# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_TFTPA-2H2O
_database_code_depnum_ccdc_archive 'CCDC 1044990'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-20 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 H6 F4 O6'
_chemical_formula_weight         274.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   8.5417(5)
_cell_length_b                   8.0442(5)
_cell_length_c                   7.4465(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.017(5)
_cell_angle_gamma                90.00
_cell_volume                     505.33(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1231
_cell_measurement_theta_min      6.0340
_cell_measurement_theta_max      71.0980

_exptl_crystal_description       block-like
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8133
_exptl_absorpt_correction_T_max  0.8408
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4098
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2808
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.24
_diffrn_reflns_theta_max         67.25
_reflns_number_total             904
_reflns_number_gt                810
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Olex-2
_computing_publication_material  Olex-2

_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)+(0.0768P)²+0.2276P] 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     SHELXL
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         904
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 0.59192(18) 0.9123(2) 0.3516(2) 0.0585(6) Uani 1 1 d . . .
F2 F 0.80748(16) 0.9452(2) 0.1374(2) 0.0564(5) Uani 1 1 d . . .
O1 O 0.1555(2) 1.0790(2) 0.2294(3) 0.0534(6) Uani 1 1 d . . .
O2 O 0.2755(2) 0.8480(2) 0.3450(3) 0.0513(6) Uani 1 1 d . . .
H2 H 0.2008 0.8445 0.4020 0.077 Uiso 1 1 calc R . .
O3 O 0.9629(2) 0.3024(3) 0.9914(3) 0.0598(6) Uani 1 1 d . . .
H3C H 1.0236 0.2362 1.0588 0.072 Uiso 1 1 d R . .
H3A H 0.9345 0.2588 0.8874 0.072 Uiso 1 1 d R . .
C1 C 0.2590(3) 0.9745(3) 0.2363(3) 0.0405(6) Uani 1 1 d . . .
C2 C 0.3841(3) 0.9846(3) 0.1154(3) 0.0382(6) Uani 1 1 d . . .
C3 C 0.5431(3) 0.9534(3) 0.1781(3) 0.0399(6) Uani 1 1 d . . .
C4 C 0.6555(3) 0.9693(3) 0.0653(3) 0.0396(6) Uani 1 1 d . . .

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 0.0493(9) 0.0862(13) 0.0404(9) 0.0083(8) 0.0083(6) 0.0079(8)
F2 0.0353(8) 0.0814(12) 0.0526(9) 0.0064(8) 0.0070(7) 0.0082(7)
O1 0.0518(11) 0.0541(12) 0.0602(12) 0.0085(9) 0.0269(9) 0.0130(8)
O2 0.0466(10) 0.0517(11) 0.0593(12) 0.0119(9) 0.0204(8) 0.0032(8)
O3 0.0576(12) 0.0725(14) 0.0540(11) 0.0062(9) 0.0236(9) 0.0203(10)
C1 0.0380(12) 0.0408(13) 0.0440(13) -0.0013(10) 0.0106(10) -0.0013(10)
C2 0.0376(12) 0.0338(12) 0.0453(13) -0.0033(9) 0.0133(10) -0.0001(9)
C3 0.0417(13) 0.0403(13) 0.0385(12) 0.0002(10) 0.0086(10) 0.0028(10)
C4 0.0325(11) 0.0393(13) 0.0473(14) -0.0020(10) 0.0068(9) 0.0027(9)

_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 C3 1.336(3) . ?
F2 C4 1.339(3) . ?
O1 C1 1.215(3) . ?
O2 C1 1.294(3) . ?
C1 C2 1.504(3) . ?
C2 C4 1.386(4) 3_675 ?
C2 C3 1.388(3) . ?
C3 C4 1.377(3) . ?
C4 C2 1.386(4) 3_675 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 125.3(2) . . ?
O1 C1 C2 121.2(2) . . ?
O2 C1 C2 113.5(2) . . ?
C4 C2 C3 116.9(2) 3_675 . ?
C4 C2 C1 120.5(2) 3_675 . ?
C3 C2 C1 122.6(2) . . ?
F1 C3 C4 118.1(2) . . ?
F1 C3 C2 120.7(2) . . ?
C4 C3 C2 121.1(2) . . ?
F2 C4 C3 117.8(2) . . ?
F2 C4 C2 120.2(2) . 3_675 ?
C3 C4 C2 122.0(2) . 3_675 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.054
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_DMTFTPA
_database_code_depnum_ccdc_archive 'CCDC 1044991'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 F4 O4'
_chemical_formula_weight         266.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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)/n  '

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

_cell_length_a                   6.332(6)
_cell_length_b                   4.701(5)
_cell_length_c                   17.423(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.605(15)
_cell_angle_gamma                90.00
_cell_volume                     516.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block-like
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_process_details   ?

_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  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4098
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2458
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.00
_reflns_number_total             988
_reflns_number_gt                844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Olex-2
_computing_publication_material  Olex-2

_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)+(0.1626P)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         988
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.1877
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
F2 F -0.20183(18) 0.9270(3) 0.12670(7) 0.0598(6) Uani 1 1 d . . .
O4 O 0.3788(2) 0.6589(4) 0.13614(10) 0.0618(6) Uani 1 1 d . . .
C9 C 0.1754(3) 0.6231(4) 0.12055(12) 0.0458(6) Uani 1 1 d . . .
C5 C -0.1020(3) 0.9549(4) 0.06401(12) 0.0447(6) Uani 1 1 d . . .
C6 C 0.0880(3) 0.8176(4) 0.05847(12) 0.0428(6) Uani 1 1 d . . .
O3 O 0.0694(2) 0.4616(4) 0.15222(12) 0.0691(7) Uani 1 1 d . . .
C4 C -0.1878(3) 1.1322(4) 0.00726(12) 0.0454(6) Uani 1 1 d . . .
C10 C 0.4822(4) 0.4789(7) 0.19515(16) 0.0719(9) Uani 1 1 d . . .
H10A H 0.4396 0.5338 0.2444 0.108 Uiso 1 1 calc R . .
H10B H 0.6332 0.4984 0.1956 0.108 Uiso 1 1 calc R . .
H10C H 0.4427 0.2845 0.1848 0.108 Uiso 1 1 calc R . .
F1 F -0.36486(18) 1.2686(3) 0.01874(8) 0.0658(6) Uani 1 1 d . . .

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
F2 0.0546(8) 0.0795(10) 0.0472(9) 0.0095(6) 0.0152(6) 0.0050(6)
O4 0.0487(9) 0.0763(11) 0.0579(12) 0.0215(8) -0.0069(7) -0.0002(7)
C9 0.0516(12) 0.0440(11) 0.0410(12) -0.0015(8) 0.0006(9) -0.0030(8)
C5 0.0453(10) 0.0516(11) 0.0376(11) -0.0018(8) 0.0063(8) -0.0040(8)
C6 0.0441(10) 0.0416(10) 0.0415(12) -0.0015(8) -0.0017(8) -0.0028(7)
O3 0.0659(11) 0.0665(11) 0.0726(13) 0.0225(9) -0.0043(9) -0.0134(8)
C4 0.0411(10) 0.0505(12) 0.0442(12) -0.0035(8) 0.0028(8) 0.0042(8)
C10 0.0639(13) 0.089(2) 0.0609(17) 0.0272(13) -0.0053(12) 0.0109(13)
F1 0.0559(9) 0.0863(11) 0.0566(10) 0.0059(7) 0.0128(7) 0.0276(7)

_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
F2 C5 1.321(3) . ?
O4 C9 1.301(3) . ?
O4 C10 1.439(3) . ?
C9 O3 1.185(3) . ?
C9 C6 1.481(3) . ?
C5 C4 1.365(3) . ?
C5 C6 1.377(3) . ?
C6 C4 1.381(3) 3_575 ?
C4 F1 1.323(2) . ?
C4 C6 1.381(3) 3_575 ?

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 O4 C10 116.44(19) . . ?
O3 C9 O4 125.4(2) . . ?
O3 C9 C6 123.19(19) . . ?
O4 C9 C6 111.35(17) . . ?
F2 C5 C4 118.08(19) . . ?
F2 C5 C6 120.23(19) . . ?
C4 C5 C6 121.6(2) . . ?
C5 C6 C4 116.85(19) . 3_575 ?
C5 C6 C9 120.3(2) . . ?
C4 C6 C9 122.84(19) 3_575 . ?
F1 C4 C5 118.02(19) . . ?
F1 C4 C6 120.35(18) . 3_575 ?
C5 C4 C6 121.53(19) . 3_575 ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.150
