# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1473665'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-trifluoromethylchromone-3-cyanide-methyl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 F3 N O2'
_chemical_formula_weight         253.18

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6164(8)
_cell_length_b                   19.798(2)
_cell_length_c                   7.849(1)
_cell_angle_alpha                90
_cell_angle_beta                 114.01(1)
_cell_angle_gamma                90
_cell_volume                     1081.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1192
_cell_measurement_theta_min      4.4629
_cell_measurement_theta_max      73.3340
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.387
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    1.242
_shelx_estimated_absorpt_T_min   0.494
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_T_min  0.70458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4180
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.467
_diffrn_reflns_theta_max         73.491
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2142
_reflns_number_gt                1543
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+0.0304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2142
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5226(4) 0.61690(12) 0.8591(3) 0.0640(6) Uani 1 1 d . . . . .
C2 C 0.3615(4) 0.63260(13) 0.8910(3) 0.0669(6) Uani 1 1 d . . . . .
C3 C 0.2143(3) 0.58727(12) 0.8502(3) 0.0599(6) Uani 1 1 d . . . . .
C4 C 0.2257(3) 0.52383(10) 0.7751(3) 0.0484(5) Uani 1 1 d . . . . .
C5 C 0.0704(3) 0.47418(11) 0.7263(3) 0.0532(5) Uani 1 1 d . . . . .
C6 C 0.1100(3) 0.40882(10) 0.6608(3) 0.0481(5) Uani 1 1 d . . . . .
C7 C 0.2753(3) 0.40057(10) 0.6410(3) 0.0473(4) Uani 1 1 d . . . . .
C8 C 0.3891(3) 0.50928(10) 0.7463(3) 0.0474(5) Uani 1 1 d . . . . .
C9 C 0.5393(3) 0.55446(12) 0.7868(3) 0.0576(5) Uani 1 1 d . . . . .
C10 C 0.3332(3) 0.33627(11) 0.5738(3) 0.0591(5) Uani 1 1 d . . . . .
C11 C -0.0448(3) 0.35526(12) 0.6147(3) 0.0555(5) Uani 1 1 d . . . . .
C12 C -0.0484(3) 0.32549(11) 0.7838(3) 0.0568(5) Uani 1 1 d . . . . .
N N -0.0511(3) 0.30170(12) 0.9142(3) 0.0802(7) Uani 1 1 d . . . . .
O1 O 0.41269(19) 0.44770(7) 0.67573(19) 0.0517(4) Uani 1 1 d . . . . .
O2 O -0.0824(2) 0.48501(9) 0.7380(3) 0.0770(5) Uani 1 1 d . . . . .
F1 F 0.2186(2) 0.32285(8) 0.3984(2) 0.0823(5) Uani 1 1 d . . . . .
F2 F 0.3248(2) 0.28388(7) 0.6750(2) 0.0862(5) Uani 1 1 d . . . . .
F3 F 0.5102(2) 0.33913(8) 0.5828(3) 0.0917(6) Uani 1 1 d . . . . .
H1 H 0.625(4) 0.6477(14) 0.881(3) 0.070(7) Uiso 1 1 d . . . . .
H2 H 0.352(4) 0.6740(14) 0.939(3) 0.077(8) Uiso 1 1 d . . . . .
H3 H 0.097(4) 0.5945(13) 0.874(3) 0.073(7) Uiso 1 1 d . . . . .
H9 H 0.653(3) 0.5406(12) 0.771(3) 0.060(6) Uiso 1 1 d . . . . .
H11A H -0.031(4) 0.3193(15) 0.530(4) 0.083(8) Uiso 1 1 d . . . . .
H11B H -0.166(4) 0.3780(12) 0.552(3) 0.068(7) 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
C1 C2 1.384(4) . ?
C1 C9 1.388(3) . ?
C2 C3 1.369(3) . ?
C3 C4 1.405(3) . ?
C4 C8 1.383(3) . ?
C4 C5 1.465(3) . ?
C5 O2 1.222(3) . ?
C5 C6 1.468(3) . ?
C6 C7 1.339(3) . ?
C6 C11 1.516(3) . ?
C7 O1 1.345(2) . ?
C7 C10 1.511(3) . ?
C8 O1 1.381(2) . ?
C8 C9 1.383(3) . ?
C10 F3 1.322(3) . ?
C10 F1 1.323(3) . ?
C10 F2 1.324(3) . ?
C11 C12 1.463(3) . ?
C12 N 1.134(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
C2 C1 C9 120.6(2) . . ?
C3 C2 C1 120.8(2) . . ?
C2 C3 C4 120.0(2) . . ?
C8 C4 C3 117.9(2) . . ?
C8 C4 C5 120.16(19) . . ?
C3 C4 C5 121.9(2) . . ?
O2 C5 C4 123.7(2) . . ?
O2 C5 C6 121.2(2) . . ?
C4 C5 C6 115.08(17) . . ?
C7 C6 C5 119.00(18) . . ?
C7 C6 C11 124.28(19) . . ?
C5 C6 C11 116.70(18) . . ?
C6 C7 O1 125.63(19) . . ?
C6 C7 C10 124.41(19) . . ?
O1 C7 C10 109.96(17) . . ?
O1 C8 C4 121.48(18) . . ?
O1 C8 C9 115.66(19) . . ?
C4 C8 C9 122.9(2) . . ?
C8 C9 C1 117.7(2) . . ?
F3 C10 F1 106.92(19) . . ?
F3 C10 F2 107.4(2) . . ?
F1 C10 F2 107.11(19) . . ?
F3 C10 C7 112.45(18) . . ?
F1 C10 C7 111.68(18) . . ?
F2 C10 C7 111.01(18) . . ?
C12 C11 C6 111.44(18) . . ?
N C12 C11 179.2(3) . . ?
C7 O1 C8 118.46(15) . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1473667'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-trifluoromethylchromone-3-oxydryl-methyl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 F3 O3'
_chemical_formula_weight         244.17

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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                   4.7865(2)
_cell_length_b                   15.3885(6)
_cell_length_c                   13.7073(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.722(3)
_cell_angle_gamma                90
_cell_volume                     1007.51(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2582
_cell_measurement_theta_min      3.2570
_cell_measurement_theta_max      72.2740
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    1.350
_shelx_estimated_absorpt_T_min   0.545
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_T_min  0.66087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            6524
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.325
_diffrn_reflns_theta_max         72.418
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1959
_reflns_number_gt                1662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
The trifluoromethyl group showed severe rotational disorder around the C-CF3 
bond which could be modeled in terms of four angularly split replicas. 
These were refined with isotropic displacement parameters for the fluorine 
atoms and restraining the C-F bond lengths and F...F distances to be 
respectively equal to one another while keeping the sum of the occupancies 
equal to one
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²+0.4164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     207
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1759
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.405
_refine_ls_shift/su_max          0.008
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4128(6) 0.31450(17) 0.7022(2) 0.0697(7) Uani 1 1 d . . . . .
C2 C -0.4230(6) 0.29266(17) 0.6034(2) 0.0693(7) Uani 1 1 d . . . . .
C3 C -0.2530(5) 0.22886(16) 0.5709(2) 0.0596(6) Uani 1 1 d . . . . .
C4 C -0.0677(4) 0.18467(14) 0.63697(16) 0.0483(5) Uani 1 1 d . . . . .
C5 C 0.1132(4) 0.11520(14) 0.60632(15) 0.0491(5) Uani 1 1 d . . . . .
C6 C 0.2855(4) 0.07158(13) 0.68370(16) 0.0474(5) Uani 1 1 d . . . . .
C7 C 0.2711(4) 0.09982(14) 0.77636(16) 0.0498(5) Uani 1 1 d . . . . .
C8 C -0.0609(4) 0.20789(13) 0.73530(16) 0.0491(5) Uani 1 1 d . . . . .
C9 C -0.2334(5) 0.27303(16) 0.7686(2) 0.0605(6) Uani 1 1 d . . . . .
C10 C 0.4165(5) 0.06011(17) 0.86648(18) 0.0624(6) Uani 1 1 d D . . . .
C11 C 0.4534(5) -0.00535(17) 0.6525(2) 0.0597(6) Uani 1 1 d . . . . .
O1 O 0.1126(3) 0.16686(10) 0.80402(11) 0.0546(4) Uani 1 1 d . . . . .
O2 O 0.1215(4) 0.09169(13) 0.52074(12) 0.0667(5) Uani 1 1 d . . . . .
O3 O 0.2827(5) -0.07936(11) 0.63876(14) 0.0683(5) Uani 1 1 d . . . . .
F1A F 0.439(2) 0.1129(5) 0.9408(5) 0.0698(19) Uiso 0.311(8) 1 d D . P A 1
F2A F 0.2957(15) -0.0108(6) 0.8895(7) 0.0624(18) Uiso 0.311(8) 1 d D . P A 1
F3A F 0.6970(10) 0.0396(6) 0.8461(4) 0.0555(16) Uiso 0.311(8) 1 d D . P A 1
F1C F 0.225(2) 0.0537(11) 0.9408(7) 0.062(3) Uiso 0.184(6) 1 d D . P A 2
F2C F 0.500(4) -0.0235(7) 0.8580(7) 0.075(3) Uiso 0.184(6) 1 d D . P A 2
F3C F 0.613(3) 0.1040(9) 0.9085(8) 0.069(3) Uiso 0.184(6) 1 d D . P A 2
F1B F 0.312(3) 0.0882(7) 0.9487(5) 0.069(2) Uiso 0.233(7) 1 d D . P A 3
F2B F 0.361(2) -0.0307(4) 0.8647(6) 0.055(2) Uiso 0.233(7) 1 d D . P A 3
F3B F 0.6766(13) 0.0680(7) 0.8710(7) 0.057(2) Uiso 0.233(7) 1 d D . P A 3
F1D F 0.2453(15) 0.0204(9) 0.9203(8) 0.068(2) Uiso 0.272(7) 1 d D . P A 4
F2D F 0.635(2) 0.0093(7) 0.8549(5) 0.070(2) Uiso 0.272(7) 1 d D . P A 4
F3D F 0.535(2) 0.1308(4) 0.9235(5) 0.0608(19) Uiso 0.272(7) 1 d D . P A 4
H H 0.139(8) -0.072(2) 0.590(3) 0.102(12) Uiso 1 1 d . . . . .
H1 H -0.535(7) 0.356(2) 0.726(2) 0.085(9) Uiso 1 1 d . . . . .
H2 H -0.538(7) 0.323(2) 0.557(2) 0.077(9) Uiso 1 1 d . . . . .
H3 H -0.261(6) 0.2123(19) 0.500(2) 0.071(8) Uiso 1 1 d . . . . .
H9 H -0.225(6) 0.2870(19) 0.835(2) 0.066(8) Uiso 1 1 d . . . . .
H11A H 0.607(7) -0.022(2) 0.705(2) 0.076(8) Uiso 1 1 d . . . . .
H11B H 0.547(6) 0.0092(18) 0.590(2) 0.064(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.368(4) . ?
C1 C2 1.394(5) . ?
C2 C3 1.368(4) . ?
C3 C4 1.402(3) . ?
C4 C8 1.393(3) . ?
C4 C5 1.455(3) . ?
C5 O2 1.231(3) . ?
C5 C6 1.464(3) . ?
C6 C7 1.348(3) . ?
C6 C11 1.508(3) . ?
C7 O1 1.349(3) . ?
C7 C10 1.507(3) . ?
C8 O1 1.369(3) . ?
C8 C9 1.394(3) . ?
C10 F3B 1.248(6) . ?
C10 F2A 1.283(6) . ?
C10 F3C 1.266(9) . ?
C10 F1D 1.291(6) . ?
C10 F1A 1.302(6) . ?
C10 F2D 1.324(6) . ?
C10 F1B 1.333(7) . ?
C10 F2C 1.354(9) . ?
C10 F2B 1.423(6) . ?
C10 F3A 1.425(6) . ?
C10 F1C 1.418(8) . ?
C10 F3D 1.434(6) . ?
C11 O3 1.407(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
C9 C1 C2 121.0(2) . . ?
C3 C2 C1 120.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
C8 C4 C3 118.4(2) . . ?
C8 C4 C5 119.4(2) . . ?
C3 C4 C5 122.2(2) . . ?
O2 C5 C4 123.2(2) . . ?
O2 C5 C6 120.3(2) . . ?
C4 C5 C6 116.47(19) . . ?
C7 C6 C5 118.29(19) . . ?
C7 C6 C11 125.5(2) . . ?
C5 C6 C11 116.09(19) . . ?
C6 C7 O1 125.1(2) . . ?
C6 C7 C10 126.3(2) . . ?
O1 C7 C10 108.53(18) . . ?
O1 C8 C4 121.50(19) . . ?
O1 C8 C9 116.9(2) . . ?
C4 C8 C9 121.6(2) . . ?
C1 C9 C8 118.5(3) . . ?
F2A C10 F1A 110.7(5) . . ?
F1D C10 F2D 109.0(5) . . ?
F3B C10 F1B 110.7(6) . . ?
F3C C10 F2C 109.3(8) . . ?
F3B C10 F2B 106.2(5) . . ?
F1B C10 F2B 104.7(5) . . ?
F2A C10 F3A 107.8(5) . . ?
F1A C10 F3A 105.1(4) . . ?
F3C C10 F1C 101.9(7) . . ?
F2C C10 F1C 101.8(7) . . ?
F1D C10 F3D 106.8(6) . . ?
F2D C10 F3D 103.1(5) . . ?
O3 C11 C6 110.97(19) . . ?
C7 O1 C8 119.11(17) . . ?

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
O3 H O2 0.93(4) 1.92(4) 2.830(3) 163(3) 3_556

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Methanol
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1473666'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-trifluoromethylchromone-3-nitro-methyl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 F3 N O4'
_chemical_formula_weight         273.17

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           ?

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.5438(5)
_cell_length_b                   20.2116(11)
_cell_length_c                   7.7385(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.717(9)
_cell_angle_gamma                90
_cell_volume                     1103.61(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    863
_cell_measurement_theta_min      4.3714
_cell_measurement_theta_max      73.0440
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    1.405
_shelx_estimated_absorpt_T_min   0.549
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_T_min  0.79219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4195
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.375
_diffrn_reflns_theta_max         70.959
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2092
_reflns_number_gt                1247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1854P)²+0.2396P] 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-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2092
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.3330
_refine_ls_wR_factor_gt          0.2382
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.010
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3626(7) 0.3907(3) 0.4883(8) 0.0805(16) Uani 1 1 d . . . . .
H1 H 0.3927 0.3601 0.5840 0.097 Uiso 1 1 calc R U . . .
C2 C 0.3967(8) 0.3753(3) 0.3275(9) 0.0849(17) Uani 1 1 d . . . . .
H2 H 0.4489 0.3346 0.3162 0.102 Uiso 1 1 calc R U . . .
C3 C 0.3535(6) 0.4199(3) 0.1866(7) 0.0746(14) Uani 1 1 d . . . . .
H3 H 0.3771 0.4093 0.0798 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2740(6) 0.4815(2) 0.2004(6) 0.0637(12) Uani 1 1 d . . . . .
C5 C 0.2233(6) 0.5300(3) 0.0509(6) 0.0659(13) Uani 1 1 d . . . . .
C6 C 0.1536(6) 0.5937(2) 0.0953(6) 0.0606(11) Uani 1 1 d . . . . .
C7 C 0.1317(6) 0.6016(2) 0.2565(6) 0.0631(12) Uani 1 1 d . . . . .
C8 C 0.2414(6) 0.4949(2) 0.3624(6) 0.0610(12) Uani 1 1 d . . . . .
C9 C 0.2849(7) 0.4507(3) 0.5079(6) 0.0715(13) Uani 1 1 d . . . . .
H9 H 0.2625 0.4611 0.6155 0.086 Uiso 1 1 calc R U . . .
C10 C 0.0587(8) 0.6640(2) 0.3189(7) 0.0738(14) Uani 1 1 d . . . . .
C11 C 0.1107(7) 0.6461(3) -0.0503(7) 0.0698(13) Uani 1 1 d . . . . .
H11A H 0.0204 0.6772 -0.0330 0.084 Uiso 1 1 calc R U . . .
H11B H 0.0529 0.6259 -0.1709 0.084 Uiso 1 1 calc R U . . .
N N 0.2875(6) 0.6831(2) -0.0441(5) 0.0688(11) Uani 1 1 d . . . . .
O1 O 0.1660(4) 0.55515(16) 0.3882(4) 0.0665(10) Uani 1 1 d . . . . .
O2 O 0.2360(6) 0.5194(2) -0.1001(5) 0.0874(12) Uani 1 1 d . . . . .
O3 O 0.4399(5) 0.6670(2) 0.0648(5) 0.0848(12) Uani 1 1 d . . . . .
O4 O 0.2652(7) 0.7282(2) -0.1536(6) 0.1081(16) Uani 1 1 d . . . . .
F1 F -0.1160(5) 0.6775(2) 0.2139(6) 0.1175(15) Uani 1 1 d . . . . .
F2 F 0.1647(6) 0.71532(17) 0.3093(7) 0.1210(15) Uani 1 1 d . . . . .
F3 F 0.0656(7) 0.66039(19) 0.4878(5) 0.1183(15) 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
C1 C9 1.378(8) . ?
C1 C2 1.393(9) . ?
C2 C3 1.361(8) . ?
C3 C4 1.403(7) . ?
C4 C8 1.387(7) . ?
C4 C5 1.461(7) . ?
C5 O2 1.224(6) . ?
C5 C6 1.476(7) . ?
C6 C7 1.324(6) . ?
C6 C11 1.497(6) . ?
C7 O1 1.342(5) . ?
C7 C10 1.523(7) . ?
C8 C9 1.382(6) . ?
C8 O1 1.388(5) . ?
C10 F3 1.292(6) . ?
C10 F1 1.309(6) . ?
C10 F2 1.327(6) . ?
C11 N 1.515(6) . ?
N O3 1.206(5) . ?
N O4 1.215(5) . ?

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 C1 C2 121.0(5) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C4 120.9(5) . . ?
C8 C4 C3 117.4(4) . . ?
C8 C4 C5 120.3(4) . . ?
C3 C4 C5 122.4(5) . . ?
O2 C5 C4 123.4(5) . . ?
O2 C5 C6 122.0(4) . . ?
C4 C5 C6 114.6(4) . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 C11 123.9(4) . . ?
C5 C6 C11 116.2(4) . . ?
C6 C7 O1 125.2(4) . . ?
C6 C7 C10 125.3(4) . . ?
O1 C7 C10 109.4(4) . . ?
C9 C8 C4 122.9(4) . . ?
C9 C8 O1 116.2(4) . . ?
C4 C8 O1 121.0(4) . . ?
C1 C9 C8 117.8(5) . . ?
F3 C10 F1 108.1(5) . . ?
F3 C10 F2 107.0(5) . . ?
F1 C10 F2 107.3(5) . . ?
F3 C10 C7 112.6(4) . . ?
F1 C10 C7 111.9(4) . . ?
F2 C10 C7 109.7(4) . . ?
C6 C11 N 111.8(4) . . ?
O3 N O4 123.6(5) . . ?
O3 N C11 120.0(4) . . ?
O4 N C11 116.4(4) . . ?
C7 O1 C8 118.9(4) . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.084


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Ethanol
