# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

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

data_compound-340K
_database_code_depnum_ccdc_archive 'CCDC 1025090'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 F3 N O2'
_chemical_formula_weight         213.20

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/m

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

_cell_length_a                   18.1351(16)
_cell_length_b                   6.6817(6)
_cell_length_c                   9.0685(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.199(7)
_cell_angle_gamma                90.00
_cell_volume                     1095.91(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    340(2)
_cell_measurement_reflns_used    1071
_cell_measurement_theta_min      3.91
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9877
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   'CrysAlis RED'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      340(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2987
_diffrn_reflns_av_R_equivalents  0.0091
_diffrn_reflns_av_sigmaI/netI    0.0107
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.91
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1071
_reflns_number_gt                658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD'
_computing_cell_refinement       'CrysAlis RED'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL V.5.0 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.2000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1071
_refine_ls_number_parameters     91
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.1154
_refine_ls_wR_factor_ref         0.3855
_refine_ls_wR_factor_gt          0.3411
_refine_ls_goodness_of_fit_ref   1.418
_refine_ls_restrained_S_all      1.636
_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
N1 N 0.31980(19) 0.0000 0.4636(4) 0.0902(14) Uani 1 2 d S . .
H1A H 0.3348 0.1100 0.5147 0.135 Uiso 1 1 d R . .
H1B H 0.2702 0.0000 0.4497 0.135 Uiso 1 2 d SR . .
C3 C 0.3531(3) 0.0000 0.3161(6) 0.1000(17) Uani 1 2 d S . .
H3A H 0.4071 0.0000 0.3329 0.120 Uiso 1 2 calc SR . .
C4 C 0.3298(3) 0.1820(6) 0.2290(5) 0.1293(18) Uani 1 1 d . . .
H4A H 0.3464 0.3006 0.2834 0.155 Uiso 1 1 calc R . .
H4B H 0.2762 0.1862 0.2159 0.155 Uiso 1 1 calc R . .
C5 C 0.3613(4) 0.1826(9) 0.0790(6) 0.152(2) Uani 1 1 d . . .
H5A H 0.3424 0.2978 0.0232 0.182 Uiso 1 1 calc R . .
H5B H 0.4147 0.1952 0.0922 0.182 Uiso 1 1 calc R . .
C6 C 0.3425(5) 0.0000 -0.0050(9) 0.153(3) Uani 1 2 d S . .
H6A H 0.3686 0.0000 -0.0946 0.184 Uiso 1 2 calc SR . .
H6B H 0.2899 0.0000 -0.0337 0.184 Uiso 1 2 calc SR . .
C1 C 0.3789(3) 0.5000 0.6310(5) 0.0911(16) Uani 1 2 d SD . .
C2 C 0.4474(4) 0.4230(9) 0.7071(7) 0.110(2) Uani 0.50 1 d PD . .
O2 O 0.3310(3) 0.4087(9) 0.5724(7) 0.1167(19) Uani 0.50 1 d PD . .
F1 F 0.5082(2) 0.5000 0.6651(7) 0.214(3) Uani 1 2 d SD . .
F2 F 0.4524(3) 0.5000 0.8429(5) 0.280(4) Uani 1 2 d SD . .
O1 O 0.3763(4) 0.6945(8) 0.6407(6) 0.135(2) Uani 0.50 1 d PD . .
F3 F 0.4533(4) 0.2316(11) 0.6759(11) 0.214(3) Uani 0.50 1 d PD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.078(2) 0.078(2) 0.113(3) 0.000 -0.0059(19) 0.000
C3 0.076(3) 0.096(3) 0.127(4) 0.000 -0.002(2) 0.000
C4 0.154(4) 0.090(3) 0.143(4) 0.007(2) 0.000(3) -0.003(2)
C5 0.165(4) 0.138(4) 0.151(5) 0.024(3) 0.011(3) -0.011(3)
C6 0.154(6) 0.155(7) 0.150(6) 0.000 0.007(5) 0.000
C1 0.092(3) 0.100(4) 0.080(3) 0.000 0.004(2) 0.000
C2 0.106(5) 0.115(5) 0.106(5) 0.020(3) -0.003(4) 0.014(4)
O2 0.078(3) 0.116(4) 0.154(4) -0.022(3) -0.007(3) 0.002(2)
F1 0.097(3) 0.297(7) 0.247(7) 0.000 0.007(4) 0.000
F2 0.192(6) 0.533(12) 0.107(3) 0.000 -0.040(3) 0.000
O1 0.165(6) 0.095(4) 0.139(5) 0.000(3) -0.027(4) 0.022(4)
F3 0.159(5) 0.148(5) 0.320(8) -0.051(5) -0.083(5) 0.061(4)

_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 C3 1.508(6) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.8999 . ?
C3 C4 1.494(5) 6 ?
C3 C4 1.494(5) . ?
C3 H3A 0.9800 . ?
C4 C5 1.514(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.466(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C5 1.466(7) 6 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 O2 1.159(5) 6_565 ?
C1 O2 1.159(5) . ?
C1 O1 1.303(5) . ?
C1 O1 1.303(5) 6_565 ?
C1 C2 1.470(7) . ?
C1 C2 1.470(7) 6_565 ?
C2 C2 1.029(12) 6_565 ?
C2 F1 1.298(7) . ?
C2 F3 1.316(7) . ?
C2 F2 1.331(7) . ?
C2 O1 1.591(9) 6_565 ?
O2 O1 1.208(7) 6_565 ?
O2 O2 1.221(12) 6_565 ?
F1 C2 1.298(7) 6_565 ?
F2 C2 1.331(7) 6_565 ?
O1 O2 1.208(7) 6_565 ?
O1 F3 1.494(10) 6_565 ?
O1 C2 1.591(9) 6_565 ?
F3 O1 1.494(10) 6_565 ?

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
C3 N1 H1A 109.4 . . ?
C3 N1 H1B 109.7 . . ?
H1A N1 H1B 109.5 . . ?
C4 C3 C4 108.9(5) 6 . ?
C4 C3 N1 110.6(3) 6 . ?
C4 C3 N1 110.6(3) . . ?
C4 C3 H3A 108.9 6 . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3A 108.9 . . ?
C3 C4 C5 111.5(4) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 112.1(5) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C5 112.7(7) . 6 ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 6 . ?
C5 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 6 . ?
H6A C6 H6B 107.8 . . ?
O2 C1 O2 63.6(7) 6_565 . ?
O2 C1 O1 58.4(3) 6_565 . ?
O2 C1 O1 121.8(6) . . ?
O2 C1 O1 121.8(6) 6_565 6_565 ?
O2 C1 O1 58.4(3) . 6_565 ?
O1 C1 O1 171.0(7) . 6_565 ?
O2 C1 C2 168.4(5) 6_565 . ?
O2 C1 C2 127.7(4) . . ?
O1 C1 C2 110.5(5) . . ?
O1 C1 C2 69.7(4) 6_565 . ?
O2 C1 C2 127.7(4) 6_565 6_565 ?
O2 C1 C2 168.4(5) . 6_565 ?
O1 C1 C2 69.7(4) . 6_565 ?
O1 C1 C2 110.5(5) 6_565 6_565 ?
C2 C1 C2 41.0(5) . 6_565 ?
C2 C2 F1 66.7(3) 6_565 . ?
C2 C2 F3 166.4(5) 6_565 . ?
F1 C2 F3 103.8(6) . . ?
C2 C2 F2 67.3(3) 6_565 . ?
F1 C2 F2 96.7(6) . . ?
F3 C2 F2 125.0(6) . . ?
C2 C2 C1 69.5(3) 6_565 . ?
F1 C2 C1 115.5(5) . . ?
F3 C2 C1 108.5(5) . . ?
F2 C2 C1 107.2(5) . . ?
C2 C2 O1 119.6(3) 6_565 6_565 ?
F1 C2 O1 140.1(6) . 6_565 ?
F3 C2 O1 61.0(4) . 6_565 ?
F2 C2 O1 122.6(6) . 6_565 ?
C1 C2 O1 50.2(3) . 6_565 ?
C1 O2 O1 66.8(3) . 6_565 ?
C1 O2 O2 58.2(3) . 6_565 ?
O1 O2 O2 124.8(3) 6_565 6_565 ?
C2 F1 C2 46.7(6) 6_565 . ?
C2 F2 C2 45.5(5) . 6_565 ?
O2 O1 C1 54.8(3) 6_565 . ?
O2 O1 F3 152.7(7) 6_565 6_565 ?
C1 O1 F3 107.8(5) . 6_565 ?
O2 O1 C2 114.5(5) 6_565 6_565 ?
C1 O1 C2 60.1(3) . 6_565 ?
F3 O1 C2 50.4(4) 6_565 6_565 ?
C2 F3 O1 68.6(4) . 6_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O2 0.90 1.93 2.797(6) 161.5 7_556
N1 H1B O2 0.90 1.93 2.797(6) 161.5 4_546
N1 H1A O1 0.90 1.86 2.749(6) 169.7 6_565
N1 H1A O2 0.90 2.07 2.905(5) 154.8 .
N1 H1A F3 0.90 2.64 3.358(7) 137.7 .

_diffrn_measured_fraction_theta_max 0.911
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.911
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.060


# comppound_340K RESULTS (APPEND TO CIF)

_vrf_PLAT029_compound-340K       
;
PROBLEM:ALERT:_diffrn_measured_fraction_theta_full Low ....... 0.911 Note
RESPONSE: Owing to poor data of the crystal at high temperature,  
we omitted part of poor reflection points to obtain the structure 
more precision, which result in poor data integrity 
;
# end Validation Reply Form 
####################################################################### 
# 
# 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_compound-100K
_database_code_depnum_ccdc_archive 'CCDC 1044765'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 F3 N O2'
_chemical_formula_weight         213.20

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   I2/a

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

_cell_length_a                   17.264(3)
_cell_length_b                   6.5684(2)
_cell_length_c                   17.7966(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.40(2)
_cell_angle_gamma                90.00
_cell_volume                     2017.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1977
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      25.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9867
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   'CrysAlis RED'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4468
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.02
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1977
_reflns_number_gt                1813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD'
_computing_cell_refinement       'CrysAlis RED'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL V.5.0 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0405P)²+1.7201P] 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         1977
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

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 0.22479(4) 0.71349(12) 0.17166(4) 0.0254(2) Uani 1 1 d . . .
F2 F 0.29303(4) 0.98578(11) 0.17059(5) 0.0284(2) Uani 1 1 d . . .
O1 O 0.41563(5) 0.77319(13) 0.21340(5) 0.0175(2) Uani 1 1 d . . .
O2 O 0.35649(5) 0.48202(13) 0.17785(5) 0.0220(2) Uani 1 1 d . . .
F3 F 0.29296(5) 0.78283(13) 0.07585(4) 0.0310(2) Uani 1 1 d . . .
N1 N 0.42674(6) 0.17875(15) 0.26513(5) 0.0148(2) Uani 1 1 d . . .
H1A H 0.4168 0.0555 0.2465 0.022 Uiso 1 1 calc R . .
H1B H 0.4778 0.1974 0.2687 0.022 Uiso 1 1 calc R . .
H1C H 0.4058 0.2727 0.2348 0.022 Uiso 1 1 calc R . .
C3 C 0.39271(7) 0.19687(17) 0.34166(7) 0.0153(3) Uani 1 1 d . . .
H3A H 0.3364 0.1792 0.3369 0.018 Uiso 1 1 calc R . .
C2 C 0.29274(7) 0.78987(17) 0.15077(7) 0.0155(3) Uani 1 1 d . . .
C1 C 0.36206(6) 0.66833(18) 0.18468(6) 0.0138(2) Uani 1 1 d . . .
C4 C 0.40961(7) 0.40789(18) 0.37342(7) 0.0184(3) Uani 1 1 d . . .
H4A H 0.3869 0.5103 0.3404 0.022 Uiso 1 1 calc R . .
H4B H 0.4652 0.4300 0.3762 0.022 Uiso 1 1 calc R . .
C6 C 0.40742(8) 0.2632(2) 0.50456(7) 0.0230(3) Uani 1 1 d . . .
H6A H 0.3827 0.2743 0.5527 0.028 Uiso 1 1 calc R . .
H6B H 0.4627 0.2822 0.5128 0.028 Uiso 1 1 calc R . .
C8 C 0.42546(7) 0.03100(18) 0.39298(7) 0.0172(3) Uani 1 1 d . . .
H8A H 0.4815 0.0420 0.3961 0.021 Uiso 1 1 calc R . .
H8B H 0.4123 -0.1016 0.3724 0.021 Uiso 1 1 calc R . .
C7 C 0.39228(8) 0.05169(19) 0.47153(7) 0.0217(3) Uani 1 1 d . . .
H7A H 0.3369 0.0269 0.4688 0.026 Uiso 1 1 calc R . .
H7B H 0.4156 -0.0502 0.5044 0.026 Uiso 1 1 calc R . .
C5 C 0.37613(8) 0.4285(2) 0.45177(7) 0.0233(3) Uani 1 1 d . . .
H5A H 0.3201 0.4188 0.4481 0.028 Uiso 1 1 calc R . .
H5B H 0.3893 0.5613 0.4723 0.028 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0131(4) 0.0306(4) 0.0326(4) 0.0029(3) 0.0005(3) -0.0030(3)
F2 0.0240(4) 0.0151(4) 0.0455(5) -0.0022(3) -0.0102(3) 0.0048(3)
O1 0.0124(4) 0.0170(4) 0.0229(5) -0.0020(3) -0.0020(3) 0.0006(3)
O2 0.0282(5) 0.0135(4) 0.0239(5) -0.0001(3) -0.0076(4) 0.0015(3)
F3 0.0331(5) 0.0445(5) 0.0153(4) 0.0060(3) -0.0009(3) 0.0143(4)
N1 0.0130(5) 0.0129(5) 0.0185(5) 0.0000(4) -0.0029(4) 0.0001(4)
C3 0.0122(5) 0.0155(6) 0.0182(6) 0.0008(5) -0.0005(4) 0.0005(4)
C2 0.0153(6) 0.0152(6) 0.0160(6) 0.0003(5) -0.0008(4) -0.0007(4)
C1 0.0145(6) 0.0149(6) 0.0120(5) 0.0008(4) 0.0017(4) 0.0011(4)
C4 0.0222(6) 0.0133(6) 0.0199(6) 0.0010(5) 0.0013(5) 0.0020(5)
C6 0.0256(7) 0.0251(7) 0.0182(6) -0.0002(5) 0.0011(5) 0.0027(5)
C8 0.0159(6) 0.0135(6) 0.0220(6) 0.0016(5) -0.0032(5) -0.0008(4)
C7 0.0231(6) 0.0206(6) 0.0212(6) 0.0057(5) -0.0017(5) -0.0004(5)
C5 0.0276(7) 0.0200(6) 0.0223(6) -0.0023(5) 0.0026(5) 0.0053(5)

_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 1.3370(14) . ?
F2 C2 1.3343(14) . ?
O1 C1 1.2521(14) . ?
O2 C1 1.2334(14) . ?
F3 C2 1.3342(14) . ?
N1 C3 1.5011(15) . ?
C3 C8 1.5217(16) . ?
C3 C4 1.5224(16) . ?
C2 C1 1.5486(16) . ?
C4 C5 1.5286(17) . ?
C6 C5 1.5260(18) . ?
C6 C7 1.5287(18) . ?
C8 C7 1.5296(17) . ?

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 C3 C8 109.87(9) . . ?
N1 C3 C4 109.47(9) . . ?
C8 C3 C4 111.35(10) . . ?
F3 C2 F2 107.31(10) . . ?
F3 C2 F1 106.78(10) . . ?
F2 C2 F1 106.62(10) . . ?
F3 C2 C1 110.52(9) . . ?
F2 C2 C1 113.35(10) . . ?
F1 C2 C1 111.91(9) . . ?
O2 C1 O1 129.88(11) . . ?
O2 C1 C2 114.54(10) . . ?
O1 C1 C2 115.56(10) . . ?
C3 C4 C5 110.25(10) . . ?
C5 C6 C7 110.82(10) . . ?
C3 C8 C7 110.06(10) . . ?
C6 C7 C8 111.59(10) . . ?
C4 C5 C6 111.25(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 1.95 2.8235(13) 168.6 1_545
N1 H1A F2 0.89 2.54 3.0944(13) 120.9 1_545
N1 H1B O1 0.89 1.93 2.8083(14) 170.9 4_545
N1 H1C O2 0.89 1.90 2.7856(13) 174.8 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.041
