# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_2Acr-op863
_database_code_depnum_ccdc_archive 'CCDC 1580786'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-aminoheptafluoronaphthalene 18-crown-6 2:1 associate
;
_chemical_name_common            ?
_chemical_melting_point          368
_chemical_formula_moiety         '2(C10 H2 F7 N),  C12 H24 O6'
_chemical_formula_sum            'C32 H28 F14 N2 O6'
_chemical_formula_weight         802.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.5564(4)
_cell_length_b                   12.4605(5)
_cell_length_c                   17.0460(7)
_cell_angle_alpha                79.561(2)
_cell_angle_beta                 85.274(2)
_cell_angle_gamma                71.155(2)
_cell_volume                     1690.95(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51148
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         27.28
_reflns_number_total             7523
_reflns_number_gt                5399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0901P)²+0.2389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7523
_refine_ls_number_parameters     503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36290(18) 0.38426(13) 0.32210(9) 0.0330(3) Uani 1 1 d . . .
F1 F 0.27400(12) 0.40878(9) 0.38958(5) 0.0503(3) Uani 1 1 d . . .
N1 N 0.13833(19) 0.52351(13) 0.24702(10) 0.0441(3) Uani 1 1 d . . .
H1 H 0.093(3) 0.5464(17) 0.2860(13) 0.047(5) Uiso 1 1 d . . .
H2 H 0.097(3) 0.559(2) 0.2005(16) 0.074(7) Uiso 1 1 d . . .
C2 C 0.28907(19) 0.44422(12) 0.25128(9) 0.0338(3) Uani 1 1 d . . .
F2 F 0.31730(16) 0.46816(10) 0.11112(6) 0.0616(3) Uani 1 1 d . . .
C3 C 0.3823(2) 0.41358(14) 0.18215(9) 0.0403(4) Uani 1 1 d . . .
F3 F 0.60927(17) 0.30855(11) 0.11437(7) 0.0718(4) Uani 1 1 d . . .
C4A C 0.60659(19) 0.26932(13) 0.25638(10) 0.0369(3) Uani 1 1 d . . .
C4 C 0.5318(2) 0.33111(14) 0.18416(10) 0.0431(4) Uani 1 1 d . . .
F4 F 0.84689(14) 0.15177(10) 0.19570(8) 0.0670(3) Uani 1 1 d . . .
C5 C 0.7595(2) 0.18051(15) 0.26217(12) 0.0459(4) Uani 1 1 d . . .
F5 F 0.96683(13) 0.03672(9) 0.33791(9) 0.0697(4) Uani 1 1 d . . .
C6 C 0.8219(2) 0.12210(14) 0.33330(13) 0.0488(4) Uani 1 1 d . . .
F6 F 0.80202(14) 0.09319(10) 0.47413(8) 0.0688(3) Uani 1 1 d . . .
C7 C 0.7367(2) 0.15063(15) 0.40415(12) 0.0476(4) Uani 1 1 d . . .
F7 F 0.51282(14) 0.26133(10) 0.47111(6) 0.0608(3) Uani 1 1 d . . .
C8A C 0.51734(18) 0.29805(12) 0.32824(9) 0.0333(3) Uani 1 1 d . . .
C8 C 0.5895(2) 0.23621(14) 0.40137(10) 0.0415(4) Uani 1 1 d . . .
N2 N 0.89813(19) -0.16388(14) 0.20703(11) 0.0465(4) Uani 1 1 d . . .
H3 H 0.940(3) -0.1994(19) 0.2499(14) 0.062(6) Uiso 1 1 d . . .
H4 H 0.939(3) -0.1861(18) 0.1622(14) 0.061(6) Uiso 1 1 d . . .
F8 F 0.73477(12) -0.12191(8) 0.34715(5) 0.0453(2) Uani 1 1 d . . .
C9 C 0.65709(18) -0.06436(12) 0.27894(8) 0.0307(3) Uani 1 1 d . . .
F9 F 0.74284(14) -0.04311(10) 0.06851(6) 0.0613(3) Uani 1 1 d . . .
C10 C 0.74409(18) -0.08871(12) 0.20921(9) 0.0336(3) Uani 1 1 d . . .
F10 F 0.44753(15) 0.11341(10) 0.06835(6) 0.0649(3) Uani 1 1 d . . .
C11 C 0.6629(2) -0.02460(14) 0.13866(9) 0.0393(4) Uani 1 1 d . . .
F11 F 0.19480(13) 0.22986(10) 0.14832(7) 0.0631(3) Uani 1 1 d . . .
C12A C 0.42411(18) 0.08110(12) 0.21049(9) 0.0331(3) Uani 1 1 d . . .
C12 C 0.5118(2) 0.05584(14) 0.13925(9) 0.0402(4) Uani 1 1 d . . .
F12 F 0.04697(12) 0.26984(9) 0.28935(8) 0.0646(3) Uani 1 1 d . . .
C13 C 0.2688(2) 0.16582(13) 0.21523(11) 0.0407(4) Uani 1 1 d . . .
F13 F 0.18510(16) 0.14539(11) 0.42596(7) 0.0704(3) Uani 1 1 d . . .
C14 C 0.1931(2) 0.18686(13) 0.28579(12) 0.0448(4) Uani 1 1 d . . .
F14 F 0.47939(14) -0.01960(10) 0.42518(6) 0.0574(3) Uani 1 1 d . . .
C15 C 0.2652(2) 0.12291(14) 0.35691(11) 0.0443(4) Uani 1 1 d . . .
C16 C 0.4143(2) 0.03984(13) 0.35614(9) 0.0375(3) Uani 1 1 d . . .
C16A C 0.50083(17) 0.01670(11) 0.28336(8) 0.0290(3) Uani 1 1 d . . .
O1 O 1.15509(13) 0.74485(9) 0.34695(6) 0.0407(3) Uani 1 1 d . . .
O2 O 1.28193(14) 0.76434(9) 0.18171(6) 0.0410(3) Uani 1 1 d . . .
O3 O 1.08173(14) 0.74649(11) 0.06463(6) 0.0450(3) Uani 1 1 d . . .
O4 O 0.87799(14) 0.60741(10) 0.10897(6) 0.0453(3) Uani 1 1 d . . .
O5 O 0.74773(14) 0.59578(9) 0.27350(7) 0.0407(3) Uani 1 1 d . . .
O6 O 0.94853(13) 0.60836(9) 0.39423(6) 0.0398(3) Uani 1 1 d . . .
C17 C 1.3147(2) 0.75014(17) 0.32088(11) 0.0507(4) Uani 1 1 d . . .
H17A H 1.3903 0.6717 0.3180 0.061 Uiso 1 1 calc R . .
H17B H 1.3589 0.7826 0.3597 0.061 Uiso 1 1 calc R . .
C18 C 1.3068(2) 0.82307(16) 0.24092(11) 0.0493(4) Uani 1 1 d . . .
H18A H 1.2150 0.8959 0.2407 0.059 Uiso 1 1 calc R . .
H18B H 1.4111 0.8419 0.2290 0.059 Uiso 1 1 calc R . .
C19 C 1.2635(2) 0.83318(15) 0.10546(10) 0.0462(4) Uani 1 1 d . . .
H19A H 1.3641 0.8556 0.0901 0.055 Uiso 1 1 calc R . .
H19B H 1.1685 0.9041 0.1065 0.055 Uiso 1 1 calc R . .
C20 C 1.2354(2) 0.76694(16) 0.04616(10) 0.0467(4) Uani 1 1 d . . .
H20A H 1.2344 0.8111 -0.0084 0.056 Uiso 1 1 calc R . .
H20B H 1.3257 0.6929 0.0482 0.056 Uiso 1 1 calc R . .
C21 C 1.0439(2) 0.68457(16) 0.01033(9) 0.0482(4) Uani 1 1 d . . .
H21A H 1.1273 0.6074 0.0135 0.058 Uiso 1 1 calc R . .
H21B H 1.0456 0.7260 -0.0449 0.058 Uiso 1 1 calc R . .
C22 C 0.8768(2) 0.67336(17) 0.03164(10) 0.0510(4) Uani 1 1 d . . .
H22A H 0.7946 0.7506 0.0306 0.061 Uiso 1 1 calc R . .
H22B H 0.8451 0.6354 -0.0079 0.061 Uiso 1 1 calc R . .
C23 C 0.7170(2) 0.60479(18) 0.13489(11) 0.0517(4) Uani 1 1 d . . .
H23A H 0.6724 0.5714 0.0968 0.062 Uiso 1 1 calc R . .
H23B H 0.6429 0.6841 0.1362 0.062 Uiso 1 1 calc R . .
C24 C 0.7221(2) 0.53472(16) 0.21589(11) 0.0489(4) Uani 1 1 d . . .
H24A H 0.6167 0.5175 0.2281 0.059 Uiso 1 1 calc R . .
H24B H 0.8126 0.4610 0.2175 0.059 Uiso 1 1 calc R . .
C25 C 0.7567(2) 0.53193(14) 0.35113(10) 0.0426(4) Uani 1 1 d . . .
H25A H 0.8477 0.4584 0.3533 0.051 Uiso 1 1 calc R . .
H25B H 0.6521 0.5144 0.3657 0.051 Uiso 1 1 calc R . .
C26 C 0.78639(19) 0.60047(14) 0.40840(9) 0.0414(4) Uani 1 1 d . . .
H26A H 0.7044 0.6783 0.4009 0.050 Uiso 1 1 calc R . .
H26B H 0.7747 0.5627 0.4639 0.050 Uiso 1 1 calc R . .
C27 C 0.9893(2) 0.67076(14) 0.44715(9) 0.0418(4) Uani 1 1 d . . .
H27A H 0.9880 0.6305 0.5028 0.050 Uiso 1 1 calc R . .
H27B H 0.9072 0.7484 0.4436 0.050 Uiso 1 1 calc R . .
C28 C 1.1569(2) 0.68010(14) 0.42462(9) 0.0442(4) Uani 1 1 d . . .
H28A H 1.1908 0.7181 0.4634 0.053 Uiso 1 1 calc R . .
H28B H 1.2378 0.6024 0.4258 0.053 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.3520(17) . ?
C1 C2 1.382(2) . ?
C1 C8A 1.406(2) . ?
N1 C2 1.346(2) . ?
C2 C3 1.408(2) . ?
F2 C3 1.3438(19) . ?
C3 C4 1.356(3) . ?
F3 C4 1.3433(18) . ?
C4A C4 1.409(2) . ?
C4A C5 1.412(2) . ?
C4A C8A 1.428(2) . ?
F4 C5 1.344(2) . ?
C5 C6 1.349(3) . ?
F5 C6 1.345(2) . ?
C6 C7 1.400(3) . ?
F6 C7 1.338(2) . ?
C7 C8 1.360(2) . ?
F7 C8 1.3474(19) . ?
C8A C8 1.414(2) . ?
N2 C10 1.350(2) . ?
F8 C9 1.3511(16) . ?
C9 C10 1.378(2) . ?
C9 C16A 1.397(2) . ?
F9 C11 1.3470(18) . ?
C10 C11 1.413(2) . ?
F10 C12 1.3485(17) . ?
C11 C12 1.356(2) . ?
F11 C13 1.3423(19) . ?
C12A C12 1.405(2) . ?
C12A C13 1.412(2) . ?
C12A C16A 1.4320(19) . ?
F12 C14 1.3459(19) . ?
C13 C14 1.346(3) . ?
F13 C15 1.340(2) . ?
C14 C15 1.393(3) . ?
F14 C16 1.3303(18) . ?
C15 C16 1.360(2) . ?
C16 C16A 1.418(2) . ?
O1 C17 1.420(2) . ?
O1 C28 1.4186(19) . ?
O2 C19 1.412(2) . ?
O2 C18 1.415(2) . ?
O3 C20 1.419(2) . ?
O3 C21 1.423(2) . ?
O4 C23 1.420(2) . ?
O4 C22 1.420(2) . ?
O5 C25 1.4092(19) . ?
O5 C24 1.416(2) . ?
O6 C26 1.4202(19) . ?
O6 C27 1.4216(19) . ?
C17 C18 1.488(3) . ?
C19 C20 1.493(3) . ?
C21 C22 1.490(3) . ?
C23 C24 1.490(3) . ?
C25 C26 1.494(2) . ?
C27 C28 1.490(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 116.07(13) . . ?
F1 C1 C8A 118.89(13) . . ?
C2 C1 C8A 124.98(14) . . ?
N1 C2 C1 123.79(14) . . ?
N1 C2 C3 121.57(15) . . ?
C1 C2 C3 114.61(14) . . ?
F2 C3 C4 119.08(14) . . ?
F2 C3 C2 117.73(15) . . ?
C4 C3 C2 123.18(15) . . ?
C4 C4A C5 124.75(15) . . ?
C4 C4A C8A 116.69(14) . . ?
C5 C4A C8A 118.55(16) . . ?
F3 C4 C3 118.02(16) . . ?
F3 C4 C4A 119.76(15) . . ?
C3 C4 C4A 122.22(14) . . ?
F4 C5 C6 118.17(16) . . ?
F4 C5 C4A 120.02(17) . . ?
C6 C5 C4A 121.81(16) . . ?
F5 C6 C5 121.19(18) . . ?
F5 C6 C7 118.68(18) . . ?
C5 C6 C7 120.13(15) . . ?
F6 C7 C8 120.72(17) . . ?
F6 C7 C6 119.26(16) . . ?
C8 C7 C6 120.01(17) . . ?
C1 C8A C8 124.11(14) . . ?
C1 C8A C4A 118.32(14) . . ?
C8 C8A C4A 117.56(14) . . ?
F7 C8 C7 117.88(15) . . ?
F7 C8 C8A 120.21(14) . . ?
C7 C8 C8A 121.91(16) . . ?
F8 C9 C10 115.82(13) . . ?
F8 C9 C16A 119.16(13) . . ?
C10 C9 C16A 124.98(13) . . ?
N2 C10 C9 123.54(14) . . ?
N2 C10 C11 121.55(15) . . ?
C9 C10 C11 114.85(13) . . ?
F9 C11 C12 119.48(14) . . ?
F9 C11 C10 117.70(14) . . ?
C12 C11 C10 122.80(14) . . ?
C12 C12A C13 124.94(14) . . ?
C12 C12A C16A 116.82(13) . . ?
C13 C12A C16A 118.23(14) . . ?
F10 C12 C11 117.71(15) . . ?
F10 C12 C12A 120.11(14) . . ?
C11 C12 C12A 122.18(13) . . ?
F11 C13 C14 118.26(15) . . ?
F11 C13 C12A 120.00(16) . . ?
C14 C13 C12A 121.73(15) . . ?
C13 C14 F12 121.00(16) . . ?
C13 C14 C15 120.42(15) . . ?
F12 C14 C15 118.59(17) . . ?
F13 C15 C16 120.76(16) . . ?
F13 C15 C14 118.70(16) . . ?
C16 C15 C14 120.54(15) . . ?
F14 C16 C15 118.93(15) . . ?
F14 C16 C16A 119.99(14) . . ?
C15 C16 C16A 121.08(14) . . ?
C9 C16A C16 123.67(13) . . ?
C9 C16A C12A 118.36(13) . . ?
C16 C16A C12A 117.97(13) . . ?
C17 O1 C28 111.77(13) . . ?
C19 O2 C18 111.98(13) . . ?
C20 O3 C21 112.59(12) . . ?
C23 O4 C22 111.47(13) . . ?
C25 O5 C24 111.90(12) . . ?
C26 O6 C27 112.72(12) . . ?
O1 C17 C18 110.28(14) . . ?
O2 C18 C17 110.07(14) . . ?
O2 C19 C20 109.27(13) . . ?
O3 C20 C19 108.74(13) . . ?
O3 C21 C22 108.61(14) . . ?
O4 C22 C21 109.77(13) . . ?
O4 C23 C24 110.28(14) . . ?
O5 C24 C23 109.76(14) . . ?
O5 C25 C26 109.01(12) . . ?
O6 C26 C25 108.65(12) . . ?
O6 C27 C28 108.68(12) . . ?
O1 C28 C27 109.72(12) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.28
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_2Bcr-m888
_database_code_depnum_ccdc_archive 'CCDC 1580787'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 pentafluoroaniline 18-crown-6 2:1 associate
;
_chemical_name_common            ?
_chemical_melting_point          353
_chemical_formula_moiety         '2(C6 H2 F5 N), C12 H24 O6'
_chemical_formula_sum            'C24 H28 F10 N2 O6'
_chemical_formula_weight         630.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.2488(4)
_cell_length_b                   9.8098(5)
_cell_length_c                   9.8855(5)
_cell_angle_alpha                105.139(3)
_cell_angle_beta                 105.804(3)
_cell_angle_gamma                114.814(2)
_cell_volume                     707.24(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4944
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8767
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13637
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3252
_reflns_number_gt                2252
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1033P)²+0.3221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2120(3) 0.1785(2) 0.3431(2) 0.0825(6) Uani 1 1 d . . .
O3 O 0.4480(3) 0.7661(3) 0.5114(3) 0.0892(7) Uani 1 1 d . . .
O2 O 0.1480(3) 0.4342(3) 0.4135(2) 0.0827(6) Uani 1 1 d . . .
C1 C 0.4792(3) 0.5665(3) 0.8157(2) 0.0539(5) Uani 1 1 d . . .
C2 C 0.3253(3) 0.4477(3) 0.8101(2) 0.0582(6) Uani 1 1 d . . .
C6 C 0.5563(3) 0.7258(3) 0.9285(2) 0.0584(6) Uani 1 1 d . . .
C4 C 0.3285(3) 0.6456(4) 1.0120(3) 0.0686(6) Uani 1 1 d . . .
C3 C 0.2505(3) 0.4859(3) 0.9051(3) 0.0636(6) Uani 1 1 d . . .
C5 C 0.4823(3) 0.7652(3) 1.0230(3) 0.0655(6) Uani 1 1 d . . .
C8 C 0.0445(4) 0.1482(4) 0.3237(4) 0.0949(11) Uani 1 1 d . . .
H8A H 0.0323 0.1531 0.4190 0.114 Uiso 1 1 calc R . .
H8B H -0.0461 0.0384 0.2409 0.114 Uiso 1 1 calc R . .
C7 C 0.2434(5) 0.0559(3) 0.3718(4) 0.0990(11) Uani 1 1 d . . .
H7A H 0.1461 -0.0542 0.2943 0.119 Uiso 1 1 calc R . .
H7B H 0.2509 0.0635 0.4735 0.119 Uiso 1 1 calc R . .
C9 C 0.0241(4) 0.2753(6) 0.2845(3) 0.0989(12) Uani 1 1 d . . .
H9A H 0.0449 0.2756 0.1936 0.119 Uiso 1 1 calc R . .
H9B H -0.0955 0.2507 0.2606 0.119 Uiso 1 1 calc R . .
C10 C 0.1389(5) 0.5640(6) 0.3881(5) 0.1052(13) Uani 1 1 d . . .
H10A H 0.0265 0.5517 0.3789 0.126 Uiso 1 1 calc R . .
H10B H 0.1470 0.5613 0.2918 0.126 Uiso 1 1 calc R . .
C11 C 0.2854(6) 0.7243(6) 0.5191(6) 0.1076(14) Uani 1 1 d . . .
H11A H 0.2613 0.8110 0.5163 0.129 Uiso 1 1 calc R . .
H11B H 0.2935 0.7172 0.6166 0.129 Uiso 1 1 calc R . .
C12 C 0.5907(6) 0.9174(4) 0.6347(4) 0.1000(11) Uani 1 1 d . . .
H12A H 0.5943 0.9156 0.7331 0.120 Uiso 1 1 calc R . .
H12B H 0.5760 1.0079 0.6273 0.120 Uiso 1 1 calc R . .
F1 F 0.2465(3) 0.28856(19) 0.70810(18) 0.0910(6) Uani 1 1 d . . .
F5 F 0.7110(2) 0.8468(2) 0.94699(18) 0.0913(6) Uani 1 1 d . . .
F4 F 0.5646(3) 0.9233(2) 1.1289(2) 0.1062(7) Uani 1 1 d . . .
F2 F 0.1015(2) 0.3659(2) 0.8943(2) 0.1021(6) Uani 1 1 d . . .
N1 N 0.5574(4) 0.5288(4) 0.7247(3) 0.0777(7) Uani 1 1 d . . .
H1A H 0.633(5) 0.609(4) 0.709(4) 0.087(10) Uiso 1 1 d . . .
H1B H 0.502(4) 0.434(4) 0.653(4) 0.088(10) Uiso 1 1 d . . .
F3 F 0.2543(3) 0.6847(3) 1.1026(3) 0.1109(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.396(4) . ?
O1 C7 1.428(4) . ?
O3 C12 1.402(4) . ?
O3 C11 1.413(4) . ?
O2 C10 1.391(4) . ?
O2 C9 1.427(4) . ?
C1 N1 1.369(3) . ?
C1 C6 1.384(3) . ?
C1 C2 1.385(3) . ?
C2 F1 1.345(3) . ?
C2 C3 1.374(3) . ?
C6 F5 1.345(3) . ?
C6 C5 1.369(3) . ?
C4 F3 1.341(3) . ?
C4 C5 1.364(4) . ?
C4 C3 1.365(4) . ?
C3 F2 1.337(3) . ?
C5 F4 1.344(3) . ?
C8 C9 1.466(5) . ?
C7 C12 1.467(5) 2_666 ?
C10 C11 1.475(6) . ?
C12 C7 1.467(5) 2_666 ?

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
C8 O1 C7 113.5(3) . . ?
C12 O3 C11 112.7(3) . . ?
C10 O2 C9 113.7(3) . . ?
N1 C1 C6 121.8(2) . . ?
N1 C1 C2 123.0(2) . . ?
C6 C1 C2 115.00(19) . . ?
F1 C2 C3 118.7(2) . . ?
F1 C2 C1 118.6(2) . . ?
C3 C2 C1 122.7(2) . . ?
F5 C6 C5 118.5(2) . . ?
F5 C6 C1 118.79(19) . . ?
C5 C6 C1 122.7(2) . . ?
F3 C4 C5 120.6(2) . . ?
F3 C4 C3 120.8(2) . . ?
C5 C4 C3 118.6(2) . . ?
F2 C3 C4 119.7(2) . . ?
F2 C3 C2 120.0(2) . . ?
C4 C3 C2 120.4(2) . . ?
F4 C5 C4 120.2(2) . . ?
F4 C5 C6 119.2(2) . . ?
C4 C5 C6 120.6(2) . . ?
O1 C8 C9 108.3(2) . . ?
O1 C7 C12 109.6(3) . 2_666 ?
O2 C9 C8 109.2(2) . . ?
O2 C10 C11 109.6(3) . . ?
O3 C11 C10 111.0(3) . . ?
O3 C12 C7 109.6(2) . 2_666 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_F-m22k
_database_code_depnum_ccdc_archive 'CCDC 1580791'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-aminotetrafluoropyridine  
;
_chemical_name_common            ?
_chemical_melting_point          358
_chemical_formula_moiety         'C5 H2 F4 N2'
_chemical_formula_sum            'C5 H2 F4 N2'
_chemical_formula_weight         166.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   6.1047(7)
_cell_length_b                   13.2859(11)
_cell_length_c                   7.4684(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.767(6)
_cell_angle_gamma                90.00
_cell_volume                     603.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4322
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      29.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9333
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         29.10
_reflns_number_total             1612
_reflns_number_gt                1264
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1258P)²+0.0348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4479(2) 0.76161(9) 0.23196(17) 0.0456(3) Uani 1 1 d . . .
N2 N 0.3005(3) 0.45988(10) 0.3143(2) 0.0595(4) Uani 1 1 d . . .
C3 C 0.3479(2) 0.55727(10) 0.28651(18) 0.0400(3) Uani 1 1 d . . .
C4 C 0.2126(2) 0.63586(10) 0.33541(18) 0.0410(3) Uani 1 1 d . . .
C5 C 0.2702(2) 0.73350(10) 0.30535(19) 0.0432(4) Uani 1 1 d . . .
C1 C 0.5771(2) 0.68838(11) 0.18539(19) 0.0438(4) Uani 1 1 d . . .
C2 C 0.5370(2) 0.58796(10) 0.20849(18) 0.0421(3) Uani 1 1 d . . .
F2 F 0.67667(17) 0.51745(8) 0.15810(16) 0.0637(3) Uani 1 1 d . . .
F3 F 0.02929(17) 0.61351(8) 0.41471(15) 0.0620(3) Uani 1 1 d . . .
F4 F 0.13849(18) 0.80703(8) 0.35542(16) 0.0659(4) Uani 1 1 d . . .
F1 F 0.75731(17) 0.71615(8) 0.10909(15) 0.0663(4) Uani 1 1 d . . .
H1 H 0.396(4) 0.414(2) 0.284(3) 0.079(7) Uiso 1 1 d . . .
H2 H 0.181(4) 0.4442(19) 0.366(3) 0.064(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.310(2) . ?
N1 C1 1.317(2) . ?
N2 C3 1.3458(18) . ?
C3 C2 1.3961(19) . ?
C3 C4 1.3986(19) . ?
C4 F3 1.3424(16) . ?
C4 C5 1.3674(19) . ?
C5 F4 1.3383(16) . ?
C1 F1 1.3324(17) . ?
C1 C2 1.370(2) . ?
C2 F2 1.3415(16) . ?

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
C5 N1 C1 115.77(12) . . ?
N2 C3 C2 122.76(13) . . ?
N2 C3 C4 122.56(14) . . ?
C2 C3 C4 114.68(12) . . ?
F3 C4 C5 121.16(13) . . ?
F3 C4 C3 118.83(12) . . ?
C5 C4 C3 119.99(13) . . ?
N1 C5 F4 116.52(13) . . ?
N1 C5 C4 124.92(13) . . ?
F4 C5 C4 118.55(14) . . ?
N1 C1 F1 116.24(13) . . ?
N1 C1 C2 124.66(14) . . ?
F1 C1 C2 119.09(14) . . ?
F2 C2 C1 121.35(13) . . ?
F2 C2 C3 118.68(12) . . ?
C1 C2 C3 119.97(13) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.10
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
#END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_2Dcr-mal8c
_database_code_depnum_ccdc_archive 'CCDC 1580789'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-cyano-2,3,5,6-tetrafluoroaniline 18-crown-6 2:1 associate
;
_chemical_name_common            ?
_chemical_melting_point          427
_chemical_formula_moiety         '2(C7 H2 F4 N2), C12 H24 O6'
_chemical_formula_sum            'C26 H28 F8 N4 O6'
_chemical_formula_weight         644.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c   '

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

_cell_length_a                   14.550(12)
_cell_length_b                   11.592(12)
_cell_length_c                   34.58(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.11(3)
_cell_angle_gamma                90.00
_cell_volume                     5832(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5411
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.83

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2656
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8510
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31201
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         25.19
_reflns_number_total             5233
_reflns_number_gt                3297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.,Highly disordered
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5233
_refine_ls_number_parameters     550
_refine_ls_number_restraints     386
_refine_ls_R_factor_all          0.1935
_refine_ls_R_factor_gt           0.1510
_refine_ls_wR_factor_ref         0.4817
_refine_ls_wR_factor_gt          0.4463
_refine_ls_goodness_of_fit_ref   1.903
_refine_ls_restrained_S_all      2.108
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

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
N1 N 0.4887(8) 0.561(2) 0.6671(10) 0.051(4) Uani 0.535(6) 1 d PU A 1
H1A H 0.4597 0.6217 0.6759 0.062 Uiso 0.535(6) 1 calc PR A 1
H1B H 0.5241 0.5662 0.6466 0.062 Uiso 0.535(6) 1 calc PR A 1
N2 N 0.3373(19) 0.094(3) 0.7414(6) 0.079(7) Uani 0.535(6) 1 d PU A 1
C1 C 0.4792(11) 0.4631(14) 0.6842(5) 0.046(4) Uani 0.535(6) 1 d PU A 1
C2 C 0.4186(7) 0.4765(9) 0.7164(3) 0.044(3) Uani 0.535(6) 1 d PU A 1
C3 C 0.3789(10) 0.3832(11) 0.7346(4) 0.044(3) Uani 0.535(6) 1 d PU A 1
C4 C 0.4024(7) 0.2699(10) 0.7237(3) 0.049(3) Uani 0.535(6) 1 d PU A 1
C5 C 0.4624(9) 0.2601(10) 0.6919(3) 0.052(3) Uani 0.535(6) 1 d PU A 1
C6 C 0.5000(4) 0.3493(5) 0.67339(17) 0.0450(14) Uani 0.535(6) 1 d PU A 1
C7 C 0.3648(15) 0.175(2) 0.7438(7) 0.049(5) Uani 0.535(6) 1 d PU A 1
F1 F 0.3993(5) 0.5820(6) 0.7284(2) 0.064(2) Uani 0.535(6) 1 d PU A 1
F2 F 0.3279(8) 0.3982(7) 0.7650(4) 0.068(3) Uani 0.535(6) 1 d PU A 1
F3 F 0.4821(12) 0.155(2) 0.6803(8) 0.076(5) Uani 0.535(6) 1 d PU A 1
F4 F 0.5560(5) 0.3333(6) 0.6436(2) 0.072(2) Uani 0.535(6) 1 d PU A 1
C1A C 0.5224(11) 0.4647(15) 0.6845(5) 0.038(4) Uani 0.465(6) 1 d PU A 2
C2A C 0.5804(7) 0.4756(9) 0.7161(3) 0.035(3) Uani 0.465(6) 1 d PU A 2
C3A C 0.6195(10) 0.3837(12) 0.7350(4) 0.037(3) Uani 0.465(6) 1 d PU A 2
C4A C 0.5977(7) 0.2690(10) 0.7233(3) 0.041(3) Uani 0.465(6) 1 d PU A 2
C5A C 0.5390(9) 0.2583(10) 0.6924(4) 0.043(3) Uani 0.465(6) 1 d PU A 2
C6A C 0.5000(4) 0.3493(5) 0.67339(17) 0.0450(14) Uani 0.465(6) 1 d PU A 2
C7A C 0.6327(19) 0.172(3) 0.7408(7) 0.056(7) Uani 0.465(6) 1 d PU A 2
F1A F 0.6005(5) 0.5820(6) 0.7290(2) 0.056(2) Uani 0.465(6) 1 d PU A 2
F2A F 0.6735(8) 0.3996(8) 0.7655(4) 0.058(3) Uani 0.465(6) 1 d PU A 2
F3A F 0.5166(13) 0.148(2) 0.6789(8) 0.062(5) Uani 0.465(6) 1 d PU A 2
F4A F 0.4433(6) 0.3337(6) 0.6437(2) 0.065(3) Uani 0.465(6) 1 d PU A 2
N1A N 0.5165(12) 0.550(2) 0.6660(11) 0.04683(1) Uani 0.465(6) 1 d PU A 2
H1A1 H 0.4961 0.5463 0.6421 0.056 Uiso 0.465(6) 1 calc PR A 2
H1A2 H 0.5326 0.6162 0.6762 0.056 Uiso 0.465(6) 1 calc PR A 2
N2A N 0.664(2) 0.093(3) 0.7416(7) 0.067(6) Uani 0.465(6) 1 d PU A 2
O1 O 0.6605(6) 0.5368(8) 0.6023(3) 0.130(3) Uani 1 1 d DU . .
O2 O 0.6647(5) 0.7356(7) 0.6474(2) 0.114(2) Uani 1 1 d DU . .
O3 O 0.4991(6) 0.8056(5) 0.68250(16) 0.101(2) Uani 1 1 d DU . .
O4 O 0.3356(5) 0.7370(7) 0.6471(2) 0.118(3) Uani 1 1 d DU . .
O5 O 0.3411(5) 0.5365(7) 0.6019(2) 0.126(3) Uani 1 1 d DU . .
O6 O 0.5018(7) 0.4923(7) 0.5623(2) 0.131(3) Uani 1 1 d DU . .
C15 C 0.7409(9) 0.5932(14) 0.6083(5) 0.150(5) Uani 1 1 d DU . .
H15A H 0.7512 0.6497 0.5872 0.179 Uiso 1 1 calc R . .
H15B H 0.7925 0.5375 0.6081 0.179 Uiso 1 1 calc R . .
C16 C 0.7375(7) 0.6511(11) 0.6445(4) 0.128(4) Uani 1 1 d DU . .
H16A H 0.7294 0.5930 0.6652 0.153 Uiso 1 1 calc R . .
H16B H 0.7971 0.6901 0.6489 0.153 Uiso 1 1 calc R . .
C17 C 0.6633(9) 0.7993(12) 0.6807(4) 0.146(5) Uani 1 1 d DU . .
H17A H 0.7187 0.8487 0.6818 0.175 Uiso 1 1 calc R . .
H17B H 0.6647 0.7467 0.7033 0.175 Uiso 1 1 calc R . .
C18 C 0.5803(9) 0.8725(11) 0.6828(4) 0.135(4) Uani 1 1 d DU . .
H18A H 0.5824 0.9192 0.7067 0.162 Uiso 1 1 calc R . .
H18B H 0.5795 0.9261 0.6605 0.162 Uiso 1 1 calc R . .
C19 C 0.4201(10) 0.8721(11) 0.6821(4) 0.136(4) Uani 1 1 d DU . .
H19A H 0.4212 0.9237 0.6593 0.163 Uiso 1 1 calc R . .
H19B H 0.4186 0.9209 0.7056 0.163 Uiso 1 1 calc R . .
C20 C 0.3371(9) 0.8007(12) 0.6807(4) 0.144(5) Uani 1 1 d DU . .
H20A H 0.3358 0.7483 0.7033 0.173 Uiso 1 1 calc R . .
H20B H 0.2819 0.8507 0.6819 0.173 Uiso 1 1 calc R . .
C21 C 0.2629(7) 0.6525(11) 0.6458(4) 0.132(4) Uani 1 1 d DU . .
H21A H 0.2033 0.6912 0.6502 0.159 Uiso 1 1 calc R . .
H21B H 0.2722 0.5956 0.6668 0.159 Uiso 1 1 calc R . .
C22 C 0.2602(9) 0.5932(14) 0.6092(5) 0.152(5) Uani 1 1 d DU . .
H22A H 0.2090 0.5370 0.6094 0.182 Uiso 1 1 calc R . .
H22B H 0.2483 0.6497 0.5883 0.182 Uiso 1 1 calc R . .
C23 C 0.3428(9) 0.4949(13) 0.5634(4) 0.146(5) Uani 1 1 d DU . .
H23A H 0.3443 0.5604 0.5451 0.175 Uiso 1 1 calc R . .
H23B H 0.2868 0.4489 0.5581 0.175 Uiso 1 1 calc R . .
C24 C 0.4213(10) 0.4261(12) 0.5587(4) 0.135(4) Uani 1 1 d DU . .
H24A H 0.4215 0.3641 0.5784 0.162 Uiso 1 1 calc R . .
H24B H 0.4197 0.3894 0.5328 0.162 Uiso 1 1 calc R . .
C25 C 0.5782(10) 0.4262(12) 0.5584(4) 0.144(5) Uani 1 1 d DU . .
H25A H 0.5796 0.3924 0.5321 0.173 Uiso 1 1 calc R . .
H25B H 0.5764 0.3622 0.5773 0.173 Uiso 1 1 calc R . .
C26 C 0.6571(9) 0.4920(13) 0.5644(4) 0.148(5) Uani 1 1 d DU . .
H26A H 0.7121 0.4435 0.5598 0.177 Uiso 1 1 calc R . .
H26B H 0.6583 0.5565 0.5456 0.177 Uiso 1 1 calc R . .
N3 N 0.4989(7) 0.2390(10) 0.4077(3) 0.045(2) Uani 0.766(7) 1 d PU B 1
H3A H 0.4459 0.2538 0.3964 0.054 Uiso 0.766(7) 1 calc PR B 1
H3B H 0.5505 0.2493 0.3949 0.054 Uiso 0.766(7) 1 calc PR B 1
N4 N 0.4998(9) 0.0728(8) 0.5938(3) 0.106(4) Uani 0.766(7) 1 d PU B 1
F5 F 0.6617(4) 0.1993(6) 0.44479(18) 0.087(2) Uani 0.766(7) 1 d PU B 1
F6 F 0.6617(4) 0.1320(5) 0.51820(17) 0.086(2) Uani 0.766(7) 1 d PU B 1
F7 F 0.3393(5) 0.1301(7) 0.5184(2) 0.090(2) Uani 0.766(7) 1 d PU B 1
C8 C 0.5010(7) 0.2024(10) 0.4428(3) 0.048(2) Uani 0.766(7) 1 d PU B 1
F8 F 0.3388(3) 0.1986(6) 0.44517(18) 0.091(2) Uani 0.766(7) 1 d PU B 1
C9 C 0.5802(7) 0.1877(9) 0.4624(3) 0.048(2) Uani 0.766(7) 1 d PU B 1
C10 C 0.5806(7) 0.1532(8) 0.5021(3) 0.061(2) Uani 0.766(7) 1 d PU B 1
C11 C 0.5000(6) 0.1340(7) 0.5221(2) 0.056(2) Uani 0.766(7) 1 d PU B 1
C12 C 0.4198(7) 0.1523(8) 0.5015(3) 0.064(3) Uani 0.766(7) 1 d PU B 1
C13 C 0.4196(5) 0.1852(6) 0.46387(19) 0.0571(17) Uani 0.766(7) 1 d PU B 1
C14 C 0.4998(11) 0.1092(17) 0.5610(4) 0.081(4) Uani 0.766(7) 1 d PU B 1
N3A N 0.508(5) 0.259(7) 0.403(2) 0.13(3) Uiso 0.234(7) 1 d P . 2
N4A N 0.419(4) -0.163(4) 0.5271(18) 0.090 Uiso 0.234(7) 1 d PD . 2
F5A F 0.5534(16) 0.029(2) 0.3929(7) 0.109(8) Uiso 0.234(7) 1 d P B 2
F6A F 0.498(3) -0.143(3) 0.4293(12) 0.112(14) Uiso 0.234(7) 1 d P B 2
F7A F 0.324(5) 0.159(7) 0.506(2) 0.23(3) Uiso 0.234(7) 1 d PU B 2
F8A F 0.3881(19) 0.286(2) 0.4747(8) 0.121(9) Uiso 0.234(7) 1 d P B 2
C13A C 0.4196(5) 0.1852(6) 0.46387(19) 0.0571(17) Uani 0.234(7) 1 d PDU B 2
C12A C 0.374(3) 0.088(3) 0.4797(14) 0.106(13) Uiso 0.234(7) 1 d PD B 2
C11A C 0.398(3) -0.029(3) 0.4754(11) 0.105(13) Uiso 0.234(7) 1 d PD B 2
C10A C 0.453(3) -0.038(4) 0.4423(12) 0.116(15) Uiso 0.234(7) 1 d PD B 2
C9A C 0.4989(17) 0.054(2) 0.4247(8) 0.050 Uiso 0.234(7) 1 d PD B 2
C8A C 0.488(3) 0.169(3) 0.4357(14) 0.09(2) Uiso 0.234(7) 1 d PD B 2
C14A C 0.376(3) -0.097(4) 0.5094(13) 0.105(14) Uiso 0.234(7) 1 d PD 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
N1 C1 1.28(3) . ?
N2 C7 1.02(3) . ?
C1 C2 1.43(2) . ?
C1 C6 1.403(18) . ?
C2 F1 1.321(13) . ?
C2 C3 1.378(16) . ?
C3 F2 1.301(19) . ?
C3 C4 1.409(18) . ?
C4 C5 1.411(17) . ?
C4 C7 1.42(2) . ?
C5 C6 1.335(13) . ?
C5 F3 1.31(3) . ?
C6 F4 1.328(9) . ?
C1A N1A 1.18(3) . ?
C1A C2A 1.39(2) . ?
C2A F1A 1.343(13) . ?
C2A C3A 1.372(17) . ?
C3A F2A 1.33(2) . ?
C3A C4A 1.424(19) . ?
C4A C5A 1.374(18) . ?
C4A C7A 1.38(3) . ?
C5A F3A 1.40(3) . ?
C7A N2A 1.02(3) . ?
O1 C15 1.356(13) . ?
O1 C26 1.411(14) . ?
O2 C17 1.369(13) . ?
O2 C16 1.447(12) . ?
O3 C19 1.384(12) . ?
O3 C18 1.413(12) . ?
O4 C20 1.377(13) . ?
O4 C21 1.442(12) . ?
O5 C22 1.373(13) . ?
O5 C23 1.416(13) . ?
O6 C25 1.357(13) . ?
O6 C24 1.406(12) . ?
C15 C16 1.421(16) . ?
C17 C18 1.477(15) . ?
C19 C20 1.465(15) . ?
C21 C22 1.438(16) . ?
C23 C24 1.403(14) . ?
C25 C26 1.394(14) . ?
N3 C8 1.285(14) . ?
N4 C14 1.210(17) . ?
F5 C9 1.342(12) . ?
F6 C10 1.327(12) . ?
F7 C12 1.335(12) . ?
C8 C13 1.407(11) . ?
C8 C9 1.347(15) . ?
F8 C13 1.349(8) . ?
C9 C10 1.428(14) . ?
C10 C11 1.381(13) . ?
C11 C14 1.376(16) . ?
C11 C12 1.382(14) . ?
C12 C13 1.355(11) . ?
N3A N4A 2.86(10) 5_656 ?
N4A N3A 2.86(10) 5_656 ?
F5A C9A 1.39(3) . ?
F6A C10A 1.45(6) . ?
F7A C12A 1.41(8) . ?
C12A C11A 1.41(2) . ?
C11A C10A 1.40(2) . ?
C11A C14A 1.457(12) . ?
C10A C9A 1.40(2) . ?
C9A C8A 1.39(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.2(17) . . ?
N1 C1 C6 133.0(18) . . ?
C2 C1 C6 116.3(12) . . ?
C1 C2 F1 118.4(10) . . ?
C1 C2 C3 122.0(12) . . ?
F1 C2 C3 119.6(10) . . ?
F2 C3 C2 120.3(11) . . ?
F2 C3 C4 118.7(10) . . ?
C2 C3 C4 120.5(12) . . ?
C5 C4 C7 124.0(15) . . ?
C5 C4 C3 115.7(10) . . ?
C7 C4 C3 120.2(15) . . ?
C4 C5 C6 124.5(10) . . ?
C4 C5 F3 116.7(15) . . ?
C6 C5 F3 118.8(15) . . ?
F4 C6 C5 121.1(8) . . ?
F4 C6 C1 118.1(8) . . ?
C5 C6 C1 120.8(10) . . ?
N2 C7 C4 146(3) . . ?
N1A C1A C2A 113.3(19) . . ?
F1A C2A C1A 118.4(11) . . ?
F1A C2A C3A 117.9(11) . . ?
C1A C2A C3A 123.7(12) . . ?
F2A C3A C2A 120.9(12) . . ?
F2A C3A C4A 119.1(10) . . ?
C2A C3A C4A 119.9(12) . . ?
C5A C4A C7A 119.9(17) . . ?
C5A C4A C3A 116.3(10) . . ?
C7A C4A C3A 123.8(17) . . ?
C4A C5A F3A 119.0(14) . . ?
N2A C7A C4A 155(3) . . ?
C15 O1 C26 110.2(10) . . ?
C17 O2 C16 115.9(9) . . ?
C19 O3 C18 112.9(9) . . ?
C20 O4 C21 113.7(9) . . ?
C22 O5 C23 110.7(11) . . ?
C25 O6 C24 111.4(10) . . ?
O1 C15 C16 109.2(12) . . ?
O2 C16 C15 114.1(10) . . ?
O2 C17 C18 111.4(11) . . ?
O3 C18 C17 111.5(10) . . ?
O3 C19 C20 111.8(10) . . ?
O4 C20 C19 110.0(10) . . ?
O4 C21 C22 111.9(10) . . ?
O5 C22 C21 111.6(12) . . ?
O5 C23 C24 108.6(11) . . ?
O6 C24 C23 110.9(11) . . ?
O6 C25 C26 110.5(12) . . ?
O1 C26 C25 111.5(11) . . ?
N3 C8 C13 121.2(9) . . ?
N3 C8 C9 122.4(9) . . ?
C13 C8 C9 116.1(8) . . ?
F5 C9 C10 117.5(9) . . ?
F5 C9 C8 121.0(8) . . ?
C10 C9 C8 121.4(9) . . ?
F6 C10 C9 117.2(9) . . ?
F6 C10 C11 121.0(8) . . ?
C9 C10 C11 121.6(9) . . ?
C14 C11 C12 122.2(10) . . ?
C14 C11 C10 121.8(10) . . ?
C12 C11 C10 115.7(8) . . ?
F7 C12 C13 118.4(9) . . ?
F7 C12 C11 118.9(8) . . ?
C13 C12 C11 122.6(8) . . ?
F8 C13 C12 119.5(7) . . ?
F8 C13 C8 117.9(7) . . ?
C12 C13 C8 122.5(8) . . ?
N4 C14 C11 171.7(19) . . ?
C11A C12A F7A 139(4) . . ?
C12A C11A C10A 108(4) . . ?
C12A C11A C14A 112(3) . . ?
C10A C11A C14A 138(4) . . ?
F6A C10A C9A 107(3) . . ?
F6A C10A C11A 125(3) . . ?
C9A C10A C11A 125(4) . . ?
C8A C9A F5A 119(2) . . ?
C8A C9A C10A 124(3) . . ?
F5A C9A C10A 117(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.109
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_2Fcr-m914
_database_code_depnum_ccdc_archive 'CCDC 1580790'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-amino-2,3,5,6-tetrafluoropyridine and 18-crown-6 2:1 associate
;
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         '2(C5 H2 F4 N2), C12 H24 O6'
_chemical_formula_sum            'C22 H28 F8 N4 O6'
_chemical_formula_weight         596.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   18.5893(6)
_cell_length_b                   9.6007(3)
_cell_length_c                   16.5096(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.4540(10)
_cell_angle_gamma                90.00
_cell_volume                     2637.95(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8123
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8908
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24923
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.52
_reflns_number_total             3041
_reflns_number_gt                2345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0491P)²+4.1527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3041
_refine_ls_number_parameters     208
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.91222(9) 0.28910(16) -0.03473(11) 0.0479(4) Uani 1 1 d . . .
O2 O 1.01436(11) 0.30480(19) 0.14764(13) 0.0694(6) Uani 1 1 d D . .
O3 O 1.12418(10) 0.54377(17) 0.18561(11) 0.0532(4) Uani 1 1 d D . .
C6 C 0.9336(2) 0.1692(3) 0.0239(2) 0.0654(8) Uani 1 1 d . . .
H6A H 0.9322 0.0844 -0.0109 0.078 Uiso 1 1 calc R B .
H6B H 0.8943 0.1572 0.0488 0.078 Uiso 1 1 calc R . .
C7 C 1.0147(2) 0.1880(3) 0.0985(2) 0.0754(9) Uani 1 1 d D B .
H7A H 1.0302 0.1049 0.1381 0.090 Uiso 1 1 calc R A 2
H7B H 1.0541 0.2002 0.0739 0.090 Uiso 1 1 calc R A 2
C8 C 1.0842(2) 0.3428(4) 0.2337(2) 0.0472(12) Uani 0.672(8) 1 d PD B 1
H8A H 1.1052 0.2585 0.2716 0.057 Uiso 0.672(8) 1 calc PR B 1
H8B H 1.0672 0.4098 0.2674 0.057 Uiso 0.672(8) 1 calc PR B 1
C9 C 1.1486(2) 0.4062(4) 0.2155(3) 0.0459(11) Uani 0.672(8) 1 d PD B 1
H9A H 1.2002 0.4067 0.2713 0.055 Uiso 0.672(8) 1 calc PR B 1
H9B H 1.1559 0.3525 0.1685 0.055 Uiso 0.672(8) 1 calc PR B 1
C8A C 1.1040(5) 0.2915(9) 0.1939(6) 0.062(3) Uani 0.328(8) 1 d PD B 2
H8A1 H 1.1220 0.2098 0.2347 0.075 Uiso 0.328(8) 1 calc PR B 2
H8A2 H 1.1271 0.2873 0.1503 0.075 Uiso 0.328(8) 1 calc PR B 2
C9A C 1.1231(6) 0.4266(10) 0.2454(6) 0.062(3) Uani 0.328(8) 1 d PD B 2
H9A1 H 1.1762 0.4197 0.2988 0.074 Uiso 0.328(8) 1 calc PR B 2
H9A2 H 1.0822 0.4456 0.2670 0.074 Uiso 0.328(8) 1 calc PR B 2
C10 C 1.18391(14) 0.5960(3) 0.16089(17) 0.0614(8) Uani 1 1 d D B .
H10A H 1.1921 0.5287 0.1203 0.074 Uiso 1 1 calc R . .
H10B H 1.2356 0.6071 0.2158 0.074 Uiso 1 1 calc R . .
C11 C 1.15867(16) 0.7307(3) 0.11490(17) 0.0608(7) Uani 1 1 d . . .
H11A H 1.1491 0.7978 0.1546 0.073 Uiso 1 1 calc R B .
H11B H 1.2013 0.7688 0.1008 0.073 Uiso 1 1 calc R . .
N1 N 0.79180(13) 0.7879(2) 0.13902(13) 0.0500(5) Uani 1 1 d . . .
F1 F 0.87924(12) 0.96764(16) 0.18547(12) 0.0761(5) Uani 1 1 d . . .
C1 C 0.86025(16) 0.8400(2) 0.14836(15) 0.0482(6) Uani 1 1 d . . .
F2 F 0.98179(9) 0.83717(15) 0.13505(11) 0.0638(4) Uani 1 1 d . . .
C2 C 0.91257(13) 0.7755(2) 0.12306(15) 0.0412(5) Uani 1 1 d . . .
N2 N 0.94243(12) 0.5774(2) 0.05419(15) 0.0464(5) Uani 1 1 d . . .
H2B H 0.9888(18) 0.606(3) 0.0713(19) 0.059(8) Uiso 1 1 d . . .
H2A H 0.9341(16) 0.494(3) 0.0419(18) 0.053(7) Uiso 1 1 d . . .
C3 C 0.89507(12) 0.6434(2) 0.08352(13) 0.0352(4) Uani 1 1 d . . .
F3 F 0.79909(8) 0.46160(14) 0.03751(10) 0.0540(4) Uani 1 1 d . . .
C4 C 0.82206(12) 0.5895(2) 0.07419(14) 0.0378(4) Uani 1 1 d . . .
F4 F 0.70513(9) 0.60765(19) 0.09252(11) 0.0662(4) Uani 1 1 d . . .
C5 C 0.77498(13) 0.6640(3) 0.10250(15) 0.0446(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.404(3) 5_765 ?
O1 C6 1.442(3) . ?
O2 C7 1.386(4) . ?
O2 C8 1.481(4) . ?
O2 C8A 1.498(8) . ?
O3 C9 1.413(4) . ?
O3 C10 1.434(3) . ?
O3 C9A 1.502(10) . ?
C6 C7 1.472(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8A 1.974(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.487(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8A C9A 1.504(13) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10 C11 1.467(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O1 1.404(3) 5_765 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 C5 1.306(3) . ?
N1 C1 1.311(3) . ?
F1 C1 1.345(3) . ?
C1 C2 1.366(3) . ?
F2 C2 1.348(3) . ?
C2 C3 1.397(3) . ?
N2 C3 1.338(3) . ?
N2 H2B 0.83(3) . ?
N2 H2A 0.83(3) . ?
C3 C4 1.396(3) . ?
F3 C4 1.351(2) . ?
C4 C5 1.364(3) . ?
F4 C5 1.348(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C6 112.8(2) 5_765 . ?
C7 O2 C8 122.0(3) . . ?
C7 O2 C8A 86.3(4) . . ?
C8 O2 C8A 39.7(4) . . ?
C9 O3 C10 104.9(3) . . ?
C9 O3 C9A 33.5(3) . . ?
C10 O3 C9A 133.5(4) . . ?
O1 C6 C7 109.6(2) . . ?
O1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
O1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O2 C7 C6 108.6(2) . . ?
O2 C7 C8A 49.2(3) . . ?
C6 C7 C8A 156.0(3) . . ?
O2 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C8A C7 H7A 89.1 . . ?
O2 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C8A C7 H7B 75.8 . . ?
H7A C7 H7B 108.3 . . ?
O2 C8 C9 110.4(3) . . ?
O2 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
O2 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O3 C9 C8 106.9(4) . . ?
O3 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
C9A C8A O2 98.3(7) . . ?
C9A C8A C7 142.0(7) . . ?
O2 C8A C7 44.5(3) . . ?
C9A C8A H8A1 112.1 . . ?
O2 C8A H8A1 112.1 . . ?
C7 C8A H8A1 93.0 . . ?
C9A C8A H8A2 112.1 . . ?
O2 C8A H8A2 112.1 . . ?
C7 C8A H8A2 83.2 . . ?
H8A1 C8A H8A2 109.8 . . ?
C8A C9A O3 110.1(8) . . ?
C8A C9A H9A1 109.6 . . ?
O3 C9A H9A1 109.6 . . ?
C8A C9A H9A2 109.6 . . ?
O3 C9A H9A2 109.6 . . ?
H9A1 C9A H9A2 108.2 . . ?
O3 C10 C11 110.3(2) . . ?
O3 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O3 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 C10 108.5(2) 5_765 . ?
O1 C11 H11A 110.0 5_765 . ?
C10 C11 H11A 110.0 . . ?
O1 C11 H11B 110.0 5_765 . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C5 N1 C1 114.96(19) . . ?
N1 C1 F1 116.5(2) . . ?
N1 C1 C2 125.2(2) . . ?
F1 C1 C2 118.3(2) . . ?
F2 C2 C1 121.3(2) . . ?
F2 C2 C3 118.39(18) . . ?
C1 C2 C3 120.3(2) . . ?
C3 N2 H2B 118(2) . . ?
C3 N2 H2A 117.9(19) . . ?
H2B N2 H2A 117(3) . . ?
N2 C3 C4 123.23(19) . . ?
N2 C3 C2 123.1(2) . . ?
C4 C3 C2 113.66(18) . . ?
F3 C4 C5 120.49(19) . . ?
F3 C4 C3 118.98(18) . . ?
C5 C4 C3 120.5(2) . . ?
N1 C5 F4 116.2(2) . . ?
N1 C5 C4 125.3(2) . . ?
F4 C5 C4 118.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 C6 C7 170.4(2) 5_765 . . . ?
C8 O2 C7 C6 172.5(3) . . . . ?
C8A O2 C7 C6 -169.2(4) . . . . ?
C8 O2 C7 C8A -18.3(4) . . . . ?
O1 C6 C7 O2 61.1(3) . . . . ?
O1 C6 C7 C8A 40.8(11) . . . . ?
C7 O2 C8 C9 76.5(4) . . . . ?
C8A O2 C8 C9 47.2(6) . . . . ?
C10 O3 C9 C8 -174.7(3) . . . . ?
C9A O3 C9 C8 32.9(6) . . . . ?
O2 C8 C9 O3 76.2(4) . . . . ?
C7 O2 C8A C9A 171.4(7) . . . . ?
C8 O2 C8A C9A -33.2(5) . . . . ?
C8 O2 C8A C7 155.4(5) . . . . ?
O2 C7 C8A C9A -13.9(12) . . . . ?
C6 C7 C8A C9A 12(2) . . . . ?
C6 C7 C8A O2 25.8(11) . . . . ?
O2 C8A C9A O3 -83.2(9) . . . . ?
C7 C8A C9A O3 -73.3(16) . . . . ?
C9 O3 C9A C8A -45.4(7) . . . . ?
C10 O3 C9A C8A -83.5(8) . . . . ?
C9 O3 C10 C11 170.9(2) . . . . ?
C9A O3 C10 C11 -168.4(5) . . . . ?
O3 C10 C11 O1 -62.6(3) . . . 5_765 ?
C5 N1 C1 F1 179.8(2) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
N1 C1 C2 F2 179.8(2) . . . . ?
F1 C1 C2 F2 0.3(3) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
F1 C1 C2 C3 -179.44(19) . . . . ?
F2 C2 C3 N2 -2.4(3) . . . . ?
C1 C2 C3 N2 177.3(2) . . . . ?
F2 C2 C3 C4 -179.90(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
N2 C3 C4 F3 3.1(3) . . . . ?
C2 C3 C4 F3 -179.39(18) . . . . ?
N2 C3 C4 C5 -177.6(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C1 N1 C5 F4 179.7(2) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
F3 C4 C5 N1 179.7(2) . . . . ?
C3 C4 C5 N1 0.4(3) . . . . ?
F3 C4 C5 F4 -0.4(3) . . . . ?
C3 C4 C5 F4 -179.72(19) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_2Ccr-m926
_database_code_depnum_ccdc_archive 'CCDC 1580788'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,3,5,6-tetrafluoroaniline and 18-crown-6 2:1 associate 
;
_chemical_name_common            ?
_chemical_melting_point          363
_chemical_formula_moiety         '2(C6 H3 F4 N), C12 H24 O6'
_chemical_formula_sum            'C24 H30 F8 N2 O6'
_chemical_formula_weight         594.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.5736(3)
_cell_length_b                   9.9242(4)
_cell_length_c                   10.1058(5)
_cell_angle_alpha                117.412(2)
_cell_angle_beta                 103.573(2)
_cell_angle_gamma                100.167(2)
_cell_volume                     700.49(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8700
_exptl_absorpt_correction_T_max  0.9118
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19988
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3199
_reflns_number_gt                2451
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0966P)²+0.2718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.141(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3199
_refine_ls_number_parameters     188
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0654(2) -0.21229(14) 0.58569(16) 0.0838(5) Uani 1 1 d . . .
F2 F 0.2232(2) -0.16656(18) 0.40531(19) 0.0971(5) Uani 1 1 d . . .
F3 F 0.3456(3) 0.39086(18) 0.7267(2) 0.1167(7) Uani 1 1 d . . .
F4 F 0.1907(2) 0.34573(14) 0.91003(16) 0.0811(4) Uani 1 1 d . . .
O1 O -0.26986(18) 1.13116(19) 0.99242(17) 0.0675(4) Uani 1 1 d . . .
O2 O -0.32987(17) 0.79850(18) 0.75003(18) 0.0679(4) Uani 1 1 d . . .
O3 O 0.06759(19) 1.32248(17) 1.17623(17) 0.0689(4) Uani 1 1 d . . .
N1 N 0.0388(3) 0.0435(2) 0.8448(2) 0.0752(6) Uani 1 1 d D . .
H3 H 0.044(4) 0.124(2) 0.929(2) 0.113 Uiso 1 1 d D . .
H1 H 0.002(4) -0.0483(19) 0.831(4) 0.113 Uiso 1 1 d D . .
C1 C 0.1241(2) 0.0658(2) 0.7551(2) 0.0481(4) Uani 1 1 d . . .
C2 C 0.1368(2) -0.0606(2) 0.6234(2) 0.0531(4) Uani 1 1 d . . .
C3 C 0.2177(3) -0.0367(2) 0.5306(2) 0.0617(5) Uani 1 1 d . . .
C4 C 0.2904(3) 0.1138(3) 0.5616(3) 0.0735(6) Uani 1 1 d . . .
H2 H 0.3448 0.1302 0.4981 0.088 Uiso 1 1 calc R . .
C5 C 0.2788(3) 0.2386(2) 0.6902(3) 0.0677(6) Uani 1 1 d . . .
C6 C 0.1990(2) 0.2175(2) 0.7850(2) 0.0532(4) Uani 1 1 d . . .
C7 C -0.0677(4) 1.3840(3) 1.1940(3) 0.0773(6) Uani 1 1 d . . .
H5 H -0.0304 1.4974 1.2303 0.093 Uiso 1 1 calc R . .
H4 H -0.1048 1.3723 1.2729 0.093 Uiso 1 1 calc R . .
C8 C -0.2097(3) 1.2937(3) 1.0375(3) 0.0767(6) Uani 1 1 d . . .
H14 H -0.3006 1.3394 1.0453 0.092 Uiso 1 1 calc R . .
H13 H -0.1709 1.3010 0.9576 0.092 Uiso 1 1 calc R . .
C9 C -0.4028(3) 1.0384(3) 0.8432(3) 0.0815(7) Uani 1 1 d . . .
H9A H -0.3661 1.0485 0.7634 0.098 Uiso 1 1 calc R . .
H9B H -0.4991 1.0766 0.8486 0.098 Uiso 1 1 calc R . .
C10 C -0.4533(3) 0.8688(4) 0.7975(3) 0.0852(8) Uani 1 1 d . . .
H11 H -0.4656 0.8619 0.8874 0.102 Uiso 1 1 calc R . .
H12 H -0.5623 0.8097 0.7101 0.102 Uiso 1 1 calc R . .
C11 C 0.3594(3) 1.3543(3) 1.2724(3) 0.0766(6) Uani 1 1 d . . .
H7 H 0.3652 1.3497 1.1758 0.092 Uiso 1 1 calc R . .
H8 H 0.4674 1.4263 1.3585 0.092 Uiso 1 1 calc R . .
C12 C 0.2206(3) 1.4173(3) 1.3124(3) 0.0785(7) Uani 1 1 d . . .
H6 H 0.2062 1.4116 1.4023 0.094 Uiso 1 1 calc R . .
H9 H 0.2490 1.5288 1.3416 0.094 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.350(2) . ?
F2 C3 1.347(2) . ?
F3 C5 1.353(2) . ?
F4 C6 1.347(2) . ?
O1 C9 1.402(3) . ?
O1 C8 1.412(3) . ?
O2 C11 1.391(3) 2_577 ?
O2 C10 1.424(3) . ?
O3 C7 1.413(3) . ?
O3 C12 1.423(3) . ?
N1 C1 1.358(2) . ?
N1 H3 0.842(10) . ?
N1 H1 0.843(10) . ?
C1 C6 1.385(2) . ?
C1 C2 1.391(3) . ?
C2 C3 1.367(3) . ?
C3 C4 1.367(3) . ?
C4 C5 1.361(3) . ?
C4 H2 0.9300 . ?
C5 C6 1.368(3) . ?
C7 C8 1.481(4) . ?
C7 H5 0.9700 . ?
C7 H4 0.9700 . ?
C8 H14 0.9700 . ?
C8 H13 0.9700 . ?
C9 C10 1.472(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H11 0.9700 . ?
C10 H12 0.9700 . ?
C11 O2 1.391(3) 2_577 ?
C11 C12 1.492(4) . ?
C11 H7 0.9700 . ?
C11 H8 0.9700 . ?
C12 H6 0.9700 . ?
C12 H9 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
C9 O1 C8 111.77(18) . . ?
C11 O2 C10 112.92(19) 2_577 . ?
C7 O3 C12 113.24(18) . . ?
C1 N1 H3 120(2) . . ?
C1 N1 H1 121(2) . . ?
H3 N1 H1 118(3) . . ?
N1 C1 C6 121.81(17) . . ?
N1 C1 C2 123.02(16) . . ?
C6 C1 C2 115.12(15) . . ?
F1 C2 C3 118.97(17) . . ?
F1 C2 C1 118.61(15) . . ?
C3 C2 C1 122.41(16) . . ?
F2 C3 C4 120.13(18) . . ?
F2 C3 C2 118.18(18) . . ?
C4 C3 C2 121.69(18) . . ?
C3 C4 C5 116.46(18) . . ?
C3 C4 H2 121.8 . . ?
C5 C4 H2 121.8 . . ?
F3 C5 C4 119.81(18) . . ?
F3 C5 C6 117.35(19) . . ?
C4 C5 C6 122.83(18) . . ?
F4 C6 C5 120.07(16) . . ?
F4 C6 C1 118.44(16) . . ?
C5 C6 C1 121.49(17) . . ?
O3 C7 C8 108.61(18) . . ?
O3 C7 H5 110.0 . . ?
C8 C7 H5 110.0 . . ?
O3 C7 H4 110.0 . . ?
C8 C7 H4 110.0 . . ?
H5 C7 H4 108.3 . . ?
O1 C8 C7 109.04(17) . . ?
O1 C8 H14 109.9 . . ?
C7 C8 H14 109.9 . . ?
O1 C8 H13 109.9 . . ?
C7 C8 H13 109.9 . . ?
H14 C8 H13 108.3 . . ?
O1 C9 C10 109.5(2) . . ?
O1 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
O1 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 C9 110.81(19) . . ?
O2 C10 H11 109.5 . . ?
C9 C10 H11 109.5 . . ?
O2 C10 H12 109.5 . . ?
C9 C10 H12 109.5 . . ?
H11 C10 H12 108.1 . . ?
O2 C11 C12 110.33(18) 2_577 . ?
O2 C11 H7 109.6 2_577 . ?
C12 C11 H7 109.6 . . ?
O2 C11 H8 109.6 2_577 . ?
C12 C11 H8 109.6 . . ?
H7 C11 H8 108.1 . . ?
O3 C12 C11 108.55(18) . . ?
O3 C12 H6 110.0 . . ?
C11 C12 H6 110.0 . . ?
O3 C12 H9 110.0 . . ?
C11 C12 H9 110.0 . . ?
H6 C12 H9 108.4 . . ?

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
N1 C1 C2 F1 -2.1(3) . . . . ?
C6 C1 C2 F1 -179.36(16) . . . . ?
N1 C1 C2 C3 177.5(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
F1 C2 C3 F2 -0.3(3) . . . . ?
C1 C2 C3 F2 -179.85(18) . . . . ?
F1 C2 C3 C4 179.13(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
F2 C3 C4 C5 179.8(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 F3 -179.0(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
F3 C5 C6 F4 -0.7(3) . . . . ?
C4 C5 C6 F4 -179.6(2) . . . . ?
F3 C5 C6 C1 178.82(19) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
N1 C1 C6 F4 2.2(3) . . . . ?
C2 C1 C6 F4 179.57(16) . . . . ?
N1 C1 C6 C5 -177.3(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C12 O3 C7 C8 170.36(19) . . . . ?
C9 O1 C8 C7 -178.86(19) . . . . ?
O3 C7 C8 O1 63.7(3) . . . . ?
C8 O1 C9 C10 176.47(18) . . . . ?
C11 O2 C10 C9 171.43(19) 2_577 . . . ?
O1 C9 C10 O2 -74.0(2) . . . . ?
C7 O3 C12 C11 -172.52(19) . . . . ?
O2 C11 C12 O3 -67.1(2) 2_577 . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: t-BuOMe'
