# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1440457'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
#data_eca11 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'1,5-bis(trifluoromethyl)-3-[dimethylaminophenyl] methylene-2,4-pentanedione'
_chemical_formula_moiety         'C14 H11 F6 N O2'
_chemical_formula_sum            'C14 H11 F6 N O2'
_chemical_formula_weight         339.24

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   P21/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                   8.8400(5)
_cell_length_b                   15.0313(9)
_cell_length_c                   11.9237(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.1830(10)
_cell_angle_gamma                90.00
_cell_volume                     1477.33(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5767
_cell_measurement_theta_min      2.278
_cell_measurement_theta_max      22.836

_exptl_crystal_description       prism
_exptl_crystal_colour            'intense red'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_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 area detector'
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            18149
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         24.15
_reflns_number_total             2357
_reflns_number_gt                1893
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'

_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     
'w=1/[σ²(Fo²)+(0.0549P)²+0.5026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2357
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.22020(18) 0.40547(10) 0.58425(12) 0.0867(4) Uani 1 1 d . . .
F2 F 0.4707(2) 0.43314(12) 0.65172(15) 0.1129(6) Uani 1 1 d . . .
F3 F 0.3761(3) 0.32781(12) 0.52502(15) 0.1325(8) Uani 1 1 d . . .
F4 F 0.1579(2) 0.17716(10) 0.76587(13) 0.0941(5) Uani 1 1 d . . .
F5 F 0.3434(2) 0.09458(9) 0.88325(17) 0.1148(6) Uani 1 1 d . . .
F6 F 0.1849(2) 0.16534(11) 0.94965(15) 0.1114(6) Uani 1 1 d . . .
O1 O 0.4420(2) 0.22741(12) 0.71146(16) 0.0946(6) Uani 1 1 d . . .
O2 O 0.4876(3) 0.24539(13) 1.01279(16) 0.1003(6) Uani 1 1 d . . .
N1 N 0.1429(2) 0.56984(13) 1.21333(16) 0.0688(5) Uani 1 1 d . . .
C1 C 0.3645(3) 0.36684(17) 0.6202(2) 0.0753(6) Uani 1 1 d . . .
C2 C 0.3927(3) 0.30103(16) 0.7239(2) 0.0680(6) Uani 1 1 d . . .
C3 C 0.3615(2) 0.32591(13) 0.83038(18) 0.0592(5) Uani 1 1 d . . .
C4 C 0.3848(3) 0.24922(14) 0.9142(2) 0.0667(6) Uani 1 1 d . . .
C5 C 0.2664(3) 0.17060(15) 0.8760(2) 0.0747(6) Uani 1 1 d . . .
C6 C 0.3280(2) 0.41053(13) 0.85643(18) 0.0579(5) Uani 1 1 d . . .
H6 H 0.3326 0.4528 0.8008 0.069 Uiso 1 1 calc R . .
C7 C 0.2875(2) 0.44645(13) 0.95258(17) 0.0538(5) Uani 1 1 d . . .
C8 C 0.2652(3) 0.53853(13) 0.95480(18) 0.0618(5) Uani 1 1 d . . .
H8 H 0.2819 0.5731 0.8957 0.074 Uiso 1 1 calc R . .
C9 C 0.2202(3) 0.57971(14) 1.03946(19) 0.0635(5) Uani 1 1 d . . .
H9 H 0.2085 0.6412 1.0374 0.076 Uiso 1 1 calc R . .
C10 C 0.1910(2) 0.53062(14) 1.13021(17) 0.0560(5) Uani 1 1 d . . .
C11 C 0.2127(3) 0.43799(15) 1.12839(19) 0.0694(6) Uani 1 1 d . . .
H11 H 0.1950 0.4031 1.1869 0.083 Uiso 1 1 calc R . .
C12 C 0.2588(3) 0.39809(14) 1.04387(19) 0.0682(6) Uani 1 1 d . . .
H12 H 0.2718 0.3366 1.0463 0.082 Uiso 1 1 calc R . .
C13 C 0.1246(3) 0.66546(17) 1.2163(2) 0.0892(8) Uani 1 1 d . . .
H13A H 0.2286 0.6933 1.2357 0.134 Uiso 1 1 calc R . .
H13B H 0.0799 0.6806 1.2762 0.134 Uiso 1 1 calc R . .
H13C H 0.0531 0.6858 1.1390 0.134 Uiso 1 1 calc R . .
C14 C 0.1189(4) 0.5185(2) 1.3088(2) 0.0925(8) Uani 1 1 d . . .
H14A H 0.0482 0.4692 1.2746 0.139 Uiso 1 1 calc R . .
H14B H 0.0709 0.5557 1.3525 0.139 Uiso 1 1 calc R . .
H14C H 0.2216 0.4967 1.3625 0.139 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 C1 1.324(3) . ?
F2 C1 1.327(3) . ?
F3 C1 1.314(3) . ?
F4 C5 1.320(3) . ?
F5 C5 1.317(3) . ?
F6 C5 1.324(3) . ?
O1 C2 1.218(3) . ?
O2 C4 1.200(3) . ?
N1 C10 1.347(2) . ?
N1 C13 1.448(3) . ?
N1 C14 1.453(3) . ?
C1 C2 1.532(3) . ?
C2 C3 1.442(3) . ?
C3 C6 1.367(3) . ?
C3 C4 1.490(3) . ?
C4 C5 1.535(3) . ?
C6 C7 1.425(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.406(3) . ?
C8 C9 1.360(3) . ?
C9 C10 1.408(3) . ?
C10 C11 1.407(3) . ?
C11 C12 1.356(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
C10 N1 C13 121.34(19) . . ?
C10 N1 C14 121.2(2) . . ?
C13 N1 C14 117.30(19) . . ?
F3 C1 F1 106.4(2) . . ?
F3 C1 F2 108.2(2) . . ?
F1 C1 F2 105.2(2) . . ?
F3 C1 C2 111.6(2) . . ?
F1 C1 C2 113.66(19) . . ?
F2 C1 C2 111.4(2) . . ?
O1 C2 C3 122.3(2) . . ?
O1 C2 C1 116.7(2) . . ?
C3 C2 C1 121.1(2) . . ?
C6 C3 C2 124.56(19) . . ?
C6 C3 C4 123.81(18) . . ?
C2 C3 C4 111.42(18) . . ?
O2 C4 C3 124.5(2) . . ?
O2 C4 C5 116.6(2) . . ?
C3 C4 C5 118.85(19) . . ?
F5 C5 F4 107.6(2) . . ?
F5 C5 F6 107.3(2) . . ?
F4 C5 F6 106.9(2) . . ?
F5 C5 C4 111.5(2) . . ?
F4 C5 C4 114.19(18) . . ?
F6 C5 C4 109.01(19) . . ?
C3 C6 C7 132.32(19) . . ?
C8 C7 C12 115.50(18) . . ?
C8 C7 C6 117.90(18) . . ?
C12 C7 C6 126.51(18) . . ?
C9 C8 C7 123.02(19) . . ?
C8 C9 C10 121.03(19) . . ?
N1 C10 C11 121.71(19) . . ?
N1 C10 C9 122.00(19) . . ?
C11 C10 C9 116.28(18) . . ?
C12 C11 C10 121.91(19) . . ?
C11 C12 C7 122.2(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.15
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/pentane'
_exptl_crystal_preparation       Luminescent
