8) 0.38516(8) 0.80717(7) 0.0378(3) Uani 1 1 d . . .
F3 F 1.10241(7) 0.87341(7) 0.48196(7) 0.0375(3) Uani 1 1 d . . .
N15 N 0.81471(10) 0.73539(10) 0.51703(9) 0.0217(3) Uani 1 1 d . . .
O14B O 0.56597(10) 0.86896(11) 0.68625(8) 0.0349(3) Uani 1 1 d . . .
F1 F 0.98635(7) 0.89485(7) 0.42926(6) 0.0303(2) Uani 1 1 d . . .
F2B F 0.13685(8) 0.60255(8) 0.71199(7) 0.0384(3) Uani 1 1 d . . .
O14 O 1.07328(10) 0.41050(10) 0.69276(10) 0.0398(3) Uani 1 1 d . . .
O14A O 0.14039(12) -0.02718(12) 0.80033(9) 0.0461(4) Uani 1 1 d . . .
O14C O 0.41770(10) 0.59773(9) 0.13952(9) 0.0373(3) Uani 1 1 d . . .
C4 C 0.87479(11) 0.57503(12) 0.57142(10) 0.0174(3) Uani 1 1 d . . .
N2B N 0.40252(10) 0.81686(11) 0.67009(9) 0.0254(3) Uani 1 1 d . . .
C6 C 0.97852(11) 0.72847(12) 0.53353(10) 0.0192(3) Uani 1 1 d . . .
N15A N 0.24522(11) 0.23606(11) 0.98981(9) 0.0233(3) Uani 1 1 d . . .
N1C N 0.68546(10) 0.55430(10) 0.02972(9) 0.0201(3) Uani 1 1 d . . .
N1A N 0.21710(10) 0.21930(11) 0.80150(9) 0.0245(3) Uani 1 1 d . . .
N2 N 1.03215(10) 0.57527(10) 0.59280(9) 0.0211(3) Uani 1 1 d . . .
N2C N 0.58259(10) 0.53411(10) 0.07188(9) 0.0197(3) Uani 1 1 d . . .
C8 C 0.93827(11) 0.41089(12) 0.63912(10) 0.0183(3) Uani 1 1 d . . .
C3B C 0.45723(12) 0.83887(12) 0.58397(10) 0.0199(3) Uani 1 1 d . . .
N22 N 0.76300(14) 0.74545(14) 0.38040(11) 0.0378(4) Uani 1 1 d . . .
N1B N 0.30457(10) 0.76844(11) 0.71055(9) 0.0255(3) Uani 1 1 d . . .
N15B N 0.26594(10) 0.73586(11) 0.53147(9) 0.0238(3) Uani 1 1 d . . .
C10C C 0.24915(13) 0.31809(14) 0.21518(12) 0.0297(4) Uani 1 1 d . . .
H10C H 0.2102 0.2553 0.2335 0.036 Uiso 1 1 calc R . .
N2A N 0.17772(10) 0.12106(11) 0.83400(9) 0.0242(3) Uani 1 1 d . . .
C5 C 0.88656(11) 0.68110(12) 0.53945(10) 0.0177(3) Uani 1 1 d . . .
C3A C 0.15747(11) 0.05849(12) 0.91887(10) 0.0184(3) Uani 1 1 d . . .
C10A C 0.03571(12) -0.22000(13) 1.06574(12) 0.0258(4) Uani 1 1 d . . .
H10A H 0.0108 -0.2642 1.1253 0.031 Uiso 1 1 calc R . .
C13 C 0.99977(12) 0.36091(12) 0.68424(11) 0.0225(3) Uani 1 1 d . . .
C13A C 0.10814(13) -0.08630(14) 0.88744(12) 0.0274(4) Uani 1 1 d . . .
C3 C 0.94791(11) 0.52415(12) 0.59872(10) 0.0173(3) Uani 1 1 d . . .
C8B C 0.56508(12) 0.89165(12) 0.54481(11) 0.0203(3) Uani 1 1 d . . .
C8C C 0.41678(11) 0.42828(12) 0.14049(10) 0.0187(3) Uani 1 1 d . . .
C6A C 0.23583(12) 0.25710(12) 0.85160(10) 0.0212(3) Uani 1 1 d . . .
C3C C 0.53015(11) 0.44435(11) 0.09053(10) 0.0174(3) Uani 1 1 d . . .
C4A C 0.17980(11) 0.09405(12) 0.97306(10) 0.0173(3) Uani 1 1 d . . .
C9 C 0.86502(13) 0.34998(13) 0.63562(11) 0.0256(4) Uani 1 1 d . . .
H9 H 0.8245 0.3815 0.6055 0.031 Uiso 1 1 calc R . .
C16 C 0.71417(12) 0.68911(12) 0.53577(11) 0.0203(3) Uani 1 1 d . . .
C16A C 0.23883(12) 0.17301(11) 1.07613(10) 0.0196(3) Uani 1 1 d . . .
C4B C 0.41430(12) 0.81208(12) 0.53574(11) 0.0209(3) Uani 1 1 d . . .
C8A C 0.11363(11) -0.04935(12) 0.94851(10) 0.0195(3) Uani 1 1 d . . .
C6B C 0.26061(12) 0.74412(12) 0.66599(11) 0.0222(3) Uani 1 1 d . . .
C5B C 0.31207(12) 0.76450(11) 0.57524(11) 0.0199(3) Uani 1 1 d . . .
C13C C 0.36647(12) 0.50558(12) 0.16185(10) 0.0221(3) Uani 1 1 d . . .
C16B C 0.32268(11) 0.74487(12) 0.44349(10) 0.0198(3) Uani 1 1 d . . .
N15C N 0.74177(11) 0.32665(11) -0.01169(10) 0.0239(3) Uani 1 1 d . . .
C11C C 0.20161(12) 0.39579(14) 0.23321(11) 0.0271(4) Uani 1 1 d . . .
H11C H 0.1301 0.3855 0.2629 0.033 Uiso 1 1 calc R . .
C5C C 0.68780(12) 0.39333(12) 0.01723(10) 0.0199(3) Uani 1 1 d . . .
C11A C 0.03262(12) -0.25462(13) 1.00455(12) 0.0281(4) Uani 1 1 d . . .
H11A H 0.0055 -0.3224 1.0232 0.034 Uiso 1 1 calc R . .
C17A C 0.14428(14) 0.13560(13) 1.14746(11) 0.0292(4) Uani 1 1 d . . .
H17A H 0.0844 0.1531 1.1391 0.035 Uiso 1 1 calc R . .
C6C C 0.73668(11) 0.48800(11) 0.00346(10) 0.0184(3) Uani 1 1 d . . .
C19B C 0.43309(16) 0.75782(19) 0.27581(14) 0.0475(6) Uani 1 1 d . . .
H19B H 0.4705 0.7622 0.2193 0.057 Uiso 1 1 calc R . .
N22C N 0.65596(15) 0.16648(18) 0.15695(15) 0.0318(4) Uani 0.85 1 d P A 1
C16C C 0.69930(18) 0.23100(18) 0.00001(14) 0.0205(5) Uani 0.85 1 d P A 1
C21 C 0.69133(13) 0.69504(12) 0.46504(11) 0.0246(4) Uani 1 1 d . . .
C17B C 0.35961(12) 0.83929(13) 0.37188(12) 0.0280(4) Uani 1 1 d . . .
H17B H 0.3471 0.8986 0.3805 0.034 Uiso 1 1 calc R . .
C12 C 0.98528(13) 0.25391(13) 0.72378(11) 0.0255(4) Uani 1 1 d . . .
H12 H 1.0265 0.2211 0.7527 0.031 Uiso 1 1 calc R . .
C7C C 0.85274(12) 0.51743(12) -0.03426(11) 0.0233(3) Uani 1 1 d . A .
C5A C 0.22007(11) 0.19686(12) 0.94069(10) 0.0180(3) Uani 1 1 d . . .
C19 C 0.51979(14) 0.60406(13) 0.57138(14) 0.0340(4) Uani 1 1 d . . .
H19 H 0.4545 0.5742 0.5835 0.041 Uiso 1 1 calc R . .
N22B N 0.29883(14) 0.56012(13) 0.50080(14) 0.0426(4) Uani 1 1 d . . .
C21C C 0.66087(15) 0.15146(18) 0.08431(19) 0.0239(5) Uani 0.85 1 d P A 1
C11 C 0.91084(13) 0.19657(13) 0.72044(11) 0.0275(4) Uani 1 1 d . . .
H11 H 0.9007 0.1255 0.7484 0.033 Uiso 1 1 calc R . .
C21B C 0.34056(12) 0.65463(13) 0.43153(12) 0.0267(4) Uani 1 1 d . . .
C19C C 0.6264(2) 0.03952(19) 0.0227(3) 0.0349(7) Uani 0.85 1 d P A 1
H19C H 0.6013 -0.0248 0.0307 0.042 Uiso 0.85 1 calc PR A 1
C4C C 0.58071(12) 0.37277(12) 0.06300(11) 0.0197(3) Uani 1 1 d . . .
C17 C 0.64037(12) 0.64352(12) 0.62230(12) 0.0273(4) Uani 1 1 d . . .
H17 H 0.6566 0.6421 0.6682 0.033 Uiso 1 1 calc R . .
C17C C 0.70275(17) 0.21329(19) -0.07170(17) 0.0267(5) Uani 0.85 1 d P A 1
H17C H 0.7301 0.2666 -0.1279 0.032 Uiso 0.85 1 calc PR A 1
C7A C 0.27970(14) 0.36892(14) 0.80587(11) 0.0292(4) Uani 1 1 d . . .
C10B C 0.72428(13) 0.98045(13) 0.41477(12) 0.0273(4) Uani 1 1 d . . .
H10B H 0.7605 1.0074 0.3538 0.033 Uiso 1 1 calc R . .
C13B C 0.61375(12) 0.90189(13) 0.59769(11) 0.0237(3) Uani 1 1 d . . .
C10 C 0.85089(14) 0.24477(13) 0.67534(12) 0.0318(4) Uani 1 1 d . . .
H10 H 0.8014 0.2062 0.6720 0.038 Uiso 1 1 calc R . .
C9A C 0.07653(12) -0.11863(12) 1.03667(11) 0.0222(3) Uani 1 1 d . . .
H9A H 0.0792 -0.0961 1.0778 0.027 Uiso 1 1 calc R . .
C12B C 0.71750(13) 0.94831(13) 0.55766(12) 0.0285(4) Uani 1 1 d . . .
H12B H 0.7504 0.9523 0.5926 0.034 Uiso 1 1 calc R . .
C7B C 0.15081(13) 0.69005(14) 0.71945(11) 0.0282(4) Uani 1 1 d . . .
C9C C 0.35535(12) 0.33516(13) 0.16954(11) 0.0265(4) Uani 1 1 d . . .
H9C H 0.3871 0.2827 0.1577 0.032 Uiso 1 1 calc R . .
C12C C 0.25890(12) 0.48772(13) 0.20768(11) 0.0262(4) Uani 1 1 d . . .
H12C H 0.2259 0.5388 0.2210 0.031 Uiso 1 1 calc R . .
N22A N 0.42489(13) 0.19111(15) 1.01779(17) 0.0694(7) Uani 1 1 d . . .
H22G H 0.4702 0.1523 1.0272 0.083 Uiso 1 1 d R . .
H22H H 0.4220 0.1973 0.9688 0.083 Uiso 1 1 d R . .
C11B C 0.77137(13) 0.98799(13) 0.46786(12) 0.0277(4) Uani 1 1 d . . .
H11B H 0.8397 1.0201 0.4424 0.033 Uiso 1 1 calc R . .
C9B C 0.62288(12) 0.93228(12) 0.45386(11) 0.0247(4) Uani 1 1 d . . .
H9B H 0.5919 0.9267 0.4181 0.030 Uiso 1 1 calc R . .
C20 C 0.59102(14) 0.65097(14) 0.48504(13) 0.0332(4) Uani 1 1 d . . .
H20 H 0.5729 0.6536 0.4397 0.040 Uiso 1 1 calc R . .
C7 C 1.00406(12) 0.84242(12) 0.50195(11) 0.0239(3) Uani 1 1 d . . .
C20B C 0.39709(15) 0.66383(17) 0.34551(14) 0.0394(5) Uani 1 1 d . . .
H20B H 0.4102 0.6052 0.3358 0.047 Uiso 1 1 calc R . .
C18 C 0.54302(14) 0.60033(14) 0.64012(13) 0.0344(4) Uani 1 1 d . . .
H18 H 0.4937 0.5691 0.6979 0.041 Uiso 1 1 calc R . .
C12A C 0.06927(13) -0.18949(14) 0.91738(13) 0.0306(4) Uani 1 1 d . . .
H12A H 0.0685 -0.2141 0.8769 0.037 Uiso 1 1 calc R . .
C20A C 0.3197(2) 0.08578(16) 1.1742(2) 0.0611(8) Uani 1 1 d . . .
H20A H 0.3787 0.0694 1.1847 0.073 Uiso 1 1 calc R . .
C18C C 0.66643(16) 0.11830(18) -0.06068(17) 0.0349(5) Uani 0.85 1 d P A 1
H18C H 0.6688 0.1074 -0.1089 0.042 Uiso 0.85 1 calc PR A 1
C20C C 0.62325(17) 0.05505(19) 0.09466(18) 0.0339(5) Uani 0.85 1 d P A 1
H20C H 0.5959 0.0011 0.1505 0.041 Uiso 0.85 1 calc PR A 1
C18B C 0.41498(14) 0.84642(17) 0.28762(13) 0.0416(5) Uani 1 1 d . . .
H18B H 0.4397 0.9100 0.2396 0.050 Uiso 1 1 calc R . .
C21A C 0.32973(15) 0.14959(13) 1.08733(14) 0.0355(5) Uani 1 1 d . . .
C19A C 0.2239(3) 0.04805(17) 1.24296(17) 0.0627(8) Uani 1 1 d . . .
H19A H 0.2188 0.0046 1.2990 0.075 Uiso 1 1 calc R . .
C18A C 0.1369(2) 0.07305(15) 1.23043(13) 0.0489(6) Uani 1 1 d . . .
H18A H 0.0726 0.0480 1.2777 0.059 Uiso 1 1 calc R . .
H15A H 0.2602(15) 0.2980(15) 0.9717(13) 0.035(6) Uiso 1 1 d . . .
H4B H 0.4564(12) 0.8240(13) 0.4753(11) 0.020(4) Uiso 1 1 d . . .
H4A H 0.1679(12) 0.0501(13) 1.0304(11) 0.018(4) Uiso 1 1 d . . .
H4C H 0.5437(12) 0.3110(13) 0.0750(11) 0.022(4) Uiso 1 1 d . . .
H4 H 0.8169(13) 0.5372(13) 0.5767(11) 0.021(4) Uiso 1 1 d . . .
H22E H 0.7538(19) 0.7322(19) 0.3385(17) 0.068(8) Uiso 1 1 d . . .
H15 H 0.8272(15) 0.8043(16) 0.4950(13) 0.041(6) Uiso 1 1 d . . .
H22C H 0.3307(16) 0.5085(17) 0.4935(14) 0.049(6) Uiso 1 1 d . . .
H22A H 0.651(2) 0.110(2) 0.202(2) 0.060(9) Uiso 0.85 1 d P B 1
H15C H 0.8058(16) 0.3465(15) -0.0444(13) 0.038(6) Uiso 1 1 d . . .
H22D H 0.2722(16) 0.5556(17) 0.5565(15) 0.049(7) Uiso 1 1 d . . .
H14 H 1.079(2) 0.480(2) 0.6572(18) 0.083(9) Uiso 1 1 d . . .
H14C H 0.490(2) 0.592(2) 0.1147(17) 0.080(8) Uiso 1 1 d . . .
H22F H 0.8319(19) 0.7520(19) 0.3737(16) 0.067(8) Uiso 1 1 d . . .
H14A H 0.155(2) 0.037(2) 0.7897(17) 0.072(8) Uiso 1 1 d . . .
H14B H 0.500(2) 0.843(2) 0.7012(16) 0.070(8) Uiso 1 1 d . . .
H22B H 0.700(2) 0.216(2) 0.1463(16) 0.044(8) Uiso 0.85 1 d P C 1
H15B H 0.1960(16) 0.7164(15) 0.5555(13) 0.040(6) Uiso 1 1 d . . .
C2S C 0.6218(9) 0.0432(11) 0.1575(11) 0.042(3) Uani 0.15 1 d P A 2
H2S H 0.6002 0.0011 0.2173 0.050 Uiso 0.15 1 calc PR A 2
C5S C 0.6845(10) 0.1751(11) -0.0265(9) 0.0267(5) Uani 0.15 1 d P A 2
C3S C 0.6175(11) 0.0077(11) 0.0978(11) 0.0339(5) Uani 0.15 1 d P A 2
H3S H 0.5934 -0.0614 0.1180 0.041 Uiso 0.15 1 calc PR A 2
C1S C 0.6618(11) 0.1486(12) 0.1209(13) 0.0239(5) Uani 0.15 1 d P A 2
H1S H 0.6693 0.1769 0.1572 0.029 Uiso 0.15 1 calc PR A 2
C1A C 0.6894(14) 0.2096(15) 0.0333(12) 0.0205(5) Uani 0.15 1 d P A 2
C4S C 0.6468(17) 0.0693(15) 0.011(2) 0.0349(7) Uani 0.15 1 d P A 2
H4S H 0.6418 0.0405 -0.0261 0.042 Uiso 0.15 1 calc PR A 2
N1S N 0.7170(9) 0.2367(10) -0.1121(7) 0.0318(4) Uani 0.15 1 d P A 2
H1SA H 0.7420 0.3000 -0.1313 0.038 Uiso 0.15 1 calc PR A 2
H1SB H 0.7131 0.2132 -0.1482 0.038 Uiso 0.15 1 calc PR A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3C C7C 1.3462(18) . ?
F2A C7A 1.3400(19) . ?
F3A C7A 1.3314(19) . ?
N1 C6 1.3229(19) . ?
N1 N2 1.3323(18) . ?
F2C C7C 1.3255(18) . ?
F2 C7 1.3409(18) . ?
F3B C7B 1.352(2) . ?
F1B C7B 1.3257(19) . ?
F1C C7C 1.3353(19) . ?
F1A C7A 1.352(2) . ?
F3 C7 1.3302(18) . ?
N15 C5 1.3614(19) . ?
N15 C16 1.434(2) . ?
N15 H15 0.90(2) . ?
O14B C13B 1.352(2) . ?
O14B H14B 0.90(3) . ?
F1 C7 1.3469(19) . ?
F2B C7B 1.3411(19) . ?
O14 C13 1.352(2) . ?
O14 H14 0.94(3) . ?
O14A C13A 1.348(2) . ?
O14A H14A 0.88(3) . ?
O14C C13C 1.350(2) . ?
O14C H14C 0.97(3) . ?
C4 C5 1.390(2) . ?
C4 C3 1.391(2) . ?
C4 H4 0.940(17) . ?
N2B C3B 1.350(2) . ?
N2B N1B 1.3391(19) . ?
C6 C5 1.421(2) . ?
C6 C7 1.506(2) . ?
N15A C16A 1.427(2) . ?
N15A C5A 1.3627(19) . ?
N15A H15A 0.82(2) . ?
N1C N2C 1.3345(17) . ?
N1C C6C 1.3207(18) . ?
N1A N2A 1.3304(19) . ?
N1A C6A 1.321(2) . ?
N2 C3 1.3516(19) . ?
N2C C3C 1.3484(19) . ?
C8 C13 1.413(2) . ?
C8 C3 1.485(2) . ?
C8 C9 1.397(2) . ?
C3B C8B 1.480(2) . ?
C3B C4B 1.390(2) . ?
N22 C21 1.364(2) . ?
N22 H22E 0.90(3) . ?
N22 H22F 0.94(3) . ?
N1B C6B 1.323(2) . ?
N15B C5B 1.364(2) . ?
N15B C16B 1.4342(19) . ?
N15B H15B 0.91(2) . ?
C10C H10C 0.9300 . ?
C10C C11C 1.385(2) . ?
C10C C9C 1.382(2) . ?
N2A C3A 1.351(2) . ?
C3A C4A 1.392(2) . ?
C3A C8A 1.481(2) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.389(2) . ?
C10A C9A 1.387(2) . ?
C13 C12 1.399(2) . ?
C13A C8A 1.422(2) . ?
C13A C12A 1.400(2) . ?
C8B C13B 1.416(2) . ?
C8B C9B 1.394(2) . ?
C8C C3C 1.481(2) . ?
C8C C13C 1.417(2) . ?
C8C C9C 1.397(2) . ?
C6A C5A 1.421(2) . ?
C6A C7A 1.499(2) . ?
C3C C4C 1.393(2) . ?
C4A C5A 1.393(2) . ?
C4A H4A 0.923(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(2) . ?
C16 C21 1.399(2) . ?
C16 C17 1.391(2) . ?
C16A C17A 1.381(2) . ?
C16A C21A 1.393(2) . ?
C4B C5B 1.388(2) . ?
C4B H4B 0.968(16) . ?
C8A C9A 1.390(2) . ?
C6B C5B 1.422(2) . ?
C6B C7B 1.501(2) . ?
C13C C12C 1.399(2) . ?
C16B C17B 1.383(2) . ?
C16B C21B 1.404(2) . ?
N15C C5C 1.3625(18) . ?
N15C C16C 1.411(3) . ?
N15C H15C 0.85(2) . ?
N15C C1A 1.59(2) . ?
C11C H11C 0.9300 . ?
C11C C12C 1.370(2) . ?
C5C C6C 1.420(2) . ?
C5C C4C 1.392(2) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.362(3) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.373(3) . ?
C6C C7C 1.511(2) . ?
C19B H19B 0.9300 . ?
C19B C20B 1.366(3) . ?
C19B C18B 1.380(3) . ?
N22C C21C 1.384(3) . ?
N22C H22A 0.88(3) . ?
N22C H22B 0.86(3) . ?
C16C C21C 1.392(3) . ?
C16C C17C 1.395(3) . ?
C21 C20 1.412(2) . ?
C17B H17B 0.9300 . ?
C17B C18B 1.383(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.375(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(3) . ?
C19 C18 1.377(3) . ?
N22B C21B 1.373(2) . ?
N22B H22C 0.89(2) . ?
N22B H22D 0.91(2) . ?
C21C C20C 1.406(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.387(2) . ?
C21B C20B 1.403(3) . ?
C19C H19C 0.9300 . ?
C19C C18C 1.378(5) . ?
C19C C20C 1.383(5) . ?
C4C H4C 0.940(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(2) . ?
C17C H17C 0.9300 . ?
C17C C18C 1.376(3) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.389(2) . ?
C10B C9B 1.381(2) . ?
C13B C12B 1.400(2) . ?
C10 H10 0.9300 . ?
C9A H9A 0.9300 . ?
C12B H12B 0.9300 . ?
C12B C11B 1.371(2) . ?
C9C H9C 0.9300 . ?
C12C H12C 0.9300 . ?
N22A H22G 0.8678 . ?
N22A H22H 0.8680 . ?
N22A C21A 1.377(3) . ?
C11B H11B 0.9300 . ?
C9B H9B 0.9300 . ?
C20 H20 0.9300 . ?
C20B H20B 0.9300 . ?
C18 H18 0.9300 . ?
C12A H12A 0.9300 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.422(3) . ?
C20A C19A 1.374(4) . ?
C18C H18C 0.9300 . ?
C20C H20C 0.9300 . ?
C18B H18B 0.9300 . ?
C19A H19A 0.9300 . ?
C19A C18A 1.353(4) . ?
C18A H18A 0.9300 . ?
C2S H2S 0.9300 . ?
C2S C3S 1.38(2) . ?
C2S C1S 1.42(2) . ?
C5S C1A 1.37(2) . ?
C5S C4S 1.41(2) . ?
C5S N1S 1.334(16) . ?
C3S H3S 0.9300 . ?
C3S C4S 1.36(3) . ?
C1S H1S 0.9300 . ?
C1S C1A 1.37(2) . ?
C4S H4S 0.9300 . ?
N1S H1SA 0.8600 . ?
N1S H1SB 0.8600 . ?

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 N1 N2 120.46(13) . . ?
C5 N15 C16 123.56(13) . . ?
C5 N15 H15 119.0(13) . . ?
C16 N15 H15 117.1(13) . . ?
C13B O14B H14B 105.7(16) . . ?
C13 O14 H14 106.0(17) . . ?
C13A O14A H14A 109.8(17) . . ?
C13C O14C H14C 104.2(15) . . ?
C5 C4 C3 119.47(14) . . ?
C5 C4 H4 120.8(10) . . ?
C3 C4 H4 119.6(10) . . ?
N1B N2B C3B 119.79(13) . . ?
N1 C6 C5 123.71(14) . . ?
N1 C6 C7 113.56(13) . . ?
C5 C6 C7 122.64(13) . . ?
C16A N15A H15A 117.8(14) . . ?
C5A N15A C16A 122.12(13) . . ?
C5A N15A H15A 119.9(14) . . ?
C6C N1C N2C 120.40(13) . . ?
C6A N1A N2A 120.75(14) . . ?
N1 N2 C3 119.69(13) . . ?
N1C N2C C3C 120.27(12) . . ?
C13 C8 C3 121.84(14) . . ?
C9 C8 C13 117.75(14) . . ?
C9 C8 C3 120.39(14) . . ?
N2B C3B C8B 116.16(13) . . ?
N2B C3B C4B 121.45(14) . . ?
C4B C3B C8B 122.39(14) . . ?
C21 N22 H22E 117.4(17) . . ?
C21 N22 H22F 115.6(15) . . ?
H22E N22 H22F 114(2) . . ?
C6B N1B N2B 120.27(14) . . ?
C5B N15B C16B 121.95(13) . . ?
C5B N15B H15B 120.2(12) . . ?
C16B N15B H15B 117.6(12) . . ?
C11C C10C H10C 120.5 . . ?
C9C C10C H10C 120.5 . . ?
C9C C10C C11C 119.01(16) . . ?
N1A N2A C3A 120.00(13) . . ?
N15 C5 C4 122.68(14) . . ?
N15 C5 C6 122.49(14) . . ?
C4 C5 C6 114.82(13) . . ?
N2A C3A C4A 121.22(14) . . ?
N2A C3A C8A 115.70(13) . . ?
C4A C3A C8A 123.06(15) . . ?
C11A C10A H10A 120.5 . . ?
C9A C10A H10A 120.5 . . ?
C9A C10A C11A 119.05(17) . . ?
O14 C13 C8 123.86(14) . . ?
O14 C13 C12 116.47(15) . . ?
C12 C13 C8 119.66(15) . . ?
O14A C13A C8A 123.33(15) . . ?
O14A C13A C12A 117.12(15) . . ?
C12A C13A C8A 119.54(16) . . ?
C4 C3 C8 123.26(13) . . ?
N2 C3 C4 121.76(14) . . ?
N2 C3 C8 114.95(13) . . ?
C13B C8B C3B 121.68(15) . . ?
C9B C8B C3B 120.73(14) . . ?
C9B C8B C13B 117.58(14) . . ?
C13C C8C C3C 121.68(14) . . ?
C9C C8C C3C 120.92(13) . . ?
C9C C8C C13C 117.39(14) . . ?
N1A C6A C5A 123.39(14) . . ?
N1A C6A C7A 114.59(14) . . ?
C5A C6A C7A 121.98(14) . . ?
N2C C3C C8C 115.76(12) . . ?
N2C C3C C4C 121.31(14) . . ?
C4C C3C C8C 122.92(14) . . ?
C3A C4A C5A 119.73(15) . . ?
C3A C4A H4A 120.6(10) . . ?
C5A C4A H4A 119.7(10) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.09(16) . . ?
C10 C9 H9 119.0 . . ?
C21 C16 N15 118.44(14) . . ?
C17 C16 N15 120.13(14) . . ?
C17 C16 C21 121.38(15) . . ?
C17A C16A N15A 120.75(15) . . ?
C17A C16A C21A 120.38(16) . . ?
C21A C16A N15A 118.87(15) . . ?
C3B C4B H4B 120.1(10) . . ?
C5B C4B C3B 120.03(15) . . ?
C5B C4B H4B 119.9(10) . . ?
C13A C8A C3A 121.09(15) . . ?
C9A C8A C3A 121.72(13) . . ?
C9A C8A C13A 117.19(15) . . ?
N1B C6B C5B 123.83(15) . . ?
N1B C6B C7B 114.65(14) . . ?
C5B C6B C7B 121.51(14) . . ?
N15B C5B C4B 122.67(14) . . ?
N15B C5B C6B 122.68(14) . . ?
C4B C5B C6B 114.60(14) . . ?
O14C C13C C8C 122.94(14) . . ?
O14C C13C C12C 117.34(14) . . ?
C12C C13C C8C 119.71(15) . . ?
C17B C16B N15B 121.59(14) . . ?
C17B C16B C21B 120.32(15) . . ?
C21B C16B N15B 118.09(15) . . ?
C5C N15C C16C 125.97(15) . . ?
C5C N15C H15C 117.6(13) . . ?
C5C N15C C1A 118.6(6) . . ?
C16C N15C H15C 116.1(13) . . ?
C16C N15C C1A 18.5(6) . . ?
C1A N15C H15C 122.3(14) . . ?
C10C C11C H11C 119.7 . . ?
C12C C11C C10C 120.65(15) . . ?
C12C C11C H11C 119.7 . . ?
N15C C5C C6C 122.48(14) . . ?
N15C C5C C4C 122.13(14) . . ?
C4C C5C C6C 115.39(13) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A C10A 120.16(16) . . ?
C12A C11A H11A 119.9 . . ?
C16A C17A H17A 119.4 . . ?
C18A C17A C16A 121.30(19) . . ?
C18A C17A H17A 119.4 . . ?
N1C C6C C5C 123.30(13) . . ?
N1C C6C C7C 113.50(13) . . ?
C5C C6C C7C 122.93(13) . . ?
C20B C19B H19B 119.4 . . ?
C20B C19B C18B 121.22(18) . . ?
C18B C19B H19B 119.4 . . ?
C21C N22C H22A 114.5(18) . . ?
C21C N22C H22B 115.9(16) . . ?
H22A N22C H22B 113(3) . . ?
C21C C16C N15C 118.42(19) . . ?
C21C C16C C17C 120.2(2) . . ?
C17C C16C N15C 121.24(19) . . ?
N22 C21 C16 120.27(16) . . ?
N22 C21 C20 122.30(16) . . ?
C16 C21 C20 117.37(15) . . ?
C16B C17B H17B 119.6 . . ?
C18B C17B C16B 120.72(16) . . ?
C18B C17B H17B 119.6 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.85(16) . . ?
C11 C12 H12 119.6 . . ?
F3C C7C C6C 112.77(13) . . ?
F2C C7C F3C 106.83(13) . . ?
F2C C7C F1C 107.61(13) . . ?
F2C C7C C6C 112.88(12) . . ?
F1C C7C F3C 105.71(12) . . ?
F1C C7C C6C 110.64(14) . . ?
N15A C5A C6A 122.53(14) . . ?
N15A C5A C4A 122.61(15) . . ?
C4A C5A C6A 114.84(14) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.53(17) . . ?
C21B N22B H22C 115.4(14) . . ?
C21B N22B H22D 118.9(14) . . ?
H22C N22B H22D 116(2) . . ?
N22C C21C C16C 121.6(2) . . ?
N22C C21C C20C 120.3(3) . . ?
C16C C21C C20C 118.1(2) . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.00(16) . . ?
C10 C11 H11 120.0 . . ?
N22B C21B C16B 121.19(16) . . ?
N22B C21B C20B 120.78(17) . . ?
C20B C21B C16B 117.91(17) . . ?
C18C C19C H19C 119.6 . . ?
C18C C19C C20C 120.7(2) . . ?
C20C C19C H19C 119.6 . . ?
C3C C4C H4C 121.0(9) . . ?
C5C C4C C3C 119.27(15) . . ?
C5C C4C H4C 119.7(9) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.08(16) . . ?
C18 C17 H17 120.0 . . ?
C16C C17C H17C 119.4 . . ?
C18C C17C C16C 121.1(2) . . ?
C18C C17C H17C 119.4 . . ?
F2A C7A F1A 105.99(13) . . ?
F2A C7A C6A 111.87(14) . . ?
F3A C7A F2A 107.42(14) . . ?
F3A C7A F1A 106.75(14) . . ?
F3A C7A C6A 113.31(14) . . ?
F1A C7A C6A 111.09(14) . . ?
C11B C10B H10B 120.5 . . ?
C9B C10B H10B 120.5 . . ?
C9B C10B C11B 118.98(16) . . ?
O14B C13B C8B 123.85(15) . . ?
O14B C13B C12B 116.81(15) . . ?
C12B C13B C8B 119.35(16) . . ?
C9 C10 C11 119.63(16) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10A C9A C8A 122.64(14) . . ?
C10A C9A H9A 118.7 . . ?
C8A C9A H9A 118.7 . . ?
C13B C12B H12B 119.4 . . ?
C11B C12B C13B 121.18(15) . . ?
C11B C12B H12B 119.4 . . ?
F3B C7B C6B 111.46(15) . . ?
F1B C7B F3B 107.05(13) . . ?
F1B C7B F2B 106.86(14) . . ?
F1B C7B C6B 113.57(14) . . ?
F2B C7B F3B 105.69(14) . . ?
F2B C7B C6B 111.75(13) . . ?
C10C C9C C8C 122.42(15) . . ?
C10C C9C H9C 118.8 . . ?
C8C C9C H9C 118.8 . . ?
C13C C12C H12C 119.6 . . ?
C11C C12C C13C 120.77(15) . . ?
C11C C12C H12C 119.6 . . ?
H22G N22A H22H 108.5 . . ?
C21A N22A H22G 110.2 . . ?
C21A N22A H22H 110.9 . . ?
C10B C11B H11B 119.9 . . ?
C12B C11B C10B 120.24(16) . . ?
C12B C11B H11B 119.9 . . ?
C8B C9B H9B 118.7 . . ?
C10B C9B C8B 122.62(15) . . ?
C10B C9B H9B 118.7 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.34(16) . . ?
C19 C20 H20 119.8 . . ?
F2 C7 F1 105.95(12) . . ?
F2 C7 C6 111.49(13) . . ?
F3 C7 F2 107.35(13) . . ?
F3 C7 F1 106.79(13) . . ?
F3 C7 C6 112.93(13) . . ?
F1 C7 C6 111.92(13) . . ?
C19B C20B C21B 120.79(17) . . ?
C19B C20B H20B 119.6 . . ?
C21B C20B H20B 119.6 . . ?
C19 C18 C17 119.27(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C13A C12A H12A 119.3 . . ?
C11A C12A C13A 121.37(15) . . ?
C11A C12A H12A 119.3 . . ?
C21A C20A H20A 119.6 . . ?
C19A C20A H20A 119.6 . . ?
C19A C20A C21A 120.7(2) . . ?
C19C C18C H18C 120.4 . . ?
C17C C18C C19C 119.2(2) . . ?
C17C C18C H18C 120.4 . . ?
C21C C20C H20C 119.6 . . ?
C19C C20C C21C 120.8(3) . . ?
C19C C20C H20C 119.6 . . ?
C19B C18B C17B 119.03(19) . . ?
C19B C18B H18B 120.5 . . ?
C17B C18B H18B 120.5 . . ?
C16A C21A C20A 117.0(2) . . ?
N22A C21A C16A 121.00(19) . . ?
N22A C21A C20A 121.9(2) . . ?
C20A C19A H19A 119.5 . . ?
C18A C19A C20A 121.0(2) . . ?
C18A C19A H19A 119.5 . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A C17A 119.5(2) . . ?
C19A C18A H18A 120.2 . . ?
C3S C2S H2S 122.5 . . ?
C3S C2S C1S 114.9(16) . . ?
C1S C2S H2S 122.5 . . ?
C1A C5S C4S 113.9(18) . . ?
N1S C5S C1A 121.8(15) . . ?
N1S C5S C4S 124.2(18) . . ?
C2S C3S H3S 118.6 . . ?
C4S C3S C2S 122.9(15) . . ?
C4S C3S H3S 118.6 . . ?
H22A C1S H22B 65(2) . . ?
H22A C1S H1S 46.4 . . ?
H22B C1S H1S 20.6 . . ?
C2S C1S H22A 73.3(16) . . ?
C2S C1S H22B 138(2) . . ?
C2S C1S H1S 119.3 . . ?
C1A C1S H22A 165(2) . . ?
C1A C1S H22B 100.3(16) . . ?
C1A C1S C2S 121.3(19) . . ?
C1A C1S H1S 119.3 . . ?
C5S C1A N15C 112.8(13) . . ?
C1S C1A N15C 122.8(14) . . ?
C1S C1A C5S 124.1(18) . . ?
C5S C4S H4S 118.6 . . ?
C3S C4S C5S 123(2) . . ?
C3S C4S H4S 118.6 . . ?
C5S N1S H1SA 120.0 . . ?
C5S N1S H1SB 120.0 . . ?
H1SA N1S H1SB 120.0 . . ?

####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 1437996'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 F3 N5 O'
_chemical_formula_weight         388.38

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'
O O 0.0106 0.0060 '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'
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_H-M   C2/c

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                   11.0546(15)
_cell_length_b                   19.664(3)
_cell_length_c                   17.9966(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.746(10)
_cell_angle_gamma                90.00
_cell_volume                     3765.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1557
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur S CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8604
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.1174
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4349
_reflns_number_gt                1557
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0170P)²+0.0000P] 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         4349
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.37098(11) 0.12863(7) 0.20386(8) 0.1028(5) Uani 1 1 d . . .
N1 N 0.03336(14) -0.00691(8) 0.15574(9) 0.0506(4) Uani 1 1 d . . .
O1 O 0.33685(12) 0.28564(7) 0.19096(7) 0.0647(4) Uani 1 1 d . . .
C1 C 0.35099(18) 0.32578(10) 0.24400(11) 0.0456(5) Uani 1 1 d . . .
N2 N 0.14125(15) 0.01849(8) 0.19868(9) 0.0568(5) Uani 1 1 d . . .
F2 F 0.28049(15) 0.15201(9) 0.28823(8) 0.1345(6) Uani 1 1 d . . .
C2 C 0.25598(18) 0.33648(11) 0.28762(12) 0.0791(7) Uani 1 1 d . . .
H2A H 0.1846 0.3078 0.2667 0.119 Uiso 1 1 calc R . .
H2B H 0.2298 0.3832 0.2833 0.119 Uiso 1 1 calc R . .
H2C H 0.2922 0.3254 0.3410 0.119 Uiso 1 1 calc R . .
N3 N 0.13365(15) 0.19096(8) 0.12468(9) 0.0493(4) Uani 1 1 d . . .
C3 C 0.17349(17) 0.08103(10) 0.18933(10) 0.0496(5) Uani 1 1 d . . .
F3 F 0.35645(13) 0.05401(8) 0.28453(9) 0.1534(8) Uani 1 1 d . . .
C4 C 0.10027(17) 0.12669(10) 0.13455(10) 0.0441(5) Uani 1 1 d . . .
N4 N 0.1185(3) 0.19206(12) -0.03289(16) 0.0942(8) Uani 1 1 d . . .
C5 C -0.01199(18) 0.09911(10) 0.09164(11) 0.0438(5) Uani 1 1 d . . .
N5 N 0.45393(14) 0.36348(8) 0.26926(9) 0.0440(4) Uani 1 1 d . . .
C6 C -0.04238(16) 0.03357(9) 0.10286(10) 0.0413(5) Uani 1 1 d . . .
C7 C 0.2954(2) 0.10233(15) 0.24202(16) 0.0837(8) Uani 1 1 d . . .
C8 C -0.16054(16) 0.00341(9) 0.05761(12) 0.0440(5) Uani 1 1 d . . .
C9 C -0.22611(18) -0.04082(10) 0.09104(12) 0.0605(6) Uani 1 1 d . . .
H9A H -0.1946 -0.0524 0.1428 0.073 Uiso 1 1 calc R . .
C10 C -0.3379(2) -0.06808(11) 0.04864(15) 0.0770(7) Uani 1 1 d . . .
H10A H -0.3818 -0.0981 0.0717 0.092 Uiso 1 1 calc R . .
C11 C -0.3845(2) -0.05117(11) -0.02739(16) 0.0767(7) Uani 1 1 d . . .
H11A H -0.4605 -0.0695 -0.0559 0.092 Uiso 1 1 calc R . .
C12 C -0.3206(2) -0.00784(11) -0.06146(12) 0.0684(6) Uani 1 1 d . . .
H12A H -0.3525 0.0035 -0.1133 0.082 Uiso 1 1 calc R . .
C13 C -0.20834(17) 0.01939(9) -0.01925(12) 0.0542(5) Uani 1 1 d . . .
H13A H -0.1644 0.0489 -0.0429 0.065 Uiso 1 1 calc R . .
C14 C 0.05020(17) 0.23552(9) 0.07255(11) 0.0419(5) Uani 1 1 d . . .
C15 C 0.04689(19) 0.23548(10) -0.00494(12) 0.0495(5) Uani 1 1 d . . .
C16 C -0.0372(2) 0.27896(11) -0.05378(11) 0.0607(6) Uani 1 1 d . . .
H16A H -0.0403 0.2802 -0.1059 0.073 Uiso 1 1 calc R . .
C17 C -0.1140(2) 0.31933(11) -0.02708(14) 0.0675(7) Uani 1 1 d . . .
H17A H -0.1700 0.3479 -0.0610 0.081 Uiso 1 1 calc R . .
C18 C -0.1110(2) 0.31891(11) 0.04902(16) 0.0744(7) Uani 1 1 d . . .
H18A H -0.1643 0.3469 0.0673 0.089 Uiso 1 1 calc R . .
C19 C -0.0282(2) 0.27663(11) 0.09836(11) 0.0592(6) Uani 1 1 d . . .
H19A H -0.0257 0.2761 0.1504 0.071 Uiso 1 1 calc R . .
H5A H -0.0697(13) 0.1283(7) 0.0568(8) 0.035(5) Uiso 1 1 d . . .
H5 H 0.4583(15) 0.4024(9) 0.3010(9) 0.067(6) Uiso 1 1 d . . .
H4A H 0.1775(17) 0.1720(10) -0.0022(11) 0.066(8) Uiso 1 1 d . . .
H4B H 0.130(2) 0.1995(11) -0.0797(13) 0.101(10) Uiso 1 1 d . . .
H3 H 0.2086(15) 0.2107(8) 0.1543(9) 0.059(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
F1 C7 1.322(3) . ?
N1 N2 1.3300(18) . ?
N1 C6 1.3445(19) . ?
O1 C1 1.2156(19) . ?
C1 N5 1.331(2) . ?
C1 C2 1.487(2) . ?
N2 C3 1.304(2) . ?
F2 C7 1.322(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N3 C4 1.342(2) . ?
N3 C14 1.424(2) . ?
N3 H3 0.939(16) . ?
C3 C4 1.414(2) . ?
C3 C7 1.483(3) . ?
F3 C7 1.290(2) . ?
C4 C5 1.382(2) . ?
N4 C15 1.351(3) . ?
N4 H4A 0.830(17) . ?
N4 H4B 0.90(2) . ?
C5 C6 1.361(2) . ?
C5 H5A 0.954(14) . ?
N5 N5 1.379(3) 2_655 ?
N5 H5 0.948(17) . ?
C6 C8 1.464(2) . ?
C8 C9 1.371(2) . ?
C8 C13 1.376(2) . ?
C9 C10 1.373(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.355(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(2) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C19 1.356(2) . ?
C14 C15 1.385(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.343(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.361(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C6 118.48(16) . . ?
O1 C1 N5 123.08(18) . . ?
O1 C1 C2 123.21(19) . . ?
N5 C1 C2 113.70(18) . . ?
C3 N2 N1 120.84(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 N3 C14 120.95(16) . . ?
C4 N3 H3 123.1(10) . . ?
C14 N3 H3 115.7(10) . . ?
N2 C3 C4 124.33(17) . . ?
N2 C3 C7 114.65(19) . . ?
C4 C3 C7 121.0(2) . . ?
N3 C4 C5 122.22(18) . . ?
N3 C4 C3 124.35(17) . . ?
C5 C4 C3 113.42(19) . . ?
C15 N4 H4A 119.1(15) . . ?
C15 N4 H4B 119.6(15) . . ?
H4A N4 H4B 114(2) . . ?
C6 C5 C4 120.60(19) . . ?
C6 C5 H5A 121.2(9) . . ?
C4 C5 H5A 118.0(9) . . ?
C1 N5 N5 120.55(17) . 2_655 ?
C1 N5 H5 123.7(11) . . ?
N5 N5 H5 112.3(10) 2_655 . ?
N1 C6 C5 122.30(18) . . ?
N1 C6 C8 116.37(17) . . ?
C5 C6 C8 121.33(18) . . ?
F3 C7 F1 107.1(2) . . ?
F3 C7 F2 107.8(2) . . ?
F1 C7 F2 104.0(2) . . ?
F3 C7 C3 114.2(2) . . ?
F1 C7 C3 111.8(2) . . ?
F2 C7 C3 111.3(2) . . ?
C9 C8 C13 118.76(17) . . ?
C9 C8 C6 120.72(19) . . ?
C13 C8 C6 120.52(18) . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C8 C13 C12 120.60(19) . . ?
C8 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C19 C14 C15 120.03(18) . . ?
C19 C14 N3 120.07(18) . . ?
C15 C14 N3 119.88(19) . . ?
N4 C15 C14 121.1(2) . . ?
N4 C15 C16 120.9(2) . . ?
C14 C15 C16 117.9(2) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 H18A 120.5 . . ?
C19 C18 H18A 120.5 . . ?
C14 C19 C18 121.10(19) . . ?
C14 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.032

