# 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_782
_database_code_depnum_ccdc_archive 'CCDC 1465050'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_audit_creation_date             2015-12-04
_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         'C24 H15 F3 N3 O8, C6 H16 N'
_chemical_formula_sum            'C30 H31 F3 N4 O8'
_chemical_formula_weight         632.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   11.5613(7)
_cell_length_b                   12.0502(7)
_cell_length_c                   13.5247(7)
_cell_angle_alpha                116.093(6)
_cell_angle_beta                 98.200(5)
_cell_angle_gamma                108.429(5)
_cell_volume                     1515.13(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3836
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5990
_cell_measurement_theta_min      2.3500
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89296
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14609
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_min         2.08
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9999
_diffrn_measured_fraction_theta_max 0.8777
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   14.00   43.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -      -20.7924   77.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   17.00   43.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -      -20.7924   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   47.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -      -20.7924   77.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00  -18.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -      -20.7924   77.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   64.00   90.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -       23.2924   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   71.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -       23.2924   77.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega   -7.00   85.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -       23.2924   77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega   -7.00   92.00   1.0000   11.6800
omega____ theta____ kappa____ phi______ frames
    -       23.2924   77.0000   90.0000 99
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0253844000
_diffrn_orient_matrix_UB_12      -0.0280109000
_diffrn_orient_matrix_UB_13      -0.0609451000
_diffrn_orient_matrix_UB_21      -0.0316655000
_diffrn_orient_matrix_UB_22      0.0437248000
_diffrn_orient_matrix_UB_23      0.0101925000
_diffrn_orient_matrix_UB_31      0.0552084000
_diffrn_orient_matrix_UB_32      0.0505253000
_diffrn_orient_matrix_UB_33      0.0032106000
_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                5266
_reflns_number_total             8251
_reflns_odcompleteness_completeness 99.99
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         8251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.003
_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)+(0.1100P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1903
_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
O6 O 0.31366(14) 0.57646(13) 0.01016(13) 0.0519(4) Uani 1 1 d . . .
C16 C 0.32077(14) 0.32867(15) -0.13778(14) 0.0313(3) Uani 1 1 d . . .
C13 C 0.18028(14) 0.09120(15) -0.13473(14) 0.0315(3) Uani 1 1 d . . .
O4 O -0.07606(13) -0.01989(12) -0.26934(12) 0.0509(4) Uani 1 1 d . . .
C12 C 0.17723(15) 0.21686(16) -0.05888(14) 0.0324(3) Uani 1 1 d . . .
C14 C 0.25352(15) 0.08887(16) -0.20845(14) 0.0337(3) Uani 1 1 d . . .
C17 C 0.39359(15) 0.45252(16) -0.13768(14) 0.0347(4) Uani 1 1 d . . .
C6 C 0.00834(15) -0.15759(15) -0.23268(14) 0.0309(3) Uani 1 1 d . . .
C11 C 0.24832(15) 0.33532(15) -0.06207(14) 0.0325(3) Uani 1 1 d . . .
C1 C -0.07847(15) -0.13696(16) -0.30205(14) 0.0340(3) Uani 1 1 d . . .
O7 O 0.18509(15) 0.48406(14) 0.08177(14) 0.0596(4) Uani 1 1 d . . .
C18 C 0.47166(16) 0.45998(18) -0.20653(15) 0.0396(4) Uani 1 1 d . . .
H18 H 0.4785 0.3812 -0.2568 0.048 Uiso 1 1 calc R . .
C9 C 0.10761(15) -0.03169(16) -0.12674(14) 0.0335(3) Uani 1 1 d . . .
C15 C 0.32204(16) 0.20481(16) -0.21085(15) 0.0358(4) Uani 1 1 d . . .
H15 H 0.3691 0.1994 -0.2618 0.043 Uiso 1 1 calc R . .
F1 F 0.36286(13) -0.01452(13) -0.32866(14) 0.0758(4) Uani 1 1 d . . .
N1 N 0.10519(17) 0.22257(17) 0.01168(15) 0.0484(4) Uani 1 1 d . . .
C5 C -0.00031(15) -0.28799(16) -0.26448(14) 0.0331(3) Uani 1 1 d . . .
F3 F 0.15953(13) -0.12625(12) -0.38357(11) 0.0745(4) Uani 1 1 d . . .
C3 C -0.18183(16) -0.38712(17) -0.44358(15) 0.0386(4) Uani 1 1 d . . .
N2 N -0.25879(18) -0.23486(17) -0.47753(15) 0.0534(4) Uani 1 1 d . . .
C2 C -0.16985(16) -0.25722(17) -0.40727(15) 0.0369(4) Uani 1 1 d . . .
C4 C -0.09428(16) -0.39792(16) -0.36959(15) 0.0367(4) Uani 1 1 d . . .
F2 F 0.28022(14) -0.10856(14) -0.23776(15) 0.0753(4) Uani 1 1 d . . .
N3 N -0.10300(17) -0.53484(15) -0.40531(15) 0.0485(4) Uani 1 1 d . . .
O5 O 0.13125(15) -0.02217(14) -0.03192(11) 0.0568(4) Uani 1 1 d . . .
C10 C 0.24476(18) 0.46464(17) 0.01440(16) 0.0411(4) Uani 1 1 d . . .
C22 C 0.38675(17) 0.57201(17) -0.06340(16) 0.0413(4) Uani 1 1 d . . .
O2 O -0.00687(17) -0.55527(16) -0.41313(16) 0.0692(5) Uani 1 1 d . . .
C8 C 0.0889(2) -0.3109(2) -0.18984(17) 0.0475(4) Uani 1 1 d . . .
H8A H 0.1513 -0.3313 -0.2257 0.071 Uiso 1 1 calc R . .
H8B H 0.0394 -0.3859 -0.1826 0.071 Uiso 1 1 calc R . .
H8C H 0.1328 -0.2299 -0.1139 0.071 Uiso 1 1 calc R . .
C19 C 0.53925(17) 0.5802(2) -0.20268(17) 0.0459(4) Uani 1 1 d . . .
C21 C 0.4534(2) 0.6944(2) -0.0570(2) 0.0538(5) Uani 1 1 d . . .
H21 H 0.4469 0.7734 -0.0064 0.065 Uiso 1 1 calc R . .
O3 O -0.20664(18) -0.62407(16) -0.4270(2) 0.0868(6) Uani 1 1 d . . .
C24 C 0.26315(19) -0.04012(19) -0.28983(19) 0.0492(5) Uani 1 1 d . . .
O8 O -0.2184(2) -0.1805(3) -0.5289(2) 0.1095(8) Uani 1 1 d . . .
C7 C -0.2787(2) -0.5075(2) -0.55807(19) 0.0598(6) Uani 1 1 d . . .
H7A H -0.3569 -0.5487 -0.5459 0.090 Uiso 1 1 calc R . .
H7B H -0.2442 -0.5732 -0.5904 0.090 Uiso 1 1 calc R . .
H7C H -0.2969 -0.4775 -0.6111 0.090 Uiso 1 1 calc R . .
O9 O -0.36838(18) -0.2669(2) -0.4779(2) 0.0962(7) Uani 1 1 d . . .
C20 C 0.5284(2) 0.6974(2) -0.1258(2) 0.0551(5) Uani 1 1 d . . .
H20 H 0.5733 0.7794 -0.1215 0.066 Uiso 1 1 calc R . .
C23 C 0.6219(2) 0.5846(3) -0.2784(2) 0.0627(6) Uani 1 1 d . . .
H23A H 0.7080 0.6536 -0.2305 0.094 Uiso 1 1 calc R . .
H23B H 0.5865 0.6058 -0.3330 0.094 Uiso 1 1 calc R . .
H23C H 0.6239 0.4974 -0.3202 0.094 Uiso 1 1 calc R . .
N4 N 0.80845(17) 0.13543(17) -0.26554(15) 0.0508(4) Uani 1 1 d . . .
C30 C 0.9968(3) 0.2382(4) -0.3169(3) 0.0957(10) Uani 1 1 d . . .
H30A H 0.9409 0.2077 -0.3922 0.144 Uiso 1 1 calc R . .
H30B H 1.0254 0.1698 -0.3222 0.144 Uiso 1 1 calc R . .
H30C H 1.0702 0.3217 -0.2911 0.144 Uiso 1 1 calc R . .
C29 C 0.9240(2) 0.2625(2) -0.2308(3) 0.0713(7) Uani 1 1 d . . .
H29A H 0.9816 0.2957 -0.1545 0.086 Uiso 1 1 calc R . .
H29B H 0.8963 0.3324 -0.2251 0.086 Uiso 1 1 calc R . .
C27 C 0.7002(2) 0.0931(2) -0.3677(2) 0.0639(6) Uani 1 1 d . . .
H27A H 0.6384 0.0008 -0.3956 0.077 Uiso 1 1 calc R . .
H27B H 0.7342 0.0911 -0.4297 0.077 Uiso 1 1 calc R . .
C25 C 0.7708(3) 0.1502(3) -0.1601(2) 0.0748(7) Uani 1 1 d . . .
H25A H 0.7404 0.2213 -0.1339 0.090 Uiso 1 1 calc R . .
H25B H 0.8464 0.1784 -0.0977 0.090 Uiso 1 1 calc R . .
C28 C 0.6305(2) 0.1827(3) -0.3443(3) 0.0696(7) Uani 1 1 d . . .
H28A H 0.5682 0.1534 -0.4160 0.104 Uiso 1 1 calc R . .
H28B H 0.6914 0.2755 -0.3117 0.104 Uiso 1 1 calc R . .
H28C H 0.5870 0.1765 -0.2902 0.104 Uiso 1 1 calc R . .
C26 C 0.6668(3) 0.0196(4) -0.1840(3) 0.0967(10) Uani 1 1 d . . .
H26A H 0.5893 -0.0048 -0.2411 0.145 Uiso 1 1 calc R . .
H26B H 0.6499 0.0326 -0.1132 0.145 Uiso 1 1 calc R . .
H26C H 0.6949 -0.0521 -0.2130 0.145 Uiso 1 1 calc R . .
H1A H 0.099(2) 0.303(2) 0.059(2) 0.054(6) Uiso 1 1 d . . .
H4 H 0.840(2) 0.072(3) -0.284(2) 0.066(7) Uiso 1 1 d . . .
H1B H 0.062(3) 0.150(3) 0.015(2) 0.084(8) 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
O6 C10 1.362(2) . ?
O6 C22 1.389(2) . ?
C16 C17 1.463(2) . ?
C16 C11 1.404(2) . ?
C16 C15 1.388(2) . ?
C13 C12 1.423(2) . ?
C13 C14 1.394(2) . ?
C13 C9 1.514(2) . ?
O4 C1 1.2686(19) . ?
C12 C11 1.427(2) . ?
C12 N1 1.347(2) . ?
C14 C15 1.389(2) . ?
C14 C24 1.510(2) . ?
C17 C18 1.397(2) . ?
C17 C22 1.382(2) . ?
C6 C1 1.430(2) . ?
C6 C9 1.480(2) . ?
C6 C5 1.399(2) . ?
C11 C10 1.461(2) . ?
C1 C2 1.425(2) . ?
O7 C10 1.206(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(2) . ?
C9 O5 1.218(2) . ?
C15 H15 0.9300 . ?
F1 C24 1.338(2) . ?
N1 H1A 0.93(2) . ?
N1 H1B 0.88(3) . ?
C5 C4 1.396(2) . ?
C5 C8 1.512(2) . ?
F3 C24 1.320(2) . ?
C3 C2 1.370(2) . ?
C3 C4 1.397(2) . ?
C3 C7 1.503(3) . ?
N2 C2 1.468(2) . ?
N2 O8 1.195(3) . ?
N2 O9 1.201(3) . ?
C4 N3 1.465(2) . ?
F2 C24 1.338(3) . ?
N3 O2 1.221(2) . ?
N3 O3 1.219(2) . ?
C22 C21 1.388(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C19 C20 1.396(3) . ?
C19 C23 1.503(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.364(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C20 H20 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N4 C29 1.498(3) . ?
N4 C27 1.489(3) . ?
N4 C25 1.503(3) . ?
N4 H4 0.91(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30 C29 1.511(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.496(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.507(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O6 C22 122.62(13) . . ?
C11 C16 C17 119.31(14) . . ?
C15 C16 C17 121.42(15) . . ?
C15 C16 C11 119.27(14) . . ?
C12 C13 C9 117.56(14) . . ?
C14 C13 C12 118.72(14) . . ?
C14 C13 C9 123.66(14) . . ?
C13 C12 C11 118.69(14) . . ?
N1 C12 C13 120.48(14) . . ?
N1 C12 C11 120.80(15) . . ?
C13 C14 C24 121.70(14) . . ?
C15 C14 C13 122.01(14) . . ?
C15 C14 C24 116.29(15) . . ?
C18 C17 C16 124.78(15) . . ?
C22 C17 C16 118.25(15) . . ?
C22 C17 C18 116.97(15) . . ?
C1 C6 C9 115.17(13) . . ?
C5 C6 C1 121.79(14) . . ?
C5 C6 C9 123.03(14) . . ?
C16 C11 C12 120.85(14) . . ?
C16 C11 C10 119.92(14) . . ?
C12 C11 C10 119.23(15) . . ?
O4 C1 C6 121.74(14) . . ?
O4 C1 C2 122.91(14) . . ?
C2 C1 C6 115.31(14) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.50(17) . . ?
C19 C18 H18 118.8 . . ?
C6 C9 C13 119.43(13) . . ?
O5 C9 C13 118.40(14) . . ?
O5 C9 C6 122.14(15) . . ?
C16 C15 C14 120.45(15) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C12 N1 H1A 120.8(14) . . ?
C12 N1 H1B 121.2(19) . . ?
H1A N1 H1B 118(2) . . ?
C6 C5 C8 122.04(15) . . ?
C4 C5 C6 117.44(14) . . ?
C4 C5 C8 120.51(14) . . ?
C2 C3 C4 115.33(15) . . ?
C2 C3 C7 121.62(17) . . ?
C4 C3 C7 122.99(16) . . ?
O8 N2 C2 118.88(19) . . ?
O8 N2 O9 122.1(2) . . ?
O9 N2 C2 118.9(2) . . ?
C1 C2 N2 114.83(14) . . ?
C3 C2 C1 125.44(15) . . ?
C3 C2 N2 119.70(15) . . ?
C5 C4 C3 124.64(14) . . ?
C5 C4 N3 118.15(15) . . ?
C3 C4 N3 117.21(15) . . ?
O2 N3 C4 118.85(16) . . ?
O3 N3 C4 118.39(16) . . ?
O3 N3 O2 122.75(17) . . ?
O6 C10 C11 118.23(15) . . ?
O7 C10 O6 115.01(15) . . ?
O7 C10 C11 126.76(16) . . ?
C17 C22 O6 121.67(15) . . ?
C17 C22 C21 122.13(18) . . ?
C21 C22 O6 116.19(16) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C18 C19 C20 117.78(17) . . ?
C18 C19 C23 121.19(19) . . ?
C20 C19 C23 121.03(18) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 C22 119.12(18) . . ?
C20 C21 H21 120.4 . . ?
F1 C24 C14 112.16(14) . . ?
F3 C24 C14 113.23(16) . . ?
F3 C24 F1 106.08(17) . . ?
F3 C24 F2 106.56(16) . . ?
F2 C24 C14 112.01(17) . . ?
F2 C24 F1 106.31(16) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.49(17) . . ?
C21 C20 H20 119.3 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 N4 C25 109.3(2) . . ?
C29 N4 H4 102.8(16) . . ?
C27 N4 C29 113.75(19) . . ?
C27 N4 C25 114.25(18) . . ?
C27 N4 H4 109.9(16) . . ?
C25 N4 H4 105.9(16) . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
N4 C29 C30 112.2(2) . . ?
N4 C29 H29A 109.2 . . ?
N4 C29 H29B 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
N4 C27 H27A 108.5 . . ?
N4 C27 H27B 108.5 . . ?
N4 C27 C28 115.0(2) . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
N4 C25 H25A 109.1 . . ?
N4 C25 H25B 109.1 . . ?
N4 C25 C26 112.6(2) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C22 C21 C20 179.13(18) . . . . ?
C16 C17 C18 C19 -179.67(16) . . . . ?
C16 C17 C22 O6 0.3(3) . . . . ?
C16 C17 C22 C21 179.54(17) . . . . ?
C16 C11 C10 O6 -0.4(2) . . . . ?
C16 C11 C10 O7 178.65(18) . . . . ?
C13 C12 C11 C16 -0.5(2) . . . . ?
C13 C12 C11 C10 179.29(15) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C13 C14 C24 F1 -162.97(16) . . . . ?
C13 C14 C24 F3 77.0(2) . . . . ?
C13 C14 C24 F2 -43.5(2) . . . . ?
O4 C1 C2 C3 -176.01(17) . . . . ?
O4 C1 C2 N2 2.0(3) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C12 C13 C14 C24 178.96(15) . . . . ?
C12 C13 C9 C6 124.30(16) . . . . ?
C12 C13 C9 O5 -54.1(2) . . . . ?
C12 C11 C10 O6 179.79(15) . . . . ?
C12 C11 C10 O7 -1.1(3) . . . . ?
C14 C13 C12 C11 0.6(2) . . . . ?
C14 C13 C12 N1 178.44(15) . . . . ?
C14 C13 C9 C6 -58.4(2) . . . . ?
C14 C13 C9 O5 123.22(18) . . . . ?
C17 C16 C11 C12 -179.30(14) . . . . ?
C17 C16 C11 C10 0.9(2) . . . . ?
C17 C16 C15 C14 179.17(15) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C17 C18 C19 C23 -179.65(17) . . . . ?
C17 C22 C21 C20 -0.2(3) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C1 C2 N2 179.77(15) . . . . ?
C6 C5 C4 C3 -1.5(2) . . . . ?
C6 C5 C4 N3 178.83(15) . . . . ?
C11 C16 C17 C18 178.32(15) . . . . ?
C11 C16 C17 C22 -0.9(2) . . . . ?
C11 C16 C15 C14 -0.6(2) . . . . ?
C1 C6 C9 C13 -45.2(2) . . . . ?
C1 C6 C9 O5 133.16(18) . . . . ?
C1 C6 C5 C4 2.5(2) . . . . ?
C1 C6 C5 C8 -178.33(15) . . . . ?
C18 C17 C22 O6 -178.95(15) . . . . ?
C18 C17 C22 C21 0.3(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C9 C13 C12 C11 178.06(14) . . . . ?
C9 C13 C12 N1 -4.1(2) . . . . ?
C9 C13 C14 C15 -178.04(15) . . . . ?
C9 C13 C14 C24 1.7(2) . . . . ?
C9 C6 C1 O4 -5.4(2) . . . . ?
C9 C6 C1 C2 176.84(15) . . . . ?
C9 C6 C5 C4 -176.86(15) . . . . ?
C9 C6 C5 C8 2.4(2) . . . . ?
C15 C16 C17 C18 -1.5(2) . . . . ?
C15 C16 C17 C22 179.35(16) . . . . ?
C15 C16 C11 C12 0.5(2) . . . . ?
C15 C16 C11 C10 -179.27(15) . . . . ?
C15 C14 C24 F1 16.8(2) . . . . ?
C15 C14 C24 F3 -103.27(18) . . . . ?
C15 C14 C24 F2 136.20(17) . . . . ?
N1 C12 C11 C16 -178.33(15) . . . . ?
N1 C12 C11 C10 1.4(2) . . . . ?
C5 C6 C1 O4 175.27(16) . . . . ?
C5 C6 C1 C2 -2.5(2) . . . . ?
C5 C6 C9 C13 134.18(16) . . . . ?
C5 C6 C9 O5 -47.5(2) . . . . ?
C5 C4 N3 O2 -55.5(2) . . . . ?
C5 C4 N3 O3 125.1(2) . . . . ?
C3 C4 N3 O2 124.79(19) . . . . ?
C3 C4 N3 O3 -54.6(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 N3 -179.62(16) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C4 C3 C2 N2 -178.80(16) . . . . ?
C10 O6 C22 C17 0.2(3) . . . . ?
C10 O6 C22 C21 -179.07(18) . . . . ?
C22 O6 C10 C11 -0.2(3) . . . . ?
C22 O6 C10 O7 -179.35(16) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C22 C21 C20 C19 0.2(3) . . . . ?
C8 C5 C4 C3 179.24(17) . . . . ?
C8 C5 C4 N3 -0.4(2) . . . . ?
C24 C14 C15 C16 -178.95(16) . . . . ?
O8 N2 C2 C1 72.4(3) . . . . ?
O8 N2 C2 C3 -109.4(2) . . . . ?
C7 C3 C2 C1 -178.07(18) . . . . ?
C7 C3 C2 N2 4.0(3) . . . . ?
C7 C3 C4 C5 177.88(18) . . . . ?
C7 C3 C4 N3 -2.5(3) . . . . ?
O9 N2 C2 C1 -104.7(2) . . . . ?
O9 N2 C2 C3 73.4(3) . . . . ?
C23 C19 C20 C21 179.8(2) . . . . ?
C29 N4 C27 C28 -71.3(3) . . . . ?
C29 N4 C25 C26 -172.1(2) . . . . ?
C27 N4 C29 C30 -72.1(2) . . . . ?
C27 N4 C25 C26 59.1(3) . . . . ?
C25 N4 C29 C30 158.94(19) . . . . ?
C25 N4 C27 C28 55.2(3) . . . . ?

####################################################################### 
# 
# 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_610
_database_code_depnum_ccdc_archive 'CCDC 1465067'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_audit_creation_date             2016-01-20
_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         'C23 H13 F3 N3 O8, C6 H16 N'
_chemical_formula_sum            'C29 H29 F3 N4 O8'
_chemical_formula_weight         618.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.6138(12)
_cell_length_b                   12.2004(5)
_cell_length_c                   14.8315(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.227(9)
_cell_angle_gamma                90.00
_cell_volume                     2928.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1521
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.2430
_cell_measurement_theta_min      2.3590
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14147
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.26
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -61.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920 -178.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00    0.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -97.00  -51.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920 -178.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   92.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920    0.0000  150.0000 130
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0140520000
_diffrn_orient_matrix_UB_12      0.0448809000
_diffrn_orient_matrix_UB_13      -0.0328311000
_diffrn_orient_matrix_UB_21      -0.0211676000
_diffrn_orient_matrix_UB_22      0.0212146000
_diffrn_orient_matrix_UB_23      0.0281552000
_diffrn_orient_matrix_UB_31      0.0357053000
_diffrn_orient_matrix_UB_32      0.0302472000
_diffrn_orient_matrix_UB_33      0.0289383000
_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                3173
_reflns_number_total             7256
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         7256
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.000
_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)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1832
_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
O2 O 0.18859(13) 0.36215(15) 0.39426(15) 0.0677(6) Uani 1 1 d . . .
O1 O 0.11029(10) 0.50765(15) 0.34020(13) 0.0541(5) Uani 1 1 d . . .
O3 O 0.27160(11) 0.54491(14) 0.20941(14) 0.0576(5) Uani 1 1 d . . .
N2 N 0.10853(14) 0.5456(2) 0.08749(17) 0.0518(6) Uani 1 1 d . . .
C2 C 0.27914(15) 0.73866(19) 0.21972(18) 0.0408(6) Uani 1 1 d . . .
C1 C 0.23655(15) 0.6385(2) 0.18597(18) 0.0427(6) Uani 1 1 d . . .
C5 C 0.10885(15) 0.7468(2) 0.09743(17) 0.0433(6) Uani 1 1 d . . .
C16 C 0.24643(15) 0.6444(2) 0.43499(18) 0.0421(6) Uani 1 1 d . . .
C6 C 0.15138(15) 0.6493(2) 0.12420(18) 0.0415(6) Uani 1 1 d . . .
C15 C 0.25435(15) 0.5336(2) 0.43994(19) 0.0443(6) Uani 1 1 d . . .
C3 C 0.24056(17) 0.8400(2) 0.19171(18) 0.0455(6) Uani 1 1 d . . .
C14 C 0.18448(17) 0.4604(2) 0.39205(19) 0.0501(7) Uani 1 1 d . . .
N1 N 0.11549(18) 0.9476(2) 0.1041(2) 0.0609(7) Uani 1 1 d . . .
C9 C 0.36986(16) 0.7308(2) 0.2830(2) 0.0473(7) Uani 1 1 d . . .
C4 C 0.15679(17) 0.8408(2) 0.13219(19) 0.0462(6) Uani 1 1 d . B .
C22 C 0.10003(16) 0.6198(2) 0.33701(19) 0.0465(7) Uani 1 1 d . . .
F1 F 0.4464(3) 0.8966(3) 0.4533(4) 0.1020(16) Uani 0.90 1 d P A 1
C23 C 0.33103(19) 0.4798(2) 0.4940(2) 0.0595(8) Uani 1 1 d . . .
O5 O 0.05737(14) 0.5144(2) 0.11754(17) 0.0808(7) Uani 1 1 d . . .
O6 O 0.12807(13) 0.49352(18) 0.02989(17) 0.0782(7) Uani 1 1 d . . .
C17 C 0.16570(16) 0.6901(2) 0.38300(19) 0.0440(6) Uani 1 1 d . . .
C11 C 0.38138(15) 0.7308(2) 0.45836(18) 0.0448(7) Uani 1 1 d . A .
C10 C 0.39547(15) 0.6687(2) 0.37870(18) 0.0469(7) Uani 1 1 d . . .
H10A H 0.3648 0.6004 0.3669 0.056 Uiso 1 1 calc R . .
H10B H 0.4537 0.6506 0.4013 0.056 Uiso 1 1 calc R . .
C13 C 0.31685(17) 0.7193(2) 0.48293(19) 0.0485(7) Uani 1 1 d . . .
H13 H 0.3160 0.7618 0.5346 0.058 Uiso 1 1 calc R . .
N1A N 0.31222(17) 0.3546(2) 0.1456(2) 0.0614(7) Uani 1 1 d . . .
C21 C 0.02095(17) 0.6571(3) 0.2843(2) 0.0604(8) Uani 1 1 d . . .
H21 H -0.0221 0.6082 0.2538 0.073 Uiso 1 1 calc R . .
O4 O 0.42037(12) 0.7728(2) 0.25868(17) 0.0835(7) Uani 1 1 d . . .
C18 C 0.14926(19) 0.8028(2) 0.3756(2) 0.0568(8) Uani 1 1 d . . .
H18 H 0.1920 0.8524 0.4056 0.068 Uiso 1 1 calc R . .
C8 C 0.2875(2) 0.9450(2) 0.2287(2) 0.0704(9) Uani 1 1 d . . .
H8A H 0.3326 0.9317 0.2905 0.106 Uiso 1 1 calc R . .
H8B H 0.2513 0.9990 0.2372 0.106 Uiso 1 1 calc R . .
H8C H 0.3087 0.9711 0.1821 0.106 Uiso 1 1 calc R . .
O9 O 0.1424(4) 1.0126(6) 0.0607(6) 0.0753(17) Uani 0.70 1 d P B 1
F2 F 0.4373(3) 0.8600(4) 0.5868(3) 0.1082(17) Uani 0.90 1 d P A 1
C7 C 0.01814(16) 0.7511(2) 0.0330(2) 0.0621(8) Uani 1 1 d . . .
H7A H 0.0021 0.6844 -0.0041 0.093 Uiso 1 1 calc R . .
H7B H 0.0074 0.8122 -0.0111 0.093 Uiso 1 1 calc R . .
H7C H -0.0130 0.7593 0.0731 0.093 Uiso 1 1 calc R . .
C12 C 0.4453(2) 0.8147(3) 0.5114(3) 0.0640(9) Uani 1 1 d . . .
O10 O 0.0530(2) 0.9658(3) 0.1205(3) 0.0758(10) Uani 0.70 1 d P B 1
F3 F 0.52162(19) 0.7731(4) 0.5444(3) 0.1133(14) Uani 0.90 1 d P A 1
C20 C 0.0072(2) 0.7683(3) 0.2780(2) 0.0698(9) Uani 1 1 d . . .
H20 H -0.0456 0.7950 0.2419 0.084 Uiso 1 1 calc R . .
N3 N 0.39111(18) 0.4346(2) 0.5365(2) 0.0912(10) Uani 1 1 d . . .
C19 C 0.0705(2) 0.8405(3) 0.3243(2) 0.0673(9) Uani 1 1 d . . .
H19 H 0.0599 0.9154 0.3210 0.081 Uiso 1 1 calc R . .
C7A C 0.2039(3) 0.2640(3) 0.1905(3) 0.0929(12) Uani 1 1 d . . .
H7AA H 0.1452 0.2618 0.1542 0.139 Uiso 0.75 1 calc PR C 1
H7AB H 0.2182 0.3279 0.2316 0.139 Uiso 0.75 1 calc PR C 1
H7AC H 0.2213 0.1995 0.2305 0.139 Uiso 0.75 1 calc PR C 1
H7AD H 0.1760 0.2634 0.1203 0.139 Uiso 0.25 1 calc PR C 2
H7AE H 0.1843 0.3244 0.2167 0.139 Uiso 0.25 1 calc PR C 2
H7AF H 0.1932 0.1965 0.2166 0.139 Uiso 0.25 1 calc PR C 2
C3A C 0.2464(3) 0.2684(3) 0.1202(3) 0.0709(12) Uani 0.75 1 d P D 1
H3AA H 0.2710 0.1975 0.1194 0.085 Uiso 0.75 1 calc PR D 1
H3AB H 0.2055 0.2825 0.0547 0.085 Uiso 0.75 1 calc PR D 1
C8A C 0.4465(2) 0.4242(4) 0.2693(4) 0.132(2) Uani 1 1 d . . .
H8AA H 0.4470 0.4607 0.2122 0.198 Uiso 0.75 1 calc PR D 1
H8AB H 0.5005 0.3953 0.3070 0.198 Uiso 0.75 1 calc PR D 1
H8AC H 0.4314 0.4755 0.3085 0.198 Uiso 0.75 1 calc PR D 1
H8AD H 0.4561 0.4979 0.2536 0.198 Uiso 0.25 1 calc PR D 2
H8AE H 0.4985 0.3886 0.3043 0.198 Uiso 0.25 1 calc PR D 2
H8AF H 0.4151 0.4256 0.3094 0.198 Uiso 0.25 1 calc PR D 2
C1A C 0.3839(4) 0.3308(5) 0.2377(5) 0.106(2) Uani 0.75 1 d P D 1
H1AA H 0.4110 0.2648 0.2291 0.128 Uiso 0.75 1 calc PR D 1
H1AB H 0.3644 0.3169 0.2894 0.128 Uiso 0.75 1 calc PR D 1
C9A C 0.2821(4) 0.4038(4) -0.0268(4) 0.144(2) Uani 1 1 d . . .
H9AA H 0.2896 0.3701 -0.0812 0.216 Uiso 0.75 1 calc PR D 1
H9AB H 0.2890 0.4817 -0.0290 0.216 Uiso 0.75 1 calc PR D 1
H9AC H 0.2275 0.3882 -0.0305 0.216 Uiso 0.75 1 calc PR D 1
H9AD H 0.2502 0.3819 -0.0933 0.216 Uiso 0.25 1 calc PR D 2
H9AE H 0.3395 0.4065 -0.0159 0.216 Uiso 0.25 1 calc PR D 2
H9AF H 0.2643 0.4750 -0.0155 0.216 Uiso 0.25 1 calc PR D 2
C2A C 0.3415(5) 0.3617(5) 0.0625(5) 0.119(2) Uani 0.75 1 d P D 1
H2AA H 0.3902 0.4078 0.0832 0.142 Uiso 0.75 1 calc PR D 1
H2AB H 0.3576 0.2890 0.0503 0.142 Uiso 0.75 1 calc PR D 1
C4A C 0.2905(9) 0.2753(12) 0.2167(11) 0.085(4) Uani 0.25 1 d PU D 2
H4AA H 0.3140 0.2036 0.2159 0.102 Uiso 0.25 1 calc PR D 2
H4AB H 0.3158 0.3035 0.2832 0.102 Uiso 0.25 1 calc PR D 2
C6A C 0.2698(9) 0.3231(12) 0.0419(10) 0.077(4) Uani 0.25 1 d PU D 2
H6AA H 0.2112 0.3159 0.0264 0.092 Uiso 0.25 1 calc PR D 2
H6AB H 0.2902 0.2522 0.0320 0.092 Uiso 0.25 1 calc PR D 2
C5A C 0.4010(10) 0.3647(15) 0.1796(14) 0.088(5) Uani 0.25 1 d PU D 2
H5AA H 0.4127 0.3992 0.1275 0.106 Uiso 0.25 1 calc PR D 2
H5AB H 0.4237 0.2912 0.1875 0.106 Uiso 0.25 1 calc PR D 2
O7 O 0.1107(8) 1.0008(8) 0.1738(8) 0.110(3) Uani 0.30 1 d PU B 2
O8 O 0.1099(12) 0.9878(18) 0.0338(16) 0.104(7) Uani 0.30 1 d PU B 2
H1A H 0.2909(18) 0.417(3) 0.154(2) 0.070(10) Uiso 1 1 d . . .
F3A F 0.5010(16) 0.777(2) 0.5852(17) 0.063(7) Uani 0.10 1 d PU A 2
F1A F 0.408(2) 0.884(3) 0.557(3) 0.097(12) Uani 0.10 1 d PU A 2
F2A F 0.475(2) 0.859(3) 0.461(3) 0.077(10) Uani 0.10 1 d PU 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
O2 C14 1.201(3) . ?
O1 C14 1.356(3) . ?
O1 C22 1.378(3) . ?
O3 C1 1.279(3) . ?
N2 C6 1.464(3) . ?
N2 O5 1.213(3) . ?
N2 O6 1.218(3) . ?
C2 C1 1.418(3) . ?
C2 C3 1.393(3) . ?
C2 C9 1.503(3) . ?
C1 C6 1.422(3) . ?
C5 C6 1.378(3) . ?
C5 C4 1.396(4) . ?
C5 C7 1.505(3) . ?
C16 C15 1.358(3) . ?
C16 C17 1.436(4) . ?
C16 C13 1.477(4) . ?
C15 C14 1.458(4) . ?
C15 C23 1.430(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.506(4) . ?
N1 C4 1.470(3) . ?
N1 O9 1.228(9) . ?
N1 O10 1.237(4) . ?
N1 O7 1.250(10) . ?
N1 O8 1.12(2) . ?
C9 C10 1.513(4) . ?
C9 O4 1.199(3) . ?
C22 C17 1.385(4) . ?
C22 C21 1.378(4) . ?
F1 C12 1.325(5) . ?
C23 N3 1.138(3) . ?
C17 C18 1.401(4) . ?
C11 C10 1.505(4) . ?
C11 C13 1.331(4) . ?
C11 C12 1.495(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13 0.9300 . ?
N1A C3A 1.498(5) . ?
N1A C1A 1.478(6) . ?
N1A C2A 1.515(6) . ?
N1A C4A 1.585(16) . ?
N1A C6A 1.472(13) . ?
N1A C5A 1.447(16) . ?
N1A H1A 0.88(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
F2 C12 1.305(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C12 F3 1.336(5) . ?
C12 F3A 1.23(2) . ?
C12 F1A 1.40(4) . ?
C12 F2A 1.19(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.374(4) . ?
C19 H19 0.9300 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C7A H7AD 0.9600 . ?
C7A H7AE 0.9600 . ?
C7A H7AF 0.9600 . ?
C7A C3A 1.505(5) . ?
C7A C4A 1.424(15) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C8A H8AD 0.9600 . ?
C8A H8AE 0.9600 . ?
C8A H8AF 0.9600 . ?
C8A C1A 1.526(7) . ?
C8A C5A 1.449(16) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C9A H9AD 0.9600 . ?
C9A H9AE 0.9600 . ?
C9A H9AF 0.9600 . ?
C9A C2A 1.422(7) . ?
C9A C6A 1.492(17) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?

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
C14 O1 C22 121.7(2) . . ?
O5 N2 C6 118.9(3) . . ?
O5 N2 O6 123.4(3) . . ?
O6 N2 C6 117.7(2) . . ?
C1 C2 C9 116.7(2) . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 C9 121.1(2) . . ?
O3 C1 C2 122.8(2) . . ?
O3 C1 C6 122.1(2) . . ?
C2 C1 C6 115.1(2) . . ?
C6 C5 C4 114.9(2) . . ?
C6 C5 C7 122.2(2) . . ?
C4 C5 C7 122.9(2) . . ?
C15 C16 C17 118.3(2) . . ?
C15 C16 C13 122.7(2) . . ?
C17 C16 C13 119.0(2) . . ?
C1 C6 N2 114.7(2) . . ?
C5 C6 N2 119.8(2) . . ?
C5 C6 C1 125.5(2) . . ?
C16 C15 C14 122.3(2) . . ?
C16 C15 C23 122.8(2) . . ?
C23 C15 C14 115.0(2) . . ?
C2 C3 C8 120.8(2) . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 C8 121.3(2) . . ?
O2 C14 O1 118.3(2) . . ?
O2 C14 C15 124.6(3) . . ?
O1 C14 C15 117.1(2) . . ?
O9 N1 C4 118.0(5) . . ?
O9 N1 O10 123.0(5) . . ?
O9 N1 O7 105.3(7) . . ?
O10 N1 C4 118.8(3) . . ?
O10 N1 O7 52.4(6) . . ?
O7 N1 C4 114.4(5) . . ?
O8 N1 C4 120.2(12) . . ?
O8 N1 O9 30.8(10) . . ?
O8 N1 O10 110.2(12) . . ?
O8 N1 O7 122.1(13) . . ?
C2 C9 C10 117.9(2) . . ?
O4 C9 C2 121.1(2) . . ?
O4 C9 C10 121.0(2) . . ?
C5 C4 N1 117.6(2) . . ?
C3 C4 C5 124.4(2) . . ?
C3 C4 N1 118.0(2) . . ?
O1 C22 C17 121.7(2) . . ?
C21 C22 O1 115.9(2) . . ?
C21 C22 C17 122.4(3) . . ?
N3 C23 C15 178.3(3) . . ?
C22 C17 C16 118.8(2) . . ?
C22 C17 C18 117.6(2) . . ?
C18 C17 C16 123.6(3) . . ?
C13 C11 C10 125.8(2) . . ?
C13 C11 C12 118.4(3) . . ?
C12 C11 C10 115.8(2) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 C9 113.8(2) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C16 C13 H13 117.3 . . ?
C11 C13 C16 125.4(2) . . ?
C11 C13 H13 117.3 . . ?
C3A N1A C2A 108.2(4) . . ?
C3A N1A C4A 51.2(5) . . ?
C3A N1A H1A 108.3(19) . . ?
C1A N1A C3A 112.9(4) . . ?
C1A N1A C2A 108.9(5) . . ?
C1A N1A C4A 66.9(6) . . ?
C1A N1A H1A 107.2(19) . . ?
C2A N1A C4A 145.6(6) . . ?
C2A N1A H1A 111(2) . . ?
C4A N1A H1A 102(2) . . ?
C6A N1A C3A 62.0(7) . . ?
C6A N1A C1A 144.2(6) . . ?
C6A N1A C2A 50.1(7) . . ?
C6A N1A C4A 112.4(9) . . ?
C6A N1A H1A 108(2) . . ?
C5A N1A C3A 140.4(8) . . ?
C5A N1A C1A 44.2(7) . . ?
C5A N1A C2A 67.1(8) . . ?
C5A N1A C4A 109.4(10) . . ?
C5A N1A C6A 114.8(10) . . ?
C5A N1A H1A 110(2) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 C22 118.4(3) . . ?
C20 C21 H21 120.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
F1 C12 C11 112.1(3) . . ?
F1 C12 F3 104.7(4) . . ?
F1 C12 F1A 89.3(19) . . ?
F2 C12 F1 105.8(4) . . ?
F2 C12 C11 115.3(3) . . ?
F2 C12 F3 106.2(4) . . ?
F2 C12 F1A 25.8(15) . . ?
F3 C12 C11 111.9(3) . . ?
F3 C12 F1A 130.7(14) . . ?
F3A C12 F1 130.3(14) . . ?
F3A C12 C11 112.5(14) . . ?
F3A C12 F2 73.3(13) . . ?
F3A C12 F3 37.0(12) . . ?
F3A C12 F1A 99.1(19) . . ?
F1A C12 C11 105.4(17) . . ?
F2A C12 F1 29.6(18) . . ?
F2A C12 C11 113.6(18) . . ?
F2A C12 F2 124.6(18) . . ?
F2A C12 F3 77.3(18) . . ?
F2A C12 F3A 110(2) . . ?
F2A C12 F1A 116(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AA C7A H7AD 54.1 . . ?
H7AA C7A H7AE 76.6 . . ?
H7AA C7A H7AF 82.1 . . ?
H7AB C7A H7AC 109.5 . . ?
H7AB C7A H7AD 126.1 . . ?
H7AB C7A H7AE 33.4 . . ?
H7AB C7A H7AF 118.9 . . ?
H7AC C7A H7AD 124.5 . . ?
H7AC C7A H7AE 117.1 . . ?
H7AC C7A H7AF 27.5 . . ?
H7AD C7A H7AE 109.5 . . ?
H7AD C7A H7AF 109.5 . . ?
H7AE C7A H7AF 109.5 . . ?
C3A C7A H7AA 109.5 . . ?
C3A C7A H7AB 109.5 . . ?
C3A C7A H7AC 109.5 . . ?
C3A C7A H7AD 55.4 . . ?
C3A C7A H7AE 127.7 . . ?
C3A C7A H7AF 122.8 . . ?
C4A C7A H7AA 163.2 . . ?
C4A C7A H7AB 76.3 . . ?
C4A C7A H7AC 82.2 . . ?
C4A C7A H7AD 109.5 . . ?
C4A C7A H7AE 109.5 . . ?
C4A C7A H7AF 109.5 . . ?
C4A C7A C3A 54.2(6) . . ?
N1A C3A C7A 113.4(3) . . ?
N1A C3A H3AA 108.9 . . ?
N1A C3A H3AB 108.9 . . ?
C7A C3A H3AA 108.9 . . ?
C7A C3A H3AB 108.9 . . ?
H3AA C3A H3AB 107.7 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AA C8A H8AD 44.7 . . ?
H8AA C8A H8AE 110.3 . . ?
H8AA C8A H8AF 138.4 . . ?
H8AB C8A H8AC 109.5 . . ?
H8AB C8A H8AD 104.9 . . ?
H8AB C8A H8AE 5.5 . . ?
H8AB C8A H8AF 109.0 . . ?
H8AC C8A H8AD 69.7 . . ?
H8AC C8A H8AE 113.6 . . ?
H8AC C8A H8AF 41.2 . . ?
H8AD C8A H8AE 109.5 . . ?
H8AD C8A H8AF 109.5 . . ?
H8AE C8A H8AF 109.5 . . ?
C1A C8A H8AA 109.5 . . ?
C1A C8A H8AB 109.5 . . ?
C1A C8A H8AC 109.5 . . ?
C1A C8A H8AD 143.2 . . ?
C1A C8A H8AE 104.3 . . ?
C1A C8A H8AF 71.3 . . ?
C5A C8A H8AA 67.4 . . ?
C5A C8A H8AB 114.4 . . ?
C5A C8A H8AC 134.3 . . ?
C5A C8A H8AD 109.5 . . ?
C5A C8A H8AE 109.5 . . ?
C5A C8A H8AF 109.5 . . ?
C5A C8A C1A 43.4(8) . . ?
N1A C1A C8A 112.8(5) . . ?
N1A C1A H1AA 109.0 . . ?
N1A C1A H1AB 109.0 . . ?
C8A C1A H1AA 109.0 . . ?
C8A C1A H1AB 109.0 . . ?
H1AA C1A H1AB 107.8 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AA C9A H9AD 40.2 . . ?
H9AA C9A H9AE 70.8 . . ?
H9AA C9A H9AF 134.1 . . ?
H9AB C9A H9AC 109.5 . . ?
H9AB C9A H9AD 105.8 . . ?
H9AB C9A H9AE 80.3 . . ?
H9AB C9A H9AF 33.4 . . ?
H9AC C9A H9AD 73.7 . . ?
H9AC C9A H9AE 168.8 . . ?
H9AC C9A H9AF 78.6 . . ?
H9AD C9A H9AE 109.5 . . ?
H9AD C9A H9AF 109.5 . . ?
H9AE C9A H9AF 109.5 . . ?
C2A C9A H9AA 109.5 . . ?
C2A C9A H9AB 109.5 . . ?
C2A C9A H9AC 109.5 . . ?
C2A C9A H9AD 140.6 . . ?
C2A C9A H9AE 61.0 . . ?
C2A C9A H9AF 109.6 . . ?
C2A C9A C6A 51.4(6) . . ?
C6A C9A H9AA 113.3 . . ?
C6A C9A H9AB 137.0 . . ?
C6A C9A H9AC 59.8 . . ?
C6A C9A H9AD 109.5 . . ?
C6A C9A H9AE 109.5 . . ?
C6A C9A H9AF 109.5 . . ?
N1A C2A H2AA 108.6 . . ?
N1A C2A H2AB 108.6 . . ?
C9A C2A N1A 114.7(5) . . ?
C9A C2A H2AA 108.6 . . ?
C9A C2A H2AB 108.6 . . ?
H2AA C2A H2AB 107.6 . . ?
N1A C4A H4AA 109.0 . . ?
N1A C4A H4AB 109.0 . . ?
C7A C4A N1A 113.0(9) . . ?
C7A C4A H4AA 109.0 . . ?
C7A C4A H4AB 109.0 . . ?
H4AA C4A H4AB 107.8 . . ?
N1A C6A C9A 113.1(11) . . ?
N1A C6A H6AA 109.0 . . ?
N1A C6A H6AB 109.0 . . ?
C9A C6A H6AA 109.0 . . ?
C9A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
N1A C5A C8A 119.5(12) . . ?
N1A C5A H5AA 107.4 . . ?
N1A C5A H5AB 107.4 . . ?
C8A C5A H5AA 107.4 . . ?
C8A C5A H5AB 107.4 . . ?
H5AA C5A H5AB 107.0 . . ?

####################################################################### 
# 
# 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_exp_635
_database_code_depnum_ccdc_archive 'CCDC 1465073'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_audit_creation_date             2015-08-31
_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         'C21 H11 F3 N2 O6'
_chemical_formula_sum            'C21 H11 F3 N2 O6'
_chemical_formula_weight         444.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8312(6)
_cell_length_b                   6.5653(2)
_cell_length_c                   20.2552(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.187(4)
_cell_angle_gamma                90.00
_cell_volume                     1828.58(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1860
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.6950
_cell_measurement_theta_min      2.9430
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8783
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   50.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   54.00   93.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega   16.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   35.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000    0.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0243164000
_diffrn_orient_matrix_UB_12      -0.0892469000
_diffrn_orient_matrix_UB_13      -0.0126237000
_diffrn_orient_matrix_UB_21      -0.0450466000
_diffrn_orient_matrix_UB_22      0.0525337000
_diffrn_orient_matrix_UB_23      -0.0022231000
_diffrn_orient_matrix_UB_31      0.0064350000
_diffrn_orient_matrix_UB_32      0.0307932000
_diffrn_orient_matrix_UB_33      -0.0327997000
_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                2511
_reflns_number_total             4037
_reflns_odcompleteness_completeness 89.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.002
_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)+(0.0700P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1372
_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
O1 O 0.82090(11) 0.3188(2) 0.03465(7) 0.0594(4) Uani 1 1 d . . .
O2 O 0.46291(12) 1.1485(2) -0.06048(8) 0.0607(4) Uani 1 1 d . . .
C3 C 0.54144(13) 0.8608(3) -0.10464(9) 0.0414(4) Uani 1 1 d . . .
O4 O 0.64597(11) 1.1155(2) -0.05801(8) 0.0646(5) Uani 1 1 d . . .
O5 O 0.93624(10) 0.2486(2) -0.02724(7) 0.0598(4) Uani 1 1 d . . .
C6 C 0.72761(13) 0.8246(3) -0.09164(9) 0.0388(4) Uani 1 1 d . . .
F7 F 0.81480(11) 1.0463(2) -0.23842(7) 0.0806(5) Uani 1 1 d . . .
C8 C 0.97398(13) 0.4570(3) -0.11904(9) 0.0435(5) Uani 1 1 d . . .
C9 C 0.86990(13) 0.7588(3) -0.14802(10) 0.0407(4) Uani 1 1 d . . .
C10 C 0.83585(13) 0.5435(3) -0.05665(9) 0.0397(4) Uani 1 1 d . . .
F11 F 0.66910(9) 1.0259(2) -0.21502(7) 0.0709(4) Uani 1 1 d . . .
C12 C 0.63778(14) 0.9461(3) -0.08337(10) 0.0438(5) Uani 1 1 d . . .
N13 N 0.69600(15) 0.6176(4) 0.00149(10) 0.0587(5) Uani 1 1 d . . .
C14 C 0.76065(15) 1.0416(3) -0.18842(11) 0.0489(5) Uani 1 1 d . . .
C15 C 0.86082(14) 0.3693(3) -0.01338(10) 0.0468(5) Uani 1 1 d . . .
C16 C 0.78808(13) 0.8713(3) -0.14032(9) 0.0393(4) Uani 1 1 d . . .
C17 C 0.89348(12) 0.5912(3) -0.10760(9) 0.0388(4) Uani 1 1 d . . .
C18 C 0.75184(13) 0.6619(3) -0.04772(9) 0.0412(4) Uani 1 1 d . . .
C19 C 0.53045(14) 0.6749(3) -0.13788(10) 0.0437(5) Uani 1 1 d . . .
N20 N 0.42926(14) 0.4071(3) -0.19238(9) 0.0604(5) Uani 1 1 d . . .
C21 C 0.45693(15) 0.9650(3) -0.09078(10) 0.0490(5) Uani 1 1 d . . .
O22 O 0.50310(12) 0.3171(3) -0.20291(9) 0.0767(5) Uani 1 1 d . . .
C23 C 0.36570(16) 0.8820(4) -0.10803(12) 0.0597(6) Uani 1 1 d . . .
F24 F 0.76852(12) 1.22296(19) -0.16000(8) 0.0866(5) Uani 1 1 d . . .
C25 C 0.43900(14) 0.5991(3) -0.15610(10) 0.0487(5) Uani 1 1 d . . .
C26 C 1.03350(14) 0.4822(4) -0.16985(11) 0.0549(6) Uani 1 1 d . . .
H26 H 1.0252 0.5963 -0.1971 0.066 Uiso 1 1 calc R . .
C27 C 0.99042(14) 0.2859(3) -0.07954(10) 0.0510(5) Uani 1 1 d . . .
C28 C 0.35607(16) 0.7005(4) -0.14053(12) 0.0587(6) Uani 1 1 d . . .
O29 O 0.34776(13) 0.3440(3) -0.21060(11) 0.0983(7) Uani 1 1 d . . .
C30 C 1.10407(15) 0.3427(4) -0.18056(12) 0.0663(7) Uani 1 1 d . . .
H30 H 1.1431 0.3625 -0.2146 0.080 Uiso 1 1 calc R . .
C31 C 1.06062(17) 0.1429(4) -0.08948(13) 0.0683(7) Uani 1 1 d . . .
H31 H 1.0697 0.0289 -0.0622 0.082 Uiso 1 1 calc R . .
C32 C 1.11662(17) 0.1730(5) -0.14046(13) 0.0737(8) Uani 1 1 d . . .
H32 H 1.1638 0.0775 -0.1481 0.088 Uiso 1 1 calc R . .
H13A H 0.6482(17) 0.693(4) 0.0089(13) 0.074(8) Uiso 1 1 d . . .
H2 H 0.526(2) 1.170(5) -0.0537(17) 0.119(12) Uiso 1 1 d . . .
H13B H 0.7154(17) 0.520(4) 0.0269(12) 0.068(8) Uiso 1 1 d . . .
H19 H 0.5824(14) 0.600(3) -0.1437(9) 0.047(6) Uiso 1 1 d . . .
H23 H 0.3101(16) 0.950(3) -0.0961(11) 0.062(6) Uiso 1 1 d . . .
H28 H 0.2962(18) 0.646(4) -0.1535(12) 0.072(7) Uiso 1 1 d . . .
H9 H 0.9055(14) 0.800(3) -0.1843(10) 0.047(5) 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
O1 C15 1.215(2) . ?
O2 C21 1.350(3) . ?
O2 H2 0.88(3) . ?
C3 C12 1.467(3) . ?
C3 C19 1.394(3) . ?
C3 C21 1.409(3) . ?
O4 C12 1.225(2) . ?
O5 C15 1.363(2) . ?
O5 C27 1.384(2) . ?
C6 C12 1.501(3) . ?
C6 C16 1.394(3) . ?
C6 C18 1.408(3) . ?
F7 C14 1.323(2) . ?
C8 C17 1.458(2) . ?
C8 C26 1.395(3) . ?
C8 C27 1.384(3) . ?
C9 C16 1.374(2) . ?
C9 C17 1.389(3) . ?
C9 H9 0.97(2) . ?
C10 C15 1.459(3) . ?
C10 C17 1.406(3) . ?
C10 C18 1.426(2) . ?
F11 C14 1.326(2) . ?
N13 C18 1.357(3) . ?
N13 H13A 0.85(2) . ?
N13 H13B 0.85(2) . ?
C14 C16 1.505(3) . ?
C14 F24 1.322(2) . ?
C19 C25 1.372(3) . ?
C19 H19 0.890(19) . ?
N20 O22 1.218(2) . ?
N20 C25 1.458(3) . ?
N20 O29 1.220(2) . ?
C21 C23 1.384(3) . ?
C23 C28 1.361(3) . ?
C23 H23 0.94(2) . ?
C25 C28 1.391(3) . ?
C26 H26 0.9300 . ?
C26 C30 1.373(3) . ?
C27 C31 1.381(3) . ?
C28 H28 0.91(2) . ?
C30 H30 0.9300 . ?
C30 C32 1.379(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.370(3) . ?
C32 H32 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
C21 O2 H2 103(2) . . ?
C19 C3 C12 121.63(16) . . ?
C19 C3 C21 118.16(18) . . ?
C21 C3 C12 120.20(18) . . ?
C15 O5 C27 122.99(16) . . ?
C16 C6 C12 121.96(17) . . ?
C16 C6 C18 119.58(16) . . ?
C18 C6 C12 118.45(16) . . ?
C26 C8 C17 124.53(19) . . ?
C27 C8 C17 118.66(18) . . ?
C27 C8 C26 116.71(19) . . ?
C16 C9 C17 120.17(18) . . ?
C16 C9 H9 115.4(12) . . ?
C17 C9 H9 124.3(12) . . ?
C17 C10 C15 119.96(17) . . ?
C17 C10 C18 120.39(17) . . ?
C18 C10 C15 119.64(17) . . ?
C3 C12 C6 120.07(16) . . ?
O4 C12 C3 120.65(18) . . ?
O4 C12 C6 119.28(18) . . ?
C18 N13 H13A 121.3(17) . . ?
C18 N13 H13B 116.2(17) . . ?
H13A N13 H13B 122(2) . . ?
F7 C14 F11 106.58(18) . . ?
F7 C14 C16 112.89(17) . . ?
F11 C14 C16 111.62(17) . . ?
F24 C14 F7 106.58(18) . . ?
F24 C14 F11 106.10(17) . . ?
F24 C14 C16 112.60(17) . . ?
O1 C15 O5 115.50(18) . . ?
O1 C15 C10 126.55(19) . . ?
O5 C15 C10 117.94(17) . . ?
C6 C16 C14 119.51(17) . . ?
C9 C16 C6 121.77(18) . . ?
C9 C16 C14 118.62(17) . . ?
C9 C17 C8 121.33(17) . . ?
C9 C17 C10 119.58(17) . . ?
C10 C17 C8 119.01(17) . . ?
C6 C18 C10 118.40(16) . . ?
N13 C18 C6 120.76(18) . . ?
N13 C18 C10 120.83(19) . . ?
C3 C19 H19 120.2(12) . . ?
C25 C19 C3 119.78(18) . . ?
C25 C19 H19 119.8(12) . . ?
O22 N20 C25 118.27(18) . . ?
O22 N20 O29 123.2(2) . . ?
O29 N20 C25 118.56(19) . . ?
O2 C21 C3 120.83(19) . . ?
O2 C21 C23 118.40(18) . . ?
C23 C21 C3 120.8(2) . . ?
C21 C23 H23 119.8(13) . . ?
C28 C23 C21 120.4(2) . . ?
C28 C23 H23 119.8(13) . . ?
C19 C25 N20 118.78(18) . . ?
C19 C25 C28 121.6(2) . . ?
C28 C25 N20 119.62(19) . . ?
C8 C26 H26 119.2 . . ?
C30 C26 C8 121.6(2) . . ?
C30 C26 H26 119.2 . . ?
C8 C27 O5 121.16(18) . . ?
C31 C27 O5 116.02(19) . . ?
C31 C27 C8 122.8(2) . . ?
C23 C28 C25 119.2(2) . . ?
C23 C28 H28 121.3(15) . . ?
C25 C28 H28 119.4(16) . . ?
C26 C30 H30 120.2 . . ?
C26 C30 C32 119.5(2) . . ?
C32 C30 H30 120.2 . . ?
C27 C31 H31 120.8 . . ?
C32 C31 C27 118.4(2) . . ?
C32 C31 H31 120.8 . . ?
C30 C32 H32 119.5 . . ?
C31 C32 C30 121.0(2) . . ?
C31 C32 H32 119.5 . . ?

####################################################################### 
# 
# 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_614
_database_code_depnum_ccdc_archive 'CCDC 1465074'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_audit_creation_date             2015-08-24
_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         'C21 H8 Br2 F3 N2 O6, C6 H16 N'
_chemical_formula_sum            'C27 H24 Br2 F3 N3 O6'
_chemical_formula_weight         703.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C108 H96 Br8 F12 N12 O24 '
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.0863(13)
_cell_length_b                   12.0796(6)
_cell_length_c                   14.2137(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.926(10)
_cell_angle_gamma                90.00
_cell_volume                     2860.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.1700
_cell_measurement_theta_min      2.3460
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15490
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9439
_diffrn_measured_fraction_theta_max 0.9439
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   16.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   58.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  178.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   38.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   -5.00   22.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000  150.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0424184000
_diffrn_orient_matrix_UB_12      0.0048443000
_diffrn_orient_matrix_UB_13      0.0209124000
_diffrn_orient_matrix_UB_21      -0.0035070000
_diffrn_orient_matrix_UB_22      0.0581354000
_diffrn_orient_matrix_UB_23      -0.0076862000
_diffrn_orient_matrix_UB_31      -0.0003350000
_diffrn_orient_matrix_UB_32      0.0069590000
_diffrn_orient_matrix_UB_33      0.0493803000
_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                4051
_reflns_number_total             6767
_reflns_odcompleteness_completeness 94.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         6767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1659
_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
Br1 Br 0.12182(3) 0.92746(3) 0.02597(4) 0.06611(19) Uani 1 1 d . . .
O3 O 0.28553(16) 1.0387(2) 0.0909(3) 0.0599(8) Uani 1 1 d . . .
C23 C 0.3263(3) 0.7616(4) 0.0885(4) 0.0686(13) Uani 1 1 d . . .
H23A H 0.2697 0.7557 0.0456 0.082 Uiso 1 1 calc R . .
H23B H 0.3531 0.7935 0.0476 0.082 Uiso 1 1 calc R . .
C19 C 0.1463(2) 1.0797(3) 0.0248(3) 0.0418(8) Uani 1 1 d . . .
N3 N 0.3364(2) 0.8389(3) 0.1764(3) 0.0482(8) Uani 1 1 d . . .
O6 O 0.1832(3) 1.4775(3) 0.0884(3) 0.0951(14) Uani 1 1 d . . .
N2 N 0.1960(3) 1.4193(3) 0.0263(3) 0.0664(12) Uani 1 1 d . . .
Br2 Br 0.01286(4) 1.36578(5) -0.04955(4) 0.0848(2) Uani 1 1 d . . .
C17 C 0.2430(2) 1.2257(3) 0.0536(3) 0.0418(9) Uani 1 1 d . . .
C27 C 0.4220(3) 0.8641(4) 0.2414(4) 0.0736(14) Uani 1 1 d . . .
H27A H 0.4237 0.9080 0.2993 0.088 Uiso 1 1 calc R . .
H27B H 0.4497 0.7950 0.2678 0.088 Uiso 1 1 calc R . .
C20 C 0.0848(3) 1.1544(3) -0.0065(3) 0.0506(10) Uani 1 1 d . . .
H20 H 0.0320 1.1298 -0.0290 0.061 Uiso 1 1 calc R . .
O1 O 0.11557(17) 1.0016(2) -0.2237(2) 0.0561(7) Uani 1 1 d . . .
C18 C 0.2287(2) 1.1089(3) 0.0585(3) 0.0401(8) Uani 1 1 d . . .
C28 C 0.4663(3) 0.9241(5) 0.1884(5) 0.0919(19) Uani 1 1 d . . .
H28A H 0.4643 0.8821 0.1301 0.138 Uiso 1 1 calc R . .
H28B H 0.5212 0.9338 0.2343 0.138 Uiso 1 1 calc R . .
H28C H 0.4420 0.9952 0.1664 0.138 Uiso 1 1 calc R . .
O4 O 0.3523(2) 1.3432(3) 0.1395(3) 0.0872(12) Uani 1 1 d . . .
C16 C 0.3270(3) 1.2646(3) 0.0836(3) 0.0508(10) Uani 1 1 d . . .
C25 C 0.2915(4) 0.7989(4) 0.2381(4) 0.0731(15) Uani 1 1 d . . .
H25A H 0.3218 0.7399 0.2827 0.088 Uiso 1 1 calc R . .
H25B H 0.2406 0.7684 0.1925 0.088 Uiso 1 1 calc R . .
C9 C 0.0208(3) 1.1444(4) -0.2800(4) 0.0617(12) Uani 1 1 d . . .
H9 H -0.0196 1.0916 -0.2946 0.074 Uiso 1 1 calc R . .
C24 C 0.3591(4) 0.6482(4) 0.1214(5) 0.0908(19) Uani 1 1 d . . .
H24A H 0.3527 0.6044 0.0623 0.136 Uiso 1 1 calc R . .
H24B H 0.3305 0.6140 0.1582 0.136 Uiso 1 1 calc R . .
H24C H 0.4150 0.6532 0.1648 0.136 Uiso 1 1 calc R . .
O5 O 0.2205(3) 1.4535(3) -0.0362(3) 0.1015(15) Uani 1 1 d . . .
F1 F 0.50395(16) 1.2999(3) -0.0157(3) 0.0877(10) Uani 1 1 d . . .
F2 F 0.4231(2) 1.3760(2) -0.1521(2) 0.0879(10) Uani 1 1 d . . .
C14 C 0.3681(2) 1.2538(3) -0.0660(3) 0.0419(9) Uani 1 1 d . . .
C15 C 0.4299(3) 1.3391(4) -0.0612(4) 0.0578(11) Uani 1 1 d . . .
F3 F 0.4265(2) 1.4272(2) -0.0076(3) 0.0910(10) Uani 1 1 d . . .
C13 C 0.3107(3) 1.2310(3) -0.1549(3) 0.0440(9) Uani 1 1 d . . .
H13 H 0.3120 1.2699 -0.2108 0.053 Uiso 1 1 calc R . .
O2 O 0.1996(2) 0.8616(2) -0.1750(3) 0.0732(10) Uani 1 1 d . . .
N1 N 0.3955(3) 0.9472(3) -0.1015(4) 0.0741(12) Uani 1 1 d . . .
C7 C 0.0620(3) 1.3327(4) -0.2772(4) 0.0658(13) Uani 1 1 d . . .
H7 H 0.0487 1.4071 -0.2906 0.079 Uiso 1 1 calc R . .
C5 C 0.1622(2) 1.1897(3) -0.2181(3) 0.0432(9) Uani 1 1 d . . .
C22 C 0.1787(3) 1.2999(3) 0.0253(3) 0.0458(9) Uani 1 1 d . . .
C1 C 0.3781(2) 1.2047(3) 0.0358(3) 0.0473(9) Uani 1 1 d . . .
H1A H 0.4341 1.2089 0.0818 0.057 Uiso 1 1 calc R . .
H1B H 0.3630 1.1271 0.0267 0.057 Uiso 1 1 calc R . .
C2 C 0.1914(3) 0.9600(3) -0.1861(3) 0.0507(10) Uani 1 1 d . . .
C21 C 0.1009(3) 1.2674(3) -0.0049(3) 0.0509(10) Uani 1 1 d . . .
C11 C 0.3353(3) 0.9898(3) -0.1273(3) 0.0510(10) Uani 1 1 d . . .
C10 C 0.1008(3) 1.1130(3) -0.2406(3) 0.0479(9) Uani 1 1 d . . .
C6 C 0.1410(3) 1.3013(3) -0.2376(3) 0.0547(11) Uani 1 1 d . . .
H6 H 0.1810 1.3546 -0.2236 0.066 Uiso 1 1 calc R . .
C8 C 0.0020(3) 1.2545(5) -0.2973(4) 0.0719(14) Uani 1 1 d . . .
H8 H -0.0514 1.2767 -0.3228 0.086 Uiso 1 1 calc R . .
C4 C 0.2442(2) 1.1504(3) -0.1764(3) 0.0412(8) Uani 1 1 d . . .
C26 C 0.2760(5) 0.8885(4) 0.3022(5) 0.097(2) Uani 1 1 d . . .
H26A H 0.2452 0.9468 0.2585 0.145 Uiso 1 1 calc R . .
H26B H 0.3262 0.9177 0.3490 0.145 Uiso 1 1 calc R . .
H26C H 0.2467 0.8580 0.3397 0.145 Uiso 1 1 calc R . .
C3 C 0.2572(2) 1.0393(3) -0.1624(3) 0.0442(9) Uani 1 1 d . . .
H3 H 0.315(3) 0.901(4) 0.150(4) 0.066(14) 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
Br1 C19 1.893(4) . ?
O3 C18 1.273(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 N3 1.513(5) . ?
C23 C24 1.493(7) . ?
C19 C20 1.365(5) . ?
C19 C18 1.422(5) . ?
N3 C27 1.493(6) . ?
N3 C25 1.488(5) . ?
N3 H3 0.86(5) . ?
O6 N2 1.219(4) . ?
N2 O5 1.210(4) . ?
N2 C22 1.474(5) . ?
Br2 C21 1.887(4) . ?
C17 C18 1.440(5) . ?
C17 C16 1.486(6) . ?
C17 C22 1.397(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.485(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.394(6) . ?
O1 C2 1.359(5) . ?
O1 C10 1.375(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O4 C16 1.209(5) . ?
C16 C1 1.526(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.509(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(6) . ?
C9 C8 1.371(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
F1 C15 1.326(5) . ?
F2 C15 1.326(5) . ?
C14 C15 1.503(5) . ?
C14 C13 1.314(6) . ?
C14 C1 1.508(5) . ?
C15 F3 1.325(5) . ?
C13 H13 0.9300 . ?
C13 C4 1.485(5) . ?
O2 C2 1.201(5) . ?
N1 C11 1.128(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(6) . ?
C7 C8 1.382(7) . ?
C5 C10 1.385(6) . ?
C5 C6 1.399(5) . ?
C5 C4 1.446(5) . ?
C22 C21 1.361(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.461(6) . ?
C11 C3 1.433(6) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C4 C3 1.364(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H23A C23 H23B 107.7 . . ?
N3 C23 H23A 108.8 . . ?
N3 C23 H23B 108.8 . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C24 C23 N3 113.7(4) . . ?
C20 C19 Br1 118.8(3) . . ?
C20 C19 C18 124.0(3) . . ?
C18 C19 Br1 117.2(3) . . ?
C23 N3 H3 107(3) . . ?
C27 N3 C23 113.5(4) . . ?
C27 N3 H3 106(3) . . ?
C25 N3 C23 111.6(4) . . ?
C25 N3 C27 112.0(4) . . ?
C25 N3 H3 107(3) . . ?
O6 N2 C22 118.2(3) . . ?
O5 N2 O6 124.2(4) . . ?
O5 N2 C22 117.7(3) . . ?
C18 C17 C16 118.6(4) . . ?
C22 C17 C18 119.8(3) . . ?
C22 C17 C16 121.5(3) . . ?
N3 C27 H27A 108.6 . . ?
N3 C27 H27B 108.6 . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 N3 114.8(5) . . ?
C28 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(4) . . ?
C21 C20 H20 119.8 . . ?
C2 O1 C10 121.9(3) . . ?
O3 C18 C19 123.3(3) . . ?
O3 C18 C17 122.4(3) . . ?
C19 C18 C17 114.3(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C17 C16 C1 116.8(3) . . ?
O4 C16 C17 121.3(4) . . ?
O4 C16 C1 121.8(4) . . ?
N3 C25 H25A 108.9 . . ?
N3 C25 H25B 108.9 . . ?
N3 C25 C26 113.3(4) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C14 C1 114.6(4) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 C1 126.5(3) . . ?
F1 C15 C14 111.7(3) . . ?
F2 C15 F1 106.8(3) . . ?
F2 C15 C14 113.6(4) . . ?
F3 C15 F1 105.7(4) . . ?
F3 C15 F2 106.4(4) . . ?
F3 C15 C14 112.1(3) . . ?
C14 C13 H13 116.3 . . ?
C14 C13 C4 127.4(3) . . ?
C4 C13 H13 116.3 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C10 C5 C6 117.7(4) . . ?
C10 C5 C4 118.5(3) . . ?
C6 C5 C4 123.8(4) . . ?
C17 C22 N2 118.4(4) . . ?
C21 C22 N2 118.3(4) . . ?
C21 C22 C17 123.3(3) . . ?
C16 C1 H1A 109.2 . . ?
C16 C1 H1B 109.2 . . ?
C14 C1 C16 111.9(3) . . ?
C14 C1 H1A 109.2 . . ?
C14 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 C3 117.1(3) . . ?
O2 C2 O1 118.2(4) . . ?
O2 C2 C3 124.8(4) . . ?
C20 C21 Br2 117.9(3) . . ?
C22 C21 Br2 124.0(3) . . ?
C22 C21 C20 118.1(4) . . ?
N1 C11 C3 177.3(5) . . ?
O1 C10 C9 116.1(4) . . ?
O1 C10 C5 122.0(4) . . ?
C5 C10 C9 121.9(4) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C5 C4 C13 119.2(3) . . ?
C3 C4 C13 122.4(4) . . ?
C3 C4 C5 118.3(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 C3 C2 114.3(3) . . ?
C4 C3 C2 122.2(4) . . ?
C4 C3 C11 123.5(4) . . ?

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
-11 -8 18 0.1774 -10.9682 -7.9190 17.5752 -0.1361 -0.5570 0.8164
3 17 0 0.0663 3.3135 16.7959 0.4332 0.2310 0.9615 0.1372
-23 4 1 0.0610 -23.1728 4.4625 1.1896 -0.9365 0.3316 0.0976
22 -4 1 0.0639 22.2010 -4.2677 0.9463 0.9408 -0.3332 0.0096
-23 5 2 0.0579 -23.4257 4.5137 1.8663 -0.9328 0.3302 0.1314
-2 0 -18 0.1380 -2.1974 0.3578 -17.6521 -0.4606 0.1642 -0.8684
-22 -6 1 0.0672 -22.3771 -6.0918 1.0255 -0.9573 -0.2836 0.0157
9 -2 -20 0.1511 8.7530 -2.3439 -19.7571 -0.0532 -0.0151 -0.9949
21 6 1 0.0690 21.3506 6.2644 0.8725 0.9542 0.2826 0.0795
-11 1 20 0.1761 -11.3385 0.5541 19.9213 -0.0617 -0.0811 0.9914
-13 -14 0 0.0873 -12.5681 -14.3256 -0.1175 -0.6050 -0.7878 -0.1013
9 -3 -20 0.1515 8.7488 -3.2594 -19.5791 -0.0541 -0.0697 -0.9924
11 -1 -20 0.1526 10.8333 -1.1191 -19.9097 0.0377 0.0500 -0.9946
12 14 1 0.0663 11.9273 14.3337 1.2090 0.6007 0.7822 0.1555
-11 3 20 0.1778 -11.2703 3.0264 19.6041 -0.0534 0.0648 0.9929
16 -12 0 0.0739 16.4528 -11.9911 0.2997 0.6461 -0.7571 -0.0742
-2 6 -16 0.1526 -2.4143 6.0358 -16.3731 -0.4156 0.4852 -0.7657
-17 12 2 0.0820 -17.4828 12.0360 2.3767 -0.6336 0.7428 0.2070

####################################################################### 
# 
# 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_699
_database_code_depnum_ccdc_archive 'CCDC 1465075'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_audit_creation_date             2015-10-07
_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         'C23 H14 F3 N3 O8'
_chemical_formula_sum            'C23 H14 F3 N3 O8'
_chemical_formula_weight         517.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.5239(5)
_cell_length_b                   11.2068(6)
_cell_length_c                   20.6780(10)
_cell_angle_alpha                104.099(4)
_cell_angle_beta                 96.924(4)
_cell_angle_gamma                99.452(4)
_cell_volume                     2300.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2915
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.8790
_cell_measurement_theta_min      2.4420
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18751
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.8871
_diffrn_measured_fraction_theta_max 0.9960
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   21.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -95.00  -65.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360 -178.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00    0.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -35.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360 -178.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega  -40.00   43.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  -52.0000  -24.0000 83

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   60.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  -99.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  7 omega  -28.00   81.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360    0.0000 -180.0000 109
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0527412000
_diffrn_orient_matrix_UB_12      0.0514540000
_diffrn_orient_matrix_UB_13      0.0150204000
_diffrn_orient_matrix_UB_21      0.0312725000
_diffrn_orient_matrix_UB_22      -0.0381271000
_diffrn_orient_matrix_UB_23      0.0168354000
_diffrn_orient_matrix_UB_31      0.0323140000
_diffrn_orient_matrix_UB_32      -0.0183521000
_diffrn_orient_matrix_UB_33      -0.0278941000
_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                4559
_reflns_number_total             10110
_reflns_odcompleteness_completeness 88.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         10110
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1581
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.007
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1799
_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
O3A O 0.5472(2) 0.5624(2) 0.17089(11) 0.0634(6) Uani 1 1 d . . .
O1A O 0.2653(2) 1.0685(2) 0.00841(12) 0.0726(7) Uani 1 1 d . . .
C20A C 0.5997(3) 0.6857(3) 0.19690(14) 0.0470(7) Uani 1 1 d . . .
C16A C 0.5629(3) 0.8956(3) 0.20383(14) 0.0479(7) Uani 1 1 d . . .
O8A O 0.2936(2) 0.7085(2) 0.15079(11) 0.0732(7) Uani 1 1 d . . .
O4A O 0.7595(3) 0.5391(3) 0.23746(16) 0.0975(9) Uani 1 1 d . . .
C15A C 0.5235(3) 0.7663(3) 0.17816(13) 0.0442(7) Uani 1 1 d . . .
C18A C 0.7655(3) 0.8666(3) 0.26581(14) 0.0521(8) Uani 1 1 d . . .
C19A C 0.7170(3) 0.7369(3) 0.24245(14) 0.0510(8) Uani 1 1 d . . .
C17A C 0.6851(3) 0.9393(3) 0.24483(15) 0.0521(8) Uani 1 1 d . . .
C12A C 0.2738(3) 0.6095(3) 0.01355(14) 0.0481(7) Uani 1 1 d . A .
C13A C 0.4046(3) 0.6653(3) 0.05707(13) 0.0511(8) Uani 1 1 d . . .
H13C H 0.4465 0.7349 0.0419 0.061 Uiso 1 1 calc R . .
H13D H 0.4589 0.6026 0.0515 0.061 Uiso 1 1 calc R . .
C11A C 0.1933(3) 0.6735(3) -0.00974(15) 0.0563(8) Uani 1 1 d . . .
H11A H 0.1116 0.6288 -0.0332 0.068 Uiso 1 1 calc R . .
C14A C 0.3967(3) 0.7114(3) 0.13078(14) 0.0473(7) Uani 1 1 d . . .
C4A C 0.2220(3) 0.8111(3) -0.00167(14) 0.0521(8) Uani 1 1 d . . .
C5A C 0.1558(3) 0.8919(3) 0.04199(15) 0.0528(8) Uani 1 1 d . . .
N1A N 0.7840(3) 0.6497(3) 0.26804(16) 0.0671(8) Uani 1 1 d . . .
O5A O 0.8616(3) 0.6913(3) 0.32112(14) 0.0934(8) Uani 1 1 d . . .
N2A N 0.7303(3) 1.0774(3) 0.26894(18) 0.0760(9) Uani 1 1 d . . .
C10A C 0.1774(3) 1.0188(3) 0.04389(16) 0.0606(8) Uani 1 1 d . . .
C6A C 0.0678(3) 0.8501(3) 0.08089(16) 0.0614(9) Uani 1 1 d . . .
H6A H 0.0539 0.7666 0.0820 0.074 Uiso 1 1 calc R . .
O2A O 0.4121(3) 1.0483(3) -0.05842(14) 0.0940(8) Uani 1 1 d . . .
C3A C 0.3046(3) 0.8622(3) -0.03750(16) 0.0615(9) Uani 1 1 d . . .
F1A F 0.2996(4) 0.4089(3) -0.0398(3) 0.1148(12) Uani 0.88 1 d P A 1
F2A F 0.1073(3) 0.4281(3) -0.0292(3) 0.1192(16) Uani 0.88 1 d P A 1
C22A C 0.4762(3) 0.9824(3) 0.18928(17) 0.0666(9) Uani 1 1 d . . .
H22D H 0.4266 0.9482 0.1445 0.100 Uiso 1 1 calc R . .
H22E H 0.5287 1.0629 0.1925 0.100 Uiso 1 1 calc R . .
H22F H 0.4177 0.9918 0.2215 0.100 Uiso 1 1 calc R . .
C23A C 0.2307(4) 0.4705(3) 0.0002(2) 0.0678(10) Uani 1 1 d . . .
O7A O 0.6891(3) 1.1317(3) 0.31726(16) 0.1182(11) Uani 1 1 d . . .
O6A O 0.8034(3) 1.1275(3) 0.23855(19) 0.1240(12) Uani 1 1 d . . .
C7A C 0.0017(3) 0.9314(4) 0.11751(18) 0.0740(10) Uani 1 1 d . . .
H7A H -0.0580 0.9023 0.1426 0.089 Uiso 1 1 calc R . .
C21A C 0.8948(3) 0.9273(4) 0.31124(19) 0.0830(11) Uani 1 1 d . . .
H21D H 0.8880 0.9238 0.3567 0.124 Uiso 1 1 calc R . .
H21E H 0.9178 1.0133 0.3103 0.124 Uiso 1 1 calc R . .
H21F H 0.9610 0.8833 0.2956 0.124 Uiso 1 1 calc R . .
C9A C 0.1118(4) 1.1012(3) 0.08042(17) 0.0724(10) Uani 1 1 d . . .
H9A H 0.1268 1.1853 0.0803 0.087 Uiso 1 1 calc R . .
C1A C 0.3695(4) 0.7861(4) -0.0834(2) 0.0756(11) Uani 1 1 d . . .
C2A C 0.3329(4) 0.9968(4) -0.03124(19) 0.0706(10) Uani 1 1 d . . .
N3A N 0.4178(4) 0.7238(4) -0.1209(2) 0.1057(12) Uani 1 1 d . . .
C8A C 0.0235(4) 1.0563(4) 0.11716(18) 0.0780(11) Uani 1 1 d . . .
H8A H -0.0220 1.1106 0.1420 0.094 Uiso 1 1 calc R . .
F3A F 0.2441(6) 0.4343(3) 0.0567(2) 0.1341(17) Uani 0.88 1 d P A 1
O1 O 0.1820(2) 0.7878(2) 0.27668(11) 0.0618(6) Uani 1 1 d . . .
O2 O 0.0062(2) 0.6917(2) 0.20075(12) 0.0742(7) Uani 1 1 d . . .
C5 C 0.3424(3) 0.6740(3) 0.31068(15) 0.0514(8) Uani 1 1 d . . .
O3 O -0.0432(3) 0.5091(2) 0.37696(13) 0.0751(7) Uani 1 1 d . . .
C4 C 0.2579(3) 0.5573(3) 0.27039(14) 0.0486(7) Uani 1 1 d . . .
C12 C 0.2473(3) 0.3434(3) 0.28802(15) 0.0535(8) Uani 1 1 d . B .
C15 C 0.0140(3) 0.3515(3) 0.42009(14) 0.0491(7) Uani 1 1 d . . .
C16 C -0.0079(3) 0.2608(3) 0.45539(14) 0.0535(8) Uani 1 1 d . . .
C20 C -0.0792(3) 0.4221(3) 0.40940(15) 0.0541(8) Uani 1 1 d . . .
O8 O 0.2409(2) 0.4252(2) 0.42706(12) 0.0846(8) Uani 1 1 d . . .
C3 C 0.1438(3) 0.5630(3) 0.23345(15) 0.0522(8) Uani 1 1 d . . .
N1 N -0.2985(3) 0.4670(3) 0.41527(15) 0.0708(8) Uani 1 1 d . . .
C10 C 0.3008(3) 0.7855(3) 0.31193(15) 0.0550(8) Uani 1 1 d . . .
C14 C 0.1379(3) 0.3757(3) 0.39171(16) 0.0538(8) Uani 1 1 d . . .
N2 N -0.1512(3) 0.1457(3) 0.51322(16) 0.0708(8) Uani 1 1 d . . .
C18 C -0.2270(3) 0.3068(3) 0.46622(14) 0.0540(8) Uani 1 1 d . . .
C17 C -0.1278(3) 0.2434(3) 0.47677(14) 0.0562(8) Uani 1 1 d . . .
F3 F 0.3367(4) 0.2108(3) 0.34426(17) 0.1038(11) Uani 0.88 1 d P B 1
C6 C 0.4646(3) 0.6810(3) 0.34808(16) 0.0601(8) Uani 1 1 d . . .
H6 H 0.4943 0.6076 0.3490 0.072 Uiso 1 1 calc R . .
C13 C 0.1227(3) 0.3322(3) 0.31575(15) 0.0590(8) Uani 1 1 d . . .
H13A H 0.0777 0.2450 0.3009 0.071 Uiso 1 1 calc R . .
H13B H 0.0676 0.3806 0.2965 0.071 Uiso 1 1 calc R . .
F2 F 0.2432(4) 0.1286(3) 0.2437(2) 0.1223(13) Uani 0.88 1 d P B 1
F1 F 0.4316(3) 0.2509(3) 0.2670(2) 0.1170(10) Uani 0.88 1 d P B 1
C19 C -0.2001(3) 0.3977(3) 0.43108(14) 0.0532(8) Uani 1 1 d . . .
C1 C 0.0594(3) 0.4530(4) 0.18896(17) 0.0620(9) Uani 1 1 d . . .
C11 C 0.3038(3) 0.4390(3) 0.26821(15) 0.0554(8) Uani 1 1 d . . .
H11 H 0.3807 0.4312 0.2511 0.066 Uiso 1 1 calc R . .
O4 O -0.2603(3) 0.5727(3) 0.40792(16) 0.1022(9) Uani 1 1 d . . .
N3 N -0.0076(3) 0.3657(3) 0.15370(16) 0.0884(10) Uani 1 1 d . . .
C9 C 0.3760(4) 0.9002(3) 0.34826(18) 0.0719(10) Uani 1 1 d . . .
H9 H 0.3456 0.9739 0.3492 0.086 Uiso 1 1 calc R . .
C2 C 0.1036(3) 0.6816(3) 0.23413(16) 0.0573(8) Uani 1 1 d . . .
O7 O -0.1073(3) 0.1729(3) 0.57254(15) 0.1215(12) Uani 1 1 d . . .
C7 C 0.5403(3) 0.7940(4) 0.38318(18) 0.0728(10) Uani 1 1 d . . .
H7 H 0.6218 0.7975 0.4074 0.087 Uiso 1 1 calc R . .
O6 O -0.2116(3) 0.0427(3) 0.48215(15) 0.1067(10) Uani 1 1 d . . .
O5 O -0.4111(3) 0.4245(3) 0.41170(18) 0.1251(12) Uani 1 1 d . . .
C22 C -0.3533(3) 0.2787(4) 0.49235(19) 0.0792(11) Uani 1 1 d . . .
H22A H -0.4224 0.2368 0.4550 0.119 Uiso 1 1 calc R . .
H22B H -0.3738 0.3558 0.5167 0.119 Uiso 1 1 calc R . .
H22C H -0.3442 0.2255 0.5220 0.119 Uiso 1 1 calc R . .
C23 C 0.3138(5) 0.2341(4) 0.2835(3) 0.0799(11) Uani 1 1 d D . .
C21 C 0.0923(3) 0.1821(3) 0.46696(19) 0.0778(10) Uani 1 1 d . . .
H21A H 0.1539 0.1877 0.4367 0.117 Uiso 1 1 calc R . .
H21B H 0.0490 0.0961 0.4587 0.117 Uiso 1 1 calc R . .
H21C H 0.1373 0.2125 0.5128 0.117 Uiso 1 1 calc R . .
C8 C 0.4971(4) 0.9037(4) 0.3832(2) 0.0833(11) Uani 1 1 d . . .
H8 H 0.5501 0.9806 0.4069 0.100 Uiso 1 1 calc R . .
H3 H -0.101(3) 0.550(3) 0.3800(17) 0.077(12) Uiso 1 1 d . . .
F4 F 0.332(2) 0.418(2) 0.0126(16) 0.082(6) Uani 0.12 1 d PU A 2
F5 F 0.171(4) 0.418(2) -0.0613(12) 0.103(8) Uani 0.12 1 d PU A 2
F9 F 0.158(3) 0.439(2) 0.0359(14) 0.071(6) Uani 0.12 1 d PU A 2
H3A H 0.612(4) 0.528(4) 0.186(2) 0.128(18) Uiso 1 1 d . . .
F6 F 0.330(3) 0.201(2) 0.2190(8) 0.083(5) Uani 0.12 1 d PDU B 2
F7 F 0.212(3) 0.150(2) 0.295(2) 0.152(11) Uani 0.12 1 d PDU B 2
F8 F 0.408(3) 0.228(4) 0.3252(18) 0.156(15) Uani 0.12 1 d PDU B 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
O3A C20A 1.348(3) . ?
O3A H3A 0.89(5) . ?
O1A C10A 1.377(4) . ?
O1A C2A 1.354(4) . ?
C20A C15A 1.394(4) . ?
C20A C19A 1.401(4) . ?
C16A C15A 1.388(4) . ?
C16A C17A 1.393(4) . ?
C16A C22A 1.496(4) . ?
O8A C14A 1.206(3) . ?
O4A N1A 1.215(3) . ?
C15A C14A 1.497(4) . ?
C18A C19A 1.400(4) . ?
C18A C17A 1.371(4) . ?
C18A C21A 1.508(4) . ?
C19A N1A 1.456(4) . ?
C17A N2A 1.482(4) . ?
C12A C13A 1.497(4) . ?
C12A C11A 1.316(4) . ?
C12A C23A 1.496(4) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.503(4) . ?
C11A H11A 0.9300 . ?
C11A C4A 1.485(4) . ?
C4A C5A 1.443(4) . ?
C4A C3A 1.353(4) . ?
C5A C10A 1.392(4) . ?
C5A C6A 1.394(4) . ?
N1A O5A 1.224(3) . ?
N2A O7A 1.205(4) . ?
N2A O6A 1.203(4) . ?
C10A C9A 1.377(5) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.374(5) . ?
O2A C2A 1.206(4) . ?
C3A C1A 1.431(5) . ?
C3A C2A 1.460(5) . ?
F1A C23A 1.311(5) . ?
F2A C23A 1.322(5) . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23A F3A 1.325(5) . ?
C23A F4 1.33(2) . ?
C23A F5 1.30(2) . ?
C23A F9 1.197(18) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.383(5) . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C9A H9A 0.9300 . ?
C9A C8A 1.378(5) . ?
C1A N3A 1.139(4) . ?
C8A H8A 0.9300 . ?
O1 C10 1.377(4) . ?
O1 C2 1.365(4) . ?
O2 C2 1.203(4) . ?
C5 C4 1.450(4) . ?
C5 C10 1.386(4) . ?
C5 C6 1.399(4) . ?
O3 C20 1.342(4) . ?
O3 H3 0.82(3) . ?
C4 C3 1.363(4) . ?
C4 C11 1.477(4) . ?
C12 C13 1.492(4) . ?
C12 C11 1.316(4) . ?
C12 C23 1.497(5) . ?
C15 C16 1.395(4) . ?
C15 C20 1.387(4) . ?
C15 C14 1.504(4) . ?
C16 C17 1.386(4) . ?
C16 C21 1.515(4) . ?
C20 C19 1.406(4) . ?
O8 C14 1.197(3) . ?
C3 C1 1.430(5) . ?
C3 C2 1.457(4) . ?
N1 C19 1.445(4) . ?
N1 O4 1.239(4) . ?
N1 O5 1.189(4) . ?
C10 C9 1.377(4) . ?
C14 C13 1.507(4) . ?
N2 C17 1.478(4) . ?
N2 O7 1.202(3) . ?
N2 O6 1.204(3) . ?
C18 C17 1.381(4) . ?
C18 C19 1.400(4) . ?
C18 C22 1.509(4) . ?
F3 C23 1.347(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.359(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
F2 C23 1.311(5) . ?
F1 C23 1.321(5) . ?
C1 N3 1.135(4) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.376(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 F6 1.333(14) . ?
C23 F7 1.383(18) . ?
C23 F8 1.256(19) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C8 H8 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
C20A O3A H3A 101(3) . . ?
C2A O1A C10A 122.1(3) . . ?
O3A C20A C15A 114.7(3) . . ?
O3A C20A C19A 126.1(3) . . ?
C15A C20A C19A 119.0(3) . . ?
C15A C16A C17A 116.6(3) . . ?
C15A C16A C22A 121.2(3) . . ?
C17A C16A C22A 122.2(3) . . ?
C20A C15A C14A 119.0(3) . . ?
C16A C15A C20A 120.8(3) . . ?
C16A C15A C14A 120.2(3) . . ?
C19A C18A C21A 124.8(3) . . ?
C17A C18A C19A 115.0(3) . . ?
C17A C18A C21A 120.2(3) . . ?
C20A C19A N1A 117.2(3) . . ?
C18A C19A C20A 122.2(3) . . ?
C18A C19A N1A 120.6(3) . . ?
C16A C17A N2A 116.6(3) . . ?
C18A C17A C16A 126.0(3) . . ?
C18A C17A N2A 117.4(3) . . ?
C11A C12A C13A 125.2(3) . . ?
C11A C12A C23A 119.0(3) . . ?
C23A C12A C13A 115.7(3) . . ?
C12A C13A H13C 109.0 . . ?
C12A C13A H13D 109.0 . . ?
C12A C13A C14A 113.1(2) . . ?
H13C C13A H13D 107.8 . . ?
C14A C13A H13C 109.0 . . ?
C14A C13A H13D 109.0 . . ?
C12A C11A H11A 117.3 . . ?
C12A C11A C4A 125.5(3) . . ?
C4A C11A H11A 117.3 . . ?
O8A C14A C15A 121.3(2) . . ?
O8A C14A C13A 122.0(3) . . ?
C15A C14A C13A 116.6(2) . . ?
C5A C4A C11A 120.1(3) . . ?
C3A C4A C11A 121.1(3) . . ?
C3A C4A C5A 118.7(3) . . ?
C10A C5A C4A 118.3(3) . . ?
C10A C5A C6A 117.7(3) . . ?
C6A C5A C4A 124.0(3) . . ?
O4A N1A C19A 119.7(3) . . ?
O4A N1A O5A 122.4(3) . . ?
O5A N1A C19A 117.9(3) . . ?
O7A N2A C17A 117.2(3) . . ?
O6A N2A C17A 118.1(3) . . ?
O6A N2A O7A 124.7(4) . . ?
O1A C10A C5A 121.5(3) . . ?
C9A C10A O1A 116.2(3) . . ?
C9A C10A C5A 122.3(3) . . ?
C5A C6A H6A 119.7 . . ?
C7A C6A C5A 120.5(3) . . ?
C7A C6A H6A 119.7 . . ?
C4A C3A C1A 121.3(3) . . ?
C4A C3A C2A 122.2(3) . . ?
C1A C3A C2A 116.6(3) . . ?
C16A C22A H22D 109.5 . . ?
C16A C22A H22E 109.5 . . ?
C16A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
F1A C23A C12A 111.7(3) . . ?
F1A C23A F2A 105.9(4) . . ?
F1A C23A F3A 106.6(5) . . ?
F1A C23A F4 47.9(13) . . ?
F2A C23A C12A 113.5(3) . . ?
F2A C23A F3A 106.9(4) . . ?
F2A C23A F4 135.0(10) . . ?
F3A C23A C12A 111.8(3) . . ?
F3A C23A F4 62.6(13) . . ?
F4 C23A C12A 110.6(9) . . ?
F5 C23A C12A 112.4(11) . . ?
F5 C23A F1A 65.0(17) . . ?
F5 C23A F2A 44.7(16) . . ?
F5 C23A F3A 134.8(11) . . ?
F5 C23A F4 109.4(18) . . ?
F9 C23A C12A 114.5(11) . . ?
F9 C23A F1A 132.5(12) . . ?
F9 C23A F2A 64.7(14) . . ?
F9 C23A F3A 45.1(15) . . ?
F9 C23A F4 103.9(17) . . ?
F9 C23A F5 105.7(17) . . ?
C6A C7A H7A 119.9 . . ?
C6A C7A C8A 120.2(3) . . ?
C8A C7A H7A 119.9 . . ?
C18A C21A H21D 109.5 . . ?
C18A C21A H21E 109.5 . . ?
C18A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C10A C9A H9A 120.8 . . ?
C10A C9A C8A 118.4(4) . . ?
C8A C9A H9A 120.8 . . ?
N3A C1A C3A 178.0(5) . . ?
O1A C2A C3A 117.0(3) . . ?
O2A C2A O1A 118.1(3) . . ?
O2A C2A C3A 124.9(4) . . ?
C7A C8A H8A 119.6 . . ?
C9A C8A C7A 120.7(4) . . ?
C9A C8A H8A 119.6 . . ?
C2 O1 C10 121.8(3) . . ?
C10 C5 C4 118.5(3) . . ?
C10 C5 C6 117.7(3) . . ?
C6 C5 C4 123.8(3) . . ?
C20 O3 H3 103(3) . . ?
C5 C4 C11 118.2(3) . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C11 123.3(3) . . ?
C13 C12 C23 115.6(3) . . ?
C11 C12 C13 126.7(3) . . ?
C11 C12 C23 117.7(3) . . ?
C16 C15 C14 121.7(3) . . ?
C20 C15 C16 120.7(3) . . ?
C20 C15 C14 117.6(3) . . ?
C15 C16 C21 121.4(3) . . ?
C17 C16 C15 116.5(3) . . ?
C17 C16 C21 122.0(3) . . ?
O3 C20 C15 114.4(3) . . ?
O3 C20 C19 125.8(3) . . ?
C15 C20 C19 119.9(3) . . ?
C4 C3 C1 121.8(3) . . ?
C4 C3 C2 122.2(3) . . ?
C1 C3 C2 115.9(3) . . ?
O4 N1 C19 117.4(3) . . ?
O5 N1 C19 120.5(4) . . ?
O5 N1 O4 122.1(3) . . ?
O1 C10 C5 121.8(3) . . ?
O1 C10 C9 116.2(3) . . ?
C9 C10 C5 122.0(3) . . ?
C15 C14 C13 115.1(3) . . ?
O8 C14 C15 122.3(3) . . ?
O8 C14 C13 122.6(3) . . ?
O7 N2 C17 118.1(3) . . ?
O7 N2 O6 123.2(3) . . ?
O6 N2 C17 118.7(3) . . ?
C17 C18 C19 115.2(3) . . ?
C17 C18 C22 120.9(3) . . ?
C19 C18 C22 123.9(3) . . ?
C16 C17 N2 116.2(3) . . ?
C18 C17 C16 126.2(3) . . ?
C18 C17 N2 117.5(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C12 C13 C14 115.2(3) . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C20 C19 N1 118.6(3) . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 N1 120.0(3) . . ?
N3 C1 C3 179.9(5) . . ?
C4 C11 H11 116.6 . . ?
C12 C11 C4 126.8(3) . . ?
C12 C11 H11 116.6 . . ?
C10 C9 H9 120.7 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 H9 120.7 . . ?
O1 C2 C3 117.0(3) . . ?
O2 C2 O1 118.3(3) . . ?
O2 C2 C3 124.6(3) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.5(4) . . ?
C8 C7 H7 119.8 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F3 C23 C12 110.8(4) . . ?
F3 C23 F7 67.1(18) . . ?
F2 C23 C12 113.4(4) . . ?
F2 C23 F3 104.5(4) . . ?
F2 C23 F1 109.1(4) . . ?
F2 C23 F6 61.4(11) . . ?
F2 C23 F7 49.1(16) . . ?
F1 C23 C12 115.2(4) . . ?
F1 C23 F3 102.7(4) . . ?
F1 C23 F6 59.2(12) . . ?
F1 C23 F7 146.5(12) . . ?
F6 C23 C12 104.1(8) . . ?
F6 C23 F3 145.1(8) . . ?
F6 C23 F7 110.2(19) . . ?
F7 C23 C12 97.9(12) . . ?
F8 C23 C12 125.9(18) . . ?
F8 C23 F3 40.3(19) . . ?
F8 C23 F2 117.8(19) . . ?
F8 C23 F1 62(2) . . ?
F8 C23 F6 115(2) . . ?
F8 C23 F7 102(2) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?

