# 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 2019

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1906087'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN-CNRS University Paris Saclay
France
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_compound_b          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Only tiny crystals were available and required highly powerful
copper radiation to get useful diffraction signal. However despite
reasonably long exposure, the resolution barely reached atomic level 
(0.8\%A is the accessible limit to the Rigaku experimental setup)
and decision was taken to apply a cut-off to the dataset
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        
1-(4-(5-(trifluoromethyl)imidazo[1,2-a]pyrimidin-7-yl)phenyl)ethan-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 F3 N3 O'
_chemical_formula_sum            'C15 H10 F3 N3 O'
_chemical_formula_weight         305.26

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'
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'

_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                   13.2871(6)
_cell_length_b                   7.3989(4)
_cell_length_c                   14.1570(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.735(7)
_cell_angle_gamma                90
_cell_volume                     1346.00(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2621
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      64.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku mm007 HF'
_diffrn_detector                 'Rigaku Rapid-2 curved IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            6060
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.439
_diffrn_reflns_theta_max         60.021
_diffrn_reflns_theta_full        60.021
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1939
_reflns_number_gt                862
_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXD (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0759P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         1939
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1778
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_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
N1 N 0.3106(2) 0.5939(4) 0.2204(2) 0.0551(9) Uani 1 1 d . . . . .
F1 F 0.47603(18) 0.6872(4) 0.1235(2) 0.1107(11) Uani 1 1 d . . . . .
O1 O -0.3312(2) 0.9526(5) -0.1423(2) 0.0987(12) Uani 1 1 d . . . . .
C1 C 0.3381(4) 0.5756(6) 0.3769(3) 0.0799(14) Uani 1 1 d . . . . .
H1 H 0.371782 0.558483 0.442352 0.096 Uiso 1 1 calc R U . . .
N2 N 0.1290(2) 0.6754(4) 0.1856(2) 0.0616(10) Uani 1 1 d . . . . .
F2 F 0.45023(18) 0.4088(4) 0.13209(19) 0.1046(11) Uani 1 1 d . . . . .
C2 C 0.3864(3) 0.5599(6) 0.3041(3) 0.0672(12) Uani 1 1 d . . . . .
H2 H 0.455964 0.532087 0.309637 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3068(3) 0.5999(5) 0.1224(3) 0.0550(11) Uani 1 1 d . . . . .
F3 F 0.38962(19) 0.5472(4) -0.00104(19) 0.1209(12) Uani 1 1 d . . . . .
N3 N 0.2354(3) 0.6190(5) 0.3453(2) 0.0746(11) Uani 1 1 d . . . . .
C4 C 0.2167(3) 0.6435(5) 0.0584(3) 0.0585(12) Uani 1 1 d . . . . .
H4 H 0.213299 0.648372 -0.007951 0.070 Uiso 1 1 calc R U . . .
C14 C -0.2589(4) 0.9043(6) -0.1741(3) 0.0689(12) Uani 1 1 d . . . . .
C5 C 0.1265(3) 0.6822(5) 0.0916(3) 0.0533(11) Uani 1 1 d . . . . .
C6 C 0.2190(3) 0.6300(5) 0.2494(3) 0.0606(12) Uani 1 1 d . . . . .
C15 C -0.2691(3) 0.9109(6) -0.2826(3) 0.0901(15) Uani 1 1 d . . . . .
H15A H -0.265317 0.790466 -0.306744 0.135 Uiso 1 1 calc R U . . .
H15B H -0.213781 0.982505 -0.295309 0.135 Uiso 1 1 calc R U . . .
H15C H -0.334863 0.963786 -0.314859 0.135 Uiso 1 1 calc R U . . .
C8 C 0.0174(3) 0.7425(6) -0.0775(3) 0.0729(14) Uani 1 1 d . . . . .
H8 H 0.073807 0.712543 -0.102206 0.087 Uiso 1 1 calc R U . . .
C7 C 0.0278(3) 0.7328(5) 0.0216(3) 0.0535(11) Uani 1 1 d . . . . .
C12 C -0.0588(3) 0.7766(6) 0.0547(3) 0.0706(13) Uani 1 1 d . . . . .
H12 H -0.054665 0.770369 0.121195 0.085 Uiso 1 1 calc R U . . .
C9 C -0.0745(3) 0.7954(6) -0.1409(3) 0.0736(14) Uani 1 1 d . . . . .
H9 H -0.078894 0.801512 -0.207465 0.088 Uiso 1 1 calc R U . . .
C11 C -0.1505(3) 0.8288(6) -0.0087(3) 0.0756(14) Uani 1 1 d . . . . .
H11 H -0.207281 0.857658 0.015647 0.091 Uiso 1 1 calc R U . . .
C10 C -0.1599(3) 0.8393(5) -0.1076(3) 0.0558(11) Uani 1 1 d . . . . .
C13 C 0.4061(4) 0.5602(8) 0.0943(3) 0.0748(14) 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
N1 C2 1.370(4) . ?
N1 C3 1.375(4) . ?
N1 C6 1.406(4) . ?
F1 C13 1.312(5) . ?
O1 C14 1.215(5) . ?
C1 C2 1.350(5) . ?
C1 N3 1.362(5) . ?
N2 C5 1.324(4) . ?
N2 C6 1.344(4) . ?
F2 C13 1.313(5) . ?
C3 C4 1.344(4) . ?
C3 C13 1.501(5) . ?
F3 C13 1.315(4) . ?
N3 C6 1.321(4) . ?
C4 C5 1.424(5) . ?
C14 C10 1.489(5) . ?
C14 C15 1.507(5) . ?
C5 C7 1.476(5) . ?
C8 C9 1.376(5) . ?
C8 C7 1.377(4) . ?
C7 C12 1.387(4) . ?
C12 C11 1.372(5) . ?
C9 C10 1.373(5) . ?
C11 C10 1.377(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
C2 N1 C3 135.1(4) . . ?
C2 N1 C6 106.5(3) . . ?
C3 N1 C6 118.4(3) . . ?
C2 C1 N3 113.6(4) . . ?
C5 N2 C6 118.4(3) . . ?
C1 C2 N1 104.9(4) . . ?
C4 C3 N1 119.0(4) . . ?
C4 C3 C13 124.1(4) . . ?
N1 C3 C13 116.9(4) . . ?
C6 N3 C1 104.0(4) . . ?
C3 C4 C5 120.4(4) . . ?
O1 C14 C10 121.0(4) . . ?
O1 C14 C15 119.6(4) . . ?
C10 C14 C15 119.4(4) . . ?
N2 C5 C4 121.1(4) . . ?
N2 C5 C7 118.4(3) . . ?
C4 C5 C7 120.5(3) . . ?
N3 C6 N2 126.3(4) . . ?
N3 C6 N1 111.0(4) . . ?
N2 C6 N1 122.7(3) . . ?
C9 C8 C7 121.5(4) . . ?
C8 C7 C12 117.1(4) . . ?
C8 C7 C5 122.6(4) . . ?
C12 C7 C5 120.2(3) . . ?
C11 C12 C7 121.3(4) . . ?
C10 C9 C8 121.2(4) . . ?
C12 C11 C10 121.1(4) . . ?
C9 C10 C11 117.9(4) . . ?
C9 C10 C14 122.2(4) . . ?
C11 C10 C14 119.9(4) . . ?
F1 C13 F2 106.0(4) . . ?
F1 C13 F3 107.2(4) . . ?
F2 C13 F3 107.3(4) . . ?
F1 C13 C3 112.1(4) . . ?
F2 C13 C3 113.0(4) . . ?
F3 C13 C3 111.0(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
N3 C1 C2 N1 -0.4(5) . . . . ?
C3 N1 C2 C1 -179.9(4) . . . . ?
C6 N1 C2 C1 0.3(4) . . . . ?
C2 N1 C3 C4 -178.3(4) . . . . ?
C6 N1 C3 C4 1.4(5) . . . . ?
C2 N1 C3 C13 0.4(6) . . . . ?
C6 N1 C3 C13 -179.8(4) . . . . ?
C2 C1 N3 C6 0.2(5) . . . . ?
N1 C3 C4 C5 -0.2(6) . . . . ?
C13 C3 C4 C5 -178.9(4) . . . . ?
C6 N2 C5 C4 -0.4(6) . . . . ?
C6 N2 C5 C7 -179.7(4) . . . . ?
C3 C4 C5 N2 -0.3(6) . . . . ?
C3 C4 C5 C7 179.0(4) . . . . ?
C1 N3 C6 N2 -177.8(4) . . . . ?
C1 N3 C6 N1 0.0(5) . . . . ?
C5 N2 C6 N3 179.1(4) . . . . ?
C5 N2 C6 N1 1.6(6) . . . . ?
C2 N1 C6 N3 -0.2(5) . . . . ?
C3 N1 C6 N3 180.0(3) . . . . ?
C2 N1 C6 N2 177.7(4) . . . . ?
C3 N1 C6 N2 -2.1(5) . . . . ?
C9 C8 C7 C12 0.8(6) . . . . ?
C9 C8 C7 C5 -178.0(4) . . . . ?
N2 C5 C7 C8 -179.6(4) . . . . ?
C4 C5 C7 C8 1.1(6) . . . . ?
N2 C5 C7 C12 1.6(5) . . . . ?
C4 C5 C7 C12 -177.7(4) . . . . ?
C8 C7 C12 C11 -0.6(6) . . . . ?
C5 C7 C12 C11 178.2(4) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C7 C12 C11 C10 0.2(7) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C8 C9 C10 C14 177.4(4) . . . . ?
C12 C11 C10 C9 0.1(7) . . . . ?
C12 C11 C10 C14 -177.3(4) . . . . ?
O1 C14 C10 C9 -175.6(4) . . . . ?
C15 C14 C10 C9 4.2(6) . . . . ?
O1 C14 C10 C11 1.7(6) . . . . ?
C15 C14 C10 C11 -178.5(4) . . . . ?
C4 C3 C13 F1 110.4(5) . . . . ?
N1 C3 C13 F1 -68.3(5) . . . . ?
C4 C3 C13 F2 -129.9(4) . . . . ?
N1 C3 C13 F2 51.4(6) . . . . ?
C4 C3 C13 F3 -9.4(7) . . . . ?
N1 C3 C13 F3 171.9(4) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
