# 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_4of_ligand
_database_code_depnum_ccdc_archive 'CCDC 1892056'
loop_
_audit_author_name
_audit_author_address
'Hasan Piskin'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2019-01-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H7 F3 N2 O2'
_chemical_formula_sum            'C15 H7 F3 N2 O2'
_chemical_formula_weight         304.23
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.857(3)
_cell_length_b                   8.174(2)
_cell_length_c                   17.195(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.077(18)
_cell_angle_gamma                90
_cell_volume                     1371.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    780
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      2.7641
_cell_measurement_theta_min      21.8723
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.152
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5681
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.087
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1335
_reflns_number_total             2400
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.3835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1608
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O 0.4339(2) 0.0571(3) 0.67493(12) 0.0730(7) Uani 1 1 d . . . . .
O1 O 0.9963(2) 0.1025(3) 0.74034(12) 0.0788(8) Uani 1 1 d . . . . .
C5 C 1.0952(3) -0.1222(3) 0.92464(16) 0.0497(7) Uani 1 1 d . . . . .
C6 C 1.0109(3) -0.0610(4) 0.85920(16) 0.0513(8) Uani 1 1 d . . . . .
C4 C 1.2348(3) -0.0858(4) 0.93630(17) 0.0545(8) Uani 1 1 d . . . . .
C9 C 0.8534(3) 0.0893(4) 0.72618(18) 0.0586(8) Uani 1 1 d . . . . .
C1 C 1.0673(3) 0.0360(4) 0.80705(17) 0.0544(8) Uani 1 1 d . . . . .
C2 C 1.2052(3) 0.0733(4) 0.8186(2) 0.0611(9) Uani 1 1 d . . . . .
C7 C 1.3218(3) -0.1498(4) 1.00334(19) 0.0669(9) Uani 1 1 d . . . . .
C11 C 0.6331(4) 0.1645(4) 0.75296(18) 0.0630(9) Uani 1 1 d . . . . .
C14 C 0.7969(4) 0.0000(4) 0.6617(2) 0.0649(9) Uani 1 1 d . . . . .
C8 C 1.0378(3) -0.2190(4) 0.98166(19) 0.0577(8) Uani 1 1 d . . . . .
C13 C 0.6566(3) -0.0069(4) 0.64365(19) 0.0633(9) Uani 1 1 d . . . . .
C12 C 0.5778(3) 0.0752(4) 0.68921(17) 0.0546(8) Uani 1 1 d . . . . .
C15 C 0.3640(4) 0.1523(6) 0.6218(2) 0.0828(11) Uani 1 1 d . . . . .
F2 F 0.2354(2) 0.1151(4) 0.61587(15) 0.1423(12) Uani 1 1 d . . . . .
N1 N 1.3935(3) -0.1989(4) 1.05618(17) 0.0925(10) Uani 1 1 d . . . . .
C10 C 0.7735(4) 0.1729(5) 0.7714(2) 0.0659(10) Uani 1 1 d . . . . .
C3 C 1.2886(3) 0.0104(4) 0.88269(19) 0.0649(9) Uani 1 1 d . . . . .
F3 F 0.4006(3) 0.1424(5) 0.55378(14) 0.1572(14) Uani 1 1 d . . . . .
N2 N 0.9953(3) -0.2911(4) 1.02936(18) 0.0847(9) Uani 1 1 d . . . . .
F1 F 0.3721(4) 0.3032(4) 0.6418(2) 0.1785(16) Uani 1 1 d . . . . .
H6 H 0.914(3) -0.086(3) 0.8529(16) 0.060(8) Uiso 1 1 d . . . . .
H2 H 1.243(3) 0.140(4) 0.7814(18) 0.069(10) Uiso 1 1 d . . . . .
H13 H 0.615(3) -0.078(4) 0.599(2) 0.089(11) Uiso 1 1 d . . . . .
H3 H 1.383(3) 0.038(4) 0.8869(17) 0.074(10) Uiso 1 1 d . . . . .
H14 H 0.859(3) -0.051(4) 0.6355(18) 0.068(10) Uiso 1 1 d . . . . .
H11 H 0.580(3) 0.222(4) 0.7840(18) 0.066(9) Uiso 1 1 d . . . . .
H10 H 0.810(4) 0.233(4) 0.810(2) 0.089(12) 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
O2 C12 1.413(3) . ?
O2 C15 1.318(4) . ?
O1 C9 1.399(4) . ?
O1 C1 1.370(3) . ?
C5 C6 1.394(4) . ?
C5 C4 1.394(4) . ?
C5 C8 1.436(5) . ?
C6 C1 1.372(4) . ?
C4 C7 1.435(4) . ?
C4 C3 1.374(4) . ?
C9 C14 1.378(5) . ?
C9 C10 1.366(5) . ?
C1 C2 1.380(4) . ?
C2 C3 1.378(4) . ?
C7 N1 1.143(4) . ?
C11 C12 1.365(4) . ?
C11 C10 1.377(5) . ?
C14 C13 1.375(5) . ?
C8 N2 1.137(4) . ?
C13 C12 1.356(4) . ?
C15 F2 1.294(4) . ?
C15 F3 1.275(4) . ?
C15 F1 1.280(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
C15 O2 C12 118.3(3) . . ?
C1 O1 C9 119.9(2) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 C8 120.1(3) . . ?
C4 C5 C8 119.6(3) . . ?
C1 C6 C5 119.0(3) . . ?
C5 C4 C7 120.3(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 C7 120.2(3) . . ?
C14 C9 O1 117.7(3) . . ?
C10 C9 O1 120.6(3) . . ?
C10 C9 C14 121.5(3) . . ?
O1 C1 C6 124.8(3) . . ?
O1 C1 C2 114.2(3) . . ?
C6 C1 C2 121.0(3) . . ?
C3 C2 C1 119.9(3) . . ?
N1 C7 C4 178.5(4) . . ?
C12 C11 C10 119.1(3) . . ?
C13 C14 C9 118.9(3) . . ?
N2 C8 C5 176.9(3) . . ?
C12 C13 C14 119.2(3) . . ?
C11 C12 O2 118.2(3) . . ?
C13 C12 O2 119.4(3) . . ?
C13 C12 C11 122.2(3) . . ?
F2 C15 O2 109.1(4) . . ?
F3 C15 O2 114.2(4) . . ?
F3 C15 F2 108.3(3) . . ?
F3 C15 F1 107.0(4) . . ?
F1 C15 O2 112.1(3) . . ?
F1 C15 F2 105.8(4) . . ?
C9 C10 C11 119.1(3) . . ?
C4 C3 C2 120.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
